CS196241B2 - Herbicide - Google Patents

Description

CZECHOSLOVAK SOCIALIST REPUBLIC (19) DESCRIPTION OF THE INVENTION PATENT (22) Registered 13 04 72 (21) (PV 2480-72) (32) (31) (33) Priority from 16 04 71 (134868) and from 09 12 71 (208041) United States of America (40) Published 29 08 79 OFFICE AND DISCOVERY OFFICE (45) Published 15 12 82 196241 (11) (B2) (51) Int. Cl, 3A 01 N 37/18 (72) (73)

The author of the invention PALLOS FERENG MARCUS, WALNUT CREEK, and at the same time. BROKKE MERVIN EDWARD, MORAGA and ARNEKLEV DUANE RANDALL, SUNNYVALE (Sp. St.) Patent holder (54) Herbicide 1

Among the many commercial herbicidal compounds, thiolcarbamates, either alone or in admixture with other herbicides, such as triazines, have achieved relatively high commercial success. These herbicides have an immediate toxic effect on a large number of weeds, at different concentrations, depending on the weed resistance. Examples of some of these compounds are described in U.S. Patent Nos. 2,913,337.3,037,853, 3,175,897, 3,185,720, 3,198,786 and 3,582,314. In practice, it has been found that the use of thiolcarbamates as herbicides in useful plants has sometimes been leads to severe damage to the crop. When applied in the recommended amounts, to the broadleaf and grass weeds, severe deformations and stunted growth of useful plants occur. This abnormal crop growth has resulted in a reduction in crop yields. Previous attempts to overcome this problem consisted in treating the seeds of the crop plants before sowing or planting with certain antagonists (see U.S. Pat. No. 3,131,509). However, the use of said antagonist agents has not been significant.

It has now been found that plants can be boiled before being damaged by thiolcarbamates, whether 198341 2 alone or in admixture with other compounds, and / or to substantially increase tolerancirostlin against the active ingredients described above in the U.S. patent application. applies an antidote compound (hereinafter referred to as an antidote). SUMMARY OF THE INVENTION The present invention relates to an S-ethyl-dipropylthiocarbamate herbicide, S-ethyl-diisobutylthiolcarbamate, S-propyl dipropylthiolcarbamate, S-2,3,3-trichlorallyl-diisopropylthiolcarbamate, S-ethyl-cyclohexylethylthiocarbamate, 2 -chloro-2 ', 6'-diethyl-N- (methoxymethyl-acetanilide, S-ethyl-hexahydro-1H-azepine-1-cariioate, 2-chloro-N-isopropylacetanilide, N, N-diallyl-2- chloroacetamide, S-4-chlorobenzyldiethylthiolcarbamate, 3-2-chloro-4-ethylamino-6-β-pentafluoro-n-s-triazine, 2-chloro-4,6-bis (ethylamino) -s-triazine, 2 - (4-chloro-6-ethylamino-s-triazin-2-ylamino) -2-methyl-propionitrile, 2-chloro-4-cyclopropylamino-6-isopropylamino-s-trlazine,

2,4-D or mixtures thereof, characterized in that it contains as the antidote compound a compound of formula (IO). II / R — C — N (I), \ t

Wherein R is a halogenalkyl group having from 1 to 20 carbon atoms, a haloalkenyl group having from 2 to 20, preferably from 2 to 12, an carbon atom, an alkyl group having from 1 to 20 carbon atoms, carbonyl, alkenyl having 2 to 20, preferably 2 to 12 atoms. carbon, a cycloalkyl group having not more than 20 carbon atoms, a cycloalkyl group in which the cycloalkyl group has in each case not more than 20 carbon atoms, a halogen atom, a hydrogen atom, an alkoxycarbonyl group in which the alkoxy moiety contains 1 to 20 carbon atoms, the N-alkenylcarbamoylalkyl group in which the alkenyl moiety contains 2 to 20, preferably 2 to 12 carbon atoms, and the alkyl moiety is 1 to 20 carbon atoms, the N-alkenylcarbamoyl moiety in which the alkenyl moiety is is 2 to 20, preferably 2 to 12, carbon atoms, the N-alkyl-N-alkenylcarbamoyl group in which the alkyl moiety contains 1 to 20 carbon atoms and the alkynyl moiety is 2 to 20, preferably 2 to 12 carbon atoms, N- an alkyl-N-alkynylcarbamoyl group in which each of the alkyl moieties each contains 1 to 20 carbon atoms and the alkynyl moiety contains 2 to 20, preferably 2 to 12 carbon atoms, an N-alkenylcarbamoyl alkoxyalkyl group , in which the alkenyl moiety contains 2 to 20, preferably 2 to 12 carbon atoms, and the alkoxy and alkyl moieties each contain 1 to 20 carbon atoms, the N-alkyl-N-alkynylcarbamoylalkoxyalkyl group in which each alkyl and alkoxy moiety each has 1 to 20 carbon atoms and alkynyl the moiety contains 2 to 20, preferably 2 to 12 carbon atoms, alkynyloxy having 2 to 20, preferably 2 to 12 carbon atoms, haloalkoxy having 1 to 20 carbon atoms, thiocyanatoalkyl having 1 to 20 carbon atoms in the alkyl moiety, an alkenylaminoalkyl group in which the alkenyl moiety contains 2 to 20, preferably 2 to 12, carbon atoms and the alkyl moiety contains 1 to 20 carbon atoms, an alkylcarbonylalkyl group in which each alkyl moiety contains 196,241,411 to 20 carbon atoms each , a cyanoalkylene group having 1 to. Carbon atoms in the alkyl moiety, cyanoalkyl moieties having from 1 to 20 carbon atoms in the alkyl moiety, alkenylanthalosulphonalkyl moieties in which the alkenyl moiety contains from 2 to 20, preferably from 2 to 12 carbon atoms, and the alkyl moiety contains from 1 to 20 carbon atoms, alkylthioalkyl a group in which each of the alkyl moieties each contains 1 to 20 carbon atoms, a haloalkylcarbonyl-oxyalkyl moiety in which each of the alkyl moieties each contains 1 to 2: 0 carbon atoms, an alkoxycarbonylalkyl group in which both the alkoxy and alkyl moieties each contain From 1 to 20 carbon atoms, a haloalkenyl-carbonyloxyalkyl group in which the alkenyl moiety contains 2 to 20, preferably 2 to 12, carbon atoms and the alkyl moiety contains 1 to 20 carbon atoms, hydroxyhaloalkoxyalkyl in which both alkoxy -a so. the alkyl moiety in each case has 1 to 20 carbon atoms, a hydroxyalkylcarbonylalkoxy-alkyl group in which each of the alkyl moieties contains 1 to 20 carbon atoms and the alkoxy moiety contains 1 to 20 carbon atoms and the alkoxy moiety contains 1 to 20 carbon atoms, hydroxyalkyl moiety with 1 up to 20 carbon atoms, an alkoxysulfonoalkyl group in which both alkoxy and alkyl groups each contain 1 to 20 carbon atoms, a furyl group, a thienyl group, an alkyldi-thiolenyl group in which the alkyl moiety contains 1 to 20 carbon atoms, a thlenylalkyl group with 1 to 20 carbon atoms in the alkyl moiety, a phenyl group, a substituted phenyl moiety wherein the substituents are selected from the group consisting of halogens, alkyl groups having 1 to 20 carbon atoms, haloalkyl groups having 1 to 20 carbon atoms, 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, carbamoyl groups, nitro groups, carboxylic acid radicals and their salts and logenalkylcarbamoyl, alkyl moiety. contains from 1 to 20 carbon atoms, from 1 to 20 carbon atoms in the alkyl moiety, from 1 to 20 carbon atoms by the phenyl halogenoalkyl group, from 2 to 20 in the alkenyl moiety, preferably from 2 to 20 carbon atoms. up to 12 carbon atoms, substituted phenyl-alkenyl having 2 to 20, preferably 2 to 12 carbon atoms in the alkenyl moiety, wherein the substituents are selected from the group consisting of halogen atoms, alkyl groups having from 1 to 20 carbon atoms and alkoxy groups from 1 to 20 carbon atoms, halo-phenoxy, phenylalkoxy having 1-20 carbon atoms in alkoxy, phenylalkylcarboxy-alkyl in which each alkyl moiety contains from 1 to 20 carbon atoms, phenylcycloalkyl having no more than 20 carbon atoms in cycloalkyl halo-phenylalkenyloxy having 2 to 20, preferably 2 to 12, carbon atoms in the alkenyl moiety, halothiophenylalkyl of 1 to 20 carbon atoms in the alkyl moiety, a haloenoxyalkyl moiety having 1 to 20 SiB241

With UW atoms in the alkyl moiety, a bicycloalkyl moiety with no more than 2.0 carbon atoms in each cycloalkyl moiety, an alkenylcarbamoylpyridinyl moiety containing 2 to 20, preferably 2 to 12 carbon atoms in the alkenyl moiety, an alkynylcarbamoylpyridinyl moiety containing in alkynyl moiety 2 up to 20, preferably 2 to 12, carbon atoms, diaphenylcarbamoylhicyclaalkenyl, and in each alkenyl moiety 2 to 20, preferably 2 to 12, carbon atoms and in each cycloalkenyl moiety at most 20 carbon atoms; arbamoylbicycloalkenyl having a range of 2 to 20, preferably 2 to 12 carbon atoms in the alkynyl moiety and 20 carbon atoms in each cycloalkenyl moiety, all of which may have direct aliphatic radicals or a branched chain, and each of R 1 and R 2, which may be the same non-different, represents an alkenyl group use 2 to. 20, preferably 2 to 12 carbon atoms, haloalkenyl having 2 to 20, preferably. 2 to 12 carbon atoms, atom. hydrogen, alkyl of 1 to 20 carbon atoms, haloalkyl of 1 to 20 carbon atoms, alkenyl of 2 to 20, preferably 2 to 12 carbon atoms, cyanoalkyl of 1 to 20 carbon atoms in alkyl part, a hydroxyalkyl group having 1 to 20 carbon atoms, a hydroxyhaloalkyl group having 1 to 20 carbon atoms, a haloalkyl-carboxyalkyl group having in each alkyl moiety 1 to 20 carbon atoms, an alkylcarboxyalkyl group containing in each alkyl moiety 1 to 20 carbon atoms, an alkoxycarboxyalkyl group containing from 1 to 20 carbon atoms in both alkoxy and alkyl moieties, a thioalkylcarbonylalkyl group having in each alkyl moiety 1 to 20 carbon atoms, an alkoxycarbonylalkyl moiety having an alkoxy moiety; the alkyl moieties are each; 20 carbon atoms, alkylcarbamoyloxyalkyl containing in each alkyl moiety 1 to 20 carbon atoms, amino, rharmyl, haloalkyl-N-allylamido having 1 to 20 carbon atoms in each alkyl moiety, halogen -alkylamido-alkyl having 1 to 20 carbon atoms, haloalkylamido-alkyl having 1 to 20 carbon atoms in each alkyl, halogen-alkyl-N-alkylamidoalkyl having 1 to 20 carbon atoms in each alkyl moiety , (C 1 -C 20) -alkyl halogenoalkyl amidoalkenyl, (C 2 -C 2) alkylimino, C 2 -C 20 alkylimino, C 1 -C 5 alkylcycloalkyl in the alkyl moiety of 1 to 20 carbon atoms and in the cycloalkyl moiety the highest C20, alkoxyalkyl having 1 to 20 carbon atoms in the alkoxy and alkyl moieties, alkylsulfonyloxy. with an alkyl group having in each alkyl moiety 1 to 20 carbon atoms, a mercaptoalkyl group having 1 to 20 carbon atoms, an alkylaminoalkyl moiety containing in each alkyl moiety 1 to 20 carbon atoms, an alkoxycarbanylalkylene moiety -pine containing, in the alkoxy portion of 1 to 20 atoms, carbon and in the alkenyl portion 2 to 20, preferably 2 to 12 carbon atoms, haloalkyl-carbonyl having 1 to 20 carbon atoms in the alkyl, alkylcarbonyl group having 1 to 20 carbon atoms in the alkyl portion; the alkenylcarbamoyloxyalkyl group containing the alkenyl moiety. From 2 to 20, preferably from 2 to 12 carbon atoms, and from 1 to 20 carbon atoms, cycloalkylcarbamoyl-oxyalkyl, and having from 20 to 20 carbon atoms in the cyclone-alkyl group and an alkyl group having from 20 to 20 carbon atoms; C 1 -C 20 alkoxy, C 1 -C 20 haloalkoxycarbonyl, C 1 -C 20 alkylphenylcarbamoyloxy-alkyl, C 20 cycloalkenyl, phenyl a substituted phenyl group wherein the substituents are selected from the group consisting of C 1 -C 20 alkyl groups, halogen atoms, C 1 -C 20 haloalkyl groups, C 1 -C 20 alkoxy groups, C 1 -C 20 haloalkylaraalkyl groups (C 1 -C 20) -alpha-amido groups having from 1 to 20 carbon atoms in the alkyl moiety Alkylcarbamoyloxy having 2 to 20, preferably 2 to 12 carbon atoms in the alkenyl moiety, C 1 -C 20 alkyl amido groups, C 1 -C 20 haloalkylamido groups and alkylcarbonylalkenyl groups containing from 1 to 20 carbon atoms and in the alkynyl moiety from 2 to 20, preferably from 2 to 12 carbon atoms, a phenylcarbonyl group, a phenylalkyl group having from 1 to 20 carbon atoms in the alkyl moiety, a substituted phenylalkyl group having from 1 to 20 carbon atoms, 20 carbon atoms in the alkyl moiety wherein the substituents are selected from the group consisting of halogen atoms, C 1 -C 20 alkyl groups, dioxyalkylene groups having from 3 to 20 carbon atoms in the alkylene moiety, and haloenoxyalkylamidoalkyl moieties containing in each case carbon atoms; alkyl of 1 to 20 carbon atoms, alkylthiodiazolyl of 1 to 20 carbon atoms of the alkyl moiety, piperidylalkyl group C 1 -C 20 alkyl, thiazolyl, C 1 -C 20 alkylthio, benzothiazolyl, halo benzothiazolyl, C 1 -C 20 furyl alkyl , a pyridyl group, an alkylpyridyl group having from 1 to 20 carbon atoms in the alkyl, an alkyloxazolyl group having from 1 to 20 carbon atoms in the alkyl part, a tetrahydrofuryl group of from 1 to 20 carbon atoms in the alkyl group, a 3-cyano group; 4,5-polyalkylene-thienyl of 1 to 20 carbon atoms in each alkylene moiety,--haloalkyl-acetyl-dophenylalkynyl group having in each alkyl moiety 1 to 20 carbon atoms, α-haloalkylacetamidonitrophenylalkyl group containing from 1 to 20 carbon atoms in each alkyl moiety; and a-halo-alkyl acetamidohalophenylalkyl group containing from 1 to 20 atoms in each alkyl moiety kyánoálkenylovouskupinu alkyl or alkenyl moiety containing 2 to 20, preferably 2 to 12 carbon atoms, or

