CN104082294B - 3-aryl-5-methylbutyrolactone compound is used as the method for anti-plant virus agent - Google Patents
3-aryl-5-methylbutyrolactone compound is used as the method for anti-plant virus agent Download PDFInfo
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Abstract
3-aryl-5-methylbutyrolactone compound of the present invention is used as the method for anti-plant virus agent, relate to the anti-plant virus agent of chemical compound, comprise the method for the method for activity of resisting tobacco mosaic virus, the method in vitro Fungicidally active and live body Fungicidally active; I in 3-aryl-5-methylbutyrolactone compound
a-1 ~ I
a-9 and I
b-1 ~ I
b-9 in the concentration of 500 μ g/mL to the inhibiting rate of tobacco mosaic virus up to more than 60%, higher bactericidal activity is shown to 14 kinds of fungies.Relative to prior art, the inventive method has significant progressive and very outstanding economic benefit.
Description
Technical field
Technical scheme of the present invention relates to the anti-plant virus agent of chemical compound, and specifically 3-aryl-5-methylbutyrolactone compound is used as the method for anti-plant virus agent.
Background technology
The skeleton structure of butyrolactone is extensively present in natural products and drug molecule.3-(4-aminomethyl phenyl)-5-ethyl-DHF-2-ketone (Incrustoporin) is separated the earliest and obtains (Zapf, S. from trees basidiomycetes Incrustoporiacarneola9170; AnkeT.; Sterner, O.Acta.chem.scand.1995,49,233 – 234.), bioactivity research finds that there is certain bacteriostatic activity and cytotoxicity.The in vitro test pattern of agar diffusion method is adopted to assess its bactericidal activity, tested object is: Absidiaglauca (+) (Absidia glauca Hagem), Absidiaglauca (–), Aspergillusochraceus (Aspergillus ochraceus), Cladosporiumcladosporioides (melanomyces), Curvularialunata (Curvularia lunata), Fusariumoxysporum (Fusarium oxysporum), Fusariumfujikuroi (Fusariumsp), Mucormiehei (rice black wool is mould), Nematosporacoryli (hazel pin spore yeast), Paecilomycesvariotii (paecilomyces varioti), Penicilliumislandicum (Penicillium islandicum), Penicilliumnotatum (some mould), Ustilagonuda (smut), but to Acinetobactercalcoaceticus (Acinetobacter calcoaceticus), Arthrobactercitreus (lemon yellow arthrobacterium), Bacillusbrevis (bacillus brevis), Bacillussubtilis (bacillus subtilis), EscherichiacoliK12 (Escherichia coli), Micrococcusluteus (micrococcus luteus), the bacterial classifications such as SalmonellatyphimuriumTA98 (salmonella typhimurium) and Streptomycesspec.ATCC23836 (streptomycete) do not have inhibition.The people such as Pour successively report 3-aryl-5-alkyl-DHF-2-ketone (as the general formula I bactericidal activity to human pathogen a) (Pour, M.; Etal.Bioorg.Med.Chem.Lett.2000,11,1893 – 1895.; Bioorg.Med.Chem.2003,11 (13), 2843 – 2866.; Chem.Listy2003,97,1061 – 1069.), adopt in vitro test pattern to assess bacteriostasis property, tested object is: CA, CandidaalbicansATCC44859 (Candida albicans); CK, CandidakruseiE28 (candida krusei bacterium); CT, Candidatropicalis156 (Candida tropicalis); CG, Candidaglabrata20/I (Candida glabrata); TB, Trichosporonbeigelii1188 (Fructus Atriplicis Sibiricae trichosporon bacteria); AF, Aspergillusfumigatus231 (aspergillus fumigatus); AC, Absidiacorymbifera272 (umbrella branch colter bacterium); TM, Trichophytonmentagrophytes445 (Trichophyton mentagrophytes).Calendar year 2001, the people such as Pour report 3-aryl-5-acyloxymethyl-DHF-2-ketone series compound (Pour, M.;
m.; Buchta, V.; Kubanov á, P.;
m.; Ws ó l, V.; F á kov á, H.; Koudelka, P.; Pourov á, H.; Schiller, R.J.Med.Chem.2001,44 (17), 2701 – 2706.), adopt in vitro test pattern to assess bacteriostasis property, tested object is: CA1, CandidaalbicansATCC44859 (Candida albicans); CA2, CandidaalbicansATCC90028 (Candida albicans); CP, CandidaparapsilosisATCC22019 (Candida parapsilosis bacterium); CK1, CandidakruseiATCC6258 (candida krusei bacterium); CK2, CandidakruseiE28 (candida krusei bacterium); CT, Candidatropicalis156 (Candida tropicalis); CG, Candidaglabrata20/I (Candida glabrata); CL, Candidalusitaniae2446/I (Candida lusitaniae); TB, Trichosporonbeigelii1188 (Fructus Atriplicis Sibiricae trichosporon bacteria); AF, Aspergillusfumigatus231 (aspergillus fumigatus); AC, Absidiacorymbifera272 (umbrella branch colter bacterium); TM, Trichophytonmentagrophytes445 (Trichophyton mentagrophytes).
