JPH01213208A - Herbicide composition - Google Patents

Abstract

PURPOSE:To obtain a herbicide composition capable of controlling extremely wide kinds of weeds with a small amount free from problems such as toxicity, containing a 2-nitro-(substituted pyridyloxy)benzohydroximic acid derivative and a specific compound. CONSTITUTION:A herbicide composition containing (A) a compound such as O-methoxycarbonylmethyl 5-(3-chloro-5-trifluoromethyl-2-pyridyloxy)-2-nitroben zohyd-roximate shown by the formula (R and R<1> are lower alkyl; R<2> is H or lower alkyl; X is H or halogen) and (B) a compound selected from N-phosphono methylglycine, ammonium-(3-aminocarboxypropyl)-methylphosphinate and amino-4- methylphosphinobutyryl)alanylalanine in the ratio of 0.01-1pt.wt., preferably 0.02-0.6pt.wt. component A and 1pt.wt. component B.

Description

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

More specifically, the present invention provides - formula (1), with the proviso that R
and R1 each represent a lower alkyl group, P represents a hydrogen atom or a lower alkyl group, and X represents a hydrogen atom or a halogen atom, 2-nitro-3-(substituted pyridyloxy)benzohydroxymic acid One or more compounds (ingredients) selected from derivatives
A)), and one type selected from N-phosphonometherglycine, ammonium-(3-7minocarboxyprobyl)-methylphosphinate, and (2-amino-4-methylphosphinobutyryl)alanylalanine The present invention relates to a herbicidal composition containing the above compound (component (B)) as an active ingredient.

The herbicide composition of the present invention can completely control a wide range of weeds, from annual to perennial weeds, at low doses;
Moreover, it is a groundbreaking product with no problems such as toxicity.

PRIOR ART The active ingredient (A) of the herbicidal composition of the present invention has the following formula: where R and R1 each represent a lower alkyl group, t represents a hydrogen atom or a lower alkyl group, and X represents a hydrogen atom or 2-nitro-3-(substituted pyridyloxy)benzohydroxymic acid derivative represented by , which represents a halogen atom, is a novel compound that has not been described in any literature.
It was previously filed as Japanese Patent Application No. 173888/1988.

The compound of component (B) used in the present invention is a known compound, and N-phosphonomethylglycine (hereinafter sometimes referred to as glyphosate) is disclosed in Belgian Patent No. 873198.
Ammonium-(3-aminocarboxyglobyl)-methylphosphinate (hereinafter sometimes referred to as glufosinate) is described in U.S. Pat. Showa 52
- sometimes written as lower bialafoss) is JP-A-1987-
67026, US Pat. No. 4,309,208, etc.

Problem to be Solved by the Invention Bipyridylium herbicides such as paraquat are used as non-selective herbicides, but these drugs have extremely strong acute toxicity and must be used with extreme caution to prevent accidents. Although countermeasures are necessary, unforeseen accidents involving birds occur frequently. For this reason, it is a non-toxic alternative to paraquat etc.
Furthermore, there is a strong need for non-selective herbicides with excellent herbicidal effects.

In addition, the compounds of component (B) used in the present invention, glyphosate, glufosinate, and pialafos, are all already known as useful non-selective herbicides, but the effective dosage is high and the cost required for weeding is extremely high. It has the problem of sticking.

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 in a herbicide with a greatly reduced effective dosage, which was previously required. It can kill a wide range of weeds, and since it is inactivated within ±1, 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 component (A): general formula (1), where R and R1 each represent a lower alkyl group, R2 represents a hydrogen atom or a lower alkyl group, and X represents a hydrogen atom or a halogen 18! selected from 2-nitro-3-(substituted pyridyloxy)benzohydroxymic acid derivatives represented by 18! The above compound and component (B): selected from phosphonomethylglycine, ammonium-(3-aminocarboxyglobyl)-methylphosphinate and (2-amino-4-methylphosphinobutyryl)alanylalanine. The present invention provides a herbicidal composition containing as an active ingredient one or more kinds of compounds.

