CN101652354B

CN101652354B - Insecticidal aryl isoxazoline derivatives

Info

Publication number: CN101652354B
Application number: CN200880011571.8A
Authority: CN
Inventors: 三原纯; 村田哲也; 山崎大锐; 米田靖; 涉谷克彦; 下城英一; U·戈基恩斯; A·特伯格; T·巴赫
Original assignee: Bayer CropScience AG
Current assignee: Bayer Pharma AG
Priority date: 2007-04-10
Filing date: 2008-03-28
Publication date: 2014-06-18
Anticipated expiration: 2028-03-28
Also published as: JP2008260691A; CN101652354A

Abstract

The present invention relates to novel aryl isoxazoline derivatives having excellent insecticidal activity as insecticides and represented by the formula (I): and their use as insecticides and acarizides.

Description

Insecticidal aryl isoxazoline derivatives

The present invention relates to new aryl isoxazoline derivatives and the purposes as insecticide and miticide (acarizide) thereof.

The known pest control agent that can be used as of benzamide compounds that isoxazoline replaces, described in WO2005/085216.

For exploitation is as the more more broad spectrum new compound of effective active that has of sterilant, by research deeply and widely, contriver has now found that new aryl isoxazoline derivatives, it has more remarkable activity, wide spectrum have security more, in addition, it is also to obtaining the insect performance drug effect of the resistance to organophosphorus medicament and amino formate medicament.

The compounds of this invention is represented by following formula (I):

Wherein

A represents C or N;

R represents alkyl or haloalkyl;

X can be identical or different, and it represents Cl, Br, F, I, haloalkyl, nitro, alkyl, alkoxyl group, cyano group, halogenated alkoxy, alkyl sulphinyl, alkyl sulfenyl (alkylsulfenyl), alkyl sulphonyl, haloalkyl sulfinyl, haloalkyl sulfenyl, halogenated alkyl sulfonyl, amino, amido, alkoxycarbonyl amino, halogenated alkyl carbonyl amino, halo alkoxy carbonyl amino, alkyl sulfonyl-amino, halogenated alkyl sulfonyl amino, hydroxyl or sulfydryl;

Y can be identical or different, and it represents halogen, haloalkyl, nitro, alkyl, alkoxyl group, cyano group, halogenated alkoxy, alkyl sulphinyl, alkyl sulfenyl, alkyl sulphonyl, haloalkyl sulfinyl, haloalkyl sulfenyl, halogenated alkyl sulfonyl, hydroxyl, sulfydryl, amino, amido, alkoxycarbonyl amino, halogenated alkyl carbonyl amino, halo alkoxy carbonyl amino, alkyl sulfonyl-amino or halogenated alkyl sulfonyl amino; Or form an optional substituted ring together with the carbon atom that connects with them of two adjacent Y;

L represents 0,1,2,3,4 or 5;

M represents 0,1,2,3 or 4;

N represents 1,2 or 3;

R ¹and R ²represent independently of one another hydrogen, alkyl, optional substituted cycloalkyl, haloalkyl, cyano group, alkoxy carbonyl, alkenyl or alkynyl, or R ¹and R ²represent together C _2-5alkylidene group;

R ³represent hydrogen, alkyl, optional substituted cycloalkyl, haloalkyl, cyano group, thiazolinyl, alkynyl, alkyl-carbonyl or CH ₂-R ⁵, wherein R ⁵represent optional substituted phenyl or an optional substituted heterocyclic radical; And

R ⁴represent formyl radical, cyano group, alkyl-carbonyl, alkylthio carbonyl, halogenated alkyl carbonyl, halogenated alkylthio carbonyl, alkyl amino-carbonyl, alkylamino thiocarbonyl, dialkyl amino carbonyl, dialkyl amido thiocarbonyl, alkoxy amino carbonyl, alkoxyl group thiocarbonyl, alkoxy amino thiocarbonyl, alkoxy carbonyl, thio alkoxy carbonyl, thio alkoxy thiocarbonyl,

Alkyl sulphonyl or halogenated alkyl sulfonyl, wherein R ⁵definition as above; Or

R ³and R ⁴together with the nitrogen-atoms that can connect with them, form one 3 yuan to 6 rings, this ring also can contain 1 or 2 heteroatoms that is selected from N, O or S except N atom, and the carbon atom that wherein forms this ring can be replaced by ketone group or thioketones base.

In one embodiment, formula (I) compound is contained in the present invention, wherein

A represents C,

R represents haloalkyl,

R ³represent CH ₂-R ⁵, wherein R ⁵represent optional substituted phenyl or an optional substituted heterocyclic radical that is selected from following group: furyl, thienyl, pyrryl, isoxazolyl, pyrazolyl, oxazolyl, Evil thiazolyl (oxathiazolyl), imidazolyl, triazolyl, oxadiazolyl, thiadiazolyl group, tetrazyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, indyl, benzoxazolyl, quinolyl; And

X, Y, l, m, n, R ¹, R ², R ⁴as defined above, or as defined herein institute defines preferably or in one of particularly preferred embodiment.

In another embodiment, formula (I) compound is contained in the present invention, wherein

A represents C,

R represents haloalkyl,

L represents 3,

X, Y, l, m, n, R ¹, R ², R ³, R ⁴as defined above, or as defined herein preferably or in one of particularly preferred embodiment institute define, condition is:

(1) in the time that two X are identical and represent F, Cl or Br, if the 3rd X is at 4-position bonding, do not represent F, CH ₃, CF ₃, OH, NH ₂, NO ₂, CN, OCH ₃, OCH ₂cH ₃, O-n-propyl, O-CHF ₂or OCF ₃,

Or (2) work as R ⁴while representing another substituting group except methyl carbonyl, if X, at 5-position bonding, does not represent CF ₃,

Or (3) are in the time that the X of a 5-position represents that the X of Br and another 3-position represents F or Cl, do not represent OCH at the 3rd X of 4-position ₃.

In one embodiment of the present invention, each compound is represented by formula (Ia)

Wherein

A represents C or N, and it all can be substituted separately base Y and replace;

R represents alkyl or haloalkyl;

X can be identical or different, and it represents halogen, haloalkyl, nitro, alkyl, alkoxyl group, cyano group, halogenated alkoxy, alkyl sulphinyl, alkyl sulfenyl, alkyl sulphonyl, haloalkyl sulfinyl, haloalkyl sulfenyl, halogenated alkyl sulfonyl, amino, amido, alkoxycarbonyl amino, halogenated alkyl carbonyl amino, halo alkoxy carbonyl amino, alkyl sulfonyl-amino, halogenated alkyl sulfonyl amino, hydroxyl or sulfydryl;

Z or Y can be identical or different, and it represents halogen, haloalkyl, nitro, alkyl, alkoxyl group, cyano group, halogenated alkoxy, alkyl sulphinyl, alkyl sulfenyl, alkyl sulphonyl, haloalkyl sulfinyl, haloalkyl sulfenyl, halogenated alkyl sulfonyl, hydroxyl, sulfydryl, amino, amido, alkoxycarbonyl amino, halogenated alkyl carbonyl amino, halo alkoxy carbonyl amino, alkyl sulfonyl-amino or halogenated alkyl sulfonyl amino;

L represents 0,1,2,3,4 or 5;

M represents 0,1 or 2;

N represents 1,2 or 3;

P represents 0,1,2,3 or 4;

Formula (I) compound can obtain by the following stated preparation method (a) to (d).

Preparation method (a):

Prepare a method for the compounds of this invention, the method comprises the step that formula (II) compound reacts with formula (III) compound:

Wherein A, Y, m, n, R ¹, R ², R ³and R ⁴as above, and Hal represents halogen in definition,

Wherein R, X and l define as above.

Preparation method (b):

Prepare a method for the compounds of this invention, the method comprises the step that formula (IV) compound reacts with formula (V) compound:

Wherein A, R, X, l, Y, m, n, R ¹, R ²and R ³define as above,

R ⁴-L (V)

Wherein R ⁴define as above, and L represents halogen, alkylsulfonyloxy, aryl-sulfonyl oxygen or alkyl carbon acyloxy.

Preparation method (c)

Prepare a method for the compounds of this invention, the method comprises the step that formula (IV) compound reacts with formula (VII) compound:

Wherein A, R, X, l, Y, m, n, R ¹, R ²and R ⁴define as above,

R ³-L (VII)

Wherein R ³define as above, and L represents halogen, alkylsulfonyloxy, aryl-sulfonyl oxygen or alkyl carbon acyloxy.

Preparation method (d)

Prepare a method for the compounds of this invention, the method comprises the step that formula (VIII) compound reacts with formula (IX) compound:

Wherein A, R, X, l, Y, m, n and L define as above,

R ³-NH-R ⁴ (IX)

Wherein R ³and R ⁴definition as above.

According to the present invention, the aryl isoxazoline derivatives of above-mentioned formula (I) has and effectively kills insect and kill acarid activity.

Term used herein " alkyl " refers to the C of straight or branched _1-12alkyl, comprises for example ethyl, methyl, n-propyl or sec.-propyl, normal-butyl, isobutyl-, sec-butyl or the tertiary butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, positive decyl, n-undecane base and dodecyl, and preferably refers to C _1-6alkyl.In the group having as the alkyl of its molecular formula part, this moieties can have and above-mentioned " alkyl " described identical implication.Described alkyl can be unsubstituted or is replaced by least one suitable substituting group.

Term " amido " refers to for example alkyl-carbonyl-amino, cycloalkyl amino carbonyl and benzamido, and wherein moieties can have and above-mentioned " alkyl " described identical implication, and cycloalkyl moiety can have and following identical implication.Amido can be unsubstituted or is replaced by least one suitable substituting group.

Halogen part in term " halogen " and the group that replaced by halogen represents fluorine, chlorine, bromine and iodine.Preferred halogen is fluorine, chlorine and bromine.

Term " cycloalkyl " refers to C _3-8cycloalkyl, comprises for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, suberyl and ring octyl group, and preferably refers to C _3-7cycloalkyl.Described group of naphthene base can be unsubstituted or is replaced by least one suitable substituting group.

Term " thiazolinyl " refers to C _2-5thiazolinyl, comprises for example vinyl, allyl group, 1-propenyl, 1-(or 2-or 3-) butenyl and 1-pentenyl, and preferably refers to C _2-4thiazolinyl.Described thiazolinyl can be unsubstituted or is replaced by least one suitable substituting group.

" cyclic group " preferably refers to the ring that contains 3-6 carbon atom.This group is preferably aromatic ring, most preferably is phenyl ring.Described cyclic group can be unsubstituted or is replaced by least one suitable substituting group.

" heterocyclic radical " preferably refers to be selected from heteroatomic 5 yuan or the 6 yuan of heterocyclic radicals of N, O or S containing at least one, and described heterocyclic radical also refer to can be by benzo-fused annelated heterocycles base.Described heterocyclic radical can be unsubstituted or is replaced by least one suitable substituting group.

The specific examples of " heterocyclic radical " comprises furyl, thienyl, pyrryl, isoxazolyl, pyrazolyl, oxazolyl, Evil thiazolyl, imidazolyl, triazolyl, oxadiazolyl, thiadiazolyl group, tetrazyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, indyl, benzoxazolyl, quinolyl etc.

Suitable substituting group comprises for example following chemical group, amino, hydroxyl, halogen, nitro, cyano group, isocyano-, sulfydryl, isothiocyano, carboxyl, carboxamide (carbonamide), SF5, amino-sulfonyl, alkyl, cycloalkyl, thiazolinyl, cycloalkenyl group, alkynyl, monoalkyl-amino, dialkyl-7-amino, N-alkyloyl-amino, alkoxyl group, alkene oxygen base, alkynyloxy group, cycloalkyloxy, cyclenes oxygen base, alkoxyl group-carbonyl, alkene oxygen base-carbonyl, alkynyloxy group-carbonyl, aryloxycarbonyl, alkyloyl, thiazolinyl-carbonyl, alkynyl-carbonyl, aryl-carbonyl, alkylthio, cycloalkylthio, alkenylthio group, cyclenes sulfenyl, alkynes sulfenyl, alkyl sulfenyl, alkyl sulphinyl (comprising two kinds of enantiomeric forms of alkyl sulphinyl), alkyl sulphonyl, monoalkyl-amino-sulfonyl, dialkyl-7-amino alkylsulfonyl, alkylphosphine oxide base, alkylphosphines acyl group (comprising respectively two kinds of enantiomeric forms of alkylphosphine oxide base and alkylphosphines acyl group), N-alkyl-aminocarboxyl, N, N-dialkyl-7-amino carbonyl, N-alkyloyl-aminocarboxyl, N-alkyloyl-N-alkyl-aminocarboxyl, aryl, aryloxy, phenmethyl, benzyloxy, benzylthio-, arylthio, virtue is amino, benzyl amino, heterocyclic radical and trialkylsilkl.Also comprise further substituted substituting group, for example alkoxyalkyl, alkylthio alkyl, alkylthio alkoxyl group, alkoxyl group alkoxyl group, styroyl, benzyloxy, haloalkyl, halogenated alkoxy, halogenated alkylthio, haloalkane acyl group, halogenated alkyl carbonyl, halo alkoxy carbonyl, halogenated alkoxy alkoxyl group, halogenated alkoxy alkylthio, halogenated alkoxy alkyloyl, halogenated alkoxy alkyl.

In formula of the present invention (I) compound, preferably wherein each group as undefined compound

A represents C or N;

R represents C _1-6alkyl or C _1-6haloalkyl;

X can be identical or different, and it represents halogen, C _1-6haloalkyl, nitro, C _1-6alkyl, C _1-6alkoxyl group, cyano group, C _1-6halogenated alkoxy, C _1-6alkyl sulphinyl, C _1-6alkyl sulfenyl, C _1-6alkyl sulphonyl, C _1-6haloalkyl sulfinyl, C _1-6haloalkyl sulfenyl, C _1-6halogenated alkyl sulfonyl, amino, C _1-6alkyl-carbonyl, C _1-6alkoxycarbonyl amino, C _1-6halogenated alkyl carbonyl amino, C _1-6halo alkoxy carbonyl amino, C _1-6alkyl sulfonyl-amino, C _1-6halogenated alkyl sulfonyl amino, hydroxyl or sulfydryl;

Y can be identical or different, and it represents halogen, C _1-6haloalkyl, nitro, C _1-6alkyl, C _1-6alkoxyl group, cyano group, C _1-6halogenated alkoxy, C _1-6alkyl sulphinyl, C _1-6alkyl sulfenyl, C _1-6alkyl sulphonyl, C _1-6haloalkyl sulfinyl, C _1-6haloalkyl sulfenyl, C _1-6halogenated alkyl sulfonyl, hydroxyl, sulfydryl, amino, C _1-4alkyl-carbonyl-amino, benzoyl-amido, C _1-6alkoxycarbonyl amino, C _1-6halogenated alkyl carbonyl amino, C _1-6halo alkoxy carbonyl amino, C _1-6alkyl sulfonyl-amino or C _1-6halogenated alkyl sulfonyl amino;

L represents 0,1,2 or 3;

M represents 0,1 or 2;

N represents 1;

R ¹and R ²represent independently of one another hydrogen, C _1-6alkyl, optional substituted C _3-7cycloalkyl, C _1-6haloalkyl, cyano group, C _1-6alkoxy carbonyl, C _2-4thiazolinyl or C _2-4alkynyl, or R ¹and R ²represent together C _2-5alkylidene group;

R ³represent hydrogen, C _1-6alkyl, optional substituted C _3-7cycloalkyl, C _1-6haloalkyl, cyano group, C _2-4thiazolinyl, C _2-4alkynyl, C _1-6alkynyl carbonyl or CH ₂-R ⁵, wherein R ⁵represent optional substituted phenyl or an optional substituted heterocyclic radical; And

R ⁴represent formyl radical, cyano group, C _1-6alkyl-carbonyl, C _1-6alkylthio carbonyl, C _1-6halogenated alkyl carbonyl, C _1-6halogenated alkylthio carbonyl, C _1-6alkyl amino-carbonyl, C _1-6alkylamino thiocarbonyl, C _2-8(sum of carbon) dialkyl amino carbonyl, C _2-8(sum of carbon) dialkyl amido thiocarbonyl, C _1-6alkoxy amino carbonyl, C _1-6alkoxyl group thiocarbonyl, C _1-6alkoxy amino thiocarbonyl, C _1-6alkoxy carbonyl, sulfo--C _1-6alkoxy carbonyl, sulfo--C _1-6alkoxyl group thiocarbonyl,

C _1-6alkyl sulphonyl or C _1-6haloalkyl-alkylsulfonyl, wherein R ⁵definition as above; Or

R ³and R ⁴together with the nitrogen-atoms that can connect with them, form one 4 yuan or 5 rings, this ring also can contain 1 or 2 heteroatoms that is selected from N, O or S except N atom, and the carbon atom that wherein forms this ring can be replaced by ketone group or thioketones base.

In another preferred embodiment of the present invention, this compound is represented as undefined formula (Ia) by each group wherein

A representative can be substituted the C that base Y replaces;

R represents C _1-6alkyl or C _1-6haloalkyl;

X can be identical or different, and it represents halogen, C _1-6haloalkyl, nitro, C _1-6alkyl, C _1-6alkoxyl group, cyano group, C _1-6halogenated alkoxy, C _1-6alkyl sulphinyl, C _1-6alkyl sulfenyl, C _1-6alkyl sulphonyl, C _1-6haloalkyl-sulfinyl, C _1-6haloalkyl sulfenyl, C _1-6halogenated alkyl sulfonyl, amino, C _1-6alkyl-carbonyl, C _1-6alkoxycarbonyl amino, C _1-6halogenated alkyl carbonyl amino, C _1-6halo alkoxy carbonyl amino, C _1-6alkyl sulfonyl-amino, C _1-6haloalkyl-sulfuryl amino, hydroxyl or sulfydryl;

Z or Y, can be identical or different, and it represents halogen, C _1-6haloalkyl, nitro, C _1-6alkyl, C _1-6alkoxyl group, cyano group, C _1-6halogenated alkoxy, C _1-6alkyl sulphinyl, C _1-6alkyl sulfenyl, C _1-6alkyl sulphonyl, C _1-6haloalkyl sulfinyl, C _1-6haloalkyl sulfenyl, C _1-6halogenated alkyl sulfonyl, hydroxyl, sulfydryl, amino, C _1-4alkyl-carbonyl-amino, benzoyl-amido, C _1-6alkoxycarbonyl amino, C _1-6halogenated alkyl carbonyl amino, C _1-6halo alkoxy carbonyl amino, C _1-6alkyl sulfonyl-amino or C _1-6halogenated alkyl sulfonyl amino;

L represents 0,1,2 or 3;

M represents 0,1 or 2;

N represents 1;

P represents 0,1,2,3 or 4;

In another kind of preferred embodiment of the present invention, this compound is represented as undefined formula (Ia) by each group wherein

A representative can be substituted the N that base Y replaces;

R represents C _1-6alkyl or C _1-6haloalkyl;

L represents 0,1,2 or 3;

M represents 0,1 or 2;

N represents 1;

P represents 0,1,2,3 or 4;

In those formulas (I) compound, particularly preferably wherein each group as undefined compound

A represents C or N;

R represents C _1-4alkyl or C _1-4haloalkyl;

X can be identical or different, and it represents halogen, C _1-4haloalkyl, nitro, C _1-4alkyl, C _1-4alkoxyl group, cyano group, C _1-4halogenated alkoxy, C _1-4alkyl sulphinyl, C _1-4alkyl sulfenyl, C _1-4alkyl sulphonyl, C _1-4haloalkyl sulfinyl, C _1-4haloalkyl sulfenyl, C _1-4halogenated alkyl sulfonyl, amino, C _1-4alkyl-carbonyl, C _1-4alkoxycarbonyl amino, C _1-4halogenated alkyl carbonyl amino, C _1-4halo alkoxy carbonyl amino, C _1-4alkyl sulfonyl-amino, C _1-4halogenated alkyl sulfonyl amino, hydroxyl or sulfydryl;

Y can be identical or different, and it represents halogen, C _1-4haloalkyl, nitro, C _1-4alkyl, C _1-4alkoxyl group, cyano group, C _1-4halogenated alkoxy, C _1-4alkyl sulphinyl, C _1-4alkyl sulfenyl, C _1-4alkyl sulphonyl, C _1-4haloalkyl sulfinyl, C _1-4haloalkyl sulfenyl, C _1-4halogenated alkyl sulfonyl, hydroxyl, sulfydryl, amino, C _1-4alkyl-carbonyl-amino, benzoyl-amido, C _1-4alkoxycarbonyl amino, C _1-4halogenated alkyl carbonyl amino, C _1-4halo alkoxy carbonyl amino, C _1-4alkyl sulfonyl-amino or C _1-4halogenated alkyl sulfonyl amino;

L represents 0,1,2 or 3;

M represents 1;

N represents 1;

R ¹and R ²represent independently of one another hydrogen, C _1-4alkyl, optional substituted C _3-6cycloalkyl, C _1-4haloalkyl, cyano group, C _1-4alkoxy carbonyl, C _2-3thiazolinyl or C _2-3alkynyl, or R ¹and R ²represent together C _2-5alkylidene group;

R ³represent hydrogen, C _1-4alkyl, optional substituted C _3-6cycloalkyl, C _1-4haloalkyl, cyano group, C _2-3thiazolinyl, C _2-3alkynyl, C _1-4alkyl-carbonyl or CH ₂-R ⁵, wherein R ⁵represent optional substituted phenyl or an optional substituted heterocyclic radical; And

R ⁴represent formyl radical, cyano group, C _1-4alkyl-carbonyl, C _1-4alkylthio carbonyl, C _1-4halogenated alkyl carbonyl, C _1-4halogenated alkylthio carbonyl, C _1-4alkyl amino-carbonyl, C _1-4alkylamino thiocarbonyl, C _2-6(sum of carbon) dialkyl amino carbonyl, C _2-6(sum of carbon) dialkyl amido thiocarbonyl, C _1-4alkoxy amino carbonyl, C _1-4alkoxyl group thiocarbonyl, C _1-4alkoxy amino thiocarbonyl, C _1-4alkoxy carbonyl, sulfo--C _1-4alkoxy carbonyl, sulfo--C _1-4alkoxyl group thiocarbonyl,

C _1-4alkyl sulphonyl or C _1-4haloalkyl-alkylsulfonyl, wherein R ⁵definition as above; Or

R ³and R ⁴together with the nitrogen-atoms that can connect with them, form one 4 yuan or 5 rings, this ring also can contain 1 or 2 heteroatoms that is optionally selected from N, O or S except N atom, and the carbon atom that wherein forms this ring can be replaced by ketone group or thioketones base.

In another particularly preferred embodiment of the present invention, this compound is represented as undefined formula (Ia) by each group wherein

A representative can be substituted the C that base Y replaces;

R represents C _1-4alkyl or C _1-4haloalkyl;

Z or Y, can be identical or different, and it represents halogen, C _1-4haloalkyl, nitro, C _1-4alkyl, C _1-4alkoxyl group, cyano group, C _1-4halogenated alkoxy, C _1-4alkyl sulphinyl, C _1-4alkyl sulfenyl, C _1-4alkyl sulphonyl, C _1-4haloalkyl sulfinyl, C _1-4haloalkyl sulfenyl, C _1-4halogenated alkyl sulfonyl, hydroxyl, sulfydryl, amino, C _1-4alkyl-carbonyl-amino, benzoyl-amido, C _1-4alkoxycarbonyl amino, C _1-4halogenated alkyl carbonyl amino, C _1-4halo alkoxy carbonyl amino, C _1-4alkyl sulfonyl-amino or C _1-4halogenated alkyl sulfonyl amino;

L represents 0,1,2 or 3;

M is 0 or 1;

N is 1;

P represents 0,1 or 3;

In the equal preferred embodiment of one of the present invention, this compound is represented as undefined formula (I) by each group wherein

A represents C;

R represents CF ₃;

X can be identical or different, and it represents Cl, F, I, Br, CF ₃, NO ₂, C _1-4alkoxyl group, cyano group, C _1-4fluoroalkyloxy, C _1-4alkyl sulphonyl, amino, C _1-4alkyl-carbonyl, hydroxyl or sulfydryl;

Y can be identical or different, and it represents Cl, F, I, Br, CF ₃, NO ₂, C _1-4alkyl, C _1-4alkoxyl group, cyano group, C _1-4halogenated alkoxy, hydroxyl, amino;

L represents 1,2 or 3;

M represents 1;

N represents 1;

R ¹and R ²represent independently of one another hydrogen or C _1-4alkyl;

R ³represent hydrogen, C _1-4alkyl or CH ₂-R ⁵, wherein R ⁵represent optional substituted phenyl or an optional substituted heterocyclic radical, described heterocyclic radical is selected from furyl, thienyl, pyrryl, isoxazolyl, pyrazolyl, oxazolyl, Evil thiazolyl, imidazolyl, triazolyl, oxadiazolyl, thiadiazolyl group, tetrazyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, indyl, benzoxazolyl, quinolyl; And

R ⁴represent C _1-4alkyl-carbonyl, vinyl carbonyl, C _1-4alkylthio carbonyl, C _1-4halogenated alkyl carbonyl, C _1-4alkyl amino-carbonyl, two-(C ₁-C ₂) alkyl amino-carbonyl, C _1-4alkoxy amino carbonyl, C _1-4alkoxy carbonyl, sulfo--C _1-4alkoxy carbonyl, C _1-4alkyl sulphonyl ,-C (O) R ⁵, C (S) R ⁵, wherein R ⁵represent optional substituted phenyl or an optional substituted heterocyclic radical that is selected from following group: furyl, thienyl, pyrryl, isoxazolyl, pyrazolyl, oxazolyl, Evil thiazolyl, imidazolyl, triazolyl, oxadiazolyl, thiadiazolyl group, tetrazyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, indyl, benzoxazolyl, quinolyl.