R 1 and R 2 together may form a piperidinyl radical, an alkylpiperidinyl radical having from 1 to 20 carbon atoms in the alkyl, an alkylthihydrhydropyridyl radical of from 1 to 20 carbon atoms in the alkyl radical, a morpholyl radical, an alkylmorpholyl radical of from 1 to 20 carbon atoms in the alkyl radical , an azobicyclononyl radical, a benzoalkylpyrrolidinyl radical having from 1 to 20 carbon atoms in the alkyl, an oxazolidyl radical, an alkyloxazolidyl radical having from 1 to 20 carbon atoms in the alkyl radical, a perhydroquinolyl radical or an alkylamino-alkenyl radical containing from 1 to 20 in the alkyl radical carbon atoms and alkenyl moiety 2. with from 20 to 20 carbon atoms, preferably from 2 to 12 carbon atoms, all of the abovementioned aliphatic radicals R 1 and R 2 being straight or branched, provided that when R 1 is hydrogen, R 2 is other than hydrogen or halogen.

The compounds of the above general formula (I) may be prepared by mixing the corresponding acid with the corresponding amine. The reaction may optionally be carried out in a solvent such as benzene. The reaction is preferably carried out at a lower temperature. After completion of the reaction, the reaction product is not allowed to warm to room temperature and can be readily isolated.

The antidepressant compounds of the present invention can be used in any conventional form. Thus, the antidotes can be processed into emulsifiable liquids, emulsifiable concentrates, liquid formulations, powders, wettable powders, granules or other conventional formulations. Preferably, the antidotes are mixed with thiolcarbamates and incorporate sediment before or after sowing the seeds. It should be emphasized that the thiolcarbate type herbicide can be applied to the soil first and then applied to the soil. Further, the antidote can be treated axially, and then sown into the soil treated with the herbicide or into the soil untreated and then treated with the herbicide to heat the soil. The method of adding an antidote does not affect the herbicidal activity of carbamate-type derivatives.

The antidotes may be used in amounts ranging from 0.0001 to 30 parts by weight per herbicide. The antidote is generally governed by economic considerations. The term "herbicidally active compound" blends the active thiolcarbamates either alone or in admixture with other active compounds such as s-triazines and 2,4-D, active acetanilide derivatives, and the like. The herbicidally active compound is different from the antidote.

It is clear that the individual classes of herbicidal agents disclosed in the description and examples show herbicidal activity. However, the degree of this herbicidal activity varies depending on the individual specific compounds in these classes and their combinations. Similarly, the levers vary in degree of effect, depending on the hosts to which a particular herbicidal agent or combination thereof may be applied. Accordingly, it is easy to select a specific herbicidal compound or appropriate combination suitable for controlling an undesirable plant species. In accordance with the invention, damage to desired crop plants due to the presence of a specific compound or combination thereof can be avoided;

The crops which can be protected by the process according to the invention are not limited by the specific crop plants exemplified.

The herbicidal substances used in the process of the invention are herbicidally active substances acting in general, i.e. the individual compounds of this group are herbicidal. effective against a wide variety of plant species, regardless of whether they are desirable or undesirable. The method of controlling the growth involves application of a herbicide. an effective amount of the herbicides described above for the area or location of the fungal plants.

As used herein, the term "herbicide" refers to a compound that kills or modifies the growth of a particular plant or individual plant. These effects include all deviations from natural development, such as eradication, growth inhibition, defoliation, drying out, growth and development regulation, stunted growth, expulsion of stems, stimulation of growth, development of deformed individuals, and the like. in a broader sense, they mean germinating plants, emerging cotyledons or mature plants, including roots and aboveground particles.

The herbicides listed in the tables are used in doses leading to effective extermination of undesirable vegetation. These doses range from those recommended by the supplier. Thus, weed control is in any case commercially acceptable in the desired range. All of the above-mentioned aliphatic radicals may be straight-chain or branched, wherein the alkenyl radicals each contain at least one olefinic double bond and the alkynyl radicals each contain at least one acetylene radical bond.

The invention is illustrated by the following non-limiting examples. 19 6 2 4 '1 10 Example 1 O CH2 - CH = CH2 II /

CHC12-C-N-CH2-CH-CH2

By dissolving 3.7 g (0.025 mol) of dichloroacetyl chloride in 100 ml of methylene dichloride, a solution is prepared which is then cooled to about 5 ° C in ice and 4.9 g (0 g) are added dropwise while maintaining the temperature below about 10 ° C. .05 mol) of di-allylamine. The mixture was stirred at room temperature for about 4 hours, then washed twice, dried over magnesium sulfate, filtered and evaporated. The product yield was 4.0 grams; n D 3 = 1.4990. Example 2 O C3H7-n II /

CHC12 — C — N. C3H7-n

By dissolving 3.7 g (0.025 mol) of dichloroacetyl chloride in 100 ml of methylene dichloride, a solution is prepared which is then cooled to about 10 ° C in ice and 5.1 g (0.05 moles) are added dropwise thereto while maintaining the temperature below 10 ° C. ) di-n-propylamine. The mixture was stirred overnight at room temperature, then washed twice with water, dried over magnesium sulfate, filtered and evaporated. Yield 3.6 g; nD3 '= 1.4778. Example 3 About CH3II /

CHC12 — C — N \ t

CH (CH 3) -C-CH

Dissolve 3.7 g (0.025 mol) of dichloroacetyl chloride in 80 ml of methylene dichloride to prepare a solution which is then cooled to 10 ° C in ice and a solution of 3.2 g (0.05 mol) is added dropwise while maintaining the temperature at about 10 ° C. N-methyl-N1-methyl-3-propynylamine in 20 ml of methylene dichloride. The mixture was stirred at room temperature for 4 hours, washed twice with water, dried over magnesium sulfate, filtered and evaporated to yield 2.9 g; nD20 = 1.4980. Example 4

CWjCt -C

A solution of 5.05 g (0.1 mol) of furfurylamine in 100 ml of acetone is stirred with 15 ml of triethylamine at 15 DEG C., then 5.7 g of monochloroacetyl chloride are added, and the mixture is stirred for 15 minutes. mlvody. The reaction mass is filtered, washed with dilute hydrochloric acid and water, and then dried to constant weight. Example 5 in - - ''

A solution containing 5.7 g (0.05 mol) aminomethylthioazole in 100 ml benzene and 7 ml triethylamine was prepared. This solution is stirred at 10-15 ° C and 5.2 ml (0.05 mol) of dichloroacetyl chloride is added dropwise. The reaction mixture is stirred at room temperature for 10 minutes, then 100 ml of water are added. the wash was dried with magnesium sulfate and after filtration the solvent was evaporated. Example 6 o / CHCl3

Br A solution consisting of 200 acetone, 17.5 g (0.05 mol) of 2-amino-6-bromobenzothiazole and 7 ml of triethylamine was prepared. The solution is cooled to 15 ° C with stirring and 5.2 ml (0.05 mol) of di-chloroacetyl chloride is added slowly. The reaction mixture was stirred at room temperature for 10 minutes, the resulting solid product was filtered off, washed first with ether and then with cold water, and then dried at 40-50 ° C by dip filtration. Example 7

O H II- / n-CgHio — C — N \ t

C (CH3) 2-CsCH 3.4 g of 3-methyl-3-butylamine are dissolved in 50 ml of methylene chloride, 4.5 g of triethylamine are added to the solution, followed by 7.6 g of stirring on water bath. decanoyl chloride. After completion of the reaction, the mixture is washed with water, dried and, after evaporation of the solvent, 7.1 g of the desired product is obtained. 5.9 g of diallylamine are dissolved in 15 ml of methylene chloride and 6.5 g of triethylamine, and 6.3 g of cyclopropanone carbonyl is then added dropwise to the solution while stirring and cooling to water. After the reaction is complete, the mixture is washed with water, dried and, after evaporation of the solvent, 8.2 g of the desired product are obtained. /

CHC12 — C — N

CH 2 —CH 2 —O

O-C-NH-CH 3 Example 9 CH 2 -CH 2 -O-C-NH-CH 3

A solution containing 4.5 g of diallyl amine dissolved in 15 ml of methylene chloride and 5.0 g of trlethylamine was prepared. 7.1 g of o-fluorobenzoyl chloride are added dropwise to the solution under stirring and cooling in a water bath. After completion of the reaction, the mixture is washed with water, dried and, after evaporation of the solvent, 8.5 g of the desired product are obtained;

O

By reacting 26.3 g of diethanolamine with 37 g of di-chloroacetyl chloride in the presence of 25.5 g of triethylamine in 100 ml of acetone, Ν-bis (2-hydroxyethyl) dichloride acetamide was prepared. 6.5 g of N, N-bis (2-hydroxyethyldichloroacetamide) are dissolved in 50 ml of acetone and treated with 4 g of methyl isocyanate in the presence of dibutyltin dilaurate and triethylamine as catalysts. , 4 g of the desired product.

CH2 = CH-CH2 O: O \ II II / N-C-CH2-C-N / \ CH 2 = CH-CH 2 CH 2 CH = CH 2 CH = CH 2 7.8 g of diallylamine was dissolved in 50 ml of me- of thylene chloride with dropwise addition of 8.5 g of triethylamine. While stirring and cooling, 5.6 g of malonyl chloride are added, after completion of the reaction, the mixture is washed with water, dried over magnesium sulphate and 7.0 g of the desired product are obtained after evaporation in vacuo. EXAMPLE 1 CH 2 = CH — CH 2 CH 2 —CH = CH — CH — CH 2 —C — N — CH 2 CH = CH-CH 2 7.9 g of diallylamine was dissolved in 50 mL of methylene chloride dropwise. 8.5 g of triethylamine. 6.2 g of succinic chloride are then added dropwise with stirring and cooling, and the reaction mixture is washed with water.

CH3 O, I. .. "II.

CH = C-CH-N-C-CH2-CH2-C-NI-CH3 6.7 g of N-methyl-1-methyl-3-propionylamine dissolved in 50 ml of methylene chloride dropwise with 8.5 g of triethylamine . 6.2 g of succinic chloride are then added dropwise with cooling and stirring and after completion of the reaction, it is combined with water, dried over magnesium sulphate and evaporated in vacuo. 7.0 g of the desired product are obtained. CH2-CH-CH2 dried over magnesium sulfate and evaporated in vacuo. 9.7 g of the desired product are obtained. EXAMPLE 13 CH3

CH-CsCH CH3 Example 1 4

C-N O = C-N (CH 2 CH-CH 3%)

7.9 g of diallyl amine are dissolved in 50 ml of methylene chloride dropwise with 8.5 g of triethylamine. 8.1 g of o-phthaloyl chloride are then added dropwise with cooling and stirring and after completion of the reaction, the mixture is washed with water, dried over magnesium sulphate and evaporated in vacuo; 10.9 g of the desired product are obtained. Example 15

3.3 g of N-methyl-1-methyl-3-propionylamine are dissolved in 50 ml of methylene chloride with dropwise addition of 4.5 g of triethylamine. Diphenylacetyl chloride (9.2 g) was added dropwise with stirring and the reaction mixture was washed with water, dried (MgSO4) and evaporated in vacuo. 9.9 g of the desired product are obtained. Example 16

Q-K

O = C-OH CH, -CH = CH, 4.9 g of diallyl amine are dissolved in 50 ml of acetone and 7.4 g of phthalic anhydride are added portionwise with stirring. Evaporation of the solvent in vacuo gave 13.0 g of the desired product. Example 17

I J

NW-C-CsCH O = C-ON & 9.2 g of N- (1,1-dimethyl-3-propynyl) -O-phthalic acid are dissolved in 50 ml of methanol and 9.6 g of sodium methoxide (25% by weight) is added to the solution with stirring and cooling. in methanol). Evaporation of the solvent in vacuo gave 9.0 g of product.

