CN108617670B - Application of sulfonamide compound in aphid prevention and control - Google Patents
Application of sulfonamide compound in aphid prevention and control Download PDFInfo
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- CN108617670B CN108617670B CN201810768150.5A CN201810768150A CN108617670B CN 108617670 B CN108617670 B CN 108617670B CN 201810768150 A CN201810768150 A CN 201810768150A CN 108617670 B CN108617670 B CN 108617670B
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
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- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for preventing and treating aphid by using sulfonamide compoundThe application of the sulfonamide compound has a structural formula shown in a formula II:
wherein R is1Represents hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 alkylthio, halogen, nitro, cyano, azido, hydroxyl or trifluoromethyl; r2Represents isopentenyl, C1-C10 alkyl, a phenyl ring, pyridine, thiazole, thiophene, pyrrole, furan, pyrazole, imidazole, pyran, pyrazine, pyrimidine, pyridazine, benzofuran, benzothiophene, indole, quinoline, trifluoromethyl or halogen. The pesticide prepared by adopting the compound of the formula II as an active ingredient has good aphid killing activity and shows low toxicity to non-target bees.
Description
The application is a divisional application of an invention patent application with the application number of '201610535020.8', the application date of 2016, 7 and 8 and the name of 'application of sulfonamide compounds in controlling agricultural pests'.
Technical Field
The invention relates to application of sulfonamide compounds in preventing and controlling agricultural pests.
Background
The new-generation pesticide with imidacloprid as the representative is a new-generation pesticide with milestone significance after organophosphorus, organochlorine, carbamate and pyrethroid. The insecticidal composition has the characteristics of high efficiency, wide insecticidal spectrum, outstanding prevention and control on piercing-sucking mouthpart pests, systemic root, contact killing and stomach poisoning effects, low residue, environmental friendliness, safety to mammals and aquatic organisms and the like, is widely applied, occupies the main share of the global insecticide market, and continuously increases the annual sales of the whole world to reach or exceed billions of dollars (Kagabu S.J.Agric.food chem.2011,59, 2887-.
Due to improper and improper use of pesticides, the resistance and cross-resistance of neonicotinoids is becoming increasingly evident, with imidacloprid being as resistant as tens to hundreds of times, even producing resistant races (NauenR. Bull. entomol. Res.1996,86, 165-. Honeybees are used as main pollinators in the nature, have important economic and ecological values, and the large-scale rapid reduction of the population quantity of the honeybees draws great attention in all the world. Scholars at home and abroad speculate that the cause of the bee collapse syndrome can be factors such as pesticides, pathogens, parasites or deterioration of living environment, but researches indicate that the threat of the neonicotinoid insecticide to bee colonies is far greater than that of other factors. The application of the neonicotinoid insecticide can cause the hypomotility function and the memory dysfunction of bees, affect the olfaction, foraging and navigation abilities, and show a series of lethal and sublethal phenomena such as the loss of the ability of returning to honeycombs. The british scientific society states that bees infected with parasitic fungi have reduced immunity and cause their death, and that neonicotinoid insecticides have immunosuppressive effects on non-target organisms and accelerate the invasion of pathogenic bacteria into organisms (ratnieksf.l. Science,2010,327(5962), 152-. It is seen that the impact of neonicotinoid insecticides on bee populations has been widely recognized, which greatly limits the widespread use of neonicotinoids in agriculture.
With the rapid development of structure biology, molecular biology and bioinformatics, a new multidisciplinary cross Drug development method, Computer-aided Drug Design (CADD), was born and developed. CADD is based on molecular simulation technology and mathematical statistics, virtual screening and calculation are carried out, a platform is built for chemistry and biology, active compounds possibly acting on targets are searched in a database, the synthesis and bioassay range is narrowed, the time for developing new drugs is shortened, and the investment of manpower and financial resources is reduced, so that the new drug development efficiency is improved (Veselovsky, A.V.curr.drug targets Infect disease 2003,3, 33-40; Bailey, D.drug Discov.Today2001,6, 57-59).
Disclosure of Invention
The invention aims to provide a new application of sulfonamide compounds in the aspect of controlling agricultural pests.
The invention takes the structure of a nicotine acetylcholine receptor as the guide, adopts a pharmacophore and a receptor structure model to carry out virtual screening of a neonicotine functional compound with a novel structure, and screens out the sulfonamide compound shown as a formula I or a formula II.
Wherein R is1Represents hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 alkylthio, halogen, nitro, cyano, azido, hydroxyl or trifluoromethyl; r2Represents isopentenyl, C1-C10 alkyl, a phenyl ring, pyridine, thiazole, thiophene, pyrrole, furan, pyrazole, imidazole, pyran, pyrazine, pyrimidine, pyridazine, benzofuran, benzothiophene, indole, quinoline, trifluoromethyl or halogen.
The above sulfonamides can be purchased from commercial sources or synthesized by existing synthetic means.
The compound of formula I and formula II is used as active component to prepare pesticide for preventing and treating plant diseases and insect pests such as aphid.
The sulfonamides in the present invention act in a similar manner to neonicotinoids on targets, but exhibit different biological safety to non-targets than neonicotinoids. And the structure is simple, the modification space is large, and the pesticide can be used as a neonicotinoid aphid prevention and control agent with a novel structure.
Detailed Description
The present invention is further described below by way of specific examples, and it will be understood by those skilled in the art that the following examples are only for better understanding of the present invention and are not intended to limit the present invention in any way.
