A toxic fluoride-phosphorus composition for controlling plant viral diseases

By combining cyhalothrin and (1S,3S)-N'-(4-chlorophenylmethylene)-1-methyl-2,3,4,9-tetrahydropyrido[3,4-b]indole-3-carboxylhydrazine, various formulations were prepared, solving the problem of single efficacy in existing technologies and achieving efficient control of plant viral diseases and promotion of crop growth.

CN112741104BActive Publication Date: 2026-03-10JINGBO AGROCHEM TECH CO LTD
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2021-01-14
Publication Date
2026-03-10

AI Technical Summary

Technical Problem

The existing technology lacks a technical solution to combine two substances with good efficacy, cyclophosphamide and (1S,3S)-N'-(4-chlorophenylmethylene)-1-methyl-2,3,4,9-tetrahydropyrido[3,4-b]indole-3-carboxylhydrazine, resulting in the limited scope of single-agent use and poor efficacy.

Method used

A composition containing toxic fluoride phosphate and (1S,3S)-N'-(4-chlorophenylmethylene)-1-methyl-2,3,4,9-tetrahydropyrido[3,4-b]indole-3-carboxylhydrazine is provided, with the effective ingredient ratio being 20%-45%. It is prepared into formulations such as aqueous solutions, soluble concentrates, suspensions, wettable powders, and water-dispersible granules. By activating photosynthesis and regulating endogenous plant growth factors, it promotes root growth, inhibits viral infection, and improves crop stress resistance.

Benefits of technology

It significantly improved the control effect of plant viral diseases, enhanced the drought and high temperature resistance of crops, promoted flowering and fruit yield, delayed the decline of control efficacy, expanded the scope of application of the agent, and improved crop growth and fruit quality.

✦ Generated by Eureka AI based on patent content.

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Abstract

This invention belongs to the field of pesticides and provides a composition containing toxic fluoride for the control of plant viral diseases. The composition uses toxic fluoride and (1S,3S)-N'-(4-chlorophenylmethylene)-1-methyl-2,3,4,9-tetrahydropyrido[3,4-b]indole-3-carboxylhydrazine as active ingredients, with the active ingredients accounting for 20%-45% of the total composition by weight. This composition can be used to control viral diseases in various plants, such as cucumbers, tobacco, celery, peppers, and potatoes. It can also improve crop resistance to drought and high temperatures, regulate crop growth, promote flowering, and increase fruit yield and quality.
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Description

TECHNICAL FIELD

[0001] The application belongs to the technical field of pesticides, and provides a virus disease control composition containing tolfenpyrad. BACKGROUND

[0002] Tolfenpyrad is a novel fluorine-containing amino phosphonate antiviral agent with the structure of (N-[2-(4-methylbenzothiazolyl)]-2-amino-2-fluorophenyl-O,O-diethyl phosphonate). Tolfenpyrad can activate the salicylic acid signaling pathway of tobacco, increase the content of signal molecules salicylic acid, and thus promote the expression of downstream disease-related proteins. Tolfenpyrad can also obtain antiviral ability by inducing the defense enzyme activities of tobacco PAL, POD and SOD. Tolfenpyrad can also reduce the invasion of viruses to hosts by aggregating TMV particles, and has the functions of improving the disease resistance of plants and promoting the growth of crops.

[0003] The structure of tolfenpyrad is as follows:

[0004]

[0005] The structure of (1S,3S)-N-(4-chlorophenylmethylidene)-1-methyl-2,3,4,9-tetrahydropyrido[3,4-b]indole-3-carbohydrazide is as follows:

[0006]

[0007] (1S,3S)-N'-(4-chlorophenylmethylidene)-1-methyl-2,3,4,9-tetrahydropyrido[3,4-b]indole-3-carbohydrazide has very good biological activity on tobacco mosaic virus, is easily absorbed by plants, is easily degraded in the environment, and has good environmental compatibility.

