DD152904A5 - HERBICIDE MEDIUM - Google Patents

Abstract

Two-component herbicidal agents. The compositions according to the invention contain from 20 to 90% by weight of the compounds of the general formula (I) in which R & ind1! and R & ind2! C & ind1-6! -Alkyl or -cycloalkyl, or together denote a hexamethylene group and the general formula II, wherein R & ind3 !, R & ind4! and R & ind5! are the same or different and are hydrogen or chlorine, and 0 to 70 wt .-% of liquid Verduennungsmitteln and 5 to 10 wt .-% of surface-active agents.

Description

Berlin, January 29, 1981

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Herbicidal agents

Field of application of the invention

The invention relates to two-component herbicidal compositions for use in agriculture.

Characteristic of the known technical solutions

Among the herbicidal agents are the thiolcarbamates of general formula I.

HGS - C ₂ H ₅ (I), ^R 2 O

wherein IL and R ₂ C-, - alkyl or cycloalkyl or together represent a hexamethylene group. ¹ and their combinations with other herbicides, eg. B. with triazines and Piridazonderivaten known.

The thiolcarbamates of the general formula I and the agents containing these active compounds are described, for example, in US Pat. Nos. 2,913,327, 3,037,853, 3,175,897, 3,185,720, 3,198,786 and 3,582,314 and in HU-PS 157,558 and 160 635.

The use of thiocarbamates alone has not been practically widespread because they are mainly monocotyledons. Destroy weeds and damage the crops. If these funds are included in the recommended concentration

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be used to destroy the various weeds, takes place to a large extent, the malformation and stunting of crops, As a result of damage to crops reduces the crop yield ·

In practice, the combination of thiolcarbamates with triazines has not spread since resistant weed species are formed against the triazine type herbicidal insecticides and degradation of the triazines in the soil is slow, they accumulate and thus their usefulness is limited «The thiolcarbamates continue to damage crops ·

To control these obstacles, the seeds of the crops were treated with antibodies before planting them (US Pat. Nos. 3,131,509 and 3,564,768). However, these antibodies are not effective enough, so they have not spread ·

Later, antidotes were used because of the damaging effect of the thiolcarbamates used alone or in combination with other agents and / or to increase the resistance of the plants. Thiolcarbamate-type herbicides containing such anti-dopant agents are described in HU-PS 165 736, 168 977 and 170 214. The disadvantage of thiocarbamates containing only antidotes is that they destroy only the monocotyledonous weeds, the destruction of dicotyledonous weeds is uncertain.

The Hexamethylenimidderivate the general formula II

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CH ₀ -CH ₉ -CH 2 2

CH ₂ - OH ₂ -

wherein R-, R, and R ₁ - are the same or different and are hydrogen or chlorine, are not known as herbicides either in themselves or in combinations.

Object of the invention

The aim of the invention is the provision of new agents with improved herbicidal activity, broad spectrum of selectivity and good compatibility with crop plants.

, Loan of the essence of the invention

The object of the invention is to provide two-component herbicidal compositions having the desired properties.

According to the invention, the two-component novel herbicidal compositions contain the compounds of the general formulas I and II

R ₁

R ₂ 0

CS-C ₂ H ₅ (I)

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(II)

R ₁ and Rp C, - alkyl or cycloalkyl or together represent a hexamethylene group and '

R ^, R ₄ and Rj- are identical or different and denote hydrogen or chlorine.

It has now been found that the herbicidal agent which comprises the compounds of the general formulas I and II, in which R.sup.1 and R.sup.p are C, g-alkyl or cycloalkyl or together form a hexamethylene group, and R.sup.1, R.sup.2 and R.sup.2- are the same or different and are hydrogen or chlorine, in a ratio of 1 ": 0.05 to 1: 1, at a rate of 3 to 15 kg / ha both the monocotyledons (Avena fatua, Cynodon dactylon, Digitaria ssp. , Echinocloa ssp., Eleusine ssp., Eragrostis ssp., Lolium ssp., / Multi-florum /, Poa ssp. / Annua /, Setaria ssp., Sorghum holepense), as well as the dicotyledonous weeds (Arnoranthus spp., Chenopodium album , Laminum amplexicoule, Linum Usitatissimum, Polygonum ssp, Planago lanceolata, Portulaca olazacea, Spergula arvensis, Stelloria media, Solonum nigrum, Amboria spp.) And without damaging crops even without the addition of known antidote agents.

