JPS6135965B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a method for treating fungal infections of cultivated plants, particularly cereals and gourds, novel fungicidal compositions useful for the treatment thereof, fungicidal formulations containing the novel compositions, and fungicidal formulations thereof. Concerning methods of manufacturing things. Many plants of economic and ornamental importance are damaged every year by various types of mold. Because of the economic losses associated therewith, a great deal of research has been conducted in an attempt to discover methods and materials to control such harmful molds. U.S. Pat. No. 3,887,708 discloses various α・α-disubstituted-5-pyrimidinemethanes and methanols [α-(2-chlorophenyl)-α-(4-chlorophenyl)-5] as plant fungicides. -pyrimidinemethanol and α-(2-chlorophenyl)-α-(4-fluorophenyl)-5-pyrimidinemethanol].
2,4,5,6-tetrachloro-1,3-dicyanobenzene, known as tetrachloroisophthalonitrile and also known as chlorothalonil, is an effective plant fungicide. is US Patent No.
It is described in the specifications of No. 3290355 and No. 3331735. In particular, it has now been discovered that a surprising synergistic effect is achieved in the treatment of fungal infections in cultivated plants when using any of the pyrimidine methanols mentioned above in combination with 2,4,5,6-tetrachloro-1,3-dicyanobenzene. Discovered in the present invention. Therefore, according to the present invention, 2,4,5,6-tetrachloro-1,3-dicyanobenzene and the general formula () A fungicidal composition with a pyrimidine methanol having the formula (wherein X is chlorine or fluorine) is provided. 2,4,5,6-tetrachloro-1,3-dicyanobenzene (hereinafter abbreviated as "DCB") can be produced by the method described in US Pat. No. 3,290,353 or US Pat. No. 3,331,735 and has the general formula Pyrimidine methanol () can be produced by the method described in British Patent No. 1218632. The novel compositions of the present invention are surprisingly effective in controlling or resisting fungal infections such as mildew and septoria in cultivated plants, especially cereal crops and gourds. . In particular, the composition is compatible with the following plant pathogens: Erysiphe graminus, Septoria nodorum, Puccinia recondita, Fusarium nivale, Puccinia gramarum and Pseudoperonospora cubensis
It is particularly active against A. cubensis). Therefore, the present invention also relates to 2,4,5,6-tetrachloro-1,3-dicyanobenzene and general formula () (wherein X is chlorine or fluorine) and pyrimidine methanol is applied to the cultivated plants after fruiting and before harvest. The frequency and duration of this treatment will be determined by the actual or anticipated severity of the mold infection. Each component of the composition may be applied to the crop to be treated sequentially or simultaneously. Pyrimidine methanol is preferably 5 to 100 g/
hectare, advantageously applied in amounts of 20 to 100 g/ha, while DCB is preferably applied in amounts of 60 to 2000 g/ha.
It is applied advantageously in amounts of 500 to 2000 g/ha. Therefore, a suitable weight ratio of pyrimidine methanol to DCB is 1:400~
It is within the range of 1.6:1. It has been found that a particularly advantageous weight ratio of pyrimidine methanol to DCB in the treatment of fungal infections such as Puccinia recondeita in cereal crops is in the range 1:10 to 1.6:1. It has been found that a particularly advantageous weight ratio of pyrimidine methanol to DCB in the treatment of fungal infections such as P. cubensis in gourd is in the range 1:400 to 1:20. The novel compositions of the invention are advantageously used in the form of fungicidal formulations consisting of DCB and pyrimidine methanol of the above-mentioned general formula () in combination with an inert carrier harmless to plants. Such fungicidal formulations are also provided by the present invention. The present invention further encompasses a process for producing a fungicidal formulation comprising combining DCB and a pyrimidine methanol of general formula () as described above with an inert carrier that is harmless to plants. The combination of DCB and any of the pyrimidine methanols of the above general formula () is effective against wheat leaf rust caused by Psinia recondata and
It was found to have a synergistic effect in suppressing downy powdery mildew caused by P. cubensis. Pyrimidine methanol of the above general formula () and
In order to determine that the fungicidal effect obtained in combination with DCB was synergistic compared to the mildew control rate obtained by applying these two substances alone, SR Colby was tested. A developed formula (Weed, No. 15, pp. 20-22, 1967) was used.
