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DELTAMETHRIN (135) First Draft Prepared by Dugald Maclachlan, Department of Agriculture, Forestry and Fisheries, Australia

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DELTAMETHRIN (135) First Draft Prepared by Dugald Maclachlan, Department of Agriculture, Forestry and Fisheries, Australia 167 DELTAMETHRIN (135) First draft prepared by Dugald MacLachlan, Department of Agriculture, Forestry and Fisheries, Australia EXPLANATION Deltamethrin has been evaluated several times since the initial evaluation in 1980. It was last evaluated in 1992 for residues and in 2000 for toxicology. At the 30th Session of the CCPR, the Committee noted that deltamethrin was on the agenda of the 52nd JECFA (1999). At the 31st Session of the CCPR, the committee noted the MRLs estimated by JECFA for veterinary uses would be circulated for comments at step 3, through CL-RVDF, governments were invited to co-ordinate their comments at the national level. Deltamethrin was identified as a priority compound under the Periodic Re-evaluation Program at the 29th Session of the CCPR and scheduled for the 2002 JMPR. Data to support the existing CXLs and other critical data required for the estimation of MRLs have been provided by the company. The governments of Australia, The Netherlands, Poland and Germany have submitted information on national GAP and/or residue data. IDENTITY ISO Common name: deltamethrin Chemical name: IUPAC: (S)-α-cyano-3-phenoxybenzyl (1R,3R)-3-(2,2-dibromovinyl)-2,2- dimethylcyclopropanecarboxylate CA: [1R-[1α(S*),3α]]-cyano(3-phenoxyphenyl)methyl 3-(2,2-dibromoethenyl)-2,2- dimethylcyclopropanecarboxylate CAS No.: [52918-63-5] CIPAC No.: 333 Synonyms/trade names: decamethrin, AE F032640, RU 22974, HOE 032640, NRDC 161, FMC 45498 Structural formula: O Br C CH CO CN Br C O H HH CH CH 3 3 Molecular formula: C22H19Br2NO3 Molecular weight: 505.2 168 deltamethrin Physical and chemical properties Pure active ingredient Appearance: off-white solid powder (technical grade) (Thomas and Sweetapple, 1990) Melting point: 100-102°C (373-375°K), (technical grade) (Sweetapple, 1990) Partition coefficient, log Pow: 4.6 at 25ºC, pH 7,6 (not pH dependent) (Yoder, 1991a) Hydrolysis: pH 5 (buffered): negligible (Smith, 1990a) pH 7 (buffered): negligible (Smith, 1990a) pH 9 (buffered): half-life 2.5 days (mean value) (Smith, 1990a) pH 8 (buffered): half-life 31 days (Maurer and Schäfer, 2002) Photolysis: half-life 48 days. Quantum yield in wavelength range 290-385 nm was calculated to be 8.72 × 10-4 (C008524) Dissociation constant: deltamethrin is neither acid nor alkaline and dissociation is not expected to occur at environmentally relevant pH Technical material Minimum purity: 980 g/kg (technical grade) Vapour pressure: 1.24 × 10-8 Pa at 25ºC 4.13 × 10-8 Pa at 35ºC 1.98 × 10-7 Pa at 45ºC (Yoder, 1991b) Volatility: Henry’s law constant: 3.1 × 10-2 Pa.m3/mol based on a water solubility of 0.2 µg as/l and a vapour pressure of 1.24 × 10-8, both at 25ºC (A70747) (Grelet, 1995) Appearance: off-white solid powder (technical grade) Odour: odourless Density: 0.550 g/cm3 Table 1. Solubility of deltamethrin. Solvent Solubility Water: 0.2 µg/l at 25ºC (A26313, C009221) (Jamet and Hascoet, 