¹ · ¹⁹⁸¹

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embodiment

The invention is explained in more detail below with reference to some examples.

To test the biological activity of the herbicidal compositions according to the invention, the hybrid maize (Zea mays / L /) of the types MVFV-26 and MVTC-596 were used as test plants. Among the crop plants, these are the most sensitive to the thiolcarbamate compounds and the herbicidal gowns containing thiolcarbamate compounds are the most widely used in the field.

The biological activity of the agent according to the invention was investigated both in vessels and in petri dishes in the agar-agar bioassay.

The investigations in the vessels were carried out in the following way:

In plastic containers with a surface area of 1.2 dm, 500 g of the bottom, thrown through a 2 mm diameter sieve, were weighed in each case. Thereupon 4 grains of the hybrid maize (Zea mays / L /) of the type MVFV-26 as well as each 0.3 g of the weed seeds of the Polygonum ssp., Setaria ssp. and sown by the Plantago lanceolate. Then 100 g of the soil was placed, then treated with the agent of the invention. After treatment, another 200 g of the soil was weighed into each tube. During the tests the average daily temperature was' 24.3 ⁰ G and the relative daily average humidity 54 »8%, the plants were using artificial sun lamps of 400 W, and cultured using an illumination period of 12 hours. The water loss was replaced daily .. The

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Experiments were evaluated on the 14th day. The results are given in Table 1.

Table 1

treatment Abscess length .cm % Fri s sblat tgewi cht S % untreated control A ₁ B ₁ 40.2 100 38.1 94.7 34.5 85.8 6.8 100 6.8 100 5.9 86.8 SD P = 5 % ± 18.6 + 24.6

A ₁ = 5 »6 kg / ha ^, IT-di-n-propyl-S-ethyl-thiocarbamate + 0.56 kg / ha l-f (dichloro-acetyl) -hexa-ethylene-ethylene-imide

B ₁ = 5 »6 kg / ha H, N ~ di-n-propyl-S'ethyl-thiolcarbamate + 0.56 kg / ha! - (trichloro-acetyl) hexamethylene-imide

After treatment with the active ingredient combination "A ₁ ", the shark is undamaged and healthy, but in the case of treatment with the active ingredient combination "B ₁ " was to a small extent a deformation and winding.

The agar-agar bioassay was carried out in the following manner:

In petri dishes, we weighed in 300 g of an agar-agar solution (0.4% ) and the mixture of the corresponding doses of the combinations "A ₂ " and "B ₂ ". Six grains of hybrid maize (Zea mays / L /) of the MVFV-26 type were sown on the surface of the poured and fixed nutrient medium. The experiments were repeated three times.

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The ratings were on the 7th day. The results are given in Table 2.

Table 2

treatment ρ = 5 % Absperse length cm % 100 Fry weight g % 100 untreated control 10.7 101.9 1.7 102.9 A ₂ 10.9 64.5 1.75 91.2 ^B 2. 6.9 + 30.4 1.55 + 40 SD

= 0.56 kg / ha NjlT-di-n-propyl-S-ethyl-tliolcarbamate + 0.056 kg / ha lT- (dichloro-acetyl) -hexamethylene-imide - 0.56 kg / ha Ν, Ν-di-n -propyl-S-ethyl-thiocarbamate + 0.056 kg / ha U-CTriclilor-acetyD-hexamethylene-imide

Experiments were carried out by examining the biological effect of the active substance combinations containing the active ingredients, ie. H. Η, ϊΓ-di-n-propyl-S-ethyl-thiocarbamate and T-dichloroacetyl-hexamethylene-imide and Ν, ίΓ-hexamethylene-S-ethyl-thiocarbamate and IT- (dichloro-acetyl) -hexamethylene imid in different proportions contained. The experiments were carried out in the following way:

