JPH02184606A - Herbicidal composition - Google Patents

Abstract

PURPOSE:To obtain the subject composition, containing a 2-nitro-5-(substituted pyridyloxy)benzohydroximic acid derivative and specific dinitroaniline derivative as active ingredients and having a great weeding spectrum with a small amount of chemical without phytotoxicity to cultivated crops. CONSTITUTION:A herbicidal composition obtained by containing (A) at least one of 2-nitro-5-(substituted pyridyloxy)benzohydroximic acid derivative expressed by formula I (R is lower alkyl) and (B) at least one dinitroaniline derivative selected from 3,4-dimethyl-2,6-dinitro-N-1-ethylpropylaniline and 2,6- dinitro-N,N-dipropyl-4-trifluoromethylaniline as active ingredients. The blending ratio of the active ingredients is 0.5-100 pts.wt., preferably 1-30 pts.wt., especially 1-10 pts.wt. ingredient (B) based on 1 pt.wt. ingredient (A). The content of the active ingredients in the composition is preferably 1-80wt.%.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to herbicidal compositions, and more particularly to herbicidal compositions comprising novel 2-nitro-5-(substituted pyridyloxy)benzohydroxyme derivatives and known dinitroaniline derivatives. The present invention relates to a herbicidal composition containing the combination as active ingredients, which has a wide herbicidal spectrum and can exhibit a sufficient herbicidal effect with a low dose.

A wide variety of herbicides have been developed through many years of herbicide research and development, and these herbicides are important materials for improving agricultural productivity, such as protecting useful crops from weeds and saving labor in farming. It has now become indispensable.

However, even today, there is still a demand for the development of herbicides that have superior herbicidal performance, that is, do not cause chemical damage to cultivated crops, have a broad herbicidal spectrum, and are effective at lower doses. However, existing herbicides do not necessarily fully meet these requirements.

For example, 3,4-dimethyl-2,6-dinitro-N-1-ditylprobylaniline (hereinafter referred to as "bendimetalin"), which is known as a dinitroaniline derivative herbicide - Belgian Patent No. 787939 (see specification) and 2,6-sinitro N,N-jig mouth pill-4-
Trifluoromethylaniline (hereinafter sometimes referred to as "trifluralin" - see U.S. Pat. No. 3,257,169) is used in cultivated crops such as corn, soybean, wheat, cotton, and sunflower by soil mixing treatment or soil treatment. Although it is a herbicide that is widely used for treatment, it is known that in its herbicidal spectrum, the above-mentioned compounds have poor herbicidal effects against weeds such as Asteraceae, Euphorbiaceae, Cyperaceae, Euphorbiaceae, Cyperaceae, Euphorbiaceae, and Cyperaceae. especially,
When the dinitroaniline derivatives mentioned above are used as herbicides in the cultivation of cereal crops, they can be used in limited amounts that do not cause chemical damage to useful crops.
Harmful weeds such as thistle and other harmful weeds are uncontrolled and overgrown, which is an important problem in crop production, and it is strongly desired that this point be improved.

The present inventors have conducted intensive research with the aim of developing a herbicide that overcomes the drawbacks of the dinitroaniline derivative herbicides, has a wide herbicidal spectrum, and can exhibit sufficient herbicidal effects at low doses. As a result of repeated efforts, we have now developed such dinitroaniline derivative herbicides using novel 2-nitro-5-(substituted pyridyloxy)benzohydroxymic acid derivatives of the type previously proposed (patent application). 1986-
The inventors have discovered that the above object can be achieved by combining the present invention with the above-described method (see specification No. 45738), and have completed the present invention.

Thus, according to the invention: (a) General formula (I) OCR.

(b) 3,4-dimethyl-2,6- Sinitro N-
Contains as an active ingredient at least one dinitroaniline derivative selected from 1-ditylpropylaniline (pendimethalin) and 2,6-sinitro-N,N-ziguchivir-4-trifluoromethylaniline (trifluralin). A herbicidal composition is provided.

