CN105766964A - Agricultural herbicide and preparation method thereof - Google Patents
Agricultural herbicide and preparation method thereof Download PDFInfo
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- CN105766964A CN105766964A CN201610257800.0A CN201610257800A CN105766964A CN 105766964 A CN105766964 A CN 105766964A CN 201610257800 A CN201610257800 A CN 201610257800A CN 105766964 A CN105766964 A CN 105766964A
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/92—Naphthofurans; Hydrogenated naphthofurans
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
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- General Health & Medical Sciences (AREA)
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Abstract
The invention discloses an agricultural herbicide and a preparation method thereof. The herbicide contains isoproturon and a compound which is obtained through extraction separation from semen cuscutae and novel in structure, and the compound is reported for the first time. The invention further provides a preparation method of the compound. The preparation method comprises the following steps: crushing dried mature seeds of the semen cuscutae, performing hot reflux extraction with ethanol, performing liquid-liquid extraction with a solvent, performing trash extraction with macroporous resin on an ethyl acetate extract, performing normal phase silica gel separation, performing antiphase silica gel separation and the like. Experiment results indicate that the herbicide provided by the invention can selectively restrain the growth of annual gramineous weeds including beckmannia syzigachne in wheat fields, alopecurus japonicus and the like, and the growth of broadleaf weeds including stellaria media, malachium aquaticum and the like.
Description
Technical field
The invention belongs to agriculture field, be specifically related to a kind of agricultural herbicide and preparation method thereof.
Background technology
Semen Tritici aestivi, rice, the most important several cereal crops of Semen Maydis Deng Shi China, the height of grain yield is directly connected to national food security, social stability and harmony.For the variety of crops that this north of Semen Tritici aestivi is main, the unordered growth of the malignant weeds such as hard grass, amur foxtail, Alopecurus, Beckmannia syzigachne (Steud.) Fern has a strong impact on wheat yield.Wherein in recent years Alopecurus and Beckmannia syzigachne (Steud.) Fern cause harm area and severity strengthens year by year, indivedual field wheat yields in minority area lose up to 2～3 one-tenth, the most serious field forms farmland running to weeds, the harm solving both weeds is extremely urgent, becomes Wheat Diseases And Insect Pests and prevents one of topmost problem in field.
At present, the medicament applied for Semen Tritici aestivi grassy weed mainly has clodinafop-propargyl, fenoxapropPethyl, chlortoluron, isoproturon and isoproturon chlortoluron etc., facts have proved through production application, wheatland is firmly careless, the common amur foxtail preventive effect of these medicaments is better, the preventive effect of Alopecurus and Beckmannia syzigachne (Steud.) Fern is only had 30-40% poor.It seems that from the herbicide kind listed at present, but without one, wheatland grass, Alopecurus had single dose or the built agent product of excellent preventive effect up to now, owing to lacking this type of herbicide, cause that different herbicides can only be carried out arbitrarily collocation according to experience when field weeding and use with by Mai Nong, lack science, preventive effect is unstable, often occurs poisoning to cause wheat yield.
Summary of the invention
It is an object of the invention to provide a kind of agricultural herbicide, this herbicide can optionally suppress the growth of the annual gramineous weeds such as wheatland grass, Alopecurus and the broad leaved weed such as Herba stellariae mediae, cattle Herba stellariae mediae.
Above-mentioned purpose is achieved by the techniques below scheme:
A kind of agricultural herbicide, containing the compound (I) shown in isoproturon and following structure,
Further, the ratio of compound (I) described in described agriculture herbicide and the amount of substance of isoproturon is 3～5:1.
