the pesticide manual .pdf

A World Compendium

The Pesticide ManualSixteenth Edition

Supplementary Entries Extended

Editor: C. MacBean

Promoting the science and practice of sustainable crop production

2012 BCPC (British Crop Production Council)All rights reserved. No part of this publication may be reproduced, stored in a retrieval system, or transmitted, in any form or by any means, electronic, mechanical, photocopying, recording or otherwise, without the prior permission of the copyright owner.

British Library Cataloguing in Publication Data. A catalogue record of this book is available from the British Library.

ISBN 978 1 901396 86 7

First published 1968 Seventh edition 1983 Thirteenth edition 2003 Second edition 1971 Eighth edition 1987 Fourteenth edition 2006 Third edition 1972 Ninth edition 1991 Fifteenth edition 2009 Fourth edition 1974 Tenth edition* 1994 Fifth edition 1977 Eleventh edition 1997 Sixth edition 1979 Twelfth edition 2000* The tenth edition incorporated The Agrochemicals Handbook, previously published by The Royal Society of Chemistry.

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All BCPC publications can be purchased from: BCPC Publications, 7 Omni Business Centre, Omega Park, Alton, Hampshire, GU34 2QD, UK Tel +44 (0) 1420 593 200 Fax +44 (0) 1420 593 209 Email: [email protected] Or direct from the BCPC Shop at www.bcpc.org/shop

Disclaimer: Every effort has been made to ensure that all information in this edition of The Pesticide Manual is correct at the time of going to press. However, the editor and the publisher do not accept liability for any error or omission in the content, or for any loss, damage or any other accident arising from the use of the products listed therein. Before handling, storing or using any approved crop protection product, it is essential to follow the instructions on the label.

iii

Supplementary EntriesThese entries include (i) superseded materials, believed to be no longer manufactured, or marketed, for crop protection use; (ii) some materials that are in the public domain and believed to be in late stages of development; and (iii) materials that reached late development but were ultimately not marketed.These entries are short descriptions. For chemical materials, they may include the following information:Sequential entry number.A header name, with an indication of the type of name (such as common name, chemical name, etc.).Chemical Abstracts Service Registry Number (CAS RN).Approved common name (if different from the name in the header, or if other common names have been approved by national bodies).Molecular formula (M.f.).Other names.Code numbers (development codes).The main former product or products.For an explanation of this information see the Guide to Using the Main Entries, p. viii of The Pesticide Manual Sixteenth Edition.It is difficult, in some cases, to be sure whether or not all commercial activity in a substance has ceased; some of these superseded materials are known to be still in use for non-agricultural purposes. The Editor will be grateful for details of any materials in this section that are still in commercial, agricultural use; he can be contacted via the publishers, or at [email protected].


AC 94,377 1

AC 94,377Plant growth regulator

NOMENCLATURE:IUPAC name 1-(4-chloro-1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)cyclohexane-1-carboxamide; 1-phthalimidocyclohexane-1-carboxamideChemical Abstracts name 1-(4-chloro-1,3-dihydro-1,3-dioxo-[2H]-isoindol-2-yl)-cyclohexanecarboxamide CAS RN [51971676] Development codes AC 94,377; CL 94,377 (both Cyanamid) Smiles code NC(=O)C1(CCCCC1)N2C(=O)c3cccc(Cl)c3C2=OPHYSICAL CHEMISTRY: Mol. wt. 306.7 M.f. C15H15ClN2O3 Form White crystalline solid. M.p. 193195 C Solubility In water 30 ppm (25 C). In acetone 5000 mg/kg. Skin and eye Acute percutaneous LD50 for male and female rabbits >2000 mg/kg. Mildly irritating to eyes; non-irritating to skin (male rabbits). Other Non-mutagenic in the Ames test, microbial mutagenicity assay, and host-mediated assay. Details PM12, Entry 3.

N

Cl O

ONH2

O

2

The Pesticide Manual Sixteenth Edition BCPC 2012

acetic acid

ACD 10614; ACD 10435Herbicide

NOMENCLATURE:IUPAC name 1,1,1,7,7,7-hexafluoro-4-methyl-2,6-bis(trifluoromethyl)hept-3-ene-2,6-diol (i) and tautomer 1,1,1,7,7,7-hexafluoro-4-methylene-2,6-bis(trifluoromethyl)heptane-2,6-diol (ii); forming monosodium 1,1,1,7,7,7-hexafluoro-4-methyl-2,6-bis(trifluoromethyl)hept-3-ene-2,6-diolate and monosodium 1,1,1,7,7,7-hexafluoro-4-methylene-2,6-bis(trifluoromethyl)heptane-2,6-diolateChemical Abstracts name 1,1,1,7,7,7-hexafluoro-4-methyl-2,6-bis(trifluoromethyl)-3-heptene-2,6-diol (i) and 1,1,1,7,7,7-hexafluoro-4-methylene-2,6-bis(trifluoromethyl)-2,6-heptanediol (ii) CAS RN [756912] (i); [16202918] (ii); [19493948] monosodium salts Development codes ACD 10 614 (i + ii); ACD 10 435 (monosodium salts)PHYSICAL CHEMISTRY: Mol. wt. 388.2 M.f. C10H8F12O2 Form Monosodium salts form a colourless solid. M.p. 143145 C; monosodium salts >300 C Solubility Practically insoluble in water, benzene, dichloromethane, xylene; soluble in alkali, acetone, diethyl ether, DMF, DMSO, dioxane, bis(2-methoxyethyl) ether. Sodium salt soluble in water, acetone, diethyl ether, dioxane, ethanol; insoluble in benzene, hexane.COMMERCIALISATION:History Herbicide evaluated by Allied Chemical Corp., Agrochemical Division (later Hopkins Agricultural Chemical Co.).APPLICATIONS:Mode of action Selective herbicide. Uses Both the diol and its monosodium salt pre-em. at 2.36.8 kg/ha controlled weeds selectively in cereals, maize, sorghum and soya beans; and post-em. at 2.3 kg/ha in maize, sorghum, soya beans and wheat. Formulation types EC (diol); GR (diol); SP (hydrated sodium salt); WP (diol).MAMMALIAN TOXICOLOGY:Oral Diol: Acute oral LD50 for fasted albino rats 17.8 mg/kg. Monosodium salt: 20.2 mg/kg. Skin and eye Acute percutaneous LD50 for albino rabbits 141 mg/kg. Details PM4, p. 296.

acetic acidHerbicide

See also The Manual of Biocontrol Agents 4th edn entry: 2:151NOMENCLATURE:CAS RN [64197]PRODUCTS:Other products Natures Glory Weed & Grass Killer (Ecoval).TOXICOLOGICAL & ENVIRONMENTAL REVIEWS:EU Rev. Rep. SANCO/2602/08 (2008) EU Status (1107/2009) 2008/127/EC


acrylonitrile 3

acetoproleAcaricide, insecticide, nematicide

NOMENCLATURE:Common name (m) ac(toprole) (F-ISO); acetoprole (BSI, E-ISO)IUPAC name ()-1-[5-amino-1-(2,6-dichloro-,,-trifluoro-p-tolyl)-4-(methylsulfinyl)pyrazol-3-yl]ethanoneChemical Abstracts name 1-[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(methylsulfinyl)-1H-pyrazol-3-yl]ethanone CAS RN [209861585] Development codes RPA 115782PHYSICAL CHEMISTRY: Mol. wt. 400.2 M.f. C13H10Cl2F3N3O2SCOMMERCIALISATION:Manufacturers Rhne-Poulenc

acrylonitrileInsecticide

NOMENCLATURE:Common name acrylonitrile (BSI, E-ISO, F-ISO, ESA, accepted in lieu of a common name)IUPAC name acrylonitrileChemical Abstracts name 2-propenenitrile Other names vinyl cyanide CAS RN [107131] EC no 2034665 Smiles code C=CC#NPHYSICAL CHEMISTRY: Mol. wt. 53.06 M.f. C3H3N M.p. 82 C B.p. 77 C V.p. 1.37 107 mPa (25 C) S.g./density 0.801 (425 C); gaseous, 1.83 (air = 1) Solubility In water ca. 8% (room temperature). Unlimited miscibility with common organic solvents. Stability Readily polymerised, sometimes explosively. Addition of stabilizers is necessary. F.p. 0 C. Mixtures with air having 317% vol./vol. acrylonitrile are flammable.COMMERCIALISATION:History Developed as a fumigant insecticide (The Chemistry of Acrylonitrile) by American Cyanamid Co.APPLICATIONS:Biochemistry Respiratory action similar to that of hydrogen cyanide. Mode of action Fumigant insecticide Uses Fumigant insecticide (ca. 510 g/m3) for the control of pests in living areas and warehouses, machines in milling, baking, and food processing. Formulation types TC.PRODUCTS:Discontinued products VCN* (Stauffer); Ventox* (Detia Degesch).ANALYSIS: In air, by absorption of the fumes in a measured quantity of air in an alkaline solution of laurylmercaptan in isopropanol; the mercaptan is introduced at the double bond. Oxidation of excess mercaptan to the disulfide with iodine solution and back-titration of the unused

4


afidopyropen

iodine or electrophotometric determination (J. Haslam & G. Newlands Analyst, 1955, 80, 50). Residues: cyanogen bromide, formed by the action of bromine (in uv light) on acrylonitrile generated in a nitrogen stream, forms a dye with benzidine-pyridine which can be determined colorimetrically (Man. Pestic. Residue Anal., 120). For gc determination see Anal. Methods Pestic. Plant Growth Regul. 1972, 6, 259260. For spectrophotometric determination of the pyridine-acrylonitrile complex see M. E. Hall & J. W. Stevens (Anal. Chem. 1977, 49, 22772279). Methods reviewed by J. L. Daft in Comp. Anal. Profiles, Chapter 11.TOXICOLOGICAL & ENVIRONMENTAL REVIEWS:EHC 28 (1983). JMPR Evaln. 5 (1965). HSG 1 (1986). ICSC 0092 (2001). CICAD 39 (2002). IARC 71 (1999).MAMMALIAN TOXICOLOGY:IARC Class 2BOral Acute oral LD50 for rats 93 mg/kg. Skin and eye Liquid acrylonitrile permeates through the skin. Inhalation Exposure to air containing 635 and 110 ml/m3 is lethal to rats and dogs, respectively, within 4 hours. ADI/RfD (JMPR) No ADI [1965]; (EPA) RfD 0.01 mg/kg b.w. [1993]. Other It may be a carcinogen. Toxicity Class WHO (a.i.) FM. ECClassification F; R11| R45| T; R23/24/25| Xi; R37/38, R41| R43| N; R51, R53| concn. dep.ECOTOXICOLOGY:Bees Toxicity to bees not significant. Details PM5, p. 3.

afidopyropenInsecticide

NOMENCLATURE:Common name afidopyropen (pa ISO)IUPAC name [(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-(cyclopropylcarbonyloxy)-

O

O

N

O

HO O

O

CH3H2C

H3C

OO

H

CH3

H

OH


AKH-7088 5

1,2,3,4,4a,5,6,6a,12a,12b-decahydro-6,12-dihydroxy-4,6a,12b-trimethyl-11-oxo-9-(3-py-ridyl)-11H,12H-benzo[f]pyrano[4,3-b]chromen-4-yl]methyl cyclopropanecarboxylateChemical Abstracts name [(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-[(cyclopropylcarbonyl)oxy]-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-6,12-dihydroxy-4,6a,12b-trimethyl-11-oxo-9-(3-pyridinyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-4-yl]methyl cyclopropanecarboxylate CAS RN [915972177] Development codes ME5343 Smiles code O=C(OC(C1=CN=CC=C1)=C2)C3=C2O[C@@]([C@@H](O)C4)(C)[C@@]([C@H]3O)([H])[C@]5(C)[C@@]4([H])[C@](C)(COC(C6CC6)=O)[C@@H](OC(C7CC7)=O)CC5PHYSICAL CHEMISTRY: Mol. wt. 593.7 M.f. C33H39NO9

AKH-7088Herbicide

NOMENCLATURE:IUPAC name methyl (EZ)-1-[5-(2-chloro-,,-trifluoro-p-tolyloxy)-2-nitrophenyl]-2-methoxyethylideneamino-oxyacetateChemical Abstracts name methyl [[[1-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenyl]-2-methoxyethylidene]amino]oxy]acetate CAS RN [104459827] Development codes AKH-7088 Smiles code COCC(=NOCC(=O)OC)c1cc(Oc2ccc(cc2Cl)C(F)(F)F)ccc1[N+](=O)[O-]PHYSICAL CHEMISTRY: Mol. wt. 476.8 M.f. C19H16ClF3N2O7 Form Colourless crystals. M.p. 57.758.1 C Solubility In water 1 mg/l (20 C). In dichloromethane >50%, toluene 15% (both 20 C).COMMERCIALISATION:History Discovered in 1984 by Asahi Chemical Industry Co. Ltd. Reported by Y. Hayashi et al. (Proc. Br. Crop Prot. Conf. Weeds, 1989, 1, 5358).APPLICATIONS:Biochemistry (E)- and (Z)- isomers show similar biological activity. Uses Post-emergence control of broad-leaved weeds, including velvetleaf, cockleburs, and Jimson weed, in soya beans, at 0.10.2 kg/ha.MAMMALIAN TOXICOLOGY:Oral Acute oral LD50 for rats 5000 mg/kg. Skin and eye Acute percutaneous LD50 for rats 2000 mg/kg. Moderate skin irritation; non-irritating to eyes (male rabbits). Other Non-mutagenic in the Ames test.

