Insecticidal compounds based on isoxazoline derivatives

Patent metadata

Field	Value
Publication number	US-9609869-B2
Application number	US-201414258079-A
Country	US
Kind code	B2
Filing date	Apr 22, 2014
Priority date	Dec 1, 2009
Publication date	Apr 4, 2017
Grant date	Apr 4, 2017

Abstract

The present invention relates to compounds of formula (I):

wherein A 1 , A 2 , A 3 , A 4 , G 1 , L, Y 1 , Y 2 , Y 3 , Y 4 , R 1 , R 2 , R 3 and R 4 are as defined in claim 1 ; or a salt or N-oxide thereof.

Furthermore, the present invention relates 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 III

wherein
L is a single bond;
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 hydrogen, C 1 -C 8 haloalkyl or C 1 -C 8 alkyl;
Y 1 is CR 7 R 8 or C═O; and
Y 2 , Y 3 and Y 4 are independently CR 7 R 8 , C═O, N—R 9 , O, S, SO or SO 2 ;
wherein at least two adjacent ring atoms in the ring formed by Y 1 , Y 2 , Y 3 and Y 4 are heteroatoms;
each R 7 and R 8 is independently hydrogen, halogen, C 1 -C 8 alkyl, or C 1 -C 8 haloalkyl;
each R 9 is independently hydrogen, cyano, cyano-C 1 -C 8 alkyl, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 3 -C 8 cycloalkyl, 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 1 -C 8 hydroxyalkyl, C 1 -C 8 alkoxy-C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, phenyl, phenyl substituted by one to three R 10 , phenyl-C 1 -C 4 alkyl, phenyl-C 1 -C 4 alkyl wherein the phenyl moiety is substituted by one to three R 10 , 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 10 , or C 1 -C 4 alkyl-(C 1 -C 4 alkyl-O—N═)C—CH 2 —;
each R 10 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;

or a salt or N-oxide thereof; and
wherein the compound of formula III is not a compound of formula IIIA or IIIB

wherein R′ and R″ are hydrogen, ethyl, —CH 2 CH 2 OCH 3 , —CH 2 CH 2 OCH 2 CH 3 ,

—CH 2 CH 2 OH, or methyl; and
wherein R′ may not be

or —CH 2 CH 2 CH 2 CH 2 Cl.

2. A compound according to claim 1 , wherein Y 3 is N—R 9 and R 9 is cyano, cyano-C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkyl where one carbon atom is replaced by 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 S, S(O) or SO 2 , or 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, phenyl, phenyl substituted by one to three R 10 , phenyl-C 1 -C 4 alkyl, phenyl-C 1 -C 4 alkyl wherein the phenyl moiety is substituted by one to three R 10 , 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 10 , C 1 -C 4 alkyl-(C 1 -C 4 alkyl-O—N═)C—CH 2 —, and wherein heteroaryl refers to pyridazinyl, pyrimidinyl, pyrazinyl, pyrazolyl, furanyl, thiophenyl, oxazolyl, isoxazolyl or thiazolyl.

3. A compound according to claim 2 , wherein Y 3 is N—R 9 and R 9 is cyclopropyl, cyclobutyl, oxetanyl, thietanyl, trifluoroethyl, difluoroethyl, allyl, propargyl, cyanomethyl, benzyl, benzyl substituted by one to three R 10 .

Assignees

• Syngenta Crop Protection Llc
• Syngenta Crop Protection Llc

Inventors

• Cassayre Jerome Yves
• Renold Peter
• El Qacemi Myriem
• Pitterna Thomas
• Toueg Julie Clementine

Classifications

• A61P33/14

  Ectoparasiticides, e.g. scabicides · CPC title

• C07D261/04 Primary

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

• C07D419/12

  linked by a chain containing hetero atoms as chain links · 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