DPX-E2Y45 - Introducing of a Novel Anthranilamide Insecticide ...

DPX-E2Y45 - Introducing of a Novel Anthranilamide Insecticide ...

Altacor WG Insecticide (DPX-E2Y45) Introducing a Novel Anthranilic Diamide Insecticide from DuPont Daniel W. Sherrod DuPont Crop Protection Memphis Market Memphis, TN Center 38017 DuPont Crop Protection Code: DPX-E2Y45 Common Name: Chlorantraniliprole (ISO) - RynaxypyrTM CAS: 3-Bromo-N-[4-chloro-2-methyl-6[(methylamino)carbonyl]phenyl]-1(3-chloro-2-pyridinyl)-1H-pyrazole-5carboxamide Chemical Structure: Br H H3C Cl N O H N N N O

CH 3 Empirical Formula: C18H14BrCl2N5O2 Molecular Weight: 483.15 g/mole N Cl DuPont Crop Protection Activates Insect Ryanodine Receptors 200 Rynaxypyr EC50 = 40 nM 190 100 140 50 1 min 90 40 17 18 19 20

21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 0 -10

-9 -8 -7 Concentration (log M) -6 -5 Ca2+ Mobilization Threshold ( M) 150 1000 240 50 nM [Ca2+]i Increase (nM) 1 uM Rynaxypyr 2 100 r = 0.91 2 r = 0.84 2

r = 0.84 10 1 P. xylostella 0.1 S. frugiperda H. virescens 0.01 0.001 0.001 0.01 0.1 1 10 Insect LC50 (ppm) Rynaxypyr and related anthranilic diamides stimulate release of Ca2+ stores Rynaxypyr is selective for ryanodine receptors Insecticidal activity is highly correlated with Ca2+ store release 100 1000 DuPont Crop Protection

Does Not Impact Commercialized Targets Targets Below Reflect MoA for > 90% of Commercial Insecticides Excitatory Neuron Muscle OPs Carbamates Na+/K+ channels Pyrethroids Indoxacarb s es n ie il d lo ron c Cy Fip Glut GABA Motor Neuron M oid AChE n i ot ad

c i on inos e N p ACh S Mi to Ins cho ec ndr t ic ide ial s M Insect Neuromuscular Signaling Pathway DuPont Crop Protection What is the Ryanodine Receptor (RyR)? O O N O O CAM O FK BP

CAM BP FK ti n Calcium channel RyR nc Ryanodine (Natural Plant Toxin) cytosol RyR Ju O Ryanodine Receptor Complex in O Chiral Tr i ad O

O lumen CS Q Ca2+ Regulates release of stored calcium Critical for muscle contraction Complex includes accessory proteins Previously, no synthetic RyR agents known with insecticidal properties DuPont Crop Protection Insect Poisoning Symptoms Rapidly Affects Skeletal and Cardiac Muscle Rapid feeding cessation General lethargy Partial paralysis Regurgitation DuPont Crop Protection Resistance Management Baseline Susceptibility Heliothines Australia, Brazil, India, Spain, USA Spodoptera spp. Brazil, Indonesia, Japan, Malaysia, Spain, Thailand, USA, Vietnam

DuPont Crop Protection Effects of DPX-E2Y45 in the Environment Bees Negligible risk in field studies Non-target Insects T1: Negligible toxicity to standard species (mites, parasitoids) + Chrysoperla, Orius T2 to T4: Safety to predatory larvae of Coccinellids and Episyrphus Birds and Mammals Negligible risk Surface water Plants Negligible risk No/low transport to flowering parts Soil Earthworms: Negligible risk Soil Micro: Negligible risk Fish: Negligible risk Algae: Negligible risk Aquatic Inverts: High acute toxicity Moderate chronic

toxicity Sediment Chironomus: Negligible to moderate risk DuPont Crop Protection Mammalian Toxicity E2Y45 exhibits a remarkably favorable toxicity profile Little or no toxicological effects have been observed following single doses as high as 5000 mg/kg bw and following repeat doses as high as ~1500 mg/kg bw/day The low toxicity of this product combined with low use rates provide large margins of safety for consumers and workers DuPont Crop Protection E2Y45: Mammalian Toxicology Lack of adverse effects for the following endpoints: Acute oral, dermal and inhalation toxicity Skin and eye irritation; skin sensitization Genotoxicity in vitro and in vivo

