110488-70-5 Usage
Description
Dimethomorph is a cinnamic acid derivative and a member of the morpholine chemical family, used as a systemic fungicide to protect against various fungal pathogens in vines and other crops. It is a mixture of Eand Z-isomers in the ratio of about 1:1, with only the Z-isomer possessing fungicidal activity. Its fungicidal activity works by inhibiting sterol (ergosterol) synthesis, which is essential for fungal cell wall formation.
Used in Agricultural Industry:
Dimethomorph is used as a fungicide for protecting crops from mold and fungal diseases. It exhibits protectant, curative, and antisporulant activities, making it effective against fungal diseases such as leaf blight, downy mildew, damping off, and foot-rot caused by Phytophthora spp. in grapes, potatoes, and tomatoes.
Dimethomorph is also used as a wood preservative to control downy mildew and is effective against downy mildews, late blights, anthracnose, septoria leaf spot, crown rot, and root rot for cucurbits, grapevines, head lettuce, onions, potatoes, tomatoes, and fruit including blackberries, raspberries, and strawberries.
In addition to its agricultural uses, Dimethomorph has shown inhibitory activity against androgen receptor (AR) in a reporter assay in MDA-kb2 human breast cancer cells, although it does not show activity in a yeast antiandrogen screen. It is not toxic to rats (LD50 = 3,900 mg/kg) or goldfish (C. auratus; LC50 = >32 μg/ml).
References
[1] http://www.fao.org
[2] http://pmep.cce.cornell.edu
[3] http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/245.htm
Trade name
ACROBAT? WP; FORUM DC?, [manco-
zeb + dimethomorph]; CME 151?; STATURE?
Metabolic pathway
Limited data are available in the open literature. Information presented in
this summary is abstracted from the data evaluation published by the
Pesticide Safety Directorate (PSD, 1994). Dimethomorph is a (1:l) mixture
of the E- and Z-isomers. The Z-isomer has been shown to have all the
intrinsic biological activities. The isomerisation of the E- and Z-isomers
was observed when resolved isomers were exposed to UV light. Dimethomorph
undergoes extensive degradation and metabolism in soil,
plants and animals. The major metabolic pathway is the O-demethylation
of one of the phenolic methoxy moieties to the corresponding phenols
and conjugates. Other metabolic reactions include the oxidation of one of
the CH2 moieties of the morpholine ring and the cleavage/opening of
the morpholine ring (Scheme 1).
Degradation
Dimethomorph (1) is hydrolytically stable with no observable degradation
in pH 4-9 buffered solutions at 70-90 °C for up to 10 weeks.
Degradation occurred when dimethomorph in pH 5 buffer solution was
irradiated under Hanau Suntest apparatus (<290 nm) at 25 °C. The calculated
aqueous photolytic degradation half-life (DT50) was ca. 25-28 days of
continuous irradiation, No sigruficant degradation product (>7% of the
applied radioactivity) was identified.
Check Digit Verification of cas no
The CAS Registry Mumber 110488-70-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,0,4,8 and 8 respectively; the second part has 2 digits, 7 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 110488-70:
(8*1)+(7*1)+(6*0)+(5*4)+(4*8)+(3*8)+(2*7)+(1*0)=105
105 % 10 = 5
So 110488-70-5 is a valid CAS Registry Number.
InChI:InChI=1/C21H22ClNO4/c1-25-19-8-5-16(13-20(19)26-2)18(15-3-6-17(22)7-4-15)14-21(24)23-9-11-27-12-10-23/h3-8,13-14H,9-12H2,1-2H3/b18-14+
110488-70-5Relevant articles and documents
Method for catalytically synthesizing dimethomorph by using Lewis base
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Paragraph 0016-0019, (2021/03/18)
The invention relates to the technical field of dimethomorph production, and particularly discloses a method for catalytically synthesizing dimethomorph by using a Lewis base. According to the method,benzophenone and acetylmorpholine are subjected to a low-temperature reaction, an intermediate-state product is prepared in the presence of a solvent and the Lewis base, and then an elimination reaction is carried out under the high-temperature condition to remove one molecule of water, so that the product is obtained. The method has the advantages of concise and reliable synthetic route, low consumption of the raw material acetylmorpholine, easy control of the reaction, low cost of the obtained product, less generation of three wastes, and high economic and environmental protection values.
Dimethomorph production method
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Paragraph 0011; 0012; 0013, (2018/06/15)
The invention discloses a dimethomorph production method in the technical field of pesticide production. The production method comprises: 1) synthesizing veratrole; 2) synthesizing 3,4-dimethoxy-4-chloro-benzophenone; 3) synthesizing acetylmorpholine; and 4) synthesizing dimethomorph. Sodium tert-butoxide is taken as a basic catalyst for synthesizing dimethomorph from 3,4-dimethoxy-4-chloro-benzophenone and acetylmorpholine, and a sodium hydroxide solution is used to perform alkali washing on a reactant in a reaction vessel. Sodium hydroxide has a catalytic effect on synthesis of dimethomorphfrom 3,4-dimethoxy-4-chloro-benzophenone and acetylmorpholine. The defect that the catalytic effect of sodium tert-butoxide is gradually reduced due to unstable chemical property of sodium tert-butoxide and degradation of sodium tert-butoxide when sodium tert-butoxide comes into water is overcome. The dimethomorph product is improved in conversion rate and purity.
FUNGICIDAL MIXTURES
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, (2012/04/18)
The present invention relates to fungicidal mixtures comprising, as active components, 1) azolylmethyloxiranes of the general formula I in which the variables have the meanings described in the application, and 2) a fungicidal compound II, where the compounds II of component 2 are selected from among the compounds described in the application, and to the use of the fungicidal mixtures for controlling phytopathogenic fungi and to the compositions comprising them.