Synthesis and Herbicidal Activity of Fused Δ&lt;sup&gt;2&lt;/sup&gt;-1, 2, 4-Thiadiazolines

Hagiwara, Kazuyoshi; Saitoh, Kenji; Iihama, Teruyuki; Kawana, Takashi; Hosaka, Hideo

doi:10.1584/jpestics.18.4_309

Cited by 12 publications

(4 citation statements)

References 3 publications

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“…In this context, thiazolothiadiazoles and oxazolothiadiazoles have drawn considerable attention, as compounds of this type possess a wide range of pharmacological activities such as antimicrobial, antitubercular, anticancer, anticonvulsant, and herbicidal properties ( Figure 2). 5,16,[50][51][52] The linking position and the nature of the substituents affect both the potency and the toxicity of the compounds, especially when various functional groups that interact with biological receptors are present. The anticonvulsant activity arises mainly through inhibition of the flow of sodium ions into nerve cells.…”

Section: Biological Applicationsmentioning

confidence: 99%

“…[1][2][3] Furthermore, compounds in this group show a range of biological activities, including antibacterial, antifungal, and herbicidal activities. 4,5 Bakr F. We recently published two reviews on the synthesis of heterocyclic compounds containing pyrazolothiazole and thiazolotriazole moieties. 6,7 On the basis of our previous work and our interest in bridgehead-nitrogen heterocyclic systems, we present the first survey of the literature on synthetic routes to various thiazolothiadiazoles and thiazolooxadiazoles.…”

Section: Introductionmentioning

confidence: 99%

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Thiazolothiadiazoles and Thiazolooxadiazoles: Synthesis and Biological Applications

Abdel‐Wahab

Shaaban

2014

Synthesis

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Recent advances in the diversity of synthetic routes available for the preparation of thiazolothiadiazoles and thiazolooxadiazoles are summarized and reviewed. The relative arrangements of the sulfur, oxygen, and nitrogen atoms and the various positions for fusion between the thiazole or oxazole and thiadiazole rings afford four different subclasses of thiazolothiadiazoles and thiazolooxadiazoles. Methods for synthesizing each of these subclasses are discussed separately. These compounds possess antimicrobial, antitubercular, anticancer, and anticonvulsant activities. The observed biological activities are due to the presence of the thiadiazole moiety, which displays diverse pharmacological activities. This short review can serve as a guide for synthetic and medicinal chemists wishing to develop novel thiazolothiadiazoles and thiazolooxadiazoles that can be evaluated as potential drugs.

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Section: Biological Applicationsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Thiazolothiadiazoles and Thiazolooxadiazoles: Synthesis and Biological Applications

Abdel‐Wahab

Shaaban

2014

Synthesis

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“…1. 2 Preparation of 2-(4-chlorophenyl)-5 (2,6 dif uorophenyl)-z14-1, 2, 4-oxadiazolin-3-one (33) A solution of N-(4-chlorophenyl)hydroxyl-amine (0. 75 g, 5.…”

Section: Preparation Of 2-(4-chlorophenyl)-5-(2 6-mentioning

confidence: 99%

“…In the previous paper, we have already described the synthesis and fungicidal activities of 5-arylimino-43-1, 2, 4-thiadiazolines, and on the way to the synthetic development of these series of compounds, we found a new synthetic route to yield 3-arylimino-42-1, 2, 4thiadiazolo-f used heterocycles which showed herbicidal activities. 2 We then tried to synthesize 44-1, 2, 4-thiadiazoline derivatives, the other isomeric 1, 2, 4-thiadiazolines, and investigate their biological activities. closure of 1-thiobenzoyl-3-phenylureas.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Insecticidal Activity of Δ<sup>4</sup>-1, 2, 4-Thiadiazolin-3-ones

et al. 1994

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2, 5Diphenyl-44-1,2,4-thiadiazolin-3-one synthesized and their insecticidal activit were examined. These compounds exhibited disruption of larval molting and ovicidal actions, similar to the function of benzoylphenylurea insecticides. Substituent effect the benzene ring on the insecticidal activity similar to that of benzoylphenylureas. The introduction of fluorine atom the aniline moiety markedly enhanced the activity. The potency of the insecticidal activities 1, 2, 4-thiadiazolin-3-ones against the larvae of Pseudaletia separata Spodoptera litura were almost the same as benzoylphenylureas, but their ovicidal activity against S, was lower than that of benzoylphenylureas. 2, 5-Diphenyl-44-1, 2, 4-oxadiazolin-3-ones also synthesized, and their insecticidal activity decreased compared with of 44-1, 2, 4-thiadiazolin-3-ones. Metabolism of a 44-1, 2, 4thiadiazolin-3-one derivative investigated by feeding the compound to S. litura and a benzoylphenylurea derivative detected as a metabolite in the homogenized insect one day after the feeding. This result suggest that 44-1, 2, 4-thiadiazolin-3-ones were partly metabolized into benzoylphenylureas in insect body and consequently exhibited the insecticidal activity. * Synthesis and Biological Activity of 1, 2, 4-Thiadiazolines (Part 3). For Part 1 and 2, see Refs. 1) and 2), respectively.

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Structure-Activity Relationship and Molecular Design of Peroxidizing Herbicides with Cyclic Imide Structures and Their Relatives

Fujita¹,

Nakayama

1999

Peroxidizing Herbicides

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Synthesis and Herbicidal Activity of Fused Δ<sup>2</sup>-1, 2, 4-Thiadiazolines

Cited by 12 publications

References 3 publications

Thiazolothiadiazoles and Thiazolooxadiazoles: Synthesis and Biological Applications

Thiazolothiadiazoles and Thiazolooxadiazoles: Synthesis and Biological Applications

Synthesis and Insecticidal Activity of Δ<sup>4</sup>-1, 2, 4-Thiadiazolin-3-ones

Structure-Activity Relationship and Molecular Design of Peroxidizing Herbicides with Cyclic Imide Structures and Their Relatives

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