CS198173B2 - Herbicide - Google Patents

Abstract

1507545 4 - Alkoxy - 3,5 - dihalo anilides BASF AG 1 Aug 1975 [2 Aug 1974] 32220/75 Heading C2C The invention comprises compounds of Formula I wherein R<SP>1</SP> is methyl or ethyl; R<SP>2</SP> is C 2-5 alkyl, halo-C 1-4 alkyl or cyclopropyl and radicals X are independently chlorine or bromine which may be prepared by reacting an amine of Formula II with carboxylic acid derivative of Formula III where R<SP>3</SP> is -OH, halogen or 3 - Bromo - 4 - methoxynitrobenzene is prepared by reacting 4-nitroanisole with bromine in the presence of AlCl 3 , is then chlorinated in the presence of SbCl 5 to obtain 3-bromo-5-chloro-4- methoxynitrobenzene which is in turn reduced with Fe/HCl to 3-bromo-5-chloro-4-methoxy aniline. Herbicidal compositions comprise at least one compound of Formula I together with a liquid or solid carrier and optionally other active and inactive additives known in the art for use in herbicidal compositions.

Description

The invention relates to valuable novel substituted 3,5-dihalogenanilides, herbicidal compositions containing these compounds, a method of controlling unwanted plants with the help of these compounds and a process for the production of said compounds.

It is already known to use propionic acid 3,4-dichloroanilide or propionic acid 3-chloro-4-methoxyanilide as herbicides (see German Patent Specification No. 1039 779, British Patent Specification No. 903 766, DAS No. 1219 471, and U.S. Patent Publication No.

382,280].

Furthermore, it is known that, in the case of the known active substance 3,4-dichloroanilide propionic acid, both the change of substituents and their positions on the phenyl core and the change of the acid residue lead to a decrease in activity (R. Wegler, Chemie der Pflanzenschutz- und Schadlingsbekampfungsmittel) , Springer-Verlag 1970, Vol 2, pp 312). As a substitution pattern in the phenyl moiety, optimal in terms of activity, 3,4-disubstitution with chlorine is reported, and it was believed that this scheme could not be disrupted by the synthesis of otherwise substituted anilides.

It has now been found that the anilides of formula I,

Y

R _R O - ^^ - NH-C ° _from -R

X (i) in which

R1 is methyl or ethyl,

R 2 represents a halomethyl, ethyl, halenethyl, propyl, halopropyl, butyl, halobutyl, pentyl or cyclopropyl group, the radicals containing 3 to 5 carbon atoms being straight or branched, and

X is chlorine or bromine, they show a better herbicidal effect than the known active ingredient, especially in cereal and cotton crops.

In contrast to the prior art, i.e., in comparison with 3,4-dichloroanilide propionic acid, the active compounds according to the invention show a better herbicidal selectivity in cereal, rice, maize and cotton crops. Thus, for example, weeds of the species Echinochloa (hedgehog), Alopecurus (feathertail), Lolium (ryegrass), Echinochloa (Echinochloa), Echinochloa (Echinochloa), Echinochloa (Echinochloa), Echinochloa (Echinochloa) are extinct. Sinapis (mustard), Stellaria (chickweed) and Galium (bedstraw), while crops such as wheat,. corn, rice and cotton are less damaged than when the known active ingredient is applied.

The active compounds according to the invention can be obtained in a conventional manner by the reaction known per se

3,5-dichloro-4-methoxyaniline [C. de Traz, Helv. Chim. Acta 30, 323 (1947)], 3,5-dichloro-4-ethoxyoniline [G. · Ba ^ emni, Gazz. Chim. Italian. 59, 16 (1929)] or 3,5-dibromo-4-methoxyaniline [C. L. focksox by A.H. Fiske, Ber. 35, 1130 (1902)] with carboxylic acids, their anhydrides or chlorides. . The reaction is carried out, for example, by treating an oxime derivative of the general formula

in which

R1 and X are as defined above, reacting with an acid derivative of the formula

R 3 -CO-R 2 in which

R2 is as defined above o

R 3 represents a hydroxyl group, a halogen atom or the radical -O-CO-R 2.

