IL45758A - N-substituted o-(dialkylaminosulfonyl)-glycolanilides - Google Patents

Abstract

1476219 O - (Disubstituted aminosulphonyl)- glycolic anilides BASF AG 15 Oct 1974 [15 Oct 1973] 44585/74 Heading C2C The invention comprises compounds of Formula I in which R<SP>1</SP> and R<SP>2</SP> each denote alkyl, haloalkyl or cycloalkyl, R<SP>3</SP> denotes alkyl, cycloalkyl, alkenyl, cycloalkenyl or substituted or unsubstituted benzyl and X and Y each denotes hydrogen, alkyl, alkoxy, haloalkyl, or halogen which may be prepared by reacting a substituted glycolic anilide with a dialkyl aminosulphonyl halide. Herbicidal compositions comprise a compound of Formula I together with a solid or liquid carrier. [GB1476219A]

Description

45758/2 N-S bstituted 0-(dialkylaminosulfonyl)- glycol-anilides BASF AKTIENGESELISCHAFT C? 43776 45758/2 This Invention relates to new and valuable li-substituted 0-(dialkylaminosulfonyl)-glyeolanilides, herbicides containing these compounds, and a process for controlling the growth of unwanted plants with these compounds.

It is known (German Paten 1,OH,380) to use 2-chloro-N-ieopropyiace ic acid anilide as herbicide. However, its herbi-cidal action is onl poor. It is si¾o known (German Laid-Qpen Application DCS 2,201,432) to use 0~( lk laminon lfonyl)-glyoolaiiilidea aa herbicides. Eowever, their herbicidal action is only poor.

We have new found tha li-substituted 0-(dialkylamino-sulfonyl)-glycolanllides of the formula where R and fi 2 each denote alkyl or haloalkyl, R denotes alkyl or alkenyl, and X and T each denote hydrogen, alkyl, alkoxy, haloalkyl or halogen, have a better herbicidal action than the prior art active ingredients. 1 2 " Examples of meanings for B and B are methyl, ethyl, propyl, isopropyl, butyl and a-chloroethyl. 3 B may for instance denote methyl, ethyl, propyl, isopropyl, butyl, iscbutyl, sec-butyl, tert-butyl, pentyl, hexyl, allyl, butenyl, pentenyl and hexenyl.

X and Y may for instance denote methyl, ethyl, propyl, isopropyl, met.hoxy, ethoxy, fluoro, chloro, bromo, iodo and tri lttoromethyl.

The ne¾ 0-(dialkylamin6sulfonyl)-glycolanilides may for instance be- prepared by reacting a substituted glycolic acid anilide with an appropriatel ■ substituted aminosulfonyl balide. If desired, the anilide sa be employed as aleoholate.

The preparation of the compounds of the invention is illustrated by the following Example. 2XAMPLE 1 Q-(diaeth laminosulfon.yl)~N~isoprop.yl glycolic acid anilide A 20° to 30°G and at the rate at which hydroge ¾as evolved, a solution of 38.6 parts of N-isopropyl glycolic acid anilide in 60 parts of tetrahydrofuran waa added to a suspension of 4·8 parts of sodium hydride in 100 parts of tetrahydrofuran. After the mixture had reacted for a further hour at 40°C, 36 parts of dlmethylaminosulfonyl chloride was metered in at 5°C. The mixture was allowed to stand overnight. Subsequently, the solvent and unreacted dimethylaminosulfonyl chloride were dis tilled off in vacuo (0.1 mm) at a temperature of up to 60°C. The oily residue was dissolved in 250 parts of benzene and treated in turn wi hydrochloric acid, water, dilute sodium bicarbonate solution and again with water. The organic phase was dried with magnesium sulfate and concentrated in vacuo. The residue crystallized upon treatment with a mixture of diisopropyl ether and ligroin. The crude product was recrystallized from diisopropyl ether. Melting point: 64° to 65°C<, The compound has the following structural formula: The compounds listed in the following tabl prepared analogously: R' m.p. (°C) m.p. (°C) methyl 64 to 66 methyl ethyl 58 to 59 ethyl propyl propyl butyl isopropyl 64 to 65 isobutyl butyl sec-butyl 47 to 48 isobutyl tert-butyl sec-butyl allyl tert-butyl allyl O.Z. 30,141 methyl methyl ethyl ethyl propyl propyl isopropyl 1.5202 Isopropyl butyl butyl isobutyl isobutyl sec-butyl sec-butyl tert-butyl tert-butyl allyl allyl methyl methyl ethyl ethyl propyl propyl isopropyl isopropyl butyl butyl isobutyl isobutyl sec-butyl sec-butyl tert-butyl tert-butyl - \ - R' methyl methyl ethyl ethyl propyl propyl isopropyl isopropyl butyl butyl isobutyl Isobutyl sec-butyl sec-butyl tert-butyl tert-butyl allyl allyl benzyl benzyl methyl methyl ethyl ethyl propyl propyl isopropyl isopropyl butyl butyl isobutyl isobu yl sec-butyl sec-butyl O.Z. 30,1 1 tert-butyl tert-butyl allyl allyl methyl methyl ethyl ethyl propyl propyl isopropyl Isopropyl butyl butyl lsobutyl lsobutyl sec-butyl sec-butyl tert-butyl tert-butyl allyl allyl Application may be effected for Instance In the form of directly sprayable solutions, powders, suspensions, dispersions, emulsions, 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 a fine distribution of the active ingredient.

