Insecticidal compounds based on N-arylsulfanylmethylcarboxamidearylthiosulfonamides derivatives

Patent metadata

Field	Value
Publication number	US-9675073-B2
Application number	US-201314442952-A
Country	US
Kind code	B2
Filing date	Nov 21, 2013
Priority date	Nov 21, 2012
Publication date	Jun 13, 2017
Grant date	Jun 13, 2017

Abstract

The present invention provides compounds of formula (I) wherein R 1 , R 2 , R 3 , R 4 , n, A 1 , A 2 , A 3 , A 4 , Y 1 , Y 2 and Y 3 are as defined in the claims. The invention also relates to processes and intermediates for preparing these compounds, to insecticidal, acaricidal, nematicidal and molluscicidal compositions comprising these compounds and to methods of using these compounds to control insect, acarine, nematode and mollusc pests.

First claim

The invention claimed is:

1. A compound of formula I

wherein
A 1 is C—R 5b ;
A 2 , A 3 and A 4 are independently of one another C—H;
Y 1 —Y 2 —Y 3 is —C═N—O—, —C═N—S—, —C═N—CH 2 —, —C═CH—O——N—CH 2 —CH 2 — or —C═CH—S;
n is 0, 1 or 2;
R 1 is hydrogen, C 1 -C 8 alkyl, C 1 -C 8 alkoxy, C 1 -C 8 alkylcarbonyl or C 1 -C 8 alkoxycarbonyl;
R 2 is hydrogen, C 1 -C 8 alkyl or C 1 -C 8 alkyl substituted by one to five R 6 , C 2 -C 8 alkenyl or C 2 -C 8 alkenyl substituted by one to five R 6 , C 2 -C 8 alkynyl or C 2 -C 8 alkynyl substituted by one to five R 6 , C 3 -C 10 cycloalkyl or C 3 -C 10 cycloalkyl substituted by one to five R 7 , aryl-C 1 -C 4 alkylene or aryl-C 1 -C 4 alkylene wherein the aryl moiety is substituted by one to five R 8 , heterocyclyl-C 1 -C 4 alkylene or heterocyclyl-C 1 -C 4 alkylene wherein the heterocyclyl moiety is substituted by one to five R 8 , aryl or aryl substituted by one to five R 8 , heterocyclyl or heterocyclyl substituted by one to five R 8 ;
or R 1 and R 2 together with the nitrogen atom to which they are bound form a 4- to 7-membered cycle containing carbon atoms as ring members and optionally containing one oxygen atom or one sulfur atom optionally oxidized as a ring member and wherein the cycle is optionally substituted by 1 to 5 groups independently selected from halogen, C 1 -C 4 alkyl and C 1 -C 4 alkoxy;
R 3 is C 1 -C 8 haloalkyl;
R 4 is aryl or aryl substituted by one to five R 9 , or heteroaryl or heteroaryl substituted by one to five R 9 ;
R 5b is halogen, C 1 -C 8 alkyl, 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 3 -C 10 cycloalkyl or C 3 -C 10 cycloalkyl substituted by one to five R 7 ;
each R 6 is independently halogen, cyano, nitro, hydroxy, C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, C 1 -C 8 alkylcarbonyl, C 1 -C 8 alkoxycarbonyl, mercapto, 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, or C 1 -C 8 haloalkylsulfonyl;
each R 7 is independently halogen, cyano, C 1 -C 8 alkyl or C 1 -C 8 haloalkyl;
each R 8 and R 9 is independently halogen, cyano, nitro, C 1 -C 8 alkyl, 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, hydroxy, C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, mercapto, 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, C 1 -C 8 alkylcarbonyl, C 1 -C 8 alkoxycarbonyl, aryl or aryl substituted by one to five R 10 or heterocyclyl or heterocyclyl substituted by one to five R 10 ;
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;
or a salt or N-oxide thereof.

