Evidence for the Existence of Neurotoxic Esterase in Neural and Lymphatic Tissue of the Adult Hen*?

Total Page:16

File Type:pdf, Size:1020Kb

Evidence for the Existence of Neurotoxic Esterase in Neural and Lymphatic Tissue of the Adult Hen*? BmchemscalPharmacology, Vol. 31.No. 6, pp. 1117-1121,1982 00W2952/82/061117-05$03.00/O Printedin GreatBntain. @ 1982Pergamon Press Ltd. EVIDENCE FOR THE EXISTENCE OF NEUROTOXIC ESTERASE IN NEURAL AND LYMPHATIC TISSUE OF THE ADULT HEN*? BENNIE RICHARD DUDEK and RUDY J. RICHARDSONS Toxicology Research Laboratory, Institute of Environmental and Industrial Health, School of Public Health, The University of Michigan, Ann Arbor, MI 48109, U.S.A. (Received 12 January 1981; accepted 31 August 1981) Abstract-Hen brain and spinal cord contain a number of esterases that hydrolyze phenyl valerate (PV). Most of this activity is sensitive to inhibition by micromolar concentrations of paraoxon. Included among the paraoxon-resistant esterases is neurotoxic esterase (NTE), which is inhibited in vivo and in vitro by certain organophosphorus compounds, such as mipafox, which cause delayed neurotoxicity. Since published information on the NTE content of non-neural tissues was heretofore lacking, a comprehensive study was undertaken of the occurrence of this enzyme in tissues of the adult hen (Callus gallus domesticus), the species of choice in the study of organophosphorus-induced delayed neurotoxicity. Complete differential titration curves of PV esterase activity were obtained by preincubation of each tissue homogenate with a wide range of concentrations of paraoxon, a non-neurotoxic compound, plus or minus mipafox, a neurotoxic compound, followed by PV esterase assay. Brain NTE activity was determined to be 2426 + 104 nmoles.min-‘+ (g wet weight)-’ (mean f S.E.M.). Titration of other tissues resulted in the following NTE activities, expressed as percentages of brain NTE activity: spinal cord (21%), peripheral nerve (1.7%), gastrocnemius muscle (O%), pectoralis muscle (O%), heart (14%), liver (O%), kidney (O%), spleen (70%), spleen lymphocytes (26%), and blood lymphocytes (24%). Using an abbreviated procedure, erythrocytes and plasma showed no NTE activity. These results indicate that NTE has limited distribution among the tissues of the adult hen and is present in lymphatic as well as neural tissue. Certain organophosphorus compounds cause a to neurotoxic and non-neurotoxic inhibitors. Prein- delayed degeneration of long axons in peripheral cubation at an appropriate concentration and time nerves and spinal cord of man, fowl, and certain interval with paraoxon (diethyl p-nitrophenyl phos- other species [1,2]. This condition is referred to as phate), a non-neurotoxic compound, inhibits about delayed neurotoxicity. The hen was used in this study 80% of the total PV esterase activity. If mipafox since this is the animal model commonly used in (N,N’-diisopropyl phosphorodiamidofluoridate), a evaluation of delayed neurotoxicity potential of neurotoxic inhibitor, is included in the preincubation organophosphorus compounds [3]. In species sen- medium, an additional lO-17% of the activity is sitive to a single dose of neurotoxic compounds, inhibited. This decrease in activity upon mipafox there is a latent period of 8-14 days before clinical addition represents NTE activity. signs of ataxia and paralysis and histological evidence This study was undertaken to provide criteria for of distal-to-proximal “dying back” of affected axons identification of NTE activity in tissues of the hen appear. An early biochemical event in this neuro- in the form of complete inhibitor titration curves pathy is the phosphorylation and aging of a particular using the substrate phenyl valerate (PV) [8]. Pre- phenyl valerate (PV) hydrolase in nerve tissue known viously, such curves have been presented for hen as neurotoxic esterase (NTE)Q [4-6]. Inhibition of brain using the less sensitive substrate phenyl phen- hen brain NTE following