At present, due to the restriction of synthetic method, for 3-(4-aminomethyl phenyl)-5-ethyl-2, the research of 5-dihydrofuran-2-ketone and similar compound thereof mainly concentrates on human body pathogenic bacteria, as: Candida albicans, candida krusei, Candida tropicalis, Candida glabrata, Fructus Atriplicis Sibiricae trichosporon bacteria, aspergillus fumigatus, absidia corymbifera and Trichophyton mentagrophytes etc.About this compounds to tobacco mosaic virus, capsicum virus, tomato virus, sweet potato viruses, Potyvirus, melon virus, the plant viruses such as maize dwarf mosaic virus and cucumber Fusarium oxysporum, peanut Cercospora asparagagas, apple wheel line bacterium, Alternaria solani, gibberella saubinetii, rice bakanae disease bacterium, Sclerotinia sclerotiorum, phytophthora blight of pepper, Rhizoctonia cereali, corn stigma bacterium, watermelon anthrax-bacilus, potato late blight bacterium, the rejection of Rhizoctonia solani and botrytis cinerea phytopathogen does not see relevant report.
Summary of the invention
Technical problem to be solved by this invention is: provide 3-aryl-5-methylbutyrolactone compound to be used as the method for anti-plant virus agent, 3-aryl-5-methylbutyrolactone compound is used as anti-plant virus agent, tobacco mosaic virus (i.e. TMV), capsicum virus, tomato virus, sweet potato viruses, Potyvirus and melon virus and maize dwarf mosaic virus can be suppressed well, effectively can prevent and treat the virus disease of tobacco, capsicum, tomato, melon dish, grain, vegetables and legume crop, be particularly suitable for preventing and treating tobacco mosaic.
The present invention solves this technical problem adopted technical scheme: 3-aryl-5-methylbutyrolactone compound is used as the method for anti-plant virus agent, and step is as follows:
A. described 3-aryl-5-methylbutyrolactone compound is for having the compound of structure shown in general formula as follows (I):
Shown in general formula (I), the compound of structure comprises I again
aand I
btwo classes, concrete individuation compound is as follows:
B. above-mentioned 3-aryl-5-methylbutyrolactone compound is as follows as the method for anti-plant virus agent:
B-1. the step for activity of resisting tobacco mosaic virus is as follows:
The first step, tobacco mosaic virus is purified and concentration determination:
Tobacco mosaic virus is purified and concentration determination gives birth to survey room establishment tobacco mosaic virus SOP regulation enforcement with reference to Nankai University's element, and viral crude extract is after 2 polyethylene glycol centrifugal treating, and measure concentration, 4 DEG C of refrigerations are for subsequent use;
Second step, the preparation of the individuation compound liquid medicine of above-mentioned 3-aryl-5-methylbutyrolactone compound:
The individuation compound 40mg weighing above-mentioned 3-aryl-5-methylbutyrolactone compound, as former medicine, then adds DMF0.4mL and dissolves in this former medicine, and obtained 1 × 10
5μ g/mL mother liquor, then to be diluted to test concentrations with the Tween 80 aqueous solution that mass percent concentration is 1 ‰ be 500 μ g/mL or 100 μ g/mL, prepares to obtain the individuation compound liquid medicine of above-mentioned 3-aryl-5-methylbutyrolactone compound thus;
3rd step, acts in vitro:
The western Tobacco Leaves of frictional inoculation 3 – 5 leaf phase coral, with running water, virus concentration is 10 μ g/mL, receives after doing and cuts, along arteries and veins in leaf to cuing open, left and right half leaf be dipped in respectively mass percent concentration be 1 ‰ the Tween 80 aqueous solution and the individuation compound liquid medicine of above-mentioned 3-aryl-5-methylbutyrolactone compound prepared of second step in, take out after 30min, under normal temperature illumination condition, moisturizing is cultivated, every 3 leaves are repeat for 1 time, repeat 3 times, within 3 days, record scab number afterwards, calculate preventive effect;
4th step, live body protective effect:
