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Preferred IUPAC name Propan-2-yl (3-chlorophenyl)carbamate | |
Other names Chlorpropham, CIPC, isopropyl N-(3-chlorophenyl) carbamate | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.002.660 |
EC Number |
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KEGG | |
PubChem CID | |
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CompTox Dashboard (EPA) | |
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Properties | |
C10H12ClNO2 | |
Molar mass | 213.66 g·mol−1 |
Appearance | Beige to brown solid |
Density | 1.18 g/cm3 |
Melting point | 41 to 42 °C (106 to 108 °F; 314 to 315 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Chlorpropham or CIPC is a plant growth regulator and herbicide used as a sprout suppressant for grass weeds, alfalfa, lima and snap beans, blueberries, cane fruit, carrots, cranberries, ladino clover, garlic, seed grass, onions, spinach, sugar beets, tomatoes, safflower, soybeans, gladioli and woody nursery stock. It is also used to inhibit potato sprouting and for sucker control in tobacco. Chlorpropham is available in emulsifiable concentrate and liquid formulations.
Chlorpropham is approved for use as a plant regulator and herbicide only on potatoes in the United States. [1] The use of CIPC was banned in the EU and UK in 2019 after it was not reauthorised for use due to toxicity concerns, with sales prohibited from January 2020. [2]
When it is used as an anti-sprouting agent for potatoes, the formulation is based on HN formulation, Hot Fogging. [3]
Commercial names include Bud Nip, Taterpex, Preventol, Elbanil, Metoxon, Nexoval, Stickman Pistols, Preweed, Furloe, Stopgerme-S, Sprout Nip, Mirvale, Bygran, ChlorIPC, Spud-Nic, Spud-Nie, Chloro-IFK, Chloro-IPC, Keim-stop, Triherbicide CIPC, OORJA. For herbicide, an EC formulation is used so that it is dissolvable in water for spray in the field. [4]
Chlorpropham displays a low level toxicity profile, with no signs of acute toxicity after exposure of less than 1000 mg/kg/day. Long term exposure at high doses (≥ 1000 mg/kg/day) could cause reduction of body weight gain, decrease in hematocrit and hemoglobin, and increase in blood reticulocytes.
Regarding the carcinogenic risk, chlorpropham is classified by the EPA as group E (non-carcinogenic). [5] One of its metabolites is 3-chloroaniline.
The acceptable daily intake ranges from 0.03 mg/kg (FAO 2001 [6] ) to 0.05 mg/Kg (EPA 1996 [5] and EC 2003 [7] ).
Chlorpropham is partially degraded in the environment under aerobic conditions (15% to 30% after 100 days) and partially hydrolysed in water solution (90% after 59 to 130 days). [7]
A study of the stability of chlorpropham in potatoes (estimated concentration of chlorpropham: 1.8 to 7.6 mg/kg at 10 days post-application) revealed that mean concentration of chlorpropham in the tuber decreased spontaneously by 24% and 42% at 28 days and 65 days postapplication respectively. [8] The study also showed that peeling removed 91–98% and washing 33–47%. Residues of chlorpropham were detected in the boiled potatoes, in the boiling water, in the French-fried potatoes and in the frying oil. According to this study, the theoretical dose for a 20 kg infant eating 100g of crude-peeled tuber would be 0.00018 to 0.00342 mg/kg.
Roundup is a brand name of herbicide originally produced by Monsanto, which Bayer acquired in 2018. Prior to the late-2010s formulations, it used broad-spectrum glyphosate-based herbicides. As of 2009, sales of Roundup herbicides still represented about 10 percent of Monsanto's revenue despite competition from Chinese producers of other glyphosate-based herbicides. The overall Roundup line of products represented about half of Monsanto's yearly revenue in 2009. The product is marketed to consumers by Scotts Miracle-Gro Company. In the late-2010s other non-glyphosate containing herbicides were also sold under the Roundup brand.
Glyphosate is a broad-spectrum systemic herbicide and crop desiccant. It is an organophosphorus compound, specifically a phosphonate, which acts by inhibiting the plant enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSP). It is used to kill weeds, especially annual broadleaf weeds and grasses that compete with crops. Its herbicidal effectiveness was discovered by Monsanto chemist John E. Franz in 1970. Monsanto brought it to market for agricultural use in 1974 under the trade name Roundup. Monsanto's last commercially relevant United States patent expired in 2000.
Lindane, also known as gamma-hexachlorocyclohexane (γ-HCH), gammaxene, Gammallin and benzene hexachloride (BHC), is an organochlorine chemical and an isomer of hexachlorocyclohexane that has been used both as an agricultural insecticide and as a pharmaceutical treatment for lice and scabies.
Chlorfenvinphos is an organophosphorus compound that was widely used as an insecticide and an acaricide. The molecule itself can be described as an enol ester derived from dichloroacetophenone and diethylphosphonic acid. Chlorfenvinphos has been included in many products since its first use in 1963. However, because of its toxic effect as a cholinesterase inhibitor it has been banned in several countries, including the United States and the European Union. Its use in the United States was discontinued in 1991.
Diethion (C9H22O4P2S4) is an organophosphate insecticide. It is known to affect the neural enzyme acetylcholinesterase and disrupt its function.
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Dinoseb is a common industry name for 6-sec-butyl-2,4-dinitrophenol, a herbicide in the dinitrophenol family. It is a crystalline orange solid which does not readily dissolve in water. Dinoseb is banned as an herbicide in the European Union (EU) and the United States because of its toxicity.
Enilconazole is a fungicide widely used in agriculture, particularly in the growing of citrus fruits. Trade names include Freshgard, Fungaflor, and Nuzone.
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α-Chaconine is a steroidal glycoalkaloid that occurs in plants of the family Solanaceae. It is a natural toxicant produced in green potatoes and gives the potato a bitter taste. Tubers produce this glycoalkaloid in response to stress, providing the plant with insecticidal and fungicidal properties. It belongs to the chemical family of saponins. Since it causes physiological effects on individual organism, chaconine is considered to be defensive allelochemical. Solanine is a related substance that has similar properties.
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Fluopicolide is a fungicide used in agriculture to control diseases caused by oomycetes such as late blight of potato. It is classed as an acylpicolide and its chemical name is 2,6-dichloro-N-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]methyl}benzamide. The precise mode of action is not known, but it is thought to act by affecting spectrin-like proteins in the cytoskeleton of oomycetes. This mode of action differs from other available fungicides used to control oomycetes and it can inhibit the growth of strains that are resistant to phenylamides, strobilurin, dimethomorph and iprovalicarb. It has some systemic activity as it moves through the xylem towards the tips of stems, but does not get transported to the roots. It affects the motility of zoospores, the germination of cysts, the growth of the mycelium and sporulation. Bayer CropScience developed the compound and it was first released as a commercial product in 2006.
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