In another kind of particularly preferred embodiment of the present invention, this compound is represented as undefined formula (Ia) by each group wherein

A representative can be substituted the N that base Y replaces;

R represents C _1-4alkyl or C _1-4haloalkyl;

L represents 0,1,2 or 3;

M is 0 or 1;

N is 1;

P represents 0,1 or 3

Another aspect of the present invention relates to so a kind of pharmaceutical composition, this pharmaceutical composition contains at least one the compounds of this invention, the preferably compound of one of at least one embodiment as defined herein, more preferably the compound of at least one preferred embodiment as defined herein, and the most preferably compound of at least one particularly preferred embodiment as defined herein, this pharmaceutical composition can be used for resisting zooparasite.

Formula (I) compound has asymmetric carbon, and thereby contains optically active isomer.In addition the polymorphic form that, the compounds of this invention can be different or as the mixture of different polymorphic forms and exist.The invention provides two kinds, pure polymorphic form and polymorphic form mixture, and it can be used according to the invention.

When using for example 4-(acetylamino methyl)-N-hydroxybenzene carboxylic imino-chlorine and the chloro-5-[1-of 1,3-bis-(trifluoromethyl) vinyl] benzene is during as raw material, and above-mentioned preparation method (a) can be represented by following reaction scheme.

When using for example 1-{4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] phenyl }-methylamine and Acetyl Chloride 98Min. are during as raw material, and above-mentioned preparation method (b) can be represented by following reaction scheme.

When using for example N-{4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] benzyl } ethanamide and methyl iodide are during as raw material, and above-mentioned preparation method (c) can be represented by following reaction scheme.

When using the bromo-4-of for example 3-[3-(brooethyl) phenyl]-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole and thioacetamide are during as raw material, and above-mentioned preparation method (d) can be represented by following reaction scheme.

Formula (II) compound that is used as raw material in preparation method (a) is new compound and can is reacted and obtain with a kind of halogenating agent by the compound being expressed from the next:

Wherein A, Y, m, n, R ¹, R ², R ³and R ⁴definition as above.

Many above-mentioned formulas (X) compound is new compound and can obtains by the compound that is expressed from the next and oxyamine or its reactant salt:

Wherein A, Y, m, n, R ¹, R ², R ³and R ⁴definition as above.

Many above-mentioned formulas (XI) compound is new compound and can obtains according to for example method described in WO 2004/067522.

Typical reaction method is represented by following scheme:

Wherein A, Y and m define as above.

The example that is used as the 4-cyanobenzaldehyde of above-mentioned reaction scheme raw material comprises 4-cyanobenzaldehyde, 4-cyano group-2-fluorobenzaldehyde, the chloro-4-cyanobenzaldehyde of 2-, the bromo-4-cyanobenzaldehyde of 2-, 4-cyano group-2-benzaldehyde iodine and 5-formyl radical pyridine-2-formonitrile HCN.Together with the carbon atom that two adjacent Y connect with them, form an optional substituted ring for example when phenyl ring, an example of the starting compound of above-mentioned reaction method scheme is 4-formyl radical naphthalene-1-formonitrile HCN.

Above-mentioned formula (XI) compound also can synthesize by the alternative approach being represented by following reaction scheme:

Wherein A, Y and m define as above.

The example that is used as the 4-tolyl aldehyde of above-mentioned reaction scheme raw material, comprises the fluoro-4-tolyl aldehyde of 3-, the chloro-4-tolyl aldehyde of 3-, the bromo-4-tolyl aldehyde of 3-, 4-methyl-3-benzaldehyde iodine, 3-methoxyl group-4-tolyl aldehyde, 4-methyl-3-nitro phenyl aldehyde and 6-methyl nicotine aldehyde.Together with the carbon atom that two adjacent Y connect with them, form an optional substituted ring for example when phenyl ring, an example of the starting compound of above-mentioned reaction method scheme is 4-methylnaphthalene-1-formaldehyde.

The example of preparing the halogenating agent in above-mentioned formula (II) compound comprises, for example chlorine, bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1,3-bis-chloro-5,5-T10,1,3-bis-is bromo-5,5-T10, benzyltrimethylammon.um tetrachloro iodide (benzyltrimethylammonium tetrachloroiodate), clorox etc.

The representative instance that is used as formula (II) compound of preparation method (a) Raw comprises 4-(acetylamino methyl)-N-hydroxybenzene carboxylic imino-chlorine, 4-(acetylamino methyl)-N-hydroxy-3-methyl benzene carboxylic imino-chlorine, the fluoro-N-hydroxybenzene of 4-(acetylamino methyl)-3-carboxylic imino-chlorine, the chloro-N-hydroxybenzene of 4-(acetylamino methyl)-3-carboxylic imino-chlorine, the bromo-N-hydroxybenzene of 4-(acetylamino methyl)-3-carboxylic imino-chlorine, 4-(acetylamino methyl)-N-hydroxyl-3-iodobenzene carboxylic imino-chlorine and 4-(acetylamino methyl)-N-hydroxyl-3-oil of mirbane carboxylic imino-chlorine.

Together with the carbon atom that two adjacent Y connect with them, form an optionally substituted ring for example when phenyl ring, an example of formula (II) compound is N-({ 4-[(oxyimino) methyl] naphthalene-1-yl } methyl) ethanamide.

Formula (III) compound as another raw material in preparation method (a) is contained for example with the known compound described in Publication about Document: Journal of Organic Chemistry, 1991, the 56 volumes, 7336-7340 page and 1994, the 59th volume, 2898-2901 page; Journal of FluorineChemistry, 1999, the 95 volumes, 167-170 page; With WO 2005/05085216.Described compound can synthesize by the method for describing in these publications.The representative instance of formula (III) compound comprises [1-(trifluoromethyl) vinyl] benzene, 1, the fluoro-5-[1-of 3-bis-(trifluoromethyl) vinyl] benzene, the chloro-3-[1-of 1-(trifluoromethyl) vinyl] benzene, 1, the chloro-5-[1-of 3-bis-(trifluoromethyl) vinyl] benzene, 1-trifluoromethyl-3-[1-(trifluoromethyl) vinyl] benzene, 1-trifluoromethyl-4-[1-(trifluoromethyl) vinyl] benzene, 1, two (trifluoromethyl)-5-[1-(trifluoromethyl) vinyl of 3-] benzene, 1, the bromo-5-[1-of 3-bis-(trifluoromethyl) vinyl] benzene, 1, 2, the chloro-5-[1-of 3-tri-(trifluoromethyl) vinyl] benzene and the fluoro-2-of 1-(trifluoromethyl)-4-[1-(trifluoromethyl) vinyl] benzene.

Preparation method (a) can be according to WO 2004/018410, WO 2005/085216, Tetrahedron (2000), the 56th volume, and method described in 1057-1064 page is implemented.

Preparation method's (a) reaction can be carried out in a kind of suitable thinner, the example of the described thinner that can use in the method for example comprises, aliphatic hydrocrbon (for example hexane, hexanaphthene, heptane), aromatic hydrocarbon (for example benzene, toluene, dimethylbenzene, chlorobenzene), alcohol (for example methyl alcohol, ethanol, Virahol), ether (for example diethyl ether, dibutyl ether, glycol dimethyl ether (DME), tetrahydrofuran (THF), dioxane), acid amides (for example dimethyl formamide (DMF), N,N-DIMETHYLACETAMIDE (DMA), N-Methyl pyrrolidone), nitrile (for example acetonitrile, propionitrile), methyl-sulphoxide (DMSO), water, or its mixture.

Preparation method's (a) reaction can be used a kind of following alkali to carry out: alkali metal base, comprises for example sodium carbonate, salt of wormwood, sodium bicarbonate, saleratus, sodium acetate, potassium acetate, sodium methylate, sodium ethylate and potassium tert.-butoxide; And organic bases, comprise triethylamine, diisopropylethylamine, Tributylamine, N-methylmorpholine, N, accelerine, N, N-Diethyl Aniline, the 4-tertiary butyl-DMA, pyridine, picoline, lutidine, diazabicyclo undecylene, diazabicyclo octane and imidazoles.

Preparation method's (a) reaction can be carried out in the temperature range of non-constant width.Usually, this reaction can be carried out at the temperature of approximately-78 DEG C to 200 DEG C, preferably-10 DEG C to approximately 150 DEG C.This reaction is preferably carried out under normal pressure, but it also can carry out under the pressure improving or reduce.Reaction times can be 0.1-72 hour, preferably 1-24 hour.

In enforcement preparation method (a), for example, 1 mole of formula (II) compound and 1-2 mole of formula (III) compound and 1 mole or slightly excessive a kind of alkali for example can be reacted in DMF at thinner, obtain the target compound of formula (I).

Formula (IV) compound as preparation method (b) Raw is new compound, and (e) to (k) obtains by the following method.

Preparation method (e) is (as R in formula (IV) ³represent that hydrogen and n are at 1 o'clock):

Described method is: make formula (XII) compound react to obtain formula (XIII) compound with halogenating agent, gained compound reacts with potassium phthalimide and obtains formula (XIV) compound, and is hydrolyzed gained compound,

Wherein A, R, X, l, Y, m, R ¹and R ²define as above,

Wherein A, R, X, l, Y, m, R ¹and R ²as above, and Hal represents halogen in definition,

Wherein A, R, X, l, Y, m, R ¹and R ²definition as above.

Preparation method (f)

Described method is: above-mentioned formula (XIII) compound is reacted with formula (XV) compound:

R ³-NH ₂ (XV)

Wherein R ³definition as above.

Preparation method (g) is (when n in formula (IV) represents 1 and R ¹and R ²while representing hydrogen):

Described method is: the reduction of formula (XVI) compound is obtained to formula (XVII) compound, gained compound reacts with methylsulfonyl chloride or halogenating agent and obtains formula (XVIII) compound, make subsequently gained compound react with above-mentioned formula (XV) compound

Wherein A, R, X, l, Y and m as above define, and R ⁵represent alkyl,

Wherein A, R, X, l, Y and m define as above,

Wherein A, R, X, l, Y, m and L define as above.

Preparation method (h) is (as R in formula (IV) ³while representing hydrogen):

Described method is: reduction-type (XIX) compound,

Wherein A, R, X, l, Y, m, n, R ¹and R ²definition as above.

In preparation method (e), some compounds of above-mentioned formula (XII) are the compound described in WO 2005/085216, and can obtain according to for example following preparation method (i) to (k).

Preparation method (i)

Described method is: above-mentioned formula (III) compound is reacted with formula (XX) compound,

Wherein A, Y, m, n, R ¹, R ²define as above with Hal.

Preparation method (j)

Described method is: make formula (XXI) compound molecule intramolecular cyclization,

Wherein A, R, X, l, Y, m, R ¹and R ²definition as above.

Preparation method (k)

Described method is: formula (XXII) compound is reacted with hydroxy amine hydrochloric acid salt,

Wherein A, R, X, l, Y, m, R ¹and R ²definition as above.

Some compounds of above-mentioned preparation method (i) Chinese style (XX) are new compound, and can obtain by the preparation method who is for example similar to above-mentioned preparation method (a) Chinese style (II) compound.

The representative instance of formula (XX) compound comprises:

N-hydroxy-4-methyl benzene carboxylic imino-chlorine, the fluoro-N-hydroxy-4-methyl of 3-benzene carboxylic imino-chlorine, the chloro-N-hydroxy-4-methyl of 3-benzene carboxylic imino-chlorine, the bromo-N-hydroxy-4-methyl of 3-benzene carboxylic imino-chlorine, the iodo-4-methylbenzene of N-hydroxyl-3-carboxylic imino-chlorine and N-hydroxy-4-methyl-3-oil of mirbane carboxylic imino-chlorine.Optionally substituted ring is for example when phenyl ring together with the carbon atom that two adjacent Y connect with them, to form one, and an example of formula (XX) compound is N-hydroxy-4-methyl naphthalene-1-carboxylic imino-chlorine.

Above-mentioned preparation method (j) can be according to for example J.Chem.Soc.Chem.Commun., the 16th volume, 1983, the 873-875 pages; Chem Pharm.Bull., the 12nd volume, method described in 1964, the 1189-1192 pages is implemented.

The chemical compound lot of above-mentioned formula (XXI) is new compound and can obtains by following formula (XXIII) compound and oxyamine or its reactant salt:

Wherein A, R, X, l, Y, m, R ¹and R ²definition as above.

The chemical compound lot of above-mentioned formula (XXIII) is new compound and can be according to for example ZhurnalOrganicheskoi Khimii, the 28th volume (No.3), and method described in 518-526 page is synthetic., the compound of formula (XXIII) can be by making formula (XXIV) compound react and obtain with formula (XXV) compound:

Wherein X, l and R define as above,

Wherein A, Y, m, n, R ¹and R ²definition as above.

The representative instance of above-mentioned formula (XXIV) compound comprises trifluoroacetophenone, 3 ', 5 '-bis-chloro-2, 2, 2-trifluoroacetophenone, 3 ', 4 '-bis-chloro-2, 2, 2-trifluoroacetophenone, 3 ', 4 ', 5 '-tri-chloro-2, 2, 2-trifluoroacetophenone, 3 '-fluoro-2, 2, 2-trifluoroacetophenone, 3 '-chloro-2, 2, 2-trifluoroacetophenone, 3 '-bromo-2, 2, 2-trifluoroacetophenone, 3 '-iodo-2, 2, 2-trifluoroacetophenone, 3 '-nitro-2, 2, 2-trifluoroacetophenone, 3 '-cyano group-2, 2, 2-trifluoroacetophenone, 3 '-(trifluoromethyl)-2, 2, 2-trifluoroacetophenone and 3 ', 5 '-bis-(trifluoromethyl)-2, 2, 2-trifluoroacetophenone.

The representative instance of above-mentioned formula (XXV) compound comprises 4-methyl acetophenone, the fluoro-4-methyl acetophenone of 2-, the chloro-4-methyl acetophenone of 2-, the bromo-4-methyl acetophenone of 2-, the iodo-4-methyl acetophenone of 2-, 4-methyl-2-nitro-acetophenone, 4-acetylbenzoic acid methyl esters, 4-ethanoyl-2-nitrobenzene methyl, 4-ethanoyl-2-iodo-benzoic acid methyl esters and 4-ethanoyl benzonitrile.Together with the carbon atom that two adjacent Y connect with them, form an optional substituted ring for example when phenyl ring, an example of formula (XXV) compound is 1-(4-methylnaphthalene-1-yl) ethyl ketone.

The representative instance of above-mentioned formula (XXIII) compound comprises:

3-(3, 5-dichlorophenyl)-4, 4, the fluoro-3-hydroxyl-1-of 4-tri-(4-aminomethyl phenyl) fourth-1-ketone, 3-(3, 5-dichlorophenyl)-4, 4, the fluoro-1-of 4-tri-(the fluoro-4-aminomethyl phenyl of 3-)-3-hydroxyl fourth-1-ketone, 1-(the chloro-4-aminomethyl phenyl of 3-)-3-(3, 5-dichlorophenyl)-4, 4, the fluoro-3-hydroxyl fourth-1-of 4-tri-ketone, 1-(the bromo-4-aminomethyl phenyl of 3-)-3-(3, 5-dichlorophenyl)-4, 4, the fluoro-3-hydroxyl fourth-1-of 4-tri-ketone, 3-(3, 5-dichlorophenyl)-4, 4, the fluoro-3-hydroxyl-1-of 4-tri-(the iodo-4-aminomethyl phenyl of 3-) fourth-1-ketone, 3-(3, 5-dichlorophenyl)-4, 4, the fluoro-3-hydroxyl-1-of 4-tri-(4-methyl-3-nitro phenyl) fourth-1-ketone and 4, 4, 4-tri-fluoro-3-hydroxyl-1-(4-aminomethyl phenyl)-3-[3-(trifluoromethyl) phenyl] fourth-1-ketone.Together with the carbon atom that two adjacent Y connect with them, form a ring optionally replacing for example when phenyl ring, an example of formula (XXIII) compound is 3-(3,5-dichlorophenyl)-4, the fluoro-3-hydroxyl-1-of 4,4-tri-(4-methylnaphthalene-1-yl) fourth-1-ketone.

Formula (XXII) compound in above-mentioned preparation method (k) is new compound, and can be reacted and obtain with thionyl chloride by above-mentioned formula (XXIII) compound.

The representative instance of formula (XXII) compound comprises: 4, 4, the fluoro-1-of 4-tri-(4-aminomethyl phenyl)-3-[3-(three fluoro-2-methyl-s) phenyl] but-2-ene-1-ketone, 3-(3, 5-dichlorophenyl)-4, 4, the fluoro-1-of 4-tri-(4-aminomethyl phenyl) but-2-ene-1-ketone, 3-(3, 5-dichlorophenyl)-4, 4, the fluoro-1-of 4-tri-(the fluoro-4-aminomethyl phenyl of 3-) but-2-ene-1-ketone, 1-(the chloro-4-aminomethyl phenyl of 3-)-3-(3, 5-dichlorophenyl)-4, 4, 4-trifluoro but-2-ene-1-ketone, 1-(the bromo-4-aminomethyl phenyl of 3-)-3-(3, 5-dichlorophenyl)-4, 4, 4-trifluoro but-2-ene-1-ketone, 3-(3, 5-dichlorophenyl)-4, 4, the fluoro-1-of 4-tri-(the iodo-4-aminomethyl phenyl of 3-) but-2-ene-1-ketone and 3-(3, 5-dichlorophenyl)-4, 4, the fluoro-1-of 4-tri-(4-methyl-3-nitro phenyl) but-2-ene-1-ketone.Together with the carbon atom that two adjacent Y connect with them, form an optional substituted ring for example when phenyl ring, an example of formula (XXII) compound is 3-(3,5-dichlorophenyl)-4, the fluoro-1-of 4,4-tri-(4-methylnaphthalene-1-yl) but-2-ene-1-ketone.

Above-mentioned formula (XV) compound in preparation method (f) is known compound, and comprises for example ammoniacal liquor, methylamine, ethamine, Tri N-Propyl Amine, Isopropylamine, cyclopropylamine, allylamine, propargylamine, benzylamine, 1-pyridine-2-base methylamine, 1-pyridin-3-yl methylamine, 1-pyridin-4-yl methylamine.

Above-mentioned formula (XVI) compound in preparation method (g) (l) or (m) obtain by the following method.

Preparation method (l)

Described method is: above-mentioned formula (III) compound is reacted with formula (XXVI) compound,

Wherein A, Y, m, Hal and R ⁵definition as above.

Preparation method (m)

Described method is: make (XXVII) compound molecule intramolecular cyclization,

Wherein A, R, X, l, Y, m and R ⁵definition as above.

Some compounds of above-mentioned preparation method (l) Chinese style (XXVI) are new compound and can use the preparation method who is for example similar to above-mentioned preparation method (a) Chinese style (II) compound to obtain.

The representative instance of formula (XXVI) compound comprises: 4-[chlorine (oxyimino) methyl] methyl benzoate, 4-[chlorine (oxyimino) methyl]-2-methyl-toluate, 4-[chlorine (oxyimino) methyl]-2-fluorophenyl carbamate, the chloro-4-[chlorine of 2-(oxyimino) methyl] methyl benzoate, the bromo-4-[chlorine of 2-(oxyimino) methyl] methyl benzoate, 4-[chlorine (oxyimino) methyl]-2-iodo-benzoic acid methyl esters and 4-[chlorine (oxyimino) methyl]-2-nitrobenzene methyl.Together with the carbon atom that two adjacent Y connect with them, form an optional substituted ring for example when phenyl ring, an example of formula (XXVI) compound be 4-[chlorine ((oxyimino) methyl] naphthalene-1-carboxylate methyl ester.

Above-mentioned preparation method (m) can implement according to the method that is similar to above-mentioned preparation method (j).The compound of above-mentioned formula (XXVII) can be by obtaining following formula: compound and oxyamine or its reactant salt:

Wherein A, R, X, l, Y, m and R ⁵definition as above.

The compound of above-mentioned formula (XXVIII) is new compound and can be by making above-mentioned formula (XXIV) compound react and obtain with following formula: compound:

Wherein A, Y, m and R ⁵definition as above.

The compound of above-mentioned formula (XXIX) is known compound; and for example comprise 4-acetylbenzoic acid methyl esters, 4-ethanoyl-2-methyl-toluate, 4-ethanoyl-2-fluorophenyl carbamate, 4-ethanoyl-2-chloro benzoic ether, 4-ethanoyl-2-methyl-bromobenzoate, 4-ethanoyl-2-iodo-benzoic acid methyl esters and 4-ethanoyl-2-nitrobenzene methyl.Together with the carbon atom that two adjacent Y connect with them, form an optional substituted ring for example when phenyl ring, an example of formula (XXIX) compound is 4-ethanoyl naphthalene-1-carboxylate methyl ester.

Above-mentioned preparation method (h) Chinese style (XIX) compound comprises known compound and can be according to for example J.Org.Chem., 1999, the 64 volumes, and described in 3171-3177 page, method is synthesized.

The representative instance of above-mentioned preparation method (e) Chinese style (XII) compound comprises, for example 5-(3, 5-dichlorophenyl)-3-(4-aminomethyl phenyl)-5-(trifluoromethyl)-4, 5-dihydro-isoxazole, 5-(3, 5-dichlorophenyl)-3-(the fluoro-4-aminomethyl phenyl of 3-)-5-(trifluoromethyl)-4, 5-dihydro-isoxazole, 3-(the chloro-4-aminomethyl phenyl of 3-)-5-(3, 5-dichlorophenyl)-5-(trifluoromethyl)-4, 5-dihydro-isoxazole, 3-(the bromo-4-aminomethyl phenyl of 3-)-5-(3, 5-dichlorophenyl)-5-(trifluoromethyl)-4, 5-dihydro-isoxazole, 5-(3, 5-dichlorophenyl)-3-(the iodo-4-aminomethyl phenyl of 3-)-5-(trifluoromethyl)-4, 5-dihydro-isoxazole and 5-(3, 5-dichlorophenyl)-3-(4-methyl-3-nitro phenyl)-5-(trifluoromethyl)-4, 5-dihydro-isoxazole.Together with the carbon atom that two adjacent Y connect with them, form an optional substituted ring for example when phenyl ring, an example of formula (XII) compound is 5-(3,5-dichlorophenyl)-3-(4-methylnaphthalene-1-yl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole.

The representative instance of preparation method (g) Chinese style (XVI) compound comprises:

4-[5-(3, 5-dichlorophenyl)-5-(trifluoromethyl)-4, 5-dihydro-isoxazole-3-yl] methyl benzoate, 4-[5-(3, 5-dichlorophenyl)-5-(trifluoromethyl)-4, 5-dihydro-isoxazole-3-yl]-2-methyl-toluate, 4-[5-(3, 5-dichlorophenyl)-5-(trifluoromethyl)-4, 5-dihydro-isoxazole-3-yl] 2-fluorophenyl carbamate, the chloro-4-[5-(3 of 2-, 5-dichlorophenyl)-5-(trifluoromethyl)-4, 5-dihydro-isoxazole-3-yl] methyl benzoate, the bromo-4-[5-(3 of 2-, 5-dichlorophenyl)-5-(trifluoromethyl)-4, 5-dihydro-isoxazole-3-yl] methyl benzoate, 4-[5-(3, 5-dichlorophenyl)-5-(trifluoromethyl)-4, 5-dihydro-isoxazole-3-yl]-2-iodo-benzoic acid methyl esters, and 4-[5-(3, 5-dichlorophenyl)-5-(trifluoromethyl)-4, 5-dihydro-isoxazole-3-yl]-2-nitrobenzene methyl.Together with the carbon atom that two adjacent Y connect with them, form an optionally substituted ring for example when phenyl ring, an example of formula (XVI) compound is 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] naphthalene-1-carboxylicesters.

The representative instance of preparation method (h) Chinese style (XIX) compound comprises:

4-[5-(3, 5-dichlorophenyl)-5-(trifluoromethyl)-4, 5-dihydro-isoxazole-3-yl] benzonitrile, 4-[5-(3, 5-dichlorophenyl)-5-(trifluoromethyl)-4, 5-dihydro-isoxazole-3-yl]-2-methyl benzonitrile, 4-[5-(3, 5-dichlorophenyl)-5-(trifluoromethyl)-4, 5-dihydro-isoxazole-3-yl]-2-fluorine benzonitrile, the chloro-4-[5-(3 of 2-, 5-dichlorophenyl)-5-(trifluoromethyl)-4, 5-dihydro-isoxazole-3-yl] benzonitrile, the bromo-4-[5-(3 of 2-, 5-dichlorophenyl)-5-(trifluoromethyl)-4, 5-dihydro-isoxazole-3-yl] benzonitrile, 4-[5-(3, 5-dichlorophenyl)-5-(trifluoromethyl)-4, 5-dihydro-isoxazole-3-yl]-2-iodine benzonitrile, 4-[5-(3, 5-dichlorophenyl)-5-(trifluoromethyl)-4, 5-dihydro-isoxazole-3-yl]-2-nitrobenzonitrile, { 4-[5-(3, 5-dichlorophenyl)-5-(trifluoromethyl)-4, 5-dihydro-isoxazole-3-yl] phenyl } acetonitrile and { the bromo-4-[5-(3 of 2-, 5-dichlorophenyl)-5-(trifluoromethyl)-4, 5-dihydro-isoxazole-3-yl] phenyl } acetonitrile.Together with the carbon atom that two adjacent Y connect with them, form an optional substituted ring for example when phenyl ring, an example of formula (XIX) compound is 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] naphthalene-1-formonitrile HCN.

Formula (V) compound as preparation method (b) Raw is the known compound in organic chemistry filed and comprises for example Acetyl Chloride 98Min., propionyl chloride, pivalyl chloride, acryloyl chloride, methyl-chloroformate, N, N-dimethyl carbamyl chloride, cyclopropyl carbonyl chloride, N, N-dimethyl sulphide is for carbamyl chloride, Benzoyl chloride, nicotinoyl chlorine, diacetyl oxide, trifluoroacetic anhydride, methylsulfonyl chloride.

