Acylacetonitriles, process for preparation thereof and miticides containing the same
The acylacetonitrile compound of the invention is represented by the formula (1): wherein R 1 represents —C(O)ZR 2 ; R 2 represents C 1-6 alkyl, C 1-4 haloalkyl or the like; Z represents oxygen or sulfur; X and Y independently represent halogen, C 1-6 alkyl or C 1-4 haloalkyl; and m and n are independently an integer of 1 to 3. The acylacetonitrile compound of the invention exhibits excellent miticidal and ovicidal activities for mites over a long period. Therefore, the acylacetonitrile compound of the invention is useful as a miticide.
1. An acylacetonitrile compound represented by the formula (1):
wherein R 1 represents —C(O)ZR 2 ; R 2 represents C 1-6 alkyl, C 1-4 haloalkyl, C 2-4 alkenyl, C 2-4 alkynyl, C 1-6 alkoxy-C 1-4 alkyl, C 1-4 alkylthio-C 1-4 alkyl or benzyl; Z represents oxygen or sulfur; X and Y independently represent halogen, C 1-6 alkyl or C 1-4 haloalkyl; m and n are independently an integer of 1 to 3; and m X's and n Y's may be the same or different, respectively.
2. An acylacetonitrile compound according to claim 1 , wherein Z in the formula (1) represents oxygen.
3. An acylacetonitrile compound according to claim 1 , wherein X in the formula (1) represents halogen or C 1-6 alkyl.
4. An acylacetonitrile compound according to claim 1 , wherein Y in the formula (1) represents at least one species selected from halogen and C 1-4 haloalkyl.
5. An acylacetonitrile compound according to claim 1 , wherein Z represents oxygen, X represents C 1-6 alkyl, and Y represents C 1-4 haloalkyl in the formula (1).
6. A process for preparing an acylacetonitrile compound represented by the formula (1):
wherein R 1 represents —C(O)ZR 2 ; R 2 represents C 1-6 alkyl, C 1-4 haloalkyl, C 2-4 alkenyl, C 2-4 alkynyl, C 1-6 alkoxy-C 1-4 alkyl, C 1-4 alkylthio-C 1-4 alkyl or benzyl; Z represents oxygen or sulfur; X and Y independently represent halogen, C 1-6 alkyl or C 1-4 haloalkyl; m and n are independently an integer of 1 to 3; and m X's and n Y's may be the same or different, respectively, the process comprising reacting an α-substituted-phenylacetonitrile compound represented by the formula (2):
wherein R 1 , X and m are as defined above, with a benzoyl halide represented by the formula (3):
wherein Y and n are as defined above, and R 3 represents halogen.
7. A miticide comprising as an active ingredient an acylacetonitrile compound represented by the formula (1):
wherein R 1 represents —C(O)ZR 2 ; R 2 represents C 1-6 alkyl, C 1-4 haloalkyl, C 2-4 alkenyl, C 2-4 alkynyl, C 1-6 alkoxy-C 1-4 alkyl, C 1-4 alkylthio-C 1-4 alkyl or benzyl; Z represents oxygen or sulfur; X and Y independently represent halogen, C 1-6 alkyl or C 1-4 haloalkyl; m and n are independently an integer of 1 to 3; and m X's and n Y's may be the same or different, respectively.
8. A miticide according to claim 7 , wherein Z in the formula (1) represents oxygen.
9. A miticide according to claim 7 , wherein X in the formula (1) represents halogen or C 1-6 alkyl.
10. A miticide according to claim 7 , wherein Y in the formula (1) represents at least one species selected from halogen and C 1-4 haloalkyl.
11. A miticide according to claim 7 , wherein Z represents oxygen, X represents C 1-6 alkyl, and Y represents C 1-4 haloalkyl in the formula (1).
12. A miticide according to any of claim 7 , which is effective against plant-parasitic mites.
13. A method for exterminating mites comprising applying to the site an acylacetonitrile compound represented by the formula (1):
wherein R 1 represents —C(O)ZR 2 ; R 2 represents C 1-6 alkyl, C 1-4 haloalkyl, C 2-4 alkenyl, C 2-4 alkynyl, C 1-6 alkoxy-C 1-4 alkyl, C 1-4 alkylthio-C 1-4 alkyl or benzyl; Z represents oxygen or sulfur; X and Y independently represent halogen, C 1-6 alkyl or C 1-4 haloalkyl; m and n are independently an integer of 1 to 3; and m X's and n Y's may be the same or different, respectively.
14. A method for producing a miticide, said method comprising producing said miticide by using on acylacetonitrile compound represented by the formula (1):
wherein R 1 represents —C(O)ZR 2 ; R 2 represents C 1-6 alkyl, C 1-4 haloalkyl, C 2-4 alkenyl, C 2-4 alkynyl, C 1-6 alkoxy-C 1-4 alkyl, C 1-4 alkylthio-C 1-4 alkyl or benzyl; Z represents oxygen or sulfur; X and Y independently represent halogen, C 1-6 alkyl or C 1-4 haloalkyl; m and n are independently an integer of 1 to 3; and m X's and n Y's may be the same or different, respectively.
15. An acylacetonitrile compound according to claim 2 , wherein X in the formula (1) represents halogen or C 1-6 alkyl.
16. An acylacitonitrile compound according to claim 2 , wherein Y in the formula (1) represents at least one species selected form halogen and C 1-4 haloalkyl.
17. A miticide according to claim 8 , wherein X in the formula (1) represents halogen or C 1-6 alkyl.
18. A miticide according to calim 8 , wherein Y in the formula (1) represents at least one species selected from halogen and C 1-4 haloalkyl.
19. Amiticide according to claim 11 , which is effective against plant-parasitic mites.