Benzamide compounds and their use as herbicides
阅读说明：本技术 苯甲酰胺化合物及其作为除草剂的用途 (Benzamide compounds and their use as herbicides ) 是由 M·科德斯 T·齐克 T·塞茨 R·L·尼尔森 于 2019-01-07 设计创作，主要内容包括：本发明涉及式(I)的苯甲酰胺化合物、其N-氧化物和盐,其中变量如权利要求书和说明书中所定义。本发明还涉及包含此类化合物的组合物以及此类化合物用于控制不希望的植物生长的用途。<Image he="316" wi="700" file="DDA0002575255360000011.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>(The invention relates to benzamide compounds of formula (I), N-oxides and salts thereof, wherein the variables are as defined in the claims and specificationAs defined in the specification. The invention also relates to compositions comprising such compounds and to the use of such compounds for controlling undesired plant growth.)
1. A compound of formula I, an N-oxide or an agriculturally acceptable salt thereof,
wherein
Q is selected from the formula Q1、Q2、Q3And Q4A group of (a);
wherein in the formula Q1、Q2、Q3And Q4# in (a) represents the point of attachment to the nitrogen atom;
R1selected from cyano, halogen, nitro, C1-C8Alkyl radical, C2-C8-alkenyl, C2-C8-alkynyl, C1-C8-haloalkyl group, C1-C4-alkoxy-C1-C4Alkyl radical, C1-C4-haloalkoxy-C1-C4Alkyl radical, C1-C8-alkoxy, C1-C4-alkoxy-C1-C4-alkoxy-Z1-、C1-C6-haloalkoxy and R1b-S(O)k-Z1-；
R2aSelected from hydrogen, C1-C6Alkyl radical, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkylamino, di-C1-C6-alkylamino radical, C3-C10-cycloalkyl and C3-C10-cycloalkyl-C1-C4Alkyl, in which the alkyl, alkoxy, alkenyl, alkynyl and cycloalkyl moieties of the aforementioned eight groups are unsubstituted, partially or fully halogenated, or substituted by 1 or 2 radicals R2fAnd wherein said cycloalkyl moiety may also be fused to a phenyl ring, said phenyl ring being unsubstituted or 1,2,3 or 4Identical or different radicals R21The substitution is carried out by the following steps,
R2amay also be selected from phenyl and heterocyclyl, where heterocyclyl is a 5-or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1,2,3 or 4 heteroatoms selected from O, N and S as ring members, where phenyl and heterocyclyl are unsubstituted or substituted by 1,2,3 or 4 identical or different radicals R21Substitution;
R2bselected from hydrogen, C1-C6Alkyl radical, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, wherein the alkyl, alkenyl, alkynyl and cycloalkyl moieties of the five aforementioned groups are unsubstituted, partially or fully halogenated, or substituted by 1 or 2 groups R2fSubstitution;
R2bmay also be selected from phenyl and heterocyclyl, where heterocyclyl is a 5-or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1,2,3 or 4 heteroatoms selected from O, N and S as ring members, where phenyl and heterocyclyl are unsubstituted or substituted by 1,2,3 or 4 identical or different radicals R21Substitution;
or
R2aAnd R2bTogether with the nitrogen atom to which they are attached, may form a 4-, 5-, 6-, 7-or 8-membered saturated or partially unsaturated heterocyclic radical which may contain as ring members a further heteroatom selected from O, S and N, and wherein the heterocyclic radical is unsubstituted or carries 1,2,3 or 4 radicals R2dOr with 1 radical R2eAnd 0, 1,2 or 3 radicals R2d，
R2cSelected from hydrogen, C1-C6Alkyl radical, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkylamino, di-C1-C6-alkylamino radical, C3-C10-cycloalkyl and C3-C10-cycloalkyl-C1-C4Alkyl, where the aforementioned seven groups of alkyl, alkenyl, alkynyl and cycloalkylPart being unsubstituted, partially or fully halogenated or substituted by 1 or 2 radicals R2fSubstituted and wherein the cycloalkyl moieties may also be fused to a benzene ring which is unsubstituted or substituted by 1,2,3 or 4 identical or different radicals R21The substitution is carried out by the following steps,
R2cmay also be selected from phenyl and heterocyclyl, where heterocyclyl is a 5-or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1,2,3 or 4 heteroatoms selected from O, N and S as ring members, where phenyl and heterocyclyl are unsubstituted or substituted by 1,2,3 or 4 identical or different radicals R21Substitution;
R2dare identical or different and are selected from halogen, CN, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4Haloalkoxy, or two radicals R attached to adjacent carbon atoms2dMay together form a fused-on benzene ring which is unsubstituted or substituted by 1,2,3 or 4 identical or different radicals R21Substitution;
R2eis selected from ═ O, OH and R4b-S(O)k-Z4-、R4c-C(O)-Z4-、R4dO-C(O)-Z4-、R4eR4fN-C(O)-Z4-、R4gR4hN-Z4-and R4eR4fNS(O)2-Z4-；
R2fSelected from OH, CN, NH2SH, SCN, nitro, tri (C)1-C4Alkyl) silyl group, C1-C4-alkoxy, C1-C4-haloalkoxy, R3eR3fN-、R3c-C(O)-、HO-C(O)-R3dO-C(O)-、R3dS-C(O)-、R3eR3fN-C(O)-、R3eR3fN-NR3h-C(O)-、R3c-C(S)-、R3dO-C(S)-、R3dS-C(S)-、R3eR3fN-C(S)、R3c-S(O)n-、R3c-S(O)2-O-、R3dO-S(O)2-、R3eR3fNS(O)2-、R3c-C(O)-NR3g-、R3dO-C(O)-NR3g-、R3eR3fN-C(O)-NR3g-、R3eR3fN-NR3h-C(O)-NR3g-、R3dO-S(O)2-NR3g-、R3eR3fNS(O)2-NR3g-、R3c-C(O)-NR3g-C(O)-、R3dO-C(O)-NR3g-C(O)-、R3eR3fN-C(O)-NR3g-C(O)-、R3dO-S(O)2-NR3g-C(O)-、R3eR3fNS(O)2-NR3g-C(O)-、R3c-C(O)-NR3g-S(O)2-、R3dO-C(O)-NR3g-S(O)2-、R3eR3fN-C(O)-NR3g-S(O)2-、(OH)2P(O)-、(C1-C4-alkoxy groups)2P(O)-、R3dO-N ═ CH-, phenyl-X and heterocyclyl-X, where heterocyclyl in the last two mentioned groups is a 5-or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1,2,3 or 4 heteroatoms selected from O, N and S as ring members, where phenyl and heterocyclyl are unsubstituted or are substituted by 1,2,3 or 4 identical or different groups R11Substitution;
R3selected from hydrogen, cyano, thiocyanato, halogen, nitro, hydroxy-Z3-、C1-C6Alkyl radical, C2-C8-alkenyl, C2-C8-alkynyl, C3-C10-cycloalkyl-Z3-、C3-C6-cycloalkenyl-Z3-、C3-C10-cycloalkoxy-Z3-、C3-C10-cycloalkyl-C1-C2-alkoxy, wherein the cyclic groups of the four above groups are unsubstituted or partially or fully halogenated; c1-C4Cyanoalkyl, C1-C8-haloalkyl group, C2-C8-haloalkenyl, C3-C8-haloalkynyl, C1-C8-alkoxy-Z3-、C1-C8-haloalkoxy-Z3-、C1-C4-alkoxy-C1-C4-alkoxy-Z3-、C1-C4-haloalkoxy-C1-C4-alkoxy-Z3-、C2-C8-alkenyloxy-Z3-、C2-C8-alkynyloxy-Z3-、C2-C8-haloalkenyloxy-Z3-、C3-C8-haloalkynyloxy-Z3-、R3b-S(O)k-Z3-、R3c-C(O)-Z3-、R3dO-C(O)-Z3-、R3dO-N＝CH-Z3-、R3eR3fN-C(O)-Z3-、R3gR3hN-Z3-、R22C(O)O-Z3-、R25OC(O)O-Z3-、(R22)2NC(O)O-Z3-、R25S(O)2O-Z3-、R22OS(O)2-Z3-、(R22)2NS(O)2-Z3-、R25OC(O)N(R22)-Z3-、(R22)2NC(O)N(R22)-Z3-、(R22)2NS(O)2N(R22)-Z3-、(OH)2P(O)-Z3-、(C1-C4-alkoxy groups)2P(O)-Z3-, phenyl-Z3a-and heterocyclyl-Z3a-, wherein heterocyclyl is a 3-, 4-, 5-or 6-membered monocyclic or 8-, 9-or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle which contains 1,2,3 or 4 heteroatoms from the group consisting of O, N and S as ring members, wherein phenyl-Z is phenyl3a-and heterocyclyl-Z3aThe cyclic groups in (A) are unsubstituted or substituted by 1,2,3 or 4 identical or different radicals R21Substitution;
R4selected from hydrogen, halogen, cyano-Z1、C1-C8Alkyl, nitro, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, wherein C in the two preceding groups3-C7-cycloalkyl is unsubstituted or partially or fully halogenated; c2-C8-alkenyl, C2-C8-alkynyl, C1-C8-haloalkyl group, C1-C3-alkylamino radical, C1-C3-dialkylamino radical, C1-C3-alkylamino-S (O)k、C1-C3-alkylcarbonyl group, C1-C8-alkoxy, C1-C4-alkoxy-C1-C4Alkyl radical, C1-C4-alkoxy-C1-C4-alkoxy-Z1-、C1-C4-alkylthio-C1-C4-alkylthio-Z1-、C2-C6Alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy, C1-C4-haloalkoxy-C1-C4Alkyl radical, C1-C4-haloalkoxy-C1-C4-alkoxy-Z1-、R1b-S(O)k-Z1-, phenoxy-Z1And heterocyclyloxy-Z1-, wherein heterocyclyloxy is an oxygen-bonded 5-or 6-membered monocyclic or 8-, 9-or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle which contains 1,2,3 or 4 heteroatoms from the group consisting of O, N and S as ring members, wherein the cyclic groups in phenoxy and heterocyclyloxy are unsubstituted or substituted by 1,2,3 or 4 identical or different radicals R11Substitution;
R5selected from hydrogen, halogen, cyano-Z1-, nitro, C1-C8Alkyl radical, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, wherein C in the two preceding groups3-C7-cycloalkyl is unsubstituted or partially or fully halogenated; c2-C8-alkenyl, C2-C8-alkynyl, C1-C8-haloalkyl group, C1-C3-alkylamino radical, C1-C3-dialkylamino radical, C1-C3-alkylamino-S(O)k、C1-C3-alkylcarbonyl group, C1-C8-alkoxy, C1-C4-alkoxy-C1-C4Alkyl radical, C1-C4-alkoxy-C1-C4-alkoxy-Z1-、C1-C4-alkylthio-C1-C4Alkyl radical, C1-C4-alkylthio-C1-C4-alkylthio-Z1-、C2-C6Alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy, C1-C4-haloalkoxy-C1-C4Alkyl radical, C1-C4-haloalkoxy-C1-C4-alkoxy-Z1-、R1b-S(O)k-Z1-, phenoxy-Z1And heterocyclyloxy-Z1-, wherein heterocyclyloxy is a 5-or 6-membered monocyclic or 8-, 9-or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle which is linked via an oxygen atom and contains 1,2,3 or 4 heteroatoms from the group O, N and S as ring members, wherein the cyclic radicals phenoxy and heterocyclyloxy are unsubstituted or substituted by 1,2,3 or 4 identical or different radicals R11Substitution;
R6a、R6b、R6c、R6dindependently of one another select C1-C6Alkyl radical, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, wherein C of the two preceding groups3-C7-cycloalkyl is unsubstituted or partially or fully halogenated; c1-C6-haloalkyl group, C2-C6-alkenyl, C2-C6-alkynyl, C2-C6-haloalkenyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4Alkyl radical, C1-C4-haloalkoxy-C1-C4-alkyl, Rb-S(O)n-C1-C3Alkyl, phenyl and benzyl, where phenyl and benzylUnsubstituted or 1,2,3 or 4 are the same or different and are selected from halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-a group substitution of haloalkoxy;
R7selected from hydrogen, CN, NH2、C1-C6Alkyl radical, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, wherein C of the two preceding groups3-C7-cycloalkyl is unsubstituted or partially or fully halogenated; c1-C6-haloalkyl group, C2-C6-alkenyl, C2-C6-alkynyl, C2-C6-haloalkenyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4Alkyl radical, C1-C4-haloalkoxy-C1-C4Alkyl radical, C1-C4-cyanoalkyl, R3b-S(O)k-Z3b-、R3c-C(O)-Z3b-、R3dO-C(O)-Z3b-、R3dO-N＝CH-Z3b-、R3eR3fN-C(O)-Z3b-、R3gR3hN-Z3b-、R22C(O)O-Z3b-、R25OC(O)O-Z3b-、(R22)2NC(O)O-Z3b-、R25S(O)2O-Z3b-、R22OS(O)2-Z3b-、(R22)2NS(O)2-Z3b-、R25OC(O)N(R22)-Z3b-、(R22)2NC(O)N(R22)-Z3b-、(R22)2NS(O)2N(R22)-Z3b-、(OH)2P(O)-Z3b-、(C1-C4-alkoxy groups)2P(O)-Z3b-, phenyl-Z3a-and heterocyclyl-Z3a-, where the heterocyclic group is a 3-, 4-, 5-or 6-membered monocyclic or 8-, 9-or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocyclic ringContaining 1,2,3 or 4 heteroatoms selected from O, N and S as ring members, wherein phenyl-Z3a-and heterocyclyl-Z3aThe cyclic groups in (A) are unsubstituted or substituted by 1,2,3 or 4 identical or different radicals R21Substitution;
R11、R21independently of one another, from cyano, OH, halogen, nitro, C1-C6Alkyl radical, C3-C7-cycloalkyl, C3-C7-halocycloalkyl, C1-C6-haloalkyl group, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C6-alkoxy, C1-C4-alkoxy-C1-C4Alkyl radical, C1-C4-alkylthio-C1-C4Alkyl radical, C1-C4-haloalkoxy-C1-C4Alkyl radical, C1-C4-alkoxy-C1-C4-alkoxy, C3-C7Cycloalkoxy and C1-C6Haloalkoxy, or two radicals R each bound to the same carbon atom11Or R21May together form a group ═ O, or two R groups each bound to an adjacent carbon atom11Or R21May together form a radical selected from C3-C5Alkylene, O-C2-C4Alkylene and O- (C)1-C3-alkylene) -O-;
Z1、Z3、Z4independently of one another, from covalent bonds and unsubstituted, partially or completely fluorinated C1-C4-an alkanediyl group;
Z2is a covalent bond or is selected from C1-C4Alkanediyl and C1-C4-alkanediyl-O-C1-C4-a divalent radical of an alkanediyl radical,
wherein in the last two mentioned radicals, C1-C4-alkanediyl is linear, and wherein C1-C4Alkanediyl is unsubstitutedOr partially or completely fluorinated or substituted by 1,2,3 or 4 radicals RzThe substitution is carried out by the following steps,
Z3aselected from covalent bond, C1-C4Alkanediyl, O-C1-C4Alkanediyl, C1-C4alkanediyl-O and C1-C4-alkanediyl-O-C1-C4-an alkanediyl group;
Z3bis selected from C1-C4Alkanediyl, C1-C4alkanediyl-O and C1-C4-alkanediyl-O-C1-C4-an alkanediyl group;
Rzare identical or different and are selected from C1-C6Alkyl radical, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, wherein C in the two preceding groups3-C7-cycloalkyl is unsubstituted or partially or fully halogenated; c1-C6-haloalkyl group, C1-C6-alkoxy, C2-C6-alkenyl, C1-C4-alkyl-C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4Alkyl radical, C1-C4alkyl-S (O)n-C1-C4Alkyl radical, C1-C4-alkylamino-C1-C4Alkyl radical, C1-C4-dialkylamino-C1-C4Alkyl radical, C1-C6Cyanoalkyl, phenyl, benzyl, heterocyclyl and heterocyclylmethyl, wherein heterocyclyl in the last two mentioned radicals is a 5-or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1,2,3 or 4 heteroatoms from the group consisting of O, N and S as ring members, wherein phenyl, benzyl, heterocyclyl and heterocyclylmethyl are unsubstituted or substituted by 1,2,3 or 4 identical or different and selected from the group consisting of halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-a group substitution of haloalkoxy;
Rb、R1b、R3b、R4bindependently of one another, from C1-C6Alkyl radical, C3-C7-cycloalkyl, C1-C6-haloalkyl group, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, phenyl and heterocyclyl, wherein heterocyclyl is a 5-or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1,2,3 or 4 heteroatoms from the group consisting of O, N and S as ring members, wherein phenyl and heterocyclyl are unsubstituted or are identical or different by 1,2,3 or 4 and are selected from the group consisting of halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-a group substitution of haloalkoxy;
R3c、R4cindependently of one another, from hydrogen, C1-C6Alkyl radical, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, wherein C in the two preceding groups3-C7-cycloalkyl is unsubstituted or partially or fully halogenated; c1-C6-haloalkyl group, C1-C6-alkoxy, C2-C6-alkenyl, C1-C4-alkyl-C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4Alkyl radical, C1-C4alkyl-S (O)n-C1-C4Alkyl radical, C1-C4-alkylamino-C1-C4Alkyl radical, C1-C4-dialkylamino-C1-C4Alkyl radical, C1-C6Cyanoalkyl, phenyl, benzyl and heterocyclyl, wherein heterocyclyl is a 5-or 6-membered monocyclic saturated moietyUnsaturated or aromatic heterocycles containing 1,2,3 or 4 heteroatoms selected from O, N and S as ring members, where the phenyl, benzyl and heterocyclyl radicals are unsubstituted or are identical or different by 1,2,3 or 4 atoms selected from halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-a group substitution of haloalkoxy;
R3d、R4dindependently of one another, from hydrogen, C1-C6Alkyl radical, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, wherein C in the two preceding groups3-C7-cycloalkyl is unsubstituted or partially or fully halogenated; c1-C6-haloalkyl group, C1-C6-alkoxy, C2-C6-alkenyl, C1-C4-alkyl-C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4Alkyl radical, C1-C4alkyl-S (O)n-C1-C4Alkyl radical, C1-C4-alkylamino-C1-C4Alkyl radical, C1-C4-dialkylamino-C1-C4Alkyl radical, C1-C6-cyanoalkyl, phenyl and benzyl, wherein phenyl and benzyl are unsubstituted or are identical or different by 1,2,3 or 4 and are selected from halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-a group substitution of haloalkoxy;
R3e、R3f、R4e、R4findependently of one another, from hydrogen, C1-C6Alkyl radical, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, wherein C in the two preceding groups3-C7-cycloalkyl is unsubstituted or partially or fully halogenated; c1-C6-haloalkyl group, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl and benzyl, wherein phenyl and benzyl are unsubstituted or are identical or different by 1,2,3 or 4 and are selected from halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-a group substitution of haloalkoxy; or
R3eAnd R3fOr R4eAnd R4fTogether with the nitrogen atom to which they are attached, may form a 4-, 5-, 6-or 7-membered saturated or unsaturated heterocyclic group which may contain as ring members a further heteroatom selected from O, S and N, and which is unsubstituted or carries 1,2,3 or 4 identical or different and selected from ═ O, halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-a group of haloalkoxy groups;
R3g、R4gindependently of one another, from hydrogen, C1-C6Alkyl radical, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, wherein C in the two preceding groups3-C7-cycloalkyl is unsubstituted or partially or fully halogenated; c1-C6-haloalkyl group, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4Alkyl radical, C1-C4-alkylsulfonyl, C1-C4-alkylcarbonyl, phenyl and benzyl, wherein phenyl and benzyl are unsubstituted or are identical or different by 1,2,3 or 4 and are selected from halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-a group substitution of haloalkoxy;
R3h、R4hindependently of one another, from hydrogen, C1-C6Alkyl radical, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, wherein C in the two preceding groups3-C7-cycloalkyl is unsubstituted or partially or fully halogenated; c1-C6-haloalkyl group, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4Alkyl radical, C1-C4-alkylsulfonyl, C1-C4Alkylcarbonyl, the radical C (O) RkPhenyl and benzyl, wherein phenyl and benzyl are unsubstituted or are identical or different by 1,2,3 or 4 and are selected from halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-a group substitution of haloalkoxy; or
R3gAnd R3hOr R4gAnd R4hTogether with the nitrogen atom to which they are attached, may form a 4-, 5-, 6-or 7-membered saturated or partially unsaturated heterocyclyl group which may contain as ring members a further heteroatom selected from O, S and N and which is unsubstituted or carries 1,2,3 or 4 identical or different and selected from ═ O, halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-a group of haloalkoxy groups;
R22selected from hydrogen, C1-C6Alkyl radical, C1-C6-haloalkyl group, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkanesBase, C3-C6-cycloalkenyl radical, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C6Alkyl radical, C1-C6-alkoxy-C1-C6Alkyl radical, C3-C6-cycloalkyl-C1-C6-alkoxy-C1-C6-alkyl, phenyl-Z1phenyl-O-C1-C6Alkyl, phenyl-N (R)23)-C1-C6Alkyl, phenyl-S (O)n-C1-C6-alkyl, heterocyclyl-Z1heterocyclyl-N (R)23)-C1-C6-alkyl, heterocyclyl-O-C1-C6Alkyl and heterocyclyl-S (O)n-C1-C6-alkyl, wherein heterocyclyl is a 5-or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1,2,3 or 4 heteroatoms selected from O, N and S as ring members, wherein phenyl and heterocyclyl are unsubstituted or are identical or different by 1,2,3 or 4 and are selected from cyano, halogen, nitro, thiocyanato, C1-C6Alkyl radical, C1-C6-haloalkyl group, C3-C6Cycloalkyl, C (O) OR23、C(O)N(R23)2、OR23、N(R23)2、S(O)nR24、S(O)2OR23、S(O)2N(R23)2And R23O-C1-C6-alkyl, wherein the heterocyclyl carries 0, 1 or 2 oxo groups;
R23selected from hydrogen, C1-C6Alkyl radical, C1-C6-haloalkyl group, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl and phenyl;
R24is selected from C1-C6Alkyl radical, C1-C6-haloalkyl group, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl and phenyl;
R25is selected from C1-C6Alkyl radical, C1-C6-haloalkyl group, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl radical, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C6Alkyl radical, C1-C6-alkoxy-C1-C6Alkyl radical, C3-C6-cycloalkyl-C1-C6-alkoxy-C1-C6-alkyl, phenyl-Z1phenyl-O-C1-C6Alkyl, phenyl-N (R)23)-C1-C6Alkyl, phenyl-S (O)n-C1-C6-alkyl, heterocyclyl-Z1heterocyclyl-N (R)23)-C1-C6-alkyl, heterocyclyl-O-C1-C6Alkyl and heterocyclyl-S (O)n-C1-C6-alkyl, wherein heterocyclyl is a 5-or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1,2,3 or 4 heteroatoms selected from O, N and S as ring members, wherein phenyl and heterocyclyl are unsubstituted or are identical or different by 1,2,3 or 4 and are selected from cyano, halogen, nitro, thiocyanato, C1-C6Alkyl radical, C1-C6-haloalkyl group, C3-C6Cycloalkyl, C (O) OR23、C(O)N(R23)2、OR23、N(R23)2、S(O)nR24、S(O)2OR23、S(O)2N(R23)2And R23O-C1-C6-alkyl, wherein the heterocyclyl carries 0, 1 or 2 oxo groups;
x is a covalent bond, O, S (O)nOr NR, wherein R is hydrogen or C1-C4-an alkyl group;
k is 0, 1 or 2;
n is 0, 1 or 2;
p is 0, 1 or 2; and is
RkHaving R3cThe meaning of (a).
2. The compound of claim 1, wherein Q is Q1。
3. The compound of claim 1, wherein Q is Q2。
4. The compound of claim 1, wherein Q is Q4。
5. A compound according to any one of the preceding claims wherein R is1Selected from halogen, nitro, cyano, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkoxy-Z1-and R1b-S(O)k-Z1-。
6. The compound of claim 5, wherein R1Selected from halogen, C1-C4-alkyl and C1-C4-alkoxy groups.
7. A compound according to any preceding claim, wherein
R2aSelected from hydrogen, C1-C6Alkyl radical, C1-C6-alkoxy, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4Alkyl radical, C1-C6Haloalkyl, phenyl, benzyl and heterocyclyl, wherein heterocyclyl is a 5-or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1,2,3 or 4 heteroatoms selected from O, N and S as ring members, wherein phenyl, benzyl and heterocyclyl are unsubstituted or are identical or different by 1,2,3 or 4 and are selected from halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-a group substitution of haloalkoxy; and is
R2bSelected from hydrogen, C1-C6Alkyl radical, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4Alkyl radical, C1-C6Haloalkyl, phenyl, benzyl and heterocyclyl, wherein heterocyclyl is a 5-or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1,2,3 or 4 heteroatoms selected from O, N and S as ring members, wherein phenyl, benzyl and heterocyclyl are unsubstituted or are identical or different by 1,2,3 or 4 and are selected from halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-haloalkoxy group.
8. The compound of any one of claims 1 to 6, wherein R2aAnd R2bTogether with the nitrogen atom to which they are attached, form a 4-, 5-, 6-or 7-membered saturated or unsaturated heterocyclyl radical which may contain as ring members a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1,2,3 or 4 identical or different and selected from ═ O, OH, halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-a group of haloalkoxy groups.
9. A compound according to any preceding claim, wherein
R2aIs selected from C1-C6Alkyl radical, C3-C6-cycloalkyl, C1-C4Haloalkyl and phenyl, wherein phenyl is unsubstituted or substituted by 1,2,3 or 4 identical or different C1-C4-alkyl substitution; and is
R2bSelected from hydrogen, C1-C4-alkyl and C3-C6-RingAn alkyl group; or
R2aAnd R2bTogether with the nitrogen atom to which they are bound, form a 5-or 6-membered saturated heterocyclic group which may contain as ring members a further heteroatom selected from O, S and N and which is unsubstituted or carries 1,2,3 or 4 atoms selected from C1-C4Alkyl and fluoro C1-C4-radical R of an alkyl radical2d。
10. A compound according to any one of the preceding claims wherein R is2cIs hydrogen or C1-C4Alkyl, in particular hydrogen.
11. A compound according to any one of the preceding claims having one or more of the following characteristics i) to v)
i)R3Selected from halogen, nitro, C1-C6Alkyl radical, C1-C8-haloalkyl group, C1-C8-haloalkoxy-Z3And R3b-S(O)k-Z3；
ii)R4Is hydrogen or halogen;
iii)R5is hydrogen or halogen;
iv)R6a、R6b、R6c、R6dindependently of one another, from C1-C6Alkyl radical, C1-C4-alkoxy-C1-C4-alkyl and phenyl;
v)R7is hydrogen.
12. A compound according to any one of the preceding claims wherein R is3Is a halogen.
13. A compound according to any one of the preceding claims wherein R is4Is hydrogen.
14. A compound according to any one of the preceding claims wherein R is5Is hydrogen or fluorine.
15. Front sideA compound according to any one of the preceding claims, R6a、R6b、R6c、R6dIndependently of one another is C1-C4-an alkyl group.
16. A compound according to any one of the preceding claims wherein R is7Is hydrogen.
17. A compound according to any one of the preceding claims wherein Z is2Is a covalent bond.
18. A compound according to any one of the preceding claims selected from compounds of formulae i.a ', I.B' and i.d
N-oxides and agriculturally acceptable salts thereof.
