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399 References Baker, P.C. & Yano, B.L. (2000). Quinoxyfen: 4-week dermal toxicity study in Fischer 344 rats. Dow AgroSciences, Unpublished report No. DECO HET DR-0325-7474-068, dated 14 September 2000. Submitted to WHO by Dow AgroSciences, Indianapolis, USA. Beekman, M.J. (1994) XDE-795: acute aerosol inhalation toxicity study with Fischer 344 rats. Unpublished report No. DR-0235-7474-012 from Toxicology Research Laboratory, Dow Chemical Company, Michigan, USA. Submitted to WHO by Dow AgroSciences, Indianapolis, USA. Bellringer, M. (1995) XDE-795: potential tumorigenic effects in prolonged dietary administration to CD-1 mice. Unpublished report No. DWC 657/942900 from Huntingdon Research Centre Ltd, Huntingdon, England. Submitted to WHO by Dow AgroSciences, Indianapolis, USA. Brooker, A.J. (1994) XDE-795: a study of the effect on the pregnancy of the rat. Unpublished report No. DWC 660 & 658/931071 from Huntingdon Research Centre Ltd, Huntingdon, England. Submitted to WHO by Dow AgroSciences, Indianapolis, USA. Burns, P.J. (1995) Plant report 969 building, special reference: XDE-795 campaign. Submitted to WHO by Dow AgroSciences, Indianapolis, USA. Brzak, K.A. (2001). Quinoxyfen (DE-795): determination of hydroxylated metabolites of quinoxyfen following a repeated oral administration in Fischer 344 rats. Unpublished report No. DECO HET DR-0325-7474-073, dated 22 February 2001, from Dow AgroSciences. Submitted to WHO by Dow AgroSciences, Indianapolis, USA. Charles, I., Bass, S. & Brownson, P.J. (2006). Plant report Letcombe/Kings Lynn quinoxyfen manufacturing. Unpublished report dated 18 September 2006. Submitted to WHO by Dow AgroSciences, Indianapolis, USA. Cosse, P.F., Stebbins, K.E., Redmond, J.M. & Ormand, J.R. (1995) XDE-795: one year chronic dietary toxicity study in beagle dogs. Unpublished report No. DR-0325-7474-011 from Toxicology Research Laboratory, Dow Chemical Company, Michigan, USA. Submitted to WHO by Dow AgroSciences, Indianapolis, USA. Dunsire, J.P. & Paul, H.J. (1995) The disposition of [ 14 C]-XDE-795 in the lactating goat. Unpublished report No. 10043 from Inveresk Research International, Scotland. Submitted to WHO by Dow AgroSciences, Indianapolis, USA. Foulds, I.S. (1994) Report on Andrew Fowles. Unpublished report Nos ISF/PT/S160621 & ISF/PT/S1670621 from Birmingham City Hospital NHS Trust, England. Submitted to WHO by Dow AgroSciences, Indianapolis, USA. Gilbert, K.S. (1994a) XDE-795: acute oral toxicity study in Fischer 344 rats. Unpublished report No. DR- 0325-7474-010A from Toxicology Research Laboratory, Dow Chemical Company, Michigan, USA. Submitted to WHO by Dow AgroSciences, Indianapolis, USA. Gilbert, K.S. (1994b) XDE-795: acute dermal toxicity study in New Zealand White rabbits. Unpublished report No. DR-0325-7474-010D from Toxicology Research Laboratory, Dow Chemical Company, Michigan, USA. Submitted to WHO by Dow AgroSciences, Indianapolis, USA. Gilbert, K.S. (1994c) XDE-795: primary dermal irritation study in New Zealand White rabbits. Unpublished report No. DR-0325-7474-010B from Toxicology Research Laboratory, Dow Chemical Company, Michigan, USA. Submitted to WHO by Dow AgroSciences, Indianapolis, USA. Gilbert, K.S. (1994d) XDE-795: primary eye irritation study in New Zealand White rabbits. Unpublished report No. DR-0325-7474-010C from Toxicology Research Laboratory, Dow Chemical Company, Michigan, USA. Submitted to WHO by Dow AgroSciences, Indianapolis, USA. Gilbert, K.S. (1994e) XDE-795: dermal sensitisation potential in the Hartley albino guinea-pig. Unpublished report No. DR-0325-7474-010E from Toxicology Research Laboratory, Dow Chemical Company, Michigan, USA. Submitted to WHO by Dow AgroSciences, Indianapolis, USA. QUINOXYFEN X-X JMPR 2006
400 Gollapudi, B.B. & Lick, S.J. (1994) Evaluation of XDE-795 in the mouse bone marrow micronucleus test. Unpublished report No. DR-0325-7474-016 from Toxicology Research Laboratory, Dow Chemical Company, Michigan, USA. Submitted to WHO by Dow AgroSciences, Indianapolis, USA. Grandjean, M. & Szabo, J.R (1992) XR-795: 13-week dietary toxicity study in CD-1 mice. Unpublished report No. DR-0325-7474-003 from Toxicology Research Laboratory, Dow Chemical Company, Michigan, USA. Submitted to WHO by Dow AgroSciences, Indianapolis, USA. Johnson, I.R (1995) XDE-795 Technical: delayed contact hypersensitivity study in the guinea-pig. Unpublished report No. GHE-T-486 from Pharmaco-LSR, Eye, England. Submitted to WHO by Dow AgroSciences, Indianapolis, USA. Liberacki, A.B., Breslin, W.J., Zwicker, G.M., Johnson, K.A. & Freshour, N.L. (1995) XDE-795: two-generation dietary reproduction study in Sprague-Dawley rats. Unpublished report No. DR-0325-7474-013 from Toxicology Research Laboratory, Dow Chemical Company, Michigan, USA. Submitted to WHO by Dow AgroSciences, Indianapolis, USA. Linscombe, V.A. & Lick, S.J (1994) Evaluation of XDE-795 in an in vitro chromosomal aberration assay utilising rat lymphocytes. Unpublished report No. DR-0235-7474-018 from Toxicology Research Laboratory, Dow Chemical Company, Michigan, USA. Submitted to WHO by Dow AgroSciences, Indianapolis, USA. Merkel, D. J. (2004). 