CN107417682A

CN107417682A - A kind of substituted benzo isothiazole compound and purposes

Info

Publication number: CN107417682A
Application number: CN201710815422.8A
Authority: CN
Inventors: 许辉; 唐剑峰; 迟会伟; 刘莹; 乔思佳; 吴建挺; 韩君
Original assignee: SHANDONG UNITED PESTICIDE INDUSTRY Co Ltd
Current assignee: SHANDONG UNITED PESTICIDE INDUSTRY Co Ltd
Priority date: 2017-09-12
Filing date: 2017-09-12
Publication date: 2017-12-01
Also published as: CN109485644A; CN109485644B

Abstract

A kind of substituted benzo isothiazole compound, wherein R₁For cyano group, hydroxyl, C₁‑C₄Alkyl, cyclopropyl, cyano methyl, methoxyl group, ethyoxyl, acetyl group, trifluoroacetyl group, C₁‑C₄Alkoxy carbonyl, methyl sulphonyl or ethylsulfonyl；R₂It is independently selected from hydrogen, halogen, cyano group, methyl, methoxyl group, trifluoromethyl, trifluoromethoxy or difluoro-methoxy；N is 1,2,3 or 4；M is 1 or 2；J is thiazole, isothiazole or the pyridine of substitution, the compound of the present invention has excellent activity at low concentrations, good plant tolerance and environmental safety, can suppress or destroy various plants or soil in cure the disease fungi and the bacterium that occur, and various insects and acarid can be killed, expands sterilization and the insecticidal spectrum of compound；The raw material economics that the preparation method of the substituted benzo isothiazole compound of the present invention uses is easy to get, and preparation method yield is high, and synthesis technique cost is low, has good bactericidal activity and pesticide and miticide actility.

Description

A kind of substituted benzo isothiazole compound and purposes

Technical field

The present invention relates to technical field of pesticide, is specifically a kind of substituted benzo isothiazole compound and and purposes.

Background technology

It is inadequate to plant residue processing in production with the popularization of straw-returning and no-tillage technology in agricultural production, a lot Pathogen is survived the winter the more summer by plant, causes to have remained substantial amounts of phytopathogen in soil.In suitably growth bar Under part, pathogen can mushroom out in soil, and infect plant, growing to bring and have a strong impact on to plant.

In addition, preventing and treating pest and disease damage is easiest to generate the problem that resistance, in order to prevent the generation of resistance, can develop new Agricultural chemicals is compounded using existing agricultural chemicals, but compounded using existing agricultural chemicals it is not notable come delaying drug resistance effect, Need to increase dosage so that medicament residue is big, pollutes environment and bears, the agricultural chemicals medicine of benzo isothiazole compound One of to imitate, dosage is small, thus be the research direction of current novel pesticide.

Patent WO2010054926 discloses the benzo isothiazole compound and particular compound shown in below formula CK1, the application as agricultural insecticide.Benzo isothiazole compound formula CK1 is as follows：

Patent JP2010260811 discloses following particular compound CK2, as the application of disinfectant use in agriculture, CK2 knot Structure formula is as follows：

The content of the invention

To solve the above problems, it is an object of the invention to provide a kind of substituted benzo isothiazole compound and purposes.

The present invention to achieve the above object, is achieved through the following technical solutions：

A kind of substituted benzo isothiazole compound, the general structure of substituted benzo isothiazole compound is (I) It is shown：

Wherein, R₁For cyano group, hydroxyl, C₁-C₄Alkyl, C₁-C₄Haloalkyl, C₃-C₆Cycloalkyl, C₃-C₄Alkenyl, cyano group first Base, cyano ethyl, methoxyl group, ethyoxyl, acetyl group, trifluoroacetyl group, tribromo-acetyl base, C₁-C₄Alkoxy carbonyl, C₁-C₄Halogen For alkoxy carbonyl, trichloro-methylthio, trifluoromethyl sulphinyl base, methyl sulphonyl or ethylsulfonyl；

R₂It is independently selected from hydrogen, halogen, cyano group, methyl, methoxyl group, trifluoromethyl, trifluoromethoxy or difluoro first Epoxide；N is 1,2,3 or 4；M is 1 or 2；

J be substitution thiazole, isothiazole or pyridine, building stone J-1, J-2, J-3 or J-4；

The J-1, J-2, J-3 or J-4 structural formula is respectively：

Wherein W, X, Y and Z are each independently N or CR₃, and in J-3 and J-4, one of W, X, Y or Z are N；

R₃For hydrogen, halogen, cyano group, C₁-C₄Alkyl, trifluoromethyl, difluoromethyl, methoxyl group, ethyoxyl, trifluoromethoxy, Difluoro-methoxy, OCH₂CF₃Or OCHFCHF₂；

Or the salt of compound shown in logical formula (I).

A kind of preferable substituted benzo isothiazole compound, R₁For cyano group, hydroxyl, C₁-C₄Alkyl, cyclopropyl, cyano group Methyl, methoxyl group, ethyoxyl, acetyl group, trifluoroacetyl group, C₁-C₄Alkoxy carbonyl, methyl sulphonyl or ethylsulfonyl.

A kind of preferable substituted benzo isothiazole compound, leads in formula (I), m 1；

Compound shown in logical formula (I) and hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methanesulfonic acid, to first The salt that benzene sulfonic acid, benzoic acid, phthalic acid, maleic acid, fumaric acid, sorbic acid, malic acid or citric acid are formed.

A kind of preferable substituted benzo isothiazole compound, R₁For cyano group, hydroxyl, C₁-C₄Alkyl, cyclopropyl, cyano group Methyl, methoxyl group, ethyoxyl, acetyl group, trifluoroacetyl group, C₁-C₄Alkoxy carbonyl；R₂Be independently selected from hydrogen, halogen, Cyano group, methyl, methoxyl group, trifluoromethyl, trifluoromethoxy or difluoro-methoxy；R₃For hydrogen, halogen, cyano group, methyl, ethyl, Trifluoromethyl, difluoromethyl, methoxyl group, trifluoromethoxy or difluoro-methoxy.

A kind of preferable substituted benzo isothiazole compound, J are thiazole, isothiazole or the pyridine of substitution, the J- 1, J-2, J-3 or J-4 structural formula is respectively：

In J-1 and J-2, one of X, Y or Z are N；In J-3 and J-4, one of W, X, Y or Z are N.

A kind of further preferred substituted benzo isothiazole compound, J are the thiazole or pyridine of substitution, building stone For J-1, J-2, J-3 or J-4；

The J-1, J-2, J-3 or J-4 structural formula is respectively：

In J-1, one of Y or Z are N；In J-3 and J-4, one of W, X, Y or Z are N.

A kind of preferable substituted benzo isothiazole compound, leads in formula (I), and J is the chloro- 5- bases thiazoles of 2-, 3,4- bis- The chloro- chloro- 5- yl pyridines of 5- bases isothiazole or 2-；R₃For hydrogen or chlorine.

A kind of preferable substituted benzo isothiazole compound, leads in formula (I), R₁For cyano group, methyl, ethyl, propyl group, Isopropyl, normal-butyl, isobutyl group, cyclopropyl, cyano methyl, methoxyl group； R₂For hydrogen；N is 4.

A kind of preferable substituted benzo isothiazole compound, J are the chloro- 5- bases thiazoles of 2-, R₁For methyl, R₂For hydrogen, n =4, m=1.

Present invention additionally comprises purposes of the logical formula (I) compound or its salt in agricultural or other field, sterilized as preparing Agent, insecticidal/acaricidal agent medicine.

Present invention additionally comprises a kind of composition, containing logical formula (I) compound or its salt as active component；Wherein, composition The weight percentage of middle active component is 0.1-99%.

Present invention additionally comprises purposes of the composition in agricultural or other field, for anti-pathogen, insect evil mite.

The present invention has advantages below compared with prior art：

The compound of the present invention is to introduce R in the structure of benzo isothiazole compound₁N(CH₂)_mJ structures, the chemical combination The specific structure of thing is inhibited to most of germ, insect, nematode and acarid；And the structure has at low concentrations Excellent activity, good plant tolerance and environmental safety, can suppress or destroy various plants or soil in occur Cure the disease fungi and bacterium, and various insects and acarid can be killed, expand sterilization and the insecticidal spectrum of compound, specifically：

The compound of the present invention is inhibited to a variety of fungal diseases in plant, to Pyricularia oryzae, soybean downy mildew Germ, white rust of colza bacterium, anthracnose of sorghum bacterium, puccinia striiformis, rape Powdery Mildew, phytophthora infestans etc. are a variety of The different types of germ of crop is respectively provided with inhibitory action, and the inhibiting rate of harmful levels of pathogens is existed under 100ppm dosage More than 90%, 0.1ppm dosage lower part compound inhibiting rate still more than 20%, fungistatic effect beyond it is existing often Medicine, such as Isoprothiolane, Bravo, Fluoxastrobin, thiram, Tebuconazole etc., have a good plant tolerance, and The more existing medicine of residual in plant substantially reduces, and has good environmental safety, compound of the invention is in plant A variety of insect pests have insecticidal action, to rice water weevil, rice leafhopper, grain aphid, bollworm, colorado potato bug, pea weevil etc. no Insect pest in the various crop of same type is respectively provided with suppression insecticidal action, and the suppression under 100ppm dosage to harmful levels of pathogens Rate processed more than 90%, 0.1ppm dosage lower part compound inhibiting rate still more than 20%, fungistatic effect beyond Existing conventional medicine, such as chlopyrifos, Bassa, imidacloprid, gamma cyhalothrin, decis, Fluoxastrobin, desinsection model Enclose extensively and dosage is few, the residual in crops is low, has good environmental safety；

The present invention compound there is preferable inhibition to a variety of acarids, as Mite, rice Schizotetranychus, The acarids such as Jie-Li enzyme-SQ under 100ppm dosage to the inhibiting rate of harmful levels of pathogens more than 90%, in 0.1ppm dosage bottom Break up the inhibiting rate of compound still more than 20%, and existing miticide pyridaben is in 0.1ppm dosage lower part compound Inhibiting rate below 10；

The compound of the present invention has good inhibitory action to a variety of nematodes, such as to banana reniform nematode, rotten nematode, jade The rice nematode such as SCN under 100ppm dosage to the inhibiting rate of harmful levels of pathogens more than 90%, in 0.1ppm dosage The inhibiting rate of lower part compound is still more than 20%, and such as agent of carbofuran, legendary god of farming's pellet in 0.1ppm of existing nematicide The inhibiting rate of lower part compound is measured below 10；

The compound of the present invention due to having good sterilization, desinsection, mite killing and nematocidal effect simultaneously, therefore in agricultural An a kind of medicine is only needed in production can have the function that while desinsection, sterilization and mite killing, and dosage is small, environmentally safe, and not Resistance is easily produced, disclosure satisfy that the demand of existing agricultural chemicals.

Embodiment

It is an object of the invention to provide a kind of substituted benzo isothiazole compound and its production and use.It is logical Cross following technical scheme realization：

The halogen of the present invention：Refer to fluorine, chlorine, bromine or iodine.Alkyl：Refer to straight or branched alkyl.Cycloalkyl：Containing three or more The cyclic alkane of carbon atom, such as cyclopropyl, cyclobutyl, cyclopenta etc..Haloalkyl：Straight or branched alkyl, in these alkane Hydrogen moiety on base is all substituted by halogen atom.Alkoxy carbonyl：Alkoxy is connected in structure through carbonyl, such as CH₃OCO-, CH₃CH₂OCO-.Halo alkoxy carbonyl：Hydrogen atom on the alkyl of alkoxy carbonyl can be partly or entirely former by halogen Son is substituted, such as ClCH₂CH₂OCO-。

Table 1 lists compound of the part of compounds structural formula of the present invention as shown in formula (I),

The compound list of table 1

Note：In the compound list of table 1,1~No. 560 compound m=1,561~No. 655 compound m=2；1~ No. 370 compound (R₂) n is H, 371~No. 465 compound (R₂) n is 1-F, 466~No. 560 compound (R₂) n is 1-Cl, 561~No. 655 compound (R₂) n is H.

The synthetic route of the preparation method of compound of Formula I of the present invention is：

The preparation method comprises the following steps：

1. willIt is dissolved in the ethanol water that mass fraction is 50%, is cooled to 0 DEG C, is then added dropwise theretoControl temperature that stirring reaction 1 hour, Ran Housheng at 0~5 DEG C is added dropwise at 0~5 DEG C during dropwise addition Temperature is evaporated under reduced pressure concentration to 20~30 DEG C of stirring reactions 2~3 hours, residue is added to the water stir after, use ethyl acetate Extraction 3 times, merge organic phase, organic phase is washed with saturated common salt, is then added anhydrous magnesium sulfate and is dried, filtering, is concentrated under reduced pressure ObtainWhereinWithMol ratio be 2~5：1；

2. willBack flow reaction 10~12 hours in dioxane are sequentially added with chlorination reagent, are subtracted Pressure uses toluene crystallization after dioxane is distilled off, and filters, is obtained after dryingWhereinMol ratio with chlorination reagent is 1：2~5；The chlorination reagent is SOCl₂、POCl₃Or PCl₅；

3. by step 1. gainedStep 2. gainedSequentially added with acid binding agent In solvent, back flow reaction 8~10 hours, filter, filter cake organic solvent washing, merging filtrate, depressurize after being cooled to room temperature Organic solvent is distilled off, water is added into residue, is then extracted with ethyl acetate 3 times, merges organic phase, uses saturated common salt Washing, then add anhydrous magnesium sulfate and dry, filtering, be concentrated under reduced pressure to give

WhereinMol ratio with acid binding agent is 1~3：1：1~5；

The acid binding agent is triethylamine, pyridine, potassium carbonate or sodium hydride；

R₂It is independently selected from hydrogen, halogen, cyano group, methyl, methoxyl group, trifluoromethyl, trifluoromethoxy or difluoro first Epoxide；N is 1,2,3 or 4；M is 1 or 2；Hal is chlorine or bromine；

The J-1, J-2, J-3 or J-4 structural formula is respectively：

Wherein Hal is halogen, preferably chlorine or bromine, and optimal is chlorine.

The logical formula (I) compound of the present invention can also take following preparation methods to obtain, and (in addition to especially indicating, each group is determined Justice is the same as those described above)：

Chloro- benzo-the isothiazole 1 of 3- shown in formula (II), 1- dioxide exist with the secondary amine shown in formula (III-1) in alkali Lower reaction obtains compound shown in formula (I).

Or the chloro- benzo-isothiazole 1 of 3- shown in formula (II), 1- dioxide are deposited with the secondary amine shown in formula (III-2) in alkali Obtain compound (I-1) in lower reaction, then with chloride R₁Cl reacts to obtain compound shown in formula (I) in the presence of a base.

In formula：Hal is halogen, preferably chlorine or bromine, most preferably chlorine.

Triethylamine, pyridine, potassium carbonate or sodium hydride etc. can be selected in alkali.

