CN102816135B - 5-methyl-1,2,3-thiadiazole-containing 1,3,4-thiadiazole derivatives and their preparation method and use - Google Patents

Abstract

The invention provides 5-methyl-1,2,3-thiadiazole-containing 1,3,4-thiadiazole derivatives and their preparation method and use. The 5-methyl-1,2,3-thiadiazole-containing 1,3,4-thiadiazole derivatives are 1,2,3-thiadiazole-containing heterocyclic compounds. Intermediates of the 5-methyl-1,2,3-thiadiazole-containing 1,3,4-thiadiazole derivatives and the 5-methyl-1,2,3-thiadiazole-containing 1,3,4-thiadiazole derivatives respectively have a general structural formula III and a general structural formula IV. The invention discloses the general structural formula and the preparation method of the 5-methyl-1,2,3-thiadiazole-containing 1,3,4-thiadiazole derivatives, and also discloses a use of the 5-methyl-1,2,3-thiadiazole-containing 1,3,4-thiadiazole derivatives as bactericides, plant virus resistance agents and plant activators. After being mixing with agriculture acceptable assistants or synergists, the 5-methyl-1,2,3-thiadiazole-containing 1,3,4-thiadiazole derivatives can be used for preparation of bactericides, plant virus resistance agents and plant activators. The invention also discloses a use of the 5-methyl-1,2,3-thiadiazole-containing 1,3,4-thiadiazole derivatives combined with commercial insecticides, bactericides, plant virus resistance agents and plant activators in prevention and treatment on agricultural, forest and gardening diseases, insect pests and viral diseases, and also discloses a preparation method thereof.

Description

One class 5-methyl isophthalic acid, 2,3-thiadiazoles connection-1,3-4-thiadiazoles derivative and its production and use

Technical field

Technical scheme of the present invention relates to containing 1,2-diazole compound, is specifically related to 5-methyl isophthalic acid, 2,3-thiadiazoles connection-1,3-4-thiadiazoles derivative.

Background technology

1,3-4-thiadiazoles, because contain N, S heteroatoms in heterocycle molecule simultaneously, can be simultaneously as participating in vital movement to body and acceptor, therefore show biological activity (Liu Hanwen widely, organic chemistry, 20012,32,1332.), particularly at pesticide field, more for example 1,3-4-thiadiazole compound is shown good desinsection, sterilization, weeding and plant growth regulating activity.No matter bis-heterocyclic compounds also becomes an important research direction at field of medicaments or at pesticide field.In same molecule, introduce two or more heterocyclic actives center, can change more flexibly the electronic structure feature of fractionated molecule, improve the biological activity of molecule, thereby it is better to obtain activity, the compound that using value is higher (Sun Yanrong, organic chemistry, 2008,28,151.).The synthesis strategy of two heterocycles mainly contains by two different heterocycle minor structure direct splicing together; On the basis of existing heterocycle one by one, utilize cyclization to synthesize another one heterocycle.Utilizing aroyl isorhodanate cyclization under acidic conditions is that the concrete method of classical way (Hassan, M.A.Arch.Pharm.Pharm.Med. Chem.1998 331,385.) of synthesizing 1,3-4-thiadiazoles has POCl ₃system, H ₂sO ₄/ ethanol system, H ₂sO ₄bodies etc. are compared with other cyclisation system, H ₂sO ₄/ CH ₃oH system has the advantages such as reaction conditions is gentleer, simple to operate, productive rate is higher, purification of products is convenient.1,2,3-thiadiazole compound has biological activity widely equally, relevant patent and document are summed up and are seen Bakulev, et al.Newyork:John Wiley & Sons, Inc, 2004 monograph, the research of relevant thiadiazoles mainly concentrates on 1,3,4-thiadiazoles derivative, 1,2,5-thiadiazoles derivative and 1, on 2,4-thiadiazoles derivative, and for 1, the research report of 2,3-thiadiazoles derivative activity is but relatively less.1,2,3-thiadiazoles derivative commercial kind in medicine and agricultural chemicals is few, agriculture field application

Only have cotton defoliant--disleave spirit (N-phenyl-N '-1,2,3-thiadiazoles-5-urea, TDZ), activating plants agent--Acibenzolar (phendioxin, 2,3-thiadiazoles-7-thiocarboxylic acid methyl esters, BTH), rice field sterilant--tiadinil (3 '-chloro-4,4 '-dimethyl-1,2,3-thiadiazoles-5-formylaniline, TDL).Contriver's research and design is in earlier stage synthesized and has found that first thiophene lures the inducing anti-disease activity of amine, at present just in industrialization development process.In order to find 1 of more high biological activities, 2,3-thiadiazole new compound, the present invention is 1,2, the outer pair keys of introducing of 3-Thiadiazole, a class 5-methyl isophthalic acid, 2 have been synthesized in design, 3-thiadiazoles connection-1,3-4-thiadiazoles derivative, and carried out the bioactive screening of system, to providing candidate compound for novel pesticide initiative research.

Summary of the invention

Technical problem to be solved by this invention is: new 5-methyl isophthalic acid is provided, 2,3-thiadiazoles connection-1, the synthetic method of 3-4-thiadiazoles derivative IV and intermediate III thereof, provide this compounds to suppress agricultural and gardening and forestry plant pathogen and antiviral biological activity and measuring method, the middle application of these compounds in agriculture field and gardening field and field of forestry is provided simultaneously.

The present invention solves this technical problem adopted technical scheme: the 5-methyl isophthalic acid with agriculture field, gardening field, field of forestry fungicidal activity, anti-phytoviral activity, inducing plant generation anti-disease activity, 2, the chemical structure of general formula of 3-thiadiazoles connection-1,3-4-thiadiazoles derivative IV and intermediate III thereof is shown in that formula is as follows:

Wherein, Ar is the group that is selected from phenyl, 4-fluorophenyl, 3-fluorophenyl, 2-nitrophenyl, 4-nitrophenyl, 3-chloro-phenyl-, 4-chloro-phenyl-, 4-aminomethyl phenyl, 3-aminomethyl phenyl, 3-p-methoxy-phenyl.

5-methyl isophthalic acid of the present invention, the synthetic method of 2,3-thiadiazoles connection-1,3-4-thiadiazoles derivative IV and intermediate III thereof is as follows:

Wherein, Ar is the group that is selected from phenyl, 4-fluorophenyl, 3-fluorophenyl, 2-nitrophenyl, 4-nitrophenyl, 3-chloro-phenyl-, 4-chloro-phenyl-, 4-aminomethyl phenyl, 3-aminomethyl phenyl, 3-p-methoxy-phenyl.

