CN105218557A

CN105218557A - A kind of substituted thienopyrimidine-4 aminated compounds and application thereof with pesticide and miticide actility

Info

Publication number: CN105218557A
Application number: CN201410318199.2A
Authority: CN
Inventors: 柴宝山; 张金波; 宋玉泉; 杨吉春; 李轲轲; 王立增; 孙旭峰; 刘长令
Original assignee: Shenyang Research Institute of Chemical Industry Co Ltd; Sinochem Corp
Current assignee: Shenyang Sinochem Agrochemicals R&D Co Ltd
Priority date: 2014-07-04
Filing date: 2014-07-04
Publication date: 2016-01-06
Anticipated expiration: 2034-07-04
Also published as: CN105218557B

Abstract

The invention discloses the application of a kind of substituted thienopyrimidine-4 aminated compounds as shown in general formula I as Insecticidal and acaricidal agent,

Description

A kind of substituted thienopyrimidine-4 aminated compounds and application thereof with pesticide and miticide actility

Technical field

The invention belongs to agricultural insecticidal, miticide field.Relate to a kind of substituted thienopyrimidine-4 aminated compounds and the application thereof with pesticide and miticide actility particularly.

Background technology

Report the compound 1 shown in following general formula in patent US2007093498 and representation compound KC1 has fungicidal activity, but do not have desinsection, acaricidal activity to report:

The compound 2 shown in following general formula is reported and representation compound KC2, KC3 have insecticidal activity in patent CN101453895:

Patent US20060089370 discloses following compound formula and particular compound KC4 (being numbered compound 5a in patent), under 200ppm dosage, has good fungicidal activity:

Patent WO2007046809 and US2007093498 also discloses following compound K C5 and KC6, has good fungicidal activity:

Although compound and the compounds of this invention have certain similarity disclosed in this patent, still there is significant difference in structure or purposes.

Summary of the invention

The object of the present invention is to provide a kind of substituted thienopyrimidine-4 aminated compounds and the application thereof with pesticide and miticide actility.

For achieving the above object, the present invention adopts technical scheme to be:

There is the substituted thienopyrimidine-4 aminated compounds of pesticide and miticide actility, as shown in general formula I:

In formula:

R ₁, R ₂be selected from hydrogen, halogen, cyano group, nitro, C respectively ₁-C ₁₂alkyl or halo C ₁-C ₁₂alkyl;

Or R ₁and R ₂saturated or unsaturated 3-6 unit's carbocyclic ring or heterocycle is formed together, without to replace or optional by halogen, C on described carbocyclic ring or heterocycle with the carbon atom that is attached thereto ₁-C ₁₂alkyl, halo C ₁-C ₁₂alkyl, C ₁-C ₁₂alkoxyl group or halo C ₁-C ₁₂alkoxyl group replaces;

R ₃be selected from hydrogen, halogen, C ₁-C ₁₂alkyl or halo C ₁-C ₁₂alkyl;

R ₄be selected from hydrogen, C ₁-C ₁₂alkyl or halo C ₁-C ₁₂alkyl;

R ₅, R ₆be selected from hydrogen, halogen, cyano group, nitro, C respectively ₁-C ₁₂alkyl, halo C ₁-C ₁₂alkyl, C ₁-C ₁₂alkoxyl group, halo C ₁-C ₁₂alkoxyl group, C ₃-C ₁₂cycloalkyl, halo C ₃-C ₁₂cycloalkyl, C ₁-C ₁₂alkylamino, halo C ₁-C ₁₂alkylamino, C ₂-C ₁₂dialkyl amido, C ₁-C ₁₂alkylthio, halo C ₁-C ₁₂alkylthio, C ₁-C ₁₂alkyl sulphonyl, halo C ₁-C ₁₂alkyl sulphonyl, C ₁-C ₁₂alkyl-carbonyl, halo C ₁-C ₁₂alkyl-carbonyl, C ₁-C ₁₂alkoxy carbonyl, C ₁-C ₁₂alkoxy C ₁-C ₁₂alkyl, halo C ₁-C ₁₂alkoxy C ₁-C ₁₂alkyl or C ₁-C ₁₂alkoxy carbonyl C ₁-C ₁₂alkyl;

G ₁be selected from CR ₇or N; G ₂be selected from CR ₈or N; G ₃be selected from CR ₉or N; But G ₁, G ₂, G ₃can not be N simultaneously;

R ₇, R ₈, R ₉be selected from hydrogen, halogen, cyano group, nitro, C respectively ₁-C ₁₂alkyl, halo C ₁-C ₁₂alkyl, C ₁-C ₁₂alkoxyl group, halo C ₁-C ₁₂alkoxyl group, C ₃-C ₁₂cycloalkyl, halo C ₃-C ₁₂cycloalkyl, C ₁-C ₁₂alkylamino, halo C ₁-C ₁₂alkylamino, C ₂-C ₁₂dialkyl amido, C ₁-C ₁₂alkylthio, halo C ₁-C ₁₂alkylthio, C ₁-C ₁₂alkyl sulphonyl, halo C ₁-C ₁₂alkyl sulphonyl, C ₁-C ₁₂alkyl-carbonyl, halo C ₁-C ₁₂alkyl-carbonyl, C ₁-C ₁₂alkoxy carbonyl, C ₁-C ₁₂alkoxy C ₁-C ₁₂alkyl, halo C ₁-C ₁₂alkoxy C ₁-C ₁₂alkyl or C ₁-C ₁₂alkoxy carbonyl C ₁-C ₁₂alkyl;

Or the salt of compound of Formula I.

Above-mentioned when there is the substituted thienopyrimidine-4 aminated compounds of pesticide and miticide actility more preferably compound be: in general formula I

R ₁, R ₂be selected from hydrogen, halogen, cyano group, nitro, C respectively ₁-C ₈alkyl or halo C ₁-C ₈alkyl;

Or R ₁and R ₂saturated or unsaturated 3-6 unit's carbocyclic ring or heterocycle is formed together, without to replace or optional by halogen, C on described carbocyclic ring or heterocycle with the carbon atom that is attached thereto ₁-C ₈alkyl, halo C ₁-C ₈alkyl, C ₁-C ₈alkoxyl group or halo C ₁-C ₈alkoxyl group replaces;

R ₃be selected from hydrogen, halogen, C ₁-C ₈alkyl or halo C ₁-C ₈alkyl;

R ₄be selected from hydrogen, C ₁-C ₈alkyl or halo C ₁-C ₈alkyl;

R ₅, R ₆be selected from hydrogen, halogen, cyano group, nitro, C respectively ₁-C ₈alkyl, halo C ₁-C ₈alkyl, C ₁-C ₈alkoxyl group, halo C ₁-C ₈alkoxyl group, C ₃-C ₈cycloalkyl, halo C ₃-C ₈cycloalkyl, C ₁-C ₈alkylamino, halo C ₁-C ₈alkylamino, C ₂-C ₈dialkyl amido, C ₁-C ₈alkylthio, halo C ₁-C ₈alkylthio, C ₁-C ₈alkyl sulphonyl, halo C ₁-C ₈alkyl sulphonyl, C ₁-C ₈alkyl-carbonyl, halo C ₁-C ₈alkyl-carbonyl, C ₁-C ₈alkoxy carbonyl, C ₁-C ₈alkoxy C ₁-C ₈alkyl, halo C ₁-C ₈alkoxy C ₁-C ₈alkyl or C ₁-C ₈alkoxy carbonyl C ₁-C ₈alkyl;

R ₇, R ₈, R ₉be selected from hydrogen, halogen, cyano group, nitro, C respectively ₁-C ₈alkyl, halo C ₁-C ₈alkyl, C ₁-C ₈alkoxyl group, halo C ₁-C ₈alkoxyl group, C ₃-C ₈cycloalkyl, halo C ₃-C ₈cycloalkyl, C ₁-C ₈alkylamino, halo C ₁-C ₈alkylamino, C ₂-C ₈dialkyl amido, C ₁-C ₈alkylthio, halo C ₁-C ₈alkylthio, C ₁-C ₈alkyl sulphonyl, halo C ₁-C ₈alkyl sulphonyl, C ₁-C ₈alkyl-carbonyl, halo C ₁-C ₈alkyl-carbonyl, C ₁-C ₈alkoxy carbonyl, C ₁-C ₈alkoxy C ₁-C ₈alkyl, halo C ₁-C ₈alkoxy C ₁-C ₈alkyl or C ₁-C ₈alkoxy carbonyl C ₁-C ₈alkyl;

Or the salt of compound of Formula I.

Above-mentioned when there is the substituted thienopyrimidine-4 aminated compounds of pesticide and miticide actility further preferred compound be: in general formula I

R ₁, R ₂be selected from hydrogen, halogen, cyano group, nitro, C respectively ₁-C ₄alkyl or halo C ₁-C ₄alkyl;

Or R ₁and R ₂saturated or unsaturated 3-6 unit's carbocyclic ring or heterocycle is formed together, without to replace or optional by halogen, C on described carbocyclic ring or heterocycle with the carbon atom that is attached thereto ₁-C ₄alkyl, halo C ₁-C ₄alkyl, C ₁-C ₄alkoxyl group or halo C ₁-C ₄alkoxyl group replaces;

R ₃be selected from hydrogen, halogen, C ₁-C ₄alkyl or halo C ₁-C ₄alkyl;

R ₄be selected from hydrogen, C ₁-C ₄alkyl or halo C ₁-C ₄alkyl;

R ₅, R ₆be selected from hydrogen, halogen, cyano group, nitro, C respectively ₁-C ₄alkyl, halo C ₁-C ₄alkyl, C ₁-C ₄alkoxyl group, halo C ₁-C ₄alkoxyl group, C ₃-C ₆cycloalkyl, halo C ₃-C ₆cycloalkyl, C ₁-C ₄alkylamino, halo C ₁-C ₄alkylamino, C ₂-C ₄dialkyl amido, C ₁-C ₄alkylthio, halo C ₁-C ₄alkylthio, C ₁-C ₄alkyl sulphonyl, halo C ₁-C ₄alkyl sulphonyl, C ₁-C ₄alkyl-carbonyl, halo C ₁-C ₄alkyl-carbonyl, C ₁-C ₄alkoxy carbonyl, C ₁-C ₄alkoxy C ₁-C ₄alkyl, halo C ₁-C ₄alkoxy C ₁-C ₄alkyl or C ₁-C ₄alkoxy carbonyl C ₁-C ₄alkyl;

R ₇, R ₈, R ₉be selected from hydrogen, halogen, cyano group, nitro, C respectively ₁-C ₄alkyl, halo C ₁-C ₄alkyl, C ₁-C ₄alkoxyl group, halo C ₁-C ₄alkoxyl group, C ₃-C ₆cycloalkyl, halo C ₃-C ₆cycloalkyl, C ₁-C ₄alkylamino, halo C ₁-C ₄alkylamino, C ₂-C ₄dialkyl amido, C ₁-C ₄alkylthio, halo C ₁-C ₄alkylthio, C ₁-C ₄alkyl sulphonyl, halo C ₁-C ₄alkyl sulphonyl, C ₁-C ₄alkyl-carbonyl, halo C ₁-C ₄alkyl-carbonyl, C ₁-C ₄alkoxy carbonyl, C ₁-C ₄alkoxy C ₁-C ₄alkyl, halo C ₁-C ₄alkoxy C ₁-C ₄alkyl or C ₁-C ₄alkoxy carbonyl C ₁-C ₄alkyl;

Or the salt of compound of Formula I.

R ₁, R ₂be selected from hydrogen, halogen or C respectively ₁-C ₄alkyl;

Or R ₁and R ₂saturated 3-6 unit carbocyclic ring is formed together with the carbon atom be attached thereto;

R ₃be selected from hydrogen;

R ₄be selected from hydrogen or C ₁-C ₄alkyl;

R ₅, R ₆be selected from hydrogen, halogen, cyano group, nitro, C respectively ₁-C ₄alkyl, halo C ₁-C ₄alkyl, C ₁-C ₄alkoxyl group or halo C ₁-C ₄alkoxyl group;

R ₇, R ₈, R ₉be selected from hydrogen, halogen, cyano group, nitro, C respectively ₁-C ₄alkyl, halo C ₁-C ₄alkyl, C ₁-C ₄alkoxyl group or halo C ₁-C ₄alkoxyl group;

Or the hydrochloride of compound of Formula I, vitriol, nitrate, supercarbonate, carbonate, phosphoric acid salt, formate, acetate, trifluoroacetate, benzene sulfonate, tosilate, metilsulfate, benzoate, Citrate trianion, malate, tartrate, maleate, succinate, ascorbate salt or oxalate.

