CN102146068A - 3-benzoyl-4-hydroxycoumarin derivatives and analogues thereof and application thereof in weeding aspect - Google Patents
3-benzoyl-4-hydroxycoumarin derivatives and analogues thereof and application thereof in weeding aspect Download PDFInfo
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- CN102146068A CN102146068A CN2011100226818A CN201110022681A CN102146068A CN 102146068 A CN102146068 A CN 102146068A CN 2011100226818 A CN2011100226818 A CN 2011100226818A CN 201110022681 A CN201110022681 A CN 201110022681A CN 102146068 A CN102146068 A CN 102146068A
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Abstract
The invention relates to 3-benzoyl-4-hydroxycoumarin derivatives and analogues thereof and application thereof in the agricultural weed control aspect. The compounds have the structural general formula (I). R1 and R2 respectively represent one, two or three of hydrogen, halogen, nitryl, hydroxyl, methyl, ethyl, trifluoromethyl, methoxyl, ethyoxyl, trifluoromethoxy and methanesulfonic acid group; R3 represents hydrogen; R4 represents methoxyl or does not represent any atom or group; X represents O; Y represents O; Z represents O and N; and W represents O. The compounds are designed by taking a natural product coumarin as a template, and have structures similar to those of triketone herbicides. Through activity screening, the compounds have good weeding activity and are herbicides with novel structures and wide application prospect.
Description
Technical field
The present invention relates to a kind of 3-benzoyl-4 hydroxy coumarin derivative and similar compound thereof and the application aspect agricultural weed control.
Technical background
Tonka bean camphor is the secondary metabolite that a class extensively exists.Though simple in structure, have multiple biological activity, comprise weeding activity.Trione compounds is HPPD enzyme (p-Hydroxyphenylpyruvate dioxygenase) inhibitor, the three ketones commodity weedicide of Syngenta Co.,Ltd's exploitation comprises sulphur humulone (sulcotrione) and mesotrione (mesotrione), and the characteristic feature of this weedicide has whitening action to weeds exactly.
The present invention utilizes active synergetic principle, and the 3-benzoyl-4 hydroxy coumarin derivative that has the three ketones structure has been synthesized in design.Up to the present, have only a patent (WO8804652) to relate to the application of a compound [3-(2,4 dichloro benzene formyl radical)-4 hydroxy coumarin] aspect weeding in this compounds.The present invention relates to a large amount of these compounds except that 3-(2,4 dichloro benzene formyl radical)-4 hydroxy coumarin first in the application aspect the weeding.
Summary of the invention
The object of the present invention is to provide a kind of 3-benzoyl-4 hydroxy coumarin derivative and analogue and the application aspect weeding.
The general structure of 3-benzoyl provided by the invention-4 hydroxy coumarin derivative and analogue thereof is:
Wherein: R
1And R
2Represent hydrogen, halogen, nitro, alkyl, hydroxyl, alkoxyl group, sulfydryl, alkane sulfydryl and alkyl sulfonic acid base one or more; R
3Represent hydrogen, alkyl and alkoxyl group one of them; R
4Represent hydrogen, alkyl and alkoxyl group, or do not represent any atom and group.
X, Y, Z, W represent O, S, NH and N one of them.
Preferentially, R
1And R
2Represent alkyl, the alkoxyl group of C1～C5, the alkane sulfydryl of C1～C3, the C1～C3 alkyl sulfonic acid base of hydrogen, halogen, nitro, hydroxyl, sulfydryl, C1～C5; R3 represents the alkyl of hydrogen, C1～C5 and the alkoxyl group of C1～C5; R4 represents hydrogen, C1～C5 alkyl and C1～C5 alkoxyl group, or does not represent any atom and group.
Again preferentially, R
1And R
2Represent wherein one to three of hydrogen, halogen, nitro, hydroxyl, methyl, ethyl, trifluoromethyl, methoxyl group, oxyethyl group, trifluoromethoxy and methylsulfonic acid base respectively; R
3Represent hydrogen; R
4Representation methoxy, or do not represent any atom and group; X represents O; Y represents O; Z represents O and N; W represents O.
