CN107226812A - One class piperidines thiazole oxime ether methoxy base acrylate derivative and its production and use - Google Patents

One class piperidines thiazole oxime ether methoxy base acrylate derivative and its production and use Download PDF

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Publication number
CN107226812A
CN107226812A CN201610186472.XA CN201610186472A CN107226812A CN 107226812 A CN107226812 A CN 107226812A CN 201610186472 A CN201610186472 A CN 201610186472A CN 107226812 A CN107226812 A CN 107226812A
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piperidines
thiazole
compound
oxime ether
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范志金
陈来
张秩鸣
郭晓凤
朱玉洁
钱晓琳
马刘勇
徐京华
宋胤奇
李吉宏
张毅超
梁福起
田海丰
于茂祥
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Nankai University
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Nankai University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

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  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The invention provides class piperidines thiazole oxime ether methoxy base acrylate derivative and its production and use, the present invention relates to thiazole oxime ether methoxy base acrylate derivative, they have the chemical structure of general formula as shown in V.

Description

One class piperidines thiazole oxime ether methoxy base acrylate derivative and preparation method thereof and Purposes
Technical field
Technical scheme is related to containing piperidines thiazole oxime ether methoxy base acrylic ester compounds of the N containing S, specifically relates to And piperidines thiazolone, aldehydes oxime ether compound, i.e. piperidines thiazolone, aldehydes oxime ether methoxy base acrylate derivative.
Background technology
It is most of that there is heterocycle structure in the bioactive compound of patent literature；Five member ring heterocyclic compound has Activating plants agent, bactericide, activity (the Chen Dan duckweed moderns, 2014,14 (2) of plant growth regulator and insecticide：5- 10), wherein, thiadiazoles is five yuan of important nitrogenous sulfur heterocyclic compounds, has the kind such as cotton of commercialization in agriculture field Defoliant Thidiazuron, activating plants agent sheet and thiadiazoles (abbreviation BTH) and tiadinil (abbreviation TDL).Class where inventor Topic group is found that first thiophene lures the inducing anti-disease activity of amine and carried out industrialization development, formulates out first, China and has and independently knows Know the activating plants kind of property right, research existing certain report (the Fan Z.J., et of such compound inducing anti-disease activity Al.J.Agric.Food Chem., 2009,57 (10)：4279-4286).
Thiazole derivative has an extensive bioactivity, thiazole derivative have antibacterial, analgesia, anti-inflammatory, it is anticonvulsion, Cardiac stimulant, anticancer, treating tuberculosis and expelling parasite isoreactivity (Sharshiral, E.M., et al.J.Org.Chem., 2012,2 (3)：69- 73.).The pesticide activity of this kind of compound just include desinsection, sterilization, weeding, plant growth regulating, it is antiviral etc. (Chen Caijun, Deng the progress agricultural chemicals of thiazole insecticides, 2005,44 (2)：53-55.).Piperidine alkaloid is distributed widely in plant Boundary, and show multiple biological activities (Richerson.G.B., et al., 2003,90：1363-1374.).Piperidine derivatives Extensive bioactivity, such as bactericide fenpropidin, herbicide dimepiperate, plant growth regulator first are also shown in terms of agricultural chemicals Piperazine etc. all has preferable bioactivity (Jiang Zhigan, et al., Eur.J.Med.Chem, 2014,82：490- 497).The research that active substructure unit thiazole ring and piperidine ring are combined have been reported (Black, Janice.WO2007071900A1；Pasteris, et al., WO2008091580 A2).
Oxime ether derivatives are the compounds that a class has excellent bioactivity, are not only pharmaceutically being had a wide range of applications, It is also the important reactive compound of a class on agricultural chemicals.Relevant oxime ether reactive compound, (Song is precious for existing a large amount of reports both at home and abroad Peace, waits the synthesis of oxime derivatives and the progress organic chemistry of pesticide bioactivity, 2005,25 (5)：507-525.), Also there are many commodity to come out simultaneously, such as effective to downy mildew cymoxanil (cymoxanil), have to northern house and housefly compared with The insect growth regulator, IGR S-21149 and S-21150 of high activity, to pears red spider, citrus red mite activity quite high fenpyroximate (fenpyroximate), there is the propaquizafop of preferable preventive effect to many main annual and perennial grassy weeds (propa quizafop) etc. (model is built, and waits moderns, 2008,7 (2)：6-11.).Oxime ether structure is frequently as good drug effect Group is introduced in parent compound molecule, to improve its bioactivity.
Methoxy acrylic bactericide has the bactericidal activity of wide spectrum, to nearly all Mycophyta (Ascomycetes, load Daughter bacteria guiding principle, Oomycete and Fungi Imperfecti) disease has good activity, such as powdery mildew of wheat class, leaf blight, red spot, filigree Disease, apple scab, the rice blast of paddy rice, banded sclerotial blight and downy mildew and epidemic disease etc. (love jade-like stone finely and specialty chemicals, 2012,20 (4)：24-28).Such medicament possess efficiently, wide spectrum, low toxicity, interior suction and a variety of advantages such as degradable, it is most main as the whole world Disinfectant use in agriculture (Yuan small brave .2014,34 wanted：170-177).In the methoxy acrylic bactericide of viable commercial product Important kind mainly has：Fluoxastrobin (azoxystrobin), kresoxim-methyl (kresoxim-methyl), pyraclostrobin (pyraclostrobin), trifloxystrobin (trifloxystrobin), fluoxastrobin (fluoxastrobin), ZEN 90160 (picoxystrobin), SSF 126 (metaminostrobin), dimoxystrobin (dimoxystrobin), orysastrobin (orysastrobin), Enestroburin (enestrobin), pyraoxystrobin (pyraoxystrobin), alkene oxime amine (SYP-1620) Deng.Because Strobilurin series bactericidal agent action sites are single, a large amount of high frequency high intensities are very prominent using the resistance problem brought Go out (Fisher, N.Pest.Manage.Sci.2005,61 (10)：973-978)；Activating plants agent has the lasting system of spectrum Disease resistance is obtained, pathogen is not directly placed on and acts on plant in itself, be the important directions of 21 century plant protection, such Therefore medicament, formulates more extremely urgent more than efficient medicament without drug-fast risk.
To find and finding more efficient, wide spectrum, low toxicity, low ecological risk and the agricultural chemicals guide of no interactions resistance and candidate Piperidines thiazole is introduced into the guide structure of methoxy acrylate by compound, the present invention, and design has synthesized a class piperidines thiazole Oxime ether methoxy base acrylate derivative, and carried out the screening and evaluation of the bioactivity of system.
The content of the invention
The technical problems to be solved by the invention are：The new piperidines thiazole oxime ether methoxy base acrylate of a class is provided to derive There is provided this kind of compound modulates agricultural, gardening and health and forestry plant insect and the phytopathy original for the synthetic method of thing Bioactivity and its assay method, while providing these compounds in agriculture field, horticultural field, field of forestry and health neck Application in domain.
The present invention solves the technical scheme that is used of the technical problem：With agriculture field, horticultural field, field of forestry Desinsection, acaricidal activity, bactericidal activity, anti-phytoviral activity, induction plant produce the piperidines thiazole oxime ether methoxy of anti-disease activity The chemical structure of general formula of base acrylic ester compound is shown in Formula V：
Wherein, R1It is selected from：Methyl, hydrogen；R2It is selected from：1,2- bis- fluoro ethyl, propargyl, cyclopropyl, methyl, 1- methyl mercaptos -2- Methyl propyl- 2- bases, (R) -1- methyl mercapto propyl- 2- bases；R3It is selected from：Hydrogen, hydrogen chloride；X is selected from：Oxygen, nitrogen, n=1,2；
The synthetic method of 1,2, the 3- piperidines thiazole oxime ether methoxy base acrylate derivatives of the present invention is as follows：
Wherein, R1It is selected from：Methyl, hydrogen；R2It is selected from：1,2- bis- fluoro ethyl, propargyl, cyclopropyl, methyl, 1- methyl mercaptos -2- Methyl propyl- 2- bases, (R) -1- methyl mercapto propyl- 2- bases；R3It is selected from：Hydrogen, hydrogen chloride；X is selected from：Oxygen, nitrogen, n=1,2；
The present invention piperidines thiazole oxime ether methoxy base acrylate derivative synthesis and biological activity determination it is specific Method is divided into following steps：
A. compound II preparation：
1.10 mMs of compound I are added in 25 milliliters of single necked round bottom flask, is dissolved, added with 15 milliliters of ethanol 1.00 mMs of substituted piperidine thiazole carbonyls, the piperidines thiazole carbonyls is selected from：Piperidines thiazolone, piperidines thiophene Two hydrochloric acid for dripping 2 mol/Ls are added dropwise in azoles aldehyde, most backward reaction system, are stirred at room temperature 12 hours, are removed under reduced pressure after reaction completely Solvent, residue purifies to obtain compound II through 200~300 mesh silica gel column chromatographies, and eluant, eluent is 60~90 degrees Celsius of petroleum ether: Ethyl acetate, according to the difference of product, volume ratio is 9: 1-2: 1, yield 40-50%；Amount and reaction prepared by compound II is held The volume of device is expanded or shunk by corresponding proportion.
B. compound III preparation：
0.24 mM of compound II is added in 25 milliliters of single necked round bottom flask, is dissolved with 15 ml methanols, to reaction The middle addition mM sodium hydroxide of 0.03 gram, i.e., 0.72, is then heated to reflux 30 minutes, reaction concentrates reaction solution after terminating, Residue is diluted with 10 milliliters of ethyl acetate, and the water for adding 10 milliliters all dissolves solid, separates water-yielding stratum, water layer is rubbed with 2 You/liter salt acid for adjusting pH to 3, be then extracted with ethyl acetate, aqueous layer with ethyl acetate be stripped one time, merge organic layer, have Machine layer is washed one time with saturated sodium-chloride, and anhydrous sodium sulfate drying, suction filtration, removal of solvent under reduced pressure obtains compound III；Yield 95- 100%；Amount and the volume of reaction vessel prepared by compound III is expanded or shunk by corresponding proportion.
C. compound IV preparation：
0.30 mM of compound III is added in 25 milliliters of single necked round bottom flask, with 15 milliliters of dry dichloromethane Dissolving, the EDCI of 0.69 gram, i.e., 0.36 mM, i.e. 1- ethyls-(3- dimethylaminopropyls) carbon two is added into reaction sub- The HOBT of amine hydrochlorate and 0.43 gram, i.e., 0.32 mM, i.e. 1- hydroxy benzo triazoles, 30 points are stirred at room temperature after adding Clock, then adds 0.32 mM of R into reaction system2-XHn, n=1,2；It is stirred at room temperature 2 hours, after reaction terminates, reaction Liquid isolates organic layer, organic layer respectively washes one with saturated sodium bicarbonate and saturated sodium-chloride respectively with 15 milliliters of twice of washing Time, anhydrous sodium sulfate drying, suction filtration, removal of solvent under reduced pressure, residue obtains white through the purifying of 200~300 mesh silica gel column chromatographies Solid, eluant, eluent is 60~90 degrees Celsius of petroleum ether: ethyl acetate, and volume ratio is 4: 1, yield 60%-95%；Compound IV The amount of preparation and the volume of reaction vessel are expanded or shunk by corresponding proportion.
