DK142810B - O-ALKYLSULPHONYL-GLYCOLIC ACIDANILIDES FOR USE IN HERBICIDES - Google Patents

Description

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(11) EREMLCGGEUEmRIFT 11 + 28 1 0 DENMARK «1» in..c, .J c o? c U3 / 68 A 01 N 41/04 '(21) Application No 5001/74 (22) Filed on 24 Ββρ. 1 974 (24) Live 24 ββρ. 1974 (44) The application presented and the petition published on 2. f eb · 1 9 ^ 1

DIRECTORATE OF

PATENT AND TRADE MARKET <3 °) Priority requested from it

Oct 1 1975, 2549256, DE

(71) BASF AKTIENGESELLSCHAFT, Carl-Bosch-Straese 58, 67ΟΟ Ludwigs =

Hafen, DE.

(72) Inventor: Adolf Fischer, Deidesheitner Straese 4, 6704 Mutterstadt, DE: Hanspeter Hansen, Thorwaldsenstrapse 5, 67ΟΟ Ludwigshafen, DE:

Wolfgang Rohr, Gontardstrasse 4, 6800 Mannheim 1, DE.

(74) Plenipotentiary in the proceedings:

Hofman-Bang & Boutard Engineering Company.

(54) O-alkylsulfonyl-glycolic acids for use in herbicides.

This invention relates to novel valuable O- (alkylsulfonyl) glycolic acid anilides for use in herbicides.

It is known to use chloroacetic acid N-isopropyl anilide as herbicide (German Patent No. 1,014,380). It has little herbicidal activity.

Swiss Patent No. 477,161 also discloses certain glycolic acid derivatives which can be used as herbicides, but neither do they exhibit satisfactory herbicidal activity, as compared to the comparative test results set forth later in this specification.

2 142810

It is an object of the invention to provide an O- (alkylsulfonyl) glycolic acid anilide which exhibits a better herbicidal activity in relation to the known glycolic acid derivatives.

The O- (alkylsulfonyl) glycolic acid anilide according to the invention is characterized by the characterizing part of the claim, and it has surprisingly been found that these O- (alkylsulfonyl) glycolic acid anilides exhibit a superior to the known compounds mentioned above. herbicidal action.

The herbicidal action of the new compounds against weeds, including millet species, is excellent.

The new compounds can be prepared by various methods: I. By reaction of substituted F-chloromethyl-O-alkylsulfonyl-3-glycolic acid anilides with an alcohol R OH according to the following general reaction scheme:

Jl1 1 / - \ ^ H2-01 0H 0_r3 (oW "4 3 _H01 ° \ r / 0-0H2-0-S-a4 + R3QH riC V / .XC-CH - 0-S-R4" 0 o R oo 12 3 4 where R, R, R and R have the meaning given above.

The reaction is carried out in the presence of an acid-binding agent, whereby the alcohol is preferably used as an alkali alcoholate.

3 142810

The N-chloromethyl-O-alkylsulfonyl-glycolic acid anilides needed for this reaction can be prepared by addition of an O-alkylsulfonylglycolic acid chloride to N-methylene anilines.

2. In addition, the new compounds are prepared in accordance with the following general reaction scheme: R1 j-C GH-O-R3 S / -C .CH-O-R3 // 2 nl c p4 -HC1 / r \ 20

V- / C-CHo-OH-C-C-CH-O-O-S-R

\ 2 «^ u \ 2 ti * tt

Ro R o o 12 3 4 whereby R, R, R and R have the meaning given above.

This reaction is also preferably carried out in the presence of an acid binding agent.

For example, the substituted glycolic acid anilides needed for this reaction can be prepared by the following reactions: R1 / - \ / -r ch-ci (o M = 0H2 + 01 ° -0H2- ° - = - 0H3 ->

'-C p 0 0' -J ^ C-CHo '0-G-GH

Y \ 2 "2" 3 RO 0 rV / 0H201 5 / _ ^ sl CB2-o-r3 (oVx + 2NY _ * (oVv

\ _ / ^ O-OH.-O-O-OH, '7 \ _ / ^ C-0H.-0H

\ 2 »2" 5 \ h2 ”2 R 0 0 K 0 12 3 where R, R and R have the meaning given above.