The composition of the present invention, which is a combination of a dinitroaniline derivative and a 2-nitro-5-(substituted pyridyloxy)benzohydroxymic acid derivative represented by the general formula CI), has a wide herbicidal spectrum.
aparine), chamomile (Matricaria)
chamomilla), Ezono fox thistle (C
Harmful weeds such as P. irsium arvense can be easily controlled, and surprisingly, by using both compounds in combination, the dosage is much lower than when using each one alone. It was found that the herbicidal spectrum was expanded and that the combined use of both compounds produced a remarkable synergistic effect.

Thus, the composition of the present invention exhibits a synergistic herbicidal effect on weeds that are difficult to control, such as Japanese grasshopper, chamomile, and fox thistle, which were conventionally difficult to control with the sole use of dinitroaniline derivative herbicides. , the weeds can be effectively controlled without causing practically problematic phytotoxicity to cultivated plants. Moreover, it is also possible to considerably reduce the amount of active ingredients required for weed control, making it possible to provide a herbicide that is extremely useful in agriculture.

The above formula (I) used in the herbicidal composition of the present invention
2-nitro-5-(substituted pyridyloxy) represented by
Benzohydroxymic acid derivatives are new compounds that have not been published in previous publications, and details of their production method, physical properties, herbicidal activity, etc. are disclosed in the specification of previously filed Japanese Patent Application No. 63-45738. ing.

In the compound represented by formula (I), the lower alkyl group represented by R may be of any type, linear or branched, such as methyl, ethyl, n-propyl, is.

-propyl, n-butyl, 5ec-butyl, is.

-butyl, tert-butyl, n-pentyl, 1so-
Examples include alkyl groups having up to 6 carbon atoms such as amyl and n-hexyl.

The compound represented by the above formula (I) has stereoisomers (sy
It is to be understood that compounds of formula (2) can be in n- and anti-isomeric forms and in optical isomeric forms, and that compounds of formula (2) in these isomeric forms are within the scope of the present invention.

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

(III) (II) In the formula, R has the same meaning as described above for formula (I), and X
/ represents halogen or a group -08O1R'(R' is a substituted or unsubstituted alkyl group, phenyl group, or alkoxy group).

In the above method, 2-nitro-5-(substituted pyridyloxy)benzoic acid represented by formula (III) is converted into an acid chloride using, for example, thionyl chloride in a conventional manner, and then, for example, in an organic solvent in the presence of a base. A hydroxamic acid derivative represented by formula (II) can be obtained by reacting with O-substituted hydroxylamines.

In the reaction, the amount of thionyl chloride to be used can be selected and changed as appropriate, and may be, for example, 1 to 10 equivalents relative to the compound represented by formula (III). 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 to be used can be appropriately selected and may be, for example, 1 to 3 equivalents. The amount of the base can also be selected appropriately, for example, 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 tetrahydro7rane and dioxane; one or more organic solvents such as acetone; acetonitrile; dimethylformamide; dimethyl sulfoxide; An example is a mixed solvent of the solvent and water.

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

The thus obtained 〇-substituted-2-nitro-5-(substituted pyridyloxy)benzohydroxymic acid derivative represented by formula (II) and the alkylating agent represented by formula (IV) or CH! The hydroximic acid derivative represented by formula (1) used in the herbicidal composition of the present invention can be produced by reacting Nm in an organic solvent in the presence or absence of a base.

The reaction is carried out on a compound represented by formula (II).
The compound represented by I) or CH,N, for example, 1 to 3
It can be carried out using molar equivalents, preferably 1 to 1.5 molar equivalents, for example, under water cooling or at the reflux temperature of the solvent, preferably at room temperature to around 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; ethers such as diethyl ether, tetrahydrofuran, and dioxane; acetone; acetonitrile: dimethylformamide; dimethyl sulfoxide; Give examples of organic solvents such as and mixed solvents of these solvents and water.

Examples of bases that can be 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 (
IV), for example 1 to 3 equivalents, preferably l-1,
5 equivalents can be used, which is preferred because the reaction can be carried out in good yield. In addition, CHx N z as an alkylating agent
There is no need to use a base when carrying out this reaction.

