Oxime group-containing condensed heterocyclic compound or salt thereof, agricultural and horticultural insecticide comprising the compound or the salt, and method for using the insecticide
In crop production in the fields of agriculture, horticulture and the like, the damage caused by insect pests etc. is still immense, and insect pests resistant to existing insecticides have emerged. The present invention has been made in view of such circumstances, and an object of the present invention is to develop and provide a novel agricultural and horticultural insecticide. The present invention provides an oxime group-containing condensed heterocyclic compound represented by the general formula (1): {wherein R 1 represents an alkoxy group, R 2 represents a haloalkyl group, R 3 represents a haloalkylthio group, A represents an oxygen atom, A 1 represents a CH group, m represents 2, and n represents 1}, or a salt thereof; an agricultural and horticultural insecticide comprising the compound or the salt as an active ingredient; and a method for using the insecticide.
1. An oxime group-containing condensed heterocyclic compound represented by the general formula (1):
wherein
R 1 represents:
(a1) a halogen atom;
(a2) a (C 1 -C 6 ) alkoxy group;
(a3) a (C 2 -C 6 ) alkenyloxy group;
(a4) a (C 2 -C 6 ) alkynyloxy group;
(a5) a (C 1 -C 6 ) alkylthio group;
(a6) a (C 2 -C 6 ) alkenylthio group;
(a7) a (C 2 -C 6 ) alkynylthio group;
(a8) an imidazole group;
(a9) an imidazole group having, on the ring, 1 to 3 substituting groups which may be the same or different and are selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C 1 -C 6 ) alkyl group, (f) a halo (C 1 -C 6 ) alkyl group, (g) a (C 1 -C 6 ) alkoxy group, (h) a halo (C 1 -C 6 ) alkoxy group, (i) a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkoxy group, (j) a (C 1 -C 6 ) alkylthio group, (k) a halo (C 1 -C 6 ) alkylthio group, (1) a (C 1 -C 6 ) alkylsulfinyl group, (m) a halo (C 1 -C 6 ) alkylsulfinyl group, (n) a (C 1 -C 6 ) alkylsulfonyl group or (o) a halo (C 1 -C 6 ) alkylsulfonyl group;
(a10) a triazole group;
(a11) a triazole group having, on the ring, 1 or 2 substituting groups which may be the same or different and are selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C 1 -C 6 ) alkyl group, (f) a halo (C 1 -C 6 ) alkyl group, (g) a (C 1 -C 6 ) alkoxy group, (h) a halo (C 1 -C 6 ) alkoxy group, (i) a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkoxy group, (j) a (C 1 -C 6 ) alkylthio group, (k) a halo (C 1 -C 6 ) alkylthio group, (1) a (C 1 -C 6 ) alkylsulfinyl group, (m) a halo (C 1 -C 6 ) alkylsulfinyl group, (n) a (C 1 -C 6 ) alkylsulfonyl group or (o) a halo (C 1 -C 6 ) alkylsulfonyl group;
(a12) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group;
(a13) a (C 1 -C 6 ) alkylcarbonylamino group;
(a14) a (C 1 -C 6 ) alkoxycarbonylamino group;
(a15) a (C 1 -C 6 ) alkylcarbonyl ((C 1 -C 6 ) alkyl)amino group; or
(a16) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkoxy group,
R 2 represents:
(b1) a hydrogen atom;
(b2) a (C 1 -C 6 ) alkyl group;
(b3) a (C 2 -C 6 ) alkenyl group;
(b4) a (C 2 -C 6 ) alkynyl group;
(b5) a (C 3 -C 6 ) cycloalkyl group;
(b6) a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group;
(b7) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group;
(b8) a halo (C 1 -C 6 ) alkyl group;
(b9) a halo (C 2 -C 6 ) alkenyl group;
(b10) a halo (C 2 -C 6 ) alkynyl group; or
(b11) a (C 1 -C 6 ) alkylthio (C 1 -C 6 ) alkyl group,
R 3 represents:
(c1) a halogen atom;
(c2) a halo (C 1 -C 6 ) alkyl group;
(c3) a halo (C 1 -C 6 ) alkoxy group;
(c4) a halo (C 1 -C 6 ) alkylthio group;
(c5) a halo (C 1 -C 6 ) alkylsulfinyl group; or
(c6) a halo (C 1 -C 6 ) alkylsulfonyl group,
A represents an oxygen atom or N—R 4 wherein
R 4 represents:
(e1) a (C 1 -C 6 ) alkyl group;
(e2) a (C 3 -C 6 ) cycloalkyl group;
(e3) a (C 2 -C 6 ) alkenyl group; or
(e4) a (C 2 -C 6 ) alkynyl group,
A 1 represents a CH group or a nitrogen atom,
m represents 0, 1 or 2, and
n represents 0, 1 or 2,
or a salt thereof.
2. The oxime group-containing condensed heterocyclic compound or the salt according to claim 1 , wherein A is an oxygen atom and A 1 is a CH group.
3. The oxime compound or the salt according to claim 1 , wherein A is N—R 4 and wherein R 4 is as defined above.
4. An agricultural or horticultural insecticide comprising the oxime group-containing condensed heterocyclic compound or the salt according to claim 1 as an active ingredient.
5. An animal ectoparasite control agent comprising the oxime group-containing condensed heterocyclic compound or the salt according to claim 1 as an active ingredient.
6. A method for using an agricultural or horticultural insecticide, comprising contacting plants or soil with an effective amount of the oxime group-containing condensed heterocyclic compound or the salt according to claim 1 .
7. A method for controlling agricultural or horticultural insects comprising contacting agricultural or horticultural insects with an effective amount of the agricultural or horticultural insecticide according to claim 4 .
8. A method for controlling animal ectoparasites comprising contacting animal ectoparasites with an effective amount of the animal ectoparasite control agent of claim 5 .