A World Compendium
`The Pesticide Manual
`I
`Seirenteenth Edition
`Editor: _J A Turner ___ -jJ'
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`SYNGENTA EXHIBIT 1011
`Syngenta v. UPL, PGR2023-00017
`
`

`

`- - - - - - - - - - - - ··-·----···· - - - - - - - - - - -
`
`A World Compendium
`
`T,he Pesticide Manual
`
`,{
`
`Seventeenth Edition
`Editor: J A Turner
`
`@BCPC
`
`Promoting the science and practice of sustainable crop production
`
`

`

`© 2015 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 978-1-901396-88-1
`
`.
`
`Thirteenth edition
`Fourteenth edition
`Fifteenth edition
`Sixteenth edition
`
`2003
`2006
`2009
`2012
`
`First published
`Second edition
`Third edition
`Fourth edition
`Fifth edition
`Sixth edition
`
`1968
`1971
`1972
`1974
`1977
`1979
`
`Seventh edition
`1983
`Eighth edition
`1987
`Ninth edilion
`1991
`Tenth edition*
`1994
`Eleventh edition
`1997
`Twelfth edition
`2000
`* The tenth edition incorporated The Agrochemicals Handbook, previously published by The Royal Society of
`Chemistry.
`
`Cover by the wright concept, www.thewrightconcept.co.uk and m360, www.m360.co.uk
`Typeset by Academic and Technical Typesetting, www.acadtech.co.uk
`Printed by Latimer Trend, latimertrend.com
`
`Published by: BCPC, 7 Omni Business Centre, Omega Park, Alton, Hampshire, GU34 2QD, UK
`t: +44 (0)1420 593 200
`www.bcpc.org
`
`All BCPC publications can be purchased from: BCPC Publications, 7 Omni Business Centre, Omega
`Park, Alton, Hampshire, GU34 2QD, UK
`t: +44 (0)1420 593 200
`e: publications@bcpc.org
`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.
`
`

`

`Contents
`
`Foreword
`The publisher
`Editorial Advisory Board
`Preface
`
`Introduction
`Guide to using the main entries
`Sample entry
`Notes to the sample entry
`
`I
`
`Main entries
`
`Supplementary entries
`
`Background
`Isomer nomenclature
`Resistance to pesticides
`Glossary of species
`Directory of companies
`Abbreviations and codes
`1 Common names - ISO and BSI recommended names for ions and radicals
`2 Formulation codes
`3 WIPO country codes for patents
`4 WHO toxicity classification
`5 EPA toxicity categories and pesticide label statements
`6 IOBC codes for beneficial species
`7 EC classification: risk symbols and phrases
`8 IARC carcinogenicity evidence classifications
`9 Drinking water Guideline Values (GV)
`10 General abbreviations
`Bibliography and references
`
`Indexes
`1 CAS Registry Numbers
`2 Molecular formulae
`3 General names
`4 Chemical classes
`
`iv
`
`V
`
`vi
`
`vii
`
`ix
`
`X
`xii
`
`1
`
`1183
`
`1219
`1222
`1223
`1239
`
`1251
`1251
`1253
`1253
`1254
`1254
`1255
`1257
`1258
`1258
`1265
`
`1271
`1282
`1299
`1351
`
`iii
`
`

`

`Foreword
`
`This seventeenth edition of The Pesticide Manual continues as an encyclopedic
`compendium of the chemistry, properties, targets and uses, toxicological and
`ecotoxicological properties of chemical pesticides. It provides a
`comprehensive -range of pertinent information at your fingertips, all in one
`document. The Pesticide Manual continues to be an indispensable tool for
`academics, pest control advisors and operators, manufacturers, students and
`regulators.
`
`The· number, types and properties of the compounds described in this latest edition - both current
`and discontinued - is testament to how pesiicide chemistry has evolved. For example. synthetic
`organic insecticides began with DDT, chlordane and parathion in the 1940s, followed by additional
`cyclodienes, organophosphates and carbamates in the 1950s. Negative aspects such as environmental
`persistence, mammalian toxicity and the development of resistance meant that many of these
`compounds were succeeded by the photostable synthetic pyrethroids; low rates of use and improved
`mammalian toxicity drove wide-scale use, particularly in agriculture, and the neonicotiniods, with
`their systemic properties, have followed in their wake as resistance inevitably developed. Similar
`trends have also driven innovation in fungicides and herbicides.
`
`As time progressed, a burgeoning chemical arsenal of pest, weed and disease control agents has been
`introduced, encompassing new modes of action and biochemical targets, increasingly sophisticated in
`terms of potency, selectivity and environmental impact, with more novel compounds in development.
`In all pesticide sectors, we have progressed from applying kg/hectare to gm/hectare of active
`ingredients. Chemical technologies continue to dominate, despite improvements in biopesticides.
`
`The need for existing and new pesticides has never been greater. Increasing world population and the
`requirement for plant- and animal-based food sources grows exponentially. The amount of arable
`land is essentially fixed, requiring ever greater efficiencies in terms of land use and inputs, including
`pesticides. Aquaculture, replacing wild fish and shellfish for human consumption, and worldwide
`efforts to reduce insect-borne diseases such as malaria, also require new pesticides. Public opinion, in
`turn influencing regulatory pressures, and the development of resistance, threaten some of our most
`important agricultural and horticultural insecticides, herbicides and fungicides.
`
`The Pesticide Manual continues as a unique illustration of the continued evolution and success of
`science in meeting these increasing demands.
`
`Professor Jeffrey'R Bloomquist
`Department of Entomology and Nema,tology
`Emerging Pathogens-rn"stitute
`University of Florida
`Gainesville, FL
`USA
`
`iv
`
`