2. A compound according to claim 1 , wherein Y 1 —Y 2 —Y 3 is —C═N—O—.

3. A compound according to claim 1 , wherein Y 1 —Y 2 —Y 3 is —C═N—CH 2 —.

4. A compound according to claim 1 , wherein Y 1 —Y 2 —Y 3 is —C═CH—O—.

5. A compound according to claim 1 , wherein Y 1 —Y 2 —Y 3 is —N—CH 2 —CH 2 —.

6. A compound according to claim 1 , wherein Y 1 —Y 2 —Y 3 is —C═N—S—.

7. A compound according to claim 1 , wherein Y 1 —Y 2 —Y 3 is —C═CH—S.

8. A compound according to claim 1 , wherein R 5b is halogen or methyl.

9. A compound according to claim 1 , wherein R 2 is C 1 -C 4 alkyl or C 1 -C 4 alkyl substituted by one to five groups independently selected from halogen, cyano, C 1 -C 4 alkoxy and C 1 -C 4 alkylthio, C 2 -C 4 alkenyl or C 2 -C 4 alkenyl substituted by one to five halogen, C 2 -C 4 alkynyl or C 2 -C 4 alkynyl substituted by one to five halogen, C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkyl substituted by one to five groups independently selected from halogen, cyano, methyl and halomethyl, phenyl-C 1 -C 2 alkylene or phenyl-C 1 -C 2 alkylene wherein the phenyl moiety is optionally substituted by one to three substituents independently selected from halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy and C 1 -C 4 haloalkoxy, pyridyl-C 1 -C 2 alkylene or pyridyl-C 1 -C 2 alkylene wherein the pyridyl moiety is optionally substituted by one to three substituents independently selected from halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy and C 1 -C 4 haloalkoxy, thietanyl, oxo-thietanyl, dioxo-thietanyl, oxetanyl, tetrahydrofuranyl, thietanyl-methyl, oxo-thietanyl-methyl, dioxo-thietanyl-methyl, and oxetanyl-methyl.

10. A compound according to claim 1 , wherein R 2 is C 1 -C 4 alkyl or C 1 -C 4 alkyl substituted by one to five groups independently selected from halogen, cyano, methoxy and methylthio, C 2 -C 4 alkenyl or C 2 -C 4 alkenyl substituted by one to five halogen, C 2 -C 4 alkynyl or C 2 -C 4 alkynyl substituted by one to five halogen, C 3 -C 4 cycloalkyl or C 3 -C 4 cycloalkyl substituted by one to five groups independently selected from halogen, cyano, methyl and halomethyl, pyridylmethyl or pyridylmethyl wherein the pyridyl moiety is substituted with one to four groups selected from halogen, cyano, methyl, halomethyl, methoxy and halomethoxy.

11. A compound according to claim 1 , wherein R 1 and R 2 together with the nitrogen atom to which they are bound form a 4- to 7-membered cycle containing carbon atoms as ring members and optionally containing one oxygen atom or one sulfur atom optionally oxidized as a ring member and wherein the cycle is optionally substituted by 1 to 5 groups independently selected from halogen, C 1 -C 4 alkyl and C 1 -C 4 alkoxy.

12. A compound according to claim 1 , wherein R 3 is chlorodifluoromethyl or trifluoromethyl.

13. A compound according to claim 1 , wherein R 4 is group A1

wherein X is C—R 12 or nitrogen and each R 12 is independently hydrogen, halogen or trihalomethyl, wherein at least two R 12 are not hydrogen.

14. A compound according to claim 1 , wherein A 1 is C—R 5b ; A 2 , A 3 and A 4 are C—H; Y 1 —Y 2 —Y 3 is —C═N—O—, —C═N—S—, —C═N—CH 2 —, —C═CH—O—N—CH 2 —CH 2 — or —C═CH—S; R 1 is hydrogen; R 2 is C 1 -C 4 alkyl or C 1 -C 4 alkyl substituted by one to five groups independently selected from halogen, cyano, methoxy and methylthio, C 2 -C 4 alkenyl or C 2 -C 4 alkenyl substituted by one to five halogen, C 2 -C 4 alkynyl or C 2 -C 4 alkynyl substituted by one to five halogen, C 3 -C 4 cycloalkyl or C 3 -C 4 cycloalkyl substituted by one to five groups independently selected from halogen, methyl and halomethyl, pyridylmethyl or pyridylmethyl wherein the pyridyl moiety is substituted with one to four groups selected from halogen, cyano, methyl, halomethyl, methoxy and halomethoxy; or R 1 and R 2 together with the nitrogen atom to which they are bound form a 4- to 7-membered cycle containing carbon atoms as ring members and optionally containing one oxygen atom as a ring member; R 3 is trifluoromethyl; R 4 is group A1

wherein X is C—R 12 and each R 12 is independently hydrogen, halogen or trihalomethyl, wherein at least two R 12 are not hydrogen; R 5b is halogen or methyl.

15. A compound according to claim 14 , wherein A 1 is C—R 5b ; A 2 , A 3 and A 4 are C—H; Y 1 —Y 2 —Y 3 is —C═N—O—, —C═N—S—, —C═N—

Assignees

• Syngenta Participations Ag

Inventors

• Rawal Girish
• Patre Rupesh
• Berthon Guillaume
• Cassayre Jerome Yves
• El Qacemi Myriem

Classifications

• C07D333/24

  Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals · CPC title

• C07D261/04

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

• A01N43/10

  with sulfur as the ring hetero atom · CPC title

• C07D333/18

  by sulfur atoms · CPC title

• A61P9/00

  Drugs for disorders of the cardiovascular system · CPC title