Etherization to alkoxymethyl group and cleavage of the acetyl residue can thereby also be carried out in stages.

The method of preparation according to method 2, 4, 142810 is preferred

In order to compare the active compounds known from Swiss Patent No. 477,161 and compounds related to those of Swiss Patent No. 477,161 to the new compounds of the invention, the experiments set forth below were carried out.

The compounds examined were as follows.

Active ingredient no.

f * tl O

No. 3 CH CH patent no.

"C-CHp-O-S-CH, 477,161 (No. 62)" —f π 2 π> 0 0 2 (f "CH patent no.

\ - / XC-CH9-0-S-CH, 477-161 (No. 136) n ^ il -> 0 0 3 // \ v-Nx "CH patent specification no.

S-CH 2 O 0 C 2 H 5 477.161 (No. 137) 0 0, -v / CH 2 -O-CH, 4 // \ ^ - Ν q not described in \ = / C-CHo-0-S-CH-z patent specification no.

IN! 2 Li 3 477,161 0 0 f— ^ CHq — 0 — C-zELyi 5 // Yht ^ \ (not described in \ _ / \ ___ Λ J CH patent no.

C-CH2-0-S-CH3 477.16I

ch3 0 0 g f / The present invention CH-CHp-O-S-CH, invention \ II ^ It 3 CH3 0 0 7 to 17: present invention 142810 5

Most of the experiments were conducted in the greenhouse. Paraffinized paper cups with a volume of 200 cm 2 were used as containers, and the soil used was a sandy clay mound containing approx.

1.5% organic matter. The seeds of the experimental plants were then sown superficially, separated by species. The active ingredients were then applied immediately (pre-germination treatment). They were suspended or emulsified in water as a distribution agent and sprayed onto the surface of the soil through atomizer nozzles. After application of the agents, the containers were watered lightly and then covered with transparent plastic caps until the plants sprouted. As the experiments were conducted in the summertime, the temperatures ranged between 20 and 40 ° C. As a result, the species studied were almost exclusively thermophilic. The experimental period was between 3 and 6 weeks, during which time the plants were taken care of, watering them abundantly. Their reaction to the various treatments was observed. The active ingredients, the application intensities in kg of active ingredient / ha and the species of the test plants are given below. The plants were rated on a scale between 0 and 100, where 0 means no damage or normal germination and 100 means complete destruction or non-germination.

In addition, active constituents 4, 5 and 6 were studied outdoors in small plots. The soil was again a sandy clay containing small amounts of organic matter. Soybeans were sown as crop plants; the weeds were of the type usually found on the acreage. The product was applied after sowing and before the seedlings of the crops were sprouted, using a tractor equipped with spray equipment for the parcels. The compounds were again suspended or emulsified in water as a distribution agent. As no precipitation naturally occurred during the trial, the parcels were irrigated with sprinklers. The assessment method was the same as in the greenhouse trial.

The first series contained a group of compounds of the invention and a comparative compound (Table 2). There can be no doubt that the new compounds are effective active ingredients. They sometimes differ slightly in their activity towards unwanted plants. As a whole, the group is fairly uniform and clearly superior in terms of herbicidal activity relative to the comparison compound.

142810 6

The new compounds are well tolerated by a large number of crop plants, e.g. cotton and soybean.

Another group contained active ingredient # 6 as representing the invention, as well as Comparative Compounds 2, 3, 4 and 5 (Table 3). Also, in this case, the known or related compounds did not exhibit near as good herbicidal activity as the new active ingredient of the invention.

The field parcel experiments also showed the better herbicidal activity of the active ingredient # 6 in comparison with the very poor comparison compounds (Table 4).

It is clear from the experiments that the compounds of the invention exhibit a significantly better herbicidal activity than the known compounds.

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Examples 2 and 5 hereinafter refer to a process for the preparation of the compounds of the invention, Examples Nos. 1, 3 and 4 describe a process for preparing the intermediates of the compounds of the invention, Examples Nos. 6 and 7 deal with documentation of the herbicide. activity of the compounds of the invention, and Examples 8-14 deal with the preparation of compositions containing the active compounds of the invention.

