CN102603670A - 4-(4-methyl-1,2,3-thiadiazole-5-base)-3-alkene-2-ketone ramifications, and preparation method and application thereof - Google Patents

Abstract

The invention provides 4-(4-methyl-1,2,3-thiadiazole-5-base)-3-alkene-2-ketone ramifications, and a preparation method and an application thereof, and relates to heterocyclic compounds which contain 1,2,3-thiadiazole, and the compounds have a chemical structure general formula showed as V. The invention discloses the structure general formula of the compounds, a synthetic method of the compounds, and an application of the compounds when the compounds are used as a bacteriacide. The invention discloses a processing process that the compounds can be mixed with agriculturally acceptable auxiliaries or synergists so as to be used for preparing the bacteriacide, a plant viruses resisting agent and a plant activator; and the invention further discloses the application and the preparation method when the compounds are combined with a commercial insecticide, the bacteriacide, the plant viruses resisting agent and the plant activator for use on disease damage, insect damage and plant virusal diseases in agriculture, forestry and gardening.

Description

One type of 4-(4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-3-alkene-2-ketone derivatives

Technical field

Technical scheme of the present invention relates to and contains the 1,2-diazole compound, is specifically related to 4-(4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-3-alkene-2-ketone derivatives.

Background technology

Alpha, beta-unsaturated ketone is a kind of midbody of important organic synthesis, and it has the conjugated structure of carbonyl and carbon-carbon double bond; Had concurrently ketone compounds and olefin(e) compound reaction property (Zhang Xufei, etc. Zhejiang chemical industry .2008,39 (3): 15-20); Can be used as the Michael addition reaction acceptor compound (Ou Yangyan, etc. the journal .2006 of the Northeast China Normal University, 38 (1): 67-71); Can participate in Diels-Alder reaction (Pei Wen, etc. the journal .1997 of Yanbian University, 23 (3): 37-40) with Baylis-Hillman reaction (Chandrasekhar; S., wait .Tetrahedron Letters.2004,45 (30): 5865-5867); Except the two keys of its carbon-carbon double bond and carbon oxygen also can carry out reduction reaction, the polyreaction, carbon-carbon double bond also can carry out oxidizing reaction.Alpha, beta-unsaturated ketone of a great variety used very extensively; All be widely used at medicine, agricultural and industrial circle, have in the active compound α multiple; Alpha, beta-unsaturated ketone is regarded as important pharmacophoric group, is the important molecule building block of active compound.For example in the medicine, that the compound that contains the alpha, beta-unsaturated ketone group has is antitumor, (Laliberte, R. wait .Canadian J.Pharmaceutical Sci.1967,2 (2): 37-43) for malaria and anti-inflammatory action.As the acceptor of Michael reaction, it is inhibited to the target activity to react with the sulfydryl in target proteins or the target structure.Contain the alpha, beta-unsaturated ketone group verivate-Ethacrynic Acid (Ethacrynic acid, EA); Not only have diuretic properties, or the suppressor factor of GSTPI-1, to killing chemical sproof tumour cell significant activity is arranged; Its mechanism of action is that alpha, beta-unsaturated ketone group and the sulfydryl on the gsh among the EA produced the Michael addition, has suppressed the activity (Li Hongcai of GSTPI-1; Deng. chemical reagent .2009,31 (11): 933-935).Acrylophenone can be used for the synthetic (Wei Wende of sterilant; Deng. Organic Chemicals complete works of (middle volume). the .1999 of Chemical Industry Press); α; Alpha, beta-unsaturated ketone be spices such as oxo α-Zi Luolantong, oxo-alpha, beta-lonone, oxo Beta-methyl jononeionone, verbenone and oxo dorinone synthetic raw material (Sun Baoguo, etc. flavor chemistry and technology. the .2004 of Chemical Industry Press).

α; The preparation method of alpha, beta-unsaturated ketone is quite abundant; Topmost method be through aldol reaction synthesize (Cheng Zhiming, etc. organic synthesis one aldehyde, ketone, quinone. the .1997. of Shanghai science tech publishing house), this method can be through research (the Susumu Saito that selects to avoid the generation of side reaction to improve productive rate and carry out asymmetric synthesis with the method for synthesizing efficient catalyzer; Deng .Angewandte Chemie International Edition.1999,38 (12): 1769-1771; Susumu Saito waits .Chemistry-A European Journal.1999,5 (7): 1959-19621).The method of the synthetic alpha, beta-unsaturated ketone of the present invention is used aldol reaction.Aldol reaction can increase carbochain, and intermolecular aldol condensation can relate to a series of side reaction, causes reaction preference to reduce, and the suitable selection of catalyzer has been played very crucial effect to the selectivity and the product of reaction.An acidic catalyst commonly used in the aldol condensation comprises niobic acid, MFI zeolite, phosphoric acid barium oxide etc.; Basic catalyst has highly basic that weak base is also arranged; (the Tan Lulu such as oxyhydroxide, oxide compound, carbonate, supercarbonate and carboxylate salt etc., organic amine and anionite-exchange resin that comprise basic metal and earth alkali metal; Deng. chemical industry and engineering .2006,23 (1): 70-74).Because the development of organic molecule asymmetry catalysis; In the Application of Catalyst of aldol reaction, obtained widespread use, catalyst for reaction comprises proline(Pro) and verivate (for example L-proline(Pro), proline(Pro) and beta-alkamine synthetic acid amides etc.) thereof, chiral diamine-protonic acid, chirality secondary amine amino acid in nonaqueous phase; Comprise in the aqueous phase catalyst for reaction: tetramethyleneimine-tetrazolium, little peptide molecule, tetramethyleneimine-imidazoles and some alkaloidal metabolites; Metabolite like nicotine mainly is owing to the structure with proline(Pro) has certain similarity (Jiang Lijuan; Deng. organic chemistry .2006,26 (5): 618-626).Use ion liquid method to carry out aldol condensation, mild condition, side reaction few (Loh. waits .Tetrahedron Lett.2002,43,8741).Aldol reaction increases carbochain owing to can form C-C effectively, and its product is applied in industry, medicine and the agricultural widely.

1,2, the 3-thiadiazole compound has wide biological activity equally, and relevant patent and document are summed up and seen Bakulev, et al.Newyork:John Wiley & Sons; Inc, 2004 monograph, the research of relevant thiadiazoles mainly concentrates on 1,3; 4-thiadiazoles derivative, 1,2,5-thiadiazoles derivative and 1,2; On the 4-thiadiazoles derivative, and for 1,2, the active research report of 3-thiadiazoles derivative is but less relatively.1,2,3-thiadiazoles derivative commercial kind in medicine and agricultural chemicals is few, and agriculture field is used has only cotton defoliant--the clever (N-phenyl-N '-1 of disleave; 2,3-thiadiazoles-5-urea, TDZ), plant activator--Acibenzolar (phendioxin, 2; 3-thiadiazoles-7-thiocarboxylic acid methyl esters, BTH), rice field sterilant--tiadinil (3 '-chloro-4,4 '-dimethyl--1; 2,3-thiadiazoles-5-formylaniline, TDL).Contriver's research and design in earlier stage is synthetic and found that the first thiophene lures the inducing anti-disease activity of amine, at present just in the industrialization development process.

In order to seek 1,2 of high biological activity more, 3-thiadiazole new compound, the present invention utilizes the Adol reaction; With 1,2,3-thiadiazoles ring is incorporated into α, in the β beta-unsaturated carbonyl compounds molecule; Design has been synthesized one type and has been contained methyl isophthalic acid, and 2, the α of 3-thiadiazoles; The β beta-unsaturated carbonyl compounds, and carried out the bioactive screening of system, in the hope of the candidate compound being provided for novel pesticide initiative research.

Summary of the invention

Technical problem to be solved by this invention is: new 4-(4-methyl isophthalic acid is provided; 2; 3-thiadiazoles-5-yl)-compound method of 3-alkene-2-ketone derivatives; Provide this compounds to suppress the biological activity and the measuring method thereof of agricultural and gardening and forestry plant pathogen, the middle application of these compounds in agriculture field and gardening field and field of forestry is provided simultaneously.

The present invention solves this technical problem the technical scheme that is adopted: 4-(the 4-methyl isophthalic acid with agriculture field, gardening field, field of forestry insecticidal activity, fungicidal activity, anti-phytoviral activity, inducing plant generation anti-disease activity; 2,3-thiadiazoles-5-yl)-chemical structure of general formula of 3-alkene-2-ketone derivatives sees formula V:

R wherein ₁For being selected from the group of phenyl, 4-nitrophenyl, 4-p-methoxy-phenyl, 4-chloro-phenyl-, 2,4 dichloro benzene base, R ₂For being selected from the group of hydrogen, ethyl, propyl group.