Two sulfonamides according to formula I and formula II, designated as VS03 and VS04, respectively, were purchased from beijing enokay science ltd, having the following structural formula:
the following test experiments were conducted by preparing liquid solutions having different concentrations using these compounds as the agricultural chemical active ingredients, respectively.
Aphid killing activity test experiment
Testing insects in an experiment: aphis glycines (Aphis glycines) is collected from a normal population raised indoors, and a medicament activity screening test is carried out by wingless adults with consistent age, weight and physiological conditions.
The experimental method comprises the following steps: soaking soybean leaves in a liquid medicine prepared by dimethyl sulfoxide by a leaf soaking method, inoculating wingless adults mainly with stomach toxicity and contact killing effects after the liquid medicine is dried, and respectively checking the death conditions of aphids for 24 hours and 48 hours. Concentration gradients were set at 500, 125, 31, 8 and 2 mg/L.
The death judgment standard is as follows: the insect body is touched, and six immotile individual pests are regarded as dead individual.
Bee toxicity test experiment
Testing insects in an experiment: adult italian worker bee (Apismellifera L.) supplied by the bee breeding base of the carnius carnea beijing. And selecting healthy and active adult worker bees with consistent sizes for testing.
The experimental method comprises the following steps: the test is carried out under the conditions of 25.0-25.2 ℃ of temperature, 56.8-58.6% of relative humidity and low light level. The concentration of 3 liquid medicines is set to be 1.10 multiplied by 10 respectively in the test4、2.75×103、6.875×102mg/L, and acetone is taken as an auxiliary agent. Before the test, the bees are anesthetized, then the liquid medicines with different concentrations are dripped on the middle chest back plate of the bees by the continuous distributor, and the bees are transferred to the recovery room for normal feeding after being completely recovered. Is divided intoThe 24h and 48h test results were recorded separately.
The death judgment standard is as follows: there was no response to touching the body of the bee.
The test results of the above experiments are shown in tables 1-2, and table 3 is a classification table of toxicity levels of pesticides to bees.
TABLE 1 Aphis citricola Activity of highly active compounds on Aphis fabae (Aphis glycines)
TABLE 2 acute contact toxicity of highly active compounds on bees
TABLE 3 rating of toxicity of pesticides to bees
As can be seen from the above test results, LC of compounds VS03 and VS0450The values are 29.55mg/L and 44.08mg/L respectively, have good aphidicidal activity and show low toxicity to non-target bees.
The above examples are merely illustrative of the invention, and other sulfonamides according to formula I and formula II also have similar properties to VS03 and VS04, due to the same sulfonamide groups as VS03 and VS 04.
The sulfonamides in the present invention act in a similar manner to neonicotinoids on targets, but exhibit different biological safety to non-targets than neonicotinoids. And the structure is different from neonicotinoid, the structure is simple, the modification space is large, and the neonicotinoid aphid control agent can be used as a neonicotinoid aphid control agent with a novel structure.
Claims (1)
1. The application of the sulfonamide compound in preventing and treating aphids is that the structural formula of the sulfonamide compound is as follows:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810768150.5A CN108617670B (en) | 2016-07-08 | 2016-07-08 | Application of sulfonamide compound in aphid prevention and control |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810768150.5A CN108617670B (en) | 2016-07-08 | 2016-07-08 | Application of sulfonamide compound in aphid prevention and control |
| CN201610535020.8A CN106172439B (en) | 2016-07-08 | 2016-07-08 | Application of the sulfonamides compound in terms of preventing agricultural pests |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| CN201610535020.8A Division CN106172439B (en) | 2016-07-08 | 2016-07-08 | Application of the sulfonamides compound in terms of preventing agricultural pests |
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| Publication Number | Publication Date |
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| CN108617670A CN108617670A (en) | 2018-10-09 |
| CN108617670B true CN108617670B (en) | 2020-05-15 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN201610535020.8A Active CN106172439B (en) | 2016-07-08 | 2016-07-08 | Application of the sulfonamides compound in terms of preventing agricultural pests |
| CN201810768150.5A Active CN108617670B (en) | 2016-07-08 | 2016-07-08 | Application of sulfonamide compound in aphid prevention and control |
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| CN201610535020.8A Active CN106172439B (en) | 2016-07-08 | 2016-07-08 | Application of the sulfonamides compound in terms of preventing agricultural pests |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CS269448B1 (en) * | 1988-10-20 | 1990-04-11 | Novacek Alois | Derivatives of sulphonamides |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ269396A3 (en) * | 1994-03-21 | 1996-12-11 | Bayer Ag | N-aryl- and n-alkylsulfonylaminals, process of their preparation and use for fighting pest |
| AR080684A1 (en) * | 2010-03-18 | 2012-05-02 | Bayer Cropscience Ag | ARIL- AND HETARILSULFONAMIDAS AS ACTIVE SUBSTANCES AGAINST AN ABIOTIC PLANTS STRESS |
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2016
- 2016-07-08 CN CN201610535020.8A patent/CN106172439B/en active Active
- 2016-07-08 CN CN201810768150.5A patent/CN108617670B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CS269448B1 (en) * | 1988-10-20 | 1990-04-11 | Novacek Alois | Derivatives of sulphonamides |
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| CN106172439A (en) | 2016-12-07 |
| CN106172439B (en) | 2018-08-17 |
| CN108617670A (en) | 2018-10-09 |
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