36734-19-7 Usage
Uses
Different sources of media describe the Uses of 36734-19-7 differently. You can refer to the following data:
1. Fungicide.
2. Iprodione is a non-systemic fungicide that exhibits both protectant
and eradicant activities against the spores and mycelium of a number
of parasitic fungi. It is effective against Alternaria, Botrytis, Corticium,
Fusarium, Helminthosporium, Monilinia, Phoma, Pleiochaeta, Rhizoctonia
and Sclerotinia, etc. in nut crops, fruit trees (stone and pome fruit),
vines, berries, vegetables, cereals, oilseed rape, cotton and ornamentals.
Iprodione also controls various summer and winter turf diseases.
Definition
ChEBI: An imidazolidine-2,4-dione in which the nitrogen at position 1 is substituted by an N-(isopropyl)carboxamide group while that at position 3 is substituted by a 3,5-dichlorophenyl group. A contact fungicide, it blocks the growth of the fu
gal mycelium and inhibits the germination of fungal spores. It is used on fruit and vegetable crops affected by various fungal diseases. It is also used as a nematicide.
Safety Profile
Moderately toxic by
ingestion. When heated to decomposition it
emits very toxic fumes of NOx and Cl-.
Environmental Fate
Soil. Readily degrades in soil (half-life 20 to 160 days) releasing carbon dioxide 3,5dichloroaniline (Walker, 1987) and (Hartley and Kidd, 1987; Worthing and Hance, 1991). The rate of degradation increases with repeated applications of this fungicide. In a clay loam, the half-life was 1 week. After the second and third applications, the half-lives were 5 and 2 days, respectively (Walker et al., 1986).Plant. Translocation and uptake by potato plants were reported (Cayley and Hide, 1980). Iprodione is rapidly metabolized in plants to 3,5-dichloroaniline (Cayley and Hide, 1980; Hartley and Kidd, 1987).Chemical/Physical. In an aqueous solution at pH 8.7, iprodione hydrolyzed to N-(3,5dichloroanilinocarbonyl)-N-(isopropylaminocarbonyl)glycine (Belafdal et al., 1986). At pH 8.7, complete hydrolysis occurred after 14 hours (Cayley and Hide, 1980).Gomez et al. (1982) studied the pyrolysis of iprodione in an helium atmosphere at 400–1,000°C. Decomposition began at 300°C producing isopropyl isocyanate and 3-(3,5dichlorophenyl)hydantoin. Above 600°C, the hydantoin ring began to decompose forming the following products: 3-chloroaniline, 3,5-dichloroaniline, chlorinated benzenes and benzonitrile. From 800 to 1,000°C, the hydantoin ring was completed destroyed whichled to the formation of aryl isocyanates, anilines and the corresponding diarylureas, namely 3-(3,5-dichlorophenyl)urea and 1-(3-chlorophenyl)-3-(3,5-dichlorophenyl)urea (Gomez et al., 1982).
Metabolic pathway
The opening and rearrangement of the dioxoimidazolidine ring is the
initial and major degradation/metabolic reaction for iprodione. Iprodione
degrades in soil via cleavage of the dioxoimidazolidine-carboxamide
linkage, followed by ring opening to yield 3,5-dichloroaniline and
CO2. In plants and animals, primary degradation reactions include
N-dealkylation of the isopropyl moiety, ring opening and aryl hydroxylation
(Scheme 1).
Degradation
Iprodione (1) is stable in acidic solution (< pH 5) and degraded rapidly
in alkaline solution with DT50 values of 37 days, 1.1 days and 21 min at
pH 5, 7 and 9 at 25 °C, respectively (Melkebeke et al., 1986). Opening
of the oxazolidinedione ring yielded N-(3,5-dichloroanilinocarbonyl)-N-
(isopropylaminocarbonyl)glycine (2) (Belafdal et al., 1986). This reaction
involves the attack of a hydroxyl ion on the carbonyl moiety in the
4-position of the hydantoin ring. Laurent (1974a, 1976a) and Das (1990)
reported the further dehydration/rearrangement of compound 2 to yield
an iprodione isomer (3).
Iprodione degraded readily in water under UV light irradiation
(Laurent, 197413) but was relatively stable when exposed to simulated
sunlight (Adrian and Robles, 1991). The degradation of iprodione in aqueous
solution proceeded via various mechanisms including isomerisation,
dechlorination, hydrolysis and hydroxylation.
