JPH0436284A - Diphenylfuropyrimidine derivative, its production and herbicide containing the same derivative as active ingredient - Google Patents

Abstract

NEW MATERIAL:A diphenylfuropyrimidine derivative expressed by formula I (R<1> is halogen, lower alkyl, lower haloalkyl, lower alkoxy, lower alkylthio, lower haloalkoxy or lower haloalkylthio which is situated to ortho or meta position; R<2> is H, halogen or lower haloalkyl; R<3> is lower alkyl). EXAMPLE:5-Methylfuro[3,2-d]-2-phenyl-4-(3-chlorophenyl)pyrimidine. USE:Useful as a herbicide. The compound expressed by formula I has excellent weeding effects on various weeds to be the cause of problems in treating foliage and soil in farm and further in treating heated water in paddy field, and exhibits an excellent selectivity between a main crop such as rice and weeds. PREPARATION:A pyrimidine derivative expressed by formula II (R<4> is H or lower alkyl) is heated to provide the compound expressed by formula I. The above-mentioned reaction is carried out at 100-300 deg.C without using any solvent or, otherwise, in a solvent such as decalin.

Description

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

<Problems to be solved by conventional techniques and inventions> Are more herbicides being used than before, or are they insufficient in herbicidal efficacy or have poor selectivity between crops and weeds? It is difficult to say that this is necessarily satisfactory.

Furthermore, it has not been known so far that compounds having a furopyrimidine skeleton have herbicidal activity.

Means to solve problems〉 The present inventors are indicated by the following successive generations [I].

The inventors have discovered that diphenylfuropyrimidine derivatives are compounds that have excellent herbicidal efficacy and exhibit excellent selectivity between crops and weeds, leading to the present invention.

That is, the present invention relates to the general formula [I] [wherein R1 is a halogen atom at the ortho or meta position, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a lower alkylthio group, a lower haloalkoxy group, or a lower haloalkylthio group represents. R2 is a hydrogen atom,
represents a halogen atom, lower)\roalkyl group, and R3 represents a lower alkyl group. ] The present invention provides a diphenylfuropyrimidine derivative (hereinafter referred to as the invention compound) represented by the following, a method for producing the same, and a herbicide containing the same as an active ingredient.

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

General formula [11] [In the formula, R1 and R1 have the same meanings as above, and R
4 represents a hydrogen atom or a lower alkyl group. ] It can be produced by heating the pyrimidine derivative shown below.

This reaction is usually carried out without a solvent or in a solvent, with a reaction temperature of 100 to 300°C and a reaction time of 0.5 to 10 hours.

When using a solvent, examples of the solvent used include aliphatic hydrocarbons such as decalin, halogenated hydrocarbons such as dichlorohensen, tertiary amines such as N, N=nidimethylaniline, and sulfur compounds such as sulfolane. etc. or a mixture thereof.

After completion of the reaction, the reaction solution can be subjected to conventional post-treatments such as organic solvent extraction and concentration, and if necessary, purified by operations such as chromatography and recrystallization to obtain the desired compound of the present invention. .

Next, Table 1 shows some of the compounds of the present invention produced by these production methods.

The flubirimicin derivatives shown in Table 1 have the general formula [
The pyrimidine derivative represented by ID has the same meaning as above. ] A pyrimidine derivative represented by the general formula [■] R''-C-
C-CH20H [In the formula, R4 represents the same meaning as above. It can be produced by reacting with an alcohol derivative shown in ].

The reaction is usually carried out in a solvent, and the reaction temperature range is 20°C.
~100°C, the standard reaction time range is 0.5 to 5 hours, and the amount of reagent used for the reaction is the general [nI] per equivalent of the compound represented by the general formula [■]. The metal alkoxide represented by is usually 1 to 10 equivalents.

Solvents used in the reaction include aliphatic hydrocarbons such as hexane, heptane, ligroin, and petroleum ether, aromatic hydrocarbons such as benzene, toluene, and xylene, halogenated hydrocarbons such as chlorobenzene and dichlorobenzene, and diethyl. Ethers such as diisopropyl ether, dioxane, tetrahydrofuran, diethylene glycol dimethyl ether, methanol, ethanol,
Examples include alcohols such as isopropanol, esters such as ethyl acetate butyl acetate, acid amides such as N,N-dimethylformamide and acetamide, sulfur compounds such as dimethyl sulfoxide, and mixtures thereof.

