Tioxazafen

Last updated
Tioxazafen
Tioxazafen.png
Names
Preferred IUPAC name
3-Phenyl-5-(2-thienyl)-1,2,4-oxadiazole
Other names
MON-102100
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
  • InChI=1S/C12H8N2OS/c1-2-5-9(6-3-1)11-13-12(15-14-11)10-7-4-8-16-10/h1-8H/h3-7,18-19H,1,8H2,2H3
    Key: IHNSIFFSNUQGQN-UHFFFAOYSA-N
  • O1N=C(N=C1C=2SC=CC2)C3=CC=CC=C3
Properties
C12H8N2OS
Molar mass 228.27 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN (what is  Yes check.svgYX mark.svgN ?)

Tioxazafen [ISO] is a seed treatment nematicide developed by Monsanto to provide consistent broad-spectrum control of nematodes in corn, soy, and cotton. Its structure has a disubstituted oxadiazole skeleton, representing a new class of nematicides. Greenhouse and field trials suggest that it is at least as effective as existing commercial nematicides for the control of soybean cyst nematode, root-knot nematode, and reniform nematode. [1]

Tioxazafen is marketed commercially as Nemastrike. [2]

Related Research Articles

A nematicide is a type of chemical pesticide used to kill plant-parasitic nematodes. Nematicides have tended to be broad-spectrum toxicants possessing high volatility or other properties promoting migration through the soil. Aldicarb (Temik), a carbamate insecticide marketed by Bayer CropScience, is an example of a commonly used commercial nematicide. It is important in potato production, where it has been used for control of soil-borne nematodes. Aldicarb is a cholinesterase inhibitor, which prevents the breakdown of acetylcholine in the synapse. In case of severe poisoning, the victim dies of respiratory failure. It is no longer authorised for use in the EU and, in August 2010, Bayer CropScience announced that it planned to discontinue aldicarb by 2014. Human health safety and environmental concerns have resulted in the widespread deregistration of several other agronomically important nematicides. Prior to 1985, the persistent halocarbon DBCP was a widely used nematicide and soil fumigant. However, it was banned from use after being linked to sterility among male workers; the Dow Chemical company was subsequently found liable for more than $600 million in damages.

Chloropicrin, also known as PS and nitrochloroform, is a chemical compound currently used as a broad-spectrum antimicrobial, fungicide, herbicide, insecticide, and nematicide. It was used as a poison gas in World War I. Its chemical structural formula is Cl3CNO2.

<span class="mw-page-title-main">Spraing</span> Disease of potatoes

Spraing is a collective term for diseases and disorders of potato tubers that cause brown streaks in the flesh of the potato. Spraing can be caused by two viruses, tobacco rattle virus (TRV) which is transmitted by trichodorid nematodes, or Potato mop-top virus (PMTV) transmitted by the powdery scab fungus Spongospora subterranea. The two viruses may have synergistic effects in disease progression when both are present. Spraing like symptoms can also be caused by physiological defects or specific nutrient deficiencies, most notably Calcium.

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

Iprodione is a hydantoin fungicide and nematicide.

Antiparasitics are a class of medications which are indicated for the treatment of parasitic diseases, such as those caused by helminths, amoeba, ectoparasites, parasitic fungi, and protozoa, among others. Antiparasitics target the parasitic agents of the infections by destroying them or inhibiting their growth; they are usually effective against a limited number of parasites within a particular class. Antiparasitics are one of the antimicrobial drugs which include antibiotics that target bacteria, and antifungals that target fungi. They may be administered orally, intravenously or topically. Overuse or misuse of antiparasitics can lead to the development of antimicrobial resistance.

Devgen is a Belgium-based multinational agricultural biotechnology company. It uses biotechnology and molecular breeding technologies to develop varieties of food crops. Its technology is marketed by outlicensing or selling seeds in India and South-East Asia. Devgen also develops nematicides.

<i>Meloidogyne javanica</i> Species of roundworm

Meloidogyne javanica is a species of plant-pathogenic nematodes. It is one of the tropical root-knot nematodes and a major agricultural pest in many countries. It has many hosts. Meloidogyne javanica reproduces by obligatory mitotic parthenogenesis (apomixis).

Pratylenchus brachyurus is a plant parasitic nematode.

<i>Ditylenchus dipsaci</i> Species of flowering plant

Ditylenchus dipsaci is a plant pathogenic nematode that primarily infects onion and garlic. It is commonly known as the stem nematode, the stem and bulb eelworm, or onion bloat. Symptoms of infection include stunted growth, discoloration of bulbs, and swollen stems. D. dipsaci is a migratory endoparasite that has a five-stage lifecycle and the ability to enter into a dormancy stage. D. dipsaci enters through stomata or plant wounds and creates galls or malformations in plant growth. This allows for the entrance of secondary pathogens such as fungi and bacteria. Management of disease is maintained through seed sanitation, heat treatment, crop rotation, and fumigation of fields. D. dipsaci is economically detrimental because infected crops are unmarketable.

Helicotylenchus multicinctus is a plant pathogenic nematode that affects primarily bananas and plantains. Nematodes of the genus Helicotylenchus are spiral nematodes and feed on a large variety of plant species.

