JPH01216905A - Herbicide composition - Google Patents

Abstract

PURPOSE:To obtain a herbicide composition effective against wide variety of weeds, especially for the weeding of orchard, at a low rate of application without causing the problem of acute toxicity, by using a novel benzohydroximic acid derivative and N-phosphonomethylglycine, etc., as active components. CONSTITUTION:The objective composition contains (A) a compound selected from 2-nitro-5-(substituted-phenoxy)benzohydroximic acid derivative of formula I (R<1> is lower alkyl; R<2> is H or lower alkyl; Z is -OR<3> or -SR<4>; R<3> is lower alkenyl or lower alkynyl; R<4> is lower alkyl) (novel compound) and (B) one or more compounds selected from N-phosphonomethylglycine, ammonium-(3- aminocarboxypropyl)-methylphosphinate, etc., as active components. The amount of the compound of formula I is 0.1-0.4 pts.wt. per 1 pt.wt. of the component B. The compound of formula I can be produced e.g., from a compound of formula II and a compound of formula Z-H.

Description

[Detailed description of the invention] Technical field The present invention relates to herbicidal compositions.

More specifically, the present invention comprises the following component (A) and component (B).
) as an active ingredient.

Component (A) General formula (1) (where Bl is a lower alkyl group, R2 is a hydrogen atom or a lower alkyl group, 2 is a group -0R3 or a group -8R4, and R3 is a lower alkenyl group or a lower alkynyl group) These may each be substituted with I.logen, a cyano group, or a lower alkoxycarbonyl group, and R4
2- represents a lower alkyl group, respectively)
Component (B) N-phosphonomethylglycine, ammonium-(3-aminocarboxyprobyl)-methylphosphinate and (2 -amino-4-methylphosphinobutyryl)alanylalanine.

The present invention provides a non-selective foliar treatment type herbicidal composition that has an extremely broad herbicidal spectrum and a high synergistic herbicidal effect with a reduced amount of effective system usage.

Prior Art The general formula (I) used in the present invention, (wherein R1 is a lower alkyl group, R2 is a hydrogen atom or a lower alkyl group, 2 is a group -0R3 or a group -8R', and R3 is a lower alkenyl group) or a lower alkynyl group, each of which may be substituted with /.rogen, a cyano group or a lower alkoxycarbonyl group, R
4 represents a lower alkyl group, respectively)
-Nitro-5-(substituted phenoxy)benzohydroxymic acid derivatives are novel compounds that have not been described in any literature, and have already been proposed in Japanese Patent Application No. 61-315442 and No. 61-315443.

N-phosphotumederglycine (hereinafter sometimes referred to as glyphosate) used as component (B) of the present invention is described in JP-A-54-100325, etc. as ammonium-(3-aminocarboxyprobyl)-methyl Phosphinate (hereinafter sometimes referred to as glufosinate) is
(sometimes referred to as JP-A-52-1 Beer Laf Male) is
These are known compounds proposed in JP-A No. 54-67026 and the like.

Problems to be Solved by the Invention Bipyridylium herbicides such as paraquat are used as non-selective herbicides. This drug has extremely high acute toxicity, and careful precautions and measures are required to prevent accidents when using it, but accidents frequently occur. Therefore, there is a strong need for a non-selective herbicide that does not have toxicity problems and has excellent herbicidal effects in place of paraquat and the like.

In addition, the compounds glyphosate, glufosinate, and bialafuos used as component (B) in the present invention are all already known as useful non-selective herbicides, but the effective amount used is high and the cost required for weeding is extremely high. There is a problem.

Effects of the Invention The herbicide composition of the present invention is a foliar treatment type non-selective herbicide, has no problem of acute toxicity, and can be used over a wide range of areas by greatly reducing the amount of effective dosage required in the past. It can kill several types of weeds, and since it is inactivated in the soil, it can be used for weeding before sowing or transplanting crops, and for weeding undergrowth in orchards.

Summary of the Invention The present invention provides a herbicidal composition containing the following components (A) and (B) as active ingredients.