Select the western cigarette of 3 – 5 leaf phase coral of growing way uniformity, the individuation compound liquid medicine of the above-mentioned 3-aryl-5-methylbutyrolactone compound that second step is prepared is executed in complete stool spraying, often process and repeat for 3 times, and the Tween 80 aqueous solution contrast that mass percent concentration is 1 ‰ is set, after 24h, blade face spreading 500 order diamond dust, virus liquid is dipped with writing brush, 2 times are dabbed along offshoot direction on full blade face, with palm support below blade, virus concentration 10 μ g/mL, inoculates rear running water, within 3 days, record scab number afterwards, calculate preventive effect;
5th step, live body therapeutic action:
Select the western cigarette of 3 – 5 leaf phase coral of growing way uniformity, with the full leaf virus inoculation of writing brush, virus concentration is 10 μ g/mL, inoculate rear running water, after blade face is received and done, the above-mentioned 3-aryl-5-methylbutyrolactone compound drug solution of second step preparation is executed in complete stool spraying, often process and repeat for 3 times, and the Tween 80 aqueous solution contrast that mass percent concentration is 1 ‰ is set, within 3 days, record scab number afterwards, calculate preventive effect;
6th step, live body passivation:
Select the western cigarette of 3 – 5 leaf phase coral of growing way uniformity, the individuation compound liquid medicine of the above-mentioned 3-aryl-5-methylbutyrolactone compound prepared by second step is with after isopyknic viral juice mixing passivation 30min, frictional inoculation, virus concentration is 20 μ g/mL, namely use running water after inoculation, repeat 3 times, the Tween 80 aqueous solution contrast that mass percent concentration is 1 ‰ is set, within 3 days, count scab number afterwards, result of calculation;
B-2. the step in vitro Fungicidally active is as follows:
Biomass growth rate determination method and Plating: the individuation compound of above-mentioned for 3mg 3-aryl-5-methylbutyrolactone compound is dissolved in 0.03mL acetone, then being diluted to test concentrations with the aqueous solution containing 200 μ g/mL Tween 80s is 50mg/kg, then respectively drawing 1mL liquid injects in culture dish corresponding with it, add 9mL medium respectively again, the pastille making 50 μ g/mL after shaking up is dull and stereotyped, blank is done with the flat board adding 1mL sterile purified water, bacterium dish is cut along mycelia outer rim with the card punch of diameter 4mm, move on pastille flat board, often process in triplicate, culture dish is placed in 24 ± 1 DEG C of constant incubators and cultivates, 48h " Invest, Then Investigate " respectively processes bacterium dish expansion diameter, average, compare with blank and calculate relative bacteriostasis rate,
B-3. the step of live body Fungicidally active is as follows:
Plant spray-on process: weigh the compound of body one by one in the above-mentioned 3-aryl of 30mg-5-methylbutyrolactone compound, be dissolved in 0.3mL dimethyl sulfoxide (DMSO), then the Tween 80 aqueous solution that mass percent concentration is 1 ‰ is added, be mixed with the spraying with medicament that test concentrations is 200 μ g/mL, greenhouse by solar heat is incubated at, after cucumber rough leaf is launched completely, with above-mentioned spraying with medicament spraying process for examination cucumber, wheat seedling, corn seedling, spouting liquid 1mL/ process, atomisation pressure is 0.7kg/cm
2, spraying distance is 15cm, and the heart stage process of wheat one leaf one, method is identical with cucumber processing procedure, and corn seedling processing method is identical with cucumber processing procedure, 24h after chemicals treatment, and cucumber grey mold and cucumber downy mildew all adopt spray inoculation 5 × 10
5the cucumber true leaf blade back of sporangia suspension after chemicals treatment of individual/mL, be that water soaking mode stops to blade, 24h is cultivated in dark situation moisturizing, after move to greenhouse under normally cultivate, 48h " Invest, Then Investigate " result, wheat seedling then adopts sedimentation inoculation method, connect 7 days investigation results after bacterium, result investigation adopts stage division, represents anosis, i.e. inhibiting rate 100% with " 100 " level; The occurring degree that the representative of " 0 " level is the most serious, inhibiting rate is 0, record result.
