JPH0627115B2 - N- (2-chloro-4-trifluoromethylphenyl) -3-trifluoromethylbenzenesulfonamide and agricultural fungicide - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention is characterized by containing N- (2-chloro-4-trifluoromethylphenyl) -3-trifluoromethylbenzenesulfonamide and the compound. The present invention relates to an agricultural fungicide.

The compound of the present invention is agriculturally useful as a soil fungicide.

[Prior Art] One of the major obstacles in crop cultivation has been disease of crops. Among the diseases, soil diseases caused by soil pathogens are one of the most difficult problems.
Recently, in Japan, the growing area of vegetables has become a housing complex, and the tendency of continuous cropping of commercial crops has become stronger, and the control of soil diseases has become more and more important. However, originally, controlling soil diseases is extremely difficult, and damage tends to increase more and more. For example, for root-knot disease of cruciferous vegetables,
PCNB (pentachloronitrobenzene) is used as a silver bullet, but its application amount is so large that it is called fertilizer-like. In addition, in fields in which cruciferous vegetables are continuously grown, standard effects have already been insufficient, and it is common knowledge to use larger amounts. By the way, environmental pollution of pesticides has become a social problem, and there is no reason for such drugs used in large amounts to be left unattended, and there is a strong demand for effective drugs with lower doses to replace them. . Other soil diseases such as potato scab, potato powder scab, sugar beet root rot, wheat stripe dwarf, radish fissure browning, turnip root constriction, pea root rot, big vein disease of lettuce, etc. On the other hand,
Complete disease control with almost all drugs is considered difficult.

A large number of sulfonamide compounds have been synthesized for a long time, and many studies have been conducted on their physiological activity. In the field of agriculture, insecticides as well as herbicides and fungicides have been studied. For example, examples of herbicides include Japanese official publication No. 39-29571 and 40-19199.
There is a Japanese patent publication Sho 44-9.
Nos. 304, 45-6836, 46-6797, 47-15119, and JP-A-57-31655, 58-118558, 58-219159 and the like. Also, as an insecticide, US Patent 3,034,955 (1962)
Can be given.

U.S. Pat. No. 3,034,955 discloses compounds of the formula: and others.

Here, n represents an integer of 1 to 2 and m represents an integer of 1 to 2. The compounds disclosed in US Pat. No. 3,034,955 are disclosed to have insecticidal activity, but there is no disclosure or suggestion of bactericidal activity.

In addition, Japanese Patent Publication No. 58-11858 and 58-219.
No. 159 discloses a control effect of a sulfonamide derivative against clubroot disease of cruciferous vegetables, but the sulfonamide derivative is limited to a 3-nitrobenzenesulfonamide derivative.

[Problems to be Solved by the Invention]

The present invention has a broader spectrum than conventionally known fungicides for soil diseases, and is highly active, effective at a low dose, and has less environmental impact, soil fungicidal compounds and soil diseases. An object is to provide a bactericidal composition.

[Means and Actions for Solving the Problems]

The present inventors focused their attention on the fact that sulfonamide derivatives have various physiological activities in order to solve the above-mentioned problems, and as a result of diligent studies on sulfonamide derivatives, various plant diseases, in particular, there is no excellent control agent to date. The present invention has been completed by finding a compound having a broad spectrum against soil diseases, which is completely unpredictable from known literatures, and having highly active soil bactericidal properties.

That is, the compound according to the present invention is N- (2-chloro-4
-Trifluoromethylphenyl) -3-trifluoromethylbenzenesulfonamide, which is a new and novel compound.

The compounds of the present invention are distinct from the compounds disclosed in Japanese Patent Publication Nos. Sho 58-118558 and Sho 58-219159 in structure. As is apparent from the above-mentioned prior art, the sulfonamide derivatives exhibit different physiological activities due to the difference in their structures, and the compounds of the present invention have a broad spectrum and high activity against soil diseases. It cannot be predicted from the above-mentioned prior art that it has a controlling effect. Also, U.S. Patent 3,034,955
It is difficult to predict that the compound of the present invention has a high activity as a soil fungicide from the insecticidal active substance disclosed in US Pat.

The compound of the present invention is synthesized by the reaction represented by the following formula.

Pyridine, triethylamine, trimethylamine and the like are preferable as the base used in the reaction, but pyridine is most suitable. As the reaction solvent, an inert organic solvent such as toluene, xylene, chlorobenzene or dichlorobenzene can be used, and one having a boiling point of 110 ° C. or higher is suitable. The reaction temperature and reaction time vary depending on the solvent used, but the reaction temperature is preferably 110 to 180 ° C., and the reaction time is preferably 5 to 15 hours.