[0008] The prior art has technical solutions of using the two substances alone or in combination with other components, but lacks technical solutions of using the two substances in combination. There is no corresponding technical inspiration in the prior art. Therefore, how to combine the two substances with good efficacy has become one of the problems to be solved in the prior art. SUMMARY

[0009] The present application provides a virus disease control composition containing tolfenpyrad, which contains tolfenpyrad and (1S, 3S)-N'-(4-chlorophenylmethylene)-1-methyl-2, 3, 4, 9-tetrahydro pyrido [3, 4-b] indole-3-carbonyl hydrazine as effective components, and the weight percentage of the effective components in the total components is 20%-45%. The composition can be used for preventing and treating virus diseases of various plants such as cucumber, tobacco, celery, pepper and potato, and can improve the stress resistance of crops such as drought resistance and high temperature resistance, and can regulate crop growth, promote flowering, improve fruit yield and quality.

[0010] The specific technical solutions of the present application are as follows:

[0011] A virus disease control composition containing tolfenpyrad, which contains tolfenpyrad and (1S, 3S)-N'-(4-chlorophenylmethylene)-1-methyl-2, 3, 4, 9-tetrahydro pyrido [3, 4-b] indole-3-carbonyl hydrazine as active components, and the weight percentage of the active components in the total components is 20%-45%, wherein the weight percentage of tolfenpyrad in the compound composition is 10%-30%, and the weight percentage of (1S, 3S)-N'-(4-chlorophenylmethylene)-1-methyl-2, 3, 4, 9-tetrahydro pyrido [3, 4-b] indole-3-carbonyl hydrazine in the compound composition is 10%-15%; the weight ratio of tolfenpyrad and (1S, 3S)-N'-(4-chlorophenylmethylene)-1-methyl-2, 3, 4, 9-tetrahydro pyrido [3, 4-b] indole-3-carbonyl hydrazine is 1:8-5:1; and more preferably, the weight ratio of the two is 1:2-2:1;

[0012] After the two agents are combined in the above-mentioned ratio, the following beneficial effects can be obtained:

[0013] ① Activating photosynthesis to promote plant growth, and at the same time, promoting root growth, restoring leaf function and reducing yield loss by regulating plant endogenous growth factors;

[0014] ② Stimulating the increase of ethylene content to cause stress resistance;

[0015] ③ Interacting with virus coat protein to inhibit virus infection;

[0016] The above three effects exist simultaneously, which is of great significance to crop growth.

[0017] The above-mentioned composition can be directly prepared into various dosage forms, mainly any one of water, soluble liquid, soluble powder, suspension and water dispersible granule, and the specific preparation method is a conventional preparation method in the art, which will not be described here by the inventors.

[0018] The composition provided by the present application can effectively prevent and treat viral diseases of fruit trees, vegetables and field crops, and can improve the stress resistance of crops, promote the growth of crops and increase the yield. Compared with the prior art, the technical scheme of the present application expands the use range of toxaphene and (1S, 3S)-N'-(4-chlorophenylmethylene)-1-methyl-2, 3, 4, 9-tetrahydro pyrido [3, 4-b] indole-3-carbonyl hydrazine single agent, and the combination of toxaphene and (1S, 3S)-N'-(4-chlorophenylmethylene)-1-methyl-2, 3, 4, 9-tetrahydro pyrido [3, 4-b] indole-3-carbonyl hydrazine can effectively improve the efficacy of the single agent, regulate the growth of crops, promote flowering, increase fruit yield and quality, has obvious promoting effect on crop growth, and effectively delays the problem of poor prevention and treatment caused by single agent use. DETAILED DESCRIPTION

[0019] The above content of the present application is further described in detail through the specific embodiments in the form of examples, but this should not be understood as the scope of the above subject matter of the present application being limited to the following examples. Any technology achieved based on the above content of the present application belongs to the scope of the present application, and the following percentages are all weight percentages, and the adjuvants used are conventional adjuvants in the art.

[0020] Example 1

[0021] Preparation of 30% toxaphene·(1S, 3S)-N'-(4-chlorophenylmethylene)-1-methyl-2, 3, 4, 9-tetrahydro pyrido [3, 4-b] indole-3-carbonyl hydrazine aqueous agent

[0022] Raw material composition: 20% toxaphene, 10% (1S, 3S)-N'-(4-chlorophenylmethylene)-1-methyl-2, 3, 4, 9-tetrahydro pyrido [3, 4-b] indole-3-carbonyl hydrazine, 8% surfactant dodecylbenzenesulfonic acid, and deionized water to 100%. The above materials are uniformly mixed in a mixing agitator according to the corresponding proportion, and a 30% toxaphene·(1S, 3S)-N'-(4-chlorophenylmethylene)-1-methyl-2, 3, 4, 9-tetrahydro pyrido [3, 4-b] indole-3-carbonyl hydrazine aqueous agent is prepared.

