ORGANOPHOSPHORUS COMPOUNDS AS POTENTIAL FUNGICIDES. PART II. AMINOALKANE-, GUANIDINOALKANE-, AND THIOUREIDOALKANE-PHOSPHONIC ACIDS: PREPARATION, SPECTROSCOPY, AND FUNGICIDAL ACTIVITY

References

• Cameron , I. D. G. , Hudson , H. R. , Ojo , I. A. O. and Pianka , M. 1988 . Phosphorus Sulfur , 40 : 183 Part.
   Web of Science ®Google Scholar
• Hudson , H. R. , Ojo , I. A. O. and Pianka , M. 1986 . Internat. Pest Control , 28 : 148
   Google Scholar
• Cameron , D. G. , Hudson , H. R. , Lagerlund , I. , Pianka , M. and Stroemberg , A. 1986 . USP (to KenoGard AB),4 600 429 (15 Jul.cf. PCT Int. Appln. WO 85 00,038 (3 Jan 1985). Chem. Abstr. 103, 22780b (1985).
   Google Scholar
• Cameron , D. G. , Hudson , H. R. , Lagerlund , I. and Pianka , M. 1989 . Eur. Patent , 153 (to KenoGard AB),284 (30 Aug.cf. Eur. Pat. Appln. EP 153,284 (28 Aug 1985).Chem. Abstr. 104, 207445k (1986);
   Google Scholar
• Cameron , D. G. , Hudson , H. R. and Pianka , M. 1989 . Phosphorus Sulfur , 51/52 : 391 Proc. XI Internat. Conf. Phosphorus Chem., Tallinn, USSR, 3–7 July,1990. (It should be noted that the printed title for the Tallinn abstract is in error: “aminoalkyne” should read “aminoalkane”).
   Google Scholar
• Worthing , C. R. and Hance , R. J. , eds. 1991 . The Pesticide Manual—a World Compendium 33 “,”9th Edition, ed., British Crop Protection Council, Farnham, Surrey, p.
   Google Scholar
• Kidd , H. and James , D. R. , eds. 1991 . The Agrochemicals Handbook “,”3rd Edition, ed., Royal Society of Chemistry, Cambridge, A1282/Aug 91(.
   Google Scholar
• Redmore , D. 1976 . Topics in Phosphorus Chemistry Edited by: Griffith , E. J. and Grayson , M. Vol. 8 , 515 – 585 . in, vol., eds., Interscience, New York,pp.; K. A. Petrov, V. A. Chauzov and T. S. Erokhina, Russ. Chem. Rev. 43, 984 (1974); V. P. Kukhar and V. A. Solodenko, Russ. Chem. Rev. 56, 859 (1987); P. Mastalerz, “α-Substituted Phosphonates. P—C—N Systems,” in ch. 7, “Handbook of Organophosphorus Chemistry,” ed. R. Engel, Dekker, New York, N. Y., pp. 316–375 (1992).
   Google Scholar
• Oleksyszyn , J. and Tyka , R. 1977 . Tetrahedron Lett. , 32 : 2823
   Google Scholar
• Oleksyszyn , J. , Subotkowska , L. and Mastalerz , P. 1979 . Synthesis , : 985
   Web of Science ®Google Scholar
• Pikl , J. and Pitman , N. J. 1943 . (to du Pont), U. S. Patent 2 328 358(.Chem. Abstr. 38, 754 (1944).
   Google Scholar
• Chavane , V. 1947 . Compt. rend. , 224 : 406 . |The low melting point quoted in this paper for 2 (n = 4) indicates that the correct product had not been obtained|.
   Google Scholar
• Chavane , V. 1948 . Bull. Soc. Chim. Fr. , 27 : 774
   Google Scholar
• Oleksyszyn , J. , Tyka , R. and Mastalerz , P. 1977 . Synthesis , : 571
   Web of Science ®Google Scholar
• Moreaud , E. , Lacoste , A. M. and Neuzil , E. 1975 . Compt. rend., Sci. Ser. C. , 280 : 1309
   PubMedGoogle Scholar
• Oleksyszyn , J. , Tyka , R. and Mastalerz , P. 1979 . Pol. J. Chem. , 53 2129(.Chem. Abstr. 92, 181276 (1980).