Above-mentioned 3-aryl-5-methylbutyrolactone compound is used as the method for anti-plant virus agent, the I that shown in described general formula (I), the compound of structure comprises
aand I
bconcrete individuation compound in two classes is all known compound, obtains by the known approach such as being purchased, and other involved reagent also obtain by the known approach such as being purchased.
The invention has the beneficial effects as follows: the disease caused by plant pathogenic fungi, account for 70 ~ 80% of plant disease.Agricultural sector proposes the ten large difficult treatment evils of China crop and fruit tree: rice blast, banded sclerotial blight, bacterial leaf-blight, stripe rust of wheat, cotton verticillium wilt, fusarium wilt, corn northern and southern leaf blight, black rot of sweet potato, citrus yellow shoot disease, apple canker.According to statistics, the grain drop in production caused because of fungi every year reaches 1.25 hundred million tons.The viroses of plant (frequent species more than 2000 kind) of a great variety, control is difficulty very, and have the title of " plant cancer ", its harm is only second to fungal disease.According to statistics, the economic loss that the annual crop plants virus disease in the whole world causes reaches 20,000,000,000 dollars, wherein only tobacco mosaic virus (Tobaccomosaicvirus, TMV) economic loss caused every year is more than 100,000,000 dollars of (BosL.100yearsofvirology:fromvitalismviamolecularbiologyt ogeneticengineering.Trendsinmicrobiology, 2000,8 (2): 82-87).Mycosis and the virus disease of crop cause extreme loss to agricultural production, and demand and the exploitation of Antiphytoviral medicament and pathogenic bacteria inhibitor receive very large concern always.
Be used as in the method for anti-plant virus agent at 3-aryl-5-methylbutyrolactone compound of the present invention, 3-aryl-5-methylbutyrolactone Compound I
a-1 ~ I
a-9 and I
b-1 ~ I
b-9 in the concentration of 500 μ g/mL to the inhibiting rate of tobacco mosaic virus up to more than 60%, exceed commercial varieties virus A, activity (all only having 50% at 500 μ g/mL inhibiting rates) that virazole, DADHT and DHT suppress tobacco mosaic virus.Especially Compound I
b-9 500 μ g/mL isolated activities, live body passivation, live body treatment and live body protection in inhibiting rate be respectively 61.2%, 51.6%, 57.1% and 55.8%, commercial varieties virazole inhibiting rate is respectively 40.6%, 39.5%, 37.4% and 39.8% under identical testing conditions.
In addition, 3-aryl-5-methylbutyrolactone Compound I
a-1 ~ I
a-9 show higher bactericidal activity to 14 kinds of fungies, especially Compound I
a-3, I
a-4, I
a-5 and I
a-6 bactericidal activities of all doing well to multiple fungi are suitable with tpn with commercial varieties carbendazim to 14 kinds of fungi isolated activities under 50mg/kg concentration; Compound I under 50mg/kg concentration
a-3, I
a-4, I
a-5 and I
a-6 pairs of peanut Cercospora asparagagas, Alternaria solani isolated activities are obviously better than commercial varieties carbendazim and tpn, possess great Development volue.Therefore say, relative to prior art, the inventive method has significant progressive and very outstanding economic benefit.