INDUSTRIAL APPLICABILITY The compound of the present invention exhibits antibacterial activity or growth inhibitory activity against various plant pathogens, and can be applied to a wide range of plant diseases, but particularly shows excellent effects against soil diseases of various crops for which there is no effective control agent up to now. . For example, root-knot disease of cruciferous vegetables, powdery scab of potato, root scab of sugar beet, stripe rot of wheat, wilt of sugar beet, root rot of sugar beet, crack browning of Japanese radish, turnip of turnip Root constriction,
It has an excellent control effect against root rot of pea, big vein disease of lettuce, various bacterial wilt diseases. It also shows antibacterial activity against Gram-positive bacteria against bacteria.

When the compound of the present invention is used as a soil treatment agent, its application amount varies depending on the type of target disease, various conditions such as soil conditions (PH, water content, organic matter content, etc.) and meteorological conditions. It is effective in the range of 0.2 to 40 kg, preferably 0.5 to 20 kg per hectare.

The compound of the present invention may be used as it is, but usually, a carrier and, if necessary, other auxiliary agents are added and mixed,
Formulation form For example, it is prepared into a powder, a wettable powder, a granule, a flowable agent, etc. before use. As the carrier, clays, talc, bentonite, calcium carbonate, diatomaceous earth, zeolite, inorganic substances such as silicic acid anhydride, wheat flour, soybean flour, starch, vegetable cellulose such as crystalline cellulose, petroleum resin,
Examples thereof include polymer compounds such as polyvinyl chloride and polyalkylene glycol, urea, waxes and the like. Examples of the liquid carrier include various oils, organic solvents and water.

Further, auxiliary agents required for the formulation, such as wetting agents, dispersants, sticking agents, spreading agents, etc., can be appropriately used alone or in combination as necessary.

As auxiliary agents used for the purposes of wetting, dispersion, spreading, component stabilization, physical property stabilization, rust prevention, etc., various surfactants and gelatin, albumin, sodium alginate, methyl cellulose, carboxymethyl cellulose, polyvinyl alcohol, xanthan gum Polymer compounds such as and other auxiliary agents. In the case of a flowable agent, an industrial bactericidal agent may be added depending on the case in order to prevent bactericide and mildew.

Examples of the surfactant include non-polymers such as those obtained by polymerizing ethylene oxide with alkylphenols, higher alcohols, alkylnaphthols, higher fatty acids, fatty acid esters, dialkylphosphate amines, etc., and those obtained by polymerizing ethylene oxide and propione oxide. Ionic surfactant,
Alkyl sulphates such as sodium lauryl sulphate, alkyl sulphonates such as sodium 2-ethylhexene sulphonate, anionic surfactants such as aryl sulphonates such as sodium lignin sulphonate and sodium dodecylbenzene sulphonate and various Examples include cationic and zwitterionic surfactants.

Further, when using the compound of the present invention as a fungicide, at the same time, other pesticides such as insecticides, fungicides, acaricides, nematicides, antiviral agents, herbicides, plant regulators, attractants, etc.
Not only can it be used in combination with a soil conditioner such as lime or a fertilizing substance, but a mixed preparation with these is also possible.

The various formulations or spray preparations containing the compounds of the invention can be applied according to the generally customary application methods. That is, dusting (eg, dusting, dusting,
Liquid spraying), soil surface application, soil admixture application, surface application (for example, application, dressing, coating), seed dipping, root dressing of seedlings, root dipping and the like.

The active ingredient in various dosage forms is usually 0.1 to 10% by weight for powders, 20 to 90% by weight for wettable powders, and 0.1 to 1 for granules.
0% by weight, and 20 to 90% by weight for a flowable agent is desirable.

〔Example〕

Next, the synthetic method of the compound of the present invention will be described in detail with reference to specific synthetic examples.

Synthetic Example N- (2-chloro-4-trifluoromethylphenyl) -3-tolylo-o-methylbenzenesulfonamide 400 ml Orthodichlorobenzene 200 m in a flask.
1, pyridine 1 ml and 2-chloro-4-trifluoromethylaniline 2.0 g (0.01 mol) were charged and 3-trifluoromethylbenzenesulfochloride 2.
5 g (0.01 mol) was added slowly at room temperature over 5 minutes. Then, the mixture was heated and stirred under reflux (175 to 180 ° C.) for 6 hours. The reaction solution was cooled to room temperature, washed thoroughly with dilute hydrochloric acid and then with water, dehydrated with anhydrous sodium sulfate, and orthodichlorobenzene was distilled off under reduced pressure. The residue is subjected to silica gel column chromatography (developing solution: benzene).
The desired compound was isolated by. mp121-123
℃, yield 2.2g, yield 55% Infrared absorption spectrum Next, formulation examples of the bactericide containing the compound of the present invention as an active ingredient are shown, but the kind and mixing ratio of the addition aid are not limited thereto.

