Kill the oxadiazole derivatives of microorganism
阅读说明：本技术 杀微生物的噁二唑衍生物 (Kill the oxadiazole derivatives of microorganism ) 是由 T·J·霍夫曼 D·斯狄尔利 R·比奥德格尼斯 T·皮特纳 R·拉詹 于 2018-03-29 设计创作，主要内容包括：具有式(I)的化合物,其中所述取代基是如在权利要求1中所定义的,所述化合物作为杀有害生物剂、尤其作为杀真菌剂是有用的。<Image he="342" wi="700" file="DDA0002220890430000011.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>(Compound with formula (I), wherein the substituent group is as claimed in claim 1, the compound is useful as pesticides, especially as fungicide.)
1. the compound that one kind has formula (I):
Wherein
N is 0,1 or 2；
A1Indicate N or CR1, wherein R1Indicate hydrogen, halogen or methyl；
A2Indicate N or CR2, wherein R2Indicate hydrogen, halogen or methyl；
A3Indicate N or CR3, wherein R3Indicate hydrogen or fluorine；
A4Indicate N or CR4, wherein R4Indicate hydrogen or fluorine；And
Wherein A1、A2、A3And A4In at least two be C-H；
R5And R6Independently indicate hydrogen, methyl, cyano, difluoromethyl or trifluoromethyl；
R7Indicate hydrogen, hydroxyl, C1-4Alkyl, C1-4Halogenated alkyl, C1-4Alkoxy, hydroxyl C2-4Alkyl, C1-2Alkoxy C2-4Alkyl, C1-2Halogenated alkoxy, C1-2Halogenated alkoxy C2-4Alkyl, C3-4Alkenyl, C3-4Alkynyl, C3-4Alkenyl oxygroup, C3-4Alkynyl oxygroup, C1-4Alkyl carbonyl epoxide, C3-6Naphthenic base or C3-6Naphthenic base C1-2Alkyl；
Z indicates R8, wherein
R8It is C1-6Alkyl, C2-6Alkenyl, C2-6Alkynyl, cyano C1-4Alkyl, C1-4Halogenated alkyl, C1-4Alkoxy C2-4Alkyl, C1-2Halogen For alkoxy C2-4Alkyl, C1-4Alkyl-carbonyl C1-4Alkyl, C1-4Alkoxy carbonyl C1-4Alkyl, C1-4Alkyl carbonyl epoxide C2-4Alkane Base, N-C1-4Alkyl amino-carbonyl C1-4Alkyl, N, bis- C of N-1-4Alkyl amino-carbonyl C1-4Alkyl, N-C1-4Alkyl amino C2-5Alkane Base, N, bis- C of N-1-4Alkyl amino C2-5Alkyl, C1-3Alkyl-carbonyl-amino C2-5Alkyl or C1-4Alkoxycarbonyl amino C2-5Alkane Base；Or
R8It is C3-6Naphthenic base；C3-6Naphthenic base C1-2Alkyl；Phenyl；Phenyl C1-2Alkyl；Heteroaryl or heteroaryl C1-2Alkyl, wherein The heteroaryl moieties are the heteroatomic 5- or 6-membered monocyclic aromatic rings that N, O and S are individually selected from comprising 1,2,3 or 4； Heterocycle；Or heterocycle C1-2Alkyl, wherein the heterocyclyl moieties are the hetero atoms for being individually selected from N, O and S comprising 1 or 2 4 yuan to 6 yuan non-aromatic rings；
Wherein work as R8It is C3-6Naphthenic base, C3-6Naphthenic base C1-2Alkyl, phenyl, phenyl C1-2Alkyl, heteroaryl, heteroaryl C1-2Alkane Base, heterocycle or heterocycle C1-2When alkyl, the C3-6Naphthenic base, phenyl, heteroaryl or heterocycle motif optionally by 1 or 2 substituent groups replace, and the substituent group can be identical or different, are selected from R9；
R9Indicate cyano, fluorine, chlorine, bromine, methyl, difluoromethyl, trifluoromethyl, methoxyl group, ethyoxyl or difluoro-methoxy；And Wherein work as R8It is substituted C3-6When naphthenic base or heterocycle, these rings can contain carbonyl (C=O) or sulfonyl (S (O)2) Group；Or
Z expression-N (R10)R11, wherein
R10Indicate hydrogen, C1-6Alkyl, C1-6Halogenated alkyl, cyano C1-4Alkyl, hydroxyl C2-4Alkyl, C1-2Alkoxy C2-4Alkyl, C1-2 Halogenated alkoxy C1-4Alkyl, C3-6Alkenyl, C3-6Alkynyl, amino C2-4Alkyl, N-C1-4Alkyl amino C2-4Alkyl, N, bis- C of N-1-4 Alkyl amino C2-4Alkyl, formoxyl, C1-4Alkyl-carbonyl, C1-4Alkyl-carbonyl C1-4Alkyl, C1-4Alkoxy carbonyl C1-4Alkyl, C1-4Alkyl carbonyl epoxide C1-4Alkyl, N-C1-4Alkyl amino-carbonyl C1-4Alkyl, N, bis- C of N-1-4Alkyl amino-carbonyl C1-4Alkyl, C1-4Alkoxycarbonyl amino C2-4Alkyl, C1-4Alkyl-carbonyl-amino C2-4Alkyl or C1-4Haloalkylcarbonylamino C2-4Alkyl； Or
