JPS6239563A - Beta-nitrophenethyl derivative and agricultural and horticultural germicide - Google Patents

Abstract

NEW MATERIAL:A compound expressed by formula I [R1 is H or lower alkyl; R2 is alkyl, hydroxy, amino, alkoxycarbonyl, phenyl, benzyl, naphthyl, etc.; X is H, halogen, hydroxyl, nitro, (halogen-substituted) lower alkyl, lower alkoxy, etc.; n is an integer 1-3]. EXAMPLE:2-(p-Chlorophenylthio)2-phenyl-1-nitroethane. USE:A safe agricultural and horticultural germicide effective for loose smut of wheat or barley, etc., and blast or rice plant, etc., when used as a seed disinfectant without toxicity to humans, animals and fishes. PREPARATION:According to the reaction formula, a beta-nitrosonitroethane expressed by formula II is reacted with a mercaptan expressed by formula III to afford the aimed beta-nitrophenethyl derivative expressed by formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to a novel β-nitro7enethyl derivative and an agricultural and horticultural fungicide containing the same as an active ingredient.

Conventional techniques and problems Conventional β-nitrophenethyl derivatives are known to have physiological activity as medical bactericidal agents and antitumor agents [for example, Journal of the American
Chemical Society (J, Am, Ohem, Soc
,], 22j, /41 λ -1 (/ri!l) and the same magazine, 77.3140 (/F!jr)].

For agricultural use, there is only a report on its acaricidal activity [Chemical Abstracts, LO, 1AO4/c(/94&)], and there are no reports on its usefulness or possibility as an agricultural fungicide.

A large number of compounds have been known or actually used as fungicides for agriculture and horticulture, but the use of one compound is not effective in controlling all plant pathogens, and the antibacterial spectrum is wide and narrow. They vary and may not be completely satisfactory. There is a problem that bacteria that were initially effective will acquire full resistance and become ineffective. Furthermore, some conventional fungicidal compounds exhibit phytotoxicity, and even those that do not initially exhibit phytotoxicity have problems such as the generation of drug W as a result of accumulation in the soil due to long-term application. For this reason, there is a constant need to develop and provide new fungicides for horticulture.

Means for Solving Problems 1 Action and Effect The present inventors intend to develop a new fungicide that can solve the various problems faced in the field of agricultural and horticultural fungicides as described above.
Focusing on β-nitrophenethyl derivatives, we discovered a large number of compounds of this type and intensively investigated their practicality in the field of horticulture.As a result, we found the general formula (I):
(In the formula, R1 represents a hydrogen atom or a lower alkyl group; R2 is an alkyl group, hydroxy-, amino-.

Alkoxycarnyl, alkoxyrudenyloxy, alkylcarzenyloxy, triphenyloxy, penzoyloxy, phenoxycarbunyloxy
l'! Tri-lower alkyl, bovine sicily, substituted lower alkyl, halogen, amino, alkyl.

a phenyl group optionally substituted with a substituent selected from halogen and nitro groups, a benzyl group optionally substituted with a halogen, a naphthyl group, a cyclohexyl group, a biIJmidinyl group, N,N-dilower alkylthiocarbamoyl (on the group or phenyl nucleus) may be substituted with -rogen or lower alkyl/-phenyl ditroethane-/
-yl 7i f 9: Xtfi hydrogen atom, norogen atom, hydroxyl group, nitro group, lower alkyl group optionally substituted with halogen, lower alkoxy group, lower alkoxycarzenyl group, dialkylamino group 17'
cH represents a benzyloxy group which may be substituted with halogen; n represents an integer from t to 3;
- It has been found that nitrophenethyl derivatives exhibit unexpectedly excellent efficacy as agricultural and horticultural fungicides and are useful for solving the above-mentioned problems.

The gist of the first invention is therefore a novel β-nitrophenethyl derivative represented by the general formula (I) and particularly useful as a fungicide for agricultural and horticultural purposes.

The second aspect of the present invention resides in an agricultural and horticultural pesticide containing the derivative as an active ingredient.

In the definition of the general formula (r) above, the term -lower l used for an alkyl group or an alkoxy group is generally /,
Indicates that it contains J carbon atoms.

Therefore, preferred specific examples of lower alkyl groups are:

) Chi, :f-chill, n-propyl,! -Propyl.

n-butyl, 5ec-butyl, i-butyl* tar
Includes t-butyl, n-pentyl, n-hexyl, i-hexyl groups, and the like. Preferred specific examples of the lower alkoxy group include methoxy, ethoxy, n-propoxy, i-
Propoxy, n-butoxy, i-butoxy, 5ee-
Includes butoxy, tert-butoxy, n-pentyloxy groups, and the like.

