IP Library › Granted Patent US 11,001,577

Granted Patent B2

US 11,001,577 · App. 16/471,497 · Granted May 11, 2021

Pesticidally active azetidine sulfones amide isoxazoline derivatives

Inventors: Myriem El Qacemi (Stein, CH); Jérôme Yves Cassayre (Münchwilen, CH); Thomas Pitterna (Stein, CH); André Stoller (Stein, CH); Peter Renold (Stein, CH)

Assignee: SYNGENTA PARTICIPATIONS AG

C07D413/12 A01N43/80

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Quick Facts

Patent No.: US 11,001,577
App. No.: 16/471,497
Granted: May 11, 2021
Kind: B2

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Abstract

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, can be used as insecticides and can be prepared in a manner known per se.

Claims (309)

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 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 halogen, C 1 -C 8 alkoxy, amino, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 8 haloalkoxy, C 1 -C 8 alkylamino, C 1 -C 8 alkylamino wherein the alkyl group is substituted by R 6a , C 1 -C 8 alkenylamino, —NHC(O)NR a R b , C 1 -C 8 dialkylamino, C 1 -C 8 dialkylamino wherein one or both of the alkyl groups are independently substituted by R 6a , C 1 -C 8 dialkenylamino, C 1 -C 8 haloalkylamino, C 1 -C 8 dihaloalkylamino, C 3 -C 8 cycloalkyl, C 1 -C 8 alkyl substituted by R 6a , C 2 -C 6 alkenyl substituted by R 6b , C 2 -C 6 alkynyl substituted by R 6b , C 3 -C 8 cycloalkyl substituted by R 6b or —R c CO(O)R d , wherein R a R b , R c and R d are independently of each other C 1 -C 8 alkyl;

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 ;

each 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 2 —CH 2 —CH 2 — bridge, a —CH═CH—CH═CH— bridge or a —N═CH—CH═CH— bridge;

each R 6a is independently cyano, C 3 -C 8 cycloalkyl, C 2 -C 8 alkynyl, C 1 -C 8 alkoxy, C 1 -C 8 alkoxy-C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, C 1 -C 8 alkylcarbonyloxy, —C(O)NH 2 or ═NOR f , wherein R f is C 1 -C 8 alkyl;

each R 6b is independently halogen, cyano, 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 alkoxyC 1 -C 8 alkyl; and

each 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;

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 hydrogen, C 1 -C 8 alkyl, C 1 -C 8 alkylcarbonyl- or C 1 -C 8 alkoxycarbonyl.

3. A compound of formula (I) according to claim 1 , wherein

R 2 is halogen, C 1 -C 4 alkoxy, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylamino, C 1 -C 4 alkylamino wherein the alkyl group is substituted by R 6a , C 1 -C 4 alkenylamino, —NHC(O)NR a R b , C 1 -C 4 dialkylamino, C 1 -C 4 dialkylamino wherein one or both of the alkyl groups are independently substituted by R 6a , C 1 -C 4 dialkenylamino, C 1 -C 4 haloalkylamino, C 1 -C 4 dihaloalkylamino, C 3 -C 6 cycloalkyl, C 1 -C 4 alkyl substituted by R 6a , C 2 -C 4 alkenyl substituted by R 6b , C 2 -C 4 alkynyl substituted by R 6b , C 3 -C 6 cycloalkyl substituted by R 6b or —R c CO(O)R d , wherein R a , R b , R a and R d are, independently of each other, C 1 -C 8 alkyl.

4. A compound of formula (I) according to claim 1 , wherein

R 3 is C 1 -C 4 haloalkyl.

5. A compound of formula (I) according to claim 1 , wherein

R 4 is phenyl or phenyl substituted by one to three R 7 .

6. A compound of formula (I) according to claim 1 , wherein

each R 5 is independently halogen, cyano, nitro, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 3 -C 8 cycloalkyl or C 1 -C 8 haloalkyl.

7. A compound of formula (I) according to claim 1 , wherein

each R 6a is independently cyano;

each R 6b is independently halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or C 1 -C 4 alkoxyC 1 -C 4 alkyl.

8. A compound of formula (I) according to claim 1 , wherein

each R 7 is independently Cl, Br, F or CF 3 .

