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CYANTRANILIPROLE (263) the First Draft Was Prepared by Mr. David Lunn New Zealand Food Safety Authority, Wellington, New Zealand

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CYANTRANILIPROLE (263) the First Draft Was Prepared by Mr. David Lunn New Zealand Food Safety Authority, Wellington, New Zealand Cyantraniliprole 361 CYANTRANILIPROLE (263) The first draft was prepared by Mr. David Lunn New Zealand Food Safety Authority, Wellington, New Zealand EXPLANATION Cyantraniliprole is a diamide insecticide with a mode of action (ryanodine receptor activation) similar to chlorantraniliprole and flubendiamide. It has root systemic activity with some translaminar movement and is effective against the larval stages of lepidopteran insects; and also on thrips, aphids, and some other chewing and sucking insects. Authorisations exist for the use of cyantraniliprole in Canada, Columbia, Malaysia, New Zealand, Vietnam and the CLISS countries in West Africa. Authorisations are also being progressed in Australia, Europe and USA under an OECD Joint Review exercise. Cyantraniliprole was scheduled by the Forty-fourth Session of the CCPR as a new compound for consideration by the 2013 JMPR. Residue and analytical aspects of cyantraniliprole were considered for the first time by the present meeting. The manufacturer submitted studies on metabolism, analytical methods, supervised field trials, processing, freezer storage stability, environmental fate in soil and rotational crop residues. In this evaluation, the values presented in the tables are as reported in the various studies, but in the accompanying text, they have generally been rounded to two significant digits. Abbreviations have also been used for the various cyantraniliprole metabolites mentioned in the study reports. These include: IN-F6L99 3-Bromo-N-methyl-1H-pyrazole-5-carboxamide IN-HGW87 N-[2-(Aminocarbonyl)-4-cyano-6-methylphenyl]-3-bromo-1-(3-chloro-2- pyridinyl)-1H-pyrazole-5-carboxamide IN-J9Z38 2-[3-Bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]-3,4-dihydro-3,8- dimethyl-4-oxo-6-quinazolinecarbonitrile IN-JCZ38 4-[[[3-Bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]carbonyl]amino]- N′3′,5-dimethyl-1,3-benzenedicarboxamide IN-K7H19 4-[[[3-Bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]carbonyl]amino]-5- methyl-1,3-benzenedicarboxamide IN-MLA84 2-[3-Bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]-1,4-dihydro-8- methyl-4-oxo-6-quinazolinecarbonitrile IN-MYX98 3-Bromo-1-(3-chloro-2-pyridinyl)-N-[4-cyano- 2[[(hydroxymethyl)amino]carbonyl]-6-methylphenyl]-1H-pyrazole-5- carboxamide IN-N5M09 6-Chloro-4-methyl-11-oxo-11H-pyrido[2,1-b]quinazoline-2-carbonitrile IN-N7B69 3-Bromo-1-(3-chloro-2-pyridinyl)-N-[4-cyano-2-(hydroxymethyl)-6- [(methylamino)carbonyl]phenyl]-1H-pyrazole-5-carboxamide 362 Cyantraniliprole IDENTITY ISO common name: Cyantraniliprole Code number DPX-HGW86, SYN545377 IUPAC name: 3-bromo-1-(3-chloro-2-pyridyl)-4Ą-cyano-2Ą-methyl-6Ą- (methylcarbamoyl)pyrazole-5-carboxanilide Chemical Abstracts name: 3-bromo-1-(3-chloro-2-pyridinyl)-N-[4-cyano-2-methyl-6-[(methylamino)carbonyl] phenyl]-1H-pyrazole-5-carboxamide CAS number 736994-63-1 CIPAC number not allocated Molecular mass: 473.72 g/mol Molecular formula C19H14BrClN6O2 Structural formula: O