Thiotriazinone isoxazoline compound, preparation method and application thereof, protoporphyrinogen oxidase inhibitor and herbicide

A technology containing thiotriazinone and isoxazoline, which is applied in the field of pesticides, can solve the problems that cannot be applied to the growth process of crops, and achieve good herbicidal activity, high crop safety, and the effect of weed removal

Active Publication Date: 2020-11-20
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although the herbicide with this structure has a good weeding effect, it is foreseeable that weeds will also develop resistance to this herbicide in the near future
[0005] In addition, most of the existing herbicides (including the herbicides of the above-mentioned structure disclosed in CN105753853A) not only have an inhibitory effect on weeds, but also have a strong inhibitory effect on crops
This makes these herbicides unsuitable for crop growth

Method used

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  • Thiotriazinone isoxazoline compound, preparation method and application thereof, protoporphyrinogen oxidase inhibitor and herbicide
  • Thiotriazinone isoxazoline compound, preparation method and application thereof, protoporphyrinogen oxidase inhibitor and herbicide
  • Thiotriazinone isoxazoline compound, preparation method and application thereof, protoporphyrinogen oxidase inhibitor and herbicide

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Experimental program
Comparison scheme
Effect test

specific Embodiment approach

[0047] for R 5 , preferably, R 5 is selected from H, halogen or -CN; more preferably, R 5 is selected from halogen or -CN. According to a specific embodiment of the present invention, R 5 selected from -Cl or -CN.

[0048] for R 6 , preferably, R 6 is selected from H, halogen or -CN. According to a specific embodiment of the present invention, R 6 for H.

[0049] for R 7 , preferably, R 7 Choose from H, C 1 -C 6 Alkyl or C 1 -C 8 Haloalkyl; more preferably, R 7 selected from H, -CH 3 , -CH 2 CH 3 or halomethyl. According to a specific embodiment of the present invention, R 7 selected from H or -CH 3 .

[0050] for R 8 , preferably, R 8 Choose from H, C 1 -C 6 Alkyl, C 1 -C 8 Haloalkyl; more preferably, R 8 selected from H, -CH 3 , -CH 2 CH 3 or halomethyl. According to a specific embodiment of the present invention, R 8 selected from H or -CH 3 .

[0051] for R 9 , preferably, R 9 selected from H, -CN, C 1 -C 6 Alkyl, C 1 -C 6 Haloalkyl...

Embodiment approach

[0104] According to a preferred embodiment of the present invention, the condensation reaction comprises the following steps:

[0105] The first step: in the presence of the third solvent, the R 10 A compound represented by the formula (I) of -CO-OH is subjected to an acyl chloride reaction with an acyl chloride reagent to obtain an acyl chloride intermediate;

[0106] Second step: in the presence of the fourth solvent and the third base, the acid chloride intermediate and Structures of compounds undergo chemical reactions.

[0107] In the first step, preferably, the R 10 The molar ratio of the compound represented by the formula (I) which is -CO-OH to the acid chloride reagent is 1:(1.05-3).

[0108] In the first step, preferably, the process of the acid chloride reaction includes the following two stages, wherein stage 1-1 is: at 0-5°C, the third solvent, R 10The compound represented by the formula (I) which is -CO-OH and the acid chloride reagent are mixed and contacte...

Embodiment 3

[0139] Embodiment 3 --- the preparation of compound 3

[0140] Carry out according to the reaction process shown in following formula IV,

[0141]

[0142] This embodiment is used to prepare compound 3 shown in Table 1, as recorded in Table 1, in the above-mentioned formula (IX)-formula (I), R 1 =CH 3 , R 2 =CH 3 , R 3 = F, R 4 = H, R 5 = Cl, R 6 = H, R 7 = H, R 8 = H, R 9 =CH 3 , R 10 =CO-OC 2 h 5 .

[0143] In order to be more intuitive, the above formula IV is specifically rewritten as the process of preparing compound 3, as shown in the following formula V.

[0144]

[0145] The specific process includes:

[0146] 1) Preparation of Compound IV

[0147] Dissolve 0.206 mol of the compound represented by formula (IX) in 200 mL of ethanol, lower it to 0° C., add dropwise 0.25 mol of an aqueous solution of hydroxylamine hydrochloride under stirring, and then rise to room temperature and stir to react. After 2 hours, TLC detected that the reaction was com...

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Abstract

The invention relates to the field of pesticides, particularly to a thiotriazinone isoxazoline compound, a preparation method and application thereof, a herbicide containing the thiotriazinone isoxazoline compound, and a protoporphyrinogen oxidase inhibitor, wherein the thiotriazinone-containing isoxazoline compound has a structure represented by a formula (I), and R<1> and R<2> are respectively and independently selected from H, -NH2, C1-C6 alkyl or C1-C6 halogenated alkyl and the like. The thiotriazinone isoxazoline compound provided by the invention can efficiently inhibit the activity of plant protoporphyrinogen oxidase, and has good herbicidal activity and crop safety.

Description

technical field [0001] The present invention relates to the field of pesticides, in particular to a thiotriazinone-isoxazoline compound, a preparation method and application thereof, and a compound containing the thiotriazinone-isoxazoline compound and a protoporphyrinogen oxidase inhibitor and herbicides. Background technique [0002] The use of herbicides can be traced back to around the 1960s. After more than half a century of research, many types of herbicides have been developed, and these herbicides inhibit the growth of weeds through various mechanisms. . Some of these herbicides target one or more enzymes in weeds, inhibiting the normal function of these enzymes, so that weeds cannot grow normally. With the widespread use and long-term use of these herbicides, weeds have increasingly developed resistance to these enzyme-inhibiting herbicides, showing a trend that is difficult to be suppressed. Discovering compounds with novel structures and higher enzyme inhibitor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/10C07D413/14A01N43/80A01P13/00
CPCC07D413/10C07D413/14A01N43/80
Inventor 席真张瑞波王大伟于淑一
Owner NANKAI UNIV
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