Example 1 N-Chloromethyl-2,6-diethyl-O-methylsulfonyl-glycolic acid anilide

To a solution of 80.5 parts (parts by weight) of N-methylene-2,6-diethylaniline in 150 parts of ether was added with stirring at 0 to -3 ° C a solution of 86.5 parts of 0-methylsulfonyl-glycolic acid chloride. and 150 parts of ether. After stirring for 2 hours at 0 to 5 ° C, the reaction mixture was cooled to 0 ° C. The precipitated addition product was suctioned off, washed with cold ether and dried in a vacuum desiccator. The melting point was 105 to 107 ° C.

The compound has the following structural formula: / ° 2Η5 j- (CH Cl

S

\ - / X-CHo-0-S-CH, V ». 2 i · 3 c2h5 0 0 Similarly, one can make:

N-chloromethyl-2,6-dimethyl-O-methylsulfonyl-glycolic acid anilide, m.p. 69 to 70 ° G

N-chloromethyl-2-methyl-6-ethyl-O-methylsulfonyl-glycolic acid anilide, m.p. 80 to 82 ° C

O-methylsulfony1-glycolic acid chloride is known from U.S.A. U.S. Patent No. 3,200,138.

N-ethoxymethyl-2,6-diethyl-O-methylsulfonyl-glycolic anilide 13282810

Example 2

A sodium ethylate solution made of 9.2 parts of sodium and 250 parts of ethanol was added at 15 to 25 ° G to a solution of 153 »4 parts of N-chloromethyl-2,6-diethyl-O-methylsulfonyl-glycolic acid anilide in 400 parts ethanol. After stirring for 1 hour at room temperature, the precipitated sodium chloride was separated and the reaction solution was evaporated in vacuo. The residue was dissolved in 300 parts of acetic acid ethyl ester and shaken twice with water.

The organic solution dried with magnesium sulfate, by evaporation in vacuo, left a syrupy residue which crystallized slowly at room temperature: mp 38 to 41 ° C.

Crystallization of ether / petroleum ether mixture yielded the pure analyte: m.p. 43 to 44 ° C.

The compound has the following structural formula: AH5

, - / xCH 00 H

/ T \ / 2 2 5o

OK

\ _ / Nj-ch_-o-s-ch_ i? 2 '3 XC2H5 o o Similarly, one can make:

N-Methoxymethyl-2,6-diethyl-O-methylsulfonyl-glycolic acid anilide, m.p. 57 to 58 ° C

N-propoxymethyl-2,6-diethyl-O-methylsulfonyl-glycolic anilide, n 5 = 1,5115 N-isopropoxymethyl-2,6-diethyl-O-methylsulfonyl-glycolic anilide, n 2,6-diethyl-O-methylsulfonyl-glycolic anilide, n + 5 = 1.5080 N-isobutoxymethyl-2,6-diethyl-0-methylsulfonyl-glycolic anilide, n * 5 = 1.5085 14 142810

M-methoxyme thly-2,6-dimethyl-O-methylsulfonyl-glycolic anilide, m.p. 64 to 65 ° C

N-ethoxymethyl-2,6-dimethyl-O-methylsulfonyl-glycolic anilide, m.p. 60 to 62 ° C

N-propoxymethyl-2,6-dimethyl-O-methylsulfonyl-glycolic anilide, 45 = 1.5155 N-isopropoxymethyl-2,6-dimethyl-O-methylsulfonyl-glycolic anilide, 45 = 1.5130

W-Methoxymethyl-2-methyl-6-ethyl-O-methylsulfonyl-glycolic acid anilide, m.p .: 44 to 45 ° C

Example 3 N-Chloromethyl-2,6-diethyl-O-acetyl-glycolic acid anilide To a solution of 136.5 parts of acetoxyacetyl chloride in 150 parts of 0 ether (dry) was added at 0 ° C with stirring 161 parts of E-methylene-2,6-diethylaniline. dissolved in 250 parts ether. To complete the reaction, the mixture was stirred for 2 hours at 25 ° C. Then a little undissolved material was separated and the clear solution was evaporated in vacuo. After the addition of 250 parts of petroleum ether and cooling with ice water, the crystalline product was melted: m.p. 51 to 54 ° C. After repeated recrystallization with ether / p.etrol ether, the analyzed product had a melting point of 56 to 58 ° C.