F3C

Cl

O NO2

C

CH2OCH3NOCH2CO2CH3

6


aldimorph

Details PM12, Entry 15.

aldimorphFungicide

FRAC 5, G2; SBI class II, amine: morpholineNOMENCLATURE:Common name aldimorphe ((m) F-ISO); aldimorph (BSI, E-ISO)IUPAC name 4-alkyl-2,5 (or 2,6) -dimethylmorpholine, mixed compounds where the alkyl substituent may be octyl, decyl, dodecyl, tetradecyl or hexadecyl and where the main component is 4-dodecyl-2,6-dimethylmorpholineChemical Abstracts name aldimorph CAS RN [91315150] Development codes B 8243PHYSICAL CHEMISTRY: Mol. wt. 283.5 M.f. C18H37NO (main component) Form Colourless liquid. M.p. 27 to 19 C B.p. 110140 C /0.1 mbar V.p. 5.5 101 mPa (21.8 C) Solubility In water c. 20 mg/l (25 C). Stability Very stable between pH 3 and pH 10. Stable to light. On heating abovec. 60 C, gives a weak brown coloration.COMMERCIALISATION:Manufacturers HermaniaAPPLICATIONS:Biochemistry Ergosterol biosynthesis inhibitor, by inhibition of sterol reduction (sterol-14-reductase) and isomerisation (8 to 7-isomerase). Mode of action Systemic, long-term, also curative action. Absorbed through leaves and roots. Inhibits formation of haustoria in Erysiphe graminis. Uses Controls mildew on spring and winter barley. Formulation types EC.PRODUCTS:Discontinued products Falimorph* (Fahlberg-List).ANALYSIS:Product analysis by acidimetric titration in non-aqueous medium. Residues by extraction wth methanol, transfer to hexane, column chromatographic clean-up on aluminium oxide, and colorimetric determination at 540 nm of coloured substances released by hydrochloric acid from the methyl orange-active ingredient salt.TOXICOLOGICAL & ENVIRONMENTAL REVIEWS:EU Status (1107/2009) Not approved, Commission Regulation 2076/2002.MAMMALIAN TOXICOLOGY:Oral Acute oral LD50 for rats >3000 mice 9700 mg/kg. Skin and eye Dermal LD50 for guinea pigs 1430 mg/kg. Skin irritant. NOEL In 90 d feeding trials on rats, highest dose without activity was 2 mg/kg b.w. daily. ADI/RfD (BfR) 0.01 mg/kg b.w. [1991] Other Possible teratogen.


aldoxycarb 7

ECOTOXICOLOGY:Fish LC50 (96 h) for carp 2.83, salmon 0.38 mg/l. Bees Not toxic to bees.ENVIRONMENTAL FATE:Plants The a.i. content in barley and wheat decreases from 18 mg/kg at application to 0.14 mg/kg after 30 d and 0.1 mg/kg after 45 and 57 d.

aldoxycarbAcaricide, insecticide, nematicide

IRAC 1A

NOMENCLATURE:Common name aldoxycarb (BSI, E-ISO, ANSI, ESA); aldoxycarbe ((m) F-ISO)IUPAC name 2-mesyl-2-methylpropionaldehyde O-methylcarbamoyloxime; 2-methyl-2-methylsulfonylpropionaldehyde O-methylcarbamoyloximeChemical Abstracts name 2-methyl-2-(methylsulfonyl)propanal O-[(methylamino)carbonyl]oxime Other names aldicarb sulfone; sulfocarb CAS RN [1646884] Development codes UC 21 865 Smiles code CNC(=O)ON=CC(C)(C)S(=O)(=O)CPHYSICAL CHEMISTRY: Mol. wt. 222.3 M.f. C7H14N2O4S Form White crystalline powder with a sulfurous odour. M.p. 140142 C V.p. 12 mPa (25 C) Henry 2.67 104 Pa m3 mol1 (calc.) Solubility In water c. 10 g/l (25 C). In chloroform 32, acetonitrile 74, methanol 30, dichloromethane 41, acetone 50 (all in g/l). Stability Stable, but decomposition occurs above 140 C. Rapidly hydrolysed in acidic or alkaline media.COMMERCIALISATION:History Insecticide and nematicide reported by M. H. J. Weiden et al. (J. Econ. Entomol., 1965, 58, 154). Introduced by Union Carbide Corp. (later Rhne-Poulenc Agrochimie). Patents US 3217037 Manufacturers Rhne-PoulencAPPLICATIONS:Biochemistry Cholinesterase inhibitor. Mode of action Systemic; taken up through roots. Uses Control of aphids, thrips, mites, nematodes, leafhoppers and other pests on cotton, tobacco, peanuts, maize, potatoes, cole crops and vegetables. Could be applied as a soil treatment, foliar spray, seed dressing or transplant water treatment. Phytotoxicity Soya beans and french bean seedlings are not tolerant. Formulation types WP; GR; SC; FS. Compatibility Not fully known, but has been found to be compatible with most common herbicides, insecticides, nematicides and fungicides used on tobacco.PRODUCTS:Discontinued products Standak* (Rhne-Poulenc).

CHCCH3

CH3

N O CNHCH3

OCH3SO2

8


aldrin

ANALYSIS:Product analysis by i.r. spectrometry (CIPAC Handbook, 1980, 1A, 1094). Residues determined by glc with FPD (R. T. Krause, J. Assoc. Offic. Anal. Chem., 1980, 63, 1114; R. R. Romine, Anal. Methods Pestic. Plant Growth Regul., 1973, 7, 147; J. H. Smelt et al., loc. cit.). In drinking water by rplc and fluorimetry of liberated methylamine (Environ. Chem. Methods).TOXICOLOGICAL & ENVIRONMENTAL REVIEWS:EHC 64 (1986); a review of carbamate pesticides in general.MAMMALIAN TOXICOLOGY:Oral Acute oral LD50 for male rats 21.4 mg/kg. Skin and eye Acute percutaneous LD50 for rats 1000, rabbits 200 mg/kg. No skin or eye irritation in standard tests. Inhalation LC50 (4 h) for rats 0.14 mg/l air (dust). NOEL In life-span feeding trials, NOEL for mice 9.6, rats 2.4 mg/kg. ADI/RfD (EPA) 0.001 mg/kg b.w. [1993]. Other No teratogenic, reproductive or mutagenic effects observed. Toxicity Class WHO (a.i.) Ib EPA (formulation) IECOTOXICOLOGY:Birds Acute oral LD50 for mallard ducks 33.5 mg/kg. Dietary LC50 (5 d) for mallard ducks >10 000 mg/kg diet, bobwhite quail 5706 mg/kg diet. Fish LC50 (96 h) for trout 40, bluegill sunfish 55.5 mg/l. Bees Low toxicity to bees.ENVIRONMENTAL FATE:Animals Degradation in animals is by hydrolysis of the carbamate ester to aldoxycarb oxime, and elimination of the methylcarbamate group to give aldoxycarb nitrile. Plants Degradation in plants is the same as in animals. Soil/Environment See aldicarb. Details PM10, Entry 18.

aldrinInsecticide

IRAC 2A

NOMENCLATURE:Common name HHDN (for pure material) (BSI, E-ISO, F-ISO, JMAF; exception USA); aldrin (for material containing 95% HHDN) (BSI, E-ISO, ESA, JMAF); aldrine (for material containing 95% HHDN) ((m) F-ISO)IUPAC name (1R,4S,4aS,5S,8R,8aR)-1,2,3,4,10,10-hexachloro-1,4,4a,5,8,8a-hexahydro-1,4:5,8-dimethanonaphthalene; 1,2,3,4,10,10-hexachloro-1,4,4a,5,8,8a-hexahydro-exo-1,4-endo-5,8-dimethanonaphthaleneChemical Abstracts name (1,4,4a,5,8,8a)-1,2,3,4,10,10-hexachloro-1,4,4a,5,8,8a-hexahydro-1,4:5,8-dimethanonaphthalene CAS RN [309002]

Cl ClCl

ClCl

Cl


aldrin 9

EC no 2062158 Development codes Compound 118 (Hyman) Smiles code ClC1=C(Cl)C2(Cl)C3C4CC(C=C4)C3C1(Cl)C2(Cl)ClPHYSICAL CHEMISTRY: Mol. wt. 364.9 M.f. C12H8Cl6 Form Pure HHDN is a colourless crystalline solid; aldrin is a tan to dark brown waxy solid. M.p. 104104.5 C (HHDN); (aldrin 4960 C) B.p. 145 C /2 mmHg V.p. 8.6 mPa (20 C) Solubility In water 0.027 mg/l (27 C). In acetone, benzene and xylene >600 g/l (27 C). Stability Thermally stable up to 200 C. Stable between pH 4 and 8. Reacts with concentrated acids and phenols in the presence of oxidising agents to give dieldrin.COMMERCIALISATION:History Insecticide reported by C. W. Kearns et al. (J. Econ. Entomol., 1949, 42, 27). Introduced by J. Hyman & Co. and by Shell International Chemical Co., Ltd. Patents US 2635977 (to Hyman)APPLICATIONS:Biochemistry Antagonist of the GABA receptor-chloride channel complex. Mode of action Non-systemic insecticide with contact, stomach, and respiratory action. Uses Control of soil-dwelling insects including termites and ants at 0.55.0 kg/ha. Also used for wood preservation. Formulation types DP; EC; WP; GR.PRODUCTS:Discontinued products Aldrex* (Shell); Octalene* (Sandoz).ANALYSIS:TC and formulation analysis by i.r. spectrometry (CIPAC Handbook, 1983, 1B, 1706; AOAC Methods, 18th Ed., 961.05), by tlc (ibid., 972.05), by potentiometric titration of liberated chloride ion (CIPAC Handbook, 1994, F, 190), or by glc. Residues determined by glc, tlc or paper chromatography (AOAC Methods, 18th Ed., 970.52), or by glc with ECD (Anal. Methods Pestic. Plant Growth Regul., 1972, 6, 268; Analyst (London), 1979, 104, 425; P.A.Greve & W. B. F. Grevenstuk, Meded. Fac. Landbouwwet. Rijksuniv. Gent, 1975, 40, 1115; G. M. Telling, J. Chromatogr., 1977, 137, 405; M. A. Luke et al., J. Assoc. Off. Anal. Chem., 1981, 64, 1187). See also Pestic. Anal. Man., I, 208, 303, 503. In drinking water by glc with ECD (AOAC Methods, 18th Ed., 990.06).TOXICOLOGICAL & ENVIRONMENTAL REVIEWS:EHC 91 (1989). JMPR Mtg. 65 (1992); JMPR Evaln. I 66 (1992); JMPR Evaln. 29 (1977). HSG 21 (1989). PDS 41 (1979). ICSC.774 (1998). IARC 5 (1974); Suppl. 7 (1987). EU Status (1107/2009) Considered to be outside the scope of the Directive; already banned, 79/117/EC, as amended by Regulation 850/2004.MAMMALIAN TOXICOLOGY:IARC Class 3Oral Acute oral LD50 for rats 3867, guinea pigs 33, rabbits 5080, dogs 6595 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits 1525, rats 98 mg/kg. Toxic by skin absorption. NOEL LOAEL 0.025 mg/kg b.w. (EPA IRIS) ADI/RfD (JMPR) 0.0001 mg/kg b.w. (PTDI) [1994] (aldrin + dieldrin); (EPA) cRfD 0.00003 mg/kg b.w. [1988]. Water GV 0.03 ;g/l (sum of aldrin+dieldrin). Other Because aldrin is rapidly epoxidised

10


allidochlor

in living tissue, forming dieldrin (q.v.), the long term toxicology of dieldrin to laboratory animals can be regarded as representative of aldrin. Toxicity Class WHO (a.i.) Ib EPA (formulation) I ECClassification T; R24/25, R48/24/25| R40| N; R50, R53 PIC Yes.ECOTOXICOLOGY:Birds Acute oral LD50 for bobwhite quail 6.59, mallard 52 mg/kg. Fish LC50 (24 h) 0.0180.089 mg/l. Bees Toxic to bees.ENVIRONMENTAL FATE:Animals In living organisms, aldrin is rapidly epoxidised to dieldrin (q.v.). Soil/Environment In soil and water, undergoes epoxidation to dieldrin (q.v.). Details PM8, Entry 00120.

allidochlorHerbicide

NOMENCLATURE:Common name allidochlor (BSI, E-ISO); alidochlore ((m) F-ISO); CDAA (WSSA, JMAF)IUPAC name N,N-diallyl-2-chloroacetamideChemical Abstracts name 2-chloro-N,N-di-2-propenylacetamide CAS RN [93710] EC no 2022707 Development codes CP 6343 (Monsanto) Smiles code ClCC(=O)N(CC=C)CC=CPHYSICAL CHEMISTRY: Mol. wt. 173.6 M.f. C8H12ClNO Form Amber-coloured oil. B.p. 74 C /0.3 mmHg V.p. 1250 mPa (20 C) Kow logP = 0.97 (Agchem. Desk Ref.) S.g./density 1.088 (25 C) Solubility In water 20 g/kg (25 C). In chlorobenzene, chloroform, cyclohexanone, ethanol, and xylene >500 g/kg (25 C); in hexane >200 g/kg (36 C). Stability Stable to uv light; decomposes at 125 C.COMMERCIALISATION:History Herbicide reported by P. C. Hamm & A. J. Speziale (J. Agric. Food Chem., 1956, 4, 518). Introduced by Monsanto Co. Patents US 2864683APPLICATIONS:Biochemistry Inhibition of cell respiration. Mode of action Selective herbicide Uses A selective pre-em. herbicide used to control annual grasses and certain broad-leaved weeds in beans (various types), cabbages, celery, certain fruits, maize, onions, certain ornamentals, sugar cane and sweet potatoes. Incorporated into soil after pre-em. application; also used post-em. and absorbed by cotyledons of grass seedlings. Formulation types EC; GR.PRODUCTS:Discontinued products Randox* (Monsanto); Discontinued mixtures Randox-T* (+ trichlorobenzyl chloride) (Monsanto).ANALYSIS:Product and residue analysis is by glc.


