WO2001032609A1 - Novel compounds having cyano and insecticides and miticides - Google Patents

Abstract

Compounds represented by general formula (1), a process for producing the same and insecticides and miticides containing as the active ingredient the above compounds or salts thereof wherein A represents one member selected from among the groups represented by A1 to A12; B represents phenyl substituted by W or a heterocyclic group substituted by W; and R represents hydrogen, C1-6 alkyl, COR1, CSR1, SO2R2, C1-6 alkylcarbonyloxy (C1-6 alkyl), C3-6 cycloalkylcarbonyloxy (C1-6 alkyl) or optionally substituted phenylcarbonyloxy (C1-6 alkyl).

Description

 Specification

 Novel compounds with cyano groups and insecticides ■ Acaricides Technical field:

 The present invention relates to a novel compound, a method for producing the same, and an insecticide and acaricide.

Background art:

 Many insecticides and acaricides have been used, but their effectiveness has been insufficient, their use has been limited due to drug resistance problems, and phytotoxicity and contamination have occurred in plants. Because of its high toxicity to humans and fish and livestock, many of them are not necessarily satisfactory control agents. Therefore, there is a need for the development of a drug that can be used safely with few such disadvantages.

 Examples of the acrylonitrile compound similar to the compound of the present invention include EP.18969, WO97 / 40909, W098Z426683, and W098 / 359. It is described in Publication No. 35 and Publication No. W099Z44 993.

 Further, the compound represented by the following general formula is described in Tab1eId in WO98 / 35953. However, it is not disclosed that these compounds have insecticidal and acaricidal activity.

Disclosure of the invention:

 An object of the present invention is to provide a novel compound which can be industrially advantageously synthesized, has a certain effect, and can be used safely as an insecticide and acaricide.

 The present invention

 1. —General formula [I]

Wherein A is represented by the following formulas Al, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11 and A12 Represents one selected from the group consisting of groups.

 A1 A2 A3 A4

, Y

 A5 A6 A7

 A

 ^

 ヽ

 A8 A9 A10

 A11

(Xi x ₂ , x ₃ and x ₄ each independently represent a hydrogen atom, a halogen atom, a c! S alkyl group or a c ₆ haloalkyl group,

x ₅ is hydrogen atom, - ₆ alkyl group, c _{2 s} alkenyl group, ς ₂ - δ Haroaruke represents a double group or an optionally substituted phenyl c _ ₆ alkyl group!

chi _6, chi ₇ are each independently a 〇 _{1 -6} alkyl group, also, chi _beta and chi ₇ may form a 5-8 membered ring together.

Υ is Shiano group, - _s alkyl, C ₃ - s cycloalkyl group, in optionally substituted Hue sulfonyl ₍₁ - ₆ alkyl group, a phenyl group which may be substituted with G _t, in substituted which may phenoxy group, G may phenoxy CJ be substituted with _{t '6} alkyl group, in optionally substituted phenylene group, a heteroarylthio group, in optionally substituted phenylene thioether C i ₆ alkyl group, in which substituted which may Hue Nils sulfinyl group which may be substituted by G _t Fuenirusurufu Iniru C ^ ₆ alkyl group, in optionally substituted phenylalanine alkylsulfonyl be group, an optionally substituted phenylalanine sulfonyl with Gi (! _ ₆ alkyl group, in optionally substituted Anirino group, in optionally substituted Anirino C i ₆ alkyl group, in an optionally substituted thienyl group, in optionally substituted thienyl C ₆ alkyl group, substituted by G _t Piri Le based on And optionally pyridyl C! It represents one group selected from the group consisting of _ ₆ alkyl group.

Z represents an oxygen atom, a sulfur atom or, even in properly hydrogen atom - ₆ alkyl group represents a nitrogen atom that substitute.

Is nitro group, Shiano group, a halogen atom, C! E alkyl group, C _{2 6} alkenyl, C _{2 6} alkynyl group, C ₃ _ ₈ cycloalkyl group, C i ₆ haloalkyl group, C ₂ Bruno, Roarukeniru group, ₆ alkoxy, C i-s haloalkoxy, C ₂₆ alkenyloxy, C ₂₆ haloalkenyloxy, C ₂₆ alkynyloxy, ₆ alkylthio, — ₆ alkylsulfiel, C i ₆ alkylsulfonyl groups, C! _β § Rukiruami Roh group, a di - ₆ alkylamino amino group, door Li - ₆ alkylsilyl, C ^ ₆ § alkoxy 0 ₁ - ₆ alkyl group, - ₆ alkylthio C - ₆ alkyl group, - ₆ alkyl Rusurufiniru. _1-6 alkyl group, c ₆ alkylsulfonyl 0 i ₆ alkyl group, C

1 _ ₆ alkyl group, - ₆ alkoxycarbonyl group, phenyl optionally substituted with G ₂ C i-e alkyl group, optionally substituted with G ₂ Hue sulfonyl 〇 i ₆ alkoxy group, substituted with G ₃ are also good thienyl group, an optionally substituted pyridyl group G _2, G ₂ which may be substituted with Pirijiruokishi group, an optionally substituted phenyl group G _4, enoxy off may be substituted by G ₄ Represents a group.

G ₂ is - ₆ alkyl group, a halogen atom, C i ₆ haloalkyl group or a C i Roh represents a Roarukokishi group.

G ₃ represents a C i ₆ alkyl group or a halogen atom.

G ₄ are nitro group, Shiano group, a halogen atom, - ₆ alkyl group, C ₆ Haroaruki group, - 6 alkoxy group, - ₆ haloalkoxy group, an alkylthio group,

_ ₆ alkylsulfinyl group, C -! ₆ alkylsulfonyl group, ₆ Arukiruamiso group, di 〇 ₁ - ₆ alkylamino group, - ₆ alkylcarbonyl group, - represents a 6 alkoxy force Lupo two Le group. )

 B represents a phenyl group substituted with W or a heterocyclic group substituted with W.

Here, W is a nitro group, Shiano group, a halogen atom, C i-e alkyl group, C ₃ _ ₈ cyclo alkyl group, - ₆ haloalkyl group, - ₆ alkoxy group, - ₆ Haroarukoki sheet group, C! - ₆ alkylthio groups, C ₆ alkylsulfinyl group, - ₆ alkylsulfinyl Honiru group, - ₆ alkylamino amino group, di - ₆ alkylamino group, - ₆ alkyl force Ruponiru group, C ie alkoxycarbonyl group is substituted with G ₅ which may be phenyl group, optionally substituted by G ₅ represents an phenoxy group,

G ₅ is a nitro group, Shiano group, a halogen atom, C -! Alkyl, C i-e Haroaruki group, - ₆ alkoxy group, - ₆ haloalkoxy group, C i-e alkylthio group, (丄_ ₆ alkyl sulfinyl group, C i_ ₆ alkylsulfonyl group, - ₆ alkylamino Bruno It represents ₆ alkoxy force Lupo two group, - group, di 0 ₁ - ₆ alkylamino group, c ₆ alkylcarbonyl group,

 The heterocyclic group substituted with w is a triazolyl group, a thiazolyl group, an oxazolyl group, an isoxazolyl group, an isothiazolyl group, a pyrazolyl group, an imidazolyl group, a tetrazolyl group, an oxaziazolyl group, a thiadiazolyl group, a chenyl group, a furyl group, or a pyrrolyl group. Group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, and a birazinyl group.

R is a hydrogen atom, C i_ ₆ alkyl group, a group represented by the formula CO Ri, a group represented by the formula CS Ri, a group represented by S 0 ₂ R _2, - ₆ alkylcarbonyl O alkoxy C i- 6 alkyl group, C ₃

Representing the _ ₆ cycloalkylcarbonyl O alkoxy C alkyl group or an optionally substituted full E sulfonyl carbonyl O carboxymethyl C! _ ₆ alkyl group.

(Here, C ^ _{1 2} alkyl group, C _{3 6} cycloalkyl group, ₍₆ Haroaruki Le group, C _i-6 alkoxy group, C! ₆ alkylthio group, _alkyl amino group, di C! _ ₆ alkylamino group, which may have a substituent Hue nil. i ₆ alkyl group, and display the good phenylene Le group optionally having a good phenyl CJ _ ₆ alkoxy group or a substituted group which may have a substituent, R ₂ represents a C i_ ₁₂ alkyl group or a phenyl group which may have a substituent.)

However, B is a pyridyl group substituted with a phenyl group or a W substituted with W, and, R is a hydrogen atom, C i ₆ alkyl group, a group represented by the formula CO Ri, is represented by the formula CSI ^ In the case of a group represented by the formula: or a group represented by S 0 ₂ R ₂ , A is not a benzyl group substituted by A compound represented by the formula:

2. General formula (3) ヽ

(Where A represents the same meaning as in claim 1), and a compound represented by the general formula (4) o

 B (4)

(Wherein B has the same meaning as in claim 1 and L represents a leaving group.) A compound represented by the general formula (2) characterized by reacting in the presence of a base group:

(Wherein, A and B have the same meanings as described above).

3. General formula (5)

(Wherein B has the same meaning as in claim 1) and a compound represented by the general formula (6):

 A- L '

 (Wherein A has the same meaning as in claim 2 and L ′ represents a leaving group). The compound represented by the general formula (2), Manufacturing method of and

4. An insecticide and acaricide containing the compound represented by the general formula [I] or a salt thereof as an active ingredient. Embodiment of the invention:

 In the general formula [I],

 A represents any of the groups represented by the above formulas A 1 to A 12.

In the formula, X ₁ X ₂ , X ₃ and X ₄ are each independently a hydrogen atom,

 Halogen atoms such as fluorine, chlorine, bromine and iodine,

Methyl, Echiru, n-propyl, isopropyl, n- butyl, sec- heptyl, isobutanol chill, t -! Heptyl, n- pentyl and its isomers, hexyl and C _ ₆ alkyl group isomers thereof, etc., to n-, Or

 Represents C haloalkyl groups such as chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, trichloroethyl, trifluoromethyl, pentafluoroethyl and the like.

X ₅ is a hydrogen atom,

Methyl, Echiru, n-propyl, isopropyl, n- butyl, sec- heptyl, isobutanol chill, t one heptyl, n- pentyl and its isomers, hexyl and C! _ ₆ alkyl group isomers thereof, etc., to n-,

Ethenyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-12-propenyl, 1-pentenyl, Two —Pentyl, 3 —pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-2-butenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-to C ₂ such cyclohexenyl - ₆ alkenyl group,

3—chloro-2-propenyl, 4-chloro-2-butenyl, 4,4-dichloro-3- (butenyl), 4,4-difluoro-3-butenyl, 3,3-dichloro-2-C ₂ — ₆ haloalkenyl groups, or

Phenylmethyl, 1-phenylethyl, 2-phenylphenyl, 3-phenylpropyl, 4-phenylbutyl, (2-chlorophenyl) methyl, (4-methylphenyl) methyl, 3-nitrophenylmethyl, (4-methoxyphenyl) methyl , (3,5-difluorophenyl) methyl, 2- (4-chlorophenyl) ethyl, 2- (4-methylphenyl) ethyl, and 2- (3,4-dibromophenyl) ethyl Represents a phenyl i- ₆ alkyl group which may be substituted.

X ₆ and X ₇ are each independently methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isoptyl, t-butyl, pentyl and its isomers, hexyl and its isomers Represents a Ci- ₆ alkyl group.

X ₆ and X ₇ may be taken together to form a ring having 5 to 8 carbon atoms. Examples of such a ring having 5 to 8 carbon atoms may have a substituent (cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl).

