CN1868277A - Application of benzothidiazole derivatives as activator for plant disease-resistant agent - Google Patents

Application of benzothidiazole derivatives as activator for plant disease-resistant agent Download PDF

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CN1868277A
CN1868277A CN 200610027833 CN200610027833A CN1868277A CN 1868277 A CN1868277 A CN 1868277A CN 200610027833 CN200610027833 CN 200610027833 CN 200610027833 A CN200610027833 A CN 200610027833A CN 1868277 A CN1868277 A CN 1868277A
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application
formula
activator
rice
plant
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CN100486435C (en
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钱旭红
徐玉芳
赵振江
黄军海
田文红
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East China University of Science and Technology
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Abstract

An application of the benzothiabiazole as the disease resistance activating agent for preventing and treating the hoja blanca and blast of rice, the powdery mildew of melon, the necrosis host of Nicotiana tabacum L. var. Xanthi-NC, etc is disclosed.

Description

The application of diazosulfide derivative in the plant disease-resistant activator
Technical field
The present invention relates to a kind of purposes of diazosulfide derivative, specifically, relate to its application in the plant disease-resistant activator.
Background technology
Mostly the tradition agricultural chemicals is that to kill pest be purpose, but is difficult to escape the generation of " pesticide hazards ".Under the pressure of the pressure of safety, ecology and environment aspect, the novel pesticide construction cycle prolongs gradually, and the input funds increase year by year, and development-success ratio descends day by day.Although chemical pesticide is still being brought into play the important function that alternate manner can't replace at present, the purpose of utilizing the system of defense of plant self to reach preventing disease pest control will be one of developing direction of agricultural chemicals from now on.
Salicylic acid and dichloro-isonicotinic acid are to find to have the disease-resistant compound that activates activity the earliest, but effect is unsatisfactory.Time and the level of Induced by Salicylic Acid SAR (Systemic Acquired Resistance) are often unpredictable; The effective dose of dichloro-isonicotinic acid is bigger to the toxicity of crop.Japanese Mingzhi drugmaker was that the synthetic allyl isothiazole (Probenazole) of raw material is commercial the earliest plant activator with the ortho-sulfonic acid yl benzoic acid in 1973.This plant activator all has inhibitory action to fungi and bacteriosis, but since not enough to its mechanism of action understanding at that time, think that its effect is slow, so do not obtain very great development always.Nineteen ninety-five, vapour crust-Jia Ji company has successfully developed Acibenzolar-phendioxin, and 2,3-thiadiazoles-7-carboxylic acid sulfo-methyl esters (BTH or Acibenzolar), and after having illustrated its mechanism of action just makes the allyl isothiazole of Japanese Mingzhi drugmaker obtain new life.
BTH (being Acibenzolar Acibenzolar CGA245704 again) is a kind of brand-new plant protection products-plant disease-resistant activator (plant activator) that is different from traditional agricultural chemicals, is commercial at present plant disease-resistant activator product (1996 is that trade name register with Bion 50WG, in Switzerland with Unix Bion 63WG in Germany).
Chinese patent (ZL 03116948.1) has been reported a kind of purposes of diazosulfide derivative, promptly as cell induction agent (Elicitor), its effect is the material that is added in order to increase some secondary metabolite in the cell cultivation process in the cells in-vitro cultivation.The present inventor finds that the part diazosulfide derivative of having reported not only can be used as the cell induction agent after deeply a large amount of and careful screening, and has good disease-resistant activation activity.Therefore, the new purposes that discloses this part diazosulfide derivative just becomes purpose of the present invention.
Summary of the invention
The object of the invention is, a kind of new purposes of diazosulfide derivative is provided.
The said diazosulfide derivative of the present invention has structure shown in the formula (1):
Figure A20061002783300041
In the formula (1),
Figure A20061002783300042
Figure A20061002783300043
The preparation method of said diazosulfide derivative does not repeat them here referring to ZL 03116948.1.
A purposes of compound shown in the formula (1) is the application in anti-bacterial blight of rice;
Another purposes of compound shown in the formula (1) is the application in anti-rice blast;
Another purposes of compound shown in the formula (1) is the application in anti-melon anthracnose;
Another purposes of compound shown in the formula (1) is the application in anti-cucurbits powdery mildew.
A purposes of compound shown in the formula (1) is the application in the withered spot host of anti-coral west cigarette (Nicotiana tabacum L.var.xanthi-NC).
Meaning of the present invention is, has disclosed the new purposes of a class diazosulfide derivative, and promptly such diazosulfide derivative not only can be used for the plant cell derivant, but also can be used as the plant disease-resistant activator.Widened the application of diazosulfide derivative.
