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Structure-Activity Relationships of the Organophosphorus Anticholinesterase Agents

  • Chapter
Cholinesterases and Anticholinesterase Agents

Part of the book series: Handbook of Experimental Pharmacology ((HEP,volume 15))

Abstract

Organic chemists have the habit of tasting new compounds. Useful drugs like local anaesthetics have been discovered in this way. On the other hand, it is amazing that so few scientists have met a premature death as a result. It is remarkable, for example, that the French nobleman and organic chemist Philippe de Clermont did not succumb to tetraethyl pyrophosphate (TEPP) poisoning in 1854. If this had happened, the toxicity of the anticholinesterase (anti-ChE) agents of the organophosphorus type would have been discovered much earlier than it actually was.

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References

  1. Aaron, H. S., H. O. Michel, B. Wrrren and J. I. Miller: Stereochemistry of asymmetric phosphorus compounds. II. Stereospecificity in the irreversible inactivation of cholinesterases by the enantiomorphos of an organophosphorus inhibitor. J. Amer. chem. Soc. 80, 456–458 (1958).

    Article  CAS  Google Scholar 

  2. Adams, D. H., and V. P. Whittaker: The cholinesterase of human blood. II. The forces acting between enzyme and substrate. Biochim. biophys. Acta 4, 543–558 (1950).

    CAS  Google Scholar 

  3. Adebahr, G.: Nierenveränderungen bei der E 605-Vergiftung des Menschen. Arch. Toxikol. 18, 107–120 (1960).

    Article  CAS  Google Scholar 

  4. Adie, P. A.: The effect of the sarinase levels of liver on the survival of rabbits injected with sarin. Canad. J. Biochem. 34, 654–659 (1956).

    Article  CAS  PubMed  Google Scholar 

  5. Adie, P. A.: The purification of sarinase from bovine plasma. Canad. J. Biochem. 34, 1091–1094 (1956).

    Article  CAS  PubMed  Google Scholar 

  6. Adie, P. A.: Studies on the enzymatic hydrolysis of sarin and tabun. Canad. J. Biochem. 36, 15–20 (1958).

    Article  CAS  PubMed  Google Scholar 

  7. Adie,P.A.,S.C.K. Hoskin and G. S. Trick: Kinetics of the enzymatic hydrolysis of sarin. Canad. J. Biochem. 34, 80–82 (1956).

    Article  CAS  PubMed  Google Scholar 

  8. Adie, P. A., and J. Tuba: The intracellular localization of liver and kidney sarinase. Canad. J. Biochem. 36, 21–24 (1958).

    Article  CAS  PubMed  Google Scholar 

  9. Aldridge, W. N.: Some properties of specific cholinesterase with particular reference to the mechanism of inhibition by diethyl-p-nitrophenyl thiophosphate (E 605) and analogues. Biochem. J. 46, 451–459 (1950).

    CAS  PubMed  Google Scholar 

  10. Aldridge, W. N.: The differentiation of true and pseudo cholinesterase by organ-phosphorus compounds. Biochem. J. 53, 62–67 (1953).

    CAS  PubMed  Google Scholar 

  11. Aldridge, W. N., and J. M. Barnes: Some problems in assessing the toxicity of the “Organophosphorus” insecticides towards mammals. Nature (tond.) 169, 345–352 (1952).

    Article  CAS  Google Scholar 

  12. Aldridge, W. N., and A. N. Davison: The inhibition of erythrocyte cholinesterase by tri-esters of phosphoric acid. 1. Diethyl p-nitrophenyl phosphate (E 600) and analogues. Biochem. J. 51, 62–70 (1952).

    CAS  PubMed  Google Scholar 

  13. Aldridge, W. N., and A. N. Davison:The inhibition of erythrocyte cholinesterase by tri-esters of phosphoric acid. 2. Diethyl p-nitrophenyl thionphosphate (E 605) and analogues. Biochem. J. 52, 663–671 (1952).

    CAS  PubMed  Google Scholar 

  14. Aldridge, W. N., and A. N. Davison: The mechanism of inhibition of cholinesterases by organophosphorus compounds. Biochem. J. 55, 763–766 (1953).

    CAS  PubMed  Google Scholar 

  15. American Cyanamid Co. U.S. Pat. 2, 664, 437.

    Google Scholar 

  16. Anderson, C. A., J. M. Adams and D. Macdougall: Photofluorimetric method for determination of Co-Ral residues in animal tissues. J. Agric. Food Chem. 7, 256–259 (1959).

    Article  CAS  Google Scholar 

  17. Andrews, K. J. M., F. R. Atherton, F. Bergel and A. L. Morrison: The synthesis of neurotropic and musculotropic stimulators and inhibitors. Part V. Derivatives of amino-phenyl phosphates as anticholinesterases. J. chem. Soc. 1952, 780–784.

    Google Scholar 

  18. Andrews, K. J. M., F. R. Atherton, F. Bergel and A. L. Morrison: Hydroxypyridine and hydroxyquinoline phosphates as anticholinesterases. J. chem. Soc. 1954, 1638–1640.

    Google Scholar 

  19. Arbusow, A. E.: Über die Struktur der phosphorigen Säure und ihre Derivate. IV. Isomerisation und Übergang der Verbindungen des dreiwertigen Phosphors in solche des fünfwertigen. Chem. Zbl. 2, 1640 (1906).

    Google Scholar 

  20. Arbusow, A. E.: The Kazan school of chemists. Uspekhi Khim 9, 1378–1394 (1940).

    Google Scholar 

  21. Arbusow, A. E., u. B A Arbusow: Über die Ester der pyrophosphorigen, der Unterphosphor-und der Pyrophosphorsäure. J. prakt. Chem. 238, 103–132 (1931).

    Article  Google Scholar 

  22. Arthur, B. W., and J. E. Casida: Metabolism and selectivity of 0,0-dimethyl 2,2,2trichloro-1-hydroxyethyl phosphonate and its acetyl and vinyl derivatives. J. Agric. Food Chem. 5, 186–191 (1957).

    Article  CAS  Google Scholar 

  23. Arthur, B. W., and J. E. Casida: Biological and chemical oxidation of tetramethyl phosphordiamidic fluoride (dimefox). J. econ. Ent. 51, 49–56 (1958).

    CAS  Google Scholar 

  24. Arthur, B. W., and J. E. Casida: Pesticide toxicity. Biological activity of several 0,0-dialkyl alpha-acyloxyethyl phosphonates. J. Agric. Food Chem. 6, 360–365 (1958).

    Article  CAS  Google Scholar 

  25. Arthur, B. W., and J. E. Casida: Biological activity and metabolism of Hercules AC-528 components in rats and cockroaches. J. econ. Ent. 52, 20–27 (1959).

    CAS  Google Scholar 

  26. Augustinsson, K.-B.: Mintacol (diethyl p-nitrophenyl phosphate). Svensk farm. Tidskr. 57, 261–267 (1953).

    CAS  Google Scholar 

  27. Augustinsson, K.-B.: Biochemical studies with Tabun and allied compounds. Ark. Kemi 6, 331–350 (1953).

    CAS  Google Scholar 

  28. Augustinsson, K.-B.: The chemical determination of parathion and its application to biological material. Acta agric. Stand. 7, 165–189 (1957).

    CAS  Google Scholar 

  29. Augustinsson, K.-B., and G. Joxssox: Biochemical studies on the degradation products of diazinone. Experientia (Basel) 13, 438–443 (1957).

    Article  CAS  Google Scholar 

  30. K.-B.Augustinsson, and D. Nachmansohn: Studies on cholinesterase. VI. Kinetics of the inhibition of acetylcholine esterase. J. biol. Chem. 179, 543–559 (1949).

    Google Scholar 

  31. K.-B.Augustinsson, and D. Nachmansohn: Distinction between acetylcholine-esterase and other choline ester-splitting enzymes. Science 110, 98–99 (1949).

    Google Scholar 

  32. Austin, L., and W. K. Berry: Two selective inhibitors of cholinesterase. Biochem. J. 54, 695–700 (1953).

    CAS  PubMed  Google Scholar 

  33. Bachmann, F: Phosphamidon, ein neuer Phosphorsäureester mit systemischer Wirkung. Summary of Communications, IVth International Congress of Crop Protection 1957, p. 164.

    Google Scholar 

  34. Bagdon, R. F., and K. P. Dubois: Pharmacologic effects of chlorthion, malathion and tetrapropyl dithiono pyrophosphate in mammals. Arch. int. Pharmacodyn. 103, 192–199 (1955).

    CAS  Google Scholar 

  35. Banister, J., and V. P. Wihttaxer: Pharmacological activity of the carbon analogue of acetylcholine. Nature (Lond.) 167, 605 (1951).

    Article  CAS  Google Scholar 

  36. Barnes, J. M., and J. I. Duff: The role of cholinesterase at the myoneural junction. Brit. J. Pharmacol. 8, 334–339 (1953).

    CAS  PubMed  Google Scholar 

  37. Barnes, J. M., and J. I. Duff:.Acetylcholine production in animals poisoned by diethyl-p-nitrophenyl phosphate (paraoxon). Brit. J. Pharmacol. 9, 153–158 (1954).

    CAS  PubMed  Google Scholar 

  38. W. F. Barthel, B. H. Alexander, P. A. Giang and S. A. Hall: Insecticidal phosphates obtained by a new rearrangement reaction. J. Amer. chem. Soc. 77, 2424–2427 (1955).

    Article  CAS  Google Scholar 

  39. W. F. Barthel, P. A. Giang and S. A. Hall: Dialkyl a-hydroxyphosphonates derived from chloral. J. Amer. chem. Soc. 76, 4186–4187 (1954).

    Article  CAS  Google Scholar 

  40. Benjamini, E., R. L. Metcalf and T. R. Fukuto: The chemistry and mode of action of the insecticide 0,0-diethyl 0,-p-methylsulfinylphenyl phosphorothionate and its analogues. J. econ. Ent. 52, 94–98 (1959).

    CAS  Google Scholar 

  41. Benjamini, E., R. L. Metcalf and T. R. Fukuto: Contact and systemic insecticidal properties of 0,0-diethyl O-p-methylsulfinylphenyl phosphorothionate and its analogues. J. econ. Ent. 52, 99–102 (1959).

    CAS  Google Scholar 

  42. Berg; S., E. Kuchinke u. K. Fischer: Zur Kenntnis der Vergiftung mit dem Schädlingsbekämpfungsmittel Potasan G. Arch. Toxikol. 16, 105–117 (1956).

    Google Scholar 

  43. Berry, W. K.: Biochemical mechanism after poisoning with anticholinesterase. Proc. roy. Soc. Med. 46, 801–802 (1953).

