阅读说明：本技术 杀有害生物活性的介离子杂环化合物 (Pesticidally active mesoionic heterocyclic compounds ) 是由 P·J·M·容 R·杜梅尼尔 J·D·H·加格尼佩恩 A·斯托勒 S·伦迪妮 于 2018-12-07 设计创作，主要内容包括：具有式I,(I)的化合物,其中取代基是如权利要求(1)中所定义的,以及那些化合物的农用化学上可接受的盐、立体异构体、对映异构体、互变异构体和N-氧化物可以用作杀昆虫剂。<Image he="539" wi="700" file="DDA0002536697720000011.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>(Compounds of formula I, (I) wherein the substituents are as defined in claim (1), and the agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds can be used as insecticides.)

1. a compound having the formula I,

wherein

W is S or O;

v is S or O;

R_1aand R_1bIndependently hydrogen, halogen, amino, hydroxy, C₁-C₆Alkyl radical, C₁-C₆Haloalkyl, C₁-C₆Haloalkoxy, C₁-C₆Alkoxy, or cyano;

R₂is hydrogen, halogen, hydroxy, amino, cyano, C₁-C₆Alkyl, mono-or polysubstituted C₁-C₆An alkyl group, wherein the substituents are independently selected from the group consisting of: halogen, hydroxy, amino, cyano, nitro, C₁-C₆Haloalkoxy, C₁-C₆Alkoxy, triazoles, pyrazoles, imidazolesAnd tetrazole, wherein the triazole, pyrazole, imidazole, and tetrazole can be mono-or polysubstituted with substituents independently selected from the group consisting of: halogen, C₁-C₄Alkyl radical, C₁-C₄Alkoxy radical, C₁-C₄Haloalkyl and cyano;

R₃is hydrogen or C₁-C₆An alkyl group;

R₄is hydrogen or a 5-or 6-membered heteroaromatic ring Y optionally independently substituted with substituents selected from the group U, wherein Y is a ring selected from Y1 to Y29

n is 0, 1,2 or 3;

z is hydrogen, cyano, nitro, hydroxy, C₁-C₄Alkyl radical, C₁-C₄Haloalkyl, C₁-C₄Alkoxy or C₁-C₄A haloalkoxy group;

u is independently selected from the group consisting of: halogen, cyano, nitro, hydroxy, amino, C₁-C₄Alkyl radical, C₁-C₄Haloalkyl, C₁-C₄Alkoxy radical, C₁-C₄Haloalkoxy, C₁-C₄halogenoalkoxy-C₁-C₄Alkyl radical, C₁-C₄alkoxy-C₁-C₄Alkyl radical, C₁-C₄Alkylsulfanyl group, C₁-C₄Alkylsulfinyl radical, C₁-C₄Alkylsulfonyl radical, C₁-C₄Halogenoalkylsulfanyl group, C₁-C₄Haloalkylsulfinyl radical, C₁-C₄Haloalkylsulfonyl, and cyclopropyl;

R₅is C₁-C₆Alkyl radical, C₃-C₆Cycloalkyl radical, C₁-C₆Haloalkyl, or C₁-C₆An alkoxy group; or

R₅Is phenyl, the ring systems of either being independently selectedMono-or polysubstituted with substituents selected from: halogen, C₁-C₄Alkyl radical, C₁-C₄Haloalkyl, C₁-C₄Alkoxy and C₁-C₄A haloalkoxy group; and is

R₆Is a 5 to 12 membered aromatic ring, which may be monocyclic or polycyclic, said ring system may be independently selected from the group U₂Is mono-or polysubstituted; or

R₆Is a3 to 12 membered heteroaromatic ring or a saturated or partially saturated heterocyclic ring, each of said ring systems may be monocyclic or polycyclic, said ring systems may contain 1 to 4 heteroatoms selected from the group consisting of: nitrogen, oxygen and sulfur, with the proviso that each ring system cannot contain more than 2 oxygen atoms or more than 2 sulfur atoms, wherein the nitrogen heteroatom can be substituted by Z and the 3-to 12-membered ring system can be independently selected from the group U₂Is mono-or polysubstituted; or

R₆Is hydrogen, amino, halogen, cyano, C₁-C₆Haloalkoxy, C₁-C₆Alkoxy radical, C₁-C₄Alkylsulfanyl group, C₁-C₄Alkylsulfinyl radical, C₁-C₄Alkylsulfonyl radical, C₁-C₄Halogenoalkylsulfanyl group, C₁-C₄Haloalkylsulfinyl radical, C₁-C₄Haloalkylsulfonyl group, C₂-C₆Alkenyl radical, C₂-C₆Haloalkenyl, C₂-C₆Alkynyl, C₂-C₆Haloalkynyl, benzyl optionally mono-or polysubstituted by halogen (which may be the same or different in the case of polysubstitution), or-C (O) R₇Or is or