Above-mentioned when there is the substituted thienopyrimidine-4 aminated compounds of pesticide and miticide actility most preferred compound be: in general formula I

R ₁be selected from hydrogen, chlorine or methyl;

R ₂be selected from hydrogen or methyl;

Or R ₁and R ₂saturated 6 yuan of carbocyclic rings are formed together with the carbon atom be attached thereto;

R ₃, R ₄be selected from hydrogen;

R ₅, R ₆be selected from hydrogen, fluorine, chlorine, cyano group, nitro, trifluoromethyl or methoxyl group respectively;

R ₇be selected from hydrogen, fluorine, chlorine, cyano group, nitro or trifluoromethyl;

R ₈be selected from hydrogen, chlorine or methoxyl group;

R ₉be selected from hydrogen, chlorine, bromine, cyano group, nitro, methyl, trifluoromethyl, difluorochloromethyl, seven fluorine sec.-propyls, methoxyl group or isopropoxy.

Above-mentioned its desinsection of substituted thienopyrimidine-4 aminated compounds, the activity of killing mite are remarkable, simultaneously following concrete chemical combination not only desinsection, kill mite activity remarkable, and the novel structure of compound, and then make its activity more remarkable.

Above-mentioned when there is the substituted thienopyrimidine-4 aminated compounds of pesticide and miticide actility concrete preferred compound be: in general formula I

Work as R ₁and R ₂when forming saturated 6 yuan of carbocyclic rings together with the carbon atom be attached thereto,

R ₃, R ₄be selected from hydrogen;

R ₈be selected from hydrogen, chlorine or methoxyl group;

R ₉be selected from hydrogen, chlorine, bromine, cyano group, nitro, methyl, trifluoromethyl, difluorochloromethyl, seven fluorine sec.-propyls, methoxyl group or isopropoxy;

Work as R ₁and R ₂when not becoming ring with the carbon atom that is attached thereto,

R ₁be selected from hydrogen, chlorine or methyl;

R ₂be selected from hydrogen or methyl;

R ₃, R ₄be selected from hydrogen;

G ₁be selected from CR ₇; G ₂be selected from CR ₈; G ₃be selected from CR ₉;

R ₈be selected from hydrogen, chlorine or methoxyl group;

Above-mentioned when having in the substituted thienopyrimidine-4 aminated compounds of pesticide and miticide actility concrete most preferred compound be: in general formula I

R ₁be selected from hydrogen, chlorine or methyl;

R ₂be selected from hydrogen or methyl;

R ₃, R ₄be selected from hydrogen;

R ₅be selected from hydrogen, fluorine or chlorine;

R ₆be selected from hydrogen;

R ₇be selected from hydrogen, fluorine or chlorine;

R ₈be selected from hydrogen;

A kind of compound of Formula I or its salt are used as the purposes preparing Insecticidal and acaricidal agent medicine in agricultural, forestry or health field.

A kind of desinsection, miticide composition, the active ingredient of desinsection, miticide composition is the compound of described formula I, active ingredient and its combine at agriculturally acceptable carrier, and then obtain composition; In composition, the weight percentage of active ingredient is 0.1-99%.

In the definition of the compound of Formula I provided, collect the following substituting group of term general proxy used above:

Halogen: refer to fluorine, chlorine, bromine or iodine.Alkyl: straight or branched alkyl, as methyl, ethyl, propyl group, sec.-propyl, normal-butyl or the tertiary butyl.Cycloalkyl: substituted or unsubstituted cyclic alkyl, as cyclopropyl, cyclopentyl or cyclohexyl.Substituting group is as methyl, halogen etc.Haloalkyl: straight or branched alkyl, the hydrogen atom on these alkyl can partly or entirely replace by halogen atom, as chloromethyl, dichloromethyl, trichloromethyl, methyl fluoride, difluoromethyl, trifluoromethyl, seven fluorine sec.-propyls etc.Alkoxyl group: straight or branched alkyl, is connected in structure through Sauerstoffatom key, as methoxyl group, oxyethyl group.Halogenated alkoxy: straight or branched alkoxyl group, the hydrogen atom on these alkoxyl groups can partly or entirely replace by halogen atom.As chlorine methoxyl group, dichloro methoxyl group, trichloromethoxy, fluorine methoxyl group, difluoro-methoxy, trifluoromethoxy, chlorine fluorine methoxyl group, trifluoro ethoxy etc.Alkylthio: straight or branched alkyl, is connected in structure through sulphur atom key, as methylthio group, ethylmercapto group.Halogenated alkylthio: straight or branched alkylthio, the hydrogen atom on these alkyl can partly or entirely replace by halogen atom.As chloromethane sulfenyl, dichloromethane sulfenyl, trichloro-methylthio, fluorine methylthio group, difluoro methylthio group, trifluoromethylthio, chlorine fluorine methylthio group etc.Alkyl sulphonyl: straight or branched alkyl is through alkylsulfonyl (-SO ₂-) be connected in structure, as methyl sulphonyl.Halogenated alkyl sulfonyl: straight or branched alkyl sulphonyl, the hydrogen atom on its alkyl can partly or entirely replace by halogen atom.Alkylamino: straight or branched alkyl, is connected in structure through nitrogen-atoms key.Haloalkylamino: straight or branched alkylamino, the hydrogen atom on these alkyl can partly or entirely replace by halogen atom.Alkyl-carbonyl: straight or branched alkyl is connected in structure, as formyl radical through carbonyl (-CO-).Halogenated alkyl carbonyl: straight or branched alkyl is connected in structure through carbonyl (-CO-), the hydrogen atom on these alkyl can partly or entirely replace by halogen atom, as fluoroform acyl group.Alkoxy carbonyl: straight or branched alkoxyl group is connected in structure, as CH through carbonyl (-CO-) ₃oCO.

The compound that the present invention can be used as Insecticidal and acaricidal agent is illustrated by the particular compound listed in table 1-28, but does not limit the present invention.

Table 1: in compound 1-1-91, G ₁for C-F, G ₂for CH, G ₃for C-CN, R ₁, R ₂, R ₃, R ₄, R ₅, R ₆(hereinafter referred to as R ₁-R ₆) specifically see the following form.

Table 1

Table 2: in compound of Formula I 2-1-91, G ₁for C-Cl, G ₂for CH, G ₃for C-CN, R ₁-R ₆specifically in table 1.

Table 3: in compound of Formula I 3-1-91, G ₁for CH, G ₂for CH, G ₃for C-CN, R ₁-R ₆specifically in table 1.

Table 4: in compound of Formula I 4-1-91, G ₁for C-F, G ₂for CH, G ₃for C-CF ₃, R ₁-R ₆specifically in table 1.

Table 5: in compound of Formula I 5-1-91, G ₁for C-Cl, G ₂for CH, G ₃for C-CF ₃, R ₁-R ₆specifically in table 1.

Table 6: in compound of Formula I 6-1-91, G ₁for CH, G ₂for CH, G ₃for C-CF ₃, R ₁-R ₆specifically in table 1.

Table 7: in compound of Formula I 7-1-91, G ₁for C-F, G ₂for CH, G ₃for C-NO ₂, R ₁-R ₆specifically in table 1.

Table 8: in compound of Formula I 8-1-91, G ₁for C-Cl, G ₂for CH, G ₃for C-NO ₂, R ₁-R ₆specifically in table 1.

Table 9: in compound of Formula I 9-1-91, G ₁for CH, G ₂for CH, G ₃for C-NO ₂, R ₁-R ₆specifically in table 1.

Table 10: in compound of Formula I 10-1-91, G ₁for CH, G ₂for CH, G ₃for C-CH ₃, R ₁-R ₆specifically in table 1.

Table 11: in compound of Formula I 11-1-91, G ₁for CH, G ₂for CH, G ₃for C-Cl, R ₁-R ₆specifically in table 1.

Table 12: in compound of Formula I 12-1-91, G ₁for CH, G ₂for CH, G ₃for C-OCH ₃, R ₁-R ₆specifically in table 1.

Table 13: in compound of Formula I 13-1-91, G ₁for CH, G ₂for CH, G ₃for C-OCH (CH ₃) ₂, R ₁-R ₆specifically in table 1.

Table 14: in compound of Formula I 14-1-91, G ₁for N, G ₂for CH, G ₃for C-CO ₂c ₂h ₅, R ₁-R ₆specifically in table 1.

Table 15: in compound of Formula I 15-1-91, G ₁for C-CN, G ₂for CH, G ₃for C-Br, R ₁-R ₆specifically in table 1.

Table 16: in compound of Formula I 16-1-91, G ₁for C-NO ₂, G ₂for CH, G ₃for C-CF ₃, R ₁-R ₆specifically in table 1.

Table 17: in compound of Formula I 17-1-91, G ₁for N, G ₂for CH, G ₃for C-CONH ₂, R ₁-R ₆specifically in table 1.

Table 18: in compound of Formula I 18-1-91, G ₁for CH, G ₂for C-Cl, G ₃for CH, R ₁-R ₆specifically in table 1.

Table 19: in compound of Formula I 19-1-91, G ₁for N, G ₂for CH, G ₃for CH, R ₁-R ₆specifically in table 1.

Table 20: in compound of Formula I 20-1-91, G ₁for N, G ₂for CH, G ₃for C-CF ₃, R ₁-R ₆specifically in table 1.

Table 21: in compound of Formula I 21-1-91, G ₁for N, G ₂for CH, G ₃for C-CF ₂cl, R ₁-R ₆specifically in table 1.

Table 22: in compound of Formula I 22-1-91, G ₁for N, G ₂for CH, G ₃for C-CN, R ₁-R ₆specifically in table 1.

Table 23: in compound of Formula I 23-1-91, G ₁for N, G ₂for CH, G ₃for C-Cl, R ₁-R ₆specifically in table 1.

Table 24: in compound of Formula I 24-1-91, G ₁for N, G ₂for N, G ₃for C-Cl, R ₁-R ₆specifically in table 1.

Table 25: in compound of Formula I 25-1-91, G ₁for N, G ₂for CH, G ₃for N, R ₁-R ₆specifically in table 1.

Table 26: in compound of Formula I 26-1-91, G ₁for CH, G ₂for CH, G ₃for CCF (CF ₃) ₂, R ₁-R ₆specifically in table 1.

Table 27: in compound of Formula I 27-1-91, G ₁for CH, G ₂for CH, G ₃for r ₁-R ₆specifically in table 1.

Table 28: in compound of Formula I 28-1-91, G ₁for N, G ₂for C-Cl, G ₃for C-Cl, R ₁-R ₆specifically in table 1.

Compound of Formula I of the present invention can be prepared in accordance with the following methods, and in formula, each group definition is the same:

In formula: Z is selected from halogen atom; R ₁, R ₂, R ₃, R ₅, R ₆, G ₁, G ₂, G ₃respectively as previously mentioned; R ₄as previously mentioned, but R ₄≠ H.

According to above preparation method, intermediate II and intermediate III also react R in obtained general formula I in the basic conditions in suitable solvent ₄compound I-the A of=H;

By Compound I-A itself and Z-R ₄react in suitable solvent, R in general formula I can be obtained ₄compound I-the B of ≠ H.

React and carry out in suitable solvent, the suitable optional tetrahydrofuran (THF) freely of solvent, ethanol, methyl alcohol, acetonitrile, methylene dichloride, toluene, dimethylbenzene, benzene, DMF or methyl-sulphoxide etc.

The suitable optional potassium hydroxide freely of alkali, sodium hydroxide, sodium carbonate, salt of wormwood, sodium bicarbonate, triethylamine, pyridine, sodium hydride, potassium tert.-butoxide or sodium tert-butoxide etc.

Above-mentioned preparation method between room temperature to solvent boiling point temperature, can be generally 20-100 DEG C.

Above-mentioned preparation method's reaction times is 30 minutes to 20 hours, usual 1-10 hour.

Intermediate II can be obtained according to currently known methods by intermediate compound IV or V, and concrete synthesis can see CA2038521, WO2012035423, CN102311448 and US20100069383.

Intermediate compound IV and V can be commercial or obtained by currently known methods, and concrete synthesis can see US5206375 and US20040142953.