    CAS  Google Scholar 

  44. Bockel, P.: Vergiftung mit einem Phosphorsäureesterpräparat der Diazinon-Gruppe „Basudin“. Dtsch. med. Wschr. 82, 1230–1231 (1957).

    Article  CAS  Google Scholar 

  45. Bocquet, J. R.: Contribution à l’étude de la synthèse des halogenophosphates d’alkyle radioactifs et de l’inhibition de la cholinestérase par ces toxiques organophosphones. Les Editions Acta med. Belg. Bruxelles 1956.

    Google Scholar 

  46. Bodansity, O.: Contributions of medical research in chemical warfare to medicine. Science 102, 517–521 (1945).

    Article  Google Scholar 

  47. Bombinski, T. J., and K. P. Dubois: Toxicity and mechanism of action of di-syston. A. M. A. Arch. industr. Hlth 17, 192–199 (1958).

    CAS  Google Scholar 

  48. Bonnaud: L’arme chimique est-elle périmée? Protar 14, 113–115 (1948).

    Google Scholar 

  49. Bourret, J., L. Derobert u. M. Gueniot: Intoxications volontaires par insecticides organo-phosphorés (Parathion). Aim Méd. lég. 38, 160–164 (1958).

    CAS  Google Scholar 

  50. Bowman, J. S.: Further studies on the metabolism of Thimet by plants, insects, and mammals. J. econ. Ent. 51, 838–843 (1958).

    CAS  Google Scholar 

  51. Bowman, J. S., and J. E. CASIDA: Metabolism of the systemic insecticide 0,0-diethyl S-ethylthiomethyl phosphorodithioate (Thimet) in plants. J. Agric. Food Chem. 5, 192–197 (1957).

    Article  CAS  Google Scholar 

  52. Boyd, G. R.: Determination of residues of 0–2,4-dichlorophenyl 0,0-diethyl phosphorothioate (V-C 13 Nemacide) by cholinesterase inhibition. J. Agric. Food Chem. 7, 615–617 (1959).

    Article  CAS  Google Scholar 

  53. Brauer, R. W.: Inhibition of the cholinesterase activity of human blood plasma and erythrocyte stromata by alkylated phosphorus compounds. J. Pharmacol. 92, 162–172 (1948).

    CAS  Google Scholar 

  54. Brit. Pat. 688, 760.

    Google Scholar 

  55. Bruce, R. B., J. W. Howard and J. R. Elsea: Toxicity of 0,0-diethyl O-(2-isopropyl-6methyl-4-pyrimidyl) phosphorothioate (Diazinon). J. Agric. Food Chem. 3, 1017–1021 (1955).

    Article  CAS  Google Scholar 

  56. Burgen, A. S. V.: The mechanism of action of anticholinesterase drugs. Brit. J. Pharmacol. 4, 219–228 (1949).

    CAS  PubMed  Google Scholar 

  57. Burgen, A. S. V., and L. M. Chipman: The location of cholinesterase in the central nervous system. Quart. J. exp. Physiol. 37, 61–74 (1952).

    CAS  PubMed  Google Scholar 

  58. Burgen, A. S. V., and F. Hobbiger: The inhibition of cholinesterases by alkylphosphates and alkyl-phenolphosphates. Brit. J. Pharmacol. 6, 593–605 (1951).

    CAS  PubMed  Google Scholar 

  59. Burgen, A. S. V. C. A. Keele and D. Slome: Pharmacological actions of tetraethylpyrophosphate and hexaethyltetraphosphate. J. Pharmacol. 96, 396–409 (1949).

    CAS  Google Scholar 

  60. de Candole, C. A.: Successful use of pressor drugs in paraoxon poisoning. Rev. canad. Biol. 15, No. 3 (1956).

    Google Scholar 

  61. W. W. Douglas, C. Lovait Evans, R. Holmes, K. E. V. Spencer, R. W. Torrance and K. M. Wrrson: The failure of respiration in death by anticholinesterase poisoning. Brit. J. Pharmacol. 8, 466–475 (1953).

    PubMed  Google Scholar 

  62. W. W. Douglas, and M. K. Mcphan,: Sarin and paraoxon antagonism in different species. Canad. J. Biochem. 35, 1071–1083 (1957).

    Article  Google Scholar 

  63. Casida, J. E.: Metabolism of organophosphorus insecticides in relation to their anti-esterase activity, stability, and residual properties. J. Agric. Food Chem. 4, 772–785 (1956).

    Article  CAS  Google Scholar 

  64. J. E. Casida, T. C. Allen and M. A. Stahmlnn: Mammalian conversion of octamethyl-pyrophosphoramide to a toxic phosphoramide-N-oxide. J. biol. Chem. 210, 607–616 (1954).

    CAS  PubMed  Google Scholar 

  65. J. E. Casida, R. K. Chapman, M. A. Starmann and T. C. Allen: Metabolism of schradan by plants and insects to a toxic phosphoramide oxide. J. econ. Ent. 47, 64–71 (1954).

    CAS  Google Scholar 

  66. Casida, J., P. Gatterdam, L. Getzin and R. Chapman: Residual properties of the systemic insecticide 0,0-dimethyl 1-carbomethoxy-l-propen-2-y1 phosphate. J. Agric. Food Chem. 4, 236–243 (1956).

    Article  CAS  Google Scholar 

  67. Cassaday, J. T.: U.S. Pat. 2,578,652 v. 2. 3. 1950.

    Google Scholar 

  68. Chapman, N. B., and B. C. Saunders: Esters containing phosphorus. Part VI. Preparation of esters of fluorophosphonic acid by means of phosphorus oxydichlorofluoride. J. Chem. Soc. 1948, 1010–1014.

    Google Scholar 

  69. Cheng, K. K.: A technique for total hepatectomy in the rat and its effect on toxicity of octamethyl pyrophosphoramide. Brit. J. exp. Path. 32, 444 447 (1951).

    Google Scholar 

  70. Chennells, M., W. F. Floyd and S. Wright: Action of condensed alkyl phosphates on the nerve-muscle preparation and the central nervous system of the cat. J. Physiol. 108, 375–397 (1949).

    CAS  PubMed  Google Scholar 

  71. Chouteau, J., J. P. Vigne, A. Karamanian et R. L. Tabau: Sur l’activité antiestérasique de certain esters organophosphoriques complexes à propriétés insecticides. C. R. Soc. Biol. (Paris) 150, 1773–1777 (1956).

    CAS  Google Scholar 

  72. CIBA/Schweiz, DBP. 845,226.

    Google Scholar 

  73. de Clermont, PH.: Note sur la préparation de quelques éthers. (Séance du lundi 14 août 1854). C. R. 39, 338–340 (1854).

    Google Scholar 

  74. de Clermont, PH.: Mémoire sur les éthers phosphoriques. Ann. Chim. Phys. 44, 330–336 (1855).

    Google Scholar 

  75. Coates, H.: Chemistry of phosphorus insecticides. Ann. appl. Biol. 36, 156–159 (1949).

    CAS  PubMed  Google Scholar 

  76. Coe, D. G., H. Hurtig, B. J. Perry and E. S. Sherlock: Some new organophosphorus compounds with insecticidal properties. J. Agric. Food Chem. 7, 251–255 (1959).

    Article  CAS  Google Scholar 

  77. Cohen, J. A., P. J. Warringa and I. Indorf: Relationship between the pharmacological action of neuromuscular drugs and their capacity to inhibit esterases. Acta physiol. pharm. néerl. 4, 187–200 (1955).

    CAS  Google Scholar 

  78. Cohen, J. A., and C. H. Posthumus: The mechanism of action of anticholinesterases. III. The action of anticholinesterases on the phrenic nerve-diaphragm preparation of the rat. Acta physiol. pharm. néerl. 5, 385–397 (1957).

    CAS  Google Scholar 

  79. Cohen, J. A., and C. H. Posthumus: The mechanism of action of anticholinesterases. Acta physiol. pharm. néerl. 4, 17–36 (1958).

    Google Scholar 

  80. Collomp: Les Triions. Bull. d’Information technique et Scientifique. Numéro 23/G, Janvier 1949. Ministère de la Guerre. Section technique de l’armée.

    Google Scholar 

  81. Conley, B. E.: Antagonism of lethal action of parathion by 3-pyridine acetohydroxamic acid methyl iodide. Fed. Proc. 17, 360 (1958).

    Google Scholar 

  82. Cook, H. G., J. D. Ilett, B. C. Saunders, G. J. Stacey, H. G. Watson, I. G. E. Wilding and S. J. Woodcock: Esters containing phosphorus. Part IX. J. chem. Soc. 1949, 2921–2927.

    Google Scholar 

  83. B. C. Saunders and F. E. Smrrh: Esters containing phosphorus. Part VIII. Structural requirements for high toxicity and miotic action of esters of fluorophosphonic acid. J. chem. Soc. 1949, 635–638.

    Google Scholar 

  84. J. W.Cook, J. R. Blake and M. W. Williams: The enzymic hydrolysis of malathion and its inhibition by EPN and other organic phosphorus compounds. J. Ass. off. agric. Chem. Wash. 40, 664–665 (1957).

    CAS  Google Scholar 

  85. J. W., Cook, J. R. Blake G. YIP and M. Williams • Malathionase. I. Activity and inhibition. II. Identity of a malathion metabolite. J. Ass. agric. Chem. 41, 399–411 (1958).

    Google Scholar 

  86. Corey, R. A., S. C. Dorman, W. E. Hall, L. C. Glover and R. R. Whetstone: Diethyl 2-chlorovinyl phosphate and di-methyl 1-carbo-methoxy-l-propen-2-y1 phosphate. Science 118, 28–29 (1953).

    Article  CAS  PubMed  Google Scholar 

  87. Craig, F. N., P. D. Bales and H. M. Frankel: Lethality of sarin in a warm environment. J. Pharmacol. 127, 35–38 (1959).

    CAS  Google Scholar 

  88. Dauterman, W. C., J. E. Casida, J. B. Knaas and T. Kowalczyk: Bovine metabolism of organophosphorus insecticides. Metabolism and residues associated with oral administration of dimethoate to rats and three lactating cows. J. Agric. Food Chem. 7, 188–193 (1959).

    Article  CAS  Google Scholar 

  89. Davies, D. R.: Cholinesterases and the mode of action of some anticholinesterases. J. Pharm. (Lond.) 6, 1–26 (1954).

    Article  Google Scholar 

  90. Davison, A. N.: Return of cholinesterase activity in the rat after inhibition by organo-phosphorus compounds. Biochem. J. 54, 583–590 (1953).

