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fenpropimorph
cis-4-[3-[4-(1,1-dimethylethyl)phenyl]-2-methylpropyl]-2,6-dimethylmorpholine (9CI)

Supplier Sponsors

CAS Number: 67564-91-4Picture of molecule3D/inchi
Other(deleted CASRN):67306-03-0
ECHA EINECS - REACH Pre-Reg:266-719-9
FDA UNII: 4548UM725F
Nikkaji Web:J310.265C
Beilstein Number:884767
MDL:MFCD00144306
XlogP3-AA:5.20 (est)
Molecular Weight:303.48921000
Formula:C20 H33 N O
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:herbicides / pesticides
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 392.70 °C. @ 760.00 mm Hg (est)
Flash Point: 240.00 °F. TCC ( 115.60 °C. ) (est)
logP (o/w): 4.930
Soluble in:
 water, 7.354 mg/L @ 25 °C (est)
 water, 4.3 mg/L @ 20 °C (exp)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Carbosynth
For experimental / research use only.
Fenpropimorph
Glentham Life Sciences
Fenpropimorph
Santa Cruz Biotechnology
For experimental / research use only.
Fenpropimorph
Sigma-Aldrich: Sigma
For experimental / research use only.
Fenpropimorph PESTANAL®, analytical standard
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-mouse LD50 5980 mg/kg
Pesticide Manual. Vol. 9, Pg. 379, 1991.

oral-rat LD50 3000 mg/kg
Pesticide Manual. Vol. 9, Pg. 379, 1991.

Dermal Toxicity:
skin-rat LD50 4200 mg/kg
Pesticide Manual. Vol. 9, Pg. 379, 1991.

Inhalation Toxicity:
inhalation-rat LC50 2900 mg/m3/4H
Pesticide Manual. Vol. 9, Pg. 379, 1991.
 
Safety in Use Information:
Category:
herbicides / pesticides
Recommendation for fenpropimorph usage levels up to:
 not for fragrance use.
 
Recommendation for fenpropimorph flavor usage levels up to:
 not for flavor use.
 
Safety References:
European Food Safety Authority (EFSA) reference(s):

Reasoned opinion on the modification of the existing MRLs for fenpropimorph in cereals and commodities of animal origin
View page or View pdf

Reasoned opinion on the review of the existing maximum residue levels (MRLs) for fenpropimorph according to Article 12 of Regulation (EC) No 396/2005
View page or View pdf

Retrospective analysis of the immunotoxic effects of plant protection products as reported in the Draft Assessment Reports for their peer review at EU level
View page or View pdf

EPI System: View
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :93365
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(2R,6S)-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine
Chemidplus:0067564914
RTECS:QE1940000 for cas# 67564-91-4
 
References:
 (2R,6S)-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):93365
Pubchem (sid):135048275
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEMBL:View
KEGG (GenomeNet):C18787
HMDB (The Human Metabolome Database):HMDB37270
FooDB:FDB016288
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 not found in nature
 
Synonyms:
cis-4-(3-(para-tert-butyl phenyl)-2-methyl propyl)-2,6-dimethyl morpholine
cis-4-(3-(p-tert-butylphenyl)-2-methylpropyl)-2,6-dimethylmorpholine
(2R,6S)-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine
(2R,6S)-4-[3-(p-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine
cis-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine
cis-4-[3-(p-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine
cis-2,6-dimethyl-4-(3-(4-(1,1-dimethylethyl)phenyl)-2-methylpropyl)morpholine
(2R,6S)-2,6-dimethyl-4-{2-methyl-3-[4-(2-methyl-2-propanyl)phenyl]propyl}morpholine
cis-4-(3-(4-(1,1-dimethylethyl)phenyl)-2-methylpropyl)-2,6-dimethylmorpholine
cis-4-[3-[4-(1,1-dimethylethyl)phenyl]-2-methylpropyl]-2,6-dimethylmorpholine (9CI)
 fenpropimorphe
 funbas
 mildofix
 mistral T
 morpholine, 2,6-dimethyl-4-[3-[4-(1,1-dimethylethyl)phenyl]-2- methylpropyl]-, cis-
 morpholine, 4-(3-(4-(1,1-dimethylethyl)phenyl)-2-methylpropyl)-2,6-dimethyl-, (2R,6S)-rel-
 morpholine, 4-[3-[4-(1,1-dimethylethyl)phenyl]-2-methylpropyl]-2,6-dimethyl-, (2R,6S)-
 morpholine, 4-[3-[4-(1,1-dimethylethyl)phenyl]-2-methylpropyl]-2,6-dimethyl-, cis-
 

