JPH04342573A - New (thio)glycolic acid derivative and its salt and herbicide containing the same as active ingredient - Google Patents

Abstract

PURPOSE:To obtain a new compound, having high herbicidal activity and useful as a herbicide excellent in safety for crops. CONSTITUTION:A compound, e.g. methyl 2-(2-methylthio-6-methoxypyrimidinyl-4- oxy)-3-methylbutanoate expressed by formula I (R is lower alkyl, lower cycloalkyl, etc.; X is lower alkyl, halogen-substituted lower alkyl, lower alkoxy, etc.; Y is lower alkoxy, lower alkenoxy, lower alkynoxy, etc.; W is lower alkyl; Z is O or S). Furthermore, the compound expressed by formula I is obtained by reacting a mixture of an alkyl iodide expressed by formula II with a substituted thioglycolic acid expressed by formula III in the presence of a base such as sodium carbonate in an organic solvent such as methanol at a temperature within the range of cooling with ice to the boiling point of the solvent for 1-48hr. The content of the compound expressed by formula I in a herbicide is preferably 1-80wt.% depending on the form of the formulation.

Description

[Detailed description of the invention]

0001

[Industrial Application Field] The present invention relates to a novel (
This invention relates to thio)glycolic acid derivatives and herbicides containing them as active ingredients.

0002

[Prior Art] In order to protect agricultural crops from weed damage and increase yields, various systems of compounds have been researched, and many types of herbicides have been used in practical situations, making great contributions to increasing agricultural productivity. This is known. However, the activity of these compounds against weeds and their safety for crops are
It's not always satisfying.

[0003] Compounds having a similar structure to the compounds of the present invention include Fidiolotiesky Aktivnye Besiestova (Фкзиолочаский Αктивн
18 volumes, 75 pages (1986)
, the following general formula (A)

0004

[Chemical formula 3]

2-phenyl-2-(pyrimidinyl-2-thio)acetic acid and its related compounds have been described. Here, in the above general formula (A), R1 and R
2 represents a group selected from a hydrogen atom, a methyl group, a trifluoromethyl group, a diethylaminoxy group, a phenyl group, and a methoxy group, R3 represents a group selected from hydrogen or a phenyl group, and R4 represents a hydroxy group and its sodium salt represents.

[0006]

[Problems to be Solved by the Invention] However, there is no description of the herbicidal effect of the compounds described in the above literature;
Regarding its effects, only insecticidal activity and nematocidal activity are described.

As a result of intensive research into (thio)glycolic acid-based compounds to develop compounds with high herbicidal effects and excellent safety for crops, the present inventors found that the pyrimidine ring with a specific substituent is The present invention was completed by discovering that a novel (thio)glycolic acid derivative bonded at the 2-position exhibits excellent herbicidal effects against not only annual but also perennial weeds.

[0008]

[Means for Solving the Problems] The compound of the present invention has the following general formula (I).

[0009]

[C4]

(In the formula, R represents a lower alkyl group, a lower cycloalkyl group, a lower alkyl group substituted with a halogen atom, a lower alkenyl group, or a lower alkynyl group. Lower alkyl group, optionally substituted aryl group, lower alkoxy group, lower alkoxy group substituted with a halogen atom, lower alkenoxy group, lower alkynoxy group, optionally substituted aryloxy group, mono- or double substitution Indicates a di-lower alkyl-substituted amino group, a lower alkylthio group, or a lower alkylsulfonyl group, which groups may be bonded together to form a ring structure.Y is a lower alkoxy group, a lower alkenoxy group, a lower alkynoxy group, even if substituted W indicates a good aryloxy group, hydroxy group, hydroxyamino group, lower alkoxyamino group, lower alkenoxyamino group, lower alkynoxyamino group, optionally substituted aryloxyamino group or alkylideneaminoxy group. represents a lower alkyl group; Z represents a sulfur atom or an oxygen atom) and its salt.