Examples of active substances used in the context of the invention are:

Propionic acid 3,5-dichloro-4-methoxyamido,

3,5-Dichloro-1-ethotyl-propionic acid,

3,5-dibromo-4-methoxyanedione propionic acid,

3,5-dicClol-1-methoxyanilide

2-methvallar,

3,5-cyclopropanecarbonyl-4-chloro-4-methoxyanilide;

Isobutyric acid 3,5-dichloro-4-methoxyoxide,

3,5-Dichloro-4-ethoxy-oxilide acid

3,5-dibromo-4-methoxyanilide acid

2-methvlv1crové,

3,5-Dichloro-4-ethoxyonyl chloride

3,5-dibromo-4-methoxyanilide of cycloproponocarboxylic acid,

Isobutyric acid 3,5-dicmloro-4-ethoxyoxilide

Isobutyric acid 3,5-dibromo-4-methoxyanilide,

Chloroacetic acid 3,5-dichloro-4-methoxyanilide

3,5-bromoacetic acid dicloro-4-methoxyonilide,

3,5-Dichloro-4-methoxyanilide · dicloroacetic acid

Dicloroacetic acid 3,5-dibromo-4-methoxymoxilide,

3,5-dichloro-4-methoxy-oxilide acid

2-Chloropropylamine,

3,5-Dichloro-4-methoxyoxyl acid

3-chlorprcpicnova,

3,5-dichloro-4-methoxyoxilide of butyric acid,

3,5-dichloro-4-methoxyanilide acid

4-chloromethyl,

Pivalic acid 3,5-dichloro-4-methoxyanodide.

Resources. . according to the invention exhibit a strong herbicidal effect and can therefore be used as. means for controlling weeds, optionally as means for controlling undesirable plant growth. .

Reality, . whether these resources. acts as . total, or as selective means, depends largely on the amount of active agent that is administered per unit. areas.

Weeds or undesirable plants are understood to be all monocotyledonous dicotyledonous plants,. that grow where they are undesirable.

The flux may be effected by means of the invention. combat, for example, the following species:

grasses (Gramineae), such as crocodile spider (Cynodon spp.), woodworm (Digitoria spp.J, hedgehog (Ecmincchloo spp.), rind (Setoria spp.), millet (Panicum spp.), fox-tail (Lolium spp.), Sorghum (Sorglium spp.), Wheatgrass (Agropyron spp.), Grassgrass (Pholoris spp.), Bream (Apero spp.), Whitefly (Dactylis spp.), Oats (Avena spp.), Brome ( Bromus spp., Uniola spp., Poaspp., Leptochloa spp., Brachiaria spp., Eleusine (Eleusine spp.), Cenchrus spp., Sweetheart (Eragrostis spp.), Reed (Phragmites communis) and others, Cyperaceae, such as Carex spp., Cyperus spp., Scirpus spp., Eleocharis spp.

and other, dicotyledonous weeds such as Malvaceae, e.g., abutilon (Abutilon theorpasti), Sida spp., mallow (Malva spp.), Mumbai hemp (Hibiscus spp.), and others, asteraceae (Compositae), such as ragweed (Ambrosia). spp.), lettuce (Lactuca spp.), sparrow (Senecio spp.), sow (Sonchus spp.), beet (Xanthium spp.), cornflower (Centaurea spp.), coltsfoot (Tussllago spp.), collar (Lapsana) communis), marshmallow (Tagetes spp.), 'turan (Erigeron spp.),

Iva spp., Galinsoga spp., Taraxacum spp., Chrysanthemum spp., Bldens spp., Thistle (Cirsium spp.), Anthemis spp., Camomile (Matricaria spp. ), Wormwood (Artemisia spp.), Éclipa alba and others, Convolvulaceae, such as Convolvulus spp., Ipomoea spp., Jaquemontia tamnifolia, Cuscuta spp. and others, Crucifera such as Barbarea vulgaris, Brassica spp., Caipsella spp., Sisymbrium spp., Thlaspi spp., Mustard (Sinapis arvensis), Radish (Raphanus spp.), Arabidopsis thaliana Descurainia spp. osivka (Draba spp.), Coronopus Twin, cress (Lepidium spp.) and others, Geraniaceae weeds (geraniums) _with such pumpava (Erodium spp.J, geranium (Geranium spp.) and others, Portulacaceae (Portulacaceae) such as purslane (Portulaca spp.) And others, Primulaceae such as pimpernel (Anagallis arvensis), willow (L ysimachiaspp.) and others, Rubiaceae such as Richardia spp., Bedstraw (Galium spp.), Diodia spp.

and others, Scrophulariaceae, such as Linnaeus (Linaria spp.), Speedwell (Veronica spp.), Foxglove (Digiitalis spp.), and others, Solanaceae, such as Roach (Physalis spp.), Eggplant (Solanum). spp.), durman (Datura spp.), eggplant (Nicandra spp.) and others, Urticaceae such as nettle (Urtica spp.), violet (Violaceae) such as violet (Viola spp.) and others,

