JP2002138075A - 3-aminoacrylic acid derivative and herbicide - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new compound possible to be used for a herbicide that can be advantageously synthesized industrially and has definite effect even at a smaller amount of use, great safety and good selectivity for crops. SOLUTION: A compound or its salt represented by formula (1) (wherein, A is phenyl group, a heterocyclic group, or the like; (n) is an integer of 0-2; R1, R2 and R3 are each hydrogen atom, a 1-6C alkyl group, or the like; X is nitrogen atom, oxygen atom, sulfur atom, or the like; R4 is a 1-6C alkyl group, a 1-6C haloalkyl group, or the like; R5 is hydrogen atom, a 1-6C alkoxycarbonyl group, or the like; R6 is a 1-6C alkyl group, a 3-6C cycloalkyl group, or the like; B is single bond, or the like; and R8 is OR11 or NR14 R15).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to novel 3-aminoacrylic acid derivatives and herbicides.

[0002]

2. Description of the Related Art In cultivating agricultural and horticultural crops, many herbicides have been used for weed control, which has required a great deal of labor. However, since it causes chemical damage to crops, remains in the environment, and contaminates, there is a demand for the development of a drug with a lower dose and which is more effective and can be used safely.

The following compounds are disclosed as compounds related to the compound of the present invention. WO85 / 005
No. 98 describes the herbicidal activity of the compound represented by the general formula [II] and a method for producing the compound.

Embedded image

However, R in the general formula [II]
In the claims, a substituent composed of an alkyl group and a cycloalkyl group, a formula of-(CHRc) m
-Ar [wherein, Ar represents a phenyl group which may be substituted, Rc represents a hydrogen atom, an alkyl group, or a phenylalkyl group having a phenyl group which may be substituted, and m represents 1 to 4 A phenylalkyl group represented by the following formula: or a formula-(CH ₂ ) _p -Het wherein
Het represents a heterocyclic group, and p represents an integer of 1 to 4]. The alkyl group substituted by the heterocyclic group represented by the formula (1) is described, and there is no description of the compound of the present invention. Not enough. The compound most relevant to the present invention is [IIa].

Further, Chemical Journal of Chinese Universities, 1999, Vol. 20, No. 9, pp. 1404-8, describes a method for synthesizing a compound represented by the general formula [III] and herbicidal activity. is there.

Embedded image

However, in this document, R ₄ of the present invention is used.
And the herbicidal activity is not always sufficient. Compounds most relevant to the present invention [III
a] is raised.

[0007]

SUMMARY OF THE INVENTION An object of the present invention is to provide a novel compound which can be advantageously synthesized industrially, and which can be used as a herbicide which is effective at a lower dose, is highly safe, and has good selectivity to crops. Is to provide.

[0008]

The present invention provides a compound represented by the general formula [I]:

Embedded image [In the formula, A represents an optionally substituted phenyl group or an optionally substituted heterocyclic group, and n represents 0 to 2
R ₁ , R ₂ , and R ₃ each independently represent a hydrogen atom, a C _1-6 alkyl group, or a carbonyl group with R ₁ and R ₂ ; ₁ and R ₁ or R ₂ and R ₂ may form a single bond (for example,