19. The compound of claim 18, wherein
R1Is halogen, C1-C2-alkyl or C1-C2-an alkoxy group;
R2ais selected from C1-C4Alkyl radical, C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkyl-methyl, fluoro C1-C4-alkyl, phenyl and benzyl, wherein phenyl and benzyl are unsubstituted or substituted with 1,2,3 or 4 groups selected from halogen, methyl and methoxy;
R2bselected from hydrogen, C1-C4Alkyl radical, C3-C6-cycloalkyl, C3-C6-cycloalkyl-methyl and fluoro C1-C4-an alkyl group; or
R2aAnd R2bTogether with the nitrogen atom to which they are bound form a 5-or 6-membered saturated heterocyclyl group selected from 4-morpholinyl, 4-thiomorpholinyl, 1-piperidinyl and 1-pyrrolidinyl, wherein 4-morpholinyl, 4-thiomorpholinyl, 1-piperidinyl and1-pyrrolidinyl is unsubstituted or has 1,2,3 or 4 substituents selected from C1-C4Alkyl and fluoro C1-C4-radical R of an alkyl radical2d；
R2cSelected from hydrogen and C1-C4-an alkyl group;
R3selected from halogen, C1-C2-alkyl, fluoro C1-C2Alkyl, S-C1-C2Alkyl, S (O) -C1-C2Alkyl, S (O)2-C1-C2Alkyl, S- (fluoro C)1-C2-alkyl), S (O) - (fluoro-C)1-C2Alkyl) and S (O)2- (fluoro C)1-C2-an alkyl group);
R4is a hydrogen atom, and is,
R5is hydrogen or fluorine; and is
R6a、R6bAnd R6dIndependently of one another select C1-C4-alkyl and C1-C4-alkoxy-C1-C4-an alkyl group;
and wherein in particular
R1Is halogen, C1-C2-alkyl or C1-C2-an alkoxy group;
R2ais selected from C1-C4Alkyl radical, C3-C6-cycloalkyl, fluoro C1-C4-alkyl and phenyl, said phenyl being unsubstituted or substituted with 1,2,3 or 4 methyl groups;
R2bselected from hydrogen, C1-C4-alkyl and C3-C6-a cycloalkyl group; or
R2aAnd R2bTogether with the nitrogen atom to which they are attached form a 4-morpholinyl ring;
R2cis hydrogen;
R3is halogen;
R4is a hydrogen atom, and is,
R5is hydrogen or fluorine; and is
R6a、R6bAnd R6dIndependently of one another is C1-C4-an alkyl group.
20. A composition comprising at least one compound as claimed in any of claims 1 to 19, an N-oxide or an agriculturally acceptable salt thereof and at least one auxiliary customary for formulating crop protection compounds.
21. Use of a compound as claimed in any one of claims 1 to 19 or a composition of claim 20 for controlling undesirable vegetation.
22. A method for controlling undesired vegetation, which comprises allowing a herbicidally effective amount of at least one compound as claimed in any of claims 1 to 19 or a composition of claim 20 to act on plants, their seeds and/or their habitat.
The compounds of the prior art often have the problem of insufficient herbicidal activity, especially at low application rates, and/or unsatisfactory selectivity, resulting in low compatibility with crops.
It was therefore an object of the present invention to provide further benzamide compounds which have a strong herbicidal activity, especially even at low application rates, sufficiently low toxicity to humans and animals and/or high compatibility with crops. These benzamide compounds should also show a broad spectrum of activity against a large number of different undesirable plants.
These and other objects are achieved by the compounds of formula I, their N-oxides and their agriculturally useful salts, as defined below.
Accordingly, a first aspect of the present invention relates to compounds of formula I,
wherein
Q is selected from the formula Q1、Q2、Q3And Q4A group of (a);
wherein the formula Q1、Q2、Q3And Q4# in (a) represents the point of attachment to the nitrogen atom;
R1selected from cyano, halogen, nitro, C1-C8Alkyl radical, C2-C8-alkenyl, C2-C8-alkynyl, C1-C8-haloalkyl group, C1-C4-alkoxy-C1-C4Alkyl radical, C1-C4-haloalkoxy-C1-C4Alkyl radical, C1-C8-alkoxy, C1-C4-alkoxy-C1-C4-alkoxy-Z1-、C1-C6-haloalkoxy, R1b-S(O)k-Z1-；
R2aSelected from hydrogen, C1-C6Alkyl radical, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkylamino, di-C1-C6-alkylamino radical, C3-C10-cycloalkyl and C3-C10-cycloalkyl-C1-C4Alkyl, in which the alkyl, alkoxy, alkenyl, alkynyl and cycloalkyl moieties of the aforementioned eight groups are unsubstituted, partially or fully halogenated, or substituted by 1 or 2 radicals R2fSubstituted and wherein the cycloalkyl moieties may also be fused to a benzene ring which is unsubstituted or substituted by 1,2,3 or 4 identical or different radicals R21The substitution is carried out by the following steps,
R2amay also be selected from phenyl and heterocyclyl, where heterocyclyl is a 5-or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1,2,3 or 4 heteroatoms selected from O, N and S as ring members, where phenyl and heterocyclyl are unsubstituted or substituted by 1,2,3 or 4 identical or different radicals R21Substitution;
R2bselected from hydrogen, C1-C6Alkyl radical, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, wherein the alkyl, alkenyl, alkynyl and cycloalkyl moieties of the five aforementioned groups are unsubstituted, partially or fully halogenated, or substituted by 1 or 2 groups R2fSubstitution;
R2bmay also be selected from phenyl and heterocyclyl, where heterocyclyl is a 5-or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1,2,3 or 4 heteroatoms selected from O, N and S as ring members, where phenyl and heterocyclyl are unsubstituted or substituted by 1,2,3 or 4 identical or different radicals R21Substitution; or
R2aAnd R2bTogether with the nitrogen atom to which they are attached may form a 4-, 5-, 6-, 7-or 8-membered saturated or partially unsaturated heterocyclyl group, which may contain as ring members a further heteroatom selected from O, S and N, and whereinSaid heterocyclic radical being unsubstituted or carrying 1,2,3 or 4 radicals R2dOr with 1 radical R2eAnd 0,1, 2 or 3 radicals R2d；
R2cSelected from hydrogen, C1-C6Alkyl radical, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkylamino, di-C1-C6-alkylamino radical, C3-C10-cycloalkyl and C3-C10-cycloalkyl-C1-C4-alkyl, wherein the alkyl, alkenyl, alkynyl and cycloalkyl moieties of the aforementioned seven groups are unsubstituted, partially or fully halogenated, or substituted by 1 or 2 groups R2fSubstituted and wherein the cycloalkyl moieties may also be fused to a benzene ring which is unsubstituted or substituted by 1,2,3 or 4 identical or different radicals R21The substitution is carried out by the following steps,
R2cmay also be selected from phenyl and heterocyclyl, where heterocyclyl is a 5-or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1,2,3 or 4 heteroatoms selected from O, N and S as ring members, where phenyl and heterocyclyl are unsubstituted or substituted by 1,2,3 or 4 identical or different radicals R21Substitution;
R2dare identical or different and are selected from halogen, CN, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4Haloalkoxy, or two radicals R attached to adjacent carbon atoms2dMay together form a fused-on benzene ring which is unsubstituted or substituted by 1,2,3 or 4 identical or different radicals R21Substitution;
R2eis selected from ═ O, OH and R4b-S(O)k-Z4-、R4c-C(O)-Z4-、R4dO-C(O)-Z4-、R4eR4fN-C(O)-Z4-、R4gR4hN-Z4-and R4eR4fNS(O)2-Z4-；
R2fSelected from OH and CN、NH2SH, SCN, nitro, tri (C)1-C4Alkyl) silyl group, C1-C4-alkoxy, C1-C4-haloalkoxy, R3eR3fN-、R3c-C(O)-、HO-C(O)-R3dO-C(O)-、R3dS-C(O)-、R3eR3fN-C(O)-、R3eR3fN-NR3h-C(O)-、R3c-C(S)-、R3dO-C(S)-、R3dS-C(S)-、R3eR3fN-C(S)、R3c-S(O)n-、R3c-S(O)2-O-、R3dO-S(O)2-、R3eR3fNS(O)2-、R3c-C(O)-NR3g-、R3dO-C(O)-NR3g-、R3eR3fN-C(O)-NR3g-、R3eR3fN-NR3h-C(O)-NR3g-、R3dO-S(O)2-NR3g-、R3eR3fNS(O)2-NR3g-、R3c-C(O)-NR3g-C(O)-、R3dO-C(O)-NR3g-C(O)-、R3eR3fN-C(O)-NR3g-C(O)-、R3dO-S(O)2-NR3g-C(O)-、R3eR3fNS(O)2-NR3g-C(O)-、R3c-C(O)-NR3g-S(O)2-、R3dO-C(O)-NR3g-S(O)2-、R3eR3fN-C(O)-NR3g-S(O)2-、(OH)2P(O)-、(C1-C4-alkoxy groups)2P(O)-、R3dO-N ═ CH-, phenyl-X and heterocyclyl-X, where heterocyclyl in the last two mentioned groups is a 5-or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1,2,3 or 4 heteroatoms selected from O, N and S as ring members, where phenyl and heterocyclyl are unsubstituted or are substituted by 1,2,3 or 4 identical or different groups R11Substitution;
R3selected from hydrogen, cyano, thiocyanato, halogen, nitro, hydroxy-Z3-、C1-C6Alkyl radical, C2-C8-alkenyl, C2-C8-alkynyl, C3-C10-cycloalkyl-Z3-、C3-C6-cycloalkenyl-Z3-、C3-C10-cycloalkoxy-Z3-、C3-C10-cycloalkyl-C1-C2-alkoxy, wherein the cyclic groups of the four above groups are unsubstituted or partially or fully halogenated; c1-C4Cyanoalkyl, C1-C8-haloalkyl group, C2-C8-haloalkenyl, C3-C8-haloalkynyl, C1-C8-alkoxy-Z3-、C1-C8-haloalkoxy-Z3-、C1-C4-alkoxy-C1-C4-alkoxy-Z3-、C1-C4-haloalkoxy-C1-C4-alkoxy-Z3-、C2-C8-alkenyloxy-Z3-、C2-C8-alkynyloxy-Z3-、C2-C8-haloalkenyloxy-Z3-、C3-C8-haloalkynyloxy-Z3-、R3b-S(O)k-Z3-、R3c-C(O)-Z3-、R3dO-C(O)-Z3-、R3dO-N＝CH-Z3-、R3eR3fN-C(O)-Z3-、R3gR3hN-Z3-、R22C(O)O-Z3-、R25OC(O)O-Z3-、(R22)2NC(O)O-Z3-、R25S(O)2O-Z3-、R22OS(O)2-Z3-、(R22)2NS(O)2-Z3-、R25OC(O)N(R22)-Z3-、(R22)2NC(O)N(R22)-Z3-、(R22)2NS(O)2N(R22)-Z3-、(OH)2P(O)-Z3-、(C1-C4-alkoxy groups)2P(O)-Z3-, phenyl-Z3a-and heterocyclyl-Z3a-, wherein the heterocyclic group is 3-, 4-, 5-or 6-memberedMonocyclic or 8-, 9-or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle which contains 1,2,3 or 4 heteroatoms selected from O, N and S as ring members, wherein phenyl-Z3a-and heterocyclyl-Z3aThe cyclic groups in (A) are unsubstituted or substituted by 1,2,3 or 4 identical or different radicals R21Substitution;
R4selected from hydrogen, halogen, cyano-Z1、C1-C8Alkyl, nitro, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, wherein C in the two preceding groups3-C7-cycloalkyl is unsubstituted or partially or fully halogenated; c2-C8-alkenyl, C2-C8-alkynyl, C1-C8-haloalkyl group, C1-C3-alkylamino radical, C1-C3-dialkylamino radical, C1-C3-alkylamino-S (O)k、C1-C3-alkylcarbonyl group, C1-C8-alkoxy, C1-C4-alkoxy-C1-C4Alkyl radical, C1-C4-alkoxy-C1-C4-alkoxy-Z1-、C1-C4-alkylthio-C1-C4-alkylthio-Z1-、C2-C6Alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy, C1-C4-haloalkoxy-C1-C4Alkyl radical, C1-C4-haloalkoxy-C1-C4-alkoxy-Z1-、R1b-S(O)k-Z1-, phenoxy-Z1And heterocyclyloxy-Z1-, wherein heterocyclyloxy is an oxygen-bonded 5-or 6-membered monocyclic or 8-, 9-or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle which contains 1,2,3 or 4 heteroatoms from the group consisting of O, N and S as ring members, wherein the cyclic groups in phenoxy and heterocyclyloxy are unsubstituted or substituted by 1,2,3 or 4 identical or different radicals R11Substitution;
R5selected from hydrogen, halogen, cyano-Z1-, nitro, C1-C8Alkyl radical, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, wherein C in the two preceding groups3-C7-cycloalkyl is unsubstituted or partially or fully halogenated; c2-C8-alkenyl, C2-C8-alkynyl, C1-C8-haloalkyl group, C1-C3-alkylamino radical, C1-C3-dialkylamino radical, C1-C3-alkylamino-S (O)k、C1-C3-alkylcarbonyl group, C1-C8-alkoxy, C1-C4-alkoxy-C1-C4Alkyl radical, C1-C4-alkoxy-C1-C4-alkoxy-Z1-、C1-C4-alkylthio-C1-C4Alkyl radical, C1-C4-alkylthio-C1-C4-alkylthio-Z1-、C2-C6Alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy, C1-C4-haloalkoxy-C1-C4Alkyl radical, C1-C4-haloalkoxy-C1-C4-alkoxy-Z1-、R1b-S(O)k-Z1-, phenoxy-Z1And heterocyclyloxy-Z1-, wherein heterocyclyloxy is a 5-or 6-membered monocyclic or 8-, 9-or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle which is linked via an oxygen atom and contains 1,2,3 or 4 heteroatoms from the group O, N and S as ring members, wherein the cyclic radicals phenoxy and heterocyclyloxy are unsubstituted or substituted by 1,2,3 or 4 identical or different radicals R11Substitution;
R6a、R6b、R6c、R6dindependently of one another select C1-C6Alkyl radical, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, wherein C of the two preceding groups3-C7-cycloalkyl is unsubstituted or partially or fully halogenated; c1-C6-haloalkyl group, C2-C6-alkenyl, C2-C6-alkynyl, C2-C6-haloalkenyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4Alkyl radical, C1-C4-haloalkoxy-C1-C4-alkyl, Rb-S(O)n-C1-C3-alkyl, phenyl and benzyl, wherein phenyl and benzyl are unsubstituted or substituted by 1,2,3 or 4, the same or different, groups selected from halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-a group substitution of haloalkoxy;
R7selected from hydrogen, CN, NH2、C1-C6Alkyl radical, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, wherein C of the two preceding groups3-C7-cycloalkyl is unsubstituted or partially or fully halogenated; c1-C6-haloalkyl group, C2-C6-alkenyl, C2-C6-alkynyl, C2-C6-haloalkenyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4Alkyl radical, C1-C4-haloalkoxy-C1-C4Alkyl radical, C1-C4-cyanoalkyl, R3b-S(O)k-Z3b-、R3c-C(O)-Z3b-、R3dO-C(O)-Z3b-、R3dO-N＝CH-Z3b-、R3eR3fN-C(O)-Z3b-、R3gR3hN-Z3b-、R22C(O)O-Z3b-、R25OC(O)O-Z3b-、(R22)2NC(O)O-Z3b-、R25S(O)2O-Z3b-、R22OS(O)2-Z3b-、(R22)2NS(O)2-Z3b-、R25OC(O)N(R22)-Z3b-、(R22)2NC(O)N(R22)-Z3b-、(R22)2NS(O)2N(R22)-Z3b-、(OH)2P(O)-Z3b-、(C1-C4-alkoxy groups)2P(O)-Z3b-, phenyl-Z3a-and heterocyclyl-Z3a-, wherein heterocyclyl is a 3-, 4-, 5-or 6-membered monocyclic or 8-, 9-or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle which contains 1,2,3 or 4 heteroatoms from the group consisting of O, N and S as ring members, wherein phenyl-Z is phenyl3a-and heterocyclyl-Z3aThe cyclic groups in (A) are unsubstituted or substituted by 1,2,3 or 4 identical or different radicals R21Substitution;
R11、R21independently of one another, from cyano, OH, halogen, nitro, C1-C6Alkyl radical, C3-C7-cycloalkyl, C3-C7-halocycloalkyl, C1-C6-haloalkyl group, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C6-alkoxy, C1-C4-alkoxy-C1-C4Alkyl radical, C1-C4-alkylthio-C1-C4Alkyl radical, C1-C4-haloalkoxy-C1-C4Alkyl radical, C1-C4-alkoxy-C1-C4-alkoxy, C3-C7Cycloalkoxy and C1-C6Haloalkoxy, or two radicals R each bound to the same carbon atom11Or R21May together form a group ═ O, or two R groups each bound to an adjacent carbon atom11Or R21May together form a radical selected from C3-C5Alkylene, O-C2-C4Alkylene and O- (C)1-C3-alkylene) -O-;
Z1、Z3、Z4independently of one another, from covalent bonds and unsubstituted or partially or completely fluorinated C1-C4-an alkanediyl group;
Z2is a covalent bond or is selected from C1-C4Alkanediyl and C1-C4-alkanediyl-O-C1-C4-a divalent radical of an alkanediyl radical,
wherein in the last two mentioned radicals, C1-C4-alkanediyl is linear, and wherein C1-C4Alkanediyl unsubstituted or partially or completely fluorinated or substituted by 1,2,3 or 4 radicals RzSubstitution;
Z3aselected from covalent bond, C1-C4Alkanediyl, O-C1-C4Alkanediyl, C1-C4alkanediyl-O and C1-C4-alkanediyl-O-C1-C4-an alkanediyl group;
Z3bis selected from C1-C4Alkanediyl, C1-C4alkanediyl-O and C1-C4-alkanediyl-O-C1-C4-an alkanediyl group;
Rzare identical or different and are selected from C1-C6Alkyl radical, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, wherein C in the two preceding groups3-C7-cycloalkyl is unsubstituted or partially or fully halogenated; c1-C6-haloalkyl group, C1-C6-alkoxy, C2-C6-alkenyl, C1-C4-alkyl-C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4Alkyl radical, C1-C4alkyl-S (O)n-C1-C4Alkyl radical, C1-C4-alkylamino-C1-C4Alkyl radical, C1-C4-dialkylamino-C1-C4Alkyl radical, C1-C6Cyanoalkyl, phenyl, benzyl, heterocyclyl and heterocyclylmethyl, wherein heterocyclyl in the last two mentioned radicals is a 5-or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1,2,3 or 4 heteroatoms from the group consisting of O, N and S as ring members, wherein phenyl, benzyl, heterocyclyl and heterocyclylmethyl are unsubstituted or substituted by 1,2,3 or 4 identical or different and selected from the group consisting of halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-a group substitution of haloalkoxy;
Rb、R1b、R3b、R4bindependently of one another, from C1-C6Alkyl radical, C3-C7-cycloalkyl, C1-C6-haloalkyl group, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, phenyl and heterocyclyl, wherein heterocyclyl is a 5-or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1,2,3 or 4 heteroatoms from the group consisting of O, N and S as ring members, wherein phenyl and heterocyclyl are unsubstituted or are identical or different by 1,2,3 or 4 and are selected from the group consisting of halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-a group substitution of haloalkoxy;
R3c、R4cindependently of one another, from hydrogen, C1-C6Alkyl radical, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, wherein C in the two preceding groups3-C7-cycloalkyl is unsubstituted or partially or fully halogenated; c1-C6-haloalkyl group, C1-C6-alkoxy, C2-C6-an alkenyl group,C1-C4-alkyl-C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4Alkyl radical, C1-C4alkyl-S (O)n-C1-C4Alkyl radical, C1-C4-alkylamino-C1-C4Alkyl radical, C1-C4-dialkylamino-C1-C4Alkyl radical, C1-C6Cyanoalkyl, phenyl, benzyl and heterocyclyl, where heterocyclyl is a 5-or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1,2,3 or 4 heteroatoms selected from O, N and S as ring members, where phenyl, benzyl and heterocyclyl are unsubstituted or are identical or different by 1,2,3 or 4 and are selected from halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-a group substitution of haloalkoxy;
R3d、R4dindependently of one another, from hydrogen, C1-C6Alkyl radical, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, wherein C in the two preceding groups3-C7-cycloalkyl is unsubstituted or partially or fully halogenated; c1-C6-haloalkyl group, C1-C6-alkoxy, C2-C6-alkenyl, C1-C4-alkyl-C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4Alkyl radical, C1-C4alkyl-S (O)n-C1-C4Alkyl radical, C1-C4-alkylamino-C1-C4Alkyl radical, C1-C4-dialkylamino-C1-C4Alkyl radical, C1-C6-cyanoalkyl, phenyl and benzyl, wherein phenyl and benzyl are unsubstituted or are identical or different by 1,2,3 or 4 and are selected from halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-a group substitution of haloalkoxy;
R3e、R3f、R4e、R4findependently of one another, from hydrogen, C1-C6Alkyl radical, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, wherein C in the two preceding groups3-C7-cycloalkyl is unsubstituted or partially or fully halogenated; c1-C6-haloalkyl group, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl and benzyl, wherein phenyl and benzyl are unsubstituted or are identical or different by 1,2,3 or 4 and are selected from halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-a group substitution of haloalkoxy; or
R3eAnd R3fOr R4eAnd R4fTogether with the nitrogen atom to which they are attached, may form a 4-, 5-, 6-or 7-membered saturated or unsaturated heterocyclyl group which may contain as ring members a further heteroatom selected from O, S and N, and which is unsubstituted or carries 1,2,3 or 4 identical or different and selected from ═ O, halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-a group of haloalkoxy groups;
R3g、R4gindependently of one another, from hydrogen, C1-C6Alkyl radical, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkanesWherein C in the two preceding groups3-C7-cycloalkyl is unsubstituted or partially or fully halogenated; c1-C6-haloalkyl group, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4Alkyl radical, C1-C4-alkylsulfonyl, C1-C4-alkylcarbonyl, phenyl and benzyl, wherein phenyl and benzyl are unsubstituted or are identical or different by 1,2,3 or 4 and are selected from halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-a group substitution of haloalkoxy;
R3h、R4hindependently of one another, from hydrogen, C1-C6Alkyl radical, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, wherein C in the two preceding groups3-C7-cycloalkyl is unsubstituted or partially or fully halogenated; c1-C6-haloalkyl group, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4Alkyl radical, C1-C4-alkylsulfonyl, C1-C4Alkylcarbonyl, the radical C (O) RkPhenyl and benzyl, wherein phenyl and benzyl are unsubstituted or are identical or different by 1,2,3 or 4 and are selected from halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-a group substitution of haloalkoxy; or
R3gAnd R3hOr R4gAnd R4hTogether with the nitrogen atom to which they are attached may form a 4-, 5-, 6-or 7-membered saturated or partially unsaturated heterocyclyl group, which isMay contain as ring members a further heteroatom selected from O, S and N, unsubstituted or carrying 1,2,3 or 4 identical or different and selected from ═ O, halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-a group of haloalkoxy groups;
R22selected from hydrogen, C1-C6Alkyl radical, C1-C6-haloalkyl group, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl radical, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C6Alkyl radical, C1-C6-alkoxy-C1-C6Alkyl radical, C3-C6-cycloalkyl-C1-C6-alkoxy-C1-C6-alkyl, phenyl-Z1phenyl-O-C1-C6Alkyl, phenyl-N (R)23)-C1-C6Alkyl, phenyl-S (O)n-C1-C6-alkyl, heterocyclyl-Z1heterocyclyl-N (R)23)-C1-C6-alkyl, heterocyclyl-O-C1-C6Alkyl and heterocyclyl-S (O)n-C1-C6-alkyl, wherein heterocyclyl is a 5-or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1,2,3 or 4 heteroatoms selected from O, N and S as ring members, wherein phenyl and heterocyclyl are unsubstituted or are identical or different by 1,2,3 or 4 and are selected from cyano, halogen, nitro, thiocyanato, C1-C6Alkyl radical, C1-C6-haloalkyl group, C3-C6Cycloalkyl, C (O) OR23、C(O)N(R23)2、OR23、N(R23)2、S(O)nR24、S(O)2OR23、S(O)2N(R23)2And R23O-C1-C6-alkyl, wherein the heterocyclyl carries 0,1 or 2 oxo groups;
R23selected from hydrogen, C1-C6Alkyl radical, C1-C6-haloalkyl group, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl and phenyl;
R24is selected from C1-C6Alkyl radical, C1-C6-haloalkyl group, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl and phenyl;
R25is selected from C1-C6Alkyl radical, C1-C6-haloalkyl group, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl radical, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C6Alkyl radical, C1-C6-alkoxy-C1-C6Alkyl radical, C3-C6-cycloalkyl-C1-C6-alkoxy-C1-C6-alkyl, phenyl-Z1phenyl-O-C1-C6Alkyl, phenyl-N (R)23)-C1-C6Alkyl, phenyl-S (O)n-C1-C6-alkyl, heterocyclyl-Z1heterocyclyl-N (R)23)-C1-C6-alkyl, heterocyclyl-O-C1-C6Alkyl and heterocyclyl-S (O)n-C1-C6-alkyl, wherein heterocyclyl is a 5-or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1,2,3 or 4 heteroatoms selected from O, N and S as ring members, wherein phenyl and heterocyclyl are unsubstituted or substituted by 1,23 or 4 are identical or different and are selected from the group consisting of cyano, halogen, nitro, thiocyanato, C1-C6Alkyl radical, C1-C6-haloalkyl group, C3-C6Cycloalkyl, C (O) OR23、C(O)N(R23)2、OR23、N(R23)2、S(O)nR24、S(O)2OR23、S(O)2N(R23)2And R23O-C1-C6-alkyl, wherein the heterocyclyl carries 0,1 or 2 oxo groups;
x is a covalent bond, O, S (O)nOr NR, wherein R is hydrogen or C1-C4-an alkyl group;
k is 0,1 or 2;
n is 0,1 or 2;
p is 0,1 or 2; and is
RkAnd R3cThe definitions are the same.
The invention also relates to the N-oxides of the compounds of formula I, to the salts, in particular the agriculturally useful salts, of the compounds of formula I, and to the salts of said N-oxides.
The compounds of the invention, i.e. the compounds of the formula I, their N-oxides and their agriculturally useful salts, can be used, inter alia, for controlling undesirable vegetation. The present invention therefore also relates to the use of compounds of the formula I, N-oxides or agriculturally acceptable salts thereof or of compositions comprising at least one compound of the formula I, N-oxides or agriculturally acceptable salts thereof for controlling or controlling undesirable vegetation.
The invention also relates to compositions comprising at least one compound of formula I, an N-oxide or a salt thereof and at least one auxiliary. The present invention relates in particular to agricultural compositions comprising at least one compound of the formula I or an agriculturally useful salt thereof and at least one auxiliary which is customary for crop protection formulations.
The present invention also relates to a method for controlling or controlling undesired plants, which comprises allowing a herbicidally effective amount of at least one compound of the formula I or a salt thereof to act on the undesired plants, their seeds and/or their habitat.