    CAS  PubMed  Google Scholar 

  91. de Burgh Daly, M.: The effects of anticholinesterases on the bronchioles and pulmonary blood vessels in isolated perfused lungs of the dog. Brit. J. Pharmacol. 12, 504–512 (1957).

    CAS  Google Scholar 

  92. de Burgh Daly, M.: The cardiovascular effects of anticholinesterases in the dog with special reference to haemodynamic changes in the pulmonary circulation. J. Physiol 139, 250–272 (1957).

    Google Scholar 

  93. de Burgh Daly, M. and P. G. Wright: The effects of anticholinesterases upon pulmonary vascular resistance in the dog. J. Physiol. 139, 273–293 (1957).

    Google Scholar 

  94. de Burgh Daly, M. and P. G. Wright: The effects of anticholinesterases upon peripheral vascular resistance in the dog. J. Physiol. 133, 475–497 (1956).

    CAS  PubMed  Google Scholar 

  95. Deichmann, W. B., P. Brown and C. Downing: Unusual protective action of a new emulsifier for the handling of organic phosphates. Science 116, 221 (1952).

    Article  CAS  PubMed  Google Scholar 

  96. Deichmann, W. B., and K. Lampe Dipterex: Its pharmacologic action and an appraisal of the hazard associated with its use. Univ. Miami School Med. Bull. 9, 7–12 (1955).

    Google Scholar 

  97. W. B. W. Deichmann, Pugliese and J. Cassidy: Effects of dimethyl and diethyl paranitrophenyl thiophosphate on experimental animals. A.M.A. Arch. industr. Hyg. 5, 44–51 (1952).

    CAS  Google Scholar 

  98. W. B. W. Deichmann, and R. Rasoczy: Buscopan in treatment of experimental poisoning by parathion, methyl parathion and systox. A.M.A. Arch. industr. Hyg. 7, 152–156 (1953).

    CAS  Google Scholar 

  99. W. B. W. Deichmann, and R. Rasoczy: Toxicity and mechanism of action of Systox. A.M.A. Arch. industr. Hlth 11, 324–331 (1955).

    CAS  Google Scholar 

  100. Dickinson, B. C.: Ethion, a promising new acaricide and insecticide. J. econ. Ent. 51, 354–357 (1958).

    CAS  Google Scholar 

  101. Die, Jvan: Inhibition of serum cholinesterase by O,0-dimethyl-2,2,2-trichloro-1-hydroxyethyl phosphonate and 0,0-dimethyl 0–2,2-dichlorovinyl phosphate. Koninkl. Ned. Akad. Wetenschap Proc. Ser. B 60, 227–233 (1957).

    Google Scholar 

  102. Diggle, W. M., and J. C. Gage: Cholinesterase inhibition in vitro by 0,0-diethyl O-p-nitrophenyl thiophosphate (Parathion, E 605). Biochem. J. 49, 491–494 (1951).

    CAS  PubMed  Google Scholar 

  103. Dirnhuber, P., and H. Cullumbine: The effect of anticholinesterase agents on the rats blood pressure. Brit. J. Pharmacol. 10, 12–15 (1955).

    CAS  PubMed  Google Scholar 

  104. di Stefano, V., L. Hurwitz, W. F. Neuman and H. C. Hodge: Coramine (Nikethamide) as an adjuvant to atropine in treatment of poisoning by EPN (ethyl p-nitrophenyl thionobenzene-phosphonate. Proc. Soc. exp. Biol. (N. Y.) 78, 712–713 (1951).

    Article  Google Scholar 

  105. Diveley, W. R., A. H. Haubein, A. D. Lohr, and P. B. Moseley: Two new organo-phosphorus derivatives of p-dioxane with excellent insecticidal and acaricidal activity. J. Amer. chem. Soc. 81, 139–144 (1959).

    Article  Google Scholar 

  106. Diveley, W. R., and A. D. Loan: 2,3-p-dioxanedithiol S,S-bis(0,0-dialkyl phosphorodithioate). U.S. Patent No. 2,725–328, Nov. 20, 1955.

    Google Scholar 

  107. Douglas, W. W., and P. B. C. Mairnews: Acute tetraethylpyrophosphate poisoning in cats and its modification by atropine or hyoscine. J. Physiol. (Lond.) 116, 202–218 (1952).

    CAS  Google Scholar 

  108. Dounn, J., and K. P. Dubois: Toxicity and anticholinesterase action of tetra-n-propyl dithionopyrophosphate. J. Pharmacol. 106, 382 (1952).

    Google Scholar 

  109. Dubois, K. P., and J. M. Coon: Toxicology of organic phosphorus-containing insecticides to mammals. Arch. industr. Hyg. 6, 9–13 (1952).

    CAS  Google Scholar 

  110. Dubois, K. P., and G. J. Cotter: Studies on the toxicity and mechanism of action of dipterex. A.M.A. Arch. industr. Hlth 11, 53–60 (1955).

    CAS  Google Scholar 

  111. K. P.Dubois, J. Douu and J. M. Coon: Studies on the toxicity and pharmacological action of octamethyl pyrophosphoramide (OMPA; Pestox III). J. Pharmacol. 99, 376–393 (1950).

    Google Scholar 

  112. K. P.Dubois, J. Douu and J. M. Coon:The cholinergic action of octamethyl pyrophosphoramide (OMPA). J. Pharmacol. 98, 6–7 (1950).

    Google Scholar 

  113. K. P.Dubois, J. Douu,J. Deroin and O. K. Cummings: Studies on the toxicity and mechanism of action of some new insecticidal thionophosphates. A.M.A. Arch. industr. Hyg. 8, 350 to 358 (1953).

    Google Scholar 

  114. K. P.Dubois, J. Douu,J. Deroin and J. M. Coon: Studies on the toxicity and mechanism of action of p-nitrophenyl diethyl thionophosphate (parathion). J. Pharmacol. 95, 79–91 (1949).

    Google Scholar 

  115. K. P.Dubois S. D. Murphy and D. R. Thursh JR.: Toxicity and mechanism of action of some metabolites of Systox. A.M.A. Arch. industr. Hlth 13, 606–612 (1956).

    Google Scholar 

  116. Dunn, C. L.: Determination of 2,3-p-dioxanedithiol S,S-bis(O,0-diethyl phosphorodithioate). J. Agric. Food Chem. 6, 203–209 (1958).

    Article  CAS  Google Scholar 

  117. Durham, W. F.: The toxicity of chemicals used in mosquito control. Proc. of the Forty-fourth Ann. Meeting of the New Jersey Mosquito Extermination Ass. Held at Atlantic City March 13, 14 and 15, 1957, pp. 155–160.

    Google Scholar 

  118. W. F. Durham, T. B. Gaines, R. H. Mcgauley, V. A. Sedlax, A. M. Mattson and W. J. Hayes: Studies on the toxicity of O,O-dimethyl-2,2-dichlorovinyl phosphate (DDVP). A.M.A. Arch. industr. Hlth 15, 340–349 (1957).

    CAS  Google Scholar 

  119. W. F. Durham W. J. Hayes ja.,and A. M. Mattson: Toxicological studies of O,O-dimethyl-2,2-dichiorovinyl phosphate (DDVP) in tobacco warehouses. A.M.A. Arch. industr. Hlth 20, 202–210 (1959).

    Google Scholar 

  120. Dybing, O., and E. Sognen: Hyperglycaemia in rats after diazinon and other cholinesterase inhibitors. Acta pharmacol. 14, 231–235 (1958).

    Article  CAS  Google Scholar 

  121. Edson, E. F.: Threshold effects of organic phosphorus insecticides in the diet of the rat, pig and humans Summary of communications. IVth International Congress of Crop Protection 1957, 221.

    Google Scholar 

  122. Enander, I.: Experiments with methyl-fluoro-phosphorylcholine-inhibited cholinesterase. Acta Chem. scand. 12, 780–781 (1958).

    Article  CAS  Google Scholar 

  123. W. D.Erdmann,, H. D. Kempe u. W. Lühning: Über die Wirkung von Esteraseblockern (E 605, Eserin und Prostigmin) auf das Atemzentrum von Katze und Hund. Naunyn-Schmiedeberg’s Arch. exp. Path. Pharmak. 225, 359–368 (1955).

    Google Scholar 

  124. W. D.Erdmann, u. L. Lendle: Vergiftungen mit esteraseblockierenden Insecticiden aus der Gruppe der organischen Phosphorsaure-Ester (E 605 und Verwandte). Ergebn. inn. Med. Kinderheilk., new ser. 10, 104–184 (1958).

    Google Scholar 

  125. W. D.Erdmann, u. F. Saxai: Analyse der unspezifisch lähmenden Wirkung einiger Alkylphosphate (E 600 und E 605). Naunyn-Schmiedeberg’s Arch. exp. Path. Pharmakol. 236, 205–207 (1959).

    Google Scholar 

  126. Fiszer, B., J. Michalski and J. Wieczobkowski: Roczniki Chem. 27, 482 (1953).

    CAS  Google Scholar 

  127. Fletcher, J. H., J. C. Hamilton, I. Hechenbleikner, E. J. Hoegberg, B. J. Sertl and J. T. Cassaday: Preparation of 0,0-diethyl O-p-nitrophenyl thiophosphate (Parathion). J. Amer. chem. Soc. 70, 3943–3944 (1948).

    Google Scholar 

  128. Fournel, J.: Action antidote de l’iodométhylate de l’a-pyridylaldoxime vis-à-vis des intoxications expérimentales provoquées par les insecticides organophosphorés. C. R. Soc. Biol. (Paris) 151, 1373–1377 (1958).

    Google Scholar 

  129. J. Fournel, J. Desmoras, P. Dubost, R. Ducrot et. L. JuLou: Toxicité d’un nouvel ester phosphorique à action endothérapique: le 7175 R.P. ou Endothion. Summary of communications. IVth International Congress of Crop Protection 1957, 221–222.

    Google Scholar 

  130. Frawley, J. P., and H. N. Fuyat: Effect of low dietary levels of Parathion and Systox on blood cholinesterase of dogs. J. Agric. Food Chem. 5, 346–348 (1957).

    Article  CAS  Google Scholar 

  131. Frawley, J. P., H. N. Fuyat E. C. H.gan, J. R. Blake and O. G. Fitzhugh: Marked potentiation in mammalian toxicity from simultaneous administration of two anticholinesterase compounds. J. Pharmacol. 121, 96–106 (1957).

    CAS  Google Scholar 

  132. J. P. Frawley, E. C. Hagan and O. G. Fitzhugh: A comparative pharmacological and toxicological study of organic phosphate-anticholinesterase compounds. J. Pharmacol. 105, 156–165 (1952).

