Pyrazoline derivatives as insecticidal compounds
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.
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.