Cycloprothrin insecticide publications

The following publications detail the work involved in the development of CSIRO’s Cycloprothrin – the first designer insecticide.

Patents

Holan G, Walser RA, Elmes BC, 1989, ‘New arthropodicides’, U.S. Patent Number 4,849,450.

Holan G, Rihs K, Johnson WMP, 1988, ‘Oxime insecticides’, U.S. Patent Number 4,753,960.

Holan G, Walser RA, 1985, ‘Insecticidal ester enantiomers’, U.S. Patent Number 4,540,710.

Holan G, Johnson WMP, 1984, ‘Insecticidal oximes’, U.S. Patent Number 4,474,815.

Holan G, O’Keefe DF, 1983, ‘Pentafluorobenzyl esters’, U.S. Patent Number 4,390,715.

Holan G, Walser RA, 1983, ‘Insecticidal ester enantiomers’, U.S. Patent Number 4,391,820.

Holan G, O’Keefe DF, 1982, ‘Insecticidal esters’, U.S. Patent Number 4,355,042.

Holan G, O’Keefe DF, 1982, ‘Insecticidal esters’, U.S. Patent Number 4,348,409.

Holan G, O’Keefe DF, 1982, ‘Insecticidal esters’, U.S. Patent Number 4,339,458.

Holan G, Walser RA, 1982, ‘process of making phenylacrylic esters’, U.S. Patent Number 4,309,350.

Holan G, Walser RA, 1981, ‘Insecticidal 1-(2-naphthyl)cyclobutane carboxylate’, U.S. Patent Number 4,277,490.

Holan G, Walser RA, 1981, ‘Insecticidal esters’, U.S. Patent Number 4,262,014.

Holan G, O’Keefe DF, 1980, ‘Insecticidal esters’, U.S. Patent Number 4,235,926.

Holan G, Walser RA, 1980, ‘Insecticidal esters’, U.S. Patent Number 4,220,591.

Key publications

Holan G, 1984, ‘A quest for selective toxicity in the synthesis of insecticides’, Chemistry in Australia, 51: 185-190.

Holan G, Johnson WMP, Rihs K, Virgona CT, 1984, ‘Insecticidal Isosteres of DDT-Pyrethroid Structures’, Pestic. Sci., 15: 361-368.

Holan G, Poppleton BJ, Spurling TH, Virgona CT, 1980, ‘Insects sensory nerve potentials: effects of insecticides’, Insect Neurobiology and Pesticide Action, Proc. Neurotox.’79, Soc. Chem. Industry, pp.73-78.

Farley JM, Narahashi T, Holan G, 1979, ‘The Mechanism of action of a DDT analog on the crayfish neuromuscular junction’, Neurotoxicology, 1: 191-207.

Holan G, O’Keefe DF, Virgona C, Walser R, 1978, ‘Structural and biological link between pyrethroids and DDT in new insecticides’, Nature, 272: 734-736.

Holan G, 1969, ‘New halocyclopropane insecticides and the mode of action of DDT’, Nature, 221: 1025-1029.

Other publications

Holan G, Winkler DA, 1992, ‘QSAR and Rational Design of Insecticides’, In CRC Monograph: Development of Agrochemicals: Structure-Activity Relationships, Fujita T, Draber W (eds), pp.123-145.

Winkler DA, Holan G, Johnson WMP, Jarvis K, 1988, ‘Quantitative structure-activity relationships in insecticidal pyrethroid ethers’, Quant. Struct. Activity Relat., 7: 79.

Hille B, Leibowitz MD, Sutro JB, Schwartz JR, Holan G, 1987, ‘State Dependent Modification of Sodium Channels by Lipid-soluble Agonists’, In: Proteins of Excitable Membranes, Hille B, Famrough DM (eds), Society of General Physiologists Series, John Wiley & Sons, New York, Chapter 7, Volume 41.

Leibowitz MD, Schwartz JR, Holan G, Hille B, 1987, ‘Electrophysiological Comparisons of Insecticide and Alkaloid Antagonists of Na Channels’, J. Gen. Physiol., 90: 75-93.

Lummis SCR, Chen Chow S, Holan G, Johnston GAR, 1987, ‘gamma-Aminobutyric acid receptor ionophore complexes: differential effects of deltamethrin, dichlorodiphenyltrichloroethane (DDT), and some novel insecticides in a rat brain preparation’, J. Neurochemistry, 48: 689-694.

Nishimura K, Hirayama K, Kobayashi T, Holan G, 1986, ‘Quantitative structure-activity relationships of insecticidal diphenyldichlorocyclopropanes’, Pesticide Biochem and Physiol., 25: 153-162.