Solvent may be selected from toluene, 1,2- dichloroethanes, acetonitrile or dioxane equal solvent.Reaction temperature is 25~120 ℃.Reaction can refer to Duphar EP33984, BASF WO07113119 or C.W.Whitehead, Journal of Organic Chemistry, 25,413-416,1960 or Syngenta WO2010054926 similar approach are carried out.

Chloro- benzo-the isothiazole 1 of 3- shown in formula (II), 1- dioxide can be prepared as follows：Formula (IV) institute The benzoic sulfimide shown and chlorination reagent such as SOCl₂、POCl₃Or PCl₅Reaction, 80~120 DEG C of reaction temperature.Reaction can With reference to H.B.Rode, Pharmazie, 60 (10), 723-731,2005 methods are carried out.

Benzoic sulfimide part shown in formula (IV) is commercially available, without it is commercially available when can be prepared by known method：By formula (V) 2- chlorine sulphonyl-benzoic ether shown in reacts with ammoniacal liquor, such as Desai, Ranjit C, Journal of Organic Chemistry (1994), 59 (23), 7161-7163 or Naoyuki Masuda, Bioorganic＆Medicinal Chemistry 13 (2005) 949-961 description.

2- chlorine sulphonyl-benzoic ether shown in formula (V) can refer to M.L.Trudell et al. Journal of Heterocyclic Chemistry, 2004,41,435-438 preparations：As the corresponding ortho-aminobenzoic acid first shown in formula (VI) It is prepared by ester diazotising, chlorosulfonylation.

Methyl anthranilate part shown in formula (VI) is commercially available, without it is commercially available when can be according to J.F.W.Keana etc. Bioorganic＆Medicinal Chemistry 11 (2003) 1769-1780 or F.H.Jung, J.Med.Chem.2006, It is prepared by the J.Med.Chem.2006,49,6371-6390 such as 49,955-970 or M.H.Rabinowitz methods describeds.

Benzoic sulfimide shown in some formulas (IV) can pass through metal catalyzed coupling reaction such as Stille or Heck Deng or Ullmann etherification reaction preparations are carried out by phenol and halide.These reactions can be with the standardization program phase described in document Similarly carry out, such as reference book " the Metalcatalyzed Cross Coupling Reactions " second editions, " organic name Reaction and mechanism " 2003 editions etc..

In formula：Hal is halogen, preferably chlorine or bromine.

Secondary amine shown in formula (III-1) can be reacted as the halide shown in the primary amine shown in formula (VII) and formula (VIII) to be made It is standby.Solvent may be selected from dichloromethane, butanone, acetonitrile or tetrahydrofuran polar solvent or dioxane equal solvent.Used in reaction Acid binding agent is triethylamine, pyridine, potassium carbonate or sodium hydride etc..Reaction temperature is 20~80 DEG C.

In formula：Hal is halogen, preferably iodine or bromine.Other each groups are defined as above.

Secondary amine preparation method shown in formula (III-2) is same as above, and halide that can be as shown in ammoniacal liquor with formula (VIII) is anti- It should prepare.

Primary amine shown in formula (VII) is commercially available, without it is commercially available when corresponding substituent can be passed through according to the substituent structure of definition Nitro compound, acid amides, nitrile reduction, the ammonification reduction of carbonyls, ammonia or amine hydrocarbyl reaction, the acylation of ammonia or sulphur Acylated etc. to be made, these reactions can similarly be carried out with the standardization program described in document.In reference book, " organic compound closes Into handbook " 2011 editions etc. can find many examples.

Halide moieties shown in formula (VIII) are commercially available, without it is commercially available when the formula of corresponding substituent can be passed through according to definition (Ⅸ) compound is in halide reagent such as NBS, NCS, Br₂、Cl₂Benzylation reaction is carried out Deng in the presence of to prepare.Shown in formula (VIII) Halide can also be by formula (Ⅹ) compound of corresponding substituent in chlorination reagent such as SOCl₂、POCl₃Chlorine is carried out Deng in the presence of Change reaction to prepare.

In formula：Hal is halogen, preferably chlorine or bromine.Other each groups are defined as above.

Compound part shown in formula (Ⅸ), (Ⅹ) is on sale.Without it is commercially available when document can be passed through according to the substituent structure of definition Described in standardization program analogously carry out, as reference book " heterocyclic chemistry " (fourth edition), " heterocyclic chemistry-structure, reaction, Synthesis and application " (second edition), " research and development of new heterocyclic pesticide and synthetic method " 2004, " organic name reaction and machine Reason " 2003 editions etc..Illustrated by taking substituted thiazole, isothiazole, thiophene, thiadiazoles as an example：

When J is the thiazole ring of substitution, the compound shown in some formulas (Ⅸ) can be synthesized by reaction such as Hantzsc Method is reacted by α-halogenatedketone and the reaction of substitution thioamides or Techrrnic synthetic methods by α-thio cyanogen ketone in the presence of halogen acids The methods of prepare, these reactions can similarly be carried out with the standardization program described in document, such as following thiazole rings preparation.

In formula：X is halogen, preferably chlorine or bromine.Other each groups are defined as above.

When J is the isothiazole ring of substitution, the compound shown in some formulas (Ⅸ) can be closed by reaction such as Hantzsc Prepared into method by the methods of iodine or hydrogen peroxide oxidation β-imino group thioketones or β-chloroacrolein and ammonium thiocyanate cyclizative condensation, this A little reactions can similarly be carried out with the standardization program described in document, such as the preparation of following isothiazole rings.

When J is the thiphene ring of substitution, compound shown in some formulas (Ⅸ) can be by anti-according to substituent difference Should as Pall synthetic methods by after the vulcanization of Isosorbide-5-Nitrae-dicarbonyl compound again cyclodehydration or Fiesselmann synthetic methods by β-chloropropene Aldehyde is reacted with thiol reactant or Gewald synthetic methods by alpha-methylene carbonyls and cyan-acetic ester or Hinsberg conjunctions It is prepared by the methods of being reacted into method by 1,2- dicarbonyl compounds with 3- thias glutarate, these reaction can with described in document Standardization program similarly carry out, illustrated so that Pall reactions synthesize following thiphene rings as an example.

When J is the Thiadiazole of substitution, the compound shown in some formulas (Ⅸ) can be closed by reaction such as Hurd-Mori Prepared into method by the Tosylhydrazone of ketone under thionyl chloride effect through cyclic condensation, or by the hydrazides of 1,2- bis- and P₂S₅Reaction is closed Into these reactions can similarly be carried out with the standardization program described in document, and equally to synthesize following 1,2,3- thiadiazoles are Example illustrates.

When J is the pyridine ring of substitution, there are a variety of synthetic methods, such as by 1,5- dicarbonyl compounds and ammonia synthesis, or by Hantzsch methods are prepared by ketenes or nitrile and the reaction of 1,3- dicarbonyl compound, or with Guareschi methods by cyanoacetamide system Standby, these reactions can similarly be carried out with the standardization program described in document.

, can be for example in single step reaction with according to this hair according to the selection for the reaction condition and raw material being adapted in the case of each Bright another substituent only replaces a substituent, or can be replaced in same reaction step with according to other substituents of the present invention Change multiple substituents.

If each compound can not obtain via above-mentioned route, they can be by deriving other compounds (I) or passing through The synthetic route is routinely changed and prepared.

Reactant mixture is post-processed in a usual manner, such as mutually and properly passes through color by mixing, separating with water Spectrometry is for example in aluminum oxide or purified on silica crude product.

Present invention additionally comprises the salt of logical formula (I) compound, and it can be prepared by known method.Such as by suitable Acid treatment obtain the acid-addition salts of (I) compound.Its preparation method is as follows：By logical formula (I) compound and acid such as hydrochloric acid, sulphur Acid, phosphoric acid, acetic acid, trifluoroacetic acid, malic acid or citric acid etc. react in water, ether or toluene equal solvent, can be very convenient Ground obtains the salt of logical formula (I) compound, and preparation method is as follows by taking hydrochloric acid as an example：

In formula, each group is as defined above.Reaction solvent used can be water equal solvent.20~90 DEG C of reaction temperature.

Method made above can obtain the isomer mixture of logical formula (I) compound, as that need to obtain pure isomer, can adopt With conventional method as crystallization or chromatography are separated.

Logical formula (I) compound shows excellent activity to a variety of germs in agricultural or other field, to insect evil mite Also show that preferable activity.Therefore, technical scheme also includes logical formula (I) compound in agricultural or other field As the purposes for preparing bactericide, insecticidal/acaricidal agent.

The example of disease referenced below is only used for illustrating the present invention, but never limits the present invention.

Compound of Formula I can be used for preventing and treating following disease：Oomycetes diseases, such as downy mildew (cucumber downy mildew, rape downy mildew Disease, downy mildew, beet downy mildew, downy mildew of sugarcane, tobacco downy mildew, pea downy mildew, sponge gourd downy mildew, wax gourd downy mildew Disease, muskmelon downy mildew, cabbage downy mildew, downy mildew of spinach, radish downy mildew, downy mildew of garpe, onion mildew), white rust (white rust of colza, cabbage white blister), samping off (rape samping off, Tobacco seedling diseases, tomato samping off, capsicum samping off, Eggplant samping off, cucumber samping off, cotton seedling samping off), pythium rot (capsicum pythium rot, sponge gourd pythium rot, wax gourd pythium rot), epidemic disease Disease is (broad bean epidemic disease, Cucumber Blight, pumpkin epidemic disease, wax gourd epidemic disease, watermelon epidemic disease, muskmelon blight, capsicum epidemic disease, leek epidemic disease, big Garlic epidemic disease, Cotton blight), late blight (late blight of potato, tomato late blight) etc.；Fungi Imperfecti disease, such as droop, (sweet potato is withered Wither disease, cotton wilt, sesame droop, castor-oil plant droop, tomato wilt, Kidney bean droop, cucumber fusarium axysporum, sponge gourd is withered Wither disease, pumpkin droop, wax gourd droop, watermelon blight, Muskmelon Fusarium wilt, capsicum wilt, faba bean Fusarium wilt, rape is withered Wither disease, soybean Fusariuming disease), root rot (Fusarium solani, eggplant root rot, Kidney bean root rot, cucumber root rot, balsam pear root-rot Disease, cotton black root rot, root rot of Vicia faba), damping-off (cotton seedling blight, sesame damping-off, capsicum damping-off, cucumber rhizoctonia rot, Chinese cabbage damping-off), anthracnose (anthracnose of sorghum, cotton anthracnose, bluish dogbane anthracnose, jute anthracnose, anthracnose of flax, cigarette Careless anthracnose, mulberry anthracnose, pepper anthracnose, eggplant anthracnose, bean anthracnose, cucumber anthracnose, balsam pear anthracnose, western calabash Reed anthracnose, wax gourd anthracnose, watermelon anthrax, muskmelon anthracnose, lichee anthracnose), verticillium wilt (cotton verticillium wilt, Xiang Certain herbaceous plants with big flowers verticillium wilt, tomato verticillium wilt, capsicum verticillium wilt, eggplant verticillium wilt), scab (cucurbita pepo scab, wax gourd scab, sweet tea Melon scab), gray mold (cotton boll gray mold, bluish dogbane gray mold, graw mold of tomato, Botrytis cinerea, Kidney bean gray mold, celery Gray mold, spinach gray mold, Kiwi berry gray mold), brown spot (cotton brown spot, jute brown spot, beet cercospora leaf spot, peanut Brown spot, capsicum brown spot, wax gourd brown spot, soybean brown spot, septorial brown spot of sunflower, pea brown spot, broad bean brown spot), Black spot (flax vacation black spot, alternaria stem rot of colza, sesame black spot, sunflower black spot, castor-oil plant black spot, tomato black spot, Capsicum black spot, eggplant black spot, Kidney bean black spot, cucumber black spot, celery black spot, carrot black rot, carrot blackspot Disease, melanose or canker of apple, the cercospora black spot of peanut), spot blight (spotted wilt of tomato, capsicum spot blight, celery septoria disease), early blight (kind Eggplant early blight, capsicum early blight, eggplant early blight, target, early blight of celery), ring spot (soybean ring spot, sesame Numb ring spot, Kidney bean ring spot), leaf blight (sesame leaf blight, sunflower leaf rot, watermelon leaf blight, muskmelon leaf blight), stem Basal stem rot (tomato base rot disease, Kidney bean base rot disease), and other (Helminthosporium carbonum, bluish dogbane waist folding disease, rice blast, the black sheaths of chestnut Disease, sugarcane eye spot, cotton boll aspergillosis, peanut crown rot, soybean stem wilt, soybean diplostomiasis, muskmelon leaf blight, peanut filigree Disease, the red leaf spot of tea, pepper white star disease, wax gourd leaf spot, celery black rot, spinach heartrot, bluish dogbane leaf mold, bluish dogbane spot Disease, jute stem blight, purple spot of soybean, Alternaria sesami, castor-oil plant graywall, dark brown leaf spot, cercospora leaf spot of egg plant, dish Bean red pinta, balsam pear Leucoplakia, watermelon spot disease, jute withered rotten disease, sunflower root stem rot, Kidney bean charcoal rot, soybean target spot Disease, eggplant rod spore leaf spot, Leaf Spot Caused by Corynespora cassiicola on Cucumber, leaf muld of tomato, eggplant leaf mold, broad bean red spot etc.) etc.；Basidiomycetes disease Evil, such as rust (stripe rust of wheat, the stem rust of wheat, wheat leaf rust, Peanut Rust, rust of sunflower, sugarcane rust, leek Rust, rust of onion, chestnut rust, soybean rust), smut (maize head smut, corn smut, head smut of sorghum, sorghum Smut, covered kernel smut of kaoliang, high beam column smut, chestnut kernel smut, smut of sugarcane, Bean rust disease) and other are (such as small Wheat banded sclerotial blight, rice sheath blight disease etc.) etc.；Sac fungus disease, such as powdery mildew (wheat powdery mildew, rape powdery mildew, sesame white powder Disease, sunflower powdery mildew, beet powdery mildew, eggplant powdery mildew, powdery mildew of pea, sponge gourd powdery mildew, squash marble dust, cucurbita pepo Powdery mildew, wax gourd powdery mildew, melon powdery mildew, uncinula necator, broad bean powdery mildew), sclerotiniose (flax sclerotiniose, Sclerotina Sclerotiorum in Winter Rape Core disease, soybean sclerotinia crown rot, peanut sclerotiniose, tobacco sclerotiniose, capsicum sclerotiniose, eggplant sclerotiniose, bean sclerotinia rot, asparagus pea Core disease, cucumber timberrot, balsam pear sclerotiniose, wax gourd sclerotinia, watermelon sclerotiniose, celery sclerotiniose), scab (the black star of apple Disease, pear scab) etc..

