altacor™ wg insecticide (dpx-e2y45) introducing a novel anthranilic diamide insecticide from...
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Altacor™ WG Insecticide(DPX-E2Y45) Introducing
a Novel Anthranilic Diamide Insecticide from DuPont
Daniel W. Sherrod DuPont Crop Protection
Memphis Market Center
Memphis, TN 38017
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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-5-carboxamide
Chemical Structure:
NH
NH
O
O
NN
N
Br
Cl
Cl
CH3
CH3
Empirical Formula: C18H14BrCl2N5O2
Molecular Weight: 483.15 g/mole
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Activates Insect Ryanodine Receptors
40
90
140
190
240
17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37
1 min
50 n
M
40
90
140
190
240
17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37
1 min
50 n
M
1 min
50 n
M1 uM
Rynaxypyr
Concentration (log M)
[Ca2+
] iI n
c rea
se (
nM)
0
50
100
150
200
-10 -9 -8 -7 -6 -5
Rynaxypyr™ EC50 = 40 nMr2 = 0.84
r2 = 0.91r2 = 0.84
0.001
0.01
0.1
1
10
100
1000
0.001 0.01 0.1 1 10 100 1000
P. xylostella
S. frugiperda
H. virescens
Insect LC50 (ppm)
Ca2+
Mob
iliza
tion
Thr
esho
ld (
M)
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
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Does Not Impact Commercialized Targets
Targets Below Reflect MoA for > 90% of Commercial Insecticides
ACh
Excitatory Neuron
Motor Neuron
Muscle
GABA
Glut
AChE
Na+/K+
channels
M
M
OPsCarbamates
Mitochondrial
InsecticidesNeonicotinoids
Spinosad
PyrethroidsIndoxacarb
Cyclodienes
Fipro
nil
Insect Neuromuscular Signaling Pathway
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What is the Ryanodine Receptor (RyR)?
Calcium channel
Regulates release of stored calcium
Critical for muscle contraction
Complex includes accessory proteins
Previously, no synthetic RyR agents known with insecticidal properties
Ca2+
FKBPFKBP
Triad
in
Junctin
lumen
cytosol
CAM CAM
RyanodineReceptor Complex
CSQ
RyR RyR
O
O
O
O
O
O
O
O
O
N
Chiral
O
O
O
O
O
O
O
O
O
N
Chiral
Ryanodine(Natural Plant Toxin)
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Rapidly Affects Skeletal and Cardiac Muscle
Rapid feeding cessation
General lethargy
Partial paralysis
Regurgitation
Insect Poisoning Symptoms
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Resistance ManagementBaseline Susceptibility
Heliothines Australia, Brazil, India, Spain, USA
Spodoptera spp. Brazil, Indonesia, Japan, Malaysia, Spain,
Thailand, USA, Vietnam
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Effects of DPX-E2Y45 in the Environment
Soil
Surface water
Birds and Mammals• Negligible risk
Bees • Negligible risk in field studies
• 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
Non-target Insects
• T1: Negligible toxicity to standard species (mites, parasitoids) + Chrysoperla, Orius
• T2 to T4: Safety to predatory larvae of Coccinellids and Episyrphus
Plants
• Negligible risk• No/low transport
to flowering parts
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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
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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
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350 to >3000XSelectivity
Rynaxypyr™ Exhibits Insect Receptor Selectivity
Insect Receptor: Single isoform
Mammalian Receptor: RyR1 – “skeletal” RyR2 – “cardiac” RyR3 – “non-specific”
Cell Line Source Expressed IsoformsPC12 Rat RyR2 & RyR1
C2C12 Mouse RyR1 & RyR3IMR32 Human Not Defined
No
rmal
ized
Res
po
nse
(% o
f m
ax)
RynaxypyrTM Concentration (log M)
0
20
40
60
80
100
120
-9.0 -8.0 -7.0 -6.0 -5.0 -4.0
InsectPeriplaneta
Drosophila
Heliothis
MammalianC2C12 EC50 = 14 m
PC12 EC50 > 100 m
IMR32 EC50 > 100 m
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ORDER FAMILY SPECIES RATE (g ai/Ha)
Neuroptera Chrysopidae 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).
