CN101875644A - Thiadiazoles heterocyclic compounds and synthesis methods and applications thereof - Google Patents

Abstract

The invention provides derivatives containing 4-methyl-1,2,3-thiadiazole and synthesis methods and applications thereof. The invention relates to heterocyclic compounds containing 1,2-diazole, in particular to 4-methyl-1,2,3-thiadiazole. The chemical general formula of the heterocyclic compounds is shown in the specification, wherein R1 is C1-C6 linear alkyl, C3-C6 naphthenic base, phenyl or substituted phenyl; R2 is phenyl or substituted phenyl; and R3 is cyclohexyl or isopropyl. The invention discloses the chemical structures and the synthesis methods of the compounds and applications of the compounds in protecting the plants in the fields of agriculture and horticulture and controlling plant virus diseases, fungal diseases, bacterioses and pests, and simultaneously discloses the applications of the compounds in inducing the agricultural and horticultural plants to generate disease-resistant effects and protecting the plants in the fields of agriculture and horticulture and the application of the compounds in controlling the viruses, pathogenic bacteria and agricultural insects in the agricultural and horticultural plants by being combined with the commercial anti-virus drugs, bactericides and insecticides.

Description

Thiadiazoles heterocyclic compounds and preparation method and use thereof

Technical field

Technical scheme of the present invention relates to the heterogeneous ring compound that contains 1,2-diazole, is specifically related to contain 1,2, the 3-thiadiazoles derivative.

Background technology

Heterogeneous ring compound is the important source with lead compound of physiologically active; at present in the patent of application; the half new compound is heterogeneous ring compound not all; 1; 2; the 3-thiadiazoles has wide biological activity; tiadinil (TDL) and diazosulfide (BTH) all are commercial plant activator; the plant activator is one of important research direction of plant protection from now on; this compounds is " environment friendly agricultural " truly; the contriver is in state natural sciences fund (20672062 and 20872071); under the subsidy of " 973 " plans (2003CB114402) and Tianjin natural science fund (07JCYBJC01200) and Tianjin science and technology support plan International Technology collaborative project (07ZCGHHZ01400) and state natural sciences fund international cooperative research project (20911120069); BTH and TDL series derivates have been synthesized in design, find that N-(5-methyl-1,3-thiazole-2-yl)-4-methyl-1,2,3-thiadiazole has good induced activity (ZL 2,006 1 0013185.5).

Polycomponent Ugi reaction is a kind of by the four component condensation reactions of the orientation between aldehyde, amine, acid and the isonitrile, in combinatorial chemistry, be widely used, good stereoselectivity is arranged, based on the appropriate design of reactive component functional group, solid state reaction and complete synthesis in be widely used, this reaction has good Atom economy, belong to the Green Chemistry reaction, its reaction mechanism is as follows:

Our early-stage Study is utilized Ugi reaction having carried out exploratory study, synthesized the part new compound, part of compounds has certain induced activity, part of compounds has certain fungicidal activity (CN101250167A), the present invention carries out deep structure to this compounds and derives, from the principle of active substructure splicing, with the R in the patent in early stage (CN101250167A) ₁Group is changed over by alkyl that the direct antiviral activity of synthetic part of compounds has obtained beyond thought raising behind the phenyl that contains phenyl or replacement, and R of the present invention ₁For its direct antiviral activity of part derivative of alkyl and protection activity and therapeutic activity are greatly improved.

Summary of the invention

Technical problem to be solved by this invention is: new various N-replacement-4-methyl isophthalic acids are provided; 2; the synthetic method of 3-thiadiazoles derivative; provide the activity of activity that this compounds suppresses pathogenic fungi and inducing anti-disease and direct anti-phytoviral activity as activity and the protection activity and the therapeutic activity of the withered spot method of half leaf, provide these compounds simultaneously as agrochemicals application in plant protection at agriculture field and gardening field.

The present invention solves this technical problem the technical scheme that is adopted: have the N-replacement-4-methyl isophthalic acid of fungicidal activity and induced activity and direct antiviral activity, and 2, the chemical structure of general formula of 3-thiadiazoles derivative is as figure I, and the chemical structure of particular compound sees Table 1:

Wherein: R ₁Be n-propyl, R ₃During for cyclohexyl, R ₂The phenyl that replaces for Chloro-O-Phenyl, a chloro-phenyl-, rubigan, adjacent fluorophenyl, a fluorophenyl, to fluorophenyl, o-trifluoromethyl phenyl, m-trifluoromethylphenyl, p-trifluoromethyl phenyl, ortho-nitrophenyl base, m-nitro base, p-nitrophenyl, o-methyl-phenyl-, an aminomethyl phenyl, p-methylphenyl, p-hydroxybenzene etc.;

R ₁For to methyl Chloro-O-Phenyl, R ₃During for cyclohexyl, R ₂The phenyl that replaces for phenyl, Chloro-O-Phenyl, a chloro-phenyl-, rubigan, adjacent fluorophenyl, a fluorophenyl, to fluorophenyl, o-trifluoromethyl phenyl, m-trifluoromethylphenyl, p-trifluoromethyl phenyl, ortho-nitrophenyl base, m-nitro base, p-nitrophenyl, o-methyl-phenyl-, an aminomethyl phenyl, p-methylphenyl, a hydroxy phenyl, p-hydroxybenzene etc.;

R ₁For to the adjacent fluorophenyl of methyl, R ₃During for cyclohexyl, R ₂The phenyl that replaces for Chloro-O-Phenyl, a chloro-phenyl-, rubigan, adjacent fluorophenyl, a fluorophenyl, to fluorophenyl, o-trifluoromethyl phenyl, m-trifluoromethylphenyl, p-trifluoromethyl phenyl, ortho-nitrophenyl base, m-nitro base, p-nitrophenyl, o-methyl-phenyl-, an aminomethyl phenyl, p-methylphenyl, p-hydroxybenzene etc.;

R ₁For to the adjacent fluorophenyl of methyl, R ₃During for sec.-propyl, R ₂The phenyl that replaces for phenyl, Chloro-O-Phenyl, a chloro-phenyl-, rubigan, adjacent fluorophenyl, a fluorophenyl, to fluorophenyl, o-trifluoromethyl phenyl, m-trifluoromethylphenyl, p-trifluoromethyl phenyl, ortho-nitrophenyl base, m-nitro base, p-nitrophenyl, o-methyl-phenyl-, an aminomethyl phenyl, p-methylphenyl, a hydroxy phenyl, p-hydroxybenzene etc.

The 4-methyl isophthalic acid that contains of the present invention, 2, the synthetic method of 3-thiadiazoles Hete rocyclic derivatives is as follows:

Wherein: R ₁For cycloalkyl, the phenyl of the straight chained alkyl of C1-C6, C3-C6 or be substituted that base is single to be replaced or disubstituted phenyl, described substituting group for be selected from methyl and (or) group of halogen; R ₂For be selected from phenyl, Chloro-O-Phenyl, a chloro-phenyl-, rubigan, adjacent fluorophenyl, a fluorophenyl, to the group of fluorophenyl, o-trifluoromethyl phenyl, m-trifluoromethylphenyl, p-trifluoromethyl phenyl, ortho-nitrophenyl base, m-nitro base, p-nitrophenyl, o-methyl-phenyl-, an aminomethyl phenyl, p-methylphenyl, p-hydroxybenzene; R ₃For being selected from the group of cyclohexyl or sec.-propyl.

Specifically be divided into following steps:

A. contain the 4-methyl isophthalic acid, 2, the preparation of 3-thiadiazoles Hete rocyclic derivatives (ZX-U series):

In 50 milliliters of round-bottomed flasks, add 10mL methyl alcohol, add the 4-methyl isophthalic acid of own synthetic or purchase again, 2,3-thiadiazoles-5-formic acid, aminated compounds R ₁NH ₂With aldehyde compound R ₂CHO and isonitrile compounds R ₃Each 3 mmole of NC, with reaction system at room temperature stirring reaction refluxed again after 2 hours 3 hours, after reaction finished, decompression desolventizing, solid washed with saturated sodium carbonate after washing with dilute hydrochloric acid again, use 200～300 order silica gel column chromatographies at last, eluent is the sherwood oil of 60～90 degree: ethyl acetate, and according to the difference of product, volume ratio is between 8: 1～1: 5, with the pure product calculated yield of gained, measure fusing point, carry out MS and ¹The mensuration of HNMR, the consumption of synthetic compound enlarges by corresponding proportion or dwindles;

B. contain the 4-methyl isophthalic acid, 2, the mensuration that 3-thiadiazoles heterocyclic derivative influences the pathogenic fungi growth activity:

4-methyl isophthalic acid of the present invention, 2, the measuring method of 3-thiadiazoles derivative fungicidal activity or bacteriostatic activity is as follows:

Adopt thalli growth rate assay method, detailed process is, get 5 milligrams of sample dissolution in an amount of 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 9 milliliters of substratum more respectively, make 50 mcg/ml pastille flat boards after shaking up, do blank with the flat board that adds 1 milliliter of aqua sterilisa, punch tool with 4 millimeters of diameters cuts the bacterium dish along the mycelia outer rim, move on the pastille flat board, being equilateral triangle puts, every processing repeats 3 times, culture dish is placed in 24 ± 1 degree constant incubators cultivates, and colony diameter to be contrasted expands to 2～3 centimetres of " Invest, Then Investigate "s and respectively handles bacterium dish expansion diameter, average, relatively calculate relative bacteriostasis rate with blank, comprise frequently seen plants pathogenic bacteria on the various agricultural for the examination bacterial classification, as: CB: sugar beet leaf spot bacteria (Cercospora beticola); FO: cucumber fusarium axysporum (Fusarium oxysporum); CA: peanut Cercospora bacteria (Cercospora arachidicola); AS: tomato early blight bacterium (Alternaria solani); GZ: fusarium graminearum (Gibberella zeae); PP: ring rot of apple bacterium (Physalospora piricola); BC: botrytis cinerea pers (Botrytis cinerea); PO: rice blast fungus (Phyricularia oryzae); PS: Rhizoctonia solani Kuhn (Pellicularia sasakii); CL watermelon anthrax bacteria: (Colletotrichum lagenarium); RS: dry thread Pyrenomycetes (Rhizoctonia solani); PI: phytophthora infestans (Phytophthora infestans (Mont.) de Bary) etc.;

C. the 4-methyl isophthalic acid that contains of the present invention, 2, the active mensuration of 3-thiadiazoles heterocyclic derivative living body biological:

4-methyl isophthalic acid of the present invention, 2, the active mensuration of the anti-TMV of the Hete rocyclic derivatives of 3-thiadiazoles adopts the withered spot method of half leaf to carry out; The direct antiviral activity of live body is measured and is comprised that protection mensuration active and therapeutic activity adopts frictional inoculation method to carry out; The activity of evoking tobacco resisting tobacco mosaic virus adopts live body to induce the method for frictional inoculation to carry out.

The invention has the beneficial effects as follows: the present invention is to plant activator N-(5-methyl-1,3-thiazole-2-yl)-4-methyl-1,2,3-thiadiazole-with independent intellectual property right 1; 2; the derivative of 3-thiadiazoles-the carried out optimization of the first guide structure of system; utilize the principle design of active substructure splicing to synthesize serial new compound and the synthetic new compound has been carried out wide biological activity mensuration; the activity of measuring comprises that fungicidal activity and direct anti-phytoviral activity and inducing plant produce the activity of disease resistance, and this compounds can be used for the plant protection in agriculture field and gardening field.