Zygophyllaceae such as tribulus terrestis and others,

Euphorbiaceae, such as the annual pheasant (Mercurialis annua) and the spurge (Euphorbia spp.), Carrot (Umbelliferae), such as carrot (Daucus carota), goat tetanus (Aethusa cynapium), Ammi majus and others,

Commelinaeae such as Commelina spp. and others, Labiatae, such as Lamium spp., Galeopsis spp. and others, Leguminosae, such as Medicago spp., Trifolium spp., Vicia spp.), Sesbania exaltata, pea (Lathyrus spp.), Cassla spp., Aeschynomene spec.

others, Plantain (Plantaginaceae) such as plantain (Plantago spp.) and others, Polygonaceae, such as cottonwood (Polygonum spp.), sorrel (Rumex spp.), buckwheat (Fagopyrum spp.) and others,

Aizoaceae such as Mollugo verticlllata and others, Amaranthaceae, such as Amaranthus spp., Alternanthera spp. and more,

Boraginaceae such as Amsinckia spp., Myostis spp., Stoneseed (Lithospermus spp.), Pilate (Anchusa spp.) And others, Caryophyllaceae, such as Chickweed (Stellarla), Spruce (Spergula spp.), Soap (Saponaria) spp.), Scleranthus annuus, Silene spp., Cerastium spp., Agrostemma githago and others, Chenopodiaceae such as Chenopodium spp. (Kochia spp.), Potassium salmon (Salsola sludge), oranges (Atriplex spp.), Monolepsis nuttalliana and others, Lythraceae such as Cuphea spp.

and others, Oxalldaceae, such as Oxalis spp., Ranunculaceae such as Ranunculus spp., Delphinium spp., Adonis spp. and others, Papaveraceae. ), such as Poppy (Papaver spp.), Common Fumitory (Fumaria officlnalis) and others, Evening primrose (Onagraceae), such as Jussiaea spp., Ludwigla spec, and others, and Rosaceae, such as Alchemillia spp. ), cinquefoil (Potentilla spp.) and others,

Potamogetonaceae such as Potamogeton spp. and others, such as Najadaceae, such as Najas spp.

and others, Marsileaceae such as Marsilea quadrifolia and others Polypodiaceae such as Pteridium aquilinum and others Alismataceae such as Alisma spp. Sagittaria sagittifolia) and others,

Butomaceae like

Buntomus umbellatus, Equisetaceae such as Horsetail (Equisetum spec.)

Pontderiaceae such as Monochoria vaginalis, Eichhornla spec, and Heteranthera spec., Cattail (Typhaceae) such as cattail (Typha spec.).

Application of the compounds of the invention takes the form of, for example, directly sprayable solutions, powders, suspensions, including high percentage aqueous, oily or other suspensions, dispersions, emulsions, oil dispersions, pastes, dusts, scatters, granulates, by spraying, fogging, dusting, watering. The application forms of the compositions are entirely guided by the purposes of use; in any case, they are intended to ensure the finest possible distribution of the active compounds according to the invention.

Medium to high boiling mineral oil fractions, such as kerosene or diesel oil, tar oils, etc., as well as oils of vegetable or animal origin, aliphatic, cyclic and cyclic, are suitable for the preparation of sprayable solutions, emulsions, pastes and oil dispersions. aromatic hydrocarbons such as benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or derivatives thereof such as methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, lsophorone etc., strongly polar solvents such as dimethylformamide, dimethylsulfoxide, N-methylpyrrolidone, water, etc.

Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders or oil dispersions by the addition of water. For the preparation of emulsions, pastes or oil dispersions, the substances as such or dissolved in oil or solvents can be homogenized with wetting agents, adhesives, dispersants or emulsifiers in water. However, concentrates consisting of the active ingredient, wetting agent, adhesive, dispersant or emulsifier and, optionally, solvent or oil, which are suitable for dilution with water, can also be prepared.

Surfactants include: alkali metal, alkaline earth metal, and ammonium salts of lginine sulfonic acid, corresponding naphthalenesulfonic acid, phenol sulfonic acid salts, alkylarylsulfonates, alkyl sulfates, alkyl sulfonates, alkali metal dibutylnaphthalenesulfonic acid salts, alkaline earth metal sulfates, lauryl sulfates alcohols, further alkali metal and alkaline earth metal fatty acid salts, sulfated hexadecanols, heptadecanols, octadecanols, sulfated glycol ethers of fatty alcohols, condensates 198173 start with sulphonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene and phenol naphthalenes , polyoxyethylenoctylphenol ethers, ethoxylated lspoctylphenyl, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, k by-products of fatty alcohols with ethylene oxide, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin, sulphite waste liquors and methylcellulose.

