JPH054976A - Triazole derivative, its production and herbicide - Google Patents

Abstract

PURPOSE:To provide the subject new compound having selectivity to crops, exhibiting herbicidal activity to harmful weeds in paddy field and plowed land at a low rate of application and useful as a herbicide. CONSTITUTION:The compound of formula I [A is (substituted) alkyl, (substituted) aryl, etc.; X is O or S; R<1> is 1-6C alkyl, 3-6C alkenyl, 1-6C alkoxy, etc.; R<2> is 1-6C alkyl or 3-6C alkenyl; R<1> and R<2> may together form a ring of formula II (Y is single bond, 0, S, etc.; E<1> to E<4> are H or 1-6C alkyl; p and q are 0-4) ; R<3> is H or 1-6C alkyl; n is 0-2], e.g. 3-(p-methylphenoxysulfonyl)-1,2,4-triazole. The compound of formula I can be produced by reacting a substituted triazole of formula III with a carbamoyl halide of formula IV (Hal is halogen).

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel triazole derivative and a selective herbicide containing the derivative as an active ingredient.

[0002]

2. Description of the Related Art Conventionally, a wide variety of chemicals have been put into practical use through many years of research and development of herbicides, and these herbicides have contributed to labor saving of weed control work and improvement of productivity of agricultural and horticultural crops. It was Even today, there is a demand for the development of a new drug having more excellent herbicidal properties, and as a herbicide for agriculture and horticulture, it is possible to control only target weeds selectively and at a low dose without affecting the cultivated crops. However, existing agents do not always have suitable herbicidal properties. On the other hand, it is known that certain compounds such as N-carbamoyltriazole compounds have herbicidal activity, for example, West German Patent No. 2132618.
No. 4,280,831, JP-A-59-398.
No. 80 and Japanese Patent Application Laid-Open No. 2-1481.

However, the conventional N-carbamoyltriazole compounds have weak points such that a large amount of a drug is required to exert a sufficient herbicidal effect and that they are not sufficiently safe for crops. Therefore, there is a strong demand for a drug having a low dose and high safety for crops.

[0004]

The present invention provides the formula (1):

[0005]

[Chemical 12]

[Wherein A is an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted aryl group, Represents an optionally substituted aromatic heterocycle or an optionally substituted aralkyl group, X represents an oxygen atom or a sulfur atom, and R ¹ represents ^{1 to 1} carbon atoms.
A C6 alkyl group, a C3-6 alkenyl group, a C3-6 alkynyl group, or a C1-6
R ² represents an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 3 to 6 carbon atoms or an alkynyl group having 3 to 6 carbon atoms, and R ¹ and R ² represent

[0007]

[Chemical 13]

A ring represented by the following formula may be formed (provided that Y is
Represents a single bond, an oxygen atom, a sulfur atom or N—E ⁵ ,
E ¹ , E ² , E ³ , E ⁴ and E ⁵ each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and p
And q each independently represent an integer of 0 to 4. ), R
³ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and n represents an integer of 0 to 2. ] The triazole derivative represented by the following (hereinafter referred to as the compound of the present invention), a method for producing the same, and a herbicide containing one or more of them.

The compound of the present invention has excellent selectivity for crops such as rice, corn, soybean, wheat, barley, sorghum, and cotton, and has a low dose and is excellent for highly damaging weeds in paddy fields and fields. Shows herbicidal activity. Conventionally, N
Various studies have been conducted on carbamoyltriazole derivatives, but no compound having a substituent such as the compound of the present invention at the 3-position of triazole has been known.

As a result of repeated studies in search of excellent herbicides, the present inventors have found a method for easily producing an N-carbamoyltriazole derivative which has hitherto been unknown and an excellent herbicidal activity thereof. The invention was completed. Examples of the substituents A, R ¹ , R ² , R ³ and X of the compound of the present invention include the following. However, the compound of the present invention is not limited to this.

A: Methyl, ethyl, n-propyl, i-
Propyl, n-butyl, i-butyl, s-butyl, t-
An alkyl group such as butyl, n-amyl, s-amyl, t-amyl and n-hexyl. Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,6-dimethylcyclohexyl, 2,2,6,
Cycloalkyl groups such as 6-tetramethylcyclohexyl, 2,6-di-s-butylcyclohexyl and cycloheptyl.

