Chlorantraniliprole

Chlorantraniliprole
	; Chlorantraniliprole 3D molecular model generated using Avogadro software
Names
	Preferred IUPAC name 3-Bromo-N-[4-chloro-2-methyl-6-(methylcarbamoyl)phenyl]-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide
	Other names Rynaxypyr, Coragen, Altacor
Identifiers
CAS Number	500008-45-7;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:67113;
ChEMBL	ChEMBL399318;
ECHA InfoCard	100.112.607
EC Number	610-489-8;
KEGG	C18454;
PubChem CID	11271640;
UNII	622AK9DH9G;
CompTox Dashboard (EPA)	DTXSID2044345 ;
	InChI InChI=1S/C18H14BrCl2N5O2/c1-9-6-10(20)7-11(17(27)22-2)15(9)24-18(28)13-8-14(19)25-26(13)16-12(21)4-3-5-23-16/h3-8H,1-2H3,(H,22,27)(H,24,28) Key: PSOVNZZNOMJUBI-UHFFFAOYSA-N;
	SMILES CC1=C(C(=CC(=C1)Cl)C(=O)NC)NC(=O)C2=CC(=NN2C3=C(C=CC=N3)Cl)Br;
Properties
Chemical formula	C18H14BrCl2N5O2
Molar mass	483.15 g·mol−1
Melting point	209 °C (408 °F; 482 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H319, H335, H410
Precautionary statements	P261, P264, P271, P273, P280, P304+P340, P305+P351+P338, P312, P337+P313, P391, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chlorantraniliprole (Rynaxypyr) is an insecticide of the diamide classe.^[1] Chlorantraniliprole was developed world-wide by DuPont to control a range of pests belonging to the order Lepidoptera (moth), and some Coleoptera (beetle), Diptera (fly), and Isoptera (termite) species.

Chlorantraniliprole opens muscular calcium channels, in particular the ryanodine receptor, rapidly causing paralysis and ultimately death of sensitive species. The differential selectivity chlorantraniliprole has towards insect ryanodine receptors explains its low mammalian toxicity receptor.^[2] Chlorantraniliprole is active on chewing pest insects primarily by ingestion and secondarily by contact.

Chlorantraniliprole is an active ingredient in the insecticidal products Aclepryn (0.2%), Coragen (18.5%), Ferterra (0.4%) and Scotts GrubEx1 (0.08%).

References

^ EPA Pesticides Fact Sheet: Chlorantraniliprole
^ Nauen, Ralf; Steinbach, Denise (27 August 2016). "Resistance to Diamide Insecticides in Lepidopteran Pests". In Horowitz, A. Rami; Ishaaya, Isaac (eds.). Advances in Insect Control and Resistance Management. Cham: Springer (published 26 August 2016). pp. 219–240. ISBN 978-3-319-31800-4.{{cite book}}: CS1 maint: date and year (link)

[1] EPA Pesticides Fact Sheet: Chlorantraniliprole

[2] Nauen, Ralf; Steinbach, Denise (27 August 2016). "Resistance to Diamide Insecticides in Lepidopteran Pests". In Horowitz, A. Rami; Ishaaya, Isaac (eds.). Advances in Insect Control and Resistance Management. Cham: Springer (published 26 August 2016). pp. 219–240. ISBN 978-3-319-31800-4.{{cite book}}: CS1 maint: date and year (link)

[1]

[2]

Names

Chlorantraniliprole 3D molecular model generated using Avogadro software
Preferred IUPAC name 3-Bromo-N-[4-chloro-2-methyl-6-(methylcarbamoyl)phenyl]-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide
Other names Rynaxypyr, Coragen, Altacor
Identifiers
CAS Number	500008-45-7
3D model (JSmol)	Interactive image
ChEBI	CHEBI:67113
ChEMBL	ChEMBL399318
ECHA InfoCard	100.112.607
EC Number	610-489-8
KEGG	C18454
PubChem CID	11271640
UNII	622AK9DH9G
CompTox Dashboard (EPA)	DTXSID2044345
InChI InChI=1S/C18H14BrCl2N5O2/c1-9-6-10(20)7-11(17(27)22-2)15(9)24-18(28)13-8-14(19)25-26(13)16-12(21)4-3-5-23-16/h3-8H,1-2H3,(H,22,27)(H,24,28) Key: PSOVNZZNOMJUBI-UHFFFAOYSA-N
SMILES CC1=C(C(=CC(=C1)Cl)C(=O)NC)NC(=O)C2=CC(=NN2C3=C(C=CC=N3)Cl)Br
Properties
Chemical formula	C₁₈H₁₄BrCl₂N₅O₂
Molar mass	483.15 g·mol⁻¹
Melting point	209 °C (408 °F; 482 K)
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H319, H335, H410
Precautionary statements	P261, P264, P271, P273, P280, P304+P340, P305+P351+P338, P312, P337+P313, P391, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references