Depending on the nature of the substituents, the compounds of the formula I may have one or more chiral centers, in which case they may be present as enantiomers or diastereoisomers, as well as in the form of pure enantiomers or pure diastereomers. The present invention provides both the pure enantiomers or pure diastereomers of the compounds of formula I and mixtures thereof as well as the inventive use of the pure enantiomers or pure diastereomers of the compounds of formula I or mixtures thereof. Suitable compounds of formula I also include all possible geometric stereoisomers (cis/trans isomers) and mixtures thereof. The cis/trans isomer may exist with respect to an alkene, a carbon-nitrogen double bond, a nitrogen-sulfur double bond, or an amide group. The term "stereoisomer" includes both optical isomers, such as enantiomers or diastereomers, wherein the latter occur due to more than one chiral center in the molecule, as well as geometric isomers (cis/trans isomers).
Furthermore, the present invention relates to compounds as defined herein, wherein one or more of the atoms shown in formula I have been replaced by a stable, preferably non-radioactive isotope thereof (e.g. hydrogen is replaced by deuterium,12C quilt13C is substituted,14N quilt15N is substituted,16O quilt18O substitution), especially wherein at least one hydrogen atom has been replaced by a deuterium atom. Of course, the compounds of the invention contain more of the corresponding isotope than naturally occurring and therefore always present in the compounds of formula I.
The compounds of the invention may be amorphous or may exist in one or more different crystalline states (polymorphs) which may have different macroscopic properties such as stability or show different biological properties such as activity. The present invention includes both amorphous and crystalline compounds of formula I, enantiomers or diastereomers thereof, mixtures of different crystalline states of the corresponding compounds of formula I, enantiomers or diastereomers thereof, and amorphous or crystalline salts thereof.
Salts of the compounds of the present invention are preferably agriculturally acceptable salts. They may be formed in conventional manner, for example by reacting a compound of the invention with an acid if it has a basic functional group, or with a suitable base if it has an acidic functional group.
Useful agriculturally useful salts are in particular those salts of cations or acid addition salts of acids whose cations and anions, respectively, do not have any adverse effect on the herbicidal action of the compounds according to the invention. Suitable cations are especially alkali metal ions, preferably lithium, sodium and potassium ions; alkaline earth metal ions, preferably calcium, magnesium and barium ions; transition metal ions, preferably manganese, copper, zinc and iron ions; also ammonium (NH)4 +) And wherein 1-4 hydrogen atoms are replaced by C1-C4Alkyl radical, C1-C4-hydroxyalkyl, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, hydroxy-C1-C4-alkoxy-C1-C4Alkyl, phenyl or benzyl substituted ammonium. Examples of substituted ammonium ions include methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2- (2-hydroxyethoxy) ethylammonium, di (2-hydroxyethyl) ammonium, benzyltrimethylammonium and benzyl-triethylammonium, and furthermoreIon, sulfonium ion, preferably tris (C)1-C4-alkyl) sulfonium, and sulfoxonium ions, preferably tri (C)1-C4-alkyl) sulfoxonium.
The anions of the useful acid addition salts are predominantly chloride, bromide, fluoride, hydrogen sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, hydrogen carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and C1-C4The anion of an alkanoic acid, preferably formate, acetate, propionate and butyrate. They may be formed by reacting a compound of the invention with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
The term "N-oxide" relates to derivatives of compounds of formula I which carry at least one oxygen atom on the nitrogen atom. For example, the term "N-oxide" may relate to a derivative of a compound of formula ICompound (ii) wherein the group Q1、Q2、Q3Or Q4One imino nitrogen of (a) carries an oxygen atom. In other words, the N-oxides of the compounds I are those in which the nitrogen atom, for example the ring nitrogen atom or the nitrogen atom of an amino group in the group Q, is in oxidized form, i.e. as the group N+-O-present compounds. N-oxides are generally prepared by oxidation of compounds of formula I, for example with hydrogen peroxide or peroxy acids such as m-chloroperoxybenzoic acid (mCPBA), peroxyacetic acid or caro's acid (peroxymonosulfuric acid).
The term "undesirable vegetation" ("weeds") is understood to include any plant that grows in a non-crop area or crop locus or in a sown and other desired crop locus, where the plant is any plant species other than the sown or desired crop (if any), including germinating seeds, emerging seedlings and formed plants thereof. Weeds in the broadest sense are plants that are considered undesirable at a particular location.
The organic moieties mentioned in the above definitions of the variables (like the term halogen) are collective terms for the individual enumeration of the group members. Prefix Cn-CmIn each case representing the possible number of carbon atoms in the radical.
The term "halogen" denotes in each case fluorine, bromine, chlorine or iodine, especially fluorine, chlorine or bromine.
The term "partially or fully halogenated" means that 1 or more, for example 1,2,3,4 or 5 or all hydrogen atoms of a given group are replaced by halogen atoms, in particular fluorine or chlorine. Partially or fully halogenated groups are also referred to hereinafter as "halo groups". For example, partially or fully halogenated alkyl groups are also referred to as haloalkyl groups.
The term "alkyl" as used herein (and in the alkyl portion of other groups containing alkyl, such as alkoxy, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulfonyl and alkoxyalkyl) denotes in each case a radical having typically from 1 to 10 carbon atoms (═ C)1-C10-alkyl) or 1-8 carbon atoms (═ C1-C8-alkyl), often 1-6 carbon atoms (═ C)1-C6-alkyl), in particular 1 to 4 carbon atoms (═ C)1-C4-alkyl) and especially 1 to 3 carbon atoms (═ C)1-C3-alkyl) or 1 or 2 carbon atoms (═ C1-C2-alkyl) straight or branched chain alkyl. C1-C2-alkyl is methyl or ethyl. C1-C3-alkyl is methyl, ethyl, n-propyl or isopropyl. C1-C4Examples of-alkyl are methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl (═ sec-butyl), isobutyl and tert-butyl. C1-C6Examples of-alkyl radicals are other than p-C1-C4-alkyl radicals which are mentioned in addition to n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2, 2-dimethylbutyl, 2, 3-dimethylbutyl, 3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 2-trimethylpropyl, 1,2, 2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl. C1-C8Examples of-alkyl radicals other than p-C1-C6Alkyl radicals which are mentioned are, in addition to those mentioned, n-heptyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 1-ethylpentyl, 2-ethylpentyl, 3-ethylpentyl, n-octyl, 1-methylheptyl, 2-methylheptyl, 1-ethylhexyl, 2-ethylhexyl, 1, 2-dimethylhexyl, 1-propylpentyl and 2-propylpentyl. C1-C10Examples of-alkyl radicals other than p-C1-C8Alkyl radicals are mentioned in addition to nonyl, decyl, 2-propylheptyl and 3-propylheptyl.
The term "haloalkyl" as used herein (and in haloalkyl moieties of other groups containing haloalkyl, such as haloalkoxy, haloalkylthio, haloalkylcarbonyl, haloalkylsulfonyl and haloalkylsulfinyl) is also intended to denote "partially or fully halogenated alkyl" in each case referring to a radical having from 1 to 8 carbon atoms (═ C) as generally defined above1-C8Haloalkyl), often with 1 to 6 carbon atoms (═ C)1-C6Haloalkyl), more often with 1 to 4 carbon atoms (═ C)1-C4-haloalkyl), wherein the hydrogen atoms of the group are partially or completely replaced by halogen atoms. "fluoroalkyl" as used herein (and in the fluoroalkyl moiety of other groups comprising fluoroalkyl, for example fluoroalkoxy) denotes in each case a radical as defined above, generally having from 1 to 8 carbon atoms (═ fluoro C)1-C8-alkyl), often 1 to 6 carbon atoms (═ fluoro C)1-C6-alkyl), more often 1 to 4 carbon atoms (═ fluoro C)1-C4-alkyl), in particular 1 or 2 carbon atoms (═ fluoro C)1-C2-alkyl), wherein the hydrogen atoms of the group are partially or completely replaced by fluorine atoms. Preferred haloalkyl moieties are selected from C1-C4-haloalkyl, more preferably selected from C1-C2Haloalkyl, more preferably from halomethyl, especially from fluoro C1-C2-an alkyl group. Halomethyl is methyl in which 1,2 or 3 hydrogen atoms are replaced by halogen atoms. Examples are bromomethyl, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl and the like. Fluoro C1-C2Examples of-alkyl are fluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2,2 difluoroethyl, 2,2, 2-trifluoroethyl, pentafluoroethyl and the like. C1-C2Examples of-haloalkyl radicals other than p-fluoro C1-C2And in addition to those mentioned for alkyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 2, 2-dichloroethyl, 2,2, 2-trichloroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2, 2-difluoroethyl, 2, 2-dichloro-2-fluoroethyl, 1-bromoethyl and the like. Except for C1-C2-haloalkyl radicals other than those described, C1-C4Examples of haloalkyl are also 1-fluoropropyl, 2-fluoropropyl, 3, 3-difluoropropyl, 3,3, 3-trifluoropropyl, pentafluoropropyl, 1,1-trifluoropropan-2-yl, 3-chloropropyl, 4-chlorobutyl and the like.
The term "cyanoalkyl" as used herein means having 1 to 4 ("C)1-C4Cyanoalkyl) or 1 to 6 ("C)1-C6Cyanoalkyl) linear or branched alkyl of carbon atoms (as described above), in which 1 or 2, preferably 1, hydrogen atom of these groups is replaced by a Cyano (CN) group. Examples are cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 1-cyanopropyl, 2-cyanopropyl, 3-cyanopropyl, 1-cyanobutyl, 2-cyanobutyl, 3-cyanobutyl, 4-cyanobutyl and the like.
The term "cycloalkyl" as used herein (and in cycloalkyl moieties of other groups containing cycloalkyl groups, such as cycloalkoxy and cycloalkylalkyl) denotes in each case, usually, having from 3 to 10 carbon atoms (═ C3-C10-cycloalkyl), preferably 3 to 7 carbon atoms (═ C)3-C7-cycloalkyl) or in particular 3 to 6 carbon atoms (═ C)3-C6-cycloalkyl) groups are selected from the group consisting of monocyclic or bicyclic saturated alicyclic groups. Examples of monocyclic saturated alicyclic groups having 3 to 6 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Examples of monocyclic saturated alicyclic groups having 3 to 7 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl. Examples of monocyclic groups having 3 to 10 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl and cyclodecyl. C5-C6-cycloalkyl is cyclopentyl or cyclohexyl. Examples of the bicyclic group having 6 to 10 carbon atoms include bicyclo [2.1.1]Hexyl, bicyclo [2.2.1]Heptyl, bicyclo [3.1.1]Heptyl, bicyclo [2.2.1]Heptyl, bicyclo [2.2.2]Octyl and bicyclo [3.2.1]And (4) octyl. Preferably, the term cycloalkyl denotes a monocyclic saturated hydrocarbon group. When a cycloalkyl group is fused to a benzene ring, the cycloalkyl ring is monocyclic, and of course forms a bicyclic fused ring system together with the fused benzene ring. Cycloalkyl fused with a benzene ring is preferably C fused with a benzene ring5-C6-a cycloalkyl group. C condensed with benzene rings5-C6Examples of-cycloalkyl are indanyl and tetrahydronaphthyl.
The term "halocycloalkyl" as used herein (and in halocycloalkyl moieties of other groups comprising halocycloalkyl groups, for example halocycloalkylmethyl) denotes in each case a monocyclic or bicyclic cycloaliphatic radical having in general 3 to 10 carbon atoms, preferably 3 to 7 carbon atoms or in particular 3 to 6 carbon atoms, in which at least one, for example 1,2,3,4 or 5, hydrogen atoms are replaced by halogen, in particular fluorine or chlorine. Examples are 1-and 2-fluorocyclopropyl, 1,2-, 2, 2-and 2, 3-difluorocyclopropyl, 1,2, 2-trifluorocyclopropyl, 2,2,3, 3-tetrafluorocyclopropyl, 1-and 2-chlorocyclopropyl, 1,2-, 2, 2-and 2, 3-dichlorocyclopropyl, 1,2, 2-trichlorocyclopropyl, 2,2,3, 3-tetrachlorocyclopropyl, 1-, 2-and 3-fluorocyclopentyl, 1,2-, 2,3-, 3,4-, 2, 5-difluorocyclopentyl, 1-, 2-and 3-chlorocyclopentyl, 1,2-, 2,3-, 3,4-, 2, 5-dichlorocyclopentyl, and the like.
The term "cycloalkyl-alkyl" as used herein denotes a cycloalkyl group as defined above, which is linked to the rest of the molecule through an alkylene group. The term "C3-C7-cycloalkyl-C1-C4-alkyl "means C as defined above3-C7-cycloalkyl through C as defined above1-C4-an alkyl group is attached to the rest of the molecule. The term "C3-C10-cycloalkyl-C1-C4-alkyl "means C as defined above3-C10-cycloalkyl through C as defined above1-C4-an alkyl group is attached to the rest of the molecule. Examples are cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl, cyclobutylpropyl, cyclopentylmethyl, cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl, cyclohexylpropyl, cycloheptylmethyl, cycloheptylethyl, cycloheptylpropyl and the like. The term "C3-C6-cycloalkyl-C1-C6-alkyl "means C as defined above3-C6-cycloalkyl through C as defined above1-C6-an alkyl group is attached to the rest of the molecule. Examples are cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl, cyclobutylpropyl, cyclopentylmethyl, cyclopentylEthyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl, cyclohexylpropyl, and the like. The term "C3-C6-cycloalkyl-methyl "means C as defined above3-C6Cycloalkyl radicals represented by CH2The group is attached to the rest of the molecule. Examples are cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl and cyclohexylmethyl.
The term "cycloalkenyl" as used herein denotes monocyclic partially unsaturated non-aromatic hydrocarbon radicals. C3-C6Examples of cycloalkenyl are cyclopropyl1-en-1-yl, cyclopropyl1-en-3-yl, cyclobut-1-en-1-yl, cyclobut-1-en-3-yl, cyclopent-1-en-1-yl, cyclopent-1-en-3-yl, cyclopent-1-en-4-yl, cyclopent-1, 3-dien-1-yl, cyclopent-1, 3-dien-2-yl, cyclopent-1, 3-dien-5-yl, cyclohex-1-en-1-yl, cyclohex-1-en-3-yl, cyclohex-1-en-4-yl, Cyclohexa-1, 3-dien-1-yl, cyclohexa-1, 3-dien-2-yl, cyclohexa-1, 3-dien-5-yl, cyclohexa-1, 4-dien-1-yl and cyclohexa-1, 4-dien-3-yl.
The term "alkenyl" as used herein denotes in each case in general 2 to 8(═ C)2-C8-alkenyl), preferably 2 to 6 carbon atoms (═ C)2-C6Alkenyl), in particular 2 to 4 carbon atoms (═ C)2-C4Alkenyl) and monounsaturated linear or branched hydrocarbon radicals having a double bond in any position, e.g. C2-C4Alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl or 2-methyl-2-propenyl; c2-C6Alkenyl groups such as vinyl, 1-propenyl, 2-propenyl, 1-methylvinyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 2-methyl-2-butenyl, 1-methyl-2-butenyl, 2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1-dimethyl-2-propenyl1, 2-dimethyl-1-propenyl group, 1, 2-dimethyl-2-propenyl group, 1-ethyl-1-propenyl group, 1-ethyl-2-propenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group, 1-methyl-1-pentenyl group, 2-methyl-1-pentenyl group, 3-methyl-1-pentenyl group, 4-methyl-1-pentenyl group, 1-methyl-2-pentenyl group, 2-methyl-2-pentenyl group, 3-methyl-2-pentenyl group, 4-methyl-2-pentenyl group, 1-methyl-3-pentenyl group, 1-ethyl-1-propenyl group, 1-ethyl-2-hexenyl group, 1-methyl-1-, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1-dimethyl-2-butenyl, 1-dimethyl-3-butenyl, 1, 2-dimethyl-1-butenyl, 1, 2-dimethyl-2-butenyl, 1, 2-dimethyl-3-butenyl, 1, 3-dimethyl-1-butenyl, 1, 3-dimethyl-2-butenyl, 2-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 1-dimethyl-2-butenyl, 2-dimethyl-3-butenyl, 1, 3-dimethyl-3-butenyl, 2-dimethyl-3-butenyl, 2, 3-dimethyl-1-butenyl, 2, 3-dimethyl-2-butenyl, 2, 3-dimethyl-3-butenyl, 3-dimethyl-1-butenyl, 3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1, 2-trimethyl-2-propenyl, 2-ethyl-3-butenyl, 2-methyl-2-propenyl, 2-methyl-2-butenyl, 2-methyl, 1-ethyl-1-methyl-2-propenyl group, 1-ethyl-2-methyl-1-propenyl group, 1-ethyl-2-methyl-2-propenyl group and the like, or C2-C8Alkenyl radicals, e.g. for C2-C6Alkenyl and further 1-heptenyl, 2-heptenyl, 3-heptenyl, 1-octenyl, 2-octenyl, 3-octenyl, 4-octenyl and positional isomers thereof.
C1-C4-alkyl-C2-C6Alkenyl corresponds to C3-C10-an alkenyl group. Examples are those mentioned above, except for the vinyl group.
The term "haloalkenyl" (which may also be referred to as "alkenyl substituted with halogen"), haloalkenyl moiety of haloalkenyloxy, and the like, as used herein, means having 2 to 8(═ C)2-C8-haloalkenyl) or 2-6(═ C)2-C6-haloalkenyl) or 2-4(═ C)2-C4Haloalkenyl) carbon atoms and double bonds in any positionAnd straight-chain or branched hydrocarbon groups in which some or all of the hydrogen atoms in these groups are replaced by the above-mentioned halogen atoms, particularly fluorine, chlorine and bromine, such as chloroethenyl, chloroallyl and the like.
The term "alkynyl" as used herein means having typically 2 to 8(═ C)2-C8-alkynyl), typically 2-6(═ C), and2-C6-alkynyl), preferably 2-4 carbon atoms (═ C)2-C4-alkynyl) and unsaturated linear or branched hydrocarbon radicals having a triple bond in any position, e.g. C2-C4Alkynyl, e.g. ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, etc., C2-C6Alkynyl groups, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1-dimethyl-2-butynyl, 1-dimethyl-3-butynyl, 1, 2-dimethyl-3-butynyl, 2-dimethyl-3-butynyl, 3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 1-methyl-4-pentynyl, 1-methyl-3-pentynyl, 2-methyl-4-pentynyl, 1-dimethyl-2-butynyl, 1-dimethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl, and the like.
The term "haloalkynyl" as used herein, also refers to "alkynyl substituted with halogen" and refers to a compound having typically 3 to 8 carbon atoms (═ C)3-C8-haloalkynyl), often 3-6(═ C)3-C6-haloalkynyl), preferably 3 to 4 carbon atoms (═ C)3-C4-haloalkynyl) and triple bonds in any position (as described above), in which some or all of the hydrogen atoms in these groups have been replaced by halogen atoms, in particular fluorine, chlorine and bromine, as described above.
As used hereinThe term "alkoxy" denotes in each case in general 1 to 8 carbon atoms (═ C)1-C8-alkoxy), often 1 to 6 carbon atoms (═ C)1-C6-alkoxy), preferably 1 to 4 carbon atoms (═ C)1-C4-alkoxy), in particular 1 or 2 carbon atoms (═ C)1-C2-alkoxy) which is linked to the rest of the molecule through an oxygen atom. C1-C2-alkoxy is methoxy or ethoxy. C1-C4Alkoxy is, in addition, for example, n-propoxy, 1-methylethoxy (isopropoxy), butoxy, 1-methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy) or 1, 1-dimethylethoxy (tert-butoxy). C1-C6Alkoxy is, in addition, for example, pentyloxy, 1-methylbutyloxy, 2-methylbutyloxy, 3-methylbutyloxy, 1-dimethylpropyloxy, 1, 2-dimethylpropyloxy, 2-dimethylpropyloxy, 1-ethylpropyloxy, hexyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 1-dimethylbutyloxy, 1, 2-dimethylbutyloxy, 1, 3-dimethylbutyloxy, 2-dimethylbutyloxy, 2, 3-dimethylbutyloxy, 3-dimethylbutyloxy, 1-ethylbutyloxy, 2-ethylbutyloxy, 1, 2-trimethylpropyloxy, 1,2, 2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy. C1-C8Alkoxy is, in addition, for example heptyloxy, octyloxy, 2-ethylhexyloxy and their positional isomers.
The term "haloalkoxy" as used herein denotes in each case a straight-chain or branched alkoxy group as defined above having 1 to 8 carbon atoms (═ C)1-C8Haloalkoxy), often having 1 to 6 carbon atoms (═ C)1-C6Haloalkoxy), preferably 1 to 4 carbon atoms (═ C)1-C4Haloalkoxy), more preferably 1 to 3 carbon atoms (═ C)1-C3Haloalkoxy), in particular 1 or 2 carbon atoms (═ C)1-C2Haloalkoxy), in which the hydrogen atoms of the radical are replaced (in this case) partially or completely by halogen atoms, in particular fluorine atomsIn this case, this group is also referred to as fluoroalkoxy). C1-C2Haloalkoxy is, for example, OCH2F、OCHF2、OCF3、OCH2Cl、OCHCl2、OCCl3Chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2, 2-difluoroethoxy, 2,2, 2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2, 2-difluoroethoxy, 2, 2-dichloro-2-fluoroethoxy, 2,2, 2-trichloroethoxy or OC2F5。C1-C4Haloalkoxy is, in addition, for example, 2-fluoropropoxy, 3-fluoropropoxy, 2-difluoropropoxy, 2, 3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2, 3-dichloropropoxy, 2-bromopropoxy, 3,3, 3-trifluoropropoxy, 3,3, 3-trichloropropoxy, OCH2-C2F5、OCF2-C2F5、1-(CH2F) -2-fluoroethoxy, 1- (CH)2Cl) -2-chloroethoxy, 1- (CH)2Br) -2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy. C1-C6Haloalkoxy is, in addition, for example, 5-fluoropentyloxy, 5-chloropentyloxy, 5-bromopentyloxy, 5-iodopentyloxy, undecafluoropentyloxy, 6-fluorohexyloxy, 6-chlorohexyloxy, 6-bromohexyloxy, 6-iodohexyloxy or dodecafluorohexyloxy.
The term "alkenyloxy" denotes an alkenyl group as defined above, which is attached to the rest of the molecule via an oxygen atom. C2-C6Alkenyloxy is C as defined above2-C6-an alkenyl group, which is attached to the rest of the molecule via an oxygen atom. C2-C8Alkenyloxy is C as defined above2-C8-an alkenyl group, which is attached to the rest of the molecule via an oxygen atom.
The term "haloalkenyloxy" denotes a haloalkenyl group as defined above which is attached to the rest of the molecule through an oxygen atom. C2-C6-haloalkenyloxy is C as defined above2-C6-halogenated alkenesA radical, which is linked to the rest of the molecule via an oxygen atom. C2-C8-haloalkenyloxy is C as defined above2-C8-haloalkenyl, which is attached to the rest of the molecule via an oxygen atom.
The term "alkynyloxy" denotes an alkynyl group as defined above, which is attached to the rest of the molecule through an oxygen atom. C2-C6-alkynyloxy is C as defined above2-C6-an alkynyl group, which is linked to the rest of the molecule through an oxygen atom. C2-C8-alkynyloxy is C as defined above2-C8-an alkynyl group, which is linked to the rest of the molecule through an oxygen atom.
The term "haloalkynyloxy" denotes a haloalkynyl group as defined above which is attached to the rest of the molecule via an oxygen atom. C2-C6-haloalkynyloxy is C as defined above2-C6-haloalkynyl which is linked to the rest of the molecule through an oxygen atom. C2-C8-haloalkynyloxy is C as defined above2-C8-haloalkynyl which is linked to the rest of the molecule through an oxygen atom. C3-C8-haloalkynyloxy is C as defined above3-C8-haloalkynyl which is linked to the rest of the molecule through an oxygen atom.
The term "alkoxy-alkyl" as used herein denotes in each case an alkyl group which generally comprises from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms, wherein 1 carbon atom carries an alkoxy group as defined above which generally comprises from 1 to 8, often from 1 to 6, in particular from 1 to 4, carbon atoms. The term "C1-C4-alkoxy-C1-C4-alkyl "means C as defined above1-C4-alkyl, wherein one hydrogen atom is C as defined above1-C4-alkoxy substitution. The term "C1-C6-alkoxy-C1-C6-alkyl "means C as defined above1-C6-alkyl, wherein one hydrogen atom is C as defined above1-C6-alkoxy substitution. Example is CH2OCH3、CH2-OC2H5N-propoxymethyl group, CH2-OCH(CH3)2N-butoxymethyl, (1-methylpropoxy) -methyl, (2-methylpropoxy) methyl, CH2-OC(CH3)32- (methoxy) ethyl, 2- (ethoxy) ethyl, 2- (n-propoxy) -ethyl, 2- (1-methylethoxy) -ethyl, 2- (n-butoxy) ethyl, 2- (1-methylpropoxy) -ethyl, 2- (2-methylpropoxy) -ethyl, 2- (1, 1-dimethylethoxy) -ethyl, 2- (methoxy) -propyl, 2- (ethoxy) -propyl, 2- (n-propoxy) -propyl, 2- (1-methylethoxy) -propyl, 2- (n-butoxy) -propyl, 2- (1-methylpropoxy) -propyl, 2- (2-methylpropoxy) -propyl, n-propylmethyl, n-propyl, 2- (1, 1-Dimethylethoxy) -propyl, 3- (methoxy) -propyl, 3- (ethoxy) -propyl, 3- (n-propoxy) -propyl, 3- (1-methylethoxy) -propyl, 3- (n-butoxy) -propyl, 3- (1-methylpropoxy) -propyl, 3- (2-methylpropoxy) -propyl, 3- (1, 1-Dimethylethoxy) -propyl, 2- (methoxy) -butyl, 2- (ethoxy) -butyl, 2- (n-propoxy) -butyl, 2- (1-methylethoxy) -butyl, 2- (n-butoxy) -butyl, 2- (1-methylpropoxy) -butyl, n-propoxy-propyl, n-propoxy-butyl, n-propoxy-propyl, n-propoxy-butyl, n, 2- (2-methyl-propoxy) -butyl, 2- (1, 1-dimethylethoxy) -butyl, 3- (methoxy) -butyl, 3- (ethoxy) -butyl, 3- (n-propoxy) -butyl, 3- (1-methylethoxy) -butyl, 3- (n-butoxy) -butyl, 3- (1-methylpropoxy) -butyl, 3- (2-methylpropoxy) -butyl, 3- (1, 1-dimethylethoxy) -butyl, 4- (methoxy) -butyl, 4- (ethoxy) -butyl, 4- (n-propoxy) -butyl, 4- (1-methylethoxy) -butyl, n-propyloxy) -butyl, n-butyloxy, n, 4- (n-butoxy) -butyl, 4- (1-methylpropoxy) -butyl, 4- (2-methylpropoxy) -butyl, 4- (1, 1-dimethylethoxy) -butyl, and the like.
The term "haloalkoxy-alkyl" as used herein denotes in each case an alkyl group as defined above, typically comprising 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, wherein 1 carbon atom carries a haloalkoxy group as defined above, typically comprising 1 to 8, often 1 to 6, in particular 1 to 4 carbon atoms, as defined above. Examples are fluoromethoxymethyl, difluoromethoxymethyl, trifluoromethoxy-methyl, 1-fluoroethoxymethyl, 2-fluoroethoxymethyl, 1-difluoroethoxymethyl, 1, 2-difluoroethoxymethyl, 2, 2-difluoroethoxymethyl, 1, 2-trifluoroethoxymethyl, 1,2, 2-trifluoroethoxymethyl, 2,2, 2-trifluoroethoxymethyl, pentafluoroethoxymethyl, 1-fluoroethoxy-1-ethyl, 2-fluoroethoxy-1-ethyl, 1-difluoroethoxy-1-ethyl, 1, 2-difluoroethoxy-1-ethyl, 2, 2-difluoroethoxy-1-ethyl, 1, 2-trifluoroethoxy-1-ethyl, 1-fluoroethoxy-1-ethyl, 1, 2-fluoroethoxy-1, 1,2, 2-trifluoroethoxy-1-ethyl, 2,2, 2-trifluoroethoxy-1-ethyl, pentafluoroethoxy-1-ethyl, 1-fluoroethoxy-2-ethyl, 2-fluoroethoxy-2-ethyl, 1-difluoroethoxy-2-ethyl, 1, 2-difluoroethoxy-2-ethyl, 2, 2-difluoroethoxy-2-ethyl, 1, 2-trifluoroethoxy-2-ethyl, 1,2, 2-trifluoroethoxy-2-ethyl, 2,2, 2-trifluoroethoxy-2-ethyl, pentafluoroethoxy-2-ethyl and the like.
