JPH0285262A - Herbicide and novel alkanoic acid derivative useful as active component of same herbicide - Google Patents

Abstract

NEW MATERIAL:The alkanoic acid derivative of formula I (R is hydrocarbon group; R' is H, hydrocarbon group or alkylidenamino; R and R' may together form a lactone ring; A is halogen, alkyl, alkoxy, halogen-substituted alkyl, alkylthio, amino, etc.; B is H, alkyl, alkoxy, etc.; X is O or S; Z is methine or N) or its salt. EXAMPLE:2-(4,6-Dimethoxypyrimidin-2-yl)oxy-3-methyl-3-phenylacetic acid ethyl ester. USE:Useful as a herbicide versatilely applicable to various agricultural crops, effective in killing a wide variety of weeds and harmless to crops. PREPARATION:The compound of formula I can be produced e.g., by reacting a compound of formula II with a compound of formula III (Y1 is halogen, alkylsulfonyl, etc.) in the presence of more than equivalent amount of a base in a solvent.

Description

DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to novel alkanoic acid derivatives and salts thereof, and herbicides containing specific alkanoic acid derivatives or salts thereof as active ingredients.

Conventional technology In recent years, a large number of herbicides have been developed, contributing to labor saving and improving productivity in agricultural work, but these herbicides have specific effects on each crop and weed. Since there are many types of pesticides, it is necessary to select and use the most effective one depending on the area of application and the type of agricultural products. Therefore, the development of new compounds exhibiting herbicidal effects has always been an important issue in this field.

Problems to be Solved by the Invention The present invention provides a novel herbicide that contains as an active ingredient a compound with a chemical structure different from that of conventionally used herbicides and can be used in a variety of ways for the cultivation of various agricultural crops. It was done for the purpose of

Means for Solving the Problems As a result of extensive research to develop compounds that exhibit herbicidal effects, the present inventors discovered that certain alkanoic acid derivatives having a pyrimidine ring or triazine ring, The present inventors have discovered that it is effective against agricultural crops and is also harmless to agricultural crops, and have thus come up with the present invention.

That is, the present invention provides the following method: They may be bonded to each other to form a lactone ring, and A is a haO/7' atom, an alkyl group, an alkoxy group, a halogen-substituted alkyl group, a halogen-substituted alkoxy group, an alkylthio group, an amino group, or a substituted amino group. group, B is a hydrogen atom, an alkyl group, an alkoxy group, a halogen-substituted alkyl group, or a halogen-substituted alkoxy group, X is an oxygen atom or a sulfur atom, and 2 is a methine group or a nitrogen atom); The present invention provides a herbicide containing the salt as an active ingredient.

Until now, as alkanoic acid derivatives having a pyrimidyl ring or a triazyl ring, N-(1-cyanol-1,2-dimethylglobyl)-2-pyrimidinyloxyglopionamide (European Patent No. 262.393), 2-
(4-chloro-6-(4-chlorobenzylamino)-pyrimidinylcothiopropionic acid (West German Patent Publication No. 2)
, No. 314,160), but these have bactericidal and cholesterol-lowering effects, and are not known to have herbicidal effects at all.

In addition, as a synthetic intermediate for sulfonylurea derivatives, -
It is known that R in Fukudai (1) corresponds to a methyl group, R/ to an ethyl group, A to an amine group, B to a methyl group, X to an oxygen molecule, and Z to a nitrogen atom (European Patent Application 30).
．． No. 138), and it is not known that this substance can be used as a herbicide.

Furthermore, in -Fukudai (1), R is a methyl group, an ethyl group, R/ is a methyl group, a butyl group, a ncrohexyl group, and A
Also known are compounds in which B corresponds to a methyl group, X corresponds to a sulfur atom, and 2 corresponds to a methine group (Z.

Chem, 1974, Volume 14, Page 436),
This scale is not known to be used as a herbicide.

Thus, it has not been known at all that the alkanoic acid derivative represented by -Fukudai (1) has herbicidal activity, and this was discovered for the first time by the present inventors.

Furthermore, many of the compounds used as active ingredients in the herbicide of the present invention are new compounds that have not been published in literature. Hydrogen group, R1'
is a hydrogen atom, a hydrocarbon group or a substituted hydrocarbon group,
R, and R, 7 may be bonded to each other to form a lactone ring, and A1 is) a 10-gen atom, an alkyl group, an alkoxy group, a halogen-substituted alkyl group, a hagelon-substituted alkoxy group, an alkylthio group, an amino The group or substituted amino group, B, is a hydrogen atom, an alkyl group, an alkoxy group, a norogen-substituted alkyl group or a halogen-substituted alkoxy group. ), an alkanoic acid derivative represented by the formula (R2 in the formula is a hydrocarbon group having 3 or more carbon atoms, R2' is a hydrogen atom, a hydrocarbon group, a substituted hydrocarbon group, or an alkylidene amino group);
The groups A2 and B2' are each a group selected from an alkyl group, an alkokino group, an amine group, and a substituted amine group, Z
is a methine group or a nitrogen atom. ), an alkanoic acid derivative represented by the formula (R3 in the formula is a hydrocarbon group, 1123' is a hydrogen atom or a hydrocarbon group, and R1 and R1' are bonded to each other to form a lactone ring) and A3 and B are groups selected from an alkyl group and an alkone group, respectively.

Next, the present invention will be explained in more detail.

R in the above-mentioned (1) is a hydrocarbon group or a substituted hydrocarbon group, and examples of this hydrocarbon group include a methyl group, an ethyl group, a lopropyl group, an isobutyl group, an n-
Butyl group, 5ee-butyl group, t-butyl group, isobutyl group, n-pentyl group, impentyl group, 2-ethylpropyl group, ■-methylbutyl group, 1-methyl-1-ethylpropyl group, ■, 1- Straight chain such as dimethylbutyl group, n-heptyl group, n-octyl group, n-non'nyl group, 0-del/l group, n-dodel/l group, 0-tetrazonol group, n-palmityl group or a branched aliphatic saturated hydrocarbon group, a linear or branched aliphatic unsaturated hydrocarbon group such as an ethynyl group, a 70-benyl group, an impropenyl group, a hexenyl group, a propynyl group, a ncropropyl group, a cyclobutyl group, /
Clopentyl group, cyclobutyl group, ncrobentenyl group, ncrohexenyl group, l-methylcyclopentyl group,
Alicyclic hydrocarbon groups such as cyclobentylmethyl group, 2-methylcyclopentenyl group, 3-methylcyclopentyl group, benzyl group, ■-phenylethyl group, l-phenylglobyl group, l-methyl-■- 722 ethyl L l
-Methyl-■-Phenyl70 Pyl group, l-phenylpropenyl group, 4-methylbenzyl group, α-/clopentylbenzyl group, l-methyl-1-naphthylethyl group, dihydronaphthyl group, tetrahydronaphthyl group, intanyl group Examples of substituents for these hydrocarbon groups include alkyl groups, trifluoromethyl groups, halogen atoms, hydroxyl groups, alkoxy groups, alkylthio groups, and alkyl groups. Examples include a sulfinyl group, an alkylsulfonyl group, an acyloxy group, a nitro group, a noano group, a carboxyl group, an oxo group, an epoxy group, and a heterocyclic group such as a furanyl group, a thienyl group, and a dioxolanyl group. Also R
Examples of / include, in addition to a hydrogen atom, the same hydrocarbon group as in the case of R, a substituted hydrocarbon group, and an alkylidene amino group such as an ingropylidene amino group and a benzylidene amino group.