The present invention will more specifically describe by specific preparation and biological activity determination embodiment and contain the 4-methyl isophthalic acid, 2, synthetic and the biological activity and the purposes of the Hete rocyclic derivatives of 3-thiadiazoles or N-(5-methyl-1,3-thiazole-2-yl)-4-methyl-1,2,3-thiadiazole derivative, but described embodiment only is used for specific description the present invention and unrestricted the present invention, especially its bioactive research only illustrates, rather than the restriction this patent, concrete embodiment is as follows:

Embodiment 1: the synthetic and structure of compound ZX-2-2 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2, each 3 mmole of 3-thiadiazoles-5-formic acid, Tri N-Propyl Amine and o-chlorobenzaldehyde and cyclohexyl isonitrile, with reaction system at room temperature stirring reaction separate out solid rapidly, get product with methanol wash, yield: 56%, fusing point: 159-162 degree, HRMS (m/z): 457.1443 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.62-7.23 (m, 4H), 6.21 (m, 1H), 5.63 (m, 1H), 3.87-3.83 (m, 1H), 3.16-2.94 (m, 2H), 2.78 (s, 3H), 1.93-0.40 (m, 15H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 2: the synthetic and structure of compound ZX-2-3 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2, each 3 mmole of 3-thiadiazoles-5-formic acid, Tri N-Propyl Amine and m chlorobenzaldehyde and cyclohexyl isonitrile are with reaction system stirring reaction after 5 hours at room temperature, desolventizing, (eluent is the sherwood oil of 60～90 degree: ethyl acetate) (volume ratio is 3: 1) gets pure product to use 200～300 order silica gel column chromatographies at last, yield: 58%, fusing point: 89-92 degree, HRMS (m/z): 457.1443 (M+23); ¹HNMR (solvent: CDCl ₃, chemical shift): δ 7.38-7.36 (m, 4H), 5.78-5.70 (m, 2H), 3.87-3.78 (m, 1H), 3.19 (m, 2H), 2.77 (s, 3H), 1.93-0.52 (m, 15H).Its ¹HNMR and MS data presentation are consistent with its chemical structure.

Embodiment 3: the synthetic and structure of compound ZX-2-4 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2, each 3 mmole of 3-thiadiazoles-5-formic acid, Tri N-Propyl Amine and 4-chloro-benzaldehyde and cyclohexyl isonitrile are with reaction system stirring reaction at room temperature, spend the night and separate out solid, get product with methanol wash, yield: 30%, fusing point: 127-131 degree, HR MS (m/z): 457.1428 (M+23), 457.00 (M+1); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.41 (m, 4H), 5.78-5.59 (m, 2H), 3.87-3.78 (m, 1H), 3.19 (m, 2H), 2.78 (s, 3H), 1.93-0.52 (m, 15H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 4: the synthetic and structure of compound ZX-2-5 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2, each 3 mmole of 3-thiadiazoles-5-formic acid, Tri N-Propyl Amine and adjacent fluorobenzaldehyde and cyclohexyl isonitrile are with reaction system stirring reaction after 5 hours at room temperature, desolventizing, (eluent is the sherwood oil of 60～90 degree: ethyl acetate) (volume ratio is 3: 1) gets pure product to use 200～300 order silica gel column chromatographies at last, yield: 52%, fusing point: 98-101 degree, HR MS (m/z): 441.1729 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.60-7.10 (m, 4H), 6.11-5.79 (m, 2H), 3.89-3.79 (m, 1H), 3.22-3.12 (m, 2H), 2.75 (s, 3H), 1.94-0.49 (m, 15H).Its ¹HNMR and MS data presentation are consistent with its chemical structure.

Embodiment 5: the synthetic and structure of compound ZX-2-6 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2, each 3 mmole of 3-thiadiazoles-5-formic acid, Tri N-Propyl Amine and a fluorobenzaldehyde and cyclohexyl isonitrile, with reaction system stirring reaction after 5 hours at room temperature, desolventizing, use at last 200～300 order silica gel column chromatographies (eluent is the sherwood oils of 60～90 degree: ethyl acetate) (volume ratio is 3: 1) pure product, yield: 57%, fusing point: 94-96 degree HR MS (m/z): 441.1727 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.44-7.09 (m, 4H), 5.78-5.66 (m, 2H), 3.84-3.82 (m, 1H), 3.21-3.18 (m, 2H), 2.78 (s, 3H), 1.94-0.52 (m, 15H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 6: the synthetic and structure of compound ZX-2-7 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2, each 3 mmole of 3-thiadiazoles-5-formic acid, Tri N-Propyl Amine and p-Fluorobenzenecarboxaldehyde and cyclohexyl isonitrile, with reaction system at room temperature stirring reaction slowly separate out crystal, get product with methanol wash, yield: 15%, fusing point: 115-120 degree, HRMS (m/z): 441.1729 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.46-7.09 (m, 4H), 5.82-5.58 (m, 2H), 3.89-3.77 (m, 1H), 3.18-3.13 (m, 2H), 2.77 (s, 3H), 1.93-0.49 (m, 15H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 7: the synthetic and structure of compound ZX-2-8 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2, each 3 mmole of 3-thiadiazoles-5-formic acid, Tri N-Propyl Amine and 2-(Trifluoromethyl) benzaldehyde and cyclohexyl isonitrile, with reaction system at room temperature stirring reaction slowly separate out crystal, get product with methanol wash, yield: 89%, fusing point: 75-80 degree, HR MS (m/z): 491.1697 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.81-7.55 (m, 4H), 6.16 (m, 1H), 5.33 (m, 1H), 3.85-3.79 (m, 1H), 3.16-2.93 (m, 2H), 2.77 (s, 3H), 1.95-0.41 (m, 15H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 8: the synthetic and structure of compound ZX-2-9 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2, each 3 mmole of 3-thiadiazoles-5-formic acid, Tri N-Propyl Amine and m-trifluoromethyl phenyl aldehyde and cyclohexyl isonitrile, dry solvent and separate out crystal, get product, yield: 26% with methanol wash, fusing point: 124-126 degree, HR MS (m/z): 491.1694 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.70-7.54 (m, 4H), 5.89-5.76 (m, 2H), 3.90-3.81 (m, 1H), 3.21-3.17 (m, 2H), 2.78 (s, 3H), 1.95-0.52 (m, 15H).Its ¹HNMR and MS data presentation are consistent with its chemical structure.

Embodiment 9: the synthetic and structure of compound ZX-2-10 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2,3-thiadiazoles-5-formic acid, Tri N-Propyl Amine and to trifluoromethylated benzaldehyde and each 3 mmole of cyclohexyl isonitrile, with reaction system stirring reaction after 5 hours at room temperature, desolventizing, (eluent is the sherwood oil of 60～90 degree: ethyl acetate) (volume ratio is 3: 1) gets pure product to use 200～300 order silica gel column chromatographies at last, yield: 58%, fusing point: 149-153 degree, HR MS (m/z): 491.1704 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.71-7.61 (m, 4H), 5.81-5.72 (m, 2H), 3.89-3.79 (m, 1H), 3.20 (m, 2H), 2.78 (s, 3H), 1.95-0.53 (m, 15H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 10: the synthetic and structure of compound ZX-2-11 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2, each 3 mmole of 3-thiadiazoles-5-formic acid, Tri N-Propyl Amine and m-nitrobenzaldehyde and cyclohexyl isonitrile, dry solvent and separate out crystal, get product, yield: 64% with methanol wash, fusing point: 86-88 degree, HR MS (m/z): 468.1669 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 8.03-7.58 (m, 4H), 6.29-6.28 (m, 1H), 5.87 (m, 1H), 3.85-3.79 (m, 1H), 3.21 (m, 2H), 2.79 (s, 3H), 1.94-0.55 (m, 15H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 11: the synthetic and structure of compound ZX-2-12 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2, each 3 mmole of 3-thiadiazoles-5-formic acid, Tri N-Propyl Amine and m-nitrobenzaldehyde and cyclohexyl isonitrile, with reaction system stirring reaction after 48 hours at room temperature, desolventizing, (eluent is the sherwood oil of 60～90 degree: ethyl acetate) (volume ratio is 3: 1) gets pure product to use 200～300 order silica gel column chromatographies at last, yield: 45%, fusing point: 204-207 degree, HR MS (m/z): 491.1704 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.54-6.89 (m, 4H), 5.89-5.75 (m, 2H), 3.80-3.78 (m, 1H), 3.20-2.73 (m, 2H), 2.73 (s, 3H), 1.87-0.46 (m, 15H).Its ¹H NMR shows consistent with its chemical structure.