[0023] Example 2

[0024] Preparation of 33% toxaphene·(1S, 3S)-N'-(4-chlorophenylmethylene)-1-methyl-2, 3, 4, 9-tetrahydro pyrido [3, 4-b] indole-3-carbonyl hydrazine soluble concentrate

[0025] Raw material composition: 22% of phosmet, 11% of (1S,3S)-N'-(4-chlorophenyl methylene)-1-methyl-2,3,4,9-tetrahydropyrido[3,4-b]indole-3-carbohydrazide, 2% of sodium dinitrate, 2% of ethylene glycol, 4% of crop oil 600#, 2% of cyclohexanone, cyclohexanone to 100%. The above materials are mixed uniformly in a mixing stirred tank according to the corresponding proportion, and a phosmet·(1S,3S)-N'-(4-chlorophenyl methylene)-1-methyl-2,3,4,9-tetrahydropyrido[3,4-b]indole-3-carbohydrazide soluble liquid with an active ingredient content of 33% is prepared.

[0026] Example 3

[0027] Preparation of 35% phosmet·(1S,3S)-N'-(4-chlorophenyl methylene)-1-methyl-2,3,4,9-tetrahydropyrido[3,4-b]indole-3-carbohydrazide wettable powder

[0028] Raw material composition: 20% of phosmet, 15% of (1S,3S)-N'-(4-chlorophenyl methylene)-1-methyl-2,3,4,9-tetrahydropyrido[3,4-b]indole-3-carbohydrazide, 8% of lignin sulfonate, 8% of alkyl sulfonate, 8% of citrate, diatomite to 100%. The above materials are mechanically pulverized and then air-pulverized, and mixed uniformly, and a phosmet·(1S,3S)-N'-(4-chlorophenyl methylene)-1-methyl-2,3,4,9-tetrahydropyrido[3,4-b]indole-3-carbohydrazide wettable powder with an active ingredient content of 35% is prepared.

[0029] Example 4

[0030] Preparation of 40% phosmet·(1S,3S)-N'-(4-chlorophenyl methylene)-1-methyl-2,3,4,9-tetrahydropyrido[3,4-b]indole-3-carbohydrazide wettable powder

[0031] Raw material composition: 30% of phosmet, 10% of (1S,3S)-N'-(4-chlorophenyl methylene)-1-methyl-2,3,4,9-tetrahydropyrido[3,4-b]indole-3-carbohydrazide, 8% of lignin sulfonate, 7% of alkyl sulfonate, 10% of citrate, diatomite to 100%. The above materials are mechanically pulverized and then air-pulverized, and mixed uniformly, and a phosmet·(1S,3S)-N'-(4-chlorophenyl methylene)-1-methyl-2,3,4,9-tetrahydropyrido[3,4-b]indole-3-carbohydrazide wettable powder with an active ingredient content of 40% is prepared.

[0032] Example 5

[0033] Preparation of 45% tolfenpyrad · (1S, 3S)-N'-(4-chlorophenyl methylene)-1-methyl-2, 3, 4, 9-tetrahydropyrido [3, 4-b] indole-3-carbohydrazide suspension

[0034] The raw material composition is: 30% tolfenpyrad, 15% (1S, 3S)-N'-(4-chlorophenyl methylene)-1-methyl-2, 3, 4, 9-tetrahydropyrido [3, 4-b] indole-3-carbohydrazide, 6% sodium lignosulfonate, 1.2% kaolin, 1% xanthan gum, 1% SAG622 silicone, 8% glycerol, 0.8% sodium tripolyphosphate, and the rest is made up with deionized water. The 45% tolfenpyrad · (1S, 3S)-N'-(4-chlorophenyl methylene)-1-methyl-2, 3, 4, 9-tetrahydropyrido [3, 4-b] indole-3-carbohydrazide suspension is prepared by conventional suspension production method.

