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
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).
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).
Adebahr, G.: Nierenveränderungen bei der E 605-Vergiftung des Menschen. Arch. Toxikol. 18, 107–120 (1960).
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).
Adie, P. A.: The purification of sarinase from bovine plasma. Canad. J. Biochem. 34, 1091–1094 (1956).
Adie, P. A.: Studies on the enzymatic hydrolysis of sarin and tabun. Canad. J. Biochem. 36, 15–20 (1958).
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).
Adie, P. A., and J. Tuba: The intracellular localization of liver and kidney sarinase. Canad. J. Biochem. 36, 21–24 (1958).
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).
Aldridge, W. N.: The differentiation of true and pseudo cholinesterase by organ-phosphorus compounds. Biochem. J. 53, 62–67 (1953).
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).
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).
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).
Aldridge, W. N., and A. N. Davison: The mechanism of inhibition of cholinesterases by organophosphorus compounds. Biochem. J. 55, 763–766 (1953).
American Cyanamid Co. U.S. Pat. 2, 664, 437.
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).
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.
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.
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).
Arbusow, A. E.: The Kazan school of chemists. Uspekhi Khim 9, 1378–1394 (1940).
Arbusow, A. E., u. B A Arbusow: Über die Ester der pyrophosphorigen, der Unterphosphor-und der Pyrophosphorsäure. J. prakt. Chem. 238, 103–132 (1931).
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).
Arthur, B. W., and J. E. Casida: Biological and chemical oxidation of tetramethyl phosphordiamidic fluoride (dimefox). J. econ. Ent. 51, 49–56 (1958).
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).
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).
Augustinsson, K.-B.: Mintacol (diethyl p-nitrophenyl phosphate). Svensk farm. Tidskr. 57, 261–267 (1953).
Augustinsson, K.-B.: Biochemical studies with Tabun and allied compounds. Ark. Kemi 6, 331–350 (1953).
Augustinsson, K.-B.: The chemical determination of parathion and its application to biological material. Acta agric. Stand. 7, 165–189 (1957).
Augustinsson, K.-B., and G. Joxssox: Biochemical studies on the degradation products of diazinone. Experientia (Basel) 13, 438–443 (1957).
K.-B.Augustinsson, and D. Nachmansohn: Studies on cholinesterase. VI. Kinetics of the inhibition of acetylcholine esterase. J. biol. Chem. 179, 543–559 (1949).
K.-B.Augustinsson, and D. Nachmansohn: Distinction between acetylcholine-esterase and other choline ester-splitting enzymes. Science 110, 98–99 (1949).
Austin, L., and W. K. Berry: Two selective inhibitors of cholinesterase. Biochem. J. 54, 695–700 (1953).
Bachmann, F: Phosphamidon, ein neuer Phosphorsäureester mit systemischer Wirkung. Summary of Communications, IVth International Congress of Crop Protection 1957, p. 164.
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).
Banister, J., and V. P. Wihttaxer: Pharmacological activity of the carbon analogue of acetylcholine. Nature (Lond.) 167, 605 (1951).
Barnes, J. M., and J. I. Duff: The role of cholinesterase at the myoneural junction. Brit. J. Pharmacol. 8, 334–339 (1953).
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).
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).
W. F. Barthel, P. A. Giang and S. A. Hall: Dialkyl a-hydroxyphosphonates derived from chloral. J. Amer. chem. Soc. 76, 4186–4187 (1954).
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).
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).
Berg; S., E. Kuchinke u. K. Fischer: Zur Kenntnis der Vergiftung mit dem Schädlingsbekämpfungsmittel Potasan G. Arch. Toxikol. 16, 105–117 (1956).
Berry, W. K.: Biochemical mechanism after poisoning with anticholinesterase. Proc. roy. Soc. Med. 46, 801–802 (1953).
Bockel, P.: Vergiftung mit einem Phosphorsäureesterpräparat der Diazinon-Gruppe „Basudin“. Dtsch. med. Wschr. 82, 1230–1231 (1957).
