JPS6141484B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a plant virus disease control agent, and more specifically, to a drug having the effect of preventing infection of plants such as tobacco, tomatoes, green peppers, cucumbers, and watermelons by Ayurus. Tomatoes, peppers, cowpeas, green beans, cucumbers, watermelons, etc. grown in fields or in various facilities such as greenhouses are infected with Tobacco Mosaic Virus (TMV).
), cucumber mosaic virus (hereinafter referred to as
CMV) and cucumber green spot mosaic virus (hereinafter abbreviated as CGMMV), which are caused by plant viruses such as mosaic disease and wilt disease, which often cause enormous damage. These plant viruses exist in other crops, weeds, seeds, soil, residual roots in the soil, etc., and are caused by insect suction, human contact (e.g. contact with agricultural machinery, human hands or clothing), or transplantation or planting. It is transmitted to crops through contact with the soil, etc., and once a primary infection is established, there is a high risk that it will spread throughout the field or facility through human contact such as agricultural work. Conventional agents used to control plant virus diseases include antibiotics and nucleobase analogues that have the effect of suppressing the proliferation of plant viruses, or pokeweed, pigweed, carnation, etc. that have the effect of inhibiting the infection of plant viruses to crops. Plant sap and biopolymer substances such as casein and alginic acid are known. However, the former is toxic to both crops and human stock, so none has been put into practical use, and the latter is derived from natural products, so it is difficult to mass-produce products with uniform ingredients. However, only a few products containing sodium alginate as the main component have been put into practical use. (Alginic acid hydrating agent: Ministry of Agriculture, Forestry and Forestry Registration No. 13440) Therefore, once a disease occurs in crop cultivation sites, a passive method is taken to remove the diseased plant as soon as it is found and burn it to prevent secondary infection from the diseased plant. This is the actual situation. The present inventors conducted intensive studies to develop safe and highly effective plant virus disease control agents, and as a result, they discovered that (3-chloro-2-hydroxy)propypyl diallylamine hydrochloride and dimethyl diallylammonium chloride. The inventors have discovered that a cyclized polymer obtained by copolymerization has high plant virus disease control activity, and have arrived at the present invention. Next, the present invention will be explained in detail. The polymers used in the present invention are (3-chloro-2-hydroxy)propyl diallylamine hydrochloride (hereinafter referred to as a compound) represented by the following general formula () and dimethyldiallylammonium chloride represented by the following general formula (). (hereinafter referred to as a compound). The copolymerization reaction involves water, dimethyl sulfoxide,
It is carried out using a solvent such as dimethylformamide, methyl alcohol, ethyl alcohol, dimethylacetamide, etc. at a temperature in the range of 0 to 80°C. Further, as the catalyst, radical catalysts such as ammonium persulfate, potassium persulfate, azobisisobutyronitrile, tert-butyl hydroperoxide, and cumene hydroperoxide are used. Regarding the method and conditions of the copolymerization reaction, please refer to
14326, Japanese Patent Publication No. 45-1457, Japanese Patent Publication No. 47-17918, Japanese Patent Publication No. 46-443, etc. Although the molar ratio of the compounds to be charged in the reaction can be arbitrarily determined, the molar ratio of (compound)/(compound) is preferably selected within the range of 0.05 to 10. The polymer obtained by the above copolymerization reaction has a structural unit represented by the following general formula (). In the general formula (), a is a numerical value determined by the reaction charge molar ratio of compound () and compound () and other reaction conditions, and is in the range of 0<a<1. Regarding the viscosity of the polymer, in consideration of ease of handling during drug use and biological activity, the rotational viscosity of an aqueous solution diluted to 2% by weight is 1.5 to 30 cps,
In particular, it is preferable to set it in a range of 2.0 to 20 cps. In the present invention, the above polymer can be used alone as a plant virus disease control agent, but it can be used in the form of a wettable powder, emulsion, or liquid by adding an inert solvent, surfactant, etc. as an adjuvant. May be used. When used as a wettable powder, a surfactant is used to improve the dispersibility of the drug when added to water and to increase the spreading effect when sprayed on plants. The surfactant can be selected from a wide range of general nonionic and cationic surfactants, such as polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether sulfate, polyoxyethylene sorbitan monolaurate, etc. It will be done. These surfactants can be used in combination of two or more, if necessary. On the other hand, when used as an emulsion or liquid, in addition to adjuvants, water or solvents that easily mix with water, such as alcohols such as methyl alcohol, ethyl alcohol, and ethylene glycol, ketones such as acetone, dioxane, THF, etc. One or a mixture of two or more of solvents such as ethers, amides such as dimethylformamide, etc. are used. When applying the plant virus disease control agent of the present invention in the form of a wettable powder, 70 to 99 parts of the active ingredient polymer,
1 to 30 parts of a surfactant are mixed in an appropriate ratio and diluted with water to a predetermined concentration before application. When applied in the form of an emulsion or solution, 10 to 60 parts of the active ingredient polymer, 20 to 90 parts of the solvent, and 1 to 20 parts of the surfactant.
Mix the parts in appropriate proportions, dilute with water and apply as in the case of wettable powders. The plant virus disease control agent of the present invention can be used in soil treatment or by spraying on growing crops.