Intermediate III can be obtained according to currently known methods by following route, corresponding raw material has commercially available or reference literature US4895849, JP10036355, EP665225, US20070093498, WO2007046809, US5783522A, WO02083647A1, CN1927860A, OrganicSyntheses, Coll.Vol.10, p.501 (2004); Vol.75, p.61 (1998) or OrganicSyntheses, Coll.Vol.10, p.102 (2004); Vol.75, p.53 (1998) preparation.

(1) be prepared by raw material with Uteramin:

In formula, L is leavings group, is halogen, methanesulfonate ester or p-toluenesulfonic esters, (Boc) ₂o refers to tert-Butyl dicarbonate.

(2) cyano reduction method preparation:

In formula, L is leavings group, is halogen, methanesulfonate ester or p-toluenesulfonic esters.

It is active that compound of Formula I all demonstrates high desinsection (mite) to the insect (mite) in agriculture, civilian and zoo technical field.Therefore, technical scheme of the present invention relates to the purposes that compound of Formula I is used as to prepare desinsection (mite) agent in agricultural and other field.

Compound of Formula I can be used for preventing and treating following insect:

Coleoptera (Coleoptera) (beetle): bean weevil belongs to kind of (Acanthoscelidesspp.) (curculionid), acanthoscelides obtectus (Acanthoscelidesobtectus) (common pea weevil), Emerald ash borer (Agrilusplanipennis) (emerald ash borer, Agrilus planipennis), acupuncture needle Eimeria kind (Agriotesspp.) (wireworm), Anoplophora glabripenis (Anoplophoraglabripennis) (Asia psacotheahilaris), cotton boll resembles and belongs to kind of (Anthonomusspp.) (Culculionidae), Mexico's cotton boll resembles (Anthonomusgrandis) (bollworm), cocoon honeybee belongs to kind of (Aphidiusspp.), weevil belongs to kind of (Apionspp.) (curculionid), sugarcane cockchafer belongs to kind of (Apogoniaspp.) (grub), black suede cockchafer (Atacniussprctulus) (smaller velvety chafer), Atomaria linearis (Atomarialinearis) (little beet beetle (pygmymangoldbeetle), cucumber beetle belongs to kind of (Aulacophorespp.), beet resembles (Bothynoderespunctiventris) (beet tails curculionid), bean weevil belongs to kind of (Bruchusspp.) (curculionid), pea weevil (Bruchuspisorum) (pea weevil), Cacoesia belongs to kind of (Cacoesiaspp.), Callosobruchus maculatus (Callosobruchusmaculatus) (southern cowpea curculionid), pineapple bug (Carpophilushemipteras) (dried-frait beetle), beet tortoise beetle (Cassidavittata), it Bos kind (Ccrostcrnaspp.), Ccrotoma belongs to kind of (Ccrotomaspp.) (chrysomonad (chrysomcids)), beans chrysomelid (Cerotomatrifurcata) (the chrysomelid worm of beans), tortoise resembles and belongs to kind of (Ceutorhynchusspp.) (curculionid), Chinese cabbage seed tortoise resembles (Ceutorhynchusassimilis) (Chinese cabbage weevil (cabbageseedpodweevil)), turnip tortoise resembles (Ceutorhynchusnapi) (Caulis et Folium Brassicae capitatae curculionid (cabbagecurculio)), phyllotreta kind (Chaetocnemaspp.) (chrysomonad), Colaspis belongs to kind of (Colaspisspp.) (a native beetle), Conoderusscalaris, Conoderusstigmosus, Lee resembles (Conotrachelusnenuphar) (plum cone weevil), Cotinusnitidis (Green june beetle (GreenJunebeetle)), officinalis scotellaris (Criocerisasparagi) (officinalis beetle), rusty grain beetle (Cryptolestesferrugincus) (rust paddy beetle (rustygrainbeetle)), Cryptolestes pusillus (Cryptolestespusillus) (flat ostomatid), Cryptolestes turcicus Grouville (Cryptolestesturcicus) (Turkey paddy beetle (Turkishgrainbeetle)), Ctenicera belongs to kind of (Cteniceraspp.) (nematode), Curculio kind (Curculiospp.) (curculionid), round end rhinoceros cockchafer belongs to kind of (Cyclocephalaspp.) (grub), close some withe resembles (Cylindrocpturusadspersus) (Sunflower Receptacle grass curculionid (sunflowerstemweevil)), mango leaf-cutting resembles (Deporausmarginatus) (mango leaf-cutting curculionid (mangoleaf-cuttingweevil)), lader beetle stupid (Dermesteslardarius) (lader beetle is stupid), white abdomen skin stupid (Dermestesmaculates) (white abdomen skin is stupid), chrysomelid genus kind of (Diabroticaspp.) (chrysomelid), mexican bean ladybird (Epilachnavarivcstis) (Mexico beans beetle), moth stem weevil (raustinuscubae), pale collar resembles (Hylobiuspales) (pales weevil (palesweevil)), Phytonomus kind (Hyperaspp.) (curculionid), alfalfa leaf resembles (Hyperapostica) (alfalfa weevil), Hyperdoes belongs to kind of (Hyperdoesspp.) (an Argentinian stem weevil (Hyperodesweevil)), coffee cherry little stupid (Hypothenemushampei) (coffee cherry beetle), little stupid genus kind of (Ipsspp.) (sour jujube shin little stupid (engravers)) of tooth, lasioderma serricorne (Lasiodermaserricorne) (cigarette beetle), colorado potato bug (Leptinotarsadecemlineata) (Colorado potato beetle), Liogenysfuscus, Liogenyssuturalis, rice water weevil (Lissorhoptrusoryzophilus) (rice water weevil), the stupid genus of powder kind of (Lyctusspp.) (the stupid beetle of wooden stupid moth/powder (powderpostbeetles)), Maecolaspisjoliveti, Megascelis belong to kind of (Megascelisspp.), corn click beetle (Melanotuscommunis), nitidulid belongs to kind of (Meligethesspp.), rape nitidulid (Meligethesaeneus) (brevitarsis (blossombeetle)), May beetle (Melolonthamelolontha) (typical European chafer), Obereabrevis, linear cylinder longicorn (Oberealinearis), coconut palm moth rhinoceros cockchafer (Oryctesrhinoceros) (date palm beetle (datepalmbeetle)), trade saw-toothed grain beetle (Oryzaephilusmercator) (market saw-toothed grain beetle (merchantgrainbeetle)), saw-toothed grain beetle (Oryzaephilussurinamensis) (sawtooth paddy beetle (sawtoothcdgrainbcctlc)), beak weevil belongs to kind of (Otiorhynchusspp.) (curculionid), black angle scotellaris (Oulemamelanopus) (cereal leaf beetle (cerealleafbeetle)), Oulema oryzae (Oulemaoryzae), the short beak of rose resembles and belongs to kind of (Pantomorusspp.) (curculionid), food phyllobranchia cockchafer belongs to kind of (Phyllophagaspp.) (May/June chafer), Phvllophagacuyabana, striped flea beetle kind (Phyllotretaspp.) (chrysomonad), apple tiger resembles and belongs to kind of (Phynchitesspp.), Japan popillia flavosellata fairmaire (Popilliajaponica) (Japanese beetle), large space between muscles stupid (Prostephanustruncates) (large space between muscles long stupid (largergrainborer)), paddy stupid (Rhizoperthadominica) (the little moth of paddy (lessergrainborer)), root gill cockchafer belongs to kind of (Rhizotrogusspp.) (European chafer (Eurpoeanchafer)), Rhynchophorus kind (Rhynchophorusspp.) (curculionid), little stupid genus kind of (Scolytusspp.) (wooden stupid moth), Shenophorus belongs to kind of (Shenophorusspp.) (grain weevil), pea leaf resembles (Sitonalincatus) (pealeaf weevil (pcaleafweevil)), Sitophilus kind (Sitophilusspp.) (grain weevil first), grain weevil (Sitophilusgranaries) (paddy worm (granaryweevil)), rice weevil (Sitophilusoryzae) (rice weevil first (riceweevil)), medicinal material ostomatid (Stegobiumpaniceum) (Stegobium paniceum (drugstorebeetle)), Tribolium kind (Triboliumspp.) (flour beetle), red flour beetle (Triboliumcastaneum) (red flour beetle (redflourbeetle)), assorted plan paddy moistens (Triboliumconfusum) (confused flour beetle (confusedflourbeetle)), piebald skin stupid (Trogodermavariabile) (warehouse skin stupid (warehousebeetle)) and Zabrustenebioides.

Dermaptera (Dcrmaptcra) (earwig).

Neuroptera (Dictyoptera) (cockroach): Groton bug (Blattellagermanica) (Groton bug (Germancockroach)), oriental cockroach (Blattaorientalis) (Blatta seu periplaneta), Pennsylvania wood Lian (Parcoblattapennylvanica), periplaneta americana (Periplanetaamericana) (America roach consumptive disease (Americancockroach)), Australian cockroach (Periplanetaaustraloasiae) (Australian cockroach (Australiancockroach)), periplaneta brunnea (Pcriplanctabrunnca) (periplaneta brunnea (browncockroach)), smoke Perilpaneta americana (Periplanetafuliginosa) (Peroplaneta fluligginosa (smokybrowncockroach)), the green blattaria of sugarcane (Pyncoselussuninamensis) (sugarcane Lian (Surinamcockroach)) and long palpus blattaria (Supellalongipalpa) (brown band blattaria (brownbandedcockroach)).

Diptera (Diptera) (fly): Aedes kind (Aedesspp.) (mosquito), alfalfa is dived fly (Agromyzafrontella) (alfalfa dive fly (alfalfablotchleafminer)), Hippelates kind ((Agromyzaspp.) (Liriomyza), by Anastrepha kind (Anastrephaspp.) (fruit bat), Caribbean is by trypetid (Anastrephasuspensa) (Caribbean is by trypetid (Caribbeanfruitfly)), Anopheles kind (Anophelesspp.) (mosquito), Bactrocera kind (Batroceraspp.) (fruit bat), melon trypetid (Bactroceracucurbitae) (melon fly), citrus fruit fly (Bactroceradorsalis) (oriental fruit fly), little bar Anastrepha kind (Ceratitisspp.) (fruit bat), the little bar trypetid (Ceratitiscapitata) (medfly) in Mediterranean Sea, Chrysops kind (Chrysopsspp.) (deer horsefly), Callitroga's kind (Cochliomyiaspp.) (screw worm fly larva), Ying uranotaenia kind (Contariniaspp.) (Ying mosquito), Culex kind (Culexspp.) (mosquito), Ye Ying uranotaenia kind (Dasineuraspp.) (Ying mosquito), You Cai Ye Ying mosquito (Dasineurabrassicae) (Juan Xin Cai Ying mosquito), Delia kind (Deliaspp.), delia platura (Deliaplatura) (root maggot (seedcornmaggot)), Drosophila kind (Drosophilaspp.) (vinegar fly), Fannia kind (Fanniaspp.) (housefly), anthomyia canicularis (Fanniacanicularis) (Fannia canicularis (littlehousefly)), anthomyia scalaris (Fanniascalaris) (anthomyia scalaris), large horse botfly (Gasterophilusintestinalis) (horse botfly), Gracilliaperseae, Haematobia irritans (Haematobiairritans) (horn fly), Hylemyia kind (Hylemyiaspp.) (root maggot (rootmaggot)), heel fly (Hypodermalineatum) (laiu wire rope torsalo (commoncattlegrub)), Liriomyza kind (Liriomyzaspp.) (Liriomyza), wild cabbage liriomyza bryoniae (Liriomyzabrassica) (Liriomyza that crawls (serpentineleafminer)), sheep hippoboscid (Melophagusovinus) (sheepked), fly belongs to kind of (Muscaspp.) (housefly (muscidfly)), face fly (Muscaautumnalis) (face fly (facefly)), housefly (Vuscadomestica) (housefly (housefly)), Oestrus ovis (Oestrusovis) (sheep nose fly (sheepbotfly)), Europe frit fly (Oscinellafrit) (Oscinella frit), beet spring fly (Pegomyiabetae) (spinach leaf miner (beetleafminer)), wheat fly belongs to kind of (Phorbiaspp.), carrot fly (Psilarosae) (Radix Dauci Sativae rust fly (carrotrustfly)), cherry fruit bat (Rhagoletiscerasi) (cherry fruit bat (cherryfruitfly)), Rhagoletis pomonella (Rhagoletispomonella) (apple maggots (applemaggot)), wheat midge (Sitodiplosismosellana) (orange wheat flower mosquito (orangewheatblossommidge)), tatukira (stomoxyscalcitruns) (tatukira (stablefly)), the gadfly belongs to kind of (Tahanusspp.) (horse botfly) and large uranotaenia kind (Tipulaspp.) (daddy-longlegs).

