Abstract: Novel acylated hydrazinomethylphosphonic acids, hydrazinomethylphosphonates, hydrazinomethylphosphinic acids, hydrazinomethylphosphinates or hydrazinomethylphosphine oxides of formula I below are able as "antidotes" or "safeners" to protect cultivated plants from the phytotoxic action of herbicides. Suitable crops are preferably maize, sorghum, cereals, rice and soybeans and the herbicides employed are in particular chloroacetanilides.

Abstract: Novel acylated hydrazinomethylphosphonic acids, hydrazinomethylphosphonates, hydrazinomethylphosphinic acids, hydrazinomethylphosphinates or hydrazinomethylphosphine oxides of formula I below are able as "antidotes" or "safeners" to protect cultivated plants from the phytotoxic action of herbicides. Suitable crops are preferably maize, sorghum, cereals, rice and soybeans and the herbicides employed are in particular chloroacetanilides.The acylated hydrazinomethylphosphonates, hydrazinomethylphosphinates or hydrazinomethylphosphine oxides have the formula I ##STR1## wherein R.sub.1 and R.sub.2 are each independently hydroxy, alkyl, aryl, phenylalkyl, alkoxy, alkenyloxy, alkynyloxy, aryl or phenylalkoxy, the radicals of which may be substituted,R.sub.3 is a halogenated alkanoyl or alkenoyl radicalR.sub.

Abstract: Phenylsulfonamides of the formula ##STR1## in which X is a group ##STR2## Y is hydrogen, halogen, C.sub.1 -C.sub.5 -alkyl, trifluoromethyl, C.sub.2 -C.sub.5 -alkenyl, C.sub.2 -C.sub.5 -alkynyl, nitro, --COOR.sup.6 or --Q--R.sup.6, A is oxygen, sulfur, a direct bond, C.sub.1 -C.sub.5 -alkylene, C.sub.2 -C.sub.5 -alkenylene, C.sub.1 -C.sub.5 -halogenoalkylene or --NR.sup.7 --(CH.sub.2).sub.m --; --CH.sub.2 --NH--(CH.sub.2).sub.m ; --(CH.sub.2).sub.m --NR.sup.7 -- or --O--(CH.sub.2).sub.p --, --S--(CH.sub.2).sub.p --, --(CH.sub.2).sub.p --O-- or --(CH.sub.2).sub.p --S--, n is zero or one, G is oxygen or sulfur, R.sup.4 is C.sub.1 -C.sub.5 -alkoxy, C.sub.1 -C.sub.5 -halogenoalkoxy, C.sub.1 -C.sub.5 -alkylthio, C.sub.1 -C.sub.5 -alkyl, C.sub.1 -C.sub.5 -halogenoalkyl, phenyl or hydroxyl, R.sup.5 is hydrogen, C.sub.1 -C.sub.5 -alkoxy, C.sub.1 -C.sub.5 -halogenoalkoxy, C.sub.1 -C.sub.5 -alkylthio, C.sub.1 -C.sub. 5 -alkyl or hydroxyl, R.sup.6 is hydrogen, C.sub.1 -C.sub.5 -alkyl, C.sub.1 -C.sub.

Abstract: When applied as safeners, the haloacylaminoalkylphosphinates, haloacylaminoalkylphosphinates and haloacylaminoalkylphosphine oxides of the formula I below are able to protect cultivated plants from the phytotoxic effects of herbicides. Suitable crops are preferably sorghum, cereals, rice, maize and soya beans and the herbicides employed are chloroacetanilides and thiocarbamates.The haloacylaminoalkylphosphonates, haloacylaminoalkylphosphinates and haloacylaminoalkylphosphine oxides have the formula I ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.4 alkenyloxy, C.sub.2 -C.sub.4 alkynyloxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.8 alkoxyalkoxy or C.sub.1 -C.sub.4 cyanoalkoxy,R.sub.2 is hydrogen or a substitutent as defined for R.sub.1,R.sub.3 and R.sub.4 are each independently hydrogen, C.sub.1 -C.sub.4 alkyl or one of R.sub.3 and R.sub.4 is also a radical ##STR2## or both taken together with the carbon atom to which they are attached are also a C.sub.3 -C.sub.

