Amide compound or salt thereof, agricultural and horticultural insecticide and microbicide comprising the compound, and method for using the insecticide and microbicide

Patent metadata

Field	Value
Publication number	US-10123537-B2
Application number	US-201715668999-A
Country	US
Kind code	B2
Filing date	Aug 4, 2017
Priority date	Nov 12, 2013
Publication date	Nov 13, 2018
Grant date	Nov 13, 2018

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 amide compound represented by the general formula (I):

(wherein A 1 , A 2 and A 3 each represent a nitrogen atom or a CH group, R 1 represents an alkyl group, R 2 and R 4 each represent a haloalkyl group, R 3 represents an alkyl group, and m represents 0, 1 or 2) or a salt thereof; an agricultural and horticultural insecticide and microbicide comprising the compound or a salt thereof as an active ingredient; and a method for using the insecticide and microbicide.

First claim

The invention claimed is:

1. A method for controlling an agricultural and horticultural fungal disease, comprising applying, to plants or soil, an effective amount of an amide compound represented by the formula:

wherein
R 1 represents

(a1) a (C 1 -C 6 ) alkyl group;
(a2) a (C 2 -C 6 ) alkenyl group;
(a3) a (C 2 -C 6 ) alkynyl group;
(a4) a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group;
(a6) a halo (C 2 -C 6 ) alkenyl group;
(a7) a halo (C 2 -C 6 ) alkynyl group; or
(a8) a halo (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group,
R 2 and R 4 may be the same or different, and each represent

(b1) a halogen atom;
(b2) a cyano group;
(b3) a nitro group;
(b4) a (C 1 -C 6 ) alkyl group;
(b5) a halo (C 1 -C 6 ) alkyl group;
(b6) a (C 3 -C 6 ) cycloalkyl group;
(b7) a halo (C 3 -C 6 ) cycloalkyl group;
(b8) a (C 1 -C 6 ) alkoxy group;
(b9) a halo (C 1 -C 6 ) alkoxy group;
(b10) a (C 1 -C 6 ) alkylthio group;
(b11) a (C 1 -C 6 ) alkylsulfinyl group;
(b12) a (C 1 -C 6 ) alkylsulfonyl group;
(b13) a halo (C 1 -C 6 ) alkylthio group;
(b14) a halo (C 1 -C 6 ) alkylsulfinyl group;
(b15) a halo (C 1 -C 6 ) alkylsulfonyl group;
(b16) a (C 1 -C 6 ) alkoxy halo (C 1 -C 6 ) alkyl group;
(b17) a pentafluorothio group;
(b18) a tri-(C 1 -C 6 ) alkylsilyl group, wherein the alkyl groups of the tri-(C 1 -C 6 ) alkyl moiety may be the same or different; or
(b19) a hydrogen atom,
R 3 represents

(c1) a hydrogen atom;
(c2) a (C 1 -C 6 ) alkyl group;
(c3) a (C 3 -C 6 ) cycloalkyl group;
(c4) a (C 1 -C 6 ) alkoxy group;
(c5) a halo (C 1 -C 6 ) alkyl group;
(c6) a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group;
(c7) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group;
(c8) a (C 1 -C 6 ) alkoxycarbonyl group;
(c9) a (C 1 -C 6 ) alkylthio (C 1 -C 6 ) alkyl group;
(c10) a (C 1 -C 6 ) alkylsulfinyl (C 1 -C 6 ) alkyl group;
(c11) a (C 1 -C 6 ) alkylsulfonyl (C 1 -C 6 ) alkyl group;
(c12) a (C 2 -C 6 ) alkenyl group;
(c13) a (C 2 -C 6 ) alkynyl group;
(c14) a cyano (C 1 -C 6 ) alkyl group;
(c15) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group;
(c16) a (C 1 -C 6 ) alkylcarbonyl group; or
(c17) a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) carbonyl group,
m represents 0, 1 or 2,
A 1 , A 2 and A 3 may be the same or different, and each represent a nitrogen atom or a C—R 5 group, wherein R 5 represents

(d1) a hydrogen atom,
R 6 represents

(e1) a hydrogen atom,
R 7 represents

(e3) a cyano group;
(e4) a (C 1 -C 6 ) alkyl group;
(e5) a (C 1 -C 6 ) alkoxy group;
(e6) a (C 1 -C 6 ) alkylthio group;
(e7) a (C 1 -C 6 ) alkylsulfinyl group;
(e8) a (C 1 -C 6 ) alkylsulfonyl group;
(e9) a (C 2 -C 6 ) alkenyl group;
(e10) a (C 2 -C 6 ) alkynyl group;
(e11) a (C 3 -C 6 ) cycloalkyl group; or
(e12) a tri-(C 1 -C 6 ) alkylsilyl (C 2 -C 6 ) alkynyl group, wherein the alkyl groups of the tri-(C 1 -C 6 ) alkyl moiety may be the same or different, and
X is an oxygen atom or a sulfur atom, or

a salt thereof.

