JPS606327B2 - Improved plant disease control agent - Google Patents

Description

[Detailed description of the invention] The present invention relates to an improved plant disease control agent.

N. N-bis[(1-formamido-2,2,2-trichloro)ethyl]piverazine (hereinafter abbreviated as "triforine") is a relatively low-toxic piperazine fungicide, and its 15% emulsion is effective against a wide range of plant diseases, especially It has shown excellent control effects against powdery mildew, rust, scab, scab, and anthracnose, which are important diseases of vegetables, fruit trees, and flowering plants that have been widely cultivated in recent years. However, this triforine emulsion
It has the disadvantage of poor stability during storage and reduced potency.
Furthermore, even if a hydrating powder is prepared by micronizing triforine using a known method, the essential control effect is inferior, and furthermore, if this drug is diluted with water to prepare a spray solution, crystals will precipitate, leading to a deterioration of the medicinal efficacy. At times, the spray nozzle opening was closed, making spraying difficult.

In view of the above circumstances, the present inventors have conducted various studies and found that an alkali metal salt of alkylnaphthalene sulfonate having surface activity exhibits a specific stabilizing effect on triforine, and at the same time serves as a drug efficacy improver and crystal precipitation preventive agent. The present invention was completed based on the discovery that it exhibits outstanding effects as a drug.

That is, the present invention relates to a plant control agent containing triforine and an alkylnaphthalene sulfonic acid alkali metal salt.

The alkylnaphthalene sulfonic acid alkali metal salt used in the present invention is an alkali metal salt of a compound in which one or more alkyl groups and one or more sulfonic acid groups are directly substituted on the naphthalene nucleus.

Examples of alkyl groups here include methyl, ethyl, etc.
Propyl, butyl, bentyl, hexyl, hebutyl, octyl, etc. having 1 to 8 carbon atoms are used, and 1 to 2 of the same or different alkyl groups are substituted. If so, it is preferably a mono-substituted product or a di-substituted product with a lower alkyl group having 1 to 4 carbon atoms. The sulfonic acid group substituted on the naphthalene nucleus is
Although one may be sufficient, it may be desirable to substitute two or three. As the alkali metal, for example, sodium lithium, potassium, etc. are frequently used. Although such alkylnaphthalene sulfonic acid alkali metal salts are usually commercially available products and contain several tens of percent of a solvent such as ethylene glycol, this is not a problem for the purpose of the present invention. However, it is best to remove impurities such as sulfur as much as possible. Such an alkylnaphthalene sulfonic acid alkali metal salt can be prepared by a method known per se, for example, "Synthesis and Application of Surfactants", pp. 88-90, 1957 (published by Yoko Shoten), USP.
2020358USP. 2143493 etc.

When preparing a triforine emulsion, the alkylnaphthalene sulfonic acid alkali metal salt should be 0.3 to triforine.
It is better to borrow ~1 times, preferably 0.5 to 0.7,
In addition, it is good to use a solvent such as N-methylpyrrolidone or dimethylformamide in an amount of 1 to 4 times, preferably 2 to 3 times.

In addition, when producing a triforine hydrating powder, use 31 to 4 times, preferably 2 to 3 times as much as triforine, and add 3 to 1 times as much mineral powder as described below, preferably 5 to 3 times the amount of triforine.
It is better to mix 8 times. The present invention is capable of exhibiting excellent functions and effects for the first time as a result of implementing the above-mentioned constituent elements in close combination.
Triforine preparations such as the present invention are completely unknown outside of Japan.

Although the mechanism of action of the present invention is unknown, it can always be repeatedly used to exhibit excellent actions and effects.
4 In addition, as a result of various studies, the triforine preparation of the present invention contains nonionic and anionic surfactants such as commonly used polyoxyalkylaryl ethers and alkylaryl sulfonates in addition to the alkylnaphthalene sulfonate according to the present invention. It is also possible to mix and use them together. The fine mineral powder used in the hydrating agent of triforine includes, for example, diatoms such as Kunilite (trade name, Kunimine Kako Manufacturing Co., Ltd.), radiolite, and Siekrite (trade name, Sickle Chemical Industry Manufacturing Co., Ltd.). Kaolins and other microorganisms such as VitaSeal (product name, Takihijo Manufactured by Tokuyama Soda Manufacturing Co., Ltd.), NipSeal (product name, Nippon Silica Manufacturing Co., Ltd.), and Carbrex (product name, Shionogi Pharmaceutical Co., Ltd.) Powdered citric acid, clays such as zeolite (trade name, manufactured by Sun. Zeolite), clays such as kaolin, bentonite, acid clay, and talcs such as jadeite powder and waxite powder are used. The seed or a mixture of two or more types can be used.The particle size of the mineral powder is generally 200 mesh or more, preferably 300 mesh or more.The improved plant disease control agent of the present invention has the following properties: Triforine can usually be used after being diluted to a concentration of 50 to 20 ml, and its titer does not decrease much during storage, and it is stable for a long period of time even after dilution.

The method and effects of the present invention will be explained in detail below with reference to Examples.

Note that all parts and % in the examples indicate parts by weight and % by weight. Example 1 20 parts of triforine, 1 part of Alkanol-B (manufactured by Dupon, main component: sodium propylnaphthalene sulfonate), 3 parts of N-methylpyrrolidone, and 3 parts of dimethylformamide (hereinafter It is abbreviated as DMF.