Abstract: Novel phosphonic acid and phosphinic acid derivatives of the formula I ##STR1## wherein X is hydrogen or chlorine,n is 0 or 1,R.sup.1 and R.sup.2 are each independently hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 cyanoalkyl, or they are a phenyl radical, a phenyl-C.sub.1 -C.sub.4 alkyl radical or a naphthyl radical, each unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, nitro or cyano, andA is a C.sub.1 -C.sub.3 alkyl chain which may be substituted by one or two C.sub.1 -C.sub.2 alkyl radicals and/or by one or two phenyl radicals, with the proviso that R.sup.2 is not hydrogen if n is 0, have a good selective herbicidal activity. They are suitable for controlling monocot and dicot weeds pre- and postemergence in various crops of useful plants, e.g.

Abstract: The invention relates to N-phosphonomethylglycylhydroxamic acid of the formula I ##STR1## or of the tautomeric formula Ia ##STR2## and salts thereof with strong acids, organic nitrogen bases, alkali metal or alkaline earth metal ions, as well as complex salts with aluminium or heavy metal compounds. These compounds have herbicidal and plant growth-regulating properties.

Abstract: The present invention relates to (2-nitro-5-aryloxyphenylamino)alkylphosphonic, -alkylphosphinic and -alkylphosphonous acid derivatives of the general formula I ##STR1## wherein X is halogen, CF.sub.3, NO.sub.2, CN, CONH.sub.2 or CSNH.sub.2,Y is nitrogen or --CH.dbd.,R is hydrogen, C.sub.1 -C.sub.4 alkyl or aralkyl containing 1 to 4 carbon atoms in the alkyl moiety,R.sub.1 is C.sub.1 -C.sub.4 alkyl,R.sub.2 is C.sub.1 -C.sub.4 alkyl, phenyl or --PO(OR.sub.6).sub.2,R.sub.3 is hydrogen or C.sub.1 -C.sub.4 alkyl,R.sub.4 is hydrogen, C.sub.1 -C.sub.4 alkyl or a cation,R.sub.5 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, hydroxyl or an --O-cation group,R.sub.6 is hydrogen or C.sub.1 -C.sub.4 alkyl,m is a value from 0 to 3,n is 0 or 1,p is a value from 0 to 3, andq is 0 or 1,with the proviso that R.sub.1 and R.sub.3 taken together may also be an unsubstituted or substituted C.sub.1 -C.sub.

Abstract: The invention relates to novel 2-nitro-4- or -5-pyridyloxyphenylphosphonic acid derivatives of the formula ##STR1## wherein X is halogen or trifluoromethyl, Y is hydrogen or halogen, one of the two substituents A and E is a phosphonate group ##STR2## wherein R is C.sub.1 -C.sub.4 alkyl or hydrogen, and the other is a nitro group, including the metal salts thereof and the salts thereof with ammonium and organic nitrogen bases, and to the preparation and use thereof. These compounds may be used for controlling weeds, regulating plant growth, or as microbicides.

Abstract: (2-Nitro-5-aryloxy-phenylamino)-alkylphosphine oxide derivatives of the formula I ##STR1## wherein X is halogen, CF.sub.3, NO.sub.2, CN, CONH.sub.2 or CSNH.sub.2,Y is nitrogen or --CH.dbd.,R.sup.1 is hydrogen, C.sub.1 -C.sub.4 -alkyl, or aralkyl having 1-4 carbon atoms in the alkyl moiety,R.sup.2 is hydrogen or C.sub.1 -C.sub.4 -alkyl,R.sup.3 is hydrogen, C.sub.1 -C.sub.4 -alkyl, phenyl, benzyl or C.sub.1 -C.sub.4 -alkylbenzyl,R.sup.4 and R.sup.5 independently of one another are each C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.2 -C.sub.6 -alkoxyalkyl, or aralkyl having 1-4 carbon atoms in the alkyl moiety,m is zero to 3, andn is 1 to 3,have useful herbicidal properties.

Abstract: When applied as safeners, the haloacylaminoalkylphosphinates, haloacylaminoalkylphosphinates and haloacylaminoalkylphosphine oxides of the formula I below are able to protect cultivated plants from the phytotoxic effects of herbicides. Suitable crops are preferably sorghum, cereals, rice, maize and soya beans and the herbicides employed are chloroacetanilides and thiocarbamates.The haloacylaminoalkylphosphonates, haloacylaminoalkylphosphinates and haloacylaminoalkylphosphine oxides have the formula I ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.4 alkenyloxy, C.sub.2 -C.sub.4 alkynyloxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.8 alkoxyalkoxy or C.sub.1 -C.sub.4 cyanoalkoxy,R.sub.2 is hydrogen or a substituent as defined for R.sub.1,R.sub.3 and R.sub.4 are each independently hydrogen, C.sub.1 -C.sub.4 alkyl or one of R.sub.3 and R.sub.4 is also a radical ##STR2## or both taken together with the carbon atom to which they are attached are also a C.sub.3 -C.sub.