Specifically be divided into following steps:

A. the preparation of intermediate N (2-(5-methyl isophthalic acid, 2,3-thiadiazoles-4-formohydrazide group) sulfo-acyl group) substituted benzamide III:

By the 5-methyl isophthalic acid of 3.33 mmoles, the replacement isothiocyanic acid ester II of 2,3-thiadiazoles-4-formyl hydrazine I, 3.33 mmoles and 20 milliliters of DMF join in 50 milliliters of three mouthfuls of round-bottomed flasks, room temperature; Stir 6 hours.There is white solid, filter gained solid alcohol recrystallization, yield 60%-90%, measure fusing point and ¹h NMR, the amount of synthetic compound III expands or dwindles by corresponding proportion, and the volume of reaction vessel expands or dwindles by corresponding proportion; The chemical structure of compound III and physical and chemical parameter are in Table 1.

B.5-methyl isophthalic acid, the preparation of 2,3-thiadiazoles connection-1,3-4-thiadiazoles IV:

N-(2-(5-methyl isophthalic acid, 2,3-thiadiazoles-4-formohydrazide group) sulfo-acyl group) the substituted benzamide III, 20 methyl alcohol, the 0.1 milliliter of vitriol oil that in 50 milliliters of original place flasks, add 3.0 mmoles, stirring and refluxing 6 hours.There is white solid, filter gained solid alcohol recrystallization, yield 60%-90%, measure fusing point and ¹h NMR, the amount of synthetic compound IV expands or dwindles by corresponding proportion, and the volume of reaction vessel expands or dwindles by corresponding proportion; The chemical structure of compound IV and physical and chemical parameter are in Table 1.

C.5-methyl isophthalic acid, 2,3-thiadiazoles connection-1,3-4-thiadiazoles derivative IV and the mensuration of intermediate III to pathogenic fungi growth activity thereof:

5-methyl isophthalic acid of the present invention, 2, 3-thiadiazoles connection-1, 3-4-thiadiazoles derivative IV and intermediate III sterilization thereof or bacteriostatic activity adopt thalli growth rate assay method, detailed process is: get 5 milligrams of sample dissolution in appropriate dimethyl formamide, then with containing the medicament that a certain amount of polysorbas20 emulsifier aqueous solution is diluted to 500 mcg/ml, reagent agent is respectively drawn under aseptic condition in 1 milliliter of injection culture dish, add respectively again 9 milliliters of substratum, after shaking up, make 50 mcg/ml pastilles dull and stereotyped, to add the flat board of 1 milliliter of aqua sterilisa, do blank, with the punch tool of 4 millimeters of diameters, along mycelia outer rim, cut bacterium dish, move on pastille flat board, being equilateral triangle puts, every processing repeats 3 times, culture dish is placed in 24 ± 1 degrees Celsius of constant incubators and is cultivated, colony diameter to be contrasted expands to 2-3 centimetre of " Invest, Then Investigate " and respectively processes bacterium dish expansion diameter, average, relatively calculate relative bacteriostasis rate with blank, the kind that comprises multiple representative majority of plant pathogenic bacteria of the actual generation in field in China's agriculture production for examination bacterial classification, its title and code name comprise AS: tomato early blight bacterium (Alternaria solani), BC: botrytis cinerea pers (Botrytis cinerea), CA: peanut Cercospora bacteria (Cercospora arachidicola), GZ: fusarium graminearum (Gibberella zeae), PI: phytophthora infestans (Phytophthora infestans (Mont.) de Bary), PP: Botryosphaeria berengeriana f. sp (Physalosporapiricola), PS: Rhizoctonia solani Kuhn (Pellicularia sasakii), RC: Rhizoctonia cerealis (Rhizoctonia cerealis), SS: Sclerotinia sclerotiorum (Sclerotinia sclerotiorum).

D. 5-methyl isophthalic acid of the present invention, the mensuration of 2,3-thiadiazoles connection-1,3-4-thiadiazoles derivative IV and intermediate III inducing anti-disease activity thereof:

5-methyl isophthalic acid of the present invention, the screening method of 2,3-thiadiazoles connection-1,3-4-thiadiazoles derivative IV and intermediate III evoking tobacco resisting tobacco mosaic virus (TMV) activity thereof is as follows: the mensuration of in vitro directly antiviral activity adopts half page of method to carry out, live body induction is by the consistent common cigarette of seedling age, 3 basins are one group, cigarette seedling respectively at inoculation pre-treatment in first 7 days, processing mode comprises: spray test compound solution 2 to 3 times, each 10 milliliters, or soil treatment, each 10 milliliters, the 7th day frictional inoculation TMV on the tobacco leaf newly growing, cigarette seedling is placed under its growth optimal temperature and illumination and is cultivated after 3 days, check incidence, comprehensive scab number is calculated as follows out the inducing anti-disease toxic effect fruit of test compound to TMV, 3 repetitions are established in each processing, 2 kinds of contrast minute blank and the contrasts of standard chemicals treatment, selecting tiadinil (TDL) (purity is greater than 99.5%) is the induced resistance of plant activiator of standard:

$R=\frac{\mathrm{CK}-I}{\mathrm{CK}}\×100$

Wherein, R is the induction effect of new compound to Resistance In Tobacco TMV, unit: %

CK is the average withered spot number of clear water contrast blade, unit: individual

I processes the average withered spot number of rear blade, unit: individual through compound induction;

The invention has the beneficial effects as follows: the present invention is to 5-methyl isophthalic acid, 2,3-thiadiazoles connection-1,3-4-thiadiazoles derivative IV and intermediate III thereof have been carried out guide's optimization, and synthetic new compound has been carried out the screening of bacteriostatic activity and antiviral activity and mixed the research of using, this compounds can be for control agriculture field and field of forestry and the Plant diseases in gardening field and the control of virus disease.

The present invention illustrates 5-methyl isophthalic acid more by specific preparation and biological activity determination embodiment, 2,3-thiadiazoles connection-1, synthetic and biological activity and the application thereof of 3-4-thiadiazoles derivative IV and intermediate III thereof, described embodiment is unrestricted the present invention for illustrating the present invention only, especially its biological activity only illustrates, and unrestricted this patent, embodiment is as follows:

Embodiment 1

The preparation of intermediate N (2-(5-methyl isophthalic acid, 2,3-thiadiazoles-4-formohydrazide group) sulfo-acyl group) substituted benzamide III:

By the 5-methyl isophthalic acid of 3.33 mmoles, the replacement isothiocyanic acid ester II of 2,3-thiadiazoles-4-formyl hydrazine I, 3.33 mmoles and 20 milliliters of DMF join in 50 milliliters of three mouthfuls of round-bottomed flasks, room temperature; Stir 6 hours.There is white solid, filter gained solid alcohol recrystallization, yield 60%-90%, measure fusing point and ¹h NMR, the chemical structure of compound III and physical and chemical parameter are in Table 1.

Embodiment 2

5-methyl isophthalic acid, the preparation of 2,3-thiadiazoles connection-1,3-4-thiadiazoles IV:

N-(2-(5-methyl isophthalic acid, 2,3-thiadiazoles-4-formohydrazide group) sulfo-acyl group) the substituted benzamide III, 20 methyl alcohol, the 0.1 milliliter of vitriol oil that in 50 milliliters of original place flasks, add 3.0 mmoles, stirring and refluxing 6 hours.There is white solid, filter gained solid alcohol recrystallization, yield 60%-90%, measure fusing point and ¹h NMR, the chemical structure of compound IV and physical and chemical parameter are in Table 1.