allyl alcohol 11

MAMMALIAN TOXICOLOGY:Oral Acute oral LD50 for rats 700 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits 830 mg tech./kg. Corrosive to skin and eyes (rabbits). NOEL In 90 d feeding trials, no adverse effect observed in rats and dogs at 200 mg/kg diet (highest rate tested). Toxicity Class WHO (a.i.) IIECClassification Xn; R21/22| Xi; R36/38| N; R51, R53ECOTOXICOLOGY:Fish LC50 for rainbow trout 2.0 mg/l. Bees Not toxic to bees when used as prescribed.ENVIRONMENTAL FATE:Plants In plants, it is readily metabolised to glycollic acid and diallylamine. Soil/Environment Rapid hydrolytic cleavage of chlorine atom with formation of water-soluble metabolites. There is oxidative attack on the allyl group. Glycolic acid is also a metabolite. Loss from soil is mainly by microbial activity, but soil incorporation is needed because of its volatility. Duration of activity 36 weeks, depending on soil. Details PM7, Entry 00140.

allyl alcoholHerbicide

NOMENCLATURE:Common name allyl alcohol (BSI, ISO, accepted in lieu of common name)IUPAC name allyl alcohol; prop-2-en-1-olChemical Abstracts name 2-propen-1-ol CAS RN [107186] EC no 2034707PHYSICAL CHEMISTRY: Mol. wt. 58.08 M.f. C3H6O Form Colourless, mobile liquid with a pungent odour. M.p. forms a glass at 190 C B.p. 96.9 C V.p. 2.31 106 mPa (20 C) S.g./density 0.8535 at 20 C Solubility Miscible with water and common organic solvents. Stability Polymerises on storage and therefore requires the addition of a stabiliser. Stable in uv light. F.p. 32 C (open cup)COMMERCIALISATION:History Its experimental use as a herbicide first reported in 1950.APPLICATIONS:Mode of action Inhibits germination. Uses Herbicide for control of weed and grass seeds. Applied to nursery, forestry, vegetable, tobacco, and other seeds beds, at 85170 g in 50 000100 000 l water/ha. Also for the partial sterilisation of glasshouse soil (E. M. Emmert & J. E. Klinker, Ky. Agric. Exp. Stn. Prog. Rep., 1950) at 18.4 g in 6.1 l water/m2 of soil. Formulation types TC.ANALYSIS:

CH2CH

H2COH

12


allyxycarb

Product analysis by measurement of the bromine added across the double-bond or acetylation of the hydroxyl group in the presence of pyridine. For a polarographic determination see M. Jaworski and J. Bogaczek (Chem. Anal. (Warsaw) 1969, 14, 12471251), reported in Fresenius Z. Anal. Chem. 1971, 257, 70. It may be detected by trapping in water or sulfuric acid and oxidising to acrylaldehyde by chromic-sulfuric acid. For detection of residues in soil before sowing, the biological cress root test is mostly applied.TOXICOLOGICAL & ENVIRONMENTAL REVIEWS:ICSC 0095 (2000). EU Status (1107/2009) Not approved, Commission Regulation 2076/2002.MAMMALIAN TOXICOLOGY:Oral Acute oral LD50 for rats 64, mice 85 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits 89 mg/kg; absorbed rapidly through the skin. Lachrymatory and intensely irritating to skin and mucous membranes. Inhalation High inhalation toxicity. NOEL Highest oral dose without activity for male and female rats 4.8 and 6.2 mg/kg daily (15 w). ADI/RfD (EPA) cRfD 0.005 mg/kg b.w. [1989]. Other Maximum acceptable concentration in work-place atmosphere over an 8-hour work period 5 mg/m3. Toxicity Class WHO (a.i.) IbECClassification R10| T; R23/24/25| Xi; R36/37/38| N; R50ECOTOXICOLOGY:Fish Toxic to fish. Bees Not toxic to bees when used as prescribed.ENVIRONMENTAL FATE:Soil/Environment Metabolism not known. It disappears for the most part through evaporation. Duration of activity 310 days depending on temperature, soil type, and humidity. Details PM6, p. 9.

allyxycarbInsecticide

NOMENCLATURE:Common name allyxycarb (BSI, E-ISO); allyxycarbe (F-ISO); APC (JMAF)IUPAC name 4-diallylamino-3,5-xylyl methylcarbamateChemical Abstracts name 4-(di-2-propenylamino)-3,5-dimethylphenyl methylcarbamate CAS RN [6392467] Development codes Bayer 50 282; A 546 Smiles code CNC(=O)Oc1cc(C)c(N(CC=C)CC=C)c(C)c1PHYSICAL CHEMISTRY: Mol. wt. 274.4 M.f. C16H22N2O2COMMERCIALISATION:History Insecticide introduced by Bayer AG.APPLICATIONS:Biochemistry Cholinesterase inhibitor.


amibuzin 13

TOXICOLOGICAL & ENVIRONMENTAL REVIEWS:EHC 64 (1986; a review of carbamate pesticides in general).MAMMALIAN TOXICOLOGY:Toxicity Class WHO (a.i.) O Details PM4, p. 10.

aloracPlant growth regulator

NOMENCLATURE:Common name alorac (BSI, E-ISO, (m) F-ISO)IUPAC name (Z)-perchloro-4-oxopent-2-enoic acid; (Z)-2,3,5,5,5-pentachloro-4-oxopent-2-enoic acidChemical Abstracts name (Z)-2,3,5,5,5-pentachloro-4-oxo-2-pentenoic acid CAS RN [19360022] Smiles code OC(=O)/C(=C(/Cl)\C(=O)C(Cl)(Cl)Cl)/Cl;without stereochemistry:OC(=O)C(=C(Cl)C(=O)C(Cl)(Cl)Cl)ClPHYSICAL CHEMISTRY: Mol. wt. 286.3 M.f. C5HCl5O3COMMERCIALISATION:History Plant growth regulator.

ametridioneHerbicide

NOMENCLATURE:Common name am(tridione) ((m) F-ISO); ametridione (BSI, E-ISO)IUPAC name 1-amino-6-ethylthio-3-neopentyl-1,3,5-triazine-2,4(1H,3H)-dioneChemical Abstracts name 1-amino-3-(2,2-dimethylpropyl)-6-(ethylthio)-1,3,5-triazine-2,4(1H,3H)-dione CAS RN [78168931] Development codes BAY SSH 0860 Smiles code CCSc1nc(=O)n(CC(C)(C)C)c(=O)n1NPHYSICAL CHEMISTRY: Mol. wt. 258.3 M.f. C10H18N4O2SCOMMERCIALISATION:History Herbicide evaluated by Bayer AG.

amibuzinHerbicide

NOMENCLATURE:Common name amibuzine ((f) F-ISO); amibuzin (BSI, E-ISO)IUPAC name 6-tert-butyl-3-dimethylamino-4-methyl-1,2,4-triazin-5(4H)-one

14


amidochlor

Chemical Abstracts name 3-(dimethylamino)-6-(1,1-dimethylethyl)-4-methyl-1,2,4-triazin-5(4H)-one CAS RN [76636107] Development codes DIC 3202 Smiles code CN(C)c1nnc(c(=O)n1C)C(C)(C)CPHYSICAL CHEMISTRY: Mol. wt. 210.3 M.f. C10H18N4OCOMMERCIALISATION:History Herbicide developed by Bayer AG.

amidithionAcaricide, insecticide

IRAC 1BNOMENCLATURE:Common name amidiphos ((m) France); amidithion (BSI, E-ISO, (m) F-ISO, ESA, ex-ANSI)IUPAC name S-2-methoxyethylcarbamoylmethyl O,O-dimethyl phosphorodithioate; 2-dimethoxyphosphinothioylthio-N-(2-methoxyethyl)acetamideChemical Abstracts name S-[2-[(2-methoxyethyl)amino]-2-oxoethyl] O,O-dimethyl phosphorodithioate CAS RN [919766] Development codes Ciba 2446 Smiles code COCCNC(=O)CSP(=S)(OC)OCPHYSICAL CHEMISTRY: Mol. wt. 273.3 M.f. C7H16NO4PS2COMMERCIALISATION:History Acaricide and insecticide (V. Dittrich & F. Bachman, Proc. Br. Insectic. Fungic. Conf., 2nd, 1963, p. 421). Introduced by Ciba AG (later Ciba-Geigy AG).APPLICATIONS:Biochemistry Cholinesterase inhibitor.TOXICOLOGICAL & ENVIRONMENTAL REVIEWS:EHC 63 (1986; a general review of organophosphorus insecticides).MAMMALIAN TOXICOLOGY:Toxicity Class WHO (a.i.) OECClassification Xn; R22 Details PM2, p. 16.

amidochlorPlant growth regulator

NOMENCLATURE:Common name amidochlor (ANSI)IUPAC name N-acetamidomethyl-2-chloro-2,6-diethylacetanilideChemical Abstracts name N-[(acetylamino)methyl]-2-chloro-N-(2,6-diethylphenyl)acetamide CAS RN [40164678] Development codes MON 4620; CP-76 963


aminocarb 15

Smiles code CCc1cccc(CC)c1N(CNC(=O)C)C(=O)CClPHYSICAL CHEMISTRY: Mol. wt. 296.8 M.f. C15H21ClN2O2COMMERCIALISATION:History Plant growth regulator introduced by Monsanto Co.PRODUCTS:Discontinued products Limit* (Monsanto).

amidothioateAcaricide, insecticide

IRAC 1BNOMENCLATURE:Common name amidothioate (JMAF)IUPAC name O-2-chloro-4-methylthiophenyl O-methyl ethylphosphoramidothioateChemical Abstracts name O-[2-chloro-4-(methylthio)phenyl] O-methyl ethylphosphoramidothioate CAS RN [54381269] Development codes NK-11 Smiles code CCNP(=S)(OC)Oc1ccc(SC)cc1ClPHYSICAL CHEMISTRY: Mol. wt. 311.8 M.f. C10H15ClNO2PS2COMMERCIALISATION:History Acaricide introduced by Nippon Kayaku Co., Ltd.APPLICATIONS:Biochemistry Cholinesterase inhibitor.

aminocarbInsecticide

IRAC 1ANOMENCLATURE:Common name aminocarb (BSI, E-ISO, ESA); aminocarbe ((m) F-ISO)IUPAC name 4-dimethylamino-m-tolyl methylcarbamateChemical Abstracts name 4-(dimethylamino)-3-methylphenyl methylcarbamate Other names DTMC CAS RN [2032599] EC no 2179907 Development codes Bayer 44 646; A 363 Smiles code CNC(=O)Oc1ccc(N(C)C)c(C)c1PHYSICAL CHEMISTRY: Mol. wt. 208.3 M.f. C11H16N2O2 Form Colourless crystalline solid. M.p. 9394 C V.p. 2.3 mPa (EPA, 1988) Solubility In water 915 mg/kg (20 C) (Agchem. Desk Ref.). Moderately soluble in aromatic solvents; soluble in polar organic solvents.COMMERCIALISATION:

16


amiprofos-methyl

History Insecticide reported by G. Unterstenhfer (Meded. Landbouwhogesch. Opzoekingsstn. Staat Gent, 1963, 28, 758). Introduced by Bayer AG. Patents DE 1145162APPLICATIONS:Biochemistry Cholinesterase inhibitor. Mode of action Non-systemic insecticide with contact and stomach action. Uses Mainly used against lepidopterous larvae and other chewing insects; generally recommended at 75 g/100 l. Formulation types WP. Compatibility Incompatible with highly alkaline pesticides.PRODUCTS:Discontinued products Matacil* (Bayer); Metacil* (Bayer).ANALYSIS:Product analysis by rplc (CIPAC Handbook, 1988, D, 7) or lc (AOAC Methods, 18th Ed., 985.02; J. Assoc. Off. Anal. Chem., 1985, 68, 372, 6.A256.A30) or by uv spectroscopy (H. Niessen & H. Frehse, Pflanz.-Nachr. Bayer (Engl. Ed.), 1963, 16, 205). Residues determined by uv spectroscopy or by glc of a derivative (R. J. Argauer, J. Agric. Food Chem., 1969, 17, 888; E. R. Holden et al., ibid., p.56; L. I. Butler & L. M. McDonough, ibid., 1968, 16, 403). See also Pestic. Anal. Man., I, 302.TOXICOLOGICAL & ENVIRONMENTAL REVIEWS:EHC 64 (1986; a review of carbamate pesticides in general). JMPR Evaln. 33 (1979). ICSC 0097 (1994).MAMMALIAN TOXICOLOGY:Oral Acute oral LD50 for rats 3050 mg/kg. Skin and eye Acute percutaneous LD50 for rats 275 mg/kg. NOEL In 2 y feeding trials, rats receiving 200 mg/kg diet showed no symptom of poisoning. ADI/RfD (JMPR) No ADI [1979]. Other Acute i.p. LD50 for rats 21 mg/kg. Toxicity Class WHO (a.i.) IbECClassification T; R24/25| N; R50, R53ECOTOXICOLOGY:Bees Toxic to bees. Details PM8, Entry 00270.

