CN114794105B - Application of carane-3, 4-diol as or in preparation of herbicide - Google Patents
Application of carane-3, 4-diol as or in preparation of herbicide Download PDFInfo
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- CN114794105B CN114794105B CN202210661602.6A CN202210661602A CN114794105B CN 114794105 B CN114794105 B CN 114794105B CN 202210661602 A CN202210661602 A CN 202210661602A CN 114794105 B CN114794105 B CN 114794105B
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- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 41
- 239000004009 herbicide Substances 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims description 7
- AHVKNBRJVKCGKJ-UHFFFAOYSA-N 4,7,7-trimethylbicyclo[4.1.0]heptane-3,4-diol Chemical compound C1C(O)C(C)(O)CC2C(C)(C)C21 AHVKNBRJVKCGKJ-UHFFFAOYSA-N 0.000 title abstract description 30
- 241000196324 Embryophyta Species 0.000 claims abstract description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- BQOFWKZOCNGFEC-UHFFFAOYSA-N carene Chemical compound C1C(C)=CCC2C(C)(C)C12 BQOFWKZOCNGFEC-UHFFFAOYSA-N 0.000 claims abstract description 13
- 241000209082 Lolium Species 0.000 claims abstract description 10
- 244000234609 Portulaca oleracea Species 0.000 claims abstract description 10
- 235000001855 Portulaca oleracea Nutrition 0.000 claims abstract description 10
- 244000042324 Trifolium repens Species 0.000 claims abstract description 10
- 235000013540 Trifolium repens var repens Nutrition 0.000 claims abstract description 10
- 235000010086 Setaria viridis var. viridis Nutrition 0.000 claims abstract description 9
- 244000025670 Eleusine indica Species 0.000 claims abstract description 8
- 235000014716 Eleusine indica Nutrition 0.000 claims abstract description 8
- 235000014820 Galium aparine Nutrition 0.000 claims abstract description 8
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 7
- 244000058871 Echinochloa crus-galli Species 0.000 claims abstract 2
- 244000230342 green foxtail Species 0.000 claims abstract 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 claims description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 5
- 229920000053 polysorbate 80 Polymers 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- ZNZZFXONMYVVGZ-UHFFFAOYSA-N heptane-3,4-diol Chemical compound CCCC(O)C(O)CC ZNZZFXONMYVVGZ-UHFFFAOYSA-N 0.000 claims description 2
- 240000004658 Medicago sativa Species 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 210000001161 mammalian embryo Anatomy 0.000 abstract description 12
- 230000035784 germination Effects 0.000 abstract description 9
- 231100000053 low toxicity Toxicity 0.000 abstract description 8
- 238000011161 development Methods 0.000 abstract description 7
- 230000018109 developmental process Effects 0.000 abstract description 7
- 229930006737 car-3-ene Natural products 0.000 abstract description 4
- 244000144972 livestock Species 0.000 abstract description 4
- 238000012827 research and development Methods 0.000 abstract description 4
- 239000004593 Epoxy Substances 0.000 abstract description 3
- 238000005906 dihydroxylation reaction Methods 0.000 abstract description 3
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 3
- 238000007142 ring opening reaction Methods 0.000 abstract description 3
- 239000003905 agrochemical Substances 0.000 abstract description 2
- BWRHOYDPVJPXMF-UHFFFAOYSA-N carane group Chemical group C12CC(CCC1C2(C)C)C BWRHOYDPVJPXMF-UHFFFAOYSA-N 0.000 abstract description 2
- 241000192043 Echinochloa Species 0.000 description 8
- 241000219823 Medicago Species 0.000 description 8
- 244000304962 green bristle grass Species 0.000 description 7
- 229930003658 monoterpene Natural products 0.000 description 7
- 235000002577 monoterpenes Nutrition 0.000 description 7
- -1 Monoterpene compounds Chemical class 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- 238000012360 testing method Methods 0.000 description 5
- 241000255925 Diptera Species 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000012488 sample solution Substances 0.000 description 4
- 239000000341 volatile oil Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 239000008223 sterile water Substances 0.000 description 3
- 238000009333 weeding Methods 0.000 description 3
- 240000002791 Brassica napus Species 0.000 description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 2
- 241000779819 Syncarpia glomulifera Species 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 239000012490 blank solution Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- LMXFTMYMHGYJEI-UHFFFAOYSA-N p-menthane-3,8-diol Chemical compound CC1CCC(C(C)(C)O)C(O)C1 LMXFTMYMHGYJEI-UHFFFAOYSA-N 0.000 description 2
- 239000001739 pinus spp. Substances 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- 230000002940 repellent Effects 0.000 description 2