Embodiment 12: the synthetic and structure of compound ZX-2-13 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2, each 3 mmole of 3-thiadiazoles-5-formic acid, Tri N-Propyl Amine and paranitrobenzaldehyde and cyclohexyl isonitrile with reaction system stirring reaction at room temperature, are separated out solid after the week, get product with methanol wash, yield: 33%, fusing point: 123-129 degree, HR MS (m/z): 468.1674 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 8.29-7.26 (m, 4H), 5.88-5.80 (m, 2H), 3.89-3.80 (m, 1H), 3.24 (m, 2H), 2.78 (s, 3H), 1.95-0.57 (m, 15H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 13: the synthetic and structure of compound ZX-2-14 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2, each 3 mmole of 3-thiadiazoles-5-formic acid, Tri N-Propyl Amine and o-methyl-benzene formaldehyde and cyclohexyl isonitrile with reaction system stirring reaction at room temperature, dry solvent and separate out solid, get product with methanol wash, yield: 48%, fusing point: 153-156 degree, HR MS (m/z): 437.1977 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.35-7.22 (m, 4H), 6.25 (m, 1H), 5.40 (m, 1H), 3.90-3.80 (m, 1H), 3.13 (m, 2H), 2.80 (s, 3H), 2.37 (s, 3H), 1.95-0.32 (m, 15H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 14: the synthetic and structure of compound ZX-2-15 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2, each 3 mmole of 3-thiadiazoles-5-formic acid, Tri N-Propyl Amine and a tolyl aldehyde and cyclohexyl isonitrile, at room temperature stirring reaction is after 5 hours with reaction system, and (eluent is the sherwood oil of 60～90 degree: ethyl acetate) (volume ratio is 3: 1) gets pure product, yield: 78% with 200～300 order silica gel column chromatographies behind the desolventizing, fusing point: 98-102 degree, HR MS (m/z): 437.1978 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.33-7.21 (m, 4H), 5.85-5.51 (m, 1H), 3.85-3.82 (m, 1H), 3.17 (m, 2H), 2.79 (s, 3H), 2.38 (s, 3H), 1.93-0.47 (m, 15H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 15: the synthetic and structure of compound ZX-2-16 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2, each 3 mmole of 3-thiadiazoles-5-formic acid, Tri N-Propyl Amine and p-tolyl aldehyde and cyclohexyl isonitrile, at room temperature stirring reaction is after 5 hours with reaction system, and (eluent is the sherwood oil of 60～90 degree: ethyl acetate) (volume ratio is 3: 1) gets pure product, yield: 29% with 200～300 order silica gel column chromatographies behind the desolventizing, fusing point: 149-153 degree, HR MS (m/z): 437.1980 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.34-7.21 (m, 4H), 5.83-5.50 (m, 2H), 3.87-3.79 (m, 1H), 3.15 (m, 2H), 2.79 (s, 3H), 2.39 (s, 3H), 1.91-0.45 (m, 15H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 16: the synthetic and structure of compound ZX-2-17 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2, each 3 mmole of 3-thiadiazoles-5-formic acid, Tri N-Propyl Amine and p-Hydroxybenzaldehyde and cyclohexyl isonitrile, after 5 hours, (eluent is the sherwood oil of 60～90 degree: ethyl acetate) (volume ratio is 3: 1) gets pure product, yield: 19% to reaction system with 200～300 order silica gel column chromatographies behind the desolventizing in the stirring at room reaction, fusing point: 178-183 degree, HR MS (m/z): 439.1771 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.35-6.87 (m, 4H), 5.81-5.22 (m, 3H), 3.83-3.81 (m, 1H), 3.15 (m, 2H), 2.79 (s, 3H), 2.39 (s, 3H), 1.91-0.46 (m, 15H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 17: the synthetic and structure of compound ZX-3-1 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2,3-thiadiazoles-5-formic acid, to methyl Ortho-Chloro aniline and phenyl aldehyde and each 3 mmole of cyclohexyl isonitrile, with reaction system at room temperature stirring reaction separated out white solid in 1 minute, methyl alcohol wash product, yield: 50%, fusing point: 175-180 degree, HR MS (m/z): 505.1433 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.29-6.94 ((m, 8H), 6.17 (s, 1H), 5.39-5.38 (d, J=8Hz, 1H), 3.90-3.82 (m, 1H), 2.87 (s, 3H), 2.25 (s, 3H), 1.99-1.00 (m, 10H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 18: the synthetic and structure of compound ZX-3-2 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid again, 2,3-thiadiazoles-5-formic acid, to methyl Ortho-Chloro aniline and o-chlorobenzaldehyde and each 3 mmole of cyclohexyl isonitrile, reaction system was separated out white solid in 2 days in stirring at room reaction, methyl alcohol wash product, yield: 52%, fusing point: 176-180 degree, HR MS (m/z): 529.1047 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.39-6.89 ((m, 7H), 6.57 (s, 1H), 5.51-5.49 (d, J=8Hz, 1H), 3.92-3.85 (m, 1H), 2.86 (s, 3H), 2.21 (s, 3H), 2.05-1.01 (m, 10H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 19: the synthetic and structure of compound ZX-3-3 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2,3-thiadiazoles-5-formic acid, to methyl Ortho-Chloro aniline and m chlorobenzaldehyde and each 3 mmole of cyclohexyl isonitrile, with reaction system at room temperature stirring reaction separated out white solid in 10 minutes, methyl alcohol wash product, yield: 76%, fusing point: 198-203 degree, HR MS (m/z): 539.1041 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.28-7.01 (m, 7H), 6.08 (s, 1H), 5.45-5.44 (d, J=8Hz, 1H), 3.89-3.81 (m, 1H), 2.87 (s, 3H), 2.28 (s, 3H), 2.00-1.03 (m, 10H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 20: the synthetic and structure of compound ZX-3-4 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid again, 2,3-thiadiazoles-5-formic acid, to methyl Ortho-Chloro aniline and 4-chloro-benzaldehyde and each 3 mmole of cyclohexyl isonitrile, with reaction system at room temperature stirring reaction separated out white solid in 1 minute, methyl alcohol wash product, yield: 78%, fusing point: 215-218 degree, HR MS (m/z): 539.1038 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.24-6.97 (m, 7H), 6.11 (s, 1H), 5.41-5.39 (d, J=8Hz, 1H), 3.88-3.81 (m, 1H), 2.87 (s, 3H), 2.28 (s, 3H), 2.00-1.02 (m, 10H.Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 21: the synthetic and structure of compound ZX-3-5 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2,3-thiadiazoles-5-formic acid, to methyl Ortho-Chloro aniline and adjacent fluorobenzaldehyde and each 3 mmole of cyclohexyl isonitrile, with reaction system at room temperature stirring reaction separated out white solid in 1 minute, methyl alcohol wash product, yield: 55%, fusing point: 132-135 degree, HR MS (m/z): 523.1341 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.29-6.93 ((m, 7H), 6.44 (s, 1H), 5.44-5.42 (d, J=8Hz, 1H), 3.93-3.84 (m, 1H), 2.86 (s, 3H), 2.23 (s, 3H), 2.03-1.01 (m, 10H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 22: the synthetic and structure of compound ZX-3-6 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid again, 2,3-thiadiazoles-5-formic acid, to methyl Ortho-Chloro aniline and a fluorobenzaldehyde and each 3 mmole of cyclohexyl isonitrile, reaction system was separated out white solid in 2 minutes in stirring at room reaction, methyl alcohol wash product, yield: 72%, fusing point: 206-208 degree, HR MS (m/z): 523.1348 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.25-6.91 (m, 7H), 6.10 (s, 1H), 5.45-5.43 (d, J=8Hz, 1H), 3.89-3.82 (m, 1H), 2.87 (s, 3H), 2.27 (s, 3H), 2.01-1.03 (m, 10H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 23: the synthetic and structure of compound ZX-3-7 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid again, 2,3-thiadiazoles-5-formic acid, to methyl Ortho-Chloro aniline and p-Fluorobenzenecarboxaldehyde and each 3 mmole of cyclohexyl isonitrile, reaction system was separated out white solid in 2 minutes in stirring at room reaction, methyl alcohol wash product, yield: 89%, fusing point: 213-217 degree, HR MS (m/z): 523.1348 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.16-6.92 (m, 7H), 6.14 (s, 1H), 5.41-5.39 (d, J=8Hz, 1H), 3.89-3.81 (m, 1H), 2.87 (s, 3H), 2.27 (s, 3H), 2.01-1.02 (m, 10H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 24: the synthetic and structure of compound ZX-3-8 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2,3-thiadiazoles-5-formic acid, to methyl Ortho-Chloro aniline and m-hydroxybenzaldehyde and each 3 mmole of cyclohexyl isonitrile, with reaction system stirring reaction at room temperature, desolventizing, (eluent is the sherwood oil of 60～90 degree: ethyl acetate) (volume ratio is 3: 1) gets pure product to use 200～300 order silica gel column chromatographies at last, yield: 8%, fusing point: 152-158 degree, HR MS (m/z): 573.1304 (M+23).The MS data presentation is consistent with its chemical structure.

Embodiment 25: the synthetic and structure of compound ZX-3-9 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid again, 2,3-thiadiazoles-5-formic acid, to methyl Ortho-Chloro aniline and m-trifluoromethyl phenyl aldehyde and each 3 mmole of cyclohexyl isonitrile, with reaction system at room temperature stirring reaction separated out white solid in 5 minutes, methyl alcohol wash product, yield: 48%, fusing point: 205-207 degree, HR MS (m/z): 573.1308 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.54-6.95 ((m, 7H), 6.20 (s, 1H), 5.50-5.48 (d, J=8Hz, 1H), 3.90-3.83 (m, 1H), 2.88 (s, 3H), 2.26 (s, 3H), 2.02-1.02 (m, 10H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 26: the synthetic and structure of compound ZX-3-10 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2,3-thiadiazoles-5-formic acid, to the methyl Ortho-Chloro aniline with to each 3 mmole of trifluoromethylated benzaldehyde and cyclohexyl isonitrile, with reaction system at room temperature stirring reaction separate out white solid, methyl alcohol wash product, yield: 81%, fusing point: 214-216 degree, HR MS (m/z): 573.1304 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.54-6.98 (m, 7H), 6.16 (s, 1H), 5.45-5.43 (d, J=8Hz, 1H), 3.88-3.84 (m, 1H), 2.88 (s, 3H), 2.28 (s, 3H), 1.98-1.02 (m, 10H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 27: the synthetic and structure of compound ZX-3-11 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid again, 2,3-thiadiazoles-5-formic acid, to methyl Ortho-Chloro aniline and Ortho Nitro Benzaldehyde and each 3 mmole of cyclohexyl isonitrile, reaction system was separated out white solid in 2 days in stirring at room reaction, methyl alcohol wash product, yield: 45%, fusing point: 171-173 degree, HR MS (m/z): 550.1288 (M+23); HR MS (m/z): δ 7.93-6.91 ((m, 7H), 6.63 (s, 1H), 5.67-5.65 (d, J=8Hz, 1H), 3.88-3.81 (m, 1H), 2.86 (s, 3H), 2.21 (s, 3H), 2.03-1.01 (m, 10H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 28: the synthetic and structure of compound ZX-3-12 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2,3-thiadiazoles-5-formic acid, to methyl Ortho-Chloro aniline and m-nitrobenzaldehyde and each 3 mmole of cyclohexyl isonitrile, with reaction system at room temperature stirring reaction separate out white solid, methyl alcohol wash product, yield: 71%, fusing point 204-208 degree, HR MS (m/z): 550.1285 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 8.16-7.00 ((m, 7H), 6.21 (s, 1H), 5.60-5.58 (d, J=8Hz, 1H), 3.90-3.84 (m, 1H), 2.89 (s, 3H), 2.27 (s, 3H), 2.03-1.05 (m, 10H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 29: the synthetic and structure of compound ZX-3-13 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2,3-thiadiazoles-5-formic acid, to methyl Ortho-Chloro aniline and paranitrobenzaldehyde and each 3 mmole of cyclohexyl isonitrile, with reaction system at room temperature stirring reaction separated out white solid in 25 minutes, methyl alcohol wash product, yield: 75%, fusing point: 113-115 degree, HRMS (m/z): 550.1287 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 8.12-7.00 ((m, 7H), 6.18 (s, 1H), 5.56-5.54 (d, J=8Hz, 1H), 3.90-3.83 (m, 1H), 2.88 (s, 3H), 2.28 (s, 3H), 2.02-1.04 (m, 10H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 30: the synthetic and structure of compound ZX-3-14 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid again, 2,3-thiadiazoles-5-formic acid, to methyl Ortho-Chloro aniline and a tolyl aldehyde and each 3 mmole of cyclohexyl isonitrile, reaction system is reacted desolventizing in stirring at room, and (eluent is the sherwood oil of 60～90 degree: ethyl acetate) (volume ratio is 3: 1) gets pure product, yield: 47% to use 200～300 order silica gel column chromatographies at last, fusing point: 131-134 degree, HR MS (m/z): 519.1591 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.20-6.81 ((m, 7H), 6.51 (s, 1H), 5.30-5.28 (d, J=8Hz, 1H), 3.92-3.84 (m, 1H), 2.88 (s, 3H), 2.43 (s, 3H), 2.22 (s, 3H), 1.98-1.00 (m, 10H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 31: the synthetic and structure of compound ZX-3-15 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2,3-thiadiazoles-5-formic acid, to methyl Ortho-Chloro aniline and a tolyl aldehyde and each 3 mmole of cyclohexyl isonitrile, with reaction system at room temperature stirring reaction separated out white solid in 7 minutes, methyl alcohol wash product, yield: 46%, fusing point: 172-173 degree, HR MS (m/z): 519.1598 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.14-6.89 ((m, 7H), 6.13 (s, 1H), 5.39-5.37 (d, J=8Hz, 1H), 3.89-3.82 (m, 1H), 2.87 (s, 3H), 2.26 (s, 6H), 1.99-1.01 (m, 10H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 32: the synthetic and structure of compound ZX-3-16 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2,3-thiadiazoles-5-formic acid, to methyl Ortho-Chloro aniline and p-tolyl aldehyde and each 3 mmole of cyclohexyl isonitrile, with reaction system at room temperature stirring reaction separated out white solid in 5 minutes, methyl alcohol wash product, yield: 60%, fusing point: 209-211 degree, HR MS (m/z): 519.1593 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.06-6.94 ((m, 7H), 6.13 (s, 1H), 5.37-5.35 (d, J=8Hz, 1H), 3.88-3.81 (m, 1H), 2.87 (s, 3H), 2.30 (s, 3H), 2.26 (s, 3H), 1.99-1.00 (m, 10H).Its ¹HNMR and MS data presentation are consistent with its chemical structure.