Embedded image X) X represents a nitrogen atom, an oxygen atom or a sulfur atom when A represents a phenyl group which may be substituted, or n is 2 and R ₁ and R ₁ or R ₂ and R ₂ form a single bond. When A represents a heterocyclic group which may be substituted, A represents a single bond, a nitrogen atom, an oxygen atom or a sulfur atom, and R ₄ represents a C _1-6 alkyl group, _1-6 haloalkyl group, C _3-6 cycloalkyl group, a phenyl group which may be substituted, C _1-6 alkoxycarbonyl group, -CO
NR ₉ R ₁₀ {wherein R ₉ and R ₁₀ each independently represent a hydrogen atom or a C _1-6 alkyl group}, a C _1-6 alkoxy C _1-6 alkyl group, a C _1-6 alkylthio C R ₅ represents a hydrogen atom, a C _1-6 alkoxycarbonyl group, a C _1-6 alkylcarbamoyl group, a C _1-6 alkyl group or a cyano group;
_{Represents a 1-6} alkoxy C _1-6 alkyl group or a C _1-6 alkylthio C _1-6 alkyl group, wherein R ₆ is a C _1-6 alkyl group, a C _3-6 cycloalkyl group, a C _1-6 haloalkyl Group, C
_{1- 6} alkoxy group, a C _1-6 alkylthio group, or a cyano group, R ₇ is a cyano group, C _1-6 haloalkyl groups, C
_{Represents a 1-6} alkylsulfonyl group or an optionally substituted heterocyclic group, and B represents a carbonyl group or a single bond when R ₇ represents a C _1-6 haloalkyl group or a substituted heterocyclic group; When R ₇ represents a group other than a substituted heterocyclic group, it represents a single bond, R ₈ is OR ₁₁ , wherein R ₁₁ is a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _3-6 cycloalkyl group. Alkyl group, phenyl C _1-6 alkyl group which may be substituted at any position of benzene ring, C _1-6 alkoxy C _1-6 alkyl group, phenyl which may be substituted at any position of benzene ring C _1-6 alkoxy C _1-6 alkyl group, C _1-6 alkylthio C _1-6 alkyl group, mono- or di-C _1-6 alkylamino, di-C _1-6 alkylmethylideneamino, or N
R ₁₂ R ₁₃ (wherein R ₁₂ and R ₁₃ each independently represent a hydrogen atom, a C _1-6 alkyl group, or a C _1-6 alkoxy C _1-6 alkyl group)}, or NR ₁₄ R ₁₅中 where R ₁₄ and R ₁₅
Each independently represents a hydrogen atom, a C _1-6 alkyl group,
_1-6 haloalkyl group, C _3-6 cycloalkyl group, phenyl C _1-6 optionally substituted at any position of the benzene ring
Alkyl group, C _1-6 alkoxy C _1-6 alkyl group, C _1-6
An alkylthio C _1-6 alkyl group, an optionally substituted heterocyclic group, or OR ₁₆ (wherein R ₁₆ is a hydrogen atom,
_1-6 represents an alkyl group) represents〕]
An aminoacrylic acid derivative compound or a salt thereof and a herbicide.

The above A is preferably

Embedded image In the formula, R ₁₇ , R ₁₈ and R ₁₉ each independently represent a hydrogen atom, a C _1-12 alkyl group, a C _1-6 haloalkyl group, a C _1-6 alkoxy group, a C _1-6 alkylthio group, _1-6 alkylsulfonyl group, C _1-6 alkoxycarbonyl group, C _1-6 alkylamino group, di C _1-6 alkylamino group, a halogen atom, a cyano group, a nitro group, a substituent at any position of the benzene ring Or a phenyl group selected from｝ representing a phenoxy group having a substituent at any position of the benzene ring, or a heterocyclic group, wherein R ₁₇ and R ₁₈ , or R ₁₈ and R ₁₉ together To form a condensed ring. ]
Is a type of group selected from the group represented by

In the present invention, C _1-6 alkyl refers to a C _1-6 alkyl.
6 means an alkyl group, for example, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, hexyl group, etc., and particularly preferably has 1 to 3 carbon atoms. Halogen is fluorine, bromine, chlorine or iodine. Preferably fluorine,
Bromine and chlorine. Examples of the C _1-6 haloalkyl group include chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, trichloroethyl, trifluoroethyl, pentafluoroethyl and the like. _1-6 haloalkyl groups are exemplified. The C _1-6 alkoxy group, methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec- butoxy, isobutoxy, include C _1-6 alkoxy group such as t- butoxy. The C _1-6 alkylsulfonyl group, methylsulfonyl, ethylsulfonyl, propylsulfonyl, include C _1-6 alkylsulfonyl groups such as a butylsulfonyl. The C _1-6 alkylcarbamoyl group, methylcarbamoyl, ethylcarbamoyl, propylcarbamoyl, include C _1-6 alkylcarbamoyl group such as butylcarbamoyl. The C _1-6 alkoxycarbonyl group, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, include C _1-6 alkoxycarbonyl group such as a t- butoxycarbonyl. Examples of the heterocyclic group represented by R ₇ include a nitrogen atom such as pyrazinyl, thiazolyl, and pyridyl, and a 5- to 6-membered heterocyclic ring containing 1 to 2 sulfur atoms, which are substituted with C _1-6 alkyl or the like. May be.