The compound method of 4-of the present invention (4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-3-alkene-2-ketone derivatives V is following:

Wherein: R ₁For being selected from the group of phenyl, 4-nitrophenyl, 4-p-methoxy-phenyl, 4-chloro-phenyl-, 2,4 dichloro benzene base, R ₂For being selected from the group of hydrogen, ethyl, propyl group; R.t.: room temperature; Aq: the aqueous solution; PCC: pyridinium chloro-chromate; NaBH ₄: Peng Qinghuana; EtOH: ethanol; CH ₃OH: ethanol; CH ₂Cl ₂: methylene dichloride;

Specifically be divided into following steps:

A. midbody 4-methyl isophthalic acid, 2, the preparation of 3-thiadiazoles-5-ethyl formate I:

Midbody 4-methyl isophthalic acid, 2,3-thiadiazoles-5-ethyl formate utilizes Hurd-Mori method reference literature (Fan Zhijin, Shi Zugui; Liu Xiufeng, Fan Zhiyin, Ai Yingwei, [1; 2,3] thiadiazoles derivative and preparation method and use thereof, the China national patent of invention is accepted the date: on February 20th, 2006; Application number: 200610013185.5, publication number: CN1810808A, open date: on August 2nd, 2006; The Granted publication date: on September 24th, 2008, the patent No.: ZL 200610013185.5, Granted publication number: method CN 100420686C) is synthetic.

B.4-methyl isophthalic acid, 2, the preparation of 3-thiadiazoles-5-methyl alcohol II:

In 500 milliliters of round-bottomed flasks, add 30 gram 4-methyl isophthalic acids, 2,3-thiadiazoles-5-ethyl formate I; 240 milliliters ethanol under the ice bath agitation condition, adds 13.2 gram Peng Qinghuanas in batches, adds continued and under ice bath, stirs 1 hour; Remove the ice bath stirred overnight at room temperature, after monitoring reaction is accomplished, suction filtration, concentrating under reduced pressure removes and desolvates; Use ethyl acetate extraction, use anhydrous sodium sulfate drying, suction filtration is removed SODIUM SULPHATE ANHYDROUS 99PCT; Concentrating under reduced pressure removes and desolvates, and use the volume ratio sherwood oil: ETHYLE ACETATE is the column chromatography separating purification compound I I of 2: 1 eluents, obtains weak yellow liquid 17.50 grams, and yield is 77%; The 4-methyl isophthalic acid, 2, the amount of 3-thiadiazoles-5-methyl alcohol II preparation enlarges by corresponding proportion or dwindles, and the volume of reaction vessel enlarges by corresponding proportion or dwindles, and commercially available compound I has same effect.

C.4-methyl isophthalic acid, 2, the preparation of 3-thiadiazoles-5-formaldehyde III

In 500 milliliters of round-bottomed flasks, add 10 gram 4-methyl isophthalic acids, 2,3-thiadiazoles-5-methyl alcohol II; 300 milliliters of methylene dichloride add 26.48 gram pyridinium chloro-chromates, stirred overnight at room temperature in batches; After monitoring reaction is accomplished, suction filtration, concentrating under reduced pressure removes and desolvates; Use the volume ratio sherwood oil: ETHYLE ACETATE be 8: 1 eluents through the column chromatography separating purification intermediate III, obtain pale brown look liquid 6.40 grams, yield is 65%.The 4-methyl isophthalic acid, 2, the amount of 3-thiadiazoles-5-formaldehyde III preparation enlarges by corresponding proportion or dwindles, and the volume of reaction vessel enlarges by corresponding proportion or dwindles, and commercially available compound I I has same effect.

D.4-the preparation of (4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-3-alkene-2-ketone V

The preparation of 4-(4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-3-alkene-2-ketone V utilizes the aldol reaction preparation.

In 50 milliliters of round-bottomed flasks, be that 1: 1 ratio adds 4-methyl isophthalic acid, 2,3-thiadiazoles-5-formaldehyde III and ketone compounds IV with mol ratio; Dropwise splash into 0.2 milliliter of 20% sodium hydroxide solution again, stirring at room 3 hours is after monitoring reaction is accomplished; Sodium hydroxide with adding in the adding dilute hydrochloric acid solution is 7 to pH, and concentrating under reduced pressure removes and desolvates, and use the volume ratio sherwood oil: ETHYLE ACETATE is the column chromatography separating purification product V of 8: 1 eluent; Obtain solid, with the pure article calculated yield of gained, different according to the ketone of institute's reaction raw materials; Yield scope from 40% to 60%, measure fusing point with ¹H NMR, the amount of product V enlarges by corresponding proportion or dwindles, and the volume of reaction vessel enlarges by corresponding proportion or dwindles, and commercially available compound III has same effect; Chemical structure and the physico-chemical property of product V are seen table 1.

E.4-the mensuration of (4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-3-alkene-2-ketone V to the pathogenic fungi growth activity:

4-of the present invention (4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-3-alkene-2-ketone V sterilization or bacteriostatic activity adopt thalli growth rate assay method; Detailed process is: get 5 milligrams of sample dissolution in an amount of N, with containing the medicament that a certain amount of polysorbas20 emulsifier aqueous solution is diluted to 500 mcg/ml, will supply the reagent agent under aseptic condition, respectively to draw in 1 milliliter of injection petridish then; Add 9 milliliters of substratum more respectively, it is dull and stereotyped to process 50 mcg/ml pastilles after shaking up, and does 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, be equilateral triangle and put, every processing repetition 3 times; Petridish is placed on cultivation in 24 ± 1 degrees centigrade of constant incubators; Colony diameter to be contrasted expands to 2-3 centimetre of " Invest, Then Investigate " and respectively handles bacterium dish expansion diameter, averages, and relatively calculates relative bacteriostasis rate with blank; Supply the examination bacterial classification to comprise frequently seen plants pathogenic bacteria on the various agricultural, its title and code name comprise AS: tomato early blight bacterium (Alternaria solani); BC: botrytis cinerea pers (Botrytis cinerea); CA: peanut Cercospora bacteria (Cercospora arachidicola); GZ: fusarium graminearum (Gibberella zeae); PI: phytophthora infestans (Phytophthora infestans (Mont.) de Bary); PP: ring rot of apple bacterium (Physalospora piricola); PS: Rhizoctonia solani Kuhn (Pellicularia sasakii); RC: cereal rhizoctonia (Rhizoctonia cerealis); SS: Sclerotinia sclerotiorum (Sclerotinia sclerotiorum), these pathogenic fungies can be represented the kind of most of pathogenic bacteria of the actual generation in field in China's agriculture prodn.

The invention has the beneficial effects as follows: the present invention is to 4-(4-methyl isophthalic acid; 2; 3-thiadiazoles-5-yl)-3-alkene-2-ketone derivatives V carried out the optimization of first guide structure; And the synthetic new compound carried out the screening of bacteriostatic activity and mix to have used research, this compounds can be used to prevent and treat the control of the plant pest in agriculture field and field of forestry and gardening field.

The present invention more specifically explains 4-(4-methyl isophthalic acid through specific preparation and biological activity determination embodiment; 2; 3-thiadiazoles-5-yl)-and synthetic and biological activity and the application thereof of 3-alkene-2-ketone derivatives V, said embodiment only is used for bright specifically the present invention and unrestricted the present invention, especially its biological activity only illustrate; And unrestricted this patent, embodiment is following:

Embodiment 1

The 4-methyl isophthalic acid, 2, the preparation of 3-thiadiazoles-5-methyl alcohol II

In 500 milliliters of round-bottomed flasks, add 30 gram 4-methyl isophthalic acids, 2,3-thiadiazoles-5-ethyl formate; 240 milliliters ethanol under the ice bath agitation condition, adds 13.2 gram Peng Qinghuanas in batches, adds continued and under ice bath, stirs 1 hour; Remove the ice bath stirred overnight at room temperature, after monitoring reaction was accomplished, the suction filtration concentrating under reduced pressure removed and desolvates, and uses ethyl acetate extraction; Use anhydrous sodium sulfate drying, suction filtration is removed SODIUM SULPHATE ANHYDROUS 99PCT, and the suction filtration concentrating under reduced pressure removes and desolvates; Use the volume ratio sherwood oil: ETHYLE ACETATE is the column chromatography separating purification compound of 2: 1 eluents, obtains weak yellow liquid 17.50 grams, and yield is 77%.

Embodiment 2

The 4-methyl isophthalic acid, 2, the preparation of 3-thiadiazoles-5-formaldehyde III

In 500 milliliters of round-bottomed flasks, add 10 gram 4-methyl isophthalic acids, 2,3-thiadiazoles-5-methyl alcohol; 300 milliliters of methylene dichloride add 26.48 gram pyridinium chloro-chromates, stirred overnight at room temperature in batches; After monitoring reaction is accomplished, suction filtration, concentrating under reduced pressure removes and desolvates; Use the volume ratio sherwood oil: ETHYLE ACETATE is the column chromatography separating purification compound of 8: 1 eluents, obtains pale brown look liquid 6.40 grams, and yield is 65%.

Embodiment 3

Synthetic and the structure of compound GDD-II-1:1-(phenyl)-3-(4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl) acrylketone is identified

In 50 milliliters of round-bottomed flasks, be that 1: 1 ratio adds 4-methyl isophthalic acid, 2 with mol ratio; 3-thiadiazoles-5-formaldehyde 0.5 gram and methyl phenyl ketone 0.47 gram, 20 ml methanol dropwise splash into 0.2 milliliter of 20% sodium hydroxide solution catalytic amount again; Stirring at room 3 hours after monitoring reaction is accomplished, adds in the dilute hydrochloric acid solution and the sodium hydroxide that adds; To pH be 7, concentrating under reduced pressure removes and to desolvate, use the volume ratio sherwood oil: ETHYLE ACETATE is the column chromatography separating purification compound of 8: 1 eluent; Obtain yellow solid 0.42 gram, fusing point: 71-73 degree centigrade, yield 47%.Nuclear magnetic data (CDCl ₃, chemical shift): 2.873 (s, 3H, CH ₃), 7.490 (d, J=15.6Hz, 1H, CH), 7.564 (t, J=7.2Hz, 7.6Hz, 2H, ph-H), 7.665 (t, J=7.2Hz, 1H, ph-H), 7.892 (d, J=15.6Hz, 1H, CH), 8.040 (d, J=8.0Hz, 2H, ph-H).