Subacute and subchronic toxicity in rats, mice, and dogs Reproductive and developmental toxicity Neurotoxicity Immunotoxicity Chronic toxicity after 1 year in dogs Chronic toxicity after 1 and 2 years in rats Oncogenicity after 2 years in rats and 18 months in mice DuPont Crop Protection Rynaxypyr Exhibits Insect Receptor Selectivity Insect Receptor: Mammalian Receptor: 120 Single isoform RyR1 skeletal Cell Line PC12 C2C12 IMR32 Source Rat Mouse Human RyR2 cardiac RyR3 non-specific Expressed Isoforms RyR2 & RyR1

RyR1 & RyR3 Not Defined Insect Normalized Response (% of max) Periplaneta 100 Drosophila Heliothis 80 Mammalian 60 C2C12 EC50 = 14 m PC12 EC50 > 100 m IMR32 EC50 > 100 m 350 to >3000X Selectivity 40 20 0

-9.0 -8.0 -7.0 -6.0 -5.0 RynaxypyrTM Concentration (log M) -4.0 DuPont Crop Protection Selectivity to Beneficial Arthropods ORDER Neuroptera FAMILY Chrysopidae SPECIES RATE (g ai/Ha) Chrysoperla carnea 25-100 Mallada signatus 30-60 Coleoptera Coccinellidae Hippodamia sp. 25 Hippodamia variegatta 30 Harmonia axyridis 50-100

Hemiptera Nabidae Nabis kimbergii 30 Anthrocoridae Orius insidiosus 50 Anthocoris nemoralis 60 Lygaeidae Geocoris punctipes 50 Acari Phytoseiidae Amblyseius herbicolus 100 Euseius citrifolius 100 Iphiseiodes zulugai 100 Typhlodromus occidentalis 50-100 Hymenoptera Trichogrammatidae Trichogramma pretiosum 60 Trichogramma chilonis 33 Braconidae Bracon hebetor 50 Dolichogidea tasmanica 30-60 Encyrtidae Ageniaspis citricola 50 Aphelinidae

Aphelinus mali 30-60 no impact, (0-30% mortality); (Ratings according to IOBC/ WPRS Working Group, Hassan et al. 1988). DuPont Crop Protection Pest Spectrum Lepidoptera Noctuidae Heliothines (bollworms, budworms), Earias spp. (bollworms) Spodoptera spp. (armyworms), Agrotis (cutworms) Pseudoplusia, Trichoplusia (loopers) Alabama argillaceae (leaf worms) Tortricidae Argytotaenia, Choristoneura (leafrollers) Carposina,Cydia,Grapholita (fruit moths), Lobesia (berry moths) Crambidae Chilo (stem borers), Ostrinia (corn borers) Hellula (cabbage worms) Lerodea (leaf folders) Leucinodes, Neoleucinodes (fruit borers)

Gelechiidae, Pieridae, Plutellidae Anarsia (twig borers), Tuta, Keiferia (pin worms) Pieris (whites, sulfur) Plutella xylostella (diamondback moth) Gracillariidae Phyllonorycter, Phyllocnistis (leafminers) DuPont Crop Protection Formulations 20 SC 200 g/L suspension concentrate 1.667 lb ai/gal suspension concentrate CoragenTM 35 WG 35% water dispersible granule AltacorTM Formulation Studies Excellent compatibility with other insecticides/fungicides Excellent spray tank clean-out properties Excellent mixing and handling characteristics DuPont Crop Protection Product Attributes Excellent plant protection on a broad spectrum of Lepidoptera and other key pest species, effective at low rates of application Long-lasting protection and rainfast Excellent fit in IPM & IRM programs