3-OH quinoxyfen metabolite: acute oral toxicity up and down procedure in rats. Unpublished report No. DECO HET DR-0362-5783-003, dated 18 September 2004, from Dow AgroSciences. Submitted to WHO by Dow AgroSciences, Indianapolis, USA. Pant, K.J. (1994) Test for chemical induction of gene mutation at the HGPRT locus in cultured Chinese hamster ovary (CHO) cells with and without metabolic activation. Unpublished report No. 0217-2510 from Sitek Research Laboratories, Rockville, USA. Submitted to WHO by Dow AgroSciences, Indianapolis, USA. Pearson, N.R. & Reeves, G.L. (2005). Determination of the correct structure for the major aerobic soil metabolite of quinoxyfen. Study SPS-04-007. Unpublished report No. PTR 11344088-6033-1, from Dow Agrosciences Laboratory, Indianapolis, USA. Submitted to WHO by Dow AgroSciences, Indianapolis, USA. Redmond, J.M., Quast, J.F., Bond, D.M. & Ormand, J.R. (1995) XDE-795: two year dietary chronic toxicity/ oncogenicity study in Fischer 344 rats - Final Report. Unpublished report No. DR-0325-7474-007 by Toxicology Research Laboratory, Dow Chemical Company, Michigan, USA. Submitted to WHO by Dow AgroSciences, Indianapolis, USA. Schumann, A.M., Dryzga, M.D., Pottenger, L.H., Stewart, H.S. &Bartels, M.J. (1995) XR-795: tissue distribution and metabolism of 14 C-labelled XDE-795 in Fischer 344 rats. Unpublished report No. DR 0325-7474-006 from Toxicology Research Laboratory, Dow Chemical Company, Michigan, USA. Submitted to WHO by Dow AgroSciences, Indianapolis, USA. Shankar, M.R. & Stebbins, K.E. (1999) Quinoxyfen: acute neurotoxicity study in Fischer 344 rats. Unpublished report No. DECO HET DR-0325-7474-045, Study No. 991068, from Toxicology and Environmental Research and Consulting, Dow Chemical Company, Michigan, USA. Submitted to WHO by Dow AgroSciences, Indianapolis, USA. Shankar, M.R., Stebbins, K.E. & Redmond, J.M. (1995) XDE-795: chronic neurotoxicity study in Fischer 344 rats. Unpublished report No. DR-0325-7474-007N from Toxicology Research Laboratory, Dow Chemical Company, Michigan, USA. Submitted to WHO by Dow AgroSciences, Indianapolis, USA. Szabo, J.R. & Davis, N.L (1992) XR-795: four week dietary toxicity study in Fischer 344 rats. Unpublished report No. DR-0235-7474-002 by Toxicology Research Laboratory, Dow Chemical Company, Michigan, USA. Submitted to WHO by Dow AgroSciences, Indianapolis, USA. Szabo, J.R. & Davis, N.L (1993) XR-795: four week dietary toxicity study in beagle dogs. Unpublished report No. DR-0325-7474-008 by Toxicology Research Laboratory, Dow Chemical Company, Michigan, USA. Submitted to WHO by Dow AgroSciences, Indianapolis, USA. QUINOXYFEN X-X JMPR 2006
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Pesticide residues in food — 2006
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TABLE OF CONTENTS Page List of part
Page 7 and 8:
Dr Helen Hakansson, Institute of En
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Abbreviations used ADI ALT APDM ARf
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Introduction The toxicological mono
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BIFENAZATE First draft prepared by
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5 In a series of experiments, group
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7 In a study of the time-course of
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9 the administered dose in males an
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11 limited absorption of parent com
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13 NAME/No. STRUCTURE D1989 OCH 3 D
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15 2.1 Acute toxicity Results of st
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17 (f) Sensitization In a study of
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19 Table 9. Clinical chemistry effe
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21 The degree of this finding was m
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23 On histopathological examination
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25 (equal to 0, 0.9, 10.4 or 25 mg/
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27 Haemoglobin (g/dl): Before treat
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29 weekly. Blood and urine samples
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31 (females) (equal to 0, 1.0, 3.9,
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33 Cytogenetic test Chinese hamster