Embodiment 4

Synthetic and the structure of compound GDD-II-2:1-(4-nitrophenyl)-3-(4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl) acrylketone is identified

In 50 milliliters of round-bottomed flasks, be that 1: 1 ratio adds 4-methyl isophthalic acid, 2 with mol ratio; 3-thiadiazoles-5-formaldehyde 0.5 gram and 4-nitro-acetophenone 0.64 gram, 20 ml methanol dropwise splash into 0.2 milliliter of 20% sodium hydroxide solution again; Stirring at room 3 hours after monitoring reaction is accomplished, adds in the dilute hydrochloric acid solution and the sodium hydroxide that adds; To pH be 7, concentrating under reduced pressure removes and to desolvate, use the volume ratio sherwood oil: ETHYLE ACETATE is the column chromatography separating purification compound of 8: 1 eluent; Obtain yellow solid 0.43 gram, fusing point: 85-87 degree centigrade yield 40%.Nuclear magnetic data (CDCl ₃, chemical shift): 2.892 (s, 3H, CH ₃), 7.448 (d, J=15.6Hz, 1H, CH), 7.956 (d, J=15.2Hz, 1H, CH), 8.191 (d, J=8.8Hz, 2H, ph-H), 8.408 (d, J=8.8Hz, 2H, ph-H).

Embodiment 5

Synthetic and the structure of compound GDD-II-3:1-(4-chloro-phenyl-)-3-(4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl) acrylketone is identified

In 50 milliliters of round-bottomed flasks, be that 1: 1 ratio adds 4-methyl isophthalic acid, 2 with mol ratio; 3-thiadiazoles-5-formaldehyde 0.5 gram and 4-chloro-acetophenone 0.60 gram, 20 ml methanol dropwise splash into 0.2 milliliter of 20% sodium hydroxide solution again; Stirring at room 3 hours after monitoring reaction is accomplished, adds in the dilute hydrochloric acid solution and the sodium hydroxide that adds; To pH be 7, concentrating under reduced pressure removes and to desolvate, use the volume ratio sherwood oil: ETHYLE ACETATE is the column chromatography separating purification compound of 8: 1 eluent; Obtain yellow solid 0.53 gram, fusing point: 173-175 degree centigrade, yield 51%.Nuclear magnetic data (CDCl ₃, chemical shift): 2.871 (s, 3H, CH ₃), 7.434 (d, J=7.9Hz, 1H, CH), 7.534 (d, J=8.4Hz, 2H, ph-H), 7.896 (d, J=15.2Hz, 1H, CH), 7.984 (d, J=8.4Hz, 2H, ph-H).

Embodiment 6

Synthetic and the structure of compound GDD-II-4:1-(2,4 dichloro benzene base)-2-ethyl-3-(4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl) acrylketone is identified

In 50 milliliters of round-bottomed flasks, be that 1: 1 ratio adds the 4-methyl isophthalic acid with mol ratio, 2,3-thiadiazoles-5-formaldehyde 0.5 gram and 2; 4-dichlorophenyl propyl ketone 0.85 digests compound, and 20 ml methanol dropwise splash into 0.2 milliliter of 20% sodium hydroxide solution again; Stirring at room 3 hours after monitoring reaction is accomplished, adds in the dilute hydrochloric acid solution and the sodium hydroxide that adds; To pH be 7, concentrating under reduced pressure removes and to desolvate, use the volume ratio sherwood oil: ETHYLE ACETATE is the column chromatography separating purification compound of 8: 1 eluent; Obtain yellow solid 0.50 gram, fusing point: 73-75 degree centigrade, yield 43%.Nuclear magnetic data (CDCl ₃, chemical shift): 1.086 (t, J=7.2Hz, 7.6Hz, 3H, CH ₃), 2.681 (s, 3H, CH ₃), 2.656-2.696 (m, 2H, CH ₂), 7.100 (s, 1H, ph-H), 7.319 (d, J=8.0Hz, 1H, ph-H), 7.392-7.415 (m, 1H, ph-H) 7.510 (d, J=1.6Hz, 1H, CH).

Embodiment 7

Synthetic and the structure of compound GDD-II-5:1-(2,4 dichloro benzene base)-2-propyl group-3-(4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl) acrylketone is identified

In 50 milliliters of round-bottomed flasks, be that 1: 1 ratio adds the 4-methyl isophthalic acid with mol ratio, 2,3-thiadiazoles-5-formaldehyde 0.5 gram and 2; 4-dichlorophenyl butyl ketone 0.9 digests compound, and 20 ml methanol dropwise splash into 0.2 milliliter of 20% sodium hydroxide solution again; Stirring at room 3 hours after monitoring reaction is accomplished, adds in the dilute hydrochloric acid solution and the sodium hydroxide that adds; To pH be 7, concentrating under reduced pressure removes and to desolvate, use the volume ratio sherwood oil: ETHYLE ACETATE is the column chromatography separating purification compound of 8: 1 eluent; Obtain yellow solid 0.71 gram, fusing point: 73-75 degree centigrade, yield 60%; Nuclear magnetic data (CDCl ₃, chemical shift): 1.077 (t, J=7.2Hz, 7.6Hz, 3H, CH ₃), 1.530-1.588 (m, 2H, CH ₂), 2.608 (s, 3H, CH ₃), 2.646-2.686 (m, 2H, CH ₂), 7.087 (s, 1H, ph-H), 7.306 (d, J=8.0Hz, 1H, ph-H), 7.394 (dd, J=8.4Hz, 2.0Hz, 1H, ph-H), 7.501 (d, J=1.6Hz, 1H, CH).

Embodiment 8

Antibacterial or the fungicidal activity of 4-of the present invention (4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-3-alkene-2-ketone V:

The title and the code name of the frequently seen plants pathogenic fungi of the present invention's test comprise AS: tomato early blight bacterium (Alternaria solani); BC: botrytis cinerea pers (Botrytis cinerea); CA: peanut Cercospora bacteria (Cercospora arachidicola); GZ: fusarium graminearum (Gibberella zeae); PI: phytophthora infestans (Phytophthora infestans (Mont.) de Bary); PP: ring rot of apple bacterium (Physalospora piricola); PS: Rhizoctonia solani Kuhn (Pellicularia sasakii); RC: cereal rhizoctonia (Rhizoctonia cerealis); SS: Sclerotinia sclerotiorum (Sclerotinia sclerotiorum), these bacterial classifications have good representativeness, can represent the kind of most of pathogenic bacteria that the field takes place in the agriculture prodn.Thalli growth rate method is measured the result and is seen table 2, and table 2 shows that when 50 mcg/ml, all compounds of synthetic of the present invention all have fungicidal activity in various degree, and especially outstanding is synthetic compound GDD-II-1 of the present invention is higher than 70% to the fungicidal activity of GZ; GDD-II-1, GDD-II-4 and GDD-II-5 are higher than 60% to the fungicidal activity of PP; GDD-II-1, GDD-II-3 are higher than 60% to the fungicidal activity of BC; GDD-II-1, GDD-II-2, GDD-II-4, GDD-II-5 are higher than 60% to the fungicidal activity of RC; GDD-II-1, GDD-II-3, GDD-II-4, GDD-II-5 are higher than 60% to the fungicidal activity of PS; Therefore, this compounds has shown fungicidal activity preferably.

Embodiment 9

4-of the present invention (4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-3-alkene-2-ketone derivatives V and antiviral agent are combined in the application in control agricultural and forestry and the gardening plant virus disease