The novel compound represented by the general formula (1) used in the present invention is described in detail in Japanese Patent Application No. 173.888/1988, but the main parts thereof will be described below. and as follows.

In the novel pyridylphenyl ether derivative represented by the general formula (1), the I-rodan atom of X is as follows:
Examples include fluorine, chlorine, bromine, or iodine. Among these, fluorine and chlorine are preferred.

As the lower alkyl group in R1, R2 and R,
A lower alkyl group having 1 to 5 carbon atoms is preferred, such as methyl, ethyl, n-propyl, i-propyl, n-butyl, S-butyl, i-butyl, n-amyl, and the like.

The compound represented by the above general formula (I) may be a stereoisomer (
5) rn and anti) and optical isomeric forms, and it should be understood that compounds of general formula (1) in these isomeric forms are within the scope of the present invention.

Among these examples, preferred examples of compounds of general formula (I) include compounds in which R1 is a methyl group, R2 is a hydrogen atom or a methyl group, and R is a lower alkyl group of Cx-Cs.

The compound represented by the formula (1) can be produced, for example, by the method shown below.

OR'' (II) [In the formula, X, R'', R2 and R have the same meanings as described above for general formula (I), and
08O2R'(R' is a substituted or unsubstituted alkyl group, phenyl group, or alkoxy group) bb. ] According to this embodiment, 2-nitro-3-(substituted pyridyloxy)benzoic acid (1) is converted into an acid chloride by a conventional method, for example, with thionyl chloride, and then, for example, in an organic solvent in the presence of a base. Hydroxamic acid derivatives (If) can be obtained by reaction with 0-substituted hydroxylamines.

In the reaction, the amount of thionyl chloride to be used can be selected and changed appropriately, but it is, for example, 1 to 10% based on the compound of formula (III).
Examples include amounts used such as equivalent amounts. The reaction temperature can also be selected appropriately, and examples thereof include temperatures ranging from room temperature to 80°C. In the reaction between the formed acid chloride and the 0-substituted hydroxylamine, the amount of the 0-substituted hydroxylamine can be appropriately selected, and can be exemplified by a 1 to 3 equivalent amount. The amount of the base can also be selected as appropriate, and for example, the amount used can be 1 to 3 equivalents.

At this time, the reaction temperature may be, for example, from room temperature to 100°C.

Examples of solvents used include aromatic hydrocarbons such as benzene and toluene; ethers such as tetrahydrofuran and dioxane; one or more organic solvents such as acetone; acetonitrile; dimethylformamide; dimethyl sulfoxide; and these solvents. An example is a mixed solvent of water and water.

Examples of the base include pyridine, trietheramine, sodium carbonate, potassium carbonate, and sodium hydrogen carbonate.

The 〇-substituted-2-nitro-3-(substituted pyridyloxy)benzohydroxymic acid derivative (II
) and the alkylating agent (II/) or CHxNz in an organic solvent in the presence or absence of a base to produce the hydroximic acid derivative (1) used in the herbicide of the present invention.

The reaction is to react with compound (II) or CH
For example, 1 to 3 molar equivalents of 2N2, preferably 1 to 1.5
The reaction can be carried out using molar equivalents, for example, under water cooling or at the reflux temperature of the solution, preferably at room temperature to about 80° C., for 0.5 to 20 hours. Solvents used in this reaction include, for example, alcohols such as methanol and ethanol; aromatic hydrocarbons such as benzene and toluene; diethyl ether, tetrahydrofuran,
Examples include ethers such as dioxane; organic solvents such as acetone; acetonitrile; dimethylformamide and dimethyl sulfoxide; and mixed solvents of these solvents and water.