The N- (1,1-dimethyl-3-propynyl) -O-phthalamic acid intermediate was prepared from 29.6 phthalic anhydride and 16.6 g of 3-amino-3-methylbutainin in 150 ml of acetone. The intermediate was precipitated with petroleum ether as a white solid which was used without further purification

7.7 g (0.105 mol) of diethylamine, 4.0 g of sodium hydroxide solution and 100 ml of methylene chloride are introduced into a 500 ml 500 ml flask equipped with a stirrer, thermometer and dropping funnel. The mixture was cooled in a solid carbon dioxide bath in acetone and 14.7 g (0.10 mol) of dichloroacetyl chloride was added portionwise. The reaction mixture is stirred for an additional hour, immersed in an ice bath, the phases are separated, the organic phase is washed twice with 100 ml of dilute hydrochloric acid and twice with 100 ml of sodium carbonate solution each time, dried over magnesium sulphate and concentrated in vacuo. 16.8 g of product are obtained. Example 19 CH 2 - CH = CH 2

ch3 — esc— (5h 2 — O — C — N 2 Ch 2 -CH 2 CH 2)

Add 4.0 g (0.025 mol) of Ν, Ν-diallylcarbamoyl chloride to 50 ml of methylene chloride and add dropwise 1.8 g (0.025 mol) of 2-butin-1-ol together with 2.6 g of triethylamine in 10 ml of methanol. methylene chloride. The reaction mixture was stirred overnight at room temperature, then washed twice and dried over magnesium sulfate to give 4.0 g of the desired product. Example 20 CH 2 —CH = CH 2

9.7 g (0.1 mol) of potassium thiocyanate are dissolved in 100 ml of acetone and 8.7 g (0.05 mol) are added to the solution at room temperature. Dial-diallylchloroacetamide with 10 ml dimethylformamide. The reaction mixture was stirred overnight, then partially evaporated. The residue was added with two portions (100 ml) of ether, the ether phase separated, dried and evaporated to give 7.2 g of the desired product. Example 21

CHCl 3 -C-NH-CH 2 H 5

CHC12-C-N C2H5 CH, 7.4 g (0.05 mol) of dichloroacetyl chloride are dissolved in 50 ml of benzene and 3.0 g (0.05 mol) of cyclopropylamine are added to the solution at 5 to 10 ° C and 5.2 g of triethylamine in 2 ml of iodine benzene, precipitate precipitating. The mixture was stirred at room temperature for 2 hours and then at 50-55 ° C for one hour, after which it worked up analogously to the previous example. 5.7 g of the desired product are obtained. Example 2 2

. OII CHCl 2 C-1

4.4 g (0.03 mol) of piperonylamine and 1.2 g of sodium hydroxide in 30 ml of methylene chloride and 12 ml of water are added to a mixture of 4.7 g (0.032 mol) of piperonylamine and 1.2 g of sodium hydroxide. The reaction mixture was stirred at 0 ° C for 10 minutes, then allowed to warm to room temperature with stirring, the layers were separated, the organic layer was washed with dilute hydrochloric acid, 10% carbonate solution. sodium and water, and after drying, 5.9 g of the desired product are obtained.

O

5.7 g of m-chlorocinnamoyl chloride was dissolved in 75 ml of benzene and 3.2 g of diallylamine and 3.3 g of triethylamine in 2 ml of benzene were added to the solution at 5-10 ° C, precipitating precipitate. The reaction mixture was stirred for 2 hours at room temperature and then for 1 hour at 55 ° C, then washed and worked up to give 5.8 g of the desired product. 16

2,4-dimethylpiperidine (11.9 g), sodium hydroxide (4.0 g) and methylene chloride (100 ml) were charged into a 500 ml 4-necked flask equipped with stirrer, thermometer and dropping funnel. The mixture is cooled in a solid carbon dioxide bath in acetone and 14.7 g (0.10 mol) of dichloroacetyl chloride is added in several portions and the reaction mixture is stirred for 1 hour, immersed in an ice bath, the lower organic phase is separated, washed Dilute hydrochloric acid (2 x 100 mL) with 5% carbonate (2 x 100 mL), dry over magnesium sulfate, and concentrate in a rotary evaporator under vacuum to give 19.3 g of the desired product. C -N,

14.6 g (0.105 mol) of cis-trans-decahydroquinoline, 4.0 g of sodium hydroxide solution and 100 ml of methylene chloride are introduced into a 500 ml 500 ml 4-necked flask equipped with a stirrer, thermometer and dropping funnel, followed by 14.7 g of di-chloroacetyl chloride are added in portions. The reaction mixture is worked up by cooling with ice for about one hour, the phases are separated, the lower organic phase is washed twice with 100 ml of dilute hydrochloric acid each time, twice with 100 ml of 5% sodium carbonate solution each, then dried over magnesium sulphate. and evaporated to give 22.3 g of the desired product. Example 24 q CHCl-C-N,

and·,. Example 26 O, O. CH 2 -CH 2 -CH 2 -NH-C-CHCl 2 II /

CHCl 2 -C-N CH 2 -CH 2 -CH 2 -NH-C-CHCl 2

196241 17

13.6 g (0.104 mol) of 3,3'-iminobis-propylamine together with 12.0 g of sodium hydroxide solution and 150% of sodium hydroxide are introduced into a 500 ml 500 ml flask equipped with a stirrer, thermometer and dropping funnel. ml of methylene chloride. The mixture was cooled in an acetone-containing solid carbon dioxide bath and 44.4 g (0.300 mol) of dichloroacetyl chloride was added in portions, leaving an oily product insoluble in methylene chloride. The product was separated, washed twice with 100 ml of dilute acid each time. The mixture was washed with 5% sodium carbonate solution (2 x 100 ml), then extracted with ethanol (100 ml), dried (MgSO4) and concentrated. 21.0 g of the desired product are obtained. Example 27

O

11 uCtCarC-N

7.5 g (0.0525 mol) of tetrahydrofurfuryl-n-propylamine, 2.0 g of sodium hydroxide solution and 100 ml are charged into a 500 ml 500 ml flask equipped with a stirrer, thermometer and dropping funnel. methylene chloride. 7.4 g (0.05 mol) of dichloroacetyl chloride are added in portions, the reaction mixture is stirred for a further hour with cooling and then the lower organic phase is separated. The organic layer is washed twice with 100 ml of dilute hydrochloric acid and twice with 100 ml each. 5% carbonate solution, dried over magnesium sulfate and concentrated to give 12.7 g of product. Example 2 8 18

3.2 g of benzaldehyde and 7.7 g of dichloroacetamide are mixed with 100 ml of benzene and about 0.05 g of p-toluenesulfonic acid. The mixture was refluxed until water was no longer present. After cooling, the desired product crystallizes out of the benzene in a yield of 7.0 g

W un-ii | 3

C-WW-C-C 5 CH

CH3 2.5 g of 3-amino-3-methylbutin are dissolved in 50 ml of acetone, 3.5 g of triethylamine are added first and 6.0 g of adamantane-1-carbonyl chloride are then added dropwise with stirring. The reaction mixture is poured into water, the solid product is filtered off and, after drying in a vacuum, 6.5 g of the desired product are obtained. Example 3 2 cwa

Ns-C-C-NH-C

I ch3

ch3 O I J |

N = C-C-WH-C

The desired product was prepared analogously to Example 27 using 8.9 gpiperidine. Example 29 5.1 g of 2-cyanoisopropylamine. 50 ml of acetone were added with 6.5 g of triethylamine and 5.3 g of benzene-1,3,5-tricarboxylic acid chloride were added dropwise with stirring and cooling. The reaction mixture is poured out, the solid product is filtered off and dried under vacuum to give 7.6 g of the desired product. O t · 1 '' v Example 33 C-NøCH £ CH = CH 2 x c-wi-ch = cwj, II *

O

The desired product was prepared analogously to Example 28 using 9.1 g morpholine. 6.0 g of diallylamine are dissolved in 50 ml of methylene chloride, 6.5 g of triethylamine are added, and 6.6 g of 3,6-endomethylene-1,2,3,6-tetrahydro is added dropwise with stirring and cooling. -phthaloyl chloride. After completion of the reaction, it is taken up in water, dried over magnesium sulphate and, after evaporation in vacuo, 9.3 g of the desired product are obtained. chloroacetyl chloride. The reaction mixture is stirred for about an hour under ice-cooling, then the phases are separated, the lower organic phase is washed twice with 100 ml of dilute hydrochloric acid each time and twice with 100 ml of 5% sodium carbonate solution, dried over magnesium sulphate and then concentrated to give 9. 5 g of the desired product. Example 37

O

CH-CH-

4.0 g of diallylamine are dissolved in 50 ml of methylene chloride, 4.5 g of triethylamine are added first and 7.2 g of trans-2-phenylcyclopropanecarbonyl chloride are then added dropwise with stirring. After completion of the reaction, the mixture was washed with water, dried over magnesium sulfate and evaporated in vacuo to give 9.3 g of product. Annex 3 3

A solution containing 4.0 g (0.03 mol) of 2-methylindoline, 7.0 ml of triethylamine and 100 ml of methylene chloride was prepared. 2.9 ml of dichloroacetyl chloride was added to the tomo-solution while maintaining the temperature below 0 ° C (solid carbon dioxide cooling), the resulting solution was allowed to warm to room temperature, washed with water and dilute hydrochloric acid after standing for 1 hour, dried over magnesium sulfate and evaporated to give a solid material, which was washed with n-pentane to give 5.0 g of product. Example 36

7.8 g (0.0525 mol) of p-methylbenzylethylamine, 2.0 g of sodium hydroxide solution and 100 ml of methylene chloride are introduced into a 500 ml 500 ml flask equipped with a stirrer, thermometer and dropping funnel. Chloroacetyl chloride (5.6 g, 0.05 mol) was added in portions and the reaction mixture was stirred with cooling for about 1 hour, then the phases were separated. the organic phase is washed twice with 100 ml of dilute hydrochloric acid and twice with 100 ml of 5% sodium carbonate solution each time, dried over magnesium sulphate and, after concentration, 9.5 g of the desired product.

4.7 g of aminopyridine and 100 ml of acetone are added to the reaction vessel, 7.0 ml of triethylamine are added dropwise to the mixture at 10 to 15 ° C, then 5.25 ml of dichloroacetyl chloride in 10 ml are added over 5 minutes. and the reaction mixture is stirred at room temperature. The solid product is filtered off and washed with acetone to give 10.0 g of the desired product. Appendix 3 9

8.9 g of cyclooctyl-n-propylamine, 2.0 g of sodium hydroxide solution and 100 ml of methylene chloride are added to a 500 ml 4-necked flask equipped with a stirrer, thermometer and dropping funnel, and the mixture is cooled in a solid oxide bath

O

8.1 g (0.05 mol) of 4-aminophthalimide are dissolved in 100 ml of dimethylfuran, and 5.0 g of chloroacetyl chloro-21 196241 du are added to the solution first with stirring at 0 to 10 ° C. and then 7.0 ml of triethylamine are added. The reaction mixture was stirred at room temperature for half an hour and then 1 liter of water was added. Filtration and drying gave 12.0 g of the desired product. 22 milliliters of acetone and dibutyltin dilaurate and triethylenediamine as catalysts. The reaction mixture was heated to reflux and, after evaporation in vacuo, afforded 6.9grams of the desired product. Example 40

O II · O CH 2 —CH 2 —O — C — NH — C 3 H 7 —I /, ·,,

CHCl 2 —C — N Example 42 CWC t £ CH 2 —CH 2 —O — C — NH — C 3 H 7 —I

The desired product is prepared by reacting 5.4 g of s-blots of (2-hydroxyethyl) dichloroacetamide with 4.3 g of isopropyl isocyanate in 50 ml of acetone in the presence of dibutyltin dilaurate and triethylene diamine as catalysts. 8.2 g of product are obtained. Example 41 o

The desired product is prepared by reacting 3.0 g of bis-bis (2-hydroxyethyl) chloroacetamide with 5.0 g of cyclohexyl isocyanate in the presence of 50% of cyclohexyl isocyanate. g of acetone and 12.2 g of ethanolamine are mixed in 150 ml of benzene, and the mixture is refluxed until no more water is present. According to the analysis, the resulting solution contains 2,2-dimethyl-1,3-oxazolidine. A quarter of the benzene solution (0.05 mM) was treated with 4.7 g of dichlorobutyl chloride and 5.5 g of triethylamine, washed with water and dried and evaporated in vacuo to give a slightly yellowish-colored solid residue. Recrystallization of the residue from ether gave a white product.

