CN113973824A - Use of cyclohexane-1, 3-diones as herbicides - Google Patents
Use of cyclohexane-1, 3-diones as herbicides Download PDFInfo
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- CN113973824A CN113973824A CN202111332014.XA CN202111332014A CN113973824A CN 113973824 A CN113973824 A CN 113973824A CN 202111332014 A CN202111332014 A CN 202111332014A CN 113973824 A CN113973824 A CN 113973824A
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- grass
- cyclohexane
- herbicides
- phenoxy
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- 239000004009 herbicide Substances 0.000 title claims abstract description 15
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical class O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 title description 4
- 241000196324 Embryophyta Species 0.000 claims abstract description 13
- 244000068988 Glycine max Species 0.000 claims abstract description 9
- 235000010469 Glycine max Nutrition 0.000 claims abstract description 9
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 8
- 235000007320 Avena fatua Nutrition 0.000 claims abstract description 6
- 235000004535 Avena sterilis Nutrition 0.000 claims abstract description 6
- 244000058871 Echinochloa crus-galli Species 0.000 claims abstract description 6
- 241001647031 Avena sterilis Species 0.000 claims abstract description 5
- 235000001602 Digitaria X umfolozi Nutrition 0.000 claims abstract description 5
- 235000017898 Digitaria ciliaris Nutrition 0.000 claims abstract description 5
- 235000005476 Digitaria cruciata Nutrition 0.000 claims abstract description 5
- 235000006830 Digitaria didactyla Nutrition 0.000 claims abstract description 5
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 claims abstract description 5
- 235000010823 Digitaria sanguinalis Nutrition 0.000 claims abstract description 5
- 244000025670 Eleusine indica Species 0.000 claims abstract description 5
- 235000014716 Eleusine indica Nutrition 0.000 claims abstract description 5
- 235000010086 Setaria viridis var. viridis Nutrition 0.000 claims abstract description 5
- 244000152045 Themeda triandra Species 0.000 claims abstract description 5
- 244000025254 Cannabis sativa Species 0.000 claims abstract description 4
- 244000230342 green foxtail Species 0.000 claims abstract 2
- 241000743985 Alopecurus Species 0.000 abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- ULXGJWWZHKJAMQ-UHFFFAOYSA-N 2-(4-chlorophenoxy)propan-1-ol Chemical compound OCC(C)OC1=CC=C(Cl)C=C1 ULXGJWWZHKJAMQ-UHFFFAOYSA-N 0.000 description 3
- DUCLMCMBTHOIAI-UHFFFAOYSA-N 2-(4-chlorophenoxy)propyl methanesulfonate Chemical compound CS(=O)(=O)OCC(C)OC1=CC=C(Cl)C=C1 DUCLMCMBTHOIAI-UHFFFAOYSA-N 0.000 description 3
- JCJQCLUMVBDDAQ-UHFFFAOYSA-N 2-[2-(4-chlorophenoxy)propoxy]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1OCC(C)OC1=CC=C(Cl)C=C1 JCJQCLUMVBDDAQ-UHFFFAOYSA-N 0.000 description 3
- -1 4-chloro-phenoxy Chemical group 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 102000000452 Acetyl-CoA carboxylase Human genes 0.000 description 3
- 108010016219 Acetyl-CoA carboxylase Proteins 0.000 description 3
- 108010018763 Biotin carboxylase Proteins 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 244000304962 green bristle grass Species 0.000 description 3
- FLZBNHIVFKVMQN-UHFFFAOYSA-N o-[2-(4-chlorophenoxy)propyl]hydroxylamine Chemical compound NOCC(C)OC1=CC=C(Cl)C=C1 FLZBNHIVFKVMQN-UHFFFAOYSA-N 0.000 description 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- XMRTVWAOAZXLHM-UHFFFAOYSA-N methyl 2-(4-chlorophenoxy)propanoate Chemical compound COC(=O)C(C)OC1=CC=C(Cl)C=C1 XMRTVWAOAZXLHM-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012053 oil suspension Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 1
- 241000209764 Avena fatua Species 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 241000722731 Carex Species 0.000 description 1
- 240000004585 Dactylis glomerata Species 0.000 description 1
- 241000209049 Poa pratensis Species 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 208000006278 hypochromic anemia Diseases 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000008654 plant damage Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/46—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms
- C07C323/47—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms to oxygen atoms
-
- 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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
- A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
-
- 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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention provides application of cyclohexane-1, 3-diketone compound as herbicide, wherein the structural formula of the cyclohexane-1, 3-diketone compound is shown in the specification
Description
Technical Field
The invention relates to the field of herbicides, and in particular relates to a new application of cyclohexane-1, 3-diketone compounds.
Background
Cyclohexane-1, 3-dione herbicides are a very important group of herbicides, which were first developed in the 60's of the 20 th century to eliminate weeds by inhibiting acetyl-coa carboxylase (ACCase) and disrupting fatty acid biosynthesis. The herbicide is a high-efficiency, safe and high-selectivity ACCase inhibitor, has special effects only on most annual and perennial grassy weeds, and is safe to dicotyledonous crops, and therefore, much effort is devoted to the development of the herbicide.
