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US 8,084,474 B2Granted
Insecticides
AssigneeSyngenta Crop Protection AG
InventorsMichel Muehlebach, Andre Jeanguenat, Roger Graham Hall
Life of this patent
Estimating the term…
Abstract
Compounds of formula (I) wherein the substituents are as defined in claim (1), and the agrochemically acceptable salts and all stereoisomers and tautomeric forms of the compounds of formula (I) can be used as agrochemical active ingredients and can be prepared in a manner known per se.
Claims19
A compound of formula I
- wherein
- or D is a group
- R4, R4′, R10, R17, and R19 independently from each other, are hydrogen, C1-C6alkyl, C3-C6cycloalkyl, C1-C6haloalkyl, halogen, cyano, C1-C4alkoxy, C1-C4haloalkoxy, C2-C4alkoxycarbonyl, C1-C4alkylthio, C1-C4haloalkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4haloalkylsulfinyl or C1-C4haloalkylsulfonyl;
- R5, R6, R8, R11, R12, R15, R16 and R18 independently from each other, are C1-C6alkyl, or C1-C6alkyl mono-, di- or trisubstituted by halogen, cyano, nitro, hydroxy, C1-C4alkoxy, C2-C4alkoxycarbonyl, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4alkylamino, C2-C4dialkylamino or C3-C6cycloalkylamino;
- or are phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl;
- or are phenyl, 2-pyridyl, 3-pyridyl or 4-pyridyl mono-, di- or trisubstituted by C1-C6alkyl, C3-C6cycloalkyl, C1-C6haloalkyl, halogen, cyano, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4haloalkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4haloalkylsulfinyl or C1-C4haloalkylsulfonyl;
- R7, R9, R13 and R14 independently from each other, are hydrogen, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C3-C6alkenyl or C3-C6haloalkenyl;
- each R1 independently is halogen, nitro, cyano, hydroxy, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C1-C6haloalkyl, C2-C6haloalkenyl, C2-C6haloalkynyl, C3-C6halocycloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4haloalkylthio, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4alkylamino, C2-C4dialkylamino, C3-C6cycloalkylamino, C1-C6alkyl-C3-C6cycloalkylamino, C2-C4alkylcarbonyl, C2-C6alkoxycarbonyl, C2-C6alkylaminocarbonyl, C3-C6dialkylaminocarbonyl, C2-C6alkoxycarbonyloxy, C2-C6alkylaminocarbonyloxy, C3-C6dialkylaminocarbonyloxy or C3-C6-trialkylsilyl, phenyl, benzyl or phenoxy, or phenyl, benzyl or phenoxy mono-, di- or trisubstituted by halogen, cyano, nitro, halogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C1-C6haloalkyl, C2-C6haloalkenyl, C2-C6haloalkynyl, C3-C6halocycloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4haloalkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4alkylamino, C2-C4dialkylamino, C3-C6cycloalkylamino, C1-C6alkyl-C3-C6cycloalkylamino, C2-C4alkylcarbonyl, C2-C6alkoxycarbonyl, C2-C6alkylaminocarbonyl, C3-C6dialkylaminocarbonyl, C2-C6alkoxycarbonyloxy, C2-C6alkylaminocarbonyloxy, C3-C6dialkylaminocarbonyloxy or C3-C6-trialkylsilyl;
- n is 0, 1, 2 or 3;
- each of R2 and R3, which may be the same or different, represents hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl or C3-C8cycloalkyl;
- or C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl or C3-C8cycloalkyl substituted by one or more substituents selected from halogen nitro, cyano, hydroxy, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4haloalkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4alkylamino, C2-C4dialkylamino, C3-C6cycloalkylamino and C1-C6alkyl-C3-C6cycloalkylamino;
- each of E1 and E2, which may be the same or different, represents oxygen or sulfur;
- A is oxygen, sulfur, SO, SO2, S(O)p═N—R, C═N—OR36, N—R0, C═O or P(X)t—R33;
- R33 is hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6haloalkyl, C1-C6alkoxy, hydroxy, C3-C6cycloalkyl, C3-C6cycloalkyl-C1-C6alkyl, benzyl or phenyl;
- where phenyl and benzyl for their part may be mono- di- or trisubstituted by C1-C6alkyl, C1-C6haloalkyl, halogen, cyano or nitro;