 Y is a cyano group,

Methyl, Echiru, n - Buropiru, isopropyl, n- heptyl, sec - heptyl, isobutanol chill, t one heptyl, n- pentyl and its isomers, n -! Hexyl and C _ ₆ alkyl group of the isomers thereof,

Cyclobutyl pill, 1-methylcyclopropyl, 2,2,3,3-tetramethylcyclopentyl, cyclobutyl, cyclopentyl, 1-methylcyclopentyl, cyclohexyl, 1-methylcyclohexyl, 4-methylcyclohexyl, etc. an optionally substituted C ₃ - ₈ consequent opening alkyl group,

Optionally substituted phenyl C — ₆ alkyl group, G! A phenyl group optionally substituted with, a phenoxy group optionally substituted with, a phenoxyalkyl group optionally substituted with, a phenylthio group optionally substituted with, a phenylthio group optionally substituted with C! _ ₆ alkyl group, in which may be substituted Hue Nils Luffy El group, in which may be substituted Hue Nils sulfinyl 〇, an alkyl group, in which may be substituted Fuenirusuru Honiru group, in which may be substituted good phenylalanine alkylsulfonyl C i _ ₆ alkyl group, in unsubstituted or Yoi Anirino group, in optionally substituted Anirino CL- ₆ alkyl group, in which may be substituted 2 - also is properly Choi two Le group 3 - thienyl group, in optionally substituted thienyl C _ ₆ alkyl group, in which may be substituted 2 - pyridyl, 3 - pyridyl is properly 4 one Represent an Pyridyl C i _ ₆ alkyl group optionally substituted by a pyridyl or G _t.

 Where is a nitro, cyano,

 Halogen atoms such as fluorine, chlorine, bromine and iodine,

Methyl, Echiru, n-propyl, isopropyl, n- heptyl, sec -! Butyl, isobutanol chill, t one-heptyl, n- Benchiru and its isomers, hexyl and C _ ₆ alkyl group isomers thereof, etc., to n-,

Ethenyl, 1-propenyl, 2-butenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2— Pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, etc. C ₂ - ₆ alkenyl group,

Etul, 1-propier, 2-propier, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-vinyl, 2-methyl-3-butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4 one pentynyl, 1 one methyl one 2 - Bucheru, 2-methyl-one 3 - pentynyl, 1 - to hexynyl, 1, 1 - dimethyl one 2 - C ₂ such heptynyl - ₆ Al Kiniru group,

Such as cyclopropyl, 1-methylcyclopropyl, 2,2,3,3-tetramethylcyclopropyl, propyl, cyclobutyl, cyclopentyl, 1-methylcyclobentyl, cyclohexyl, 1-methylcyclohexyl, 4-methylcyclohexyl, etc. an optionally substituted C ₃ - ₈ consequent opening alkyl group,

Ci- ₆ haloalkyl groups such as chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, trichloroethyl, tolufluoroethyl, and pentafluoroethyl;

3 —Black mouth 2 —Propenyl, 4 Black mouth 2 —Butur, 4,4 Dichloro mouth 3 —Butenyl, 4,4 Difluoro-3-butenyl, 3,3-Dichloro-2-propylene, etc. The C

2 _ ₆ haloalkenyl group,

_6- alkoxy groups such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, t-butoxy,

C, such as chloromethoxy, dichloromethoxy, trichloromethoxy, trifluoromethoxy, 1-fluoroethoxy, 1,1 difluoroethoxy, 2,2,2—trifluoroethoxy, pentafluoroethoxy, etc. _ ₆ haloalkoxy group,

Ariruokishi, 2 - propenyl Niruokishi, 2 Buteniruokishi, C ₂ and 2-methyl-3-propenyl Niruokishi - ₆ Arukeniruokishi group,

3 —Chloro 2- 2-propenyloxy, 3,3-Dichloro 1-2 -propynylooxy, 4-chloro-1,2-butenyloxy, 4,4-Dichloro-3-butenyloxy, 4,4 difur C ₂ — ₆ haloalkenyloxy groups such as Oloh 3-butenyloxy,

C ₂ _ ₆ alkynyloxy groups such as 2 —propinyloxy, 2 —butynyloxy, 1 —methyl-2-propynyloxy,

Methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, t-butylthio, etc. Ci- ₆ alkylthio groups, methylsulfiel, ethylsulfinyl, propylsulfinyl, butylsulfinyl Alkylsulfinyl group such as

C! For methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, etc. _ ₆ alkylsulfonyl group,

 Ci-e alkylamino such as methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isoptylamino, sec-butylamino, t-butylamino, 1-methylbutylamino, n-pentylamino, etc. Group,

Jimechiruami Bruno, Jechiruamino, Jipuropiruami Bruno, Jibuchiruami Bruno, Echiruisopu port Piruamino, di C i _ ₆ alkylamino amino group such as methyl propyl amino

Tri-C i- ₆ alkylsilyl groups such as trimethylsilyl,

C 1-6 alkoxy C i- ₆ alkyl group such as methoxymethyl, methoxethyl, ethoxymethyl, propoxymethyl, butoxymethyl,

Ci- ₆ alkylthio- ₆ alkyl groups such as methylthiomethyl, methylthioethyl, ethylthioethyl, ethylthiomethyl, propylthiomethyl, and butylthiomethyl;

Methylsulfinyl, methyl sulfide El E chill, E chill sulfinyl Rue chill, E chill sulfinyl methyl, propyl sulfinyl methyl, Buchirusurufi two Rume, chill, etc. ^ - ₆ alkylsulfinyl C _i-6 alkyl group,

₆ § alkylsulfonyl - - ₆ alkyl group, methylsulfonylmethyl, C methylsulfonyl E chill, E chill sulfonyl E chill, Echiru sulfonyl methyl, propyl sulfonyl methyl, heptyl sulfonyl methyl and the like

 C such as methylcarbonyl, ethylcarbonyl, propylcarbonyl, butylcarbon

! _ ₆ alkylcarbonyl group,

Main butoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxy force Ruponiru, butoxycarbonyl, t one butoxycarbonyl C E of - _fi alkoxycarbonyl group,

Phenyl optionally substituted with G ₂ i- ₆ alkyl group, phenyl optionally substituted with G ₂

A C _x _ ₆ alkoxy group, a phenyl group optionally substituted with G ₃ , a pyridyl group optionally substituted with G ₂ , a pyridyloxy group optionally substituted with G ₂ , a phenyl group optionally substituted with G ₄ Represents a phenyl group which may be substituted by a diyl group or G ₄ .

Where G ₂ is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec C-e alkyl groups such as monobutyl, isobutyl, t-butyl, n-pentyl and its isomers, n-hexyl and its isomers,

 Halogen atoms such as fluorine, chlorine, bromine and iodine,

 Ci-6 haloalkyl groups such as chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, trichloroethyl, trifluorofluoryl, pentafluoroethyl, etc .; Is

Chloromethoxy, fluoromethoxy, promomethoxy, dichloromethoxy, difluoromethoxy, dibromomethoxy, trichloromethoxy, trifluoromethoxy, tribromomethoxy, 2,2,2—trichloromouth ethoxy, 2,2,2 — Represents Ci- ₆ haloalkoxy groups such as trifluorofluoro, pentafluoroethoxy, and perfluoropoxy.

G ₃ is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isoptyl, t-butyl, n-pentyl and its isomers, n-hexyl and its isomers, and the like. _6- alkyl group, or

 Represents a halogen atom such as fluorine, chlorine, bromine and iodine.

G ₄ is a nitro group, a cyano group,

 Halogen atoms such as fluorine, chlorine, bromine and iodine,

Methyl, Echiru, n - propyl, isopropyl, n - heptyl, sec - butyl, isobutanol chill, t-butyl, n -! Pentyl and its isomers, hexyl and C _ ₆ alkyl group isomers thereof, etc., to n-,

Chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, 2,2,2—trichloroethyl, 2,2,2—trifluoroethyl, pentafluoro C _ ₆ haloalkyl groups such as loethyl,

 C t-e alkoxy groups such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, t-butoxy,

Ci- ₆ haloalkoxy groups such as chloromethoxy, dichloromethoxy, trichloromethoxy, trifluoromethoxy, 1-fluoroethoxy, 1,1-difluoroethoxy, methylthio, ethylthioethyl, n-propylthio, isopropylthio, n-butylthio , Isobutylthio, sec-butylthio, t-butylthio and other Ci- ₆ alkylthio groups, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, n-butylsulfinyl and other _6- alkylsulfinyl groups,

'C- ₆ alkylsulfonyl groups such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, n-butylsulfonyl,

Methylamino, ethylamino, n-Proviramino, isopropylamino, n-butyl C 1-6 alkylamino groups such as amino, isobutylamino, sec-butylamino, t-butylamino, n-methylbutylamino, n-pentylamino, etc.

 Di-C-alkylamino groups such as dimethylamino, getylamino, dipropylamino, dibutylamino, ethylisopropyl pyramino, and methylpropylamino;

 A C-ealkylcarbonyl group such as methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, n-butylcarbonyl, or

 Represents a Ci-alkoxycarbonyl group such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, and t-butoxycarbonyl.

 Z is an oxygen atom, a sulfur atom, or a hydrogen atom or a C ^ -alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isoptyl, t-butyl, etc. Represents a nitrogen atom. )

Represents one kind of group selected from the groups represented by

 B represents a phenyl group substituted with W or a heterocyclic group substituted with W.

 Where W is a nitro group, a cyano group,

 Halogen atoms such as fluorine, chlorine, bromine and iodine,

Methyl, Echiru, n-propyl, isopropyl, n- heptyl, sec- heptyl, isobutanol chill, t - heptyl, n- pentyl and its isomers, hexyl and C _t _ ₆ alkyl group isomers thereof, etc., to n-,

 C— „cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.,

 Chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, 2,2,2-trichloroethyl, 2,2,2-trifluoroethyl, pentafluoro C such as Loetil

! _ ₆ haloalkyl group,

_6- alkoxy groups such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, t-butoxy,

C- _6- nitroalkoxy groups such as chloromethoxy, dichloromethoxy, trichloromethoxy, trifluoromethoxy, 1-fluoroethoxy, 1,1-difluoroethoxy, methylthio, ethylthio, n-propylthio, isopropyl building thio, n- Puchiruchio, I Sobuchiruchio, sec- Puchiruchio, C alkylthio group such as t one Puchiruchio, methylsulfinyl, E chill sulfinyl, propyl sulfinyl, Puchirusurufi two Le etc. - ₆ alkylsulfinyl group,

_6- alkylsulfonyl groups such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, n-butylsulfonyl, Ci-e alkylamino groups such as methylamino, n-propylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino, sec-butylamino, t-butylamino, 1-methylbutylamino, n-bentylamino, etc.

Jimechiruamino, Jechiruami Bruno, Jipuropiruami Bruno, Jibuchiruami Bruno, Echiruisopu port Piruamino, di C i _ ₆ alkylamino amino group such as methyl propyl amino,

_6- alkylcarbonyl groups such as methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, n-butylcarbonyl, etc.

Main butoxycarbonyl, ethoxycarbonyl, n - propoxycarbonyl, Isopuropoki aryloxycarbonyl, n - butoxycarbonyl, t - butoxy C _i-6 an alkoxy group such as a carbonyl or optionally substituted with G _5, (phenyl group or phenoxy Base).

Where G ₅ is a nitro group, a cyano group,

 Halogen atoms such as fluorine, chlorine, bromine and iodine,

_6- alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, etc.

Ci-e haloalkyl groups such as chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, trichloroethyl, trifluoromethyl, pentafluoroethyl, etc .; butoxy, ethoxy, n- Purobokishi, Isopurobokishi, n - butoxy, sec - butoxy, isobutoxy, t one butoxy (: E - ₆ alkoxy group,

Chloromethane butoxy, Jikurorome butoxy, preparative Rikurorome Bok alkoxy, Application Benefits Furuorome Toki. Shi, 1 one Furuoroetokishi, 1, -1-difluoromethyl O b C ₆ haloalkoxy groups ethoxy, methylthio, Echiruchioechiru, n- propylthio, isopropylthio, n - Buchiruchi O, Isopuchiruchio, sec - ₆ alkylsulfide El group, - Puchiruchio, t C _i-6 alkylthio groups such as one Puchiruchio, C ^ such methylsulfinyl, E chill sulfinyl, propyl sulfinyl, Buchirusurufi two Le

C! For methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, etc. _ ₆ alkylsulfonyl group,

 Ci-s alkyls such as methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isoptylamino, sec-butylamino, t-butylamino, 1-methylbutylamino, n-bentylamino, etc. Amino group,

 Dialkylamino groups such as dimethylamino, getylamino, pyruvamino dibu, dibutylamino, ethylisopropyl pyramino, methylpropylamino, methylbutylamino, etc.

