JPS5912081B2 - Prunus elegans - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention is based on the general formula (wherein R and R1 represent a hydrogen atom or a methyl group 15, and n represents an integer of 1 to 2).

) The present invention relates to a herbicidal and fungicidal agent characterized by containing a compound represented by the following formula as an active ingredient.

The present inventors believe that the compound represented by the above general formula [1] exhibits excellent herbicidal activity against barnyard grass and many other common weeds in paddy fields and upland crops, with little decrease in herbicidal activity due to concentration dilution. The present invention was completed by discovering that Samurai has an excellent control effect against bacteria and pathogenic fungi that are harmful to rice and other cultivated plants, and there is no risk of phytotoxicity to useful plants.

The herbicidal fungicide of the present invention has both excellent herbicidal and fungicidal effects as described above, but as a fungicide, for example, white leaf blight of rice, gray rot of strawberries, blue mold of mandarin oranges, brown spot of apples, etc. It is also highly effective against soil-borne diseases such as damping-off caused by Rhizoctonia fungi and cotton rot caused by Pythium fungi, and is extremely effective in controlling these diseases. Next, a typical synthesis example of the active ingredient compound of the present invention will be described below.

Synthesis Example 1 Synthesis of 2,6-dichloro-4-nitrophenyl acrylate (compound 1) 2,6-dichloro-4-nitrophenol 8.3? (0.04 mol) and acrylic acid chloride 47 (0.044 mol) toluene 50ml
dissolve in j.

While cooling this solution to below 15°C, triethylamine 6
After adding 1 (0.06 mol), the mixture was heated to 50°C and reacted at the same temperature for 1 hour. After the reaction is complete, add 1 to the cooled reaction solution.
After removing triethylamine hydrochloride by adding 00 ml of water, the separated toluene layer is washed with a dilute aqueous sodium carbonate solution and then with water. After washing, the toluene layer was separated and dehydrated with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. From the residue, a crystalline solid consisting mostly of 2,6-dichloro-4-nitrophenyl acrylate 6,87 get.

This was dissolved in ligroin by heating, cooled, and recrystallized to obtain a purified product 4.4r having a melting point of 83 to 84°C. Elemental analysis value (%) (as C, H5Cl2NO4) *2・4-
Dichloro-6-nitrophenylcrotonate (compound 2
) Synthesis of 2,4-dichloro-6-nitrophenol8.
3t (0.04 mol) and 4.6y of crotonic acid chloride
(0.044 mol) is dissolved in 50 ml of dehydrated benzene.

While cooling this solution to below 15°C, 6V (0.06 mol) of triethylamine is added thereto, then heated to 50°C and reacted at the same temperature for 1 hour.

The following operation was performed according to Synthesis Example 1, and the majority of the results were 2 and 4.
A crystalline solid 7.2y consisting of -dichloro-6-nitrophenylcrotonate was obtained, which was dissolved under heating in n-hexane, and recrystallized after cooling to obtain a purified product 4.2y with a melting point of 45-46°C. 1V was obtained.

Elemental analysis value (%) (as ClOH7Cl2NO4) Other active ingredient compounds related to the present invention can also be synthesized by the same method as described above. Table 1 shows the physical properties of representative examples of these compounds. In the herbicidal and fungicidal agents of the present invention, the active ingredient compound represented by the general formula [1] may be used as is, but in general, depending on the purpose of use, it is carried out in a suitable liquid carrier (for example, an organic thickening agent). or mixed or adsorbed onto a suitable solid carrier (or diluent extender).

At that time, by appropriately adding various auxiliary agents (e.g. emulsifiers, dispersants, suspending agents, spreading agents, wetting agents, penetrating agents) as necessary, emulsions, wettable powders, granules, powders, etc. It can be used in various dosage forms such as aerosols. In addition, the herbicide and fungicide of the present invention can be used in combination with other herbicides, fungicides, insecticides, pesticides for plant growth regulation, soil conditioners, or fertilizing substances, as well as in combination with these. Preparations are also possible.

