Insecticidal triazinone derivatives

1. A compound of the formula I or I′:

wherein,

R 2 is hydrogen, formyl, C 1 -C 6 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 6 alkoxyC 1 -C 3 alkyl, C 1 -C 6 alkoxyC 1 -C 3 alkoxyC 1 -C 3 alkyl, C 2 -C 6 alkynyl, C 1 -C 4 cyanoalkyl, C 2 -C 6 alkenyl, phenylC 1 -C 4 alkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 4 alkoxycarbonylC 1 -C 4 alkyl, phenylC 1 -C 5 alkylcarbonyl, phenylC 1 -C 5 alkoxycarbonyl, heteroarylcarbonyl, phenylcarbonyl, C 1 -C 6 alkylsulfonyl, phenylsulfonyl, C 3 -C 6 cycloalkylcarbonyl, wherein a ring methylene group may optionally be replaced by O or S, C 3 -C 6 cycloalkoxycarbonyl, wherein a ring methylene group may optionally be replaced by O or S, C 3 -C 6 cycloalkylC 1 -C 4 alkylcarbonyl, wherein a ring or chain methylene group may optionally be replaced by O or S, C 1 -C 6 alkoxyC 1 -C 6 alkoxycarbonyl,

Y is N or C—R 3 , wherein R 3 is hydrogen, hydroxy, C 1 -C 4 alkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, wherein a ring methylene group may optionally be replaced by O or S, C 3 -C 6 cycloalkylC 1 -C 4 alkyl, wherein a ring or chain methylene group may optionally be replaced by O or S, halogen, cyano, or nitro, C 1 -C 3 haloalkylthio, C 1 -C 3 haloalkylsulfenyl, C 1 -C 3 haloalkylsulfonyl, or C 1 -C 3 haloalkoxy;

W is C—H or N;

n is 0 or 1;

Z is —N═CH— or —NR 4 —CH 2 — wherein R 4 is hydrogen, formyl, C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 2 -C 6 alkenyloxycarbonyl, C 2 -C 6 alkynyl, C 2 -C 6 alkenyl, or phenylC 1 -C 5 alkyloxycarbonyl;

R 1 is either Q 1 , Q 2 , or Q 3

Wherein,

X is O, S, or NR 5 wherein R 5 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl,

A 1 is hydrogen, C 1 -C 6 alkyl, C 1 -C 3 haloalkyl, C 2 -C 6 alkynyl, C 1 -C 4 cyanoalkyl, C 2 -C 6 alkenyl, phenylC 1 -C 4 alkyl, heteroarylC 1 -C 4 alkyl, phenyl, heteroaryl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, phenylC 1 -C 5 alkylcarbonyl, phenylcarbonyl, C 1 -C 6 alkylsulfonyl, phenylsulfonyl, C 3 -C 6 cycloalkyl, wherein a ring methylene group may optionally be replaced by O or S, C 3 -C 6 cycloalkylC 1 -C 4 alkyl, wherein a ring or chain methylene group may optionally be replaced by O or S, C 3 -C 6 cycloalkylcarbonyl, wherein a ring methylene group may optionally be replaced by O or S, or C 3 -C 6 cycloalkylC 1 -C 4 alkylcarbonyl, wherein a ring or chain methylene group may optionally be replaced by O or S;

A 2 is hydrogen, C 1 -C 6 alkyl, C 1 -C 3 haloalkyl, C 2 -C 6 alkynyl, C 1 -C 4 cyanoalkyl, C 2 -C 6 alkenyl, phenylC 1 -C 4 alkyl, heteroarylC 1 -C 4 alkyl, phenyl, heteroaryl, C 3 -C 6 cycloalkyl, wherein a ring methylene group may optionally be replaced by O or S, C 3 -C 6 cycloalkylC 1 -C 4 alkyl, wherein a ring or chain methylene group may optionally be replaced by O or S, C 1 -C 6 alkylamino, C 1 -C 6 dialkylamino, C 1 -C 6 alkyloxy, hydroxy, amino;

