WO2023020274A1 - 一种3-异恶唑烷酮类化合物及其制备方法、除草组合物和应用 - Google Patents
一种3-异恶唑烷酮类化合物及其制备方法、除草组合物和应用 Download PDFInfo
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- WO2023020274A1 WO2023020274A1 PCT/CN2022/109677 CN2022109677W WO2023020274A1 WO 2023020274 A1 WO2023020274 A1 WO 2023020274A1 CN 2022109677 W CN2022109677 W CN 2022109677W WO 2023020274 A1 WO2023020274 A1 WO 2023020274A1
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- isoxazolidinone
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- 150000004867 thiadiazoles Chemical class 0.000 description 1
- GLDAZAQRGCSFNP-UHFFFAOYSA-N thiencarbazone Chemical compound O=C1N(C)C(OC)=NN1C(=O)NS(=O)(=O)C1=C(C)SC=C1C(O)=O GLDAZAQRGCSFNP-UHFFFAOYSA-N 0.000 description 1
- XSKZXGDFSCCXQX-UHFFFAOYSA-N thiencarbazone-methyl Chemical compound COC(=O)C1=CSC(C)=C1S(=O)(=O)NC(=O)N1C(=O)N(C)C(OC)=N1 XSKZXGDFSCCXQX-UHFFFAOYSA-N 0.000 description 1
- LOQQVLXUKHKNIA-UHFFFAOYSA-N thifensulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C2=C(SC=C2)C(O)=O)=N1 LOQQVLXUKHKNIA-UHFFFAOYSA-N 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 108020002982 thioesterase Proteins 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical compound BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical compound C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
- 230000009105 vegetative growth Effects 0.000 description 1
- 150000004669 very long chain fatty acids Chemical class 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
Definitions
- the invention belongs to the technical field of pesticides, and in particular relates to a 3-isoxazolidinone compound, a preparation method thereof, a herbicidal composition and application thereof.
- the present invention provides a kind of 3-isoxazolidinone compound and its preparation method, herbicidal composition and application, said compound maintains comparable or even better herbicidal activity Basically, it has better crop safety and can establish better selectivity on crops; moreover, the compound of the present invention has better anti-volatility and is not easy to drift.
- Q 1 and Q 2 independently represent O or S;
- R 1 and R 2 each independently represent an alkyl group, preferably a C1-C8 alkyl group, more preferably a C1-C6 alkyl group.
- Q 1 and Q 2 independently represent O; R 1 and R 2 independently represent methyl (ie compound 1).
- the alkyl group with more than two carbon atoms can be straight chain or branched chain.
- Alkyl groups are, for example, C1 alkyl-methyl; C2 alkyl-ethyl; C3 alkyl-propyl such as n-propyl or isopropyl; C4 alkyl-butyl such as n-butyl, isobutyl C5 alkyl-pentyl such as n-pentyl; C6 alkyl-hexyl such as n-hexyl, isohexyl and 1,3-dimethylbutyl.
- Halogen is fluorine, chlorine, bromine or iodine.
- the present invention also provides a preparation method of the 3-isoxazolidinone compound, comprising the following steps:
- Hal represents halogen, preferably bromine.
- said step is carried out in the presence of a base and a solvent.
- the base is selected from inorganic bases (such as K 2 CO 3 , Na 2 CO 3 , Cs 2 CO 3 , NaHCO 3 , KF, CsF, KOAc, AcONa, K 3 PO 4 , t-BuONa, EtONa, NaOH, KOH, NaOMe, etc.) or at least one of organic bases (such as pyrazole, triethylamine, DIEA, etc.).
- inorganic bases such as K 2 CO 3 , Na 2 CO 3 , Cs 2 CO 3 , NaHCO 3 , KF, CsF, KOAc, AcONa, K 3 PO 4 , t-BuONa, EtONa, NaOH, KOH, NaOMe, etc.
- organic bases such as pyrazole, triethylamine, DIEA, etc.
- the solvent is selected from at least one of DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane, toluene or ethyl acetate.
- the present invention also provides a herbicidal composition, which comprises (i) a herbicidally effective amount of at least one of the above-mentioned 3-isoxazolidinone compounds.