Embodiment 3

5-methyl isophthalic acid of the present invention, the antibacterial or fungicidal activity of 2,3-thiadiazoles connection-1,3-4-thiadiazoles derivative IV and intermediate III thereof:

Title and the code name of the frequently seen plants pathogenic fungi of the present invention's test comprise AS: tomato early blight bacterium (Alternaria solani); BC: botrytis cinerea pers (Botrytis cinerea); CA: peanut Cercospora bacteria (Cercospora arachidicola); GZ: fusarium graminearum (Gibberella zeae); PI: phytophthora infestans (Phytophthora infestans (Mont.) de Bary); PP: Botryosphaeria berengeriana f. sp (Physalospora piricola); PS: Rhizoctonia solani Kuhn (Pellicularia sasakii); RC: Rhizoctonia cerealis (Rhizoctonia cerealis); SS: Sclerotinia sclerotiorum (Sclerotinia sclerotiorum), these bacterial classifications have good representativeness, can represent the kind of most of pathogenic bacteria that in agriculture production, field occurs.Thalli growth rate method measurement result is in Table 2, and table 2 shows, when 50 mcg/ml, all compounds that the present invention synthesizes all have fungicidal activity in various degree, TN-TDZ9, TN-TDZ10 to the fungicidal activity of AS higher than 40%; TN-TDZi1, TN-TDZi7, TN-TDZi9, TN-TDZ9 to the fungicidal activity of CA higher than 40%; TN-TDZi3, TN-TDZ6, TN-TDZi9, TN-TDZi9 to the fungicidal activity of GZ higher than 40%; TN-TDZi1, TN-TDZ1, TN-TDZi2, TN-TDZ2, TN-TDZ3, TN-TDZi4, TN-TDZ4, TN-TDZi5, TN-TDZ5, TN-TDZi6, TN-TDZi7, TN-TDZ7, TN-TDZi8, TN-TDZi9, TN-TDZ9, TN-TDZi10 to the fungicidal activity of PP higher than 40%; TN-TDZi3, TN-TDZ6, TN-TDZi9, TN-TDZi9 to the fungicidal activity of GZ higher than 40%; TN-TDZi1, TN-TDZi3, TN-TDZ3, TN-TDZ4, TN-TDZ5, TN-TDZi7, TN-TDZ9 to the fungicidal activity of BC higher than 40%; TN-TD4, TN-TDZi6, TN-TDZ6, TN-TDZi9, TN-TDZ9, TN-TDZi10 to the fungicidal activity of SS higher than 40%; TN-TDZ4, TN-TDZ5, TN-TDZ6, TN-TDZ10 to the fungicidal activity of PI higher than 40%; TN-TD4, TN-TDZi6, TN-TDZ6, TN-TDZi9, TN-TDZ9, TN-TDZi10 to the fungicidal activity of SS higher than 40%; Except individual compound TN-TDZi4, TN-TDZ8, majority of compounds is all greater than 40% to the fungicidal activity of RC; Except individual compound TN-TDZi2, TN-TDZ4, TN-Tdi4 majority of compounds are all greater than 40% to the fungicidal activity of PS.Therefore, this compounds has shown good fungicidal activity.

Embodiment 4

5-methyl isophthalic acid of the present invention, the effect of 2,3-thiadiazoles connection-1,3-4-thiadiazoles derivative IV and the anti-Resistance In Tobacco tobacco mosaic virus (TMV) of intermediate III thereof:

The measurement result of anti-TMV activity is in Table 3, table 3 shows, commercial Genes For Plant Tolerance tobacco mosaic disease toxicant virazole has certain activity to TMV, most of 5-methyl isophthalic acid of the present invention, 2,3-thiadiazoles connection-1,3-4-thiadiazoles derivative IV and intermediate III thereof have the activity of good anti-TMV, and TN-TDZi1, TN-TDZ1, TN-TDZi2, TN-TDZ6, TN-TDZi7, TN-TDZ8, TN-TDZ9, the TN-TDZi10 passivation effect when 100 mcg/ml are all significantly higher than contrast medicament virazole under same concentrations and the result for the treatment of of Ningnanmycin.TN-TDZi1, TN-TDZ1, TN-TDZi3, TN-TDZi5, the result for the treatment of of TN-TDZ8 when 100 mcg/ml are all significantly higher than contrast medicament virazole under same concentrations and the passivation effect of Ningnanmycin.TN-TDZ1, TN-TDZ4, the TN-TDZ8 induction effect when 100 mcg/ml is all significantly higher than the induction effect of the contrast medicament tiadinil TDL under same concentrations.

Embodiment 5

5-methyl isophthalic acid of the present invention, the application in 2,3-thiadiazoles connection-1,3-4-thiadiazoles derivative IV and intermediate III thereof and insecticide composition control agricultural and forestry and gardening plant insect pest