`

`The publisher
`
`This seventeenth edition of The Pesticide Manual is published by BCPC, a registered charity, formed in
`1967. The principal aim oLBCPC is 'to promote and encourage the science and practice of crop
`production for the benefit of all'.
`
`BCPC brings together a wide range of orgarisations interested in the improvement of crop production.
`The members of its Committees and Working Groups represent the interests of government
`departments, the agrochemical industry, farmers' and consumers' organisations, the advisory
`services and independent consultants, distributors, the research councils, agricultural engineers,
`environment interests, training and overseas development.
`'
`'
`The corporate members of BCPC currently are:
`
`•
`ADAS*
`Agricultural Biotechnology Council (ABC)*
`Agricultural Industries Confederation (AIC)*
`Agriculture and Horticulture Development Board (AHDB) (HGCA, HDC, Potato Council)*
`Association of Applied Biologists (AAB)
`Association of Independent Crop Consultants (AICC)
`Biotechnology and Biological Sciences Research Council (BBSRC)
`British Institute of Agricultural Consultants (BlAC)
`Chemicals Regulation Directorate (Health and Safety Executive)
`Crop Protection Association (CPA)*
`Department of Environment, Food and Rural Affairs (Defra)*
`Environment Agency*
`Farming and Countryside Education (FACE)
`Game & Wildlife Conservation Trust
`National Farmers' Union (NFU)*
`National Institute of Agricultural Botany/The Arable Group (NIAB/TAG)*
`Processors and Growers Research Organisation (PGRO)
`Rothamsted Research
`Royal Agricultural Society of England (RASE)
`*Also on BCPC Advisory Council
`
`To obtain further information about BCPC, its activities, conferences or publications, please contact:
`
`The General Manager, BCPC, 7 Omni Business Centre, Omega Park, Alton,
`Hampshire GU34 2QD, UK
`t: +44 (0) 1420 593 200
`f: +44 (0) 1420 593 209
`e: md@bcpc.org
`w: www.bcpc.org
`
`V
`
`

`

`1
`
`V:
`
`Editorial Advisory Board
`
`The Editor is grateful for the contributions and advice of the BCPC Manuals Editorial Advisory Board:
`
`Richard Bromilow, formerly Visiting Scientist, Biological Chemistry Division, Rothamsted Research
`Peter Chapman, Director of Regulatory Affairs, JSC International Limited
`Roma Gwynn, Consultant, Rationale Biopesticide Strategists; Editor, The Manual of Biocontrol Agents
`Graham Jellis, Honorary Professor in Applied Plant Pa:thology, Nottingham University
`[ formerly President, British Society for Plant Pathology]
`Martin Lainsbury, Editor, The UK Pesticide Guide and The GM Crop Manual
`John Pickett, Michael Elliott Distinguished Research Fellow, Rothamsted Research
`Clive Rainbird, formerly Editor, The GM Crop Manual
`Colin Ruscoe, Chairman, BCPC; Communications Director, SynTech Research; Scientific
`Committee, Innovative Vector Contr<lll Consortium
`Mark Tatchell, Consultant [formerly Research Director, Warwick HRI and Chair Red Tractor Farm
`Assurance Fresh Produce Scheme]
`
`vi
`
`

