Herbicidal agents based on N-azolylmethylacetanilides and cyclohexane-1,3-dione derivatives

Herbicidal agents containing an N-azolylmethylhaloacetanilide of the formula ##STR1## where R, R.sup.1, R.sup.2, A and X have the meanings given in the disclosure, and a substituted cyclohexane-1,3-dione derivative of the formula ##STR2## where R.sup.1, R.sup.2, R.sup.3, R.sup.4, X and n have the meanings given in the disclosure, or a metal salt or ammonium salt of this cyclohexane-1,3-dione derivative. The ratio of N-azolylmethylhaloacetanilide of the formula I to cyclohexane-1,3-dione derivative of the formula II is from 1:0.125 to 1:10 parts by weight. The agents are suitable for combating unwanted grassy plants.

The present invention relates to herbicidal agents containing mixtures of 
N-azolylmethylacetanilides and cyclohexane-1,3-dione derivatives, and 
processes for controlling unwanted plant growth with these agents. 
The haloacetanilides, which are disclosed in German Laid-Open Application 
DE-OS No. 2,648,008 and bear a substituted or unsubstituted azolylmethyl 
radical which is attached to the nitrogen via a ring nitrogen atom, such 
as pyrazol-1-yl-methyl, triazol-1-yl-methyl or tetrazol-1-yl-methyl, have 
an excellent herbicidal action on grasses at low application rates. 
Further, haloacetanilides having an action on grasses have been disclosed 
in which the azolylmethyl radical is imidazol-1-yl-methyl (German 
Laid-Open Applications DE-OS Nos. 2,704,281 and 2,744,396). 
It has also been disclosed that cyclohexane-1,3-dione derivatives are 
particularly effective for combating grassy plants, and are preferably 
used postemergence (German Laid-Open Application DE-OS No. 2,822,304). 
We have found that herbicidal agents containing a mixture of 
N-azolylmethylhaloacetanilides of the formula 
##STR3## 
where R denotes hydrogen, linear or branched alkyl or alkoxy of a maximum 
of 5 carbon atoms, R.sup.1 and R.sup.2 are identical or different and each 
denotes hydrogen, halogen, or linear or branched alkyl or alkoxy of a 
maximum of 5 carbon atoms, R and R.sup.2 together denote an ortho-position 
alkylene chain of a maximum of 6 carbon atoms which is unsubstituted or 
substituted by linear alkyl of a maximum of 4 carbon atoms, X denotes 
chlorine or bromine, and A denotes azole attached via a ring nitrogen atom 
and which is unsubstituted or mono- or polysubstituted by halogen, phenyl, 
alkyl, alkoxy, alkylthio or perfluoroalkyl, each of a maximum of 4 carbon 
atoms, cyano, carboxy, carbalkoxy, where alkoxy is of a maximum of 4 
carbon atoms, or alkanoyl of a maximum of 4 carbon atoms, or A denotes a 
salt of an azole containing 2 or 3 nitrogen atoms, and substituted 
cyclohexane-1,3-dione derivatives of the formula 
##STR4## 
where R.sup.1 denotes alkyl of a maximum of 4 carbon atoms, phenyl, or 
phenyl or benzyl substituted by halogen, alkyl or alkoxy of a maximum of 4 
carbon atoms, R.sup.2 denotes alkyl of a maximum of 4 carbon atoms, 
R.sup.3 denotes alkyl or alkenyl of a maximum of 4 carbon atoms, R.sup.4 
denotes hydrogen or alkoxycarbonyl of a maximum of 5 carbon atoms, X 
denotes linear or branched alkylene of a maximum of 4 carbon atoms, and n 
denotes one of the integers 0, 1 and 2, or metal salts or ammonium salts 
of these cyclohexane-1,3-dione derivatives, have a more intensive action 
on grassy plants than herbicidal agents containing merely an 
N-azolylmethylacetanilide of the formula I or a cyclohexane-1,3-dione of 
the formula II. Surprisingly, N-azolylmethylacetanilides of the formula I 
and cyclohexane-1,3-diones of the formula II exhibit in these mixtures a 
pronounced synergistic action, especially at application rates at which 
one or both components have only insufficient action. 
Suitable mixture components of the formula I are 
N-azolylmethylhaloacetanilides in which R is hydrogen, alkyl of a maximum 
of 5 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 
sec-butyl, isobutyl, tert-butyl, or n-pentyl and branched pentyl, or 
alkoxy of a maximum of 5 carbon atoms, such as methoxy, ethoxy, propoxy, 
butoxy, or pentoxy; R.sup.1 and R.sup.2 are identical or different and 
each denotes hydrogen, halogen, such as fluorine, chlorine, bromine and 
iodine, alkyl of a maximum of 5 carbon atoms, such as methyl, ethyl, 
n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl 
and branched pentyl, or alkoxy of a maximum of 5 carbon atoms, such as 
methoxy, ethoxy, propoxy, butoxy, or pentoxy; R and R.sup.2 together 
denote an ortho-position alkylene chain of a maximum of 6 carbon atoms 
which is unsubstituted or substituted by alkyl of a maximum of 4 carbon 
atoms, such as ethylene, trimethylene, tetramethylene, 
1-methyltrimethylene, 1,1-dimethyltrimethylene, and 
1,1-dimethyltetramethylene; X denotes chlorine or bromine, preferably 
chlorine; and A denotes azole attached via a ring nitrogen atom, such as 
pyrrole, pyrazole, imidazole, 1,2,4 -triazole, 1,2,3-triazole and 
tetrazole, which is unsubstituted or mono- or polysubstituted 
independently by halogen, phenyl, alkyl, alkoxy, alkylthio or 
perfluoroalkyl, each of a maximum of 4 carbon atoms, cyano, carboxy, 
carbalkoxy of a maximum of 4 carbon atoms in the alkoxy, or alkanoyl of a 
maximum of 4 carbon atoms, such as 2,6-dimethylpyrrole, 
tetramethylpyrrole, 3(5)-methylpyrazole, 4-methylpyrazole, 
3(5)-ethylpyrazole, 4-ethylpyrazole, 3(5)-isopropylpyrazole, 
4-isopropylpyrazole, 3,5-dimethylpyrazole, 3,5-dimethyl-4-acetylpyrazole, 
3,5-dimethyl-4-propionylpyrazole, 3,4,5-trimethylpyrazole, 
3(5)-phenylpyrazole, 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, 3,5-dimethyl-4-chloropyrazole, 
3,5-dimethyl-4-bromopyrazole, 4-chloro-3(5)-methylpyrazole, 
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-methoxy-3,5-dichloropyrazole, 4,5-dichloroimidazole, 
2-methyl-4,5-dichloroimidazole, 2-ethyl-4,5-dichloroimidazole, 
3(5)-methyl-1,2,4-triazole, 3,5-dimethyl-1,2,4-triazole, 
3(5)-chloro-1,2,4-triazole, 3(5)-bromo-1,2,4-triazole, 
3(5)-chloro-5(3)-methyl-1,2,4-triazole, 3,5-dichloro-1,2,4-triazole, 
3,5-dibromo-1,2,4-triazole, 3(5)-chloro-5(3)-cyano-1,2,4-triazole, 
3(5)-chloro-5(3)-phenyl-1,2,4-triazole, 
3(5)-chloro-5(3)-carbomethoxy-1,2,4-triazole, 
3(5)-methylthio-1,2,4-triazole, 4(5)-methyl-1,2,3-triazole, 
4,5-dimethyl-1,2,3-triazole, 4(5)-phenyl-1,2,3-triazole, 
4(5)-chloro-1,2,3-triazole, 1,2,3-triazol-4(5)-yl-carboxylic acid ethyl 
ester, 1,2,3-triazol-4,5-yl-dicarboxylic acid dimethyl ester, 
5-methyltetrazole, 5-chlorotetrazole, and tetrazolyl-5-carboxylic acid 
ethyl ester. 
