CN102283197A - Application of o-hydroxybenzoic acid lactone compounds to alleviation of poisoning of amide herbicides on paddy rice - Google Patents
Application of o-hydroxybenzoic acid lactone compounds to alleviation of poisoning of amide herbicides on paddy rice Download PDFInfo
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- CN102283197A CN102283197A CN2011102245550A CN201110224555A CN102283197A CN 102283197 A CN102283197 A CN 102283197A CN 2011102245550 A CN2011102245550 A CN 2011102245550A CN 201110224555 A CN201110224555 A CN 201110224555A CN 102283197 A CN102283197 A CN 102283197A
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Abstract
The invention relates to o-hydroxybenzoic acid lactone compounds for alleviating the poisoning effect of amide herbicides on paddy rice and application thereof, and provides o-hydroxybenzoic acid lactone compounds and stereoisomers and compositions thereof which are taken as detoxicants of the amide herbicides. The o-hydroxybenzoic acid lactone compounds are taken as active ingredients and are combined with one or more processing acceptable carriers or are combined with the amide herbicides and one or more processing acceptable carriers, wherein the weight content of the active ingredients is 0.1 to 99.9 percent. Monomer substances with detoxification activity are extracted and separated from plants and are purified; the substances with detoxification activity are subjected to chemical synthesis and structural optimization; and an important way is provided for the development of safeners.
Description
Technical field
The present invention relates to a kind of acetamide-group herbicides of alleviating to septichen lactone compound of paddy rice toxic action and uses thereof.
Background technology
Acetamide-group herbicides are selective herbicides of a kind of efficient, wide spectrum, are mainly used in dry crop and prevent and kill off annual gramineous weed and part broad leaved weed.Acetamide-group herbicides activity in the paddy field is high especially.But because paddy rice is responsive unusually to most of acetamide-group herbicides, acetamide-group herbicides produce poisoning to the tender paddy rice of children easily when paddy field uses, make the application of acetamide-group herbicides in paddy field be subjected to strict restriction.Herbicide-safener is that a class can reduce weed killer herbicide to Toxicity in Crops; by increasing the tolerance of sensitive crop; alleviate or eliminate the injury of weed killer herbicide crop; has unique material; it do not influence weed killer herbicide to the prerequisite of target weeds activity under selectively cover crop exempt from the poisoning that is subjected to weed killer herbicide, thereby make the scope of quoting of many weed killer herbicides obtain enlarging, so promptly can be old kind new application prospect be provided; increase the service life, help the exploitation of novel herbicide again.Commercial at present chloro acetyl ammonia herbicide-safener has benoxacor, cyometrinil, oxabetrinil, naphthalene dimethyl anhydride etc.The country of research mainly contains the U.S., Switzerland, Germany, Japan and Canadian, and states such as Russia, Hungary are also in research.China also pays special attention to this problem, but the synthetic and bioactivity research of relevant safener still is in the starting stage.From plant, extract separation and purification and have the monomeric substance of detoxicating activity, and carry out chemosynthesis and structure optimization, for the exploitation of safener provides an important approach at material with detoxicating activity.
Summary of the invention
The invention provides septichen lactone compound and stereoisomer thereof and composition thereof, as the antipoison of acetamide-group herbicides.
Shown in the septichen lactone compound general formula provided by the present invention (I):
Wherein: R
1And R
0Be the hydrogen base, hydroxyl, n-butene base, normal butane base, (1-carbonyl) normal butane base or (2-hydroxyl) normal butane base a kind of or two kinds; R
2, R
4, R
5And R
7Be hydroxyl, or the hydrogen base, or the chloro base, or (1-carbonyl) normal butane base; R
3And R
6Be singly-bound or two key.