Compound that the present invention relates to and acceptable salt thereof are used as weedicide on agricultural.
The compound that the present invention relates to and on agricultural acceptable salt can also mix as pesticide composition with other compositions as effective constituent, be used as weedicide.
The synthetic method of the compound that the present invention relates to following (dividing for 3 steps):
1) o-hydroxyacetophenone 1 of Qu Daiing reacts 4 hydroxy coumarin 2 that 1～6hs obtain replace in 70～120 times ℃ with diethyl carbonate in toluene under the situation that alkali exists.
2) 4 hydroxy coumarin 2 that replaces obtains intermediate 3 with the Benzoyl chloride esterification that replaces earlier, without isolation identification, directly resets the 3-benzoyl-4 hydroxy coumarin 4 that obtains replacing in methylene dichloride under the catalysis of KCN
3) 3-benzoyl-4 hydroxy coumarin 4 obtains 4 similar compound 5 with the alkyl azanol reaction in pyridine.
The present invention is that stencil design forms with the natural product tonka bean camphor, has the similar structure of three ketones weedicide simultaneously.
Screening active ingredients finds that this compounds has good weeding activity, is a class formation novelty, the weedicide that has a extensive future.
Embodiment
This aspect is described in detail as follows with reference to embodiment:
Embodiment 1
Add 2.97g NaH in the 50mL toluene, be added dropwise to the toluene solution (3.00g is in 50mL toluene) of 2-hydroxy acetophenone under the ice bath, add the 3.0mL diethyl carbonate afterwards.Afterwards, react 3h down at 120 ℃.Ice bath adds 80mL water down, separatory, and water is separated out solid with the acidifying of 1mol/L HCl solution.Suction filtration goes out solid, and infrared drying gets beige solid 4 hydroxy coumarin 2.60g, productive rate 72.9%.Related data is as follows: fusing point: 207～209 ℃,
1HNMR (400MHz, d
6-DMSO) δ: 5.63 (s, 1H, CH), 7.36-7.39 (m, 2H, Ar-H), 7.67 (dd,
3J=7.2Hz,
4J=1.1Hz), 7.84 (dd,
3J=7.8Hz, 4J=1.1Hz, Ar-H), 12.56 (bs, 1H ,-OH);
13CNMR (100MHz, d
6-DMSO) δ: 91.0,115.7,116.3,123.1,123.9,132.7,153.5,161.8,165.5.
Dissolving 0.6g Benzoyl chloride in the 30mL methylene dichloride, disposable adding 4 hydroxy coumarin 0.63g drips the dichloromethane solution (the 0.8mL triethylamine is dissolved in the 10mL methylene dichloride) of triethylamine then.Stirring at room 2h.Afterwards, twice usefulness 30mL 1mol/L HCl solution washing reaction system.MgSO
4Drying is spin-dried for solvent, obtains the 0.98g solid, dissolves this solid with fresh methylene dichloride again, adds 0.10g KCN, 0.1g 18-hat-6 and 0.8mL triethylamine.Stirring at room 48h uses FeSO afterwards
41mol/L HCl solution washing (2.0g 30mL), uses the saturated common salt water washing, MgSO again
4Dry.After being spin-dried for, use column chromatography, eluent is methylene dichloride/acetate=100/1 (v/v).Obtain 0.58g light yellow solid 3-benzoyl-4 hydroxy coumarin I-1, yield 55.9%.The I-1 related data is as follows: fusing point 145-146 ℃;
1HNMR (400MHz, CDCl
3) δ: 7.34-741 (m, 2H, Ar-H), 7.49 (t,
3J=7.4Hz 1H, Ar-H), 7.60 (t,
3J=7.3Hz, Ar-H), 7.72-7.76 (m, 3H, Ar-H), 8.14 (d,
3J=7.8Hz, 1H, Ar-H);
13C NMR (100MHz, CDCl
3) δ: 100.7,115.2,117.1,124.5,125.6,127.9 (2C), 128.4 (2C), 132.6,136.2,137.8,155.2,159.5,178.1,200.9.