Hemiptera (Hemiptera) (stinkbug): intend green stinkbug (Acrosternumhilare) (green stinkbug (greenstinkbug)), America paddy chinch bug (Blissusleucopterus) (chinch bug (chinchbug)), potato pretty fleahopper (Calocorisnorvegicus) (potato fleahopper (potatomirid)), cimex hemipterus (Cimexhemipterus) (cimex hemipterus (tropicalbedbug)), bedbug (Cimexlectularius) (bedbug (bedhug)), Daghertusfasciatus, Dichelopsfurcatus, cotton the red stinkbug of black wing (Dysdercussuturellus) (red cotton bug (cottonstainer)), Edessameditabunda, Europe Eurygasterspp (Eurygastermaura) (paddy worm (cerealbug)), Euschistusheros, brown smelly stinkbug (Euschistusservus) (brown stinkbug (brownstinkbug)), iS-One angle fleahopper (Helopeltisantonii), tea angle fleahopper (Helopeltistheivora) (teablightplantbug), stinkbug belongs to kind of (Lagynotomusspp.) (stinkbug), large Leptocorisa spp (Leptocorisaoratorius), different Leptocorisa spp (Leptocorisavaricornis), Lygus Hahn kind (Lygusspp.) (fleahopper (plantbug)), beanpod lygus bug (Lygushesperus) (westerntarnishedplantbug), the graceful powder stinkbug (Maconellicoccushirsutus) of the rose of Sharon, Neurocolpuslongirostris, Nezara viridula smaragdula Fabricius. (Nezaraviridula) (southerngreenstinkbug), Phytocoris kind (PhyLocorisspp.) (fleahopper), fleahopper (Phytocoriscalifornicus) is planted in California, Phytocorisrelativus, Piezodorusguildingi, four line fleahopper (Poecilocapsuslineatus) (fourlinedplantbug), Psallusvaccinicola, Pseudacystaperseae, Scaptocoriscastanea and Triatoma kind (Triatomaspp.) (cone nose worm (bloodsuckingconenosebug) of sucking blood/hunt stinkbug (kissingbug)).

Homoptera (Homoptera) (aphid, a red-spotted lizard, aleyrodid, leafhopper): acyrthosiphum pisim (Acrythosiphonpisum) (acyrthosiphum pisim (peaaphid)), adelgid belongs to kind of (Adelgesspp.) (adelgids), wild cabbage aleyrodid (Aleurodesproletella) (Caulis et Folium Brassicae capitatae aleyrodid), Aleurodicus dispersus (Aleurodicusdisperses), velvet aleyrodid (Aleurothrixusflccosus) (whitefly in bt cotton (woollywhitefly)), white wheel armored scale belongs to kind of (Aluacaspisspp.), Amrascabigutellabigutella, froghopper belongs to kind of (Aphrophoraspp.) (leafhopper (leafhopper)), California red scale (Aonidiellaaurantii) (the red a red-spotted lizard in California (Californiaredscale)), Aphis kind (Aphisspp.) (aphid), cotten aphid (Aphisgossypii) (cottonaphid), apple aphid (Aphispomi) (appleaphid), eggplant is without net aphid (Aulacorthitmsolani) (foxglove aphid (foxgloveaphid)), Aleyrodes kind (Bemisiaspp.) (aleyrodid), Bemisia argentifolii (Bemisiaargentifolii), sweet potato whitefly (Bemisiatabaci) (sweetpotatowhitefly), Diuraphis noxia (Brachycolusnoxius) (Russian aphid (Russianaphid)), officinalis tubule aphid (Brachycoryncliaasparagi) (officinalis aphid (asparagusaphid)), Brevenniarehi, brevicoryne brassicae (Brevicorynebrassicae) (Caulis et Folium Brassicae capitatae aphid), lecanium belongs to kind of (Ceroplastesspp.) (a red-spotted lizard), ceroplastes rubens (Ceroplastesrubens) (redwaxscale), snow armored scale belongs to kind of (Chionaspisspp.) (a red-spotted lizard), Aspidiotus belongs to kind of (Chrysomphalusspp.) (a red-spotted lizard), soft wax a red-spotted lizard belongs to kind of (Coccusspp.) (a red-spotted lizard), the pink bad aphid (Dysaphisplantaginea) (rosyappleaphid) of apple, green jassids belongs to kind of (Empoascaspp.) (leafhopper), apple aphid (Eriosomalanigerum) (woollyappleaphid), blow cotton a red-spotted lizard (Iceryapurchasi) (cottonycushionscale), mango yellow line leafhopper (Idioscopusnitidulus) (mangoleafhopper), small brown rice planthopper (Laodelphaxstriatellus) (smallerbrownplanthopper), lepidosaphes shimer kind (Lepidosaphesspp.), long tube Aphis kind (Macrosiphumspp.), root of Beijing euphorbia Macrosiphus spp (Macrosiphumeuphorbiae) (potato aphid (potatoaphid)), grain aphid (Macrosiphumgranarium) (Britain's wheat aphid (Englishgrainaphid)), rose aphid (Macrosiphumrosae) (rose aphid (roseaphid)), four line leafhopper (Macrostelesquadrilineatus) (Aster tataricus leafhopper (asterleafhopper)), Mahanarvafrimbiolata, Acyrthosiphon dirhodum (Metopolophiumdirhodum) (rose wheat aphid (rosegrainaphid)), Midislongicornis, black peach aphid (Myzuspersicae) (black peach aphid (greenpeachaphid)), rice green leafhopper belongs to kind of (Nephotettixspp.) (leafhopper), rice green leafhopper (Nephotettixcinctipes) (greenery cicada (greenleafhopper)), brown paddy plant hopper (Nilaparvatalugens) (brownplanthopper), chaff sheet armored scale (Parlatoriapergandii) (chaffscale), ebony armored scale (Parlatoriaziziphi) (ebonyscale), popcorn wing plant hopper (Peregrinusmaidis) (corndelphacid), froghopper belongs to kind of (Philaenusspp.) (spittle insects), grape phylloxera (Phylloxeravitifoliae) (grapephylloxera), Physokermes piceae (Physokermespiceae) (sprucebudscale), stern line mealybug belongs to kind of (Planococcusspp.) (mealybug), mealybug belongs to kind of (Pseudococcusspp.) (mealybug), the clean mealybug of pineapple (Pscudococcusbrcvipcs) (pincapplemcalybug), theatre armored scale (Quadraspidiotusperniciosus) (san jose scale (SanJosescale)), aphid a red-spotted lizard belongs to kind of (Rhapalosiphumspp.) (aphid), corn tree louse (Rhapalosiphummaida) (corn leaf aphids (cornleafaphid)), rhopalosiphum padi (Rhapalosiphumpadi) (oatbird-cherryaphid), pearl lecanium belongs to kind of (Saissetiaspp.) (a red-spotted lizard), olive pearl lecanium (Saissetiaoleae) (black a red-spotted lizard), green bugs (Schizaphisgraminum) (green bugs (greenbug)), grain aphid (Sitobionavenge) (Britain's wheat aphid), white backed planthopper (Sogatellafurcifera) (white-backedplanthopper), variegation Aphis kind (Therioaphisspp.) (aphid), line lecanium belongs to kind of (Toumeyellaspp.) (a red-spotted lizard), sound Aphis kind (Toxopteraspp.) (aphid), trialeurodes vaporariorum belongs to kind of (Trialeurodesspp.) (aleyrodid), Trialeurodes vaporariorum Westwood (Trialeurodesvaporariorum) (greenhouse whitefly (greenhousewhitefly)), knot wing trialeurodes vaporariorum (Trialeurodesabutiloneus) (bandedwingwhitefly), point armored scale belongs to kind of (Unaspisspp.) (a red-spotted lizard), vow sharp clam (Unaspisyanonensis) (arrow a red-spotted lizard (arrowheadscale)) and Zuliaentreriana.

Hymenoptera (Hymenoptera) (ant, wasp and honeybee): Myrmecina kind (Acromyrrmexspp.), Xinjiang cabbage sawfly (Athaliarosae), leaf ant belongs to kind of (Attaspp.) (Ieafcuttingants), black ant belongs to kind of (Camponotusspp.) (carpented ant (carpenterant)), Diprion kind (Diprionspp.) (sawfly (sawfly)), ant belongs to kind of (Formicaspp.) (ant), Argentine ant (Iridomyrmexhumilis) (Argentineant), Monomorium subspecies (Monomoriumssp.), MonomoriumMayr (Monomoriumminumum) (littleblackant), kitchen ant (Monomoriumpharaonis) (little red ant (Pharaohant)), Neodiprion kind (Neodiprionspp.) (sawfly), Pogonomyrmex kind (Pogonomyrmexspp.) (harvester ant), hornet belongs to kind of (Polistesspp.) (wasp (paperwasp)), Solenopsis kind (Solenopsisspp.) (fiery ant), odorous antenna (Tapoinomasessile) (odorous antenna (odoroushouseant)), Tetramorium kind (Tetranomoriumspp.) (Pavement Ant (pavementant)), Vespula kind (Vespulaspp.) (yellow jacket (yellowjacket)) and Xylocopa kind (Xylocopaspp.) (carpenter bee (carpenterbee)).

Isoptera (Isoptera) (termite): formosanes belongs to kind of (Coptotcrmcsspp.), bent jaw termite (Coptotermescurvignathus), France termite (Coptotermesfrenchii), Coptotermes formosanus Shtrari． (Coptotermesformosanus) (Formosansubterraneantermite), angle Cryptotermes kind (Cornitermesspp.) (proboscis termite (nasutetermite)), sand Cryptotermes kind (Cryptotermesspp.) (dry-wood termite), different Cryptotermes kind (Heterotermesspp.) (desert Soil termites (desertsubterraneantermite)), golden yellow different termite ((IIeterotermesaureus), kalotermitid belongs to kind of (Kalotermesspp.) (dry-wood termite), principal columns of a hall Cryptotermes kind (Incistitermesspp.) (dry-wood termite), Macrotermes kind (Macrotermesspp.) (cultivation termite (fungusgrowingtermite)), edge kalotermitid belongs to kind of ((Marginitermesspp.) (dry-wood termite), saw Cryptotermes kind (Microcerotermesspp.) (careless termite (harvestertermite)), the little termite of rice wheat (Microtermesobesi), former angle Cryptotermes kind (Procornitermesspp.), Reticulitermes kind (Reticulitermesspp.) (Soil termites), Reticulitermesbanyulensis, meadow reticulitermes flavipe (Reticulitermesgrassei), yellow limb reticulitermes flavipe (Reticulitermesflavipes) (east Soil termites), beautiful little Huang reticulitermes flavipe (Reticulitermeshageni), west reticulitermes flavipe (Reticulitermeshesperus) (west Soil termites), Sang Te reticulitermes flavipe (Reticulitermessantonensis), dwell northern reticulitermes flavipe (Reticulitermessperatus), U.S. black shin reticulitermes flavipe (Reticulitermestibialis), U.S. little black reticulitermes flavipe (Reticulitermesvirginicus), proboscis Reticulitermes kind (Schedorhinotermesspp.) and ancient Cryptotermes kind (Zootermopsisspp.) (rotten kalotermitid).

