19666-30-9

Usage

Air & Water Reactions

Dust may form an explosive mixture in air.

Reactivity Profile

Oxadiazon is a diazo compound. Azo, diazo, azido compounds can detonate. This applies in particular to organic azides that have been sensitized by the addition of metal salts or strong acids. Toxic gases are formed by mixing materials of this class with acids, aldehydes, amides, carbamates, cyanides, inorganic fluorides, halogenated organics, isocyanates, ketones, metals, nitrides, peroxides, phenols, epoxides, acyl halides, and strong oxidizing or reducing agents. Flammable gases are formed by mixing materials in this group with alkali metals. Explosive combination can occur with strong oxidizing agents, metal salts, peroxides, and sulfides.

Trade name

CARPETMAKER?; CHIP SHOT?[C]; GOLD KIST?; PAR EX?; PRO GROW?; REGAL O-O?; REGALSTAR?; RONSTAR?; RP-17623?; TURFIC?; VERTAGREEN?; WILBRO

Safety Profile

Moderately toxic by ingestion, inhalation, and skin contact. When heated to decomposition it emits toxic vapors of NOx and Clí.

Potential Exposure

An oxadiazolinone/oxidiazole preemergence and early postemergence herbicide used to control annual grasses, sedges, and broadleaf weeds. Originally registered for use on turf and ornamentals; has wide use on golf courses.

Environmental Fate

Soil. The reported half-life in soil is approximately 3–6 months (Hartley and Kidd, 1987). Oxadiazon degraded slowly in both moist and flooded soils. After 25 weeks, only 0.1–3.5% degraded to carbon dioxide and 0.5–1.1% as volatile products. Metabolites identified included oxadiazonphenol, oxadiazon acid and methoxyoxadiazon (Ambrosi et al., 1977).Plant. Reported half-lives of oxadiazon in rice and orchard fruit are 1–2 and 3–6 months, respectively (Hartley and Kidd, 1987).

Shipping

UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.

Incompatibilities

Dust may form explosive mixture in air. Diazo compounds can detonate. This applies in particular to organic azides that have been sensitized by the addition of metal salts or strong acids. Toxic gases are formed by mixing materials of this class with acids, aldehydes, amides, carbamates, cyanides, inorganic fluorides, halogenated organics, isocyanates, ketones, metals, nitrides, peroxides, phenols, epoxides, acyl halides, and strong oxidizing or reducing agents. Flammable gases are formed by mixing materials in this group with alkali metals. Explosive combination can occur with strong oxidizing agents, metal salts, peroxides, and sulfides. This chemical is sensitive to prolonged exposure to heat. This chemical is incompatible with strong oxidizing agents.

Waste Disposal

It is the responsibility of chemical waste generators to determine the toxicity and physical properties and of a discarded chemical and to properly identify its classification and certification as a hazardous waste, and to determine the disposal method. United States Environmental Protection Agency guidelines for the classification determination are listed in 40 CFR Parts 261.3. Additionally, waste generators must consult and follow all regional, national, state, and local hazardous waste laws to ensure complete and accurate classification and disposal methods. Follow recommendations for the disposal of pesticides and pesticide containers. Containers must be disposed of properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office. Do not discharge into drains or sewers. Dispose of waste material as hazardous waste using a licensed disposal contractor to an approved landfill. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. If allowed, incineration with effluent gas scrubbing is recommended. Containers must be disposed of properly by following package label directions or by contacting your local or federal environment

InChI:InChI=1/C15H18Cl2N2O3/c1-8(2)21-12-7-11(9(16)6-10(12)17)19-14(20)22-13(18-19)15(3,4)5/h6-8H,1-5H3

Upstream product

• 124-38-9 carbon dioxide 
• 51166-88-2 pivaloyl chloride-2,4-dichloro-5-isopropoxy-N-phenylhydrazone 
• 630-19-3 pivalaldehyde 
• 40178-22-1 2,4-dichloro-5-(1-methylethoxy)phenylhydrazine 
• 56578-26-8 1-(2,4-dichloro-5-isopropoxyphenyl)-1-(methoxycarbonyl)-1,2-trimethylacetyl hydrazine 

Downstream Products

• 6851-40-7 2,4-dichloro-1-isopropoxybenzene 
• 51167-18-1 1-trimethylacetyl-2-(2,4-dichloro-5-isopropoxyphenyl) hydrazine 
• 56578-26-8 1-(2,4-dichloro-5-isopropoxyphenyl)-1-(methoxycarbonyl)-1,2-trimethylacetyl hydrazine 

Related news

Biodegradation of Oxadiazon (cas 19666-30-9) by a soil isolated Pseudomonas fluorescens strain CG5: Implementation in an herbicide removal reactor and modelling09/09/2019