9. A compound of formula (I) according to claim 1 , wherein

A 1 is C—R 5 and A 2 , A 3 and A 4 are C—H.

10. A pesticidal composition, which comprises a 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.

11. A method for controlling pests, which comprises applying a composition according to claim 10 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 practiced on the human or animal body.

12. 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 10 .

13. A compound of formula (I) according to claim 1 , wherein A 1 is C—R 5 and A 2 , A 3 and A 4 are C—H.

14. A compound of formula (I) according to claim 13 , wherein R 5 is methyl.

15. A compound of formula (I) according to claim 14 , wherein R 4 is phenyl substituted by one to three R 7 , and each R 7 is independently Cl, Br, F or CF 3 .

16. A compound of formula (I) according to claim 15 , wherein R 1 is hydrogen.

17. A compound of formula (I) according to claim 15 , R 2 is halogen, C 1 -C 4 alkoxy, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylamino, C 1 -C 4 alkylamino wherein the alkyl group is substituted by R 6a , C 1 -C 4 alkenylamino, —NHC(O)NR a R b , C 1 -C 4 dialkylamino, C 1 -C 4 dialkylamino wherein one or both of the alkyl groups are independently substituted by R 6a , C 1 -C 4 dialkenylamino, C 1 -C 4 haloalkylamino, C 1 -C 4 dihaloalkylamino, C 3 -C 6 cycloalkyl, C 1 -C 4 alkyl substituted by R 6a , C 2 -C 4 alkenyl substituted by R 6b , C 2 -C 4 alkynyl substituted by R 6b , C 3 -C 6 cycloalkyl substituted by R 6b or —R c CO(O)R d , wherein R a , R b , R c and R d are, independently of each other, C 1 -C 8 alkyl.

18. A compound of formula (Int-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 1 -C 8 alkoxy, C 1 -C 8 alkoxy-C 1 -C 8 alkyl or C 1 -C 8 alkoxycarbonyl;

and R 6 is S(O) 2 R 2 ; and

X B is a halogen, or X B is cyano, formyl, CH═N—OH or acetyl;

R 2 is halogen, C 1 -C 8 alkoxy, amino, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 8 haloalkoxy, C 1 -C 8 alkylamino, C 1 -C 8 alkylamino wherein the alkyl group is substituted by R 6a , C 1 -C 8 alkenylamino, —NHC(O)NR a R b , C 1 -C 8 dialkylamino, C 1 -C 8 dialkylamino wherein one or both of the alkyl groups are independently substituted by R 6a , C 1 -C 8 dialkenylamino, C 1 -C 8 haloalkylamino, C 1 -C 8 dihaloalkylamino, C 3 -C 8 cycloalkyl, C 1 -C 8 alkyl substituted by R 6a , C 2 -C 6 alkenyl substituted by R 6b , C 2 -C 6 alkynyl substituted by R 6b , C 3 -C 8 cycloalkyl substituted by R 6b or —R c CO(O)R d , wherein R a , R b , R c and R d are independently of each other C 1 -C 8 alkyl;

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 ;

each 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; and

a salt or N-oxide thereof.

19. A compound of formula (Int-II)

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 1 -C 8 alkoxy, C 1 -C 8 alkoxy-C 1 -C 8 alkyl or C 1 -C 8 alkoxycarbonyl;

R 6 is S(O) 2 R 2 ;

X C is CH 2 -halogen, wherein halogen is bromo or chloro, CH═C(R 3 )R 4 or CH 2 C(OH)(R 3 )R 4 ;

R 2 is halogen, C 1 -C 8 alkoxy, amino, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 8 haloalkoxy, C 1 -C 8 alkylamino, C 1 -C 8 alkylamino wherein the alkyl group is substituted by R 6a , C 1 -C 8 alkenylamino, —NHC(O)NR a R b , C 1 -C 8 dialkylamino, C 1 -C 8 dialkylamino wherein one or both of the alkyl groups are independently substituted by R 6a , C 1 -C 8 dialkenylamino, C 1 -C 8 haloalkylamino, C 1 -C 8 dihaloalkylamino, C 3 -C 8 cycloalkyl, C 1 -C 8 alkyl substituted by R h a, C 2 -C 6 alkenyl substituted by R 6b , C 2 -C 6 alkynyl substituted by R 6b , C 3 -C 8 cycloalkyl substituted by R 6b or —R c CO(O)R d , wherein R a , R b , R c and R d are independently of each other C 1 -C 8 alkyl;

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 ;

each 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; and

a salt or N-oxide thereof.

