US 12,741,967 B2 · Condensed heterocyclic compound having a sulfonamide group or salt thereof, agricultural or horticultural insecticide or animal ectoparasite or endoparasite control agent comprising the compound or the salt thereof, and method for using the compound or the salt thereof, the insecticide, or the control agent

Abstract

An object of the present invention is to provide a novel agricultural or horticultural insecticide and a novel animal ectoparasite or endoparasite control agent in order to solve problems in crop production in the fields of agriculture, horticulture and the like, such as immense damage caused by insect pests, etc. and the emergence of insecticide-resistant pests. The object can be achieved by a condensed heterocyclic compound having a sulfonamide group represented by the general formula (1): or a salt thereof, an agricultural or horticultural insecticide containing the compound or the salt thereof as an active ingredient, an animal ectoparasite or endoparasite control agent containing the compound or the salt thereof as an active ingredient, and a method for using the compound or the salt thereof, the insecticide, or the control agent.

A condensed heterocyclic compound having a sulfonamide group represented by the general formula (1):

wherein
R1 and R2 may be the same or different and each represent
(a1) a hydrogen atom;
or
(a2) a (C1-C6) alkyl group;
or
(a3) R1 and R2 may join together to form a 3- to 6-membered aliphatic ring having the nitrogen atom of the sulfonamide group,
X1 represents
(b1) a hydrogen atom;
(b2) a halo (C1-C6) alkyl group;
(b3) a halo (C1-C6) alkoxy group;
(b4) a halo (C1-C6) alkylthio group;
(b5) a halo (C1-C6) alkylsulfinyl group;
or
(b6) a halo (C1-C6) alkylsulfonyl group,
Y1 represents
(c1) a hydrogen atom;
(c2) a halogen atom;
(c3) a (C1-C6) alkyl group;
(c4) a (C3-C6) cycloalkyl group;
(c5) a cyano (C3-C6) cycloalkyl group;
(c6) an aryl group;
(c7) an aryl group having, on the ring, 1 to 5 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 (C1-C6) alkyl group, (e) a halo (C1-C6) alkyl group, (f) a (C1-C6) alkoxy group, (g) a halo (C1-C6) alkoxy group, (h) a (C1-C6) alkylthio group, (i) a halo (C1-C6) alkylthio group, (j) a (C1-C6) alkylsulfinyl group, (k) a halo (C1-C6) alkylsulfinyl group, (1) a (C1-C6) alkylsulfonyl group, and
(m) a halo (C1-C6) alkylsulfonyl group;
or
(c8) a triazole group,
Y2 represents
(d1) a hydrogen atom;
(d2) a (C3-C6) cycloalkyl group;
(d3) a cyano (C3-C6) cycloalkyl group;
(d4) a halo (C1-C6) alkyl group;
(d5) a C (R3)=NOR4 group wherein R3 represents a (C3-C6) cycloalkyl group, and R4 represents a halo (C1-C6) alkyl group;
(d6) an aryl group;
(d7) an aryl group having, on the ring, 1 to 5 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 (C1-C6) alkyl group, (e) a halo (C1-C6) alkyl group, (f) a (C1-C6) alkoxy group, (g) a halo (C1-C6) alkoxy group, (h) a (C1-C6) alkylthio group, (i) a halo (C1-C6) alkylthio group, (j) a (C1-C6) alkylsulfinyl group, (k) a halo (C1-C6) alkylsulfinyl group, (1) a (C1-C6) alkylsulfonyl group, (m) a halo (C1-C6) alkylsulfonyl group, (k) a (C1-C6) alkylthio group, (1) a formyl group, (m) a (C1-C6) alkylcarbonyl group, (n) a (C1-C6) alkoxycarbonyl group, (o) an acetamide group, (p) a methylene dioxy group, and (q) a trimethylsilyl group;