2. The method according to claim 1 , wherein
R 1 represents

(a1) a (C 1 -C 6 ) alkyl group,
R 2 and R 4 may be the same or different, and each represent

(b1) a halogen atom;
(b4) a (C 1 -C 6 ) alkyl group;
(b5) a halo (C 1 -C 6 ) alkyl group;
(b8) a (C 1 -C 6 ) alkoxy group;
(b9) a halo (C 1 -C 6 ) alkoxy group;
(b10) a (C 1 -C 6 ) alkylthio group;
(b12) a (C 1 -C 6 ) alkylsulfonyl group;
(b13) a halo (C 1 -C 6 ) alkylthio group;
(b16) a (C 1 -C 6 ) alkoxy halo (C 1 -C 6 ) alkyl group;
(b18) a tri-(C 1 -C 6 ) alkylsilyl group, wherein the alkyl groups of the tri-(C 1 -C 6 ) alkyl moiety may be the same or different; or
(b19) a hydrogen atom,
R 3 represents

(c1) a hydrogen atom;
(c2) a (C 1 -C 6 ) alkyl group;
(c3) a (C 3 -C 6 ) cycloalkyl group;
(c4) a (C 1 -C 6 ) alkoxy group;
(c7) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group;
(c8) a (C 1 -C 6 ) alkoxycarbonyl group;
(c9) a (C 1 -C 6 ) alkylthio (C 1 -C 6 ) alkyl group;
(c10) a (C 1 -C 6 ) alkylsulfinyl (C 1 -C 6 ) alkyl group;
(c12) a (C 2 -C 6 ) alkenyl group;
(c14) a cyano (C 1 -C 6 ) alkyl group; or
(c15) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group,
m represents 0, 1 or 2,
A 1 , A 2 and A 3 may be the same or different, and each represent a nitrogen atom or a C—R 5 group, wherein R 5 represents

(d1) a hydrogen atom,
R 6 represents

(e1) a hydrogen atom,
R 7 represents

(e3) a cyano group;
(e4) a (C 1 -C 6 ) alkyl group;
(e5) a (C 1 -C 6 ) alkoxy group;
(e6) a (C 1 -C 6 ) alkylthio group; or
(e7) a (C 1 -C 6 ) alkylsulfinyl group, and
X is an oxygen atom or a sulfur atom.

3. The method according to claim 1 , wherein
R 1 represents

(a1) a (C 1 -C 6 ) alkyl group,
R 2 and R 4 may be the same or different, and each represent

(b1) a halogen atom;
(b5) a halo (C 1 -C 6 ) alkyl group;
(b8) a (C 1 -C 6 ) alkoxy group;
(b9) a halo (C 1 -C 6 ) alkoxy group;
(b10) a (C 1 -C 6 ) alkylthio group;
(b12) a (C 1 -C 6 ) alkylsulfonyl group;
(b13) a halo (C 1 -C 6 ) alkylthio group;
(b16) a (C 1 -C 6 ) alkoxy halo (C 1 -C 6 ) alkyl group;
(b18) a tri-(C 1 -C 6 ) alkylsilyl group, wherein the alkyl groups of the tri-(C 1 -C 6 ) alkyl moiety may be the same or different; or
(b19) a hydrogen atom,
R 3 represents

(c1) a hydrogen atom;
(c2) a (C 1 -C 6 ) alkyl group;
(c3) a (C 3 -C 6 ) cycloalkyl group;
(c7) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group;
(c8) a (C 1 -C 6 ) alkoxycarbonyl group;
(c9) a (C 1 -C 6 ) alkylthio (C 1 -C 6 ) alkyl group;
(c10) a (C 1 -C 6 ) alkylsulfinyl (C 1 -C 6 ) alkyl group;
(c12) a (C 2 -C 6 ) alkenyl group;
(c14) a cyano (C 1 -C 6 ) alkyl group; or
(c15) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group,
m represents 0, 1 or 2,
A 1 , A 2 and A 3 may be the same or different, and each represent a nitrogen atom or a C—R 5 group, wherein R 5 represents

(d1) a hydrogen atom,
R 6 represents

(e1) a hydrogen atom,
R 7 represents

(e4) a (C 1 -C 6 ) alkyl group;
(e5) a (C 1 -C 6 ) alkoxy group; or
(e6) a (C 1 -C 6 ) alkylthio group, and
X is an oxygen atom or a sulfur atom.

4. The method according to claim 1 , wherein A 2 is a nitrogen atom and A 3 is CH.

5. The method according to claim 2 , wherein A 2 is a nitrogen atom and A 3 is CH.

6. The method according to claim 3 , wherein A 2 is a nitrogen atom and A 3 is CH.

7. The method according to claim 1 , wherein A 2 and A 3 are nitrogen atoms.

8. The method according to claim 2 , wherein A 2 and A 3 are nitrogen atoms.

9. The method according to claim 3 , wherein A 2 and A 3 are nitrogen atoms.

10. The method according to claim 1 , wherein A 2 and A 3 are CH groups.

11. The method according to claim 2 , wherein A 2 and A 3 are CH groups.

Assignees

• Nihon Nohyaku Co Ltd

Inventors

• Yonemura Ikki
• Matsuo Soichiro
• Suwa Akiyuki
• Yamashita Masao
• Okada Atsushi

Classifications

• C07D213/75

  Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates · CPC title

• C07C323/42

  Y being a carbon atom of a six-membered aromatic ring · CPC title

• C07C317/44

  having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton · CPC title

• A01N43/58

  1,2-Diazines; Hydrogenated 1,2-diazines · CPC title

• A01N41/10

  Sulfones; Sulfoxides · CPC title