- the herbicidal composition further comprises (ii) one or more herbicidally effective amounts of additional herbicides and/or safeners.
- the herbicidal composition further includes (iii) an agrochemically acceptable formulation adjuvant.
- the present invention also provides a method for controlling undesired plants, comprising applying a herbicidally effective amount of at least one of said 3-isoxazolidinone compounds or said herbicidal composition to plants or their locus or applied to soil or water bodies to control unwanted plant emergence or growth.
- said unwanted vegetation comprises herbicide resistant or tolerant weed species.
- the present invention also provides the use of at least one of said 3-isoxazolidinone compounds or said herbicidal composition for controlling undesired plants.
- said 3-isoxazolidinones are used for controlling weeds in useful crops.
- the useful crops include transgenic crops or crops treated with genome editing technology, and the weeds include herbicide-resistant or tolerant weed species.
- the compounds of the formula I according to the invention have outstanding herbicidal activity against many economically important monocotyledonous and dicotyledonous harmful plants.
- the active substances according to the invention are also effective against perennial weeds which grow from rhizomes, rhizomes or other perennial organs and are difficult to control. In this context, it is generally immaterial whether the substance is applied before sowing, before germination or after germination.
- Representative examples of groups of monocotyledonous and dicotyledonous weeds that can be controlled by the compounds of the present invention are specifically mentioned, without limitation to a defined species.
- weed species on which the active substances are effective include monocots: annuals Avena, rye, Grass, Aleuria, Fararis, barnyardgrass, crabgrass, Setaria and Cyperus, and perennial icegrass Grass, Bermudagrass, Imperata and Sorghum, and perennial Cyperus.
- dicotyledonous weed species With regard to dicotyledonous weed species, its effect can be extended to species such as annual pleura, Viola, Possina, Sesame, Chickweed, Amaranthus, S. Genus, Matricaria, and Abutilus, and the perennial weeds Convolvuum, Thistle, Rumex, and Artemisia.
- the active substance of the present invention is effective in controlling harmful plants such as Barnyardgrass, Sagittarius, Alisma, Eleocharis, Canegrass and Cyperus under undetermined conditions of rice sowing.
- the compounds of the present invention have particularly good activity against the following plants: Apira weed, Sesame ono, Polygonum curcuma, Chickweed, Ivy leaf pombe, Arabian pansy, pansy and amaranth, chrysoprase and Kochia .
- the compounds of the present invention have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, they are not effective against economically important crop plants such as peanut, wheat, barley, rye, rice, corn, sugar beet, cotton and soybean. No damage, or the damage is negligible. In particular it is well compatible with cereal crops such as wheat, barley and corn, especially wheat.
- the compounds according to the invention are therefore very suitable for the selective control of unwanted plants in agricultural crops or ornamental plants.
- Transgenic plants Due to their herbicidal properties, these active substances can be used to control harmful plants in known or upcoming genetically engineered plant cultivation.
- Transgenic plants often have superior traits, such as resistance to specific insecticides, especially herbicides, resistance to plant diseases or plant disease-causing microorganisms, such as specific insects or fungal, bacterial or viral microorganisms.
- Other specific properties are related to the following conditions of the product, for example, quantity, quality, storage stability, composition and special ingredients. Thus, it is known to obtain transgenic plant products with increased starch content or improved starch quality or different fatty acid composition.
- the compounds of formula I according to the invention or their salts are preferably used in economically important transgenic crops and ornamental plants, such as cereals, such as wheat, barley, rye, oats, millet, rice, cassava and corn, or in sugar beets, Cultivation of cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetable plants.
- the compounds of the formula I are preferably used as herbicides in the cultivation of useful plants which are resistant or which have been genetically engineered to be resistant to the toxic action of the herbicides.
- glufosinate herbicides e.g. EP-0242236 A, EP-0242246 A
- glyphosate herbicides WO 92/00377
- sulphur Urea herbicides EP-0257993 A, US-5013659 A
- Plant cells with reduced activity gene products can be prepared, for example, by expressing at least one appropriate antisense-RNA, sense-RNA to achieve co-suppression, or by expressing at least one appropriately constructed ribozyme, It specifically cleaves the transcripts of the above mentioned gene products.