Embodiment
The present invention is further elaborated below by embodiment (screening technique that the present invention adopts and gained The selection result), and its purpose only is better to understand content of the present invention.
Embodiment 1
1. for examination object disease:
1.1 potted plant mensuration: a kind of bacterial disease: i.e. bacterial blight of rice; Three kinds of fungal diseases: i.e. rice blast, melon anthracnose and cucurbits powdery mildew.
2. for studying thing: paddy rice, cucumber.
3. reagent agent concentration is set:
3.1 potted plant mensuration: the medicament bacterial blight of rice of participating in the experiment 200mg/L, rice blast 100mg/L and 200mg/L, melon anthracnose, cucurbits powdery mildew 50mg/L and 100mg/L.
4. test method:
4.1 potted plant mensuration: good various crops of sowing in advance, and quantitatively take by weighing sample with the DMF dissolving and add proper amount of surfactant, are diluted with water to setting concentration.Adopt roll-back method to carry out drug treating 5~6 times, disposablely then inoculate pathogen simultaneously in inoculation the first seven day, four days, two days, one day and when natural gift.Observe medicine on the plant corpus behind different time to disease symptom generation Influence and Development, judge its control efficiency to disease.
4.1.1 bacterial blight of rice: on the big rice seedling of potted plant 2 months paddy rice (round bar phase), handle by last 5 spray medicines.If blank, 3 repeat.After the last medication second day, Xanthomonas oryzae is inoculated in two blade stage casings under every strain rice seedling lobus cardiacus with double pin stab inoculation.After morbidity is stable, give birth to the survey SOP record state of an illness,, calculate control efficiency with the blank ratio by the initiative center.
4.1.2 rice blast: begin to handle by 6 spray medicines from potted plant 2~3 leaf phase paddy rice seedlings, establish blank, 3 repeat.After the last medication, when the daily use Pyricularia oryzae divide spore suspension (4.0 * 105/ml) spray inoculation is in being on 5~6 leaf paddy rice seedlings, put humidistat wet about 30 hours of the insulation of shading, remove the thing that shades, be equipped with the illumination humidistat, give birth to the survey SOP record state of an illness by the initiative center, calculate control efficiency.
4.1.3 melon anthracnose: from cotyledon later stage cucumber seedling, handle by 5 spraying medicine methods, establish blank, 3 repeat.Ought be everyday after the last medication, (spray inoculation of 5..0 * 105/ml) is on the cucumber leaves that 2 leaf periods are arranged with melon anthrax bacteria spore suspension, after putting humidistat and shading 30 hours, in humidistat, take out, put under the illumination, give birth to survey SOP by the initiative center, scab number on the counting blade calculates control efficiency.
4.1.4 cucurbits powdery mildew: cucumber seedling breeding time and medication are handled the same, (6~8 * 104/ml), still be equipped with the illumination greenhouse behind the spray inoculation of white powder germ spore suspensions of inoculation, do not preserve moisture, give birth to survey SOP by the initiative center, counting leaf spot lesion number calculates control efficiency.
5. result of the test: see Table 1~table 4.
Table 1
Figure A20061002783300061
Table 2
Figure A20061002783300062
Table 3
Table 4
Control efficiency in table 1~table 4 (%) is to be calculated as follows and to get:
Figure A20061002783300073
By listed measurement result in table 1~table 4 as can be known: when R is CH 2CF 3Or CH 2CH 2CF 3The time, sample is all effective to melon powdery mildew, anthracnose etc., and is similar to contrast agents 50%BTH, but will get well according to medicament the sick effect comparison of rice.
Embodiment 2
1, materials and methods
1.1 test material
The withered spot host of coral west cigarette (Nicotiana tabacum L.var.xanthi-NC),
Contrast medicament: phendioxin, 2,3-thiadiazoles-7-carboxylic acid sulfo-methyl esters (BTH).
1.2 induce the effect test method
On the tobacco plant of the coral of 5~6 leaf ages west, choose the blade (leaf normal, anosis no worm) that is applicable to test, earlier in the base portion dispenser, spraying medicine concentration is 100 μ g/mL, behind the certain hour of interval with writing brush with standby malicious source (3.0 * 10 -3) evenly be put on the blade that spreads corundum, every plant is selected 3~5 tobacco leaves inoculation TMV, and the tobacco of not dispenser is observed drug effect and poisoning situation every day for contrast, check result and be calculated as follows to such an extent that induce effect (%) after 7 days.
X = CT - T CK × 100 %
Wherein: X: induce effect (%); CK: the tobacco of not dispenser connects the withered spot number of malicious leaf (individual); T: the withered spot number (individual) of the tobacco sheet leaf of dispenser
2, the measurement result of induction experiment: see Table 5
Table 5
Figure A20061002783300082
As shown in Table 5, shown in the formula (1), and R is CH 2CF 2CF 3Compound and the induced activity of BTH quite active under 100 μ g/mL concentration.