dosing with neurotoxic ylacetate (PPA) [4] and, more recently, for human organophosphorus compounds is highly correlated brain using PV [9]. It was of interest to rigorously with the production of delayed neurotoxicity [7]. determine whether this enzyme had exclusive local- The NTE assay [5] is based on the differential ization in neural tissue in a given species or whether sensitivity of PV esterases in hen brain homogenate its distribution was more widespread. MATERIALSAND METHODS * This work formed a segment of the Ph.D. dissertation of B. R. D. and was presented in part at the Seventeenth Animals. Spent White Leghorn hens, 1 to 1.5 years Annual Meeting of the Society of Toxicology, San Fran- of age, weighing 1.5 to 2.0 kg were purchased from cisco, CA, March 12-16, 1978. a local supplier. Hens were housed in stainless steel t This research was supported in part by research grants R805339-01, USEPA, and ES01611-01. NIEHS, and bv a wire cages 0.8 X 0.8 X 0.9m with 1.27cm mesh faculty research grant irom the Horace fi. Rackham School stainless wire floors and were kept at least 2 weeks of Graduate Studies, The University of Michigan. before use; birds were maintained in a $ Author to whom correspondence should be sent. temperature-controlled room on a diet of Purina 0 A more precise name that we would like to suggest is Layena laying mash (Ralston Purina Co., St. Louis, neurotoxicant-sensitive esterase (NTSE). MO) and tap water ad lib. A 12-hr light-dark cycle 1117 1118 B. R. DUDEKand R. J. RICHARDSON was maintained throughout the course of the absolute activity remaining at the higher paraoxon experiment. concentrations, yielded an optimum paraoxon con- Chemicals. Paraoxon (diethyl p-nitrophenyl phos- centration, usually 10-100 PM, for use in the mipafox phate) was purchased from the Sigma Chemical Co. titration. (St. Louis, MO) and was purified as described by The mipafox titration curves were generated by Johnson [lo]. Mass spectra of compound purified by including, in the preincubation medium, paraoxdn this method were identical to published spectra [ll]. at the selected optimum concentration, plus mipafox, PV and mipafox were synthesized and purified as dissolved in Tris-EDTA buffer, over the concentra- described by Johnson [lo]. Phenyl valerate was ana- tion range 0.001 to 1024 ,uM. lyzed for impurities using i.r. spectroscopy and by In the cases of lymphocytes and peripheral nerve, assaying for phenol [12]. Both methods showed PV assay volumes were reduced by factors of 20 and 2, to be pure. Purity of mipafox was verified by melting respectively, to accommodate smaller amounts of point: found, 60-61”; published, 61-62” [lo]. All tissue. other chemicals were analytical reagent grade or the For each tissue studied, at least three complete highest grade commercially available; aqueous sol- titration curves were obtained using each inhibitor. utions were prepared using distilled-deionized Data are presented as means ? S.E.M. water. Tissue preparation. The buffer system used RESULTS throughout for tissue homogenization and hom- ogenate dilution was 50 mM Tris-HC1/2 mM EDTA Panels A and B* of Fig. 1 are the neurotoxic and (pH 8.0,25”). Tissues, except for lymphocytes, were non-neurotoxic inhibitor titration curves for hen kept at ice-bath temperature throughout processing, brain PV esterase activity. They serve to illustrate and were blotted before weighing. Homogenizations were generally done in 6.5 vol. of buffer in a glass-Teflon homogenizer with chamber clearance BRAIN: -PARAOXON of 150-230 ,um, using 15 strokes at 2300 ‘pm. *-+MIPAFOX Since peripheral nerve and spinal cord required lengthy manipulation for removal, these tissues were removed from decapitated hens in a 4” cold room. The peripheral nerve used was the endoneurial com- ponent of the ischiatic nerve; tissue was minced with scissors and homogenized using 30-35 strokes in a glass-Teflon homogenizer and passed through a I I I I I ‘-r--i I , nylon screen (333 pm) (TETKO, Inc., Elmsford, a 7 6 5 4 3 2 NY) stretched over the end of a truncated 10 ml -LOG[INHI6ITOR (Ml] plastic syringe to remove residual connective tissue. Gastrocnemius and pectoralis muscles were minced after removal of the thin collagenous sheaths, passed through a tissue press, homogenized, and passed through a nylon screen (333 ,um) to remove 55, residual collagenous material. \ Leucocytes from minced spleen supernatant frac- 1 tions and from peripheral blood were isolated by ggrc40 BRAIN: centrifugation on Ficoll-Paquem (Pharmacia, Pis- ge I-20 TITRATION WITH MIPAFOX “b---. cataway, NJ) [13,14]. Weighed, pelleted cells were 2 PARAOXON = IO0 PM maintained at room temperature until just before use, at which time they were homogenized in buffer 9 6 7 6 5 4 3 with a siliconized glass-Teflon homogenizer (cham- -LOG [MIPAFOX IMI] ber clearance of 100-150 pm). Cells were quantified Fig. 1. (A) Effects of increasing concentrations of paraoxon on the basis of wet weight. Cells obtained by this alone (0) and of increasing concentrations of mipafox in method were checked for identity and purity using the presence of paraoxon (0) on the hydrolysis of phenyl light (Wright’s stain) [15] and electron microscopy. valerate (PV) by hen brain homogenate. The concentration of paraoxon used in the mipafox titration is indicated on This preparation yielded 2 95% lymphocytes. curve B. (B) Effect of mipafox on the paraoxon-insensitive Differential titrations. The NTE assay was done hydrolysis of phenyl valerate by hen brain homogenate; essentially according to the method described pre- 100% = activity remaining that is insensitive to paraoxon viously [5]. Complete paraoxon titration curves were before addition of mipafox. The concentration of paraoxon generated by varying the paraoxon concentration in used in the mipafox titration is indicated on the graph. the preincubation medium, over the concentration Tissue homogenates were preincubated for 20min with range 0.01 to 1000 PM. For tissues that showed very inhibitors before addition of substrate, whereupon incu- high PV esterase activity at low paraoxon concen- bation was continued for an additional 15 min before stop- trations, it was necessary to use an aliquot of the ping the reaction and analyzing for phenol produced is described in Materials and Methods.
Recommended publications
  • Ortho-Cresyl-Phosphate Poisoning
    J Neurol Neurosurg Psychiatry: first published as 10.1136/jnnp.25.3.234 on 1 August 1962. Downloaded from J. Neurol. Neurosurg. Psychiat., 1962, 25, 234 Toxic polyneuritis in Bombay due to ortho-cresyl-phosphate poisoning D. D. VORA, DARAB K. DASTUR, BEATRIZ M. BRAGANCA, L. M. PARIHAR, C. G. S. IYER, R. B. FONDEKAR, AND K. PRABHAKARAN From Lokmanya Tilak Municipal General Hospital, Sion, Neurology Unit, Indian Council of Medical Research, and Department of Enzyme Chemistry, Indian Cancer Research Centre, Bombay Since 1930 poisoning with ortho-cresyl-phosphate purchased food from the same grocer in their neigh- has been recognized as a cause of peripheral poly- bourhood. He also mentioned that others staying in neuritis (Smith, Elvove, and Frazier, 1930). Ortho- the same locality and consuming mustard oil, but cresyl-phosphate (O.C.P.) is widely used as a purchasing their food from other grocers, were not plasticiser and in the production of heat-stable affected. The examination of the other affected per- lubricating oils. Many cases of industrial poisoning sons revealed identical histories and clinical pictures. with O.C.P. have been reported since then but as a In this group there was no history of gastro-enteritis result of strict precautionary measures it has now or of febrile illness preceding the paralysis. These become a rarity. However, the occasional contamina- patients also asserted that all those who were buying is not uncommon. their food from the same grocer but who were not tion of food with O.C.P. Protected by copyright. Poisoning with O.C.P.
