PL88521B1 - - Google Patents

Description

The subject of the invention is a herbicide containing new carbothiolates as an active ingredient acetidine.

It is known to use S-ethyl-hexahydro-1H-azepine-1-carbothiolane to control plants other than data on crops of crops such as barley, wheat and rice (German Patent No. 1,300,947).

Its performance, however, is unsatisfactory.

It has been found that acetidine carbothiolates of formula I in which R1 is an alkyl group, e.g. wa, ethyl, n is 0-4, X is oxygen or sulfur, have good herbicidal activity.

With the same, and often better, herbicidal action, plants tolerate them better than the known S-ethyl-hexa hydro-1H-azepine-1-carbothiolates.

The active ingredients are obtained by reacting the thiolchloroformic acid ester with optionally substituted acetidine. The same can produce active ingredients if acetidine in the form the corresponding acid N-chloride is reacted with mercaptans. The preparation of acetidine is known from literature.

Example I. Preparation of 2-ethyl- (2,2,4-trimethylacetidine) -1-carbothiolane.

For a mixture of 4.95 parts by weight of 2,2,4-trimethylacetidine and 6 parts of triethylamine in 50 parts by weight of benzene, 6.23 parts of ethyl thionochloroformate are added dropwise at 30-40 ° C. After an hour The triethylamine hydrochloride is not filtered off and the filtrate is washed with water. After drying, it thickens underneath reduced pressure and the residue distilled. 6.70 parts of S-ethyl- (2,2,4-trimethylacetid- no) -1-carbothiolane of structural formula 2 and boiling point: 59 ° C 0-1.

The same method can produce the following compounds: S-methyl- (2,2,4-trimethylacetidine) -1-carbothiolane, boiling point: 70 ° C 0.05 S-propyl- (2,2,4-trimethylacetidine) -1 -carbothiolane, boiling point: 81 ° C 0.052 88 521 Gossypium hirsutum, Leguminosae, e.g. Medicago spp., Trifolium spp., Pisum spp., Phaseolus spp., Arachi s spp., Glycine Max, Chenopodisceae, e.g. Beta vulgaris, Spinacia spp., Solanaceae, e.g. Solanum spp., Nicotiania spp., Capsicum annuum, Linaceae, e.g. Linum spp., Umbeliferae, e.g. Petroselinum spp., Daucus carota, Apium graveolens, Rosaceae, e.g. Fragaria, Cucurbitaceae, e.g. Cucumis spp., Cucurbita spp., Liliaceae, e.g. Allium spp., Vitaceae, e.g. Vitis vinifera, Bromeliaceae, e.g. Ananas sativus.

Example II. In the greenhouse, the test vessels are filled with loamy sandy soil and sown various seeds. The active substances are treated immediately after IV (formula 4), V (formula 5), VI (formula 6) and VII (formula 7) compared with the known active substance III (formula 3), using 1 kg of the substance at a time active per hectare, dispersed or emulsified in 500 l of water per hectare. Sprinkles during the experiment water the plants abundantly. After 4 weeks, it was found that the active substances IV, V, VI and VII were better tolerated by arable crops and better herbicidal activity than the comparative active substance III. Results of dos The services are presented in Table I.

Example III. Various plants with a growth height of 3-15 cm are treated with the active substances IV (formula 4), V (formula 5), VI (formula 6) and VII (formula 7) compared to the known substance III (formula 3) using either per hectare, 1 kg of active substance per hectare, dispersed or emulsified in 500 l of water per hectare.

During the experiment, the plants are watered abundantly. After 4 weeks, it was established that the active substances IV, V, VI and VII show better tolerability by crops with the same herbicidal action from the beginning equivalent to the active substance III.

Claims (1)

Claim 1. A herbicidal agent containing the active substance, a solid or a liquid carrier, characterized in that the active substance is a carbothiolate of the formula I, in which R1 is an alkyl group, n is 0-4, X is an oxygen or sulfur atom and R2 is an aliphatic group optionally substituted one or more times with halogen, hydroxy, alkoxy or cyano. Active substance kg / ha Crop crops Brassica napus (rapeseed) Triticum aestivum (wheat) Undesirable crops Echinochloa crusgalli (chicken millet) Lolium multiflorum (Italian ryegrass) Lolium perenne (English ryegrass) Avena fatua (deaf annual oat) Poa trivialis Table 1 III! 1 10 5 40 20 20 0 I 30 30 IV 1 0 0 95 100 95 60 100 95 V 1 0 0 90 95 90 55 85 85 VI 1 0 0 60 80 80 40 85 85. VII 1 0 0 80 85 90 70 100 95 0 = no harmful 100 = fully harmful 88 521 Active substance kg / ha Crop crops Brassica napus (rape) Triticum aestivum (wheat) Undesirable plants Echinochloa crus galli (chicken millet) Lolium multiflorum (Italian rajgras) ) Lolium perenne (English ryegrass) Avena fatua (deaf oats) Poa annua (annual panicle) Poa trivialis (common panicle) 0 = no harmful 100 = full harmful Table II III 1 10 5 40 20 20 0 30 30 IV 1 0 0 95 95 90 50 95 90 V 1 0 0 90 90 85 45 90 90 VI 1 0 0 60 70 70 40 70 65 VII 1 0 0 90 90 85 50 90 8588 521 (R1) N — CS-R2 X WZdR 1 CH3 CH3 N — CS — CH3 CHq WZCfR U H3CX PH3 N —C — S —C2H5 H CH3 FORMULA 2 CH3 CH3Q N —CS-CH CH, CH, WZdR 5 Qj-CS-C2H6 O WZdR 3 CH3 CH3 Cl ci NCS-CH2— C = CO Cl WZdR 6 CH3 CH3 \ NCS-CH-C2H5 CH3 CH3 WZdR 7 Work. Typographer. UP PRL. Mintage 120 + 18 copies. Price PLN 10