US 10,292,395 B2 · 3H-pyrrolopyridine compound, N-oxide thereof or salt thereof, agricultural and horticultural insecticide comprising the compound and method for using the same

Abstract

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. Under such circumstances, the development of novel agricultural and horticultural insecticides is desired. The present invention provides an agricultural and horticultural insecticide comprising, as an active ingredient, a 3H-pyrrolopyridine compound represented by the general formula (1): (wherein A1, A2, and A3 each represent a nitrogen atom or a CH group, R1 represents an ethyl group, R2 and R4 each represent a hydrogen atom, R3 and R7 each represent a haloalkyl group, R5 and R6 each represent a fluorine atom, and m represents 0 or 2), an N-oxide thereof or a salt thereof; and a method for using the agricultural and horticultural insecticide.

A 3H-pyrrolopyridine compound represented by the general formula (1):

wherein:
R1 represents:
(a1) a (C1-C6) alkyl group;
(a2) a (C3-C6) cycloalkyl group;
(a3) a (C2-C6) alkenyl group;
or
(a4) a (C2-C6) alkynyl group,
R2 and R4 may be the same or different and each represent:
(b1) a hydrogen atom;
(b2) a halogen atom;
(b3) a hydroxyl group;
(b4) a formyl group;
(b5) a cyano group;
(b6) a (C1-C6) alkyl group;
(b7) a (C3-C6) cycloalkyl group;
(b8) a (C1-C6) alkoxy group;
(b9) a halo (C1-C6) alkyl group;
(b10) a halo (C3-C6) cycloalkyl group;
(b11) a halo (C1-C6) alkoxy group;
(b12) a (C1-C6) alkylthio group;
(b13) a (C1-C6) alkylsulfinyl group;
(b14) a (C1-C6) alkylsulfonyl group;
(b15) a halo (C1-C6) alkylthio group;
(b16) a halo (C1-C6) alkylsulfinyl group;
(b17) a halo (C1-C6) alkylsulfonyl group;
(b18) a (C3-C6) cycloalkyl (C1-C6) alkoxy group;
(b19) a R9(R10)N group (wherein R9 and R10 may be the same or different and each represent a hydrogen atom, a (C1-C6) alkyl group, a (C3-C6) cycloalkyl (C1-C6) alkyl group, a halo (C1-C6) alkyl group, a (C1-C6) alkylcarbonyl group, a (C1-C6) alkoxycarbonyl group or a phenylcarbonyl group);
(b20) a mono-(C1-C6) alkylaminocarbonyl NH group;
(b21) a mono-(C1-C6) alkylaminothiocarbonyl NH group;
(b22) a C(R9)═NOR10 group (wherein R9 and R10 are as defined above);
(b23) a carboxyl group;
(b24) a (C1-C6) alkoxycarbonyl group;
(b25) a R9(R10)N carbonyl group (wherein R9 and R10 are as defined above);
(b26) an aryl group;
(b27) an aryl group having, on the ring, 1 to 5 substituting groups which may be the same or different and are selected from the group consisting of a halogen atom, a (C1-C6) alkyl group, a halo (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo (C1-C6) alkoxy group, a (C1-C6) alkylthio group, a halo (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a halo (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group and a halo (C1-C6) alkylsulfonyl group;
(b28) an aryl (C1-C6) alkyl group;
(b29) an aryl (C1-C6) alkyl group having, on the ring, 1 to 5 substituting groups which may be the same or different and are selected from the group consisting of a halogen atom, a (C1-C6) alkyl group, a halo (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo (C1-C6) alkoxy group, a (C1-C6) alkylthio group, a halo (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a halo (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group and a halo (C1-C6) alkylsulfonyl group;
(b30) an aryl (C1-C6) alkyloxy group;
(b31) an aryl (C1-C6) alkyloxy group having, on the ring, 1 to 5 substituting groups which may be the same or different and are selected from the group consisting of a halogen atom, a (C1-C6) alkyl group, a halo (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo (C1-C6) alkoxy group, a (C1-C6) alkylthio group, a halo (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a halo (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group and a halo (C1-C6) alkylsulfonyl group;
(b32) an aryl (C1-C6) alkyl NH group;
(b33) an aryl (C1-C6) alkyl NH group having, on the ring, 1 to 5 substituting groups which may be the same or different and are selected from the group consisting of a halogen atom, a (C1-C6) alkyl group, a halo (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo (C1-C6) alkoxy group, a (C1-C6) alkylthio group, a halo (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a halo (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group and a halo (C1-C6) alkylsulfonyl group;
(b34) a heterocyclic group;
or
(b35) a heterocyclic group having, on the ring, 1 to 3 substituting groups which may be the same or different and are selected from the group consisting of a halogen atom, a (C1-C6) alkyl group, a halo (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo (C1-C6) alkoxy group, a (C1-C6) alkylthio group, a halo (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a halo (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group and a halo (C1-C6) alkylsulfonyl group,
