There is currently no FRAC Working Group on dicarboximides. Instead an informal network of experts around the world has been formed which exists to optimise information exchange on dicarboximide resistance. Requests for information should be addressed either to the Chairperson or directly to individual expert members of the network. A list of experts is provided at the end of this page.

The activity of dicarboximide fungicides was first reported in the early 1970's (Fujinami et al. 1971) with the three key commercial products being introduced within three years; iprodione (Lacroix et al. 1974), vinclozolin (Pommer & Mangold 1975) and procymidone (Hisada et al. 1977). They are typically protectant fungicides and although some claims to systemicity have been made (Hisada et al. 1977) they are best regarded as protectant materials.
Compared to many other classes of fungicide their activity spectrum is relatively narrow, but includes species from the following genera: Botrytis, Sclerotinia, Sclerotium, Monilia, Alternaria, Phoma, Didymella, Rhizoctonia, Laetisaria (Corticium). Current actives on the market are iprodione, vinclozolin and procymidone. They are sold alone and as components of many co-formulated mixtures.

Dicarboximides were originally introduced for control of Botrytis cinerea, primarily on vines where they were welcomed due to the occurrence at the time of resistance to mbc fungicides. Resistance management strategies were poorly understood at the time and this inevitably led to overuse of the products such that resistance developed very quickly. Botrytis remains the main fungus at risk although resistance in other genera can easily be found (Table 1).

Table 1. Fungi resistant to dicarboximides (based on Pommer & Lorenz 1987)

Even after almost 30 years of research the mode of action of dicarboximides is still not certain. Recent evidence (for review see Yamaguchi & Fujimura, 2005) suggests that they interfere with the osmotic signal transduction pathway consisting of histidine kinase and MAP kinase cascades.

In B. cinerea and A. alternata , resistance has been attributed to mutations in the histidine kinase genes (Yamaguchi & Fujimura 2005, Dry et al. 2004, Oshima et al. 2002). Similar evidence that the osmoregulatory system is involved in resistance in Cochliobolus heterostrophus is given by Yoshimi et al. 2003.

Resistant isolates of B cinerea typically show either low, moderate or high levels of resistance according to laboratory assay. Low and moderate levels are normally associated with field isolates, but are still capable of causing disease control failure. Isolates rated as highly resistant in laboratory assay are rarely found in the field.

Cross resistance exists between all dicarboximides although due to differences in activity spectra it may not appear as a perfect relationship with some fungi. In addition, fungi resistant to dicarboximides have been shown to have various levels of resistance to aromatic hydrocarbon fungicides such as chloroneb and tolclofos-methyl, although such cross resistance is not always present. In laboratory conditions some cross resistance to phenylpyrroles has been noted but this phenomenon has not been found in field isolates resistant to dicarboximides.
B. cinerea is a pathogen famous for its ability to become resistant to fungicides. Resistance to benzimidazoles (mbc fungicides) is common and can be easily accompanied by resistance to dicarboximides and to phenylcarbamates (e.g. diethofencarb). Double or triple multiple resistance is thus quite possible and must be considered when choosing disease control programmes that include such chemistry. Please note that resistance to dicarboximides does not make fungi resistant to benzimidazoles or phenylcarbamates i.e. there is no cross resistance between these chemical groups.

As a general guide it is accepted that the more resistant an isolate becomes to a dicarboximide fungicide, the less able it is to compete with non resistant isolates in the wild. However, the picture may not be as definite as suggested: In a study conducted by Fourie and Holz (2003) using isolates of B. cinerea and grapes, both sensitive and resistant germlings colonised fungicide free berries equally well, although sensitive strains penetrated the surface more often. Fitness decreased as resistance increased.
When using laboratory selected strains of Sclerotinia minor isolated from lettuce Hubbard et al. (1997) found that the virulence of resistant strains generated from resistant sclerotia declined with age, occasionally resulting in complete loss of virulence. Similar results were found by Raposo et al . (2000) when looking at B. cinerea from tomatoes grown in glasshouses. Sclerotia of resistant isolates survived less well than sensitive ones. There was no relationship found between survival ability and resistance when mycelial survival was considered.
In contrast LaMondia & Douglas (1997) and Moorman & Lease (1992) report no change in fitness levels of B cinerea isolated from glasshouse crops in the USA . It is thus wise to assume that reduced fitness is not a phenomenon that can be relied upon as a component of a resistance management programme.

