120740-08-1

Usage

Uses

Used in Pesticide Industry:
2-chloro-5-aminomethylthiazole is used as a metabolite of Thiamethoxam (T344180), a neonicotinoid insecticide. It plays a crucial role in the biological activity and effectiveness of the insecticide in controlling pests, particularly in agricultural settings. The presence of the chloro and aminomethyl groups in the thiazole ring structure contributes to the compound's ability to target and affect the nervous systems of insects, leading to their paralysis and eventual death. This makes it a valuable component in the development and formulation of neonicotinoid-based pesticides for crop protection and other applications.

InChI:InChI=1/C4H5ClN2S/c5-4-7-2-3(1-6)8-4/h2H,1,6H2

Upstream product

• 105827-91-6 α-Cl-β-thiazolyl chloride 
• 120740-09-2 N-(2-chloro-5-thiazolylmethyl)phthalimide 
• 1088445-95-7 5-(azidomethyl)-2-chlorothiazole 
• 1074-82-4 potassium phtalimide 
• 872165-33-8 1,3,5-tris{(2-chloro-1,3-thiazol-5-yl)methyl}-1,3,5-hexahydrotriazine 

Downstream Products

• 210880-92-5 clothianidine 
• 935440-43-0 3-[(2-chlorothiazol-5-yl)methyl]-1-[2-fluoro-4-(trifluoromethylthio)-phenyl]-1-methyl-urea 
• 1416712-48-5 tert-butyl ((2-chlorothiazol-5-yl)methyl)carbamate 

Relevant academic research and scientific papers

Design, Synthesis, and Fungicidal Activity of Novel Imidazo[4,5-b]pyridine Derivatives

A series of novel imidazo[4,5-b]pyridine derivatives were designed and synthesized. The structures of all the newly synthesized compounds were identified by spectroscopic data NMR, MS, and elemental analysis. Bioassay showed that the compounds exhibited potent fungicidal activities against Erysiphe graminis, Puccinia polysora, and so forth. Particularly, 2-chloro-5-((5-methoxy-2-(2-(trifluoromethyl)phenyl)-3H-imidazo[4,5-b]pyridin-3-yl)methyl)thiazole (9b) displayed fungicidal potency against P.?polysora. Its EC50 value: 4.00?mg/L is comparable with that of tebuconazole. The structure–activity relationship for the target compounds is discussed.

Imidazo [4, 5-b] pyridine compounds with biological activity as well as preparation method and application of imidazo [4, 5-b] pyridine compounds

The invention discloses imidazo [4, 5-b] pyridine compounds with biological activity as well as a preparation method and application of the imidazo [4, 5-b] pyridine compounds. The structure of the the imidazo [4, 5-b] pyridine compounds is as shown in a general formula (I), wherein R represents a hydrogen or halogen atom; R1 represents hydrogen or a methyl group; R2 represents hydrogen, a C1-C4 linear or branched alkyl group, or a heterocyclic benzyl group, the heterocyclic ring is a five-membered aromatic heterocyclic ring, and the hydrogen atom on a heterocyclic ring is unsubstituted, optionally substituted by the C1-C4 linear or branched alkyl group, or optionally substituted by the halogen atom; Ar represents a phenyl group, a thienyl group or a thiazolyl group, wherein a hydrogen atom on the ring is unsubstituted, or optionally substituted by a substituent independently selected from a halogen atom, a methoxy group, a methyl group and a halogenated methyl group; X represents O, S, SO or SO2. The compounds shown in the formula (I) have the bactericidal, insecticidal/acaricidal broad-spectrum activity at an amount of 15-5000g of active ingredient per hectare.

HEPATITIS B CORE PROTEIN MODULATORS

The present disclosure provides, in part, compounds having allosteric effector properties against Hepatitis B virus Cp. Also provided herein are methods of treating viral infections, such as hepatitis B, comprising administering to a patient in need thereof a disclosed compound of formula:

Thiazole Methylamino Pyridine Compounds and Preparation Method Therefor

Disclosed are thiazole methylamino pyridine compounds represented by the general formula (I) having fungicidal, insecticidal/acaricidal, and herbicidal activity, the preparation method thereof, the fungicidal, insecticidal/acaricidal, and herbicidal compositions containing the compounds of the present invention, and the use and the method for controlling fungi, insects/acari and weeds of the compounds of the present invention.

Design, synthesis, and particular biological behaviors of chain-opening nitromethylene neonicotinoids with cis configuration

On the basis of the structure of heterocyclic-fused cis configuration derivatives and chain-opening neonicotinoids, two series of novel chain-opening tetrahydropyridine analogues were designed and synthesized. The preliminary bioassay tests were determined on cowpea aphid (Aphis craccivora) and armyworm (Pseudaletia separata Walker). The results showed that some of the target compounds exhibited repellent effects, whereas others showed good insecticidal activities.

PROCESS FOR PRODUCING AN AMINOMETHYL THIAZOLE COMPOUND

A process for producing a thiazole compound of the formula (3): wherein X1 is a hydrogen atom or a halogen atom, which comprises reacting a compound of the formula (1): wherein X1 is as defined above, and X2 represents a halogen atom, with ammonia and formaldehyde to obtain a hexahydrotriazine compound of the formula (2): wherein X1 is as defined above, and reacting the resulting hexahydrotriazine compound with hydroxylamine under acidic conditions. According to this process, the thiazole compound of the formula (3) can be industrially advantageously produced using inexpensive ammonia with suppressing the formation of a byproduct of the formula (4): wherein X1 is as defined above.

COMPOUND FOR PREPARING THIAZOLE BY AMINOMETHYLATION

A process for preparing a thiazole compound of formula (3): wherein X1 represents a hydrogen atom or a halogen atom comprising reacting a compound of formula (1): wherein X1 is as defined above, and X2 represents a halogen atom, with ammonia and formaldehyde to obtain a hexahydrotriazine compound of formula (2): wherein X1 is as defined above, and hydrolyzing the compound of formula (2).

Synthesis and Herbicidal Activity of 2-Cyano-3-(2-chlorothiazol-5-yl)methylaminoacrylates

A series of 2-cyano-3-(2-chlorothiazol-5-yl)methylaminoacrylates were synthesized as herbicidal inhibitors of PSII electron transport. All of these compounds exhibited good herbicidal activities. In particular, (Z)-ethoxyethyl 2-cyano-3-isopropyl-3-(2-chlorothiazol-5-yl)methylaminoacrylate showed excellent herbicidal activities even at a dose of 75 g/ha. A suitable group at the 3-position of acrylate was essential for high herbicidal activity. 2-Cyanoacrylates containing a 2-chloro-5-thiazolyl group are a novel class of herbicides and display herbicidal activities comparable to existing analogues bearing chloropyridyl or chlorophenyl.

Process for the preparation of chlorothiazole derivatives

Novel processes for preparing 2-chlorothiazoles, useful as an intermediate for insecticides, from allyl isothiocyanate derivatives having the formula [II]: STR1 wherein X represents a leaving group, are simple and convenient reaction procedures under mild conditions without need of a large excess of a chlorinating agent. Further, processes for preparing 5-(aminomethyl)-2-chlorothiazole or salts thereof from the compound [II] achieve higher yields by simple, convenient and inexpensive procedures.