Abstract: Phosphorus-containing N-phenylsulfonyl-N'-pyrimidinylureas and N-phenylsulfonyl-N'-triazinylureas of the formula ##STR1## and the salts of these compounds with amines, alkali or alkaline earth metal bases or quaternary ammonium bases have good pre-emergence and post-emergence selective herbicidal and growth-regulating properties.In this formula, X is a group ##STR2## Y is hydrogen, halogen, C.sub.1 -C.sub.5 -alkyl, trifluoromethyl, C.sub.2 -C.sub.5, alkenyl, C.sub.2 -C.sub.5 -alkynyl, nitro, --COOR.sup.6 or --Q--R.sup.6, Z is nitrogen or the methine group, E is oxygen or sulfur, R.sup.1 is hydrogen or C.sub.1 -C.sub.5 -alkyl and R.sup.2 and R.sup.3 independently of one another are C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.3 -halogenoalkyl, C.sub.1 -C.sub.3 -halogenoalkoxy, cyclopropyl, amino, methylamino or dimethylamino, and A is oxygen, sulfur, C.sub.1 -C.sub.5 -alkylene, C.sub.2 -C.sub.5 -alkenylene, C.sub.1 -C.sub.5 -halogenoalkylene or --NR.sup.7 --(CH.sub.2).sub.m --; --CH.sub.

Abstract: The invention relates to novel azolyl-olefin derivatives of the general formula I ##STR1## wherein R.sub.1 is an azolyl group,R.sub.2 is C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.1 -C.sub.4 alkyl substituted by unsubstituted or substituted phenyl, C.sub.1 -C.sub.4 alkoxycarbonyl or C.sub.2 -C.sub.6 alkenyl, or is C.sub.3 -C.sub.8 cycloalkyl which is substituted by 1 to 4 C.sub.1 -C.sub.4 alkyl groups,R.sub.3 is C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.8 cycloalkyl which is substituted by 1 to 4 C.sub.1 -C.sub.4 alkyl groups, or is the --C(R.sub.4)(R.sub.5)--[CH(R.sub.4)].sub.n --X--R.sub.6 group, wherein n is 0 or 1 andR.sub.4 and R.sub.5, each independently of the other, are hydrogen or C.sub.1 -C.sub.4 alkyl,X is oxygen or sulfur,R.sub.6 is a radical selected from the group consisting of C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.

Abstract: The invention relates to novel 2-nitro-4- or -5-pyridyloxyphenylphosphonic acid derivatives of the formula ##STR1## wherein X is halogen or trifluoromethyl, Y is hydrogen or halogen, one of the two substituents A and E is a phosphonate group ##STR2## wherein R is C.sub.1 -C.sub.4 alkyl or hydrogen, and the other is a nitro group, including the metal salts thereof and the salts thereof with ammonium and organic nitrogen bases, and to the preparation and use thereof. These compounds may be used for controlling weeds, regulating plant growth, or as microbicides.

Abstract: The invention relates to novel herbicidally active and plant-growth regulating 2-substituted 5-phenoxyphenylphosphinic acid derivatives of the formula ##STR1## wherein R.sub.1 is an unsubstituted or substituted alkyl or aryl radical, R.sub.2 is a hydroxyl group, lower alkoxy, alkylthio, alkylamino, dialkylamino or chlorine, X is halogen or is selected from the group consisting of --CF.sub.3, --NO.sub.2 or --CN, n is 0 to 3, and Y is selected from the group consisting of --NO.sub.2, --NH.sub.2, --OH, --CN, or is halogen. Preferred compounds are 2-nitro-5-(2'-chloro-4'-trifluoromethylphenoxy)phenylalkylphosphinic acids and lower alkyl esters thereof. The invention also relates to the production of the novel phosphinic acid derivatives, starting from a 3,4-dinitrodiphenyl ether and reaction with a O,O-dialkylalkyl- or -arylphosphonite as first step.

