JPS63267754A - Benzamide derivative and soil disease-controlling agent - Google Patents

Abstract

NEW MATERIAL:A compound expressed by formula I (X is halogen; n is 1 or 2). EXAMPLE:N-(2,4,6-Triisopropylbenzenesulphonyl)-2,6-dichlorobenzamide. USE:A soil disease controlling agent exhibiting excellent activity against Plasmodiophora occurring in Brassicaceae plant and completely providing no phytotoxicity to useful crops. PREPARATION:A halogen substituted benzoic acid halide expressed by formula II (X is halogen) is reacted with 2,4,6-triisopropyl-benzenesulfoneamide in the presence of a dehydrochlorination agent (e.g. sodium hydroxide) in a solvent such as dioxane at room temperature - boiling point of the solvent to provide the aimed compound expressed by formula I.

Description

Detailed Description of the Invention [Field of Industrial Application] The present invention relates to a novel benzamide derivative or a salt thereof, and a soil disease control agent characterized by containing the derivative or a salt thereof as an active ingredient. It is.

The above-mentioned compound of the present invention is a new compound that has not been described in any literature, and is highly effective against soil diseases such as clubroot disease that occurs in cruciferous plants, and is also highly effective against useful crops (without phytotoxicity). It is something that

[Conventional technology]

Continuous cropping failure is one of the important problems in agricultural production, and most of the causes are caused by soil diseases. Control of conventional soil diseases is extremely difficult due to the ecology of their occurrence, and the development of superior control agents is desired. has increased, causing great damage to the production of Chinese cabbage, cabbage, turnips, etc.

Furthermore, beet root disease is caused by a soil-dwelling fungus called Polymyxa bitterae, which is transmitted by the beet necrotic yellow vein virus, and the area where it occurs is currently expanding and the damage is increasing. . Potato scab also causes great damage to potato production.

However, although various chemical control methods are currently being used to control soil diseases, sufficient control effects have not been obtained.

In particular, various chemical control methods have been used to control the clubroot disease that occurs in cruciferous plants, but current commercially available drugs (the active ingredient of which is pentachlornitrobenzene, for example) are unable to produce good results. It is in. In other words, a sufficient control effect cannot be achieved unless the commercially available drug is applied in large amounts.On the other hand, if it is applied in large amounts, there may be problems with safety and environmental pollution.Although the compound of the present invention is a new compound, We have completed the present invention by discovering that this is highly effective against soil diseases, particularly clubroot disease that occurs in cruciferous plants.

Incidentally, as well-known documents, JP-A dsso-152401 and JP-A 62-16465 are known.

JP-A-60-152401 discloses certain benzamide derivatives, and describes that these are useful as disease control agents for agricultural and horticultural use, and particularly exhibit outstanding control effects on rice blast. However, the novel compound of the present invention
Specifically, all (not disclosed), and control of soil diseases is not disclosed at all.
No. 6465 also discloses specific benzamide derivatives and discloses that these are effective in controlling soil diseases. However, the compound of the present invention is not specifically disclosed at all.

[Aspects of the invention]

The present invention provides benzamide derivatives represented by general formula (I): (wherein, X represents a halogen atom, and n represents an integer of 1 or 2) or salts thereof, and at least one thereof as an active ingredient This invention relates to a soil disease control agent characterized by containing:

In the compound of the present invention represented by the above general formula (1),
For example, a chlorine atom, a bromine atom, an iodine atom, and a fluorine atom can be mentioned, but a chlorine atom is preferable, n is preferably 2, and the substitution positions of X are preferably the 2-position and the 4-position.

Examples of these salts include alkali metal salts such as sodium and potassium, alkaline earth metal salts such as calcium and magnesium, various amine salts, and various quaternary ammonium salts.

The compound of the present invention is a new compound that has not been specifically disclosed in any known literature, and has excellent control effects against soil diseases and has no phytotoxicity on useful plants, making it excellent for practical use. It is a soil disease control agent.

The compound of the present invention is approximately 10 times more effective in controlling soil diseases than the compounds specifically described in the above-mentioned known literature; for example, the compound of the present invention has a soil disease control effect of 0.2 kg/
Some compounds have a sufficient control effect even at a treatment amount of 2 kg/ha, but some known compounds have some control effect even at a treatment amount of 2 kg/ha, but some have no effect at all.