When the substituted or unsubstituted azole contains 2 or 3 nitrogen atoms, 
A may also be attached in a saltlike manner to one of the conventional 
strong inorganic or organic acids, such as hydrochloric acid, hydrobromic 
acid, nitric acid, sulfuric acid, tetrafluoboric acid, fluosulfonic 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, or an arylsulfonic acid, e.g., 
dodecylbenzenesulfonic acid. 
Preferred acetanilides are those which bear, in the 2- and 6-positions on 
the phenyl ring, methyl or ethyl and, in the 3-position, hydrogen, methyl 
or ethyl, suitable azoles being pyrazole, triazoles, or tetrazole, each of 
which may be substituted by lower alkyl, alkoxy, carbalkoxy, cyano or 
halogen. 
In particular, the herbicidal agents according to the invention contain the 
following N-azolylmethylhaloacetanilides: 
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-2',6'-dimethyl-N-(4-methylpyrazol-1-yl-methyl)-acetanilide, 
2-chloro-2'-methyl-6'-ethyl-N-(4-methoxypyrazol-1-yl-methyl)-acetanilide, 
2-chloro-2'-methyl-5'-ethyl-N-(3(5)-methylpyrazol-1-yl)-acetanilide, 
2-chloro-2',6'-dimethyl-N-(3,5-dimethylpyrazol-1-yl-methyl)-acetanilide, 
2-chloro-2',6'-dimethyl-N-(1,2,4-triazol-1-yl-methyl)-acetanilide, 
2-chloro-2',6'-dimethyl-N-(4-chloropyrazol-1-yl-methyl)-acetanilide, 
2-chloro-2',3',6'-trimethyl-N-(pyrazol-1-yl-methyl)-acetanilide, 
2-chloro-2'-methyl-6'-ethyl-N-(3,5-dimethyl-pyrazol-1-yl-methyl)-acetanili 
de, 
2-chloro-2',6'-diethyl-N-(3,5-dimethyl-pyrazol-1-yl-methyl)-acetanilide, 2 
-chloro-2',3',6'-trimethyl-N-(3,5-dimethyl-pyrazol-1-yl-methyl)-acetanilide 
, 2-chloro-2',6'-diethyl-N-(4-methylpyrazol-1-yl-methyl)-acetanilide, 
2-chloro-2'-methyl-6'-ethyl-N-(4-methylpyrazol-1-yl-methyl)-acetanilide, 
2-chloro-2',3',6'-trimethyl-N-(4-methylpyrazol-1-yl-methyl)-acetanilide, 
2-chloro-2',6'-dimethyl-N-(3-(5)-methylpyrazol-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-yl-methyl)-acetanilide, 
2-chloro-2',6'-diethyl-N-(pyrazol-1 -yl-methyl)-acetanilide, 
2-chloro-2'-methyl-6'-ethyl-N-(1,2,4-triazol-1-yl-methyl)-acetanilide, 
2-chloro-2',6'-diethyl-N-(1,2,4-triazol-1-yl-methyl)-acetanilide, 
2-chloro-2',3',6'-trimethyl-N-(1,2,4-triazol-1-yl-methyl)-acetanilide, 
2-bromo-2',6'-dimethyl-N-(pyrazol-1-yl-methyl)-acetanilide and 
2-bromo-2'-methyl-6'-ethyl-N-(pyrazol-1-yl-methyl)-acetanilide. 
Suitable mixture components of the formula II are for example 
cyclohexane-1,3-dione derivatives in which R.sup.1 is alkyl of a maximum 
of 4 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 
phenyl, or phenyl or benzyl substituted by halogen, alkyl or alkoxy of a 
maximum of 4 carbon atoms, such as 4-chlorophenyl, 2-methylphenyl, 
3-methylphenyl, 4-methylphenyl, 2,5-dimethylphenyl, 2,4-dichlorophenyl and 
4-methoxyphenyl; R.sup.2 denotes alkyl of a maximum of 4 carbon atoms, 
such as methyl, ethyl, n-propyl and n-butyl; R.sup.3 denotes alkyl or 
alkenyl of a maximum of 4 carbon atoms, such as ethyl and allyl; R.sup.4 
denotes hydrogen or alkoxycarbonyl of a maximum of 5 carbon atoms, such as 
methoxycarbonyl and ethoxycarbonyl; X denotes alkylene of a maximum of 4 
carbon atoms, such as methylene, ethylene, methylethylene or 
ethylmethylene; and n denotes one of the integers 0, 1 and 2. The 
compounds may also be in the form of metal or ammonium salts, e.g., alkali 
metal or alkaline earth metal salts, such as sodium, potassium, calcium or 
barium salts, as manganese, copper, zinc, cobalt, iron or silver salts, or 
as tetrabutylammonium, trimethylbutylammonium or 
dimethylbenzylhexadecylammonium salts. 
Preferred mixture components of the formula II are those in which R.sup.1 
is alkyl of 1 to 3 carbon atoms, phenyl, or phenyl substituted by 
chlorine, methyl or methoxy, R.sup.2 is alkyl of 2 or 3 carbon atoms, 
R.sup.3 is ethyl or allyl, R.sup.4 is hydrogen, and X is linear or 
branched alkylene of 1 to 3 carbon atoms. 
The ratio of the components to each other may vary widely; the ratio 
selected depends first and foremost on the spectrum of weeds and grasses 
to be combated, and possibly also on the development stage of the plants 
to be combated. The ratio of N-azolylmethylhaloacetanilide of the formula 
I to cyclohexane-1,3-dione derivative of the formula II is preferably from 
1:0.125 to 1:10 parts by weight. 
The amount of pure active ingredient mixture in the herbicidal agents 
according to the invention which is necessary for combating unwanted plant 
growth depends on the type of soil, the composition of the stand, and the 
climatic conditions prevailing where the agents are to be used. Generally, 
application rates are from 0.1 to 5 kg of active ingredient mixture per 
hectare. 
Crops in which the herbicidal agents according to the invention may be used 
are essentially those in which the individual components may be employed, 
e.g., rape and other cabbage varieties, groundnuts, cotton, potatoes 
(Irish potatoes), sugarbeets, soybeans, established alfalfa, strawberries 
and numerous other, annual or perennial, herbaceous or woody crop plants. 