Embodiment
Embodiment 1
A. described 3-aryl-5-methylbutyrolactone compound is for having the compound of structure shown in general formula as follows (I):
Shown in general formula (I), the compound of structure comprises I again
aand I
btwo classes, concrete individuation compound is as follows:
B. above-mentioned 3-aryl-5-methylbutyrolactone compound is as follows as the method for anti-plant virus agent:
B-1. the step for activity of resisting tobacco mosaic virus is as follows:
The first step, tobacco mosaic virus is purified and concentration determination:
Tobacco mosaic virus is purified and concentration determination gives birth to survey room establishment tobacco mosaic virus SOP regulation enforcement with reference to Nankai University's element, and viral crude extract is after 2 polyethylene glycol centrifugal treating, and measure concentration, 4 DEG C of refrigerations are for subsequent use;
Second step, the individual Compound I of above-mentioned 3-aryl-5-methylbutyrolactone compound
athe preparation of-1 liquid medicine:
Weigh the individual Compound I of above-mentioned 3-aryl-5-methylbutyrolactone compound
a-140mg, as former medicine, then adds DMF0.4mL and dissolves in this former medicine, and obtained 1 × 10
5μ g/mL mother liquor, then to be diluted to test concentrations with the Tween 80 aqueous solution that mass percent concentration is 1 ‰ be 500 μ g/mL, prepares to obtain the individual Compound I of above-mentioned 3-aryl-5-methylbutyrolactone compound thus
a-1 liquid medicine;
3rd step, acts in vitro:
The western Tobacco Leaves of frictional inoculation 3 – 5 leaf phase coral, with running water, virus concentration is 10 μ g/mL, receive after doing and cut, along arteries and veins in leaf to cuing open, left and right half leaf is dipped in the Tween 80 aqueous solution and the individual Compound I of above-mentioned 3-aryl-5-methylbutyrolactone compound prepared of second step that mass percent concentration is 1 ‰ respectively
ain-1 liquid medicine, take out after 30min, under normal temperature illumination condition, moisturizing is cultivated, and every 3 leaves are repeat for 1 time, repeat 3 times, within 3 days, record scab number afterwards, calculate preventive effect;
4th step, live body protective effect:
Select the western cigarette of 3 – 5 leaf phase coral of growing way uniformity, the individual Compound I of the above-mentioned 3-aryl-5-methylbutyrolactone compound that second step is prepared is executed in complete stool spraying
a-1 liquid medicine, often process and repeat for 3 times, and the Tween 80 aqueous solution contrast that mass percent concentration is 1 ‰ is set, after 24h, blade face spreading 500 order diamond dust, dip virus liquid with writing brush, dab 2 times on full blade face along offshoot direction, with palm support below blade, virus concentration 10 μ g/mL, inoculate rear running water, within 3 days, record scab number afterwards, calculate preventive effect;
5th step, live body therapeutic action:
Select the western cigarette of 3 – 5 leaf phase coral of growing way uniformity, with the full leaf virus inoculation of writing brush, virus concentration is 10 μ g/mL, inoculates rear running water, after blade face is received and done, the individual Compound I of the above-mentioned 3-aryl-5-methylbutyrolactone compound drug of second step preparation is executed in complete stool spraying
a-1 solution, often processes and repeats for 3 times, and arranges the Tween 80 aqueous solution contrast that mass percent concentration is 1 ‰, within 3 days, records scab number afterwards, calculates preventive effect;
6th step, live body passivation:
Select the western cigarette of 3 – 5 leaf phase coral of growing way uniformity, by the individual Compound I of the above-mentioned 3-aryl-5-methylbutyrolactone compound that second step is prepared
a-1 liquid medicine with after isopyknic viral juice mixing passivation 30min, frictional inoculation, virus concentration is 20 μ g/mL, namely use running water after inoculation, repeat 3 times, the Tween 80 aqueous solution contrast that mass percent concentration is 1 ‰ is set, within 3 days, count scab number afterwards, result of calculation;
The individual Compound I of above-mentioned 3-aryl-5-methylbutyrolactone compound
athe measurement result of the activity of resisting tobacco mosaic virus of-1 is in table 1.