As is well known to researchers in the field of plant science, the values obtained using the Colby equation, in this case the suppression obtained by the use of a combination of DCB and a pyrimidine methanol of the above general formula () If it is less than or equal to 1%, it is considered that a synergistic effect has occurred between the two active ingredients in their effects on mold. The fungicides of the present invention preferably consist of 5 to 90% by weight of active ingredient and will usually be in the form of a wettable powder or dust or an aqueous suspension. Wettable powders or fine powders consist of an intimate admixture of the active ingredient, one or more inert carriers and suitable surfactants. The inert carrier may be selected from attapulgite clays, montmorillonite clays, diatomaceous earth, kaolin, mica, talc and refined silicates. Effective surfactants include sulfonated lignin, naphthalene sulfonates and condensed naphthalene sulfonates, alkyl succinates,
It may be selected from nonionic surfactants such as alkylbenzene sulfonates, alkyl sulfates, and ethylene oxide adducts of phenols. An example of a wettable powder within the scope of the invention is one having the following composition. Wetting properties Powder wt% pyrimidine methanol 0.25-10 DCB 25-80 Surfactant 0-10 Dispersant 0-10 Anti-caking agent 0-10 Inert carrier Up to total 100 Aqueous suspensions are suitable surfactants, It consists of active ingredients suspended in water together with thickeners, antifreeze agents or preservatives. Suitable surfactants may be selected from those mentioned above for wettable powders.
Thickeners, when used, are usually selected from suitable cellulosic materials and natural gums, and glycols are generally used when antifreeze agents are required. Preservatives may be selected from a wide range of substances such as various paraben fungicides, phenols, O-chlorcresol, phenylmercury nitrate and formaldehyde. Examples of aqueous suspensions falling within the scope of the present invention have the following composition: Aqueous Suspension (Flowability) Weight % Pyrimidine Methanol 0.2-8 DCB 20-60 Surfactant 0-15 Viscous Agent 0-3 Freezing Inhibitor: 0-20 Preservative: 0-1 Anti-foaming agent: 0-0.5 Water Up to a total of 100 The above general examples will adequately illustrate to those skilled in the art the type of concentrated composition used in the present invention. However, the following non-limiting examples are presented to further illustrate the invention. In these examples
CCPM is the compound α-(2-chlorophenyl)-α-
(4-Chlorphenyl)-5-pyrimidinemethinol, and CFPM represents the compound α-(2-chlorophenyl)-α-(4-fluorophenyl)-5-pyrimidinemethanol. Examples 1 and 2 show specific examples of wettable powders according to the invention, Examples 3 and 4
relates to aqueous suspensions. EXAMPLE 1 CFPM 2 DCB 60 Ethoxylated Nonylphenol 4 Sodium Lignosulfonate 3 Silica 6 Kaolin 25 The active ingredients CFPM and DCB are ground and combined with the other ingredients in a conventional mixing device. This blend was then milled in a fluid energy mill with 1 to 10
The particle size is in the micron range and finally the mixture is recompounded and degassed prior to packaging. Similarly, the following concentrates were prepared: Example 2 CCPM 2.5 DCB 50 Sodium alkyl succinate 3 Sodium ligninsulfonate 3 Talc 41.5 Example 3 % by weight CFPM 2 DCB 50 Sodium naphthalene sulfonate 3 Gum arabic 1 Propylene glycol 10 O-chlor Cresol 0.3 Water Up to Total Volume 100 Both active ingredients, reduced in particle size by conventional methods if necessary, are dispersed in water containing a surfactant system, preservatives and some thickeners. The particle size of both components is further reduced by liquid milling, the remainder of the thickener is added and hydrated, and the product is diluted to volume with water. The following aqueous suspensions were prepared in the same way: Example 4 % by weight CCPM 1 DCB 50 Ethoxylated nonylphenol 2.0 Xanthan gum 0.2 Emulsion silicone