Embodiment 2
1.0g 3-(2-chlorobenzene formacyl)-4 hydroxy coumarin I-2 is dissolved in the 20mL pyridine; add the 0.41g methoxy amine hydrochlorate; stirring at room 30h; afterwards, distill out pyridine, remaining solid dissolves with methylene dichloride; and use column chromatography purification; eluent is ethyl acetate/petroleum ether=3/10 (v/v), gets yellow solid I-30.56g, yield 51.1%.
The related data of I-3 is as follows: 164～166 ℃ of fusing points;
1H NMR (400MHz, CDCl
3) δ: 3.99 (s, 3H, CH
3), 7.19 (dd, 3J=6.6Hz,
4J=2.3Hz, 1H, Ar-H), 7.25-7.27 (m, 1H, Ar-H), 7.30-7.37 (m, 3H, Ar-H), 7.45 (dd,
3J=7.0Hz,
4J=1.7Hz, Ar-H) 7.58 (t,
3J=8.2Hz, 1H, Ar-H), 8.02 (d,
3J=7.9Hz, 1H, Ar-H), 13.98 (br, 1H, OH);
13C NMR (100MHz, CDCl
3) δ: 63.3,97.2,115.6,116.6,124.1,124.4,126.4,128.2,129.1,129.9,131.3,132.3,133.5,153.3.157.5,159.3,167.4;
Synthesized Compound I-2, I-4～I-21 according to the synthetic operation similar to embodiment 1, its substituting group classification and physical properties are listed in the table 1.In the compound in the table 1, X, Y, Z and W are Sauerstoffatom, R
3=R
4=H.
Table 1
Embodiment 3
Rape (Brassica campestris) Plating: the filter paper of completing a diameter 5.6cm in the culture dish of diameter 6cm, add the certain density test compound solution of 2mL, the blank of adding distil water is set, 15 of the Semen Brassicae campestris grains of sowing seed soaking 4～6h, under 30 ± 1 ℃, black box has been cultivated and has been measured radicle length behind the 66h. the growth-inhibiting of rape radicle is come the weeding activity of detection compound by compound under the dark condition.All compounds are listed in the table 2 the inhibition activity of rape.
Table 2
Claims (6)
1. a 3-benzoyl-4 hydroxy coumarin derivative and similar compound thereof is characterized in that its general structure is:
Wherein, R
1And R
2Represent hydrogen, halogen, nitro, alkyl, hydroxyl, alkoxyl group, sulfydryl, alkane sulfydryl and alkyl sulfonic acid base one or more; R
3Represent hydrogen, alkyl and alkoxyl group one of them; R
4Represent hydrogen, alkyl and alkoxyl group, or do not represent any atom and group;
X, Y, Z, W represent O, S, NH and N one of them.
2. compound according to claim 1 is characterized in that: R
1And R
2Represent alkyl, the alkoxyl group of C1～C5, the alkane sulfydryl of C1～C3, the C1～C3 alkyl sulfonic acid base of hydrogen, halogen, nitro, hydroxyl, sulfydryl, C1～C5; R
3Represent the alkyl of hydrogen, C1～C5 and the alkoxyl group of C1～C5; R
4Represent hydrogen, C1～C5 alkyl and C1～C5 alkoxyl group, or do not represent any atom and group.
3. compound according to claim 1 is characterized in that: R
1And R
2Represent wherein one to three of hydrogen, halogen, nitro, hydroxyl, methyl, ethyl, trifluoromethyl, methoxyl group, oxyethyl group, trifluoromethoxy and methylsulfonic acid base respectively; R
3Represent hydrogen; R
4Representation methoxy, or do not represent any atom and group; X represents O; Y represents O; Z represents O and N; W represents O.
4. the synthetic method of the described compound of claim 3 is characterized in that comprising the steps:
1) o-hydroxyacetophenone 1 of Qu Daiing reacts 4 hydroxy coumarin 2 that 1～6hs obtain replace in 70～120 times ℃ with diethyl carbonate in toluene under the situation that alkali exists;
2) 4 hydroxy coumarin 2 that replaces obtains intermediate 3 with the Benzoyl chloride esterification that replaces earlier, without isolation identification, directly resets the 3-benzoyl-4 hydroxy coumarin 4 that obtains replacing in methylene dichloride under the catalysis of KCN
3) 3-benzoyl-4 hydroxy coumarin 4 obtains 4 similar compound 5 with the alkyl azanol reaction in pyridine;
Each described compound of claim 1～3 and acceptable salt thereof on agricultural as herbicide applications.
