Phytotoxicity of New Furan-derived Aminophosphonic Acids, N-Aryl Furaldimines and 5-Nitrofuraldimine

作者：Matusiak Agnieszka; Lewkowski Jaroslaw^*; Rychter Piotr; Biczak Robert

来源：Journal of Agricultural and Food Chemistry, 2013, 61(32): 7673-7678.

DOI：10.1021/jf402401z

• furfuraldimines
• S-nitrofurfuraldimine
• Schiff bases
• aminophosphonic acids
• phytotoxicity test
• environmental protection
• ecotoxicology
• OECD standard

The aim of this work was to synthesize selected furaldimines and their aminophosphonic derivatives and evaluation the phytotoxicity of new obtained products according to OECD 208 Guideline. Four Schiff bases, N-furfurylidene-p-anisidine (la), N-furfurylidene-p-toluidine (1b), N-furfurylidene-benzhydrylamine (1c), and N-(2-nitrofurfurylidene)-p-toluidine (Id) were synthesized and three new furan-derived N-substituted aminomethylphosphonic acids, namely: 2-furyl N-(p-methoxyphenyl)-aminomethylphosphonic acid (2a), 2-furyl N-(p-methylphenyl)-aminomethylphosphonic acid (2b) and 2-furyl N-(diphenylmethyl)-aminomethylphosphonic acid (2c) were synthesized by the addition of in situ generated bis-(trimethylsilyl) phosphite to azomethine bond of corresponding Schiff bases 1a-c. Three Schiff bases 1a-b and 1d as well as all three aminophosphonic acids 2a-c were analyzed in regard with their phytotoxicity toward two plants, radish (Raphanus sativus) and oat (Avena sativa).
It has been found that tested N-furfurylidene-p-anisidine (la), N-(2-nitrofurfurylidene)-p-toluidine (Id) and aminophosphonic acids 2a c are toxic for selected plants. N-furfurylidene-p-toluidine (1b) did not show any ecotoxicological impact in used plant growth test.

• 出版日期2013-8-14