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, etc. and oils of vegetable o l^- animal origin, aliphatic, cyclic and aromatic hydrocarbons such as benzene, toluene, xylene, paraffin, tetrahydronaph- thalene, 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 di-methylformamide, dimethyl sulfoxide, 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 sol-vent 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 dibutylnaphthalenesulfonlc acid, 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 ether, 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 isooctyl-phenol, 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 polyoxypropyl-ene, 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 silica gel, silicic acid, 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.

There may be added to the compositions or individual active ingredients (if desired, immediately before use (tank-mix)) oils of various types, herbicides, fungicides, nemato-cides, insecticides, bactericides, trace elements, fertilizers, antifoams (e.g., silicones), growth regulators, anti- dotes and other herbicldally effective compounds such as r substituted anilines substituted aryloxycarboxylic acids and salts, esters and amides thereof substituted ethers substituted arsonic acids and their salts, esters and amides substituted benzimidazoles substituted benzisothiazoles substituted benzothiadiazinone dioxides substituted benzoxazines substituted benzoxazinones substituted benzothiadiazoles substituted biurets substituted qulnolines substituted carbamates substituted aliphatic carboxyllc acids and their salts, esters and amides substituted aromatic carboxyllc acids and their salts, esters and amides substituted carbamoylalkylthiol- or -dithiophosphates substituted quinazolines carbox substituted cycloalky^midocarbothiolic acids and their salts, esters and amides substituted cycloalkylcarboxamidothiazoles substituted dicarboxylic acids and their salts, esters and amides substituted dihydrobenzofuranyl sulfonates substituted disulfides substituted dipyridylium salts substituted dithiocarbamates substituted dithiophosphoric acids and their salts, esters and amides substituted ureas azepine substituted hexahydro-lH7fcarbothipates substituted hydantoins substituted hydrazides substituted hydrazonium salts substituted isoxazole pyrimidones substituted imidazoles substituted isothiazole pyrimidones substituted ketones substituted naphthoquinones substituted aliphatic nitriles substituted aromatic nitriles substituted oxadiazoles substituted oxadiazinones substituted oxadiazolidine diones substituted oxadiazine diones substituted phenols and their salts and esters substituted phosphonic acids and their salts, esters and amides substituted phosphonium chlorides o substituted phosphonAlkyl glycines substituted phosphites substituted phosphoric acids and their salts, esters and amides substituted piperidines substituted pyrazoles substituted pyrazole alky1carboxyllc acids and their salts, esters and amides substituted pyrazolium salts substituted pyrazolium alkyl sulfates substituted pyrldazines substituted pyridazones substituted pyridine carboxyllc acids and their salts, esters and amides substituted pyridines substituted pyridinones substituted pyrimidines substituted pyrimidones substituted pyrrolidine carboxyllc acid and its salts, e sters and amides substituted pyrrolidines substituted pyrrolidones substituted arylsulfonic acids and their salts, esters and amides substituted styrenes substituted tetrahydroxadiazine diones substituted tetrahydromethanoindenes substituted tetrahydroxadiazole thiones substituted tetrahydrothiadiazine thiones substituted tetrahydrothiadiazole diones substituted aromatic thiocarboxamides substituted thio'carboxylic acids and their salts, esters and amides substituted thiol carbamates r substituted thioureas substituted thiophosphoric acids and their salts, esters and amides substituted triazines substituted triazoles substituted uracils, and substituted uretidine diones.