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35 groups of 30 males and 30 female
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37 and placed in 10% ammonium sulfi
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39 was > 5000 mg/kg bw. The LC 50 i
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41 Multigeneration study of reprodu
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43 Medical data No significant adve
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45 Trutter, J.A. (1997a) 28-Day die
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48 Evaluation for acceptable daily
Page 63 and 64:
50 Table 2. Radioactivity in blood
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52 10 10 0.42 0.0462 0.63 0.0080 8.
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54 Figure 2. Transfer of radioactiv
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56 Skin 33.07 61.59 0.5 17.94 17.29
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58 Table 10. Summary of metabolites
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60 Table 14. Summary of identified
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62 Table 18. Summary of metabolites
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64 Table 19. Structures of identifi
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66 Metabolite Structure O M510F14 N
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68 Metabolite Structure M510F39 N O
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70 2. Toxicological studies 2.1 Acu
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72 1% Tylose CB 30.000. The injecti
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74 the end of dosing. Blood samples
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76 examinations were carried out 8
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78 concentrations were increased at
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80 times were slightly, but signifi
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82 in males and females rats at 250
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84 End-point Test object Dose a (LE
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86 parental rats was not markedly a
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88 groups in conception frequencies
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90 0.7 ± 3.5%, 1.8 ± 4.2%, 2.9 ±
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92 In this study of developmental n
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94 3. Observations in humans In the
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96 was 100 ppm, equal to 10 mg/kg b
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98 Acute toxicity Rat, LD 50 , oral
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100 Mellert, W., Kaufmann, W. & Hil
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CYFLUTHRIN AND BETA-CYFLUTHRIN Firs
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105 Table 1. Diastereoisomer pairs
Page 120 and 121:
107 (i) In vivo Rats Four groups of
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109 2. Toxicological studies 2.1 Ac
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111 Species Strain Sex Route Formul
Page 126 and 127:
113 Rat Groups of 20 male and 20 fe
Page 128 and 129:
115 group and in the groups at the
Page 130 and 131:
117 cyfluthrin (purity, 95.5-95.9%)
Page 132 and 133:
119 In a short-term study of exposu
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121 and dissection. At termination,
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123 2.5 Reproductive toxicity (a) M
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125 gestation. The vehicle was 1% C
Page 140 and 141:
127 females was exposed during days
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129 were not seen in rats in the co
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131 men was exposed for 1 h to actu
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133 40 g/l, in a flowable concentra
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135 were removed from five males an
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137 weights and food consumption we
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139 In females at the highest dose,
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141 The dermal toxicity of cyfluthr
Page 156 and 157:
143 The Meeting concluded that the
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145 Estimate of acute reference dos
Page 160 and 161:
147 Cage, S. (2004) [ 14 C]-beta-cy
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149 Heimann, K.G. (1984c) FCR 4545
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151 Jones, R.D. & Hastings, T.F. (1
Page 166 and 167:
153 Pauluhn, J. & Mohr, U. (1984).
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155 Von Keutz, E. (1987) FCR 4545 -
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158 Zeta-cypermethrin .............
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160 Evaluation for acceptable daily
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162 polar metabolites, which are fu
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164 for up to 70 days. Signs typica
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166 rapidly metabolized by cleavage
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Page 183 and 184:
170 Table 2. Effect of cis : trans
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172 Table 3. Significant haematolog
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174 Rabbits Occluded dermal applica
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176 1100 ppm in weeks 1-6, with inc
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178 Wistar-derived (Alderley Park)
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180 At 1500 ppm, liver APDM activit
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182 for premature deaths, 10 male a
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184 by gavage for days 7 to 19 of g
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186 observed at the intermediate an
Page 201 and 202:
188 The females recovered from this
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190 tibial nerve (SPTN), trigeminal
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194 for 5 weeks. Observations inclu
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196 caused obvious irritation and r
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198 days 6-15 of gestation. After m
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200 was observed in two males at 72
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202 control and other treated group
Page 217 and 218:
204 Table 14. Results of studies of
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206 (b) Developmental toxicity Rats
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208 mild and temporary paraesthesia
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210 range appeared to exist for the
Page 225 and 226:
212 for which the LD 50 was > 2000
Page 227 and 228:
214 substances. Since conventional
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216 Critical end-points relevant fo
Page 231 and 232:
218 Butterworth, S.T.G. & Clark, D.
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220 East Millstone, New Jersey, USA
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222 Jersey, USA. Submitted to WHO b
Page 237 and 238:
224 Toxicology Laboratory (Tunstall
Page 239 and 240:
226 Ullrich, B. (2003) Report on a
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228 Cyromazine was first evaluated
Page 243 and 244:
230 were taken for the measurement
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232 highest dose, rather than indic
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234 Tissue residues: Tissues a < 0.
Page 249 and 250:
236 Because of the low total recove
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238 Name Description Compound found
Page 253 and 254:
240 After each dose of [U- 14 C tri
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242 In male and female monkeys give
Page 257 and 258:
244 stress and discomfort during th
Page 259 and 260:
246 Table 18. Dermal absorption of
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248 rate under steady-state conditi
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Page 265 and 266:
252 the test substance. The method
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254 taken for haematological and bi
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256 not differ appreciably from pre
Page 271 and 272:
258 Analysis of the diets showed th
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260 considered to be biologically s
Page 275 and 276:
262 observed incidence probably rel
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264 c Cyromazine was assayed twice
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Page 281 and 282:
268 either sporadic or as a consequ
Page 283 and 284:
270 fetuses were removed, weighed a
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272 The NOAEL for maternal toxicity
Page 287 and 288:
274 In New Zealand White rabbits, c
Page 289 and 290:
276 and litters with malformations.