4-(4-methyl isophthalic acid; 2; 3-thiadiazoles-5-yl)-and 3-alkene-2-ketone derivatives V and existing Antiphytoviral medicament diazosulfide, tiadinil (TDL), different metsulfovax (isotianil), 4-methyl isophthalic acid, 2,3-thiadiazoles-5-formic acid, 4-methyl isophthalic acid; 2; 3-thiadiazoles-5-sodium formiate, 4-methyl isophthalic acid, 2,3-thiadiazoles-5-ethyl formate, DL-beta-aminobutyric acid, virazole, antofine, Ningnanmycin, tisocromide, first thiophene lure any 1 or 2 compounds combinations in amine or Whitfield's ointment, cytosintetidemycin, dichloro-isonicotinic acid, allyl isothiazole, well ridge azanol, the jingganmycin; Be used to prevent and treat the agricultural plants virus disease; These virus diseases are selected from tobacco mosaic virus disease, various melon virus disease, various solanberry viroid disease, beans virus disease, Cruciferae virus disease, grain and oil crop virus disease, cotton virus disease and the various fruit tree virus disease any, wherein endanger serious being selected from: tobacco virus, peppery pimento virus disease, tomato virus disease, Chinese cabbage virus disease, paddy rice virus disease comprise in rice dwarf virus disease, BYDV, stripe virus disease, fern leaf of tomato viral disease, chilli pepper mosaic virus disease and tobacco veinal necrosis virus disease, corn short mosaic disease, cauliflower mosaic virus, oranges and tangerines virus disease, cymbidium mosaic virus, the cybidium ring spot virus any.The crop that these compsns are suitable for be selected from paddy, wheat, barley, oat, corn, Chinese sorghum, sweet potato, yam, cassava, soybean, pea-pods, broad bean, pea, mung bean, red bean, cotton, silkworm and mulberry, peanut, rape, sesame, Sunflower Receptacle, beet, sugarcane, coffee, cocoa, genseng, the bulb of fritillary, rubber, coconut, oil palm, sisal hemp, tobacco, tomato, capsicum, radish, cucumber, Chinese cabbage, celery, hot pickled mustard tube, beet, rape, green onion, garlic, watermelon, muskmelon, hami melon, pawpaw, really, tea, wild vegetable, bamboo shoots, hops, yam, paddy rice, pepper, apple, banana, citrus, plants such as agricultural, gardening, economy, forestry such as peach, papaya, orchid, potted landscape; The use of these compsns makes the immunizing power of crop self be improved, and when producing the control of insect especially infection insect, has induced plant to produce the control to viral diseases of plants; Also can produce the direct control effect of virus disease; Therefore, these compsns can be used for Antiphytoviral medicament and inducing plant Antiphytoviral preparation of medicaments and purposes.4-of the present invention (4-methyl isophthalic acid; 2; 3-thiadiazoles-5-yl)-the total quality percentage composition of 3-alkene-2-ketone derivatives V in compsn is 1%-90%; The ratio of 4-of the present invention (4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-3-alkene-2-ketone derivatives V and commercially available agricultural chemical is mass percent 1%: 99% to 99%: 1%; The formulation of compsn processing is selected from wettable powder; Sustained release dosage; Pulvis; Micro-capsule suspension; The dispersible body preparation; The dispersible solid preparation; Seed treatment emulsion; Aqueous emulsion; Big granula; Granule; Microemulsion; Oil-suspending agent; Finish; Seed with coated pesticidal; Suspended emulsion agent; Water-soluble granule; Soluble thick agent; Water-dispersible granules; Poison grain; Aerosol; Block poison bait; Sustained-release block; Dense poison bait; The capsule granula; Capsule suspension; Can disperse dense dose; Pulvis; Dry mixing kind pulvis; Missible oil; The electrostatic spray agent; Water-in-oil emulsion; Seed treatment agent; Oil-in-water emulsion; Smoke candle; Granula subtilis; Smoke candle; Smoke cartridge; The smog rod; The seed treatment suspension agent; The smog sheet; Smoke substance; The smog ball; Granular poison bait; Foaming agent; Big granula; The drift pulvis; Granula; Ointment; Thermal fog; Solid-liquid mixes the dress agent; Liquid/liquid mixes the dress agent; Cold mist agent; Gu Gu/mix and adorn agent; The medicine lacquer; The seed treatment liquor; Microgranules; Oil suspending agent; Finish; The oil-dispersing property pulvis; Paste; The sheet poison bait; Dense jelly; Sprinkle and water agent; Stylus; Plant the clothing agent; Poison bait; Basting agent; The fritter poison bait; Suspension agent; Suspension emulsion; Water-soluble granule; Soluble thick agent; The film forming finish; Soluble powder; The seed treatment water solube powder; The ultra-low volume suspension agent; Tablet; Follow the trail of pulvis; Ultra low volume liquids; The steam releasing agent; Water-dispersible granules; Wettable powder; In the wet-mixing kind water-dispersible powder any one; All show addition or synergism between these compsns, when keeping insecticidal activity, the effect that its antiviral activity all uses separately greater than any one compound; Do not find to have the compsn of antagonistic action, the drug effect lasting period of compsn is long.

Can know 4-(4-methyl isophthalic acid, 2 from the basic principles of chemistry; 3-thiadiazoles-5-yl) thereby-3-alkene-2-ketone derivatives V can produce 4-methyl isophthalic acid, 2,3-thiadiazoles-5-formic acid from carbonyl fracture in plant with after the water molecules effect; Confirm also that through relevant software prediction and test compound of the present invention can produce 4-methyl isophthalic acid, 2,3-thiadiazoles-5-formic acid in the degraded of plant materials intracellular metabolite; Bibliographical information confirms the 4-methyl isophthalic acid; 2,3-thiadiazoles-5-formic acid has inducing plant and produces the resistance to the phytopathy original, can be used in the control of Plant diseases and viral diseases of plants.Therefore, these compsns can be used in preparation Antiphytoviral medicament and inducing plant Antiphytoviral medicament.Compsn has improved the defence capability of plant in Antiphytoviral, make plant produce the defence capability to pathogenic fungi, bacterium and virus infection.

Embodiment 10

Application in 4-of the present invention (4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-3-alkene-2-ketone derivatives V and sterilant combination control agricultural and forestry and the gardening plant insect pest