The compound represented by the general formula [■] is EP 0354766
It can be produced by the method described in A2.

The compounds of the present invention can be used to treat various weeds that are problematic in foliar and soil treatments in upland areas, such as purslane, chickweed, whiteweed, white radish, Japanese radish, Japanese radish, and other weeds.
Shepherd's purse, American hornwort, Ebisugusa, Ichibi,
American Golden Deer Field Pansy, Yaegura,
Broad-leafed weeds such as American morning cacao, Maruba morning cacao, St. convolvulus, Helicoptera trichomes, Hotokenoza, White-bellied morning glory, Physalis japonica, Physalis occidentalis, Japanese fir tree, sunflower, dog mottle, corn maricold, barnyard grass, Japanese millet, Japanese foxtail grass, black-leaved weed,
Sparrow sparrow, Japanese sparrow, gnome, oat,
The compound of the present invention has a herbicidal effect against grass weeds such as oats, and does not cause any problematic phytotoxicity to major crops such as rice.

In addition, the compound of the present invention has a herbicidal effect on various weeds that are problematic in the flooding treatment of rice fields, for example, grass weeds such as Japanese millet, broad-leaved weeds such as acetifolia, psyllium, and chickweed. It does not show any harmful effects on phytotoxicity.

Furthermore, the compound of the present invention can be used in paddy fields, upland fields, orchard pastures,
It can be used as a herbicide for lawns, forests, non-agricultural lands, etc., and can be expected to increase its herbicidal efficacy by mixing it with other herbicides. In addition, insecticides,
It can also be used in combination with acaricides, nematicides, fungicides, plant growth regulators, fertilizers, soil conditioners, etc.

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 suspensions, granules, etc.

These preparations contain the compound of the present invention as an active ingredient in a weight ratio of 1 to 80%, preferably 2 to 70%.

As solid carriers, fine powders or granules such as kaolin clay, asotapulsite clay, hendnant, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, walnut powder, urea, ammonium sulfate, synthetic hydrous silicon oxide, etc. can be used. Examples of liquid carriers include aromatic hydrocarbons such as xylene and methylnaphthalene, alcohols such as isopropanol, ethylene glycol, and cellosolve, ketones such as acetone, cyclohexanone, and isophorone, vegetable oils such as soybean oil and cottonseed oil, and dimethyl sulfonate. Kishi F, N, N-
Examples include dimethylformamide, acetonitrile, water, etc.

Surfactants used for emulsification, dispersion, wetting layers, etc. include alkyl sulfate salts, alkyl sulfonate salts, alkylaryl sulfonate salts, dialkyl sulfosuccinate salts, polyoxyethylene alkylaryl ether phosphate salts, etc. Nonionic surfactants such as anionic surfactants, polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene polyoxypropylene block copolymers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, etc. .

As formulation adjuvants, lignin sulfonate alginate, polyvinyl alcohol, gum arabic, CMC (
carboxymethyl cellulose), PAP (impropyl acid phosphate), etc.

The compound of the present invention is usually formulated and treated with soil, foliage, or flooding before or after the emergence of weeds. Soil treatment includes soil surface treatment, soil mixing treatment, etc., and foliage treatment includes treatment from above the plant body, as well as local treatment that treats only weeds so that they do not attach to crops.

When the compound of the present invention is used as an active ingredient of a herbicide, the amount to be treated will vary depending on weather conditions, formulation form, treatment time, method, location, target weeds, target crops, etc., but usually 1.
10 g to 10,000 g per hectare, preferably 50 to 500 g, and the predetermined amount of emulsions, wetting agents, suspending agents, etc. is usually 1 liter to 1 liter per hectare.
It is diluted with 0 liters of water (if necessary, auxiliary agents such as spreading agents are added) for treatment, and granules and the like are usually treated as they are without any dilution.

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

<Examples> The present invention will be explained in more detail below using production examples, formulation examples, and test examples, but 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 2-phenyl-4-(310lophenyl)-5-propargyloxypyrimicin Ig and 0.5-sulfolane were mixed and heated at 250°C for 3 hours.

After cooling to room temperature, the formed crystals were filtered and purified by silica gel column chromatography, and 5-methylfuroC3,2-d)-2-phenyl-4-(3-chlorophenyl)pyrimidine (the present compound (1) ) 0.6g was obtained.