Examples of the base used in the above reaction include pyridine, triethylamine, sodium hydroxide, potassium hydroxide,
Examples include sodium carbonate, potassium carbonate, sodium ethylate, and sodium hydride. The deoxidizer is a compound (
For example, it can be used in an amount of 1 to 3 equivalents, preferably 1 to 1.5 equivalents, based on leopard, and the reaction can be carried out in a good yield, which is preferable.

Using CHsNz as the alkylating agent, there is no need to use a base when carrying out this reaction.

In addition, when the reaction is carried out in a two-phase system, phase transfer catalysts such as quaternary ammonium salts such as tetramethylammonium bromide, tetrabutylammonium bromide, penzoltributerammonium bromide, and quaternary phosphoniums such as tetraphenylphosphonium bromide are used. Compound (
V), for example 1 to 50 wt4, preferably 5
~30 wt'J can be used.

After completion of the reaction, the compound represented by the formula (I) can be isolated by, for example, treating the reaction mixture in water, extraction with an organic solvent, recrystallization, column chromatography, etc. according to conventional methods.

Next, a synthesis example of the compound represented by the general formula (1) will be described.

Synthesis Example L [Methyl 0-methoxycarbonylmethyl
5-(3-chloro-3-) I) Fluoromethi A-2-
Production of HI7 syloxy)-2-nitrobenzhydroxymate (compound product 32)] 5-(3-ri1) Rho 5
-) Lifluoromethyl-2-pyridyloxy)-2-nitrobenzoic acid 36.2P (0.10 mol) is dissolved in thionyl chloride 36.2- and heated under reflux for 1.5 hours. Excess thionyl chloride is distilled off to obtain the acid salt f.

Aminooxyacetic acid methyl ester 1 o, sr (0,1
mol), 10.1 t (0.1 mol) of triethylamine, and 300 d of dry ether to a solution of 150 d of the acid chloride obtained above was added dropwise over about 20 minutes while stirring under water cooling. Thereafter, the mixture was stirred for 30 minutes under water cooling and for 1.5 hours at room temperature. The reaction solution was poured into 300 d of ice water, extracted three times with 200 d of ethyl acetate, washed with saturated brine, and dried over magnesium sulfate.

After removing the drying agent, the solvent was distilled off and the resulting solid was recrystallized from triene to give methoxycarbonylmethyl 5-(3
-chloro-5-to17 fluoromethyl-2-pyridyloxy)-2-nitrobenzohydroxamate 37.2
f was obtained (yield 82.7%).

37.2 f of the hydroxamate obtained above was dissolved in a mixed solvent of 70 d of ether and 70 - of tetrahydrofuran, and 24.8 f of N-nitrone methyl urea was dissolved under stirring while cooling with water.
A solution of 300 dg of ether of diazomethane prepared from (0,241 mol) was added dropwise over about 40 minutes. Thereafter, the mixture is stirred for about 30 minutes under water cooling.

Excess diazomethane is decomposed with acetic acid, the solvent is distilled off, and the resulting solid is recrystallized from methanol to obtain the desired compound &
32 was obtained (27.Of, yield 70.4%). mp,
71.0-73.0°C (syn type).

The above compound 432 5.0 SF was dissolved in 200 d of toluene, degassed by bubbling nitrogen gas, and then irradiated with light for 3 hours using a high-pressure mercury lamp (Riko Kagaku Sangyo UVL-1009). The solvent was distilled off and the residue was purified by column chromatography (silica gel-n-hexane-acetic ether 2:1) to obtain the desired isomer (mti type) of compound 432 (3.
5? , yield 70.0 poly, mp, 84.5-85.5
℃).