- 230000001846 repelling effect Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000002791 soaking Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229940036248 turpentine Drugs 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- MMBISVTWDPWUDW-UHFFFAOYSA-N 4,7,7-trimethylbicyclo[4.1.0]hept-5-ene-3,4-diol Chemical compound C1C(O)C(C)(O)C=C2C(C)(C)C21 MMBISVTWDPWUDW-UHFFFAOYSA-N 0.000 description 1
- 240000002245 Acer pensylvanicum Species 0.000 description 1
- 235000006760 Acer pensylvanicum Nutrition 0.000 description 1
- 235000014698 Brassica juncea var multisecta Nutrition 0.000 description 1
- 235000011293 Brassica napus Nutrition 0.000 description 1
- 235000006008 Brassica napus var napus Nutrition 0.000 description 1
- 235000006618 Brassica rapa subsp oleifera Nutrition 0.000 description 1
- 244000188595 Brassica sinapistrum Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- 244000004281 Eucalyptus maculata Species 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000000983 citronellal Nutrition 0.000 description 1
- 229930003633 citronellal Natural products 0.000 description 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
- 238000012136 culture method Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- 150000002773 monoterpene derivatives Chemical class 0.000 description 1
- 239000010413 mother solution Substances 0.000 description 1
- 229930006948 p-menthane-3,8-diol Natural products 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229930000044 secondary metabolite Natural products 0.000 description 1
- 230000007226 seed germination Effects 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/06—Oxygen or sulfur directly attached to a cycloaliphatic ring system
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses an application of carane-3, 4-diol in serving as or preparing herbicide, belonging to the technical field of agricultural chemical research and development. The carane-3, 4-diol is a product of 3-carene dihydroxylation or epoxy ring-opening hydrolysis reaction, has a lipophilic carane skeleton structure and two hydrophilic hydroxyl groups, can be dissolved or dispersed in water under the action of no auxiliary agent or a small amount of auxiliary agent, and can obviously inhibit the elongation of the germination radicle and embryo of various common monocotyledonous or dicotyledonous plant seeds such as green bristlegrass, purslane, barnyard grass, goosegrass, ryegrass, white clover, rape and the like. The carane-3, 4-diol has low toxicity to human and livestock, is safe to ecological environment, has high efficiency and low toxicity, and can be used as a plant source water-based herbicide or used for preparing the herbicide to prevent and remove weeds. In addition, the development of the herbicidal effect of the carane-3, 4-diol can promote the comprehensive development and utilization of the forest resources rich in 3-carene, and has wide development prospect.
Description
Technical Field
The invention belongs to the technical field of agricultural chemical research and development, and particularly relates to application of carane-3, 4-diol as or in preparation of herbicide.
Background
The herbicide plays an important role in modern agriculture, can effectively prevent and control weed harm, increase crop yield, improve agricultural product quality, lighten labor intensity and improve production efficiency; in addition, with the enhancement of people's awareness of food safety and ecological environment protection, research and development of efficient low-toxicity herbicides, especially plant-source herbicides and green environment-friendly water-based formulations thereof, have become current national policy requirements and industry development consensus.
Monoterpene compounds (monoterpenes) are secondary metabolites of many plants, generally show good biological activity, for example, the monoterpene compounds containing two hydroxyl groups, such as the monoterpene compounds, also can be ascribed to monoterpene diols (monoterpene diol), are naturally existing in lemon eucalyptus branch and leaf essential oil, can also be prepared by taking some plant essential oil components such as citronellal, crotonaldehyde, menthol and the like as raw materials through chemical or biological conversion, have good biological activity of mosquito repelling, weeding and the like, and are commercially developed and applied as efficient low-toxicity mosquito repelling agents at present. However, the natural sources are insufficient, the synthetic raw materials are expensive, and the wider popularization and application of the p-menthane-3, 8-diol are limited.
