DD145050A5 - HERBICIDE MEDIUM - Google Patents

Abstract

1. A herbicidal agent for the selective control of unwanted plant growth in Indian corn, characterized in that it contains a substituted acetanilide of the formula I see diagramm : EP0009091,P5,F1 where R denotes methyl or ethyl, R**1 denotes methyl or ethyl, and A denotes a pyrazole radical which may be substituted by methyl groups in the 3- and 5-positions and which is attached via a ring nitrogen atom, as herbicidal active ingredient and N-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine as antagonistic agent.

Description

The new herbicidal agents can be used in agriculture to control undesired plant growth.

Characteristic of the known technical solutions Substituted acetanilides of the formula I 10

CO-CH ₂ -X η η

15 in the

R is hydrogen, an unbranched or branched alkyl or alkoxy radical having up to 5 carbon atoms, R is hydrogen, halogen, an unbranched or branched; R 1 is hydrogen, halogen, an unbranched or branched alkyl or alkoxy radical having up to 5 carbon atoms,

R together with R denotes an ortho-linked _s- alkylene chain optionally substituted by unbranched or branched alkyl groups having up to k carbon atoms

25 to 6 carbon atoms, H / Br

ξ%

2 - 0.2. ΟΟ5Ο / Ο33324

¹ X chlorine or bromine and. '

A is an azole bonded via a ring nitrogen atom, which is mono- or polysubstituted by halogen, phenyl, alkyl, alkoxy, alkylthio or perfluoroalkyl radicals each having up to 4 carbon atoms, cyano, carboxy, carbalkoxy having up to 4 carbon atoms in the alkoxy group or alkanoyl radicals where A may also be substituted by salts of azoles containing 2 or 3 nitrogen atoms, herbicides are excellently effective, but when used in crops such as maize or in cultures of the graminaceous family Damage to crops.

Herbicidal agents which contain, in addition to chloroacetanilides as herbicidal active ingredients, antagonistic dichloroacetamides, are known from US Pat. No. 4,053,297, DE-OS No. 2,218,097 and DE-OS '24 02 983. Among others, dichloroacetamides are mentioned in these documents as possible antidotes, in which the two substituents on the nitrogen atom together with this form a heterocyclic ring which may contain another heteroatom and may be substituted by alkyl groups. As representatives of this class of compounds, inter alia N-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine is mentioned.

,

In DE-OS 22 18 097, however, this antagonistic compound is only recommended in combination with herbicidally active thiolcarbamates, while it is known from DE-OS 24 02 and US Pat. No. 4,053,297 that N-dichloroacetyl-2 _s 2 ~ dimethyl-1,3-oxazolidine is useful as an antidote to reduce Mai-s damage when using herbicidal chloroacetanilides. The chloroacetanilides used here carry am-nitrogen in addition to the chloroacetyl substituted alkyl, alkoxyalkyl, Alkenyloxyalkyl- or Cycloalkyloxyalkylreste or

- 3 - O.Z. ÖO5O / O33324

a methylene group bonded, 'oxygen and / or sulfur-containing saturated rings.

Object of the invention

The aim of the invention was therefore to find antagonistic agents that compensate for this incompatibility of the herbicidal acetanilides against certain crops.

10 Presentation of the essence of the invention

It has been found that N-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine is suitable for increasing the crop plant compatibility of the herbicidally substituted acetanilides of the formula I. Herbicidal agents containing at least one substituted acetanilide of the formula I and N-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine can be used without difficulty in maize. In this case, the good herbicidal action of the acetanilides is maintained, while damage to the crops are prevented.

Acetanilides whose crop plant compatibility can be improved by N-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine are those in which R is hydrogen, alkyl of up to 5 carbon atoms, such as methyl, Ä'thyl, n-propyl, i Propyl, η-butyl, sec-butyl, i-butyl, tert-butyl, normal and branched pentyl, alkoxy of up to 5 carbon atoms, such as methoxy, ethoxy, propoxy, butoxy, pentyloxy; ,

12

R and R. is hydrogen, halogen, such as fluorine, chlorine, bromine or iodine, alkyl having up to 5 carbon atoms, such as methyl, ethyl, n-propyl, i-propyl, η-butyl, sec-butyl, i-butyl, tert-butyl , n-pentyl and branched pentyl, alkoxy of up to 5 carbon atoms, methoxy, ethoxy, propoxy, butoxy, pentyloxy;