    [Show full text]
  • The Effects of Occupational Exposure to Chlorpyrifos on the Peripheral
    201 Occup Environ Med: first published as 10.1136/oem.2003.008847 on 25 February 2004. Downloaded from ORIGINAL ARTICLE The effects of occupational exposure to chlorpyrifos on the peripheral nervous system: a prospective cohort study J W Albers, D H Garabrant, S J Schweitzer, R P Garrison, R J Richardson, S Berent ............................................................................................................................... Occup Environ Med 2004;61:201–211. doi: 10.1136/oem.2003.008847 Aims: To determine whether chronic occupational exposure to chlorpyrifos at levels associated with various aspects of manufacturing produced a clinically evident or subclinical peripheral neuropathy. Methods: Clinical and quantitative nerve conduction study (NCS) examinations were performed on two occasions on chlorpyrifos manufacturing workers who had measurable chlorpyrifos exposure and a referent group. Baseline evaluations were performed on 53 of 66 eligible chlorpyrifos subjects and on 60 of 74 eligible referent subjects; one-year evaluations were completed on 111 of the 113 subjects evaluated at baseline. Results: Chlorpyrifos and referent groups differed significantly in measures of 3,5,6 trichloro-2-pyridinol excretion and plasma butyrylcholinesterase (BuChE) activity, indicating substantially higher exposures See end of article for authors’ affiliations among chlorpyrifos subjects. Few subjects had clinically important neurological symptoms or signs. NCS ....................... results were comparable to control values, and there were no significant group differences in NCS results at baseline, one year, or change over one year. No chlorpyrifos subject fulfilled conventional criteria for Correspondence to: Dr J W Albers, Department confirmed peripheral neuropathy at baseline or one-year examinations. The odds ratios for developing of Neurology, 1C325/ any diagnosable level of peripheral neuropathy among the chlorpyrifos subjects was not increased at 0032 University Hospital, baseline or at one year compared to referents at baseline.
    [Show full text]
  • Enzymatic Degradation of Organophosphorus Pesticides and Nerve Agents by EC: 3.1.8.2
    catalysts Review Enzymatic Degradation of Organophosphorus Pesticides and Nerve Agents by EC: 3.1.8.2 Marek Matula 1, Tomas Kucera 1 , Ondrej Soukup 1,2 and Jaroslav Pejchal 1,* 1 Department of Toxicology and Military Pharmacy, Faculty of Military Health Sciences, University of Defence, Trebesska 1575, 500 01 Hradec Kralove, Czech Republic; [email protected] (M.M.); [email protected] (T.K.); [email protected] (O.S.) 2 Biomedical Research Center, University Hospital Hradec Kralove, Sokolovska 581, 500 05 Hradec Kralove, Czech Republic * Correspondence: [email protected] Received: 26 October 2020; Accepted: 20 November 2020; Published: 24 November 2020 Abstract: The organophosphorus substances, including pesticides and nerve agents (NAs), represent highly toxic compounds. Standard decontamination procedures place a heavy burden on the environment. Given their continued utilization or existence, considerable efforts are being made to develop environmentally friendly methods of decontamination and medical countermeasures against their intoxication. Enzymes can offer both environmental and medical applications. One of the most promising enzymes cleaving organophosphorus compounds is the enzyme with enzyme commission number (EC): 3.1.8.2, called diisopropyl fluorophosphatase (DFPase) or organophosphorus acid anhydrolase from Loligo Vulgaris or Alteromonas sp. JD6.5, respectively. Structure, mechanisms of action and substrate profiles are described for both enzymes. Wild-type (WT) enzymes have a catalytic activity against organophosphorus compounds, including G-type nerve agents. Their stereochemical preference aims their activity towards less toxic enantiomers of the chiral phosphorus center found in most chemical warfare agents. Site-direct mutagenesis has systematically improved the active site of the enzyme. These efforts have resulted in the improvement of catalytic activity and have led to the identification of variants that are more effective at detoxifying both G-type and V-type nerve agents.
