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Dimethomorph

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Dimethomorph Basic information
Description References
Product Name:Dimethomorph
Synonyms:4-(3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl)-morpholin (e,z)-4-[3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]morpholine (e,z)-4-[3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)acryloyl]morpholine 4-(3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl)morpholine;Dimethomorph W.P.(50%);Festival C;Dimethomorph 100mg [110488-70-5];3-(4-Chlorophenyl)-3-(3,4-diMethoxyphenyl)-1-(4-Morpholinyl)-2-propen-1-one;3-(4-Chlorophenyl)-3-(3,4-diMethoxyphenyl)-1-Morpholinoprop-2-en-1-one;Dimethomorph 0;Factory hot sell Dimethomorph CAS:110488-70-5 with best price
CAS:110488-70-5
MF:C21H22ClNO4
MW:387.86
EINECS:404-200-2
Product Categories:Agro-Products;Aromatics;Heterocycles;INSECTICIDE;Pesticides&Metabolites;Morpholines;Fungicides;DID - DINPesticides;DAlphabetic;D;Alpha sort
Mol File:110488-70-5.mol
Dimethomorph Structure
Dimethomorph Chemical Properties
Melting point 125-149°C
Boiling point 584.9±50.0 °C(Predicted)
density 1.231±0.06 g/cm3(Predicted)
vapor pressure 1 x 10-6 Pa (25 °C)
storage temp. Sealed in dry,Room Temperature
solubility Chloroform: Soluble,Methanol: Soluble
pka-1.19±0.20(Predicted)
form Solid
Water Solubility 50 mg l-1 (20-23 °C)
color White to off-white
Merck 13,3248
BRN 8794474
Major Applicationagriculture
environmental
InChI1S/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+
InChIKeyQNBTYORWCCMPQP-NBVRZTHBSA-N
SMILESCOc1ccc(cc1OC)\C(=C\C(=O)N2CCOCC2)c3ccc(Cl)cc3
LogP2.680
EPA Substance Registry SystemDimethomorph (110488-70-5)
Safety Information
Hazard Codes N
Risk Statements 51/53
Safety Statements 61
RIDADR UN3077 9/PG 3
WGK Germany 2
RTECS QE0478300
Storage Class6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects
Hazard ClassificationsAquatic Chronic 2
Repr. 1B
Hazardous Substances Data110488-70-5(Hazardous Substances Data)
ToxicityLD50 in rats (mg/kg): 321 i.p.; 3900 orally; >5000 dermally; LC50 (4-hr inhalation): >4.2 mg/ml (Veenstra, Owen)
MSDS Information
ProviderLanguage
Dimethomorph English
Dimethomorph Usage And Synthesis
DescriptionDimethomorph is a cinnamic acid derivative and a member of the morpholine chemical family. Dimethomorph is a mixture of E- and Z-isomers in the ratio of about 1:1 and only the Z-isomer has the fungicidal activity. It fungicidal activity works by the inhibition of sterol (ergosterol) synthesis.
Dimethomorph is a systemic fungicide to protect against various fungal pathogens in vines and other crops. Dimethomorph is used to against downy mildews, late blights, anthracnose, septoria leaf spot, crown rot, and root rot for curbubits, grapevines, head lettuce, onions, potatoes, tomatoes, and fruit including blackberries, raspberries, strawberries.
References[1] http://www.fao.org
[2] http://pmep.cce.cornell.edu
[3] http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/245.htm
DescriptionDimethomorph is a morpholine fungicide that inhibits fungal cell wall formation. It inhibits mycelial growth of the oomycete fungi P. citrophthora, P. parasitica, P. capsici, and P. infestans (EC50s = 0.14, 0.38, <0.1, and 0.16-0.3 μg/ml, respectively) but is less active against the green algae species C. vulgaris or S. obliquus in vitro (EC50s = 47.46 and 44.87 μg/ml, respectively). It inhibits androgen receptor (AR) activity in a reporter assay in MDA-kb2 human breast cancer cells but not in a yeast antiandrogen screen (IC20s = 0.263 and 38.5 μM, respectively). It is not toxic to rats (LD50 = 3,900 mg/kg) or goldfish (C. auratus; LC50 = >32 μg/ml).