   Google Scholar
• Adetunji , G. J. , Cameron , D. G. , Henrick , K. , Hudson , H. R. , McPartlin , M. , Pianka , M. , Mathey , F. , Robert , D. and Wolf , R. 1983 . Phosphorus Sulfur , 18 : 481 Proc. Internat. Conf. Phosphorus Chem., Nice, France, September, ed. J. G. Riess, 1983.
   Google Scholar
• Appleton , T. G. , Hall , J. R. , Harris , A. D. , Kimlin , H. A. and McMahon , I. J. 1984 . Aust. J. Chem. , 37 : 1833
   Web of Science ®Google Scholar
• Kudzin , Z. H. and Kotynski , A. 1980 . Synthesis , : 1028
   Web of Science ®Google Scholar
• Glowacki , Z. and Topolski , M. 1989 . Magn. Reson. Chem. , 27 : 897
   PubMed Web of Science ®Google Scholar
• Glowacki , Z. , Hoffmann , M. , Topolski , M. and Rachon , J. 1991 . Phosphorus, Sulfur, and Silicon , 60 : 67
   Web of Science ®Google Scholar
• Robitaille , P. M. L. , Robitaille , P. A. , Brown , G. G. Jr. and Brown , G. G. 1991 . J. Magn. Reson. , 92 : 73
   Web of Science ®Google Scholar
• Rachon , J. , Schöllkopf , U. and Wintel , T. 1981 . Annalen , : 709 Results obtained in the present studies are in accord with previous data given for 1 (R [dbnd] Me, Et, Prn, Bun). ||.
   Google Scholar
• Cameron , D. G. 1983 . The complexities of these 1H spectra have been referred to previously |cf.,Ph.D. thesis (CNAA), The Polytechnic of North London,;D. G. Cameron, H. R. Hudson and M. Pianka, Reference 4(b). A full analysis of selected examples will be given elsewhere|.
   Google Scholar
• Cameron , D. G. , Creaser , C. S. , Hudson , H. R. , Pianka , M. and Wright , H. 1984 . Chem. and Ind. , : 774
   Web of Science ®Google Scholar
• Bawa , F. , Cameron , D. G. , Creaser , C. S. , Hudson , H. R. , Pianka , M. , Shode , O. O. , Soares , V. M. , Volckman , J. F. , Knoll , F. and Ruppert , I. 1986 . Phosphorus Sulfur , 30 : 743 Proc. X Internat. Conf. Phosphorus Chem., Bonn, FRG, Aug 31-Sept. 6, ed. R. Appel, 1987,; C. S. Creaser, S. Crosland, F. Bawa, D. G. Cameron, H. R. Hudson, M. Pianka, O. O. Shode and J. F. Volckman, Proc. XV BMSS, 179 (, 1986.
   Google Scholar
• Fujiwara , H. and Wratten , S. J. 1987 . “ Application of Fast Atom Bombardment Mass Spectrometry to Polar Pesticides ” . In Applications of New Mass Spectrometry Techniques in Pesticide Chemistry 128 – 145 . New York : Wiley . ch. 10 in, ed. J. D. Rosen,pp.
   Google Scholar
• Rhyzhkov , V. L. , Kabachnik , M. I. , Tarasevich , L. M. , Medved' , T. Ya. , Zeitlenok , N. A. , Marchenko , N. K. , Vaghanova , V. A. , Ulanova , E. F. and Cheburkina , N. V. 1954 . Dokl. Akad. Nauk SSSR , 98 : 849
   PubMedGoogle Scholar
• Hilderbrand , R. L. , Curley-Joseph , J. , Lubansky , H. J. and Henderson , T. O. 1983 . “ Biology of Alkylphosphonic Acids: A Review of the Distribution, Metabolism, and Structure of Naturally Occurring Alkylphosphonic Acids ” . In Topics in Phosphorus Chemistry Edited by: Grayson , M. and Griffith , E. J. Vol. 11 , 297 – 338 . in“,”, eds., Interscience, New York,pp.
   Google Scholar
• Kafarski , P. and Mastalerz , P. 1984 . Aminophosphonates. Natural Occurrence, Biochemistry and Biological Properties Vol. 21 , Beiträge der Wirkstofforschung, Berlin, GDR,(.
   Google Scholar
• Giannousis , P. P. and Bartlett , P. 1987 . J. Med. Chem. , 30 : 1603
   PubMed Web of Science ®Google Scholar
• Engel , R. 1992 . “ The Use of C-P Analogue Compounds in the Regulation of Biological Processes ” . In ‘Handbook of Organophosphorus Compounds 559 – 600 . ch. 11 in, ed. R. Engel, Dekker, New York, N. Y.,pp.