Next, the substituent A on the pyrimidyl ring or triazyl ring includes, for example, a halogen atom such as a chlorine atom, a bromine atom, or a fluorine atom, a methyl group, an ethyl group, a +rpropyl group, an isopropyl group, an n-butyl group, a 5ec -butyl group, [-
Straight-chain or branched alkyl groups such as butyl, n-pentyl, n-hexynyl, alkoxy groups such as methoxy, ethoxy, propoxy, butquine, chloromethyl, chloroethyl, dichloro Ethyl group, bromomethyl group, chloropropyl group, bromopropyl group,
Halogen-substituted alkyl groups such as fluoromethyl group, fluoroethyl group, trifluoromethyl group, chloromethoxy group, bromoethoxy group, dichloroethoxy group, dibromopropoxy group, fluoromethoxy group, difluoroethquine group, difluoroethquine group Halogen-substituted alkoxy groups such as methylthio group, ethylthio group, propylthio group, isopropylthio group, alkylthio group such as inbutylthio group, amino group, methylamino group, ethylamino group, dimethylamino group, diethylamino group, in7
There are substituted amine groups such as 0-bylamino group, imbutylamino group, and butylamino group. Examples of substituent B include hydrogen atoms, as well as alkyl groups and alkokyne groups similar to those for substituent A. , a halogen-substituted alkyl group, or a halogen-substituted alkoxy group.

If R' in the alkanoic acid derivative of (1) is a hydrogen atom, it may be in a free form, or it may be a sodium salt, a potassium salt, a potassium salt, a magnesium salt, an aluminum salt, an iron salt, It may be in the form of a metal salt such as a cobalt salt, or an organic amine salt such as a methylamine addition salt, an ethylamine addition salt, or an isopropylamine addition salt.

Examples of the hydrocarbon group and substituted hydrocarbon group of R in the first term - clothing cost (2) are the same as R in the above - clothing cost (1),
Examples of hydrocarbon groups and substituted hydrocarbon groups for R and I are:
The same items as R' in (1) above can be mentioned. In addition, as examples of the halogen atom, alkyl group, alkoxy group, halogen-substituted alkyl group, halogen-substituted alkoxy group, alkylthio group, and substituted amine group in A, the same as A in -Fukudai (1) is used in Bl. Examples of the alkyl group, alkokene group, halogen-substituted alkyl group, and halogen-substituted alkoxy group include the same groups as B in general formula (1).

Furthermore, as an example of R2 in the above-mentioned clothing cost (3), n-70
Pyl group, isopropyl group, n-butyl group, isobutyl group, 5ee-butyl group, L-butyl group, n-pentyl group,
Impentyl group, 2-ethylpropyl group,! -Methylbutyl group, ■-Methyl-1-ethylglobyl group, l,1 dimethylbutyl group, n-heptyl group, n-octyl group, n
-ynyl L straight chain or branched aliphatic saturated hydrocarbon group such as n-decyl group, n-dodenyl group, n-tetradodenyl group, straight chain such as propenyl group, impropenyl group, hexenyl group, propynyl group Chain or branched aliphatic unsaturated hydrocarbon group, cyclopropyl group, cyclobutyl group, noclopentyl group, nclohexyl group, cyclopentenyl group, cyclohexenyl group, cyclopentylmethyl group, ■
-Alicyclic hydrocarbon groups such as methylcyclopentenyl group, benzyl L l-phenylethyl group, l-phenylpropyl group, l-7enylpropenyl group, α-cyclopentylbenzyl group, l-naphthylethyl group, dihydronaphthyl group Mention may be made of aromatic hydrocarbon radicals such as radicals. In addition to hydrogen atoms, examples of R2' include -fukudai (
The same hydrocarbon groups, substituted hydrocarbon groups, and alkylidene amino groups as R' in 1) can be mentioned, and A2 and B2
Examples include the same alkyl groups, alkokene groups, and substituted amino groups in the case of A and B in -Fukudai (1).

Furthermore, as R1 in -Fukudai (4), the same hydrocarbon group as R in the above-mentioned general formula (1) can be mentioned, and as an example of R8', the same hydrocarbon group as R' can be mentioned, Examples of A and B include the same alkyl groups and alkokino groups as A and B in general formula (1).

Therefore, specific examples of novel compounds among the active ingredients of the herbicide of the present invention include the following.

Compound 418 is in the S(+) form.

The compounds of the present invention can be produced by the methods shown in Reaction Formulas (I) to Reaction Formulas (Vl). However, the method is not limited to these methods.

Reaction formula (I) AI Reaction formula (It) BI (1-a) (wherein, Yl is a halogen atom, an alkylsulfonyl group,
represents a benzylsulfonyl group or a substituted benzylsulfonyl group, Y2 represents a halogen atom or an alkylsulfonyloquine group, and R, R', A, B, X and Z have the same meanings as defined above) - Cost of clothes (1-a)
The compound represented by the formula [A] in reaction formula (I) and the compound represented by the general formula (B), or the compound represented by the general formula [CD] in reaction formula (II), It can be produced by reacting a compound represented by the general formula CD) in an appropriate solvent in the presence of an equivalent or more amount of base at a temperature ranging from room temperature to the boiling point of the solvent for 5 to 24 hours. Here, the base includes metallic sodium,
Alkali metals such as metallic potassium, sodium hydride,
Alkali metal hydrides and alkaline earth metal hydrides such as potassium hydride and calcium hydride, sodium carbonate,
Alkali metal carbonates such as potassium carbonate, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, and organic amines such as triethylamine and pyridine can be used. Examples of solvents include hydrocarbon solvents such as benzene, toluene, and xylene, halogenated hydrocarbon solvents such as methylene chloride, and chloroform, methanol, ethanol, and
- Alcohol solvents such as glopanol, ether solvents such as ethyl ether, tetrahydrofuran, and dioxane, ketone solvents such as acetone and methyl ethyl ketone, ester solvents such as methyl acetate and ethyl acetate, N,N-dimethylformamide, N,N -dimethylacetamide,
Aprotic polar solvents such as dimethyl sulfoxide, acetonitrile, water, etc. can be used.