Embodiment 33: the synthetic and structure of compound ZX-3-18 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2,3-thiadiazoles-5-formic acid, to methyl Ortho-Chloro aniline and m-hydroxybenzaldehyde and each 3 mmole of cyclohexyl isonitrile, with reaction system stirring reaction at room temperature, desolventizing, (eluent is the sherwood oil of 60～90 degree: ethyl acetate) (volume ratio is 3: 1) gets pure product to use 200～300 order silica gel column chromatographies at last, yield: 3%, fusing point: 169-172 degree, HR MS (m/z): 521.1383 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 6.99-6.69 ((m, 7H), 6.17-6.07 (m, 2H), 5.50-5.48 (d, J=8Hz, 1H), 3.87-3.80 (m, 1H), 2.84 (s, 3H), 2.26 (s, 3H), 1.95-0.98 (m, 10H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 34: the synthetic and structure of compound ZX-3-19 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2,3-thiadiazoles-5-formic acid, to methyl Ortho-Chloro aniline and p-Hydroxybenzaldehyde and each 3 mmole of cyclohexyl isonitrile, with reaction system stirring reaction desolventizing at room temperature, (eluent is the sherwood oil of 60～90 degree: ethyl acetate) (volume ratio is 3: 1) gets pure product to use 200～300 order silica gel column chromatographies at last, yield: 40%, fusing point: 135-139 degree, HR MS (m/z): 521.1387 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 6.97-6.69 ((m, 8H), 6.05 (s, 1H), 5.58-5.56 (d, J=8Hz, 1H), 3.86-3.78 (m, 1H), 2.82 (s, 3H), 2.26 (s, 3H), 1.95-1.01 (m, 10H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 35: the synthetic and structure of compound ZX-4-1 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2,3-thiadiazoles-5-formic acid, to the adjacent fluoroaniline of methyl and phenyl aldehyde and each 2 mmole of cyclohexyl isonitrile, with reaction system at room temperature stirring reaction slowly separate out crystal, methyl alcohol wash product, yield: 52%, fusing point: 183-185 degree, HR MS (m/z): 489.1470 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.28-6.87 (m, 9H), 6.19 (s, 1H), 5.39-5.37 (d, J=8Hz, 1H), 3.93-3.84 (m, 1H), 2.86 (s, 3H), 2.15-2.15 (d, J=2Hz, 1H), 1.99-1.00 (m, 10H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 36: the synthetic and structure of compound ZX-4-2 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2,3-thiadiazoles-5-formic acid, to the adjacent fluoroaniline of methyl and o-chlorobenzaldehyde and each 2 mmole of cyclohexyl isonitrile, with reaction system at room temperature stirring reaction slowly separate out crystal, methyl alcohol wash product, yield: 22%, fusing point: 171-174 degree, HR MS (m/z): 523.1344 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.37-6.85 (m, 7H), 6.58 (s, 1H), 5.51-5.50 (d, J=6Hz, 1H), 3.93-3.84 (m, 1H), 2.86 (s, 3H), 2.11-2.11 (d, J=2Hz, 1H), 2.04-1.03 (m, 10H).Its ¹H NMR data presentation is consistent with its chemical structure.

Embodiment 37: the synthetic and structure of compound ZX-4-3 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid again, 2,3-thiadiazoles-5-formic acid, to the adjacent fluoroaniline of methyl and m chlorobenzaldehyde and each 2 mmole of cyclohexyl isonitrile, reaction system was separated out white solid in 5 minutes in stirring at room reaction, methyl alcohol wash product, yield: 81%, fusing point: 200-201 degree, HR MS (m/z): 523.1347 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.21-6.93 (m, 7H), 6.11 (s, 1H), 5.44-5.42 (d, J=8Hz, 1H), 3.88-3.83 (m, 1H), 2.88 (s, 3H), 2.18-2.18 (d, J=2Hz, 1H), 2.00-1.03 (m, 10H).Its ¹H NMR data presentation is consistent with its chemical structure.

Embodiment 38: the synthetic and structure of compound ZX-4-4 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid again, 2,3-thiadiazoles-5-formic acid, to the adjacent fluoroaniline of methyl and 4-chloro-benzaldehyde and each 2 mmole of cyclohexyl isonitrile, with reaction system at room temperature stirring reaction separated out white solid in 5 minutes, methyl alcohol wash product, yield: 78%, fusing point: 223-225 degree, HR MS (m/z): 523.1341 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.23-6.91 (m, 7H), 6.13 (s, 1H), 5.40-5.38 (d, J=8Hz, 1H), 3.88-3.81 (m, 1H), 2.87 (s, 3H), 2.18-2.18 (d, J=2Hz, 1H), 2.00-1.01 (m, 10H).Its ¹H NMR data presentation is consistent with its chemical structure.

Embodiment 39: the synthetic and structure of compound ZX-4-5 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2,3-thiadiazoles-5-formic acid, to the adjacent fluoroaniline of methyl and adjacent fluorobenzaldehyde and each 2 mmole of cyclohexyl isonitrile, with reaction system stirring reaction after 5 hours at room temperature, desolventizing, (eluent is the sherwood oil of 60～90 degree: ethyl acetate) (volume ratio is 3: 1) gets pure product to use 200～300 order silica gel column chromatographies at last, yield: 62%, fusing point: 139-141 degree, HR MS (m/z): 507.1642 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.28-6.89 (m, 7H), 6.45 (s, 1H), 5.55-5.53 (d, J=8Hz, 1H), 3.93-3.83 (m, 1H), 2.86 (s, 3H), 2.14-2.13 (d, J=2Hz, 1H), 2.03-1.04 (m, 10H).Its ¹H NMR data presentation is consistent with its chemical structure.

Embodiment 40: the synthetic and structure of compound ZX-4-6 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2,3-thiadiazoles-5-formic acid, to the adjacent fluoroaniline of methyl and a fluorobenzaldehyde and each 2 mmole of cyclohexyl isonitrile, with reaction system at room temperature stirring reaction separated out white solid in 2 days, methyl alcohol wash product, yield: 75%, fusing point: 223-225 degree, HR MS (m/z): 507.1639 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.24-6.90 (m, 7H), 6.12 (s, 1H), 5.44-5.42 (d, J=8Hz, 1H), 3.89-3.82 (m, 1H), 2.88 (s, 3H), 2.18-2.17 (d, J=2Hz, 1H), 2.01-1.03 (m, 10H).Its ¹The HNMR data presentation is consistent with its chemical structure.

Embodiment 41: the synthetic and structure of compound ZX-4-7 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2,3-thiadiazoles-5-formic acid, to the adjacent fluoroaniline of methyl and p-Fluorobenzenecarboxaldehyde and each 2 mmole of cyclohexyl isonitrile, with reaction system at room temperature stirring reaction separated out white solid in 2 days, methyl alcohol wash product, yield: 78%, fusing point: 204-206 degree, HR MS (m/z): 507.1640 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.16-6.91 (m, 7H), 6.16 (s, 1H), 5.41-5.39 (d, J=8Hz, 1H), 3.88-3.83 (m, 1H), 2.87 (s, 3H), 2.18-2.17 (d, J=2Hz, 1H), 2.00-1.01 (m, 10H).Its ¹H NMR data presentation is consistent with its chemical structure.

Embodiment 42: the synthetic and structure of compound ZX-4-8 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2,3-thiadiazoles-5-formic acid, to the adjacent fluoroaniline of methyl and 2-(Trifluoromethyl) benzaldehyde and each 2 mmole of cyclohexyl isonitrile, with reaction system at room temperature stirring reaction separated out white solid in 2 days, methyl alcohol wash product, yield: 52%, fusing point: 167-169 degree, HR MS (m/z): 557.1606 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.70-6.87 (m, 7H), 6.58 (s, 1H), 5.29-5.27 (d, J=8Hz, 1H), 3.87-3.80 (m, 1H), 2.85 (s, 3H), 2.13-2.13 (d, J=2Hz, 1H), 2.04-0.96 (m, 10H).Its ¹H NMR data presentation is consistent with its chemical structure.

Embodiment 43: the synthetic and structure of compound ZX-4-9 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2,3-thiadiazoles-5-formic acid, to the adjacent fluoroaniline of methyl and m-trifluoromethyl phenyl aldehyde and each 2 mmole of cyclohexyl isonitrile, with reaction system stirring reaction after 5 hours at room temperature, desolventizing, (eluent is the sherwood oil of 60～90 degree: ethyl acetate: methylene dichloride) (volume ratio is 10: 3: 3) gets pure product to use 200～300 order silica gel column chromatographies at last, yield: 46%, fusing point: 168-170 degree, HR MS (m/z): 557.1612 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.54-6.93 (m, 7H), 6.22 (s, 1H), 5.48-5.46 (d, J=8Hz, 1H), 3.90-3.83 (m, 1H), 2.89 (s, 3H), 2.16-2.16 (d, J=2Hz, 1H), 2.01-1.02 (m, 10H).Its ¹H NMR data presentation is consistent with its chemical structure.

Embodiment 44: the synthetic and structure of compound ZX-4-10 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2,3-thiadiazoles-5-formic acid, to the adjacent fluoroaniline of methyl with to trifluoromethylated benzaldehyde and each 2 mmole of cyclohexyl isonitrile, with reaction system stirring reaction after 5 hours at room temperature, desolventizing, (eluent is the sherwood oil of 60～90 degree: ethyl acetate: methylene dichloride) (volume ratio is 10: 3: 3) gets pure product to use 200～300 order silica gel column chromatographies at last, yield: 58%, fusing point: 224-226 degree, HR MS (m/z): 557.1597 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.53-6.93 (m, 7H), 6.18 (s, 1H), 5.45-5.43 (d, J=8Hz, 1H), 3.89-3.82 (m, 1H), 2.88 (s, 3H), 2.18-2.18 (d, J=2Hz, 1H), 2.01-1.02 (m, 10H).Its ¹H NMR data presentation is consistent with its chemical structure.

Embodiment 45: the synthetic and structure of compound ZX-4-11 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2,3-thiadiazoles-5-formic acid, to the adjacent fluoroaniline of methyl and Ortho Nitro Benzaldehyde and each 2 mmole of cyclohexyl isonitrile, with reaction system at room temperature stirring reaction separate out white solid, methyl alcohol wash product, yield: 68%, fusing point: 187-189 degree, HR MS (m/z): 534.1577 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.93-6.87 (m, 7H), 6.63 (s, 1H), 5.60-5.58 (d, J=9Hz, 1H), 3.89-3.83 (m, 1H), 2.88 (s, 3H), 2.12-2.12 (d, J=2Hz, 1H), 2.04-1.02 (m, 10H).Its ¹H NMR data presentation is consistent with its chemical structure.

Embodiment 46: the synthetic and structure of compound ZX-4-12 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2,3-thiadiazoles-5-formic acid, to the adjacent fluoroaniline of methyl and m-nitrobenzaldehyde and each 2 mmole of cyclohexyl isonitrile, with reaction system at room temperature stirring reaction separate out white solid, methyl alcohol wash product, yield: 90%, fusing point: 217-219 degree, HR MS (m/z): 534.1586 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 8.15-6.96 (m, 7H), 6.23 (s, 1H), 5.61-5.59 (d, J=8Hz, 1H), 3.91-3.83 (m, 1H), 2.89 (s, 3H), 2.17-2.17 (d, J=2Hz, 1H), 2.04-1.05 (m, 10H).Its ¹H NMR data presentation is consistent with its chemical structure.

Embodiment 47: the synthetic and structure of compound ZX-4-13 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2,3-thiadiazoles-5-formic acid, to the adjacent fluoroaniline of methyl and paranitrobenzaldehyde and each 2 mmole of cyclohexyl isonitrile, with reaction system at room temperature stirring reaction separate out white solid, methyl alcohol wash product, yield: 71%, fusing point: 231-233 degree, HR MS (m/z): 534.1586 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 8.12-6.97 (m, 7H), 6.21 (s, 1H), 5.55-5.53 (d, J=8Hz, 1H), 3.91-3.84 (m, 1H), 2.89 (s, 3H), 2.20-2.19 (d, J=2Hz, 1H), 2.04-1.05 (m, 10H).Its ¹H NMR data presentation is consistent with its chemical structure.

