JPH0776504A - Herbicidal composition - Google Patents

Abstract

PURPOSE:To obtain a herbicidal composition exhibiting high synergistic effect and exhibiting high herbicidal effect at a low dose and simultaneously having broad weeding spectrum and high safety to crops. CONSTITUTION:This herbicidal composition is obtained by blending (A) a triazine derivative of formula I {A is formula II [Z is O or S], formula III [X<2> is methyl or F; (n) is 0-2]; R<1> is H or methyl; X<1> is F or Cl}, e.g. 2- amino-4-[1-(benzofuran-2'-yl)ethylamino]-6-(alpha-fluoro, alpha-methylethyl)-S-triazine with (B) a chloroacetoamide-based herbicide selected from 2-chloro-2',6'-diethyl- N-methoxymethylacetoanilide of formula IV, 2-chloro-2'-ethyl-N-(2-methoxy-1- methylethyl)-6'-methylacetoanilide of formula V and 2-chloro-N- isopropylacetoanilide of formula VI in a weight ratio of the component A: the component B of (10:1) to (1:50).

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a herbicide composition containing a triazine derivative and a specific chloroacetamide herbicide as active ingredients.

[0002]

BACKGROUND OF THE INVENTION Various herbicides have been developed so far and have contributed to agricultural productivity and labor saving. However, since some herbicides have been used for many years, the number of difficult-to-control weeds to which these herbicides are ineffective is increasing, and the herbicidal spectrum is wide and effective against these difficult-to-control weeds. The appearance of agents is desired. Further, in order to solve the problem of environmental pollution caused by conventional herbicides, development of highly active herbicides has been desired. Furthermore, in order to cope with the uneven development of weeds over a long period of time, it has excellent residual efficacy and is effective even after being treated over a wide range of time from the emergence of weeds to the growing season. The appearance of drugs is also awaited.

Under these circumstances, the present inventors have found that the triazine derivative having a specific novel haloalkyl has no phytotoxicity on the Gramineae field crop, and does not control weeds in soil or foliar treatment. It has already been found that the compound has a high herbicidal effect and an excellent waterlogging soil treatment effect (International Publication No. WO 90/09378).
International patent application published in). The present inventors have conducted extensive studies to further improve the herbicidal activity of the triazine derivative.

[0004]

As a result, a composition in which the triazine derivative and a specific chloroacetamide herbicide are combined has a high synergistic effect which cannot be expected from the properties of each of them alone, and a low dose is required. The present invention was completed based on this finding, showing that it exhibits an excellent herbicidal effect with a wide herbicidal spectrum and is highly safe for crops.

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

[Chemical 7] [In the formula, A is the following formula (a)

[Chemical 8] (However, Z represents an oxygen atom or a sulfur atom.) Or Formula (b)

[Chemical 9] (However, X ² represents a methyl group or a fluorine atom, n represents an integer of 0 to 2), R ¹ represents a hydrogen atom or a methyl group, and X ¹ represents a fluorine atom or a chlorine atom. ] A triazine derivative represented by the formula [II]-

[Chemical 10] A compound represented by the following formula [II]-

[Chemical 11] And a compound represented by the following formula [II]-

[Chemical 12] The present invention provides a herbicidal composition containing, as an active ingredient, one of chloroacetamide herbicides selected from the group consisting of compounds represented by:

The herbicidal composition of the present invention comprises a triazine derivative represented by the above general formula [I] and the above formula [II].
-A compound represented by-, a compound represented by the above formula [II]-and one of the chloroacetamide herbicides selected from the group consisting of the compound represented by the above formula [II]-as an active ingredient Is.

Specific examples of the triazine derivative represented by the above general formula [I] are as follows. First,
formula

[Chemical 13] 2-amino-4- [1- (benzofuran-
2'-yl) ethylamino] -6- (α-fluoro, α
-Methylethyl) -s-triazine.

Next, the formula

[Chemical 14] 2-amino-4- [1- (benzofuran-
2'-yl) ethylamino] -6- (α-fluoroethyl) -s-triazine.