Component (A) General formula (1) (where R1 is a lower alkyl group, B2 is a hydrogen atom or a lower alkyl group, 2 is a group -0R3 or a group -8R4, and R3 is a lower alkenyl group or a lower alkynyl group) and each of these may be substituted with a rogene group, a cyan group, or a lower alkoxycarbonyl group, R4
2- represents a lower alkyl group, respectively)
One or more compounds selected from nitro-5-(substituted phenoxy)benzohydroxymic acid derivatives, Component (B) N-phosphotumedelglycine, ammonium(3-aminocarboxyprobyl)-methylphosphinate and (2- one or more compounds selected from amino-4-methylphostisophinopsis) alanylalanine.

! Component (A) used in the present invention is a new compound that has not been described in any literature, and the present inventors have already filed a patent application in Japanese Patent Application No. 61-31544.
This is proposed in No. 2 and No. 61-315443. The main parts are described below.

General formula (1) (where R1 is a lower alkyl group, R2 is a hydrogen atom or a lower alkyl group, 2 is a group -0R3 or a group -8R', and t is a lower alkenyl group or a lower alkynyl group. In the 2-nitro-5-(substituted phenoxy)benzohydroxymic acid derivatives represented by (respectively, these may be substituted with a halogen, a cyano group or a lower alkoxycarbonyl group, and R4 represents a lower alkyl group) , "lower alkyl" may be linear or branched, such as methyl, ethyl, n-propyl, 1ao-propyl, n-butyl, 5ee-butyl, 1ao-butyl, n-pentyl, age-pentyl, n-hexyl and the like. Furthermore, the "lower alkenyl group" may also have a branched chain, such as vinyl, allyl, methallyl, crotyl, etc.
Examples of lower alkynyl groups include propargyl, 2-butenyl, and the like.

"Halogen atom" includes fluorine, chlorine, bromine and iodine, with chlorine being particularly preferred. Furthermore, r lower alkoxycarbonyl jii, the lower alkynyl group is a (lower alkyl)-O-CO- group having the above meaning,
For example, methoxycarbonyl, ethoxycarbonyl, n-
Globogysicarbonyl, 1-70 boxycarbonyl, n
-butoxycarbonyl and the like.

As the component (A) used in the present invention, the above formula (
In the above compound, R1 is preferably methyl, and R2 is preferably a hydrogen atom. Further, W is preferably allyl or propargyl, and R4 is preferably C1-3 alkyl.

The compound of formula (1) above has an asymmetric carbon atom and can exist in dextrorotatory, levorotatory or racemic form. In addition, the compound of formula (1) has two stereoisomers (syn type and an
ti form), it should be understood that formula (1) includes both of these two stereoisomers.

(syn'Ijl) (anti type) Although there is almost no difference in herbicidal activity between these two stereoisomers, syn'Ijl is considered to be more suitable in terms of mutagenicity.

- a compound of formula (I), for example: (a) in which R1 and R2 are as defined above;
represents an oxygen or sulfur atom, or (b) reacts an ester-forming derivative of a compound of the formula 2 (...) in which zFi is as defined above; A compound of the formula R"X" or R'X" (■) in which R3 and R4 are as defined above; f represents a halogen atom, or (C) a compound of the formula By reacting a compound of formula %, where R2 and 2 are as defined above, with a compound of formula %, where R1 is as defined above: X2 removes an acid residue. can be manufactured.

In the above (a), the ester-forming reactive derivatives of the compound of formula (If) include, for example, halides, acid anhydrides, etc. It can be easily produced by reacting a dehydrating agent such as acetic acid anhydride, a haloformic acid ester, etc. by a method known per se.

The reaction of the halide of the compound of formula (II) with the alcohol or thiol of formula (III) is generally carried out in the presence of a base,
It can be carried out in an inert organic solvent. At that time, E(
The amount of alcohol or thiol used in 1) is not strictly limited and can be varied widely depending on the reaction conditions and the yield of alcohol or thiol, but in general, the amount of halide 1 of the compound of formula (II) is 1 to 3 moles per mole,
Preferably, it is used in a proportion of 1 to 1.5 moles. Also, the amount of base used is not critical and can be varied over a wide range, but usually for the compound of formula (If)...
A range of 1 to 3, preferably 1 to 1.5 equivalents per mole of ride is advantageous.