R10It is C3-6Naphthenic base；C3-6Naphthenic base C1-2Alkyl；Phenyl；Phenyl C1-2Alkyl；Heteroaryl or heteroaryl C1-2Alkyl, Described in heteroaryl moieties be the heteroatomic 5- or 6-membered monocyclic aromatic for being individually selected from N, O and S comprising 1,2,3 or 4 Ring；Heterocycle；Or heterocycle C1-2Alkyl, wherein the heterocyclyl moieties are to be individually selected from the miscellaneous of N, O and S comprising 1 or 2 4 yuan of atom are to 6 yuan of non-aromatic rings；
Wherein work as R10It is C3-6Naphthenic base, C3-6Naphthenic base C1-2Alkyl, phenyl C1-2Alkyl, phenyl, heteroaryl, heteroaryl C1-2Alkane Base, heterocycle or heterocycle C1-2When alkyl, the C3-6Naphthenic base, phenyl, heteroaryl or heterocycle motif optionally by 1 or 2 substituent groups replace, the substituent group can it is identical or or it is different, be selected from R12；
R12Indicate cyano, fluorine, chlorine, bromine, methyl, difluoromethyl, trifluoromethyl, methoxyl group, ethyoxyl or difluoro-methoxy；And And wherein work as R10It is substituted C3-6When naphthenic base or heterocycle, these rings can contain carbonyl (C=O) or sulfonyl (S (O)2) group；
R11Indicate hydrogen, hydroxyl, C1-4Alkyl, C1-2Halogenated alkyl, C3-4Alkenyl, C3-4Alkynyl, C3-4Naphthenic base, C3-4Naphthenic base C1-2 Alkyl, C1-4Alkoxy, C3-4Alkenyl oxygroup or C3-4Alkynyl oxygroup；Or
Its salt or N- oxide.
2. compound according to claim 1, wherein A1And A2Each independently represent N, C-H or C-F, and A3And A4Respectively From independently indicating C-H or C-F, wherein A1、A2、A3And A4In at least two be C-H.
3. according to claim 1 or compound as claimed in claim 2, wherein R7Be hydrogen, methyl, ethyl, n-propyl, isopropyl, Methoxyl group, cyclopropyl or Cvclopropvlmethvl.
4. compound according to any one of claim 1 to 3, wherein R5And R6Independently indicate hydrogen or methyl.
5. compound according to any one of claim 1 to 4, wherein Z indicates R8, wherein R8It is C1-6Alkyl, C2-6Alkene Base, C2-6Alkynyl, cyano C1-4Alkyl, C1-4Halogenated alkyl, C1-4Alkoxy C2-4Alkyl, C1-2Halogenated alkoxy C2-4Alkyl, C1-4 Alkyl-carbonyl C1-4Alkyl, C1-4Alkoxy carbonyl C1-4Alkyl or C1-4Alkyl carbonyl epoxide C2-4Alkyl；Or
R8It is C3-6Naphthenic base；C3-6Naphthenic base C1-2Alkyl；Phenyl；Phenyl C1-2Alkyl；Heteroaryl or heteroaryl C1-2Alkyl, wherein The heteroaryl moieties are the heteroatomic 5- or 6-membered monocyclic aromatic rings that N, O and S are individually selected from comprising 1,2 or 3；It is miscellaneous Ring group；Or heterocycle C1-2Alkyl, wherein the heterocyclyl moieties are to be individually selected from the heteroatomic of N, O and S comprising 1 or 2 4 yuan to 6 yuan non-aromatic rings；
Wherein work as R8It is C3-6Naphthenic base, C3-6Naphthenic base C1-2Alkyl, phenyl, phenyl C1-2Alkyl, heteroaryl, heteroaryl C1-2Alkane Base, heterocycle or heterocycle C1-2When alkyl, the C3-6Naphthenic base, phenyl, heteroaryl or heterocycle motif optionally by 1 or 2 substituent groups replace, and the substituent group can be identical or different, are selected from R9；
R9Indicate cyano, fluorine, chlorine, bromine, methyl, difluoromethyl, trifluoromethyl, methoxyl group, ethyoxyl or difluoro-methoxy；And Wherein work as R8It is substituted C3-6When naphthenic base or heterocycle, these rings can contain carbonyl (C=O) or sulfonyl (S (O)2) Group.