Further, the formula

[Chemical 15] 2-amino-4- [1- (benzothiophen-2′-yl) ethylamino] -6- (α-fluoro, α-methylethyl) -s-triazine represented by

Further, the formula

[Chemical 16] 2-amino-4- (α-fluoro, α-methylethyl) -6- [2- (3 ′, 5′-dimethylphenoxy) -1-methyl-ethylamino] -s-triazine represented by .

Then, the formula

[Chemical 17] 2-amino-4- (α-fluoro, α-methylethyl) -6- [2- (3′-fluorophenoxy) -1-methyl-ethylamino] -s-triazine represented by

Further, the formula

[Chemical 18] 2-amino-4- (α-chloro, α-methylethyl) -6- [2- (3 ′, 5′-dimethylphenoxy) -1-methylethylamino] -s-triazine represented by

Further, the equation

[Chemical 19] 2-amino-4- (α-fluoro, α-methylethyl) -6- [2- (3 ′, 5′-dimethylphenoxy) -1-methyl-ethylamino] -s-triazine represented by be able to.

The triazine derivative represented by the above general formula [I] can be produced by various methods. Among them, an efficient production method is disclosed in International Publication No. WO 90/09378. There are methods described in international patent applications. Details are left to this publication.

The herbicidal composition of the present invention comprises a triazine derivative represented by the above general formula [I] and the above formula [I].
I]-, a compound represented by the above formula [II]-, and a compound represented by the above formula [II]-, and one of the chloroacetamide herbicides selected from the group consisting of: To do. The compound represented by the above formula [II]-is 2-chloro-2 ',
It is 6'-diethyl-N-methoxymethylacetanilide, and its generic name is alachlor. Next, the compound represented by the above formula [II]-is 2-chloro-2′-ethyl-N- (2-methoxy-1-methylethyl) -6′-methylacetanilide, and its general name is metolachlor. Is called. Further, the compound represented by the above formula [II]-is 2-chloro-N-isopropylacetanilide, whose generic name is propacrole. These formulas [II]-, [I
The compounds represented by [I]-and [II]-are all chloroacetamide-based herbicides and can be obtained by known methods.

Compounds belonging to these chloroacetamide herbicides are used as grass weed control agents in grass crops such as corn and sorghum, or broad-leaved crops such as soybean and cotton. Is insufficient for broad-leaved weeds such as.

The herbicidal composition of the present invention comprises a triazine derivative represented by the above general formula [I] and the above formula [II].
A chloroacetamide herbicide selected from the group consisting of a compound represented by-, a compound represented by the above formula [II]-and a compound represented by the above formula [II]-(hereinafter, a specific chloroacetamide herbicide , Which is sometimes referred to as an active ingredient,
The mixing ratio is not particularly limited, and an excellent synergistic effect can be obtained in a wide mixing ratio. Usually, it is preferable to mix the triazine derivative: chloroacetamide herbicide within the range of 10: 1 to 1: 500 (weight ratio).

In the herbicidal composition of the present invention, the triazine derivative represented by the general formula [I] and a specific chloroacetamide herbicide are mixed with a liquid carrier such as a solvent or a solid carrier such as a mineral powder. However, it can be used by formulating it in the form of wettable powder, emulsion, powder, granule, flowable agent, liquid agent and the like. Upon formulation, a surfactant such as an emulsifier, a dispersant, a spreading agent, a suspending agent, a penetrating agent, a stabilizer, and other auxiliary agents may be added, if desired.

When the herbicidal composition of the present invention is used in the form of a wettable powder, it is usually 10 to 55% by weight of a mixture of the above-mentioned triazine derivative and a specific chloroacetamide herbicide as an active ingredient and a solid carrier. The composition may be prepared by blending 40 to 88% by weight and a surfactant in a proportion of 2 to 5% by weight, and this may be used. When used in the form of an emulsion and a flowable agent, usually 5 to 50% by weight of a mixture of the above-mentioned triazine derivative and a specific chloroacetamide herbicide as an active ingredient, a solvent (liquid carrier) 3
It may be prepared by blending 5 to 90% by weight, and a surfactant and other auxiliary agents in a proportion of 5 to 15% by weight.