B-2. the step in vitro Fungicidally active is as follows:
Biomass growth rate determination method and Plating: by the individual Compound I of above-mentioned for 3mg 3-aryl-5-methylbutyrolactone compound
a-1 is dissolved in 0.03mL acetone, then being diluted to test concentrations with the aqueous solution containing 200 μ g/mL Tween 80s is 50mg/kg, then respectively drawing 1mL liquid injects in culture dish corresponding with it, add 9mL medium respectively again, the pastille making 50 μ g/mL after shaking up is dull and stereotyped, blank is done with the flat board adding 1mL sterile purified water, bacterium dish is cut along mycelia outer rim with the card punch of diameter 4mm, move on pastille flat board, often process in triplicate, culture dish is placed in 24 ± 1 DEG C of constant incubators and cultivates, 48h " Invest, Then Investigate " respectively processes bacterium dish expansion diameter, average, compare with blank and calculate relative bacteriostasis rate.
The individual Compound I of above-mentioned 3-aryl-5-methylbutyrolactone compound
athe in vitro Fungicidally active of-1 the results are shown in Table 2;
B-3. the step of live body Fungicidally active is as follows:
Plant spray-on process: the individual Compound I weighing 30mg above-mentioned 3-aryl-5-methylbutyrolactone compound
a-1, be dissolved in 0.3mL dimethyl sulfoxide (DMSO), then the Tween 80 aqueous solution that mass percent concentration is 1 ‰ is added, be mixed with the spraying with medicament that test concentrations is 200 μ g/mL, Nankai University Sheng Ce building greenhouse by solar heat is incubated at, after cucumber rough leaf is launched completely, with above-mentioned spraying with medicament spraying process for examination cucumber, wheat seedling, corn seedling, spouting liquid 1mL/ process, atomisation pressure is 0.7kg/cm
2, spraying distance is 15cm, and the heart stage process of wheat one leaf one, method is identical with cucumber processing procedure, and corn seedling processing method is identical with cucumber processing procedure, 24h after chemicals treatment, and cucumber grey mold and cucumber downy mildew all adopt spray inoculation 5 × 10
5the cucumber true leaf blade back of sporangia suspension after chemicals treatment of individual/mL, be that water soaking mode stops to blade, 24h is cultivated in dark situation moisturizing, after move to greenhouse under normally cultivate, 48h " Invest, Then Investigate " result, wheat seedling then adopts sedimentation inoculation method, connect 7 days investigation results after bacterium, result investigation adopts stage division, represents anosis, i.e. inhibiting rate 100% with " 100 " level; The occurring degree that the representative of " 0 " level is the most serious, inhibiting rate is 0, record.
The individual Compound I of above-mentioned 3-aryl-5-methylbutyrolactone compound
athe test result of the live body Fungicidally active of-1 is in table 3.
Embodiment 2
Except the individual Compound I of second step above-mentioned 3-aryl-5-methylbutyrolactone compound
ain the preparation of-1 liquid medicine, weigh the individual Compound I of above-mentioned 3-aryl-5-methylbutyrolactone compound
a-140mg, as former medicine, then adds DMF0.4mL and dissolves in this former medicine, and obtained 1 × 10
5μ g/mL mother liquor, then to be diluted to test concentrations with the Tween 80 aqueous solution that mass percent concentration is 1 ‰ be that outside 100 μ g/mL, other are with embodiment 1.
Embodiment 3
Except the individuation compound of above-mentioned 3-aryl-5-methylbutyrolactone compound is I
aoutside-2, other are with embodiment 1.
Embodiment 4
Except the individuation compound of above-mentioned 3-aryl-5-methylbutyrolactone compound is I
aoutside-2, other are with embodiment 2.
Embodiment 5
Except the individuation compound of above-mentioned 3-aryl-5-methylbutyrolactone compound is I
aoutside-3, other are with embodiment 1.
Embodiment 6
Except the individuation compound of above-mentioned 3-aryl-5-methylbutyrolactone compound is I
aoutside-3, other are with embodiment 2.
Embodiment 7
Except the individuation compound of above-mentioned 3-aryl-5-methylbutyrolactone compound is I
aoutside-4, other are with embodiment 1.
Embodiment 8
Except the individuation compound of above-mentioned 3-aryl-5-methylbutyrolactone compound is I
aoutside-4, other are with embodiment 2.
