JPH0578331A - New halogenated cycloalkanecarboxylic acid derivative and herbicide containing the same derivative as active component - Google Patents

Abstract

PURPOSE:To provide new halogenated cycloalkanecarboxylic acid derivatives showing an excellent herbicidal effect not only for annual weeds but for perennial weeds and excellent in safety to some kinds of crops. CONSTITUTION:Halogenated cycloalkanecarboxylic acid derivatives of formula I [W is halogen; Y is alkoxy, alkenoxy, alkynoxy, (substituted)aryloxy, disubstituted amino, OH, amino, hydroxyamino, alkoxyamino, alkenoxyamino, etc.; When Z<1> is N, Z<2> is N or methine. When Z<1>=methine, Z<2> is N; R<1> and R<2> are halogen, alkyl, (halogenated)alkoxy, mono- or di-substituted amino or alkylthio; (n) is 0 or 1], e.g. methyl 1-fluoro-2-(4,6-dimethoxy-pyrimidinyl-2-thio)-1- cyclohexanecarboxylate. The compound of formula I is obtained, e.g. by reacting a compound of formula II with a compound of formula III (W' is halogen, etc.) in the presence of a base.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel halogenated cycloalkanecarboxylic acid derivative not described in the literature, and a herbicide containing the derivative as an active ingredient.

[0002]

2. Description of the Related Art Japanese Patent Application Laid-Open No. 2-85262 describes an alkanecarboxylic acid having a pyrimidine ring or a triazine ring and a herbicide containing the same.

[0003]

However, the compounds described in the above-mentioned documents have many points to be improved in terms of herbicidal spectrum, dosage amount, selectivity and the like.

The present inventors have conducted extensive studies to develop a compound having a broad herbicidal spectrum, a high herbicidal effect, and excellent safety against crops. As a result, the halogenated cycloalkenecarboxylic acid moiety and a specific substituent are bonded to each other. The halogenated cycloalkenecarboxylic acid derivative of the present invention having a structure in which the pyrimidine ring or triazine ring portion thereof is condensed via a sulfur atom is novel, and this compound is an excellent herbicide against not only annual but also perennial weeds. In addition to showing the effect, they have found that they have high safety against certain kinds of crops, and have completed the present invention.

[0005]

The compound of the present invention has the following general formula (I):

[0006]

[Chemical 3]

[In the formula, W represents a halogen atom. Y is a lower alkoxy group, a lower alkenoxy group, a lower alkynoxy group, an optionally substituted aryloxy group, a di-substituted amino group which may form a ring structure by combining mono or two substituents, a hydroxy group and The agriculturally acceptable salt, amino group, hydroxyamino group, lower alkoxyamino group, lower alkenoxyamino group, lower alkynoxyamino group, or optionally substituted aryloxyamino group is shown. Z ¹ and Z ² are, when Z ¹ is a nitrogen atom, Z ² is a nitrogen atom or a methine group,
When Z ¹ is a methine group, Z ² represents a nitrogen atom. R ¹ and R ² are each independently a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxy group substituted with a halogen atom, or a mono- or two-substituents bonded to each other to form a ring structure. A substituted amino group or a lower alkylthio group is shown. n represents 0 or 1. ] The novel halogenated cycloalkanecarboxylic acid derivative represented by

In the above general formula (I), W represents a halogen atom, preferably fluorine or chlorine, and particularly preferably fluorine. Y is a lower alkoxy group, a lower alkenoxy group, a lower alkynoxy group, an optionally substituted aryloxy group, a di-substituted amino group which may form a ring structure by combining mono or two substituents, and a hydroxy group. And its agriculturally acceptable salts, amino groups, hydroxyamino groups, lower alkoxyamino groups, lower alkenoxyamino groups, lower alkynoxyamino groups, optionally substituted aryloxyamino groups, or benzyloxy. A group is shown, and among these, a methoxy group, an ethoxy group, a hydroxy group, an allyloxy group, a propargyloxy group, or an ammonium salt is preferable.

R ¹ and R ² may be combined with a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxy group substituted with a halogen atom, a mono- or two substituents to form a ring structure. A di-substituted amino group or a lower alkylthio group is shown, and among these, a methoxy group, a difluoromethoxy group, an ethoxy group, a chlorine atom, a methylthio group or a dimethylamino group is preferable.