amiprofos-methylHerbicide

HRAC K1 WSSA 3; phosphoroamidateNOMENCLATURE:Common name amiprofos-methyl (BSI, E-ISO, (m) F-ISO)IUPAC name O-methyl O-2-nitro-p-tolyl isopropylphosphoramidothioateChemical Abstracts name O-methyl O-(4-methyl-2-nitrophenyl) (1-methylethyl)phosphoramidothioate Other names amiprophos-methyl CAS RN [36001884] Development codes BAY NTN 6867; NTN 2925 Smiles code COP(=S)(NC(C)C)Oc1ccc(C)cc1[N+](=O)[O-]PHYSICAL CHEMISTRY: Mol. wt. 304.3 M.f. C11H17N2O4PS


ampropylfos 17

COMMERCIALISATION:History Herbicide reported by M. Aya et al. (Zasso Kenkyu, 1973, (15), p. 20). Evaluated by Bayer AG.APPLICATIONS:Biochemistry Microtubule assembly inhibition.

amiton; amiton hydrogen oxalateAcaricide, insecticide

IRAC 1BNOMENCLATURE:Common name amiton (BSI)IUPAC name S-2-diethylaminoethyl O,O-diethyl phosphorothioateChemical Abstracts name S-[2-(diethylamino)ethyl] O,O-diethyl phosphorothioate CAS RN [78535] amiton; [3734972] amiton hydrogen oxalate Development codes R 5158 (amiton); R 6199 (amiton hydrogen oxalate)PHYSICAL CHEMISTRY: Mol. wt. 269.3; (oxalate 359.4) M.f. C10H24NO3PS; (oxalate C12H26NO7PS)COMMERCIALISATION:History Insecticide and acaricide reported by R. Ghosh & J. F. Newman (Chem. Ind. (London), 1955, p. 118) and by G. L. Baldit (J. Sci. Food Agric., 1958, 9, 516). Evaluated by Plant Protection Ltd (later ICI Agrochemicals).APPLICATIONS:Biochemistry Cholinesterase inhibitor.PRODUCTS:Discontinued products Tetram* (oxalate) (ICI).TOXICOLOGICAL & ENVIRONMENTAL REVIEWS:EHC 63 (1986; a general review of organophosphorus insecticides).

ampropylfosFungicide

NOMENCLATURE:Common name ampropylfos (BSI, E-ISO, (m) F-ISO)IUPAC name (RS)-1-aminopropylphosphonic acid

HO POH

CHCH2CH3O NH2

18


ampropylfos

Chemical Abstracts name ()-(1-aminopropyl)phosphonic acid CAS RN [16606647] Development codes PNL-62 Smiles code CCC(N)P(=O)(O)OPHYSICAL CHEMISTRY: Mol. wt. 139.1 M.f. C3H10NO3P Form White solid. M.p. 264270 C V.p. 3.7 103 mPa (90 C) Kow logP = 3 S.g./density 0.5 Solubility In water 139 g/l (21 C). In methanol 0.46, isopropanol 0.003, hexane, toluene, dichloromethane, ethyl acetate, and acetone 0.0001 (all in g/l, 21 C). Stability Stable 2 y (pH 47, 20 C); stable >31 d (pH 9, 25 C); stable 3 d (pH 4, 100 C). pKa pKa2 5.9, pKa3 10.4COMMERCIALISATION:History Fungicide discovered by KenoGard AB (later Rhne-Poulenc Agrochimie).Manufacturers Rhne-PoulencAPPLICATIONS: Uses Control of covered smut, loose smut, Fusarium spp., leaf stripe, and net blotch in barley, and leaf stripe and loose smut in oats. Formulation types SC.PRODUCTS:Discontinued mixtures Ravyl* (+ anthraquinone + myclobutanil) (Bayer).ANALYSIS:Product by hplc with uv detection at 220 nm.TOXICOLOGICAL & ENVIRONMENTAL REVIEWS:EU Status (1107/2009) Not approved, Commission Regulation 2076/2002.MAMMALIAN TOXICOLOGY:Oral Acute oral LD50 for rats >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Non-sensitising to skin (guinea pigs). Non-irritating to skin of rabbits. Inhalation LC50 for rats >4 mg/l air. NOEL (90 d) for rats 100 mg/kg daily (only minimal changes at 300 mg/kg daily). In 90 d feeding trials, 0.1% PNL 62 in the diet had no effect on dogs after 13 w treatment (effects at 0.5% were minimal and there is no evidence of systemic or target organ toxicity). Non-teratogenic to rats at 1000 mg/kg daily. Non-teratogenic to rabbits at 10 mg/kg daily. Other Intravenous LD50 for rats c. 1250 mg/kg. Non-mutagenic in the Ames test and other mutagenicity tests.ECOTOXICOLOGY:Birds Acute oral LD50 for bobwhite quail and mallard ducks >2000 mg/kg. Dietary LC50 for bobwhite quail and mallard ducks >5000 mg/kg. No observed neurotoxicity to hens. Fish LC50 (96 h) for rainbow trout, bluegill sunfish, and mirror carp >135 mg/l. Daphnia LC50 (24 and 48 h) >100 mg/l. Algae EC50 for Selenastrum capricornutum 54 mg/l. Worms LC50 for Eisenia foetida >1000 mg/kg.ENVIRONMENTAL FATE:Animals After oral administration to rats of a single dose of 200 mg ampropylfos/kg b.w. there is a rapid absorption (about 50%) with peak concentration 1 h after dosage, and a fast decline in a bioexponential manner with DT50 c. 2 h in plasma, 50 h in blood. Similar


anabasine 19

decline is found after intravenous administration in rats. Whole body autoradiograms of rats showed that 14C-labelled ampropylfos is widely distributed in tissues as well as being taken up to some extent into bone and blood cells. There is no evidence of 14C-labelled ampropylfos-related material crossing either the placental or blood brain barriers. Plants Uptake of 14C-labelled ampropylfos (applied as a seed dressing formulation at a level of 400 mg/kg seed) from seeds of winter barley is very low. Soil/Environment Ampropylfos is strongly bound to soil. The percentage of applied 14C-labelled ampropylfos eluted from three standard soil types was 0.61 (sand), 0.035 (loamy sand), 0.925 (sandy loam) (14C-labelled ampropylfos applied in an amount corresponding to a field application rate of 1500 g/ha and water added equivalent to 200 mm rain). Ampropylfos is readily biodegradable in freshwater to levels of 81% and 79% within 35 days at 22.5 2.5 C using unacclimatised and acclimatised inocula, respectively. No photodegradation of ampropylfos was observed in artificial sunlight after 34 days of continuous irradiation in pH 5, pH 7, and pH 9 buffered aqueous solutions at 25 C (1 day of artificial sunlight was equivalent to 1.25 days of natural sunlight). Details PM9, Entry 0375.

anabasineInsecticide

NOMENCLATURE:Common name anabasine (JMAF)IUPAC name (S)-3-(piperidin-2-yl)pyridineChemical Abstracts name (S)-3-(2-piperidinyl)pyridine Other names 2-(3-pyridyl)piperidine CAS RN [494520]; [13078041] racemate Smiles code C1CCC(NC1)c2cccnc2PHYSICAL CHEMISTRY: Mol. wt. 162.2 M.f. C10H14N2 M.p. Freezes 9 C B.p. 281 C S.g./density 1.048 (20 C) Solubility Miscible with water and most organic solvents.COMMERCIALISATION:Production Obtained, as racemic material, from Nicotiana glauca. History Insecticide isolated in 1931 from Anabasis aphylla.APPLICATIONS:Biochemistry Agonist of nicotine acetylcholine receptors.

20


anilazine

anilazineFungicide

FRAC M8, M; multi-site: triazine fungicideNOMENCLATURE:Common name anilazine (BSI, E-ISO, (f) F-ISO); triazine (JMAF)IUPAC name 4,6-dichloro-N-(2-chlorophenyl)-1,3,5-triazin-2-amine; 2-chloro-N-(4,6-dichloro-1,3,5-triazin-2-yl)anilineChemical Abstracts name 4,6-dichloro-N-(2-chlorophenyl)-1,3,5-triazin-2-amine CAS RN [101053] EC no 2029105 Development codes B-622 (Ethyl Corp.) Smiles code Clc1ccccc1Nc2nc(Cl)nc(Cl)n2PHYSICAL CHEMISTRY: Mol. wt. 275.5 M.f. C9H5Cl3N4 Form Colourless to tan crystals. M.p. 159 C V.p. 8.2 104 mPa (20 C) Kow logP = 3.02 (20 C) Henry 2.82 105 Pa m3 mol1 (calc.) S.g./density 1.8 (20 C) Solubility In water 8 mg/l (20 C). In acetone 100, chlorobenzene 60, toluene 50, xylene 40 (all in g/l, 30 C). In dichloromethane 90, isopropanol 8, hexane 1.7 (all in g/l, 20 C). Stability Stable in neutral and slightly acidic media. Hydrolysed on heating with alkalis; DT50 (22 C) 730 h (pH 4), 790 h (pH 7), 22 h (pH 9).COMMERCIALISATION:History Fungicide reported by C. N. Wolf et al. (Science, 1955, 121, 61). Introduced by the Ethyl Corp. and later by Nippon Soda Co., Ltd and by Bayer AG. Patents US 2720480 (to Ethyl Corp.) Manufacturers Bayer CropScienceAPPLICATIONS:Biochemistry Multi-site action. Mode of action Non-systemic foliar fungicide, with protective action. Uses Control of Septoria spp. of wheat (glume blotch and on leaves) was the main area of use. Also used for the control of early and late blights of potatoes and tomatoes; anthracnose in cucurbits; leaf spot diseases (Alternaria, Cercospora, and Septoria spp.) in many crops; Helminthosporium spp. in wheat and barley; brown patch, dollar spot, snow mould, and other diseases of turf; Botrytis, Colletotrichum, Leptosphaeria, and Pyrenophora spp. on many crops; etc. Also used on vegetables, ornamentals, berry fruit, melons, water melons, coffee, and tobacco. Formulation types WP; SC. Compatibility Incompatible with oils and alkaline materials.PRODUCTS:Discontinued products Dyrene* (Bayer); Kemate* (Bayer); Triazine* (Nippon Soda); Triazin Jet* (Nippon Soda).

N N

N NH

Cl

ClCl


anisuron 21

ANALYSIS:Product analysis by lc (AOAC Methods, 18th Ed., 988.04; CIPAC Handbook, 1992, E, 5) or by hydrolysis and measurement of the chloride liberated (P. F. Kane & K. G. Gillespie, J. Agric. Food Chem., 1960, 8, 29). Methods for determination of residues were available from Bayer.TOXICOLOGICAL & ENVIRONMENTAL REVIEWS:JMPR Mtg. 65 (1992); JMPR Evaln. I 66 (1992); JMPR Evaln. II 58 (1989). EU Status (1107/2009) Not approved, Commission Regulation 2076/2002.MAMMALIAN TOXICOLOGY:Oral Acute oral LD50 for rats >4000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >5000 mg/kg. Severe eye irritant; mild skin irritant (rabbits). Inhalation LC50 for rats (4 h) >0.25 mg/l air (aerosol), (1 h) >0.7 mg/l air (dust). NOEL (2 y) for rats 2000, mice 1250 mg/kg diet; (18 mo) for dogs 40 mg/kg b.w. ADI/RfD (JMPR) 0.1 mg/kg b.w. [1989]; (EPA) 0.0004 mg/kg b.w. [1989]. Toxicity Class WHO (a.i.) U; (WHO Recommended Classification gives O) EPA (formulation) II ECClassification Xi; R36/38| N; R50, R53ECOTOXICOLOGY:Birds Acute oral LD50 for Virginia quail >2000 mg/kg b.w. LC50 (5 d) for mallard ducks >5000 mg/kg. Fish LC50 (96 h) for rainbow trout and golden orfe 0.15 mg/l. Daphnia LC50 (48 h) 0.07 mg/l. Bees Not harmful to bees at recommended application rates.ENVIRONMENTAL FATE:Animals Elimination is quick; almost 98% is excreted within 72 h in the urine and faeces. Plants In plants, one or both chlorine atoms in the triazine ring are substituted by amino or thio groups, through reaction with amino acids, peptides, coenzymes, and other endogenous substances in the cellular system of the plant (R. G. Owens Ann. New York Acad. Sci. 1969, 160, 114132). Soil/Environment DT50 in damp soilc. 12 h. Readily degraded in different soils. Details PM10, Entry 29.

anisuronHerbicide

NOMENCLATURE:Common name anisuron (BSI) IUPAC name 1-(3,4-dichlorophenyl)-1-(4-methoxybenzoyl)-3,3-dimethylurea Chemical Abstracts name N-(3,4-dichlorophenyl)-N-[(dimethylamino)carbonyl]-4-methoxybenzamide CAS RN [2689432] Smiles code COc1ccc(cc1)C(=O)N(C(=O)N(C)C)c2ccc(Cl)c(Cl)c2PHYSICAL CHEMISTRY: Mol. wt. 367.2 M.f. C17H16Cl2N2O3COMMERCIALISATION:History Herbicide.