4-of the present invention (4-methyl isophthalic acid; 2; 3-thiadiazoles-5-yl)-the total quality percentage composition of 3-alkene-2-ketone derivatives V in compsn is 1%-90%; The ratio of 4-of the present invention (4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-3-alkene-2-ketone derivatives V and commercially available agricultural chemical is mass percent 1%: 99% to 99%: 1%; Spray after can directly converting water; Comprise agricultural in its preparation and go up acceptable solvent and emulsifying agent and solubility promoter and synergistic agent etc., Gu the formulation of compsn processing be selected from wettable powder, sustained release dosage, pulvis, micro-capsule suspension, dispersible body preparation, dispersible solid preparation, seed treatment emulsion, aqueous emulsion, big granula, granule, microemulsion, oil-suspending agent, finish, the seed with coated pesticidal, suspended emulsion agent, water-soluble granule, soluble thick agent, water-dispersible granules, poison grain, aerosol, block poison bait, sustained-release block, dense poison bait, capsule granula, capsule suspension, can disperse dense dose, pulvis, dry mixing kind pulvis, missible oil, electrostatic spray agent, water-in-oil emulsion, seed treatment agent, oil-in-water emulsion, smoke candle, granula subtilis, smoke candle, smoke cartridge, smog rod, seed treatment suspension agent, smog sheet, smoke substance, smog ball, granular poison bait, foaming agent, big granula, drift pulvis, granula, ointment, thermal fog, solid-liquid mix dress agent, liquid/liquid mix dress agent, cold mist agent, admittedly/mixing adorns agent, medicine lacquer, seed treatment liquor, microgranules, oil suspending agent, finish, oil-dispersing property pulvis, paste, sheet poison bait, dense jelly, bold and vigorously waters in agent, stylus, the agent of kind clothing, poison bait, basting agent, fritter poison bait, suspension agent, suspension emulsion, water-soluble granule, soluble thick agent, film forming finish, soluble powder, seed treatment water solube powder, ultra-low volume suspension agent, tablet, tracking pulvis, ultra low volume liquids, steam releasing agent, water-dispersible granules, wettable powder, the wet-mixing kind water-dispersible powder any one; The insect pest that can prevent and treat mainly contains red spider, Asiatic migrotory locust, clouding car locust, Chinese rice grasshopper, Patanga japonica (l.Bol.), single thorn mole cricket, east mole cricket, rice thrips, onion thrips, greenhouse thrips, haplothrips aculeatus, Mai Jian pipe thrips, Trialeurodes vaporariorum Westwood, Bemisia tabaci, rice green leafhopper, green leaf hopper, chlorita biguttula, spot clothing plant hopper, brown paddy plant hopper, white backed planthopper, small brown rice planthopper, the flat angle of sugarcane plant hopper, cotten aphid, green bugs, grain aphid, black peach aphid, kaoliang aphid, radish aphid, icerya purchasi, Pseudaulacaspis pentagona, unaspis shield kuwana, san jose scale, wax insect, ceroplastes rubens, the hard a red-spotted lizard of Korea's ball, pear lace bug, banana lace bug, thin corner piece stinkbug, little minute pirate bugs, slender rice bug, paddy fly, niphe elongata, scotinophora lurida, Nezara viridula smaragdula Fabricius., green plant bug, alfalfa plant bug, black striped plant bug, chrysopa septempunctata, beautiful Chrysopa, Chinese green lacewing, rain moth, casemaking clothes moth, cnidocampa flavescens walker, brown slug moth, thosea siensis, gelechiid, pink bollworm, brachmia triannuella, small cabbage moth, small heart-eating peach worm, eating-core bean worm, small heart-eating peach worm, apple Spilonota lechriaspis, brown belt length leaf roller, intends smaller apple leaf roller, striped rice borer, bean-pod borer, Pyrausta nubilalis (Hubern)., yellow rice borer, Oeobia undalis, Cnaphalocrocis medinali(rice leaf roller), bar snout moth's larva, the wild snout moth's larva of lap leaf, dichocrocis punctiferalis, armyworm, prodenia litura, rice green caterpillar, anomis flava, beet armyworm, pink rice borer, bollworm, ancient cooking vessel selects diamond drill, black cutworm, big cutworm, yellow cutworm, robber poison moth, gypsymoth, palaearctic sweet potato, greenish brown hawk moth, straight burr rice hesperiidae, pelopidas mathias, oranges and tangerines swallowtail butterfly, Common Mormon, small white, pyrameis indica, the yellow a kind of butterfly harmful to crop plants of ramie, beans blister beetle, Venus ground beetle, wrinkle sheath ground beetle, wheat head ground beetle, pleonomus canaliculatus, Agriotes subrittatus Motschulsky, khapra beetle, attagenus piceus, the little buprestid beetle of oranges and tangerines, golden edge buprestid beetle, tenebrio molitor, dark mealworm, red flour beetle, confused flour beetle, verdigris different beetle, black dull cockchafer, holotrichia oblita, mulberry borer, longicorn beetle, nadezhdiella cantori, pink neck longicorn, big daikon leaf beetle, daicon leaf beetle, aulacophora femoralis, Phyllotreta striolata, Callosobruchus chinensis, pea weevil, broad bean weevil, sitophilus zea-mais, rice weevil, dolerus tritici, pear fruit sawfly, yellowish leukorrhea ichneumon wasp, armyworm white star ichneumon wasp, the outstanding cocoon ichneumon wasp of corn earworm, bollworm tooth lip ichneumon wasp, snout moth's larva stain wart ichneumon wasp, mosquito, fly, horsefly, wheat midge, contarinia tritici, pachydiplosis oryzae, citrus fruit fly, melon trypetid, wheat leaf ash are dived fly, Americal rice leaf miner, the black fly of diving of beans stalk, frit fly, kind fly, onion fly, radish fly, full skirt chase after and post that fly, Pyrausta nubilalis (Hubern). are strictly posted fly, armyworm lacks Agricultural pests, forestry pest, gardening pest insect and sanitary insect pests such as must posting fly, and the controlling mode while also comprises double controlling; 4-of the present invention (4-methyl isophthalic acid; 2; 3-thiadiazoles-5-yl)-3-alkene-2-ketone derivatives V can with the sterilant of following group in one or more mixes uses: Chlorpyrifos 94, inferior Nong, acetamiprid, Affirm (Merck Co.), more visit that rhzomorph, Avrmectin, pleocidin, fenvalerate, efficient fenvalerate, PP-383, beta_cypermethrin, lambda-cyhalothrin, Deltamethrin, Fenvalerate, Beta-FCR-1272, FCR-1272, Lambda-lambda-cyhalothrin, Permanone, permethrin, esbiothrin, cyhalothrin, bifenthrin, WL 43479, ether chrysanthemum ester, flumethrin, fluvalinate, Provado, acetamiprid, Ti304, imidaclothiz, thiophene worm quinoline, thiophene worm piperazine, thiophene worm amine, MTI-446, clothianadin, Da Tenan, diflubenzuron, the young urea that goes out, Teflubenzuron, deinsectization swell, fluorine bell urea, WL 115110, pyridine worm swell, Acarus tritici urea, poisonous insect urea, penfluron, Noviflumuron are noviflumuron; Its CAS number for 121451-02-3, flucycloxuron, Novaluron be Rimon, fluorine pyridine urea, Bay sir 6874 promptly { 1-[(3.5-two chloro-4) 4-nitrophenoxy phenyl 3-3-(2-chlorobenzene)-urea }, Bay SIR-8514 promptly [1-(4-Trifluoromethoxyphen-l)-3-(2-chlorobenzene)-urea], piperazine worm urea, promptly two three WL 115110s of Bistrifluron, furans worm hydrazides, worm hydrazides, chlorine worm hydrazides, methoxyfenozide, ring worm hydrazides, Rogor, omethoate, SD-1750, acephate, triazophos, Resitox, pyridaphenthione, isazofos, Ro 7-5050, SevinCarbaryl, PP-062, MTMC, isoprocarb, cartap, fenobucarb, leaf disperse, carbaryl, benfuracarb, carbosulfan, cartap, bromopropylate, hexythiazox, azoles mite ester, pyridaben, four mite piperazines, alkynes mite spy, butyl ether urea, benfuracarb, pyrrole aphid ketone, spiral shell mite ester, spiral shell worm ester, spiral shell worm ethyl ester, butene-fipronil, azocyclotin, PP618, ethoprophos, fluorine worm nitrile, desinsection list, disosultap, chlorine insect amide, Flubendiamide, fluorine cyanogen insect amide, cyanogen insect amide, azoles insect amide, tebufenpyrad, bromothalonil, pyrazine ketone, second mite azoles, tebufenpyrad, the young ketone of rattling away, pyrrole propyl ether, emaricin etc.; The control effect of compsn is good, and drug effect is played stably.The crop that these compsns are suitable for comprise paddy, wheat, barley, oat, corn, Chinese sorghum, sweet potato, yam, cassava, soybean, pea-pods, broad bean, pea, mung bean, red bean, cotton, silkworm and mulberry, peanut, rape, sesame, Sunflower Receptacle, beet, sugarcane, coffee, cocoa, genseng, the bulb of fritillary, rubber, coconut, oil palm, sisal hemp, tobacco, tomato, capsicum, radish, cucumber, Chinese cabbage, celery, hot pickled mustard tube, beet, rape, green onion, garlic, watermelon, muskmelon, hami melon, pawpaw, really, tea, wild vegetable, bamboo shoots, hops, yam, paddy rice, pepper, apple, banana, citrus, peach, papaya, orchid, potted landscape.Compsn makes plant produce the defence capability to pathogenic fungi, bacterium and virus infection in the parasiticidal defence capability that improves plant simultaneously.

Embodiment 11

Application in 4-of the present invention (4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-3-alkene-2-ketone derivatives V and sterilant combination control agricultural and forestry and the gardening plant disease