Lepidopteran (Lepidoptera) (moth and butterfly): Achoeajanata, Adoxophyes spp belongs to kind of (Adoxophyesspp.), adoxophyes moth (Adoxophyesorana), tiger belongs to kind of (Agrotisspp.) (cutworm) on ground, little cutworm ((Agrotisipsilon) (black cutworm), cotton leaf ripple noctuid (Alabamaargillacea) (cotton leafworm (cottonleafworm)), Amorbiacuneana, Amyelosistransitella (navelorangeworm), Anacamptodesdefectaria, sliver gelechiid (Anarsialineatella) (peachtwigborer), jute bridge night high (Anomissabulijera) (jutelooper), Anticarsia (Anticarsiagemmatalis) (velvetbeancaterpillar), fruittree leafroller (Archipsargyrospila) (fruittreeleafroller), rose leaf roller (Archipsrosana) (roseleafroller), volume moth belongs to kind of (Argyrotaeniaspp.) (tortricidmoths), tangerine Argyrotaenia spp (Argyrotaeniacitrana) (citrus leaf-roller (orangetortrix)), Autographagamma, Bonagotacranaodcs, Cnaphalocrocis medinali(rice leaf roller) (Borbocinnara) (riceleaffolder), cotton leaf lyonetid (Bucculatrixthurberiella) (cottonleafperforator), thin moth belongs to kind of (Caloptiliaspp.) (leaf miner), Capuareticulana, peach fruit moth (Carposinaniponensis) (peach fruit moth (peachfruitmoth)), straw borer spp kind (Chilospp.), Chlumetia transversa Walker (Chlumetiatransversa) (mangoshootborer), rose Choristoneura spp (Choristoneurarosaceana) (obliquebandedleafroller), Noctua kind (Chrysodeixisspp.), cnaphalocrocis medinalls guenee (Cnaphalocerusmedinalis) (meadow leaf roller (grassleafroller)), beans Pier kind (Coliasspp.), lichee litchi (Conpomorphacramerella), the wooden stupid moth (Cossuscossus) of fragrance (wooden stupid moth), Crambus Fabricius kind (Crambusspp.) (Sodwebworms), Lee's small kernel-eating insect (Cydiafunebrana) (Li Guoe (plumfruitmoth)), oriental fruit months (Cydiamolesta) (east heart-eating worm (orientalfruitmoth)), pea moth pod high (Cydianignicana) (peamoth), the stupid moth of apple (Cydiapomonella) (codling moth (codlingmoth)), Darnadiducta, Diaphania kind (Diaphaniaspp.) (stem borer (stemborer)), snout moth's larva belongs to kind of (Diatraeaspp.) (stem borer (stalkborer)), little sugarcane borer (Diatraeasaccharalis) (sugarcaneborer), Diatraea grandiosella (Diatraeagraniosella) (southwestercornborer), Earias kind (Eariasspp.) (bollworm), earias insulana (Eariasinsulata) (Egyptianbollworm), earias fabia (Eariasvit.ella) (roughnorthernbollworm), Ecdytopophaaurantianum, South America maize seedling phycitid (Elasmopalpuslignosellus) (lessercornstalkborer), shallow brown apple moth (Epiphysiaspostruttana) (lightbrownapplemoth), meal moth belongs to kind of (Ephestiaspp.) (a powder snout moth's larva), meal moth (Ephestiacautella) (almondmoth), tobacco powder sp (Ephestiaelutella) (tobacco snout moth's larva (tobbacomoth)), Mediterranean flour moth (Ephestiakuehniella) (Mediterraneanflourmoth), Epimeces belongs to kind of (Epimecesspp.), steinernema at night (Epinotiaaporema), Skipper of plantains (Erionotathrax) (bananaskipper), ligustrum fine tortricidae (Eupoeciliaambiguella) (grape berry moth (grapeberrymoth)), former cutworm (Euxoaauxiliaris) (armycutworm), Agrotis kind (Feltiaspp.) (cutworm), angle sword Noctua kind (Gortynaspp.) (stem borer), east moth fruit moth (Grapholitamolesta) (peach (apricot) sub-heart-eating worm (orientalfruitmoth)), treble cut snout moth (Hedyleptaindicata) (bean pyralid (beanleafwebber)), blue or green Eimeria kind (Helicoverpaspp.) (noctuid), bollworm (Helicoverpaarmigera) (cottonbollworm), paddy real noctuid (Helicoverpazea) (Pyrausta nubilalis (Hubern). ridge (snout moth's larva ridge worm/bollworm)), Heliothis kind (Heliothisspp.) (noctuid), Heliothis virescens (Heliothisvirescens) (tobaccobudworm), Hellula undalis (Hellulaundalis) (cabbagewebworm), Indarbela belongs to kind of (Indarbelaspp.) (a root moth), the stupid moth of tomato (Keiferialycopersicella) (tomatopinworm), the white wing of eggplant wild snout moth's larva (Leucinodesorbonalis) (eggplantfruitborer), pear leaf blister moth (Leucopteramalifoliella), thin moth belongs to kind of (Lithocollectisspp.), grape olethreutid (Lobesiabotrana) (grapefruitmoth), Loxagrotis belongs to kind of (Loxagrotisspp.) (noctuid), beans white line cutworm (Loxagrotisalbicosta) (westernbeancutworm), gypsymoth (Lymantriadispar) (gypsymoth), apple leaf miner (Lyonetiaclerkella) (apple leaf miner (appleleafminer)), oil palm bag moth (Mahasenacorbetti) (oilpalmbagworm), Malacosoma kind (Malacosomaspp.) (tentcaterpillars), lopper worm (Mamestrabrassicae) (dish march moth (cabbagearmyworm)), the wild snout moth's larva (Marucatestulalis) of beanpod (the wild snout moth's larva of beans), bag moth (Metisaplana) (bagworm), Mythimnaunipuncta (truearmyworm), Neoleucinodeselegantalis (little tomato moth (smalltomatoborer)), 3 water snout moth's larvas (Nymphuladepunctalis) (Cnaphalocrocis medinali(rice leaf roller) (ricecaseworm)), winter looper (Operophtherabrumata) (wintermoth), European corn borer (Ostrinianubilalis) (European corn borer (Europeancornborer)), Oxydiavesulia, the brown volume moth (Pandemiscerasana) of boundary (common glucose leaf roller (commoncurranttortrix)), apple brown bortrix (Pandemisheparana) (brownappletortrix), Africa Bodhidharma swallowtail butterfly (Papiliodemodocus), Pectinophora gossypiella (Pectinophoragossypiella) (pink bollworm (pinkbollworm)), boundary Noctua kind (Peridromaspp.) (cutworm), variegated cutworm (Peridromasaucia) (variegatedcutworm), coffee leafminer (Perileucopteracoffeella) (whitecoffeeleafminer), phthorimaea operculella (Phthorimaeaoperculella) (potatotubermoth), citrus leaf lyonetid (Phyllocnisitiscitrella), thin moth belongs to kind of (Phyllonorycterspp.) (leaf miner), small white (Pierisrapae) (external cabbage caterpillar (importedcabbageworm)), the first green noctuid of mat (Plathypenascabra), India paddy spot moth (Plodiainterpunctella) (Indianmealmoth), diamond-back moth (Plutellaxylostella) (diamondbackmoth), grape berry moth (Polychrosisviteana) (grapeberrymoth), tangerine fruit ermine moth (Praysendocarps), Fructus oleae europaeae ermine moth (Prsysoleae) (olivemoth), mythimna separata belongs to kind of (Pseudaletiaspp.) (noctuid), Pseudaletiaunipunctata (armyworm), soybean noctuid (Pseudoplusiaincludens) (soybeanlooper), looper (Rachiplusianu), yellow rice borer (Scirpophagaincertulas), moth stem night, high genus planted (Sesamiaspp.) (stem borer), Sesamia inferens (Sesamiainferens) (pinkricestemborer), powder stem snout moth's larva (Sesamianonagrioides), the brown slug moth of copper stain (Setoranitens), gelechiid (Sitotrogacerealella) (Angoumoisgrainmoth), pilleriana (Sparganothispilleriana), Spodoptera kind (Spodopteraspp.) (armyworm), beet armyworm (Spodopteraexigua) (beet armyworm (beetarmyworm)), noctuid (Spodoptcrafugipcrda) (armyworm in autumn (fallarmyworm)) is coveted on meadow, south spodoptera (Spodopteraoridania) (southern armyworm (southernarmyworm)), emerging Noctua kind (Synanthedonspp.) (root moth), Theclabasilides, Thermisiagemmatalis, casemaking clothes moth (Tineolabisselliella) (webbingclothesmoth), cabbage looper (Trichoplusiani) (cabbagelooper), Liriomyza brponiae (Tutsabsoluta), Yponomeuta kind (Yponomeutaspp.), the stupid moth of coffee leopard (Zeuzeracoffeae) (redbranchborer) and Zeuzerapyrina (the stupid moth of pears leopard (leopardmoth)).

Mallophaga ((Mallophaga) poultry louse (chewinglice)): sheep poultry louse (Bovicolaovis) (sheepbitinglouse), fiery menopon gallinae (Menacanthusstramineus) (chick poultry louse (chickenbodylouse)) and shaft louse (Menopongallinea) (common hen house (commonhenhouse)).

Orthoptera (Orthoptera) (grasshopper, locust and cricket): blackspot arna Zhong (Anabrussimplex) (rub a katydid (Mormoncricket)), mole cricket (Gryllotalpidae) (mole cricket (molecricket)), Asiatic migrotory locust (Locustamigratoria), grasshopper belongs to kind of (Melanoplusspp.) (grasshopper), guiding principle wing spinelet Zhong (Microcentrumretinerve) (angle wing katydid (angularwingedkatydid)), Pterophylla belongs to kind of (Pterophyllaspp.) (katydid), chistocercagregaria, fork-tail katydid (Scudderiafurcata) (fork-tail shrubbery tree Zhong (forktailedbushkatydid)) and black angle oncus locust (Valanganigricorni).

Anoplura (Phthiraptera) (sucking lice (suckinglouse)): sucking louse belongs to kind of (Haematopinusspp.) (ox louse and a pig lice), sheep jaw lice (Linognathusovillus) (sheep lice (sheeplouse)), head louse (Pediculushumanuscapitis) (body louse), pediculus humanus corporis (Pediculushumanushumanus) (body louse) and crab louse (Pthiruspubis) (crab louse (crablouse)).

Siphonaptera (Siphonaptera) (flea): ctenocephalides canis (Ctenocephalidescanis) (dogflea), ctenocephalides felis (Ctenocephalidesfelis) (catflea) and Pulex irritans (Pulexirritans) (humanflea).

Thysanoptera (thrips): cigarette brown thrip (Frankliniellafusca) (tobaccothrip), western classical architecture (Frankliniellaoccidentalis) (westernflowerthrips), Frankliniellashultzei, Williams flower thrips (Frankliniellawilliamsi) (corn thrips (cornthrip)), greenhouse thrips (IIeliothripshaemorrhaidalis) (greenhousethrip), Riphiphorothripscruentatus, hard Thrips kind (Scirtothripsspp), balloonflower root thrips (Scirtothripscirri) (citrusthrip), Scirothrips dorsalis (Scirtothripsdorsalis) (yellowteathrips), Taeniothripsrhopalantennalis and Thrips kind (Thripsspp.).

Thysanura (Thysanura) (moth (bristletail)): silverfish belongs to kind of (Lepismaspp.) (stupid worm (silverfish)) and special mess silverfish belongs to kind of (Thermobiaspp.) (a special mess fish).

Acarina (Acarina) (mite (mite) and cicada (tick)): Wu Shi honeybee shield mite (Acarapsiswoodi) (honeybee Tracheal mite (trachealmiteofhoneybee)), Tyroglyphus kind (Acarusspp.) (food mites), Acarus siro (Acarussiro) (paddy mite (grainmite)), mango bud mite (Aceriamangiferae) (mangobudmite), peronium Eriophyes kind (Aculopsspp.), Aculops lycopersici (Aculopslycopersici) (tomatorussetmite), Aculopspelekasi, tangerine peronium goitre mite (Aculuspelekassi), Si Shi stings goitre mite (Aculusschlechtendali) (apple thorn goitre mite (applerustmite)), lone star tick (Amblyommaamcricanum) (lonestartick), Boophilus kind (Boophilusspp.) (tick), avette short hairs tick (Brevipalpusobovatus) (privetmite), purplish red short hairs mite (Brevipalpusphoenicis) (redandblackflatmite), fat tick belongs to kind of (Demodexspp.) (mangemites), Dermacentor kind (Dermacentorspp.) (hard tick), America dog tick (Dermacentorvariabilis) (americandogtick), dermatophagoides pteronyssinus (Dermatophagoidespteronyssinus) (housedustmite), Eotetranychus kind (Eotetranycusspp.), Eotetranychus carpini (Eotetranychuscarpini) (yellow spider mite (yellowspidermite)), Epitrimerus kind (Epitimerusspp.), Eriophyes kind (Eriophyesspp.), hard tick belongs to kind an of (work, odesspp.) (tick), Panonychus citri belongs to kind of ((Metatetranycusspp.), notoedres cati (Notoedrescati), Oligonychus kind (Oligonychusspp.), coffee unguiculus mite (Oligonychuscoffee), ilex Oligonychus (Oligonychusilicus) (southernredmite), Panonychus citri belongs to kind of (Panonychusspp.), Jie-Li enzyme-SQ (Panonychuscirri) (orange spider (citrusredmite)), panonychus ulmi (Panonychusulmi) (European red spider (Europeanredmite)), tangerine wrinkle leaf thorn goitre (Phyllocoptrutaoleivora) (citrusrustmite), Polyphagotarsonemus latus Banks (Polyphagotarsonemunlatus) (broad mite (broadmite)), brown dog tick (Rhipicephalussanguineus) (brown dog tick (browndogtick)), root mite belongs to kind of (Rhizoglyphusspp.) (root mite (bulbmite)), itch mite (Sarcoptesscabiei) (itchmite), avocado apical cap goitre mite (Tegolophusperseaflorae), Tetranychus kind (Tetranychusspp.), T.urticae Koch (Tetranychusurticae) (2 spider mites (twospottedspidermite)) and Di Shi watt of mite (Varroadestructor) (honeybee mite).