`

`Preface
`
`The field of pesticide science continues to undergo extensive change. Industry consolidations advance.
`Discovery and manufacturing are ever more global. New tools are introduced for generation and sharing
`of data and information. Regulatory actions shape industry directions and farmer practices. Most
`importantly, innovative new pesticides continue to be discovered and developed - materials with exciting
`new properties and capabilities that continue to enhance worldwide crop production. This new
`seventeenth edition of The Pesticide Manual has been significantly upgraded to embrace these mega(cid:173)
`trends and to augment its role and value as a resource for the field at large. So users will now find an
`unprecedented number of new and improved features.
`
`Many data fields have now been revised to imp~ove ,consistency of data presentation and thus enhance
`property comparisons. Of particular note, the Physical Chemistry section has been completely
`revamped, standardising the units used for various physical properties ( e.g. mg/l for water solubility) and
`removing unit designators, data qualifiers and mher extraneous information from the entries. In a similar
`fashion, the format and units used for mammalian toxicological properties have been standardised (e.g.
`LDso in mg/kg b.w. for acute oral toxicity), and the former Skin and Eye section has been separated into
`three distinct fields in order to improve clarity.
`
`For those pesticides that exist as structural or isomeric mixtures, The Pesticide Manual now individually
`identifies the components (where relevant), complete with their IUPAC and/or CAS names, CAS RN
`and any physical chemistry or toxicological properties associated with each entity.
`
`The Nomenclature section has been revised, updating the IUPAC and CP,S names to current standards as
`well as including active ingredient Trademark names. In particular the entire class of synthetic pyrethroids
`has been reviewed with updated names, clarified isomeric composition and redrawn structures to
`conform to modern standards and trends.
`
`This edition builds significantly on the explosive growth of the internet as a major source of pesticide
`information. Where feasible, references to online data sources have been provided so the user can
`explore for more recent changes or additions. Company contact information has been replaced in The
`Pesticide Manual with website addresses; such links allow the user to find the most current and accurate
`details regarding company status, locations, contacts, products, subsidiaries or joint ventures and name
`changes.
`
`These modifications will be of particular value to users of the Online Pestidde Manual (bcpcdatacom/pm) .
`. The searching capability of the online version facilitates speedy retrieval of data on individual compounds
`or groups of pesticides. The enhancements noted above simplify the comparison of properties among
`the selected sets of pesticides. Further, the Online Pesticide Manual includes direct links to company
`websites, on line databases, and other useful references and resources ( e.g. Resistance Action Committee
`websites) as well as full details of Supplementary entries.
`
`..
`
`As always, this edition includes information on all new pesticides - the over 45 new active ingredients
`introduced worldwide since the previous edition.
`
`There has been one further rationalisation of content with this edition. The extremely fast-growing range of
`macro- and micro-biological organisms, botanicals and semiochemicals now being used in crop protection
`has made it appropriate that they are included in a separate publication. They are now covered, and with
`considerable added detail, in BCPC's Manual of Biocontrol Agents, edited by Dr Roma Gwynn (bcpcdata.
`com/mba).
`
`I have been blessed with extraordinarily competent assistance in the preparation of this new edition of
`The Pesticide Manual. Philip Mann has served as steward of the database and is a genius at retrieval of
`obscure information in any needed format. Andrew Mason has developed an amazingly intuitive content
`management system which allows for simplified input, retrieval and visualisation of data. Thanks go to
`Quentin Scott for his excellent and painstaking work checking the proofs; Tom Garland, Alan Bond and
`all at Academic and Technical Typesetting; and Paul Opie and all at Latimer Trend for printing. My
`
`vii
`
`

`

`colleagues at BCPC, particularly Dr Colin Ruscoe, Julian Westaway and Chris Todd, as well as members of
`the Editorial Advisory Board, have generously provided support, encouragement and sage advice on many
`subjects. Finally, I want to extend my sincerest thanks to Anne Sweetmore, Publications Project Manager, for
`cheerfully and diligently guiding me through the many details of the editorial and publication process. I am
`very grateful to those who, over the years, have contributed information on products on behalf of their
`Companies. This reference relies on such generosity to ensure the data is of the highest standard.
`
`The Pesticide Manual strives for perfection but recognises real-world limitations. The editor (pm@bcpc.org)
`welcomes reports of any errors or omissions. Corrections will be made in a timely manner to the online
`version of The Pesticide Manual.
`
`Dr James A. Turner
`Editor
`
`viii
`
`