Preparation method's (b) reaction can be carried out in a kind of suitable thinner, described thinner for example comprises, aliphatic hydrocrbon (for example hexane, hexanaphthene, heptane), aromatic hydrocarbon (for example benzene, toluene, dimethylbenzene, chlorobenzene), ether (for example diethyl ether, dibutyl ether, glycol dimethyl ether (DME), tetrahydrofuran (THF), dioxane), acid amides (for example dimethyl formamide (DMF), N,N-DIMETHYLACETAMIDE (DMA), N-Methyl pyrrolidone), nitrile (for example acetonitrile, propionitrile), methyl-sulphoxide (DMSO), water, or its mixture.

Preparation method's (b) reaction can be used a kind of following alkali to carry out: alkali metal base, comprises lithium hydride, sodium hydride, potassium hydride KH, lithium amide, sodium amide, diisopropylaminoethyl lithium, butyllithium, tert-butyl lithium, trimethyl silyl lithium, the silica-based Lithamide of hexamethyl two (lithiumhexamethyldisilazide), sodium carbonate, salt of wormwood, sodium acetate, potassium acetate, sodium methylate, sodium ethylate, potassium tert.-butoxide; And organic bases, comprise triethylamine, diisopropylethylamine, Tributylamine, N-methylmorpholine, N, accelerine, N, N-Diethyl Aniline, the 4-tertiary butyl-DMA, pyridine, picoline, lutidine, diazabicyclo undecylene, diazabicyclo octane, imidazoles.

Preparation method's (b) reaction can be carried out in wide temperature range.Conventionally, this reaction can approximately-78 DEG C to approximately 200 DEG C, preferably at the temperature of approximately-10 DEG C to approximately 150 DEG C, carry out.This reaction is preferably carried out under approximately 1000 mbar at normal pressure, but its can the pressure improving under pressure more than 1000 mbar or the pressure reducing under the pressure below 1000 mbar, carry out.Reaction times can be in the scope of 0.1-72 hour, preferably 0.1-24 hour.

In enforcement preparation method (b), for example 1 mole of formula (IV) compound can be with 1 to 3 mole of formula (V) compound, under the existence of a kind of alkali of 1 mole to 3 moles, for example, in thinner (DMF), react, and obtains the target compound of formula (I).

Formula (VI) compound as preparation method (c) Raw is new compound and can obtains by for example following methods (n) to (p).

Preparation method (n)

Described method is: following formula: compound is reacted with above-mentioned formula (III) compound,

Wherein A, Y, m, n, R ¹, R ², R ⁴define as above with Hal.

Preparation method (o)

Described method is: following formula: compound is reacted with above-mentioned formula (VII) compound,

Wherein A, R, X, l, Y, m, n, R ¹and R ²definition as above.

Preparation method (p)

Described method is: above-mentioned formula (VIII) compound is reacted with following formula: compound,

R ⁴-NH ₂ (XXXII)

Wherein R ⁴definition as above.

Above-mentioned preparation method (n) Chinese style (XXX) compound is that new compound and preparation method's that can be by being similar to above-mentioned preparation method (a) Chinese style (II) compound method obtains.

The representative instance of formula (XXX) compound for example comprises:

4-(formamido-methyl)-N-hydroxybenzene carboxylic imino-chlorine, 4-(acetylamino methyl)-N-hydroxybenzene carboxylic imino-chlorine, 4-(acetylamino methyl)-N-hydroxy-3-methyl benzene carboxylic imino-chlorine, the fluoro-N-hydroxybenzene of 4-(acetylamino methyl)-3-carboxylic imino-chlorine, the chloro-N-hydroxybenzene of 4-(acetylamino methyl)-3-carboxylic imino-chlorine, the bromo-N-hydroxybenzene of 4-(acetylamino methyl)-3-carboxylic imino-chlorine, 4-(acetylamino methyl)-N-hydroxyl-3-iodobenzene carboxylic imino-chlorine and 4-(acetylamino methyl)-N-hydroxyl-3-oil of mirbane carboxylic imino-chlorine.Optionally substituted ring is for example when phenyl ring together with the carbon atom that two adjacent Y connect with them, to form one, and an example of formula (XXX) compound is 4-[(kharophen) methyl]-N-hydroxyl naphthalene-1-carboxylic imino-chlorine.

Formula (XXXI) compound in above-mentioned preparation method (o) and wherein R ³for above-mentioned formula (IV) Compound Phase of hydrogen is worked as.

Formula (XXXII) compound in preparation method (p) is known compound, and for example comprises, methane amide, ethanamide, propionic acid amide, 2,2,2-trifluoroacetamide, benzamide, urethanum and second sulphamide.

Preparation method's (c) reaction can be carried out under the condition identical with above-mentioned preparation method (b).

Some formulas (VIII) compound as preparation method (d) Raw is worked as with above-mentioned formula (XIII) and some Compound Phases (XVIII).

The amide compound of above-mentioned formula (IX) is known compound, and for example comprises, ethanamide, 2,2,2-trifluoroacetamide, 2,2, the fluoro-N-methylacetamide of 2-tri-and pyrrolidin-2-one, piperidines-2-ketone, N-(pyridine-2-ylmethyl) ethanamide.

Preparation method's (d) reaction can be carried out under the condition identical with above-mentioned preparation method (b).

The compounds of this invention has and effectively kills insect and kill acarid activity.Therefore the compound, being represented by formula of the present invention (I) or formula (Ia) can be used as insecticide and miticide.They are used in particular in agriculture field.The compounds of this invention also has suitable preventive and therapeutic effect to harmful insect and to cultivated plant plant-less toxicity.In addition, the compounds of this invention can be used for preventing and treating various pests, for example comprise the insect of the parasitic insect of harmful piercing-sucking mouthparts insect, chewing mouthparts insect and other plant, pest of stored grain and sanitary insect pest and veterinary applications, and can be used for control to it, particularly eradicate and go out and remove.Therefore, a kind of method of resisting harmful insect is also contained in the present invention.

The compounds of this invention is because having the toxicity of good plant tolerance and favourable warm-blooded animal concurrently and having good environmental resistance; be suitable for protective plant and plant organ, raising gather productive rate, the quality of improving harvested material and control animal nuisance (animal pest), the insect, arachnid, worm, nematode and the mollusk that particularly in protection, health field and the animal health field of agricultural, gardening, livestock industry, forest, gardens and leisure facilities, storage product and material, run into.They can be preferably used as plant protection product.They have activity to common sensitivity and resistance species and to all or some etap.Can the application of the invention compound and the composition insect of resisting especially comprise:

Anoplura (Anoplura) (Phthiraptera), for example, Damalinia (Damalinia spp.), Haematopinus (Haematopinus spp.), Linognathus (Linognathus spp.), lice belong to (Pediculus spp.), Trichodectes (Trichodectes spp.).

Arachnida (Arachnida), for example, Acarus siro (Acarus siro), oranges and tangerines aceria (Aceria sheldoni), peronium Eriophyes (Aculops spp.), acupuncture Eriophyes (Aculusspp.), Amblyomma (Amblyomma spp.), Argas (Argas spp.), Boophilus (Boophilus spp.), short whisker Acarapis (Brevipalpus spp.), Bryobia praetiosa (Bryobiapraetiosa), Chorioptes (Chorioptes spp.), Dermanyssus gallinae (Dermanyssus gallinae), Eotetranychus (Eotetranychus spp.), goitre mite on pears (Epitrimerus pyri), true Tetranychus (Eutetranychus spp.), Eriophyes (Eriophyes spp.), half Tarsonemus (Hemitarsonemus spp.), Hyalomma (Hyalomma spp.), hard tick belongs to (Ixodesspp.), latrodectus mactans (Latrodectus mactans), Metatetranychus spp., Oligonychus (Oligonychus spp.), Ornithodoros (Ornithodoros spp.), Panonychus citri belongs to (Panonychus spp.), the tangerine rust mite (Phyllocoptruta oleivora) that rues, Polyphagotarsonemus latus Banks (Polyphagotarsonemus latus), Psoroptes (Psoroptes spp.), Rh (Rhipicephalus spp.), root mite belongs to (Rhizoglyphus spp.), itch mite belongs to (Sarcoptes spp.), Middle East gold scorpion (Scorpio maurus), Stenotarsonemus spp., Tarsonemus (Tarsonemus spp.), Tetranychus (Tetranychus spp.), Vasateslycopersici.

Bivalva guiding principle, for example, Dreissena spp..

Lip foot order (Chilopoda), for example, DIWUGONG belongs to (Geophilus spp.), Scutigeraspp..

Coleoptera (Coleoptera), for example, acanthoscelides obtectus (Acanthoscelides obtectus), beak rutelian belongs to (Adoretus spp.), willow firefly chrysomelid (Agelastica alni), click beetle belongs to (Agriotes spp.), the potato melolonthid (Amphimallon solstitialis), furniture death watch beetle (Anobium punctatum), Genus Anoplophora Hope (Anoplophora spp.), flower resembles genus (Anthonomus spp.), Anthrenus (Anthrenus spp.), Ah gill cockchafer belongs to (Apogonia spp.), Atomaria spp., moth-eaten belong to (the Attagenus spp.) of fur, dislike bar bean weevil (Bruchidius obtectus), bean weevil belongs to (Bruchus spp.), tortoise resembles genus (Ceuthorhynchus spp.), Cleonus mendicus, wide chest Agriotes spp (Conoderus spp.), collar resembles genus (Cosmopolites spp.), the brown New Zealand rib wing melolonthid (Costelytra zealandica), Curculio (Curculio spp.), the hidden beak of Yang Gan resembles (Cryptorhynchus lapathi), khapra beetle belongs to (Dermestes spp.), chrysomelid genus (Diabrotica spp.), epilachna genus (Epilachna spp.), Faustinus cubae, globose spider beetle (Gibbium psylloides), black different pawl sugarcane cockchafer (Heteronychus arator), Hylamorpha elegans, North America house longhorn beetle (Hylotrupes bajulus), alfalfa leaf resembles (Hypera postica), Hypothenemus spp., the large brown hock gill cockchafer of sugarcane (Lachnosterna consanguinea), colorado potato bug (Leptinotarsadecemlineata), rice root weevil (Lissorhoptrus oryzophilus), cylinder beak resembles genus (Lixusspp.), moth-eaten belong to (the Lyctus spp.) of powder, pollen beetle (Meligethes aeneus), the west melolonthid in May (Melolontha melolontha), Migdolus spp., China ink day Bos (Monochamus spp.), Naupactus xanthographus, golden spider beetle (Niptushololeucus), coconut palm moth rhinoceros cockchafer (Oryctes rhinoceros), saw-toothed grain beetle (Oryzaephilussurinamensis), black grape ear image (Otiorrhynchus sulcatus), little blue and white cockchafer (Oxycetonia jucunda), horseradish ape chrysomelid (Phaedon cochleariae), food phyllobranchia cockchafer belongs to (Phyllophaga spp.), Japan popillia flavosellata fairmaire (Popillia japonica), Premnotrypes spp., rape golden head flea beetle (Psylliodes chrysocephala), Ptinus (Ptinus spp.), dark-coloured ladybug (Rhizobius ventralis), lesser grain borer (Rhizoperthadominica), grain weevil belongs to (Sitophilus spp.), point Rhynchophorus (Sphenophorusspp.), stem resembles genus (Sternechus spp.), Symphyletes spp., tenebrio molitor (Tenebriomolitor), Tribolium (Tribolium spp.), spot khapra beetle belongs to (Trogoderma spp.), seed resembles genus (Tychius spp.), ridge tiger day Bos (Xylotrechus spp.), belong to (Zabrus spp.) apart from ground beetle, and Callosobruchus chinensis (Callosobruchus Chinensis), sitophilus zea-mais (Sitophilus zeamais), red flour beetle (Tribolium Castaneum), potato bug (Epilachna vigintioctomaculata), Agriotes subrittatus Motschulsky (Agriotesfuscicollis), Anomala rufocuprea, Leptinotarsa decemlineata, corn rootworm (Diabrotica spp.), Monochamus alternatus (Monochamus alternatus), rice water resembles (Lissorhoptrus oryzophilus), Lyctus bruneus and aulacophora femoralis (Aulacophora femoralis).

Collembola (Collembola), for example, arms Onychiurus arcticus (Onychiurus armatus).

Dermaptera (Dermaptera), for example, European earwig (Forficula auricularia).

Doubly sufficient order (Diplopoda), for example, Blaniulus guttulatus.

Diptera (Diptera), for example, Aedes (Aedes spp.), Anopheles (Anophelesspp.), garden march fly (Bibio hortulanus), calliphora erythrocephala (Calliphoraerythrocephala), Mediterranean Sea Ceratitis spp (Ceratitis capitata), Carysomyia (Chrysomyiaspp.), Callitroga (Cochliomyia spp.), Cordylobia anthropophaga, Culex (Culex spp.), Cuterebra (Cuterebra spp.), the large trypetid of olive (Dacus oleae), human botfly (Dermatobia hominis), Drosophila (Drosophila spp.), Fannia (Fanniaspp.), Gasterophilus (Gastrophilus spp.), Hylemyia (Hylemyia spp.), Hyppoboscaspp., Hypoderma (Hypoderma spp.), Liriomyza (Liriomyza spp.), Lucilia (Lucilia spp.), Musca (Musca spp.), Bemisia spp (Nezara spp.), Oestrus (Oestrus spp.), Oscinella frit (Oscinella frit), lamb's-quarters spring fly (Pegomyiahyoscyami), Phorbia (Phorbia spp.), Genus Stomoxys (Stomoxys spp.), Gadfly (Tabanus spp.), Tannia spp., Europe daddy-longlegs (Tipula paludosa), Wohlfahrtia (Wohlfahrtia spp.), and housefly (Musca domestica), Aedes aegypti (Aedesaegypti), kind fly (Hylemia platura), northern house (Culex pipiens), Anopheles sinensis (Anopheles sinensis), Culex tritaeniorhynchus (Culex tritaeniorhychus) and Liriomyza trifolii (Liriomyza trifolii).

Gastropoda (Gastropoda), for example, Arion spp., Biomphalaria (Biomphalariaspp.), little Bulinus (Bulinus spp.), Deroceras spp., native snail belong to (Galba spp.), Lymnaea (Lymnaea spp.), Katayama (Oncomelania spp.), amber spiro spp (Succinea spp.).

Worm guiding principle (Helminth), for example, Ancylostoma duodenale (Ancylostomaduodenale), Sri Lanka hook worm (Ancylostoma ceylanicum), ancylostoma braziliense (Acylostoma braziliensis), Ancylostoma (Ancylostoma spp.), seemingly draw ascarid nematode (Ascaris lubricoides), Ascaris (Ascaris spp.), cloth Shandong, Malaysia nematode (Brugia malayi), cloth Shandong, Timor nematode (Brugia timori), Bunostomum (Bunostomum spp.), Chabertia belongs to (Chabertia spp.), branch testis fluke belongs to (Clonorchis spp.), Cooperia (Cooperia spp.), Dicrocoelium (Dicrocoelium spp.), dictyocaulus filaria (Dictyocaulus filaria), fish tapeworm (Diphyllobothrium latum), guinea worm (Dracunculusmedinensis), Echinococcus granulosus (Echinocoecus granulosus), Echinococcus multilocularis (Echinococcus multilocularis), pinworm (Enterobiusvermicularis), Faciola spp., blood Trichinella (Haemonchus spp.), Heterakis (Heterakis spp.), short and smallly nibble shell tapeworm (Hymenolepis nana), Metastrongylus apri belongs to (Hyostrongulus spp.), loa loa (Loa Loa), Nematodirus (Nematodirus spp.), oesophagostomum (Oesophagostomum spp.), Opisthorchis (Opisthorchis spp.), Onchocerca caecutiens (Onchocerca volvulus), this off-line Eimeria difficult to understand (Ostertagia spp.), Paragonimus (Paragonimus spp.), Schistosomen spp., Fu Shi quasi-colubriformis (Strongyloides fuelleborni), strongyloides intestinalis (Strongyloides stercoralis), excrement Strongylus (Stronyloides spp.), taeniasis bovis (Taenia saginata), taeniasis suis (Taenia solium), trichina(Trichinella spiralis) (Trichinella spiralis), Trichinella nativa (Trichinella nativa), strain Bu Shi Trichinella spiralis (Trichinella britovi), south Trichinella spiralis (Trichinella nelsoni), Trichinellapseudopsiralis, trichostrongylus (Trichostrongulus spp.), Trichuris trichuria, wuchereria bancrofti (Wuchereria bancrofti).

In addition, also can prevent and treat protozoon, for example eimeria (Eimeria).

Heteroptera (Heteroptera), for example, squash bug (Anasa tristis), intend beautiful stinkbug and belong to (Antestiopsis spp.), soil chinch bug belongs to (Blissus spp.), pretty fleahopper belongs to (Calocorisspp.), Campylomma livida, different back of the body chinch bug belongs to (Cavelerius spp.), Cimex (Cimex spp.), Creontiades dilutus, pepper coried (Dasynus piperis), Dichelops furcatus, the long excellent lace bug of Hou Shi (Diconocoris hewetti), red cotton bug belongs to (Dysdercus spp.), America stinkbug belongs to (Euschistus spp.), Eurygasterspp belongs to (Eurygasterspp.), Heliopeltis spp., Horcias nobilellus, Leptocorisa spp belongs to (Leptocorisa spp.), leaf beak coried (Leptoglossus phyllopus), lygus bug belongs to (Lygus spp.), the black chinch bug of sugarcane (Macropes excavatus), Miridae (Miridae), Bemisia spp, Oebalus spp., Pentomidae, side butt stinkbug (Piesma quadrata), wall stinkbug belongs to (Piezodorus spp.), cotton pseudo-spot leg fleahopper (Psallus seriatus), Pseudacysta persea, Rhodnius (Rhodnius spp.), Sahlbergella singularis (Sahlbergella singularis), black stinkbug belongs to (Scotinophora spp.), pear crown network pentatomidae (Stephanitis nashi), Tibraca spp., Triatoma (Triatoma spp.).

Homoptera (Homoptera), for example, without net long tube Aphis (Acyrthosipon spp.), Aeneolamia spp., Aphalaridae (Agonoscena spp.), Aleurodes spp., sugarcane Aleyrodes (Aleurolobus barodensis), Aleurothrixus spp., Mango fruit leafhopper belongs to (Amrasca spp.), Anuraphis cardui, kidney Aspidiotus belongs to (Aonidiella spp.), Soviet Union bloom aphid (Aphanostigma piri), Aphis (Aphis spp), grape leafhopper (Arboridiaapicalis), roundlet armored scale belongs to (Aspidiella spp.), Aspidiotus belongs to (Aspidiotus spp.), Atanus spp., eggplant ditch is without net aphid (Aulacorthum solani), Bemisia spp., Lee's short-tail aphid (Brachycaudus helichrysii), Brachycolus spp., brevicoryne brassicae (Brevicorynebrassicae), little brown back rice plant hopper (Calligypona marginata), Carneocephala fulgida, cane powder angle aphid (Ceratovacuna lanigera), Cercopidae (Cercopidae), lecanium belongs to (Ceroplastes spp.), strawberry nail aphid (Chaetosiphon fragaefolii), sugarcane Huang Xue armored scale (Chionaspis tegalensis), tea green leafhopper (Chlorita onukii), walnut blackspot aphid (Chromaphis juglandicola), dark brown Aspidiotus (Chrysomphalus ficus), corn leafhopper (Cicadulina mbila), Coccomytilus halli, soft a red-spotted lizard belongs to (Coccus spp.), the hidden knurl aphid of tea Fischer (Cryptomyzus ribis), Dalbulus spp., Dialeurodes spp., Diaphorina spp., white back of the body armored scale belongs to (Diaspis spp.), Doralis spp., carry out giant coccid and belong to (Drosicha spp.), western rounded tail Aphis (Dysaphis spp.), ash mealybug belongs to (Dysmicoccusspp.), Empoasca flavescens (Empoasca spp.), woolly aphid belongs to (Eriosoma spp.), Erythroneura spp., Euscelis bilobatus, coffee ground mealybug (Geococcus coffeae), phony disease of peach poison leafhopper (Homalodisca coagulata), mealy plum aphid (Hyalopterusarundinis), icerya purchasi belongs to (Icerya spp.), sheet angle leafhopper belongs to (Idiocerus spp.), flat beak leafhopper belongs to (Idioscopus spp.), small brown rice planthopper (Laodelphax striatellus), Lecaniumspp., lepidosaphes shimer (Lepidosaphes spp.), radish aphid (Lipaphis erysimi), long tube Aphis (Macrosiphum spp.), Mahanarva fimbriolata, kaoliang aphid (Melanaphis sacchari), Metcalfiella spp., wheat is without net aphid (Metopolophiumdirhodum), the flat wing spot of black edge aphid (Monellia costalis), Monelliopsis pecanis, tumor aphid genus (Myzus spp.), lettuce is patched up Macrosiphus spp (Nasonovia ribisnigri), rice green leafhopper belongs to (Nephotettix spp.), brown paddy plant hopper (Nilaparvata lugens), Oncometopiaspp., Orthezia praelonga, red bayberry edge aleyrodid (Parabemisia myricae), Paratriozaspp., Parlatoria (Parlatoria spp.), Pemphigus (Pemphigus spp.), corn plant hopper (Peregrinus maidis), Phenacoccus (Phenacoccus spp.), Yang Ping wing woolly aphid (Phloeomyzus passerinii), phorodon aphid (Phorodon humuli), Phylloxeraspp., the brown point of sago cycas armored scale (Pinnaspis aspidistrae), stern line mealybug belongs to (Planococcusspp.), the former giant coccid of pyriform (Protopulvinaria pyriformis), white mulberry scale (Pseudaulacaspis pentagona), mealybug belongs to (Pseudococcus spp.), Psylla spp (Psylla spp.), tiny golden wasp belongs to (Pteromalus spp.), Pyrilla spp., large bamboo hat with a conical crown and broad brim Aspidiotus belongs to (Quadraspidiotus spp.), Quesada gigas, flat thorn mealybug belongs to (Rastrococcusspp.), Rhopalosiphum (Rhopalosiphum spp.), black bourch belongs to (Saissetia spp.), Scaphoides titanus, green bugs (Schizaphis graminum), sago cycas thorn Aspidiotus (Selenaspidus articulatus), long clypeus plant hopper belongs to (Sogata spp.), white backed planthopper (Sogatella furcifera), Sogatodes spp., Stictocephala festina, Tenalapharamalayensis, Tinocallis caryaefoliae, wide chest froghopper belongs to (Tomaspis spp.), sound Aphis (Toxoptera spp.), greenhouse whitefly (Trialeurodes vaporariorum), individual Psylla spp (Trioza spp.), jassids belongs to (Typhlocyba spp.), point armored scale belongs to (Unaspisspp.), Viteus vitifolii.

Hymenoptera (Hymenoptera), for example, Diprion (Diprion spp.), real tenthredinidae (Hoplocampa spp.), hair ant belong to (Lasius spp.), MonomoriumMayr (Monomoriumpharaonis), Vespa (Vespa spp.).

Isopoda (Isopoda), for example, pillworm (Armadillidium vulgare), comb beach louse (Oniscus asellus), ball pillworm (Porcellio scaber).

Isoptera (Isoptera), for example, Reticulitermes (Reticulitermes spp.), odontotermes (Odontotermes spp.); And eastern subterranean termite (Reticulitermes speratus) and Coptotermes formosanus Shtrari． (Coptotermes formosanus).

Lepidopteran (Lepidoptera), for example, Sang Jian Autographa spp (Acronicta major), tired noctuid (Aedia leucomelas), Agrotis (Agrotis spp.), cotton leaf ripple noctuid (Alabama argillacea), dry very Noctua (Anticarsia spp.), Barathrabrassicae, cotton lyonetid (Bucculatrix thurberiella), loose looper (Bupalus piniarius), flax yellow volume moth (Cacoecia podana), Capua reticulana, codling moth (Carpocapsa pomonella), winter geometrid moth (Cheimatobia brumata), straw borer spp (Chilo spp.), spruce bunworm (Choristoneura fumiferana), grape codling moth (Clysia ambiguella) (Clysia ambiguella), Cnaphalocerus spp., earias insulana (Eariasinsulana), Anagasta kuehniella (Ephestia kuehniella), pornography and drug moth (Euproctischrysorrhoea), cutworm belongs to (Euxoa spp.), the dirty Noctua (Feltia spp.) of cutting, greater wax moth (Galleria mellonella), Helicoverpa spp., Heliothis (Heliothisspp.), brownly knit moth (Hofmannophila pseudospretella), tea long paper moth (Homonamagnanima), apple ermine moth (Hyponomeuta padella), greedy Noctua (Laphygmaspp.), the thin moth of apple (Lithocolletis blancardella), green fruit winter noctuid (Lithophaneantennata), the white grand cutworm of beans (Loxagrotis albicosta), Euproctis (Lymantriaspp.), malacosoma neustria (Malacosoma neustria), lopper worm (Mamestrabrassicae), rice hair shin noctuid (Mocis repanda), mythimna separata (Mythimma separata), Oria spp., Oulema oryzae (Oulema oryzae), small noctuid (Panolis flammea), Pectinophora gossypiella (Pectinophora gossypiella), tangerine lyonetid (Phyllocnistis citrella), Pieris spp (Pieris spp.), diamond-back moth (Plutella xylostella), spodoptera (Prodeniaspp.), Pseudaletia spp., soybean noctuid (Pseudoplusia includens), Pyrausta nubilalis (Hubern). (Pyrausta nubilalis), Spodoptera (Spodoptera spp.), Thermesiagemmatalis, bag rain moth (Tinea pellionella), curtain rain moth (Tineola bisselliella), the green volume moth of oak (Tortrix viridana), powder Noctua (Trichoplusia spp.), and gypsymoth (Lymantria dispar), malacosoma neustria (Malacosoma neustria), cabbage caterpillar (Pieris rapae), prodenia litura (Spodoptera litura), lopper worm (Mamestrabrassicae), striped rice borer (Chilo suppressalis), Pyrausta nubilalis (Hubern). (Pyrausta nubilalis), Ephestia cautella, apple volume moth (Adoxophyes orana), codling moth (Carpocapsapomonella), the blue or green cutworm of swallow (Agrotis fucosa), greater wax moth (Galleria mellonella), small cabbage moth (Plutella maculipennis), Heliothis virescens (Heliothis virescens) and tangerine lyonetid (Phyllocnistis citrella).

