Peter J. Diel

ORGANIC PHOSPHORUS COMPOUNDS 941 PREPARATION, PHYSICAL AND BIOLOGICAL PROPERTIES OF AMINO-ARYLMETHYLPHOSPHONIC- AND-PHOSPHONOUS ACIDS

Abstract The preparation, physical and spectroscopic properties of amino-arylmethylphosphonic- and -phosphonous acids, the phosphorus analogues of phenylglycine, are described. It is shown that several of the compounds prepared exhibit antifungal activity at 200 ppm. Thus 1e, 1f, 1g and 1h showed activity against Erysiphe (barley), 2a against Puccinia (wheat) and 6a against Botrytis (apple). Of particular interest is the high gameticidal activity of 3a in the greenhouse.

ORGANIC PHOSPHORUS COMPOUNDS 97.1 SYNTHESIS AND PROPERTIES OF 1-AMINO-2-ARYL- AND 2-PYRIDYL-ETHYLPHOSPHONIC ACIDS AND DERIVATIVES

Abstract 1-Amino-2-(o, m, and p-pyridyl)-ethylphosphonic acids, 5α, 5β and 5γ, have been prepared by alkylation of benzylideneaminomethylphosphonate, followed by hydrogenation and hydrolysis, whereas 1-amino- 2-(o, m, and p-methoxyphenyl)-ethyl phosphonic acids, 5i, 5k, and 51 and some other derivatives were obtained from the oximes by hydrogenation and hydrolysis. 1-Amino-2-pyridylethylphosphonic acids, 5α, 5β, and 5γ, and 1-amino-2-(alkoxy-substituted phenyl)- ethylphosphonic acids, 51, 5m, and 5n and others such as 5u show activity against Botrytis cinerea (on apple) and Cercospora (on peanuts). 5q is an inhibitor of anthocyanin synthesis in vivo. 3t exhibits activity against Piricularia (on rice) and 3w is active against Phytophthora (on tomato) and Plasmopora (on grapes).

ORGANISCHE PHOSPHORVERBINDUNGEN 78 HERSTELLUNG UND EIGENSCHAFTEN VON N-PHOSPHONOMETHYLGLYCIN DERIVATEN

Abstract The synthesis and the chemical, physical and spectral properties of glycino-N-methylphosphonic acid derivatives, i.e., 1-(N-carbethoxymethyl)-aminocyclopropan-1-phosphonic acid (5), 2-dihydroxyphosphonyl-N-carboxymethylpyrrolidine (10), 5-dihydroxyphosphonylproline (13), 2-carboxy-6-dihydroxy-phosphonyl-piperidine (16), N-(dihydroxyphosphonylmethyl)-proline (18a), N-(dihydroxyphosphonyl-methyl)-piperidin-2-carbonic acid (18b), N-phosphonomethylsubstituted-1-aminocyclopropyl-1-carbonic acid derivatives (21, 22, 23, 24), and 1-(N-dihydroxyphosphonylmethyl)-aminocyclohexan-1-carbonic acid (26) are described. None of these compounds showed herbicidal or plant growth regulator properties. 1-Aminocyclopropyl-1-phosphonic acid (3c) releases ethylene in the presence of oxidizing agents.

ORGANIC PHOSPHORUS COMPOUNDS 1051 SYNTHESIS AND PROPERTIES OF 2-AMINO-2-ARYLETHYLPHOSPHONIC ACIDS AND DERIVATIVES

Abstract 2-Amino-2-arylethylphosphonic acids, 6a to 6q have been prepared from the corresponding 2-acetoxyimino-or 2-methoxyimino-2-aryl-ethylphosphonates, 3 or 4, by hydrogenation using Raney-Ni as a catalyst, followed by hydrolysis with HCl. 3 and 4 were obtained from the corresponding aryl-bromomethyl-ketoxime-O-acetates, 1, or aryl-bromomethyl-O-methylketoximes, 2, by an Arbuzov reaction with triethylphosphite. Several of the 2-amino-2-arylethylphosphonic acids 6 show activity against Botrytis cinerea and Cercospora. Among the more active compounds were 6a, 6b, 6g and 6k, whereby 6b and 6k gave full protection against Botrytis cinerea (on apple) down to 60 ppm. The same compounds show also a weak inhibition of anthocyanin synthesis in vivo.

ORGANISCHE PHOSPHORVERBINDUNGEN 791 HERSTELLUNG UND EIGENSCHAFTEN VON α-AMINO-ω-CARBOXYALKYLPHOSPHON-UND-PHOSPHINSÄUREN

Abstract The synthesis, chemical and spectral properties of α-amino-ω-carboxyalkylphosphonic acids, (HO)2P(O)CH(NH2)(CH2) x CO2H, x = 2 to 6, and of α-amino-ω-carboxyalkyl-methylphosphinic acids CH3(HO)P(O)CH(NH2)(CH2) x CO2H, x = 2 to 6 are described and the fungicidal activity of some of these derivatives is reported.