Powders, dusts and dusts may be made by mixing or. by comminuting the active ingredients with a solid carrier.

Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers. Solid carriers are, for example, mineral clays such as silica gel, silicic acids, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bolus, loess, clay. dolomite, diatomaceous earth, calcium sulphate and magnesium sulphate, magnesium oxide, ground plastics, fertilizers such as ammonium sulphate, ammonium phosphate, ammonium nitrate, ureas and plant products such as cereal flour, tree bark flour, wood flour and flour nut shell, powdered cellulose and other solid carriers.

The compositions according to the invention contain between 0.1 and 95 wt. % of active ingredient, preferably between 0.5 and 90% by weight;

Oils of various types of surfactant or adhesives, herbicides, fungicides, nematocides, insecticides, bactericides, trace elements, fertilizers, antifoams (e.g. silicones) may be added to the mixtures or to the individual active ingredients, growth regulators, antidotes or other herbicidally active compounds such as substituted alkylsulfonylglycolamides and -imides, substituted alkylaminosulfonylglycolamides and -imides, substituted acetanilidoalkylsulfites, substituted anilines, substituted azides, substituted aryloxycarboxylic acids, aryloxythlokarboxylic acids. acids and their salts, esters, amides and thioamides, substituted alkanols and alkenols, substituted ethers, substituted arsonic and arsenic acids, and their salts, esters and amides, substituted benzenesulfonamides, substituted benzimidazoles, substituted benzisothiazoles, substituted dihydrobenzofuranylalkylaminosulfonates, Benzthiadiazinone dioxides, substituted benzoxazines, substituted benzoxazinones, substituted benzoxazolinthiones, substituted benzthiadiazoles, substituted benzthiazolinyl alkylcarboxylic acids and their salts,. esters and amides, substituted biurets, substituted quinolines, substituted carbamates, substituted aliphatic or cycloaliphatic carboxylic or thiocarboxylic acids and their salts, esters and amides, substituted aromatic carboxylic and thiocarboxylic acids, and their salts, esters and amides, x substituted carbamoylalkylthiol- or -dithiophosphates, substituted quinazolines, substituted cycloalkylamidothiol carboxylic acids and their salts, esters and amides, substituted cycloalkylcarboxamidothiazoles, substituted dicarboxylic acids, and their salts, esters and amides, substituted dihydrobenzofuranylsulfides, substituted dihydrobenzofuranylsulfides dioxanes, substituted dipyridylium salts, substituted dithiocarbamates, substituted dithiophosphoric acids and their salts, esters and amides, substituted fluorocarboxylic acids and their salts, es ery and amides substituted ureas substituted hexahydro-carbothioate substituted hydantoins substituted hydrazides substituted hydrazonium salts, substituted hydrofuranony substituted _{isooxazolpyrimidony,:} substituted imidazoles, substituted imidazolindikarboxamidy substituted isothiazolpyrimidony, substituted ketones, substituted naphthoquinones, anhydrides substituted naftalových acids , substituted aliphatic hitriles, substituted aromatic nitrites, substituted oxadiazoles, substituted oxadiazolinones, substituted oxadiazinones, substituted oxadiazolines, substituted oxadiazolidinediones, substituted oxadiazinediones, substituted oxazolpyrimidones, substituted phenols, and their · salts and esters, substituted their phosphonic acids salts, esters and amides, substituted phosphonium chlorides, substituted phosphonalkylglycines,

19817 3 substituted phosphates, substituted phosphoric acids and their salts, esters and amides, substituted piperidines, substituted pyrazoles, substituted pyrazolalkylcarboxylic acids and their salts, esters and amides, substituted pyrazole salts, substituted pyrazolium alkyl sulfates, substituted pyridazines, substituted pyrldazones, substituted pyridine carboxylic acids as well as their salts, esters and amides, substituted pyridines, substituted pyridine carboxylates, substituted pyridirions, substituted pyrimidines, substituted pyrimidines, substituted pyrrolidinecarboxylic acids, and their salts, esters and amides, substituted pyrrololidines, substituted pyrrolidones, substituted arylsulfonic acids , as well as 1 salts, esters and amides thereof, substituted sulfamates, substituted styrenes, substituted sulfonyltoluides, substituted tetrahydrooxadiazoles, substituted tetrahydrooxadiazoldions, other tetrahydromethanoindenes, substituted tetrahydrodiazolthiones, substituted tetrhydrothiadiazinthiones, substituted tetrahydrothiadiazoliones, substituted aromatic thiocarboxamides, substituted thiobenzamides, substituted thiocarboxylic acids, and their salts, esters and amides, substituted thiolcarbamates, substituted thiocarbamates, substituted thiocarbamates, substituted thiocarbamates, substituted thiocarbamates, amides, substituted triazines, substituted triazinones, substituted triazoles, substituted uracils, substituted uretldinediones, chlorates, substituted azetldinecarbothloates, optionally also just prior to use.