R₆Is C₁-C₆Alkyl, optionally independently selected from the group U₃Is mono-or polysubstituted with a substituent of (a), or

R₆Is C₃-C₆Cycloalkyl optionally mono-or polysubstituted with substituents independently selected from the group U; wherein

U₂Is halogen, nitro, cyano, ammoniaRadical, hydroxy, -SCN, -CO₂H、C₁-C₆Alkyl radical, C₃-C₆Cycloalkyl radical, C₃-C₆Halogenocycloalkyl, C₃-C₆cycloalkyl-C₁-C₄Alkyl radical, C₃-C₆halogenocycloalkyl-C₁-C₄Alkyl radical, C₁-C₆Haloalkyl, C₁-C₆Alkoxy radical, C₁-C₄alkoxy-C₁-C₄Alkyl radical, C₁-C₄alkoxy-C₁-C₄Alkoxy, cyano-C₁-C₄Alkyl, cyano-C₁-C₄Haloalkyl, C₂-C₆Alkenyl radical, C₂-C₆Haloalkenyl, C₂-C₆Alkynyl, C₂-C₆Halogenated alkynyl, C₁-C₆Haloalkoxy, C₁-C₄halogenoalkoxy-C₁-C₄Alkyl radical, C₁-C₆Alkylsulfanyl group, C₁-C₆Alkylsulfinyl radical, C₁-C₆Alkylsulfonyl radical, C₁-C₆Halogenoalkylsulfanyl group, C₁-C₆Haloalkylsulfinyl radical, C₁-C₆Haloalkylsulfonyl group, C₁-C₆Alkylcarbonyl group, C₁-C₆Alkoxycarbonyl group, C₁-C₆Halogenoalkylcarbonyl group, C₁-C₆Haloalkoxycarbonyl, (C)₁-C₆Alkyl) NH, (C)₁-C₆Alkyl radical)₂N、(C₃-C₆Cycloalkyl) NH, (C)₃-C₆Cycloalkyl radicals₂N、C₁-C₆Alkylcarbonylamino, C₃-C₆Cycloalkyl carbonylamino group, C₁-C₆Haloalkylcarbonylamino, C₃-C₆Halocycloalkylcarbonylamino radical, C₁-C₆Alkylaminocarbonyl radical, C₃-C₆Cycloalkylaminocarbonyl group, C₁-C₆Haloalkylaminocarbonyl group, C₃-C₆Halocycloalkylaminocarbonyl group, C₃-C₆A cycloalkyl carbonyl group,C₃-C₆Halocycloalkylcarbonyl, -SF₅or-C (O) NH₂；

U₃Is halogen, nitro, cyano, amino, hydroxy, C₁-C₆Alkyl radical, C₃-C₆Cycloalkyl radical, C₃-C₆Halogenocycloalkyl, C₃-C₆cycloalkyl-C₁-C₄Alkyl radical, C₃-C₆halogenocycloalkyl-C₁-C₄Alkyl radical, C₁-C₆Haloalkyl, C₁-C₆Alkoxy radical, C₁-C₄alkoxy-C₁-C₄Alkyl radical, C₁-C₄alkoxy-C₁-C₄Alkoxy, cyano-C₁-C₄Alkyl, cyano-C₁-C₄Haloalkyl, C₂-C₆Alkenyl radical, C₂-C₆Haloalkenyl, C₂-C₆Alkynyl, C₂-C₆Halogenated alkynyl, C₁-C₆Haloalkoxy, C₁-C₄halogenoalkoxy-C₁-C₄Alkyl radical, C₁-C₆Alkylsulfanyl group, C₁-C₆Alkylsulfinyl radical, C₁-C₆Alkylsulfonyl radical, C₁-C₆Halogenoalkylsulfanyl group, C₁-C₆Haloalkylsulfinyl radical, C₁-C₆Haloalkylsulfonyl group, C₁-C₆Alkylcarbonyl group, C₁-C₆Alkoxycarbonyl group, C₁-C₆Halogenoalkylcarbonyl or C₁-C₆A haloalkoxycarbonyl group; or

