JPS62174063A - Triazole derivative, plant growth regulator and agricultural and horticultural fungicide comprising same as active ingredient - Google Patents

Abstract

NEW MATERIAL:A compound shown by formula I (X and Y are halogen, lower alkyl or nitro; m and n are 0-2; m+n = 0-2; R1 is lower alkyl, hydroxymethyl or acetoxymethyl; R2 is H, lower alkyl or acetyl; with the proviso that R2 is H, lower alkyl, etc., when Xm is 4-Cl, n is O and R1 is CH3). EXAMPLE:A compound shown by formula I when Xm is 4-Cl, Yn is H, R1 is CH3 and R2 is H. USE:A plant growth regulator and an agricultural and horticultural fungicide. Usable for lodging prevention or growth suppression of grain such as rice plant, wheat, etc., and crops such as soybean, cotton, etc. PREPARATION:A triazole compound shown by formula II (R1' is lower alkyl or acetoxymethyl; R2' is lower alkykl or acetyl) is reacted with a reducing agent such as NaBH4, etc., in a solvent such as methanol, etc., at -20-40 deg.C for 0.5-6 hours and treated with an alkali aqueous solution or acidic aqueous solution to give a compound shown by formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to a plant growth regulator and an agricultural and horticultural fungicide containing a novel triazole derivative as an active ingredient.

<Prior Art> Triazole compounds of the following types are used to treat plant growth. <Problems to be Solved by the Invention> However, the above-mentioned compounds are not necessarily sufficient as plant growth regulators and agricultural and horticultural fungicides. isn't it.

<Means for Solving the Problems> In view of the above-mentioned situation, the present inventors have conducted intensive studies on the plant growth regulating action and the bactericidal action for agricultural and horticultural purposes of triazole compounds, and have developed a triazole represented by the following general formula. It was discovered that the derivative has an excellent plant growth regulating effect and a bactericidal effect for agricultural and horticultural purposes, leading to the present invention.

That is, the present invention is based on the general formula (wherein X and Y are the same or different and represent a halogen atom, a lower alkyl group, or a nitro group, m,
n each represents 0°1 or 2, and the sum of m and n represents 0°1 or 2, R1 represents a lower alkyl group, hydroxymethyl group or acetoxymethyl group, R represents a hydrogen atom, Represents a lower alkyl group or an acetyl group. However, when Xm is a 4-chloro atom, n is 0, and R1 represents a methyl group, R2 represents a hydrogen atom or a lower alkyl group, and Xm is a 2,4-dichloro atom, n is 0, and R1 is When representing a methyl group, R
2 represents a lower alkyl group or an acetyl group. The present invention provides a triazole derivative represented by the following formula and a plant growth regulator and a fungicide for agricultural and horticultural use, which are characterized by containing the triazole derivative as an active ingredient. Note that the compound of the present invention has optical isomers, and the present invention includes them.

The compound of the present invention has, for example, the general formula, R1' represents a lower alkyl group or an acetoxymethyl group, and Rf represents a lower alkyl group or an acetyl group. ) It can be produced by treating the triazole compound represented by the following with a reducing agent and then treating it with an alkaline aqueous solution or an acidic aqueous solution.

In the above production method, examples of reducing agents used in the reduction reaction include lithium aluminum hydride,
Examples include sodium borohydride, sodium cyanoborohydride, diborane, and the like. At this time, the amount of reducing agent used in the reaction is 0.25 xane, heptane, ligroin, aliphatic hydrocarbon such as petroleum ether, benzene, toluene,
Aromatic hydrocarbons such as xylene, ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, diethylene glycol dimethyl ether, methanol, ethanol, isopropanol, t-butanol, octatool, cyclohexanol, methyl cellosolve, diethylene glycol, glycerin, etc. Alcohol, nitriles such as acetonitrile and isobutyronitrile, pyridine, triethylamine, tertiary amines such as N,N-diethylaniline, tributylamine, N-methylmorpholine, formamide, N,N-dimethylformamide, acetamide Sulfur compounds such as dimethyl sulfoxide and sulfolane, liquid ammonia, water, etc., or mixtures thereof may be mentioned.

In addition, the reaction temperature and reaction time are usually -20 to 4
The purpose can be sufficiently achieved within the range of 0°C, preferably -10°C to room temperature, and for 0.5 to 6 hours.

