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Thiamethoxam 1787 Thiamethoxam 1787 THIAMETHOXAM (245) The first draft was prepared by Mr. Denis Hamilton Primary Industries and Fisheries Australia EXPLANATION Thiamethoxam is a nicotinoid compound with broad-spectrum insecticidal properties. It is registered for use on numerous crops in many countries against sucking and chewing insects in vegetables, ornamentals, field crops, deciduous fruits, citrus, cotton and rice. It possesses contact and stomach activity. Its systemic properties has resulted in its use against foliar feeding insects via seed treatment, soil application, through irrigation systems, or applied to the trunks of trees. It is also registered for direct foliar application. The compound was evaluated as a new compound by the 2010 JMPR for both residues and toxicology. The Meeting received information on physical and chemical properties, animal and plant metabolism, environmental fate, analytical methods, storage stability, use patterns, processing, farm animal feedingand supervised residue trials. IDENTITY Thiamethoxam is a nicotinoid compound with broad-spectrum insecticidal properties. ISO common name thiamethoxam Chemical name (EZ)-3-(2-chloro-1,3-thiazol-5-ylmethyl)-5-methyl-1,3,5- IUPAC oxadiazinan-4-ylidene(nitro)amine 3-[(2-chloro-5-thiazolyl)methyl]tetrahydro-5-methyl-N-nitro-4H- CAS 1,3,5-oxadiazin-4-imine CAS Number 153719-23-4 CIPAC Number 637 Synonyms for active CGA 293343 substance: Molecular formula C8H10ClN5O3S Molecular mass 291.71 N O Cl N N Structural formula S N NO2 Thiamethoxam isomers N CH Cl 3 Thiamethoxam is described as an EZ mixture. It is generally believed that NH N S H the activation energy for the EZ interconversion for the C = N bond is CGA 322704 N O low and that an equilibrium mixture is rapidly established at ambient N temperature. O 1788 Thiamethoxam The situation is similar for metabolite CGA 322704. In this case the E form is likely to be favoured in the equilibrium mixture because of possible formation of a hydrogen bond from the secondary amine to the nitro group. The E form of CGA 322704 is equivalent to the compound clothianidin. PHYSICAL AND CHEMICAL PROPERTIES Pure active ingredient: Thiamethoxam Property Result Ref Description (purity 99.7%) Slightly cream, fine crystalline powder, odourless 35446 Melting point, melting range (purity 139.1 ˚C 35441 99.7%) 2.7 10-9 Pa at 20 ˚C Vapour pressure (purity 99.7%), OECD 6.6 10-9 Pa at 25 ˚C. 35445 104 Measurements at 90.5 to 121 ˚C Water solubility (purity 99.7%) at 25 C, 4.1 g/L (pure water, no buffer, measured pH of aqueous phase 35444 OECD 105 7.3) Octanol/water partition coefficient log P = –0.13 (pure water, no buffer, measured pH of aqueous ow 36610 (purity 99.7%) at 25 ˚C, OECD 107 phase 6.9) Hydrolysis rate (purity 99.0%) [14C- pH 9, 25 ˚C: 30 days test; T = 8.8 days ABR-97013 oxadiazin label] 0.5 pH 1, 60 ˚C: 96% remained after 5 days test Hydrolysis rate (purity 99.3%) [14C- pH 5, 60 ˚C: 99% remained after 5 days test ABR-96106 thiazol label] pH 7, 60 ˚C: 5 days test; T0.5 = 8 days Photolysis rate, xenon arc at 410 w/m2 for 12 hours/day, 25 ˚C, 10 mg/L in pH 5 T = 3.1 days ABR-98091 buffer (purity > 99.9%) [14C-thiazol 0.5 label] Dissociation constant