All the present invention is 4 - (4 - methyl-1, 2,3 - thiadiazol-5 - yl) -3 - en-2 - one derivatives V with existing fungicides such as benzothiadiazole, amine acid bacteria thiophene, thiazole amide, amine induced a thiophene 4 - methyl-1, 2,3 - thiadiazole-5 - carboxylic acid 4 - methyl-1, 2,3 - thiadiazole-5 - Sodium 4 - methyl-1, 2,3 - thiadiazole-5 - carboxylic acid ethyl ester, DL-β-aminobutyric acid, Isotianil (isotianil), ribavirin, An Tuofen, or Ningnanmycin salicylic acid, Cymoxanil, thiram, ziram, mancozeb, fosetyl, thiophanate-methyl, chlorothalonil, the enemy can be loose, procymidone, Fenpropidine, thiophanate-methyl, thiophanate, metalaxyl, salicylic acid, flumorph, Dimethomorph, efficient metalaxyl, efficient Benalaxyl, double-cypermethrin bacteria amine, flusulfamide, A flusulfamide, thiophene amine fluoride bacteria , flutolanil, leaf blight phthalate, cyclopropane amino acid bacteria, cyflufenamid, cycloalkyl amine acid bacteria, cyano bacteria amine, amine silica thiabendazole, furosemide topiramate amine bacteria, penthiopyrad, diacetylene amine acid bacteria, benzene amine acid bacteria, ofurace, carboxin, B strains Lee, iprodione, azoxystrobin, Kresoxim amines, fluoxastrobin, kresoxim, phenoxy bacteria amines, amine oxime ether bacteria, aerobic bacteria pyridine esters, pyraclostrobin, trifloxystrobin, enestroburin, allyl amine oxime bacteria, oxygen propiconazole, bromuconazole, cyproconazole, difenoconazole azole, Diniconazole, efficient diniconazole, fluorine Propiconazole, fenbuconazole, fluoro quinazoline, flusilazole, flutriafol, hexaconazole, imines azole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, Prothioconazole azole, simeconazole, tebuconazole, PTFE ether, triazole alcohol, sterilization azole, Bitertanol, thiabendazole, fuberidazole, imazalil, efficient imazalil, prochloraz, triflumizole, Cyazofamid, imidazole cycloheximide, evil imidazole, pefurazoate, Famoxadone, pyridine bacteria oxazole, hymexazol oxadixyl, thiophene pyraclostrobin, earth benomyl, octyl thiophene ketones, benzene thiophene thiocyanate, dodecyl tridemorph, fenpropimorph, tridemorph, fenpiclonil, fludioxonil, fluazinam, piperidine oxime spots, fungus amine piperidine ring, boscalid, fluazinam acid bacteria amines, amine piperidine bacteria, cyprodinil, mepanipyrim fluorine, ferimzone, mepanipyrim, pyrimethanil, fenarimol, nuarimol, Chinomethionate, dithianon, ethoxyquin morpholine, hydroxy quinoline, quinoline propoxyphene, phenoxy quinoline, diethofencarb, isopropyl bacteria amines, benzene thiabendazole amines Propamocarb, sulfur bacteria Granville, edifenphos, iprobenfos, topiramate bacteria phosphorus , methyl Tolclofos, blasticidin, kasugamycin, polymyxin, Polyoxin, validamycin, Jinggangmycin, streptomycin, metalaxyl, furalaxyl, Benalaxyl, furosemide amide, mepronil, carbendazim, benomyl, thiophanate-methyl, triadimefon, ethirimol sulfonate, dimethyl ethyl phenol, ethirimol, captafol, captan, sterilization Dan, vinclozolin, chlorofluorocarbons sclerotia Lee, Dimetachlone, chlorothalonil, Isoprothiolane, kitazine, leaf blight, PCNB, mancozeb, Propineb, triacetate phosphonic acid aluminum, sulfur, Bordeaux mixture, copper sulfate, copper oxychloride, cuprous oxide, cupric hydroxide, benzene cycloheximide, pencycuron, pyridazine cycloheximide tetrachlorophthalide, pyroquilon, spiro amine mellea , Tricyclazole, triforine, more fruit pyridine, Iminoctadine salt Iminoctadine amine, Dicloran, flusulfamide benzene, toluene flusulfamide, indole ester Fenaminosulf, oxolinic acid, allyl benzene thiazole, bronopol, methyl iodide, metam sodium, the enemy lines esters, dazomet, dichloro-isopropyl ether, Fosthiazate, Cadusafos, fensulfothion, insects fenamiphos, fenamiphos, Ethoprophos, except Line phosphorus, chlorine triazophos, carbosulfan cyclophosphamide, oxamyl, aldicarb, carbofuran, sulfuryl fluoride, dichloropropene, dichloro-isonicotinic acid, allyl isothiazolin any other known as sterilization agent in combination with any one or two; the present invention is 4 - (4 - methyl-1, 2,3 - thiadiazol-5 - yl) -3 - en-2 - one derivatives V in combination was in the percentage of the total mass of 1% -90%, the present invention is 4 - (4 - methyl-1, 2,3 - thiadiazol-5 - yl) -3 - en-2 - one derivatives object V with a mass ratio of pesticide products Percentage 1%: 99% to 99%: 1%; pharmaceutical control effect is good, these compositions have a synergistic effect and the additive effect, we have not found to have a composition antagonistic effect ; The composition can be used for agricultural and horticultural plant disease plant disease prevention, control objects include Oomycete the genus Achlya, Aphanomyces spp, Pythium, Phytophthora, referring Terrier spp, Plasmopara genus false downy mildew genus Peronospora spp produced more than twenty genera diseases, such as cotton seedlings rot, root rot of tomato, potato late blight, tobacco black shank, millet powdery mildew, downy mildew of grape, lettuce downy mildew, cucumber downy mildew, cucumber anthracnose and other crops, crops, horticultural and forestry plants, other diseases, etc.; processing composition selected from a wettable powder formulations, release agent, powder, microcapsule suspensions, dispersible liquid formulations, dispersible solid preparation, seed treatment, emulsions, aqueous emulsion, large grain, granules, micro-emulsions, oil suspensions, oil, seed coated with a pesticide, suspension emulsion, water-soluble granules , soluble concentrate agent, water dispersible granules, poison Valley, aerosols, block bait, release block, concentrated bait, capsules granules, capsules suspensions, dispersible concentrate, powder, dry dressing powders, emulsifiable concentrates , electrostatic sprays, oil-in-water emulsion, seed treatment agent, water-in-oil emulsions, aerosol cans, fine granules, smoke candle, smoke cartridges, smoke stick, suspension for seed treatment, smoke tablet, aerosol, smoke pellet, granular bait, gas evolution agents, large granules, drifting powders, granules, ointments, thermal fog, solid / liquid mixing device agent, liquid / liquid mixing device agents, fog agent, solid / solid mixing device agent, drug paint, Seed treatment liquid, particulates, oils suspending agents, oil, oil dispersible powders, creams, flaky baits, thick glue, sprinkling agents, stick agents, seed coating, bait, liniment, small baits, suspensions, emulsions suspensions, water-soluble granule, soluble concentrate agents, film oil, soluble powders, water soluble powder for seed treatment, ultra low volume suspension, tablet, tracking powder, ultra low volume liquid, vapor release agent , water dispersible granules, wettable powders, water dispersible powder wet dressing of any one.The crop that these compsns are suitable for comprise cereal (comprising paddy, wheat, barley, oat, corn, millet, Chinese sorghum etc.), tuber crops (comprising sweet potato, yam, cassava etc.), beans (comprising soybean, broad bean, pea, mung bean, red bean etc.) and fiber (cotton, crudefiber crop, silkworm and mulberry etc.), oil plant (peanut, rape, sesame, soybean, Sunflower Receptacle etc.), sugar material (beet, sugarcane etc.), beverage (tealeaves, coffee, cocoa etc.), hobby (tobacco leaf etc.), medicinal (genseng, the bulb of fritillary etc.), the torrid zone (rubber, coconut, oil palm, the sisal hemp etc.) food crop of etc.ing and fruit, flowers, oil plant, sugared expect and cash crop such as cotton, fiber crops, tea, tobacco, Chinese medicinal materials and plant melon, really, tea, silkworm and mulberry, vegetables (containing various wild vegetable etc.), bamboo shoots, flowers and garden crop such as tobacco (flue-cured tobaccos such as ornamental plant, hops, medicinal material, pepper, seedling and other garden crops; Air-curing of tobacco leaves, suncured tabacco), vegetables, (tomato, capsicum, radish, cucumber, Chinese cabbage, celery, hot pickled mustard tube, beet, rape, green onion, garlic etc.), melon (watermelon, muskmelon, hami melon, pawpaw etc.), beans (soybean, broad bean, pea-pods etc.), yam, wheat, corn, paddy rice, peanut, fruit tree, (apple, banana, citrus, peach, papaya), flowers (like orchid), potted landscape etc.Compsn makes plant produce the defence capability to pathogenic fungi, bacterium and virus infection in the germ-resistant defence capability that improves plant simultaneously.

Embodiment 12

The complete processing and the stability of 4-of the present invention (4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-3-alkene-2-ketone derivatives V and commercially available agricultural chemical compound preparation

4-of the present invention (4-methyl isophthalic acid; 2,3-thiadiazoles-5-yl)-the mixed preparation complete processing of 3-alkene-2-ketone derivatives V and commercially available agricultural chemical sees table 3, and is visible by table 3; Most medicament all can be processed according to the method for statement; The main component of liquid preparation is other a component etc. of effective constituent and solubility promoter and tensio-active agent, synergistic agent, antifreezing agent, stablizer, thickening material or permeate agent etc., and the composition of solid preparation mainly includes imitates other agriculturals such as composition, tensio-active agent and filler and go up acceptable adjuvant components, the cold storage test of process preparation; Liquid preparation is placed 1 week not have to precipitate at 0 ± 2 degree centigrade and is separated out; Solid preparation placed for 2 weeks at 54 ± 2 degrees centigrade, and caking phenomenon does not appear in medicament, and the medicament drug effect that all preparations store before and after placing does not have significant difference; The rate of decomposition of compsn effective constituent in 5%, the composite preparation qualified stability.

Chemical structure and the physical and chemical parameter of table 1 4-of the present invention (4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-3-alkene-2-ketone derivatives V

The fungicidal activity of table 2 synthetic 4-of the present invention (4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-3-alkene-2-ketone derivatives V (/ %)

Compound	AS	CA	GZ	PP	BC	SS	RC	PS	PI
										GDD-II-1	40.00	30.43	74.60	62.90	60.00	30.77	62.00	69.01	37.04
GDD-II-2	20.00	13.04	26.98	51.61	33.33	28.85	60.00	59.15	18.52
										GDD-II-3	36.67	34.78	57.14	59.68	71.67	26.92	18.00	76.06	33.33
GDD-II-4	25.00	40.74	48.98	77.22	50.00	46.15	78.05	73.33	42.31
										GDD-II-5	50.00	37.04	36.73	60.76	46.30	55.77	80.49	68.33	34.62

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

Table 3 4-of the present invention (4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-3-alkene-2-ketone derivatives V and commercially available agricultural chemical are used working method with

Claims (6)

1. one type of 4-(4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-3-alkene-2-ketone derivatives is characterized in that having the chemical structure of general formula suc as formula shown in the V:

Wherein: R ₁For being selected from the group of phenyl, 4-nitrophenyl, 4-p-methoxy-phenyl, 4-chloro-phenyl-, 2,4 dichloro benzene base, R ₂For being selected from the group of hydrogen, ethyl, propyl group.

2. the compound method of the described 4-of claim 1 (4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-3-alkene-2-ketone derivatives V, concrete synthetic route is following:

Wherein: R ₁For being selected from the group of phenyl, 4-nitrophenyl, 4-p-methoxy-phenyl, 4-chloro-phenyl-, 2,4 dichloro benzene base, R ₂For being selected from the group of hydrogen, ethyl, propyl group; R.t.: room temperature; Aq: the aqueous solution; PCC: pyridinium chloro-chromate; NaBH ₄: Peng Qinghuana; EtOH: ethanol; CH ₃OH: ethanol; CH ₂Cl ₂: methylene dichloride;

Specifically be divided into following steps:

A.4-methyl isophthalic acid, 2, the preparation of 3-thiadiazoles-5-methyl alcohol II:

In 500 milliliters of round-bottomed flasks, add 30 gram 4-methyl isophthalic acids, 2,3-thiadiazoles-5-ethyl formate I; 240 milliliters ethanol under the ice bath agitation condition, adds 13.2 gram Peng Qinghuanas in batches, adds continued and under ice bath, stirs 1 hour; Remove the ice bath stirred overnight at room temperature, after monitoring reaction is accomplished, suction filtration, concentrating under reduced pressure removes and desolvates; Use ethyl acetate extraction, use anhydrous sodium sulfate drying, suction filtration is removed SODIUM SULPHATE ANHYDROUS 99PCT; Concentrating under reduced pressure removes and desolvates, and use the volume ratio sherwood oil: ETHYLE ACETATE is the column chromatography separating purification compound I I of 2: 1 eluents, obtains weak yellow liquid 17.50 grams, and yield is 77%; The 4-methyl isophthalic acid, 2, the amount of 3-thiadiazoles-5-methyl alcohol II preparation enlarges by corresponding proportion or dwindles, and the volume of reaction vessel enlarges by corresponding proportion or dwindles, and commercially available compound I has same effect;