After completion of the reaction, the compound of the present invention can be obtained by treatment with an alkaline or acidic aqueous solution and, if necessary, purification by chromatography, distillation, recrystallization, etc.

In the above production method, when R1' of the triazole compound represented by general formula (1) represents an acetoxymethyl group, or when Ri represents an acetyl group, after the reaction is completed, the reaction product is diluted with alkaline water. When processed,
A compound of the present invention represented by the general formula (1) in which the substituent R1 is a hydroxymethyl group or R2 is a hydrogen atom is obtained.

When producing the compound of the present invention, the compound represented by the general formula (1), which is a raw material compound, is 1.0 ~1.1 equivalent of benzaldehyde represented by the general formula (wherein, X, Y, m, and n have the same meanings as above) in a solvent,
．． 1 at 80-140°C in the presence of 0 equivalents of alkaline catalyst.
It can be produced by reacting for ~12 hours.

Solvents used include acetic anhydride, benzene, toluene,
Examples include xylene, acetonitrile, methanol, and ethanol. As an alkali catalyst, potassium carbonate,
Examples include sodium carbonate, pyridine, triethylamine, sodium methylate, sodium acetate, sodium hydroxide, potassium hydroxide, and the like.

After the reaction is completed, a usual post-treatment is performed to obtain a triazole compound represented by the general formula (1).

Incidentally, the compound represented by the general formula (2) is manufactured by a known manufacturing method.

The compounds of the present invention can be used to prevent lodging or suppress elongation of grains such as rice, wheat, barley, and rye, and crops such as soybean and cotton. It can also be used to suppress the growth of lawns, suppress the growth of overhanging branches of fruit trees, increase the commercial value of ornamental plants by reducing their clumps, suppress the growth of hedges, and adjust the flowering period.

Furthermore, the compounds of the present invention have preventive, therapeutic, or systemic control effects against many plant diseases.

The target plant disease for which the compound of the present invention exhibits an excellent control effect is powdery mildew of wheat (Erysphe gram).
inis f, sp, hordei, f, sp
, triti-ci), rust (Puccinia
striiform is, P, gram 1-n
is, P, recondita, P, horde
i), naked smut (Ustilago tritici,
U, nuda), eyespot (P5eudo)
cercosporella herpotr 1ch
oides), Rhynchosporium
5ecalis), leaf blight (Septo-ria
tritici), Blight (Leptosphaeri)
a nodorum), fruit rot disease (Penicill
ium digitatum, P, ita-1ic
um), powdery mildew of apples (Podosphaer
aleucotricha), Ventur
ia 1naequalis), Nasinoscota (Ven
Turia nashicola), Gymn.
osporangium haraeanum), peach sclerosis (Sclerotinia cinerea)
), grape powdery mildew (Uncinvla neca
tor), rust (Phakopsoraampelo
psidis), powdery mildew of cucurbits (S phae-
rotheca fuliginea), tomato leaf mold (C1a-dosporium fulvum)
, powdery mildew of eggplant (Erysiphe cichor)
acearum), white spot disease of cruciferous vegetables (Cerc
osporel la brassicae), onion rust (Puccinia allii), groundnut black astringency (Mycosphaerella per
sonatum), Cerco-spora
arachidicola), powdery mildew of pea (
Erysiphe pisi), powdery mildew of strawberries (Sp-haerotheca humuli), Exob-asidium retic of tea
ulatum), Elsinoeleucos
pi la), tobacco powdery mildew (Erysiphe
cichoracearum), brown spot of sugar beet (
Cercos-pora beticola), rose scab (D 1plocarponrosae),
Powdery mildew (S phaerotheca panno)
sa), Puccinia hori
ana), Botrytis on various crops
S cinerea), Sclerotini
a sclerotiorum).

Therefore, the compound of the present invention can be used in rice fields, fields, orchards, tea plantations,
It can be used as an active ingredient in plant growth regulators for pastures, lawns, etc., and fungicides for agriculture and horticulture.

The compound of the present invention is usually carried on a solid carrier, a liquid carrier, or a surface active carrier.
It is used by mixing with sex agents and other formulation auxiliaries to formulate emulsions, wettable powders, solutions, suspensions, granules, etc. The above formulations generally contain the compound of the present invention as an active ingredient in an amount of 0.05 to 95% by weight, preferably 0.1 to 80% by weight.

