title: Phytotoxicity of new furan-derived aminophosphonic acids, N-aryl furaldimines and 5-nitrofuraldimine.
abstract: 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 (1a), N-furfurylidene-p-toluidine (1b), N-furfurylidene-benzhydrylamine (1c), and N-(2-nitrofurfurylidene)-p-toluidine (1d) 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 (1a), N-(2-nitrofurfurylidene)-p-toluidine (1d) 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.
authors.affiliation: Department of Organic Chemistry, Faculty of Chemistry, University of Łódź , Tamka 12, 91-403 Łódź, Poland.
authors.forename: Agnieszka
authors.initials: A
authors.lastname: Matusiak
authors.forename: Jarosław
authors.initials: J
authors.lastname: Lewkowski
authors.forename: Piotr
authors.initials: P
authors.lastname: Rychter
authors.forename: Robert
authors.initials: R
authors.lastname: Biczak
mesh_terms: D018554:Avena / Q000187:drug effects* / Q000254:growth & development; D005663:Furans / Q000737:chemistry* / Q000633:toxicity*; D015394:Molecular Structure; D010757:Phosphorous Acids / Q000737:chemistry / Q000633:toxicity*; D031224:Raphanus / Q000187:drug effects* / Q000254:growth & development
chemical_list: D005663:Furans; D010757:Phosphorous Acids; C570063:phosphonic acid; C039281:furan