Alkyl phenyl sulfide derivative and pest control agent

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), 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,

R 4 is a C 1 -C 12 alkyl group (the group may be mono- or poly-substituted with R 5 ), a C 3 -C 6 cycloalkyl group (the group may be mono- or poly-substituted with R 5 ), a C 2 -C 8 alkenyl group (the group may be mono- or poly-substituted with R 5 ), a C 2 -C 6 alkynyl group (the group may be mono- or poly-substituted with R 5 ) or a benzoyl group (the group may be mono- or poly-substituted with R 6 ),

R 5 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 (the group may be mono- or poly-substituted with R 6 ), a C 3 -C 6 halocycloalkyl group, a hydroxyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 haloalkoxy group, a C 3 -C 6 cycloalkoxy group, a C 3 -C 6 halocycloalkoxy group, a C 1 -C 6 alkoxy C 1 -C 6 alkoxy group, a C 1 -C 6 haloalkoxy C 1 -C 6 alkoxy group, a C 1 -C 6 haloalkoxy C 1 -C 6 haloalkoxy group, a C 1 -C 6 alkylsulfinyloxy group, a C 1 -C 6 haloalkylsulfinyloxy group, a C 3 -C 6 cycloalkylsulfinyloxy group, a C 3 -C 6 halocycloalkylsulfinyloxy group, a C 1 -C 6 alkylsulfonyloxy group, a C 1 -C 6 haloalkylsulfonyloxy group, a C 3 -C 6 cycloalkylsulfonyloxy group, a C 3 -C 6 halocycloalkylsulfonyloxy group, a thiol group, a C 1 -C 6 alkylthio group, a C 1 -C 6 haloalkylthio group, a C 2 -C 6 alkenylthio group, a C 2 -C 6 haloalkenylthio group, a C 3 -C 6 cycloalkylthio group, a C 3 -C 6 halocycloalkylthio group, a C 3 -C 6 cycloalkyl C 1 -C 6 alkylthio group, a C 3 -C 6 halocycloalkyl C 1 -C 6 alkylthio group, a tri(C 1 -C 6 alkyl)silyl C 1 -C 6 alkylthio group, a C 1 -C 6 alkylsulfinyl group, a C 1 -C 6 haloalkylsulfinyl group, a C 3 -C 6 cycloalkylsulfinyl group, a C 3 -C 6 halocycloalkylsulfinyl group, a C 1 -C 6 alkylsulfonyl group, a C 1 -C 6 haloalkylsulfonyl group, a C 3 -C 6 cycloalkylsulfonyl group, a C 3 -C 6 halocycloalkylsulfonyl group, a C 1 -C 6 alkylcarbonyl group, a C 1 -C 6 haloalkylcarbonyl group, a formyl group, a C 1 -C 6 alkylcarbonyloxy group, a C 1 -C 6 haloalkylcarbonyloxy group, a formyloxy group, an amino group, a C 1 -C 6 alkylcarbonylamino group (the amino group may be substituted with R 9 ), a C 1 -C 6 haloalkylcarbonylamino group (the amino group may be substituted with R 9 ), a phenylcarbonylamino group (the phenyl group may be mono- or poly-substituted with R 6 , the amino group may be substituted with R 9 ), a C 1 -C 6 alkoxycarbonylamino group (the amino group may be substituted with R 9 ), a C 1 -C 6 haloalkoxycarbonylamino group (the amino group may be substituted with R 9 ), a C 1 -C 6 alkylaminocarbonylamino group (the amino group may be substituted with R 9 ), a C 1 -C 6 haloalkylaminocarbonylamino group (the amino group may be substituted with R 9 ), a C 1 -C 6 alkylsulfonylamino group (the amino group may be substituted with R 9 ), a C 1 -C 6 haloalkylsulfonylamino group (the amino group may be substituted with R 9 ), a phenylsulfonylamino group (the phenyl group may be substituted with R 6 , the amino group may be substituted with R 9 ), a C 1 -C 6 alkylamino group (the amino group may be substituted with R 9 ), a C 1 -C 6 haloalkylamino group (the amino group may be substituted with R 9 ), a C 1 -C 6 alkylaminocarbonylthio group (the amino group may be substituted with R 9 ), a C 1 -C 6 haloalkylaminocarbonylthio group (the amino group may be substituted with R 9 ), a C 1 -C 6 alkylaminocarbonyl group (the amino group may be substituted with R 9 ), a C 1 -C 6 haloalkylaminocarbonyl group (the amino group may be substituted with R 9 ), a C 1 -C 6 alkoxycarbonyl group, a C 1 -C 6 haloalkoxycarbonyl group, a tri(C 1 -C 6 alkyl)silyl group, a phenyl group (the group may be mono- or poly-substituted with R 6 ), a pyridyloxyphenyl group (the pyridyl group may be mono- or poly-substituted with R 6 ), a phenoxy group (the group may be mono- or poly-substituted with R 6 ), a phenyl C 1 -C 6 alkoxy group (the phenyl group may be mono- or poly-substituted with R 6 ), a phenylcarbonyloxy group (the phenyl group may be mono- or poly-substituted with R 6 ), a phenylcarbonyl group (the phenyl group may be mono- or poly-substituted with R 6 ), a benzoyl group (the group may be mono- or poly-substituted with R 6 ), a benzoyloxy group (the group may be mono- or poly-substituted with R 6 ), a phenylthio group (the group may be mono- or poly-substituted with R 6 ), a phenylsulfonyl group (the group may be mono- or poly-substituted with R 6 ), a phenylsulfinyl group (the group may be mono- or poly-substituted with R 6 ), a phenyl C 1 -C 6 alkylthio group (the phenyl group may be mono- or poly-substituted with R 6 ), a phenyl C 1 -C 6 alkylsulfinyl group (the phenyl group may be mono- or poly-substituted with R 6 ), a phenyl C 1 -C 6 alkylsulfonyl group (the phenyl group may be mono- or poly-substituted with R 6 ), a —O—N═C(R 7 )(R 8 ) group, an adamantyl group, a pyrrolyl group (the group may be mono- or poly-substituted with R 6 ), a pyrazolyl group (the group may be mono- or poly-substituted with R 6 ), an imidazolyl group (the group may be mono- or poly-substituted with R 6 ), a triazolyl group (the group may be mono- or poly-substituted with R 6 ), an oxazolyl group (the group may be mono- or poly-substituted with R 6 ), an isoxazolyl group (the group may be mono- or poly-substituted with R 6 ), a thiazolyl group (the group may be mono- or poly-substituted with R 6 ), an isothiazolyl group (the group may be mono- or poly-substituted with R 6 ), a pyridyl group (the group may be mono- or poly-substituted with R 6 and the nitrogen atom of the group may be oxidized to form N-oxide), a pyrimidinyl group (the group may be mono- or poly-substituted with R 6 ), a pyridyloxy group (the group may be mono- or poly-substituted with R 6 ), a tetrahydrofuranyl group (the group may be mono- or poly-substituted with R 6 ), 1,3-dioxoisoindolinyl group (the group may be mono- or poly-substituted with R 6 ), a cyano group, a nitro group, a carboxyl group, a thiocyanato group or an aminoxy group,