The test plants were grown in plastic containers of weighed meadow soil (total amount 700 g) using artificial altitude suns of 400 Y / and using a lighting period of 12 hours. The water-

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loss was replaced up to 65 % of the total water capacity daily. 4OO g of the air-dry soil, which had been thrown through a 2 mm diameter sieve, was weighed into each vessel. The weed seeds (Schinocloa crus galli, Setaria glauca, Cheno.podium album and Linum usitatissimum) and the crop (LiVTC-596 hybrid corn) were then sown in the soil. On top of that, 200 grams of the soil were placed, followed by spraying on the appropriate amounts of the herbicides. After treatment, 100 g of the soil was weighed into each tube. The evaluation was made on the 12th day, and the abscess length and the cornea weight of the corn as well as the leaf weight of the monocotyledonous and dicotyledonous weeds were measured. The results were checked with the variance analysis. Table 3 contains the herbicidal activity and the effect on the frit leaf weight of Itf ~ (dichloroacetyl) hexamethylene imide in itself, the effect of the combinations are summarized in Tables 4, 5 and 6 and 7. The data were calculated according to SR Colby (Calculating Sinergistic and Antagonistic Responses of Herbicide Combinations, Weed, 15, 1, 20-22 / 1967 /).

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Table 3

Dose of IJ- (di-chloro-acetyl) -hexamethylene-imide Corn FRIS blade weight Dicotyledonous % 100 kg / ha Just a leafy one weeds 100 31 he 44 43 untreated control 100 52 49 0.0049 96.5 47.5 43 0,049 78.5 66 52.5 0.098 95 57 43 0.196 89 74 62 0.392 88.5 74 30 0.784 84 46.5 35 1,568 80.5 - 37 3,136 77 4,900 73.5

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Table 4

Dose of N.EHDi-n-propyl-S- et.hyl-t.hiolcarbamate Dose of I "T- (dichloroacetyl) - hexaraethyleriimide Corn fell off FRIS blade weight kg / ha kg / ha % One-two-leaved, leafless weeds of weeds 0 O 100 / o% 5.6 O 46.3 100 100 5., 6 0.0056 60.8 0 12,1 5.6 0,056 * 65.0 0 15.5 5.6 0.112 62.6 0 11.5. 5.6 0.224 65.9 0 18.4 5.6 0,448 85.5 0 12,1 5.6 0.896 97.9 0 0 5.6 1,792 94.4 0 13.8 5.6 3,584 94.7 0 7.5 5.6 5.6 88.5 0 8.6 0 12.7

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Table 5

Dose of Ν, ΪΤ-di-n-propyl-S-ethyl-thiol Dose of U- (dichloroacetyl) -hexamethy- Dicots - Corny weeds _ ^ Fry leaf weight gefun calculation gefun carbamate len-imide calculation the net the kg / ha kg / ha net % Cf /O % - 0 0 % 100 100 100 5.6 0 100 64 12.1 12.1 5.6 0.112 64 68.7 4.4 18.4 5.6 0.224 51.5 63.2 2.9 12.1 5.6 0,448 54.0 87.4 9.2 0 5.6 0,896 - 54.6 88.2 7.8 13.8 5.6 1,792 58.0 75.7 8.7 7.5 5.6 3,584 55.5 81.2 5.7 8.6 5.6 5.6 51.5 75.7 6.4 12.7 51.5

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Table 6

Dose of N, N-di-n-propyl-S-ethyl-thiol-carbamate kg / ha Dose of N- (dichloroacetyl) -hexamethylene-imide kg / ha Corn Seed length % Prissblattg Einkeim leafy weeds % weight of dicotyledonous weeds 3 »0 0 100 100 100 4.9 0 89 _? 0 5.8 39.3 4.9 0.0049 88.6 0 26.7 4.9 0,049 93.6 0 28.9 4.9 0.098 96.0 0 36.2 4.9 0.196 99.1 7.7 18.5 4.9 0.392 95.3 9.6 6.7 4.9 0.784 90.0 0 23.8 4.9 1,568 92.5 0 28.9 4.9 3,136 92.5 0 16.2 4.9 4.9 87.7 7.7 18.4