- 4 - O.Z, OO5O / O33324

'' R linked together with R is an ortho, gegebe- ¹ appropriate, by alkyl having up to 4 carbon atoms substituted alkylene chain having up to 6 carbon atoms, such as ethylene, trimethylene, tetramethylene, 1-methyl-trimethylene, I ₃ l-dimethyl-trimethylene , 1,1-dimethyl-tetraraethylene; '

X is chlorine or bromine, preferably chlorine and A is an azole bonded via a ring nitrogen atom, such as pyrrole, pyrazole, iridazole, 1,2,4-triazole, 1,2,3-triazole, tetrazole, which is mono- or polysubstituted. by halogen, phenyl, alkyl ', alkoxy, alkylthio or perfluoroalkyl radicals each having up to 4 carbon atoms, cyano, carboxy, Carbalkoxyreste having up to 4 carbon atoms in the alkoxy group or alkanoyl having up to 4 carbon atoms may be independently substituted, such as 2,6-dimethylpyrrole, tetramethylpyrrole, 3 (5) -methylpyrazole, 4-methylpyrazole, 3 (5) -ethylpyrazole, 4-ethylpyrazole, 3 (5) -isopropylphenylazole, 4-isopropylpyrrole, 3, 5 -Dimethylpyrazol, 3-dimethyl-5 _s ⁱ i-acetylpyrazol, 3,5-dimethyl-4-propionylpyrazol, 3> 4,5-trimethylpyrazole, 3 (5) -Phenylpyrazol, 4-phenylpyrazole, 3,5-diphenylpyrazole, 3 (5) -phenyl-5 (3) -methylpyrazole, 3 (5) -chloropyrazole, 4-chloropyrazole, 4-bromopyrazole, 4-iodopyrazole, 3,4,5- "trichloropyrazole, 3> 4,5-tribromopyrazole , 3 _s 5-dimethyl-4-chloropyr azole, 3,5-dimethyl-4-bromopyrazole, 4-chloro-3 (5) -methylpyrazole, _s- 4-bromo-3 (5) -methylpyrazole, 4-methyl-3> 5-dichloropyrazole, 3 (5) -methyl -4.5 (3) - * dichloropyrazole, 3 (5) -chloro-5 (3) -methylpyrazole, 4-methoxypyrazole, .3 (5) -methyl-5 (3) -methoxypyrazole, 3 (5) -ethoxy -4,5 (3) -dimethylpyrazole, 3 (5) -methyl-5 (3) -trifluoromethylpyrazole, 3,5-bistrifluoromethylpyrazole, 3 (5) -methyl-5 (3) -carbethoxypyrazole, 3.5 ~ Biscarbethoxypyrazole, 3,4,5-triscarbethoxypyrazole, 3 (5) -methyl-5 (3) -methylthio-4-carbethoxypyrazole, 4-methyl-3, 5-biscarbethoxypyrazole, 4-cyanopyrazole, 4-hethoxy-3,5 " dichloropyrazole, 4,5-dichloro-imidazole, 2-ethyl

- 5 - ° · ^ζ · ΟΟ5Ο / Ο33324

"4", 5-dichloro-imidazole, 2-methyl-4,5-dichloroimidazole, 3 (5) -methyl-1, 2,4-triazole, 3,5-dimethyl-1,4-triazole, 3 (5) Chloro-1, 2,4-triazole, 3 (5) -bromo-1, 2,4-triazole, 3 (5) -. , Chloro-5 (3 ') - methyl-l, 2,4-triazole, 3,5-dichloro-l, 2,4-triazole, 3,5-dibromo-l, 2,4-triazole, 3 (5) -chloro-5 (3) -eyano-l, 2,4-triazole, 3 (5) -chloro-5 (3) -phenyl-l, 2,4-triazole, 3 (5) -chloro \ 5 ( 3) -carbomethoxy-l, 2,4-triazole, 3 (5) -methylthio-l, 2,4-triazole, 4 (5) -methyl-l, 2,3-triazole, 4,5-dimethyl-l ₅ 2 _s 3-triazole 4 (5) -phenyl-l, 2,3-triazole, 4 (5) -chloro-1, 2,3-triazole, 1,2,3-trlazol *! (5) -yl-carboxylic acid ethyl ester, 1,2,3-triazol-4,5-yl-dicarboxylic acid dimethyl ester, 5-methyltetrazole, 5-chlorotetrazole, tetrazolyl-5-carbonsaureathylester stands.