Alkenyl groups such as vinyl, allyl, 2-butenyl, 3-butenyl, 4-butenyl, isopropenyl, geranyl and citronellyl, and alkynyl groups such as propargyl. Phenyl, 2-pyridyl, 3-pyridyl, 4-
Pyridyl, 2-thienyl, 3-thienyl, 2-furyl,
3-furyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl, 5-
Imidazolyl, 3- (1,2,4-triazolyl), 5-
(1,2,4-triazolyl), 2-pyrimidyl, 4-pyrimidyl, 5-pyrimidyl, 3-pyridazyl, 4-pyridazyl, 2-pyrazyl, s-triazyl, 3- (1,2,4-
Triazyl), 5- (1,2,4-triazyl), 6- (1,
2,4-triazyl), 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 2- (1,3,4-thiadiazolyl), 3- (1,2, 4-thiadiazolyl), 5-
(1,2,4-thiadiazolyl), 5- (1,2,3-thiadiazolyl), 2-oxazolyl, 4-oxazolyl, 5-
Oxazolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 2- (1,3,4-oxadiazolyl), 3- (1,2,4-oxadiazolyl), 5
An aryl group or heterocyclic group such as-(1,2,4-oxadiazolyl), 5- (1,2,3-oxadiazolyl), 1-naphthyl, 2-naphthyl.

Benzyl, α-methylbenzyl, α-ethylbenzyl, α-n-propylbenzyl, α-isopropylbenzyl, α-n-butylbenzyl, cumyl, α,
Examples thereof include aralkyl groups such as α-diethylbenzyl. Further, as a substituent for these alkyl group, cycloalkyl group, alkenyl group, and alkynyl group, a halogen atom (fluorine, chlorine, bromine, iodine), an alkoxy group (methoxy, ethoxy, n-propoxy, i-propoxy, t-butoxy). Etc.), cyano group, alkoxycarbonyl group (methoxycarbonyl, ethoxycarbonyl,
n-propoxycarbonyl, i-propoxycarbonyl, t-butoxycarbonyl, etc.), alkylcarbonyloxy group (acetyloxy, propionyloxy, etc.), alkylcarbonylamino group (acetylamino,
Propionylamino etc.), dialkylamino group (dimethylamino, diethylamino, di-n-propylamino, di-i-propylamino etc.), alkylcarbonyl group (acetyl, propionyl, n-propylcarbonyl, i-propylcarbonyl, t- Butylcarbonyl), and nitro groups.

As a substituent for the aryl group, heterocyclic group and aralkyl group, a halogen atom (fluorine, chlorine, bromine, iodine), an alkoxy group (methoxy, ethoxy, n).
-Propoxy, i-propoxy, t-butoxy, etc.),
Cyano group, alkenyloxy group (allyloxy, 2-butenyloxy, 3-butenyloxy, 4-butenyloxy, etc.), alkynyloxy group (propargyloxy, etc.), alkoxycarbonyl group (methoxycarbonyl,
Ethoxycarbonyl, n-propoxycarbonyl, i-
Propoxycarbonyl, t-butoxycarbonyl, etc.), alkylcarbonyloxy groups (acetyloxy,
Propionyloxy, etc.), alkylcarbonylamino groups (acetylamino, propionylamino, etc.), dialkylamino groups (dimethylamino, diethylamino, di-n-propylamino, di-i-propylamino, etc.), alkylcarbonyl groups (acetyl, propionyl, etc.) , N-propylcarbonyl, i-propylcarbonyl, t-butylcarbonyl, etc.), nitro group, alkyl group (methyl, ethyl, n-propyl, i-propyl, n
-Butyl, i-butyl, s-butyl, t-butyl, etc.), halogenated alkyl groups (trifluoromethyl, trichloromethyl, etc.), halogenated alkyloxy groups (trifluoromethoxy, difluoromethoxy, etc.), halogenated alkylthio Group (trifluoromethylthio, difluoromethylthio, etc.), halogenated alkylsulfonyl group (trifluoromethylsulfonyl, etc.), alkylthio group (methylmercapto, ethylmercapto, n-propylmercapto, etc.), alkylsulfonyl group (methanesulfonyl, ethanesulfonyl) Etc.), alkoxyalkyl groups (methoxymethyl, ethoxymethyl, etc.), alkenyl groups (allyl, 2-butenyl, 3-butenyl, 4-butenyl, isopropenyl, etc.), halogenated alkenyl groups (2-chloroallyl, 3-). Roruariru, 2,3 - Jikuroruariru, 3,3 - Jikuroruariru, such as 2,3,3-trichloro-allyl), an alkynyl group (propargyl), benzoyl group, phenyl group, phenoxy group.