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.
Bodansity, O.: Contributions of medical research in chemical warfare to medicine. Science 102, 517–521 (1945).
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).
Bonnaud: L’arme chimique est-elle périmée? Protar 14, 113–115 (1948).
Bourret, J., L. Derobert u. M. Gueniot: Intoxications volontaires par insecticides organo-phosphorés (Parathion). Aim Méd. lég. 38, 160–164 (1958).
Bowman, J. S.: Further studies on the metabolism of Thimet by plants, insects, and mammals. J. econ. Ent. 51, 838–843 (1958).
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).
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).
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).
Brit. Pat. 688, 760.
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).
Burgen, A. S. V.: The mechanism of action of anticholinesterase drugs. Brit. J. Pharmacol. 4, 219–228 (1949).
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).
Burgen, A. S. V., and F. Hobbiger: The inhibition of cholinesterases by alkylphosphates and alkyl-phenolphosphates. Brit. J. Pharmacol. 6, 593–605 (1951).
Burgen, A. S. V. C. A. Keele and D. Slome: Pharmacological actions of tetraethylpyrophosphate and hexaethyltetraphosphate. J. Pharmacol. 96, 396–409 (1949).
de Candole, C. A.: Successful use of pressor drugs in paraoxon poisoning. Rev. canad. Biol. 15, No. 3 (1956).
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).
W. W. Douglas, and M. K. Mcphan,: Sarin and paraoxon antagonism in different species. Canad. J. Biochem. 35, 1071–1083 (1957).
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).
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).
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).
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).
Cassaday, J. T.: U.S. Pat. 2,578,652 v. 2. 3. 1950.
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.
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).
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).
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).
CIBA/Schweiz, DBP. 845,226.
de Clermont, PH.: Note sur la préparation de quelques éthers. (Séance du lundi 14 août 1854). C. R. 39, 338–340 (1854).
de Clermont, PH.: Mémoire sur les éthers phosphoriques. Ann. Chim. Phys. 44, 330–336 (1855).
Coates, H.: Chemistry of phosphorus insecticides. Ann. appl. Biol. 36, 156–159 (1949).
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).
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).
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).
Cohen, J. A., and C. H. Posthumus: The mechanism of action of anticholinesterases. Acta physiol. pharm. néerl. 4, 17–36 (1958).
Collomp: Les Triions. Bull. d’Information technique et Scientifique. Numéro 23/G, Janvier 1949. Ministère de la Guerre. Section technique de l’armée.
Conley, B. E.: Antagonism of lethal action of parathion by 3-pyridine acetohydroxamic acid methyl iodide. Fed. Proc. 17, 360 (1958).
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.
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.
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).
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).
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).
Craig, F. N., P. D. Bales and H. M. Frankel: Lethality of sarin in a warm environment. J. Pharmacol. 127, 35–38 (1959).
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).
Davies, D. R.: Cholinesterases and the mode of action of some anticholinesterases. J. Pharm. (Lond.) 6, 1–26 (1954).
Davison, A. N.: Return of cholinesterase activity in the rat after inhibition by organo-phosphorus compounds. Biochem. J. 54, 583–590 (1953).
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).
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).
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).
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).
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).
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).
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).
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).
W. B. W. Deichmann, and R. Rasoczy: Toxicity and mechanism of action of Systox. A.M.A. Arch. industr. Hlth 11, 324–331 (1955).
Dickinson, B. C.: Ethion, a promising new acaricide and insecticide. J. econ. Ent. 51, 354–357 (1958).
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).
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).
Dirnhuber, P., and H. Cullumbine: The effect of anticholinesterase agents on the rats blood pressure. Brit. J. Pharmacol. 10, 12–15 (1955).
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).
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).
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.
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).
Dounn, J., and K. P. Dubois: Toxicity and anticholinesterase action of tetra-n-propyl dithionopyrophosphate. J. Pharmacol. 106, 382 (1952).