Controls insecticide-resistant strains Low toxicity to wildlife such as birds, fish, and mammals DuPont Crop Protection DuPont Rynaxypyr Biological Attributes of A Novel Anthranilic Diamide Insecticide in a New Class of Potent and Selective Ryanodine Receptor Agonists DuPont Crop Protection DuPont RynaxypyrTM Rapid Feeding Cessation Time to feeding cessation (minutes) of S. exigua 3rd instar larvae exposed to dry insecticide residues on treated tomato leaves COMPOUND RynaxypyrTM 20SC Emamectin Benzoate 5WG Methoxyfenozide 2F RATE (ppm) RATE SLOPE SE (g ai/ha) ET 50 (minutes) 167 50

1.85 0.3 7a 40 467 12 140 3.92 1.0 4.45 1.0 170 b 885 c ET 50 CI95% (minutes) 5-9 125 - 219 620 - 1134 ET 50 Ratio (minutes) 24x 126x RynaxypyrTM acts very fast! In this experiment, RynaxypyrTM was signifincalty faster to stop S. exigua larval feeding than Emamectin Benzoate and Methoxyfenozide Data: P. Maron & G. Hannig, Delaware, USA DuPont Crop Protection

DuPont RynaxypyrTM Exceptional Crop Protection RynaxypyrTM 50 GAH E. Benzoate 12 GAH Methoxyfenozide 140 GAH Photos: P. Maron, Delaware, USA UTC DuPont Crop Protection DuPont RynaxypyrTM High Insecticidal Potency Comparative Insecticidal Potency of RynaxypyrTM vs. Commercial Standards against Cydia pomonella neonate larvae (exposure by Ingestion) LC50 (CI95%) (ppm) LC90 (CI95%) (ppm) 4 0.4 (0.3-0.6) 3.1 (2.3-4.7) RynaxypyrTM 35WG

3 0.4 (0.3-0.6) 3.7 (2.4-7.1) Azinphos-methyl 50WP 3 3.9 (2.7-5.1) 28.7 (19.9-49.2) Methoxyfenozide 240SC 2 3.3 (0.2-3.8) 313 (NA) Species Compound Cydia pomonella neonate larvae RynaxypyrTM 20SC Reps RynaxypyrTM is one order of magnitude more potent against Cydia pomonella, when compared to commonly used commercial standards

Data: J. L. Rison et. al., Nambsheim, France DuPont Crop Protection DuPont RynaxypyrTM Ovi-Larvicidal Activity * Anticarsia gemmatalis eggs * Eggs treated with RynaxypyrTM Intoxicated Neonate attempting to get out of the egg Dead Neonate does not complete eclosion RynaxypyrTM has excellent ovi-larvicidal activity RynaxypyrTM is a potent larvicide and will control neonates as they ingest the corion to eclode from the egg Photos: M. Lima, So Paulo, Brazil DuPont Crop Protection DuPont RynaxypyrTM Rainfastness and Residual Activity RynaxypyrTM shows robust rainfastness and residual activity, characteristics which are explained by fundamental biological attributes: Potent insecticidal activity Translaminar movement

Rapid feeding cessation Exceptional crop protection DuPont Crop Protection DuPont RynaxypyrTM In a nutshell . Favorable Toxicological and Eco-toxicological profile Effective and Long-lasting Crop and Yield protection Broad Spectrum Novel mode of action Excellent crop safety Soft on beneficial arthropods Excellent fit into IPM and IRM DuPont Crop Protection Acknowledgments Stanley Royal

Sue Rick Glenn Hammes J. Dan Smith Dickie Edmund Eric Castner Charlie Grymes Danny Tamayo Hugo Ramirez Wayne Steele C. Steve Williams Fred Marmor Paula Marcon Clifton Brister Jay Ellis Dennis Goldsberry DuPont Crop Protection THANK YOU!

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