    CAS  Google Scholar 

  133. Freak, D. E. H.: Chemistry of the pesticides, p. 82. New York: D. van Nostrand Co. Inc. 1955.

    Google Scholar 

  134. Fredriksson, T.: Pharmacological properties of methylfluorophosphorylcholines. Two synthetic cholinergie drugs. Arch. int. Pharmacodyn. 113, 101–113 (1957).

    CAS  Google Scholar 

  135. Fredriksson, T. Studies on the percutaneous absorption of sarin and two allied organophosphorus cholinesterase inhibitors. Acta derm.-venereol. (Stockh.) 38, 1–83, Suppl. 41 (1958).

    Google Scholar 

  136. Fredriksson, T. Further studies on fluoro-phosphorylcholines. Pharmacological properties of two new analogues. Arch. in Pharmacodyn. 115, 474–482 (1958).

    Google Scholar 

  137. Fredriksson, T. C.-H. Hansson and B. Holmstedt: Effects of sarin in the anaesthetized and un-anaesthetized dog following inhalation, percutaneous absorption and intravenous infusion. Arch. int. Pharmacodyn. 126, 288–302 (1960).

    CAS  Google Scholar 

  138. Fredriksson, T., and G. Trebling: Reversal of effects on the rat nerve-diaphragm preparation produced by methylfluorophosphorylcholines. Biochem. Pharmacol. 2, 63–67 (1959).

    Article  CAS  Google Scholar 

  139. Fredriksson, T., and G. Trebling: Demonstration of direct cholinergic receptor effects of methylfluorophosphorylcholines. Biochem. Pharmacol. 2, 286–289 (1959).

    Article  CAS  PubMed  Google Scholar 

  140. Fredriksson, T., and G. Trebling: Inhibition of cholinesterase with methylfluorophosphoryleholiin and — carbocholine, spontaneous return of activity. J. Biochem. Pharmacol. 3, 184–189 (1960).

    Article  CAS  Google Scholar 

  141. French patent 1096341.

    Google Scholar 

  142. Fuxuhar, A.: Parathion poisoning. III. Effect of sulfhydryl compounds and 2-pyridine aldoxime methiodide on parathion poisoning. Okayama Igakkai Zasshi 69, 945–958 (1957).

    Google Scholar 

  143. Fuxuto, T. R., and R. L. Metcalf: Manuscript submitted to J. Agric. Food Chem. 1954. See Agr. Chem. 9, 130 (1954).

    Google Scholar 

  144. Fuxuto, T. R., and R. L. Metcalf: Structure and insecticidal activity of some diethyl substituted phenyl phosphates. J. Agric. Food Chem. 4, 930–935 (1956).

    Article  Google Scholar 

  145. Fuxuto, T. R., and R. L. Metcalf R. B. March and M. Maxon: A water soluble systemic insecticide 0,0-diethyl S-2-ethylmercaptoethyl phosphorothiolate methosulfate. J. Amer. chem. Soc. 77, 3670 to 3671 (1955).

    Google Scholar 

  146. Fuxuto, T. R., and R. L. Metcalf R. B. March and M. Maxon:Chemical behavior of Systox isomers in biological systems. J. econ. Ent. 48, 347–354 (1955).

    Google Scholar 

  147. Fuxuto, T. R., and E. M. Stafford: The isomerization of 0,0-diethyl 0–2-diethylaminoethyl phosphoro thionate. J. Amer. chem. Soc. 79, 6083–6085 (1957).

    Article  Google Scholar 

  148. J. P. Wolf III, R. L. Metcalf and R. B. March: Identification of the sulfone plant metabolite of the thiono isomer of Systox. J. econ. Ent. 50, 399–401 (1957).

    Google Scholar 

  149. Gage, J. C.: A cholinesterase inhibitor derived from 0,0-diethyl O-p-nitrophenyl thiophosphate in vivo. Biochem. J. 54, 426–430 (1953).

    CAS  PubMed  Google Scholar 

  150. Gage, J. C., and J. Payton: The action of diethyl-p-nitrophenyl thiophosphate (Parathion, E 605) in vivo. Résumé des communications IP Congr. int. Biochimie, Paris, 1952.

    Google Scholar 

  151. Gardiner, J. E., and B. A. Kum: I The mammalian metabolism of bis(dimethylamino)phosphorous anhydride (Schradan). Biochem. J. 51, 78–85 (1952).

    CAS  PubMed  Google Scholar 

  152. Gasser, R.: Expériences dans la lutte contre les araignées rouges avec de nouveaux acaricides. III. Int. Congr. Phytopharmacy, Paris, 1952, p. 51.

    Google Scholar 

  153. Gasser, R.: Über ein nues Insektizid mit breitem Wirkungsspektrum. Z. Naturforsch. 8 B, 225 to 232 (1953).

    Google Scholar 

  154. Gatterdam, P. E., J. E. Casida and D. W. Stoutamire: Relation of structure to stability, antiesterase activity and toxicity with substituted-vinyl phosphate insecticides. J. econ. Ent. 52, 270–276 (1959).

    CAS  Google Scholar 

  155. Gnosh, R.: Phosphorodithioates. Brit. Pat. 783,281, Sept. 18, 1957.

    Google Scholar 

  156. Gnosh, R., and J. F. Newman: A new group of organophosphorus pesticides. Chem. and Ind. 1955, p. 118, Jan. 1929.

    Google Scholar 

  157. Giang, P. A.: A bibliography of systemic insecticides. U.S. Dept. of Agriculture, Agricultural Research Service Ent. Research Branch E-874, 1954.

    Google Scholar 

  158. Giang, P. A., and R. L. Caswell: Polarographic determination of 0,0-dimethyl 2,2,2-tri-chloro1-hydroxy-ethylphosphonate (Bayer L 13/59). J. Agric. Food Chem. 5, 753–754 (1957).

    Article  CAS  Google Scholar 

  159. Gilman, A.: The effects of drugs on nerve activity. Ann. N. Y. Acad. Sci. 47, 549–558 (1946).

    Article  CAS  Google Scholar 

  160. Goldman, H., and M. Teitel: Malathion poisoning in a 34 month-old child following accidental ingestion. J. Pediat. 52, 76–81 (1958).

    Article  CAS  PubMed  Google Scholar 

  161. Gothelf, B., A. G. Karczmar and K. Blachut: Interaction of bisquaternary and phosphonate anticholinesterases. Fed. Proc. 17, 372 (1958).

    Google Scholar 

  162. Green, A. L.: The kinetic basis of organophosphate poisoning and its treatment. Biochem. Pharmacol. 1, 115–128 (1958).

    Article  Google Scholar 

  163. Grob, D.: The manifestations and treatment of poisoning due to nerve gas and other organic phosphate anticholinesterase compounds. A.M.A. Arch. intern. Med. 98, 221–239 (1956).

    Article  CAS  Google Scholar 

  164. Grob, D., and A. M. Harvey: The effects and treatment of nerve gas poisoning. Amer. J. Med. 14, 52–63 (1953).

    Article  CAS  PubMed  Google Scholar 

  165. Grob, D., and A. M. Harvey: Effects in man of the anticholinesterase compound sann (isopropyl methyl phosphonofluoridate). J. clin. Invest. 37, 350–368 (1958).

    Article  CAS  PubMed  Google Scholar 

  166. Gunther, F. A., G. E. Carman, L. R. Jeppson, J H Barkley and R. C. Blinn: Residual behavior of S-(p-chlorophenylthio)methyl 0,0-diethyl phosphorodithioate (Trithion) on and in mature lemons and oranges. J. Agric. Food Chem. 7, 28–30 (1959).

    Article  CAS  Google Scholar 

  167. Gysin, H.: Sur un nouveau groupe de substances insecticides. III. Int. Congr. Phytopharmacy, Paris, 1952, p. 40.

    Google Scholar 

  168. Gysin, H.: Some new insecticides. Chimia 8, 205–210, 221–228 (1954).

    Google Scholar 

  169. Gysin, H., u. A. Margot: DBP. 910,652 v. 20. 4. 1952.

    Google Scholar 

  170. Gysin, H., u. A. Margot: Chemistry and toxicological properties of O,O-diethyl-0-(2-iso-propyl-4-methyl6-pyrimidinyl) phosphorothioate (Diazinon). J. Agric. Food Chem. 6, 900–903 (1958).

    CAS  Google Scholar 

  171. Hall, S. A., and M. Jacobson: Hexaethyl tetraphosphate and tetraethyl pyrophosphate. Industr. Engng Chem. 40, 694–699 (1948).

    Article  CAS  Google Scholar 

  172. Hanzal, R. F., H. J. Horn and L. W. Hazleton: Anticholinesterase activity of parathion and malathion. Fed. Proc. 13, 363–364 (1954).

    Google Scholar 

  173. Hardy, E. E., and G. M. Kosolapoff: U.S. Pat. 1946. 2, 409, 039.

    Google Scholar 

  174. Hartley, G. S.: Unpublished experiments. Pest Control, Ltd., Cambridge.

    Google Scholar 

  175. Hartley, G. S.: Brit. Pat. 688, 766, 1949.

    Google Scholar 

  176. Hartley, G. S.: Congress abstracts, III. Int. Congr. Phytopharmacy Paris 1952.

    Google Scholar 

  177. Haste, A., and M. Bargar: Prispevok k. farmakodynamike Dipterex (Beitrag zur Pharmakodynamik des Insektizids Dipterex). Biologia (Bratislava) 13, 428–439 (1958).

    Google Scholar 

  178. Hazard, R., J. Cheymol, P. Chabrier et A. Carayon-Gentil: Sur de nouveaux esters phosphorylés de la choline. C. R. Acad. Sci. (Paris) 243, 2180–2186 (1956).

    CAS  Google Scholar 

  179. Hazifton, L. W., and E. G. Holland: Toxicity of Malathion. A.M.A. Arch. industr. Hyg. 8, 399 405 (1953).

    Google Scholar 

  180. Healy, J. K.: Ascending paralysis following malathion intoxication: a case report. Med. J. Aust. 46, 765 (1959).

    Google Scholar 

  181. Heap, R., and B. C. Saunders: Esters containing phosphorus. Part VII. Substituted diaminofluorophosphine oxides. J. chem. Soc. 1948, 1313–1316.

    Google Scholar 

  182. Heath, D. F.: Reactions of ethylthioethyl 0,0-dimethyl phosphorothioates in water. J. chem. Soc. 1958, 1643–1651.

    Google Scholar 

  183. D. F. Heath, D. W. J. Lane and M. Llewellyn: Commercial octamethylpyrophosphoramide. III. Decomposition of the insecticide in plants using phosphorous as a tracer. J. Sci. Food Agric. 3, 60–69 (1952).