Orthoptera (Orthoptera), for example, the Xi of family (Acheta domesticus), oriental cockroach (Blatta orientalis), Gryllotalpa spp (Gryllotalpa spp.), leucophaea maderae (Leucophaea maderae), migratory locusts belong to (Locusta spp.), black locust belongs to (Melanoplusspp.), desert locust (Schistocerca gregaria); And blatta germanica (Blattella germanica), periplaneta americana (Periplaneta americana), African mole cricket (Gryllotalpa africana) and African migratory locust (Locusta migratoria migratoriaodes).

Siphonaptera (Siphonaptera), for example, Ceratophyllus (Ceratophyllus spp.), Xanthopsyllacheopis (Xenopsylla cheopis).

Comprehensive order (Symphyla), for example, Scutigerella immaculata.

Thysanoptera (Thysanoptera), for example, rice thrips (Baliothrips biformis), Enneothrips flavens, flower thrips belong to (Frankliniella spp.), net Thrips (Heliothripsspp.), greenhouse bar hedge thrips (Hercinothrips femoralis), card Thrips (Kakothripsspp.), grape thrips (Rhipiphorothrips cruentatus), hard Thrips (Scirtothripsspp.), Taeniothrips cardamoni, Thrips (Thrips spp.); And palm thrips (Thrips palmi) and Frankliniella occidentalis (Frankliniella occidentalis).

Hemiptera, for example rice green leafhopper (Nephotettix cincticeps), brown paddy plant hopper (Nilaparvatalugens), Kang Shi mealybug (Pseudococcus comstocki), unaspis shield kuwana (Unaspisyanonensis), black peach aphid (Myzus persicas), apple aphid (Aphis pomi), cotten aphid (Aphis gossypii), turnip aphid (Rhopalosiphum pseudobrassicas), pear crown network pentatomidae (Stephanitis nashi), Nazara spp., Trialeurodes vaporariorum Westwood (Trialeurodesvaporariorm) and Pshylla spp.,

Thysanura (Thysanura), for example, silverfish (Lepisma saccharina).

Plant nematode comprises, for example, and eel Turbatrix (Anguina spp.), Aphelenchoides (Aphelenchoides spp.), thorn Turbatrix (Belonoaimus spp.), Bursaphelenchus (Bursaphelenchus spp.), fuller's teasel Ditylenchus dipsaci (Ditylenchus dipsaci), ball Heterodera (Globodera spp.), spiral-line Eimeria (Heliocotylenchus spp.), Heterodera (Heterodera spp.), minute hand Turbatrix (Longidorus spp.), Meloidogyne (Meloidogyne spp.), similar similes thorne (Radopholus similis), shallow bid spin line Eimeria (Rotylenchus spp.), burr Turbatrix (Trichodorus spp.), Tylenchorhynchus (Tylenchorhynchus spp.), pulvinulus sword Turbatrix (Tylenchulus spp.), the nematode (Tylenchulus semipenetrans) of partly puncturing, Xiphinema (Xiphinema spp.), and Meloidogyne incognita (Meloidogyne incognita), Bursaphelenchus lignicolusMamiya et Kiyohara, aphelenchoides besseyi (Aphelenchoides besseyi) and soybean cyst nematode Heterodera glycines (Heterodera glycines) and Pratylenchidae genus (Pratylenchus spp.).

Acarid for example comprises, carmine spider mite (Tetranychus cinnabarinus), Tetranychus urticae (Tetranychus urticae), citrus red mite (crm) (Panonychus citri), Aculopspelekassi and instep line genus (Tarsonemus spp.).

If suitable, the compounds of this invention also can finite concentration or rate of application as weedicide, safener, growth regulator or improve the medicament of plant characteristic, or as microbicide, for example mycocide, antimycotic agent, bactericide, virucide (comprising the medicament of resisting viroid) or the medicament as opposing MLO (mycoplasma-like organism(MLO)) and RLO (rickettsia-like organism).If suitable, they also can be used as intermediate or the precursor of synthetic other active compounds.

In veterinary applications, new compound of the present invention can be effectively for example, for resisting multiple pest parasite (vermin and endoparasite), insect and worm.

The example of described zooparasite comprises following insect:

Insect, comprises for example Gasterophilus (Gastrophilus spp.), Genus Stomoxys (Stomoxys spp.), Trichodectes (Trichodectes spp.), Rhodnius (Rhodnius spp.), ctenocephalides canis (Ctenocephalides canis), Cimex lecturius, ctenocephalides felis (Ctenocephalidesfelis) and lucilia cuprina (Lucilia cuprina);

Acarid, comprises that for example Ornithodoros (Ornithodoros spp.), hard tick belong to and Boophilus (Boophilus spp.) (being now called Rh (Rhipicephalus spp.)).

As mentioned before, in veterinary applications,, in veterinary field, active compound of the present invention is to zooparasite, and---particularly vermin or endoparasite---has activity.Term endoparasite comprises particularly worm, for example tapeworm, nematode or fluke; And protozoon, for example coccidia.Vermin conventionally and be preferably arthropods, particularly insect, as fly (terebra and lick suction), tachinid larva, sucking louse, food hair lice, flea etc.; Or acarid, for example tick, as hard tick or soft ticks, or acarian, such as itch mite, harvest mite, bird mite etc.

These parasites comprise:

Anoplura (Anoplurida), for example, Haematopinus (Haematopinus spp.), Linognathus (Linognathus spp.), lice belong to (Pediculus spp.), Phtirus spp., pipe lice belongs to (Solenopotes spp.), specific examples has: sour jujube jaw lice (Linognathus setosus), Linognathus vituli (Linognathus vituli), sheep jaw lice (Linognathus ovillus), Linognathusoviformis, foot jaw lice (Linognathus pedalis), goat jaw lice (Linognathusstenopsis), giant's haematopinus asina (Haematopinus asini macrocephalus), haematopinus eurysternus (Haematopinus eurysternus), haematopinus suis (Haematopinus suis), head louse (Pediculus humanus capitis), body louse (Pediculus humanus corporis), grape phylloxera (Phylloera vastatrix), crab louse (Phthirus pubis), solenoptes capillatus (Solenopotes capillatus),

Mallophaga (Mallophagida) and Amblycera (suborder Amblycerina) and thin angle suborder (suborder Ischnocerina), for example, hair Trichodectes (Trimenoponspp.), Menopon (Menopon spp.), huge Trichodectes (Trinoton spp.), Bovicola (Bovicola spp.), Werneckiella spp., Lepikentron spp., Damalinia (Damalina spp.), Trichodectes (Trichodectes spp.), Felicola (Felicolaspp.); Specific examples has: ox hair lice (Bovicola bovis), wool lice (Bovicola ovis), Bovicola limbata, Damalinia bovis (Damalina bovis), dog hair lice (Trichodectescanis), cat poultry louse (Felicola subrostratus), goathair lice (Bovicola caprae), Lepikentron ovis, sting lice (Werneckiella equi);

Diptera and Nemocera (suborder Nematocerina) and Brachycera (suborder Brachycerina), for example, Aedes (Aedes spp.), Anopheles (Anophelesspp.), Culex (Culex spp.), Simulium (Simulium spp.), Eusimulium (Eusimuliumspp.), owl midge (Phlebotomus spp.), Lutzomyia (Lutzomyia spp.), Bitting midge (Culicoides spp.), Chrysops (Chrysops spp.), Odogmia (Odagmiaspp.), Wilhelmia spp., Hybomitra (Hybomitra spp.), Atylotus (Atylotusspp.), Gadfly (Tabanus spp.), Chrysozona (Haematopota spp.), Philipomyiaspp., honeybee Hippobosca (Braula spp.), Musca (Musca spp.), Hydrotaea (Hydrotaeaspp.), Genus Stomoxys (Stomoxys spp.), Haematobia (Haematobia spp.), fly does not belong to (Morellia spp.), Fannia (Fannia spp.), Glossina (Glossina spp.), Calliphora (Calliphora spp.), Lucilia (Lucilia spp.), Carysomyia (Chrysomyiaspp.), Wohlfahrtia (Wohlfahrtia spp.), Sarcophaga (Sarcophaga spp.), Oestrus (Oestrus spp.), Hypoderma (Hypoderma spp.), Gasterophilus (Gasterophilusspp.), Hippobosca (Hippobosca spp.), Lipoptena (Lipoptena spp.), Melophagus (Melophagus spp.), Rhinoestrus (Rhinoestrus spp.), large uranotaenia (Tipulaspp.), specific examples has: Aedes aegypti (Aedes aegypti), Aedes albopictus (Aedesalbopictus), aedes taeniorhynchus (Aedes taeniorhynchus), anopheles costalis (Anophelesgambiae), anopheles maculipennis (Anopheles maculipennis), calliphora erythrocephala (Calliphoraerythrocephala), great number fiber crops horseflys (Chrysozona pluvialis), five band culex pipiens pollens (Culexquinquefasciatus), northern house (Culex pipiens), ring beak culex (Culex tarsalis), Fannia canicularis (Fannia canicularis), flesh fly (Sarcophaga carnaria), tatukira (Stomoxys calcitrans), Europe daddy-longlegs, lucilia cuprina, lucilia sericata (Lucilia sericata), Simulium reptans (Simulium reptans), quiet food sand fly (Phlebotomus papatasi), phlebotomus lognipes (Phlebotomus longipalpis), magnificent short buffalo gnat (Odagmia ornata), Wilhelmiaequina, reddish tone is detested buffalo gnat (Boophthora erythrocephala), many sound horsefly (Tabanusbromius), noctuid horsefly (Tabanus spodopterus), tabanus atratus (Tabanus atratus), Tabanus sudeticus, Gooch knurl horsefly (Hybomitra ciurea), chrysops cecutiens (Chrysopscaecutiens), chrysops relictus (Chrysops relictus), great number fiber crops horseflys (Haematopotapluvialis), Haematopota italica, face fly (Musca autumnalis), housefly, Haematobia irritans irritans, Haematobia irritans exigua, thorn Haematobia irritans (Haematobia stimulans), Hydrotaea irritans, hickie tooth thigh fly (Hydrotaeaalbipuncta), Chrysomya chloropyga, maggot disease gold fly (Chrysomya bezziana), Oestrus ovis (Oestrus ovis), bomb fly (Hypoderma bovis), heel fly (Hypodermalineatum), Przhevalskiana silenus, people torsalo (Dermatobia hominis), sheep tick (Melophagus ovinus), Lipoptena capreoli, Lipoptena cervi, Hippobosca variegata, horse louse fly (Hippobosca equina), Gasterophilus intestinalis (Gasterophilus intestinalis), Gasterophilus haemorrhoidalis (Gasterophilus haemorroidalis), naked joint stomach fly (Gasterophilus inermis), gasterophilus nasalis (Gasterophilus nasalis), black angle stomach fly (Gasterophilus nigricornis), gastrophilus pecorum (Gasterophiluspecorum), honeybee hippoboscid (Braula coeca),

Siphonaptera (Siphonapterida), for example, flea belongs to (Pulex spp.), Ctenocephalus (Ctenocephalides spp.), Dermatophilus (Tunga spp.), objective flea genus (Xenopsyllaspp.), Ceratophyllus (Ceratophyllus spp.); Specific examples has: ctenocephalides canis (Ctenocephalides canis), ctenocephalides felis, Pulex irritans (Pulex irritans), chigo (Tunga penetrans), Xanthopsyllacheopis;

Heteroptera (Heteropterida), for example, Cimex (Cimex spp.), Triatoma (Triatoma spp.), Rhodnius (Rhodnius spp.), Triatoma (Panstrongylusspp.);

Blattodea (Blattarida), for example, oriental cockroach (Blatta orientalis), periplaneta americana (Periplaneta americana), blatta germanica (Blattela germanica), Supella (Supella spp.) (for example Suppella longipalpa);

Acarian (Acari or Acarina) subclass and rear valve order (Metastigmate) and Mesostigmata (Mesostigmata), for example, Argas, Ornithodoros (Ornithodorus spp.), residual beak tick belongs to (Otobius spp.), hard tick belongs to, Amblyomma, Rh (Boophilus) (Rhipicephalus (Boophilus) spp.), Dermacentor (Dermacentor spp.), Haemophysalis spp., Hyalomma (Hyalomma spp.), Dermanyssus (Dermanyssusspp.), Rh (belonging to originally of many hosts tick), Ornithonyssus (Ornithonyssus spp.), Pneumonyssus (Pneumonyssus spp.), sting sharp mite and belong to (Raillietia spp.), Pneumonyssusspp., chest thorn mite belongs to (Sternostoma spp.), Vespacarus (Varroa spp.), Acarapisspp., specific examples has: adobe tick (Argas persicus), stick up edge sharp-edged tick (Argasreflexus), tampan tick (Ornithodorus moubata), Otobius megnini, small fan head tick (boophilus microplus) (Rhipicephalus (Boophilus) microplus), colour killing fan head tick (boophilus decoloratus) (Rhipicephalus (Boophilus) decoloratus), tool ring fan head tick (Boophilus annulatus) (Rhipicephalus (Boophilus) annulatus), there is square fan head tick (having square ox tick) (Rhipicephalus (Boophilus) calceratus), hyalomma anatolicum (Hyalomma anatolicum), Hyalomma aegypticum (Hyalomma aegypticum), edge glass eye tick (Hyalomma marginatum), Hyalomma transiens, rhipicephalus evertsi (Rhipicephalus evertsi), castor bean tick (Ixodes ricinus), the hard tick of hexagonal (Ixodeshexagonus), the hard tick in open country (Ixodes canisuga), ixodes pilosus (Ixodes pilosus), ixodes rubicundus (Ixodes rubicundus), ixodes scapularis (Ixodes scapularis), ixodes holocyclus (Ixodes holocyclus), haemaphysalis conicinna (Haemaphysalis concinna), Haemaphysalis punctata (Haemaphysalis punctata), Haemaphysalis cinnabarina, Haemaphysalis otophila, haemaphysalis leachi (Haemaphysalis leachi), haemaphysalis longicornis (Haemaphysalis longicorni), dermacentor marginatus (Dermacentor marginatus), dermacentor reticulatus (Dermacentor reticulatus), Dermacentor pictus, Dermacentoralbipictus, Dermacentor andersoni (Dermacentor andersoni), Dermacentor variabilis (Dermacentorvariabilis), Mauritius's glass eye tick (Hyalomma mauritanicum), brown dog tick (Rhipicephalus sanguineus), scrotiform fan head tick (Rhipicephalus bursa), rhipicephalus appendiculatus (Rhipicephalus appendiculatus), rhinpicephalus capensis (Rhipicephalus capensis), R.turanicus (Rhipicephalus turanicus), Rhipicephalus zambeziensis, lone star tick (Amblyomma americanum), illuminated flower tick (Amblyomma variegatum, there is spot flower tick (Amblyommamaculatum), Hebrew spends tick (Amblyomma hebraeum), card prolongs colored tick (Amblyomma cajennense), Dermanyssus gallinae (Dermanyssus gallinae), capsule fowl thorn mite (Ornithonyssus bursa), northern fowl mite (Ornithonyssus sylviarum), varoa mite (Varroa jacobsoni),

Axle Acarina (Actinedida) (front valve suborder (Prostigmata)) and flour mite order (Acaridida) (Astigmata (Astigmata)), for example, honeybee shield mite belongs to (Acarapisspp.), Cheyletiella (Cheyletiella spp.), Ornithocheyletia (Ornithocheyletia spp.), Myobia (Myobia spp.), Psorergates (Psorergates spp.), Demodex (Demodexspp.), Trombidium (Trombicula spp.), Listrophorus spp., Tyroglyphus (Acarusspp.), Tyrophagus (Tyrophagus spp.), Caloglyphus (Caloglyphus spp.), under neck, mite belongs to (Hypodectes spp.), wing mite belongs to (Pterolichus spp.), Psoroptes (Psoroptes spp.), Chorioptes (Chorioptes spp.), ear itch mite belongs to (Otodectes spp.), itch mite belongs to (Sarcoptes spp.), Notoedres (Notoedres spp.), lump mite belongs to (Knemidocoptes spp.), Cytodites (Cytodites spp.), Laminosioptes (Laminosioptes spp.), specific examples has: Ya Shi Ji chela mite (Cheyletiella yasguri), cheyletiella blakei (Cheyletiella blakei), demodicidosis (Demodex canis), ox demodicid mite (Demodex bovis), sheep demodicid mite (Demodex ovis), Demodex caprae (Demodex caprae), horse demodicid mite (Demodex equi), Demodex caballi, pig demodicid mite (Demodex suis), Neotrombicula autumnalis, Neotrombiculadesaleri,

xerothermobia, bete rouge (Trombiculaakamushi), dog ear mite (Otodectes cynotis), cat scab mite (Notoedres cati), sarcoptes canis (Sarcoptis canis), Sarcoptes bovis (Sarcoptes bovis), sheep itch mite (Sarcoptesovis), goat itch mite (Sarcoptes rupicaprae (=S.caprae)), sarcoptes equi (Sarcoptesequi), Sarcoptes suis (Sarcoptes suis), sheep scabies mite (Psoroptes ovis), rabbit scabies mite (Psoroptes cuniculi), horse scabies mite (Psoroptes equi), psoroptes bovis (Chorioptesbovis), Psoergates ovis, Pneumonyssoidic Mange, dog Bi Jie Insect (Pneumonyssoides caninum), Wu Shi honeybee tarsonemid mite (Acarapis woodi).

Active compound of the present invention is also suitable for arthropods, worm and the protozoon of control invasion and attack animal.Preferably control arthropods.Particularly preferably prevent and treat insect.Comparably, particularly preferably prevent and treat mite.

Parasitic animal be can process to prevent and treat and bird, insect and particularly Mammals comprised.Animal comprises agriculture domestic animal, for example ox, sheep, goat, horse, pig, donkey, camel, buffalo, rabbit, family chicken, furbearer, turkey, duck, goose, cultivation fish, honeybee.In addition animal also comprises domestic animal---also referred to as companion animals---and for example dog, cat, ferret, cage bird, aquarium fish, Reptilia, and alleged laboratory animal, for example hamster, cavy, rat and mouse.

By preventing and treating these arthropodss, worm and/or protozoon, be intended to reduce the death of host animal, and improve its (meat, milk, hair, skin, egg, honey etc.) productivity and healthy state, so that can the application of the invention active compound and make animal rearing more economical and easier.

For example, wish prevention or interrupt parasite to absorb host's blood (working as where applicable).In addition, control parasite can contribute to prevent the propagation of infectious agent.

The term relevant with veterinary applications used herein " control " means active compound can make each parasite be reduced to harmless level at the sickness rate infecting in described parasitic animal effectively.More specifically, " control " used herein mean active compound and can effectively kill each parasite, suppress its growth or suppress its breeding.

When active compound of the present invention is used as sterilant, can be made into conventional formulation form.Described dosage form for example comprises, solution, emulsion, wettable powder, water dispersible granules, suspension agent, pulvis, foaming agent, paste, tablet, granule, aerosol, natural and synthetics, microcapsule, coating agent for seed, the preparation (combustion unit comprises for example stifling and sootiness cylinder, tank and coil pipe (fumigationand smoking cartridges, cans and coils)) using with combustion unit (burning device) and the cold mist agent of UVL[through active compound dipping, thermal fog].

These preparations can be prepared according to currently known methods.For example, they can be by mixing active compound with weighting agent, mix with liquid diluent or carrier, liquefied gas diluent or carrier, solid diluent or carrier, and optionally use tensio-active agent, be i.e. emulsifying agent and/or dispersion agent and/or whipping agent and make.These preparations in suitable equipment previously prepared or using before or in application directly preparation.

What be suitable for use as auxiliary agent is the material that is suitable for giving compound and composition itself and/or preparation therefrom (for example spray liquor, seed dressing) specified property---for example some technical feature and/or particular organisms performance---.Typical suitable auxiliary agent has: weighting agent, solvent or thinner and carrier.

Suitable weighting agent has for example water, polarity and nonpolar organic chemistry liquid, organic chemistry liquid as following kind: aromatic hydrocarbon and non-aromatic hydrocarbon (for example paraffin, alkylbenzene, alkylnaphthalene, chlorobenzene), alcohol and polyvalent alcohol are (if suitable, it also can be substituted, etherificate and/or esterification), ketone (for example acetone, pimelinketone), ester (comprising fat and oil) and (gathering) ether, unsubstituted and substituted amine, acid amides, lactan (for example N-alkyl pyrrolidone) and lactone, sulfone and sulfoxide (for example methyl-sulphoxide).

If weighting agent used is water, for example also can use organic solvent as solubility promoter.

Suitable solid carrier for example has, ammonium salt, and pulverize natural mineral as kaolin, clay, talcum, chalk, quartz, attapulgite, montmorillonite or diatomite, and pulverize synthetic mineral as finely divided silicon-dioxide, aluminum oxide and silicate; The solid carrier that is applicable to granule has: for example pulverize the also natural rock of classification, as calcite, marble, float stone, sepiolite and rhombspar; And synthetic inorganic and organic powder particles; And for example particle of paper, sawdust, coconut husk, corn cob and tobacco stem of organism; Suitable emulsifying agent and/or whipping agent have: for example nonionic and anionic emulsifier, as polyoxyethylene fatty acid ester, polyoxyethylene aliphatic alcohol ether, as alkylaryl polyglycol ether, alkylsulfonate, alkyl-sulphate, arylsulphonate, and protein hydrolyzate; Suitable dispersion agent has nonionic and/or ionic species, the material of for example following classification: alcohol-POE-and/or alcohol-POP ether, acid and/or POP-POE ester, alkylaryl and/or POP-POE ether, fat-and/or POP-POE adducts, POE-and/or POP-polyol derivative, POE-and/or POP-Sorbitol Powder or-sucrose adducts, alkyl or aryl sulfuric ester, alkyl or aryl sulphonate, and alkyl or aryl phosphoric acid ester, or corresponding PO-ether adducts.In addition suitable oligopolymer or polymkeric substance are, for example by vinyl monomer, by vinylformic acid, by independent or with the oligopolymer or the polymkeric substance that for example (gather) EO that alcohol or (gathering) amine combines and/or PO and obtain.Also can use the adducts of Mierocrystalline cellulose, aromatics and/or the aliphatic sulfonic acid of xylogen and sulfonic acid thereof, unmodified and modification and they and formaldehyde.

Liquid diluent, solvent or carrier for example comprise, aromatic hydrocarbon (for example dimethylbenzene, toluene, alkylnaphthalene), chlorinated aromatics or chlorination aliphatic hydrocrbon (for example chlorobenzene, vinylchlorid, methylene dichloride), aliphatic hydrocrbon [for example hexanaphthene or paraffin (for example mineral oil fractions or vegetables oil)], alcohol (for example butanols, ethylene glycol and their ether or ester), ketone (for example acetone, methylethylketone, methyl iso-butyl ketone (MIBK), pimelinketone), intensive polar solvent (for example dimethyl formamide, methyl-sulphoxide); And water.

Liquefied gas diluent or carrier is included in the material existing with gas under normal temperature and normal pressure, and comprises for example aerosol spray, as furans, propane, nitrogen, carbonic acid gas and halohydrocarbon.

Suitable thinner comprises the natural mineral (for example kaolin, clay, talcum, chalk, quartz, attapulgite, montmorillonite or diatomite) of for example pulverizing and the synthetic mineral (for example finely divided silicic acid, aluminum oxide, silicate) of pulverizing.

The solid carrier that is applicable to granule for example comprises, pulverize the rock (for example calcite, marble, float stone, sepiolite, rhombspar) of also classification, synthetic inorganic or organic powder particles, and the fine particle of organism (for example sawdust, coconut husk, corn cob, tobacco stem).

Emulsifying agent and/or whipping agent for example comprise, for example nonionic or anionic emulsifier [for example polyoxyethylene fatty acid ester, polyoxyethylene aliphatic alcohol ether (for example alkylaryl polyglycol ether), alkylsulfonate, alkyl-sulphate, arylsulphonate], and albumin hydrolysate.

Dispersion agent for example comprises, lignin sulfite waste lye and methylcellulose gum.

In preparation (pulvis, granule, emulsion), also can use tackiness agent, described tackiness agent for example comprises, carboxymethyl cellulose and natural or synthetic polymer (for example Sudan Gum-arabic, polyvinyl alcohol, polyvinyl acetate).

Can use tinting material, and it for example comprises, mineral dye (for example ferric oxide, titanium oxide, Prussian blue), organic dye (for example alizarine dyestuff, azoic dyestuff or metal phthalocyanine dyestuff), and trace element (for example molysite, manganese salt, boron salt, mantoquita, cobalt salt, molybdenum salt and zinc salt).

Other available auxiliary agents have spices, optional mineral oil or vegetables oil, wax and nutrient substance (comprising trace nutrient) through modification, for example molysite, manganese salt, boron salt, mantoquita, cobalt salt, molybdenum salt and zinc salt.

Also can there is stablizer, the medicament of for example cryostatic stabilization agent, sanitas, antioxidant, photostabilizer or other improvement chemistry and/or physical stability.

Normally, preparation of the present invention can be in 0.1 to 95 % by weight, preferably the amount within the scope of 0.5 to 90 % by weight contains above-mentioned active ingredient.