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Table 7

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Dose of H, N-di-n-propyl-S-ethyl-thiol-carbamate Dose of EKDichloroacetyl) - hexamethylene imide τ ,. , Zv / ^Max's eikeimblätt- engined weeds Friš blade weight found be calculated found kg / ha kg / hg without t % % % 0 0 % 100 100 100 • 4.9 0 100 82.0 30.0 39.3 4.9 0.098 82.0 89.8 19.5 36.2 4.9 0.196 78.1 94.5 18.5 16.8 4.9 0.392 73.0 86.7 20.7 9.6 4.9 0.784 73.0 78.9 17.2 23.8 4.9 1,568 69.1 82.0 24.4 28.9 4.9 3,136 65.9 83.5 11.6 16.2 4.9 4.9 62.7 80.4 14.0 18.4 60.2

It can be seen from the data in the tables that the compositions according to the invention destroy both monocotyledonous and dicotyledonous weeds to a good degree and do not damage the cultivated plants. The compounds of the general formula II in which R ~, R> and Rj- are the same or different and represent hydrogen or chlorine can be prepared without any restriction in the following examples.

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example 1

19.6 g (0.25 mol) of acetyl chloride are mixed with 50 ml of acetone, then filled into a equipped with a thermometer, stirrer and dropping funnel flask. The reaction mixture is cooled with a mixture of common salt / ice. The dropping funnel is then filled with the mixture of 50.58 g (0.51 mol) of hexamethylenimine and 50 ml of acetone, then this mixture is heated at a temperature of 5 to 10 ⁰ C., with stirring, added to the mixture of acetyl chloride and acetone. After completion of the addition, the reaction mixture is stirred for a further hour at room temperature. Thereafter, for about 20 minutes, dry hydrochloric acid gas is passed through the reaction mixture. If the reaction mixture does not contain free hexamethyleneimine after determination by thin layer chromatography, the hexamethyleneimine hydrochloride is filtered from the reaction mixture, then the acetone is removed from the filtrate in vacuo.

The obtained Itf-acetyl-hexamethylene-imide is light yellow, crystalline material with a melting point of 85 to 87 ⁰ C.

Yield: 33.48 g, 95 % of theory. Analysis: calculated H % 9.92 found H % 9.98

Example 2

28.23 g (0.25 mol) of acetyl chloride is dissolved at room temperature in 50 ml of acetone, then filled into a equipped with a thermometer, stirrer and dropping funnel flask. The reaction mixture is cooled with the mixture of saline / ice. The mixture of 50.58 g (0.51 mol) of hexamethyleneimine and 50 ml of acetone is then charged to the dropping funnel,

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Thereafter, this mixture is added at a temperature of 5 to 10 ⁰ C with stirring, your mixture of acetyl chloride and acetone. After completion of the addition, the reaction mixture is stirred for a further hour at a temperature of 10 to 15 ⁰ C. The reaction mixture thus obtained is then poured with stirring into ice water of about three times the amount, then the organic and the aqueous phase is separated. The aqueous phase is washed with the same amount of 0.1 U hydrochloric acid solution and separated after elimination. The organic phase is washed again with water until the wash water is neutral and then dried over sodium sulfate. The acetone is then in the aqueous phase.

The resulting IT (chloroacetyl) hexamethyleneimide is a light yellow liquid with a refractive index of njp = 1.5064; nj ° = 1.4889.

