JPH07330508A - Herbicidal composition - Google Patents

Abstract

PURPOSE:To obtain a herbicidal composition exhibiting remarkable synergistic effect and capable of providing sufficient herbicidal effect at a low dose and enhancing the safety to crops. CONSTITUTION:This herbicidal composition contains (A) an N-acyl-N- phenyltetrahydrophthalamic acid derivative of formula I (X is a halogen; R<1> is a lower alkyl; R<2> is H or R<1>; R<3> is R<1>; R<4> is a 1-6C alkyl, a cycloalkyl, a lower alkenyl, a lower alkynyl or lower alkoxyalkyl), e.g. N-acetyl-N-(4-chloro-2- fluoro-5-methoxycarbonylmethylthiophenyl)-3,4,5,6-tetrahydrophthalamic acid methyl ester and (B) a phenoxypropionic acid derivative of formula II (R<5> is formula III to formula VI; R<6> is a l-4C alkyl), e.g. 2-[4-(5-trifluoromethyl-2- pyridyloxy)phenoxyl-propionic acid-n-butylester in an amount of 0.001-10 pts.wt., especially 0.01-0.5 pts.wt. based on 1 pts.wt. of the component B.

Description

Detailed Description of the Invention

[0001]

The present invention relates to the general formula [I]

[0002]

[Chemical 4]

(In the formula, X represents a halogen atom, R ¹ represents a lower alkyl group, R ² represents a hydrogen atom or a lower alkyl group, R ³ represents a lower alkyl group, and R ⁴ represents C1.
To C6 alkyl group, cycloalkyl group, lower alkenyl group, lower alkynyl group or lower alkoxyalkyl group. ) At least 1 selected from N-acyl-N-phenyltetrahydrophthalamic acid derivatives represented by
Compounds and general formula [II]

[0004]

[Chemical 5]

(Where R ⁵ is

[0006]

[Chemical 6]

R ⁶ represents an alkyl group of C4 or less. The present invention relates to a herbicidal composition containing as an active ingredient at least one compound selected from the phenoxypropionic acid derivatives represented by

[0008]

2. Description of the Related Art Today, many herbicides are used in cultivated lands and non-agricultural lands, which contributes to improvement of crop productivity and labor saving of weeding work. However, the herbicidal effect on a wide variety of weeds that occur cannot be said to be complete, and there is a demand for the development of new agents having superior herbicidal properties.

[0009]

As a result of various investigations on these points, the present inventors show an excellent herbicidal effect at a low dose as compared with conventional herbicides represented by the general formula [I]. It was found that when a compound (Japanese Patent Application No. 6-4205) is blended with a phenoxypropionic acid derivative represented by the general formula [II], a remarkable synergistic effect and a synergistic effect are exhibited, and an excellent herbicidal effect is obtained. Was completed.

That is, the present invention has the general formula [I]

[0011]

[Chemical 7]

(In the formula, X represents a halogen atom, R ¹ represents a lower alkyl group, R ² represents a hydrogen atom or a lower alkyl group, R ³ represents a lower alkyl group, and R ⁴ represents C1.
To C6 alkyl group, cycloalkyl group, lower alkenyl group, lower alkynyl group or lower alkoxyalkyl group. ) At least 1 selected from N-acyl-N-phenyltetrahydrophthalamic acid derivatives represented by
Compounds and general formula [II]

[0013]

[Chemical 8]

(Wherein R ⁵ is

[0015]

[Chemical 9]

R ⁶ represents a C4 or lower alkyl group. And at least one compound selected from the phenoxypropionic acid derivatives represented by the formula (1), as an active ingredient.

The N-acyl-N-phenyltetrahydrophthalamic acid derivative represented by the general formula [I] which is one component of the herbicidal composition of the present invention is a compound developed by the present inventors (Japanese Patent Application No. It is a compound useful as a herbicide that can be widely applied to agricultural land, non-agricultural land, etc. alone.