Examples of the solid carrier include fine powders or granules such as kaolin clay, attapulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, Kuru powder, urea, ammonium sulfate, and synthetic hydrous silicon oxide. Examples of liquid carriers include aromatic hydrocarbons such as xylene and methylnaphthalene, isopropanol,
Alcohols such as ethylene glycol and cellosolve; ketones such as acetone, cyclohexanone and isophorone;
Examples include vegetable oils such as soybean oil and cottonseed oil, dimethyl sulfoxide, acetonitrile, and water.

Surfactants used for emulsification, dispersion, wet spreading, etc. include alkyl sulfate salts, alkyl (aryl)
Anionic surfactants such as sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkylaryl ether phosphate salts (1B), polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene polyoxypropylene blocks Examples include nonionic surfactants such as copolymers, sorbitan fatty acid esters, and polyoxyethylene sorbitan fatty acid esters.

As formulation adjuvants, lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC
(carboxymethylcellulose), PAP (isopropyl acid phosphate), and the like.

These preparations can be used as they are or diluted with water, etc., and treated with foliage or soil. For soil treatment, the formulation is either spread on the soil surface (if necessary, mixed with the soil after application) or irrigated into the soil. It can also be used in combination with insecticides, acaricides, nematicides, other fungicides, herbicides, fertilizers, soil conditioners, etc., if necessary.

The application U of the compound of the present invention varies depending on weather conditions, soil conditions, formulation form, mixing ratio of active ingredients, type of target crop, etc., but is generally 0.05 to 50 y per are, preferably o, i to 20 g. Yes, emulsions, wettable powders, liquid preparations, etc. should be diluted with 1 to 20 liters of water per are (adding a spreading agent such as a spreading agent if necessary) and applied.
Granules etc. are applied as is without any dilution.

In addition to the above-mentioned surfactants, the spreading agents include polyoxyethylene resin acid (ester), lignin sulfonate,
abietate, dinaphthylmethane-disulfonate,
Examples include paraffin.

<Examples> The present invention will be explained in more detail below with reference to Examples, Formulation Examples, and Test Examples.

Example 1 (Production of compound (4) of the present invention) General formula (I
The compound represented by I) (XIT1=4-C1, Yn=H
9R1'=CHa, Rf=acetyl) 1.1F at 5vi
1 of methanol, 65q of sodium borohydride was added under water cooling, and the mixture was stirred for 8 hours. After completion of the reaction, 10st/water was added to the reaction mixture, and the residue was recrystallized from hexane:acetone (5:1) to obtain the compound of the present invention represented by the general formula (1) (Xm=4-Cl, Yn= H,R,=
CH,, R1=H) 500 Wg was obtained. Melting point 118-1
19°C Example 2 (Production of compound (16) of the present invention) Compound represented by the general formula (Xm=2CCYn=4
Cl-Rr=CHa* R4=CH5) 1. O
f was dissolved in 5 ml of diethyl ether, 50 q of lithium aluminum hydride was added under water cooling, and the mixture was stirred for 2 hours.

After the reaction is complete, add 10-diluted hydrochloric acid to the reaction mixture,
Stir for 1 minute and apply acetic acid ethyl chromatography (elution solvent;
The compound of the present invention represented by the general formula (I) was purified with toluene:acetone (8:1) (Xm=2-C1, Yn=4-C
1°R,=CH,,R,=CH,) 650 # was obtained.

Melting point: 91-92°C Table 1 shows the compounds of the present invention produced by the same method as above.

Next, examples of formulations of the compounds of the present invention will be shown. Parts are parts by weight.

Formulation Example 1 10 parts of compound (4), 8 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and 86 parts of synthetic hydrous silicon oxide are thoroughly ground and mixed to obtain a wettable powder.

Formulation Example 2 10 parts of compound (16), 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 70 parts of xylene are thoroughly mixed to obtain an emulsion.

Next, test examples will be given to specifically explain the plant growth inhibiting and fungicidal effects of the compounds of the present invention.

