Amide derivatives, process for preparation thereof and use thereof as insecticide

Patent metadata

Field	Value
Publication number	US-2016002198-A1
Application number	US-201514854627-A
Country	US
Kind code	A1
Filing date	Sep 15, 2015
Priority date	Jan 28, 2004
Publication date	Jan 7, 2016
Grant date	—

Abstract

An object of the present invention is to provide a compound represented by Formula (1):

wherein A 1 , A 2 , A 3 and A 4 each represent a carbon atom, a nitrogen atom or an oxidized nitrogen atom;
R 1 and R 2 each represent a hydrogen atom, an optionally substituted alkyl group or an optionally substituted C1-C4 alkylcarbonyl group;
G 1 and G 2 each represent an oxygen atom or a sulfur atom;
X, which may be identical or different each other, represents a hydrogen atom, a halogen atom, a C1-C3 alkyl group or a trifluoromethyl group;
n is an integer of 0 to 4; and
Q 1 represents an optionally substituted phenyl group, an optionally substituted naphthyl group or an optionally substituted heterocyclic group;
Q 2 represents a phenyl group or heterocyclic group having one or more substituents, at least one of the substituent being any of a C1-C4 haloalkoxy group, a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group and a C1-C6 perfluoroalkylsulfonyl group,
an insecticide comprising the compound as the active ingredient, and a process for preparation thereof.

First claim

1 - 14 . (canceled)

15 . A compound represented by Formula (4):

wherein (a) in the case of R 1 represents a hydrogen atom;
A 1 , A 2 , A 3 and A 4 represent a carbon atom;
G 1 and G 2 each represent an oxygen atom or a sulfur atom;
X represents a hydrogen atom;
n represents 4;
Q 1 represents a substituted phenyl group having one or more substituents, which may be identical or different, selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a cyano group and a nitro group; a pyridyl group; or a substituted pyridyl group having one or more substituents, which may be identical or different, selected from a halogen atom;
(b) in the case of R 1 represents a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group;
A 1 , A 2 , A 3 and A 4 each represent a carbon atom, a nitrogen atom or an oxidized nitrogen atom;
G 1 and G 2 each represent an oxygen atom or a sulfur atom;
X, which may be identical or different each other, represents a hydrogen atom, a halogen atom, an optionally substituted C1-C3 alkyl group or a trifluoromethyl group;
n represents an integer of 0 to 4;
Q 1 represents a phenyl group; a substituted phenyl group having one or more substituents, which may be identical or different, selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a C1-C4 alkylamino group, a di-C1-C4-alkylamino group, a cyano group, a nitro group, a hydroxyl group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group; a heterocyclic group (the heterocyclic group herein represents a pyridyl group, a pyridin-N-oxide group, a pyrimidinyl group, a pyridazyl group, a pyrazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, an imidazolyl group, a triazolyl group, a pyrrolyl group, a pyrazolyl group or a tetrazolyl group); or a substituted heterocyclic group (which means the same as those described above) having one or more substituents, which may be identical or different, selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a C1-C4 alkylamino group, a di-C1-C4-alkylamino group, a cyano group, a nitro group, a hydroxyl group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group or a phenyl group; and
Hal represents a chlorine atom or a bromine atom; and
excluding the following compounds;

16 . A compound represented by Formula (6):

wherein A 1 , A 2 , A 3 and A 4 each represented by a carbon atom, a nitrogen atom or an oxidized nitrogen atom;
R 1 and R 2 each represent a hydrogen atom, a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group;
G 2 represents an oxygen atom or a sulfur atom;
X, which may be identical or different, represents a hydrogen atom, a halogen atom, an optionally substituted C1-C3 alkyl group or a trifluoromethyl group;
n represents an integer of 0 to 4;
Q 2 is represented either by Formula (2):

(wherein Y 1 and Y 5 , which may be identical or different, each represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y 3 represents a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y 2 and Y 4 each represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group);
or by Formula (3):

(wherein Y 6 and Y 9 , which may be identical or different, each represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y 8 represents a C1-C4 haloalkoxy group, a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y 7 represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group).

17 . A compound represented by Formula (8):

wherein X 1 a, X 2 a, X 3 a and X 4 a each represent a hydrogen atom, a C1-C3 alkyl group, a trifluoromethyl group, a hydroxyl group, an amino group or a halogen atom;
R a and R b each represent a fluorine atom or a C1-C4 perfluoroalkyl group;
R c represents a hydroxyl group, a group —O—R d (wherein R d represents a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkylsulfonyl, a C1-C3 haloalkylsulfonyl group, an arylsulfonyl group, a C1-C4 alkylcarbonyl group or a C1-C4 haloalkylcarbonyl group), a chlorine atom, a bromine atom or an iodine atom;
R 2 a represents a hydrogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C4 alkylthio group, a C1-C4 haloalkylthio group, a C1-C4 alkylcarbonyl group or a C1-C4 haloalkylcarbonyl group;
Y 1 a and Y 5 a each represent a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkylthio group, a C1-C4 haloalkylthio group, a C1-C3 alkylsulfinyl group or a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a cyano group, a hydroxyl group or a halogen atom;
Y 2 a and Y 4 a each represent a hydrogen atom, a C1-C4 alkyl group or a halogen atom; and
G 2 a represents an oxygen atom or a sulfur atom.

18 . A compound represented by Formula (11):

wherein X 1 a, X 2 a, X 3 a and X 4 a each represent a hydrogen atom, a C1-C3 alkyl group, a trifluoromethyl group, a hydroxyl group, an amino group or a halogen atom;
R a and R b each represent a fluorine atom or a C1-C4 perfluoroalkyl group;
R c represents a hydroxyl group, a group —O—R d (wherein R d represents a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an arylsulfonyl group, a C1-C4 alkylcarbonyl group or a C1-C4 haloalkylcarbonyl group),

Assignees

• Mitsui Chemicals Inc

Inventors

• Yoshida Kei
• Wakita Takeo
• Katsuta Hiroyuki
• Kai Akiyoshi
• Chiba Yutaka
• Takahashi Kiyoshi
• Kato Hiroko
• Kawahara Nobuyuki
• Nomura Michikazu
• Daido Hidenori
• Maki Junji
• Banba Shinichi

Classifications

• C07D213/64

  attached in position 2 or 6 · CPC title

• C07D309/28

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms · CPC title

• C07C317/40

  Y being a hydrogen or a carbon atom · CPC title

• A01N43/40

  six-membered rings · CPC title

• C07D241/24

  Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals · CPC title