R ¹ : methyl, ethyl, n-propyl, i
-Propyl, n-butyl, i-butyl, s-butyl, t
-Butyl, n-amyl, i-amyl, s-amyl, t-
Amyl, n-hexyl, allyl, 2-butenyl, 3-butenyl, 4-butenyl, propargyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy,
Examples include n-amyloxy and n-hexyloxy.

R ² : methyl, ethyl, n-propyl, i
-Propyl, n-butyl, i-butyl, s-butyl, t
-Butyl, n-amyl, i-amyl, s-amyl, t-
Amyl, n-hexyl, allyl, 2-butenyl, 3-butenyl, 4-butenyl, propargyl and the like can be mentioned. Furthermore, as an example of forming a ring with R ¹ and R ² ,

[0017]

[Chemical 14]

And the like. R ^3: a hydrogen atom, methyl, ethyl, n- propyl, i- propyl, n- butyl, i- butyl, s- butyl, t- butyl, n- amyl, i- amyl, s- amyl, t-amyl, n-hexyl etc. are mentioned. X: An oxygen atom and a sulfur atom are mentioned.

The compound of the present invention can be easily produced by the following synthetic method.

[0020]

[Chemical 15]

[In the formula, A, R ¹ , R ² , R ³ , X and n have the same meanings as described above, and Hal represents a halogen atom. ] The reaction represented by (1) is usually 0.9 to 9 in the presence of a solvent.
It is carried out in the presence of 2.0 equivalents of base. Any solvent may be used as long as it is inert to the reaction, and the following may be mentioned as an example.

Halogenated hydrocarbons such as chloroform, methylene chloride, carbon tetrachloride, dichloroethane and trichloroethane, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene, ethers such as diethyl ether and tetrahydrofuran, Acetone, ketones such as methyl ethyl ketone, pyridine,
Organic bases such as triethylamine, N, N-dimethylaniline, esters such as ethyl acetate and methyl acetate,
In addition to acetonitrile, N, N-dimethylformamide, dimethylsulfoxide, water and the like, alcohol as a reaction material may be used in excess also as a solvent.

Examples of the base include inorganic salts such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate and sodium hydride, as well as pyridine, triethylamine, N, N-dimethylaniline, N, N-diethylaniline, 4-N, N-
Organic salts such as dimethylpyridine can also be used. The reaction temperature may be from -50 ° C to 200 ° C, but is preferably from the freezing point to the boiling point of the solvent in operation.

The reaction time depends on the reaction conditions, but is usually completed in 5 minutes to 100 hours. The reaction represented by (2) is usually 0.9 to
It is carried out in the presence of 2.0 equivalents of base. Any solvent may be used as long as it is inert to the reaction, and the following may be mentioned as an example. Chloroform, methylene chloride, carbon tetrachloride, dichloroethane,
Halogenated hydrocarbons such as trichloroethane, aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene, ethers such as diethyl ether and tetrahydrofuran, acetone, ketones such as methyl ethyl ketone, pyridine, triethylamine, N , N
-Organic bases such as dimethylaniline, ethyl acetate, esters such as methyl acetate, acetonitrile, N, N-
Examples thereof include dimethylformamide, dimethylsulfoxide, and water.

Examples of the base include inorganic salts such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate and sodium hydride, as well as pyridine, triethylamine, N, N-dimethylaniline, N, N-diethylaniline, 4-N, N-
Organic salts such as dimethylpyridine can also be used. The reaction temperature may be from -50 ° C to 200 ° C, but is preferably from the freezing point to the boiling point of the solvent in operation.

The reaction time depends on the reaction conditions, but is usually completed in 5 minutes to 100 hours. After the completion of the reaction, a usual post-treatment is carried out, and if necessary, it can be purified by recrystallization, column chromatography or the like. The compound represented by (1) can also be obtained by continuously performing the reaction of (1) and the reaction of (2) without isolating the compound represented by (2).

[0027]

[Example 1]

3- (p-methylphenoxysulfonyl) -1,2,4
-Preparation of triazole (invention compound 1-4) 0.65 g of p-cresol was added to 30 ml of benzene, 1.0 g of triethylamine and 3-chlorosulfonyl-
1.0 g of 1,2,4-triazole was added sequentially. 1 at room temperature
After stirring for an hour, the reaction solution was heated to 60 ° C. and the stirring was continued for another hour. After completion of the reaction, the solvent was distilled off from the reaction solution under reduced pressure, 50 ml of water was added, and then 1.0 ml of concentrated hydrochloric acid was added.
After further adding 100 ml of ethyl acetate, the ethyl acetate layer was separated. 50 ml of ethyl acetate layer and 50 ml of saturated saline solution
After washing successively with ml, the extract was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure to obtain 1.35 g of the title object compound. Melting point 152-153 ° C By the same method as in Example 1, the following compound was obtained.