Be present in the plant corpus in above-mentioned septichen lactone compound and the stereoisomer thereof, comprise following three aspects:
1. work as R
3Be singly-bound, R
6During for two key, R
1And R
0Be respectively normal butane base and hydroxyl, or (1-carbonyl) normal butane base and hydroxyl, or (2-hydroxyl) normal butane base and hydrogen base or be combined into a n-butene base, R
2, R
4, R
5And R
7Be hydrogen; Perhaps R
1And R
0Be respectively normal butane base and hydrogen base, R
2Be monohydroxy, R
4, R
5And R
7Be the hydrogen base.
2. work as R
3And R
6During for two key, R
1And R
0Merge into the n-butene base, R
4And R
7Be respectively hydrogen base and hydrogen base, or hydroxyl and hydrogen base, or hydrogen base and hydroxyl, R
2And R
5Be the hydrogen base; Perhaps R
1And R
0Be respectively normal butane base and hydrogen base, R
2And R
7Be respectively hydrogen base and hydrogen base, or hydroxyl and hydroxyl, R
4And R
5Be the hydrogen base; Perhaps R
1Be (2-hydroxyl) n-butene base, R
2, R
4, R
5, R
7Be the hydrogen base.
3. work as R
3And R
6During for singly-bound, R
1And R
0Merge into the n-butene base, R
5And R
7Be respectively hydroxyl and hydroxyl, or hydroxyl and chloro base or (2-carbonyl) normal-butyl and hydroxyl, R
2And R
4Be the hydrogen base; Perhaps R
1And R
0Be respectively normal butane base and hydrogen base or normal butane base and hydroxyl, R
5And R
7Be hydroxyl, R
2And R
4Be the hydrogen base.
This compounds can obtain with the mode of chemosynthesis, and wherein part is distributed in botanic many plants, can extract separate to prepare and obtain from plant.
The compound composition that the present invention proposes comprises composition A and composition B.Composition A is an active component with the septichen lactone compound, goes up the acceptable carrier combination with one or more processing; Composition B is active component and acetamide-group herbicides and upward acceptable carrier combination of one or more processing with the septichen lactone compound, and wherein, the weight content of active component is 0.1~99.9%.
Processing of the present invention can be accepted carrier and mean the material that satisfies following condition: being convenient to try out the site in pending after carrier and the active component preparation, for example can be plant, seed or soil; Perhaps help storing, transport or operation; It can be the farm chemical carrier of formulations of pesticide manufacture field routine, for example agriculturals such as dispersant, wetting agent, binding agent, surfactant and auxiliary agent go up the acceptable carrier, these dispersants, wetting agent, binding agent, surfactant and auxiliary agent respectively have characteristic, and those skilled in the art can know.
Septichen lactone compound of the present invention and composition A thereof are applied to separately in the paddy rice or soil of using superamide class weed killer herbicide, perhaps with after making up with acetamide-group herbicides list agent (or composite dose) are applied in paddy rice or the soil; The composition B that perhaps contains the weed killer herbicide of safener directly is applied in paddy rice or the soil.Effectively the safe handling amount is a 1-5000 gram/mu.
Processing mentioned above can be accepted carrier and mean the material that satisfies following condition: being convenient to be applied to pending site after carrier and the active component preparation, for example can be plant, seed, soil or thin river sand; Perhaps help storing, transport or operation; Can be the farm chemical carrier of formulations of pesticide manufacture field routine, for example agriculturals such as emulsifier, dispersant, wetting agent bleeding agent, cosolvent, stabilizing agent and synergist go up the acceptable carrier.
The example of composition emulsifier carrier comprises as mentioned above: 1) citric acid and the tartaric derivative of the alkylphenol polyoxyethylene of nonionic, styryl phenol polyethenoxy ether, benzylphenol APEO, castor oil polyoxyethylene ether, fatty alcohol-polyoxyethylene ether, polyoxyethylene carboxylate, aliphatic amine polyoxyethylene ether, poly-alkylglycoside and fatty alcohol-polyoxyethylene ether; 2) sulfonate of the benzene sulfonamide amine acid salt of anionic, alkylsulfonate, succinic acid, alkane naphthalene sulfonate.
