Synthesis and activity optimization of herbicidal substituted 4-aryl-1,2,4-triazole-5(1H)-thiones

Simmons, Kirk A.; Dixson, John A.; Halling, Blaik P.; Plummer, Ernest L.; Plummer, Marjorie J.; Tymonko, John M.; Schmidt, Robert J.; Wyle, Mike J.; Webster, Charles A.

doi:10.1021/jf00014a027

Cited by 21 publications

(11 citation statements)

References 11 publications

(16 reference statements)

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“…Cyfluthrin, which is marketed under the trade name Baythroid, [21] is the remarkable result of a programme directed at the synthesis of all seven possible compounds with fluorinated alcohol modifications. [22] In comparison to cypermethrin (13), cyfluthrin realized a more than threefold reduction in use rate for the control of cotton pests. [23] As a result of its long-lasting residual action and ingestion effect, cyfluthrin (14) is also recommended as a houshold insecticide for the control of houseflies, mosquitoes, or cockroaches.…”

Section: Insecticides Containing Fluorine Pyrethroidesmentioning

confidence: 99%

“…The pyrethroids vary in their susceptibility to light. Aqueous solutions of cyfluthrin (14) are fairly susceptible; cypermethrin (13) and cyhalothrin (15) not quite as susceptible. The relative insecticidal activity of established pyrethroids against houseflies compared with their relative mammalian toxicity to rats is depicted in Figure 4.…”

Section: Insecticides Containing Fluorine Pyrethroidesmentioning

confidence: 99%

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The Unique Role of Fluorine in the Design of Active Ingredients for Modern Crop Protection

2004

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The task of inventing and developing active ingredients with useful biological activities requires a search for novel chemical substructures. This process may trigger the discovery of whole classes of chemicals of potential commercial interest. Similar biological effects can often be achieved by completely different compounds. However, compounds within a given structural family may exhibit quite different biological activities depending on their interactions with different intracellular proteins like enzymes or receptors. By varying the functional groups and structural elements of a lead compound, its interaction with the active site of the target protein, as well as its physicochemical, pharmacokinetic, and dynamic properties can be improved. In this context, the introduction of fluorine into active ingredients has become an important concept in the quest for a modern crop protection product with optimal efficacy, environmental safety, user friendliness, and economic viability. Fluorinated organic compounds represent an important and growing family of commercial agrochemicals. A number of recently developed agrochemical candidates represent novel classes of chemical compounds with new modes of action; several of these compounds contain new fluorinated substituents. However, the complex structure-activity relationships associated with biologically active molecules mean that the introduction of fluorine can lead to either an increase or a decrease in the efficacy of a compound depending on its changed mode of action, physicochemical properties, target interaction, or metabolic susceptibility and transformation. Therefore, it is still difficult to predict the sites in a molecule at which fluorine substitution will result in optimal desired effects.

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Section: Insecticides Containing Fluorine Pyrethroidesmentioning

confidence: 99%

Section: Insecticides Containing Fluorine Pyrethroidesmentioning

confidence: 99%

The Unique Role of Fluorine in the Design of Active Ingredients for Modern Crop Protection

2004

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“…Triazole is a very popular constituent in the drug discovery and development. Triazole growing interest refers to their known antifungal (fluconazole and itraconazole are marketed examples), herbicidal , and antimicrobial activities .…”

Section: Introductionmentioning

confidence: 99%

Convenient Synthesis of Some Novel Pyridazinone‐Bearing Triazole Moieties

Rayes

Ali

Fathalla

2018

Journal of Heterocyclic Chem

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The chemoselective reactions of 2‐(5‐mercapto‐4‐phenyl‐4H‐[1,2,4]triazol‐3‐ylmethyl)‐6‐p‐tolyl‐4,5‐dihydro‐2H‐pyridazin‐3‐one (3) with different electrophiles were evaluated. Triazole 3 reacted with alkyl halides in the presence of triethylamine in alcohol to give the corresponding S‐substituted derivatives. On the basis of S‐chemoselective reactions of triazole 3, a series of amino acid 10a–d and dipeptide derivatives 12a–d were prepared via azide coupling of the corresponding hydrazides 9 and 15 with amino acid ester hydrochlorides, respectively. N‐Substituted triazoles 6a–c or 7a–d attached to pyridazin‐3‐one moiety were successfully formed by the reaction of 3 with activated acrylic acid derivatives or with amines. Antibacterial activities of the synthesized derivatives were investigated through correlation with Escherichia coli FabH inhibitory activities using molecular modeling docking software. The antimicrobial activity of synthesized compounds was evaluated, showing best inhibition zone for N‐substituted carboxylic acid 5a and N‐substituted nitrile 5c parallel to the molecular modeling studies.

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“…Recently we published an example of a herbicide optimization project 9 . The lead molecule (1) contained 7 non-equivalent positions.…”

Section: Figure 1 a Seven Compound Sequential Simplex Optimization Imentioning

confidence: 99%

Successful Application of the QSAR Paradigm in Discovery Programs

Plummer

1995

ACS Symposium Series

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The Quantitative Structure-Activity Relationship (QSAR) approach, first described by Corwin Hansch and Toshio Fujita thirty years ago, remains central to pesticide design. The successful application of this paradigm in the discovery of new pesticides depends on two key elements: statistical experimental design and effective computational tools. These tools must be available to bench scientists in a form that they can readily apply in the course of their daily design efforts. This report will describe a system that laboratory scientists have used for over ten years in our laboratory. Key components of this system are: • Database tools to automatically integrate physicochemical parameters and biological data • Experimental design tools for application of statistical experimental designs • Analysis tools for pattern recognition and Free-Wilson and regression analysesThe report will illustrate the application of the approach to actual research programs. This will include application of cluster analysis, sequential simplex, and central composite designs to rapidly advance pesticide design projects.Thirty years ago Drs. Corwin Hansen and Toshio Fujita initiated a body of work that has evolved into the current QSAR paradigm 1 . This represented a dramatic shift from the way drugs and pesticides had been discovered; it moved from an intuitive evaluation of the effects of structure change on biological activity to a quantitative, scientifically verifiable evaluation based on accurately measured physical properties and sound statistical principles. Over the years that I have been involved in following and teaching the QSAR Paradigm, the question most asked has been: "Does QSAR really work?" It has become easier for me to answer the question as I see the many ways that QSAR can make Discovery programs more effective. Today I would list QSAR's success criteria as the following: 0097-6156/95/0606-0240$12.00/0

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Synthesis and activity optimization of herbicidal substituted 4-aryl-1,2,4-triazole-5(1H)-thiones

Cited by 21 publications

References 11 publications

The Unique Role of Fluorine in the Design of Active Ingredients for Modern Crop Protection

The Unique Role of Fluorine in the Design of Active Ingredients for Modern Crop Protection

Convenient Synthesis of Some Novel Pyridazinone‐Bearing Triazole Moieties

Successful Application of the QSAR Paradigm in Discovery Programs

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