In the above general formula (I), W, Y, R ¹
Specific examples of each group and atom in the definition of R ² and R ² are shown below.

[0011]Halogen atomFluorine, chlorine, bromine, or
Is iodineLower alkyl group For example, methyl, ethyl, propyl,
Isopropyl, butyl, isobutyl, secondary butyl, tertiary
Butyl, isopentyl, neopentyl, tertiary pentyl
And hexyl, heptyl, octyl, or their variants.
Sex, etc.Lower alkoxy group ; For example, methoxy, ethoxy, pro
Poxy, butoxy, isopropoxy, isobutoxy, no.
2-butoxy, or tertiary butoxy, etc.Lower alkenoxy group ; For example, vinyloxy, allyl
Xy or isopropenyloxy etc.Lower alkynoxy group ; For example, ethynyloxy or
Lopargyloxy, etc.Optionally substituted aryloxy group ; For example, Fe
Noxy, toluyloxy, mesityloxy, fluoro
Enoxy or chlorophenoxy etc.Mono or two substituents combine to form a ring structure
Optionally substituted di-substituted amino group ; For example, methylamino, ethi
Lumino, propylamino, isopropylamino, dime
Tylamino, diethylamino, 1-pyrrolidinyl or
1-piperidino etc. Salt when Y is a hydroxy group For example, sodium, potassium, ammonium, isop
Such as ropyl ammonium or triethyl ammonium
Agrochemically acceptable saltLower alkoxyamino group ; For example, methoxyamino, eth
Xyamino, propoxyamino or isopropoxya
Mino, etc.Lower alkenoxyamino group ; For example, vinyloxyami
No, allyloxyamino or isopropenyloxya
Mino, etc.Lower alkynoxyamino group ; For example, ethynyloxya
Mino or propargyloxyamino etc.Aryloxyamino group which may be substituted ;example
For example, phenoxyamino, toluyloxyamino, mesit
Luoxyamino, fluorophenoxyamino or black
Rofenoxyamino, etc.Lower alkoxy group substituted with halogen atom ; For example,
Monofluoromethoxy, difluoromethoxy, triflu
Oromethoxy, chloromethoxy, dichloromethoxy, or
Or 2,2,2-trifluoroethoxy, etc.Lower alkylthio group ; For example, methylthio, ethylthio
Oh, propylthio, or isopropylthio, etc.
The optically active substance of the compound represented by the general formula (1) is
It should be understood that it is included within the scope of light.

The compounds of the present invention represented by the above general formula (I) are shown in Table 1.

[0013]

[Table 1]

[0014]

[Table 2]

[0015]

[Table 3]

The compound of the present invention can be produced, for example, by the following methods A, B and C.

[0017]

[Chemical 4]

[Wherein W, X, Z ¹ , Z ² , R ¹ , R ² and n have the same meanings as described above, W'is a halogen atom,
A lower alkylsulfonyl group or an arylalkylsulfonyl group is shown. In the above reaction scheme, the compound represented by the formula (I) is obtained by reacting the halogenated cycloalkanethiol derivative of the above formula (II) with or without a solvent in the presence of a suitable base at −78 ° C. To the temperature range of the boiling point of the solvent,
It can be produced by reacting with the substituted pyrimidine or triazine of the above formula (III) for 1 to 24 hours.

When a solvent is used in this reaction, examples thereof include hydrocarbon solvents such as benzene, toluene and xylene; halogenated hydrocarbon solvents such as dichloromethane and chloroform; diethyl ether, diisopropyl ether and tetrahydrofuran. , 1,4-
Ether solvents such as 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, dimethylsulfoxide, dimethylacetamide; acetonitrile, water, etc. You can

As the base, carbonates such as sodium carbonate and potassium carbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; metal alkoxides such as sodium methoxide and sodium ethoxide; sodium hydride, Alkyl metal hydrides such as potassium hydride; lithium amides such as lithium diethylamide, lithium diisopropylamide and lithium bistrimethylsilylamide can be mentioned.