In addition, the radical A, if the optionally substituted azole contains 2 or 3 nitrogen atoms, also salt-like to one of the usual strong inorganic or organic acids such as hydrochloric acid, bromine water. acid, nitric acid, sulfuric acid, tetrafluoroboric acid, fluorosulfonic acid, formic acid, a halogenated carboxylic acid, e.g. Trichloroacetic acid, an alkanesulfonic acid, e.g. Methanesulfonic acid, a halogenated alkanesulfonic acid, e.g. Trifluoromethanesulfonic acid, perfluorohexanesulfonic acid, an arylsulfonic acid, e.g. Dodecylbenzenesulfonic acid, be bound.

Preference is given to acetanilides which carry methyl, ethyl or ethyl in the 2- and 6-position on the phenyl ring and hydrogen, methyl or ethyl in the 3-position, azrazoles being pyrazole, imidazole, triazole or tetrazole, each being represented by lower alkyl, alkoxy, carbalkoxy , Cyan or halogen may be substituted come into consideration.

- β - 0.2. 0050/033324

In particular, the herbicidal ^{agents according to} the invention contain the following acetanilides:

2-Chloro-2 ', 6'-dimethyl-N-pyrazol-1-yl-methyl) -acetanilide, 2-chloro-2'-methyl-6'-ethyl-N- (pyrazol-1-yl-methyl) acetanilide, 2-chloro- ^2f , 6'-dimethyl-N- (4-methylpyrazol-1-yl-methyl) -acetanilide, 2-chloro-2'-methyl-6'-ethyl-N- (4- methoxypyrazol-1-ylmethyl) -acetanilide, 2-chloro-2 ', methyl-6'-ethyl-N- (3 (5) -methylpyrazol-1-yl) -acetanilide, 2-chloro-2', 6'-dimethyl-N- (3,5-dimethylpyrazol-1-ylmethyl) -acetanilide, 2-chloro-2 ', 6'-dimethyl-N- (1,2, U -triazol-1-ylmethyl ) -acetanilide, 2-chloro-2 ', 6'-dimethyl-N- (4-chloropyrazol-1-ylmethyl) -acetanilide, 2-chloro-2', 3 ', 6'-trimethyl-N- ( pyrazol-1-ylmethyl) -acetanilide, 2-chloro-2'-methyl-6'-ethyl-N- (3,5-dimethyl-pyrazol-1-ylmethyl) -acstanilide, 2-chloro -2 ', 6'-diethyl-N- (3,5-dimethyl-pyrazol-1-yl-methyl) -acetanilide, 2-chloro-2', 3 ', 6'-trimethyl-N- (3 _s 5 -dimethylpyrazol-1-ylmethyl) -acetanilide, 2-chloro- ^2f , 6'-diethyl-N- (4-methylpyrazol-1-ylmethyl) -acetanilide, 2-chloro-2'-methyl -6'-ethyl-N- (4-methylpyrazol-1-ylmethyl) -acetanilide, 2-chloro-2 ', 3', 6 '-trimethyl-N- (4-ethylpyrazol-1-yl-methyl) -acetanilide, 2-chloro-2''',6'-dimethyl-N- (3- (5) -methylpyrazole-. 1-yl-methyl) -acetanilide, 2-chloro-2 ', 6'-diethyl-N- (3- (5) -methylpyrazol-1-yl-methyl) -acetanilide, 2-chloro-2' , 6 '-dimethyl-N- (4-methoxypyrazol-1-ylmethyl) -acetanilide, 2-chloro-2', 6'-diethyl-N- (pyrazol-1-ylmethyl) -acetanilide, 2- Chloro-2 ¹ , 6'-dimethyl-N- (4,5-di-chloroimidazol-1-yl-methyl) -acetanilide,. 2-chloro-2. ^! -methyl-6'-ethyl-N- (4,5-dichloro-imidazol-1-ylmethyl) -acetanilide, 2-chloro-2 ', 6'-diethyl-N- (4,5-dichloroimidazol-1-yl -methyl) -acetanilide, 2-chloro-2'-methyl-6'-ethyl-N- (2-ethyl-4,5-dichloroimidazol-1-ylmethyl) -acetanilide, 2-chloro-2- ^t- methyl -6'-ethyl-N- (l _i 2 _s 4-triazol-l-ylmethyD-acetanilide, ', 6 ^l -diäthyl-N. - (l, 2, 4-tri-' 2-chloro-2 azpl- 1-yl-methyl) -acetanilide and 2-chloro-2 ', 3', 6'-trimethyl-N- (1,2,4-triazol-1-yl-methyl) -acetanilide.

o.z. 0050/033324

^r A particularly preferred composition of this invention contains N-dichloroacetyl-2,2-diraethyl-l, 3 "" oxazolidine 2-chloro-2 ^f j6 ^I -dimethyl-N- (l-pyra.zoi-yl-methyl) -acetanilide as herbicidal active ingredient.

