# 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

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- Number: US 10,306,885 B2
- Document ID: US10306885B2
- Status: Granted
- Kind: B2
- Application number: 15/572,107
- Filed: 2016-05-12
- Published: 2018-05-17
- Granted: 2019-06-04
- Earliest claimed: 2015-05-13
- Assignees: Nihon Nohyaku Co., Ltd.
- Applicants: Nihon Nohyaku Co., Ltd.
- Inventors: Takashi Furuya; Atsushi Okada; Hiroto Harayama; Yutaka Abe; Naoto Shimizu; Eiji Yasukouchi; Yutaka Kato
- Web page: https://patentgrep.com/patent/US10306885B2

## CPC

- A01N 37/46: N-acyl derivatives
- A01N 41/10: Sulfones; Sulfoxides
- A01N 43/40: six-membered rings
- A01N 47/02: the carbon atom having no bond to a nitrogen atom
- C07C 317/44: having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- C07C 317/46: the carbon skeleton being further substituted by singly-bound oxygen atoms
- C07C 321/28: Sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
- C07C 321/30: Sulfides having the sulfur atom of at least one thio group bound to two carbon atoms of six-membered aromatic rings
- C07C 323/62: having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07D 213/81: Amides; Imides
- C07D 213/82: in position 3
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## 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.

## Claims

### Claim 1

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.

### Claim 2 (depends on 1)

The anthranilic acid ester compound or the salt thereof according to claim 1, wherein:
R1 represents:
(a1) a (C1-C6) alkyl group;
(a2) a (C2-C6) alkenyl 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;
(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;
(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;
(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;
(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;
(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; 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;
(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), and
Z represents:
(e1) a (C1-C6) alkyl group;
(e2) a (C2-C6) alkenyl group;
(e3) a (C3-C6) alkynyl group;
(e6) a phenyl (C1-C6) alkyl group; or
(e7) a cyano (C1-C6) alkyl group.

### Claim 3 (depends on 1)

The anthranilic acid ester compound or the salt thereof according to claim 1, wherein:
R3 represents:
(b1) a hydrogen atom;
(b2) a (C1-C6) alkyl group;
(b3) a (C2-C6) alkenyl group;
(b4) a (C2-C6) alkynyl 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; or
(b14) a (C1-C6) alkoxycarbonyl (C1-C6) alkyl group,
R4, R5, R6 and R7 may be the same or different, and each represent:
(c1) a hydrogen atom;
(c2) a halogen atom;
(c6) a halo (C1-C6) alkyl group;
(c10) a halo (C1-C6) alkoxy 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;
(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;
(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;
(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; 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, and
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;
(d5) a halo (C1-C6) alkyl group;
(d6) a halo (C1-C6) alkoxy group;
(d13) a cyclo (C3-C6) alkyl group;
(d14) a phenyl group; or
(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).

### Claim 4 (depends on 1)

A method of making an agricultural or horticultural microbicide comprising mixing the anthranilic acid ester compound or the salt thereof as set forth in claim 1 with water.

### Claim 5 (depends on 1)

A method for treating plants or soil with an agricultural or horticultural microbicide comprising applying an agricultural or horticultural microbicide that comprises the anthranilic acid ester compound or the salt thereof as set forth in claim 1 to a plant or soil.

### Claim 6 (depends on 1)

A method for controlling an agricultural or horticultural disease, the method comprising applying an effective amount of an agricultural or horticultural microbicide comprising the anthranilic acid ester compound or the salt thereof as set forth in claim 1 to a plant or soil prior to or after onset of said agricultural or horticultural disease.

### Claim 7 (depends on 6)

The method according to claim 6, wherein the agricultural or horticultural disease is powdery mildew.