B 1 is CR 6 R 7 , or C(O), S(O) m , wherein m is 1 or 2

B 2 is CR 8 R 9 , O, NR 10 wherein R 10 is hydrogen, C 1 -C 6 alkyl, or C 1 -C 6 haloalkyl;

C 1 is CR 11 R 12 , C(O);

C 2 is CR 13 R 14 ;

C 3 is CR 15 R 16 , O, NR 17 ; wherein R 17 is hydrogen, C 1 -C 6 alkyl, or C 1 -C 6 haloalkyl,

wherein R 6 , R 7 , R 8 , R 9 , R 11 , R 12 , R 13 , R 14 R 15 , and R 16 are each independently of the other hydrogen, C 1 -C 6 alkyl, C 1 -C 3 haloalkyl, phenyl, heteroaryl, C 3 -C 6 cycloalkyl, wherein a ring methylene group may optionally be replaced by O or S, C 3 -C 6 cycloalkyl(C 1 -C 4 )alkyl, wherein a ring or chain methylene group may optionally be replaced by O or S, or

wherein R 6 , R 7 , R 8 , R 9 , R 11 , R 12 , R 13 , R 14 R 15 , and R 16 form a 3-6-membered carbocycle wherein a ring methylene group may optionally be replaced by O or S,

wherein the phenyl and the heteroaryl groups above may independently of each other optionally be substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, halogen, cyano, or by nitro,

or a tautomer thereof in each case in a free form or in salt form.

2. A compound according to claim 1 wherein R 2 is hydrogen, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, formyl, phenylC 1 -C 5 alkylcarbonyl, phenylC 1 -C 5 alkoxycarbonyl, phenylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, C 1 -C 6 alkoxyC 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl or formyl, wherein the phenyl groups above may independently of each other optionally be substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, halogen, cyano, or by nitro.

3. A compound according to claim 1 wherein Y is C—H, C—F, N, C—CF 3 , C—Cl, C—CH 3 , C-cyclo-Pr or C—CN.

4. A compound according to claim 1 wherein W is C—H.

5. A compound according to claim 1 wherein n is 0.

6. A compound according to claim 1 wherein Z is —N═CH— or —NH—CH 2 —.

7. A compound according to claim 1 wherein R 1 is Q 1 ,

X is O, N—CH 3 or N—H,

A 1 is hydrogen, C 1 -C 6 alkyl, C 1 -C 3 haloalkyl, C 2 -C 6 alkynyl, C 2 -C 6 alkenyl, phenylC 1 -C 4 alkyl, heteroarylC 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, wherein a ring methylene group may optionally be replaced by O or S, or C 3 -C 6 cycloalkylC 1 -C 4 alkyl, wherein a ring or chain methylene group may optionally be replaced by O or S, C 1 -C 6 alkyl, C 1 -C 3 haloalkyl, and

A 2 is hydrogen, C 1 -C 6 alkyl, C 1 -C 3 haloalkyl, phenyl, heteroaryl or C 3 -C 6 cycloalkyl, or C 1 -C 4 alkyl, wherein the phenyl and the heteroaryl groups above may independently of each other optionally be substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, halogen, cyano, or by nitro.

8. A compound according to claim 1 wherein R 1 is Q 2 ,

X is —O, N—CH 3 or N—H,

B 1 is CH 2 , CH(CH 3 ), CH(CF 3 ), C(CF 3 )(CH 3 ), C(CH 3 ) 2 , C(CF 3 ) 2 , C(CH 2 ) 2 , S(O) 2 , C(Aryl)(H) or C(Aryl)(CH 3 ), and

B 2 is O, NH, N(CH 3 ) or CH 2 .

9. A compound according to claim 1 wherein R 1 is Q 3 ,

X is O, N—CH 3 or N—H,

C 1 is CH 2 , C(O), CH(CH 3 ), C(CH 3 ) 2 or C(CH 2 ) 2 ,

C 2 is CH 2 , CH(CH 3 ), C(CH 3 ) 2 or C(CH 2 ) 2 ,

and

C 3 is CH 2 , NH, N(CH 3 ), or O.