Compound shown in formula I can be used for preventing and treating following insect：

Coleoptera (beetle)：Bean weevil category kind (curculionid), bean weevil (common pea weevil), Emerald ash borer (the narrow Ji of Fraxinus rhynchophylla Fourth), acupuncture needle Eimeria kind (wireworm), anoplophora glabripennis (Asia psacotheahilaris), Anthonomusgrandis category kind of (Culculionidae), Mexico's cotton boll As (bollworm), cocoon honeybee category kind, weevil category kind (curculionid), sugarcane cockchafer category kind (grub), black suede cockchafer (smaller velvety chafer), sweet tea (small beet beetle, cucumber beetle category kind, beet are as (beet root curculionid), bean weevil category kind (curculionid), pea weevil (pea weevil for the hidden food first of dish Worm), Cacoesia category kind, Callosobruchus maculatus (southern cowpea curculionid), pineapple bug (dried-frait beetle), beet tortoise beetle, day Bos Kind, Ccrotoma category kind (chrysomonad), beans chrysomelid (the chrysomelid worm of beans), ceutorhynchus kind (curculionid), Chinese cabbage seed tortoise are as (Chinese cabbage trunk Worm), turnip tortoise is as (cabbage curculionid, phyllotreta (chrysomonad), Colaspis category kind of (a native beetle), Conoderus scala Ris, Conoderus stigmosus, Lee are as (plum bores weevil), Cotinus nitidis (Green june beetle), asparagus scotellaris (asparagus beetle), rusty grain beetle (rust paddy beetle), Cryptolestes pusillus (flat ostomatid), Cryptolestes turcicus Grouville (Turkey Gu Jia Worm), Ctenicera category kind of (nematode), Curculio kind (curculionid), round end rhinoceros cockchafer category kind (grub), close withe be as (to day Certain herbaceous plants with big flowers grass curculionid), mango leaf-cutting is as (mango leaf-cutting curculionid), lader beetle stupid (lader beetle is stupid), white abdomen skin stupid (white abdomen skin is stupid), chrysomelid Category kind (chrysomelid), mexican bean ladybird (Mexico beans beetle), moth stem weevil, pale neck are as (pales weevil), Phytonomus kind (curculionid), alfalfa leaf are as (alfalfa weevil), Hyperdoes category kind (Argentinian stem weevil), the small stupid (coffee of coffee berry Fruit beetle), the small stupid category kind of (spine shin is small stupid) of tooth, lasioderma serricorne (cigarette beetle), colorado potato bug (Colorado potato first Worm), Liogenys f uscus, Liogenys suturalis, the stupid category kind of rice water weevil (rice water weevil), powder (the stupid moth of wood/ The stupid beetle of powder), Maecolaspis joliveti, Megascelis category kind, corn click beetle, nitidulid category plant, rape nitidulid (brevitarsis), May beetle (typical European chafer), Oberea brevis, linear cylinder longicorn, coconut palm moth rhinoceros cockchafer (date palm Beetle), trade saw-toothed grain beetle (market saw-toothed grain beetle), saw-toothed grain beetle (sawtooth paddy beetle), beak weevil category kind of (curculionid), black angle scotellaris (cereal leaf beetle), Oulema oryzae, the short beak of rose as category kind of (curculionid), food phyllobranchia cockchafer category kind (May/June chafer), Phvllophaga cuyabana, striped flea beetle kind (chrysomonad), apple tiger are as category kind, Japan popillia flavosellata fairmaire (Japanese beetle Son), large space between muscles stupid (large space between muscles length stupid), paddy stupid (the small moth of paddy), root gill cockchafer category kind (European chafer), Rhynchophorus kind (as Worm), small stupid category kind (wood stupid a moth), Shenophorus category kind (grain weevil), pea leaf is as (pealeaf weevil), Sitophilus kind (paddy Weevil), grain weevil (paddy worm), rice weevil (rice weevil first), medicinal material ostomatid (Stegobium paniceum), Tribolium kind (flour beetle), red flour beetle (red flour beetle), miscellaneous plan paddy moisten (confused flour beetle), piebald skin stupid (warehouse skin is stupid) and Zabrus tenebioides.

Dermaptera (earwig).Neuroptera (cockroach)：Groton bug (Groton bug), oriental cockroach (oriental cockoach), guest's sunset method The sub- wooden Lian of Buddhist nun, American cockroach (America roach consumptive disease), Australian cockroach (Australian cockroach), periplaneta brunnea (periplaneta brunnea), smoke Perilpaneta americana are (black The big Lian of chest), the green blattaria (sugarcane Lian) of sugarcane and long hair blattaria (brown band blattaria).

Diptera (fly)：Aedes kind (mosquito), alfalfa dive fly (alfalfa dive fly), Hippelates kind (Liriomyza), press Anastrepha kind (drosophila), Caribbean are real by trypetid (pressing trypetid in Caribbean), Anopheles kind (mosquito), Bactrocera kind (drosophila), melon Fly (melon fly), citrus fruit fly (oriental fruit fly), small bar Anastrepha kind (drosophila), the small bar trypetid (medfly) in Mediterranean, spot horsefly Category kind of (a deer horsefly), Callitroga's kind (screw worm fly larva), Ying uranotaenia kind (Ying mosquitos), Culex kind (mosquito), Ye Ying uranotaenia kind (Ying mosquitos), You Cai Ye Ying mosquitos (Juan Xin Cai Ying mosquitos), Delia kind, delia platura (root maggot), Drosophila kind (vinegar fly), Fannia kind (family Fly), anthomyia canicularis (Fannia canicularis), anthomyia scalaris (anthomyia scalaris), big horse botfly (horse botfly), Gracillia perseae, disturb Blood fly (horn fly), Hylemyia kind (root maggot), heel fly (common heel fly), Liriomyza kind (Liriomyza), wild cabbage liriomyza bryoniae (snake Row Liriomyza), sheep hippoboscid (sheepked), fly category kind of (housefly), face fly, housefly, Oestrus ovis (sheep nose fly), European frit fly (Oscinella frit), beet spring fly (spinach leaf miner), wheat fly category kind, carrot fly (carrot rust fly), cherry fruit fly (cherry Drosophila), Rhagoletis pomonella (apple maggots), wheat midge (orange wheat spend on mosquito), tatukira (tatukira), gadfly category kind (horse botfly) With big uranotaenia kind (daddy-longlegs).

Semiptera (stinkbug) (intending acrosternumhilare acrosternumhilare), america valley cinchbug (chinch bug), potato person of outstanding talent fleahopper (potato fleahopper), the torrid zone Bedbug (cimex hemipterus), bedbug (bedbug), Daghertusfasciatus, Dichelops furcatus, the black wing red stinkbug (cotton of cotton Red stinkbug), Edessa meditabunda, Europe Eurygasterspp (paddy worm), Euschistus heros, brown smelly stinkbug (brown stinkbug), iS-One angle Fleahopper, tea angle fleahopper, stinkbug category kind (stinkbug), big Leptocorisa spp, different Leptocorisa spp, Lygus Hahn kind (fleahopper), lygushesperus, the rose of Sharon are graceful Powder stinkbug, Neurocolpus longirostris, green rice bug, Phytocoris kind (fleahopper), California plant fleahopper, Phytocoris relativus, Piezodorus guildingi, four line fleahoppers, Psallus vaccinicola, Pseudacysta perseae, Scaptocoriscastanea and Triatoma kind (cone nose worm of sucking blood hunts stinkbug).

Homoptera (aphid, a red-spotted lizard, aleyrodid, leafhopper)：Acyrthosiphum pisim (acyrthosiphum pisim), adelgid kind, wild cabbage aleyrodid (cabbage powder Lice), Aleurodicus dispersus, velvet aleyrodid (whitefly in bt cotton), white wheel armored scale category kind, Amrascabigut ellabigutella, froghopper category Kind of (leafhopper), California red scale (the red a red-spotted lizard in California, Aphis kind (aphid), cotten aphid, apple aphid, eggplant without net aphid (digitalis aphid), Aleyrodes kind (aleyrodid), Bemisia argentifolii, sweet potato whitefly, Diuraphis noxia (Russian aphid), asparagus tubule aphid (asparagus aphid), Brevennia rehi, brevicoryne brassicae (cabbage aphid), lecanium category kind (a red-spotted lizard), ceroplastes rubens, snow armored scale category kind (a red-spotted lizard), Aspidiotus category kind (a red-spotted lizard), soft wax a red-spotted lizard category kind (a red-spotted lizard), the pink bad aphid of apple, green jassids belong to kind (leafhopper), apple aphid, blow cotton a red-spotted lizard, mango yellow line leaf Cicada, small brown rice planthopper, lepidosaphes shimer kind, long tube Aphis kind, root of Beijing euphorbia Macrosiphus spp (potato aphid), grain aphid (Britain's wheat aphid), rose Macrosiphus spp (rose aphid), four line leafhopper (Aster tataricus leafhopper), Mahanarva frimbiolata, Acyrthosiphon dirhodum (rose wheat Aphid), Midis longicornis, black peach aphid (black peach aphid), rice green leafhopper category kind of (leafhopper), rice green leafhopper (greenery cicada), brown paddy plant hopper, Chaff piece armored scale, ebony armored scale, popcorn wing plant hopper, froghopper category kind (spittle insects), grape phylloxera, Physokermes piceae, stern line mealybug Category kind (mealybug), mealybug category kind (mealybug), the clean mealybug of pineapple, theatre armored scale (san jose scale), aphid a red-spotted lizard category kind (aphid) maize leaves Aphid (corn leaf aphids), rhopalosiphum padi, pearl lecanium category kind (a red-spotted lizard), olive pearl lecanium (black a red-spotted lizard), green bugs (green bugs), wheat long tube Aphid (Britain's wheat aphid), white backed planthopper, variegation Aphis kind (aphid), line lecanium category kind (a red-spotted lizard), sound Aphis kind (aphid), white powder Pediculus Kind (aleyrodid), Trialeurodes vaporariorum Westwood (greenhouse whitefly), knot wing trialeurodes vaporariorum, sharp armored scale category kind (a red-spotted lizard), the sharp clam (arrow a red-spotted lizard) of arrow and Zulia entreriana。

Hymenoptera (Hymenoptera) (ant, wasp and honeybee)：Myrmecina kind, Athaliarosae, leaf ant category kind, Black ant category kind (carpented ant), Diprion kind (sawfly), ant category kind (ant), Argentine ant, Monomorium subspecies, MonomoriumMayr, kitchen ant (little red ant), Neodiprion kind (sawfly), Pogonomyrmex kind (harvester ant), hornet category kind of (wasp), Solenopsis kind (fiery ant), Odorous antenna (odorous antenna), Tetramorium kind (Pavement Ant), Vespula kind (yellow jacket) and Xylocopa kind (carpenter bee).

Isoptera (termite)：Formosanes category kind, bent jaw termite, French termite, coptotermes formosanus, (proboscis is white for angle Cryptotermes kind Ant), sand Cryptotermes kind (dry-wood termite), different Cryptotermes kind (desert Soil termites), golden yellow different termite (kalotermitid category kind (dry wood Termite), principal columns of a hall Cryptotermes kind (dry-wood termite), Macrotermes kind (cultivation termite), ((dry-wood termite), saw are white for edge kalotermitid category kind Ant category kind (careless termite), the small termite of rice wheat, former angle Cryptotermes kind, Reticulitermes kind (Soil termites), Reticulitermes Banyulensis, meadow reticulitermes flavipe, yellow limb reticulitermes flavipe (east Soil termites), beautiful little Huang reticulitermes flavipes, west reticulitermes flavipe (west Soil termites), Sang Te reticulitermes flavipes, the northern reticulitermes flavipe that dwells, U.S. black shin reticulitermes flavipe, U.S. small black reticulitermes flavipe, proboscis Reticulitermes kind and Gu Cryptotermes kind (rotten wood termite).

Lepidoptera (moth and butterfly)：Achoea janata, Adoxophyessp kind, adoxophyes moth, tiger category kind (cut root Worm), small cutworm (black cutworm), cotton leaf ripple noctuid (cotton leafworm), Amorbia cuneana, Amyelosis transi Tella, Anacamptodes defectaria, sliver gelechiid, jute bridge night be high, Anticarsia, fruittree leafroller, rose volume Leaf moth, volume moth category kind, tangerine Argyrotaenia spp (citrus leaf-roller), Autographa gamma, Bonagota cranaodcs, rice are indulged Leaf roll snout moth's larva, cotton leaf lyonetid, thin moth category kind (leaf miner), Capua reticulana, peach fruit moth (peach fruit moth), straw borer spp Kind, Chlumetia transversa Walker, rose Choristoneura spp, Noctua kind, cnaphalocrocis medinalls guenee (meadow leaf roller), beans Pier kind, litchi Branch litchi, the stupid moth of fragrance wood (the stupid moth of wood), Crambus Fabricius kind, Lee's Grapholita spp (Li Guoe), oriental fruit months (eat the heart in east Worm), pod is high for pea moth, the stupid moth of apple ((codling moth), Darna diducta, Diaphania kind (stem borer), snout moth's larva category kind (stem borer), small sugarcane borer, Diatraea grandiosella, Earias kind (bollworm), earias insulana, earias fabia, Ecdytopophaaurantianum, South America maize seedling phycitid, shallow brown apple moth, meal moth category kind (powder snout moth's larva), meal moth, tobacco Meal moth (tobacco snout moth's larva), Mediterranean flour moth, Epimeces category kind, night steinernema, Erionota thorax (Linne), ligustrum fine tortricidae (grape berry Moth), former cutworm, Agrotis kind (cutworm), angle sword Noctua kind (stem borer), east moth fruit moth (the sub- food heart of peach (apricot) Worm), treble cut snout moth (bean pyralid), blue or green Eimeria kind (noctuid), bollworm, paddy reality noctuid (corn borer ridge (snout moth's larva ridge worm/cotton boll Worm)), Heliothis kind (noctuid), tobacco budworm, Hellula undalis, Indarel category kind of (a root moth), the stupid moth of tomato, the white wing of eggplant it is wild Snout moth's larva, pear leaf blister moth, thin moth category kind, grape olethreutid, Loxagrotis category kind (noctuid), beans white line cutworm, gypsymoth, peach Lyonetid (apple leaf miner), oil palm bag moth, Malacosoma kind, lopper worm (dish march moth), beanpod open country snout moth's larva (beans open country snout moth's larva), Bag moth (bagworm), Mythimna unipuncta, Neoleucinodes elegantalis (small tomato moth), 3 water Snout moth's larva (rice leaf roller), winter looper, European corn borer (European corn borer), Oxydia vesulia, the brown volume moth (common glucose of boundary Leaf roller), apple brown bortrix, African Bodhidharma swallowtail butterfly, Pectinophora gossypiella (pink bollworm), boundary Noctua kind (cutworm), variegated cutworm, Coffee leafminer, phthorimaea operculella, citrus leaf lyonetid, thin moth category kind (leaf miner), cabbage butterfly (external cabbage caterpillar), head are by green Noctuid, India paddy spot moth, diamond-back moth, grape berry moth, tangerine fruit ermine moth, olive ermine moth, mythimna separata category kind of (noctuid), Pseudaletiaunipunctata (armyworm), soybean noctuid, looper, yellow rice borer, moth stem night high category kind (stem borer), rice moth Stem noctuid, powder stem snout moth's larva, the brown slug moth of copper stain, gelechiid, pilleriana, Spodoptera kind (armyworm), beet armyworm (beet Armyworm), Spodopterafrugiperda (autumn armyworm), southern spodoptera (southern armyworm), emerging Noctua kind (root moth), Thecla basilides, Thermisia gemmatalis, casemaking clothes moth, cabbage looper, Liriomyza brponiae, Yponomeuta kind, coffee The stupid moth of leopard and Zeuzera pyrina (the stupid moth of pears leopard).