Table 1

[0029]

[Chemical 16]

─────────────────────────── Compound AR ³ n Melting point number (℃) ──────── ─────────────────── 1--1 Ph H 2 129-130 1- 2 2-Me-Ph H 2 154-155 1- 3 3-Me-Ph H 2 131-132 1- 4 4-Me-Ph H 2 152-153 1- 5 2,6-Me ₂ -Ph H 2 179-182 1- 6 2-CH ₂ CH = CH ₂ -Ph H 2 85- 86 1- 7 2,6-Cl ₂ -Ph H 2 203-205 ───────────────────────────

Table 1 (continued) ─────────────────────────── Compound AR ³ n Melting point number (℃) ── ───────────────────────── 1- 8 2,4,6-Me ₃ -Ph H 2 155-158 1- 9 2-NO ₂ -4-Me-Ph H 2 123-124 1-10 2-CN-Ph H 2 109-110 1-11 2,3,6-Me ₃ -Ph H 2 180-181 1-12 2-OEt-Ph H 2 134-136 1-13 3-NMe ₂ -Ph H 2 115-119 1-14 2-Ph-Ph H 2 198-200 1-15 2,4,6-Cl ₃ -Ph H 2 170-172 1-16 1-Naphthyl H 2 162-166 1-17 2-Naphthyl H 2 72- 75 1-18 2-Et-Ph H 2 101-103 1-19 2,6-F ₂ -Ph H 2 131- 133 1-20 4-PhO-Ph H 2 173-174 1-21 4-Ac-Ph H 2 147-150 1-22 4-NO ₂ -Ph H 2 178-179 1-23 3-NO ₂ -Ph H 2 135-137 1-24 2-NO ₂ -Ph H 2 187-188 1-25 2-CO ₂ Me-Ph H 2 108-110 1-26 4-CF ₃ -Ph H 2 145-148 1- 27 2-Ac-Ph H 2 122-124 1-28 2-MeO-Ph H 2 123-125 1-29 3-MeO-Ph H 2 137-139 ────────────── ──────────────

Table 1 (continued) ─────────────────────────── Compound AR ³ n Melting point number (° C) ── ───────────────────────── 1-30 4-MeO-Ph H 2 130-133 1-31 4-MeS-Ph H 2 135- 136 1-32 1-Me-4-CO ₂ Et- H 2 134-135 Pyrazole-5-yl 1-33 1-Me-4-CO ₂ Et- H 2 204-205 Pyrazole-3-yl 1-34 4,6-Me ₂ -H 2 150-153 Pyrimidin-2-yl 1-35 2-Me- H 2 110-115 Pyridine-5-yl 1-36 3-CO ₂ Me-Ph H 2 120-125 1 -37 4-CO ₂ Me-Ph H 2 88- 89 1-38 3-CF ₃ -Ph H 2 116-120 1-39 2-Cl- H 2 193-195 Pyridine-3-yl 1-40 3- Ac-Ph H 2 83- 87 1-41 Ph Me 2 142-145 ───────────────────────────

Example 2 Preparation of 1- (diethylcarbamoyl) -3-phenoxysulfonyl-1,2,4-triazole (inventive compound 2-1) 3-phenoxysulfonyl-1,2,4-triazole (compound no. 1-1) 0.8 g was dissolved in 50 ml of acetonitrile, 0.8 g of anhydrous sodium carbonate and 0.6 g of N, N-diethylcarbamoyl chloride were sequentially added, and then the mixture was heated and stirred under reflux of the solvent for 2 hours. After the reaction was completed, the solvent was distilled off under reduced pressure, 100 ml each of chloroform and water was added, and the mixture was stirred well and the chloroform layer was separated. Chloroform layer is water 1
This was washed successively with 00 ml and 50 ml of saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to give a crude product of the title object compound. The crude product was subjected to silica gel column chromatography (eluent n-hexane-ethyl acetate).
Was purified to obtain 0.95 g of the title object compound. Melting point 51-52 ° C. By the same method as in Example 2, the following compound of the present invention was obtained. Table 2

[0034]

