Dichlone

Last updated
Dichlone
2,3-dichloronaphthalene-1,4-dione 200.svg
Names
Preferred IUPAC name
2,3-Dichloronaphthalene-1,4-dione
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.003.828 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 204-210-5
PubChem CID
UNII
UN number 2902 2761
  • InChI=1S/C10H4Cl2O2/c11-7-8(12)10(14)6-4-2-1-3-5(6)9(7)13/h1-4H
    Key: SVPKNMBRVBMTLB-UHFFFAOYSA-N
  • C1=CC=C2C(=C1)C(=O)C(=C(C2=O)Cl)Cl
Properties
C10H4Cl2O2
Molar mass 227.04 g·mol−1
AppearanceYellow crystals [1]
Melting point 193 °C (379 °F; 466 K) [1]
0.1 ppm [1]
Hazards
GHS labelling:
GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
Warning
H302, H315, H317, H319, H410
P261, P264, P264+P265, P270, P272, P273, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Dichlone (trade names Phygon and Quintar) is a fungicide and algicide of the quinone class. It is a general use fungicide applied to fruits, vegetables, field crops, ornamentals, and residential and commercial outdoor areas. [1] It is also used to control blue algae. [2]

Dichlone is not persistent in soil and has moderate mammalian toxicity. [2]

Dichlone can be manufactured by the chlorination and oxidation of naphthalene. [3]

Synthesis of dichlone from naphthalene Synthesis of Dichlone.svg
Synthesis of dichlone from naphthalene

Related Research Articles

Restricted use pesticides (RUP) are pesticides not available to the general public in the United States. Fulfilling its pesticide regulation responsibilities, the United States Environmental Protection Agency (EPA) registers all pesticides as either "unclassified" or "restricted use". Unclassified pesticides are available over-the-counter, while the latter require a license to purchase and apply the product. Pesticides are classified as "restricted use" for a variety of reasons, such as potential for or history of groundwater contamination.

Fungicides are pesticides used to kill parasitic fungi or their spores. Fungi can cause serious damage in agriculture, resulting in losses of yield and quality. Fungicides are used both in agriculture and to fight fungal infections in animals. Fungicides are also used to control oomycetes, which are not taxonomically/genetically fungi, although sharing similar methods of infecting plants. Fungicides can either be contact, translaminar or systemic. Contact fungicides are not taken up into the plant tissue and protect only the plant where the spray is deposited. Translaminar fungicides redistribute the fungicide from the upper, sprayed leaf surface to the lower, unsprayed surface. Systemic fungicides are taken up and redistributed through the xylem vessels. Few fungicides move to all parts of a plant. Some are locally systemic, and some move upward.

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

Carbendazim is a fungicide, a member benzimidazole fungicides. It is a metabolite of benomyl.

<span class="mw-page-title-main">Federal Insecticide, Fungicide, and Rodenticide Act</span> US federal law governing pesticide regulation

The Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA) is a United States federal law that set up the basic U.S. system of pesticide regulation to protect applicators, consumers, and the environment. It is administered and regulated by the United States Environmental Protection Agency (EPA) and the appropriate environmental agencies of the respective states. FIFRA has undergone several important amendments since its inception. A significant revision in 1972 by the Federal Environmental Pesticide Control Act (FEPCA) and several others have expanded EPA's present authority to oversee the sales and use of pesticides with emphasis on the preservation of human health and protection of the environment by "(1) strengthening the registration process by shifting the burden of proof to the chemical manufacturer, (2) enforcing compliance against banned and unregistered products, and (3) promulgating the regulatory framework missing from the original law".

<span class="mw-page-title-main">Vinclozolin</span> Fungicide used on fruits and vegetables

Vinclozolin is a common dicarboximide fungicide used to control diseases, such as blights, rots and molds in vineyards, and on fruits and vegetables such as raspberries, lettuce, kiwi, snap beans, and onions. It is also used on turf on golf courses. Two common fungi that vinclozolin is used to protect crops against are Botrytis cinerea and Sclerotinia sclerotiorum. First registered in 1981, vinclozolin is widely used but its overall application has declined. As a pesticide, vinclozolin is regulated by the United States Environmental Protection Agency. In addition to these restrictions within the United States, as of 2006 the use of this pesticide was banned in several countries, including Denmark, Finland, Norway, and Sweden. It has gone through a series of tests and regulations in order to evaluate the risks and hazards to the environment and animals. Among the research, a main finding is that vinclozolin has been shown to be an endocrine disruptor with antiandrogenic effects.