Synthesis example 2. (Ether 0-methoxycarbonylmethyl 5-(3-chloro-5-trifluoromethyl-2-
Production of (pyridyloxy)-2-nitrobenzhydroxymate (compound 53) Hydroxamate 2.2 s t (5 mmol) obtained in the same manner as in Synthesis Example 1,
Anhydrous potassium carbonate 0.83 f (6 mmol), DM
The Flom oil suspension is heated to 65-67°C and 1.29 (6 mmol) of p-toluenesulfonic acid ethyl ester is added dropwise over about 15 minutes. Thereafter, the mixture was stirred at the same temperature for 1 hour. The reaction mixture was poured into about 150 d of ice water, extracted twice with 30 WI of ethyl acetate, washed with saturated brine, and dried over magnesium sulfate. After removing the desiccant, the solvent was distilled off and the resulting oily substance was purified by column chromatography (silica gel-n-hexane-acetate 421) to obtain the target compound &sa (synm) (1.4 t
, yield 58.5%). Table 1 shows the pyridyl phenyl ether al represented by the general formula (1) synthesized by the same method as in the above synthesis example.

(Left below) Table 1
4.0℃(syn) Z HCHs HCzHs l HCHz H2k -C3H74HCHs
H1-CaHy 5 HCH3Hn-Ca&mp, 55.0-56.
0℃(mti) & HCH3H1-C4He 7, HCHa H1-C4H9 & HCHs
Ht-C4Hs 9, HCH3Hn-C5H11 1a HCHa Ht-C5HuIL H
C& CHa CHslλ HCH3CH3C
2H5 11HCH3CH3n-C5Ht 14 HCH3CH31-C3H7 15, HCH3CH3n-C4H* l& ) (CH3CH3t-C4Hs17, HC
H3CHs n-C3H.

19, HCH3C2H5CHs 19, HCHa CzHs C2H527-H
CH3C2) [1n-C3H721HCH3CzHs
n-C4n522- HC2H5H(Es 21 HC2I(S HC2H527HC2
H5Hn-C2H5 27, H1-C3H7HCHs 26, H1-C3Hy HC2H527-Hi -
C3H7Hn-C4He2&HC2H5CHa
CH329-HC2H5C)tan-C4H9
30・H1-C3H7CH3CHs3L H1
-CaHy CH3n-C4Hs3t CL C
H3Hn-C3H7mp41.5-73.0℃ (ant
i) 3! L C1CHs Hi -C3H7mp,
97.5-99.0℃ (anti) 36L CL Cal3Hn -C4H9mp, 8
4.0-85.0℃ (anti) 37, CI CHs H1-C4Hs
mp, 77, s ~ 79.0°C (anti) 3a CL CH3H5-C4Hs39, CI
CH3Ht-C4Hs17 C1CHs
Hn-C5Hump-71,5~72.5℃(a
nti) 41, CtCHs Ht-C5H.

Add, 4 4L C1CHa CHs CHs
"D 1.5328 (syn) 43, CI CH3CH3C2H5 44CI CH3CH3n-C2H544, Cl
CH3CH31-C2H544,, CI CH3CH
3n-C4Hj47, Ct CHs CH
a t-C4Hs4&CI CHs C
H3n-C5H1t49- CI CHs
C2H5(I(350, CL CH3C2H5Cz几51, CL CHs C2H5n-CaH
ysZ CL CH3C2HJ, n-CaH*
1J 5 & CI C2H5HCHs no 1
．． 5359(syn) 54 C1C2H5HC2H5 55, CI, C2H5Hn-C<H921,1 5a C11-C3Hy HCH3nD1.533
6(syn) s7. C11-CsHt HC2H55&
CL 1-CaHy Hn-C4Hj59, CI
CxHs CHs CHs6α C1CxH
s CHs n-C4Hs61- CL
1-CaHy CHs CHs'L CL 1
-CaHy CHs n-C4&61 FC
Ha HC) is64 F CH3HC2
H5 6&p CHs Hn-C2H56&
li' CHa H1-CsHy''-F
CH3Hn-C4Hs 6 & F CHa Ht-C4H 6g,
F CH3H8-C4H9 Among the above compounds, those in which X is a chlorine atom, R1 is a methyl, t is a hydrogen atom, and R is a lower alkyl group are preferred, and those in which R is ethyl or ethyl are particularly preferred.