Formulation Example 1. Powder 3 parts by weight of the compound of the present invention, 10 parts by weight of Carplex # 80 (white carbon manufactured by Shionogi & Co., Ltd.), clay 8
7 parts by weight were mixed and pulverized to obtain a powder containing 3% by weight of the compound of the present invention as an active ingredient.

Formulation Example 2. Dust formulation 0.5 part by weight of the compound of the present invention, calcium carbonate 49.5 parts by weight,
50 parts by weight of clay was mixed and pulverized to obtain a dust containing 0.5% by weight of the compound of the present invention as an active ingredient.

Formulation Example 3. Dust formulation 1 part by weight of the compound of the present invention, Adeka Estol EX-130
5 parts by weight of 3 (manufactured by Asahi Denka Co., Ltd.), 44 parts by weight of calcium carbonate and 50 parts by weight of clay were mixed and pulverized to obtain a dust containing 1% by weight of the compound of the present invention as an active ingredient.

Formulation Example 4. Wettable powder 50 parts by weight of the compound of the present invention, Solpol (Toho Chemical Co., Ltd.)
5 parts by weight of surfactant) and 45 parts by weight of Radiolite (calcined diatomaceous earth manufactured by Showa Kagaku Co., Ltd.) were uniformly pulverized and mixed to obtain a wettable powder containing 50% by weight of the compound of the present invention as an active ingredient.

Formulation Example 5. Wettable powder 80 parts by weight of the compound of the present invention, 5 parts by weight of Carplex # 80 (white carbon manufactured by Shionogi Pharmaceutical Co., Ltd.), 3 parts by weight of Emar 10 (surfactant manufactured by Kao Corporation), clay 12
The parts by weight were uniformly mixed and pulverized to obtain a wettable powder containing 80% by weight of the compound of the present invention as an active ingredient.

Formulation Example 6. Granules 10 parts by weight of the compound of the present invention, 2 parts by weight of sodium dodecylbenzenesulfonate, 1 sodium ligninsulfonate.
Parts by weight, 25 parts by weight of talc and 62 parts by weight of bentonite are uniformly mixed, hydro-kneaded, and then granulated using an extrusion granulator, and after drying, a granule containing 10% by weight of the compound of the present invention as an active ingredient is obtained. Obtained.

Formulation Example 7. Granules Granules 96 parts by weight of calcium carbonate and ADEKA Estol EX
-1303 (Asahi Denka Co., Ltd.) 1 part by weight is uniformly mixed,
3 parts by weight of a pulverized product of the compound of the present invention was added thereto and mixed to obtain a granule containing 3% by weight of the compound of the present invention as an active ingredient.

Formulation example 8. Mixed granules with fertilizer 97 parts by weight of granular chemical fertilizer and Dolores A (Sankyo Co., Ltd.)
1 part by weight) was uniformly mixed, and 2 parts by weight of the compound of the present invention was added thereto and mixed to obtain a mixed granule with a fertilizer containing 2% by weight of the compound of the present invention as an active ingredient.

Formulation Example 9. Granules mixed with fertilizer 92 parts by weight of granular chemical fertilizer and Adeka Estol EX-1
2 parts by weight of 303 (manufactured by Asahi Denka Co., Ltd.) were uniformly mixed, and 6 parts by weight of the compound of the present invention was added and mixed therein to obtain a mixed granule with a fertilizer containing 6% by weight of the compound of the present invention as an active ingredient. .

Formulation Example 10. Flowable Agent 40 parts by weight of the compound of the present invention, 9 parts by weight of sodium lignin sulfonate, 1 part by weight of gum arabic, and 50 parts by weight of water are mixed and pulverized using a sand grinder, and 40% by weight of the compound as an active ingredient. A flowable agent containing was obtained.

Test Example 1. Chinese cabbage clubroot control test (Plasmodiophora brassica)
To 1 kg of soil contaminated with e), a prescribed amount of the dust preparation prepared according to Formulation Example 1 is added, mixed well, and then placed in a clay pot with a diameter of 15 cm. 20 seeds of Chinese cabbage (variety: Muso) were sown on this. This was grown in a greenhouse, and 6 weeks after sowing, the presence or absence of root disease was investigated. The control effect was shown by obtaining the control rate from the following formula. The results are shown in Table-1.