Holan G, Frelin C, Lazdunski M, 1985, ‘Selectivity of action between pyrethroids and combined DDT-pyrethroid insecticides on Na+ influx into mammalian neuroblastoma’, Experientia, 41: 520-522.

Holan G, Johnson WMP, O’Keefe DF, Quint GL, Rihs K, Spurling TH, Walser R, Frelin C, Lazdunski M, Johnston GAR, Chen Chow S, 1985, ‘Multidisciplinary studies in the design of new insecticides’, In: Recent Advances in the Chemistry of Insect Control, Janes NF (ed), The Royal Society of Chemistry, Cambridge, pp.114-132.

Holan G, Johnson WMP, Rihs K, Virgona CT, 1984, ‘A neurophysiological study of DDT-pyrethroid isosteres on the labellar receptor of Lucilia cuprina‘, Pestic. Sci., 15: 637-641.

Nippon Kayaku Co. Ltd., Tokyo, Japan, 1984, ‘Special Publication, NK 8116, GH414, ‘Cycloprothrin’, Properties, Toxicology, Field Trials, Residue Studies’, Japanese Handbook, 115 pages.

Holan G, Johnson WMP, O’Keefe DF, Rihs K, Smith DRJ, Virgona CT, Walser R, Haslam JM, 1983, ‘New aryl-polyfluorocyclobutane insecticides. Chemical and biological studies’, In: IUPAC, Pesticide Chemistry, Human Welfare and Environment, Miyamoto J, Kearney PC (eds), Pergamon Oxford, pp.119-124.

Virgona C, Holan G, Shipp E, Spurling TH, Quint G, 1982, ‘Neurophysiological effects of insecticides on the labellar taste receptors of Lucilia cuprina Wied’, Pestic. Biochem. and Physiol., 18: 169-173.

Johnson WMP, Holan G, 1981, ‘Facile one-pot synthesis of an insecticide intermediate’, Aust. J. Chem., 34: 2461-2463.

Johnson WMP, Holan G, 1981, ‘Synthesis of substituted tetrafluorocyclobutanes. II. Monosubstituted aryl esters’, Aust. J. Chem., 34: 2363-2368.

Johnson WMP, Holan G, 1981, ‘Synthesis of substituted tetrafluorocyclobutanes. I. Disubstituted alkenyl aryl esters’, Aust. J. Chem., 34: 2355-2362.

Wu CH, Oxford GS, Narahashi T, Holan G, 1980, ‘Interaction of a DDT Analog with the sodium channel of lobster axon’, J. Pharmacol. Exp. Ther., 212: 287-293.

Holan G, O’Keefe DF, Rihs K, Virgona CT, 1979, ‘New insecticides, combined DDT-isosteres and pyrethroid structures’, In: Advances in Pesticide Science, Geissbuhler H (ed), Pergamon Press, pp.201-205.

Morton TC, Holan G and Virgona CTF, 1976, ‘Metabolism of 1,1-bis-(p-Ethoxyphenyl)-2-Nitropropane in the Housefly and the Cluster Caterpillar’, Pestic. Biochem. Physiol., 6: 209-214.

Virgona CT, Holan G, Shipp E, 1976, ‘Contact Repellency of Sheep Blowfly Lucilia cuprina Wied’, Pestic. Sci., 7: 72-74.

Holan G 1975, ‘Mode of action of DDT- new aryl-alicyclic and heterocyclic insecticides’, In: Environmental Quality and Safety, Coulston F, Korte F, Thieme G (eds), Stuttgart, pp.359-364.

Holan G, Spurling TH, 1974, ‘Mode of action of DDT analogues: molecular orbital studies’, Experientia, 30: 480-481.

Holan G, Kowala C, Wunderlich JA, 1973, ‘X-Ray Determination of a New Insecticide, 2,2-di-(p-ethoxyphenyl)-3,3-dimethyloxetan’, J. Chem. Soc. Chem. Comm., 2: 34.

Wood JC, Holan G, 1973, ‘1,1-Bis(p-Ethoxyphenyl)-2-nitropropane, A new Insecticide for the Control of Flies on Domestic Animals’, In: Proc 7th British Insecticide and Fungicide Conference, Brighton, UK, pp.273-279.

Holan G, 1971, ‘Rational design of degradable insecticides’, Nature, 232: 644-647.

Holan G, 1971, ‘Rational design of insecticides’, Bull. Wld. Hlth. Org., 44: 355-362.

DeLacy TP, Kennard CHL, Holan G, 1971, ‘X-Ray Crystal structure of a new insecticide: 1,1-di-(p-ethoxyphenyl)-2,2-dimethylpropane’, J. Chem. Soc. D., 16: 930-931.