Claims (5)

1, the application of compound in anti-bacterial blight of rice shown in a kind of formula (1),
Figure A2006100278330002C1
In the formula (1), R is CH 2CF 3, CH 2CF 2CF 3,
Figure A2006100278330002C3
Or
2, the application of compound in anti-rice blast shown in a kind of formula (1).
3, the application of compound shown in a kind of formula (1) in anti-melon anthracnose.
4, the application of compound in anti-cucurbits powdery mildew shown in a kind of formula (1).
5, the application of compound shown in a kind of formula (1) in the withered spot host of anti-coral west cigarette (Nicotiana tabacum L.var.xanthi-NC).
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CN101836640A (en) * 2010-03-04 2010-09-22 中国农业科学院蔬菜花卉研究所 Application of elicitor in controlling soil-borne diseases of garden crops
CN101492429B (en) * 2008-12-10 2010-12-15 上海泰禾(集团)有限公司 Purification method for benzo-[1,2,3]-thiadiazole-7-methanoic acid trifluoro ethyl ester
CN102532058A (en) * 2011-12-29 2012-07-04 华东理工大学 Application of aphtho-[1, 2 and 3] benzothiadiazola-7-carboxylic ester derivative serving as plant disease-resistant activating agent
CN102532059A (en) * 2011-12-29 2012-07-04 华东理工大学 Application of naphtho-[1, 2 and 3] benzothiadiazola fluorine containing derivative serving as plant disease-resistant activating agent
CN102827090A (en) * 2012-09-03 2012-12-19 华东理工大学 Benzotriazol compound and application thereof
CN103509039A (en) * 2012-06-21 2014-01-15 华东理工大学 Thienothiadiazole derivatives and application of same as plant resistance activator
CN103651460A (en) * 2012-09-25 2014-03-26 陕西美邦农药有限公司 Pesticide composition containing fluorine azole activated ester and methoxy acrylic esters
CN103651413A (en) * 2012-09-21 2014-03-26 陕西美邦农药有限公司 Fluorine azole activated ester and triazoles sterilization composition
CN103651414A (en) * 2012-09-21 2014-03-26 陕西美邦农药有限公司 Fungicidal composition containing fluoro-azole acibenzolar and methoxyl acrylate
CN103651415A (en) * 2012-09-26 2014-03-26 陕西美邦农药有限公司 Bactericidal composition containing fluorine azole activated ester and triazoles
CN106857559A (en) * 2017-03-07 2017-06-20 江苏省农业科学院 A kind of method of utilization salicylic acid and the like the medicament reduction black streaked dwarf virus of rice incidence of disease
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CN101492429B (en) * 2008-12-10 2010-12-15 上海泰禾(集团)有限公司 Purification method for benzo-[1,2,3]-thiadiazole-7-methanoic acid trifluoro ethyl ester
CN101836640B (en) * 2010-03-04 2014-06-11 中国农业科学院蔬菜花卉研究所 Application of elicitor in controlling soil-borne diseases of garden crops
WO2011107030A1 (en) * 2010-03-04 2011-09-09 华东理工大学 Application of an elicitor in control of soil-born diseases of garden crops