`

`ENVIRONMENTAL FATE: Animals Metabolised by hydrolysis, forming 1,2,4-triazole and
`tricyclohexyl tin hydroxide, which is further oxidised to form dicyclohexyl tin oxide.
`Plants Metabolites identified in plants include 1,2,4-triazole, tricydohexyl tin hydroxide, and
`dicyclohexyl tin oxide. Soil/Environment Half-life in soil ranges from a few days to many weeks,
`depending on soil type.
`
`48 azoxystrobin
`
`FRAC 11, C3 Qol; strobi/urin type: methoxyacrylate
`
`Fungicide'
`
`NOMENCLATURE: Common name azoxystrobine ((f) F-1S0); azoxystrobin (BSI, E-1S0)
`IUPAC name methyl (2£)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate
`Chemical Abstracts name methyl (aE)-2-[[6-(2-cyanophenoxy)-4-pyrimidinyl]oxy]-a(cid:173)
`(methoxymethylene)benzeneacetate
`CAS RN [131860-33-8] Development codes IClA5504 (!Cl)
`PHYSICAL CHEMISTRY: Composition Tech. is >93%, with :,,;2.5% (Z)- isomer.
`Mot. wt. 403.4 M.f. C22H17N 30 5 Physical form White crystalline powder. M.p. {°C) 116
`B.p. >345 °C/760 mmHg V.p. (mPa) 1.1 x 10-7 (20 °C)
`0 log K0 w 2.5
`Henry (Pa m3 mol-1, calc.) 7.4 x 10-9 S.g./Bulk density (20-25 °C) 1.34
`Water solubility (mg/~ 20-25 °C) 6.7 (pH 7) Organic solubility (g/1, 20-25 °C) Soluble in
`acetone (86), acetonitrile (340), dichloromethane (400), ethyl acetate (130), hexane (0.057),
`n-octanol (1.4), methanol (20), toluene (55) Stability DT 50 8.7-13.9 d. at pH7 for aqueous
`photolysis
`COMMERCIALISATION: History Reported by J. R. Godwin et al. (Proc. Br. Crop Prot Conf. -
`Pests Dis., 1992, 1, 435). Introduced by Zeneca Agrochemicals (now Syngenta AG) and first
`marketed in 1996. Manufacturers Cheminova; Jiangsu Inter-China Group Corporation; Syngenta;
`Yongan Patents EP 382375.
`APPLICATIONS: Site of action Quinone outside inhibitor. Inhibits mitochondria\ respiration
`by blocking electron transfer between cytochrome b and cytochrome c1, at the ubiquinoi oxidising '
`site. Controls pathogenic strains resistant to the 14-demethylase inhibitors, phenylamides,
`dicarboxamides or benzimidazoles. Spectrum and route of action Fungicide with protectant,
`curative, eradicant, translaminar and systemic properties. Inhibits spore germination and mycelial
`growth, and also shows antisporulant activity. Uses Controls the following pathogens, at
`application rates between 100 to 375 g/ha: Erysiphe graminis, Puccinia spp., Leptosphaeria nodorum,
`Septoria tritici and Pyrenophora teres on temperate cereals; Pyricularia oryzae and Rhizoetonia so(ani on
`rice; Plasmopara viticola and Uncinula necator on vines; Sphaerotheca fuliginea and Pseudoperonospora
`cubensis on cucurbitaceae; Phytophthora infestans and Alternaria solani on potato and tomato;
`Mycosphaerella arachidis, Rhizoctonia solani and Sclerotium rolfsii on peanut; Monilinia spp. and
`Cladosporium carpophilum on peach; Pythium spp. and Rhizoctonia soloni on turf; Mycosphaerella
`spp. on banana; Cladosporium caryigenum on pecan; Elsinoe fawcettii, CoUetotrichum spp. and
`
`..
`
`66
`
`azoxystrobin
`
`