The above-mentioned herbicidal compounds can also be applied before or after application of the individual active compounds or active compound mixtures according to the invention.

Admixture of these compositions with the herbicides according to the invention can be carried out in a weight ratio of 1:10 to 10: 1. The same applies to oils, wetting agents, or adhesives, fungicides, nematicides, insecticides, bactericides, antidotes and growth regulators.

The compositions according to the invention may be applied, inter alia, one or more times, before planting, after planting, before sowing, before emergence (preemergence), after emergence (postemergence) or during emergence of crop or undesirable plants.

The amount of compositions according to the invention used may vary and depends mainly on the type of effect desired.

The consumption is generally between 0.1 and 15 kg or more of active ingredient per hectare, preferably between 0.2 and 6 kg of active ingredient per hectare.

The compositions of the invention may be used in crops such as oats (Avena spp.), Wheat (Triticum spp.), Barley (Hordeum spp.), Rye (Secale spp.), Sorghum (Sorghum), corn (Zea mays). , millet (Panic mlliaceum) and rice (Oryza spp.), and in dicotyledonous cultures such as: crucifers (Cruclfereae), such as mustard (Brassica spp.), mustard (Sinapis spp.), radish (Raphanus spp.), watercress (Lepidium spp.), Compositae, for example. salad (Lactuca spp.), sunflower (Helianthus spp.), safflower (Carthamus spp.) ,. Scorzonera spp., Malvaceae, for example Gossypium hirsutum, Leguminosae, for example Medicago spp., Trifolium spp., Phaseolus beans. spp.), peanuts (Arachis spp.), soya (Glycine max), goosefoot (Chenopodlaceae), such as beet (Beta spp.), spinach (Spinacia spp.), aubergines (Solanaceae), such as aubergine (Solanum spp.), tobacco (Nicotiania spp.), capsicum (Capsicum annuum), flax (Linaceae), for example flax (Linum spp.), carrot (Umbelliferae), for example, parsley (Petroselinum spp.), carrot (Daucus carota), celery (Apium graveolens j, Rosaceae), such as strawberry (Fragaria), cucurbitaceae, such as cucumber (Cucumis spp.), Gourd (Cucurbita spp.), Lily (Liliaceae), such as garlic (Allium spp.), Vine (Vitaceae), such as grape vine (Vitis vlnifera), pineapple (Bromeliaceae), e.g. Ananas (Pineapple satlvus).

Example 1 (1)

Propionic acid 3,5-dichloro-4-methoxyanilide

19.2 g of parts by weight of 3,5-dichloro-4-methoxyaniline are stirred at 100 DEG C. for one hour with 26 parts of propionic anhydride, then the reaction mixture is cooled and added to 250 parts of ice-water with stirring. The precipitate is filtered off with suction and recrystallized from a mixture of ethanol and water to give 20 parts of the desired product, m.p. 137-139 ° C.

The following compounds were prepared in an analogous manner:

(2)

Propionic acid 3,5-dichloro-4-ethoxyanilide, m.p. 139-141 ° C, (3)

Propionic acid 3,5-dibromo-4-methoxyanilide, m.p. 132-134 ° C.

Example 2 (4)

2-methylvaleric acid 3,5-dichloro-4-methoxyanilide

To a solution of 192 parts of 3,5-dichloro-4-methoxyaniline and 103 parts of triethylamine in 1000 parts. 135 parts of α-methylvaleric acid chloride were added dropwise at 15 ° C, and the mixture was stirred at room temperature for 3 hours and then at 50 ° C for 1 hour. The reaction mixture is cooled, the precipitated triethylamine hydrochloride is filtered off with suction, washed with 200 parts of benzene and the combined filtrates are washed with water and 10% by weight, sodium carbonate solution. The benzene was distilled off in vacuo and the residue was recrystallized from a mixture of ethanol and water. 255 parts of the desired product are obtained, m.p. 72-74 ° C.

