133-07-3 Usage
Uses
Used in Agriculture:
Folpet is used as an agricultural fungicide for controlling downy mildews, powdery mildews, leaf spot diseases, scab, and rots in fruit, ornamentals, and vegetables. It is particularly effective against cherry leaf spot, rose mildew, rose black spot, and apple scab.
Used in Horticulture:
Folpet is used on berries, flowers, ornamentals, fruits, and vegetables, as well as for seed and plant-bed treatment, providing protection against various fungal diseases.
Used in Paints and Plastics Industry:
Folpet is used as a fungicide in paints and plastics, helping to prevent fungal growth on these materials.
Used in Building Industry:
Folpet is also used for the treatment of internal and external structural surfaces of buildings to protect against fungal infestations.
Occupational Exposure:
Occupational exposure to Folpet mostly occurs in agricultural workers or florists, as they handle the fungicide during its application in various settings.
Air & Water Reactions
Insoluble in water. Hydrolyzed in alkaline solution. Hydrolysis products are corrosive to many metals.
Reactivity Profile
A halogenated phthalimide.
Contact allergens
Folpet is a pesticide, fungicide agent of thiophthalim ide group. Occupational exposure occurs mostly in
agricultural workers or in florists. Photosensitivity has
been reported.
Safety Profile
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.
Metabolic pathway
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.
Check Digit Verification of cas no
The CAS Registry Mumber 133-07-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,3 and 3 respectively; the second part has 2 digits, 0 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 133-07:
(5*1)+(4*3)+(3*3)+(2*0)+(1*7)=33
33 % 10 = 3
So 133-07-3 is a valid CAS Registry Number.
InChI:InChI=1/C9H4Cl3NO2S/c10-9(11,12)16-13-7(14)5-3-1-2-4-6(5)8(13)15/h1-4H
133-07-3Relevant articles and documents
2-Trichloromethylthio-1H-isoindole-1,3(2H)-dione (Folpet)
Carle, A. Bjoern,Krause Bauer, Jeanette A.,Wilson, R. Marshall
, p. 97 - 98 (2000)
The title compound (C9H4Cl3NO2S), commonly known as Folpet, belongs to a group of phthalimides which function as fungicides or can be used in the laboratory as sulfurizing agents. The phthalimide moiety is sligh
A FUNGICIDAL COMPOUND AND PROCESS OF PREPARATION THEREOF
-
Page/Page column 23-24, (2021/11/06)
The present invention relates to a fungicidal sulfenyl phthalimide compound of formula (I) and a compound of formula (II) wherein said compound of formula (I) and formula (II) are substantially free from unwanted impurity. Particularly the present invention relates to a process of preparation of compounds of formula (I) and (II) substantially free from unwanted impurity.
Protective agents for wood
-
, (2008/06/13)
Solvent-free coating materials and treating agents used as water-based wood or material protective agents containing emulsifiable binding agents, quaternary ammonium compounds and optional additional active agents. The wood or material protective agents are non-flammable and enable a uniform distribution of the binding agent and the quaternary ammonium compounds in the substrates. As a result, the quaternary ammonium compounds function as a dissolving mediator for the binding agents which are dispersed in water without opacifying effects and are used as a biocide. The agents can additionally absorb water-insoluble organic biocides without impairing the homogeneity or stability of the formulation of the homogeneity of the distribution in the substrate.
Wood preservatives
-
, (2008/06/13)
Wood preservatives having biocidal properties which include quaternary ammonium compounds of general formula (I): wherein R1 is a C8-18-alkyl group or an optionally substituted benzyl group, R2 is a C8-18-alkyl group, R3 is a C1-4-alkyl group or a group of the formula —[CH2—CH2—O]n—H, R4 is a C1-4-alkyl group, n is a number from 0.5 to 8, preferably from 1 to 5, and A?is the anion of an organic carboxylic acid which contains 2 to 12 C atoms and carries at least one hydroxyl, amino or sulfonic acid group. The wood preservatives also penetrate deeply into the wood without the use of pressure, and have only a mild corrosive action on metals. Furthermore, a process for treating timbers with these compositions, concentrates for the preparation thereof, the use of new and known quaternary ammonium compounds in wood preservatives and new quaternary ammonium compounds and their use as biocides.
Use of phosphoric esters as crystallization inhibitors
-
, (2008/06/13)
A new process for preventing the crystallization of certain azole derivatives in the spray equipment upon spraying mixtures containing A) certain azole derivatives which have a tendency to crystallize and B) if appropriate one or more other active compounds and additives, which process comprises adding at least one phosphoric ester of the formula STR1 in which R1 represents alkyl having 2 to 18 carbon atoms and R2 and R3 independently of one another represent alkyl having 2 to 12 carbon atoms, to the spray mixture before spraying.
Fungicidal composition for seed dressing
-
, (2008/06/13)
The present invention relates to a fungicidal composition intended for the protection of the multiplication products of cultivated plants, containing: (a) 2-(4-chlorobenzylidene)-5,5-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)-1-cyclopentanol; (b) one or more fungicides suitable for the protection of the said multiplication products, optionally one or more insecticides, (c), an agriculturally acceptable inert vehicle and an agriculturally acceptable surfactant. The invention also relates to a method for protecting the multiplication products of plants against fungal diseases using these compositions.
Six-membered heterocyclic derivatives of N'-substituted N,N'-diacylhydrazines
-
, (2008/06/13)
This invention relates to insecticidal compositions containing six-membered heterocyclic derivatives of N'-substituted-N,N'-diacylhydrazines, methods of using such compositions and novel six-membered heterocyclic derivatives of N'-substituted-N,N'-diacylhydrazines.
Solid formulations
-
, (2008/06/13)
New solid formulations of A) at least one agrochemical active compound, B) at least one additive from the groups mentioned in the description, C) at least one dispersant, D) at least one carrier and E) if appropriate, further active compounds and/or additives, a process for preparing the solid formulations and their use for treating plants. A new device for preparing new granules.
Preservative for aqueous products and systems
-
, (2008/06/13)
An antimicrobial composition for preserving products or systems containing an aqueous phase comprising from 10 to 60% by weight or tert.-butyl hydroperoxide, from 3 to 50% by weight of a monophenylglycol ether of formulas I or II herein, and the remainder a diluent which is water, an organic solvent or a mixture of water and organic solvent; and a method of use of the antimicrobial composition. The antimicrobial composition may additionally include up to about 20% by weight of a biocide selected from certain non-halogenated phenols, certain heterocyclic compounds and guanidine, phthalimide and urea derivatives.
Insecticidal N'-substituted-N,N'-diacylhydrazines
-
, (2008/06/13)
This invention relates to insecticidal compositions containing N'-substituted-N,N'-diacylhydrazines, methods of using such compositions and certain novel insecticidal N'-substituted-N,N'-diacylhydrazines.
