Myclobutanil

SYSTHANE · nova · rh-53,866 · Nove · novaw · rally · Syseant · RH-3866

Identifikatoren & physikalische Daten

CAS No.	88671-89-0
Summenformel	C15H17ClN4
Durchschnittliche Molmasse	288,77 g/mol
Monoisotopische Masse	288,11417422 g/mol
SMILES	CCCCC(C#N)(Cn1cncn1)c1ccc(Cl)cc1
InChIKey	HZJKXKUJVSEEFU-UHFFFAOYSA-N
PubChem CID	6336
ChEMBL	CHEMBL1904430
ChEBI	CHEBI:83729
EC No.	410-400-0
DTXSID	DTXSID8024315

Chemische & physikalische Eigenschaften

XLogP	2,9
Polarare Oberfläche (TPSA)	54,5
H-Brücken-Donoren	0
H-Brücken-Akzeptoren	3
Frei drehbare Bindungen	6
Schwere Atome	20
Formalladung	0
Komplexität	345
Pestizide	PesticidesPesticide -> EPA IRISFungicidesActive substance -> EU Pesticides database: Not approvedPesticides -> FungicidesEnvironmental transformation -> Pesticides (parent, predecessor)
LogP (Verteilungskoeffizient)	log Kow = 2.943.16
Color/Form	Pale yellow solid.Light yellow crystals
Löslichkeit	Soluble in common organic solvents, e.g. ketones, esters, alcohols and aromatic hydrocarbons, all 50 to 100 g/L. Insoluble in aliphatic hydrocarbons.Soluble in ethanol, benzene, ethyl acetate, and acetone.In water, 142 mg/L at 25 °CChloroform (Slightly), DMSO (Slightly), Methanol (Slightly)142 mg/L (25 ºC)
Endocrine Disruptors	Potential endocrine disrupting compound
Siedepunkt	202 to 208 °C at 1 mm Hg202-208°C
Schmelzpunkt	63 to 68 °C63-68°C
Dampfdruck	0.0000016 [mmHg]1.6X10-6 mm Hg at 25 °C2.13 x l0-4 Pa (25 °C)
Physical Description	Myclobutanil is a light yellow solid used as a fungicide.Light yellow solid[Merck Index]
Stability/Shelf Life	Stable under normal storage conditions.Aqueous solutions decompose on exposure to light ...
Ionization Efficiency	Positive2.992.7Agilent XCTElectrospray ionizationformic acid (5.3nM)
Collision Cross Section	174.5 Å² [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: Pesticides]173.77 Å² [M+H]+
Dichte	1.1614 (rough estimate)
Brechungsindex	1.6110 (estimate)
Flammpunkt	>100 °C
Lagerbedingungen	Sealed in dry,2-8°C
Aggregatzustand	Solid
pKa (Säurekonstante)	2.30±0.10(Predicted)
Farbe	White to off-white
Merck	13,6346
BRN	7138849
Henry-Konstante	2.3×103 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
Hauptanwendungen	agriculturecleaning productscosmeticsenvironmentalfood and beveragespersonal care
InChI	1S/C15H17ClN4/c1-2-3-8-15(9-17,10-20-12-18-11-19-20)13-4-6-14(16)7-5-13/h4-7,11-12H,2-3,8,10H2,1H3
InChIKey	HZJKXKUJVSEEFU-UHFFFAOYSA-N
SMILES	CCCCC(Cn1cncn1)(C#N)c2ccc(Cl)cc2
CAS Datenbank	88671-89-0(CAS DataBase Reference)
EPA chemische Informationen	Myclobutanil (88671-89-0)

Sicherheit & Vorschriften

GHS-Einstufung	WarningH302: Harmful if swallowed [Warning Acute toxicity, oral]P203, P264, P264+P265, P270, P273, P280, P301+P317, P305+P351+P338, P318, P330, P337+P317, P391, P405, and P501 (click each P-code to see the statement)H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P260, P264, P264+P265, P270, P273, P280, P301+P317, P305+P351+P338, P318, P319, P330, P337+P317, P391, P405, and P501 (click each P-code to see the statement)
Regulatorische Informationen	Hazard Traits - Developmental ToxicityReproductive ToxicityCommission Regulation (EC) No 1490/2002Myclobutanil is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)2011/2/EU, Reg. (EU) 2018/155, Reg. (EU) 2022/801, Reg. (EU) No 540/2011Status: Active Update: 07-10-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/33152Myclobutanil: HSNO Approval: HSR002866 Approved with controls
DOT-Kennzeichnung	Poison
Brandgefahren	Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:
Gesundheitsgefahren	Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:
Gefahrenübersicht	Target organ in animal studies is the liverA reproductive toxin in rats fed 3.6 mg/kg/day for 2 generations[Reference #1] A corrosive substance that can cause permanent eye damage[HSDB]
Reaktive Gruppe	Amines, Phosphines, and Pyridines
Special Reports	Mineau P et alEcotoxicology and Environmental Safety 29 (3): 304-329 1994. An analysis of avian reproduction studies submitted for pesticide registration.
FIFRA-Anforderungen	Tolerances are established for combined residues of the fungicide myclobutanil alpha-butyl-alpha-(4-chlorophenyl)-1 H -1,2,4-triazole-1-propanenitrile and its alcohol metabolite (alpha-(3-hydroxybutyl)-alpha-(4-chlorophenyl)-1 H -1,2,4-triazole-1-propanenitrile (free and bound), in or on the following food commodities: [Table#6209]

Anwendungen & Verwendung

Beschreibung

Myclobutanil is a broad-spectrum systemic foliar-applied fungicide of the substituted triazole chemical class of compounds, with protective, eradicative, and curative action. It disrupts membrane function in fungi by inhibition of sterol biosynthesis. It is produced by the alkylation of 4-chlorophenylacetonitrile with butyl chloride, followed by treatment with dibromomethane and sodium hydroxide in dimethyl sulfoxide. The resulting intermediate is then reacted with the potassium salt of 1,2,4-triazole in dimethyl formamide. Commercially, myclobutanil is presented as different formulations or preparations with concentrations up to 60% active ingredient (a.i.). It is formulated as a wettable powder (2–40% a.i.) or as an emulsifiable concentrate (1–25% a.i.), granular ( It is also used at lower concentrations in combination with other agrochemicals such as pyretroids (permethrin), fludioxonil, mefenoxam, azoxistrobin, mancozeb, sulfur, or fluoxastrobin.

Verwenden

Myclobutanil is an fungicide used on a wide range of food crops. Myclobutanil inhibits the biosynthesis of ergosterol, a critical componet of fungal cell membranes.