Representative examples of the compound of the present invention are shown below. In addition,
The abbreviations in Table 2 represent the meanings in Table 1.

[0012]

[Table 1]

[0013]

[Table 2]

[0014]

[Table 3]

[0015]

[Table 4]

[0016]

[Table 5]

[0017]

[Table 6]

[0018]

[Table 7]

[0019]

[Table 8]

[0020]

[Table 9]

[0021]

[Table 10]

[0022]

[Table 11]

[0023]

[Table 12]

[0024]

[Table 13]

[0025]

[Table 14]

[0026]

[Table 15]

[0027]

[Table 16]

[0028]

[Table 17]

[0029]

[Table 18]

[0030]

[Table 19]

[0031]

[Table 20]

[0032]

[Table 21]

[0033]

[Table 22]

[0034]

[Table 23]

[0035]

[Table 24]

[0036]

[Table 25]

[0037]

BEST MODE FOR CARRYING OUT THE INVENTION The compound of the present invention can be produced by the following method. Manufacturing method (1)

Embedded image [Wherein, R ₅ , R ₆ , R ₇ , R ₈ , and B represent the same meaning as described above, and Z ₁ represents a C _1-6 alkoxy group, a C _1-6 alkylthio group, a halogen atom, any of a benzene ring. A phenoxy group having a substituent at the position, or a phenylthio group,
R ₂₀ is a formula,

Embedded image (Wherein, A, R ₁ , R ₂ , R ₃ , R ₄ , X and n have the same meanings as described above). That is, compound [IV] and amine R ₅ R ₂₀ NH are each 1
It is produced by reacting in a solvent or in a solvent using an excess of each or one of them in a molar amount. R ₅ is a hydrogen atom or an optionally substituted alkyl group,
When R ₆ is other than an alkoxy group or an alkylsulfonyl group, it can be obtained by this method.

Examples of the solvent that can be used in the reaction in a solvent include hydrocarbons such as benzene and toluene, ethers such as THF and diethyl ether, alcohols such as methanol and ethanol, DMF, and DMF.
SO, or a mixed solvent thereof.

The reaction temperature is preferably from room temperature to 200 ° C., particularly preferably from 50 ° C. to 160 ° C.

As the base, aliphatic amines such as triethylamine, organic bases such as pyridine and the like can be used. Manufacturing method (2)

Embedded image[Wherein, R₆, R₇, R₈, R₂₀B represents the same meaning as described above.
I, R_{twenty one}Is C_1-6Represents an alkyl group, and NCQ is
Represents cyanate or isothiocyanate, Z _TwoIs
A halogen atom, an alkoxy group, or an alkylthio group
And R_{twenty one}Z_ThreeIs a halogenated alkyl such as methyl iodide
Or dialkyl sulfate such as dimethyl sulfate
Represents an agent. Or a compound [VI] and a compound [VII] or a compound
Compound [VIII] in 1 mole each or one in excess
Used by reacting in the presence of a base in a solvent
can do.

As the solvent that can be used here,
Examples include hydrocarbons such as benzene and toluene, ethers such as THF and diethyl ether, halogenated hydrocarbons such as methylene chloride, DMF, DMSO, acetonitrile, and mixed solvents thereof.

The reaction temperature is preferably from -78 ° C to the boiling point of the solvent used, particularly preferably from -10 ° C to room temperature.

Examples of the base include aliphatic amines such as triethylamine, organic bases such as pyridine, alkali metal hydroxides such as KOH and NaOH, alkali metal carbonates such as sodium carbonate and potassium carbonate, calcium hydroxide, and magnesium hydroxide. And alkaline earth metal carbonates such as calcium carbonate, sodium hydride, lithium diisopropylamide and the like.

Further, the compound in which R ₆ is an alkoxy group in the compound [I] can also be obtained by reacting a compound in which R ₆ is an alkylthio group with a corresponding alkoxide such as sodium ethoxide. Examples of the solvent used in the reaction with the alkoxide include alcohols corresponding to the alkoxide, hydrocarbons such as benzene and toluene, and TH.
F, ethers such as diethyl ether, DMF and the like.