When the reaction is carried out in a two-phase system, tetramethylammonium bromide, tetrabutylammonium bromide,
A phase transfer catalyst such as a quaternary ammonium salt such as benzyltributylammonium bromide or a quaternary phosphonium such as tetraphenylphosphonium bromide is used, for example, from 1 to 5 Qwt%, preferably from 5 to 30 wt%, based on the compound represented by formula (IV). It can be done by

After completion of the reaction, the compound represented by formula (I) can be isolated by, for example, pouring the reaction mixture into water and treating it according to conventional methods such as extraction with an organic solvent, recrystallization, column chromatography, and the like.

The herbicidal composition of the present invention comprises at least one 2-nitro-5-(substituted pyridyloxy)benzohydroxymic acid derivative of the formula (D) produced as described above, pendimethalin and It contains at least one dinitroaniline derivative selected from trifluralin as an active ingredient.

The blending ratio of the 2-nitro-5-(substituted pyridyloxy)benzohydroxymic acid derivative represented by formula (1) and the dinitroaniline derivative in the composition of the present invention is not strictly limited; The agent composition can be varied over a wide range depending on the application location, application target, application time, etc., but in general, the former 2-nitro-5
- (substituted pyridyloxy)benzohydroxymic acid derivative 1 part by weight, the latter dinitroaniline derivative 0
．． It is appropriate to mix it in a proportion of 5 to 100 parts by weight, preferably 1 to 30 parts by weight, and more preferably 1 to 10 parts by weight.

When the composition of the present invention is actually used as a herbicide, the above-mentioned active ingredients are mixed with known solid or liquid carriers or diluents, surfactants and other formulation auxiliaries by methods known per se. Formulation forms commonly used as agricultural chemicals, such as powders, granules, emulsions, wettable powders, aqueous solutions, etc.
It can be prepared into a 0-tablet formulation, etc.

Solid carriers that can be used include clays such as kaolinite group, montmorillonite group, or attapulgite group, and talc; mica, waxite, pumice, acid clay vermiculite, pyrolite, bentonite, gypsum, calcium carbonate, dolomite, and silica. So soil, calcite,
Inorganic substances such as magnesium lime, apatite, zeolite, anhydrous silicic acid, and synthetic calcium silicate; Vegetable organic substances such as soybean flour, tobacco powder, walnut flour, wheat flour, wood flour, starch, and crystalline cellulose; Coumaron resin, Examples include synthetic or natural polymeric compounds such as petroleum resin, alkyd resin, polyvinyl chloride, polyalkylene glycol, ketone resin, ester gum, copal gum, and dammar gum; waxes such as carnauba wax and beeswax; and urea.

Suitable liquid carriers include, for example, paraffinic or heptene hydrocarbons such as kerosene, mineral oil, spindle oil, white oil; benzene, toluene, xylene,
Aromatic hydrocarbons such as ethylbenzene, cumene, methylnaphthalene; Chlorinated hydrocarbons such as carbon tetrachloride, chloroform, trichloroethylene, monochlorobenzene, 0-chlorotoluene; Ethers such as dioxane and tetrahydrofuran: acetone, methyl ethyl ketone, diisobutyl Ketones such as ketones, cyclohexanone, acetophenone, isophorone; Esters such as ethyl acetate, amyl acetate, ethylene glycol acetate, diethylene glycol acetate, dibutyl maleate, diethyl succinate; methanol n-/\xanol, ethylene glycol, diethylene glycol, Alcohols such as cyclohexanol and benzyl alcohol; ether alcohols such as ethylene glycol ethyl ether and diethylene glycol butyl ether; polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.

