Fluopicolide

Last updated
Fluopicolide
Fluopicolide structure.svg
Names
Preferred IUPAC name
2,6-Dichloro-N-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]methyl}benzamide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.110.208 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C14H8Cl3F3N2O/c15-8-2-1-3-9(16)12(8)13(23)22-6-11-10(17)4-7(5-21-11)14(18,19)20/h1-5H,6H2,(H,22,23)
    Key: GBOYJIHYACSLGN-UHFFFAOYSA-N
  • InChI=1/C14H8Cl3F3N2O/c15-8-2-1-3-9(16)12(8)13(23)22-6-11-10(17)4-7(5-21-11)14(18,19)20/h1-5H,6H2,(H,22,23)
    Key: GBOYJIHYACSLGN-UHFFFAOYAE
  • C1=CC(=C(C(=C1)Cl)C(=O)NCC2=C(C=C(C=N2)C(F)(F)F)Cl)Cl
Properties
C14H8Cl3F3N2O
Molar mass 383.58 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Fluopicolide is a fungicide used in agriculture to control diseases caused by oomycetes such as late blight of potato. It is classed as an acylpicolide and its chemical name is 2,6-dichloro-N-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]methyl}benzamide. [1] The precise mode of action is not known, but it is thought to act by affecting spectrin-like proteins in the cytoskeleton of oomycetes. [1] [2] This mode of action differs from other available fungicides used to control oomycetes and it can inhibit the growth of strains that are resistant to phenylamides, strobilurin, dimethomorph and iprovalicarb. [1] It has some systemic activity as it moves through the xylem towards the tips of stems, but does not get transported to the roots. [2] It affects the motility of zoospores, the germination of cysts, the growth of the mycelium and sporulation. [3] Bayer CropScience developed the compound and it was first released as a commercial product in 2006. [4]

Contents

Uses

Fluopicolide has been shown to be effective at controlling Phytophthora infestans , Phytophthora capsicii , Phytophthora porri , Plasmopara viticola , Perenospora parasitica , Peronospora tabacina , Peronospora sparsa , Pseudoperonospora cubensis and Bremia lactucae . As of 2007, it was only available commercially as a co-formulation with Fosetyl-Al for use in vines (as Profiler) and as a co-formulation with propamocarb for use on potatoes and vegetables (as Infinito). Other products were in development. [5]

Toxicity

The median lethal dose in rats is >5000 mg/kg meaning that fluopicolide has low acute toxicity. [2] [5] Tests in other mammals indicate that it does not cause skin sensitisation, cancer or developmental problems. [5]

Related Research Articles

<span class="mw-page-title-main">Plant pathology</span> Scientific study of plant diseases

Plant pathology is the scientific study of diseases in plants caused by pathogens and environmental conditions. Organisms that cause infectious disease include fungi, oomycetes, bacteria, viruses, viroids, virus-like organisms, phytoplasmas, protozoa, nematodes and parasitic plants. Not included are ectoparasites like insects, mites, vertebrate, or other pests that affect plant health by eating plant tissues. Plant pathology also involves the study of pathogen identification, disease etiology, disease cycles, economic impact, plant disease epidemiology, plant disease resistance, how plant diseases affect humans and animals, pathosystem genetics, and management of plant diseases.

<i>Phytophthora infestans</i> Species of single-celled organism

Phytophthora infestans is an oomycete or water mold, a fungus-like microorganism that causes the serious potato and tomato disease known as late blight or potato blight. Early blight, caused by Alternaria solani, is also often called "potato blight". Late blight was a major culprit in the 1840s European, the 1845–1852 Irish, and the 1846 Highland potato famines. The organism can also infect some other members of the Solanaceae. The pathogen is favored by moist, cool environments: sporulation is optimal at 12–18 °C (54–64 °F) in water-saturated or nearly saturated environments, and zoospore production is favored at temperatures below 15 °C (59 °F). Lesion growth rates are typically optimal at a slightly warmer temperature range of 20 to 24 °C.

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. Fungicides can either be contact, translaminar or systemic. Contact fungicides are not taken up into the plant tissue and protect only the plant where the spray is deposited. Translaminar fungicides redistribute the fungicide from the upper, sprayed leaf surface to the lower, unsprayed surface. Systemic fungicides are taken up and redistributed through the xylem vessels. Few fungicides move to all parts of a plant. Some are locally systemic, and some move upward.

