Insecticidal compounds

Patent metadata

Field	Value
Publication number	US-11104671-B2
Application number	US-201816496758-A
Country	US
Kind code	B2
Filing date	Mar 22, 2018
Priority date	Mar 23, 2017
Publication date	Aug 31, 2021
Grant date	Aug 31, 2021

Abstract

The present invention relates to compounds of formula (I) wherein A 1 , A 2 , A 3 , A 4 , R 1 , R 2 , R 3 , R 4 and n are as defined in claim 1 ; or a tautomer, isomer, enantiomer, salt or N-oxide thereof; to intermediates for preparing compounds of formula (I), to compositions comprising them and to methods of using them to combat and control insect, acarine, nematode and mollusc pests.

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 nitrogen;
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, 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;
R 2 is C 1 -C 8 alkyl, C 1 -C 8 alkyl substituted by one to three R 6a , C 1 -C 8 haloalkyl, C 1 -C 8 haloalkyl substituted by one to three R 6a , C 3 -C 8 cycloalkyl, 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 , 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 , C 3 -C 8 cycloalkyl-C 1 -C 8 haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkenyl substituted by one to three R 6a , C 2 -C 8 haloalkenyl, 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, 5-6 membered heteroaryl-C 1 -C 4 alkyl wherein the heteroaryl moiety is substituted by one to three R 7 , —N(R 8 )(R 9 ), —OR 10 or halogen;
R 3 is C 1 -C 8 haloalkyl;
R 4 is aryl, aryl substituted by one to three R 7 , heteroaryl or heteroaryl substituted by one to three R 7 ;
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 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 1 -C 8 haloalkyl, C 2 -C 8 haloalkenyl, hydroxy, C 1 -C 8 alkoxy, C 3 -C 8 alkenyloxy, C 3 -C 8 alkynyloxy, or C 1 -C 8 haloalkoxy, provided that at least one of R 5a and R 5b is not hydrogen;
R 6a is independently cyano, nitro, amino, C 1 -C 8 alkylamino, N,N—C 1 -C 8 dialkylamino, hydroxy, C 1 -C 8 alkoxy, or C 1 -C 8 haloalkoxy;
R 6b is independently halogen, cyano, nitro, oxo, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, amino, C 1 -C 8 alkylamino, N,N—C 1 -C 8 dialkylamino, hydroxyl, C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, phenyl, phenyl substituted by one to three R 7 , 5-6 membered heteroaryl, or 5-6 membered heteroaryl substituted by one to three R 7 ;
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, cyano-C 1 -C 8 alkyl, C 1 -C 8 alkyl, C 1 -C 8 alkyl substituted by one to three R 6a , C 2 -C 8 alkenyl, C 2 -C 8 alkenyl 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, C 1 -C 8 haloalkyl substituted by one to three R 6a , C 3 -C 8 cycloalkyl, 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 , 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 , C 3 -C 8 cycloalkyl-C 1 -C 8 haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkenyl substituted by one to three R 6a , C 2 -C 8 haloalkenyl, 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, 5-6 membered heteroaryl-C 1 -C 4 alkyl wherein the heteroaryl moiety is substituted by one to three R 7 , —S(O)R 10 , —S(O) 2 R 10 , COR 10 , COOR 10 , 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, C 1 -C 8 alkyl, C 1 -C 8 alkyl substituted by one to three R 6a , C 1 -C 8 haloalkyl, C 1 -C 8 haloalkyl substituted by one to three R 6a , C 3 -C 8 cycloalkyl, 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 , 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 , C 3 -C 8 cycloalkyl-C 1 -C 8 haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkenyl substituted by one to three R 6a , C 2 -C 8 haloalkenyl, 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 ;
n is 1 or 2;
provided that if B 1 -B 2 -B 3 -B 4 is —CH 2 —C═N—O— then the only meaning of R 5 is that two R 5 on adjacent carbon atoms together form a —CH 2 —CH 2 —CH 2 — bridge, a —CH(OH)—CH 2 —CH 2 — bridge or a —C(O)—CH 2 —CH 2 — bridge;
and an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer and N-oxide thereof.

2. The compound according to claim 1 , wherein A 1 is CR 5 and A 2 , A 3 and A 4 are each CH.

3. The compound according to claim 1 , wherein R 1 is hydrogen, C 1 -C 8 alkyl, C 1 -C 8 alkylcarbonyl- or C 1 -C 8 alkoxycarbonyl-.

4. The compound of formula (I) according to claim 1 , wherein R 1 is 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.

5. The compound of formula (I) according to claim 4 , wherein R 1 is C 1 -C 8 alkoxy-C 1 -C 8 alkyl, or C 1 -C 8 alkoxycarbonyl.

6. The compound of formula (I) according t

Assignees

• Syngenta Participations Ag

Inventors

• Cassayre Jérôme Yves
• El Qacemi Myriem
• STOLLER ANDRé

Classifications

• A01N43/80

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

• C07D413/12 Primary

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

• C07D413/14

  containing three or more hetero rings · CPC title

• C07D417/12

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