The carane-3, 4-diol is also a monoterpene diol, has a small content in nature, but can be prepared from certain turpentine and main components 3-carene of plant volatile oil through epoxy ring-opening hydrolysis or dihydroxylation reaction, for example, chinese patent application No. 201010590859.4 discloses a preparation method of the mosquito and fly repellent 3, 4-carene diol. The molecular structure of the carane-3, 4-diol contains 1 lipophilic carane structure and 2 hydrophilic hydroxyl groups, is slightly soluble in water, has mosquito and fly repellent and insecticidal activity and moisturizing effect, is safe to people and livestock and environment, has low toxicity and obviously lower price than the p-menthane-3, 8-diol, and is expected to play a larger role in green pesticides. However, up to now, there are studies on the herbicidal activity and application of Guan alkane-3, 4-diol, and no related reports have been made in the literature at home and abroad.
Disclosure of Invention
The present invention aims to address the above-mentioned drawbacks and deficiencies of the prior art by providing the use of carane-3, 4-diol as or in the preparation of herbicides. The invention discovers that the carane-3, 4-diol has herbicidal activity for the first time, can inhibit the elongation of the germination radicle and embryo of various monocotyledonous or dicotyledonous plant seeds such as barnyard grass, ryegrass, green bristlegrass, goosefoot, purslane, alfalfa, white clover, rape and the like, has good herbicidal activity, is safe to human and livestock and environment, has low toxicity, and can be used as a plant source water-based herbicide or used for preparing the herbicide.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
use of carene-3, 4-diol as or in the preparation of a herbicide, said carene-3, 4-diol having the molecular structure of formula (1) as follows, under the chemical name (IUPC nomenclature): (1S, 3R,4R, 6R) -3, 7-trimethylbicyclo [4.1.0] heptane-3, 4-diol.
Furthermore, the carane-3, 4-diol can be dissolved or dispersed in water under the action of no or a small amount of auxiliary agent to prepare aqueous solution or emulsion, and can be used as herbicide to inhibit the elongation of germination radicle and embryo of various common weed seeds; the auxiliary agent refers to a hydrophilic solvent and a surfactant, and comprises one or more than 2 mixtures of N, N-dimethylformamide, dimethyl sulfoxide, ethylene glycol, propylene glycol and tween-80.
Preferably, the herbicide in the application comprises a plurality of monocotyledonous or dicotyledonous plants such as barnyard grass, ryegrass, green bristlegrass, goosegrass, purslane, alfalfa, white clover, rape and the like.
A herbicide containing carane-3, 4-diol is also within the scope of the present invention.
In the research process, the inventor finds that the carane-3, 4-diol can obviously inhibit the extension of the germination radicle and embryo of a plurality of monocotyledonous or dicotyledonous plant seeds such as barnyard grass, ryegrass, green bristlegrass, goosegrass, purslane, alfalfa, white clover, rape and the like through multiple experiments, has good weeding activity, and can be used as a herbicide or used for preparing the herbicide.
The beneficial effects of the invention are as follows:
(1) The invention discloses a new application of carane-3, 4-diol in the aspect of serving as or preparing herbicide, and researches show that the carane-3, 4-diol has obvious herbicidal activity, can inhibit the elongation of germination radicle and embryo of various monocotyledonous or dicotyledonous plant seeds such as barnyard grass, ryegrass, green bristlegrass, goosegrass, purslane, alfalfa, white clover, rape and the like, and has good herbicidal activity.
(2) The carane-3, 4-diol is the product of 3-carane dihydroxylation or epoxy ring-opening hydrolysis reaction, and the synthetic raw material 3-carane is derived from natural plants and is low in cost and easy to obtain; the carane-3, 4-diol has low toxicity to human and livestock, is safe to ecological environment, has no pollution, no residue, high efficiency and low toxicity, and can be used as a plant source water-based herbicide or used for preparing the herbicide to prevent and remove weeds.