The example of dispersant carrier comprises: fatty alcohol-polyoxyethylene ether, polyoxyethylene carboxylate, aliphatic amine polyoxyethylene ether, fatty acid amide APEO, alkylphenol polyoxyethylene, fatty acid glyceride APEO, vegetable oil ethylene oxide adduct and derivative, hexamethylene diamine polyoxyethylene poly-oxygen propylene aether, ethylene oxide-propylene oxide block copolymer, alkylphenol polyoxyethylene formaldehyde condensation products and alkylphenol-polyethenoxy polyethenoxy ether.
The example of wetting agent bleeding agent carrier comprises: 1) natural saponin; 2) aliphatic alcohol sulfate of anionic, benzene sulfonamide acid alkali metal and amine salt, dialkyl group succinate sulfonate sodium, fatty alcohol, the sulfonate of alkylphenol polyoxyethylene succinic acid, alkylphenol polyoxyethylene formaldehyde condensation products succinic acid half ester sulfonate, fatty acid amide N methyl taurine sodium salt, sodium sulfate of polyethenoxy ether of fatty alcohol, alkylphenol polyoxyethylene sulphate, Negel, fatty acid or fatty acid ester sulphate, sodium lignin sulfonate, petroleum sodium sulfonate and polymerization of carboxylic acid sodium; 3) alkylphenol polyoxyethylene of nonionic, fatty alcohol-polyoxyethylene ether, polyoxyethylene polyoxypropylene block copolymer and aliphatic acid polyethenoxy monoesters; 4) and cationic alkyl (C
12-C
24Alkyl) benzyl dimethyl ammonium chloride, alkyl (C
12-C
18Alkyl) pyridinium halide, alkyl (C
12H
25Deng) amine oxide.
The example of cosolvent carrier comprises: aromatic hydrocarbons (toluene, dimethylbenzene and naphthalene etc.), aliphatic hydrocarbon, alicyclic, alcohol (methyl alcohol, ethanol, propyl alcohol, isopropyl alcohol, butanols etc.), fatty acid ester, ketone (cyclohexanone, MEK and acetone etc.) and ether (glycol ether and propylene glycol etc.).
The example of stabilizing agent carrier comprises: organophosphorus compounds stabilizing agent (alkyl phosphate and derivative thereof, alkylamine EOization thing phosphate and other phosphate etc.), EO addition product and derivative ethers and solvent-stable agent.
The example of synergist carrier comprises: alkylamine and amides compound, propine ether and ester class and organophosphorus ester and carbamate.
Utilize the septichen lactone compound can effectively reduce the injury of acetamide-group herbicides to paddy rice, the while is management of weeds effectively.
Concrete embodiment
The following examples are to further specify of the present invention, but all should not be viewed as the restriction of by any way range of application of the present invention being carried out in any case.
(3-Butylidene-4 is 5-dihydrophthalide) with senkyunolide A (3-N-Butyl-4, preparation 5-dihydrophthalide) for ligustilide in the example 1 compound general formula (I).Step is as follows:
1) Rhizoma Chuanxiong power is broken into powder, crosses 100 mesh sieves;
2) ℃ freeze drying then-40;
3) the 6kg Ligusticum wallichii is through carbon dioxide supercritical extraction, and extraction temperature and pressure are respectively 50 ℃ and 35MP, and separation temperature and pressure are respectively 55 ℃ and 8MP, do not add entrainment reagent, obtain the 0.2kg extract, and yield is 3.3%;
4) separate through high speed adverse current chromatogram (HSCCC), obtain four components (three monomeric substance Q1, Q2 and Q3 and a mixture), Q1, Q2 and Q3 detect purity through high performance liquid chromatography (HPLC) and surpass 95%, separating selected dicyandiamide solution is n-hexane: ethyl acetate: ethanol: water (5: 4: 3: 2, v/v/v/v), flow velocity is 1.5ml/min, and rotating speed is 900r/min, and temperature is 26 ℃;
5) determine active substance Q1, Q2, Spectrum Analysis technology such as mensuration by functional group and ultraviolet spectra, infrared spectrum, nuclear magnetic resoance spectrum, mass spectrum have been carried out the structure evaluation to Q1, Q2, ligustilide and senkyunolide A in being defined as, molecular weight is respectively 190 and 192.