Mallophaga (poultry louse)：Sheep poultry louse, fiery menopon gallinae (chick poultry louse) and shaft louse (common hen house).

Orthoptera (grasshopper, locust and cricket)：Blackspot arna Zhong (rub a katydid), mole cricket (mole cricket), Asiatic migrotory locust, grasshopper Category kind of (grasshopper), guiding principle wing spinelet Zhong (angle wing katydid), Pterophylla category kind (katydid), chistocerca gregaria, Fork-tail katydid (fork-tail shrubbery tree Zhong) and black angle oncus locust.

Anoplura (sucks lice)：Pediculus of sucking blood kind (ox louse and pig lice), sheep jaw lice (sheep lice), head louse (body louse), pediculus humanus corporis (body louse) and crab louse (crab louse).

Siphonaptera (flea)：Ctenocephalides canis, ctenocephalides felis and Pulex irritans.

Thysanoptera (thrips)：Cigarette brown thrip, western classical architecture, Frankliniella shultzei, Williams flower thrips (corn thrips), greenhouse thrips, Riphiphorothrips cruentatus, hard Thrips kind, balloonflower root thrips, Scirothrips dorsalis, Taeniothrips rhopalantennalis and Thrips kind.

Thysanoptera (moth)：Silverfish category kind (stupid worm) and special mess silverfish category kind (special mess fish).

Acarina (mite and cicada)：Wu Shi honeybee shields mite (honeybee Tracheal mite), Tyroglyphus kind (food mites), Acarus siro (paddy mite), mango bud mite, peronium Eriophyes kind, Aculops lycopersici, Aculops pelekasi, tangerine peronium goitre mite, Si Shi thorns Goitre mite (apple thorn goitre mite), lone star tick, Boophilus kind (tick), avette short hairs tick, purplish red short hairs mite, fat tick category kind, Dermacentor kind (hard tick), America dog tick, dermatophagoides pteronyssinus, Eotetranychus kind, Eotetranychus carpini (yellow spider mite), Epitrimerus kind, Eriophyes kind, Isodesspp kind (tick), Panonychus citri category kind, notoedres cati, Oligonychus kind, coffee unguiculus mite, ilex Oligonychus, Panonychus citri category kind, tangerine It is Panonychus citri (orange spider), panonychus ulmi (European red spider), tangerine wrinkle leaf thorn goitre, Polyphagotarsonemus latus Banks (broad mite), blood red Fan head tick (brown dog tick, root mite category kind (root mite), itch mite, avocado apical cap goitre mite, Tetranychus kind, T.urticae Koch (2 spider mites) With Di Shi watts of mite (honeybee mite).

Nematoda (nematode)：Aphelenchoides kind (bud and leaf and pine wood nematode, thorn Turbatrix kind, small loop wire Eimeria kind, Heart worm, Ditylenchus kind (stem and bulb eelworm), spine rubber-insulated wire Eimeria kind, corn SCN, Hirschmanniella kind, tie Turbatrix kind, Meloidogyne kind (root-knot nematode), Meloidogyne incognita (root-knot nematode), Onchocerca caecutiens, Pratylenchus Kind rotten nematode, perforation line Eimeria kind similes thorne and banana reniform nematode.

Symphyla (comprehensive insects)：Kahikatea worm.

Due to its positive characteristic, above-claimed cpd is advantageously used for protection agricultural and the important crop of horticulture, family Poultry and breeding stock, and the environment that the mankind often go is from germ, the injury of insect evil mite.

To obtain ideal effect, the dosage of compound changes because of various factors, such as compound used therefor, the work protected in advance Thing, the type of harmful organism, gradient of infection, weather conditions, application method, the formulation used.

The compound dosage of 10 grams -5 kilograms of per hectare can provide sufficient preventing and treating.

Present invention additionally comprises the sterilization using compound shown in formula I as active component, insecticide acaricide composition.This is killed The weight percentage of active component is between 0.5-99% in bacterium, insecticide acaricide composition.The sterilization, insecticide acaricide composition In also include agricultural, forestry, acceptable carrier in health.

The composition of the present invention can be applied in the form of preparation.Compound shown in formula I dissolves or divided as active component It is more readily dispersible when dissipating in carrier or being configured to preparation to be used as sterilization, desinsection.Such as：These chemicals can quilt Wettable powder, oil suspending agent, aqueous suspension, aqueous emulsion, aqua or missible oil etc. is made.In these compositions, at least add a kind of Liquid or solid carrier, and appropriate surfactant can be added when needed.

Technical scheme also includes anti-pathogen, the method for insect evil mite：By the sterilization of the present invention, Insecticiding-miticiding Composition is imposed on described germ or its somatomedin.The more suitable effective amount generally selected is per hectare 10 grams to 1000 Gram, preferably effective dose is 20 grams to 500 grams of per hectare.

For some applications, for example, agriculturally can the sterilization of the present invention, add in insecticide acaricide composition it is a kind of or A variety of other bactericide, insecticidal/acaricidal agent, herbicide, plant growth regulator or fertilizer etc., thus it can produce additional excellent Point and effect.

Embodiment

Specific examples below is used for further illustrating the present invention, but the present invention be only limitted to absolutely not these examples (except as otherwise Outside indicating, all raw materials are commercially available).

Following methods are analyzed for LC-MS：

Chromatographic column：Agilent ZORBAX SB-C18 150mm × 4.6mm, 5 μm (i.d)；

Detection wavelength：254nm；Flow velocity：1.0mL/min；Column temperature：30℃；

Condition of gradient elution：

Time (min)	Acetonitrile (%)	0.1% aqueous formic acid (%)
			0.00	30	70
8.00	30	70
			15.00	70	30
25.00	70	30

Embodiment 1

3- (((2- diuril azoles -5- bases) methyl) (methyl) amido) benzisothiazole 1,1- dioxide (compound 1)

1. 3- chlorine benzisothiazole 1,1- dioxide

At room temperature, by the dioxide of 36.6g (0.20mol) benzisothiazole -3 (2H) -one 1,1,71.4g (0.6mol) Thionyl chloride is dissolved in back flow reaction 12 hours in 100ml dioxane, the monitoring of TLC plates, remaining a small amount of raw material successively.Decompression is de- Except solvent, residue 60ml re crystallization from toluene, filter, drying, obtain white solid 30g, yield：75%, fusing point 148-149 ℃。

1- 2. (2- diuril azoles -5- bases)-nitrogen-methyl methylamine

At room temperature, the methylamine water solutions of 82g (0.8mol) 30% are added in the ethanol of 120ml 95%, are cooled to 0 DEG C.Upwards Dropwise addition 34g (0.2mol) 2- chloro-5-chloromethyl thiazoles in solution are stated, below 5 DEG C used time 1h is added dropwise, after dripping off in temperature control Continue to stir 1h at 0 DEG C.Progressively it is warmed to room temperature, continues to stir 3h.TLC is detected, and raw material reaction finishes.Reaction solution is concentrated under reduced pressure, 100ml water is added in residue, is extracted with ethyl acetate (3x50ml), combining extraction liquid, the washing of 50ml saturated common salts is anhydrous Magnesium sulfate is dried, and filtering, is concentrated under reduced pressure, is obtained product 30g, yield 92%.

3- 3. (((2- diuril azoles -5- bases) methyl) (methyl) amido) benzisothiazole 1,1- dioxide

At room temperature, by the sodium hydrides of 0.9g (0.022mol) 60%, 4.8g (0.015mol) 1- (2- diuril azoles -5- bases)-nitrogen - Methyl methylamine is dissolved in 30ml acetonitriles successively, stirs 10 minutes at room temperature.3.1g (0.015mol) is added into said mixture 3- chlorine benzisothiazole 1,1- dioxide, is warming up to back flow reaction 8h.TLC plates monitor, raw material 3- chlorine benzisothiazole 1,1- Dioxide reaction finishes.Reactant mixture is cooled to room temperature, filters, filter cake 20ml acetonitrile diafiltrations, merging filtrate.Filtrate decompression Desolvation, 50ml water is added into gained residue, extracted with ethyl acetate (3x30ml), combining extraction liquid, 50ml saturations Salt is washed, and anhydrous magnesium sulfate is dried, and filtering, is concentrated under reduced pressure, is obtained crude product.Recrystallized with 95% ethanol 25g, it is faint yellow to obtain 3g Solid, as title compound, yield 61%.Fusing point：208-210℃.

LC/MS[M+H]⁺=327.99, [M+Na]⁺=349.97, [M+K]⁺=365.95.

Embodiment 2

3- (((2- diuril azoles -5- bases) methyl) (methyl) amido) benzisothiazole 1,1- dioxide (compound 16)

N- 1. ((2- diuril azoles -5- bases)-methyl) ethamine

At room temperature, the ethylamine solutions of 13.8g (0.2mol) 65% are added in the ethanol of 50ml 95%, are cooled to 0 DEG C.To 8.5g (0.05mol) 2- chloro-5-chloromethyl thiazoles are added dropwise in above-mentioned solution, used time 1h, drop is added dropwise below 5 DEG C in temperature control Continue to stir 1h at 0 DEG C after complete.Progressively it is warmed to room temperature, continues to stir 5h.TLC is detected, and starting material left is a small amount of.Reaction solution decompression is dense Contract, 50ml water is added in residue, extracted with ethyl acetate (3x30ml), combining extraction liquid, the washing of 30ml saturated common salts, nothing Water magnesium sulfate is dried, and filtering, is concentrated under reduced pressure, is obtained product 7.5g, yield 85%.

3- 2. (((2- diuril azoles -5- bases) methyl) (ethyl) amido) benzisothiazole 1,1- dioxide

At room temperature, by the sodium hydrides of 0.9g (0.022mol) 60%, 4.8g (0.015mol) N- ((2- diuril azoles -5- bases)-first Base) ethamine is dissolved in 30ml acetonitriles successively, stirs 10 minutes at room temperature.3.1g (0.015mol) 3- is added into said mixture Chlorine benzisothiazole 1,1- dioxide, it is warming up to back flow reaction 5h.TLC plates monitor, raw material 3- chlorine benzisothiazole 1,1- bis- Oxide reaction finishes.Reactant mixture is cooled to room temperature, filters, filter cake 20ml acetonitrile diafiltrations, merging filtrate.Filtrate decompression takes off Except solvent, 50ml water is added into gained residue, is extracted with ethyl acetate (3x30ml), combining extraction liquid, 50ml saturations food Salt is washed, and anhydrous magnesium sulfate is dried, and filtering, is concentrated under reduced pressure, is obtained crude product.Recrystallized with 95% ethanol 8g, obtain 1.1g milkys Solid, as product, yield 22%.Fusing point：213-215℃.

LC/MS[M+H]⁺=342.01, [M+Na]⁺=363.99, [M+K]⁺=379.97.

Embodiment 3

3- (((2- diuril azoles -5- bases) methyl) (methoxyl group) amido) benzisothiazole 1,1- dioxide (compounds 106)

N- 1. ((2- diuril azoles -5- bases)-methyl)-oxygen-methylhydroxylamine

At room temperature, 8.5g (0.1mol) methoxy amine hydrochlorate, 22g (0.21mol) triethylamine are added to 80ml acetonitriles In, it is cooled to 0 DEG C.Into above-mentioned solution be added dropwise the chloro- 5- 5-chloromethyl thiazoles of 16.8g (0.1mol) 2-, temperature control below 5 DEG C, Used time 1.5h is added dropwise, is progressively warmed to room temperature after dripping off, continues to stir 2h.50 DEG C are warming up to continue to stir 4h.TLC detection raw materials remain It is remaining a small amount of.Reaction solution is down to room temperature, is concentrated under reduced pressure, and 50ml water is added in residue, is extracted with ethyl acetate (3x50ml), merges Extract, the washing of 50ml saturated common salts, anhydrous magnesium sulfate are dried, filtering, are concentrated under reduced pressure, obtain product 5.5g, yield 30%.

3- 2. (((2- diuril azoles -5- bases) methyl) (methoxyl group) amido) benzisothiazole 1,1- dioxide

At room temperature, by the sodium hydrides of 0.9g (0.022mol) 60%, 2.7g (0.015mol) N- ((2- diuril azoles -5- bases)-first Base)-oxygen-methylhydroxylamine is dissolved in 30ml acetonitriles successively, stirs 10 minutes at room temperature.3.1g is added into said mixture (0.015mol) 3- chlorine benzisothiazole 1,1- dioxide, is warming up to back flow reaction 6h.TLC plates monitor, and raw material 3- chlorobenzenes are simultaneously Isothiazole 1,1- dioxide is remaining on a small quantity.Reactant mixture is cooled to room temperature, filters, filter cake 20ml acetonitrile diafiltrations, merges filter Liquid.Filtrate decompression desolvation, 50ml water is added into gained residue, extracted with ethyl acetate (3x30ml), merge extraction Liquid, the washing of 50ml saturated common salts, anhydrous magnesium sulfate are dried, filtering, are concentrated under reduced pressure, obtain crude product.Column chromatography (eluant, eluent：Acetic acid second The mixed liquor (1 of ester and petroleum ether：1) 1.5g title compounds, yield 29%) are obtained.Fusing point：218-220℃.

LC/MS[M+H]⁺=343.99, [M+Na]⁺=365.97, [M+K]⁺=381.95.

Embodiment 4

3- (((2- diuril azoles -5- bases) methyl) (isopropyl) amido) benzisothiazole 1,1- dioxide (compound 46)

N- 1. ((2- diuril azoles -5- bases)-methyl) propane -2- amine

At room temperature, 11.8g (0.2mol) isopropylamine is added in the ethanol of 50ml 95%, is cooled to 0 DEG C.To above-mentioned solution Middle dropwise addition 8.5g (0.05mol) 2- chloro-5-chloromethyl thiazoles, temperature control are added dropwise used time 1h, continue 0 after dripping off below 5 DEG C 1h is stirred at DEG C.Progressively it is warmed to room temperature, continues to stir 6h.TLC is detected, and raw material reaction finishes.Reaction solution is concentrated under reduced pressure, residue Middle addition 50ml water, extracted with ethyl acetate (3x30ml), combining extraction liquid, 50ml saturated common salts washing, anhydrous magnesium sulfate is done It is dry, filtering, it is concentrated under reduced pressure, obtains product 7.6g, yield 80%.