20. A compound of formula (Int-III)

wherein

A 1 is C—R 5 ;

A 2 , A 3 and A 4 , independently are C—H;

R 1 is hydrogen;

R 3 is CF 3 ;

R 4 is phenyl substituted by one to three R 7 ;

R 5 is methyl;

R 6 is hydrogen;

each R 7 is independently halogen or C 1 haloalkyl; and

a salt or N-oxide thereof.

21. A compound of formula (A4),

wherein A 1 , A 2 , A 3 , A 4 , and R 2 are selected from the following combinations:

A 1

A 2

A 3

A 4

R 2

C—F

CH 3

cPr

C—F

CH 3

N(CH 3 ) 2

C—H

CH 3

N(CH 3 ) 2

C—H

CH 3

cPr

C—F

CH 3

C—H

CH 3

C—Cl

CH 3

C—F

CH 3

CH 2 CN

C—F

CH 3

NHCH 3

C—H

CF 3

CH 3

C—F

CH 3

1-methoxymethylcyclopropan-

1-yl

C—F

CH 3

NH 2

C—F

CH 3

N(CH 2 CF 3 ) 2

C—F

CH 3

NHCH 2 CF 3

C—H

CF 3

CH 3

NH 2

C—F

CH 3

N(CH 2 CHF 2 ) 2

C—Cl

CH 3

CHCH 2

C—H

CF 3

CH 3

OCH 2 CF 3

C—F

CH 3

N(CH 2 CN) 2

C—F

CH 3

NHC(O)N(CH 3 ) 2

C—F

CH 3

C(CH 2 ) 2 CN

C—F

CH 3

C(CH 2 ) 2 CH 3

C—F

CH 3

C(CH 3 ) 2 CN

C—Cl

CH 3

C(CH 2 ) 2 CN

C—Cl

CH 3

CH 2 OC(O)C(CH 3 ) 3

C—F

CH 3

cBu

C—F

CH 3

CH 2 OC(O)CH 2 CH 3

C—F

CH 3

CH 2 OC(O)C(CH 3 ) 3

C—F

CH 3

NHCH(CH 3 ) 2

C—F

CH 3

NHCH 2 C(O)NH 2

C—F

CH 3

NHCH 2 CH(CH 3 ) 2

C—F

CH 3

NHCH 2 CHC(CH 3 ) 2

C—F

CH 3

NHCH 2 CH 3

C—F

CH 3

NHCH 2 CH 2 CH 3

C—F

CH 3

NHCH 2 CH 2 OCH 2 CH 2 OCH 3

C—F

CH 3

N(CH 2 CH 2 OCH 3 ) 2

C—F

CH 3

N(CH 2 C(NOCH 3 )CH 3 ) 2

C—F

CH 3

NHCH 2 CH 2 CN

C—F

CH 3

NHCH 2 cBu

C—F

CH 3

N(allyl) 2

C—F

CH 3

NHCH 2 CH 2 OCH 2 CH 3

C—F

CH 3

N(CH 2 CH 2 OCH 2 CH 3 ) 2

C—F

CH 3

NHCH 2 cPr

C—F

CH 3

N(CH 2 cPr) 2

C—F

CH 3

N(CH 2 iPr) 2 .

Assignments (2)

MERGER AND CHANGE OF NAME Recorded Feb 28, 2025

From: SYNGENTA PARTICIPATIONS AG; SYNGENTA PARTICIPATIONS AG

To: SYNGENTA CROP PROTECTION AG

Reel/Frame 070362/0699 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 31, 2019

From: EL QACEMI, MYRIEM; CASSAYRE, JÈRÔME YVES; PITTERNA, THOMAS; RENOLD, PETER; STOLLER, ANDRÈ

To: SYNGENTA PARTICIPATIONS AG

Reel/Frame 049921/0304 →