Isoxazoline-substituted benzamides and analogues as insecticides

Patent metadata

Field	Value
Publication number	US-10499642-B2
Application number	US-201615762498-A
Country	US
Kind code	B2
Filing date	Sep 22, 2016
Priority date	Sep 23, 2015
Publication date	Dec 10, 2019
Grant date	Dec 10, 2019

Abstract

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

First claim

The invention 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;
R 1 is hydrogen, formyl, C 1 -C 8 alkyl, C 1 -C 8 alkylcarbonyl-, C 1 -C 8 alkoxy, C 1 -C 8 alkoxy-C 1 -C 8 alkyl or C 1 -C 8 alkoxycarbonyl, 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 ;
R 2 is hydrogen, halogen, cyano, —NH(R 8 ), —N(R 8 )(R 9 ), —OR 10 , —SR 10 , —S(O)R 10 , —S(O) 2 R 10 , COR M , COOR 10 , 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 , or 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 ;
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 ;
each 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 or a —N═CH—CH═CH— bridge;
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 halo alkoxy, C 1 -C 4 alkylthio or tri-(C 1 -C 4 alkyl)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;
each 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 ; and
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 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 , or 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
an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer and N-oxide thereof.

2. The compound of 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. The compound of 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, di-C 1 -C 4 alkylamino, C 1 -C 4 alkylthio, or C 1 -C 4 alkyloxycarbonyl.

4. The compound of claim 1 , wherein R 1 is hydrogen, formyl, C 1 -C 8 alkyl, C 1 -C 8 alkylcarbonyl- or C 1 -C 8 alkoxycarbonyl-.

5. The compound of claim 1 , wherein R 3 is C 1 -C 4 haloalkyl.

6. The compound of claim 1 , wherein
R 4 is phenyl or phenyl substituted by one to three R 6b ; and
each R 6b independently is halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, or C 1 -C 4 haloalkoxy.

7. The compound of claim 6 , wherein R 6b is bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy, or trifluoromethoxy.

8. The compound of claim 1 , wherein at least two of A 1 , A 2 , A 3 and A 4 is C—H.

9. The compound of claim 1 , wherein R 2 is halogen, cyano, —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 ,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 , or 5-6 membered heteroar

Assignees

• Syngenta Participations Ag

Inventors

• O'Sullivan Anthony Cornelius
• El Qacemi Myriem
• Cassayre Jérôme Yves
• Pitterna Thomas
• STOLLER ANDRé

Classifications

• A61P33/14

  Ectoparasiticides, e.g. scabicides · CPC title

• A61P33/10

  Anthelmintics · CPC title

• C07D413/14

  containing three or more hetero rings · 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