D. compound V preparation：
0.30 mM of compound IV is added in 25 milliliters of single necked round bottom flask, with 15 milliliters of dry dichloromethane In, the trifluoroacetic acid of 1.5 milliliters of drop under condition of ice bath, addition is finished, is stirred overnight at room temperature, and reaction terminates, with 1 mole every liter Sodium hydroxide is neutralized to PH=7-8, isolates organic layer, and organic layer respectively washes one with saturated sodium bicarbonate and saturated sodium-chloride respectively Time, anhydrous sodium sulfate drying, suction filtration, removal of solvent under reduced pressure, residue obtains white through the purifying of 200~300 mesh silica gel column chromatographies Solid, eluant, eluent is dichloromethane: methanol, and volume ratio is 8: 1, yield 96.26%；Amount and reaction vessel prepared by compound V Volume expanded or shunk by corresponding proportion.
E. piperidines thiazole oxime ether methoxy base acrylate derivative V of the invention bactericidal activity is determined：
The piperidines thiazole oxime ether methoxy base acrylate V of present invention sterilization or bacteriostatic activity are determined using thalli growth rate Method, is concretely comprised the following steps：Take 1.8 milligrams of samples to be dissolved in 2 drop DMFs, then use and contain a certain amount of polysorbas20 The aqueous solution of emulsifying agent is diluted to the medicament of 500 mcg/mls, and reagent agent is aseptically respectively drawn to 1 milliliter in training Support in ware, then be separately added into 9 milliliters of PDA culture mediums, 50 mcg/ml pastille flat boards are made after shaking up, to add 1 milliliter of sterilizing The flat board of water does blank control, cuts bacterium disk along mycelia outer rim with the card punch of 4 millimeters of diameter, moves on pastille flat board, in etc. Side triangle is put, and often processing is repeated 3 times, and culture dish is placed on into culture, bacterium colony to be compareed in 24 ± 1 degrees Celsius of constant incubators Diameter expansion is averaged to each processing bacterium disk extension diameter is investigated after 2-3 centimetres, calculating is compared with blank control relatively antibacterial Rate, is the kind of most of typical plant pathogen that field is actually occurred in China's agricultural production for examination strain, its code name and Title is as follows：AS：Tomato early blight bacterium, its Latin is entitled：Alternaria solani、BC：Botrytis cinerea pers, its Latin It is entitled：Botrytis cinerea、CA：Peanut Cercospora bacteria, its Latin is entitled：Cercospora arachidicola、GZ： Fusarium graminearum, its Latin is entitled：Gibberella zeae、PI：Phytophthora infestans, its Latin is entitled： Phytophthora infestans(Mont.)de Bary、PP：Botryosphaeria berengeriana f. sp, its Latin is entitled：Physalospora piricola、PS：Rhizoctonia solani Kuhn, its Latin is entitled：Pellicularia sasakii、RC：Rhizoctonia cerealis, its Latin It is entitled：Rhizoctonia cerealis、SS：Sclerotinia sclerotiorum, its Latin is entitled：Sclerotinia sclerotiorum。
F. the measure of piperidines thiazole oxime ether methoxy base acrylate derivative V inducing anti-disease activities of the invention：
Piperidines thiazole oxime ether methoxy base acrylate derivative V method for screening active ingredients is as follows, and tobacco mosaic virus (TMV) is write a Chinese character in simplified form For TMV：
(1) positive controls activating plants agent：The tiadinil for selecting quality purity purity to be more than 99.5% is positive control Activating plants agent；Tiadinil is abbreviated as TDL；
(2) screening technique of the anti-TMV activity of piperidines thiazole oxime ether methoxy base acrylate derivative V evoking tobacco：From The measure of the direct antiviral activity of body is carried out using half leaf method；Live body induction is that, by the consistent common cigarette of seedling age, 3 basins are one group, Respectively at the tobacco seedlings for being inoculated with preceding pre-treatment in 7 days, processing mode includes：Spray test compounds solution 2 to 3 times, every time 10 milli Rise, or soil treatment, 10 milliliters every time, measure concentration is 100 mcg/mls, and the 7th day in frictional inoculation on the tobacco leaf newly grown TMV, tobacco seedlings is placed in after being cultivated 3 days under its growth preference temperature and illumination, checks incidence, comprehensive scab number is as the following formula Induction antiviral effect of the test compound to TMV is calculated, each processing sets 3 repetitions, blank control and standard agent pair According to selection water and TDL respectively：
Wherein, R is test compound TMV anti-to tobacco inducing effect, unit：%；CK is that clear water compares the flat of blade Equal withered spot number, unit：It is individual；I is that the average withered spot number for handling rear blade is induced through test compound, unit：It is individual.
The beneficial effects of the invention are as follows：Guide's optimization has been carried out to piperidines thiazole oxime ether methoxy base acrylate derivative V, And the screening of bacteriostatic activity has been carried out to piperidines thiazole oxime ether methoxy base acrylate derivative.
The present invention passes through specific preparation and the more specific explanation piperidines thiazole oxime ether methoxy base of biological activity determination embodiment Acrylate derivative V synthesis and bioactivity and application, the embodiment are only used for illustrating the present invention and unrestricted The present invention, especially bioactivity are merely illustrative of, and unrestricted this patent, and embodiment is as follows：
Embodiment 1：Compound II preparation：
1.10 mMs of compound I are added in 25 milliliters of single necked round bottom flask, is dissolved, added with 15 milliliters of ethanol 1.00 mMs of substituted piperidine thiazole carbonyls, the piperidines thiazole carbonyls is selected from：Piperidines thiazolone, piperidines thiophene Two hydrochloric acid for dripping 2 mol/Ls are added dropwise in azoles aldehyde, final reaction system, are stirred at room temperature 12 hours, are removed under reduced pressure after reaction completely molten Agent, residue purifies to obtain compound II through 200~300 mesh silica gel column chromatographies, and eluant, eluent is 60~90 degrees Celsius of petroleum ether: second Acetoacetic ester, volume ratio is 9: 1, yield 40-50%；Work as R1For methyl, the nuclear magnetic data of the compound is as follows：δ 7.49 (s, 1H, ArH), 7.45-7.35 (m, 3H, ArH), 7.19 (d, J=7.2Hz, 1H, ArH), 5.13 (s, 2H, Ph-CH2), 4.26-4.12 (m, 2H, N-CH2), 4.03 (s, 3H, O-CH3), 3.83 (s, 3H, N-CH3), 3.19 (ddd, J=11.6,8.0,3.7Hz, 1H, Piperidine-H), 2.88 (d, J=11.7Hz, 2H, Piperidine-H), 2.26 (s, 3H, thiadiazole-CH3), 2.09 (d, J=11.5Hz, 2H, Piperidine-H), 1.73-1.67 (m, 2H, Piperidine-H), 1.47 (s, 9H, Boc- H).Amount and the volume of reaction vessel prepared by compound II is expanded or shunk by corresponding proportion.Compound II physical and chemical parameter and Structural parameters are shown in Table 1.
Embodiment 2：Compound III preparation：
0.24 mM of compound II is added in 25 milliliters of single necked round bottom flask, is dissolved with 15 ml methanols, to reaction The middle addition mM sodium hydroxide of 0.03 gram, i.e., 0.72, is then heated to reflux 30 minutes, reaction concentrates reaction solution after terminating, Residue is diluted with 10 milliliters of ethyl acetate, and the water for adding 10 milliliters all dissolves solid, separates water-yielding stratum, water layer is rubbed with 2 You/liter salt acid for adjusting pH to 3, be then extracted with ethyl acetate, aqueous layer with ethyl acetate be stripped one time, merge organic layer, have Machine layer is washed one time with saturated sodium-chloride, and anhydrous sodium sulfate drying, suction filtration, removal of solvent under reduced pressure obtains compound III；Yield 95- 100%；Amount and the volume of reaction vessel prepared by compound III is expanded or shunk by corresponding proportion.Compound III physics and chemistry ginseng Number and structural parameters are shown in Table 1.
Embodiment 3：Compound IV preparation：
0.30 mM of compound III is added in 25 milliliters of single necked round bottom flask, with 15 milliliters of dry dichloromethane Dissolving, the EDCI of 0.69 gram, i.e., 0.36 mM, i.e. 1- ethyls-(3- dimethylaminopropyls) carbon two is added into reaction sub- The HOBT of amine hydrochlorate and 0.43 gram, i.e., 0.32 mM, i.e. 1- hydroxy benzo triazoles, 30 points are stirred at room temperature after adding Clock, then adds 0.32 mM of R into reaction system2-XHn, n=1,2；It is stirred at room temperature 2 hours, after reaction terminates, reaction Liquid isolates organic layer, organic layer respectively washes one with saturated sodium bicarbonate and saturated sodium-chloride respectively with 15 milliliters of twice of washing Time, anhydrous sodium sulfate drying, suction filtration, removal of solvent under reduced pressure, residue purifies white solid through 200~300 mesh silica gel column chromatographies Body IV, eluant, eluent is 60~90 degrees Celsius of petroleum ether: ethyl acetate, and volume ratio is 4: 1, yield 60%-90%；Work as R1For first Base, R2For cyclopropyl, the nuclear magnetic data of the compound is as follows：δ 7.47 (d, J=7.2Hz, 1H), 7.43 (s, 1H), 7.39- 7.33 (m, 2H), 7.19 (d, J=7.3Hz, 1H), 6.90 (d, J=2.5Hz, 1H), 5.12 (s, 2H), 4.18 (s, 2H), 3.91 (s, 3H), 3.19 (t, J=11.5Hz, 1H), 2.86 (s, 2H), 2.81-2.72 (m, 1H), 2.26 (s, 3H), 2.09 (d, J= 12.1Hz, 2H), 1.70 (d, J=12.0Hz, 2H), 1.47 (s, 9H), 0.76 (d, J=6.9Hz, 2H), 0.56 (s, 2H).Change Amount and the volume of reaction vessel prepared by compound IV is expanded or shunk by corresponding proportion.Compound IV physical and chemical parameter and structure ginseng Number is shown in Table 1.
Embodiment 4：Compound V preparation：
0.30 mM of compound IV is added in 25 milliliters of single necked round bottom flask, with 15 milliliters of dry dichloromethane In, the trifluoroacetic acid of 1.5 milliliters of drop under condition of ice bath, addition is finished, is stirred overnight at room temperature, and reaction terminates, with 1 mole every liter Sodium hydroxide is neutralized to PH=7-8, isolates organic layer, and organic layer respectively washes one with saturated sodium bicarbonate and saturated sodium-chloride respectively Time, anhydrous sodium sulfate drying, suction filtration, removal of solvent under reduced pressure, residue obtains white through the purifying of 200~300 mesh silica gel column chromatographies Solid, eluant, eluent is dichloromethane: methanol, and volume ratio is 8: 1, yield 96.26%；Amount and reaction vessel prepared by compound V Volume expanded or shunk by corresponding proportion.Compound V physical and chemical parameter and structural parameters is shown in Table 1.
Embodiment 5：Compound CL05-00 preparation method：
1.10 mMs of compound b are added in 25 milliliters of single necked round bottom flask, is dissolved, added with 15 milliliters of ethanol Two hydrochloric acid for dripping 2 mol/Ls are added dropwise in 1.00 mMs of a, final reaction system, are stirred at room temperature 12 hours, subtract after reaction completely Pressure removes solvent, and residue purifies to obtain compound CL05-00 through 200~300 mesh silica gel column chromatographies, and eluant, eluent is 60~90 Celsius The petroleum ether: ethyl acetate of degree, volume ratio is 4: 1, yield 63.12%.