The last-mentioned herbicidal compounds may also be applied before or after the active ingredients or compositions thereof according to the invention.

These agents may be added to the herbicides according to the invention in a ratio by weight of from 1 : 10 to 10 : 1. The same applies to oils, fungicides, nematocides, insecticides, bactericides, antidotes and growth regulators.

The amount used of the agents according to the invention may vary and depends in essence on the type of effect to be achieved; it is generally from 0.1 to 15 (and more), preferably from 0.2 to 6, kg per hectare of active ingredient. The agents according to the invention may be applied once or several times before or after planting, before sowing, and before, during or after emergence of the crop plants and unwanted plants.

The new compositions have a strong herbicidal action and may therefore be used as weedkillers or for controlling the growth of unwanted plants. Whether the new active ingredients are used as total or selective agents depends in essence on the amount of ingredient used per unit area.

By weeds and unwanted plant growth are meant, all mono- Ο.Ζ. 30,] 1 cotyledonous and dicotyledonous plants which grow in loci where they are not desired.

The agents according to the invention may therefore be used for controlling for instance Gramineae, such as Cynodon spp. Dactylis spp.

Digitaria spp. Avena spp.

Echinochloa spp. Bromus spp.

Setaria spp. Uniola spp.

Panicum sp o Poa spp.

Alopecurus spp. Leptochloa spp.

Lolium spp. Brachiaria spp.

Sorghum spp. Eleusine spp.

Agropyron spp. Cenchrus spp.

Phalaris spp. Eragrostis spp.

Apera spp. Phragmites communis Cyperaceae, such as Carex spp. Eleocharis Cyperus spp. Scirpus spp etc. ί dicotyledonous weeds, such as Malvaceae, e.g.

Abutilon theoprasti Hibiscus Sida spp. Mal a spp Compositae, such as Ambrosia spp. Centaurea spp.

Lactuca spp. Tussilago spp.

O.Z. 30,141 Senecio spp. Lapsana communis Sonchus spp „ Tagetes spp.

Xanthium spp. Erigeron spp.

Iva spp. Anthemis spp.

Galinsoga spp. Matricaria spp.

Taraxacum spp. Artemisia spp.

Chrysanthemum spp. Bidens spp.

Cirsium spp. etc.; Convolvulaceae, such as Convolvulus spp. Cuscuta spp.

Ipomoea spp. Jaquemontia tamnifolia etc, ί Cruciferae, such as Barbarea vulgaris Arabidopsis thaliana Brasslca spp. Descurainla spp.

Capsella spp. Draba spp.

Sisymbrium spp. Coronopus didymus Thlaspi spp. Lepidium spp.

Sinapis arvensis Raphanus spp. etc. ; Geraniaceae, such as Erodium spp. Geranium spp. etc. j Portulacaceae, such as Portulaca spp. etc .

Primulaceae, such as Anagallis arvensis Lysimachia spp. etc. j Rubiaceae, such as O.Z. 30,141 Richardia spp. Diodia spp.

Galium spp. etc , ; Scrophularlaceaej, such as Linaria spp. Digitalis spp.

Veronica spp.

Solanaceae, such as Ph salis spp. Nicandra spp.

Solanum spp0 Datura spp. etc o J Urticaceae, such as Urtica spp„ Violaceae, such as Viola spp.

Zygophyllaceae, such as Tribulus terrestris Euphorbiaceae, such as Mercurialis annua Euphorbia spp.

Umbelliferae, such as Daucus carota Ammi majus Aethusa cynapium Commelinaceae, such as Commelina spp, etc . ; Labiatae, such as Lamlum spp. Galeopsis spp. etc Leguminosae, such as Medicago spp. Sesbania exaltata Trifolium spp. Cassia spp.

Vicia spp. Lathyrus spp. o.z. 30,141 Plantaginaceae, such as Plantago spp.

Polygonaceae, such as Polygonum spp. Fagopyrum spp.