The reaction temperature is generally from 0°C to the reflux temperature of the reaction mixture, preferably from 0 to 40°C.

Examples of solvents that can be used include aromatic hydrocarbons such as benzene and toluene; ethers such as tetrahydrofuran and dioxane; organic solvents such as acetone, acetonitrile, dimethylformamide, and dimethyl sulfoxide, and mixtures thereof; An example is a mixed solvent of water and water. Examples of the bases include tertiary amines such as pyridine and triethylamine; sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, and sodium hydride. .

Formula (II
) can be easily prepared by the method disclosed in JP-A No. 57-122045, where R2 is as defined above and W represents a lower alkoxy group. (2) to produce the compound (II) in which R1, R2 and W are as defined above, and further hydrolyze the compound (II) by a conventional method to produce the formula (
The compound of If) is obtained.

The compound of formula (■') is produced by reacting the compound of formula (v') with the compound of formula (■) in a suitable organic solvent in the presence of a base. This reaction is generally carried out under water cooling or at the reflux temperature of the reaction mixture, preferably at room temperature to about 80°C. The ratio of the compound of formula (M) to the compound of formula (V') is not critical and can vary widely, but generally 1 to 3 moles of the compound of formula (■), preferably 1 to 3 moles of the compound of formula (■) per mole of the compound of 2ω. It is appropriate to use it in a range of 1 to 2 moles. Further, the base is usually used in an amount of 1 to 3 equivalents, preferably 1 to 2 equivalents, per mole of the compound of formula (V).

Examples of solvents used in this reaction include alcohols such as methanol and ethanol; aromatic hydrocarbons such as benzene and toluene; ethers such as tetrahydrofuran and dioxane; acetotritolyl, dimethylformamide, dimethylsulfoxide, etc. Examples include one or more of these organic solvents and a mixed solvent of these solvents and water.

Examples of the base used in the above reaction include tertiary amines such as pyridine and triethylamine; sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate,
Examples include sodium ethylate and sodium hydride.

Alternatively, the reaction can be carried out in a two-layer system, in which case quaternary ammonium salts such as tetramethylammonium bromide, tetramethylammonium bromide, benzyltributylammonium bromide, quaternary phosphonium salts such as tetraphenylphosphonium bromide, etc. of phase transfer catalyst to the compound of formula (V), for example 1 to 5
It can be carried out using 0 wt9b, preferably 5 to 30 wt.

In any of the above embodiments (a), (b), and (c), after the reaction is completed, the reaction mixture is poured into water and treated according to conventional methods such as extraction with an organic solvent, recrystallization, column chromatography, etc. , above - isolating the compound of formula (1),
Can be purified.

A production example of the compound of general formula (1) used in the present invention is shown below.

Example 1: Methyl 0-methylthiocarbonylmethyl
5-(2-chloro0-4-trifluoromethylphenoxy)-2-nitrobenzohydroxymate (Compound AI)
Production [according to (a)] Methyl 〇-hydroxymethyl 5-(2-chloro-4
1.09 (2.23 mmol) of -trifluoromethylphenoxy)-2-nitropenzohydroxymate are dissolved in thionyl chloride 2d and heated under reflux for 1 hour. Excess thionyl chloride is distilled off to obtain acid chloride.

15% methyl mercaptan Na salt aqueous solution 1.25f (
2.68 mmol) was covered with ether 51LI, and the solution of the acid chloride obtained above in ether 5- was added dropwise over about 10 minutes while stirring under water cooling. Thereafter, the mixture was stirred at room temperature for 1.5 hours, and the ether layer was separated and dried over magnesium sulfate. After removing the desiccant from F, the ether was distilled off, and the resulting solid was recrystallized from ethanol to obtain the target compound Tsuta 1 (anti type, yield [1690jIv, yield 64.7%).