The preparation method of described compound (I), comprise following operating procedure: the dry mature seed of Semen Cuscutae is pulverized by (a), extract with 80～90% alcohol heat reflux, united extraction liquid, it is concentrated into without alcohol taste, successively with petroleum ether, ethyl acetate and water saturated n-butanol extraction, respectively obtain petroleum ether extract, acetic acid ethyl ester extract and n-butyl alcohol extract；B acetic acid ethyl ester extract macroporous resin remove impurity in () step (a), first with 6 column volumes of 10% ethanol elution, then with 10 column volumes of 75% ethanol elution, collects 75% ethanol elution, concentrating under reduced pressure obtains 75% ethanol elution thing extractum；In (c) step (b) 75% ethanol elution extractum with purification on normal-phase silica gel separate, successively with volume ratio be 80:1,55:1,30:1,15:1 and 1:1 methylene chloride-methanol gradient elution obtain 5 components；D in () step (c), component 4 separates further by purification on normal-phase silica gel, successively with volume ratio be 20:1,15:1 and 10:1 methylene chloride-methanol gradient elution obtain 3 components；E reverse phase silica gel that in () step (d), component 2 is bonded by octadecylsilane separates, with the methanol aqueous solution isocratic elution that concentration expressed in percentage by volume is 75%, collecting 8～10 column volume eluents, eluent concentrating under reduced pressure obtains compound (I).
Further, described macroporous resin is AB-8 type macroporous adsorbent resin.
Further, described alcohol heat reflux extracts the concentration of alcohol adopted is 85%.
The application in preparation agricultural herbicide of the described compound (I).
Beneficial effects of the present invention:
Herbicide provided by the invention can optionally suppress the growth of the annual gramineous weeds such as wheatland grass, Alopecurus and the broad leaved weed such as Herba stellariae mediae, cattle Herba stellariae mediae.
Detailed description of the invention
Further illustrate the essentiality content of the present invention below in conjunction with embodiment, but do not limit scope with this.Although the present invention being explained in detail with reference to preferred embodiment, it will be understood by those within the art that, it is possible to technical scheme is modified or equivalent replacement, without deviating from the spirit and scope of technical solution of the present invention.
Embodiment 1: compound (I) separates preparation and structural identification
Reagent source: ethanol, petroleum ether, ethyl acetate, n-butyl alcohol, dichloromethane are analytical pure, purchased from Shanghai Ling Feng chemical reagent company limited, methanol, analytical pure, purchased from Jiangsu Han Bang chemical reagent company limited.
Preparation method: the dry mature seed (1kg) of Semen Cuscutae is pulverized by (a), extract with 85% alcohol heat reflux, united extraction liquid, it is concentrated into without alcohol taste, successively with petroleum ether, ethyl acetate and water saturated n-butanol extraction, respectively obtain petroleum ether extract, acetic acid ethyl ester extract and n-butyl alcohol extract；Acetic acid ethyl ester extract AB-8 type macroporous resin remove impurity in (b) step (a), first with 6 column volumes of 10% ethanol elution, again with 10 column volumes of 75% ethanol elution, collecting 75% ethanol elution, concentrating under reduced pressure obtains 75% ethanol elution thing extractum；C in () step (b), 75% ethanol elution extractum purification on normal-phase silica gel separates, obtain 5 components with the methylene chloride-methanol gradient elution that volume ratio is 80:1 (8 column volumes), 55:1 (8 column volumes), 30:1 (6 column volumes), 15:1 (8 column volumes) and 1:1 (5 column volumes) successively；D in () step (c), component 4 separates further by purification on normal-phase silica gel, obtain 3 components with the methylene chloride-methanol gradient elution that volume ratio is 20:1 (8 column volumes), 15:1 (10 column volumes) and 10:1 (6 column volumes) successively；E reverse phase silica gel that in () step (d), component 2 is bonded by octadecylsilane separates, with the methanol aqueous solution isocratic elution that concentration expressed in percentage by volume is 75%, collecting 8～10 column volume eluents, eluent concentrating under reduced pressure obtains compound (I) (2.3g).
