- Source: Propanil
- Propanil
- Dawson Chemical Co. v. Rohm & Haas Co.
- 3,4-Dichloroaniline
- Gemmobacter nanjingensis
- DCPA
- Herbicide
- Emilia sonchifolia
- HRAC classification
- Oryzisolibacter
- List of herbicides
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Propanil is a widely used contact herbicide. With an estimated use of about 8 million pounds in 2001, it is one of the more widely used herbicides in the United States. Propanil is said to be in use in approximately 400,000 acres of rice production each year.
Mode of action
The principal mode of propanil's herbicidal action against weeds is inhibition of their photosynthesis and CO2 fixation. Plants photosynthesize in two stages. In stage I photosynthetic reactions capture sunlight energy and yield molecules with high energy content. In stage II these molecules react to capture CO2, yielding carbohydrate precursors. In the stage I reaction a chlorophyll molecule absorbs one photon (light) and loses one electron, starting an electron transport chain reaction leading to the stage II reactions. Propanil inhibits the electron transport chain reaction and its conversion of CO2 to carbohydrate precursors. That inhibits further development of the weed.
Rice is relatively immune to propanil but most weeds are susceptible to it. The reason for the selectivity is that rice contains a high level of the enzyme aryl acylamidase (AAA), which rapidly metabolizes propanil to relatively nontoxic 3,4-dichloroaniline. Susceptible weeds lack the gene(s) coding for the AAA enzyme and thus succumb to propanil. However, intensive use of propanil and natural selection have caused some weeds to become resistant to propanil.
Synthesis
Propanil is made industrially by nitration of 1,2-dichlorobenzene (1) to give 1,2-dichloro-4-nitrobenzene (2), followed by hydrogenation of the nitro group with Raney nickel to give 3,4-dichloroaniline (3). Acylation of the amine with propanoyl chloride yields propanil (4). The resulting product is white or brown crystals.
Patent litigation
Propanil was the subject of several patent infringement suits. In one, Monsanto Co. v. Rohm and Haas Co., the United States Court of Appeals for the Third Circuit held that Monsanto committed fraud on the Patent Office in procuring its patent on propanil.
Monsanto obtained the patent by providing data to the Patent Office showing that propanil "had "unusual and valuable herbicidal activity" and that its activity was "surprising" because "related compounds possess little or no herbicidal efficiency." Monsanto had conducted a number of tests and submitted test data to the Patent Office that indicated that propanil was superior to other similar chemicals, including one chemical that differed from propanil only in eliminating the CH2 group to the left of the CH3 group at the far right of the diagram shown at above right. (The two chemicals are so-called adjacent homologues.)
But Monsanto had withheld data on those tests that showed that other similar compounds also had herbicidal activity similar to that of propanil. The court said that this amounted to a misrepresentation and Monsanto was not entitled to a patent, so that the patent was invalid or unenforceable. In an earlier case, however, a judge had accepted Monsanto's argument that Monsanto "did nothing more than put their best foot forward" with the Patent Office.
References
External links
Propanil in the Pesticide Properties DataBase (PPDB)
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Artikel Terkait "propanil"
Propanil - Wikipedia
Propanil is a widely used contact herbicide. With an estimated use of about 8 million pounds in 2001, it is one of the more widely used herbicides in the United States. [2] Propanil is said to be in use in approximately 400,000 acres of rice production each year. [3]
Propanil | C9H9Cl2NO | CID 4933 - PubChem
Propanil | C9H9Cl2NO | CID 4933 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more.
Propanil - Chemical Details | Chemical Search | Pesticides - US …
30 Apr 1998 · Pesticide substance information for Propanil including science reviews, decisions and fact sheets.
US EPA - Pesticides - Fact Sheet for Propanil
Propanil is a selective post-emergent use herbicide registered to control broadleaf and grass weeds on rice. It is also registered (but not currently marketed) for turf use at commercial sod farms. The small grain use was voluntarily cancelled. There are no residential uses of propanil.
Chemical fact sheets: Propanil - World Health Organization (WHO)
18 Mei 2022 · Chapter 12 of the Guidelines for drinking-water Quality (GDWQ) includes fact sheets on chemical contaminants, based on comprehensive review documents published by WHO.
Propanil - Active Ingredient Page — Chemical Warehouse
Propanil, chemically known as 3',4'-Dichloropropionanilide, is a post-emergent herbicide primarily used in rice cultivation. It is known for its effectiveness in controlling a wide range of grass and broadleaf weeds. Available in various formulations, Propanil is typically applied as a foliar spray.
Propanil - an overview | ScienceDirect Topics
Propanil is a postemergence herbicide used primarily on rice and wheat to control grass weeds. It can be formulated as an emulsifiable concentrate, liquid, or dry flowable substance.
Clinical outcomes and kinetics of propanil following acute self ...
Propanil (3,4-dichloropropionanilide) is a selective acylanilide herbicide used widely in rice cultivation in many parts of the world. It may be the most extensively used herbicide for rice production worldwide [1] and is ranked within the top 20 pesticides used for agriculture in the United States. [2] .
Propanil certified reference material, TraceCERT®, Manufactured …
Propanil is a post-emergence herbicide used for broad-leaved and annual grass weed control in rice and other crops such as wheat, potatoes. It is moderately soluble in water and has a low volatility. It is not approved according to Reg. (EC) No 1107/2009 for use as a plant protection product in the European Union.
12. CHEMICAL FACT SHEETS - World Health Organization …
Propanil (CAS No. 709-98-8) is a contact post-emergence herbicide used to con-trol broad-leaved and grassy weeds, mainly in rice. It is a mobile compound with afinity for the water compartment. Propanil is not, however, persistent, being easily t ransformed under natural conditions to …