Yield: 41.68 g, 95 % of theory

Analysis: calculated N % 7.97 Cl % 20.22 found Έ% 7.92 Cl% 20.46

Example 3

37 g (0.25 mol) of dichloro-acetyl chloride is dissolved at room temperature in 50 ml of acetone, then filled into a equipped with a thermometer, stirrer and dropping funnel flask. The reaction mixture is washed with a mixture of. Brine / ice cooled · In the dropping funnel, the mixture of 50.58 g (0.51 mol) of hexamethylene-imine and 50 ml of acetone is then filled, then this mixture at a temperature of 5 to 10 ⁰ C while stirring the mixture of dichloroacetyl chloride and acetone were added. After the completion

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the addition of the reaction mixture is stirred for one hour at a temperature of 10 to 15 C. The reaction mixture thus obtained is then poured with stirring into ice-water approximately three times the amount, after which the precipitated product filtered off with suction, and water with 0.1 H ^- suspended hydrochloric acid solution. After excretion, the hydrochloric acid phase is filtered off with suction, then washed with water until the washings are neutral and then dried.

The resulting dichloroacetyl-hexamethylene-imide attaches heavily and is a light yellow, powdery material with a melting point of 52 to 54 C and a bromide.

70

index of n-A = 1.5040.

Yield: 48.3 g, 92 % of theory

Analysis: calculated Έ% 6.66 Cl% 33.80 found Ii % 6.51 Cl % 33.85

Example 4

45 »5 g (0.25 mol) of trichloro-acetyl chloride are dissolved at room temperature in 50 ml of acetone, then filled into a flask equipped with thermometer, stirrer and dropping funnel. The reaction mixture is cooled with a mixture of common salt / bis. The mixture of 50.58 g (0.51 mol) of hexamethylene-imine and 50 ml of acetone is then added to the dropping funnel, after which this mixture is stirred at a temperature of 5 to 10 ^° C. with stirring to the mixture of trichloroacetyl chloride and Acetone added. After completion of the addition, the reaction mixture is stirred for a further hour at a temperature of 15 to 20 ⁰ C. The reaction mixture thus obtained is then poured with stirring into ice water of about three times the amount, then the organic and aqueous phase separated. The organic phase

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is washed with the same amount of a 0.1 N hydrochloric acid solution and separated after elimination. The organic phase is washed again with water until the wash water is neutral, then dried over ITatrium sulfate and filtered. The acetone is in the aqueous phase.

The obtained IT- (trichloro-acetyl) -hexamet.-ethylene-iiaide is a brownish red liquid .. with a refractive index of np ° = 1.5253; nj ° = 1.5060.

Yield: 57.45 g, 94 5 o the theory Cl % 43 , 55 Analysis: calculated H " % 5.72 Cl % 42 97 N % 5.36

_s The erfi'ndungsgemäßen, two components containing herbicidal compositions comprise the compounds of the general formulas I and II in 20 to 90%. In the general formulas I and II, R ^ and R ₂ are C, g-alkyl or cycloalkyl, or together form a Hexaniethylengruppe, R ^, R * and R ₁ - are) the same or different and are hydrogen or chlorine. The compositions according to the invention are formulated in the form of emulsifiable concentrates, since the compounds of general formula I are liquid.

During the formulation, 19.8 to 89 parts by weight of the compound of the general formula (I) are weighed in, then from 0 to 70 parts by weight of a diluent, then with stirring from 0.2 to 45 parts by weight of a compound of general formula II. Preferred diluents are kerosene, aliphatic and aromatic chlorinated hydrocarbons, aromatic hydrocarbons, dimethylformamide and dimethylsulphoxide. The resulting mixture is

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The surface-active agents are preferably the mixtures of anionic and nonionic surfactants, for example the mixture of dodecyl-benzenesulfonic acid calcium salt and of polyoxy-alkyl-phenols or the like Mixture of alkylaryl sulphonic acid salt and of alkyl phenol polyglycol ether in embossing Palis the mixture which still contains suspended impurities after homogenization, it is filtered The formulation is illustrated without any limitation with the following examples:

Example ^ J? ,

Into a flask equipped with a shermometer and stirrer are weighed 102 g of HjN-di-n-propyl-S-ethyl-thiocarbamate having an active ingredient content of 98 % and 68 g of kerosene, followed by stirring with 10 g of H- (dichloroacetyl) hexamethyleneimide The reaction mixture is stirred for 30 minutes at room temperature, then 8 g of Atlos 3400 B and 12 g of Atlox 4857 B are added as emulsifier. The reaction mixture is stirred for 30 minutes, then filtered.