[0035] Example 6

[0036] Preparation of 45% tolfenpyrad · (1S, 3S)-N'-(4-chlorophenyl methylene)-1-methyl-2, 3, 4, 9-tetrahydropyrido [3, 4-b] indole-3-carbohydrazide suspension

[0037] The raw material composition is: 30% tolfenpyrad, 15% (1S, 3S)-N'-(4-chlorophenyl methylene)-1-methyl-2, 3, 4, 9-tetrahydropyrido [3, 4-b] indole-3-carbohydrazide, 6% sodium lignosulfonate, 1.2% kaolin, 1% xanthan gum, 1% SAG622 silicone, 8% glycerol, 0.8% sodium tripolyphosphate, and the rest is made up with deionized water. The 45% tolfenpyrad · (1S, 3S)-N'-(4-chlorophenyl methylene)-1-methyl-2, 3, 4, 9-tetrahydropyrido [3, 4-b] indole-3-carbohydrazide suspension is prepared by conventional suspension production method.

[0038] Example 7

[0039] Preparation of 45% tolfenpyrad · (1S, 3S)-N'-(4-chlorophenyl methylene)-1-methyl-2, 3, 4, 9-tetrahydropyrido [3, 4-b] indole-3-carbohydrazide suspension

[0040] Raw material composition: 10% of toxaphene, 15% of (1S,3S)-N'-(4-chlorophenyl methylene)-1-methyl-2,3,4,9-tetrahydro-pyrido[3,4-b]indole-3-carbohydrazide, 10% of lignin sulfonate, 6% of alkyl sulfonate, 8% of glucose, 4% of corn starch, kaolin and white carbon black to 100%. The above materials are crushed by a super micro air flow crusher, kneaded, then added into a fluidized bed granulator dryer for granulation, drying and screening, thus obtaining a water dispersible granule of toxaphene·(1S,3S)-N'-(4-chlorophenyl methylene)-1-methyl-2,3,4,9-tetrahydro-pyrido[3,4-b]indole-3-carbohydrazide with an active ingredient content of 25%.

[0041] Example 8

[0042] Preparation of a water dispersible granule of 28% of toxaphene·(1S,3S)-N'-(4-chlorophenyl methylene)-1-methyl-2,3,4,9-tetrahydro-pyrido[3,4-b]indole-3-carbohydrazide

[0043] Raw material composition: 15% of toxaphene, 13% of (1S,3S)-N'-(4-chlorophenyl methylene)-1-methyl-2,3,4,9-tetrahydro-pyrido[3,4-b]indole-3-carbohydrazide, 6% of alkyl naphthalene sulfonate, 3% of naphthalene sulfonate, 4% of sucrose, 3% of corn starch, kaolin to 100%. The above materials are crushed by a super micro air flow crusher, kneaded, then added into a fluidized bed granulator dryer for granulation, drying and screening, thus obtaining a water dispersible granule of toxaphene·(1S,3S)-N'-(4-chlorophenyl methylene)-1-methyl-2,3,4,9-tetrahydro-pyrido[3,4-b]indole-3-carbohydrazide with an active ingredient content of 38%.

[0044] Experimental example

[0045] In order to verify the prevention and treatment effect of the present application on viral diseases, field prevention and treatment verification was carried out on cucumber viral diseases respectively, and the verification results are as follows:

[0046] Field test experiment: field efficacy test of the combination of tolfenpyrad and (1S,3S)-N'-(4-chlorophenylmethylidene)-1-methyl-2,3,4,9-tetrahydropyrido[3,4-b]indole-3-carbohydrazide on cucumber virus disease Field determination: after the combination of different contents of (1S,3S)-N'-(4-chlorophenylmethylidene)-1-methyl-2,3,4,9-tetrahydropyrido[3,4-b]indole-3-carbohydrazide and tolfenpyrad was compounded into 8 different formulations, leaf spraying was carried out at the early stage of cucumber virus disease, and the use amount of each treatment per mu was 6 ml for examples 1 and 2; 7.5 g for example 3; 6 g for example 4; 5 g for example 5; 7.5 g for examples 6, 7 and 8; 15 L of water per mu, and the control agent was 30% tolfenpyrad wettable powder with a single agent use amount of 15 g, 10% (1S,3S)-N'-(4-chlorophenylmethylidene)-1-methyl-2,3,4,9-tetrahydropyrido[3,4-b]indole-3-carbohydrazide with a single agent use amount of 15 g, and 0.5% amino oligosaccharide water agent with a use amount of 20 g, which were respectively diluted with 15 L of water; the first spraying was carried out at the early stage of cucumber virus disease, and a total of three times of spraying were carried out with an interval of 7 days, and the investigation was carried out 7 days and 14 days after the three times of spraying, respectively, the disease index was classified according to the relevant data, the disease index was calculated, and the results are shown in Table 1.