When R' is hydrogen, a base of 2 equivalents or more is used and the reaction is made acidic to obtain the compound represented by the general formula [1-a).

Reaction formula (III) [:l [B] CF) [l
-b] (wherein RP represents the same or different hydrogen atoms or lower alkyl groups, R7 represents the same or different lower alkyl groups), R, Y, , AlB and 2 has the same meaning as defined above] Reaction formula (III
), the compound represented by the general formula (1-b) is -Fukudai [
E) and the compound represented by CB) in the presence of a base in a suitable solvent at a temperature range of -10°C to the boiling point of the solvent for 0.5 to 24 hours. It can be produced by oxidizing the compound represented by general formula (F) with an oxidizing agent in the presence of a solvent. - Bases used in the production of compounds represented by CF) include alkali metal amides such as lithium diisopropylamide, alkali metals such as sodium metal and potassium metal, sodium hydride, potassium hydride, and calcium hydride. Alkali metal hydrides and alkaline earth metal hydrides such as, alkali metal carbonates such as sodium carbonate and potassium carbonate, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, organic amines such as triethylamine and pyridine. can be mentioned.

However, if a base is present during the production step of the compound represented by -fukudai [E], it is not necessary to further include a base. In addition, as a solvent, benzene, toluene,
Hydrocarbon solvents such as xylene, halogenated hydrocarbon solvents such as methylene chloride and chloroform, alcohol solvents such as methanol, ethanol and 2-glopanol, ether solvents such as ethyl ether, tetrahydrofuran and dioxane, acetone, methyl ethyl ketone, etc. Ketone solvents, ester solvents such as methyl acetate and ethyl acetate,
Aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, and others such as acetonitrile and water can be used.

Examples of the oxidizing agent for the compound represented by -fukudai [F] used in the production of the compound represented by general formula [1-b] include permanganate, silver oxide, permanganate-periodic acid, etc. can be mentioned. Further, examples of solvents that can be used include water, acetic acid, and mixed solvents of water-acetone and water-acetic acid. The reaction may be carried out for 1 to 24 hours at a temperature ranging from room temperature to the boiling point of the solvent.

Reaction method A [l-c] (1-a) CG) [In the formula, R6 represents a benzyl group which may be substituted with an alkyl group, an alkenyl group, an alkynyl group, a halogen atom or an alkoxy group, Y, + indicates a halogen atom, an imidazolyl group or a group -0COR+o (in the formula, R1° means lower alkyl or phenyl), R, A, B,
X, Yz and Z have the same meanings as defined above] The compound represented by the general formula [:ld] in reaction formula (IV) is the compound represented by -fukudai (1-c) It can be produced by hydrolyzing in water in the presence of an equivalent or more amount of base at room temperature or the boiling point of the solvent for 1 to 48 hours, and then making the reaction solution neutral or acidic with an acid. As the base, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide can be used. Furthermore, alcohols such as methanol and ethanol, and water-soluble organic solvents such as dioxane or acetonitrile may be added for the purpose of speeding up the reaction.

The compound represented by general formula (1-c) in reaction formula (IV) can be produced by esterifying the compound represented by general formula (1-d). Two methods are shown here,
It is not limited to this.

(Method A) By reacting the compound represented by the general formula (1-d) with R and Y2 in the presence of a base in a suitable solvent at a temperature range from room temperature to the boiling point of the solvent for 1 hour to 24 hours. A compound represented by the general formula [1-c] can be produced. Bases include alkali metal carbonates such as sodium carbonate, potassium carbonate, sodium hydroxide, and potassium hydrogen carbonate, alkali metal hydrides such as sodium hydride and potassium hydride, and organic amines such as triethylamine, pyridine, and DBU. can be used. Examples of solvents include hydrocarbon solvents such as benzene, toluene, and xylene; ethers such as ethyl ether, ethylene glycol dimethyl ether, tetrahydrofuran, and dioxane; Aprotic polar solvents such as carbon dioxide, acetonitrile, etc. can be used. In addition, crown ether as a catalyst,
It is also possible to use N N, N'N'-tetramethylethylenediamine and the like.

(Method B) Using the compound represented by the general formula (1-d) and a suitable reaction reagent, the compound represented by CG) is produced, isolated or not, and then R, React with OH, -
This is a method for producing the compound represented by Fukudai (1-c). Here, examples of the reaction reagent used to obtain the compound represented by CG) include thionyl chloride, oxalic acid dichloride, chlorocarbonate, and carbonyldiimidazole. Examples of solvents include hydrocarbon solvents such as benzene, toluene, and xylene, halogenated hydrocarbon solvents such as methylene chloride and chloroform, ethers such as ether, ethylene glycol dimethyl ether, and tetrahydrofuran, N,N-dimethylformamide, and acetonitrile. Aprotic polar solvents can be used,
0.5 to 24 hours at a temperature range from 0 °C to the boiling point of the solvent.
General formula (1-c) by reacting with R,OH for a time
A compound represented by can be produced.

Reaction formula ('/) (l-a) [l-e] (wherein, M″+ and 1/p/* represent a cation such as an alkali metal, an alkaline earth metal, a transition metal, or an organic amine. Also, P and P' are l~ due to the charge of the cation.
3) In the reaction formula (V), the compound represented by the general formula C1-e') is prepared by combining the compound represented by the general formula (1-d) and a base in a solvent within a temperature range of room temperature to the boiling point of the solvent. So, 5 minutes to 10
It can be produced by reacting for a period of time. Examples of solvents include hydrocarbon solvents such as benzene, toluene, and quinoa, halogenated hydrocarbon solvents such as methylene chloride and chloroform, alcohols such as methanol and ethanol, ethyl ether, ethylene glycol dimethyl ether, tetrahydrofuran, and dioxane. Examples include ether solvents, ketone solvents such as acetone and methyl ethyl ketone, ester solvents such as methyl acetate and ethyl acetate, and acetonitrile and water. Bases include alkali metals such as sodium metal and potassium metal, alkali metal hydrides and alkaline earth metal hydrides such as sodium hydride, potassium hydride, and calcium hydride, carbonates such as sodium carbonate, potassium carbonate, and calcium carbonate. Salts, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, and other primary, secondary and tertiary organic amines can be used. Also, -clothing cost (1-e)
The compound represented by 1-1 can be produced by subjecting the compound represented by 1-1 to cation exchange in the above solvent at a temperature ranging from room temperature to the boiling point of the solvent for 5 minutes to 10 hours.