[0045]

Embedded image[Where A, R₁, R_Two, R_Three, R_Four, R_Five, X and n are as described above.
Has the same meaning, R _{twenty two}Represents a hydrogen atom, an alkyl group, or
Or an alkoxy group;_FourM₁Is an alkyllithium
Or alkyl magnesium halide
Z_Four, Z_FiveRepresents halogen atoms such as chlorine and bromine atoms.
I forgot. ] The above R_FiveR₂₀NH (where R_Five, R₂₀Is the same as above.
(Indicating taste) is available or manufactured according to known methods.
Compound [IX], Compound [X], Compound [X
I] or compound [XII] according to a known method.
Can be manufactured.

The above compound [IV] can be prepared by reacting compound [VI] with carbon disulfide and a corresponding alkylating agent such as alkyl halide or dialkyl sulfate in the presence of a base such as sodium hydride, or compound [VI]. ] In the presence of a carboxylic anhydride in the presence of a corresponding carboxylic acid orthoester.

The above compound [VI] is a compound such as cyanoacetic acid ester or alkanesulfonylacetic acid ester.
Transesterification or amidation reaction between an acetic acid ester substituted with a corresponding substituent and a corresponding alcohol or a corresponding amine, an alcohol corresponding to acetic acid substituted with a corresponding substituent at the 2-position, or General synthetic chemistry such as reaction with a corresponding amine using a dehydrating condensing agent such as DCC, reaction of acetic acid chloride substituted at the 2-position with a corresponding substituent with a corresponding alcohol or a corresponding amine. It can be manufactured by a technique.

The compound [VII] is a compound [XV
I] or a hydrochloride thereof, or a method of reacting an N-sulfinyl derivative which can be produced by reacting a compound [XVI] with thionyl chloride with phosgene or thiophosgene, or a method of reacting a compound [XV] with a cyanic acid such as silver cyanate or potassium thiocyanate. It can be produced by a general synthetic chemical technique such as a method of reacting a salt or a thiocyanate.

The compound [VIII] is a compound [XV
I] and the corresponding amide is produced by an acylating agent such as a carboxylic acid, a carboxylic acid ester, a carboxylic acid chloride or a carboxylic anhydride, and then a halogen such as phosgene, thionyl chloride, phosphorus oxychloride or phosphorus pentachloride. General synthetic chemistry techniques, such as a method of reacting with a reagent, a method of converting the corresponding amide to a thioamide with a sulfurizing agent such as phosphorus pentasulfide or Lawesson's reagent, and then reacting with an alkylating agent such as methyl iodide or dimethyl sulfate. Can be manufactured.

Here, the compound [I] of the present invention has an optical isomer
And geometric isomers, _FiveIs a hydrogen atom
When multiple tautomers, for example B is a single bond,

Embedded image Or, when B is a carbonyl group,

Embedded image May exist in the form of All such forms are within the scope of the present invention. The structure of the compound of the present invention was determined by NMR, IR, MS and the like.

The compounds of the present invention will be described in more detail with reference to the following examples.

Example 1 2-ethoxyethyl 3-{[1- (6-chloro (3-
Pyridyl)) ethyl] amino} -2-cyanopent-2
-Method for producing enoate (Compound No. 25)

Embedded image 1- (6-chloro-3-pyridyl) ethylamine 2.4
4 g and 3.13 g of 2-ethoxyethyl 2-cyano-3-ethoxypent-2-enoate in 6 ml of ethanol
And stirred under reflux for 1 hour. After concentrating the reaction solution, a small amount of ethyl acetate was added, and the precipitate was filtered. The filtrate was purified by column chromatography to obtain 1.30 g of the desired product as a white solid. Melting point 76-78 ° C

Example 2 2-ethoxyethyl 3-{[1- (2-methyl (4-
Thiazolyl)) ethyl] amino} -2-cyanopent-
Method for producing 2-enoate (compound No. 52)