22


antu

antuRodenticide

NOMENCLATURE:Common name antu (BSI, E-ISO, (m) F-ISO, JMAF)IUPAC name 1-(1-naphthyl)-2-thioureaChemical Abstracts name 1-naphthalenylthiourea Other names -naphthylthiourea CAS RN [86884] EC no 2017063 Smiles code NC(=S)Nc1cccc2ccccc12PHYSICAL CHEMISTRY: Mol. wt. 202.3 M.f. C11H10N2S Form Colourless crystals; (tech. is a blue-grey powder). M.p. 198 C Solubility In water 600 mg/l (room temperature). In acetone 24.3, triethyleneglycol 86 (both g/l, room temperature). Stability Stable on exposure to air and to sunlight.COMMERCIALISATION:History Toxicity to rodents reported by C. F. Richter (J. Am. Med. Assoc., 1945, 129, 927; Proc. Soc. Exp. Biol. Med., 1946, 63, 364). Patents US 2390848APPLICATIONS: Uses A rodenticide specific for adult Rattus norvegicus for which the toxic dose is 68 mg/kg. It is less toxic to other Rattus spp. and tolerance is developed in rats by repeated administration of sub-lethal doses. Formulation types RB; CP.ANALYSIS:Product analysis is by reaction with silver nitrate and titration of the liberated nitric acid. (CIPAC Handbook, 1970, 1, 16; AOAC Methods, 18th Ed., 948.03, see 10th Ed., 4.132). Residues determined by colorimetry of a derivative (E. Bremais & K. G. Bergner, Pharm. Zentralhalle, 1950, 89, 115).TOXICOLOGICAL & ENVIRONMENTAL REVIEWS:ICSC.973 (2000). IARC 30 (1983); suppl. 7 (1987).MAMMALIAN TOXICOLOGY:IARC Class 3Oral Acute oral LD50 for Norwegian rats 68 mg/kg; less toxic for other rat species; surviving rats develop tolerance. Acute oral LD50 for monkeys 4250, dogs 38 mg/kg. Relatively safe for domestic animals; induces vomiting in dogs. Pigs are very sensitive. Very low human toxicity. Other Naphthylamines, present as impurities, are carcinogenic. Toxicity Class WHO (a.i.) IbECClassification T+; R28| R40ECOTOXICOLOGY:Birds Chickens are very sensitive.ENVIRONMENTAL FATE:Animals In rats, following oral administration, 40% is eliminated within 20 h. Metabolised by lung and liver microsomal preparations into 1-naphthylurea and sulfur. Details PM8, Entry 00450.


arsenous oxide 23

aramiteAcaricide

NOMENCLATURE:Common name aramite (JMAF)IUPAC name 2-(4-tert-butylphenoxy)-1-methylethyl 2-chloroethyl sulfiteChemical Abstracts name 2-chloroethyl 2-[4-(1,1-dimethylethyl)phenoxy]-1-methylethyl sulfite CAS RN [140578] Development codes 88-R Smiles code CC(COc1ccc(cc1)C(C)(C)C)OS(=O)OCCClPHYSICAL CHEMISTRY: Mol. wt. 334.9 M.f. C15H23ClO4SCOMMERCIALISATION:History Acaricide reported by W. D. Harris & J. W. Zukel (J. Agric. Food Chem., 1954, 2, 140). Introduced by Uniroyal Chemical Co., Inc.PRODUCTS:Discontinued products Aramite* (Uniroyal); Niagaramite* (FMC).ANALYSIS:Residues determined colorimetrically (AOAC Methods, 18th Ed., 959.10, see 12th Ed., 29.06729.071).TOXICOLOGICAL & ENVIRONMENTAL REVIEWS:IARC 5 (1974). EU Status (1107/2009) Never notified to the EU.MAMMALIAN TOXICOLOGY:IARC Class 2B Toxicity Class WHO (a.i.) O Details PM3, p. 73.

arsenous oxideRodenticide

NOMENCLATURE:Common name arsenious acid (JMAF); arsenous oxide (E-ISO, accepted in lieu of a common name); oxyde arsenieux (F-ISO, accepted in lieu of a common name.)IUPAC name diarsenic trioxide; arsenic trioxideChemical Abstracts name arsenic oxide (As2O3) Other names arsenious oxide; white arsenic CAS RN [1327533] EC no 2154814 Smiles code o1[as]2o[as]3o[as]1o[as](o2)o3PHYSICAL CHEMISTRY: Mol. wt. 395.7 M.f. As4O6 Form Colourless solid which exists in rhombic, octahedral and amorphous forms. The amorphous form is unstable, reverting to the octahedral. M.p. 272 C, subliming 125150 C (octahedral); 312 C (rhombic) V.p. 8.8 kPa (312 C) (rhombic form) Solubility In water 17 g/l (16 C). Practically insoluble in chloroform, diethyl ether, ethanol. Stability Stable in air but oxidised slowly in acid media. Dissolves in alkali to form arsenites.

24


asomate

COMMERCIALISATION:History Used as a rodenticide since the 16th century.APPLICATIONS: Uses Used in baits to control Rattus norvegicus, R. rattus and Mus musculus. It has also been used as a sheep dip to control ectoparasites. Formulation types PA .ANALYSIS:Product analysis by titration with iodine (WHO Specifications Insectic. (2nd Ed.). Residues determined by atomic absorption spectroscopy (AOAC Methods, 14th Ed., 25.00125.007) by colorimetry (ibid., 25.04125.055) or by the Gutzeit method (ibid., 25.045; 12th Ed., 25.00625.009).TOXICOLOGICAL & ENVIRONMENTAL REVIEWS:EHC 224 (2001). HSG 70 (1992). ICSC.378 (1997). IARC 23 (1980), Suppl 7 (1987).MAMMALIAN TOXICOLOGY:IARC Class 1 (evaluation applies to arsenic compounds as a whole, not necessarily to all individual compounds within the group)Oral Acute oral LD50 for rats 180200 mg a.i. (in carbohydrate or protein)/kg, 300 mg (in bacon fat)/kg, 20 mg (in aqueous solution)/kg (E. Packman et al., J. Agric. Food Chem., 1961, 9, 271); for mice 34.463.5 mg/kg (J. W. E. Harrison, AMA Arch. Ind. Health, 1958, 17, 118). Other It is extremely toxic to man, the minimum lethal dose is 2 mg/kg (H. O. Calvery, J. Am. Med. Assoc., 1938, 111, 1722). It is non-cumulative and is eliminated from the animal body in 742 d. Evidence of carcinogenicity in humans. Toxicity Class WHO (a.i.) Ia (sodium arsenite Class Ib)ECClassification R45| T+; R28| C; R34| N; R50, R53 Details PM9, Entry 460.

asomateChemosterilant

NOMENCLATURE:IUPAC name arsinetriyl tris(dimethyldithiocarbamate); 1-{[bis(dimethylthiocarbamoylsulfanyl)arsanyl]sulfanyl}-N,N-dimethylmethanethioamide; tris(dimethylthiocarbamoylthio)arsine Chemical Abstracts name N,N-dimethylcarbamodithioic acid anhydrosulfide with arsenotrithious acid (3:1); tris(dimethyldithiocarbamato)arsenic

AsSS

S

N

S

CH3H3C

NMe

Me

S

NSH3C

CH3


atraton 25

Other names TDDA; TTCA CAS RN [3586605] Smiles code S=C(N(C)C)S[As](SC(N(C)C)=S)SC(N(C)C)=SPHYSICAL CHEMISTRY: Mol. wt. 435.6 M.f. C9H18AsN3S6 Form Yellow-green crystals.APPLICATIONS:Mode of action Preventative and curative fungicide. Uses Used on apples and pears, powdery mildew of cucumber, grapes etc. Also for rice blast. Formulation types WP.MAMMALIAN TOXICOLOGY:Oral Acute oral LD50 for rats 335-370 mg/kg. Skin and eye Strong skin irritant.

athidathionInsecticide

IRAC 1BNOMENCLATURE:Common name athidathion (BSI, E-ISO, (m) F-ISO)IUPAC name O,O-diethyl S-2,3-dihydro-5-methoxy-2-oxo-1,3,4-thiadiazol-3-ylmethyl phosphorodithioate; 2-diethoxyphosphinothioylthiomethyl-5-methoxy-1,3,4-thiadiazol-2(3H)-oneChemical Abstracts name O,O-diethyl S-[(5-methoxy-2-oxo-1,3,4-thiadiazol-3(2H)-yl)methyl] phosphorodithioate CAS RN [19691806] Development codes G 13 006 Smiles code CCOP(=S)(OCC)SCn1nc(OC)sc1=OPHYSICAL CHEMISTRY: Mol. wt. 330.4 M.f. C8H15N2O4PS3COMMERCIALISATION:History Insecticide reported by K. Rfenacht (Helv. Chim. Acta, 1968, 51, 518). Introduced by J. R. Geigy S.A. (later Ciba-Geigy AG).APPLICATIONS:Biochemistry Cholinesterase inhibitor.PRODUCTS:Discontinued products Deltacron* (Geigy).MAMMALIAN TOXICOLOGY:Toxicity Class WHO (a.i.) O

atratonHerbicide

NOMENCLATURE:Common name atraton (BSI, E-ISO, (f) F-ISO); atratone ((f) France, former name (BSI))IUPAC name N2-ethyl-N4-isopropyl-6-methoxy-1,3,5-triazine-2,4-diamine

26


azafenidin

Chemical Abstracts name N-ethyl-6-methoxy-N-(1-methylethyl)-1,3,5-triazine-2,4-diamine CAS RN [1610179] Development codes G 32 293 Smiles code CCNc1nc(NC(C)C)nc(OC)n1PHYSICAL CHEMISTRY: Mol. wt. 211.3 M.f. C9H17N5O M.p. 9496 C V.p. 3.8 mPa (20 C) Henry 4.46 104 Pa m3 mol1 (calc.) Solubility In water 0.18% (20 C). Soluble in ketones, esters, ether, alcohols and other organic solvents. Stability Stable in neutral, weakly acidic and weakly basic media. Hydrolysed by warm acids and alkalis.COMMERCIALISATION:History Herbicide reported by E. Knsli (Phytiatr.-Phytopharm., 1958, 7, 81). Introduced by J. R. Geigy S.A. (later Ciba-Geigy AG).APPLICATIONS:Biochemistry Interferes with photosynthesis and other enzymic processes. Uses Selective herbicide used to protect sugar cane. Was also a component in total herbicide mixtures. Formulation types WP; EC.ANALYSIS:Product by extraction with ether and titration of one amino group with perchloric acid (Anal. Methods Pestic. Plant Growth Regul., 4, 28, 173). Residues by extraction with methylene chloride, hydrolysis with 0.1 N sulphuric acid, and spectrophotometric determination of the hydroxy derivative at 240 nm (Anal. Methods Pestic. Plant Growth Regul. 4, 28). For determination by tlc, spectrophotometry, and gc, see Man. Pestic. Residue Anal., 6AC. For gc determination with prometon as internal standard, see Anal. Methods Pestic. Plant Growth Regul. 1972, 6, 597599. In drinking water by glc with NPD (AOAC Methods, 18th Ed., 991.07).MAMMALIAN TOXICOLOGY:Oral Acute oral LD50 for rats 14652400, mice 905 mg/kg. Skin and eye Feeding 50% atraton to rats at 10 and 200 mg/kg b.w. for 90 d produces no signs of illness. Toxicity Class WHO (a.i.) OENVIRONMENTAL FATE:Soil/Environment Replacement of the methoxy group at C-2 by hydrolysis via the hydroxyl group. Dealkylation of the amino substituents at C-4 and C-6. Possibly opening of the triazine ring.

azafenidinHerbicide

NN

N

O

Cl

Cl

O CH2C

CH


azafenidin 27

HRAC E WSSA 14; triazolinoneNOMENCLATURE:Common name azaf(nidine) ((f) F-ISO); azafenidin (BSI, E-ISO)IUPAC name 2-(2,4-dichloro-5-prop-2-ynyloxyphenyl)-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyridin-3(2H)-oneChemical Abstracts name 2-[2,4-dichloro-5-(2-propynyloxy)phenyl]-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyridin-3(2H)-one CAS RN [68049832] Development codes R6447; DPX-R6447; IN-R6447 (all DuPont) Smiles code Clc1cc(Cl)c(cc1OCC#C)n2nc3CCCCn3c2=OPHYSICAL CHEMISTRY:Composition Tech. isc. 97% pure. Mol. wt. 338.2 M.f. C15H13Cl2N3O2 Form White powdered solid; (tech. is a rust-coloured solid with a pungent odour). M.p. 168168.5 C V.p. 1 106 mPa (20 C) Kow logP = 2.7 S.g./density 1.4 (20 C) Solubility In water 16 ppm (pH 7). Stability Stable to hydrolysis; aqueous photolysis DT50 c. 12 h.COMMERCIALISATION:History Evaluated by E. I. du Pont de Nemours & Co. Reported by L. Amuti et al. (Proc. Br. Crop Prot. Conf. Weeds 1997, 1, p. 59).Manufacturers DuPontAPPLICATIONS:Biochemistry Protoporphyrinogen oxidase inhibitor. Mode of action Absorbed through the roots and shoots. Weakly xylem or phloem mobile, hence has limited post-emergence activity. However, it improves the efficacy of other post-emergence herbicides, such as glyphosate, and increases the speed of action of contact herbicides. Uses Intended for use as a pre-emergence, and, in mixture, post-emergence, herbicide in citrus, grapes, olives, sugar cane and other perennial crops; active on both annual and perennial weeds, and applied at 240 g/ha. Formulation types WG .PRODUCTS:Discontinued products Evolus* (Europe) (DuPont); Milestone* (USA) (DuPont).TOXICOLOGICAL & ENVIRONMENTAL REVIEWS:EU Status (1107/2009) Not approved, 2002/949/EC.MAMMALIAN TOXICOLOGY:Oral Acute oral LD50 for rats >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits >2000 mg/kg. Not an eye or skin irritant. Not a skin sensitiser. Inhalation LC50 for rats >5.3 mg/l. NOEL (90 d) for male and female rats 50, male mice 50, female mice 300, dogs 10 ppm. Other Negative in Ames test. ECClassification T; R48/22| R61, R62| N; R50, R53| concn. dep.ECOTOXICOLOGY:Birds Acute oral LD50 for bobwhite quail and mallard ducks >2250 mg/kg. LC50 (8 d) for bobwhite quail and mallard ducks >5620 ppm. Fish LC50 (96 h) for rainbow trout 33, bluegill sunfish 48 mg/l. Daphnia EC50 (48 h) 38 mg/l. Algae EC50 (120 h) for Selenastrum capricornutum 0.94 ;g/l. Bees LD50 (oral) >20 g/bee; (contact) >100 g/bee.