[Chemical 17]

─────────────────────────────── Compound A n X R ¹ R ² R ³ Melting point number (℃ ) ─────────────────────────────── 2- 1 Ph 2 O Et Et H 51- 52 2- 2 2-Me -Ph 2 O Et Et H 57- 58 2- 3 3-Me-Ph 2 O Et Et H 105-106 2- 4 4-Me-Ph 2 O Et Et H 84- 86 2- 5 2,6-Me ₂ -Ph 2 O Et Et H 82- 83 2- 6 2-CH ₂ CH = CH ₂ -Ph 2 O Et Et H 68- 69 2- 7 2,6-Cl ₂ -Ph 2 O Et Et H 76- 78 2- 8 2,6-Cl ₂ -Ph 2 S Me Me H 96- 99 2- 9 2,4,6-Me ₃ -Ph 2 O Et Et H 94- 96 2-10 2,4,6- Me ₃ -Ph 2 O-(CH ₂ ) ₂ O (CH ₂ ) ₂ -H 105-110 2-11 2,4,6-Me ₃ -Ph 2 O Me Me H 69- 72 2-12 2-t -Bu-Ph 2 O Et Et H oily 2-13 2-NO ₂ -4-Me-Ph 2 O Et Et H 103-106 2-14 2-CN-Ph 2 O Et Et H oily 2-15 2, 3,6-Me ₃ -Ph 2 O Et Et H 82- 85 2-16 2-OEt-Ph 2 O Et Et H 114-116 2-17 2-NO ₂ -4-Me-Ph 2 O-(CH ₂ ) ₂ O (CH ₂ ) ₂ -H oily 2-18 3-NMe ₂ -Ph 2 O Et Et H 55- 58 2-19 2-Ph-Ph 2 O Et Et H 118-120 2-20 2, 4,6-Cl ₃ -Ph 2 O Et Et H 98-101 2-21 2,4,6-Me ₃ -Ph 2 O i-Pr i-Pr H 140-142 ────────── ──────────────────────

Table 2 (continued) ─────────────────────────────── Compound An X R ¹ R ² R ³ Melting point number (℃) ─────────────────────────────── 2-22 3-pyridyl 2 O Et Et H 60 -62 2-23 1- Naphthyl 2 O Et Et H 69- 72 2-24 2-Naphthyl 2 O Et Et H 72- 75 2-25 2-Et-Ph 2 O Et Et H 74- 76 2-26 2 , 6-F ₂ -Ph 2 O Et Et H 92- 95 2-27 4-Pyridyl 2 O Et Et H Oily 2-28 2-Pyridyl 2 O Et Et H 78- 81 2-29 4-PhO-Ph 2 O Et Et H Oily 2-30 4-Ac-Ph 2 O Et Et H 77- 79 2-31 4-NO ₂ -Ph 2 O Et Et H 104-105 2-32 3-NO ₂ -Ph 2 O Et Et H 58- 60 2-33 2-NO ₂ -Ph 2 O Et Et H oily 2-34 2-CO ₂ Me-Ph 2 O Et Et H 63- 65 2-35 4-CF ₃ -Ph 2 O Et Et H 60- 63 2-36 2-Ac-Ph 2 O Et Et H oily 2-37 2-MeO-Ph 2 O Et Et H 82- 85 2-38 3-MeO-Ph 2 O Et Et H 74- 77 2-39 4-MeO-Ph 2 O Et Et H 65- 68 2-40 4-MeS-Ph 2 O Et Et H 80-83 2-41 4-MeSO ₂ -Ph 2 O Et Et H 15 8-161 ────────────────────────────────

Table 2 (continued) ─────────────────────────────── Compound An X R ¹ R ² R ³ Melting point number (℃) ─────────────────────────────── 2-42 1-Me-4-CO ₂ Et - 2 O Et Et H oil pyrazol-5-yl 2-43 1-Me-4-CO 2 Et- 2 O Et Et H 121-124 pyrazol-3-yl 2-44 4,6-Me ₂ - ₂ O Et Et H 105-108 Pyrimidin-2-yl 2-45 2-Me- 2 O Et Et H 95- 97 Pyridine-5-yl 2-46 3-CO ₂ Me-Ph 2 O Et Et H 68- 69 2 -47 4-CO ₂ Me-Ph 2 O Et Et H 113-115 2-48 3-CF ₃ -Ph 2 O Et Et H 78-79 2-49 2-Cl- 2 O Et Et H 53- 55 Pyridine -3-yl 2-50 2-Me- 2 O Et Et H 71- 74 pyridine-6-yl 2-51 3-Ac-Ph 2 O Et Et H oily 2-52 Ph 2 O Et Et Me oily 2- 53 2-Pyridyl 2 O Et Et Me 66- 68 ───────────────────────────────

The compounds synthesized according to the above Examples are shown in Tables 3 and 4 including the above Examples. However, the present invention is not limited to these. In the table, A represents the following structural formula, and A means that the position designated by the substituent b is substituted.