The diphenyl ether derivatives used in the present invention, which were synthesized by the same method as in the above-mentioned examples, were synthesized as compounds 2-xI of 21.
Show K.

Real JtfF12: Medel 0-allyloxycarbonylmethyl 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzohydroxymate (compound 12) production [according to (b)] Methyl 〇-carboxymethyl 5 -(2-chloro-4
-) Lifluoromethylphenoxy)-2-nitropenzohydroxymer~) 1.0? (2,23 mmol), 0.19 f (2,26 mmol) of sodium hydrogen carbonate, 0.5
After addition of 4 t (4.46 mmol), the mixture is stirred overnight at room temperature. The reaction mixture was poured into about 100 d of ice water, extracted twice with 204 ml of methyl acetate, washed with saturated brine, and dried over magnesium sulfate. After separating the desiccant with F, the solvent was distilled off and the resulting oily substance was purified by column chromatography (silica gel-n-hexane-acetic ether 4:1) to obtain the target compound 412 (antiW, yield fIk750
Cape, yield 68.9%).

The diphenyl ether derivatives used in the present invention, which were synthesized by the same method as in the above-mentioned examples, were synthesized using compound stores 13 to 2 in Table 1.
6.

(Left below) Example 3: Methyl 0-methylthiocarbonylmethyl
5-(2-chloro0-4-trifluoromethylphenoxy)-2-nitrobenzohydroxymate (compound AX
, ayn type) [by (C)] Methylthiocarbonylmethyl 5-(2-chloro1:l-
4-)Lifluoromethylphenoxy)-2-nitrobenzohydroxamate 1.0 f (2.14 mmol)
, diazomethane (5,4
An ether solution (10 g of ether) of 4 mmol) was added dropwise, and after stirring for 5 minutes, the solvent was distilled off. The desired compound was obtained by purification (
yield: 22%).

mp88-89℃ nmr 2.28 (3H,!+) 3.93 (3I
(, 11) 4.59 (2H, @) 6.88-8.1
2 (6H1m) Real M? FQ4: Production of mether O-allyloxycarbonylmethyl 5-(2-10-4-trifluoromethylphenoxy)-2-nitrobenzohydroxymate (compound 412, manufactured by syn) [according to (C)] Allyloxycarbonylmethyl 5 -(2-chloro-4
-) IJ fluoromedelphenoxy)-2-nitrobenzohydroxamate 1. Of (2,10 mmol)
, diazomethane (5,4
After stirring for 5 minutes, the solvent was distilled off, and the resulting oily substance was subjected to column chromatography (silica gel-n-hexane-
The target compound was obtained by purification using ethyl acetate (2:1).

(Yield 0.76 f, yield 74%) nmr 3.9G (3H, s), 4.55 (s, 2
)()4.5o(za,d),5.07-5.40(
2H.

m), 5.60-6.11 (IH, m), 6.90-
s, lo (eu, m) n = 1.5438 Among the compounds listed above, especially compounds M1, M4, M12
and Grave 23 are preferably used as component (A).

Component (B) used in the present invention is N-phosphonomethylglycine, ammonium-(3-aminocarboxyprobyl)-methylphosphinate and (2-amino-4-
One or more compounds selected from methylphosphinobutyryl) alanylalanine.

The herbicidal composition of the present invention comprises emulsifying, dispersing, wetting the active ingredient with a carrier consisting of a known liquid diluent, and
By using surfactants and other adjuvants for the purpose of spreading, binding, adjusting disintegration, stabilizing the active ingredient, improving fluidity, and preventing rust, formulations that are commonly used as agricultural chemicals, such as emulsions and irrigation It is used as y4M in agents or flowable agents. It can also be mixed or used in combination with other agricultural chemicals such as fungicides, insecticides, acaricides, herbicides, plant growth regulators, fertilizers, soil conditioners, etc.