Ingredients <8) used in the herbicidal composition of the present invention are N-phosphotumederglycine, ammonium-(3-aminocarboxyprobyl)-methylphosphinate, and ( It is one or more compounds selected from 2-amino-4-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
For the purpose of spreading, binding, adjusting disintegration, stabilizing active ingredients, improving fluidity, preventing rust, etc., surfactants and other auxiliary agents are conveniently used to form formulations commonly used as agricultural chemicals, such as emulsions, It is prepared and used as a hydrating agent or a flowable agent. It can also be mixed or used in combination with other aphrodisiacs, such as fungicides, insecticides, acaricides, herbicides, plant growth regulators, fertilizers, soil conditioners, etc.

Examples of the liquid diluent include paraffinic or hexatene hydrocarbons such as kerosene, mineral oil, spindle oil, and white oil; aromatic hydrocarbons such as benzene, triene, xylene, ethylbenzene, cumene, and methylnaphthalene; and tetrachloride. Carbon; chloroform, trichlorethylene,
Chlorinated hydrocarbons such as monochlorobenzene and O-chlorotoluene; Ethers such as dioxane and tetrahydrofuran; Ketones such as acetone, ethyl ether ketone, diimbutyl ketone, cyclohexanone, acetophenone, and inphorone; ethyl acetate, amyl acetate, and ethylene Esters such as glycol acetate, diethylene glycol acetate, dibutyl oleate, and diethyl succinate; alcohols such as methanol, n-hexanol, ethylene glycol, diethylene glycol, cyclohexanol, and benzyl alcohol; ethylene glycol ether ether, ethylene glycol ether ether,
Examples include ether alcohols such as diethylene glycol ethyl ether and diethylene glycol butyl ether; polar solvents such as dimethyl formamide and dimethyl sulfoxide; and water.

Examples of surfactants that can be used include nonionic, anionic, cationic, and zwitterionic surfactants, but usually nonionic and/or
However, ionic 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; nibutyl; Products obtained by polymerizing and adding ethylene oxide to noalkylnaphthols 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; monomers such as stearyl fluoroic acid and dilauryl 9-phosphate, etc. Or those obtained by polymerizing and adding ethylene oxide to dialkyl phosphoric acid; those obtained by polymerizing and adding ethylene oxide to amines such as dodecylamine and stearic acid amide; those obtained by polymerizing and adding ethylene oxide to higher fatty acid esters of polyhydric alcohols such as norbitane; ; Examples include those obtained by polymerization addition of ethylene oxide and propylene oxide. Suitable anionic surfactants include, for example, alkyl sulfate ester salts such as sodium lauryl sulfate and oleyl alcohol sulfate amine salt; alkyl sulfonic acids such as sodium sulfosuccinate diocderester and sodium 2-ethylhexene sulfonate; Salt; Sodium isopropylnaphthalenesulfonate, Sodium methylenebisnaphthalenesulfonate') A,') Sodium geninsulfonate, Sodium dotecylbenzenesulfonate, etc.
7) 71J-rusulfonate and the like.

Furthermore, in order to improve the properties of the formulation of the herbicide composition of the present invention and increase its herbicidal effect, polymer compounds such as casein, gelatin, albumin, glue, alginate, carboxymedel cellulose, methyl cellulose, hydroxyethyl cellulose, and polyvinyl alcohol are added. and other adjuvants can also be used together.

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.

The active ingredient content of the herbicidal composition of the present invention in the various formulations thus obtained varies depending on the formulation, but for example, The amount is 0.1 to 99% by weight, preferably 1 to 80% by weight.

Emulsions contain, for example, the active ingredient compound in an amount of usually 1 to 30 parts (1 to 30 parts by weight).
This includes about 5 to 20% 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 the active ingredient compound, with the remainder being a solid carrier and a dispersing wetting agent, with protective colloid agents, chicktroping agents, antifoaming agents, etc. being added as necessary.