The acetanilides of the formula I are the subject of DE-OS 26 48 008 and DE-OS 27 44 396. They can be prepared by reacting 2-halo-N-halomethyl-acetanilides of the formula II with an 1H-azole of the formula HA The following reaction equation gives four:

HA

CO-CH ₂ -X

+ HX

CO-CH ₂ -X

1 2 Here, the substituents, R, R, R and X have the above. and A is an azole bonded via a ring nitrogen atom, which is monosubstituted or polysubstituted by halogen, phenyl, alkyl, alkoxy, alkylthio or perfluoroalkyl radicals each having up to 4 carbon atoms, cyano, carboxy, carbalkoxy radicals having up to 4 Carbon atoms in the alkoxy group or alkanoyl radicals having up to 4 carbon atoms may be substituted. , ,

The preparation of N ~ dichloroacetyl-2,2-dimethyl-l, 3 ~ oxazole idin is described in DE-OS 22 18 097 and DE-OS 24 02 983.

N-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine itself has little or no visible influence on germination and growth of both crops and unwanted plants, even at rates which are considerable

- P, _ Λ 7 Γ; ^ = ^ / pi "^" ^ "CIi.

- ο - U. £ ο <^> ^ / 0 >>> <i.

above those needed to achieve an anti ^- gonistic effect. However, they have the ability to significantly reduce or completely eliminate the phytotoxicity of the herbicidal acetanilides of the formula to crops such as corn.

For herbicidal acetanilides which are less aggressive towards the crops, minor additions of N-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine suffice. The proportion acetanilide: N ~ dichloroacetyl-2,2-dimethyl-l, 3-oxazolidine can vary widely; it depends on the acetanilide. Suitable ratios of herbicidal active ingredient: N-dichloroacetyl-2,2-dimethyl-l, 3-oxazolidine are between 1: 2 to 1: 0.01 parts by weight.

Acetanilide and antagonist may be incorporated into the soil together or separately, before or after sowing. For the acetanilides of the formula I, the most common method of application is the application to the surface of the earth immediately after deposition of the seeds or in the time between sowing and emergence of the young plants. Also treatment during emergence and shortly thereafter is possible. In any case, the antagonistic compound can be applied simultaneously with the herbicidal active ingredient. Also, a separate application, wherein the antagonist are placed first and then the herbicide or vice versa on the field is possible, unless in the latter case, not so much time elapses that the herbicide has already done damage to the crop. Herbicide and antagonist may be present as sprays in suspendable, emulsifiable or soluble form or as granules, separately or jointly formulated. It is also conceivable to treat the crop seeds with the antagonist before sowing. The herbicide is then applied alone in the usual way.

- 9 - 0.2.

In addition to acetanilide and antagonist, the ^novel herbicidal compositions may ^contain further herbicidal or growth-regulating active ingredients of a different chemical structure, for example 2-chloro-ethyl-6-isopropylamino-1,3,5-triazine, without the antagonistic effect of N-dichloroacetyl-2,2-dimethyl-l, 3-oxazolidine is affected.

The compositions according to the invention or, when applied separately, the herbicidal active compounds or the antidote are used, for example, in the form of directly sprayable solutions, powders, suspensions, even high-percentage aqueous, oily or other suspensions, or dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents or granules applied by spraying, atomizing, dusting, scattering or pouring. The forms of application depend entirely on the intended use; In any case, they should ensure as far as possible the finest distribution of the compositions or individual components according to the invention. , ·

For the production of directly sprayable solutions, emulsions, pastes and oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, coal tar oils, and oils of vegetable or animal origin, aliphatic, cyclic or aromatic hydrocarbons, for example benzene, toluene, xylene, Paraffin, Tetrahydronaphthaiin, alkylated naphthalenes or derivatives thereof, for example, methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, strongly polar solvents, such as Dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, V / asser, into consideration.

Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders), oil-dispersed

0 7 ρ ^ - ^ Λ, / ρ ^ ^. ^ ρ Ii

sionsn be prepared by the addition of water. For the preparation of emulsions, pastes or oil dispersions herbicidal active ingredient and / or antidote can be dissolved as such or in an oil or solvent, · homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers. But it can also be prepared from herbicidal active ingredient and / or Antidot.Netz-, adhesive, dispersing or emulsifying and possibly solvent, or oil concentrates, which are suitable for dilution with water.

Suitable surface-active substances are: alkali metal, alkaline earth metal, ammonium salts of ligninsulfonic, naphthalenesulfonic, phenolsulfonic, alkylarylsulfonates, alkylsulfates, alkylsulfonates, alkali metal and alkaline earth metal salts of dibutylnaphthalenesulfonic acid, lauryl ether sulfate, fatty alcohol sulfates, fatty alkali and alkaline earth salts, salts of sulfated hexadecanols, heptadecanols , and octadecanols, salts of sulfated fatty alcohol glycol ethers, condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, Polyoxyätfyylenoctylphenoläther, ethoxylated Isooctylphenol-, octylphenol, Npnylphenol, Alkylphenolpolirglykoläther, Tributylphenylpolyglykoläther, .Alkalarylpolyätheralkohole, isotridecyl alcohol, Fettalkoholäthylenoxid- Condensates, ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene _? Laurylalkoholpolyglykolätheracetal, sorbitol esters, lignin, liquors and

30 methyl cellulose.

Powders, litter and dusts may be prepared by mixing or co-grinding herbicidal active ingredient and / or antidote with a solid carrier.

35 *. ~

Alles

- ιι · - OZ CC50 / C33324-

Granules, e.g. Envelope, impregnation and homogenous granules can be prepared by binding the active ingredients to solid carriers. Solid carriers are z.3. Mineral earths such as silica gel, silicic acids, silica gels, silicates, talc, kaolin, attaclay, limestone, chalk, talc, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulphate, magnesium oxide, ground plastics, fertilizers, e.g. Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.

The formulations contain between 0.1 and 95% by weight of herbicidal active ingredient and antidote, preferably between 0.5 and 90% by weight. The application rates of herbicidal active ingredient are from 0.2 to 5 kg / ha. This amount of herbicidal active ingredient is applied, jointly or separately, with an amount of antidote such that the proportion of herbicidal active ingredient: antagonistic compound

is 1: 2 to 1: 0.01 parts by weight.

Examples of formulations are:

I. 40 parts by weight of the mixture of four parts by weight of 2-chloro-2 ', 6'-dimethyl-N ~ (pyrasol-1-ylmethyl) -acetamide and one part by weight of N-dichloroacetyl-2,2-dimethyl l, 3-oxazolidin are mixed with 10 parts of sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts of silica gel and 48 parts v / ater intimately ³ ^. A stable aqueous dispersion is obtained. Dilution with 100,000 parts by weight of water gives an aqueous dispersion which contains 0.04% by weight of active compound.

- 12 - 0 2 o ~ ^ / r> - ^ - Z-Oh.

3 parts by weight of the mixture of one part by weight; 2-chloro-2 ^T, 6 '-dimethyl -N- * (pyrazol-1-yl-methyl) -acetanilide and one part by weight N-Dichlcracetyl _i-2, 2-dimethyl-1,3-oxazolidine with 97 parts by weight of finely divided' Kaolin intimately mixed. This gives a dust containing 3% by weight of the active ingredient.

III. 30 weight steep ε the mixture of one part by weight of 2-chloro-2 ^l -methyl-6'-ethyl-N- (l, 2, ¹ 4-triazol-l-yl-methyl) -acetanilid and two weight steep N- Di-chloroacetyl-2,2-dimethyl-1,3-oxazolidine are intimately mixed with a mixture of 92 parts by weight of powdered silica gel and 3 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel. This gives a preparation of the active ingredient with good adhesion.

IV. 20 parts of the mixture of eight parts by weight of 2-chloro-2'-methyl-β'-ethyl-N- (pyrazol-1-yl-methyl) -acetanilide and one part by weight of N-dichloroacetyl-2,2-dimethyl- ^:; -l, 3-oxazolidine are mixed with 2 parts of calcium dodecylbenzenesulfonate, 8 parts of fatty alcohol poly- • 25 glycol ether, 2 parts of sodium salt of a phenolsulfone

acid-urea-formaldehyde condensate and 68 parts of a paraffinic mineral oil intimately mixed. This gives a stable oily dispersion.