1977; Mühlberger and Jordan, 2000a) Organic Solvents: Results measured at 20° C (A45109, C009220) (Yoder 1990, Mühlberger and Jordan 2000b) Cyclohexane 1-10% benzene and toluene 10-50% Xylenes 18 g/100ml at 25ºC 1,1,1-trichloroethane 10-50% iso-propanol <1% Ethanol 1-10% n-octanol 0.526 g/100ml at 25ºC Glycerol <1% Acetone 10-50% deltamethrin 169 Solvent Solubility Cyclohexanone >50% ethyl acetate 10-50% Thermal stability: stable to 270°C (Sanders, 1991) Flammability: not flammable or auto-flammable (Hoffmann, 1996a,b) Oxidizing potential: not oxidizing (Smeykal, 2000) Explosivity: not explosive (Smeykal, 2000) Formulations The following Table includes the major formulations developed for deltamethrin crop and animal health uses around the world. Table 2. Deltamethrin formulations and codes. Type Code number Concentration Agriculture Emulsifiable concentrate (EC) AE F032640 00 EC03 BO 25 g/l Emulsifiable concentrate (EC) AE F032640 00 EC11 A3 100 g/l Emulsifiable concentrate (EC) AEF 032640 00 EC02 A8 15 g/l Emulsion, oil in water (EW) AE F032640 00 EW01 B1 15 g/l Suspension concentrate (SC) AE F032640 00 SC02 50 g/l or 25 g/l Ultra low volume (UL) AE F032640 00 UV01 5 g/l Emulsifiable granule (EG) AE F032640 00 EG06 A1 60 g/kg Tablet (TB) AE F032640 00 TB25 A1 250 g/kg Animal health Dip, spray AE F032640 00 WP05 A2 50 g/l Pour-on 7.5 g/l METABOLISM AND ENVIRONMENTAL FATE Animal metabolism Metabolism studies on rats, goats and hens with [14C]deltamethrin and [13,14C]deltamethrin were made available to the Meeting. The metabolism of laboratory animals was reported by the 2000 JMPR as part of a review of the toxicology of deltamethrin and is qualitatively the same as for farm animals. To carry out various metabolism, degradation and toxicological or ecotoxicological studies, the deltamethrin molecule has been labelled on various carbon atoms: [14C-dibromovinyl]deltamethrin labelled on Cv [14C-benzyl]deltamethrin labelled on Cα [14C-cyano]deltamethrin labelled on CN 14 [ C-gem-dimethyl]deltamethrin labelled on (CH3)2 170 deltamethrin 14Cα 14Cv 5 4' Br 3R 1R OαS 3 O * * 2' 2 Br O CN ** * 14CN 14C gem-dimethyl The following Table shows the main degradation products of deltamethrin and the abbreviations used for some metabolites. Table 3. Relationship between abbreviated, common and chemical names, company codes and structural formulae. Common name or Roussel Chemical name (generally CAS) Structural formula abbreviation Uclaf code O CN (S)-α-cyano-3-phenoxybenzyl (1R,3R)-3- Br deltamethrin RU 22974 (2,2-dibromovinyl)-2,2- O dimethylcyclopropanecarboxylate Br O O CN (R)-α-cyano-3-phenoxybenzyl (1R,3R)-3- Br (2,2-dibromovinyl)-2,2- O α-R-deltamethrin RU 23938 dimethylcyclopropanecarboxylate Br O [1R-[1α(S*),3β]]-3-(2,2-dibromoethenyl)- O CN trans- RU 26979 2,2-dimethyl-cyclopropanecarboxylic O Br O deltamethrin acid, cyano(3-phenoxyphenyl)methyl ester Br [1R-[1α(S*),3 α]]-3-(2,2- O O NH2 Br deltamethrin RU 38250 dibromoethenyl)-2,2-dimethyl- O amide cyclopropanecarboxylic acid, 2-amino- 2oxo-1-(3-(phenoxyphenyl)ethyl ester Br O CN [1R-[1α(S*),3α]]-3-(2,2- Br O OH 2-OH- RU 51713 dibromoethenyl)-2,2-dimethyl- O deltamethrin cyclopropanecarboxylic acid, cyano(3-(2- Br O hydroxyphenoxyphenyl)methyl ester deltamethrin 171 Common