ORGANISCHE PHOSPHORVERBINDUNGEN 85.1 HERSTELLUNG, EIGENSCHAFTEN UND BIOLOGISCHE WIRKUNG VON N-AMINOGLYPHOSATE UND AZAGLYPHOSATE

Abstract The synthesis and the chemical, physical and spectral properties of N-aminoglyphosate ethylester (hydrazino-N′-carbethoxymethyl-N′-methylphosphonic acid) 4a, H2OPCH2N(NH2)CH2CO2C2H5, of hydrazino-N′-carbethoxymethyl-N′-methyl-P-methylphosphinic acid 4b, CH3(HO2)PCH2N(NH2)-CH2CO2C2H5, and of azaglyphosate ethylester (hydrazino-N-carbethoxymethyl-N-methyl-phosphonic acid 9, H2O3PCH2NHNHCH2CO2C2H5, are described. 4a, 9 and 10 exhibit plant growth regulating properties.

ORGANIC PHOSPHORUS COMPOUNDS 92.1 SYNTHESIS AND PROPERTIES OF AZETIDINE-3-PHOSPHONIC- AND 3-PHOSPHONOUS ACID

Abstract Azetidine-3-phosphonic acid, 4a, and azetidine-3-phosphonous acid. 4b, have been prepared by the interaction of I-benzhydryl-3-methanesulfonato-azetidine with sodium phosphite or sodium O-ethyl-diethoxymethylphosphonite, followed by catalytic debenzhydrylation with HZ and hydrolysis. Neither acid shows biological activity.

ORGANIC PHOSPHORUS COMPOUNDS 871: SOME REACTIONS OF 0-ETHYL-2-CHLOROETHYLPHOSPHONITE

Abstract Primary and secondary amines react with O-ethyl-2-chloroethylphosphonite with the formation of 2-substituted aminoethylphosphonites, RR′NCH2CH2P(O)(OC2H5)H, 1. The reaction very likely proceeds through the intermediate formation of O-ethyl-vinylphosphonite. Hydrolysis of 1 produces the hydrochlorides of 2-substituted aminoethylphosphonous acids, RR′NCH2CH2PO2H2 2. These compounds interact with formaldehyde and benzylglycine to give the phosphinic acid derviatives 3, RR′NCH2CH2P(O)(OH)CH2N(CH2C6Hs)CH6CO2H, which upon debenzylation produce N-(2-substituted aminoethylphosphinylmethyl) glycines 4, RR′NCH2CH2P(O)(OH)CH2NHCH2C02H. The Mannich type reaction can also be performed with the half-esters 1 and with the acylated compounds 5a or 5b. This type of reaction has been used to prepare 2-aminoethyl-aminomethylphosphinic acid, H2NCH2CH2P(O)(OH)CH2NH2 8. Likewise, addition of acrylonitrile to 5b, followed by hydrogenation, hydrolysis and debenzylation gives 2-aminoethyl-3-aminopropylphosphinic acid, 12...

Organische phosphorverbindungen. LXXXVI: Herstellung und Eigenschaften von ϖ-phosphinyl-α-aminoalkyl-Carbonsäuren

Abstract The synthesis, chemical and spectral properties of ω-methylphosphinyl-α-aminoalkylcarbonic acids, CH3 (HO)P(O)(CH2)n CH(NH2)CO2H, n=3, 4, 5 or 6, are described. In contrast to the corresponding phosphonic acid derivatives these compounds exhibit no anticonvulsive and NMDA-antagonistic properties.

Synthesis and Properties of 2-Amino-2-Arylethylphosphonic Acids and Derivatives

ABSTRACT 2-Amino-2-arylethylphosphonic acids, 6a to 6q have been prepared from the corresponding 2-acetoxyimino- or 2-methoxy imino-2-arylethylphosphonates, 3 or 4, by hydrogenation using Raney-Ni as a catalyst, followed by hydrolysis with HCl. 3 and 4 were obtained from the corresponding aryl-bromomethyl-ketoxime-O-acetates, 1, or aryl-bromomethyl-O-methylketoximes, 2, by an Arbuzov reaction with triethylphosphite. Several of the 2-amino-2-arylethylphosphonic acids 6 show activity against Botrytis cinerea and Cercospora. Among the more active compounds were 6a, 6b, 6g and 6k, whereby 6b and 6k gave full protection against Botrytis cinerea (on apple) down to 60 ppm. The same compounds show also a weak inhibition of anthocyanin synthesis in vivo.1