Abstract: Novel herbicides are 3-(substituted) phenyl-2-(substituted imino)-1,3,4-dihydrothiadiazoles. Also disclosed are intermediates for such compounds, and processes for producing the herbicidal compounds and their intermediates.

Abstract: An iminooxazolidine having the formula ##STR1## wherein X and Y are the same or different and are selected from the group consisting of cyano, halogen, acyl, alkyl, alkylthio, haloalkyl, trihalomethylthio, alkylsulfenyl, alkoxy, carboalkoxy and trihalomethyl wherein the alkyl groups have from 1 to 5 carbon atoms;m is 1 or 2;n is 0, 1 or 2; andR is hydrogen or a lower alkyl group having from 1 to 3 carbon atoms, preferably an ethyl group, and herbicidally effective salts thereof.

Abstract: A process of the preparation of iminooxazolidines which comprises (a) reacting a urea alcohol of the formula ##STR1## X, Y, n and R are as defined, with a dehydrating agent to form an intermediate salt compound of the formula ##STR2## wherein X, Y, n and R are as previously defined and X.degree.

Abstract: A process for the preparation of cyclic urea compounds in which a substituted anilino alkanone is reacted with an arylsubstituted isocyanate to form an intermediate imidazoline compound, and said imidazoline compound is hydrogenated in the presence of suitable catalyst to form an imidazolidine of the formula ##STR1## wherein X, X', Y and Y' are the same or different and are selected from the group consisting of trifluoromethyl, chloro, bromo, fluoro, hydrogen, cyano, nitro, alkyl, thioalkyl, halothioalkyl, alkoxy and sulfonylalkyl wherein the alkyl groups have from 1 to 4 carbon atoms; and R is selected from the group consisting of hydrogen and alkyl having from 1 to about 4 carbon atoms. Also included are intermediate anilino alkanones and the process of making them.

Abstract: Compounds having the formula ##STR1## in which R is hydrogen, cyano or --COOR.sub.2 ; R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sub.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; and Z is ##STR2## in which A is halogen, B is halogen or hydrogen and Y is nitrogen or --CH--, are herbicides.

Abstract: A substituted oxazolidone compound having the formula ##STR1## wherein Ar.sup.1 and Ar.sup.2 are the same or different and are aromatic or a substituted aromatic group wherein the substituent is selected from chlorine, bromine, chloride or trifluoromethyl, and R is lower alkyl having from 1 to 6 carbon atoms.

Abstract: Herbicidally active thiolcarbamates are employed in combination with certain allyl amine salts of thiocarbamic acid compounds having the formula ##STR1## wherein R.sub.4 and R.sub.5 are independently selected from the group consisting of allyl, alkyl substituted allyl, and lower alkyl groups having from about 1 to about 6 carbon atoms;R.sub.6 and R.sub.7 are independently selected from the group consisting of allyl, alkyl substituted allyl, and lower alkyl groups having from about 1 to about 6 carbon atoms; andX is oxygen or sulfur wherein at least one of R.sub.4 and R.sub.5 and at least one of R.sub.6 and R.sub.7 is an allyl group. In a typical application, the allyl amine salt of thiocarbamic acid compound is included in sufficient quantity to lessen the rate of soil degradation of the thiolcarbamate. As a result, the herbicidal effectiveness of the thiolcarbamate is enhanced and prolonged, rendering single application of the herbicide effective over a longer period of time.

Abstract: Compounds having the formula ##STR1## in which Z is ##STR2## wherein X is hydrogen or halogen and Y is --CH or N; R is alkyl, phenyl, trihalomethylphenyl, cyanomethyl, carboalkoxymethyl, ##STR3## alkenyl; and R.sub.1 is hydrogen, lower alkyl, halo-(lower alkyl), or Z; and intermediate alkyl onium salts of the type ##STR4## in which R.sub.3 is C.sub.1 -C.sub.8 alkyl, G is nitrogen or phosphorus and Z' is ##STR5## wherein X is hydrogen or halogen and Y is --CH or N; are herbicides.

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: Herbicidally active thiocarbamates are employed in combination with certain unsaturated aryl sulfides, sulfoxides or sulfones having the formula ##STR1## in which R.sup.4 is hydrogen, halogen, C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 alkoxy; R.sup.5 is C.sub.2 -C.sub.6 haloalkenyl or C.sub.2 -C.sub.6 alkynyl; and n equals 0 or 2. In a typical application, the unsaturated aryl sulfide, sulfoxide or sulfone is included in sufficient quantity to lessen the rate of soil degradation of the thiocarbamate. As a result, the herbicidal effectiveness of the thiocarbamate is enhanced and prolonged, rendering a single application of the herbicide effective over a longer period of time.

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: 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 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: An herbicide antidote having the formula: ##STR1## in which X is selected from the group consisting of hydrogen and halogen wherein the halogen is chlorine, bromine or iodine.

Abstract: An herbicide antidote having the formula: ##STR1## in which X is selected from the group consisting of hydrogen and halogen wherein the halogen is chlorine, bromine or iodine.

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 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.