Insecticidal compounds

Patent metadata

Field	Value
Publication number	US-11213032-B2
Application number	US-201816496679-A
Country	US
Kind code	B2
Filing date	Mar 22, 2018
Priority date	Mar 23, 2017
Publication date	Jan 4, 2022
Grant date	Jan 4, 2022

Abstract

Compounds of formula (I) wherein the substituents are as defined in claim 1 , and the agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds, and their uses as insecticides.

First claim

What is claimed is:

1. A compound of formula (I),

Wherein
A 1 , A 2 , A 3 and A 4 are, independently of one another, C—H, C—R 5 or N;
B 1 —B 2 —B 3 —B 4 is —C(R 5a R 5b )—C═N—O—, —CH 2 —C═N—CH 2 —, —CH 2 —C═CH 2 —S—, —CH 2 —C═N—S—, —CH 2 —N—CH 2 —CH 2 —, —CH 2 —C═CH—O—, —CH(OH)—N—CH 2 —CH 2 —, —C(O)—N—CH 2 —CH 2 —, —CH 2 —C═N—O— or —CH═C—CH 2 —O—;
R 1 is hydrogen, formyl, C 1 -C 8 alkyl, C 1 -C 8 alkylcarbonyl-, C 3 -C 6 cycloalkylcarbonyl, C 1 -C 8 alkoxy, C 1 -C 8 alkoxy-C 1 -C 8 alkyl, C 1 -C 8 alkoxycarbonyl, C 1 -C 8 alkylcarbonyloxyC 1 -C 8 alkyl, C 1 -C 8 alkoxycarbonylsulfanyl, C 1 -C 8 alkylaminocarbonyloxyC 1 -C 8 alkyl, C 1 -C 8 dialkylaminocarbonyloxyC 1 -C 8 alkyl, C 1 -C 8 alkylaminocarbonylC 1 -C 8 alkyl, C 1 -C 8 dialkylaminocarbonylC 1 -C 8 alkyl, C 1 -C 8 alkoxycarbonylC 1 -C 8 alkylaminoC 1 -C 8 alkyl, phenyl-C 1 -C 8 alkoxycarbonyl, phenyl-C 1 -C 4 alkyl or phenyl-C 1 -C 4 alkyl wherein the phenyl moiety is substituted by one to three R 7 , wherein each alkyl or alkoxy group may be optionally substituted with from one to three halogen atoms or with a cyano group;
R 2 is hydrogen, halogen, cyano, C 1 -C 8 alkyl or C 1 -C 8 alkyl substituted by one to three R 6a , C 1 -C 8 haloalkyl or C 1 -C 8 haloalkyl substituted by one to three R 6a , C 3 -C 8 cycloalkyl or C 3 -C 8 cycloalkyl substituted by one to three R 6b , C 3 -C 8 cycloalkyl where one carbon atom is replaced by O, S, S(O) or SO 2 , or C 3 -C 8 cycloalkyl-C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl-C 1 -C 8 alkyl where one carbon atom in the cycloalkyl group is replaced by O, S, S(O) or SO 2 , or C 3 -C 8 cycloalkyl-C 1 -C 8 haloalkyl, C 2 -C 8 alkenyl or C 2 -C 8 alkenyl substituted by one to three R 6a , C 2 -C 8 haloalkenyl or C 2 -C 8 haloalkenyl substituted by one to three R 6a , C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, phenyl, phenyl substituted by one to three R 7 , phenyl-C 1 -C 4 alkyl, phenyl-C 1 -C 4 alkyl wherein the phenyl moiety is substituted by one to three R 7 , 5-6 membered heteroaryl, 5-6 membered heteroaryl substituted by one to three R 7 , 5-6 membered heteroaryl-C 1 -C 4 alkyl or 5-6 membered heteroaryl-C 1 -C 4 alkyl wherein the heteroaryl moiety is substituted by one to three R 7 , —NH(R 8 ), —N(R 8 )(R 9 ), —OR 10 , —SR 10 , —S(O)R 10 , —S(O) 2 R 10 , COR 10 , COOR 10 ;
R 3 is C 1 -C 8 haloalkyl;
R 4 is phenyl or phenyl substituted by one to three R 6b or pyridine or pyridine substituted by one to three R 6b ;
R 5 is independently halogen, cyano, nitro, C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl, C 1 -C 8 haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, or C 1 -C 8 alkoxycarbonyl-, or two R 5 on adjacent carbon atoms together form a —CH═CH—CH═CH— bridge, a —CH 2 —CH 2 —CH 2 — bridge, a —CH(OH)—CH 2 —CH 2 — bridge, a —C(O)—CH 2 —CH 2 — bridge, or a —N═CH—CH═CH— bridge;
R 5a and R 5b are, independently of each other, hydrogen, cyano, halogen, hydroxyl, C 1 -C 8 alkyl-, C 1 -C 8 alkyl-substituted by one to five R 6a , C 1 -C 8 alkylthio-, C 1 -C 8 haloalkylthio-, C 1 -C 8 alkylsulfinyl-, C 1 -C 8 haloalkylsulfinyl-, C 1 -C 8 alkylsulfonyl-, C 1 -C 8 haloalkylsulfonyl-, arylthio- or arylthio- wherein the aryl moiety is substituted by one to five R 7 , arylsulfinyl- or arylsulfinyl- wherein the aryl moiety is substituted by one to five R 7 , arylsulfonyl- or arylsulfonyl- wherein the aryl moiety is substituted by one to five R 7 , heterocyclylthio- or heterocyclylthio- wherein the heterocyclyl moiety is substituted by one to five R 7 , heterocyclylsulfinyl- or heterocyclylsulfinyl- wherein the heterocyclyl moiety is substituted by one to five R 7 , or heterocyclylsulfonyl- or heterocyclylsulfonyl- wherein the heterocyclyl moiety is substituted by one to five R 7 , C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkenyl, C 1 -C 8 alkoxy, or C 1 -C 8 haloalkoxy, provided that at least one of R 5a and R 5b is not hydrogen;