- or R33 is O−Na+, O−Li+ or O−K+;
- R36 is hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6haloalkyl, C2-C6haloalkenyl, C2-C6haloalkynyl, C1-C6alkoxy-C1-C6alkyl, C1-C6haloalkoxy-C1-C6alkyl or benzyl;
- X is oxygen or sulfur;
- p is 0 or 1;
- t is 0 or 1;
- each of R34 and R35, which may be the same or different, represents hydrogen, COOH, halogen, nitro, cyano, hydroxy, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6alkynyl, C2-C6haloalkenyl, C2-C6haloalkynyl, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylthio, C1-C6haloalkylsulfinyl, C1-C6haloalkylsulfonyl, C1-C6alkoxycarbonyl, C1-C6alkylcarbonyl, C3-C6alkylaminocarbonyl, C3-C6dialkylaminocarbonyl, C1-C6alkoxy-C1-C6alkyl, C1-C6haloalkoxy-C1-C6alkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylamino, C2-C6dialkylamino, C3-C6-trialkylsilyl, benzyl or phenyl;
- where phenyl and benzyl for their part may be mono- di- or trisubstituted by C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, halogen, cyano, hydroxyl or nitro;
- m is 0, 1, 2, 3 or 4;
- R is hydrogen, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C3-C6halocycloalkyl, C1-C6alkylthio, C1-C6haloalkylthio, C1-C6alkoxy-C1-C6alkyl or C1-C6haloalkoxy-C1-C6alkyl;
- or R is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C3-C6halocycloalkyl, C1-C6alkylthio, C1-C6haloalkylthio, C1-C6alkoxy-C1-C6alkyl or C1-C6haloalkoxy-C1-C6alkyl substituted by C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C3-C6halocycloalkyl, C1-C6alkoxy, or C1-C6haloalkoxy;
- or R is cyano, nitro, —C(O)R26, —C(O)OR27, —CONR28R29, SO2R30 or —P(O)(OR31)(OR32);
- R0 is hydrogen, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C3-C6halocycloalkyl, C1-C6alkylthio, C1-C6haloalkylthio, C1-C6alkoxy-C1-C6alkyl or C1-C6haloalkoxy-C1-C6alkyl;
- or R0 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C3-C6halocycloalkyl, C1-C6alkylthio, C1-C6haloalkylthio, C1-C6alkoxy-C1-C6alkyl or C1-C6haloalkoxy-C1-C6alkyl substituted by C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C3-C6halocycloalkyl, C1-C6alkoxy, or C1-C6haloalkoxy;
- or R0 is cyano, nitro, —C(O)R026, —C(O)OR027, —CONR028R029, —SO2R030 or —P(O)(OR031)(OR032);
- or R0 is phenyl or benzyl, or phenyl or benzyl mono-, di- or trisubstituted by substituents selected from C1-C6alkyl, C3-C6cycloalkyl, C1-C6haloalkyl, halogen, cyano, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4haloalkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4haloalkylsulfinyl and C1-C4haloalkylsulfonyl;
- each of R26 and R026, which may be the same or different, represents hydrogen, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C3-C6halocycloalkyl, C1-C6alkylthio, C1-C6haloalkylthio, C1-C6alkoxycarbonyl, C1-C6alkylcarbonyl or C1-C6alkoxy-C1-C6alkyl;
- or C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C3-C6halocycloalkyl, C1-C6alkylthio, C1-C6haloalkylthio, C1-C6alkoxycarbonyl, C1-C6alkylcarbonyl or C1-C6alkoxy-C1-C6alkyl substituted by C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C3-C6halocycloalkyl, C1-C6alkoxy, or C1-C6haloalkoxy;
- each of R27, R28, R29, R30, R31, R32, R027, R028, R029, R030, R031 and R032 which may be the same or different, represents C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl or C3-C6halocycloalkyl;
- or C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl or C3-C6halocycloalkyl substituted by C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C3-C6halocycloalkyl, C1-C6alkoxy or C1-C6haloalkoxy;
- with the proviso that E1 or E2 is sulfur if A is oxygen, sulfur or N—R0, wherein R0 is hydrogen, C1-C3alkyl, C1-C3haloalkyl, C2-C4alkylcarbonyl, C2-C4haloalkylcarbonyl, C2-C4alkoxycarbonyl or C1-C3alkylsulfonyl;
- and agronomically acceptable salts/isomers/diastereomers/enantiomers/tautomers/N-oxides of those compounds said compound.
33 more elements
Dependencies are inferred from the claim text.