It effectively controls the infection of viruses such as TMV, CMV, and CGMMV, but its application method is as a wettable powder, emulsion, or liquid, depending on the concentration of the active ingredient.
50-500l of 500-5000ppm solution per 10 ares
Use by spraying on leaves or by irrigating the soil. Furthermore, the pesticidal agent of the present invention can be used in combination with other active ingredients that do not inhibit the antiviral activity of the active ingredient, such as bactericides, insecticides, acaricides, etc. Next, the present invention will be explained in more detail with reference to production examples of polymers that are the active ingredients of the pest control agent of the present invention and test examples using drugs containing these polymers as active ingredients. You are not limited to the following examples as long as they do not exceed. Note that the compound numbers in the test examples correspond to the compound numbers described in the production examples. Production example 1 Dimethyldiallylammonium chloride
9 g of (3-chloro-2-hydroxy)propyl diallylamine hydrochloride and 10 g of dimethyl sulfoxide were placed in a test tube, and 210 mg of ammonium persulfate was added as a polymerization catalyst. After degassing the inside of the tube, the tube was replaced with nitrogen gas. Thereafter, the tube was sealed and allowed to stand for 24 hours to polymerize in a constant temperature bath at 50°C. After polymerization, the sealed tube was opened, a small amount of methanol was added to the solidified polymer to dissolve it, and the resulting viscous liquid was added to a large amount of acetone to precipitate a gel. Next, the precipitated gel was separated, washed with acetone, and then dried under reduced pressure to obtain 6.9 g of the desired polymer (Compound No. 1). The rotational viscosity of this polymer is shown in Table 1. Incidentally, the rotational viscosity is a value measured using a 2% by weight aqueous solution of the polymer at 20° C. using a Vismetron VSA-L rotational viscometer manufactured by Shibaura System Co., Ltd. Production example 2 7.5g of dimethyldiallylammonium chloride
1.25 g of (3-chloro-2-hydroxy)propyldiallylamine hydrochloride and 3.75 g of water were placed in a test tube, and ammonium persulfate was added as a polymerization catalyst.
After adding 180 mg, the inside of the tube was degassed and replaced with nitrogen gas, the tube was sealed, and polymerization was allowed to stand for 24 hours in a constant temperature bath at 45°C. The viscous solution obtained after polymerization was added to a large amount of acetone to precipitate a white polymer. Next, this precipitate was filtered off and dried at 45°C under reduced pressure to obtain 5.5 g of a polymer (compound No. 2). The intrinsic viscosity of this polymer was measured using an Ubbelohde viscometer and was found to be 0.1N.
It was 0.407 at 25℃ in saline solution. Production Example 3 The reaction was carried out in the same manner as in Production Example 2, except that the polymerization temperature was changed to 60°C, to obtain the desired polymer (Compound No. 3). The intrinsic viscosity of the polymer in 0.1N saline solution at 25℃ is
It was 0.375. Production Example 4 In Production Example 2, the polymerization temperature was 60℃ and the amount of water was
The reaction was carried out in the same manner as in Production Example 2, except that the amount of ammonium persulfate added was changed to 210 mg, and the desired polymer (compound part No. 4) was obtained. The intrinsic viscosity of this polymer in 0.1N saline solution at 25℃ is
It was 0.175. Production Example 5 Same as Production Example 2 except that the amount of dimethyldiallylammonium chloride was 6.4g and the amount of (3-chloro-2-hydroxy)propyldiallylamine hydrochloride was 1.6g. A similar reaction was carried out to obtain the desired polymer (Compound No. 5). Similarly, the amount of dimethyldiallylammonium chloride charged was 5g, the amount of (3-chloro-2-hydroxy)propyldiallylamine hydrochloride was charged 5g, and the amount of water charged was 4.3g, and polymerization was carried out to obtain a polymer (Compound No. 6 ) was obtained. Similarly, the amount of dimethylallylammonium chloride charged was 3g, and the amount of (3-chloro-2-hydroxy)propyldiallylamine hydrochloride was changed to 3g.
7 g, and the amount of water charged was 4.2 g to obtain a polymer (Compound No. 7). Furthermore, in the same manner, the amount of dimethyldiallylammonium chloride charged was 1 g, (3-chloro-2
-Hydroxy) propyl diallylamine hydrochloride was charged in an amount of 9 g, water was added in an amount of 4.3 g, and polymerized.
A polymer (compound No. 8) was obtained. Test Example 1 Potted tobacco seedlings of Xanthi nc (10 to 11 leaf ages) were treated with the compounds shown in Table 1.
2000ppm, 1000ppm aqueous solution per cigarette
Spray 50ml with a spray gun, air dry, then contact with separately prepared TMV purified liquid (5 x 10 ^-7 g/ml) using the conventional carborundum method, leave in a greenhouse for 3 to 4 days, and apply locally. Local lesions
lesions) were formed. The investigation involved checking the number of local lesions formed and comparing them with those in the untreated area.
The TMV lesion formation inhibition rate was determined. The TMV purified solution was prepared by separating and purifying the sap of TMV-infected leaves using an ultracentrifuge. The results are shown in Table 1. In addition, when tobacco seedlings (Bright Yellow) were sprayed with the compounds shown in Table 1 at a concentration of 2000 ppm and their chemical damage was investigated, no atrophy or drug spots were observed in the seedlings.

[Table] 〓 Treatment area〓
TMV lesion shape

Claims (1)

[Claims] 1. A plant virus disease control agent containing as an active ingredient a polymer obtained by copolymerizing (3-chloro-2-hydroxy)propyldiallylamine hydrochloride and dimethyldiallylammonium chloride.