Specific examples of the N-acyl-N-phenyltetrahydrophthalamic acid derivative represented by the general formula [I] in the herbicidal composition of the present invention include, for example, N-
Acetyl-N- (4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl) -3,4,5,6
-Tetrahydrophthalamic acid methyl ester, N-acetyl-N- (4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl) -3,4,5,6-tetrahydrophthalamic acid ethyl ester, N-acetyl- N- (4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl) -3,4,5,6-tetrahydrophthalamic acid-n-propyl ester, N-acetyl-N- (4-chloro-2- Fluoro-5-methoxycarbonylmethylthiophenyl) -3,4,5,6-tetrahydrophthalamic acid-n-butyl ester, N-propionyl-N- (4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl) -3,4,5,
6-Tetrahydrophthalamic acid methyl ester, N-propionyl-N- (4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl) -3,4,5,5
6-Tetrahydrophthalamic acid ethyl ester, N-propionyl-N- (4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl) -3,4,5,5
6-Tetrahydrophthalamic acid-n-propyl ester, N-propionyl-N- (4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl)-
3,4,5,6-Tetrahydrophthalamic acid-n-butyl ester, N-acetyl-N- [4-chloro-2-fluoro-5- (1-methoxycarbonylethylthio) phenyl] -3,4 5,6-Tetrahydrophthalamic acid methyl ester, N-acetyl-N- [4-chloro-2
-Fluoro-5- (1-methoxycarbonylethylthio) phenyl] -3,4,5,6-tetrahydrophthalamic acid ethyl ester, N-acetyl-N- [4-chloro-2-fluoro-5- (1 -Methoxycarbonylethylthio) phenyl] -3,4,5,6-tetrahydrophthalamic acid-n-propyl ester, N-acetyl-N
-[4-Chloro-2-fluoro-5- (1-methoxycarbonylethylthio) phenyl] -3,4,5,6-tetrahydrophthalamic acid-n-butyl ester, N-propionyl-N- [4- Chloro-2-fluoro-5-
(1-Methoxycarbonylethylthio) phenyl]-
3,4,5,6-Tetrahydrophthalamic acid methyl ester, N-propionyl-N- [4-chloro-2-fluoro-5- (1-methoxycarbonylethylthio) phenyl] -3,4,5,6 -Tetrahydrophthalamic acid ethyl ester, N-propionyl-N- [4-chloro-
2-Fluoro-5- (1-methoxycarbonylethylthio) phenyl] -3,4,5,6-tetrahydrophthalamic acid-n-propyl ester, N-propionyl-N
-[4-Chloro-2-fluoro-5- (1-methoxycarbonylethylthio) phenyl] -3,4,5,6-tetrahydrophthalamic acid-n-butyl ester, N-acetyl-N- (4- Chloro-2-fluoro-5-ethoxycarbonylmethylthiophenyl) -3,4,5,6-
Tetrahydrophthalamic acid methyl ester, N-acetyl-N- (4-chloro-2-fluoro-5-ethoxycarbonylmethylthiophenyl) -3,4,5,6-tetrahydrophthalamic acid ethyl ester, N-acetyl-
N- (4-chloro-2-fluoro-5-ethoxycarbonylmethylthiophenyl) -3,4,5,6-tetrahydrophthalamic acid-n-propyl ester, N-acetyl-N- (4-chloro-2- Fluoro-5-ethoxycarbonylmethylthiophenyl) -3,4,5,6-tetrahydrophthalamic acid-n-butyl ester, N-propionyl-N- (4-chloro-2-fluoro-5-ethoxycarbonylmethylthiophenyl) -3,4,5,6
-Tetrahydrophthalamic acid methyl ester, N-propionyl-N- (4-chloro-2-fluoro-5-ethoxycarbonylmethylthiophenyl) -3,4,5,6
-Tetrahydrophthalamic acid ethyl ester, N-propionyl-N- (4-chloro-2-fluoro-5-ethoxycarbonylmethylthiophenyl) -3,4,5,6
-Tetrahydrophthalamic acid-n-propyl ester,
N-propionyl-N- (4-chloro-2-fluoro-
5-ethoxycarbonylmethylthiophenyl) -3,
4,5,6-Tetrahydrophthalamic acid-n-butyl ester, N-acetyl-N- [4-chloro-2-fluoro-5- (1-ethoxycarbonylethylthio) phenyl] -3,4,5,5 6-Tetrahydrophthalamic acid methyl ester, N-acetyl-N- [4-chloro-2-fluoro-5- (1-ethoxycarbonylethylthio) phenyl] -3,4,5,6-tetrahydrophthalamic acid ethyl ester Ester, N-acetyl-N- [4-chloro-2
-Fluoro-5- (1-ethoxycarbonylethylthio) phenyl] -3,4,5,6-tetrahydrophthalamic acid-n-propyl ester, N-acetyl-N-
[4-chloro-2-fluoro-5- (1-ethoxycarbonylethylthio) phenyl] -3,4,5,6-tetrahydrophthalamic acid-n-butyl ester, N-propionyl-N- [4-chloro -2-Fluoro-5- (1
-Ethoxycarbonylethylthio) phenyl] -3,
4,5,6-Tetrahydrophthalamic acid methyl ester, N-propionyl-N- [4-chloro-2-fluoro-5- (1-ethoxycarbonylethylthio) phenyl] -3,4,5,6-tetrahydro Phthalamic acid ethyl ester, N-propionyl-N- [4-chloro-2
-Fluoro-5- (1-ethoxycarbonylethylthio) phenyl] -3,4,5,6-tetrahydrophthalamic acid-n-propyl ester, N-propionyl-N
Examples thereof include-[4-chloro-2-fluoro-5- (1-ethoxycarbonylethylthio) phenyl] -3,4,5,6-tetrahydrophthalamic acid-n-butyl ester. Table 1 shows particularly representative ones.

