(<i>Z</i>)-<i>N</i>-{3-[(6-Chloropyridin-3-yl)methyl]-1,3-thiazolidin-2-ylidene}cyanamide

Gao, Jin‐Sheng; Qiao, Jun; Yu, Ying‐Hui; Hou, Guang-Feng

doi:10.1107/s1600536811013316

Cited by 6 publications

(8 citation statements)

References 2 publications

(2 reference statements)

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“…S1 a, b (Supporting Information)) are the most stable in the gas phase. This result clearly correlates with the experimental determination of the crystallographic structure . The unit cell of thiacloprid crystals is asymmetric, because it is formed by both Z conformers.…”

Section: Discussionsupporting

confidence: 85%

“…), whereas the latter occurs perpendicularly to the same plane. Therefore, since a preferential SERS enhancement is expected for those vibrations which have components perpendicular to the metal surface, the intensity pattern suggests that the N15–C14–N13–C9–S plane (and, as a consequence, the whole ring II which is almost planar) is perpendicular to the surface. A pictorial representation of the relative orientation of thiacloprid and the Ag surface is given in Fig.…”

Section: Discussionmentioning

confidence: 98%

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Surface‐enhanced Raman spectra of the neonicotinoid pesticide thiacloprid

Cañamares

Feis

2013

J Raman Spectroscopy

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Thiacloprid is a widely used pesticide belonging to the neonicotinoid class, which is characterized by a selective activity against insects and a reduced acute toxicity for humans. The importance of the environmental impact of neonicotinoids is being intensively researched, in order to evaluate the danger they pose for useful insects. Physical methods which allow the characterization of neonicotinoids in diluted aqueous solutions are therefore desirable. We present a study of Raman and surface‐enhanced Raman scattering (SERS) spectroscopy on thiacloprid in solid state, in acetone solution, and adsorbed onto silver and gold hydrosols at μM concentration. Density functional theory calculations allow the individualization of the most stable molecular structure, both in gas phase and in solution, and of the corresponding Raman spectra. The vibrational assignments lead to an interpretation of the differences between SERS and ordinary Raman spectra based on the possible interactions between the molecule and the metal surface, the main one involving the iminocyano group. Formation of a charge‐transfer complex is suggested by the dependence of the SERS spectra on the laser excitation wavelength. We evaluate the applicability of SERS spectroscopy to the chemical analysis of thiacloprid comparing SERS with current analytical methods. Copyright © 2013 John Wiley & Sons, Ltd.

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Section: Discussionsupporting

confidence: 85%

Section: Discussionmentioning

confidence: 98%

Surface‐enhanced Raman spectra of the neonicotinoid pesticide thiacloprid

Cañamares

Feis

2013

J Raman Spectroscopy

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“…Form I ( Figure 6 and Figure 7 A) crystallized as blocks in the monoclinic space group P 2 1 / c , Z = 4, Z ’ = 1 (See Table 1 ). The structure of Form II ( Figure 6 and Figure 7 B), grown as needles, was reported previously, and confirmed here as the monoclinic space group P 2 1 / c , Z = 8, Z ’ = 2 [ 28 ]. The concentric bands, a consequence of helicoidal twisting of crystallites growing radially, is a common phenomenon among melt-grown molecular crystals, which we have documented thoroughly [ 29 , 30 , 31 , 32 , 33 ].…”

Section: Resultssupporting

confidence: 88%

Crystallography of Contemporary Contact Insecticides

Erriah

Zhu

et al. 2022

Insects

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The active forms of contact insecticides used for combatting mosquito-borne infectious diseases are typically crystalline solids. Numerous molecular crystals are polymorphic, crystallizing in several solid forms characterized by different physicochemical properties, including bioavailability. Our laboratory recently found that the activity of crystalline contact insecticides is inversely dependent on the thermodynamic stability of their polymorphs, suggesting that efficacy can be enhanced by the manipulation of the solid-state structure. This paper argues that crystallography should be central to the development of contact insecticides, particularly because their efficacy continues to be compromised by insecticide resistance, especially among Anopheles mosquito populations that spread malaria. Although insecticidal compounds with new modes of action have been introduced to overcome resistance, new insecticides are expensive to develop and implement. The repurposing of existing chemical agents in metastable, more active crystalline forms provides an inexpensive and efficient method for ‘evergreening’ compounds whose risks are already well-established. We report herein seven new single-crystal structures of insecticides used for controlling infectious disease vectors. The structures reported herein include pyrethroid insecticides recommended by the WHO for indoor residual spraying (IRS)-bifenthrin, β-cyfluthrin, etofenprox, α-cypermethrin, and λ-cyhalothrin as well as the neonicotinoid insecticide thiacloprid.

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“…62 THIA-2 and THIA-4 conformers are similar to EXP-1 and EXP-2, respectively. 62 THIA-2 and THIA-4 conformers are similar to EXP-1 and EXP-2, respectively.…”

Section: Thiaclopridmentioning

confidence: 80%