Articles:

PubMed:Untargeted profiling of pesticide metabolites by LC-HRMS: an exposomics tool for human exposure evaluation.
PubMed:Identification and functional analysis of the primary pantothenate transporter, PfPAT, of the human malaria parasite Plasmodium falciparum.
PubMed:Sterols are required for cell-fate commitment and maintenance of the stomatal lineage in Arabidopsis.
PubMed:Highly concentrated emulsified microemulsions as solvent-free plant protection formulations.
PubMed:Effect of fenpropimorph, prochloraz and tebuconazole on growth and production of T-2 and HT-2 toxins by Fusarium langsethiae in oat-based medium.
PubMed:Sorption of biocides, triazine and phenylurea herbicides, and UV-filters onto secondary sludge.
PubMed:Fenpropimorph and fenhexamid impact phosphorus translocation by arbuscular mycorrhizal fungi.
PubMed:Synergism between demethylation inhibitor fungicides or gibberellin inhibitor plant growth regulators and bifenthrin in a pyrethroid-resistant population of Listronotus maculicollis (Coleoptera: Curculionidae).
PubMed:Synthesis and characterization of N,N-dialkyl and N-alkyl-N-aralkyl fenpropimorph-derived compounds as high affinity ligands for sigma receptors.
PubMed:Characterization of a CuZn superoxide dismutase gene in the arbuscular mycorrhizal fungus Glomus intraradices.
PubMed:Pesticide cocktails can interact synergistically on aquatic crustaceans.
PubMed:Toxicity of fungicides to natural bacterial communities in wetland water and sediment measured using leucine incorporation and potential denitrification.
PubMed:Arbuscular mycorrhiza partially protect chicory roots against oxidative stress induced by two fungicides, fenpropimorph and fenhexamid.
PubMed:Baseline sensitivity to proquinazid in Blumeria graminis f. sp. tritici and Erysiphe necator and cross-resistance with other fungicides.
PubMed:Fenpropimorph slows down the sterol pathway and the development of the arbuscular mycorrhizal fungus Glomus intraradices.
PubMed:Functional characterization of a C-4 sterol methyl oxidase from the endomycorrhizal fungus Glomus intraradices.
PubMed:Differential effects of fenpropimorph and fenhexamid, two sterol biosynthesis inhibitor fungicides, on arbuscular mycorrhizal development and sterol metabolism in carrot roots.
PubMed:Novel chamber to measure equilibrium soil-air partitioning coefficients of low-volatility organic chemicals under conditions of varying temperature and soil moisture.
PubMed:Probing the steroid binding domain-like I (SBDLI) of the sigma-1 receptor binding site using N-substituted photoaffinity labels.
PubMed:Effects of two sterol biosynthesis inhibitor fungicides (fenpropimorph and fenhexamid) on the development of an arbuscular mycorrhizal fungus.
PubMed:Survival in the presence of antifungals: genome-wide expression profiling of Aspergillus niger in response to sublethal concentrations of caspofungin and fenpropimorph.
PubMed:Identification of regions of the sigma-1 receptor ligand binding site using a novel photoprobe.
PubMed:Factors influencing degradation of pesticides in soil.
PubMed:Lipids: architects and regulators of membrane dynamics and trafficking.
PubMed:Sterol demethylation inhibitor fungicides as disruptors of insect development and inducers of glutathione S-transferase activities in Mamestra brassicae.
PubMed:Prediction of the adsorption of ionizable pesticides in soils.
PubMed:Comparison of wind tunnel and field experiments to measure potential deposition of fenpropimorph following volatilisation from treated crops.
PubMed:Insights into the role of specific lipids in the formation and delivery of lipid microdomains to the plasma membrane of plant cells.