Active compound of the present invention can be combined with other active compounds and exist, and described other active compounds are insecticide, poison bait agent, bactericide, miticide, nematocides, mycocide, growth regulator, the weedicide of dosage form that for example can be commercial or the administration form prepared by described preparation.Aforementioned insecticide for example comprises, organophosphorus medicament, carbamate medicament, carboxylicesters medicament, chlorinated hydrocarbon type medicament, the insect killing substance of being prepared by microorganism.

In addition, active compound of the present invention can be used as with the mix reagent of synergistic agent and exists, and this class preparation and administration form comprise preparation and administration form that can be commercial.Described synergistic agent itself is without having activity, but effect that can enhanced activity compound.

The content of the active compound of the present invention of administration form that can be commercial can change in wide scope.

The concentration of the active compound of the present invention of using can be in the scope of 0.0000001-100 % by weight, preferably in the scope of 0.00001-1 % by weight.

The usual manner that the compounds of this invention can be suitable for its administration form uses.It should be understood that the compounds of this invention also can be present in the composition containing other compositions, for example auxiliary agent or activeconstituents.Technician can select a kind of suitable composition in composition described herein and known in the art, that estimate to strengthen the performance that is considered to be conducive to predetermined application and use.

All plants and plant parts all can be according to processing of the present invention.In the present invention, the implication of plant is interpreted as all plants and plant population, wild plant that for example need and unwanted or crop plants (comprising naturally occurring crop plants).Crop plants can be can be by conventional plant breeding and optimum seeking method or by biotechnology and genetic engineering method or the plant that obtains by the combination of preceding method, and described plant comprises transgenic plant and comprises the plant cultivars that is subject to plant breeder to weigh (plantbreeders ' rights) protection or is not subject to its protection.The implication of plant parts is interpreted as all grounds and underground position and the plant organ of plant, for example bud, leaf, Hua Hegen, and the example that can mention has leaf, needle, stem, dry, flower, sporophore, fruit, seed, root, stem tuber and rhizome.Plant parts also comprises harvested material, and asexual and sexual propagation thing, for example, transplant, stem tuber, rhizome, branch and seed.

The processing of with active compound, plant and plant parts being carried out according to the present invention, by conventional treatment method directly or compound effects is carried out in its environment, habitat or storage space, described conventional treatment method for example floods, spraying, evaporation, atomization, broadcast sowing, smear, inject, and, for breeding thing, particularly, for seed, also can use one or more layers dressing.

As mentioned above, can process all plants and position thereof according to the present invention.In a kind of preferred embodiment, process wild plant kind and plant cultivars, or by for example hybridization of conventional Biology Breeding method or protoplast fusion and the plant species and the plant cultivars that obtain, and their position.In another kind of preferred embodiment, if processed by gene engineering method---suitable, combine with ordinary method---and transgenic plant and plant cultivars (genetically modified organisms) and the position thereof of acquisition.Explain as above at term " position ", " position of plant " and " plant parts ".

The plant of particularly preferably, processing according to the present invention is the commercially available plant cultivars that obtains or using separately.The implication of plant cultivars is interpreted as the plant with new features (" feature ") being obtained by conventional breeding, mutagenesis or recombinant DNA technology.They can be cultivar, biotype or genotype.

According to plant variety or plant cultivars, its plantation place and growth conditions (soil, weather, vegetative growth phase, nutrition (diet)), processing of the present invention also can produce super adding and (" working in coordination with ") effect.Can obtain thus the effect that exceedes as follows actual desired, for example reduce material and the rate of application of composition that can use according to the present invention and/or widen its activity profile and/or improve its activity, improve plant-growth, improve high temperature or cold tolerance, raising to arid or the tolerance to water or soil salt content, improve Flowering quality, simpler and easy, the accelerates maturing of making to gather, raising are gathered productive rate, improve the quality of the product of gathering and/or improve its nutritive value, improve package stability and/or its processibility of the product of gathering.

Transgenic plant or the plant cultivars (obtaining by genetic engineering) of preferably treating the processing according to the present invention comprise all plants of having accepted genetic material by genetic modification, and described genetic material has given described plant advantageous particularly, useful feature.The example of described feature is improved plant-growth, improves high temperature or cold tolerance, raising to arid or the tolerance to water or soil salt content, improve Flowering quality, simpler and easy, the accelerates maturing of making to gather, raising are gathered productive rate, improve the quality of the product of gathering and/or improve its nutritive value, improve package stability and/or its processing characteristics of the product of gathering.Further other examples of ben described feature are improved the resistibility of plant to animal and microorganism nuisance, the for example resistibility to insect, acarid, plant pathogenic fungi, bacterium and/or virus, and improve the tolerance of plant to some weeding active compound.The example of the transgenic plant that can mention is important crop plants, such as grain (wheat, rice), corn, soybean, potato, beet, tomato, pea and other vegetable varieties, cotton, tobacco, rape (oilseed rape) and fruit plant (fruit is apple, pears, citrus fruit and grape), ben is corn, soybean, potato, cotton, tobacco and rape.The ben toxin being characterized as by forming in plant materials, the toxin particularly for example, being formed in plant materials by the genetic material (gene C ryIA (a), CryIA (b), CryIA (c), CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CryIF and combination thereof) of Bacillus thuringiensis (Bacillus thurigiensis), improves the resistibility of plant (hereinafter referred to as " Bt plant ") to insect, arachnid, nematode and slug and snail.Also ben being characterized as by systemic acquired resistance (SAR), systemin, phytoalexin, releaser (elicitor) and resistant gene and corresponding marking protein and toxin improved the resistibility of plant to fungi, bacterium and virus.In addition ben being characterized as improved the tolerance of plant to some weeding active compound, for example tolerance to imidazolone type, sulfonylurea, glyphosate (glyphosate) or careless fourth phosphine (phosphinotricin) (for example " PAT " gene).The gene of giving described required feature also can mutually combine and exist in transgenic plant body.The example of " the Bt plant " that can mention has commercially available trade name to be

(for example corn, cotton, soybean), (for example corn),

(for example corn),

(cotton),

(cotton) and corn variety, cotton variety, soybean varieties and the Potato Cultivars of (potato).The example of the herbicide tolerant plants that can mention has commercially available trade name to be

(thering is glyphosate tolerant, for example corn, cotton, soybean),

(thering is careless fourth phosphine tolerance, for example rape),

(thering is imidazolinone-tolerant) and

corn variety, cotton variety and the soybean varieties of (thering is sulfonylurea tolerance, for example corn).The plant with Herbicid resistant (with the plant of conventional herbicide tolerant mode breeding) that can mention comprises that name is called

the commercially available mutation of (for example corn).Certainly, above narration is also applicable to have the plant cultivars of described gene expression characteristics or gene expression characteristics to be developed, and described plant cultivars will be developed and/or go on the market in future.

Listed plant can be processed according to the present invention in the particularly advantageous mode of one with the compounds of this invention or composition.The preferable range of above-mentioned active compound or composition is also applicable to the processing of described plant.Lay special stress on is with the compound of specifically mentioning in this specification sheets or compositions-treated plant.

Also find that the compounds of this invention also has strong insecticidal action to the insect that damages Industrial materials.

Can be used as example preferably but mention without limitation following insect:

Beetle, for example North America house longhorn beetle (Hylotrupes bajulus), Chlorophorus pilosis, furniture death watch beetle (Anobium punctatum), report dead death watch beetle (Xestobium rufovillosum), Ptilinus pectinicornis (Ptilinus pecticornis), Dendrobium pertinex, pine death watch beetle (Ernobius mollis), Priobium carpini, Lyctus brunneus Stephens (Lyctus brunneus), Africa powder moth (Lyctus africanus), south powder moth (Lyctus planicollis), quercitron moth (Lyctus linearis), pubescence powder moth (Lyctus pubescens), Trogoxylon aequale, minthea rugicollis (Minthes rugicollis), material bark beetle kind (Xyleborus spec.), Tryptodendron spec., coffee black long moth-eaten (Apate monachus), Mongolian oak long moth-eaten (Bostrychuscapucins), brown different wing long moth-eaten (Heterobostrychus brunneus), long moth-eaten plant (the Sinoxylon spec.) of sour jujube, dinoderus minutus (Dinoderus minutus),

Hymenopteran (Hymenopteron), for example large wood wasp (Sirexjuvencus), the large wood wasp of fir (Urocerus gigas), safe wood wasp (Urocerus gigas taignus), the Urocerusaugur of strengthening;

Termite, for example European kalotermitid (Kalotermes flavicollis), a fiber crops heap sand termite (Cryptotermes brevis), the ash different termite of point (Heterotermes indicola), American-European reticulitermes flavipe (Reticulitermes flavipes), Sang Te reticulitermes flavipe (Reticulitermessantonensis), southern Europe reticulate pattern termite (Reticulitermes lucifugus), Darwin Australia termite (Mastotermes darwiniensis), the ancient termite in Nevada (Zootermopsisnevadensis), Coptotermes formosanus Shtrari． (Coptotermes formosanus),

Moth (Bristletail), for example silverfish.

The implication of the Industrial materials in the present invention is interpreted as non-living body material, for example, and preferably plastics, tackiness agent, sizing material, paper and cardboard, leather, timber, and through timber products and the coating composition of processing.

If suitable, describedly also can contain other sterilants with composition, also can contain one or more sterilant and if suitable.

About other available additives, can be referring to above-mentioned sterilant and sterilant.

The compounds of this invention can be used for object, particularly hull, sieve, net, buildings, harbour and the signalling system that protection contacts with salt water or slightly salty equally, with dirt-proof.

In addition, the compounds of this invention can individually or be combined with other active compounds and as stain control agent.

In family expenses, health and storage product protection; described active compound is also suitable for preventing and treating the animal nuisance of finding in enclosed space; particularly insect, arachnid and acarid, described enclosed space is residence, factory floor, office, compartment etc. such as.They can combine and prevent and treat described insect for family expenses desinsection product individually or with other active compounds and auxiliary agent.They have activity to sensitivity and resistance species and to whole etap.Described insect comprises:

Scorpionida (Scorpionidea), for example yellow scorpion in Mediterranean Sea (Buthus occitanus).

Acarina, for example adobe tick (Argas persicus), argas reflexus (Argasreflexus), tongue mite subspecies (Bryobia ssp.), Dermanyssus gallinae, sweet mite (Glyciphagusdomesticus) is had a liking for by family, tampan tick (Ornithodorus moubat), brown dog tick (Rhipicephalus sanguineus), eutrombicula alfreddugesi (Trombicula alfreddugesi), Neutrombicula autumnalis, spy has a liking for skin mite (Dermatophagoidespteronissimus), method is had a liking for skin mite (Dermatophagoides forinae).

Araneida (Araneae), for example catching bird spider (Aviculariidae), circle spider (Araneidae).

Opiliones (Opiliones), for example chelifer (Pseudoscorpiones chelifer), Pseudoscorpiones cheiridium, long abnormal blind spider (Opiliones phalangium).

Isopoda, for example comb beach louse, ball pillworm.

Doubly sufficient order, for example Blaniulus guttulatus, mountain cricket Eimeria (Polydesmus spp.).

Lip foot order, for example DIWUGONG belongs to.

Silverfish order (Zygentoma), for example comb silverfish belongs to (Ctenolepisma spp.), silverfish, robber fireworm (Lepismodes inquilinus).

Blattodea, for example oriental cockroach, blatta germanica, Asia Lian (Blattella asahinai), leucophaea maderae, angle abdomen Lian belong to (Panchlora spp.), wooden Lian belongs to (Parcoblatta spp.), Australian cockroach (Periplaneta australasiae), periplaneta americana, large brown large Lian (Periplanetabrunnea), smoke Perilpaneta americana (Periplaneta fuliginosa), brown belt blattaria (Supellalongipalpa).

Jump order (Saltatoria), for example Xi of family.

Dermaptera, for example European earwig.

Isoptera, for example kalotermitid belongs to (Kalotermes spp.), Reticulitermes.

Corrodentia (Psocoptera), for example Lepinatus spp., powder corrodent belong to (Liposcelisspp.).

Coleoptera (Coleptera), for example Anthrenus, the moth-eaten genus of fur, khapra beetle genus, long an ostomatid (Latheticus oryzae), hidden instep cuckoo Eimeria (Necrobia spp.), Ptinus, lesser grain borer, grain weevil (Sitophilus granarius), rice weevil (Sitophilus oryzae), sitophilus zea-mais (Sitophilus zeamais), Stegobium paniceum (Stegobium paniceum).

Diptera, for example Aedes aegypti (Aedes aegypti), Aedes albopictus (Aedesalbopictus), aedes taeniorhynchus (Aedes taeniorhynchus), Anopheles, calliphora erythrocephala, great number fiber crops horseflys (Chrysozona pluvialis), five band culex pipiens pollens (Culexquinquefasciatus), northern house (Culex pipiens), ring beak culex (Culextarsalis), Drosophila (Drosophila spp.), Fannia canicularis (Fannia canicularis), housefly, owl midge, flesh fly (Sarcophaga carnaria), Simulium, tatukira (Stomoxyscalcitrans), Europe daddy-longlegs.

Lepidopteran, for example lesser wax-moth (Achroia grisella), greater wax moth, Indian meal moth (Plodiainterpunctella), stopper rain moth (Tinea cloacella), bag rain moth, curtain rain moth.

Siphonaptera, for example ctenocephalides canis, ctenocephalides felis, Pulex irritans (Pulex irritans), chigo (Tunga penetrans), Xanthopsyllacheopis.

Hymenoptera, for example, blazon hunchbacked ant (Camponotus herculeanus), black smelly ant (Lasius fuliginosus), black ant (Lasius niger), Lasius umbratus, MonomoriumMayr, Paravespula spp., Pavement Ant (Tetramorium caespitum).

Anoplura (Anoplura), for example head louse (Pediculus humanus capitis), body louse (Pediculus humanus corporis), Pemphigus spp., Phylloeravastatrix, crab louse (Phthirus pubis).

Heteroptera, for example cimex hemipterus (Cimex hemipterus), bed bug (Cimexlectularius), phodnius prolixus (Rhodinus prolixus), invasion triatomid (Triatomainfestans).

In family expenses field of pesticides, active compound that can be suitable with other is combined with and especially preferred combination use, and described suitable active compound is phosphoric acid ester, amino formate, pyrethroid, anabasine, growth regulator or other known insecticides class active compounds for example.

The compounds of this invention or composition---are preferably its suitable administration form---and can be used in following product: aerosol, spray product with no pressure, for example pump spraying and atomizer spray, automatic atomising system, propellant, foaming agent, gelifying agent; There is the evaporation agent product of the evaporating plate of being made by Mierocrystalline cellulose or polymkeric substance, liquid evaporation agent, gel and film evaporation agent, the evaporation agent of impeller driven, unpowered or passive vapo(u)rization system; Catch moth paper, catch moth bag and catch moth glue, be used in the bait or Poison bait station (bait station) shed as granule or powder agent.

Compound of the present invention or composition are particularly suitable for processing seed.The major part to the crop plants infringement being caused by insect when during seed storage, seed is attacked and planting seed during plant germination and after just having germinateed, just occurred after entering in soil.This stage is crucial especially because in growth the root of plant and bud responsive especially, even if minor harm also can cause the death of whole strain plant.Therefore by using proper combination thing protection seed and germination plant to there is great especially meaning.

By processing plant seed, to carry out pest control be long-term known and be the theme of updating.But the processing of seed is with a series of problems that can not always solve in a kind of gratifying mode.Therefore, like this some are used for protecting the method for seed and germination plant to need exploitation, the method without after sowing or plant emerge and use in addition crop protection agents afterwards.In addition wish to optimize the consumption of active compound, to provide to seed and germination plant the maximum protection of avoiding insect invasion and attack, and active compound used can not damage plant itself.Particularly, the method for processing seed also should be considered to reach the best protection to seed and germination plant to use the crop protection agents of minimum by the intrinsic insecticidal properties of transgenic plant.

Therefore the present invention is also particularly related to a kind of the application of the invention compositions-treated seed and protects seed and germination plant to avoid the method for insect invasion and attack.The invention still further relates to the present composition avoids suffering insect invasion and attack with the plant of protection seed and generation purposes for the treatment of seed.In addition, thus the invention still further relates to and to process the seed that obtains protection and avoid suffering insect invasion and attack with the present composition.

One of advantage of the present invention is, the peculiar internal absorption characteristic of the present composition means the invasion and attack that post avoids insect of planting that generate after not only protecting seed itself but also protection to emerge with these compositions-treated seeds.By this method, can exempt at seeding time or the processing immediately to crop soon thereafter.

In addition, must be considered to advantageously, the compounds of this invention or composition also can be used in particular for transgenic seed, and the plant being generated by this seed can be expressed the albumen of opposing insect.By process this class seed with the present composition, some insect can only be prevented and treated by the expression of for example insecticidal proteins, and the present composition also protects seed to avoid infringement in addition.

The compounds of this invention or composition are suitable for the seed of any plant variety using in agricultural, greenhouse, forest or gardening of having mentioned above protection.Especially, the form of described seed is: the seed of corn, peanut, Canadian rape, rape, opium poppy, soybean, cotton, beet (for example sugar beet and fodder beet), rice, jowar and grain, wheat, barley, oat, rye, Sunflower Receptacle, tobacco, potato or vegetables (for example tomato, Caulis et Folium Brassicae capitatae plant).The present composition is suitable for processing the seed of above mentioned fruit plant and vegetables equally.The present composition is also suitable for processing the seed of fruit plant referred to above and vegetables.The processing particularly important of corn, soybean, cotton, wheat and Canadian rape or brassica seed.

As mentioned above, process also particularly important of transgenic seed with the present composition.The form of described seed is the plant seed that conventionally contains at least one heterologous gene, and this heterologous gene domination particularly has the expression of the polypeptide of insecticidal properties.Herein, the heterologous gene of transgenic seed can come from for example genus bacillus of microorganism (Bacillus), root nodule bacterium (Rhizobium), pseudomonas (Pseudomonas), Serratia (Serratia), wood mould (Trichoderma), Clavibacter, glomus (Glomus) or glutinous broom mould (Gliocladium).The present invention is particularly suitable for processing the transgenic seed that contains at least one and come from bacillus and its gene product and show opposing European corn borer (European corn borer) and/or the active heterologous gene of corn rootworm (corn rootworm).Particularly preferably come from the heterologous gene of Bacillus thuringiensis.

In the present invention, the present composition is applied to seed individually or with suitable formulations.Preferably, under a kind of steady state of the infringement during being enough to avoid to process, process seed.Normally, seed can gather and sow between random time point process.Cob, shell, stem, epidermis, hair or pulp have been isolated and removed to normally used seed from plant.

Process kind of a period of the day from 11 p.m. to 1 a.m, conventionally must be noted that the amount of the present composition that is applied to seed and/or the amount of other additives select in the so a kind of mode of plant that can not adversely affect the germination of seed or can not damage generation.The special situation may under some rate of application with the active compound of phytotoxic effect, this point must keep in mind.

When resisting sanitary insect pest and grain storage pest, active compound of the present invention has good stability and in timber and soil, also shows good residual activity the alkali on calcium carbonate material.

Normally, when for the treatment of animal, active compound of the present invention can directly be used.Preferably they are used as the pharmaceutical composition that can contain some pharmaceutically acceptable vehicle known in the art and/or auxiliary agent.

In veterinary applications and animal rearing, active compound is used (=administration) by following form of medication in a known way: carry out administration in intestines with for example tablet, capsule, potus, drencs, granule, paste, pill, the form of feeding (feed-through) method, suppository; By for example injection (intramuscular, subcutaneous, intravenously, intraperitoneal etc.), implant and carry out administered parenterally; Pass through nasal administration; For example to take a shower (bathing) or to flood, spray, pour into a mould the form of (pouring on) and drop, cleaning, dusting, and carry out percutaneous drug delivery by means of moldings such as neck ring, ear tag, tail tag, limbs ligature (limb band), halter, concentrator marker etc. containing active compound.Described active compound can be mixed with shampoo or the suitable preparation that can use in as pump sprays and atomizer spray agent in aerosol, non-pressurised sprays.

When for domestic animal, poultry, domestic animal etc., the preparation (for example pulvis, wettable powder [" WP "], emulsion, missible oil [" EC "], can flowing agent, homogeneous phase solution and suspension [" SC "]) that active compound of the present invention can be used as the active compound that contains 1-80 % by weight amount directly use or dilution (for example diluting 000 times of 100-10) after use, or can be used as chemical bath agent and use.

In the time using in veterinary applications, active compound of the present invention can combine and use with suitable synergistic agent or other active compounds for example miticide, sterilant, wormer, protozoacide medicament.

To more specifically illustrate the present invention by embodiment.But the present invention should not only limit to these embodiment.

synthetic example 1

N-{4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] benzyl } ethanamide (numbering 1-1)

synthetic example 1-1

Synthesizing of 4-tolyl aldehyde oxime

The solution of the second alcohol and water of 4-tolyl aldehyde (5g), hydroxy amine hydrochloric acid salt (4.34g) and sodium acetate (6.23g) is at room temperature stirred 1 hour.Reaction soln is with after t-butyl methyl ether dilution, by this solution with water and saturated brine washing.Organic layer anhydrous magnesium sulfate drying.Remove solvent under reduced pressure, obtain 4-tolyl aldehyde oxime (5g).

1H-NMR(CDCl3)δ：2.37(3H，s)，7.19(2H，d)，7.46(2H，d)，8.12(1H，s)

synthetic example 1-2

[5-(3,5-dichlorophenyl)-3-(4-aminomethyl phenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole synthetic

Dimethyl formamide (20mL) solution of 4-tolyl aldehyde oxime (2g) and N-chlorosuccinimide (2.17g) is stirred 1 hour at 55 DEG C.Reaction soln is with after t-butyl methyl ether dilution, by this solution with water and saturated brine washing.Organic layer anhydrous magnesium sulfate drying.Remove solvent under reduced pressure, obtain N-hydroxy-4-methyl benzene carboxylic imino-chlorine (2g).By gained N-hydroxy-4-methyl benzene carboxylic imino-chlorine and the chloro-5-[1-of 1,3-bis-(trifluoromethyl) vinyl] toluene (50mL) vlil of benzene (5.3g) 8 hours.Remove solvent under reduced pressure, residuum, by silica gel chromatography purifying, obtains [5-(3,5-dichlorophenyl) 3-(4-aminomethyl phenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole (5.0g).

1H-NMR(CDCl3)δ：2.37(3H，s)，3.87(2H，dd)，7.22-7.25(3H，m)，7.51-7.56(4H，m)。

synthetic example 1-3

3-[4-(brooethyl) phenyl]-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole synthetic

By 5-(3,5-dichlorophenyl)-3-(4-aminomethyl phenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole (5.3g), N-bromosuccinimide (3.7g) and 2, ethylene dichloride (40mL) vlil of 2 '-Diisopropyl azodicarboxylate (0.1g) 3 hours.Remove under reduced pressure after solvent, residuum dilutes by t-butyl methyl ether, and by this solution with water and saturated brine washing.Organic layer anhydrous magnesium sulfate drying.Remove solvent under reduced pressure, then residuum passed through to silica gel chromatography purifying, obtain 3-[4-(brooethyl) phenyl]-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole (2.5g).

1H-NMR(CDCl3)δ：3.66-4.10(2H，m)，4.49(2H，s)，7.26-7.69(7H，m)。

synthetic example 1-4

2-{4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] benzyl }-1H-isoindole-1,3 (2H)-diketone synthetic

By 3-[4-(brooethyl) phenyl]-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4, DMF (20mL) solution of 5-dihydro-isoxazole (1-5g) and potassium phthalimide (0-61g) at room temperature stirs 8 hours.Reaction soln is with after t-butyl methyl ether dilution, by this solution with water and saturated brine washing.Use anhydrous magnesium sulfate drying organic layer.Remove solvent under reduced pressure, then, by silica gel chromatography purifying residuum, obtain 3-[4-(brooethyl) phenyl]-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole (0.8g).

1H-NMR(CDCl3)δ：3.85(2H，dd)，4.87(2H，s)，7.40-7.89(13H，m)。

synthetic example 1-5

1-{4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] phenyl } methylamine synthetic

By 2-{4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] benzyl }-1H-isoindole-1, methyl alcohol (5mL) solution of 3 (2H)-diketone (0.65g) and the hydrazine aqueous solution (0.07g) refluxes 1 hour.Reaction soln is with after t-butyl methyl ether dilution, by this solution with water and saturated brine washing.Organic layer anhydrous magnesium sulfate drying.Remove solvent under reduced pressure, then residuum passed through to silica gel chromatography purifying, obtain 1-{4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] phenyl } methylamine (0.2g).

1H-NMR(CDCl3)δ：3.89(2H，dd)，4.47(2H，s)，7.39-7.40(3H，m)，7.52-7.52(2H，m)，7.61-7.63(2H，m)。

synthetic example 1-6

N-{4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] benzyl } ethanamide synthetic

To 1-{4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] phenyl } in tetrahydrofuran (THF) (5mL) solution of methylamine (0.2g) and triethylamine (0.08g), dropwise add Acetyl Chloride 98Min. (0.05g), and this mixture is at room temperature stirred 1 hour.Reaction soln is with after t-butyl methyl ether dilution, by this solution with water and saturated brine washing.Organic layer anhydrous magnesium sulfate drying.Remove solvent under reduced pressure, then residuum passed through to silica gel chromatography purifying, obtain N-{4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] benzyl } ethanamide (0.05g).