Test Example 2. Komatsuna seedling wilt control test using Aphanomyces raphani To 1 kg of sterilized soil, a predetermined amount of the dust preparation prepared according to the method of Formulation Example 2 was added, and well mixed with the total amount of soil, and then a diameter of 15
Filled in a cm clay pot, Komatsuna (variety: New late-night Komatsuna)
20 seeds were sown. 5 days after sowing, zoospore suspension of Aphanomyces raphani prepared in advance (50 cells / 1
The field of view (150 times) was irrigated with 50 ml of soil per pot and inoculated. This was grown in a greenhouse for another 30 days, and the presence or absence of disease was observed and evaluated one by one. The control effect was expressed by the control rate shown in Test Example 1. The test was performed in triplicate. The results are shown in Table 2 as an average value of 3 replicates.

Test Example 3. Pea root rot control test To 1 kg of soil contaminated with pea root rot fungus Aphanomyces euteiches, a predetermined amount of the dust preparation prepared according to Formulation Example 3 was added, mixed well with the total amount of soil, and the diameter was measured. Ten pea seeds were sown in a 15 cm unglazed pot. This was grown in a greenhouse, and 30 days after seeding, the strain was extracted and the degree of disease onset was observed and evaluated. The control effect was expressed by a 4-step method of the degree of disease on a scale of 0 to 3, and this was expressed as the degree of disease by the following formula. The test was performed in triplicate. The results are shown in Table 3 as an average value.

Disease severity index 0: No disease 1: Browning of the edge area 2: Low 〃 High 3: Dead or just before death Test Example 4. Sugar beet wilt control test To 1 kg of sterilized soil, a predetermined amount of powder prepared according to the method of Formulation Example 2 was added, mixed well, and then packed in a clay pot with a diameter of 15 cm. : Monohill) 20 seeds were sown. 3 days later, zoospore suspension of Aphanomyces cochilioides (50 /
1 field, 150 times) was inoculated into each pot at a rate of 50 ml. The seedlings were cultivated in a greenhouse, and the growth condition of the seedlings was observed and evaluated 10 days after the inoculation, and the control rate was calculated by the following formula. The results are
4 shows.

Test Example 5. Potato Scab Disease Control Test Potato scab disease bacteria cultivated in an oatmeal liquid medium in advance are mixed with soil to form a contaminated soil. This soil 8
A predetermined amount of the dust preparation prepared according to the method of Formulation Example 2 was added to kg, thoroughly mixed, and then filled in a resin pot of 1/2000 are and seeded with potato (variety: male shak).
This was grown outdoors, and tubers were dug 80 days after sowing, and the disease state was investigated. In the investigation, one tuber weighing about 20 g or more was observed and evaluated in five stages of "0" to "4", the disease degree was determined by the following formula, and the control effect was tested. The results are shown in Table-5.

Disease severity index 0: No lesions 1: 1 to 3 lesions or areas of lesions 3% or less 2: 410 〃 〃 4 to 13% 3: 11 to 20 〃 〃 14 to 25% 4: 21 or more 〃 〃 26% or more [Effect of the invention] As is clear from the results of the above test examples, the compound of the present invention is root-knot disease of cruciferous vegetables, potato scab, powdery scab and soil diseases caused by various aphanomyces bacteria, Shows excellent control effect. There is no excellent control agent for any of these soil diseases, which have been regarded as problems as difficult control diseases.

Although some of the agents are commercially available, the compound of the present invention is clearly superior to these and extremely useful as a soil fungicide.

Further, the compound of the present invention can be expected to have a sufficient controlling effect against soil diseases caused by fungi similar to the pathogenic bacteria of these various soil diseases such as root-root disease of sugar beet and stripe dwarf disease of wheat.

It is clear that the compound of the present invention has a broader spectrum than the conventionally known fungicides for soil diseases, is highly active, and is a fungicide for soil diseases with less influence on the environment.

 ─────────────────────────────────────────────────── ─── Continuation of the front page Examiner Osamu Sato

Claims (2)

[Claims] 1. N- (2-chloro-4-trifluoromethylphenyl) -3-trifluoromethylbenzenesulfonamide. 2. An agricultural fungicide containing N- (2-chloro-4-trifluoromethylphenyl) -3-trifluoromethylbenzenesulfonamide.