Pesticidally active pyridazinone compounds
AssigneeSyngenta Crop Protection AG
InventorsJagadeesh Prathap KILARU, Mangala PHADTE, Simone BERARDOZZI, Roger Graham HALL, André JEANGUENAT, Thomas PITTERNA, Matthias WEISS, Michel MUEHLEBACH
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Abstract
Compounds of formula (I) where Q is Qa or Qb; and R4 is R4a or R4b, and 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.
Claims21
A compound of the formula (I)
- wherein:
- A1, A2 and A3 are, independently from each other, N or CRY;
- or
- A1=A2-A3, taken together, are NR—C(═X)—N;
- wherein X is O or S;
- A4 and A5 are, independently from each other, N or CRY;
- Q is
- where the staggered line represents the connection of Q to the rest of compound of the formula (I);
- R is hydrogen, C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, or C1-C3haloalkoxy;
- R1 is hydrogen, C1-C6alkyl, C1-C6cyanoalkyl, aminocarbonylC1-C6alkyl, hydroxycarbonylC1-C6alkyl, C1-C6nitroalkyl, trimethylsilaneC1-C6alkyl, C1-C3alkoxy-C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C3-C4cycloalkylC1-C2alkyl-, C3-C4cycloalkylC1-C2alkyl- wherein the C3-C4cycloalkyl group is substituted with 1 or 2 halogen atoms, oxetan-3-yl-CH2—, C1-C6alkylcarbonyl, C1-C6alkoxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, benzyl or benzyl substituted with 1 to 3 substituents independently selected from halogen, C1-C6alkoxy and C1-C6haloalkyl;
- R2a and R2b are each independently selected from hydrogen, C1-C3alkyl, C1-C3haloalkyl, C1-C3haloalkylsulfanyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, NO2, SF5, CN, C(O)NH2, C(O)OH, C(S)NH2, C3-C6cycloalkyl, C3-C6cycloalkyl substituted with one to three substituents independently selected from Rx, C3-C6cycloalkylcarbonyl, phenyl, phenyl substituted with one to three substituents independently selected from Rx, heteroaryl, heteroaryl substituted with one to three substituents independently selected from Rx, OR6, piperidin-2-one-1-yl, piperidin-2-one-1-yl substituted with one to two substituents independently selected from Rx, pyridin-2-one-1-yl, pyridin-2-one-1-yl substituted with one to two substituents independently selected from Rx, azetidin-1-yl, azetidin-1-yl substituted with one to two substituents independently selected from Rx, pyrrolidin-1-yl, pyrrolidin-1-yl substituted with one to two substituents independently selected from Rx, C3-C6cycloalkylC1-C4alkyl, C3-C6cycloalkylC1-C4alkyl substituted with one to two substituents independently selected from Rz, C3-C6cycloalkylC1-C3alkoxy, C3-C6cycloalkylC1-C3alkoxy substituted with one to two substituents independently selected from Rx, C1-C5cyanoalkyl, C1-C5cyanoalkoxy, C1-C4alkylsulfanyl, C1-C4alkylsulfanyl substituted with one to three substituents independently selected from Rx, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl substituted with one to three substituents independently selected from Rx, C1-C4alkylsulfinyl, and C1-C4alkylsulfinyl substituted with one to three substituents independently selected from Rx;
- R3 is C1-C3alkyl or C1-C3haloalkyl;
- R4 is
- where the staggered line represents the connection of R4 to Qa or Qb;
- A14, A24, and A34 are, independently of each other, N or CH;
- R4c is C1-C3alkyl, C1-C3haloalkyl, allyl, propargyl, or C3-C6cycloalkylC1-C4alkyl;
- R5 is hydrogen, C1-C3alkyl, C1-C3haloalkyl, C3-C4cycloalkyl, C1-C3alkoxy, C3-C4alkoxyC(O)—, (C1-C3alkoxy)2CH—, halogen, CN, NH2C(O), amino (i.e NH2), (C1-C3alkyl)amino, di(C1-C3alkyl)amino, hydroxy, C3-C4halocycloalkyl, C3-C4cyanocycloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C1-C4haloalkylsulfanyl, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl, C1-C4alkylsulfanyl, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C3alkoxy-C1-C3alkyl, C1-C3alkoxy-C1-C3alkoxy-C1-C3alkyl, (C1-C3alkyl)sulfonylamino, (C1-C3alkyl)sulfonyl(C1-C3alkyl)amino, (C1-C3alkyl)NHC(O), (C1-C3alkyl)2NC(O), (C1-C3cycloalkyl)NHC(O), (C1-C3cycloalkyl)(C1-C3alkyl)NC(O), (C1-C3alkyl)C(O)(C1-C3alkyl)N, (C1-C3alkyl)C(O)NH, (C1-C3alkyl)C(O), (C1-C3alkoxy)C(O), HC(O), diphenylmethanimine, C1-C3haloalkoxy, phenyl, or a 5-membered heteroaromatic ring;
- or
- R5 is phenyl substituted with one to three substituents selected from C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C3-C4cycloalkyl, halogen, CN and hydroxyl;
- or
- R5 is a 5-membered heteroaromatic ring substituted with one to three substituents selected from C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C3-C4cycloalkyl, halogen, CN and hydroxyl;
- R5a and R5b are, independently of each other, selected from hydrogen, halogen, CN, C1-C3alkyl, C1-C3haloalkyl, C3-C4cycloalkyl, C1-C3alkoxy, and C1-C3haloalkoxy;
- R6 is phenyl, benzyl, heteroaryl, or C3-C6 cycloalkyl;
- or
- R6 is phenyl, benzyl, heteroaryl, or C3-C6 cycloalkyl, each of which, independent of each other, is substituted with one to three substituents independently selected from Rx;
- Rx is independently selected from halogen, C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, NO2, SF5, CN, C(O)NH2, C(S)NH2, C1-C4haloalkylsulfanyl, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl, C1-C4alkylsulfanyl, C1-C4alkylsulfinyl and C1-C4alkylsulfonyl;
- RY is selected from hydrogen, C1-C3 alkyl, C1-C3 haloalkyl, hydroxy, C1-C3 alkoxy, C1-C3 haloalkoxy, halogen, CN and cyclopropyl;
- and
- RZ is selected from oxo, halogen, C1-C3 alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy and CN;
- or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer and N-oxide of the compound of formula I.
The compound according to wherein R4c is methyl, ethyl, propyl, difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, allyl, propargyl, cyclopropylmethyl, cyclobutylmethyl, 2-cyclpropylethyl, or 3-cyclopropylpropyl.
Dependencies are inferred from the claim text.