R 6 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 3 -C 6 cycloalkyl C 1 -C 6 alkyl group, a C 3 -C 6 halocycloalkyl C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 haloalkoxy group, a C 1 -C 6 alkylthio group, a C 1 -C 6 haloalkylthio group, a C 1 -C 6 alkylsulfinyl group, a C 1 -C 6 haloalkylsulfinyl group, a C 1 -C 6 alkylsulfonyl group, a C 1 -C 6 haloalkylsulfonyl group, a C 1 -C 6 alkylthio C 1 -C 6 alkyl group, a C 1 -C 6 haloalkylthio C 1 -C 6 alkyl group, a C 1 -C 6 alkylsulfonyloxy group, a C 1 -C 6 haloalkylsulfonyloxy group, a phenyl group (the group may be mono- or poly-substituted with halogen atom, alkyl group or haloalkyl group), a phenyl C 1 -C 6 alkyl group, a phenyl C 1 -C 6 alkoxy group, a cyano group or a nitro group,

R 7 and R 8 may be the same or different, are each a hydrogen 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 or a phenyl group (the group may be mono- or poly-substituted with R 6 ), and may form a 3- to 6-membered ring together with the carbon atom to which they bond, and

R 9 is 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 alkylcarbonyl group, a C 1 -C 6 haloalkylcarbonyl group, a C 1 -C 6 alkoxycarbonyl group, a C 1 -C 6 haloalkoxycarbonyl group, a C 1 -C 6 alkylaminocarbonyl group, a C 1 -C 6 haloalkylaminocarbonyl group or benzoyl group (the group may be mono- or poly-substituted with R 6 .

2. An alkyl phenyl sulfide derivative or an agriculturally acceptable salt thereof,

according to claim 1 , 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, 1,2,2,2-tetrafluoroethyl group, 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.

3. An 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.

4. An 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.

5. A pest control agent comprising an alkyl phenyl sulfide derivative or an agriculturally acceptable salt thereof, according to claim 1 , as an active ingredient; and at least one additive component.

6. An alkyl phenyl sulfide derivative or an agriculturally acceptable salt thereof, according to claim 2 , 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.

7. 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.

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

9. A pest control agent which contains, as an active ingredient, an alkyl phenyl sulfide derivative or an agriculturally acceptable salt thereof, according to claim 2 .

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 3 .

11. A pest control agent comprising an alkyl phenyl sulfide derivative or an agriculturally acceptable salt thereof, according to claim 4 , as an active ingredient; and at least one additive component.

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

wherein n is 1, R 1 is CH 2 CF 3 , R 2 is Cl, R 3 is F, and R 4 is CH 2 CH 2 CH 2 CH 2 CH 2 SCF 3 .