Dubois, K. P., and J. M. Coon: Toxicology of organic phosphorus-containing insecticides to mammals. Arch. industr. Hyg. 6, 9–13 (1952).
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).
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).
K. P.Dubois, J. Douu and J. M. Coon:The cholinergic action of octamethyl pyrophosphoramide (OMPA). J. Pharmacol. 98, 6–7 (1950).
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).
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).
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).
Dunn, C. L.: Determination of 2,3-p-dioxanedithiol S,S-bis(O,0-diethyl phosphorodithioate). J. Agric. Food Chem. 6, 203–209 (1958).
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.
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).
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).
Dybing, O., and E. Sognen: Hyperglycaemia in rats after diazinon and other cholinesterase inhibitors. Acta pharmacol. 14, 231–235 (1958).
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.
Enander, I.: Experiments with methyl-fluoro-phosphorylcholine-inhibited cholinesterase. Acta Chem. scand. 12, 780–781 (1958).
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).
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).
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).
Fiszer, B., J. Michalski and J. Wieczobkowski: Roczniki Chem. 27, 482 (1953).
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).
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).
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.
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).
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).
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).
Freak, D. E. H.: Chemistry of the pesticides, p. 82. New York: D. van Nostrand Co. Inc. 1955.
Fredriksson, T.: Pharmacological properties of methylfluorophosphorylcholines. Two synthetic cholinergie drugs. Arch. int. Pharmacodyn. 113, 101–113 (1957).
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).
Fredriksson, T. Further studies on fluoro-phosphorylcholines. Pharmacological properties of two new analogues. Arch. in Pharmacodyn. 115, 474–482 (1958).
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).
Fredriksson, T., and G. Trebling: Reversal of effects on the rat nerve-diaphragm preparation produced by methylfluorophosphorylcholines. Biochem. Pharmacol. 2, 63–67 (1959).
Fredriksson, T., and G. Trebling: Demonstration of direct cholinergic receptor effects of methylfluorophosphorylcholines. Biochem. Pharmacol. 2, 286–289 (1959).
Fredriksson, T., and G. Trebling: Inhibition of cholinesterase with methylfluorophosphoryleholiin and — carbocholine, spontaneous return of activity. J. Biochem. Pharmacol. 3, 184–189 (1960).
French patent 1096341.
Fuxuhar, A.: Parathion poisoning. III. Effect of sulfhydryl compounds and 2-pyridine aldoxime methiodide on parathion poisoning. Okayama Igakkai Zasshi 69, 945–958 (1957).
Fuxuto, T. R., and R. L. Metcalf: Manuscript submitted to J. Agric. Food Chem. 1954. See Agr. Chem. 9, 130 (1954).
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).
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).
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).
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).
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).
Gage, J. C.: A cholinesterase inhibitor derived from 0,0-diethyl O-p-nitrophenyl thiophosphate in vivo. Biochem. J. 54, 426–430 (1953).
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.
Gardiner, J. E., and B. A. Kum: I The mammalian metabolism of bis(dimethylamino)phosphorous anhydride (Schradan). Biochem. J. 51, 78–85 (1952).
Gasser, R.: Expériences dans la lutte contre les araignées rouges avec de nouveaux acaricides. III. Int. Congr. Phytopharmacy, Paris, 1952, p. 51.
Gasser, R.: Über ein nues Insektizid mit breitem Wirkungsspektrum. Z. Naturforsch. 8 B, 225 to 232 (1953).
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).
Gnosh, R.: Phosphorodithioates. Brit. Pat. 783,281, Sept. 18, 1957.
Gnosh, R., and J. F. Newman: A new group of organophosphorus pesticides. Chem. and Ind. 1955, p. 118, Jan. 1929.
Giang, P. A.: A bibliography of systemic insecticides. U.S. Dept. of Agriculture, Agricultural Research Service Ent. Research Branch E-874, 1954.
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).
Gilman, A.: The effects of drugs on nerve activity. Ann. N. Y. Acad. Sci. 47, 549–558 (1946).