Reaction formula (Vl) (In the formula, R″ and R″′ represent a hydrogen atom or an alkyl group, and A, B, and 2 have the same meanings as defined above.) The compound represented by (1-h) is obtained by hydrolyzing the compound represented by (1-g) in water in the presence of an equivalent or more amount of base, and then making the reaction solution neutral or acidic with an acid. It can be manufactured by Alkali metal hydroxides such as sodium hydroxide and potassium hydroxide can be used as the base. Furthermore, the aforementioned water-soluble organic solvent can be added to speed up the reaction.

Next, the method for producing the intermediate used in the present invention is as follows.

Among the compounds represented by the above formula (A), compounds in which X is an acid atom can be obtained by conventional methods. For example, from the corresponding ketones to Darzens
) reaction to produce oxiranes, and then organic synthesis (Org, Syn,) I[I, No. 73
It can be obtained by hydrolyzing aldehydes as cyanohydrins according to the method described on page 3 (1955).

Further, a compound in which X is a sulfur atom can be obtained, for example, by reacting the corresponding carboxylic acid with sulfur to form a mercapto compound.

The compound represented by the general formula (C) is, for example, an organic synthase (Org, Syn,),
It can be obtained by halogenation according to the method described on page 848 (1955).

The compound represented by the above-mentioned -Fukudai (1) obtained in this way can be applied to barnyard grasses, cypress grasses, cypress grasses, foxtail grasses, morocones, daisies, and staghorn grasses that occur in fields,
Inochi grass, Umanochahiki, Sparrow grass, Sparrow grass, Oat grass, Italian rye grass,
Annual weeds such as Japanese knotweed, Japanese knotweed, Japanese knotweed, pigweed, Japanese chickweed, Japanese fir tree, black-and-white chickweed, golden weed, yellow-bellied grass, common bindweed, wild mustard, European bindweed, datura, common weed, black-and-white weed, blackberry, freckle weed, American helium, and other annual weeds, as well as commonweed, johnson grass, and silverweed. ,
Perennial weeds such as grasshopper can be effectively controlled. In addition, it is also possible to effectively control annual weeds that occur in rice fields, such as Japanese grasshopper, Japanese cypress, Japanese cypress, Japanese cypress, Japanese cypress, and perennial weeds such as Japanese cypress, Japanese cypress, and black cypress. On the other hand, cultivated crops, especially cotton,
It is suitable as an agricultural herbicide because it is highly safe for soybeans.

When the compound represented by (1) above is used as a herbicide, the compound may be used alone or in addition to carriers, surfactants, dispersants, and adjuvants commonly used in the formulation of agricultural chemicals. They can be formulated into various forms such as aquariums, granules, emulsions, or powders.

Examples of carriers used in formulation include solid carriers such as dicrite, talc, bentonite, clay kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, and urea, inglobil alcohol, xylene, cyclohexanone, and methyl. Examples include liquid carriers such as naphthalene. Examples of surfactants and dispersants include alcohol sulfate ester salts, alkylaryl sulfonates, lignin sulfonates, polyoxyethylene glycol ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene sorbitan monoalkylates, and the like. It will be done. Examples of the adjuvant include carboquine methylcellulose, polyethylene glycol, gum arahia, and the like. When using it, either dilute it to an appropriate concentration and spray it, or apply it directly.

Moreover, the herbicide of the present invention can also be used in combination with other herbicides.

The herbicide of the present invention can control many weeds that occur in fields by treating soil or foliage before or after germination of the weeds.

In addition, many weeds that occur in rice fields can be controlled by subjecting the soil to water or treating the foliage before or after the germination of the weeds.

The herbicide of the present invention contains 1 g of active ingredients per 10 are.
Apply ~lhg, preferably 1g~4009.

When spraying on plant foliage, l ppm-10,00
01) l) Dilute to 1'1 and apply.

EXAMPLES Next, the present invention will be explained by examples, but these are not intended to limit the present invention.

Reference Example 1 Method for producing 3-phenyl-3-methyl-2-mercaptobutyric acid 15.2 g of diisopropylamine was added to dried tetrahydrofuran 500IIIQ, and the mixture was heated at -30°C to -40°C.
While stirring at °C, n-butyllithium hexane solution (15%) 849 was added dropwise. After the dripping is complete, add another 30
After stirring for a minute, the temperature was returned to 0°C. After stirring at OoC for 30 minutes, the temperature was again raised to -30 to -40°C, and 17.8 g of 3-7enyl-3-methylbutyric acid and 11 hexamethylphosphoric acid triamide dissolved in 50 mL of tetrahydrofuran were added.
, 6mQ was added dropwise. After stirring for 1 hour, the mixture was brought to 0°C and stirred for another 1 hour. It was then cooled to -to'c and 3.29 g of sulfur powder was added. The temperature was gradually raised to room temperature and stirred overnight. Water was added to the reaction solution, acidified with an aqueous citric acid solution, and the organic phase was dried over anhydrous sodium sulfate and concentrated to obtain a brown solid. Activate this:
Zinc powder 79 was added to 70 mQ of acetic acid and heated under reflux for 6 hours. The reaction solution was poured into water, and the precipitated zinc complex was filtered off.

This complex was dissolved in a 48% aqueous sodium hydroxide solution at 90°C.
I stirred it for 30 minutes. The reaction solution was poured into water, and the filtrate was made acidic with hydrochloric acid and extracted with chloroform.

The plated phase was washed with water, dried over anhydrous sodium sulfate, and concentrated to give 3-phenyl-3-methyl-2-mercaptobutyric acid9.
6g was obtained. Melting point 70-73°C0 Reference Example 2 Method for producing 3.3-dimethyl-2-mercaptobutyric acid Same as Reference Example 1 except that 3.3-dimethylbutyric acid was used instead of 3-phenyl-3-methylbutyric acid. 9.2 g of 3,3-dimethyl-2-mercaptobutyric acid was obtained.

Melting point 80-81'C.