In addition, emulsification, dispersion, wetting, spreading, binding of active ingredients,
Surfactants and other auxiliary agents may also be used for the purposes of controlling disintegration, stabilizing active ingredients, improving fluidity, preventing rust, and the like. Examples of surfactants used can be nonionic, anionic, cationic and zwitterionic, but typically nonionic and/or anionic surfactants can be used. things 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; Ethylene oxide is polymerized and added to alkylnaphthols such as butylnaphthol and octylnaphthol; ethylene oxide is polymerized and added to higher fatty acids such as palmitic acid, stearic acid, and oleic acid Ethylene oxide is added to amines such as nidodecylamine and stearic acid amide. Examples include those obtained by polymerizing and adding ethylene oxide; higher fatty acid esters of polyhydric alcohols such as sorbitan and those obtained by polymerizing and adding ethylene oxide; and those obtained by polymerizing and adding ethylene oxide and propylene oxide. Suitable anionic 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; Examples include aryl sulfonates such as sodium isopropylnaphthalene sulfonate, sodium methylene bisnaphthalene sulfonate, sodium lignin sulfonate, and sodium dodecylbenzenesulfonate.

Furthermore, the composition of the present invention contains casein, gelatin, albumin, etc. for the purpose of improving the properties of the preparation and increasing the herbicidal effect.
Do not use polymeric compounds such as glue, lignin sulfonate, alginate, isopropyl acid phosphate (PAP), gum arabic, carboxymethylcellulose, hydroxyethylcellulose, polyvinyl alcohol, polyvinylpyrrolidone, polysaccharide, or other auxiliaries. You can also do it.

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

Powders, for example, usually contain 1 to 25% by weight of the active ingredient, with the remainder being solid carriers, surfactants, and the like.

Wettable powders usually contain, for example, 25 to 90% by weight of the active ingredient, with the remainder being a solid carrier and a dispersing wetting agent, with protective colloid agents, thixotrope agents, antifoaming agents, etc. added as necessary.

Powders, for example, usually contain 1 to 35% by weight of the active ingredient, with the remainder being solid carriers, surfactants, and the like. The active ingredient is uniformly mixed with the solid carrier, or is uniformly fixed or adsorbed on the surface of the solid carrier, and the particle diameter is about 0.2 to 1.5 mm.

Emulsions, for example, usually contain 1 to 30% by weight of the active ingredient, including about 5 to 20% by weight of an emulsifier, the remainder being a liquid carrier, and optionally a spreading agent and a rust inhibitor. is added.

Flowable agents, for example, usually contain 5 to 50% by weight of the active ingredient.
This includes 3 to 10% by weight of a dispersion wetting agent, and the remainder is water, with protective colloids, preservatives, antifoaming agents, etc. added as necessary.

Furthermore, the composition of the present invention can be further mixed with other herbicides, insecticides, fungicides, plant growth regulators, etc. to make it a labor-saving pest control agent.

The herbicide composition of the present invention is effective for controlling a wide range of weeds in agricultural land or non-agricultural land, especially in upland fields, and is particularly useful for controlling major weeds in cereal crops.

Therefore, the herbicide composition of the present invention can be applied to, for example, Veronica persica, Veronica hedarifolia, and Veronica hedarifolia.
), Chickweed (S telIaria media)
, Lamium purpureu
+++), Hotokenoza (Lamium amplex)
icaule), Yaemugura (Galium apar)
ine), Matricaria m.
atricarioides), chamomile (Matr
+caria chamomilla), Anthemis cotula, Papavsr rhoeas, Cirsium arvense, Spergula arvensis , CerasLium vulgatuFl
, Arenaria 5erpylli
folia), Silene vul
garis), Erysimum ch.
eiranthoides), Miner's lettuce (M
ontia perfoliata), Anagallis arvensis, Forget-me-not (MyO3OLIS arVensls)
, Chenopod iumalbum ,
Polygonum aviculare
), Polygonum convolv.
ulus), corn marigold (Chrysan
themum segetum), briefstone (Aphanes arvensis), chamomile weed (Matricaria 1nodora), chamomile weed (Anthamis arvens)
is), looking grass weed (Legousia
hybrida), American flaxweed (Gera
nium moils), 70 American weeds (Ge
ranium dissectum), frixweed (Descurainea 5ophia),
Common hemp nettle (Galeopsis tetr)
ahit), Poaannua
, oat (Avena fatua), star wheat (Lolium perenne), rat wheat (
Lolium multiflorum), strawberry weed (Poa 5phondylodes), sparrowweed (Alopecurus myosur)
oides), rose silk event (Apera 5
pica-venti), Pha
laris paradoxa), Phalaris m1nor, oat weed (Avena ludoviciana), oat weed (Bromus 5terilis)
etc. can be effectively controlled by treatment (soil treatment) before the weeds emerge. The composition of the present invention usually comprises wheat, barley,
It is particularly suitable for selective weeding in fields where wheat such as oats grows, but it is also suitable for selective weeding in agricultural lands where rice, corn, sugarcane, soybeans, cotton, sunflowers, etc. grow. It can be used for. Furthermore, good results can be obtained when applied to fields such as lawns, orchards, forest nurseries, and non-agricultural lands.