Other compounds were prepared analogously to the above starting materials. Representative compounds of the invention are shown in the following table. Each of the compounds in Table 0 is numbered. These numbers are used to identify the respective compounds in the following application. 198241 O Ri 11 '/ R-C-N R2

Compound No. R 1 R 2 R 1 -CH (CH 3) Br — CH 2 —CH = CH 2 —CH 2 —CH = CH 2 —C (CH 3) 2 Br — CH 2 —CH = CH 2 —CH 2 —CH = CH 3 —CCl 2 —CH 3 - CH 2 -CH = CH 2 -CH 2 -CH = CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH = CH 2 -CH 2 -CH = CH 2 -CH 2 -CH 2 -CH 2 -CH = CH 2 -CH 2 -CH = CH 2 -CH 2 -CH = CH 2 -CH 2 CH 2 -CH 2 -C = N-CH 2 -C = N 9 -CHCl 2 -CH 2 -CH = CH 2 '; H 10 —CHCl 2 —C 3 H 7 -C 3 H 7 11 —CHCl 2 —C (CH 3) 2 —C = NH 12 —CH 2 Cl — C (CH 3) 2 —C = NH 13 —CCl 3 —CH 2 —CH = CH 2 H 14 —CCl 3 —CH 2 -CH = CH 2 -CH 2 -CH = CH 2 15 -CH 2 Cl-C (CH 3) 2 -Ch = CH H 16. —CHG1Z — C— (CH3J2 — C = GH H 17 —CC13 — C (CH 3) 2 —CCHCH 18 —CHCl2 — CH 3 —CH (CH 3) —c = ch 19 —CHCl 2 —CH 2 —CH = CH 2 20 -CH 2 Cl 2 21 -CHCl 2 H -cwApA 22

—CH 2 Cl

H 22

—CH 2 Cl 2 —CHCl 2 24 25 —CHCl 2 —CHCl 2 26 —CHCl 2 27 —CHCl · 28 CHCl 2

Compound 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 4849 '50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 196241

R Ri Rz 0 II. - C - O - C 2 H 5 O - CH 3 --CH (CH 3) - C 5 CH 5 - C 0 - C 2 H 5 --CH 2 --CH = CH 2 --CH 2 --CH = CH 2 -CH 2 --CH (CH 3) - CH 2 -t-C 6 H 5 H —C (CH 3) 2 — C = CH — C (CH 3) 2 —C 3 H 7 —CH 2 —CH = CH 2 —CH 2 —CH = CH 2 —CH 2 —t — C 4 H 9 —CH 3 —CH (CH 3) —CsCH — CH 2 —t —C4H9 H — C (CH3) 2 —CNN — CH2CH3 — C3H7 —CH2 — CH = CH2 · —CH2 — CH = CH2 —CH2CH5 —C3H7 —CH3 — CH (CH3) —C = CH — CH (CH3) - C 3 H 7 H — C (CH 3) 2 —C = CH 1 -C 8 H 7 —CH 3 —CH (CH 3) - C = CH — C 13 H 27 —CH 2 —CH = CH 2 —CH 2 —ch = ch 2 —C 11 H 23 —CH 2 —CH = CH 2 - CH 2 -CH = CH 2 -C 11 H 23 H — C (CH 3) 2 —C = CH — C 9 H 19 —CH 2 —CH = CH 2 —CH 2 —CH = CH 2 —C 9 H 19 H — C (CH 3) 2 — CsCH — C 6 H 13 —CH 2— ch = CH 2 -CH 2 -CH = CH 2 -C 6 H 13 -CH 3 -CH (CH 3) -C 5 CH-C 6 H 13 C (CH 3) 2 -C = CH-C 4 H 9 H-C (CH 3) 2 -C = CH-C 3 H 7 -CH 2 -CH 3 -CH 2 -CH = CH 3 -CH 3 -CH 3 -CH (CH 3) -C 5 CH-C 3 H 7 H -C (CH 3) 2 -C = CH-CH 3 -CH 2 -CH = CH 2 -CH 2 -CH = CH 2 —CH 3 H -C (CH 3) 2 —CSCH — C (CH 3) = CH 2 H — C (CH 3) 2 —c = ch — CH = CH -CH 3 -CH 2 -CH = CH-CH 3 -CH (CH 3) 2 -C = CH-CH = C (CH 3) 2 -CH 3 -CH (CH 3) -CH 3 -CH = C (CH 3) 2 H — C (CH 3) 2 —C = CH — CH = CH — CH = CH — CH 3 —CH 2 —CH = CH — CH 2 —CH = CH 3 —CH = CH-CH = CH — CH 3 H —C (CH3) z —CCHCH - 1 —CH2 — CH = CH 2 —CH 2 —CH = CH 2 • —CH 3 —CH (CH 3) —C = CH — CH · H — C (CH 3) 2 —CCHCH — CH 2 — CH = CH 2 -CH 2 -CH = CH 2 -CH 2 -CH (CH 3) -CH 2 CH-C (CH 3) 2 -CHCH

-CH 2 -CH = CH 2 -CH 3 -CH 2 -CH = CH 2 -CH 2 -CH = CH 2

- CH (CH 2) - C = CH - CH 2 - CH = CH 2 --CH 3 --CH (CH 3) - c = ch 69

Compound No.

R

R1 R2 13B241 70 7 72 73 74 75 76 77 78 79 -CH = CH 2 -CH = CH 2 '

-CK ΚΞ>

—C (CH 3 12 —C = CH — CH 2 —CH = CH 2 —CH 2 —CH = CH 2)

—CH 3 —CH [CH 3] —C = CH

H - C (CH 3) 2 - CsGH - n - CH = CH 2 - CH 2 - CH = CH 2 --CH 3 - CH [CH 3] - c = ch

H — C (CH 3) 2 —C = CH — CH 2 —CH = CH 2 —Ci 2 —ch = ch 2 —CH 3 —CH 3

—CH (CH3) —CsCH

—CH (CH 3) —C = CH 80 H — C (CH 3) 2 —C = CH 81 I —CBr 3 —CH, 2 —CH = CH 2 —CH 2 —CH = CH 2 82 —CBr 3 —CH 3 —CH (CH 3) - CsCH 83 —CBn H — C (CH 3) 2 —c = ch 84 —CBr 3 H — C (CH 3) 2 — C = N 85 —CBr 3 H — CH 2 —ch = ch 2 86 —CCl = CHC 1 - CH 3 —CH (CH 3 - CH = CH 2 CH 4 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 4 CH 2 CH - CH 3 CH 3 CH 3 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 -CH 2 -CH = CH 2

Cl 90 91 92 93 94 / Λ

Cl v

— Cl - CH 3 - CH 3

—CH (CH 3) —C = CH

-CH (CH 3 -CH 2 -CH 2 -CH = CH 2 -CH 2 -CH = CH 2)

—CH 3 —CH (CH 3) —C = CH

H — C (CH 3) 2 —C = CH

Compound No. 95 96 97 98 99 100 101 102 103 104 105 106 107 108 109

196241

R 1 -CH 2 -CH = CH 2

H — CH 3

H — C.H3

H — CH 3

H — CH 2 —CH = CH 2 —CH 3 —CH 2 —CH = CH 2 —CH 3 —CH 3 R 2 —CK 2 —CH = CH 2

- C (CH 3) 2 -C 5 CH - CH (CH 3) - c = ch

- C (CH 2) 2 - CsCH

-CH (CH 3) -C 5 CH -c (CH 3) 2-g = ch

—CH (CH3) —OCH

—C (CH 3) 2 —CSCH — Ct 2 —CH = CH 2

—CH (CH3 — C ^ CH — CH2 — CH = CH2 —CH (CH3) - c = ch — C {CH3} 2 — c = ch — CH (CH3) - c = ch

—C (CH 3) 2-C = CH 196241

Compound No. 110 111

-CH 3 -CH (CH 3) -CH 2 -CH 2 -CH = CH 2 -CH 2 -CHH-CH 2 112 -CH 3 -CH [CH 3] - c = ch 113 114 115 116

-CH 2 -CH = CH 2 -CH 2 -CH = CH 2

H - C (CH 3) 2 - C = CH - CH 2 - CH = CH 2 --CH 2 - CH = CH 2

H — C (CH 3) 2 —CH 2 CH 117 118 119 120 —CHCl 2 —CHCl 2 —CHCl 2

JQ

-CH 2 CH 2 -O-C-CH 2 -CH 2 -O-C-CH 2 -CHCl 2 -CH 2 -CH 2 -O- —CH 2 —CH — O — SO 2 —CH 3 —SO 2 —CH 3 —CH 3 —CH ( CH3) —c = ch

121

- CH 3 --CH (CH 3) - Ce = CH

122 —CHB — CH 3 —CH 3 —CH (CH 3) —C 8 CH 123 —CHB — CH 3 H — G (CH 3) from —CHCH 124 —CH 2 —CH 2 CH — CH 2 CH = CH 2 —CH 2 —CH = CH 2 125 —CH 2 —CH 2 CH — CH 3 —CH (CH3) —CsCH 126 —CH2 — CH2ClH — C (CH3) 2 —C = CH127 —CBr (CH3) 2H — C (CH3) z — CsCH 128 —CH2I — CH2CH = CH2 —CH2 — CH CH 2 129 —CH 2 —CH 3 —CH (CH 3) - c = ch 130 —CH 2 H — C (CH 3) 2 —C = CH 131 —CHCl 2 —CH 2 —CH 2 Cl — CH 2 —CH 2 Cl 0 11 II II, 132 —CHCl 2 II-CH 2 -CH 2 -O-C-2-CH 2 -CH 2 -O-C-NH-CH 3 -NH-CH 3 -O-II-11-133 -CH 2 -CH 2 -CH 2 -O-C-CH 2 - CH 2 -O — C — O — CH 3 —O — CH 3 O · 11 · 134 —CH 2 CH 2 —CH 2 —O — C —: —CH 2 —CH 2 —O — C — O — C 2 H 5 —C 2 H 5 O II: θ 135 —CHCH 2 · —CH 2 —CH 2 —O — c — CH 2 —CH 2 —O — C — S — C 2 H 5 —S — C 2 H 5

Compound No. R 196241 13Θ. -CH 2 O -CH 2 O -CH 2 O -CH 2 O -CH 2 O -CH 2 O -CH 2 OCH 2 OCH 2 OCH 2 OCH 2 OCH 2 OCH 2 OCH 2 OCH 2 OCH 2 OCH 2 OCH 2 OCH 3 O 145 —CH2 — C — NH — C (CH3)) 2C = CHO 146 || —C — N (CH — — CH = CH2) 2 147 147 —C — N (CH3) —CH (CHS) —C = CH 0 148-C — NH — C (CH 3) 2 —C = CHO II · 149 —CH 2 —CH 2 —C — N (CH 2 —CH = CH 2) 2 O 11 150 -CH 2 —CH 2 —C - N (CH 3) - —CH (CH 3) C = CH 0 151 - (CH 2) 3-CN (CH 2 -CH = CH 2) 2 O 152 || - (CH 2) 3 -C-N (CH 3) -CH (CH 3) - c = CH 3 153 - (CH 2) 4 —C — N (CH 2 —CH = CH 2) 2

R 1 R 2 -CH 2 CH = CH 2 -CH 2 -CH = CH 2

-CH 3 -CH (CH 3) -CH 2 CH

H-C (CH3) 2-CsCH

-CH 2 -CH = CH 2 -CH 2 -CH = CH 2 -GH 3 -CH (CH 3) -CH 3 -CH 2 -CH = CH 2 -CH 2 -CH = CH 2 -CH 3 -CH (CH 3) -c = CH 2 -CH = CH 2 -CH 2 -CH = CH 2

—CH 3 —CH (CH 3) —CsCH

H — C (CH 3) 2 —CSCH — CH 2 —CH = CH 2 —CH 2 —CH = CH 2 —CH 3 —CH (CH 3) —c = ch

H-C (CH 3) 2 -C 5 -CH 2 -CH 2 -CH-CH 2. -CH 2 -CH = CH 2

-CH 3 -CH (CH 3 -CH = CH-CH 2 -CH = CH 2 -CH 2 -CH-CH 2 -CH 3 -CH (CH 3) -c = CH-CH 2 -CH = CH 2 -CH 2 -CH = CH 2 -

Ri

Compound No. R2 0

154 - (CH ' 2) 4-C-N (CH3) -CH3-CH (CH3)-CsCH

—CH (CH3) —CsCH2

155 - C (Cri 3) 2 - C - N (CH 3) - - CH 3 --CH (CH 3 CH 3 -CH 3 CH 3)