On the other hand, in the case of the compounds of the present invention, almost no phytotoxicity is observed even at a treatment rate of 10 Kg/ha, but in the case of known compounds, phytotoxicity is observed even at a treatment rate of 1 Kg/ha.

That is, the compounds of the present invention are extremely superior to known compounds both in terms of soil disease control effect and in terms of phytotoxicity, and this is specifically described in the test examples below.

(Hereinafter, blank spaces) The compound of the present invention can be easily synthesized by the method shown below.

(II) CH(CHj)z (in the above formula, X and Y are halogen atoms, n is 1 or 2
In other words, the compound (I) of the present invention can be obtained by condensing a halogen-substituted benzoic acid halide (n) and 2.4.6-)lyisopropylbenzenesulfonamide. This reaction is preferably carried out in the presence of a dehydrochlorinating agent, such as hydroxides such as sodium hydroxide and potassium hydroxide, carbonates such as sodium bicarbonate, sodium carbonate, and potassium carbonate; Examples include amines such as triethylamine and pyridine. The condensation reaction is preferably carried out in a solvent inert to the reaction.

Examples of impermeable solvents include aromatic hydrocarbon solvents such as benzene, toluene, and xylene, diethyl ether,
Examples include ether solvents such as tetrahydrofuran and dioxane, ketone solvents such as acetone and methyl ethyl ketone, and these can be used alone or in combination.

Although the reaction temperature can be set between room temperature and the boiling point of the solvent used, it is most advantageous for scraping to be set at the boiling point of the solvent. Those skilled in the art can easily set appropriate reaction conditions.

The method for obtaining the compound of the present invention will be shown below in more detail through Examples, but the present invention is not limited to these Examples.

(Hereinafter, blank space) Synthesis of N-(2,4,6-)liisopropylbenzenesulfonyl)-2,6-dichlorobenzamide (compound Na9) 8.50 g (0,03
0 mol) of 2.4.6-) lyisopropylbenzenesulfonamide, 5.40 g (0.039 mol) of potassium carbonate and 70-1 of dioxane. 2゜6-dichlorobenzoyl chloride 6 was added to this solution at room temperature.
．． 28 g (0,030 mol) of a 30-1 dioxane solution was added dropwise with stirring. After the completion of the dropwise addition, the reaction solution was heated and stirred under dioxane reflux for 5 hours. After cooling,
Insoluble matter was filtered off and washed with 3 liters of dioxane. Combine the filtrate and washing liquid, concentrate under reduced pressure, and add 200 s of ice water to the residue.
was added, acidified with hydrochloric acid, and the separated oil was extracted with 200 ml of ethyl acetate, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue is recrystallized from a 1:1 mixed solvent of toluene:ethanol, collected by filtration, and dried to obtain the desired N-(2,4,6-triisopropylbenzenesulfonyl)-2,6-cyclobenzamide. 10.2
7g was obtained.

(Sheet weight 75.0%, melting point 217-220℃) Elemental analysis value 0% 8% N% calculated value 57,89
5,96 3.07 Actual value 57,70 6,
00 3.11m Synthesis of N-(2,4,6-triisopropylbenzenesulfonyl)-2,4-dichlorobenzamide (compound NcL8') Using a 200 ml 4-pro flask, the charging molar ratio was the same as in Example 1. Then, the solvent was changed to acetone, and the mixture was heated and stirred for 8 hours under reflux of acetone. After cooling, the same treatment as in Example 1 was performed to obtain 9.51 g of target N-(2,4,6-triisopropylbenzenesulfonyl)-2,4-dichlorobenzamide.