Embedded image 1- (2-methyl-4-thiazolyl) ethylamine
40 g and 0.70 g of 2-ethoxyethyl 2-cyano-3-ethoxypent-2-enoate were mixed,
Stirred at C for 30 minutes. After the reaction mixture was cooled at room temperature, it was purified by column chromatography to obtain the target compound (0.6).
1 g was obtained as a pale yellow oil. Refractive index n _d ^{21 .7} 1.5419

Example 3 3- {2- (4-chlorophenoxy) -1-methylethylamino} -2-cyano-N- (2-methoxyethyl)
-3-methylthioprop-2-enamide (compound number
54) Manufacturing method

Embedded image 0.37 g of 2-amino-1- (4-chlorophenoxy) propane and 2-cyano-N- (2-methoxyethyl)
0.45 g of -3,3-bis (methylthio) prop-2-enamide was dissolved in 5 ml of ethanol, and the mixture was stirred under reflux for 2 hours. The reaction solution was concentrated and purified by column chromatography to obtain 0.70 g of the desired product as a pale yellow oil.
Refractive index n _d ^22.1 1.5855

Example 4 2-ethoxyethyl 3-{[1- (6-chloro (3-
Pyridyl)) ethyl] amino} -2-cyano-4,4,
4-trifluorobut-2-enoate (compound number
29) Manufacturing method

Embedded image 0.79 g of 2-ethoxyethyl cyanoacetate in a suspension of 0.24 g of sodium hydride (oily, about 60% pure) and 5 ml of dry N, N-dimethylformamide
Was added dropwise and stirred at room temperature for 30 minutes. 3-aza-
2-chloro-4- (6-chloro (3-pyridyl))-
1.36 g of 1,1,1-trifluoropent-2-ene
After stirring at room temperature for 24 hours, 10% hydrochloric acid was added, and the mixture was extracted three times with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and concentrated, and then purified by column chromatography to obtain 0.48 g of the desired product as a pale yellow oil. Refractive index n _d ^26.4 1.5079

Representative examples of the compounds of the present invention obtained as described above, including the above Examples, are shown in Tables 3 and 4.

[0056]

[Table 26]

[0057]

[Table 27]

[0058]

[Table 28]

[0059]

[Table 29]

[0060]

[Table 30]

[0061]

[Table 31]

The compound of the present invention (the compound represented by the formula [I] or a salt thereof) shows high herbicidal activity in soil treatment and foliage treatment under upland cultivation conditions, and is useful for various upland weeds such as crabgrass, Achinoekorogosa, Ichibai and Inubiyu. Effective, corn,
It also contains compounds that show selectivity for crops such as wheat, soybeans, and cotton.

The compounds of the present invention also include compounds exhibiting a plant growth regulating effect such as a growth inhibiting effect on useful plants such as crops, ornamental plants and fruit trees.

The compounds of the present invention also include compounds that have excellent herbicidal activity against various paddy weeds such as paddy weeds such as Nobie, Tamayatsuri, Omodaka and Firefly, and show selectivity to rice.

The compounds of the present invention can also be applied to the control of weeds in orchards, lawns, track ends, open spaces and the like.

The compounds of the present invention include those having a plant growth regulating activity, a bactericidal activity, and an insecticidal / miticidal activity. The intermediate compounds of the compounds of the present invention include those having herbicidal activity.

[0067]

[Herbicide] The herbicide of the present invention contains one or more of the compounds of the present invention as an active ingredient. When actually applying the compound of the present invention, it can be used in a pure form without adding other components. Also,
Possible forms of general pesticides for use as pesticides,
That is, they can be used in the form of wettable powders, granules, powders, emulsions, aqueous solvents, suspensions, flowables and the like.

When a solid agent is intended, as an additive and a carrier, a vegetable powder such as soybean flour, flour, or a mineral fine powder such as diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite, clay, etc. , Sodium benzoate, urea,
Organic and inorganic compounds such as sodium sulfate are used.

When a liquid dosage form is intended, petroleum fractions such as kerosene, xylene and solvent naphtha, cyclohexane, cyclohexanone, DMF, DMSO, alcohol, acetone, trichloroethylene, methyl isobutyl ketone, mineral oil, vegetable oil, Use water or the like as a solvent.

