Penflufen

Last updated
Penflufen
Penflufen structure.svg
Names
IUPAC name
5-Fluoro-1,3-dimethyl-N-[2-(4-methylpentan-2-yl)phenyl]pyrazole-4-carboxamide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.113.711 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C18H24FN3O/c1-11(2)10-12(3)14-8-6-7-9-15(14)20-18(23)16-13(4)21-22(5)17(16)19/h6-9,11-12H,10H2,1-5H3,(H,20,23) Yes check.svgY
    Key: GOFJDXZZHFNFLV-UHFFFAOYSA-N Yes check.svgY
  • CC1=NN(C(=C1C(=O)NC2=CC=CC=C2C(C)CC(C)C)F)C
Properties
C18H24FN3O
Molar mass 317.408 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Penflufen is a fungicide which was produced and patented by Bayer AG in 2006 and is used for crop protection from fungi. [1] [2] Penflufen is a new generation succinate-dehydrogenase inhibitor, which blocks the electron transport at complex II in the mitochondrial respiration chain. [3] The European Chemical Agency (ECHA) has also approved the use of penflufen as a biocide in wood preservation while labelling it to be a suspected carcinogen. [4]

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">Pesticide resistance</span> Decreased effectiveness of a pesticide on a pest

Pesticide resistance describes the decreased susceptibility of a pest population to a pesticide that was previously effective at controlling the pest. Pest species evolve pesticide resistance via natural selection: the most resistant specimens survive and pass on their acquired heritable changes traits to their offspring. If a pest has resistance then that will reduce the pesticide's efficacy – efficacy and resistance are inversely related.

A biocide is defined in the European legislation as a chemical substance or microorganism intended to destroy, deter, render harmless, or exert a controlling effect on any harmful organism. The US Environmental Protection Agency (EPA) uses a slightly different definition for biocides as "a diverse group of poisonous substances including preservatives, insecticides, disinfectants, and pesticides used for the control of organisms that are harmful to human or animal health or that cause damage to natural or manufactured products". When compared, the two definitions roughly imply the same, although the US EPA definition includes plant protection products and some veterinary medicines.

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<span class="mw-page-title-main">Powdery mildew</span> Fungal plant disease

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<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.

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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">Epoxiconazole</span> Fungicide

Epoxiconazole is a fungicide active ingredient from the class of azoles developed to protect crops. In particular, the substance inhibits the metabolism of fungi cells infesting useful plants, and thereby prevents the growth of the mycelia. Epoxiconazole also limits the production of conidia (mitospores). Epoxiconazole was introduced to the market by BASF SE in 1993 and can be found in many products and product mixtures targeting a large number of pathogens in various crops. Crops are, for example, cereals, soybeans, banana, rice, coffee, turnips, and red as well as sugar beets.

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

Mepronil is a fungicide used as a seed treatment or foliar spray in agriculture to protect crops from fungal diseases. It was first marketed by Kumiai Chemical Industries in 1981 using their brand name Basitac. The compound is a benzanilide which combines 2-methylbenzoic acid with the O-isopropyl derivative of 3-aminophenol to give an inhibitor of succinate dehydrogenase (SDHI).

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Leptospermone is a chemical compound produced by some members of the myrtle family (Myrtaceae), such as Callistemon citrinus, a shrub native to Australia, and Leptospermum scoparium (Manuka), a New Zealand tree from which it gets its name. Modification of this allelopathic chemical to produce mesotrione led to the commercialization of derivative compounds as HPPD inhibitor herbicides.

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

Dazomet is a common soil fumigant that acts as a herbicide, fungicide, slimicide, and nematicide.

Trunk injection or endotherapy also known as vegetative endotherapy, is a method of target-precise application of pesticides, plant resistance activators, or fertilizers into the xylem vascular tissue of a tree with the purpose of protecting the tree from pests, or to inject nutrients to correct for nutrient deficiencies. This method largely relies on harnessing the tree's vascular system to translocate and distribute the active compounds into the wood, canopy and roots where protection or nutrition is needed.

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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.

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

Fludioxonil is a synthetic phenylpyrrole chemical introduced by Ciba-Geigy in 1993 for use as a non-systemic fungicide. It is a structural analog of the natural fungicide pyrrolnitrin.

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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.

<span class="mw-page-title-main">Agriculture in California</span> Sector of the Californian economy

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<span class="mw-page-title-main">Strawberry cultivation in California</span>

Strawberries in the United States are almost entirely grown in California – 86% of fresh and 98% of frozen in 2017 – with Florida a distant second. Of that 30.0% was from Monterey, 28.6% from Ventura, 20.0% from Santa Barbara, 10.0% from San Luis Obispo, and 9.2% from Santa Cruz. The Watsonville/Salinas strawberry zone in Santa Cruz/Monterey, and the Oxnard zone in Ventura, contribute heavily to those concentrations.

<span class="mw-page-title-main">Pydiflumetofen</span> Chemical fungicide

Pydiflumetofen is a broad spectrum fungicide used in agriculture to protect crops from fungal diseases. It was first marketed by Syngenta in 2016 using their brand name Miravis. The compound is an amide which combines a pyrazole acid with a substituted phenethylamine to give an inhibitor of succinate dehydrogenase, an enzyme that inhibits cellular respiration in almost all living organisms.

References

  1. Tian, Fajun; Liu, Xingang; Wu, Yanbing; Xu, Jun; Dong, Fengshou; Wu, Xiaohu; Zheng, Yongquan (December 2016). "Simultaneous determination of penflufen and one metabolite in vegetables and cereals using a modified quick, easy, cheap, effective, rugged, and safe method and liquid chromatography coupled to tandem mass spectrometry". Food Chemistry. 213: 410–416. doi:10.1016/j.foodchem.2016.06.117. ISSN   0308-8146. PMID   27451198.
  2. Russell, Phil (2004-06-01). "14th. International Reinhardsbrunn Symposium, Modern Fungicides and Antifungal Compounds, April 25–29 2004, Friedrichroda, Germany". Outlooks on Pest Management. 15 (3): 115–117. doi:10.1564/15jun09. ISSN   1743-1026.
  3. Dewar, Alan M. (2012-06-01). "Crop Protection in Northern Britain: A Review of the Recent Dundee Conference". Outlooks on Pest Management. 23 (3): 100–101. doi:10.1564/23jun02. ISSN   1743-1026.
  4. ECHA. "ECHA substance info card on Penflufen" . Retrieved October 18, 2024.