Embodiment 6：The piperidines thiazole oxime ether methoxy base acrylate derivative V of present invention Antibacterial Activity result：
The code name and title for the frequently seen plants disease fungus that the present invention is tested are as follows：AS：Tomato early blight bacterium, its latin name For：Alternaria solani、BC：Botrytis cinerea pers, its Latin is entitled：Botrytis cinerea、CA：Peanut foxiness Germ, its Latin is entitled：Cercospora arachidicola、GZ：Fusarium graminearum, its Latin is entitled：Gibberella zeae、PI：Phytophthora infestans, its Latin is entitled：Phytophthora infestans(Mont.)de Bary、PP：Apple Fruit Target spot pathogen, its Latin is entitled：Physalospora piricola、PS：Rhizoctonia solani Kuhn, its Latin is entitled： Pellicularia sasakii、RC：Rhizoctonia cerealis, its Latin is entitled：Rhizoctonia cerealis、SS：Sclerotina Sclerotiorum in Winter Rape Core germ, its Latin is entitled：Sclerotinia sclerotiorum, these strains have good representativeness, can represent The kind for most of pathogen that field occurs in agricultural production.
It is worth noting that compound CL05-00 is the chemistry reported in the A1 of patent WO 2000003974 in the present invention Structure and the immediate known compound of target compound of the present invention, in order to which the biology of the noval chemical compound relatively more of the invention synthesized is living Property, it is of the invention to have synthesized structure closest to the known compound CL05-00 of target compound of the present invention as control compound, and Expression activitiy is carried out with target compound of the present invention.
Thalli growth rate method measurement result is shown in Table 2, and table 2 shows, in 50 mcg/ml, allization that the present invention is synthesized Compound has different degrees of bactericidal activity.For tomato early blight bacterium, compound CL04-43A, CL04- of the invention 43B, CL04-45D, CL05-15 inhibiting rate reach more than 40%, and the bactericidal activity of above-claimed cpd is higher by document report With the immediate compound CL05-00 more than 20% of target compound chemical constitution of the present invention, wherein compound CL04-43B's Bactericidal activity reaches 45.45%；For peanut Cercospora bacteria, compound CL04-43A, CL04-43B, CL04-45A, CL04-45B, CL04-45C, CL04-45D, CL05-15 bactericidal activity are more than 30%, the bactericidal activity of above-claimed cpd Be higher by document report with the immediate compound CL05-00 more than 10% of target compound chemical constitution of the present invention, wherein Compound CL04-43A, CL04-43B, CL04-45D, CL05-15 bactericidal activity are more than 50%, with the phonetic bacterium of comparison medicine Ester is suitable, wherein compound CL04-45D inhibiting rates highest, up to 58.33%；Activity for fusarium graminearum shows, chemical combination Thing CL04-43A, CL04-45B, CL04-45C, CL04-45D and CL05-15 inhibiting rate are more than 40%, above-claimed cpd Bactericidal activity be higher by document report with the immediate compound CL05-00 of target compound chemical constitution of the present invention More than 30%, wherein compound CL04-45B bactericidal activity highest, up to 57.58%；For Botryosphaeria berengeriana f. sp, compound CL04-43A, CL04-45B, CL04-45C, CL04-45D and CL05-15 inhibiting rate more than 50%, above-claimed cpd Bactericidal activity be higher by document report with the immediate compound CL05-00 30% of target compound chemical constitution of the present invention More than, and compound CL04-45C inhibiting rate highest, up to 56.30%；For botrytis cinerea pers, compound CL04- 43A, CL04-43B, CL04-45A, CL04-45B, CL04-45C, CL04-45D, CL04-45E and CL05-15 inhibiting rate are equal More than 40%, the bactericidal activity of above-claimed cpd is higher by most being connect with target compound chemical constitution of the present invention for document report Near compound CL05-00 more than 10%, and compound CL04-43A, CL04-43B and CL05-15 inhibiting rate 70% More than, wherein compound CL04-43A and CL05-15 bactericidal activity highest, up to 75.00%；For Sclerotinia sclerotiorum Speech, compound CL04-43A, CL04-43B, CL04-45A, CL04-45B, CL04-45D and CL05-15 bactericidal activity exists More than 40%, the bactericidal activity of above-claimed cpd is higher by the closest with target compound chemical constitution of the present invention of document report Compound CL05-00 more than 10%, wherein compound CL04-45B and CL04-45D inhibiting rate highest, up to 64.71%； For Rhizoctonia cerealis, compound CL04-43A, CL04-43B, CL04-45A, CL04-45B, CL04-45C, CL04- 45D, CL04-45E and CL05-15 bactericidal activity are more than 30%, and the bactericidal activity of above-claimed cpd is higher by document report Road with the immediate compound CL05-00 more than 30% of target compound chemical constitution of the present invention, wherein compound CL04- 43A, CL04-43B, CL04-45B, CL04-45D and CL05-15 bactericidal activity are more than 70%, and compound CL04- 43A, CL04-43B, CL04-45B and CL05-15 bactericidal activity highest, up to 78.00%；To the active table of Rhizoctonia solani Kuhn It is bright, compound CL04-43A, CL04-43B, CL04-45A, CL04-45B, CL04-45C, CL04-45D and CL05-15 sterilization Activity is more than 30%, and the bactericidal activity of above-claimed cpd is higher by being tied with target compound of the present invention chemistry for document report Structure immediate compound CL05-00 more than 10%, wherein compound CL04-43A, CL04-45D and CL05-15 sterilization are lived Property is more than 50%, and bactericidal activity highest, up to 54.55%；For phytophthora infestans, compound CL04- 43A, CL04-43B, CL04-45B, CL04-45D and CL05-15 bactericidal activity are more than 40%, and above-claimed cpd is killed Bacterium activity be higher by document report with the immediate compound CL05-00 20% of target compound chemical constitution of the present invention with On, wherein compound CL04-43A, CL04-43B, CL04-45D and CL05-15 bactericidal activity is above comparison medicine Fluoxastrobin, And compound CL04-43A bactericidal activity highest, up to 62.86%；It can to sum up obtain, above-mentioned majority of compounds is respectively provided with extensively The bactericidal activity of spectrum.
Be shown in Table 3, table 3 shows, all compounds for synthesizing of the present invention have different degrees of bactericidal activity, 400 micrograms/ During milliliter, for cucumber downy mildew, compound CL04-43A, CL04-43B, CL04-45A, CL04-45B and CL04-45D Inhibiting rate more than 70%, the bactericidal activity of above-mentioned compound is being higher by document report with target compound of the present invention The immediate compound CL05-00 more than 40% of chemical constitution, wherein compound CL04-45B bactericidal activity and comparison medicine is phonetic The activity of bacterium ester is the same, up to 85%；For wheat powdery mildew, compound CL04-43A, CL04-45D and CL05-15's kills Bacterium activity is 100%, and the bactericidal activity of above-mentioned compound is higher by the chemical with target compound of the present invention of document report The immediate compound CL05-00 more than 70% of structure, as the bactericidal activity of comparison medicine Fluoxastrobin；For corn rust For, compound CL04-43A, CL04-43B, CL04-45D and CL05-15 inhibiting rate are more than 70%, above-mentioned chemical combination The bactericidal activity of thing be higher by document report with the immediate compound CL05-00 of target compound chemical constitution of the present invention More than 40%, comparison medicine Fluoxastrobin, and compound CL05-15 bactericidal activity highest are above, up to 100%；For watermelon charcoal Subcutaneous ulcer disease for, compound CL04-43A, CL04-43B, CL04-45C and CL04-45D bactericidal activity more than 70%, on The bactericidal activity for the compound stated is being higher by document report with the immediate compound of target compound chemical constitution of the present invention CL05-00 more than 50%, and the bactericidal activity of compound CL04-43B, CL04-45C is suitable with comparison medicine Fluoxastrobin；It is micro- 25 During grams per milliliter, for rice blast, compound CL04-43A, CL04-43B, CL04-45A, CL04-45B, CL04- 45C, CL04-45D and CL05-15 bactericidal activity are more than 80%, and the bactericidal activity of above-mentioned compound is higher by document Report with the immediate compound CL05-00 more than 40% of target compound chemical constitution of the present invention, wherein compound CL04-43A, CL04-45B and CL04-45D bactericidal activity are above comparison medicine Fluoxastrobin more than 10% more than 90%, And compound CL04-43A and CL04-45B bactericidal activity highest, up to 100%；For gray mold of cucumber, compound CL05-15 inhibiting rate reaches 100%, and the bactericidal activity of above-mentioned compound is being higher by document report with target chemical combination of the present invention The immediate compound CL05-00 90% of chemical structure and comparison medicine Fluoxastrobin more than 50%, in summary, compound CL04-43A and CL05-15 have the bactericidal activity of wide spectrum.
Embodiment 7：The piperidines thiazole oxime ether methoxy base acrylate derivative IV of present invention resisting tobacco mosaic virus (TMV) it is active：
The measurement result of TMV activity is shown in Table 4, and table 4 shows, majority of compounds of the invention has preferable anti-TMV's Activity；In 100 mcg/ml, all compounds that the present invention is synthesized have different degrees of anti-TMV activity.In treatment mould Under formula, compound CL04-43B, CL04-45D and CL04-45F therapeutic activity is being higher by document report with targeted of the present invention The immediate compound CL05-00 more than 30% of compound chemical constitution, although less than comparison medicine Ningnanmycin, but still have There is preferable therapeutic effect；Under passivation pattern, compound CL04-43A, CL04-45F and CL05-15 passivation inhibiting rate exist More than 20%, the passivation activity of above-claimed cpd is higher by the closest with target compound chemical constitution of the present invention of document report Compound CL05-00 more than 10%, although less than comparison medicine virazole, but be demonstrated by preferably passivation activity；Protecting Under shield pattern, compound CL04-43A, CL04-43B, CL04-45A, CL04-45B, CL04-45C, CL04-45D, CL04- 45E, CL04-45F and CL05-15 protection activity are more than 30%, and the protection activity of above-claimed cpd is higher by document report Road with the immediate compound CL05-00 more than 10% of target compound chemical constitution of the present invention, wherein CL04-43B guarantor The active highest of shield, up to 53.79%, although less than comparison medicine BTH, but is demonstrated by preferably passivation activity；In induction pattern Under, compound CL04-43A, CL04-43B, CL04-45A, CL04-45C, CL04-45D, CL04-45E and CL04-45F's lures Activity is led more than 40%, the induced activity of above-claimed cpd is higher by the chemical with target compound of the present invention of document report The immediate compound CL05-00 more than 30% of structure, wherein compound CL04-45C induced activity highest, reach 74.89%, it is suitable with comparison medicine TDL, BTH, SZG-7；It can be seen that, majority of compounds of the invention has anti-TMV work well Property.
The piperidines thiazole oxime ether methoxy base acrylate derivative IV of the present invention is also to rice dwarf virus disease, BYDV, striped Leaf blight, fern leaf of tomato viral disease, pepper mosaic virus disease viral disease, tobacco veinal necrosis virus disease, maize dwarf mosaic, Cauliflower Mosaic Virus, citrus virosis, cymbidium mosaic virus disease, the agricultural of cybidium ring spot virus and forestry and gardening plant virus disease tool There is good antiviral activity.