    [Show full text]
  • Environmental Health Criteria 63 ORGANOPHOSPHORUS
    Environmental Health Criteria 63 ORGANOPHOSPHORUS INSECTICIDES: A GENERAL INTRODUCTION Please note that the layout and pagination of this web version are not identical with the printed version. Organophophorus insecticides: a general introduction (EHC 63, 1986) INTERNATIONAL PROGRAMME ON CHEMICAL SAFETY ENVIRONMENTAL HEALTH CRITERIA 63 ORGANOPHOSPHORUS INSECTICIDES: A GENERAL INTRODUCTION This report contains the collective views of an international group of experts and does not necessarily represent the decisions or the stated policy of the United Nations Environment Programme, the International Labour Organisation, or the World Health Organization. Published under the joint sponsorship of the United Nations Environment Programme, the International Labour Organisation, and the World Health Organization World Health Orgnization Geneva, 1986 The International Programme on Chemical Safety (IPCS) is a joint venture of the United Nations Environment Programme, the International Labour Organisation, and the World Health Organization. The main objective of the IPCS is to carry out and disseminate evaluations of the effects of chemicals on human health and the quality of the environment. Supporting activities include the development of epidemiological, experimental laboratory, and risk-assessment methods that could produce internationally comparable results, and the development of manpower in the field of toxicology. Other activities carried out by the IPCS include the development of know-how for coping with chemical accidents, coordination
    [Show full text]
  • Recommended Classification of Pesticides by Hazard and Guidelines to Classification 2019 Theinternational Programme on Chemical Safety (IPCS) Was Established in 1980
    The WHO Recommended Classi cation of Pesticides by Hazard and Guidelines to Classi cation 2019 cation Hazard of Pesticides by and Guidelines to Classi The WHO Recommended Classi The WHO Recommended Classi cation of Pesticides by Hazard and Guidelines to Classi cation 2019 The WHO Recommended Classification of Pesticides by Hazard and Guidelines to Classification 2019 TheInternational Programme on Chemical Safety (IPCS) was established in 1980. The overall objectives of the IPCS are to establish the scientific basis for assessment of the risk to human health and the environment from exposure to chemicals, through international peer review processes, as a prerequisite for the promotion of chemical safety, and to provide technical assistance in strengthening national capacities for the sound management of chemicals. This publication was developed in the IOMC context. The contents do not necessarily reflect the views or stated policies of individual IOMC Participating Organizations. The Inter-Organization Programme for the Sound Management of Chemicals (IOMC) was established in 1995 following recommendations made by the 1992 UN Conference on Environment and Development to strengthen cooperation and increase international coordination in the field of chemical safety. The Participating Organizations are: FAO, ILO, UNDP, UNEP, UNIDO, UNITAR, WHO, World Bank and OECD. The purpose of the IOMC is to promote coordination of the policies and activities pursued by the Participating Organizations, jointly or separately, to achieve the sound management of chemicals in relation to human health and the environment. WHO recommended classification of pesticides by hazard and guidelines to classification, 2019 edition ISBN 978-92-4-000566-2 (electronic version) ISBN 978-92-4-000567-9 (print version) ISSN 1684-1042 © World Health Organization 2020 Some rights reserved.
    [Show full text]
  • NMP-Free Formulations of Neonicotinoids
    (19) & (11) EP 2 266 400 A1 (12) EUROPEAN PATENT APPLICATION (43) Date of publication: (51) Int Cl.: 29.12.2010 Bulletin 2010/52 A01N 43/40 (2006.01) A01N 43/86 (2006.01) A01N 47/40 (2006.01) A01N 51/00 (2006.01) (2006.01) (2006.01) (21) Application number: 09305544.0 A01P 7/00 A01N 25/02 (22) Date of filing: 15.06.2009 (84) Designated Contracting States: (72) Inventors: AT BE BG CH CY CZ DE DK EE ES FI FR GB GR • Gasse, Jean-Jacques HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL 27600 Saint-Aubin-Sur-Gaillon (FR) PT RO SE SI SK TR • Duchamp, Guillaume Designated Extension States: 92230 Gennevilliers (FR) AL BA RS • Cantero, Maria 92230 Gennevilliers (FR) (71) Applicant: NUFARM 92233 Gennevelliers (FR) (74) Representative: Cabinet Plasseraud 52, rue de la Victoire 75440 Paris Cedex 09 (FR) (54) NMP-free formulations of neonicotinoids (57) The invention relates to NMP-free liquid formulation comprising at least one nicotinoid and at least one aprotic polar component selected from the group comprising the compounds of formula I, II or III below, and mixtures thereof, wherein R1 and R2 independently represent H or an alkyl group having less than 5 carbons, preferably a methyl group, and n represents an integer ranging from 0 to 5, and to their applications. EP 2 266 400 A1 Printed by Jouve, 75001 PARIS (FR) EP 2 266 400 A1 Description Technical Field of the invention 5 [0001] The invention relates to novel liquid formulations of neonicotinoids and to their use for treating plants, for protecting plants from pests and/or for controlling pests infestation.