The term "alkoxy-alkoxy" as used herein refers to an alkoxy group as defined above wherein one hydrogen atom is replaced by another alkoxy group as defined above. The term "C" as used herein1-C4-alkoxy-C1-C4-alkoxy "means an alkoxy group having 1 to 4 carbon atoms as defined above, wherein one hydrogen atom is replaced by C as defined above1-C4-alkoxy substitution. Examples are methoxymethoxy, ethoxymethoxy, propoxymethoxy, isopropoxymethoxy, n-butoxymethoxy, sec-butoxymethoxy, isobutoxymethoxy, tert-butoxymethoxy, 1-methoxyethoxy, 1-ethoxyethoxy, 1-propoxyethoxy, 1-isopropoxyethoxy, 1-n-butoxyethoxy, 1-sec-butoxyethoxy, 1-isobutoxyethoxy, 1-tert-butoxyethoxy, 2-methoxyethoxy, 2-ethoxyethoxy, 2-propoxyethoxy, 2-isopropoxyethoxy, 2-n-butoxyethoxy, 2-sec-butoxyethoxy, 2-isobutoxyethoxy, 2-tert-butoxyethoxy, 1-methoxypropoxy, 2-isopropoxy, 1-butoxyethoxy, 1-ethoxyethoxy, 1-isopropoxy, 1-ethoxypropoxy, 1-propoxypropoxy, 1-isopropoxypropoxy, 1-n-butoxypropoxy, 1-sec-butoxypropoxy, 1-isobutoxypropoxy, 1-tert-butoxypropoxy, 2-methoxypropoxy, 2-ethoxypropoxy, 2-propoxypropoxyOxy, 2-isopropoxypropoxy, 2-n-butoxypropoxy, 2-sec-butoxypropoxy, 2-isobutoxypropoxy, 2-tert-butoxypropoxy, 3-methoxypropoxy, 3-ethoxypropoxy, 3-propoxypropoxy, 3-isopropoxypropoxy, 3-n-butoxypropoxy, 3-sec-butoxypropoxy, 3-isobutoxypropoxy, 3-tert-butoxypropoxy and the like.
The term "haloalkoxy-alkoxy" denotes an alkoxy group wherein one hydrogen atom is replaced by an alkoxy group and wherein at least one, e.g. 1,2,3,4 or all remaining hydrogen atoms (which are hydrogen atoms in both alkoxy groups or in one of the alkoxy moieties) are replaced by a halogen atom. C1-C4-haloalkoxy-C1-C4Alkoxy is C1-C4Alkoxy in which one hydrogen atom is replaced by C1-C4Alkoxy substitution and wherein at least one, for example 1,2,3,4 or all remaining hydrogen atoms (which are hydrogen atoms in both alkoxy groups or one of the alkoxy moieties) are replaced by halogen atoms. An example is difluoromethoxymethoxy (CHF)2OCH2) Trifluoromethoxy, 1-difluoromethoxyethoxy, 1-trifluoromethoxyethoxy, 2-difluoromethoxyethoxy, 2-trifluoromethoxyethoxy, difluoro-methoxy (CH)3OCF2) 1, 1-difluoro-2-methoxyethoxy, 2-difluoro-2-methoxyethoxy, and the like.
"cycloalkoxy" means a cycloalkyl group, as defined above, attached to the rest of the molecule through an oxygen atom. C3-C7Examples of the cycloalkoxy group are cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy and cycloheptyloxy. C3-C10Examples of the-cycloalkoxy group include cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cycloheptyloxy, cyclooctyloxy, cyclononyloxy and cyclodecyloxy.
The term "cycloalkyl-alkoxy" as used herein refers to an alkoxy group as defined above wherein one hydrogen atom is replaced by a cycloalkyl group as defined above. The term "C" as used herein3-C10-cycloalkyl-C1-C2-alkoxy "means an alkoxy group having 1 or 2 carbon atoms as defined above, wherein one hydrogen atom is replaced by C as defined above3-C10-cycloalkyl substitution. Examples are cyclopropylmethoxy, cyclopropylethoxy, cyclobutylmethoxy, cyclobutylethoxy, cyclopentylmethoxy, cyclopentylethoxy, cyclohexylmethoxy, cyclohexylethoxy, cycloheptylmethoxy, cycloheptylethoxy, cyclooctylmethoxy, cyclooctylethoxy, cyclononylmethoxy, cyclononylethoxy, cyclodecylmethoxy and cyclodecylethoxy.
The term "cycloalkyl-alkoxy-alkyl" as used herein refers to an alkyl group as defined above wherein one hydrogen atom is replaced by an alkoxy group as defined above wherein in the alkoxy group one hydrogen atom is in turn replaced by a cycloalkyl group as defined above. The term "C" as used herein3-C6-cycloalkyl-C1-C6-alkoxy-C1-C6-alkyl "means an alkyl group as defined above having 1 to 6 carbon atoms, wherein one hydrogen atom is replaced by C as defined above1-C6-alkoxy in which one hydrogen atom is replaced by C as defined above3-C6-cycloalkyl substitution.
As used herein, the term "alkylthio" (also known as alkylsulfanyl, "alkyl-S" or "alkyl-S (O))k"(wherein k is 0) denotes in each case a compound as defined above which generally contains from 1 to 8 carbon atoms (═ C1-C8Alkylthio), often containing from 1 to 6 carbon atoms (═ C)1-C6Alkylthio), preferably 1 to 4 carbon atoms (═ C)1-C4Alkylthio) which is attached via a sulfur atom at any position in the alkyl group. C1-C2Alkylthio is methylthio or ethylthio. C1-C4Alkylthio is, in addition, for example, n-propylthio, 1-methylethylthio (isopropylthio), butylthio, 1-methylpropylthio (sec-butylthio), 2-methylpropylthio (isobutylthio) or 1, 1-dimethylethylthio (tert-butylthio). C1-C6Alkylthio is, in addition, for example, pentylthio, 1-methylbutylthio2-methylbutylthio, 3-methylbutylthio, 1-dimethylpropylthio, 1, 2-dimethylpropylthio, 2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1, 1-dimethylbutylthio, 1, 2-dimethylbutylthio, 1, 3-dimethylbutylthio, 2, 2-dimethylbutylthio, 2, 3-dimethylbutylthio, 3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1, 2-trimethylpropylthio, 1,2, 2-trimethylpropylthio, 1-ethyl-1-methylpropylthio or 1-ethyl-2-methylpropylthio. C1-C8Alkylthio is, in addition, for example heptylthio, octylthio, 2-ethylhexylthio and positional isomers thereof.
The term "haloalkylthio" as used herein refers to an alkylthio group as defined above wherein the hydrogen atoms are partially or fully replaced by fluorine, chlorine, bromine and/or iodine. C1-C2Haloalkylthio is, for example, SCH2F、SCHF2、SCF3、SCH2Cl、SCHCl2、SCCl3Chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2, 2-difluoroethylthio, 2,2, 2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2, 2-difluoroethylthio, 2, 2-dichloro-2-fluoroethylthio, 2,2, 2-trichloroethylthio or SC2F5。C1-C4Halogenalkylthio is, in addition, for example, 2-fluoropropylthio, 3-fluoropropylthio, 2-difluoropropylthio, 2, 3-difluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2, 3-dichloropropylthio, 2-bromopropylthio, 3,3, 3-trifluoropropylthio, 3,3, 3-trichloropropylthio, SCH2-C2F5、SCF2-C2F5、1-(CH2F) -2-fluoroethylthio, 1- (CH)2Cl) -2-chloroethylthio, 1- (CH)2Br) -2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or nonafluorobutylthio. C1-C6Haloalkylthio is, in addition, for example, 5-fluoropentylthio, 5-chloropentylthio, 5-bromopentylthio, 5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio, 6-chlorohexylthioThio, 6-bromohexylthio, 6-iodohexylthio or dodecafluorohexylthio.
As used herein, the terms "alkylsulfinyl" and "alkyl-S (O)k"(wherein k is 1) is the same, represents via sulfinyl group [ S (O)]The group is attached to an alkyl group as defined above. For example, the term "C1-C2-Alkylsulfinyl "means a sulfinyl [ S (O)]C as defined above attached to a radical1-C2-an alkyl group. The term "C1-C4-Alkylsulfinyl "means a sulfinyl [ S (O)]C as defined above attached to a radical1-C4-an alkyl group. The term "C1-C6-Alkylsulfinyl "means a sulfinyl [ S (O)]C as defined above attached to a radical1-C6-an alkyl group. C1-C2-alkylsulfinyl is methylsulfinyl or ethylsulfinyl. C1-C4Alkylsulfinyl is, in addition, for example, n-propylsulfinyl, 1-methylethylsulfinyl (isopropylsulfinyl), butylsulfinyl, 1-methylpropylsulfinyl (sec-butylsulfinyl), 2-methylpropylsulfinyl (isobutylsulfinyl) or 1, 1-dimethylethylsulfinyl (tert-butylsulfinyl). C1-C6Alkylsulfinyl is, in addition, for example, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 1-dimethylpropylsulfinyl, 1, 2-dimethylpropylsulfinyl, 2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1-dimethylbutylsulfinyl, 1, 2-dimethylbutylsulfinyl, 1, 3-dimethylbutylsulfinyl, 2-dimethylbutylsulfinyl, 2, 3-dimethylbutylsulfinyl, 2, 1-dimethylbutylsulfinyl, 2-methylpentylsulfinyl, 1, 2-dimethylbutylsulfinyl, 2,3, 3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1, 2-trimethylpropylsulfinyl, 1,2, 2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl.
As used hereinThe terms "alkylsulfonyl" and "alkyl-S (O)k"(wherein k is 2) is the same, represents a sulfonyl group [ S (O)2]The group is attached to an alkyl group as defined above. The term "C1-C2-alkylsulfonyl "means via sulfonyl [ S (O)2]C as defined above attached to a radical1-C2-an alkyl group. The term "C1-C4-alkylsulfonyl "means via sulfonyl [ S (O)2]C as defined above attached to a radical1-C4-an alkyl group. The term "C1-C6-alkylsulfonyl "means via sulfonyl [ S (O)2]C as defined above attached to a radical1-C6-an alkyl group. C1-C2-alkylsulfonyl is methylsulfonyl or ethylsulfonyl. C1-C4Alkylsulfonyl is, in addition, for example, n-propylsulfonyl, 1-methylethylsulfonyl (isopropylsulfonyl), butylsulfonyl, 1-methylpropylsulfonyl (sec-butylsulfonyl), 2-methylpropylsulfonyl (isobutylsulfonyl) or 1, 1-dimethylethylsulfonyl (tert-butylsulfonyl). C1-C6Alkylsulfonyl is, in addition, for example, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1-dimethylpropylsulfonyl, 1, 2-dimethylpropylsulfonyl, 2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1-dimethylbutylsulfonyl, 1, 2-dimethylbutylsulfonyl, 1, 3-dimethylbutylsulfonyl, 2-dimethylbutylsulfonyl, 2, 3-dimethylbutylsulfonyl, 3-dimethylbutylsulfonyl, tert-butylsulfonyl, 1-ethylbutylsulfonyl group, 2-ethylbutylsulfonyl group, 1, 2-trimethylpropylsulfonyl group, 1,2, 2-trimethylpropylsulfonyl group, 1-ethyl-1-methylpropylsulfonyl group or 1-ethyl-2-methylpropylsulfonyl group.
The term "alkylthio-alkyl" as used herein refers to a straight or branched chain alkyl group as defined above wherein one hydrogen atom is replaced by an alkylthio group as defined above. The term "C" as used herein1-C4-alkylthio-C1-C4-alkyl "means a linear or branched alkyl group as defined above having 1 to 4 carbon atoms, wherein one hydrogen atom is replaced by C as defined above1-C4-alkylthio substitution. Examples are methylthiomethyl, ethylthiomethyl, propylthiomethyl, isopropylthiomethyl, n-butylthiomethyl, sec-butylthiomethyl, isobutylthiomethyl, tert-butylthiomethyl, 1-methylthioethyl, 1-ethylthioethyl, 1-propylthioethyl, 1-isopropylthioethyl, 1-n-butylthioethyl, 1-sec-butylthioethyl, 1-isobutylthioethyl, 1-tert-butylthioethyl, 2-methylthioethyl, 2-ethylthioethyl, 2-propylthioethyl, 2-isopropylthioethyl, 2-n-butylthioethyl, 2-sec-butylthioethyl, 2-isobutylthioethyl, 2-tert-butylthioethyl, 1-methylthiopropyl, 1-ethylthiopropyl, 1-propylthiopropyl, 1-isopropylthiopropylthiopropylpropyl, 1-n-butylmercaptopropyl, 1-sec-butylmercaptopropyl, 1-isobutylmercaptopropyl, 1-tert-butylmercaptopropyl, 2-methylthiopropyl, 2-ethylmercaptopropyl, 2-propylmercaptopropyl, 2-isopropylmercaptopropyl, 2-n-butylmercaptopropyl, 2-sec-butylmercaptopropyl, 2-isobutylmercaptopropyl, 2-tert-butylmercaptopropyl, 3-methylthiopropyl, 3-ethylmercaptopropyl, 3-propylmercaptopropyl, 3-isopropylmercaptopropyl, 3-n-butylmercaptopropyl, 3-sec-butylmercaptopropyl, 3-isobutylmercaptopropyl, 3-tert-butylmercaptopropyl, and the like.
The term "alkylthio-alkylthio" as used herein refers to an alkylthio group as defined above wherein one hydrogen atom is replaced by an alkylthio group as defined above. The term "C" as used herein1-C4-alkylthio-C1-C4By "alkylthio" is meant an alkylthio group as defined above having 1 to 4 carbon atoms in which one hydrogen atom is replaced by C as defined above1-C4-alkylthio substitution. Examples are methylthiomethylthio, ethylthiomethyl, propylthiomethyl, isopropylthiomethyl, n-butylthiomethyl, sec-butylthiomethyl, isobutylthiomethyl, tert-butylthiomethyl, 1-methylthioethylthio, 1-ethylthioethylthio, 1-propylthioethylthio, 1-isopropylthioethylthio, 1-n-butylthioethylthio, 1-sec-butylthioethylthio, 1-isobutylthioethylthio, 1-tert-butylthioethylthio, 2-methylthioethylthio,2-ethylthioethylthio, 2-propylthioethylthio, 2-isopropylthioethylthio, 2-n-butylthioethylthio, 2-sec-butylthioethylthio, 2-isobutylthioethylthio, 2-tert-butylthioethylthio, 1-methylthiopropylthio, 1-ethylthiopropylthio, 1-propylthiopropylthio, 1-isopropylthiopropylthio, 1-n-butylthiopropylthio, 1-sec-butylthiopropylthio, 1-isobutylthiopropylthio, 1-tert-butylthiopropylthio, 2-methylthiopropylthio, 2-ethylthiopropylthio, 2-propylthiopropylthio, 2-isopropylthiopropylthio, 2-n-butylthiopropylthio, 2-sec-butylthiopropylthio, 2-isobutylthiopropylthio, 2-tert-butylthiopropylthio, 3-methylthiopropylthio, 3-ethylthiopropylthio, 3-propylthiopropylthio, 3-isopropylthiopropylthio, 3-n-butylthiopropylthio, 3-sec-butylthiopropylthio, 3-isobutylthiopropylthio, 3-tert-butylthiopropylthio and the like.
The term "alkylamino" as used herein denotes in each case the group R HN-, wherein R is usually a group having from 1 to 6 carbon atoms (═ C)1-C6Alkylamino), preferably 1 to 4 carbon atoms (═ C)1-C4-alkylamino) or 1 to 3 carbon atoms (═ C1-C3-alkylamino) groups. C1-C3Examples of-alkylamino are methylamino, ethylamino, n-propylamino and isopropylamino. C1-C4Examples of-alkylamino radicals other than for C1-C3In addition to those mentioned for alkylamino, there are n-butylamino, 2-butylamino, isobutylamino and tert-butylamino.
The term "dialkylamino" as used herein denotes in each case a radical R × R ° N-, wherein R × and R ° independently of one another are straight-chain or branched alkyl radicals, each of which usually has from 1 to 6 carbon atoms (═ di- (C)1-C6-alkyl) -amino), preferably 1 to 4 carbon atoms (═ di- (C)1-C4-alkyl) -amino) or 1 to 3 carbon atoms (═ di- (C)1-C3-alkyl) -amino). Di- (C)1-C3Examples of (alkyl) -amino are dimethylamino, diethylamino, dipropylamino, methyl-ethyl-amino, methyl-propyl-amino, methyl-isopropylamino, ethylPropyl-amino, ethyl-isopropylamino and the like. Di- (C)1-C4Examples of-alkyl) -amino are dimethylamino, diethylamino, dipropylamino, dibutylamino, methyl-ethyl-amino, methyl-propyl-amino, methyl-isopropylamino, methyl-butyl-amino, methyl-isobutyl-amino, ethyl-propyl-amino, ethyl-isopropylamino, ethyl-butyl-amino, ethyl-isobutyl-amino and the like.
Substituent "oxo" replaces CH by a C (═ O) group2A group.
The suffix "— carbonyl" in a group denotes in each case that the group is linked to the remainder of the molecule via a carbonyl C ═ O group. Examples of such a case include alkylcarbonyl, haloalkylcarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxycarbonyl and haloalkoxycarbonyl.
The term "alkylcarbonyl" denotes alkyl as defined above, through carbonyl [ C (═ O)]The group is attached to the rest of the molecule. C1-C3-alkylcarbonyl is C as defined above1-C3-alkyl, via carbonyl [ C (═ O)]The group is attached to the rest of the molecule. C1-C4-alkylcarbonyl is C as defined above1-C4-alkyl, via carbonyl [ C (═ O)]The group is attached to the rest of the molecule. C1-C3Examples of-alkylcarbonyl are acetyl (methylcarbonyl), propionyl (ethylcarbonyl), propylcarbonyl and isopropylcarbonyl. C1-C4Examples of-alkylcarbonyl are acetyl (methylcarbonyl), propionyl (ethylcarbonyl), propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl and the like.
Alkylene or alkanediyl is a straight-chain or branched divalent alkyl group. C1-C3Alkylene or C1-C3Alkanediyl is a linear or branched divalent alkyl radical having 1,2 or 3 carbon atoms. Examples are-CH2-、-CH2CH2-、-CH(CH3)-、-CH2CH2CH2-、-CH(CH3)CH2-、-CH2CH(CH3) -and-C (CH)3)2-。C1-C4Alkylene or C1-C4Alkanediyl is a linear or branched divalent alkyl radical having 1,2,3 or 4 carbon atoms. Examples are-CH2-、-CH2CH2-、-CH(CH3)-、-CH2CH2CH2-、-CH(CH3)CH2-、-CH2CH(CH3)-、-C(CH3)2-、-CH2CH2CH2CH2-、-CH(CH3)CH2CH2-、-CH2CH2CH(CH3)-、-C(CH3)2CH2-and-CH2C(CH3)2-. Straight chain C1-C4Alkylene or C1-C4An example of an-alkanediyl group is-CH2-、-CH2CH2-、-CH2CH2CH2-and-CH2CH2CH2CH2-。C2-C4Alkylene or C2-C4Alkanediyl is a linear or branched divalent alkyl radical having 2,3 or 4 carbon atoms. Examples are-CH2CH2-、-CH(CH3)-、-CH2CH2CH2-、-CH(CH3)CH2-、-CH2CH(CH3)-、-C(CH3)2-、-CH2CH2CH2CH2-、-CH(CH3)CH2CH2-、-CH2CH2CH(CH3)-、-C(CH3)2CH2-and-CH2C(CH3)2-。C3-C5Alkylene or C3-C5Alkanediyl is a linear or branched divalent alkyl radical having 3,4 or 5 carbon atoms. Examples are-CH2CH2CH2-、-CH(CH3)CH2-、-CH2CH(CH3)-、-C(CH3)2-、-CH2CH2CH2CH2-、-CH(CH3)CH2CH2-、-CH2CH2CH(CH3)-、-C(CH3)2CH2-、-CH2C(CH3)2-、-(CH2)5-and the like.
The term "aryl" as used herein refers to a mono-, bi-or tricyclic aromatic hydrocarbon group, such as phenyl or naphthyl, especially phenyl.
Phenoxy is a benzene ring attached through an oxygen atom.
The term "heteroaryl" as used herein refers to a mono-, bi-or tricyclic heteroaromatic hydrocarbon group, preferably a monocyclic heteroaromatic group, such as pyridyl, pyrimidinyl, and the like.
The heterocyclic or heterocyclic group may be saturated, partially unsaturated, or maximally unsaturated, if not otherwise specified.
The term "3-, 4-, 5-or 6-membered monocyclic or 8-, 9-or 10-membered bicyclic saturated, unsaturated or aromatic heterocyclic ring containing 1,2,3 or 4 heteroatoms as ring members selected from N, O and S" as used herein denotes a monocyclic or bicyclic group which is saturated, unsaturated or aromatic, wherein N may optionally be oxidized, i.e. in the form of an N-oxide, and S may also optionally be oxidized to various oxidation states, i.e. in SO or SO2In the form of (1). The unsaturated heterocycle contains at least one C-C and/or C-N and/or N-N double bond. The partially unsaturated ring contains less than the maximum number of C-C and/or C-N and/or N-N double bonds allowed by the ring size. Fully (or maximally) unsaturated heterocycles contain as many conjugated C-C and/or C-N and/or N-N double bonds as the ring size allows. The most unsaturated 5-or 6-membered heteromonocyclic ring is usually aromatic. With the exception of containing O, S, SO and/or SO2The most unsaturated 6-membered rings that are ring members, such as pyran and thiopyran, are not aromatic. Thus, an aromatic monocyclic heterocycle is a monocyclic heterocycle which contains one or more nitrogen atoms as ring members and which does not contain O, S, SO and/or SO2A fully unsaturated 5-membered monocyclic heterocyclic ring or a fully unsaturated 6-membered monocyclic heterocyclic ring as a ring member. An aromatic bicyclic heterocycle is an 8, 9 or 10 membered bicyclic heterocycle consisting of a 5 or 6 membered heteroaromatic ring fused to a phenyl ring or to another 5 or 6 membered heteroaromatic ring. The heterocyclic ring may be attached to the rest of the molecule through a carbon ring member or through a nitrogen ring member. Of course, a heterocycle contains at least one carbon ring atom. Such asIf the fruit ring contains more than one O ring atom, then these atoms are not adjacent.
Examples of 3-, 4-, 5-or 6-membered monocyclic saturated heterocycles include: oxiranen-2-yl, aziridin-1-yl, aziridin-2-yl, oxetan-2-yl, azetidin-1-yl, azetidin-2-yl, azetidin-3-yl, thietane-1-yl, thietane-2-yl, thietane-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothien-2-yl, tetrahydrothien-3-yl, pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-3-yl, pyrazolidin-1-yl, pyrazolidin-3-yl, pyrazolidin-4-yl, pyrazolidin-2-yl, azetidin-1-yl, azetidin-3-yl, and pyrrolidin-1-yl, Pyrazolidin-5-yl, imidazolidin-1-yl, imidazolidin-2-yl, imidazolidin-4-yl, oxazolidin-2-yl, oxazolidin-3-yl, oxazolidin-4-yl, oxazolidin-5-yl, isoxazolidin-2-yl, isoxazolidin-3-yl, isoxazolidin-4-yl, isoxazolidin-5-yl, thiazolidin-2-yl, thiazolidin-3-yl, thiazolidin-4-yl, thiazolidin-5-yl, isothiazolidin-2-yl, isothiazolidin-3-yl, isothiazolidin-4-yl, isothiazolidin-5-yl, 1,2, 4-oxadiazolidin-3-yl, imidazolidin-2-yl, thiazolidin-3-yl, and the like, 1,2, 4-oxadiazolidin-5-yl, 1,2, 4-thiadiazolidin-3-yl, 1,2, 4-thiadiazolidin-5-yl, 1,2, 4-triazolidin-3-yl, 1,3, 4-oxadiazolidin-2-yl, 1,3, 4-thiadiazolidin-2-yl, 1,3, 4-triazolidin-1-yl, 1,3, 4-triazolidin-2-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 1, 3-dioxan-5-yl, 1, 4-dioxan-2-yl, piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, Hexahydropyridazin-3-yl, hexahydropyridazin-4-yl, hexahydropyrimidin-2-yl, hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl, piperazin-1-yl, piperazin-2-yl, 1,3, 5-hexahydrotriazin-1-yl, 1,3, 5-hexahydrotriazin-2-yl and 1,2, 4-hexahydrotriazin-3-yl, morpholin-2-yl, morpholin-3-yl, morpholin-4-yl, thiomorpholin-2-yl, thiomorpholin-3-yl, thiomorpholin-4-yl, 1-oxothiomorpholin-2-yl, 1-oxothiomorpholin-3-yl, 1-oxothiomorpholin-4-yl, methyl-ethyl, ethyl, 1, 1-two oxygen sulfur morpholine-2-yl, 1-two oxygen sulfur morpholine-3-yl, 1-two oxygen sulfur morpholine-4-yl etc..
Examples of 5-or 6-membered monocyclic partially unsaturated heterocycles include: 2, 3-dihydrofuran-2-yl, 2, 3-dihydrofuran-3-yl, 2, 4-dihydrofuran-2-yl, 2, 4-dihydrofuran-3-yl, 2, 3-dihydrothien-2-yl, 2, 3-dihydrothien-3-yl, 2, 4-dihydrothien-2-yl, 2, 4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 3-dihydrofuran-2-yl, 2, 4-dihydrothien-3-yl, 2, 4-dihydrothien-2-yl, 2, 4-dihydrothien-3-yl, 2, 4-dihydro, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2, 3-dihydropyrazol-1-yl group, 2, 3-dihydropyrazol-2-yl group, 2, 3-dihydropyrazol-3-yl group, 2, 3-dihydropyrazol-4-yl group, 2, 3-dihydropyrazol-5-yl group, 3, 4-dihydropyrazol-1-yl group, 3, 4-dihydropyrazol-3-yl group, 3, 4-dihydropyrazol-4-yl group, 3, 4-dihydropyrazol-5-yl group, 4, 5-dihydropyrazol-1-yl group, 4, 5-dihydropyrazol-3-yl group, 4, 5-dihydropyrazol-4-yl group, 4, 5-dihydropyrazol-5-yl group, 2, 3-dihydrooxazol-2-yl group, 2, 3-dihydropyrazol-3-yl group, 2, 3-dihydropyrazol-4-yl group, 2, 3-dihydrooxazol-3-yl, 2, 3-dihydrooxazol-4-yl, 2, 3-dihydrooxazol-5-yl, 3, 4-dihydrooxazol-2-yl, 3, 4-dihydrooxazol-3-yl, 3, 4-dihydrooxazol-4-yl, 3, 4-dihydrooxazol-5-yl, 3, 4-dihydrooxazol-2-yl, 3, 4-dihydrooxazol-3-yl, 3, 4-dihydrooxazol-4-yl, 2-, 3-, 4-, 5-or 6-di-or tetrahydropyridinyl, 3-di-or tetrahydropyridazinyl, 4-di-or tetrahydropyridazinyl, 2-di-or tetrahydropyrimidinyl, pyridinyl, or a mixture thereof, 4-di-or tetrahydropyrimidinyl, 5-di-or tetrahydropyrimidinyl, di-or tetrahydropyrazinyl, 1,3, 5-di-or tetrahydrotriazin-2-yl and 1,2, 4-di-or tetrahydrotriazin-3-yl.