Example 2 ligustilides and senkyunolide A are alleviated the experimental technique of acetamide-group herbicides isopropyl methoxalamine to the paddy rice toxic action
For the rice of trying the water is that strain two is excellent 90, disinfects through clorox before using, and soil is the sterilizing-drying soil that does not have chemical substance such as agricultural chemicals to pollute.Take by weighing 180g soil and put into the Culture basin of 110cm2, add the water mixing, the use unanimity of the water yield of every basin, every basin is sowed the consistent rice seedling of 20 strains germination, and paddy rice is cultivated in illumination box.
Paddy rice is long wholeheartedly to begin the dispenser processing to a leaf.The smart isopropyl methoxalamine of ligustilide, senkyunolide A and weed killer herbicide is dissolved in the acetone, is dispersed in the water with Tween-80 then.5mL0.01g/L weed killer herbicide is evenly distributed on soil surface with pouring into after 10mL ligustilide (a series of concentration are: 1g/L, 2g/L, 4g/L, 8g/L, 16g/L and 32g/L) and senkyunolide A (a series of concentration are: 1g/L, 2g/L, 4g/L, 8g/L, 16g/L and 32g/L) mix respectively in the Culture basin.Triplicate, if safener contrast, the weed killer herbicide contrast, the clear water contrast, after the dispenser, continuation with the growth of same condition, is measured paddy rice plant height and fresh weight after 8 days in illumination box, the result shows that ligustilide and senkyunolide A can obviously alleviate the toxic action (table 1 and table 2) of the smart isopropyl methoxalamine of acetamide-group herbicides to paddy rice.
Table 1 ligustilide is removed the effect that isopropyl methoxalamine is poisoned paddy rice
The isopropyl methoxalamine consumption | The ligustilide consumption | Average plant height | The strain fresh weight |
(g/L) | (g/L) | (cm) | (g/10 strain) |
0 | 0 | 23.97 | 1.441 |
0.1 | 0 | 6.26 | 0.889 |
0.1 | 1 | 12.85(205.27) * | 1.024(115.18) |
0.1 | 2 | 15.94(254.63) | 1.142(128.48) |
0.1 | 4 | 18.39(293.76) | 1.367(153.76) |
0.1 | 8 | 19.56(312.46) | 1.384(155.68) |
0.1 | 16 | 20.12(321.24) | 1.373(154.44) |
0.1 | 32 | 18.99(303.35) | 1.409(158.49) |
Annotate: * represents growth rate
Table 2 senkyunolide A removes the effect that isopropyl methoxalamine is poisoned paddy rice
The isopropyl methoxalamine consumption | Senkyunolide A consumption | Average plant height | The strain fresh weight |
(g/L) | (g/L) | (cm) | (g/10 strain) |
0 | 0 | 23.9 | 1.441 |
0.1 | 0 | 6.26 | 0.889 |
0.1 | 1 | 10.81(172.68) * | 1.002(112.71) |
0.1 | 2 | 13.99(223.48) | 1.142(128.45) |
0.1 | 4 | 15.97(255.11) | 1.267(142.51) |
0.1 | 8 | 17.83(284.82) | 1.284(144.43) |
0.1 | 16 | 18.23(291.21) | 1.273(143.19) |
0.1 | 32 | 18.18(290.41) | 1.209(135.99) |
Annotate: * represents growth rate
Claims (5)
1. the purposes of a septichen lactone compound or its stereoisomer, it is characterized in that: described septichen lactone compound is as the antipoison of acetamide-group herbicides, shown in its general formula (I):
Wherein: R
1And R
0Be the hydrogen base, hydroxyl, n-butene base, normal butane base, (1-carbonyl) normal butane base or (2-hydroxyl) normal butane base a kind of or two kinds; R
2, R
4, R
5And R
