219714-96-2

Basic information

• Product Name: Penoxsulam
• Synonyms: PENOXSULAM;de-638;2-(2,2-difluoroethoxy)-N-(5,8-diMethoxy[1,2,4]triazolo[1,5-c]pyriMidin-2-yl)-6-(trifluoroMethyl)benzenesulfonaMide;3-(2,2-Difluoroethoxy)-N-(5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)-α,α,α-trifluorotoluene-2-sulfonamide;Penoxsulam Solution, 1000ppm
• CAS NO: 219714-96-2
• Molecular Formula: C16H14F5N5O5S
• Molecular Weight: 483.37
• EINECS: 1806241-263-5
• Product Categories: herbicide
• Mol File: 219714-96-2.mol

Chemical Properties

• Melting Point: 223-224°
• Appearance: /
• Density: 1.65g/cm³
• Refractive Index: 1.588
• Storage Temp.: 0-6°C
• PKA: 5.1(at 25℃)
• BRN: 10301178
• CAS DataBase Reference: Penoxsulam(CAS DataBase Reference)
• NIST Chemistry Reference: Penoxsulam(219714-96-2)
• EPA Substance Registry System: Penoxsulam(219714-96-2)

Safety Data

• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 219714-96-2(Hazardous Substances Data)

Usage

Uses

Used in Rice Agriculture:
Penoxsulam is used as a herbicide for controlling aquatic weeds and barnyard grass, which has resistance to other herbicides like quinclorac, propanil, and sulfonylurea. It is applied in paddy fields and plays a vital role in weed control due to the increasing resistance of aquatic weeds.
Used in Various Crops:
Penoxsulam is used as a post-emergency foliar spray or a granular formulation for the control of broadleaf, sedge, and grass weeds in transplanted, dry-seeded, and water-seeded rice. It is also effective against broadleaf weeds in corn, sorghum, wheat, barley, and other cereal crops, as well as in lawns, golf courses, parks, cemeteries, athletic fields, sod farms, tree and vine crops, range and pasture, roadsides, and other crop and non-crop uses.
Used in Environmental Management:
Penoxsulam is a systemic herbicide that moves throughout plant tissue and prevents plants from producing the necessary enzyme, acetolactate synthase (ALS), which is not found in animals. It may be used to treat invasive species such as the Eurasian watermilfoil (Myriophyllum spicatum) and hydrilla (Hydrilla verticillata). However, it can also affect desirable native species like sago pondweed (Stuckenia pectinata), Illinois pondweed (Potamogeton illinoensis), pickerelweed (Pontederia cordata), duckweeds (Lemna spp.), and arrowhead (Sagittaria spp.).
Used in Groundwater Contamination Prevention:
Due to its high mobility in aqueous and terrestrial environments, Penoxsulam tends to be a contaminant to groundwater. It is registered for use in Germany, France, Portugal, and the USA, where efforts are made to minimize its impact on groundwater quality.

Mechanism of action

In the mammalian metabolism studies, penoxsulam was rapidly and almost completely absorbed upon oral administration. There was no evidence of bioaccumulation. Excretion was rapid, but dose and sex dependent as excretion was primarily observed via faeces in males and primarily excreted in urine in females. Penoxsulam was bio-transformed to a large number of metabolites; however the majority of the radioactivity was eliminated as unchanged parent compound.

Degradation

Penoxsulam can be quickly absorbed by the soil. Leachability is weak in most paddy soils. Its adsorption capacity in clay soil and soil with high organic matter is higher than that in light soil and soil with low organic matter content. In soil with pH>8.0, it has the risk of aggravating phytotoxicity. The agent is easy to migrate in the soil and does not stay long-term. Due to the low saturated vapor pressure of the agent, it is not easy to evaporate from the water; in the irrigated rice field, the lookchem half-life of the agent is 2-13d; photolysis and microbial degradation are the main disappearance ways of penoxsulam. It is resistant to hydrolysis in water, but it can quickly disappear after photolysis in shallow water. The photolysis of the aqueous solution is divided into three ways: sulfophthalamide bridge cleavage, the gradual degradation of trimethoprim and its substituents, and sulfophthaleyl photooxidation . This photolysis product can remain for a long time. In paddy soil, anaerobic microbial degradation is an important process for the disappearance of pesticides, and its disappearance speed is as fast as photolysis.