3- 2. (((2- diuril azoles -5- bases) methyl) (isopropyl) amido) benzisothiazole 1,1- dioxide

At room temperature, by the sodium hydrides of 0.9g (0.022mol) 60%, 2.9g (0.015mol) N- ((2- diuril azoles -5- bases)-first Base) propane -2- amine is dissolved in 30ml acetonitriles successively, stirs 10 minutes at room temperature.3.1g is added into said mixture (0.015mol) 3- chlorine benzisothiazole 1,1- dioxide, is warming up to back flow reaction 5h.TLC plates monitor, and raw material 3- chlorobenzenes are simultaneously Isothiazole 1,1- dioxide is remaining on a small quantity.Reactant mixture is cooled to room temperature, filters, filter cake 20ml acetonitrile diafiltrations, merges filter Liquid.Filtrate decompression desolvation, 50ml water is added into gained residue, extracted with ethyl acetate (3x30ml), merge extraction Liquid, the washing of 50ml saturated common salts, anhydrous magnesium sulfate are dried, filtering, are concentrated under reduced pressure, obtain crude product.Column chromatography (eluant, eluent：Acetic acid second The mixed liquor (1 of ester and petroleum ether：2) 1.5g title compounds, yield 30%) are obtained.Fusing point：211-213℃.

LC/MS[M+H]⁺=353.02, [M+Na]⁺=378.00, [M+K]⁺=393.98.

Embodiment 5

3- (sec-butyl ((2- diuril azoles -5- bases) methyl) amido) benzisothiazole 1,1- dioxide (compound 131)

N- 1. ((2- diuril azoles -5- bases)-methyl) butane -2- amine

At room temperature, 14.6g (0.2mol) isobutyl amine is added in the ethanol of 50ml 95%, is cooled to 0 DEG C.To above-mentioned solution Middle dropwise addition 8.5g (0.05mol) 2- chloro-5-chloromethyl thiazoles, temperature control are added dropwise used time 1h, continue 0 after dripping off below 5 DEG C 1h is stirred at DEG C.40 DEG C are progressively risen to, continues to stir 6h.TLC is detected, and raw material reaction finishes.Reaction solution is concentrated under reduced pressure, remaining 50ml water is added in thing, is extracted with ethyl acetate (3x30ml), combining extraction liquid, the washing of 50ml saturated common salts, anhydrous magnesium sulfate Dry, filtering, be concentrated under reduced pressure, obtain product 7.9g, yield 78%.

3- 2. (sec-butyl ((2- diuril azoles -5- bases) methyl) amido) benzisothiazole 1,1- dioxide

At room temperature, by the sodium hydrides of 0.9g (0.022mol) 60%, 3.1g (0.015mol) N- ((2- diuril azoles -5- bases)-first Base) butane -2- amine is dissolved in 30ml acetonitriles successively, stirs 10 minutes at room temperature.3.1g is added into said mixture (0.015mol) 3- chlorine benzisothiazole 1,1- dioxide, is warming up to back flow reaction 6h.TLC plates monitor, and raw material 3- chlorobenzenes are simultaneously Isothiazole 1,1- dioxide is remaining on a small quantity.Reactant mixture is cooled to room temperature, filters, filter cake 20ml acetonitrile diafiltrations, merges filter Liquid.Filtrate decompression desolvation, 50ml water is added into gained residue, extracted with ethyl acetate (3x30ml), merge extraction Liquid, the washing of 50ml saturated common salts, anhydrous magnesium sulfate are dried, filtering, are concentrated under reduced pressure, obtain crude product.Column chromatography (eluant, eluent：Acetic acid second The mixed liquor (1 of ester and petroleum ether：2) 1.8g title compounds, yield 32%) are obtained.Fusing point：216-218℃.

LC/MS[M+H]⁺=370.04, [M+Na]⁺=392.02, [M+K]⁺=408.00.

Embodiment 6

2- (((2- diuril azoles -5- bases) methyl) (1,1- dioxy benzisothiazole -3- bases) amido) acetonitrile (compound 76)

2- 1. (((2- diuril azoles -5- bases)-methyl) amine) acetonitrile

At room temperature, 9.3g (0.1mol) aminoacetonitrile HCl salt, 22g (0.2mol) triethylamine are added to 30ml successively In 95% ethanol, it is cooled to 0 DEG C.8.5g (0.05mol) 2- chloro-5-chloromethyl thiazoles are added dropwise into above-mentioned solution, temperature control exists Less than 5 DEG C, used time 1h is added dropwise, continues to stir 1h at 0 DEG C after dripping off.40 DEG C are progressively warming up to, continues to stir 5h.TLC is detected, former Material reaction finishes.Reaction solution is concentrated under reduced pressure, and 50ml water is added in residue, is extracted with ethyl acetate (3x30ml), merges extraction Liquid, the washing of 50ml saturated common salts, anhydrous magnesium sulfate are dried, filtering, are concentrated under reduced pressure, obtain product 6.6g, yield 71%.

2- 2. (((2- diuril azoles -5- bases) methyl) (1,1- dioxy benzisothiazole -3- bases) amido) acetonitrile

At room temperature, by the sodium hydrides of 0.9g (0.022mol) 60%, 2.8g (0.015mol) 2- (((2- diuril azoles -5- bases) - Methyl) amine) acetonitrile is dissolved in 30ml acetonitriles successively, stirs 10 minutes at room temperature.3.1g is added into said mixture (0.015mol) 3- chlorine benzisothiazole 1,1- dioxide, is warming up to back flow reaction 5h.TLC plates monitor, and raw material 3- chlorobenzenes are simultaneously Isothiazole 1,1- dioxide is remaining on a small quantity.Reactant mixture is cooled to room temperature, filters, filter cake 20ml acetonitrile diafiltrations, merges filter Liquid.Filtrate decompression desolvation, 50ml water is added into gained residue, extracted with ethyl acetate (3x30ml), merge extraction Liquid, the washing of 50ml saturated common salts, anhydrous magnesium sulfate are dried, filtering, are concentrated under reduced pressure, obtain crude product.Column chromatography (eluant, eluent：Acetic acid second The mixed liquor (1 of ester and petroleum ether：2) 1.1g title compounds, yield 29%) are obtained.Fusing point>250℃.

LC/MS[M+H]⁺=352.99, [M+Na]⁺=374.97, [M+K]⁺=390.95.

Embodiment 7

3- (((2- diuril azoles -5- bases) methyl) (cyclopropyl) amido) benzisothiazole 1,1- dioxide (compounds 61)

N- 1. ((2- diuril azoles -5- bases)-methyl) cyclopropylamine

At room temperature, 11.8g (0.2mol) isopropylamine is added in the ethanol of 50ml 95%, is cooled to 0 DEG C.To above-mentioned solution Middle dropwise addition 8.5g (0.05mol) 2- chloro-5-chloromethyl thiazoles, temperature control are added dropwise used time 1h, continue 0 after dripping off below 5 DEG C 1h is stirred at DEG C.Progressively it is warmed to room temperature, continues to stir 6h.TLC is detected, and raw material reaction finishes.Reaction solution is concentrated under reduced pressure, remaining 50ml water is added in thing, is extracted with ethyl acetate (3x30ml), combining extraction liquid, the washing of 50ml saturated common salts, anhydrous magnesium sulfate Dry, filtering, be concentrated under reduced pressure, obtain product 7.6g, yield 80%.

3- 2. (((2- diuril azoles -5- bases) methyl) (cyclopropyl) amido) benzisothiazole 1,1- dioxide

At room temperature, by the sodium hydrides of 0.9g (0.022mol) 60%, 2.8g (0.015mol) N- ((2- diuril azoles -5- bases)-first Base) cyclopropylamine is dissolved in 30ml acetonitriles successively, stirs 10 minutes at room temperature.3.1g (0.015mol) is added into said mixture 3- chlorine benzisothiazole 1,1- dioxide, is warming up to back flow reaction 5h.TLC plates monitor, raw material 3- chlorine benzisothiazole 1,1- Dioxide is remaining on a small quantity.Reactant mixture is cooled to room temperature, filters, filter cake 20ml acetonitrile diafiltrations, merging filtrate.Filtrate decompression Desolvation, 50ml water is added into gained residue, extracted with ethyl acetate (3x30ml), combining extraction liquid, 50ml saturations Salt is washed, and anhydrous magnesium sulfate is dried, and filtering, is concentrated under reduced pressure, is obtained crude product.Column chromatography (eluant, eluent：Ethyl acetate and petroleum ether Mixed liquor (1：1.5) 1.5g title compounds, yield 28%) are obtained.Fusing point：228-230℃.

LC/MS[M+H]⁺=354.01, [M+Na]⁺=375.99, [M+K]⁺=391.97.

Embodiment 8

Nitrogen-((2- diuril azoles -5- bases) methyl)-nitrogen-(1,1- dioxy benzisothiazole -3- bases) cyanamide (compound 91)

1. nitrogen-((2- diuril azoles -5- bases)-methyl) cyanamide

At room temperature, the cyanamide aqueous solution of 11.2g (0.1mol) 50%, 22g (0.2mol) triethylamine are added to successively In the ethanol of 30ml 95%, it is cooled to 0 DEG C.8.5g (0.05mol) 2- chloro-5-chloromethyl thiazoles, temperature are added dropwise into above-mentioned solution Used time 1h is added dropwise below 5 DEG C in control, continues to stir 1h at 0 DEG C after dripping off.Progressively it is warmed to room temperature, continues to stir 6h.TLC is examined Survey, raw material reaction finishes.Reaction solution is concentrated under reduced pressure, and 50ml water is added in residue, is extracted with ethyl acetate (3x30ml), is merged Extract, the washing of 50ml saturated common salts, anhydrous magnesium sulfate are dried, filtering, are concentrated under reduced pressure, obtain product 5.6g, yield 65%.

2. nitrogen-((2- diuril azoles -5- bases) methyl)-nitrogen-(1,1- dioxy benzisothiazole -3- bases) cyanamide

At room temperature, by the sodium hydrides of 0.9g (0.022mol) 60%, 2.6g (0.015mol) nitrogen-((2- diuril azoles -5- bases) - Methyl) cyanamide is dissolved in 30ml acetonitriles successively, stirs 10 minutes at room temperature.3.1g (0.015mol) is added into said mixture 3- chlorine benzisothiazole 1,1- dioxide, is warming up to back flow reaction 5h.TLC plates monitor, raw material 3- chlorine benzisothiazole 1,1- Dioxide is remaining on a small quantity.Reactant mixture is cooled to room temperature, filters, filter cake 20ml acetonitrile diafiltrations, merging filtrate.Filtrate decompression Desolvation, 50ml water is added into gained residue, extracted with ethyl acetate (3x30ml), combining extraction liquid, 50ml saturations Salt is washed, and anhydrous magnesium sulfate is dried, and filtering, is concentrated under reduced pressure, is obtained crude product.Column chromatography (eluant, eluent：Ethyl acetate and petroleum ether Mixed liquor (1：2) 1.2g title compounds, yield 24%) are obtained.Fusing point：239-241℃.

LC/MS[M+H]⁺=338.97, [M+Na]⁺=360.95, [M+K]⁺=376.93.

Embodiment 9

3- (((2,4- dichloro thiazole -5- bases) methyl) (methyl) amido) benzisothiazole 1,1- dioxide (compounds 2)

1- 1. (2,4- dichloro thiazole -5- bases)-nitrogen-methyl methylamine

At room temperature, the methylamine water solutions of 82g (0.8mol) 30% are added in the ethanol of 120ml 95%, are cooled to 0 DEG C.Upwards Dropwise addition bis- chloro- 5- bromomethyls thiazoles of 50g (0.2mol) 2,4- in solution are stated, used time 1h, drop is added dropwise below 5 DEG C in temperature control Continue to stir 1h at 0 DEG C after complete.Progressively it is warmed to room temperature, continues to stir 3h.TLC is detected, and raw material reaction finishes.Reaction solution decompression is dense Contract, 100ml water is added in residue, extracted with ethyl acetate (3x50ml), combining extraction liquid, the washing of 50ml saturated common salts, nothing Water magnesium sulfate is dried, and filtering, is concentrated under reduced pressure, is obtained product 35g, yield 88%.

3- 3. (((2,4- dichloro thiazole -5- bases) methyl) (methyl) amido) benzisothiazole 1,1- dioxide

At room temperature, by the sodium hydrides of 0.9g (0.022mol) 60%, 2.9g (0.015mol) 1- (2,4- dichloro thiazole -5- Base)-nitrogen-methyl methylamine is dissolved in 30ml acetonitriles successively, stirs 10 minutes at room temperature.3.1g is added into said mixture (0.015mol) 3- chlorine benzisothiazole 1,1- dioxide, is warming up to back flow reaction 8h.TLC plates monitor, and raw material 3- chlorobenzenes are simultaneously The reaction of isothiazole 1,1- dioxide finishes.Reactant mixture is cooled to room temperature, filters, filter cake 20ml acetonitrile diafiltrations, merges filter Liquid.Filtrate decompression desolvation, 50ml water is added into gained residue, extracted with ethyl acetate (3x30ml), merge extraction Liquid, the washing of 50ml saturated common salts, anhydrous magnesium sulfate are dried, filtering, are concentrated under reduced pressure, obtain crude product.Recrystallized with 95% ethanol 25g, Obtain 2.7g faint yellow solids, as title compound, yield 50%.Fusing point：229-231℃.

LC/MS[M+H]⁺=361.95, [M+Na]⁺=383.93, [M+K]⁺=399.91.

Embodiment 10

3- (((2,4- dichloro thiazole -5- bases) methyl) (ethyl) amido) benzisothiazole 1,1- dioxide (compounds 17)

N- 1. ((2,4- dichloro thiazole -5- bases)-methyl) ethamine

At room temperature, the ethylamine solutions of 13.8g (0.2mol) 65% are added in the ethanol of 50ml 95%, are cooled to 0 DEG C.To Bis- chloro- 5- bromomethyls thiazoles of 12.3g (0.05mol) 2,4- are added dropwise in above-mentioned solution, the used time is added dropwise below 5 DEG C in temperature control 1h, continue to stir 1h at 0 DEG C after dripping off.Progressively it is warmed to room temperature, continues to stir 5h.TLC is detected, and starting material left is a small amount of.Reaction solution It is concentrated under reduced pressure, 50ml water is added in residue, is extracted with ethyl acetate (3x30ml), combining extraction liquid, 30ml saturated aqueous common salts Wash, anhydrous magnesium sulfate is dried, and filtering, is concentrated under reduced pressure, is obtained product 8.9g, yield 85%.