An oxadiazon-degrading bacterial, Pseudomonas strain CG5, was isolated from an agricultural contaminated soil. This strain CG5 was able to grow on 10 mg of oxadiazon per l, yielding 5.18±0.2 mg of protein biomass mol−1. GC-MS analyses of the metabolites from oxadiazon catabolism revealed its de...detailed

Determination of Oxadiazon (cas 19666-30-9) residues by headspace solid-phase microextraction and gas chromatography–mass spectrometry09/08/2019

A method for the determination of trace amounts of the herbicide oxadiazon was developed using headspace solid-phase microextraction (HS-SPME), gas chromatography–mass spectrometry (GC–MS) and selected ion monitoring. It was applied to determine oxadiazon in ground water, agricultural soil, mu...detailed

Effect of the herbicides Oxadiazon (cas 19666-30-9) and oxyfluorfen on phosphates solubilizing microorganisms and their persistence in rice fields09/07/2019

A field experiment has been conducted with two herbicides viz. oxadiazon [5-terbutyl-3-(2,4-dichloro-5-isopropoxyphenyl)-1,3,4-oxadiazol-2-one] and oxyfluorfen [2-chloro-1-(3-ethoxy-4-nitrophenyl)-4-(trifluoromethyl) benzene] at rates of 0.4 and 0.12 kg a.i. ha−1, respectively, to investigate th...detailed

Degradation of Oxadiazon (cas 19666-30-9) in a bioreactor integrated in the water closed circuit of a plant nursery09/06/2019

Hardy ornamental nursery stock (HONS) use fertigation as a rational supply of nutrients all along the growth cycle of plants. Nevertheless, that frequency of irrigation increases the risks of nutrient and herbicide leaching and subsequent contamination of the waste water. Therefore, systems of w...detailed

Oxadiazon (cas 19666-30-9) affects the expression and activity of aldehyde dehydrogenase and acylphosphatase in human striatal precursor cells: A possible role in neurotoxicity08/31/2019

Exposure to herbicides can induce long-term chronic adverse effects such as respiratory diseases, malignancies and neurodegenerative diseases. Oxadiazon, a pre-emergence or early post-emergence herbicide, despite its low acute toxicity, may induce liver cancer and may exert adverse effects on re...detailed

Relevant academic research and scientific papers

One-pot synthesis of 1,3,4-oxadiazol-2(3H)-ones with CO2 as a C1 synthon promoted by hypoiodite

A convenient and efficient route has been developed to synthesize 1,3,4-oxadiazol-2(3H)-ones from CO2, hydrazines and aryl or aliphatic aldehydes. Promoted by hypoiodite (IO-) generated in situ from KI and oxidant TBHP, the one-pot synthesis could proceed smoothly to afford the desired products in moderate to high yields. Mechanism studies revealed that nitrile imine was an important intermediate in this transformation. Notably, a commercial herbicide Oxadiazon could be successfully synthesized by this route.

1,3-Dipolar Cycloaddition of Nitrile Imine with Carbon Dioxide: Access to 1,3,4-Oxadiazole-2(3H)-ones

Efficient synthesis of 1,3,4-oxadiazole-2(3H)-one was achieved by CsF/18-crown-6 mediated 1,3-dipolar cycloaddition of nitrile imine and 2.0 MPa of CO2. CsF/18-crown-6 played a key role in enhancing the reactivity of CO2 as a 1,3-dipolarophile. The practical utility of this transition-metal-free approach to 1,3,4-oxadiazole-2(3H)-one is highlighted by the convenient synthesis of a commercial herbicide Oxadiazon and a MAO B inhibitor.

Method for synthesizing 1,3,4-oxadiazole-2-one compounds of oxadiazon and the like by carbon dioxide

The invention discloses a method for synthesizing 1,3,4-oxadiazole-2-one compounds of oxadiazon and the like by carbon dioxide. The method comprises: adding an acyl halide hydrazone raw material and a solvent into a high-pressure autoclave; using alkali and an additive as accelerants, introducing carbon dioxide, and performing a stirring reaction for 6 to 24 hours at a temperature of 0 to 70 DEG C; after finishing the reaction, cooling to the room temperature; slowly releasing the unreacted carbon dioxide; after adding water to dilute reaction liquid, carrying out extraction by ethyl acetate; concentrating to obtain a crude product; purifying by column chromatography to obtain the 1,3,4-oxadiazole-2-one compounds. The method disclosed by the invention uses the carbon dioxide for replacing conventional phosgene and carbon monoxide, is safe and simple to operate, low in toxicity, friendly to the environment, simple and easy for obtaining reaction raw materials and reagents, wide in universality of a type of a reaction substrate, simple in post-processing process, high in target product yield and beneficial to industrial production, and is widely applied in synthesis of pesticides, medicines and natural products.

