Pyrimidine diketone compounds containing benzoxazine ring and application thereof

A kind of technology of pyrimidinedione and benzoxazine ring, applied in the field of pyrimidinedione compound, can solve the problems such as unsuccessful development

Active Publication Date: 2016-01-27
HUAZHONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, commercialized protoporphyrinogen oxidase inhibitors are all developed by major pesticide companies in Europe and America, and there is no report of successful development in China

Method used

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  • Pyrimidine diketone compounds containing benzoxazine ring and application thereof
  • Pyrimidine diketone compounds containing benzoxazine ring and application thereof
  • Pyrimidine diketone compounds containing benzoxazine ring and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0097] This example is used to illustrate the preparation method of the pyrimidinedione compound containing benzoxazine ring of the present invention, which is carried out according to the following synthetic route:

[0098]

[0099] 1) Synthesis of compound 2

[0100] In a 250mL round-bottomed flask, 50mmol of 2,4-difluoroaniline was dissolved in 120mL of redistilled dichloromethane and stirred, and 100mmol of pyridine was added under ice-bath conditions as an acid-binding agent. Subsequently, 50 mmol of ethyl chloroformate was dissolved in 30 mL of redistilled dichloromethane and added dropwise within 30 min. After reacting for about 1 h, it was detected by TLC that the starting material disappeared. The reaction system was neutralized to neutral with 2 mol / L hydrochloric acid, the lower organic phase was extracted, dried with anhydrous sodium sulfate, filtered, solvent removed, and compound 2 was obtained by recrystallization with petroleum ether.

[0101] 2) Synthesis...

Embodiment 2

[0133] This example is used to illustrate the preparation method of the pyrimidinedione compound containing benzoxazine ring of the present invention

[0134] According to the method in Example 1, the difference is that in step 1, 2,4-difluoroaniline is replaced by 2,4-dichloroaniline to obtain the target compounds I-21~I-40 shown in Table 1 , and its yield is shown in Table 1.

[0135] The confirmed data of compounds I-21~I-40 are as follows:

[0136] I-21: solid; m.p.87-89°C. 1 HNMR (600MHz, CDCl 3 )δ7.21(s,1H),6.65(s,1H),6.36(s,1H),4.73(s,2H),4.59(s,2H),4.21(q,J=7.2Hz,2H), 3.56(s,3H),1.23(t,J=7.2Hz,3H).EI-MS:461.16(M + ).

[0137] I-22: solid; m.p.56-57°C. 1 HNMR (600MHz, CDCl 3 )δ7.19(s,1H),6.92(s,1H),6.38(s,1H),4.66(s,2H),4.19-4.11(m,4H),3.58(s,3H),2.66(t , J=7.2Hz, 2H), 1.24(t, J=7.2Hz, 3H).EI-MS: 475.18(M + ).

[0138] I-23: solid; m.p.47-48°C. 1 HNMR (600MHz, CDCl 3 )δ7.18(s,1H),7.04(s,1H),6.38(s,1H),4.65(s,2H),4.12(q,J=7.2Hz,2H),3.92(t,J=7.2 Hz, 2H), 3.58...

Embodiment 3

[0157] This example is used to illustrate the preparation method of the pyrimidinedione compound containing benzoxazine ring of the present invention

[0158] According to the method in Example 1, the difference is that 2,4-difluoroaniline is replaced by 2-bromo-4-fluoroaniline in step 1 to obtain the target compounds I-41~I- 60, and the yields are shown in Table 1.

[0159] The confirmed data of compounds I-41~I-60 are as follows:

[0160] I-41: solid; m.p.67-68°C. 1 HNMR (600MHz, CDCl 3 )δ7.37(s,1H),6.65(s,1H),6.36(s,1H),4.73(s,2H),4.59(s,2H),4.20(q,J=7.2Hz,2H), 3.56(s,3H),1.23(t,J=7.2Hz,3H).EI-MS:505.09(M) + .

[0161] I-42: solid; m.p.69-71°C. 1 HNMR (600MHz, CDCl 3 )δ7.34(s,1H),6.92(s,1H),6.38(s,1H),4.66(s,2H),4.17-4.12(m,4H),3.58(s,3H),2.66(t , J=7.2Hz, 2H), 1.24(t, J=7.2Hz, 3H).ESI-MS: 542.1(M+Na) + .

[0162] I-43: solid; m.p.57-59°C. 1 HNMR (600MHz, CDCl 3 )δ7.33(s,1H),7.05(s,1H),6.39(s,1H),4.65(s,2H),4.12(q,J=7.2Hz,2H),3.92(t,J=7.2 Hz, 2H), 3.58(s, 3H), ...

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Abstract

The invention discloses a kind of pyrimidine diketone compounds containing a benzoxazine ring and application thereof. The pyrimidine diketone compounds containing the benzoxazine ring are compounds with the structure shown as a general formula (1) in the specification, and in the formula (1), R1 is selected from hydrogen or an alkyl with the carbon atom number of 1-6, R2 is an ester with the carbon atom number of 2-10, and X is selected from halogen. The pyrimidine diketone compounds containing the benzoxazine ring possess high weeding activity.

Description

technical field [0001] The invention relates to a pyrimidinedione compound containing a benzoxazine ring and its application. Background technique [0002] Protoporphyrinogen oxidase inhibitors (protox / PPO inhibitors) are a class of herbicides with a special mechanism of action. Phyrinogen IX rapidly accumulates and overflows into the cytoplasm, and becomes photosensitive protoporphyrin IX under the action of non-enzymatic mechanisms or other enzymes. Protoporphyrin IX absorbs energy under the action of light to become an excited state, and transfers energy to Oxygen molecules, making it into singlet oxygen O 1 , Under the action of singlet oxygen, the cell membrane undergoes peroxidation reaction and is destroyed, which causes cell death and eventually leaves death. Due to the unique mechanism of action of protoporphyrinogen oxidase inhibitors, resistance is slow to develop. At the same time, this type of herbicide has a very broad-spectrum herbicidal activity and can con...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/04A01P13/00
Inventor 杨光富左炀
Owner HUAZHONG NORMAL UNIV
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