Chemical PropertiesOff-White Solid
UsesDimethomorph is a systemic fungicide which exhibits protectant, curative and antisporulant activities. It is active against fungal diseases such as leaf blight, downy mildew, damping off and foot-rot caused by Phytophthora spp. in/on grapes, potatoes and tomatoes.
UsesAgricultural fungicide.
DefinitionChEBI: A mixture of (E)- and (Z)-dimethomorph in an unspecified ratio. It is used as a systemic fungicide used on vines, potatoes, and greenhouse crops; only the Z isomer has fungicidal activity.
Agricultural UsesFungicide: A systemic fungicide that protects crops from mold. It also kills mold and prevents their spread; controls late blight on tomatoes; and is used as a wood preservative to control downey mildew.
Trade nameACROBAT® WP; FORUM DC®, [manco- zeb + dimethomorph]; CME 151®; STATURE®
SynthesisThe first step: xylene and acetic anhydride at room temperature stirring drop of morpholine, drop the end of the slow increase in temperature to 110 ??, reflux insulation 5h, after the end of the over into the distillation kettle desolvation and by-products of acetic acid, the kettle residual part for the intermediate acetyl morpholine The residual part in the kettle is the intermediate acetylmorpholine, the content is more than or equal to 99%, the yield is more than or equal to 90.2%.
The second step: in the reaction kettle into xylene, E-phenyl ketone and amino sodium, stirring temperature to 100 ?? when adding acetomorpholine drops, droplet finished temperature to 110 ?? reflux insulation 2h, insulation end of the temperature to 80 ?? over the wash kettle divided into Out of the waste lye, after washing to neutral water into the distillation kettle recovery of xylene, centrifugal drying enoymorpholine, content greater than or equal to 95%, yield greater than or equal to 76.6%.
In this method, sodium amide is used to replace sodium tert-butoxide in traditional technology, which greatly improves the reaction speed, shortens the reaction time from 10h to 2h, and greatly improves the production efficiency.
Metabolic pathwayLimited 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).
DegradationDimethomorph (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.
References[1] (EFSA) E F S A. Conclusion regarding the peer review of the pesticide risk assessment of the active substance dimethoate[C]//4 7. 2006. DOI: 10.2903/j.efsa.2006.84r
[2] M E MATHERON  M P. Impact of Azoxystrobin, Dimethomorph, Fluazinam, Fosetyl-Al, and Metalaxyl on Growth, Sporulation, and Zoospore Cyst Germination of Three Phytophthora spp.[J]. Plant disease, 2000, 84 4: 454-458. DOI: 10.1094/pdis.2000.84.4.454
[3] XIAO-BO YU. Aquatic environmental safety assessment and inhibition mechanism of chemicals for targeting Microcystis aeruginosa.[J]. Ecotoxicology, 2014, 23 9: 1638-1647. DOI: 10.1007/s10646-014-1303-x
Dimethomorph Preparation Products And Raw materials
Preparation ProductsMancozeb+Dimethomorph,W.P.
Tag:Dimethomorph(110488-70-5) Related Product Information
Diphenyldimethoxysilane 1-Phenyl-2-nitropropene 4-Methylmorpholine 4-Acryloylmorpholine Morpholine 1,1-Dimethoxyethane DIPHENYLCYCLOPROPENONE 4-Methoxyphenylacetone Moroxydine 4-Formylmorpholine Dimethyldimethoxysilane morpholine 4-Cyclododecyl-2,6-dimethylmorpholine acetate 1-(1-(4-CHLOROPHENYL)VINYL)BENZENE Dimethomorph Dimethomorph,water-dispersion granule Z-DIMETHOMORPH SOLUTION 100UG/ML IN METHANOL 1ML 4-(3,3-Diphenylallyl)morpholine hydrochloride

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