Production method of Example 1 4.5 g of ethyl 2-hydroxy-3-methyl-3-phenylbutyrate, 4.6 g of 4.6-simethoxy-2-methylsulfonylpyrimidine, 5.3 g of anhydrous potassium carbonate, N,
50+ml of N-dimethylformamide (2 in a round bottom flask!') and stirred at 100°C for 3 hours. The reaction mixture was then poured into ice water and extracted twice with 50 mff of ethyl acetate. This extract was washed with water and then dried over anhydrous sodium sulfate overnight. After filtering off the inorganic salt, the solvent was distilled off under reduced pressure to obtain 7 g of crude crystals. This was recrystallized from ethanol to obtain 5.6 g of the target compound.

Melting point: 123-124°C0 Example 2 Preparation method 2-(4,6-Simethoxypyrimidin-2-yl)oxy-3-methyl-3-phenylbutyrate ethyl 4.8 g, 1
0% sodium hydroxide aqueous solution 111112. 50ml of ethanol (I) was placed in a round bottom flask and reacted under reflux for 2 hours, then most of the ethanol was distilled off under reduced pressure. 50+12 of water was added to this residue, and after extracting and removing neutral organic matter with chloroform, Adjust the pH to 3-4 with % hydrochloric acid and add 50mQ
The mixture was extracted twice with ethyl acetate. This extract was washed with water and then dried over anhydrous sodium sulfate overnight. After filtering out the inorganic salts,
The solvent was distilled off under reduced pressure to obtain crude crystals 4, Og. This was recrystallized from ethanol to obtain the target compound 2.89. Melting point 163-165°C0 Example 3 1 g of 3-(3-chlorophenyl)-2-(4,6-cymethoxypyrimidin-2-yl)oxy-3-methylbutyric acid
was dissolved in 10 mQ of a7ton, and 0.69% of 28% sodium methoxide was added thereto. After stirring at room temperature for 1 hour, the precipitated crystals were filtered off to obtain 0.9 g of the target compound. Melting point 220-226°C.

Example 4 2-(4,6-Simethoxypyrimidin-2-yl)oxy-3-methyl-3-(3-methylphenyl)butyric acid 1.
19, anhydrous potassium carbonate 0.5g, glopargyl bromide 0
．． 5g of N,N-dimethylformamide (20mQ) was taken into a 7 round bottom flask and stirred at 80°C for 4 hours. The reaction mixture was then poured into ice water and extracted twice with 50 ml of toluene. This extract was washed with water and then dried over anhydrous sodium sulfate overnight. After filtering off the inorganic salts, the solvent was distilled off under reduced pressure to form a viscous liquid (1.2)? I got it.

When this is dissolved in rhohexane and left at room temperature, crystals will precipitate, and these will be filtered out to yield 0.9 g of the desired metal product.
was gotten. Melting point 95-97°C0 Example 5 2.1 g of methyl 2-hydroxy-3-methyl-3-phenylbutyrate, 1.89 g of 2-chloro-4,6-simethoxys-triazine, and 1.7 g of potassium carbonate were dissolved in 50 tnQ of acetonitrile. and heated under reflux for 20 hours. After cooling the reaction solution, it was poured into water and extracted with 100mA of ethyl acetate.

The organic phase was washed twice with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained liquid substance was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate-〇:l) to obtain the target compound 1.29. Melting point 85-87°C0 Example 6 Production method Methyl 2-hydroquino-3,3-dimethylbutyrate 2.9 g
, 4.19 g of 4.6-dimethyl-2-methylsulfonylpyrimidine, and 3.3 g of potassium carbonate were added to 50 mQ of dimethylformamide and stirred at 100°C for 4 hours. The reaction solution was cooled to room temperature, poured into water, and diluted with ethyl acetate loOm.
12 and the organic phase was washed twice with brine. After drying with sodium sulfate and concentrating under reduced pressure, the obtained liquid substance was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate-6=1) to obtain the target compound 4.
2g was obtained. Refractive index aperture. ” 1.4868゜Example 7 1.5 g of methyl 2-(4,6-trimethylpyrimidin-2-yl)oxy-3,3-dimethylbutyrate was dissolved in 1 methanol.
An aqueous solution lOmQ containing 0.5 g of potassium hydroxide dissolved in Om (1) was added. After stirring at room temperature for 12 hours, 20 mQ of toluene and 30 mQ of water were added and the mixture was carefully mixed in a separatory funnel. The aqueous phase was diluted with oxalic acid. Acidified with aqueous solution, 100ml
Extracted with 2 ethyl ether. The organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the target compound 1.29. Melting point: 167-169°C0 Example 8 13.09 g of 2-hydroquine-3,3-dimethyl-γ-butyrolactone and 24.0 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine were added to 27.0 g of potassium carbonate. 9 in 80 mQ of N,N-dimethylformamide in the presence of h.
Stir at 0°C to 100°C for 3 hours. After cooling to room temperature, it was poured into ice water and extracted with ethyl ether. The extract was washed three times with water and dried over anhydrous magnesium sulfate.

After removing the desiccant by filtration, the filtrate was concentrated to obtain 26.0 g of the target compound.
I got it. Melting point: 139-142°C.

Production method of Example 9 2-(4,6-Simethoxypyrimidin-2-yl)oxy/3.3-dimethyl-γ-butyrolactone 5.4g ethanol 15mQ solution, sodium hydroxide 1.2g water 20mQ The solution was added and stirred at room temperature for 1 hour. Ethanol was removed under reduced pressure, the pH was adjusted to 2 to 3 with 5% hydrochloric acid, and the mixture was extracted twice with ethyl acetate. After washing three times with saline, it was dried over anhydrous magnesium sulfate. After filtering off the desiccant,
The filtrate was concentrated under reduced pressure to obtain the target compound 479. Melting point: 104-110°C.

Example 10 2-hydroxy-4,6-dimethoxypyrimidine 3.5
g, 2-70 methyl mohexanoate 4.79, N,N-dimethylformamide 50 ml (l and anhydrous potassium carbonate 3
．． 3g was stirred at 85-90°C for 3 hours. The reaction mixture was diluted with soaked water cooled to room temperature, and the aqueous mixture was extracted with ethyl ether. After washing the ethyl ether extract with water and drying, the ethyl ether was removed by vacuum distillation to obtain a pale yellow oil. The pale yellow oil was purified by gel column chromatography (elution solvent: hexane:ethyl acetate-61) to obtain the target compound 4.79. Refractive index n. '.

