The method of manufacture, method of use and fungicidal active compounds are described herein. The active compounds have the following formula: ##SPC1## Wherein R can be selected from the group consisting of hydrogen, sodium, potassium and ammonium.
CROSS REFERENCE TO RELATED APPLICATION
This application is a continuation-in-part of copending application, Ser. No. 172,205 filed Aug. 16, 1971, now abandoned, entitled Benzimidazole Derivatives As Fungicidal Active Compounds.
2,4-Dioxo-1,2,3,4-tetrahydro-s-triazino-[1,2-a]-benzimidazoles of the formula ##STR1## are produced by reacting a benzimidazole compound of the formula ##STR2## with a diphenyl carbonate of the formula ##STR3## wherein R.sup.1 is optionally substituted alkyl or aryl, alkenyl or dialkylamino, R.sup.2 is hydrogen, alkyl or trifluoromethyl, R.sup.3 is any of the R.sup.1 radicals or hydroxycarbonylalkyl, and R.sup.4 is hydrogen, alkyl or halogen. The reaction can be effected employing the benzimidazole in impure form, without isolation, in the vessel in which it is formed. Those compounds wherein R.sup.1 is a variously .omega.-substituted alkyl radical and R.sup.2 is hydrogen or methyl are new and all the compounds exhibit fungicidal activity.
1-Triorgano-stannyl-3-substituted-2,4-dioxo-1,2,3,4-tetrahydro-s-triazino-[ 1,2-a]-benzimidazoles of the formula ##STR1## in which R.sup.1 is alkyl or cycloalkyl with 4 to 8 carbon atoms, or phenyl, and R.sup.2 is alkyl with 1 to 18 carbon atoms optionally substituted by chlorine, CN, alkoxycarbonyl with 1 to 5 carbon atoms in the alkoxy moiety, alkenoxycarbonyl with up to 5 carbon atoms in the alkenoxy moiety, alkylaminocarbonyl with 1 to 5 carbon atoms in the alkylamino moiety, phenyl, N-morpholino or dialkylamino with 1 to 6 carbon atoms per alkyl group; dialkylamino with 1 to 6 carbon atoms per alkyl group; phenyl or cyclohexyl. R.sup.4 is hydrogen or alkyl with 1 to 4 carbon atoms, which possesses insecticidal, acaricidal and fungicidal properties.