7Be hydroxyl, or the hydrogen base, or the chloro base, or (1-carbonyl) normal butane base; R
3And R
6Be singly-bound or two key;
Above-mentioned septichen lactone compound and stereoisomer thereof are present in the plant corpus, comprise following three aspects:
(1) works as R
3Be singly-bound, R
6During for two key, R
1And R
0Be respectively normal butane base and hydroxyl, or (1-carbonyl) normal butane base and hydroxyl, or (2-hydroxyl) normal butane base and hydrogen base or be combined into a n-butene base, R
2, R
4, R
5And R
7Be hydrogen; Perhaps R
1And R
0Be respectively normal butane base and hydrogen base, R
2Be monohydroxy, R
4, R
5And R
7Be the hydrogen base;
(2) work as R
3And R
6During for two key, R
1And R
0Merge into the n-butene base, R
4And R
7Be respectively hydrogen base and hydrogen base, or hydroxyl and hydrogen base, or hydrogen base and hydroxyl, R
2And R
5Be the hydrogen base; Perhaps R
1And R
0Be respectively normal butane base and hydrogen base, R
2And R
7Be respectively hydrogen base and hydrogen base, or hydroxyl and hydroxyl, R
4And R
5Be the hydrogen base; Perhaps R
1Be (2-hydroxyl) n-butene base, R
2, R
4, R
5, R
7Be the hydrogen base;
(3) work as R
3And R
6During for singly-bound, R
1And R
0Merge into the n-butene base, R
5And R
7Be respectively hydroxyl and hydroxyl, or hydroxyl and chloro base or (2-carbonyl) normal-butyl and hydroxyl, R
2And R
4Be the hydrogen base; Perhaps R
1And R
0Be respectively normal butane base and hydrogen base or normal butane base and hydroxyl, R
5And R
7Be hydroxyl, R
2And R
4Be the hydrogen base.
2. the purposes of a kind of compound according to claim 1 or its stereoisomer, it is characterized in that: described septichen lactone compound and other material form composition, comprise composition A and composition B, composition A is an active component with the septichen lactone compound, goes up the acceptable carrier combination with one or more processing; Composition B is active component and acetamide-group herbicides and upward acceptable carrier combination of one or more processing with the septichen lactone compound, and wherein, the weight content of active component is 0.1~99.9%.
3. the purposes of a kind of compound according to claim 2 or its stereoisomer, it is characterized in that: described processing can be accepted carrier and mean the material that satisfies following condition: be convenient to try out the site in pending after carrier and the active component preparation, plant or seed or soil; Perhaps help storing, transport or operation; Or the farm chemical carrier of formulations of pesticide manufacture field routine, for example emulsifier, dispersant, wetting agent, stabilizing agent, synergist and auxiliary agent.
4. the purposes of a kind of compound according to claim 2 or its stereoisomer, it is characterized in that: described septichen lactone compound and composition A thereof are applied to separately in the paddy rice or soil of using superamide class weed killer herbicide, perhaps with after acetamide-group herbicides list agent (or the composite dose) combination are applied in paddy rice or the soil; The composition B that perhaps contains the weed killer herbicide of safener directly is applied in paddy rice or the soil; Effectively the safe handling amount is a 1-5000 gram/mu.