The application method employed is of importance here. The agents according 
to the invention may be applied either pre- or postemergence in crop and 
unwanted plants. Further, a special application technique is also suitable 
in which the spray is directed in such a manner that the leaves of the 
crop plants come as little as possible into contact with the agents, and 
the unwanted plants growing among or below them, or the soil are contacted 
(post-directed, lay-by). 
In view of the many application methods possible, the agents according to 
the invention, or compositions containing them, may be used in a large 
number of crops for removing unwanted plant growth.

The following crop plants may be mentioned by way of example: 
______________________________________ 
Botanical name Common name 
______________________________________ 
Allium cepa onions 
Ananas comosus pineapples 
Arachis hypogaea peanuts (groundnuts) 
Asparagus officinalis 
asparagus 
Beta vulgaris spp. altissima 
sugarbeets 
Beta vulgaris spp. rapa 
fodder beets 
Beta vulgaris spp. esculenta 
table beets, red beets 
Brassica napus var. napus 
rape 
Brassica napusvar. napobrassica 
Brassica napus var. rapa 
turnips 
Brassica rapa var. silvestris 
Camellia sinensis tea plants 
Carthamus tinctorius 
safflower 
Carya illinoinensis 
pecan trees 
Citrus limon lemons 
Citrus maxima grapefruits 
Citrus reticulata 
Citrus sinensis orange trees 
Coffea arabica (Coffea canephora, 
Coffea liberica) coffee plants 
Cucumis melo melons 
Cucumis sativus cucumbers 
Cynodon dactylon Bermudagrass in turf 
and lawns 
Daucus carota carrots 
Elais guineensis oil palms 
Fragaria vesca strawberries 
Glycine max soybeans 
Gossypium hirsutum 
(Gossypium arboreum 
cotton 
Gossypium herbaceum 
Gossypium vitifolium) 
Helianthus annuus sunflowers 
Helianthus tuberosus 
Hevea brasiliensis 
rubber plants 
Humulus lupulus hops 
Ipomoea batatas sweet potatoes 
Juglans regia walnut trees 
Lactuca sativa lettuce 
Lens culinaris lentils 
Linum usitatissimum 
flax 
Lycopersicon lycopersicum 
tomatoes 
Malus spp. apple trees 
Manihot esculenta cassava 
Medicago sativa alfalfa (lucerne) 
Mentha piperita peppermint 
Musa spp. banana plants 
Nicothiana tabacum 
tobacco 
(N. rustica) 
Olea europaea olive trees 
Oryza sativa rice 
Panicum miliaceum 
Phasedus lunatus limabeans 
Phaseolus mungo mungbeans 
Phaseolus vulgaris 
snapbeans, green beans, 
Petroselinum crispum 
parsley 
spp. tuberosum 
Picea abies Norway spruce 
Abies alba fir trees 
Pinus spp. pine trees 
Pisum sativum English peas 
Prunus avium cherry trees 
Prunus domestica plum trees 
Prunus dulcis almond trees 
Prunus persica peach trees 
Pyrus communis pear trees 
Ribes sylvestre redcurrants 
Ribes uva-crispa 
Ricinus communis 
Saccharum officinarum 
sugar cane 
Sesamum indicum sesame 
Solanum tuberosum Irish potatoes 
Sorghum bicolor (s. vulgare) 
grain sorghum 
Sorghum dochna 
Spinacia oleracea spinach 
Theobroma cacao cacao plants 
Trifolium pratense 
red clover 
Vaccinium corymbosum 
blueberries 
Vaccinium vitis-idaea 
cranberries 
Vicia faba tick beans 
Vigna sinensis (V. unguiculata) 
cow peas 
Vitis vinifera grapes 
Zea mays Indian corn, sweet corn, maize 
______________________________________ 
The herbicidal agents according to the invention are applied for instance 
in the form of directly sprayable solutions, powders, suspensions 
(including high-percentage aqueous, oily or other suspensions), 
dispersions, emulsions, oil dispersions, pastes, dusts, broadcasting 
agents, or granules by spraying, atomizing, dusting, broadcasting or 
watering. The forms of application depend entirely on the purpose for 
which the agents are being used; in any case they should ensure as fine a 
distribution of the active ingredient as possible. 
For the preparation of solutions, emulsions, pastes and oil dispersions to 
be sprayed direct, mineral oil fractions of medium to high boiling point, 
such as kerosene or diesel oil, further coal-tar oils, and oils of 
vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons 
such as benzene, toluene, xylene, paraffin, tetrahydronaphthalene, 
alkylated naphthalenes and their derivatives such as methanol, ethanol, 
propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, 
cyclohexanone, chlorobenzene, isophorone, etc., and strongly polar 
solvents such as dimethylformamide, dimethylsulfoxide, 
N-methylpyrrolidone, water, etc. are suitable. 
Aqueous formulations may be prepared from emulsion concentrates, pastes, 
oil dispersions or wettable powders by adding water. To prepare emulsions, 
pastes and oil dispersions the ingredients as such or dissolved in an oil 
or solvent may be homogenized in water by means of wetting or dispersing 
agents, adherents or emulsifiers. Concentrates which are suitable for 
dilution with water may be prepared from active ingredient, wetting agent, 
adherent, emulsifying or dispersing agent and possibly solvent or oil. 
Examples of surfactants are: alkali metal, alkaline earth metal and 
ammonium salts of ligninsulfonic acid, naphthalenesulfonic acids, 
phenolsulfonic acids, alkylaryl sulfonates, alkyl sulfates, and alkyl 
sulfonates, alkali metal and alkaline earth metal salts of 
dibutylnaphthalenesulfonic acid, lauryl ether sulfate, fatty alcohol 
sulfates, alkali metal and alkaline earth metal salts of fatty acids, 
salts of sulfated hexadecanols, heptadecanols, and octadecanols, salts of 
sulfated fatty alcohol glycol ethers, condensation products of sulfonated 
naphthalene and naphthalene derivatives with formaldehyde, condensation 
products of naphthalene or naphthalenesulfonic acids with phenol and 
formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated 
isooctylphenol, ethoxylated octylphenol and ethoxylated nonylphenol, 
alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl 
polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide 
condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, 
ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, 
sorbitol esters, lignin, sulfite waste liquors and methyl cellulose. 
Powders, dusts and broadcasting agents may be prepared by mixing or 
grinding the active ingredients with a solid carrier. 
Granules, e.g., coated, impregnated or homogeneous granules, may be 
prepared by bonding the active ingredients to solid carriers. Examples of 
solid carriers are mineral earths such as silicic acid, silica gels, 
silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bole, loess, 
clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, 
magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, 
ammonium phosphate, ammonium nitrate, and ureas, and vegetable products 
such as grain flours, bark meal, wood meal, and nutshell meal, cellulosic 
powders, etc. 
The formulations contain from 0.1 to 95, and preferably 0.5 to 90, % by 
weight of active ingredient mixture. 
Examples of formulations are given below. 