`

`Guignardia citricarpa on citrus; Col(etotrichum spp. and Hemileiavastatrix on coffee.
`Phytotoxicity Good crop safety, except on some varieties of apple (e.g. McIntosh, Cox).
`formulation types WG; SE; GR; SC Selected products Amistar (Syngenta); Heritage
`(Syngenta); Ortiva (Syngenta); Saphyr (Aako) Selected mixtures Elatus (Syngenta); Quadris
`(Syngenta); Reflect Xtra (Syngenta)
`ANALYSIS: Residues by gc/NPD (Resid. AnaL Methods) or le/ms/ms. Residues in water by hplc/
`uv (Environ. Chem. Methods). Residues in soil by hplc/uv, or by gc/ms (ibid.).
`TOXICOLOGICAL & ENVIRONMENTAL REVIEWS: JMPR Evaln. I 114 (2008);JMPR Evaln.
`II 115 (2008). EU Rev. Rep. 7581Nl/97, Apr. 1998; 11027/2011, June 2011. EPA Fact Sheet,
`Feb. 1997, EFSAJou. 2010, 8(4), 1542 [110 pp.]. EU status (1107/2009) Approved
`Legislation (EU) 703/2011, (EU) 540/2011) •
`MAMMALIAN'TOXICOLOGY: Acute oral (LDso, mg/kg) male and female rats >5000,
`male and female mice >5000 Acute perctitaneous (LD50, mg/l<g) rats >2000
`Skin irritation Slight irritant (rabbits). Skin sensitisation Not a sensitiser (guinea pigs).
`Eye Slight irritant (rabbits).
`Inhalation (LC 50, mg/I) male rats 0.96, female rats 0.69 (4 h) (nose
`exposure) NOEL (2 y) for rats 1.8 mg/kg b.w. daily. ADI/RID (JMPR) 0.2 mg/kg b.w.
`[proposed]; (EC) 0.1 mg/kg b.w. [1998]; (EPA) RID 0.18 mg/kg b.w. [1997].
`Toxicity class: WHO (a.i.) U EC classification T; R23I N; R50, R53 Other Not genotoxic,
`carcinogenic or neurotoxic; azoxystrobin has no effect on fertility parameters nor on foetal or
`infant development.
`ECOTOXICOLOGY: Birds Acute oral LDso for mallard ducks and bobwhite quail
`> 2000 mg/kg. Dietary LCso (5 d) for bobwhite quail and mallard ducks > 5200 mg/kg diet.
`fish LCso (96 h) for rainbow trout 0.47, bluegill sunfish 1.1, carp 1.6, sheepshead minnows
`0.66 mg/I. Daphnia EC50 (48 h) 0.28 mg/l. Algae EC50 (72 h) for Pseudokirchneriella subcapitata
`0.18 mg/I; EC50 (72 h) for diatom Navicula pefliculosa 0.028 mg/I. Ct.her aquatic spp. LC50 (96 h)
`for mysid shrimps 0.055 mg/l; EC50 (48 h) for Pacific oysters 1.3 mgll; EC50 (14 d) for Lemna gibba
`3.2mg/l; NOEC (25 d) for chironomid larvae 0.2mg/l. Bees (LD50, mg/bee) >25 (oral); >200
`(contact) Worms LC50 (14 d) for earthworms 283 mg/kg. Other beneficial spp. LR50 for
`predatory mites Typhlodromus pyri > 1500 g/ha; LR50 for parasitoid wasps Aphidius rhopalosiphi
`>1000 g/ha.
`
`ENVIRONMENTAL FATE: Animals In rats, the majority of radiolabel is excreted in the
`faeces, with little remaining radioactivity in any tissues of the animal. A large number of
`metabolites were formed, of which only the g!ucuronide of azoxystrobin acid is present at > 10%
`of the administered dose. In goats and hens, azoxystrobin is also excreted rapidly, with low
`residues in milk, meat or eggs. For details, see R. S. I. Joseph in Pestic. Chem. & Biosci. '"Plants ln
`wheat, grapes and peanuts, metabolism was extensive, but parent azoxystrobin was the only major
`(> 10%) residue. Metabolism followed similar pathways in all three crops. Soil/Environment In
`soil, DT 50 (lab.) 70 d (geometric mean; normalised to 20 °C, pF2; SFO kinetics). In soil, in the
`dark, up to six identified metabolites were formed; over 120 d, up to 27% of applied radiolabel is
`evolved as CO2• Dissipation in the field is faster; DT50 (geometric mean; SFO) 28 d, DT90 94 d
`(best fit, HS kinetics: DT50 13 d, DT90 236 d). On soil, photolysis DT50 11 d. Azoxystrobin is
`classified as moderately mobile in soi~ average K1oc for azoxystrobin c. 430. Field dissipation studies
`showed that neither azoxystrobin nor its major degradates were typically found in soil below the
`top 15 cm. In water-sediment systems (lab., 20 °C, dark), water phase ave. DT 50 6.1 d (SFO), total
`system ave. DT 50 214 d (SFO). Degradation in atmosphere occurs by reaction with hydroxyl
`radicals (AOP model), DT50 2.7h.
`
`azoxystrobin
`
`6 7
`
`