Xiphinema americanum, the American dagger nematode, is a species of plant pathogenic nematodes. It is one of many species that belongs to the genus Xiphinema. It was first described by N. A. Cobb in 1913, who found it on both sides of the United States on the roots of grass, corn, and citrus trees. Not only is Xiphinema americanum known to vector plant viruses, but also X. americanum has been referred to as "the most destructive plant parasitic nematode in America", and one of the four major nematode pests in the Southeastern United States.

Xiphinema diversicaudatum is an amphimictic ectoparasitic nematode species. This species has a characteristically long stylet capable of penetrating into a host's vascular tissue. They have a wide host range with some of the extensively studied ones being strawberry, hops and raspberry, due to their economic importance. The direct root damage caused through penetration near the root tip and formation of galls is a secondary concern when compared with the damage caused by vectoring the Arabis mosaic virus. The virus attaches to the interior cuticle lining and can be transferred from infected to uninfected root tissue as the nematode feeds and sheds. Management of this particular nematode relies on nematicides such as 1,3-Dichloropropene (Telone) at 40 gpa.or methyl bromide at 1000 lb/ac to control to 28 in deep.

Mesocriconema xenoplax is a species of plant parasitic nematodes. Nematodes of this particular species are collectively called ring nematodes.

<span class="mw-page-title-main">Nematology</span> Scientific study of roundworms

Nematology is the scientific discipline concerned with the study of nematodes, or roundworms. Although nematological investigation dates back to the days of Aristotle or even earlier, nematology as an independent discipline has its recognizable beginnings in the mid to late 19th century.

<i>Pratylenchus</i> Genus of roundworms

Pratylenchus is a genus of nematodes known commonly as lesion nematodes. They are parasitic on plants and are responsible for root lesion disease on many taxa of host plants in temperate regions around the world. Lesion nematodes are migratory endoparasites that feed and reproduce in the root and move around, unlike the cyst or root-knot nematodes, which may stay in one place. They usually only feed on the cortex of the root. Species are distinguished primarily by the morphology of the stylets.

Strawberry foliar nematode, or strawberry crimp nematode, is a disease caused by Aphelenchoides fragariae, a plant pathogenic nematode. It is common in strawberries and ornamental plants and can greatly affect plant yield and appearance, resulting in a loss of millions of dollars of revenue. Symptoms used to diagnose the disease are angular, water soaked lesions and necrotic blotches. Aphelenchoides fragariae is the nematode pathogen that causes the disease. Its biological cycle includes four life stages, three of which are juvenile. The nematode can undergo multiple life cycles in one growing season when favorable conditions are present. The crowns, runners, foliage, and new buds of the plant via stylet penetration or through the stomata can be infected. The best management practices for this disease are sanitation, prevention of induction of the pathogen to the environment, and planting clean seed or starter plants.

<span class="mw-page-title-main">SmartStax</span> Seeds protected against bugs, weeds

SmartStax is a brand of genetically modified seed made through a collaboration between Monsanto Company and Dow Chemical Company. It takes advantage of multiple modes of insect protection and herbicide tolerance. SmartStax takes advantage of Yieldgard VT Triple (Monsanto), Herculex Xtra (Dow), RoundUp Ready 2 (Monsanto), and Liberty Link (Dow). The traits included protect against above-ground insects, below-ground insects, and provide broad herbicide tolerance. It is currently available for corn, but cotton, soybean, and specialty crop variations are to be released. Previously, the most genes artificially added to a single plant was three, but Smartstax includes eight. Smartstax also incorporates Monsanto's Acceleron Seed Treatment System which protects against insects at the earliest stages of development. Smartstax is sold under the Genuity (Monsanto) and Mycogen (Dow) brands.

Pratylenchus alleni is a migratory endoparasitic nematode, living inside of plant roots and feeding on parenchyma cells in the root cortex. P. alleni is an obligate biotroph, meaning it must have a living host in order to survive. Due to their incredibly broad host range, Pratylenchus species fall third in total economic impact, finishing just behind cyst nematodes and root knot nematodes (Meloidogyne). In Canada, it was isolated for the first time in 2011 in a soybean field.

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

Sedaxane is a broad spectrum fungicide used as a seed treatment in agriculture to protect crops from fungal diseases. It was first marketed by Syngenta in 2011 using their brand name Vibrance. The compound is an amide which combines a pyrazole acid with an aryl amine to give an inhibitor of succinate dehydrogenase.

Scutellonema bradys, also known as yam nematode, is a migratory endoparasitic nematode causing major damage to yam crop in many African tropical regions, as well in parts of South and Central America and Asia. They can cause reduction of 20-30% in tuber weight at harvest.

References

  1. Slomczynska, Urszula; South, Michael S.; Bunkers, Greg J.; Edgecomb, Donald; Wyse-Pester, Dawn; Selness, Shaun; Ding, Yiwei; Christiansen, Jessica; Ediger, Kent; Miller, William; Charumilind, Pana; Hartmann, Gregory; Williams, Jeremy; Dimmic, Matthew; Shortt, Barry; Haakenson, William; Wideman, Al; Crawford, Michael; Hresko, Michelle; McCarter, James (2015). "Tioxazafen: A New Broad-Spectrum Seed Treatment Nematicide". Discovery and Synthesis of Crop Protection Products. ACS Symposium Series. Vol. 1204. pp. 129–147. doi:10.1021/bk-2015-1204.ch010. ISBN   978-0-8412-3102-3.
  2. "Corn Grower Tests New Nematode Seed Treatment NemaStrike". Successful Farming. 27 August 2018.