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Synthesis and insecticidal activities of novel N-sulfenyl-N'-tert-butyl-N,N'-diacylhydrazines. 2. N-substituted phenoxysulfenate derivatives. 2008

Qiqi Zhao, and Jian Shang, and Zhiqiang Huang, and Kaiyun Wang, and Fuchun Bi, and Runqiu Huang, and Qingmin Wang
State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry,Nankai University, Tianjin 300071, People's Republic of China.

A series of novel N-substituted phenoxysulfenyl- N'- tert-butyl- N, N'-diacylhydrazines were designed and synthesized as insect growth regulators via the key intermediates N-chlorosulfenyl- N'- tert-butyl- N, N'-diacylhydrazines. Compared to the parent compounds, these N-substituted phenoxysulfenyl derivatives displayed better solubility and improved hydrophobicities. The insecticidal activities of the new compounds were evaluated. The results of bioassays showed that the title compounds possessed a combination of strong stomach as well as contact poison property higher than the corresponding parent compounds. In particular, N-(4-chlorophenoxy)sulfenyl -N'- tert-butyl- N-4-ethylbenzoyl- N'-3,5-dimethylbenzoylhydrazide ( IIIi) as a field testing candidate has higher stomach toxicities against oriental armyworm and tobacco cutworm than the corresponding parent compound RH-5992. Furthermore, the compound IIIi exhibits higher contact activities against Asian corn borer, tobacco cutworm, and cotton bollworm than RH-5992.

UI MeSH Term Description Entries
D007306 Insecticides Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics. Insecticide
D009036 Moths Insects of the suborder Heterocera of the order LEPIDOPTERA. Antheraea,Giant Silkmoths,Giant Silkworms,Silkmoths, Giant,Silkworms, Giant,Antheraeas,Giant Silkmoth,Giant Silkworm,Moth,Silkmoth, Giant,Silkworm, Giant
D006834 Hydrazines Substituted derivatives of hydrazine (formula H2N-NH2). Hydrazide
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D001681 Biological Assay A method of measuring the effects of a biologically active substance using an intermediate in vivo or in vitro tissue or cell model under controlled conditions. It includes virulence studies in animal fetuses in utero, mouse convulsion bioassay of insulin, quantitation of tumor-initiator systems in mouse skin, calculation of potentiating effects of a hormonal factor in an isolated strip of contracting stomach muscle, etc. Bioassay,Assay, Biological,Assays, Biological,Biologic Assay,Biologic Assays,Assay, Biologic,Assays, Biologic,Bioassays,Biological Assays
D013270 Stomach An organ of digestion situated in the left upper quadrant of the abdomen between the termination of the ESOPHAGUS and the beginning of the DUODENUM. Stomachs
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D057927 Hydrophobic and Hydrophilic Interactions The thermodynamic interaction between a substance and WATER. Hydrophilic Interactions,Hydrophilic and Hydrophobic Interactions,Hydrophilicity,Hydrophobic Interactions,Hydrophobicity,Hydrophilic Interaction,Hydrophilicities,Hydrophobic Interaction,Hydrophobicities,Interaction, Hydrophilic,Interaction, Hydrophobic,Interactions, Hydrophilic,Interactions, Hydrophobic

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