From 2000 to mid-2010: a fruitful decade for the synthesis of pyrazoles.

1,3,4-Thiadiazole: Synthesis, Reactions, and Applications in Medicinal, Agricultural, and Materials Chemistry

The present invention relates to compositions, in particular within a fungicide composition, which comprises (A) a dithiino-tetracarboximide of formula (I) and a further fungicidally active compound (B). Moreover, the invention relates to a method for curatively or preventively controlling the phytopathogenic fungi of plants or crops, to the use of a combination according to the invention for the treatment of seed, to a method for protecting a seed and to the treated seed.

Active compound combinations

Sulfoxaflor and the sulfoximine insecticides: Chemistry, mode of action and basis for efficacy on resistant insects

1,4,2-Dioxazol-5-ones are five-membered heterocycles known to decarboxylate under thermal or photochemical conditions, thus yielding N-acyl nitrenes. Described herein is a light-induced ruthenium-catalyzed N-acyl nitrene transfer to sulfides and sulfoxides by decarboxylation of 1,4,2-dioxazol-5-ones at room temperature, thus providing direct access to N-acyl sulfimides and sulfoximines under mild reaction conditions. In addition, a one-pot sulfur imidation/oxidation sequence catalyzed by a single ruthenium complex is reported.

Light‐Induced Ruthenium‐Catalyzed Nitrene Transfer Reactions: A Photochemical Approach towards N‐Acyl Sulfimides and Sulfoximines

A series of novel pyrazole oxime derivatives containing a 2-chloro-5-thiazolyl moiety were synthesized. Their structures were confirmed by (1)H NMR, (13)C NMR, and elemental analysis. The preliminary bioassays showed that all of the title compounds had low acaricidal activity against Tetranychus cinnabarinus . However, most of them exhibited excellent insecticidal activity against Aphis medicagini at the dosage of 0.5 mg/mL, and some compounds still showed good insecticidal activity against A. medicagini even at the dosage of 0.2 mg/mL. Meanwhile, some title compounds displayed fungicidal and plant growth regulatory activities.

Synthesis and Biological Activities of Novel Pyrazole Oxime Derivatives Containing a 2-Chloro-5-thiazolyl Moiety

The N-substituted alkyl sulfoximine derivatives are a new chemical family of neonicotinoid insecticides. We have designed and synthesized 10 (1,3-thiazole)alkyl sulfoximine derivatives. All compounds were identified by (1)H and (13)C nuclear magnetic resonance (NMR), IR, and elemental analyses. Preliminary bioassays indicated that some title compounds exhibited good insecticidal activities at 10 mg/L against Myzus persicae . The relationship between structure and biological activity was also discussed.

Synthesis and insecticidal activity of N-substituted (1,3-thiazole)alkyl sulfoximine derivatives.

A variety of novel 3-trifluoromethyl substituted pyrazole oxime ether derivatives containing a pyridyl moiety were designed and synthesized in satisfactory yields. Their structures were confirmed by H NMR, C NMR, and elemental analysis. The preliminary bioassays indicated that some of the title compounds showed potential insecticidal activities against Aphis craccivora, and some compounds also displayed plant growth regulatory activities.

Synthesis and bioactivities of novel trifluoromethylated pyrazole oxime ether derivatives containing a pyridyl moiety

Three series of novel 2-cyanoacrylates 7a–7f, 9a–9f, 10a–10f containing 1,3,4-thiadiazole ring moieties were synthesized as herbicidal inhibitors of photosystem II (PS II) electron transportation. Their structures were clearly verified by 1H NMR, 13C NMR, elemental analysis (or HRMS analysis) and single-crystal X-ray diffraction analysis. Bioassay showed that a suitable group at the 3-position of acrylates was essential for high herbicidal activity. In particular, compound 7e showed the best herbicidal activities and gave 100% inhibitory activity against rape and amaranth pigweed at a dose of 1.5 kg/ha. Introduction of substituent with higher polarity such as sulfinyl or sulfonyl to the 5-position of 1,3,4-thiadiazole decreased herbicidal activities.

Xue Qin

Papers

Synthesis and Biological Activities of Novel Pyrazole Oxime Derivatives Containing a 2-Chloro-5-thiazolyl Moiety

Synthesis and insecticidal activity of N-substituted (1,3-thiazole)alkyl sulfoximine derivatives.

Synthesis and bioactivities of novel trifluoromethylated pyrazole oxime ether derivatives containing a pyridyl moiety

Synthesis, Crystal Structure, and Herbicidal Activities of 2‐Cyanoacrylates Containing 1,3,4‐Thiadiazole Moieties

Synthesis and herbicidal activities of 2-cyano-3-benzylaminoacrylates containing thiazole moiety.