On the other hand, when it is used in the form of a powder, the mixture of the above-mentioned triazine derivative and a specific chloroacetamide herbicide as an active ingredient is usually contained in an amount of 1 to 15% by weight and a solid carrier in an amount of 85 to 99% by weight. It may be prepared by mixing in a ratio. Furthermore, when used in the form of granules, 0.1 to 15% by weight of a mixture of the above-mentioned triazine derivative and a specific chloroacetamide herbicide as an active ingredient,
85 to 97.9 wt% solid carrier and 2 to surfactant
It may be prepared by blending at a ratio of 5% by weight.

Here, a fine powder of a mineral substance is used as the solid carrier, and examples of the fine powder of a mineral substance include oxides such as diatomaceous earth and slaked lime, phosphates such as apatite, and sulfates such as gypsum. , Talc, pyroferrite, clay, kaolin, bentonite, acid clay, white carbon,
Examples thereof include silicates such as quartz powder and silica stone powder.

As the liquid carrier, kerosene, mineral oil,
Paraffinic or naphthenic hydrocarbons such as spindle oil, aromatic hydrocarbons such as benzene, toluene, xylene, chlorinated hydrocarbons such as o-chlorotoluene, trichloromethane, trichloroethylene, cyclohexanol,
Amyl alcohol, alcohol such as ethylene glycol, alcohol ether such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ketone such as isophorone, cyclohexanone, cyclohexenyl-cyclohexanone, ether such as butyl cellosolve, dimethyl ether, methyl ethyl ether,
Examples thereof include esters such as isopropyl acetate, benzyl acetate and methyl phthalate, amides such as dimethylformamide, nitriles such as acetonitrile and propionitrile, sulfoxides such as dimethylsulfoxide, organic solvents such as mixtures thereof, water and the like.

Further, as the surfactant, anionic type (alkylbenzene sulfonate, alkyl sulfonate, lauric acid amide sulfonate, etc.), nonionic type (polyoxyethylene octyl ether, polyethylene glycol laurate, sorbitan alkyl ester) are used. Etc.), cationic type (dimethyllaurylbenzylammonium chloride, laurylamine, stearyltrimethylammonium chloride, etc.) or zwitterionic type (amino acid, betaine, etc.) can be used.

In addition, the herbicidal composition of the present invention contains a polymeric compound such as sodium alginate, carboxymethylcellulose, carboxyvinyl polymer, arabic gum, hydroxypropylmethylcellulose or the like, for the purpose of improving the properties of the preparation and enhancing the herbicidal effect. Agents can also be used in combination.

Such a herbicidal composition of the present invention has excellent effects as a highly selective herbicide with no phytotoxicity, by treating soil for field crops such as corn and sorghum before germination of weeds. Demonstrate. Further, it has a high herbicidal effect not only on annual weeds but also on perennial weeds, and is extremely useful as a highly selective herbicide which is not harmful to lawns.

Further, the herbicidal composition of the present invention is applied to soil treatment or foliage treatment of weeds in orchards or non-agricultural land (factory area, railway site, roadside, riverside site, fallow land). Therefore, it exerts an excellent control effect.

The herbicidal composition of the present invention is applied with about 1 to 10,000 g, preferably 10 to 1,000 g, per 10 ares of the active ingredient. Also, 10 to 100,00 when sprayed on plant foliage
It is diluted to about 0 ppm, preferably 100 to 10,000 ppm and applied.

The herbicidal composition of the present invention can be used in combination with other herbicidal ingredients. Examples of herbicidal components that can be used here include diphenyl ether-based, triazine-based, phenoxyacetic acid-based, carbamate-based, thiocarbamate-based, acid anilide-based, pyrazole-based, phosphoric acid-based, and imidazolinone that are commercially available herbicides. System, dinitroaniline system, sulfonylurea system, bromoxynil, ioxynil, oxadiazone and the like. Furthermore, the herbicidal composition of the present invention can be mixed with insecticides, fungicides, plant growth regulators, fertilizers, etc., if necessary.

