Indoxacarb

Last updated
Indoxacarb
Indoxacarb.svg
Names
Preferred IUPAC name
Methyl 7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4-(trifluoromethoxy)phenyl]amino]carbonyl]indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylate
Systematic IUPAC name
(S)-Methyl 7-chloro-2-{[(methoxycarbonyl)[4-(trifluoromethoxy)phenyl]amino]carbonyl}-2H,3H,4aH,5H-indeno[1,2-e][1,3,4]oxadiazine-4a-carboxylate
Identifiers
3D model (JSmol)
AbbreviationsDPX-MP062
8366683
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.132.370 OOjs UI icon edit-ltr-progressive.svg
KEGG
MeSH Indoxacarb
PubChem CID
UNII
UN number UN 3077
  • InChI=1S/C22H17ClF3N3O7/c1-33-18(30)21-10-12-9-13(23)3-8-16(12)17(21)27-28(11-35-21)19(31)29(20(32)34-2)14-4-6-15(7-5-14)36-22(24,25)26/h3-9H,10-11H2,1-2H3
    Key: VBCVPMMZEGZULK-UHFFFAOYSA-N
  • COC(=O)N(C(=O)N1COC2(C(=O)OC)Cc3cc(Cl)ccc3C2=N1)c1ccc(OC(F)(F)F)cc1
Properties
C22H17ClF3N3O7
Molar mass 527.84 g·mol−1
Melting point 88.1 °C (190.6 °F; 361.2 K) 99% indoxacarb PAI
Pharmacology
QP53AX27 ( WHO )
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Indoxacarb is an oxadiazine pesticide developed by DuPont that acts against lepidopteran larvae. [1] It is marketed under the names Indoxacarb Technical Insecticide, Steward Insecticide and Avaunt Insecticide. It is also used as the active ingredient in the Syngenta line of commercial pesticides: Advion and Arilon. [2] [3] [4]

Contents

Its main mode of action is via blocking of neuronal sodium channels, belonging to IRAC group 22A. [1] It is fairly lipophilic with a Kow of 4.65. This pesticide should be used with caution since some insects such as the oriental tobacco budworm (Helicoverpa assulta) become resistant when exposed. [5]

In 2021, the European Union [6] chose not to renew Indoxacarb for use as a plant-protection insecticide. The United Kingdom still allows use of the compound until 2025. [7]

Development

Indoxacarb was developed by the McCann et al. team at E. I. du Pont de Nemours. [8] [9]

Household products

Indoxacarb is the active ingredient in a number of household insecticides, including cockroach and ant baits, and can remain active after digestion. [10] In 2012 DuPont's Professional Products including the line of Advion and Arilon products was purchased by Syngenta. [11] Indoxacarb is the active ingredient in the pet product, Activyl, from Merck Animal Health. It is marketed to kill fleas on dogs and cats. [12]

Toxicity to humans

While toxicity to humans has not been formally studied, there is a reported case of a person consuming indoxacarb in a suicide attempt. [13] The patient developed methemoglobinemia following ingestion. [13] Methemoglobinemia (also known as blue baby syndrome) is a condition which ultimately decreases the effectiveness of red blood cells to exchange oxygen with organs. Methemoglobinemia can be fatal if left untreated, however when the cause is exposure to a chemical agent (not genetic) a variety of treatments are available and effective. [14] [15]

Related Research Articles

<span class="mw-page-title-main">Pesticide</span> Substance used to destroy pests

Pesticides are substances that are used to control pests. They include herbicides, insecticides, nematicides, fungicides, and many others. The most common of these are herbicides, which account for approximately 50% of all pesticide use globally. Most pesticides are used as plant protection products, which in general protect plants from weeds, fungi, or insects. In general, a pesticide is a chemical or biological agent that deters, incapacitates, kills, or otherwise discourages pests. Target pests can include insects, plant pathogens, weeds, molluscs, birds, mammals, fish, nematodes (roundworms), and microbes that destroy property, cause nuisance, or spread disease, or are disease vectors. Along with these benefits, pesticides also have drawbacks, such as potential toxicity to humans and other species.