Embodiment 48: the synthetic and structure of compound ZX-4-14 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2,3-thiadiazoles-5-formic acid, to the adjacent fluoroaniline of methyl and o-methyl-benzene formaldehyde and each 2 mmole of cyclohexyl isonitrile, with reaction system at room temperature stirring reaction separate out white solid, methyl alcohol wash product, yield: 62%, fusing point: 170-172 degree, HR MS (m/z): 503.1882 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.19-6.81 (m, 7H), 6.52 (s, 1H), 5.32-5.30 (d, J=8Hz, 1H), 3.92-3.84 (m, 1H), 2.88 (s, 3H), 2.43 (s, 3H), 2.12-2.12 (d, J=1Hz, 1H), 2.00-1.00 (m, 10H).Its ¹H NMR data presentation is consistent with its chemical structure.

Embodiment 49: the synthetic and structure of compound ZX-4-15 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2,3-thiadiazoles-5-formic acid, to the adjacent fluoroaniline of methyl and a tolyl aldehyde and each 2 mmole of cyclohexyl isonitrile, with reaction system at room temperature stirring reaction separate out white solid, methyl alcohol wash product, yield: 62%, fusing point: 209-211 degree, HR MS (m/z): 503.1881 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.13-6.89 (m, 7H), 6.15 (s, 1H), 5.39-5.37 (d, J=8Hz, 1H), 3.89-3.82 (m, 1H), 2.88 (s, 3H), 2.25 (s, 3H), 2.16-2.16 (d, J=2Hz, 1H), 1.98-1.00 (m, 10H).Its ¹H NMR data presentation is consistent with its chemical structure.

Embodiment 50: the synthetic and structure of compound ZX-4-16 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2,3-thiadiazoles-5-formic acid, to the adjacent fluoroaniline of methyl and p-tolyl aldehyde and each 2 mmole of cyclohexyl isonitrile, with reaction system at room temperature stirring reaction separate out white solid, methyl alcohol wash product, yield: 84%, fusing point: 178-180 degree, HR MS (m/z): 503.1887 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.02-6.88 (m, 7H), 6.15 (s, 1H), 5.36-5.34 (d, J=8Hz, 1H), 3.88-3.81 (m, 1H), 2.87 (s, 3H), 2.30 (s, 3H), 2.16-2.16 (d, J=2Hz, 1H), 1.97-0.99 (m, 10H).Its ¹H NMR data presentation is consistent with its chemical structure.

Embodiment 51: the synthetic and structure of compound ZX-4-17 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2,3-thiadiazoles-5-formic acid, to the adjacent fluoroaniline of methyl and p-Hydroxybenzaldehyde and each 2 mmole of cyclohexyl isonitrile, with reaction system at room temperature stirring reaction separate out white solid, methyl alcohol wash product, yield: 79%, fusing point: 171-174 degree, HR MS (m/z): 505.1672 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.02-6.67 (m, 7H), 6.13 (s, 1H), 5.39-5.37 (d, J=9Hz, 1H), 5.04 (s, 1H), 3.88-3.81 (m, 1H), 2.87 (s, 3H), 2.17-2.16 (d, J=2Hz, 1H), 1.98-1.01 (m, 10H).Its ¹H NMR data presentation is consistent with its chemical structure.

Embodiment 52: the synthetic and structure of compound ZX-5-1 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid again, 2,3-thiadiazoles-5-formic acid, to the adjacent fluoroaniline of methyl and phenyl aldehyde and each 3 mmole of sec.-propyl isonitrile, system is separated out solid in the stirring at room reaction, and methanol wash gets product, yield: 43%, fusing point: 144-146 degree, HR MS (m/z): 449.1424 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.30-6.88 (m, 8H), 6.17 (s, 1H), 5.34-5.32 (d, J=8Hz, 1H), 4.22-4.12 (m, 1H), 2.88 (s, 3H), 2.16-2.15 (d, J=2Hz, 3H), and 1.19-1.18 (d, J=7Hz, 3H), 1.11-1.09 (d, J=7Hz, 3H).Its ¹HNMR and MS data presentation are consistent with its chemical structure.

Embodiment 53: the synthetic and structure of compound ZX-5-2 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid again, 2,3-thiadiazoles-5-formic acid, to the adjacent fluoroaniline of methyl and o-chlorobenzaldehyde and each 3 mmole of sec.-propyl isonitrile, reaction system is reacted in stirring at room, behind the desolventizing with 200～300 order silica gel column chromatographies (eluent be 60～90 the degree sherwood oils: ethyl acetate) (volume ratio is 3: 1) pure product, yield: 54%, HR MS (m/z): 461.1206 (M+1); Fusing point: the 166-168 degree, ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.37-6.85 (m, 7H), 6.58 (s, 1H), 5.51-5.49 (d, J=7Hz, 1H), 4.25-4.14 (m, 1H), 2.86 (s, 3H), 2.11-2.11 (d, J=1Hz, 3H), and 1.24-1.22 (d, J=7Hz, 3H), 1.11-1.09 (d, J=6Hz, 3H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 54: the synthetic and structure of compound ZX-5-3 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2,3-thiadiazoles-5-formic acid, to the adjacent fluoroaniline of methyl and m chlorobenzaldehyde and each 3 mmole of sec.-propyl isonitrile, with reaction system at room temperature stirring reaction separate out solid, methanol wash gets product, yield: 45%, fusing point: 169-172 degree, HR MS (m/z): 461.1209 (M+1); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.27-6.93 (m, 7H), 6.08 (s, 1H), 5.40-5.38 (d, J=8Hz, 1H), 4.21-4.12 (m, 1H), 2.88 (s, 3H), 2.18-2.18 (d, J=2Hz, 3H), and 1.21-1.19 (d, J=7Hz, 3H), 1.12-1.11 (d, J=7Hz, 3H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 55: the synthetic and structure of compound ZX-5-4 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid again, 2,3-thiadiazoles-5-formic acid, to the adjacent fluoroaniline of methyl and 4-chloro-benzaldehyde and each 3 mmole of sec.-propyl isonitrile, reaction system at room temperature stirring reaction is separated out solid, and methanol wash gets product, yield: 70%, fusing point: 176-178 degree, HR MS (m/z): 461.1210 (M+1); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.24-6.92 (m, 7H), 6.11 (s, 1H), 5.36-5.34 (d, J=7Hz, 1H), 4.23-4.11 (m, 1H), 2.87 (s, 3H), 2.18 (s, 3H), 1.20-1.19 (d, J=6Hz, 3H), 1.11-1.10 (d, J=7Hz, 3H).Its ¹HNMR and MS data presentation are consistent with its chemical structure.

Embodiment 56: the synthetic and structure of compound ZX-5-5 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2,3-thiadiazoles-5-formic acid, to the adjacent fluoroaniline of methyl and adjacent fluorobenzaldehyde and each 3 mmole of sec.-propyl isonitrile, with reaction system at room temperature stirring reaction separate out solid, get product with methanol wash, yield: 40%, HR MS (m/z): 445.1507 (M+1); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.23-6.89 (m, 7H), 6.44 (s, 1H), 5.50-5.48 (d, J=6Hz, 1H), 4.22-4.17 (m, 1H), 2.87 (s, 3H), 2.14-2.14 (d, J=2Hz, 3H), and 1.24-1.23 (d, J=7Hz, 3H), 1.14-1.13 (d, J=7Hz, 3H).Its ¹HNMR and MS data presentation are consistent with its chemical structure.

Embodiment 57: the synthetic and structure of compound ZX-5-6 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid again, 2,3-thiadiazoles-5-formic acid, to the adjacent fluoroaniline of methyl and a fluorobenzaldehyde and each 3 mmole of sec.-propyl isonitrile, with reaction system at room temperature stirring reaction separate out solid, get product with methanol wash, fusing point: 163-165 degree, HR MS (m/z): 445.1505 (M+1); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.23-6.89 (m, 7H), 6.10 (s, 1H), 5.41-5.39 (d, J=7Hz, 1H), 4.19-4.13 (m, 1H), 2.88 (s, 3H), 2.18-2.17 (d, J=2Hz, 3H), and 1.21-1.19 (d, J=7Hz, 3H), 1.12-1.11 (d, J=7Hz, 3H).Its ¹HNMR and MS data presentation are consistent with its chemical structure.

Embodiment 58: the synthetic and structure of compound ZX-5-7 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid again, 2,3-thiadiazoles-5-formic acid, to the adjacent fluoroaniline of methyl and p-Fluorobenzenecarboxaldehyde and each 3 mmole of sec.-propyl isonitrile, reaction system is separated out solid in the stirring at room reaction, and methanol wash gets product, yield: 71%, fusing point: 179-182 degree, HR MS (m/z): 445.1511 (M+1); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.16-6.91 (m, 7H), 6.14 (s, 1H), 5.36-5.34 (d, J=7Hz, 1H), 4.22-4.11 (m, 1H), 2.88 (s, 3H), 2.18-2.17 (d, J=2Hz, 3H), and 1.21-1.19 (d, J=7Hz, 3H), 1.14-1.10 (d, J=7Hz, 3H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 59: the synthetic and structure of compound ZX-5-8 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid again, 2,3-thiadiazoles-5-formic acid, to the adjacent fluoroaniline of methyl and 2-(Trifluoromethyl) benzaldehyde and each 3 mmole of sec.-propyl isonitrile, reaction system is reacted in stirring at room, behind the desolventizing with 200～300 order silica gel column chromatographies (eluent be 60～90 the degree sherwood oils: ethyl acetate) (volume ratio is 3: 1) pure product, yield: 46%, HR MS (m/z): 495.1476 (M+1); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.71-6.90 (m, 7H), 6.57 (s, 1H), 5.25-5.23 (d, J=8Hz, 1H), 4.16-4.11 (m, 1H), 2.86 (s, 3H), 2.14-2.13 (d, J=2Hz, 3H), and 1.23-1.21 (d, J=7Hz, 3H), 1.07-1.05 (d, J=7Hz, 3H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 60: the synthetic and structure of compound ZX-5-9 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid again, 2,3-thiadiazoles-5-formic acid, to the adjacent fluoroaniline of methyl and m-trifluoromethyl phenyl aldehyde and each 3 mmole of sec.-propyl isonitrile, reaction system is separated out solid in the stirring at room reaction, and methanol wash gets product, yield: 48%, fusing point: 184-188 degree, HR MS (m/z): 495.1473 (M+1); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.54-6.93 (m, 7H), 6.20 (s, 1H), 5.43-5.41 (d, J=8Hz, 1H), 4.20-4.13 (m, 1H), 2.89 (s, 3H), 2.17-2.16 (d, J=2Hz, 3H), and 1.22-1.21 (d, J=7Hz, 3H), 1.12-1.10 (d, J=7Hz, 3H).Its ¹H NMR is consistent with its chemical structure with the MS data presentation.

Embodiment 61: the synthetic and structure of compound ZX-5-10 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid again, 2,3-thiadiazoles-5-formic acid, to the adjacent fluoroaniline of methyl with to trifluoromethylated benzaldehyde and each 3 mmole of sec.-propyl isonitrile, reaction system is separated out solid in the stirring at room reaction, and methanol wash gets product, yield: 58%, fusing point: 196-198 degree, HR MS (m/z): 495.1477 (M+1); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.53-6.92 (m, 7H), 6.16 (s, 1H), 5.41-5.39 (d, J=8Hz, 1H), 4.23-4.14 (m, 1H), 2.88 (s, 3H), 2.18-2.18 (d, J=2Hz, 3H), and 1.22-1.20 (d, J=7Hz, 3H), 1.13-1.11 (d, J=7Hz, 3H).Its ¹H NMR is consistent with its chemical structure with the MS data presentation.

