Chlorpropham

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Chlorpropham
Isopropyl (3-chlorophenyl)carbamate 200.svg
Names
Preferred IUPAC name
Propan-2-yl (3-chlorophenyl)carbamate
Other names
Chlorpropham
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.002.660 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-567-1
KEGG
PubChem CID
UNII
  • InChI=1S/C10H12ClNO2/c1-7(2)14-10(13)12-9-5-3-4-8(11)6-9/h3-7H,1-2H3,(H,12,13)
    Key: CWJSHJJYOPWUGX-UHFFFAOYSA-N
  • InChI=1/C10H12ClNO2/c1-7(2)14-10(13)12-9-5-3-4-8(11)6-9/h3-7H,1-2H3,(H,12,13)
    Key: CWJSHJJYOPWUGX-UHFFFAOYAV
  • CC(C)OC(=O)NC1=CC(=CC=C1)Cl
Properties
C10H12ClNO2
Molar mass 213.66 g·mol−1
AppearanceBeige 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.

Contents

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]

Uses

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]

Toxicity

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] ).

Stability

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.

Related Research Articles

<span class="mw-page-title-main">Potato</span> Staple food, root tuber, starchy

The potato is a starchy root vegetable native to the Americas that is consumed as a staple food in many parts of the world. Potatoes are tubers of the plant Solanum tuberosum, a perennial in the nightshade family Solanaceae.

<span class="mw-page-title-main">Glyphosate</span> Systemic herbicide and crop desiccant

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.

<span class="mw-page-title-main">Lindane</span> Organochlorine chemical and an isomer of hexachlorocyclohexane

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.

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

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 cancelled in 1991.

<span class="mw-page-title-main">Solanine</span> Glycoalkaloid poison found in the nightshade family of plants

Solanine is a glycoalkaloid poison found in species of the nightshade family within the genus Solanum, such as the potato, the tomato, and the eggplant. It can occur naturally in any part of the plant, including the leaves, fruit, and tubers. Solanine has pesticidal properties, and it is one of the plant's natural defenses. Solanine was first isolated in 1820 from the berries of the European black nightshade, after which it was named. It belongs to the chemical family of saponins.

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

Diquat is the ISO common name for an organic dication that, as a salt with counterions such as bromide or chloride is used as a contact herbicide that produces desiccation and defoliation. Diquat is no longer approved for use in the European Union, although its registration in many other countries including the USA is still valid.

<span class="mw-page-title-main">Glufosinate</span> Broad-spectrum herbicide

Glufosinate is a naturally occurring broad-spectrum herbicide produced by several species of Streptomyces soil bacteria. Glufosinate is a non-selective, contact herbicide, with some systemic action. Plants may also metabolize bialaphos and phosalacine, other naturally occurring herbicides, directly into glufosinate. The compound irreversibly inhibits glutamine synthetase, an enzyme necessary for the production of glutamine and for ammonia detoxification, giving it antibacterial, antifungal and herbicidal properties. Application of glufosinate to plants leads to reduced glutamine and elevated ammonia levels in tissues, halting photosynthesis and resulting in plant death.

<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, the most recent year for which data are available, 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">Diphenylamine</span> Chemical compound

Diphenylamine is an organic compound with the formula (C6H5)2NH. The compound is a derivative of aniline, consisting of an amine bound to two phenyl groups. The compound is a colorless solid, but commercial samples are often yellow due to oxidized impurities. Diphenylamine dissolves well in many common organic solvents, and is moderately soluble in water. It is used mainly for its antioxidant properties. Diphenylamine is widely used as an industrial antioxidant, dye mordant and reagent and is also employed in agriculture as a fungicide and antihelmintic.

<span class="mw-page-title-main">Dinoseb</span> Chemical compound used as a herbicide

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.

<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">Monolinuron</span> Chemical compound

Monolinuron is a pesticide, more specifically a selective systemic herbicide and an algaecide. As an herbicide, it is used to control broad-leaved weeds and annual grasses in vegetable crops such as leeks, potatoes, and dwarf French beans. Monolinuron affects the photosynthesis in weeds. Following uptake of monolinuron through roots and leaves of weeds, monolinuron causes early symptoms of yellowing and die-back of the leaves, eventually resulting in weed death. In fishkeeping, it is used to control blanket weed and hair algae.

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

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.