[0029]

EXAMPLES The present invention will now be described with reference to examples. First, the formulation method will be specifically described with reference to formulation examples. In addition, "part" in the following formulation examples means% by weight. As the triazine derivative (Compound A), the compounds shown in Table 1 (Compound Nos. A-1 to A-7) were used, and as the chloroacetamide herbicide (Compound B), the compounds shown in Table 2 (Compounds) were used. No. B-1 to B-3) were used.

[0030]

[Table 1]

[0031]

[Table 2]

[0032]

[Table 3]

Formulation Example 1 [Wettable powder] Compound No. A-1 5 parts Compound No. B-1 15 parts Diatomaceous earth 62 parts White carbon 15 parts Sodium alkylbenzene sulfonate 2 parts Sodium lignin sulfonate 1 part The above components were mixed and uniformly pulverized to obtain 100 parts of a wettable powder.

Formulation Example 2 [Emulsion] Compound No. A-2 10 parts Compound No. B-2 30 parts Xylene 20 parts Dimethylformamide 20 parts Solpol 2806B 20 parts (Toho Chemical Industry, surfactant) The above components were uniformly dissolved and mixed to obtain 100 parts of an emulsion.

Formulation Example 3 [Dust] Compound No. A-3 0.6 part Compound No. B-3 1.4 parts Diatomaceous earth 20 parts Talc 78 parts The above were mixed and uniformly mixed and pulverized to obtain 100 parts of dust.

Formulation Example 4 [Flowable Agent] Compound No. A-7 10 parts Compound No. B-1 15 parts Methylcellulose 0.3 parts Colloidal silica 1.5 parts Sodium lignin sulfonate 1 part Polyoxyethylene nonylphenyl ether 2 parts Water 70.2 parts The above is well mixed and dispersed, and the slurry mixture is wet pulverized. Thus, 100 parts of a stable flowable agent was obtained.

Formulation Example 5 97 parts of clay (trade name: Zyklite, manufactured by Zyklite Industry) as a carrier, and alkylaryl sulfonate (trade name: Neoperex, manufactured by Kao Atlas Co., Ltd.) as a surfactant 1.5 Parts and 1.5 parts of nonionic and anionic surfactants (trade name: Solpol 800A, manufactured by Toho Chemical Industry Co., Ltd.) were uniformly pulverized and mixed to obtain a carrier for a wettable powder. 90 parts of this wettable powder carrier and the triazine derivative (Compound Nos. A-1 to A-7) 10 shown in Table 1
Part or the chloroacetamide herbicides shown in Table 2 [Compound No. [B-1 to B-3] 10 parts were uniformly pulverized and mixed to obtain a wettable powder. In addition, a carrier for a wettable powder containing the triazine derivative obtained above and a carrier for a wettable powder containing a chloroacetamide herbicide are mixed in a predetermined amount (active ingredient amount) and uniformly mixed and ground. To obtain a wettable powder.

Example 1 [Soil Treatment Test] Weed seeds of crabgrass clover, harlotine, Malva morning glory and crop seeds of corn and sorghum were sown in a 1/2000 arel Wagner pot filled with upland soil. The above formulation example 5 after sowing and before germination of seeds of weeds and crops
The predetermined amount of the herbicide obtained in (3) was suspended in water, and sprayed uniformly on the soil surface with a liquid amount equivalent to 100 liter / 10 are. Then, the plants were grown in a greenhouse, and on the 30th day after the treatment, crop phytotoxicity and herbicidal effect were evaluated according to the following criteria. The results are shown in Table 3.