A5-or 6-membered monocyclic fully unsaturated (including aromatic) heterocyclic ring is, for example, a 5-or 6-membered monocyclic fully unsaturated (including aromatic) heterocyclic ring. Examples are: 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 1,3, 4-triazol-1-yl, 1,3, 4-triazol-2-yl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 1-oxopyridin-2-yl, 1-oxopyridin-3-yl, 1-oxopyridin-4-yl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl.
Examples of the 5-or 6-membered heteroaromatic ring fused with a benzene ring or a 5-or 6-membered heteroaryl group include benzofuranyl, benzothienyl, indolyl, indazolyl, benzimidazolyl, benzoxazolyl, benzooxadiazolyl, benzothiadiazolyl, benzoxazinyl, quinolyl, isoquinolyl, purinyl, 1, 8-naphthyridinyl, pteridinyl, pyrido [3,2-d ] pyrimidinyl or pyridoimidazolyl and the like.
If two radicals are bound to the same nitrogen atom (e.g. R)2aAnd R2bOr R3cAnd R3dOr R3eAnd R3fOr R3gAnd R3hOr R4eAnd R4fOr R4gAnd R4h) Together with the nitrogen atom to which they are attached form a 4-, 5-, 6-, 7-or 8-membered saturated or unsaturated N-linked heterocyclic group which may contain as ring members other heteroatoms selected from O, S and N, which are e.g. azetidin-1-yl, pyrrolidin-1-yl, pyrazolidin-1-yl, imidazolidin-1-yl, oxazolidin-3-yl, thiazolidin-3-yl, isoxazolidin-2-yl, isothiazolin-2-yl, [1,2,3 ] or a salt thereof]-triazolidin-1-yl, [1,2,3]-triazolidin-2-yl, [1,2,4 ]]-triazolidin-1-yl, [1,2,4]-triazolidin-4-yl, [1,2,3]Oxadiazolidin-2-yl, [1,2,3 ] methyl]Oxadiazolidin-3-yl, [1,2,5 ] methyl]Oxadiazolidin-2-yl, [1,2,4 ] methyl]Oxadiazolidin-2-yl, [1,2,4 ] methyl]Oxadiazolidin-4-yl, [1,3,4 ] methyl]Oxadiazolidin-3-yl, [1,2,3 ] methyl]-thiadiazolidin-2-yl, [1,2,3]-thiadiazolidin-3-yl, [1,2,5]-thiadiazolidin-2-yl, [1,2,4]-thiadiazolidin-2-yl, [1,2,4]-thiadiazolidin-4-yl, [1,3,4]-thiadiazolidin-3-yl, piperidin-1-yl, piperazin-1-yl, morpholin-1-yl, thiomorpholin-1-yl, 1-oxothiomorpholin-1-yl, 1-dioxothiomorpholin-1-yl, azepan-1-yl, 1, 4-diazepan-1-yl, pyrrolin-1-yl, pyrazolin-1-yl, imidazolin-1-yl, oxazolin-3-yl, isoxazolin-2-yl, thiazolin-3-yl, isothiazolin-1-yl, 1, 2-dihydropyridin-1-yl, 1,2,3, 4-tetrahydropyridin-1-yl, 1,2,5, 6-tetrahydropyridin-1-yl, 1, 2-dihydropyridazine, 1, 6-dihydropyridazine, 1,2,3, 4-tetrahydropyridazin-1-yl, 1,2,5, 6-tetrahydropyridazin-1-yl, 1, 2-dihydropyrimidine, pyridinylpyrimidine, pyridinylpyridazine,1, 6-dihydropyrimidine, 1,2,3, 4-tetrahydropyrimidin-1-yl, 1,2,5, 6-tetrahydropyrimidin-1-yl, 1, 2-dihydropyrazin-1-yl, 1,2,3, 4-tetrahydropyrazin-1-yl, 1,2,5, 6-tetrahydropyrazin-1-yl, pyrrol-1-yl, pyrazol-1-yl, imidazol-1-yl, [1,2, 3-tetrahydropyrimidin-1-yl]-1H-triazol-1-yl, [1,2,3]-2H-triazol-2-yl, [1,2,4 ]]-1H-triazol-1-yl and [1,2,4 ]]-4H-triazol-4-yl.
The following explanations of preferred embodiments of the variables (substituents) of the compounds of formula I are valid both individually and preferably in combination with each other and also in combination with the stereoisomers, salts or tautomers thereof.
The following description of preferred embodiments of the variables, where applicable, is valid both individually and preferably in combination with one another in the case of the compounds of the formula I and also in the case of the use and the process according to the invention and the compositions according to the invention.
Preferred compounds of the invention are compounds of formula I, including stereoisomers thereof, or N-oxides or salts thereof, wherein the salts are agriculturally acceptable salts.
According to group 1 of embodiments of the invention, the variable Q in the compound of formula I is Q1:
Wherein in the formula Q1And # in (b) represents the point of attachment to the nitrogen atom. Wherein Q is Q1Has the structure of formula I.A, wherein the variable R1、Z2、R2a、R2b、R2c、R3、R4、R5、R6aAnd R7As defined herein:
according to another group 2 of embodiments of the invention, the variable Q in the compounds of formula I is Q2:
Wherein in the formula Q2And # in (b) represents the point of attachment to the nitrogen atom. Wherein Q is Q2Has the formula I.B, wherein the variable R1、Z2、R2a、R2b、R2c、R3、R4、R5、R6bAnd R7As defined herein:
according to another group 3 of embodiments of the invention, the variable Q in the compounds of formula I is Q3:
Wherein in the formula Q3And # in (b) represents the point of attachment to the nitrogen atom. Wherein Q is Q3Has the structure of formula I.C, wherein the variable R1、Z2、R2a、R2b、R2c、R3、R4、R5、R6cAnd R7As defined herein:
according to yet another group 4 of embodiments of the invention, the variable Q in the compounds of formula I is Q4:
Wherein in the formula Q4And # in (b) represents the point of attachment to the nitrogen atom. Wherein Q is Q4Has the structure of formula I.D, wherein the variable R1、Z2、R2a、R2b、R2c、R3、R4、R5、R6dAnd R7As herein describedDefined as follows:
among the compounds of the formula I, their N-oxides and their agriculturally useful salts, particular preference is given to the compounds of embodiment group 1.
Of the compounds of the formula I, their N-oxides and their agriculturally suitable salts, particular preference is also given to the compounds of group 2 of the embodiments.
Of the compounds of the formula I, their N-oxides and their agriculturally suitable salts, particular preference is also given to the compounds of group 4 of the embodiments.
In particular, the compounds of formula I are compounds of formula I.A, wherein Q is Q1(group 1).
The compounds of the formula I according to the invention are preferably selected from the group consisting of the compounds of the formulae I.A, I.B, I.C and I.D, the N-oxides thereof and the agriculturally suitable salts thereof, where the variable R1、Z2、R2a、R2b、R2c、R3、R4、R5、R7And R6a、R6b、R6cOr R6dAs defined herein, in particular, have the preferred meanings given below. The following preferred meanings apply in the same manner to each of groups 1,2,3 and 4 of embodiments.
A particular group of compounds of the invention are compounds of formulae I, I.A, I.B, I.C and I.D, their N-oxides and their salts, wherein Z is2Is a covalent bond, i.e. a covalent single bond, and R7Is H, these compounds are hereinafter referred to as compounds of formula I ', i.a ', I.B ', i.c ' and i.d ', respectively.
Another particular group of the inventionThe compounds are of the formulae I, I.A, I.B, I.C and I.D, their N-oxides and their salts, wherein Z2Is a divalent radical, in particular straight-chain C1-C4Alkanediyl, especially-CH2-or-CH2CH2-。
Preferred compounds of the invention are compounds of the formulae I, I.A, I.B, I.C and I.D, and also compounds of the formulae I ', I.A ', I.B ', I.C ' and I.D ', their N-oxides and their salts, where R is1Selected from cyano, halogen, nitro, C1-C6Alkyl radical, C1-C6-haloalkyl group, C1-C4-alkoxy-C1-C4Alkyl radical, C1-C4-haloalkoxy-C1-C4Alkyl radical, C1-C6-alkoxy, C1-C4-alkoxy-C1-C4-alkoxy-Z1、R1b-S(O)k-Z1Wherein k and Z1As defined herein, and wherein R1bAs defined above, in particular selected from C1-C4-alkyl and C1-C4-haloalkyl. In this text Z1In particular a covalent bond.
More preferably, R in formula I, I.A, I.B, I.C, I.D, I ', I.A', I.B ', I.C' and I.D1Selected from halogen, nitro, cyano, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkoxy-Z1And R1b-S(O)k-Z1Wherein k and Z1As defined herein, and wherein R1bAs defined above, in particular selected from C1-C4-alkyl and C1-C4-haloalkyl. In this text Z1In particular a covalent bond.
In particular, R in the formulae I, I.A, I.B, I.C, I.D, I ', I.A', I.B ', I.C' and I.D1Selected from halogen, nitro, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkoxy-C1-C4Alkyl radical, C1-C4Alkylthio radical, C1-C4-haloalkylthio and C1-C4-an alkylsulfonyl group. In particular, R in formula I, I.A, I.B, I.C, I.D, I ', I.A', I.B ', I.C' and I.D1Selected from F, Cl, Br, I, nitro, CH3、CF3、OCH3、SCH3、SCF3、SO2CH3And CH2OCH2CH2OCH3. More specifically, R in formulas I, I.A, I.B, I.C, I.D, I ', I.A', I.B ', I.C' and I.D1Selected from F, Cl, Br, I, nitro, CH3、CF3、OCH3、SCH3And SO2CH3Even more specifically R in formulas I, I.A, I.B, I.C, I.D, I ', I.A', I.B ', I.C' and I.D1Selected from Cl, Br, CH3、CF3And OCH3Especially R in the formulae I, I.A, I.B, I.C, I.D, I ', I.A', I.B ', I.C' and I.D1Is Cl or CH3。
In another embodiment, R in formula I, I.A, I.B, I.C, I.D, I ', I.A', I.B ', I.C' and I.D1Selected from halogen, C1-C4-alkyl and C1-C4-alkoxy groups. More specifically, R in formulas I, I.A, I.B, I.C, I.D, I ', I.A', I.B ', I.C' and I.D1Selected from Cl, Br, CH3And OCH3More particularly Cl, CH3And OCH3Very particularly Cl or CH3。
Preferred compounds of the invention are compounds of the formulae I, I.A, I.B, I.C and I.D, and also compounds of the formulae I ', I.A ', I.B ', I.C ' and I.D ', their N-oxides and their salts, where R is2aSelected from hydrogen, C1-C6Alkyl radical, C1-C6-alkoxy, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4Alkyl radical, C1-C6-haloalkylPhenyl, benzyl and heterocyclyl, where heterocyclyl is a 5-or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1,2,3 or 4 heteroatoms selected from O, N and S as ring members, where phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1,2,3 or 4 identical or different radicals R21Is substituted, and wherein R21Preferably selected from halogen, CN, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-haloalkoxy, and wherein R21In particular from halogen, C1-C4-alkyl, fluoro C1-C2Alkyl radical, C1-C4Alkoxy and fluoro C1-C2Alkoxy, in particular selected from halogen, methyl and methoxy.
Preferred are compounds of the invention in which the radicals R in the formulae I, I.A, I.B, I.C, I.D, I ', I.A', I.B ', I.C' and I.D2aIs not hydrogen.
At R2aIn the context of (a), heterocyclyl is in particular a 5-or 6-membered monocyclic saturated or aromatic heterocycle which comprises 1,2 or 3 heteroatoms selected from O, N and S as ring members. Heterocyclyl in this context is in particular a 5-or 6-membered monocyclic aromatic heterocycle which comprises 1 or 2 heteroatoms selected from O, N and S as ring members;
in formulae I, I.A, I.B, I.C, I.D, I ', I.A ', I.B ', I.C ' and I.D ', R2aIn particular from C1-C4Alkyl radical, C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkyl-methyl, fluoro C1-C4Alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1,2,3 or 4 identical or different radicals R21Is substituted, and wherein R21Preferably selected from halogen, CN, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-haloalkoxy, and wherein R21In particular from halogen, C1-C4-alkyl, fluoro C1-C2Alkyl radical, C1-C4Alkoxy and fluoro C1-C2Alkoxy, in particular selected from halogen, methyl and methoxy.
In formulae I, I.A, I.B, I.C, I.D, I ', I.A ', I.B ', I.C ' and I.D ', R2aMore particularly from C1-C4Alkyl radical, C3-C7-cycloalkyl, fluoro C1-C4Alkyl radical, C1-C4Alkoxy and phenyl, where phenyl is unsubstituted or substituted by 1 or 2 radicals R21Substituted, said R21Are identical or different and are preferably selected from halogen, C1-C4-alkyl, fluoro C1-C2Alkyl radical, C1-C4Alkoxy and fluoro C1-C2Alkoxy, in particular selected from halogen, methyl and methoxy.
In formulae I, I.A, I.B, I.C, I.D, I ', I.A ', I.B ', I.C ' and I.D ', R2aEven more particularly from C1-C4-alkyl, fluoro C1-C2Alkyl radical, C3-C4-cycloalkyl and phenyl, said phenyl being unsubstituted or substituted by 1,2 or 3 substituents selected from halogen, C1-C4-alkyl, fluoro C1-C2Alkyl radical, C1-C4Alkoxy and fluoro C1-C2The radical R of an alkoxy group21And wherein phenyl is in particular unsubstituted or substituted by 1,2 or 3 groups selected from halogen, methyl and methoxy.
In formulae I, I.A, I.B, I.C, I.D, I ', I.A ', I.B ', I.C ' and I.D ', R2aIn particular from methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2-、CF3CH2-、CH3O-, 4-Cl-phenyl, 4-methoxyphenyl, 4-methylphenyl and 2, 6-dimethylphenyl.
In another even more particular embodiment, in formulas I, i.a, I.B, i.c, i.d, I ', i.a ', I.B ', i.c ' and i.d ', R2aIs selected from C1-C6Alkyl radical, C3-C6-cycloalkyl, C1-C4Haloalkyl and phenyl, wherein phenyl is unsubstituted or substituted by 1,2,3 or 4 identical or different C1-C4-alkyl substitution. More preferably, R2aIs selected from C1-C4Alkyl radical, C3-C6-cycloalkyl, fluoro C1-C4-alkyl and phenyl, said phenyl being unsubstituted or substituted with 1,2,3 or 4 methyl groups. Even more preferably, R2aIs selected from C1-C4Alkyl radical, C3-C4-cycloalkyl, fluoro C1-C2-alkyl and phenyl, said phenyl being unsubstituted or substituted with 1,2 or 3 methyl groups. Specifically, R2aIs selected from C1-C4Alkyl, cyclopropyl, fluoro C1-C2-alkyl and phenyl, said phenyl being unsubstituted or substituted with 1 or 2 methyl groups.
Preferred compounds of the invention are compounds of the formulae I, I.A, I.B, I.C and I.D, and also compounds of the formulae I ', I.A ', I.B ', I.C ' and I.D ', their N-oxides and their salts, where R is2bSelected from hydrogen, C1-C6Alkyl radical, C1-C6-alkoxy, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4Alkyl radical, C1-C6Haloalkyl, phenyl, benzyl and heterocyclyl, wherein heterocyclyl is a 5-or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1,2,3 or 4 heteroatoms selected from O, N and S as ring members, wherein phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1,2,3 or 4 identical or different radicals R21Is substituted, and wherein R21Preferably selected from halogen, CN, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-haloalkoxy, and wherein R21In particular from halogen, C1-C4-alkyl, fluoro C1-C2Alkyl radical, C1-C4Alkoxy and fluoro C1-C2Alkoxy, in particular selected from halogen, methyl and methoxy.
Preferred are compounds of the invention in which the radicals R in the formulae I, I.A, I.B, I.C, I.D, I ', I.A', I.B ', I.C' and I.D2bIs not hydrogen.
At R2bIn the context of (a), heterocyclyl is in particular a 5-or 6-membered monocyclic saturated or aromatic heterocycle which comprises 1,2 or 3 heteroatoms selected from O, N and S as ring members. Heterocyclyl in this context is in particular a 5-or 6-membered monocyclic aromatic heterocycle which comprises 1 or 2 heteroatoms selected from O, N and S as ring members.
In formulae I, I.A, I.B, I.C, I.D, I ', I.A ', I.B ', I.C ' and I.D ', R2bIn particular from hydrogen, C1-C4Alkyl radical, C3-C6-cycloalkyl, C3-C6-cycloalkyl-methyl and fluoro C1-C4-an alkyl group.
In formulae I, I.A, I.B, I.C, I.D, I ', I.A ', I.B ', I.C ' and I.D ', R2bMore particularly from hydrogen, C1-C4Alkyl radical, C3-C7-cycloalkyl and fluoro C1-C4-an alkyl group.
In formulae I, I.A, I.B, I.C, I.D, I ', I.A ', I.B ', I.C ' and I.D ', R2bEven more particularly from hydrogen, C1-C4-alkyl, fluoro C1-C2-alkyl and C3-C4-a cycloalkyl group.
In formulae I, I.A, I.B, I.C, I.D, I ', I.A ', I.B ', I.C ' and I.D ', R2bIn particular from hydrogen, methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2And CF3CH2-。
In an alternative particular embodiment, in formulas I, I.A, I.B, I.C, I.D, I ', I.A ', I.B ', I.C ' and I.D ', R is2bSelected from hydrogen, C1-C4-alkyl and C3-C6Cycloalkyl, more preferably selected from hydrogen, C1-C3-alkyl and C3-C4-a cycloalkyl group. Specifically, R2bSelected from hydrogen, C1-C3-alkyl and cyclopropyl.
Also preferred are compounds of formula I, I.A, I.B, I.C, I.D, I ', I.A ', I.B ', I.C ' and I.D ', their N-oxides and their salts, wherein R is2aAnd R2bTogether with the nitrogen atom to which they are attached form a 4-, 5-, 6-or 7-membered saturated or unsaturated heterocyclic radical which may contain a further heteroatom selected from O, S and N as a ring member and which is unsubstituted or may carry 1,2,3 or 4 radicals R2dSaid R is2dAre identical or different and are selected, in particular, from ═ O, OH, halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-haloalkoxy. Of these, particular preference is given to those in which the variables R in the formulae I, I.A, I.B, I.C, I.D, I ', I.A ', I.B ', I.C ' and I.D ' are present2aAnd R2bThose compounds which, together with the nitrogen atom to which they are attached, may form a 5-or 6-membered saturated or unsaturated heterocyclic radical which may contain a further heteroatom selected from O, S and N as a ring member and which is unsubstituted or may carry 1,2,3 or 4 radicals R2dSaid R is2dAre identical or different and are selected in particular from ═ O, halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-haloalkoxy. Of these, particular preference is given to those in which the variables R in the formulae I, I.A, I.B, I.C, I.D, I ', I.A ', I.B ', I.C ' and I.D ' are present2aAnd R2bTogether with the nitrogen atom to which they are bound form 4-morpholinyl, 4-thiomorpholinyl, 1-piperidinyl and 1-pyrrolidinyl, where 4-morpholinyl, 4-thiomorpholinyl, 1-piperidinyl and 1-pyrrolidinyl is unsubstituted or carries 1,2,3 or 4 radicals R2dSaid R is2dIs selected from C1-C4Alkyl and fluoro C1-C4-alkyl, preferably selected from methyl, ethyl and trifluoromethyl. Specifically, R2aAnd R2bTogether with the nitrogen atom to which they are bound form an (unsubstituted) 4-morpholinyl group.
Preferred compounds of the invention are compounds of formulae I, I.A, I.B, I.C and I.DLikewise, compounds of the formulae I ', I.A ', I.B ', I.C ' and I.D ', their N-oxides and their salts, where R is2cIs hydrogen or C1-C4-alkyl, and wherein R2cEspecially hydrogen.
In formulae I, I.A, I.B, I.C, I.D, I ', I.A ', I.B ', I.C ' and I.D ', R2a、R2bAnd R2cThe combinations of (a) and (b) are in particular as follows:
R2ais selected from C1-C4Alkyl radical, C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkyl-methyl, fluoro C1-C4Alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1,2,3 or 4 identical or different radicals R21Is substituted, and wherein R21Preferably selected from halogen, CN, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-haloalkoxy, and wherein R21In particular from halogen, C1-C4-alkyl, fluoro C1-C2Alkyl radical, C1-C4Alkoxy and fluoro C1-C2-alkoxy, in particular selected from halogen, methyl and methoxy; hydrogen, C1-C4Alkyl radical, C3-C6-cycloalkyl, C3-C6-cycloalkyl-methyl and fluoro C1-C4-an alkyl group,
R2amore particularly from C1-C4Alkyl radical, C3-C7-cycloalkyl, fluoro C1-C4Alkyl radical, C1-C4Alkoxy and phenyl, where phenyl is unsubstituted or substituted by 1 or 2 radicals R21Substituted, said R21Are identical or different and are preferably selected from halogen, C1-C4-alkyl, fluoro C1-C2Alkyl radical, C1-C4Alkoxy and fluoro C1-C2Alkoxy, in particular selected from halogen, methyl and methoxy,
R2aeven more particularly from C1-C4-alkyl, fluoro C1-C2Alkyl radical, C3-C4-cycloalkyl and phenyl, said phenyl being unsubstituted or substituted by 1,2 or 3 substituents selected from halogen, C1-C4-alkyl, fluoro C1-C2Alkyl radical, C1-C4Alkoxy and fluoro C1-C2The radical R of an alkoxy group21And wherein phenyl is in particular unsubstituted or substituted by 1,2 or 3 radicals selected from the group consisting of halogen, methyl and methoxy,
R2ain particular from methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2-、CF3CH2-、CH3O-, 4-Cl-phenyl, 4-methoxyphenyl, 4-methylphenyl and 2, 6-dimethylphenyl;
R2bselected from hydrogen, C1-C4Alkyl radical, C3-C7-cycloalkyl and fluoro C1-C4Alkyl, in particular selected from hydrogen, C1-C4-alkyl, fluoro C1-C2-alkyl and C3-C4Cycloalkyl, in particular selected from hydrogen, methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2And CF3CH2-；
Or
R2aAnd R2bTogether with the nitrogen atom to which they are bonded, may form a 5-or 6-membered saturated or unsaturated heterocyclyl radical which may contain as ring members a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1,2,3 or 4 radicals R2dSaid group R2dAre identical or different and are selected in particular from ═ O, halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-haloalkoxy, and wherein R2aAnd R2bTogether with the nitrogen atom to which they are bonded form, in particular, 4-morpholinyl, 4-thiomorpholinyl, 1-piperidinyl and 1-pyrrolidinyl, where 4-morpholinyl, 4-thiomorpholinyl, 1-piperidinyl and 1-pyrrolidinyl areUnsubstituted or carrying 1,2,3 or 4 radicals R2dSaid R is2dIs selected from C1-C4Alkyl and fluoro C1-C4-alkyl, preferably selected from methyl, ethyl and trifluoromethyl.
R2cIs hydrogen or C1-C4-alkyl, and especially hydrogen.
More particularly, in formulas I, I.A, I.B, I.C, I.D, I ', I.A ', I.B ', I.C ' and I.D ', R2a、R2bAnd R2cThe combination of (a) and (b) is as follows:
R2ais selected from C1-C6Alkyl radical, C3-C6-cycloalkyl, C1-C4Haloalkyl and phenyl, wherein phenyl is unsubstituted or substituted by 1,2,3 or 4 identical or different C1-C4-alkyl substitution;
R2bselected from hydrogen, C1-C4-alkyl and C3-C6-a cycloalkyl group; or
R2aAnd R2bTogether with the nitrogen atom to which they are bound, form a 5-or 6-membered saturated heterocyclic group which may contain as ring members a further heteroatom selected from O, S and N and which is unsubstituted or carries 1,2,3 or 4 atoms selected from C1-C4Alkyl and fluoro C1-C4-radical R of an alkyl radical2d(ii) a And is
R2cIs hydrogen or C1-C4-alkyl, especially hydrogen.
Even more particularly, in formulas I, I.A, I.B, I.C, I.D, I ', I.A ', I.B ', I.C ' and I.D ', R2a、R2bAnd R2cThe combination of (a) and (b) is as follows:
R2ais selected from C1-C4Alkyl radical, C3-C6-cycloalkyl, fluoro C1-C4-alkyl and phenyl, said phenyl being unsubstituted or substituted with 1,2,3 or 4 methyl groups;
R2bselected from hydrogen, C1-C4-alkyl and C3-C6-a cycloalkyl group; or
R2aAnd R2bTogether with the nitrogen atom to which they are attached form a 4-morpholinyl ring; and is
R2cIs hydrogen or C1-C4-alkyl, especially hydrogen.
In particular, in formulae I, I.A, I.B, I.C, I.D, I ', I.A ', I.B ', I.C ' and I.D ', R2a、R2bAnd R2cThe combination of (a) and (b) is as follows:
R2ais selected from C1-C4Alkyl radical, C3-C4-cycloalkyl, fluoro C1-C2-alkyl and phenyl, said phenyl being unsubstituted or substituted with 1,2 or 3 methyl groups;
R2bselected from hydrogen, C1-C3-alkyl and C3-C4-a cycloalkyl group; or
R2aAnd R2bTogether with the nitrogen atom to which they are attached form a 4-morpholinyl ring; and is
R2cIs hydrogen or C1-C4-alkyl, especially hydrogen.
Preferred compounds of the invention are compounds of the formulae I, I.A, I.B, I.C and I.D, and also compounds of the formulae I ', I.A ', I.B ', I.C ' and I.D ', their N-oxides and their salts, where R is3Selected from hydrogen, cyano, halogen, nitro, C1-C6Alkyl radical, C1-C8-haloalkyl group, C1-C4-alkoxy, C1-C8-haloalkoxy-Z3、C2-C4-alkenyl, C2-C4-alkynyl, C2-C4Alkenyloxy, C2-C4-alkynyloxy and R3b-S(O)k-Z3Wherein the variables k, R3bAnd Z3Have one of the meanings defined herein; more preferably, R3Selected from halogen, nitro, C1-C6Alkyl radical, C1-C8-haloalkyl group, C1-C8-haloalkoxy-Z3And R3b-S(O)k-Z3Wherein the variables k, R3bAnd Z3Is provided with a bookOne of the meanings defined herein; even more preferably, R3Selected from halogen, nitro, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-haloalkoxy and R3b-S(O)kWherein the variables k and R3bHave one of the meanings defined herein.