(d8) Y1 and Y2 may join together with the pyridine ring bound to Y1 and Y2 to form an aromatic heterocyclic ring in which the aromatic ring moiety is an aromatic heterocyclic group optionally having, on the ring, 1 to 4 substituting groups selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C1-C6) alkyl group, (e) a halo (C1-C6) alkyl group, (f) a (C1-C6) alkoxy group, (g) a halo (C1-C6) alkoxy group, (h) a (C1-C6) alkylthio group, (i) a halo (C1-C6) alkylthio group, (j) a (C1-C6) alkylsulfinyl group, (k) a halo (C1-C6) alkylsulfinyl group, (1) a (C1-C6) alkylsulfonyl group, and (m) a halo (C1-C6) alkylsulfonyl group;
(d9) a halogen atom;
(d10) a (C1-C6) alkyl group;
(d11) a (C2-C6) alkenyl group;
(d12) a (C1-C6) alkoxy group;
(d13) a halo (C1-C6) alkoxy group;
(d14) a (C1-C6) alkylthio group;
(d15) a (C1-C6) alkylsulfonyl group;
(d16) a carboxyl group;
(d17) a (C1-C6) alkoxycarbonyl group;
(d18) a cyano (C1-C6) alkyl group;
(d19) a cyano halo (C1-C6) alkyl group;
(d20) a (C1-C6) alkoxy (C1-C6) alkyl group;
(d21) a (C1-C6) alkylsulfonyl (C1-C6) alkyl group;
(d22) an NRaRb group wherein Ra and Rb may be the same or different and each represent
(aa) a hydrogen atom,
(ab) a (C1-C6) alkyl group,
(ac) a (C2-C6) alkynyl group,
(ad) a (C3-C6) cycloalkyl (C1-C6) alkyl group,
(ae) a (C1-C6) alkoxy (C1-C6) alkyl group,
(af) a (C1-C6) alkylcarbonyl group,
(ag) a (C1-C6) alkoxycarbonyl group, or
(ah) a dimethylaminocarbonyl group;
(d23) a CONRaRb group wherein Ra and Rb are the same as above;
(d24) a dimethylamino (C1-C6) alkylideneamino group;
(d25) a dimethylsulfinylideneamino group;
(d26) a pyrimidyl group;
(d27) a pyrimidyl 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 (C1-C6) alkyl group, (e) a halo (C1-C6) alkyl group, (f) a (C1-C6) alkoxy group, (g) a halo (C1-C6) alkoxy group, (h) a (C1-C6) alkylthio group, (i) a halo (C1-C6) alkylthio group, (j) a (C1-C6) alkylsulfinyl group, (k) a halo (C1-C6) alkylsulfinyl group, (1) a (C1-C6) alkylsulfonyl group, and
(m) a halo (C1-C6) alkylsulfonyl group;
(d28) a pyridyl group;
(d29) a pyridyl group having, on the ring, 1 to 4 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 (C1-C6) alkyl group, (e) a halo (C1-C6) alkyl group, (f) a (C1-C6) alkoxy group, (g) a halo (C1-C6) alkoxy group, (h) a (C1-C6) alkylthio group, (i) a halo (C1-C6) alkylthio group, (j) a (C1-C6) alkylsulfinyl group, (k) a halo (C1-C6) alkylsulfinyl group, (1) a (C1-C6) alkylsulfonyl group, and
(m) a halo (C1-C6) alkylsulfonyl group;
(d30) a pyridazinyl group;
(d31) a pyridazinyl 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 (C1-C6) alkyl group, (e) a halo (C1-C6) alkyl group, (f) a (C1-C6) alkoxy group, (g) a halo (C1-C6) alkoxy group, (h) a (C1-C6) alkylthio group, (i) a halo (C1-C6) alkylthio group, (j) a (C1-C6) alkylsulfinyl group, (k) a halo (C1-C6) alkylsulfinyl group, (1) a (C1-C6) alkylsulfonyl group, and