28


aziprotryne

ENVIRONMENTAL FATE:Soil/Environment Degrades in soil by microbial and photolytic processes. In the field, in a range of 4 soils, mean DT50c. 25 d, mean DT90c. 169 d. Mean Koc 298; there was minimal movement in soil column leaching studies and azafenidin is not expected to leach into groundwater. It is expected to dissipate rapidly through photolysis in natural waters. Details PM12, Entry 43.

aziprotryneHerbicide

NOMENCLATURE:Common name aziprotryne (BSI, E-ISO, (f) F-ISO); aziprotryn (USA)IUPAC name 4-azido-N-isopropyl-6-methylthio-1,3,5-triazin-2-ylamineChemical Abstracts name 4-azido-N-(1-methylethyl)-6-(methylthio)-1,3,5-triazin-2-amine CAS RN [4658280] Development codes C 7019 Smiles code CSc1nc(NC(C)C)nc(N=[N]=[N])n1PHYSICAL CHEMISTRY: Mol. wt. 225.3 M.f. C7H11N7S Form Colourless crystalline powder. M.p. 94.595.5 C V.p. 0.267 mPa (20 C) Henry 1.09 103 Pa m3 mol1 (calc.) S.g./density 1.40 (20 C) Solubility In water 55 mg/l (20 C). In acetone 27, dichloromethane 37, ethyl acetate 12, isopropanol 14, benzene 4 (all in g/kg, 20 C). Stability Stable in neutral and slightly acidic media. Hydrolysed slowly in slightly alkaline media.COMMERCIALISATION:History Herbicide reported by D. H. Green et al. (C. R. Journ. Etud. Herbic. Conf. COLUMA, 4th, 1967, 1, 1). Introduced by Ciba AG (later Novartis Crop Protection AG). Patents BE 656233; GB 1093376 Manufacturers NovartisAPPLICATIONS:Biochemistry Photosynthetic electron transport inhibitor at the photosystem II receptor site. Mode of action Selective herbicide, absorbed through the roots and foliage. Uses Control of a wide range of annual broad-leaved weeds and some grasses in brassicas (except cauliflowers), onions, leeks, garlic, shallots, fennel, peas, beans, black salsify, and oilseed rape. Applied pre- or post-emergence. Phytotoxicity Phytotoxic to cauliflowers. Formulation types WP.PRODUCTS:Discontinued products Brasoran* (Novartis); Mesoranil* (Ciba-Geigy).

N N

NCH3S NHCH(CH3)2

N3


azobenzene 29

ANALYSIS:Product analysis by glc. Residues determined by glc using MCD.TOXICOLOGICAL & ENVIRONMENTAL REVIEWS:EU Status (1107/2009) Not approved, Commission Regulation 2076/2002.MAMMALIAN TOXICOLOGY:Oral Acute oral LD50 for rats 36005833 mg/kg. Skin and eye Acute percutaneous LD50 for rats >3000 mg/kg. Mild eye irritant; non-irritating to skin. Inhalation LC50 (6 h) for rats >0.208 mg/l. NOEL (90 d) for rats 50 mg/kg daily; for dogs 50 mg/kg daily. Toxicity Class WHO (a.i.) U EPA (formulation) IIIECOTOXICOLOGY:Birds Dietary LC50 (8 d) for mallard ducks and quail >4000 mg/kg. Fish LC50 (96 h) for bluegill sunfish and largemouth bass >1 mg/l. Bees Not toxic to bees. Details PM9, Entry 0550.

azithiramFungicide

NOMENCLATURE:Common name azithiram (BSI, E-ISO); azithirame ((m) F-ISO)IUPAC name bis(3,3-dimethylthiocarbazoyl) disulfide; N,N-bis(dimethylamino)thiuram disulfideChemical Abstracts name 2,2,2,2-tetramethylthioperoxydicarbonic dihydrazide ([[(CH3)2NNH]C(S)]2S2) CAS RN [5834946] Development codes PP447 Smiles code CN(C)NC(=S)SSC(=S)NN(C)CPHYSICAL CHEMISTRY: Mol. wt. 270.5 M.f. C6H14N4S4COMMERCIALISATION:History Fungicide evaluated by ICI Plant Protection Division (later ICI Agrochemicals).

azobenzeneAcaricide

NOMENCLATURE:Common name azobenzene (BSI, E-ISO, F-ISO, accepted in lieu of a common name)IUPAC name azobenzeneChemical Abstracts name diphenyldiazene CAS RN [103333] Smiles code N(=Nc1ccccc1)c2ccccc2PHYSICAL CHEMISTRY: Mol. wt. 182.2 M.f. C12H10N2COMMERCIALISATION:History Acaricidal activity reported by W. E. Blauvelt (N. Y. State Flower Grow. Bull., 1945,

30


azoxybenzene

No. 2). Was mainly used in glasshouses as a smoke.MAMMALIAN TOXICOLOGY:ECClassification R45; R40| Xn; R20/22 R48/22| N; R50/53 Details PM4, p. 27.

azothoateAcaricide, insecticide

IRAC 1BNOMENCLATURE:Common name azothoate (BSI, E-ISO, (m) F-ISO)IUPAC name O-4-(4-chlorophenylazo)phenyl O,O-dimethyl phosphorothioateChemical Abstracts name O-[4-[(4-chlorophenyl)azo]phenyl] O,O-dimethyl phosphorothioate CAS RN [5834968] EC no 2274193 Development codes L 1058 Smiles code COP(=S)(OC)Oc1ccc(N=Nc2ccc(Cl)cc2)cc1PHYSICAL CHEMISTRY: Mol. wt. 356.8 M.f. C14H14ClN2O3PSCOMMERCIALISATION:History Insecticide and acaricide introduced by Montecatini S.p.A. (later Agrimont S.p.A.).APPLICATIONS:Biochemistry Cholinesterase inhibitor.TOXICOLOGICAL & ENVIRONMENTAL REVIEWS:EHC 63 (1986; a general review of organophosphorus insecticides).MAMMALIAN TOXICOLOGY:Toxicity Class WHO (a.i.) OECClassification Xn; R20/22

azoxybenzeneAcaricide, insecticide

NOMENCLATURE:IUPAC name azoxybenzeneChemical Abstracts name diphenyldiazene 1-oxide Other names fenazox CAS RN [495487] EC no 2078021PHYSICAL CHEMISTRY: Mol. wt. 198.2 M.f. C12H10N2O Form Pale yellow needles. M.p. 3838.5 C V.p. 13 mPa (20 C) S.g./density 1.159 (20 C) Solubility In water 3.4 mg/kg (25 C). In ethanol 285, groundnut oil 760 g/kg (26 C); in ligroin 435 g/kg (10 C). Stability Converted to o-hydroxyazobenzene by irradiation, and to p-hydroxyazobenzene in acidic media. Stable in strongly alkaline media.COMMERCIALISATION:Manufacturers Fahlberg-List


barban 31

APPLICATIONS:Mode of action Non-systemic, with contact action. Uses Control of mites and whitefly on fruit trees, vines, hops, soya beans, ornamentals, vegetables and glasshouse crops. Formulation types EC.PRODUCTS:Discontinued products Fentoxan* (Fahlberg-List).ANALYSIS:Product by glc with FID. Residues by tlc, or by glc with ECD.MAMMALIAN TOXICOLOGY:Oral Acute oral LD50 for rats 885 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits 1350 mg/kg. NOEL (90 d) for rats 1 mg/kg daily. Other Non-carcinogenic and non-mutagenic. ECClassification Xn; R20/22ECOTOXICOLOGY:Fish LC50 (96 h) for carp 3, rainbow trout 2.7 mg/l. Bees Not toxic to bees.ENVIRONMENTAL FATE:Plants Rapidly metabolised, initially to o-hydroxyazobenzene.

barbanHerbicide

NOMENCLATURE:Common name chlorinat* (former exception, USSR); CBN (JMAF); barbanate (Republic of South Africa); barbane ((m) F-ISO); barban (BSI, E-ISO, ANSI, WSSA)IUPAC name 4-chlorobut-2-ynyl 3-chlorocarbanilateChemical Abstracts name 4-chloro-2-butynyl (3-chlorophenyl)carbamate CAS RN [101279] EC no 2029304 Development codes CS-847 (Spencer Chemicals) Smiles code ClCC#CCOC(=O)Nc1cccc(Cl)c1PHYSICAL CHEMISTRY: Mol. wt. 258.1 M.f. C11H9Cl2NO2 Form Cystalline solid; (tech. is a tan solid). M.p. 7576 C; (tech., 60 C) V.p. 0.05 mPa (25 C) Henry 1.17 103 Pa m3 mol1 (calc.) S.g./density 1.403 (25 C, tech.) Solubility In water 11 mg/l (25 C). In benzene 327, 1,2-dichloroethane 546, hexane 1.4, kerosene 3.9, xylene 279 (all in g/l, 25 C). Stability Tech. decomposes at 224 C. Stable under normal conditions of use; hydrolysis is very rapid in alkali with displacement of the terminal chlorine substituent, DT50 58 sec (pH 13, 25 C).COMMERCIALISATION:History Herbicide reported by A. D. Brown (Proc. North Cent. Weed Control Conf., 1958, 15, 98). Introduced by the Spencer Chemical Co. and later Velsicol Chemical Corp. Patents US 2906614

32


barban

APPLICATIONS:Biochemistry Acts by interfering with cell division. Mode of action Selective herbicide, absorbed principally by the foliage, with limited translocation in the apoplast. Uses A selective post-em. herbicide controlling wild oats in barley at the 1.52.5 leaf stage, and broad beans, field flax, lentils, lucerne, mustard, oilseed rape, safflower, soya beans, sugar beet, sunflowers, wheat, Russian wild rye and other grasses. Phytotoxicity Phytotoxic to oats and some varieties of rye. Formulation types EC.PRODUCTS:Discontinued products B25* (FBC); Carbyne* (Spencer Chemicals).ANALYSIS:Product analysis by uv spectrometry (K. J. Bombaugh & W. C. Bull, J. Agric. Food Chem., 1961, 9, 386). Residues determined by hplc or by hydrolysis to 3-chloroaniline derivatives which are measured by glc (R. J. Harris & R. J. Whiteoak, Analyst (London), 1972, 97, 294). See also Pestic. Anal. Man., II, 180.268. In water, by lc with uv detection (AOAC Methods, 18th Ed., 992.14).TOXICOLOGICAL & ENVIRONMENTAL REVIEWS:EHC 64 (1986) is a general review of pesticides with a carbamate chemical structure. EU Status (1107/2009) Not approved, Commission Regulation 2076/2002.MAMMALIAN TOXICOLOGY:Oral Acute oral LD50 for rats 13761429 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits >20 000, rats >1600 mg/kg. Mildly irritating to the skin of rabbits and produces a delayed skin sensitisation in guinea-pigs. It has been reported as a skin sensitiser in man; skin contact should be avoided by using plastic protective clothing. Inhalation LC50 (4 h) for rats >28 mg/l air. NOEL (2 y) for rats 150 mg/kg diet, for dogs 5 mg/kg diet. In a 3-generation reproduction study in rats, NOEL 957 mg/kg diet Other Not teratogenic in rats at 87 mg/kg daily. Non-mutagenic to mammals by in vivo and in vitro tests. Toxicity Class WHO (a.i.) IIIECClassification Xn; R22| R43| N; R50, R53ECOTOXICOLOGY:Birds Dietary LC50 (8 d) for mallard ducks and bobwhite quail >10 000 mg/kg diet. Fish LC50 (96 h) for rainbow trout 0.6, bluegill sunfish 1.2, goldfish and guppies 1.3 mg/l. Bees Not toxic to bees.ENVIRONMENTAL FATE:Animals In rats and rabbits, barban is not easily absorbed through the skin. In rats, metabolism involves hydrolysis of the carbamate group, with formation of well known m-chloroaniline metabolites. There is no accumulation of barban or its metabolites in tissue, and they are rapidly excreted, principally in the urine. Plants Degraded rapidly in most plants. Metabolites include 3-chloroaniline and a glutathione conjugate. Soil/Environment In soil, degradation involves hydrolytic cleavage of the chlorobutynyl group, followed by decomposition of the carbamic acid so formed, with evolution of CO2, to give 3-chloroaniline. Duration of residual activity in soil, following an application rate of 3 l/ha, is c. 23 months. Details PM8, Entry 00620.


