US 10,306,885 B2 · Anthranilic acid ester compound or salt thereof, agricultural and horticultural microbicide comprising the compound, and method for using the microbicide

Abstract

In crop production in the fields of agriculture, horticulture and the like, the damage caused by diseases etc. is still immense, and diseases resistant to existing microbicides have emerged. Under such circumstances, the development of novel agricultural and horticultural microbicides is desired. The present invention provides an anthranilic acid ester compound represented by the general formula (1): (wherein A1, A3 and A4 each represent a CH group, A2 represents a C-haloalkyl group, R1 represents an alkyl group, R3 represents a hydrogen atom or an acyl group, R4, R5 and R7 each represent a hydrogen atom, R6 represents a haloalkyl group, Z represents an alkyl group, and m represents 0, 1 or 2), or a salt thereof, an agricultural and horticultural microbicide comprising the compound or a salt thereof as an active ingredient, and a method for using the microbicide.

An anthranilic acid ester compound or a salt thereof wherein the compound represented by the formula (1):

wherein R1 represents:
(a1) a (C1-C6) alkyl group;
(a2) a (C2-C6) alkenyl group;
(a3) a (C2-C6) alkynyl group;
(a4) a (C3-C6) cycloalkyl (C1-C6) alkyl group;
(a5) a phenyl group;
or
(a6) a phenyl 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) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C1-C6) alkyl group, (e) a (C1-C6) alkoxy group, (f) a halo (C1-C6) alkyl group and (g) a halo (C1-C6) alkoxy group,
R3 represents:
(b1) a hydrogen atom;
(b2) a (C1-C6) alkyl group;
(b3) a (C2-C6) alkenyl group;
(b4) a (C2-C6) alkynyl group;
(b5) a (C3-C6) cycloalkyl group;
(b6) a halo (C1-C6) alkyl group;
(b7) a (C3-C6) cycloalkyl (C1-C6) alkyl group;
(b8) a (C1-C6) alkoxy (C1-C6) alkyl group;
(b9) a (C1-C6) alkylcarbonyl group;
(b10) a (C1-C6) alkoxycarbonyl group;
(b11) a (C3-C6) cycloalkylcarbonyl group;
(b12) a (C1-C6) alkoxy (C1-C6) alkylcarbonyl group;
(b13) a halo (C1-C6) alkylcarbonyl group;
(b14) a (C1-C6) alkoxycarbonyl (C1-C6) alkyl group;
or
(b15) a (C1-C6) alkoxy group,
R4, R5, R6 and R7 may be the same or different, and each represent:
(c1) a hydrogen atom;
(c2) a halogen atom;
(c3) a cyano group;
(c4) a nitro group;
(c5) a (C1-C6) alkyl group;
(c6) a halo (C1-C6) alkyl group;
(c7) a (C3-C6) cycloalkyl group;
(c8) a halo (C3-C6) cycloalkyl group;
(c9) a (C1-C6) alkoxy group;
(c10) a halo (C1-C6) alkoxy group;
(c11) a (C1-C6) alkylthio group;
(c12) a (C1-C6) alkylsulfinyl group;
(c13) a (C1-C6) alkylsulfonyl group;
(c14) a halo (C1-C6) alkylthio group;
(c15) a halo (C1-C6) alkylsulfinyl group;
(c16) a halo (C1-C6) alkylsulfonyl group;
(c17) a (C1-C6) alkoxy halo (C1-C6) alkyl group;
(c18) a phenyl group;
(c19) a phenyl 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) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C1-C6) alkyl group, (e) a (C1-C6) alkoxy group, (f) a halo (C1-C6) alkyl group and (g) a halo (C1-C6) alkoxy group;
(c20) a phenoxy group;
(c21) a phenoxy 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) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C1-C6) alkyl group, (e) a (C1-C6) alkoxy group, (f) a halo (C1-C6) alkyl group and (g) a halo (C1-C6) alkoxy group;
(c22) a pyridyloxy group;
(c23) a pyridyloxy group having, on the ring, 1 to 4 substituting groups which may be the same or different and are selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C1-C6) alkyl group, (e) a (C1-C6) alkoxy group, (f) a halo (C1-C6) alkyl group and (g) a halo (C1-C6) alkoxy group;
(c24) an amino group;
(c25) an amino group having 1 to 2 substituting groups which may be the same or different and are selected from the group consisting of (d) a (C1-C6) alkyl group, (e) a (C1-C6) alkoxy group, (f) a halo (C1-C6) alkyl group and (g) a halo (C1-C6) alkoxy group;
(c26) a phenyl (C1-C6) alkoxy group;
or
(c27) a phenyl (C1-C6) alkoxy 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) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C1-C6) alkyl group, (e) a (C1-C6) alkoxy group, (f) a halo (C1-C6) alkyl group and (g) a halo (C1-C6) alkoxy group,
except for a case where R4, R5, R6 and R7 each represent a hydrogen atom,
A1 and A3 each represent a C—H group,
A4 represents a nitrogen atom or a C—H group,
A2 represents a C—R2 group (wherein R2 represents:
(d2) a halogen atom;
(d3) a (C1-C6) alkyl group;
(d4) a (C1-C6) alkoxy group;
(d5) a halo (C1-C6) alkyl group;
(d6) a halo (C1-C6) alkoxy group;
(d7) a (C1-C6) alkylthio group;
(d8) a (C1-C6) alkylsulfinyl group;
(d9) a (C1-C6) alkylsulfonyl group;
(d10) a halo (C1-C6) alkylthio group;
(d11) a halo (C1-C6) alkylsulfinyl group;
(d12) a halo (C1-C6) alkylsulfonyl group;
(d13) a cyclo (C3-C6) alkyl group;
(d14) a phenyl group;
(d15) a phenyl 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) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C1-C6) alkyl group, (e) a (C1-C6) alkoxy group, (f) a halo (C1-C6) alkyl group and (g) a halo (C1-C6) alkoxy group;
or
(d16) a phenoxy group),
Z represents:
(e1) a (C1-C6) alkyl group;
(e2) a (C2-C6) alkenyl group;
(e3) a (C3-C6) alkynyl group;
(e4) a (C3-C6) cycloalkyl group;
(e5) a cyclo (C3-C6) alkyl (C1-C6) alkyl group;
(e6) a phenyl (C1-C6) alkyl group;
or
(e7) a cyano (C1-C6) alkyl group, and
m represents 0, 1 or 2.

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Anthranilic acid ester compound or salt thereof, agricultural and horticultural microbicide comprising the compound, and method for using the microbicide

Life of this patent

Anthranilic acid ester compound or salt thereof, agricultural and horticultural microbicide comprising the compound, and method for using the microbicide

Life of this patent

Abstract

Claims7