Embodiment 8：The piperidines thiazole oxime ether methoxy base acrylate derivative V of the present invention is with insecticide composition in preventing and treating agriculture Application in industry and forestry and gardening plant insect pest：
All piperidines thiazole oxime ether methoxy base acrylate derivative V of the present invention and any one in commodity insecticide Or two kinds of combinations form Pesticidal combination and are used to prevent and treat agricultural and forestry and gardening plant insect pest, the commodity insecticide choosing From：Chlopyrifos, Asia Nong, Acetamiprid, emamectin benzoate, milbemectin, AVM, pleocidin, fenvalerate, height Imitate fenvalerate, cypermethrin, effective cypermethrin, Cyhalothrin, decis, Fenpropathrin, Beta- cyfluthrin chrysanthemums Ester, Lambda- Cyhalothrins, Permanone, permethrin, allethrin, Biphenthrin, Permethrin, ethofenprox, Flumethrin, fluvalinate, imidacloprid, Nitenpyram, imidaclothiz, thiacloprid, Diacloden, clothianidin, MTI-446, Clothianadin, Da Tenan, diflubenzuron, d ichlorbenzuron, Teflubenzuron, grand deinsectization, HEXAFLUMURON, flufenoxuron, grand pyridine worm, lufenuron, poisonous insect urea, Penfluron, Noviflumuron are noviflumuron, its No. CAS be 121451-02-3, flucycloxuron, Novaluron be Rimon, Chlorfluazuron, Bay sir 6874 are 1- [(3.5- bis- chloro- 4) 4-nitrophenoxy phenyl 3-3- (2- chlorobenzenes)-urea, Bay SIR- 8514 i.e. 1- (4- Trifluoromethoxyphen-ls) -3- (2- chlorobenzenes)-urea, piperazine worm urea, Bistrifluron is bistrifluron, furans Tebufenozide, tebufenozide, chlorine tebufenozide, methoxyfenozide, ring tebufenozide, Rogor, flolimat, DDVP, orthene, three Azoles phosphorus, quinalphos, pyridaphethione, isazofos, isoprocarb, sevin, Aphox, MTMC, Mobucin, cartap, Bassa, Leaf disperses, carbaryl, Benfuracard micro, carbosulfan, cartap, fenisobromolate, Hexythiazox, fenpyroximate, pyridaben, four mites Piperazine, propargite, diafenthiuron, pymetrozine, Envidor, spiral shell worm ester, spiral shell worm ethyl ester, butene-fipronil, azacyclotin, Buprofezin, go out line Phosphorus, ethiprole, Cupric sulfate, dimehypo, chlorantraniliprole, Flubendiamide, fluorine cyanogen insect amide, cyanogen insect amide, Tolfenpyrad, bromine worm Nitrile, pyrazinones, etoxazole, tebufenpyrad, rattle away young ketone, Nylar, emaricin；The piperidines thiazole oxime ether methoxy base propylene of the present invention Weight/mass percentage compositions of the acid ester derivant V in the Pesticidal combination is 1%-90%, piperidines thiazole oxime ether first of the invention The ratio of epoxide acrylate derivative V and foregoing commodity insecticide is mass percent 1%: 99% to 99%: 1%；It is described The formulation of Pesticidal combination processing is selected from：Seed treatment emulsion, aqueous emulsion, microemulsion, suspension emulsion, capsule suspension, water solubility Granula, granula subtilis, soluble thick agent, poison grain, block poison bait, granular poison bait, sheet poison bait, dense poison bait, sustained-release block, electrostatic spray It is agent, oil in water emulsion, smoke candle, smoke candle, smoke cartridge, smog rod, smog piece, smog ball, foaming agent, ointment, thermal fog, cold Gu mist agent, aerosol, the agent of solid-liquid mixing dress, liquid liquid mix dress agent, solid/mixing dress agent, medicine paint, fine granule, tracking pulvis, oil Suspension, oil-dispersing property pulvis, dense jelly, sprinkle pour agent, seed coat agent, liniment, film forming finish, ultra low volume liquids, steam release Agent；The insect pest of the plant of the Pesticidal combination preventing and treating is selected from：Red spider, Asiatic migrotory locust, reading room management, Chinese rice grasshopper, Japan are yellow Ridge locust, single thorn mole cricket, Oriental burmeister, rice thripses, onion thrips, greenhouse thrips, haplothrips aculeatus, Mai Jian pipes 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 plant hopper of sugarcane, Cotten aphid, green bugs, grain aphid, black peach aphid, kaoliang aphid, radish aphid, icerya purchasi, Pseudaulacaspis pentagona, unaspis shield kuwana, san jose scale, Chinese wax Worm, ceroplastes rubens, Didesmococcus koreanus Borchs, pear lace bug, banana lace bug, thin corner piece stinkbug, Orius minutus, slender rice bug, paddy fly, rice are brown Stinkbug, scotinophora lurida, green rice bug, green plant bug, alfalfa plant bug, black striped plant bug, chrysopa septempunctata, beautiful Chrysopa, Chinese green lacewing, rain moth, casemaking clothes moth, Huang The small food of slug moth, brown slug moth, thosea siensis, gelechiid, pink bollworm, brachmia triannuella, diamondback moth, small heart-eating peach worm, eating-core bean worm, peach Heart worm, apple Spilonota lechriaspis, brown belt length leaf roller, Adoxophyes cyrtosema, striped rice borer, bean-pod borer, corn borer, yellow rice borer, dish Snout moth's larva, rice leaf roller, bar snout moth's larva, Notarchaderogata, dichocrocis punctiferalis, armyworm, prodenia litura, rice green caterpillar, anomis flava, beet night Moth, pink rice borer, bollworm, ancient cooking vessel point spark, black cutworm, big cutworm, yellow cutworm, steal poison moth, gypsymoth, palaearctic sweet potato, The yellow a kind of butterfly harmful to crop plants of greenish brown hawk moth, straight burr rice hesperiidae, pelopidas mathias, Papilio xuthus, Common Mormon, cabbage butterfly, pyrameis indica, ramie, Beans blister beetle, Venus ground beetle, wrinkle sheath ground beetle, wheat head ground beetle, pleonomus canaliculatus, Agriotes subrittatus Motschulsky, khapra beetle, attagenus piceus, citrus are small Buprestid beetle, golden edge buprestid beetle, yellow meal worm, dark mealworm, red flour beetle, confused flour beetle, verdigris different beetle, H. parallela, North China Holotrichia oblita, mulberry borer, longicorn beetle, nadezhdiella cantori, pink neck longicorn, big daikon leaf beetle, daicon leaf beetle, aulacophora femoralis, yellow knee Flea beetle, Callosobruchus chinensis, pea weevil, broad bean weevil, sitophilus zea-mais, rice weevil, dolerus tritici, pear fruit sawfly, yellowish leukorrhea ichneumon wasp, armyworm white star ichneumon wasp, Corn earworm hangs cocoon ichneumon wasp, Campoletis chlorideae, snout moth's larva stain wart ichneumon wasp, mosquito, fly, horsefly, wheat midge, contarinia tritici, rice goitre Mosquito, citrus fruit fly, melonfly, the latent fly of wheat leaf ash, Americal rice leaf miner, Soybean stem borer, frit fly, Hylemyia Platura Meigen, onion fly, radish fly, Full skirt Exorista civilis, corn borer are strict to post fly, armyworm；The plant of the Pesticidal combination preventing and treating is selected from：Paddy, wheat, barley, swallow Wheat, corn, sorghum, sweet potato, potato, cassava, soybean, garden pea, broad bean, pea, mung bean, red bean, cotton, silkworm and mulberry, peanut, Rape, sesame, sunflower, beet, sugarcane, coffee, cocoa, ginseng, fritillaria, 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, apple, mandarin orange Tangerine and peach, tea, wild vegetables, bamboo shoots, hops, pepper, banana, papaya, orchid, potted landscape
Embodiment 9：The piperidines thiazole oxime ether methoxy base acrylate derivative V of the present invention is with antimicrobial combination in preventing and treating agriculture Application in industry and forestry and gardening plant disease：
All piperidines thiazole oxime ether methoxy base acrylate derivative V of the present invention and any one in commodity bactericide Or two kinds of combinations form bactericidal composition and are used to prevent and treat agricultural and forestry and gardening plant disease, the commodity bactericide choosing From：Diazosulfide, tiadinil, are abbreviated as TDL, tisocromide, first thiophene and lure amine, 4- methyl isophthalic acids, 2,3- thiadiazoles -5- formic acid, 4- methyl isophthalic acids, 2,3- thiadiazoles -5- sodium formates, 4- methyl isophthalic acids are 2,3- thiadiazoles -5- Ethyl formates, DL- beta-aminobutyric acids, different Metsulfovax, its English is general entitled：Isotianil, 3,4- dichloros and thiazole -5- formic acid, the chloroisothiazole -5- formic acid of 3,4- bis- Sodium, the chloroisothiazole -5- Ethyl formates of 3,4- bis-, virazole, antofine, Ningnanmycin or salicylic acid, cymoxanil, thiram, good fortune U.S. zinc, Mancozeb, aliette, thiophanate-methyl, Bravo, enemy can pine, procymidone, fenpropidin, thiophanate methyl, Tobes Tianjin, Metalaxyl-M, flumorph, dimethomorph, mefenoxam, benalaxyl-M, double chlorine zarilamid, flusulfamide, first flusulfamide, Thiophene fluorine bacterium amine, flutolanil, tecloftalam, ring propionyl bacterium amine, cyflufenamid, fenhexamid, zarilamid, Silthiopham, furametpyr, Pyrrole metsulfovax, mandipropamid, zoxamide, fenfuram, carboxin, chlozolinate, iprodione, Fluoxastrobin, dimoxystrobin, fluorine are phonetic Bacterium ester, kresoxim-methyl, SSF 126, orysastrobin, ZEN 90160, pyraclostrobin, trifloxystrobin, Enestroburin, alkene oxime amine, oxygen ring Azoles, bromuconazole, Cyproconazole, Difenoconazole, olefin conversion, efficient olefin conversion, epoxiconazole, RH-7592, Fluquinconazole, Flusilazole, Flutriafol, hexaconazole, glyoxalin, kind bacterium azoles, metconazole, nitrile bacterium azoles, penconazole, propiconazole, prothioconazoles, simeconazoles, penta azoles Alcohol, tetraconazole, Triadimenol, triticonazole, bitertanol, probenazole, furidazol, imazalil, efficient imazalil, Prochloraz, Fluorine bacterium azoles, cyazofamid, Fenamidone, Evil imidazoles, pefurazoate, famoxadones, the spirit of SYP-Z048, hymexazo, Evil frosts, thiazole bacterium Amine, Grandox fumigant, octhilinone, benthiozole, dodemorph, butadiene morpholine, tridemorph, fenpiclonil, fludioxonil, fluazinam, It is pyrifenox, ring pyridine bacterium amine, Boscalid, fluopicolide, pyridine bacterium amine, cyprodinil, fluorine mepanipyrim, ferimzone, mepanipyrim, phonetic Mould amine, Fenarimol, nuarimol, chinomethionat, dithianon, ethoxyquin, oxyquinoline, the third oxygen quinoline, benzene oxygen quinoline Quinoline, diethofencarb, iprovalicarb, benzene metsulfovax, Propamocarb, methasulfocarb, edifenphos, different rice blast net, pyrazophos, tolelofos-methyl, Blasticidin-S, kasugarnycin, polyoxin, Polyoxin, valida, jinggangmeisu, streptomysin, metalaxyl, furalaxyl, benzene frost Spirit, ofurace, mebenil, carbendazim, benomyl, thiophanate-methyl, triazolone, bupirimate, dimethirimol, second are phonetic