Method B

[0022]

[Chemical 5]

[Wherein W, Y, Z ¹ , Z ² , R ¹ , R ² and n have the same meanings as described above, and M represents an alkali metal, alkaline earth metal or organic amine cation. In the above reaction scheme, the compound represented by the formula (IV) is a compound represented by the formula (I) with a suitable base in the presence of a suitable solvent at room temperature to a boiling point of the solvent within a temperature range of 1 to 1.
It can be produced by reacting for 24 hours.
Further, the compound represented by the formula (IV) can be produced by treating the compound represented by the formula (IV) with an acid. Examples of the solvent used in this 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, chloroform; diethyl ether. , Ether solvents such as diisopropyl ether, tetrahydrofuran, 1,4-dioxane; ketone solvents such as acetone and methyl ethyl ketone; ester solvents such as methyl acetate and ethyl acetate; aprotic substances such as dimethylformamide, dimethylsulfoxide, dimethylacetamide A polar solvent; acetonitrile, water, etc. can be mentioned.
Examples of the base 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 alkoxides such as sodium methoxide and sodium ethoxide; water. Examples thereof include alkyl hydride metals such as sodium oxide and potassium hydroxide.

Method C

[0025]

[Chemical 6]

[In the formula, W, Y, Z ¹ , Z ² , R ¹ , R ² and n have the same meanings as described above. T represents a hydroxyl group or a halogen atom. In the above reaction scheme, the compound represented by the formula (I) is obtained by using the carboxylic acid of the formula (V) with a suitable condensing agent in the presence of a suitable halogenated hydrocarbon or alcohol and no solvent or a suitable solvent. , −78 ° C. to the boiling point of the solvent for 1 to 24 hours. Examples of the solvent used in the reaction include hydrocarbon solvents such as benzene, toluene and xylene; dichloromethane,
Halogenated hydrocarbon solvents such as chloroform; ether solvents such as diethyl ether, diisopropyl ether, tetrahydrofuran, 1,4-dioxane; ketone solvents such as acetone and methyl ethyl ketone; ester solvents such as methyl acetate and ethyl acetate; dimethyl Aprotic polar solvents such as formamide, dimethyl sulfoxide, dimethylacetamide; acetonitrile, water and the like can be mentioned. Examples of the condensing agent include carbonates such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate and potassium hydrogen carbonate; metal hydroxides such as sodium hydride and potassium hydride; metal alkoxides such as sodium methoxide and sodium ethoxide; Sodium hydride,
Examples thereof include alkyl hydrides such as potassium hydride; organic bases such as diazabicycloundecene; and dehydration condensation agents such as dicyclohexylcarbodiimide. Next, synthetic examples of the compound belonging to the above formula (I) of the present invention will be explained by way of Examples.

[0027]

【Example】

[0028]

Example 1 1-Fluoro-2- (4,6-dimethoxypyrimidinyl
Methyl 2-thio) -1-cyclohexanecarboxylate
Production of (Compound No. 1) First, Tetrahedron Letters, Vol. 27, No. 37, 4
Ethyl 1-fluoro-2-oxocyclohexanecarboxylate was produced from ethyl 2-oxocyclohexanecarboxylate with reference to the method described on pages 465 to 4468 (1986).

This ethyl 1-fluoro-2-oxocyclohexanecarboxylate was dissolved in methanol, and hydrogen sulfide and hydrogen chloride were simultaneously blown thereinto at -78 ° C for 2 hours.
After further reacting at −10 ° C. for 2 hours, the solvent was distilled off,
This was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate = 20/1) to give 1-
Methyl fluoro-2-mercaptocyclohexanecarboxylate was obtained.

192 mg (1 mmol) of methyl 1-fluoro-2-mercaptocyclohexanecarboxylate and 218 mg (1 mmol) of 4,6-diethoxy-2-methylsulfonylpyrimidine were dissolved in 10 ml of dimethylformamide, and 166 mg of potassium carbonate ( 1.
(2 mmol) was added and the mixture was stirred at room temperature for 5 hours. Reaction mixture 5
It was poured into 0 ml of water, extracted 3 times with 30 ml of ethyl acetate, the obtained organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off to obtain 350 mg of a crudely purified product. This is subjected to silica gel chromatography (developing solvent:
Purify with hexane / ethyl acetate-10 / 1) to give the desired 1-fluoro-2 (4,6-diethoxypyrimidinyl-
257 mg (yield: 78%) of methyl 2-thio) -1-cyclohexanecarboxylate (Compound No. 1) was obtained.