Although the appropriate application amount of the composition of the present invention cannot be determined unconditionally due to differences in weather conditions, soil conditions, drug formulation, target crops, application timing, application method, etc., it is usually based on the total amount of active ingredients. A suitable range is 0.1-10 kg, preferably 0.2-41 (g) per hectare.

Next, the present invention will be explained in more detail with reference to production examples, working examples, and test examples.

Manufacturing example 1. [Methyl 0-methoxycarbonyl methyl
Preparation of 5-(3-chloro-5-trifluoromethyl-2-pyridyloxy)-2-nitropenzohydrooximate (compound No. 1) 15-(3-chloro-5-trifluoromethyl-2-pyridyloxy) )-2-nitrobenzoic acid (36°2 g (0.10 mol)) and thionyl chloride (36°)
．． Dissolve to 2mM and heat under reflux for 1.5 hours. Excess thionyl chloride is distilled off to obtain acid chloride.

Aminooxyacetic acid methyl ester io, 5g (0.1%
), trixtyl7mine 10.1g (0.1 mol),
To a solution of 300 mQ of dry ether, while stirring under water cooling, the solution of the acid chloride obtained previously in 150 rtQ of ether is added dropwise over about 20 minutes. After that, 30 minutes under water cooling, 1.5 minutes at room temperature.
Stir for an hour. The reaction solution was poured into 30C1+Q ice water, extracted three times with ethyl acetate 200+uff, washed with saturated brine, and dried over magnesium sulfate. After filtering out the desiccant,
The solid obtained by distilling off the solvent was recrystallized from toluene,
37.2 g of methoxycarbonylmethyl 5-(310rho-5-trifluoromethyl-2-pyridyloxy)-2nitrobenzohydroxamate was obtained (yield: 82.7%).
).

37.2 g of the hydroxamate obtained above was dissolved in a mixed solvent of ether 707M (1, tetrahydrofuran'1, OraQ), and under water cooling and stirring, N-nitrone methyl urea
A solution of 300 ml (l) of diazomethane prepared from 4.8 g (0,241 mol) in ether is added dropwise over about 40 minutes.Then, the mixture is stirred under water cooling for about 30 minutes.Excess diazomethane is decomposed with acetic acid, and the solvent is removed. The solid obtained was recrystallized from methanol to obtain the target compound No.
syn type)? : (27.0g, yield 70.4%),
mp, 71° 0-73.0° 5.0 g of the above compound No. 1 was added to toluene 200 rx (
After dissolving the solution in 100 ml of water and deaerating it by bubbling N2, it was irradiated with light for 3 hours using a high-pressure mercury lamp (Rikou Kagaku Sangyo UVL-1009). The solvent was distilled off and the residue was purified by column chromatography (silica gel-N-hexane-5-7-acetic acid 2:1) to obtain the target compound No. 1 isomer (anti type) (3.5 gs Yield 70.0%, mp, 84.5-85.
5°).

By the same method as in the above production example, the 2-nid 0-
5-(substituted pyridyloxy)benzohydroxymic acid derivatives can be produced.