U₃Is a 5 to 6 membered aromatic ring, heteroaromatic ring, or a saturated or partially saturated carbocyclic or heterocyclic ring (wherein the heteroaromatic ring and heterocyclic ring may contain 1 to 4 heteroatoms selected from the group consisting of substituted or unsubstituted nitrogen, oxygen and sulfur, with the proviso that each ring system cannot contain more than 2 oxygen atoms or more than 2 sulfur atoms), wherein the 5 to 6 membered ring system may be mono-or polysubstituted with substituents independently selected from the group U; and is

R₇Is hydrogen,Amino, halogen, cyano, C₁-C₆Alkyl radical, C₁-C₆Haloalkyl, C₁-C₆Alkoxy radical, C₁-C₆Haloalkoxy, C₁-C₄Halogenoalkoxy radical C₁-C₄Alkyl radical, C₁-C₆alkoxy-C₁-C₆Alkyl radical, C₂-C₆Alkenyl radical, C₂-C₆Haloalkenyl, C₂-C₆Alkynyl or C₂-C₆A haloalkynyl group; or

R₇Is a 5 to 6 membered aromatic ring, heteroaromatic ring, or a saturated or partially saturated carbocyclic or heterocyclic ring (wherein the heteroaromatic ring and heterocyclic ring may contain 1 to 4 heteroatoms selected from the group consisting of substituted or unsubstituted nitrogen, oxygen and sulfur, with the proviso that each ring system cannot contain more than 2 oxygen atoms and more than 2 sulfur atoms), wherein the 5 to 6 membered ring system may be mono-or polysubstituted with substituents independently selected from the group U; or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof.

2. The compound of claim 1, wherein R₄Is hydrogen or a 5 or 6 membered heteroaromatic ring selected from Y4, Y9, and Y12, U is selected from the group consisting of: halogen and trifluoromethyl, and n is 0, 1.

3. A compound according to claim 1 or claim 2, wherein R₆Is hydrogen, iodine, -C (O) R₇(wherein R is₇Is trifluoromethyl or phenyl), phenyl optionally mono-or polysubstituted by the group consisting of halogen and trifluoromethyl, naphthyl optionally substituted by halogen (in the case of polysubstitution, may be the same or different), pyridylphenyl optionally mono-or polysubstituted by substituents independently selected from halogen and trifluoromethyl, or C optionally mono-or polysubstituted by substituents independently selected from chlorine and fluorine₁-C₄An alkyl group.

4. According to claim1 wherein W and V are each O, R_1aAnd R_1bEach is hydrogen; r₂Selected from the group consisting of hydrogen, trifluoromethyl, trifluoroethyl, and cyanomethyl; r₃Is hydrogen; r₄Is hydrogen or a 5-or 6-membered heteroaromatic ring selected from Y1, Y3, Y4, Y5, Y7, Y9, Y12, Y18, Y21 and Y23, wherein Z is C₁-C₄Alkyl, U is selected from the group consisting of: halogen, C₁-C₄Haloalkyl, C₁-C₄Alkoxy, cyano, C₁-C₄Alkylsulfanyl and C₁-C₄Alkylsulfonyl, and n is 0, 1; preferably wherein Z is methyl and U is selected from the group consisting of: halogen, trifluoromethyl, methoxy, cyano, methylsulfanyl and methylsulfonyl, and n is 0, 1; r₅Is methyl, ethyl, trifluoroethyl or cyclopropyl; and R is₆Is hydrogen, halogen, -C (O) R₇(wherein R is₇Is C₁-C₆Haloalkyl, phenyl or halophenyl), optionally substituted by halogen, C₁-C₆Haloalkyl, C₁-C₆Haloalkoxy and C₁-C₄A phenyl group which is mono-or polysubstituted with a halogenoalkylsulfanyl group, a benzyl group which is optionally mono-or polysubstituted with a halogen (which may be the same or different in the case of polysubstitution), a naphthyl group which is optionally substituted with a halogen independently selected from halogen and C₁-C₄A pyridylphenyl group which is mono-or polysubstituted with a substituent of a haloalkyl group, a C group which is optionally mono-or polysubstituted with a substituent independently selected from the group consisting of halogen (in the case of polysubstitution, they may be the same or different)₁-C₄Alkyl, or C₃-C₆A cycloalkyl group.

