Thiadiazole compound as well as preparation and application thereof

A technology of thiadiazoles and compounds, applied in the field of thiadiazoles

Inactive Publication Date: 2011-12-14
杭州云图化学科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, there is no information about 5-(5-(substituted benzylthio)-4-cyclopropyl-4H-1,2,4-triazolyl)-4-methyl-1,2,3-thiadiazole Literature Reports on the Synthesis of Derivatives and Their Biological Activities

Method used

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  • Thiadiazole compound as well as preparation and application thereof
  • Thiadiazole compound as well as preparation and application thereof
  • Thiadiazole compound as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1: the synthesis of target compound

[0024] Add 2mmol 4-cyclopropyl-5-(4-methyl-1,2,3-thiadiazol-5-yl)-4H-1,2,4-triazole-3-sulfur to a 25mL round bottom flask Alcohol (II), 2mmol substituted benzyl chloride (III), 8mL DMF and 2.4mmol of K 2 CO 3 , stirred at room temperature, and TLC was used to detect the progress of the reaction. After the reaction was completed, the reaction solution was poured into 30 mL of ice water, and the solid was precipitated, filtered, precipitated, and subjected to silica gel column chromatography to obtain a solid product (see Table 1 and Table 2 for the physical and chemical parameters and mass spectrometry data of the target compound).

[0025]

[0026] Table 1: Physicochemical parameters of target compounds

[0027]

[0028]

[0029] Table 2: Target compounds 1 H NMR data

[0030]

[0031]

Embodiment 2

[0032] Example 2: Herbicidal Activity Test

[0033] (1) Rapeseed plate method:

[0034] Spread a piece of filter paper with a diameter of 5.6 cm in a petri dish with a diameter of 6 cm, add 2 ml of a certain concentration of the test compound solution, and sow 10 rapeseed seeds soaked for 4 hours. The radicle length was measured after 72 hours of dark cultivation at 28±1°C. The herbicidal activity of the compounds was detected by the growth inhibition of the radicles of rapeseed under dark conditions. Test concentration: 10 μg / mL and 100 μg / mL. Each treatment was repeated twice. Activity index: radicle elongation inhibition rate (%). Activity grading indicators: Grade A: ≥80%; Grade B: 60-79%; Grade C: 40-59%; Grade D: ≤39%.

[0035] (2) Barnyard grass small cup method:

[0036] After laying glass beads and filter paper in the small beaker of 50 milliliters, add 6 milliliters of the test compound solution of certain concentration, sow 10 barnyardgrass seeds that just dew...

Embodiment 3

[0041] Embodiment 3: Bactericidal activity test

[0042] 1. Test conditions

[0043] 1.1 Crops and targets

[0044] Test crop: cucumber (Cucumis sativus L.), variety: Xintaimici.

[0045] Test objects: cucumber scab (Cladosporium cucumerinum) spore suspension, cucumber brown spot (Corynespora cassiicola) spore suspension, cucumber sclerotinia (Sclerotinia sclerotiorum (Lib.) de Bary) toxic medium method, cucumber powdery mildew ( Erysiphe cichoracearum) spore suspension, cucumber anthracnose (Colletotrichum orbitale (Berk a L Mont) Arx.).

[0046] 1.2 Environmental conditions

[0047] Cucumber seedlings are at the stage of 2 cotyledons.

[0048] 2. Experimental Design and Arrangement

[0049] 2.1 Test drug

[0050] 2.1.1 Test agents and treatment doses

[0051] The entrusting unit provides 139 test samples, and each sample has a test concentration of 500mg / L.

[0052] 2.1.2 Control drug

[0053] The concentration of Zhongshengmycin control agent was also set at 500mg / ...

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PUM

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Abstract

The invention provides a 5-(5-substituted benzylthio)-4-cyclopropyl-4H-1,2,4-triazolyl)-4-methyl-12,3-thiadiazole derivative (I) as well as a preparation method and application thereof. The derivative has good prevention and treatment effect to cucumber downy mildew, cucumber angular leaf spot, cucumber fusarium wilt, sphaerotheca fuligenea, tomato bacterial leaf spot, rice sheath blight and the like, and has a wide application prospect.

Description

(1) Technical field [0001] The present invention relates to a kind of thiadiazole compound namely 5-(5-(substituted benzylthio)-4-cyclopropyl-4H-1,2,4-triazolyl)-4-methyl-1,2 , 3-thiadiazole derivatives and their preparation and application. (2) Background technology [0002] Heterocyclic compounds have become the mainstream in the development of new pesticides, and in heterocyclic compounds, nitrogen-containing heterocycles are the main ones. Triazoles and thiadiazoles are a category that has developed rapidly in recent years, and many commercial insecticides, fungicides, and herbicides belong to this category. For example, the systemic insecticide thiazophos developed by Ishihara Industry Company of Japan has a strong ability to kill various pests that have developed resistance to traditional insecticides; Fenconazole is a systemic fungicide that inhibits the formation of infected filaments on epispora and prevents rice blast. [0003] However, there is no information a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/04A01N43/828A01P13/00A01P3/00
Inventor 刘幸海李正名谭成侠翁建全李宝聚石延霞刘会君曹耀艳
Owner 杭州云图化学科技有限公司
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