I. 20 parts by weight of a mixture of 1 part by weight of 
2-chloro-2',6'-dimethyl-N-(pyrazol-1-yl-methyl)-acetanilide and 2 parts by 
weight of 
2-(1-ethoxyaminobutylidene)-5-(2-ethylthiopropyl)-cyclohexane-1,3-dione is 
dissolved in a mixture consisting of 80 parts by weight of xylene, 10 
parts by weight of the adduct of 8 to 10 moles of ethylene oxide with 1 
mole of oleic acid-N-monoethanolamide, 5 parts by weight of the calcium 
salt of dodecylbenzenesulfonic acid, and 5 parts by weight of the adduct 
of 40 moles of ethylene oxide with 1 mole of castor oil. By pouring the 
solution into 100,000 parts by weight of water and uniformly distributing 
it therein, an aqueous dispersion is obtained containing 0.02% by weight 
of the active ingredient mixture. 
II. 20 parts by weight of a mixture of 1 part by weight of 
2-chloro-2',6'-dimethyl-N-(pyrazol-1-yl-methyl)-acetanilide and 4 parts by 
weight of 
2-(1-ethoxyaminobutylidene)-5-(2-ethylthiopropyl)-cyclohexane-1,3-dione is 
dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 
30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 
moles of ethylene oxide with 1 mole of isooctylphenol, and 10 parts by 
weight of the adduct of 40 moles of ethylene oxide with 1 mole of castor 
oil. By pouring the solution into 100,000 parts by weight of water and 
finely distributing it therein, an aqueous dispersion is obtained 
containing 0.02% by weight of the active ingredient mixture. 
III. 3 parts by weight of a mixture of 1 part by weight of 
2-chloro-2',6'-dimethyl-N-(pyrazol-1-yl-methyl)-acetanilide and 1 part by 
weight of 
2-(1-ethoxyaminobutylidene)-5-(2-ethylthiopropyl)-cyclohexane-1,3-dione is 
intimately mixed with 97 parts by weight of particulate kaolin. A dust is 
obtained containing 3% by weight of the active ingredient mixture. 
IV. 20 parts by weight of a mixture of 4 parts by weight of 
2-chloro-2',6'-dimethyl-N-(pyrazol-1-yl-methyl)-acetanilide and 1 part by 
weight of 
2-(1-ethoxyaminobutylidene)-5-(2-ethylthiopropyl-cyclohexane-1,3-dione is 
intimately mixed with 2 parts of the calcium salt of 
dodecylbenzenesulfonic acid, 8 parts of a fatty alcohol polyglycol ether, 
2 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde 
condensate and 68 parts of a paraffinic mineral oil. A stable oily 
dispersion is obtained. 
V. 30 parts by weight of a mixture of 1 part by weight of 
2-chloro-2',6'-dimethyl-N-(pyrazol-1-yl-methyl)-acetanilide and 4 parts by 
weight of 
2-(1-ethoxyaminobutylidene)-5-(2-ethylthiopropyl)-cyclohexane-1,3-dione is 
intimately mixed with a mixture consisting of 92 parts by weight of 
powdered silica gel and 8 parts by weight of paraffin oil which has been 
sprayed onto the surface of this silica gel. A formulation of the active 
ingredient mixture is obtained having good adherence. 
The new herbicidal active ingredients according to the invention may be 
mixed and applied together with numerous representatives of other 
herbicidal or growth-regulating active ingredient groups. Examples of 
suitable mixture components are diazines, benzothiadiazinones, 
2,6-dinitroanilines, N-phenylcarbamates, thiolcarbamates, halocarboxylic 
acids, triazines, amides, ureas, diphenyl ethers, triazinones, uracils, 
benzofuran derivatives, etc. Such combinations broaden the spectrum of 
action. A number of active ingredients which, when combined with the new 
compounds, give mixtures useful for widely varying applications are given 
below by way of example: 
5-amino-4-chloro-2-phenyl-3(2H)-pyridazinone 
5-amino-4-bromo-2-phenyl-3(2H)-pyridazinone 
5-amino-4-chloro-2-cyclohexyl-3(2H)-pyridazinone 
5-amino-4-bromo-2-cyclohexyl-3(2H)-pyridazinone 
5-methylamino-4-chloro-2-(3-trifluoromethylphenyl)-3(2H)-pyridazinone 
5-methylamino-4-chloro-2-(3-.alpha.,.alpha.,.beta.,.beta.-tetrafluoroethoxy 
phenyl)-3-(2H)-pyridazinone 
5-dimethylamino-4-chloro-2-phenyl-3(2H)-pyridazinone 
4,5-dimethoxy-2-phenyl-3(2H)-pyridazinone 
4,5-dimethoxy-2-cyclohexyl-3(2H)-pyridazinone 
4,5-dimethoxy-2-(3-trifluoromethylphenyl)-3(2H)-pyridazinone 
5-methoxy-4-chloro-2-(3-trifluoromethylphenyl)-3(2H)-pyridazinone 
5-amino-4-bromo-2(3-methylphenyl)-3(2H)-pyridazinone 
3-(1-methylethyl)-1H-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide and salts 
3-(1-methylethyl)-8-chloro-1H-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide 
and salts 
3-(1-methylethyl)-8-fluoro-1H-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide 
and salts 
3-(1-methylethyl)-8-methyl-1H-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide 
and salts 
1-methoxymethyl-3-(1-methylethyl)-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxi 
de 
1-methoxymethyl-8-chloro-3-(1-methylethyl)-2,1,3-benzothiadiazin-4(3H)-one- 
2,2-dioxide 
1-methoxymethyl-8-fluoro-3-(1-methylethyl)-2,1,3-benzothiadiazin-4(3H)-one- 
2,2-dioxide 
1-cyano-8-chloro-3-(1-methylethyl)-2,1,3-benzothiadiazin-4(3H)-one-2,2-diox 
ide 
1-cyano-8-fluoro-3-(1-methylethyl)-2,1,3-benzothiadiazin-4(3H)-one-2,2-diox 