3- 2. (((2,4- dichloro thiazole -5- bases) methyl) (ethyl) amido) benzisothiazole 1,1- dioxide

At room temperature, by the sodium hydrides of 0.9g (0.022mol) 60%, 3.2g (0.015mol) N- ((2,4- dichloro thiazole -5- Base)-methyl) ethamine is dissolved in 30ml acetonitriles successively, stirs 10 minutes at room temperature.3.1g is added into said mixture (0.015mol) 3- chlorine benzisothiazole 1,1- dioxide, is warming up to back flow reaction 5h.TLC plates monitor, and raw material 3- chlorobenzenes are simultaneously The reaction of isothiazole 1,1- dioxide finishes.Reactant mixture is cooled to room temperature, filters, filter cake 20ml acetonitrile diafiltrations, merges filter Liquid.Filtrate decompression desolvation, 50ml water is added into gained residue, extracted with ethyl acetate (3x30ml), merge extraction Liquid, the washing of 50ml saturated common salts, anhydrous magnesium sulfate are dried, filtering, are concentrated under reduced pressure, obtain crude product.Recrystallized, obtained with 95% ethanol 8g To 1.9g faint yellow solids, as title compound, yield 33%.Fusing point：234-236℃.

LC/MS[M+H]⁺=375.97, [M+Na]⁺=397.95, [M+K]⁺=413.93.

Embodiment 11

3- (((6- chloropyridine -3- bases) methyl) (methyl) amido) benzisothiazole 1,1- dioxide (compound 344)

1. 3- chlorine benzisothiazole 1,1- dioxide

At room temperature, by the dioxide of 36.6g (0.20mol) benzisothiazole -3 (2H) -one 1,1,71.4g (0.6mol) chlorine Change sulfoxide and be dissolved in back flow reaction 12 hours in 100ml dioxane, the monitoring of TLC plates, remaining a small amount of raw material successively.Removed under reduced pressure Solvent, residue 60ml re crystallization from toluene, filter, drying, obtain white solid 30g, yield：75%, 148-149 DEG C of fusing point.

3- 2. (((6- chloropyridine -3- bases) methyl) (methyl) amido) benzisothiazole 1,1- dioxide

At room temperature, by 4.1g (0.02mol) 3- chlorine benzisothiazole 1,1- dioxide, 3.4g (0.02mol) 1- (6- Chloropyridine -3- bases)-nitrogen-methylmethane and 3g (0.03mol) triethylamine be dissolved in 30ml acetonitriles, and gained mixture is warming up to back Stream reaction 6 hours, the monitoring of TLC plates, raw material 3- chlorine benzisothiazole 1, the reaction of 1- dioxide finish.Reactant mixture is cooled to room Temperature, filter, filter cake 20ml acetonitrile diafiltrations, merging filtrate.Filtrate decompression desolvation, 50ml is added into gained residue Water, extracted with ethyl acetate (3x20ml), combining extraction liquid, 50ml saturated common salts washing, anhydrous magnesium sulfate is dried, and filtering, is subtracted Pressure concentration, obtains crude product, column chromatography (eluant, eluent：The mixed liquor (1 of ethyl acetate and petroleum ether：1) 1.65g title compounds) are obtained Thing, yield 26%.Fusing point： 235-237℃.

LC/MS[M+H]⁺=322.04, [M+Na]⁺=344.02, [M+K]⁺=359.99.

Other compounds of the present invention synthesize with reference to the above method.

The LC/MS data for the compound of Formula I being related in other parts table 1 are as shown in table 2：

The LC/MS data for the compound of Formula I being related in the part table 1 of table 2

Biological activity determination：The compounds of this invention is all shown very well to a variety of germs in agriculture field, insect evil mite Activity.

1. bactericidal activity determines

The compounds of this invention has carried out Antifungal Activity in Vitro or the experiment of live body protecting effect to a variety of fungal diseases of plant. Bactericidal activity measurement result is shown in following embodiment.

In vitro bactericidal activity measure：Method of testing is as follows, by the test compound sample solvent (kind of solvent being adapted to Class such as acetone, methanol, DMSO etc., and selected according to its solvability to sample) dissolving, it is to be measured to be configured to required concentration Liquid.Under ultra-clean working environment, prepare liquid is added in the micropore of 96 well culture plates, then pathogen is bred into liquid suspension It is added thereto, the culture plate after processing, which is placed in constant incubator, to be cultivated.Periodically investigated, it is numerous that pathogen is estimated during investigation Body sprouting or growing state, and the sprouting according to control treatment or growing state are grown, evaluates compound bacteriostatic activity.

The indoor biometricses method of specific germ：Poison of the medicament to certain germ is determined using plate mycelial growth rate method Power.It is specific as follows：Certain germ bacterial strain PDA culture medium culture through switching activation, treats that bacterium colony length is big to culture dish 3/4ths Hour, punched with the card punch that internal diameter is 5mm from edge, the mycelia block broken into is as inoculum.By medicament mother liquor with 0.1% The Tween 80 aqueous solution is diluted to 5-7 mass concentration, then adds in the PDA culture medium that people's sterilizing is melted, and fully shakes up, phase is made Answer the drug containing flat board of concentration.15mL or so pastille culture mediums are poured into per ware, if the processing without medicament is blank control, are often handled 4 repetitions.The mycelia block (diameter 5mm) that transposing newly grows in flat board center, after be placed in culture 7d in 25 DEG C of incubators.Handed over cross Fork method measures colony diameter, calculates each processing net growth, mycelial growth inhibition rate.

Mycelial growth inhibition rate (%)=[(control colony diameter-bacteria cake diameter)-(processing colony diameter-bacteria cake is straight Footpath)]/(control colony diameter-bacteria cake diameter) × 100.

In formula：Bacteria cake diameter is 5mm.

Data statistic analysis：Mycelial growth inhibition rate is converted into probit value (y), drug concentration (μ g/mL) is converted into pair Numerical value (x), virulence regression equation (y=a+bx) is tried to achieve with least square method.With DPS statistical softwares to each single dose and different mixtures Log concentration value and corresponding inhibiting rate probit value carry out regression analysis, calculate EC₅₀Value and 95% confidence limit.

Conclusion (of pressure testing)

(1) to Pyricularia oryzae (Magna porthe oryzae B.C.Couch) Antifungal Activity in Vitro part of detecting chemical combination The Antifungal Activity in Vitro (being represented with inhibiting rate) to Pyricularia oryzae (Magna porthe oryzae B.C.Couch) of thing is tested As a result it is as follows：

Under 100ppm dosage, have to the compound of the inhibiting rate of rice blast more than 90%：1、2、 3、8、10、11、 15、16、17、23、30、46、61、76、77、91、106、131、161、167、194、198、209、239、352、353、387、 434th, 469,516,522,526,533,535,539,549,550,682 etc.；

Under 10ppm dosage, have to the compound of the inhibiting rate of rice blast more than 90%：1、2、 3、10、11、16、 17th, 106,167,198,209,352,353,387,434,469,516 etc..And suppression of comparison medicament CK1, CK2 to rice blast Rate is 0；

Under 1ppm dosage, compound 1,2,10,16,17,167,209,352,353,434,469 etc. is to rice blast Inhibiting rate is still more than 70%, and comparison medicament Isoprothiolane inhibiting rate is 30% to the inhibiting rate of rice blast.

(2) to downy mildew bacterium [Peronospora manshurica (Naumov.) P.Sydow] in vitro antibacterial work Property test

Part of compounds to downy mildew bacterium [Peronospora manshurica (Naumov.) P. Sydow] Antifungal Activity in Vitro (represents) that test result is as follows with inhibiting rate：

Under 100ppm dosage, have to the compound of the inhibiting rate of downy mildew bacterium more than 90%： 25、26、31、 32nd, 47,55,56,62,70,71,77,85,86,92,100,102,107,115,116,121,122,155,156 etc..

Under 10ppm dosage, have to the compound of the inhibiting rate of downy mildew bacterium more than 90%： 25、32、47、 55th, 62,70,77,85,92,102,107,156 etc..

Under 1ppm dosage, compound 25,47,55,70,85,102,156 etc. still exists to the inhibiting rate of downy mildew bacterium More than 70%；And comparison medicament Bravo is 25% to the inhibiting rate of downy mildew bacterium.

Under 0.1ppm dosage, compound 25,55,85,102,156 etc. is to the inhibiting rate of downy mildew bacterium still 30% More than；And comparison medicament Bravo is only 5% to the inhibiting rate of downy mildew germ.

(3) the Antifungal Activity in Vitro of white rust of colza bacterium [Albugo candida (Pers.) Kuntze] is tested

The Antifungal Activity in Vitro to white rust of colza bacterium [Albugo candida (Pers.) Kuntze] of part of compounds (being represented with inhibiting rate) test result is as follows：

Under 100ppm dosage, have to the compound of the inhibiting rate of white rust of colza bacterium more than 90%： 333、335、 341、345、346、351、352、355、443、444、445、446、447、448、 503、504、505、538、539、540、541 Deng.

Under 10ppm dosage, have to the compound of the inhibiting rate of white rust of colza bacterium more than 90%： 335、341、 345th, 351,444,446,447,503,539,541 etc..

Under 1ppm dosage, compound 335,345,446,503,541 etc. still exists to the inhibiting rate of white rust of colza bacterium More than 70%；And comparison medicament Fluoxastrobin is 27% to the inhibiting rate of white rust of colza bacterium.

Under 0.1ppm dosage, compound 335, the inhibiting rate of 503,541 pairs of white rust of colza bacterium are still more than 40%； And comparison medicament Fluoxastrobin is only 7% to the inhibiting rate of white rust of colza bacterium.

(4) to the in vitro antibacterial of anthracnose of sorghum bacterium [Colletotrichum graminicola (Ces.) G.W.Wils.] Active testing

Part of compounds to anthracnose of sorghum bacterium [Colletotrichum graminicola (Ces.) G.W. Wils. Antifungal Activity in Vitro] (represents) that test result is as follows with inhibiting rate：

Under 100ppm dosage, have to the compound of the inhibiting rate of anthracnose of sorghum bacterium more than 90%： 4、9、18、19、 24th, 33,34,38,39,40,48,49,53,54,64,68,69,78,79,83,84 etc..

Under 10ppm dosage, have to the compound of the inhibiting rate of anthracnose of sorghum bacterium more than 90%：4、 19、33、38、 40th, 49,54,64,83,84 etc..

Under 1ppm dosage, compound 4,33,49,84 etc. is to the inhibiting rate of anthracnose of sorghum bacterium still more than 70%；And Comparison medicament thiram is 15% to the inhibiting rate of anthracnose of sorghum bacterium.

Under 0.1ppm dosage, the inhibiting rate of 4,49 pairs of anthracnose of sorghum bacterium of compound is still more than 35%；And comparison medicine Agent thiram is only 5% to the inhibiting rate of anthracnose of sorghum bacterium.

(5) to puccinia striiformis (Puccinia striiformis West f.sp.Tritici Eriks.Et Henn. Antifungal Activity in Vitro test)

Part of compounds to puccinia striiformis (Puccinia striiformis West f.sp.Tritici Eriks.Et Henn.) Antifungal Activity in Vitro (represent) that test result is as follows with inhibiting rate：

Under 100ppm dosage, have to the compound of the inhibiting rates of puccinia striiformis more than 90%： 361、362、 459th, 460,461,462,464 etc..

Under 10ppm dosage, have to the compound of the inhibiting rates of puccinia striiformis more than 90%： 361、459、 462nd, 464 etc..

Under 1ppm dosage, the grade of compound 462 is to the inhibiting rate of puccinia striiformis still more than 50%；And comparison medicament Tebuconazole is 5% to the inhibiting rate of puccinia striiformis.

Under 0.1ppm dosage, compound 462 is to the inhibiting rate of puccinia striiformis more than 25%；And comparison medicament penta Azoles alcohol is almost 0 to the inhibiting rate of puccinia striiformis.

(6) the Antifungal Activity in Vitro of rape Powdery Mildew (Erysiphe polygoni DC.) is tested

The Antifungal Activity in Vitro to rape Powdery Mildew (Erysiphe polygoni DC.) of part of compounds is (with suppression Rate processed represents) test result is as follows：

Under 100ppm dosage, have to the compound of the inhibiting rate of rape Powdery Mildew more than 90%： 333、351、 445th, 505,557 etc..

Under 10ppm dosage, have to the compound of the inhibiting rate of rape Powdery Mildew more than 90%： 333、445、557 Deng.

Under 1ppm dosage, the grade of compound 445 is to the inhibiting rate of rape Powdery Mildew still more than 50%；And comparison medicament Fluoxastrobin is 10% to the inhibiting rate of rape Powdery Mildew.

Under 0.1ppm dosage, compound 445 is 10% to the inhibiting rate of rape Powdery Mildew；Comparison medicament Fluoxastrobin pair The inhibiting rate of rape Powdery Mildew is almost 0.

(7) the Antifungal Activity in Vitro of wheat powdery mildew [Blumeria graminis (DC.) Speer] is tested

The Antifungal Activity in Vitro to wheat powdery mildew [Blumeria graminis (DC.) Speer] of part of compounds (being represented with inhibiting rate) test result is as follows：

Under 100ppm dosage, have to the compound of the inhibiting rate of wheat powdery mildew more than 90%： 361、362、 459th, 460,461,462,464,528,543 etc..

Under 10ppm dosage, have to the compound of the inhibiting rate of wheat powdery mildew more than 90%： 361、459、 462nd, 464,528,543 etc..

Under 1ppm dosage, compound 459,462,528,543 etc. to the inhibiting rate of wheat powdery mildew still 50% with On；And comparison medicament Tebuconazole is 15% to the inhibiting rate of wheat powdery mildew.

Under 0.1ppm dosage, the inhibiting rate of 462,543 pairs of wheat powdery mildews of compound is more than 30%；And comparison medicine Agent Tebuconazole is 5% to the inhibiting rate of wheat powdery mildew.

(8) the in vitro antibacterial work of Phytophthora infestans [Phytophthora infestans (Mont.) de Bary] Property test

The Phytophthora infestans [Phytophthora infestans (Mont.) de Bary] of part of compounds Antifungal Activity in Vitro (represents) that test result is as follows with inhibiting rate：

Under 100ppm dosage, the compound of the inhibiting rate of Phytophthora infestans more than 90% has：165、170、 180th, 210,211,213,225,226,227 etc..

Under 10ppm dosage, the compound of the inhibiting rate of Phytophthora infestans more than 90% has：165、180、 211st, 226 etc..

Under 1ppm dosage, the inhibiting rate of the Phytophthora infestans such as compound 211,226 is still in 50 more than %；And The inhibiting rate of comparison medicament cymoxanil Phytophthora infestans is 15%.

Under 0.1ppm dosage, the inhibiting rate of the Phytophthora infestans of compound 226 is more than 15%；And comparison medicament The inhibiting rate of cymoxanil Phytophthora infestans is 5%.

(9) to target bacterium [Alternaria solani (Ellis et Martin) Sorauer] in vitro suppression Bacterium active testing

Part of compounds to target bacterium [Alternaria solani (Ellis et Martin)

Sorauer] Antifungal Activity in Vitro (represent) that test result is as follows with inhibiting rate：

Under 100ppm dosage, have 333 to the compound of the inhibiting rate of target bacterium more than 90%, 351, 443rd, 445,504,505,557 etc..

