36734-19-7

Usage

Uses

Used in Agriculture:
Iprodione is used as a non-systemic fungicide for protecting and eradicating spores and mycelium of various parasitic fungi. It is effective against Alternaria, Botrytis, Corticium, Fusarium, Helminthosporium, Monilinia, Phoma, Pleiochaeta, Rhizoctonia, and Sclerotinia, among others. It is applied in nut crops, fruit trees (stone and pome fruit), vines, berries, vegetables, cereals, oilseed rape, cotton, and ornamentals.
Additionally, Iprodione is used as a fungicide to control various summer and winter turf diseases, ensuring the health and appearance of lawns and turf areas.

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.

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)

Upstream product

• 64952-42-7 3-(isopropylcarbamoyl)-5-(3,5-dichlorophenyl)hydantoic acid 
• 62584-33-2 3-(3,5-dichloro-phenyl)-ureidoacetic acid 
• 1795-48-8 Isopropyl isocyanate 
• 27387-87-7 3-(3',5'-Dichlorophenyl)imidazolidine-2,4-dione 

Downstream Products

• 62584-33-2 3-(3,5-dichloro-phenyl)-ureidoacetic acid 
• 75-31-0 isopropylamine 
• 626-43-7 3,5-Dichloroaniline 
• 27387-87-7 3-(3',5'-Dichlorophenyl)imidazolidine-2,4-dione 
• 63637-89-8 N-(3,5-dichlorophenyl)-3-(1-methylethyl)-2,4-dioxo-1-imidazolidinecarboxamide 
• 64952-42-7 3-(isopropylcarbamoyl)-5-(3,5-dichlorophenyl)hydantoic acid 

Relevant academic research and scientific papers

Preparation method of iprodione

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.

Broadcast carriers for pesticides and their use

This invention relates to certain natural diatomaceous earth granule compositions which can be broadcast, i. e., dry spread on the soil to deliver a pesticide or fertilizer. The granules retain their physical integrity when spread, and have the unique property to spontaneously disintegrate when irrigation water is applied or rainfall hits the particle. Upon wetting, the particle disintegrates (blooms) to cover the soil surface. This bloom can cover an area many times the original area covered by the granule. The granules have high loadings of the diatomaceous earth, i.e. from about 35 to about 95 weight percent and contain from about 5 to about 40 weight percent of a surfactant system which exhibits excellent disintegration; rewetting and binding properties. Bioactive compounds can be loaded at up to 60 weight percent of the granule. Bioactive compounds may be formulated products or technical grades and may be homogeneously distributed throughout the granule or spray impregnated onto the granule.

Pyrimidine derivatives, process and intermediate products for their preparation and pesticides or fungicides containing these derivatives

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.

Fungicidal composition for seed dressing

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.

Plant-protective pesticidal composition

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.

Kinetics and Mechanisms of Cyclization in Acidic Media of N-N-glycine to Hydantoins: Iprodione and Its Isomer

N--N-glycine (1) cyclizes quantitatively and irreversibly at 50 deg C in the pH range 0.5-6 by two parallel paths to give iprodione (2) and its isomer 3.Formation of the antifungal agent 2 is characterized by a general base catalysis with carboxylate anions, water, and hydroxide ion (β = 0.38) and a solvent isotope effect of 2.90.These results are consistent with a specific base catalyzed addition of the enolate anion of the ureido group to the carboxylic function of hydantoic acid (pKa1 = 4.25) to givetetrahedral intermediate T- whose general acid catalyzed decomposition is rate limiting.Formation of isomer 3 occurs by a specific base catalyzed cyclization of 1 compatible with a nucleophilic attack of the enolate anion of the ureido moiety on the carboxylic group in the pH range 2-6.Below pH 2 hydantoic acid undergoes a specific acid catalysed and spontaneous hydrolysis involving a nucleophilic attack of the ureido enol on the carboxylic function, protonated or not, respectively.Formation of iprodione is general base catalysed while that of its isomer is not: this can be explained by the change in basicity of the leaving groups from the tetrahedral intermediate, i.e., the N- (pKa2 = 11.7) and the N-isopropylureido (pKa3 ca. 18) anions, respectively.

Process for the preparation of 1-carbamoyl-3-(3,5-dichlorophenyl)-hydantoins

1. Process for the manufacture of N-substituted 1-carbamoyl-3-(3,5-dichlorophenyl)-hydantoins of the formula: STR1 in which R1 =alkyl (C1 -C4) or phenyl and R2 =H or alkyl (C1 -C4). 2. This process comprises two steps: a. reacting phosgene with 3-(3,5-dichlorophenyl)-hydantoin in an inert organic solvent medium, in the presence of an acid acceptor, in order to form 1-chlorocarbonyl-3-(3,5-dichlorophenyl)-hydantoin, and b. reacting the chlorocarbonyl formed with an amine HNR1 R2 in an inert organic solvent, in the presence of an acid acceptor. 3. This process makes it possible to obtain the products I, which can be used as agricultural fungicides, with good yields.

Process for the preparation of 1-carbamoyl-3-(3,5-dichlorophenyl)-hydantoins

Fungicidal 1-carbamoyl-3-(3,5-dichlorophenyl)-hydantoins are prepared by reacting 3 mols an isocyanate of the general formula R -- N = C = 0 (wherein R is alkyl of 1-4 carbons or alkenyl of 2-4 carbons) with one mol of 3-(3,5-dichlorophenyl)-ureidoacetic acid in an anhydrous medium in the presence of an organic base.