Further, in order to obtain a uniform and stable form in these preparations, other additives such as a surfactant may be added as necessary. Examples of the surfactant include, but are not particularly limited to, alkyl phenyl ether to which polyoxyethylene is added, alkyl ether to which polyoxyethylene is added, higher fatty acid ester to which polyoxyethylene is added, and sorbitan to which polyoxyethylene is added. Nonionic surfactants such as higher fatty acid esters, tristyryl phenyl ether added with polyoxyethylene, sulfates of alkyl phenyl ether added with polyoxyethylene, alkyl benzene sulfonates, sulfates of higher alcohols,
Examples thereof include alkyl sulfates, alkyl naphthalene sulfonates, polycarboxylates, lignin sulfonates, formaldehyde condensates of alkyl naphthalene sulfonates, and copolymers of isobutylene-maleic anhydride.

The active ingredient concentration in the herbicide of the present invention can be changed to various concentrations depending on the form of the preparation described above. The active ingredient concentration is, for example, about 5 to 90%, preferably about 10 to 85% in a wettable powder,
The content of the emulsion is about 3 to 70%, preferably about 5 to 60%, and the use of granules is about 0.01 to 50%, preferably about 0.05 to 40%.

The wettable powder and emulsion thus obtained are:
Dilute to a predetermined concentration with water to form a suspension or emulsion,
The granules are directly sprayed or mixed before or after germination of the weeds. In actually applying the herbicidal composition of the present invention as a herbicide, an appropriate amount of 0.1 g or more of the active ingredient per hectare is applied.

The herbicide of the present invention can be used in admixture with known fungicides, insecticides, acaricides, herbicides, plant growth regulators, fertilizers and the like. In particular, it is possible to reduce the amount of the drug used by mixing and using the herbicide. In addition to saving labor, a higher effect can be expected due to the synergistic action of the mixed drug. In that case, a combination with a plurality of known herbicides is also possible.

Suitable agents to be used in combination with the herbicide of the present invention include anilide herbicides such as diflufenican and propanil, chloroacetanilide herbicides such as alachlor and pretilachlor, and 2,4-D, 2,4-D.
Aryloxyalkanoic acid herbicides such as B; aryloxyphenoxyalkanoic acid herbicides such as diclohop-methyl and fenoxaprop-ethyl; arylcarboxylic acid herbicides such as dicamba and pyrithiobac; imidazolinones such as imazaquin and imazethapyr Based herbicides, urea herbicides such as diuron and isoproturon, carbamate herbicides such as chlorprofam and fenmedifam, thiocarbamate herbicides such as thiobencarb and EPTC, dinitroaniline herbicides such as trifluralin and pendimethalin, Diphenyl ether herbicides such as acifluorfen and fomesafen; sulfonylurea herbicides such as bensulfuron-methyl and nicosulfuron; triazinone herbicides such as metribuzin and metamitrone;
Triazine herbicides such as atrazine and cyanazine, triazopyrimidine herbicides such as flumeturum, nitrile herbicides such as bromoxynil and diclobenyl, phosphate herbicides such as glyphosate and glyphosinate, paraquat,
Quaternary ammonium salt-based herbicides such as difenzoquat; cyclic imide-based herbicides such as flumicrolac-pentyl and fluthiacet-methyl;
Examples include ethofumesate, oxadiazon, quinclorac, chromazone, sulcotrione, cinmethylin, dithiopyr, pyrazolate, pyridate, flupoxam, bentazone, benflusate, and cyclohexanedione herbicides such as sethoxydim and tralkoxydim. Additives such as vegetable oils and oil concentrates can also be added to compositions combining these.

[0075]

EXAMPLES [Herbicide] Next, some formulation examples of the herbicide of the present invention are shown. However, the active ingredient compounds, additives and addition ratios can be changed in a wide range without being limited only to this example. It is. Parts in Formulation Examples are parts by weight.

Example 5 Wettable powder 20 parts of the compound of the present invention 20 parts of white carbon 52 parts of diatomaceous earth 52 parts of sodium alkylsulfate 8 parts .