<span class="mw-page-title-main">2,4-Dichlorophenoxyacetic acid</span> Herbicide

2,4-Dichlorophenoxyacetic acid is an organic compound with the chemical formula C8H6Cl2O3 which is usually referred to by its ISO common name 2,4-D. It is a systemic herbicide which kills most broadleaf weeds by causing uncontrolled growth in them but most grasses such as cereals, lawn turf, and grassland are relatively unaffected.

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

Ethoprophos (or ethoprop) is an organophosphate ester with the formula C8H19O2PS2. It is a clear yellow to colourless liquid that has a characteristic mercaptan-like odour. It is used as an insecticide and nematicide and it is an acetylcholinesterase inhibitor.

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

Bentazon is a chemical manufactured by BASF Chemicals for use in herbicides. It is categorized under the thiadiazine group of chemicals. Sodium bentazon is available commercially and appears slightly brown in colour.

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

Novaluron, or (±)-1-[3-chloro-4-(1,1,2-trifluoro-2-trifluoro- methoxyethoxy)phenyl]-3-(2,6-difluorobenzoyl)urea, is a chemical with pesticide properties, belonging to the class of insecticides called insect growth regulators. It is a benzoylphenyl urea developed by Makhteshim-Agan Industries Ltd.. In the United States, the compound has been used on food crops, including apples, potatoes, brassicas, ornamentals, and cotton. Patents and registrations have been approved or are ongoing in several other countries throughout Europe, Asia, Africa, South America, and Australia. The US Environmental Protection Agency and the Canadian Pest Management Regulatory Agency consider novaluron to pose low risk to the environment and non-target organisms and value it as an important option for integrated pest management that should decrease reliance on organophosphorus, carbamate and pyrethroid insecticides.

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

Fluazinam is a broad-spectrum fungicide used in agriculture. It is classed as a diarylamine and more specifically an arylaminopyridine. Its chemical name is 3-chloro-N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5-trifluoromethyl-2-pyridinamine. The mode of action involves the compound being an extremely potent uncoupler of oxidative phosphorylation in mitochondria and also having high reactivity with thiols. It is unique amongst uncouplers in displaying broad-spectrum activity against fungi and also very low toxicity to mammals due to it being rapidly metabolised to a compound without uncoupling activity. It was first described in 1992 and was developed by researchers at the Japanese company Ishihara Sangyo Kaisha.

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

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.

<span class="mw-page-title-main">1,4-Dimethylnaphthalene</span> Chemical compound

1,4-Dimethylnaphthalene (1,4DMN) is a plant growth regulator that occurs naturally in potato tubers, preventing them from sprouting. Synthetic forms such as 1-4SIGHT are applied to potatoes during storage.

References

  1. "§180.181 Chlorpropham". eCFR Code of Federal Regulations. Archived from the original on 2017-06-10. Retrieved 2021-10-07.
  2. Epp, Melanie (2021-04-12). "The Worry with CIPC". EuropeanSeed. Archived from the original on 2021-06-12. Retrieved 12 June 2021.
  3. "Codes for Formulations" (PDF). Archived (PDF) from the original on 2018-04-13. Retrieved 2021-10-07.
  4. "Cleancrop Amigo 2". uk.uplonline.com. Archived from the original on 2019-06-23. Retrieved 2019-06-23.
  5. 1 2 Registration Eligibility Decision (Chlorpropham) (PDF). Environmental Pretection Agency. 1996. Archived (PDF) from the original on 2014-10-16. Retrieved 2014-03-25.
  6. "Clorpropham: Toxicological evaluation". Pesticide Residues in Food, 2000. Food and Agriculture Organization. 2001. pp. 41–4. ISBN   978-92-5-104547-3. Archived from the original on 2014-06-17. Retrieved 2021-10-07.
  7. 1 2 HEALTH & CONSUMER PROTECTION DIRECTORATE-GENERAL. chlorpropham (PDF). European commission. Archived (PDF) from the original on 2014-04-21. Retrieved 2014-03-25.
  8. Lentza-Rizos, Chaido; Balokas, Alfaios (2001). "Residue Levels of Chlorpropham in Individual Tubers and Composite Samples of Postharvest-Treated Potatoes". Journal of Agricultural and Food Chemistry. 49 (2): 710–4. doi:10.1021/jf000018t. PMID   11262017.