C such as methylcarbonyl, ethylcarbonyl, propylcarbonyl, butylcarbonyl, etc. ! _ ₆ alkylcarbonyl group, or

It represents a butoxy C i_ ₆ alkoxy Shikarubo two Le group such as carbonyl - main butoxycarbonyl, ethoxycarbonyl, n- propoxycarbonyl, Isopuropoki aryloxycarbonyl, n- butoxycarbonyl, t.

 As the heterocyclic group substituted by W, a 5- or 6-membered heterocyclic group containing 1 to 4 nitrogen atoms, oxygen atoms or sulfur atoms is preferable, for example, 2-furyl, 3-furyl, 2-furyl. —Chenil, 3—Chenyl, Pyrrole 1-yl, Pyroyl 41-yl, Oxazo 1-ru 2-yl, Oxazo 1-41-yl, Oxazo 1-ru 5-yl, Isoxoxazo 1 Lou 3-yl, Isoxazole 1-yl, Isoxazolu 5-yl, Thiazolu 2-yl, Thiazoll 4-yl, Thiazolu 5-yl, Iso Thiazole 1-3-yl, Isothiazole 1-4-yl, Isothiazo-1-yl 5-yl, Birazol 1-3-yl, Pyrazol 41-yl, Imidazo-1 2-yl, Imidazole-41 1-, 2-, 4-, 3-, 5-, 3-, 3-, 5-, 3—triazolu 4—yl, tetrazoyl, 1,

2, 4-Oxaziazo 1-3-yl, 1, 2, 4-Oxaziazo-5-yl, 1,

3,4, -Oxaziazolu 2-yl, 1,3,4-Oxaziazolo 5-yl, 1,2,4-thiadiazol 3-yl, 1,2,4-thiadiazolu-5- 1,3,4-thiazolyl 3-yl, 1,3,4-thiazoyl 5-yl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 5-pyridyl, 3-pyridazinyl , 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 2-virazinyl and the like.

 R is a hydrogen atom,

C alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, pentyl and its isomers, hexyl and its isomers, represented by the formula CO Rt that group, a group衷formula CS Ri, a group represented by S 0 ₂ R _2, § Se Tokishimechiru, Viva Roy Ruo carboxymethyl, hepta Noi Ruo carboxymethyl, § Se butoxy Echiru, hexyl or the like to § Se butoxy Alkyl carboxy <3 _t — ₆ alkyl group, cyclopropyl carbonyl oxymethyl, cyclopentyl carbonyl oxymethyl, cyclohexyl carbonyl oxymethyl, cyclo propyl carbonyl oxethyl, cyclo propyl carbonyl oxy of cyclohexane and the like C - ₆ consequent opening alkylcarbonyl O alkoxy C _{1 - 6} alkyl group or a

Base may have a substituent emission zone I Ruo carboxymethyl represents phenylalanine carbonyl O carboxymethyl C! _ ₆ alkyl groups such as 2- (Benzoiruokishi) Echiru.

 Where is: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, n-pentyl and its isomers, n-hexyl and its isomers, n —Heptyl and its isomers, n-nonyl and its isomers, n-dodecyl, etc.

C! ₂ alkyl groups, ₆ cycloalkyl group, - cyclopropyl, cyclobutyl, cyclopentyl, C ₃ of cyclohexyl like cyclohexane

C. Oral methyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, trichloroethyl, tolufluoroethyl, pentafluoroethyl, etc. 6 haloalkyl groups, methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy, t-butoxy, etc.- ₆ alkoxy groups,

Methylthio, Echiruchio, n - propylthio, isopropylthio, n - Puchiruchio, I Sobuchiruchio, sec - Puchiruchio, t - C i _ ₆ alkylthio groups such Puchiruchio, Mechiruami Bruno, Echiruami Bruno, n- Puropiruami Roh, isopropyl § Mi Bruno, n—Butylamino, isobutylamino, sec—butylamino, t—butylamino, 1-methylbutylamino, n—pentylamino, and other CJ- ₆ alkylamino groups,

 Di-C-alkylamino groups such as dimethylamino, getylamino, dipropylamino, dibutylamino, ethylisobutyrylamino, methylpropylamino and methylbutylamino;

A phenyl Ci- ₆ alkyl group which may have a substituent,

 A phenyl c alkoxy group which may have a substituent, or

 Represents a phenyl group which may have a substituent.

R ₂ is methyl, ethyl, n-propyl, isopropyl, n-butyl, isoptyl, sec-butyl, t-butyl, n-pentyl and its isomer, n-hexyl and its isomer, n-heptyl and its isomers, n - represents a nonyl and its isomers, C i "i ₂ § alkyl group or an optionally substituted phenylene group, a n- dodecyl.

Examples of the substituent of the phenyl group which may have a substituent in R 1 or R ₂ include halogen atoms such as fluorine, chlorine, bromine and iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec. — Butyl, isobutyl, t-butyl, etc. — _6- alkyl groups, chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, trichloroethyl, trichloromethyl Ci-haloalkyl groups such as fluoroethyl and pentafluorethyl; methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, and 6-alkoxy groups such as t-butoxy. Can be

Further, the substituent may have a Hue sulfonyl (- it is a ₆ Hue sulfonyl _(i-6 Al kill the alkyl group, benzyl, 1-Fueniruechiru, 2 - Fueniruechiru, 1 one-phenylene Rou 1-methylethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenylpropyl and the like, and the phenyl C i-e alkoxy group, which may have a substituent, phenyl C

! _ ₆ alkoxy groups include benzyloxy, 1-phenylethoxy, 2-phenyl Toxic, 1-phenyl 1-methylethoxy, 1-phenylpropoxy, 2-phenylpropoxy, 3-phenylpropoxy and the like.

 The compound of the present invention can be produced, for example, by the following method.

 (a) Method for producing compound (2) wherein R is a hydrogen atom 1

(Wherein A and B represent the same meaning as described above, and L represents a halogen atom, a C-e alkoxy group, a phenoxy group, a 1-imidazolyl group, a 1-pyrazolyl group, a p-toluenesulfonyloxy group (P -Represents a leaving group such as a methylphenylsulfonyloxy group), a methanesulfonyloxy group (methylsulfonyloxy group), or a trifluoromethanesulfonyl group (trifluoromethylsulfonyloxy group).

 That is, by reacting the compound represented by the formula (3) with the compound represented by the formula (4) in the presence of a base, the compound represented by the general formula (2) can be obtained.

 Bases used in this reaction include metal hydroxides such as sodium hydroxide and potassium hydroxide, carbonates such as sodium carbonate and potassium carbonate, n-butyllithium, lithium diisopropylamide (LDA) And metal hydrides such as sodium hydride and potassium hydride, and organic bases such as triethylamine, diisopropylethylamine and pyridine.

 Solvents that can be used include N, N-dimethylformamide (DMF), N, N-dimethylacetamide, dimethylsulfoxide (DMSO), and tetrahydrofuran.

(THF), acetonitrile, hexamethylphosphoramide (HMPT), benzene, toluene, dichloromethane, chloroform, carbon tetrachloride, and the like can be used. The reaction temperature is preferably in the range from 178 ° C to the boiling point of the solvent used.

 (b) Method for producing compound (2) wherein R is a hydrogen atom

(Wherein, A and B are as defined above, L 'is a halogen atom, - ₆ alkoxy group, phenoxy group, 1 one imidazolyl group, 1-pyrazolyl group, p- toluenesulfonyl O carboxymethyl A leaving group such as a methanesulfonyloxy group, a trimethanesulfonyl group, a phthalimid group, or a succinic imid group. )

 That is, a compound such as a substituted alkyl halide, substituted benzyl halide, or substituted phenyl halide represented by the formula (6), or a halogenating agent is reacted with a cyanoacetyl compound (5) in the presence or absence of a base. By doing so, the compound represented by the general formula (2) can be easily produced.

 c

 Examples of the salt J2 used in this reaction include metal hydroxides such as sodium hydroxide and potassium hydroxide, carbonates such as sodium carbonate and potassium carbonate, n-butyllithium, and lithium diisopropylamide. Organic metal such as (LDA); metal hydrides such as sodium hydride and potassium hydride; and organic bases such as triethylamine, diisopropylethylamine, pyridine and the like.

 In addition, as a solvent that can be used, DMF, N, N-dimethylacetamide, DMSO, THF, acetonitrile, HMPT, benzene, toluene, dichlorometasi, chloroform, carbon tetrachloride, etc. are used. be able to. The reaction temperature is preferably in the range from 178 TC to the boiling point of the solvent used.

 The cyanoacetyl compound represented by the general formula (5), which is a starting compound of the method of the present invention, can be easily produced, for example, by the method shown in the following formula.

(In the formula, B represents the same meaning as described above, and L ″ represents a halogen atom.)

(c) Method for producing compound (2) in which R is a hydrogen atom 1

 O

 L '

 A-L people

 O

r CO, R, (6) A 丫 C0 ₂ R ₃ (4)

 A,

 , B

CN Base CN Base NC C0 ₂ R ₃

 (7) (8) (9)

 OH

 A,

(Where A, B, L and L ′ have the same meanings as described above, L ′ is a halogen atom, p-tol R ₃ represents a leaving group such as an ensulfonyloxy group, a methanesulfonyloxy group, or a trifluoromethanesulfonyloxy group; R ₃ represents a C alkyl group; )

 First, a compound represented by the formula (8) is obtained by reacting a cyanoacetic acid ester represented by the formula (7) with a compound represented by the formula (6) in the presence of a base.

 This reaction is carried out by using a base such as sodium hydride, potassium hydride, sodium carbonate in a solvent such as DMF, DMS O, THF, acetonitrile, HMPT, or ② Phase transfer catalysts such as quaternary amine salts and metal water such as sodium hydroxide and potassium hydroxide in a two-layer solvent of benzene, toluene, dichloromethane, chloroform, and carbon tetrachloride and water. The reaction is carried out using a base such as an oxide in a temperature range from 178 to the boiling point of the solvent used.

 Next, the compound represented by the formula (8) is reacted with the compound represented by the formula (4) in the presence of a base to obtain a compound represented by the formula (9).

 This reaction is carried out in a solvent such as DMF, DMSO, THF, acetone, HMPT, benzene, toluene, dichloromethane, chloroform, carbon tetrachloride, etc. in a solvent such as sodium hydroxide and potassium hydroxide. , Sodium carbonate, potassium carbonate, n-butyllithium, lithium diisopropylamide (LDA), sodium hydride, potassium hydride, triethylamine, diisopropylethylamine, pyridine, etc. The reaction is carried out in a temperature range from 178 to the boiling point of the solvent used.

 Next, by dealkoxycarbonylating the compound represented by the formula (9), a compound represented by the formula (2) can be obtained.

 This reaction is carried out in a solvent such as water, methanol, ethanol, dimethoxetane, dioxane, DMF, DM.SO, benzene, toluene, etc., acid such as sulfuric acid, hydrochloric acid, acetic acid, P-toluenesulfonic acid, sodium hydroxide, sodium hydroxide, etc. The reaction is carried out in a temperature range from 178 ° C to the boiling point of the solvent used, using a base such as ummethoxide or triethylamine, or a metal halide such as lithium chloride or calcium chloride.

 The compound represented by the general formula (2) exists as a keto-type and an enol-type tautomer. All of these isomers are included in the scope of the present invention.

(d) A method for producing a compound wherein R is a group other than a hydrogen atom RL "

(Wherein, A, B and R have the same meanings as described above, and L "represents a halogen atom, an e- ₆ alkoxy group, a phenoxy group, a 1-imidazolyl group, an 1-pyrazolyl group, a p-toluenesulfonyloxy group. A leaving group such as a methanesulfonyloxy group or a trifluorosulfonyloxy group.)

 The compound represented by the general formula (1) can be obtained by reacting the compound represented by the general formula (2) with a compound represented by the formula (10) in a solvent in the presence of a base. it can.

