N-(Trichlormethylthio)phthalimid

Bezeichnung:N-(Trichlormethylthio)phthalimid

CAS-Nr133-07-3

Englisch Name:Folpet

CBNumberCB7377839

SummenformelC9H4Cl3NO2S

Molgewicht296.56

MOL-Datei133-07-3.mol

Synonyma

N-(Trichlormethylthio)phthalimid

2-{(Trichlormethyl)thio}-1H-isoindol-1,3(2H)-dion

N-(Trichlormethylthio)phthalimid physikalisch-chemischer Eigenschaften

Schmelzpunkt	177-180°C
Siedepunkt	333.8±52.0 °C(Predicted)
Dichte	1.5097 (rough estimate)
Dampfdruck	2.1 x 10^-5 Pa (25 °C)
Brechungsindex	1.6000 (estimate)
storage temp.	0-6°C
Löslichkeit	Chloroform (Slightly), Methanol (Slightly)
pka	-3.34±0.20(Predicted)
Farbe	Crystals
Wasserlöslichkeit	practically insoluble
Merck	13,4250
BRN	193373
LogP	2.850
CAS Datenbank	133-07-3(CAS DataBase Reference)
NIST chemische Informationen	Folpet(133-07-3)
EPA chemische Informationen	Folpet (133-07-3)

Sicherheit

Kennzeichnung gefährlicher	Xn,N
R-Sätze:	20-36-40-43-50
S-Sätze:	36/37-46-61
RIDADR	UN 3077 9/PG 3
WGK Germany	2
RTECS-Nr.	TI5685000
HazardClass	9
PackingGroup	III
HS Code	29309090
Giftige Stoffe Daten	133-07-3(Hazardous Substances Data)
Toxizität	LD50 orally in adult male, female rats: >5000 mg/kg (Gaines, Linder)

Gefahreninformationscode (GHS)

