Pesticidal arylpyrrolidines
The invention is directed to arylpyrrolidines compounds which exhibit excellent insecticidal efficacy and which may be used as in the agrochemical field or in the vield of veterinary medicine. The compounds are represented by formula (I): wherein the respective substituents are defined in the specification.
1. An arylpyrrolidine compound having the formula
or salts thereof,
wherein
A 1 represents C—Y 2-4 or nitrogen;
X 1 , X 2-1 , X 2-2 , X 2-3 and X 2-4 each independently represents hydrogen, halogen, nitro, cyano, hydroxy, mercapto, amino, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, haloalkylsulfanyl, haloalkylsulfinyl, haloalkylsulfonyl, acylamino, alkoxycarbonylamino, haloalkoxycarbonylamino, alkoxyimino, haloalkoxyimino, alkylsulfonylamino, or pentafluorosulfur;
Y 2-1 , Y 2-3 , and Y 2-4 each independently represents hydrogen, halogen, nitro, cyano, hydroxy, mercapto, amino, alkyl, haloalkyl, cycloalkyl, cyclohaloalkyl, alkenyl, alkynyl, alkoxy, haloalkoxy, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, haloalkylsulfanyl, haloalkylsulfinyl, haloalkylsulfonyl, alkylsulfonyloxy, haloalkylsulfonyloxy, alkylaminosulfonyl, haloalkylaminosulfonyl, dialkylaminosulfonyl, di(haloalkyl)aminosulfonyl, alkylamino, dialkylamino, acylamino, alkoxycarbonylamino, haloalkoxycarbonylamino, alkylsulfonylamino, haloalkylsulfonylamino, trialkylsilyl, alkoxyimino, haloalkoxyimino, alkoxyiminoalkyl, haloalkoxyiminoalkyl, alkylsulfinylimino, alkylsulfinyliminoalkyl, alkylsulfinyliminoalkylcarbonyl, alkylsulfoxyimino, alkylsulfoxyiminoalkyl, alkoxycarbonyl, alkylcarbonyl, aminocarbonyl, alkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminocarbonyl, or dialkylaminothiocarbonyl;
R 3 and R 4 each independently represents hydrogen, cyano, alkyl, alkenyl, alkynyl, cycloalkyl or alkoxycarbonyl;
R 5-1 represents hydrogen, amino, hydroxy, cyano, alkyl, haloalkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, aminocarbonylalkyl, iminoalkyl, alkylcarbonyl, alkylcarbonylamino, alkylimino, aryl, aralkyl, a heterocycle, a heterocyclic ring substituted alkyl, R 7 —C(═O)—, or R 7 —C(═S)—;
R 6-1 represents C 3-6 cycloalkyl(C 1-4 )alkylcarbonyl, C 1-4 -alkoxy(C 1-4 )alkylcarbonyl, C 1-4 alkyl-S(C 1-4 )alkylcarbonyl, C 1-4 alkyl-SO(C 1-4 )alkylcarbonyl, C 1-4 alkyl-SO 2 (C 1-4 )alkylcarbonyl,
R 7 represents phenyl or a saturated or unsaturated heterocyclic ring.