   Google Scholar
• Coelln , R. and Luerssen , K. 1974 . Ger. Offen. 2 (to Bayer AG), 315 886(,Ger. Offen., 2 331 187 (1975); F. A. Hartman (to Procter and Gamble Co.), Ger. Offen., 2 424 135 (1974).
   Google Scholar
• 1992 . “ Aliphatic C—P Compounds as Herbicides ” . In Handbook of Organophosphorus Chemistry 739 – 805 . ch. 15 in, ed. R. Engel, Dekker, New York, N. Y.,pp.
   Google Scholar
• Baird , D. D. 1971 . Proc. Cent. Weed Control Conf. , 26 : 64 et al.;J. E. Franz (to Monsanto Co.) U. S. Patent 3 799 758 (1974).
   Google Scholar
• Schwerdtle , F. , Bieringer , H. and Finke , M. Z. 1981 . Pfl. Krankh. und Pfl. Schutz, Sonderheft IX 431 p.; W. Rupp, M. Finke, H. Bieringer and P. Langelueddeke (to Hoechst AG), Ger. Offen., 2 717 440 (1977).
   Google Scholar
• Tachibana , T. 1979 . et al.,Abstr. 5th Congr. Pestic. Chem., IVa, Abstract 19 Meiji Seika Kaisha Ltd.,Ger. Offen., 2 848 224(.
   Google Scholar
• Maier , L. 1983 . Phosphorus Sulfur , 14 : 295
   Web of Science ®Google Scholar
• Bayer , E. , Gugel , K. H. , Haegele , K. , Hagchmaier , H. , Jessipow , S. , Koenig , W. A. and Zaehner , H. 1972 . Helv. Chim. Acta. , 55 : 224
   PubMed Web of Science ®Google Scholar
• Niida , T. , Inoue , S. , Tsuruoka , T. , Shomura , T. , Kondo , Y. , Ogawa , Y. , Watanabe , H. , Kanahawa , S. , Watanabe , T. and Igarashi , H. 1973 . (to Meiji Confectionary Co., Ltd.)Ger. Offen. 2 236 599(.Chem. Abstr. 78, 109315t (1973) cf. Jap. Appln., 71 56 032 (1971).
   Google Scholar
• Kerst , A. F. and Douros , J. D. Jr. 1973 . (to The Gates Rubber Co.), U. S. Patent 3 764 677(.
   Google Scholar
• Maier , L. 1990 . Phosphorus, Sulfur, and Silicon , 53 : 43
   Web of Science ®Google Scholar
• Maier , L. and Diel , P. J. 1991 . Phosphorus, Sulfur, and Silicon , 62 : 15
   Web of Science ®Google Scholar
• Maier , L. and Diel , P. J. 1991 . Phosphorus, Sulfur, and Silicon , 57 : 57
   Web of Science ®Google Scholar
• Hepburn , D. R. and Hudson , H. R. 1976 . J. Chem. Soc., Perkin 1 , : 754
   Google Scholar
• Cameron , D. G. 1983 . Full details of the preparations of these intermediates are given elsewhere |cf.,Ph.D. thesis, CNAA, The Polytechnic of North London(|.
   Google Scholar
• We have found that the addition of a moderate, calculated excess of propylene oxide to a warm methanolic or ethanolic solution of the hydrochloride is the most effective procedure for ensuring clean precipitation of the free aminophosphonic acid. Addition “until the pH reaches 6,” as described previously,8 did not appear to be feasible; it led to the use of an unnecessarily large amount of propylene oxide and consequent difficulties in separation.
   Google Scholar
• Gancarz , R. and Wieczorck , J. S. 1977 . Synthesis , : 625
   Web of Science ®Google Scholar
• Lukszo , J. and Tyka , R. 1977 . Synthesis , : 239
   Google Scholar
• Kahovec , J. , Svec , F. and Marhol , M. 1978 . Org. Prep. Proceed. Int. , 10 : 285 .Chem. Abstr. 90, 104072z (1979).
   Web of Science ®Google Scholar
• Hori , T. , Itsaka , O. , Inoue , H. and Yamada , K. 1964 . J. Biochem. , 56 : 477
   PubMedGoogle Scholar
• Kosolapoff , G. M. 1947 . J. Am. Chem. Soc. , 69 : 2112
   Web of Science ®Google Scholar