Table-1 Js 3 n-C3H.

4 1so-CsHt 5 n-C, H.

mp, 84.5-85.5°C (anti) mp, 101
．． 5=103.0℃(syn)mp, 58.0=59-
5℃(anti)o+p, 71.5-73.1℃(an
ti)mp, 97. ! r99.0℃(anti)mp,
84.0-85.0°C (anti) Example 1 (emulsion) Compound No. 25 parts by weight Pendimethalin 25 parts by weight Polyoxyethylene styrylphenyl ether 101% by weight Xylene 60 parts by weight or more of each component were uniformly mixed. Dissolve to obtain an emulsion.

Example 2 (Emulsion) Compound NO, 25 parts by weight Trifluralin 25 parts by weight Polyoxyethylene styrylphenyl ether 10 parts by weight Xylene 60 parts by weight or more are uniformly mixed and dissolved to obtain an emulsion.

Example 3 (Wettable powder) Compound No. 1 8 parts by weight Pendimethalin 40 parts by weight Sodium lauryl sulfate 4 parts by weight Talc 42 parts by weight or more of each component is mixed and pulverized in a Nigu to obtain a wettable powder.

Example 4 (70 Able Agent) Compound No. 3 100 parts by weight Trifluralin 40 parts by weight Polyoxyethylene sorbitan monooleate 3 parts by weight Water
45 parts by weight or more of each component are mixed and uniformly ground and mixed in a wet ball mill until the particle size becomes 5 microns or less to obtain 70 apples.

Test Example 1 (Soil treatment test) A square pot measuring 30 cm x 30 cm x 9 cm (depth) was filled with field soil, and fixed amounts of each crop seed and weed seed shown in Table 2 below were sown, and the pot was covered with soil to a thickness of 1 cm. .

For the chemical treatment, emulsions of compounds No., 'l, pendimethalin, and trifluralin were prepared, diluted with water to the amounts of each active ingredient shown in Table 2, and uniformly spread on the soil surface.

On the 28th day after the chemical treatment, the herbicidal effect on each weed and the degree of phytotoxicity of each crop were determined according to the evaluation criteria below, and the results are shown in Table 2.

Evaluation criteria evaluation value Herbicidal effect (%) Degree of chemical damage (%) 0 Weed suppression rate θ
~9 Drug damage damage rate O~91 10~19
10-19220-2920-29 330-3930-39 440-4940-49 550-5950-59 6 60-6960-69 770-7970-79 880-8980-89 990-9990-99 10 100 to.

Test Example 2 (Field Test) In a field where chickweed, cypressweed, and sparrowweed were abundant, 120 kg of wheat seeds (Norin No. 61) and chemical fertilizer (Kumiai Rinkaan No. 4) were applied per hectare.
The whole layer was mixed and then divided into test sections of 2 m x 5 m.

In the drug treatment, the emulsion of Example 1, the emulsion of Example 2, and the compound N 0.2% pendimethalin and trifluralin emulsions were mixed at 500 mg per section so as to have the respective active ingredient amounts shown in Table 3. It was diluted with water and spread evenly over the soil surface.

On the 40th day after the chemical treatment, the herbicidal effect on each weed and the degree of chemical damage to wheat were determined according to the evaluation criteria described above, and the results are shown in Table 3 below.

The emulsions used in Test Examples 1 and 2 above were those of Example 1.
Or, according to 2, 10 parts by weight of polyoxyethylene styrylphenyl ether was added to the predetermined amount of each test drug, the total amount was adjusted to 100 parts by weight with xylene, and the mixture was thoroughly mixed and dissolved.

Claims (1)

[Claims] (a) General formula (I) ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (I) In the formula, R represents a lower alkyl group, 2-nitro-5-(substituted (b) 3,4-dimethyl-2,6-dinitro-N-1-
Ethylpropylaniline and 2,6-dinitro-N,N
A herbicidal composition comprising at least one dinitroaniline derivative selected from -dipropyl-4-trifluoromethylaniline as an active ingredient.