Flowable agents usually contain 1 to 3 active ingredients, for example.
This contains about 5 to 20 weight surfactants, and the rest is water, organic solvents, antifoaming agents, thickeners, antifreeze agents, preservatives, etc. as necessary. can be added.

The herbicide composition of the present invention comprises the above component (A) and component (B).
The ratio of use is 0.00 parts of the component (A) compound per 1 part by weight of the component (B) compound.
It is sufficient to use 0.01 weight part or more, preferably 0.02 weight part or more. Furthermore, usually 0.01 to 1 part by weight, preferably 0.02 to 0.6 part by weight, particularly 0.1 to 0.4 part by weight of the compound of component (A) per 1 part by weight of the compound of component (B). It is preferable to mix parts by weight.

The herbicide composition of the present invention is prepared within the above usage ratio range,
It is preferable to apply this method because the synergistic herbicidal effect of component (A) and component (B) used in the present invention is particularly large.

The herbicide composition of the present invention can control various weeds growing in non-agricultural land and agricultural land. For example, wild grass, black-tailed grass, foxtail grass, black-and-white grasshopper, black-and-white grasshopper, black-and-white flycatcher, Japanese barnyard grass, polygonum, pigweed, silverwort, yellowtail, morning glory, white-breasted fir, pigweed, purslane, American helium, American hornwort, yellowtail grass, staghorn grass, rockweed, golden deer, Oxalis, White-spotted butterfly, I. copae, Chiselweed, Tumefusa, Shepherd's shepherd, Tanetsukebana, Yaemugura, Hobby,
It can control terrestrial narrow-leaved and broad-leaved weeds such as chamomile, Ezono fox thistle, marigold, hotokenoza, dogfish puffer, hymejong, haljon, hymemukashi mugwort, and cypress chrysanthemum. Furthermore, aquatic narrow-leaved and broad-leaved weeds such as Japanese wild grass, Japanese cypress, Japanese cypress, Japanese azalea, Japanese chickweed, Japanese chickweed, Japanese fireweed, and Japanese grasshopper can also be controlled.

The herbicide composition of the present invention is used not only for weeding before sowing or transplanting of crops in non-agricultural land and cultivated land, but also for weeding the foliage of useful plants in agricultural land where useful plants are planted. A treatment method devised to prevent chemicals from coming into contact with the
ect 5pray) for convenience.

The application amount of the herbicide composition of the present invention can be appropriately selected depending on many factors, such as the type of weed to be weeded, the growth stage, the application site, the application time, and the weather.
The total applied active ingredient amount of A) and component (B) is 100
~150 Of/ha, preferably 200-1000
r/ha. Furthermore, - 5 to 600 flh as an effective dosage of the compound of component (A) represented by formula (I)
&1 Preferably 25 to 200 f/ha.

Next, several embodiments of formulation examples of the herbicidal 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 372 parts of emulsion compound A, 3 parts of polyoxyethylene steryl phenyl ether, 2 parts of sodium alkylbenzene sulfonate, and 10 parts of xylene was added to 73 parts of a 20% aqueous solution of glyphosate, and heated using a homogenizer (rotation speed: 25. After stirring for about 20 minutes at 0.00 rpm) to obtain a uniform emulsion, 10 parts of propylene glycol was added thereto and thoroughly shaken to obtain an emulsion.