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

Captan is a general use pesticide (GUP) that belongs to the phthalimide class of fungicides. It is a white solid, although commercial samples appear yellow or brownish.

<span class="mw-page-title-main">Chlorothalonil</span> Fungicide

Chlorothalonil (2,4,5,6-tetrachloroisophthalonitrile) is an organic compound mainly used as a broad spectrum, nonsystemic fungicide, with other uses as a wood protectant, pesticide, acaricide, and to control mold, mildew, bacteria, algae. Chlorothalonil-containing products are sold under the names Bravo, Echo, and Daconil. It was first registered for use in the US in 1966. In 1997, it was the third most used fungicide in the US, behind only sulfur and copper, with 12 million pounds used in agriculture that year. Including nonagricultural uses, the United States Environmental Protection Agency (EPA) estimates, on average, almost 15 million lb (6.8 million kg) were used annually from 1990 to 1996.

<span class="mw-page-title-main">Algaecide</span>

Algaecide or algicide is a biocide used for killing and preventing the growth of algae, often defined in a loose sense that, beyond the biological definition, also includes cyanobacteria. An algaecide may be used for controlled bodies of water, but may also be used on land for locations such as turfgrass.

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">Procymidone</span> Chemical compound

Procymidone is a pesticide. It is often used for killing unwanted ferns and nettles, and as a dicarboximide fungicide for killing fungi, for example as seed dressing, pre-harvest spray or post-harvest dip of lupins, grapes, stone fruit, strawberries. It is a known endocrine disruptor which interferes with the sexual differentiation of male rats. It is considered to be a poison.

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

Metam sodium is an organosulfur compound with the formula CH3NHCS2Na. The compound is a sodium salt of a dithiocarbamate. The compound exists as a colorless dihydrate, but most commonly it is encountered as an aqueous solution. It is used as a soil fumigant, pesticide, herbicide, and fungicide. It is one of the most widely used pesticides in the United States, with approximately 60 million pounds used in 2001.

Zineb is the chemical compound with the formula {Zn[S2CN(H)CH2CH2N(H)CS2]}n. Structurally, it is classified as a coordination polymer and a dithiocarbamate complex. This pale yellow solid is used as fungicide.

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

Enilconazole is a fungicide widely used in agriculture, particularly in the growing of citrus fruits. Trade names include Freshgard, Fungaflor, and Nuzone.

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

Thiram is the simplest thiuram disulfide and the oxidized dimer of dimethyldithiocarbamate. It is used as a fungicide, ectoparasiticide to prevent fungal diseases in seed and crops and similarly as an animal repellent to protect fruit trees and ornamentals from damage by rabbits, rodents and deer. It is effective against Stem gall of coriander, damping off, smut of millet, neck rot of onion, etc. Thiram has been used in the treatment of human scabies, as a sun screen and as a bactericide applied directly to the skin or incorporated into soap.

This is an index of articles relating to pesticides.

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

Propamocarb is a systemic fungicide used for control of soil, root and leaf disease caused by oomycetes. It is used by watering or spraying. Propamocarb is absorbed and distributed through the plant's tissue.

<span class="mw-page-title-main">Zinc bis(dimethyldithiocarbamate)</span> Chemical compound

Zinc dimethyldithiocarbamate is a coordination complex of zinc with dimethyldithiocarbamate. It is a pale yellow solid that is used as a fungicide, the sulfur vulcanization of rubber, and other industrial applications.

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

Prochloraz, brand name Sportak, is an imidazole fungicide that was introduced in 1978 and is widely used in Europe, Australia, Asia, and South America within gardening and agriculture to control the growth of fungi. It is not registered for use in the United States. Similarly to other azole fungicides, prochloraz is an inhibitor of the enzyme lanosterol 14α-demethylase (CYP51A1), which is necessary for the production of ergosterol – an essential component of the fungal cell membrane – from lanosterol. The agent is a broad-spectrum, protective and curative fungicide, effective against Alternaria spp., Botrytis spp., Erysiphe spp., Helminthosporium spp., Fusarium spp., Pseudocerosporella spp., Pyrenophora spp., Rhynchosporium spp., and Septoria spp.

References

  1. 1 2 3 4 "Dichlone (Phygon, Quintar) Chemical Profile". Pesticide Management Education Program, Cornell Cooperative Extension.
  2. 1 2 "Dichlone". Pesticide Properties DataBase, University of Hertfordshire.
  3. Thomas A. Unger (1996). Pesticide Synthesis Handbook. William Andrew. p. 966. ISBN   0-8155-1853-6.