Examples of the liquid diluent include paraffinic or naphthenic hydrocarbons such as kerosene, mineral oil, spindle oil, and white oil; aromatic hydrocarbons such as benzene, triene, xylene, ethylbenzene, cumene, and methylnaphthalene; carbon tetrachloride; and chloroform. , trichlorethylene, monochlorobenzene, O-chlorotoluene; ethers such as dioxane, tetrahydrofuran; ketones such as acetone, methyl ethyl ketone, diyne butyl ketone, cyclohexanone, acetophenone, isophorone; ethyl acetate, amyl acetate , ethylene glycol acetate, ethylene glycol acetate, diptyl maleate, diethyl succinate, and other esters; methanol, n-hexanol, ethylene glycol, diethylene glycol, cyclohexanol, benzyl alcohol, and other alcohols; ethylene glycol ethyl ether , ether alcohols such as ethylene glycol phenyl ether, diethylene glycol ethyl ether, and diethylene glycol butyl ether; polar solvents such as dimethyl formamide and dimethyl sulfoxide, and water.

Examples of surfactants used can be nonionic, anionic, cationic and zwitterionic, but typically nonionic and/or
Anionic substances are used. Suitable nonionic surfactants include, for example, those obtained by polymerizing and adding ethylene oxide to higher alcohols such as lauryl alcohol, stearyl alcohol, and oleyl alcohol; those obtained by polymerizing and adding ethylene oxide to alkylphenols such as isooctylphenol and nonylphenol; butyl Products obtained by polymerizing and adding ethylene oxide to alkyl naphthols such as naphthol and octylnaphthol; products obtained by polymerizing and adding ethylene oxide to higher fatty acids such as palmitic acid, stearic acid, and oleic acid; mono- or dialkyl compounds such as stearyl phosphate and dilauryl phosphate. Products obtained by polymerizing and adding ethylene oxide to phosphoric acid; Products obtained by polymerizing and adding ethylene oxide to amines such as dodecylamine and stearic acid amide; Products obtained by polymerizing and adding ethylene oxide to higher fatty acid esters of polyhydric alcohols such as nlu and tan ; Examples include those obtained by polymerization addition of ethylene oxide and propylene oxide. Suitable ionic surfactants include, for example, alkyl sulfate salts such as sodium lauryl sulfate and oleyl alcohol sulfate amine salt; alkyl sulfonate salts such as sodium sulfosuccinate dioctyl ester and sodium 2-ethylhexene sulfonate; Sodium isoprobylnaphthalene sulfonate, sodium methylene bisnaphthalene sulfonate, sodium lignin sulfonate, sodium dodecylbenzenesulfonate '4-1
Examples include lignosulfonate.

Furthermore, in order to improve the properties of the formulation of the herbicidal composition of the present invention and increase the herbicidal effect, high-quality ingredients such as casein, gelatin, albumin, glue, alginate, carboxymethylcellulose (CMC), methylcellulose, hydroxyethylcellulose, polyvinyl alcohol, etc. Molecular compounds and other adjuvants can also be used in combination.

The above-mentioned carriers and various auxiliary agents can be used individually or in combination as appropriate depending on the purpose, taking into account the dosage form of the preparation, the application situation, etc.

Although the active ingredient content of the herbicidal composition of the present invention in the various formulations obtained in this way varies depending on the formulation, the total amount of component (A) and component (6), 0
．． It is 1 to 99% by weight, preferably 1 to 80% by weight.

Emulsions usually contain 1 to 30% by weight of active ingredient compounds, for example.
This includes about 5 to 200 parts by weight of an emulsifier, the remainder being a liquid carrier, and a rust inhibitor added if necessary.

Irrigation agents usually contain, for example, 25 to 90% by weight of active ingredient compounds, with the remainder being solid carriers and dispersing wetting agents, with protective colloid agents, thixotropic agents, antifoaming agents, etc. being added as necessary.

Flowable agents usually contain 1 to 3 active ingredients, for example.
Contains 0% by weight, about 5 to 20% by weight of surfactant, and the remainder is water and optionally organic solvents, antifoaming agents, thickeners, antifreeze agents, preservatives, etc. is added.