1H-NMR(CDCl3)δ：2.04(3H，s)，3.88(2H，dd)，4.45(2H，d)，6.06(1H，s)，7.32(2H，d)，7.42-7.42(1H，m)，7.49-7.52(2H，m)，7.59-7.62(2H，m)。

synthetic example 2

synthetic example 2-1

N-{4-[(oxyimino) methyl] benzyl } ethanamide synthetic

N-(4-formyl radical benzyl) ethanamide (1.7g), hydroxy amine hydrochloric acid salt (1.0g) and the ethanol (10mL) of sodium acetate (1.0g) and the solution of water (6mL) are at room temperature stirred 1 hour.Reaction soln is with after t-butyl methyl ether dilution, by this solution with water and saturated brine washing.Organic layer anhydrous magnesium sulfate drying.Remove solvent under reduced pressure, obtain crude product N-{4-[(oxyimino) methyl]-benzyl } ethanamide (1.8g).

synthetic example 2-2

By N-{4-[(oxyimino) methyl] benzyl } ethanamide (0.5g) is dissolved in N, in dinethylformamide (20mL), in this solution, add N-chlorosuccinimide (0.38g), and this mixture is at room temperature stirred 2 hours.In this reaction soln, add 1, the chloro-5-[1-of 3-bis-(trifluoromethyl) vinyl] benzene (0.75g), and this mixture is cooled to after 0 DEG C, to the N that dropwise adds triethylamine (0.58g) in this mixture, dinethylformamide (2mL) solution, then at room temperature stirs this mixture 8 hours.After adding water and being extracted with ethyl acetate, organic layer is washed and is used anhydrous magnesium sulfate drying with saturated brine.Remove solvent under reduced pressure, then residuum passed through to silica gel chromatography purifying, obtain N-{4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] benzyl } ethanamide (0.3g).

synthetic example 3

The bromo-4-[5-of N-{2-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] benzyl }-N-(pyridine-2-ylmethyl) ethanamide (numbering 1-15)

synthetic example 3-1

The bromo-4-of 3-[3-(brooethyl) phenyl]-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole synthetic

By 3-(the bromo-4-aminomethyl phenyl of 3-)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole (1.2g), N-bromosuccinimide (0.54g) and 2, ethylene dichloride (20mL) vlil of 2 '-Diisopropyl azodicarboxylate (0.05g) 3 hours.Remove solvent under reduced pressure, residuum dilutes by t-butyl methyl ether, and by this solution with water and saturated brine washing.Organic layer anhydrous magnesium sulfate drying.Remove solvent under reduced pressure, and residuum passed through to silica gel chromatography purifying, obtain the bromo-4-of 3-[3-(brooethyl) phenyl]-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole (1.0g).

1H-NMR(CDCl3)δ：3.86(2H，dd)，4.59(2H，s)，7.46-7.6 1(5H，m)，7.85-7.86(1H，m)。

synthetic example 3-2

The bromo-4-[5-of 1-{2-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] phenyl }-N-(pyridine-2-ylmethyl) methylamine synthetic

By bromo-3-[3-4-(brooethyl) phenyl]-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4, acetonitrile (20mL) vlil of 5-dihydro-isoxazole (1.8g), 2-aminomethyl pyridine (0.38g) and salt of wormwood (0.97g) 3 hours.Reaction soln is with after t-butyl methyl ether dilution, by this solution with water and saturated brine washing.Organic layer anhydrous magnesium sulfate drying.Remove solvent under reduced pressure, and residuum is passed through to silica gel chromatography purifying, obtain the bromo-4-[5-of 1-{2-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] phenyl }-N-(pyridine-2-ylmethyl) methylamine (1.0g).

1H-NMR(CDCl3)δ：3.67(1H，d)，3.95-3.96(4H，m)，4.03-4.09(1H，m)，7.17-7.19(1H，m)，7.31-7.34(1H，m)，7.43-7.43(1H，m)，7.49-7.52(2H，m)，7.57-7.58(2H，m)，7.62-7.69(1H，m)，7.82-7.85(1H，m)，8.56-8.58(1H，m)。

synthetic example 3-3

The bromo-4-[5-of N-{2-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] benzyl }-N-(pyrodin-2-ylmethyl) ethanamide synthetic

To the bromo-4-[5-(3 of 1-{2-, 5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] phenyl } in tetrahydrofuran (THF) (5mL) solution of-N-(pyridine-2-ylmethyl) methylamine (0.22g) and triethylamine (0.06g), dropwise add Acetyl Chloride 98Min. (0.04g), and this mixture is at room temperature stirred 1 hour.Reaction soln is with after t-butyl methyl ether dilution, by this solution with water and saturated brine washing.Organic layer anhydrous magnesium sulfate drying.Remove solvent under reduced pressure, then residuum is passed through to silica gel chromatography purifying, obtain the bromo-4-[5-(3 of N-{2-, 5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] benzyl }-N-(pyrodin-2-ylmethyl) ethanamide (0.15g).

1H-NMR(CDCl3)δ：2.10-2.22(3H，m)，3.63-4.13(2H，m)，4.63-4.74(4H，m)，7.14-7.90(9H，m)，8.51-8.59(1H，m)。

synthetic example 4

N-{4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl]-2-nitrobenzyl } ethanamide (1-60) synthetic

synthetic example 4-1

Synthesizing of 4-methyl-3-nitro phenyl aldehyde

Adding under ice-cooled condition, dioxane (30mL) solution of 4-methyl-3-nitro Benzoyl chloride (5.5g) is dropwise being added in the solution of water (30mL), dioxane (30mL) and sodium borohydride (2.5g).This reaction soln is refluxed 1 hour, and after cooling, this solution is passed through to diatomite filtration.In filtrate, add water, mixture is extracted with ethyl acetate, and organic layer anhydrous magnesium sulfate drying.Remove solvent under reduced pressure, obtain the crude product (4g) of (4-methyl-3-nitro phenyl) methyl alcohol.

This crude product is dissolved in to methylene dichloride (200mL), in this solution, adds Manganse Dioxide (20g), and this mixture is at room temperature stirred 10 hours.After this reaction mixture suction filtration, remove solvent under reduced pressure, then residuum is passed through to silica gel chromatography purifying, obtain 4-methyl-3-nitro phenyl aldehyde (3.5g).

1H-NMR(CDCl3)δ：2.70(3H，s)，7.55(1H，d)，8.03(1H，dd)，8.46(1H，d)，10.04(1H，s)。

synthetic example 4-2

5-(3,5-dichlorophenyl)-3-(4-methyl-3-nitro phenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole synthetic

Adding under ice-cooled condition, tetrahydrofuran (THF) (50mL) solution of 4-methyl-3-nitro phenyl aldehyde (3.5g) is dropwise added in the tetrahydrofuran (THF) (50mL) of hydroxy amine hydrochloric acid salt (3.0g) and sodium acetate (4.0g) and the solution of water (50mL), and after dropwise having added, this mixture is at room temperature stirred 1 hour.Then this reaction soln dilute with water is extracted with ethyl acetate, and by organic layer anhydrous magnesium sulfate drying.Remove solvent under reduced pressure, obtain the crude product (3.5g) of 4-methyl-3-nitro benzaldoxime.

This crude product is dissolved in DMF (30mL), and adds N-chlorosuccinimide (1.4g) in this solution, and this mixture is stirred 1 hour at 55 DEG C.After stirring completes, adding under ice-cooled condition, in this mixture, adding the chloro-5-[1-of 1,3-bis-(trifluoromethyl) vinyl] benzene (2.5g), triethylamine (1.2g), and this mixture is at room temperature stirred 10 hours.Then reaction soln dilute with water is extracted with ethyl acetate, and by organic layer anhydrous magnesium sulfate drying.Remove solvent under reduced pressure, then residuum is passed through to silica gel chromatography purifying, obtain 5-(3,5-dichlorophenyl)-3-(4-methyl-3-nitro phenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole (2.1g).

1H-NMR(CDCl3)δ：2.63(3H，s)，3.72(1H，d)，4.10(1H，d)，7.43-7.51(4H，m)，7.88-7.91(1H，m)，8.15-8.16(1H，m)。

synthetic example 4-3

3-[4-(brooethyl)-3-nitrophenyl]-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole synthetic

By 5-(3,5-dichlorophenyl)-3-(4-methyl-3-nitro phenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole (1.9g), N-bromosuccinimide (0.9g) and 2, the dichloroethane solution reflux of 2 '-Diisopropyl azodicarboxylate (0.1g) 3 hours.Reaction soln washes with water, and by organic layer anhydrous magnesium sulfate drying.Remove solvent under reduced pressure, then residuum is passed through to silica gel chromatography purifying, obtain 3-[4-(brooethyl)-3-nitrophenyl]-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole (1.2g).

1H-NMR(CDCl3)δ：3.73(1H，d)，4.11(1H，d)，4.84(2H，s)，7.44-7.68(4H，m)，7.97-8.00(1H，m)，8.24-8.24(1H，m)。

synthetic example 4-4

1-{4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl]-2-nitrophenyl } methylamine synthetic

Adding under ice-cooled condition, by 3-[4-(brooethyl)-3-nitrophenyl]-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4, tetrahydrofuran (THF) (10mL) solution of 5-dihydro-isoxazole (1.0g) dropwise adds 28% the ammonia (aqueous solution, 5mL) and in the tetrahydrofuran (THF) (10mL) of tetrabutylammonium iodide (0.05g) and the solution of methyl alcohol (20mL), then this mixture is at room temperature stirred 10 hours.Reaction soln dilute with water, is then extracted with ethyl acetate, and by organic layer anhydrous magnesium sulfate drying.Remove solvent under reduced pressure, then residuum passed through to silica gel chromatography purifying, obtain 1-{4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl]-2-nitrophenyl } methylamine (0.8g).

1H-NMR(CDCl3)δ：3.74(1H，d)，3.94-4.18(3H，m)，7.43-7.52(3H，m)，7.77-7.79(1H，m)，7.97-8.00(1H，m)，8.20-8.24(1H，m)。

synthetic example 4-5

Adding under ice-cooled condition, to 1-{4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl]-2-nitrophenyl } in methylene dichloride (50mL) solution of methylamine (0.3g) and diacetyl oxide (0.1g), methylene dichloride (5mL) solution that dropwise adds triethylamine (0.1g), then at room temperature stirs this mixture 1 hour.This reaction soln dilute with water, then by organic layer anhydrous magnesium sulfate drying.Remove solvent under reduced pressure, then residuum passed through to silica gel chromatography purifying, obtain N-{4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl]-2-nitrobenzyl } ethanamide (0.2g).

1H-NMR(CDCl3)δ：2.04(3H，s)，3.72(1H，d)，4.11(1H，d)，4.69(2H，d)，6.27-6.29(1H，m)，7.45-7.49(3H，m)，7.80-7.91(2H，m)，8.29(1H，d)

synthetic example 5

N-{4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl]-2-methyl-benzyl } ethanamide (numbering 1-63)

synthetic example 5-1

Synthesizing of 4-formyl radical-2-methyl-toluate

At-70 DEG C, in tetrahydrofuran (THF) (100mL) solution of the bromo-2-tolyl acid of 4-(10g), add hexane (60mL) solution of 1.6M n-Butyl Lithium.This reaction mixture is stirred at-40 DEG C after 1 hour, at-70 DEG C to tetrahydrofuran (THF) (10mL) solution that adds DMF (10mL) in this mixture.After this mixture being stirred at-70 DEG C 1 hour and being then warmed to room temperature, this mixture is poured in ice and dilute with water.Water layer washs with hexane and uses concentrated hydrochloric acid acidifying, and throw out is extracted with ethyl acetate.Organic layer anhydrous magnesium sulfate drying.Remove solvent under reduced pressure, obtain the crude product (5g) of 4-formyl radical-2-tolyl acid.

This crude product is dissolved in methylene dichloride (50mL) and methyl alcohol (15.0g), and by 1-ethyl-3-(3-dimethylamino-propyl group) carbodiimide hydrochloride (12.0g), N, N-dimethyl aminopyridine (8.0g) adds in this solution, and this mixture is at room temperature stirred 10 hours.2N salt acid elution for reaction mixture, and by organic layer anhydrous magnesium sulfate drying.Remove solvent under reduced pressure, then residuum is passed through to silica gel chromatography purifying, obtain 4-formyl radical-2-methyl-toluate (1.3g).

1H-NMR(CDCl3)δ：2.64(3H，s)，3.90(3H，s)，7.73-7.76(2H，m)，7.98-8.02(1H，m)，10.07(1H，s)。

synthetic example 5-2

4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl]-2-methyl-toluate synthetic

Adding under ice-cooled condition; tetrahydrofuran (THF) (50mL) solution of 4-formyl radical-2-methyl-toluate (1.3g) is dropwise added in the solution of hydroxy amine hydrochloric acid salt (1.0g) in tetrahydrofuran (THF) (50mL) and water (50mL), sodium acetate (1.2g); and after dropwise having added, this mixture is at room temperature stirred 1 hour.Then reaction mixture dilute with water is extracted with ethyl acetate, and by organic layer anhydrous magnesium sulfate drying.Remove solvent under reduced pressure, obtain 4-[(oxyimino) methyl] crude product (1.3g) of-2-methyl-toluate.

This crude product is dissolved in to DMF (30mL), then in this solution, adds N-chlorosuccinimide (1.0g), and this mixture is stirred 1 hour at 55 DEG C.After stirring completes, adding under ice-cooled condition, in this mixture, add the chloro-5-[1-of 1,3-bis-(trifluoromethyl) vinyl] benzene (1.7g) and triethylamine (0.8g), then at room temperature stir this mixture 10 hours.Then reaction mixture dilute with water is extracted with ethyl acetate, and by organic layer anhydrous magnesium sulfate drying.Remove solvent under reduced pressure, then residuum passed through to silica gel chromatography purifying, obtain 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl]-2-methyl-toluate (1.9g).

1H-NMR(CDCl3)δ：2.63(3H，s)，3.68(1H，d)，3.91(3H，s)，4.11(2H，d)，7.42-7.54(5H，m)，7.95-7.96(1H，m)。

synthetic example 5-3

1-{4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl]-2-aminomethyl phenyl } methylamine synthetic

Adding under ice-cooled condition, by 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] tetrahydrofuran (THF) (30mL) solution of-2-methyl-toluate (1.0g) dropwise adds in tetrahydrofuran (THF) (50mL) solution of lithium aluminum hydride (0.1g), and after having added, this mixture is at room temperature stirred 1 hour.Reaction soln is fallen on ice, then add 2N hydrochloric acid (30mL) in batches.This mixture is extracted with ethyl acetate, and by organic layer anhydrous magnesium sulfate drying.Remove solvent under reduced pressure, obtain the crude product (0.9g) of { 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl]-2-aminomethyl phenyl } methyl alcohol.

This crude product is dissolved in to methylene dichloride (50mL), and adds triethylamine (0.3g) in this solution.Then adding under ice-cooled condition, dropwise adding methylene dichloride (10mL) solution of methylsulfonyl chloride (0.3g), and this mixture is at room temperature stirred 1 hour.This reaction mixture is washed with water, and use anhydrous magnesium sulfate drying organic layer.Remove solvent under reduced pressure, then by silica gel chromatography purifying residuum, obtain 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] crude product (1.0g) of-2-methyl-benzyl mesylate.

Adding under ice-cooled condition, the tetrahydrofuran (THF) of this crude product (10mL) solution is dropwise added in the tetrahydrofuran (THF) (10mL) of 28% ammonia (5mL) and tetrabutylammonium iodide (0.05g) and the aqueous solution of methyl alcohol (20mL), and this mixture is at room temperature stirred 10 hours.Reaction mixture dilute with water, is then extracted with ethyl acetate, and by organic layer anhydrous magnesium sulfate drying.Remove solvent under reduced pressure, then residuum passed through to silica gel chromatography purifying, obtain 1-{4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl]-2-aminomethyl phenyl } methylamine (0.4g).

1H-NMR(CDCl3)δ：2.39(3H，d)，3.69(1H，d)，3.89(2H，s)，4.11(1H，d)，7.42-7.49(6H，m)。

synthetic example 5-4

N-{4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl]-2-methyl-benzyl } ethanamide synthetic

Adding under ice-cooled condition, to 1-{4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl]-2-aminomethyl phenyl } in methylene dichloride (50mL) solution of methylamine (0.2g) and diacetyl oxide (0.1g), methylene dichloride (5mL) solution that dropwise adds triethylamine (0.1g), then at room temperature stirs this mixture 1 hour.This reaction mixture is washed with water, and by organic layer anhydrous magnesium sulfate drying.Remove solvent under reduced pressure, then residuum passed through to silica gel chromatography purifying, obtain N-{4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl]-2-methyl-benzyl } ethanamide (0.2g).

1H-NMR(CDCl3)δ：2.04(3H，s)，3.68(1H，d)，4.07(1H，d)，4.45(2H，d)，5.61-5.64(1H，m)，7.19-7.27(3H，m)，7.43-7.50(3H，m)

synthetic example 6

N-(cyano group 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] and phenyl } methyl)-N-(pyridine-2-ylmethyl)-ethanamide (numbering 1-11)

synthetic example 6-1

4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] phenyl aldehyde

To { 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] phenyl } in methylene dichloride (30mL) solution of methyl alcohol (1g), add activity oxidation manganese (1.8g), then this mixture is heated and at 40 DEG C, stirred 3 hours.Reaction mixture is by after diatomite filtration, and concentrating under reduced pressure gained filtrate, obtains 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] phenyl aldehyde (0.8g).

1H-NMR(CDCl3)δ：3.79-4.07(2H，m)，7.43-7.44(1H，m)，7.51-7.52(2H，m)，7.83-7.85(2H，m)，7.94-7.96(2H，m)，10.06(1H，s)

synthetic example 6-2

{ 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] phenyl } [(pyridine-2-ylmethyl) amino] acetonitrile synthetic

To 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] in tetrahydrofuran (THF) (5mL) solution of phenyl aldehyde (0.30g), 2-aminomethyl pyridine (0.09g) and trimethylsilyl cyanide (0.08g), add lithium perchlorate (0.8g), then this mixture is at room temperature stirred 1 hour.This reaction mixture, with after t-butyl methyl ether dilution, is washed this solution with water and saturated brine.Organic layer anhydrous magnesium sulfate drying.Remove solvent under reduced pressure, then residuum is passed through to silica gel chromatography purifying, obtain 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] phenyl [(pyridine-2-ylmethyl) amino] acetonitrile (0.15g).

1H-NMR(CDCl3)δ：3.65-3.83(5H，m)，7.05-7.57(11H，m)

synthetic example 6-3

N-(cyano group 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] and phenyl } methyl)-N-(pyridine-2-ylmethyl) ethanamide

To { 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] phenyl } [(pyridine-2-yl) methyl] amino] in tetrahydrofuran (THF) (5mL) solution of acetonitrile (0.05g) and triethylamine (0.05g), dropwise add Acetyl Chloride 98Min. (0.03g), and this mixture is at room temperature stirred 1 hour.This reaction mixture, with after t-butyl methyl ether dilution, is washed this solution with water and saturated brine.Organic layer anhydrous magnesium sulfate drying.Remove solvent under reduced pressure, then by silica gel chromatography purifying residuum, obtain N-(cyano group { 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] phenyl } methyl)-N-(pyridine-2-ylmethyl] ethanamide (0.10g).

1H-NMR(CDCl3)δ：2.28(3H，s)，3.86(2H，dd)，4.54-4.64(2H，m)，6.99-7.01(1H，m)，7.13-7.16(2H，m)，7.43-7.61(8H，m)，8.48-8.50(1H，m)

synthetic example 7

The bromo-4-[5-of N-{2-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] benzyl } second sulphamide (1-44) synthetic

By bromo-3-[3-4-(brooethyl) phenyl]-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole (0.3g) mixes with thioacetamide (0.04g), then this mixture is stirred 1 hour at 80 DEG C.Residuum, by silica gel chromatography purifying, obtains the bromo-4-[5-of N-{2-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] benzyl } second sulphamide (0.09g).

1H-NMR(CDCl3)δ：2.60(3H，s)，3.66-4.09(2H，m)，4.97(2H，d)，7.43-7.60(6H，m)，7.87(1H，d)

synthetic example 8

The bromo-4-[5-of 1-{2-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] benzyl }-4-methyl isophthalic acid, 4-dihydro-5H-tetrazolium-5-ketone (numbering 1-55) synthesizes

By bromo-3-[3-4-(brooethyl) phenyl]-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole (0.3g), 1-methyl isophthalic acid, DMF (10mL) solution of 4-dihydro-5H-tetrazolium-5-ketone (0.06g) and salt of wormwood (0.16g) at room temperature stirs 3 hours.This reaction mixture, with after t-butyl methyl ether dilution, is washed this solution with water and saturated brine.Organic layer anhydrous magnesium sulfate drying.Remove solvent under reduced pressure, then residuum is passed through to silica gel chromatography purifying, obtain the bromo-4-[5-of 1-{2-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] benzyl }-4-methyl isophthalic acid, 4-dihydro-5H-tetrazolium-5-ketone (0.1g).

1H-NMR(CDCl3)δ：3.65-4.08(5H，m)，5.24(2H，s)，7.28-7.30(1H，m)，7.42-7.43(1H，m)，7.49-7.50(2H，m)，7.60-7.62(1H，m)，7.89-7.89(1H，m)。

synthetic example 9

N-{2-cyano group-4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] benzyl }-N-(pyridine-2-ylmethyl) ethanamide (1-61) synthetic

Under argon gas atmosphere, to the bromo-4-[5-(3 of N-{2-, 5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] benzyl } in dimethyl formamide (20mL) solution of-N-(pyrodin-2-ylmethyl) ethanamide (0.75g), add zinc cyanide (0.11g) and tetrakis triphenylphosphine palladium (0.29g), then this mixture is stirred 4 hours at 80 DEG C.This reaction mixture, with after t-butyl methyl ether dilution, is washed this solution with water and saturated brine.Organic layer anhydrous magnesium sulfate drying.Remove solvent under reduced pressure, then residuum is passed through to silica gel chromatography purifying, obtain N-{2-cyano group-4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl] benzyl }-N-(pyridine-2-ylmethyl) ethanamide (0.6g).

1H-NMR(CDCl3)δ：2.27-2.31(3H，m)，3.75-4.06(2H，m)，4.68-4.87(4H，m)，7.17-7.96(9H，m)，8.49-8.57(1H，m)。

synthetic example 10

3-(4-aminomethyl phenyl)-5-(trifluoromethyl)-5-[3-(trifluoromethyl) phenyl]-4,5-dihydro-isoxazole synthetic

synthetic example 10-1

4,4,4-tri-fluoro-3-hydroxyl-1-(4-aminomethyl phenyl)-3-[3-(trifluoromethyl) phenyl] fourth-1-ketone

By 2, the fluoro-1-[3-of 2,2-tri-(trifluoromethyl) phenyl] tetrahydrofuran (THF) (30mL) solution of ethyl ketone (3.0g), 4-methyl acetophenone (1.1g) and lithium hydride (0.13g) stirs 3 hours at 60 DEG C.This reaction soln is with after t-butyl methyl ether dilution, by this solution with water and saturated brine washing.Organic layer anhydrous magnesium sulfate drying.Remove solvent under reduced pressure, then residuum passed through to silica gel chromatography purifying, obtain 4,4,4-tri-fluoro-3-hydroxyl-1-(4-aminomethyl phenyl)-3-[3-(trifluoromethyl) phenyl] fourth-1-ketone (3.0g).

1H-NMR(CDCl3)δ：2.44(3H，s)，3.67-3.94(2H，m)，5.96(1H，s)，7.39-7.78(8H，m)。

synthetic example 10-2

4,4,4-tri-fluoro-3-hydroxyl-1-(4-aminomethyl phenyl)-3-[3-(trifluoromethyl) phenyl] fourth-1-ketoxime

By 4,4,4-tri-fluoro-3-hydroxyl-1-(4-aminomethyl phenyl)-3-[3-(trifluoromethyl) phenyl] ethanol (10mL) vlil 5 hours of fourth-1-ketone (1.0g), hydroxy amine hydrochloric acid salt (0.28g) and pyridine (0.42g).Reaction soln is with after t-butyl methyl ether dilution, by this solution with water and saturated brine washing.Organic layer anhydrous magnesium sulfate drying.Remove solvent under reduced pressure, obtain 4,4,4-tri-fluoro-3-hydroxyl-1-(4-aminomethyl phenyl)-3-[3-(trifluoromethyl) phenyl] fourth-1-ketoxime (1.0g).

1H-NMR(CDCl3)δ：2.30(3H，s)，3.39(1H，t，J＝6.8Hz)，4.02(1H，d，J＝13.6Hz)，5.25(1H，s)，6.94-7.69(8H，m)。

synthetic example 10-3

3-(4-aminomethyl phenyl)-5-(trifluoromethyl)-5-[3-(trifluoromethyl) phenyl]-4,5-dihydro-isoxazole

To 4,4,4-tri-fluoro-3-hydroxyl-1-(4-aminomethyl phenyl)-3-[3-(trifluoromethyl) phenyl] in tetrahydrofuran (THF) (10mL) solution of fourth-1-ketoxime (0.45g) and triphenyl phosphine (0.60g), add diethylazodicarboxylate (diethyl azodicarboxilate) (0.44g), and this mixture is at room temperature stirred 24 hours.Reaction soln is with after t-butyl methyl ether dilution, by this solution with water and saturated brine washing, then by organic layer anhydrous magnesium sulfate drying.Remove solvent under reduced pressure, obtain 3-(4-aminomethyl phenyl)-5-(trifluoromethyl)-5-[3-(trifluoromethyl) phenyl]-4,5-dihydro-isoxazole (0.11g).

1H-NMR(CDCl3)δ：2.38(3H，s)，3.73(1H，d)，4.13(1H，d)，7.22-7.25(2H，m)，7.61-7.82(6H，m)

synthetic example 11

Synthesizing of 4-(the fluoro-3-hydroxyl-3-of 4,4,4-tri-phenyl butyryl radicals) methyl benzoate

Hexane (30mL) solution of fluoro-2,2,2-tri-1-Phenyl ethyl ketone (2.0g), 4-acetylbenzoic acid methyl esters (1.02g) and lithium hydride (0.13g) is stirred 3 hours at 40 DEG C.This reaction soln is with after t-butyl methyl ether dilution, by this solution with water and saturated brine washing.Organic layer anhydrous magnesium sulfate drying.Remove solvent under reduced pressure, then residuum is passed through to silica gel chromatography purifying, obtain 4-(the fluoro-3-hydroxyl-3-of 4,4,4-tri-phenyl butyryl radicals) methyl benzoate (1.2g).