B.4-methyl isophthalic acid, 2, the preparation of 3-thiadiazoles-5-formaldehyde III

In 500 milliliters of round-bottomed flasks, add 10 gram 4-methyl isophthalic acids, 2,3-thiadiazoles-5-methyl alcohol II; 300 milliliters of methylene dichloride add 26.48 gram pyridinium chloro-chromates, stirred overnight at room temperature in batches; After monitoring reaction is accomplished, suction filtration, concentrating under reduced pressure removes and desolvates; Use the volume ratio sherwood oil: ETHYLE ACETATE be 8: 1 eluents through the column chromatography separating purification intermediate III, obtain pale brown look liquid 6.40 grams, yield is 65%; The 4-methyl isophthalic acid, 2, the amount of 3-thiadiazoles-5-formaldehyde III preparation enlarges by corresponding proportion or dwindles, and the volume of reaction vessel enlarges by corresponding proportion or dwindles, and commercially available compound I I has same effect;

C.4-the preparation of (4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-3-alkene-2-ketone V

The preparation of 4-(4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-3-alkene-2-ketone V utilizes the aldol reaction preparation:

In 50 milliliters of round-bottomed flasks, be that 1: 1 ratio adds 4-methyl isophthalic acid, 2,3-thiadiazoles-5-formaldehyde III and ketone compounds IV with mol ratio; Dropwise splash into 0.2 milliliter of 20% sodium hydroxide solution again, stirring at room 3 hours is after monitoring reaction is accomplished; Adding in the dilute hydrochloric acid solution with the sodium hydroxide that adds is 7 to pH, and concentrating under reduced pressure removes and desolvates, and uses the volume ratio sherwood oil: ETHYLE ACETATE be the column chromatography of 8: 1 eluent separate the solid product V of purifying; With the pure article calculated yield of gained; Different according to the ketone of institute's reaction raw materials, yield scope from 40% to 60%, measure fusing point with ¹H NMR, the amount of product V enlarges by corresponding proportion or dwindles, and the volume of reaction vessel enlarges by corresponding proportion or dwindles, and commercially available compound III has same effect.

3. the described 4-of claim 1 (4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-3-alkene-2-ketone V goes up the purposes of acceptable assistant in the preparation sterilant with agricultural.

4. the described 4-of claim 1 (4-methyl isophthalic acid; 2; 3-thiadiazoles-5-yl)-3-alkene-2-ketone V and agricultural go up acceptable assistant and be selected from Chlorpyrifos 94, inferior Nong, acetamiprid, Affirm (Merck Co.), more visit that rhzomorph, Avrmectin, pleocidin, fenvalerate, efficient fenvalerate, PP-383, beta_cypermethrin, lambda-cyhalothrin, Deltamethrin, Fenvalerate, Beta-FCR-1272, FCR-1272, Lambda-lambda-cyhalothrin, Permanone, permethrin, esbiothrin, cyhalothrin, bifenthrin, WL 43479, ether chrysanthemum ester, flumethrin, fluvalinate, Provado, acetamiprid, Ti304, imidaclothiz, thiophene worm quinoline, thiophene worm piperazine, thiophene worm amine, MTI-446, clothianadin, Da Tenan, diflubenzuron, the young urea that goes out, Teflubenzuron, deinsectization are grand, fluorine bell urea, WL 115110, pyridine worm are grand, Acarus tritici urea, poisonous insect urea, penfluron, Noviflumuron are noviflumuron, its CAS number for 121451-02-3, flucycloxuron, Novaluron be Rimon, fluorine pyridine urea, Bay sir 6874 promptly { 1-[(3.5-two chloro-4) 4-nitrophenoxy phenyl 3-3-(2-chlorobenzene)-urea }, Bay SIR-8514 promptly [1-(4-Trifluoromethoxyphen-l)-3-(2-chlorobenzene)-urea], piperazine worm urea, promptly two three WL 115110s of Bistrifluron, furans worm hydrazides, worm hydrazides, chlorine worm hydrazides, methoxyfenozide, ring worm hydrazides, Rogor, omethoate, SD-1750, acephate, triazophos, Resitox, pyridaphenthione, isazofos, Ro 7-5050, SevinCarbaryl, PP-062, MTMC, isoprocarb, cartap, fenobucarb, leaf disperse, one or more medicaments in the carbaryl, benfuracarb, carbosulfan, cartap, bromopropylate, hexythiazox, azoles mite ester, pyridaben, four mite piperazines, alkynes mite spy, butyl ether urea, benfuracarb, pyrrole aphid ketone, spiral shell mite ester, spiral shell worm ester, spiral shell worm ethyl ester, butene-fipronil, azocyclotin, PP618, ethoprophos, fluorine worm nitrile, desinsection list, disosultap, chlorine insect amide, Flubendiamide, fluorine cyanogen insect amide, cyanogen insect amide, azoles insect amide, tebufenpyrad, bromothalonil, pyrazine ketone, second mite azoles, tebufenpyrad, the young ketone of rattling away, pyrrole propyl ether, emaricin mix the purposes of using in preparing sterilant; The described 4-of claim 1 (4-methyl isophthalic acid; 2; 3-thiadiazoles-5-yl)-the total quality percentage composition of 3-alkene-2-ketone V in compsn is 1%-90%; The ratio of the described 4-of claim 1 (4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-3-alkene-2-ketone V and said medicament is mass percent 1%: 99% to 99%: 1%; The formulation of compsn is selected from sustained release dosage; Pulvis; Micro-capsule suspension; The dispersible body preparation; The dispersible solid preparation; Seed treatment emulsion; Aqueous emulsion; Big granula; Microemulsion; Suspended emulsion agent; Water-soluble granule; Soluble thick agent; Water-dispersible granules; Poison grain; Aerosol; Block poison bait; Sustained-release block; Dense poison bait; The capsule granula; Capsule suspension; Dry mixing kind pulvis; Missible oil; The electrostatic spray agent; Water-in-oil emulsion; Oil-in-water emulsion; Smoke candle; Granula subtilis; Smoke candle; Smoke cartridge; The smog rod; The seed treatment suspension agent; The smog sheet; Smoke substance; The smog ball; Granular poison bait; Foaming agent; The drift pulvis; Ointment; Thermal fog; Solid-liquid mixes the dress agent; Liquid/liquid mixes the dress agent; Cold mist agent; Gu Gu/mix and adorn agent; The medicine lacquer; Microgranules; Oil suspending agent; The oil-dispersing property pulvis; Paste; The sheet poison bait; Dense jelly; Sprinkle and water agent; Stylus; Plant the clothing agent; Poison bait; Basting agent; The fritter poison bait; Suspension emulsion; The film forming finish; Soluble powder; The seed treatment water solube powder; The ultra-low volume suspension agent; Tablet; Follow the trail of pulvis; Ultra low volume liquids; The steam releasing agent; In the wet-mixing kind water-dispersible powder any one; The plant that compsn is suitable for is selected from paddy, wheat, barley, oat, corn, Chinese sorghum, sweet potato, yam, cassava, soybean, broad bean, pea, mung bean, red bean, cotton, silkworm and mulberry, peanut, rape, sesame, Sunflower Receptacle, beet, sugarcane, coffee, cocoa, genseng, the bulb of fritillary, rubber, coconut, oil palm, sisal hemp, tobacco, tea, bamboo shoots, hops, pepper.

