2,4-Dichlorophenoxyacetic acid

2,4-Dichlorophenoxyacetic acid (usually referred to by its

abbreviation, 2,4-D) is a common systemic herbicide used
in the control of broadleaf weeds. It is one of the most
widely used herbicides in the world. 2,4-D is a synthetic
auxin (plant hormone), and as such it is often used in
laboratories for plant research and as a supplement in plant
cell culture media such as MS medium.
2,4-D was one of the ingredients in Agent Orange, the
herbicide widely used during the Vietnam war. According to the US National Pesticide Information
Center, "the controversy regarding health effects centered around the 2,4,5-T component of the
herbicide and its contaminant, dioxin
Production
2,4-D is manufactured from 2,4-dichlorophenol in a four
step process:
Step 1 - Phenol neutralisation
The (acidic) phenol is neurtralised with caustic soda.
2,4-dicholorophenol + NaOH sodium dichlorophenate
(NaDCP) + H2O + heat
Step 2 - NaMCA production
Sodium monochloroacetate is produced in another
exothermic reaction.
monochloroacetic acid (MCAA) + NaOH sodium
monochloroacetate (NaMCA) + H2O
Step 3 - Condensation
The NaDCP is condensed with NaMCA to produce Na 2,4-D
- the sodium salt of 2,4-D. NaDCP + NaMCA sodium
2,4dichlorophenoxyacetate + NaCl
Step 4 - Final ageing
The Na 2,4-D is aged by the slow addition of NaOH to
ensure that the phenol content is less than 0.5 w/w%. This
Na 2,4-D is then converted to its ethyl hexylester,
emulsified and sold as a herbicide.

Uses
Primarily used as a synthetic auxin
analog, as an herbicide. It is sold in
various formulations under a wide
variety of brand names, most
commonly used for weed control in
lawns and other turf and control of
weeds and brush along fences and
highway and railroad rights of way.
Toxicity
According to the US Environmental
Protection Agency (EPA), exposure
to 2,4-D has reported to result in:
Blood, liver, and kidney toxicity.
Chronic oral exposure resulted in
eye, thyroid, kidney, adrenals and
ovaries/testes.
Delayed
neurobehavioral
development
Reduction in hemoglobin and RBC
numbers. Decreased liver enzyme
activity. Burning sensations in lungs
Loss of muscular coordination, and
coma

2,4,5-Trichlorophenoxyacetic acid
2,4,5-Trichlorophenoxyacetic acid (also known as 2,4,5-T),
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 (2,4dichlorophenoxyacetic acid).

Production

The synthesis of 2,4,5-T is similarto that for 2,4-D

Uses
2,4,5-T was used mainly for control
of perennial broad-leaved weed
species and deciduous brush
species in non-crop areas,
including rough grass pastures,
farmyards, ditchbanks, industrial
sites, and rights of way, such as
under
hydro
and
telecommunications lines, along
roadsides, highways, fencerows,
and along railway tracks. It was
also used for conifer releaseand in
site preparation for planting of
coniferous
tree
species.
Authorities of parks, golf courses,
and other recreational areas were
permitted
to
apply
some
formulations of 2,4,5-T for control
of poison ivy.

Toxicity
2,4,5-T itself is toxic with a NOAEL
of 3 mg/kg/day and a LOAEL of 10
mg/kg/day. It is also the root cause
of lethality in Agent Orange.

Hexanoic acid (C6H12O2)

Hexanoic acid (caproic acid), is the carboxylic acid derived
from hexane with the general formula C5H11COOH. It is a
colorless oily liquid with an odor that is fatty, cheesy, waxy,
and like that of goats, or other barnyard animals. It is a fatty
acid found naturally in various animal fats and oils, and is
one of the chemicals that give the decomposing fleshy seed
coat of the ginkgo its characteristic unpleasant odor. It is
also one of the components of vanilla. Other names include
caproic acid, caprylic acid and capronic acid.

Production

From crude fermentation of butyric

acid, fractional distillation of natural
fatty acids.

Uses
The primary use of hexanoic acid is in the
manufacture of its esters for artificial flavors, and in
the manufacture of hexyl derivatives, such as
hexylphenols. In addition, it is also commonly used
in butter, milk, cream, strawberry, bread, beer, but
and other flavors.

Toxicity
Acute Exposure/ Caproic acid is a mild skin irritant
and severe eye irritant in rabbits. A mild response
occurred in rabbits when 10 mg of the compound or 465 mg was applied to open skin patches for 24
hr; a 15% solution of caproic acid produced severe burns of the rabbit cornea.
References

Tschirley FH. Defoliation in Vietnam. Science. 1969;163:779-786.

Orians GH, Pfeiffer EW. Ecological effects of the war in Vietnam. Science. 1970;168:544554.
Neilands JB, Orians GH, Pfeiffer EW, Vennema A, Westing AH. Harvest of Death: Chemical
Warfare in Vietnam and Cambodia. New York: Free Press; 1972.
<http://pubchem.ncbi.nlm.nih.gov/compound/hexanoic_acid>
<http://www.pesticideinfo.org/Detail_Chemical.jsp?Rec_Id=PC33719>