Schwack et al. (1995) and Schwack and Bourgeois (1989) reported that
dechlorination was the primary photodegradation reaction when iprodione
in various organic solvents (e.g. isopropanol) was irradiated with
UV light (>280 nm). Other photodegradation reactions included the
replacement of the chlorine atom by the solvent molecule.
Check Digit Verification of cas no
The CAS Registry Mumber 36734-19-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,6,7,3 and 4 respectively; the second part has 2 digits, 1 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 36734-19:
(7*3)+(6*6)+(5*7)+(4*3)+(3*4)+(2*1)+(1*9)=127
127 % 10 = 7
So 36734-19-7 is a valid CAS Registry Number.
InChI:InChI=1/C15H19N3O3/c1-9(2)16-14(20)17-8-13(19)18(15(17)21)12-6-10(3)5-11(4)7-12/h5-7,9H,8H2,1-4H3,(H,16,20)
36734-19-7Relevant articles and documents
Preparation method of iprodione
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Paragraph 0039-0046; 0050-0057, (2017/10/28)
The invention discloses a preparation method of iprodione, which comprises of mixing N-[[(3,5 dichlorophenyl) amino] carbonyl] glycine with an organic solvent to react by the action of a catalyst A to generate 3-(3,5-dichlorophenyl)-2,4-imidazolidinedione, and allowing 3-(3,5-dichlorophenyl)-2,4-imidazolidinedione to react with isopropyl isocyanate by the action of a catalyst B and a catalyst C to generate iprodione, wherein the catalyst A is a mixture of concentrated sulfuric acid, methanesulfonic acid and p-toluenesulfonic acid; the catalyst B is a mixture of ammonium carbonate, sodium bicarbonate and sodium carbonate; and the catalyst C is a mixture of pyridine and triethylamine. A content of the finished product, namely iprodione prepared by the method reaches above 97%, and the preparation cost of iprodione is greatly lowered.
Pyrimidine derivatives, process and intermediate products for their preparation and pesticides or fungicides containing these derivatives
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, (2008/06/13)
Pyrimidine compounds I wherein X is C(CO2CH3)═NOCH3, C(CONHCH3)═NOCH3, C(CO2CH3)═CHOCH3, C(CO2CH3)═CHCH3or N(CO2CH3)—OCH3; R1, R2are hydrogen, alkyl, haloalkyl or alkoxy; A is R3is hydrogen, alkyl, haloalkyl, phenoxyalkyl, cycloalkyl, cyano, alkoxy, hydroxyl or halogen; R4is hydrogen, optionally substituted alkyl, alkenyl, alkynyl, haloalkenyl, haloalkynyl, cycloalkyl or alkoxy; Y is hydrogen, hydroxyl, halogen, optionally substituted aryl, hetaryl, cycloalkyl, cycloalkenyl, heterocyclyl, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, aryloxy, arylthio, hetaryloxy, hetarylthio, cycloalkyloxy or alkylthio, or their salt, their synthesis and intermediates therefore, and their activity against fungi or animal pests.
Plant-protective pesticidal composition
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, (2008/06/13)
The invention relates to a plant-protective solution containing 2.5 to 40 % by weight of one or more water-insoluble plant-protective ingredient(s) 20 to 71.5 % by weight of dimethylformamide and/or dimethylsulfoxide and/or acetone as water-miscible solvent, 10 to 71.5 % by weight of furfurol and/or furfuryl alcohol as partially water-miscible solvent, 1 to 15 % by weight of commonly used additives such as anionic and/or nonionic surface active agents and macromolecules. The invention also relates to the ready-for-use plant-protective suspension containing 0.2 to 10 % by weight of one or more water-insoluble plant-protective ingredient(s) with a particle size of 0.1 to 50 μm, 0 to 60 % by weight of a fertilizer, 0.2 to 10 % by weight of dimethylformamide and/or dimethylsulfoxide and/or acetone as water-miscible solvent, 0.2 to 10 % by weight of furfurol and/or furfuryl alcohol as partially water-miscible solvent, 0.05 to 2.5 by weight of a commonly used additive such as anionic and/or nonionic surface active agents macromolecules and water in an amount supplementing up to 100 % by weight.