Pesticidally active cyclopropyl methyl amide derivatives

Patent metadata

Field	Value
Publication number	US-11388902-B2
Application number	US-201816496195-A
Country	US
Kind code	B2
Filing date	Mar 22, 2018
Priority date	Mar 22, 2017
Publication date	Jul 19, 2022
Grant date	Jul 19, 2022

Abstract

The present invention relates to 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; 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 , independently of one another, are C—H, C—R 5 or nitrogen;
R 1 is 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 or C 1 -C 8 alkoxycarbonylC 1 -C 8 alkylaminoC 1 -C 8 alkyl, wherein each alkyl or alkoxy group may be optionally substituted with from one to three halogen atoms;
R 2 is cyano, C(S)NH 2 or C(O)NH 2 ;
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 6 is hydrogen or C 1 -C 8 alkyl; and
R 7 is independently halogen, cyano, nitro, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy;
and agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds.

2. A compound of formula (I) according to claim 1 , wherein R 1 is C 1 -C 8 alkoxy-C 1 -C 8 alkyl, C 1 -C 8 alkoxycarbonyl or C 1 -C 8 alkylcarbonyloxyC 1 -C 8 alkyl.

3. A compound of formula (I) according to claim 2 , wherein R 1 is methoxymethyl, ethoxymethyl, methoxycarbonyl, ethoxycarbonyl, methylcarbonyloxymethyl, 1-methylethylcarbonyloxymethyl or 1,1-dimethylethylcarbonyloxymethyl.

4. A compound of formula (I) according to claim 1 , wherein R 2 is cyano.

5. A compound of formula (I) according to claim 1 , wherein R 2 is C(S)NH 2 or C(O)NH 2 .

6. A compound of formula (I) according to claim 1 , wherein R 3 is C 1 -C 4 haloalkyl.

7. A compound of formula (I) according to claim 1 , wherein R 4 is aryl, aryl substituted by one to three R 7 , 5-6 membered heteroaryl or 5-6 membered heteroaryl substituted by one to three R 7 .

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

9. A compound of formula (I) according to claim 1 , wherein R 7 is independently halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy.

10. A compound of formula (I) according to claim 1 , wherein R 6 is hydrogen.

11. A compound of formula (Int-II)

A 1 , A 2 , A 3 and A 4 , independently of one another, are C—H, C—R 5 or nitrogen;
R 1 is hydrogen, 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 or C 1 -C 8 alkoxycarbonylC 1 -C 8 alkylaminoC 1 -C 8 alkyl, wherein each alkyl or alkoxy group may be optionally substituted with from one to three halogen atoms or with a cyano group;
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 6 is hydrogen or C 1 -C 8 alkyl;
R 2 is cyano, C(S)NH 2 , C(O)OH or C(O)NH 2 ; X c is CH 2 -halogen, CH═C(R 3 )R 4 or CH 2 C(OH)(R 3 )R 4
wherein R 3 and R 4 are as defined under formula (I) in claim 1 ; and a salt or N-oxide of a compound of formula (Int-II).

12. A compound of formula (Int-III)

A 1 , A 2 , A 3 and A 4 , independently of one another, are C—H, C—R 5 or nitrogen;
R 1 is hydrogen, 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 or C 1 -C 8 alkoxycarbonylC 1 -C 8 alkylaminoC 1 -C 8 alkyl, wherein each alkyl or alkoxy group may be optionally substituted with from one to three halogen atoms or with a cyano group;
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 6 is hydrogen or C 1 -C 8 alkyl; and
R 7 is independently halogen, cyano, nitro, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy;
and a salt or N-oxide of the compound of formula (Int-III).

13. A pesticidal composition, which comprises at least one compound of formula (I) according to claim 1 or, where appropriate, a tautomer thereof, in each case in free form or in agrochemically utilizable salt form, as active ingredient and at least one auxiliary.

14. A method for controlling pests, which comprises applying a composition according to claim 13 to the pests or their environment with the exception of a method for treatment of the human or animal body by surgery or therapy and diagnostic methods practised on the human or animal body.

15. A method for the protection of seeds from the attack by pests, which comprises treating the seeds or the site, where the seeds are planted, with a composition according to claim 13 .

16. A compound of formula (I),

wherein
A 1 , A 2 , A 3 and A 4 , independently of one another, are C—H, C—R 5 or nitrogen;
R 1 is hydrogen, 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,

Assignees

• Syngenta Participations Ag

Inventors

• Cassayre Jérôme Yves
• El Qacemi Myriem
• Pitterna Thomas
• STOLLER ANDRé

Classifications

• C07D261/04 Primary

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

• A61P33/00

  Antiparasitic agents · CPC title

• A01N53/00

  Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof · CPC title

• C07D413/04

  directly linked by a ring-member-to-ring-member bond · CPC title