Of claim 1, wherein the 4 - (4 - methyl-1, 2,3 - thiadiazol-5 - yl) -3 - en-2 - one V with a agriculturally acceptable adjuvants as well as selected Since benzo thiadiazole, thiazole acid bacteria amine, methyl amine induced thiophene 4 - methyl-1, 2,3 - thiadiazole-5 - carboxylic acid 4 - methyl-1, 2,3 - thiadiazole -5 - Sodium 4 - methyl-1, 2,3 - thiadiazole-5 - Ethyl 4 - (bromomethyl) -1,2,3 - thiadiazole-5 - Ethyl 4 - iodomethyl-1, 2,3 - thiadiazole-5 - Ethyl 4 - bromo-5 - methyl-1, 2,3 - thiadiazole-4 - iodo-5 - methyl -1 ,2,3 - thiadiazole, 4,4 - dibromo-1 ,2,3 - thiadiazole-5 - carboxylic acid ethyl ester, DL-β-aminobutyric acid, ribavirin, Antoine Fen, Ningnanmycin or salicylic acid, Cytosinpeptidemycin, dichloro-isonicotinic acid, allyl isothiazole, Isotianil, Cymoxanil, thiram, ziram, mancozeb, fosetyl , thiophanate-methyl, chlorothalonil, the enemy can be loose, procymidone, Fenpropidine, thiophanate, thiophanate, metalaxyl, salicylic acid, flumorph, Dimethomorph, efficient metalaxyl, benalaxyl efficient, bis cypermethrin bacteria amine, flusulfamide, flusulfamide methyl, thiophene amine fluoride bacteria, flutolanil, leaf blight phthalate, cyclopropane amino acid bacteria, cyflufenamid, ring acid bacteria amine, cyano bacteria amine, amine silica thiabendazole, furosemide topiramate amine bacteria, penthiopyrad, diacetylene amine acid bacteria, zoxamide, ofurace, carboxin, acetic bacteria Lee, iprodione, azoxystrobin esters, ethers, amines bacteria, fluoxastrobin, kresoxim-methyl, phenoxy bacteria amine, oxime ether amines bacteria, picoxystrobin, pyraclostrobin, trifloxystrobin, enestroburin, allyl amine trifloxystrobin, oxygen propiconazole, bromuconazole, cyproconazole, difenoconazole azole, Diniconazole, efficient diniconazole, Epoxiconazole, fenbuconazole, fluorine quinazoline, Flusilazole, Flutriafol, Hexaconazole , imide azole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, PTFE Difenoconazole, triadimenol, sterilization yl , Bitertanol, thiabendazole, fuberidazole, imazalil, efficient imazalil, prochloraz, triflumizole, Cyazofamid, imidazole cycloheximide, evil imidazole, pefurazoate, oxazole bacteria ketones, pyridine bacteria oxazole, hymexazol oxadixyl, thiophene pyraclostrobin, earth benomyl, Xin chlorthalidone, benzoth thiocyanate, twelve tridemorph, fenpropimorph, tridemorph, dressing slightly, fludioxonil, fluazinam, piperidine oxime plaque, bacteria amine piperidine ring, boscalid, fluorine boscalid, piperidine amine bacteria, cyprodinil, mepanipyrim fluorine, ferimzone, azoxystrobin amine, pyrimethanil, fenarimol, nuarimol, Chinomethionate, dithianon, ethoxyquin, hydroxyquinoline, quinoline propoxy, phenoxy quinoline, diethofencarb, isopropyl bacteria amines, benzene thiabendazole amines Propamocarb, sulfur bacteria Granville, edifenphos, iprobenfos, topiramate bacteria phosphorus, tolclofos, blasticidin, kasugamycin, polymyxin, more oxygen neomycin, validamycin, Jinggangmycin, streptomycin, metalaxyl, furalaxyl, Benalaxyl, furosemide amide, mepronil, carbendazim, benomyl, thiophanate-methyl, triazole ketones, ethirimol sulfonate, dimethyl ethyl phenol, ethirimol, captafol, captan, folpet, vinclozolin, chlorofluorocarbons sclerotia Lee, Dimetachlone, chlorothalonil, rice Isoprothiolane, kitazine, leaf blight, PCNB, mancozeb, Propineb, fosetyl-aluminum, sulfur, Bordeaux mixture, copper sulfate, copper oxychloride, cuprous oxide, hydrogen copper oxide, benzene cycloheximide, Pencycuron, da cycloheximide, tetrachlorophthalide, pyroquilon, Spiro bacteria amines, Tricyclazole, triforine, more fruit pyridine, Iminoctadine salt Iminoctadine amine, chlorine ammonium nitrate, flusulfamide benzene, toluene, flusulfamide, indole ester, Fenaminosulf, oxolinic acid, allyl benzene, thiazole, bronopol, methyl iodide, metham, enemy lines esters, dazomet, dichloro isopropyl ether, Fosthiazate, Cadusafos, fensulfothion, insects fenamiphos, fenamiphos, Ethoprophos, in addition to line phosphorus, chlorine triazophos, carbosulfan cyclophosphamide, oxamyl, aldicarb Kebai Wei, sulfuryl fluoride, dichloropropene in any one or combination of the two agents for the preparation of fungicides and their use in the control of plant diseases; composition is suitable for a plant selected from rice, wheat, barley, oats, maize , sorghum, sweet potato, potato, cassava, beans, beans, peas, green beans, red beans, cotton, sericulture, peanut, rapeseed, sesame, sunflower, sugar beet, sugar cane, coffee, cocoa, ginseng, Fritillaria, rubber, coconut, oil palm , sisal, tobacco, tea, bamboo shoots, hops, pepper; compositions for diseases selected from Alternaria solani, Botrytis cinerea fungus, peanut leaf spot fungus, Fusarium graminearum, Phytophthora infestans, apple piricola , Rhizoctonia solani, Sclerotinia sclerotiorum, Rhizoctonia cereal plant diseases caused; claim 1, 4 - (4 - methyl-1, 2,3 - thiadiazole-5 - yl) -3 - ene-2 - one V in the composition in a proportion of 1% -90% weight percentage, selected from a sustained release dosage form of the composition, powder, microcapsule suspensions, dispersible liquid formulations, dispersible solid formulation , seed treatment, emulsions, aqueous emulsion, large granules, micro-emulsion, suspension emulsion, a water-soluble granule, soluble concentrate agent, water dispersible granules, poison Valley, aerosols, block bait, release block, concentrated bait, capsules granules, capsules suspensions, dry dressing powders, emulsifiable concentrates, electrostatic sprays, oil-in-water emulsions, water-in-oil emulsion, aerosol cans, fine granules, smoke candle, smoke cartridges, smoke stick, seed treatment, suspension, Smoke tablets, aerosols, smoke pellets, granular baits, made gas agent, rafting powder, ointment, thermal fogging agent, solid / liquid mixing device agent, liquid / liquid mixing device agent, fog agent, solid / solid mixing device agent , medicine paint, particles, oils suspending agents, oil dispersible powders, creams, flaky baits, thick glue, sprinkling agents, stick agents, seed coating, bait, liniment, small baits, suspended emulsion, as membrane oil, soluble powders, water soluble powders for seed treatment, ultra low volume suspension, tablet, tracking powder, ultra low volume liquid, vapor release agents, water-dispersible powder wet dressing of any one.

The described 4-of claim 1 (4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-3-alkene-2-ketone V and agricultural go up acceptable assistant and be selected from diazosulfide, tiadinil, 4-methyl isophthalic acid; 2,3-thiadiazoles-5-formic acid, 4-methyl isophthalic acid, 2; 3-thiadiazoles-5-sodium formiate, 4-methyl isophthalic acid, 2,3-thiadiazoles-5-ethyl formate, 4-brooethyl-1; 2,3-thiadiazoles-5-ethyl formate, 4-iodomethyl-1,2; 3-thiadiazoles-5-ethyl formate, 4-brooethyl-5-methyl isophthalic acid, 2,3-thiadiazoles, 4-iodomethyl-5-methyl isophthalic acid; 2,3-thiadiazoles, 4,4-dibromo methyl isophthalic acid; 2,3-thiadiazoles-5-ethyl formate, DL-beta-aminobutyric acid, virazole, antofine, Ningnanmycin, first thiophene lure any one or the two kinds of medicament combined preparation in amine or Whitfield's ointment, cytosintetidemycin, dichloro-isonicotinic acid, allyl isothiazole, the different metsulfovax to become anti-plant virus agent or plant activator and prevent and treat the purposes of phytopathy in poisoning at Antiphytoviral disease or inducing plant; The described 4-of claim 1 (4-methyl isophthalic acid; 2; 3-thiadiazoles-5-yl)-the total quality percentage composition of 3-alkene-2-ketone V in compsn is 1%-90%; The ratio of the described 4-of claim 1 (4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-3-alkene-2-ketone V and above-mentioned medicament is mass percent 1%: 99% to 99%: 1%; The formulation of compsn is selected from sustained release dosage; Pulvis; Micro-capsule suspension; The dispersible body preparation; The dispersible solid preparation; Seed treatment emulsion; Aqueous emulsion; Big granula; Microemulsion; Suspended emulsion agent; Water-soluble granule; Soluble thick agent; Water-dispersible granules; Poison grain; Aerosol; Block poison bait; Sustained-release block; Dense poison bait; The capsule granula; Capsule suspension; Dry mixing kind pulvis; Missible oil; The electrostatic spray agent; Water-in-oil emulsion; Oil-in-water emulsion; Smoke candle; Granula subtilis; Smoke candle; Smoke cartridge; The smog rod; The seed treatment suspension agent; The smog sheet; Smoke substance; The smog ball; Granular poison bait; Foaming agent; The drift pulvis; Ointment; Thermal fog; Solid-liquid mixes the dress agent; Liquid/liquid mixes the dress agent; Cold mist agent; Gu Gu/mix and adorn agent; The medicine lacquer; Microgranules; Oil suspending agent; The oil-dispersing property pulvis; Paste; The sheet poison bait; Dense jelly; Sprinkle and water agent; Stylus; Plant the clothing agent; Poison bait; Basting agent; The fritter poison bait; Suspension emulsion; The film forming finish; Soluble powder; The seed treatment water solube powder; The ultra-low volume suspension agent; Tablet; Follow the trail of pulvis; Ultra low volume liquids; The steam releasing agent; In the wet-mixing kind water-dispersible powder any one; The plant that compsn is suitable for is selected from paddy, wheat, barley, oat, corn, Chinese sorghum, sweet potato, yam, cassava, soybean, broad bean, pea, mung bean, red bean, cotton, silkworm and mulberry, peanut, rape, sesame, Sunflower Receptacle, beet, sugarcane, coffee, cocoa, genseng, the bulb of fritillary, rubber, coconut, oil palm, sisal hemp, tobacco, tea, bamboo shoots, hops, pepper; The phytopathy that compsn is suitable for is poisoned and is selected from tobacco mosaic virus disease and chilli pepper mosaic virus disease.