(3) The research and development of the herbicidal effect of the carane-3, 4-diol not only provides a new raw material source for the development of the plant source herbicide, but also promotes the comprehensive development and utilization of turpentine and plant volatile oil resources containing 3-carene, and has wide development prospect.
Detailed Description
The present invention is further illustrated below with reference to specific examples, which are not intended to limit the invention in any way. Unless specifically stated otherwise, the reagents, methods and apparatus employed in the present invention are those conventional in the art.
The reagents and materials used in the following examples are commercially available unless otherwise specified.
Test method for herbicidal activity of carane-3, 4-diol against several common weeds:
1. preparing a sample mother solution: weighing 2mmol of carane-3, 4-diol, dissolving with 0.5mL of N, N-dimethylformamide, transferring into a 100mL volumetric flask, adding 5mL of 1% Tween-80 emulsifier, diluting with sterile distilled water to constant volume, and mixing thoroughly to obtain 20 mmol/L solution -1 Is used as a sample mother liquor.
2. Preparing a sample solution: firstly, 5mLN, N-dimethylformamide and 50mL of 1% Tween-80 are placed in a volumetric flask with 1L, sterile distilled water is used for constant volume, and uniformly mixed to prepare a blank solution, then mother liquor for sample is diluted according to a double dilution method to prepare a mother liquor with the concentration of 10, 5, 2.5, 1.25, 0.625 and 0.312 mmol.L -1 Is provided for a series of sample solutions.
3. Determination of herbicidal Activity: the method comprises the steps of adopting a plate culture method, firstly soaking seeds in a 2% sodium hypochlorite solution for sterilization for 5min, flushing for 3 times by using sterile water, soaking the seeds in the sterile water for 15h, then placing the seeds in a culture dish (the diameter is 9 cm) with two pieces of round filter paper placed at the bottom, adding a proper amount of sterile water, and placing the seeds in a climatic chamber for culture for 24h under the dark condition with the temperature of 25 ℃ and the humidity of 70%, so that the seeds germinate and become white. 10 seeds with germinated and exposed seeds are selected, placed in a culture dish with the diameter of 9cm and two round filter paper plates at the bottom, evenly distributed, 10mL of sample solution is poured into the culture dish, and three groups of repeated experiments are carried out on each concentration of sample solution and blank solution. Culturing the culture dish in artificial climatic box at 25deg.C under dark condition with humidity of 70% for 72 h, measuring the length of radicle and embryo, taking average value, calculating the inhibition rate of root and bud elongation according to the following formula, and if root length or bud length is less than 1mm, not counting and calculating.
Examples 1-4 are the sequential application of the herbicidal activity assay described above to common monocotyledonous weeds: test of herbicidal activity by barnyard grass, ryegrass, green bristlegrass and goosegrass.
Table 1 lists the herbicidal activity test results of examples 1 to 4 carane-3, 4-diol against several common monocotyledonous weeds at different concentrations. As can be seen from Table 1, the carane-3, 4-diol inhibits the elongation of barnyard grass, ryegrass, green bristlegrass and goosegrass seed germination radicle, embryo, exhibits herbicidal activity related to concentration, and increases with increasing concentration, when the concentration is 5.00 mmol -1 When the carane-3, 4-diol has the inhibition rates of 95.9, 100, 99.3 and 99.0 percent of the extension of the radicle of the germination of the seeds of barnyard grass, ryegrass, green bristlegrass and goosegrass, and the inhibition rates of 98.8, 85.6, 100 and 95.9 percent of the extension of the embryo.
Examples 5-8 are the sequential application of the herbicidal activity assay described above to common dicotyledonous weeds: test of herbicidal activity by purslane, alfalfa, white clover and canola.