`

`66 benzovindiflupyr
`
`FRAC 7, C2 SDHI: pyrazo{ecarboxamide
`
`Fungicide
`
`NOMENCLATURE: Common name benzovindiflupyr (pa ISO)
`IUPAC name N-[(1 RS,4SR)-9-( dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-
`yl ]-3-( difluoromethyl)-1-methylpyrazole-4-carboxamide
`Chemical Abstracts name N-[9-( dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-
`5-yl]-3-( difluoromethyl)-1-methyl-1 H-pyrazole-4-carboxamide
`CAS RN [1072957-71-1] Development codes SYN545192
`Trademark name Solatenol
`PHYSICAL CHEMISTRY: Mol. wt. 398.2 M.f. C18H15ChF2N3O Physical form Off-white
`powder M.p. (°C) 148.4 B.p. Decomp. > 285 °C V.p. (mPa) 3.2 x 10-6 (25 °C)
`log K0w 4.3 Henry (Pa m3 mol-1, calc.) 1.3 x 10-6 S.g./Bulk density (20-25 °C) 1.466
`Water solubility (mg/I, 20-25 °C) 0.98 Organic solubility (g/1, 20~25 °C) Soluble in acetone
`(350), dichloromethane (450), ethyl acetate (190), hexane (270), methanol (76), octanol (19),
`toluene (48) Stability No degradation at pH 4, 5, 7, 9 for 5 d at 50 °C; hydrolytically stable for
`30 d at 25 °C.
`COMMERCIALISATION: History Developed by Syngenta AG. First sold in Paraguay in 2012.
`Manufacturers Syngenta Patents EP 1940813, US 7732469.
`APPLICATIONS: Site of action Succinate dehydrogenase inhibitor.
`Spectrum and route of action A pyrazole carboxamide fungicide belonging to the sub-class of
`the benzonorbornenes. Uses Controls (75 g/ha) soybean rust; Septoria tritici, Puccinia striiformis,
`Puccinia recondita on wheat; Puccinia hordei, Ramu/aria ca/lo-cygni, Rhynchosporium secalis ori"barley;
`Venturia inaequalis on pome fruits; early blight on potatoes; powdery mildew, early blight,
`anthracnose on vegetables; Puccinia sorghi, Cercospora zea-maydis on corn; Puccinia arachidis,
`sclerotium rolfsii on peanuts; Uncinula necotor on grapes. Formulation types EC; WG
`Selected products Aprovia (Syngenta) Selected mixtures Aprovia Top (Syngenta); Elatus
`(Syngenta)
`TOXICOLOGICAL & ENVIRONMENTAL REVIEWS: EU DAR, May. 2014
`EU status (1107/2009) Pending
`MAMMALIAN TOXICOLOGY: Acute oral (LD50, mg/kg) rats 55
`Acute percutaneous (LD50, mg/kg) rats > 2000 Skin irritation Not an irritant.
`Skin sensitisation Not a sensitiser. Eye Not an irritant.
`Inhalation (LC 5o, mg/I) rats 0.56
`NOEL rats (2 y) 4.88 mg/kg b.w., mice (80 w) 7.55 ADI/RID 0.05 mg/kg
`EC classification Danger. H301, H331, H410
`
`benzovindiflupyr
`
`9 3
`
`ift
`
`:•1·
`
`ii\
`
`1,
`
`

`

`ECOTOXICOLOGY: Birds Acute LD50 for bobwhite quail 1315 mg/kg b.w.; short-term LC50
`for bobwhite quail >1168mg/kg b.w., for mallard ducks >2761 Fish LC50 (96 h) for rainbow
`trout 0.0091 mg/I, for carp 0.0035 for fathead minnows 0.0047, for sheepshead minnows 0.027, for
`bluegill 0.026 Daphnia EC50 (48 h) 0.085 mg/I Algae EbCsa, ErCsa, EyCsa (72 h) for
`Pseudokirchneriella subcapitata >0.89 mg/I; EbC50 (72 h) for Ske/etonema costatum 0.45, ErCso 0.55,
`EyC50 0.47 Other aquatic spp. EC50 (7 d) for Lemna gibba >0.88 mg/I
`Bees (LD50, mg/bee) >109 (oral); >100 (contact) Worms LC50 (14 d) for earthworms.
`406.3 mg/kg dry soil
`ENVIRONMENTAL FATE: Animals Widely distributed, extensively metabolised and rapidly
`eliminated, with the majority of radioactivity being excreted within 72 h, mainly via faeces ( oral
`administration to rats). Extent of oral absorption in intact animals is estimated to be app. 60% of
`administered dose. Does not show any'potential for bioaccumulation. Plants Unchanged
`benzovindiflupyr accounted for a significant proportion of the residue in tomatoes, wheat and
`soybean; major metabolites included g:lemethylation of the pyrazole ring and hydroxylation of the
`alicyclic ring system. Soil/Environment Laboratory soil studies indicate that degradation in the
`dark is slow ( extrapolated DT50 > 1 y) and mobility is slight to immobile. Soil photolysis is slow
`and unlikely to be a significant environmental dissipation mechanism. Faster dissipation is observed
`under field conditions and DTSO values from trials in US and EU range from 116 to 614 d.
`Degradation in soil is due to microbial processes. In water-sediment systems under dark
`laboratory conditions DT50 for dissipation from the water phase was 14 to 25 d, however
`degradation was slow ( extrapolated DTSO > 1 y). Water-sediment studies incubated in a
`light-dark cycle with growing algae and macrophytes indicate that degradation is faster under
`realistic aquatic conditions (total system DTSO range 19 to 85 d).
`
`67 benzoxi mate
`
`IRAC UN
`
`Acaricide
`
`NOMENCLATURE: Common name benzoximate (BS!, E-1S0, (m) F-1S0); benzomate (JMAF)
`IUPAC name 3-chloro-a-ethoxyimino-2,6-dimethoxybenzyl benzoate; ethyl O-benzoyl-3-chloro-
`2,6-dimethoxybenzohydroximate
`Chemical Abstracts name benzoic acid anhydride with 3-chloro-N-ethoxy-2,6-
`dimethoxybenzenecarboximidic acid
`CAS RN [29104-30-1] EC no. 249-439-1 Development codes NA-53M (Nippon Soda)
`PHYSICAL CHEMISTRY: Mol. wt, 363.8 M.f. C 18H 18ClN05 Physical form Colourless
`crystals. M.p. (°C) 73 V.p. (mPa) 0.45 (25 °C)
`log K0 w 2.4
`Henry (Pa m3 mol-1, calc.) 0.00546 S.g./Bulk density (20-25 °C) 1.3
`Water solubility (mg/I, 20-25 °C) 30.0 Organic solubility (g/1, 20-25 °C) Soluble in benzene
`(650), DMF (1460), hexane (80), xylene (710) Stability Stable in acidic media, but decomposed
`by concentrated alkalis.
`
`94
`
`benzoximate
`
`