—CH (CH3) —C = CHΌ · .11

156 - CH 2 - C (CH 3) 2 - GH 2 - C - ... H - C (CH 3) 2 - C = CH

—NH — C (CH 3) 3 —C = CH

O157-CI-12-O-CH2-C-N [CH 2 -CH 2 -CH = CH 2 -CH 2 -CH 2 -CH 2 -CH = CH 2] 2 by:

158 —CH 2 —O — Q · H 2 —C — N (CH 3) - · · —CH 3. . --CH (CH 3) - C = CH - CH (CH 3) - c = ch 159

OO i (C ^ CNC--C z z)) from - C22-CH =CH CH. - CH 2 - CH = CH 2 160

CH (CH3) -CsCH. o = c N (CH 1 -CH (CH) -CSCHδ ..... - δ 161

-C (CH 3) 2 - CsCH 162 ° ·

WH-CfCW3JA-CsCW

O = C -CH 3 -CH (CH 3) -c = ch

N (CHS) -C H (CH 3) -C CH 3 O

-CH 2 CH = CH 2 -CH 2 -CH = CH 2 o = c

N (CH 2 H = CH 2) Z -C (CH 3) 2 —C — N (CH 2 —CH = CH 2) 2 —CH 2 CH = CH 2 —CH 2 —CH = CH 2

-C (CH3) 2-C-NH-C (CH3) 2-C = CH

—C (CH 3) 2 — CsCH 164 165 196241

168 169 170 171 172 173 174 175

I want _ <G>

•I WANT

-CH 176

-I WANT

CH 2 CH = CH 2 -CH 2 -CH = CH 2

- CH 3 --CH (CH 3) - C 5 CH 3 --C (CH 3) 2 - Cs = CH - CH 3 --h 2 = CH 2 - CH 3 --CH = CH 2 --CH 3 --CHCCH 3 --C 8 H H - C (CH 2) 2 - c -CH 3 -CH (CH 3) -CH 3 -CH 2 CH = CH 2 -CH 2 -CH = CH 2

O = C-OH

O = C-OW »-

-C (CHS) 2 - C = CH

- C (CH 3) 2 - CsCH 177

-D 178 G = CO ~ HHr + CtCH3) -C = CH H - C (CH3) 2 - c = ch 179 - CHCl2 --C2H5 - C2H5 180 - CF1C12 - C3H7 - ch2 - ch = ch2 181 —CHC12 — C3H7 —Ch2 —ch = ch2 182 —chci2 11-C4H9 —ch2 — ch = ch2 183 —CHCH — ch2ch = ch2 —CH2 — cci = ch2 184 —CHCH — C3H7 — ch2 — cci = ch2 185 —CHCH1-C4H9 —ch2 -Ch = CH 2 186 -CH 2 CH 2 -CH 2 -C (CH 3) -CH 2 -CH 2 -CH = CH 2 187 -CH 2 CH 4 -CH 4 sec-C 4 H 9 188 -CHCl 2 -H 4 H 9 -H 4 H 9 189 -CHCl 2 -C 4 H 9 I- C3H7 190 -CH2-C4H9-C3H7 191 -CH3-C4H9 11-C3H7 192 -CH3-C4H9 11-C3H7 196241

Compound No. R

R 1 R 2 193 -CHCl 2 194 -CH 2 CH 2 -NCH 9 n-C 3 H 3 -C 2 H 5 -L-C 4 H 9 195 -CHCl 2

196 197 198 199 200201202 203 204 205 —CHCl2

CH 2 CH 2 O-CH 2 -C = C-CH 2 -O-C 2 H 4 Cl-O-CH 2 -CH 2 CH 3

-CH 2 -S-CsN-CH 2 -N (CH 2 -CH = CH 2) 2 206 -CHCl 2 CH 2 CH 2

O 208 209 210

CH 2 -CH 2 -CH 2 -C = N-CH 2 -O-C = N-CH 3 -NH 2 -CH 2 CH = CH 2 -CH 2 -CH = CH 2 = [N (CH 3) 2] 2 = [N (CH 3) 2] CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH -CH 2 -CH = CH 2 -CH 2 -CH = CH 2 -CH 2 -CH = CH 2

O 'll ·

—N (CH 3) —C — CHCl 2 —CH 3 —N (C — CH 2) 2 —CH 2 —CH = CH 2 —CH 2 —CH = CH 2 —CH 2 —CH = CH 2 —CH 2 —CH = CH — CH 2 —CH = CH 2— CH 2 - CH = CH 2

O 211 212 213 214 —CHCl 2 --CH 2 CH 2 CH 2 -C 2 H 5

—CH2 — CH2 — C = N

H

CH 2 -CH 2 -O-C-CHCl 2 -CH 2 -CH 2 -C = N

-CHCl 2 OCH 2 CH 2 CH 3 CH 3 216 -CH 2 Cl 2 • CH 2 Cl 2 218 c-CH 2 Cl 2 219 -r-CH 2 Cl 2 -CH 2 Cl 2 - CHCl 2 --CH 2 Cl 2

H

H

H

H

-CH 2 -RCH (CH 3) 2

-CH CH, 1-C4H9. 1-C 4 H 9 -I-C 4 H 9 -CH (CH 3) -CH 2 —CH (CH 3) ——CH 3 196241

Ri

Compound No. R

R 2 223 -CHCl 2 224 -CHCl 2 225 '... CH 2 Cl 2 226 -CHCl 2 227 -CHCl 2 228 -CH = CH-d 2 230 230 -CH = CN - ^^ - F 231 r ~ <cl -CH 232 -CHCl2 233 -CHCl2 234 -CHCl2 235 -CHCl2 236 -CHCl2 237 -CHCl2 238 -CHCl2 239 -CH2-SO2-N (CH2-CH = CH2) 240 -CH (S-C2H5) 2,241 -CHCl 2 O 2 242 -CH 2 -O-C-CHCl 2 243 -CH (Ο-ζ -ethyl, 244-CHCl 2 245 -CHCl 2 246 -CHCl 2 247 -CHCl 2 -CHCl 2 249 -CHCl 2 250 -CHCl 2

-CH 2 -CH = CH 2 -CH 2 -CH = CH 2 -CH 2 -CH = CH 2 -CH 2 -CH = CH 2 -CH 2 -CH = CH 2 -CH 2 -CH = CH 2 -CH 2 -CH = CH 2 -C (CH 3) 2 -CHCH-CH-CH 3 -CH 3 -CH 3 -CH 2 -CH 3 -CH 3 -CH 3 -CH 2 -CH 2 CH 3 CH 3 -CH = CH-CH 3 -CH 3 n-C 3 H 7 -C (CH 3) -CH- n-C 3 H 7 -CH 2 -CH 3 -CH 2 -CH = CH 2 -CH 2 -CH = CH 2 -CH 2 -CH = CH 2 -CH 2 -CH = CH 2 CH 2 -CH 3 —N = C (CH 3) 2 —CH 2 —CH = CH 2 —CH 2 —CH 2 CH 2 —CH 2 —CH 2 —CH 2 —CH = CH 2 sec — C 4 H 9 —C 2 H 5 —C 4 H 9 —C 2 H 5 sec-CsHn -C2H5-C3H7-C2H5

196241

Compound No. R "'-' Ri- - -................ ..... Rz- 251 252 253 254 255 256 257 258 259 260261262 263 264 265 266 267 CHCl 2 CHCl 2 CHCl 2 CHCl 2 CHCl 2 CHCl 2 CH 3 CH 3 CH 2 CH 3 -C 4 H 9 CH 3 CH 3 CHCl 2 -C 2 H 5 CHCl 2 -C 2 H 5 CHCl 2 -C 2 H 5 CHCl 2 -CHCl 2 -CHCl 2 -CHCl 2 -CHCl 2 -CHCl 2 -CHCl 2 ... λ: -CH 3 - C 2 H 5 n-C 3 H 7 n-C 3 H 7 -CHCl 2 n-C 3 H 7 -CHCl 2 n-C 3 H 7 '-CHCl 2 n-C 3 H 7 -CHG 12 n-C 3 H 7 -CHCl 2 C 2 H 5

C5H11 sec-C8Hn n-C8Hn sec-C11H1-C3H7 -CH (CH3) -CH (CH3) -CH3 '

269 —CHCl2 sec-C4H9 n-C &amp; Hi3 t-CUHg — CH (CH3) —CH (CH3) —CH3

ch3 270 —CHCl2

271 -CHGIa

'' 3

C, K 272 —CHCI? 273 —CHCI? O-ch (ch3) of 196241

R

Ri R2

Compound No. 274 275 276 277 ... 278 279 280 281 282 283 284 285 —CHCl 2 —CHCl 2 —CHCl 2 —CHCl 2 —CHCl 2 —CHCl 2 —CHCl 2 CHCl 2 —CHCl 2 —CHCl 2 —CHCl 2 —CHCl 2

CH3 ^ 3

ch3

ch3 1 9 6 241f

287 —CHCl2 in 7 ch3 ..... o

288 ^ -CHCl2 H · -. —CH2 — CH2 —N (C2H5) CHCl2 289 —CHC1 · CH2CH5 —CH2 — CH2 —N (C2H5) CHCb0 290 —CHC12— —C3H6 — NH — C — CHCl2 || -CH 3 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH = CH 2 - (E) 293 —CHCl 2 —C 2 H 5 —EE 294 —CHCl 2 n -C 8 H 5 295 -CHCl 2 11-C 3 H 7 296 -CHCl 2 n-C 8 H 7 297 -CHCl 2. . n-C3Hz Ό 298 -CHCl 2 11-C 3 H 7 11-C 6 H 13 299 -CHCl 2 -C 2 H 4 O-CH 2 -C 2 H 4 -O-CH 3 300 -CHCl 2 -C 2 H 4 O-C 2 H 5 -C 2 H 4 O-C 2 H 5 CHCH2 11-C3H7 303 -CHCl2 1-C3H7 -CH2O -CHCl2 11-C4H9 -CH2 O

307 -CHCl 2 O 308 309 -CHCl 2 -CH 2 O-CH 3 O 310 -CHCl 2 -CH 2 H 3 -CH 2 CH 3 -NH 3 -H 3 312 -CH 2 CH 3 -C 3 H 7 313 -CHCl 3 -CH 2 314 -CHCl 2 -k 4 C 9 9; -CH 315 -CH 2 CH 3 -CH 2 -CH 2 OH 316 -CH 3 -CH 3 -CH 2 -GH 2 —C = N 317 —CH 2 CD 318 —CHCl 11-C 6 H 13 n-C 6 H 13 319 —CHCl 2 · · · · · CH 3 - CH 2 CH 2 CH 3 OCH 2 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 SH 322 CH 2 CH 2 -C (C 2 H 5) 2 C = N 323 CH 2 Cl H -C (G 2 H 5) 2 CsN 324 -CHCl 2 325 - CHCh

1 9 B 2 4 1

Compound No. R 1 R 1 326 -CHCl 2 H 327 —CH 2 Cl 2 328 —CHCl 2 · H 329 —CHCl 2 330 —CHCl 2 · H 331 —CHCl 2 z · H 332 - CHCl 2 H 333 —CH 2 Cl H 334 —CHCl 2… ...... H 335 -CHCl 2 336 -CH 2 Cl 2 ·. -ch3 337 ··. CH 3 Cl 2 -CH 3 O 2 -CHCl 2 H 339 -CHCl 2 -H 340 -CHCl 2 ... H 341 -CHCl 2 FH 342 -CH = CH-CH 2 -CH 2 -CH = CH 2 343, -CHCl 2 H 344 -CHCl 2 H 345 -CHCl 2 H

Rz

-CH2-C (CH3) = CH2-CH2-C (CH3) -CH2-CH2-CH2-O-CH3-CH2-CH2-;

-CH 2 -G = CH-CH 2 -CH 2 CH 2 -CH 2 -CH 2 -CH 2 - (N (C 2 H 5) 2 -CH 2 -CH (OCH 5) 2 O 11 · -CH 2 -CH 2 -NHC — CHCl 2 - CH 2 - GH = CH 2 -CH (NH-C-CHCl 3)

CHCNH-C-CHCL NO, O

—CH (CH = CH2) —NH — C — CHCl2 19B241

Compound No.