In the general formula (I), R represents a lower alkyl group, a lower cycloalkyl group, a lower alkyl group substituted with a halogen atom, a lower alkenyl group, or a lower alkynyl group, and among these, isopropyl group , sec-butyl group, tertiary-butyl group, or cyclopentyl group are preferred.

[0012] X is a lower alkyl group, a lower alkyl group substituted with a halogen atom, an optionally substituted aryl group, a lower alkoxy group, a lower alkoxy group substituted with a halogen atom, a lower alkenoxy group, a lower alkynoxy group. group, an optionally substituted aryloxy group, a di-lower alkyl-substituted amino group, a lower alkylthio group, or a lower alkylsulfonyl group that may have a ring structure formed by bonding mono or two substituents. Among these, methoxy group or methylthio group is preferred.

Further, Y is a lower alkoxy group, a lower alkenoxy group, a lower alkynoxy group, an optionally substituted aryloxy group, a hydroxy group, a hydroxyamino group,
lower alkoxyamino group, lower alkenoxyamino group,
Indicates a lower alkynoxyamino group, an optionally substituted aryloxyamino group, or an alkylideneaminoxy group, among which methoxy, ethoxy, isopropoxy, hydroxy, benzyloxy, allyloxy groups , or propargyloxy group are preferred.

In the above general formula (I), specific examples of the respective groups and atoms in the definitions of X, Y, W and R are shown below.

Lower alkyl groups; for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, tert-pentyl, hexyl, heptyl, octyl or isomers thereof, etc. Cycloalkyl group; for example, cyclobutyl, cyclopentyl or cyclohexyl, lower alkyl group substituted with a halogen atom; for example, chloromethyl, dichloromethyl, trichloromethyl, chloroethyl, dichloroethyl, bromomethyl, dibromomethyl, tribromomethyl, bromoethyl, fluoro Lower alkenyl groups such as methyl, difluoromethyl, trifluoromethyl or trifluoroethyl; Lower alkynyl groups such as vinyl, allyl or propenyl; Lower alkoxy groups such as ethynyl or propargyl; Lower alkoxy groups such as methoxy, ethoxy, propoxy, Lower alkoxy groups substituted with halogen atoms, such as butoxy, isopropoxy, isobutoxy, sec-butoxy or tertiary-butoxy; for example,
Optionally substituted aryl groups such as monofluoromethoxy, difluoromethoxy or trifluoromethoxy; for example, phenyl,
Di-lower alkyl-substituted amino groups which may have mono or two substituents bonded to form a ring structure, such as naphthyl, fluorenyl, indanyl, 3,5-dinitrophenyl, para-nitrophenyl or 3,4-dinitrophenyl; e.g. , methylamino, ethylamino, propylamino, isopropylamino, dimethylamino, diethylamino, 1-pyrrolidinyl or 1-piperidino, etc., lower alkenoxy groups such as vinyloxy, allyloxy or isopropenyloxy, lower alkynoxy groups such as ethynyloxy or an optionally substituted aryloxy group such as propargyloxy; for example, phenoxy, tolyloxy, mesityloxy, fluorophenoxy or chlorophenoxy; lower alkoxyamino group; for example, methoxyamino, ethoxyamino, propoxyamino or Lower alkenoxyamino groups such as isopropoxyamino; for example, lower alkynoxyamino groups such as vinyloxyamino, allyloxyamino or isopropenyloxyamino; even if substituted, such as ethynyloxyamino or propargyloxyamino Good aryloxyamino groups; for example, phenoxyamino, tolyloxyamino, mesityloxyamino,
Salts when Y is a hydroxy group, such as fluorophenoxyamino or chlorophenoxyamino; agrochemically acceptable salts such as sodium, potassium, ammonium, isopropylammonium or triethylammonium; lower alkylthio groups; for example, Lower alkylsulfonyl groups such as methylthio, ethylthio, propylthio or isopropylthio; for example, methylsulfonyl or ethylsulfonyl; alkylideneaminoxy groups; such as ethylideneaminoxy or isopropylideneaminoxy;

Specific examples of the compounds of the present invention represented by the general formula (I) are shown in Table 1 below. In Table 1, “Me
" is a methyl group, "Et" is an ethyl group, "s-butyl
" means a sec-butyl group, "t-butyl" means a tertiary-butyl group, and "c-pentyl" means a cyclopentyl group.

