Patent GB-1069240-A (GB)
Title: Imidazolyl phosphorus compounds
IPC: C07F9/6558
Filed: 1966-04-28
Abstract: Cutting oils contain as a fungicide a compound of formula <FORM:1069240/C4-C5/1> where each X is hydrogen, alkyl or phenyl, the total number of carbon atoms in all X subtituents being from 0 to 15, R represents phenyl, styryl, a heteroparaffinic amido radical selected from morpholino, thiomorpholino, piperidino, 1 - pyrrolidinyl, 1,2,3,6 - tetrahydro - 1 - pyridyl and 4 - substituted - 1 - piperazinyl where the substituent is alkyl, phenyl or acetyl, an N-hetero-aromatic amido radical of formula <FORM:1069240/C4-C5/2> where Q is a group which with the nitrogen atom forms a ring of 5 atoms of which at least 2 are nitrogen and one is carbon and in which each carbon atom carries a hydrogen, alkyl or phenyl group, the total number of carbon atoms on all substituents on ring carbon atoms being from 0-15, or a group <FORM:1069240/C4-C5/3> , where G is alkyl or G11, G1 is phenyl, alkylphenyl or G11, and G11 is phenylalkyl (alkylphenyl)-alkyl, furfuryl tetrahydrofurfuryl, or (4-pyridylmethyl), R1 represents di-(C1-C4 alkyl)-amido or R, or R and R1 taken together represent a group of formula <FORM:1069240/C4-C5/4> where Z represents o-phenylene, or C2-3 alkylene and Z1 represents alkyl, phenyl or phenylalkyl.ALSO:Novel compounds of the formula <FORM:1069240/C2/1> where each X is hydrogen, alkyl or phenyl, the total number of C atoms in all X substituents being an integer of from 0 to 15, R represents phenyl, styryl, a heteroparaffinic amino radical selected from morpholino, thiomorpholino, piperidino, 1 - pyrrolidinyl, 1,2,3,6 - tetrahydro-1 - pyridyl, and 4 - substituted - 1 - piperazinyl where the substituent is alkyl, phenyl or acetyl, an N-heteroaromatic amido radical of formula <FORM:1069240/C2/2> where Q is a group which with the N atom forms a ring which has 5 ring atoms of which at least 2 are nitrogen and one is carbon and in which each C atom carries a hydrogen, alkyl or phenyl group, the total number of carbon atoms of all substituents on ring carbon atoms being from 0 to 15, or a group <FORM:1069240/C2/3> , where G is alkyl or G11, G1 is phenyl, alkylphenyl or G11, and G11 is phenylalkyl, (alkylphenyl) alkyl, furfuryl, tetrahydrofurfuryl, or (4-pyridylmethyl), R1 represents di (C1-C4 alkyl) amido or R, or R and R1 taken together represent a group of formula <FORM:1069240/C2/4> where Z represents o-phenylene or C2- 3 alkylene and Z1 represents alkyl, phenyl or phenylalkyl, where each alkyl group has from 1-4 carbon atoms, are prepared by reacting a phosphorothioic chloride of formula (R)(R1)P(S).Cl with an appropriate imidazole compound.  The reaction is suitably carried out in the presence of a inert liquid reaction medium, preferably organic, and in the presence of a hydrogen chloride acceptor at temperatures between 0 DEG  and 60 DEG  C. Suitable reaction media are hydrocarbons, ethers and tertiary amines.  The compounds may also be prepared (a) by reacting a phosphorothioic dichloride of formula (di (C1-C4 alkyl) amido)-P(=S)Cl2 or R(Cl)P(=S)Cl with an imidazole compound to form a corresponding imidazolyl phosphorothioic chloride intermediate and reacting this, in the presence of a hydrogen chloride acceptor, with an appropriate amino compound; or (b) by reacting PSCl3, preferably in the presence of a hydrogen chloride acceptor, with an imidazole compound to form a product in which R and R1 are both a hetero-aromatic amido group identical with the imidazolyl residue of the first formula above. Alternative method (a) is suitable for all products wherein not more than one of R and R1 is phenyl or styryl.  The compounds have fungicidal properties.ALSO:Fungicidal compositions useful in the protection and preservation of plants contain as active ingredient a compound of formula <FORM:1069240/A5-A6/1> where each X is hydrogen, alkyl or phenyl, the total number of carbon atoms in all X substituents being from 0 to 15.  R represents phenyl, styryl, a heteroparrafinic amido radical selected from morpholine, thiomorpholine, piperidino, 1-pyrrolidinyl, 1,2,3,6-tetrahydro-1-pyridyl, and 4-substituted-1-piperazinyl where the substituent is alkyl, phenyl or ocetyl, an N-heteroaromatic amido radical of formula <FORM:1069240/A5-A6/2> where Q is a group which with the N atom forms a ring of 5 atoms of which at least 2 are nitrogen and one is carbon and in which each C atom carries a H, alkyl or phenyl group, the total number of carbon atoms in all substituents or ring carbon atoms being from O to 15, or a group G-N\sv-G\sv were G is alkyl or G\yF, G\sv is phenyl, alkyl phenyl or G\yF, and G\yF is phenylalkyl (alkylphenyl) alkyl, furfuryl, tetra-hydrofurfuryl, or (4-pyridlylmethyl), R\sv represents di (C1-C4 alkyl) amido or R, or R and R\sv taken together represent a group of formula <FORM:1069240/A5-A6/3> where Z represents o-phenylene, or C2-3 alkylene, and Z\sv represents alkyl, phenyl or phenylalkyl. Compositions may take the form of liquids, powders and dusts with conventional carriers. Surface active dispersing agents may also be present.