Abstract: A herbicidal compound having the structural formula ##STR1## where R is C.sub.1 -C.sub.10 alkyl and Y is C.sub.1 -C.sub.10 alkyl optionally substituted with halogen or N-(R').sub.2 where R' is C.sub.1 -C.sub.10 alkyl.
Abstract: A herbicidal compound having the structural formula ##STR1## where R is C.sub.1 -C.sub.10 alkyl; X is oxygen, sulfur, sulfoxide or sulfone; and Y is C.sub.1 -C.sub.6 alkyl, phenyl or substituted phenyl.
Abstract: A method of preparing N-phosphonomethylglycine comprising; (a) reacting N-hydroxymethyl haloacetamide with a chlorinating agent, preferably thionyl chloride to form N-chloromethyl haloacetamide; (b) reacting N-chloromethyl haloacetamide with a phosphite to form N-haloacetylaminomethyl phosphonate; (c) reacting the phosphonate with derivative of haloacetic acid to form N-haloacyl-N-(cyanomethyl or carboalkoxymethyl) phosphonate; and (d) hydrolyzing this later phosphonate to yield N-phosphonomethylglycine.
Abstract: A herbicidal compound having the structural formula ##STR1## wherein R is C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.8 cycloalkylalkyl wherein the alkyl has 1 to 6 carbon atoms, C.sub.3 -C.sub.10 alkenyl, C.sub.5 -C.sub.8 cycloalkenyl; benzyl or mono- or di-substituted benzyl wherein the substituents are C.sub.1 -C.sub.4 alkyl, halogen, nitro or C.sub.1 -C.sub.4 haloalkyl; R.sup.1 and R.sup.2 independently are C.sub.1 -C.sub.6 alkyl or aryl, or R.sup.1 and R.sup.2 together form a ring with the nitrogen to which they are attached having 3-8 carbon atoms, optionally substituted with one or two methyl groups.
Abstract: A herbicidal compound having the structural formula ##STR1## wherein R is hydrogen or C.sub.1 -C.sub.6 alkyl, substituted or unsubstituted phenyl; substituted or unsubstituted benzyl, preferably hydrogen or methyl; and R.sup.1 is hydrogen or C.sub.1 -C.sub.6 alkyl, preferably hydrogen or methyl.
Abstract: A process for preparing N-phosphonomethylglycine which comprises:(1) reacting a primary amine with formaldehyde to produce N,N',N"-tris-substituted-hexahydro-s-triazine;(2) reacting the triazine with an haloacetyl halide, preferably chloroacetyl chloride, to form the N-(substituted)-N-halomethyl acetamide of the haloacetyl halide;(3) reacting the amide with O,O-di-(substituted)-aminomethylphosphonate to form O,O-di-(substituted)-1-phosphonomethyl-3-(substituted)-1,3-imidazol-4-one; and(4) hydrolyzing the 1,3-imadazol-4-one to yield N-phosphonomethylglycine.
Abstract: Compounds having the structural formula ##STR1## wherein R is hydrogen or halogen, R.sup.1 is halogen, or trifluoromethyl R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl, and X is oxygen or methylene.
Abstract: A herbicidal compound having the structural formula ##STR1## wherein R.sup.1 is C.sub.1 -C.sub.4 alkyl; R.sup.2 is hydrogen or chlorine and X is halogen.
Abstract: A method of preparing N-phosphonomethylglycine comprising (a) reacting a triazine with an acyl halide to form the N-cyanomethyl-N-halomethyl amide of the acyl halide; reacting the said amide with a phosphite to form a phosphonate compound; and hydrolyzing said phosphonate to yield N-phosphonomethylglycine.
Abstract: A method of preparing N-phosphonomethylglycine comprising (a) reacting a substituted triazine with an acyl halide to form the N-carboalkoxymethyl-N-halomethyl amide of the acyl halide; reacting the said amide with a phosphite to form a phosphonate compound; and hydrolyzing said phosphonate to yield N-phosphonomethylglycine.