A process for synthesizing oxadiazon

The invention discloses a synthesis technology of oxadiazon. The synthesis technology comprises following steps: (A). carrying out a reaction between 2,4-dichloro-5-isopropoxylbenzhydrazide and methyl chloroformate in an organic solvent to obtain hydrazide methyl ester; (B). enabling the hydrazide methyl ester to be subjected to a cyclization reaction under the effect of a catalyst to obtain the oxadiazon. During the synthesis technology of the oxadiazon, the oxadiazon is synthesized with 2,4-dichloro-5-isopropoxylbenzhydrazide and methyl chloroformate being raw materials, wherein the methyl chloroformate is employed, instead of phosgene or triphosgene, as a carbonylation ring-closing reagent, so that safety potential risk during a conventional phosgene technology is avoided, which enables the synthesis technology of the oxadiazon to be high in safety. In addition, yield of the oxadiazon is high in the invention. An experimental result proves that the yield of the oxadiazon is higher than 97%.

HERBICIDAL COMPOSITIONS AND METHOD OF USING THE SAME

Herbicidal compositions containing as the active ingredients one or more compounds selected from among light-inducing herbicidal compounds and one or more compounds selected from among organoposphorus herbicidal compounds, characterized by containing ethylenediamine alkoxylates and alcohol alkoxylates as surfactants. These herbicidal compositions have an excellent rapid action and exert a remarkable herbicidal effect in a small dose.

Synergistic herbicidal mixtures

PCT No. PCT/EP96/04935 Sec. 371 Date May 1, 1998 Sec. 102(e) Date May 1, 1998 PCT Filed Nov. 12, 1996 PCT Pub. No. WO97/17852 PCT Pub. Date May 22, 1997A synergistically active herbicidal composition which comprises, as active components, a mixture of 1-(3-chloro-4,5,6,7-tetrahydropyrazolo-[1,5-a]-pyridin-2-yl)-5-(methylpropargylamino)-4-pyrazolylcarbonitrile [Component (A)] and a herbicide selected from the group consisting of bentazone, molinate, daimuron, thiobencarb, butachlor, pretilachlor, dimepiperate, fenoxaprop-ethyl, clomeprop, cinmethylin, bromobutide, quinclorac, mefenacet, pyrazosulfuron-ethyl, esprocarb, cinosulfuron, thenylchlor, cumyluron, MK 243, naproanilide, anilofos, benfuresate, bifenox, CH-900, MCPA, nitrofen, oxadiazon, pendimethalin, simetryn, sulcotrione (ICIA0051), trifluralin, piperophos, pyributicarb, ethoxysulfuron, bensulfuronmethyl, pyrazolate, pyrazoxyfen, benzofenap, cyclosulfamuron, cyhalofop-butyl, NBA-061, azimsulfuron, propanil or imazosulfuron [Component (B)] and which are suitable for controlling undesirable plants in rice cultivation.

Herbicidal sulfonamides

This invention relates to benzylsulfonylureas which are active pre- and post-emergence herbicides.

5,6-Dihydro-1,2,4,6-thiatriazin-5-one-1,1-dioxides

5,6-Dihydro-1,2,4,6-thiatriazin-5-one-1,1-dioxides of the formula STR1 where R1 is hydrogen, a metal atom or an unsubstituted or substituted ammonium radical, R2 is a saturated or unsaturated straight-chain aliphatic radical of up to 10 carbon atoms, a cycloaliphatic radical or 3 to 7 carbon atoms, a branched saturated or unsaturated aliphatic radical of 3 to 10 carbon atoms, a halogen-, alkoxy- or alkylmercapto-substituted aliphatic radical of 2 to 10 carbon atoms tetrahydrofuryl substituted methyl, a cycloalkoxy-substituted aliphatic radical of 4 to 10 carbon atoms, unsubstituted or halogen-substituted benzyl or phenyl, halophenyl, or alkylphenyl of a total of up to 10 carbon atoms, R3 is hydrogen, a straight-chain aliphatic radical of up to 10 carbon atoms, a cycloaliphatic radical of 3 to 7 carbon atoms, a branched aliphatic radical of 3 to 10 carbon atoms, haloalkyl, or alkoxyalkyl of 2 to 10 carbon atoms and X is oxygen and may also be sulfur if R2 is unsubstituted or halogen-substituted benzyl, processes for their preparation, and herbicides containing the above compounds.

Substituted phenoxyphenyl pyridazones, their preparation, and their use as herbicides

Substituted pyridazones of the general formula STR1 where R2 is halogen or alkoxy, R1 is amino, alkylamino, dialkylamino, alkoxyamino, alkylalkoxyamino, halogen, alkoxy, trimethyleneimino or acylated amino, X is unsubstituted or substituted phenoxy of the formula STR2 where R3, R4 and R5 are each, independently of one another, hydrogen, halogen, nitro, cyano, carboxyl, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylmercapto, haloalkylmercapto, alkylsulfinyl or alkylsulfonyl and Y is hydrogen, cyano, haloalkyl, halogen or nitro, and herbicides which contain these compounds.