Structural identification: white powder.HR-ESI-MS shows [M+H]+For m/z305.1346, can obtain molecular formula in conjunction with nuclear-magnetism feature is C17H20O5, degree of unsaturation is 8.Hydrogen nuclear magnetic resonance modal data δH(ppm, CDCl3null，500MHz): H-2 (5.84，t，J=3.9Hz)，H-3a(2.69，dd，J=11.8，12.3Hz)，H-3b(2.63，dd，J=11.8，6.1Hz)，H-5(2.36，d，J=10.3Hz)，H-6(4.12，dd，J=10.3，11.2Hz)，H-7(2.52，dt，J=11.2，3.3Hz)，H-8a(2.08，m)，H-8b(1.61，ddt，J=12.3，3.1，13.2Hz)，H-9a(1.38，dt，J=4.1，13.2Hz)，H-9b(2.11，dt，J=13.2，3.1Hz)，H-13a(6.12，d，J=3.3Hz)，H-13b(5.42，d，J=3.3Hz)，H-14(0.95，s)，H-15a(5.05，s)，H-15b(5.02，s)，2-OAc(2.06，s)；Carbon-13 nmr spectra data δC(ppm, CDCl3, 125MHz): 207.4 (C, 1-C), 85.3 (CH, 2-C), 33.1 (CH2, 3-C), 137.5 (C, 4-C), 50.4 (CH, 5-C), 78.7 (CH, 6-C), 49.8 (CH, 7-C), 20.6 (CH2, 8-C), 35.6 (CH2, 9-C), 46.5 (C, 10-C), 139.7 (C, 11-C), 170.5 (C, 12-C), 117.2 (CH2, 13-C), 13.4 (CH3, 14-C), 116.8 (CH2, 15-C), 170.7 (C, 2-OAc), 22.2 (CH3, 2-OAc).1716cm in infrared spectrum-1236nm absorption band in absorption band and UV spectrum shows that this compound contains gamma lactone structure, further and by analysis13δ in C-NMR spectrumC78.7, the carbon signal of 49.8,139.7,170.5,117.2 is known exists the outer methylene gamma lactone structure of ring.13C-NMR, DEPT and hsqc spectrum show 17 carbon signals, including two methyl (acetonyl), five methylene (two alkene carbon), four methines (two company's oxygen carbon), and six quaternary carbons (two alkene carbon and three carbonyl carbon).In conjunction with insatiable hunger sum, function above structure shows that this compound is tricyclic structure.1H-NMR spectrum shows two methyl proton signal δ in conjunction with hsqc spectrumH0.95 (3H, s), 2.06 (3H, s), two opposite end olefinic proton signals δH6.12 (1H, d, J=3.3Hz) and 5.42 (1H, d, J=3.3Hz), 5.05 (1H, s) with 5.02 (1H, s), two even oxygen methine proton signal δH5.84 (1H, t, J=3.9Hz), 4.12 (1H, dd, J=10.3,11.2Hz).13δ in C-NMR spectrumC137.5 with 116.8 coherent signals and1δ in H-NMR spectrumH5.05 (1H, s) (1H, s) coherent signal, H in composing in conjunction with HMBC with 5.022-15 imply the presence of the outer methylene of an other ring with the coherent signal of C-4.Additionally,13δ in C-NMR spectrumC170.7 with 22.2 coherent signals and1δ in H-NMR spectrumH2.06 (1H, s) coherent signal, H-2 and carbonyl carbon δ in composing in conjunction with HMBCC170.7 coherent signal show structure exists acetoxyl group.1H-1There is H-2/H in HCOSY spectrum2-3、H-5/H-6/H-7/H2-8/H2-9 coherent signals, and H-2 and C-1 and the C-3, the H that show in HMBC spectrum2-3 with C-1, C-2, C-4 and C-5, H-5 and C-6 and C-10, H-6 and C-7, C-8, C-11 and C-12, H-7 and C-6, C-11, C-12 and C-13, H2-13 with C-7 and C-12, H3-14 and C-10, H-OMeWith C-2 coherent signal, the connected mode of this compound can be built, and above-mentioned spectral data shows that this compound is eudesmane, and there is the outer methylene gamma lactone structure of ring, acetoxyl group is connected to C-2 position, C-2 in this compound, C-5, C-6, C-7 and C-10 are chiral carbon, confirm relative configuration by NOESY test with H-H coupling constant.In NOESY spectrum there is H-6/H-8a, H-6/H in display3-14 and H-8a/H3-14 coherent signals, show that these hydrogen are in the same side, another H-5/H-9a coherent signal shows that these hydrogen are in the same side, these coherent signals are consistent to the result of relevant coupling constant, and also indicating that the trans connection of A/B and B/C ring, therefore above coherent signal may indicate that the C-2 of this compound, C-5, C-6, C-7 and C-10 are configured as 2R, 5R, 6S, 7S and 10R.Comprehensive hydrogen spectrum, carbon spectrum, HMBC spectrum and NOESY spectrum, and document is about correlation type nuclear magnetic data, can substantially determine that this compound is as follows, spatial configuration is determined by ECD test further, and theoretical value is basically identical with experiment value.Carbon atoms numbered is as follows:
Embodiment 2: the preparation of herbicide and herbicidal effect
Taking appropriate solvent DMSO isoproturon and compound (I) to be dissolved, then dilute with tap water, the molar concentration of isoproturon is 80 μ g/ml, and the molar concentration of compound (I) is 320 μ g/ml.Molar concentration is isoproturon molar concentration 3～5 times of compound (I).
Using method a: week sprays twice.
With to wheatland grass, Alopecurus, Herba stellariae mediae, cattle Herba stellariae mediae suppression ratio for inspection target, it is respectively provided with test group one and test group two, test group one sprays herbicide provided by the invention, contains only the isoproturon identical with test group one concentration in the herbicide of test group two.Duration of trial is 1 month.Result is shown in following table.
| Wheatland grass suppression ratio | Alopecurus suppression ratio | Herba stellariae mediae suppression ratio | Cattle Herba stellariae mediae suppression ratio | |
| Test group one | 97% | 98% | 95% | 96% |
| Test group two | 47% | 39% | 44% | 43% |
Result shows, in the herbicide of the present invention, herbicidal effect has been played very important effect by compound (I), illustrates that herbicide provided by the invention can optionally suppress the growth of the annual gramineous weeds such as wheatland grass, Alopecurus and the broad leaved weed such as Herba stellariae mediae, cattle Herba stellariae mediae.
The effect of above-described embodiment indicates that the essentiality content of the present invention, but does not limit protection scope of the present invention with this.It will be understood by those within the art that, it is possible to technical scheme is modified or equivalent replacement, without deviating from essence and the protection domain of technical solution of the present invention.
Claims (6)
1. an agriculture herbicide, it is characterised in that: containing the compound (I) shown in isoproturon and following structure,
2. agricultural herbicide according to claim 1, it is characterised in that: the ratio of described compound (I) and the amount of substance of isoproturon is 3～5:1.
3. the preparation method of the compound (I) described in claim 1 or 2, it is characterized in that comprising following operating procedure: the dry mature seed of Semen Cuscutae is pulverized by (a), extract with 80～90% alcohol heat reflux, united extraction liquid, it is concentrated into without alcohol taste, successively with petroleum ether, ethyl acetate and water saturated n-butanol extraction, respectively obtain petroleum ether extract, acetic acid ethyl ester extract and n-butyl alcohol extract；B acetic acid ethyl ester extract macroporous resin remove impurity in () step (a), first with 6 column volumes of 10% ethanol elution, then with 10 column volumes of 75% ethanol elution, collects 75% ethanol elution, concentrating under reduced pressure obtains 75% ethanol elution thing extractum；In (c) step (b) 75% ethanol elution extractum with purification on normal-phase silica gel separate, successively with volume ratio be 80:1,55:1,30:1,15:1 and 1:1 methylene chloride-methanol gradient elution obtain 5 components；D in () step (c), component 4 separates further by purification on normal-phase silica gel, successively with volume ratio be 20:1,15:1 and 10:1 methylene chloride-methanol gradient elution obtain 3 components；E reverse phase silica gel that in () step (d), component 2 is bonded by octadecylsilane separates, with the methanol aqueous solution isocratic elution that concentration expressed in percentage by volume is 75%, collecting 8～10 column volume eluents, eluent concentrating under reduced pressure obtains compound (I).
4. the preparation method of compound according to claim 3 (I), it is characterised in that: described macroporous resin is AB-8 type macroporous adsorbent resin.
5. the preparation method of compound according to claim 3 (I), it is characterised in that: it is 85% that described alcohol heat reflux extracts the concentration of alcohol adopted.
6. the application in preparation agricultural herbicide of the compound (I) described in claim 1 or 2.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114671837A (en) * | 2022-04-11 | 2022-06-28 | 沈阳农业大学 | Eucalyptus alkane type sesquiterpenoids in ragweed and preparation method and application thereof |
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Application publication date: 20160720 |