The following compounds were prepared in an analogous manner to the previous example:

(5)

Cyclopropanecarboxylic acid 3,5-dichloro-4-methoxyanilide, m.p. 167-169 ° C, (6)

Isobutyric acid, 3,5-dichloro-4-methoxyanilide, m.p. 105 DEG-107 DEG C. (7)

2-methylvaleric acid 3,5-dichloro-4-ethoxyanilide, m.p. 90-91 ° C, (8)

2-methylvaleric acid 3,5-dibromo-4-methoxyanilide, m.p. 109-111 ° C; (9)

Cyclopropanecarboxylic acid 3,5-dichloro-4-ethoxyanilide, m.p. 155-157 ° C, (10)

Cyclopropanecarboxylic acid 3,5-dichloro-4-methoxyanilide, m.p. 153-155 ° C; (U)

Isobutyric acid 3,5-dichloro-4-ethoxyanilide, m.p. 140-141 ° C, (12) ´

Isobutyric acid 3,5-dibromo-4-methoxyanilide, m.p. 180-183 ° C, (13)

145 DEG C., 3,5-dichloro-4-methoxyanilide, chloroacetic acid.

(14)

Bromoacetic acid 3,5-dichloro-4-methoxyanilide, m.p. 124-125 ° C, (15)

Dichloroacetic acid 3,5-dichloro-4-methoxyanilide, m.p. 154-155 ° C, (16)

Dichloroacetic acid 3,5-dibromo-4-methoxyanilide, m.p. 173 ° C, (17)

3,5-dichloro-4-methoxyanilide acid

2-chloropropionic melting point 120 ° C, (18)

3,5-dichloro-4-methoxyanilide acid

3-chloropropionic melting point 118 ° C, (19)

3,5-dichloro-4-methoxyanilide of butyric acid, m.p. 85 ° C, (20)

3,5-dichloro-4-methoxyanilide acid

4-chlorobutyric acid, m.p. 75 ° C;

Italy (21)

Pivalic acid 3,5-dichloro-4-methoxyanilide of melting point 145 ° C, (24)

Propionic acid 3-chloro-5-bromo-4-methoxyanilide, m.p. 136 ° C, (25)

Isobutyric acid 3-chloro-5-bromo-4-methoxyanilide, m.p. 128 ° C, (26)

Cyclopropanecarboxylic acid 3-chloro-5-bromo-4-methoxyanilide, m.p. Celsius.

The selective herbicidal activity of the active compounds according to the invention results from the following examples. Particularly important is the very good compatibility of these compounds for grain and cotton. Even particularly resistant weeds can be destroyed by the high doses of the compounds described, which they tolerate grain and cotton without significant damage.

Example 3

Plants of rice (Oryza sativa), wheat (Triticum aestivum), cotton (.Gossypium hirsutum), hedgehogs (Echinochloa crus galii), field fox (Alopecurus myosuroides), ryegrass (Lolium multiflorum), mustard (Sinap) Stellaria media, grown in a greenhouse, are treated at a dose of 2 kg / ha each with a height of 3 to 20 cm with active substances (1) =

Propionic acid 3,5-dlchloro-4-methoxyanilide (4) =

3,5-dichloro-4-methoxyanilide

2-methylvaler (5) =

Cyclopropanecarboxylic acid 3,5-dichloro-4-methoxyanil (6) =

Isobutyric acid 3,5-dichloro-4-methoxyanilide, and for comparison a dose of 2 kg / ha of the active substance (22) = -

3,4-dichloroaniline propionic acid, each dispersed in 500 l of water per hectare.

After two to three weeks, it was found that the active ingredients (1), (4), (5) and (6) showed better tolerability for crop plants with a stronger herbicidal effect than the comparative active ingredient (22).

The results obtained are shown in the following table using a scale of 0 to 100, where 0 means no damage and 100 represents complete destruction of the plants.

Table active substance (1) (4) (5) (8) (22)

Utility plants:

Oryza sativa 5 5 7 8 10 Triticum aestivum 5 5 0 and 15 Dec Gossypium hirsutum 10 10 10 0 35 Undesirable plants: Echinochloa crus-galli 70 70 95 90 50 Alopecurus myosuroides 70 75 80 85 80 Lolium multiflorum 60 70 75 75 40 Sinapis arvensis 100 ALIGN! 95 100 ALIGN! 100 ALIGN! 80 Stellaria media 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN! 90

Example 4

The test vessels in the greenhouse are filled with clayey soil and sewn with seeds of rice (Oryza sativa), soy (Glycine max.), Cotton (Gossypium hirsutum), corn (Zea mays), ryegrass (Lolium multiflorum), bedstraw (Galium aparine) and mustard (Sinapis arvensis). Immediately thereafter, treatment with the active substance (5) =

Cyclopropanecarboxylic acid 3,5-dichloro-4-methoxyanilide and, for comparison, the active substance (22) =

3,4-dichloroanilide propionic acid, each dispersed in 500 l of water per hectare. The active substance consumption is always 2 kg / ha.