(m) a halo (C1-C6) alkylsulfonyl group;
(d32) a pyrazinyl group;
(d33) a pyrazinyl 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 (C1-C6) alkyl group, (e) a halo (C1-C6) alkyl group, (f) a (C1-C6) alkoxy group, (g) a halo (C1-C6) alkoxy group, (h) a (C1-C6) alkylthio group, (i) a halo (C1-C6) alkylthio group, (j) a (C1-C6) alkylsulfinyl group, (k) a halo (C1-C6) alkylsulfinyl group, (1) a (C1-C6) alkylsulfonyl group, and
(m) a halo (C1-C6) alkylsulfonyl group;
(d34) a furanyl group;
(d35) a furanyl 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 (C1-C6) alkyl group, (e) a halo (C1-C6) alkyl group, (f) a (C1-C6) alkoxy group, (g) a halo (C1-C6) alkoxy group, (h) a (C1-C6) alkylthio group, (i) a halo (C1-C6) alkylthio group, (j) a (C1-C6) alkylsulfinyl group, (k) a halo (C1-C6) alkylsulfinyl group, (1) a (C1-C6) alkylsulfonyl group, and
(m) a halo (C1-C6) alkylsulfonyl group;
(d36) a thienyl group;
(d37) a thienyl 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 (C1-C6) alkyl group, (e) a halo (C1-C6) alkyl group, (f) a (C1-C6) alkoxy group, (g) a halo (C1-C6) alkoxy group, (h) a (C1-C6) alkylthio group, (i) a halo (C1-C6) alkylthio group, (j) a (C1-C6) alkylsulfinyl group, (k) a halo (C1-C6) alkylsulfinyl group, (1) a (C1-C6) alkylsulfonyl group, and
(m) a halo (C1-C6) alkylsulfonyl group;
(d38) an imidazole group;
(d39) an imidazole 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 (C1-C6) alkyl group, (e) a halo (C1-C6) alkyl group, (f) a (C1-C6) alkoxy group, (g) a halo (C1-C6) alkoxy group, (h) a (C1-C6) alkylthio group, (i) a halo (C1-C6) alkylthio group, (j) a (C1-C6) alkylsulfinyl group, (k) a halo (C1-C6) alkylsulfinyl group, (1) a (C1-C6) alkylsulfonyl group, and
(m) a halo (C1-C6) alkylsulfonyl group;
(d40) a pyrazole group;
(d41) a pyrazole 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 (C1-C6) alkyl group, (e) a halo (C1-C6) alkyl group, (f) a (C1-C6) alkoxy group, (g) a halo (C1-C6) alkoxy group, (h) a (C1-C6) alkylthio group, (i) a halo (C1-C6) alkylthio group, (j) a (C1-C6) alkylsulfinyl group, (k) a halo (C1-C6) alkylsulfinyl group, (1) a (C1-C6) alkylsulfonyl group, and (m) a halo (C1-C6) alkylsulfonyl group;
(d42) a thiazole group;
(d43) a thiazole 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 (C1-C6) alkyl group, (e) a halo (C1-C6) alkyl group, (f) a (C1-C6) alkoxy group, (g) a halo (C1-C6) alkoxy group, (h) a (C1-C6) alkylthio group, (i) a halo (C1-C6) alkylthio group, (j) a (C1-C6) alkylsulfinyl group, (k) a halo (C1-C6) alkylsulfinyl group, (1) a (C1-C6) alkylsulfonyl group, and (m) a halo (C1-C6) alkylsulfonyl group;
(d44) an isothiazole group;
(d45) an isothiazole 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 (C1-C6) alkyl group, (e) a halo (C1-C6) alkyl group, (f) a (C1-C6) alkoxy group, (g) a halo (C1-C6) alkoxy group, (h) a (C1-C6) alkylthio group, (i) a halo (C1-C6) alkylthio group, (j) a (C1-C6) alkylsulfinyl group, (k) a halo (C1-C6) alkylsulfinyl group, (1) a (C1-C6) alkylsulfonyl group, and (m) a halo (C1-C6) alkylsulfonyl group;