    Article  CAS  Google Scholar 

  184. D. F. Heath, D. W. J. Lane and M. Llewellyn:Commercial octamethylphosphoroamide. IV. Decomposition of pyrophosphorie acid tetra (dimethylamide) and orthophosphoric acid tri(dimethylamide) in the living plant. J. Sci. Food Agric. 3, 69–73 (1952).

    Article  CAS  Google Scholar 

  185. D. F. Heath, and M. Vandeear: Some spontaneous reactions of 0,0-dimethyl S-ethylthioethyl phosphorothiolate and related compounds in water and on storage, and their effects on the toxicological properties of the compounds. Biochem. J. 67, 187–201 (1957).

    CAS  PubMed  Google Scholar 

  186. Hecht, G., u. W. Wirth: Zur Pharmakologie der Phosphorsäureester. Naunyn-Schmiedeberg’s Arch. exp. Path. Pharmak. 211, 264–277 (1950).

    CAS  Google Scholar 

  187. Henglein, A., u. G. Schrader: Zur Kenntnis der Isomerie-Erscheinungen bei den System-Insektiziden „Systox“ und „Metasystox”. Z. Naturforsch. 10 b, Heft 1 (1955).

    Google Scholar 

  188. Henglein, A., u. G. Schrader u. R. Mühlmann: Quantitative infrarotspektroskopische Bestimmung des Isomerenverhältnisses in dem System-Insecticid „Systox“. Z. analyt. Chemie 141, 276–281 (1954).

    CAS  Google Scholar 

  189. Henschler, D., u. H.-H. Bayer: Toxikologische Untersuchungen über Triphenylphosphat, Trixylphosphate und Triarylphosphate aus Mischungen homologer Phenole. Naunyn-Schmiedeberg’s Arch. exp. Path. Pharmak. 233, 512–517 (1958).

    CAS  Google Scholar 

  190. Hewitt, R., A. Brebbia and E. Waletsky: Carbamoyl alkyl phosphorodithioates as chemotherapeutic agents. J. econ. Ent. 51, 126–131 (1958).

    CAS  Google Scholar 

  191. Heymans, C., A. Pochet et H. VAN Houtte: Contributions it la pharmacologie du Sarin et du Tabun. Arch. int. Pharmacodyn. 104, 293–332 (1956).

    CAS  Google Scholar 

  192. Hilgetag, G., u. G. Lehmann: Optisch aktive Thiophosphate. J. prakt. Chem. 8, 224 bis 234 (1959).

    Google Scholar 

  193. Hobbiger, F.: The inhibition of cholinesterases by 3-(diethoxyphosphinyloxy)-N-methylquinolinium methylsulphate and its tertiary base. Brit. J. Pharmacol. 9, 159–165 (1954a).

    CAS  PubMed  Google Scholar 

  194. Hobbiger, F. Anticholinesterases. A comparison between the in vitro activity and the in vivo action of certain organic phosphates. Chem. and Ind. 1954b, p. 1574.

    Google Scholar 

  195. Hodge, H. C., E. A. Maynard, L. Hurwitz, V. Distefano, W. L. Downs, C. K. Jones and H. J. Blanchet JR.: Studies of the toxicity and of the enzyme kinetics of ethyl p-nitrophenyl thionobenzene phosphonate (EPN). J. Pharmacol. 112, 29–39 (1954).

    CAS  Google Scholar 

  196. Hoegberg, E. I., and J. T. Cassaday: The reaction of 0,0-dialkyl thiophosphoric acid salts with some a-haloacyl derivatives. J. Amer. chem. Soc. 73, 557–559 (1951).

    Article  CAS  Google Scholar 

  197. Hofmann, A. W.: Weitere Beobachtungen über die Phosphinsäuren. Ber. 6, 303–308 (1873).

    Google Scholar 

  198. Holmstedt, B.: Synthesis and pharmacology of dimethylamidoethoxy-phosphoryl cyanide (Tabun) together with a description of some allied anticholinesterase compounds containing the N—P bond. Acta physiol. scand. 25, 1–120, Suppl. 90 (1951).

    Google Scholar 

  199. Holmstedt, B.: A modification of the thiocholine method for the determination of cholinesterase. I. B.ochemical evaluation of selective inhibitors. Acta physiol. scand. 40, 322–330 (1957).

    Google Scholar 

  200. Holmstedt, B.: Pharmacology of organophosphorus cholinesterase inhibitors. Pharm. Rev. 11, 567–688 (1959).

    Google Scholar 

  201. Holmstedt, B.and C. R. SE Oglund: The action on spinal reflexes of dimethyl-amido-ethoxyphosphoryl cyanide. “Tabun,” a cholinesterase inhibitor. Acta physiol. scand. 29, 410–427 (1953).

    Google Scholar 

  202. Holtz, P., u. E. Westerman: Giftung und Entgiftung von Parathion und Paraoxon. Naunyn-Schmiedeberg’s Arch. exp. Path. Pharmak. 237, 211–221 (1959).

    CAS  Google Scholar 

  203. Hopf, H. S., and R. T. Taylor: Role of cholinesterase in insecticidal action. Nature (Lond.) 182, 1381–1382 (1958).

    Article  CAS  Google Scholar 

  204. Horton, R. G., G. B. Koelle, B. P. Mcnamara and H. J. Pratt: The acute toxicity of di-isopropyl fluorophosphate. J. Pharmacol. 87, 414–420 (1946).

    CAS  Google Scholar 

  205. Hoskin, F. C. G.: The enzymatic hydrolysis products of sarin. Canad. J. Biochem. 34, 75–79 (1956).

    CAS  PubMed  Google Scholar 

  206. Hoskin, F. C. G., and G. S. Trick: Stereospecificity in the enzymatic hydrolysis of tabun and acetylß-methylcholine chloride. Canad. J. Biochem. 33, 963–969 (1955).

    Article  CAS  PubMed  Google Scholar 

  207. Illyucitenok, T. Yu.: Effect of organophosphorus compounds on salivation and intestinal secretion. Khim. i Primenenie Fosfororg. Soedinenii, Akad. Nauk S.S.S.R., Trudy 1-oi Konferents, 1955, pp. 318–323.

    Google Scholar 

  208. Iwamoto, T., and M. Taga: Effects of methylparathion on the cow and its distribution in the body. Igaku to Seibutsugaku 50, 54–57 (1956).

    CAS  Google Scholar 

  209. Jandorf, B. J.: Mode of action of pesticides. Mechanism of reaction of di-n-propyl2,2-dichlorovinyl phosphate (DDP) with esterases. J. Agric. Food Chem. 4, 853–858 (1956).

    Article  CAS  Google Scholar 

  210. Jandorf, B. J., and P. D. Mcnamara: Distribution of radiophosphorus in rabbit tissues after injection of phosphorus-labeled diisopropyl fluorophosphate. J. Pharmacol. 98, 77–84 (1950).

    CAS  Google Scholar 

  211. B. J. Jandorf, H. O. Michel, N. K. Schaffer, R. Egan and W. H. Summerson: General discussion on the physical chemistry of enzymes. Faraday Soc. (Oxford, 10–12 August) 12, 4808 (1955).

    Google Scholar 

  212. The mechanism of reaction between esterases and phosphorus-con- taining anti-esterases. Disc. Faraday Soc. 20, 134–142 (1955).

    Article  Google Scholar 

  213. B. J. Jandorf T. Wagner-Jauregg, J. J. Oneill and M. A. Stolberg: The reaction of phosphorus-containing enzyme inactivators with phenols and polyphenols. J. Amer. chem. Soc. 74, 1521–1523 (1952).

    Article  Google Scholar 

  214. Jean, H.: Esters et sels de la choline et de quelques acides dérivés du phosphore. Bull. Soc. chim. Fr. 1957, 783–786.

    Google Scholar 

  215. Jewell, H. A., and R. A. Lehman: Pharmacology of phospholine iodide-an alkyl phosphothiocholine. Fed. Proc. 17, 381 (1958).

    Google Scholar 

  216. Johnson, G. A., J. H. Pletcher, K. G. Nolan and J. T. Cassaday: Decreased toxicity and cholinesterase inhibition in a new series of dithiophosphates. J. econ. Ent. 45, 279–283 (1952).

    CAS  Google Scholar 

  217. Jones, H. W., B. J. Meyer and L. Karel: The relationship of cholinesterase inhibiting activity to the toxicity of some organic phosphorus compounds. J. Pharmacol. 94, 215 to 220 (1948).

    Google Scholar 

  218. Jung, O.: Toxikologie des Dithiophosphorsäureesters Azethion. Arch. Tox. 16, 341–345 (1957).

    Article  CAS  Google Scholar 

  219. Kabacnik, M. E., N. A. Godovikov, D. M. Pajkin, A. M. P. Saranov, L. F. Efimova and N. M. Gamrer: Organophosphorus insecticides (in Russian) rlurnal obscej chimii, T. 29, 7, 2182–2190 (1959).

    Google Scholar 

  220. Kaplanis, J. N., D. E. Hopkixs and G. H. Treiber: Dermal and oral treatments of cattle with phosphorus-32-labeled Co-Ral. J. Agric. Food Chem. 7, 483–486 (1959).

    Article  CAS  Google Scholar 

  221. Kay, K., L. Monkman, J. P. Windish, T. Doherty, J. Paré and C. Racicot: Parathion exposure and cholinesterase response of Quebec apple growers. A.M.A. Arch. industr. Hyg. 6, 252–262 (1952).

    CAS  Google Scholar 

  222. Ketelaar, J. A. A.: Abstr. II. Int. Congr. Crop Protection, 1949.

    Google Scholar 

  223. Ketelaar, J. A. A., and J. E. Hellingman: Chemical studies on insecticides. Analyt. Chem. 23, 646–650 (1951).

    Article  CAS  Google Scholar 

  224. Ktby, B. A.: Alkyl Fluorophosphonates and Related Compounds. Research 2, 417–422 (1949).

    Google Scholar 

  225. Ktby, B. A., and M. Kelby: The toxicity of alkyl fluorophosphonates in man and animals. Brit. J. Pharmacol. 2, 234–240 (1947).

    Google Scholar 

  226. Kilpatrick, M. L., and M. Kilpatrick: The hydrolysis of diisopropyl fluophosphate. J. phys. Chem. 53, 1371–1384 (1949).

    Article  CAS  Google Scholar 

  227. Kilpatrick, M. L., and M. Kilpatrick: A mechanism for the hydrolysis of diisopropyl fluophosphate. J. phys. Chem. 53, 1385–1397 (1949).