The herbicide composition of the present invention comprises the above component (A) and component (B).
) as an active ingredient, and the proportion of component (A) used is preferably 0.01 part by weight or more, preferably 0.02 part by weight or more per 1 part by weight of component (B). Furthermore, 0.01 to 1 part by weight, preferably 0.025 to 1 part by weight, particularly 0.1 to 1 part by weight of the component per 1 part by weight of component (B).
It is preferable to add 0.4 parts by weight.

The application amount of the herbicide composition of the present invention is 100 to 2000
f/ha, preferably 200 to 1000 f/ha, and in this case, the effective dosage of component (A) is s to g
o o f/ha, preferably 25-200 f/ha
Dechiru.

The herbicide composition of the present invention is prepared within the above blending ratio range,
It is preferable to use the above-mentioned application amount because the synergistic herbicidal effect of component (A) and component (B) used in the present invention is particularly large. Of course, the above conditions can be selected and changed as appropriate depending on the type of target weed, growth stage, application location, application time, weather, etc.

The herbicide composition of the present invention can control various weeds growing in Ibara arable land and good arable land. For example, wild grass, black-and-white fern, red-winged grass, black-and-white fern, black-and-white fern, and the other two species, polygonum, pigweed, silverwort, whiteweed, morning glory, Japanese fir tree, pigweed, silverwort, American helium, American hornwort, Ebisu grass, Japanese brilliance, American king deer, Terrestrial plants such as oxalis, white chinese morning glory, chickweed, chinspermia, japonica, shepherd's purse, ash tree, yaemugura, hobby, chamomile, foxglove thistle, marigold, hotokenoza, isunofuguri, hymejong, harjon, wormwood, and aletheno chrysanthemum. Can control narrow-leaved and broad-leaved weeds. In addition, Nobie, Tamagayatsu 1 Cottonwood,
It can also control aquatic weeds and broad-leaved weeds such as Japanese azalea, Japanese staghorn, Kikashigusa, Japanese firefly, and Japanese pineweed.

The herbicide composition of the present invention is used not only in non-negative arable land but also in agricultural land where useful plants are planted, using a treatment method devised to prevent the chemical from coming into contact with the leaves and foliage of useful plants. (Direct 5play).

Next, some formulation examples of the herbicide composition of the present invention will be shown. "Parts" in the following formulations are based on weight.

Formulation Example L A homogeneous mixed solution of 32 parts of emulsion compound, 3 parts of polyoxyethylene styryl phenyl ether, 2 parts of sodium alkylbenzene sulfonate, and 2210 parts of xylene was added to 73 parts of a 20% glyphosate aqueous solution, and the mixture was heated using a homogenizer (rotation speed zs). The mixture was mixed and stirred for about 20 minutes at .ooorpm) to obtain a uniform emulsion, and then 10 parts of propylene glycol was added thereto and thoroughly shaken to obtain an emulsion.

Formulation Example 2 A homogeneous mixed solution of 215 parts of emulsion compound, 3 parts of polyoxyethylene steryl phenyl ether, 2 parts of sodium alkylbenzene sulfonate, and 2210 parts of After stirring the mixture for about 20 minutes at several 25.00 rpm to obtain a uniform emulsion, 1 G part of propylene glycol was added thereto and thoroughly shaken to obtain an emulsion.

Formulation Example λ A homogeneous mixed solution of 52 parts of emulsion compound, 3 parts of polyoxyethylene styryl phenyl ether, 2 parts of sodium alkylbenzene sulfonate, and 10 parts of xylene was added to 20% aqueous gTs part of Pear Ruff Off, and the mixture was heated using a homogenizer (rotation speed 25 The mixture was partially stirred for about 20 minutes at .

Formulation Example (No Formulation Example) Wettable powder 100 parts of a 30% glyphosate aqueous solution and 3 parts of alkylphenyl ether were dropped into a mixture of 39 parts of white carbon and 23 parts of clay, mixed well, and then dried with hot air at 50°C. Further, 13 parts of the compound and 2 parts of polyoxyethylene alkylamine were added and mixed well with stirring, and then finely pulverized using a jet mill (manufactured by Alpine) to obtain a wettable powder.