<span class="mw-page-title-main">Downy mildew</span> Name for several species of fungus

Downy mildew refers to any of several types of oomycete microbes that are obligate parasites of plants. Downy mildews exclusively belong to the Peronosporaceae family. In commercial agriculture, they are a particular problem for growers of crucifers, grapes and vegetables that grow on vines. The prime example is Peronospora farinosa featured in NCBI-Taxonomy and HYP3. This pathogen does not produce survival structures in the northern states of the United States, and overwinters as live mildew colonies in Gulf Coast states. It progresses northward with cucurbit production each spring. Yield loss associated with downy mildew is most likely related to soft rots that occur after plant canopies collapse and sunburn occurs on fruit. Cucurbit downy mildew only affects leaves of cucurbit plants.

<span class="mw-page-title-main">Captan</span> Chemical compound

Captan is a general use pesticide (GUP) that belongs to the phthalimide class of fungicides. It is a white solid, although commercial samples appear yellow or brownish.

<i>Phytophthora palmivora</i> Species of single-celled organism

Phytophthora palmivora is an oomycete that causes bud-rot of palms, fruit-rot or kole-roga of coconut and areca nut. These are among the most serious diseases caused by fungi and moulds in South India. It occurs almost every year in Malnad, Mysore, North & South Kanara, Malabar and other areas. Similar diseases of palms are also known to occur in Sri Lanka, Mauritius, and Sumatra. The causative organism was first identified as P. palmivora by Edwin John Butler in 1917.

Phytophthora citrophthora, also known as brown rot of citrus, is a soil borne oomycete that infects several economically important citrus crops. A diagnostic symptom of P. citrophthora is gummosis, wherein lesions around the base of the tree exude sap. Other common symptoms include dark longitudinal lesions forming at the soil line, a sour smell, and eventual cracking of the bark. Advanced symptoms include yellowing and necrosis of the tree canopy. Girdling action caused by the pathogen around the trunk can often cause the collapse of the tree. Resistant lemon varieties have been developed and their implementation has been effective at controlling the spread of the disease. Fruits that have been infected with P. citrophthora exhibit symptoms of brown rot characterized by a distinct odor. This disease is most active in the moderate temperatures of spring, fall, and winter months, opposite of most other Phytophthora species.

Pythium irregulare is a soil borne oomycete plant pathogen. Oomycetes, also known as "water molds", are fungal-like protists. They are fungal-like because of their similar life cycles, but differ in that the resting stage is diploid, they have coenocytic hyphae, a larger genome, cellulose in their cell walls instead of chitin, and contain zoospores and oospores.

<i>Peronospora sparsa</i> Species of single-celled organism

Peronospora sparsa is an oomycete plant pathogen that causes downy mildew in berry producing plants; especially in the genus's Rubus and Rosa. Downy mildew plant pathogens are often host specific and cause problems in cloudberries, blackberries, boysenberries, strawberries, and arctic bramble. Since they are host specific, Peronospora sparsa will not cause downy mildew in grapes because a different plant pathogen causes downy mildew in grapes; Plasmopara viticola. Although it depends on the cultivar, symptoms do not normally start until later stages of disease and can look different on different plants. The most common symptoms include red lesions in the veins of leaves, with dry and deformed berries.

Peronospora trifoliorum, commonly known as downy mildew of alfalfa, is an oomycete plant pathogen infecting alfalfa.

Phytophthora erythroseptica—also known as pink rot along with several other species of Phytophthora—is a plant pathogen. It infects potatoes causing their tubers to turn pink and damages leaves. It also infects tulips (Tulipa) damaging their leaves and shoots.

Phytophthora megakarya is an oomycete plant pathogen that causes black pod disease in cocoa trees in west and central Africa. This pathogen can cause detrimental loss of yield in the economically important cocoa industry, worth approximately $70 billion annually. It can damage any part of the tree, causing total yield losses which can easily reach 20-25%. A mixture of chemical and cultural controls, as well as choosing resistant plant varieties, are often necessary to control this pathogen.