    Article  CAS  Google Scholar 

  228. Klimmer, O. R., u. W. Pfaff: Untersuchungen über die Toxicität des neuen Kontaktinsekticides 0,0-Dimethyl-thiophosphorsäure-O-(ß-S-äthyl)-äthylester („Metasystox“). Arzneim.-Forsch. 5, 584–587 (1955).

    CAS  Google Scholar 

  229. Klimmer, O. R., u. W. Pfaff: Vergleichende Untersuchungen über die Toxicität organischer Thiophosphorsäureester. Arzneim.-Forsch. 5, 626–630 (1955).

    CAS  Google Scholar 

  230. Klotzsche, C.: Zur Toxikologie neuerer insektizider Phosphorsäureester. Arzneim.Forsch. 5, 436–439 (1955).

    CAS  Google Scholar 

  231. Klotzsche, C.: Neue Insektizide Phosphor-und Phosphorsäureester. Nachrbl. deutsch. Pflanzenschutzdienst 10, 60 (1958).

    Google Scholar 

  232. Kodama, J. K., H. H. Anderson, M. K. Dunlap and C. H. Hine: Toxicity of organo-phosphorus compounds. A M.A Arch. industr. Hlth 11, 487–493 (1955).

    CAS  Google Scholar 

  233. Kodama, J. K., M. S. Morse, H. H. Anderson, M. K. dunlap and C. H. Hine: Comparative toxicity of two vinyl-substituted phosphates. A.M.A. Arch. industr. Hyg. 9, 45–61 (1954).

    CAS  Google Scholar 

  234. Koelle, G. B., and A. Gilman: The relationship between cholinesterase inhibition and the pharmacological action of di-isopropyl fluorophosphate (DFP). J. Pharmacol. 87, 421–434 (1946).

    CAS  Google Scholar 

  235. Koelle, G. B., and A. Gilman The chronic toxicity of diisopropyl fluorophosphate (DFP) in dogs, monkeys and rats. J. Pharmacol. 87, 435–448 (1946).

    CAS  Google Scholar 

  236. Koelle, G. B., and E. C. Steiner: The cerebral distributions of a tertiary and a quaternary anti-cholinesterase agent following intravenous and intraventricular injection. J. Pharmacol. 118, 420–434 (1956).

    CAS  Google Scholar 

  237. Koll, W.: Personal communication. In letter to the author, March 3, 1960.

    Google Scholar 

  238. Kosolapoff, G. M.: Organophosphorus compounds. New York: John Wiley and Sons, Inc.; New York: Chapman & Hall, Ltd., 1950.

    Google Scholar 

  239. Kovache, H., H. Jean and G. Garnier: Étude de quelques composés organiques du phosphore. Chim et Industr. 64, 287–299 (1950).

    CAS  Google Scholar 

  240. Kaoi, S., and A. M. Kunkel: Observations on the pharmacology of the anticholinesterases sarin and tabun. Proc. Soc. exp. Biol. (N. Y.) 86, 530–533 (1954).

    Article  Google Scholar 

  241. Krueger, H. R., J. E. Casida and R. P. Niedermeier: Bovine metabolism of organo-phosphorus insecticides. Metabolism and residues associated with dermal application of Co-ral to rats, a goat, and a cow. J. Agric. Food Chem. 7, 182–188 (1959).

    Article  CAS  Google Scholar 

  242. Lange, W.: Fortschritte auf dem Gebiete der Darstellung und Verwendung von Fluorverbindungen. Chem. Ztg. 59, 393 (1935).

    CAS  Google Scholar 

  243. Lange, W.: Personal letter to the author. April 7, 1952.

    Google Scholar 

  244. Lange, W.:, u. G. vox Krueger: Über Ester der Monofluorphosphorsäure. Ber. dtsch. chem. Ges. 65, 1598–1601 (1932).

    Article  Google Scholar 

  245. Larsson, L.: The hydrolysis of dimethylamido-ethoxyphosphoryl cyanide (Tabun). Acta chem. scand. 7, 306–314 (1953).

    Article  CAS  Google Scholar 

  246. Larsson, L.: The alkaline hydrolysis of isopropoxy-methyl-phosphoryl fluoride (Sarin) and some analogues. Acta chem. scand. 11, 1131–1142 (1957).

    Article  CAS  Google Scholar 

  247. Larsson, L.: Studies on the chemical reactivity of organic phosphorus compounds. Diss. Svensk kem. Tidskr. 70, 405 427 (1958).

    Google Scholar 

  248. Larsson, L. B. Holmstedt and E. Tjus: Some considerations regarding the nomenclature of organic phosphorus compounds. Acta chem. scand. 8, 1563–1569 (1954).

    Article  CAS  Google Scholar 

  249. Lendle, L.: Personal communication (1959).

    Google Scholar 

  250. Lindquist, D. A., E. C. Burns, C. P. Pant and P. A. Dahm: Fate of P32-labeled Bayer 21/199 in the white rat. J. econ. Ent. 51, 204–206 (1958).

    CAS  Google Scholar 

  251. Locker, A., u. H. Siedek: Über Aktivierung von Cholinesterasen durch Alkylphosphate in vivo. Experientia (Basel) 8, 146–148, 302–303 (1952).

    Google Scholar 

  252. Locker, A., u. H. Siedek: Die Wirkung von Alkylphosphaten auf Gewebsatmung und Cholinesteraseaktivität. Z. ges. exp. Med. 119, 314–326 (1952).

    Article  CAS  PubMed  Google Scholar 

  253. Lorenz, W.:Farbenfabriken Bayer. DBP. 927, 270.

    Google Scholar 

  254. Lorenz, W.: Insecticidal phosphonic ester. U.S. Pat. 2, 701, 225.

    Google Scholar 

  255. W.Lorenz, A. Henglein and G. Schrader: The new insecticide, 0,0-dimethyl 2,2,2-trichloro1-hydroxy-ethylphosphonate. J. Amer. chem. Soc. 77, 2554–2556 (1955).

    Google Scholar 

  256. Louloudes, S. J., J. N. Kaplanis and C. C. Roan: The synthesis of radioactive Diazinon using 1332. J. org. Chem. 21, 685–686 (1956).

    Article  CAS  Google Scholar 

  257. Mackworth, J. F., and E. C. Webb: The inhibition of serum cholinesterase by alkyl fluorophosphonates. Biochem. J. 42, 91–95 (1948).

    CAS  PubMed  Google Scholar 

  258. March, R. B., T. R. Fukuto, R. L. Metcalf and M. G. Maxon: Fate of P32-labeled malathion in the laying hen, white mouse, and American cockroach. J. econ. Ent. 49, 185–195 (1956).

    CAS  Google Scholar 

  259. R. B.March, R. L. Metcalf, T. R. Funuto and F. A. Gunther: Fate of P32-labeled malathion sprayed on Jersey heifer calves. J. econ. Ent. 49, 679–682 (1956).

    Google Scholar 

  260. Marsi, K. L., C. A. Vanderwerf and W. E. Mcewen: The synthesis and resolution of compounds of tetracovalent phosphorus. J. Amer. chem. Soc. 78, 3063–3066 (1956).

    Article  CAS  Google Scholar 

  261. Martin, H.: Guide to chemicals used in crop protection. Canad. Dept. agric. Bull., 3rd Ed., October 1957, p. 136.

    Google Scholar 

  262. Marrsox, A. M., J. T. Spillaner and G. W. Pearce: Dimethyl 2,2-dichlorovinyl phosphate (DDVP), an organic phosphorus compound highly toxic insects. J. Agric. Food Chem. 3, 319–321 (1955).

    Article  Google Scholar 

  263. Mccollister, D. D., F. Open and V. K. Rowe: Toxicological studies of 0,0-dimethylO-(2,4,5-trichlorophenyl) phosphorothioate (Ronne’) in laboratory animals. J. Agric. Food Chem. 7, 689–693 (1959). Handb. d. exp. Pharmakol. Erg. W. Bd. XV 31

    Google Scholar 

  264. Mccommns, H., B. C. Saunders and G. J. Stacey: Esters containing phosphorus. Part III. J. chem. Soc. 1945, 921–922.

    Google Scholar 

  265. Mcisaac, R. J., and G. B. Koelle: Comparison of the effects of inhibition of external, internal and total acetylcholinesterase upon ganglionic transmission. J. Pharmacol. 126, 9–20 (1959).

    CAS  Google Scholar 

  266. Mclvoa, R. A., G. D. Mccarthy and G. A. Grant: Preparation and toxicity of some alkyl thiopyrophosphates. Canad. J. Chem. 34, 1819–1832 (1956).

    Article  Google Scholar 

  267. Meeter, E.: The relation between end-plate depolarization and the repetitive response elicited in the isolated rat phrenic nerve-diaphragm preparation by DFP. J. Physiol. 144, 38–51 (1958).

    CAS  PubMed  Google Scholar 

  268. Metcalf, R. L.: Organic insecticides. Their chemistry and mode of action. New York and London: Interscience Publishers 1955.

    Google Scholar 

  269. Metcalf, R. L. ed.: Advances in pest control research. Vol. 1. New York and London: Interscience Publishers 1957.

    Google Scholar 

  270. R. L.Metcalf, T. R. Fuguto and R. B. March:Plant metabolism of dithio-Systox and Thimet. J. econ. Ent. 50, 338–345 (1957).

    Google Scholar 

  271. R. L.Metcalf: Toxic action of Dipterex and DDVP to the house fly. J. econ. Ent. 52, 44 49 (1959).

    Google Scholar 

  272. R. L.Metcalf,and R. B. March: Studies of the mode of action of parathion and its derivatives and their toxicity to insects. J. econ. Ent. 42, 721–728 (1949).

    CAS  Google Scholar 

  273. R. L.Metcalf,and R. B. March: Properties of acetylcholine esterases from the bee, the fly and the mouse and their relation to insecticide action. J. econ. Ent. 43, 670–677 (1950).

    CAS  Google Scholar 

  274. R. L.Metcalf,and R. B. March: The isomerization of organic thionophosphate insecticides. J. econ. Ent. 46, 288–294 (1953).

    CAS  Google Scholar 

  275. R. L.Metcalf,and R. B. March T. R. Fukuto and M. G. Maxon: The nature and significance of Systox residues in plant materials. J. econ. Ent. 48, 364 369 (1955).

    Google Scholar 

  276. R. L.Metcalf E. M. Stafford, T. R. Fukuto and R. B. March: The systemic behavior of 0,0-diethyl S-2-(diethylamino) ethyl phosphorothiolate and its salts. J. econ. Ent. 50, 205 to 210 (1957).