[0039]

[Table 4]

[0040]

[Table 5]

[0041]

[Table 6]

The criteria for determining the herbicidal effect in Table 3 are as follows. (Judgment criteria) Degree of herbicidal effect Herbicidal effect (killing rate) 0 Less than 5% (almost no effect) 15-20% 2 20-40% 3 40-70% 4 70-90% 5 90% or more (almost complete) However, the above-mentioned herbicidal rate is obtained by measuring the above-ground vegetation weight of the chemical treatment area and the above-ground vegetation weight of the non-treatment area, and using the following mathematical formula 1
It was obtained by.

[0043]

[Equation 1]

The phytotoxicity in Table 3 was evaluated according to the following 6 grades. Degree of phytotoxicity 0 ...... No phytotoxicity to crops 1 ...... No phytotoxicity to crops 2 ...... To some phytotoxicity to crops 3 ...... To phytotoxicity to crops 4 ...... To phytotoxicity to crops Remarkable 5: Almost all crops die

From the results shown in Table 3, several samples were extracted, and the synergistic effect between the triazine derivative and the chloroacetamide herbicide was examined for crabgrass and velvetleaf by the following method. Specifically, it was evaluated by Q _E (expected value) obtained from the following mathematical formula 2.

[0046]

[Equation 2]

In Equation 2, Q _a , Q _b , and Q _E
Is as follows. Q _a : Only the triazine derivative as an active ingredient, ag /
10 measured value of herbicidal rate when treated at a liquid amount of Earle equivalent (%) Q _b: only chloroacetamide herbicides as active ingredients, found the herbicidal rate when treated at a liquid amount of bg / 10 ares equivalent Value (%) Q _E : Expected value [Source: Limpel, LE, PH Schuldt and D. Lamont,
Proc. NEWCC, 16, 48-53 (1962))

Here, if the measured value (herbicidal rate) of the herbicide obtained by mixing the triazine derivative and the chloroacetamide herbicide is larger than Q _E (expected value), there is a synergistic effect on the herbicidal activity. It has been expressed. The results are shown in Table 4.

[0049]

[Table 7]

Example 2 [Field test (soil treatment test)] A test plot having an area of 2 m ² per plot was prepared, and weed seeds of crabgrass, green foxtail, velvetleaf, purslane, periwinkle, ebisu, amaranth, and corn,
Sorghum crop seeds were sown at the same time. Then, before germination of corn, sorghum and weeds, a predetermined amount of the diluted solution of the herbicide obtained in Formulation Example 5 above was sprayed uniformly on the soil surface in a liquid amount equivalent to 20 liters / 10 ares.
This test was conducted in triplicate. After 60 days from the spraying of the chemicals, the surviving weeds were cut out from the above-ground part, the fresh grass weight was measured, and the average weeding rate of the 3 plots was calculated from the following mathematical formula 3. Also, for maize and sorghum, the weed weight of the above-ground part was measured in the same manner as the weeds, and the degree of phytotoxicity (weed control rate) was calculated. The results are shown in Table 5.

[0051]

[Equation 3]

[0052]

[Table 8]

[0053]

INDUSTRIAL APPLICABILITY The herbicidal composition of the present invention produces a high synergistic effect when a triazine derivative and a chloroacetamide herbicide are used in combination as an active ingredient, and exhibits a high herbicidal effect at a low dose and a wide range. Has a grass-killing spectrum. Further, the herbicidal composition of the present invention is highly safe for crops and does not cause phytotoxicity on crops.

Claims (1)

[Claims] 1. A compound represented by the general formula [I]: [Wherein A is the following formula (a): (However, Z represents an oxygen atom or a sulfur atom.) Or the formula (b): (However, X ² represents a methyl group or a fluorine atom, n represents an integer of 0 to 2), R ¹ represents a hydrogen atom or a methyl group, and X ¹ represents a fluorine atom or a chlorine atom. ] The triazine derivative represented by the following formula [II]-
[Chemical 4] A compound represented by the following formula [II]- And a compound represented by the following formula [II]- A herbicidal composition comprising, as an active ingredient, one of chloroacetamide herbicides selected from the group consisting of compounds represented by: