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CLOTHIANIDIN (238) First Draft Prepared by T Van Der Velde-Koerts, PH Van Hoeven-Arentzen and CM Mahieu,Centre for Substances An

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CLOTHIANIDIN (238) First Draft Prepared by T Van Der Velde-Koerts, PH Van Hoeven-Arentzen and CM Mahieu,Centre for Substances An Chlothianidin 495 CLOTHIANIDIN (238) First draft prepared by T van der Velde-Koerts, PH van Hoeven-Arentzen and CM Mahieu,Centre for Substances and Integrated Risk Assessment, National Institute of Public Health and the Environment (RIVM), the Netherlands EXPLANATION Residue and analytical aspects of clothianidin were considered for the first time by the present Meeting. The residue evaluation was scheduled for the 2010 JMPR by the Forty-first Session of the 2009 CCPR (ALINORM 09/32/24). Clothianidin is a soil, foliar and seed insecticide belonging to the chemical class of nitromethylenes or neonicotinoids and acts as an agonist of the nicotinic acetylcholine receptor, affecting the synapses in the insect central nervous system of sucking and chewing insects. It has registered uses in many countries on fruits, vegetables, soya beans, cereals, sugar cane, oilseeds and tea. The manufacturer supplied information on identity, metabolism, storage stability, residue analysis, use patterns, residues (resulting from supervised trials on pomefruit, stonefruit, cranberries, grapes, persimmons, bananas, head cabbage, broccoli, fruiting vegetables, lettuce, soya beans, carrots, potatoes, sugarbeets, chicory roots, cereals, sugar cane and oilseeds), and fates of residues during processing, and livestock feeding studies. In addition, Australia, The Netherlands and Japan supplied information on use patterns. IDENTITY ISO common name: Clothianidin Chemical name IUPAC: (E)-1-(2-chloro-1,3-thiazol-5-ylmethyl)-3-methyl-2- nitroguanidine CAS: [C(E)]-N-[(2-chloro-5-thiazolyl)methyl]-N'-methyl-N''- nitroguanidine CAS Registry No: 210880-92-5 CIPAC No: 738 Synonyms and trade names: TI-435, TM-444, V-10170 Structural formula: H NO2 N N CH Cl 3 S NH N CH2 Molecular formula: C6H8ClN5O2S Molecular weight: 249.68 496 Chlothianidin Clothianidin exists predominantly in the E-form. This has been confirmed by NMR analysis (Jeschke et al., 2003). Quantum chemical calculations revealed that in water the E-isomer is more stable than the Z-isomer. At room temperature the theoretical ratio between E/Z isomers is estimated as 65:1 (Schindler, 2010). PHYSICAL AND CHEMICAL PROPERTIES Pure active ingredient, minimum purity 99.7% Parameter Result References Guidelines/method Appearance purity 99.7%, 21.0–21.5 °C (Kamiya and Itoh, visual inspection; odourless, clear and colourless solid (powder) 2000a/c/e, THP-0009, THP- olfactory 0011, THP-0016) observation Vapour pressure purity 99.7% (Morrisey and Kramer, EEC A4 (effusion 1.3 × 10-7 mPa at 25 °C 2000b, THP-0026) method: vapour 3.8 × 10-8 mPa at 20 °C (extrapolated) pressure balance) Melting point purity 99.7% (Kamiya and Itoh, 2000g, OECD 102 (method 176.8 °C THP-0018) not indicated) the measured melting point was corrected taking into account the reference melting point of 2 standards Octanol/water Study 1, purity 99.7% (Morrisey and Kramer, OECD 117 (HPLC- partition log Kow = 0.7, unbuffered, pH not stated, at 2000a, THP-0013) method) coefficient 25.0 °C eluting solvent = water/MeOH 60/40 Study 2, purity 99.7% (O’Connor and Mullee, EEC A8 (shake log Kow = 0.893, pH 4, at 25 °C 2001, THP-0065) flask log Kow = 0.905, pH 7, at 25 °C method + HPLC- log Kow = 0.873, pH 10, at 25 °C UV) Solubility Study 1, purity 99.7% (Morrisey and Kramer, OECD 105 (flask 0.327 g/L in water at 20 °C 2000a, THP-0013) method + HPLC- UV) Study 2, purity 99.7% (O’Connor and Mullee, OECD 105 (flask 0.304 g/L in pH 4 buffer (0.01 M potassium 2001, THP-0065) method + HPLC- hydrogen phtalate) at 20 °C UV) 0.340 g/L in pH 10 buffer (0.002 M disodium tetraborate/0.004 M sodium chloride) at 20 °C Study 3, purity 99.7% (Morrisey and Kramer, OECD 105 (flask < 0.00104 g/L in heptane at 25 °C 2000a, THP-0013) method + HPLC- 0.0128 g/L in xylene at 25 °C UV) 1.32 g/L in DCM at 25 °C 6.26 g/L in MeOH at 25 °C 0.938 g/L in octanol at 25 °C 15.2 g/L in acetone at 25 °C 2.03 g/L in ethylacetate at 25 °C Relative density purity 99.7% (Morrisey and Kramer, OECD 109 20 D4 = 1.61 2000a, THP-0013) (pycnometer (kerosene was used as immersion solvent) method) Hydrolysis in [thiazolyl-14C]-labelled ai, chemical purity (Lewis, 2000, THP-0024) EEC C7 water > 98%, radiochemical purity > 99%, 0.3 mg/L in aqueous buffer with 0.7% v/v ACN under sterile conditions in the dark for 33 days. Preliminary tests at 50 °C: at pH 4 and 7: hydrolytic stability (< 10% hydrolysis in 5 d) at pH 9: DT50 = 14.4 d Definitive tests at pH 9: at 74 °C: DT50 = 0.68 d at 62 °C: DT50 = 3.7 d at 20 °C: DT50 = 1401 d (calculated using Arrhenius equation) Chlothianidin 497 Parameter Result References Guidelines/method Hydrolysis products (identified at pH 9 at 74 °C) max 59% ACT (2-chlorothiazol-5- ylmethylamine) max 23% TZMU (N-(2-chlorothiazol-5- ylmethyl)-N’-methylurea) max 5% CTNU (N-(2-chlorothiazol-5- ylmethyl)-N’-nitrourea) Photolysis in water [nitroimino-14C]- and [thiazolyl-2-14C]-labelled (Babczinski and Bornatsch, SETAC-procedures ai, radiochemical purity > 99%: as 0.284– 2000, THM-0013) (xenon light with 0.305 mg/L in phosphate buffer pH 7 (sterile (Schad, 2000a, THM-0016) UV filter, cut off λ conditions, cosolvent ACN < 1% v/v), < 290 nm) continuous irradiation for 18 d using xenon light Photolysis rate: DT50 = 3.3 hr (mean of 2 labels) at 25 °C Major photolysis products: TZMU: N-(2-chlorothiazol-5-ylmethyl)-N’- methylurea (18.7-27.5% after 18 d) MG: methylguanidine (34.7% after 18 d) HMIO: 4-hydroxy-2-methylamino-2- imidazolin-5-one (7.1% after 18 d) FA: formamide (14.1% after 18 d) MU: methylurea (11.0% after 18 d) CO2 (34.1% after 18 d in thiazolyl study) Dissociation purity 99.7% (Morrisey and Kramer, OECD 112 constant: at 20 °C: pKa = 11.09 2000a, THP-0013) (spectrophotometric dissociated species of clothianidin estimated to method) be the deprotonated compounds at the guanidine moiety Technical material, minimum purity 97.6% Parameter Result References Guidelines Appearance: purity 97.6%, 24.5–25.0 °C (Kamiya and Itoh, visual inspection; odourless, dim yellow solid (powder) 2000b/d/f, THP-0010, THP- olfactory 0012, THP-0017) observation Relative density: purity 97.6% (Kramer and Telleen, 2000, CIPAC MT 3 20 D4 = 1.59 THP-0014) (pycnometer (kerosene was used as immersion solvent) method) Melting range: no data submitted – – Stability study 