6. a pesticide composition is characterized in that containing each described compound of claim 1～3, perhaps contains its acceptable salt on agricultural.
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104447614A (en) * | 2015-01-14 | 2015-03-25 | 南开大学 | 4-hydroxy-3-benzoyl-1-alkyl-2, 1-benzothiazine-2, 2-dioxide derivative and application |
| CN104592183A (en) * | 2015-01-15 | 2015-05-06 | 青岛农业大学 | N-acyl-N-m-fluorobenzyl-8-aminocoumarin compounds and preparation method and weeding application thereof |
| CN105111176A (en) * | 2015-10-16 | 2015-12-02 | 南开大学 | 3-phenoxyacetyl-4-hydroxycoumarin derivative, synthetic method and application |
| CN108727346A (en) * | 2017-04-14 | 2018-11-02 | 河北农业大学 | A kind of preparation method and purposes of isocoumarin pyridinium salt |
| CN110452208A (en) * | 2019-09-03 | 2019-11-15 | 皇甫谧(宁波)科技发展有限公司 | A kind of preparation method of high yield high-purity 4 hydroxy coumarin |
| CN110615784A (en) * | 2019-10-25 | 2019-12-27 | 南开大学 | Synthesis and application of lactone analogue with flavone skeleton |
| WO2020023368A1 (en) * | 2018-07-23 | 2020-01-30 | Hamyard Associates LLC | Pogostone derivatives and methods of using the same |
| CN111072615A (en) * | 2019-11-08 | 2020-04-28 | 聊城大学 | Synthesis of 3- (1-aminoethylidene) -6-methyl pyran-2, 4-dione derivative and application thereof as herbicide |
| CN112806361A (en) * | 2019-11-18 | 2021-05-18 | 党永富 | Carbon adsorption 4-hydroxycoumarin herbicide safety additive and application thereof in treatment of herbicide side effects |
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| CN104447614A (en) * | 2015-01-14 | 2015-03-25 | 南开大学 | 4-hydroxy-3-benzoyl-1-alkyl-2, 1-benzothiazine-2, 2-dioxide derivative and application |
| CN104592183A (en) * | 2015-01-15 | 2015-05-06 | 青岛农业大学 | N-acyl-N-m-fluorobenzyl-8-aminocoumarin compounds and preparation method and weeding application thereof |
| CN105111176A (en) * | 2015-10-16 | 2015-12-02 | 南开大学 | 3-phenoxyacetyl-4-hydroxycoumarin derivative, synthetic method and application |
| CN108727346A (en) * | 2017-04-14 | 2018-11-02 | 河北农业大学 | A kind of preparation method and purposes of isocoumarin pyridinium salt |
| WO2020023368A1 (en) * | 2018-07-23 | 2020-01-30 | Hamyard Associates LLC | Pogostone derivatives and methods of using the same |
| CN110452208A (en) * | 2019-09-03 | 2019-11-15 | 皇甫谧(宁波)科技发展有限公司 | A kind of preparation method of high yield high-purity 4 hydroxy coumarin |
| CN110615784A (en) * | 2019-10-25 | 2019-12-27 | 南开大学 | Synthesis and application of lactone analogue with flavone skeleton |
| CN110615784B (en) * | 2019-10-25 | 2022-10-25 | 南开大学 | Synthesis and application of lactone analogue with flavone skeleton |
| CN111072615A (en) * | 2019-11-08 | 2020-04-28 | 聊城大学 | Synthesis of 3- (1-aminoethylidene) -6-methyl pyran-2, 4-dione derivative and application thereof as herbicide |
| CN112806361A (en) * | 2019-11-18 | 2021-05-18 | 党永富 | Carbon adsorption 4-hydroxycoumarin herbicide safety additive and application thereof in treatment of herbicide side effects |
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Application publication date: 20110810 |