10. A compound according to claim 1 wherein:

R 2 is H, C(O)CH 3 , C(O)Ot-Bu, C(O)OCH 2 Ph, C(O)OEt, C(O)O(CH 2 ) 2 OCH 3 , C(O)iso-Butyl, C(O)iso-Propyl, or C(O)cyclo-Pr,

Y is C—H, C—F, C—Cl, C—Br, C—CH 3 , C—CF 3 , C-cyclo-Pr, C—C≡N, C—CH═CH 2 , or N,

W is C—H or N,

n is 0 or 1,

Z is N═CH or NH—CH 2 ,

R 1 is Q 1 with X is O, N-Me or NH, A 1 is H, CH 3 , ethyl, CH 2 CF 3 , tert-Butyl, 3,5-Cl 2 C 6 H 3 , CH 2 -2,6-Cl 2 C 6 H 3 , A 2 is H, CH 3 , Ethyl, CF 3 , t-C 4 H 9 , 3,5-Cl 2 C 6 H 3 .

11. A compound according to claim 1 wherein:

R 2 is H, C(O)CH 3 , C(O)Ot-Bu, C(O)OCH 2 Ph, C(O)OEt, C(O)O(CH 2 ) 2 OCH 3 , C(O)iso-Butyl, C(O)iso-Propyl, or C(O)cyclo-Pr,

Y is C—H, C—F, C—Cl, C—Br, C—CH 3 , C—CF 3 , C-cyclo-Pr, C—C≡N, C—CH═CH 2 , or N,

W is C—H or N,

n is 0 or 1,

Z is N═CH or NH—CH 2 ,

R 1 is Q 2 with X is O, N-Me or NH, B 1 is CMe 2 , CHMe, C(CF 3 )Me, C(CF 3 ) 2 , CH(CF 3 ), CH(3,5-Cl 2 C 6 H 3 ), CH(2,6-Cl 2 C 6 H 3 ), C(CF 3 )(3,5-Cl 2 C 6 H 3 ), C(CH 2 ) 2 , B 2 is CH 2 , O or NH.

12. A compound according to claim 1 wherein:

R 2 is H, C(O)CH 3 , C(O)Ot-Bu, C(O)OCH 2 Ph, C(O)OEt, C(O)O(CH 2 ) 2 OCH 3 , C(O)iso-Butyl, C(O)iso-Propyl, or C(O)cyclo-Pr,

Y is C—H, C—F, C—Cl, C—Br, C—CH 3 , C—CF 3 , C-cyclo-Pr, C—C≡N, C—CH═CH 2 , or N,

W is C—H or N,

n is 0 or 1,

Z is N═CH or NH—CH 2 ,

R 1 is Q 3 with X is O, N-Me or NH, C 1 is CH 2 or C(O), C 2 is CH 2 , and C 3 is O, CH 2 or NH.

13. A pesticidal composition comprising a pesticidal effective amount of a compound of formula I or I′ according to claim 1 .

14. A pesticidal composition according to claim 13 , further comprising formulation adjuvants.

15. A pesticidal composition according to claim 13 , further comprising at least one additional insecticide, acaricide, nemacitide or molluscicide.

16. A pesticidal composition according to claim 13 , further comprising at least one additional fungicide, herbicide, or plant growth regulator.

17. A method of combating and controlling pest which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest a pesticidally effective amount of a compound of formula I or I′ according to claim 1 .

18. A method of combating and controlling pest which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest a pesticidal composition according to claim 13 .

19. A method of combating and controlling pest from the order Hemiptera which are resistant to a neonicotinoid insecticide, which method comprises applying a compound of the formula (I) or (I′) according to claim 1 in free form or in agrochemically acceptable salt form to said neonicotinoid resistant insects.