After 4 to 5 weeks, it is found that the active compound (5) exhibits a better herbicidal effect than the active compound (22) with the same plant-tolerability.

The results are shown in the following table using a scale of 0-100, where 0 means no damage and 100 represents complete destruction of the plants.

¹⁸

Table active substance (5) (22) useful plants:

Oryza Sativa Glyclne max.

Gossypium hirsutum Zea mays unwanted plants: Lolium multiflorum Galium aparine Sinapis arvensls

EXAMPLE 5 parts by weight of compound (1) are mixed with 10 parts by weight of N-methyl-.alpha.-pyrrolidone to give a solution which is suitable for application as small droplets.

Example 6 parts by weight of compound (4) are dissolved in a mixture consisting of 80 parts by weight of xylene, 10 parts by weight of the addition product of 8 to 10 moles of ethylene oxide per 1 mol of N-monoethanolamine oleate, 5 parts by weight of calcium dodecylbenzenesulfonic acid; parts by weight of the addition product of 40 moles of ethylene oxide per mole of castor oil. By pouring and finely distributing the solution in 100,000 parts by weight of water, an aqueous dispersion is obtained which contains 0.02% by weight. % active substance.

Example 7 parts by weight of compound (5) are dissolved in a mixture consisting of 40 parts by weight, parts by weight of cyclohexanone, 30 parts by weight, isobutanol, 20 parts by weight, 7 parts ethylene oxide adduct per 1 mol isooctylphenol and 10 parts by weight ethylene oxide per mole of castor oil. By pouring and finely distributing the solution in 100,000 parts by weight of water, an aqueous dispersion is obtained which contains 0.02% by weight. % active substance.

EXAMPLE 8 parts by weight of compound (6) are dissolved in a mixture consisting of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction of boiling point 210 DEG-280 DEG C. and 10 parts by weight of an adduct of 40 moles of ethylene oxide. mol of castor oil. By pouring and finely distributing the solution in 100,000 parts by weight of water, an aqueous dispersion is obtained which contains 0.02% by weight. % active substance.

Example 9.

parts by weight of active ingredient (1) are mixed well with 3 parts by weight of diisobutylnaphthalene-α-sulphonic acid sodium salt, 17 parts by weight of ligninsulphonic acid sodium salt from waste sulphite lyes and 60 parts by weight of powdered silica gel and the resulting mixture is milled hammer mill. By finely distributing the mixture in 20,000 parts by weight of water, a spray suspension is obtained which contains 0.1% by weight of water. % active substance.

Example 10 parts by weight of compound (4) are intimately mixed with 97 parts by weight of finely divided kaolin. In this way, a dust containing 3 wt. % active substance·

Example 11 parts by weight of compound (5) are intimately mixed with a mixture of 92 parts by weight of powdered silica and 8 parts by weight of paraffin oil which has been sprayed onto the surface of the silica gel. In this way, an effective formulation with good adhesion is obtained.

Example 12

Various greenhouse plants are treated with the active ingredients (1), (4), (5), (6) and (9) after reaching a height of 9 to 18 cm, and, for comparison, with the active ingredient (23) 3-chloro-4- propionic acid methoxyanilide, always dispersed or emulsifiable in 500 l of water per hectare.

During the duration of the experiment, the plants are kept under considerably dry conditions. After two to three weeks, it is found that the active compounds (1) to (9) exhibit a better tolerability for crop plants than the active substance (23) with a somewhat stronger herbicidal action.

The results of the experiment are shown in the following table using a scale of 0-100, where 0 means no damage and 100 represents complete destruction of the plants.

о О О © ° о т-Ч СО со

о о т О о о гЧ К со LO

oo o "

со со

то т

Xt * (М оч ют о со со со

а то т о со со WITH о о о Т— < О О т т 00

Example 13

The various plants grown in the greenhouse are treated with an active substance I = 3,5-dichloro-4-methoxyanilide propionic acid, dispersed in 500 l of water per hectare, after reaching a height of 8 to 13 cm. The active substance consumption is 4.0 kg / ha.