(d46) an oxazole group;
(d47) an oxazole 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 (C1-C6) alkyl group, (e) a halo (C1-C6) alkyl group, (f) a (C1-C6) alkoxy group, (g) a halo (C1-C6) alkoxy group, (h) a (C1-C6) alkylthio group, (i) a halo (C1-C6) alkylthio group, (j) a (C1-C6) alkylsulfinyl group, (k) a halo (C1-C6) alkylsulfinyl group, (1) a (C1-C6) alkylsulfonyl group, and (m) a halo (C1-C6) alkylsulfonyl group;
(d48) an isoxazole group;
(d49) an isoxazole 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 (C1-C6) alkyl group, (e) a halo (C1-C6) alkyl group, (f) a (C1-C6) alkoxy group, (g) a halo (C1-C6) alkoxy group, (h) a (C1-C6) alkylthio group, (i) a halo (C1-C6) alkylthio group, (j) a (C1-C6) alkylsulfinyl group, (k) a halo (C1-C6) alkylsulfinyl group, (1) a (C1-C6) alkylsulfonyl group, and (m) a halo (C1-C6) alkylsulfonyl group;
(d50) an oxadiazole group;
(d51) an oxadiazole group having, on the ring, one substituting group which may be the same or different and is selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C1-C6) alkyl group, (e) a halo (C1-C6) alkyl group, (f) a (C1-C6) alkoxy group, (g) a halo (C1-C6) alkoxy group, (h) a (C1-C6) alkylthio group, (i) a halo (C1-C6) alkylthio group, (j) a (C1-C6) alkylsulfinyl group, (k) a halo (C1-C6) alkylsulfinyl group, (1) a (C1-C6) alkylsulfonyl group, and (m) a halo (C1-C6) alkylsulfonyl group;
(d52) a thiadiazole group;
(d53) a thiadiazole group having, on the ring, one substituting group which may be the same or different and is selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C1-C6) alkyl group, (e) a halo (C1-C6) alkyl group, (f) a (C1-C6) alkoxy group, (g) a halo (C1-C6) alkoxy group, (h) a (C1-C6) alkylthio group, (i) a halo (C1-C6) alkylthio group, (j) a (C1-C6) alkylsulfinyl group, (k) a halo (C1-C6) alkylsulfinyl group, (1) a (C1-C6) alkylsulfonyl group, and (m) a halo (C1-C6) alkylsulfonyl group;
(d54) a triazole group;
(d55) 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 (C1-C6) alkyl group, (e) a halo (C1-C6) alkyl group, (f) a (C1-C6) alkoxy group, (g) a halo (C1-C6) alkoxy group, (h) a (C1-C6) alkylthio group, (i) a halo (C1-C6) alkylthio group, (j) a (C1-C6) alkylsulfinyl group, (k) a halo (C1-C6) alkylsulfinyl group, (1) a (C1-C6) alkylsulfonyl group, and (m) a halo (C1-C6) alkylsulfonyl group;
(d56) a pyrimidyloxy group;
(d57) a pyridyloxy group;
or
the following structural formula Q1, Q2, Q3, Q4, Q5, or Q6:
wherein R5s may be the same or different and each represent a halogen atom or a (C1-C6) alkyl group;
R6 represents a (C1-C6) alkyl group;
m represents an integer of 0 to 2, and the arrow represents a binding position,
G1 represents an oxygen atom, a nitrogen atom, CH, CF, or N—CH3,
G2 represents a carbon atom or a nitrogen atom,
G3 represents a nitrogen atom or CH, and
G4 represents a nitrogen atom or a C—X2 group, wherein X2 represents a hydrogen atom or a halo (C1-C6) alkyl group, or
a salt thereof.

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Life of this patent

Life of this patent

Abstract

Claims9