Alkynyl pyridine-substituted amide compound and pesticide

Patent metadata

Field	Value
Publication number	US-10029986-B2
Application number	US-201515119660-A
Country	US
Kind code	B2
Filing date	Feb 18, 2015
Priority date	Feb 18, 2014
Publication date	Jul 24, 2018
Grant date	Jul 24, 2018

Abstract

Provided is a novel pesticide, particularly a fungicide and a nematicide. An alkynyl pyridine-substituted amide compound represented by formula (I), its N-oxide or a salt thereof, and a pesticide containing it. [In the formula, G 1 is a structure represented by G 1 -1a, G 1 -3a, G 1 -27a, etc.; X 1 is a halogen atom, difluoromethyl, trifluoromethyl, etc.; Y 1 is a halogen atom, etc.; Y 2 , Y 3 , R 4 and R 5 independently represent a hydrogen atom, etc.; R 1 is a hydrogen atom, a halogen atom, methyl, methoxy, etc.; R 2 is a hydrogen atom, a halogen atom, etc., or R 1 and R 2 together form an alkylene chain thereby to form a cyclopropyl group together with the carbon atom to which R 1 and R 2 are bonded, or R 1 and R 2 together form C 1 -C 2 alkylidene or C 1 -C 2 haloalkylidene; R 3 is a hydrogen atom, methyl, etc.; and R 6 is C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy(C 1 -C 4 )alkyl, etc.]

First claim

The invention claimed is:

1. An alkynyl pyridine-substituted amide compound of the formula (I), its N-oxide or a salt thereof:

wherein:
X 1 is difluoromethyl,
X 2 is a hydrogen atom,
R 7 is methyl,
Y 1 is a hydrogen atom, a halogen atom, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or C 1 -C 4 alkylthio,
Y 2 and Y 3 are each independently a hydrogen atom, a halogen atom or methyl,
R 1 and R 2 are each independently a hydrogen atom, a halogen atom, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl, phenylmethyl, phenylmethyl substituted by (Z) m , C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, cyano(C 1 -C 4 )alkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 haloalkenyloxy, C 3 -C 6 alkynyloxy, C 3 -C 6 haloalkynyloxy, phenyl(C 1 -C 4 )alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkoxyamino, C 1 -C 4 alkoxycarbonyl, —C(O)NH 2 , or —C(S)NH 2 ,
alternatively, R 1 and R 2 together form a C 2 -C 5 alkylene chain thereby to form a 3-6 membered ring together with the carbon atom to which R 1 and R 2 are bonded, wherein the alkylene chain optionally contains one or two oxygen atoms, sulfur atoms or nitrogen atoms and is optionally substituted by a C 1 -C 3 alkyl group, a C 1 -C 3 haloalkyl group or an oxo group, or R 1 and R 2 together form C 1 -C 6 alkylidene, C 1 -C 6 haloalkylidene or C 1 -C 4 alkoxy(C 1 -C 2 )alkylidene,
R 3 and R 4 are each independently a hydrogen atom, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxymethyl, C 3 -C 6 cycloalkyl or phenyl,
alternatively, R 3 and R 4 together form an ethylene chain thereby to form a cyclopropyl ring together with the carbon atom to which R 3 and R 4 are bonded,
further alternatively, R 1 or R 2 , and R 3 or R 4 , together form a C 1 -C 4 alkylene chain thereby to form a 3-6 membered ring together with the carbon atoms to which R 1 or R 2 , and R 3 or R 4 , are bonded, wherein the alkylene chain optionally contains one oxygen atom or sulfur atom,
R 5 is a hydrogen atom, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, (C 1 -C 2 ) alkyl substituted by R 8 , C 3 -C 6 cycloalkyl, C 2 -C 4 alkenyl, C 3 -C 4 alkynyl, —OH, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkylthio, —C(O)R 9 or C 1 -C 4 alkoxycarbonyl,
R 6 is phenyl or phenyl substituted by (Z),
Z is halogen,
m is an integer of 1 to 5,
R 8 is cyano, —OR 14 , C 1 -C 4 alkylthio, C 1 -C 4 alkoxycarbonyl, —C(O)NH 2 , or —C(S)NH 2 ,
R 9 is C 1 -C 4 alkyl, C 1 -C 4 alkoxymethyl, C 3 -C 4 cycloalkyl or C 2 -C 4 alkenyl, and
R 14 is C 1 -C 4 alkyl, C 2 -C 4 haloalkyl, C 1 -C 4 alkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl or C 1 -C 4 alkoxycarbonyl.

2. The compound of claim 1 , wherein:
R 1 and R 2 are H,
R 3 is CH 3 ,
R 4 is H,
R 5 is H,
Y 1 is Cl, and
Y 2 and Y 3 are H.

3. The compound of claim 2 , wherein R 6 is phenyl.

4. A pesticidal composition comprising the alkynyl pyridine-substituted amide compound, its N-oxide or a salt thereof according to claim 1 , as an active ingredient.

5. An agricultural fungicidal or nematicidal composition comprising the alkynyl pyridine-substituted amide compound, its N-oxide or a salt thereof of claim 1 , as an active ingredient.

6. A method comprising applying the agricultural fungicidal or nematicidal composition of claim 5 to a plant by foliar treatment.

7. A method comprising applying the agricultural fungicidal or nematicidal composition of claim 5 to soil in which one or more plants grow.

8. A method comprising applying the agricultural fungicidal or nematicidal composition of claim 5 to a seed, a tuberous root or a rhizome of a plant.

9. An antifungal or endoparasiticidal composition suitable for mammals or birds, comprising the alkynyl pyridine-substituted amide compound, its N-oxide or a salt thereof of claim 1 , as an active ingredient.

10. A method, comprising orally administering the antifungal or endoparasiticidal composition of claim 9 a mammal or a bird.

11. A method, comprising parenterally administering the antifungal or endoparasiticidal composition of claim 9 to a mammal or a bird.

12. The method of claim 11 , wherein the parenteral administration is transdermal administration.

Assignees

• Nissan Chemical Ind Ltd

Inventors

• Mita Takeshi
• Iwasa Motoyoshi
• Nanjo Yusuke
• Shimomiya Taichi
• Kuwahara Hidehito
• Imanaka Hotaka

Classifications

• A61P33/00

  Antiparasitic agents · CPC title

• A61P31/10

  Antimycotics · CPC title

• C07D409/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D417/12

  linked by a chain containing hetero atoms as chain links · CPC title

• A01N43/60

  1,4-Diazines; Hydrogenated 1,4-diazines · CPC title