 The base used in this reaction includes alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, carbonates such as sodium carbonate and potassium carbonate, and organic compounds such as N-butyllithium and LDA. Examples include metals, metal hydrides such as sodium hydride and hydrogenation hydride, and organic bases such as triethylamine, diisopropylethylamine, and pyridine.

 Examples of the solvent that can be used include DMF, DMSO, THF, acetonitril, HMPT, benzene, toluene, dichloromethane, chloroform, and carbon tetrachloride. The reaction temperature is preferably in the range from 178 ° C to the boiling point of the solvent used.

 The compound of the present invention represented by the general formula (1) has a stereoisomer represented by the formula (1 ′) as shown below, and depending on the reaction conditions and the purification method, either one of them is present. In some cases, and a mixture of isomers in some cases. All of these isomers are included in the scope of the present invention.

 (r)

 (1)

 After completion of the reaction, the desired product can be obtained by performing ordinary post-treatment. The structure of the compound of the present invention was determined from IR, NMR, MS and the like.

Representative examples of the compounds of the present invention that can be produced as described above are shown in Tables 1 to 3. The abbreviations in each table have the following meanings. Me: methyl, Et: ethyl, Pr: propyl, Bu: butyl, Ph: phenyl, Hex hexyl, n: normal, i: iso, t: Yukari, c: cyclo

 b25;, ci b26; F b27;. ci

C ^F 3 N ' ^N ' ^{Me CF} 3 N ' ^N ' ^Me Me N ' ^N ' ^Me

Me ⁰

 18

For replacement ^ 0¾ rule 26)

0 0

rl; s Me ^r2s r3

 Et X 0

 nPr IPr

^r16; s CF,

0 0 0 0

^M7; S OMe ^M8; S _0Et ^Μ9; ΠΡΓ ^r2 ° ^: nBu

19

Replacement ^ (Rule 26) o OO

 Λ O

r21; oc CI r22 r23; r24; r25;

 SMe SEt Λ SnPr Λ SiPr

O S S S S

r26; <sub>0tD `</sub> ` 27; r28; _D r29; r30;

z StBu z OMe z QnPr z SMe z IS _OC E _t t

S soo r31; A_ _ r32; A 0 D r33;. A .. ,, .. r34;

 z SnPr z SiPr z NHMe, NMe.

oos

 O O O

r43; One S-Me `` 44; -S-Et r45; -S-nPr r46; -Me

 0 O 0

H ₂ OH ₂ o H ₂ o H ₂ o

r ^47: ^ 0 ^A Me ^r48; 0½ ^r49: ^ 0 ^A nPr ^r50 = ^ O ^ iPr

H ₂ OH _? OH _? OH ₂ O

^{_{r 51: tBu r52:, 0}} nBu Γ53; Roh _{Ό "nH u ex r54; O} , cPr

_r63;

20 Replacement Form (Rule 26) Table 1

21 Replacement (Rule 26) Table 1 (continued)

 1-46 1-47 1-48

 twenty two

Replacement form (Rule 26) Table 1 (continued)

 1-70 1-71 1-72

 twenty three

Replacement form (Rule 26) Table 1 (continued)

 1-79 1-80 1 -81

 The following table exemplifies combinations of B, R and Xn of all the compounds represented by the above formulas 11-96 and 1-96.

twenty four

Replacement form (Rule 26)

9Z

ISSZ.0 / 00df / X3d 609/10 OAV Table 1 (continued)

27 Replacement ^ (Rule 26) Table 1 (continued)

28

Replacement form (Rule 26) Table 1 (continued)

BR Xn BR Xn BR Xn bl r6 one b3 r6 4-iPr b6 r6 4-CF3 bl r6 4-F b3 r6 4-tBu b6 r6 4-OCFg bl r6 4-C1 b4 r6-b6 r6 4-iPr bl r6 4-Br b4 r6 4-F b6 r6 4-tBu bl r6 2,4-F ₂ b4 r6 4-C1 b7 r6 ― bl r6 2,4-Cl ₂ b4 r6 4-Br b7 r6 4-F bl r6 2 , 4-Br ₂ b4 r6 2,4-F ₂ b7 r6 4-C1 bl r6 2,6-F ₂ b4 r6 2,4-Cl ₂ b7 r6 4-Br bl r6 2,6-Cl ₂ b4 r6 2 , 4-Br ₂ bl r6 2,4-F ₂ bl r6 4-CF3 b4 r6 2,6-F ₂ b7 r6 2,4-Cl ₂ bl r6 4-OCF ₃ b4 r6 2,6-Cl ₂ b7 r6 2,4-Br ₂ bl r6 4-iPr b4 r6 -CF3 b7 r6 2,6-F ₂ bl r6 4-tBu b4 r6 4-OCF3 b7 Γ6 2,6-Cl ₂ b2 r6 ― b4 r6 4-iPr b7 r6 -CF3 b2 r6 4-F b4 r6 4-tBu b7 r6 4-OCF3 b2 r6 4-C1 b5 r6 ― b7 r6 4-iPr b2 r6 4-Br b5 r6 4-F b7 r6 4-tBu b2 r6 2, 4-F ₂ b5 r6 4-C1 b8 r6 ― b2 r6 2,4-Cl ₂ b5 r6 4-Br b8 r6 4-F b2 r6 2,4-Br ₂ b5 r6 2, 4-F ₂ b8 r6 4- C1 b2 r6 2,6-F ₂ b5 r6 2,4-Cl ₂ b8 r6 4-Br b2 r6 2,6-Cl ₂ b5 r6 2,4-Br ₂ b8 r6 2'4-F ₂ b2 r6 -CF3 b5 r6 2,6-F ₂ b8 r6 2,4-Cl ₂ b2 r6 4-OCF3 b5 r6 2,6-Cl ₂ b8 r6 2,4-Br ₂ b2 r6 4-iPr b5 r6 4-CF3 b8 r6 2 , 6-F ₂ b2 r6 4-tBu b5 r6 4-OCFg b8 r6 2,6-Cl ₂ b3 r6 ― b5 r6 4-iPr b8 r6 -CF3 b3 r6 4-F b5 r6 4-tBu b8 r6 4-OCF3 b3 r6 4-C1 b6 r6 b8 r6 4-iPr b3 r6 4- Br b6 r6 4-F b8 r6 4-tBu b3 r6 2,4-F ₂ b6 r6 4-C1 b9 r6 b3 r6 2,4-Cl ₂ b6 r6 4-Br b9 r6 4-F b3 r6 2,4- Br ₂ b6 r6 2,4-F ₂ b9 r6 4-C1 b3 r6 2,6-F ₂ b6 r6 2,4-Cl ₂ b9 r6 4-Br b3 r6 2,6-Cl ₂ b6 r6 2,4- Br ₂ b9 r6 2,4-F ₂ b3 r6 -CF3 b6 r6 2,6-F ₂ b9 r6 2,4-Cl ₂ b3 r6 4-OCF3 b6 r6 2,6-Cl ₂ b9 r6 2,4-Br _Two Table 1 (continued)

30

Replacement form (Rule 26) Table 1 (continued)

31

Replacement form (Rule 26) 9 ^J 9 ^J * \ ίί- '

^{3 MO0 - 9 J n ff>} - 9 J ssq J 9 "l ^

9 ^J 9 ^J ssq f ^J ssq HUO¾0-9 ^J 9 ^J ssq f ^x ssq

9 ^J 9 ssq esq

³葡 ^{¾0 · 9 J esq 9 J ssq} S J esq

9 ^J esq 9 ^J esq ^J ssq

^{Z (X9 H U) N -} 9 s ^ q 9 · 1 ss ε · 1 esq Ν · 9 Interview ^{z lD-f'Z 9 J s ε} · 1 ezq

9 e Z ⁽ \ 9 ^J e ^ q ^Z \ D-9'Z ε e ^ q x9H ^u HN-9 e esq-9 e eq q ¹ esq 3ΗΝ-9 e esq 9 e ssq ε ¹ esq

^{9 WHN - 9 J sq 9 ssq} z \ D-f'Z ε · 1 s ^ q

-, s - 9-t sq one 9 Interview esq ε · ¹ esq

9 · ¹ esq S Interview esq ε Interview ssq

^{9 q 9 · 1 ssq ΐΟ ·} ε Interview esq

^{9 s ^ q esq ε · 1} esq

 —One

 ¾o¾oo- 9 ssq e-ι ssq ε + esq

9 ¹ esq 5 ¹ ssq esq

9 esq ^Λ Λ'9'Ζ S- ¹ ssq q

9 esq e ^j s ^ esq

9 q q esq ζ s

9 ^J sq esq ^Z 10-9'S ζ q

9 s ^ q ss ^Z d-9'Z Ζ ¹ ssq

9 es) - ssq ^z Interview at's Ζ ¹ ssq

9 s ^ q esq ssq

J <P-9 ^J s ^ e ^j esq

9 ^J ssq ZH.

 9 esq esq ID-f

ngu-9 ^J esq ssq d- szq

• ¾u-9 · ΐ esq s ^ q ssq

9 ^ esq ^Z \ D-9'Z esq esq

9 9 ^ q esq esq

If 9 esq ^ ュ q ^£ dDO- ssq

NO-9 esq ^z \ D-f'Z ssq TJ ssq

«X a ^U X e Η a

(^) Halla i ¾

TSS .0 / 00df / X3d 609/10 OAV εε

TSS.0 / 00df / X3d 609/10 OAV Table 1 (continued)

34

Replacement cloth (Rule 26) Table 1 (continued)

35 Replacement Form (Rule 26) Table 1 (continued)

36 Use Rule 26) Table 1 (continued)

37

Replacement form (Rule 26) Table 1 (continued)

38

Replacement form (Rule 26) Table 1 (continued)

39 Replacement Paper (Rule 26) Table 1 (continued)

40

Replacement form (Rule 26) Table 1 (continued)

41

Replacement form (Rule 26)

^ 5 Table 2

43

Replacement form (Rule 26) Table 2 (continued)

44

Replacement form (Rule 26) Table 2 (continued)

 2-57 2-58

 The following Table 組合 せ illustrates all combinations of Β and R represented by the above formulas 2-1 to 2-58.

45 Replacement ^ Paper (Rule 26) 9P

Mine ε

lSS.0 / 00df / 13d 609 / ΐθ ΟΛ \ OAV // uz-ooodTld s

Table 3 (continued)

48

Replacement form (Rule 26) Table 3 (continued)

49 Replacement Paper (Rule 26) 05

(Lecture) ^ ε ^

TSS.0 / 00df / X3d 609/10 OAV Table 3 (continued)

51 Replacement form (Rule 26) Table 3 (continued)

52

Replacement form (Rule 26) Table 3 (continued)

53

Replacement form (Rule 26) Table 3 (continued)

54

Replacement form (Rule 26) Table 3 (continued)

Table 3 (continued)

56

Replacement form (Rule 26) Table 3 (continued)

57

26 Table 3 (continued)

58

Replacement form (Rule 26) Table 3 (continued)

59

Replacement form (Rule 26) (Pest control agent)

 The compound of the present invention is useful as an active ingredient of a pesticide, particularly useful as an insecticide, an acaricide, a nematocide, a sanitary pest control agent, or a biofouling agent attached to water. . The composition containing the compound of the present invention can be preferably applied particularly as an insecticide and acaricide.

 When the compound of the present invention is actually applied, it can be used in a pure form without adding other components, and can be used in a form peculiar to general pesticides for use as pesticides, for example, wettable powders, granules Preparations, powders, emulsions, aqueous solvents, suspensions, flowables and the like.

 When solid additives are used as additives and carriers, mineral powder such as soybean grains, vegetable powder such as flour, diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite, clay, etc. Organic and inorganic compounds such as sodium benzoate, urea, and sodium sulfate are used. For liquid dosage forms, petroleum fractions such as kerosene, xylene and solvent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethylsulfoxide, alcohol, acetone, methylisobutyl Ketone, mineral oil, vegetable oil, water, etc. can be used as the solvent.