    CAS  Google Scholar 

  277. Meyer, F.: Untersuchungen über 17 neue Dialkyl-dihalogenvinyl-und tetrahalogenäthyl-phosphate. IV. Mitteilung: Kreislauf-und Atemwirkung der übrigen Dialkyldichlorvinyl-und tetrachloräthylphosphate. Arzneimittel-Forsch. 5, 646–654 (1955); and previous papers in the same series.

    Google Scholar 

  278. Michaelis, C. A. A.: Über die organischen Verbindungen des Phosphors mit Stickstoff. Liebigs Ann. Chem. 326, 129–258 (1903).

    Article  CAS  Google Scholar 

  279. Modell, W., S. Krop, T. Hrrcncocx and W. F. Riker jr.: General systemic actions of di-isopropyl fluorophosphate (DFP) in cats. J. Pharmacol. 87, 400–413 (1946).

    CAS  Google Scholar 

  280. Morse, M. S., J. K. Kodama and C. H. Hrne: Cholinesterase-inhibiting properties of two vinyl-substituted phosphates. Proc. Soc. exp. Biol. (N. Y.) 83, 765–768 (1953).

    Article  CAS  Google Scholar 

  281. Moyle, C. L.(to The Dow Chemical Co.): U.S. Patent 2,599–516 (June 3, 1952 ).

    Google Scholar 

  282. Murrhy, S. D., R. L. Anderson and K. P. Dubois: Potentiation of toxicity of Malathion by triorthotolyl phosphate. (24668). Proc. Soc. exp. Biol. (N. Y.) 3, 483–487 (1959).

    Article  Google Scholar 

  283. Murrhy, S. D., and K. P. Dubois: Enzymatic conversion of the dimethoxy ester of benzotriazine dithiophosphoric acid to an anticholinesterase agent. J. Pharmacol. 119, 572–583 (1957).

    Google Scholar 

  284. Murrhy, S. D., and K. P. Dubois: Quantitative measurement of inhibition of the enzymic detoxification of malathion by EPN (ethyl p-nitrophenyl thionobenzenephosphonate). Proc. Soc. exp. Biol. (N. Y.) 96, 813–818 (1957).

    Article  Google Scholar 

  285. Murrhy, S. D., and K. P. Dubois: Inhibitory effect of dipterex and other organic phosphates on detoxification of malathion. Fed. Proc. 17, 397 (1958).

    Google Scholar 

  286. Murrhy, S. D., and K. P. Dubois: The influence of various factors on the enzymatic conversion of organic thiophosphates to anticholinesterase agents. J. Pharmacol. 124, 194–202 (1958).

    Google Scholar 

  287. Mühlmann, R., u. H. Tietz: Das chemische Verhalten von Methylisosystox in der lebenden Pflanze und das sich daraus ergebende Rückstandsproblem. Höfchen-Briefe, Bayer (Leverkusen, Germany) Pflanzenschutz-Nachr. 9, 116–140 (1956).

    Google Scholar 

  288. Myers, D. K.: Studies on selective esterase inhibitors. Thesis, pp. 97. Amsterdam 1954.

    Google Scholar 

  289. Myers, D. K.: Neue chemische Kampfstof fe. Protar 16, 131–135 (1950).

    Google Scholar 

  290. Nylén, P.: Studien über organische Phosphorverbindungen. Diss., Uppsala 1930.

    Google Scholar 

  291. Obrien, R. D.: The inhibition of cholinesterase and succinoxidase by malathion and its isomer. J. econ. Ent. 49, 484–490 (1956).

    CAS  Google Scholar 

  292. Obrien, R. D.: Properties and metabolism in the cockroach and mouse of malathion and malaoxon. J. econ. Ent. 50, 159–164 (1957).

    CAS  Google Scholar 

  293. Obrien, R. D.: The effect of malathion and its isomer on carbohydrate metabolism of the mouse, cockroach and house fly. J. econ. Ent. 50, 79–84 (1957).

    CAS  Google Scholar 

  294. Obrien, R. D.: Effect of ionization upon penetration of organophosphates to the nerve cord of the cockroach. J. econ. Ent. 52, 812–816 (1959).

    CAS  Google Scholar 

  295. Obrien, R. D., G. D. Thorn and R. W. Fisher: New organophosphate insecticides developed on rational principles. J. econ. Ent. 51, 714–718 (1958).

    CAS  Google Scholar 

  296. Obrien, R. D., and L. S. Wolfe: The metabolism of Co-ral (Bayer 21/199) by tissues of the house fly, cattle grub, ox, rat, and mouse. J. econ. Ent. 52, 692–695 (1959).

    CAS  Google Scholar 

  297. Okinaka, A. J., J. Doull, J. M. Coon and K. P. Dubois: Studies on the toxicity and pharmacological actions of bis(dimethylamido) fluorophosphate (BFP). J. Pharmacol. 112, 231–245 (1954).

    CAS  Google Scholar 

  298. Oosterbaan, R. A., M. G. P. J. Warringa, H. S. Jansz, F. Berends and J. A. Cohen: The reaction of pseudocholinesterase with diisopropyl-phosphorofluoridate (DFP). IV. Int. Congr. Biochem., Wien, 1.-6. Sept. 1958. Suppl. to Int. Abstr. Biol. Sci., p. 38.

    Google Scholar 

  299. Pankaskie, J. E., F. C. Fountaine and P. A. Daum: The degradation and detoxication of parathion in dairy cows. J. econ. Ent. 45, 51–60 (1952).

    CAS  Google Scholar 

  300. Parker, G. F. jr., and W. R. Chattin: A case of malathion intoxication in a ten year old girl. J. Ind. med. Ass. 48, 491–492 (1955).

    Google Scholar 

  301. Paulet, G.: Nouvelle contribution à l’étude de l’action pharmacologique du tétraéthylpyrophosphate (TEPP). Arch. hit. Pharmacodyn. 97, 157–185 (1954).

    CAS  Google Scholar 

  302. Paulet, G.: Activité cholinestérasique et fonctionnement des centres respiratoires. J. Physiol. (Paris) 48, 915–936 (1956).

    CAS  Google Scholar 

  303. Perkow, W.: Die Insektizide. 1. Aufl. Heidelberg: Alfred Hüthig 1956.

    Google Scholar 

  304. Petty, C. H.: Organic phosphate insecticide poisoning. Residual effects in two cases. Amer. J. Med. 24, 467 (1958).

    Article  CAS  PubMed  Google Scholar 

  305. Pianka, M.: Organophosphorus compounds. I. Interaction of organic phosphorohalogenides with solid alkalis A new synthesis of Schradan. J. appl. Chem. 5, 109–120 (1955).

    CAS  Google Scholar 

  306. Pianka, M., and B. D. Owen: Organophosphorus compounds. II. Interaction of dimethylphoshoramidic dichloride with hexamethyl-phosphoramide: Adduct formation and radical exchange. J. apppl. Chem. 5, 525–535 (1955).

    Article  CAS  Google Scholar 

  307. Plarp, F. W., and J. E. Casida: Animal metabolism of insecticides. Bovine metabolism of organophosphorus insecticides. Metabolic fate of 0,0-dimethyl O-(2,4,5-trichlorophenyl) phosphorothioate in rats and a cow. J. Agric. Food Chem. 6, 662–667 (1958).

    Article  Google Scholar 

  308. Plarp, F. W., and J. E. Casida: Hydrolysis of the alkylphosphate bond in certain dialkyl aryl phosphorothioate insecticides by rats, cockroaches, and alkali. J. econ. Ent. 51, 800–803 (1958).

    Google Scholar 

  309. Punte, C. L., E. J. Owens, E. H. Krackow and P. L. Cooper: Influence of physical activity on the toxicity of aerosols and vapors. A. M. A. Arch. industr. Hlth 17, 34–37 (1958).

    CAS  Google Scholar 

  310. Radeleff, R. D., and G. T. Woodward: Toxicological studies of Dow ET-57 in cattle and sheep. J. econ. Ent. 50, 249–251 (1957).

    CAS  Google Scholar 

  311. Razumov, A. I., O. A. Mukhacheva and E A Markovich: Biologically active alkylated amide esters and mixed esters of alkylphosphonic acids. Khim. i. Primenic Fosfororg. Soedinenii, Akad. Nauk S.S.S.R., Trudy 1-oi Konferents, 1955, 194–204 (publ. 1957 ).

    Google Scholar 

  312. Reut, N. A.: Pharmacological and toxicological properties of thiophosphorus compounds. Khim. i. Primenenie Fosfororg. Soedinenii, Akad. Nauk S.S.S.R., Trudy 1-oi Konferents, 1955 pp. 313–317.

    Google Scholar 

  313. Reynolds, H. T., T. R. Fukuto, R. L. Metcalf and R. B. March: Seed treatment of field crops with systemic insecticides. J. econ. Ent. 50, 527–539 (1957).

    CAS  Google Scholar 

  314. Robbins, W. E., T. L. Hopkins and G. W. Eddy: The metabolism of Pia-labeled Bayer L 13/59 in a cow. J. econ. Ent. 49, 801–807 (1956).

    CAS  Google Scholar 

  315. Robbins, W. E., T. L. Hopkins and G. W. Eddy:Metabolism and excretion of phosphorus-32-labeled diazinon in a cow. J. Agric. Food Chem. 5, 509–513 (1957).

    Article  CAS  Google Scholar 

  316. Rosenberg, P., and J. M. Coon: Potentiation between cholinesterase inhibitors. Fed. Proc. 17, 406 (1958).

    Google Scholar 

  317. Sakai, F., H. Dalri, W. D. Erdmann u. G. Schmidt: Über die Atemlähmung durch Parathion oder Paraoxon und ihre antagonistische Beeinflußbarkeit. Naunyn-Schmiedeberg’s Arch. exp. Path. Pharmak. 234, 210–219 (1958).

    CAS  Google Scholar 

  318. Sanderson, D. M., and E. F. Edson: Oxime therapy in poisoning by six organophosphorus insecticides in the rat. J. Pharm. (Lond.) 11, 721–729 (1959).

    Article  CAS  Google Scholar 

  319. Santi, R., and P. DE Pietri-Touelli: Mode of action and biological properties of the S-(methylcarbamyl)methyl 0,0-dimethyl-dithiophosphate. Nature (Lond.) 183, 398 (1959).

    Article  CAS  Google Scholar 

  320. Saunders, B. C.: Phosphorus and fluorine. The chemistry and toxic action of their organic compounds. Cambridge: University Press 1957.

    Google Scholar 

  321. Saunders, B. C., and G. J. Stacey: Esters containing phosphorus. Part IV. Diisopropyl fluorophosphonate. J. them. Soc. 1948, 695–699.