The content of the active ingredient compound in the weeding and sterilization of the present invention is 1 to 10% in granules, 40 to 80% in wettable powders, 1 to 10% in powders, and 10 to 50% in emulsions (all percentages by weight) is appropriate. Next, examples of the herbicide and fungicide of the present invention will be shown. [Parts] in the examples represent "parts by weight." The active ingredient compounds are shown in Table 1 and by the compound number of the synthesis example. Mackerel 1 Mix 15 parts of granule compound, 72 parts of bentonite, 20 parts of talc, 2 parts of sodium dodecylbenzenesulfonate, and 1 part of sodium ligninsulfonate, add an appropriate amount of water and knead, and then extrude into a granulator. The mixture was granulated using a conventional method to obtain 100 parts of granules.

Example 2 250 parts of a hydrating agent compound, 40 parts of diatomaceous earth, and 10 parts of sodium dodecylbenzenesulfonate were pulverized and mixed to form a hydrating agent 1.
Get 00 copies.

tExample 3 33 parts of a powder compound and 97 parts of clay were ground and mixed, and 100 parts of a powder was prepared.
get the part.

Example 4 510 parts of emulsion compound, Solpol 800A (Toho Chemical Co., Ltd.)
10 parts of emulsifier) and 80 parts of solvent naphtha were mixed to obtain 100 parts of an emulsion.

Next, the effects of the herbicidal and fungicidal agents of the present invention will be specifically explained using test examples.

Test example 1 Stalk treatment test (herbicidal effect) Inner diameter 18C! FL clay pots were filled with soil, and weed seeds and seeds of rice, corn, or wheat were seeded therein, covered with soil, and grown in a greenhouse.

When weeds and crops grow at the 3- to 4-leaf stage, a predetermined amount of the test compound is made into an emulsion or *heptahydrate form, diluted with an appropriate amount of water, and sprayed onto the foliage of the plants using a microsprayer. Spread all over. One month after spraying, the herbicidal effect on various weeds and the chemical damage to crops were investigated, and the results shown in Table 2 were obtained. In this table, the herbicidal effect or herbicidal damage of the test compound is classified into 6 levels, with ``0'' indicating no effect on the growth of weeds or crops, and 15'' indicating completely killing them. It was displayed. Test Example 2 Brackish soil treatment test (herbicidal effect) Paddy soil (14
(through mesh blue) 3.3kg a/50
00 into a Wagner pot, and add N. P2O5, K2
After applying 0.87 of each O to the entire layer with chemical fertilizer, apply an appropriate amount of Q
Add water and stir to make it hydrated.

To this, two paddy rice seedlings (seedlings, leaf cold 3, O) grown in advance in a greenhouse were used as one plant, and the two plants were transplanted and grown in the greenhouse. 4 {( At the beginning of weed emergence 5 days after paddy rice transplantation, a predetermined amount of the test compound was treated under stagnant water using granules prepared according to the method described in Example 1 above. Treatment 1 After several months, the weed growth status and the degree of chemical damage to paddy rice were investigated by observation, and the results shown in Table 3 were obtained.In this table, the display classification of the weed growth status is Test Example 1.
Similarly, there are 6 levels of chemical damage to paddy rice, and the display categories are ``severe damage,'' ``major damage,'' ``medium damage,'' ``slight damage,'' and ``slight damage.''
and [Harmless]. Please note that during the exam period, 1
1C per day! Due to FL leakage treatment, the depth of stagnant water in the pot has been reduced to 3? I kept it. Test example 3 Antibacterial activity test A predetermined amount of sugar-added yam broth agar medium was dispensed into test tubes, and after steam sterilization, an emulsion prepared in advance under sterile conditions was added to the predetermined concentration. , Shake well to mix and make a flat plate.

Next, the test bacteria that had been cultured in advance were inoculated onto the plate medium, and after being left in a constant temperature room at 28°C for 3 days, the elongation state of the hyphae was observed and measured, and the results shown in Table 4 were obtained.

The effectiveness of the test compound was classified and displayed in the following five stages.

4...Bacteria become dead and hyphae extension is not observed at all.

Claims (1)

[Claims] 1 General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R and R_1 represent a hydrogen atom or a methyl group,
n represents an integer of 1 to 2. ) A herbicidal and fungicidal agent characterized by containing a compound represented by the following as an active ingredient.