[0019]

[Table 1]

The above-exemplified compounds are included in the compound represented by the general formula [I], but the compound represented by the general formula [I] is not limited thereto. In addition, the phenoxypropionic acid derivative represented by the general formula [II], which is the other component of the herbicidal composition of the present invention, is a short review of harbicide and PGRS, edited by Hodogaya Chemical Co., Ltd., 1991 edition,
P. 16-P. 22 is a conventionally known herbicide.

In the herbicidal composition of the present invention, the general formula [I
Specific examples of the phenoxypropionic acid derivative represented by [I] include 2- [4- (5-trifluoromethyl-2-pyridyloxy) phenoxy] propionic acid methyl ester and 2- [4- (5- Trifluoromethyl-
2-Pyridyloxy) phenoxy] propionic acid ethyl ester, 2- [4- (5-trifluoromethyl-2-
Pyridyloxy) phenoxy] propionic acid-n-propyl ester, 2- [4- (5-trifluoromethyl-
2-Pyridyloxy) phenoxy] propionic acid-n-
Butyl ester, 2- [4- (3-chloro-5-trifluoromethyl-2-pyridyloxy) phenoxy] propionic acid methyl ester, 2- [4- (3-chloro-5)
-Trifluoromethyl-2-pyridyloxy) phenoxy] propionic acid ethyl ester, 2- [4- (3-chloro-5-trifluoromethyl-2-pyridyloxy)
Phenoxy] propionic acid-n-propyl ester, 2
-[4- (3-chloro-5-trifluoromethyl-2-
Pyridyloxy) phenoxy] propionic acid-n-butyl ester, 2- [4- (6-chloro-2-benzoxazolyloxy) phenoxy] propionic acid methyl ester, 2- [4- (6-chloro-2- Benzoxazolyloxy) phenoxy] propionic acid ethyl ester,
2- [4- (6-chloro-2-benzoxazolyloxy) phenoxy] propionic acid-n-propyl ester, 2- [4- (6-chloro-2-benzoxazolyloxy) phenoxy] propionic acid -N-butyl ester, 2- [4- (6-chloro-2-quinoxalinyloxy) phenoxy] propionic acid methyl ester, 2-
[4- (6-chloro-2-quinoxalinyloxy) phenoxy] propionic acid ethyl ester, 2- [4- (6
-Chloro-2-quinoxalinyloxy) phenoxy] propionic acid-n-propyl ester, 2- [4- (6-
Examples include chloro-2-quinoxalinyloxy) phenoxy] propionic acid-n-butyl ester, and among these, 2- [4-
(5-Trifluoromethyl-2-pyridyloxy) phenoxy] propionic acid-n-butyl ester (hereinafter,
"Fluazifop-butyl"), 2- [4- (3
-Chloro-5-trifluoromethyl-2-pyridyloxy) phenoxy] propionic acid methyl ester (hereinafter,
"Haloxyfop-methyl"), 2- [4- (6
-Chloro-2-benzoxazolyloxy) phenoxy] propionic acid ethyl ester (hereinafter referred to as "phenoxaprop-ethyl") and 2- [4- (6-chloro-2-quinoxalinyloxy) phenoxy ] The structural formulas of propionic acid ethyl ester (hereinafter referred to as "quizalofop-ethyl") are shown below.