Embodiment 62: the synthetic and structure of compound ZX-5-11 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid again, 2,3-thiadiazoles-5-formic acid, to the adjacent fluoroaniline of methyl and Ortho Nitro Benzaldehyde and each 3 mmole of sec.-propyl isonitrile, reaction system is reacted in stirring at room, behind the desolventizing with 200～300 order silica gel column chromatographies (eluent be 60～90 the degree sherwood oils: ethyl acetate) (volume ratio is 3: 1) pure product, yield: 37%, HR MS (m/z): 494.1267 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.93-6.87 (m, 7H), 6.63 (s, 1H), 5.66-5.64 (d, J=7Hz, 1H), 4.15-4.09 (m, 1H), 2.87 (s, 3H), 2.12-2.12 (d, J=2Hz, 3H), and 1.23-1.22 (d, J=7Hz, 3H), 1.11-1.10 (d, J=7Hz, 3H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 63: the synthetic and structure of compound ZX-5-12 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid again, 2,3-thiadiazoles-5-formic acid, to the adjacent fluoroaniline of methyl and m-nitrobenzaldehyde and each 3 mmole of sec.-propyl isonitrile, reaction system is reacted in stirring at room, behind the desolventizing with 200～300 order silica gel column chromatographies (eluent be 60～90 the degree sherwood oils: ethyl acetate) (volume ratio is 3: 1) pure product, yield: 99%, HR MS (m/z): 494.1268 (M+23); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 8.16-6.96 (m, 7H), 6.21 (s, 1H), 5.57-5.55 (d, J=8Hz, 1H), 4.21-4.16 (m, 1H), 2.90 (s, 3H), 2.18-2.18 (d, J=2Hz, 3H), and 1.24-1.23 (d, J=7Hz, 3H), 1.15-1.13 (d, J=7Hz, 3H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 64: the synthetic and structure of compound ZX-5-13 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2,3-thiadiazoles-5-formic acid, to the adjacent fluoroaniline of methyl and paranitrobenzaldehyde and each 3 mmole of sec.-propyl isonitrile, reaction system is reacted in stirring at room, behind the desolventizing with 200～300 order silica gel column chromatographies (eluent be 60～90 the degree sherwood oils: ethyl acetate) (volume ratio is 3: 1) pure product, yield: 13%, HR MS (m/z): 472.1446 (M+1); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 8.12-6.72 (m, 7H), 6.18 (s, 1H), 5.50-5.48 (d, J=8Hz, 1H), 4.22-4.13 (m, 1H), 2.89 (s, 3H), 2.19-2.19 (d, J=2Hz, 3H), and 1.24-1.22 (d, J=7Hz, 3H), 1.14-1.12 (d, J=7Hz, 3H.Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 65: the synthetic and structure of compound ZX-5-14 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2,3-thiadiazoles-5-formic acid, to the adjacent fluoroaniline of methyl and o-methyl-benzene formaldehyde and each 3 mmole of sec.-propyl isonitrile, with the reaction of reaction system stirring at room, (eluent is the sherwood oil of 60～90 degree: ethyl acetate) (volume ratio is 3: 1) gets pure product, yield: 49% with 200～300 order silica gel column chromatographies behind the desolventizing, fusing point: 136-139 degree, HR MS (m/z): 441.1757 (M+1); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.19-6.81 (m, 7H), 6.51 (s, 1H), 5.27-5.25 (m, 1H), 4.22-4.17 (m, 1H), 2.88 (s, 3H), 2.43 (s, 3H), 2.13-2.12 (d, J=2Hz, 3H), and 1.20-1.19 (d, J=7Hz, 3H), 1.13-1.11 (d, J=6Hz, 3H).Its ¹HNMR and MS data presentation are consistent with its chemical structure.

Embodiment 66: the synthetic and structure of compound ZX-5-15 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2,3-thiadiazoles-5-formic acid, to the adjacent fluoroaniline of methyl and a tolyl aldehyde and each 3 mmole of sec.-propyl isonitrile, reaction system is reacted in stirring at room, behind the desolventizing with 200～300 order silica gel column chromatographies (eluent be 60～90 the degree sherwood oils: ethyl acetate) (volume ratio is 3: 1) pure product, yield: 19%, HR MS (m/z): 441.1758 (M+1); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.13-6.88 (m, 7H), 6.13 (s, 1H), and 5.32-5.30 (d, J=9Hz, 1H), 4.19-4.17 (m, 1H), 2.88 (s, 3H), 2.26 (s, 3H), 2.16-2.16 (d, J=2Hz, 3H), and 1.19-1.17 (d, J=6Hz, 3H), 1.11-1.09 (d, J=7Hz, 3H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 67: the synthetic and structure of compound ZX-5-16 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid again, 2,3-thiadiazoles-5-formic acid, to the adjacent fluoroaniline of methyl and p-tolyl aldehyde and each 3 mmole of sec.-propyl isonitrile, reaction system is separated out solid in the stirring at room reaction, gets product with methanol wash, yield: 54%, fusing point: 170-172 degree, HR MS (m/z): 441.1757 (M+1); ¹H NMR (solvent: CDCl ₃, chemical shift): 7.04-6.89 (m, 7H), 6.14 (s, 1H), 5.32-5.30 (d, J=7Hz, 1H), 4.20-4.11 (m, 1H), 2.87 (s, 3H), 2.30 (s, 3H), 2.16 (s, 3H), and 1.18-1.16 (d, J=6Hz, 3H), 1.10-1.09 (d, J=6Hz, 3H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 68: the synthetic and structure of compound ZX-5-17 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid then, 2,3-thiadiazoles-5-formic acid, to the adjacent fluoroaniline of methyl and m-hydroxybenzaldehyde and each 3 mmole of sec.-propyl isonitrile, with reaction system stirring reaction at room temperature, desolventizing, use at last 200～300 order silica gel column chromatographies (eluent is the sherwood oils of 60～90 degree: ethyl acetate) (volume ratio is 3: 1) pure product, yield: 48%, HR MS (m/z): 443.1550 (M+1); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.11-6.64 (m, 7H), 6.27 (s, 1H), 6.03 (s, 1H), 5.58-5.56 (d, J=9Hz, 1H), 4.18-4.10 (m, 1H), 2.83 (s, 3H), 2.16-2,16 (d, J=2Hz, 3H), 1.18-1.16 (d, J=7Hz, 3H), and 1.10-1.08 (d, J=7Hz, 3H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 69: the synthetic and structure of compound ZX-5-18 is identified

In 50 milliliters of round-bottomed flasks, add 10ml methyl alcohol, add own synthetic 4-methyl isophthalic acid again, 2,3-thiadiazoles-5-formic acid, to the adjacent fluoroaniline of methyl and p-Hydroxybenzaldehyde and each 3 mmole of sec.-propyl isonitrile with reaction system stirring reaction at room temperature, desolventizing, (eluent is the sherwood oil of 60～90 degree: ethyl acetate) (volume ratio is 3: 1) gets pure product, yield: 48% to use 200～300 order silica gel column chromatographies at last, fusing point: 159-162 degree, HR MS (m/z): 443.1554 (M+1); ¹H NMR (solvent: CDCl ₃, chemical shift): δ 7.01-6.68 (m, 7H), 6.211 (s, 1H), 5.36-5.32 (m, 2H), 4.19-4.11 (m, 1H), 2.87 (s, 3H), 2.17-2,17 (d, J=2Hz, 3H), and 1.19-1.17 (d, J=7Hz, 3H), 1.11-1.09 (d, J=7Hz, 3H).Its ¹H NMR and MS data presentation are consistent with its chemical structure.

Embodiment 70: 4-methyl isophthalic acid of the present invention, and 2, the bacteriostatic activity of 3-thiadiazoles derivative:

The measuring method part seen in the title and the code name of the frequently seen plants pathogenic fungi of the present invention test, and these bacterial classifications can be represented the kind of most of pathogenic bacteria that agriculture field and field, gardening field in the agriculture production or protection ground takes place.Thalli growth rate method measurement result sees Table 2, table 2 shows, synthetic part of compounds of the present invention has bacteriostatic action in various degree to the growth of the part pathogenic fungi of mensuration: when 50 mcg/ml, ZX-2-7, ZX-2-8, ZX-3-4 and ZX-4-9 to the inhibiting rate of PS more than or equal to 50%, ZX-3-14, ZX-3-18, ZX-3-19 and ZX-4-9 to the inhibiting rate of AS more than or equal to 50%, ZX-3-1, ZX-3-10, ZX-3-12, ZX-3-19 and ZX-4-9, ZX-4-12, ZX-4-14 to the inhibiting rate of CA greater than 50%, majority of compounds such as ZX-2-5, ZX-2-10, ZX-2-15, ZX-3-1, ZX-3-2, ZX-3-3, ZX-3-6, ZX-3-7, ZX-3-8, ZX-3-15, ZX-3-16, ZX-4-9, ZX-4-14, ZX-5-9, ZX-5-18 to the inhibiting rate of RS more than or equal to 50%, ZX-2-3 and ZX-3-16 and ZX-4-14 to the inhibiting rate of PO more than or equal to 50%, ZX-4-8, ZX-4-10, ZX-4-11, ZX-4-14 to the inhibiting rate of CB more than or equal to 50%, ZX-4-7 and ZX-4-8 to the inhibiting rate of PI more than or equal to 50%, ZX-4-9 is to GZ, PP and CL also have excellent bactericidal activity, and inhibiting rate is greater than 60%.The bacteriostatic activity of majority of compounds is all greater than the commercial TDL of positive control medicament.In the patent that we apply in earlier stage (CN101250167A) the synthetic compound only ZX-U-17 be 53.33% to the activity of CA, ZX-U-22 is 62.86% to the activity of BC, other compounds do not have bacteriostatic activity, the present invention has carried out simultaneous test to these two compounds once more, found that, the bacteriostatic activity of synthetic part of compounds of the present invention in contrast because the introducing of phenyl and substituted-phenyl, its bacteriostatic activity have increased significantly (seeing Table 2).

Compound I of the present invention is mixed to use with in the following sterilant one or more and is had synergy or summation action: white urea cyanogen, thiram, ziram, zinc manganese ethylenebisdithiocarbamate, phosethyl Al, thiophanate_methyl, m-tetrachlorophthalodinitrile, the enemy can be loose, derosal, procymidone, RP-26019, Vancide 89, the mould prestige of second, ester bacterium urea, fultolanil, F-1991, cyproconazole, methasulfocarb, fenpropidin, dislike acid amides, triazolone, thiophanate methyl, metaxanin, Metalaxyl-M, M 9834, hymexazol, dimethomorph, flumorph, tridemorph, fluzilazol, alkene azoles alcohol, tebuconazole, dislike mould spirit, Difenoconazole, mepanipyrim, Azoxystrobin, Wocosin 50TK, diazosulfide, Whitfield's ointment, tiadinil, tisocromide, N-(5-methyl-1,3-thiazole-2-yl)-4-methyl-1,2,3-thiadiazole etc., these compositions can be used for the control of agricultural plants disease and gardening plant disease, controlling object comprises the Achyla of Oomycete, Aphanomyces, pythium, phytophthora, Sclerospora, Plasmopara, false Peronospora, a disease that genus produces surplus the Peronospora etc. 20, as seedling blight of rice, the tomato root rot, the late blight of potato, black shank, the millet Powdery Mildew, downy mildew of garpe, downy mildew of lettuce, other diseases of plurality of cereals crops such as cucumber downy mildew and cash crop etc., the formulation of using can be a wettable powder, sustained release dosage, pulvis, micro-capsule suspension, can disperse dense dose, seed treatment emulsion, aqueous emulsion, big granula, granule, microemulsion, oil-suspending agent, finish, seed with coated pesticidal, suspension concentrates, suspended emulsion agent, water-soluble granule, soluble thick agent, water-dispersible granules or the like, the ratio of Compound I of the present invention in composition can be that weight ratio is 1%-90%, the prevention effect of medicament is good, these compositions have certain synergism and summation action, do not find to have the composition of antagonistic action.