6. compound according to any one of claim 1 to 5, wherein Z indicates R8, wherein R8It is C1-4Alkyl, C2-4Alkene Base, C2-4Alkynyl, cyano C1-2Alkyl, C1-3Halogenated alkyl, C1-4Alkoxy C2-4Alkyl, C1-2Halogenated alkoxy C2-4Alkyl, C1-3 Alkyl-carbonyl C1-3Alkyl, C1-3Alkoxy carbonyl C1-3Alkyl or C1-3Alkyl carbonyl epoxide C2-4Alkyl；Or
R8It is C3-5Naphthenic base；C3-5Naphthenic base C1-2Alkyl；Phenyl；Phenyl C1-2Alkyl；Heteroaryl or heteroaryl C1-2Alkyl, wherein The heteroaryl moieties are the heteroatomic 5- or 6-membered monocyclic aromatic rings that N, O and S are individually selected from comprising 1,2 or 3；It is miscellaneous Ring group；Or heterocycle C1-2Alkyl, wherein the heterocyclyl moieties are to be individually selected from the heteroatomic of N, O and S comprising 1 or 2 4 yuan to 6 yuan non-aromatic rings；
Wherein work as R8It is C3-5Naphthenic base, C3-5Naphthenic base C1-2Alkyl, phenyl, phenyl C1-2Alkyl, heteroaryl, heteroaryl C1-2Alkane Base, heterocycle or heterocycle C1-2When alkyl, the C3-5Naphthenic base, phenyl, heteroaryl or heterocycle motif optionally by 1 or 2 substituent groups replace, and the substituent group can be identical or different, are selected from R9；
R9Indicate cyano, fluorine, chlorine, bromine, methyl, difluoromethyl, trifluoromethyl or methoxyl group；And wherein work as R8It is substituted C3-5When naphthenic base or heterocycle, these rings can contain carbonyl (C=O) group.
7. compound according to any one of claim 1 to 6, wherein Z indicates R8, wherein R8It is C1-4Alkyl, C3-4Alkene Base, C1-3Halogenated alkyl, C1-2Alkoxy C2-3Alkyl or C1-2Alkoxy carbonyl C1-2Alkyl；Or
R8It is C3-5Naphthenic base；(C3-5Naphthenic base) methyl；Phenyl；Benzyl；Heteroaryl；(heteroaryl) methyl, wherein the heteroaryl Part is the heteroatomic 5 membered monocyclic ring aromatic ring that N, O and S are individually selected from comprising 1 or 2；Heterocycle or (heterocycle) first Base, wherein the heterocyclyl moieties are the heteroatomic 5- or 6-membered non-aromatic rings for being individually selected from N and O comprising 1 or 2；
Wherein work as R8It is C3-5Naphthenic base, (C3-5Naphthenic base) methyl, phenyl, benzyl, heteroaryl, (heteroaryl) methyl, heterocycle, Or when (heterocycle) methyl, the C3-5Naphthenic base, phenyl, heteroaryl or heterocycle motif are optionally taken by 1 or 2 substituent group Generation, the substituent group can be identical or different, are selected from R9；
R9Indicate cyano, fluorine, chlorine, bromine, methyl or methoxy.
8. compound according to any one of claim 1 to 7, wherein Z indicates R8, wherein R8It is methyl, ethyl, positive third Base, isopropyl, normal-butyl, tert-butyl, allyl, propyl- 1- alkenyl, isopropenyl, 1,1- difluoromethyl, 1,1,1- fluoroform Base, 2,2- bis-fluoro ethyls, 2,2,2- trifluoroethyl, 3,3,3- trifluoro propyl, methoxy, methoxy ethyl, methoxyl group carbonyl Ylmethyl, dion e, ethoxy carbonyl methyl, ethoxycarbonylethyl group, cyclopropyl, cyclobutyl, cyclopenta, cyclopropyl Ylmethyl, cyclobutylmethyl, cyclopentyl-methyl, 2,2- difluorocyclopropyl methyl, 2,2- dichloro Cvclopropvlmethvl, phenyl, benzyl, The chloro- 2- fluorophenyl of 2- fluorophenyl, 2,4 difluorobenzene base, 2,4 dichloro benzene base, 4-, the fluoro- 2- chlorphenyl of 4-, pyrazole-3-yl, pyrrole Azoles -4- base, 1- methylpyrazole -3- base, 1- methyl-pyrazol-4-yl, thiophene -2- base, thiene-3-yl, 2- methylthiophene -5- base, 2- methylthiophene -4- base, tetrahydrofuran -2- base, tetrahydrofuran -3- base, tetrahydrofuran -2- ylmethyl, tetrahydrofuran -3- Ji Jia Base, morpholinyl, pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-3-yl, piperidin-1-yl, piperidin-2-yl, piperidines -3- base, Or piperidin-4-yl.