ide 
1-cyano-8-methyl-3-(1-methylethyl)-2,1,3-benzothiadiazin-4(3H)-one-2,2-diox 
ide 
1-cyano-3-(1-methylethyl)-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide 
1-azidomethyl-3-(1-methylethyl)-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide 
3-(1-methylethyl)-1H-pyridino-[3,2-e]-2,1,3-thiadiazin-(4)-one-2,2-dioxide 
N-(1-ethylpropyl)-2,6-dinitro-3,4-dimethylaniline 
N-(1-methylethyl)-N-ethyl-2,6-dinitro-4-trifluoromethylaniline 
N-n-propyl-N-.beta.-chloroethyl-2,6-dinitro-4-trifluoromethylaniline 
N-n-propyl-N-cyclopropylmethyl-2,6-dinitro-4-trifluoromethylaniline 
N-bis-(n-propyl)-2,8-dinitro-3-amino-4-trifluoromethylaniline 
N-bis-(n-propyl)-2,6-dinitro-4-methylaniline 
N-bis-(n-propyl)-2,6-dinitro-4-methylsulfonylaniline 
N-bis-(n-propyl)-2,6-dinitro-4-aminosulfonylaniline 
bis-(.beta.-chloroethyl)-2,6-dinitro-4-methylaniline 
N-ethyl-N-(2-methylallyl)-2,6-dinitro-4-trifluoromethylaniline 
3,4-dichlorobenzyl N-methylcarbamate 
2,6-di-tert.-butyl-4-methylphenyl N-methylcarbamate 
isopropyl N-phenylcarbamate 
3-methoxyprop-2-yl N-3-fluorophenylcarbamate 
isopropyl N-3-chlorophenylcarbamate 
but-1-yn-3-yl N-3-chlorophenylcarbamate 
4-chlorobut-2-yn-1-yl N-3-chlorophenylcarbamate 
methyl N-3,4-dichlorophenylcarbamate 
methyl N-(4-aminobenzenesulfonyl)-carbamate 
O-(N-phenylcarbamoyl)-propanone oxime 
N-ethyl-2-(phenylcarbamoyl)-oxypropionic acid amide 
3'-N-isopropylcarbamoyloxypropionanilide 
ethyl-N-(3-(N'-phenylcarbamoyloxy)-phenyl)-carbamate 
methyl-N-(3-(N'-methyl-N'-phenylcarbamoyloxy)-phenyl)-carbamate 
isopropyl-N-(3-(N'-ethyl-N'-phenylcarbamoyloxy)-phenyl)-carbamate 
methyl-N-(3-(N'-3-methylphenylcarbamoyloxy)-phenyl)-carbamate 
methyl-N-(3-(N'-4-fluorophenylcarbamoyloxy)-phenyl)-carbamate 
methyl-N-(3-(N'-3-chloro-4-fluorophenylcarbamoyloxy)-phenyl)-carbamate 
ethyl-N-[3-N'-(3-chloro-4-fluorophenylcarbamoxyloxy)-phenyl]-carbamate 
ethyl-N-[3-N'-(3,4-difluorophenylcarbamoyloxy)-phenyl]-carbamate 
methyl-N-[3-(N'-3,4-difluorophenylcarbamoyloxy)-phenyl]-carbamate 
methyl N-3-(4'-fluorophenoxycarbonylamino)-phenylcarbamate 
ethyl N-3-(2'-methylphenoxycarbonylamino)-phenylcarbamate 
methyl N-3-(4'-fluorophenoxycarbonylamino)-phenylthiolcarbamate 
methyl N-3-(2',4',5'-trimethylphenoxycarbonylamino)-phenylthiolcarbamate 
methyl N-3-(phenoxycarbonylamino)-phenylthiolcarbamate 
p-chlorobenzyl N,N-diethylthiocarbamate 
ethyl N,N-di-n-propylthiolcarbamate 
n-propyl N,N-di-n-propylthiolcarbamate 
2,3-dichloroallyl N,N-diisopropylthiolcarbamate 
2,3,3-trichloroallyl N,N-diisopropylthiolcarbamate 
3-methyl-5-isoxazolylmethyl N,N-diisopropylthiolcarbamate 
3-ethyl-5-isoxazolylmethyl N,N-diisopropylthiolcarbamate 
ethyl N,N-di-sec.-butylthiolcarbamate 
benzyl N,N-di-sec.-butylthiolcarbamate 
ethyl N-ethyl-N-cyclohexylthiolcarbamate 
ethyl N-ethyl-N-bicyclo-[2.1.1]-heptylthiolcarbamate 
S-(2,3,3-trichloroallyl)-(2,2,4-trimethylazetidine)-1-carbothiolate 
S-ethylhexahydro-1-H-azepine-1-carbothiolate 
S-benzyl-(3-methylhexahydro-1-H-azepine-1)-carbothiolate 
S-benzyl-(2,3-dimethylhexahydro-1-H-azepine-1)-carbothiolate 
S-ethyl-(3-methylhexahydro-1-H-azepine-1)-carbothiolate 
n-propyl N-ethyl-N-n-butylthiolcarbamate 
2-chloroallyl N,N-dimethyldithiocarbamate 
N-methyldithiocarbamic acid, sodium salt 
trichloroacetic acid, sodium salt 
.alpha.,.alpha.-dichloropropionic acid, sodium salt 
.alpha.,.alpha.-dichlorobutyric acid, sodium salt 
.alpha.,.alpha.-.beta.,.beta.-tetrafluoropropionic acid, sodium salt 
.alpha.-methyl-.alpha.,.beta.-dichloropropionic acid, sodium salt 
methyl .alpha.-chloro-.beta.-(4-chlorophenyl)-propionate 
methyl .alpha.,.beta.-dichloro-.beta.-phenylpropionate 
benzamido oxyacetic acid 
2,3,5-triiodobenzoic acid (salts, esters, amides) 
2,3,6-trichlorobenzoic acid (salts, esters, amides) 
2,3,5,6-tetrachlorobenzoic acid (salts, esters, amides) 
2-methoxy-3,6-dichlorobenzoic acid (salts, esters, amides) 
2-methoxy-3,5,6-trichlorobenzoic acid (salts, esters, amides) 
3-amino-2,5,6-trichlorobenzoic acid (salts, esters, amides) 
O,S-dimethyltetrachlorothioterephthalate 
dimethyl-2,3,5,6-tetrachloroterephthalate 
disodium-3,6-endoxohexahydrophthalate 
4-amino-3,5,6-trichloropicolinic acid (salts) 
ethyl 2-cyano-3-(N-methyl-N-phenyl)-aminoacrylate 
isobutyl 2-[4-(4'-chlorophenoxy)-phenoxy]-propionate 
methyl 2-[4-(2',4'-dichlorophenoxy)-phenoxy]-propionate 
methyl 2-[4-(4'-trifluoromethylphenoxy)-phenoxy]-propionate 
2-[4-(2'-chloro-4'-trifluorophenoxy)-phenoxy]-propionic acid, sodium salt 
2-[4-(3',5'-dichloropyridyl-2-oxy)-phenoxy]-propionic acid, sodium salt 
ethyl 2-(N-benzoyl-3,4-dichlorophenylamino)-propionate 
methyl 2-(N-benzoyl-3-chloro-4-fluorophenylamino)-propionate 
isopropyl 2-(N-benzoyl-3-chloro-4-fluorophenylamino)-propionate 
2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine 
2-chloro-4-ethylamino-6-(amino-2'-propionitrile)-1,3,5-triazine 
2-chloro-4-ethylamino-6-(2-methoxypropyl)-2-amino-1,3,5-triazine 