Embodiment 71: 4-methyl isophthalic acid of the present invention, and 2, the anti-phytoviral activity of 3-thiadiazoles derivative:

Synthetic majority of compounds of the present invention has good inhibitory effect to the growth of tobacco mosaic virus (TMV), measurement result sees Table 3: when 500 mcg/ml and 100 mcg/ml, the withered spot method of half leaf records compound ZX-2-8, ZX-2-10, ZX-2-11, ZX-2-17, ZX-3-16, ZX-4-7, ZX-4-8, ZX-4-9, ZX-4-12, ZX-4-13, ZX-4-14, ZX-4-16, ZX-4-17 and ZX-5-1, ZX-5-3, ZX-5-4, ZX-5-5, ZX-5-6, ZX-5-8, ZX-5-9, ZX-5-10, ZX-5-11, ZX-5-12, ZX-5-14, ZX-5-16 to the activity of TMV and positive control medicament virazole or TDL quite or be higher than virazole or TDL.Measurement result to part of compounds provide protection and therapeutic action and inducing action sees Table 4.Table 4 shows: ZX-2-8, ZX-2-11, ZX-4-1, ZX-4-8, ZX-4-9, ZX-4-12, ZX-4-17 and ZX-5-6, the existing good protection activity of ZX-5-14, ZX-5-16 have the fine effect of inducing again; its activity all is higher than corresponding positive control medicament virazole or TDL; as can be seen; BTH has good protection and treatment and induced activity, and Ningnanmycin also has good protection and treatment and induces effect.The compound of the serial ZX-5 that has measured has good therapeutic activity, and its activity is apparently higher than positive control medicament virazole.The middle synthetic compound of patent in early stage (CN101250167A) only ZX-U23 has induced activity preferably; the present invention once more under identical conditions in detail comparative study the biological activity of this compound; found that; ZX-U23 is active very poor to the withered spot method of TMV half leaf; and do not protect activity and therapeutic activity; only has induced activity; its induced activity and positive control medicament TDL be (table 4) quite; therefore, the direct antiviral activity of the most of heart compound of synthetic of the present invention has obtained significant raising as protecting activity and therapeutic activity and induced activity because of the introducing of phenyl or substituted-phenyl.

The result of preliminary biological assay test shows, all 4-methyl isophthalic acids of the present invention, 2,3-thiadiazoles derivative and existing Antiphytoviral medicament such as diazosulfide, Whitfield's ointment, tiadinil, tisocromide, N-(5-methyl-1,3-thiazole-2-yl)-4-methyl-1,2,3-thiadiazole and 4-methyl isophthalic acid, 2,3-thiadiazoles-5-formic acid, the 4-methyl isophthalic acid, 2,3-thiadiazoles-5-ethyl formate, the DL-beta-aminobutyric acid, virazole, Ningnanmycin, antofine, virus star and XY-13, in other known any medicament that can be used as Antiphytoviral such as XY-30 any one or two kinds are used in combination the control that can be used for agricultural plants and gardening plant virus disease, and controlling object comprises tobacco, tomato, vegetables, melon, fruit, the tobacco mosaic virus disease of grain and legume crop etc., the cucumber mosaic virus viral disease, tomato virus disease, the sweet potato viruses disease, pepper virus disease, potato virus disease, melon virus disease and corn short mosaic disease etc.The formulation of using can be a wettable powder, sustained release dosage, pulvis, micro-capsule suspension, can disperse dense dose, seed treatment emulsion, aqueous emulsion, big granula, granule, microemulsion, oil-suspending agent, finish, seed with coated pesticidal, suspension concentrates, suspended emulsion agent, water-soluble granule, soluble thick agent, water-dispersible granules or the like, 4-methyl isophthalic acid of the present invention, 2, the ratio of 3-thiadiazoles derivative in composition can be that weight ratio is 1%-90%, the prevention effect ideal of medicament, these compositions have certain synergism and summation action, do not find to have the composition of antagonistic action.

Embodiment 72: 4-methyl isophthalic acid of the present invention, 2, the working method of 3-thiadiazoles derivative and common compounded preparation of pesticide and stability

4-methyl isophthalic acid of the present invention, 2, the mixed preparation working method of 3-thiadiazoles derivative and common agricultural chemicals sees Table 5, table 5 as seen, most medicament all can be processed according to the method for statement, the main component of liquid preparation is other a component of effective constituent and solubility promoter and tensio-active agent and synergistic agent and antifreezing agent etc., the composition of solid preparation mainly includes the effect composition, other components such as tensio-active agent and filler, preparation to processing carries out cold storage test, liquid preparation is placed 1 week not have to precipitate at 0 ± 2 degree and is separated out, solid preparation placed for 2 weeks at 54 ± 2 degree, caking phenomenon does not appear in medicament, the medicament drug effect that all preparations store before and after placing does not have significant difference, and the rate of decomposition of mixing effective constituent illustrates the medicament qualified stability in 5%.

Table 1 synthetic of the present invention contains the 4-methyl isophthalic acid, and 2, the chemical structure of 3-thiadiazoles Hete rocyclic derivatives

Table 1 synthetic of the present invention contains the 4-methyl isophthalic acid, and 2, the chemical structure (continuing) of 3-thiadiazoles Hete rocyclic derivatives

Table 2 synthetic of the present invention contains the 4-methyl isophthalic acid, and 2, the bacteriostatic activity of 3-thiadiazoles derivative (/ %) (concentration is 50 mcg/ml)

Compound	??CB	??FO	??CA	??AS	??GZ	??PP	??BC	??PO	??PS	??CL	??RS	??PI
													??ZX-2-2	??14.29	??20.93	??15.79	??8.33	??20.93	??16.13	??20.00	??ND	??0	??48.72	??ND	??0
??ZX-2-3	??16.67	??28.57	??9.09	??26.32	??ND	??8.77	??ND	??52.38	??25.77	??33.33	??36.67	??11.11
													??ZX-2-4	??16.67	??21.43	??0	??15.79	??ND	??8.77	??ND	??14.29	??21.65	??11.11	??36.67	??11.11
??ZX-2-5	??16.67	??21.43	??9.09	??31.58	??ND	??0	??ND	??33.33	??36.08	??22.22	??63.33	??11.11
													??ZX-2-6	??0	??21.43	??9.09	??21.05	??ND	??1.75	??ND	??4.76	??25.77	??22.22	??30.00	??11.11
??ZX-2-7	??14.30	??18.80	??26.70	??10.00	??5.30	??25.00	??44.40	??ND	??54.00	??25.00	??ND	??0
													??ZX-2-8	??28.60	??12.50	??46.70	??30.00	??5.30	??33.30	??44.40	??ND	??58.00	??ND	??ND	??7.70
??ZX-2-9	??16.67	??28.57	??9.09	??26.32	??ND	??8.77	??ND	??33.33	??46.39	??11.11	??36.67	??11.11
													??ZX-2-10	??16.67	??21.43	??0	??26.32	??ND	??8.77	??ND	??0	??5.15	??22.22	??63.33	??11.11
??ZX-2-11	??0	??ND	??42.86	??50.00	??11.54	??34.62	??ND	??14.29	??26.09	??26.32	??40.00	??41.18
													??ZX-2-12	??0	??ND	??28.57	??25.00	??26.92	??0	??ND	??14.29	??21.74	??31.58	??37.14	??35.29
??ZX-2-13	??16.67	??21.43	??9.09	??26.32	??ND	??8.77	??ND	??4.76	??25.77	??22.22	??46.67	??11.11
													??ZX-2-14	??16.67	??21.43	??9.09	??15.79	??ND	??0	??ND	??14.29	??36.08	??0	??30.00	??11.11

Compound	??CB	??FO	??CA	??AS	??GZ	??PP	??BC	??PO	??PS	??CL	??RS	??PI
													??ZX-2-15	??16.67	??21.43	??18.18	??31.58	??ND	??8.77	??ND	??42.86	??15.46	??33.33	??56.67	??27.78
??ZX-2-16	??16.67	??21.43	??9.09	??10.53	??ND	??8.77	??ND	??4.76	??5.15	??0	??36.67	??11.11
													??ZX-2-17	??16.67	??7.14	??9.09	??15.79	??ND	??8.77	??ND	??0	??15.46	??11.11	??43.33	??11.11
??ZX-3-1	??36.36	??25.00	??60.87	??31.58	??ND	??21.74	??ND	??40.00	??16.67	??9.09	??62.96	??32.35
													??ZX-3-2	??27.27	??0	??47.83	??26.32	??ND	??13.04	??ND	??40.00	??11.90	??4.55	??66.67	??26.47
??ZX-3-3	??18.18	??10.71	??39.13	??21.05	??ND	??26.09	??ND	??20.00	??11.90	??9.09	??64.81	??20.59
													??ZX-3-4	??0	??ND	??28.57	??37.50	??34.62	??26.92	??ND	??28.57	??50.00	??31.58	??40.00	??41.18
??ZX-3-5	??12.50	??ND	??42.86	??37.50	??46.15	??30.77	??ND	??14.29	??32.61	??47.37	??48.57	??35.29
													??ZX-3-6	??27.27	??21.43	??39.13	??21.05	??ND	??21.74	??ND	??15.00	??16.67	??9.09	??68.52	??20.59
??ZX-3-7	??27.27	??0	??26.09	??36.84	??ND	??26.09	??ND	??25.00	??11.90	??4.55	??66.67	??35.29
													??ZX-3-8	??0	??ND	??28.57	??37.50	??11.54	??46.15	??ND	??42.86	??32.61	??52.63	??60.00	??41.18
??ZX-3-9	??22.22	??31.25	??21.05	??32.35	??ND	??31.03	??ND	??23.53	??29.85	??20.00	??20.00	??20.00
													??ZX-3-10	??0	??ND	??57.14	??31.25	??19.23	??19.23	??ND	??14.29	??21.74	??15.79	??37.14	??29.41

Compound	??CB	??FO	??CA	??AS	??GZ	??PP	??BC	??PO	??PS	??CL	??RS	??PI
													??ZX-3-11	??11.11	??21.88	??15.79	??35.29	??ND	??41.38	??ND	??23.53	??22.39	??32.00	??28.57	??0

ND: undetermined

Table 2 synthetic of the present invention contains the 4-methyl isophthalic acid, and 2, the bacteriostatic activity of 3-thiadiazoles derivative (/ %) (concentration is 50 mcg/ml) (continuing)

Compound	??CB	??FO	??CA	??AS	??GZ	??PP	??BC	??PO	??PS	??CL	??RS	??PI
													??ZX-3-12	??0	??ND	??57.14	??37.50	??11.54	??19.23	??ND	??0	??19.57	??26.32	??40.00	??41.18
??ZX-3-13	??11.11	??21.88	??15.79	??35.29	??ND	??37.93	??ND	??17.65	??25.37	??24.00	??28.57	??12.00
													??ZX-3-14	??0	??ND	??14.29	??56.25	??23.08	??34.62	??ND	??0	??43.48	??36.84	??42.86	??35.29
??ZX-3-15	??27.27	??17.86	??17.39	??36.84	??ND	??34.78	??ND	??10.00	??23.81	??13.64	??62.92	??35.29
													??ZX-3-16	??27.27	??17.86	??34.78	??42.11	??ND	??26.09	??ND	??50.00	??23.81	??18.18	??68.52	??26.47
??ZX-3-18	??44.44	??34.38	??47.37	??55.88	??ND	??48.28	??ND	??29.41	??22.39	??44.00	??42.86	??24.00
													??ZX-3-19	??33.33	??37.50	??52.63	??50.00	??ND	??31.03	??ND	??41.18	??37.31	??8.00	??45.71	??32.00
??ZX-4-1	??33.33	??ND	??21.43	??0	??44.83	??0	??ND	??14.29	??0	??14.29	??27.91	??5.26
													??ZX-4-2	??0	??ND	??28.57	??18.75	??23.08	??30.77	??ND	??14.29	??21.74	??26.32	??37.14	??47.06
??ZX-4-3	??12.50	??ND	??14.29	??25.00	??26.92	??7.69	??ND	??28.57	??28.26	??15.79	??34.29	??29.41
													??ZX-4-4	??0	??ND	??0	??37.50	??11.54	??23.08	??ND	??42.86	??21.74	??36.84	??42.86	??23.53
??ZX-4-5	??0	??ND	??28.57	??37.50	??0	??30.77	??ND	??42.86	??32.61	??42.11	??48.57	??41.18
													??ZX-4-6	??16.67	??ND	??21.43	??0	??37.93	??0	??ND	??0	??0	??4.76	??41.86	??5.26

