75-99-0 Usage
Description
2,2-Dichloropropionic acid, also known as dalapon, is a commonly used herbicide for the control of annual and perennial grasses in croplands. It is a Class II toxic agent (moderately toxic) and can be caustic to human skin, damaging to the conjunctiva of the human eye, and irritating/damaging to the upper respiratory system of humans. Dalapon is translocated to the roots where it acts as a growth regulator. It is highly soluble and can readily move through the environment, but it is relatively safe and instances of dalapon intoxication are rare.
Uses
Used in Agriculture:
2,2-Dichloropropionic acid is used as a herbicide for the selective control of annual and perennial grass weeds in cropland and noncropland. It is also used as a selective aquatic herbicide.
Used in Various Crops:
2,2-Dichloropropionic acid is used to control grasses in a wide variety of crops, such as corn, potatoes, legume crops, citrus, fruit, and nut trees. It is also used on sugarcane, sugar beets, carrots, asparagus, alfalfa, and flax.
Used in Non-crop Applications:
2,2-Dichloropropionic acid is used in forestry, home gardening, and to control reed and sedge growth in aquatic environments. It is also used in noncrop applications, such as along drainage ditches, railroads, and in industrial areas.
Used as a Sodium or Magnesium Salt:
2,2-Dichloropropionic acid is marketed as the sodium salt or a mixture of the sodium and magnesium salts for its herbicidal properties.
Air & Water Reactions
Soluble in water. Reacts slowly in water to form hydrochloric and pyruvic acids.
Fire Hazard
Combustible. Irritating fumes of hydrochloric acid may form in fire. Volatilizes with steam.
Safety Profile
A corrosive with low
toxicity by skin contact. A skin irritant.
Mutation data reported. When heated to
decomposition it emits toxic fumes of Cl-
Environmental Fate
The mechanism of action of dalapon is the same as for most
acids. The acid denatures tissue proteins upon contact. At lower
concentrations, the dalapon causes nonlethal yellowing of
sensitive plants, which clearly distinguished them from resistant
plants. The mode of action of chlorinated aliphatic acids is
not known but they probably affect many enzyme pathways.
Dalapon is readily absorbed into roots and leaves of plants and
then translocated. Lower concentrations will inhibit plant
growth and cause leaf chlorosis, followed by necrosis and
death. Higher concentrations of dalapon will result in significant
necrosis of areas of the plant in contact with dalapon.
Although the direct mechanism of these effects has remained
elusive, it is thought that dalapon may affect lipid, carbohydrate,
and nitrogen metabolism as secondary effects. One
prevailing hypothesis for the primary dalapon affect is that
dalapon exerts direct effects on plant structural proteins leading
to these secondary metabolic outcomes.
Toxicity evaluation
Dalapon is somewhat persistent in soil but does not readily
adsorb to soil particles. It can remain active in soil for several
months when applied at high rates. In general, dalapon is
considered to have low to moderate persistence with detection
in soil for 2–8 weeks. Due to its inability to bind to soil
particles, dalapon has a relatively high mobility in soil, with
leaching possible. Microorganisms in the soil are very efficient
at degrading dalapon. The herbicide is usually not found below
the first 6 inches of soil layer. Breakdown is relatively rapid and
complete, leading to the production of compounds that are not
naturally occurring. Soil microorganisms are efficient at
degrading dalapon, however, such that dalapon is not typically
found in groundwater. High temperatures and increased
moisture accelerate dalapon degradation in soil. Dalapon can
also be degraded by ultraviolet light. In aquatic environments,
dalapon is degraded by microorganisms (most important),
hydrolysis, and photolysis. In the absence of microbial degradation,
the half-life of dalapon is several months or longer if
the water temperature is below 25°C, with the primary
hydrolysis product being pyruvate. Dalapon is absorbed by
both plant roots and leaves followed by translocation. With
high applications, dalapon precipitates and leads to local
corrosive effects on plants. Due to the ability of dalapon to be
rapidly metabolized and degraded by microorganisms,
hydrolyzed to pyruvate, rapidly translocated to plants, and
quickly moved through the environment, it is not expected that
dalapon will constitute any bioaccumulation hazard.
Check Digit Verification of cas no
The CAS Registry Mumber 75-99-0 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 5 respectively; the second part has 2 digits, 9 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 75-99:
(4*7)+(3*5)+(2*9)+(1*9)=70
70 % 10 = 0
So 75-99-0 is a valid CAS Registry Number.
InChI:InChI=1/C3H4Cl2O2/c1-3(4,5)2(6)7/h1H3,(H,6,7)/p-1
75-99-0Relevant articles and documents
New acyloxy nitroso compounds with improved water solubility and nitroxyl (HNO) release kinetics and inhibitors of platelet aggregation
Mohamed, Heba A.H.,Abdel-Aziz, Mohamed,Abuo-Rahma, Gamal El-Din A.A.,King, S. Bruce
, p. 6069 - 6077 (2015/11/10)
New acyloxy nitroso compounds, 4-nitrosotetrahydro-2H-pyran-4-yl 2,2,2-trichloroacetate and 4-nitrosotetrahydro-2H-pyran-4-yl 2,2-dichloropropanoate were prepared. These compounds release HNO under neutral conditions with half-lives between 50 and 120 min, identifying these HNO donors as kinetically intermediate to the much slower acetate derivative and the faster trifluoroacetic acid derivative. These compounds or HNO-derived from these compounds react with thiols, including glutathione, thiol-containing enzymes and heme-containing proteins in a similar fashion to other acyloxy nitroso compounds. HNO released from these acyloxy nitroso compounds inhibits activated platelet aggregation. These acyloxy nitroso compounds augment the range of release for this group of HNO donors and should be valuable tools in the further study of HNO biology.
Oxidation of aliphatic 2,2-dichloroalkanals by HNO3 in CH 2Cl2: An easy and eco-friendly route to the corresponding 2,2-dichloroalkanoic acids
Bellesia, Franco,De Buyck, Laurent,Ghelfi, Franco,Pagnoni, Ugo M.,Strazzolini, Paolo
, p. 1473 - 1481 (2007/10/03)
A simple, economically convenient, and eco-compatible procedure for the oxidation of 2,2-dichloroalkanals to the corresponding alkanoic acids has been set up, employing HNO3 in CH2O2, in the presence of NaNO2 as catalyst.
2,2-dichloroaldehydes and 2,2-dichlorocarboxylic acids from 2- picoline·HCl catalyzed chlorination of aldehydes
Bellesia, Franco,De Buyck, Laurent,Ghelfi, Franco
, p. 146 - 148 (2007/10/03)
An efficient preparation of 2,2-dichloroaldehydes and 2,2- dichlorocarboxylic acids has been achieved by chlorination of aldehydes using 2-picoline hydrochloride as recoverable catalyst.