The compound has the following structural formula: r- / oh 01 <0K 2 \ - (^ C-OHo-0-0-0H

N. I * ^ II J

C 2 H 5 o N-methoxymethyl glycolic acid 2,6-diethylanilide

Example 4

To a solution of 119 parts of N-chloromethyl-2,6-diethyl-O-acetyl-glycolic acid anilide in 400 parts of methanol was added, with stirring at 15 to 20 ° C, 131 parts of a 33 in (weight percent) solution of sodium methylate in methanol which was further diluted with 100 parts of methanol.

To complete the reaction, the solution was stirred for 15 hours at room temperature. For work up, the reaction mixture was neutralized and evaporated in vacuo. The residue was dissolved with acetic acid ethyl ester and washed twice with water. The organic solution was dried over magnesium sulfate and evaporated in vacuo. The syrupy residue was purified by distillation:

Kp0.05 120 U1 125 ° ° »nD5 = 1> 5255 ·

The compound has the following structural formula: C2H5 r ~ (^ h2-ooh3

-1-C-CH, OH

Similarly, N-ethoxymethyl glycolic acid 2,6-diethylanilide is prepared,

KpQ 01 136 to 141 ° C, n25 = 1,5176 N-isopropoxymethylglycolic acid 2,6-diethylanilide Kp0, oi 125 to 134 ° 0, nD5 = 1,5146 N-butoxymethylglycolic acid-2.6-diethylanilide

Kp0.01 147 tn 154 ° G 'nD 1,5112 142810 ff-Ethoxyethyl-2,6-diethyl-O-methylsulfonyl-glycolic acid anilide 1b

Example 5

To a solution of 26.5 parts of N-ethoxymethyl-glyeolic acid-2,6-diethylanilide and 13.2 parts of triethylamine in 100 parts of dichloromethane was added at 0 to 5 ° C a solution of 13.8 parts of methanesulfonyl chloride in 20 parts of dichloromethane. . The reaction mixture was kept under stirring at room temperature for 2 hours. For work up, the mixture was washed with ice-cold water and sodium bicarbonate solution. to organic solution was dried over magnesium sulfate and then evaporated in vacuo, to syrupy residue (n + = 1.5170), dissolved in ether / petroleum ether mixture and, after cooling, crystallized with solid CO 2 / acetone, m.p. 43 to 45 ° C.

The compound has the following structural formula: Λη5

/ - <CE -0C H

ΐ

\ - / C-CH -O-S-OH

For example, the dispensing takes place in the form of directly extrudable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, powders, spreading agents, granules, by spraying, misting, spraying, spraying or pouring. the forms of hispensation are entirely directed to the uses; they must in each case ensure as fine a distribution as possible of the active substances according to the invention.

For the preparation of directly sprayable solutions, emulsions, pastes and oil dispersions, medium to high-boiling mineral oil fractions such as kerosene or diesel oil, in addition coal oils, and vegetable or vegetable oils, aliphatic, cyclic and aromatic hydrocarbons, aliphatic, cyclic and aromatic hydrocarbons, for example benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, for example methanol, ethanol, propanol, butanol, chloroform, tetrachlorocarbon, cyclohexanol, cyclohexanone, chlorobenzene and isophorone, highly polar solvents, for example dimethylformamide, for example dimethylformamide , N-methylpyrrolidone and water considered.

Aqueous dispensing forms can be prepared from emulsion concentrates, pastes or wettable powders (spray powders), oil dispersions by the addition of water. For the preparation of emulsions, pastes or oil dispersions, the substances as such or dissolved in an oil or solvent can be homogenized in water by wetting, adhesive, dispersing or emulsifying agents. But concentrates may also be made up of active substance, wetting, adhesive, dispersing or emulsifying agent and optionally solvent or oil which are suitable for dilution with water.