Formulation Example 2 A homogeneous mixed solution of 355 parts of emulsion compound A, 3 parts of polyoxyethylene steryl phenyl ether, 2 parts of sodium alkylbenzene sulfonate, and 10 parts of xylene was added to 70 parts of an 18.5% aqueous solution of glyphosine, and heated using a homogenizer (rotation speed). After stirring for about 20 minutes at 25.00 Orpm 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 532 parts of the emulsion compound, 3 parts of polyoxyethylenestyrylphenyl 7", 2 parts of sodium alkylbenzene sulfonate, and 2210 parts of xylene was added to 73 parts of an aqueous solution of Piarafuos 20F, and the mixture was heated using a homogenizer (rotating). After stirring for about 20 minutes at several 25.00 Orpm to obtain a uniform emulsion, 10 parts of propylene glycol was added thereto and thoroughly shaken to obtain an emulsion.

Formulation Example: 1 too part of a 30% aqueous solution of glyphosate (wettable powder) and 3 parts of an alkyl phenyl 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, 323 parts of Compound Mu and 2 s of polyoxyethylene alkylamine were added and mixed well with stirring, and then finely pulverized using a jet mill (manufactured by Albine Co., Ltd.) to obtain an irrigation agent.

Formulation Example & Irrigation Agent Glyphosine) 162 parts of an 18.5% aqueous solution and 3 parts of alkylphenyl ether were dropped into a mixture of 39 parts of white carbon and 20 parts of clay, and after mixing well, 5 parts of this was added.
It was dried with warm air at 0°C. Further, 366 parts of the compound and 2 parts of polyoxyethylene alkylamine were added and mixed with thorough stirring.
Subsequently, the mixture was finely pulverized using a jet mill (manufactured by Alpine) to obtain a wettable powder.

Formulation Example Wettable powder 100 parts of a 30% aqueous solution of Piarafoff and 3 parts of alkylphenyl ether were dropped into a mixture of 39 parts of white carbon and 33 parts of clay, mixed well, and then dried with hot air at 50°C. Furthermore, 333 parts of Compound Black and 2 parts of polyoxyethylene alkylamine were added and mixed well, followed by finely pulverizing with a jet mill (manufactured by Albine) to obtain an irrigation agent.

Formulation Example L 354 parts of flowable agent compound, 20 parts of glyphosate, 2 parts of polyoxyethylene nonylphenyl ether, 3 parts of dialkyl sulfosuccinate, 20 parts of 1% carboxymethine cellulose (CMC') aqueous solution, 10 parts of propylene glycol
1 part and 41 parts of water were mixed and ground in a wet ball mill to obtain a flowable agent.

Formulation example & Flowable agent 404 parts of compound A, 20 parts of glyphonate, 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, and wet-type The mixture was ground in a ball mill to obtain a flowable agent.

Formulation Example I Mix 564 parts of flowable agent compound A, 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, and wet-process. The mixture was ground in a ball mill to obtain a flowable agent.

Test Example: Testing the herbicidal effect of foliar treatment Fill square pots (30cm x 30aRX 9c11) with field soil, sow a certain amount of the various weed seeds shown in Table 2, and grow in a greenhouse until each plant has 3 to 6 leaves. I let it happen.

In the chemical treatment, the herbicide composition of the present invention prepared as an aquarium according to Formulation Examples 4 to 6 was mixed with [Surf Actan] WKJ (Seisei) as a spreading agent in an amount of the active ingredient shown in Table 2. The solution was diluted with water containing 0.25% (manufactured by Kasei Chemical Co., Ltd.) and uniformly sprayed on the foliage at an amount of water equivalent to 500 A/ha.

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

Claims (1)

[Claims] (1) Component (A): General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(I) However, in the formula, R and R^1 each represent a lower alkyl group, and R^2 is a hydrogen atom. or a lower alkyl group, and X represents a hydrogen atom or a halogen atom, 2-nitro-5-(substituted pyridyloxy) represented by
one or more compounds selected from benzohydroxymic acid derivatives, and component (B): N-phosphonomethylglycine, ammonium-(3-aminocarboxypropyl)-methylphosphinate and (2-amino-4-methyl 1. A herbicidal composition comprising, as an active ingredient, one or more compounds selected from the group consisting of phosphinobutyryl) alanylalanine.