Example 6 Emulsion 20 parts of the compound of the present invention 55 parts of xylene 15 parts of dimethylformamide 10 parts of polyoxyethylene phenyl ether 10 parts of the above were mixed and dissolved to obtain an emulsion having an active ingredient of 20%.

Example 7 Granules 5 parts of the compound of the present invention 40 parts of talc 38 parts of clay 10 parts of bentonite 7 parts of sodium alkyl sulfate 7 parts After uniformly mixing and finely pulverizing the mixture, the diameter was 0.5 to 1.
The granules were granulated to a particle size of 0 mm to obtain granules having an active ingredient of 5%.

[0079]

Next, test examples relating to the effect of the herbicide of the present invention will be shown. The herbicidal effect was investigated according to the following criteria and expressed as a weed kill index.

Survey criteria Weed kill ratio Weed kill index 0% 0 20-29% 240-49% 460-69% 680-89% 8 100% 10 Also, 1, 3, 5, 7, 9 The numerical values indicate intermediate values between 0 and 2, 2 and 4, 4 and 6, 6 and 8, and 8 and 10, respectively.

[0081]

(Equation 1)

Test Example 1 Foliage spraying treatment A 200 cm 2 pot was filled with soil, and seedlings of Meishishiba, Achinonokorogosa, Inubiyu and Ichibai were sown on the surface layer, lightly covered with soil, and grown in a greenhouse. Each weed is 5-2
When the plants grew to a height of 5 cm, a water dilution of the emulsion shown in Example 6 was sprayed on the foliage with a small sprayer so that the active ingredient had a predetermined dose. Three weeks later, phytotoxicity of the crop and herbicidal effects of the weeds were investigated in accordance with the above-mentioned criteria, and the results are shown in Table 5.

[0083]

[Table 32] Test Example 2 Upland Soil Treatment A plastic pot having a surface area of 250 cm ² was filled with upland soil, and seeds of Meechishiba, Achinonokorogosa, Ichibi and Inubiyu were sown as weeds, and the seeds were placed on the soil.
The soil was covered by 5 cm. On the next day, the wettable powder diluent shown in Example 5 was evenly sprayed on the covering soil so that the active ingredient amounted to 100 g per 10 a, and the herbicidal effect was investigated 20 days after the treatment. The results are shown in Table 6.

[0084]

[Table 33]

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) A01N 43/40 101 A01N 43/40 101E 4C063 43/58 43/58 Z 4H006 43/60 43/60 4H0143 / 78 43/78 B 43/84 101 43/84 101 C07C 323/60 C07C 323/60 C07D 213/36 C07D 213/36 213/61 213/61 213/64 213/64 215/12 215/12 237 / 08 237/08 241/12 241/12 277/28 277/28 295/22 295/22 Z 307/14 307/14 333/20 333/20 333/28 333/28 401/12 401/12 417/12 417/12 (72) Inventor Hideaki Omura 345 Takada, Odawara-shi, Kanagawa Japan Soda Co., Ltd.Odawara Research Laboratories (72) Inventor Koichi Kudose 345 Odawara-shi, Kanagawa Prefecture Takada, Japan Soda Co., Ltd. Odawara Research Laboratories (72) Inventor Shigeo Yamada 345 Takada, Odawara-shi, Kanagawa Japan Soda Co., Ltd. Odawara Research Laboratory (72) Inventor Kazunari Kato 345 Takada, Odawara-shi, Kanagawa Prefecture Nippon Soda Co., Ltd.Odawara Research Laboratory F-term (reference) CB10 DA01 DA27 DA52 DB08 DB10 FA01 FA32 4C063 AA01 BB07 CC12 CC29 CC54 CC62 DD10 DD12 DD54 EE03 4H006 AA01 AB04 QN30 4H011 AB01 BA01 BB06 BB08 BB09 BB10 BC01 BC06 BC07 BC18 BC19 BC20 DA02 DA13 DA15 DC03 DC06 DD03

Claims (3)