1H-NMR(CDCl3)δ：3.68(1H，d)，3.96(3H，s)，4.06(1H，d)，5.43(1H，s)，7.34-7.37(4H，m)，7.58-7.61(3H，m)，7.96-8.16(2H，m)

synthetic example 12

N-[(4-{5-[3, the chloro-5-of 4-bis-(trifluoromethyl) phenyl]-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl } naphthalene-1-yl) methyl] ethanamide (7-128) synthetic

N-chlorosuccinimide (0.06g) is added to N-({ 4-[(oxyimino) methyl] naphthalene-1-yl } methyl) N of ethanamide (0.1g), in dinethylformamide (10ml) solution, and this reaction mixture is at room temperature stirred 2 hours.In this reaction mixture, add the chloro-3-of 1,2-bis-(trifluoromethyl)-5-[1-(trifluoromethyl) vinyl] benzene (0.75g) and saleratus (0.13g), and this mixture is at room temperature stirred 8 hours.Water is poured in this reaction mixture, and be extracted with ethyl acetate.Organic layer salt water washing, and use anhydrous magnesium sulfate drying.Remove solvent under reduced pressure, and residuum is purified with silica gel column chromatography, obtain N-[(4-{5-[3, the chloro-5-of 4-bis-(trifluoromethyl) phenyl]-5-(trifluoromethyl)-4,5-dihydro-isoxazole-3-yl } naphthalene-1-yl) methyl] ethanamide (0.1g).

1H-NMR(CDCl3)δ：2.15(3H，s)，3.89(1H，d)，4.30(1H，d)，4.88(2H，d)，5.97-6.00(1H，m)，7.42-7.44(2H，m)，7.61-7.66(2H，m)，7.87-7.91(1H，m)，8.01-8.05(2H，m)，8.84-8.88(1H，m)

Be shown in together with its physical values in table 1-9 with formula of the present invention (I) compound obtaining according to described in detail above method and intermediate thereof by being similar to the method for above-mentioned synthetic example.The compound obtaining in synthetic example mentioned above is also shown in following table.

Table 1

Numbering

(X)l

R

Y

R ¹

R ²

R ⁴

R ³

A

n

1-1

3,5-, bis-Cl

CF3

H

MeCO

H

CH

1

1-2

3,5-, bis-Cl

CF3

H

MeCO

CH

1

1-3

3,5-, bis-Cl

CF3

H

MeCO

2-pyridyl-CO

CH

1

1-4

3,5-, bis-Cl

CF3

H

HCO

2-pyridyl-CH2

CH

1

1-5

3,5-, bis-Cl

CF3

H

MeCO

2-pyridyl-CH2

CH

1

1-6

3,5-, bis-Cl

CF3

H

EtCO

2-pyridyl-CH2

CH

1

1-7

3,5-, bis-Cl

CF3

H

Me2NCO

2-pyridyl-CH2

CH

1

1-8

3,5-, bis-Cl

CF3

H

MeSO2

2-pyridyl-CH2

CH

1

1-9

3,5-, bis-Cl

CF3

H

2-pyridyl-CO

2-pyridyl-CH2

CH

1

1-10

3,5-, bis-Cl

CF3

H

CN

H

MeCO

H

CH

1

1-11

3,5-, bis-Cl

CF3

H

CN

H

MeCO

2-pyridyl-CH2

CH

1

1-12

3,5-, bis-Cl

CF3

Br

H

HCO

H

CH

1

1-13

3,5-, bis-Cl

CF3

Br

H

MeCO

H

CH

1

1-14

3,5-, bis-Cl

CF3

Br

H

MeCO

CH

1

1-15

3,5-, bis-Cl

CF3

Br

H

MeCO

2-pyridyl-CH2

CH

1

1-16

3,5-, bis-Cl

CF3

Br

H

MeCO

3-pyridyl CH2

CH

1

1-17

3,5-, bis-Cl

CF3

Br

H

MeCO

4-pyridyl-CH2

CH

1

1-18

3,5-, bis-Cl

CF3

Br

H

MeCO

Benzyl

CH

1

1-19

3,5-, bis-Cl

CF3

Br

H

EtCO

H

CH

1

1-20

3,5-, bis-Cl

CF3

Br

H

N-PrCO

H

CH

1

1-21

3,5-, bis-Cl

CF3

Br

H

Iso-PrCO

H

CH

1

1-22

3,5-, bis-Cl

CF3

Br

H

Uncle-BuCO

H

CH

1

1-23

3,5-, bis-Cl

CF3

Br

H

CF3CO

H

CH

1

1-24

3,5-, bis-Cl

CF3

Br

H

PhCO

H

CH

1

1-25

3,5-, bis-Cl

CF3

Br

H

2-pyridyl-CO

H

CH

1

Numbering

(X)l

R

Y

R ¹

R ²

R ⁴

R ³

A

n

1-109

3-CH3-S (O)

CF3

Br

H

MeCO

H

CH

1

1-110

3-CH3-S (O)2

CF3

Br

H

MeCO

H

CH

1

1-111

3-CF3S

CF3

Br

H

MeCO

H

CH

1

1-112

3-CF3-S( O)

CF3

Br

H

MeCO

H

CH

1

1-113

3-CF3-S( O)2

CF3

Br

H

MeCO

H

CH

1

1-114

3-OH

CF3

Br

H

MeCO

H

CH

1

1-115

3-SH

CF3

Br

H

MeCO

H

CH

1

1-116

3-NH2

CF3

Br

H

MeCO

H

CH

1

1-117

3-NH-C O-CH3

CF3

Br

H

MeCO

H

CH

1

1-118

3-NH-C O-CF3

CF3

Br

H

MeCO

H

CH

1

1-119

3-NH-C O2CH3

CF3

Br

H

MeCO

H

CH

1

1-120

3-NH-C O2-CH2- CCl3

CF3

Br

H

MeCO

H

CH

1

1-121

3-NH-S O2CH3

CF3

Br

H

MeCO

H

CH

1

1-122

3-NH-S O2CF3

CF3

Br

H

MeCO

H

CH

1

1-123

3,5-, bis-Cl

CF3

NHCOC F3

H

MeCO

H

CH

1

1-124

3,5-, bis-Cl

CF3

NH-SO2 CH3

H

MeCO

H

CH

1

1-125

3,5-, bis-Cl

CF3

NH-SO2 CF3

H

MeCO

H

CH

1

1-126

3,5-, bis-Cl

CF3

H

MeCO

H

CH

2

1-127

3,5-, bis-Br

CF3

H

MeCO

H

CH

1

1-128

3-F

CF3

Br

H

MeCO

H

CH

1

1-129

3,4,5-, tri-Cl

CF3

Br

H

MeCO

H

CH

1

1-130

3,5-, bis-Cl-4-Me

CF3

Br

H

MeCO

H

CH

1

1-131

3,4,5-, tri-F

CF3

Br

H

MeCO

H

CH

1

1-132

3,4,5-, tri-Br

CF3

Br

H

MeCO

H

CH

1

1-133

3,5-, bis-Cl, 4-Br

CF3

Br

H

MeCO

H

CH

1

1-134

3,5-, bis-Cl, 4-Br

CE3

Br

H

EtCO

H

CH

1

1-135

3,5-, bis-Br, 4-Cl

CF3

Br

H

MeCO

H

CH

1

1-136

3,5-, bis-Br, 4-Cl

CF3

Br

H

EtCO

H

CH

1

1-137

3,5-, bis-Cl, 4-NH2

CF3

Br

H

MeCO

H

CH

1

Numbering

(X)l

R

Y

R ¹

R ²

R ⁴

R ³

A

n

1-138

3,5-, bis-Br, 4-NH2

CF3

Br

H

MeCO

H

CH

1

1-139

3,5-, bis-Br, 4-NH2

CF3

Br

H

EtCO

H

CH

1

1-140

3,4-, bis-Cl, 5-CF3

CF3

Br

H

MeCO

H

CH

1

1-141

3,5-, bis-Cl, 4-CF3

CF3

Br

H

MeCO

H

CH

1

1-142

3,5-, bis-Cl, 4-CF3

CF3

Br

H

EtCO

H

CH

1

1-143

3-Cl， 5-CF3

CF3

Br

H

MeCO

H

CH

1

1-144

3-Cl， 4-CF3

CF3

Br

H

MeCO

H

CH

1

1-145

3-Br， 5-CF3

CF3

Br

H

MeCO

H

CH

1

1-146

3-Br， 4-CF3

CF3

Br

H

MeCO

H

CH

1

1-147

3-CF3， 4-F

CF3

Br

H

MeCO

H

CH

1

1-148

3-Cl， 5-SCF3

CF3

Br

H

MeCO

H

CH

1

Table 2

Numbering

(X)l

R

Y

R ¹

R ²

R ⁴

R ³

A

n

2-1

3,5-, bis-Cl

CF3

H

CH

1

2-2

3,5-, bis-Cl

CF3

CH3

H

CH

1

2-3

3,5-, bis-Cl

CF3

F

H

CH

1

2-4

3,5-, bis-Cl

CF3

Cl

H

CH

1

2-5

3,5-, bis-Cl

CF3

Br

H

CH

1

2-6

3,5-, bis-Cl

CF3

I

H

CH

1

2-7

3,5-, bis-Cl

CF3

NO2

H

CH

1

2-8

3,5-, bis-Cl

CF3

CN

H

CH

1

2-9

3,5-, bis-Cl

CF3

MeS

H

CH

1

2-10

3,5-, bis-Cl

CF3

MeSO

H

CH

1

2-11

3,5-, bis-Cl

CF3

MeSO2

H

CH

1

2-12

3,5-, bis-Cl

CF3

CF3S

H

CH

1

2-13

3,5-, bis-Cl

CF3

CF3-S(O)

H

CH

1

2-14

3,5-, bis-Cl

CF3

CF3-S(O)2

H

CH

1

Numbering

(X)l

R

Y

R ¹

R ²

R ⁴

R ³

A

n

2-72

3,5-, bis-Cl

CF3

Br

H

CH

2

2-73

3-NH2

CF3

Br

H

CH

1

2-74

3-NHCOCH3

CF3

Br

H

CH

1

2-75

3-NHCOCF3

CF3

Br

H

CH

1

2-76

3-NHCO2CH3

CF3

Br

H

CH

1

2-77

3-NHCO2CH2CCl3

CF3

Br

H

CH

1

2-78

3-NHSO2CH3

CF3

Br

H

CH

1

2-79

3-NHSO2CF3

CF3

Br

H

CH

1

2-80

3,5-, bis-Cl

CF3

NHCOCF3

H

CH

1

2-81

3,5-, bis-Cl

CF3

NHSO2CH3

H

CH

1

2-82

3,5-, bis-Cl

CF3

NHSO2CF3

H

CH

1

2-83

3,5-, bis-Br

CF3

Br

H

CH

1

Table 4

Table 5

Numbering

(X)l

R

Y

R ¹

R ²

A

n

4-1

35-bis-Cl

CF3

H

CH

1

4-2

3,5-, bis-Cl

CF3

Me

H

CH

1

4-3

35-bis-Cl

CF3

F

H

CH

1

4-4

3,5-, bis-Cl

CF3

Cl

H

CH

1

4-5

3,5-, bis-Cl

CF3

Br

H

CH

1

4-6

3,5-, bis-Cl

CF3

I

H

CH

1

4-7

3,5-, bis-Cl

CF3

NO2

H

CH

1

4-8

3,5-, bis-Cl

CF3

CN

H

CH

1

4-9

3,5-, bis-Cl

CF3

MeS

H

CH

1

4-10

3,5-, bis-Cl

CF3

MeSO

H

CH

1

4-11

3,5-, bis-Cl

CF3

MeSO2

H

CH

1

4-12

3,5-, bis-Cl

CF3

CF3S

H

CH

1

4-13

3,5-, bis-Cl

CF3

CF3S(O)

H

CH

1

4-14

3,5-, bis-Cl

CF3

CF3S(O)2

H

CH

1

4-15

3,5-, bis-Cl

CF3

OMe

H

CH

1

4-16

3,5-, bis-Cl

CF3

OCF3

H

CH

1

4-17

3,5-, bis-Cl

CF3

OH

H

CH

1

4-18

3,5-, bis-Cl

CF3

SH

H

CH

1

4-19

3,5-, bis-Cl

CF3

NH2

H

CH

1

4-20

3,5-, bis-Cl

CF3

NHCOMe

H

CH

1

4-21

3,5-, bis-Cl

CF3

NHCO2Me

H

CH

1

4-22

3,5-, bis-Cl

CF3

NHCO2CH2CCl3

H

CH

1

4-23

3,5-, bis-Br

CF3

Br

H

CH

1

4-24

3,4-, bis-Cl

CF3

Br

H

CH

1

4-25

3,4,5-, tri-Cl

CF3

Br

H

CH

1

4-26

3,5-, bis-Cl-4-Me

CF3

Br

H

CH

1

4-27

3-F

CF3

Br

H

CH

1

4-28

3-Cl

CF3

Br

H

CH

1

4-29

3-CF3

CF3

Br

H

CH

1

4-55

3-CF3

CF3

H

CH

1

4-30

4-CF3

CF3

Br

H

CH

1

4-31

3,5-, bis-CF3

CF3

Br

H

CH

1

4-32

3-NO2

CF3

Br

H

CH

1

4-33

3,5-, bis-Cl

CF3

Br

H

CH

1

4-34

3-CH3

CF3

Br

H

CH

1

4-35

3-CH3O

CF3

Br

H

CH

1

4-36

3-CN

CF3

Br

H

CH

1

4-37

3-CF3O

CF3

Br

H

CH

1

4-38

3-CH3S

CF3

Br

H

CH

1

4-39

3-CH3S(O)

CF3

Br

H

CH

1

4-40

3-CH3S(O)2

CF3

Br

H

CH

1

4-41

3-CF3S

CF3

Br

H

CH

1

4-42

3-CF3S(O)

CF3

Br

H

CH

1

4-43

3-CF3S(O)2

CF3

Br

H

CH

1

4-44

3-OH

CF3

Br

H

CH

1

4-45

3-SH

CF3

Br

H

CH

1

4-46

3-NH2

CF3

Br

H

CH

1

4-47

3-NHCOCH3

CF3

Br

H

CH

1

4-48

3-NHCOCF3

CF3

Br

H

CH

1

4-49

3-NHCO2CH3

CF3

Br

H

CH

1

4-50

3-NHCO2CH2CCl3

CF3

Br

H

CH

1

4-51

3-NHSO2CH3

CF3

Br

H

CH

1

4-52

3-NHSO2CF3

CF3

Br

H

CH

1

4-53

3,5-, bis-Cl

CF3

Br

Me

H

CH

1

4-54

3,5-, bis-Cl

CF3

Br

H

N

1

Table 6

Numbering	(X)l	R	Y	R ⁵	A
						5-1	H	CF3	H	Me	CH
5-2	3,5-, bis-Cl	CF3	H	Me	CH
						5-3	3,5-, bis-Cl	CF3	Me	Me	CH
5-4	3,5-, bis-Cl	CF3	F	Me	CH
						5-5	3,5-, bis-Cl	CF3	Cl	Me	CH
5-6	3,5-, bis-Cl	CF3	Br	Me	CH
						5-7	3,5-, bis-Cl	CF3	I	Me	CH
5-8	3,5-, bis-Cl	CF3	NO2	Me	CH
						5-9	3,5-, bis-Cl	CF3	CN	Me	CH
5-10	3,5-, bis-Cl	CF3	MeS	Me	CH
						5-11	3,5-, bis-Cl	CF3	MeSO	Me	CH
5-12	3,5-, bis-Cl	CF3	MeSO2	Me	CH
						5-13	3,5-, bis-Cl	CF3	CF3S	Me	CH
5-14	3,5-, bis-Cl	CF3	CF3S(O)	Me	CH
						5-15	3,5-, bis-Cl	CF3	CF3S(O)2	Me	CH
5-16	3,5-, bis-Cl	CF3	OMe	Me	CH
						5-17	3,5-, bis-Cl	CF3	OCF3	Me	CH
5-18	3,5-, bis-Cl	CF3	OH	Me	CH
						5-19	3,5-, bis-Cl	CF3	SH	Me	CH
5-20	3,5-, bis-Cl	CF3	NH2	Me	CH
						5-21	3,5-, bis-Cl	CF3	NHCOMe	Me	CH
5-22	3,5-, bis-Cl	CF3	NHCO2Me	Me	CH
						5-23	3,5-, bis-Cl	CF3	NHCO2CH2CCl3	Me	CH
5-24	3,5-, bis-Br	CF3	Br	Me	CH
						5-25	3,4-, bis-Cl	CF3	Br	Me	CH
5-26	3,4,5-, tri-Cl	CF3	Br	Me	CH
						5-27	3,5-, bis-Cl-4-Me	CF3	Br	Me	CH
5-28	3-F	CF3	Br	Me	CH
						5-29	3-Cl	CF3	Br	Me	CH
5-30	3-CF3	CF3	Br	Me	CH
						5-31	4-CF3	CF3	Br	Me	CH
5-32	3,5-, bis-CF3	CF3	Br	Me	CH
						5-33	3-NO2	CF3	Br	Me	CH
5-34	3,5-, bis-Cl	CF3	Br	Me	CH
						5-35	3-CH3	CF3	Br	Me	CH
5-36	3-CH3O	CF3	Br	Me	CH
						5-37	3-CN	CF3	Br	Me	CH
5-38	3-CF3O	CF3	Br	Me	CH
						5-39	3-CH3S	CF3	Br	Me	CH
5-40	3-CH3S(O)	CF3	Br	Me	CH
						5-41	3-CH3S(O)2	CF3	Br	Me	CH
5-42	3-CF3S	CF3	Br	Me	CH
						5-43	3-CF3S(O)	CF3	Br	Me	CH
5-44	3-CF3S(O)2	CF3	Br	Me	CH
						5-45	3-OH	CF3	Br	Me	CH
5-46	3-SH	CF3	Br	Me	CH
						5-47	3-NH2	CF3	Br	Me	CH

Numbering	(X)l	R	Y	R ⁵	A
						5-48	3-NHCOCH3	CF3	Br	Me	CH
5-49	3-NHCOCF3	CF3	Br	Me	CH
						5-50	3-NHCO2CH3	CF3	Br	Me	CH
5-51	3-NHCO2CH2CCl3	CF3	Br	Me	CH
						5-52	3-NHSO2CH3	CF3	Br	Me	CH
5-53	3-NHSO2CF3	CF3	Br	Me	CH
						5-54	3,5-, bis-Cl	CF3	Br	Me	N
5-55	3,5-, bis-Cl	CF3	Br	Et	CH
						5-56	3,5-, bis-Cl	CF3	Br	Uncle-Bu	CH

Table 7

Numbering

Y

R ¹

R ²

R ⁴

A

n

6-1

H

MeCO

CH

1

6-2

Me

H

MeCO

CH

1

6-3

F

H

MeCO

CH

1

6-4

Cl

H

MeCO

CH

1

6-5

Br

H

MeCO

CH

1

6-6

I

H

MeCO

CH

1

6-7

NO2

H

MeCO

CH

1

6-8

CN

H

MeCO

CH

1

6-9

MeS

H

MeCO

CH

1

6-10

MeSO

H

MeCO

CH

1

6-11

MeSO2

H

MeCO

CH

1

6-12

CF3S

H

MeCO

CH

1

6-13

CF3S(O)

H

MeCO

CH

1

6-14

CF3S(O)2

H

MeCO

CH

1

6-15

OCH3

H

MeCO

CH

1

6-16

OCF3

H

MeCO

CH

1

6-17

OH

H

MeCO

CH

1

6-18

SH

H

MeCO

CH

1

6-19

NH2

H

MeCO

CH

1

6-20

NHCOMe

H

MeCO

CH

1

6-21

NHCO2Me

H

MeCO

CH

1

6-22

NHCO2CH2CCl3

H

MeCO

CH

1

6-23

Br

H

MeCO

CH

2

6-24

Br

H

EtCO

CH

1

6-25

Br

H

N-PrCO

CH

1

6-26

Br

H

Iso-PrCO

CH

1

6-27

Br

H

Uncle-BuCO

CH

1

6-28

Br

H

CF3CO

CH

1

6-29

Br

H

PhCO

CH

1

6-30

Br

H

2-pyridyl CO

CH

1

6-31

Br

H

3-pyridyl CO

CH

1

6-32

Br

H

4-pyridyl CO

CH

1

6-33

Br

H

2-F-PhCO

CH

1

6-34

Br

H

3-F-PhCO

CH

1

Numbering

Y

R ¹

R ²

R ⁴

A

n

6-35

Br

H

4-F-PhCO

CH

1

6-36

Br

H

2-Cl-PhCO

CH

1

6-37

Br

H

3-Cl-PhCO

CH

1

6-38

Br

H

4-Cl-PhCO

CH

1

6-39

Br

H

2-Br-PhCO

CH

1

6-40

Br

H

2-Me-PhCO

CH

1

6-41

Br

H

Vinyl CO

CH

1

6-42

Br

H

HCCCO

CH

1

6-43

Br

H

MeSO2

CH

1

6-44

Br

H

CF3SO2

CH

1

6-45

Br

H

MeHNCO

CH

1

6-46

Br

H

Me2NCO

CH

1

6-47

Br

H

MeOC(＝O)

CH

1

6-48

Br

H

MeSC(＝O)

CH

1

6-49

Br

H

MeCS

CH

1

6-50

Br

H

MeON(Me)CO

CH

1

6-51

Br

Me

H

MeCO

CH

1

6-52

Br

Me

H

MeCO

N

1

Table 8

Numbering

(X)l

R

R ¹

R ²

R ⁴

R ³

A

n

7-1

3,5-, bis-Cl

CF3

H

MeCO

H

CH

1

7-2

3,5-, bis-Cl

CF3

H

MeCO

CH

1

7-3

3,5-, bis-Cl

CF3

H

MeCO

2-pyridyl CO

CH

1

7-4

3,5-, bis-Cl

CF3

H

HCO

2-pyridyl CH2

CH

1

7-5

3,5-, bis-Cl

CF3

H

MeCO

2-pyridyl CH2

CH

1

7-6

3,5-, bis-Cl

CF3

H

EtCO

2-pyridyl CH2

CH

1

7-7

3,5-, bis-Cl

CF3

H

Me2NCO

2-pyridyl CH2

CH

1

7-8

3,5-, bis-Cl

CF3

H

MeSO2

2-pyridyl CH2

CH

1

7-9

3,5-, bis-Cl

CF3

H

2-pyridyl CO

2-pyridyl CH2

CH

1

7-10

3,5-, bis-Cl

CF3

CN

H

MeCO

H

CH

1

7-11

3,5-, bis-Cl

CF3

CN

H

MeCO

2-pyridyl CH2

CH

1

7-12

3,5-, bis-Cl

CF3

H

HCO

H

CH

1

7-13

3,5-, bis-Cl

CF3

H

MeCO

3-pyridyl CH2

CH

1

7-14

3,5-, bis-Cl

CF3

H

MeCO

4-pyridyl CH2

CH

1

7-15

3,5-, bis-Cl

CF3

H

MeCO

Benzyl

CH

1

7-16

3,5-, bis-Cl

CF3

H

EtCO

H

CH

1

7-17

3,5-, bis-Cl

CF3

H

N-PrCO

H

CH

1

7-18

3,5-, bis-Cl

CF3

H

Iso-PrCO

H

CH

1

7-19

3,5-, bis-Cl

CF3

H

Ring-type-PrCO

H

CH

1

7-20

3,5-, bis-Cl

CF3

H

Uncle-BuCO

H

CH

1

7-21

3,5-, bis-Cl

CF3

H

CF3CO

H

CH

1

Numbering

(X)l

R

R ¹

R ²

R ⁴

R ³

A

n

7-66

3,5-, bis-Cl

CF3

H

MeCO

N＝CMe2

CH

1

7-67

3,5-, bis-Cl

CF3

H

MeCO

OH

CH

1

7-68

3,5-, bis-Cl

CF3

H

MeCO

MeO

CH

1

7-69

3,4-, bis-Cl

CF3

H

MeCO

H

CH

1

7-70

3,4,5-, tri-Cl

CH3

H

MeCO

H

CH

1

7-71

3,4,5-, tri-Cl

CH3

H

Ring-type-PrCO

H

CH

1

7-72

3,4,5-, tri-Cl

CH3

H

CF3CH2CO

H

CH

1

7-73

3,5-, bis-Cl-4-Me

CH3

H

MeCO

H

CH

1

7-74

3-F

CH3

H

MeCO

H

CH

1

7-75

3-Cl

CF3

H

MeCO

H

CH

1

7-76

3-CF3

CF3

H

MeCO

H

CH

1

7-77

4-CF3

CF3

H

MeCO

H

CH

1

7-78

3,5-, bis-CF3

CF3

H

MeCO

H

CH

1

7-79

3-NO2

CF3

H

MeCO

H

CH

1

7-80

3,5-, bis-Cl

CF3

H

MeCO

H

N

1

7-81

3-CH3

CF3

H

MeCO

H

CH

1

7-82

3-CH3O

CF3

H

MeCO

H

CH

1

7-83

3-CN

CF3

H

MeCO

H

CH

1

7-84

3-CF3O

CF3

H

MeCO

H

CH

1

7-85

3-CH3S

CF3

H

MeCO

H

CH

1

7-86

3-CH3S(O)

CF3

H

MeCO

H

CH

1

7-87

3-CH3S(O)2

CF3

H

MeCO

H

CH

1

7-88

3-CF3S

CF3

H

MeCO

H

CH

1

7-89

3-CF3S(O)