Embodiment 9
Except the individuation compound of above-mentioned 3-aryl-5-methylbutyrolactone compound is I
aoutside-5, other are with embodiment 1.
Embodiment 10
Except the individuation compound of above-mentioned 3-aryl-5-methylbutyrolactone compound is I
aoutside-5, other are with embodiment 2.
Embodiment 11
Except the individuation compound of above-mentioned 3-aryl-5-methylbutyrolactone compound is I
aoutside-6, other are with embodiment 1.
Embodiment 12
Except the individuation compound of above-mentioned 3-aryl-5-methylbutyrolactone compound is I
aoutside-6, other are with embodiment 2.
Embodiment 13
Except the individuation compound of above-mentioned 3-aryl-5-methylbutyrolactone compound is I
aoutside-7, other are with embodiment 1.
Embodiment 14
Except the individuation compound of above-mentioned 3-aryl-5-methylbutyrolactone compound is I
aoutside-7, other are with embodiment 2.
Embodiment 15
Except the individuation compound of above-mentioned 3-aryl-5-methylbutyrolactone compound is I
aoutside-8, other are with embodiment 1.
Embodiment 16
Except the individuation compound of above-mentioned 3-aryl-5-methylbutyrolactone compound is I
aoutside-8, other are with embodiment 2.
Embodiment 17
Except the individuation compound of above-mentioned 3-aryl-5-methylbutyrolactone compound is I
aoutside-9, other are with embodiment 1.
Embodiment 18
Except the individuation compound of above-mentioned 3-aryl-5-methylbutyrolactone compound is I
aoutside-9, other are with embodiment 2.
Embodiment 19
Except the individuation compound of above-mentioned 3-aryl-5-methylbutyrolactone compound is I
boutside-1, other are with embodiment 1.
Embodiment 20
Except the individuation compound of above-mentioned 3-aryl-5-methylbutyrolactone compound is I
boutside-1, other are with embodiment 2.
Embodiment 21
Except the individuation compound of above-mentioned 3-aryl-5-methylbutyrolactone compound is I
boutside-2, other are with embodiment 1.
Embodiment 22
Except the individuation compound of above-mentioned 3-aryl-5-methylbutyrolactone compound is I
boutside-2, other are with embodiment 2.
Embodiment 23
Except the individuation compound of above-mentioned 3-aryl-5-methylbutyrolactone compound is I
boutside-3, other are with embodiment 1.
Embodiment 24
Except the individuation compound of above-mentioned 3-aryl-5-methylbutyrolactone compound is I
boutside-3, other are with embodiment 2.
Embodiment 25
Except the individuation compound of above-mentioned 3-aryl-5-methylbutyrolactone compound is I
boutside-4, other are with embodiment 1.
Embodiment 26
Except the individuation compound of above-mentioned 3-aryl-5-methylbutyrolactone compound is I
boutside-4, other are with embodiment 2.
Embodiment 27
Except the individuation compound of above-mentioned 3-aryl-5-methylbutyrolactone compound is I
boutside-5, other are with embodiment 1.
Embodiment 28
Except the individuation compound of above-mentioned 3-aryl-5-methylbutyrolactone compound is I
boutside-5, other are with embodiment 2.
Embodiment 29
Except the individuation compound of above-mentioned 3-aryl-5-methylbutyrolactone compound is I
boutside-6, other are with embodiment 1.
Embodiment 30
Except the individuation compound of above-mentioned 3-aryl-5-methylbutyrolactone compound is I
boutside-6, other are with embodiment 2.
Embodiment 31
Except the individuation compound of above-mentioned 3-aryl-5-methylbutyrolactone compound is I
boutside-7, other are with embodiment 1.
Embodiment 32
Except the individuation compound of above-mentioned 3-aryl-5-methylbutyrolactone compound is I
boutside-7, other are with embodiment 2.
Embodiment 33
Except the individuation compound of above-mentioned 3-aryl-5-methylbutyrolactone compound is I
boutside-8, other are with embodiment 1.
Embodiment 34
Except the individuation compound of above-mentioned 3-aryl-5-methylbutyrolactone compound is I
boutside-8, other are with embodiment 2.
Embodiment 35
Except the individuation compound of above-mentioned 3-aryl-5-methylbutyrolactone compound is I
boutside-9, other are with embodiment 1.
