Arylthioalkyl- and arylthioalkenylphosphonic acids and derivatives thereof useful as herbicidal agents
AssigneeAmerican Cyanamid Company
InventorsCharles M. Langevine, John M. Finn
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Abstract
The present invention provides arylthioalkyl- and arylthioalkenylphosphonic acids and derivatives thereof having the structural formula I ##STR1## Further provided are compositions and methods comprising those compounds for the control of undesirable plant species.
Claims24
A compound having the structural formula ##STR32## wherein Y is hydrogen or halogen;
- Z is NH.sub.2 or OR.sub.2 ;
- R.sub.2 is hydrogen, C.sub.1 -C.sub.4 alkylcarbonyl or benzoyl;
- n is an integer of 0, 1 or 2;
- W is --(CH.sub.2).sub.4 --, --CH.sub.2 CH.dbd.CHCH.sub.2 -- or --CH.sub.2 CH.sub.2 CH.dbd.CH--;
- and
- R and R.sub.1 are each independently hydrogen, C.sub.1 -C.sub.4 alkyl,
- C.sub.1 -C.sub.4 alkylcarbonyloxymethylene or an alkali metal, ammonium or organic ammonium cation, provided that where W is --(CH.sub.2).sub.4 -- and Z is NH.sub.2 then at least one of R and R.sub.1 is other than C.sub.1 -C.sub.4 alkyl.
A compound selected from the group consisting of
- {4-[(o-hydroxyphenyl)thio]-1-butenyl}phosphonic acid;
- {4-[(o-hydroxyphenyl)thio]-1-butenyl}phosphonic acid;
- dilithium {4-[(o-aminophenyl)thio]butyl}phosphonate;
- dipivalate ester of bis(hydroxymethyl) {4-[(o-hydroxy-phenyl)thio]butyl}phosphonate;
- {4-[(o-hydroxyphenyl)thio]butyl}phosphonic acid, compound with N N N',N'-tetramethylethylenediamine;
- {4-[(o-hydroxyphenyl)sulfinyl]butyl}phosphonic acid;
- {4-[(o-hydroxyphenyl)thio]butyl}phosphonic acid, aryl-butyrate ester;
- and mixtures thereof.
A mixture comprising a compound selected from the group consisting of
- {4-[(o-aminophenyl)thio]butyl}phosphonic acid;
- {4-[(o-hydroxyphenyl)sulfinyl]butyl}phosphonic acid;
- and
- {4-[(o-hydroxyphenyl)thio]-1-butenyl}phosphonic acid, in combination with an aliphatic or cycloaliphatic amine.
A herbicidal composition which comprises an inert solid or liquid carrier and a herbicidally effective amount of a compound having the structural formula ##STR33## wherein Y is hydrogen or halogen;
- Z is NH.sub.2 or OR.sub.2 ;
- R.sub.2 is hydrogen, C.sub.1 -C.sub.4 alkylcarbonyl or benzoyl;
- n is an integer of 0, 1 or 2;
- W is --(CH.sub.2).sub.4 --, --CH.sub.2 CH.dbd.CHCH.sub.2 -- or --CH.sub.2 CH.sub.2 CH.dbd.CH--;
- and
- R and R.sub.1 are each independently hydrogen, C.sub.1 -C.sub.4 alkyl, C1-C4alkylcarbonyloxymethylene or an alkali metal, ammonium or organic ammonium cation, provided that where W is --(CH.sub.2).sub.4 -- and Z is NH.sub.2 then at least one of R and R.sub.1 is other than C.sub.1 -C.sub.4 alkyl.
A method for controlling undesirable plant species which comprises applying to the foliage and stems of said plants a herbicidally effective amount of a compound having the structural formula ##STR34## wherein Y is hydrogen or halogen;
- Z is NH.sub.2 or OR.sub.2 ;
- R.sub.2 is hydrogen, C.sub.1 -C.sub.4 alkylcarbonyl or benzoyl;
- n is an integer of 0, 1 or 2;
- W is --(CH.sub.2).sub.4 --, --CH.sub.2 CH.dbd.CHCH.sub.2 -- or --CH.sub.2 CH.sub.2 CH.dbd.CH--;
- and
- R and R.sub.1 are each independently hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylcarbonyloxymethylene or an alkali metal, ammonium or organic ammonium cation.
Dependencies are inferred from the claim text.