# US 4,396,617 A · 2-Arylamino-hexahydropyrimidines, compositions containing same, and method of use thereof > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,396,617 A - Document ID: US4396617A - Status: Granted - Kind: A - Application number: 06/264,461 - Filed: 1981-05-18 - Granted: 1983-08-02 - Earliest claimed: 1977-10-18 - Assignees: Duphar International B.V. - Inventors: Hendrik Dolman; Johannes Kuipers - Web page: https://patentgrep.com/patent/US4396617A ## CPC - C07D 239/14: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to said nitrogen atoms - A01N 43/50: 1,3-Diazoles; Hydrogenated 1,3-diazoles - A01N 43/54: 1,3-Diazines; Hydrogenated 1,3-diazines - A61P 31/04: Antibacterial agents - C07D 233/50: with carbocyclic radicals directly attached to said nitrogen atoms - C07F 3/003: {without C-Metal linkages} - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS - A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS - C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22) ## Abstract The invention relates to novel 2-aryliminohexahydropyrimidines and imidazolidines, of the formula ##STR1## as well as to salts and complexes thereof, having fungicidal activity. These compounds are particularly active against rust of beans, brown rust of wheat and mildew on cereals. After having been processed into compositions, the compounds of the invention can successfully be used to prevent or control mould infections in agriculture and horticulture in a dosage of 200-1000 g of active substance per hectare. Very active fungicides are, for example, 2-(4-cyclohexyl-phenyl) iminohexahydropyrimidine and 2-(4-n-hexyl-phenyl) iminohexahydropyrimidine, as well as the sulphuric acid salts of these compounds and complexes with zinc salts. ## Claims ### Claim 1 A compound of the formula: ##STR22## wherein R.sub.1 or R.sub.2 equal or different and represent any of a hydrogen atom, a C.sub.4 -C.sub.12 alkyl group, a C.sub.4 -C.sub.12 alkyloxy group, a C.sub.4 -C.sub.12 alkylthio group, a C.sub.3 -C.sub.7 cycloalkyl group, a benzyloxy group, a benzylthio group, a phenoxy group, a phenylthio group, a benzyloxy group substituted with halogen or C.sub.1 -C.sub.4 alkyl, a benzylthio group substituted with halogen or C.sub.1 -C.sub.4 alkyl, a phenoxy group substituted with halogen or C.sub.1 -C.sub.4 alkyl, a phenylthio group substituted with halogen or C.sub.1 -C.sub.4 alkyl, a C.sub.7 -C.sub.11 phenylalkyl group, a C.sub.7 -C.sub.11 phenylalkyl group substituted with halogen, benzyl, di(C.sub.1 -C.sub.6 alkyl)amino, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, halo C.sub.1 -C.sub.6 alkyl, halo C.sub.1 -C.sub.6 alkoxy, or halo C.sub.1 -C.sub.6 alkylthio; furyl C.sub.1 -C.sub.4 alkyl, thienyl C.sub.1 -C.sub.4 alkyl, di(C.sub.2 -C.sub.6 alkyl)amino, or C.sub.4 -C.sub.12 alkoxycarbonyl, or wherein R.sub.1 and R.sub.2 together represent a trimethylene or tetramethylene group with the proviso that R.sub.1 and R.sub.2 are not both hydrogen atoms, R.sub.3, R.sub.4, R.sub.7, and R.sub.8 are equal or different and represent any of a hydrogen atom or C.sub.1 -C.sub.4 alkyl, and R.sub.5 and R.sub.6 are equal or different and represent any of a hydrogen atom, C.sub.1 -C.sub.4 alkyl, or C.sub.2 -C.sub.5 alkanoyl, and salts or complexes thereof. ### Claim 2 (depends on 1) The compound of claim 1 which is 2-[4-{2-(4-benzylphenyl)ethyl}phenyl]imino-hexahydropyrimidine. ### Claim 3 A compound of the formula: ##STR23## wherein R.sub.15 is a C.sub.4 -C.sub.12 alkyl group, a C.sub.4 -C.sub.12 alkylthio group, cyclohexyl, phenylthio, a phenylthio group substituted with halogen or C.sub.1 -C.sub.4 alkyl, C.sub.7 -C.sub.11 phenylalkyl, a C.sub.7 -C.sub.11 phenylalkyl group wherein the phenyl group is substituted with halogen, C.sub.1 -C.sub.6 alkyl, or C.sub.1 -C.sub.6 alkoxy; furyl C.sub.1 -C.sub.4 alkyl, or C.sub.4 -C.sub.12 alkoxycarbonyl, and salts and complexes thereof. ### Claim 4 2-(4-cyclohexylphenyl)imino-hexahydropyrimidine. ### Claim 5 2-(4-n-octylphenyl)imino-hexahydropyrimidine. ### Claim 6 2-(4-n-butylphenyl)imine-hexahydropyrimidine. ### Claim 7 2-(4-n-hexylphenyl)imino-hexahydropyrimidine. ### Claim 