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Fluorotriazine compound with herbicidal activity and its preparation method

A fluorotriazine and compound technology, applied in the field of fluorotriazine compounds and their preparation, can solve the problems of not providing test data, no report on biological activity, no test data, etc., reducing energy consumption, The effect of avoiding high temperature reaction and increasing safety

Active Publication Date: 2014-07-02
中国中化股份有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The preparation method disclosed in this patent is to directly react chlorotriazine and potassium fluoride at high temperature to obtain the corresponding fluorotriazine compound. The patent indicates that the prepared compound has biological activity, but no test data is given
GB872313 (1961) also discloses some substituted fluorotriazine compounds. The preparation method is to use cyanuric fluoride to react with organic amines to prepare target compounds. The patent mentions that the obtained compounds can be used as fungicides and herbicides, but No corresponding test data provided
However, in the prior art, the fluorotriazine compounds with alicyclic substituents and their biological activity as shown in the present invention have not been reported.

Method used

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  • Fluorotriazine compound with herbicidal activity and its preparation method
  • Fluorotriazine compound with herbicidal activity and its preparation method
  • Fluorotriazine compound with herbicidal activity and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Example 1: N-cyclohexyl-6-fluoro-N-isopropyl-1,3,5-triazine-2,4-diamine (compound 1)

[0060]

[0061] 2.70 grams (0.02mol) of cyanuric fluoride and 2.76 grams (0.02mol) of potassium carbonate were added to a reaction vessel filled with 20 milliliters of tetrahydrofuran, and the mixed solution was cooled to -10°C in an ice-salt bath, and 1.18 grams of ( 0.02mol) of isopropylamine in 5 milliliters of tetrahydrofuran solution, keeping the temperature at -5°C all the time, and continuing to insulate and stir the reaction for 2 hours. After the reaction was detected by TCL, the salt was removed by filtration, and the filtrate was precipitated under reduced pressure to obtain 2.85 grams of white crystal 4,6-difluoro-N-isopropyl-1,3,5-triazine-2-diamine, with a yield of 82.8 %, mp: 73-75°C.

[0062] The above white crystal (4,6-difluoro-N-isopropyl-1,3,5-triazine-2-diamine) was added into a reaction vessel containing 10 ml of acetone, and the temperature was raised to 30°...

Embodiment 2

[0063] Example 2: N-cyclopropyl-6-fluoro-N-isopropyl-1,3,5-triazine-2,4-diamine (compound 5)

[0064]

[0065] 2.70 grams (0.02mol) of cyanuric fluoride and 2.76 grams (0.02mol) of potassium carbonate were added to a reaction vessel containing 20 milliliters of toluene, and the mixed solution was cooled to -10°C in an ice-salt bath, and 1.18 grams of ( 0.02mol) of isopropylamine in 10 ml of toluene solution, keep the temperature at -5°C all the time, continue to insulate and stir the reaction for 2 hours. After the reaction was detected by TCL, the salt was removed by filtration, and the filtrate was precipitated under reduced pressure to obtain 2.85 grams of white crystal 4,6-difluoro-N-isopropyl-1,3,5-triazine-2-diamine, with a yield of 82.8 %, mp: 73-75°C.

[0066] The above white crystal (4,6-difluoro-N-isopropyl-1,3,5-triazine-2-diamine) was added into a reaction vessel containing 20 ml of toluene, and the temperature was raised to 30°C. 5 ml of a toluene solution co...

Embodiment 3

[0067] Example 3: N-cyclopropyl-6-fluoro-N-(1-methylcyclopropyl)-1,3,5-triazine-2,4-diamine (compound 25)

[0068]

[0069] Add 2.70 grams (0.02mol) of cyanuric fluoride and 0.8 grams (0.02mol) of sodium hydroxide into a reaction vessel containing 20 milliliters of dichloromethane, cool the mixed solution to -10°C in an ice-salt bath, and add dropwise 1.18 g of cyclopropylamine in 10 ml of dichloromethane solution, the temperature was kept at -5°C, and the reaction was then incubated and stirred for 2 hours, and no raw materials were detected by HPLC. The salt was filtered off, and the solvent was precipitated under reduced pressure to obtain 3.19 g of white crystal N-cyclopropyl-4,6-difluoro-1,3,5-triazin-2-amine, yield 92.7%, mp: 86~88°C .

[0070] Add the above-mentioned white crystal N-cyclopropyl-4,6-difluoro-1,3,5-triazin-2-amine into a 100 ml round bottom flask, add 30 ml of acetone as a solvent, and heat up to 30°C. Add dropwise 5 milliliters of acetone solution ...

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PUM

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Abstract

Belonging to the field of agricultural herbicides, the invention specifically discloses a fluorotriazine compound with herbicidal activity or its ammonium salt, as well as preparation and application of the compound. The compound of the invention has a structure as shown in general formula I, wherein, the definition of each group can be found in the specification. With good herbicidal activity, the compound of the invention can effectively control monocotyledonous and dicotyledonous weeds before and after the emergence of seedlings.

Description

technical field [0001] The invention belongs to the field of agricultural herbicides, and in particular relates to a fluorotriazine compound with herbicidal activity and a preparation method thereof. Background technique [0002] Ciba-Geigy, Switzerland first synthesized Atrazine, the first triazine herbicide, in 1952, and then several chlorotriazine herbicide varieties came out one after another. Chlorotriazine herbicides have the following structures: [0003] [0004] This type of herbicide is mainly used for weeding in corn fields, and has the advantages of effectively controlling a variety of broad-leaved, monocotyledonous, annual and perennial weeds. Since the weeds will develop resistance to the chlorotriazine herbicides or their compositions after being used for a period of time, and the chlorotriazine herbicides are not easily degraded in soil, causing phytotoxicity to the next crops. Accordingly, there is a continuing need to invent new and improved herbicidal...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D251/50A01N43/70A01P13/00
Inventor 王瑛王景国李学敏刘君丽林长福尉宏伟苗雨
Owner 中国中化股份有限公司