At R3In the range of (1), R3bPreferably selected from C1-C6Alkyl radical, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4Alkyl radical, C1-C6-haloalkyl, phenyl and heterocyclyl, wherein heterocyclyl is a 5-or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1,2,3 or 4 heteroatoms selected from O, N and S as ring members, wherein phenyl and heterocyclyl are unsubstituted or are identical or different by 1,2,3 or 4 and are selected from halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-haloalkoxy group. More preferably, R3bIs selected from C1-C4Alkyl radical, C3-C7-cycloalkyl, C1-C4-haloalkyl and phenyl, wherein phenyl is unsubstituted or is identical or different by 1 or 2 and is selected from halogen and C1-C4-a radical substitution of alkoxy; here, R is particularly preferred3bIs methyl, ethyl, cyclopropyl (cPr), CF3、CHF2CH2-、CF3CH2-or CF3FF2-。
At R3In the range of (1), R3cPreferably selected from C1-C6Alkyl radical, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4Alkyl radical, C1-C6-haloalkyl group, C1-C4-alkoxy, C1-C6Haloalkoxy, phenyl and heterocyclyl, wherein heterocyclyl is a 5-or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1,2,3 or 4 heteroatoms selected from O, N and S as ringsWherein phenyl and heterocyclyl are unsubstituted or are identical or different by 1,2,3 or 4 and are selected from halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-haloalkoxy group. More preferably, R3cIs selected from C1-C4Alkyl radical, C1-C4-alkoxy, C3-C7-cycloalkyl, C1-C4-haloalkyl and phenyl, wherein phenyl is unsubstituted or is identical or different by 1 or 2 and is selected from halogen and C1-C4-a radical substitution of alkoxy.
At R3In the range of (1), R3dPreferably selected from C1-C6Alkyl radical, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4Alkyl radical, C1-C6-haloalkyl and phenyl, wherein phenyl is unsubstituted or is identical or different by 1,2,3 or 4 and is selected from halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-a group substitution of haloalkoxy; more preferably, R3dIs selected from C1-C4Alkyl radical, C3-C7-cycloalkyl and C1-C4-a haloalkyl group; particular preference is given to R3dIs methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2-or CF3CH2-。
At R3In the range of Z3In particular a covalent bond or a linear chain C1-C4-an alkanediyl group; preferably, Z3Is a covalent bond, -CH2-or-CH2CH2-。
In particular, R in the formulae I, I.A, I.B, I.C, I.D, I ', I.A', I.B ', I.C' and I.D3Selected from halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-haloalkoxy, C1-C4Alkylthio radical, C1-C4-haloalkylthio, C1-C4alkyl-S (O), C1-C4haloalkyl-S (O), C1-C4alkyl-S (O)2And C1-C4-haloalkyl-S (O)2。
More particularly, R in formulas I, I.A, I.B, I.C, I.D, I ', I.A', I.B ', I.C' and I.D3Selected from halogen, C1-C2Alkyl radical, C1-C2-haloalkyl group, C1-C2-haloalkoxy, C1-C2Alkylthio radical, C1-C2-haloalkylthio, C1-C2alkyl-S (O), C1-C2haloalkyl-S (O), C1-C2alkyl-S (O)2And C1-C2-haloalkyl-S (O)2In particular from Cl, F, Br, I, CH3、CF3、CHF2、OCF3、OCHF2、SCH3、SCF3、SCHF2、S(O)CH3、S(O)CH2CH3、S(O)2CH3And S (O)2CH2CH3More specifically R3Is Cl, Br, CF3、SCH3、S(O)CH3Or S (O)2CH3。
In an alternative more particular embodiment, R in formulas I, I.A, I.B, I.C, I.D, I ', I.A', I.B ', I.C' and I.D3Is halogen, in particular Cl or Br.
Preferred compounds of the invention are compounds of the formulae I, I.A, I.B, I.C and I.D, and also compounds of the formulae I ', I.A ', I.B ', I.C ' and I.D ', their N-oxides and their salts, where R is4Selected from hydrogen, cyano, halogen, nitro, CH3、CHF2And CF3In particular from hydrogen, cyano, chlorine, fluorine and CH3。
Even more preferred compounds of the invention are compounds of formula I, I.A, I.B, I.C, I.D, I ', I.A ', I.B ', I.C ' and I.D ', their N-oxides and their salts, wherein R is4Is hydrogen, chlorine or fluorine.
The most preferred compounds of the invention are of formula I, I.A, I.B, I.C, I.D, I ', I.A ', I.B ', I.C ' and I.D ', their N-oxides and their salts, wherein R is4Is hydrogen.
Preferred compounds of the invention are compounds of formula I, I.A, I.B, I.C, I.D, I ', I.A ', I.B ', I.C ' and I.D ', wherein R is R, N-oxides and salts thereof5Selected from hydrogen, CHF2、CF3And a halogen. More preferably, R5Is hydrogen or halogen, in particular hydrogen, chlorine or fluorine, especially hydrogen or fluorine. Very particularly, R5Is fluorine.
Preferred compounds of the invention are compounds of formula I, I.A, I.B, I.C, I.D, I ', I.A ', I.B ', I.C ' and I.D ', wherein R is R, N-oxides and salts thereof6a、R6b、R6c、R6dIndependently of one another, from C1-C6Alkyl radical, C1-C4-alkoxy-C1-C4-alkyl and phenyl. In particular, R6a、R6b、R6c、R6dIndependently of one another, from C1-C2Alkyl radical, C1-C2-alkoxy-C1-C2-alkyl, in particular selected from CH3、CH3CH2、CH3OCH2CH2And CH3OCH2More particularly from C1-C2-alkyl, and in particular independently of one another CH3。
Preferred compounds of the invention are compounds of formula I, I.A, I.B, I.C and I.D, wherein R is7Is hydrogen or C1-C4-alkyl, and wherein R7Especially hydrogen.
In the context of the present invention, the variable R11、R21、R22、R23、R24、R25、Z1、Z3、Z3a、Z4、Rb、R1b、R3b、R3c、R3d、R3e、R3f、R3g、R3h、R4b、R4c、R4d、R4e、R4f、R4g、R4h、Rk、RzN and k, independently of one another, preferably have one of the following meanings:
in particular, R11、R21Independently of one another, from halogen, C1-C4Alkyl radical, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C4-haloalkyl group, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4Alkyl radical, C1-C4-alkylthio-C1-C4Alkyl radical, C1-C4-alkoxy-C1-C4-alkoxy and C1-C6-haloalkyloxy, more preferably selected from halogen, C1-C4Alkyl radical, C3-C6-cycloalkyl, C1-C4-haloalkyl and C1-C4-alkoxy groups.
More preferably R11、R21Independently of one another, from halogen, C1-C4Alkyl radical, C3-C6-cycloalkyl, C1-C4-haloalkyl group, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4Alkyl radical, C1-C4-alkylthio-C1-C4-alkyl and C1-C4-alkoxy-C1-C4-an alkoxy group; in particular from halogen, C1-C4Alkyl radical, C1-C4-alkoxy, C1-C4-haloalkyl group, C1-C4-alkoxy-C1-C4-alkyl and C1-C4-alkoxy-C1-C4-an alkoxy group; and is specifically selected from Cl, F, Br, methyl, ethyl, methoxy and trifluoromethyl.
In particular, R22Selected from hydrogen, C1-C6Alkyl radical, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C6-haloalkyl group, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl, benzyl and heterocyclyl, wherein heterocyclyl is a 5-or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which comprises 1,2 or 3 heteroatoms selected from O, N and S as ring members, wherein the rings of phenyl, benzyl and heterocyclyl are unsubstituted or are substituted by 1,2 or 3 identical or different and are selected from halogen, C1-C4Alkyl radical, C1-C4-haloalkyl and C1-C4-a radical substitution of alkoxy.
More preferably R22Selected from hydrogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, phenyl and heterocyclyl, wherein heterocyclyl is a 5-or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle comprising 1,2 or 3 heteroatoms selected from O, N and S as ring members.
In particular, R22Selected from hydrogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C2-C4-alkenyl, C2-C4-haloalkenyl, C3-C6Cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5-or 6-membered aromatic heterocyclyl having 1 or 2 nitrogen atoms as ring members.
In particular, R23Selected from hydrogen, C1-C6Alkyl radical, C1-C6-haloalkyl group, C2-C6-alkenyl, C3-C6-cycloalkyl and phenyl. More preferably R23Selected from hydrogen, C1-C4Alkyl radical, C1-C4-haloalkyl and C3-C6-a cycloalkyl group; and in particular R23Selected from hydrogen, C1-C3-alkyl and C1-C3-haloalkyl.
R24In particular from C1-C6Alkyl radical, C1-C6-haloalkyl group, C2-C6-alkenyl, C3-C6-cycloalkyl and phenyl.
More preferably R24In particular from C1-C4Alkyl radical, C1-C4-haloalkyl and C3-C6-a cycloalkyl group; and in particular R23Is selected from C1-C3-alkyl and C1-C3-haloalkyl.
R25In particular from C1-C6Alkyl radical, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C6-haloalkyl group, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl, benzyl and heterocyclyl, wherein heterocyclyl is a 5-or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which comprises 1,2 or 3 heteroatoms selected from O, N and S as ring members, wherein the rings of phenyl, benzyl and heterocyclyl are unsubstituted or are substituted by 1,2 or 3 identical or different and are selected from halogen, C1-C4Alkyl radical, C1-C4-haloalkyl and C1-C4-a radical substitution of alkoxy.
More preferably R25Is selected from C1-C4Alkyl radical, C1-C4-haloalkyl group, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, phenyl and heterocyclyl, wherein heterocyclyl is a 5-or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle comprising 1,2 or 3 heteroatoms selected from O, N and S as ring members.
In particular, R25Is selected from C1-C4Alkyl radical, C1-C4-haloalkyl group, C2-C4-alkenyl, C2-C4-haloalkenyl, C3-C6Cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5-or 6-membered aromatic heterocyclyl having 1 or 2 nitrogen atoms as ring members.
Z1、Z3、Z4Independently of one another, are chosen in particular from covalent bonds, methyldi radicals and ethanediyl radicals, and in particular covalent bonds.
Z3aIn particular from covalent bonds, C1-C2Alkanediyl, O-C1-C2Alkanediyl, C1-C2alkanediyl-O and C1-C2-alkanediyl-O-C1-C2-an alkanediyl group; more preferably selected from the group consisting of covalent bonds, methanediyl, ethanediyl, O-methanediyl, O-ethanediyl, methanediyl-O and ethanediyl-O; and in particular selected from covalent bonds, methyldi groups and ethanediyl groups.
Rb、R1b、R3b、R4bIndependently of one another, in particular from C1-C6Alkyl radical, C3-C7-cycloalkyl, C1-C6-haloalkyl group, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl and heterocyclyl, wherein heterocyclyl is a 5-or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which comprises 1,2 or 3 heteroatoms selected from O, N and S as ring members, wherein phenyl and heterocyclyl are unsubstituted or are identical or different by 1,2 or 3 and are selected from halogen, C1-C4Alkyl radical, C1-C2-haloalkyl and C1-C2-a radical substitution of alkoxy.
More preferably Rb、R1b、R3b、R4bIndependently of one another, from C1-C4Alkyl radical, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-haloalkyl group, C2-C4-haloalkenyl, C2-C4-haloSubstituted alkynyl, C3-C6-cycloalkyl, phenyl and heterocyclyl, wherein heterocyclyl is a 5-or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle comprising 1,2 or 3 heteroatoms selected from O, N and S as ring members.
In particular, Rb、R1b、R3b、R4bIndependently of one another, from C1-C4Alkyl radical, C1-C4-haloalkyl group, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C3-C6Cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5-or 6-membered aromatic heterocyclyl having 1 or 2 nitrogen atoms as ring members.
R3c、R4c、RkIndependently of one another, in particular from hydrogen, C1-C6Alkyl radical, C3-C7-cycloalkyl, which is unsubstituted or partially or fully halogenated; c1-C6-haloalkyl group, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl, benzyl and heterocyclyl, wherein heterocyclyl is a 5-or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which comprises 1,2 or 3 heteroatoms selected from O, N and S as ring members, wherein phenyl, benzyl and heterocyclyl are unsubstituted or are identical or different by 1,2 or 3 and are selected from halogen, C1-C4Alkyl radical, C1-C4-haloalkyl and C1-C4-a radical substitution of alkoxy.
More preferably R3c、R4c、RkIndependently of one another, from hydrogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C3-C6Cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5-or 6-membered unitA cyclic saturated, partially unsaturated or aromatic heterocycle comprising 1,2 or 3 heteroatoms selected from O, N and S as ring members.
In particular, R3c、R4c、RkIndependently of one another, from hydrogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C2-C4-alkenyl, C2-C4-haloalkenyl, C3-C6Cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5-or 6-membered aromatic heterocyclyl having 1 or 2 nitrogen atoms as ring members.
R3d、R4dIndependently of one another, in particular from C1-C6Alkyl radical, C3-C7-cycloalkyl, which is unsubstituted or partially or fully halogenated; c1-C6-haloalkyl group, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl and benzyl.
More preferably R3d、R4dIndependently of one another, from C1-C6Alkyl radical, C1-C6-haloalkyl group, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C1-C4-alkoxy-C1-C4-alkyl and C3-C7Cycloalkyl, unsubstituted or partially or fully halogenated, in particular selected from C1-C4Alkyl radical, C1-C4-haloalkyl group, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C3-C6-a cycloalkyl group.
R3e、R3f、R4e、R4fIndependently of one another, in particular from hydrogen, C1-C6Alkyl radical, C3-C7Cycloalkyl which is unsubstituted or partially or fully halogenGeneration; c1-C6-haloalkyl group, C2-C6-alkenyl, C2-C6-haloalkenyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl and benzyl, wherein phenyl and benzyl are unsubstituted or substituted by 1,2 or 3 groups which are the same or different and selected from halogen, C1-C4Alkyl radical, C1-C4-haloalkyl and C1-C4-alkoxy, or R3eAnd R3fTogether with the nitrogen atom to which they are bonded, may form a 5-, 6-or 7-membered saturated or unsaturated heterocyclyl radical which may contain as ring members a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1,2,3 or 4 identical or different and selected from halogen, C1-C4Alkyl radical, C1-C4-haloalkyl and C1-C4-a radical of an alkoxy group.
More preferably R3e、R3f、R4e、R4fIndependently of one another, from hydrogen, C1-C6Alkyl radical, C1-C6-haloalkyl and benzyl, or R3eAnd R3fTogether with the nitrogen atom to which they are bonded, may form a 5-or 6-membered saturated or unsaturated heterocyclyl radical which may contain as ring members a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1,2 or 3 identical or different radicals selected from halogen, C1-C4-alkyl and C1-C4-a haloalkyl group.
In particular, R3e、R3f、R4e、R4fIndependently of one another, from hydrogen and C1-C4-alkyl, or R3eAnd R3fTogether with the nitrogen atom to which they are attached, may form a 5-or 6-membered saturated heterocyclic group, which may contain as ring members a further heteroatom selected from O, S and N, and which is unsubstituted or may carry 1,2 or 3 methyl groups.
R3g、R4gIndependently of one another, in particular from hydrogen, C1-C6Alkyl radical, C3-C7-cycloalkyl, which is unsubstitutedOr partially or fully halogenated; c1-C6-haloalkyl group, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl and benzyl.
More preferably R3g、R4gIndependently of one another, in particular from hydrogen, C1-C6Alkyl radical, C1-C6-haloalkyl group, C2-C6-alkenyl, C2-C6-haloalkenyl, benzyl, C1-C4-alkoxy-C1-C4-alkyl and C3-C7Cycloalkyl, unsubstituted or partially or fully halogenated, in particular selected from hydrogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C2-C4-alkenyl, C2-C4-haloalkenyl, benzyl and C3-C6-a cycloalkyl group.
R3h、R4hIndependently of one another, in particular from hydrogen, C1-C6Alkyl radical, C3-C7-cycloalkyl, which is unsubstituted or partially or fully halogenated; c1-C6-haloalkyl group, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl, benzyl and the group C (═ O) -RkWherein R iskIs H, C1-C4Alkyl radical, C1-C4-haloalkyl or phenyl.
More preferably R3h、R4hIndependently of one another, from hydrogen, C1-C6Alkyl radical, C1-C6-haloalkyl group, C2-C6-alkenyl, C2-C6-haloalkenyl, benzyl, C1-C4-alkoxy-C1-C4-alkyl radicalAnd C3-C7Cycloalkyl, unsubstituted or partially or fully halogenated, and in particular selected from hydrogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C2-C4-alkenyl, C2-C4-haloalkenyl, benzyl and C3-C6-a cycloalkyl group; or
R3gAnd R3hOr R4gAnd R4hTogether with the nitrogen atom to which they are attached, there may also be formed, in particular, a 5-, 6-or 7-membered saturated or unsaturated heterocyclyl radical which may contain as ring members a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1,2,3 or 4 identical or different and selected from ═ O, halogen, C1-C4-alkyl and C1-C4-haloalkyl and C1-C4-a group of alkoxy groups; more preferably R3gAnd R3hOr R4gAnd R4hTogether with the nitrogen atom to which they are bonded, may form a 5-or 6-membered saturated or unsaturated heterocyclyl radical which may contain as ring members a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1,2 or 3 identical or different radicals selected from halogen, C1-C4-alkyl and C1-C4-a group of haloalkyl groups; and in particular R3gAnd R3hOr R4gAnd R4hTogether with the nitrogen atom to which they are attached, may form a 5-or 6-membered saturated heterocyclic group, which may contain as ring members a further heteroatom selected from O, S and N, and which is unsubstituted or may carry 1,2 or 3 methyl groups.
RzIs selected from C1-C6Alkyl radical, C1-C6-haloalkyl group, C3-C7-cycloalkyl, C1-C6-alkoxy, C2-C6Alkenyl, phenyl, benzyl, heterocyclyl and heterocyclylmethyl, where heterocyclyl in the last two mentioned radicals is a 5-or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which comprises 1,2 or 3 heteroatoms from the group consisting of O, N and S as ring members, wherein phenyl, benzyl and heterocyclyl are unsubstituted or are identical by 1,2,3 or 4Or different and selected from halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-haloalkoxy group.
Preferably, RzIs selected from C1-C6Alkyl radical, C1-C6-haloalkyl group, C1-C6-alkoxy, phenyl and benzyl, wherein phenyl and benzyl are unsubstituted or are identical or different by 1,2,3 or 4 and are selected from halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-haloalkoxy group.
More preferably, RzIs selected from C1-C4Alkyl radical, C1-C3-haloalkyl group, C1-C4-alkoxy, phenyl and benzyl, wherein phenyl and benzyl are unsubstituted or are identical or different by 1 or 2 and are selected from halogen, C1-C4-alkyl and C1-C4-substituted with a haloalkyl group; and in particular RzIs C1-C3Alkyl radical, C1-C3-haloalkyl or C1-C4-alkoxy groups.
The variable n is in particular 0 or 2, independently of its occurrence.
The variable k is, independently of its occurrence, in particular 0 or 2, in particular 2.
Particularly preferred are compounds of formula I, I.A, I.B, I.C, I.D, I ', I.A ', I.B ', I.C ' and I.D ', wherein the variable R is1And R3Has the following meanings:
R1selected from halogen, nitro, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkoxy-C1-C4Alkyl radical, C1-C4Alkylthio radical, C1-C4-haloalkylthio and C1-C4-alkanesAlkylsulfonyl, in particular selected from F, Cl, Br, I, nitro, CH3、CF3、OCH3、SCH3、SCF3、SO2CH3And CH2OCH2CH2OCH3More particularly from F, Cl, Br, I, nitro, CH3、CF3、OCH3、SCH3And SO2CH3Even more particularly from Cl, Br, CH3、CF3And OCH3In particular from Cl, CH3And OCH3In particular R1Is Cl or CH3(ii) a And is
R3Selected from halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-haloalkoxy, C1-C4Alkylthio radical, C1-C4-haloalkylthio, C1-C4alkyl-S (O), C1-C4haloalkyl-S (O), C1-C4alkyl-S (O)2And C1-C4-haloalkyl-S (O)2More particularly from halogen, C1-C2Alkyl radical, C1-C2-haloalkyl group, C1-C2-haloalkoxy, C1-C2Alkylthio radical, C1-C2-haloalkylthio, C1-C2alkyl-S (O), C1-C2haloalkyl-S (O), C1-C2alkyl-S (O)2And C1-C2-haloalkyl-S (O)2In particular from Cl, F, Br, I, CH3、CF3、CHF2、OCF3、OCHF2、SCH3、SCF3、SCHF2、S(O)CH3、S(O)CH2CH3、S(O)2CH3And S (O)2CH2CH3More specifically R3Is Cl, Br, CF3、SCH3、S(O)CH3Or S (O)2CH3。
In particular, the conversion to the formulae I, I.A, I.B, I.C, I.D, I ', I.A', I.B ', I.C' and I.DIn the compound, the variable R1And R3Has the following meanings:
R1selected from Cl, CH3And OCH3In particular from Cl or CH3(ii) a And is
R3Is halogen; specifically Cl or Br.
Particularly preferred groups 1 of the compounds of the invention are compounds of the formulae I, I.A, I.B, I.C, I.D, I ', I.A ', I.B ', I.C ' and I.D ', their N-oxides and their salts, where the variable R is4And R5Has the following meanings:
R4is hydrogen, chlorine or fluorine; in particular hydrogen;
R5other than hydrogen, in particular selected from halogen, CHF2And CF3(ii) a And is in particular selected from chlorine and fluorine, in particular fluorine.
Further particularly preferred groups 2 of the compounds of the invention are compounds of the formulae I, I.A, I.B, I.C, I.D, I ', I.A ', I.B ', I.C ' and I.D ', their N-oxides and their salts, where the variable R is4And R5Has the following meanings:
R4is chlorine or fluorine;
r5 is hydrogen.
Further particularly preferred groups 3 of the compounds of the invention are compounds of the formulae I, I.A, I.B, I.C, I.D, I ', I.A ', I.B ', I.C ' and I.D ', their N-oxides and their salts, where the variable R is4And R5Are all hydrogen.
Among the compounds of groups 1,2 and 3, preferred are those wherein Q is Q1Or Q2Or Q4And is specifically Q1。
Among the compounds of groups 1,2 and 3, preferred are those in which Z is2Is a covalent bond.
Of the compounds of groups 1,2 and 3, particularly preferred are those compounds in which Q is Q1Or Q2Or Q4And is specifically Q1And Z is2Is a covalent bond.
Combinations in 1,2 and 3Of these, preferred are those compounds in which Q is Q1Or Q2Or Q4And is specifically Q1，Z2Is a covalent bond, and wherein R1And R3The combination of (a) and (b) is as follows:
R1selected from halogen, nitro, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkoxy-C1-C4Alkyl radical, C1-C4Alkylthio radical, C1-C4-haloalkylthio and C1-C4Alkylsulfonyl, in particular selected from F, Cl, Br, I, nitro, CH3、CF3、OCH3、SCH3、SCF3、SO2CH3And CH2OCH2CH2OCH3More particularly from F, Cl, Br, I, nitro, CH3、CF3、OCH3、SCH3And SO2CH3Even more particularly from Cl, Br, CH3、CF3And OCH3In particular from Cl, CH3And OCH3In particular R1Is Cl or CH3(ii) a And is
R3Selected from halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-haloalkoxy, C1-C4Alkylthio radical, C1-C4-haloalkylthio, C1-C4alkyl-S (O), C1-C4haloalkyl-S (O), C1-C4alkyl-S (O)2And C1-C4-haloalkyl-S (O)2More particularly from halogen, C1-C2Alkyl radical, C1-C2-haloalkyl group, C1-C2-haloalkoxy, C1-C2Alkylthio radical, C1-C2-haloalkylthio, C1-C2alkyl-S (O), C1-C2haloalkyl-S (O), C1-C2alkyl-S (O)2And C1-C2-haloalkyl-S (O)2In particular from Cl, F, Br, I, CH3、CF3、CHF2、OCF3、OCHF2、SCH3、SCF3、SCHF2、S(O)CH3、S(O)CH2CH3、S(O)2CH3And S (O)2CH2CH3More specifically R3Is Cl, Br, CF3、SCH3、S(O)CH3Or S (O)2CH3。
Among the compounds of groups 1,2 and 3, more preferred are those wherein Q is Q1Or Q2Or Q4And is specifically Q1，Z2Is a covalent bond, and wherein R1And R3The combination of (a) and (b) is as follows:
R1selected from Cl, CH3And OCH3In particular from Cl or CH3(ii) a And is
R3Is halogen; specifically Cl or Br.
A particularly preferred group 1a of the compounds of the invention are the compounds of the formulae I, I.A, I.B, I.C, I.D, I ', I.A ', I.B ', I.C ' and I.D ', their N-oxides and their salts, where the variable R is1、R3、R4、R6a、R6b、R6c、R6dAnd R7Has the following meanings:
R1selected from halogen, nitro, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkoxy-C1-C4Alkyl radical, C1-C4Alkylthio radical, C1-C4-haloalkylthio and C1-C4Alkylsulfonyl, in particular selected from F, Cl, Br, I, nitro, CH3、CF3、OCH3、SCH3、SCF3、SO2CH3And CH2OCH2CH2OCH3More specifically selected from F, Cl, Br, I,Nitro group, CH3、CF3、OCH3、SCH3And SO2CH3Even more particularly from Cl, Br, CH3、CF3And OCH3In particular from Cl, CH3And OCH3In particular R1Is Cl or CH3；
R3Selected from halogen, nitro, C1-C2Alkyl radical, C1-C2-haloalkyl group, C1-C2-haloalkoxy, C1-C2Alkylthio radical, C1-C2-haloalkylthio, C1-C2alkyl-S (O), C1-C2haloalkyl-S (O), C1-C2alkyl-S (O)2And C1-C2-haloalkyl-S (O)2And wherein R is3In particular from Cl, Br, CF3、SCH3、S(O)CH3And S (O)2CH3；
R4Is hydrogen, chlorine or fluorine; in particular hydrogen;
R5selected from halogen, CHF2And CF3(ii) a And in particular from chlorine and fluorine;
R6a、R6b、R6c、R6dindependently of one another, from CH3、CH3CH2、CH3OCH2CH2And CH3OCH2(ii) a And in particular from CH3And CH3CH2(ii) a And is
R7Is hydrogen.
Another particularly preferred group 2a of the compounds of the invention are the compounds of the formulae I, I.A, I.B, I.C, I.D, I ', I.A ', I.B ', I.C ' and I.D ', their N-oxides and their salts, where Q is Q1、Q2、Q3Or Q4And the variable R1、R3、R4、R6a、R6b、R6c、R6dAnd R7Has the following meanings:
R1selected from halogen, nitro, C1-C4-alkanesBase, C1-C4-haloalkyl group, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkoxy-C1-C4Alkyl radical, C1-C4Alkylthio radical, C1-C4-haloalkylthio and C1-C4Alkylsulfonyl, in particular selected from F, Cl, Br, I, nitro, CH3、CF3、OCH3、SCH3、SCF3、SO2CH3And CH2OCH2CH2OCH3More particularly from F, Cl, Br, I, nitro, CH3、CF3、OCH3、SCH3And SO2CH3Even more particularly from Cl, Br, CH3、CF3And OCH3In particular from Cl, CH3And OCH3In particular R1Is Cl or CH3；
R3Selected from halogen, nitro, C1-C2Alkyl radical, C1-C2-haloalkyl group, C1-C2-haloalkoxy, C1-C2Alkylthio radical, C1-C2-haloalkylthio, C1-C2alkyl-S (O), C1-C2haloalkyl-S (O), C1-C2alkyl-S (O)2And C1-C2-haloalkyl-S (O)2And wherein R is3In particular from Cl, Br, CF3、SCH3、S(O)CH3And S (O)2CH3；
R4Is chlorine or fluorine;
R5is hydrogen;
R6a、R6b、R6c、R6dindependently of one another, from CH3、CH3CH2、CH3OCH2CH2And CH3OCH2(ii) a And in particular from CH3And CH3CH2(ii) a And is
R7Is hydrogen.