barium polysulfide 33

barium carbonateRodenticide

NOMENCLATURE:Common name barium carbonate (JMAF) IUPAC name barium carbonate (I)Chemical Abstracts name (I) CAS RN [513779] EC no 2081673 Smiles code [Ba+2].[O-]C(=O)[O-]PHYSICAL CHEMISTRY: Mol. wt. 197.3 M.f. CBaO3COMMERCIALISATION:History Used as a rodenticide for many years.MAMMALIAN TOXICOLOGY:Toxicity Class WHO (a.i.) OECClassification barium salts (with exceptions) are Xn; R20/22 (concentration-dependent) Details PM5, p. 28.

barium polysulfideFungicide, insecticide

NOMENCLATURE:Common name barium polysulfide (E-ISO, is accepted in lieu of a common name); polysulfure de baryum (F-ISO)IUPAC name barium polysulfide (I)Chemical Abstracts name (I) CAS RN [50864670]PHYSICAL CHEMISTRY:M.f. BaSxCOMMERCIALISATION:History Insecticide and fungicide introduced by Bayer AG.PRODUCTS:Discontinued products Florbario* (Sariaf); Solbar* (Bayer); Tiobar* (Farmoplant).TOXICOLOGICAL & ENVIRONMENTAL REVIEWS:EU Status (1107/2009) Not approved, Commission Regulation 2076/2002.MAMMALIAN TOXICOLOGY:ECClassification barium salts (with exceptions) are Xn; R20/22 (concentration-dependent)

34


Bayer 22/190

Bayer 22/190Insecticide

IRAC 1BNOMENCLATURE:IUPAC name O-3-chloro-4-nitrophenyl O,O-dimethyl phosphorothioateChemical Abstracts name O-(3-chloro-4-nitrophenyl) O,O-dimethyl phosphorothioate Other names chlorthion CAS RN [500287] EC no 2079025 Development codes Bayer 22/190 Smiles code COP(=S)(OC)Oc1ccc([N+](=O)[O-])c(Cl)c1PHYSICAL CHEMISTRY: Mol. wt. 297.7 M.f. C8H9ClNO5PS M.p. 21 C B.p. 136 C /0.3 mbar; 112 C /0.05 mbar V.p. 5.5 101 mPa (20 C) Henry 4.09 103 Pa m3 mol1 (calc.) S.g./density 1.433 (420 C) Solubility In water 40 mg/l (20 C). Readily soluble in common organic solvents with the exception of mineral oils. Stability Rapidly hydrolysed in alkaline media, more slowly in the presence of acids.COMMERCIALISATION:History Insecticide introduced by Bayer AG.APPLICATIONS:Biochemistry Cholinesterase inhibitor. Mode of action Insecticide with contact, stomach, and respiratory action. Uses Insecticidal control of aphids and sucking and biting insects in general in fruit, vine, and field cultivation and forestry, especially control of the mangold fly and sawfly. Phytotoxicity Phytotoxic to a few varieties of apple (e.g. McIntosh). Formulation types WP; DP .PRODUCTS:Discontinued products Chlorthion* (Bayer).ANALYSIS:Product by extraction with ether or petroluem ether, washing with 1% sodium carbonate solution, reduction of the nitro group with zinc dust in glacial acetic acid/hydrochloric acid (9:1), and titration of the amine with sodium nitrite and iodine-starch (WHO Specifications for Pesticide, 2nd edn, Geneva, 1961). Residues: depending on the moisture content of the sample, extraction with either acetone or chloroform, clean-up by liquid-liquid extraction or column chromatography, and gc determination with ECD (Man. Pestic. Residue Anal.,22). For colorimetric determination see Anal. Methods Pestic. Plant Growth Regul., 2,78, and for gc with ECD see Anal. Methods Pestic. Plant Growth Regul. 1972, 6, 322324.TOXICOLOGICAL & ENVIRONMENTAL REVIEWS:JMPR Evaln. 4 (1965).MAMMALIAN TOXICOLOGY:Oral Acute oral LD50 for rats 6251500 mg/kg. Skin and eye Acute percutaneous LD50 for rats 15004500 mg/kg. NOEL Administration of 10, 20, and 50 mg/kg diet for


Bayer 32394 35

120 d produces no histopathological changes, apart from cholinesterase inhibition at 10 mg/kg. ADI/RfD (JMPR) No ADI [1965] ECClassification Xn; R20/21/22| N; R50, R53| concn. dep.ECOTOXICOLOGY:Fish Toxic to fish and animals of fish diet. Bees Toxic to bees.ENVIRONMENTAL FATE:Soil/Environment Rapidly hydrolysed to dimethyl thiophosphate and 3-chloro-4-nitrophenol. To a limited extent, there is oxidation to the phosphate and hydrolysis to phosphoric acid and 3-chloronitrophenol.

Bayer 22408Insecticide

IRAC 1BNOMENCLATURE:IUPAC name O,O-diethyl naphthalene-1,8-dicarboximido-oxyphosphonothioate; O,O-diethyl naphthalimido-oxyphosphonothioate; N-diethoxyphosphinothioyl=oxynaphthalene-1,8-dicarboximideChemical Abstracts name 2-[(diethoxyphosphinothioyl)oxy]-1H-benz[de]isoquinoline-1,3(2H)-dione CAS RN [2668920] Development codes Bayer 22408; S 125 Smiles code CCOP(=S)(OCC)ON1C(=O)c2cccc3cccc(C1=O)c23PHYSICAL CHEMISTRY: Mol. wt. 365.3 M.f. C16H16NO5PSCOMMERCIALISATION:History Insecticide, discovered by W. Lorenz, evaluated by Bayer AG.APPLICATIONS:Biochemistry Cholinesterase inhibitor. Details PM1, p. 159.

Bayer 32394Fungicide

NOMENCLATURE:IUPAC name tris(1-dodecyl-3-methyl-2-phenylbenzimidazolium) hexacyanoferrateChemical Abstracts name tris[1-dodecyl-3-methyl-2-phenyl-1H-benzimidazolium] hexakis(cyano-C)ferrate CAS RN [7276586], formerly [64070979] and [16071899] Development codes Bayer 32394; B 169 Ferricyanide Smiles code CCCCCCCCCCCCn1c(c2ccccc2)[n+](C)c3ccccc13.CCCCCCCCCCCCn1c(c2ccccc2)[n+](C)c3ccccc13.CCCCCCCCCCCCn1c(c2ccccc2)[n+](C)c3ccccc13.N#C[Fe-3](C#N)(C#N)(C#N)(C#N)C#N

36


bencarbazone

PHYSICAL CHEMISTRY: Mol. wt. 1344.7 M.f. C84H111FeN12COMMERCIALISATION:History Fungicide introduced by Bayer AG.APPLICATIONS:Mode of action Protective fungicide.PRODUCTS:Discontinued products Fungilon* (Bayer). Details PM2, p. 213.

bencarbazoneHerbicide

NOMENCLATURE:Common name bencarbazone (BSI, E-ISO, (f) F-ISO)IUPAC name 4-[4,5-dihydro-4-methyl-5-oxo-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl]-2-[(ethylsulfonyl)amino]-5-fluorobenzenecarbothioamideChemical Abstracts name 4-[4,5-dihydro-4-methyl-5-oxo-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl]-2-[(ethylsulfonyl)amino]-5-fluorobenzenecarbothioamide CAS RN [173980171] Development codes TM-435; HWH 4991PHYSICAL CHEMISTRY: Mol. wt. 427.4 M.f. C13H13F4N5O3S2 Form Yellowish-grey powder. M.p. 202 C Kow logP = 0.179 (pH 7.5) Solubility In water 0.105 g/l (pH 7). Stability Hydrolysis DT50 >500 h (pH 4), 241 h (pH 7), 174 h (pH 9) (all at 50 C).COMMERCIALISATION:History Herbicide discovered by Bayer CropScience; licensed to Tomen Agro (later Arysta LifeScience Corporation) in 2001.APPLICATIONS: Uses Evaluated for post-emergence control of broad-leaved weeds in maize and cereals.MAMMALIAN TOXICOLOGY:Oral Acute oral LD50 for rats >2500 mg/kg. Skin and eye Not a skin or eye irritant. Is a skin sensitiser (guinea pigs). Inhalation LC50 (4 h) for rats >5045 mg/l. NOEL (13 w) for dogs 6 mg/kg.

CNH2S

F

NHSO2CH2CH3

NN

NCF3

O

CH3


benodanil 37

ECOTOXICOLOGY:Birds LD50 (14 d) for bobwhite quail >2000 mg/kg daily. Fish LC50 (96 h, static) for trout >100 mg/l. Daphnia EC50 (48 h, static) >10 mg/l. Algae IC50 (72 h, static) for Selenastrum capricornutum 2 mg/l. Worms LC50 (14 d) for earthworms >1000 mg/kg dry soil.

benclothiazNematicide

NOMENCLATURE:Common name benclothiaze ((m) F-ISO); benclothiaz (BSI, E-ISO)IUPAC name 7-chloro-1,2-benzothiazoleChemical Abstracts name 7-chloro-1,2-benzisothiazole CAS RN [89583904] Development codes CGA 235 860PHYSICAL CHEMISTRY: Mol. wt. 169.6 M.f. C7H4ClNSCOMMERCIALISATION:History Nematicide evaluated by Novartis AG.

benodanilFungicide

FRAC 7, C2

NOMENCLATURE:Common name benodanil (BSI, E-ISO, (m) F-ISO) IUPAC name 2-iodobenzanilideChemical Abstracts name 2-iodo-N-phenylbenzamide CAS RN [15310017] Development codes BAS 3170F (BASF) Smiles code Ic1ccccc1C(=O)Nc2ccccc2PHYSICAL CHEMISTRY: Mol. wt. 323.1 M.f. C13H10INO Form Colourless crystals. M.p. 137 C V.p.

38


benquinox

COMMERCIALISATION:History Fungicide reported by E. H. Pommer et al., at the 39th Deutsche Pflanzenschutztagung, Stuttgart, 1973 and by F. Lcher et al. (Meded. Fac. Landbouwwet. Rijksuniv. Gent, 1974, 39, 1079). Introduced by BASF AG.APPLICATIONS:Biochemistry SDHI: inhibits mitochondrial function by disrupting complex II (succinate dehydrogenase) in the respiratory electron transport chain. Mode of action Systemic and contact fungicide with protective and curative action. Uses Control of rust diseases of cereals, coffee, vegetables, and ornamentals; rust and fairy rings on turf; Rhizoctonia spp. on cotton, potatoes, cereals, rice, soya beans, ornamentals, vegetables, tobacco, and turf; and Typhula incarnata in cereals. Formulation types WP.PRODUCTS:Discontinued products Calirus* (BASF).ANALYSIS:Product by hplc. Residues by glc with ECD.TOXICOLOGICAL & ENVIRONMENTAL REVIEWS:EU Status (1107/2009) Not approved, Commission Regulation 2076/2002.MAMMALIAN TOXICOLOGY:Oral Acute oral LD50 for rats and guinea pigs >6400 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Non-irritating to skin and eyes (rabbits). NOEL (90 d) for rats >100 mg/kg diet. Toxicity Class WHO (a.i.) U EPA (formulation) IVECOTOXICOLOGY:Fish LC50 (96 h) for trout 6.4 mg/l. Bees Not toxic to bees.ENVIRONMENTAL FATE:Soil/Environment In loamy and humous sandy soils DT50 c. 34 weeks. Details PM8, Entry 00710.

benquinoxFungicide

NOMENCLATURE:Common name tserenox (USSR); benquinox (BSI, E-ISO, (m) F-ISO)IUPAC name 2-(4-hydroxyiminocyclohexa-2,5-dienylidene)benzohydrazide; 1,4-benzoquinone 1-benzoylhydrazone 4-oximeChemical Abstracts name benzoic acid [4-(hydroxyimino)-2,5-cyclohexadien-1-ylidene]hydrazide Other names COBH CAS RN [495738] EC no 2078079 Development codes Bayer 15 080 Smiles code ON=C1C=CC(=NNC(=O)c2ccccc2)C=C1PHYSICAL CHEMISTRY: Mol. wt. 241.3 M.f. C13H11N3O2 Form Yellow-brown crystals. M.p. 195 C (decomp.)


bentaluron 39

V.p. Non-volatile Solubility In water 5 mg/l (room temperature). Dissolves readily in aqueous alkalis with the formation of salts. Soluble in common organic solvents, readily soluble in formamide. Stability Very stable under normal conditions. Hydrolysed by strong acids and alkalis.COMMERCIALISATION:History Fungicide reported by P. E. Frohberger (Phytopath. Z., 1956, 37, 427). Introduced by Bayer AG.APPLICATIONS: Uses Fungicidal dressing to protect seeds and seedlings from soil fungi. Not used against cereal seed-borne diseases. Phytotoxicity Should not be used as a leaf fungicide.PRODUCTS:Discontinued products Ceredon* (Bayer); Cereline* (Bayer); Discontinued mixtures Ceredon T* (+ thiram) (Bayer); Rhizoctol combi* (+ methylarsenic sulfide) (Bayer); Rhizoctol slurry* (+ methylarsenic sulfide) (Bayer); Tillantox* (+ phenylmercury chloride) (Bayer).MAMMALIAN TOXICOLOGY:Oral Acute oral LD50 for ratsc. 100 mg/kg. Toxicity Class WHO (a.i.) O ECClassification T; R25| Xn; R21ECOTOXICOLOGY:Fish Toxic to fish. LC50 (48 h) for carp 0.048 mg/l. Bees Not known; irrelevant as regards the seed dressing agent. Details PM4, p. 35.

bentaluronFungicide

NOMENCLATURE:Common name bentaluron (BSI, E-ISO, (m) F-ISO) IUPAC name 1-(1,3-benzothiazol-2-yl)-3-isopropylurea; 1-benzothiazol-2-yl-3-isopropylureaChemical Abstracts name N-2-benzothiazolyl-N-(1-methylethyl)urea CAS RN [28956641] Development codes CGA 18 734 Smiles code CC(C)NC(=O)Nc1nc2ccccc2s1PHYSICAL CHEMISTRY: Mol. wt. 235.3 M.f. C11H13N3OSCOMMERCIALISATION:History Fungicide evaluated by Ciba AG (later Ciba-Geigy AG).TOXICOLOGICAL & ENVIRONMENTAL REVIEWS:EU Status (1107/2009) Not approved, Commission Regulation 2076/2002.