¹ H-NMR (δ, CDCl ₃ ) 5.78
(S, 1H), 3.90 (s, 6H), 3.75 (s, 3)
H), 1.1 to 3.3 (m, 9H) The herbicide of the present invention contains a novel halogenated cycloalkanecarboxylic acid (I) which is a compound of the present invention as an active ingredient.

When the compound of the present invention is used as a herbicide, it is mixed with a carrier or diluent, an additive, an auxiliary agent and the like by a known method to prepare a formulation form usually used as an agricultural chemical, for example, powder, granules, It is prepared and used as a wettable powder, an emulsion, a water solvent, a sol, etc. Further, it can be used in combination or in combination with other agricultural chemicals such as fungicides, insecticides, acaricides, other herbicides, plant growth regulators and fertilizers, soil conditioners and the like. In particular, when used in combination with other herbicides, it not only reduces the amount of the drug used and saves labor, but it is also expected that the synergistic action of both drugs will broaden the herbicidal spectrum and further enhance the synergistic effect. .

As the carrier or diluent, a generally used solid or liquid carrier is used. As solid carriers, kaolinite group, clays represented by montmorillonite group or polygloskite group, etc., specifically, pyroflight, attapulgite, sepiolite, kaolinite, bentonite, vermiculite,
Mica, talc, etc .; gypsum, calcium carbonate, dolomite,
Other 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, crystalline cellulose and other plant organic substances Substances: coumarone resin, petroleum resin, alkyd resin, polyvinyl chloride, polyalkylene glycol, ketone resin, ester gum,
Examples thereof include synthetic or natural polymer compounds such as cobal gum and dammal gum; waxes such as carnauba wax and beeswax, and urea. Suitable liquid carriers include paraffinic or naphthenic hydrocarbons such as kerosene, mineral oil, spindle oil and white oil; aromatic hydrocarbons such as toluene, xylene, ethylbenzene, cumene and methylnaphthalene; trichloroethylene, monochlorobenzene, orthochlor. Chlorinated hydrocarbons such as toluene; ethers of dioxane and tetrahydrofuran; ketones such as acetone, methyl ethyl ketone, diisobutyl ketone, cyclohexanone, acetophenone, isophorone; ethyl acetate, amyl acetate, ethylene glycol acetate,
Esters such as diethylene glycol acetate, dibutyl maleate, diethyl succinate; methanol, n
Alcohols such as 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; polar solvents such as dimethylformamide, dimethyl sulfoxide or Examples include water. In addition, a surfactant or other auxiliary agent may be used for the purpose of emulsification, dispersion, wetting, spreading, binding, adjusting disintegration, stabilizing active ingredient, improving fluidity, rust prevention and the like of the compound of the present invention. .. Examples of surfactants used include nonionic, anionic, cationic and zwitterionic, but usually nonionic and / or anionic Stuff used.

Suitable nonionic surfactants include, for example, compounds obtained by polymerizing addition of ethylene oxide to higher alcohols such as lauryl alcohol, stearyl alcohol and oleyl alcohol; isooctylphenol,
Compounds obtained by polymerizing addition of ethylene oxide to alkylphenols such as nonylphenol; Compounds obtained by polymerizing addition of ethylene oxide to alkylnaphthols such as butylnaphthol and octylnaphthol; Polymerization addition of ethylene oxide to higher fatty acids such as palmitic acid, stearic acid and oleic acid Compounds; higher fatty acid esters of polyhydric alcohols such as sorbitan and compounds obtained by polymerizing addition of ethylene oxide thereto; compounds obtained by block-polymerizing addition of ethylene oxide and propylene oxide.

Suitable anionic surfactants include, for example, alkyl sulphate salts such as sodium lauryl sulphate and oleyl alcohol sulphate amine salts; alkyls such as sodium sulfosuccinate dioctyl ester and sodium 2-ethylhexene sulphonate. Sulfonates; aryl sulfonates such as sodium isopropyl naphthalene sulfonate, sodium methylenebisnaphthalene sulfonate, sodium lignin sulfonate, sodium dodecylbenzene sulfonate, and the like.

Further, in the herbicide of the present invention, for the purpose of improving the properties of the preparation and enhancing the herbicidal effect, polymers such as casein, gelatin, albumin, glue, sodium alginate, carboxymethyl cellulose, methyl cellulose, hydroxyethyl cellulose and polyvinyl alcohol are used. Compounds and other auxiliary agents can also be used in combination.