1.4868゜Example 11 Preparation method Diisopropylamine 3.39 and 15% loobyllithium hexane solution 14. 2.3 g of isobutyronitrile and 2.19 crotonaldehyde were added to the tetrahydrofuran solution of lithium diisopropylamide prepared from 10°C.
By sequentially adding C and reacting, 5-cyano-4-
Hydroxy-5-methyl-2-hexene is obtained. 6.5 g of 4.6-dumedel-2-methylsulfonylpyrimidine was added to this reaction solution and stirred overnight.

The mixture was neutralized with a 10% aqueous hydrochloric acid solution, extracted with ethyl acetate, washed with water, and dried. The solvent was distilled off to give 5-cyano-4=(4,6-
Crystals of cymethoxypyrimidin-2-yl)oxy-5-methyl-2-hexene (melting point 91-92°C) were obtained.

The obtained crystals were dissolved in 100 mQ of acetone, and an aqueous solution of 1.79 g of potassium permanganate was added at room temperature and stirred for 1 hour. After distilling off the acetone, the residue was extracted with ethyl acetate, washed, and pi was adjusted to 4 to obtain the target compound (0.6 h). Melting point 142-150°C0 Example 12 Loss of water 2-mercapto-4,6-cymethoxypyrimidine 4.0
g, ethyl 2-bromocyclopentyl acetate4. h,N,
50 mQ of N-dimethylformamide and 349 mQ of anhydrous potassium carbonate were stirred at 90°C for 3 hours. The reaction mixture was diluted with soaked water cooled to room temperature, and the aqueous mixture was extracted with ethyl ether. After washing the ethyl ether extract with water and drying, the ethyl ether was removed by distillation under reduced pressure to obtain a yellow oil. The yellow oil was purified by silica gel column chromatography (elution solvent: hexane: ethyl acetate =
6:1) to obtain 3.6 g of the target compound. Refractive index n. ” 1.5310゜Example 13 Ethanol 20mQ, water 20mQ, sodium hydroxide 0
．． 49, add 2.5 ethyl 2-(4,6-cymethoxypyrimidin-2-yl)thiocyclopentyl acetate.
9 was added and stirred at 45-50°C for 3 hours. Ethanol was removed by vacuum distillation and the residue was extracted with toluene. Remove the toluene phase and adjust the aqueous phase to pH 2~ with 5% hydrochloric acid water.
3 and extracted with ethyl ether. After washing the ethyl ether extract with water and drying, the ethyl ether was removed by vacuum distillation to obtain a white solid. By recrystallizing this solid from isopropyl ether, 16 g of the target compound was obtained. Melting point 125-127°C0 Example 14 2-(
4,6-Simethoxypyrimidin-2-yl)oxy-3
, 3-dimethylbutyric acid was dissolved to prepare the sodium salt. A solution of 1.1 g of iron trichloride (hexahydrate) in 5 ml of water was added to this at room temperature. The precipitated salt was filtered off, thoroughly washed with water, and dried to obtain the desired product 1.19. Melting point 17
8-181'C.

Example 15 Metachloroperbenzoic acid 5.9 in 70 mQ methylene chloride
7.4 g of ethyl 2-(4,6-cymethoxypyrimidin-2-yl)oxy-2-(1-cyclohexenyl)acetate was added to the suspension of 10 g at 5-10° C. over 30 minutes. . The reaction mixture was stirred at room temperature for 12 hours, and the formed crystals were filtered off, and the filtrate was washed several times each with dilute aqueous sodium carbonate solution and water. After drying over anhydrous sodium sulfate, methylene chloride was removed by vacuum distillation to yield a yellow residue. This product was purified by silica gel column chromatography (elution solvent: hexane: ethyl acetate-02l) to obtain 1.9 g of the target compound. Melting point 108~1
10'C! .

Example 16 2-Mercapto-4,6-simethoxypyrimidine 3.2
g, 2-bromo-2-(2,4-dimethylcyclopentyl)ethyl acetate 4.99, N,N-dimethylformamide 50I+la and anhydrous potassium carbonate 2.7 g from 85 to
Stir at 90°C for 3 hours. After the reaction mixture was cooled to room temperature, it was diluted with water and the aqueous mixture was extracted with ethyl ether. After washing the ethyl ether extract with water and drying, the ethyl ether was removed by vacuum distillation to obtain a pale yellow oil. The pale yellow oil was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate-1).
0:1) to obtain 4.5 g of the target compound.

Refractive index n0''1.5202° Example 17 Quin-3-trifluoromethylbutyric acid (compound number 376
) Manufacturing method: 50 mQ of methanol, 50 mQ of water, 1 part of sodium hydroxide.
．． 8.0 g of methyl 2-(4,6-cymethoxypyrimidin-2-yl)oxy-3-trifluoromethylbutyrate was added to the mixed solution of No. 09 and mixed at 45 to 50°C for 4 hours. Methanol was removed by vacuum distillation and the residue was extracted with toluene. The toluene phase was removed, the aqueous phase was adjusted to pH 2-3 with 5% hydrochloric acid, and extracted with ethyl ether. After washing the ether extract with water and drying, ethyl ether was removed by vacuum distillation to obtain a pale yellow solid. This solid is n-
By recrystallizing from hexane, the target compound 5,
9g was obtained. Melting point 112-114°C0 Example 18 2-Mercapto-4,6-dimethoxypyrimidine 10.
49. 15.0 g of ethyl 2-(1-enclopentenyl)-2-(methylsulfonyloxy)acetate, N,N-dimethylformamide loo+m(!), and 9.2 g of anhydrous potassium carbonate were stirred at 90°C for 5 hours. After the reaction mixture was cooled to room temperature, it was diluted with water, and this aqueous mixture was extracted with ethyl ether.The ethyl ether extract was washed with water, dried, and the ethyl ether was removed by vacuum distillation to obtain a yellow oil. The yellow oil was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate-10:l) to obtain the target compound 9.79. Refractive index: 1.5482° Example 19 Production method 2 - A solution of 6.6 g of 2-chloro-4,6-dimethoxy-S-triazine in 30 m of acetone is added to a mixed solution of 6.09 mercapto/clopentyl acetic acid, 4.2 g of potassium hydroxide, and 50 m of water at 0 to 5°C. and added for 20 minutes.

The reaction mixture was then stirred at room temperature for 1.5 hours. Acetone was removed by vacuum distillation and the residue was extracted with ethyl ether. Ethyl ether was removed, the aqueous phase was adjusted to pH 2-3 with 5% hydrochloric acid, and extracted with ethyl acetate. After washing the ethyl acetate extract with water and drying, ethyl acetate was removed by vacuum distillation to obtain a white solid. This solid was recrystallized from isopropyl ether and n-hexane to obtain the target compound 4.
．． I got 59.