CN101836640A (en) * 2010-03-04 2010-09-22 中国农业科学院蔬菜花卉研究所 Application of elicitor in controlling soil-borne diseases of garden crops
CN102532058A (en) * 2011-12-29 2012-07-04 华东理工大学 Application of aphtho-[1, 2 and 3] benzothiadiazola-7-carboxylic ester derivative serving as plant disease-resistant activating agent
CN102532059A (en) * 2011-12-29 2012-07-04 华东理工大学 Application of naphtho-[1, 2 and 3] benzothiadiazola fluorine containing derivative serving as plant disease-resistant activating agent
CN102532058B (en) * 2011-12-29 2016-11-09 华东理工大学 Benzo [1,2,3] thiadiazoles-7-carboxylic ester derivative is as the application of Plant activator
CN102532059B (en) * 2011-12-29 2016-11-02 华东理工大学 Benzo [1,2,3] thiadiazoles fluorine-containing derivant is as the application of Plant activator
CN103509039A (en) * 2012-06-21 2014-01-15 华东理工大学 Thienothiadiazole derivatives and application of same as plant resistance activator
CN103509039B (en) * 2012-06-21 2017-07-28 华东理工大学 Thieno thiadiazoles derivative and its application as Plant activator
CN102827090A (en) * 2012-09-03 2012-12-19 华东理工大学 Benzotriazol compound and application thereof
CN103651413B (en) * 2012-09-21 2015-09-09 陕西美邦农药有限公司 The bactericidal composition of a kind of fluorine azoles Acibenzolar and triazole type
CN103651414B (en) * 2012-09-21 2015-07-08 陕西美邦农药有限公司 Fungicidal composition containing fluoro-azole acibenzolar and methoxyl acrylate
CN103651414A (en) * 2012-09-21 2014-03-26 陕西美邦农药有限公司 Fungicidal composition containing fluoro-azole acibenzolar and methoxyl acrylate
CN103651413A (en) * 2012-09-21 2014-03-26 陕西美邦农药有限公司 Fluorine azole activated ester and triazoles sterilization composition
CN103651460B (en) * 2012-09-25 2015-07-08 陕西美邦农药有限公司 Pesticide composition containing fluorine azole activated ester and methoxy acrylic esters
CN103651460A (en) * 2012-09-25 2014-03-26 陕西美邦农药有限公司 Pesticide composition containing fluorine azole activated ester and methoxy acrylic esters
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CN103651415A (en) * 2012-09-26 2014-03-26 陕西美邦农药有限公司 Bactericidal composition containing fluorine azole activated ester and triazoles
CN104839175B (en) * 2012-09-26 2017-01-18 陕西美邦农药有限公司 Bactericidal composition comprising fluoazole active ester and triazoles
CN106857559A (en) * 2017-03-07 2017-06-20 江苏省农业科学院 A kind of method of utilization salicylic acid and the like the medicament reduction black streaked dwarf virus of rice incidence of disease
CN110204509A (en) * 2019-05-16 2019-09-06 华南农业大学 A kind of diazosulfide-selenium complexing nano object and its preparation method and application

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