Examples of surfactants are: alkali, alkaline earth, ammonium salts of lignin sulfonic acid, naphthalene sulfonic acids, phenolic sulfonic acids, alkylarylsulfonates, alkyl sulfates, alkyl sulfonates, alkali and alkaline earth salts of dibutylnaphthalene sulfate acid, lauryl ether sulfate acid, lauryl ether sulfate acid, lauryl ether sulfate acid, lauryl ether sulfate acid of sulfated hexadecanols, heptadecanols, octadecanols, salts of sulfated fatty alcohol glycol ether, condensation products of sulphonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or ethylene-ethylphenol, oxyphenolethylene , tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitester, lignin, sulfite waste liquor and methyl cellulose.

142810 18

Powders, scatters or powders can be prepared by mixing or co-grinding the active substances with a solid carrier.

Granules, for example wrapping, impregnation and homogeneous granules, can be prepared by bonding the active substances to solid carriers. Suitable carriers are, for example, mineral soils, such as silica gel, silicic acid, silica gels, silicates, talc, kaolin, aggregates, limestone, lime, chalk, talc, bolus, loose, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, painted formulations, fertilizers such as, for example, ammonium sulphate, ammonium phosphate, ammonium nitrate, urea and vegetable products such as cereal, wood bark, wood and nut shell flour, cellulose powder and other solid carriers. The agents contain between 0.1 and 95% by weight of active substance, preferably between 0.5 and 90% by weight.

To the mixture or individual active substances can be added oils of different types, herbicides, fungicides, nematode diets, insecticides, bactericides, trace elements, fertilizers, anti-foaming agents (for example silicones), growth regulators, antidotes or other herbicidal active compounds, possibly also first immediately before dispensing (tank mix). The last listed herbicidal compounds may also be used before or after the individual active substances of the invention or mixtures thereof.

The mixing of these agents can be made in a weight ratio of 1:10 to 10: 1. The amount used depends mainly on the nature of the desired effect.

The amount used is generally between 0.1 and 15 or more, preferably between 0.2 and 6 kg of active substance per day. ha.

Example 6 In a greenhouse, clay-containing sandy soil was filled in experimental containers and sown with various seeds.

19 U2810

Immediately thereafter, treatment with N-ethoxymethyl-2,6-diethyl-O-methylsulfonyl-glycolic acid anilide (i), III N-methoxymethyl-2,6-diethyl-O-methylsulfonyl-glycolic acid anilide V N-methoxymethyl-2,6- diethyl-O-isopropylsulfonyl-glycolic acid anilide VI N-propoxymethyl-2,6-diethyl-O-methylsulfonyl-glycolic acid anilide VII N-isopropoxymethyl-2, β-diethyl-O-methylsulfonyl-glycolic acid anilide VIII N-methoxymethyl-2.6 dimethyl-O-methylsulfonyl-glycolic anilide IX N-ethoxymethyl-2,6-dimethyl-0-methylsulfonyl-glycolic acid anilide X N-propoxymethyl-2,6-dimethyl-0-methylsulfonyl-glycolic anilide XI N-isopropoxymethyl-2,6 dimethyl-O-methylsulfonyl-glycolic anilide XII N-methoxymethyl-2-methyl-6-ethyl-O-methyl-sulfonyl-glycolic anilide XIV N-ethoxymethyl-O-methylsulfonyl-glycolic acid-2-methyl-6-ethylanilide XV N -methoxymethyl-O-ethylsulfonyl-glycolic acid-2,6-diethylanilide XVI N-propoxymethyl-O-methylsulfonyl-glycolic acid-2-methyl-6-ethylanilide XVII N-isopropoxymethyl-O-methylsulfonyl-glycolic acid-2-methyl-6-eth ylanilide XVIII N-isobutoxymethyl-O-methylsulfonyl-glycolic acid-2-methyl-6-ethylanilide and with N-isopropyl-α-chloroacetanilide (II) and N-methoxymethyl-2-chloroacet-2,6-diethylanilide (XIII) as active comparators.

The amount used in each case was 5 kg of active substance per day.

ha and was in each case dispersed or emulsified in 500 liters of water per hectare. ha.

20 142810

After 3 to 4 weeks, it was found that the active substances I, III, V to XII and XIV to XVIII exhibited a better herbicide effect than the known substances II and XIII at the same compatibility with the culture plants.