Page 291 and 292:
278 of melamine powder into the rab
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280 reduction in the survival of ma
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282 There is significantly less ris
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284 Toxicological data Cyromazine h
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286 Toxicological evaluation The Me
Page 301 and 302:
288 Other toxicological studies Tox
Page 303 and 304:
290 IARC (1999a) Some chemicals tha
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292 Simoneaux, B. & Marco, G. (1984
Page 307 and 308:
294 Declaration of Helsinki (Cristi
Page 309 and 310:
296 lowered arousal level at doses
Page 311 and 312:
298 Cerebellum 3 1 51** 76** 80** 7
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300 Table 4. Maximum inhibition of
Page 315 and 316:
302 auditory/physical examination w
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304 • • • • • Home-cage o
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306 Dogs Groups of four male and fo
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308 capsules. Some volunteers recei
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310 Blood was taken for measurement
Page 325 and 326:
312 Human a Dietary administration
Page 327 and 328:
314 Piccirillo, V.J. (1978) Acute o
Page 329 and 330:
316 Haloxyfop (racemic), its sodium
Page 331 and 332:
318 Recovery of radioactivity in ur
Page 333 and 334:
320 skin of nine male and nine fema
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322 1.2 Biotransformation Mice In a
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Page 339 and 340:
326 96%) at a concentration designe
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328 was centrilobular hepatocellula
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330 The treatment had no effect on
Page 345 and 346:
332 All dogs were killed for autops
Page 347 and 348:
334 with that of controls (but no s
Page 349 and 350:
336 Table 4. Results of studies of
Page 351 and 352:
338 doses of up to 1.0 mg/kg bw per
Page 353 and 354:
340 delayed ossification in the hyo
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342 Mice In a GLP-compliant study,
Page 357 and 358:
344 and in females at the highest d
Page 359 and 360:
346 Between January 1999 and Januar
Page 361 and 362: 348 The Meeting concluded that halo
Page 363 and 364: 350 Critical end-points for setting
Page 365 and 366: 352 Elcombe, B.M. (2002a) Effects o
Page 367 and 368: 354 Scortichini, B.H., Bohl, R.W. &
Page 369 and 370: 356 Economic Co-operation and Devel
Page 371 and 372: 358 There were no treatment-related
Page 373 and 374: 360 comparable to control levels. A
Page 375 and 376: 362 Groups of 17 male and 17 female
Page 377 and 378: 364 No compound-related effects wer
Page 379 and 380: 366 Berry, D. & Gore, C.W. (1975) P
Page 381 and 382: 368 Quinoxyfen has not been evaluat
Page 383 and 384: 370 In the main study, which compli
Page 385 and 386: 372 Concentrations of total radioac
Page 387 and 388: 374 several hydroxy-quinoxyfen meta
Page 389 and 390: 376 There were no mortalities or ad
Page 391 and 392: 378 at doses of ≥ 100 mg/kg bw pe
Page 393 and 394: 380 In a GLP-compliant study to det
Page 395 and 396: 382 control group. This was observe
Page 397 and 398: 384 The homogeneity and stability o
Page 399 and 400: 386 Testes weight (g) at 24 months
Page 401 and 402: 388 slight (3 out of 30) hepatocell
Page 403 and 404: 390 marked inanition, decreased fae
Page 405 and 406: 392 Females Relative liver weightt
Page 407 and 408: 394 were patch-tested specifically
Page 409 and 410: 396 In studies of developmental tox
Page 411: 398 Rat, LC 50 , inhalation Rabbit,
Page 416 and 417: TEMEPHOS First draft prepared by De
Page 418 and 419: 405 by thin-layer chromatography (T
Page 420 and 421: 407 In a special study to investiga
Page 422 and 423: 409 concluded that temephos was of
Page 424 and 425: 411 Table 3. Effects on mean erythr
Page 426 and 427: 413 Females 0 1.091 1.224 1.324 1.3
Page 428 and 429: 415 of up to 18 ppm. In the group a
Page 430 and 431: 417 Chromosomal aberration DNA repa
Page 432 and 433: 419 of the birds treated with temep
Page 434 and 435: 421 concentration of 1 ppm. Only on