Ri

Rz 346 -CHCl2-CH (NH-C-ClCHl) ~ f ~ \ t

O 11 - C Η (N H- C - C H &amp; C l) NO, 348,349

35Q 351 -CHCI2 <$>

H

H

H

H

O

II

Cl -CH (NH-C- CHCl3)

Cl 352

353 'C-NiCNgC ^ Cfys, oo

C-NH-CCH2 -CZN // C-AZH-CfCWaJL-C5Ni | <3 *

O

-C (CH 3) 2 - CsN

-C (CH 3) 2 —C = CH

-C (CH 3) 2 -C = N -CH 2 -CH = CH 2 -CH 2 -CH = CH 2

rG (CH3) 2 — C = N 354 355 356 357 358 359 360 -CH (O-C-CHJ-Z- ^

CH 2 (CH 2 O-CH 3) - (y) (CN 8 -CM-CNZ) -

XXL

NH-C (CN 3) 2 C-CH 3

J 1 -C 0 2 -CH = CH 2

H

H -CH 2 -CH = CH 2 -CH 2 -CH = CH 2 -CH 2 -CH = CH 2

-CfCH3) 2-C = CH

-C (CH 3) 2 -C 8 N -CH 2 -CH = CH 2 -CH 2 -CH = CH 2 CH 3 CH-CH 2 -W-C 1-6;

-CH 2 -CH = CH 2 -CH 2 -CH = CH 2 -CH 2 -CH 2 -CH 2 -NH-Cl.

-C (CH 3) 2 —C = CH 19 0 241

Compound No. R Ri. 361 -CH 2 -CH = CH 2 362 H 393 0 II -CH 2 -CH 2 -C-O-CH 3 H 364 -CHCH 2 H 365; CH, CH 2 CH = CH 2 366 7/0 -CHCl 2 H 367 -CHCl 2 368 -CHCl 2 O-C-CHS 369 -CHCl 2 -CHO 370 -H 371 -CH-CH-CH 3 H 372 -O- 0 H .373 CH3 374 - &amp; FH 375 H 376 —CH2 — C (CH3) 3 H c R2 —CH2 — CH = CH2

- C (CH 2) 2 - C = CH

- C (CH 3) 2 -C 5 CH - C (CH 3) = CH - C 8 N - CH 2 - CH = CH 2

ch3 —CH2 — CH [CH3] 2 —CH2 — CH (§H3) 2 —C (CH3) 3,

I-C (CH 3) 3

—C (CH 3) a — e = CH

- CH (CH 2) - CsCH

-C (CH3) 2-CsN-C (CH3) 2-c = n-C (CH3) 2-CsN ·

Compound No.; R 196241; R 1 R 2 377 378 379 380. 381 382 383 -CH 2 CH 2 - θ

H — C (CH 3) 2 —C = CH

H-C (CH3) 2-CsCH

H-C (CH3) 2-CsCH

H - C (CH 3) 2 - C = N

—CH 3 —CH (CH 3) —C e = CH

H — C (CH 3) 2 —C = CH

H-C (CH3) 2-C = N

384 H

O · 385 —CM2 — O — C — CCl = CCl — ClCl = CCl 2 386 - CHCl 2 ·. . - · '/' 'i- \ t 387. '-RCH2CI 388 - CCl3

-CH 2 -CH = CH 2 -CH 2 -CH = CH 2 Π

Clp H -CH3-NH-C-C ^ -O

O II · H — CHa — NH — C — CHCl3

196 2 ^ 41 R 'Ri Rz

Compound 389 390 391 392 393 394 395 396 397 398

Z 399./ ...... \ _____. 400 401 402 403 404 405 -CHCl 2 -CHCl 2 -CHCl 2 -CHCl 2 -CHCl 2 CH 3 -CHCl 2 -CHCl 2 -CH 2 -O-C (CHCl 2) 2 -OHCH 2 -O-C (CHCl 2) (CCl 3) -

—OH

—GH 2 Cl £ 1

0

C (C-O-CH 3) = C (CH 3) -OH-CH 2 Cl-CH 2 Cl-CH 2 -CH = CH 2 -CH 2 -CH = CH 2 'n-C 6 H 5

H-CH3n-CeHn

OH //

O ii O-C-NH-C 10 O-C-NH-CHA-CWeCW 4

0 -C — O — C2H5 o · '- ·

-C-O-C2H4Cl-C (CF3) 2-OH

0 NH-C-CHCl 2

O

NH 1 - CH 2 CH 2 -CH = CH 2 -CH 2 -CH = CH 2

CH = CH-C-C (CHLi 3 * // 0)

CH 2 CH 2 CH 2 CH 2 -C 6 CH 2 CH 2

Cl

CL — CH 2 —CH 2 —c = nn-C 6 H 13

Compound No. s. R

Rz rrtfzri

Ri 406: —chance — C2H5 407 —CH2Cl n-CsHz 408 —CH2C1 — C3H7 409 —CH2Cl —CH3 410 —CH2Cl —CH3 411 —CH2Cl — C2H5 412 — CH2Cl1-C3H7

413

-CH 2 Cl 414 -CH 2 Cl

CfHs 415

-CH 2 Cl 416 -CH 2 Cl-CH 3 -CH 3 CH 7 417 -CH 2 Cl-CH 3 -CH (CH 3) -CH (CH 3) -CH 3 418 -CH 2 Cl-C 2 H 5 O "0" 3,419 -CH 2 Cl n-C 3 H 7 1-C 4 H 9 420 · -CH 2 Cl n-C 3 H 7 sec-C H H n 421 CH 2 Cl n-C 3 H 7 t-C 4 H 9 422 -CHCl 2 -C 4 H 9 sec-C 4 H 9 423 -CH 2 Cl-C 2 H 5 sec-C 4 H 9 424 -CH 2 Cl 4 -C 4 H 9 -C 3 H 7 425 -CH 2 Cl n-C 4 H 9 -C3H7 426 -CH2Cl n-C4H9-C4H9 427 -CH2Cl ... -CH2-CH2-O- -CH3 -CH2-CH2-O-CH3 428 -CH2Cl-CH2-CH2-O- C2H5-CH2-CH2 —0 — C2H5 429 —CHCl 2 -n-C 3 H 7 · 430 —CH 2 Cl 3 —nC $ H7

431 —CH2 Cl n-C3 H7 CH,

Cl

Cl 41

Compound No. R. Ri R2 · 3

440 441 —CHCh -CHCizy-

cwe 442 -CHCl 2 -C 2 H 5 'ch 4 443 -CHCl 2 -C 2 H 444 -CH 2 O 2 -CH 3 n-C 4 H 8. 445 -CH 2 Cl 2 · · CH 3 n-C 1 H 8. '446 —CHC1. -CHS sec-CiHg 447. -CH 2 Cl-CH 3 sec-C 1 Hg 448 -CH 2 CH-CH 3 n-CsHr 449 -CH 2 Cl-CH 3 n-C 3 H 7 450 -CH 2 · -. n-C 4 H 9 t-C 4 H 19 451-CH 2 Cl 2 -COH 7 sec-C 6 H 45 452 -CH 2 Cl 1 -C 3 H 7 sec-C 8 H 8 453 -CHCl 3; Δ-G 3 H 7 n-CsHn 454 -CH 2 Cl 3 -C 3 H 7 n-CsHn 455 -CH 2 CH 3 -C 7 H 7 -sC 8 H 11

R Ri, R2 19B241

Compound No. 456 457 458 459 460 461 462 463 484 '465 466 467 468 469 470 471 472 473 474 475 —CHCk —CHC12 —CHCk —CHCk —CHCk -CHCk

H

H

... H

H

H

-CH 2 -O-CH 3

O

-CHCk H C (CH 3) = CH-C-O-C 2 H 50 -CHCl 3. '11' —NH — C — CHC - CHCk — CHO — CHC - CH 2 —CH (CH 3) 2 II: —C — CHCk — CHC · H - (CH 2) 3 —O — CH [CH 3] 2 Cl — CHCk H -CHCk. H — C (C H 5) (CH 3) 2 —CHC 3 H — CH 2 Cl ·. —H — C (C 2 H 5) (CH 3) 2 —CH 2 Cl H — C 2 H 4 —O — CH 3 —CH 2 Cl H —CH 2 —CH (OCH 3) 2 -CH = chhQ> H — C (GH3) 2 —c = n .0 H — C (CH3) 2 —CsCH2O1r —CHC12 —CH2CH2 — O — C— · —CH2 — CH2 — O — C — N ( CH 3) 2 —N (CH 3) 2

Compound No. R

Ri R2 198241 476 477 478 479 480 481 482 —CHCl 2 —CHCl 2 —CHCl 2 —CHCl 2 —CHCl 2 —CH 2 Cl — CH 2 Cl 2 CH 2 O · CH 2 CH 2 —O — C — CH 2 —CH 2 —O — C — NH — C 2 H 5 —NH — C 2 H 5

-O-CH 2 CH 2 -O-C-CH 2 -CH 2 -O-C-NH-CH 2 · -NH-CH 2 -CH 1 = CH 2 -CH = GH 2

O-GH2CH2-O-C-NH-I-C3H7

O — CH 2 CH 2 —O — C — NH — C 4 H 9

O II · -CH 2 CH 2 —O-c — NH — CH 3

O-CH 2 -CH 2 -O-C-NH-i-C 3 H 7

O

. II — CH 2 —CH 2 —O — C — NH — C 4 H 9

O

-CH 2 -CH 2 -O-C-NH-CH 3 -CH 2 CH 2 -O-C-CH 2 -CH 2 -O-C — NH — CH 2 · - —S'NH — CH 2 —CH = -CH = CH 2 = CH 2

O

-CH-CH 2 O-C-NH

O

- C 1 -C 4 O-C-NH

O

483

-CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -OH-CH 2 -CH 2 -OH 486 -CHCl 2 -H-CH 2 -CH (OH) (CH 3) 487 -CHCl 2 H - (CH 2) 3 -OH 488 -CHCl 2 -CH 2 -CH (OH) (CH 3 r -CH 2 -CH (OH) (CH 3) 489 -CHCl 2 X · 3 ch 3 ch 3 490 —CH 2 OH — C 2 H 5 —C 2 H 5 491 -CH 3 O -sc »-0 492 H - CH 2 --CH (CH 3) 2 493 —CH 2 —SO 2 —O — CH 3 —C 2 H 5 —C 2 H 5 494 —C 3 H 5 Br — —SO 2 · 495 —CHCl 2 496 —CCl 3

23 196241 24

Compound No. R

R 1 R 2 497 — CCb 498 — CCb

499-CH2Cl 500. —C.Cls — CH3 501 —CH2Cl H 502 —CCH1 H 503 —CHCl2 H 504 —CHC12 — C2H5 505 —CiCl2 —Ci3i7 506 —CHC12 n-C4H9 507 —CCl3 — C2H5 508 —CCI3i-C3H7 509 —CiCl3 -C4H9 510 TtCHCl2 H

—CH3; - C 1 H 3 Br-C 2 H 4 Br-C 1 H 6 Br-n-C 4 H 9 i-C 3 H 7 -halo-C 4 H 4 -C 3 H 3 -C 7 H 7 -C 4 H 9

5X1-CCb H512 -CH2ClH513 -CHCl2H

—C (H 1 H 3) (C 2 H 5) —C n N — G (CH 3) (C 2 H 5) —C 5 N — C (CH 3) [C 3 H 5] —CN N

The compositions of the invention are tested as follows.

Testi

Application to soil

Small flat dishes are filled with 10 liters of soil (Felton) and the herbicide and antidote (arithidot) are applied to the soil with stirring in a concrete mixer of about 20 liters, either separately or in combination. If the herbicide and the antidote are separately prepared, the following stock solution is prepared for each compound: The stock solutions of the herbicide are diluted with 100 ml of water and 700 mg of the technical material is diluted with 100 ml of acetone in the case of an antidote. 1.1 kg per hectare (1 pound / acre) when the treated soil is filled into plates of 20X30X7.5 cm.After soil treatment with the herbicide and the antidote in the desired amount, the soil is transferred from the mixer back to the home about 20 liters of seed, which is now ready for sowing, about 0.5 liters of soil is removed from each tray and used to cover the seed. 1.25 centimeters deep into the soil, with sufficient quantities of seeds to be sown in order to achieve good growth status for each piece, and the seed backs to be covered with soil collected from the foreground.

The dishes are then placed in a greenhouse at a temperature of about 21 to 32 ° C and sprayed to a suitable plant growth rate until evaluation. After 3 to 6 weeks the grain tolerance of the proherbicide is determined. The results are presented in Table II below:

Table II

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Small flat dishes are filled with clay-soil (Felton) to which soil herbicides are applied. The soil from each mill is transferred to a concrete mixer of about 20 liters, and the herbicide is added to the soil in the form of a stock solution of 100 ml of water. Agitation is applied with a graduated pipette of the same number of milliliters of stock solution as the herbicide consumption demanded, expressed in pounds per acre. One milliliter of the stock solution contains 7 mg of herbicide, corresponding to 1 pound / acre (or 1.1 kg / h, when applied to the soil in 30X30X7.5 cm dishes). then the soil is returned to the pans, ready for sowing with the soil-treated herbicide and the non-fetish soil, and about 0.5 liter of soil is used to be seeded each time before sowing. if the seed is sown, the depths of 1.25 cm deep are scored and then alternately sown with the treated and untreated shrubs, with 6 or more seeds each in each scratch. The seed is treated by shaking 50 mg of the active ingredient together with 10 g of seed in a suitable container until the seed is uniformly covered by the active agent. In some instances, powdered or solid active compounds in acetone are dissolved to more efficiently apply the active ingredient to the seed.