 In order to obtain a uniform and stable form in these preparations, a surfactant may be added if necessary. The surfactant is not particularly limited. Examples of the surfactant include polyoxyethylene-added alkyl ether, polyoxyethylene-added higher fatty acid ester, polyoxyethylene-added sorbitan higher fatty acid ester, and polyoxyethylene. Non-ionic surfactants such as added tristyryl ether, sulfates of alkylphenol added with polyoxetylene, alkyl naphthalene sulfonates, polycarboxylates, lignin sulfonates, alkyl naphthalene sulfones Examples include a formaldehyde condensate of an acid salt and a copolymer of isobutylene-maleic anhydride.

 The amount of the active ingredient in the preparation is preferably from 0.01 to 90% by weight, particularly preferably from 0.05 to 85% by weight. The wettable powder, emulsion, suspension, and flowable thus obtained is diluted with water to a predetermined concentration to form a suspension or emulsion, and the powder and granules are used as they are in plants or Applies to soil.

 It goes without saying that the compound of the present invention alone is sufficiently effective, but it can also be used in combination with one or more of various fungicides, insecticides and acaricides, or synergists. Representative examples of fungicides, insecticides, acaricides, and plant growth regulators that can be used by mixing with the compound of the present invention are shown below.

 Fungicide :

Kyabtan, Forpet, Thiuram, Ziram, Zineb, Maneb, Mancozeb, Provineb, Polycarbamate, Chlorotatin, Kinto Isen, Captahor, Ibrozion, Procymidone, Vinclozolin, Fluoroymid, Thimoxanil, Mebronil, Mebronil Flutolanil, pencyclon, oxycarboxin, josetyl aluminum, propamoca , Triazimefone, triazimenol, propiconazole, diclobutrazole, pitertanol, hexaconazole, microbutanyl, flusilazole, etaconazole, fluotolimazol, flutriafen, penconazole, diniconazole, cyproconazole , Fenarimol, triflumizol, prochloraz, imazalil, perfrazolate, tridemorph, fenprobimorph, trifolin, pthiobate, pyriphenox, anilazine, polyoxin, metalaxyl, oxaziryl, prolacrazole , Pyrrole ditrin, blasticidin s, kasugamycin, validamycin, dihydrostrebtomycin sulfate, benomyl, carbe Dazim, Thiophanate methyl, Himexazol, Basic copper chloride, Basic copper sulfate, Fentin acetate, Triphenyltin hydroxide, Dietofencarp, Metasulfocarp, Quinomethionate, Pinapacryl, Lecithin, Baking soda, Dithianon, Zinocap , Phenaminosulf, diclomedine, guazatine, dozine, IBP, edifenphos, mepanipyrim, fermson, triclamide, metasulfocarp, fluazinam, ethokinolac, dimetmorph, pyroquilon, techmouth phthalam, fusaride, fenazoxide. Thiabendazole, tricyclazole, vinclozolin, simoxanil, cyclobutanyl, guatatin, propamocarb hydrochloride, oxolinic acid.

 Insecticide · Acaricide:

Organophosphorus and carbamate insecticides:

 Fenthion, phennitrothion, diazinon, chlorpyrifos, ESP, pamidothione, fentoate, dimethoate, formotione, marathon, trichlorfon, thiometon, phosmet, dichlorvos, acephate, EPBP, methylparathion, thioxime, thioxime Salithione, cyanophos, isoxathion, pyridafenthion, phosalon, methidathion, sulph CIphos, chlorfenvinphos, tetrachlorvinphos, dimethylvinphos, propaphos, isofenphos, ethylthiomethone, profenophos, pyraclophos, monocarphophos, alcarphos , Mesomil, Chozikarp, Carbofuran, Carbosulfan, Benfracarb, Fratioka Flop, Buropokisuru, B P M C ;, M T M C M I P C ;, force Rubariru, pyridinium Mikabu, Echiofue Nkarupu, Fuenokishikarupu, cartap, Ji old cyclam, bensultap and the like.

Pyrethroid insecticides:

 Permethrin, sibermethrin, deltamethrin, fenvalerate, fenpropatrin, pyrethrin, allesulin, tetramethrin, resmethrin, dimesulin, propasulin, phenothrin, prototrin , Fluvalinate, cyflutrin, cyhalotrin, flucitrinate, etofenprox, cycloprotrin, tralomethrin, silafluophene, brofenprox, aclinatrin and the like.

Benzoylurea and other insecticides: Difluvenzuron, chlorfluazuron, hexaflumuron, triflumuron, tetrabenzuron, flufenoxuron, flucycloxuron, buprofezin, pyriproxyfen, methoprene, benzepin, diafentiuron, imidacloprid, Fipronil, nicotine sulfate, rotenone, metaaldehyde, machine oil, microbial pesticides such as BT and entomopathogenic viruses.

Nematicide:

 Fenamiphos, phosthiazetate, etc.

Acaricide:

 Chlorbenzylate, fenisobromolate, dicofol, amitraz, BPPS, benzomate, hexthiazox, fenbutatin oxide, polynactin, quinomethione, CPCBS, tetradiphone, avermectin, milbemectin, clofentezin, cihexatin, Pyridabene, fenpyroxime, tebufenvirad, pyrimidifene, phenothocalp, dienochlor, etc.

Plant growth regulator:

 Gibberellins (eg, gibberellin A3, gibberellin A4, gibberellin A7), IAA, NAA and the like.

 The compound of the present invention can be used for controlling agricultural pests, sanitary pests, storage pests, clothing pests, house pests, and the like, and has an insecticidal, nymphalidic, larvicidal, and ovicidal action. The following are typical examples.

 Lepidopteran pests, for example, Hasmonyoto, Totoga, Tamanayaga, Aomushi, Tamanaginba, Konaga, Tyano Kokakumonhamaki, Chiyamamaki, Momoshingiga, Nashihimeshinkui, Mikanhamoguriga, Chinohogaga, Koganogama Biancon Borra, American Whitebird, Suzimada Lameiga, Heliotis, Helicobelpa, Agrotis, Iga, Kodlinga, Petakamimushi, etc.

 Hemiptera pests, for example, peach aphid, peter aphid, mosquito aphid, wheat viviparous beetle, scorpion beetle, stag beetle, anopheles mosquito, lycopodium cylindris, lycopodium lice, white lice, and white lice Coleoptera, Pterodactyla, Pterodactyla, Pterodactyla serrata, Coleoptera japonicus, etc., Coleoptera insects, for example, Cypridina beetle, Periphyll beetle, Colorado potato beetle, Rice porphyra, Kokuzumushi, Azukizomushi, Ogyukota, Oxalus Pine beetle, Sesame beetle, Sesame beetle, Agryotis,

Diptera pests, for example, house flies, oak fly, sarcophagid flies, perilla flies, mandarin fruit flies, seed flies, rice leaf maggots, key flies, sand flies, and sand flies Cayer power, Anetaishima power, Shinahamadara power, etc.

 Hymenoptera pests, for example, southern thistle ゥ; Chrysanthemum thistle, etc., Hymenoptera, pests, for example, pygmy ant, yellow-horned wasp, force-bumblebee, etc.

 Orthoptera pests, for example, Tonosa-sama grasshopper, Chinese cockroach, Scarlet cockroach, Japanese black cockroach, etc.

 Isoptera pests, for example, house termites, mountain termites,

 Lepidopteran pests, such as rodents, louse Pests, such as rodents,

 Mites, for example, Namihadani, Nisenamihadani, Kanzahadani, Citrus spider mite, Lingo red mite, Citrus avidani, Lingo savidani, Chianohoko lidani, Brevipalpas spp.

 Plant-parasitic nematodes, for example, sweet potato nematode, negusarecentiyu, soybean cistocentiyu, rice singarecentiyu, matsunoza centiyu, and the like.

 Pests that are preferably applied include lepidopteran pests, Hemiptera pests, Coleoptera pests, Pteridophytes pests, and two kinds of spiders, particularly preferably Lepidoptera pests, Hemiptera pests, two kinds of spiders It is.

 In recent years, many insect pests and mites, such as moth moth, pinworms, leafhoppers, aphids, and asters, have developed resistance to organic phosphorus agents, carbamates, and acaricides, and the lack of efficacy of these agents has occurred. Therefore, there is a need for a drug that is effective against insects and mites that are resistant to strains. The compound of the present invention is an agent having an excellent insecticidal and acaricidal effect against not only susceptible strains but also pests of organic phosphorus, carbamate, and pyrethroid-resistant strains, and mites of acaricide-resistant strains. .

 The compound of the present invention has low phytotoxicity, low toxicity to fish and warm-blooded animals, and is a highly safe drug.

 Further, the compound of the present invention can also be used as an antifouling agent for preventing aquatic organisms from adhering to aquatic organisms such as ship bottoms and fish nets. BEST MODE FOR CARRYING OUT THE INVENTION:

 Next, the present invention will be described in more detail with reference to examples.

 Example 1

Production of Y-phenyl-1-α- (2-trifluoromethylbenzoyl) ptyronitrile (Compound No. 10-1)

To a suspension of 1.54 ml of tetrahydrofuran (THF) containing 1.44 g of 2-trifluoroethyl benzoate and 1.39 g of hydrogen hydride (oil; 35%) was added. 0.8 g of phenylbutyronitrile was added dropwise under ice-cooling, followed by stirring at room temperature for 1 hour.Aqueous saturated ammonium chloride solution was added to the reaction solution, extracted with getyl ether, and the organic layer was washed with water and concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane = 1-3) to obtain 1.74 g of the desired compound.

1H-NMR (CDC 13, δ ppm): 2.30 (q, 2H), 2.75-2.88 (m, 1H), 2.94—3.05 (m, 1 H), 3.95 (t, 1H), 7.18-7.45 (m, 6H), 7.60-7.70 (m, 2H), 7.75 -7.80 (m, 1 H) Example 2

 Preparation of a- (2-phenylethyl) -1-3-bivaloyloxy 3- (2-trifluoromethylphenyl) acrylonitrile (Compound No. 4-1)

Dissolve 1.0 g of y-phenyl-1-ct-1- (2-trifluoromethylbenzoyl) ptyronitrile in 10 ml of THF, and add 0.38 g of triethylamine and 0 vivaloyl chloride under ice-cooling. After adding sequentially 46 g, the mixture was stirred at room temperature for 2 hours. The precipitated crystals were filtrated, the filtrate under reduced pressure enrichment to obtained crude product by silica force gel column chroma preparative chromatography; purified (developing solvent hexane = 1 5 to acetic Echiru Z _n), the objective compound 0.9 0 g was obtained. Yield 71% Melting point 80-82 ° C Example 3

 Preparation of a- (5-chloro-1-methyl-3-trifluorotrifluorovirazole-41-yl) carbonyl-γ- (4-chlorophenyl) ptyronitrile (Compound No. 10-2)

1) Production of tert-butyl Ί- (4-chlorophenyl) -α-cyanobutyrate

4-Chlorophenethyl alcohol (3.0 g) was dissolved in 45 ml of ethyl ether, and 0.5 g of 2,6-lutidine, 6.28 g of triphenylphosphine and carbon tetrabromide were dissolved. .62 g were sequentially added at room temperature, followed by stirring overnight. The precipitated crystals were filtered and concentrated under reduced pressure. A crude product obtained was suspended in n-hexane, further filtered and concentrated under reduced pressure. The crude product obtained here was dissolved in n-hexane, washed with 5% aqueous hydrochloric acid, concentrated under reduced pressure, and 4-chlorophenethyl bromide 5.

84 g was obtained as a crude product.

