Pyridazine compound

Patent metadata

Field	Value
Publication number	US-9924719-B2
Application number	US-201515515879-A
Country	US
Kind code	B2
Filing date	Sep 29, 2015
Priority date	Oct 3, 2014
Publication date	Mar 27, 2018
Grant date	Mar 27, 2018

Abstract

A pyridazine compound represented by formula (1):

wherein A represents a nitrogen atom or a CR 6 , R 1 represents a C2-C10 alkyl group having one or more halogen atoms, etc., R 2 and R 3 represent independently of each other a hydrogen atom, etc., R 4 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, R 5 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, etc., R 6 represents a hydrogen atom, etc., n represents 0, 1, or 2, and p represents 0, 1, or 2, has an excellent efficacy for controlling harmful arthropods.

First claim

The invention claimed is:

1. A pyridazine compound represented by formula (1):

wherein,
A represents a nitrogen atom or a CR 6 ;
R 1 represents a C2-C10 alkyl group, a C3-C10 alkenyl group, a C3-C10 alkynyl group, a (C1-C5 alkyl)-O—(C2-C5 alkyl) group, a (C3-C5 alkenyl)-O—(C2-C5 alkyl) group, a (C3-C5 alkynyl)-O—(C2-C5 alkyl) group, a (C1-C5 alkyl)-S(O) m —(C2-C5 alkyl) group, a (C3-C5 alkenyl)-S(O) m —(C2-C5 alkyl) group, a (C3-C5 alkynyl)-S(O) m —(C2-C5 alkyl) group, or a (C1-C5 alkyl)-C(O)—(C1-C5 alkyl) group, wherein R 1 has one or more halogen atoms;
R 2 and R 3 represent independently of each other a hydrogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, a C2-C6 alkoxycarbonyl group, a cyano group, or a halogen atom;
R 4 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;
R 5 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a phenyl group optionally having one or more atoms or groups selected from Group A, a 5-membered aromatic heterocyclic group selected from Group B, wherein said 5-membered aromatic heterocyclic group may optionally have one or more atoms or groups selected from Group A, a 6-membered aromatic heterocyclic group selected from Group C, wherein said 6-membered aromatic heterocyclic group may optionally have one or more atoms or groups selected from Group A, a 3 to 7 membered nonaromatic heterocyclic group selected from Group D, wherein the 3 to 7 membered nonaromatic heterocyclic group may optionally have one or more atoms or groups selected from the group consisting of a halogen atom and a C1-C6 alkyl group, a OR 7 , a NR 8 R 9 , a NR 8 C(O)R 10 , a NR 8 C(O)OR 11 , a NR 8 C(O)NR 12 R 13 , a N═CHNR 12 R 13 , a N═S(O)R 12 R 13 , a S(O) y R 12 , a C(O)OR 8 , a cyano group, or a halogen atom;
R 6 represents a hydrogen atom, or a halogen atom;
R 7 represents a hydrogen atom, a C1-C6 alkyl group, a C3-C6 alkenyl group, a C3-C6 alkynyl group, a (C1-C3 alkyl)-O—(C1-C3 alkyl) group, a (C1-C3 alkyl)-S(O) y —(C1-C3 alkyl) group, a C3-C7 cycloalkyl group, a (C3-C7 cycloalkyl)-(C1-C3 alkyl) group, wherein said C1-C6 alkyl group, said C3-C6 alkenyl group, said C3-C6 alkynyl group, said (C1-C3 alkyl)-O—(C1-C3 alkyl) group, said (C1-C3 alkyl)-S(O) y —(C1-C3 alkyl) group, said C3-C7 cycloalkyl group, and said (C3-C7 cycloalkyl)-(C1-C3 alkyl) group may optionally have one or more halogen atoms, or a phenyl C1-C3 alkyl group, wherein the phenyl moiety in said phenyl C1-C3 alkyl group may optionally have one or more atoms or groups selected from Group A;
R 8 represents a hydrogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, a C3-C6 alkenyl group optionally having one or more halogen atoms, or a C3-C6 alkynyl group optionally having one or more halogen atoms;
R 9 represents a hydrogen atom, a C1-C6 alkyl group, a C3-C6 alkenyl group, a C3-C6 alkynyl group, a (C1-C3 alkyl)-O—(C1-C3 alkyl) group, a (C1-C3 alkyl)-S(O) y —(C1-C3 alkyl) group, a C3-C7 cycloalkyl group, a (C3-C7 cycloalkyl)-(C1-C3 alkyl) group, wherein said C1-C6 alkyl group, said C3-C6 alkenyl group, said C3-C6 alkynyl group, said (C1-C3 alkyl)-O—(C1-C3 alkyl) group, said (C1-C3 alkyl)-S(O) y —(C1-C3 alkyl) group, said C3-C7 cycloalkyl group, and said (C3-C7 cycloalkyl)-(C1-C3 alkyl) group may optionally have one or more halogen atoms,
a cyano C1-C6 alkyl group,
a phenyl C1-C3 alkyl group, wherein the phenyl moiety in said phenyl C1-C3 alkyl group may optionally have one or more atoms or groups selected from Group A, or
a (5 or 6 membered heteroaryl)C1-C3 alkyl group, wherein the 5 or 6 membered heteroaryl moiety in said (5 or 6 membered heteroaryl)C1-C3 alkyl group may optionally have one or more atoms or groups selected from Group A;
R 10 represents a hydrogen atom, a C1-C6 alkyl group, a C3-C6 alkenyl group, a C3-C6 alkynyl group, a C3-C7 cycloalkyl group, a (C3-C7 cycloalkyl)-(C1-C3 alkyl) group, wherein said C1-C6 alkyl group, said C3-C6 alkenyl group, said C3-C6 alkynyl group, said C3-C7 cycloalkyl group, and said (C3-C7 cycloalkyl)-(C1-C3 alkyl) group may optionally have one or more halogen atoms, or a phenyl C1-C3 alkyl group, wherein the phenyl moiety in said phenyl C1-C3 alkyl group may optionally have one or more atoms or substituents selected from Group A;
R 11 represents a C1-C6 alkyl group optionally having one or more halogen atoms, a C3-C6 alkenyl group optionally having one or more halogen atoms, a C3-C6 alkynyl group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, a (C3-C7 cycloalkyl)-(C1-C3 alkyl) group optionally having one or more halogen atoms, wherein said (C3-C7 cycloalkyl)-(C1-C3 alkyl) group may optionally have one or more halogen atoms, or a phenyl C1-C3 alkyl group, wherein the phenyl moiety in said phenyl C1-C3 alkyl group may optionally have one or more atoms or groups selected from Group A;
R 12 and R 13 represent independently of each other a C1-C6 alkyl group optionally having one or more halogen atoms;
R 14 represents a hydrogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally having one or more halogen atoms, or a C2-C6 alkoxycarbonyl group optionally having one or more halogen atoms;
n represents 0, 1, or 2;
m represents 0, 1, or 2;
p represents 0, 1, 2, or 3, wherein when p represents 2 or 3, a plurality of R 5 may be identical or different;
x represents 0 or 1;
y represents 0, 1, or 2;
Group A: a group consisting of a C1-C6 alkyl group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, a cyano group, and a halogen atom;