• Minimise the selection pressure by minimising the number of applications. As a guide, do not apply more than two to three per crop per season. to be applied.
• Restrict applications to those times when Botrytis infection pressure is high.
• Maintain regular prolonged times without exposure to dicarboximides.
• Where resistance is well established, use combinations to stabilise Botrytis control, but their application must follow the same rules as for dicarboximides alone.

Note that individual countries will now have their own, more detailed, use guidelines for specific crops.

Dry, I. B., Yuan, K. H., Hutton, D. G. (2004) Dicarboximide resistance in field isolates of Alternaria alternata is mediated by a mutation in a two component histidine kinase gene. Fungal Genet Biol 41 , 102 – 108

Fourie, P. H., Holz, G. (2003) Fitness on grape berries of Botrytis cinerea isolates belonging to different dicarboximide sensitivity classes. South African Journal of ecology and viticulture, 24, 1 - 10

Fujinami, A., Ozaki, K., Yamamoto, S. (1971) Studies on biological activity of cyclic amide compounds. Part 1. Antimicrobial activity of 3-phenyloxazolidine-2,4-diones and related compounds. Agric. Biol. Chem 35 , 1707 – 1719

Hisada, Y., Kato, T., Kawase, Y. (1977) Systemic movements in cucumber plants and control of cucumber gray mould by a new fungicide, S-7131. Netherl. J. Plant Pathol. 83, 71 – 78

Hubbard, J. C., Subbarao, K. V., Kolke, S. T., (1997) Development and significance of dicarboximide resistance in Sclerotinia minor isolates from commercial lettuce fields in California . Plant Disease 81, 148 - 153

Lacroix, L., Bic, C., Burgaud, L., Guillot, M., Leblanc, R., Riottot, R., Sauli, M. (1974) Etude des propriétés antifongiques d'une nouvelle famille des dérivés de l'hydantoine et en particulier du 26019 R.P. Phytiatrie-Phytopharmacie 23 , 165 – 174

LaMondia, J. A., Douglas, S. M., (1997) Sensitivity of Botrytis cinerea from Connecticut greenhouses to benzimidazole and dicarboximide fungicides. Plant Disease 81, 729 – 732

Moorman, G. W., Lease, R. J., (1992) Benzimidazole and dicarboximide resistant Botrytis cinerea from Pennsylvania greenhouses. Plant Disease 76, 477 – 480

Oshima, M., Fujimura, M. Banno, S., Hashimoto, C., Motoyama, T., Ichiishi, A., Yamaguchi, I. (2002) A point mutation in the two component histidine kinase BcOS-1 gene confers dicarboximide resistance in field isolates of Botrytis cinerea Phytopathology 92, 75 - 80

Pommer, E-H., Mangold, D. (1975) Vinclozolin (BAS 352F) ein neuer Wirkstoff zur Bekämpfung von Botrytis cinerea. Meded. Fak. Landbouwwet. Rijksuniv. Gent 40 , 713 – 722

Pommer, E-H., Lorenz, G. (1987) Dicarboximide fungicides. In: Modern Selective Fungicides. Ed H Lyr, Gustav Fischer 1987, pp99 – 118.

Raposo, R., Gomez, V., Urrutia, T., Melgarejo, P. (2000) Fitness of Botrytis cinerea associated with dicarboximide resistance. Phytopathology 90, 1246 - 1249

Yamaguchi, I., Fujimura, M. (2005) Recent topics on action mechanisms of fungicides. Journal of Pesticide Science 30, 67 – 74

Yoshimi, A., Imanshi, J., Gafur, A., Tanaka, C., Tsuda, M. (2003) Characterisation and genetic analysis of laboratory mutants of Cochliobolus heterostrophus resistant to dicarboximide and phenylpyrrole fungicides. Journal of General Plant Pathology 69 , 101 – 108