Stable formulation of pesticidal pyridazinpyrazolamides

1. An agrochemical composition comprising

a) propylene carbonate

b) up to 10 wt % of water based on the total weight of the composition;

c) compound (I)

or a salt, a tautomer, or an enantiomer thereof; and

d) cyclohexanone;

wherein the variables have the meaning

R 1 H, C 1 -C 2 -alkyl, or C 1 -C 2 -alkoxy-C 1 -C 2 -alkyl;

R 2 H, halogen, CN, or NO 2 ;

C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, or C 2 -C 10 -alkynyl, which are unsubstituted, halogenated, or substituted with R x ;

OR a , SR a , C(Y)R b , C(Y)OR c , S(O)R d , S(O) 2 R d , NR e R f , C(Y)NR g R h ; heterocyclyl, hetaryl, C 3 -C 10 -cycloalkyl, C 3 -C 10 -cycloalkenyl, or phenyl, which are unsubstituted, or substituted with R y , or R x ;

R 3 H, halogen, CN, NO 2 ;

C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, or C 2 -C 10 -alkynyl, which are unsubstituted, halogenated, or substituted with R x ;

OR a , SR a , C(Y)R b , C(Y)OR c , S(O)R d , S(O) 2 R d , NR e R f , C(Y)NR g R h ; heterocyclyl, hetaryl, C 3 -C 10 -cycloalkyl, C 3 -C 10 -cycloalkenyl or phenyl, which are unsubstituted, or substituted with R y , or R x ;

R N H, CN, NO 2 ;

C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, or C 2 -C 10 -alkynyl, which are unsubstituted, halogenated, or substituted with R x ;

OR a , SR a , C(Y)R b , C(Y)OR c , S(O)R d , S(O) 2 R d , NR e R f , C(Y)NR g R h , S(O) m NR e R f , C(Y)NR i NR e R f , C 1 -C 5 -alkylen-OR a , C 1 -C 5 -alkylen-CN, C 1 -C 5 -alkylen-C(Y)R b , C 1 -C 5 -alkylen-C(Y)OR c , C 1 -C 5 -alkylen-NR e R f , C 1 -C 5 -alkylen-C(Y)NR g R h , C 1 -C 5 -alkylen-S(O) m R d , C 1 -C 5 -alkylen-S(O) m NR e R f , C 1 -C 5 -alkylen-NR i NR e R f ; heterocyclyl, hetaryl, C 3 -C 10 -cycloalkyl, C 3 -C 10 -cycloalkenyl, heterocyclyl-C 1 -C 5 -alkyl, hetaryl-C 1 -C 5 -alkyl, C 3 -C 10 -cycloalkyl-C 1 -C 5 -alkyl, C 3 -C 10 -cycloalkenyl-C 1 -C 5 -alkyl, phenyl-C 1 -C 5 -alkyl, or phenyl, in which groups the rings are unsubstituted, or substituted with R y ;

R a , R b , R c independently H, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkylmethyl, C 3 -C 6 -halocycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl; or heterocyclyl, heterocyclyl-C 1 -C 4 -alkyl, phenyl, hetaryl, phenyl-C 1 -C 4 -alkyl, hetaryl-C 1 -C 4 -alkyl, in which groups the ring is unsubstituted, or substituted with halogen, CN, NO 2 , C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -haloalkoxy;

R d C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cyclo-alkylmethyl, C 3 -C 6 -halocycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl; or heterocyclyl, heterocyclyl-C 1 -C 4 -alkyl, phenyl, hetaryl, phenyl-C 1 -C 4 -alkyl, and hetaryl-C 1 -C 4 -alkyl, in which groups the ring is unsubstituted, or substituted with halogen, CN, NO 2 , C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -haloalkoxy;

R e , R f independently H, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkylmethyl, C 3 -C 6 -halocycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkyl-carbonyl, C 1 -C 4 -haloalkylcarbonyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylsulfonyl;

heterocyclyl, heterocyclyl-C 1 -C 4 -alkyl, heterocyclylcarbonyl, heterocyclylsulfonyl, phenyl, phenyl carbonyl, phenylsulfonyl, hetaryl, hetarylcarbonyl, hetarylsulfonyl, phenyl-C 1 -C 4 -alkyl, and hetaryl-C 1 -C 4 -alkyl, in which groups the ring is unsubstituted, or substituted with halogen, CN, NO 2 , C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, and C 1 -C 4 -haloalkoxy; or

R e and R f are together with the nitrogen atom to which they are bound form a 5-or 6-membered, saturated, or unsaturated heterocycle, in which heterocycle none, or one ring member atom is replaced by O, S or N, and wherein the heterocycle is unsubstituted or substituted with halogen, CN, NO 2 , C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -haloalkoxy;

R g , R h independently H, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl; heterocyclyl, heterocyclyl-C 1 -C 4 -alkyl, phenyl, hetaryl, phenyl-C 1 -C 4 -alkyl, and hetaryl-C 1 -C 4 -alkyl, in which groups the ring is unsubstituted, or substituted with halogen, CN, NO 2 , C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -haloalkoxy;