<span class="mw-page-title-main">Insecticide</span> Pesticide used against insects

Insecticides are pesticides used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. The major use of insecticides is in agriculture, but they are also used in home and garden settings, industrial buildings, for vector control, and control of insect parasites of animals and humans.

<span class="mw-page-title-main">Sodium nitrite</span> Chemical compound

Sodium nitrite is an inorganic compound with the chemical formula NaNO2. It is a white to slightly yellowish crystalline powder that is very soluble in water and is hygroscopic. From an industrial perspective, it is the most important nitrite salt. It is a precursor to a variety of organic compounds, such as pharmaceuticals, dyes, and pesticides, but it is probably best known as a food additive used in processed meats and in fish products.

<span class="mw-page-title-main">Bifenthrin</span> Chemical compound

Bifenthrin is a pyrethroid insecticide. It is widely used against ant infestations.

<span class="mw-page-title-main">Pyrethroid</span> Class of insecticides

A pyrethroid is an organic compound similar to the natural pyrethrins, which are produced by the flowers of pyrethrums. Pyrethroids are used as commercial and household insecticides.

<span class="mw-page-title-main">Fenvalerate</span> Chemical compound

Fenvalerate is a synthetic pyrethroid insecticide. It is a mixture of four optical isomers which have different insecticidal activities. The 2-S alpha configuration, known as esfenvalerate, is the most insecticidally active isomer. Fenvalerate consists of about 23% of this isomer.

<span class="mw-page-title-main">Agrochemical</span> Any chemical used in agriculture

An agrochemical or agrichemical, a contraction of agricultural chemical, is a chemical product used in industrial agriculture. Agrichemical typically refers to biocides alongside synthetic fertilizers. It may also include hormones and other chemical growth agents. Though the application of mineral fertilizers and pesticidal chemicals has a long history, the majority of agricultural chemicals were developed from the 19th century, and their use were expanded significantly during the Green Revolution and the late 20th century. Agriculture that uses these chemicals is frequently called conventional agriculture.

<span class="mw-page-title-main">Syngenta</span> Global provider of agricultural science and technology

Syngenta Global AG is a global agricultural technology company headquartered in Basel, Switzerland. It primarily covers crop protection and seeds for farmers. Syngenta is part of the Syngenta Group, entirely owned by Sinochem, a Chinese state-owned enterprise.

<span class="mw-page-title-main">Azinphos-methyl</span> Chemical compound

Azinphos-methyl (Guthion) is a broad spectrum organophosphate insecticide manufactured by Bayer CropScience, Gowan Co., and Makhteshim Agan. Like other pesticides in this class, it owes its insecticidal properties to the fact that it is an acetylcholinesterase inhibitor. It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act, and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.

Acibenzolar-<i>S</i>-methyl Chemical compound

Acibenzolar-S-methyl is the ISO common name for an organic compound that is used as a fungicide. Unusually, it is not directly toxic to fungi but works by inducing systemic acquired resistance, the natural defence system of plants.

<span class="mw-page-title-main">Azoxystrobin</span> Chemical compound

Azoxystrobin is a broad spectrum systemic fungicide widely used in agriculture to protect crops from fungal diseases. It was first marketed in 1996 using the brand name Amistar and by 1999 it had been registered in 48 countries on more than 50 crops. In the year 2000 it was announced that it had been granted UK Millennium product status.

<span class="mw-page-title-main">Cyhalothrin</span> Synthetic pyrethroid used as insecticide

Cyhalothrin is an organic compound that, in specific isomeric forms, is used as a pesticide. It is a pyrethroid, a class of synthetic insecticides that mimic the structure and properties of the naturally occurring insecticide pyrethrin which is present in the flowers of Chrysanthemum cinerariifolium. Pyrethroids, such as cyhalothrin, are often preferred as an active ingredient in agricultural insecticides because they are more cost-effective and longer acting than natural pyrethrins. λ-and γ-cyhalothrin are now used to control insects and spider mites in crops including cotton, cereals, potatoes and vegetables.

<span class="mw-page-title-main">Methomyl</span> Chemical compound

Methomyl is a carbamate insecticide introduced in 1966. It is highly toxic to humans, livestock, pets, and wildlife. The EU imposed a pesticide residue limit of 0,01 mg/kg for all fruit and vegetables.

<span class="mw-page-title-main">Phoxim</span> Chemical compound

Phoxim is an organophosphate insecticide that is produced by the Bayer corporation. It is an analogous dimethyl ester and an organothiophosphate acaricide. It is allowed for use in limited applications in the European Union. It is banned for use on crops in the European Union since 22 December 2007.

<i>Helicoverpa assulta</i> Species of moth

Helicoverpa assulta, the oriental tobacco budworm, is a moth of the family Noctuidae. H. assulta adults are migratory and are found all over the Old World Tropics including Asia, Africa, and Australia.

<span class="mw-page-title-main">Thiamethoxam</span> Chemical compound

Thiamethoxam is the ISO common name for a mixture of cis-trans isomers used as a systemic insecticide of the neonicotinoid class. It has a broad spectrum of activity against many types of insects and can be used as a seed dressing.

<span class="mw-page-title-main">Tefluthrin</span> Synthetic pyrethroid used as insecticide

Tefluthrin is the ISO common name for an organic compound that is used as a pesticide. It is a pyrethroid, a class of synthetic insecticides that mimic the structure and properties of the naturally occurring insecticide pyrethrin which is present in the flowers of Chrysanthemum cinerariifolium. Pyrethroids such as tefluthrin are often preferred as active ingredients in agricultural insecticides because they are more cost-effective and longer acting than natural pyrethrins. It is effective against soil pests because it can move as a vapour without irreversibly binding to soil particles: in this respect it differs from most other pyrethroids.

<span class="mw-page-title-main">Diamide insecticides</span> Class of insecticide

Diamide insecticides are a class of insecticides, active mainly against lepidoptera (caterpillars), which act on the insect ryanodine receptor. They are diamides of either phthalic acid or anthranilic acid, with various appropriate further substitutions.

<span class="mw-page-title-main">Sulfoxaflor</span> Chemical compound

Sulfoxaflor, also marketed as Isoclast, is a systemic insecticide that acts as an insect neurotoxin. A pyridine and a trifluoromethyl compound, it is a member of a class of chemicals called sulfoximines, which act on the central nervous system of insects.

<span class="mw-page-title-main">Cyproconazole</span> Chemical compound

Cyproconazole is an agricultural fungicide of the class of azoles, used on cereal crops, coffee, sugar beet, fruit trees and grapes, and peanuts, on sod farms and golf course turf and on wood as a preservative. It has been used against powdery mildew, rust on cereals and apple scab, and applied by air or on the ground or by chemigation.