After sowing, the seeds are covered with soil before sowing and the plates are placed in a glass at a temperature of about 21-32 ° C. To ensure good plant growth conditions, the sprinklers are irrigated. Per 2-4 weeks post-treatment, the percentage damage to the plants was evaluated. In each test, the herbicide alone, the herbicide comhination with the seed protection agent, is applied, and the seed protection agent alone is used to control phytotoxicity. The test results obtained are shown in the following Table III: 196241

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EPTC 6.66 239 0.55 maize 50 ST, MF 80 MF

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EPTC 6.66 272 0.55 maize 0 40 MF

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EPTC 6.66 404 0.55 maize 70 MF 80 MF

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EPTC. 6.66 437 0.55 'maize 50 ST, MF 75 MF

EPTC 6.66 438 0.55 maize 70 ST, MF 80 MF

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EPTC 6.66 470 0.55 maize 60 MF 75 MF

EPTC · 6.66 471 0.55 maize 50 ST, MF 65 MF

EPTC 6.66 472 0.55 maize 20 ST, MF 25 MF

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Claims (8)

196241 27 28 SUBJECT A herbicidal composition based on S-ethyl-dipropylthiocarbamate, S-ethyl-diisobutylthioilcarbamate, S-transdipropylthiolcarbamate, S-2,3,3-trichlorallyl-diisopropylthiolcarbamate, S-ethyl-cyclohexylethylthiocarbamate, 2-chloro-2'-diethyl -N- (methoxymethyl) acetanilide, S-ethylhexahydro-1H-azepine-1-carbothioate, 2-chloro-N-isopropylacetanilide, N, N-dially> 2-chloroacetamide, S-α-chlorobenzyl diethylthiolcarbamate, 2- chloro-4-ethylamino-6-isopropylamino-5-triazine, 2-chloro-4,6-bis (ethylamino) -s-triazine, 2- (4-chloro-6-ethylamino-s-triazin-2-yl) amino-2-methylpropionitrile, 2-chloro-4-cyclopropylamino-6-isocsulfate compound of formula (I) 2,4-D or mixtures thereof, characterized in that it contains a compound of formula (I) as an antidote. R 1 in which R is a C 1 -C 20 haloalkyl group, a haloalkenyl group of 2 to 20, preferably 2 to 12 carbon atoms, an alkylow group with 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, preferably 2 to 12 carbon atoms, cycloalkyl having not more than 20 carbon atoms, cycloalkylalkyl group in which both the cycloalkyl and alkyl moieties contain at most 20 carbon atoms , a halogen atom, a hydrogen atom, an alkoxycarbonyl group in which the alkoxy moiety contains 1 to 20 carbon atoms, the N-alkenylcarbamoyl moiety, the alkenyl moiety containing 2 to 20, preferably 2, up to 12 carbon atoms and the alkyl moiety contains from 1 to 20 carbon atoms, the N-alkenylcarbamoyl group in which the alkenyl moiety contains from 2 to 20, preferably from 2 to 12, carbon atoms, N-alkyl-N- the alkynylcarbamoyl group in which the alkyl moiety contains 1 to 20 carbon atoms and the alkynyl moiety is 2 to 20, preferably 2 to 12 carbon atoms, the N-alkyl-N-alkenylcarbamoylalkyl group in which each alkyl moiety is it always contains 1 to 20 carbon atoms and an alkynyl moiety is 2 to 20 carbon atoms, preferably 2 to 12 carbon atoms, the N-alkenylcarbamoylalkoxyalkyl group wherein the alkenyl moiety contains 2 to 20, preferably 2 to 12 carbon atoms, and the alkoxy and alkyl moieties each contain 1 to 20 carbon atoms, N-alkyl-N the alkynylcarbamoylalkoxyalkyl group wherein each alkyl and alkoxy moiety each has 1 to 20 carbon atoms and the alkynyl moiety contains 2 to 20, preferably 2 to 12 carbon atoms, alkynyloxy having 2 to 20, preferably 2 to 12 carbon atoms, haloalkoxy with 1 up to 20 carbon atoms, a thiocyanatoalkyl group having from 1 to 20 carbon atoms in the alkyl moiety, an alkenylaminoalkyl group in which the alkenyl moiety contains from 2 to 20, preferably from 2 to 12 carbon atoms, and the alkyl moiety contains from 1 to 20 carbon atoms; 20 carbon atoms, alkylcarbonylalkyl groups in which each alkyl moiety contains from 1 to 20 carbon atoms, cyanoalkyl from 1 to 20 carbon atoms in the alkyl moiety, cyanoalkyl; C 1 -C 20 alkyl, alkenylaminosulfonoalkyl wherein the alkenyl moiety contains from 2 to 20, preferably from 2 to 12, carbon atoms and the alkyl moiety contains from 1 to 20 carbon atoms an alkylthioalkyl group in which each of the alkyl moieties contains from 1 to 20 carbon atoms, a haloalkylcarbonyl-oxyalkyl group in which each of the alkyl moieties contains from 1 to 20 carbon atoms each, the alkoxycarbonylalkyl group in which the alkyl moiety contains C 1 -C 20, haloalkenylcarbonyloxyalkyl wherein the alkenyl moiety contains 2 to 20, preferably 2 to 12, carbon atoms and the alkyl moiety contains 1 to 20 carbon atoms, hydroxyhaloalkoxy-alkyl. a group in which both the alkoxy and alkyl moieties each contain from 1 to 20 carbon atoms, the hydroxyalkylcarbonylalkoxyalkyl group in which each of the alkyl moieties contains from 1 to 20 carbon atoms, and the alkoxy moiety contains from 1 to 20 carbon atoms, hydroxy-alkyl of from 1 to 20 carbon atoms , alkoxy-sulfoalkyl group in which both alkoxy and alkyl groups each contain from 1 to 20 carbon atoms, furyl, thiene / yl, alkyldithienyl groups in which the alkyl moiety contains from 1 to 20 carbon atoms, thienylalkyl from 1 to 20 carbon atoms in the alkyl moiety, the phenyl moiety is a substituted phenyl moiety wherein the substituents are selected from the group consisting of halogen atoms, C 1 -C 20 alkyl moieties, C 1 -C 20 haloalkyl moieties, 1 to 20 alkoxy moieties, carbon atoms, carbamoyl groups, nitro groups, carboxylic acid residues and their salts, and halo-genalkylcarbamoyl in which the alkyl moiety contains from 1 to 20 carbon atoms, the phenyl-alkyl group having from 1 to 20 carbon atoms, the phenyl-alkyl group having from 1 to 20 carbon atoms in the alkyl moiety, the phenylalkenyl group containing in the alkenyl moiety 2 to 20, preferably 2 to 12 carbon atoms, substituted phenyl alkenyl having 2 to 20, preferably 2 to 12 carbon atoms in the alkenyl moiety, wherein the substituents are selected from the group consisting of a - 198241 29 halogens alkyl groups having 1 to 20 carbon atoms and alkoxy groups having 1 to 20 carbon atoms, halo-phenoxy, phenyl-alkoxy having 1 to 20 carbon atoms in the alkoxy moiety, phenylalkylcarboxyalkyl in which each alkyl moiety contains always 1 to 20 carbon atoms, phenylcycloalkyl having not more than 20 carbon atoms in the cycloalkyl moiety, halegenphenylalkenyloxy having 2 to 20, and preferably 2 to 12, carbon atoms in the alkenyl moiety; a (C1-C20) -alkyl-phenylalkyl-phenylalkyl group, (C1-C20) -alpha-halobenzyalkyl, -bicycloalkyl-(C20-C) -alkyl group, alkenylcarbamoyl-piperidinyl-containing group in an alkenyl moiety of 2 to 20, preferably 2 to 12 carbon atoms, an alkynylcarbamoylpyridinyl group containing valkynyl moieties of 2 to 20, preferably 2 to 12 carbon atoms, a dialkenylcarbamoylbicycloalkynyl group containing in each alkenyl moiety 2 to 20, preferably In each cycloalkenyl moiety having at most 20 carbon atoms, in each case 2 to 20 carbon atoms, preferably 2 to 12 carbon atoms, and at most 20 carbon atoms in each cycloalkenyl moiety, all of which may be carboxylated in each cycloalkenyl moiety; have a straight or branched chain, and each of R 1 and R 2, which may be the same or different, represents an alkenyl group having 2 to 20, preferably 2 to 12 carbon atoms, a haloalkenyl group having 2 to 20, preferably 2 to 12 carbon atoms, a hydrogen atom, alkyl having 1 to 20 carbon atoms, haloalkyl having 1 to 20 carbon atoms, alkynyl group having 2 to 20, preferably 2 to 12 carbon atoms, cyanoalkyl group having 1 to 20 carbon atoms in the alkyl moiety, hydroxyalkyl group having 1 to 20 carbon atoms in the alkyl moiety; 20 carbon atoms, hydroxyhaloalkyl of 1 to 20 carbon atoms, haloalkylcarboxyalkyl having, in each alkyl moiety, 1 to 20 carbon atoms, alkylcarboxy-alkyl containing in each alkyl moiety 1 to 20 carbon atoms, alkoxy carboxyalkyl having both valkoxy and alkyl moieties of 1 to 20 carbon atoms, thioalkylcarboxyalkyl containing 1 to 1 carbon moiety in each alkyl moiety; 20 carbon atoms, alkoxycarbonyl-alkyl having in each case 1 to 20 carbon atoms in the alkoxy and alkyl moieties, alkylcarbamoyloxyalkyl groups containing in each case 1 to 20 carbon atoms; alkyl of 1 to 20 carbon atoms, an amino group, a formyl group, a halo-alkyl-N-alkylamido group having in each alkyl moiety 1 to 20 carbon atoms, a haloalkylamido group containing in the alkyl moiety 1 to 20 carbon atoms, haloalkylamidoalkyl having from 1 to 20 carbon atoms in each alkyl moiety, haloalkyl-N-alkylamido-alkyl having from 1 to 20 carbon atoms in each alkyl moiety, haloalkylamidoalkenyl moiety C 1 -C 20 alkyl and C 2 -C 20 alkenyl, preferably C 2 to C 12 alkyl, C 1 -C 20 alkylimino, C 20 cycloalkyl, C 1 -C 5 alkylcycloalkyl in an alkyl moiety of 1 to 20 carbon atoms and in a cycloalkyl moiety no more than 20 carbon atoms, an alkoxyalkyl moiety containing alkoxy and alkyl in each case 1 to 20 carbon atoms, alkylsulfonyloxyalkyl having 1 to 20 carbon atoms in each alkyl moiety, mercaptoalkyl groups having 1 to 20 carbon atoms, alkylaminoalkyl groups containing 1 to 20 carbon atoms in each alkyl moiety , an alkoxycarbonylalkenyl group having from 1 to 20 carbon atoms in the alkoxy moiety and from 2 to 20, preferably from 2 to 12 carbon atoms, a haloalkylcarbonyl group having from 1 to 20 carbon atoms in the alkyl moiety, an alkylcarbonyl group having 1 to 20 carbon atoms, up to 20 carbon atoms in the alkyl, alkenylcarbamoyloxy-alkyl containing in the alkenyl moiety 2 to 20, preferably 2 to 12 carbon atoms, and in the alkyl moiety 1 to 20 carbon atoms, cycloalkylcarbamoyloxyalkyl containing no more than 20 in the cycloalkyl moiety carbon atoms and in the alkyl moiety 1 to. Carbon atoms, C 1 -C 20 alkoxycarbonyl alkoxy, C 1 -C 20 haloalkoxycarbonyl, C 1 -C 20 halo-phenylcarbamoyl-oxyalkyl, cycloalkenyl 20 carbon atoms, phenyl groups, substituted phenyl groups, substituents are selected from the group consisting of alkyl groups having from 1 to 20 carbon atoms, halogen atoms, haloalkyl groups having from 1 to 20 carbon atoms, alkoxy groups from 1 to 20 carbon atoms, haloalkylamido-C 1 -C 20 -alkyl, phthalamido, hydroxy, C 1 -C 20 -alkylcarbamoyloxy, alkenylcarbamoyl-C 2 -C 20 alkenylcarbonyloxy groups Carbon, (C 1 -C 20) -alkyl-alkylamido, (C 1 -C 20) haloalkylamido-C an alkyl moiety of an alkylcarbonyl group having from 1 to 20 carbon atoms and a valenyl group having from 2 to 20, preferably from 2 to 12 carbon atoms, a phenylsulfonyl group, a phenylalkyl group having from 1 to 20 carbon atoms in the alkyl moiety, substituted by a phenylalkyl group C 1 -C 20 alkyl, wherein the substituents are selected from halogen atoms, C 1 -C 20 alkyl groups, di-oxyalkylene groups having 1 to 20 carbon atoms, 196241 31 k in the alkylene moiety a halophenoxyalkyl-amidoalkyl group having from 1 to 20 carbon atoms in each alkyl group, an alkylthiodiazolyl group having from 1 to 20 carbon atoms in the alkyl moiety, a piperidyl alkyl group having from 1 to 20 carbon atoms in the alkyl moiety, a thiazolyl group , alkylthiazolyl having 1 to 20 carbon atoms, alkylthiazolyl, halobenzothiazolyl, furyl- C 1 -C 20 alkyl, pyridyl, C 1 -C 20 alkyl pyridyl, C 1 -C 20 alkyl alkoxyl, C 1 -C 20 alkylthiohydrofuryl alkyl an alkyl moiety, a 3-cyano-, 4,5-polyalkylene-thienyl group having from 1 to 20 carbon atoms in each alkylene moiety, and a haloalkylacetamidophenyl alkyl moiety containing from 1 to 20 carbon atoms in each alkyl moiety, an ε-α-balogenalkyl acetyl donitrophenylalkyl moiety containing in each alkyl moiety 1 to 20 carbon atoms in each alkyl moiety, 1 to 20 carbon atoms in each alkyl moiety or a cyanoalkenyl moiety containing 2 to 20, preferably 2 to 12 carbon atoms in each alkyl moiety; or R1 and Ra together may form piperidinyl. a radical, an alkylpiperldinyl radical having from 1 to 20 carbon atoms in the alkyl moiety, an alkyl radicals of 1 to 20 carbon atoms in the alkyl radical, a morpholyl radical, an alkylmorpholyl radical having from 1 to 20 carbon atoms in the alkyl radical, an azobicyclononyl radical, a benzoalkylpyrrolidinyl radical having from 1 to 20 carbon atoms in the alkyl moiety, oxazolidyl moiety, alkyloxazolidyl moieties having 1 to 20 carbon atoms in the alkyl moiety, perhydroquinolyl moiety or alkylamino-alkenyl moiety containing 1 to 20 carbon atoms in the alkyl moiety and in alkenyl moieties 2 to 20 , preferably from 2 to 12 carbon atoms, all of the abovementioned aliphatic radicals R 1 and R 2 being straight or branched, provided that when R 1 is hydrogen, R 2 is other than hydrogen or halophenyl. 