Phenylpyrazole amide herbicides

Moon, Malcolm W.; Bell, Larry T.; Cutting, Todd L.; Keyser, Henry R.; Tiller, Russell H.; Vostral, Henry J.

doi:10.1021/jf60213a016

Cited by 6 publications

(2 citation statements)

References 9 publications

(9 reference statements)

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“…Phenylpyrazoles are an important class of heterocycles that are present in many natural products and pharmaceutical intermediates . Moreover, phenylpyrazole derivatives containing fluorine groups have been found to exhibit a broad range of biological activities .…”

Section: Introductionmentioning

confidence: 99%

The Synthesis of Fipronil Derivatives via Pd‐Catalyzed Direct Alkynylation of Phenylpyrazole with Terminal Alkynes in Green Solvents

Chen

Zhang

2016

Journal of Heterocyclic Chem

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The palladium‐catalyzed direct alkynylation of phenylpyrazole (5‐amino‐1‐[2, 6‐dichloro‐4‐trifluoromethylphenyl]‐lH‐pyrazole‐3‐carbonitrile) with terminal alkynes is being reported. The protocol utilizes EtOH/H2O as the solvents and does not require the preactivation of phenylpyrazole with halide to form its halide substrate, which exemplifies the ideal condition of green chemistry. Various terminal alkynes such as arylacetylenes and aliphatic alkynes are used in the reaction to afford a series of fipronil derivatives of 4‐alkynyl‐1‐phenylpyrazoles with potential bioactivity in good yields. All the compounds were characterized by 1H NMR, 13C NMR, and HRMS spectroscopic techniques.

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Section: Introductionmentioning

confidence: 99%

The Synthesis of Fipronil Derivatives via Pd‐Catalyzed Direct Alkynylation of Phenylpyrazole with Terminal Alkynes in Green Solvents

Chen

Zhang

2016

Journal of Heterocyclic Chem

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“…In short-term experiments, peroxidative properties of this herbicide were negligible when using concentrations of 1 µ . In addition, phytotoxic activities of substituted hydroxypyrazoles (Moon et al, 1977) of a tetrahydrophthalimide derivative (Wakabayashi et al, 1979) are-at least in part-also due to inhibition of chlorophyll formation.…”

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confidence: 99%

Herbicidal mode of action on chlorophyll formation

Sandmann¹,

Reck²,

Boeger³

1984

J. Agric. Food Chem.

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Table II. Concentration of Ethalfluralin and Trifluralin Measured with a GC-MS-NCI and a GC-ECD0 j"vs concentration, rate, after ng/g of oven-dry soil kg/ha treatment GC-MS-NCI GC-ECD Ethalfluralin 1.0 199 46 50 1.5 199 124 129 1.0 555 12 12 1.5 555 16 23 standard error of mean for methods of analysis = 2.6 Trifluralin 1.0 199 122 126 1.5 199 206 192 1.0 555 57 65 1.5 555 89 85 standard error of mean for methods of analysis =4.80 Differences in concentration of trifluralin and ethalfluralin due to rates and sampling dates were significant and differences between GC-MS-NCI and GC-ECD were not significant (P = 0.05) by analysis of variance.(Lethbridge Research Station, unpublished data). Thus, the GC-MS-NCI can be used to confirm levels of ethalfluralin and trifluralin residues that are toxic to plants.The ability to analyze trifluralin and ethalfluralin with the GC-MS-NCI indicates that this system has potential for rapidly confirming structures and concentrations of several pesticides with a positive electron affinity in soil extracts. ACKNOWLEDGMENTWe thank Drs.

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Sequential Cleavage of Lignin Systems by Nitrogen Monoxide and Hydrazine

Hofmann¹,

Hofmann²,

Prusko³

et al. 2020

Adv Synth Catal

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The cleavage of representative lignin systems has been achieved in a metal‐free two‐step sequence first employing nitrogen monoxide for oxidation followed by hydrazine for reductive C−O bond scission. In combining nitrogen monoxide and lignin, the newly developed valorization strategy shows the particular feature of starting from two waste materials, and it further exploits the attractive conditions of a Wolff‐Kishner reduction for C−O bond cleavage for the first time.

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Phenylpyrazole amide herbicides

Cited by 6 publications

References 9 publications

The Synthesis of Fipronil Derivatives via Pd‐Catalyzed Direct Alkynylation of Phenylpyrazole with Terminal Alkynes in Green Solvents

The Synthesis of Fipronil Derivatives via Pd‐Catalyzed Direct Alkynylation of Phenylpyrazole with Terminal Alkynes in Green Solvents

Herbicidal mode of action on chlorophyll formation

Sequential Cleavage of Lignin Systems by Nitrogen Monoxide and Hydrazine

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