    [Show full text]
  • Genomic and Phenotypic Alterations of the Neuronal-Like Cells
    Int. J. Mol. Sci. 2014, 15, 905-926; doi:10.3390/ijms15010905 OPEN ACCESS International Journal of Molecular Sciences ISSN 1422-0067 www.mdpi.com/journal/ijms Article Genomic and Phenotypic Alterations of the Neuronal-Like Cells Derived from Human Embryonal Carcinoma Stem Cells (NT2) Caused by Exposure to Organophosphorus Compounds Paraoxon and Mipafox David Pamies 1,2,3,*, Miguel A. Sogorb 1, Marco Fabbri 2,4, Laura Gribaldo 2, Angelo Collotta 2, Bibiana Scelfo 2, Eugenio Vilanova 1, Georgina Harris 2,3 and Anna Bal-Price 2 1 Bioengineering Institute, Miguel Hernández University, Elche 03202, Alicante, Spain; E-Mails: [email protected] (M.A.S.); [email protected] (E.V.) 2 Institute for Health and Consumer Protection, European Commission Joint Research Centre, Ispra, Varese 21027, Italy; E-Mails: [email protected] (M.F.); [email protected] (L.G.); [email protected] (A.C.); [email protected] (B.S.); [email protected] (G.H.); [email protected] (A.B.-P.) 3 Bloomberg School of Public Health, Johns Hopkins University, CAAT, Baltimore, MD 21205, USA 4 Department of Experimental and Clinical Medicine, University of Insubria, Varese 21100, Italy * Author to whom correspondence should be addressed; E-Mail: [email protected]; Tel.: +1-410-614-4990; Fax: +1-470-614-2871. Received: 14 October 2013; in revised form: 8 December 2013 / Accepted: 17 December 2013 / Published: 9 January 2014 Abstract: Historically, only few chemicals have been identified as neurodevelopmental toxicants, however, concern remains, and has recently increased, based upon the association between chemical exposures and increased developmental disorders.
    [Show full text]
  • Characterization of Neuropathy Target Esterase Using Trifluoromethyl Ketones
    Biochemml Pharmocolog,v, Vol.40. No. 12. pp. 2587-2596. 1990. lloO6-2952/90$3.00+ 0.00 PrintedinGreat Britain. Q 1990Pergamon Press plc CHARACTERIZATION OF NEUROPATHY TARGET ESTERASE USING TRIFLUOROMETHYL KETONES THOMAS C.THOMAS,* ANDRASSZ~KACS,~SSCOTTKOJAS,* BRUCED.HAMMOCK,~~ BARRY W. WILSON/]and MARK G.McNAMEE*~ Departments of *Biochemistry and Biophysics, //Avian Sciences, fEntomology, and liEnvironmenta1 Toxicology, University of California, Davis, CA 95616, U.S.A. (Receioed 8 Janunry 1990; accepted 8 June 1990) Abstract-Neuropathy target esterase (NTE) is a membrane-bound carboxylesterase activity which is proposed as the target site in nerve tissue for initiation of organophosphate-induced delayed neuropathy. This activity is identified as phenyl valerate hydrolysis which is resistant to treatment with paraoxon and sensitive to co-incubation with paraoxon and mipafox. NTE preparations were obtained, which did not contain paraoxon-sensitive or mipafox-resistant hydrolases, by selective reconstitution of detergent-solubilized NTE from chick embryo brain into asolectin vesicles during gel filtration. The topography of the catalytic site of NTE was then examined by investigating the inhibition of NTE by a series of 3-alkylthio- and 3-arylthio-l,l,l-trifluoro-propan-2-ones. These trifluoromethyl ketones were found to be rapidly reversible, competitive inhibitors of NTE with I,, values from 1.3 X 1Om4 M to 4.9 x lo-” M. Correlation of Is<, values with octanol/water partition coefficients (Pi. in the range of log P = 1.5 to 5.9, indicated that the optimal lipophilicity for NTE substrates and inhibitors is in the range of log P = 3.0 to 3.4.