R i H, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkylmethyl, C 3 -C 6 -halocycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl; or phenyl, phenyl-C 1 -C 4 -alkyl, in which groups the phenyl rings is unsubstituted, or substituted with halogen, CN, NO 2 , C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -haloalkoxy;

R x CN, NO 2 , C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, S(O) m R d , S(O) m NR e R f , C 1 -C 10 alkylcarbonyl, C 1 -C 4 -haloalkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -haloalkoxycarbonyl; or C 3 -C 6 -cycloalkyl, 5- to 7-membered heterocyclyl, 5- or 6-membered hetaryl, phenyl, C 3 -C 6 -cycloalkoxy, 3- to 6-membered heterocyclyloxy, phenoxy, which are unsubstituted, or substituted with R y ;

R y halogen, CN, NO 2 , C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, S(O) m R d , S(O) m NR e R f , C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -haloalkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -haloalkoxycarbonyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, or C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl;

Y O or S; and

m is 0, 1 or 2.

2. The agrochemical composition of claim 1 comprising

A) 1 to 25 wt % of propylene carbonate;

B) up to 5 wt % of water; and

C) 1 to 95 wt % of compounds I wherein the concentrations are based on the total weight of the composition.

3. The agrochemical composition of claim 1 comprising

A) 5 to 20 wt % of propylene carbonate;

B) up to 2 wt % of water; and

C) 1 to 90 wt % of compounds I wherein the concentrations are based on the total weight of the composition.

4. The agrochemical composition of claim 1 , wherein R 1 is CH 2 CH 3 , R 2 is CH 3 , R 3 is H, R N is CHR 4 R 5 ; and wherein

a) R 4 is CH 3 , R 5 is CH 3 ;

b) R 4 is CF 3 , R 5 is CH 3 ;

c) R 4 is CH(CH3) 2 , R 5 is CH 3 ;

d) R 4 is CHFCH 3 , R 5 is CH 3 ;

e) R 4 is 1-CN-cC 3 H 4 , R 5 is CH 3 ;

f) R 4 is 1-C(O)NH 2 -cC 3 H 4 , R 5 is CH 3 ; or

g) R 4 and R 5 together are CH 2 CH 2 CF 2 CH 2 CH 2 .

5. The agrochemical composition of claim 1 , wherein R 1 is CH 2 CH 3 , R 2 is CH 3 , R 3 is H, and R N is CH(CH 3 )CH(CH 3 ) 2 .

6. The agrochemical composition of claim 1 , wherein the pH of a 1% dilution of the composition in deionized water is in a range from 2 to 6.

7. The agrochemical composition of claim 1 , wherein the composition comprises an acid.

8. The agrochemical composition of claim 1 , wherein the concentration of cyclohexanone is from 0.1 to 30 wt % based on the total weight of the composition.

9. The agrochemical composition of claim 8 , further comprising an acid; wherein the concentration of propylene carbonate is from 0.1 to 50 wt % based on the total weight of the composition.

10. A process for the preparation of the agrochemical composition of claim 1 , comprising mixing the propylene carbonate, the cyclohexanone, the compound (I), and, when present, the water.

11. A method for controlling pests, which method comprises the application of the agrochemical composition of claim 1 , or a dilution thereof, to plants, plant propagation material, or the locus of growth of the plants; the pests or their food supply, habitat or breeding grounds.

12. The method of claim 11 , wherein the composition comprises

A) 5 to 20 wt % of propylene carbonate;

B) up to 2 wt % of water; and

C) 1 to 90 wt % of compounds I wherein the concentrations are based on the total weight of the composition.

13. The method of claim 11 , wherein R 1 is CH 2 CH 3 , R 2 is CH 3 , R 3 is H, R N is CHR 4 R 5 ; and wherein

a) R 4 is CHs, R 5 is CH 3 ;

b) R 4 is CF 3 , R 5 is CH 3 ;

c) R 4 is CH(CH 3 ) 2 , R 5 is CH 3 ;

d) R 4 is CHFCH 3 , R 5 is CH 3 ;

e) R 4 is 1-CN-cC 3 H 4 , R 5 is CH 3 ;

f) R 4 is 1-C(O)NH 2 -cC 3 H 4 , R 5 is CH 3 ; or

g) R 4 and R 5 together are CH 2 CH 2 CF 2 CH 2 CH 2 .

14. The method of claim 11 , wherein R 1 is CH 2 CH 3 , R 2 is CH 3 , R3 is H, and R N is CH(CH 3 )CH(CH 3 ) 2 .

15. The method of claim 11 , wherein the pH of a 1% dilution of the composition in deionized water is in a range from 2 to 6.

16. The method of claim 11 , wherein the composition comprises an acid.

17. The method of claim 11 , wherein the concentration of cyclohexanone is from 0.1 to 30 wt % based on the total weight of the composition.

18. The method of claim 11 , wherein the composition comprises

A) 1 to 25 wt % of propylene carbonate;

B) up to 5 wt % of water; and

C) 1 to 95 wt % of compounds I wherein the concentrations are based on the total weight of the composition.

19. An aqueous tank-mix composition comprising the agrochemical composition of claim 1 in a concentration of 0.01 wt % to 10 wt % based on the total weight of the aqueous tank-mix composition.