Melting point: 120.0°C Next, the compound of the present invention produced by this production method (
The details are shown in Table 2.

Examples of formulations of flubirimicin derivatives shown in Table 2 are shown below. The compounds of the present invention are indicated by compound numbers in Table 2.

Parts are parts by weight.

Preparation, fll 1 50 parts of the compound (3) of the present invention, 3 parts of calcium lignosulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of synthetic hydrated silicic acid are thoroughly ground and mixed to obtain a wettable powder.

Formulation Example 2 10 parts of the compounds (2) and (3) of the present invention, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate, and 70 parts of xylene are thoroughly mixed to obtain an emulsion.

Formulation Example 3 2 parts of the compounds (1) and (4) of the present invention, 1 part of synthetic hydrous silicon oxide
1 part, 2 parts of calcium lignin sulfonate, 30 parts of bentonite, and 65 parts of kaolin clay were thoroughly ground and mixed.
After adding water and kneading thoroughly, the mixture is granulated and dried to obtain granules.

Formulation Example 4 25 parts of the present compounds (2) and (3), 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC, 69 parts of water
A suspension is obtained by mixing the two parts and wet milling until the particle size is less than 5 microns.

Next, test examples demonstrate that the compounds of the present invention are useful as active ingredients of herbicides. The compounds of the present invention are indicated by the compound numbers in Table 2, and the compounds used for comparison are indicated by the compound symbols in Table 3.

In addition, the herbicidal efficacy was determined by visually observing the degree of budding and growth inhibition of the test plants during the survey, and ``0'' indicates no difference from the case where the compound was not tested. Plants withering or completely inhibited growth are evaluated as "5j" on an 11 scale scale of θ to 10, with a rating of 0.1.
2.3.4.5.6.7.8.9.10.

Test Example 1 Field field stem and leaf treatment test A cylindrical plastic pot with a diameter of 10 cm and a depth of 10 cm was filled with field soil, and radish, Japanese radish, and Japanese morning glory were sown and grown for one day in a greenhouse. Thereafter, the test compound was made into an emulsion according to Formulation Example 2, a predetermined amount of the emulsion was diluted with water containing a spreading agent equivalent to 10 liters per are, and the foliage was treated from above the plant using a small sprayer. After treatment, the herbicidal efficacy was investigated on growth in a greenhouse for 20 days. The results are shown in Table 4.

4. After culturing, two-leaf stage rice was transplanted and grown in a greenhouse. 6
A day later (at the beginning of the emergence of each weed), the test compound was made into an emulsion according to Formulation Example 2, a predetermined amount of the emulsion was diluted with 5 milliliters of water, and the emulsion was applied to the water surface. Grow in a greenhouse for 20 days after treatment,
The herbicidal efficacy was investigated.

The results are shown in Table 5.

Table 5 Test Example 2 Paddy field flooding treatment test A cylindrical plastic pot with a diameter of 8 cm and a depth of 12 on was filled with paddy soil, and seeds of Japanese millet were mixed in at a depth of 1 to 2 cm. Flooded paddy fields (Effects of the invention) The compound of the present invention has excellent herbicidal efficacy against various weeds that are problematic in foliage treatment and soil treatment of upland fields, as well as in the treatment of flooded paddy fields. In addition, it exhibits excellent selectivity between major crops such as rice and weeds, so it can be used as an active ingredient in herbicides for various purposes.

Claims (3)

[Claims] (1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, R^1 is a halogen atom at the ortho or meta position, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a lower alkylthio group, a lower halo Represents an alkoxy group or a lower haloalkylthio group. R^2 represents a hydrogen atom, a halogen atom, or a lower haloalkyl group;
3 represents a lower alkyl group. ] A diphenylfuropyrimidine derivative represented by (2) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, R^1 is a halogen atom at the ortho or meta position, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a lower alkylthio group, a lower halo Represents an alkoxy group or a lower haloalkylthio group. R^2 represents a hydrogen atom, a halogen atom, or a lower haloalkyl group. R
^4 represents a hydrogen atom or a lower alkyl group. ] The method for producing a diphenylfuropyrimidine derivative according to claim (1), characterized in that the pyrimidine derivative represented by these is heated. (3) A herbicide containing the diphenylfuropyrimidine derivative according to claim (1) as an active ingredient.