Phenol, difoltan, captan, folpet, vinclozolin, fluoromide, dimethachlon, Bravo, Isoprothiolane, kitazine, leaf Withered azoles, pentachloronitrobenzene, Propineb, phosethyl-Al, sulphur, Bordeaux mixture, copper sulphate, copper oxychloride, cuprous oxide, hydrogen-oxygen Change copper, metrafenone, Pencycuron, diclomezin, Rabcide, pyroquilon, volution bacterium amine, tricyclazole, triforine, many fruit pyridines, biguanides Pungent salt, iminoctadine, botran, benzene flusulfamide, toluene flusulfamide, K-281, fenaminosulf, oxolinic acide, probenazole, bromine nitre Alcohol, iodomethane, metham-sodium, enemy's line ester, dazomet, nemamort, lythidathion, cadusafos, fensulfothion, thionazin, fenamiphos, go out Line phosphorus, dichlofenthion, isazofos, fosthietan, oxamyl, Aldicarb, carbofuran, vikane, dichloropropylene, dichloro-isonicotinic acid, Allyl isothiazole；The piperidines thiazole oxime ether methoxy base acrylate derivative V of the present invention is total in the bactericidal composition Weight/mass percentage composition is 1%-90%, and piperidines thiazole oxime ether methoxy base acrylate derivative V of the invention is killed with foregoing commodity The ratio of microbial inoculum is mass percent 1%: 99% to 99%: 1%；The formulation of the bactericidal composition processing is selected from：At seed Manage emulsion, aqueous emulsion, microemulsion, suspension emulsion, capsule suspension, water-soluble granule, granula subtilis, soluble thick agent, poison grain, bulk Poison bait, granular poison bait, sheet poison bait, dense poison bait, sustained-release block, electrostatic spray agent, oil in water emulsion, smoke candle, smoke candle, smog Cylinder, smog rod, smog piece, smog ball, foaming agent, ointment, thermal fog, harl agent, aerosol, the agent of solid-liquid mixing dress, liquid liquid Solid mixing dress agent, solid/mixing dress agent, medicine paint, fine granule, follow the trail of pulvis, oil suspending agent, oil-dispersing property pulvis, dense jelly, bold and vigorous pour Agent, seed coat agent, liniment, film forming finish, ultra low volume liquids, steam releasing agent；The phytopathy of the bactericidal composition preventing and treating Evil is selected from：Seedling blight of rice, tomato root rot, the late blight of potato, tobacco black shank, millet powdery mildew, downy mildew of garpe, lettuce Lettuce downy mildew, cucumber downy mildew, cucumber anthracnose；The applicable plant of the bactericidal composition is selected from：Paddy, wheat, barley, swallow Wheat, corn, sorghum, sweet potato, potato, cassava, soybean, garden pea, broad bean, pea, mung bean, red bean, cotton, silkworm and mulberry, peanut, Rape, sesame, sunflower, beet, sugarcane, coffee, cocoa, ginseng, fritillaria, 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, apple, mandarin orange Tangerine and peach, tea, wild vegetables, bamboo shoots, hops, pepper, banana, papaya, orchid, potted landscape.
Embodiment 10：The piperidines thiazole oxime ether methoxy base acrylate derivative V of the present invention is combined with anti-plant virus agent Application in preventing and treating agricultural and forestry and gardening plant virus disease：
The present invention all piperidines thiazole oxime ether methoxy base acrylate derivative V with it is any in commodity antiviral agent One or two combination, which forms antiviral composition, to be used to prevent and treat agricultural and forestry and gardening plant virus disease, the commodity Antiviral agent is selected from：Diazosulfide, tiadinil, are abbreviated as TDL, isotianil, and its English is general entitled： Isotianil, 4- methyl isophthalic acid, 2,3- thiadiazoles -5- formic acid, 4- methyl isophthalic acids, 2,3- thiadiazoles -5- sodium formates, 4- methyl isophthalic acids, 2, 3- thiadiazoles -5- Ethyl formates, the chloroisothiazole -5- formic acid of 3,4- bis-, the chloroisothiazole -5- sodium formates of 3,4- bis-, 3,4- dichloros are different Thiazole -5- Ethyl formates, DL- beta-aminobutyric acids, virazole, antofine, Ningnanmycin, tisocromide, first thiophene lure amine or salicylic acid, Cytosintetidemycin, dichloro-isonicotinic acid, allyl isothiazole, well ridge azanol, jinggangmeisu；The piperidines thiazole oxime ether methoxy base third of the present invention Total weight/mass percentage compositions of the olefin(e) acid ester derivant V in the antiviral composition is 1%-90%, piperidines thiophene of the invention The ratio of azoles oxime ether methoxy base acrylate derivative V and foregoing commodity anti-plant virus agent is that mass percent 1%: 99% is arrived 99%: 1%；The formulation of the antiviral composition processing is selected from：Seed treatment emulsion, aqueous emulsion, microemulsion, suspension emulsion, glue Capsule suspending agent, water-soluble granule, granula subtilis, soluble thick agent, poison grain, block poison bait, granular poison bait, sheet poison bait, dense poison bait, Sustained-release block, electrostatic spray agent, oil in water emulsion, smoke candle, smoke candle, smoke cartridge, smog rod, smog piece, smog ball, get angry Solid agent, ointment, thermal fog, harl agent, aerosol, the agent of solid-liquid mixing dress, the agent of liquid liquid mixing dress, solid/mixing fill agent, medicine paint, Fine granule, follow the trail of pulvis, oil suspending agent, oil-dispersing property pulvis, dense jelly, sprinkle pour agent, it is seed coat agent, liniment, film forming finish, ultralow Volume liquids, steam releasing agent；The virus disease of the antiviral composition preventing and treating is selected from：Rice dwarf virus disease, BYDV, striped Leaf blight, fern leaf of tomato viral disease, pepper mosaic virus disease viral disease, tobacco veinal necrosis virus disease, maize dwarf mosaic, Cauliflower Mosaic Virus, citrus virosis, cymbidium mosaic virus, cybidium ring spot virus；The plant that the antiviral composition is used to prevent and treat is selected from： It is paddy, wheat, barley, oat, corn, sorghum, sweet potato, potato, cassava, soybean, garden pea, broad bean, pea, mung bean, small Beans, cotton, silkworm and mulberry, peanut, rape, sesame, sunflower, beet, sugarcane, coffee, cocoa, ginseng, fritillaria, rubber, coconut, oil Palm fibre, sisal hemp, tobacco, tomato, capsicum, radish, cucumber, Chinese cabbage, celery, hot pickled mustard tube, beet, rape, green onion, garlic, watermelon, muskmelon, Kazakhstan Close melon, pawpaw, apple, citrus and peach, tea, wild vegetables, bamboo shoots, hops, pepper, banana, papaya, orchid, potted landscape.
Embodiment 11：The piperidines thiazole oxime ether methoxy base acrylate derivative V of the present invention is combined with acaricide in preventing and treating Application in agricultural and forestry and gardening plant mite evil：
All piperidines thiazole oxime ether methoxy base acrylate derivative V of the present invention and any one in commodity acaricide Or two kinds of combinations form miticide composition and are used to prevent and treat agricultural and forestry and gardening plant mite evil, the commodity acaricide choosing From：Azacyclotin, plictran, fenbutatin oxide, three phosphor tins, chlorfenviphos, dimethylvinphos, crotoxyphos, DDVP, heptenophos, Menite, Azodrin, 2-dichloroethylk dimethyl phosphate, chlopyrifos, Diothyl, imino-formyl chloride sulphur phosphorus, omethoate, dioxathion, Ethodan, malathion, worm mite Fear, Phosalone, phoxim, methylpyrimidine sulphur phosphorus, quinalphos, sulfotep, Hostathion, Kilval, isocarbophos, acephatemet, Propetamphos, dialifos, phosmet, acrinathrin, Biphenthrin, lambda-cyhalothrin, smart gamma cyhalothrin, first cyanogen Chrysanthemum ester, flucythrinate, flumethrin, taufluvalinate, brofluthrinate, Bifenazate, fenothiocarb, Aldicarb, butocarboxim, Oxamyl, Talcord, thiofanox, benomyl, sok, carbofuran, carbosulfan, MTMC, promacyl, Carzol, Single carbonamidine, medimeform, Amitraz, Spanon, Ergol, fenisobromolate, cyflumetofen, acequinocyl, Nissol, flufenoxuron, Macro tetrolide, piericidin, thuringiensin, tetranactin, macro tetrolide, AVM, doractin, eprinomectin, she Tie up rhzomorph, selamectin, moxidectin, pyrethrin, nicotine, matrine, nimbin, rotenone, tebufenpyrad, pyridaben, azoles Mite ester, clofentezine, propargite, Hexythiazox, Envidor, fluacrypyrim, chlorfenizon, propargite, pyridaben；The piperidines thiazole of the present invention Total weight/mass percentage compositions of the oxime ether methoxy base acrylate derivative V in the miticide composition is 1%-90%, this hair Bright piperidines thiazole oxime ether methoxy base acrylate derivative V and the acaricidal ratio of the commodity are mass percent 1%: 99% to 99%: 1%；The formulation of the miticide composition processing is selected from：Seed treatment emulsion, aqueous emulsion, microemulsion, outstanding breast It is agent, capsule suspension, water-soluble granule, granula subtilis, soluble thick agent, poison grain, block poison bait, granular poison bait, sheet poison bait, dense Poison bait, sustained-release block, electrostatic spray agent, oil in water emulsion, smoke candle, smoke candle, smoke cartridge, smog rod, smog piece, smog ball, Gu foaming agent, ointment, thermal fog, harl agent, aerosol, the agent of solid-liquid mixing dress, the agent of liquid liquid mixing dress, solid/mixing dress agent, medicine Paint, fine granule, follow the trail of pulvis, oil suspending agent, oil-dispersing property pulvis, dense jelly, sprinkle pour agent, seed coat agent, liniment, film forming finish, Ultra low volume liquids, steam releasing agent；The mite evil of the miticide composition preventing and treating is selected from：Mite evil selected from Tetranychidae, Tenuipalpidae, Furan line mite, Eriophyidae, tetranychus telarius category, the evil mite of Eriophyidae, these evil mites are worldwide Agricultural Mites, forestry harmful mites, gardening evil Mite and hygienic evil mite；The plant that the miticide composition is used to prevent and treat is selected from：Paddy, wheat, barley, oat, corn, sorghum, Sweet potato, potato, cassava, soybean, garden pea, broad bean, pea, mung bean, red bean, cotton, silkworm and mulberry, peanut, rape, sesame, to Day certain herbaceous plants with big flowers, beet, sugarcane, coffee, cocoa, ginseng, fritillaria, rubber, coconut, oil palm, sisal hemp, tobacco, tomato, capsicum, radish, Huang Melon, Chinese cabbage, celery, hot pickled mustard tube, beet, rape, green onion, garlic, watermelon, muskmelon, "Hami" melon, pawpaw, apple, citrus and peach, tea, Wild vegetables, bamboo shoots, hops, pepper, banana, papaya, orchid, potted landscape.
