The study investigated the effects of Iprodione on various metabolic processes in Sclerotinia sclerotiorum. The results suggest that the primary mode of action may be related to disruption of nuclear division or DNA-related processes, though a direct molecular target was not identified. The compound did not directly inhibit respiration, major biosynthetic pathways, or cause significant membrane disruption [1].

Iprodione completely inhibited mycelial growth of Sclerotinia sclerotiorum in solid and liquid medium at 3 μM. The ED50 values were 0.6 μM in solid medium and 0.9 μM in liquid medium. At 24 μM, growth of early log phase liquid cultures was completely inhibited within 4 hours, and after 6 hours, mycelial dry weight began to decrease, possibly due to lysis [1].
Iprodione had no significant effect on mycelial respiration. Oxygen consumption was inhibited only 2.5% at 3 μM and 5.8% at 300 μM. No inhibition was detected in early log phase mycelia treated for 2 hours with 24 μM iprodione, whereas 500 μM sodium azide caused 73% reduction within 2 minutes [1].
Uptake of ¹⁴C-labeled substrates (glucose, acetate, glucosamine, uracil, thymine) was only slightly affected by 60 μM Iprodione. Glucose uptake was unaffected over 2 hours; acetate and glucosamine uptake were reduced by 9% and 23% respectively over 4 hours; thymine uptake was reduced by 6-19.5%; uracil uptake was stimulated by 10% [1].
Incorporation of ¹⁴C from glucose into nucleic acids was inhibited within 10 minutes by 3 μM Iprodione (21% inhibition), increasing to 32% inhibition at 3 μM and 65% at 300 μM after 2 hours. The cell pool fraction increased to 120% of control by 1 hour and 171% at 2 hours, suggesting accumulation of precursors [1].
Using specific precursors, DNA incorporation of ¹⁴C from thymine and uracil was inhibited approximately 32%, while RNA incorporation from uracil was inhibited only 15% by 75 μM Iprodione. However, incorporation of ¹⁴C from aspartic acid and glycine (precursors for purine and pyrimidine nucleotide synthesis) into RNA and DNA was not inhibited by 2.4 μM iprodione; in fact, stimulation was observed (191-313% of control), indicating that nucleotide biosynthesis pathways were not directly inhibited [1].
Incorporation of ¹⁴C from glucosamine into cell wall was reduced 20.5% by 30 μM Iprodione, but the glucose/glucosamine ratio remained unchanged. Lipid synthesis from acetate was not significantly affected [1].

Sclerotinia sclerotiorum (ATCC 10940) was maintained on potato-dextrose agar. Liquid shake cultures were grown in glucose peptone medium (50 mL in 250-mL flasks) at 22°C on a gyratory shaker. The medium contained glucose (15 g/L), KH₂PO₄ (2.5 g/L), MgSO₄·7H₂O (0.5 g/L), bacteriological peptone (5 g/L), and minor element concentrates [1].
For growth studies on solid medium, 6-mm diameter plugs from actively growing cultures were placed on PDA plates containing various concentrations of Iprodione (added in acetone, final acetone 0.2%). Colony diameter was measured at 48 hours. For liquid cultures, mycelial dry weight was determined at various time points after adding Iprodione [1].
For respiration studies, mycelia from 36-hour cultures were harvested and suspended in GP medium (10 mg dry weight/mL). Oxygen consumption was measured using a Clark electrode in a Biological Oxygen Monitor [1].
For uptake and incorporation studies, mycelia from 48-hour cultures were collected by vacuum filtration, washed, and suspended in fresh GP medium or 0.1 M potassium phosphate buffer (pH 6.5) at 3 mg dry weight/mL. Iprodione and ¹⁴C-labeled substrates were added simultaneously. For uptake, aliquots were removed at various times, filtered on Teflon filters, washed, and radioactivity measured. For incorporation studies, mycelia were harvested, washed, and fractionated by TCA extraction followed by differential extraction of RNA and DNA by the Schmidt-Thannhauser method. DNA and RNA concentrations were determined by diphenylamine and orcinol methods, respectively [1].
Cell wall components were analyzed by TLC after hydrolysis using solvent systems: n-butanol:glacial acetic acid:water (60:30:10) and n-propanol:ethyl acetate:water:25% ammonia (60:10:30:10). Lipids were extracted and fractionated by TLC with hexane:diethyl ether:glacial acetic acid (70:30:2). Nucleotides from RNA hydrolysates were separated by TLC with 0.1 N HCl [1].

Metabolism/Metabolites
After being absorbed by the roots in plants, they are rapidly metabolized into 3,5-dichloroaniline.

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Toxicity Data
LC50 (Rat) > 3,300 mg/m3

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Non-human Toxicity Values LD50 (Rats, oral): 3500 mg/kg
LD50 (Mice, oral): 4000 mg/kg
LD50 (Rats, dermal): >2500 mg/kg
LD50 (Rabbit, dermal): >2000 mg/kg
For more complete non-human toxicity data for isoproturon (6 in total), please visit the HSDB records page.

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The study focuses on fungicidal activity against B. cinerea. Iprodione at 5 μM caused complete inhibition of radial growth and significant alterations in lipid metabolism. Higher concentrations (10-50 μM) caused greater inhibition of lipid labelling (55-78% reduction) and at 50 μM, acetate uptake was also reduced by 21% after 24 hours, indicating possible general metabolic toxicity at very high concentrations [2].

[1]. The Effects of the Fungicide, Iprodione, on the Mycelium of Sclerotinia sclerotiorum. Phytopathology, 1981, 71(7): 722-727.

[2]. Lipid composition of Botrytis cinerea and inhibition of its radiolabelling by the fungicide iprodione. New Phytol. 2003 Oct;160(1):199-207.

[3]. Effect of iprodione, a dicarboximide fungicide, on primary cultured rainbow trout (Oncorhynchus mykiss) hepatocytes. Aquat Toxicol. 2001 Sep;54(1-2):51-8.

[4]. Iprodione and Chlorpyrifos, Alone and in a Mixture, Impaired Male Fertility and Sexual Behavior in Adult Rats via Suppression of Steroidogenic Genes and SIRT1/TERT/PGC-1α Pathway. 2021.

[5]. Iprodione delays male rat pubertal development, reduces serum testosterone levels, and decreases ex vivo testicular testosterone production. Toxicol Lett. 2007 Nov 1;174(1-3):74-81.

According to the U.S. Environmental Protection Agency (EPA), iprodione may be carcinogenic. Iprodione is an imidazoline-2,4-dione compound, with its nitrogen atom at position 1 replaced by an N-(isopropyl)formamide group and its nitrogen atom at position 3 replaced by a 3,5-dichlorophenyl group. It is a contact fungicide that inhibits the growth of fungal mycelium and the germination of spores. It is used to control various fungal diseases in fruit and vegetable crops and can also be used as a nematicide. It has the dual effects of being a nematicide and an antifungal pesticide. It is an imidazoline-2,4-dione compound, belonging to the urea, benzene, imidazole, and dichlorophenyldicarboximide fungicides. Iprodione is a hydantoin fungicide. It is used to control crops affected by gray mold, brown rot, sclerotinia rot, and other fungal diseases. It is currently used on a variety of crops: fruits, vegetables, ornamental trees and shrubs, and lawns. It is a contact fungicide that inhibits fungal spore germination and blocks fungal mycelial growth.

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Mechanism of Action
Inhibits spore germination and fungal mycelial growth.

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Iprodione [3-(3,5-dichlorophenyl)-N-isopropyl-2,4-dioxoimidazolidine-1-carboximide] is a fungicide particularly effective against Sclerotinia and Botrytis species. It is not phytotoxic to most higher plants and has very low mammalian toxicity. It has potential as an important protectant fungicide for various vegetable and fruit crops [1].
The mechanism of action of Iprodione and its analogues (procymidone, vinclozolin) was not known at the time of this study. Previous studies on other fungi suggested possible effects on DNA biosynthesis, lipid biosynthesis, membrane transport functions, or cell wall synthesis. This study on S. sclerotiorum found that while growth was rapidly inhibited, respiration, uptake of various substrates, and major biosynthetic pathways (nucleotide synthesis, protein synthesis, lipid synthesis) were not directly affected. The rapid inhibition of ¹⁴C incorporation into nucleic acids (within 10 minutes) without direct inhibition of nucleotide biosynthesis, combined with observations from analogue studies showing effects on nuclear division and mitotic instability, suggests that Iprodione may act by disrupting nuclear division or some interaction with the nucleus. Preliminary data mentioned in the study indicates that iprodione selectively binds to proteins, which may relate to its effects on nuclear division [1].

C13H13CL2N3O3

330.17

329.033

36734-19-7

Iprodione-d5;1215631-57-4

37517

White to off-white solid powder

1.5±0.1 g/cm3

481.1±55.0 °C at 760 mmHg

130-134 °C(lit.)

244.7±31.5 °C

0.0±1.3 mmHg at 25°C

1.645

2.22

1

3

2

21

448

0

ONUFESLQCSAYKA-UHFFFAOYSA-N

InChI=1S/C13H13Cl2N3O3/c1-7(2)16-12(20)17-6-11(19)18(13(17)21)10-4-8(14)3-9(15)5-10/h3-5,7H,6H2,1-2H3,(H,16,20)

3-(3,5-dichlorophenyl)-2,4-dioxo-N-propan-2-ylimidazolidine-1-carboxamide

Iprodione Glycophene Glycophen

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ~100 mg/mL (~302.87 mM)

Solubility in Formulation 1: ≥ 2.5 mg/mL (7.57 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

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Solubility in Formulation 2: ≥ 2.5 mg/mL (7.57 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

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 (Please use freshly prepared in vivo formulations for optimal results.)