The test result is shown in the following table: 21 142810

Active substance I II III V VI

kg of active substance / ha 333 33

Utility Plants;

Brassica napus 00 0 0 0

Zea mays 0 0 0 0 0

Sorghum bicolor 00 0 o 0

Glycine max 0 0 0 5 O

Gossypium hirsutum 0 0 0 0 0

Beta vulgaris - - 10 0 O.

Unwanted plants:

Lolium multiflorum 100 90 95 95 90

Poa annua 100 80 90 100 85

Echinochloa crus-galli 100 75 90 90 80

Digitaria sanguinalis 100 70 80 90 75

Setaria faberii 100 80 90 95 90

Poa trivialis 100 75 85 90 80 0 = without damage 100 = total damage

Active substance VII VIII IX X XI XII xiii kg active substance / ha 3 5 3333 3

Utility Plants:

Brassica napus 0 0 0 0 0 0 40

Zea mays 0 0 0 0 0 0 5 5

Sorghum bicolor 0 0 000 0 20

Glycine max 0 0 000 0 7

Gossypium hirsutum 0 0 0 0 0 0 10

Beta vulgaris 0 0 0 0 0 60 Unwanted plants:

Lolium multiflorum 90 90 95 95 100 90 90

Poa annua 82 100 95 100 100 95 90

Echinochloa crus-galli 80 100 100 100 100 100 95

Digitaria sanguinalis 76 80 90 90 90 85 95

Setaria faberii 85 90 100 100 100 100 95

Poa trivialis 80 90 90 90 92 90 95 22 142810

Active substance XIV XV XVI XVII XVIII

kg of active substance / ha 3 3 3 33

Utility Plants:

Brassica napus 00000

Zea mays 0 0 0 0 0

Sorghum bicolor 00000

Glycine max 0 0 0 0 0

Gossypium hirsutum 00000

Beta vulgaris 00000 Unwanted plants: lolium multiflorum 90 95 95 100 100

Poa annua 90 95 100 95 100

Echinoehloa crus-galli 100 100 100 100 100

Digitaria sanguinalis 100 100 95 95 100

Setaria faberii 95 100 95 95 100

Poa trivialis 95 95 95 95 100 0 = without damage 100 = total damage

Example 7 In a greenhouse, various plants were treated at a height of between 2 and 18 cm with N-ethoxymethyl-2,6-diethyl-O-methylsulfonyl-glycolic acid anilide I, III N-methoxymethyl-2,6-diethyl-O-methylsulfonyl. glycolic acid anilide V N-methoxymethyl-2,6-diethyl-O-isopropylsulfonyl-glycolic acid anilide VI N-propoxymethyl-2,6-diethyl-O-methylsulfonyl-glycolic acid anilide VII N-isopropoxymethyl-2,6-diethyl-O-methylsulfonyl VIII N-Methoxymethyl-2,6-dimethyl-O-methylsulfonyl-glycolic anilide 23. N-ethoxymethyl-2,6-dimethyl-O-methylsulfonyl-glycolic acid anilide X N-propoxymethyl-2,6-dimethyl-O-methylsulfonyl-glycolic acid anilide XI N-isopropoxynethyl-2,6-dimethyl-0-methylsulfonyl glycolic acid anilide XII N-methoxymethyl-2-methyl-6-ethyl-OT-methylsulfonyl-glycolic acid anilide XIV N-ethoxymethyl-0-methylsulfonyl-glycolic acid-2-methyl-6-ethylanilide XV N-methoxymethyl-O-ethylsulfonyl glycolic acid 2,6-diethyl anilide XVI N-propoxymethyl-0-methylsulfonyl-glycolic acid 2-methyl-6-ethylanilide XVII N-isopropoxymethyl-0-methylsulfonyl-glycolic acid 2'-methyl-6-ethylanilide XVIII N-isobutoxymethyl -O-methylsulfonyl-glycolic acid-2-methyl-6-ethylanilide and with N-isopropyl-α-chloroacetanilide (II) and N-methoxymethyl-2-chloroacet-2,6-diethylanilide (XIII) as comparative active substances. The amount used in each case was 3 kg of active substance per day. ha and in each case it was dispersed or emulsified in 500 liters of water per hectare. ha.