CF3

H

MeCO

H

CH

1

7-90

3-CF3S(O)2

CF3

H

MeCO

H

CH

1

7-91

3-OH

CF3

H

MeCO

H

CH

1

7-92

3-SH

CF3

H

MeCO

H

CH

1

7-93

3-NH2

CF3

H

MeCO

H

CH

1

7-94

3-NHCOCH3

CF3

H

MeCO

H

CH

1

7-95

3-NHCOCF3

CF3

H

MeCO

H

CH

1

7-96

3-NHCO2CH3

CF3

H

MeCO

H

CH

1

7-97

3-NHCO2CH2CCl3

CF3

H

MeCO

H

CH

1

7-98

3-NHSO2CH3

CF3

H

MeCO

H

CH

1

7-99

3-NHSO2CF3

CF3

H

MeCO

H

CH

1

7-100

3,5-, bis-Cl

CF3

H

MeCO

H

CH

2

7-101

3,5-, bis-Br

CF3

H

MeCO

H

CH

1

7-102

3,5-, bis-Br

CF3

H

EtCO

H

CH

1

7-103

3,4,5-, tri-Cl

CF3

H

MeCO

H

CH

1

7-104

3,4,5-, tri-Cl

CF3

H

EtCO

H

CH

1

7-105

3,4,5-, tri-Cl

CF3

H

CF3CH2CO

H

CH

1

7-106

3,4,5-, tri-F

CF3

H

MeCO

H

CH

1

7-107

3,4,5-, tri-F

CF3

H

EtCO

H

CH

1

7-108

3,4,5-, tri-Br

CF3

H

MeCO

H

CH

1

7-109

3,4,5-, tri-Br

CF3

H

EtCO

H

CH

1

Numbering

(X)l

R

R ¹

R ²

R ⁴

R ³

A

n

7-110

3,5-, bis-Cl, 4-Br

CF3

H

MeCO

H

CH

1

7-111

3,5-, bis-Cl, 4-Br

CF3

H

EtCO

H

CH

1

7-112

3,5-, bis-Br, 4-Cl

CF3

H

MeCO

H

CH

1

7-113

3,5-, bis-Br, 4-Cl

CF3

H

EtCO

H

CH

1

7-114

3,5-, bis-Cl, 4-I

CF3

H

MeCO

H

CH

1

7-115

3,5-, bis-Cl, 4-I

CF3

H

EtCO

H

CH

1

7-116

3,5-, bis-I

CF3

H

MeCO

H

CH

1

7-117

3,5-, bis-I

CF3

H

EtCO

H

CH

1

7-118

3,5-, bis-Cl, 4-NH2

CF3

H

MeCO

H

CH

1

7-119

3,5-, bis-Cl, 4-NH2

CF3

H

EtCO

H

CH

1

7-120

3,5-, bis-Br, 4-NH2

CF3

H

MeCO

H

CH

1

7-121

3,5-, bis-B r, 4-NH2

CF3

H

EtCO

H

CH

1

7-122

3,5-, bis-I, 4-NH2

CF3

H

MeCO

H

CH

1

7-123

3,5-, bis-I, 4-NH2

CF3

H

EtCO

H

CH

1

7-124

3,5-, bis-Cl, 4-NHAc

CF3

H

MeCO

H

CH

1

7-125

3,5-, bis-Cl, 4-NHAc

CF3

H

EtCO

H

CH

1

7-126

3,5-, bis-Cl, 4-NHCOCF3

CF3

H

MeCO

H

CH

1

7-127

3,5-, bis-Cl, 4-NHCOCF3

CF3

H

EtCO

H

CH

1

7-128

3,4-, bis-Cl, 5-CF3

CF3

H

MeCO

H

CH

1

7-129

3,4-, bis-Cl, 5-CF3

CF3

H

EtCO

H

CH

1

7-130

3,5-, bis-Cl, 4-CF3

CF3

H

MeCO

H

CH

1

7-131

3,5-, bis-Cl, 4-CF3

CF3

H

EtCO

H

CH

1

7-132

3-Cl，5-CF3

CF3

H

MeCO

H

CH

1

7-133

3-Cl，5-CF3

CF3

H

EtCO

H

CH

1

7-134

3-Cl，4-CF3

CF3

H

MeCO

H

CH

1

7-135

3-Cl，4-CF3

CF3

H

EtCO

H

CH

1

7-136

3-Br，5-CF3

CF3

H

MeCO

H

CH

1

7-137

3-Br，5-CF3

CF3

H

EtCO

H

CH

1

7-138

3-Br，4-CF3

CF3

H

MeCO

H

CH

1

7-139

3-Br，4-CF3

CF3

H

EtCO

H

CH

1

7-140

3-I，5-CF3

CF3

H

MeCO

H

CH

1

7-141

3-I，5-CF3

CF3

H

EtCO

H

CH

1

7-142

3-CF3，4-F

CF3

H

MeCO

H

CH

1

7-143

3-CF3，4-F

CF3

H

EtCO

H

CH

1

7-144

3-Cl，5-SCF3

CF3

H

MeCO

H

CH

1

7-145

3-Cl，5-SCF3

CF3

H

EtCO

H

CH

1

7-146

4-NH2

CF3

H

MeCO

H

CH

1

7-147

4-NH2

CF3

H

EtCO

H

CH

1

7-148

4-NH2

CF3

H

CF3CH2CO

H

CH

1

7-149

3-Cl，4-SCF3

CF3

H

MeCO

H

CH

1

7-150

3-Cl，4-SCF3

CF3

H

EtCO

H

CH

1

Table 9

biological test embodiment 1-for the test of Spodoptera litura larvae

Solvent: 3 weight part dimethyl formamides

Emulsifying agent: 1 weight part polyoxyethylene alkyl phenyl ether

For preparing suitable active agent preparations, by the solvent containing above-mentioned amount emulsifying agent of 1 weight part active compound and above-mentioned amount, and this mixed solution is diluted with water to prescribed concentration.

Sweet potato (sweet potate) leaf is immersed in the reagent agent that is diluted with water to prescribed concentration, air-dry, and put into the ware that diameter is 9cm.10 three prodenia litura in age (Spodoptera litura) larvas are put into this ware and leave the indoor of 25 DEG C of constant temperature in.After 2 days and 4 days, add more Rhizoma Dioscoreae esculentae leaf, thereby and counted afterwards at 7 days dead larva number calculate mortality ratio.In this test, every group of test-results is the mean value of the result of two wares.

Be numbered 1-1, 1-2, 1-4, 1-6, 1-11, 1-12, 1-13, 1-15, 1-16, 1-17, 1-19, 1-20, 1-21, 1-23, 1-24, 1-25, 1-26, 1-27, 1-28, 1-31, 1-32, 1-34, 1-35, 1-36, 1-38, 1-40, 141, 1-43, 1-44, 1-46, 1-56, 1-57, 1-58, 1-59, 1-60, 1-61, 1-62, 1-63, 1-90, 1-94, 1-97, 1-98, 1-99, the compounds of this invention of 1-100 and 1-101 demonstrates 100% mortality ratio under 100ppm activity compound concentration.

biological test embodiment 2-for the test (spray testing) of Tetranychus urticae

Solvent: 3 weight part dimethyl formamides

Emulsifying agent: 1 weight part polyoxyethylene alkyl phenyl ether

The one-tenth mite of 50-100 Tetranychus urticae (Tetranychus urticae) is connected on the leaf that is planted in two leaf phase Kidney beans in the basin that diameter is 6cm.After 1 day, with the active compound of the enough prescribed concentration of gun spraying through dilute aqueous solution.After spraying, this basin is deposited to 7 days in greenhouse, and uses following evaluation criteria to calculate acaricidal rate:

Acaricidal rate
		100	All acarids of access are all dead
98	1-4 acarid survival/breeding
		90	5-20 acarid survival/breeding
60	Many acarid survival/breedings, but be less than undressed control group, observe some dead volumes
		0	Do not observe the difference with undressed control group

The compounds of this invention that is numbered 1-1,1-2,1-6,1-11,1-12,1-13,1-15,1-16,1-17,1-19,1-20,1-21,1-24,1-26,1-27,1-28,1-31,1-33,1-34,1-35,1-36,1-38,1-40,1-41,1-44,1-46,1-57,1-58,1-59,1-61,1-62,1-63,1-90,1-93,1-94,1-99,1-101 and 1-102 demonstrates the acaricidal rate that is greater than 98 under 100ppm activity compound concentration.

biological test embodiment 3-for the test of aulacophora femoralis

Solvent: 3 weight part dimethyl formamides

Emulsifying agent: 1 weight part polyoxyethylene alkyl phenyl ether

The leaf of cucumber is immersed in the prescribed concentration to prepare with mode identical in above-mentioned test active compound in dilute aqueous solution, air-dry, and put into the plastic cup containing sterilizing black earth.Then 5 two aulacophora femoralis in age (Aulacophora femoralis) larvas are put into this cup.After 7 days, thereby count the number calculating mortality ratio of dead larva.

Be numbered 1-1, 1-2, 1-6, 1-11, 1-12, 1-13, 1-15, 1-16, 1-17, 1-19, 1-20, 1-21, 1-23, 1-24, 1-26, 1-27, 1-28, 1-31, 1-32, 1-33, 1-34, 1-35, 1-36, 1-38, 1-40, 1-41, 1-44, 1-46, 1-57, 1-58, 1-59, 1-60, 1-61, 1-62, 1-63, 1-93, 1-94, 1-97, 1-98, 1-99, 1-100, 1-101, the compounds of this invention of 1-102 and 1-106 demonstrates 100% mortality ratio under 100ppm activity compound concentration.

biological test embodiment 4-for the test of black peach aphid with organophosphorus medicament and carbamate medicament resistance

Solvent: 3 weight part dimethyl formamides

Emulsifying agent: 1 weight part polyoxyethylene alkyl phenyl ether

The adult of the black peach aphid (Myzus persicae) with organophosphorus medicament and carbamate medicament resistance is connected on the leaf of the two leaf stage eggplant in the basin that cultivation is 6cm at diameter, and every strain rice shoot is inoculated approximately 30 to 50.Inoculate latter 1 day, with the enough active compounds with the prescribed concentration prepared with mode identical in above-mentioned test of gun spraying through dilute aqueous solution.After spraying, this basin is deposited 7 days in the greenhouse of 28 DEG C, calculated mortality ratio.Repeat this test.

As specific examples, the above-claimed cpd that is numbered 1-31 and 1-61 demonstrates 100% mortality ratio under the activity compound concentration of 500ppm.

biological test embodiment 5-1-for the test of ctenocephalides felis

Solvent: dimethyl formamide

For preparing suitable active agent preparations, 10mg active compound is dissolved in the above-mentioned solvent of 0.5mL, and this mixed solution is diluted to prescribed concentration with animal blood.

An about 10-15 ctenocephalides felis (Ctenocephalides felis) adult is put into a flea special container.Comprise that by containing as above the laboratory film for another container [PARAFILM (trade mark)] of the described blood solution of the compound of preparation covers.Container containing blood is inverted and is placed on this flea special container.This system makes ctenocephalides felis can suck the blood in this container.This blood solution is deposited at 37 DEG C, and this flea special container is at room temperature deposited.After specific for some time, calculate the mortality ratio of ctenocephalides felis.For this test, it is all dead that 100% mortality ratio means all ctenocephalides felis, and 0% mortality ratio means all ctenocephalides felis and all survives.

In this biological test, compound 1-64 demonstrates the mortality ratio that is greater than 80% under 100ppm activity component concentration.

biological test embodiment-5-2-for the test of ctenocephalides felis

Solvent: methyl-sulphoxide

For preparing suitable active agent preparations, 10mg active compound is dissolved in 0.5mL solvent, and this dope is diluted to desired concn with ox blood.

The adult (ctenocephalides felis (Ctenocephalides felis)) that about 10-15 head is not sucked blood is put into flea chamber.In blood chamber to bottom with sealed membrane sealing, pack into containing the ox blood of compound solution and be placed on top, flea chamber, thereby making flea can suck this blood.Blood chamber is heated to 37 DEG C, and this flea chamber is at room temperature deposited.

After the time period of specifying, determine the mortality ratio in %.100% means all fleas is all killed; 0% means not have flea to be killed.

In this test, the compound of for example following Preparation Example demonstrates under 100ppm rate of application >=80% excellent activity:

Embodiment numbers 1-1,1-5,1-6,1-12,1-13,1-15,1-16,1-19,1-20,1-21,1-23,1-24,1-25,1-26,1-27,1-28,1-31,1-33,1-34,1-35,1-36,1-38,1-40,1-41,1-42,1-44,1-46,1-57,1-58,1-59,1-60,1-61,1-63,1-64,1-93,1-94,1-98,1-101,7-1,1-128,1-129,1-131,1-140,2-2.

biological test embodiment 6-1-for the test (injection) of boophilus microplus

Solvent: dimethyl formamide

For preparing suitable active agent preparations, 10mg active compound is dissolved in the above-mentioned solvent of 0.5mL, and this mixture is diluted with water to prescribed concentration.

The compound solution of as above preparation is injected to the belly of 5 female boophilus micropluses of fully sucking blood (Boophilus microplus) adult.These boophilus micropluses are transferred in replica ware (replica dish) and in incubator, deposited specific for some time.

After specific for some time, calculate the mortality ratio of boophilus microplus.In this test, it is all dead that 100% mortality ratio means all boophilus micropluses, and 0% mortality ratio means all boophilus micropluses and all survives.

In above-mentioned this biological test, compound 1-64 demonstrates the mortality ratio that is greater than 80% in the time of the activeconstituents dosage of 20ug/ animal.

biological test embodiment 6-2-for the test (injection) of boophilus microplus

Solvent: methyl-sulphoxide

For preparing suitable active agent preparations, 10mg active compound is dissolved in 0.5mL solvent, and this dope is diluted with water to desired concn.

Compound solution is injected to the belly of 5 female ticks of being satiated with food (boophilus microplus (Boophilusmicroplus)) adult.Tick is transferred in replica ware and in the controlled environment chamber and cultivated for some time.

After one period of fixed time, determine the mortality ratio in %.100% to mean all ovum all sterile; 0% means all ovum all can educate.

In this test, the compound of for example following Preparation Example demonstrates in the time of the rate of application of 20 μ g/ animals >=80% excellent activity:

Embodiment numbers 1-1, 1-5, 1-6, 1-12, 1-13, 1-15, 1-16, 1-19, 1-20, 1-21, 1-22, 1-23, 1-24, 1-25, 1-26, 1-27, 1-28, 1-31, 1-32, 1-33, 1-34, 1-35, 1-36, 1-37, 1-38, 1-40, 1-41, 1-42, 1-43, 1-44, 1-46, 1-57, 1-58, 1-59, 1-60, 1-61, 1-63, 1-64, 1-79, 1-93, 1-94, 1-98, 1-99, 1-100, 1-101, 1-102, 1-106, 1-128, 1-129, 1-131, 1-133, 1-140, 2-2, 2-3, 2-4, 2-5, 2-6, 2-46, 2-47, 2-54, 7-1.

biological test embodiment 7-1-for the test of lucilia cuprina

Solvent: dimethyl formamide

For preparing suitable active agent preparations, 10mg active compound is dissolved in the above-mentioned solvent of 0.5mL, and this mixed solution is diluted with water to prescribed concentration.

An about 20-30 lucilia cuprina (Lucillia cuprina) larva is put into one containing 1cm ³in the test tube of the compound water solution that broken horseflesh and 0.5mL are as above prepared.

After specific for some time, calculate the mortality ratio of lucilia cuprina.For this test, it is all dead that 100% mortality ratio means all lucilia cuprinas, and 0% mortality ratio means all lucilia cuprinas and all survives.

In this biological test, compound 1-64 demonstrates the mortality ratio that is greater than 80% in the time of 100ppm activity component concentration.

biological test embodiment 7-2-for the test of lucilia cuprina

Solvent: methyl-sulphoxide

An about 20-30 lucilia cuprina (Lucillia cuprina) larva is transferred in a test tube containing the water diluent of the broken horseflesh of 1cm3 and 0.5mL test compound.

Specifying after for some time, calculate the mortality ratio in %.100% means all death of all larvas; 0% means to be killed without larva.

In this test, the compound of for example following Preparation Example demonstrates in the time of the rate of application of 100ppm >=80% excellent activity:

Embodiment numbers 1-1, 1-5, 1-6, 1-12, 1-13, 1-15, 1-16, 1-19, 1-20, 1-21, 1-23, 1-24, 1-25, 1-26, 1-27, 1-28, 1-31, 1-32, 1-33, 1-34, 1-35, 1-36, 1-37, 1-38, 1-40, 1-41, 1-42, 1-43, 1-44, 1-46, 1-57, 1-58, 1-59, 1-60, 1-61, 1-63, 1-64, 1-93, 1-94, 1-98, 1-101, 1-129, 1-131, 1-140, 2-2, 2-5, 2-6, 2-46, 2-47, 7-1.

biological test embodiment 8-1-for the test of housefly

Solvent: dimethyl formamide

For preparing suitable active agent preparations, 10mg active compound is dissolved in the above-mentioned solvent of 0.5mL, and gained mixed solution is diluted with water to prescribed concentration.

In the preparatory stage, by sugar with in the sponge of the mixture suction intended size of the aqueous solution of the compound of as above preparing, and this sponge is put into a test chamber.10 boss fly (Muscadomestica) adults are put into this container, and by the cap covers of boring a hole for this container.

After specific for some time, calculate the mortality ratio of housefly.In this test, it is all dead that 100% mortality ratio means all houseflies, and 0% mortality ratio means all houseflies and all survives.

biological test embodiment 8-2-for the test of housefly

Solvent: methyl-sulphoxide

Before test, a slice kitchen sponge is soaked with the mixture of sugar and compound solution, and this sponge is put into a container.10 boss flies (Musca domestica) adult is put into this container the closed with covers with perforation.

Specifying after for some time, determine the mortality ratio in %.100% means all houseflies is all killed; 0% means to be killed without housefly.

Embodiment numbers 1-1,1-6,1-12,1-13,1-15,1-16,1-19,1-20,1-21,1-23,1-26,1-36,1-38,1-40,1-41 ,-42,1-44,1-46,1-57,1-58,1-59,1-60,1-61,1-63,1-64,1-79,1-94,1-99,1-101,1-129,1-131,1-140,2-5,7-1.

biological test embodiment 9-for the test (dipping) of boophilus microplus

Solvent: methyl-sulphoxide

The female boophilus microplus (Boophilus microplus) that 8-10 head is satiated with food becomes tick put into the plastic beaker of perforation and flood 1 minute at compound water solution.This tick is transferred on the filter paper in plastic pallet.Within 7 days, monitor afterwards the situation of laying eggs of zygote.

Specifying after for some time, determine the mortality ratio in %.100% means all tick worms is killed; 0% means to be killed without tick worm.

Embodiment numbers 1-4,7-1,1-12,1-13,1-16,1-19,1-20,1-21,1-24,1-27,1-28,1-31,1-33,1-40,1-41,1-42,1-44,1-57,1-58,1-59,1-60,1-63,1-64,1-94,1-99,1-101,1-129,1-131,1-133,1-140.

biological test embodiment 10-spend the test of tick for Hebrew

Solvent: methyl-sulphoxide

For preparing suitable active agent preparations, by the solvent of 1 weight part active compound and described amount, and this dope is released to desired concn with contained solvent.

Spend the nymph of tick (Amblyomma hebraeum) put into the plastic beaker of perforation and flood 1 minute at compound water solution Hebrew.This tick is transferred on the filter paper in culture dish and in the controlled environment chamber and is cultivated 42 days.

Embodiment numbers 1-13,1-19,1-20,1-44,1-58,1-59,1-101.

biological test embodiment 11-for the drug effect of the Ctenocephalides felis felis on cat (cat flea)

In research, in the time of first 4 days of processing and 1 day, with approximately 100 not Ctenocephalides felis felis (the Ctenocephalides felis felis) adults of feed cat is infected.Ctenocephalides felis is placed on the neck fur of cat.

In research 0 day time, by counting cat with it the number of this flea check infection rate.The number of record flea alive.

After this flea is counted, use studied product to process cat.The cat of control group is not processed and as negative control group.Studied veterinary products is carried out to single-point (one spot) percutaneous drug delivery with the dose volume of 0.1-0.2ml/kg body weight.Described processing is only carried out 1 time in the time studying 0 day.Only healthy cat is processed and included in research.

In the time of research 1 day and/or 2 days, flea is counted, wherein cat is carried out to combing the record flea number of living.Preserve acquired results.

Weekly, every cat is infected with approximately 100 ctenocephalides felis adults of not taking food again.Infect again latter 1 day and/or 2 days to, cat is carried out combing and counts the flea number alive of every cat.Record acquired results.

Processing and at weekly 24h to 48h after infecting again, if drug effect can reach > 95%, thinking that this activeconstituents height is effective.Drug effect should provide through the time in 3-4 week.

For the calculating of drug effect, use improved Abbott formula:

CG: control group

TG: treatment group

Carry out the activeconstituents 1-129 of point type (Spot-on) administration with the dosage of 0.1ml/kg (15mg/kg), Ctenocephalides felis felis cat flea is there is to the high-drug-effect of > 95%.

biological test embodiment 12-for the drug effect of the tick worm (castor bean tick) on cat

Under study for action, process first 4 days and/or 1 day, make cat calmness with the binding substances of active ingredient hydrochloric acid ketamine (ketaminhydrochloride) and acetypromazin maleate (acepromazinmaleat).After all cat calmness (after about 10-15 minute), all cats are put into single cage and 50 castor bean ticks (Ixodes ricinus ticks) (25 female and 25 male) are placed on the back fur of cat.Make sleep about 1h-1.5h stop its reason hair and remove this tick worm of cat.

, cat is placed on check-out console to check the infection rate of tick worm 0 day time in first 3 days of research or research.Emphasis checks region between head, ear, eye, neck and the sidepiece of health and the neighboring area of veutro portion and toe.Count and record the number of the tick worm alive of being satiated with food adhering to.Remove dead tick worm.

In the time studying 0 day, to after tick worm counting, it is processed.The cat of control group is not processed and as negative control group.Studied veterinary products single-point is administered to the skin of head base portion.Described processing was only carried out once in the time of 0 day.Only the cat of clinical health is included in research.

Tick worm being counted in the 1st day and/or 2 days of research, and count and record survive or death adhere to tick borer population order.At the 2nd day, remove all survivals and dead tick worm.

Weekly, every 50 castor bean tick for cat (25 female and 25 male) infect, and 1 day and/or 2 days after infecting counts tick worm again.And count and record survival and dead adhere to tick worm.Infect again latter 2 days, remove all tick worms.

Processing and at weekly 48h after infecting again, if drug effect can reach > 90%, thinking that this activeconstituents height is effective.Drug effect should provide through the time in 3-4 week.

For the calculating of drug effect, use improved Abbott formula:

CG: control group

TG: treatment group

Carry out the activeconstituents 1-129 of point type administration with the dosage of 0.1ml/kg (15mg/kg), castor bean tick is there is to the high-drug-effect of > 90%.

example of formulations 1 (granule)

In the mixture containing 10 parts of the compounds of this invention (numbering 1-1), 30 parts of wilkinites (polynite), 58 parts of talcums and 2 parts of Sulfite lignin; add 25 parts of water; this mixture is fully mixed to merga pass Squeezinggranulator through the granulation of 10-40 sieve mesh; dry at the temperature of 40-50 DEG C, obtain granule.

example of formulations 2 (granule)

The clay mineral grain of 95 (95) parts of size distribution within the scope of 0.2 to 2mm put into impeller.In mixing tank rotary course, 5 parts of the compounds of this invention (numbering 1-2) are sprayed together with liquid diluent, evenly wetting, and dry at the temperature of 40-50 DEG C, obtain granule.

example of formulations 3 (missible oil)

30 (30) parts of the compounds of this invention (numbering 1-13), 55 parts of dimethylbenzene, 8 parts of polyoxyethylene alkyl phenyl ethers and 7 parts of alkyl benzene calcium sulfonates are mixed and stirred, obtain a kind of missible oil.

example of formulations 4 (wettable powder)

Ten five (15) parts of the compounds of this invention (numbering 1-13), 80 parts of white carbon(ink)s (hydration amorphous silicon oxide fine powder) and the mixture of powdered clay (1: 5), 2 parts of sodium alkyl benzene sulfonates and 3 parts of sodium alkyl naphthalene sulfonate-formalin condensess are mixed together, pulverize and mix, obtaining a kind of wettable powder.

example of formulations 5 (water dispersible granules)

The diatomite of 20 (20) parts of the compounds of this invention (numbering 1-1), 30 parts of sodium lignosulfonates, 15 parts of wilkinites and 35 parts of calcinings is fully mixed, and adding after water, extrude with the sieve of 0.3mm, and dry, obtain a kind of water dispersible granules.

Industrial applicability:

New aryl isoxazoline derivatives of the present invention has good killing insect and kill acarid activity as insecticide and/or miticide, as shown here.

Claims

1. the aryl isoxazoline derivatives of following formula:

example 1-16 example 1-17 example 7-103

example 7-128.

2. insect-killing composition, the compound that it contains at least one claim 1.

3. the compound of claim 1 is for the preparation of the purposes of pharmaceutical composition that is administered to animal.

4. the method for the control animal nuisance of non-therapeutic purpose, is characterized in that the aryl isoxazoline derivatives of claim 1 to be applied to animal nuisance and/or its habitat.

5. the aryl isoxazoline derivatives of claim 1 is used for the purposes of the non-therapeutic purpose of preventing and treating animal nuisance.

6. the aryl isoxazoline derivatives of claim 1 is for the preparation of the purposes of the pharmaceutical composition for preventing and treating animal nuisance.

7. the aryl isoxazoline derivatives of claim 1 is for the treatment of the purposes of seed.

8. the aryl isoxazoline derivatives of claim 1 is for the treatment of the purposes of transgenic plant.