Table 2 lists the herbicidal activity test results of examples 5 to 8 carane-3, 4-diol on several common dicotyledonous weeds at different concentrations (as shown in table 2). As can be seen from Table 2, the carane-3, 4-diol inhibits elongation of the germinal radicle and embryo of purslane, alfalfa, white clover and rape seed, exhibits herbicidal activity associated with concentration, and increases inhibition with increasing concentration, when the concentration is 10.0 mmol.L -1 When the carane-3, 4-diol has the inhibition rate of 96.3, 99.4, 100 and 100 percent of the elongation of the germination radicle of purslane, alfalfa, white clover and rape seeds, and the inhibition rate of 100, 84.6, 99.0 and 98.5 percent of the elongation of embryo bud.
The test results show that the carane-3, 4-diol can obviously inhibit the elongation of the germination radicle and embryo of a plurality of monocotyledonous or dicotyledonous plant seeds such as barnyard grass, ryegrass, purslane, alfalfa, white clover, rape and the like, has good weeding activity, and can be used as herbicide or used for preparing herbicide.
When the carane-3, 4-diol is specifically used, the carane-3, 4-diol can be dissolved or dispersed in water under the action of no or a small amount of auxiliary agent to prepare aqueous solution or emulsion, and can be used as herbicide to inhibit the elongation of the germination radicle and embryo of various common weed seeds; the auxiliary agent refers to a hydrophilic solvent and a surfactant, and comprises one or more than 2 mixtures of N, N-dimethylformamide, dimethyl sulfoxide, ethylene glycol, propylene glycol and tween-80.
Claims (3)
1. Use of carene-3, 4-diol as or in the preparation of a herbicide, said carene-3, 4-diol having the molecular structure of formula (1) as follows, under the chemical name: (1S, 3R,4R, 6R) -3, 7-trimethylbicyclo [4.1.0] heptane-3, 4-diol,
the herbicide has monocotyledonous or dicotyledonous plant as active target, and the monocotyledonous or dicotyledonous plant is barnyard grass, ryegrass, green bristlegrass, goosegrass herb, purslane, alfalfa, white clover and rape.
2. The use according to claim 1, wherein the carene-3, 4-diol is dissolved or dispersed in water without or with a small amount of an auxiliary agent to prepare an aqueous solution or emulsion.
3. The use according to claim 2, wherein the adjuvant is a hydrophilic solvent and a surfactant selected from one or more of N, N-dimethylformamide, dimethylsulfoxide, ethylene glycol, propylene glycol and tween-80.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5130136A (en) * | 1990-09-18 | 1992-07-14 | Sumitomo Chemical Company, Limited | Monoterpenediol insect repellents |
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| JPH0881307A (en) * | 1994-09-16 | 1996-03-26 | Sumitomo Chem Co Ltd | Noxious insect repellent |
| JPH0899806A (en) * | 1994-09-30 | 1996-04-16 | Sumitomo Chem Co Ltd | Repellent for insect pest |
| JPH0928388A (en) * | 1995-07-24 | 1997-02-04 | Sumitomo Chem Co Ltd | Production of carane-3,4-diol |
| JPH09221449A (en) * | 1996-02-13 | 1997-08-26 | Sumitomo Chem Co Ltd | Optical resolution of carboxylic acid having asymmetric carbon at alpha position |
| CN102060671A (en) * | 2010-12-16 | 2011-05-18 | 上海应用技术学院 | Method for preparing 3,4-carane diol as mosquito and fly evading agent |
| CN104649908A (en) * | 2013-11-18 | 2015-05-27 | 江苏扬农化工股份有限公司 | Pyrethroid compound with single spatial configuration, preparation method and application thereof |
| CN110447644A (en) * | 2019-09-09 | 2019-11-15 | 中国科学院新疆生态与地理研究所 | A kind of Monoterpene compound sabinene is preparing the application in herbicide |
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2022
- 2022-06-13 CN CN202210661602.6A patent/CN114794105B/en active Active
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5130136A (en) * | 1990-09-18 | 1992-07-14 | Sumitomo Chemical Company, Limited | Monoterpenediol insect repellents |
| WO1993020035A1 (en) * | 1992-04-03 | 1993-10-14 | Nippon Soda Co., Ltd. | Process for producing cyclopropane derivative |
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