5. The compound of claim 1, wherein W and V are each O, R_1aAnd R_1bEach is hydrogen; r₂Selected from trifluoromethyl, trifluoroethyl and cyanomethyl; r₃Is hydrogen; r₄Is hydrogen; r₅Is methyl, ethyl, trifluoroethyl, or cyclopropyl; and R is₆Is hydrogen, halogen, -C(O)R₇(wherein R is₇Is C₁-C₆Haloalkyl, phenyl or halophenyl), optionally substituted by halogen, C₁-C₆Haloalkyl, C₁-C₆Haloalkoxy and C₁-C₄A phenyl group which is mono-or polysubstituted with a halogenoalkylsulfanyl group, a benzyl group which is optionally mono-or polysubstituted with a halogen (which may be the same or different in the case of polysubstitution), a naphthyl group which is optionally substituted with a halogen independently selected from halogen and C₁-C₄A pyridylphenyl group which is mono-or polysubstituted with a substituent of a haloalkyl group, a C group which is optionally mono-or polysubstituted with a substituent independently selected from the group consisting of halogen (in the case of polysubstitution, they may be the same or different)₁-C₄Alkyl, or C₃-C₆A cycloalkyl group.

6. A compound having the formula IXa, IXb and IXc

Wherein R in each of IXa, IXb and IXc₆Is 3, 5-dichlorophenyl or 3-trifluoromethylphenyl; x in each of IXa, IXb, and IXc is a halogen atom (preferably chlorine); r in formula IXc is methyl or ethyl, and X₀₀Is a halogen atom, or an isourea-containing compound, such as1, 3-dicyclohexyl-isourea-2-yl; and acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides.

7. A compound having the formula X

Wherein R is_1a、R_1b、R₂、R₃、R₄、R₅And R₆Is as defined in any one of claims 1 to 5 and X is halogen (preferably Cl); and canAcceptable salts, stereoisomers, enantiomers, tautomers and N-oxides.

8. A compound having the formula XXI

R₂、R₃、R₄And R₆Is as defined in any one of claims 1 to 5, Ra is hydrogen or methyl, and X is halogen (preferably Cl); and acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides.

9. A compound having the formula XI

Wherein R is_1a、R_1b、R₂、R₃、R₄、R₅And R₆Is as defined in any one of claims 1 to 5, X is halogen (preferably Cl), and A is^-Is an anion, preferably selected from AlCl₄ ^-And Cl^-(ii) a And acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides.

10. A compound having the formula XXII and XXIV

Wherein R is₂、R₃、R₄And R₆Independently of the formulae XXII and XXIV, as defined in any of claims 1 to 5, Ra is hydrogen or methyl, X is halogen (preferably Cl), and A^-Is an anion, preferably selected from AlCl₄ ^-And Cl^-(ii) a And acceptable salts, stereoisomers, enantiomersIsomers, tautomers, and N-oxides.

11. A process for preparing a compound having the formula Ib wherein R is_1a、R_1b、R₂、R₃、R₄、R₅And R₆Is as defined in any one of claims 1 to 5:

(i) the reaction of: compound VI (wherein R_1a、R_1b、R₂、R₃、R₄And R₅Is as defined in any one of claims 1 to 5) with a compound having the formula VIIIa wherein R is aryl or alkyl;

or

(ii) Reaction of a compound having the formula XI, wherein R_1a、R_1b、R₂、R₃、R₄、R₅And R₆Is as defined in any one of claims 1 to 5 and X is halogen such as chlorine, and A^-Is an anion, e.g. AlCl₄ ^-Or Cl^-；

Or

(iii) Reacting: a compound having the formula Id (wherein R_1a、R_1b、R₂、R₃、R₄、R₅And R₆Is as defined in any one of claims 1 to 5), wherein X is a leaving group, with a compound having the formula XIIa, wherein Y is_b1May be a boron-derived functional group; or reacting: a compound having the formula Id, wherein X is a leaving group, and a compound having the formula XIIb, wherein Yb2 is a trialkyltin derivative

12. A pesticidal composition comprising a compound of formula I as defined in any one of claims 1 to 5, one or more formulation additives and a carrier.

13. A combination of active ingredients comprising a compound of formula I as defined in any one of claims 1 to 5, and one or more further active ingredients.

14. A method for controlling insects, acarines, nematodes or molluscs which comprises applying to a pest, to a locus of a pest-preferably a plant, to a plant susceptible to attack by a pest or to a plant propagation material thereof, such as a seed, an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula I as defined in any one of claims 1 to 5 or a composition comprising a compound of formula I as defined in any one of claims 1 to 5, which control is non-therapeutic if on the human or animal body.

15. A plant propagation material comprising one or more compounds of formula I as defined in any one of claims 1 to 5, optionally further comprising a colour pigment, by treatment or coating.