Goldman, H., and M. Teitel: Malathion poisoning in a 34 month-old child following accidental ingestion. J. Pediat. 52, 76–81 (1958).
Gothelf, B., A. G. Karczmar and K. Blachut: Interaction of bisquaternary and phosphonate anticholinesterases. Fed. Proc. 17, 372 (1958).
Green, A. L.: The kinetic basis of organophosphate poisoning and its treatment. Biochem. Pharmacol. 1, 115–128 (1958).
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).
Grob, D., and A. M. Harvey: The effects and treatment of nerve gas poisoning. Amer. J. Med. 14, 52–63 (1953).
Grob, D., and A. M. Harvey: Effects in man of the anticholinesterase compound sann (isopropyl methyl phosphonofluoridate). J. clin. Invest. 37, 350–368 (1958).
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).
Gysin, H.: Sur un nouveau groupe de substances insecticides. III. Int. Congr. Phytopharmacy, Paris, 1952, p. 40.
Gysin, H.: Some new insecticides. Chimia 8, 205–210, 221–228 (1954).
Gysin, H., u. A. Margot: DBP. 910,652 v. 20. 4. 1952.
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).
Hall, S. A., and M. Jacobson: Hexaethyl tetraphosphate and tetraethyl pyrophosphate. Industr. Engng Chem. 40, 694–699 (1948).
Hanzal, R. F., H. J. Horn and L. W. Hazleton: Anticholinesterase activity of parathion and malathion. Fed. Proc. 13, 363–364 (1954).
Hardy, E. E., and G. M. Kosolapoff: U.S. Pat. 1946. 2, 409, 039.
Hartley, G. S.: Unpublished experiments. Pest Control, Ltd., Cambridge.
Hartley, G. S.: Brit. Pat. 688, 766, 1949.
Hartley, G. S.: Congress abstracts, III. Int. Congr. Phytopharmacy Paris 1952.
Haste, A., and M. Bargar: Prispevok k. farmakodynamike Dipterex (Beitrag zur Pharmakodynamik des Insektizids Dipterex). Biologia (Bratislava) 13, 428–439 (1958).
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).
Hazifton, L. W., and E. G. Holland: Toxicity of Malathion. A.M.A. Arch. industr. Hyg. 8, 399 405 (1953).
Healy, J. K.: Ascending paralysis following malathion intoxication: a case report. Med. J. Aust. 46, 765 (1959).
Heap, R., and B. C. Saunders: Esters containing phosphorus. Part VII. Substituted diaminofluorophosphine oxides. J. chem. Soc. 1948, 1313–1316.
Heath, D. F.: Reactions of ethylthioethyl 0,0-dimethyl phosphorothioates in water. J. chem. Soc. 1958, 1643–1651.
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).
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).
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).
Hecht, G., u. W. Wirth: Zur Pharmakologie der Phosphorsäureester. Naunyn-Schmiedeberg’s Arch. exp. Path. Pharmak. 211, 264–277 (1950).
Henglein, A., u. G. Schrader: Zur Kenntnis der Isomerie-Erscheinungen bei den System-Insektiziden „Systox“ und „Metasystox”. Z. Naturforsch. 10 b, Heft 1 (1955).
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).
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).
Hewitt, R., A. Brebbia and E. Waletsky: Carbamoyl alkyl phosphorodithioates as chemotherapeutic agents. J. econ. Ent. 51, 126–131 (1958).
Heymans, C., A. Pochet et H. VAN Houtte: Contributions it la pharmacologie du Sarin et du Tabun. Arch. int. Pharmacodyn. 104, 293–332 (1956).
Hilgetag, G., u. G. Lehmann: Optisch aktive Thiophosphate. J. prakt. Chem. 8, 224 bis 234 (1959).
Hobbiger, F.: The inhibition of cholinesterases by 3-(diethoxyphosphinyloxy)-N-methylquinolinium methylsulphate and its tertiary base. Brit. J. Pharmacol. 9, 159–165 (1954a).
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.
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).
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).