Test Example 1 Wheat Plant Height Elongation Suppression Test A 500 ml plastic pot was filled with sandy loam and 5 grains of wheat were sown. The grains were cultivated in a glass room, and after 14 days, when the wheat reached the two-leaf stage, a wettable powder obtained according to Formulation Example 1 was diluted with water so that the active ingredient reached a predetermined concentration.
Five liters of foliage was treated per pot. After the treatment, the wheat was cultivated for another 8 weeks and the height of the wheat plants was measured.

The test was conducted using two pots per treatment area.

The results are shown in Table 2. In addition, the numbers in the table are wheat 10
It is expressed as an index (%) when the average value of plant height is set as 100 for the untreated area.

Table 2 Comparative Control Compound A Test Example 2 Soybean Plant Height Suppression Test A 115,000 are Wagner pot was filled with sandy loam soil.
8 soybeans were mixed with tMMA1. This was cultivated in a glass room, and after 10 days, when the first soybean leaves had developed, the wettable powder obtained according to Formulation Example 1 was diluted with water to a predetermined concentration of 5 ml per pot. The stems and leaves were treated. After the treatment, the soybeans were cultivated for another two weeks and the plant height of the soybeans was measured. The test was conducted using two pots per treatment area. The results are shown in Table 8.

In addition, the numerical values in the table are shown as an index (%) when the average value of the plant height of six dice is set as 100 for the untreated plot.

Table 8 Test Example 8 Powdery mildew control test (preventive effect) Plastic pots were filled with sandy loam, wheat was sown, and the seeds were placed in a greenhouse for 1 hour.
It was grown for 4 days. A test compound prepared as an emulsifier in accordance with Formulation Example 2 was diluted with water to a predetermined concentration, and sprayed on the foliage of wheat seedlings with the third leaf developed so as to sufficiently adhere to the leaf surface. After spraying, the plants were grown in a greenhouse for 7 days, and inoculated with a spore suspension of powdery mildew by spraying and attaching agar pieces containing bacteria. After inoculation, the plants were grown at 28°C for 7 days and their control efficacy was investigated. The results are shown in Table 4.

In addition, the control efficacy is evaluated by visually observing the disease state of the test plant at the time of II'lE, that is, the degree of bacterial flora and lesions on leaves, stems, etc., and if no bacterial flora or lesions are observed, it is rated as 5 or 10. If about 80% of gt' is observed, it is ``4'', if about 80% of gt' is observed, it is ``8'', if about 50% of gt' is observed, it is ``2'', and if about 70% is observed, it is ``1''. If no difference from the disease onset condition is recognized, it is evaluated as "0" and evaluated on a 6-level scale from 0 to 5, and indicated as 0.1.2.8.4.5.

Table 4 Comparative Control Compounds <Effects of the Invention> The triazole derivatives of the present invention have excellent plant growth regulating effects and bactericidal effects for agricultural and horticultural purposes, and are effective as plant growth regulators and horticultural fungicides. .

(27 completed)

Claims (2)

[Claims] (1) General formula ▲ Numerical formula, chemical formula, table, etc. 2
, and the sum of m and n represents 0, 1 or 2,
R_1 represents a lower alkyl group, a hydroxymethyl group or an acetoxymethyl group, and R_2 represents a hydrogen atom, a lower alkyl group or an acetyl group. However, Xm
is a 4-chloro atom, n is 0, and R_1 is a methyl group, R_2 is a hydrogen atom or a lower alkyl group, and Xm is a 2,4-dichloro atom, n is 0, and R_1 is a methyl group. When R_3 represents a lower alkyl group or an acetyl group. ) A triazole derivative represented by (2) General formula ▲ Numerical formula, chemical formula, table, etc. 2
, and the sum of m and n represents 0, 1 or 2,
R_1 represents a lower alkyl group, a hydroxymethyl group or an acetoxymethyl group, and R_2 represents a hydrogen atom, a lower alkyl group or an acetyl group. However, when Xm is a 4-chloro atom, n is 0, and R_1 represents a methyl group, R_2 represents a hydrogen atom or a lower alkyl group, and Xm is a 2,4-dichloro atom, n is 0, and R_1 is When representing a methyl group, R_2 represents a lower alkyl group or an acetyl group. ) A plant growth regulator and a fungicide for agricultural and horticultural use, characterized by containing the triazole derivative represented by the following as an active ingredient.