2-chloro-4-ethylamino-6-butyn-1-yl-2-amino-1,3,5-triazine 
2-chloro-4,6-bisethylamino-1,3,5-triazine 
2-chloro-4,6-bisisopropylamino-1,3,5-triazine 
2-chloro-4-isopropylamino-6-cyclopropylamino-1,3,5-triazine 
2-azido-4-methylamino-6-isopropylamino-1,3,5-triazine 
2-methylthio-4-ethylamino-6-isopropylamino-1,3,5-triazine 
2-methylthio-4-ethylamino-6-tert.butylamino-1,3,5-triazine 
2-methylthio-4,6-bisethylamino-1,3,5-triazine 
2-methylthio-4,6-bisisopropylamino-1,3,5-triazine 
2-methoxy-4-ethylamino-6-isopropylamino-1,3,5-triazine 
2-methoxy-4,6-bisethylamino-1,3,5-triazine 
2-methoxy-4,6-bisisopropylamino-1,3,5-triazine 
4-amino-6-tert.butyl-3-methylthio-4,5-dihydro-1,2,4-triazin-5-one 
4-amino-6-phenyl-3-methyl-4,5-dihydro-1,2,4-triazin-5-one 
4-isobutylidenamino-6-tert.butyl-3-methylthio-4,5-dihydro-1,2,4-triazin-5-o 
ne 
1-methyl-3-cyclohexyl-6-dimethylamino-1,3,5-triazin-2,4-dione 
3-tert.butyl-5-chloro-6-methyluracil 
3-tert.butyl-5-bromo-6-methyluracil 
3-isopropyl-5-bromo-6-methyluracil 
3-sec.butyl-5-bromo-6-methyluracil 
3-(2-tetrahydropyranyl)-5-chloro-6-methyluracil 
3-(2-tetrahydropyranyl)-5,6-trimethyleneuracil 
3-cyclohexyl-5,6-trimethyleneuracil 
2-methyl-4-(3'-trifluoromethylphenyl)-tetrahydro-1,2,4-oxadiazine-3,5-dione 
2-methyl-4-(4'-fluorophenyl)-tetrahydro-1,2,4-oxadiazine-3,5-dione 
3-amino-1,2,4-triazole 
1-allyloxy-1-(4-bromophenyl)-2-[1',2',4'-triazolyl-(1')]-ethane (salts) 
1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,3-triazol-1-yl)-butan-2-one 
N,N-diallylchloroacetamide 
N-isopropyl-2-chloroacetanilide 
N-(but-1-yn-3-yl)-2-chloroacetanilide 
2-methyl-6-ethyl-N-propargyl-2-chloroacetanilide 
2-methyl-6-ethyl-N-ethoxymethyl-2-chloroacetanilide 
2-methyl-6-ethyl-N-(2-methoxy-1-methylethyl)-2-chloroacetanilide 
2-methyl-6-ethyl-N-(isopropoxycarbonylethyl)-2-chloroacetanilide 
2-methyl-6-ethyl-N-(4-methoxypyrazol-1-yl-methyl)-2-chloro-acetanilide 
2-methyl-6-ethyl-N-(pyrazol-1-yl-methyl)-2-chloroacetanilide 
2,6-dimethyl-N-(pyrazon-1-yl-methyl)-2-chloroacetanilide 
2,6-dimethyl-N-(4-methylpyrazol-1-yl-methyl)-2-chloro-acetanilide 
2,6-dimethyl-N-(1,2,4-triazol-1-yl-methyl)-2-chloroacetanilide 
2,6-dimethyl-N-(3,5-dimethylpyrazol-1-yl-methyl)-2-chloroacetanilide 
2,6-dimethyl-N-(1,3-dioxolan-2-yl-methyl)-2-chloroacetanilide 
2,6-dimethyl-N-(2-methoxyethyl)-2-chloroacetanilide 
2,6-dimethyl-N-isobutoxymethyl-2-chloroacetanilide 
2,6-diethyl-N-methoxymethyl-2-chloroacetanilide 
2,6-diethyl-N-n-butoxymethyl-2-chloroacetanilide 
2,6-diethyl-N-ethoxycarbonylmethyl-2-chloroacetanilide 
2,3,6-trimethyl-N-(pyrazol-1-yl-methyl)-2-chloroacetanilide 
2,3-dimethyl-N-isopropyl-2-chloroacetanilide 
2-(2-methyl-4-chlorophenoxy-N-methoxyacetamide 
2-(.alpha.-naphthoxy)-N,N-diethylpropionamide 
2,2-diphenyl-N,N-dimethylacetamide 
.alpha.-(3,4,5-tribromopyrazol-1-yl)-N,N-dimethylpropionamide 
N-(1,1-dimethylpropynyl)-3,5-dichlorobenzamide 
N-1-naphthylphthalamic acid 
propionic acid 3,4-dichloroanilide 
cyclopropanecarboxylic acid 3,4-dichloroanilide 
methacrylic acid 3,4-dichloroanilide 
2-methylpentanecarboxylic acid 3,4-dichloroanilide 
N-2,4-dimethyl-5-(trifluoromethyl)-sulfonylaminophenylacetamide 
N-4-methyl-5-(trifluoromethyl)-sulfonylaminophenylacetamide 
2-propionylamino-4-methyl-5-chlorothiazole 
O-(methylsulfonyl)-glycolic acid N-ethoxymethyl-2,6-dimethylanilide 
O-(methylaminosulfonyl)-glycolic acid N-isopropylanilide 
O-(isopropylaminosulfonyl)-glycolic acid N-but-1-yn-3-yl-anilide 
O-(methylaminosulfonyl)-glycolic acid hexamethyleneamide 
2,6-dichlorothiobenzamide 
2,6-dichlorobenzonitrile 
3,5-dibromo-4-hydroxybenzonitrile (salts) 
3,5-diiodo-4-hydroxybenzonitrile (salts) 
3,5-dibromo-4-hydroxy-O-2,4-dinitrophenylbenzaldoxime (salts) 
3,5-dibromo-4-hydroxy-O-2-cyano-4-nitrophenylbenzaldoxime (salts) 
pentachlorophenol, sodium salt 
2,4-dichlorophenyl-4'-nitrophenyl ether 
2,4,6-trichlorophenyl-4'-nitrophenyl ether 
2-fluoro-4,6-dichlorophenyl-4'-nitrophenyl ether 
2-chloro-4-trifluoromethylphenyl-4'-nitrophenyl ether 
2,4'-dinitro-4-trifluoromethyl-diphenyl ether 
2,4-dichlorophenyl-3'-methoxy-4'-nitro-phenyl ether 
2-chloro-4-trifluoromethylphenyl-3'-ethoxy-4'-nitro-phenyl ether 
2-chloro-4-trifluoromethylphenyl-3'-carboxy-4'-nitro-phenyl ether (salts) 
2,4-dichlorophenyl-3'-methoxycarbonyl-4'-nitro-phenyl ether 
2-(3,4-dichlorophenyl)-4-methyl-1,2,4-oxadiazolidine-3,5-dione 
2-(3-tert.butylcarbamoyloxyphenyl)-4-methyl-1,2,4-oxadiazolidine-3,5-dione 
2-(3-isopropylcarbamoyloxyphenyl)-4-methyl-1,2,4-oxadiazolidine-3,5-dione 
2-phenyl-3,1-benzoxazinone-(4) 
(4-bromophenyl)-3,4,5,9,10-pentaazatetracyclo-[5,4,1,0.sup.2,6, 0,.sup.8,11 
]-dodeca-3,9-diene 
2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranylmethane sulfonate 
2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranyldimethylaminosulfate 
2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranyl-(N-methyl-N-acetyl)-aminos 
ulfonate 
3,4-dichloro-1,2-benzisothiazole 