8 2-(4-n-butylthiophenyl)imino-hexahydropyrimidine. ### Claim 9 2-(4-n-hexylthiophenyl)imino-hexahydropyrimidine. ### Claim 10 2-[4-(4-methylphenylthio)phenyl]imino-hexahydropyrimidine. ### Claim 11 2-[4-(4-chlorophenylthio)phenyl]imino-hexahydropyrimidine. ### Claim 12 2-(4-n-hexyloxycarbonylphenyl)imino-hexahydropyrimidine. ### Claim 13 2-(4-n-octyloxycarbonylphenyl)imino-hexahydropyrimidine. ### Claim 14 2-(4-n-heptylphenyl)imino-hexahydropyrimidine. ### Claim 15 2-(4-n-nonylphenyl)imino-hexahydropyrimidine. ### Claim 16 2-[4-(2-phenylethyl)phenyl]imino-hexahydropyrimidine. ### Claim 17 2-[4-{2-(4-chlorophenyl)ethyl}phenyl]iminohexahydropyrimidine. ### Claim 18 2-[4-{2-(4-methylphenyl)ethyl}phenyl]iminohexahydropyrimidine. ### Claim 19 2-[4-{2-(4-isopropylphenyl)ethyl}phenyl]iminohexahydropyrimidine. ### Claim 20 2-[4-(2-furylethyl)phenyl]imino-hexahydropyrimidine. ### Claim 21 2-(4-cyclohexylphenyl)imino-hexahydropyrimidine sulphate. ### Claim 22 2-(4-cyclohexylphenyl)imino-hexahydropyrimidine cinnamate. ### Claim 23 2-(4-cyclohexylphenyl)imino-hexahydropyrimidine.beta.-chlo roethanephosphonate. ### Claim 24 2-(4-cyclohexylphenyl)imino-hexahydropyrimidine p-dodecylbenzene sulphonate. ### Claim 25 2-(4-cyclohexylphenyl)imino-hexahydropyrimidine acetate. ### Claim 26 2-(4-cyclohexylphenyl)imino-hexahydropyrimidine zinc chloride complex. ### Claim 27 2-(4-cyclohexylphenyl)imino-hexahydropyrimidine zinc acetate complex. ### Claim 28 A fungicidal composition comprising a fungicidally effective amount of a compound of the formula: ##STR24## wherein R.sub.1 or R.sub.2 are equal or different and represent any of a hydrogen atom, a C.sub.4 -C.sub.12 alkyl group, a C.sub.4 -C.sub.12 alkyloxy group, a C.sub.4 -C.sub.12 alkylthio group, a C.sub.3 -C.sub.7 cycloalkyl group, a benzyloxy group, a benzylthio group, a phenoxy group, a phenylthio group, a benzyloxy group substituted with halogen or C.sub.1 -C.sub.4 alkyl, a benzylthio group substituted with halogen or C.sub.1 -C.sub.4 alkyl, a phenoxy group substituted with halogen or C.sub.1 -C.sub.4 alkyl, a phenylthio group substituted with halogen or C.sub.1 -C.sub.4 alkyl, a C.sub.7 -C.sub.11 phenylalkyl group, a C.sub.7 -C.sub.11 phenylalkyl group substituted with halogen, benzyl, di(C.sub.1 -C.sub.6 alkyl)amino, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, halo C.sub.1 -C.sub.6 alkyl, halo C.sub.1 -C.sub.6 alkoxy, or halo C.sub.1 -C.sub.6 alkylthio; furyl C.sub. 1 -C.sub.4 alkyl, thienyl C.sub.1 -C.sub.4 alkyl, di(C.sub.2 -C.sub.6 alkyl)amino, or C.sub.4 -C.sub.12 alkoxycarbonyl, or wherein R.sub.1 and R.sub.2 together represent a trimethylene or tetramethylene group with the proviso that R.sub.1 and R.sub.2 are not both hydrogen atoms, R.sub.3, R.sub.4, R.sub.7, and R.sub.8 are equal or different and represent any of a hydrogen atom or C.sub.1 -C.sub.4 alkyl, and R.sub.5 and R.sub.6 are equal or different and represent any of a hydrogen atom, C.sub.1 -C.sub.4 alkyl, or C.sub.2 -C.sub.5 alkanoyl, and salts or complexes thereof and an inert finely divided carrier therefor. ### Claim 29 (depends on 28) The fungicidal composition of claim 28 wherein said compound is 2-[4-{2-(4-benzylphenyl)ethyl}phenyl]imino-hexahydropyrimidine. ### Claim 30 (depends on 28) A composition as claimed in claim 28, characterized in that the active constituent is 2-(4-cyclohexylphenyl)imino-hexahydropyrimidine. ### Claim 31 (depends on 28) A composition as claimed in claim 28, characterized in that the active constituent is 2-(4-n-octylphenyl)imino-hexahydropyrimidine. ### Claim 32 (depends on 28) A composition as claimed in claim 28, characterized in that the active constituent is 2-(4-n-butylphenyl)imino-hexahydropyrimidine. ### Claim 33 (depends on 28) A composition as claimed in claim 28, characterized in that the active constituent is 2-(4-n-hexylphenyl)imino-hexahydropyrimidine. ### Claim 34 (depends on 28) A composition as claimed in claim 28, characterized in that the active constituent is 2-(4-n-butylthiophenyl)imino-hexahydropyrimidine. ### Claim 35 (depends on 28) A composition as claimed in claim 28, characterized in