Selectivity to Beneficial Arthropods
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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)
Pest Spectrum – Lepidoptera
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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
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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
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DuPont Rynaxypyr™
Biological Attributes
of A Novel Anthranilic Diamide Insecticide in a
New Class of Potent and Selective Ryanodine Receptor
Agonists
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RynaxypyrTM acts very fast! In this experiment, RynaxypyrTM was signifincalty faster to stop S. exigua larval feeding than Emamectin Benzoate and Methoxyfenozide
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
RynaxypyrTM 20SC 167 50 1.85 ± 0.3 7 a 5 - 9 -
Emamectin Benzoate 5WG 40 12 3.92 ± 1.0 170 b 125 - 219 24x
Methoxyfenozide 2F 467 140 4.45 ± 1.0 885 c 620 - 1134 126x
ET50 Ratio(minutes)
ET50
(minutes) COMPOUND
RATE (g ai/ha)
SLOPE ± SERATE (ppm)
ET50 CI95%
(minutes)
Data: P. Marçon & G. Hannig, Delaware, USA
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DuPont RynaxypyrTM
Exceptional Crop Protection
RynaxypyrTM
50 GAH
Methoxyfenozide 140 GAH
E. Benzoate12 GAH
UTC
Photos: P. Marçon, Delaware, USA
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DuPont RynaxypyrTM
High Insecticidal Potency
RynaxypyrTM is one order of magnitude more potent against Cydia pomonella, when compared to commonly used commercial standards
Comparative Insecticidal Potency of RynaxypyrTM vs. Commercial Standards against Cydia pomonella neonate larvae (exposure by Ingestion)
RynaxypyrTM 20SC 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)
Cydia pomonellaneonate larvae
LC90 (CI95%) (ppm)
Species Compound LC50 (CI95%) (ppm)
Reps
Data: J. L. Rison et. al., Nambsheim, France
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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
* Eggs treated with RynaxypyrTM
Intoxicated Neonate attempting to get out of the egg
Dead Neonate does not complete eclosion
* Anticarsia gemmatalis eggs
DuPont RynaxypyrTM Ovi-Larvicidal Activity
Photos: M. Lima, São Paulo, Brazil
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COTTON – RESCUE APPLICATION Heliothine populations were allowed to hatch and
develop into populations ranging in age up to 3-6 day old larvae prior to application. Key learning's center on the 3 to 5 and 6 to 8 DAT evaluations to determine the knockdown effects of E2Y45 on an established population of Heliothines.
Evaluations at 3 to 5 DAT had significant terminal damage with all treatments due to the delay in application. E2Y45 at 0.066 and 0.088 lb ai/ac resulted in similar protection with a significant reduction in terminal damage observed by 6 to 8 DAT.
Reduction in square damage ranged from 85% to 90% for all rates of E2Y45 at 6 to 8 DAT. Overall, less terminal, square, and boll damage was observed with E2Y versus Tracer when used in a rescue situation.
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COTTON – RESCUE APPLICATION
Yields of lint/ac with E2Y at 0.066 and 0.088 lb ai/ac (2 trials) were 210 to 290 lbs greater than Tracer and 520 to 600 lbs greater than the UTC.
This data supports excellent knockdown control with E2Y45 at the 0.066 and 0.088 lb ai/ac rates.
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COTTON – RESIDUAL CONTROL
3 - 4 DAT : E2Y45 at rates of 0.066 and 0.088 lb ai/ac were equal in performance and provided good to excellent insect control and damage reduction ratings. Efficacy was slightly lower with the 0.044 lbai/ac rate of E2Y45 which performed similar to the standard, Tracer.
7 DAT: control of live larvae in the terminals and squares was excellent with E2Y45 at 0.088 lb ai/ac. Reduction in terminal and square damage was similar with all rates of E2Y45 at 7 DAT. Overall, E2Y45 performance exceeded that of Tracer at this evaluation period.
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COTTON – RESIDUAL CONTROL
10-11 DAT: E2Y45 at 0.088 lb ai/ac continued to provide good control of terminal larvae (83%) and excellent control of square larvae (93%). Control of square larvae was similar between the 0.088 and 0.066 lbai/ac rates with both exceeding 0.044 lbai/ac. Reduction in terminal and square damage was similar with all rates of E2Y45 at 7 DAT. Overall, E2Y45 performance exceeded that of Tracer at this evaluation period.
14-17 DAT: E2Y45 at 0.088 lb ai/ac provided the highest level of insect control and fruit protection. Overall performance declined with the 0.066 and 0.044 lbai/ac rates of E2Y45. Tracer performance dropped significantly.
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COTTON – HELIOTHINE CONTROL E2Y45 at 0.044 lbai/ac provides insect control and plant protection equivalent to, to slightly better than Tracer. At 0.044 lbaia/c, the residual control seems greater than Tracer and a trend is present for better yields.
Limited data is available comparing E2Y45 at 0.066 lbai/ac to Tracer (3 trials). Data supports better performance versus Tracer at this rate.
E2Y45 at 0.088 lbai/ac provides significantly greater insect control, plant protection and offers longer residual when compared to Tracer at 0.067 lbai/ac. In nine trials with direct comparisons, the average yield increase with this rate is 57% which is 17% greater than Tracer’s average.
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COTTON – HELIOTHINE CONTROL
When compared to BG II, 0.088 lbai/ac of E2Y45 provides equivalent insect control and fruit protection and has averaged 8% more yield versus BG II.
Limited data collected in 2004 for the 0.066 lbai/ac rate of E2Y45 (1-2 data points per evaluation) supported insect control and damage ratings slightly less than BG II. The 0.044 lbai/ac rate of E2Y45 did not provide control equivalent to BG II.
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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
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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 Programs
DuPont RynaxypyrTM
In a nutshell ….
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• Stanley Royal• Sue Rick• Glenn Hammes• J. Dan Smith• Dickie Edmund• Eric Castner• Charlie Grymes• Danny Tamayo• Hugo Ramirez• Wayne Steele• C. Steve Williams
Acknowledgments
• Fred Marmor• Paula Marcon• Clifton Brister• Jay Ellis• Dennis Goldsberry
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THANK YOU!