`

`./
`
`;;TOXICOLOGICAL & ENVIRONMENTAL REVIEWS: See A J. Gray & D. M. Soderlund,
`\chapt. 5 in Insecticides.
`)MAMMALIAN TOXICOLOGY: Acute oral (LD50, mg/kg) male rats 318, female rats 419
`§!(in corn oil) Acute percutaneous (LD50, mg/kg) rats >5000 Skin irritation Not an irritant.
`(,Eye Not an irritant.
`Inhalation (LC5o, mg/I) rats >1.85 (3 h) Toxicity class: WHO (a.i.) II
`)Toxicity class: EPA (formulation) II
`:iecOTOXICOLOGY: Birds Dietary LC50 for bobwhite quail >5620 ppm. Fish LC50 (96 h)
`\for rainbow trout 0.00034 mg/l.
`}ENVIRONMENTAL FATE: SoiUEnvironment Degradation involves ester hydrolysis and
`
`;\{\
`''~?200
`
`cyproconazole
`
`SB/ Class I, DMI: triazole Cl-o-~ f>H CH3
`,._ ?--dH
`\7
`yH2
`..,N';-,
`N\\_~
`
`Fungicide
`
`l~OMENCLATURE: Common name cyproconazole (BSI, E-1SO, (m) F-1SO, not Canada)
`\ IUPAC name (2RS,3RS:2RS,3SR)-2-( 4-chlorophenyl)-3-cyclopropyl-1-(1 H-1,2,4-triazol-1-yl)butan-2-
`§fr,1
`!{Chemical Abstracts name a-( 4-chlorophenyl)-a-(1-cyclopropylethyl)-1 H-1,2,4-triazol-1-ethanol
`\CAS RN [94361-06-5] Development codes SAN 619 F (Sandoz)
`"fl'HYSICAL CHEMISTRY: Composition 1: 1 Mixture of two diastereoisomers.
`'cl11ol. wt. 291.8 M.f. C15H18ClN3O F.p. >360°C Physical form Colourless solid.
`/l'!.p. {0q 106.2-106.9 B.p. > 250 °C/760 mmHg V.p. (mPa) 0.026 (25 °C)
`log l<ow 3.1
`Yl--lenry (Pa m3 mot-1, calc.) 5 x 10-5 (meas.) S.g./Bulk density (20-25 °C) Bulk d,msity:
`iJ:25 g/cm3 Water solubility (mg/I, 20-25 °C} 93.0
`/Organic solubility (g/l, 20-25 "C) Soluble in acetone (360), dichloromethane (430), DMSO
`{(180), ethanol (230), ethyl acetate (240), hexane (1.3), methanol (410), octanol (100), toluene
`(100), xylene (120) Stability Oxidative decomposition starts at c. 115 °C, followed by thermal
`:\clecomposition starting at c. 300 •c. Hydrolytically stable between pH 4 and 9, at 50 °C, for
`}§days.
`6
`[:'?0MMERCIALISATION: History Fungicide reported by U. Gisi et al. (Proc. Br. Crop Prot Conf.,
`}1,?86, 1, 33; 2, 857). Introduced in France and Switzerland (1989) by Sandoz AG (now Syngenta
`\f-..G). Manufacturers Agro Life Science; Fertiagro; Krishi Rasayan; Krishi Rasayan Exports Pvt.
`U.'.td.; Suzhou Hengtai; Syngenta Patents US 4664696.
`
`*PPLICATIONS: Site of action Sterol demethylation inhibitor.
`Spectrum and route of action Systemic fungicide with protective, curative, and eradicant action.
`
`cyproconazole
`
`277
`
`