Rumex spp. ΘtC · J Aizoaceae, such as Mollugo verticillata etc . ; Amaranthaceae, such as Amaranthus spp. βtC i Boraginaceae, such as Amsinckia spp„ Anchusa spp.

Myostis spp. Li hospermum spp. etc . ; Caryophyllaceae, such as Stellaria spp. Silene spp.

Spergula spp. Cerastium spp.

Saponaria spp. Agrostemma githago Scleranthus annuus ΘtC Chenopodiaceae, such as Chenopodium spp. Atriplex spp.

Kochia spp. Monolepsis nuttalliana Salsola Kali etc . j Lythraceae, such as Cuphea spp. etc . ; Oxalidaceae, such as Oxalis spp.

Ranunculaceae, such as Ranunculus spp. Adonis spp.

Delphinium spp.

O.Z. 30,1 1 Papaveraceae, such as Papaver spp. Fumaria officinalis ΘtC o $ Onagraceae, such as Jussiaea spp.

Rosaeeae, such as Alchemillia spp. Potentilla spp.

Potamogetonaceae, such as Potamogeton spp. €t o Najadaceae, such as Najas spp. etc. ; Marsileaceae, such as Marsllea quadrifolia etc.

The new agents may be in cereal crops such Avena spp. Sorghum Triticum spp. Zea mays Hordeum spp. Panicum miliaceum Secale spp. Oryza spp. and in dicotyledon crops s' Cruciferae, e.g.

Brassica spp. Raphanus spp, Sinapis spp, Lepidium spp.

Compositae, e.g.

Lactuca spp. Carthamus spp.

Helianthus spp. Scorzonera spp, Malvaceae, e.g.

Gossypium hirsutum Leguminosae, e.g.

O.Z. 30,141 Medicago spp. Phaseolus spp.

Trifolium spp. Arachis spp.

Pisum spp» Glycine max.

Chenopodiaceae, e.g.

Beta vulgaris Spinacia spp.

Solanaceae, e.g.

Solanum spp. Capsicum annuum Nicotiana spp.

Linaceae, e.g.

Li'ium spp.

Umbelli erae, e.g.

Petroselinum spp. Apium graveolens Daucus carota Rosaceae, e.g. Fragaria Cucurbitaceae, e„g.

Cucumis spp, Cucurbita spp, Liliaceae, e.g.

Allium spp.

Vitaceae, e.g.

Vitis vinifera Bromeliaceae, e.g.

Ananas sa ivus.

EXAMPLE 2 In the greenhouse, loamy sandy soil was filled into pots and sown with the seeds of various plants. The soil prepared in this manner was then immediately treated with 1 kg/ha of each of the following active ingredients, each compound being dispersed or emulsified in 500 liters of water per hectare; I 0-(dimethylaminosulfonyl )-N-methyl glycolic acid a iljpie II 0-(dimethylaminosulfonyl)-N-isopropyl glycolic acid anilide III 0-(diethylaminosulfonyl )-N-isopropyl glycolic acid anilide IV 0-(dimethylaminosulfonyl )-N-sec-butyl glycolic acid anilide V 0-(dime hylaminosulfonyl)-N-ethyl glycolic acid anilide VI 0-(methyl- -chloroethylaminosulfonyl)-N-isopropyl glycolic acid anilide VII 2-chloro-N-isopropyl acetic acid anilide VIII 0-( 2'-propylaminosulfonyl)-N-ethyl glycolic acid anilide.

After 5 to 4 weeks it was ascertained that active ingredients I to VI had a better herbicidal action than compounds VII and VIII, combined with the same crop plant compatibility.

The results are given below: Active ingredient I II III IV V VI VII VIII kg/ha 1 1 1 1 1 1 1 1 Crop plants: Brassica napus (rape) 0 0 0 0. 0 0 0 0 Glycine hispida (soybeans) 0 0 0 0 0 0 0 0 Zea mays (Indian corn) 0 0 0 0 0 0 0 0 Beta vulgaris (beet) 0 0 0 0 0 0 0 0 Unwanted plants: Lolium multiflorum (Italian ryegrass) 90 80 78 75 86 80 20 73 O.Z. 30,1 1 Active ingredient I · II III IV V VI VII VIII Lolium perenne (perennial ryegrass) 80 75 72 70 80 7 20 64 Echinochloa crus-galli (barnyard grass) 100 90 8 80 95 95 20 75 Setaria faberii (giant foxtail) 90 85 80 80 85 90 25 75 Setaria viridis (green foxtail) 95 90 86 82 90 90 15 72 Poa trivialls (common bluegrass) 90 80 76 75 88 8 25 70 Poa annua (annual bluegrass) 100 9 90 85 95 95 25 78 0 = no damage 100 = complete destruction.