[0017]

[Table 1]

Compound (I) of the present invention can be produced, for example, by the methods shown below (method A, method B, method C, or method D), but the method is not limited to these methods. A law

[0019]

[C5]

(wherein R, Producing the mixture of substituted thioglycolic acids of (3) in the absence of a solvent or in the presence of an appropriate solvent, by adding an appropriate base and reacting for 1 to 48 hours under ice cooling or at a temperature within the boiling point of the solvent. Can be done.

Solvents used in this reaction include, for example, alcoholic solvents such as methanol and ethanol; hydrocarbon solvents such as benzene, toluene and xylene; halogenated hydrocarbon solvents such as dichloromethane and chloroform; diethyl ether. , diisopropyl ether, tetrahydrofuran, 1,4-dioxane, and other ether solvents; dimethylformamide, dimethylsulfoxide, dimethylacetamide, and other aprotic polar solvents;
Examples include acetonitrile and water. Also,
Examples of bases include carbonates such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate, and potassium hydrogen carbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; metal alcoholates such as sodium methylate and sodium ethylate; hydrogenation. Examples include alkali metal hydrides such as sodium and potassium hydride.

0022 Method B

[0023]

[C6]

(In the formula, R, The compound represented by -b) is prepared by adding a mixture of the carboxylic acid derivative of formula (4) and the substituted pyrimidine of formula (5) without a solvent or in the presence of an appropriate solvent.
It can be produced by adding an appropriate base and reacting for 1 to 48 hours under ice cooling or at a temperature within the boiling point of the solvent.

Solvents used in this reaction include, for example, alcoholic solvents such as methanol and ethanol; hydrocarbon solvents such as benzene, toluene and xylene; halogenated hydrocarbon solvents such as dichloromethane and chloroform; and diethyl. Ether solvents such as ether, diisopropyl ether, tetrahydrofuran, and 1,4-dioxane; Ketone solvents such as acetone and methyl ethyl ketone; Ester solvents such as methyl acetate and ethyl acetate;
Examples include aprotic polar solvents such as dimethylformamide, dimethylsulfoxide, and dimethylacetamide; acetonitrile, water, and the like.

As bases, carbonates such as sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; sodium methylate, sodium ethylate, etc. Metal alcoholates; alkali metal hydrides such as sodium hydride and potassium hydride can be mentioned.

Method C This method C is a method for producing a compound in the above general formula (I) in which Y corresponds to a hydroxy group or a salt thereof.

[0028]

[C7]

(wherein R, In the above reaction formula, the compound represented by formula (6) is prepared by reacting the compound represented by formula (I-c) with a suitable base in the presence of a suitable solvent at room temperature or It can be produced by reacting for 1 to 24 hours at a temperature within the boiling point of the solvent. In addition, by treating the compound represented by formula (6) with an acid, the formula (
The compound shown in 7) can be produced.

Solvents used in this reaction include, for example, alcoholic solvents such as methanol, ethanol, and isopropyl alcohol; hydrocarbon solvents such as benzene, toluene, and xylene; and halogenated hydrocarbon solvents such as dichloromethane and chloroform. ; diethyl ether, diisopropyl ether, tetrahydrofuran, 1,
Ether solvents such as 4-dioxane; ketone solvents such as acetone and methyl ethyl ketone; ester solvents such as methyl acetate and ethyl acetate; aprotic polar solvents such as dimethylformamide, dimethyl sulfoxide, and dimethyl acetamide; acetonitrile, water, etc. can be mentioned.

Bases include carbonates such as sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; metals such as sodium methylate and sodium ethylate. Alcoholate: Alkali metal hydrides such as sodium hydride and potassium hydride can be mentioned. Method D This method D is a method for producing a compound in which Y corresponds to a group other than hydroxyl group from a compound in which Y corresponds to a hydroxy group in the general formula (I).

