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Dioxoquinoxaline formamidourea with plant growth regulating activity, preparation method and application thereof

A quinoxaline carboxamide urea, plant growth regulation technology, applied in directions such as plant growth regulators, plant growth regulators, botanical equipment and methods, and can solve problems such as no mention of compounds

Inactive Publication Date: 2013-01-23
HUAZHONG AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Diazoxyquinoxaline derivatives have antibacterial, insecticidal, anticancer and animal growth-promoting activities, and relevant documents have been reported abroad (Kamelia M, Amin, Magda M.F.Ismail, New quinoxaline1, 4-di-N -oxides.Part 1: Hypoxia-selective cytotoxins and anticancer agents derived from quinoxaline 1,4-di-N-oxides[J], Bioorganic & Medicinal Chemistry, 2006, 14:6917-23; Sainz Montoya Y, Martinez ME, Crespo - FJ Ortega, Lopez M A.A New quinoxaline 1, 4-di-N-oxides for treatment of tuberculosis [J]. Arzneimittel-Forschung, 1999, 49(1): 55-59; Broz J, Sevcik B, Hebky J, Cyadox-a new Czechoslovak animal growth regulator[J]. Agrochemia, 1980, 20: 339-324; Antonio Carta, Mario Loriga, Giuseppe Paglietti, Synthesis, anti-mycobacterial, anti-trichomonas and anti-candida in vitro activities of 2- substituted-6,7-difluoro-3-methyl-quinoxaline 1,4-dioxides[J], European Journal of Medicinal Chemistry, 2004,39(2):195-203), these documents do not mention the compound prepared by the present invention

Method used

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  • Dioxoquinoxaline formamidourea with plant growth regulating activity, preparation method and application thereof
  • Dioxoquinoxaline formamidourea with plant growth regulating activity, preparation method and application thereof
  • Dioxoquinoxaline formamidourea with plant growth regulating activity, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] Embodiment 1: the preparation of N-diazaoxyquinoxaline carboxamido-N'-phenylurea

[0070] The preparation of intermediate compound diazoxyquinoxaline formic acid ethyl ester:

[0071] Take 10g of benzofurazan (about 0.074mol) and add it into a 250ml three-neck flask equipped with a mechanical stirrer and a reflux condenser, and add 20mL of triethylamine in a water bath at 25°C. While stirring, 17 mL of ethyl acetoacetate was added dropwise, and the benzofurazan gradually dissolved as the dropwise addition progressed, and finally the solution turned black red, and the stirring was stopped. After standing in a water bath at 25°C for 48 hours, a large amount of orange-yellow solids precipitated. Suction filtration, washing the filter cake with water to obtain a yellow needle-like solid, which was recrystallized from anhydrous methanol to obtain 9 g of the intermediate product ethyl diazoxyquinoxaline carboxylate, the yield was 50%, m.p.122-124°C.

[0072] The preparation...

Embodiment 2

[0082] Embodiment 2: Plant growth regulation activity experiment 1

[0083] Divide the barnyardgrass that grows uniformly into multiple groups, with four bowls in each group. Treat barnyard grass with one leaf and one heart, use the emulsion blank (Tween-80) (see Table 2 for content) as a contrast, and other groups use the above-mentioned compound of the present invention to prepare different concentration emulsions (see Table 2 for content) respectively, and each bowl of 10mL is used for Plant stem and leaf treatment. Set up 3 parallel samples, measure the relevant indexes about plant growth 10 days after plant application, and calculate the inhibition rate of plant root and stem length. The test results are shown in Table 2.

[0084] Table 2 The compounds synthesized by the present invention regulate the growth of monocot weed barnyardgrass

[0085]

[0086]

[0087] Table 2 (continued 1) The compounds synthesized by the present invention regulate the growth of mono...

Embodiment 3

[0096] Embodiment 3: Plant growth regulation activity test 2

[0097] The plant growth regulation activity experiment was carried out with amaranth and rapeseed as objects, and the test method was as in Example 2. The experimental results are shown in Table 3.

[0098] Table 3 The compounds synthesized by the present invention regulate the growth of dicotyledons amaranth and rapeseed

[0099]

[0100]

[0101] Table 3 (continued 1) The synthetic compound of the present invention is to the growth regulation situation of dicotyledon amaranth and rapeseed

[0102]

[0103] Table 3 (continued 2) The new compound synthesized by the present invention is to the growth regulation situation of dicotyledon amaranth and rapeseed

[0104]

[0105] Table 3 (continued 3) The new compound synthesized by the present invention is to the growth regulation situation of dicotyledon amaranth and rapeseed

[0106]

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Abstract

The invention specifically relates to a compound with a plant growth regulating activity, a preparation and an application thereof. The compound contains quinoxaline formamidourea as shown in the general formula 1, in which R is an alkyl, phenyl or substituted phenyl group. The substituted phenyl group can be a substituted or multi-substituted phenyl group, wherein R' on the multi-substituted phenyl group can be the same and can also be different; the position of R' group on the phenyl group is any one or more positions selected from 2, 3, 4, 5 and 6- positions, and the substituent group is methyl, nitryl, alkoxide, halogen atom or fluoroform. The preparation method comprises the following steps of: performing two-step reaction on benzofurazan used as a raw material to obtain a quinoxaline formylhydrazine intermediate; performing a reaction between amine and solid phosgene to synthesize a rotaxane formation intermediate, and performing a reaction between the quinoxaline formylhydrazine intermediate and the rotaxane formation intermediate to obtain the compound as shown in the general formula 1. The invention also discloses a preparation of the intermediates. The compound as shown in the general formula 1 has an obvious effect of regulating the growth of monocotyledons and dicotyledons, and can be used as a growth regulator for monocotyledon and dicotyledon weeds.

Description

technical field [0001] The invention belongs to the technical field of compound preparation, and specifically relates to a diazoxyquinoxaline carboxamide urea compound with plant growth regulating activity, its preparation method and application. Background technique [0002] Diazoxyquinoxaline derivatives have antibacterial, insecticidal, anticancer and animal growth-promoting activities, and relevant documents have been reported abroad (Kamelia M, Amin, Magda M.F.Ismail, New quinoxaline1, 4-di-N -oxides.Part 1: Hypoxia-selective cytotoxins and anticancer agents derived from quinoxaline 1,4-di-N-oxides[J], Bioorganic & Medicinal Chemistry, 2006, 14:6917-23; Sainz Montoya Y, Martinez ME, Crespo - FJ Ortega, Lopez M A.A New quinoxaline 1, 4-di-N-oxides for treatment of tuberculosis [J]. Arzneimittel-Forschung, 1999, 49(1): 55-59; Broz J, Sevcik B, Hebky J, Cyadox-a new Czechoslovak animal growth regulator[J]. Agrochemia, 1980, 20: 339-324; Antonio Carta, Mario Loriga, Giusep...

Claims

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Application Information

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IPC IPC(8): C07D241/52A01N47/34A01P21/00
Inventor 马敬中杜春燕马中华朱凯英江洪
Owner HUAZHONG AGRICULTURAL UNIVERSITY
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