Patent GB-1049344-A (GB)
Title: New fungicidal compositions
IPC: C07D207/22
Filed: 1963-07-09
Abstract: Heterocyclic compounds with one nitrogen atom as ring hetero atom and 4 to 8 carbon atoms as ring members of the formula (II) <FORM:1049344/C2/1> wherein R2 represents an alkyl radical with from 4 to 15 carbon atoms, which may be substituted by halogen atoms or by an alkoxy or an alkylthio group with from 1 to 4 carbon atoms, a monoalkylamino radical with 4 to 12 carbon atoms, the benzylamino radical, an alkoxypolyethyleneoxy-alkyl radical or the group -(CH2)y-NH-R3 wherein R3 represents an alkyl radical with from 1 to 20 carbon atoms, a 0-, m- or p-chloropentene radical or the alkyl substituted azacyclopentene integrer from 1 to 6, and n is an interer from 3 to 13, but only 3, 5 or 7 of the corresponding carbon atoms being ring members, and their salts with organic or inorganic acids and their quaternary salts are made by a process which comprises reacting equivalent amounts of a compound of the general formula (III). wherein R4 represents an alkyl radical having from 1 to 3 carbon atoms, A represents oxygen or sulphur, and of a primary amine of the general formula (V) NH2-R2 wherein R2 is as above defined, and if desired, converting the reaction products so obtained into their salts with organic and inorganic acids or into their quaternary salts.  Particularly useful compounds falling within the above general formula are <FORM:1049344/C2/2> <FORM:1049344/C2/3> <FORM:1049344/C2/4> <FORM:1049344/C2/5> <FORM:1049344/C2/6> <FORM:1049344/C2/70> <FORM:1049344/C2/81> Numerous detailed examples of the preparation of these compounds illustrate the invention, which compounds find utility as fungicides and bactericides (see Divisions A2, A5 and C2).ALSO:Fungicidal compositions, suitable for the treatment of plants or parts thereof as well as for the protection of wood, textiles, furs, leather, paper comprise as the active ingredient at least one heterocyclic compound with one nitrogen atom as ring hetero atom and 4 to 8 carbon atoms as ring members of the general formula I:-  <FORM:1049344/A5-A6/1> wherein R represents an alkyl radical containing from 4 to 20 carbon atoms, which may be substituted by halogen atoms or by an alkoxy or an alkylthio group with from 1 to 4 carbon atoms, an aralkyl radical, a monoalkylamino radical with 4 to 12 carbon atoms, the benzylamino radical, an alkoxypolyethyleneoxy-alkyl radical or the group <FORM:1049344/A5-A6/2> wherein R1 represents an alkyl radical with from 1 to 20 carbon atoms, a o-, m- or p-chlorophenyl radical or the alkyl substituted azacyclopentene-(5)-yl or azacycloheptene-(7)-yl radicals, and m is an integer from 2 to 6, and n is an integer from 3 to 13, but only 3, 5 or 7 of the corresponding carbon atoms being ring members, and/or its salts with inorganic or organic acids and/or its quaternary salts, these active ingredients being combined with suitable solid pulverulent carriers and/or with high boiling hydrocarbons and/or with distributing agents containing capillary active substances (See Division C2).  These compositions may be used as a dry seed dressing having an action on Tilletia tritici, Fusarium culmorum. The compositions may also contain other fungistats and bacteriostats.  Solid pulverulent carriers specified include talcum, kaolin loess, chalk or ground limestone.  Wettable powders may be produced by adding dispersing agents for example sulphite waste liquor.  The active substances can be dissolved in organic solvents, for example trichlorethylene, petroleum fractions, acetone, or higher ketones.  The examples describe the preparation of compositions containing 4-tert.butyl-7-myristylamino-3, 4, 5, 6-tetrahydro-2H-azepine with polyvinyl pyrrolidone and water, suitable for combating fungi especially in orchards, 7-octylamino-3, 4, 5, 6-tetrahydro-2H-azepine, polyvinyl alcohol sulphite waste liquor, chalk, kaolin, a wetting agent based on alkyl and aryl sulphonates and water to yield a wettable powder suitable for use in fruit cultivation, 7-octylhydrazino-3, 4, 5, 6-tetrahydro-2H-azepine, dimethyl formamide, and an alkyl aryl sulphonate to give an emulsifiable solution, 9-dodecylamino-3, 4, 5, 6, 7, 8-hexahydro-2H-azonine, dimethyl sulphoxide, cyclohexanone, an alkylaryl polyethylene oxide to give an emulsifiable solution.  The examples also include comparative tests for the inhibition of germination of the fungi.