JPS591269B2 - Thiadiazine derivative - Google Patents

Description

Detailed Description of the Invention The present invention is based on the following general formula (1) RIN/C-NN R2/\C-N' width [R1 is R3COCH2CH2- group, R3CH(OH)CH2CH2- group, ( R3 represents a lower alkyl group) or a piperidino group, and R2 represents a hydrogen atom or a piperidino group].

More specifically, the present invention relates to providing a novel thiadiazine derivative useful as an agricultural and horticultural fungicide, particularly as a rice blast control agent. The present inventors synthesized various novel thiadiazine derivatives and conducted extensive studies on their usefulness. As a result, it was discovered that a specific thiadiazine derivative represented by the above general formula is useful as an agricultural and horticultural fungicide, particularly as a rice blast control agent, and the present invention was completed. Next, examples of the present invention are shown below, but the present invention is not limited to the following compounds, reaction conditions, etc. Example 1 4-(3-oxobutyl)-2,6-dicyclohexyl 3,5-dioxoperhydro 1,2,6-thiadiazine-Production process for 1,1-dioxide/\Reaction formula: CH3SO2+CH2=CHC00CH3 \C
-N/(convex width (■)) Production method: 2,6-dicyclohexyl-3,5-dioxoperhydro-1,2,6-thiadiazine () 6.519 (0.
02 mol), methyl vinyl ketone 1.549 (0.02 mol), methyl vinyl ketone 1.549 (0.02 mol)
2 mol) and powdered K2CO3 (0.04 mol) were added to ethyl acetate 45Tf11, refluxed for 6 hours, and filtered while hot.

The bottom liquid was distilled off, and the residue was dissolved in 30 ml of water and treated with decolorizing charcoal when cold. Neutralize the solution with hydrochloric acid to make it weakly acidic and filter out the precipitate and wash with water. Ethyl acetate was dissolved in 50 ml of water (separated from house to house) in a bath of 50 mL of water, filtered, and neutralized with hydrochloric acid to make it weakly acidic. The precipitate was washed with water, combined with the crystals, and recrystallized from methanol. The purpose of yellow needle crystals is 1V.
) 5.9y was obtained. The melting point is 105°C, and the elemental analysis values are as follows.

Molecular formula Cl, H3ON2O5S Example 2 4-(3-hydroxybutylene)-2,6-dicyclohexyl-3,5-dioxoperhydro-1,2,6
-Production method of thiadiazine-1,1-dioxide Production method: 0.37 y of caustic soda is dissolved in 6.7 ml of water.

Add 13 ml of methanol to this and compound (1V) 2,9
Add and dissolve 9y (0.0075 mol). Furthermore, while stirring at room temperature, NaBH4l,33y was gradually added 2
Stir for 1 hour and further stir at 60° C. for 30 minutes. After that, methanol was distilled off under reduced pressure, and 10 ml of water was added to the residue.
Gradually add hydrochloric acid under ice cooling to make it weakly acidic. The precipitate was collected, washed with water, and then recrystallized from methanol to obtain the desired product (
Obtained 2.4y.

The melting point was 143° C., and the elemental analysis values were as follows.

Molecular formula Cl9H32N2O5S Example 3 4,4-diperidino-2,6-dicyclohexyl3,5
-Production method of dioxoperhydro-1,2,6-thiadiazine-1,1-dioxideProduction method: 4-bromo-2,6-dicyclohexyl-3,5dioxoperhydro-1,2,6-thiadiazine 1 , 1-dioxide EIT) 3.3y (0.008 mono(c),
1.59 (0.018 mol) of piperidine was added to 30Tf11 of dry benzene and heated under reflux for 4 hours.

After cooling, the precipitate is removed, the remaining liquid is distilled off, and the residue is washed with water. Recrystallization from ethyl acetate yielded 1.1y of the desired product () as yellow needle-like crystals. The melting point is 178°C and the elemental analysis values are as follows.

Molecular formula C25H42N4O4S Representative examples of the above general formula are shown in the following table.

In addition, compound deterioration is also referred to in the following test examples. Next, the usefulness of the new substance according to the present invention will be explained using test examples. Test Example Paddy rice blast control effect test Paddy rice grown in clay pots with a diameter of 9CTI1 in a greenhouse (
Cultivar: Asahi) was produced in the third leaf stage seedling according to Example 1,
A powder agent (equivalent to 3k9 per 10 ares) was uniformly spread using a benziya duster.

After spraying, leave overnight under humid room conditions (humidity 95-100%, temperature 24%).
One day after the spraying, a spore suspension of the blast fungus was inoculated by spraying. Five days after inoculation, the number of lesions per leaf on the third leaf was investigated, and the control value was calculated using the following formula. The test results are shown in the table below.

The comparative drug in the table has the chemical name 0-ethyl S. It is a commercially available disinfectant [generic name (EDDP)] containing S-diphenylphosphorodithiolate as an active ingredient. The substance according to the present invention can be formulated into a desired form such as a powder, wettable powder, emulsion, fine granule, or granule by adding various carriers and auxiliary agents in the same manner as conventional agricultural and horticultural fungicides. can be used. Examples of formulations are shown below. Formulation example 1 (powder) Compound/F6l 2 parts (parts by weight, same hereinafter), clay 98
Mix and crush the remaining parts to make a powder.

Formulation example 2 (hydrating powder) Compound 270 parts, calcium lignin sulfonate 2 parts, calcium alkylbenzenesulfonate 3 parts, polyoxyethylene nonyl phenyl ether 5 parts, and white clay 2 parts
0 parts are uniformly mixed and finely ground to obtain a wettable powder containing 70% of the active ingredient in the form of a fine powder with a uniform composition.

Formulation Example 3 (Emulsion) Parts of compound/F636O, 17 parts of polyoxyethylene phenyl ether and 23 parts of xylene are mixed and dissolved to obtain an emulsion containing 60% of the active ingredient.

Claims (1)

[Claims] 1 General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [However, R_1 is ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ Group ▲
There are mathematical formulas, chemical formulas, tables, etc. Thiadiazine derivatives represented by the ▼ group (R_3 represents a lower arginine group or a piperidino group, and R_2 represents a hydrogen atom or a piperidino group).