Patent GB-1031264-A (GB)
Title: Substituted thionocarbamates and their herbicidal use
Inventor: HAM PHILIP CURTIS
IPC: C07C333/02
Filed: 1963-10-24
Abstract: Thionocarbamates of the general formula <FORM:1031264/C2/1> where A represents a halogen substituted alkenyl radical containing less than 5 carbon atoms and R and R1 are separately selected from lower alkyl, lower alkenyl, halogen substituted lower alkenyl, lower alkoxy substituted lower alkyl, lower alkenoxy substituted lower alkyl, phenoxy substituted lower alkyl, cyano-substituted lower alkyl, cyclohexyl or cyclohexenyl, or together with the nitrogen atom to which they are attached constitute a fivemembered, six-membered, or seven-membered heterocyclic nucleus, the term "lower" meaning less than 6C, preferably less than 4C atoms, and especially compounds of the above formula where A is a halogen substituted 2-alkenyl group containing less than five carbon atoms and having all the halogen attached to unsaturated carbon and R and R1 are separately selected from lower alkyl, lower 2-alkenyl, lower alkoxy substituted lower alkyl, lower alkenoxy substituted lower alkyl, cyano substituted lower alkyl, cyclohexyl, cyclohexenyl, monochloroallyl and phenoxy substituted lower alkyl, or together with the nitrogen atom to which they are attached constitute a 4-phenylpiperazinyl, morpholinyl, 2,6-dimethylmorpholinyl, pyrrolidinyl, piperidinyl, 2-methyl-piperidinyl, 5 - ethyl - 2 - methylpiperidinyl, 5ethyl - 3 - methyl - piperidinyl, 2,4,6 - trimethylpiperidinyl or 1 - hexamethyl - lenimine radical are made by reacting a compound of the formula <FORM:1031264/C2/2> with a compound AOH, or by reacting xanthate of the formula A-O-C S S M where M is a hydrogen atom or an alkaline metal atom with monochloracetic acid and reacting the product with an amine of the formula RNHR1.  Particularly preferred compounds are 2-chloroallyl diethylthionocarbamate, 2-chloroallyl dipropylthionocarbamate, 2-chloro allyl dimethylthionocarbamate, 2chloroallyl 1-pyrollidinecarbothionate, 2-chloroallyl N - isopropyl - N - allylthionocarbamate, 2 - chloroallyl - N - 2 - chloroallyl - N -isopropylthionocarbamate, 2 - chloroallyl - N - 2chloroallyl - N - 3 - methoxypropylthionocarbanate, 2 - chloroallyl diallylthioncarbamate, 2 -chloroallyl - 1 - piperidinecarbothionate, 2-chloroallyl-5-ethyl-2-methyl-1-piperidinecarbothionate, 2 - chloroallyl - 5 - ethyl - 3methyl - 1 - piperindine - carbothionate, 2,3dichloro - allyldibutylthionocarbamate, 3,3dichloroallyl - N - cyclohexyl - N - isopropylthionocarbamate, 3,3 - dichloroallyl - N - cyclohexyl - N - ethyl - thionocarbamate.  The Specification describes the preparation of these and other representative compounds which are useful as herbicides.  (See Division A5E).ALSO:Herbicidal compositions comprise a compound of the general formula: <FORM:1031264/A5-A6/1> where A represents a halogen substituted alkenyl radical containing less than 5 carbon atoms and R and R1 are separately selected from lower alkyl, lower alkenyl, halogen substituted lower alkenyl, lower alkoxy substituted lower alkyl, lower alkenoxy substituted lower alkyl, phenoxy substituted lower alkyl, cyano-substituted lower alkyl, cyclohexyl or cyclohenyl, or together with the nitrogen atom to which they are attached constitute a five membered, six membered or seven membered heterocyclic nucleus, the term "lower" having the meaning of less than C6, preferably less than C4, together with an inert diluent, especially in solid inert powder diluent or an aqueous medium containing a wetting or dispersing agent, or a hydrocarbon oil.  The herbicides may be employed by applying to growing vegetation or to soil containing the seeds of such vegetation, a compound of the above formula or a composition containing as active ingredient one of the above compounds. Specified diluents include talc, bentonite, diatomaceous earth, aqueous dispersing agents containing emulsifiers such as alkyl benzene sulphonate, polyalkylene glycol, salts of sulphonated alcohols or sorbitan fatty acid esters.