that the active constituent is 2-(4-n-hexylthiophenyl)imino-hexahydropyrimidine. ### Claim 36 (depends on 28) A composition as claimed in claim 28, characterized in that the active constituent is 2-[4-(4-methylphenylthio)phenyl]imino-hexahydropyrimidine. ### Claim 37 (depends on 28) A composition as claimed in claim 28, characterized in that the active constituent is 2-[4-(4-chlorophenylthio)phenyl]imino-hexahydropyrimidine. ### Claim 38 (depends on 28) A composition as claimed in claim 28, characterized in that the active constituent is 2-(4-n-hexyloxycarbonylphenyl)imino-hexahydropyrimidine. ### Claim 39 (depends on 28) A composition as claimed in claim 28, characterized in that the active constituent is 2-(4-n-octyloxycarbonylphenyl)imino-hexahydropyrimidine. ### Claim 40 (depends on 28) A composition as claimed in claim 28, characterized in that the active constituent is 2-(4-n-heptylphenyl)imino-hexahydropyrimidine. ### Claim 41 (depends on 28) A composition as claimed in claim 28, characterized in that the active constituent is 2-(4-n-nonylphenyl)imino-hexahydropyrimidine. ### Claim 42 (depends on 28) A composition as claimed in claim 28, characterized in that the active constituent is 2-[4-(2-phenylethyl)phenyl]imino-hexahydropyrimidine. ### Claim 43 (depends on 28) A composition as claimed in claim 28, characterized in that the active constituent is 2-[4-{2-(4-chlorophenyl)ethyl}phenyl]imino-hexahydropyrimidine. ### Claim 44 (depends on 28) A composition as claimed in claim 28, characterized in that the active constituent is 2-[4-{2-(4-methylphenyl)ethyl}phenyl]imino-hexahydropyrimidine. ### Claim 45 (depends on 28) A composition as claimed in claim 28, characterized in that the active constituent is 2-[4-{2-(4-isopropylphenyl)ethyl}phenyl]imino-hexahydropyrimidine. ### Claim 46 (depends on 28) A composition as claimed in claim 28, characterized in that the active constituent is 2-[4-(2-furylethyl)phenyl]imino-hexahydropyrimidine. ### Claim 47 (depends on 28) A composition as claimed in claim 28, characterized in that the active constituent is 2-(4-cyclohexylphenyl)imino-hexahydropyrimidine sulphate. ### Claim 48 (depends on 28) A composition as claimed in claim 28, characterized in that the active constituent is 2-(4-cyclohexylphenyl)imino-hexahydropyrimidine cinnamate. ### Claim 49 (depends on 28) A composition as claimed in claim 28, characterized in that the active constituent is 2-(4-cyclohexylphenyl)imino-hexahydropyrimidine.beta.-chloroethane phosphate. ### Claim 50 (depends on 28) A composition as claimed in claim 28, characterized in that the active constituent is 2-(4-cyclohexylphenyl)imino-hexahydropyrimidine p-dodecylbenzene sulphonate. ### Claim 51 (depends on 28) A composition as claimed in claim 28, characterized in that the active constituent is 2-(4-cyclohexylphenyl)imino-hexahydropyrimidine acetate. ### Claim 52 (depends on 28) A composition as claimed in claim 28, characterized in that the active constituent is 2-(4-cyclohexylphenyl)imino-hexahydropyrimidine zinc chloride complex. ### Claim 53 (depends on 28) A composition as claimed in claim 28, characterized in that the active constituent is 2-(4-cyclohexylphenyl)imino-hexahydropyrimidine zinc acetate complex. ### Claim 54 A fungicidal composition comprising a fungicidally effective amount of a compound of the formula: ##STR25## wherein R.sub.15 is a C.sub.4 -C.sub.12 alkyl group, a C.sub.4 -C.sub.12 alkylthio group, cyclohexyl, phenylthio, a phenylthio group substituted with halogen or C.sub.1 -C.sub.4 alkyl, C.sub.7 -C.sub.11 phenylalkyl, a C.sub.7 -C.sub.11 phenylalkyl group wherein the phenyl group is substituted with halogen, C.sub.1 -C.sub.6 alkyl, or C.sub.1 -C.sub.6 alkoxy; furyl C.sub.1 -C.sub.4 alkyl, or C.sub.4 -C.sub.12 alkoxycarbonyl, and salts and complexes thereof and an inert finely divided carrier therefor. ### Claim 55 (depends on 28) A method of preventing or combating mould infections in agriculture and horticulture, comprising treating the crop to be protected or the infected crop with a composition of claim 28 in a dosage of from 200 g to 1000 g of active substance per ha.