Pyrimidine compound

Patent metadata

Field	Value
Publication number	US-2018317485-A1
Application number	US-201615772314-A
Country	US
Kind code	A1
Filing date	Oct 26, 2016
Priority date	Nov 2, 2015
Publication date	Nov 8, 2018
Grant date	—

Abstract

Provided is a compound represented by formula (I), or an N-oxide thereof:

wherein: A 1 represents a nitrogen atom or a CR 4 ; R 4 represents a hydrogen atom or the like; R 1 represents a C2-C10 chain hydrocarbon group having one or more halogen atoms or the like; R 2 represents a C1-C6 alkyl group optionally having one or more halogen atoms or the like; q represents 0, 1, 2, or 3; R 3 represents a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group B or the like; p represents 0, 1, or 2; R 6 represents a C1-C6 alkyl group optionally having one or more halogen atoms or the like; and n represents 0, 1, or 2. The compound of formula (I) has excellent control efficacies against harmful arthropods.

First claim

1 . A compound represented by formula (I) or an N-oxide thereof:

wherein:
A 1 represents a nitrogen atom or a CR 4 ;
R 4 represents a hydrogen atom, a OR 27 , a NR 27 R 28 , a cyano group, a nitro group, or a halogen atom;
R 1 represents a C2-C10 chain hydrocarbon group having one or more halogen atoms, a (C1-C5 alkoxy)C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfanyl)C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfinyl)C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfonyl)C2-C5 alkyl group having one or more halogen atoms, a (C3-C7 cycloalkyl)C1-C3 alkyl group having one or more substituents selected from Group G, or a C3-C7 cycloalkyl group having one or more substituents selected from Group G;
R 2 represents a C1-C6 alkyl group optionally having one or more halogen atoms, a cyclopropylmethyl group, or a cyclopropyl group;
q represents 0, 1, 2, or 3
wherein when q represents 1, 2, or 3, R 3 represents a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group B, a phenyl group optionally having one or more substituents selected from Group D, a 5 or 6 membered aromatic heterocyclic group optionally having one or more substituents selected from Group D, a OR 12 , a NR 11 R 12 , a NR 11a R 12a , a NR 29 NR 11 R 12 , a NR 24 OR 11 , a NR 11 C(O)R 13 , a NR 29 NR 11 C(O)R 13 , a NR 11 C(O)OR 14 , a NR 29 NR 11 C(O)OR 14 , a NR 11 C(O)NR 15 R 16 , a NR 24 NR 11 C(O)NR 15 R 16 , a N═CHNR 15 R 16 , a N═S(O) x R 15 R 16 , a S(O) y R 15 , a C(O)OR 17 , a C(O)NR 11 R 12 , a cyano group, a nitro group, or a halogen atom, and
wherein when q represents 2 or 3, two or three R 3 may be identical to or different from each other;
p represents 0, 1, or 2
wherein when p represents 1 or 2, R 6 represents a C1-C6 alkyl group optionally having one or more halogen atoms, a OR 3 , a NR 18 R 19 , a cyano group, a nitro group, or a halogen atom, and
wherein when p represents 2, two R 6 may be identical to or different from each other;
R 11 , R 17 , R 18 , R 19 , R 24 , and R 29 represent each independently a hydrogen atom or a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;
R 12 represents a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkyl group having one substituent selected from Group F, or a S(O) 2 R 23 ;
R 23 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms or a phenyl group optionally having one or more substituents selected from Group D;
R 11a and R 12a are combined with the nitrogen atom to which they are attached to represent a 3-7 membered nonaromatic heterocyclic group optionally having one or more substituents selected from Group E, wherein the 3-7 membered nonaromatic heterocyclic group represents an aziridine ring, an azetidine ring, a pyrrolidine ring, an imidazoline ring, an imidazolidine ring, a piperidine ring, a tetrahydropyrimidine ring, a hexahydropyrimidine ring, a piperazine ring, an azepane ring, an oxazolidine ring, an isoxazolidine ring, a 1,3-oxazinane ring, a morpholine ring, a 1,4-oxazepane ring, a thiazolidine ring, an isothiazolidine ring, a 1,3-thiazinane ring, a thiomorpholine ring, or a 1,4-thiazepane ring;
R 13 represents a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group optionally having one or more halogen atoms, a phenyl group optionally having one or more substituents selected from Group D, or a 5 or 6 membered aromatic heterocyclic group optionally having one or more substituents selected from Group D;
R 14 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group optionally having one or more halogen atoms, or a phenyl C1-C3 alkyl group, wherein the phenyl moiety in the phenyl C1-C3 alkyl group may optionally have one or more substituents selected from Group D;
R 15 and R 16 represent each independently a C1-C6 alkyl group optionally having one or more halogen atoms;
R 27 and R 28 represent each independently a hydrogen atom or a C1-C6 alkyl group optionally having one or more halogen atoms;
n and y represent each independently 0, 1, or 2;
x represents 0 or 1;
Group B is selected from the group consisting of a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy 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 C3-C6 cycloalkyl group optionally having one or more halogen atoms, a cyano group, a hydroxy group, and a halogen atom;
Group C is selected from the group consisting of a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy group optionally having one or more halogen atoms, and a halogen atom;
Group D is selected from the group consisting of a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a hydroxy group, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy group optionally having one or more halogen atoms, a sulfanyl group, 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, an amino group, a NHR 21 , a NR 21 R 22 , a C(O)R 21 , a OC(O)R 21 , a C(O)OR 12 , a cyano group, a nitro group, and a halogen atom, wherein R 21 and R 22 represent each independently a C1-C6 alkyl group optionally having one or more halogen atoms;
Group E is selected from the group consisting of a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy group optionally having one or more halogen atoms, a halogen atom, an oxo group, a hydroxy group, a cyano group, and a nitro group;
Group F is selected from the group consisting of a C1-C6 alkoxy group optionally having one or more halogen atoms, an amino group, a NHR 21 , a NR 21 R 22 , a cyano group, a phenyl group optionally having one or more substituents selected from Group D, a 5 or 6 membered aromatic heterocyclic group optionally having one or more substituents selected from Group D, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, and a 3-7 membered nonaromatic heterocyclic group optionally having one or more substituents selected from Group C;
Group G is selected from the group consisting of a halogen atom and a C1-C6 haloalkyl group.

2 . The compound according to claim 1 , wherein
R 4 represents a hydrogen atom or a halogen atom; and R 3 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a phenyl group optionally having one or more substituents selected from Group

Assignees

• Sumitomo Chemical Co

Inventors

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

Classifications

• A61P33/10

  Anthelmintics · CPC title

• A61P33/14

  Ectoparasiticides, e.g. scabicides · CPC title

• C07D239/34

  One oxygen atom · CPC title

• C07D401/04

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

• C07D471/14

  Ortho-condensed systems · CPC title