(Sheet weight 69.5%, melting point 188-191℃) Elemental analysis value 0% 8% N% calculated value 57,89
5,96 3.07 Actual value 57.74 6.
02 3.04M Synthesis of N-(2,4,6-)lyisobrobylbenzenesulfonyl)-4-chlorobenzamide (compound inhibition 3) 2.83 g (0,01
0 mol) of 2.4.6-) lyisopropylbenzenesulfonamide, 0.95 g (0.012 mol) of pyridine and 30a+1 of tetrahydrofuran. In this solution at room temperature, 4-chlorobenzoyl chloride 1
．． 75 g (0,010 mol) of a 1O2 tetrahydrofuran solution was added dropwise with stirring. After the completion of the dropwise addition, the reaction solution was heated and stirred for 4 hours under refluxing tetrahydrofuran.

After cooling, it was poured into 200 ml of diluted hydrochloric acid, and the separated oil was extracted with 200 ml of ethyl acetate. 2.05 g of benzenesulfonyl)-4-chlorobenzamide was obtained.

(Sheet weight 48.5%, melting point 218-221"C) Elemental analysis value 0% 8% N% calculated value 62.62
6,69 3.32 Actual value 62,48 6
, 75 3.40 Next, examples of compounds included in the present invention are shown in Table 1 below along with the compounds synthesized in the above examples.

However, the compounds of the present invention are not limited to these.

Table 1 Compounds represented by C0(CHs)z Compound No. Xn Melting point ('C)1
2-C1194~1972 3
-CI 185-1873 4-C
I 218-2214 3, 4-C
1g 202-2045 3.5-C
12175-1906 2.5-t, tz
1B3-189 No. 3-(Continued) Compound No. 1, Melting point ("C) 7
2.3-C12159-1718
2+4-ctz 188-1919
2,6-C12217-22010 2
．． 6-P! 190-19311 2
-Br 141-14312 3-
Br 188-19013 4-B
r 209-21114 3-I
195-19815 4-1
210-21216 2.5-Br.

17 2.4-Brx (Hereinafter, blank) When applying the compound of the present invention as a soil disease control agent, generally a suitable carrier such as a solid carrier such as clay, talc, bentonite, diatomaceous earth, calcium carbonate, or water, alcohol ( methanol, ethanol, etc.), aromatic hydrocarbons (benzene, toluene, xylene, etc.), chlorinated hydrocarbons, ethers, ketones, esters (
(ethyl acetate, etc.), acid amides (dimethylformamide, etc.), and can be used in combination with liquid carriers such as emulsifiers, dispersants, suspending agents, penetrating agents, spreading agents, stabilizers, and adjuvants, if desired. It can be put to practical use in any desired dosage form, such as a liquid, emulsion, wettable powder, powder, or granule.

In the case of solid dosage forms (powders, granules, wettable powders, etc.), the content of the compound of the present invention is not particularly limited, but is preferably about 0.1 to 60% by weight, and further,
It is preferably about 0.5 to 30% by weight.

On the other hand, in the case of liquid dosage forms (emulsions, solutions), the content of the compound of the present invention is not particularly limited, but is preferably about 0.5 to 90% by weight, and more preferably 2 to 90% by weight.
80! One of the methods for treating the soil with the preparation of the present invention, which is preferably about %, is to directly treat the soil and mix with the soil in the case of powders and granules. Although not particularly limited,
The amount per hectare is preferably about 0.01 to 200 kg, more preferably about 0.1 to 100 kg.

Another method is to dilute emulsions, solutions, and wettable powders with water to adjust the concentration of the compound of the present invention to a predetermined concentration, and then irrigate them into the soil. In this case, the concentration of the compound of the present invention is not particularly limited, but is preferably 1 to 2000 ppm+, more preferably 50 to 1 ppm+.
The amount of the compound of the present invention to be treated is preferably about 1000 pp, and is not particularly limited, but is preferably about 0.01 to 200 kg per hectare, more preferably about 0.1 to 100 kg.

Among the preparations of the present invention, powders are particularly preferred, and solid carriers for the second powder are not particularly limited, but clay, talc, calcium carbonate, and diatomaceous earth are preferred, and one or more of these are preferred. can be used. In addition, white carbon may be added as an auxiliary agent if necessary.The preferred blending ratio is 1 to 20% of the compound of the present invention.
60 to 99 parts by weight of clay, talc, calcium carbonate or diatomaceous earth, and 0 to 20 parts by weight of white carbon (auxiliary agent) may be optionally blended.

