Alkyl phenyl sulfide derivative and pest control agent

Patent metadata

Field	Value
Publication number	US-10023532-B2
Application number	US-201615091125-A
Country	US
Kind code	B2
Filing date	Apr 5, 2016
Priority date	Apr 20, 2012
Publication date	Jul 17, 2018
Grant date	Jul 17, 2018

Abstract

An alkyl phenyl sulfide derivative represented by the general formula [I] or an agriculturally acceptable salt thereof, and a pest control agent containing the derivative or the salt as an active ingredient.

[in the above formula, R 1 is, for example, a C 1 ˜C 6 alkyl group which is mono- or poly-substituted with halogen atom; R 2 is, for example, a halogen atom or a C 1 ˜C 6 alkyl group; R 3 is, for example, a hydrogen atom or a halogen atom; and R 4 is, for example, a hydrogen atom or a C 1 ˜C 12 alkyl group.] The derivative or the salt has an excellent pest control effect.

First claim

The invention claimed is:

1. An alkyl phenyl sulfide derivative represented by the general formula [I′] or an agriculturally acceptable salt thereof

wherein n is an integer of 0, 1 or 2,
R 1′ is a C 1 -C 6 haloalkyl group (the group excludes 2-bromoethyl group and 3-bromopropyl group), a C 2 -C 8 alkenyl group (the group excludes allyl group), a C 2 -C 8 haloalkenyl group, a C 2 -C 6 alkynyl group, a C 2 -C 6 haloalkynyl group, a branched C 4 -C 6 alkyl group (the group excludes isobutyl group), a C 3 -C 6 cycloalkyl C 1 -C 6 alkyl group or a C 3 -C 6 halocycloalkyl C 1 -C 6 alkyl group,
R 2′ is a halogen atom, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 halocycloalkyl group, a C 1 -C 6 haloalkoxy group, a cyano group or a nitro group,
R 3′ is a hydrogen atom, a halogen atom, a C 1 -C 6 alkyl group or a C 1 -C 6 haloalkyl group.

2. The alkyl phenyl sulfide derivative or an agriculturally acceptable salt thereof, according to claim 1 , wherein R 2 in the general formula [I] is a halogen atom, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group or a cyano group.

3. The alkyl phenyl sulfide derivative or an agriculturally acceptable salt thereof, according to claim 1 , wherein R 3′ in the general formula [I′] is a hydrogen atom, a halogen atom or a C 1 -C 6 alkyl group.

4. An alkyl phenyl sulfide derivative or an agriculturally acceptable salt thereof, according to claim 2 , wherein R 3′ in the general formula [I] is a hydrogen atom, a halogen atom or a C 1 -C 6 alkyl group.

5. A pest control agent comprising an alkyl phenyl sulfide derivative or an agriculturally acceptable salt thereof, according to claim 3 , as an active ingredient; and at least one additive component.

6. A pest control agent comprising:
an alkyl phenyl sulfide derivative or an agriculturally acceptable salt thereof as an active ingredient,
wherein the alkyl phenyl sulfide derivative is represented by the general formula [I′] or the agriculturally acceptable salt thereof

wherein n is an integer of 0, 1 or 2,
R 1′ is a C 1 -C 6 haloalkyl group (the group excludes 2-bromoethyl group), a C 2 -C 8 alkenyl group (the group excludes allyl group), a C 2 -C 8 haloalkenyl group, a C 2 -C 6 alkynyl group, a C 2 -C 6 haloalkynyl group, a branched C 4 -C 6 alkyl group (the group excludes isobutyl group), a C 3 -C 6 cycloalkyl C 1 -C 6 alkyl group or a C 3 -C 6 halocycloalkyl C 1 -C 6 alkyl group,
R 2′ is a halogen atom, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 halocycloalkyl group, a C 1 -C 6 haloalkoxy group, a cyano group or a nitro group,
R 3′ is a hydrogen atom, a halogen atom, a C 1 -C 6 alkyl group or a C 1 -C 6 haloalkyl group.

7. An alkyl phenyl sulfide derivative represented by the general formula [I′] or an agriculturally acceptable salt thereof

wherein n is an integer of 0, 1 or 2,
wherein R 1′ in the general formula [I′] is a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 3,3,3-trifluoropropyl group, a pentafluoroethyl group, a 1,2,2,2-tetrafluoroethyl group, a 2-chloro-2,2-difluoroethyl group, a 2,2,3,3-tetrafluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a 3,3-dichloroallyl group, a propargyl group, a cyclopropylmethyl group or a (2,2-difluorocyclopropyl)methyl group,
wherein R 2′ is a halogen atom, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 halocycloalkyl group, a C 1 -C 6 haloalkoxy group, a cyano group or a nitro group, and
wherein R 3′ is a hydrogen atom, a halogen atom, a C 1 -C 6 alkyl group or a C 1 -C 6 haloalkyl group.

8. The alkyl phenyl sulfide derivative or an agriculturally acceptable salt thereof, according to claim 7 , wherein R 2′ in the general formula [I′] is a halogen atom, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group or a cyano group.

9. The alkyl phenyl sulfide derivative or an agriculturally acceptable salt thereof, according to claim 7 , wherein R 3′ in the general formula [I] is a hydrogen atom, a halogen atom or a C 1 -C 6 alkyl group.

10. A pest control agent which contains, as an active ingredient, an alkyl phenyl sulfide derivative or an agriculturally acceptable salt thereof, according to claim 7 .

Assignees

• Kumiai Chemical Industry Co

Inventors

• Domon Kei
• Toriyabe Keiji
• Ogawa Yutaka
• Bessho Junichiro
• Kawamoto Kei
• Watanabe Akira
• Komatsu Masaaki
• Matsuda Takeshi
• Ito Seisuke

Classifications

• C07C317/22

  with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton · CPC title

• C07C317/32

  with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton · CPC title

• C07C323/25

  the carbon skeleton being acyclic and saturated · CPC title

• C07C323/62

  having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton · CPC title

• C07C323/20

  with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring · CPC title