Chlorpropham

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Chlorpropham

Chlorpropham
Names

IUPAC name
Isopropyl (3-chlorophenyl)carbamate

Other names
Chlorpropham

Identifiers

CAS Number


  • 101-21-3


3D model (JSmol)


  • Interactive image


ChEBI


  • CHEBI:34630 ☑Y


ChemSpider

  • 2627


ECHA InfoCard

100.002.660

EC Number
202-567-1

KEGG

  • C14506



PubChem CID


  • 2728


UNII


  • 0HBU04R8B0 ☑Y





Properties

Chemical formula


C10H12ClNO2

Molar mass

7002213660000000000♠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).


Infobox references


Chlorpropham (commercial names: Bud Nip, Taterpex, Preventol, Elbanil, Metoxon, Nexoval, Stickman Pistols, Preweed, Furloe, Stopgerme-S, Sprout Nip, Mirvale, Bygran, ChlorIPC, CHLOROPROPHAM, Spud-Nic, Spud-Nie, Chloro-IFK, Chloro-IPC, Keim-stop, Triherbicide 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 within the maximum residue limit regulation in Germany germination inhibitors approved for the treatment of potatoes for the purpose of preservation after harvest. Chlorpropham products are approved as a germination inhibitor for potatoes in Germany, Austria and Switzerland. Chlorpropham is approved for use as a plant regulator and herbicide only on potatoes in the United States.[1]




Contents





  • 1 Toxicity


  • 2 Stability


  • 3 References


  • 4 External links




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 carginogenic risk, chlorpropham is classified by the EPA as group E (non-carcinogenic).[2] One of its metabolites is 3-chloroaniline.


The acceptable daily intake ranges from 0.03 mg/kg (FAO 2001[3]) to 0.05 mg/Kg (EPA 1996[2] and EC 2003[4]).



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).[4]


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.[5] 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.



References




  1. ^ http://www.ecfr.gov/cgi-bin/text-idx?SID=211601858f4f236cff4d417b617de968&mc=true&node=se40.24.180_1181&rgn=div8


  2. ^ ab "Registration Eligibility Decision (Chlorpropham)". Registration Eligibility Decision (Chlorpropham) (PDF). Environmental Pretection Agency. 1996..mw-parser-output cite.citationfont-style:inherit.mw-parser-output .citation qquotes:"""""""'""'".mw-parser-output .citation .cs1-lock-free abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .citation .cs1-lock-limited a,.mw-parser-output .citation .cs1-lock-registration abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .citation .cs1-lock-subscription abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registrationcolor:#555.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration spanborder-bottom:1px dotted;cursor:help.mw-parser-output .cs1-ws-icon abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Wikisource-logo.svg/12px-Wikisource-logo.svg.png")no-repeat;background-position:right .1em center.mw-parser-output code.cs1-codecolor:inherit;background:inherit;border:inherit;padding:inherit.mw-parser-output .cs1-hidden-errordisplay:none;font-size:100%.mw-parser-output .cs1-visible-errorfont-size:100%.mw-parser-output .cs1-maintdisplay:none;color:#33aa33;margin-left:0.3em.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-formatfont-size:95%.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-leftpadding-left:0.2em.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-rightpadding-right:0.2em


  3. ^ "Clorpropham: Toxicological evaluation". Pesticide Residues in Food, 2000. Food and Agriculture Organization. 2001. pp. 41–4. ISBN 978-92-5-104547-3.


  4. ^ ab HEALTH & CONSUMER PROTECTION DIRECTORATE-GENERAL. chlorpropham (PDF). European commission.


  5. ^ 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.




External links


  • US NIST Chemistry WebBook Entry

  • Toxicology Info Cornell University


  • 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.


  • "Clorpropham: Toxicological evaluation". Pesticide Residues in Food, 2000. Food and Agriculture Organization. 2001. pp. 41–4. ISBN 978-92-5-104547-3.


  • "Chlorpropham: Human Health Effects". Hazardous Substances Data Bank.


  • David, B.; Lhote, M.; Faure, V.; Boule, P. (1998). "Ultrasonic and photochemical degradation of chlorpropham and 3-chloroaniline in aqueous solution". Water Research. 32 (8): 2451. doi:10.1016/S0043-1354(97)00477-6.


  • Wolfe, N; Zepp, R; Paris, D (1978). "Carbaryl, propham and chlorpropham: A comparison of the rates of hydrolysis and photolysis with the rate of biolysis". Water Research. 12 (8): 565. doi:10.1016/0043-1354(78)90134-3.


  • Wolf, D. C.; Martin, J. P. (1976). "decomposessition of Fungal Mycelia and Humic-type Polymers Containing Carbon-14 from Ring and Side-chain Labeled 2,4-D and Chlorpropham1". Soil Science Society of America Journal. 40 (5): 700. doi:10.2136/sssaj1976.03615995004000050028x.

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