All 5-methyl isophthalic acids of the present invention, 2,3-thiadiazoles connection-1,3-4-thiadiazoles derivative IV and intermediate III and existing sterilant: Chlorpyrifos 94, the sub-Nong in ground, acetamiprid, Affirm (Merck Co.), milbemectin, Avrmectin, pleocidin, fenvalerate, efficient fenvalerate, Cypermethrin, effective cypermethrin, lambda-cyhalothrin, Deltamethrin, Fenvalerate, Beta-cyfloxylate, cyfloxylate, Lambda-lambda-cyhalothrin, Permanone, permethrin, esbiothrin, cyhalothrin, bifenthrin, permethrin, ether chrysanthemum ester, flumethrin, fluvalinate, Provado, acetamiprid, Ti304, imidaclothiz, thiacloprid, Diacloden, clothianidin, MTI-446, clothianadin, Da Tenan, diflubenzuron, young urea goes out, Teflubenzuron, deinsectization is grand, HEXAFLUMURON, flufenoxuron, pyridine worm is grand, lufenuron, poisonous insect urea, penfluron, Noviflumuron is noviflumuron, and it is for No. CAS 121451-02-3, flucycloxuron, Novaluron is Rimon, fluorine pyridine urea, Bay sir 6874 i.e. { 1-[(3.5-bis-chloro-4) 4-nitrophenoxy phenyl 3-3-(2-chlorobenzene)-urea }, Bay SIR-8514 i.e. [1-(4-Trifluoromethoxyphen-l)-3-(2-chlorobenzene)-urea], piperazine worm urea, Bistrifluron is bistrifluron, furan tebufenozide, worm hydrazides, chlorine worm hydrazides, methoxyfenozide, ring worm hydrazides, Rogor, omethoate, SD-1750, acephate, triazophos, Resitox, pyridaphenthione, isazofos, Ro 7-5050, SevinCarbaryl, Aphox, meta-tolyl-N-methylcarbamate (MTMC), isoprocarb, cartap, fenobucarb, leaf disperses, carbaryl, benfuracarb, carbosulfan, cartap, bromopropylate, hexythiazox, fenpyroximate, pyridaben, clofentezine, propargite, diafenthiuron, benfuracarb, pymetrozine, spiral shell mite ester, spiral shell worm ester, spiral shell worm ethyl ester, butene-fipronil, azocyclotin, Buprofezin, ethoprophos, ethiprole, desinsection list, disosultap, chlorantraniliprole, Flubendiamide, fluorine cyanogen insect amide, cyanogen insect amide, Tolfenpyrad, tebufenpyrad, bromothalonil, pyrazinones, second mite azoles, tebufenpyrad, the young ketone of rattling away, Nylar, any one in emaricin etc. or two kinds are used in combination, 5-methyl isophthalic acid of the present invention, 2,3-thiadiazoles connection-1,3-4-thiadiazoles derivative IV and intermediate III thereof the quality percentage composition in composition is 1%-90%, 5-methyl isophthalic acid of the present invention, the ratio of 2,3-thiadiazoles connection-1,3-4-thiadiazoles derivative IV and intermediate III and commercially available agricultural chemical is mass percent 1%: 99% to 99%: 1%, can directly be watered rear spraying, comprise the upper acceptable solvent of agricultural and emulsifying agent and solubility promoter and synergistic agent etc. in its preparation, the formulation of composition processing is selected from wettable powder, sustained release dosage, pulvis, micro-capsule suspension, dispersible body preparation, dispersible solid preparation, seed treatment emulsion, aqueous emulsion, large granula, granule, microemulsion, oil-suspending agent, finish, seed with coated pesticidal, suspended emulsion agent, water-soluble granule, soluble thick agent, water-dispersible granules, poison grain, aerosol, block poison bait, sustained-release block, dense poison bait, CG/Encapsulated granule, capsule suspension, dispersible dense dose, pulvis, Waterless Seed Dressing pulvis, missible oil, electrostatic spray agent, water-in-oil emulsion, seed treatment agent, oil-in-water emulsion, smoke candle, granula subtilis, smoke candle, smoke cartridge, smog rod, seed treatment suspension agent, smog sheet, smoke substance, smog ball, granular poison bait, foaming agent, large granula, drift pulvis, granula, ointment, thermal fog, solid-liquid mixes dress agent, liquid/liquid mixes dress agent, cold mist agent, Gu Gu/mix filling agent, medicine paint, seed treatment liquor, microgranules, oil suspending agent, finish, oil-dispersing property pulvis, paste, sheet poison bait, dense jelly, sprinkle and water agent, stylus, seed coat agent, poison bait, basting agent, fritter poison bait, suspension agent, suspension emulsion, water-soluble granule, soluble thick agent, film forming finish, soluble powder, seed treatment water solube powder, ultra-low volume suspension agent, tablet, follow the trail of pulvis, ultra low volume liquids, steam releasing agent, water-dispersible granules, wettable powder, any one in wet-mixing kind water-dispersible powder, the insect pest that can prevent and treat mainly contains red spider, Asiatic migrotory locust, clouding car locust, Chinese rice grasshopper, Patanga japonica (l.Bol.), single thorn mole cricket, east mole cricket, rice thrips, onion thrips, greenhouse thrips, haplothrips aculeatus, Mai Jian manages thrips, Trialeurodes vaporariorum Westwood, Bemisia tabaci, rice green leafhopper, green leaf hopper, chlorita biguttula, spot clothing plant hopper, brown paddy plant hopper, white backed planthopper, small brown rice planthopper, the flat angle of sugarcane plant hopper, cotten aphid, green bugs, grain aphid, black peach aphid, kaoliang aphid, radish aphid, icerya purchasi, Pseudaulacaspis pentagona, unaspis shield kuwana, san jose scale, wax insect, ceroplastes rubens, Didesmococcus koreanus Borchs, pear lace bug, banana lace bug, thin corner piece stinkbug, Orius minutus, slender rice bug, paddy fly, niphe elongata, scotinophora lurida, Nezara viridula smaragdula Fabricius., green plant bug, alfalfa plant bug, black striped plant bug, chrysopa septempunctata, beautiful Chrysopa, Chinese green lacewing, rain moth, casemaking clothes moth, cnidocampa flavescens walker, brown slug moth, thosea siensis, gelechiid, pink bollworm, brachmia triannuella, small cabbage moth, small heart-eating peach worm, eating-core bean worm, small heart-eating peach worm, apple Spilonota lechriaspis, brown belt length leaf roller, Adoxophyes cyrtosema, striped rice borer, bean-pod borer, Pyrausta nubilalis (Hubern)., yellow rice borer, Oeobia undalis, Cnaphalocrocis medinali(rice leaf roller), bar snout moth's larva, the wild snout moth's larva of lap leaf, dichocrocis punctiferalis, armyworm, prodenia litura, rice green caterpillar, anomis flava, beet armyworm, pink rice borer, bollworm, ancient cooking vessel point diamond drill, black cutworm, large cutworm, yellow cutworm, steal poison moth, gypsymoth, palaearctic sweet potato, greenish brown hawk moth, straight burr rice hesperiidae, pelopidas mathias, oranges and tangerines swallowtail butterfly, Common Mormon, small white, pyrameis indica, the yellow a kind of butterfly harmful to crop plants of ramie, beans blister beetle, Venus ground beetle, wrinkle sheath ground beetle, wheat head ground beetle, pleonomus canaliculatus, Agriotes subrittatus Motschulsky, khapra beetle, attagenus piceus, the little buprestid beetle of oranges and tangerines, gold edge buprestid beetle, tenebrio molitor, dark mealworm, red flour beetle, confused flour beetle, verdigris different beetle, H. parallela, holotrichia oblita, mulberry borer, longicorn beetle, nadezhdiella cantori, pink neck longicorn, large daikon leaf beetle, daicon leaf beetle, aulacophora femoralis, Phyllotreta striolata, Callosobruchus chinensis, pea weevil, broad bean weevil, sitophilus zea-mais, rice weevil, dolerus tritici, pear fruit sawfly, yellowish leukorrhea ichneumon wasp, armyworm white star ichneumon wasp, corn earworm is hanged cocoon ichneumon wasp, bollworm tooth lip ichneumon wasp, snout moth's larva stain wart ichneumon wasp, mosquito, fly, horsefly, wheat midge, contarinia tritici, pachydiplosis oryzae, citrus fruit fly, melon trypetid, the latent fly of wheat leaf ash, Americal rice leaf miner, the black latent fly of beans stalk, frit fly, plant fly, onion fly, radish fly, full skirt chases after posts fly, Pyrausta nubilalis (Hubern). is strict posts fly, armyworm lacks must post the Agricultural pests such as fly, forestry pest, gardening pest insect and sanitary insect pest, controlling mode also comprises double controlling simultaneously, the prevention effect of composition is good, and drug effect plays stably, and has certain synergism and summation action, does not find not have the composition of antagonistic action, the applicable crop of these compositions comprises paddy, wheat, barley, oat, corn, Chinese sorghum, sweet potato, potato, cassava, soybean, pea-pods, broad bean, pea, mung bean, red bean, cotton, silkworm and mulberry, peanut, rape, sesame, Sunflower Receptacle, beet, sugarcane, coffee, cocoa, ginseng, the bulb of fritillary, rubber, coconut, oil palm, sisal hemp, tobacco, tomato, capsicum, radish, cucumber, Chinese cabbage, celery, hot pickled mustard tube, beet, rape, green onion, garlic, watermelon, muskmelon, hami melon, pawpaw, really, tea, wild vegetable, bamboo shoots, hops, potato, paddy rice, pepper, apple, banana, citrus, peach, papaya, orchid, potted landscape.Composition has improved the defence capability of plant in desinsection, makes plant produce the defence capability to pathogenic fungi, bacterium and virus infection.

