Pyrazoline derivatives as insecticidal compounds

Patent metadata

Field	Value
Publication number	US-9776994-B2
Application number	US-201414762319-A
Country	US
Kind code	B2
Filing date	Jan 23, 2014
Priority date	Jan 23, 2013
Publication date	Oct 3, 2017
Grant date	Oct 3, 2017

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 I

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

Y 1 , Y 2 , and Y 3 are independently of each other C—H, or C—R 5 ;
G 1 is oxygen or sulfur;
G 2 is oxygen or sulfur;
G 3 is oxygen or sulfur;
R 1 is hydrogen, C 1 -C 8 alkyl, C 1 -C 8 alkoxy, C 1 -C 6 alkylcarbonyl, or C 1 -C 8 alkoxycarbonyl;
R 2 is C 1 -C 8 alkyl or C 1 -C 8 alkyl substituted by one to five R 12 , C 3 -C 10 cycloalkyl or C 3 -C 10 cycloalkyl substituted by one to five R 13 , C 3 -C 10 cycloalkyl-C 1 -C 4 alkylene or C 3 -C 10 cycloalkyl-C 1 -C 4 alkylene substituted by one to five R 13 , aryl-C 1 -C 4 alkylene- or aryl-C 1 -C 4 alkylene-substituted by one to five R 14 , heterocyclyl-C 1 -C 4 alkylene- or heterocyclyl-C 1 -C 4 alkylene-substituted by one to five R 14 , aryl or aryl substituted by one to five R 14 , heterocyclyl or heterocyclyl substituted by one to five R 14 , C 1 -C 8 alkylaminocarbonyl-C 1 -C 4 alkylene, C 1 -C 8 haloalkylaminocarbonyl-C 1 -C 4 alkylene, C 3 -C 8 cycloalkyl-aminocarbonyl-C 1 -C 4 alkylene, aryl-CH 2 -aminocarbonyl-C 1 -C 4 alkylene or aryl-CH 2 -aminocarbonyl-C 1 -C 4 alkylene wherein the aryl is substituted by one to five R 14 , C 1 -C 8 alkylaminocarbonyl, C 1 -C 8 haloalkylaminocarbonyl, C 3 -C 6 cycloalkylaminocarbonyl, C 1 -C 6 alkyl-O—N═CH—, or C 1 -C 6 haloalkyl-O—N═CH—;
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;
R 7 is hydrogen, C 1 -C 8 alkyl, C 1 -C 8 alkoxy, C 1 -C 8 alkylcarbonyl, or C 1 -C 8 alkoxycarbonyl;
R 8 is C 1 -C 8 alkyl or C 1 -C 8 alkyl substituted by one to five R 12 , C 3 -C 10 cycloalkyl or C 3 -C 10 cycloalkyl substituted by one to five R 13 , C 3 -C 10 cycloalkyl-C 1 -C 4 alkylene or C 3 -C 10 cycloalkyl-C 1 -C 4 alkylene substituted by one to five R 13 , aryl-C 1 -C 4 alkylene- or aryl-C 1 -C 4 alkylene-substituted by one to five R 14 , heterocyclyl-C 1 -C 4 alkylene- or heterocyclyl-C 1 -C 4 alkylene-substituted by one to five R 14 , aryl or aryl substituted by one to five R 14 , or heterocyclyl or heterocyclyl substituted by one to five R 14 , each R 9 is independently hydrogen, C 1 -C 8 alkyl, C 1 -C 8 alkoxy, C 1 -C 8 alkylcarbonyl, or C 1 -C 8 alkoxycarbonyl;
R 10 is C 1 -C 8 alkyl or C 1 -C 8 alkyl substituted by one to five R 12 , C 3 -C 10 cycloalkyl or C 3 -C 10 cycloalkyl substituted by one to five R 13 , C 3 -C 10 cycloalkyl-C 1 -C 4 alkylene or C 3 -C 10 cycloalkyl-C 1 -C 4 alkylene substituted by one to five R 13 , aryl-C 1 -C 4 alkylene- or aryl-C 1 -C 4 alkylene-substituted by one to five R 14 , heterocyclyl-C 1 -C 4 alkylene- or heterocyclyl-C 1 -C 4 alkylene-substituted by one to five R 14 , aryl or aryl substituted by one to five R 14 , heterocyclyl or heterocyclyl substituted by one to five R 14 ;
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 12 is independently halogen, cyano, nitro, hydroxy, amino, C 1 -C 8 alkylamino, (C 1 -C 8 alkyl) 2 amino, C 1 -C 8 alkylcarbonylamino, C 1 -C 8 haloalkylcarbonylamino, C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, aryloxy or aryloxy substituted by one to five R 16 , aryloxy-C 1 -C 4 alkylene or aryloxy-C 1 -C 4 alkylene wherein the aryl moiety is substituted by one to five R 16 , 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, C 1 -C 8 haloalkylsulfonyl, aryl-C 1 -C 4 alkylthio or aryl-C 1 -C 4 alkylthio wherein the aryl moiety is substituted by one to five R 16 ;
each R 13 is independently halogen, cyano, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, or C 1 -C 8 alkoxy, C 1 -C 8 alkoxycarbonyl, or two R 13 are together R 19 —O—N═;
each R 14 is independently halogen, cyano, nitro, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 1 -C 8 cyanoalkyl, 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, C 3 -C 10 cycloalkyl-C 1 -C 4 alkylene, 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 alkylaminosulfonyl, (C 1 -C 8 alkyl) 2 aminosulfonyl, C 1 -C 8 alkylcarbonyl, C 1 -C 8 haloalkylcarbonyl, C 1 -C 8 alkoxycarbonyl, C 8 haloalkoxycarbonyl, aryl or aryl substituted by one to five R 16 , heterocyclyl or heterocyclyl substituted by one to five R 16 , aryl-C 1 -C 4 alkylene or aryl-C 1 -C 4 alkylene wherein the aryl moiety is substituted by one to five R 16 , heterocyclyl-C 1 -C 4 alkylene or heterocyclyl-C 1 -C 4 alkylene wherein the heterocyclyl moiety is substituted by one to five R 16 , aryloxy or aryloxy substituted by one to five R 16 , or aryloxy-C 1 -C 4 alkylene or aryloxy-C 1 -C 4 alkylene wherein the aryl moiety is substituted by one to five R 16 or two R 14 are together ═O;
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;
each R 16 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;
each R 19 is hydrogen, C 1 -C 8 alkyl or C 1 -C 8 haloalkyl;
each Z is independently halogen, cyano, C 1 -C 8 alkyl or C 1 -C 8 alkyl substituted by one to five R 12 , nitro, hydroxyl, 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, or C 1 -C 8 haloalkylsulfonyl;
k is 0, 1, or 2;
n is 1 or 2;
p is 0, 1, 2, 3, 4, or 5;
or a salt or N-oxide thereof.

2. A compound according to claim 1 , wherein P is P1.

3. A compound according to claim 1 , wherein P is P2.

4. A compound according to claim 1 , wherein P and R 5 together are P3.

5. A compound according to claim 1 , wherein Y 1 is C—H or nitrogen, Y 2 and Y 3 are independently C—H or nitrogen; wherein no more th

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