The piperidines thiazole oxime ether methoxy base acrylate derivative V of the present invention of table 2 bacteriostatic activity be (50 mcg/mls Inhibiting rate/%)
Sequence number Compound AS CA GZ PP BC SS RC PS PI
1 CL04-43A 41.82 54.17 51.52 52.94 75.00 52.94 78.00 54.55 62.86
2 CL04-43B 45.45 54.17 39.39 52.94 73.21 41.18 78.00 42.42 54.29
3 CL04-45A 9.09 12.50 21.21 36.13 55.36 52.94 50.00 30.30 17.14
4 CL04-45B 27.27 33.33 57.58 36.13 46.43 64.71 74.00 45.45 45.71
5 CL04-45C 27.27 33.33 51.52 56.30 42.86 29.41 68.00 30.30 28.57
6 CL04-45D 41.82 58.33 48.48 52.10 76.79 64.71 70.00 54.55 54.29
7 CL04-45E 5.45 12.50 21.21 21.01 41.07 5.88 38.00 15.15 17.14
8 CL04-45F 12.73 16.67 27.27 24.37 25.00 64.71 46.00 24.24 14.29
9 CL05-15 41.82 54.17 51.52 52.94 75.00 52.94 78.00 54.55 62.85
10 CL05-00 21.56 13.42 20.11 20.43 30.87 30.10 15.08 20.76 21.61
11 Fluoxastrobin 75.00 55.56 71.43 100 91.18 88.10 84.06 80.77 46.88
The piperidines thiazole oxime ether methoxy base acrylate derivative V of the present invention of table 3 bacteriostatic activity (inhibiting rate/%)
The piperidines thiazole oxime ether methoxy base acrylate derivative V of the present invention of table 4 activity of resisting tobacco mosaic virus (100 Inhibiting rate/% of mcg/ml)
Sequence number Compound Therapeutic mode Passivation pattern Protected mode Induction pattern
1 CL04-43A 1.52±0.62 25.24±6.60 40.21±1.21 50.81±0.21
2 CL04-43B 85.00±3.55 0.89±0.21 53.79±2.83 63.79±8.83
3 CL04-45A 49.98±0.49 0.44±0.11 34.92±3.17 44.92±4.17
4 CL04-45B 1.52±0.62 0.44±0.21 39.64±0.87 39.64±0.87
5 CL04-45C 29.52±3.92 4.60±0.99 44.89±0.46 74.89±7.46
6 CL04-45D 70.76±2.70 2.22±0.85 46.30±1.16 66.30±2.16
7 CL04-45E 42.79±0.93 2.22±0.85 36.47±0.08 56.47±3.08
8 CL04-45F 62.91±2.62 41.79±0.92 32.53±1.50 52.53±6.70
9 CL05-15 34.92±1.17 23.10±1.04 30.21±1.62 30.20±1.24
10 CL05-00 30.32±1.12 11.42±1.10 23.43±1.50 12.44±2.16
11 Ningnanmycin 74.10±2.04 - - -
12 TDL - - - 65.00±2.00
13 BTH - - 78.10±0.54 78.00±1.34
14 SZG-7 - - - 79.00±2.27
15 Virazole - 78.00±1.00 - -

Claims (9)

1. a class piperidines thiazole oxime ether methoxy base acrylate derivative, it is characterised in that lead to the chemical constitution shown in Formula V Formula：
Wherein, R1It is selected from：Methyl, hydrogen；R2It is selected from：1,2- bis- fluoro ethyl, propargyl, cyclopropyl, methyl, 1- methyl mercapto -2- methyl Propyl- 2- bases, (R) -1- methyl mercapto propyl- 2- bases；R3It is selected from：Hydrogen, hydrogen chloride；X is selected from：Oxygen, nitrogen, n=1,2.
2. the synthetic method of the piperidines thiazole oxime ether methoxy base acrylate derivative V described in claim 1, specific synthetic route For：
Wherein, R1It is selected from：Methyl, hydrogen；R2It is selected from：1,2- bis- fluoro ethyl, propargyl, cyclopropyl, methyl, 1- methyl mercapto -2- methyl Propyl- 2- bases, (R) -1- methyl mercapto propyl- 2- bases；R3It is selected from：Hydrogen, hydrogen chloride；X is selected from：Oxygen, nitrogen, n=1,2；
The synthetic method of piperidines thiazole oxime ether methoxy base acrylate derivative described in claim 1 is divided into following steps：
A. compound II preparation：
1.10 mMs of compound I are added in 25 milliliters of single necked round bottom flask, are dissolved with 15 milliliters of ethanol, 1.00 millis are added Mole substituted piperidine thiazole carbonyls, the piperidines thiazole carbonyls is selected from：Piperidines thiazolone, piperidines thiazole aldehyde, Two hydrochloric acid for dripping 2 mol/Ls are added dropwise in most backward reaction system, are stirred at room temperature 12 hours, removal of solvent under reduced pressure after reaction completely, Residue purifies to obtain compound II through 200~300 mesh silica gel column chromatographies, and eluant, eluent is 60~90 degrees Celsius of petroleum ether: acetic acid Ethyl ester, according to the difference of product, volume ratio is 9: 1-2: 1, yield 40-50%；Amount and reaction vessel prepared by compound II Volume is expanded or shunk by corresponding proportion；
B. compound III preparation：
0.24 mM of compound II is added in 25 milliliters of single necked round bottom flask, is dissolved with 15 ml methanols, is added into reaction Enter mM sodium hydroxide of 0.03 gram, i.e., 0.72, be then heated to reflux 30 minutes, reaction concentrates reaction solution after terminating, it is remaining Thing is diluted with 10 milliliters of ethyl acetate, and the water for adding 10 milliliters all dissolves solid, separates water-yielding stratum, 2 mol/Ls of water layer Salt acid for adjusting pH to 3, be then extracted with ethyl acetate, aqueous layer with ethyl acetate be stripped one time, merge organic layer, organic layer use Saturated sodium-chloride is washed one time, anhydrous sodium sulfate drying, suction filtration, and removal of solvent under reduced pressure obtains compound III；Yield 95-100%；Change Amount and the volume of reaction vessel prepared by compound III is expanded or shunk by corresponding proportion；
C. compound IV preparation：
0.30 mM of compound III is added in 25 milliliters of single necked round bottom flask, is dissolved with 15 milliliters of dry dichloromethane, The EDCI of 0.69 gram, i.e., 0.36 mM, i.e. 1- ethyls-(3- dimethylaminopropyls) carbodiimide hydrochloride are added into reaction The HOBT of salt and 0.43 gram, i.e., 0.32 mM, i.e. 1- hydroxy benzo triazoles, are stirred at room temperature 30 minutes after adding, then The R of 0.32 mM of addition into reaction system2-XHn, n=1,2；It is stirred at room temperature 2 hours, after reaction terminates, reaction solution uses 15 Twice of the washing of milliliter, isolates organic layer, organic layer is respectively washed one time with saturated sodium bicarbonate and saturated sodium-chloride respectively, anhydrous Sodium sulphate is dried, suction filtration, removal of solvent under reduced pressure, and residue obtains white solid through the purifying of 200~300 mesh silica gel column chromatographies, washes De- agent is 60~90 degrees Celsius of petroleum ether: ethyl acetate, and volume ratio is 4: 1, yield 60%-95%；Prepared by compound IV Amount and the volume of reaction vessel are expanded or shunk by corresponding proportion；
D. compound V preparation：
0.30 mM of compound IV, with 15 milliliters of dry dichloromethane, ice are added in 25 milliliters of single necked round bottom flask The trifluoroacetic acid of 1.5 milliliters of drop under the conditions of bath, addition is finished, is stirred overnight at room temperature, and reaction terminates, with 1 mole every liter of hydrogen-oxygen Change sodium and be neutralized to pH=7-8, isolate organic layer, organic layer is respectively washed one time with saturated sodium bicarbonate and saturated sodium-chloride respectively, Anhydrous sodium sulfate drying, suction filtration, removal of solvent under reduced pressure, it is solid that residue obtains white through the purifying of 200~300 mesh silica gel column chromatographies Body, eluant, eluent is dichloromethane: methanol, and volume ratio is 8: 1, yield 96.26%；Amount and reaction vessel prepared by compound V Volume is expanded or shunk by corresponding proportion.
3. the piperidines thiazole oxime ether methoxy base acrylate derivative V described in claim 1 exists with agriculturally acceptable auxiliary agent Prepare the purposes in bactericide.
4. the piperidines thiazole oxime ether methoxy base acrylate derivative V described in claim 1 exists with agriculturally acceptable auxiliary agent Prepare the purposes in resisting tobacco mosaic virus agent.
5. the piperidines thiazole oxime ether methoxy base acrylate derivative V described in claim 1 exists with agriculturally acceptable auxiliary agent Prepare the purposes that activating plants agent is used in evoking tobacco resisting tobacco mosaic virus.