9. compound according to any one of claim 1 to 4, wherein Z expression-N (R10)R11, wherein R10Expression hydrogen, C1-6Alkyl, C1-6Halogenated alkyl, cyano C1-4Alkyl, hydroxyl C2-4Alkyl, C1-2Alkoxy C2-4Alkyl, C1-2Halogenated alkoxy C1-4 Alkyl, C3-6Alkenyl, C3-6Alkynyl, formoxyl, C1-4Alkyl-carbonyl, C1-4Alkyl-carbonyl C1-4Alkyl, C1-4Alkoxy carbonyl C1-4Alkane Base or C1-4Alkyl carbonyl epoxide C1-4Alkyl；Or
R10It is C3-6Naphthenic base, C3-6Naphthenic base C1-2Alkyl, phenyl or phenyl C1-2Alkyl；
Wherein work as R10It is C3-6Naphthenic base, C3-6Naphthenic base C1-2Alkyl, phenyl or phenyl C1-2When alkyl, the C3-6Naphthenic base or Phenyl motif is optionally replaced by 1 or 2 substituent group, the substituent group can it is identical or or it is different, be selected from R12；
R12Indicate cyano, fluorine, chlorine, bromine, methyl, difluoromethyl, trifluoromethyl, methoxyl group, ethyoxyl or difluoro-methoxy；And And wherein work as R10It is substituted C3-6When naphthenic base or heterocycle, these rings can contain carbonyl (C=O) or sulfonyl (S (O)2) group；And
R11Indicate hydrogen, hydroxyl, C1-4Alkyl, C1-2Halogenated alkyl, C3-4Alkenyl, C3-4Alkynyl, C3-4Naphthenic base, C3-4Naphthenic base C1-2 Alkyl, C1-4Alkoxy, C3-4Alkenyl oxygroup or C3-4Alkynyl oxygroup.
10. according to claim 1 to compound described in any one of 4 or claim 9, wherein Z expression-N (R10)R11, wherein R10It is hydrogen, C1-4Alkyl, C1-4Halogenated alkyl, cyano C1-2Alkyl, hydroxyl C2-4Alkyl, C1-2Alkoxy C2-4Alkyl, C1-2Alkyl halide Oxygroup C1-2Alkyl, C3-4Alkenyl, C3-4Alkynyl, formoxyl, C1-2Alkyl-carbonyl, C1-2Alkyl-carbonyl C1-2Alkyl, C1-2Alkoxy carbonyl Base C1-2Alkyl or C1-2Alkyl carbonyl epoxide C1-2Alkyl；Or
R10It is C3-6Naphthenic base or C3-6Naphthenic base C1-2Alkyl；
Wherein work as R10It is C3-6Naphthenic base or C3-6Naphthenic base C1-2When alkyl, the C3-6Naphthenic base motif is optionally taken by 1 or 2 Replace for base, the substituent group can it is identical or or it is different, be selected from R12；
R12Indicate cyano, fluorine, chlorine, bromine, methyl or methoxy；And wherein work as R10It is substituted C3-6Naphthenic base or heterocycle When, these rings can contain carbonyl (C=O) group；And
R11Indicate hydrogen, hydroxyl, C1-4Alkyl, C1-2Halogenated alkyl, C3-4Alkenyl, C3-4Alkynyl, C3-4Naphthenic base, C3-4Naphthenic base C1-2 Alkyl or C1-4Alkoxy.
11. compound according to any one of claim 1 to 10, wherein n is 0 or 1.
12. a kind of agrochemical composition, the agrochemical composition include effective fungicidal amount according to claim 1 extremely With the compound of formula (I) described in any one of 11.
13. composition according to claim 12, the composition further includes at least one other active constituent And/or acceptable diluent or carrier in agrochemicals.
14. a kind of method that control or prevention phytopathogenic microorganisms infect useful plant, wherein by effective fungicidal amount Compound according to any one of claim 1 to 11 with formula (I) or comprising this compound as active constituent Composition is applied to the plant, its part or its place.
15. purposes of the compound according to any one of claim 1 to 11 with formula (I) as fungicide.