N CH N 3 H O N Br H CH3 N N N Cl PHYSICAL AND CHEMICAL PROPERTIES Pure active ingredient Property Findings Reference Test Item DPX-HGW86-209 DPX-HGW86-412 DPX-HGW86-141 (98.4% purity) (97% purity) (93.3% purity) Melting point 217-219 °C DP-27440 Boiling point 232 °C DP-27440 Relative density 1.497 1.496 DP-18863 (20°C) 1.384 DP-27440 Vapour pressure 5.133 × 10–15 Pa (20 °C) DP-17052 (extrapolated) 1.787 × 10–14 Pa (25 °C) < 6.15 × 10–8 Pa (80 °C) Henry's law 1.7 ×10–13 Pa m3 mol–1 (20 °C) DP-18861 constant (calculated) Appearance white powder, no noticeable odour DP-18863 DP-27440 pH (1% 5.61 DP-19177 dispersion) Cyantraniliprole 363 Property Findings Reference Test Item DPX-HGW86-209 DPX-HGW86-412 DPX-HGW86-141 (98.4% purity) (97% purity) (93.3% purity) Solubility in water pH 4 17.43 mg/L DP-17050 (20 °C) pH 7 12.33 mg/L pH 9 5.94 mg/L) In pure (Milli-RO) water: pH 7.2 14.23 mg/L Solubility in acetone 6.54 g/L DP-27447 organic solvents ethyl acetate 1.96 g/L (20°C) dichloromethane 5.05 g/L n-octanol 0.79 g/L methanol 4.73 g/L n-hexane 0.00007 g/L o-xylene 0.29 g/L acetonitrile 2.45 g/L n-Octanol/water log Pow 1.94 at 22 °C (shake flask method) DP-17054 partition Not pH-dependant (pH 4–9) coefficient Hydrolysis Hydrolysis of cyantraniliprole (99% purity) is pH and temperature DP-17058 (sterile buffer dependant: solutions, [cyano- 14 C] and [pyrazole DT50 (days) DT90 (days) carbonyl-14C] 15 °C 25 °C 35 °C 15 °C 25 °C 35 °C radiolabels pH 4 362 212 55.2 1204 705 183 pH 7 126 30.3 7.51 417 101 25 pH 9 3.1 0.85 0.58 10.3 2.82 1.91 IN-J9Z38 is the major hydrolysis product accounting for up to 28% AR (pH 4), 89% AR (pH 7) and 98% AR (pH 9). Estimated degradation rates: DT50 (days) @ 35 °C DT90 (days) @ 35 °C pH 7 227 755 pH 9 376 1248 Photolysis Cyantraniliprole is rapidly degraded by photolysis. Degradation rates in DP-17060 [CN-14C] and [PC- natural water and pH 4 sterile buffer at 25 °C, exposed to continuous 14C] radiolabels artificial sunlight for 15 days are: purity > 98% DT50 (days) DT90 (days) pH 4 buffer 0.17 0.57 natural water 0.22 0.72 Degradation products include four major (> 5% AR) degradation products (IN-NXX69, IN-QKV54, IN-NXX70, IN-QKV55). Quantum yield: (φ)=1.195 × 10–4 molecules degraded/photon Dissociation pKa=8.8 at 20 °C (pH range of 2–11, wavelength of 316 nm) DP-19176 constant 364 Cyantraniliprole Formulations Formulations of cyantraniliprole are available for use as foliar applications and soil or seed treatments. Formulation type Active substance/s and content Application type OD (Oil Dispersion) Cyantraniliprole 100 g/L Foliar applications SC (Soluble Concentrate) Cyantraniliprole 200 g/L Soil and seed treatments FS (Flowable suspension Cyantraniliprole 625 g/L Seed treatment METABOLISM AND ENVIRONMENTAL FATE The Meeting received cyantraniliprole metabolism studies on animals (rats, lactating goats and laying hens), plants, soil and rotational crops. Cyantraniliprole radiolabelled on the 4-cyano or the pyrazole carbonyl groups were used in these studies. The label positions are given below: O O NHCH NHCH NC 3 NC 3 * O O N N # H Br H Br CH N CH N 3 N N 3 N N Cl Cl [CN-14C]-cyantraniliprole (CN-label) [PC-14C]-cyantraniliprole (PC-label) *=location of the radiolabel #=location of the radiolabel Major metabolites identified in these studies and discussed in this evaluation