6. the piperidines thiazole oxime ether methoxy base acrylate derivative V described in claim 1 is with insecticide composition in preventing and treating agricultural With the purposes in forestry and gardening plant insect pest：
Piperidines thiazole oxime ether methoxy base acrylate derivative V described in claim 1 and any one in commodity insecticide Or two kinds of combinations form Pesticidal combination and are used to prevent and treat agricultural and forestry and gardening plant insect pest, the commodity insecticide choosing From：Chlopyrifos, Asia Nong, Acetamiprid, emamectin benzoate, milbemectin, AVM, pleocidin, fenvalerate, height Imitate fenvalerate, cypermethrin, effective cypermethrin, Cyhalothrin, decis, Fenpropathrin, Beta- cyfluthrin chrysanthemums Ester, Lambda- Cyhalothrins, Permanone, permethrin, allethrin, Biphenthrin, Permethrin, ethofenprox, Flumethrin, fluvalinate, imidacloprid, Nitenpyram, imidaclothiz, thiacloprid, Diacloden, clothianidin, MTI-446, Clothianadin, Da Tenan, diflubenzuron, d ichlorbenzuron, Teflubenzuron, grand deinsectization, HEXAFLUMURON, flufenoxuron, grand pyridine worm, lufenuron, poisonous insect urea, Penfluron, Noviflumuron are noviflumuron, its No. CAS be 121451-02-3, flucycloxuron, Novaluron be Rimon, Chlorfluazuron, Bay sir 6874 are 1- [(3.5- bis- chloro- 4) 4-nitrophenoxy phenyl 3-3- (2- chlorobenzenes)-urea, Bay SIR- 8514 i.e. 1- (4- Trifluoromethoxyphen-ls) -3- (2- chlorobenzenes)-urea, piperazine worm urea, Bistrifluron is bistrifluron, furans Tebufenozide, tebufenozide, chlorine tebufenozide, methoxyfenozide, ring tebufenozide, Rogor, flolimat, DDVP, orthene, three Azoles phosphorus, quinalphos, pyridaphethione, isazofos, isoprocarb, sevin, Aphox, MTMC, Mobucin, cartap, Bassa, Leaf disperses, carbaryl, Benfuracard micro, carbosulfan, cartap, fenisobromolate, Hexythiazox, fenpyroximate, pyridaben, four mites Piperazine, propargite, diafenthiuron, pymetrozine, Envidor, spiral shell worm ester, spiral shell worm ethyl ester, butene-fipronil, azacyclotin, Buprofezin, go out line Phosphorus, ethiprole, Cupric sulfate, dimehypo, chlorantraniliprole, Flubendiamide, fluorine cyanogen insect amide, cyanogen insect amide, Tolfenpyrad, bromine worm Nitrile, pyrazinones, etoxazole, tebufenpyrad, rattle away young ketone, Nylar, emaricin；Piperidines thiazole oxime ether first described in claim 1 Weight/mass percentage compositions of the epoxide acrylate derivative V in the Pesticidal combination is 1%-90%, described in claim 1 The ratio of piperidines thiazole oxime ether methoxy base acrylate derivative V and foregoing commodity insecticide is that mass percent 1%: 99% is arrived 99%: 1%；The formulation of the Pesticidal combination processing is selected from：Seed treatment emulsion, aqueous emulsion, microemulsion, suspension emulsion, capsule It is suspending agent, water-soluble granule, granula subtilis, soluble thick agent, poison grain, block poison bait, granular poison bait, sheet poison bait, dense poison bait, slow Release block, electrostatic spray agent, oil in water emulsion, smoke candle, smoke candle, smoke cartridge, smog rod, smog piece, smog ball, foaming agent, Gu ointment, thermal fog, harl agent, aerosol, the agent of solid-liquid mixing dress, the agent of liquid liquid mixing dress, solid/mixing dress agent, medicine paint, particulate Agent, follow the trail of pulvis, oil suspending agent, oil-dispersing property pulvis, dense jelly, sprinkle pour agent, seed coat agent, liniment, film forming finish, ultra-low volume Liquor, steam releasing agent；The insect pest of the plant of the Pesticidal combination preventing and treating is selected from：Red spider, Asiatic migrotory locust, reading room management, in Magnificent oryza chinensis, Patanga japonica (l.Bol.), single thorn mole cricket, Oriental burmeister, rice thripses, onion thrips, greenhouse thrips, haplothrips aculeatus, Mai Jian pipe Jis Horse, Trialeurodes vaporariorum Westwood, Bemisia tabaci, rice green leafhopper, green leaf hopper, chlorita biguttula, spot clothing plant hopper, brown paddy plant hopper, white backed planthopper, ash fly The sharp shield of the flat angle plant hopper of lice, sugarcane, cotten aphid, green bugs, grain aphid, black peach aphid, kaoliang aphid, radish aphid, icerya purchasi, Pseudaulacaspis pentagona, arrow A red-spotted lizard, san jose scale, wax insect, ceroplastes rubens, Didesmococcus koreanus Borchs, pear lace bug, banana lace bug, thin corner piece stinkbug, Orius minutus, slender rice bug, Paddy fly, niphe elongata, scotinophora lurida, green rice bug, green plant bug, alfalfa plant bug, black striped plant bug, chrysopa septempunctata, beautiful Chrysopa, China's grass It is sandfly, rain moth, casemaking clothes moth, oriental moth, brown slug moth, flat perverse moth, gelechiid, pink bollworm, brachmia triannuella, diamondback moth, small heart-eating peach worm, big Beans heart-eating worm, small heart-eating peach worm, apple Spilonota lechriaspis, brown belt length leaf roller, Adoxophyes cyrtosema, striped rice borer, bean-pod borer, jade Rice snout moth's larva, yellow rice borer, Oeobia undalis, rice leaf roller, bar snout moth's larva, Notarchaderogata, dichocrocis punctiferalis, armyworm, prodenia litura, rice green caterpillar, cotton are small Bridging worm, beet armyworm, pink rice borer, bollworm, ancient cooking vessel point spark, black cutworm, big cutworm, yellow cutworm, robber poison moth, dance poison Moth, palaearctic sweet potato, greenish brown hawk moth, straight burr rice hesperiidae, pelopidas mathias, Papilio xuthus, Common Mormon, cabbage butterfly, pyrameis indica, It is a ramie Huang a kind of butterfly harmful to crop plants, beans blister beetle, Venus ground beetle, wrinkle sheath ground beetle, wheat head ground beetle, pleonomus canaliculatus, Agriotes subrittatus Motschulsky, khapra beetle, black It is the small buprestid beetle of khapra beetle, citrus, golden edge buprestid beetle, yellow meal worm, dark mealworm, red flour beetle, confused flour beetle, verdigris different beetle, dark Dark fund tortoise, holotrichia oblita, mulberry borer, longicorn beetle, nadezhdiella cantori, pink neck longicorn, big daikon leaf beetle, daicon leaf beetle, Huang It is cucumber beetle, phyllotreta striolata, Callosobruchus chinensis, pea weevil, broad bean weevil, sitophilus zea-mais, rice weevil, dolerus tritici, pear fruit sawfly, yellowish leukorrhea ichneumon wasp, glutinous It is yellow that worm white star ichneumon wasp, corn earworm hang cocoon ichneumon wasp, Campoletis chlorideae, snout moth's larva stain wart ichneumon wasp, mosquito, fly, horsefly, wheat midge, wheat Suction pulp worm, pachydiplosis oryzae, citrus fruit fly, melonfly, the latent fly of wheat leaf ash, Americal rice leaf miner, Soybean stem borer, frit fly, Hylemyia Platura Meigen, Onion fly, radish fly, full skirt Exorista civilis, corn borer are strict to post fly, armyworm；The plant of the Pesticidal combination preventing and treating is selected from：It is paddy, small Wheat, barley, oat, corn, sorghum, sweet potato, potato, cassava, soybean, garden pea, broad bean, pea, mung bean, red bean, cotton, Silkworm and mulberry, peanut, rape, sesame, sunflower, beet, sugarcane, coffee, cocoa, ginseng, fritillaria, 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, wood Melon, apple, citrus and peach, tea, wild vegetables, bamboo shoots, hops, pepper, banana, papaya, orchid, potted landscape.
7. the piperidines thiazole oxime ether methoxy base acrylate derivative V described in claim 1 is with antimicrobial combination in preventing and treating agricultural With the purposes in forestry and gardening plant disease：
Piperidines thiazole oxime ether methoxy base acrylate derivative V described in claim 1 and any one in commodity bactericide Or two kinds of combinations form bactericidal composition and are used to prevent and treat agricultural and forestry and gardening plant disease, the commodity bactericide choosing From：Diazosulfide, tiadinil, are abbreviated as TDL, tisocromide, first thiophene and lure amine, 4- methyl isophthalic acids, 2,3- thiadiazoles -5- formic acid, 4- methyl isophthalic acids, 2,3- thiadiazoles -5- sodium formates, 4- methyl isophthalic acids are 2,3- thiadiazoles -5- Ethyl formates, DL- beta-aminobutyric acids, different Metsulfovax, its English is general entitled：Isotianil, the chloroisothiazole -5- formic acid of 3,4- bis-, the chloroisothiazole -5- formic acid of 3,4- bis- Sodium, the chloroisothiazole -5- Ethyl formates of 3,4- bis-, virazole, antofine, Ningnanmycin or salicylic acid, cymoxanil, thiram, good fortune U.S. zinc, Mancozeb, aliette, thiophanate-methyl, Bravo, enemy can pine, procymidone, fenpropidin, thiophanate methyl, Tobes Tianjin, Metalaxyl-M, flumorph, dimethomorph, mefenoxam, benalaxyl-M, double chlorine zarilamid, flusulfamide, first flusulfamide, Thiophene fluorine bacterium amine, flutolanil, tecloftalam, ring propionyl bacterium amine, cyflufenamid, fenhexamid, zarilamid, Silthiopham, furametpyr, Pyrrole metsulfovax, mandipropamid, zoxamide, fenfuram, carboxin, chlozolinate, iprodione, Fluoxastrobin, dimoxystrobin, fluorine are phonetic Bacterium ester, kresoxim-methyl, SSF 126, orysastrobin, ZEN 90160, pyraclostrobin, trifloxystrobin, Enestroburin, alkene oxime amine, oxygen ring Azoles, bromuconazole, Cyproconazole, Difenoconazole, olefin conversion, efficient olefin conversion, epoxiconazole, RH-7592, Fluquinconazole, Flusilazole, Flutriafol, hexaconazole, glyoxalin, kind bacterium azoles, metconazole, nitrile bacterium azoles, penconazole, propiconazole, prothioconazoles, simeconazoles, penta azoles Alcohol, tetraconazole, Triadimenol, triticonazole, bitertanol, probenazole, furidazol, imazalil, efficient imazalil, Prochloraz, Fluorine bacterium azoles, cyazofamid, Fenamidone, Evil imidazoles, pefurazoate, famoxadones, the spirit of SYP-Z048, hymexazo, Evil frosts, thiazole bacterium Amine, Grandox fumigant, octhilinone, benthiozole, dodemorph, butadiene morpholine, tridemorph, fenpiclonil, fludioxonil, fluazinam, It is pyrifenox, ring pyridine bacterium amine, Boscalid, fluopicolide, pyridine bacterium amine, cyprodinil, fluorine mepanipyrim, ferimzone, mepanipyrim, phonetic Mould amine, Fenarimol, nuarimol, chinomethionat, dithianon, ethoxyquin, oxyquinoline, the third oxygen quinoline, benzene oxygen quinoline Quinoline, diethofencarb, iprovalicarb, benzene metsulfovax, Propamocarb, methasulfocarb, edifenphos, different rice blast net, pyrazophos, tolelofos-methyl, Blasticidin-S, kasugarnycin, polyoxin, Polyoxin, valida, jinggangmeisu, streptomysin, metalaxyl, furalaxyl, benzene frost Spirit, ofurace, mebenil, carbendazim, benomyl, thiophanate-methyl, triazolone, bupirimate, dimethirimol, second are phonetic Phenol, difoltan, captan, folpet, vinclozolin, fluoromide, dimethachlon, Bravo, Isoprothiolane, kitazine, leaf Withered azoles, pentachloronitrobenzene, Propineb, phosethyl-Al, sulphur, Bordeaux mixture, copper sulphate, copper oxychloride, cuprous oxide, hydrogen-oxygen Change copper, metrafenone, Pencycuron, diclomezin, Rabcide, pyroquilon, volution bacterium amine, tricyclazole, triforine, many fruit pyridines, biguanides Pungent salt, iminoctadine, botran, benzene flusulfamide, toluene flusulfamide, K-281, fenaminosulf, oxolinic acide, probenazole, bromine nitre Alcohol, iodomethane, metham-sodium, enemy's line ester, dazomet, nemamort, lythidathion, cadusafos, fensulfothion, thionazin, fenamiphos, go out Line phosphorus, dichlofenthion, isazofos, fosthietan, oxamyl, Aldicarb, carbofuran, vikane, dichloropropylene, dichloro-isonicotinic acid, Allyl isothiazole；Piperidines thiazole oxime ether methoxy base acrylate derivative V described in claim 1 is in the bactericidal composition Total weight/mass percentage composition be 1%-90%, the piperidines thiazole oxime ether methoxy base acrylate derivative V described in claim 1 Ratio with foregoing commodity bactericide is mass percent 1%: 99% to 99%: 1%；The formulation of the bactericidal composition processing It is selected from：Seed treatment emulsion, aqueous emulsion, microemulsion, suspension emulsion, capsule suspension, water-soluble granule, granula subtilis, soluble thick Agent, poison grain, block poison bait, granular poison bait, sheet poison bait, dense poison bait, sustained-release block, electrostatic spray agent, oil in water emulsion, smog Tank, smoke candle, smoke cartridge, smog rod, smog piece, smog ball, foaming agent, ointment, thermal fog, harl agent, aerosol, solid-liquid Gu the agent of mixing dress, liquid liquid mix dress agent, solid/mixing dress agent, medicine paint, fine granule, tracking pulvis, oil suspending agent, oil-dispersing property powder Agent, dense jelly, sprinkle pour agent, seed coat agent, liniment, film forming finish, ultra low volume liquids, steam releasing agent；The Bactericidal composite The plant disease of thing preventing and treating is selected from：Seedling blight of rice, tomato root rot, the late blight of potato, tobacco black shank, millet white powder Disease, downy mildew of garpe, downy mildew of lettuce, cucumber downy mildew, cucumber anthracnose；The applicable plant of the bactericidal composition is selected from： It is paddy, wheat, barley, oat, corn, sorghum, sweet potato, potato, cassava, soybean, garden pea, broad bean, pea, mung bean, small Beans, cotton, silkworm and mulberry, peanut, rape, sesame, sunflower, beet, sugarcane, coffee, cocoa, ginseng, fritillaria, rubber, coconut, oil Palm fibre, sisal hemp, tobacco, tomato, capsicum, radish, cucumber, Chinese cabbage, celery, hot pickled mustard tube, beet, rape, green onion, garlic, watermelon, muskmelon, Kazakhstan Close melon, pawpaw, apple, citrus and peach, tea, wild vegetables, bamboo shoots, hops, pepper, banana, papaya, orchid, potted landscape.