2. The arylpyrrolidine compound of claim 1 , wherein
X 1 , X 2-1 , X 2-2 , X 2-3 and X 2 -4 each independently represents hydrogen, halogen or haloalkyl;
Y 2-1 , Y 2-3 , and Y 2-4 each independently represents hydrogen, halogen, alkyl, haloalkyl, alkoxy, cycloalkyl, haloalkoxy, alkylsulfonyl, or haloalkylsulfinyl;
R 3 , R 4 each independently represents hydrogen or alkyl;
R 5-1 represents hydrogen, alkyl, or haloalkyl; and
R 6-1 represents C 3-6 cycloalkyl(C 1-4 )alkylcarbonyl, C 1-4 alkoxy(C 1-4 )alkylcarbonyl, C 1-4 alkyl-S(C 1-4 )alkylcarbonyl, C 1-4 alkyl-SO(C 1-4 )alkylcarbonyl, C 1-4 alkyl-SO 2 (C 1-4 )alkylcarbonyl,
3. The arylpyrrolidine compound of claim 1 , wherein
X 1 , Y 2-1 , Y 2-2 , Y 2-3 and X 2-4 each independently represents hydrogen, halogen or C 1-4 -haloalkyl;
Y 2-1 , Y 2-3 , and Y 2-4 each independently represents hydrogen, halogen, C 1-4 -alkyl, C 1-4 -alkoxy, C 1-4 -haloalkoxy, C 3-6 -cycloalkyl, C 1-4 -haloalkyl, C 1-4 alkylsulfanyl, or C 1-4 -haloalkylsulfanyl;
R 3 or R 4 independently of each other represents hydrogen;
R 5-1 represents hydrogen, C 1-4 alkyl or C 1-4 -haloalkyl; and
R 6-1 is selected from the group consisting of
4. The arylpyrrolidine compound of claim 2 , wherein at least one of X 1 , X 2-1 , X 2-2 , X 2-3 and X 2-4 is hydrogen.
5. The arylpyrrolidine compound of claim 2 , wherein at least one of X 1 , X 2-2 , and X 2-4 is hydrogen.
6. The arylpyrrolidine compound of claim 2 , wherein X 1 and X 2-4 are hydrogen, and X 2-1 , X 2-2 , and X 2-3 each independently is selected from the group consisting of CF 3 , F, Cl, and Br.
7. An arylpyrrolidine compound having the formula
or salts thereof,
wherein
X 1 , X 2-1 , X 2-2 , X 2-3 and X 2-4 each independently represents hydrogen, halogen, nitro, cyano, hydroxy, mercapto, amino, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, haloalkylsulfanyl, haloalkylsulfinyl, haloalkylsulfonyl, acylamino, alkoxycarbonylamino, haloalkoxycarbonylamino, alkoxyimino, haloalkoxyimino, alkylsulfonylamino, or pentafluorosulfur;
Y 2-3 and Y 2-4 each independently represents hydrogen, halogen, nitro, cyano, hydroxy, mercapto, amino, alkyl, haloalkyl, cycloalkyl, cyclohaloalkyl, alkenyl, alkynyl, alkoxy, haloalkoxy, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, haloalkylsulfanyl, haloalkylsulfinyl, haloalkylsulfonyl, alkylsulfonyloxy, haloalkylsulfonyloxy, alkylaminosulfonyl, haloalkylaminosulfonyl, dialkylaminosulfonyl, di(haloalkyl)aminosulfonyl, alkylamino, dialkylamino, acylamino, alkoxycarbonylamino, haloalkoxycarbonylamino, alkylsulfonylamino, haloalkylsulfonylamino, trialkylsilyl, alkoxyimino, haloalkoxyimino, alkoxyiminoalkyl, haloalkoxyiminoalkyl, alkylsulfinylimino, alkylsulfinyliminoalkyl, alkylsulfinyliminoalkylcarbonyl, alkylsulfoxyimino, alkylsulfoxyiminoalkyl, alkoxycarbonyl, alkylcarbonyl, aminocarbonyl, alkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminocarbonyl, or dialkylaminothiocarbonyl;
R 3 and R 4 each independently represents hydrogen, cyano, alkyl, alkenyl, alkynyl, cycloalkyl or alkoxycarbonyl;
R 5-1 represents hydrogen, amino, hydroxy, cyano, alkyl, haloalkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, aminocarbonylalkyl, iminoalkyl, alkylcarbonyl, alkylcarbonylamino, alkylimino, aryl, aralkyl, a heterocycle, a heterocyclic ring substituted alkyl, R 7 —C(═O)—, or R 7 —C(═S)—;
R 6-1 represents C 3-6 cycloalkyl(C 1-4 )alkylcarbonyl, C 1-4 alkoxy(C 1-4 )alkylcarbonyl, C 1-4 alkyl-S(C 1-4 )alkylcarbonyl, C 1-4 alkyl-SO(C 1-4 alkylcarbonyl, C 1-4 alkyl-SO 2 (C 1-4 )alkylcarbonyl,
R 7 represents phenyl or a saturated or unsaturated heterocyclic ring.
