Bupirimate

Last updated
Bupirimate
Bupirimate.svg
Names
IUPAC name
5-Butyl-2-ethylamino-6-methylpyrimidin-4-yldimethylsulphamate
Other names
Nimrod, Roseclear 2
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.050.339
EC Number
  • 255-391-2
PubChem CID
Properties
C13H24N4O3S
Molar mass 316.42 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Bupirimate (systematic name 5-butyl-2-ethylamino-6-methylpyrimidin-4-yldimethylsulphamate; brand names Nimrod and Roseclear 2) is an active ingredient of plant protection products (or pesticides), which has an effect as a fungicide. [1] It belongs to the chemical family of pyrimidines. Bupirimate has translaminar mobility and systemic translocation in the xylem. It acts mainly by inhibiting sporulation and is used for control of powdery mildew of apples, pears, stone fruit, cucurbits, roses and other ornamentals, strawberries, gooseberries, currants, raspberries, hops, beets and other crops. Bupirimate is not an insecticide. It is of low mammalian toxicity and is non-toxic to bees. However, it is used in many products which also contain insecticides.

Contents

History

A research programme at ICI's Jealott's Hill site during the 1960s had the objective of discovering fungicides which could penetrate into and move within plants and hence could cure established infections. The outcome of the research was three related compounds: dimethirimol, ethirimol and bupirimate which were first marketed in 1968, 1970 and 1975 respectively. The key target for these fungicides are the mildews but each compound differs in its effect on individual mildew species. In particular, bupirimate is effective on apple powdery mildew caused by the fungus Podosphaera leucotricha , which the earlier materials were not. [2]

Regulation

In terms of the regulation of plant protection products in the European Union, this active substance is in revision of the inclusion in Annex I of the 91/414/EEC Directive. [3] In France, the active substance is permitted in the composition of preparations with an authorization on the market.

Related Research Articles

Pesticide Substance used to destroy pests

Pesticides are substances that are meant to control pests, including weeds. The term pesticide includes all of the following: herbicide, insecticides nematicide, molluscicide, piscicide, avicide, rodenticide, bactericide, insect repellent, animal repellent, antimicrobial, and fungicide. The most common of these are herbicides which account for approximately 80% of all pesticide use. Most pesticides are intended to serve as plant protection products, which in general, protect plants from weeds, fungi, or insects.

A biocide is defined in the European legislation as a chemical substance or microorganism intended to destroy, deter, render harmless, or exert a controlling effect on any harmful organism. The US Environmental Protection Agency (EPA) uses a slightly different definition for biocides as "a diverse group of poisonous substances including preservatives, insecticides, disinfectants, and pesticides used for the control of organisms that are harmful to human or animal health or that cause damage to natural or manufactured products". When compared, the two definitions roughly imply the same, although the US EPA definition includes plant protection products and some veterinary medicines.

Fungicides are biocidal chemical compounds or biological organisms used to kill parasitic fungi or their spores. A fungistatic inhibits their growth. Fungi can cause serious damage in agriculture, resulting in critical losses of yield, quality, and profit. Fungicides are used both in agriculture and to fight fungal infections in animals. Chemicals used to control oomycetes, which are not fungi, are also referred to as fungicides, as oomycetes use the same mechanisms as fungi to infect plants.

Powdery mildew Fungal plant disease

Powdery mildew is a fungal disease that affects a wide range of plants. Powdery mildew diseases are caused by many different species of fungi in the order Erysiphales, with Podosphaera xanthii being the most commonly reported cause. Erysiphe cichoracearum was formerly reported to be the primary causal organism throughout most of the world. Powdery mildew is one of the easier plant diseases to identify, as its symptoms are quite distinctive. Infected plants display white powdery spots on the leaves and stems. The lower leaves are the most affected, but the mildew can appear on any above-ground part of the plant. As the disease progresses, the spots get larger and denser as large numbers of asexual spores are formed, and the mildew may spread up and down the length of the plant.

VG (nerve agent) chemical compound

VG is a "V-series" nerve agent chemically similar to the better-known VX nerve agent. Tetram is the common Russian name for the substance. Amiton was the trade name for the substance when it was marketed as an insecticide by ICI in the mid-1950s.

Biopesticides, a contraction of 'biological pesticides', include several types of pest management intervention: through predatory, parasitic, or chemical relationships. The term has been associated historically with [biological control] – and by implication – the manipulation of living organisms. Regulatory positions can be influenced by public perceptions, thus:

Lead hydrogen arsenate chemical compound

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Diquat chemical compound

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Azoxystrobin chemical compound

Azoxystrobin is the ISO common name for an organic compound that is used as a pesticide. It is a broad spectrum systemic fungicide widely used in agriculture to protect crops from fungal diseases. It was first marketed in 1996 using the brand name Amistar and by 1999 it had been registered in 48 countries on more than 50 crops. In the year 2000 it was announced that it had been granted UK Millennium product status.

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Cyhalothrin group of stereoisomers

Cyhalothrin is the ISO common name for an organic compound that, in specific isomeric forms, is used as a pesticide. It is a pyrethroid, a class of synthetic insecticides that mimic the structure and properties of the naturally occurring insecticide pyrethrin which is present in the flowers of Chrysanthemum cinerariifolium. Pyrethroids such as cyhalothrin are often preferred as an active ingredient in agricultural insecticides because they are more cost-effective and longer acting than natural pyrethrins. λ-and γ-cyhalothrin are now used to control insects and spider mites in crops including cotton, cereals, potatoes and vegetables.

Pirimiphos-methyl chemical compound

Pirimiphos-methyl, marketed as Actellic, and Sybol is a phosphorothioate used as an insecticide. It was originally developed by Imperial Chemical Industries Ltd., now Syngenta, at their Jealott's Hill site and first marketed in 1977, ten years after its discovery.

Tefluthrin Synthetic pyrethroid used as insecticide

Tefluthrin is the ISO common name for an organic compound that is used as a pesticide. It is a pyrethroid, a class of synthetic insecticides that mimic the structure and properties of the naturally occurring insecticide pyrethrin which is present in the flowers of Chrysanthemum cinerariifolium. Pyrethroids such as tefluthrin are often preferred as active ingredients in agricultural insecticides because they are more cost-effective and longer acting than natural pyrethrins. It is effective against soil pests because it can move as a vapour without irreversibly binding to soil particles: in this respect it differs from most other pyrethroids.

Pyrazophos chemical compound

Pyrazophos is an organic compound used as a fungicide and an insecticide.

Fenarimol chemical compound

Fenarimol, sold under the tradenames Bloc, Rimidin and Rubigan, is a fungicide which acts against rusts, blackspot and mildew fungi. It is used on ornamental plants, trees, lawns, tomatoes, peppers, eggplants, cucumbers and melons. It is mainly used to control powdery mildew. It works by inhibiting the fungus's biosynthesis of important steroid molecules.

Early twenty-first century pesticide research has focused on developing molecules that combine low use rates and that are more selective, safer, resistance-breaking and cost-effective. Obstacles include increasing pesticide resistance and an increasingly stringent regulatory environment.

Fluxapyroxad chemical compound

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Cyproconazole chemical compound

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References

  1. U.S. Patent 5,212,197
  2. Bent, K.J.; et al. (1978). "Chapter 10: Pyrimidine fungicides". In Peacock, F.C. (ed.). Jealott's Hill: Fifty years of Agricultural Research 1928-1978 . Imperial Chemical Industries Ltd. pp.  87–97. ISBN   0901747017.
  3. "Bupirimate" (PDF). European Chemicals Agency.