2. A composition according to claim 1, wherein the antidote is a compound of formula (I) wherein R is hydrogen, halogen, C1 -C20 alkyl, haloalkyl C 1 -C 20 -alkyl, C 2 -C 20 -cycloalkyl, C 2 -C 20 -cycloalkyl-alkyl, C 2 -C 20 -alkyl, C 2 -C 12 -alkenyl, halo-alkenyl C 2 -C 20 haloalkoxy, C 2 -C 20 haloalkoxy, C 2 -C 20 alkynyloxy, C 1 -C 20 hydroxyalkyl groups , an alkylthioalkyl group in which each of the alkyl moieties contains 1 to 20 carbon atoms or a hydroxyhaloalkoxyalkyl group in both the alkoxy and alkyl moieties. each part contains from 1 to 20 carbon atoms and each of R 1 and R 2, which may be the same or different, represents a hydrogen atom, a C 1 -C 20 alkyl group, a C 1 -C 20 haloalkyl group, an alkenyl group a group having from 2 to 20, preferably from 2 to 12 carbon atoms, a haloalkenyl group having from 2 to 20, preferably from 2 to 12 carbon atoms, an alkynyl group having from 2 to 20, preferably from 2 to 12 carbon atoms, a hydroxyalkyl group having from 1 to 20 atoms carbon, a hydroxyhaloalkyl group having from 1 to 20 carbon atoms, a cycloalkyl group having at most 20 carbon atoms, an alkylcycloalkyl group wherein the alkyl moiety contains from 1 to 20 carbon atoms and the cycloalkyl moiety is at most 20 carbon atoms, an alkoxyalkyl group wherein the alkoxy and alkyl moieties each contain 1 to 20 carbon atoms or the cycloalkenyl moiety having not more than 20 carbon atoms, provided that when R1 is hydrogen, R2 is other than hydrogen. 3. A composition according to claim 1, wherein the substance is a compound of formula I wherein R is C1 -C20 haloalkyl and R1 and Ra together form a piperidinyl moiety, an alkyl piperidinyl moiety. a radical having from 1 to 20 carbon atoms, an alkyl tetrahydropyridyl radical having from 1 to 20 carbon atoms, a morpholyl radical, an alkylmorpholyl radical containing from 1 to 20 carbon atoms, an azabicyclononyl radical, a benzoalkyl-pyrrolidinyl radical having from 1 to 20 carbon atoms, an oxazolidyl radical, an alkyloxazolidyl radical having from 1 to 20 carbon atoms, a perhydroquinolyl radical or an alkylamino-alkenyl radical wherein the alkyl radical contains from 1 to 20 carbon atoms and an alkenyl radical 2 to 20 carbon atoms, preferably 2 to 12 carbon atoms. 4. A composition as claimed in claim 1, wherein the antiplatelet agent is a compound of formula (I) wherein R is phenyl substituted with a phenyl group, wherein the substituents are selected from the group consisting of carbonyl, haloalkyl groups having from 1 to 20 carbon atoms, alkoxy groups having from 1 to 20 carbon atoms, nitro groups, carboxylic acid radicals and their salts, carbamoyl groups and haloalkylcarbamoyl groups containing from 1 to 20 carbon atoms in the alkyl moiety , a phenylalkyl group wherein the alkyl 19624133 moiety contains from 1 to 20 carbon atoms, a phenylhaloalkyl group having from 1 to 20 carbon atoms in the alkyl moiety, a phenylalkenyl group containing from 2 to 20, preferably from 2 to 12, carbon atoms in the alkenyl moiety , substituted phenylalkenyl containing in the alkenyl moiety 2, 20, preferably 2 and 12 carbon atoms, wherein the substituents are selected from the group consisting of halogen atoms, alkyl groups having from 1 to 20 carbon atoms, and alkoxy groups having from 1 to 20 carbon atoms, halo-phenoxy, phenylalkoxy having from 1 to 20 carbon atoms, phenylalkylcarboxyalkyl containing in each alkyl moiety having 1 to 20 carbon atoms, a phenylcycloalkyl moiety having no more than 20 carbon atoms in the cycloalkyl moiety, a halophenyl-alkenyloxy group containing in the alkenyl moiety 2 to 20, preferably 2 to 12 carbon atoms, a halo-thiophenylalkyl group containing in the alkyl moiety 1 to 20 carbons or halo-phenoxyalkyl containing 1 to 20 carbons in the alkyl moiety and each of R 1 and R 2, which may be the same or different, is a hydrogen atom, an alkyl group having from 1 to 20 carbon atoms, an alkenyl group being 2 to 20, preferably 2 to 12 carbon atoms or alkynyl the carbon group having from 2 to 20, preferably from 2 to 12 carbon atoms, provided that when R 1 is hydrogen, R 2 is other than hydrogen. 5. A composition according to claim 1, wherein the agent is an antidote. a compound of the above general formula (I) in which R represents an N-alkenylcarbamoyl alkyl group in which the alkenyl moiety contains 2 to 20, preferably 2 to 12 carbon atoms and an alkyl moiety of 1 to 20 carbon atoms, an N-alkenylcarbamoyl group containing in the alkenyl moiety 2 to 20, preferably 2 to 12 carbon atoms, the N-alkyl-N-alkynylcarbamoyl group in which the alkyl moiety contains 1 to 20 carbon atoms and the alkynyl moiety contains 2 to 20, preferably 2 to 12 atoms carbon, N-alkenylcarbamoylalkoxyalkyl wherein the alkenyl moiety contains 2 to 20 carbon atoms, preferably 2 to 12 carbon atoms, and the alkoxy and alkyl moieties each contain 1 to 20 carbon atoms, N-alkyl-N-alkynylcarbamoyl a alkoxyalkyl group in which the alkynyl moiety contains 2 to 20, preferably 2 to 12 carbon atoms, each of the alkyl moieties having 1 to 20 carbon atoms and an alkoxy moiety of 1 to 20 carbon atoms, dialkenylcarbamoylbicycloalkalo an enyl group in which each alkenyl moiety each contains 2 to 20, preferably 2 to 12, carbon atoms and each cycloalkenyl moiety has at most 20 carbon atoms or alkynylcarbamoylbicycloalkenyl moiety in which the alkynyl moiety contains 2 to 20 , preferably 2 to 12 carbon atoms and each cycloalkenyl moiety having at most 20 carbon atoms each, and R 1 and R 2, which may be the same or different, represent 34 hydrogen, alkyl of 1 to 20 an carbon atom, an alkenyl group having from 2 to 20, preferably from 2 to 12 carbon atoms, or an alkynyl group having from 2 to 20, preferably from 2 to 12 carbon atoms, with the proviso that when R1 is hydrogen, R2 has a different hydrogen atom. 6. A composition as claimed in claim 1, wherein the antidote is a compound of formula (I), wherein R is C1-C20 haloalkyl or R1 and R2, they may be the same or different, an alkyl group having from 1 to 20 carbon atoms, an alkenyl group having from 2 to 20, preferably from 2 to 12 carbon atoms, a hydrogen atom, an alkoxyalkyl group containing from 1 to 20 carbon atoms in each alkoxy group, a phenyl group substituted by a phenyl group a group wherein the substituents are selected from the group consisting of alkyl groups having from 1 to 20 carbon atoms, halogen atoms, haloalkyl groups having from 1 to 20 carbon atoms, alkoxy groups having from 1 to 20 carbon atoms, haloalkyl amido groups containing from 1 to 20 carbon atoms carbonyl, phthalimido, hydroxy, alkylcarbamoyloxy containing 1-20 at the alkyl moiety carbon, alkenylcarbamoyloxy having 2 to 20, preferably 2 to 12 carbon atoms in the alkenyl moiety, 1 to 20 carbon alkyl amido groups, 1 to 20 carbon halogenoalkyl amido groups and alkylcarbonylalkenyl moieties containing from 1 to 20 carbon atoms in the alkyl moiety and from 2 to 20, preferably from 2 to 12 carbon atoms in the alkyl moiety, a phenylalkyl group containing from 1 to 20 carbon atoms or substituted by a phenylalkyl group containing alkyl. parts of 1 to 20 carbons wherein the substituents are selected from the group consisting of halogen atoms, C 1 -C 20 alkyl groups, C 1 -C 20 dioxyalkylene groups, and halo-phenoxyalkylamidoalkyl groups each containing in each case from 1 to 20 carbon atoms, provided that when R @ 1 is hydrogen, R @ 2 is other than hydrogen. 7. A composition as claimed in claim 1 wherein R is a C1 -C20 haloalkyl group having from 1 to 20 carbon atoms, cyanoalkyl group having from 1 to 20 carbon atoms, and a cyanoalkyl group. C 1 -C 20 -alkyl, C 1 -C 20 -alkyl thiocyanatoalkyl, C 1 -C 20 -alkyl cyanoalkyl, C 20 -cycloalkyl, bicycloalkyl a group containing in each cycloalkyl moiety at most 20 carbon atoms, a halophenyl group, a phenylalkenyl group containing in the alkenyl moiety 2 to 20, preferably 2 to 12 carbon atoms, or a haloethylalkenyl group containing in the alkenyl moiety 2 to 20 carbon atoms; carbon atoms of 2 to 20, preferably 2 to 12 carbon atoms, and each of R 1 and R 2, which may be the same or different, is cyanoalkyl of 1 to 20 carbon atoms in the alkyl moiety, hydrogen, alkenyl of 2 to 20, preferably 2 to 12 carbon atoms, or alkyl of 1 to 20 carbon atoms, provided when R 1 is hydrogen, R 2 is other than hydrogen. 8. A composition as claimed in any one of claims 1 to 7 wherein each weight fraction of the herbicidal active compound comprises 0.0001 to 30 parts by weight of an antidote. 9. A composition according to claim 1, based on S-ethyl dipropylthiocarbamate, S-ethyl diisobutylthiolcarbamate, 36 S-propyl dipropylthiolcarbamate, S-2,3,3-trichlorallyl-diisopropylthiolcarbamate, S-ethylcyclohexylethylthiocarbamate, S- 4-chlorobenzyl-diethylthiolcarbamate or mixtures thereof, characterized in that the counter-acting compound comprises a compound of the above general formula (I) in which R is a haloalkyl group having 1 to 20 carbon atoms or a haloalkenyl group having 2 to 4 carbon atoms. 20, preferably 2 to 12 carbon atoms and each of R 1 and R 2, which may be the same or different, represents a hydrogen atom, an alkyl group having from 1 to 20 carbon atoms, an alkenyl group having from 2 to 20, preferably from 2 to 12 carbon atoms, alkynyl groups having 2 to 20 carbon atoms, preferably 2 to 12 carbon atoms, cyanoalkyl groups having 1 to 20 carbon atoms in the alkyl moiety or phenyl groups. Severografia, n. P., Plant 7, Most