<i>Septoria malagutii</i> Species of fungus

Septoria malagutii is a fungal plant pathogen infecting potatoes. The casual fungal pathogen is a deuteromycete and therefore has no true sexual stage. As a result, Septoria produces pycnidia, an asexual flask shaped fruiting body, on the leaves of potato and other tuber-bearing spp. causing small black to brown necrotic lesions ranging in size from 1-5mm. The necrotic lesions can fuse together forming large necrotic areas susceptible to leaf drop, early senescence, dieback, and dwarfing. Septoria malagutii has been found only in the Andean countries of Bolivia, Ecuador, Peru, and Venezuela at altitudes of near 3000 meters. Consequently, the fungi grows and disperses best under relatively low temperatures with high humidities, with optimal growth occurring at 20 °C (68 °F). The disease has caused devastation on potato yields in South America and in areas where this disease is common, potato yields have been seen to drop by 60%.

<span class="mw-page-title-main">Azoxystrobin</span> Chemical compound

Azoxystrobin is the ISO common name for an organic compound that is used as a fungicide. It is a broad spectrum systemic active ingredient 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.

<i>Peronospora hyoscyami</i> f.sp. <i>tabacina</i> Subspecies of single-celled organism

Peronospora hyoscyami f.sp. tabacina is a plant pathogen infecting tobacco that causes blue mold. It is an oomycete that is highly destructive toward seed plants. It is very prevalent in humid farming zones, like the southeastern and Eastern U.S., Canada, and countries bordering the Caribbean. The disease was first identified in 1921 in Florida and Georgia. Ten years later the same disease was found once again in the same region of the U.S. The disease began to spread into Virginia, Maryland, and North Carolina. A few years later, the disease reached Kentucky and Tennessee. In 1960, a blue mold epidemic spread in approximately eleven countries. There was approximately twenty five million dollars in losses which is nearly thirty percent of tobacco plants at the time. Each year, Peronospora hyoscyami is introduced as blue mold as windblown spores from outside the region by infected transplants.

Copper pesticides are copper compounds used as bactericides, algaecides, or fungicides. They can kill bacteria, oomycetes and algae, and prevent fungal spores from germinating. Common forms of fixed copper fungicides include copper sulfate, copper sulfate pentahydrate, copper hydroxide, copper oxychloride sulfate, cuprous oxide, and copper octanoate.

<i>Peronospora destructor</i> Species of single-celled organism

Peronospora destructor is a plant pathogen. It causes downy mildew on leaves of cultivated and wild Allium. Allium cepa is most often affected, while Allium schoenoprasum (chives) and Allium porrum (leek) are only occasionally affected.

<span class="mw-page-title-main">Lactofen</span> Chemical compound

Lactofen is a complex ester of acifluorfen and is a nitrophenyl ether selective herbicide and fungicide. It is used in postemergence applications to certain crops which are resistant to its action. The name "Lactofen" is approved by the American National Standards Institute and the Weed Science Society of America, and is also approved in China (乳氟禾草灵).

Tree injection—also known as trunk injection or stem injection,—is a method of targeting a precise application of pesticides, plant resistance activators, or fertilizers into the xylem vascular tissue of a tree with the purpose of protecting the tree from pests, or to inject nutrients to correct for nutrient deficiencies. This method largely relies on harnessing the tree's vascular system to translocate and distribute the active compounds into the wood, canopy and roots where protection or nutrition is needed.

<span class="mw-page-title-main">Oxathiapiprolin</span> Chemical compound

Oxathiapiprolin is a fungicide. In the United States, the Environmental Protection Agency has approved it for use against several fungal diseases including downy mildew and various Phytophthora species including late blight on crops including vegetables, ornamentals, and turf.

References

  1. 1 2 3 Valérie Toquin; Marie-Pascal Latorse; Roland Beffa (2012). Modern Crop Protection Compounds. John Wiley & Sons. pp. 831–838. ISBN   978-3-527-32965-6.
  2. 1 2 3 "Fluopicolide Toxicology" (PDF). Food and Agriculture Organization.
  3. U. Gisi; Ilan Chet; Maria Lodovica Gullino (18 September 2009). Recent Developments in Management of Plant Diseases. Springer Science & Business Media. p. 19. ISBN   978-1-4020-8804-9.
  4. "Bayer CropScience's Infinito receives best combined rating". Biotech Week. 2007-06-20.
  5. 1 2 3 Valérie Toquin; Francois Barja; Catherine Sirven; Roland Beffa (2007). "Fluopicolide, a new Anti-oomycetes Fungicide with a New Mode of Action inducing Perturbation of a Spectrin-like Protein". Modern Crop Protection Compounds. pp. 675–682. doi:10.1002/9783527619580.ch19. ISBN   9783527619580.