N-4-chlorophenyl-allylsuccinimide 
2-methyl-4,6-dinitrophenol (salts, esters) 
2-sec.butyl-4,6-dinitrophenol (salts, esters) 
2-sec.butyl-4,6-dinitrophenol acetate 
2-tert.butyl-4,6-dinitrophenol acetate 
2-tert.butyl-4,6-dinitrophenol (salts) 
2-tert.butyl-5-methyl-4,6-dinitrophenol (salts) 
2-tert.butyl-5-methyl-4,6-dinitrophenol acetate 
2-sec.amyl-4,6-dinitrophenol (salts, esters) 
1-(.alpha.,.alpha.-dimethylbenzyl)-3-(4-methylphenyl)-urea 
1-phenyl-3-(2-methylcyclohexyl)-urea 
1-phenyl-1-benzoyl-3,3-dimethylurea 
1-(4-chlorophenyl)-1-benzoyl-3,3-dimethylurea 
1-(4-chlorophenyl)-3,3-dimethylurea 
1-(4-chlorophenyl)-3-methyl-3-but-1-yn-3-yl-urea 
1-(3,4-dichlorophenyl)-3,3-dimethylurea 
1-(3,4-dichlorophenyl)-1-benzoyl-3,3-dimethylurea 
1-(3,4-dichlorophenyl)-3-methyl-3-n.butylurea 
1-(4-isopropylphenyl)-3,3-dimethylurea 
1-(3-trifluoromethylphenyl)-3,3-dimethylurea 
1-(.alpha.,.alpha.,.beta.,.beta.-tetrafluoroethoxyphenyl)-3,3-dimethylurea 
1-(3-tert.butylcarbamoyloxyphenyl)-3,3-dimethylurea 
1-(3-chloro-4-methylphenyl)-3,3-dimethylurea 
1-(3-chloro-4-methoxyphenyl)-3,3-dimethylurea 
1-(3,5-dichloro-4-methoxyphenyl)-3,3-dimethylurea 
1-[4-(4'-chlorophenoxy)-phenyl]-3,3-dimethylurea 
1-[4-(4'-methoxyphenoxy)-phenyl]-3,3-dimethylurea 
1-cyclooctyl-3,3-dimethylurea 
1-(hexahydro-4,7-methanoindan-5-yl)-3,3-dimethylurea 
1-[1- or 2-(3a,4,5,7,7a-hexahydro)-4,7-methanoindanyl]-3,3-dimethylurea 
1-(4-fluorophenyl)-3-carboxymethoxy-3-methylurea 
1-phenyl-3-methyl-3-methoxyurea 
1-(4-chlorophenyl)-3-methyl-3-methoxyurea 
1-(4-bromophenyl)-3-methyl-3-methoxyurea 
1-(3,4-dichlorophenyl)-3-methyl-3-methoxyurea 
1-(3-chloro-4-bromophenyl)-3-methyl-3-methoxyurea 
1-(3-chloro-4-isopropylphenyl)-3-methyl-3-methoxyurea 
1-(3-chloro-4-methoxyphenyl)-3-methyl-3-methoxyurea 
1-(3-tert.butylphenyl)-3-methyl-3-methoxyurea 
1-(2-benzthiazolyl)-1,3-dimethylurea 
1-(2-benzthiazolyl)-3-methylurea 
1-(5-trifluoromethyl-1,3,4-thiadiazolyl)-1,3-dimethylurea 
imidazolidin-2-one-1-carboxylic acid isobutylamide 
1,2-dimethyl-3,5-diphenylpyrazolium-methylsulfate 
1,2,4-trimethyl-3,5-diphenylpyrazolium-methylsulfate 
1,2-dimethyl-4-bromo-3,5-diphenylpyrazolium-methylsulfate 
1,3-dimethyl-4-(3,4-dichlorobenzoyl)-5-(4-methylphenylsulfonyloxy)-pyrazole 
2,3,5-trichloropyridinol-(4) 
1-methyl-3-phenyl-5-(3'-trifluoromethylphenyl)-pyridone-(4) 
1-methyl-4-phenylpyridinium chloride 
1,1-dimethylpyridinium chloride 
3-phenyl-4-hydroxy-6-chloropyridazine 
1,1'-dimethyl-4,4'-dipyridylium-di(methylsulfate) 
1,1'-di-(3,5-dimethylmorpholine-carbonylmethyl)-4,4'-dipyridylium 
dichloride 
1,1'-ethylene-2,2'-dipyridylium dibromide 
3-[1-(N-ethoxyamino)-propylidene]-6-ethyl-3,4-dihydro-2H-pyran-2,4-dione 
3-[1-(N-allyloxyamino)-propylidene]-6-ethyl-3,4-dihydro-2H-pyran-2,4-dione 
2-[1-(N-allyloxyamino)-propylidene]-5,5-dimethylcyclohexane-1,3-dione 
(salts) 
2-[1-(-allyloxyamino-butylidene]-5,5-dimethylcyclohexane-1,3-dione (salts) 
2-[1-(N-allyloxyamino-butylidene]-5,5-dimethyl-4-methoxycarbonyl-cyclohexan 
e-1,3-dione (salts) 
2-chlorophenoxyacetic acid (salts, esters, amides) 
4-chlorophenoxyacetic acid (salts, esters, amides) 
2,4-dichlorophenoxyacetic acid (salts, esters, amides) 
2,4,5-trichlorophenoxyacetic acid (salts, esters, amides) 
2-methyl-4-chlorophenoxyacetic acid (salts, esters, amides) 
3,5,6-trichloro-2-pyridinyl-oxyacetic acid (salts, esters, amides) 
methyl .alpha.-naphthoxyacetate 
2-(2-methylphenoxy)-propionic acid (salts, esters, amides) 
2-(4-chlorophenoxy)-propionic acid (salts, esters, amides) 
2-(2,4-dichlorophenoxy)-propionic acid (salts, esters, amides) 
2-(2,4,5-trichlorophenoxy)-propionic acid (salts, esters, amides) 
2-(2-methyl-4-chlorophenoxy)-propionic acid (salts, esters, amides) 
4-(2,4-dichlorophenoxy)-butyric acid (salts, esters, amides) 
4-(2-methyl-4-chlorophenoxy)-butyric acid (salts, esters, amides) 
cyclohexyl-3-(2,4-dichlorophenoxy)-acrylate 
9-hydroxyfluorenecarboxylic acid-(9) (salts, esters) 
2,3,6-trichlorophenylacetic acid (salts, esters) 
4-chloro-2-oxobenzothiazolin-3-yl-acetic acid (salts, esters) 
gibelleric acid (salts) 
disodium methylarsonate 
monosodium salt of methylarsonic acid 
N-phosphonomethyl-glycine (salts) 
N,N-bis-(phosphonomethyl)-glycine (salts) 
2-chloroethyl 2-chloroethanephosphonate 
ammonium-ethyl-carbamoyl-phosphonate 
di-n-butyl-1-n-butylamino-cyclohexyl-phosphonate 
trithiobutylphosphite 
O,O-diisopropyl-5-(2-benzosulfonylaminoethyl)-phosphorodithionate 
2,3-dihydro-5,6-dimethyl-1,4-dithiin-1,1,4,4-tetraoxide 
5-tert.butyl-3-(2,4-dichloro-5-isopropoxyphenyl)-1,3,4-oxadiazolone-(2) 
4,5-dichloro-2-trifluoromethylbenzimidazole (salts) 
1,2,3,6-tetrahydropyridazine-3,6-dione (salts) 
succinic acid mono-N-dimethylhydrazide (salts) 
(2-chloroethyl)-trimethylammonium chloride 
(2-methyl-4-phenylsulfonyl)-trifluoromethanesulfone anilide 
1,1-dimethyl-4,6-diisopropyl-5-indanyl ethyl ketone 
sodium chlorate 
ammonium thiocyanate 
calcium cyanamide. 