Fluazifop-butyl

[0023]

[Chemical 10]

Haloxyfop-methyl

[0025]

[Chemical 11]

Phenoxaprop-ethyl

[0027]

[Chemical 12]

Quizalofop-ethyl

[0029]

[Chemical 13]

The herbicidal composition of the present invention contains at least one compound selected from the N-acyl-N-phenyltetrahydrophthalamic acid derivatives represented by the above general formula [I] and the above general formula [II]. It can be obtained by blending at least one compound selected from the phenoxypropionic acid derivatives represented by

This compounding effect is large, and for example, even a low concentration at which each single agent constituting the herbicidal composition of the present invention cannot sufficiently exert its effect is sufficient for many weeds. Shows herbicidal effect. Not only can this reduce the amount of drug used, but it also increases the safety of crops, especially soybeans.

The weeds which can be controlled by the herbicidal composition of the present invention include velvetleaf, white-tailed scabbard, blue-billed millet, purslane, ragweed, southern fir, morning glory, American morning glory and other morning glory, American hemlock hemlock, American stag deer, and periwinkle. Such as broad-leaved plants such as, and leaf edible weeds such as Elephantia chinensis, Crabgrass, Steller's grass, Steller's grass, Insectidae sorghum, and cedar, and Cyperaceae weeds such as Kogomegayasuri, Hamarisu.

The mixing ratio of each component of the herbicidal composition according to the present invention depends on the relative activity of each component, but it is generally 1 part by weight of the phenoxypropionic acid derivative represented by the general formula [II]. On the other hand, the compound represented by the general formula [I] was treated with 0.
It is preferably 001 parts by weight to 10 parts by weight, preferably 0.005 parts by weight to 1 part by weight, and more preferably 0.01 parts by weight to 0.5 parts by weight. If the amount is out of this range, the synergistic effect and the synergistic effect of the blended components cannot be sufficiently obtained, and only the same degree of efficacy as when using each single agent constituting the herbicidal composition of the present invention alone is exhibited. However, it is not preferable because the effects such as the reduction of the dose of the above-mentioned drug used and the increase of the safety for crops cannot be sufficiently obtained.

Further, the amount of the herbicidal composition of the present invention to be applied depends on a number of factors, for example, the type of target plant, the growth stage, the application method, the application purpose, the application time, the occurrence of weeds and the like. However, it is generally 1 g as an active ingredient.
An amount of up to 1000 g / ha is suitable, preferably 10
g-500 g / ha, more preferably 100 g-400
g / ha. If it is less than this range, it is not preferable because a sufficient herbicidal effect cannot be obtained. Moreover, even if it is applied more than this range, the herbicidal effect does not change so much, it is only economically disadvantageous,
It may cause problems such as phytotoxicity, residual herbicide in soil, and outflow of herbicide to river.

The herbicidal composition according to the present invention is usually prepared in any dosage form such as granules, wettable powders, suspensions and emulsions by using a carrier, a surfactant and other auxiliary agents as active ingredients. And apply.