Page 436 and 437: 423 being appreciably less than thi
Page 438 and 439: 425 Lowest relevant developmental N
Page 440: 427 WHO (1991) Safe use of pesticid
Page 443 and 444: 430 All new studies with thiabendaz
Page 445 and 446: 432 use of this dose form was consi
Page 447 and 448: 434 At 1000 mg/kg bw, qualitative e
Page 449 and 450: 436 At 100 mg/kg bw, slightly decre
Page 451 and 452: 438 There were no treatment-related
Page 453 and 454: 440 Table 6. Incidence of malformat
Page 455 and 456: 442 Dose (mg/kg bw) (grouped by exp
Page 457 and 458: 444 1157 12/21 (57.1)*** 27.2 ± 33
Page 459 and 460: 446 versus placebo): increased appe
Page 461 and 462: 448 activity, tiptoe gait, landing
Page 463 and 464:
450 Noakes, J.P. (2005a) Thianendaz
Page 465 and 466:
452 tests normally performed and th
Page 467 and 468:
454 Radiolabel was excreted primari
Page 469 and 470:
456 the excretory organs, was the r
Page 471 and 472:
458 Table 6. Excretion of radioacti
Page 473 and 474:
460 of unchanged parent compound we
Page 475 and 476:
462 M10 (KNO 1891) + M11 (KNO 1893)
Page 477 and 478:
464 on body weights. Exposure at 15
Page 479 and 480:
466 The no-observed-adverse-effect
Page 481 and 482:
468 Hepatocytes, hypertrophy 0 2 6
Page 483 and 484:
470 they may also be related to var
Page 485 and 486:
472 weights of males were approxima
Page 487 and 488:
474 Thyroid weight (mg): Week 12 6
Page 489 and 490:
476 Table 17. Relevant findings in
Page 491 and 492:
478 Dogs In a dose range-finding st
Page 493 and 494:
480 Prostate / uterine weight (g) 2
Page 495 and 496:
482 the treatment groups receiving
Page 497 and 498:
484 No gross findings were observed
Page 499 and 500:
486 received a macroscopic examinat
Page 501 and 502:
488 Although decreased concentratio
Page 503 and 504:
490 Sciatic nerve; No. examined 50
Page 505 and 506:
492 are caused by the higher incide
Page 507 and 508:
Page 509 and 510:
496 In a two-generation study of re
Page 511 and 512:
498 In dams that died or were sacri
Page 513 and 514:
500 No clinical signs or increased
Page 515 and 516:
502 Table 33. Selected variations a
Page 517 and 518:
504 Days 16-21 73.3 78.7 62.5 44.3*
Page 519 and 520:
506 Thiacloprid was not teratogenic
Page 521 and 522:
508 Table 37. Motor and locomotor a
Page 523 and 524:
510 Day 91 19.78 20.00 19.58 18.22*
Page 525 and 526:
512 Table 40. Selected findings in
Page 527 and 528:
514 plate incorporation procedure,
Page 529 and 530:
516 (iv) Comparative study on liver
Page 531 and 532:
518 and relative liver weight in an
Page 533 and 534:
520 at 2500 ppm. The administration
Page 535 and 536:
522 No macroscopic changes were det
Page 537 and 538:
524 The following procedures were p
Page 539 and 540:
526 litter for the group at 1000 pp
Page 541 and 542:
528 Hepatic enzyme activities in th
Page 543 and 544:
530 subtypes 1A1, 2B1, 2D1 and othe
Page 545 and 546:
532 Long-term studies of toxicity a
Page 547 and 548:
534 The Meeting concluded that ther
Page 549 and 550:
536 Estimate of acceptable daily in
Page 551 and 552:
538 dated 27 July, from Bayer AG, W
Page 553 and 554:
540 Kroetlinger, F. (1995a) YRC 289
Page 555 and 556:
542 Wetzig, H. & Geiss, V. (1998b)
Page 557 and 558:
544 Table A1. NOAELs and LOAELs for
Page 559 and 560:
546 2.2 Postulated mode of action (
Page 561 and 562:
548 • • • Chromosomal aberrat
Page 563 and 564:
550 Table A3. NOAELs and LOAELs for
Page 565 and 566:
552 Appendix 2 Table B1. List of an
Page 567 and 568:
554 Metabolite Structure / trivial
Page 569 and 570:
556 Metabolite Structure / trivial
Page 571 and 572:
558 Evaluation for acute reference
Page 573 and 574:
560 increased thyroid weights in th
Page 575 and 576:
562 Table 4. Results of bone-marrow
Page 577 and 578:
564 malformations between the contr
Page 579 and 580:
566 In a study of prenatal developm
Page 581 and 582:
568 combination of heparin and an a
Page 583 and 584:
570 Table 10. Selected findings fro
Page 585 and 586:
572 In a short-term study of neurot
Page 588 and 589:
ANNEX 1 Reports and other documents
Page 590 and 591:
577 31. Pesticide residues in food:
Page 592 and 593:
579 66. Pesticide residues in food
Page 594:
581 100. Pesticide residues in food
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