The above-mentioned carrier and various auxiliary agents are appropriately used alone or in combination depending on the purpose, taking into consideration the dosage form of the preparation, the application scene and the like.

The content of the compound (active ingredient) of the present invention in the various dosage forms thus obtained varies depending on the dosage form, but is usually 0.1 to 99% by weight, and particularly Most preferred is 1 to 80% by weight.

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 balance is a solid carrier and a dispersion wetting agent, and if necessary, a protective colloid agent, a defoaming agent and the like. Added.

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

In the case of an emulsion, for example, the compound as an active ingredient is usually contained in an amount of 5 to 30% by weight, which contains about 5 to 20% by weight of an emulsifier, and the balance is a liquid carrier.
Corrosion inhibitors are added as needed.

In the case of a flowable agent, for example, the compound of the active ingredient is usually contained in an amount of 5 to 50%, a dispersion wetting agent of 3 to 10% by weight is contained therein, and the balance is water, and if necessary, a protective colloid. Agents, preservatives, defoamers, etc. are added.

The novel halogenated cycloalkanecarboxylic acid derivative of the present invention can be applied as it is to the compound of the general formula (I) or in any preparation form as described above. The herbicide of the present invention can be applied to the control or control of various weeds that grow in paddy fields and upland fields from the pre-emergence stage to the growing season. The amount applied is about 0.01 to 5 kg per ha as the amount of the compound represented by the general formula (I) (the amount of active ingredient),
It is preferably about 0.01 to 1 kg, and can be appropriately selected and changed depending on the type of the weed, the growth stage, the application place, the application time, the weather and the like.

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

Formulation Example 1 (Granule) Compound No. 1 5 parts Bentonite 50 parts Talc 40 parts Sodium dodecylbenzene sulfonate 2 parts Sodium lignin sulfonate 2 parts Polyoxyethylene alkylphenyl ether 1 part After thoroughly mixing the above, An appropriate amount of water was added, the mixture was kneaded, and granulated using an extrusion granulator to obtain 100 parts of granules.

Formulation Example 2 (wettable powder) Compound No. 1 20 parts Diatomaceous earth 60 parts White carbon 15 parts Sodium lignin sulfonate 3 parts Sodium dodecylbenzene sulfonate 2 parts Mix the above components and grind with a jet mill to hydrate 100 parts of agent was obtained.

Formulation Example 3 (Emulsion) Compound No. 1 30 parts Xylene 55 parts Cyclohexanone 10 parts Calcium dodecylbenzene sulfonate 3 parts Polyoxyethylene alkylphenyl ether 2 parts The above components were uniformly mixed and dissolved to obtain 100 parts of an emulsion.

Drugs using the compound of the present invention were each prepared according to the above-mentioned preparation examples.

[0049]

The effect of the present invention is represented by the above general formula (I),
The halogenated cycloalkenecarboxylic acid derivative is a novel compound described in the end of the literature. The general formula (I) of the present invention
The compound represented by has a structure in which a structurally extremely simple halogenated cycloalkanecarboxylic acid moiety and a pyrimidine ring or triazine ring moiety to which a specific substituent is bonded are bonded via an oxygen atom. It is considered that the excellent herbicidal action is exhibited due to its structural characteristics.

The compound and the herbicide of the present invention can control various weeds that grow on agricultural land from pre-emergence to growing season. For example, paddy field weeds such as Nobie, Firefly, Mizuhigai, Konagi, Azaena, Mizohabe, Kishigusa, Matsubai, Urikawa, etc., and Crabgrass, Enocorogusa, Ohishiba, Suzumenohe, Suzumetenopia, Amaranthaceae, Amaranthus japonicus, Amaranthus japonicus, Acacia serrata, Acacia, It is possible to control weeds such as morning glory, morning glory, ragweed, ragweed, herb, rapeweed, sengangusa, yaemgra and buckwheat vine. In addition to paddy fields and fields, orchards, mulberry fields,
It can also be used on lawns and non-cultivated lands.

Moreover, the compound of the present invention has selectivity for certain cultivated crops, and particularly excellent selectivity for crops such as cotton, soybean and corn.

Next, the herbicidal effect will be described with reference to test examples.