EXAMPLE 3 In the greenhouse, various plants were treated at a growth height of from 3 to 18 cm with 1 kg/ha of each of active ingredients I to VIII, each compound being dispersed or emulsified in 500 liters of water per hectare.

After to 4 weeks it was ascertained that active ingredients I to VI had a better herbicidal action than compounds VII and VIII, combined with the same crop plant compatibility.

The results are given below: Active ingredient I II III IV V VI VII VIII Crop plants: Brassica napus (rape) 0 0 0 0 0 0 0 10 Glycine hisplda (soybeans) 0 0 0 0 0 0 10 5 Zea mays (Indian corn) 0 0 0 0 0 0 0 5 O.Z. 30,141 Active ingredient I II III IV V VI VII VIII kg/ha 1 1 1 1 1 1 1 1 Beta vulgaris (beet) 0 0 0 0 0 0 5 0 Unwanted plants: Echinochloa crus-galli (barnyardgrass) 80 80 75 80 8 75 4° 80 Setaria faberii (giant foxtail) 80 78 75 80 75 75 10 85 Setaria viridis (green foxtail) 80 75 70 80 80 70 10 70 Poa trivialis (common ryegrass) 85 80 76 84 75 72 30 68 Lolium multiflorum (Italian ryegrass) 80 76 72 80 72 75 15 80 0 = no damage 100 = complete destruction.

EXAMPLE 4 90 parts by weight of compound I is mixed with 10 parts by weight of N-methyl-a-pyrrolidone. A mixture is obtained which is suitable for application in the form of very fine drops.

EXAMPLE 5 20 parts by weight of compound II 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 to 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 to 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 O.Z. 30,141 r 0.02% by weight of the active ingredient.

EXAMPLE 6 20 parts by weight of compound III 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 to 1 mole of isooctylphenol, and 10 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring the solution into 100, 000 parts by weight of water and uniformly distributing it thereir, an aqueous dispersion is obtained containing 0.02 by weight of the active ingredient.

EXAMPLE 7 20 parts by weight of compound IV is dissolved in a mixture consisting of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210° and 280°C, and 10 parts by weight of the adduct of 40 moles of ethylene oxide to 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.

EXAMPLE 8 20 parts by weight of compound V is well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-a sulfonic acid, 17 parts by weight of the sodium salt of a ligninsulfonlc acid obtained from a sulfite waste liquor, and 60 parts by weight of powdered silica gel, and triturated in a hammer mill. By uniformly distributing the mixture in 20, 000 parts by weight of water, a spray liquid is obtained containing 0.1$ by weight of the active ingredient.

O.Z. 30,141 ^ EXAMPLE 9 3 parts by weight of compound I is intimately mixed with 97 parts by weight of particulate kaolin. A dust is obtained containing by weight of the active ingredient.

EXAMPLE 10 30 parts by weight of compound II 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 t. e active ingredient is obtained having good adherence

Claims (1)

1. Q A substituted of the ormula where and denote alkyl or denotes or and X and Y each denote haloalkyl or A herbicide comprising ft of the formula where and denote alkyl or denotes and X and Y each denote alkyl A herbicide a solid liquid carrier and a of the where R and R each denote alkyl or denotes alkyl or and X and Y each denote haloalkyl or A process for producing a herbicide wherein a or liquid carrier is mixed with a of the formula 1 where and each denote or denotes and X and each denote haloalkyl or A process for controlling the growth of unwanted plants wherein plants or the soil treated a subetituted formula 3 where and each denote alkyl or denotes alkyl or and X and Y eaeh denote haloalkyl or A process producing a of the formul 3 where and each denote alkyl or denotes alkyl or and X and Y each denote haloalkyl or wherein a of the formula where Y and the above is reacted with a chloride of the formula 2 have above glycolic acid glycolic acid acid glycolic acid glycolic acid glycolic acid For the nts AND insufficientOCRQuality