Formulation Example I Wettable powder glyphosate 18.5% water-soluble e, 162 parts and 3 parts of alkylphenyl ether were dropped into a mixture of 39 parts of white carbon and 20 parts of clay, mixed well, and then 5
It was dried with warm air at 0°C. Furthermore, 126 parts of Compound A and 2 parts of polyoxyethylene alkylamine were added and mixed with thorough stirring.
Subsequently, it was finely pulverized using a jet mill (manufactured by Alpine) to obtain an irrigation agent.

Formulation example a Wettable powder Via'') 100 parts of 30% aqueous solution of 7 male and 3 parts of alkyl phenyl ether are combined with 39 parts of white carbon and 33 parts of clay.
After mixing thoroughly, the mixture was dried with warm air at 50°C. Furthermore, 3 parts of Compound Layer 23 and 2 parts of polyoxyethylene alkylamine were added and mixed well, followed by finely pulverizing with a jet mill (manufactured by Albine) to obtain a wettable powder.

Formulation example 7. 494 parts of a flowable agent compound, 20 parts of glyphosate, 2 parts of polyoxyethylene nonylphenyl ether, 3 parts of dialkyl sulfosuccinate, 20 parts of a 1% CMC aqueous solution, 10 parts of propylene glycol, and 41 parts of water were mixed and placed in a wet ball mill. The mixture was crushed to obtain a flowable agent.

Formulation Example & Flowable Agent Mix 4 parts of Compound 419, 20 parts of glyphosate, 2 parts of polyoxyethylene nonylphenyl ether, 3 parts of dialkyl sulfosuccinate, 20 parts of 1% CMC aqueous solution, 10 parts of propylene glycol, and 41 parts of water. The mixture was ground in a wet ball mill to obtain a flowable agent.

Formulation Example: 204 parts of flowable agent compound layer, 20 parts of Bialafosu, 2 parts of polyoxyethylene nonylphenyl ether, 3 parts of dialkyl sulfosuccinate, 20 parts of 1% CMC aqueous solution, 10 parts of propylene glycol and 41 parts of water were mixed, It was ground in a wet ball mill to obtain a flowable agent.

Test example Weeding effect test by foliage treatment Square pot (30c+++X 30c! IIX 901
In 1), the field was filled with soil damage, and fixed amounts of various weed seeds shown in Table 2 were sown, and each plant was grown in a greenhouse until it had 3 to 6 leaves.

For drug release, the herbicide composition of the present invention prepared as an aquarium according to Formulation Examples 4 to 6 was used as a spreading agent in an amount of the active ingredient shown in Table 2, using "Surfactant WK" (Kao Corporation). The solution was diluted with water containing 0.25% of the product (manufactured by M.D. Co., Ltd.) and uniformly sprayed on the leaves and foliage at a spraying rate of 500 t/h.

21 days after the chemical spraying, the herbicidal effect on each weed was determined according to the following criteria, and the results are shown in Table 2.

(Margin below) Evaluation criteria (11 steps) Table 2 Clothes 2 continuation Table 2 continued Patent applicant: Mitsubishi Yuka Co., Ltd. Agent: Patent Attorney Masahisa Nagatani Agent Patent Attorney Takaya Yamamoto

Claims (1)

[Claims] (1) A herbicide composition containing the following components (A) and (B) as active ingredients. ￥Component (A)￥ General formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼...(I) (Here, R^1 is a lower alkyl group, R^2 is a hydrogen atom or a lower alkyl group , Z is a group -OR^3 or a group -S
R^4, R^3 is a lower alkenyl group or a lower alkynyl group, each of which may be substituted with a halogen, a cyano group, or a lower alkoxycarbonyl group, and R^4 is a lower alkyl group, each One or more compounds selected from 2-nitro-5-(substituted phenoxy)benzohydroxymic acid derivatives represented by )-methylphosphinate and (2-amino-4-methylphosphinobutyryl)alanylalanine.