Next, representative examples of the β-nitro7enethyl derivatives of the present invention are shown in Table 1 along with their physical properties. The outline and specific examples (Examples) of the methods for producing these chemical compounds will be described later. tx compound is also referred to in the Examples and Test Examples below.

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D. The β-nitro 7enethyl derivative represented by the general formula (I) according to the present invention can be easily produced by a novel method of reacting β-nitrosonitroethanes with mercaptans as shown in the following reaction formula (1). be able to.

This reaction proceeds suitably in a polar solvent such as ethanol, acetonitrile, or chloroform by adding a catalytic amount of triethylamine or pyridine. - The reaction temperature is not particularly limited, but is preferably room temperature to 10°C, and the reaction is completed in Q, 7 to 3 hours.

The compound of the present invention can also be attached by a known method (for example, JP-A-32-93730) in which mercaptans are added to a β-nitrostyrene derivative according to the following reaction formula Q).

Next, all representative examples of the production of the compound of the present invention will be further explained.

Example / 2- (p-chlorophenylthio-2-phenyl-1/
-Synthesis of nitroethane (compound 1i/compound) Cornitrone-Cophenyl-t-nitroethane t t
, Ot (0,t Omolino acetonitrile s.

mtVcR, p-chlorothiophenol/! ,j
9(o,io) was added dropwise, followed by 72 drops of pyridine, and the mixture was stirred at room temperature for 3 hours.

Then, the solvent was distilled off under reduced pressure to obtain the title compound as a pale yellow oil.

Collection f, j P (2-nitrofucophenyl-
Yield based on l-nitroethane P Tatino: n”/,
6216 Example λ-(Hydroxyethylthiono-2-phenyl-l-nitroethane)
(Dissolved in 010 mol acetonitrile λ00-,
Mercaptoethanol 4'Of (031 mol) was added. Then, 3 drops of triethylamine were added, and 4 to
The mixture was heated and stirred at , zo°C for 20 minutes.

After cooling, the solvent was distilled off under reduced pressure to obtain the title compound as a pale yellow oil.

Yield//Jf (Yield Quantitative F: n25/jjA & Example 3 27 (,-Chlorphenyl)-2-()Toxical?
Nylmethylthio)-/-Nitroethane (chemical compound of Chemical Taki 55) -2-(o-chlorophenyl-2-2)l:2:/-
/-Nido Oeta 70.7jf (,0,OOJ!Moni) to acetonitrile! -, thioglycolic acid methyl ester 00.3 I P (0,00 J j mol) was added dropwise, 1 drop of triethylamine was added, and 2
．． After stirring for 3 hours, the mixture was treated in accordance with Example 1 to obtain the title compound gold as a pale yellow oil.

Yield i%/, (7? (Yield relative to 2-(o-chlorophenylnorconitroso-nitroethane, 25 tata%, n/,!)
! P! Example Synthesis of f/-(P-chlorophenyl)-7-C hydroethylthione-co-nitroethane (compound of compound Nα116) p-chloro-β-methyl-β-nitrostyrene 2.00
? (0,0/0 mok) f dissolved in 10-methanol, 0.71 t mercaptoethanol
10 mol) followed by triethylamine/drops k
The mixture was stirred for 10 minutes at 30°C to Hiroo°C, and then at room temperature for 2 hours. Then treated according to Example 1.

The title compound was obtained as a pale yellow oil.

Yield tλ, 7 P (yield to p-ri-o-β-methyl-β-nitrostyrene P44): n Ij6/7
Example! co(p-7'romphenylthionoko<p-methylphenyl)-/-nitroethane<carbohydrates lμ7's base p-methyl-β-nitrostyrene-,/2 f (,0
,0/J molno dissolved in acetonitrile j-.

η-promthiophenolco, μj? (θ, 0/J
Morno and triethylamine/@ were added dropwise, and the mixture was stirred at room temperature for 3 hours. Then processed according to Example 1 and #!
A yellow oily compound was obtained.

Accommodation t4', -? f (yield based on p-methyl-β-nitrostyrene H) e n 22/ j -2-24t
The novel β-2) a7 of the present invention represented by general formula (1)
Enethyl derivatives are #! As an agricultural and horticultural fungicide, it exhibits superior 2'Lrc bactericidal activity compared to many known agricultural and horticultural fungicidal additives. Namely, one compound of the present invention is.

Used as a seed disinfectant to treat smut on wheat.

It exhibits an antiseptic effect on rice smut, and has particularly excellent disinfecting effects against rice sesame leaf blight and rice blight.