Under 10ppm dosage, have to the compound of the inhibiting rate of target bacterium more than 90%： 351、445、 505 etc..

Under 1ppm dosage, compound 445 is to the inhibiting rate of target bacterium still more than 50%；And comparison medicament Fluoxastrobin is 7% to the inhibiting rate of target bacterium.

Under 0.1ppm dosage, the inhibiting rate of the Phytophthora infestans of compound 445 is more than 25%；And comparison medicament Fluoxastrobin is almost 0 to the inhibiting rate of target bacterium.

(10) the Antifungal Activity in Vitro of Ustilago maydis bacterium [Ustilago maydis (DC.) Corda] is tested

Part of compounds to the in vitro antibacterial work to Ustilago maydis bacterium [Ustilago maydis (DC.) Corda] Property (being represented with inhibiting rate) test result is as follows：

Under 100ppm dosage, have to the compound of the inhibiting rate of Ustilago maydis bacterium more than 90%：361、362、 364th, 459,460,461,462,464,491 etc..

Under 10ppm dosage, have to the compound of the inhibiting rate of Ustilago maydis bacterium more than 90%： 364、460、 462nd, 491 etc..

Under 1ppm dosage, compound 364,491 etc. is to the inhibiting rate of Ustilago maydis bacterium still in 50 more than %；And Comparison medicament Tebuconazole is 15% to the inhibiting rate of Ustilago maydis bacterium.

Under 0.1ppm dosage, compound 491 is to the inhibiting rate of Ustilago maydis bacterium more than 20%；And comparison medicament Tebuconazole is almost 0 to the inhibiting rate of Ustilago maydis bacterium.

(11) part of compounds (represents) that test result is as follows to the Antifungal Activity in Vitro of botrytis cinerea with inhibiting rate：

Under 100ppm dosage, have to the compound of the inhibiting rate of graw mold of tomato more than 90%：3、 8、16、23、 198th, 209,239,352,387,516,535,539,550,682,695,698,701,707 etc.；

Under 10ppm dosage, have to the compound of the inhibiting rate of graw mold of tomato more than 90%：198、 239、516、 682nd, 695,698,701,707 etc..And comparison medicament CK1, CK2 is 0 to the inhibiting rate of graw mold of tomato；

(12) part of compounds (represents) that test result is as follows to the Antifungal Activity in Vitro of bacterium of downy mildew of cucumber with inhibiting rate：

Under 100ppm dosage, have to the compound of the inhibiting rate of bacterium of downy mildew of cucumber more than 90%： 1、30、131、 387th, 522,676,678,682,707 etc.；

Under 10ppm dosage, have to the compound of the inhibiting rate of bacterium of downy mildew of cucumber more than 90%： 131、387、 676th, 682,707 etc..And comparison medicament CK1, CK2 is 0 to the inhibiting rate of bacterium of downy mildew of cucumber；

Under 1ppm dosage, compound 387,682,707 etc. is to the inhibiting rate of bacterium of downy mildew of cucumber still more than 70%；And Comparison medicament Bravo is 25% to the inhibiting rate of bacterium of downy mildew of cucumber.

2nd, insecticidal activity assay

A variety of insect pests of the compounds of this invention to plant have carried out insecticidal activity effect test.Insecticidal activity assay result is shown in Following embodiment.

Insecticidal activity assay：Method of testing is as follows, by the test compound sample solvent (species of solvent such as third being adapted to Ketone, methanol, DMSO etc., and selected according to its solvability to sample) dissolving, it is configured to required concentration prepare liquid.Examination Verification certificate member is made up of the interior small open container for having 12-15 days ages radish plants.By being placed on a piece of blade of test plant 30-40 bars are located at the insect (cutting leaf method) on a piece of blade cut from cultivated plant and contaminate the plant in advance. With leaf abscission, insect is moved on test plant.After contaminating in advance, the soil of test unit is covered with one layer of sand.

Method of testing is as follows：It will test in triplicate, and after the test-compound prepared is sprayed, make each test unit Dry 1 hour, black square is then placed on top.Make test unit in the growth room of 25 DEG C and 70% relative humidity Kept for 6 days.Then the worm death rate of each test unit of visual evaluation.

Conclusion (of pressure testing)

I is tested rice water weevil [Lissorhoptrus oryzophilus (Kuschel)] inhibiting rate

The inhibiting rate to rice water weevil [Lissorhoptrus oryzophilus (Kuschel)] of part of compounds is surveyed Test result is as follows：

Under 100ppm dosage, have to the compound of the inhibiting rate of rice water weevil more than 90%：36、 50、66、80、 81st, 96,112,187,270,298,326 etc..

Under 10ppm dosage, have to the compound of the inhibiting rate of rice water weevil more than 90%：36、 112、187、298、 326 etc..

Under 1ppm dosage, compound 112,187,298 etc. is to the inhibiting rate of Pyricularia oryzae still in 50 more than %；It is and right It is 10% to the inhibiting rate of rice water weevil according to medicament chlopyrifos.

Under 0.1ppm dosage, compound 112 is to the inhibiting rate of Pyricularia oryzae still more than 30%；And comparison medicament is poisoned with poison Tick is almost 0 to the inhibiting rate of rice water weevil.

Ii is tested the inhibiting rate of rice leafhopper [Maiestas oryzae (Matsumura)]

The inhibiting rate test result to rice leafhopper [Maiestas oryzae (Matsumura)] of part of compounds is as follows：

Under 100ppm dosage, have to the compound of the inhibiting rate of rice leafhopper more than 90%：142、 150、160、241、 257th, 275,289,322,343,392,427 etc..

Under 10ppm dosage, have to the compound of the inhibiting rate of rice leafhopper more than 90%：150、160、 241、257、 275th, 289 etc..

Under 1ppm dosage, compound 160,241,257 etc. is to the inhibiting rate of rice leafhopper still more than 50%；And comparison medicine Agent Bassa is 15% to the inhibiting rate of rice leafhopper.

Under 0.1ppm dosage, the inhibiting rate of 160,241 pairs of rice leafhoppers of compound is still more than 30%；And comparison medicament is secondary Fourth prestige is only 5% to the inhibiting rate of rice leafhopper.

Iii is tested the inhibiting rate of grain aphid [Sitobion miscanthi (Takahashi)]

The inhibiting rate test result to grain aphid [Sitobion miscanthi (Takahashi)] of part of compounds It is as follows：

Under 100ppm dosage, have to the compound of the inhibiting rate of grain aphid more than 90%：41、 42、57、58、 190th, 194,260,280,308,373,410 etc..

Under 10ppm dosage, have to the compound of the inhibiting rate of grain aphid more than 90%：58、190、 194、260、 280th, 308 etc..

Under 1ppm dosage, compound 190,194 etc. is to the inhibiting rate of grain aphid still more than 50%；And comparison medicament Imidacloprid is 17% to the inhibiting rate of grain aphid.

Under 0.1ppm dosage, the inhibiting rate of 190,194 pairs of grain aphids of compound is still more than 30%；And comparison medicament Imidacloprid is only 1% to the inhibiting rate of grain aphid.

Iv is tested the inhibiting rate of bollworm (Helicoverpa)

Part of compounds is as follows to the inhibiting rate test result of bollworm (Helicoverpa)：

Under 100ppm dosage, have to the compound of the inhibiting rate of bollworm more than 90%：402、 414、416、435、 467th, 475,493,481,511,531 etc..

Under 10ppm dosage, have 414,416,435,467 etc. to the compound of the inhibiting rate of bollworm more than 90%.

Under 1ppm dosage, compound 414,416,435,467 etc. is to the inhibiting rate of bollworm still in 50 more than %；And Comparison medicament gamma cyhalothrin is 25% to the inhibiting rate of bollworm.

Under 0.1ppm dosage, compound 467 is to the inhibiting rate of bollworm still more than 15%；And the efficient chlorine of comparison medicament Flucythrinate is only 1.5% to the inhibiting rate of bollworm.

V is tested the inhibiting rate of colorado potato bug [Leptinotarsa decemlineata (Say)]

Part of compounds to the survey of the inhibiting rate of colorado potato bug [Leptinotarsa decemlineata (Say)] Test result is as follows：

Under 100ppm dosage, have to the compound of the inhibiting rate of colorado potato bug more than 90%： 403、428、454、 465th, 484,501,560 etc..

Under 10ppm dosage, have to the compound of the inhibiting rate of colorado potato bug more than 90%：428、 454、465、 484th, 501 etc..

Under 1ppm dosage, compound 454,465 etc. is to the inhibiting rate of colorado potato bug still more than 40%；And comparison medicine Agent decis is 5% to the inhibiting rate of colorado potato bug.

Under 0.1ppm dosage, compound 465 is to the inhibiting rate of puccinia striiformis more than 25%；And comparison medicament bromine Cyano chrysanthemate is almost 0 to the inhibiting rate of colorado potato bug.

Vi is tested the inhibiting rate of pea weevil [Bruchus pisorum (L.)]

The inhibiting rate test result to pea weevil [Bruchus pisorum (L.)] of part of compounds is as follows：

Under 100ppm dosage, have to the compound of the inhibiting rate of pea weevil more than 90%：109、 110、111、112、 120th, 135,141,162,197 etc..

Under 10ppm dosage, have to the compound of the inhibiting rate of pea weevil more than 90%：110、111、 112、135、 141 etc..

Under 1ppm dosage, compound 111,112,135 etc. is to the inhibiting rate of pea weevil still more than 30%；And comparison medicine Agent effective cypermethrin is 5% to the inhibiting rate of pea weevil.

Under 0.1ppm dosage, compound 111,112,135 etc. is almost 0 to the inhibiting rate of pea weevil；Comparison medicament is phonetic Bacterium ester is almost 0 to the inhibiting rate of pea weevil.

Vii is tested the inhibiting rate of grub (Holotrichia parallela) (Holotrichia parallela Motschulsky)

Suppression of the part of compounds to grub (Holotrichia parallela) (Holotrichia parallela Motschulsky) Rate test result processed is as follows：

Under 100ppm dosage, have to the compound of the inhibiting rate of grub (Holotrichia parallela) more than 90%：123、 124th, 125,126,127,140,159 etc..

Under 10ppm dosage, have to compound of grub (Holotrichia parallela) inhibiting rate more than 90%：124、127、 140th, 159 etc..

Under 1ppm dosage, compound 127,159 etc. is to the inhibiting rate of grub (Holotrichia parallela) still more than 35%；And Comparison medicament imidacloprid is 5% to the inhibiting rate of grub (Holotrichia parallela).

Under 0.1ppm dosage, compound 159 is 15% to the inhibiting rate of grub (Holotrichia parallela)；And comparison medicament pyrrole Worm quinoline is almost 0 to the inhibiting rate of grub (Holotrichia parallela).

Viii is tested the inhibiting rate of haplothrips aculeatus [Haplothrips aculeatus (Fabricius)]

The inhibiting rate to haplothrips aculeatus [Haplothrips aculeatus (Fabricius)] of part of compounds is tested As a result it is as follows：

Under 100ppm dosage, have to the compound of the inhibiting rate of haplothrips aculeatus more than 90%：171、 174、192、 193rd, 201,229,237,244,263,295,301 etc..

Under 10ppm dosage, have to the compound of the inhibiting rate of haplothrips aculeatus more than 90%：171、 174、192、 201st, 229,237,244,295 etc..

Under 1ppm dosage, the inhibiting rate of the haplothrips aculeatus such as compound 192,201,229 is still more than 35%；And comparison medicine Agent chlopyrifos is 10% to the inhibiting rate of haplothrips aculeatus.

Under 0.1ppm dosage, compound 201 is to the inhibiting rate of haplothrips aculeatus more than 15%；And comparison medicament chlopyrifos Inhibiting rate to haplothrips aculeatus is 3.5%.

Ix is tested the inhibiting rate of corn borer (Ostrinia furnacalis)

Part of compounds is as follows to the inhibiting rate test result of corn borer (Ostrinia furnacalis)：

Under 100ppm dosage, have 252 to the compound of the inhibiting rate of corn borer more than 90%, 254,285,292, 297th, 310,359,389,396,497 etc..

Under 10ppm dosage, have to the compound of the inhibiting rate of corn borer more than 90%：252、285、 292、310、 359th, 389,497 etc..

Under 1ppm dosage, compound 310,359 etc. is to the inhibiting rate of corn borer still more than 30%；And comparison medicament is malicious Dead tick is 17% to the inhibiting rate of corn borer.

Under 0.1ppm dosage, compound 359 is to the inhibiting rate of corn borer more than 15%；And comparison medicament chlopyrifos pair The inhibiting rate of corn borer is almost 0.

X is tested the inhibiting rate of phthorimaea operculella [Phthorimaea operculella (Zeller)]

The inhibiting rate to phthorimaea operculella [Phthorimaea operculella (Zeller)] of part of compounds is surveyed Test result is as follows：

Under 100ppm dosage, have to the compound of the inhibiting rate of phthorimaea operculella more than 90%：206、209、 221st, 223,239,259,277,324,331 etc..

Under 10ppm dosage, have to the compound of the inhibiting rate of phthorimaea operculella more than 90%： 206、221、 223rd, 259,277,324 etc..

Under 1ppm dosage, compound 206,259,277,324 etc. to the inhibiting rate of phthorimaea operculella still 30% with On；And comparison medicament decis is 5% to the inhibiting rate of phthorimaea operculella.

Under 0.1ppm dosage, compound 259,277 etc. is to the inhibiting rate of phthorimaea operculella more than 5%；And compare Medicament decis is almost 0 to the inhibiting rate of phthorimaea operculella.

Xi part of compounds kills the test result of diamondback moth

Under 600ppm dosage, have to the compound of the fatal rate of diamondback moth more than 90%：1、76、 77、91、106、 224th, 300,344,576,596,629,676,678,683,684,686 etc.；

Under 100ppm dosage, have to the compound of the fatal rate of diamondback moth more than 90%：76、77、 91、224、 300th, 576,596,678,683 etc.；And comparison medicament CK1, CK2 is 0 to the fatal rate of diamondback moth.

Xii part of compounds kills the test result of black peach aphid

Under 600ppm dosage, have to the compound of the fatal rate of black peach aphid more than 90%：1、16、76、 77、91、300、 596th, 629,676,678,683,684,686 etc.；

Under 100ppm dosage, have to the compound of the fatal rate of black peach aphid more than 90%：76、77、 629、676、683 Deng；And comparison medicament CK1, CK2 is 0 to the fatal rate of black peach aphid.

Acaricidal activity determines

The compounds of this invention has carried out acaricidal activity effect test to the multiple mites insect of plant.Acaricidal activity measure knot Fruit sees following embodiment.