The soil diseases that can be controlled in the present invention are not particularly limited, and include, for example, clubroot of cruciferous plants, scab of beets, scab of potatoes, and the like.

Next, examples of formulations of soil disease control agents containing the compounds of the present invention as active ingredients are shown, but the soil disease control agents of the present invention are not limited to these. In the following formulation examples, "part" is Means parts by weight.

Example of Juice” 2 Wettable powder Compound of the present invention −・−・−・・−−−−−25
Part Sieglite A ----------------
−−−−−−−−−69 parts (Kaolin clay: Sieglite Kogyo ■Product name) Tsurupol 5039 ・−・−−
---1---3 parts (Mixture of nonionic surfactant and anionic surfactant: Toho Chemical ■Product name) Carplex (anti-caking agent) ---3 parts (White Carbon: Shionogi & Co., Ltd. trade name) The above is mixed and pulverized uniformly to make a wettable powder. When using, add 2 of the above hydrating agents.
Use after diluting 50 to 25,000 times.

II emulsion Compound of the present invention -11--------
---50 copies ---
・−−−−−−−−−−−−25 parts dimethylformamide ・−−−−−−−−−−= 20 parts Tsurpol 2
680 -·-m---·································· 5 parts (Mixture of nonionic surfactant and anionic surfactant: Toho Chemical ■ trade name) The above is mixed uniformly to form an emulsion. When used, the above emulsion is diluted 500 to 50,000 times.

Example 1 - Powder Compound of the present invention ---m-・------5 parts Clay ・----1------
・Mix 95 parts or more evenly to obtain a powder containing 5% of the active ingredient.

1 Gotsudo Powder Compound of the present invention ・----1-・-・-・・-・
1 part talc, ・−−−−−−−−−−−−
--= 99 parts or more are mixed uniformly to obtain a powder containing 1% of the active ingredient.

Satsuki ■ Powder Compound of the present invention ・−−−−−−−−−−−−−−
-20 parts clay ・−・−−−−−・・
-・70 parts white carbon・----1---・・
-... 10 parts or more are mixed uniformly, and the active ingredient is 20%.
Obtain a powder.

1剋■工 Granules Compound of the present invention -・-・-11----------------------
・ 5 parts bentonite −・−・−1−−−・・
−・25 parts talc −・−・−1−−−
----1---- After uniformly mixing and pulverizing 70 parts or more, a small amount of water is added, stirring and kneading is carried out, granulation is performed using an extrusion type granulator, and the mixture is dried to form granules.

Next, the usefulness of the compound of the present invention as a soil disease control agent will be specifically explained in the following test examples.

跋MJI Upper Cruciformaceae plant clubroot control test (emulsion treatment) Plastic pots with a diameter of 8o were filled with sterilized soil, and three rough seeds of Chinese cabbage (variety Nikin-sho No. 2) were seeded per pot. The emulsion shown in the formulation example was diluted to a predetermined concentration and 10 ml per pot was irrigated onto the surface of this pot. The day after treatment, the clubroot disease 11 of cruciferous plants (PI
The pot surface was inoculated with a suspension of dormant spores of the crucianaceae root gall fungus, which was obtained by homogenizing 1 g of Chinese cabbage root gall per pot, which was formed by infection with C. ssicae. This was placed in a glass greenhouse, Chinese cabbage was allowed to grow, and the state of root growth was investigated 5 weeks after inoculation, and the control value was calculated using the following formula.

Number of individuals in which root galls are not observed.

nl: Number of individuals with root galls growing only on supporting roots.

n8: Number of individuals in which root galls are attached to both the branch root and the main root, but are not very enlarged.

n,: Number of individuals with root galls growing on both the branch roots and the main root, which are significantly enlarged.

N: Total number of surveyed individuals.

PCNB hydrating agent (75% active ingredient) was used as a control drug.

The results are shown in Table 2.

