JPH013183A - Fused heterocyclic compounds, their production methods, and herbicides containing them as active ingredients - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to a novel fused heterocyclic compound, a method for producing the same, and a herbicide containing the same as an active ingredient.

<Prior art> Until now, US Pat. No. 4,188,487 has a
-methoxycarbonylphenyl)-5-methyl-5-isopropylimidacilin-4-one is also
Publication No. 24864 describes that 2-(8-propoxycarbonylpyridin-2-yl)-5-methyl-5-isopropylimidacilin-4-one can be used as an active ingredient of herbicides.

<Problems to be Solved by the Invention> However, these compounds are not necessarily satisfactory because their herbicidal efficacy is insufficient or their selectivity between crops and weeds is poor.

<Means for Solving the Problems> In view of the above situation 1, the present inventors conducted various studies and found that -par["I'] [In the formula, R1 and R2 are the same or different, and hydrogen represents an atom or a lower alkyl group, R3 is a lower alkoxy group,
It represents a lower alkyl group, phenyl group or halophenyl group, and Z represents CH or a nitrogen atom. ] The fused heterocyclic compound C shown below is referred to as the compound of the present invention. ) was found to be a compound having excellent herbicidal efficacy with few drawbacks as mentioned above, and exhibiting great selectivity between crops and weeds, and the present invention f was achieved.

Next, the method for producing the compound of the present invention will be explained.

The compound of the present invention is -per(n) [wherein R1, Rff and Z represent the same meanings as above, and R4 represents a lower alkyl group. ] An imidazolinone compound represented by the general formula C1)r)X
CH, COR5 (III) [wherein R3 represents the same meaning as above, and X represents a chlorine atom or a bromine atom. ] in the presence of a base.

In this reaction, the amount of the reaction reagent used is usually 1.0 to 1 equivalent of the imidazolinone compound represented by -per [■], and the amount of the compound represented by -per [lI[].
1.2 equivalents, and the base is 2.0-2.2 equivalents. The temperature and time of the reaction are usually 0 to 100°C and 10 minutes to 10 hours. Examples of the base used include sodium hydride, potassium hydride, lithium diisopropynamide, and the like. Further, the reaction is typically carried out in a solvent, and examples of the solvent used include ethers such as tetrahydrofuran, diethyl ether, and dioxane;
Examples include aromatic hydrocarbons such as benzene, toluene, and xylene, dimethylformamide, dimethyl sulfoxide, and mixed solvents thereof. After completion of the reaction, the desired compound of the present invention can be obtained by performing conventional post-treatments such as extraction, concentration, and if necessary, recolumn chromatography.

The above reaction is represented by the general formula (IV) [wherein R1, R2, R3, R4 and Z have the same meanings as above. ] The intermediate can be isolated, and the compound of the present invention can be produced in two steps with isolation, or in one step without isolation.

Examples of the compounds produced as described above are shown in Table 1. The compounds of the present invention can be used to treat various weeds that are problematic in the treatment of foliage and soil in fields, such as grasshopper, buckwheat, huskweed, purslane, chickweed, whiteweed, blue-green grass, Japanese radish, Japanese radish, shepherd's purse, American hornwort,
Broad-leafed weeds such as Ebisu grass, Japanese commonweed, American gold deer, field pansies, field pansies, Japanese morning glory, American morning glory, Japanese bumbleweed, Western bindweed, Japanese staghorn grass, Hotokenoza, Japanese serpentine, Japanese Physalis, Japanese fir tree, Japanese fir, sunflower, barnyard grass, Japanese barnyard grass, Japanese foxtail grass, and other broad-leaved weeds. , weeds of the grass family such as snail grass, sycamore, sagebrush, oat, oat, seiban sorghum, sorghum, grass, and weeds of the family Asiatic family, such as dayflower,
It has a herbicidal effect against weeds of the Cyperaceae family, such as Cyperaceae and Cyperaceae.

When using the compound of the present invention as an active ingredient of a herbicide,
It is usually mixed with solid carriers, liquid carriers, surfactants, and other formulation auxiliaries to formulate emulsions, wettable powders, suspensions, granules, etc.

These preparations contain the compound of the present invention as an active ingredient in a weight ratio of 1 to 90%, preferably 1 to 80%.

Examples of solid carriers include fine powders or granules such as kaolin clay, attapulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, walnut powder, urea, ammonium sulfate, and synthetic hydrous silicon oxide. Examples of liquid carriers include aromatic hydrocarbons such as xylene and methylnaphthalene, and methane. Alcohols such as real alcohol, Impropatol, ethylene glycol, and cellosolve, ketones such as acetone, cyclohexanone, and inholon, vegetable oils such as soybean oil and cottonseed oil, and dimethic acid.
Examples include resulfoxide, acetonitrile, water, etc.