200 g of emulsifiable concentrate are obtained, the total active substance content of which is 110 g.

Atlox 3400 B and Atlox 4857 B consist of a mixture of dodecylbenzenesulfonic acid calcium salt and polyoxyethylene-alkyl-phenols ·

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• - 19 Example 6

Into a flask equipped with thermometer and stirrer are weighed 163 g of IT-di-n-propyl-S-ethyl-thiocarbamate having an active ingredient content of 98 % and 20 g of N- (dichloro-acetyl) -hexamethylene-imide, then the reaction mixture stirred for 30 minutes at a temperature of 35 to 40 ⁰ C · to the reaction mixture is then added 20 g Emuisogen 1-40 as an emulsifying agent, and stirring continued for 30 minutes, then filtered.

This gives 200 g of emulsifiable concentrate whose total active substance content is 180 g.

Emulsifier Emuisogen I-40 consists of the mixture of alkyl-aryl-sulfonic acid-calcium salt and of alkyl-phenylpolyglycol-ether.

Example 7

In a flask equipped with a thermometer and stirrer, I46 g of ΙΤ, Ιί-di-n-propyl-S-ethyl-thiocarbamate with an active substance content of 98 % and 20 g of kerosene were weighed, then 16 g. With stirring; - (dichloro-acetyl hexamethyleneimide was added and the reaction mixture was stirred for 30 minutes at a temperature of from 35 to 40 ° C. 8 g of Tensiofix® IS and 12 g of Tensiofix® AS as emulsifying agent were then added to the reaction mixture thus obtained, then at a temperature of from 35 to 30 minutes Stirred 40 ⁰ C, then filtered.

200 g of emulsifiable concentrate are obtained, the total active substance content of which is 159 g.

Emulsifiers Tensiofix IS and Tensiofix AS consist of a mixture of anionic and nonionic surfactants,

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Example 8

The emulsifiable concentrate is prepared analogously to Example 7, but instead of 20 g of kerosene, 20 g of dichloroethane are used.

Example 9

The emulsifiable concentrate is prepared analogously to Example 7, but 20 g of dimethylformamide are used instead of 20 g of kerosene.

BeJSpJeI ₁ 10

The emulsifiable concentrate is prepared analogously to Example 7, but 20 g of xylene are used instead of 20 g of kerosene.

Example 11

The emulsifiable concentrate is prepared analogously to Example 7, but instead of 20 g of kerosene, 20 g of chlorobenzene are used.

Example 12

The emulsifiable concentrate is prepared analogously to Example 7, but instead of 20 g of kerosene, 20 g of dimethyl sulfoxide are used.

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Example 13

Into a flask equipped with a thermometer and stirrer are weighed 73 g of NjlT-di-n-propyl-S-ethyl-thiocarbamate having an active ingredient content of 98 % and 14 g of kerosene, followed by stirring 8 g of lT- (dichloroacetyl) hexamethylene imide and the reaction mixture was stirred for 30 minutes at a temperature of 35 to 40 ⁰ C. The reaction mixture is then added 6 g Emuisogen 1-40 as an emulsifying agent, followed by stirring for 25 minutes at a temperature of 35 to 40 ⁰ G, then filtered.

This gives 100 g of emulsifiable concentrate whose total active substance content is 80 g.

Example 14

146 g of ITjN-di-n-propyl-S-ethyl-thiocarbamate with an active substance content of 98 % and 28 g of kerosene are weighed into a flask equipped with a thermometer and stirrer, then 14.6 g of li- (trichloro-acetyl) with stirring. hexamethyleneimide was added and the resulting reaction mixture stirred for 15 minutes at a temperature of 35 to 40 ⁰ C. To this reaction mixture is added 12 g of Emuisogen 1-40 as emulsifier, then stirred for 25 minutes at a temperature of 35 to 40 C, then filtered.