[Claims] 1. A compound of the general formula [I] [In the formula, A represents an optionally substituted phenyl group or an optionally substituted heterocyclic group, and n represents 0 to 2
R ₁ , R ₂ , and R ₃ each independently represent a hydrogen atom, a C _1-6 alkyl group, or a carbonyl group with R ₁ and R ₂ ; ₁ and R ₁ or R ₂ and R ₂ may form a single bond, and X represents a nitrogen atom, an oxygen atom, a sulfur atom when A represents a phenyl group which may be substituted, or n Is 2 and R ₁
And R ₁ or R ₂ and R ₂ represent a single bond, and when A represents a heterocyclic group which may be substituted, a single bond, a nitrogen atom, an oxygen atom, or a sulfur atom And R ₄
Is a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _3-6 cycloalkyl group, an optionally substituted phenyl group,
_1-6 alkoxycarbonyl group, -CONR ₉ R _10
9 and R ₁₀ each independently represent a hydrogen atom or a C _1-6 alkyl group, a C _1-6 alkoxy C _1-6 alkyl group,
A C _1-6 alkylthio C _1-6 alkyl group or a cyano group, wherein R ₅ is a hydrogen atom, a C _1-6 alkoxycarbonyl group,
C _1-6 alkylcarbamoyl group, C _1-6 alkoxy C _1-6
It represents an alkyl group, or a C _1-6 alkylthio C _1-6 alkyl group, R ₆ is, C _1-6 alkyl, C _3-6 cycloalkyl group, C _1-6 haloalkyl group, C _1-6 alkoxy group , C
_1-6 alkylthio group, or a cyano group, R ₇ represents a cyano group, C _1-6 haloalkyl group, C _1-6 alkylsulfonyl group, or an optionally substituted heterocyclic group, B
Is a carbonyl group or a single bond when R ₇ represents a C _1-6 haloalkyl group or a substituted heterocyclic group, when representing a non-heterocyclic group R ₇ is substituted represents a single bond, R
₈ is OR ₁₁ , wherein R ₁₁ is a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _3-6 cycloalkyl group, or a phenyl C _1- optionally substituted at any position of a benzene ring. ₆ alkyl group, C _1-6 alkoxy C _1-6 alkyl group, phenyl C _1-6 alkoxy C _1-6 alkyl group optionally substituted at any position of the benzene ring, C _1-6 alkylthio C _{1- 6} alkyl groups, mono or di C _1-6 alkylamino, di C _1-6
Alkylmethylideneamino or NR ₁₂ R ₁₃ (wherein R ₁₂ and R ₁₃ each independently represent a hydrogen atom, a C _1-6 alkyl group, or a C _1-6 alkoxy C _1-6 alkyl group) Or NR ₁₄ R _{15 wherein} R ₁₄ and R ₁₅ are each independently a hydrogen atom, a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _3-6 cycloalkyl group, or any of a benzene ring A phenyl C _1-6 alkyl group _optionally substituted,
A C _1-6 alkoxy C _1-6 alkyl group, a C _1-6 alkylthio C _1-6 alkyl group, an optionally substituted heterocyclic group, or OR ₁₆ (where R ₁₆ is a hydrogen atom or C _{1 -6} represents an alkyl group) represents 塩] or a salt thereof. 2. The method according to claim 1, wherein A is In the formula, R ₁₇ , R ₁₈ and R ₁₉ each independently represent a hydrogen atom, a C _1-12 alkyl group, a C _1-6 haloalkyl group, a C _1-6 alkoxy group, a C _1-6 alkylthio group, _1-6 alkylsulfonyl group, C _1-6 alkoxycarbonyl group, C _1-6 alkylamino group, di C _1-6 alkylamino group, a halogen atom, a cyano group, a nitro group, a substituent at any position of the benzene ring Or a phenoxy group having a substituent at any position of the benzene ring. Further, R ₁₇ and R ₁₈ , or R ₁₈ and R ₁₉ may be combined to form a condensed ring.基 is a kind of group selected from the group represented by 、
The 3-aminoacrylic acid derivative compound represented by the general formula [I] according to claim 1, or a salt thereof. 3. A compound of the general formula [I] Wherein R ₁ , R ₂ , R ₃ , R ₄ , R ₆ , R ₇ , R ₈ , X,
A, B, and n have the same meanings as described above, and R ₅ represents a hydrogen atom.] Or a salt thereof as an active ingredient.