8. The arylpyrrolidine compound of claim 7 , wherein
X 1 , X 2-1 , X 2-2 , X 2-3 and X 2-4 each independently represents hydrogen, halogen or haloalkyl;
Y 2-3 and Y 2-4 each independently represents hydrogen, halogen, alkyl, haloalkyl, alkoxy, cycloalkyl, haloalkoxy, alkylsulfonyl, or haloalkylsulfinyl;
R 3 and R 4 each independently represents hydrogen or alkyl;
R 5-1 represents hydrogen, alkyl, or haloalkyl; and
R 6-1 represents C 3-6 cycloalkyl(C 1-4 )alkylcarbonyl, C 1-4 alkoxy(C 1-4 )alkylcarbonyl, C 1-4 alkyl-S(C 1-4 )alkylcarbonyl, C 1-4 alkyl-SO(C 1-4 )alkylcarbonyl, C 1-4 alkyl-SO 2 (C 1-4 )alkylcarbonyl,
9. The arylpyrrolidine compound of claim 7 , wherein
X 1 , X 2-1 , X 2-2 , X 2-3 and X 2-4 each independently represents hydrogen, halogen or C 1-4 -haloalkyl;
Y 2-3 and Y 2-4 each independently represents hydrogen, halogen, C 1-4 -alkyl, C 1-4 -alkoxy, C 1-4 -haloalkoxy, C 3-6 -cycloalkyl, C 1-4 -haloalkyl, C 1-4 -alkylsulfanyl, or C 1-4 -haloalkylsulfanyl;
R 3 and R 4 independently of each other represents hydrogen;
R 5-1 represents hydrogen, C 1-4 alkyl or C 1-4 haloalkyl; and
R 6-1 is selected from the group consisting of
10. The arylpyrrolidine compound of claim 7 , wherein at least one of X 1 , X 2-1 , X 2-2 , X 2-3 and A 2-4 is hydrogen.
11. The arylpyrrolidine compound of claim 7 , wherein at least one of X 1 , X 2-2 , and X 2-4 is hydrogen.
12. The arylpyrrolidine compound of claim 7 , wherein X 1 and X 2-4 are hydrogen, and X 2-1 , X 2-2 , and X 2-3 each independently is selected from the group consisting of CF 3 , F, Cl, and Br.
13. A composition comprising one or more compounds selected from the compounds according to claim 1 and one or more diluents, emulsifiers, or a combination thereof.
14. A composition comprising one or more compounds selected from the compounds according to claim 3 and one or more diluents, emulsifiers, or a combination thereof.
15. A composition comprising one or more compounds selected from the compounds according to claim 7 and one or more diluents, emulsifiers, or a combination thereof.
16. A composition comprising one or more compounds selected from the compounds according to claim 9 and one or more diluents, emulsifiers, or a combination thereof.
17. A method for controlling plant damaging animal pests comprising applying the composition according to claim 13 or 14 to said pests, their habitat, or a combination thereof.
18. The method of claim 17 , wherein the composition according to claim 14 is applied to said pests, their habitat, or a combination thereof.
19. A method for controlling parasites in or on an animal comprising administering the composition according to claim 15 or 16 to said animal.
20. The method of claim 19 , wherein the composition according to claim 16 is applied to said animal.
21. A method for treating seeds of conventional or transgenic plants comprising administering the composition according to claim 13 or 14 to said seeds.
22. The method of claim 21 , wherein the composition according to claim 14 is applied to said seeds.
23. The arylpyrrolidine compound of claim 1 , wherein the compound is
24. The arylpyrrolidine compound of claim 1 , wherein the compound is
25. The arylpyrrolidine compound of claim 1 , wherein the compound is
26. The arylpyrrolidine compound of claim 1 , wherein the compound is
27. A composition comprising any of the compounds according to any of claims 23 - 26 and one or more diluents, emulsifiers, or a combination thereof.