ORGANIC PHOSPHORUS COMPOUNDS 88¹ SULFONIC- AND SULFINIC ACID ANALOGUES OF GLYPHOSATE

Abstract

Under alkaline conditions aminomethylphosphonic acid reacts with hydroxymethylsulfonic-and hydroxymethylsulfinic acid to give N-phosphonylmethyl-amino-methylsulfonic-, 1, Na₂O₃PCH₂NHCH₂SO₃Na, and N-phosphonylmethyl-aminomethylsulfinic acid trisodium salt, 2, Na₂O₃PCH₂NHCH₂SO₂Na, respectively. Glyphosate also interacts with the sulfur compounds and yields N-hydroxysulfonylmethyl- and N-hydroxysulfinylmethyl-glyphosate, 3,Na₂0₃PCH₂N(CH₂SO₃Na)CH₂C0₂Na and 4, Na₂O₃PCH₂N(CH₂SO₂Na)CH₂CO₂Na, respectively. Whereas 1 and 2 are biologically not active, 3 and 4 show herbicidal activity in post-application which is by a factor of 2 weaker than that of glyphosate.

Key Words:

• N-Phosphonylmethyl-aminomethylsulfonic acid
• N-phosphonylmethyl-aminomethylsulfinic acid
• N-hydroxysulfonylmethylglyphosate
• N-hydroxysulfinylmethyl-glyphosate