in water (purity no dissociation within pH range 2 to 12 38123 99.7%), OECD 112 The hydrolysis of CGA 322704, an important metabolite and hydrolysis product of thiamethoxam was investigated by Ulbrich (1999, 98UL03). CGA 322704 pH 4.2, sterile, dark, 20 ˚C: no decline after 31 days test Hydrolysis rate (radiochemical purity pH 5.1, sterile, dark, 20 ˚C: no decline after 31 days test 98UL03 98.3%) [14C-thiazol label]. Starting pH 7.1, sterile, dark, 20 ˚C: no decline after 31 days test concentration: 5 mg/L. pH 8.9, sterile, dark, 20 ˚C: no decline after 31 days test. Technical material: Thiamethoxam Property Result Ref Description (purity 98.2%) Off-white, fine powder, odourless 58210 Acetone 48 g/L; dichloromethane 110 g/L; Solubility in organic solvents (purity ethyl acetate 7.0 g/L; hexane < 1 mg/L; methanol 13 g/L; 58212 98.2%) at 25 ˚C octanol 620 mg/L; toluene 680 mg/L pH 1, 60 ˚C: 96% remained after 5 days test Hydrolysis rate (purity 98.0%) [14C- pH 5, 60 ˚C: 101% remained after 5 days test ABR-97013 oxadiazin label] pH 7, 25 ˚C: 96% remained after 30 days test pH 9, 40 ˚C: 96 hours test, T0.5 = 28 hours Hydrolysis rate (purity 95.4%) [14C- pH 7, 40 ˚C: 87% remained after 30 days test ABR-97013 oxadiazin label] pH 7, 60 ˚C: 20 days test; T0.5 = 17 days Hydrolysis rate (purity 97.5%) [14C- pH 5, 25 ˚C: 100% remained after 30 days test ABR-96106 thiazol label] pH 9, 25 ˚C: 30 days test; T0.5 = 100 hours pH 7, 60 ˚C: 30 days test; T0.5 = 12 days Hydrolysis rate (purity 97.7%) [14C- pH 9, 40 ˚C: 30 days test; T0.5 = 26 hours ABR-96106 thiazol label] pH 9, 60 ˚C: 17 days test; T0.5 = 3.2 hours Hydrolysis rate (purity 98.4%) [14C- pH 7, 25 ˚C: 98% remained after 30 days test ABR-96106 thiazol label] pH 7, 40 ˚C: 30 days test; T0.5 = 70 days Thiamethoxam 1789 Property Result Ref Photolysis rate, xenon arc at 410 w/m2 for 12 hours/day, 25 ˚C, 10 mg/L in pH 5 T0.5 = 2.3 days ABR-97023 buffer (purity 97.1%) [14C-oxadiazin label] O N N O N Cl Cl Cl NH NH N N N N S S S CGA 322704N N CGA 355190 O NO Thiamethoxam 2 NO2 N N N Cl Cl Cl NH NH HO NH O S 2 S S CGA 309335 N NOA 404617 NH NO2 NO2 Figure 1 Products of thiamethoxam hydrolysis were identified by Lowery (1997, ABR-97013) and Clark (1998, ABR-96106). CGA 309335, CGA 355190 and NOA 404617 were the major products of hydrolysis. CGA 322704 was a minor product. OH O N O Cl NH N NH NH N N N NH N NH S O O O O NH NOA 407475 NH CGA 353042 N N O N O Cl Cl Cl NH NH N N N N S S S N Thiamethoxam N O CGA 322704 NO CGA 355190 NO2 2 O N + COS Cl NH NH + O CNH NH NH2 S isocyanic acid methylurea CGA 353968 O Figure 2 Products of thiamethoxam photolysis were identified by Sparrow (1997, ABR-97023) and Schwartz (1998, ABR-98091). FORMULATIONS The main formulation types are: Code Description Examples FS flowable concentrate for seed treatment 350 g/L, 600 g/L flowable concentrate for seed treatment (includes mefenoxam and FS 258 g/L, 336 g/L fludioxonil) 1790 Thiamethoxam Code Description Examples GR granule (includes pyroquilon) 80 g/kg SC suspension concentrate 240 g/L SC suspension concentrate (includes azoxystrobin) 65 g/L SG water soluble granule 750 g/kg SL soluble concentrate 240 g/L WG water dispersible granule 100 g/kg, 250 g/kg, 300 g/kg, 400 g/kg ZC a mixed formulation