V. 20 parts by weight of the mixture of ten parts by weight of 2-chloro-2 ', ^6f -dimethyl-N- (4,5-dichloro-imidazol-1-yl-methyl) -acetanilide and one part by weight of N-dichloro-acetyl-2, 2-dimethyl-l-oxazolidin _s 3 are dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of arrival

- i> -. O. Z. 005C / C33324

Storage product of 7 moles of ethylene oxide to 1 McI Isc * ¹ octylphenol and 10 parts by weight of the adduct before, 40 moles of ethylene oxide to 1 mole of castor oil. By pouring and finely distributing the solution in 100,000 parts by weight of water to obtain an aqueous dispersion containing 0.02 weight percent of the active ingredient.

Exemplary embodiments

Greenhouse experiments show that when using the herbicidal compositions of the invention, the compatibility of the herbicidal acetanilides is increased for the crop without the herbicidal activity is reduced.

In this case, plastic pits of 51 cm length, 32 cm width and 6 cm height were filled with loamy sand or sandy loam of pH 6 to 7 and about 1.5 $ of humus. In this substrate corn (Zeamays) was sown flat as a crop in rows. In addition, millet (Echinochloa. Crus galli) was added as an undesirable plant. The non-sterilized soil additionally contained viable weed seeds, which contributed to the population of undesirable plants. This simulated crop-planted and weed-infested fields.

- ';' ·

The active ingredients and the antagonistic compound were applied both individually and in the described mixtures. They were, emulsified or suspended in water as the carrier medium, sprayed by means of finely distributing nozzles immediately after sowing and before emergence of the test plants on the earth's surface. After sowing and treatment, the boxes are watered and covered with transparent plastic hoods until after planting. By this measure, a uniform germination and growth of the plants was guaranteed. The installation took place

In a temperature range from an average of 18 to 3O ⁰ C. The so-scale greenhouse experiments were monitored until May's had developed 3 to 5 leaves,

The mean exposure was rated on a scale from 0 to. Here, 0 means normal rise and normal development of the plants relative to the untreated control. 100 corresponds to a total absence of germination or death of the plants. It had to be considered that e.g. in maize even under completely normal conditions and without any chemical treatment occasionally crippled or inhibited plants occur.

The following table shows the extent to which N-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine is compatible with acetanilides of the formula I, for example 2-chloro- 2 ', 6'-dinefhyl-N-cpyrazole-1 -yl-methyl) -acetanilide, in

Corn boosts.

35

PO

N>

(Jl

'Table - Improvement of Maize tolerability of 2-chloro-2 _·? 6 '-dimethyl-N-cpyrazol-1-yl-methyl) -acetanilide by N-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine in a pre-emergence application in the greenhouse

Herbicidal active ingredient

Antagonistic compound

Application rate of test plants and damage Qcg / ha a.S.J Zea mays Echinochloa

crus galli

CO-CH ₂ Cl

1.0

2.0

6H 99 t 79 99

0 Cl ₂ Cli-CN

HC

1.0 + 0.25 1.0 + 2.0

2.0 + 0.5 2.0 + 2.0

15 10 1 * 1 10

98

98

99

100

0 = normal rise, no damage = plants did not accumulate or died

Claims (2)

A herbicide containing a solid or liquid carrier and 0.1 to 95 wt -.% Of a mixture of a substituted acetanilide of the formula I , -CO-CK ₀ -X in the R is hydrogen, an unbranched or branched alkyl or alkoxy radical having up to 5 carbon atoms, R hydrogen, halogen, an unbranched or branched alkyl or alkoxy radical having up to 5 carbon atoms, R is hydrogen, halogen, an unbranched or branched alkyl or alkoxy radical having up to 5 carbon atoms, 2
R together with R denotes an alkylene chain having up to 6 carbon atoms which is linked ortho-connected and optionally substituted by unbranched or branched alkyl groups having up to 4 carbon atoms,
X is chlorine or bromine and
A is an azole bonded via a ring nitrogen atom and is monosubstituted or polysubstituted by halogen, phenyl, alkyl, alkoxy, alkylthio or perfluoroalkyl radicals each having up to 4 carbon atoms, cyano, carboxy, carbalkoxy with bis. to 4 carbon atoms in the alkoxy group or alkanoyl radicals having up to 4 carbon atoms may be substituted, where A may also be salts of 2 or 3 nitrogen atoms-containing azoles, as herbicidal active ingredient and N-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine as antagonist agent. , -ν η ί \ · .Γ IQ 7 Q %>