Embodiment 36
Except the individuation compound of above-mentioned 3-aryl-5-methylbutyrolactone compound is I
boutside-9, other are with embodiment 2.
The anti-TMV active testing result of table 1. above-mentioned 3-aryl-5-methylbutyrolactone compound
In table 1, inhibiting rate (%)=[(contrast withered spot number-process withered spot number)/contrast withered spot number] × 100%, virazole is tester.
As seen from Table 1, the I in above-mentioned 3-aryl-5-methylbutyrolactone compound
a-1 ~ I
a-7 show poisoning, but Compound I
a-8 and I
a-9 show higher anti-TMV activity; I in above-mentioned 3-aryl-5-methylbutyrolactone compound
b-1 ~ I
b-9 show higher anti-TMV activity, and resisting tobacco mosaic virus live body activity is obviously better than commercial varieties virazole, particularly Compound I
b-1, I
b-3 and I
b-9, possess great Development volue.
The in vitro bactericidal activity test result of table 2. above-mentioned 3-aryl-5-methylbutyrolactone compound
As seen from Table 2, the I in above-mentioned 3-aryl-5-methylbutyrolactone compound
a-1 ~ I
a-9 show higher bactericidal activity to 14 kinds of fungies, especially Compound I
a-4, I
a-5, I
a-6 and I
a-7 bactericidal activities of all doing well to multiple fungi are suitable with tpn with commercial varieties carbendazim to 14 kinds of fungi isolated activities under 50mg/kg concentration; Compound I under 50mg/kg concentration
a-4, I
a-5, I
a-6 and I
a-7 pairs of peanut Cercospora asparagagas, Alternaria solani isolated activities are obviously better than commercial varieties carbendazim and tpn, possess great Development volue.
The above-mentioned 3-aryl of table 3.-5-methylbutyrolactone compound live body bactericidal activity test result
As seen from Table 3, the I in above-mentioned 3-aryl-5-methylbutyrolactone compound
a-1 ~ I
a-7 show certain bactericidal activity to 7 kinds of fungies, especially Compound I
a-3 live body bactericidal activities that multiple fungi is all done well, under 200 μ g/mL concentration, excellent bactericidal activity is revealed to corn rust, sclerotinia rot of colza, rice sheath blight disease, gray mold of cucumber and Cucumber Target Leaf Spot live body test chart, possess great Development volue.
In above-described embodiment, the I that shown in described general formula (I), the compound of structure comprises
aand I
bconcrete individuation compound in two classes is all known compound, obtains by the known approach such as being purchased, and other involved reagent also obtain by the known approach such as being purchased.
Claims (1)
1.3-aryl-5-methylbutyrolactone compound is used as the purposes of anti-plant virus agent, and it is characterized in that, described 3-aryl-5-methylbutyrolactone compound is selected from following compound:
Described plant virus is tobacco mosaic virus.
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| CN201510509290.7A CN105010342B (en) | 2014-07-18 | 2014-07-18 | Method for using 3-aryl-5-methylbutyrolactone compounds as plant pathogenic fungus killing agent |
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| CN105123175B (en) * | 2015-07-22 | 2018-01-09 | 四川省农业科学院作物研究所 | A kind of inoculation method of grey leaf spot disease of maize |
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| CN101820763A (en) * | 2007-10-02 | 2010-09-01 | 拜尔农作物科学股份公司 | Methods of improving plant growth |
| WO2014050894A1 (en) * | 2012-09-27 | 2014-04-03 | 日本曹達株式会社 | Ascorbic acid-related compound and anti-plant-virus agent |
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| CN101820763A (en) * | 2007-10-02 | 2010-09-01 | 拜尔农作物科学股份公司 | Methods of improving plant growth |
| WO2014050894A1 (en) * | 2012-09-27 | 2014-04-03 | 日本曹達株式会社 | Ascorbic acid-related compound and anti-plant-virus agent |
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| Title |
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| Synthesis and Antiviral Activities of Phenanthroindolizidine Alkaloids and Their Derivatives;Kailiang Wang et al.;《J. Agric. Food Chem.》;20091210;第58卷(第5期);2703-2709 * |
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