Surfactants used for emulsification, dispersion, wet layering, etc. include alkyl sulfate salts, alkytalearyl sulfonates, dialkyl sulfosuccinates, and polyoxyethylene alkyl sulfates. Anionic surfactants such as realyl ether phosphate salts, non-ionic surfactants such as polyoxyethylene alkyethers, polyoxyethylene alkylaryl ethers, polyoxyethylene polyoxypropylene block copolymers, nrubitan fatty acid esters, and polyoxyethylene sorbitan fatty acid esters. Examples of the ionic interface include lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC (carboxymethylcellulose), and PAP (isopropyl acid phosphate).

The compound of the present invention is usually formulated and applied to soil or foliage before or after the emergence of weeds. Soil treatment includes soil surface treatment, soil mixing treatment, etc. Stalk and foliage treatment includes treatment from above the plant body, as well as local treatment that treats only weeds to prevent them from adhering to crops.

In addition, by mixing it with other herbicides, it is expected that the herbicidal efficacy will be enhanced2.In addition, insecticides, acaricides,
It can also be used in combination with nematicides, fungicides, plant growth control agents, fertilizers, soil conditioners, etc.

In addition, the compound of the present invention can be used as an active ingredient of a herbicide for fields, orchards, pastures, lawns, forests, non-filed cultivated land, and the like.

When the compound of the present invention is used as an active ingredient of a herbicide, the treatment amount varies depending on weather conditions, formulation form, treatment time, method, location, target weeds, European crops, etc., but is usually per 1 are. 0.12-100 f, preferably 0
．． Emulsions, wetting agents, suspending agents, etc. are usually mixed with 1 liter to 10 liters of water per are (if necessary, auxiliary agents such as spreading agents are added). Granules and the like are usually processed as they are without any dilution.

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

<Example> Hereinafter, the present invention will be further explained in production examples, formulation examples, and test examples.
Although this invention will be explained in detail, the present invention is not limited to these examples.

First, a production example of the compound of the present invention will be shown.

Production Example 1 (Production of Compound (8) of the Present Invention) 5-Methyl-2
-(5-isopropyl-5-methyl-4-oxo-2-
Methyl imidacillin-2-yl)benzoate O,l 56
f (!: 0.091 F of methyl bromoacetate was dissolved in 571 ml of tetrahydrofuric acid, and 0.028 F of sodium hydride (oil base 60%) was added while stirring under water cooling. The reaction solution was heated at room temperature for 80 minutes, then heated. After stirring under reflux for 80 minutes, it was cooled, and 5 ml of water and then 10 g of chloroform were added.The aqueous layer was neutralized with 2N hydrochloric acid and extracted with chloroform.After drying the chloroform layer over anhydrous magnesium sulfate, The solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography to obtain the target compound 0.128F.

Yield: 69.4% Melting point: 151.6°C Production Example 2 (Production of Compound (4) of the Present Invention) 2-(5-isopropyl-5-methyl-4-oxo-2-imidacylin-2-i)nicotine 0.578 F of ethyl bromoacetate and 0.867 F of ethyl bromoacetate were dissolved in tetrahydrofuran 4
ml, and 0.084 f of sodium hydride (oil base 60%) was added while stirring under water cooling. After stirring the reaction solution at room temperature for 1 hour, 20 ml of ethyl acetate and LOyxl of sodium bicarbonate solution were added. The layer was separated with ethyl acetate, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to leave a 0.0% residue.
765F was obtained.

0.892F of the obtained residue and 0.46O of ethanol
f in 2d of tetrahydrofuran, and while stirring under water cooling, add 0.044f of sodium hydride (60% oily).
added. The reaction solution was further heated under reflux for 1 hour at room temperature.
After stirring for 0 minutes, the mixture was cooled, and 10w1 of water and then 20w1 of chloroform were added. The aqueous layer was neutralized with 2N hydrochloric acid and extracted with chloroform. After drying the chloroform layer over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography to obtain the target compound 0.218F.017.2 nD 1.5467 Produced in the same manner. The compounds obtained are shown in the $2 table.

Table 2 shows examples of formulations. The compounds of the present invention are indicated by compound numbers in Table 2. Parts are parts by weight.

Formulation Example 1 50 parts of the compound (1) of the present invention, 8 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of synthetic hydrous silicon oxide are thoroughly ground and mixed to obtain a wettable powder C.

Formulation Example 2 10 parts each of the compounds (1) to (17) of the present invention, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 70 parts of ethyl alcohol are thoroughly mixed to obtain an emulsion.

Formulation Example 8 2 parts of the compound (8) of the present invention, 1 part of synthetic hydrous silicon oxide, 2 parts of cesium lignosulfonic acid, 80 parts of bentonite, and 65 parts of kaolin clay were thoroughly ground and mixed, water was added, and the mixture was thoroughly kneaded. Thereafter, the mixture is granulated and dried to obtain granules.

Next, test examples demonstrate that the compounds of the present invention are useful as active ingredients of herbicides. The compounds used for comparison are indicated by compound symbols in Table 8.