Folpet Chemische Eigenschaften,Einsatz,Produktion Methoden

ERSCHEINUNGSBILD
WEISSE KRISTALLE.
CHEMISCHE GEFAHREN
Zersetzung beim Erhitzen oder Verbrennen unter Bildung giftiger und ätzender Rauche mit Schwefeloxiden, Stickstoffoxiden, Chlorwasserstoff (s.ICSC 0163).
ARBEITSPLATZGRENZWERTE
TLV nicht festgelegt (ACGIH 2005).
MAK nicht festgelegt (DFG 2005).
AUFNAHMEWEGE
Aufnahme in den Körper durch Inhalation und über die Haut.
INHALATIONSGEFAHREN
Verdampfung bei 20°C vernachlässigbar; eine gesundheitsschädliche Partikelkonzentration in der Luft kann jedoch beim Versprühen oder Dispergieren schnell erreicht werden, besonders als Pulver.
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION:
Die Substanz reizt die Augen.
WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION
Wiederholter oder andauernder Hautkontakt kann zu Dermatitis und Hautsensibilisierung führen. In Tierversuchen wurden Tumore beobachtet. Die Bedeutung für den Menschen ist nicht bekannt.
LECKAGE
NICHT in die Kanalisation spülen. NICHT in die Umwelt gelangen lassen. Verschüttetes Material in abdichtbaren Behältern sammeln; falls erforderlich durch Anfeuchten Staubentwicklung verhindern. Reste sorgfältig sammeln. An sicheren Ort bringen. Persönliche Schutzausrüstung: Atemschutzgerät, P2-Filter für schädliche Partikel.
R-Sätze Betriebsanweisung:
R20:Gesundheitsschädlich beim Einatmen.
R36:Reizt die Augen.
R40:Verdacht auf krebserzeugende Wirkung.
R43:Sensibilisierung durch Hautkontakt möglich.
R50:Sehr giftig für Wasserorganismen.
S-Sätze Betriebsanweisung:
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S46:Bei Verschlucken sofort ärztlichen Rat einholen und Verpackung oder Etikett vorzeigen.
S61:Freisetzung in die Umwelt vermeiden. Besondere Anweisungen einholen/Sicherheitsdatenblatt zu Rate ziehen.
Beschreibung
Folpet is practically insoluble in water. It is a protective leaf fungicide. Its mode of action inhibits normal cell division of a broad spectrum of microorganisms. It is used to control cherry leaf spot, rose mildew, rose black spot, and apple scab. It is used on berries, flowers, ornamentals, fruits, and vegetables and for seedand plant-bed treatment. It is also used as a fungicide in paints and plastics and for treatment of internal and external structural surfaces of buildings. It is incompatible with strongly alkaline preparations, such as lime sulphur.
Chemische Eigenschaften
Off-White to Pale Yellow Solid
Verwenden
Folpet is a pesticide, fungicide agent from the thiophtalimide group. Occupational exposure occurs mostly in agricultural workers or in florists.
Verwenden
Agricultural fungicide.
Verwenden
Folpet is used to control downy mildews, powdery mildews, leaf spot diseases, scab and rots in fruit, ornamentals and vegetables.
Definition
ChEBI: A member of the class of phthalimides that is phthalimide in which the hydrogen attached to the nitrogen is replaced by a trichloromethylthio group. An agricultural fungicide, it has been used to control mildew, leaf spot, and other diseases in crops sice he 1950s.
Allgemeine Beschreibung
White crystals. Used as a fungicide. Insoluble in water.
Air & Water Reaktionen
Insoluble in water. Hydrolyzed in alkaline solution. Hydrolysis products are corrosive to many metals.
Reaktivität anzeigen
A halogenated phthalimide.
Kontakt-Allergie
Folpet is a pesticide, fungicide agent of thiophthalim ide group. Occupational exposure occurs mostly in agricultural workers or in florists. Photosensitivity has been reported.
Sicherheitsprofil
Moderately toxic by ingestion. Questionable carcinogen with experimental tumorigenic and teratogenic data. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits very toxic fumes of Cl-, NOx, and SOx. Used as a fungicide.
Carcinogenicity
An NCI bioassay of technicalgrade captan was conducted to determine carcinogenicity by administering captan in the feed to Osborne–Mendel rats and B6C3F1 mice. The major outcome was that tumors of the duodenum of B6C3F1 mice were associated with the captan treatment. There was no evidence that the tumors observed in Osborne–Mendel rats were treatment-related.
In the NCI study, groups of 50 rats of each sex were fed average doses of 2520 or 6050 ppm captan in the diet for 80 weeks. Groups of 50 mice of each sex were fed 8000 or 16,000 ppm captan in the diet for 80 weeks. These doses are approximately 250 (male) and 450 (female) mg/kg/day (high dose) and 50 (male) to 100 (female) mg/kg/day (low dose) in rats. In mice, these doses are approximately 2100 mg/kg/day (high dose) and 1000 mg/kg/day (low dose).
Environmental Fate
Folpet rapidly degrades in both aquatic and terrestrial environments, with a reported half-life ranging from 2.6 h to 2 days. The dissipation of folpet in the environment is considered to be dependent on its hydrolysis in water and on microbial-mediated degradation. Its rate of hydrolysis is greatly influenced by pH, with more rapid hydrolysis observed at higher, more alkaline pH levels.
Stoffwechselwegen
Folpet contains an unstable trichloromethylthio (sulfenyl) moiety that has been shown to undergo rapid hydrolytic and metabolic degradation to phthalimide (2). By analogy with captan, presumably the trichloromethylthio moiety can be transferred to the sulfur atoms of thiols such as cysteine and glutathione. Thus in the presence of thiols such as glutathione, folpet is probably cleaved at the N-S bond to form thiophosgene (3) and other gaseous products such as hydrogen sulfide, hydrogen chloride and carbonyl sulfide. Thiophosgene (3) is rapidly hydrolysed by water. The trichloromethylthio group and thiophosgene are believed to be intermediates in the formation of thiazolidine-2-thione-4-carboxylica cid (4) which is an addition product with cysteine. A thiazolidine derivative of glutathione may also be formed (5). Folpet is metabolised in plants and animals to phthalimide (2) and further to phthalamic acid (6) and phthalic acid (7) (see Scheme 1).
Degradation
Folpet is hydrolysed rapidly in strongly alkaline conditions (PM). The hydrolytic DT₅₀ of folpet is 1.1 hours at pH 7. The half-life for hydrolysis of folpet in a commercial formulation was 12 hours at pH 7.35. Folpet was decomposed in dilute, aqueous sulfuric acid with a half-life 10.5 hours at pH 3. The products were mainly phthalimide (2) and small amounts of phthalamic acid (6) and phthalic acid (7). Phthalamic acid (6) had completely degraded by the time all of the folpet had decomposed (Cabras et al., 1997).
Folpet reacts with thiols in two steps. Firstly, phthalimide (2), thiophosgene (3), hydrochloric acid and the corresponding disulfide are produced. Secondly, depending on the thiol, thiophosgene (3) can react with any remaining thiols to give trithiocarbonates, thiurams, etc. In some cases as, for example, with L-cysteine, thiophosgene (3) combines with amino and thiol groups of the reactant yielding the cyclic 2- thiazolidinethiones (4) (Davidek and Seifert, 1975). Folpet reacts with reduced glutathione (GSH) to produce mainly oxidised glutathione (GSSG). Five unidentified products contained all or a portion of the trichloromethyl moiety. Gaseous products including carbonyl sulfide were released (Siegel, 1970).
Toxicity evaluation
Both folpet and its reactive metabolite, thiophosgene, interact with thiol groups and denature proteins. This reaction is responsible for its fungicidal/biocidal activity and its cellular toxicity in mammals. Due to the toxicokinetics of this degradation, folpet toxicity in mammals is generally limited to local irritation effects at the site of contact.

Folpet Upstream-Materialien And Downstream Produkte

N-(Trichlormethylthio)phthalimid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

133-07-3, Folpet Verwandte Suche:

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