Further particularly preferred groups 3a of the compounds of the invention are compounds of the formulae I, I.A, I.B, I.C, I.D, I ', I.A ', I.B ', I.C ' and I.D ', their N-oxides and their salts, where Q is Q1、Q2、Q3Or Q4And the variable R1、R3、R4、R6a、R6b、R6c、R6dAnd R7Has the following meanings:
R1selected from halogen, nitro, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkoxy-C1-C4Alkyl radical, C1-C4Alkylthio radical, C1-C4-haloalkylthio and C1-C4Alkylsulfonyl, in particular selected from F, Cl, Br, I, nitro, CH3、CF3、OCH3、SCH3、SCF3、SO2CH3And CH2OCH2CH2OCH3More particularly from F, Cl, Br, I, nitro, CH3、CF3、OCH3、SCH3And SO2CH3Even more particularly from Cl, Br, CH3、CF3And OCH3In particular from Cl, CH3And OCH3In particular R1Is Cl or CH3；
R3Selected from halogen, nitro, C1-C2Alkyl radical, C1-C2-haloalkyl group, C1-C2-haloalkoxy, C1-C2Alkylthio radical, C1-C2-haloalkylthio, C1-C2alkyl-S (O), C1-C2haloalkyl-S (O), C1-C2alkyl-S (O)2And C1-C2-haloalkyl-S (O)2And wherein R is3In particular from Cl, Br, CF3、SCH3、S(O)CH3And S (O)2CH3；
R4Is hydrogen;
R5is hydrogen;
R6a、R6b、R6c、R6dindependently of one another, from CH3、CH3CH2、CH3OCH2CH2And CH3OCH2(ii) a And in particular from CH3And CH3CH2(ii) a And is
R7Is hydrogen.
Of the compounds of groups 1a, 2a and 3a, preference is given to those compounds in which Q is Q1Or Q2Or Q4In particular Q1。
Of the compounds of groups 1a, 2a and 3a, preference is given to those compounds in which Z is2Is a covalent bond.
Of the compounds of groups 1a, 2a and 3a, particular preference is given to those compounds in which Q is Q1Or Q2Or Q4In particular Q1And Z is2Is a covalent bond.
Even more preferred groups 1b of the compounds of the invention are compounds of the formulae I, I.A, I.B, I.C, I.D, I ', I.A ', I.B ', I.C ' and I.D ', their N-oxides and their salts, wherein the variable R is1、R2a、R2b、R2c、R3、R4、R6a、R6b、R6c、R6dAnd R7Has the following meanings:
R1selected from halogen, nitro, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkoxy-C1-C4Alkyl radical, C1-C4Alkylthio radical, C1-C4-haloalkylthio and C1-C4Alkylsulfonyl, in particular selected from F, Cl, Br, I, nitro, CH3、CF3、OCH3、SCH3、SCF3、SO2CH3And CH2OCH2CH2OCH3More particularly from F, Cl, Br, I, nitro, CH3、CF3、OCH3、SCH3And SO2CH3Even more particularly from Cl, Br, CH3、CF3And OCH3In particular from Cl, CH3And OCH3In particular R1Is Cl or CH3；
R2aIs selected from C1-C4Alkyl radical, C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkyl-methyl, fluoro C1-C4Alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1,2,3 or 4 identical or different radicals R21Is substituted, and wherein R21Preferably selected from halogen, CN, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-haloalkoxy, and wherein R21In particular from halogen, C1-C4-alkyl, fluoro C1-C2Alkyl radical, C1-C4Alkoxy and fluoro C1-C2-alkoxy, in particular selected from halogen, methyl and methoxy; hydrogen, C1-C4Alkyl radical, C3-C6-cycloalkyl, C3-C6-cycloalkyl-methyl and fluoro C1-C4-an alkyl group,
R2amore particularly from C1-C4Alkyl radical, C3-C7-cycloalkyl, fluoro C1-C4Alkyl radical, C1-C4Alkoxy and phenyl, where phenyl is unsubstituted or substituted by 1 or 2 radicals R21Substituted, said R21Are identical or different and are preferably selected from halogen, C1-C4-alkyl, fluoro C1-C2Alkyl radical, C1-C4Alkoxy and fluoro C1-C2Alkoxy, in particular selected from halogen, methyl and methoxy,
R2aeven more particularlyAre selected from C1-C4-alkyl, fluoro C1-C2Alkyl radical, C3-C4-cycloalkyl and phenyl, said phenyl being unsubstituted or substituted by 1,2 or 3 substituents selected from halogen, C1-C4-alkyl, fluoro C1-C2Alkyl radical, C1-C4Alkoxy and fluoro C1-C2The radical R of an alkoxy group21And wherein phenyl is in particular unsubstituted or substituted by 1,2 or 3 radicals selected from the group consisting of halogen, methyl and methoxy,
R2ain particular from methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2-、CF3CH2-、CH3O-, 4-Cl-phenyl, 4-methoxyphenyl, 4-methylphenyl and 2, 6-dimethylphenyl;
R2bselected from hydrogen, C1-C4Alkyl radical, C3-C7-cycloalkyl and fluoro C1-C4Alkyl, in particular selected from hydrogen, C1-C4-alkyl, fluoro C1-C2-alkyl and C3-C4Cycloalkyl, in particular selected from hydrogen, methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2And CF3CH2-；
Or
R2aAnd R2bTogether with the nitrogen atom to which they are bonded, may form a 5-or 6-membered saturated or unsaturated heterocyclyl radical which may contain as ring members a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1,2,3 or 4 radicals R2dSaid group R2dAre identical or different and are selected in particular from ═ O, halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-haloalkoxy, and wherein R2aAnd R2bTogether with the nitrogen atom to which they are bonded form, in particular, 4-morpholinyl, 4-thiomorpholinyl, 1-piperidinyl and 1-pyrrolidinyl, where 4-morpholinyl, 4-thiomorpholinyl, 1-piperidinyl and 1-pyrrolidinyl is unsubstituted orWith 1,2,3 or 4 radicals R2dSaid R is2dIs selected from C1-C4Alkyl and fluoro C1-C4-an alkyl group, preferably selected from methyl, ethyl and trifluoromethyl;
R2cis hydrogen or C1-C4-alkyl, especially hydrogen;
R3selected from halogen, nitro, C1-C2Alkyl radical, C1-C2-haloalkyl group, C1-C2-haloalkoxy, C1-C2Alkylthio radical, C1-C2-haloalkylthio, C1-C2alkyl-S (O), C1-C2haloalkyl-S (O), C1-C2alkyl-S (O)2And C1-C2-haloalkyl-S (O)2And wherein R is3In particular from Cl, Br, CF3、SCH3、S(O)CH3And S (O)2CH3(ii) a And wherein R3Specifically Cl or Br;
R4is hydrogen, chlorine or fluorine; in particular hydrogen;
R5selected from halogen, CHF2And CF3(ii) a And in particular from chlorine and fluorine;
R6a、R6b、R6c、R6dindependently of one another, from CH3、CH3CH2、CH3OCH2CH2And CH3OCH2(ii) a And in particular from CH3And CH3CH2(ii) a And is
R7Is hydrogen.
An equally more preferred group 2b of the compounds of the invention are the compounds of the formulae I, I.A, I.B, I.C, I.D, I ', I.A ', I.B ', I.C ' and I.D ', their N-oxides and their salts, where the variable R is1、R2a、R2b、R2c、R3、R4、R6a、R6b、R6c、R6dAnd R7Has the following meanings:
R1selected from halogen, nitro、C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkoxy-C1-C4Alkyl radical, C1-C4Alkylthio radical, C1-C4-haloalkylthio and C1-C4Alkylsulfonyl, in particular selected from F, Cl, Br, I, nitro, CH3、CF3、OCH3、SCH3、SCF3、SO2CH3And CH2OCH2CH2OCH3More particularly from F, Cl, Br, I, nitro, CH3、CF3、OCH3、SCH3And SO2CH3Even more particularly from Cl, Br, CH3、CF3And OCH3In particular from Cl, CH3And OCH3In particular R1Is Cl or CH3；
R2aIs selected from C1-C4Alkyl radical, C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkyl-methyl, fluoro C1-C4Alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1,2,3 or 4 identical or different radicals R21Is substituted, and wherein R21Preferably selected from halogen, CN, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-haloalkoxy, and wherein R21In particular from halogen, C1-C4-alkyl, fluoro C1-C2Alkyl radical, C1-C4Alkoxy and fluoro C1-C2-alkoxy, in particular selected from halogen, methyl and methoxy; hydrogen, C1-C4Alkyl radical, C3-C6-cycloalkyl, C3-C6-cycloalkyl-methyl and fluoro C1-C4-an alkyl group,
R2amore particularly from C1-C4-alkanesBase, C3-C7-cycloalkyl, fluoro C1-C4Alkyl radical, C1-C4Alkoxy and phenyl, where phenyl is unsubstituted or substituted by 1 or 2 radicals R21Substituted, said R21Are identical or different and are preferably selected from halogen, C1-C4-alkyl, fluoro C1-C2Alkyl radical, C1-C4Alkoxy and fluoro C1-C2Alkoxy, in particular selected from halogen, methyl and methoxy,
R2aeven more particularly from C1-C4-alkyl, fluoro C1-C2Alkyl radical, C3-C4-cycloalkyl and phenyl, said phenyl being unsubstituted or substituted by 1,2 or 3 substituents selected from halogen, C1-C4-alkyl, fluoro C1-C2Alkyl radical, C1-C4Alkoxy and fluoro C1-C2The radical R of an alkoxy group21And wherein phenyl is in particular unsubstituted or substituted by 1,2 or 3 radicals selected from the group consisting of halogen, methyl and methoxy,
R2ain particular from methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2-、CF3CH2-、CH3O-, 4-Cl-phenyl, 4-methoxyphenyl, 4-methylphenyl and 2, 6-dimethylphenyl;
R2bselected from hydrogen, C1-C4Alkyl radical, C3-C7-cycloalkyl and fluoro C1-C4Alkyl, in particular selected from hydrogen, C1-C4-alkyl, fluoro C1-C2-alkyl and C3-C4Cycloalkyl, in particular selected from hydrogen, methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2And CF3CH2-；
Or
R2aAnd R2bTogether with the nitrogen atom to which they are bound, may form a 5-or 6-membered saturated or unsaturated heterocyclyl group, which may contain as ring members a further heteroatom selected from O, S and N, and is unsubstitutedSubstituted or may carry 1,2,3 or 4 radicals R2dSaid group R2dAre identical or different and are selected in particular from ═ O, halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-haloalkoxy, and wherein R2aAnd R2bTogether with the nitrogen atom to which they are bonded form, in particular, 4-morpholinyl, 4-thiomorpholinyl, 1-piperidinyl and 1-pyrrolidinyl, where 4-morpholinyl, 4-thiomorpholinyl, 1-piperidinyl and 1-pyrrolidinyl is unsubstituted or carries 1,2,3 or 4 radicals R2dSaid R is2dIs selected from C1-C4Alkyl and fluoro C1-C4-an alkyl group, preferably selected from methyl, ethyl and trifluoromethyl;
R2cis hydrogen or C1-C4-alkyl, especially hydrogen;
R3selected from halogen, nitro, C1-C2Alkyl radical, C1-C2-haloalkyl group, C1-C2-haloalkoxy, C1-C2Alkylthio radical, C1-C2-haloalkylthio, C1-C2alkyl-S (O), C1-C2haloalkyl-S (O), C1-C2alkyl-S (O)2And C1-C2-haloalkyl-S (O)2And wherein R is3In particular from Cl, Br, CF3、SCH3、S(O)CH3And S (O)2CH3(ii) a And wherein R3Specifically Cl or Br;
R4is chlorine or fluorine;
r5 is hydrogen;
R6a、R6b、R6c、R6dindependently of one another, from CH3、CH3CH2、CH3OCH2CH2And CH3OCH2(ii) a And in particular from CH3And CH3CH2(ii) a And is
R7Is hydrogen.
Hair brushAlso more preferred group 3b of the compounds of the invention are the compounds of formula I, I.A, I.B, I.C, I.D, I ', I.A ', I.B ', I.C ' and I.D ', their N-oxides and their salts, wherein the variable R1、R2a、R2b、R2c、R3、R4、R6a、R6b、R6c、R6dAnd R7Has the following meanings:
R1selected from halogen, nitro, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkoxy-C1-C4Alkyl radical, C1-C4Alkylthio radical, C1-C4-haloalkylthio and C1-C4Alkylsulfonyl, in particular selected from F, Cl, Br, I, nitro, CH3、CF3、OCH3、SCH3、SCF3、SO2CH3And CH2OCH2CH2OCH3More particularly from F, Cl, Br, I, nitro, CH3、CF3、OCH3、SCH3And SO2CH3Even more particularly from Cl, Br, CH3、CF3And OCH3In particular from Cl, CH3And OCH3In particular R1Is Cl or CH3；
R2aIs selected from C1-C4Alkyl radical, C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkyl-methyl, fluoro C1-C4Alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1,2,3 or 4 identical or different radicals R21Is substituted, and wherein R21Preferably selected from halogen, CN, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-haloalkoxy, and wherein R21In particular from halogen, C1-C4-alkyl, fluoroGeneration C1-C2Alkyl radical, C1-C4Alkoxy and fluoro C1-C2-alkoxy, in particular selected from halogen, methyl and methoxy; hydrogen, C1-C4Alkyl radical, C3-C6-cycloalkyl, C3-C6-cycloalkyl-methyl and fluoro C1-C4-an alkyl group,
R2amore particularly from C1-C4Alkyl radical, C3-C7-cycloalkyl, fluoro C1-C4Alkyl radical, C1-C4Alkoxy and phenyl, where phenyl is unsubstituted or substituted by 1 or 2 radicals R21Substituted, said R21Are identical or different and are preferably selected from halogen, C1-C4-alkyl, fluoro C1-C2Alkyl radical, C1-C4Alkoxy and fluoro C1-C2Alkoxy, in particular selected from halogen, methyl and methoxy,
R2aeven more particularly from C1-C4-alkyl, fluoro C1-C2Alkyl radical, C3-C4-cycloalkyl and phenyl, said phenyl being unsubstituted or substituted by 1,2 or 3 substituents selected from halogen, C1-C4-alkyl, fluoro C1-C2Alkyl radical, C1-C4Alkoxy and fluoro C1-C2The radical R of an alkoxy group21And wherein phenyl is in particular unsubstituted or substituted by 1,2 or 3 radicals selected from the group consisting of halogen, methyl and methoxy,
R2ain particular from methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2-、CF3CH2-、CH3O-, 4-Cl-phenyl, 4-methoxyphenyl, 4-methylphenyl and 2, 6-dimethylphenyl;
R2bselected from hydrogen, C1-C4Alkyl radical, C3-C7-cycloalkyl and fluoro C1-C4Alkyl, in particular selected from hydrogen, C1-C4-alkyl, fluoro C1-C2-alkyl and C3-C4Cycloalkyl, in particular selected from hydrogen, methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2And CF3CH2-；
Or
R2aAnd R2bTogether with the nitrogen atom to which they are bonded, may form a 5-or 6-membered saturated or unsaturated heterocyclyl radical which may contain as ring members a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1,2,3 or 4 radicals R2dSaid group R2dAre identical or different and are selected in particular from ═ O, halogen, C1-C4Alkyl radical, C1-C4-haloalkyl group, C1-C4-alkoxy and C1-C4-haloalkoxy, and wherein R2aAnd R2bTogether with the nitrogen atom to which they are bonded form, in particular, 4-morpholinyl, 4-thiomorpholinyl, 1-piperidinyl and 1-pyrrolidinyl, where 4-morpholinyl, 4-thiomorpholinyl, 1-piperidinyl and 1-pyrrolidinyl is unsubstituted or carries 1,2,3 or 4 radicals R2dSaid R is2dIs selected from C1-C4Alkyl and fluoro C1-C4-an alkyl group, preferably selected from methyl, ethyl and trifluoromethyl;
R2cis hydrogen or C1-C4-alkyl, especially hydrogen.
R3Selected from halogen, nitro, C1-C2Alkyl radical, C1-C2-haloalkyl group, C1-C2-haloalkoxy, C1-C2Alkylthio radical, C1-C2-haloalkylthio, C1-C2alkyl-S (O), C1-C2haloalkyl-S (O), C1-C2alkyl-S (O)2And C1-C2-haloalkyl-S (O)2And wherein R is3In particular from Cl, Br, CF3、SCH3、S(O)CH3And S (O)2CH3(ii) a And wherein R3Specifically Cl or Br;
R4is hydrogen;
R5is hydrogen;
R6a、R6b、R6c、R6dindependently of one another, from CH3、CH3CH2、CH3OCH2CH2And CH3OCH2(ii) a And in particular from CH3And CH3CH2(ii) a And is
R7Is hydrogen.
Of the compounds of groups 1b, 2b and 3b, preference is given to those compounds in which Q is Q1Or Q2Or Q4And is specifically Q1。
Of the compounds of groups 1b, 2b and 3b, preference is given to those compounds in which Z is2Is a covalent bond.
Of the compounds of groups 1b, 2b and 3b, particular preference is given to those compounds in which Q is Q1Or Q2Or Q4And is specifically Q1，Z2Is a covalent bond.
Of the compounds of groups 1b, 2b and 3b, particular preference is given to those compounds in which Q is Q1Or Q2Or Q4And is specifically Q1，Z2Is a covalent bond.
A very preferred group 1c of the compounds of the invention are the compounds of the formulae I.A ', I.B ' and I.D ', their N-oxides and their salts, where the variable R1、R2a、R2b、R2c、R3、R4、R6a、R6b、R6c、R6dAnd R7Has the following meanings:
R1is halogen, C1-C2-alkyl or C1-C2Alkoxy, such as Cl, CH3Or OCH3(ii) a In particular halogen or C1-C2Alkyl, in particular Cl or CH3；
R2aSelected from hydrogen, C1-C4Alkyl radical, C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkyl-methyl, fluoroC1-C4-alkyl, phenyl and benzyl, wherein phenyl and benzyl are unsubstituted or substituted by 1,2,3 or 4 groups selected from halogen, methyl and methoxy,
R2ain particular from C1-C4-alkyl radical, C1-C4-alkoxy, C3-C7-cycloalkyl, fluoro C1-C4-alkyl and phenyl, wherein phenyl is unsubstituted or substituted by 1,2 or 3 groups selected from halogen, methyl and methoxy, R2aEven more particularly from C1-C4-alkyl, fluoro C1-C2Alkyl radical, C3-C4-cycloalkyl and phenyl, said phenyl being unsubstituted or substituted by 1,2 or 3 groups selected from halogen, methyl and methoxy, in particular by 1,2 or 3 methyl groups; r2aIn particular from methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2-、CF3CH2-、CH3O-, 4-Cl-phenyl, 4-methoxyphenyl, 4-methylphenyl and 2, 6-dimethylphenyl;
R2bis selected from C1-C4Alkyl radical, C3-C6-cycloalkyl, C3-C6-cycloalkyl-methyl and fluoro C1-C4-an alkyl group; in particular from hydrogen, C1-C4-alkyl, fluoro C1-C2-alkyl and C3-C4Cycloalkyl, in particular selected from hydrogen, methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2And CF3CH2-；
Or
R2aAnd R2bTogether with the nitrogen atom to which they are bound form a 5-or 6-membered saturated heterocyclic group which may contain as ring members a further heteroatom selected from O, S and N, and wherein the heterocyclic group is selected from 4-morpholinyl, 4-thiomorpholinyl, 1-piperidinyl and 1-pyrrolidinyl, wherein 4-morpholinyl, 4-thiomorpholinyl, 1-piperidinyl and 1-pyrrolidinyl are unsubstituted or carry 1,2,3 or 4 substituents selected from C1-C4Alkyl and fluoro C1-C4-alkyl radicalGroup R of2dWherein R is2dIn particular from methyl and trifluoromethyl;
R2cselected from hydrogen and C1-C4-alkyl, especially hydrogen;
R3selected from halogen, C1-C2-alkyl, fluoro C1-C2Alkyl, S-C1-C2Alkyl, S (O) -C1-C2Alkyl, S (O)2-C1-C2Alkyl, S- (fluoro C)1-C2-alkyl), S (O) - (fluoro-C)1-C2Alkyl) and S (O)2- (fluoro C)1-C2-alkyl), and wherein R3In particular from Cl, Br, CF3、SCH3、S(O)CH3And S (O)2CH3；
R4Is hydrogen;
R5is fluorine;
R6a、R6bindependently of one another, from C1-C4-alkyl and C1-C4-alkoxy-C1-C4-an alkyl group;
R7as defined above, in particular hydrogen.
In a particular embodiment, in the compounds of formulae I, i.a, i.b., i.c, i.d, I ', i.a ', I.B ' and i.d
R1Is halogen, C1-C2-alkyl or C1-C2Alkoxy, especially Cl, CH3Or OCH3；
R2aIs selected from C1-C4Alkyl radical, C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkyl-methyl, fluoro C1-C4-alkyl, phenyl and benzyl, wherein phenyl and benzyl are unsubstituted or substituted with 1,2,3 or 4 groups selected from halogen, methyl and methoxy;
R2bselected from hydrogen, C1-C4Alkyl radical, C3-C6-cycloalkyl, C3-C6-cycloalkyl-methyl and fluoro C1-C4-an alkyl group; or
R2aAnd R2bTogether with the nitrogen atom to which they are bound form a 5-or 6-membered saturated heterocyclyl radical selected from the group consisting of 4-morpholinyl, 4-thiomorpholinyl, 1-piperidinyl and 1-pyrrolidinyl, where 4-morpholinyl, 4-thiomorpholinyl, 1-piperidinyl and 1-pyrrolidinyl is unsubstituted or carries 1,2,3 or 4 radicals R2dSaid R is2dIs selected from C1-C4Alkyl and fluoro C1-C4-an alkyl group;
R2cselected from hydrogen and C1-C4-an alkyl group;
R3selected from halogen, C1-C2-alkyl, fluoro C1-C2Alkyl, S-C1-C2Alkyl, S (O) -C1-C2Alkyl, S (O)2-C1-C2Alkyl, S- (fluoro C)1-C2-alkyl), S (O) - (fluoro-C)1-C2Alkyl) and S (O)2- (fluoro C)1-C2-an alkyl group);
R4is a hydrogen atom, and is,
R5is hydrogen or fluorine;
R6a、R6band R6dIndependently of one another select C1-C4-alkyl and C1-C4-alkoxy-C1-C4-an alkyl group; and is
R7Is hydrogen.
Among said compounds, the compounds of formula I are in particular those of formula I.A ', I.B ' or I.D ' (i.e. Z)2Is a covalent bond), in particular a compound of formula i.a'.
In a more particular embodiment, in the compounds of formulae I, i.a, i.b., i.c, i.d, I ', i.a ', I.B ' and i.d
R1Is halogen, C1-C2-alkyl or C1-C2Alkoxy, especially Cl, CH3Or OCH3；
R2aIs selected from C1-C4Alkyl radical, C3-C6-cycloalkyl, fluoro C1-C4-alkyl and phenyl, said phenyl being unsubstituted or substituted with 1,2,3 or 4 methyl groups;
R2bselected from hydrogen, C1-C4-alkyl and C3-C6-a cycloalkyl group; or
R2aAnd R2bTogether with the nitrogen atom to which they are attached form a 4-morpholinyl ring;
R2cis hydrogen;
R3is halogen;
R4is a hydrogen atom, and is,
R5is hydrogen or fluorine;
R6a、R6band R6dIndependently of one another is C1-C4-an alkyl group; and is
R7Is hydrogen.
Among said compounds, the compounds of formula I are in particular those of formula I.A ', I.B ' or I.D ' (i.e. Z)2Is a covalent bond), in particular a compound of formula i.a'.
In an even more particular embodiment, in the compounds of formula I, i.a, i.b., i.c, i.d, I ', i.a ', I.B ' and i.d
R1Is halogen, C1-C2-alkyl or C1-C2Alkoxy, especially Cl, CH3Or OCH3In particular Cl or CH3；
R2aIs selected from C1-C4Alkyl radical, C3-C4-cycloalkyl, fluoro C1-C2-alkyl and phenyl, said phenyl being unsubstituted or substituted with 1,2 or 3 methyl groups;
R2bselected from hydrogen, C1-C3-alkyl and C3-C4-a cycloalkyl group; or
R2aAnd R2bTogether with the nitrogen atom to which they are attached form a 4-morpholinyl ring;
R2cis hydrogen;
R3is halogen;
R4is a hydrogen atom, and is,
R5is hydrogen or fluorine;
R6a、R6band R6dIndependently of one another is C1-C2-an alkyl group; and is
R7Is hydrogen.
Among said compounds, the compounds of formula I are in particular compounds of formula i.a ', I.B' or i.d ', in particular compounds of formula i.a'.
Examples of preferred compounds are the individual compounds compiled in tables 1 to 48 below. Furthermore, the meanings of the individual variables mentioned in the following table are themselves particularly preferred embodiments of the substituents, independently of the combination in which they are present.