Nematoda (nematode): Aphelenchoides kind (Aphelenchoidesspp.) (bud and leaf and pine wood nematode (budandleaf & pinewoodnematode)), thorn Turbatrix kind (Belonolaimusspp.) (stingnematodes), little loop wire Eimeria kind (Criconemellaspp.) (ringnematodes), heart worm (Dirofilariaimmitis) (dogheartworm), Ditylenchus kind (Ditylenchusspp.) (stem and bulb eelworm), sour jujube rubber-insulated wire Eimeria kind (Heteroderaspp.) (cystnematode), corn Cyst nematode (Heteroderazeae) (corncystnematode), Hirschmanniella kind (Hirschmanniellaspp.) (rootnematodes), tie Turbatrix kind (Hoplolaimusspp.) (lancenematodes), Meloidogyne kind (Meloidogynespp.) (root knot nematode), Meloidogyne incognita ((Meloidogyneincognita) (root knot nematode), Onchocerca caecutiens (Onchocercavolvulus) (hook-tailworm), Pratylenchidae belongs to kind of (PraLylenchusspp.) (rotten nematode (lesionnematode)), perforation line Eimeria kind (Radopholusspp.) (similes thorne (burrowingnematode)) and banana reniform nematode (Rotylenchusreniformis) (kidney-shapednematode).

Symphyla (comprehensive insects): kahikatea worm (Scutigerellaimmaculata).

Especially, to black peach aphid, small cabbage moth, mythimna separata, carmine spider mite, at lower doses still there is good prevention effect.

Due to the characteristic that it is positive, above-claimed cpd can be advantageously used in protecting agriculture and the important crop of horticulture, domestic animal and breeding stock, and the environment that often goes of the mankind avoids having the injury of insect, mite.

For obtaining ideal effect, the consumption of compound changes because of various factors, the formulation of the crop of such as compound used therefor, wish protection, the type of harmful organism, gradient of infection, weather condition, application method, employing.

The compound of Formula I dosage of per hectare 10 grams-5 kilograms can provide sufficient prevention effect.

Another object of the present invention also relates to by using compound of Formula I, the method for the worm mite in the environment that control agricultural and the important crop of horticulture and/or domestic animal and breeding stock and/or the mankind often go.Especially, the consumption of compound changes in per hectare 10 grams-5 kilograms.

In order to be applied to agricultural, use the composition containing one or more compound of Formula I normally useful.

Therefore, another technical scheme of the present invention also comprises a kind of insecticide acaricide composition, and containing as the compound of Formula I of active ingredient and agriculturally acceptable carrier, in composition, the weight percentage of active ingredient is 0.1-99%.

The type of service of composition can be dry powder, wettable powder, missible oil, microemulsion, paste, granule, solution, suspension agent etc.: concrete application is depended in the selection of types of compositions.

Composition is prepared in a known way, such as optional under the existence of tensio-active agent, by with solvent medium and/or solid diluent or lytic activity material.

Available solid diluent or carrier are such as: silicon-dioxide, kaolin, wilkinite, talcum, diatomite, rhombspar, calcium carbonate, magnesium oxide, chalk, clay, synthetic silicate, attapulgite, sepiolite.

Than water, available liquid diluent is such as aromatic organic solvent (mixture, chlorobenzene etc. of dimethylbenzene or alkylbenzene), paraffin (petroleum fractions), alcohols (methyl alcohol, propyl alcohol, butanols, octanol, glycerine), ester class (ethyl acetate, isobutyl acetate etc.), ketone (pimelinketone, acetone, methyl phenyl ketone, isophorone, ethyl pentyl group ketone etc.), amides (DMF, N-Methyl pyrrolidone etc.).

Available tensio-active agent is sodium, calcium, triethylamine or the triethanolamine salt of polyoxyethylene ester, sulfonated lignin etc. of alkylsulfonate, alkylaryl sulphonate, polyoxyethylene alkylphenol, sorbyl alcohol.

Composition also can be used for specific object containing special additive, and such as tackiness agent is as gum arabic, polyvinyl alcohol, polyvinylpyrrolidone etc.

In above-mentioned composition, the concentration of activeconstituents can change in relative broad range according to the preparation type of activeconstituents, its application target, envrionment conditions and employing.Usually, the concentration range of activeconstituents is 1-90%, preferred 5-60%.

If need, can add in composition can with other activeconstituentss of compound of Formula I compatibility, such as other insecticidal/acaricidal agents, sterilant, plant-growth regulator, microbiotic, weedicide, fertilizer etc.

The compound method of several formulation is exemplified below:

The preparation of suspension agent: in common prescription, active component content is 5%-35%.Take water as medium, former medicine, dispersion agent, suspending agent and antifreezing agent etc. are added in sand mill, grinds, make suspension agent.

The preparation of aqueous emulsion: former medicine, solvent and emulsifying agent are added together, makes to be dissolved into homogeneous oil phase.Water, antifreezing agent etc. are mixed, become homogeneous aqueous phase.Under high velocity agitation, aqueous phase joined oil phase or oil phase is joined aqueous phase, forming the aqueous emulsion of favorable dispersity.Aqueous emulsion active component content of the present invention is generally 5%-15%.For preparation emulsifiable concentrate, compound being soluble solution of the present invention in one or several mixed solvents, then adds emulsifying agent to strengthen the dispersion effect of compound in water.

The preparation of wettable powder: by recipe requirements, by the fully mixing such as former medicine, various tensio-active agent and solid diluent, after ultra-fine pulverizer disintegrating, namely obtains the wettable powder product of predetermined content (such as 10%-40%).For preparation is suitable for the wettable powder of sprinkling, compound of the present invention can with the pressed powder of porphyrize as clay, inorganic silicate, carbonate and wetting agent, tackiness agent and/or dispersion agent composition mixture.

The preparation of water-dispersible granules: former medicine and powdered solid diluents, wetting spreader-sticker and tackiness agent etc. are carried out co-grinding; add water after mediating again; add in the tablets press that 10 to 100 eye mesh screens are housed and carry out granulation, and then drying, screening (by screen cloth scope).Also can add in sand mill by former medicine, dispersion agent, disintegrating agent and wetting agent and solid diluent, take water as medium milling, make suspension agent, then carry out spray drying granulation, usual formulation content is 20%-30% granular product.

Embodiment

Following specific embodiment is used for further illustrating the present invention, but the present invention is only limitted to absolutely not these examples.(raw materials used have commercially available)

Synthetic example

Embodiment 1: the preparation of intermediate 4-(4-cyano group-2-fluorophenoxy) phenethylamine hydrochloride

(1) preparation of N-Boc-4-hydroxyphenethylamine

11.3g (0.1mol) 4-hydroxyphenethylamine is dissolved in 80ml tetrahydrofuran (THF), add 10.08g (0.12mol) sodium bicarbonate successively, 50ml water, 21.80g (0.1mol) tert-Butyl dicarbonate is dripped under stirring at room temperature, drip and finish, continue reaction 4-10 hour, TLC monitoring after completion of the reaction, remove solvent under reduced pressure, add (3 × 50ml) extraction into ethyl acetate, organic phase saturated aqueous common salt 50ml washs, decompression precipitation, (eluent is ethyl acetate and sherwood oil (boiling range 60-90 DEG C) to resistates column chromatography, volume ratio is 1:4) be separated to obtain white solid 17.15g, yield 81%, fusing point 48-49 DEG C.

(2) preparation of 4-(4-cyano group-2-fluorophenoxy) benzene ethylamino t-butyl formate

By 2.37g (0.01mol) N-Boc-4-hydroxyphenethylamine and 1.39g (0.01mol) 3,4-difluorophenyl adds in 50ml butanone, add 2.76g (0.02mol) salt of wormwood again, backflow is heated under stirring, react 8 hours, TLC monitoring after completion of the reaction, remove solvent under reduced pressure, add (3 × 50ml) extraction into ethyl acetate, organic phase saturated aqueous common salt 50ml washs, decompression precipitation, and (eluent is ethyl acetate and sherwood oil (boiling range 60-90 DEG C) to resistates column chromatography, volume ratio is 1:5) obtain white solid 2.85g, yield 80%.

(3) preparation of 4-(4-cyano group-2-fluorophenoxy) phenethylamine hydrochloride

3.56g (0.01mol) 4-(4-cyano group-2-fluorophenoxy) benzene ethylamino t-butyl formate is added in 50ml ethyl acetate, 15ml concentrated hydrochloric acid is dripped under stirring at room temperature, dissolution of solid, continuing stirring has a large amount of solid to separate out after 4 hours, suction filtration, filter cake 10ml ethyl acetate washs to obtain 2.81g white solid, yield 96%, fusing point 245-246 DEG C.

Embodiment 2: the preparation of intermediate 4,5-dichloro-thiophene also [2,3-d] pyrimidine

Get 2-Amino 3 cyano-4-oxygen base-4,5-dihydro-thiophene and 250ml phosphorus oxychloride (POCl ₃) in reaction flask, under room temperature, slowly drip 38ml dimethyl formamide (DMF), within about 30 minutes, dropwise.Room temperature reaction 1 hour, then be warming up to 75 DEG C of reactions 3 hours.After being down to room temperature, reaction solution is poured in trash ice, filter to obtain dark gray solid 89.1g, yield 86.9%, fusing point 160-161 DEG C.

Embodiment 3: the preparation of compound table 1-2

Get 2.05g (0.01mol) 4, 5-dichloro-thiophene also [2, 3-d] pyrimidine and 2.93g (0.01mol) 4-(4-cyano group-2-fluorophenoxy) phenethylamine hydrochloride be in 50ml ethanol, 3.03g (0.03mol) triethylamine is added under stirring at room temperature, be heated to backflow, react 5 hours, TLC monitoring after completion of the reaction, remove solvent under reduced pressure, add (3 × 50ml) extraction into ethyl acetate, organic phase saturated aqueous common salt 50ml washs, decompression precipitation, (eluent is ethyl acetate and sherwood oil (boiling range 60-90 DEG C) to resistates column chromatography, volume ratio is 1:3) obtain white solid 3.56g, yield 83.8%, fusing point 135 ~ 136 DEG C.

Nuclear magnetic data ¹h-NMR (300MHz, interior mark TMS, solvent C DCl ₃) as follows: δ (ppm): 8.48 (s, 1H), 7.49 (d, 1H), 7.38 (d, 1H), 7.32 (d, 2H), 7.05 (s, 1H), 7.04 (d, 2H), 6.92 (d, 1H), 6.52 (m, 1H), 3.91 (m, 2H), 3.02 (m, 2H).

Embodiment 4: the preparation of intermediate 2-(4-(5-5-flumethiazine-2-oxygen base) phenyl) ethamine

(1) preparation of 2-(4-(5-(trifluoromethyl) pyridine-2-oxygen base) phenyl) acetonitrile

18.15g (0.1mol) 2-chloro-5-trifluoromethylpyridine and 15.96g (0.12mol) p-hydroxybenzylcyanide are added in 200ml butanone, add 27.60g (0.2mol) salt of wormwood, backflow is heated under stirring, react 10 hours, TLC monitoring after completion of the reaction, remove solvent under reduced pressure, add 300ml extraction into ethyl acetate, organic phase uses 5% aqueous sodium hydroxide solution successively, the each 50ml washing of saturated aqueous common salt, decompression precipitation, (eluent is ethyl acetate and sherwood oil (boiling range 60-90 DEG C) to resistates column chromatography, volume ratio is 1:5) obtain white solid 22.50g, yield 81%, fusing point 48-49 DEG C.

(2) preparation of 2-(4-(5-5-flumethiazine-2-oxygen base) phenyl) ethamine

Mixture 2.78g (0.01mol) 2-(4-(5-5-flumethiazine-2-oxygen base) phenyl) acetonitrile, Raney nickel (1.0g), 10ml25% ammoniacal liquor and 50ml ethanol formed is at hydrogen atmosphere, stirred at ambient temperature reaction 3-15 hour, TLC monitoring after completion of the reaction, filtering Raney nickel, remove solvent under reduced pressure and obtain viscous liquid, white solid 2.20g is obtained after cooling, yield 78%, fusing point 82-83 DEG C.