[0032]

[Chemical formula 8]

(In the formula, R, X, W, Y' and Z have the same meanings as above. Also, T represents a hydroxy group or a halogen atom.) In the above reaction formula, in the formula (I-c) The represented compound is prepared by combining the carboxylic acid of formula (7) with an appropriate alkyl halide or alcohol using an appropriate condensing agent, in the absence of a solvent or in the presence of an appropriate solvent, under ice cooling or at a temperature within the boiling point of the solvent. , can be produced by reacting for 1 to 24 hours.

Solvents used in the reaction include alcohol solvents such as methanol, ethanol and isopropyl alcohol; hydrocarbon solvents such as benzene, toluene and xylene; halogenated hydrocarbon solvents such as dichloromethane and chloroform; diethyl ether, Ether solvents such as diisopropyl ether, tetrahydrofuran, and 1,4-dioxane; Ketone solvents such as acetone and methyl ethyl ketone; Ester solvents such as methyl acetate and ethyl acetate; Aprotic polar solvents such as dimethyl formamide, dimethyl sulfoxide, and dimethyl acetamide Solvent: Acetonitrile, water, etc. can be mentioned.

As condensing agents, carbonates such as sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; sodium methylate, sodium ethylate, etc. Metal alcoholates; alkali metal hydrides such as sodium hydride and potassium hydride; organic bases such as diazabicycloundecene; and dehydration condensation agents such as dicyclohexylcarbodiimide.

Next, the present invention will be explained in more detail with reference to Examples.

[0037]

[Example 1] Methyl 2-(2-methylthio-6-methoxypyrimidinyl-4-oxy)-3-methylbutanoate (
Synthesis of compound number 1); 2-hydroxy-3-methyl-
Methyl butanoate 0.53g (4mmol) and 4-chloro-2-methylthio-6-methoxypyrimidine 0.76g
(4 mmol) was dissolved in 20 ml of N,N-dimethylformamide and added with 0.69 g (5 mmol) of potassium carbonate.
1) was added and stirred at 40°C for 5 hours. The reaction solution was cooled and 50 ml of water was added, followed by extraction three times with 30 ml of dichloromethane. After washing three times with 100 ml of water, the dichloromethane layer was dried over anhydrous magnesium sulfate and evaporated under reduced pressure to obtain a crude product. This was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate = 9/1) to obtain the desired methyl 2-(2-methylthio-6-methoxypyrimidinyl-4-oxy)-3-methylbutanoate (
Compound No. 1) 0.97 g (yield 85%) was obtained.

1H-NMR (δ, CDCl3) 5.79
(s, 1H), 5.01 (d, 1H), 3.88 (s,
3H), 3.67 (s, 3H), 2.43 (s, 3H)
, 2.30 (sep, 1H), 1.04 (d, 6H)

[
0039

[Example 2] 2-(2,6-dimethoxypyrimidinyl-
Synthesis of 4-oxy)-3-methylbutanoic acid (compound number 5); 1.08 g (4 mm
ol) was added to a mixed solution of 5 ml of methanol and 5 ml of water, 0.3 g of potassium hydroxide was added, and the mixture was stirred at 40° C. for 5 hours. After cooling the reaction solution and adding 50 ml of water, it was made acidic with dilute hydrochloric acid and extracted three times with 30 ml of dichloromethane. The dichloromethane layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off to obtain the desired 2-(2,6-dimethoxypyrimidinyl-4-oxy)-3-methylbutanoic acid (Compound No. 5) 0.89 g (yield 87%). ) was obtained.