Abstract: The present invention relates to novel herbicidal and plant growth-inhibiting 2-substituted 5-phenoxyphenylphosphonic acid derivatives of the formula ##STR1## wherein each of R.sub.1 and R.sub.2 independently is hydroxyl, lower alkoxy, lower alkylthio, alkylamino, dialkylamino, chlorine, benzyloxy or benzylthio, X is halogen or a --CF.sub.3, --NO.sub.2, --CN, --CONH.sub.2 or --CSNH.sub.2 group, n is 0 to 3, and Y is --OH, halogen, NO.sub.2, --CN, NH.sub.2, --NHCO--R, --NHCOOR or --NH--SO.sub.2 --R, wherein R is an unsubstituted or halogenated lower alkyl radical. Preferred compounds are 2-nitro-5-(2'-chloro-4'-trifluoromethylphenoxy)-phenylphosphonic acid and the lower dialkyl esters thereof. The invention also relates to the production of the novel phosphonic acid derivatives, starting from a 3,4-dinitrodiphenyl ether and reacting it with a trialkylphosphite as first step.

Abstract: The present invention relates to novel herbicidal and plant growth-inhibiting 2-substituted 5-phenoxyphenylphosphonic acid derivatives of the formula ##STR1## wherein each of R.sub.1 and R.sub.2 independently is hydroxyl, lower alkoxy, lower alkylthio, alkylamino, dialkylamino, chlorine, benzyloxy or benzylthio, X is halogen or a --CF.sub.3, --NO.sub.2, --CN, --CONH.sub.2 or --CSNH.sub.2 group, n is 0 to 3, and Y is --OH, halogen, NO.sub.2, --CN, NH.sub.2, --NHCO--R, --NHCOOR or --NH--SO.sub.2 --R, wherein R is an unsubstituted or halogenated lower alkyl radical. Preferred compounds are 2-nitro-5-(2'-chloro-4'-trifluoromethylphenoxy)-phenylphosphonic acid and the lower dialkyl esters thereof. The invention also relates to the production of the novel phosphonic acid derivatives, starting from a 3,4-dinitrodiphenyl ether and reacting it with a trialkylphosphite as first step.

Abstract: The invention relates to N-phosphonomethylglycylhydroxamic acid of the formula I ##STR1## or of the tautomeric formula Ia ##STR2## and salts thereof with strong acids, organic nitrogen bases, alkali metal or alkaline earth metal ions, as well as complex salts with aluminium or heavy metal compounds. These compounds have herbicidal and plant growth-regulating properties.

Abstract: The present invention relates to novel herbicidal and plant growth-inhibiting 2-substituted 5-phenoxyphenylphosphonic acid derivatives of the formula ##STR1## wherein each of R.sub.1 and R.sub.2 independently is hydroxyl, lower alkoxy, lower alkylthio, alkylamino, dialkylamino, chlorine, benzyloxy or benzylthio, X is halogen or a --CF.sub.3, --NO.sub.2, --CN, --CONH.sub.2 or --CSNH.sub.2 group, n is 0 to 3, and Y is --OH, halogen, NO.sub.2, --CN, NH.sub.2, --NHCO--R, --NHCOOR or --NH--SO.sub.2 --R, wherein R is an unsubstituted or halogenated lower alkyl radical. Preferred compounds are 2-nitro-5-(2'-chloro-4'-trifluoromethylphenoxy)-phenylphosphonic acid and the lower dialkyl esters thereof. The invention also relates to the production of the novel phosphonic acid derivatives, starting from a 3,4-dinitrodiphenyl ether and reacting it with a trialkylphosphite as first step.

Abstract: Aminomethylphosphonic acid is produced by reaction of a hexahydro-1,3,5-triazine-N,N',N"-tris-carboxylic acid ester of the formula ##STR1## wherein R is an alkyl group having 1 to 4 carbon atoms or a phenyl group, in the presence of a Lewis acid as catalyst, with an ester of the phosphorous acid of the formula ##STR2## wherein R.sub.1 is an alkyl group having 1 to 5 carbon atoms, a phenyl group, a benzyl group, the 2-cyanoethyl group or the 2,2,2-trichloroethyl group, to give an N-carboxyaminomethylphosphonic acid derivative of the formula ##STR3## and subsequent hydrolysis thereof in an aqueous medium and in the presence of a strong acid.Aminomethylphosphonic acid can be used as active substance for influencing plant growth, and as intermediate for producing herbicidal active substances.

Abstract: A process for the production of methylaminomethylphosphonic acid and its esters is disclosed. It comprises heating trimethylhexahydro-s-triazine with at least 3 moles of a sterically hindered secondary phosphite and if desired converting the resulting diester or salt thereof into a corresponding hemiester or the free methylaminomethylphosphonic acid.