    [Show full text]
  • United States Patent (19) 11 3,941,829 Pissiotas Et Al
    United States Patent (19) 11 3,941,829 Pissiotas et al. (45) Mar. 2, 1976 54 N-PHENYL-N'-CARBOPHENOXY FORMAMIDINES 57 ABSTRACT (75) Inventors: Georg Pissiotas, Lorrach, Germany; Phenylformamidines of the formula Dieter Dürr, Bottmingen, Switzerland 4 R3 (73) Assignee: Ciba-Geigy Corporation, Ardsley, R N.Y. R5 NiccH-N / (22 Filed: Dec. 1, 1972 N (21) Appl. No.: 311,058 COOR2 R6 R7 30 Foreign Application Priority Data Dec. 7, 1971 Switzerland....................... 17790/7 wherein R represents hydrogen, alkyl, alkenyl or al Dec. 7, 1971 Switzerland....................... 1779/7 kynyl, R represents a-naphthyl, Jan. 26, 1972 Switzerland......................... 1224/72 Oct. 27, 1972 Switzerland....................... 5729/72 52) U.S. Cl...... 260f471 C; 260/240 G; 260/465 D; 260/470; 260/472; 424/277; 424/278; 424/285; 424/300 (51) int. Cl......................................... C07C 125/06 (58) Field of Search..... 260/471 C, 472, 470, 240 G 56 References Cited or substituted phenyl, FOREIGN PATENTS OR APPLICATIONS wherein the phenyl group is not substituted simulta 890,922 lf 972 Canada neously in the 2-position by a methyl group and in the 2,202,034 | 972 Germany 4-position by a chlorine atom, R. R. R. R. and R. 2,123,001 81972 France represent one or more radicals which are the same or 778,383 7/1972 Belgium different, such as hydrogen or halogen atoms or alkyl, alkoxy, alkylthio, alkenyloxy, alkynyloxy, alkoxycar Primary Examiner-Anton H. Sutto bonyl, CFs, cyano or nitro groups, their process for Assistant Examiner-Michael Shippen the manufacture and their use in pest control.
    [Show full text]
  • Title 農薬の名称 Author(S) 大野, 稔 Citation 防虫科学 (1956), 21(2
    Title 農薬の名称 Author(s) 大野, 稔 Citation 防虫科学 (1956), 21(2): 54-62 Issue Date 1956-05-29 URL http://hdl.handle.net/2433/156936 Right Type Departmental Bulletin Paper Textversion publisher Kyoto University 防 虫 科 学 郡 21 巻-T 雑 録 CommonNaJneSOEPesticidesMino印 OfI y0 ,BoLyu-Kagahu21 , 弘,1956. 13 ・、農 薬 の 名 称 . 大 野 稔 近咋多種多様の良薬の出葺削こより,ややもするとその名称に混乱を来 しそうである。 米国では T. Econ.Ent. , に用ひる殺虫剤の名称は ⅠnterdepartmentalCommitteeofPestControl で公認 された commonname のあるものは・ その名称 を 用ひなlすればな らないこととされて JF_tる。 其の他に, 独 占的でよく知 られた田有名や会社番号名の ものは 大文字をつけて用ひて も よい。 又長い間親 しまれた名称で改名すると混乱する恐れのあるものや, 分子中の原子,原子 団の位置を省略 した短い化学名な どは, そのまま使用 して もよいこととされて居 る。 次 に共等 の朝出剤及び教程の殺菌剤の名称 (下表 ・左仙)を示す。 ComⅡ10JINamesoflnSeCticides NA hLJ.i HT,o BR D EFIyI,mi ・TO.TiITEでIA諾 SDr言霊NATl冨T3Ds .lldrin notlessthan95percentof1 ,2, 3,4,10,10- compourid118 hexachloro l1, 4,4a ,5,8,8a-hexahydr0-1 ,4,5,. 8-dimethanonapbtbalene .lllcthrin dE-2 lally1-41hydroxy-3-methy1-2-cyclopenten- allyll10mOlogofcinerin1 1-oneesterifiedwithamixtureofGisand syntheticpyrethrins ・ tramsdZ-Chrysanthemummonocarboxylicacids ^m.Cy.lnamid 3911 0,0-diethylS-ethylmercaptomethyldithio - pl10Sphate ^m.Cy.lnamid4124 0 -(2-cわlor(I-4-mitropheny l)-0,0 -dimethyl isochlorthion t】liophosphate ^rn.Cyanamid12008 0 ,0-diethyl.S-isopropylmercaptO-methyl dithoplloSphate ^m.Cyammid1200rJ 0,0-diethyl.Sl1Z-PrOpylmercapto一methyl dithiophospbate Am.Cy.lnamid12013 0,0 -diisopropylS-isopropylmercapt0-methyl dithiophosphate ^r.lmite productcontaining2-(p-tert-I)utylphenoxy) compoundSSR isopropy1-1-methylethy 1 2-chloroethyl-sulfitealkylarylsulfite azobenzene
    [Show full text]
  • Is Apis Mellifera More Sensitive to Insecticides Than Other Insects?