Compounds in Table 2 are treated as active ingredients (Kg/ha)2
1 0.5 0.2 No, 4 100 100 80 5O
No, 5 100 100 91 55
No, 6 100 100 100 9
3No, 7 100 100 100
85No, 8 100 100 100
100No, 9 100 100 10
0 93 Comparative compound A 0000 Comparative compound B 30 0 0 0 Comparative compound C 806000 Comparative compound D 0000 Comparative compound E 0000 Comparative compound F 81 80 42 0 Comparative compound G 77 40 0 0 PC
NB 0 0 0 Q 2nd
Comparative compounds A to E in the table are compounds specifically described in JP-A-60-152401, and comparative compound F
and G are the compounds specifically described in JP-A No. 62-16465, and have the following structural formula (% formula %) PCNB is pentachlornitrobenzene and is a commercially available soil disease control agent having the following structure. .

W Cruciform plant clubroot control test (powder treatment) 180 g of sterilized soil and the compound of the present invention at 5%, 2%, 1%,
50m of each powder containing 0.5% and 0.2%
Mix well with g and pack into a/20000 bottles,
Three seeds of Chinese cabbage (variety: Kinsho No. 2) were sown per pot. On the day after treatment, 1 g of Chinese cabbage root galls formed by infection with Plass brassicae were homogenized per pot on the next day. was inoculated by irrigating the surface of the pot. This was placed in a glass greenhouse, Chinese cabbage was grown, and the state of root growth was investigated 5 weeks after inoculation, and the control value was calculated using the same method as in Test Example 1. However, 50 mg of PCNB powder (5% active ingredient) was used as a control drug.

The results are shown in Table 3.

Table 3 Compound Active ingredient processing amount (Kg/ha) 5 2
1 0.5 0.2No, 6 10
0 100 100 100 89No, 8
100 100 100 100 1
00No, 9 100 100 100
100 96 Comparative Compound C90755000 Comparative Compound F 100 90 80 30
0PCNB 0 0 0
0 0 (hereinafter referred to as blank space) Lame limbs Phytotoxicity test A plastic pot with a diameter of 8 cm was filled with sterilized soil.
Three Chinese cabbage seeds (variety: Yotoku No. 2) were sown per pot.

The emulsion shown in the formulation example was diluted to a predetermined concentration and 10-1 per pot was irrigated onto the soil surface of this pot. This pot was placed in a glass greenhouse, and 3 weeks after sowing, the presence or absence of chemical damage was visually observed.

The results are shown in Table 4.

(Hereinafter, blank space) Table 4 Compound Active ingredient processing amount (Kg/ha) No.
4 0 0 ONo, 5
0 0 ONo, 6 0 0
ONo, 7 0 0 ONo, 8
0 0 ONo, 9 0
0 0 Comparative Compound A 200 Comparative Compound B 5 2 1 Comparative Compound C521 Comparative Compound D 3 0 0 Comparative Compound E 4 0 0 The definitions of the data for O to 5 in Table 4 are as follows: 0.-
・-1111・Growth of the aboveground part is almost the same as that of the untreated area (almost no chemical damage is observed)
Approximately 5χ (some drug damage is observed) 2.---- Aboveground growth is approximately 71 to 80χ of the untreated area (some drug damage is observed) 3. 61~ in untreated area
Approximately 70χ (considerable chemical damage is observed) 4--------1.- Aboveground growth is untreated 50-6
0% or less (Significant chemical damage is observed) 5. Complete withering of plants (Significant chemical damage is observed.) Patent applicant: Nissan Chemical Industries, Ltd. Hodogaya Chemical Industry Co., Ltd.

Claims (6)

[Claims] (1) General formula (I): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) A benzamide derivative or those salts. (2) Benzamide derivatives or salts thereof according to claim 1, wherein X is a chlorine atom and n is an integer of 2. (3) The benzamide derivative or salt thereof according to claim 1, wherein X is a chlorine atom, n is an integer of 2, and the substitution positions of X are the 2nd and 4th positions. (4) General formula (I): ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) A benzamide derivative or A soil disease control agent characterized by containing at least one of these salts as an active ingredient. (5) The soil disease control agent according to claim 4, wherein the active ingredient is a benzamide derivative in which X is a chlorine atom and n is an integer of 2. (6) The soil disease control agent according to claim 4, wherein the active ingredient is a benzamide derivative in which X is a chlorine atom, n is an integer of 2, and X is substituted at the 2nd and 4th positions.