Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Oxyranyle-triazoline thiones and their use as microbicides

A technology of oxirane-based and triazolinethione, which is applied in biocides, animal repellents, plant growth regulators, etc., and can solve unsatisfactory problems

Inactive Publication Date: 2004-06-09
BAYER AG
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The activity of the substance is good; however it is sometimes unsatisfactory at low application rates

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Oxyranyle-triazoline thiones and their use as microbicides
  • Oxyranyle-triazoline thiones and their use as microbicides
  • Oxyranyle-triazoline thiones and their use as microbicides

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0241]

[0242] Under stirring at room temperature, 350 mg (0.97 mmol) of 3-(2-chloro-phenyl)-2-(4-fluoro-phenyl)-2-[(4,5-dihydro-5-thiono-1 , 2,4-triazol-1-yl)-methyl]-oxirane, a mixture of 0.1ml triethylamine and 5ml anhydrous tetrahydrofuran was added dropwise with 110mg (0.97mmol) isocyanide in 5ml anhydrous tetrahydrofuran Solution of acid 3-ethoxy-propyl ester. After the addition was complete, the reaction mixture was heated at 60°C for 1 hour, then concentrated under reduced pressure. The product that remains is chromatographed on silica gel using a cyclohexane / ethyl acetate = 4:1 mixture. Concentration of the eluate afforded 390 mg (82% of theory) of the substance of the formula given above.

[0243] 1 H-NMR spectrum (300MHz, CDCl 3 , TMS): δ=10.0(s, 1H); 84(s, 1H); 7.6-7.3(m, 6H); 7.0(t, 2H, J=8.7Hz); 5.1(d, 1H,

[0244] J=14.9Hz); 4.1(s, 1H); 3.7(d, 1H, J=14.9Hz); 3.5-3.4(m, 6H); 1.9-1.8(m,

[0245] 2H); 1.2(t, 3H, J=7.0Hz) ppm.

[0246] The compounds liste...

Embodiment 7

[0251]

[0252] 1 H-NMR spectrum (400MHz, CDCl 3 , TMS): δ=7.8(s, 1H); 7.3-7.1(m, 4H); 7.0-6.9(m, 4H); 6.7(s, 1H); 5.0(d, 1H); 4.7(d, 1H ); 4.5(s, 1H); 3.7(m, 1H); 1.0(d, 6H, J=6.6Hz)ppm.

Embodiment A

[0255] Powdery mildew (Erysiphe) test (barley) / protective

[0256] Solvent: 25 parts by weight of N,N-dimethylacetamide

[0257] Emulsifier: 0.6 parts by weight of alkyl aryl polyglycol ether

[0258] To prepare a suitable preparation of the active compound, 1 part by weight of the active compound is mixed with the stated amount of solvent and emulsifier, and the emulsifiable concentrate is diluted with water to the desired concentration.

[0259] To test for protective activity, young plants are sprayed with the preparation of active compound at the stated application rates.

[0260] After the spray coat has dried on, the plants are sprinkled with spores of wheat powdery mildew (Erysiphe graminis f. sp. hordei).

[0261] The plants are placed in a greenhouse at a temperature of about 20° C. and a relative air humidity of about 80% to promote the growth of mildew spots.

[0262] Evaluations were performed 7 days after inoculation. 0% indicates an efficacy equivalent to t...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

Novel oxiranyl-triazolinethiones of the formula I and Ia in which R1, R2 and R3 are each as defined in the description, a process for preparing the novel substances and their use as microbicides in crop protection and in the protection of materials.

Description

technical field [0001] The present invention relates to novel oxiranyl-triazolinethiones, a process for their preparation and their use as microbicides. Background technique [0002] Various azolylmethyl-oxirane derivatives are known to have fungicidal properties (cf. EP-A0094564, EP-A0196038 and WO-A96-38440). Thus, for example, 3-(2-chloro-phenyl)-2-(4-fluoro-phenyl)-2-[(4,5-dihydro-5-thiono-1,2,4-triazole -1-yl)-methyl]-oxirane can be used to control fungi. The activity of this substance is good; however, it is sometimes unsatisfactory at low application rates. Contents of the invention [0003] Therefore, the present invention provides novel oxirane-triazoline thiones of the following formula [0004] [0005] in [0006] R 1 Represents alkyl having 1-4 carbon atoms, haloalkyl having 1-4 carbon atoms and 1-5 halogen atoms, cycloalkyl having 3-7 carbon atoms optionally substituted by halogen, naphthyl Or optionally by the same or different substituents selected...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): A01N43/653A01N47/38C07D249/12C07D405/06
CPCC07D405/06A01N43/653A01N47/38
Inventor S·希勒布兰德M·尧特拉特A·毛勒-马赫尼克K·斯滕策尔M·库格勒O·埃克斯纳
Owner BAYER AG
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com