It may also be useful to apply the mixtures according to the invention in 
admixture with other crop protection agents, e.g., agents for combating 
pests or phytopathogenic fungi or bacteria. The compounds may also be 
mixed with solutions of mineral matters used to remedy nutritional or 
trace element deficiencies. To initiate the herbicidal action, wetting 
agents, spreader-stickers and non-phytotoxic oils and oil concentrates may 
be added. 
The following greenhouse experiments and experiments in the open illustrate 
the synergistic increase in action achieved by the combined use of 
N-azolylmethylacetanilides of the formula I and cyclohexane-1,3-dione 
derivatives of the formula II in the herbicidal agents according to the 
invention. 
The vessels employed were plastic flowerpots having a volume of 300 
cm.sup.3, and which were filled with a sandy loam containing about 1.5% 
humus. The seeds of the test plants (cf. Table 1) were sown shallow, and 
separately, according to species. For the preemergence treatment, the 
active ingredients were applied to the surface of the soil immediately 
after the seeds had been sown. The individual active ingredients and 
mixtures thereof were emulsified or suspended in water as vehicle, and 
sprayed through finely distributing nozzles. After the agents had been 
applied, the vessels were lightly sprinkler-irrigated to induce 
germination and growth and to activate the chemical agents. Transparent 
plastic covers were than placed on the vessels until the plants had taken 
root. The cover ensured uniform germination of the plants, insofar as this 
was not impaired by the chemicals, and prevented readily volatile active 
ingredients from evaporating. The pots were set up in the 
greenhouse--species from warmer areas at from 25.degree. to 40.degree. C., 
and species from moderate climates at 15.degree. to 30.degree. C. The 
experiments were run for from 4 to 6 weeks. During this period, the plants 
were tended and their reactions to the various treatments assessed. 
In the experiments in the open, the agents were emulsified or suspended in 
water as vehicle, and applied, with the aid of a motor-driven plot spray 
mounted on a tractor, to small plots of loamy sand and loam of pH 5 to 6 
and containing from 1 to 1.5% humus. The crop plant selected was 
sugarbeet. To combat broadleaved weeds, a treatment was initially carried 
out, after sowing and before emergence of the crop and unwanted plants, 
with from 2.0 to 2.5 kg of the herbicide 
1-phenyl-4-amino-5-chloropyridazone-(6) per hectare instead of mechanical 
weeding. Eight weeks later, a second spraying was effected postemergence 
with the agents according to the invention, which is predominantly to 
control unwanted grasses. The development stages of the unwanted grasses 
ranged from still ungerminated seed in the soil to tillered plants 
unaffected by chloridazon. Where no rain fell, the plots were initially 
sprinkled to ensure normal growth of crop and unwanted plants. The 
experiments were run for several months. 
The following tables containing the compounds investigated, the application 
rates in kg/ha of active ingredient, and the plants used for the tests. 
The scale used for assessment was 0 to 100, 0 denoting no damage or normal 
emergence, and 100 denoting nonemergence or complete destruction of at 
least the visible plant parts. 
The following active ingredients were used: 
2-chloro-2',6'-dimethyl-N-(pyrazol-1-yl-methyl)-acetanilide (active 
ingredient A) 
2-(1-ethoxyaminobutylidene)-5-(2-ethylthiopropyl)-cyclohexane-1,3-dione and 
its Na salt (active ingredient B) 
To check the synergistic action arithmetically, the action of the 
individual compounds at varying application rates was first ascertained 
(dosage-action series). From these figures, the action theoretically to be 
expected when two components with a known action are mixed was then 
calculated by the method suggested by F. H. A. Rummens in Weed Science, 
23, 4 et seq., 1975. These calculated figures were then compared with the 
results actually obtained in the experiments for the mixtures. If the 
degree of damage recorded is greater than that calculated, the action is 
synergistic. 
Results 
The figures in Table 2 show that the degree of damage actually found in the 
grassy plants given by way of example exceeds that theoretically to be 
expected. These active ingredient combinations therefore have a 
synergistic action which goes beyond a purely additive action of the 
individual components. 
TABLE 1 
______________________________________ 
List of plant names 
Botanical name 
Abbreviation in tables 
Common name 
______________________________________ 
Alopecurus myosuroides 
Alopec. myosur. 
slender foxtail 
Beta vulgaris -- sugarbeets 
Brachiaria platyphylla 
Brachiaria plat. 
broadleaf 
signalgrass 
Echinochloa crus-galli 
Echinochl. c.g. 
barnyardgrass 
Hordeum vulgare 
Hord. vulgare barley 
Rottboellia exaltata 
Rottboellia ex. 
itchgrass 
______________________________________ 
TABLE 2 
__________________________________________________________________________ 
Synergistic herbicidal action of mixtures of A and B; preemergence 
treatment in the 
greenhouse 
Test plants and theoretical and actual damage 
Alopec. myosur. 
Brachiaria plat. 
Rottboellia ex. 
Hord. vulgare 
Active 
Appln. rate 
damage [%] 
damage [%] 
damage [%] 
damage [%] 
ingredient 
[kg/ha] 
calc..sup.+ 
found.sup.++ 
calc..sup.+ 
found.sup.++ 
calc..sup.+ 
found.sup.++ 
calc..sup.+ 
found.sup.++ 
__________________________________________________________________________ 
A + B 0.06 + 0.06 
83 98 76 92 24 58 72 95 
0.125 + 0.125 
89 100 89 98 33 68 95 99 
0.25 + 0.25 
93 100 95 98 41 72 99 99 
0.125 + 0.03 
86 98 75 82 20 45 89 97 
0.06 + 0.25 
92 98 87 95 28 50 97 97 
__________________________________________________________________________ 
.sup.+ theoretically calculated 
.sup.++ found 
TABLE 3 
______________________________________ 
Control of unwanted grasses in sugarbeets by synergistic 
action of mixtures of A and B; postemergence 
treatment in the open 
Test plants and damage [%] 
Active Appln. rate 
Beta 
ingredient 
[kg/ha] vulgaris Alopec. myosur. 
Echinochl. 
______________________________________ 
A 0.5 0 22 45 
1.0 0 48 52 
2.0 2 66 72 
B 0.5 0 71 87 
1.0 3 84 82 
A + B 1.0 + 0.25 
0 89 95 
1.0 + 0.5 0 95 100 
______________________________________ 
0 = no damage 
100 = plants destroyed