Disclosure of Invention
In view of the above, it is necessary to provide a use of cyclohexane-1, 3-dione compounds as herbicides.
Specifically, the invention provides application of cyclohexane-1, 3-diketone compound as herbicide, wherein the structural formula of the cyclohexane-1, 3-diketone compound is shown in the specification
The herbicide is used for preventing and controlling weeds in soybean fields.
Wherein the weeds in the soybean field comprise barnyard grass, wild oat, crab grass, green bristlegrass herb, bluegrass, alopecurus, stiff grass and the like.
Detailed Description
The technical solution of the present invention is further described in detail by the following embodiments.
Example 1
This example provides a compound e 1: 2- {1- [2- (4-chloro-phenoxy) -propoxyiimino ] -propyl } -5- (2-ethylsulfanyl-propyl) -3-hydroxy-cyclohex-2-enone of the formula:
the synthesis method of the compound comprises the following steps:
first, synthesis of 2- (toluene-4-sulfonic acid) -propionic acid methyl ester:
adding 10.4g of methyl lactate, 0.36g of DMAP and 19g of p-toluenesulfonyl chloride into a reactor, dissolving with toluene, maintaining the temperature at 0 ℃, then dripping 10.1g of triethylamine into the reaction system, heating to 50 ℃ after dripping, and keeping the temperature for 1 h; after completion of the reaction, insoluble matter was removed by filtration, and the filtrate was extracted with acid water, and the organic layer was taken to remove the solvent to obtain 24.5g of methyl 2- (toluene-4-sulfonate) -propionate.
Second, synthesis of 2- (4-chloro-phenoxy) -propionic acid methyl ester:
24.5g of methyl 2- (toluene-4-sulfonate) -propionate, 14.7g of p-chlorophenol and 8.5g of sodium bicarbonate were charged into a reactor, and the mixture was dissolved in toluene, reacted at 60 ℃ under reduced pressure for 3 hours, after the reaction was completed, insoluble matter was removed by centrifugation, and acid water was added to the filtrate to extract the mixture, and the solvent was removed from the organic layer to obtain 18.6g of methyl 2- (4-chloro-phenoxy) -propionate.
Step three, synthesizing 2- (4-chlorophenoxy) -propanol:
adding 18.6g of 2- (4-chloro-phenoxy) -methyl propionate, 7.7g of calcium chloride and 6.6g of sodium borohydride into a reactor, dissolving the mixture by using ethanol, heating the mixture to 30 ℃, keeping the temperature for 5 hours, adding a sulfuric acid aqueous solution into a reaction system after the reaction is finished, removing the solvent, adding water and toluene, collecting an organic layer, and removing the solvent to obtain 15.8g of 2- (4-chlorophenoxy) -propanol.
Step four, synthesizing methanesulfonic acid 2- (4-chloro-phenoxy) -propyl ester:
adding 15.8g of 2- (4-chlorophenoxy) -propanol into a reactor, dissolving with toluene, dropwise adding 12.9g of triethylamine into the reaction system, dropwise adding 9.7g of methylsulfonyl chloride at 10 ℃, keeping the temperature at 10 ℃ for 3h after the dropwise adding is finished, filtering or centrifuging to remove insoluble substances after the reaction is finished, adding acid water into the filtrate for extraction, taking an organic layer, and removing the solvent to obtain 21.9g of methanesulfonic acid 2- (4-chloro-phenoxy) -propyl ester.
Step five, synthesizing 2- [2- (4-chloro-phenoxy) -propoxy]-isoindole-1, 3-dione:
21.9g of 2- (4-chloro-phenoxy) -propyl methanesulfonate, 20.3g N-hydroxyphthalimide, and 3.8g of sodium hydrogencarbonate were charged into a reactor, dissolved in DMF, reacted at 90 ℃ for 4 hours, after removal of the solvent, water and toluene were added, and the organic layer was collected and the solvent was removed to give 24.8g of 2- [2- (4-chloro-phenoxy) -propoxy ] -isoindol-1, 3-dione.
Sixthly, synthesizing O- [2- (4-chloro-phenoxy) -propyl]-hydroxylamine:
24.8g of 2- [2- (4-chloro-phenoxy) -propoxy ] -isoindole-1, 3-dione is added to the reactor, dissolved with dichloromethane, and then 8.4g of hydrazine hydrate is added dropwise, after the addition, the reaction is carried out at 40 ℃ for 1 hour, after the reaction is finished, water is added for extraction, and an organic layer is collected and the solvent is removed to obtain 14.8g O- [2- (4-chloro-phenoxy) -propyl ] -hydroxylamine.
Seventh step, compound e1 was synthesized: 2- {1- [2- (4-chloro-phenoxy) -propoxyiimino ] -propyl } -5- (2-ethylsulfanyl-propyl) -3-hydroxy-cyclohex-2-enone
14.8g 14.8g O- [2- (4-chloro-phenoxy) -propyl ] -hydroxylamine and 19g propionyltrione were added to the reactor, dissolved in methanol, followed by addition of 0.1g acetic acid, reaction at 80 ℃ for 2h, removal of the solvent after the reaction was complete, and drying with water gave 31g pure compound e1 as a reddish brown viscous liquid with a yield of 71%.