1H-NMR (δ, CDCl3) 11.0
0 (bs, 1H), 5.77 (s, 1H), 5.03 (
d, 1H), 3.88 (s, 3H), 3.85 (s, 3
H), 3.26 (sep, 1H), 1.09 (d, 6H
)

[0041]

[Example 3] Allyl 2-(2-methoxy-6-methylthiopyrimidinyl-4-oxy)-3-methylbutanoate (
Synthesis of compound number 7): Dissolve 0.82 g (3 mmol) of 2-(2-methylthio-6-methoxypyrimidinyl-4-oxy)-3-methylbutanoic acid in 10 ml of N,N-dimethylformamide, and add 0.0 ml of potassium carbonate to this. .41
g (3 mmol) and allyl bromide 0.6 g (5 mmol)
1) was added and stirred at 50°C for 5 hours. The reaction solution was cooled and 50 ml of water was added, followed by extraction three times with 30 ml of ethyl acetate. After washing three times with 100 ml of water, the ethyl acetate layer was dried over anhydrous magnesium sulfate and evaporated under reduced pressure to obtain a crude product. This was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate = 9/1) to obtain the desired 2-(2-methoxy-6-methylthiopyrimidinyl-
0.66 g (yield 70%) of allyl 4-oxy)-3-methylbutanoate (compound number 7) was obtained.

1H-NMR (δ, CDCl3) 6.23
(s, 1H), 5.0-6.1 (m, 3H), 4.5-
4.7 (m, 2H), 4.59 (d, 2H), 3.90
(s, 3H), 2.50 (s, 3H), 2.28 (se
p, 1H), 1.07 (d, 6H) Compounds listed in Table 1 were synthesized by the same method. The NMR data and/or melting points of these compounds are shown in Table 2 below.

[0043]

[Table 2]

The herbicide of the present invention contains the novel (thio)glycolic acid derivative of the above general formula (I) as an active ingredient.

When the compound of the present invention is used as a herbicide, it is mixed with a carrier, diluent, additive, auxiliary agent, etc. by a method known per se, and prepared in the form of a formulation commonly used as an agrochemical, such as a powder, etc. It is used by preparing granules, wettable powders, emulsions, aqueous solutions, flowable preparations, etc. It can also be mixed or used in combination with other agricultural chemicals, such as fungicides, insecticides, acaricides, other herbicides, plant growth regulators, fertilizers, soil conditioners, and the like. In particular, when used in combination with other herbicides, it is possible to not only reduce the amount of chemicals used and save labor, but also to expand the herbicidal spectrum due to the synergistic action of both herbicides, and to achieve even higher effects due to the synergistic action. .

[0046] As the carrier or diluent used in the formulation, solid or liquid carriers commonly used in agriculture are used. Solid carriers include clays such as kaolinite group, montmorillonite group, or apattalgite group, talc, mica, waxite, pumice, vermiculite, gypsum, calcium carbonate, dolomite,
Inorganic substances such as diatomaceous earth, magnesium lime, apatite, zeolite, anhydrous silicic acid, and synthetic calcium silicate; soybean flour, tobacco flour, walnut flour, wheat flour, wood flour, starch,
Vegetable organic substances such as crystalline cellulose; Synthetic or natural polymer compounds such as coumaron resin, petroleum resin, alkyd resin, polyvinyl chloride, polyalkylene glycol, ketone resin, ester gum, cobal gum, and damman gum; Other carnauba wax and beeswax Examples include waxes such as urea and the like.

Suitable liquid carriers include, for example, paraffinic or naphthenic hydrocarbons such as kerosene, mineral oil, spindle oil, white oil; aromatic hydrocarbons such as toluene, xylene, ethylbenzene, cumene, methylnaphthalene; dioxane, Ethers such as tetrahydrofuran; ketones such as acetone, methyl ethyl ketone, diisobutyl ketone, cyclohexanone, acetophenone, isophorone; esters such as ethyl acetate, amyl acetate, ethylene glycol acetate, diethylene glycol acetate, dibutyl maleate, diethyl succinate; methanol, Alcohols such as n-hexanol, ethylene glycol, diethylene glycol, cyclohexanol, benzyl alcohol; Ether alcohols such as ethylene glycol ethyl ether, ethylene glycol phenyl ether, diethylene glycol ethyl ether, diethylene glycol butyl ether; polarity such as dimethylformamide, dimethyl sulfoxide, etc. Examples include a solvent or water.

