Insecticidal aryl isoxazoline derivatives

1. A compound represented by formula (I):

wherein

A represents C or N;

R represents alkyl or haloalkyl;

X which may be identical or different, represents halogen, haloalkyl, nitro, alkyl, alkoxy, cyano, haloalkoxy, alkylsulfinyl, alkylsulfenyl, alkylsulfonyl, haloalkylsulfinyl, haloalkylsulfenyl, haloalkylsulfonyl, amino, acylamino, alkoxycarbonylamino, haloalkylcarbonylamino, haloalkoxycarbonylamino, alkylsulfonylamino, haloalkylsulfonylamino, hydroxyl or mercapto;

Y which may be identical or different, represents halogen, haloalkyl, nitro, alkyl, alkoxy, cyano, haloalkoxy, alkylsulfinyl, alkylsulfenyl, alkylsulfonyl, haloalkylsulfinyl, haloalkylsulfenyl, haloalkylsulfonyl, hydroxyl, mercapto, amino, acylamino, alkoxycarbonylamino, haloalkylcarbonylamino, haloalkoxycarbonylamino, alkylsulfonylamino or haloalkylsulfonylamino; or two adjacent Y, together with the carbon atoms to which they are attached to, form an optionally substituted cycle;

l represents 0, 1, 2, 3, 4 or 5;

m represents 0, 1, 2, 3 or 4;

n represents 1, 2 or 3;

R 1 and R 2 each independently represent hydrogen, alkyl, optionally substituted cycloalkyl, haloalkyl, cyano, alkoxycarbonyl, alkenyl or alkynyl, or alternatively R 1 and R 2 together represent C 2-5 alkylene;

R 3 represents hydrogen, alkyl, optionally substituted cycloalkyl, haloalkyl, cyano, alkenyl, alkynyl, alkylcarbonyl or CH 2 —R 5 , wherein R 5 represents optionally substituted phenyl or an optionally substituted heterocyclic group; and

R 4 represents hydrogen, formyl, cyano, alkylcarbonyl, alkylthiocarbonyl, haloalkylcarbonyl, haloalkylthiocarbonyl, alkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl, alkoxyaminocarbonyl, alkoxythiocarbonyl, alkoxyaminothiocarbonyl, alkoxycarbonyl, thioalkoxycarbonyl, thioalkoxythiocarbonyl,

alkylsulfonyl or haloalkylsulfonyl, wherein R 5 is as defined above.

2. A compound according to claim 1 , wherein

A represents C or N;

R represents C 1-6 alkyl or C 1-6 haloalkyl;

X which may be identical or different, represents halogen, C 1-6 haloalkyl, nitro, C 1-6 alkyl, C 1-6 alkoxy, cyano, C 1-6 haloalkoxy, C 1-6 alkylsulfinyl, C 1-6 alkylsulfenyl, C 1-6 alkylsulfonyl, C 1-6 haloalkylsulfinyl, C 1-6 haloalkylsulfenyl, C 1-6 haloalkylsulfonyl, amino, C 1-6 alkylcarbonyl, C 1-6 alkoxycarbonylamino, C 1-6 haloalkylcarbonylamino, C 1-6 haloalkoxycarbonylamino, C 1-6 alkylsulfonylamino, C 1-6 haloalkylsulfonylamino, hydroxyl or mercapto;

Y which may be identical or different, represents halogen, C 1-6 haloalkyl, nitro, C 1-6 alkyl, C 1-6 alkoxy, cyano, C 1-6 haloalkoxy, C 1-6 alkylsulfinyl, C 1-6 alkylsulfenyl, C 1-6 alkylsulfonyl, C 1-6 haloalkylsulfinyl, C 1-6 haloalkylsulfenyl, C 1-6 haloalkylsulfonyl, hydroxyl, mercapto, amino, C 1-4 alkylcarbonylamino, benzoylamino, C 1-6 alkoxycarbonylamino, C 1-6 haloalkylcarbonylamino, C 1-6 haloalkoxycarbonylamino, C 1-6 alkylsulfonylamino or C 1-6 haloalkylsulfonylamino; or two adjacent Y, together with the carbon atoms to which they are attached to, form an optionally substituted benzene;

l represents 0, 1, 2 or 3;

m represents 0, 1 or 2;

n represents 1;

R 1 and R 2 each independently represent hydrogen, C 1-6 alkyl, optionally substituted C 3-7 cycloalkyl, C 1-6 haloalkyl, cyano, C 1-6 alkoxycarbonyl, C 2-4 alkenyl or C 2-4 alkynyl, or alternatively R 1 and R 2 together represent C 2-5 alkylene;

R 3 represents hydrogen, C 1-6 alkyl, optionally substituted C 3-7 cycloalkyl, C 1-6 haloalkyl, cyano, C 2-4 alkenyl, C 2-4 alkynyl, C 1-6 alkylcarbonyl or CH 2 —R 5 , wherein R 5 represents optionally substituted phenyl or an optionally substituted heterocyclic group; and

R 4 represents formyl, cyano, C 1-6 alkylcarbonyl, C 1-6 alkylthiocarbonyl, C 1-6 haloalkylcarbonyl, C 1-6 haloalkylthiocarbonyl, C 1-6 alkylaminocarbonyl, C 1-6 alkylaminothiocarbonyl, C 2-8 (total number of carbons) dialkylaminocarbonyl, C 2-8 (total number of carbons) dialkylaminothiocarbonyl, C 1-6 alkoxyaminocarbonyl, C 1-6 alkoxythiocarbonyl, C 1-6 alkoxyaminothiocarbonyl, C 1-6 alkoxycarbonyl, thio-C 1-6 alkoxycarbonyl, thio-C 1-6 alkoxythiocarbonyl,

C 1-6 alkylsulfonyl or C 1-6 haloalkyl-sulfonyl, wherein R 5 is as defined above.

3. A composition for controlling insects, comprising the compound according to claim 1 or 2 and an extender a carrier, a surfactant, or combinations thereof.

4. Pharmaceutical composition comprising a compound according to claim 1 or 2 .

5. A method for controlling animal pests, comprising applying the compound according to claim 1 to animal pests, animal habitats or a combination thereof.

6. A method of preparing a pharmaceutical composition for controlling pests on animals, comprising mixing the compound according to claim 1 with an extender, a carrier, a surfactant, or combinations thereof.

7. A method of treating a seed, comprising applying the compound according to claim 1 to the seed.

8. A method of treating a transgenic plant, comprising applying the compound according to claim 1 to the transgenic plant.

9. The compound of claim 1 , wherein the compound is: