Mandipropamid

Chemical Properties

Dicynamid pure product is light yellow powder, melting point 96.4~97.3 ℃, vapor pressure <9.4×10-4mPa(25~50 ℃), distribution coefficient Kow lgP=3.2, Henry's coefficient <9.2×10-5 Pa-m3/mol(25 ℃, calculated value), density(22 ℃)1.24g/L. Solubility in water 4.2mg Solubility in water 4.2mg/L(25℃); Solubility in organic solvents (25℃, g/L): n-hexane 0.042, n-octanol 4.8, toluene 29, methanol 66, ethyl acetate 120, acetone 300, dichloromethane 400 Stable in pH=4~9.

Uses

Mandipropamid is a fungicide. It can be used on many fruit and vegetable crops, including potatoes, tomatoes, salad leaves and grapes. Manufactured by Syngenta.

Definition

ChEBI: 2-(4-chlorophenyl)-N-{2-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]ethyl}-2-(prop-2-yn-1-yloxy)acetamide is a monocarboxylic acid amide resulting from the condensation of the carboxy group of p-chloromandelic acid propargyl ether with the amino group of 2-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]ethylamine. It is a monocarboxylic acid amide, a terminal acetylenic compound, an aromatic ether and a member of monochlorobenzenes.

Production Methods

The industrial production of mandipropamid begins with the preparation of key intermediates such as 4-chloroacetophenone and vanillin, which undergo condensation and oxidation reactions to form a substituted aromatic ketone. This intermediate is then coupled with a cyclopropyl-containing oxazole derivative through a Friedel–Crafts acylation or similar electrophilic substitution, forming the central methanone bridge. The next step involves constructing the amide bond by reacting the ketone with an amine or ammonia derivative under mild conditions, yielding the final active compound: (RS)-2-(4-chlorophenyl)-N-(cyclopropylmethoxy)-N-(2-methoxyphenyl)acetamide. The synthesis is optimised to avoid protecting groups, simplifying purification and reducing waste.

Biological Activity

Mandipropamid (Mandi) is an agrochemical extensively used as fungicide. Mandipropamid specifically induces complex formation between a sixfold mutant of the plant hormone receptor pyrabactin resistance 1 (PYR1) and abscisic acid insensitive (ABI). Mandipropamid is a highly cell permeable, low toxic chemical inducers of proximity in vivo. It induces rapid colocalization of proteins contained fused receptor domain PYRMandi and receiver domain ABI.

Mechanism of action

Inhibits spore germination with preventative action. Cellulose synthesis inhibitor.

storage

Store at -20°C

Pesticide Type

Fungicide