0.1 Water Up to a total of 100 The synergistic effect of combining DCB with the pyrimidine methanol of general formula () above is demonstrated in the following test. Test 1 DCB and α-(2-chlorophenyl)-α-(4-
The effectiveness of the combination with chlorophenyl)-5-pyrimidine methanol (hereinafter referred to as fenarimol) in inhibiting wheat leaf rust (Psinia recondata) was investigated in a greenhouse at 10, 20, or
25, 50, or
Measured in combination with 150ppm DCB. Fenarimol was also evaluated alone at 10, 20 or 40 ppm, and DCB was also evaluated alone at 25, 50 and 100 ppm active ingredient. This Fuenarimol is 1 lb/gal (453.59
Formulated as an emulsifiable concentrate (1EC) at 75% wettable powder (75WP)
It was formulated as. Treatment solution is Fenarimol 1EC
Alternatively, it was prepared by diluting DCB75WP with tap water to the required concentration. Wheat plants of the variety Monon were grown in plastic pots, with each pot containing approximately 50 wheat plants. When the plants had passed for 7 days, the plants in the two pots were sprayed with each treatment solution until liquid flow occurred. After drying, the plants were inoculated with wheat rust mold spores, the pots and plants were placed in a humid room for approximately 40 hours, and then transferred to a greenhouse to allow the disease to develop. Two weeks after transfer to the greenhouse, the treated plants were visually inspected to determine the percentage of disease development, and this number was converted to percentage disease control. The results are shown in Table 1.

[Table] Test 2 α-(2
-Chlorphenyl)-α-(4-fluorophenyl)-5-pyrimidine The effect of the combination of methanol (hereinafter referred to as Nuarimol) and DCB on suppressing Psinia recondata was investigated in a greenhouse at a Nuarimol concentration of 10, 20 or 40 ppm and was measured in combination with 25, 50 or 100 ppm chlorothalonil. This Nuarimol can also be used alone at 10, 20 or
Rated at 40ppm of active ingredient and also DCB alone
Active ingredient concentrations of 25, 50 or 100 ppm were evaluated. Formulations of test compounds, alone and in combination, were prepared as in Test 1 using tap water as the diluent. The Nuarimol-containing formulation was made from 0.75 pounds/gallon (340.19 g/4.54596) of Nuarimol-containing emulsifiable concentrate (0.75EC). Test wheat plants, Monon variety, were grown, treated with test chemicals in the same manner as described in Test 1, and inoculated with spores of the wheat leaf rust fungus described in Test 1. Controls consisted of plants treated with solvent only. Two weeks after the plants were transferred to the greenhouse, they were visually inspected to determine the disease attack rate, and this number was converted into a disease control rate. The results are shown in Table 2.

[Table] (Note) *Test not conducted

Claims (1)

[Claims] 1 2,4,5,6-tetrachloro-1,3-dicyanobenzene and general formula () (wherein X is chlorine or fluorine) in combination with pyrimidine methanol. 2 2,4,5,6-tetrachloro-1,3-dicyanobenzene and general formula () (wherein X is chlorine or fluorine) in combination with an inert carrier that is harmless to plants. 3. The sterilizer according to claim 1 or 2, wherein the weight ratio of pyrimidine methanol and 2,4,5,6-tetrachloro-1,3-dicyanobenzene is within the range of 1:400 to 1.6:1. Mold composition or formulation. 4 2,4,5,6-tetrachloro-1,3-dicyanobenzene and general formula () (wherein X is chlorine or fluorine) in combination with an inert carrier that is non-toxic to plants. 5. The production method according to claim 4, wherein the weight ratio of pyrimidine methanol and 2,4,5,6-tetrachloro-1,3-dicyanobenzene is in the range of 1:400 to 1.6:1. 6 2,4,5,6-tetrachloro-1,3-dicyanobenzene and general formula () A method for treating mold infection of cultivated plants, which comprises applying a mixture of pyrimidine methanol and pyrimidine methanol (wherein X is chlorine or fluorine) to cultivated plants after fruiting and before harvest.