R3 and R7 may be the same or different and each represent:
(c1) a hydrogen atom;
(c2) a halogen atom;
(c3) a hydroxyl group;
(c4) a formyl group;
(c5) a cyano group;
(c6) a (C1-C6) alkyl group;
(c7) a (C3-C6) cycloalkyl group;
(c8) a (C1-C6) alkoxy group;
(c9) a halo (C1-C6) alkyl group;
(c10) a halo (C3-C6) cycloalkyl group;
(c11) a halo (C1-C6) alkoxy group;
(c12) a (C1-C6) alkylthio group;
(c13) a (C1-C6) alkylsulfinyl group;
(c14) a (C1-C6) alkylsulfonyl group;
(c15) a halo (C1-C6) alkylthio group;
(c16) a halo (C1-C6) alkylsulfinyl group;
(c17) a halo (C1-C6) alkylsulfonyl group;
(c18) a (C3-C6) cycloalkyl (C1-C6) alkoxy group;
(c19) a R9(R10)N group (wherein R9 and R10 are as defined above);
(c20) a mono-(C1-C6) alkylaminocarbonyl NH group;
(c21) a mono-(C1-C6) alkylaminothiocarbonyl NH group;
(c22) a C(R9)═NOR10 group (wherein R9 and R10 are as defined above);
(c23) a carboxyl group;
(c24) a (C1-C6) alkoxycarbonyl group;
(c25) a R9(R10)N carbonyl group (wherein R9 and R10 are as defined above);
(c26) an aryl group;
(c27) an aryl group having, on the ring, 1 to 5 substituting groups which may be the same or different and are selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a halo (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo (C1-C6) alkoxy group, a (C1-C6) alkylthio group, a halo (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a halo (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group and a halo (C1-C6) alkylsulfonyl group;
(c28) an aryl (C1-C6) alkyl group;
(c29) an aryl (C1-C6) alkyl group having, on the ring, 1 to 5 substituting groups which may be the same or different and are selected from the group consisting of a halogen atom, a (C1-C6) alkyl group, a halo (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo (C1-C6) alkoxy group, a (C1-C6) alkylthio group, a halo (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a halo (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group and a halo (C1-C6) alkylsulfonyl group;
(c30) an aryl (C1-C6) alkyloxy group;
(c31) an aryl (C1-C6) alkyloxy group having, on the ring, 1 to 5 substituting groups which may be the same or different and are selected from the group consisting of a halogen atom, a (C1-C6) alkyl group, a halo (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo (C1-C6) alkoxy group, a (C1-C6) alkylthio group, a halo (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a halo (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group and a halo (C1-C6) alkylsulfonyl group;
(c32) an aryl (C1-C6) alkyl NH group;
(c33) an aryl (C1-C6) alkyl NH group having, on the ring, 1 to 5 substituting groups which may be the same or different and are selected from the group consisting of a halogen atom, a (C1-C6) alkyl group, a halo (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo (C1-C6) alkoxy group, a (C1-C6) alkylthio group, a halo (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a halo (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group and a halo (C1-C6) alkylsulfonyl group;
(c34) a heterocyclic group;
or
(c35) a heterocyclic group having, on the ring, 1 to 3 substituting groups which may be the same or different and are selected from the group consisting of a halogen atom, a (C1-C6) alkyl group, a halo (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo (C1-C6) alkoxy group, a (C1-C6) alkylthio group, a halo (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a halo (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group and a halo (C1-C6) alkylsulfonyl group,
R5 and R6 may be the same or different and each represent:
(d1) a halogen atom;
(d2) a cyano group;
(d3) a (C1-C6) alkyl group;
(d4) a (C1-C6) alkylthio group;
(d5) a (C1-C6) alkylsulfonyl group;
or
(d6) a (C1-C6) alkoxycarbonyl group, or alternatively
(d7) R5 and R6 are joined together to form a 3- to 6-membered aliphatic ring,
R3 and R4 may be combined to form an aromatic ring,
A1, A2 and A3 may be the same or different and each represent a nitrogen atom, N—O or a C—R8 group (wherein R8 represents (e1) a hydrogen atom;
or (e2) a halogen atom), and
m represents 0, 1 or 2,
an N-oxide thereof or a salt thereof.

92 more elements

3H-pyrrolopyridine compound, N-oxide thereof or salt thereof, agricultural and horticultural insecticide comprising the compound and method for using the same

Life of this patent

3H-pyrrolopyridine compound, N-oxide thereof or salt thereof, agricultural and horticultural insecticide comprising the compound and method for using the same

Life of this patent

Abstract

Claims7