In addition, surfactants and other auxiliary agents may be used for the purpose of emulsifying, dispersing, wetting, spreading, binding, adjusting disintegrability, stabilizing the active ingredient, improving fluidity, preventing rust, etc. of the compound of the present invention. You can also do that.

Examples of surfactants that can be used include nonionic, anionic, cationic, and zwitterionic compounds, but usually nonionic and (
or) anionic compounds are used. Suitable nonionic surfactants include, for example, compounds obtained by polymerizing and adding ethylene oxide to higher alcohols such as lauryl alcohol, stearyl alcohol, and oleyl alcohol, and compounds obtained by polymerizing and adding ethylene oxide to alkylphenols such as isooctylphenol and nonylphenol. compounds in which ethylene oxide is polymerized and added to alkylnaphthols such as butylnaphthol and octylnaphthol; compounds in which ethylene oxide is polymerized and added to higher fatty acids such as palmitic acid, stearic acid, and oleic acid;
Examples include higher fatty acid esters of polyhydric alcohols such as sorbitan, compounds obtained by polymerizing and adding ethylene oxide thereto, and compounds obtained by block polymerizing and adding ethylene oxide and propylene oxide.

Suitable anionic surfactants include, for example, sodium lauryl sulfate, alkyl sulfate salts such as oleyl alcohol sulfate amine salt, alkyl sulfate salts such as sodium sulfosuccinate dioctyl ester, and sodium 2-ethylhexene sulfonate. Sulfonate salts; aryl sulfonate salts such as sodium isopropylnaphthalenesulfonate, sodium methylenebisnaphthalenesulfonate, sodium ligninsulfonate, and sodium dodecylbenzenesulfonate;

Furthermore, the herbicide of the present invention may contain polymers such as casein, gelatin, albumin, glue, sodium alginate, carboxymethyl cellulose, methyl cellulose, hydroxyethyl cellulose, polyvinyl alcohol, etc., in order to improve the properties of the preparation and increase the herbicidal effect. Compounds and other adjuvants can also be used in combination.

The above-mentioned carriers and various auxiliary agents are used individually or in combination as appropriate depending on the purpose, taking into account the dosage form of the preparation, the application situation, etc.

The content of the compound (active ingredient) of the present invention in the various formulations thus obtained varies depending on the formulation, but is usually 0.1 to 99% by weight, particularly 1% by weight. -80% by weight is most preferred.

[0054] In the case of a powder, the active ingredient compound is usually contained in an amount of 1 to 25% by weight, and the remainder is a solid carrier.

In the case of a wettable powder, for example, the active ingredient compound is usually contained in an amount of 25 to 90% by weight, and the remainder is a solid carrier, a dispersion wetting agent, and if necessary, a protective colloid agent, an antifoaming agent, etc. are added. It will be done.

In the case of granules, for example, the active ingredient compound is usually contained in an amount of 1 to 35% by weight, with the remainder being mostly solid carriers, surfactants, and the like. The active ingredient compound is uniformly mixed with the solid carrier, or is uniformly fixed or adsorbed on the surface of the solid carrier, and the particle size is about 0.2 to about 1.5 mm.

In the case of an emulsion, for example, it usually contains 5 to 30% by weight of the active ingredient compound, this includes about 5 to about 20% by weight of an emulsifier, and the remainder is a liquid carrier.
Rust inhibitors are added if necessary.

In the case of a flowable agent, for example, it usually contains 5 to 50% of the active ingredient compound, and 3 to 1% of the active ingredient compound.
It contains 0% by weight of a dispersion wetting agent and the remainder is water, with protective colloids, preservatives, antifoaming agents, etc. added as necessary.

The novel (thio)glycolic acid derivatives and salts thereof of the present invention can be used as compounds of general formula (I) or in any preparation form as described above.