2. The compound according to claim 1 , wherein A represents CR 6 .

3. The compound according to claim 1 , wherein A represents a nitrogen atom.

4. The compound according to claim 1 , wherein R 4 represents a C1-C6 alkyl group optionally having one or more halogen atoms.

5. The compound according to claim 1 , wherein R 4 represents an ethyl group.

6. The compound according to claim 1 , wherein
R 1 represents a C2-C10 haloalkyl group;
R 2 and R 3 represent independently of each other a hydrogen atom, a C1-C3 alkyl group optionally having one or more halogen atoms, or a halogen atom;
R 4 represents a C1-C6 alkyl group optionally having one or more halogen atoms;
R 5 represents a C1-C6 alkyl group optionally having one or more halogen atoms; and
p represents 0 or 1.

7. The compound according to claim 1 , wherein
R 1 represents a C2-C10 haloalkyl group;
R 2 and R 3 represent each a hydrogen atom;
R 4 represents a C1-C6 alkyl group optionally having one or more halogen atoms;
R 5 represents a C1-C6 alkyl group optionally having one or more halogen atoms; and
p represents 0 or 1.

8. The compound according to claim 1 , wherein
R 1 represents a C3-C6 alkyl having four or more fluorine atoms;
R 2 and R 3 represent each a hydrogen atom;
R 4 represents an ethyl group;
R 5 represents a C1-C6 alkyl group optionally having one or more halogen atoms; and
p represents 0 or 1.

9. A compound represented by formula (1-N):

Assignees

• Sumitomo Chemical Co

Inventors

• Tanabe Takamasa
• Nokura Yoshihiko
• Maehata Ryota
• Orimoto Kohei
• Nakajima Yuji

Classifications

• C07D237/14

  Oxygen atoms · CPC title

• A01N43/58 Primary

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

• C07D401/04 Primary

  directly linked by a ring-member-to-ring-member bond · CPC title