 1H-NMR (CDC 13, δ ppm): 3.13 (t, 2Η), 3.54 (t, 2Η), 7.14 (t, 2Η), 7.2 9 (t, 2Η) Dissolve 5.84 g of crude 4-chlorophenethyl bromide in 20 ml of acetonitrile, and add 1.62 g of tert-butyl cyanoacetate and 1.5 g of potassium carbonate. 9 g were sequentially added, and the mixture was heated under reflux overnight. The precipitated salt was filtered, and the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (developing solvent: ethyl acetate Zn hexane = 1 to 15) to obtain the desired compound 1.70. g was obtained. Tota 1 yield of 2 steps 6 3%

 1H-NMR (CDC 13, δ ppm): 1.5 (s, 9H), 2.20 (q, 2H), 2.73-2.91 (m, 2H) , 3.3 3 3 (t, 1H), 7.14 (d, 2H), 7.2

9 (d, 2 H)

2) Tertiary butyl a-(5-chloro-1-methyl-3-trifluoromethylvillazo-4-yl) carbo-carbonyl γ-(4-chloro-phenyl)-α-cyanobutyrate

 Dissolve 1.70 g of tert-butyl di- (4-chlorophenyl) -α-cyanobutyrate in 30 ml of toluene, and add 0.68 g of triethylamine, 0.4-dimethylaminoviridine. 20 g and 5 —Chloro-1-methyl-3 —Trifluoromethylpyrazolyl 4 —Carboxylic acid chloride 1.80 g of toluene 5 ml solution were added sequentially under ice-cooling, and then heated for 2 hours Refluxed. The precipitated crystals were filtered, and the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (developing solvent: ethyl acetate Zn hexane = 14) to obtain 2.23 g of the desired compound. Was. Yield 75%

1H— NMR (CDC 13, δ ppm): 1.49 (s, 9H), 2.32-2.42 (m, 1H), 2.59-2.73 ( m, 3H), 3.99 (s, 3H), 7.19 (d, 2H), 7.30 (d, 2 H)

3) a- (5-Chloro-1-methyl-1-3-trifluoromethylpyrazole-41-yl) Power Luno-r-γ-((4-chlorophenyl) phenyl) Production of ptyronitrile

 α-tert-butoxycarbonyl α- (5-chloro-1-11-methyl-3- 3-trifluoromethylpyrazole-14-yl) carbyl y- (4-chlorobutenyl) ptyronitrile 1.1 0 g was dissolved in 10 ml of toluene, 0.1 g of p-toluenesulfonic acid monohydrate was added, and the mixture was heated under reflux for 2 hours. The reaction solution was concentrated under reduced pressure, and the resulting crude product was purified by silica gel column chromatography (developing solvent: ethyl acetate Zn hexane = 1 Z 2) to obtain 0.69 g of the desired compound.

 Yield 80% Melting point 7 5— 7 6 ϋ

 1H— NMR (CDC 13, δ ρ ρ m): 2.2 3 (q, 2 H), 2.83-2.29 (m, 2 H), 3.95 (s, 3 H), 4.09 — 4.20 (m, 1H), 7.12 (d, 2H), 7.28 (d, 2H) Example 4

 β-(5-chloro-1-1-methyl-1-trifluoromethylpyrazole-4-yl)-a-1 [2-(4-chloro-phenyl) ethyl] 1-vivaloyloxyacrylonitrile (Compound No. 4 — 2, 4-3)

Dissolve 9.28 g of a- (5-Chloro-1-methyl-3-trifluoromethylvirazol-1-yl) carbonylyl- _γ- (4-chlorophenyl) ptyronitrile in THF 100 ml Then, under ice-cooling, 3.19 g of triethylamine and 3.82 g of bivaloyl chloride were sequentially added, followed by stirring at room temperature for 2 hours. The precipitated crystals were filtered, and the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/4) to give 7.76 g of the desired compound (4 — 2) and 0.05 g (4-3) were obtained, respectively. 4 — 2: Yield 6 9% Melting point 8 5 — 8 7 ° C

 4-1-3: Yield 0.4% Melting point 10 1 — 10 2 ° C ·

 1H-NM R (CDC 13, δ ppm): 1.20 (s, 9H), 2.61 (t, 2H), 2.89 (t, 2H), 3.93 (s, 3H), 7.14 (d, 2H), 7.29 (d, 2H) Example 5

 β- (5-Chloro-1-methyl-1-3-trifluoromethylpyrazole-4-yl) -β-Hydroxy-1-ct-1- (2-phenylethenyl) acrylonitrile (Compound No. 5—54) Manufacturing of

5-Methyl 1-methyl-3-trifluoromethylvirazole-4 Dissolve 0.8 g of rubonic acid in 10 ml of 'N, N-dimethylformamide, and add 0.5 g of carbonylbisimidazole. 7 g was added, and the mixture was stirred at room temperature for 1 hour. Next, 0.5 g of cinnamyl cyanide was added, and then 0.14 g of sodium hydride (oil-based 60%) was added under ice cooling, followed by stirring at room temperature for 1 hour. Thereafter, 0.14 _g of sodium hydride (oil-based 60%) was added under ice-cooling, and the mixture was further stirred at room temperature for 3 hours. The reaction solution was poured into ice water, acidified with dilute hydrochloric acid, extracted with ethyl acetate, and the organic layer was concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane = 1-2) to obtain 0.9 lg of the desired compound. Yield 74%

1H-NMR (CDC 13, δ ppm): 3.95 (s, 3H), 6.20 (d, 1H), 6.90 (d, 1H), 7.12 -7.50 (m, 5H) Example 6

 β- (5-Chloro-1-methyl-1-3-trifluoromethylbirazol-4-yl) — a-(2—phenylenyl) 1 / 3—bivaloyoxylacrilonitrile (Compound No. 5— 1) Manufacture

β — (5-Chloro-1-methyl-1-3-trifluoromethylvirazole-41) — 0 -Hydroxy a- (2-phenylethenyl) acrylonitrile 0.91 g was dissolved in THF 10 ml, and triethylamine 0.3'2 g and bivaloyl chloride 0.40 g were dissolved under ice-cooling. Were sequentially added, and the mixture was stirred at room temperature for 2 hours. The precipitated crystals were filtered and the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (developing solvent; ethyl acetate _n- hexane = 1 Z4) to obtain 0.46 g of the desired compound . Yield 80% Melting point 80-82 ° C Example 7

 1-Methyl-1-3-trifluoromethyl-1- 4- [4- (4-fluorophenyl) 4-oxo-2-cyanobutyryl] — Preparation of 5-chlorobirazol.

1-methyl-3-trifluoromethyl-14-cyanoacetyl-5-chloropyrazole 1.0 g, diisopropylethylamine 1.0 g, methylene chloride 10 m 4 1.3 g of 1-oxo-2-promoethyl) Fluorobenzene was added at 0 g. After reacting at room temperature for 18 hours, the reaction solution was poured into ice water and extracted with ethyl acetate. After the extract was washed with water and dried over magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was subjected to column chromatography (silica gel, n-hexane / ethyl acetate == 1: 1), and had a melting point of 179-181. 1-methyl-3-trifluoromethyl-4-[4-(4 (1-Fluorophenyl) 1-4-oxo-1 2-cyanobutyryl] — 5-chloro-opening 1.0 g of virazole was obtained. Example 8

 1 chill-3-trifluo. Production of methyl-4- [4- (4-fluoro-7-yl) -4-ethoxyethoxymino-2-cyanov * tyryl] -5-chloride, pentayl (Compound No. 8-65)

"3

1-Methyl-3-trifluorodimethyl-4-cyanoacetyl-5-octane DQl: 'Lazo'-1.0 g, potassium carbonate 1.1 g, sodium iodide 0.6 g and 7 set :: tolyl 10 ml mixture To 70% pure 4- (1-i-toximinino-2-phenyl- £ 3 moethyl) fluo D was added 1.5 g of benzene at 0 ° C. After reacting at room temperature for 18 hours, the reaction solution was poured into ice water and extracted with I-yl acetate. After the extract was washed with water and dried over magnesium sulfate, the solvent was distilled off under reduced pressure. The obtained residue is subjected to column chromatography (silica gel, η-hexane / ethyl acetate = 1/1), and has a melting point of 73 to 75 ° C. 1-methyl-3-trifluoro-!! yl-4- [4- (4-FluoroQinyl) -4-1toximinino-2-cyanof * tyryl] -5-chlorophyll, factory 1.2 was obtained. Example 9

 Tomethyl-3-trifluoro U-methyl-4- [4- (4-trifluoro-D-Finyl) -4-ethoxyimino-2-cyanov * tyryl] -5-phenol 8— 7 3) Synthesis

1-Methyl-3-triflurescent D-Methyl-4-cyanoacetyl-5-gulyl 7.5g, potassium carbonate 8.2g, sodium trichloride 5.4g and acetonitrile 225ml in a mixture of 86% pure 4_ (1 -Ethoxyimino-2-F * D-moethyl)-α, a, α-trifur; 12.6 g of tn toluene was added at -5 ° C. After reacting at room temperature for 19 hours, the reaction solution was poured into ice water and washed with n-hexane. The pH of the aqueous layer was adjusted to 1 by adding concentrated hydrochloric acid, and then extracted with I-acetic acid. The extract is washed with water and dried over magnesium sulfate, the solvent is distilled off under reduced pressure, and the residue obtained is washed with n-hexane and has a melting point of 77 to 80 ° C; There was obtained 9.9 g of 3-trifluoronutyl_4- [4- (4- (trifluoro-1-phenyl) -4-yl) -4-ethoxyimino-2-cyanofu'tyryl] -5-chlorophenol.

Example 10

 Production of 1-methyl-3-trifluoro D-methyl-4- [4- (4-trifluoro U-F I :: l) -4-oxo-2-cyanov * tyryl] -5-chlorohydra

1-Cyl-3-trifluoromethyl-4-cyanoacetyl-5-chlorophenol. 2 g of razor'-le, 1.23 g of ilamine's thiiramine and chloramine; 91.6% purity in a mixture of 40 ml of styrene, 4- (1-oxo-2-phenyl Πmoethyl) -α , a, α-Trifluorotoluene 2.55g Added at 0 ° C. After reacting at room temperature for 18 hours, the reaction solution was poured into ice water and extracted with I-chloroacetic acid. After the extract was washed with water and dried with magnesium sulfate, the solvent was distilled off under reduced pressure. The obtained residue was subjected to column chromatography ♦ raffy (silica gel, n-hexane / I-yl acetate = 4) to give 1-methyl-3-trifluoromethyl-4- [4- (4-trifluorophenyl)- 4-year-old 2-cyanofu * tyryl] -5-chlorohydrosol-2.4 g was obtained.

Ή NMR (CDCL ₃ ): δ 3.52 (q, 1H), 4.02 (s, 3H), 4.14 (q, 1H), 4.95 (q, ΙΗ), 7.78 (d, 2Η), 8.08 (d, 2H) ),

Example 1 1

 Production of 1-methyl-3-trifluoro D-methyl-4- (2-phenyl-2-cyanoacetyl) -5-phenol

1-;! 7.0 g of bromine was added dropwise at room temperature to a mixed solution of 5.0 g of chill-3-trifluoromethyl-4-cyanoacetyl-5-chlorophenol and 30 ml of chloroform. After reacting at room temperature for 3 hours, the reaction solution was washed with saturated aqueous sodium hydrogen carbonate and dried over magnesium sulfate. The residue obtained by evaporating the solvent under reduced pressure was subjected to column chromatography (silica gel, η-hexane / I-yl acetate = 2/1), and 1-methyl-3 having a melting point of 76 to 77 ° C was used. 5.3 g of -trifluo (chill-4- (2-phenyl-2-D-cyanoacetyl) -5-chlorohyrazol-) was obtained.

 Example 1 2

 1-Cyl-3-trifluoromethyl-4- (2-chloro-2-cyanoacetyl) _ 5-chloro

1 tyl-3-trifluoro D-methyl-4-cyanoacetyl-5-chlorophenol, 2.0 g of sodium chloride, N-dimethyl imidene (abbreviated as NCS) 2.1 g, 20 ml of methylene chloride Reflux for 3 hours. The reaction solution cooled to room temperature was washed with water and dried with magnesium sulfate. The residue obtained by evaporating the solvent under reduced pressure was subjected to column chromatography (silica gel, η-hexane / I-yl acetate = 2/1) to give 1-tyl-3-fluoro-pentyl-4- (2 Thus, 0.5 g of -chloro-2- (7-acetyl) -5-phenol was obtained.

! H NMR (CDCL ₃ ): δ 4.02 (bs, 4 H) Tables 4 to 10 show typical examples of the compounds of the present invention thus produced. Table 1 shows the 1 H-NMR data. Table 4

* []: Melting point ° c, a certain number n _D : Refractive index. same as below. a: Either isomer. Others are mixtures of isomers.

