Pyrazoline derivatives as insecticidal compounds

Patent metadata

Field	Value
Publication number	US-10287281-B2
Application number	US-201715628804-A
Country	US
Kind code	B2
Filing date	Jun 21, 2017
Priority date	Jan 23, 2013
Publication date	May 14, 2019
Grant date	May 14, 2019

Abstract

The present invention relates to compounds of formula I

wherein
P is selected from P1 and P2, or P and R 5 together are P3

or P is a heterocycle H, selected from H1 to H9

wherein Y 1 , Y 2 , and Y 3 are independently of each other C—H, C—R 5 , or nitrogen; and G 1 , G 2 , G 3 , Z, R 1 , R 2 , R 3 , R 4 , R 5 , R 6a , R 6b , R 7 , R 8 , R 9 , R 10 , R 11 , p, n and k are as defined in the claims. The invention also relates to methods of controlling insects, acarines, nematodes or molluscs which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula I.

First claim

The invention claimed is:

1. A compound of formula Int-I

wherein
Y 1 , Y 2 , and Y 3 are independently of each other C—H, C—R 5 , or nitrogen;
G 1 is oxygen or sulfur;
R 3 is C 1 -C 8 haloalkyl;
R 4 is aryl or aryl substituted by one to five R 15 , or heteroaryl or heteroaryl substituted by one to five R 15 ;
each R 5 is independently hydrogen, halogen, cyano, nitro, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 1 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, C 3 -C 10 cycloalkyl, C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, 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, or two R 5 on adjacent carbon atoms together form a —CH═CH—CH═CH— bridge or a —N═CH—CH═CH— bridge;
R 6a and R 6b are each independently hydrogen, halogen, cyano, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, or C 3 -C 8 cycloalkyl, or R 6a and R 6b together with the carbon atom to which they are attached may form a 3 to 6-membered carbocyclic ring;
each R 15 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, or C 1 -C 8 alkoxycarbonyl; and
R is hydroxy, C 1 -C 15 alkoxy or halogen; or a salt or N-oxide thereof; or
a compound of formula Int-II

wherein
Y 1 , Y 2 , and Y 3 are independently of each other C—H, C—R 5 , or nitrogen;
R 3 is C 1 -C 8 haloalkyl;
R 4 is aryl or aryl substituted by one to five R 15 , or heteroaryl or heteroaryl substituted by one to five R 15 ;
each R 5 is independently hydrogen, halogen, cyano, nitro, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 1 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, C 3 -C 10 cycloalkyl, C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, 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, or two R 5 on adjacent carbon atoms together form a —CH═CH—CH═CH— bridge or a —N═CH—CH═CH— bridge;
R 6a and R 6b are each independently hydrogen, halogen, cyano, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, or C 3 -C 8 cycloalkyl, or R 6a and R 6b together with the carbon atom to which they are attached may form a 3 to 6-membered carbocyclic ring;
each R 15 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, or C 1 -C 8 alkoxycarbonyl; and
R a and R b are independently selected from hydrogen, C 1 -C 8 carbonyl, C 1 -C 8 alkoxycarbonyl, or R a and R b together are —C(═O)—(CH 2 ) r —C(═O)—wherein r is 1 to 4, —C(C 1 -C 3 alkyl)═C—C═(C 1 -C 3 alkyl)C—, or group D

or a salt or N-oxide thereof; or
a compound of formula Int-III

wherein
Y 1 , Y 2 , and Y 3 are independently of each other C—H, C—R 5 , or nitrogen;
R 3 is C 1 -C 8 haloalkyl;
R 4 is aryl or aryl substituted by one to five R 15 , or heteroaryl or heteroaryl substituted by one to five R 15 ;
each R 11 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, or C 1 -C 8 alkoxycarbonyl;
each R 15 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, or C 1 -C 8 alkoxycarbonyl;
n is 1 or 2; and
R a and R b , are as defined for the compounds of formula Int-II, or a salt or N-oxide thereof.

2. The compound of claim 1 , wherein the compound has the formula Int-I.

3. The compound of claim 2 , wherein R 3 is trifluoromethyl.

4. The compound of claim 2 , wherein R 4 is aryl substituted by one to three R 15 , wherein R 15 is halogen or C 1 -C 8 haloalkyl.

5. The compound of claim 2 , wherein R 5 is halogen, cyano, C 1 -C 8 alkyl, or C 1 -C 8 haloalkyl.

6. The compound of claim 2 , wherein Y 1 , Y 2 , and Y 3 are C—H.

7. The compound of claim 1 , wherein the compound has the formula Int-II.

8. The compound of claim 7 , wherein R 3 is trifluoromethyl.

9. The compound of claim 7 , wherein R 4 is aryl substituted by one to three R 15 , wherein R 15 is halogen or C 1 -C 8 haloalkyl.

10. The compound of claim 7 , wherein R 5 is halogen, cyano, C 1 -C 8 alkyl, or C 1 -C 8 haloalkyl.

11. The compound of claim 7 , wherein Y 1 , Y 2 , and Y 3 are C—H.

12. The compound of claim 1 , wherein the compound has the formula Int-III.

13. The compound of claim 12 , wherein R 3 is trifluoromethyl.

14. The compound of claim 12 , wherein R 4 is aryl substituted by one to three R 15 , wherein R 15 is halogen or C 1 -C 8 haloalkyl.

15. The compound of claim 12 , wherein R 5 is halogen, cyano, C 1 -C 8 alkyl, or C 1 -C 8 haloalkyl.

16. The compound of claim 12 , wherein Y 1 , Y 2 , and Y 3 are C—H.

Assignees

• Syngenta Participations Ag

Inventors

• Lu Long
• Cassayre Jerome Yves
• Berthon Guillaume
• El Qacemi Myriem
• Wu Yaming

Classifications

• C07D413/12 Primary

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

• C07D231/06

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

• A01N53/00

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

• A01N43/90

  having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system · CPC title

• A01N43/60

  1,4-Diazines; Hydrogenated 1,4-diazines · CPC title