After 3 ten? Over the course of four weeks, it was found that the active substances I, III, V to XII and XIV to XVIII are better compatible with the Glycine max. and Gossypium hirsuum showed a better herbicidal effect than the known substances II and XIII.

The test result is shown in the following fable: 142810 24

Active substance I II III V TI VII

kg of active substance / ha_3_3_3_3 3 3

Utility Plants:

Brassica napus 0 0 0 0 0 0

Zea mays 0 0 0 0 0 0

Sorghum bicolor 0 0 0000

Glycine max „0 20 0 0 0 0

Gos sy plum hirsutum 0 20 0 0 0 0

Beta vulgaris - - - 0 5 - Unwanted plants:

Lolium multiflorum 100 40 80 70 80 70

Boa annua 100 25 95 64 80 70

Echinochloa crus-galli 60 30 60 60 65 70

Digitaria sanguinalis 65 50 60 60 60 65

Setaria faberii 60 30 65 64 65 65

Poa trivialis 100 60 90 70 75 75

Active substance VIII IX X XI XII XIII

kg of active substance / ha 3 33333

Useful plants%

Brassica napus 10 - 0 - 0 30

Zea mays 0 0 0 0 0 5

Sorghum bicolor 0 0 0 0 0 15

Glycine max »0 0 0 0 0 5

Gossypium hirsutum. 0 0 0 0 0 5

Beta vulgaris 0 5 0 5 0 20 Unwanted plants:

Lolium multiflorum 80 70 75 80 70 45

Poa annua 90 65 70 90 65 50

Echinochloa crus-galli 70 60 70 75 65 40

Digitaria sanguinalis 65 60 65 70 60 40

Setaria faberii 70 60 70 75 67 45

Poa trivialis 80 70 70 75 70 40 0 = without damage 100 = total damage „c 142810 25

Active substance XIV XV XVI XVII XVIII

kg of active substance / ha 535 3 3

Utility Plants:

Brassica napus 000 0 0

Zea mays 0 0 0 0 0

Sorghum bicolor 000 0 0

Glycine max. 000 0 0

Beta vulgaris 000 0 0 Unwanted plants:

Lolium multiflorum 85 70 80 70 90

Poa annua 90 75 80 70 90

Echinochloa crus-galli 80 70 75 75 85

Digitaria sanguinalis 75 75 85 75 85

Setaria faberii 75 75 80 70 85

Poa trivialis 85 80 75 80 90 0 = without damage 100 = total damage

Example 8

90 parts by weight of Compound I are mixed with 10 parts by weight of N-methyl-α-pyrrolidone and a solution suitable for use in very small droplets is obtained.

Example 9 20 parts by weight of compound I are dissolved in a mixture consisting of 80 parts by weight of xylene, 10 parts by weight of the preparation product of 8 to 10 moles of ethylene oxide to 1 mole of oleic acid N-monoethanolamide, 5 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the product of 40 mole of ethylene oxide to 1 mole of castor oil. By pouring and finely distributing the solution in 100,000 parts by weight of water, an aqueous dispersion containing 0.02% by weight of the active substance is obtained.

26 1A 2810

Example 10 20 parts by weight of the compound I are dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the preparation product of 7 moles of ethylene oxide to 1 mole of isooctyl-pbenol and 10 parts by weight of. the preparation product of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring and finely distributing the solution in 100,000 parts by weight of water, an aqueous dispersion containing 0.02% by weight of the active substance is obtained.

Example 11 20 parts by weight of Compound I are 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 210 to 280 ° and 10 parts by weight of the preparation product of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring and finely distributing the solution in 100,000 parts by weight of water, an aqueous dispersion containing 0.02% by weight of the active substance is obtained.

Example 12 20 parts by weight of the active substance I are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalene-a-sulfonic acid, 27 parts by weight of the sodium salt of a lignin sulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel and milled in a hammer mill. A fine distribution of the mixture in 20,000 parts by weight of water results in a spray liquid containing 0.1% by weight of the active substance.

Example 13 3 parts by weight of Compound I are thoroughly mixed with 97 parts by weight of finely divided kaolin. In this way, a powder containing 3% by weight of the active substance is obtained *