After three to four weeks, it is found that the active compound I exhibits a strong herbicidal action with good tolerance to the crop plant.

The results of the experiment are shown in the following table using a scale of 0-100, where 0 means no damage and 100 represents complete destruction of the plants.

Table active ingredient dose kg / ha 4.0.0 crop plant

Zea mays0 unwanted plant

Sinapis alba100

The test results indicated that the active ingredient can be used to control undesirable broadleaf plant species in grass cultures.

Example 1 a d 14

Various plants grown in a greenhouse are treated with an active substance after reaching a height of 6-12 cm

IV = ’

2-methylvaleric acid 3,5-dichloro-4-methoxyanilide, emulsified in 500 L of water per hectare. The active substance consumption is 1.0 kg / ha.

After 3 to 4 weeks, it is found that the active compound IV exhibits a strong herbicidal effect with good tolerance to crop plants.

The test results are shown in the following table using a 0-100 scale, where 0 means no damage and 100 represents complete destruction of plants.

Table active ingredient IV 'dose kg / ha 1.0

The test results show that undesirable broadleaf plant species in grass cultures (Gramineae) can be controlled by the active ingredient.

Example 1 a d 15

Various plants grown in the wild are treated with an active substance I = 3,5-dichloro-4-methoxyanilide propionic acid at a rate of 3.0 kg / ha, dispersed in 500 l of water per hectare, after reaching a height of 1 to 15 cm. 2 1 wetting agents. During the experiment the precipitation amounts to 8 - 9 mm.

After three to four weeks, the following is ascertained:

The active substance I shows a good to very good action against broadleaf weeds such as Chenopodium album, Galinsoga parviflora, Matricaria chamomilla, Stellaria media and Sinapis árvensis. The effect against Amaranthus retroflexus a., Especially against Galium aparine (bedstraw) is much less. The degree of damage to unwanted grasses is considerable. The crop plant (rice - Oryza sativa) is practically not damaged at all.

The result of this field trial indicates the suitability of the active ingredient I for controlling broadleaf weeds in grass crops (Gramineae).

An adduct of 6-7 moles of ethylene oxide per mole of isooctylphenol is used as wetting agent.

The results of the experiment are shown in the following table using a scale of 0-100, where 0 means no damage and 100 represents complete destruction of the plants. The number of attempts is always shown in brackets for each value, and the value is an average value.

crop plant

Zea mays unwanted plant:

Sinapis alba 100

Table active substance dose kg / ha

AND

3.0

useful plant:, Oryza sativa 3.3 (3) undesirable plants: Alopecurus myosuroides 78 (3) Avena fatua 51 (3) Echinochloa crus galii 82 (2) Amaranthus retroflexus 78 (3) Chenopodium album 100 ALIGN! (3) Galinsoga parvlflora 96.6 (3) Galium aparine 40 (3) Matricaria chamomílla 92.5 (2) Stellaria media 90 (3) Sinapis arvensis 96.6 (3) Example 16 niche is after dosi

Various experimental plants grown in 5-20 cm glass slides are treated with the following active substances:

R ¹ -NH-C-R ²

II o

Ri

R ²

Cl

C2H5

СНз

I —CH — СНг — СНг — СНз

Cl

IV C2H5 Cl v řhXwá Cl C2H5

188173

Active substance . are applied • always emulsified or suspended in 500 liters of water per hectare. The test plants are divided according to species into individual test plants. and during the experiment they are well irrigated.

V. The following table gives information on the concentrations of test compounds, · the species of test plants used and their reactions · to the active substances tested three weeks after. treatment. The results are reported on a scale of 0 to 100, where it means no damage and 100 represents complete destruction of the plants. '

The results in this table show that the compounds of the invention have a better effect against undesirable broadleaf plants than the known active compounds. substances. It tolerates '' flesh '' for 'cultural plants'. (Oryza sativa, Zea mays) is similar: the effect against unwanted grasses is either the same (compound II) or weaker (compounds I and III) than for the comparators.

active substance dose kg / ha

Claims (1)

SUBJECT OF THE INVENTION A herbicidal composition comprising a solid or liquid carrier and an active compound-substituted anilide of the formula I in which: R1 is methyl or ethyl, R 2 represents a halomethyl, ethyl, halogenenethyl, propyl, halopropyl, butyl, halobutyl, pentyl or cyclopropyl group, the radicals containing 3 to 5 carbon atoms being straight or branched, and X is chlorine or bromine.