Embodiment 6

5-methyl isophthalic acid of the present invention, the application in 2,3-thiadiazoles connection-1,3-4-thiadiazoles derivative IV and intermediate III thereof and sterilant combination control agricultural and forestry and gardening plant disease

All 5-methyl isophthalic acids of the present invention, 2,3-thiadiazoles connection-1,3-4-thiadiazoles derivative IV and intermediate III thereof and existing sterilant are as diazosulfide, tiadinil, tisocromide, first thiophene lures amine, 4-methyl isophthalic acid, 2,3-thiadiazoles-5-formic acid, 4-methyl isophthalic acid, 2,3-thiadiazoles-5-sodium formiate, 4-methyl isophthalic acid, 2,3-thiadiazoles-5-ethyl formate, DL-beta-aminobutyric acid, isotianil (isotianil), virazole, antofine, Ningnanmycin or Whitfield's ointment, frost urea cyanogen, thiram, ziram, zinc manganese ethylenebisdithiocarbamate, phosethyl Al, thiophanate_methyl, m-tetrachlorophthalodinitrile, enemy can be loose, procymidone, fenpropidin, thiophanate methyl, thiophanate, Metalaxyl-M, Whitfield's ointment, flumorph, dimethomorph, efficient metaxanin, efficient M 9834, two chlorine zarilamids, flusulfamide, first flusulfamide, thiophene fluorine bacterium amine, fultolanil, tecloftalam, ring propionyl bacterium amine, cyflufenamid, fenhexamid, zarilamid, Silthiopham, furametpyr, pyrrole metsulfovax, mandipropamid, zoxamide, fenfuram, carboxin, chlozolinate, RP-26019, Azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, SSF 126, orysastrobin, ZEN 90160, Strobilurin, oxime bacterium ester, enostroburin, alkene oxime amine, oxygen ring azoles, bromuconazole, SN-108266, difenoconazole, alkene azoles alcohol, efficient alkene azoles alcohol, epoxiconazole, RH-7592, fluquinconazole, fluzilazol, flutriafol, own azoles alcohol, imibenconazole, plant bacterium azoles, metconazole, nitrile bacterium azoles, Topaze, Wocosin 50TK, prothioconazoles, simeconazoles, tebuconazole, tertraconazole, triadimenol, triticonazole, bitertanol, thiabendazole, fuberidazole, imazalil, efficient imazalil, prochloraz, fluorine bacterium azoles, cyazofamid, fenamidone, Evil imidazoles, pefurazoate, famoxadone, SYP-Z048, hymexazo, the spirit of Evil frost, Guardian, etridiazole, octhilinone, benthiozole, dodemorph, fenpropimorph, tridemorph, fenpiclonil, fludioxonil, fluazinam, pyrifenox, ring pyridine bacterium amine, boscalid amine, fluopicolide, pyridine bacterium amine, cyprodinil, fluorine mepanipyrim, ferimzone, mepanipyrim, phonetic mould amine, fenarimol, nuarimol, chinomethionate, dithianon, ethoxyquin, hydroxyquinoline, the third oxygen quinoline, benzene oxygen quinoline, the mould prestige of second, iprovalicarb, benzene metsulfovax, Propamocarb, methasulfocarb, edifenphos, iprobenfos, pyrazophos, tolclofosmethyl, miewensu, kasugamycin, polyoxin, Polyoxin, validamycin, jingganmycin, Streptomycin sulphate, metaxanin, furalaxyl, M 9834, ofurace, mebenil, derosal, F-1991, thiophanate_methyl, triazolone, bupirimate, dimethirimol, the phonetic phenol of second, Difolatan, Vancide 89, Phaltan, Vinclozoline, fluoromide, dimetachlone, m-tetrachlorophthalodinitrile, isoprothiolane, Kitazine, bismerthiazol, quintozene, zinc manganese ethylenebisdithiocarbamate, zinc 1,2-propylene bisdithiocarbamate, fosetylaluminium, sulphur, Bordeaux mixture, copper sulfate, copper oxychloride, Red copper oxide, copper hydroxide, metrafenone, pencycuron, diclomezin, phthalide, pyroquilon, volution bacterium amine, tricyclazole, triforine, the pyridine of many fruits, the pungent salt of biguanides, iminoctadine, dicloran, benzene flusulfamide, toluene flusulfamide, K-281, fenaminosulf, oxolinic acide, probenazole, bronopol, methyl iodide, metamsodium, enemy's line ester, dazomet, dichloroisopropyl ether, lythidathion, cadusafos, fensulfothion, thionazin, fenamiphos, ethoprophos, dichlofenthion, isazofos, fosthietan, oxamyl, aldicarb, carbofuran, sulfuryl fluoride, dichloropropylene, dichloro-isonicotinic acid, other known any any one or two kinds that can be used as in sterilant such as allyl isothiazole are used in combination, 5-methyl isophthalic acid of the present invention, 2,3-thiadiazoles connection-1,3-4-thiadiazoles derivative IV and intermediate III thereof the total quality percentage composition in composition is 1%-90%, 5-methyl isophthalic acid of the present invention, the ratio of 2,3-thiadiazoles connection-1,3-4-thiadiazoles derivative IV and intermediate III and commercially available agricultural chemical is mass percent 1%: 99% to 99%: 1%, the prevention effect of composition is good, and these compositions have certain synergism and summation action, does not find to have the composition of antagonistic action, above-mentioned composition can be for the control of agricultural plants disease and gardening plant disease, controlling object comprises that more than 20 of the Achylas, Aphanomyces, pythium, phytophthora, Sclerospora, Plasmopara, Pseudoperonospora, Peronospora of Oomycete etc. belong to the diseases that produce, as other diseases of plurality of cereals crop, cash crop, gardening plant and the forestry plants such as seedling blight of rice, tomato root maize ear rot, the late blight of potato, black shank, millet Powdery Mildew, downy mildew of garpe, downy mildew of lettuce, cucumber downy mildew, cucumber anthracnose etc., the formulation of composition processing is selected from wettable powder, sustained release dosage, pulvis, micro-capsule suspension, dispersible body preparation, dispersible solid preparation, seed treatment emulsion, aqueous emulsion, large granula, granule, microemulsion, oil-suspending agent, finish, seed with coated pesticidal, suspended emulsion agent, water-soluble granule, soluble thick agent, water-dispersible granules, poison grain, aerosol, block poison bait, sustained-release block, dense poison bait, CG/Encapsulated granule, capsule suspension, dispersible dense dose, pulvis, Waterless Seed Dressing pulvis, missible oil, electrostatic spray agent, water-in-oil emulsion, seed treatment agent, oil-in-water emulsion, smoke candle, granula subtilis, smoke candle, smoke cartridge, smog rod, seed treatment suspension agent, smog sheet, smoke substance, smog ball, granular poison bait, foaming agent, large granula, drift pulvis, granula, ointment, thermal fog, solid-liquid mixes dress agent, liquid/liquid mixes dress agent, cold mist agent, Gu Gu/mix filling agent, medicine paint, seed treatment liquor, microgranules, oil suspending agent, finish, oil-dispersing property pulvis, paste, sheet poison bait, dense jelly, sprinkle and water agent, stylus, seed coat agent, poison bait, basting agent, fritter poison bait, suspension agent, suspension emulsion, water-soluble granule, soluble thick agent, film forming finish, soluble powder, seed treatment water solube powder, ultra-low volume suspension agent, tablet, follow the trail of pulvis, ultra low volume liquids, steam releasing agent, water-dispersible granules, wettable powder, any one in wet-mixing kind water-dispersible powder.The applicable crop of these compositions comprises that cereal (comprises paddy, wheat, barley, oat, corn, millet, Chinese sorghum etc.), tuber crops (comprise sweet potato, potato, cassava etc.), beans (comprises soybean, broad bean, pea, mung bean, red bean etc.) and fiber (cotton, crudefiber crop, silkworm and mulberry etc.), oil plant (peanut, rape, sesame, soybean, Sunflower Receptacle etc.), sugar material (beet, sugarcane etc.), beverage (tealeaves, coffee, cocoa etc.), hobby (tobacco leaf etc.), medicinal (ginseng, the bulb of fritillary etc.), the torrid zone (rubber, coconut, oil palm, sisal hemp etc.) food crop and the fruit such as, flowers, oil plant, sugar material and cotton, fiber crops, tea, tobacco, the cash crop such as Chinese medicinal materials and plantation melon, really, tea, silkworm and mulberry, vegetables (containing various wild vegetable etc.), bamboo shoots, flowers and ornamental plant, hops, medicinal material, pepper, the garden crops such as seedling and other garden crops are as tobacco (flue-cured tobacco, air-curing of tobacco leaves, suncured tabacco), vegetables, (tomato, capsicum, radish, cucumber, Chinese cabbage, celery, hot pickled mustard tube, beet, rape, green onion, garlic etc.), melon (watermelon, muskmelon, hami melon, pawpaw etc.), beans (soybean, broad bean, pea-pods etc.), potato, wheat, corn, paddy rice, peanut, fruit tree, (apple, banana, citrus, peach, papaya), flowers (as orchid), potted landscape etc.Composition has improved the defence capability of plant in sterilization, makes plant produce the defence capability to pathogenic fungi, bacterium and virus infection.