References

[1] Patent: US 20140274711 A1 “Synergistic weed control from applications of penoxsulam and pethoxamid” [2] http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/512.htm [3] alyani Paranjape, Vasant Gowariker, V N Krishnamurthy, Sugha Gowariker, The Pesticide Encyclopedia (2014)

InChI:InChI=1/C16H14F5N5O5S/c1-29-10-6-22-15(30-2)26-13(10)23-14(24-26)25-32(27,28)12-8(16(19,20)21)4-3-5-9(12)31-7-11(17)18/h3-6,11H,7H2,1-2H3,(H,24,25)

Upstream product

• 219715-62-5 2-amino-5,8-dimethoxy[1,2,4]triazolo-[1,5-c]pyrimidine 
• 98-17-9 3-Trifluoromethylphenol 
• 896732-43-7 2-(3-(trifluoromethyl)phenoxy)tetrahydro-2H-pyran 
• 1431291-88-1 2-bromo-6-trifluoromethybenzenesulfonyl chloride 
• 1431291-89-2 2-bromo-6-trifluoromethybenzenesulfonic acid 
• 1431291-90-5 2-bromo-4-amino-6-trifluoromethybenzenesulfonic acid 
• 1451065-56-7 2-bromo-4-acetamido-6-trifluoromethybenzenesulfonic acid 
• 1431291-92-7 2-bromo-4-acetamido-6-trifluoromethylaniline 
• 359-13-7 difluoroethanol 
• 1431291-87-0 2-bromo-6-trifluoromethyl-N-(5,8-dimethoxy-1,2,4-triazolo[1,5-c]pyrimidine-2-yl)benzenesulfonamide 
• 108761-81-5 2-bromo-4-amino-6-trifluoromethylaniline 
• 1451065-57-8 C₇H₃BrF₃O₃S^(1-)*K⁽¹⁺⁾ 
• 400-66-8 2-bromo-4-nitro-6-trifluoromethylaniline 
• 453560-57-1 N-(3-bromo-5-trifluoromethyl-phenyl)-acetamide 

Relevant articles and documents

HERBICIDAL COMPOSITIONS

The present invention provides compositions comprising herbicidally active compounds (A) and (B), where (A) represents one or more compounds of the general formula (I) or agrochemically compatible salts thereof [component (A)], and (B) represents one or more herbicides [component (B)]. The application further relates to a method and to the use of the herbicidal composition according to the invention for controlling harmful plants or for regulating growth.

Improved [...] synthetic method

The invention discloses an improved synthetic method of penoxsulam. The improved synthetic method comprises the following steps: taking a strong-alkalinity substance, difluoroethanol and 2-fluoro-6-trifluoromethyl-N-(5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyr

Preparation method of penoxsulam

The invention provides a preparation method of penoxsulam. The preparation method comprises the following steps: (1) carrying out substitution reaction on m-trifluoromethyl phenol and 2-chloro-1,1-difluoroethane by taking the m-trifluoromethyl phenol as a raw material, thus obtaining m-difluoroethoxy trifluorotoluene (reaction I); (2) enabling the generated m-difluoroethoxy trifluorotoluene to react with sulfuryl fluoride, thus obtaining 2-(2',2'-difluoroethoxy)-6-trifluoromethyl phenyl sulfuryl fluoride (reaction II); (3) enabling the generated 2-(2',2'-difluoroethoxy)-6-trifluoromethyl phenyl sulfuryl fluoride to react with 5,8-dimethoxy-[1,2,4]triazole[1,5-c]pyrimidine-2-amine in a (water-soluble) organic solvent under the action of base, thus obtaining the penoxsulam (reaction III). According to the preparation method provided by the invention, the raw material is cheap and easy to obtain, the technology is safe, the operation is simple, and industrial production is convenient.