Melting point 106-110°C Example 20 2-(4,6-simethoxypyrimidin-2-yl)thione clopentyl acetic acid 5.0 g, incloviramine 1.
09. A mixed solution of 80 mQ of methanol was stirred at room temperature for 1.5 hours. Remove methanol by vacuum distillation,
Isopropyl ether was added to the residue and stirred at room temperature for 5 hours. The generated crystals were collected by filtration, washed with n-hexane, and dried to obtain 4.3 g of the target compound.

Melting point 68-73°C0 Example 21 2-(4,6-Simethoxypyrimidin-2-yl) 2nd
-(4,6-diftquinpyrimidin-2-yl)okine-3-(2,6-dichlorophenyl)propionic acid 1.
5 g, 0.5 g of ethyl bromide and 0.5 g of potassium carbonate.
69 in 50 mQ of N,N-dimethylformamide solution to 8
Stir at 0°C for 2 hours. The reaction solution was poured into water, extracted with ethyl acetate, and washed with water. After drying, the solvent was distilled off to obtain colorless crystals. Melting point: 130-132°C0 Example 22 Preparation method 2-(1-intanyl)-2-(4,6-diftquinpyrimidin-2-yl)oxyacetic acid methyl 3.8 g, potassium hydroxide 6.2 g, water 60mQ and ethanol 60m
The +2 mixed solution was stirred at room temperature for 5 hours. The solvent was distilled off, and the mixture was extracted with ethyl acetate. Extract with aqueous sodium hydrogen carbonate solution, make the aqueous phase acidic, and then extract with ethyl acetate.
Washed with water and dried. The solvent was distilled off to obtain the target compound 2.49
I got it. Melting point 113-117°C0 Example 23 Methyl 2-(l-indanyl)-2-hydroxyacetate 8
-1 g, 4.6-'; 9.0 g of methoxy-2-methylsulfonylpyrimidine and 6.0 g of potassium carbonate in 10
OrnQN, N-dimethylformamide solution at 100°
The mixture was heated and reacted at C for 5 hours. After the reaction was completed, the reaction solution was poured into water and extracted with ethyl acetate. After washing this extract with water and drying, the solvent was distilled off under reduced pressure, and the resulting residue was subjected to 7 silica gel column chromatography (elution solvent: hexane:
Purification with ethyl acetate = 6:l) yielded the target compound 5.8
I got g. Melting point 93-96°C0 Example 24 2.9 g of methyl 2-(2-methylindan-1-yl)-2-hydroxyiacetate, 2.9 g of 4,6-cymethoxy-2-methylsulfonylpyrimidine and 2 potassium carbonate.
．． A 50m<IN, N-dimethylformamide solution of No. 19 was reacted by heating at 80° C. for 3 hours. After the reaction was completed, the reaction solution was poured into water and extracted with ether. After washing this extract with water and drying, the solvent was distilled off under reduced pressure, and methyl 2-(2-methylindan-1-yl)-2-(4,6-cymethoxypyrimidin-2-yl)oxyacetate .3g was obtained.

Melting point: 102-104°C.

3.2 g of methyl 2-(2-methylindan-1-yl)-2-(4,6-cymethoxypyrimidin-2-yl)oxyacetate thus obtained, 1.09 g of potassium hydroxide
, 100+++Q of water and 100m+2 of acetone were reacted at 60°C for 3 hours. The solvent was distilled off, and the mixture was extracted with ether. Extract with sodium bicarbonate aqueous solution,
After making the aqueous phase acidic, it was extracted with ether, washed with water, and dried. The solvent was distilled off to obtain the target compound 1. I got h. Melting point 1
48~151'C! .

Example 25 3. Process for producing 3-dimethyl-2-(4,6-simethoxys-t) 3. Benzyl 3-dimethyl-2-hydroxybutyrate 4.8
g and 3.4 g of 2-chloro-4,6-simethoxy s-triazine were dissolved in tetrahydro7ran 1OOIIQ,
Stir under water cooling. Sodium hydride (60%) 1.2
g was added, and the mixture was returned to room temperature and stirred overnight. The reaction solution was poured into water, and 80 ram of ethyl acetate was added for extraction. The organic phase was washed with water, dried over sodium sulfate, and concentrated to obtain an oily substance. Purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate-10:l), 3.3
6.2 g of benzyl -dimethyl-2-(4,6-dimethoxy-S-triazin-2-yloxy)butyrate was obtained. Melting point 63-66°C.

The 3,3-dimethyl-2-(4,6-
Moisten 4.59 of benzyl (cymethoxy s-triazin-2-yluoquine) butyrate with 2 mQ of acetic acid and add 0.59 of palladium on carbon (10%) to 100 mQ of ethanol. 257 mQ of hydrogen was added with stirring at room temperature. The reaction solution was filtered, 200 mα of ethyl acetate was added to the filtrate, and the mixture was washed with water three times. The organic phase was dried over sodium sulfate and concentrated under reduced pressure to yield the desired compound 3. I got Ly. Melting point 37
~40℃.

Example 26 Production method 3-phenyl-3-methyl-2-mercaptobutyric a1.9
Dissolve g in acetone 50rRa and add 51IIa under water cooling.
of potassium hydroxide dissolved in water was added. followed by 2-chloro-4,6-dimethoxy-S-triazine 1
．． 59 was dissolved in 20rmQ of acetone and added. Stir for 30 minutes: Afterwards, pour the reaction solution into water and add 50 ml of ethyl acetate.
Ma was added and extracted. The aqueous phase was made acidic by adding an aqueous citric acid solution, and extracted by adding 100 ml of chloroform. The organic phase was washed with water, dried over anhydrous sodium sulfate, concentrated,
2.2 g of the target compound was obtained. Melting point 115-118°C0
Example 27 2-(1,2,3,4-tetrahydronaphthalene-1-
3.0 g of ethyl xo-2-hydroquine-2-(+,2,3.4-tetrahydronaphthalen-1-oxo-2-yl)acetate and 2.6 g of 4,6-cymethoxy-2-methylsulfonylpyrimidine were added to 5Qm of tetrahydrofuran. (Sodium hydride (60%) O,h was added at 5°C. After stirring overnight, the reaction solution was poured into water and extracted with ethyl acetate. It was dried over anhydrous sodium sulfate and concentrated. .

/ Purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate-6:l) to obtain the target compound
I got g.

