Phosphoric acid monoester salts, process for their preparation, and fungicidal compositions containing them as active ingredient

• US 4,661,477 A
• Filed: 09/29/1982
• Issued: 04/28/1987
• Est. Priority Date: 08/27/1980
• Status: Expired due to Fees

• Current Assignee: Borsodi Vegyi Kombinat
• Original Assignee: Borsodi Vegyi Kombinat
• Inventors: Kis, Gyorgy, Gaal, Sandor, Bodnar, Laszlo, Varga, Valeria M., Egyhazi nee Csizmadia, Eva, Tasnadi, Marta, Molnar, Janos, Toth, Bertalan, Kaptas, Tibor, Kajati, Istvan, Kocsis nee Bagi, Maria, Cserhati nee Botka, Ilona, Dudar, Erzsebet, Csete, Sandor, Gorog nee Privitzer, Katalin
• Primary Examiner(s): ROBINSON, ALLEN JAY
• Application Number:
  US06/426,949
• Time in Patent Office: 1,672 Days
• Field of Search: 424/199, 514/76
• US Class Current: 514/76
• CPC Class Codes: A01N 57/12 containing acyclic or cycloaliphatic radicals
• CPC Class Codes: A01N 57/14 containing aromatic radicals
• CPC Class Codes: C07F 9/141 Esters of phosphorous acids
• CPC Class Codes: C07F 9/142 with hydroxyalkyl compounds without further substituents on alkyl

Abstract

The invention relates to new compounds of the general formula I ##STR1## wherein R₁ is a straight or branched chained alkyl having 1 to 13 carbon atoms, optionally substituted with halogen, alkoxyalkyl containing 1 to 5 carbon atoms in the alkoxy and 1 to 4 carbon atoms in the alkyl moiety or phenyl;

R₂ is alkyl having 6 to 20 carbon atoms; alkoxyalkyl, phenoxyalkyl, furfuryl, cyclopropyl-alkyl, cyclopentyl, cycloheptyl, thiazolyl, triazolyl, thiazolinyl, pyridinyl, picolyl, benzimidazolyl, piperonyl, pirimidinyl, chlorobenzothiazolyl, benzyl, phenyl substituted with chloro and/or amino, or amino and alkyl, or amino and nitro groups, alkenyl, alkinyl, aminoalkyl, dialkylamino-alkyl, alkylaminoalkyl, alkylphosphonateammoniumalkyl, 3,5-dichlorophenyl-hidantoinyl, or thiadiazolyl optionally substituted with alkyl;

R₃ is hydrogen, phenyl, benzyl, alkenyl, alkyl, hydroxy, alkoxy or alkoxyalkyl; or

R₂ and R₃ together stand for a 3,5-dichlorophenyl-hidantoinyl group;

R₄ is hydrogen or alkyl optionally substituted with hydroxyl.

The new phosphoric acid monoester salts of the general formula I show fungicidal activity. The fungicidal compositions containing said compounds as active ingredients are also within the scope of the invention. According to a further aspect of the invention there is provided a process for the preparation of the new compounds.

Claims

1. A fungicidal composition comprising a material selected from the group consisting of carriers and surface active agents and a fungicidally effective amount of a compound of the formula I ##STR9## wherein R₁ is a straight or branched chained alkyl having 1 to 13 carbon atoms;

R₂ is alkoxyalkyl with 1 to 16 carbon atoms in the alkoxy portion and 1 to 4 carbon atoms in the alkyl portion, alkenyl having 2 to 4 carbon atoms, alkinyl having 2 to 4 carbon atoms, aminoalkyl wherein the alkyl portion has from 1 to 6 carbon atoms, alkylaminoalkyl wherein the alkyl portions have 1 to 4 carbon atoms, alkylphosphonate ammoniumalkyl wherein the alkylphosphonate portion has 1 to 4 carbon atoms in the alkyl portion and the remaining alkyl has 1 to 6 carbon atoms;

R₃ is hydrogen, alkenyl having 2 to 5 carbon atoms, and alkoxyalkyl wherein the alkoxy portion has 1 to 4 carbon atoms and the alkyl portion has 1 to 4 carbon atoms;

R₄ is hydrogen.

2. The fungicidal composition as claimed in claim 1 containing 1 to 95% by weight of active ingredient.

3. A method of treatment fungal diseases of plant, which comprises applying to the plants or to the habitat thereof a fungicidally effective amount of a compound of the formula I, wherein R₁, R₂, R₃ and R₄ are as defined in claim 1.