2 - phenoxy four hydrogens fu ([...]) five fluorine sulphur grass amine[...] derivatives and their application in the synthesis of

The invention discloses 2-phenoxyl tetrahydrofuran (tetrahydropyrane) derivatives and the application thereof in synthesis of penoxsulam, and belongs to the field of pesticide synthesis. A new intermediate of a penoxsulam pesticide is synthesized by the derivatives of the design of the invention. A high-toxicity raw material is not required to be used in the preparation of the intermediate; a product is convenient to purify and high in yield; a synthesizing process is environment-friendly; the synthesis cost is low. The penoxsulam pesticide can be prepared conveniently by utilizing the intermediate; the intermediate has a good application prospect. The series of derivatives are easy and convenient to synthesize; compared with the reported penoxsulam intermediate, a low-boiling-point raw material with high toxicity, namely, chloromethyl methyl ether, is not required to be used in the synthesizing process; the safety of the synthesizing process is improved; the derivatives are favorable to industrialized production and application.

An efficient synthesis of 2-(2,2-difluoroethoxy)-6-trifluoromethyl-n-(5,8- dimethoxy-1,2,4-triazolo[1,5-c]pyrimidine-2-yl) benzenesulfonamide: Penoxsulam

An efficient nine-step synthesis of 2-(2,2-difluoroethoxy)-6- trifluoromethyl-N-(5,8-dimethoxy-1,2,4-triazolo[1,5-c] - pyrimidine-2-yl) benzenesulfonamide has been developed. The starting material 4-nitro-2-(trifluoromethyl)aniline starting material was converted via 2-bromo-4-amino-6-trifluoromethylaniline and 2-bromo-4-acetamido-6- trifluoromethylbenzenesulfonic acid to 2-bromo-6-trilfuoromethylbenzenesulfonic acid. This was then combined with 2-amino-5,8-dimethoxy-1,2,4-triazolo[1.5-c] pyrimidine to give the target molecule. Compared with the reported method, this approach has advantages in its shorter reaction time, milder reaction conditions and easier purifiction. Moreover, the overall yield has been improved to 22.9% which is twice of that of the reported method.

Penoxsulam-Structure-activity relationships of triazolopyrimidine sulfonamides

The discovery of the sulfonamide herbicides, which inhibit the enzyme acetolactate synthase (ALS), has resulted in many investigations to exploit their herbicidal activity. One area which proved particularly productive was the N-aryltriazolo[1,5-c]pyrimidine sulfonamides, providing three commercial herbicides, cloransulam-methyl, diclosulam and florasulam. Additional structure-activity investigations by reversing the sulfonamide linkage resulted in the discovery of triazolopyrimidine sulfonamides with cereal crop selectivity and high levels of grass and broadleaf weed control. Research efforts to exploit these high levels of weed activity ultimately led to the discovery of penoxsulam, a new herbicide developed for grass, sedge and broadleaf weed control in rice. Synthetic efforts and structure-activity relationships leading to the discovery of penoxsulam will be discussed.

Process for the preparation of N-([1,2,4]triazolopyrimidin-2-yl)aryl sulfonamides

The N-arylsulfilimine-catalyzed coupling of aromatic sulfonyl chlorides with N-([1,2,4]triazolopyrimidin-2-yl)amines to form N-([1,2,4]triazolo-pyrimidin-2-yl)aryl sulfonamides is improved by the selection of 3-picoline or 3,5-lutidine as the base.

Process for the preparation of 2-alkoxy-6-trifluoromethyl-N-([1,2,4]triazolo[1,5-c]pyrimidin-2-yl)benzenesulfonamides

2-Alkoxy-6-trifluoromethyl-N-([1,2,4]triazolo[1,5-c]pyrimidin-2-yl)benzenesulfonamides are prepared by introducing the 2-alkoxy substituent of the benzenesulfonamide ring in the last step by contacting the corresponding 2-fluoro substituted material with the appropriate alkoxide.