1, purity 97.6% (Kramer and Telleen, 2000, Visual assessment Test substance is stable for 14 days at 54 ± THP-0014) + weighing + 2 °C and at 25 ± 2 °C. determination a.s. Test substance is stable for 14 days at 25 ± content (HPLC- 2 °C when placed in contact with zinc, iron and UV) aluminum metals or ions. Test substance is stable for 24 hrs at 25 ± 2 °C when exposed to light from a xenon arc lamp FORMULATIONS Clothianidin has been evaluated by JMPS in 2010. FAO specifications are available for clothianidin technical material, aqueous suspension concentrate, water soluble granules and granules. Clothianidin is available in many different types of formulations: water dispersible granules (WG 500 g/kg, also referred to as WDG), water soluble granules (SG 160 g/L, also referred to as WSG), water soluble powders (SP 160 g/L), suspension concentrates (SC 80, 200, 255 or 600 g/L, also referred to as flowable concentrate FL), granules (GR 5 g/kg), dustable powder (DP 1.5 or 498 Chlothianidin 5 g/kg) and flowable concentrate for seed treatment (FS 10, 100, 120, 180, 250, 285.7, 333.3, 400, 600 g/kg or 453 g/kg in combination with beta-cyfluthrin, also referred to as ST). Table 1 List of reference compounds used in various study reports Abbreviation Chemical structure Trivial and systematic chemical names Found as or in Other abbreviations used in study reports TI-435 N clothianidin (parent compound) rat, goat, hen; H H N N Syngenta code CGA 322704 (thiametoxam maize, sugarbeet, CH Cl S 3 evaluation) apple, tomato; N soil, water, NO2 rotational crops TZNG N thiazolylnitroguanidine; rat, goat, hen; H desmethyl-TI-435; maize, sugarbeet, NH N 2 N-(2-Chlorothiazol-5-ylmethyl)-N’- apple, tomato Cl S nitroguanidine soil; N Syngenta code CGA 265307 (thiametoxam rotational crops NO2 evaluation) or N Cl NH NH S NO2 NH TZMU N thiazolylmethylurea; rat, goat; H H N N N-(2-Chlorothiazol-5-ylmethyl)-N’- maize, sugarbeet; CH Cl S 3 methylurea apple; O Syngenta code CGA 353968 (thiametoxam soil, water; evaluation) rotational crops not found in tomato nor in hen TZG N thiazolylguanidine rat, goat, hen; H 2-Chlorothiazol-5-ylmethyl guanidine not found in N NH2 Syngenta code NOA 421276 (thiametoxam maize Cl S evaluation) NH TZU N thiazolylurea; rat, goat, hen; H NH TI-435 urea maize, sugarbeet; N 2 2-Chlorothiazol-5-ylmethyl urea apple; Cl S Syngenta code Metab 4U, Metab 8 U or rotational crops O Metab 13U (thiametoxam evaluation) not found in tomato, soil TMG N thiazolylmethylguanidine rat, goat, hen; H H N N N-(2-Chlorothiazol-5-ylmethyl)-N’- maize; sugarbeet, CH Cl S 3 methylguanidine apple; NH Syngenta code NOA 421275 (thiametoxam rotational crops evaluation) not found in tomato, soil, water TMHG N N-2-Chlorothiazol-5-ylmethyl-N’-hydroxy- goat; H H N N N’’-methyl-guanidine not found in CH maize nor in hen Cl S 3 N OH TMT N 3-(2-Chlorothiazol-5-yl)methylamino-5- hen H N N methyl-1H-1,2,4-triazole CH3 Cl S N NH THMN N OH N-hydroxy parent compound; rat, H N N N-2-Chlorothiazol-5-ylmethyl-N-hydroxy- apple CH Cl S 3 N’-methyl-N’’-nitroguanidine N NO2 Chlothianidin 499 Abbreviation Chemical structure Trivial and systematic chemical names Found as or in Other abbreviations used in study reports THMN-glc HO O-ß-D-Glucopyranosyl-THMN apple HO O HO O OH N H N N CH
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