of CS and SC (includes lambda-cyhalothrin) 141 g/L A number of products are registered that contain thiamethoxam and another active ingredient, viz., azoxystrobin, fludioxonil, pyroquilon, lambda-cyhalothrin, lufenuron and cyproconazole. METABOLISM AND ENVIRONMENTAL FATE Metabolism and environmental fate studies used thiamethoxam 14C labelled in the guanidine position or in position-2 the thiazole ring. N O N O Cl Cl * N N N N S * S N N NO NO2 2 14 [14C-oxadiazin-4]thiamethoxam [ C-thiazol]thiamethoxam = [14C-guanidine]thiamethoxam Structures, names and codes for metabolites are summarised below. Five possibilities for describing each metabolite are: a simple name, which could be a common name, a simplified systematic name, an abbreviation or a pseudo-common name (e.g. hydroxy-cypermethrin) the systematic chemical name—it may be too cumbersome for use in discussion and tables the CAS number—CAS numbers are not available for many metabolites the company code number, e.g. CGA 322704 serial numbers, e.g., metab 1, metab 2, etc. In this evaluation, metabolites are described by the company code number where available or a metabolite serial number used in the metabolite studies. It should be noted that metabolite serial numbers are not necessarily consistent between studies, e.g. metabolites 4U, 8U and 13U are the same compound. 1-methyl-3-nitroguanidine NO 2 Systematic: N-nitro-N'-methylguanidine NH CAS number: 4245-76-5 N NH Code: NOA 405217 Code: MNG (clothianidin evaluation) 1-methylguanidine NH Systematic: N-methylguanidine NH NH Code: CGA 382191 2 Code: MG (clothianidin evaluation) Thiamethoxam 1791 CGA 265307 N Systematic: N-(2-chlorothiazol-5-ylmethyl)-N'-nitroguanidine Cl NH NH S CAS number: 135018-15-4 NO2 Code: CGA 265307 NH Code: TZNG (clothianidin evaluation) CGA 282149 O Systematic: 3,6-dihydro-3-methyl-N-nitro-2H-1,3,5-oxadiazin-4-amine N NH CAS number: 153719-38-1 N Code: CGA 282149 NO 2 CGA 309335: N Systematic: (2-chlorothiazol-5-yl)-methylamine Cl CAS number: 120740-08-1 S NH2 Code: CGA 309335 CGA 322704 N Cl Systematic: N-(2-chlorothiazol-5-ylmethyl)-N'-methyl-N"-nitroguanidine NH NH S CAS number: 131748-59-9 17 N Code: CGA 322704 Note NO 2 CGA 322704-NO-glucoside OH HO Hydroxylamine glucoside of CGA 322704 CH OH 2 O OH N O Cl N NH S N NO 2 CGA 340575 O Systematic: 3,6-dihydro-N-nitro-2H-1,3,5-oxadiazin-4-amine NH NH CAS number: 123019-22-7 N NO Code: CGA 340575 2 CGA 349208 N Systematic: 2-chloro-5-thiazolemethanol Cl S CH OH CAS number: 145015-15-2 2 Code: CGA 349208 CGA 353042 NH Systematic: 3,6-dihydro-3-methyl-2H-1,3,5-oxadiazin-4-amine Code: CGA 353042 N NH O CGA 353968 N Cl Systematic: 1-(2-chlorothiazol-5-ylmethyl)-3-methylurea NH NH Code: CGA 353968 S O Code: TZMU (clothianidin evaluation) CGA 355190 N O Systematic: 3-(2-chlorothiazol-5-ylmethyl)-5-methyl-[1,3,5]oxadiazinan-4- Cl N N one S Code: CGA 355190 O CGA 359683 N Systematic: 2-chlorothiazole-5-carboxylic acid Cl CAS number: 101012-12-8 S COOH Code: CGA 359683 Code: CTCA (clothianidin evaluation) 17 Note that clothianidin is the E isomer of CGA 322704 ([C(E)]-N-[(2-chloro-5-thiazolyl)methyl]-N'-methyl-N"-nitroguanidine), CAS number 210880-92-5 (formerly 205510-53-8) (Wood, 2010).
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