40


benzamorf

benzadox; benzadox-ammoniumHerbicide

NOMENCLATURE:Common name benzadox (BSI, ANSI, WSSA) IUPAC name benzamido-oxyacetic acidChemical Abstracts name [(benzoylamino)oxy]acetic acid CAS RN [5251934] benzadox Development codes MC 0035 (Murphy); S 6173 (Gulf) Smiles code benzadox:OC(=O)CONC(=O)c1ccccc1PHYSICAL CHEMISTRY: Mol. wt. 195.2; (ammonium salt 212.2) M.f. C9H9NO4; (ammonium salt C9H12N2O4)COMMERCIALISATION:History Herbicidal activity reported (Farm Chem., 1967, 130, 86). Introduced by Gulf Oil Corp. and by Murphy Chemical Co. (later DowElanco).PRODUCTS:Discontinued products Topcide* (Gulf). Details PM4, p. 38.

benzamacril; benzamacril-isobutylFungicide

NOMENCLATURE:Common name benzamacril (BSI, E-ISO, (m) F-ISO)IUPAC name 3-[benzyl(methyl)amino]-2-cyanoacrylic acid; 2-cyano-3-(N-methylbenzylamino)acrylic acidChemical Abstracts name 2-cyano-3-[methyl(phenyl)amino]-2-propenoic acid CAS RN [88107271] benzamacril-isobutyl; [127087869] benzamacril Smiles code benzamacril-isobutyl:CC(C)COC(=O)C(=CN(C)Cc1ccccc1)C#NPHYSICAL CHEMISTRY: Mol. wt. 216.2; (isobutyl ester 272.4) M.f. C12H12N2O2; (isobutyl ester C16H20N2O2)COMMERCIALISATION:History Fungicide evaluated by FBC Limited (later Schering Agriculture).

benzamorfFungicide

NOMENCLATURE:Common name benzamorf (BSI, E-ISO); benzamorphe ((m) F-ISO)IUPAC name morpholinium 4-dodecylbenzenesulfonate


benzfendizone 41

Chemical Abstracts name 4-dodecylbenzenesulfonic acid compound with morpholine (1:1) CAS RN [12068085] Development codes BAS 276F (BASF) Smiles code CCCCCCCCCCCCc1ccc(cc1)S(=O)(=O)[O-].C1COCC[NH2+]1PHYSICAL CHEMISTRY: Mol. wt. 413.6 M.f. C22H39NO4SCOMMERCIALISATION:History Fungicide introduced by BASF AG.APPLICATIONS:Mode of action Lipophilic fungicide.

benzfendizoneHerbicide

HRAC E WSSA 14; pyrimidindione

NOMENCLATURE:Common name benzfendizone (BSI, E-ISO, (f) F-ISO)IUPAC name methyl 2-{5-ethyl-2-[4-(1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-trifluoromethylpyrimidin-1-yl)phenoxymethyl]phenoxy}propionateChemical Abstracts name methyl 2-[2-[[4-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]phenoxy]methyl]-5-ethylphenoxy]propanoate CAS RN [158755954] Development codes FMC 143686; F3686 Smiles code CCc1ccc(COc2ccc(cc2)n3c(=O)cc(n(C)c3=O)C(F)(F)F)c(OC(C)C(=O)OC)c1PHYSICAL CHEMISTRY: Mol. wt. 506.5 M.f. C25H25F3N2O6COMMERCIALISATION:History Herbicide evaluated by FMC.APPLICATIONS:Biochemistry Inhibitor of protoporphyrinogen oxidase. Uses Evaluated for post-emergence control of grass and broad-leaved weeds in orchards and no-till situations; also as a cotton defoliant and potato desiccant. Details PM14, Entry 70.

NN

CH3CH2

O

O O

O

CH3

CF3CH3

CH3O2C

42


benzofluor

benzipramHerbicide

NOMENCLATURE:Common name benzipram (BSI, E-ISO, ANSI, WSSA); benziprame ((m) F-ISO)IUPAC name N-benzyl-N-isopropyl-3,5-dimethylbenzamideChemical Abstracts name 3,5-dimethyl-N-(1-methylethyl)-N-(phenylmethyl)benzamide CAS RN [35256861] Development codes S-18 510 Smiles code CC(C)N(Cc1ccccc1)C(=O)c2cc(C)cc(C)c2PHYSICAL CHEMISTRY: Mol. wt. 281.4 M.f. C19H23NOCOMMERCIALISATION:History Herbicide introduced by Gulf Oil Corp.

5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enoneInsecticide synergist

NOMENCLATURE:IUPAC name 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enoneChemical Abstracts name 5-(5-benzo-1,3-dioxolyl)-3-hexyl-2-cyclohexen-1-one Other names piperonyl cyclonene CAS RN [8066124]PHYSICAL CHEMISTRY: Mol. wt. 300.4 M.f. C19H24O3COMMERCIALISATION:History Synergist for insecticides.

benzofluorHerbicide

NOMENCLATURE:Common name benzofluor (BSI, ANSI, WSSA, E-ISO, (m) F-ISO)IUPAC name 4-ethylthio-2-(trifluoromethyl)methanesulfonanilide; 4-ethylthio-,,-trifluoromethanesulfon-o-toluidideChemical Abstracts name N-[4-(ethylthio)-2-(trifluoromethyl)phenyl]methanesulfonamide CAS RN [68672173] Development codes MBR 18 337 Smiles code CCSc1ccc(NS(=O)(=O)C)c(c1)C(F)(F)FPHYSICAL CHEMISTRY: Mol. wt. 299.3 M.f. C10H12F3NO2S2COMMERCIALISATION:History Herbicide and plant growth regulator introduced by 3M Company.


benzoylprop; benzoylprop-ethyl 43

benzoylprop; benzoylprop-ethylHerbicide

NOMENCLATURE:Common name benzoylprop (BSI, E-ISO, (m) F-ISO, WSSA)IUPAC name N-benzoyl-N-(3,4-dichlorophenyl)-DL-alanine (I)Chemical Abstracts name (I) CAS RN [22212551] benzoylprop-ethyl; [22212562] benzoylprop EC no 2448455 benzoylprop-ethyl Development codes WL 17 731 (ester)PHYSICAL CHEMISTRY:Composition Tech. is 93%. Mol. wt. 338.2; (ethyl ester 366.2) M.f. C16H13Cl2NO3; ethyl ester C18H17Cl2NO3 Form Tech. benzoylprop-ethyl is an off-white crystalline powder. M.p. 7071 C (ester) V.p. 0.0047 mPa (20 C, ester) Solubility In water c. 20 mg/l (25 C, ester). In acetone 700750, Shellsol A 250300 (both g/l, 25 C, for ester). Stability Stable photochemically, and hydrolytically over at least the range pH 3 to pH 6.COMMERCIALISATION:History Benzoylprop-ethyl is a herbicide reported by T. Chapman et al. (Symp. New. Herbic., 3rd, 1969, p. 40). Introduced by Shell Research Ltd. Patents GB 1164160APPLICATIONS:Mode of action Selective herbicide Uses Applied at 1.01.5 kg/ha to wheat, it gives an 8595% control of wild oat (Avena barbata, A. fatua, A. ludoviciana, A. sterilis). Field beans, oilseed rape and culinary mustard may also be safely treated. Crop competition ensures the effective control of wild oat, the stem elongation of which is inhibited (B. Jeffcoat & W. N. Harries, Pestic. Sci., 1973, 4, 891). Formulation types EC.PRODUCTS:Discontinued products Suffix* (Shell).ANALYSIS:Product analysis (ester) by glc (CIPAC Handbook, 1983, 1B, 1732) or by i.r. spectroscopy. Residues determined by glc with ECD (A. N. Wright & B. L. Mathews, Pestic. Sci., 1976, 7, 339).TOXICOLOGICAL & ENVIRONMENTAL REVIEWS:EU Status (1107/2009) Not approved, Commission Regulation 2076/2002.MAMMALIAN TOXICOLOGY:Oral Acute oral LD50 for rats 1555, for mice 716 mg/kg. Skin and eye Acute percutaneous LD50 for rats >1000 mg/kg. NOEL In 90 d feeding trials, no change of toxicological significance in rats receiving 1000 mg/kg diet or dogs 300 mg/kg diet. Toxicity Class WHO (a.i.) III (for ethyl ester)ECClassification Xn; R22| N; R50, R53 (for DL-benzoylprop-ethyl)ENVIRONMENTAL FATE:The fate of the compound in plants, soils and animals has been reported (K. I. Beynon et al.,

44


benzthiazuron

Pestic. Sci., 1974, 5, 429, 443, 451; J. V. Crayford et al., ibid., 1976, 7, 559). Details PM8, Entry 00850.

benzthiazuronHerbicide

NOMENCLATURE:Common name benzthiazuron (BSI, E-ISO, (m) F-ISO)IUPAC name 1-(1,3-benzothiazol-2-yl)-3-methylurea; 1-benzothiazol-2-yl-3-methylureaChemical Abstracts name N-2-benzothiazolyl-N-methylurea CAS RN [1929880] EC no 2176859 Development codes Bayer 60 618 Smiles code CNC(=O)Nc1nc2ccccc2s1PHYSICAL CHEMISTRY: Mol. wt. 207.3 M.f. C9H9N3OS Form Colourless powder. M.p. Decomposes (without melting) at 305-313 C V.p. 1.3 mPa (92 C, extrapolated) Solubility In water 15 mg/l (20 C). In organic solvents such as acetone, chlorobenzene, DMF, xylene, isobutanol 510 mg/l; dichloromethane 3, toluene 1, isopropanol 4 (all in g/l, 20 C). Stability Hydrolysed by strong acids and alkalis.COMMERCIALISATION:History Herbicide reported by H. Hack (International Meeting on Selective Weed Control in Sugar Beet Crops, Marly-le-Roi, 910 March 1967). Introduced in the Netherlands (1967) by Bayer AG. Patents BE 647740; GB 1004469APPLICATIONS:Biochemistry Photosynthetic electron transport inhibitor at the photosystem II receptor site. Interferes with cellular division at the level of RNA biosynthesis, and inhibits photosynthesis. Mode of action Selective herbicide, absorbed mainly by the roots. Uses Pre-emergence control of many germinating annual broad-leaved weeds in sugar beet, fodder beet, and spinach at 3.26.4 kg/ha. Formulation types WP. Compatibility Incompatible with quintozene and disulfoton.PRODUCTS:Discontinued products Gatnon* (Bayer).ANALYSIS:Product analysis by i.r. spectroscopy. Residues determined by uv spectroscopy (H. J. Jarczyk & K. Vogeler, Pflanz.-Nachr. Bayer (Engl. Ed.), 1967, 20, 575).TOXICOLOGICAL & ENVIRONMENTAL REVIEWS:EU Status (1107/2009) Not approved, Commission Regulation 2076/2002.

N

SNHCONHCH3


binapacryl 45

MAMMALIAN TOXICOLOGY:Oral Acute oral LD50 for male rats >2500, male mice >1000, male dogs >1000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >500 mg/kg. Irritating to eyes; non-irritating to skin. NOEL (90 d) for rats 1000 mg/kg. In 60 d feeding trials, rats receiving 130 mg/kg daily showed no ill-effects. Toxicity Class WHO (a.i.) III ECClassification Xn; R22ECOTOXICOLOGY:Fish Non-toxic to fish.ENVIRONMENTAL FATE:Soil/Environment Soil DT50 c. 1012 weeks. Details PM9, Entry 0860.

bethoxazinAlgicide, fungicide

NOMENCLATURE:Common name bethoxazine ((f) F-ISO); bethoxazin (BSI, E-ISO (not Japan))IUPAC name 3-benzo[b]thien-2-yl-5,6-dihydro-1,4,2-oxathiazine 4-oxideChemical Abstracts name 3-benzo[b]thien-2-yl-5,6-dihydro-1,4,2-oxathiazine 4-oxide CAS RN [163269305] EC no 4310306 Development codes R 102622 Smiles code O=S1C(C2=CC3=CC=CC=C3S2)=NOCC1PHYSICAL CHEMISTRY: Mol. wt. 251.3 M.f. C11H9NO2S2COMMERCIALISATION:Manufacturers Janssen

binapacrylAcaricide, fungicide

FRAC 29, C5; dinitrophenyl crotonateNOMENCLATURE:Common name binapacryl (BSI, E-ISO, (m) F-ISO, ANSI, ESA, JMAF)IUPAC name 2-sec-butyl-4,6-dinitrophenyl 3-methylbut-2-enoateChemical Abstracts name 2-(1-methylpropyl)-4,6-dinitrophenyl 3-methyl-2-butenoate CAS RN [485314] EC no 2076129 Development codes Hoe 02 784 Smiles

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