Test Example 1 (Treatment of Upland Field Leaves) A square pot (30 × 30 × 12 cm) was filled with upland soil, and various crops and various weed seeds shown in Table 2 were sown in fixed amounts, and each plant had 1. It was grown in the greenhouse until the 5th to 3rd leaf stage. The compound of the present invention shown in Table 2 was prepared into a wettable powder according to Formulation Example 2, and the water dilution thereof was applied to each plant at a spraying amount of 5001 / ha so that the amount of active ingredient shown in Table 2 was obtained. Sprayed evenly on the foliage. 2 after applying the drug
One day later, the herbicidal effect on various weeds and the degree of chemical damage to various crops were determined according to the following criteria. The results are shown in Table 3.

[0054]

[Table 4] Test Example 2 (Soil Treatment Before Germination of Upland Field) A square pot (30 × 30 × 12 cm) was filled with upland soil, and various crops and various weed seeds shown in Table 3 were sown in fixed amounts, and then covered with 1 cm of soil. .. The compound of the present invention shown in Table 3 was prepared as a wettable powder according to Formulation Example 2, and the diluted solution was adjusted to 5001 / ha so that the active ingredient amount shown in Table 3 was obtained.
The amount was applied evenly to the soil. Twenty-one days after the chemical spraying, the herbicidal effect on various weeds and the degree of phytotoxicity on various crops were determined according to the criteria of Test Example 1. The results are shown in Table 4.

[0055]

[Table 5]

[0056]

[Table 6]

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁵ Identification code Internal reference number FI Technical indication location C07D 251/22 7019-4C 251/38 7019-4C (72) Inventor Takako Takahashi Ami, Inashiki-gun, Ibaraki Prefecture 8-3-1, Machichuo Sanritsu Petrochemical Co., Ltd., Tsukuba Research Laboratory (72) Inventor Keiji Endo 8-3-1, Chuo, Ami-machi, Inashiki-gun, Ibaraki Sanryo Petrochemical Co., Ltd. ( 72) Inventor Rika Higurashi 8-3-1, Chuo, Ami-machi, Inashiki-gun, Ibaraki Sanryo Yuka Co., Ltd. Tsukuba Research Institute

Claims (2)

[Claims] 1. A compound represented by the general formula (I): [In formula, W shows a halogen atom. Y is a lower alkoxy group, a lower alkenoxy group, a lower alkynoxy group, an optionally substituted aryloxy group, a di-substituted amino group which may form a ring structure by combining mono or two substituents, a hydroxy group and Its agronomically acceptable salt,
An amino group, a hydroxyamino group, a lower alkoxyamino group, a lower alkenoxyamino group, a lower alkynoxyamino group, and an optionally substituted aryloxyamino group are shown. Z ¹ and Z ^2, Z ² when Z ¹ is a nitrogen atom represents a nitrogen atom or a methine group, Z ² when Z ¹ is a methine group refers to a nitrogen atom. R ¹ and R ² are each independently a halogen atom, a lower alkyl group, a lower alkoxy group,
It represents a lower alkoxy group substituted with a halogen atom, a di-substituted amino group which may form a ring structure by combining mono or two substituents, or a lower alkylthio group. n
Represents 0 or 1. ] The novel halogenated cycloalkane carboxylic acid derivative represented by these. 2. A compound represented by the general formula (I): [In formula, W shows a halogen atom. Y is a lower alkoxy group, a lower alkenoxy group, a lower alkynoxy group, an optionally substituted aryloxy group, a di-substituted amino group which may form a ring structure by combining mono or two substituents, a hydroxy group and Its agronomically acceptable salt,
An amino group, a hydroxyamino group, a lower alkoxyamino group, a lower alkenoxyamino group, a lower alkynoxyamino group, and an optionally substituted aryloxyamino group are shown. Z ¹ and Z ^2, Z ² when Z ¹ is a nitrogen atom represents a nitrogen atom or a methine group, Z ² when Z ¹ is a methine group refers to a nitrogen atom. R ¹ and R ² are each independently a halogen atom, a lower alkyl group, a lower alkoxy group,
It represents a lower alkoxy group substituted with a halogen atom, a di-substituted amino group which may form a ring structure by combining mono or two substituents, or a lower alkylthio group. n
Represents 0 or 1. ] A herbicide containing a novel fluorinated cycloalkanecarboxylic acid derivative represented by the following as an active ingredient.