Embodiment 7

5-methyl isophthalic acid of the present invention, 2,3-thiadiazoles connection-1,3-4-thiadiazoles derivative IV and intermediate III thereof and antiviral agent are combined in the application in control agricultural and forestry and gardening plant virus disease

5-methyl isophthalic acid, 2, 3-thiadiazoles connection-1, 3-4-thiadiazoles derivative IV and intermediate III thereof and existing Antiphytoviral medicament diazosulfide, tiadinil (TDL), isotianil (isotianil), 4-methyl isophthalic acid, 2, 3-thiadiazoles-5-formic acid, 4-methyl isophthalic acid, 2, 3-thiadiazoles-5-sodium formiate, 4-methyl isophthalic acid, 2, 3-thiadiazoles-5-ethyl formate, DL-beta-aminobutyric acid, virazole, antofine, Ningnanmycin, tisocromide, first thiophene lures amine or Whitfield's ointment, cytosintetidemycin, dichloro-isonicotinic acid, allyl isothiazole, well ridge azanol, any 1 or 2 compound combinations in jingganmycin, be used for preventing and treating agricultural plants virus disease, these virus diseases are selected from tobacco mosaic virus disease, various melon virus diseases, various solanaceous vegetables virus diseases, beans virus disease, Cruciferae virus disease, grain and oil crop virus disease, any in cotton virus disease and various fruit tree virus disease, wherein endanger serious being selected from: tobacco virus, peppery pimento virus disease, tomato virus disease, Chinese cabbage virus disease, Virus Diseases of Rice comprises rice dwarf virus disease, yellow dwart, stripe virus disease, fern leaf of tomato viral disease, pepper mosaic virus disease viral disease and tobacco veinal necrosis virus are sick, maize dwarf mosaic, cauliflower mosaic virus, oranges and tangerines virus disease, cymbidium mosaic virus, any in cybidium ring spot virus.The applicable crop of these compositions is selected from paddy, wheat, barley, oat, corn, Chinese sorghum, sweet potato, potato, cassava, soybean, pea-pods, broad bean, pea, mung bean, red bean, cotton, silkworm and mulberry, peanut, rape, sesame, Sunflower Receptacle, beet, sugarcane, coffee, cocoa, ginseng, the bulb of fritillary, rubber, coconut, oil palm, sisal hemp, tobacco, tomato, capsicum, radish, cucumber, Chinese cabbage, celery, hot pickled mustard tube, beet, rape, green onion, garlic, watermelon, muskmelon, hami melon, pawpaw, really, tea, wild vegetable, bamboo shoots, hops, potato, paddy rice, pepper, apple, banana, citrus, peach, papaya, orchid, the agriculturals such as potted landscape, gardening, economical, the plants such as forestry, the use of these compositions is improved the immunizing power of crop self, when producing the control of insect especially infection insect, has induced plant to produce the control to viral diseases of plants, also can produce the direct prevention effect of virus disease, therefore, these compositions can be for preparation and the purposes of Antiphytoviral medicament and inducing plant Antiphytoviral medicament.5-methyl isophthalic acid of the present invention, 2,3-thiadiazoles connection-1,3-4-thiadiazoles derivative IV and intermediate III thereof the total quality percentage composition in composition is 1%-90%, 5-methyl isophthalic acid of the present invention, the ratio of 2,3-thiadiazoles connection-1,3-4-thiadiazoles derivative IV and intermediate III and commercially available agricultural chemical is mass percent 1%: 99% to 99%: 1%, the formulation of composition processing is selected from wettable powder, sustained release dosage, pulvis, micro-capsule suspension, dispersible body preparation, dispersible solid preparation, seed treatment emulsion, aqueous emulsion, large granula, granule, microemulsion, oil-suspending agent, finish, seed with coated pesticidal, suspended emulsion agent, water-soluble granule, soluble thick agent, water-dispersible granules, poison grain, aerosol, block poison bait, sustained-release block, dense poison bait, CG/Encapsulated granule, capsule suspension, dispersible dense dose, pulvis, Waterless Seed Dressing pulvis, missible oil, electrostatic spray agent, water-in-oil emulsion, seed treatment agent, oil-in-water emulsion, smoke candle, granula subtilis, smoke candle, smoke cartridge, smog rod, seed treatment suspension agent, smog sheet, smoke substance, smog ball, granular poison bait, foaming agent, large granula, drift pulvis, granula, ointment, thermal fog, solid-liquid mixes dress agent, liquid/liquid mixes dress agent, cold mist agent, Gu Gu/mix filling agent, medicine paint, seed treatment liquor, microgranules, oil suspending agent, finish, oil-dispersing property pulvis, paste, sheet poison bait, dense jelly, sprinkle and water agent, stylus, seed coat agent, poison bait, basting agent, fritter poison bait, suspension agent, suspension emulsion, water-soluble granule, soluble thick agent, film forming finish, soluble powder, seed treatment water solube powder, ultra-low volume suspension agent, tablet, follow the trail of pulvis, ultra low volume liquids, steam releasing agent, water-dispersible granules, wettable powder, any one in wet-mixing kind water-dispersible powder, between these compositions, all show and be added or synergism, when keeping insecticidal activity, its antiviral activity is all greater than the effect that any one compound is used separately, find no the composition of antagonistic action, the drug effect lasting period of composition is long.

