Patent GB-1479624-A (GB)
Title: (3-alkoxycarbonyl-2-thioureido)benzene derivatives
IPC: C07C335/28
Filed: 1974-11-05
Abstract: 1479624 Compositions containing thiourea derivatives MAY & BAKER Ltd 4 Nov 1975 [5 Nov 1974] 47889/74 Headings A5B and ASE [Also in Division C2] Anthelmintic and fungicidal compositions contain (I) as active ingredient wherein R<SP>1</SP> represents a straight- or branchedchain alkyl group containing not more than 4 carbon atoms (preferably methyl), R<SP>2</SP> represents a group of the formula [wherein R<SP>3</SP> represents a straight- or branchedchain alkyl group containing not more than 6 carbon atoms, e.g. methyl or ethyl, a cycloalkyl group containing from 3 to 7 carbon atoms, e g. cyclopentyl, a straight- or branched-chain alkenyl or alkynyl group containing from 3 to 6 carbon atoms, e.g. allyl or prop-2-ynyl, an aralkyl, e.g. phenylalkyl, group with 1 or 2 carbon atoms in the alkyl moiety, for example benzyl, or R<SP>3</SP> represents an aryl, e.g. phenyl, group which may optionally be substituted by a halogen (e.g. chlorine) atom or by a straight- or branched-chain alkyl or alkoxy group containing from 1 to 3 carbon atoms, or represents a cycloalkylalkyl group in which the cycloalkyl moiety contains from 3 to 7 carbon atoms and the alkyl moiety contains 1 or 2 carbon atoms, e.g. cyclohexylmethyl, R<SP>4</SP> represents a hydrogen atom or, preferably, a straight- or branched-chain alkyl group containing not more than 4 carbon atoms, e.g. ethyl, T and T<SP>1</SP>, which may be the same or different, each represent an oxygen or sulphur atom of a sulphinyl (-SO-) group and m is an integer from I to 7 inclusive and is preferably 2] whose position on the benzene ring is either para to the group -NHCSNHCOOR<SP>1</SP> or para to the group -NHCOAZ, A represents a bivalent straight chain aliphatic hydrocarbon radical containing not more than 4 carbon atoms which may be saturated or unsaturated (e.g. a methylene, polymethylene e.g. ethylene, or vinylene radical) and which may optionally be substituted by at least one methyl group, and Z represents a group of the general formula:- wherein R<SP>5</SP> represents a hydrogen atom or a straight- or branched-chain alkyl group containing not more than 4 carbon atoms, e.g. methyl or ethyl, R<SP>6</SP> represents a hydrogen atom or a straight- or branched-chain alkyl group containing not more than 4 carbon atoms, e.g. methyl or ethyl or a phenylalkyl group with I or 2 carbon atoms in the alkyl moiety, preferably benzyl, and R<SP>7</SP> represents a hydrogen atom or a straight- or branched-chain alkyl group containing not more than 4 carbon atoms, e.g. methyl or ethyl, or R<SP>6</SP> and R<SP>7</SP> together with the nitrogen atom to which they are attached form a 5-, 6- or 7-membered heterocyclic ring which may contain in the ring one or two further hetero atoms selected from oxygen, nitrogen and sulphur, and which may optionally be substituted by one or more straight- or branched-chain alkyl groups each containing not more than 6 carbon atoms, for example a pyrrolidin-1-yl, piperidino, morpholino, piperazin-1-yl or 4-alkylpiperazin-1-yl, e.g. 4-methylpiperazin-1-yl, group and X<SP>(-)</SP> represents a pharmaceutically acceptable or agriculturally acceptable anion. The anthelmintic compositions are administered orally, parenterally or topically and may optionally contain auxiliary therapeutic agents, for example fluke drugs such as 4-cyano-2-iodo-nitrophenol, hexachloroethane, carbon tetrachloride, 3, 3', 5, 5', 6, 6'-hexachloro-2, 2'-dihydroxydiphenylmethane, 2, 2'-dihydroxy-3, 3', 5, 5', 6-pentachlorodiphenylmethane, 2, 2'-dihydroxy-3, 3,'5, 5', 6-pentachlorobenzanilide, 2, 2'-dihydroxy-3, 3'-dinitro-5, 5'-dichlorodiphenyl, bis[2-(4-acetamidophenoxy)ethyl] ether or 2-acetoxy-4'- chloro-3, 5-diiodobenzanilide, 2-(4-thiazolyl)- benzimidazole, 5(6)-isopropoxycarbonyl-amino- 2-(4-thiazolyl)benzimidazole, methyl 5(6)-butyl- 2-benzimidazolecarbamate, methyl 5(6)-benzoyl- 2-benzimidazolecarbamate, 6-phenyl-2, 3, 5, 6- tetrahydro-imidazo[2, 1-b]thiazole, trans-1, 4, 5, 6 - tetrahydro - 1 - methyl - 2 - (2 - thien - 2'- ylvinyl)pyrimidine, phenothiazine, cyanacethydrazide, piperazine and its salts such as piperazine adipate, 1 - diethylcarbamoyl - 4 - methylpiperazine, tetrachloroethylene, 4, 4'-dichloro-2, 2'-dihydroxydiphenyl-methane, N-(2- choloro - 4 - nitrophenyl) - 5 - chlorosalicylamide, N, N-dibutyl-4-hexyloxynaphthamidine, trans-1, 4-bis(2-isothiocyanatoethyl)cyclohexane and 1-styrylpyridinium salts, e.g. the bromide, embonate, amsonate or isethionate. The fungicidal compositions may also contain when used agriculturally and not pharmaceutically, as well as the compound or compounds of formula I, pesticides such as insecticides, for example γ-1, 2, 3, 4, 5, 6-hexachlorocyclohexane, or other fungicides, for example 3a, 4, 7, 7a-tetrahydro-N-(trichloromethanesulphenyl)phthalimide.