Hofmann, A. W.: Weitere Beobachtungen über die Phosphinsäuren. Ber. 6, 303–308 (1873).
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).
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).
Holmstedt, B.: Pharmacology of organophosphorus cholinesterase inhibitors. Pharm. Rev. 11, 567–688 (1959).
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).
Holtz, P., u. E. Westerman: Giftung und Entgiftung von Parathion und Paraoxon. Naunyn-Schmiedeberg’s Arch. exp. Path. Pharmak. 237, 211–221 (1959).
Hopf, H. S., and R. T. Taylor: Role of cholinesterase in insecticidal action. Nature (Lond.) 182, 1381–1382 (1958).
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).
Hoskin, F. C. G.: The enzymatic hydrolysis products of sarin. Canad. J. Biochem. 34, 75–79 (1956).
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).
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.
Iwamoto, T., and M. Taga: Effects of methylparathion on the cow and its distribution in the body. Igaku to Seibutsugaku 50, 54–57 (1956).
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).
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).
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).
The mechanism of reaction between esterases and phosphorus-con- taining anti-esterases. Disc. Faraday Soc. 20, 134–142 (1955).
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).
Jean, H.: Esters et sels de la choline et de quelques acides dérivés du phosphore. Bull. Soc. chim. Fr. 1957, 783–786.
Jewell, H. A., and R. A. Lehman: Pharmacology of phospholine iodide-an alkyl phosphothiocholine. Fed. Proc. 17, 381 (1958).
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).
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).
Jung, O.: Toxikologie des Dithiophosphorsäureesters Azethion. Arch. Tox. 16, 341–345 (1957).
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).
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).
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).
Ketelaar, J. A. A.: Abstr. II. Int. Congr. Crop Protection, 1949.
Ketelaar, J. A. A., and J. E. Hellingman: Chemical studies on insecticides. Analyt. Chem. 23, 646–650 (1951).
Ktby, B. A.: Alkyl Fluorophosphonates and Related Compounds. Research 2, 417–422 (1949).
Ktby, B. A., and M. Kelby: The toxicity of alkyl fluorophosphonates in man and animals. Brit. J. Pharmacol. 2, 234–240 (1947).
Kilpatrick, M. L., and M. Kilpatrick: The hydrolysis of diisopropyl fluophosphate. J. phys. Chem. 53, 1371–1384 (1949).
Kilpatrick, M. L., and M. Kilpatrick: A mechanism for the hydrolysis of diisopropyl fluophosphate. J. phys. Chem. 53, 1385–1397 (1949).
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).
Klimmer, O. R., u. W. Pfaff: Vergleichende Untersuchungen über die Toxicität organischer Thiophosphorsäureester. Arzneim.-Forsch. 5, 626–630 (1955).
Klotzsche, C.: Zur Toxikologie neuerer insektizider Phosphorsäureester. Arzneim.Forsch. 5, 436–439 (1955).
Klotzsche, C.: Neue Insektizide Phosphor-und Phosphorsäureester. Nachrbl. deutsch. Pflanzenschutzdienst 10, 60 (1958).
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).
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).
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).
Koelle, G. B., and A. Gilman The chronic toxicity of diisopropyl fluorophosphate (DFP) in dogs, monkeys and rats. J. Pharmacol. 87, 435–448 (1946).
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).
Koll, W.: Personal communication. In letter to the author, March 3, 1960.
Kosolapoff, G. M.: Organophosphorus compounds. New York: John Wiley and Sons, Inc.; New York: Chapman & Hall, Ltd., 1950.
Kovache, H., H. Jean and G. Garnier: Étude de quelques composés organiques du phosphore. Chim et Industr. 64, 287–299 (1950).
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).
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).
Lange, W.: Fortschritte auf dem Gebiete der Darstellung und Verwendung von Fluorverbindungen. Chem. Ztg. 59, 393 (1935).
Lange, W.: Personal letter to the author. April 7, 1952.