References

  1. 1 2 Jeschke, Peter; Witschel, Matthias; Krämer, Wolfgang; Schirmer, Ulrich (25 January 2019). "33.4 Voltage‐dependent Sodium Channel‐blocking Insecticides". Modern Crop Protection Compounds (3rd ed.). Wiley‐VCH. pp. 1424–1448. ISBN   9783527699261.{{cite book}}: CS1 maint: date and year (link)
  2. United States Environmental Protection Agency. Office of Prevention, Pesticides and Toxic Substances (7505C). Pesticide Fact Sheet. Name of Chemical: Indoxacarb. Reason for Issuance: Conditional Registration. Date Issued: October 30, 2000. Archived May 2, 2004, at the Wayback Machine
  3. United States Environmental Protection Agency. Federal Register: Indoxacarb; Pesticide Tolerance. Federal Register: July 11, 2007 (Volume 72, Number 132)
  4. Commission Directive 2006/10/EC of 27 January 2006 amending Council Directive 91/414/EEC to include forchlorfenuron and indoxacarb as active substances. Official Journal of the European Union 2006-1-28
  5. Wang, Kai-Yun; Zhang, Yong; Wang, Hong-Yan; Xia, Xiao-Ming; Liu, Tong-Xian (2010-01-01). "Influence of three diets on susceptibility of selected insecticides and activities of detoxification esterases of Helicoverpa assulta (Lepidoptera: Noctuidae)". Pesticide Biochemistry and Physiology. 96 (1): 51–55. doi:10.1016/j.pestbp.2009.09.003.
  6. "C/2021/8467, Commission Implementing Regulation (EU) 2021/2081 of 26 November 2021 concerning the non-renewal of approval of the active substance indoxacarb, in accordance with Regulation (EC) No 1107/2009 of the European Parliament and of the Council concerning the placing of plant protection products on the market, and amending Commission Implementing Regulation (EU) No 540/2011 (Text with EEA relevance)". 26 November 2021.
  7. "UK authorised biocidal products - Biocides - HSE".
  8. McCann, Stephen F; Annis, Gary D; Shapiro, Rafael; Piotrowski, David W; Lahm, George P; Long, Jeffery K; Lee, Kevin C; Hughes, Margaret M; Myers, Brian J; Griswold, Sandra M; Reeves, Bonita M; March, Robert W; Sharpe, Paula L; Lowder, Patrick; Barnette, William E; Wing, Keith D (2001). "The discovery of indoxacarb: oxadiazines as a new class of pyrazoline-type insecticides". Pest Management Science . 57 (2). Society of Chemical Industry (Wiley): 153–164. doi:10.1002/1526-4998(200102)57:2<153::aid-ps288>3.0.co;2-o. ISSN   1526-498X. PMID   11455646.
  9. McCann, Stephen F.; Annis, Gary D.; Shapiro, Rafael; Piotrowski, David W.; Lahm, George P.; Long, Jeffrey K.; Lee, Kevin C.; Hughes, Margaret M.; Myers, Brian J.; Griswold, Sandra M.; Reeves, Bonita M.; March, Robert W.; Sharpe, Paula L.; Lowder, Patrick; Tseng, Paul; Barnette, William E.; Wing, Keith D. (2001-07-23). "Synthesis and Biological Activity of Oxadiazine and Triazine Insecticides: The Discovery of Indoxacarb". Synthesis and Chemistry of Agrochemicals VI. ACS Symposium Series. Vol. 800. Washington, DC: American Chemical Society. pp. 166–177. doi:10.1021/bk-2002-0800.ch016. ISBN   9780841237834. ISSN   0097-6156.
  10. "Indoxacarb Insecticide Wipes Out Entire Cockroach Generations". June 23, 2008. Archived from the original on June 27, 2008. Retrieved 2009-12-14.
  11. "Syngenta Acquires DuPont Professional Products Insecticide Business". syngenta-us.com.
  12. "Activyl". merck-animal-health-usa.com.
  13. 1 2 Prasanna, Lakshmi; Rao, S. Manimala; Singh, Vishal; Kujur, Rash; Gowrishankar (2008). "Indoxacarb poisoning: An unusual presentation as methemoglobinemia". Indian Journal of Critical Care Medicine. 12 (4): 198–200. doi: 10.4103/0972-5229.45082 . ISSN   0972-5229. PMC   2738321 . PMID   19742262.
  14. Rehman, Habib Ur (September 2001). "Methemoglobinemia". The Western Journal of Medicine. 175 (3): 193–196. doi:10.1136/ewjm.175.3.193. PMC   1071541 . PMID   11527852.
  15. Ludlow, John T.; Wilkerson, Richard G.; Nappe, Thomas M. (2023), "Methemoglobinemia", StatPearls, Treasure Island (FL): StatPearls Publishing, PMID   30726002 , retrieved 2023-09-01

Further reading