Table 8 In addition, the herbicidal efficacy was determined by visually observing the degree of inhibition of budding and growth of the test plants during the survey, and was evaluated as "0" if there was no or almost no difference from when the compound was not tested. If the plant dies or its growth is completely inhibited, it is evaluated as "lO", and is evaluated on a scale of 11 from 0 to 1O, with a rating of 0.1.
．． 2.8.4.5.6.7.8.9, expressed in lO.

Test Example 1 Upland Stem and Leaves Treatment Test A cylindrical plastic pot with a diameter of 1Oα and a depth of 10 mm was filled with upland soil, and barnyard grass, oats, radish, and Japanese radish were sown and grown in a greenhouse for 10 days. Then, Formulation Example 2
The test compound was made into an emulsion according to the above, and a predetermined amount of the emulsion was diluted with water containing a spreading agent equivalent to 10 liters per 1 are, and the foliage was treated from above the plant using a small sprayer. 20 days after treatment
The plants were grown in a greenhouse for one day and their herbicidal efficacy was investigated. The results are shown in Table 4.

Table 4 Test Example 2 Upland Soil Treatment Test A cylindrical plastic pot with a diameter of 10 (?1 g and a depth of 10 mm) was filled with upland soil, sown with barnyard grass, oats, morning glory, and Japanese strawberry, and covered with soil. Formulation Example 2 The test compound was made into an emulsion in the same manner, diluted with a predetermined amount of water equivalent to 10 liters per are, and applied to the soil surface using a small sprayer.After treatment, the emulsion was grown in a greenhouse for 19 days, and its herbicidal efficacy was investigated. The results are shown in Table 5. Table 5 Test Example 8 Upland Stem and Leaves Treatment Test Area 88 x 28 J, depth 1) The seeds were sown and grown for 18 days.Then, the test compound was made into an emulsion according to Formulation Example 21, a prescribed amount of 5 liters per are containing a spreading agent was diluted with an equivalent amount of water, and the emulsion was applied to the plants using a small sprayer. The treatment was applied uniformly to the entire surface of the stem and leaves from the upper part of the body (b).At this time, the growth conditions of weeds and crops were determined by grass species I (1 to 4 leaf stage, and the plant height was 2).
~12crIt.

The herbicidal efficacy was investigated 20 days after the treatment. The results are shown in Table 6. This test was conducted in a greenhouse during the old age period.

Table 6 Test Example 4 Punishing soil stem and leaf treatment test area 83 x 28 eJ, depth 1) (Open bat I) Filled with upland soil, planted 4 species of morning glory, Japanese fir tree, Japanese crocodile, Ebisugusa, Japanese staghorn, and Japanese grasshopper, and grew for 18 days. Thereafter, the test compound was made into an emulsion as in Formulation Example 2, and a predetermined amount of the emulsion was diluted with water containing a spreading agent equivalent to 5 liters per 1. The entire surface of the plant was treated uniformly.At this time, the growth conditions of weeds and crops were different from that of the grass, but they were at the 1-4 leaf stage and the plant height was 2-12 a.20 days after the treatment, the herbicidal efficacy was investigated. The results are shown in Table 7. This test was conducted in a greenhouse throughout the entire period.

No. 7 (Effects of the Invention) The compound of the present invention has excellent herbicidal efficacy against various weeds that are problematic in soil treatment and foliage treatment in fields,
Since it exhibits selectivity between crops and weeds, it can be used for various purposes as an active ingredient in herbicides.

Claims (3)

[Claims] (1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, R^1 and R^2 are the same or different and represent a hydrogen atom or a lower alkyl group, or ▲ Numerical formula, chemical formula, table, etc. ▼ represents a formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼. R^3 represents a lower alkoxy group, a lower alkyl group, a phenyl group or a halophenyl group, and Z represents CH or a nitrogen atom. ] A fused heterocyclic compound represented by (2) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, R^1 and R^2 are the same or different and represent a hydrogen atom or a lower alkyl group, or ▲ Numerical formula, chemical formula, table, etc. ▼ represents a formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼. R^4 represents a lower alkyl group, and Z represents CH or a nitrogen atom. ] An imidazolinone compound represented by the general formula XCH_2COR^3 [wherein R^3 is a lower alkoxy group, a lower alkyl group,
It represents a phenyl group or a halophenyl group, and X represents a chlorine atom or a bromine atom. ] A general formula characterized by reacting a compound represented by the following in the presence of a base ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R^1, R^2, R^3 and Z are as above. expresses the same meaning as ] A method for producing a fused heterocyclic compound represented by (3) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, R^1 and R^2 are the same or different and represent a hydrogen atom or a lower alkyl group, or ▲ Numerical formula, chemical formula, table, etc. ▼ represents a formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼. A herbicide characterized in that R^3 represents a lower alkoxy group, a lower alkyl group, a phenyl group, or a halophenyl group, and Z contains a fused heterocyclic compound represented by CH as an active ingredient.