5. according to the purposes of claim 2 or 3 described a kind of compounds or its stereoisomer, it is characterized in that: the example of described emulsifier carrier comprises: the citric acid and the tartaric derivative of the alkylphenol polyoxyethylene of (1) nonionic, styryl phenol polyethenoxy ether, benzylphenol APEO, castor oil polyoxyethylene ether, fatty alcohol-polyoxyethylene ether, polyoxyethylene carboxylate, aliphatic amine polyoxyethylene ether, poly-alkylglycoside and fatty alcohol-polyoxyethylene ether; (2) sulfonate of the benzene sulfonamide amine acid salt of anionic, alkylsulfonate, succinic acid, alkane naphthalene sulfonate;
The example of dispersant carrier comprises: fatty alcohol-polyoxyethylene ether, polyoxyethylene carboxylate, aliphatic amine polyoxyethylene ether, fatty acid amide APEO, alkylphenol polyoxyethylene, fatty acid glyceride APEO, vegetable oil ethylene oxide adduct and derivative, hexamethylene diamine polyoxyethylene poly-oxygen propylene aether, ethylene oxide-propylene oxide block copolymer, alkylphenol polyoxyethylene formaldehyde condensation products and alkylphenol-polyethenoxy polyethenoxy ether;
The example of wetting agent bleeding agent carrier comprises: the saponin that (1) is natural; (2) aliphatic alcohol sulfate of anionic, benzene sulfonamide acid alkali metal and amine salt, dialkyl group succinate sulfonate sodium, fatty alcohol, the sulfonate of alkylphenol polyoxyethylene succinic acid, alkylphenol polyoxyethylene formaldehyde condensation products succinic acid half ester sulfonate, fatty acid amide N methyl taurine sodium salt, sodium sulfate of polyethenoxy ether of fatty alcohol, alkylphenol polyoxyethylene sulphate, Negel, fatty acid or fatty acid ester sulphate, sodium lignin sulfonate, petroleum sodium sulfonate and polymerization of carboxylic acid sodium; (3) alkylphenol polyoxyethylene of nonionic, fatty alcohol-polyoxyethylene ether, polyoxyethylene polyoxypropylene block copolymer and aliphatic acid polyethenoxy monoesters; (4) and cationic alkyl (C
12-C
24Alkyl) benzyl dimethyl ammonium chloride, alkyl (C
12-C
18Alkyl) pyridinium halide, alkyl (C
12H
25) amine oxide;
The example of cosolvent carrier comprises: aromatic hydrocarbons (toluene, dimethylbenzene and naphthalene), aliphatic hydrocarbon, alicyclic, alcohol (methyl alcohol, ethanol, propyl alcohol, isopropyl alcohol, butanols), fatty acid ester, ketone (cyclohexanone, MEK and acetone) and ether (glycol ether and propylene glycol);
The example of stabilizing agent carrier comprises: organophosphorus compounds stabilizing agent (alkyl phosphate and derivative thereof, alkylamine EOization thing phosphate and other phosphate), EO addition product and derivative ethers and solvent-stable agent;
The example of synergist carrier comprises: alkylamine and amides compound, propine ether and ester class and organophosphorus ester and carbamate.
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Cited By (3)
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CN106804589A (en) * | 2016-12-31 | 2017-06-09 | 新昌县鼎兴生物技术有限公司 | Septichen lactone compound alleviates the purposes that acetamide-group herbicides are poisoned to paddy rice |
CN110772510A (en) * | 2019-12-13 | 2020-02-11 | 浙江省淡水水产研究所 | Novel application of ligustilide |
CN110800744A (en) * | 2019-11-06 | 2020-02-18 | 兰州大学 | Application of phthalide compounds in angelica sinensis in preventing and treating agricultural diseases |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106804589A (en) * | 2016-12-31 | 2017-06-09 | 新昌县鼎兴生物技术有限公司 | Septichen lactone compound alleviates the purposes that acetamide-group herbicides are poisoned to paddy rice |
CN110800744A (en) * | 2019-11-06 | 2020-02-18 | 兰州大学 | Application of phthalide compounds in angelica sinensis in preventing and treating agricultural diseases |
CN110772510A (en) * | 2019-12-13 | 2020-02-11 | 浙江省淡水水产研究所 | Novel application of ligustilide |
CN110772510B (en) * | 2019-12-13 | 2022-07-19 | 浙江省淡水水产研究所 | Application of ligustilide |
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Application publication date: 20111221 |