The result of nuclear magnetic detection of the target product compound e1 obtained in this step is: 1HNMR (400MHz CDCl)3) δ 7.2(2H, m), δ 6.8(2H, m), δ 04.6(1H, q), δ 14.1(2H, d), δ 2.8(2H, q), δ 2.5(2H, q), δ 2.2(2H, m), δ 2.1(1H, m), δ 1.5(2H, m), δ 1.2(11H, m), δ 1.1(3H, t), δ 0.9(1H, m). therefore, it can be judged that the structural formula of the objective compound e1 is as shown above.
Application verification
Oil suspension with effective mass of 25%: active substance, 10% sodium dodecyl sulphate, 65% mineral oil, wherein the active substance is compound e1 as provided in example 1.
The seeds of soybean, barnyard grass, wild oat, crab grass, green bristlegrass herb, blue grass, aloesbill and stiff grass are sown in standard soil in a plastic basin, cultured in an artificial climate chamber (temperature: 30 ℃, humidity: 30%), the oil suspension agent is sprayed in 3-5 leaf stages after seedling emergence, and the damage condition of plants is evaluated after 5-7 days, wherein the evaluation results are shown in the following table 1. Wherein the evaluation criteria of the plant damage condition are as follows:
5 ═ complete damage to plants;
4, has large influence on growth;
3, the growth influence is large;
2-mild inhibition or chlorosis;
1-a subtle symptom, local color change;
0-no damage to the plant.
TABLE 1 herbicidal effectiveness of the compounds e1
| Dosage of the preparation | Soybean | Barnyard grass | Wild oat | Tang style food | Herb of common Setaria | Poa pratensis | Wheat-looking bride | Hard grass |
| 15 g/mu e1 | 0 | 2 | 2 | 1 | 2 | 3 | 1 | 2 |
| 25 g/mu e1 | 0 | 4 | 5 | 4 | 5 | 5 | 3 | 4 |
| 40 g/mu e1 | 1 | 5 | 5 | 5 | 5 | 5 | 5 | 5 |
As can be seen from table 1: the cyclohexane-1, 3-dione compound provided by the embodiment of the invention generally has a good weed control effect, especially has a good control effect on weeds such as barnyard grass, wild oat, crab grass, green bristlegrass, bluegrass, alopecurus, and carex, which are widely generated in soybean fields, and has industrial and commercial application prospects.
Finally, it should be noted that: the above examples are only intended to illustrate the technical solution of the present invention and not to limit it; although the present invention has been described in detail with reference to preferred embodiments, those skilled in the art will understand that: modifications to the specific embodiments of the invention or equivalent substitutions for parts of the technical features may be made; without departing from the spirit of the present invention, it is intended to cover all aspects of the invention as defined by the appended claims.
Claims (2)
1. The application of cyclohexane-1, 3-diketone compounds as herbicides is characterized in that: the structural formula of the cyclohexane-1, 3-diketone compound is shown in the specification
The herbicide is used for preventing and controlling weeds in soybean fields.
2. The application of cyclohexane-1, 3-diketone compounds as herbicides is characterized in that: the weeds in the soybean field are barnyard grass, wild oat, crab grass, green bristlegrass herb, blue grass, aloesvarum or stiff grass.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202111332014.XA CN113973824A (en) | 2020-01-16 | 2020-01-16 | Use of cyclohexane-1, 3-diones as herbicides |
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| CN202010044702.5A CN111205208B (en) | 2020-01-16 | 2020-01-16 | Cyclohexane-1, 3-diketone compound and synthetic method and application thereof |
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| CN202010044702.5A Active CN111205208B (en) | 2020-01-16 | 2020-01-16 | Cyclohexane-1, 3-diketone compound and synthetic method and application thereof |
| CN202111332014.XA Pending CN113973824A (en) | 2020-01-16 | 2020-01-16 | Use of cyclohexane-1, 3-diones as herbicides |
| CN202111396455.6A Pending CN113979907A (en) | 2020-01-16 | 2020-01-16 | Cyclohexane-1, 3-dione compound and application thereof |
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| CN114105842A (en) * | 2020-08-28 | 2022-03-01 | 郑州手性药物研究院有限公司 | Cyclohexadiene oxime ether compound and application thereof |
| CN112568221B (en) * | 2020-12-04 | 2022-09-16 | 郑州手性药物研究院有限公司 | Synergistic adjuvant for agricultural chemicals in rice field and its application |
| CN115417791B (en) * | 2022-09-23 | 2023-10-27 | 郑州手性药物研究院有限公司 | Oxime ether 1, 3-cyclohexanedione compound and synthetic method and application thereof |
| CN117882729A (en) * | 2022-11-21 | 2024-04-16 | 郑州手性药物研究院有限公司 | Herbicide composition containing cyclohexane-1, 3-dione derivative and application thereof |
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| CN111205208B (en) | 2021-12-17 |
| CN113979907A (en) | 2022-01-28 |
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