Picloram

Last updated
Picloram
Picloram.png
Picloram-3D-spacefill.png
Names
Preferred IUPAC name
4-Amino-3,5,6-trichloropyridine-2-carboxylic acid
Other names
Picloram
Tordon
Grazon
Identifiers
3D model (JSmol)
AbbreviationsATCP
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.016.034 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C6H3Cl3N2O2/c7-1-3(10)2(8)5(9)11-4(1)6(12)13/h(H2,10,11)(H,12,13) Yes check.svgY
    Key: NQQVFXUMIDALNH-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C6H3Cl3N2O2/c7-1-3(10)2(8)5(9)11-4(1)6(12)13/h(H2,10,11)(H,12,13)
    Key: NQQVFXUMIDALNH-UHFFFAOYAR
  • Nc1c(Cl)c(Cl)nc(C(=O)O)c1Cl
Properties
C6H3Cl3N2O2
Molar mass 241.45 g·mol−1
Appearancecolorless to white crystalline solid [1]
Odor chlorine-like [1]
Melting point 218.5 °C (425.3 °F; 491.6 K)decomposes
0.04% (20°C) [1] 430 mg/L at 25 deg C [2]
Vapor pressure 0.0000006 mmHg (35°C) [1]
Hazards
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 15 mg/m3 (total) TWA 5 mg/m3 (resp) [1]
REL (Recommended)
none established [1]
IDLH (Immediate danger)
N.D. [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)
Infobox references

Picloram is a systemic herbicide used for general woody plant control. It also controls a wide range of broad-leaved weeds, but most grasses are resistant. [3] A chlorinated derivative of picolinic acid, picloram is in the pyridine family of herbicides.

Contents

Picloram can be sprayed on foliage, injected into plants, applied to cut surfaces, or placed at the base of the plant where it will leach to the roots. Once absorbed by the foliage, stem, or roots, picloram is transported throughout the plant.

Herbicides containing picloram are sold under a variety of brand names. Dow Chemicals and now Dow AgroSciences sell herbicides containing it under the brand name Tordon. [4]

During the Vietnam War, picloram and other herbicides were combined to make Agent White (commercially available as Tordon 101) and enhanced Agent Orange, which was previously conducted by the British military during the Malayan Emergency. Large quantities of these herbicides were sprayed by U.S. forces in areas where they considered its long-term persistence desirable, such as inland forests. [5]

Safety

Picloram is of moderate toxicity to the eyes and only mildly toxic on the skin. [3] No history of human intoxication by picloram has been documented, so symptoms of acute exposure are difficult to characterize.

Picloram is the most persistent of its family of herbicides. [6] It does not adhere to soil, so may leach to groundwater, and has in fact been detected there. It is degraded in soil and water mainly by microbes. Picloram has very little tendency to accumulate in aquatic life.

Gardeners who use dung as fertilizer should check to make certain that the animal source has not grazed on picloram-treated hay, as the dung still has broadleaf-killing potency. [7]

In regards to occupational exposures, the U. S. Occupational Safety and Health Administration has established a permissible exposure limit of 15 mg/m3 total exposure and 5 mg/m3 for respiratory exposure, over an eight-hour workshift. [8]

Related Research Articles

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Pentachlorophenol Chemical compound

Pentachlorophenol (PCP) is an organochlorine compound used as a pesticide and a disinfectant. First produced in the 1930s, it is marketed under many trade names. It can be found as pure PCP, or as the sodium salt of PCP, the latter of which dissolves easily in water. It can be biodegraded by some bacteria, including Sphingobium chlorophenolicum.

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Benomyl Chemical compound

Benomyl is a fungicide introduced in 1968 by DuPont. It is a systemic benzimidazole fungicide that is selectively toxic to microorganisms and invertebrates, especially earthworms, but nontoxic toward mammals.

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Chlorobenzene is an aromatic organic compound with the chemical formula C6H5Cl. This colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture of other chemicals.

Heptachlor Chemical compound

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2,4,5-Trichlorophenoxyacetic acid Chemical compound

2,4,5-Trichlorophenoxyacetic acid, a synthetic auxin, is a chlorophenoxy acetic acid herbicide used to defoliate broad-leafed plants. It was developed in the late 1940s and was widely used in the agricultural industry until being phased out, starting in the late 1970s due to toxicity concerns. Agent Orange, a defoliant used by the British in the Malayan Emergency and the U.S. in the Vietnam War, was equal parts 2,4,5-T and 2,4-D. 2,4,5-T itself is toxic with a NOAEL of 3 mg/kg/day and a LOAEL of 10 mg/kg/day. Additionally, the manufacturing process for 2,4,5-T contaminates this chemical with trace amounts of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD). TCDD is a carcinogenic persistent organic pollutant with long-term effects on the environment. With proper temperature control during production of 2,4,5-T, TCDD levels can be held to about .005 ppm. Before the TCDD risk was well understood, early production facilities lacked proper temperature controls and individual batches tested later were found to have as much as 60 ppm of TCDD.

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Dichlorvos

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Bromacil Chemical compound

Bromacil is an organic compound with the chemical formula C9H13BrN2O2, commercially available as a herbicide. Bromacil was first registered as a pesticide in the U.S. in 1961. It is used for brush control and non-cropland areas. It works by interfering with photosynthesis by entering the plant through the root zone and moving throughout the plant. Bromacil is one of a group of compounds called substituted uracils. These materials are broad spectrum herbicides used for nonselective weed and brush control on non-croplands, as well as for selective weed control on a limited number of crops, such as citrus fruit and pineapple. Bromacil is also found to be excellent at controlling perennial grasses.

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Bentazon Chemical compound

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References

  1. 1 2 3 4 5 6 7 NIOSH Pocket Guide to Chemical Hazards. "#0514". National Institute for Occupational Safety and Health (NIOSH).
  2. "Picloram".
  3. 1 2 Picloram Pesticide Information Profile, Pesticide Management Education Program, Cornell University.
  4. Stanley A. Greene (2005). Sittig's Handbook of Pesticides and Agricultural Chemicals. William Andrew. p. 717. ISBN   978-0-8155-1903-4.
  5. Committee to Review the Health Effects in Vietnam Veterans of Exposure to Herbicides; Institute of Medicine (1994). Veterans and Agent Orange: Health Effects of Herbicides Used in Vietnam. National Academies Press. pp. 89–90. ISBN   978-0-309-55619-4.
  6. Consumer Factsheet on: PICLORAM, U.S. Environmental Protection Agency
  7. Use Caution When Harvesting and Feeding Ditch Hay Archived 2010-06-14 at the Wayback Machine , U. Minnesota Extension
  8. NIOSH Pocket Guide to Chemical Hazards, Centers for Disease Control and Prevention