Insecticidal compounds based on isoxazoline derivatives

Patent metadata

Field	Value
Publication number	US-11357231-B2
Application number	US-202017000978-A
Country	US
Kind code	B2
Filing date	Aug 24, 2020
Priority date	Dec 1, 2009
Publication date	Jun 14, 2022
Grant date	Jun 14, 2022

Abstract

Compounds of formula IIIwherein R1, R2, L, Y1, Y2, Y3, and Y4 are defined in claim 1.

First claim

The invention claimed is:

1. A compound of formula III

wherein
L is a C 1 -C 8 alkylene;
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 —; and
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;
wherein the compound is not

2. The compound according to claim 1 , wherein L is C 1 -C 4 alkylene.

3. The compound according to claim 1 , wherein L is methylene.

4. The compound according to claim 3 , 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.

5. The compound according to claim 4 , 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 .

6. The compound according to claim 5 , wherein each R 10 and R 8 is independently hydrogen, halogen, C 1 -C 4 alkyl, or C 1 -C 4 haloalkyl.

7. The compound according to claim 6 , wherein each R 10 is independently halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, or C 1 -C 4 haloalkoxy.

8. The compound according to claim 7 , wherein R 2 is hydrogen, C 1 -C 4 haloalkyl or C 1 -C 4 alkyl.

9. The compound according to claim 8 , wherein R 1 is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkylcarbonyl-, C 1 -C 4 alkoxy, C 1 -C 4 alkoxy-C 1 -C 4 alkyl or C 1 -C 4 alkoxycarbonyl-.

10. The compound according to claim 9 , wherein Y 4 is C═O.

11. The compound according to claim 10 , wherein Y 2 is O.

12. The 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 8 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, pyrazoyl, furanyl, thiophenyl, oxazolyl, isoxazolyl or thiazolyl.

13. The compound according to claim 12 , 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

Inventors

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

Classifications

• C07D417/12

  linked by a chain containing hetero atoms as chain links · 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

• 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

• C07D413/12 Primary

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