8. the piperidines thiazole oxime ether methoxy base acrylate derivative V described in claim 1 combines preventing and treating with anti-plant virus agent Purposes in agricultural and forestry and gardening plant virus disease：
Piperidines thiazole oxime ether methoxy base acrylate derivative V described in claim 1 with it is any in commodity antiviral agent One or two combination, which forms antiviral composition, to be used to prevent and treat agricultural and forestry and gardening plant virus disease, the commodity Antiviral agent is selected from：Diazosulfide, tiadinil, are abbreviated as TDL, isotianil, and its English is general entitled： Isotianil, 4- methyl isophthalic acid, 2,3- thiadiazoles -5- formic acid, 4- methyl isophthalic acids, 2,3- thiadiazoles -5- sodium formates, 4- methyl isophthalic acids, 2, 3- thiadiazoles -5- Ethyl formates, the chloroisothiazole -5- formic acid of 3,4- bis-, the chloroisothiazole -5- sodium formates of 3,4- bis-, 3,4- dichloros are different Thiazole -5- Ethyl formates, DL- beta-aminobutyric acids, virazole, antofine, Ningnanmycin, tisocromide, first thiophene lure amine or salicylic acid, Cytosintetidemycin, dichloro-isonicotinic acid, allyl isothiazole, well ridge azanol, jinggangmeisu；Piperidines thiazole oxime ether described in claim 1 Total weight/mass percentage compositions of the methoxy acrylate derivative V in the antiviral composition is 1%-90%, and right will The ratio for asking the piperidines thiazole oxime ether methoxy base acrylate derivative V described in 1 and foregoing commodity anti-plant virus agent is quality Percentage 1%: 99% to 99%: 1%；The formulation of the antiviral composition processing is selected from：Seed treatment emulsion, aqueous emulsion, Microemulsion, suspension emulsion, capsule suspension, water-soluble granule, granula subtilis, soluble thick agent, poison grain, block poison bait, granular poison bait, Sheet poison bait, dense poison bait, sustained-release block, electrostatic spray agent, oil in water emulsion, smoke candle, smoke candle, smoke cartridge, smog rod, smog Gu piece, smog ball, foaming agent, ointment, thermal fog, harl agent, aerosol, the agent of solid-liquid mixing dress, the agent of liquid liquid mixing dress, it is solid/ Mixing dress agent, medicine paint, fine granule, follow the trail of pulvis, oil suspending agent, oil-dispersing property pulvis, dense jelly, sprinkle pour agent, seed coat agent, smearing Agent, film forming finish, ultra low volume liquids, steam releasing agent；The virus disease of the antiviral composition preventing and treating is selected from：Paddy rice is short Contracting disease, BYDV, stripe virus disease, fern leaf of tomato viral disease, pepper mosaic virus disease viral disease, tobacco veinal necrosis virus disease, corn are short Mosaic disease, cauliflower mosaic virus, citrus virosis, cymbidium mosaic virus, cybidium ring spot virus；The antiviral composition is used It is selected from the plant of preventing and treating：Paddy, wheat, barley, oat, corn, sorghum, sweet potato, potato, cassava, soybean, garden pea, Broad bean, pea, mung bean, red bean, cotton, silkworm and mulberry, peanut, rape, sesame, sunflower, beet, sugarcane, coffee, cocoa, ginseng, Fritillaria, 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, apple, citrus and peach, tea, wild vegetables, bamboo shoots, hops, pepper, banana, kind Pawpaw, orchid, potted landscape.
9. the piperidines thiazole oxime ether methoxy base acrylate derivative V described in claim 1 is combined with acaricide in preventing and treating agricultural With the application in forestry and gardening plant mite evil：
Piperidines thiazole oxime ether methoxy base acrylate derivative V described in claim 1 and any one in commodity acaricide Or two kinds of combinations form miticide composition and are used to prevent and treat agricultural and forestry and gardening plant mite evil, the commodity acaricide choosing From：Azacyclotin, plictran, fenbutatin oxide, three phosphor tins, chlorfenviphos, dimethylvinphos, crotoxyphos, DDVP, heptenophos, Menite, Azodrin, 2-dichloroethylk dimethyl phosphate, chlopyrifos, Diothyl, imino-formyl chloride sulphur phosphorus, omethoate, dioxathion, Ethodan, malathion, worm mite Fear, Phosalone, phoxim, methylpyrimidine sulphur phosphorus, quinalphos, sulfotep, Hostathion, Kilval, isocarbophos, acephatemet, Propetamphos, dialifos, phosmet, acrinathrin, Biphenthrin, lambda-cyhalothrin, smart gamma cyhalothrin, first cyanogen Chrysanthemum ester, flucythrinate, flumethrin, taufluvalinate, brofluthrinate, Bifenazate, fenothiocarb, Aldicarb, butocarboxim, Oxamyl, Talcord, thiofanox, benomyl, sok, carbofuran, carbosulfan, MTMC, promacyl, Carzol, Single carbonamidine, medimeform, Amitraz, Spanon, Ergol, fenisobromolate, cyflumetofen, acequinocyl, Nissol, flufenoxuron, Macro tetrolide, piericidin, thuringiensin, tetranactin, macro tetrolide, AVM, doractin, eprinomectin, she Tie up rhzomorph, selamectin, moxidectin, pyrethrin, nicotine, matrine, nimbin, rotenone, tebufenpyrad, pyridaben, azoles Mite ester, clofentezine, propargite, Hexythiazox, Envidor, fluacrypyrim, chlorfenizon, propargite, pyridaben；Described in claim 1 Total weight/mass percentage compositions of the piperidines thiazole oxime ether methoxy base acrylate derivative V in the miticide composition is 1%- 90%, piperidines thiazole oxime ether methoxy base acrylate derivative V and the acaricidal ratio of the commodity described in claim 1 are Mass percent 1%: 99% to 99%: 1%；The formulation of the miticide composition processing is selected from：Seed treatment emulsion, water and milk Agent, microemulsion, suspension emulsion, capsule suspension, water-soluble granule, granula subtilis, soluble thick agent, poison grain, block poison bait, granular poison Bait, sheet poison bait, dense poison bait, sustained-release block, electrostatic spray agent, oil in water emulsion, smoke candle, smoke candle, smoke cartridge, smog rod, Smog piece, smog ball, foaming agent, ointment, thermal fog, harl agent, aerosol, solid-liquid mixing dress agent, liquid liquid mixing dress agent, Gu Gu/mixing dress agent, medicine paint, fine granule, follow the trail of pulvis, oil suspending agent, oil-dispersing property pulvis, dense jelly, sprinkle pour agent, seed coat agent, Liniment, film forming finish, ultra low volume liquids, steam releasing agent；The mite evil of the miticide composition preventing and treating is selected from：Mite evil is selected from Tetranychidae, Tenuipalpidae, furan line mite, Eriophyidae, tetranychus telarius category, the evil mite of Eriophyidae, these evil mites be worldwide Agricultural Mites, Forestry harmful mites, gardening evil mite and hygienic evil mite；The plant that the miticide composition is used to prevent and treat is selected from：Paddy, wheat, barley, Oat, corn, sorghum, sweet potato, potato, cassava, soybean, garden pea, broad bean, pea, mung bean, red bean, cotton, silkworm and mulberry, flower Life, rape, sesame, sunflower, beet, sugarcane, coffee, cocoa, ginseng, fritillaria, rubber, coconut, oil palm, sisal hemp, tobacco, kind Eggplant, capsicum, radish, cucumber, Chinese cabbage, celery, hot pickled mustard tube, beet, rape, green onion, garlic, watermelon, muskmelon, "Hami" melon, pawpaw, apple, Citrus and peach, tea, wild vegetables, bamboo shoots, hops, pepper, banana, papaya, orchid, potted landscape.
CN201610186472.XA 2016-03-25 2016-03-25 One class piperidines thiazole oxime ether methoxy base acrylate derivative and its production and use Pending CN107226812A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109970651A (en) * 2019-05-17 2019-07-05 南开大学 Pyrazole phenyl ethers methoxy acrylate derivative and its preparation method and application
CN110343062A (en) * 2019-08-26 2019-10-18 贵州大学 Indole derivatives, preparation method and the application of the unit containing dithioacetals
CN112592338A (en) * 2021-01-05 2021-04-02 南开大学 3, 4-dichloroisothiazole coumarin methoxyl acrylate derivatives, and preparation method and application thereof

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CN1306506A (en) * 1998-07-16 2001-08-01 诺瓦提斯公司 Phenyl-methoxyimino-acetic acid derivatives as pesticides
CN104650059A (en) * 2014-12-17 2015-05-27 南开大学 Thiazolone oxime ether derivatives, and preparation method and use thereof

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CN1306506A (en) * 1998-07-16 2001-08-01 诺瓦提斯公司 Phenyl-methoxyimino-acetic acid derivatives as pesticides
CN104650059A (en) * 2014-12-17 2015-05-27 南开大学 Thiazolone oxime ether derivatives, and preparation method and use thereof

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109970651A (en) * 2019-05-17 2019-07-05 南开大学 Pyrazole phenyl ethers methoxy acrylate derivative and its preparation method and application
CN110343062A (en) * 2019-08-26 2019-10-18 贵州大学 Indole derivatives, preparation method and the application of the unit containing dithioacetals
CN112592338A (en) * 2021-01-05 2021-04-02 南开大学 3, 4-dichloroisothiazole coumarin methoxyl acrylate derivatives, and preparation method and application thereof

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