The herbicide of the present invention can be applied to exterminate or control various weeds growing in rice fields and fields from before their emergence to the growing season. The application amount is 0.01 to 5k per ha as the amount of the compound represented by general formula (I) (amount of active ingredient)
The amount can be changed as appropriate depending on the type of target weed, growth stage, application site, application time, weather, etc.

Next, several embodiments of formulations using the compounds of the present invention will be shown. "Parts" in the following formulation examples are based on weight.

Formulation Example 1 (Granules) Compound No. 1
Part 5 bentonite
50 parts talc

40 parts Sodium dodecylbenzenesulfonate 2 parts Sodium ligninsulfonate
After thoroughly mixing 2 parts and 1 part or more of polyoxyethylene styryl phenyl ether, an appropriate amount of water was added and kneaded, followed by granulation using a granulator to obtain 100 parts of granules.

Formulation example 2 (hydrating powder) Compound No. 6
Part 20 Diatomaceous earth
60 parts white carbon
15 parts Sodium ligninsulfonate
Part 3
Sodium dodecylbenzenesulfonate
Two or more parts were mixed and uniformly mixed and pulverized using a kneader to obtain 100 parts of a wettable powder.

Formulation Example 3 (Emulsion) Compound No. 7
30 parts xylene
55 parts cyclohexanone
10 parts calcium dodecylbenzenesulfonate 3 parts polyoxyethylene styrylphenyl ether 2 parts or more were uniformly mixed and dissolved to obtain 100 parts of an emulsion.

Drugs using the compounds of the present invention were prepared according to the above-mentioned formulation examples.

[0066]

Effects of the Invention: The compound represented by the above general formula (I) of the present invention
Thio)glycolic acid derivatives and their salts are novel compounds that have not been described in any literature. The compound represented by the above general formula (I) of the present invention has a structure in which the pyrimidine ring portion with specific substituents bonded to the 2- and 6-positions is bonded to the 2-position of the fatty acid. It is thought that this (thio)glycolic acid derivative exhibits excellent herbicidal performance due to its structural characteristics.

The compounds and herbicides of the present invention can control various weeds growing in agricultural land from pre-emergence to growth stage. For example, paddy field weeds such as field weeds, scallops, water holly, water holly, azalea, water chickweed, staghorn grass, pine snail, and snail grass, as well as staghorn grass, foxtail grass, hawkweed, sycamore, sparrow gnome, chickweed, polygonum, coccinaceae, crocodile, whiteweed, and American golden deer. It can control various weeds in upland areas such as Japanese fir, ragweed, shepherd's purse, ashweed, meadowweed, cornweed, and buckwheat. Furthermore, it can be used not only in rice fields and fields, but also in orchards, mulberry gardens, lawns, and non-agricultural lands.

Moreover, the compound of the present invention has selectivity for cultivated crops, and is particularly excellent in selectivity for dicotyledonous crops such as soybean, cotton, and sunflower, and does not cause any phytotoxicity that is a practical problem. Next, the effect of the herbicide of the present invention will be explained by giving test examples.

Test Example 1 (Paddy field weed pre-germination treatment) A square pot (14 x 14 x 9 cm) was filled with paddy soil, and an appropriate amount of water and chemical fertilizer were added and kneaded to form a paddy field. to this,
Two rice seedlings were grown in advance to have two leaves, and two plants were transplanted into each pot. Further, seeds and tubers of various weeds shown in Table 3 were sown in fixed amounts, and each compound shown in Table 3 was prepared into granules according to Formulation Example 1 and treated. 27 days after the chemical treatment, the herbicidal effect on each weed was determined according to the following criteria. The results are shown in Table 3.

Evaluation criteria for herbicidal effect (11 levels) Score
Weed killing rate (%) for untreated area 0
0
1 0
Over -10 or less 2
Over 10 -20 or less 3
Over 20 -3
0 or less 4
Over 30 and below -40 5
Over 40 -50 or less
6 50
Over -60 or less 7
Over 60 - 70 or less 8
Over 70 -8
0 or less 9
Over 80 -90 or less 10
More than 90-100 or less Test Example 2 (Paddy field weed growing season treatment) The same procedure as Test Example 1 was carried out except that the chemical treatment, paddy rice transplantation, and weed sowing were carried out 10 days later. The results of the test are shown in Table 4.