3rd, acaricidal activity determines

Method of testing is as follows：By test compound sample solvent (species of solvent such as acetone, methanol, the DMSO being adapted to Deng, and selected according to its solvability to sample) dissolving, it is configured to required concentration prepare liquid.Two-sided tape is cut into 2 ~3cm grow, be attached to one end of microslide, the scraps of paper on adhesive tape thrown off with tweezers, with No. zero writing brush select it is in the same size, It is female into mite that body colour is bright-coloured, action is active, and its back is bonded on two-sided tape and (paid attention to：Mite foot, mite palpus and mouth are not clung Device), every viscous 4 rows, often row is viscous 10.

Method of testing is as follows：It will test in triplicate, in temperature (25+1) DEG C, the biochemical culture of relative humidity 85% or so After placing 4h in case, with binocular vision, dead or torpescence individual is rejected.One end leaching with mite slide is into the liquid, gently Jog takes out after moving 5s, blots mite body and its decoction unnecessary around with blotting paper rapidly.It is placed in above-mentioned biochemical cultivation case, Binocular inspection result is used after 24h, mite body is touched with writing brush, using mite enough motionless person as death.The data obtained DPS statistical softwares Obtain virulence regression equation, LC₅₀With 95% confidence limit, coefficient correlation.

Conclusion (of pressure testing)

The inhibiting rate test of a Polyphagotarsonemus latus Banks (Polyphagotarsonemun latus)

The inhibiting rate test result of part of compounds Mite (Polyphagotarsonemun latus) is such as Under：

Under 100ppm dosage, the compound of the inhibiting rate of Mite more than 90% has 365,375, 381st, 386,395,400,408,412,418,430 etc..

Under 10ppm dosage, compound of the Mite rate more than 90% has：365、 381、395、 408th, 412,418,430 etc..

Under 1ppm dosage, the inhibiting rate of the Mite such as compound 395,408,412,418 still 50% with On；And the inhibiting rate of comparison medicament pyridaben Mite is 20%.

Under 0.1ppm dosage, the inhibiting rate of the Mite such as compound 408,412 is more than 25%；And compare The inhibiting rate of medicament pyridaben Mite is almost 0.

B surveys to the inhibiting rate of rice Schizotetranychus (Schizotetranychus yoshimekii Ehara et Wongsiri) Examination

Part of compounds is to rice Schizotetranychus (Schizotetranychus yoshimekii Ehara et Wongsiri) Inhibiting rate test result it is as follows：

Under 100ppm dosage, have to the compound of the inhibiting rates of rice Schizotetranychus more than 90%：419、425、432、 440th, 450,456,466,477,486 etc..

Under 10ppm dosage, have to the compound of the inhibiting rates of rice Schizotetranychus more than 90%：425、 432、440、 450th, 456 etc..

Under 1ppm dosage, compound 425,432,440,450,456 etc. to the inhibiting rates of rice Schizotetranychus still 50% with On；And comparison medicament pyridaben is 25% to the inhibiting rate of rice Schizotetranychus.

Under 0.1ppm dosage, compound 432,440 etc. is to the inhibiting rate of rice Schizotetranychus more than 25%；And comparison medicament Pyridaben is 5% to the inhibiting rate of rice Schizotetranychus.

C is tested the inhibiting rate of Jie-Li enzyme-SQ (Panonychus cirri)

Part of compounds is as follows to the inhibiting rate test result of Jie-Li enzyme-SQ (Panonychus cirri)：

Under 100ppm dosage, have to the compound of the inhibiting rate of Jie-Li enzyme-SQ more than 90%：507、 508、509、 513rd, 515,516,521,522,527 etc..

Under 10ppm dosage, have to the compound of the inhibiting rate of Jie-Li enzyme-SQ more than 90%：507、 509、513、 516th, 521,522 etc..

Under 1ppm dosage, compound 507,513,516,521 etc. is to the inhibiting rate of Jie-Li enzyme-SQ still more than 50%；And Comparison medicament pyridaben is 25% to the inhibiting rate of Jie-Li enzyme-SQ.

Under 0.1ppm dosage, the grade of compound 513 is to the inhibiting rate of Jie-Li enzyme-SQ more than 25%；The mite and comparison medicament is rattled away Spirit is 10% to the inhibiting rate of Jie-Li enzyme-SQ.

D is as follows to Tetranychus cinnabarinus part measurement result：

Under 600ppm dosage, have to the compound of the fatal rate of Tetranychus cinnabarinus more than 90%：8、 76、319、326、 535th, 576 etc.；

Under 100ppm dosage, have to the compound of the inhibiting rate of Tetranychus cinnabarinus more than 90%：8th, 319,535 etc..And Comparison medicament CK1, CK2 is 0 to the fatal rate of Tetranychus cinnabarinus.

Nematicidal Activity

The compounds of this invention has carried out eelworm-killing activity effect test to a variety of nematodes of plant.Nematicidal Activity knot Fruit sees following embodiment.

Nematicidal Activity

Method of testing is as follows：By test compound sample solvent (species of solvent such as acetone, methanol, the DMSO being adapted to Deng, and selected according to its solvability to sample) dissolving, it is configured to required concentration prepare liquid.Root knot is cleaned, is cut into The long segments of 1cm, are put into tissue mashing machine plus 3 times of water measured are smashed to pieces 30 seconds, are transferred to 200 mesh (75 μm of aperture) and 500 mesh (holes 26 μm of footpath) combination standard sieve, rinses plant tissue in sieve with running water, collects the line eggs in 500 mesh standard sieves, use quality Fraction is 0.5% NaClO surface sterilizations 3min, and sterile washing 3 times is standby.

1 filter paper is spread in 200 mesh standard sieves, root-knot nematode egg is placed on the filter paper in standard screen, it is put in In the basin for filling clear water, water is set just to soak filter paper, being placed in 25 DEG C of constant incubators makes larvae hatch, is spaced 24 hours and collects 2 instar larvaes in No. 1 basin, the larva after collection can be kept for 48 hours in 4 DEG C of cold storage refrigerators.

Method of testing is as follows：The ovum of collection is made into suspension (400 or so/mL) with clear water, pipetted with pipettor 0.5mL decoctions and 0.5mL ovum suspension are put in 2mL and counted in ware, are repeated 3 times, and 25 DEG C of constant temperature trainings are placed in after being mixed with fine glass rod Support in case, hatching number is checked after one week, calculate incubation rate and hatching inhibiting rate.

Hatch inhibiting rate=(control incubation rate-processing incubation rate)/control incubation rate × 100%

2 instar larvaes of collection are made into suspension (100 or so/mL) with clear water, with pipettor pipette 0.5mL decoctions and 0.5mL second instar larvae suspension is put in 2mL and counted in ware, is repeated 3 times, 25 DEG C of constant incubators are placed in after being mixed with fine glass rod In, dead, hot line borer population is checked after 48 hours.Inspection method：The decoction counted in ware is filtered out and only retains nematode, adds 2% chlorine Change sodium solution 1mL to be kept for 2 minutes, crimping or twist for dead worm, worm living for body rigidity, calculate the death rate and corrected mortality.

The death rate=verge of death borer population/processing nematode number × 100%

Corrected mortality=(the processing death rate-control death rate)/(100- compares the death rate) × 100%

Using DPS data processing softwares, calculating the virulence regression equation y=ax+b of various medicaments, (it is dead that y represents correction Die rate probit value, x represents the common logarithm of pharmacy quality concentration), the lethal concentration of 50 (LC₅₀) and suppress in concentration (IC₅₀)。

Conclusion (of pressure testing)

The inhibiting rate test of I bananas reniform nematode (Rotylenchus reniformis)

Part of compounds is as follows to the inhibiting rate test result of banana reniform nematode (Rotylenchus reniformis)：

Under 100ppm dosage, have 366 to the compound of the inhibiting rate of banana reniform nematode more than 90%, 369, 377th, 391,394,470,472,500,519,534 etc..

Under 10ppm dosage, compound of the Mite rate more than 90% has：369、 391、394、 472nd, 500,519 etc..

Under 1ppm dosage, the inhibiting rate of the Mite such as compound 391,394,472,500 still 40% with On；And comparison medicament carbofuran is 20% to the inhibiting rate of banana reniform nematode.

Under 0.1ppm dosage, compound 391,394 etc. is to the inhibiting rate of banana reniform nematode more than 25%；And compare Medicament carbofuran is 5% to the inhibiting rate of banana reniform nematode.

II is tested the inhibiting rate of rotten nematode (lesionnematode)

Part of compounds is as follows to the inhibiting rate test result of rotten nematode (lesionnematode)：

Under 100ppm dosage, have to the compound of the inhibiting rate of rotten nematode more than 90%：145、183、232、266、 287th, 306,317,544,549,555,561 etc..

Under 10ppm dosage, have to the compound of the inhibiting rate of rotten nematode more than 90%：145、183、232、266、 549th, 555,561 etc..

Under 1ppm dosage, compound 145,183,232,266,549 etc. is to the inhibiting rate of rotten nematode still more than 40%； And comparison medicament carbofuran is 15% to the inhibiting rate of rotten nematode.

Under 0.1ppm dosage, compound 183,232,266,549 etc. is to the inhibiting rate of rotten nematode in 25 more than %；And Comparison medicament carbofuran is 7% to the inhibiting rate of rotten nematode.

III is tested the inhibiting rate of corn SCN (Heterodera zeae)

Part of compounds is as follows to the inhibiting rate test result of corn SCN (Heterodera zeae)：

Under 100ppm dosage, have to the compound of the inhibiting rate of corn SCN more than 90%： 5、74、88、 114th, 152,185,256,273,304,337,536,552 etc..

Under 10ppm dosage, have to the compound of the inhibiting rate of corn SCN more than 90%：5、 74、88、 114th, 152,256,273,304,536,552 etc..

Under 1ppm dosage, the suppression to corn SCN such as compound 5,74,88,114,152,304,536,552 Rate is still more than 45%；And comparison medicament legendary god of farming pellet is 15% to the inhibiting rate of corn SCN.

Under 0.1ppm dosage, compound 88,114,152,304 etc. to the inhibiting rate of corn SCN 30% with On；And comparison medicament legendary god of farming pellet is 5% to the inhibiting rate of corn SCN.

Claims

A kind of 1. substituted benzo isothiazole compound, it is characterised in that the structure of substituted benzo isothiazole compound Formula is（I）It is shown：

（I）；

Wherein, R₁For cyano group, hydroxyl, C₁-C₄Alkyl, C₁-C₄Haloalkyl, C₃-C₆Cycloalkyl, C₃-C₄Alkenyl, cyano methyl, cyanogen Base ethyl, methoxyl group, ethyoxyl, acetyl group, trifluoroacetyl group, tribromo-acetyl base, C₁-C₄Alkoxy carbonyl, C₁-C₄Alkyl halide Epoxide carbonyl, trichloro-methylthio, trifluoromethyl sulphinyl base, methyl sulphonyl or ethylsulfonyl；

R₂It is independently selected from hydrogen, halogen, cyano group, methyl, methoxyl group, trifluoromethyl, trifluoromethoxy or difluoro-methoxy；n For 1,2,3 or 4；M is 1 or 2；

J be substitution thiazole, isothiazole or pyridine, building stone J-1, J-2, J-3 or J-4；

The J-1, J-2, J-3 or J-4 structural formula is respectively：

Wherein W, X, Y and Z are each independently N or CR₃, and in J-3 and J-4, one of W, X, Y or Z are N；

R₃For hydrogen, halogen, cyano group, C₁-C₄Alkyl, trifluoromethyl, difluoromethyl, methoxyl group, ethyoxyl, trifluoromethoxy, difluoro Methoxyl group, OCH₂CF₃Or OCHFCHF₂；Or formula（I）The salt of shown compound.
A kind of 2. substituted benzo isothiazole compound according to claim 1, it is characterised in that R₁For cyano group, hydroxyl Base, C₁-C₄Alkyl, cyclopropyl, cyano methyl, methoxyl group, ethyoxyl, acetyl group, trifluoroacetyl group, C₁-C₄Alkoxy carbonyl, Methyl sulphonyl or ethylsulfonyl.
A kind of 3. substituted benzo isothiazole compound according to claim 1, it is characterised in that：Formula（I）In, m For 1；Compound shown in logical formula (I) and hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methanesulfonic acid, to toluene sulphur The salt that acid, benzoic acid, phthalic acid, maleic acid, fumaric acid, sorbic acid, malic acid or citric acid are formed.
A kind of 4. substituted benzo isothiazole compound according to claim 3, it is characterised in that formula（I）Middle R₁For Cyano group, hydroxyl, C₁-C₄Alkyl, cyclopropyl, cyano methyl, methoxyl group, ethyoxyl, acetyl group, trifluoroacetyl group, C₁-C₄Alcoxyl Base carbonyl；

R₂It is independently selected from hydrogen, halogen, cyano group, methyl, methoxyl group, trifluoromethyl, trifluoromethoxy or difluoro-methoxy；

R₃For hydrogen, halogen, cyano group, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxyl group, trifluoromethoxy or difluoromethoxy Base.
5. a kind of substituted benzo isothiazole compound according to claim 2, it is characterised in that J is the thiophene of substitution Azoles, isothiazole or pyridine, the J-1, J-2, J-3 or J-4 structural formula is respectively：

In J-1 and J-2, one of X, Y or Z are N；In J-3 and J-4, one of W, X, Y or Z are N.
6. a kind of substituted benzo isothiazole compound according to claim 5, it is characterised in that J is the thiophene of substitution Azoles or pyridine, building stone J-1, J-2, J-3 or J-4；

The J-1, J-2, J-3 or J-4 structural formula is respectively：

In J-1, one of Y or Z are N；In J-3 and J-4, one of W, X, Y or Z are N.
A kind of 7. substituted benzo isothiazole compound according to claim 3, it is characterised in that formula（I）In, J For the chloro- 5- bases thiazoles of 2-, the chloro- 5- bases isothiazole of 3,4- bis- or the chloro- 5- yl pyridines of 2-；R₃For hydrogen or chlorine.
A kind of 8. substituted benzo isothiazole compound according to claim 3, it is characterised in that formula（I）In, R₁ For cyano group, methyl, ethyl, propyl group, isopropyl, normal-butyl, isobutyl group, cyclopropyl, cyano methyl, methoxyl group；R₂For hydrogen；N is 4。
A kind of 9. substituted benzo isothiazole compound according to claim 3, it is characterised in that

J is the chloro- 5- bases thiazoles of 2-, R₂For hydrogen, n=4, m=1.
10. use of the logical formula (I) compound or its salt in agricultural or other field in claim 1-7 described in any one On the way, it is characterised in that as preparing bactericide, insecticidal/acaricidal agent medicine.
A kind of 11. composition, it is characterised in that：Contain the logical formula (I) compound as defined in any one in claim 1-7 Or its salt is as active component；Wherein, the weight percentage of active component is 0.1-99% in composition.
12. purposes of the composition in agricultural or other field described in claim 9, it is characterised in that：For anti-pathogen, Insect evil mite.