PubMed:Volatilization of the pesticides chlorpyrifos and fenpropimorph from a potato crop.
PubMed:Common pesticide increases costs of antipredator defenses in Rana temporaria tadpoles.
PubMed:Specific patterns of changes in wheat gene expression after treatment with three antifungal compounds.
PubMed:A latent variable model for chemogenomic profiling.
PubMed:Pesticide retention in the watershed and in a small constructed wetland treating diffuse pollution.
PubMed:Cold-climate vegetative buffer zones as pesticide-filters for surface runoff.
PubMed:Measured and computed volatilisation of the fungicide fenpropimorph from a sugar beet crop.
PubMed:Pesticide volatilization from plants: improvement of the PEC model PELMO based on a boundary-layer concept.
PubMed:A link between sterol biosynthesis, the cell wall, and cellulose in Arabidopsis.
PubMed:Subsurface tile drainage loss of modern pesticides: field experiment results.
PubMed:The Candida albicans lanosterol 14-alpha-demethylase (ERG11) gene promoter is maximally induced after prolonged growth with antifungal drugs.
PubMed:Screening the retention of thirteen pesticides in a small constructed wetland.
PubMed:Cyclic AMP signaling pathway modulates susceptibility of candida species and Saccharomyces cerevisiae to antifungal azoles and other sterol biosynthesis inhibitors.
PubMed:Pesticide volatilization from soil: lysimeter measurements versus predictions of European registration models.
PubMed:Impact of strobilurins on physiology and yield formation of wheat.
PubMed:Sterols regulate development and gene expression in Arabidopsis.
PubMed:Ergosterol biosynthesis inhibitors become fungicidal when combined with calcineurin inhibitors against Candida albicans, Candida glabrata, and Candida krusei.
PubMed:Effects of three fungicides alone and in combination on glutathione S-transferase activity (GST) and cytochrome P-450 (CYP 1A1) in the liver and gill of brown trout (Salmo trutta).
PubMed:Histone deacetylase inhibitors enhance Candida albicans sensitivity to azoles and related antifungals: correlation with reduction in CDR and ERG upregulation.
PubMed:Inhibition of the sterol pathway in leek seedlings impairs phosphatidylserine and glucosylceramide synthesis but triggers an accumulation of triacylglycerols.
PubMed:Semi-volatile organic compounds at the leaf/atmosphere interface: numerical simulation of dispersal and foliar uptake.
PubMed:Measurement of xylem translocation of weak electrolytes with the pressure chamber technique.
PubMed:The influence of newly synthesised fenporpimorph derivatives on some pathogen yeasts.
PubMed:Aberrant pathways in the late stages of cholesterol biosynthesis in the rat. Origin and metabolic fate of unsaturated sterols relevant to the Smith-Lemli-Opitz syndrome.
PubMed:Upregulation of ERG genes in Candida species by azoles and other sterol biosynthesis inhibitors.
PubMed:Use of supercritical fluid extraction in the analysis of pesticides in soil.
PubMed:The distribution of micro-organic contaminants in river bed-sediment cores.
PubMed:Sterol metabolism and ERG2 gene regulation in the yeast Saccharomyces cerevisiae.
PubMed:The fenpropimorph resistance gene FEN2 from Saccharomyces cerevisiae encodes a plasma membrane H+-pantothenate symporter.
PubMed:A calcium-dependent ergosterol mutant of Saccharomyces cerevisiae.
PubMed:Human lamin B receptor exhibits sterol C14-reductase activity in Saccharomyces cerevisiae.
PubMed:Both the immunosuppressant SR31747 and the antiestrogen tamoxifen bind to an emopamil-insensitive site of mammalian Delta8-Delta7 sterol isomerase.