[0039]

[Chemical 18]

[0040]

[Chemical 19]

[0041]

[Chemical 20]

Table 3

[0043]

[Chemical 21]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[Chemical formula 22]

[0088]

[0089]

[0090]

[0091]

Table 4 (continued)

[0093]

[0094]

[0095]

[0096] When the compound of the present invention is used as a herbicide for agricultural and horticultural use, it is generally a suitable carrier, for example, a solid carrier such as clay, talc, bentonite, diatomaceous earth or water, alcohols (methanol, ethanol, etc.), aromatic hydrocarbons. (Benzene, toluene, xylene, etc.), chlorinated hydrocarbons, ethers, ketones, esters (ethyl acetate, etc.), acid amides (dimethylformamide, etc.) If desired, add emulsifiers, dispersants, suspensions, penetrants, spreading agents, stabilizers, etc. and put them into practical use in any dosage form such as liquids, emulsions, wettable powders, powders, granules and flowables. Can be offered. Further, if necessary, it may be mixed and applied with other kinds of herbicides, various insecticides, fungicides, plant growth regulators, synergists, etc. during preparation or spraying. The types of herbicides to be mixed are, for example, Farm Chemicals Handbook (Farm ChemicalsHa
ndbook) compounds described in the 1989 edition. Some of them are atrazine, cyanadine, alachlor metolachlor, EPTC, 2,4
-D, butyrate, dicamba, bromoxynil, tridifane and the like. The applied dose varies depending on the application scene, application time, application method, cultivated crop, etc., but is generally 0.00 per hectare as the active ingredient amount.
About 1 to 10 kg is suitable.

Next, formulation examples of the herbicide containing the compound of the present invention as an active ingredient are shown, but the invention is not limited thereto. In the following formulation examples, "part" means part by weight. [Formulation Example 1] Wettable powder Compound No. 2-1 of the present invention 2-1 ──────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────── Trade name) Solpol 5039 ─────────── 5 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical Industry Co., Ltd. trade name) Carplex (anti-caking Agent) ───── 2 parts (White carbon: Shionogi Pharmaceutical Co., Ltd. trade name) The above is uniformly mixed and pulverized to obtain a wettable powder.

[Formulation Example 2] Emulsion Compound No. 2-7 of the present invention ─────── 1.5 parts xylene ────────────── 78.5 parts N, N- Dimethylformamide ───── 15 parts Sorbol 2680 ─────────── 5 parts (mixture of nonionic surfactant and anionic surfactant: trade name of Toho Chemical Industry Co., Ltd.) The above is uniformly mixed to obtain an emulsion.

[Formulation Example 3] Flowable agent Compound No. 2-1 of the present invention 2-1 --- 40 parts Agrisol B-710 ──────── 10 parts (Nonionic surfactant: Kao Corporation trade name) Lunox 1000C ─────────── 0.5 part (Anionic surfactant: trade name of Toho Chemical Industry Co., Ltd.) 1% Rhodopol water ────────── 20 parts (Thickener: Loan Boulan's product name) Water ───────────────── 29.5 parts The above is uniformly mixed to obtain a flowable agent.

[Formulation Example 4] Granule Compound No. 2-4 of the present invention ────── 1 part Bentonite ────── 55 parts Tar ─────── 44 parts After that, a small amount of water is added, and the mixture is kneaded with stirring, kneaded, granulated by an extrusion granulator, and dried to give granules.

The compound of the present invention can be used for controlling various weeds in non-agricultural fields such as athletic fields, open spaces and route ends, as well as agricultural and horticultural fields such as upland fields, paddy fields and orchards. Although there are differences depending on the application scene, application time, target grass species, etc., generally 0.001 to 5 per hectare
It is suitable to sprinkle it to about kg. Next, the herbicidal effect of the compound of the present invention will be specifically described with reference to test examples.