From the basic principles of chemistry, 5-methyl isophthalic acid, 2, 3-thiadiazoles connection-1, thereby 3-4-thiadiazoles derivative IV and intermediate III thereof can produce 5-methyl isophthalic acid from carbonyl fracture in plant with after water molecules effect, 2, 3-thiadiazoles-4-formic acid, by relevant software prediction and test, also confirm that compound of the present invention can produce 5-methyl isophthalic acid in the degraded of plant materials intracellular metabolite, 2, 3-thiadiazoles-4-formic acid, 5-methyl isophthalic acid, 2, 3-thiadiazoles-4-formic acid has inducing plant and produces the resistance to the phytopathy original, can be used in the control of Plant diseases and viral diseases of plants.Therefore, these compositions can be used in and prepare Antiphytoviral medicament and inducing plant Antiphytoviral medicament.Composition has improved the defence capability of plant in Antiphytoviral, makes plant produce the defence capability to pathogenic fungi, bacterium and virus infection.

Embodiment 8

5-methyl isophthalic acid of the present invention, complete processing and the stability of 2,3-thiadiazoles connection-1,3-4-thiadiazoles derivative IV and intermediate III and commercially available agricultural chemical compound preparation

5-methyl isophthalic acid of the present invention, 2, 3-thiadiazoles connection-1, the mixture complete processing of 3-4-thiadiazoles derivative IV and intermediate III thereof and commercially available agricultural chemical is in Table 4, from table 4, most medicament all can be processed according to the method for statement, the main component of liquid preparation is effective constituent and solubility promoter and tensio-active agent, synergistic agent, antifreezing agent, stablizer, other the component etc. such as thickening material or permeate agent, the composition of solid preparation mainly includes effect composition, the upper acceptable adjuvant component of other agriculturals such as tensio-active agent and filler, the cold storage test of process preparation, liquid preparation is placed 1 week without Precipitation at 0 ± 2 degree Celsius, solid preparation is placed 2 weeks at 54 ± 2 degrees Celsius, there is not caking phenomenon in medicament, all preparations store the medicament drug effect of placement front and back without significant difference, the rate of decomposition of composition effective constituent is in 5%, composite preparation qualified stability.

Table 15-methyl isophthalic acid, chemical structure and the physical and chemical parameter of 2,3-thiadiazoles connection-1,3-4-thiadiazoles derivative IV and intermediate III thereof

Table 1 5-methyl isophthalic acid of the present invention, chemical structure and the physical and chemical parameter (Continued) of 2,3-thiadiazoles connection-1,3-4-thiadiazoles derivative IV and intermediate III thereof

Table 25-methyl isophthalic acid, the biological activity (/ %) of 2,3-thiadiazoles connection-1,3-4-thiadiazoles derivative IV and intermediate III thereof

Compound number	AS	CA	GZ	PP	BC	SS	RC	PS	PI
										TN-TDZi1	17.86	40.00	9.76	40.54	45.16	15.15	64.81	28.75	29.63
TN-TDZ1	14.29	35.00	12.20	67.57	12.90	18.18	44.44	15.00	33.33
										TN-TDZi2	7.14	30.00	14.63	64.86	25.81	3.03	50.00	11.25	3.70
TN-TDZ2	14.29	30.00	17.07	59.46	25.81	15.15	44.44	15.00	11.11
										TN-TDZi3	16.13	25.00	40.00	30.00	67.86	34.15	52.38	54.79	36.67
TN-TDZ3	16.13	31.25	15.00	66.67	67.86	31.71	52.38	63.01	36.67
										TN-TDZi4	-	-	-	-	-	-	-	-	-
TN-TDZ4	25.81	12.50	17.50	60.00	46.43	43.90	57.14	75.34	43.33
										TN-TDZi5	27.59	17.65	75.44	43.33	21.74	9.30	62.22	58.21	30.00
TN-TDZ5	19.35	18.75	25.00	40.00	67.86	34.15	64.29	69.86	66.67
										TN-TDZi6	31.03	29.41	31.58	50.00	39.13	51.16	80.00	59.70	30.00
TN-TDZ6	37.93	23.53	50.88	30.00	26.09	53.49	57.78	49.25	40.00
										TN-TDZi7	34.48	47.06	33.33	73.33	69.57	74.42	80.00	56.72	6.67
TN-TDZ7	16.13	12.50	22.50	43.33	42.86	58.54	50.00	54.79	33.33
										TN-TDZi8	25.00	35.00	14.63	40.54	35.48	9.09	44.44	6.25	18.52
TN-TDZ8	17.86	15.00	19.51	27.03	12.90	24.24	31.48	12.50	3.70
										TN-TDZi9	7.14	45.00	43.90	72.97	77.42	48.48	94.44	57.50	37.04
TN-TDZ9	41.38	41.18	40.35	50.00	13.04	60.47	51.11	55.22	23.33
										TN-TDZi10	20.69	29.41	22.81	43.33	17.39	48.84	60.00	47.76	33.33
TN-TDZ10	48.28	11.76	28.07	33.33	21.74	41.86	62.22	53.73	40.00

Data are the measurement result of 50 mcg/ml; AS: tomato early blight bacterium (Alternaria solani); BC: botrytis cinerea pers (Botrytis cinerea); CA: peanut Cercospora bacteria (Cercospora arachidicola); GZ: fusarium graminearum (Gibberella zeae); PI: phytophthora infestans (Phytophthora infestans (Mont.) de Bary); PP: Botryosphaeria berengeriana f. sp (Physalospora piricola); PS: Rhizoctonia solani Kuhn (Pellicularia sasakii); RC: Rhizoctonia cerealis (Rhizoctonia cerealis); SS: Sclerotinia sclerotiorum (Sclerotinia sclerotiorum); ND: undetermined.