Lange, W.:, u. G. vox Krueger: Über Ester der Monofluorphosphorsäure. Ber. dtsch. chem. Ges. 65, 1598–1601 (1932).
Larsson, L.: The hydrolysis of dimethylamido-ethoxyphosphoryl cyanide (Tabun). Acta chem. scand. 7, 306–314 (1953).
Larsson, L.: The alkaline hydrolysis of isopropoxy-methyl-phosphoryl fluoride (Sarin) and some analogues. Acta chem. scand. 11, 1131–1142 (1957).
Larsson, L.: Studies on the chemical reactivity of organic phosphorus compounds. Diss. Svensk kem. Tidskr. 70, 405 427 (1958).
Larsson, L. B. Holmstedt and E. Tjus: Some considerations regarding the nomenclature of organic phosphorus compounds. Acta chem. scand. 8, 1563–1569 (1954).
Lendle, L.: Personal communication (1959).
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).
Locker, A., u. H. Siedek: Über Aktivierung von Cholinesterasen durch Alkylphosphate in vivo. Experientia (Basel) 8, 146–148, 302–303 (1952).
Locker, A., u. H. Siedek: Die Wirkung von Alkylphosphaten auf Gewebsatmung und Cholinesteraseaktivität. Z. ges. exp. Med. 119, 314–326 (1952).
Lorenz, W.:Farbenfabriken Bayer. DBP. 927, 270.
Lorenz, W.: Insecticidal phosphonic ester. U.S. Pat. 2, 701, 225.
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).
Louloudes, S. J., J. N. Kaplanis and C. C. Roan: The synthesis of radioactive Diazinon using 1332. J. org. Chem. 21, 685–686 (1956).
Mackworth, J. F., and E. C. Webb: The inhibition of serum cholinesterase by alkyl fluorophosphonates. Biochem. J. 42, 91–95 (1948).
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).
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).
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).
Martin, H.: Guide to chemicals used in crop protection. Canad. Dept. agric. Bull., 3rd Ed., October 1957, p. 136.
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).
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
Mccommns, H., B. C. Saunders and G. J. Stacey: Esters containing phosphorus. Part III. J. chem. Soc. 1945, 921–922.
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).
Mclvoa, R. A., G. D. Mccarthy and G. A. Grant: Preparation and toxicity of some alkyl thiopyrophosphates. Canad. J. Chem. 34, 1819–1832 (1956).
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).
Metcalf, R. L.: Organic insecticides. Their chemistry and mode of action. New York and London: Interscience Publishers 1955.
Metcalf, R. L. ed.: Advances in pest control research. Vol. 1. New York and London: Interscience Publishers 1957.
R. L.Metcalf, T. R. Fuguto and R. B. March:Plant metabolism of dithio-Systox and Thimet. J. econ. Ent. 50, 338–345 (1957).
R. L.Metcalf: Toxic action of Dipterex and DDVP to the house fly. J. econ. Ent. 52, 44 49 (1959).
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).
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).
R. L.Metcalf,and R. B. March: The isomerization of organic thionophosphate insecticides. J. econ. Ent. 46, 288–294 (1953).
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).
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).
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.
Michaelis, C. A. A.: Über die organischen Verbindungen des Phosphors mit Stickstoff. Liebigs Ann. Chem. 326, 129–258 (1903).
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).
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).
Moyle, C. L.(to The Dow Chemical Co.): U.S. Patent 2,599–516 (June 3, 1952 ).
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).
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).
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).
Murrhy, S. D., and K. P. Dubois: Inhibitory effect of dipterex and other organic phosphates on detoxification of malathion. Fed. Proc. 17, 397 (1958).
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).
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).
Myers, D. K.: Studies on selective esterase inhibitors. Thesis, pp. 97. Amsterdam 1954.
Myers, D. K.: Neue chemische Kampfstof fe. Protar 16, 131–135 (1950).
Nylén, P.: Studien über organische Phosphorverbindungen. Diss., Uppsala 1930.
Obrien, R. D.: The inhibition of cholinesterase and succinoxidase by malathion and its isomer. J. econ. Ent. 49, 484–490 (1956).