`

`Absorbed rapidly by the plant, with translocation acropetally. Uses Foliar, systemic fungicide f:r,
`control of Septoria, rust, powdery mildew, Rhynchosporium, Cercospora and Ramularia in cereals ari·"·
`sugar beet, at 60-100 g/ha; and rust, Mycena, sclerotinia and Rhizoctonio in coffee and turf.
`. ;}
`Formulation types EC; WG; SL; SC Selected products Akenaton (Rocca); Alto (Syngenta); }
`Caddy (Bayer CropScience) Selected mixtures Aproach Prima (DuPont); Menara (Syngenta);)/'
`Sphere (Bayer CropScience)
`\
`
`ANALYSIS: Product analysis by rp hplc with uv detection (C/PAC Handbook, 2000, J, 29). . • ;ii
`
`Product analysis by glc or hplc. Residues determined by glc.
`· :\;
`TOXICOLOGICAL & ENVIRONMENTAL REVIEWS: JMPR Evaln. 1120 (2010); EU Rev. R;/
`SANC0/10344/2011 (2011); EFSAJou. 2010, 8(11), 1897 [73 pp.].
`EU status (1107/2009) Approved Legislation 2011/56/EU, (EU) 540/2011
`MAMMALIAN TOXICOLOGY: Acute oral (LD50, mg/kg) male rats 350, female rats 1333\m
`male mice 200, female mice 218 Acflte percutaneous (LD50, mg/kg) rabbits >2000, rats
`.\\
`i/i
`> 2000 Skin irritation Not an irritant (guinea pigs, rabbits). Skin sensitisation Not a
`Inhalation (LCso, mg/I) rats >5.65 (4 hJ/:
`sensitiser (guinea pigs). Eye Not an irritant (rabbits).
`\ii:
`NOEL (1 y) for dogs 3.2 mg/kg b.w. daily; (2 y) for rats 2 mg/kg b.w. daily. ADI/RID (BfR)
`\t
`0.01 mg/kg b.w. [2002]; (company proposed value, EC DAR) 0.02 mg/kg b.w. [2006]; (EPA)
`0.01 mg/kg b.w. [1993]. Toxicity class: WHO (a.I.) II EC classification (R63/ Xn; R22I N; .··.···
`RSO, R53) Other Not mutagenic in the Ames assay.
`. ....
`d.,
`ECOTOXICOLOGY: Birds Acute oral LD50 for bobwhite quail 131 mg/kg (geomean of 2
`tests). Dietary LC50 (5 d) for bobwhite quail 856 (geomean of 2 tests), maUard ducks 851 mg/kg}\
`diet. Fish LC50 (96 h) for carp 20, trout 19, bluegill sunfish 21 mg/L Daphnia LC50 (48 h)
`·
`> 26 mg/I. Algae EC50 (96 h) for Scenedesmus subspicotus 0.077 mg/L
`Bees (LD50, mg/bee) >100 (contact) (24 h); >1000 (oral) (24 h) Worms LC50 (14 d)
`335 mg/kg dry soil.
`
`ENVIRONMENTAL FATE: Animals In mammals, following oral administration, cyproconazot~'>
`:/i>
`is rapidly absorbed, extensively metabolised and excreted, DT50 c. 30 h. No bioaccumutation.
`Plants In different crops, metabolic pathways are similar and the major residue is cyproconazole:)
`itself. Soil/Environment ln soil, cyproconazole degrades moderately quickly, DT 50 c. 4 mo. (lab}'
`n = 8), c. 40 d (fie{d, n = 37). No accumulation and leaching potential. Soil adsorption Freundlich;
`K00 364 ml/g. Hydrolytically and photolytkally stable. In aquatic systems (n = 2) DT 50 5.6 d
`(water), > 1 y (whole system).
`
`201
`
`cyprodinil
`
`FRAC 9, D1
`
`anilinopyrimidine
`
`Fungici
`
`~NHYN~
`V
`
`N~
`CH3
`
`NOMENCLATURE: Common name cyprodinil (BSl, E-ISO, (m) F-1S0)
`IUPAC name 4-cyclopropyl-6-methyl-N-phenylpyrimidin-2-amine
`
`278
`
`cyprodinil
`
`

`

`MAMMALIAN TOXICOLOGY: Acute oral (LD 50, mg/kg) male rats 36, female rats 24, male
`mice 94.8, female mice 59.4 Acute percutaneous (LD50, mg/kg) male rats 2850, female rats
`538 NOEL (104 w) for rats 0.73 mg/kg daily. ADI/RfD (EPA) cRfD 0.00001 mg/kg b.w. [1991].
`Toxicity class: WHO (a.I.) la EC classification T +; R27/281 N; RS0, R53 Other Causes
`delayed neurotoxicity in hens,
`
`ECOTOXICOLOGY: Birds Acute oral LD50 for ring-necked pheasants >165, bobwhite qua