Test Example 3 (Soil treatment before germination in upland field) Fill a square pot (30 x 30 x 12 cm) with upland soil,
After sowing certain amounts of various crops and various weed seeds shown in the table, the soil was covered with 1 cm of soil. The compounds of the present invention shown in Table 5 were prepared into wettable powders according to Formulation Example 2, and the diluted solutions were evenly spread over the soil surface so that the amounts of active ingredients shown in Table 5 were obtained. Twenty-one days after the chemical spraying, the herbicidal effects on various weeds were determined according to the criteria of Test Example 1. The results are shown in Table 5.

Test Example 4 (field soil stem leaf treatment) Square pot (3
0 x 30 x 12 cm) was filled with field soil, and certain amounts of various crops and weed seeds shown in Table 6 were sown, and each seed was grown in a greenhouse until it reached the 1.5-3 leaf stage. The compounds of the present invention shown in Table 6 were prepared into a wettable powder according to Formulation Example 2, and the water diluted solution was evenly sprayed on the leaves and foliage of each plant so that the amount of active ingredient shown in Table 6 was obtained. Twenty-one days after the chemical spraying, the herbicidal effect on various weeds was determined according to the criteria of Test Example 1. The results are shown in Table 6.

[0073]

[Table 3]

[0074]

[Table 4]

[0075]

[Table 5]

[0076]

[Table 6]

Claims (2)

[Claims] Claim 1: General formula (I) [Formula 1] (wherein, R is a lower alkyl group, a lower cycloalkyl group,
Indicates a lower alkyl group, lower alkenyl group, or lower alkynyl group substituted with a halogen atom. X is a lower alkyl group, a lower alkyl group substituted with a halogen atom, an optionally substituted aryl group, a lower alkoxy group, a lower alkoxy group substituted with a halogen atom, a lower alkenoxy group, a lower alkynoxy group, an unsubstituted represents an optional aryloxy group, a di-lower alkyl-substituted amino group, a lower alkylthio group, or a lower alkylsulfonyl group, which may have mono or two substituents bonded to form a ring structure. Y is a lower alkoxy group, a lower alkenoxy group,
Lower alkynoxy group, optionally substituted aryloxy group, hydroxy group, hydroxyamino group, lower alkoxyamino group, lower alkenoxyamino group, lower alkynoxyamino group, optionally substituted aryloxyamino group Or represents an alkylidene aminoxy group. W
represents a lower alkyl group. Z represents a sulfur atom or an oxygen atom. ) (thio)glycolic acid derivatives and their salts. Claim 2: General formula (I) [Formula 2] (wherein, R is a lower alkyl group, a lower cycloalkyl group,
Indicates a lower alkyl group, lower alkenyl group, or lower alkynyl group substituted with a halogen atom. X is a lower alkyl group, a lower alkyl group substituted with a halogen atom, an optionally substituted aryl group, a lower alkoxy group, a lower alkoxy group substituted with a halogen atom, a lower alkenoxy group, a lower alkynoxy group, an unsubstituted represents an optional aryloxy group, a di-lower alkyl-substituted amino group, a lower alkylthio group, or a lower alkylsulfonyl group, which may have mono or two substituents bonded to form a ring structure. Y is a lower alkoxy group, a lower alkenoxy group,
Lower alkynoxy group, optionally substituted aryloxy group, hydroxy group, hydroxyamino group, lower alkoxyamino group, lower alkenoxyamino group, lower alkynoxyamino group, optionally substituted aryloxyamino group Or represents an alkylidene aminoxy group. W
represents a lower alkyl group. Z represents a sulfur atom or an oxygen atom. ) A herbicide containing a (thio)glycolic acid derivative and/or a salt thereof as an active ingredient.