As the carrier, kaolin clay, attapulgite clay, bentonite, acid clay clay pyroflight,
Talc, diatomaceous earth, calcite, walnut powder, solid carriers such as ammonium urea sulfate, xylene, aromatic hydrocarbons such as methylnaphthalene, isopropanol, alcohols such as ethylene glycol, acetone cyclohexane, ketones such as isophorone, soybean oil, Examples thereof include vegetable oils such as cottonseed oil, liquid carriers such as dimethyl sulfoxide, N, N-dimethylformamide, acetonitrile and water.

Surfactants used for emulsification, dispersion, etc. include alkyl sulfate ester salts, alkyl sulfonates, alkyl aryl sulfonates, dialkyl sulfosuccinates and esters, polyoxyethylene alkyl aryl ether phosphate ester salts. And anionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene polyoxypropylene block copolymers, and nonionic surfactants such as sorbitan fatty acid esters.

Other auxiliary agents include lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, carboxymethyl cellulose, isopropyl acid phosphate and the like.

The amount of the compound represented by the general formula [I] and the phenoxypropionic acid derivative represented by the general formula [II] contained as active ingredients in the preparation depends on the dosage form at the time of application. Different, but usually 1% to 90% by weight
%, Preferably 2% to 80%, more preferably 5% to
80%. If the content of the active ingredient is less than this range, sufficient herbicidal effect may not be obtained, or
In order to obtain a sufficient herbicidal effect, a large amount of chemicals must be applied, which is economically disadvantageous, which is not preferable. Further, if the content of the active ingredient is more than this range, the content of additives such as carriers, surfactants and other auxiliaries in the formulation becomes insufficient, resulting in granules, wettable powders, suspensions. When it is formulated into a preparation, an emulsion, etc., the characteristics of each dosage form may not be sufficiently imparted, which is not preferable.

[0040]

EXAMPLES Next, formulation examples of the herbicidal composition of the present invention will be shown.
The compounds represented by the general formula [I] are represented by the compound numbers in Table 1, and parts are parts by weight.

Formulation Example 1 Compound No. 1 10 parts Fluazifop-butyl 30 parts Sodium salt of higher alcohol sulfate ester 3 parts Kaolin clay 57 parts Each of these components is uniformly mixed and ground to obtain a wettable powder.

Formulation Example 2 Compound No. 2 4 parts Quizalofop-ethyl 20 parts Polyoxyethylene alkylaryl ether 10 parts Cyclohexanone 30 parts N, N-Dimethylformamide 36 parts These components are uniformly dissolved to obtain an emulsion.

Formulation Example 3 Compound No. 3 4 parts Haloxyfop-methyl 30 parts Polyoxyethylene alkylaryl ether 10 parts Cyclohexanone 30 parts N, N-Dimethylformamide 26 parts These components are uniformly dissolved to obtain an emulsion.

Formulation Example 4 Compound No. 4 2 parts Phenoxaprop-ethyl 30 parts Polyoxyethylene alkylaryl ether 10 parts Cyclohexanone 30 parts N, N-Dimethylformamide 28 parts These components are uniformly dissolved to obtain an emulsion. .

Formulation Example 5 Compound No. 5 5 parts Fluazifop-Butyl 5 parts Polyoxyethylene sorbitan monooleate 2 parts Carboxymethyl cellulose 2 parts Water 86 parts These components are mixed and wet pulverized to obtain a suspension having a particle size of 5 microns or less. Make a suspension.

The herbicidal composition of the present invention is prepared by diluting the above-mentioned preparation to an appropriate concentration and then spraying it or directly applying it. Further, it is also effective to add an auxiliary agent such as the above-mentioned surfactant or polyoxyethylene resin acid (ester) or petroleum oil, if necessary.

Next, examples will be shown in order to specifically describe the herbicidal composition of the present invention. Example 1 A 15 cm diameter plastic pot was filled with upland soil,
Seed of sorghum or sorghum was sown. After covering the soil to a depth of 1 cm and growing it in a greenhouse, an emulsion prepared according to Formulation Example 2 when the test plant was in the 3 to 4 leaf stage was applied to the foliage with a small sprayer at a water amount of 10 liters per are. It was spray treated. On the 21st day after the treatment, the herbicidal effect was investigated according to the evaluation criteria shown in Table 2 below. The results are shown in Table 3, Table 4, Table 5 and Table 6.