[Test Example-1] Herbicidal effect test under flooded condition After alluvial soil was put into a 1/5000 ares Wagner pot, water was added to mix it to obtain a flooded condition of 4 cm depth. Seeds of millet, firefly, eel, and yellow grass were mixed-sown in the above pot, and rice seedlings at the 2.5 leaf stage were further transplanted.
Put the pots in a greenhouse at 25-30 ° C to grow and sow 3
After a day, the drug diluted solution was dropped onto the water surface with a measuring pipette so that a predetermined amount of the drug was applied. Three weeks after the treatment, the herbicidal effect on rice and various weeds was investigated according to the following criteria. The results are shown in Table 5.

Criteria 5: Complete death or suppression of 90% or more 4: 70-90% suppression 3: 40-70% suppression 2: 20-40% suppression 1: 5-20% suppression 0: Suppression of 5% or less The degree of suppression was determined by visual observation.

The symbols in the table represent the following. A: hie, B: firefly, C: eel, D: yellow grass, a: transplanted rice

[0105]

[Test Example-2] Herbicidal effect test by soil treatment The diluvial soil was put in a plastic box having a length of 30 cm, a width of 30 cm, and a depth of 10 cm, and then, the millet, the crabgrass, the green locust, the shatter cane, the corn, the soybean, and the cotton were used. After mixed seeding and covering with about 1.5 cm of soil, the surface of the soil was uniformly treated with the chemical diluting solution so as to have a predetermined amount. 4 weeks after treatment,
The herbicidal effect was investigated according to the criteria shown in Test Example-1. The results are shown in Table 6.

The symbols in the table represent the following. A: millet, E: crabgrass, F: green foxtail, G: shatter cane, b: corn, c: soybean, d: cotton

[0108]

Continuation of the front page (51) Int.Cl. ⁵ Identification number Reference number within the agency FI Technical display area C07D 409/12 249 8829-4C 413/12 249 8829-4C 417/12 249 9051-4C (72) Inventor Watanabe Shigenomi 1470 Shiraoka, Shirooka-cho, Minami-Saitama-gun, Saitama Prefecture, Institute of Biological Sciences, Nissan Kagaku Kogyo Co., Ltd. (72) Inventor Toshiharu Endo, 1470, Shiraoka, Shiraoka-cho, Minami-Saitama-gun, Saitama Prefecture, Institute of Biological Sciences, Nissan Kagaku Kogyo Co., Ltd.

Claims (6)

