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459 Thyroid 0.050 0.055 17.975 Skin 0.029 0.014 8.745 Carcass 0.017 0.009 6.540 From Printz & Bornatsch (1997) 14 C-thiazolidine-labelled thiacloprid was found to be rapidly and extensively absorbed in rats. No significant differences in the extent or route of excretion were noted between dose groups or sexes. Findings in the male group at the highest dose were consistent with delayed absorption (Printz & Bornatsch, 1997). Plasma concentrations of radioactivity were comparable for 14 C-thiazolidine- and 14 C-methylenelabelled thiacloprid. The Cl values were slightly greater for [ 14 C-methylene]thiacloprid, while the AUC values were markedly greater for [ 14 C-thiazolidine]thiacloprid. The AUC value for [ 14 C-thiazolidine] thiacloprid was approximately 170 times greater than the value obtained for [ 14 C-methylene]thiacloprid at 100 mg/kg bw. However, the AUC estimated for the 14 C-thiazolidine-labelled thiacloprid at 100 mg/kg bw was considered to be unreliable due an unsatisfactory mathematical description of the plasma curve with the model used. Excretion of radioactivity in urine was slightly greater and consequently lower in faeces for 14 C-thiazolidine labelled thiacloprid. Residues of 14 C-thiazolidine-labelled thiacloprid were found to be higher than residues of 14 C-methylene-labelled thiacloprid. 1.2 Biotransformation (a) 14 C-methylene-labelled thiacloprid In a study of biotransformation, groups of five male and five female Wistar rats received 14 C-methylene-labelled thiacloprid (purity of unlabelled test substance, 99.6%; radiochemical purity, > 99%) as a single dose at 1 or 100 mg/kg bw in 0.5% tragacanth orally by gavage, or intravenously as a single dose at 1 mg/kg bw. An additional group received unlabelled thiacloprid as 14 consecutive oral doses at 1 mg/kg bw per day followed by radiolabelled thiacloprid as a single oral dose at 1 mg/kg bw. Faecal and urine samples analysed were collected and metabolites were identified by high-performance liquid chromatography (HPLC), gas chromatography-mass spectrometry (GC-MS), liquid chromatography-mass spectrometry (LC-MS) and proton nuclear magnetic resonance ( 1 H-NMR). A total of 14 metabolites were identified, accounting for 57.8–78.7% of the administered radioactivity (Table 8). Small amounts (0.9–6.4%) of unchanged parent compound were also identified. With the exception of females at the highest dose, the major metabolite in all groups was identified as M07 (11.5–34.2%). The major metabolite in females at the highest dose was found to be (M12 + M13), accounting for 13.2% of the administered radioactivity. The major faecal metabolites were found to be M01 and unchanged parent compound. The amount of M11 was found to be significantly higher in males at the highest dose (13.4%) than in females at the highest dose (1.4%). Both M11 and M16 were found in higher amounts in male excreta while M06 and M07 were found in higher amounts in females. The main metabolic transformation was the oxidative cleavage of the parent molecule to yield 6-chloronicotinic acid (M03) which then reacted with glycine to form a hippuric acid type conjugate (M07). Other metabolic reactions included oxidation of the N-nitrile group to form amide derivatives (M11 and M17), opening of the thiazolidine ring by oxidation to give sulfoxide compounds (M08 and M10) and the replacement of the chlorine atom attached to the pyridine ring of chloronicotinic acid by mercaptoacetic acid (M06). In the groups receiving the highest dose, the concentrations THIACLOPRID X-X JMPR 2006
460 of unchanged parent compound were increased while the concentrations of M07 decreased. This suggested that the metabolic rate was reduced at the highest dose (Klein & Bornatsch, 1998). Table 8. Quantification of metabolites in the urine and faeces of rats 48 h after dosing with 14 C-methylene-labelled thiacloprid Metabolite Quantity of metabolite (% of recovered radioactivity) 1 mg/kg bw (iv) 1 mg/kg bw 1 mg/kg bw 100 mg/kg bw (repeated doses) Males Females Males Females Males Females Males Females Urine Thiacloprid 3.4 3.3 2.5 2.8 1.8 1.9 4.5 5.9 M01 (WAK 6856) 2.6 3.9 2.8 3.8 2.4 3.9 2.8 4.7 M03 (6-CNA) 6.8 9.7 7.1 8.7 8.0 9.1 9.0 4.2 M06 (KNO1886) 1.6 2.8 1.7 2.8 1.7 2.3 1.2 3.5 M07 (WAK 3583) 34.2 27.1 33.4 31.5 30.3 27.2 15.6 11.5 M08 (KNO 2672) 1.2 2.2 0.8 1.5 1.1 1.5 1.9 1.2 M09 (KNO1889) 2.4 6.1 3.3 5.1 3.6 5.6 1.4 1.1 M10 (KNO 1891) 1.4 1.2 1.4 1.7 1.2 0.9 ND 1.6 M11 (KNO 1893) 5.4 ND 3.6 ND 5.8 1.0 12.4 1.1 M12 (KNO 2621) + M13 1.2 1.4 0.9 1.6 0.9 1.5 2.2 13.0 (KNO 2665) M14 (KNO 1872) 1.2 1.2 1.1 1.1 1.3 0.9 2.7 2.1 M15 (KNO 2684) ND 0.5 ND 0.4 0.3 ND 0.8 1.7 M16 (NTN 35078) 2.9 1.3 2.8 1.1 2.4 0.6 4.0 1.1 M17 (KNO 1864) 1.0 0.7 0.7 0.8 0.7 0.4 0.4 0.6 Sum of metabolites in urine 65.4 61.3 62.1 62.8 61.6 56.9 59.1 53.2 Faeces Thiacloprid 2.9 2.6 2.1 1.5 2.0 1.8 6.4 0.9 M01 (WAK 6856) 3.2 1.6 2.8 1.4 3.1 1.9 5.8 1.4 M06 (KNO1886) 1.2 1.5 1.4 1.8 1.5 2.2 1.2 0.4 M08 (KNO 2672) 1.3 1.5 1.4 1.0 1.2 1.2 1.3 0.4 M09 (KNO1889) 0.3 0.7 0.6 0.4 0.5 0.4 0.3 0.2 M10 (KNO 1891) 0.4 ND ND ND ND 0.4 ND ND M11 (KNO 1893) 1.2 0.5 1.1 0.7 1.0 0.8 1.0 0.3 M12 (KNO 2621) + M13 0.7 0.6 0.6 0.5 0.4 0.4 0.9 0.2 (KNO 2665) M14 (KNO 1872) 0.4 0.7 0.6 0.4 0.5 0.5 0.7 0.2 M15 (KNO 2684) ND 0.5 ND ND ND 0.9 0.3 0.2 M16 (NTN 35078) 0.8 0.3 1.0 0.3 0.8 1.0 1.2 0.2 M17 (KNO 1864) 0.3 0.2 0.2 0.2 0.3 0.3 0.4 0.1 Sum of metabolites in faeces 12.7 10.6 11.8 8.3 11.2 11.9 19.5 4.4 Total (urine + faeces) 78.0 72.0 74.0 71.2 72.6 68.8 78.7 57.8 From Klein & Bornatsch (1998) iv, intravenous; ND, not detected. THIACLOPRID X-X JMPR 2006
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Pesticide residues in food — 2006
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TABLE OF CONTENTS Page List of part
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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
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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
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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
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113 Rat Groups of 20 male and 20 fe
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115 group and in the groups at the
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117 cyfluthrin (purity, 95.5-95.9%)
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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
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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
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143 The Meeting concluded that the
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145 Estimate of acute reference dos
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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
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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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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
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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
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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
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212 for which the LD 50 was > 2000