It also shows control effects against other plant diseases. For example, grains include rust and powdery mildew in wheat, sesame leaf blight in rice and corn, and rice blast; pulses include rust in soybeans and broad beans, and anthrax in kidney beans; vegetables include cucumbers, watermelons, and eggplants. .

It is effective against powdery mildew on green peppers, anthrax and vine blight on cucumbers, watermelons, and melons, and mildew on green onions. In addition, in orchards, Phosphorus 2's red star blight, black star blight,
It is effective against powdery mildew, pear blight, black blight, pear blight, late rot, and powdery mildew. Furthermore, although the compounds of the present invention have strong antibacterial effects, they hardly cause any phytotoxicity to useful plants and can be used safely without toxicity to animals or fish.

Specifically, the agricultural and horticultural fungicide according to the second invention is prepared by using the compound of general formula (1) as it is or diluting it with a liquid carrier such as water or an organic solvent, a solid powder carrier, or other suitable carrier. If necessary, add auxiliary agents such as wetting agents, spreading agents, dispersants, emulsifiers, and fixing agents to create irrigation agents, oil agents,
It may be used in formulations such as liquids, emulsions, sol (flowable) formulations, granules, DL (P liftless) type powders, fine granules, powders, etc. Liquid carriers used in formulation include, for example, water, Solvents such as aromatic hydrocarbons, aliphatic hydrocarbons, alcohols, esters, ketones, acid amides, and dimethyl sulfoxide can be used.Solid carriers include clay, talc, kaolin, bentonite, diatomaceous earth, Examples include mineral powders such as calcium carbonate and silicic acid, and organic powders such as rice flour.Auxiliary agents include nonionic, anionic, cationic, and amphoteric surfactants, and ligninsulfonic acid or its salts. , gums, aliphatic salts, methyl cellulose, and other glues can be used.

Preparations such as irrigation agents, solutions, and emulsions have an activity level of 1-
It may be contained in an amount of 7j% by weight, usually in a range of 2 to 73% by weight. These formulations are generally diluted with water to a concentration of 0.000/
−/Used at 0% by weight. Furthermore, granules, microgranules and powders generally contain an active fraction of θ, /-/0 wt'It%. In addition, concentrated liquids such as oils, emulsions, and sols (flowables) can be used as they are as micro-dose dispersants without being diluted. Furthermore, in order to use it as a seed disinfectant, it is effective to coat crop seeds with an irrigation agent or powder as is, or to dilute the irrigation agent, sol, emulsion, etc. with water and immerse the seeds. It is.

Furthermore, when using the compound of the present invention as a fungicide for agriculture and horticulture, it is possible to expand the applicability by mixing with insecticides, fungicides, herbicides, plant growth regulators, etc. A synergistic effect can also be expected by using these in combination.

A specific example of formulation of the agricultural and horticultural fungicide of the present invention will be explained using a T-bag example, but the present invention is not limited to these examples. It should be noted that all references to "Example Middle" indicate parts by weight.

Compound 20 parts of the compound flattened, polyoxyethylene alkylaryl ether! 1 part, lignin sulfone liquid lucium, 3 parts, and 72 parts of diatoms are uniformly ground and mixed to obtain an irrigation agent containing 20% of the active ingredient.

Example 7 Emulsion 30 parts of Compound 4444, 20 parts of xylene sO and 20 parts of polyoxyethylene alkylaryl ether are uniformly dissolved and mixed to obtain an emulsion containing 30 parts of the active ingredient.

50 parts of compound 1621 and 10 parts of ethyl cellosolve
Parts are evenly dissolved and mixed to obtain the active content! Obtain an oil solution containing 0.

Compound I of compound JpFLirt ground to less than ioμ
IQ part, lauryl sulfate λ part, 2 parts of sodium alkylnaphthalene sulfonate, 1 part of hydroxypropyl cellulose, and jj parts of water are mixed uniformly to form the active ingredient≠
A sol containing Q% is obtained.

Compound 4ir/part, silicic anhydride fine powder 0.37
1 part of calcium stearate, 10 parts of clay, and 1 part of talc were uniformly mixed and ground to obtain 1 part of the active ingredient.
Obtain a powder containing %.

Example II Granules 3 parts of Compound A/Li 1, 1 part of calcium lignin sulfonate, 30 parts of bentonite and 6 parts of clay were uniformly mixed and pulverized, water was added and granulated, dried and sieved. Granules containing 3% of active ingredient are obtained.

Next, the usefulness of the compound of the present invention as an agricultural and horticultural fungicide,
Specific examples of the effects are shown in Test Examples/and .