Obrien, R. D.: Properties and metabolism in the cockroach and mouse of malathion and malaoxon. J. econ. Ent. 50, 159–164 (1957).
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).
Obrien, R. D.: Effect of ionization upon penetration of organophosphates to the nerve cord of the cockroach. J. econ. Ent. 52, 812–816 (1959).
Obrien, R. D., G. D. Thorn and R. W. Fisher: New organophosphate insecticides developed on rational principles. J. econ. Ent. 51, 714–718 (1958).
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).
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).
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.
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).
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).
Paulet, G.: Nouvelle contribution à l’étude de l’action pharmacologique du tétraéthylpyrophosphate (TEPP). Arch. hit. Pharmacodyn. 97, 157–185 (1954).
Paulet, G.: Activité cholinestérasique et fonctionnement des centres respiratoires. J. Physiol. (Paris) 48, 915–936 (1956).
Perkow, W.: Die Insektizide. 1. Aufl. Heidelberg: Alfred Hüthig 1956.
Petty, C. H.: Organic phosphate insecticide poisoning. Residual effects in two cases. Amer. J. Med. 24, 467 (1958).
Pianka, M.: Organophosphorus compounds. I. Interaction of organic phosphorohalogenides with solid alkalis A new synthesis of Schradan. J. appl. Chem. 5, 109–120 (1955).
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).
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).
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).
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).
Radeleff, R. D., and G. T. Woodward: Toxicological studies of Dow ET-57 in cattle and sheep. J. econ. Ent. 50, 249–251 (1957).
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 ).
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.
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).
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).
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).
Rosenberg, P., and J. M. Coon: Potentiation between cholinesterase inhibitors. Fed. Proc. 17, 406 (1958).
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).
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).
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).
Saunders, B. C.: Phosphorus and fluorine. The chemistry and toxic action of their organic compounds. Cambridge: University Press 1957.
Saunders, B. C., and G. J. Stacey: Esters containing phosphorus. Part IV. Diisopropyl fluorophosphonate. J. them. Soc. 1948, 695–699.
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.
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).
Schall, A.: Über die Einwirkung von Phosphoroxybromid auf sek. a liphatische Amine Dissert. Rostock 1898; Liebigs Ann. Chem. 326, 182 (1903).
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).
Schrader, G.: Belgian Patent 556,009.
Schrader, G.: DBP. 720,577.
Schrader, G.: DBP. 918,603.
Schrader, G.: DBP. 814,297 v. 2. 10. 1948.
Schrader, G.: DBP. 881,194 v. 31. 7. 1951.
Schrader, G.: DBP. 921,870 v. 3. 5. 1952.
Schrader, G.: DAS. 10,101,960 v. 13. 10. 1955.
Schrader, G. and H. Kükenthal: DBP. 918,603 v. 5. 8. 1941.
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.
Schrader, G. and W. Lorenz: DBP. 917,668 v. 2. 8. 1952.
Schrader, G: BIOS Final Report, 1947, p. 714.
Schrader, G.: Organische Phosphor-Verbindungen als neuartige Insektizide (Auszug). Angew. Chem. 62, 471–473 (1950).
Schrader, G.: Die Entwicklung neuer Insektizide auf Grundlage von organischen Fluor-und Phosphorverbindungen. Monographie No. 62, 2. Aufl. Weinheim: Verlag Chemie 1952.
Schrader, G. Chiorothion, a new relatively nontoxic insecticide from the series of the thiophosphoric acid esters. Angew. Chem. 66, 265–267 (1954).
Schrader, G. Die insektiziden Phosphorsäureester. Angew. Chem. 69, 86–90 (1957).
Scott, M. J.: The effects of anticholinesterases upon the spleen of the dog. J. Physiol. 139, 489–496 (1957).
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.
South African Patent 1748/55.
Spencer, E. Y., R. D. Obrien and R. W. White: Permanganate oxidation products of Schradan. J. Agric. Food Chem. 5, 123–127 (1957).