each R 6a is independently halogen, cyano, nitro, amino, hydroxy, oxo, C 1 -C 8 alkylamino, hydroxyimino, C 1 -C 8 alkyloxyimino, di-C 1 -C 8 alkylamino, C 1 -C 8 alkoxy, acetyloxy, formyloxy, C 1 -C 8 haloalkoxy, C 1 -C 4 alkylthio or (C 1 -C 4 alkyl) 0-3 silyl;
each R 6b is independently halogen, cyano, nitro, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, amino, C 1 -C 8 alkylamino, di-C 1 -C 8 alkylamino, hydroxyl, C 1 -C 4 alkylthio, C 1 -C 8 alkoxy or C 1 -C 8 haloalkoxy;
R 7 is independently halogen, cyano, nitro, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 1 -C 8 alkoxy, or C 1 -C 8 haloalkoxy;
R 8 and R 9 are independently hydrogen, cyano, C 1 -C 8 alkyl or C 1 -C 8 alkyl substituted by one to three R 6a , C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, C 1 -C 8 haloalkoxy substituted by one to three R 6a , C 1 -C 8 alkoxy substituted by one to three R 6a , C 1 -C 8 haloalkyl or C 1 -C 8 haloalkyl substituted by one to three R 6a , C 3 -C 8 cycloalkyl or C 3 -C 8 cycloalkyl substituted by one to three R 6b , C 3 -C 8 cycloalkyl where one carbon atom is replaced by O, S, S(O) or SO 2 , or C 3 -C 8 cycloalkyl-C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl-C 1 -C 8 alkyl where one carbon atom in the cycloalkyl group is replaced by O, S, S(O) or SO 2 , or C 3 -C 8 cycloalkyl-C 1 -C 8 haloalkyl, C 2 -C 8 alkenyl or C 2 -C 8 alkenyl substituted by one to three R 6a , C 2 -C 8 haloalkenyl or C 2 -C 8 haloalkenyl substituted by one to three R 6a , C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, phenyl, phenyl substituted by one to three R 7 , phenyl-C 1 -C 4 alkyl, phenyl-C 1 -C 4 alkyl wherein the phenyl moiety is substituted by one to three R 7 , 5-6 membered heteroaryl, 5-6 membered heteroaryl substituted by one to three R 7 , 5-6 membered heteroaryl-C 1 -C 4 alkyl or 5-6 membered heteroaryl-C 1 -C 4 alkyl wherein the heteroaryl moiety is substituted by one to three R 7 , or R 8 and R 9 together with the nitrogen atom can be linked through a C 3 -C 8 alkylene chain, a C 3 -C 8 alkylene chain substituted by one to three R 6b or a C 3 -C 8 alkylene chain, where one carbon atom is replaced by O, S, S(O) or SO 2 ;
R 10 is hydrogen, cyano, C 1 -C 8 alkyl or C 1 -C 8 alkyl substituted by one to three R 6a , C 1 -C 8 haloalkyl or C 1 -C 8 haloalkyl substituted by one to three R 6a , C 3 -C 8 cycloalkyl or C 3 -C 8 cycloalkyl substituted by one to three R 6b , C 3 -C 5 cycloalkyl where one carbon atom is replaced by O, S, S(O) or SO 2 , or C 3 -C 8 cycloalkyl-C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl-C 1 -C 8 alkyl where one carbon atom in the cycloalkyl group is replaced by O, S, S(O) or SO 2 , or C 3 -C 8 cycloalkyl-C 1 -C 8 haloalkyl, C 2 -C 8 alkenyl or C 2 -C 8 alkenyl substituted by one to three R 6a , C 2 -C 8 haloalkenyl or C 2 -C 8 haloalkenyl substituted by one to three R 6a , C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, phenyl, phenyl substituted by one to three R 7 , phenyl-C 1 -C 4 alkyl, phenyl-C 1 -C 4 alkyl wherein the phenyl moiety is substituted by one to three R 7 , 5-6 membered heteroaryl, 5-6 membered heteroaryl substituted by one to three R 7 , 5-6 membered heteroaryl-C 1 -C 4 alkyl or 5-6 membered heteroaryl-C 1 -C 4 alkyl wherein the heteroaryl moiety is substituted by one to three R 7 ;
and an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer and N-oxide thereof.

2. A compound of formula (I) according to claim 1 , wherein A 1 is C—R 5 ; A 2 is C—H; A 3 is C—H; and A 4 is C—H, wherein R 5 is halogen, cyano, nitro, C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl, C 1 -C 8 haloalkyl, or C 2 -C 8 alkenyl.

3. A compound of formula (I) according to claim 1 , wherein R 2 is halogen, C 1 -C 4 alkyl, C 3 -C 5 cycloalkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy o

Assignees

• Syngenta Participations Ag

Inventors

• El Qacemi Myriem
• Cassayre Jérôme Yves
• STOLLER ANDRé

Classifications

• C07D417/12 Primary

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D413/12

  linked by a chain containing hetero atoms as chain links · CPC title

• A01N43/80 Primary

  five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2 · CPC title

• C07D261/04

  having one double bond between ring members or between a ring member and a non-ring member · CPC title