Embodiment 5: the preparation of chloro-5, the 6-thioxenes of intermediate 4-also [2,3-d] pyrimidine

The preparation of (1) 5,6-thioxene also [2,3-d] pyrimidine-4 (3H)-one

Get 19.9g (0.1mol) 2-amino-4,5-thioxene-3-ethyl formate is in 100ml methane amide, temperature rising reflux reacts 6 hours, after completion of the reaction, reaction solution is down to room temperature, adds 100ml water in TLC monitoring, continue stirring 1 hour, filter to obtain field gray solid 15.3g, yield 85%, fusing point 274-275 DEG C.

(2) preparation of chloro-5, the 6-thioxenes of 4-also [2,3-d] pyrimidine

Get 1.8g (0.01mol) 5,6-thioxene also [2,3-d] pyrimidine-4 (3H)-one is in 10ml sulfur oxychloride, add a dimethyl formamide (DMF) again, temperature rising reflux reacts 3 hours, and TLC monitoring after completion of the reaction, removes solvent under reduced pressure and obtains dark gray solid 1.8g, yield 90.6%, fusing point 112-113 DEG C.

Embodiment 6: the preparation of compound table 20-19

Get 0.3g (1.5mmol) 4-chloro-5, 6-thioxene also [2, 3-d] pyrimidine and 0.42g (1.5mmol) 2-(4-(5-5-flumethiazine-2-oxygen base) phenyl) ethamine is in 50ml ethanol, 0.5g (5mmol) triethylamine is added under stirring at room temperature, be heated to backflow, react 5 hours, TLC monitoring after completion of the reaction, remove solvent under reduced pressure, add (3 × 50ml) extraction into ethyl acetate, organic phase saturated aqueous common salt 50ml washs, decompression precipitation, (eluent is ethyl acetate and sherwood oil (boiling range 60-90 DEG C) to resistates column chromatography, volume ratio is 1:3) obtain white solid 0.33g, yield 50%, fusing point 109 ~ 110 DEG C.

Nuclear magnetic data ¹h-NMR (300MHz, interior mark TMS, solvent C DCl ₃) as follows: δ (ppm): 8.42 (s, 1H), 8.41 (s, 1H), 7.89 (d, 1H), 7.31 (d, 2H), 7.12 (d, 2H), 7.01 (d, 1H), 5.44 (brs, 1H), 3.89 (m, 2H), 3.02 (m, 2H), 2.38 (s, 3H), 2.25 (s, 3H).

The preparation of other compounds of the present invention all can refer to above example.

The physical data of part of compounds and nuclear magnetic data ( ¹hNMR, 300MHz, interior mark TMS, solvent C DCl ₃) as follows:

Compound table 1-1: clear yellow viscous.δ(ppm):8.52(s,1H),7.50(d,1H),7.38(d,1H),7.28(d,2H),7.04(d,2H),6.94(m,1H),5.29(brs,1H),3.86(m,2H),3.00(t,2H),2.80(s,2H),2.68(s,2H),1.86(m,4H)。

Compound table 1-23: fusing point 146-147 DEG C.δ(ppm):8.40(s,1H),7.48(d,1H),7.57(d,1H),7.34(d,2H),7.04(s,1H),7.04(d,2H),6.98(d,1H),6.66(brs,1H),3.75(m,2H),2.95(t,2H),2.51(s,3H)。

Compound table 2-2: fusing point 109-110 DEG C.δ(ppm):8.48(s,1H),7.32(d,1H),7.13(d,1H),7.06(d,2H),7.04(s,1H),7.04(d,2H),6.82(d,1H),6.53(s,1H),3.86(m,2H),2.93(t,2H)。

Compound table 5-2: fusing point 104-105 DEG C.δ(ppm):8.49(s,1H),7.29(d,1H),6.98-7.09(m,4H),6.81-6.85(m,2H),6.57(s,1H),3.91(m,2H),3.02(m,2H)。

Compound table 6-2: fusing point 119-120 DEG C.δ(ppm):8.48(s,1H),7.56(d,2H),7.30(d,2H),7.26(s,1H),7.04(d,2H),7.01(d,2H),6.48(s,1H),3.91(m,2H),3.02(t,2H)。

Compound table 8-53: fusing point 181-182 DEG C.δ(ppm):8.47(s,1H),8.32(m,2H),7.22(d,2H),7.04(s,1H),6.80(d,2H),6.50(s,1H),6.53(s,1H,NH),3.89(m,2H),2.98(t,2H)。

Compound table 10-2: fusing point 84-85 DEG C.δ(ppm):8.47(s,1H),7.20(d,2H),7.13(d,2H),7.03(s,1H),6.94(d,2H),6.88(d,2H),6.52(m,1H),3.88(m,2H),2.97(t,2H),2.33(s,3H)。

Compound table 11-2: fusing point 107-108 DEG C.δ(ppm):8.47(s,1H),7.25(m,4H),7.02(s,1H),6.96(d,2H),6.90(d,2H),6.52(s,1H),3.88(m,2H),2.98(t,2H)。

Compound table 12-2: fusing point 111-112 DEG C.δ(ppm):8.47(s,1H),7.20(d,2H),7.03(s,1H),6.97(d,2H),6.95(d,2H),6.88(d,2H),6.53(m,1H),3.87(m,2H),3.81(s,3H),2.97(t,2H)。

Compound table 13-2: brown oil.δ(ppm):8.47(s,1H),7.19(d,2H),7.03(s,1H,),6.94(d,2H,Ph-2,6-H),6.92(d,2H),6.88(d,2H),6.53(m,1H),4.48(q,1H),3.87(m,2H),3.81(s,3H),2.96(t,2H),1.33(d,6H)。

Compound table 14-2: fusing point 102-103 DEG C.δ(ppm):8.82(d,1H),8.48(s,1H),8.26(d,1H),7.34(d,2H),7.14(d,2H),7.04(s,1H),6.92(d,1H),6.57(s,1H),4.38(q,2H),3.93(q,2H),3.04(t,2H),1.37(t,3H)。

Compound table 14-53: fusing point 154-155 DEG C.δ(ppm):8.63(d,1H),8.48(s,1H),8.34(d,1H),7.33(d,2H),7.12(t,2H),7.04(s,1H),6.57(s,1H),4.38(q,2H),3.93(q,2H),3.03(t,2H),1.39(t,3H)。

Compound table 15-2: fusing point 144-145 DEG C.δ(ppm):8.48(s,1H),7.75(s,1H),7.55(d,1H),7.31(d,2H),7.05(s,1H),7.03(d,2H),6.68(d,1H),6.56(m,1H),3.91(m,2H),3.02(t,2H)。

Compound table 16-2: fusing point 124-125 DEG C.δ(ppm):8.48(s,1H),7.85(s,1H),7.65(d,1H),7.31(d,2H),7.05(s,1H),7.03(d,2H),6.78(d,1H),6.56(brs,1H),3.91(m,2H),3.02(t,2H)。

Compound table 17-53: fusing point 125-126 DEG C.δ(ppm):8.48(s,1H),8.39(d,1H),8.25(d,1H),7.35(d,2H),7.14(d,2H),7.04(s,1H),3.93(q,2H),3.04(t,2H)。

Compound table 18-73: fusing point 141-142 DEG C.δ(ppm):8.49(s,1H),7.29(d,2H),6.98-7.09(m,4H),6.81-6.85(q,2H),6.57(s,1H),3.91(m,2H),3.02(t,2H)。

Compound table 19-1: fusing point 118-119 DEG C.δ(ppm):8.53(s,1H),8.43(s,1H),7.90(q,1H),7.27(q,3H),7.09(d,3H),7.01(d,1H),5.58(d,1H),3.92(q,2H),3.02(t,2H)。

Compound table 19-5: oil.δ(ppm):8.44(d,2H),7.90(d,1H),7.31(d,2H),7.12(d,2H),7.01(d,1H),5.44(s,1H),3.92(q,2H),3.04(t,2H),2.39(s,3H)。

Compound table 19-68: yellow oil.δ(ppm):8.48(s,1H),8.28(d,1H),8.28(d,1H),7.32(d,2H),7.26(s,1H),7.13(d,2H),7.03(d,1H),6.57(m,1H),3.92(m,2H),3.02(t,2H)。

Compound table 20-52: fusing point 144-145 DEG C.δ(ppm):8.53(s,1H),8.26(s,1H),7.98(d,1H),7.27(m,3H),7.12(m,3H),5.66(d,1H),3.92(q,2H),3.04(t,2H)。

Compound table 20-53: oil.δ(ppm):8.48(s,1H),8.26(d,1H),7.98(d,1H),7.35(d,2H),7.14(d,2H),7.04(s,1H),6.55(q,1H),3.93(q,2H),3.04(t,2H)。

Compound table 20-54: oil.δ(ppm):8.45(s,1H),8.25(d,1H),7.98(d,1H),7.30(t,2H),7.15(t,2H),6.78(s,1H),5.45(s,1H),3.92(q,2H),3.04(t,2H),2.38(s,3H)。

Compound table 20-56: thickness.δ(ppm):8.40(s,1H),8.25(d,1H),7.98(d,1H),7.31(d,2H),7.12(d,2H),5.28(brs,1H),3.87(m,2H),3.02(t,2H),2.77(brs,2H),2.67(brs,2H),1.85(m,4H)。

Compound table 21-53: thickness.δ(ppm):8.49(s,1H),8.27(m,1H),7.99(d,1H),7.35(d,2H),7.14(d,2H),7.04(d,1H),6.56(s,1H),3.93(m,2H),3.04(t,2H)。

Compound table 22-2: fusing point 108-109 DEG C.δ(ppm):8.46(t,2H),7.91(q,1H),7.34(d,2H),7.11(d,2H),7.02(d,2H),6.55(s,1H),3.93(q,2H),3.03(t,2H)。

Compound table 22-53: fusing point 154-155 DEG C.δ(ppm):8.48(s,1H),7.49(s,1H),7.99(s,1H),7.36(d,2H),7.13(d,2H),7.05(s,1H),6.58(s,1H),3.93(m,2H),3.04(t,2H)。

Compound table 24-2: thickness.δ(ppm):8.48(s,1H),7.47(d,1H),7.32(d,2H),7.17(d,1H),7.13(d,2H),7.03(s,1H),6.52(m,1H),3.91(m,2H),3.02(t,2H)。

Compound table 25-78: fusing point 134-135 DEG C.δ(ppm):8.48(s,1H),8.39(s,1H),7.36(d,2H),7.13(d,2H),7.05(s,1H),6.55(m,1H),3.93(m,2H),3.05(t,2H)。

Compound table 28-53: thickness.δ(ppm):8.49(s,1H),7.85(s,1H),7.26(s,1H),7.12(d,2H),7.04(s,1H),3.93(m,2H),3.04(m,2H)。

The physical data of part of compounds and nuclear magnetic data ( ¹hNMR, 300MHz, interior mark TMS, solvent DMSO) as follows:

Compound table 1-5: fusing point 116-117 DEG C.δ(ppm):8.24(s,1H),7.88(d,1H),7.57(d,1H),7.34(d,2H),7.04(s,1H),7.04(d,2H),6.98(d,1H),6.66(brs,1H),3.75(m,2H),2.95(t,2H),2.51(s,3H)。

Compound table 1-19: fusing point 171-172 DEG C.δ(ppm):8.19(s,1H),7.85(d,1H),7.57(d,1H),7.33(d,2H),7.02(d,2H),7.01(d,1H),6.61(brs,1H),3.74(m,2H),2.95(t,2H),2.50(s,6H)。

Compound table 5-53: fusing point 168-169 DEG C.δ(ppm):8.36(s,1H),8.05(s,2H),7.57(s,1H),7.23(s,2H),7.18(s,1H),6.78(d,2H),3.68(m,2H),2.89(t,2H)。

Example of formulations (each component add-on is weight percentage, is metered into after active compound folding hundred)

Embodiment 7:30% compound table 1-2 wettable powder

Above-claimed cpd table 1-2 and other components are fully mixed, after ultra-fine pulverizer disintegrating, namely obtains the wettable powder product of 30%.

Embodiment 8:40% compound table 1-2 suspension concentrates

Compound table 1-2 and other components fully mix, the suspension concentrates obtained thus, and dilute with water gained suspension agent can obtain the diluent of any desired concn.