Compound	??CB	??FO	??CA	??AS	??GZ	??PP	??BC	??PO	??PS	??CL	??RS	??PI
													??ZX-4-7	??0	??ND	??42.86	??43.75	??7.69	??19.23	??ND	??14.29	??17.39	??26.32	??40.00	??29.41
??ZX-4-8	??75.00	??ND	??28.57	??43.75	??15.38	??23.08	??ND	??28.57	??10.87	??47.37	??37.14	??52.94
													??ZX-4-9	??0	??ND	??71.43	??100	??61.54	??84.62	??ND	??14.29	??73.91	??94.74	??97.14	??88.24
??ZX-4-10	??50.00	??ND	??57.14	??0	??24.14	??0	??ND	??14.29	??6.12	??4.76	??34.88	??0
													??ZX-4-11	??66.67	??ND	??21.43	??0	??41.38	??0	??ND	??0	??0	??4.76	??37.21	??5.26
??ZX-4-12	??33.33	??ND	??57.14	??0	??27.59	??31.91	??ND	??14.29	??44.90	??9.52	??30.23	??10.53
													??ZX-4-13	??16.67	??ND	??14.29	??0	??34.48	??0	??ND	??0	??0	??0	??39.53	??15.79
??ZX-4-14	??66.67	??ND	??78.57	??44.44	??34.48	??53.19	??ND	??57.14	??16.33	??42.86	??51.16	??47.37
													??ZX-4-15	??33.33	??ND	??21.43	??0	??34.48	??0	??ND	??0	??0	??0	??27.91	??0
??ZX-4-16	??16.67	??ND	??14.29	??0	??27.59	??0	??ND	??28.57	??0	??0	??32.56	??5.26
													??ZX-4-17	??16.67	??ND	??35.71	??0	??24.14	??0	??ND	??14.29	??14.29	??4.76	??39.53	??0
??ZX-5-1	??0	??ND	??14.29	??11.11	??17.24	??10.64	??ND	??14.29	??6.12	??28.57	??39.53	??21.05
													??ZX-5-2	??0	??ND	??1429	??5.56	??31.03	??44.68	??ND	??14.29	??0	??23.81	??41.86	??5.26

Compound	??CB	??FO	??CA	??AS	??GZ	??PP	??BC	??PO	??PS	??CL	??RS	??PI
													??ZX-5-3	??0	??ND	??14.29	??0	??10.34	??14.89	??ND	??14.29	??0	??19.05	??18.60	??0.00
??ZX-5-4	??0	??ND	??14.29	??11.11	??20.69	??31.91	??ND	??14.29	??0	??23.81	??48.84	??5.26
													??ZX-5-5	??0	??ND	??14.29	??0	??10.34	??31.91	??ND	??0	??2.04	??19.05	??16.28	??5.26
??ZX-5-6	??0	??ND	??14.29	??16.67	??20.69	??10.64	??ND	??14.29	??0	??19.05	??34.88	??10.53
													??ZX-5-7	??0	??ND	??7.14	??0	??17.24	??40.43	??ND	??0	??0	??33.33	??27.91	??15.79
??ZX-5-8	??16.67	??ND	??21.43	??22.22	??10.34	??23.40	??ND	??0	??0	??23.81	??16.28	??15.79
													??ZX-5-9	??0	??ND	??35.71	??27.78	??44.83	??44.68	??ND	??28.57	??16.33	??28.57	??55.81	??21.05
??ZX-5-10	??0	??ND	??21.43	??11.11	??6.90	??14.89	??ND	??14.29	??0	??19.05	??39.53	??10.53
													??ZX-5-11	??0	??ND	??21.43	??22.22	??20.69	??27.66	??ND	??0	??0	??42.86	??48.84	??21.05
??ZX-5-12	??0	??ND	??14.29	??16.67	??24.14	??19.15	??ND	??0	??0	??19.05	??23.26	??21.05
													??ZX-5-13	??0	??ND	??14.29	??16.67	??27.59	??48.94	??ND	??0	??0	??14.29	??39.53	??10.53
??ZX-5-14	??0	??ND	??14.29	??22.22	??34.48	??31.91	??ND	??0	??0	??33.33	??41.86	??15.79
													??ZX-5-15	??0	??ND	??14.29	??11.11	??17.24	??36.17	??ND	??14.29	??0	??19.05	??46.51	??10.53

Compound	??CB	??FO	??CA	??AS	??GZ	??PP	??BC	??PO	??PS	??CL	??RS	??PI
													??ZX-5-16	??0	??ND	??14.29	??22.22	??24.14	??27.66	??ND	??14.29	??0	??23.81	??32.56	??15.79
??ZX-5-17	??0	??ND	??21.43	??0	??24.14	??27.66	??ND	??14.29	??0	??23.81	??25.58	??15.79
													??ZX-5-18	??0	??ND	??21.43	??22.22	??34.48	??23.40	??ND	??28.57	??0	??14.29	??60.47	??5.26
??TDL	??25.00	??ND	??36.36	??56.25	??9.09	??0	??ND	??14.29	??39.13	??50	??86.96	??18.75
													??ZX-U-17	??0	??ND	??50.00	??16.67	??0	??0	??ND	??14.29	??0	??9.09	??16.28	??5.26
??ZX-U-22	??0	??ND	??11.11	??22.22	??0	??0	??ND	??14.29	??0	??11.11	??18.60	??10.53

ND: undetermined

Contain 4-methyl isophthalic acid, 2, the activity of 3-thiadiazoles derivative resisting tobacco mosaic virus (the withered spot method of half leaf) among table 3 the present invention

ND: undetermined

Part 4-methyl isophthalic acid among table 4 the present invention, 2, the activity and the induced activity of the direct resisting tobacco mosaic virus of 3-thiadiazoles derivative

Table 54-methyl isophthalic acid, 2, the 3-thiadiazoles derivative mixes the working method of using preparation with conventional pesticide

Claims (7)

1.4-methyl isophthalic acid, 2, the 3-thiadiazoles derivative is characterized in that: the chemical structure with following general formula I:

Wherein: R ₁For phenyl or be substituted that base is single to be replaced or disubstituted phenyl, described substituting group for be selected from methyl and (or) group of halogen; R ₂For be selected from phenyl, Chloro-O-Phenyl, a chloro-phenyl-, rubigan, adjacent fluorophenyl, a fluorophenyl, to the group of fluorophenyl, o-trifluoromethyl phenyl, m-trifluoromethylphenyl, p-trifluoromethyl phenyl, ortho-nitrophenyl base, m-nitro base, p-nitrophenyl, o-methyl-phenyl-, an aminomethyl phenyl, p-methylphenyl, p-hydroxybenzene; R ₃For being selected from the group of cyclohexyl or sec.-propyl.

2. the synthetic method of the described Compound I of claim 1 is characterized in that total synthetic route is:

Wherein: R ₁For phenyl or be substituted that base is single to be replaced or disubstituted phenyl, described substituting group for be selected from methyl and (or) group of halogen; R ₂For be selected from phenyl, Chloro-O-Phenyl, a chloro-phenyl-, rubigan, adjacent fluorophenyl, a fluorophenyl, to the group of fluorophenyl, o-trifluoromethyl phenyl, m-trifluoromethylphenyl, p-trifluoromethyl phenyl, ortho-nitrophenyl base, m-nitro base, p-nitrophenyl, o-methyl-phenyl-, an aminomethyl phenyl, p-methylphenyl, p-hydroxybenzene; R ₃For being selected from the group of cyclohexyl or sec.-propyl;

The synthesis step that Compound I is concrete is as follows:

In 50 milliliters of round-bottomed flasks, add 10mL methyl alcohol, the Compound I I that adds own synthetic or purchase then, each 3 mmole of aminated compounds III and aldehyde compound IV and isonitrile compounds V, with reaction system stirring reaction 5 hours at room temperature, after reaction finishes, the decompression desolventizing, solid washs with saturated sodium carbonate after washing with dilute hydrochloric acid again, (eluent is the sherwood oil of 60～90 degree: ethyl acetate) to use 200～300 order silica gel column chromatographies at last, difference according to product, volume ratio is between 8: 1～1: 8, according to the pure product I of gained, calculated yield is measured fusing point, carry out MS and ¹The mensuration of H NMR, the consumption of synthetic compound enlarges according to corresponding proportion or dwindles.

3. the described Compound I of claim 1 is as the purposes of agricultural plants and gardening plant sterilant or antiviral agent.

4. sterilant or antiviral agent is characterized in that: contain Compound I as claimed in claim 1 in the said composition and agricultural goes up acceptable assistant or synergistic agent.

5. the described Compound I of claim 1 is used for the application of inducing plant generation to the pathogen resistance at preparation plant activator.

6. the described Compound I of claim 1 and one or more are selected from down the antiviral agent of group: BTH, TDL, 4-methyl isophthalic acid, 2, the application that 3-thiadiazoles-5-formic acid, DL-beta-aminobutyric acid, virazole, Ningnanmycin, antofine, viral star and XY-13, XY-30 and tisocromide, N-(5-methyl-1,3-thiazole-2-yl)-4-methyl-1,2,3-thiadiazole and Whitfield's ointment combination are used to prepare control viral diseases of plants medicament.

7. fungicidal composition is characterized in that: contain Compound I as claimed in claim 1 in the said composition and one or more are selected from down the sterilant of group: white urea cyanogen, thiram, ziram, zinc manganese ethylenebisdithiocarbamate, phosethyl Al, thiophanate_methyl, m-tetrachlorophthalodinitrile, the enemy can be loose, derosal, procymidone, RP-26019, Vancide 89, the mould prestige of second, ester bacterium urea, fultolanil, F-1991, cyproconazole, methasulfocarb, fenpropidin, dislike acid amides, triazolone, thiophanate methyl, metaxanin, Metalaxyl-M, M 9834, hymexazol, dimethomorph, flumorph, tridemorph, fluzilazol, alkene azoles alcohol, tebuconazole, dislike mould spirit, Difenoconazole, mepanipyrim, Azoxystrobin, Wocosin 50TK, diazosulfide, Whitfield's ointment, tiadinil, tisocromide, N-(5-methyl-1,3-thiazole-2-yl)-4-methyl-1,2,3-thiadiazole and agricultural go up acceptable assistant; Said composition is used for the control to agricultural plants disease and gardening plant disease, and the ratio of wherein said Compound I in composition is 1-90 weight %; The formulation of processing comprises wettable powder, sustained release dosage, pulvis, micro-capsule suspension, can disperse dense dose, seed treatment emulsion, aqueous emulsion, big granula, granule, microemulsion, oil-suspending agent, finish, with seed, suspension concentrates, suspended emulsion agent, water-soluble granule, soluble thick agent, the water-dispersible granules of coated pesticidal.