Compounds I.A'. I, wherein Q is Q1，R4Is hydrogen, R5Is hydrogen, R6aIs methyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs H:
TABLE 1 Compounds of the formula I.A '. I (I.A '. I.1-I.A '. I.1656), where for the compounds R1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compounds I.A'. II, in which Q is Q1，R4Is hydrogen, R5Is hydrogen, R6aIs ethyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs H:
TABLE 2 Compounds of the formula I.A '. II (I.A '. II.1-I.A '. II.1656), where R for the compounds1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
chemical combinationThe compound I.A'. III, wherein Q is Q1，R4Is hydrogen, R5Is hydrogen, R6aIs methyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs a methyl group:
TABLE 3 Compounds of the formula I.A '. III (I.A '. III.1-I.A '. III.1656), where for the compounds R1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compounds I.A'. IV, wherein Q is Q1，R4Is hydrogen, R5Is hydrogen, R6aIs ethyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs a methyl group:
TABLE 4 Compounds of the formula I.A '. IV (I.A '. IV.1-I.A '. IV.1656), where R for the compounds1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compounds I.A'. V, wherein Q is Q1，R4Is hydrogen, R5Is hydrogen, R6aIs methyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs ethyl:
TABLE 5 Compounds of the formula I.A '. V (I.A '. V.1-I.A '. V.1656), where for the compounds R1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compounds I.A'. VI in which Q is Q1，R4Is hydrogen, R5Is hydrogen, R6aIs ethyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs ethyl:
TABLE 6 Compounds of the formula I.A '. VI (I.A '. VI.1-I.A '. VI.1656), where for the compounds R1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compounds I.A'. VII in which Q is Q1，R4Is hydrogen, R5Is fluorine, R6aIs methyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs H:
TABLE 7 Compounds of the formula I.A '. VII (I.A '. VII.1-I.A '. VII.1656), where R for the compounds1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compounds I.A'. VIII, wherein Q is Q1，R4Is hydrogen, R5Is fluorine, R6aIs ethyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs H:
TABLE 8 Compounds of the formula I.A '. VIII (I.A '. VIII.1-I.A '. VIII.1656), where for the compounds R is1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compounds I.A'. IX, wherein Q is Q1，R4Is hydrogen, R5Is fluorine, R6aIs methyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs a methyl group:
TABLE 9 Compounds of the formula IA '. IX (I.A '. IX.1-I.A '. IX.1656), where for the compounds R1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compound i.a'. X wherein Q is Q1，R4Is hydrogen, R5Is fluorine, R6aIs ethyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs a methyl group:
TABLE 10 Compounds of the formula I.A '. X (I.A '. X.1-I.A '. X.1656), where for the compounds R1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compounds I.A'. XI, wherein Q is Q1，R4Is hydrogen, R5Is fluorine, R6aIs methyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs ethyl:
TABLE 11 Compounds of the formula I.A '. XI (I.A '. XI.1-I.A '. XI.1656), where for the compounds R is1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compounds I.A'. XII, in which Q is Q1，R4Is hydrogen, R5Is fluorine, R6aIs ethyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs ethyl:
TABLE 12 Compounds of the formula I.A '. XII (I.A '. XII.1-I.A '. XII.1656), where for the compounds R is1、R2a、
R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compound I.B'. I, wherein Q is Q2，R4Is hydrogen, R5Is hydrogen, R6bIs methyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs H:
TABLE 13 Compounds of formula I.B '. I (I.B '. I.1-I.B '. I.1656), wherein for compounds R is1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compound I.B'. II, wherein Q is Q2，R4Is hydrogen, R5Is hydrogen, R6bIs ethyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs H:
TABLE 14 Compounds of the formula I.B '. II (I.B '. II.1-I.B '. II.1656), where for the compounds R1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compound I.B'. III, wherein Q is Q2，R4Is hydrogen, R5Is hydrogen, R6bIs methyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs a methyl group:
TABLE 15 Compounds of the formula I.B '. III (I.B '. III.1-I.B '. III.1656), where for the compounds R1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compound I.B'. IV, wherein Q is Q2，R4Is hydrogen, R5Is hydrogen, R6bIs ethyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs a methyl group:
TABLE 16 Compounds of formula I.B '. IV (I.B '. IV.1-I.B '. IV.1656), where for compounds R is1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compound I.B'. V, wherein Q is Q2，R4Is hydrogen, R5Is hydrogen, R6bIs methyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs ethyl:
TABLE 17 Compounds of formula I.B '. V (I.B '. V.1-I.B '. V.1656), where for compounds R is1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compound I.B'. VI, wherein Q is Q2，R4Is hydrogen, R5Is hydrogen, R6bIs ethyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs ethyl:
table 18 compounds of formula I.B '. VI (I.B '. vi.1-I.B '. vi.1656), wherein for compounds R is1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compound I.B'. VII, wherein Q is Q2，R4Is hydrogen, R5Is fluorine, R6bIs methyl, R7Is hydrogen, Z2Is covalently boundA bond, and R2cIs H:
TABLE 19 Compounds of the formula I.B '. VII (I.B '. VII.1-I.B '. VII.1656), where for the compounds R is1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compound I.B'. VIII, wherein Q is Q2，R4Is hydrogen, R5Is fluorine, R6bIs ethyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs H:
TABLE 20 Compounds of formula I.B '. VIII (I.B '. VIII.1-I.B '. VIII.1656), where for compounds R is1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compound I.B'. IX, wherein Q is Q2，R4Is hydrogen, R5Is fluorine, R6bIs methyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs a methyl group:
table 21 compounds of formula I.B '. IX (I.B '. ix.1-I.B '. ix.1656), wherein for compounds R is1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compound I.B'. X, wherein Q is Q2，R4Is hydrogen, R5Is fluorine, R6bIs ethyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs a methyl group:
TABLE 22 Compounds of formula I.B '. X (I.B '. X.1-I.B '. X.1656), where for compounds R is1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compound I.B'. XI, wherein Q is Q2，R4Is hydrogen, R5Is fluorine, R6bIs methyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs ethyl:
TABLE 23 Compounds of formula I.B '. XI (I.B '. XI.1-I.B '. XI.1656), where for compounds R is1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compound I.B'. XII, wherein Q is Q2，R4Is hydrogen, R5Is fluorine, R6bIs ethyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs ethyl:
TABLE 24 Compounds of the formula I.B '. XII (I.B '. XII.1-I.B '. XII.1656), where for the compounds R is1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compounds I.C'. I, wherein Q is Q3，R4Is hydrogen, R5Is hydrogen, R6cIs methyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs H:
TABLE 25 Compounds of the formula I.C '. I (I.C '. I.1-I.C '. I.1656), where for the compounds R1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compounds I.C'. II in which Q is Q3，R4Is hydrogen, R5Is hydrogen, R6cIs ethyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs H:
TABLE 26 Compounds of the formula I.C '. II (I.C '. II.1-I.C '. II.1656), where for the compounds R1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compounds I.C'. III, where Q is Q3，R4Is hydrogen, R5Is hydrogen, R6cIs methyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs a methyl group:
TABLE 27 Compounds of the formula I.C '. III (I.C '. III.1-I.C '. III.1656), where for the compounds R1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compounds I.C'. IV, where Q is Q3，R4Is hydrogen, R5Is hydrogen, R6cIs ethyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs a methyl group:
TABLE 28 Compounds of the formula I.C '. IV (I.C '. IV.1-I.C '. IV.1656), where for the compounds R1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compound I.C'. V, whichWherein Q is Q3，R4Is hydrogen, R5Is hydrogen, R6cIs methyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs ethyl:
TABLE 29 Compounds of the formula I.C '. V (I.C '. V.1-I.C '. V.1656), where for the compounds R1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compounds I.C'. VI in which Q is Q3，R4Is hydrogen, R5Is hydrogen, R6cIs ethyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs ethyl:
TABLE 30 Compounds of the formula I.C.. VI (I.C.. VI.1-I.C.. VI.1656), where R for the compounds1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compounds I.C'. VII in which Q is Q3，R4Is hydrogen, R5Is fluorine, R6cIs methyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs H:
TABLE 31 Compounds of the formula I.C '. VII (I.C '. VII.1-I.C '. VII.1656), where for the compounds R1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compound I.C'. VIII, wherein Q is Q3，R4Is hydrogen, R5Is fluorine, R6cIs ethyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs H:
TABLE 32 Compounds of the formula I.C '. VIII (I.C '. VIII.1-I.C '. VIII.1656), where for the compounds R1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compounds I.C'. IX, wherein Q is Q3，R4Is hydrogen, R5Is fluorine, R6cIs methyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs a methyl group:
TABLE 33 Compounds of the formula I.C '. IX (I.C '. IX.1-I.C '. IX.1656), where for the compounds R1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compound i.c'. X wherein Q is Q3，R4Is hydrogen, R5Is fluorine, R6cIs ethyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs a methyl group:
TABLE 34 Compounds of the formula I.C '. X (I.C '. X.1-I.C '. X.1656), where for the compounds R1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compounds I.C'. XI where Q is Q3，R4Is hydrogen, R5Is fluorine, R6cIs methyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs ethyl:
TABLE 35 Compounds of the formula I.C.. XI (I.C.. XI.1-I.C.. XI.1656), where for the compounds R is1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compounds I.C'. XII, in which Q is Q3，R4Is hydrogen, R5Is fluorine, R6cIs ethyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs ethyl:
TABLE 36 Compounds of the formula I.C '. XII (I.C '. XII.1-I.C '. XII.1656), where for the compounds R is1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compounds I.D'. I, wherein Q is Q4，R4Is hydrogen, R5Is hydrogen, R6dIs methyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs H:
TABLE 37 Compounds of the formula I.D '. I (I.D '. I.1-I.D '. I.1656), where for the compounds R1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compounds I.D'. II in which Q is Q4，R4Is hydrogen, R5Is hydrogen, R6dIs ethyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs H:
TABLE 38 Compounds of the formula I.D '. II (I.D '. II.1-I.D '. II.1656), where R for the compounds1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compounds I.D'. III, where Q is Q4，R4Is hydrogen, R5Is hydrogen, R6dIs methyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs a methyl group:
TABLE 39 Compounds of the formula I.D '. III (I.D '. III.1-I.D '. III.1656), where for the compounds R1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compounds I.D'. IV, wherein Q is Q4，R4Is hydrogen, R5Is hydrogen, R6dIs ethyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs a methyl group:
TABLE 40 Compounds of the formula I.D '. IV (I.D '. IV.1-I.D '. IV.1656), where R for the compounds1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compounds I.D'. V, wherein Q is Q4，R4Is hydrogen, R5Is hydrogen, R6dIs methyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs ethyl:
TABLE 41 Compounds of the formula I.D '. V (I.D '. V.1-I.D '. V.1656), where for the compounds R1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compounds I.D'. VI in which Q is Q4，R4Is hydrogen, R5Is hydrogen, R6dIs ethyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs ethyl:
TABLE 42 Compounds of the formula I.D '. VI (I.D '. VI.1-I.D '. VI.1656), where for the compounds R1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compounds I.D'. VII in which Q is Q4，R4Is hydrogen, R5Is fluorine, R6dIs methyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs H:
TABLE 43 Compounds of the formula I.D '. VII (I.D '. VII.1-I.D '. VII.1656), where R for the compounds1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compounds I.D'. VIII, in which Q is Q4，R4Is hydrogen, R5Is fluorine, R6dIs ethyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs H:
TABLE 44 Compounds of the formula I.D '. VIII (I.D '. VIII.1-I.D '. VIII.1656), where for the compounds R is1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compounds I.D'. IX, wherein Q is Q4，R4Is hydrogen, R5Is fluorine, R6dIs methyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs a methyl group:
TABLE 45 Compounds of the formula I.D '. IX (I.D '. IX.1-I.D '. IX.1656), where for the compounds R is1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compound i.d'. X wherein Q is Q4，R4Is hydrogen, R5Is fluorine, R6dIs ethyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs a methyl group:
TABLE 46 Compounds of the formula I.D '. X (I.D '. X.1-I.D '. X.1656), where for the compounds R1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compounds I.D'. XI where Q is Q4，R4Is hydrogen, R5Is fluorine, R6dIs methyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs ethyl:
TABLE 47 Compounds of the formula I.D '. XI (I.D '. XI.1-I.D '. XI.1656), where for the compounds R is1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a;
compounds I.D'. XII, in which Q is Q4，R4Is hydrogen, R5Is fluorine, R6dIs ethyl, R7Is hydrogen, Z2Is a covalent bond, and R2cIs ethyl:
TABLE 48 Compounds of the formula I.D '. XII (I.D '. XII.1-I.D '. XII.1656), where for the compounds R is1、R2a、R2bAnd R3The combination of (a) corresponds in each case to one row of table a.
Table a:
in table a, the following abbreviations are used:
c-C3H5a cyclopropyl group;
C6H5phenyl radical
4-Cl-C6H44-chlorophenyl group
4-CH3-C6H44-methylphenyl radical
4-CH3O-C6H44-methoxyphenyl radical
2,6-(CH3)2-C6H32, 6-dimethylphenyl
In a particular embodiment, compound I is selected from the group consisting of the example compounds, N-oxides thereof, and agriculturally acceptable salts thereof.
The compounds of formula I may be prepared by standard methods of organic chemistry, for example by the methods described in the schemes below. If not otherwise stated, the substituents, variables and indices used in the schemes are as defined above for the compounds of formula I.
Wherein R is2cThe compound of formula I that is H can be prepared from the corresponding benzamide of formula II, which comprises reacting the compound of formula II with thiophosgene (III) to obtain the isothiocyanate of formula IV. Subsequent reaction of (IV) with ammonia or an amine of formula V to give a compound of formula (I) wherein R2cFor H, the process is described in scheme 1 below.
Scheme 1:
the reaction of the compound of the formula II with thiophosgene III or a thiophosgene equivalent and a secondary amine of the formula V can be carried out analogously to the preparation of mixed thioureas by reacting two different amines with thiophosgene or a thiophosgene equivalent. Typically, the compound of formula II is first reacted with thiophosgene to give the Isothiocyanate (IV) as an intermediate compound, which is subsequently reacted with a secondary amine of formula IV. The isothiocyanate of formula IV can be isolated from the reaction mixture. For economic reasons, Isothiocyanate (IV) is usually not isolated, but the reaction mixture obtained by reacting compound (II) with thiophosgene or a thiophosgene equivalent is reacted with ammonia or an amine of the formula V.
Further details can be taken from the preparation examples contained herein. In addition to this, the skilled person will easily find suitable reaction conditions for the synthesis described in scheme 1 by routine.
In a similar manner, compounds of formula (II ') can be reacted with isothiocyanate compounds (IV') prepared from primary amines (V), wherein R is2bIs H, R2aInstead of H, to give compounds of the formula I, in which R2bIs H, R2aInstead of H, the reaction is shown in scheme 2:
and (2) a flow scheme:
the compounds of formulae (II) and (II') are known, for example from WO 2017/102275, or can be readily prepared according to standard procedures by methods analogous to those described in WO 2017/102275, or from the corresponding 3-nitrobenzamide compounds or 3-cyanobenzamide compounds by reduction of the 3-nitro or 3-cyano group, respectively.
A compound of formula I, wherein R7In particular H, can also be prepared by the reaction described in scheme 3 below.
And (3) a flow path:
the compound of formula VI may be reacted with a benzoyl compound of formula VII to give a compound of formula I, wherein R is7Is hydrogen. Here, X is a leaving group, such as a halogen, in particular Cl, an anhydride residue or an active ester residue. Especially in the case where X is halogen, the reaction is suitably carried out in the presence of a base. Suitable bases are, for example, carbonates, such as lithium, sodium, potassium or cesium carbonate, amines, such as trimethylamine or triethylamine, and basic N-heterocycles, such as pyridine, 2, 6-lutidine or 2,4, 6-collidine. Suitable solvents are in particular aprotic solvents, for example pentane, hexane, heptane, octane, cyclohexane, dichloromethane, chloroform, 1, 2-dichloroethane, benzene, chlorobenzene, toluene, xylene, dichlorobenzene, trimethylbenzene, pyridine, 2, 6-lutidine, 2,4, 6-collidine, acetonitrile, diethyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, methyl tert-butyl ether, 1, 4-dioxane, N-dioxane, methyl tert-butyl ether, methyl tertMethyl formamide, N-methyl pyrrolidone, or mixtures thereof. The starting materials are generally reacted with one another in equimolar or near equimolar amounts at reaction temperatures generally in the range from-20 ℃ to 100 ℃ and preferably in the range from-5 ℃ to 50 ℃.
Alternatively, the compounds of formula I can also be prepared as shown in scheme 4 below. Reaction of an amino compound of formula VI with a benzoic acid compound of formula VIII in the presence of an activating compound to give a compound of formula I, wherein R7In particular H. The reaction of compound (VI) with compound (VIII) is preferably carried out in the presence of a suitable activator which converts the carboxyl group of compound (VIII) into an activated ester or amide. For this purpose, activators known in the art, such as 1,1', Carbonyldiimidazole (CDI), Dicyclohexylcarbodiimide (DCC), 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide (EDC) or 2,4, 6-tripropyl-1, 3,5,2,4, 6-trioxatriphospha-cyclohexane-2, 4, 6-trioxide (T3P), can be used. In particular, depending on the particular activator used, the activated ester or amide may be formed in situ by contacting the benzoic acid compound of formula VIII with the activator in the presence of the amine compound of formula VI, or in a separate step prior to reaction with the amine compound of formula VIII. In the activation reaction, especially in the case where DCC or EDC is used as the activator, it may be advantageous to include other additives, such as hydroxybenzotriazole (HOBt), nitrophenol, pentafluorophenol, 2,4, 5-trichlorophenol or N-hydroxysuccinimide. It may be further advantageous to prepare the activated ester or amide in the presence of a base such as a tertiary amine. The active ester or amide is reacted in situ or subsequently with an amine of formula III or IV to give an amide of formula I. The reaction is usually carried out in an anhydrous inert solvent, for example a chlorinated hydrocarbon, for example dichloromethane or dichloroethane, an ether, for example tetrahydrofuran or 1, 4-dioxane, or a carboxamide, for example N, N-dimethylformamide, N-dimethylacetamide or N-methylpyrrolidone. The reaction is generally carried out at a temperature of from-20 ℃ to +50 ℃ depending on the reactivity of the compounds (VI) and (VIII), respectively, and the activator used.
And (4) a flow chart:
the compounds of formula VI are commercially available or can be obtained according to standard methods of organic chemistry. For example, where Q is Q1And R is6aCompounds of formula VI which are alkyl or similar groups may be prepared from 5-aminotetrazole according to the method described in Journal of the American chemical society,1954,76, 923-. Or, wherein Q is Q1According to the method described in Journal of the American Chemical Society,1954,76,88-89, from 3- (R)6a) -substituted 1-aminoguanine.
Wherein Q is Q2And R is6bCompounds of formula VI which are alkyl or the like may be prepared from 3-amino-1, 2, 4-triazole by reacting 1- (R) with 1- (R) according to the procedure described in Zeitschrift f ü R Chemie,1990,30,12, 436-one 4376b) -substituted 1-aminoguanine with formic acid.
Wherein Q is Q3The compounds of formula VI are commercially available or can be prepared by standard methods analogous to those known in the literature for the preparation of 4-amino-1, 2, 5-oxadiazole compounds. For example, 3- (R)6c) The-substituted-4-amino-1, 2, 5-oxadiazoles can be prepared from β -keto esters according to the method described in Russian Chemical Bulletin, int. Ed.,54(4),1032-1037(2005) where Q is Q3And wherein R6cCompounds of formula VI which are halogen may be prepared from commercially available 3, 4-diamino-1, 2, 5-oxadiazoles according to the procedures described in the literature, for example by Sandmeyer type reactions as described in Heteroatom Chemistry,15(3),199-207 (2004). According to the method described in Journal of Chemical Research, Synopses (6),190(1985), Izvistya Akademii Nauk SSSR, Seriya Khimichekaya (9),2086-8(1986), Russian Chemical Bulletin (translated from Izvistya AkademiNauk, Seriya Khimichekaya), 53(3),596-3And wherein R6cThe compound of formula VI, which is a halogen, is used as a starting material for introducing further substituents R6c by nucleophilic substitution.
Wherein Q is Q4The compounds of the formula VI are known or can be prepared analogously to the criteria known in the literature for preparing 2-amino-1, 3, 4-oxadiazole compoundsThe preparation method is as follows. For example, 5- (R)6d) Substituted-2-amino-1, 3, 4-oxadiazoles can be prepared from aldehydes and semicarbazides according to the method described in j.org.chem.,2015,80, 1018-1024. 5- (R)6d) Substituted-2-amino-1, 3, 4-oxadiazoles can also be prepared by intramolecular cyclization of semicarbazones by the procedure described in Synlett,2015,26,1201-1206. Preparation of 5- (R)6d) Other methods of-substitution of-2-amino-1, 2, 5-oxadiazoles are described in org.lett.,2014,16, 2342-.
The compounds of formulae VII and VIII can be prepared from the corresponding 3-aminobenzoic acid compounds according to standard methods for preparing thioureas, for example, by methods analogous to those described in schemes 1 and 2.
In addition to this, the compounds of formula VI and benzoic acid precursors of formulae VII and VIII are known or can also be prepared by methods known in the art.
Wherein R is2bOr R2cCompounds of formula I other than hydrogen may be prepared from those in which R is2bOr R2cCompounds of formula I which are hydrogen are prepared by standard procedures analogous to N-substitution of urea and thiourea, respectively. Wherein R is7Compounds of formula I other than hydrogen may be prepared from those in which R is7The compounds of formula I which are hydrogen are prepared by methods analogous to the standard methods for N-substitution of carboxamides.
In general, compounds of formula I, including stereoisomers, salts and tautomers thereof and precursors in methods of synthesis thereof, can be prepared by the methods described above. If individual compounds cannot be prepared by the above-described routes, they can be prepared by derivatization of other compounds I or of the respective precursors or by routine modification of the synthetic routes. For example, in individual cases, certain compounds of formula I may be advantageously prepared from other compounds of formula I by derivatization, e.g., by ester hydrolysis, amidation, esterification, ether cleavage, olefination, reduction, oxidation, and the like, or by conventional modification of the synthetic routes described.
The reaction mixture is worked up in a conventional manner, for example by mixing with water, separating the phases and, if appropriate, chromatographically purifying the crude product, for example by chromatography on alumina or silica gel. Certain intermediates and end products can be obtained as colorless or pale brown viscous oils, which are isolated or purified from volatile components under reduced pressure and at mildly elevated temperatures. If the intermediates and final products are obtained as solids, purification can be carried out by recrystallization or trituration.
The compounds of the formula I and their agriculturally suitable salts can be used as herbicides. They may be used as such or may be used as suitably formulated compositions. Herbicidal compositions comprising compound I, its N-oxide or salt (especially preferred aspects thereof) are very effective against non-crop area plants, especially at high application rates. They act on broadleaf weeds and grassy weeds in crops such as wheat, rice, corn, soybeans and cotton without causing any significant damage to the crop. This effect is mainly observed at low application rates.
Depending on the application method, the compounds of the formula I, in particular their preferred aspects, or the compositions comprising them, can additionally be used in many other crops to eliminate undesirable vegetation. Examples of suitable crops are as follows:
onion (Allium cepa), pineapple (Ananas comosus), groundnut (Arachis hypogaea), Asparagus (Asparagus officinalis), oat (Avena sativa), beet (Beta vulgaris, Asparagus), rape (Brassica napus), kale (Brassica napus), Asparagus (napobrassica), turnip (Brassica napus), safflower (Carthamus), hickory (carolina), kale (Brassica oleracea), black mustard (Brassica nigra), Camellia sinensis (camllia), safflower (Carthamus), hickory (carolina), lemon (Citrus limonum), sweet potato (Citrus sinensis), coffee (carob), carrot (carob), olive), strawberry (carob), coffee (carob), carrot (carob), strawberry (carob), carrot (carob), olive), carrot (carob), olive (carob), olive), green (carob), green fruit (green fruit), green fruit (green fruit), green fruit (green fruit), green fruit (green fruit) and green fruit (green, Hevea brasiliensis, barley (Hordeum vulgare), hop (Humulus lupulus), sweet potato (Ipomoea batatas), walnut (Juglans regia), lentil (Lens cularis), flax (Linum usitatissimum), tomato (Lycopersicon lycopersicum), apple (Malus spec), cassava (Manihot esculenta), alfalfa (Medicasactiva), banana (Musa spec), tobacco (Nicorandia microbacterium) (yellow. tobacco (N.rutilus)), olive (Oleaeuropeia), rice (Oryza sativa), golden white fungus (Phaseolus), bean (Seolus vulgaris), European almond (Pisceia), pine (Picea), apricot (Prunus vulgaris), Prunus vulgaris (Prunus humilis), Prunus cerasus (Prunus humilis), Prunus ceratus (Prunus ceratus), Prunus ceratus) and Prunus ceratus (cornus Prunus), Prunus humilis), Prunus ceratus (cornus ceratus) seed (Prunus humilis), Prunus Prunus) A. Prunus, Prunus humilis, Prunus ceratus (cornus Prunus) and Prunus Prunus) are, Prunus humilis, Prunus Prunus, Prunus humilis, Prunus Prunus, Prunus ceratus (cornus Prunus, Prunus, White mustard (Sinapis alba), potato (solanum tuberosum), Sorghum bicolor (Sorghum (s. vulgare)), cacao (theobroma cacao), red clover (Trifolium pratense), Triticum aestivum (Triticum aestivum), Triticale (Triticale), durum wheat (Triticum durum), broad bean (Vicia faba), grape (Vitis vinifera), maize (Zea mays).
The compounds of the invention are particularly suitable for gramineous crops, in particular Tribum triticae crops, such as barley (sorghum), sorghum (sorghum), wheat (triticum) and rye (secale) crops, and maize (zea) crops, such as maize, and rice (oryza), such as rice.
The term "crop" also includes plants that have been modified by breeding, mutagenesis, or genetic engineering. Genetically modified plants are plants whose genetic material has been modified by crossing, mutation or natural recombination (i.e.recombination of genetic information) in a manner which does not occur under natural conditions. Here, one or more genes are often integrated into the genetic material of the plant to improve plant performance.
Thus, the term "crop plants" also includes plants which have been rendered tolerant to certain classes of herbicides, such as inhibitors of hydroxyphenylpyruvate dioxygenase (HPPD), inhibitors of acetolactate synthase (ALS) such as sulfonylureas (EP-A-0257993, U.S. Pat. No. 5,013,659) or imidazolinones (see, for example, U.S. Pat. No. 6,222,100, WO01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073), inhibitors of enolpyruvylshikimate 3-phosphate synthase (EPSPS) such as glyphosate (glyphosate) (see, for example, WO 92/00377), inhibitors of Glutamine Synthetase (GS) such as glufosinate (glufosinate) (see, for example, EP-A-0242236, glufosinate), EP-A-242246) or oxonil herbicides (see, for example, US 5,559,024).
In a preferred embodiment, the term "crop plant" refers to a plant comprising in its genome a gene encoding an herbicide tolerant wild-type or mutant HPPD protein. Such a gene may be an endogenous gene or a transgene, as described below.
"herbicide tolerant" or "herbicide resistant" plants refer to plants that are tolerant or resistant to at least one herbicide at levels that would normally kill or inhibit the growth of normal or wild-type plants. By "herbicide-tolerant wild-type or mutant HPPD protein" or "herbicide-resistant wild-type or mutant HPPD protein" is meant that a reference wild-type HPPD protein exhibits a higher HPPD activity relative to the HPPD activity of the wild-type or reference HPPD protein when at least one herbicide known to interfere with HPPD activity is present and the concentration or level of the herbicide is known to inhibit HPPD activity of the reference HPPD protein. Furthermore, the HPPD activity of such herbicide tolerant or herbicide resistant HPPD proteins may be referred to herein as "herbicide tolerant" or "herbicide resistant" HPPD activity.
The term "mutated HPPD nucleic acid" refers to a HPPD nucleic acid having a sequence that is mutated from a wild-type HPPD nucleic acid and which confers enhanced tolerance to a "HPPD-inhibiting herbicide" to plants expressing it. Furthermore, the term "mutated hydroxyphenylpyruvate dioxygenase (mutated HPPD)" refers to the replacement of an amino acid of the wild-type primary sequence SEQ ID NO:2, 5,8, 11, 14, 17, 20, 22, 24, 26, 28, 30, 32, 34, 36, 38, 40, 42, 44, 46, 48, 50, 53, 55, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, a variant, derivative, homologue, ortholog or paralog thereof with another amino acid. The expression "mutated amino acid" will be used hereinafter to denote an amino acid that is replaced by another amino acid, thus indicating a site of mutation in the primary sequence of the protein.
Examples
The preparation of the compounds of formula I is illustrated by the examples; however, the subject matter of the present invention is not limited to the given examples. Other compounds I were obtained using the procedures given in the examples below, with appropriate modifications of the starting materials. The compounds obtained in this way are listed in table C together with the physical data. The products shown below were characterized by determination of the melting point, NMR spectrum or mass ([ m/z ]) determined by HPLC-MS spectrum.
HPLC-MS, high performance liquid chromatography and mass spectrum are combined;
MeOD-tetradeuterated methanol
MS mass spectrum
THF tetrahydrofuran
TFA trifluoroacetic acid
single peak of s
d double peak
t is triplet
m is multiplet
HPLC column RP-18 column (Chromolith Speed ROD from Merck KgaA, Germany),50 × 4.6 mm; mobile phase acetonitrile + 0.1% TFA/water + 0.1% TFA, gradient from 5:95 to 100:0 over 5 min, flow rate 1.8mL/min at 40 ℃.
MS quadrupole electrospray ionization, 80V (positive mode).
HPLC column, Luna-C18(2)5 μm column (Phenomenex),2.0 x 50 mm; mobile phase acetonitrile + 0.0625% TFA/water + 0.0675% TFA, using a gradient from 10:90 to 80:20 over 4.0 min at 40 ℃ and a flow rate of 0.8mL/min.
MS quadrupole electrospray ionization, 70V (positive mode).