[0047] The classification standard is as follows:

[0048] 0 level: no disease;

[0049] 1 level: the area of disease spot pile accounts for less than 8% of the whole leaf area;

[0050] 3 level: the area of disease spot pile accounts for less than 6%-10% of the whole leaf area;

[0051] 5 level: the area of disease spot pile accounts for less than 11%-20% of the whole leaf area;

[0052] 7 level: the area of disease spot pile accounts for less than 21%-80% of the whole leaf area;

[0053] 9 level: the area of disease spot pile accounts for more than 80% of the whole leaf area.

[0054] The calculation method of the efficacy is as follows:

[0055] Disease leaf rate (%) = number of diseased leaves / total number of investigated leaves × 100

[0056] Disease index = Σ (number of leaves at each level × relative level value) / (total number of investigated leaves × 9) × 100

[0057] Control effect (%) = [1- (disease index of blank control area before treatment × disease index of treatment area after treatment) / (disease index of blank control area after treatment × disease index of treatment area before treatment)] × 100.

[0058] Table 1 prevention effect of different agents on cucumber virus disease

[0059]

[0060] The above field test shows that the prevention effect of each mixture of tolfenpyrad and (1S, 3S)-N'-(cyclohexylmethyl)-1-methyl-2, 3, 4, 9-tetrahydro-pyrido [3, 4-b] indole-3-carbohydrazide on cucumber virus disease is obviously higher than that of tolfenpyrad, (1S, 3S)-N'-(cyclohexylmethyl)-1-methyl-2, 3, 4, 9-tetrahydro-pyrido [3, 4-b] indole-3-carbohydrazide and amino oligosaccharide, and the prevention effect is higher than 51% after 14 days after application, and the effective period is obviously prolonged.

[0061] Yield determination

[0062] According to the prevention effect comparison between different treatments in the early stage in Table 1, whether the different treatments have certain influence on the yield of cucumber under the same method and same amount in Table 1 is verified in the later stage, the fruits without any diseases and pests are picked batch by batch in the cucumber fruit picking period, weighed, the yield of each test area is counted, and the yield increase rate is calculated: yield increase rate=(treatment area yield-control area yield) / control area yield*100%.

[0063] Table 2 influence of different agent treatments on cucumber yield

[0064]

[0065] As shown in Table 2, the different agent treatments of the application on cucumber have a certain degree of yield increasing effect, the yield increase is between 8848-27618 kg / hm 2 compared with the blank control, which has a significant yield increasing effect, and the yield increase rate of the two agent combinations is obviously higher than that of tolfenpyrad, (1S, 3S)-N'-(cyclohexylmethyl)-1-methyl-2, 3, 4, 9-tetrahydro-pyrido [3, 4-b] indole-3-carbohydrazide and amino oligosaccharide. The use of two agent combinations can obviously regulate crop growth, promote flowering, improve fruit yield and quality, the cucumber growth and development in each test area is normal, and no any adverse effect is found, which proves that the test agents are safe, and have high popularization and application value.

Claims

1. A composition for plant yield enhancement, characterized by: The main active ingredient of the composition is tolufenspiron and (1S, 3S)-N'-(4-chlorophenyl methylene)-1-methyl-2, 3, 4, 9-tetrahydro pyridine [3, 4-b] indole-3-methyl hydrazine, the total weight percentage of the active ingredient is 35%-45%, and the weight ratio of tolufenspiron and (1S, 3S)-N'-(4-chlorophenyl methylene)-1-methyl-2, 3, 4, 9-tetrahydro pyridine [3, 4-b] indole-3-methyl hydrazine is 4:3-3:

1. The dosage form of the composition is any one of soluble liquid, soluble powder, suspension, and water dispersible granule.

Citation Information

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