name or Roussel Chemical name (generally CAS) Structural formula abbreviation Uclaf code CN [1R-[1α(S*),3α]]-3-(2,2- Br O 4-OH- RU 53605 dibromoethenyl)-2,2-dimethyl- O O deltamethrin cyclopropanecarboxylic acid, cyano(3-(4- Br hydroxyphenoxyphenyl)methyl ester OH 3-phenoxybenzaldehyde H mPB aldehyde RU 26684 O O 3-phenoxybenzoic acid OH O mPB acid RU 50293 O 3-phenoxybenzenemethanol O HO mPB alcohol RU 27330 (1R-cis)-3-(2,2-dibromoethenyl)-2,2- Br O dimethylcyclopropanecarboxylic acid (cis) Br2CA RU 23441 Br OH (1R-trans)-3-(2,2-dibromoethenyl)-2,2- Br dimethylcyclopropanecarboxylic acid (trans) Br2CA RU 28302 Br OH O 3-(2-hydroxyphenoxy)benzoic acid OOH O 2'OH mPB acid RU 50961 HO 3-(4-hydroxyphenoxy)benzoic acid O O 4'OH mPB acid RU 46606 HO OH 3-(4-hydroxyphenoxy)benzenemethanol O HO 4'OH mPB RU 46605 alcohol OH Deltamethrin is the [1R,cis; α-S]-isomer of 8 stereoisomeric esters derived from esterification of the dibromo analogue of chrysanthemic acid, 3-(2,2-dibromovinyl)-2,2- dimethylcyclopropanecarboxylic acid (Br2CA) with α-cyano-3-phenoxybenzyl alcohol. Lactating cows. Akhtar et al. (1986) dosed a lactating dairy Holstein 557 kg bw and an Ayrshire 504 kg bw cow with [14C]deltamethrin (gem-dimethyl or benzyl) at 10 mg/kg bw/day for 3 consecutive days. Urine and faeces were collected for each 24-hour period and milk twice daily. The animals were slaughtered 24 hours after the last dose. Radioactivity in all samples was quantified and characterized by TLC and GC. Deltamethrin appeared to be poorly absorbed and mainly eliminated in the faeces (cumulative total 36-43% of the administered dose) within 24 hours of the last dose as deltamethrin(s); 78-82% of 172 deltamethrin the 14C in faeces. The cumulative total for elimination in the urine until 24 hours after the last dose was only 4-6 % of the administered 14C, and 0.42-1.6 % was secreted in the milk. Total deltamethrins were also the major identifiable products in milk (0.10-0.14 mg/kg). The radiocarbon content in various tissues was generally very low (<0.1 mg/kg deltamethrin equivalents) with the exception of liver, kidney, udder, and abdominal and subcutaneous fats. Table 4. Distribution of 14C in the tissues of lactating cows dosed orally with [14C]deltamethrin at 10 mg/kg bw for three consecutive days (Akhtar et al., 1986). [14C]deltamethrin equivalents (mg/kg) Sample gem-dimethyl benzyl Liver 2.2 3.2 Kidney 1.3 2.2 Brain - 0.09 Heart 0.12 0.13 Breast muscle - 0.06 Leg muscle - 0.09 Spleen - 0.08 Udder 0.42 0.62 Lung - 0.21 Abdominal fat 0.28 0.56 Subcutaneous fat 0.40 0.54 Tongue - 0.16 Bile 6.4 21 Table 5. Characterization of 14C in liver, kidney and abdominal fat of lactating cows dosed orally with 14C-gem-dimethyl- or 14C-benzyl-labelled deltamethrin for three consecutive days (% of the TRR) (Akhtar et al., 1986). Compound Liver Kidney Fat gem benzyl gem benzyl gem benzyl Deltamethrin1 24 23 32 35 60 90 Br2CA 23 33 16 mPB aldehyde trace trace trace mPB acid 32 23 Water-soluble 16 10 16 18 Unextractable 37 23 19 24 1 method did not resolve deltamethrin from its isomers, the numbers therefore refer to “total deltamethrin isomers” Degradation of deltamethrin was by cleavage of the ester bond.
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