PubMed:Influence of new fenpropimorph fungicides on the growth and sterol composition in Saccharomyces cerevisiae: relationship between structure and activity.
PubMed:Genetic analysis of resistance to fenpropimorph in Aspergillus niger.
PubMed:High affinity of sigma 1-binding sites for sterol isomerization inhibitors: evidence for a pharmacological relationship with the yeast sterol C8-C7 isomerase.
PubMed:Yeast sterol C8-C7 isomerase: identification and characterization of a high-affinity binding site for enzyme inhibitors.
PubMed:Transcriptional regulation by ergosterol in the yeast Saccharomyces cerevisiae.
PubMed:Emopamil-binding protein, a mammalian protein that binds a series of structurally diverse neuroprotective agents, exhibits delta8-delta7 sterol isomerase activity in yeast.
PubMed:Characterization of the Saccharomyces cerevisiae FMS1 gene related to Candida albicans corticosteroid-binding protein 1.
PubMed:FEN2: a gene implicated in the catabolite repression-mediated regulation of ergosterol biosynthesis in yeast.
PubMed:Isolation and characterization of the Saccharomyces cerevisiae SUT1 gene involved in sterol uptake.
PubMed:Neuroprotective sigma ligands interfere with the glutamate-activated NOS pathway in hippocampal cell culture.
PubMed:Effects of sterol biosynthesis inhibitors on phosphatidylcholine biosynthesis in Apium graveolens.
PubMed:Investigation of the role of sterol delta 8-->7-isomerase in the sensitivity of Saccharomyces cerevisiae to fenpropimorph.
PubMed:Fenpropimorph affects uptake of uracil and cytosine in Saccharomyces cerevisiae.
PubMed:The identification of a gene family in the Saccharomyces cerevisiae ergosterol biosynthesis pathway.
PubMed:General resistance to sterol biosynthesis inhibitors in Saccharomyces cerevisiae.
PubMed:Identification of delta 5,7-sterol-delta 7-reductase in higher plant microsomes.
PubMed:Physiological effects of fenpropimorph on wild-type Saccharomyces cerevisiae and fenpropimorph-resistant mutants.
PubMed:Radio-detection high-performance liquid chromatographic enzyme assay for inhibitors of fungal sterol delta 14-reductase.
PubMed:In vivo effects of fenpropimorph on the yeast Saccharomyces cerevisiae and determination of the molecular basis of the antifungal property.
PubMed:Inhibition of microbial cholesterol oxidases by dimethylmorpholines.
PubMed:Cyclopropyl sterol and phospholipid composition of membrane fractions from maize roots treated with fenpropimorph.
PubMed:Effect of some sterol-biosynthesis-inhibiting fungicides on the biosynthesis of polyisoprenoid compounds in barley seedings.
PubMed:Conformational analysis of fenpropimorph.
PubMed:Inhibition by the fungicide fenpropimorph of cholesterol biosynthesis in 3T3 fibroblasts.
PubMed:Sterol biosynthesis via cycloartenol and other biochemical features related to photosynthetic phyla in the amoeba Naegleria lovaniensis and Naegleria gruberi.
PubMed:The action of the systemic fungicides tridemorph and fenpropimorph on sterol biosynthesis by the soil amoeba Acanthamoeba polyphaga.
PubMed:Determination of fenpropimorph in citrus fruit by reversed-phase high-performance liquid chromatography.
PubMed:Ecdysteroid biosynthesis and embryonic development are disturbed in insects (Locusta migratoria) reared on plant diet (Triticum sativum) with a selectively modified sterol profile.
PubMed:Gas chromatographic determination of fenpropimorph residues in citrus fruit.
PubMed:Effect of oxiconazole and Ro 14-4767/002 on sterol pattern in Candida albicans.
 
Notes:
Agricultural fungicide used against powdery mildews on sugar beet, beans and leeks
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