Next, examples of formulations of the herbicide of the present invention will be shown.

Example 28 (hydrating powder) Compound (1) l 0%, Emulgen 810 (Kao Corporation registered trademark) 0.5%, Demol N (Kao Corporation registered trademark) 0.5%, Kunilite (Kunimi Fu Kogyo Co., Ltd.) A wettable powder was prepared by uniformly mixing and pulverizing Zikrite (registered trademark of Zikrite Co., Ltd.) CA 69% and Zikrite (registered trademark of Zikrite Co., Ltd.) 20120%.

Example 29 (Emulsion) An emulsion was prepared by uniformly dissolving 30% of compound (1), 20% of cyclohexanone, 11% of polyoxyethylene alkylaryl ether, 4% of calcium alkylbenzene sulfonate, and 35% of methylnaphthalene.

Example 30 (granules) Compound (1) 5%, sodium salt of lauryl alcohol sulfate 2%, sodium lignin sulfonate 5%
, carboxymethyl cellulose 2%, and clay 86%
Mix and grind evenly. 100 parts by weight of this mixture and 2 parts water
Add 0 parts by weight, knead, and use an extrusion granulator to make 14~
After processing into 32 mesh granules, the mixture was dried to form granules.

Example 31 (Powder) 2% of compound (1), ±5% of diatomaceous matter, and 93% of clay were uniformly mixed and ground to obtain a powder.

Next, the herbicidal effects of the herbicide of the present invention will be explained by giving examples in which the herbicide of the present invention is applied to various plants.

In addition, in the following examples, abbreviations in the table represent the following plants.

EC, barnyard grass (Echinochloa crus-ga)
li) Dl; Media/Bas (Digitalia ads
cendens) PO;
um nodosum) Δm: Amaran
thus retroflexus) Ch;
henopodium album) C1; Cyperus 1ria Cd, Cyperus difformis MO: Monochoria vaginalis SC:
Scirpus hotarui Se; Setaria viridis So;
Johnson grass (Sorghum halepens)
e) GO; Gossypium hirsutu
m) G1. Soybean (Glycine max) Application Example 1 In a 100 cm" pot filled with soil, each seed of Japanese barnyard grass, Japanese knotweed, Aobiyu, Glycine max, and Glycine japonica were sown, and the seeds were covered with soil to a thickness of 0.5 to 1 crR.

After growing the pot in a glass room at 20-25°C for 2 weeks, dilute the hydrating agent prepared according to Example 28 with the active ingredient to 4009 per 10 are with 100 Q of water per 10 are, and apply it on the stem and leaf surface. Spread. The investigation was conducted after 14 days of drug treatment.
The test was carried out on Day 1 according to the standards in Table 1. The results are shown in Table 2 as an index.

Table 1 Application Example 2 Seeds of Japanese barnyard grass, Japanese knotweed, Japanese knotweed, Japanese violet, N. rosa, and Japanese cypress were sown in a 10oc+++' pot filled with soil, and 0.5 to 1 cm of 1:N soil was seeded.

On the day after sowing, a hydrating agent prepared according to Example 28 was diluted with 1 ook of water per 10 ares to give an active ingredient of 400 g per 10 ares, and the mixture was sprayed on the soil surface. The investigation was conducted 20 days after the drug treatment according to the criteria listed in Table 1.

The results are shown in Table 3 as an index.

Table 3 Application Example 3 Two 100 cm pots were filled with paddy soil, and after puddling, each seed of Japanese barnyard grass, Japanese cypress, Japanese cypress, and firefly were sown, and the pots were flooded with 5 cm of water. Example 281 two days after sowing:
The active ingredient of the hydrating agent prepared by
It was diluted with water to a total weight of 0 g and dropped onto the water surface. Table 4 shows the results of the survey conducted on day 21 after the drug treatment according to the criteria in Table 1 as an index.

Application example 4: 600cm pot filled with soil.
Seeds of Oza and cotton were sown and covered with soil to a thickness of 0.5 to 1 cm. On the day after sowing, a predetermined amount of the hydrating agent prepared according to Example 28 was diluted with +0012 water per 10 ares and sprayed on the soil surface. The herbicidal effect was determined according to the standards in Table 1, and the chemical damage was determined according to the standards in Table 5, 20 days after the chemical treatment. The results are shown in Table 6 as an index.

Table 5 (Application Example 5) This test was conducted in the same manner as in Application Example 4 except that the crop was replaced with soybean, and the results are shown in Table 7 as an index.

Claims (1)

[Claims] 1 General formula ▲ Numerical formula, chemical formula, table, etc. It is an amino group, and R and R' may be bonded to each other to form a lactone ring, and A is a halogen atom, an alkyl group, an alkoxy group, a halogen-substituted alkyl group, a halogen-substituted alkoxy group, an alkylthio group, An amino group or a substituted amino group, B is a hydrogen atom, an alkyl group, an alkoxy group, a halogen-substituted alkyl group, or a halogen-substituted alkoxy group, X is an oxygen atom or a sulfur atom, and Z is a methine group or a nitrogen atom) A herbicide containing an alkanoic acid derivative or its salt as an active ingredient. 2 General formula▲There are mathematical formulas, chemical formulas, tables, etc.▼ (R_1 in the formula is a hydrocarbon group or substituted hydrocarbon group, R_
1' is a hydrogen atom, a hydrocarbon group, or a substituted hydrocarbon group, R_1 and R_1' may be bonded to each other to form a lactone ring, and A_1 is a halogen atom, an alkyl group, an alkoxy group, an alkanoic acid derivative represented by a halogen-substituted alkyl group, a halogen-substituted alkoxy group, an alkylthio group, an amino group or a substituted amino group, B_1 is a hydrogen atom, an alkyl group, an alkoxy group, a halogen-substituted alkyl group, or a halogen-substituted alkoxy group; That salt. 3 General formula▲There are mathematical formulas, chemical formulas, tables, etc.▼ (R_2 in the formula is a hydrocarbon group with 3 or more carbon atoms, R_2'
is a hydrogen atom, a hydrocarbon group, a substituted hydrocarbon group, or an alkylidene amino group, A_2 and B_2 are each a group selected from an alkyl group, an alkoxy group, an amino group, and a substituted amino group, and Z is a methine group or a nitrogen atom. an alkanoic acid derivative or a salt thereof represented by 4 General formulas ▲ Numerical formulas, chemical formulas, tables, etc. ▼ A_3 and B_
(3 is a group selected from an alkyl group and an alkoxy group, respectively) or a salt thereof.