[Claims] 1. Formula (1): [Wherein A is an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted aryl group, or a substituted Represents an aromatic heterocyclic group or an optionally substituted aralkyl group, X represents an oxygen atom or a sulfur atom, R ¹ represents an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 3 to 6 carbon atoms. , 3 to 3 carbon atoms
6 represents an alkynyl group having 6 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms, R ² represents an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 3 to 6 carbon atoms or an alkynyl group having 3 to 6 carbon atoms. Where R ¹ and R ² are In represented by may form a ring (where, Y represents a single bond, an oxygen atom, a sulfur atom or ^{N-E 5, E 1,} E 2,
E ³ , E ⁴ and E ⁵ each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and p and q each independently represent an integer of 0 to 4. ) And R ^{3 each} represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and n represents an integer of 0 to 2. ] The triazole derivative represented by these. 2. Formula (1 ′): [In the formula, A'is an alkyl group having 1 to 12 carbon atoms which may be substituted by a (a is a halogen atom, an alkoxy group having 1 to 6 carbon atoms, an alkoxycarbonyl group having 2 to 6 carbon atoms, An alkylcarbonyloxy group having 2 to 6 carbon atoms, an alkylcarbonylamino group having 2 to 6 carbon atoms, an amino group substituted by 1 to 2 by the same or different alkyl group having 1 to 6 carbon atoms, and 2 carbon atoms ~ 6 alkylcarbonyl group, cyano group or nitro group), a cycloalkyl group having 3 to 8 carbon atoms optionally substituted by a (a represents the same meaning as described above), substituted by a. Number of carbon atoms that may be 2 to 1
2 alkenyl groups (a has the same meaning as above),
an alkynyl group having 2 to 12 carbon atoms which may be substituted by a (a represents the same meaning as described above), an aryl group which may be substituted by b (the aryl group represents a phenyl group or a naphthyl group, b is an alkyl group having 1 to 6 carbon atoms, a halogenoalkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a halogenoalkenyl group having 2 to 6 carbon atoms, and 2 to 6 carbon atoms. Alkynyl group, phenyl group, halogen atom, alkoxy group having 1 to 6 carbon atoms, halogenoalkoxy group having 1 to 6 carbon atoms, alkenyloxy group having 2 to 6 carbon atoms, alkynyl having 2 to 6 carbon atoms Oxy group, phenoxy group, alkylthio group having 1 to 6 carbon atoms, halogenoalkylthio group having 1 to 6 carbon atoms, alkylsulfonyl group having 1 to 6 carbon atoms, number of carbon atoms 6 halogenoalkyl alkylsulfonyl group, an alkoxyalkyl group having from 2 to 8 carbon atoms, an alkoxycarbonyl group having 2 to 6 carbon atoms, alkylcarbonyloxy group having 2 to 6 carbon atoms, 2 carbon atoms
6 alkylcarbonylamino group, an amino group substituted by 1 to 2 by the same or different alkyl group having 1 to 6 carbon atoms, alkylcarbonyl group having 2 to 6 carbon atoms, benzoyl group, cyano group or nitro group . ), An aromatic heterocyclic group which may be substituted by b (the aromatic heterocyclic group is a thienyl group, a furyl group, a pyrazolyl group, an imidazolyl group, a 1,2,4-triazolyl group, a thiazolyl group, an isothiazolyl group, 1, 3,4-thiadiazolyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, pyridyl group, pyrimidyl group, pyridazyl group, pyrazyl group, S-triazyl group or 1,2,4
Represents a triazyl group, and b represents the same as above. Or an aralkyl group in which a phenyl group may be substituted by b (an aralkyl group represents an alkyl group having 1 to 6 carbon atoms, which is substituted by a phenyl group, and b represents the same as described above), and X represents X. Represents an oxygen atom or a sulfur atom, R
¹ is an alkyl group having 1 to 6 carbon atoms, 3 to 6 carbon atoms
Represents an alkenyl group having 3 to 6 carbon atoms, or an alkynyl group having 3 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms, and R ² represents an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 3 to 6 carbon atoms, or carbon. Represents an alkynyl group having 3 to 6 atoms,
R ¹ and R ² are In represented by may form a ring (where, Y represents a single bond, an oxygen atom, a sulfur atom or ^{N-E 5, E 1,} E 2,
E ³ , E ⁴ and E ⁵ each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, p and q each independently represent an integer of 0 to 4, and R ³ represents a hydrogen atom or It represents an alkyl group having 1 to 6 carbon atoms, and n represents an integer of 0 to 2. ] The triazole derivative of Claim 1 represented by these. 3. A herbicide containing one or more triazole derivatives according to claim 1 as an active ingredient. 4. Formula (2): [Wherein A is an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted aryl group, or a substituted Represents an aromatic heterocyclic group or an optionally substituted aralkyl group, R ³ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and n represents an integer of 0 to 2. ] The substituted triazole represented by these. 5. Formula (2): [Wherein A is an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted aryl group, or a substituted Represents an aromatic heterocyclic group or an optionally substituted aralkyl group, R ³ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and n represents an integer of 0 to 2. ] To the substituted triazole represented by the formula (3): [In the formula, X represents an oxygen atom or a sulfur atom, R ¹ is an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 3 to 6 carbon atoms, an alkynyl group having 3 to 6 carbon atoms, or the number of carbon atoms. 1 to 6 represents an alkoxy group, R ² represents an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 3 to 6 carbon atoms or an alkynyl group having 3 to 6 carbon atoms, and R ¹ and R ² are [Chemical 8] In represented by may form a ring (where, Y represents a single bond, an oxygen atom, a sulfur atom or ^{N-E 5, E 1,} E 2,
E ³ , E ⁴ and E ⁵ each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and p and q each independently represent an integer of 0 to 4. ) And n represent the integer of 0 to 2, and Hal represents a halogen atom. ] A carbamoyl halide represented by the following formula (1) characterized by reacting: [In the formula, A, n, R ¹ , R ² , R ³ and X have the same meanings as described above. ] The manufacturing method of the triazole derivative represented by these. 6. Formula (4): A—OH (4) [wherein A is an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkenyl group, or a substituted Represents an optionally substituted alkynyl group, an optionally substituted aryl group, an optionally substituted aromatic heterocyclic group or an optionally substituted aralkyl group. ] To the compound represented by the formula (5): [In the formula, Hal represents a halogen atom, R ³ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and n represents an integer of 0 to 2. ] The formula (2) characterized by reacting the triazole represented by: [In the formula, A, R ³ and n have the same meanings as described above. ] The manufacturing method of the substituted triazole represented by these.