    Google Scholar 

  322. Saunders, B. C., and G. J. Stacey F. Wild and J. G. E. Wilding: Esters containing phosphorus. Part V. Esters of substituted phosphonic and phosphonous acids. J. them. Soc. 1948, 699–703.

    Google Scholar 

  323. Scaife, J. E., and D. H. Campbell: The destruction of O,0-diethyl-S-2-diethylaminoethyl phosphorothiolate by liver microsomes. Canad. J. Biochem. 37, 297–305 (1959).

    Article  CAS  PubMed  Google Scholar 

  324. Schall, A.: Über die Einwirkung von Phosphoroxybromid auf sek. a liphatische Amine Dissert. Rostock 1898; Liebigs Ann. Chem. 326, 182 (1903).

    Google Scholar 

  325. Schaumann, W., and C. Job: Differential effects of quaternary cholinesterase inhibitor, phospholine, and its tertiary analogue, compound 217-AO, on central control of respiration and on neuromuscular transmission. The antagonism by 217-AO the respiratory arrest caused by morphine. J. Pharmacol. 123, 114–120 (1958).

    CAS  Google Scholar 

  326. Schrader, G.: Belgian Patent 556,009.

    Google Scholar 

  327. Schrader, G.: DBP. 720,577.

    Google Scholar 

  328. Schrader, G.: DBP. 918,603.

    Google Scholar 

  329. Schrader, G.: DBP. 814,297 v. 2. 10. 1948.

    Google Scholar 

  330. Schrader, G.: DBP. 881,194 v. 31. 7. 1951.

    Google Scholar 

  331. Schrader, G.: DBP. 921,870 v. 3. 5. 1952.

    Google Scholar 

  332. Schrader, G.: DAS. 10,101,960 v. 13. 10. 1955.

    Google Scholar 

  333. Schrader, G. and H. Kükenthal: DBP. 918,603 v. 5. 8. 1941.

    Google Scholar 

  334. Schrader, G. and W. Lorenz: DBP. 876,692 v. 7.7. 1951; DBP. 876,691 v. 6. 7. 1951; DBP. 871,448 v. 31. 7. 1951.

    Google Scholar 

  335. Schrader, G. and W. Lorenz: DBP. 917,668 v. 2. 8. 1952.

    Google Scholar 

  336. Schrader, G: BIOS Final Report, 1947, p. 714.

    Google Scholar 

  337. Schrader, G.: Organische Phosphor-Verbindungen als neuartige Insektizide (Auszug). Angew. Chem. 62, 471–473 (1950).

    Article  CAS  Google Scholar 

  338. Schrader, G.: Die Entwicklung neuer Insektizide auf Grundlage von organischen Fluor-und Phosphorverbindungen. Monographie No. 62, 2. Aufl. Weinheim: Verlag Chemie 1952.

    Google Scholar 

  339. Schrader, G. Chiorothion, a new relatively nontoxic insecticide from the series of the thiophosphoric acid esters. Angew. Chem. 66, 265–267 (1954).

    Article  CAS  Google Scholar 

  340. Schrader, G. Die insektiziden Phosphorsäureester. Angew. Chem. 69, 86–90 (1957).

    Google Scholar 

  341. Scott, M. J.: The effects of anticholinesterases upon the spleen of the dog. J. Physiol. 139, 489–496 (1957).

    CAS  PubMed  Google Scholar 

  342. Shugaev, B. B.: Alkyl pyrophosphates, their pharmacological and toxicological properties. Khim. I Primenenie Fosfororg. Soedinenii, Akad. Nauk S.S.S.R., Trudy 1-oi Konferents, 1955, pp. 301–309.

    Google Scholar 

  343. South African Patent 1748/55.

    Google Scholar 

  344. Spencer, E. Y., R. D. Obrien and R. W. White: Permanganate oxidation products of Schradan. J. Agric. Food Chem. 5, 123–127 (1957).

    Article  CAS  Google Scholar 

  345. Stewart, W. C.: The effects of sarin and atropine on the respiratory center and neuromuscular junctions of the rat. Canad. J. Biochem. 37, 651–660 (1959).

    Article  CAS  PubMed  Google Scholar 

  346. Tahmeun, L.-E.: Dialkoxy-phosphorylthiocholines, alkoxy-methyl-phosphorylthiocholines and analogous choline esters. Acta chem. scand. 11, 1340–1349 (1957).

    Article  Google Scholar 

  347. Tahmeun, L.-E.: Methyl-fluoro-phosphorylcholines. Acta chem. scand. 11, 859–865 (1957).

    Article  Google Scholar 

  348. Tahmeun, L.-E.: Choline esters; substrates and inhibitors of cholinesterases. Svensk kern. Tidskr. 70, 157–181 (1958).

    Google Scholar 

  349. Tahmeun, L.-E.: Organophosphorylcholines and cholinesterases. Ark. kemi 12, 287–298 (1958).

    Google Scholar 

  350. Tibbling, G.: Unpublished.

    Google Scholar 

  351. Tolkmrrh, H.: Electron group polarizability and molecular properties of organophosphorus compounds. Ann. N. Y. Acad. Sci. 79, 187–231 (1959).

    Google Scholar 

  352. Topley, B.: Insecticidal phosphorus compounds. . 1950, Dec. 30, 859–868.

    Google Scholar 

  353. Toy, A. D. F.: The preparation of tetraethyl pyrophosphate and other tetraalkyl pyrophosphates. J. Amer. chem. Soc. 70, 3882–3886 (1948).

    Article  CAS  Google Scholar 

  354. Toy, A. D. F.: Tetraethyl dithionopyrophosphate and related tetraalkyl dithionopyrophosphates. J. Amer. chem. Soc. 73, 4670–4674 (1951).

    Article  CAS  Google Scholar 

  355. Tsuyuxr, H., M. A. Starmann and J. E. Casida: Preparation, purification, isomerization and biological properties of octamethylpyrophosphoramide N-oxide. J. Agric. Food Chem. 3, 922–932 (1955).

    Article  Google Scholar 

  356. Tuthill, J. W. G.: Malathion poisoning. New Engl. J. Med. 258, 1018–1019 (1958).

    CAS  Google Scholar 

  357. U.S. Pat. 2,503,390.

    Google Scholar 

  358. U.S. Pat. 2,640,847; 2,597,534.

    Google Scholar 

  359. U.S. Pat. 2,685,552.

    Google Scholar 

  360. U.S. Pat. 2,759,010; D.B.P. 947,369.

    Google Scholar 

  361. U.S. Pat. 2,761,806.

    Google Scholar 

  362. U.S. Pat. 2,833,805 and 2,725,328; 2,815,350.

    Google Scholar 

  363. Valade ET Salle: Apercu sur les nouveaux toxiques de guerre. Rev. vêt. Milit. 3, 377–385 (1948).

    Google Scholar 

  364. Valters, M. N. I.: Malathion intoxication. Med. J. Aust. 44, 876–880 (1957).

    Google Scholar 

  365. Vandekar, M.: The toxic properties of demeton-methyl (Metasystox) and some related compounds. Brit. J. Ind. Med. 15, 158–167 (1958).

    CAS  Google Scholar 

  366. Vandekar, M., and D. F. Heath: The reactivation of cholinesterase after inhibition in vivo by some dimethyl phosphate esters. Biochem. J. 67, 202–208 (1957).

    CAS  PubMed  Google Scholar 

  367. van Der Meer, C., and E. Meeter: The mechanism of action of anticholinesterases. II. The effect of diisopropylfluorophosphonate (DFP) on the isolated rat phrenic nerve-diaphragm preparation. Acta physiol. pharm. néerl. 4, 454–471 (1956).

    Google Scholar 

  368. van Wazer, J. R.: Phosphorus and its compounds. Interscience publ. New York 1958.

    Google Scholar 

  369. Webb, E. C.: The biochemical reactions of chemical warfare agents. Biochem. Soc. Symp., No. 2, pp. 50–60. Cambridge 1948.

    Google Scholar 

  370. Wescoe, W. C., and W. F. Biker jr.: The pharmacology of anti-curare agents. Ann N. Y. Acad. Sci. 54, 438–459 (1951).

    Article  CAS  PubMed  Google Scholar 

  371. Wilson, I. B., F. Bergmann and D. Nachmansohn: Acetylcholinesterase. IX. Structural features determining the inhibition by amino acids and related compounds. J. biol. Chem. 186, 693 (1950).

    PubMed  Google Scholar 

  372. Wirth, W.: Zur Pharmakologie der Phosphorsäureester. Diäthyl-p-nitrophenylphosphat. (“Mintacol”). Naunyn-Schmiedeberg’s Arch. exp. Path. Pharmak 207, 547–568 (1949).

    Google Scholar 

  373. Wirth, W.: Zur Pharmakologie der Phosphorsäureester. Diäthylthiophosphorsäureester des Athylthioglykol („Systox-Wirkstoff“). Naunyn-Schmiedeberg’s Arch. exp. Path. Pharmak. 217, 144 152 (1953).

    Google Scholar 

  374. Wirth, W.: Zur Wirkung System-insecticider Phosphorsäure-Ester im Warmblüter-Stoffwechsel. Naunyn-Schmiedeberg’s Arch. exp. Path. Pharmak. 234, 352–363 (1958).

    Google Scholar 

  375. Wollenberg, O.: Kolorimetrische Bestimmung des Insektizides „Gusathion“-„Bayer 17147”. Angew. Chem. 68, 581 (1956).

    Article  CAS  Google Scholar 

  376. Wollenberg, O., u. G. Schrader: Neuer spezifischer Nachweis des Insektizides „Bayer 17147“ („Gusathion”). Angew. Chem. 68, 41 (1956).

    Article  CAS  Google Scholar 

  377. Vrbovsky, L., FR. V. Selecky u. L. Rosrval: Toxikologische und pharmakologische Studien der Phosphorsäureester-Insectiziden. Naunyn-Schmiedeberg’s Arch. exp. Path. Pharmak. 236, 202–205 (1959).

    CAS  Google Scholar 

  378. Wright, P. G.: An analysis of the central and peripheral components of respiratory failure produced by anti-cholinesterase poisoning in the rabbit. J. Physiol. 126, 52–70 (1954).

    CAS  PubMed  Google Scholar 

  379. Yip, G., and J. W. Cook: Malathionase. III. Substrate specificity studies. J. Ass. off. agric. Chem. 42, 405–407 (1959).

    CAS  Google Scholar 

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Holmstedt, B. (1963). Structure-Activity Relationships of the Organophosphorus Anticholinesterase Agents. In: Koelle, G.B. (eds) Cholinesterases and Anticholinesterase Agents. Handbook of Experimental Pharmacology, vol 15. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-99875-1_9

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