    Review Received: 17 February 2010 Revised: 26 May 2010 Accepted: 27 May 2010 Published online in Wiley Online Library: 29 July 2010 (wileyonlinelibrary.com) DOI 10.1002/ps.2001 Is Apis mellifera more sensitive to insecticides than other insects? Melissa C Hardstone and Jeffrey G Scott∗ Abstract BACKGROUND: Honey bees (Apis mellifera L.) are among the most important pollinators in natural and agricultural settings. They commonly encounter insecticides, and the effects of insecticides on honey bees have been frequently noted. It has been suggested that honey bees may be (as a species) uniquely sensitive to insecticides, although no comparative toxicology study has been undertaken to examine this claim. An extensive literature review was conducted, using data in which adult insects were topically treated with insecticides. The goal of this review was to summarize insecticide toxicity data between A. mellifera and other insects to determine the relative sensitivity of honey bees to insecticides. RESULTS: It was found that, in general, honey bees were no more sensitive than other insect species across the 62 insecticides examined. In addition, honey bees were not more sensitive to any of the six classes of insecticides (carbamates, nicotinoids, organochlorines, organophosphates, pyrethroids and miscellaneous) examined. CONCLUSIONS: While honey bees can be sensitive to individual insecticides, they are not a highly sensitive species to insecticides overall, or even to specific classes of insecticides. However, all pesticides should be used in a way that minimizes honey bee exposure, so as to minimize possible declines in the number of bees and/or honey contamination. c 2010 Society of Chemical Industry Supporting information may be found in the online version of this article.
    [Show full text]
  • Our Investigations on Saligenin Cyclic Phos Phorus Esters Have Started
    [Agr. Biol. Chem., Vol. 29, No. 3, p. 243•`248, 1965] Saligenin Cyclic Phosphoramidates and Phosphoramidothionates as Pesticides By Morifusa ETO, Ken KOBAYASHI,_??_ Takeshi KATO,_??_ Kenichi KOJIMA* and Yasuyoshi OSHIMA Department of Agricultural Chemistry, Kyushu University, Fukuoka and *Institute for Agricultural Chemicals, Toa Noyaku Co., Odawara Received October 5, 1964 Several saligenin cyclic phosphoramidates and phosphoramidothionates were synthesized and their pesticidal activities against insects, mites and nematodes were examined. 2- Methylamino-4H-1,3,2-benzodioxaphosphorin-2-oxide and its thiono analog had high acti vities. They were also effective as systemic insecticides. When the size or number of substituent on nitrogen increased, the pesticidal activities decreased. Our investigations on saligenin cyclic phos EXPERIMENTALS phorus esters have started with the finding of Syntheses. the biologically active metabolite of tri-o-tolyl All cyclic phosphoramidates and phosphoramido phosphate.1,2) It has been demonstrated that thionates were synthesized from saligenin and ap methyl phosphate (Salioxon) and methyl phos propriate phosphoramidic dichloride or phosphor amidothioic dichloride by the action of proper phorothionate (Salithion) derivatives in this dehydrogen chloride agent. The reaction of saligenin series have high insecticidal activities.3,4) As with reactive dichloride as monoalkylphosphoramidic some known systemic insecticides" such as dichloride and some others was proceeded by the Schradan (octamethylpyrophosphoramide) and action of tertiary amine such as pyridine (Procedures Mipafox (N, N'-diisopropylphosphorodiamidic Ap and Ap') or triethylamine (Procedure At) in u fluoride) have phosphoramide linkage, it ap cooled condition. Liquid dichloride was usually added peared that systemic insecticidal properties dropwise to the mixture of saligenin and the base would be expected from amidate derivatives in chloroform (Procedures Ap and At).
    [Show full text]