71 Replacement form (Rule 26)

Table 4 (continued)

73 Replacement Form (Rule 26) Table 4 (continued)

74 Replacement form (Rule 26) Table 5

Compound

 B R Y Xa Physical constant * Number

 5-1 b25 r6 Ph H [80-82]

5-2 bl r6 Ph H Viscous oil a

5-3 bl r6 Ph H Viscous oil a

5-4 b25 r6 4-Cl-Ph H [125-128] a

5-5 b25 r6 4-Cl-Ph H [169-170] a

5-6 b25 r22 4-Cl-Ph H [187-189] a

5-7 b25 r22 4-Cl-Ph H [127-129] a

5-8 b25 r6 4-Cl-Ph Me n _D ²⁶⁷ 1.4819

5-9 b25 r22 4-Cl-Ph Me n _D ²⁷⁷ 1.5082

5-10 b25 r6 2,6-Cl ₂ -Ph Me n _D ²⁷⁵ 1.4506

5-11 b25 r6 4-tBu-Ph H [74-76]

5-12 b25 r22 4-tBu-Ph H [90-92] a

5-13 b25 r22 4-tBu-Ph H [149-151] a

5-14 bl r22 Ph H [69-71]

5-15 b25 r6 4-CF ₃ -Ph H [108-lll] a

5-16 b25 r6 4-CF ₃ -Ph H [165-167] a

5-17 b25 .r22 4-CF ₃ -Ph H [186-187]

5-18 b25 r6 4-F-Ph H [79-83] a

5-19 b25 r6 4-F-Ph H [149-152] a

5-20 b25 r22 4-F-Ph H [150-169]

5-21 b25 r6 Ph Et n _D ²²⁶ 1.5315

5-22 b25 r6 Ph nPr [73-74] a

5-23 b25 r6 Ph nPr n _D ²³⁰ 1.5203 a

5-24 b25 r6 Ph nHex n _D ²²⁶ 1.4998

5-25 bl r6 4-tBu-Ph H n _D ²²⁶ 1.5305

5-26 bl r22 4-tBu-Ph H n _D ²²⁶ 1.5878

5-27 b25 r6 4-Me-Ph H [125-126] a

5-28 b25 r6 4-Me-Ph H [198-199] a

5-29 b25 r22 4-Me-Ph H [112-113] a Table 5 (continued)

76

(Rule 26) Table 5 (continued)

77 Replacement form (Rule 26)

Table 7

 79

Replacement form (Rule 26) Table 7 (continued)

80

Rules) Table 8

 81

ぇ 闬 Paper (Rule 26) Table 8 (continued)

82 Replacement Form (Rule 26) Table 8 (continued)

83

Replacement form (Rule 26) Table 8 (continued)

84 Replacement form (Rule 26)

Compound R v person 5

 Number

9-1 b25 r6 4-F-Ph Et n D 20 - 6 1.5054

9-2 b25 r23 4-F-Ph Et n _D ²⁰⁶ 1.5273

9-3 b25 r6 4-F-Ph nPr n _D ²³⁹ 1.4945

9-4 b25 r23 4-F-Ph nPr n _D ^{23 9} 1.5 100

9-5 b25 r6 4-F-Ph iPr n _D ^{20 5} 1.5004

9-6 b25 r23 4-F-Ph iPr n _D ^2a5 1.5231

9-7 b25 r6 4-CF ₃ -Ph Et n _D ^{26 8} 1.4346

9-8 b25 r22 4-CF ₃ -Ph Et n _D ^{26 0} 1.5387

9-9 b25 r23 4-CF ₃ -Ph Et n _D ^{27 6} 1.4168

9-10 b25 r6 4-CF3-PI1 nPr n _D ^{27 2} 1.4187

9-11 b25 r22 4-CF3-PI1 nPr n _D ^{22 4} 1.5076a

9-12 b25 r22 4-CFg-Ph nPr n _D ^{22 4} 1.5020a

9-13 b25 r6 4-CF3-PI1 iPr n _D ^{26 0} 1.4440

9-14 b25 r22 4-CFg-Ph iPr n _D ²⁶ 1.4743

9-15 b25 r6 tBu Et n _D ^{23 7} 1.4717

9-16 b25 r23 tBu .. Et n _D ^{22 8} 1.4918

9-17 b25 H 4-F-Ph Et Viscous oil

9-18 b25 H 4-F-Ph nPr Viscous oil

9-19 b25 H 4-F-Ph iPr Viscous oil

9-20 b25 H 4-CFg-Ph Et Viscous oil

9-21 b25 H 4-CF3-PI1 nPr Viscous oil

9-22 b25 H 4-CF3-PI1 iPr Viscous oil

9-23 b25 H tBu Et Viscous oil

85 Paper (Rule 26)

86 26 Table 10 (continued)

Table 10 (continued)

88

Replacement form (Rule 26) / vu O sz-ooofcldAV;

Narrow

Next, some examples of the composition of the present invention will be described. However, the additives and the addition ratio are not limited to these examples, and can be changed in a wide range. Parts in Formulation Examples indicate parts by weight. Example 13 wettable powder

 Compound of the present invention 40 parts

 Diatomaceous earth 5 3 parts

 Higher alcohol sulfate 4 parts

 Alkyl naphthalene sulfonate 3 parts

If the above are uniformly mixed and finely pulverized, a wettable powder with an active ingredient of 40% is obtained. Example 14 Emulsion

 Compound of the present invention 30 parts

 Xylene 3 3 parts

 Dimethylformamide 30 parts

 Polyoxyethylene alkylaryl ether

 7 copies

By mixing and dissolving the above, an emulsion containing 30% of the active ingredient is obtained. Example 15 Dust

 Compound of the present invention 10 parts

 Talc 8 9 parts

 Polyoxetylene alkylaryl ether

 1 copy

If the above are uniformly mixed and finely pulverized, a powder containing 10% of the active ingredient is obtained. Example 16 granules

 5 parts of the compound of the present invention

 Clay 7 3 parts

 Bentonite 20 parts

 Dioctyl sulfosuccinate sodium salt

 1 copy

 1 part of sodium phosphate

The above is well pulverized and mixed, water is added and the mixture is kneaded well, and then granulated and dried to obtain granules having an active ingredient of 5%. Example 17 Suspension

 Compound of the present invention 10 parts

 Sodium ligninsulfonate 4 parts

 1 part of sodium dodecylbenzenesulfonate

 Xanthan gum 0.2 parts

 Water 84.8 parts

 If the above components are mixed and wet-pulverized to a particle size of 1 micron or less, a suspension containing 10% of the active ingredient is obtained. Industrial applicability:

 Examples in which the composition of the present invention obtained as described above is applied as a pest control agent are shown below.

(Test Example 1) Efficacy against Namihadaji

 15 to 10 days after germination of the seeds sown in a three-dimensional bowl, 15 inoculated female adults of Nami-Nada two, which are resistant to organic phosphorus, were administered. According to the wettable powder formulation shown in Example 7, a chemical solution diluted with water was sprayed so that the compound concentration was 125 ppm. They were placed in a thermostatic chamber at a temperature of 25 t; and a humidity of 65%, and three days after spraying, the adulticidal rate was examined. The test is a .2 iteration. In addition, chlordimeform was used as a control compound. The insecticidal rate of the control compound (125 ppm) was 13%.

 As a result of the test, the following compounds showed an insecticidal rate of 100% after 3 days. The compound numbers correspond to the numbers in Tables 4 to 9 above. Compound number:

4-1, 4-1 2, 4-3 4-5, 4-6, 4-7, 4-8, 4-9 4-1 1, 4 1 1 2 4-14 16, 4-17, 4-18, 4-19 4-21, 4-22 4-24, 4-25 4-26, 4-27, 4-29, 4-3 0 4-3 1, 4-3 2 4-3 3,-3 4-3 5, 4-3 6, 4-3 7, 4-3 8 4-3 9, 4-4 0 4- 4 1, 4-4 2 4-4 3, 4-44, 4 1 4 5, 4-4 6 4-4 7, 4-4 8 4-4 9,-5 0 4-5 1, 4-5 2, 4, 5-3, 4-5 6 4-59, 4-6 0 4-61, 4-62 4-70, 4-71, 4-72, 4-73, 4- 7 4, 4-7 5 4-7 6, 4-7 7 4-7 8, 4 1 7 9, 4-8 0, 4-8 1 4-8 2, 4 — 8 4 4-8 5, 4 — 8 9 4-9 0, 4-9 1, 4-9 2, 4-9 3 4-9 6, 5 1 1 5 1 2, 5-3, 5 — 4, 5 — 5, 5 — 6, 5—7, 5—8 5—9, 5— 1 1, 5-1 2, 5-13, 5-14, 5-15, 5 8, 5-1 19, 5-2 0 5-

2 4, 5-2 7, 5-29, 5-3 1, 5-3 3, 5-3 4, 5-3 5, 5-3 6 5 1

3 7, 5-38, 5-39, 5-40, 5-41, 51-42, 5-45, 5-48

 6 1 9, 6-10, 6-1 1, 6-1 2, 6-16, 6 7, 6 1 18, 6 1

 6-20, 6-21, 6-24,

 7 1 2, 7 — 4, 7 — 6, 7 — 8, 7 — 1 1, 7 1 1 2, 7-1 3, 7-1,, 7-

1 5, 7 — 16, 7-17, 7-18, 7 — 19, 7-20, 7-23, 7-2 6. '7-2 7, 7-2 8, 7 -2 9, 7-3 0, 7-3 1, 7-1 3, 4-7-3 5, 7-3 6

 8-1, 8-2, 8-3, 8-4, 8-5, 8-6, 8-7, 8-1, 8-9, 8-1 8-1 2, 8-13, 8 -18-1 5, 8-1 6 8-1 7, 8-1 8, 8-1

9, 8-2 0 8-2 1 8-2 2 8-2 3, 8 1 2 4 8-2 5, 8-2 6, 8-2 7, 8-2 8 8-2 9 8-3 0 8-3 1, 8-3 2 8-3 3, 8-1 3 4, 8-3 5, 8-3 6 8-3 7 8-3 8 8-3 9, 8-4 0 8 1 1, 8 -4 2, 8-4

3, 8-4 8-4 5 8-4 6 8-47, 8-1 4 8 8-49, 8-1 50, 8-51, 8-5 2 8-5 3 8-5 4 8 -5 5, 8-5 6 8-5 7, 8-5 8, 8-6

4, 8-6 5 8-7 0 8-7 3 8-7 6, 8-7 7 8-7 8, 8-7 9, 8-80, 8-9 2 8-9 3 8-9 4 8-9 5, 8-1 9 6 8-9 7

 1 1, 9 1 2, 9 1 3, 9-4 9-5, 9-6, 9 7, 9-8, 9-9, 9-1

0, 9-1 1, 9-1 2, 9-1 3 9-1 4, 9-1 5 9 1 16

(Test Example 2) Efficacy against Citrus Red Mite

 After inoculating 10 adult females of the mandarin red mite on the leaves of tangerines placed in a petri dish, dilute with water so that the compound concentration becomes 125 ppm according to the formulation of the emulsion described in Example 8 of the above-mentioned drug. The diluted drug was sprayed on a rotary spray tower. The plants were placed in a constant temperature room at a temperature of 25 and a humidity of 65%, and the insecticidal rate was examined 3 days after spraying. The test is in duplicate. Chlordimethylform was used as a control compound. The insecticidal rate of the control compound (125 ppm) was 50%.

