General Description
White crystalline solid. Used as a fungicide.
Reactivity Profile
Acidic organic/inorganic salts, such as DODINE(2439-10-3), are generally soluble in water. The resulting solutions contain moderate to high concentrations of hydrogen ions and have pH's of less than 7.0. They react as acids to neutralize bases. These neutralizations generate heat, but less or far less than is generated by neutralization of inorganic acids, inorganic oxoacids, and carboxylic acid. They usually do not react as either oxidizing agents or reducing agents but such behavior is not impossible. Many of these compounds catalyze organic reactions.
Air & Water Reactions
Soluble in hot water.
Description
Dodine is a guanidine fungicide which is currently approved for use in both the UK and the EU. It is moderately soluble in water but not most organic solvents. It tends not to be persistent in soil and is non-mobile. Based on its physico-chemical parameters, dodine is not expected to leach to groundwater. It demonstrates a moderate toxicity to mammals, birds and fish but is highly toxic to aquatic invertebrates and algae. It is less toxic to bees. Limited data is available on its toxicity to humans it is considered moderately toxic via the oral route.
Chemical Properties
White Solid
Uses
Agricultural fungicide.
Uses
Dodine is used to control scab on apples, pears and pecans, leaf
spot diseases of cherries, olives, blackcurrants, celery and other crops, and
foliar diseases of strawberries. It is also used on other fruit, vegetable, nut
and ornamental crops and shade trees.
Uses
Used as agricultural fungicide.
Definition
ChEBI: An acetate salt resulting from the reaction of equimolar amounts of 1-dodecylguanidine and acetic acid. It is used as a fungicide to control black spot and foliar diseases on apples, pears, peaches, nectarines and strawberries.
Production Methods
The commercial production of dodine involves the reaction of dodecylamine (a long-chain aliphatic amine) with cyanamide to form dodecylguanidine as the primary intermediate. This guanidine derivative is then neutralised with acetic acid to yield the acetate salt, forming dodine. The process requires careful control of reaction conditions, particularly temperature and pH, to ensure complete conversion and minimize byproducts. After synthesis, the product is typically purified, dried, and formulated
Agricultural Uses
Fungicide, Microbiocide: Used to control black spot on apples, pears and pecans;
brown rot and foliar diseases on peaches and nectarines,
cherries, strawberries, black walnuts and sycamore
trees. In industry, used as a biocide and preservative. May
also be used to catalyze organic reactions.
Trade name
AC 5223®; AMERICAN CYANAMID®
5223; APADODINE®; CARPENE®; CURITAN®;
CYPREX®; CYPREX® 65W; CYTOX® 2160;
DOQUADINE®; EFUZIN®; KARPEN®; MELPREX®;
MELPREX® 65; MILPREX®; QUESTURAN®; Radspor
L; SULGEN®; SYLLIT®; SYLLIT® 65; SYLLIT®
400SC, TEBULAN®; TSITREX®; VANDODINE®;
VENTUROL®; VONDODINE®
Mechanism of action
Systemic with protectant and eradicant action. Cell membrane disruption.
Metabolic pathway
No information is available on the fate of dodine in soils but in plants it is
converted into creatine by the action of a methyltransferase, and simultaneously
the dodecyl moiety is oxidatively cleaved (PM).
Degradation
Dodine is stable in neutral and moderately alkaline or acidic media but
the free base is liberated by concentrated alkali (PM).
