Patent GB-819069-A (GB)
Title: Sulfonyl ethylene fungicides
IPC: C07C317/08
Filed: 1955-12-05
Abstract: The invention comprises bis-(alkylsulphonyl)-ethylenes of the formula RSO2CH=CHSO2R where R is alkyl of 3 to 12 carbon atoms, and a process for making them by reacting the corresponding 1 : 2 - bis - (alkylmercapto)-ethylenes with an oxidizing agent.  Mixtures of cis- and trans-isomers are formed which are separated by the usual methods, and a number of cis- and trans-isomers of compounds of the above formula are specified. Oxidizing agents specified are hydrogen peroxide, potassium permanganate, sodium hypochlorite, chromic oxide and dilute nitric acid and electrolytic oxidation may be used.  The 1 : 2-bis-(alkylmercapto) ethylenes used in the reaction may be made by reacting one mol. of a 1 : 2-dihaloethylene, where the halogen is chlorine or bromine or one of each, with a mercaptan.  In examples: (1) n-propyl mercaptan is reacted with cis-1 : 2-dichloroethylene and the 1 : 2-bis-(n-propylmercapto) ethylene obtained is oxidized with hydrogen peroxide in acetic acid to mixed cis- and trans-1 : 2-bis-(n-propylsulphonyl) ethylene, the isomers being separated by recrystallization; in further examples, the isopropyl, n-butyl, n-amyl, n-octyl and lauryl mercapto ethylenes are similarly oxidized to the corresponding 1 : 2 - bis - (alkylsulphonyl)-ethylenes.ALSO:Seeds are protected against fungi by treatment with a bis (alkylsulphonyl)-ethylene of the formula RSO2 CH = CHSO2R where R is an alkyl group of 3 to 12 carbon atoms. Thus pea seeds are uniformly coated with bis (n-octylsulphonyl) or bis (lauylsulphonyl) ethylene or with a mixture thereof with Homer clay by rolling mixtures of the seed and fungicide in screw-cap bottles on high-speed rollers.ALSO:Fungicidal compositions comprise a bis-(alkylsulphonyl) ethylene of the formula RSO2CH = CHSO2R where R is an alkyl group of 3 to 12 carbon atoms together with a conditioning agent which may be a surface-active or dispersing agent such as a detergent, soap, metal salts of alkyl or alkylaryl sulphonates, alkyl sulphates, alkylamide sulphonates including fatty methyl taurides, alkylamyl polyether alcohols, fatty acid esters of p polyhydric alcohols, the ethylene oxide addition products of such alcohols such as the hexitol product and addition products of long chain mercaptans and ethylene oxide, so that a dispersion is formed on dilution with water.  The conditioning agent may be a water-insoluble solvent such as kerosene, benzene, naphtha, butanol, oleyl alcohol or ethers or esters thereof, perchloroethylene or trichloroethylene, so that an oil-in-water emulsion is formed on mixing with water containing a surface-active agent, or the conditioning agent may comprise the solvent and surface-active agent. The conditioning agent may also comprise a solid inert carrier with or without a surface-active agent to form wettable powders or dusts. Carriers mentioned are soybean flour, tobacco flour, walnut shell flour, wood flour, sulphur, tripolite, diatomite, calcium lime, magnesium lime, calcite, dalomite, gypsum, mica, talc, pyrophyllite, montmorillonite, kaolinite, attapulgite, apatite, pumice, attaclay, kieselguhr, chalk, clay, fuller's earth or "Filtrols" (Registered Trade Mark).  The conditioning agent may also comprise an organic solvent such as benzene, xylene, toluene, acetone, methyl ethyl ketone, cyclohexanone, carbon tetrachloride, trichloro- and perchloroethylene, ethyl, butyl and amyl acetates, ethanol, isopropanol and amyl alcohol, and monoalkyl ethers of diethylene and ethylene glycols.  The compositions may also contain adhesives such as vegetable oils and gums and other pesticidal materials.  In examples: (7) 10 parts of trans-bis-(n-propylsulphonyl)-ethylene, 1 part of the ethylene oxide addition product with hexitol in 1000 parts of water is diluted 1000 times; (8) 100 parts of bis (laurylsulphonyl) ethylene, 1000 parts of pyrophyllite and 0.1 part of sodium keryl sulphonate are mixed and suspended in water.