Table 35-methyl isophthalic acid, the activity of 2,3-thiadiazoles connection-1,3-4-thiadiazoles derivative IV and the anti-TMV of intermediate III thereof

Compound	Concentration/mg/L	Therapeutic activity	SD	Inactivate activity	SD	Prolection	SD	Induced activity	SD
										TN-TDZi1	100	50.85	4.49	44.44	5.09	22.89	4.34	16.02	4.84
TN-TDZ1	100	52.54	4.49	50.56	4.19	46.59	3.04	53.21	2.94
										TN-TDZi2	100	59.32	5.09	17.78	5.09	51.41	2.51	22.43	4.00
TN-TDZ2	100	29.38	5.95	32.22	5.09	26.91	2.51	37.82	4.84
										TN-TDZi3	100	14.94	3.04	42.46	2.48	29.78	1.68	26.67	4.41
TN-TDZ3	100	11.11	1.75	33.33	3.57	14.67	4.16	39.44	3.47
										TN-TDZi4	100	-	-	-	-	-	-	-	-
TN-TDZ4	100	15.71	2.89	21.83	2.99	50.89	3.01	46.67	5.00
										TN-TDZi5	100	19.21	5.18	42.22	5.09	40.56	4.87	10.90	4.00
TN-TDZ5	100	37.55	2.89	21.83	4.18	28.44	2.14	12.22	4.20
										TN-TDZi6	100	29.38	5.95	36.11	5.85	15.26	3.03	1538	1.93
TN-TDZ6	100	50.57	3.45	34.52	2.38	7.33	2.31	25.56	3.47
										TN-TDZi7	100	52.54	6.11	22.22	8.39	44.98	4.23	32.05	2.94
TN-TDZ7	100	39.08	3.45	8.33	2.38	14.44	2.14	25.00	4.41
										TN-TDZi8	100	28.81	4.48	18.89	5.09	33.33	2.5	28.85	3.85
TN-TDZ8	100	41.24	4.26	41.11	8.39	26.11	3.04	51.28	2.94
										TN-TDZi9	100	16.95	5.09	7.78	5.09	15.26	3.03	14.74	4.84
TN-TDZ9	100	59.32	4.49	33.33	6.67	27.31	3.03	22.44	2.94
										TN-TDZi10	100	59.89	5.95	39.44	8.22	14.46	3.19	10.90	4.00
TN-TDZ10	100	5.75	2.30	13.49	3.64	9.33	4.16	31.67	3.34
										TDL	100	19.44	1.39	31.86	1.70	22.92	2.95	49.15	1.96
Ningnanmycin	100	45.83	2.78	48.04	0.85	32.29	5.31	30.34	2.66
										Virazole	100	37.96	2.12	40.69	0.85	42.71	8.96	26.50	1.96

-: undetermined

Table 45-methyl isophthalic acid, 2,3-thiadiazoles connection-1,3-4-thiadiazoles derivative IV and the intermediate III working method mixed with commercially available agricultural chemical thereof

Claims (5)

1. a class 5-methyl isophthalic acid, 2,3-thiadiazoles connection, 1,3-4-thiadiazoles derivative, is characterized in that itself and its intermediate has suc as formula the chemical structure of general formula shown in IV and III:

Wherein, Ar is the group that is selected from phenyl, 4-fluorophenyl, 3-fluorophenyl, 2-nitrophenyl, 4-nitrophenyl, 3-chloro-phenyl-, 4-chloro-phenyl-, 4-aminomethyl phenyl, 3-aminomethyl phenyl, 3-p-methoxy-phenyl.

2. 5-methyl isophthalic acid claimed in claim 1, the synthetic method of 2,3-thiadiazoles connection 1,3-4-thiadiazoles derivative IV and intermediate III thereof, concrete synthetic route is as follows:

Wherein, Ar is the group that is selected from phenyl, 4-fluorophenyl, 3-fluorophenyl, 2-nitrophenyl, 4-nitrophenyl, 3-chloro-phenyl-, 4-chloro-phenyl-, 4-aminomethyl phenyl, 3-aminomethyl phenyl, 3-p-methoxy-phenyl;

Specifically be divided into following steps:

A. the preparation of intermediate N (2-(5-methyl isophthalic acid, 2,3-thiadiazoles-4-formohydrazide group) sulfo-acyl group) substituted benzamide III:

By the 5-methyl isophthalic acid of 3.33 mmoles, the replacement isothiocyanic acid ester II of 2,3-thiadiazoles-4-formyl hydrazine I, 3.33 mmoles and 20 milliliters of DMF join in 50 milliliters of three mouthfuls of round-bottomed flasks, room temperature; Stir 6 hours; There is white solid, filter gained solid alcohol recrystallization, yield 60%-90%, measure fusing point and ¹hNMR, the amount of synthetic compound III expands or dwindles by corresponding proportion, and the volume of reaction vessel expands or dwindles by corresponding proportion;

B.5-methyl isophthalic acid, the preparation of 2,3-thiadiazoles connection, 1,3-4-thiadiazoles derivative IV:

N-(2-(5-methyl isophthalic acid, 2,3-thiadiazoles-4-formohydrazide group) sulfo-acyl group) the substituted benzamide III, 20 methyl alcohol, the 0.1 milliliter of vitriol oil that in 50 milliliters of round-bottomed flasks, add 3.0 mmoles, stirring and refluxing 6 hours; There is white solid, filter gained solid alcohol recrystallization, yield 60%-90%, measure fusing point and ¹hNMR, the amount of synthetic compound IV expands or dwindles by corresponding proportion, and the volume of reaction vessel expands or dwindles by corresponding proportion.

3. 5-methyl isophthalic acid claimed in claim 1, the purposes of 2,3-thiadiazoles connection, 1,3-4-thiadiazoles derivative IV in preparing sterilant.

4. 5-methyl isophthalic acid claimed in claim 1, the purposes of 2,3-thiadiazoles connection, 1,3-4-thiadiazoles derivative IV in preparing anti-plant virus agent.

5. 5-methyl isophthalic acid claimed in claim 1, the purposes of 2,3-thiadiazoles connection, 1,3-4-thiadiazoles derivative IV in preparing activating plants agent.