200 g of emulsifiable concentrate are obtained, the total active substance content of which is 158 g.

Example 15

In a equipped with a thermometer and stirrer 'piston 146 g lT, H-di-n-propyl-S-ethyl-thiolcarbamat with

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weighed an active ingredient content of 98% and 20 g of xylene, then 14.6 g of N- (chloro-acetyl) -hexamethylenimid added with stirring and the reaction mixture for 30 minutes at a temperature of 35 to 40 ⁰ C stirred. The reaction mixture thus obtained 8 g of Atlox 3400 B and 12 g of Atlox 4857 B was added as the emulsifying agent, followed by stirring at a temperature of 35 to 40 ⁰ C for 30 minutes, then filtered ·

This gives 200 g of emulsifiable concentrate whose total active ingredient content is 158 g.

Example 16

146 g of IT, IT-di-n-propyl-S-ethyl-thiocarbamate having an active substance content of 98 % and 20 g of xylene are weighed into a flask equipped with thermometer and stirrer, then 14-6 g of IJ-acetyl-hexamethylene are added with stirring The reaction mixture is then stirred for 40 minutes at a temperature of 35 to 40 ° C. To the reaction mixture are then added 8 g of Atlox 3400 B and 12 g of Atlox 4857 B as emulsifier, followed by 30 minutes at a temperature of 35 to 40 ° 0 stirred, then filtered.

200 g of emulsifiable concentrate are obtained, the total active substance content of which is 158 g.

At game 17

In a flask equipped with a thermometer and stirrer, 150 g of lI, U ~ hexamethylene-S-ethyl-thiolcarbamate and 18.5 g of kerosene are weighed, then 12 g of R- (dichloro-acetyl) -hexamethylene-imide are added with stirring and the reaction mixture 15 minutes at a temperature of 25 to

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30 C stirred. Then 4 g of Atlox 3400 B and 16 g of Atlox 4857. B are added to the reaction mixture as emulsifier, then stirred for 15 minutes at a temperature of 25 to 30 ⁰ C, then filtered. , '

This gives 200 g of emulsifiable concentrate, the total active substance content is 162 g.

Example. 18

Into a flask equipped with a thermometer and stirrer, 150 g of IT, hexamethylene-S-ethyl-thiocarbamate and 28.5 g of xylene are weighed, then 92 g of di- (dichloroacetyl) -hexamethylene-imide are added with stirring and the reaction mixture 30 Stirred for minutes at a temperature of 35 to 40 g. To the reaction mixture, 6 g of Atlox 3400 B and 24 g of Atlox 4857 B are then added as an emulsifying agent, followed by stirring at a temperature of 35 to 40 ⁰ C for 15 minutes, then filtered.

This gives 300 g of emulsifiable concentrate whose total active substance content is 242 g.

Example 19

In a equipped with thermometer and stirrer flask 36.7 g of Ν, Ν-di-n-propyl-S-ethyl-tliiolcarbamat and 140 g of kerosene are weighed, then with stirring 4 g !! - (Dichlororr acetyl) hexamethylene iraid added and the reaction mixture stirred at a temperature of 20 to 25 ⁰ C at full solution, then filtered.

This gives 200 g of emulsifiable concentrate whose total active substance content is 40.7 g.

Claims (2)

Invention sanction 1, two-component herbicidal compositions, characterized in that it contains 20 to 90 wt _o -% of the compounds of the general formula (i) C ₂ H ₅ (D wherein
R. and and (II) C, g-alkyl or cycloalkyl, or together represent a hexamethylene group CH, CH, CH, • GH CH, CH ti ι OR ₁ . R  R (II) wherein R ~, R and R _{5 are the} same or different and denote hydrogen or chlorine _? and 0 to 70% by weight of liquid diluents and 5 to 10% by weight of surfactants. 2. Herbicides according to point 1 _? characterized in that they contain the compounds of the general formulas (I) and (II) in a ratio of 1: 0.05 to 1: 1,