7.0 t fticr ms instrument

The melting points were determined on an X-4 binocular microscope apparatus (uncorrected). ¹H NMR spectra were determined at 400 MHz and ¹³C NMR spectra at 101 MHz using a Bruker AV 400 instrument with CDCl₃ or DMSO-d₆ as solvents, and tetramethylsilane as the internal standard. HRMS were determined on a Varian 7.0 T FTICR-MS instrument. The purity analysis of the synthesised compounds were conducted on an Agilent 1260-II high performance liquid chromatography (HPLC) apparatus. Column chromatography was conducted using 200–300 mesh silica gel. Reagents were of analytically pure grade. Solvents were dried and distilled using the standard procedure before use. Benzo[d]thiazol-2-amine, 6-chlorobenzo[d]thiazol-2-amine and 6-(trifluoromethyl)benzo[d]thiazol-2-amine were purchased from J&K Scientific Ltd. Naphthalen-2-ol and partial heteroaryl aldehydes were bought from Tianjin Heowns Business Licence and Bide Pharmatech Ltd. As the positive control for biological tests, chlorantraniliprole was prepared following the known literature procedure²⁶ (link)^,27 . Another two bioassay controls that have the similar structural characteristic as β-naphthol − 1-((benzo[d]thiazol-2-ylamino)(4-methoxyphenyl)methyl)naphthalen-2-ol (viii) and 1-((benzo[d]thiazol-2-ylamino)(4-chlorophenyl)methyl)naphthalen-2-ol (ix), were prepared via the reported literature protocol²⁰ (link).

Metolachlor (emulsifiable concentrate, 960 g/L), substituted fatty acids (purity 97–99%), isobutylamine (purity 99%), 2-methyl allylamine (purity 97%), 1-amino-2-methyl propan-2-ol (purity 98%), chlorotripyrrolidinophosphonium hexafluorophosphate (PyClOP, purity 98%), and N,N-diisopropylethylamine (DIEA, 99%) were purchased from Jilin Chinese Academy of Sciences-Yanshen Technology Co., Ltd. (Jilin, Changchun, China). All solvents were bought from Sinopharm Chemical Reagent Co., Ltd. (Beijing, China) and further distilled before use. Thin-layer chromatography (TLC) was performed with Silicagel GF254 (Merck KGaA, Darmstadt, Germany). The isolation and purification were carried out via silica gel column chromatography (200 mesh). Melting points (Mp) were measured by a Hanon MP100 automatic melting point apparatus (Jinan Hanon Instruments Co., Ltd., Jinan, China) and autocorrected. ¹H NMR and ¹³C NMR were recorded on a Bruker Avance-300 spectrometer operating at 300 MHz (¹H) and 75 MHz (¹³C), respectively, using tetramethylsilane (TMS) as an internal standard (solvent CDCl₃ or DMSO-d₆). Chemical shifts (δ) were reported in parts per million (ppm), and coupling constants (J) were in Hz. HRMS was analyzed on a Varian 7.0 T FTICR-MS instrument (Varian IonSpec, Lake Forest, CA, USA).

All reagents and chemicals were purchased from commercial sources, including 2,5-dimethyl-2,4-dihydro-3H-pyrazol-3-one (2o). ¹H and ¹³C nuclear magnetic resonance (NMR) spectra were recorded using a Bruker Avance-400 spectrometer (Bruker BioSpin AG, Fällanden, Switzerland). Deuterated chloroform (CDCl₃) and deuterated dimethyl sulfoxide (DMSO-d₆) were used as NMR solvents and tetramethylsilane (TMS) was used as an internal standard. Melting points (mp) were recorded on the Hanon MP100 melting point apparatus (Hanon Instruments, Jinan, China). High-resolution mass spectral analysis was carried out using a Varian 7.0 T FTICR-MS instrument (Varian IonSpec, Lake Forest, CA, United States). Single-crystal X-ray data were obtained using a Bruker SMART APEX II X-ray single-crystal diffractometer (Bruker AXS, Karlsruhe, Germany), graphite monochromated Mo Kα radiation (λ = 0.71073 Å), a 3WP-2000-Spray tower (Nanjing Institute of Agricultural Mechanization, Ministry of Agriculture and Rural Affairs, Nanjing, China), and a A560-UV-VIS spectrophotometer (Aoyi Instruments Co., Ltd., Shanghai, China).