) 4 emulsion obtained by adding the base and uniformly dissolving it. Example 2 An emulsion obtained by adding 65 parts of DMF to 20 parts of triforine and 15 parts of New Calgen Bx8oo (manufactured by Takemoto Yushi Co., Ltd., main component: sodium dibutylnaphthalene sulfonate) and uniformly dissolving the mixture.

Example 3 Triforin 2 base part'Konu Calgen B x 80pi ■7.
An emulsion obtained by adding 5 parts of N-methylpyrrolidone and 72.5 parts of N-methylpyrrolidone and uniformly dissolving the mixture.

Example 4 Potassium dibutylnaphthalene sulfonate (“Synthesis and Application of Surfactants” published by Yoko Shoten (1)
957), p. 90, 4-1;

) An emulsion obtained by adding and uniformly dissolving 1 Ikarito and 7 parts of N-methylpyrrolidone. Example 5 Triforine 20
NekaIA (Ai, G, (
1. An emulsion obtained by adding and homogeneously dissolving 2 parts of sodium butylpropylnaphthalene sulfonate and 60 parts of DMF.

Z example 6
Triforin 1 was synthesized by adding anhydrous hexanol to the reaction described in "Synthesis and Application of Sodium Butylhexylnaphthalene Sulfonate Surfactant" published by Enoki Shoten (1957), p. 90, 4-1.

) 15 parts of Z, 50 parts of DMF and 25 parts of xylene were added and uniformly dissolved to obtain an emulsion. Example 7 After uniformly mixing 1 part of triforine, 3 parts of alkanol, and 1 part of N-methylpyrrolidone, 77 parts of radiolite was added as a fine powder of mineral substance 2. After uniformly mixing with a drum blender, the mixture was further mixed with a hammer. A hydrating agent obtained by processing with a mold crusher.

Example 8 Triforine 1, Potassium dibutylnaphthalene sulfonate (Synthesis of Surfactants and Their Applications, published by Ichibun Shoten, 90)
It was synthesized according to the method described on pages 4-1.

Example 7) After uniformly mixing 1 base part and 5 parts of N-methylpyrrolidone, Toxil 2 Ikarito and 55 parts of clay were added.
Hydrated 3 Qi U obtained by uniformly mixing with the same machine. Example 9 After uniformly mixing 7.5 parts of triforine, 3 parts of Nucalgen Bx8oo, and 5 parts of sodium butylnaphthalene sulfonate, zeolite 6 Yuito and 324.5 parts of clay were added and mixed uniformly in the same manner as in Example 7. A hydrating agent obtained by

Example 10 Synthesis of a surfactant using 15 parts of triforine and sodium butylhexylnaphthalene sulfonate and its application 4, published by Yokoshoten (1957), p. 90, 4-1, by adding anhydrous hexanol to the method described in the Agency. did.

] After uniformly mixing 7 parts of N-methylpyrrolidone and 1 part of Togeto, 15 parts of Tokusil, 3 parts of Radiolite, and 2 parts of Chikaraolin were added and mixed uniformly in the same manner as in Example 7. . Example 11 After uniformly mixing 5 parts of triforine, 5 parts of Necal ■, and 5 parts of N-methylpyrrolidone, 2 parts of Radiolyte and 65 parts of clay were added and mixed uniformly in the same manner as in Example 7. Hydration obtained agent.

Experimental Example 1 (Stability test of triforine emulsion) The triforine emulsion according to the present invention shown in Examples 1 to 6 was placed in a sample bottle, stored in a 40°C incubator and at room temperature, and then subjected to high performance liquid chromatography (filling material: porous polystyrene). The amount of triforine was measured using gel) and the daily change was measured.

Table-1 ■ Control triforine emulsion Triforine 18.8 parts, tridecyl alcohol 5 parts,
A control triforine emulsion containing 18.8% trifoline obtained by homogeneously mixing and dissolving isopropylamine dodecylbenzenesulfonate 3 base, 26 parts dimethylformamide and 20.2 parts N-methylpyrrolidone.

Experimental Example 2 (Stability test of triforine hydrating agent) The triforine hydrating agent according to the present invention shown in Examples 6 to 11 was placed in a sample bottle and stored at room temperature in a 40°C incubator, and then subjected to high performance liquid chromatography ( The triforine content was measured using a filler (porous polystyrene gel), and changes over time were measured.

Table 2 ① Control triforine hydrating powder A hydrating powder obtained by adding 25 parts of the control trifoline emulsion, Toxil 4 Ikarigun and 35 parts of clay, mixing uniformly with a drum blender, and then processing with a hammer-type disintegrator.

Experimental Example 3 (Crystal precipitation test of triforine emulsion) The triforine emulsion according to the present invention shown in Examples 1 to 6 was
o Triforine was diluted with hard water and prepared in a total of 100 units, stored in a 30qo constant temperature chamber, and checked for crystal precipitation and whether or not the nozzle opening was closed during spraying.

Table-3

Claims (1)

[Claims] 1 N.N-bis[(1-formamide-2.2.2-
A plant disease control agent characterized by containing trichloroethyl]piperazine and an alkylnaphthalene sulfonic acid alkali metal salt.