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).
Tahmeun, L.-E.: Dialkoxy-phosphorylthiocholines, alkoxy-methyl-phosphorylthiocholines and analogous choline esters. Acta chem. scand. 11, 1340–1349 (1957).
Tahmeun, L.-E.: Methyl-fluoro-phosphorylcholines. Acta chem. scand. 11, 859–865 (1957).
Tahmeun, L.-E.: Choline esters; substrates and inhibitors of cholinesterases. Svensk kern. Tidskr. 70, 157–181 (1958).
Tahmeun, L.-E.: Organophosphorylcholines and cholinesterases. Ark. kemi 12, 287–298 (1958).
Tibbling, G.: Unpublished.
Tolkmrrh, H.: Electron group polarizability and molecular properties of organophosphorus compounds. Ann. N. Y. Acad. Sci. 79, 187–231 (1959).
Topley, B.: Insecticidal phosphorus compounds. . 1950, Dec. 30, 859–868.
Toy, A. D. F.: The preparation of tetraethyl pyrophosphate and other tetraalkyl pyrophosphates. J. Amer. chem. Soc. 70, 3882–3886 (1948).
Toy, A. D. F.: Tetraethyl dithionopyrophosphate and related tetraalkyl dithionopyrophosphates. J. Amer. chem. Soc. 73, 4670–4674 (1951).
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).
Tuthill, J. W. G.: Malathion poisoning. New Engl. J. Med. 258, 1018–1019 (1958).
U.S. Pat. 2,503,390.
U.S. Pat. 2,640,847; 2,597,534.
U.S. Pat. 2,685,552.
U.S. Pat. 2,759,010; D.B.P. 947,369.
U.S. Pat. 2,761,806.
U.S. Pat. 2,833,805 and 2,725,328; 2,815,350.
Valade ET Salle: Apercu sur les nouveaux toxiques de guerre. Rev. vêt. Milit. 3, 377–385 (1948).
Valters, M. N. I.: Malathion intoxication. Med. J. Aust. 44, 876–880 (1957).
Vandekar, M.: The toxic properties of demeton-methyl (Metasystox) and some related compounds. Brit. J. Ind. Med. 15, 158–167 (1958).
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).
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).
van Wazer, J. R.: Phosphorus and its compounds. Interscience publ. New York 1958.
Webb, E. C.: The biochemical reactions of chemical warfare agents. Biochem. Soc. Symp., No. 2, pp. 50–60. Cambridge 1948.
Wescoe, W. C., and W. F. Biker jr.: The pharmacology of anti-curare agents. Ann N. Y. Acad. Sci. 54, 438–459 (1951).
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).
Wirth, W.: Zur Pharmakologie der Phosphorsäureester. Diäthyl-p-nitrophenylphosphat. (“Mintacol”). Naunyn-Schmiedeberg’s Arch. exp. Path. Pharmak 207, 547–568 (1949).
Wirth, W.: Zur Pharmakologie der Phosphorsäureester. Diäthylthiophosphorsäureester des Athylthioglykol („Systox-Wirkstoff“). Naunyn-Schmiedeberg’s Arch. exp. Path. Pharmak. 217, 144 152 (1953).
Wirth, W.: Zur Wirkung System-insecticider Phosphorsäure-Ester im Warmblüter-Stoffwechsel. Naunyn-Schmiedeberg’s Arch. exp. Path. Pharmak. 234, 352–363 (1958).
Wollenberg, O.: Kolorimetrische Bestimmung des Insektizides „Gusathion“-„Bayer 17147”. Angew. Chem. 68, 581 (1956).
Wollenberg, O., u. G. Schrader: Neuer spezifischer Nachweis des Insektizides „Bayer 17147“ („Gusathion”). Angew. Chem. 68, 41 (1956).
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).
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).
Yip, G., and J. W. Cook: Malathionase. III. Substrate specificity studies. J. Ass. off. agric. Chem. 42, 405–407 (1959).
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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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