Test Example 1 Rice Bakakyo Seed Disinfection Effect Test Rice (Quality:
Kinki No. 33] during the flowering period, the rice baka-nae disease fungus (Fusarium
The test rice was paddy infected with the rice bacterium bacterium, which was obtained by spray inoculation with a concentrated spore suspension of M. moniliform. For seed disinfection, a diluted solution with a predetermined concentration is prepared using a hydrating powder prepared according to Example B, and the amount ratio (v/v) of the chemical solution to the above rice seeds is f/l.
It was immersed and sterilized at 20°C for 2 hours. After sterilizing the seed rice, soak it at 20℃ for 3 days, germinate 4 J4c seeds at 30℃, and put the pigeon-breasted seed rice into Kumiai granular culture medium (Kureha Kagaku Kogyo Co., Ltd. M) according to the box cultivation method. Sowed. After that, they were cultivated in a glass greenhouse.

To investigate the onset of the disease, remove the entire surface of each treatment plot 1 day after sowing (Koha stage), and investigate the number of bacteria that cause the rice baka seedling disease to identify 100 infected plants (
The control value (@fcn) was calculated from this. This test was conducted in triplicate per section, and the average seed disinfection rate (%) was determined. In addition, the chemical damage to rice was investigated using the indicator of lack of control. did.

The results are shown in Table 1.

Investigation indicators for drug damage! : Extremely severe Hiroshi: Extremely 3: Many ノ: Slightly l: Slightly O
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The commercially available drug 4nomyl [methyl/-(butylcarbamoyl)-nobenzimidazole carcemade] is shown.

Test Example No. Rice Sesame Leaf Blight Seed Disinfection Efficacy Test Rice sesame leaf blight was frequently observed in the field, and paddy infected with the naturally infected rice sesame leaf blight fungus (Cochriozerus myabeanus) was collected and used as test rice.Seed disinfection The method and other operating procedures were the same as in Test Example 1.

The disease onset investigation was carried out 10 days after sowing, and the number of bacteria causing rice sesame leaf blight was investigated, and the seed disinfection rate (@) was calculated in the same manner as in the rice blight seed disinfection effect test. Test Example 1
The chemical damage was investigated using the same criteria.

This test was conducted in three consecutive sessions per section, and the average seed disinfection rate (%)
I asked for The results are shown in Table 3.

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(Note) Commercially available drug Isolo Dione (3-(J.

! --)chlorophenyl)-N-isozorovir-2,≠
-dioxoimidazolidine-l-carzexamide].

Claims (1)

[Claims] 1. General formula: ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R_1 represents a hydrogen atom or a lower alkyl group; R_2 represents an alkyl group, hydroxy-, amino-, alkoxycarbonyl- , alkoxycarbonyloxy-
, alkylcarbonyloxy-, triphenyl-, benzoyloxy-, phenoxycarbonyloxy- or tri-lower alkoxysilyl-substituted lower alkyl group, phenyl optionally substituted with a substituent selected from halogen, amino, alkyl and nitro groups. group, benzyl group, naphthyl group, cyclohexyl group, pyrimidinyl group, N,N-di-lower alkylthiocarbamoyl group, or 1-phenyl which may be substituted with halogen or lower alkyl on the phenyl nucleus 2 −
represents a nitroethane-1-yl group; X is a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a lower alkyl group optionally substituted with halogen, a lower alkoxy group,
A β-nitrophenethyl derivative represented by a lower alkoxycarbonyl group, a dialkylamino group, or a benzyloxy group which may be substituted with halogen; n represents an integer of 1 to 3. 2. As an active ingredient, the general formula: ▲Mathematical formula, chemical formula, table, etc.▼ (In the formula, R_1 represents a hydrogen atom or a lower alkyl group; R_2 represents an alkyl group, hydroxy-, amino-, alkoxycarbonyl-, alkoxy carbonyloxy
, alkylcarbonyloxy-, triphenyl-, benzoyloxy-, phenoxycarbonyloxy- or tri-lower alkoxysilyl-substituted lower alkyl group, phenyl optionally substituted with a substituent selected from halogen, amino, alkyl and nitro groups. group, benzyl group, naphthyl group, cyclohexyl group, pyrimidinyl group, N,N-di-lower alkylthiocarbamoyl group, or 1-phenyl which may be substituted with halogen or lower alkyl on the phenyl nucleus 2 −
represents a nitroethane-1-yl group; X is a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a lower alkyl group optionally substituted with halogen, a lower alkoxy group,
An agricultural and horticultural product characterized by containing a β-nitrophenethyl derivative represented by a lower alkoxycarbonyl group, a dialkylamino group, or a benzyloxy group which may be substituted with halogen; n is an integer of 1 to 3. disinfectant.