 As a result of the test, the following compounds showed an insecticidal rate of 100% after 3 days. The compound numbers correspond to the numbers in Tables 4 to 10. Compound number:

 4-1,-2, 4-3, 4-5, 4-6, 4-7, 4-1 8, 4-9, 4-1 1, 4-1 2, 4-1 4, 4-15 , 4-1 6, 4-1 7, 4-1 8, 4-1 9, 4-2 1,

-25, 4-26, 4-29, 4-30, 4-31, 4-32, 4-33, 4-34, 4

-3 7, 4-3 8, 4-1 3 9, 4-4 0, 4-4 1, 4-1 4 2, 4-4 3, 4-4 4, 4

-4 5, 4-46, 4-47, 4-48, 4-49, 4-50, 4-53, 4-59, 4 1 6 4 1 6 1, 4-6 2, 4-7 2, 4-7 3 1 7 4, 4-1 7 5, 4-7 6 4 1 7 4-1 7 8, 4-8 2, 4-1 8 4, 4-8 9 1 9 0, 4-9 1, 4-9 2 4-9

 5-1, 5-2, 5-3, 5-4 5-5, 5-5-1, 8, 5-9.5 1-1 5

2, 5-1 3, 5-1, 5-1 5 5-1 6 1 1 8, 5-1 9 5-2 0 5 1 2 2, 5-2 3, 5-2 4, 5-2 7 5-2 8 1 2 9, 5-3 0 5 1 3 1 5 1 3 2, 5-3 3, 5-3 4.5-3 5 5-3 6-3 7, 5-3 8 5-3 9 5 1 4 0, 5-4 1, 5-4 2, 5-3 5-4 4-5

 6 one 4, 6—9.6-10, 6—1 16-1 2-16, 6-17, 6-18 1 19, 6-20, 6-21, 6- twenty four

 7-1, 7-2, 7-7 7-8, 7-9, 7-1 0,, 7-1 1 2, 7-1

1 4 7-15, 7-16, 7-17, 7-20, 7-2 6.7-27, 7-28, 7 1 2 9 7-3 0, 7-3 1 , 7 — 3 4, 7 — 3 5, 7 1 3 6

 8 1, 8-2, 8-3, 8-4, 8-5, 8-6, 8-7, 8-8, 8-9,-1

8-1 1 8-1 2 8-1 3 8-1 4-15, 8-16 '8-1 7, 1 1

8, 8-1 9 8-2 0 8-2 1 8-2 2-23, 8-24, 8-25, 1 26, 8-27 8-2 8 8-2 9 8- 3 0-3 8-3 2, 8-3 3, 1 3 4, 8-3 5 8-3 6 8-3 7 8-3 8 1 3 9, 8-40, 8-4 1, 1 4 2, 8-4 3 8-4 8-4 5 8-4 6 1 47, 8-48, 8-49, 1 50, 8-5 18-5 2 8-5 3 8-5 4 1 5 5, 8-5 6 '8-5 7, 1 5

8, 8-6 4 8-6 5 8-7 0 8-7 3 1 7 6, 8-7 7, 8-7 8, 1 7

9, 8-8 0 8-9 2 8-9 3 8-9 4

 -1, 9-2, 9-3, 9-4 9-5, 9-6, 9-7, 9-8, 9-9, 9-9-1 1, 9-1 2, 9-13 9-14, 95, 9-16

 0-2, 1 0-9

(Test Example 3) Efficacy test for P. aphid

 After 10 days of germination, seedlings sown in three-size pots were inoculated with adult Aphid aphids. One day later, adults were removed to obtain cucumber parasitized by the produced nymphs. According to the emulsion formulation shown in Example 8, a drug diluted with water so that the compound concentration was 125 ppm was sprayed on the cucumber. The plants were placed in a constant temperature room at a temperature of 25 ° C and a humidity of 65%, and after 5 days, the insecticidal rate of Aphid aphid was investigated. The test was performed in duplicate.

As a result, the following compounds showed an insecticidal rate of 100%. The compound numbers correspond to the compound numbers in Tables 5, 6, and 8 described above. Pirimicarp was used as a control compound. The insecticidal rate of the control compound was 9%. Compound number:

 5—10, 5—24, 5—40,

 6—4, 6—5, 6—6, 6—7, 67, 6—18, 6—19, 6—20, 6—2

1,

 8-1, 8-2, 8-3 8-4, 8-5, 8-6, 8-7, 8-8, 8-1 2, 8

1 3, 8—1 4, 8-1 5 8—1 6, 8—1 8, 8—1 9, 8-2 1, 8—2 2, 8

2 3, 8-24, 8-25 8-26, 8-27, 8-28, 8-29, 8-30, 8

3 1, 8-3 2, 8-3 3 8-3 4, 8-35, 8-36, 8-44, 8-45, 8

4 6, 8-4 7, 8-4 8 8-49, 8-50, 8-51, 8-52, 8-53, 8

5 4, 8-5 5, 8-5 6 8-5 7, 8-58, 8-76, 8-77, 8-78, 8

7 9, 8-8 0, 8-9 7

Claims

The scope of the claims

 1. General formula [I]

Wherein A is a group represented by the following formulas A 1, A 2, A 3, A 4, A 5, A 6, A 7, A 8, A 9, AA 11 and A 12 Represents one selected from the group.

 A

 A1 A2 A3 A4

 Α5 Α6 Α7

 Α8 Α9 Α10

 Α11

(X physician chi _2, chi ₃ and chi ₄ are each independently a hydrogen atom, a halogen atom, a ₆ Al kill group or _haloalkyl group, X ₅ is a hydrogen atom, - ₆ alkyl group, C _{2 6} alkenyl, C _{2 6} Haroaruke two group or an optionally substituted Hue sulfonyl 〇 i ₆ alkyl group,

x ₆ and x ₇ each independently represent a cis-s alkyl group, and x ₆ and x ₇ may together form a 5- to 8-membered ring.

Y is Shiano group, C _{3 6} alkyl group, C ₃ _ ₆ cycloalkyl group, in substituted with optionally phenyl C ^ -s alkyl group, in an optionally substituted phenyl group, in optionally substituted phenoxy group, in optionally substituted phenoxy C t_ ₆ alkyl group which may be substituted by G _t-phenylene group, a heteroarylthio group, which may be substituted by G _t-phenylene thioether C ₆ alkyl group, in which may be substituted Hue Nils sulfinyl group which may be substituted by Gi Fuenirusurufu Iniru - ₆ alkyl group, which may phenylalanine sulfonyl be-substituted with G i group may phenylalanine alkylsulfonyl optionally substituted by a G _t 0 i ₆ alkyl group, in optionally substituted Aniri amino group, in optionally substituted Aniri Bruno C, _ ₆ alkyl group, in an optionally substituted thienyl group, in optionally substituted thienyl C i ₆ alkyl group, G in, Optionally substituted pyridyl And represents one group selected from the group consisting of a pyridyl Ci- ₆ alkyl group which may be substituted with and.

Z represents an oxygen atom, a sulfur atom, or a hydrogen atom or a nitrogen atom substituted by a C ₆ alkyl group.

Is nitro group, Shiano group, a halogen atom, C ^ e alkyl, C ₂ _ ₆ alkenyl, C _{2 6} alkynyl group, C ₃ _ ₈ cycloalkyl group, C i ₆ haloalkyl group, C ₂ Nono Roarukeniru group, C i-s alkoxy group, - ₆ haloalkoxy group, C _{2 6} alkenyl Okishi group, C _{2 6} haloalkenyloxy O alkoxy group, C _{2 6} Arukiniruokishi group, C ₁ - ₆ Al Kiruchio group, C ^ ₆ alkyl sul Fier, C! _ _Fi alkylsulfonyl group, C i ₆ § alkylamino group, di 〇 ₁ - ₆ alkylamino amino group, Application Benefits C i ₆ alkylsilyl, C i-e § alkoxy ₍₁ - ₆ alkyl group, - ₆ alkylthio C i-e Alkyl group, C i—s alkylsulfinyl — ₆ alkyl group, — ₆ alkylsulfonyl ホ i ₆ alkyl group, C

! _ ₆ alkylcarbonyl group, - ₆ alkoxycarbonyl group, phenyl optionally substituted with G ₂ C i-e alkyl group, optionally substituted with G ₂ Hue sulfonyl 0 i-6 alkoxy group, with G ₃ An optionally substituted phenyl group, an optionally substituted pyridyl group with G ₂ , an optionally substituted pyridyloxy group with G ₂ , an optionally substituted phenyl group with G ₄ , and an optionally substituted phenyl group with G ₄ Represents an enoxy group.

G ₂ represents a C i -e alkyl group, a halogen atom, a noroalkyl group, or a C i -no alkoxy group.

G ₃ represents a C alkyl group or a halogen atom.

G ₄ are nitro group, Shiano group, a halogen atom, C ₆ alkyl group, - ₆ Haroaruki group, alkoxy group, C i-e haloalkoxy group, - ₆ alkylthio group, _ ₆ alkylsulfinyl group, C -! ₆ alkylsulfonyl group, C -! ₆ alkylamino amino group, di-alkylamino groups, - ₆ alkylcarbonyl group, - represents a ₆ alkoxy force Lupo two Le group. )

 B represents a phenyl group substituted with W or a heterocyclic group substituted with W.

Here, W is a nitro group, Shiano group, a halogen atom, - ₆ alkyl group, C _{3 8} cyclo alkyl group, _haloalkyl group, C i ₆ alkoxy group, - ₆ Haroarukoki sheet group, C _i-6 alkylthio Group, C -s alkylsulfinyl group, — ₆ alkylsulfonyl group, C i-e alkylamino group, di C i-e alkylamino group, — 6 alkyl group, luponyl group, ₆ alkoxycarbonyl group, substituted with G ₅ which may be phenyl group, optionally substituted by G ₅ represents an phenoxy group,

G ₅ is a nitro group, Shiano group, a halogen atom, _alkyl group, C ₁ _ ₆ Haroaruki Le group, - _fi alkoxy group, Nono Roarukokishi group, ₆ alkylthio group, _ ₆ alkyl sulfide El group, C i ₆ alkyl represents 6 alkylcarbonyl group, a C i_ ₆ alkoxy force Lupo two group, - a sulfonyl group, C i-e alkylamino amino group, di 〇 ₁ - ₆ alkylamino amino group,

 The heterocyclic group substituted with w is a triazolyl group, thiazolyl group, oxazolyl group, isooxazolyl group, isothiazolyl group, pyrazolyl group, imidazolyl group, tetrazolyl group, oxaziazolyl group, thiadiazolyl group, chenyl group, furyl group, It is a group selected from the group consisting of a pyrrolyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, and a birazinyl group.

R is a hydrogen atom, an alkyl group, a group represented by the formula CO Rt, a group represented by the formula CS Ri, a group represented by S 0 ₂ R ₂ , C i — e alkyl carbonyldioxy ₆ i alkyl group, a C ₃ _ ₆ cycloalkyl carbonyl O carboxymethyl C E ₆ alkyl group or an optionally substituted full E sulfonyl carbonyl O carboxymethyl C _fi alkyl group.

(Wherein, Ri is - _{1 2} alkyl group, C _{3 6} cycloalkyl group, - ₆ Haroaruki le group, C -! ₆ alkoxy group, C ^ - s alkylthio group, C ie alkylamino amino group, di C

! _ ₆ alkylamino group, phenyl which may have a substituent <i ₆ alkyl group, phenyl which may have a substituent C! _ ₆ phenyl which may have an alkoxy group or a substituent Le group was Table, R ₂ represents - _{1 2} alkyl group or an optionally substituted phenylene Le group. )

However, B is a phenyl group substituted with W or a pyridyl group substituted with W, and R is a hydrogen atom, a ₆ alkyl group, a group represented by the formula COR !, a group represented by the formula CSR! In the case of a group represented by S 0 ₂ R ₂ , A is not a benzyl group substituted with ] The compound represented by these.

2. — General formula (3)

(Wherein A represents the same meaning as in claim 1) and a compound represented by the general formula (4)

0

 L 义 (4)

(Wherein B has the same meaning as in claim 1 and L represents a leaving group.) A compound represented by the formula (2):

0

(2)

 CN

(In the formula, A and B represent the same meaning as described above.)

 3. General formula (5)

(Wherein B has the same meaning as in claim 1) and a compound represented by the general formula (6):

 A- L

 (Wherein, A and L have the same meanings as in claim 2), wherein a compound represented by the following formula is reacted:

(In the formula, A and B represent the same meaning as described above.)

4. General formula (I)

(Wherein, A, B and R have the same meanings as in claim 1.)

An insecticide and acaricide, comprising a compound represented by the formula or a salt thereof as an active ingredient.