Abstract: 1-(Substituted phenylthiocarbamyl) 3,3-disubstituted formamidine compounds having the structural formula ##STR1## wherein n is 1, 2 or 3,R is alkyl having 1 to 6 carbon atoms, alkoxy having 1 to 6 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogen, nitro, acyl having 1 to 4 carbon atoms, hydroxyl and ##STR2## wherein R.sup.3 and R.sup.4 have the same meaning as R.sup.1 and R.sup.2 defined below,R.sup.1 and R.sup.2 are the same or different and are alkyl having 1 to 6 carbon atoms, or taken together represent the chain --(CH.sub.2).sub.p --(X).sub.m --(CH.sub.2).sub.q and forming a ring structure with the nitrogen to which they are bound wherein p is 1, 2 or 3, q is 2 or 3, X represents --O--, --S--, --SO--, --SO.sub.2 --, --NR.sup.3 --, R.sup.3 is hydrogen or alkyl having 1 to 6 carbon atoms, and m is 0 or 1 and their use as pharmaceutical agents.
Type:
Grant
Filed:
July 16, 1980
Date of Patent:
July 30, 1985
Assignee:
Stauffer Chemical Company
Inventors:
Ferenc M. Pallos, Jack R. DeBaun, Eugene G. Teach
Abstract: A method of preparing N-phosphonomethylglycine comprising reacting a compound having the structural formulaR--NHCH.sub.2 CNwherein R is tertiary butyl or ##STR1## wherein Ar is an aromatic group, R.sup.1 and R.sup.2 are independently hydrogen, C.sub.1 -C.sub.10 alkyl or an aromatic group, with formaldehyde and a phosphite to form a tertiary amine and hydrolyzing the tertiary amine in the presence of hydrochloric, hydrobromic, or hydriodic acid to yield N-phosphonomethylglycine.
Abstract: A compound having the following structural formula ##STR1## wherein R is nitro, chlorine or hydroxy, preferably nitro; R.sup.1 is C.sub.1 -C.sub.4 alkyl, preferably cyclopropyl or ethyl or alkylthio, preferably methylthio; and R.sup.2 is hydrogen or chlorine.
Abstract: A compound having the structural formula ##STR1## wherein R is C.sub.1 -C.sub.4 alkyl; R.sup.1 is C.sub.1 -C.sub.4 alkyl; R.sup.2 is hydrogen or methyl; R.sup.3 is methyl or ethyl; and R.sup.4 is C.sub.1 -C.sub.4 alkyl.
Abstract: A method for preparing N-phosphonomethylglycine comprising (a) O,O-dialkylaminomethylphosphonate with formaldehyde to produce a triazine; (b) reacting the triazine formed in step (a) with an acyl halide to form the O,O-dialkyl-N-phosphonomethyl-N-chloromethyl acetamide of the acyl halide; (c) reacting the amide formed in step (b) with metal cyanide to form O,O-dialkyl-N-cyanomethyl-N-acetamide; and (d) hydrolyzing the acetamide formed in step (c) to yield N-phosphonomethylglycine.
Abstract: Compounds having the structural formula ##STR1## wherein R is hydrogen or halogen, R.sup.1 is halogen, R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl, and X is oxygen or methylene useful as post-emergent herbicides against annual and perennial grasses.
Abstract: A method of preparing N-phosphonomethylglycine comprising (a) reacting a substituted triazine with an acyl halide to form the N-carboalkoxymethyl-N-halomethyl amide of the acyl halide; reacting the said amide with a phosphite to form a phosphonate compound; and hydrolyzing said phosphonate to yield N-phosphonomethylglycine.
Abstract: A method of preparing N-phosphonomethylglycine comprising (a) reacting a triazine with an acyl halide to form the N-cyanomethyl-N-halomethyl amide of the acyl halide; reacting the said amide with a phosphite to form a phosphonate compound; and hydrolyzing said phosphonate to yield N-phosphonomethylglycine.
Abstract: A method for preparing N-phosphonomethylglycine comprising (a) O,O-dialkylaminomethylphosphonate with formaldehyde to produce a triazine; (b) reacting the triazine formed in step (a) with an acyl halide to form the O,O-dialkyl-N-phosphonomethyl-N-chloromethyl acetamide of the acyl halide; (c) reacting the amide formed in step (b) with metal cyanide to form O,O-dialkyl-N-cyanomethyl-N-acetamide; and (d) hydrolyzing the acetamide formed in step (c) to yield N-phosphonomethylglycine.
Abstract: A method of preparing N-phosphonomethylglycine comprising: (a) reacting O,O-dialkylaminomethylphosphonate with formaldehyde to produce a triazine compound; (b) reacting the triazine formed in step (a) with an acyl cyanide to form the O,O-dialkyl-N-phosphonomethyl-N-cyanomethyl amide; and (c) hydrolyzing the amide formed in step (b) to yield N-phosphonomethylglycine.