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214 substances. Since conventional
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216 Critical end-points relevant fo
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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
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224 Toxicology Laboratory (Tunstall
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226 Ullrich, B. (2003) Report on a
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228 Cyromazine was first evaluated
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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.
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236 Because of the low total recove
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238 Name Description Compound found
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240 After each dose of [U- 14 C tri
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242 In male and female monkeys give
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244 stress and discomfort during th
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246 Table 18. Dermal absorption of
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248 rate under steady-state conditi
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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
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258 Analysis of the diets showed th
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260 considered to be biologically s
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262 observed incidence probably rel
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264 c Cyromazine was assayed twice
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266 2.5 Reproductive toxicity (a) M
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268 either sporadic or as a consequ
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270 fetuses were removed, weighed a
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272 The NOAEL for maternal toxicity
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274 In New Zealand White rabbits, c
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276 and litters with malformations.
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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
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288 Other toxicological studies Tox
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290 IARC (1999a) Some chemicals tha
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292 Simoneaux, B. & Marco, G. (1984
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294 Declaration of Helsinki (Cristi
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296 lowered arousal level at doses
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298 Cerebellum 3 1 51** 76** 80** 7
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300 Table 4. Maximum inhibition of
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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
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312 Human a Dietary administration
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314 Piccirillo, V.J. (1978) Acute o
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316 Haloxyfop (racemic), its sodium
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318 Recovery of radioactivity in ur
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320 skin of nine male and nine fema
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322 1.2 Biotransformation Mice In a
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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
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332 All dogs were killed for autops
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334 with that of controls (but no s
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336 Table 4. Results of studies of
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338 doses of up to 1.0 mg/kg bw per
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340 delayed ossification in the hyo
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342 Mice In a GLP-compliant study,
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344 and in females at the highest d
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346 Between January 1999 and Januar
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348 The Meeting concluded that halo
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350 Critical end-points for setting
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352 Elcombe, B.M. (2002a) Effects o
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354 Scortichini, B.H., Bohl, R.W. &
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356 Economic Co-operation and Devel
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358 There were no treatment-related
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360 comparable to control levels. A
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362 Groups of 17 male and 17 female
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364 No compound-related effects wer
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366 Berry, D. & Gore, C.W. (1975) P
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368 Quinoxyfen has not been evaluat
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370 In the main study, which compli
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372 Concentrations of total radioac
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374 several hydroxy-quinoxyfen meta
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376 There were no mortalities or ad
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378 at doses of ≥ 100 mg/kg bw pe
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380 In a GLP-compliant study to det
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382 control group. This was observe
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384 The homogeneity and stability o
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386 Testes weight (g) at 24 months
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388 slight (3 out of 30) hepatocell
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390 marked inanition, decreased fae
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392 Females Relative liver weightt
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394 were patch-tested specifically
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396 In studies of developmental tox
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398 Rat, LC 50 , inhalation Rabbit,
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400 Gollapudi, B.B. & Lick, S.J. (1
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TEMEPHOS First draft prepared by De
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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: 458 Table 6. Excretion of radioacti
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: 494 2.5 Reproductive toxicity (a) M
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
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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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