[0048]

[Table 2]

[0049]

[Table 3]

[0050]

[Table 4]

[0051]

[Table 5]

[0052]

[Table 6]

Example 2 A plastic pot having a diameter of 20 cm was filled with field soil,
Seeds of soybean, velvetleaf, black fir and morning glory were sown. The soil was covered to a depth of 1 cm and grown outdoors. Thereafter, the emulsion prepared according to Formulation Example 2 was spray-treated on the foliage with a small sprayer at a water amount of 10 liters per are when the test plant was in the 1 to 4 leaf stage. After processing, 21
The herbicidal effect was investigated on the day. The results are shown in Table 7 and Table 8.
Shown in.

[0054]

[Table 7]

[0055]

[Table 8]

[0056]

EFFECTS OF THE INVENTION The herbicidal composition of the present invention has a sufficient herbicidal effect against many weeds even at such a low concentration that each single drug constituting the herb cannot exert its effect sufficiently. Show. Not only can this reduce the amount of drug used, but it also increases crop safety.

Front page continuation (72) Inventor Takeo Furumata 2805 Imafuku Nakadai, Kawagoe City, Saitama Central Research Institute of Tokyo (72) Inventor Yukio Ikeda 2805 Imafukuchudai, Kawagoe City, Saitama Central Glass Co., Ltd. In the laboratory (72) Yumiko Kanda 2805 Imafuku Nakadai, Kawagoe City, Saitama Central Glass Co., Ltd.

Claims (3)

[Claims] 1. A compound represented by the general formula [I]: (In the formula, X represents a halogen atom, R ¹ represents a lower alkyl group, R ² represents a hydrogen atom or a lower alkyl group, R ³ represents a lower alkyl group, and R ⁴ represents a C1 to C6 alkyl group. , A cycloalkyl group, a lower alkenyl group, a lower alkynyl group or a lower alkoxyalkyl group), and at least one compound selected from the N-acyl-N-phenyltetrahydrophthalamic acid derivatives and the general formula [II]. [Chemical 2] (In the formula, R ⁵ is And R ⁶ represents an alkyl group of C4 or less. ) At least one compound selected from the phenoxypropionic acid derivatives represented by the formula (1) is contained as an active ingredient. 2. An N-acyl-N-phenyltetrahydrophthalamic acid derivative is N-acetyl-N- (4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl) -3,4,5,6-tetrahydro. Phthalamic acid methyl ester, N-acetyl-N- (4-chloro-2
-Fluoro-5-methoxycarbonylmethylthiophenyl) -3,4,5,6-tetrahydrophthalamic acid-n
-Butyl ester, N-propionyl-N- (4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl) -3,4,5,6-tetrahydrophthalamic acid methyl ester, N-acetyl-N- [4 -Chloro-
2-Fluoro-5- (1-methoxycarbonylethylthio) phenyl] -3,4,5,6-tetrahydrophthalamic acid methyl ester, N-acetyl-N- (4-chloro-2-fluoro-5-ethoxy The herbicidal composition according to claim 1, which is at least one compound selected from carbonylmethylthiophenyl) -3,4,5,6-tetrahydrophthalamic acid-n-butyl ester. 3. The phenoxypropionic acid derivative is 2-
[4- (5-trifluoromethyl-2-pyridyloxy) phenoxy] propionic acid-n-butyl ester,
2- [4- (3-chloro-5-trifluoromethyl-2)
-Pyridyloxy) phenoxy] propionic acid methyl ester, 2- [4- (6-chloro-2-benzoxazolyloxy) phenoxy] propionic acid ethyl ester, 2- [4- (6-chloro-2-quinoxa) The herbicidal composition according to claim 1 or 2, which is at least one compound selected from linyloxy) phenoxy] propionic acid ethyl ester.