are listed below. Table 1 Major cyantraniliprole metabolites identified in plant, animal and soil matrices Codes Names Molecular formula Occurrence DPX-HGW86 3-Bromo-1-(3-chloro-2-pyridinyl)-N-[4- sediment cyano-2-methyl-6- Br soil [(methylamino)carbonyl]phenyl]-1H- HN O hydrolysis pyrazole-5-carboxamide H N photolysis N N plants Cl rat O livestock N water N Bis hydroxy DPX- 3-Bromo-1-(3-chloro-2-pyridinyl)-N-[4- HO rat HGW86 cyano-2-(hydroxymethyl)-6- Br poultry [[(hydroxymethyl)amino]carbonyl]phenyl]- O NH 1H-pyrazole-5-carboxamide H N N N O Cl N N OH Cyantraniliprole 365 Codes Names Molecular formula Occurrence IN-DBC80 3-Bromo-1-(3-chloro-2-pyridinyl)-1H- O Soil pyrazole-5-carboxylic acid rat urine HO Br livestock N N N Cl IN-F6L99 3-Bromo-N-methyl-1H-pyrazole-5- Br soil carboxamide high temperature HN hydrolysis N N O H IN-HGW87 N-[2-(Aminocarbonyl)-4-cyano-6- Br Plants methylphenyl]-3-bromo-1-(3-chloro-2- rat O NH pyridinyl)-1H-pyrazole-5-carboxamide 2 livestock H N N N O Cl N N IN-J9Z38 2-[3-Bromo-1-(3-chloro-2-pyridinyl)-1H- Br Sediment pyrazol-5-yl]-3,4-dihydro-3,8-dimethyl-4- degradation oxo-6-quinazolinecarbonitrile O soil N N hydrolysis N photolysis N Cl plants N livestock N rat IN-JCZ38 4-[[[3-Bromo-1-(3-chloro-2-pyridinyl)-1H- Sediment pyrazol-5-yl]carbonyl]amino]-N′3′,5- degradation HN Br dimethyl-1,3-benzenedicarboxamide O soil H plants N N livestock O N O Cl N NH2 IN-JSE76 4-[[[3-Bromo-1-(3-chloro-2-pyridinyl)-1H- Sediment pyrazol-5-yl]carbonyl]amino]-3-methyl-5- HN Br degradation [(methylamino)carbonyl]benzoic acid O soil H plants N N livestock N O O Cl N OH 366 Cyantraniliprole Codes Names Molecular formula Occurrence IN-K5A77 2-[3-Bromo-1-(3-chloro-2-pyridinyl)-1H- Br Sediment pyrazol-5-yl]-3,4-dihydro-3,8-dimethyl-4- degradation O oxo-6-quinazolinecarboxamide N soil N plants N livestock N Cl O N H2N IN-K5A78 2-[3-Bromo-1-(3-chloro-2-pyridinyl)-1H- Br Sediment pyrazol-5-yl]-3,4-dihydro-3,8-dimethyl-4- O degradation N oxo-6-quinazolinecarboxylic acid N soil N plants N livestock O Cl N OH IN-K5A79 3-(Aminocarbonyl)-4-[[[3-bromo-1-(3- Sediment H2N O Br chloro-2-pyridinyl)-1H-pyrazol-5- degradation yl]carbonyl]amino]-5-methylbenzoic acid H soil N N plants O N livestock O Cl HO N IN-K7H19 4-[[[3-Bromo-1-(3-chloro-2-pyridinyl)-1H- Br Soil pyrazol-5-yl]carbonyl]amino]-5-methyl- H2N O plants 1,3-benzenedicarboxamide H livestock N N N O O Cl N NH2 IN-M2G98 3-Bromo-1-(3-chloro-2-pyridinyl)-1H- O Soil degradation pyrazole-5-carboxylic acid, amide H N 2 Br N N N Cl IN-MLA84 2-[3-Bromo-1-(3-chloro-2-pyridinyl)-1H- Br Plants pyrazol-5-yl]-1,4-dihydro-8-methyl-4-oxo- livestock O H 6-quinazolinecarbonitrile N N rat N N Cl N N Cyantraniliprole 367 Codes Names Molecular formula Occurrence IN-MLA84 2-[3-Bromo-1-(3-chloro-2-pyridinyl)-1H- Br Plants carboxylic acid pyrazol-5-yl]-6-cyano-1,4-dihydro-4-oxo- rat O H 8-quinazolinecarboxylic acid N N poultry N N Cl N N O OH Hydroxy-IN- 2-[3-Bromo-1-(3-chloro-2-pyridinyl)-1H- Br Poultry MLA84 pyrazol-5-yl]-3,4-dihydro-8- O H (hydroxymethyl)-4-oxo-6- N N quinazolinecarbonitrile N N Cl N N OH Hydroxy-IN- 2-[3-Bromo-1-(3-chloro-2-pyridinyl)-1H- O Plants N MLA84 glucoside pyrazol-5-yl]-8-[(-D- glucopyranosyloxy)methyl]-1,4-dihydro-4- NH oxo-6-quinazolinecarbonitrile N Br N N N O O HO OH Cl HO OH
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