Embodiment 9:60% compound table 20-19 water-dispersible granules

By compound table 20-19 and other component co-grindings, then add water mediate after, add in the tablets press of 10-100 eye mesh screen and carry out granulation, and then drying, screening (by screen cloth scope).

Biological activity determination example

Embodiment 10 insecticidal activity assay

Insecticidal activity assay test has been carried out to several insect with the compounds of this invention sample.The method of test is as follows:

Testing compound is diluted to required concentration with the water containing 0.1% (wt) tween 80 after dissolving with the mixed solvent of acetone/methanol (1:1).

With small cabbage moth, mythimna separata, black peach aphid and carmine spider mite for target, airbrush spray method is adopted to carry out insecticidal activity assay.

(1) to the determination of activity of small cabbage moth

Measuring method: leaf dish cabbage leaves punch tool being broken into diameter 2cm, the pressure of airbrush spraying process is that 10psi (is roughly equal to 0.7kg/cm ²), every leaf dish pros and cons spraying, spouting liquid is 0.5ml.Often process access after drying in the shade and try worm 10 2 ages, often process 3 times and repeat.Put into 25 DEG C, relative humidity 60 ~ 70% observation indoor cultivation after process, 72 hours " Invest, Then Investigate " survival borer populations, calculate mortality ratio.

As follows to the partial test result of small cabbage moth:

When liquor strength is 600ppm, more than 80%, have compound table 1-1,1-2,1-5,5-2,10-2,11-2,12-2,13-2,19-1,19-5,19-68,20-2,20-19,20-53,24-2 etc. to the lethality rate of small cabbage moth; Wherein the lethality rate of compound table 1-2,1-5,10-2,11-2,12-2,13-2,19-68,20-53,24-2 is 100%; Control compound KC1 and KC3 is 67% and 50% to the lethality rate of small cabbage moth under 600ppm.

When liquor strength is 100ppm, 11-2 is 100% to the lethality rate of small cabbage moth; 1-1,1-2,1-5,12-2 are more than 70% to the lethality rate of small cabbage moth; Control compound KC2 is 27% to the lethality rate of small cabbage moth under 100ppm.

(2) to the determination of activity of mythimna separata:

Measuring method: leaf section maize leaf being cut into long 2cm, the pressure of airbrush spraying process is that 10psi (is roughly equal to 0.7kg/cm ²), every leaf section pros and cons spraying, spouting liquid is 0.5ml.Often process access after drying in the shade and try worm 10 2 ages, often process 3 times and repeat.Put into 25 DEG C, relative humidity 60 ~ 70% observation indoor cultivation after process, 72 hours " Invest, Then Investigate " survival borer populations, calculate mortality ratio.

As follows to the partial test result of mythimna separata:

When liquor strength is 600ppm, more than 80%, have 1-1,1-2,1-5,1-19,1-23,10-2,11-2,19-5,19-68,20-2,20-53,24-2 etc. to the lethality rate of mythimna separata; Wherein the lethality rate of 1-1,1-19,11-2,20-53 is 100%.Control compound KC1, KC2 and KC4 are respectively 14%, 0% and 29% to the lethality rate of mythimna separata under 600ppm.

(3) to the determination of activity of black peach aphid:

Measuring method: cut-off footpath 6cm culture dish, covers one deck filter paper at the bottom of ware, and drips appropriate tap water moisturizing.Clip suitable size (diameter is about 3cm) from the cabbage plant cultivating black peach aphid and the long cabbage leaves having 15 ~ 30 aphids, remove the aphid of alatae and face of blade, blade back is upwards placed in culture dish.The pressure of airbrush spraying process is 10psi (being roughly equal to 0.7kg/cm2), and spouting liquid is 0.5ml, often processes 3 times and repeats.Put into 25 DEG C, relative humidity 60 ~ 70% observation indoor cultivation after process, 48 hours " Invest, Then Investigate " survival borer populations, calculate mortality ratio.

As follows to the partial test result of black peach aphid:

When liquor strength is 600ppm, more than 80%, have 1-1,1-2,1-5,1-19,1-23,5-2,6-2,10-2,11-2,12-2,13-2,14-2,14-53,18-73,19-1,19-5,19-68,20-2,20-19,20-52,20-53,20-54,21-53,22-2,24-2 etc. to the lethality rate of black peach aphid; Wherein the lethality rate of 1-1,1-2,1-5,1-19,1-23,5-2,6-2,10-2,11-2,12-2,13-2,14-2,19-1,19-5,19-68,20-2,20-19,20-53,21-53,22-2,24-2 is 100%;

When liquor strength is 100ppm, more than 80%, have 1-1,1-2,1-5,1-19,1-23,5-2,6-2,10-2,11-2,12-2,13-2,14-2,18-73,19-1,19-5,19-68,20-2,20-19,20-52,20-53,20-54,21-53,22-2,24-2 etc. to the lethality rate of black peach aphid; Wherein the lethality rate of 1-1,1-2,1-5,1-19,5-2,6-2,10-2,13-2,14-2,19-1,19-5,19-68,20-2,20-19,20-52,20-53,20-54,24-2 is 100%;

When liquor strength is 10ppm, more than 80%, have 1-1,1-2,1-5,1-19,6-2,10-2,11-2,12-2,13-2,14-2,19-1,19-5,19-68,20-2,20-19,20-52,20-54,22-2,24-2 etc. to the lethality rate of black peach aphid; Wherein the lethality rate of 1-1,6-2,10-2,14-2,19-1,19-5,19-68,24-2 is 100%.Control compound KC1, KC2 and KC3 are respectively 21%, 53% and 68% to the lethality rate of black peach aphid under 10ppm.

(4) carmine spider mite is measured:

Measuring method: get two panels true leaf Kidney bean seedling, connects carmine spider mite and becomes mite and after investigating radix, carry out whole strain process with airbrush atomizer, pressure is that 10psi (is roughly equal to 0.7kg/cm ²), spouting liquid is 0.5ml.Often process and repeat for 3 times, process is placed on standard sight room, and 72 hours " Invest, Then Investigate " survival mite numbers, calculate mortality ratio.

As follows to the partial test result of carmine spider mite:

When liquor strength is 600ppm, more than 80%, have 1-1,1-2,1-5,1-23,5-2,5-53,6-2,10-2,11-2,12-2,13-2,14-2,19-1,19-5,19-68,20-2,20-19,20-53,20-54,20-56,21-53,22-2,24-2 etc. to the lethality rate of carmine spider mite; Wherein the lethality rate of 1-1,1-2,1-5,1-23,5-2,6-2,10-2,11-2,12-2,13-2,19-1,19-5,19-68,20-2,20-19,20-53,21-53,22-2,24-2 is 100%; Control compound KC2 is 76% to the lethality rate of carmine spider mite under 600ppm.

When liquor strength is 100ppm, more than 80%, have 1-2,5-2,6-2,10-2,11-2,12-2,13-2,19-1,19-5,19-68,20-2,20-19,20-54,22-2,24-2 etc. to the lethality rate of carmine spider mite; Wherein the lethality rate of 1-2,5-2,6-2,10-2,11-2,19-1,19-5,20-19,20-54 is 100%;

When liquor strength is 10ppm, wherein 1-2,6-2,13-2,19-1,19-5,20-19,20-54 etc. are more than 90% to the lethality rate of carmine spider mite.Control compound KC1, KC3 and KC4 are 42%, 35% and 17% to the lethality rate of carmine spider mite under 10ppm.

Claims

1. there is a substituted thienopyrimidine-4 aminated compounds for pesticide and miticide actility, it is characterized in that: compound structure is as shown in general formula I:

In formula:

R ₁, R ₂be selected from hydrogen, halogen, cyano group, nitro, C respectively ₁-C ₁₂alkyl, halo C ₁-C ₁₂alkyl or R ₁and R ₂carbocyclic ring or the heterocycle of saturated or unsaturated 3-6 unit is formed with the C be attached thereto;

Without to replace or optional by halogen, C on described carbocyclic ring or heterocycle ₁-C ₁₂alkyl, halo C ₁-C ₁₂alkyl, C ₁-C ₁₂alkoxyl group or halo C ₁-C ₁₂alkoxyl group replaces;

G ₁be selected from CR ₇or N; G ₂be selected from CR ₈or N; G ₃be selected from CR ₉or N; Wherein, G ₁, G ₂, G ₃be asynchronously N;

Or the salt of compound of Formula I.

2., according to the substituted thienopyrimidine-4 aminated compounds with pesticide and miticide actility according to claim 1, it is characterized in that: in general formula I,

R ₁, R ₂be selected from hydrogen, halogen, cyano group, nitro, C respectively ₁-C ₈alkyl, halo C ₁-C ₈alkyl or R ₁and R ₂carbocyclic ring or the heterocycle of saturated or unsaturated 3-6 unit is formed with the C be attached thereto;

Without to replace or optional by halogen, C on described carbocyclic ring or heterocycle ₁-C ₈alkyl, halo C ₁-C ₈alkyl, C ₁-C ₈alkoxyl group or halo C ₁-C ₈alkoxyl group replaces;

R ₄be selected from hydrogen, C ₁-C ₈alkyl or halo C ₁-C ₈alkyl;

Or the salt of compound of Formula I.

3., according to the substituted thienopyrimidine-4 aminated compounds with pesticide and miticide actility according to claim 2, it is characterized in that, in general formula I,

R ₁, R ₂be selected from hydrogen, halogen, cyano group, nitro, C respectively ₁-C ₄alkyl, halo C ₁-C ₄alkyl or R ₁and R ₂carbocyclic ring or the heterocycle of saturated or unsaturated 3-6 unit is formed with the C be attached thereto;

Without to replace or optional by halogen, C on described carbocyclic ring or heterocycle ₁-C ₄alkyl, halo C ₁-C ₄alkyl, C ₁-C ₄alkoxyl group or halo C ₁-C ₄alkoxyl group replaces;

R ₄be selected from hydrogen, C ₁-C ₄alkyl or halo C ₁-C ₄alkyl;

Or the salt of compound of Formula I.

4., according to the substituted thienopyrimidine-4 aminated compounds with pesticide and miticide actility according to claim 3, it is characterized in that, in general formula I:

R ₁, R ₂be selected from hydrogen, halogen, C respectively ₁-C ₄alkyl or R ₁and R ₂saturated 3-6 unit carbocyclic ring is formed with the C be attached thereto;

R ₃be selected from hydrogen;

R ₄be selected from hydrogen or C ₁-C ₄alkyl;

5., according to the substituted thienopyrimidine-4 aminated compounds with pesticide and miticide actility according to claim 4, its feature exists

In, in general formula I:

R ₁be selected from hydrogen, chlorine or methyl;

R ₂be selected from hydrogen or methyl;

Or R ₁and R ₂saturated 6 yuan of carbocyclic rings are formed with the C be attached thereto;

R ₃, R ₄be selected from hydrogen respectively;

R ₈be selected from hydrogen, chlorine or methoxyl group;

6. the substituted thienopyrimidine-4 aminated compounds with pesticide and miticide actility according to claim 5, is characterized in that: in general formula compound I

R ₁and R ₂when forming saturated 6 yuan of carbocyclic rings with the C be attached thereto,

R ₃, R ₄be selected from hydrogen respectively;

R ₈be selected from hydrogen, chlorine or methoxyl group;

Or, R ₁and R ₂when not becoming ring with the C that is attached thereto,

R ₁be selected from hydrogen, chlorine or methyl;

R ₂be selected from hydrogen or methyl;

R ₃, R ₄be selected from hydrogen respectively;

R ₈be selected from hydrogen, chlorine or methoxyl group;

7. the substituted thienopyrimidine-4 aminated compounds with pesticide and miticide actility according to claim 6, is characterized in that: in general formula compound I,

R ₁be selected from hydrogen, chlorine or methyl;

R ₂be selected from hydrogen or methyl;

R ₃, R ₄be selected from hydrogen respectively;

R ₅be selected from hydrogen, fluorine or chlorine;

R ₆be selected from hydrogen;

R ₇be selected from hydrogen, fluorine or chlorine;

R ₈be selected from hydrogen;

8. a compound of Formula I according to claim 1 or its salt are used as the purposes preparing Insecticidal and acaricidal agent medicine in agricultural, forestry or health field.

9. desinsection, a miticide composition, is characterized in that: the active ingredient of desinsection, miticide composition is the compound of described formula I, and in composition, the weight percentage of active ingredient is 0.1-99%.