- DNA molecules that contain the entire coding sequence of the gene product including any flanking sequences that may be present, and to use DNA molecules that contain only a portion of the coding sequence, which must be long enough to achieve antisense in cells. Effect. Sequences with a high degree of homology, but not complete identity, to gene product coding sequences may also be used.
- the synthesized protein When expressing nucleic acid molecules in plants, the synthesized protein can be localized in any desired plant cell compartment. However, for localization in a specific compartment, it is possible, for example, to link the coding region and the DNA sequence to ensure localization at a specific position. These sequences are known to those skilled in the art (see, e.g., Braun et al., EMBO J. 11 (1992) 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al. Plant J. 1 (1991), 95-106).
- Transgenic plant cells can be recombined into whole plants using known techniques.
- the active substances according to the invention are used on transgenic crops, in addition to the effect of inhibiting harmful plants that can be observed on other crops, there will often be special effects on the corresponding transgenic crops, for example, the control can be improved or expanded.
- the present invention therefore also provides the use of said compounds as herbicides for controlling harmful plants in transgenic crop plants.
- the compounds according to the invention can significantly regulate the growth of crop plants. These compounds are used for targeted control of plant components and to facilitate harvesting, such as desiccation and dwarf growth of plants, by modulating the metabolism involved in the plant. Moreover, they are also suitable for regulating and suppressing undesired vegetative growth without destroying the growth of the crop. Inhibition of plant growth plays a very important role in many monocot and dicot crops, as lodging can be reduced or completely prevented.
- the compounds of the invention can be applied using conventional formulations, wettable powders, concentrated emulsions, sprayable solutions, powders or granules.
- the present invention also provides herbicidal compositions comprising a compound of formula I.
- the compounds of formula I can be formulated in various ways. Examples of suitable formulation options are: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, concentrated emulsions (EC), e.g.
- oil-in-water and water-in-oil emulsions sprayable solutions, suspension concentrates (SC), dispersible oil suspensions (OD), suspensions in oil or water as diluents, oil-miscible solutions, powders (DP), capsule suspensions (CS ), seeddressing compositions, granules for broadcasting and soil application, spray granules, coated granules and absorbent granules, water dispersible granules (WG), water soluble granules (SG), ULV (ultra low volume) formulations, microcapsules and wax products.
- Necessary formulation auxiliaries such as inert substances, surfactants, solvents and other additives are likewise known and described in, for example, Watkins' Handbook of Powder Diluent Insecticides and Carriers, 2nd Edition, Darland Books, Caldwell NJ; Hv01phen "An Introduction to the Chemistry of Clay Colloids", 2nd ed., J. Wiley and Sons, NY; C.
- Wettable powders are uniformly dispersible in water and, in addition to active substances, also include diluents or inert substances, ionic and nonionic surfactants (wetting agents, dispersants), such as polyethoxylated alkylphenols, polyethoxylated Ethoxylated fatty alcohol, polyoxyethylated fatty amine, fatty alcohol polyglycol ether sulfate, alkylsulfonate, alkylphenylsulfonate, sodium lignosulfonate, 2,2'-dinaphthyl methane - Sodium 6,6'-disulfonate, sodium dibutylnaphthalenesulfonate or sodium oleoylmethyl taurate.
- the herbicide active substances are ground finely, for example using customary apparatus, for example with hammer mills, fan mills and jet mills, and the adjuvants are mixed simultaneously or sequentially.
- Concentrated emulsions are prepared by dissolving the active substance in an organic solvent such as butanol, cyclohexanone, dimethylformamide, xylene or a mixture of higher boiling aromatic compounds or hydrocarbons or solvents, and adding a One or more ionic and/or nonionic surfactants (emulsifiers).
- organic solvent such as butanol, cyclohexanone, dimethylformamide, xylene or a mixture of higher boiling aromatic compounds or hydrocarbons or solvents.
- emulsifiers examples include calcium alkylarylsulfonates such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohols Polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters, or polyoxyethylene sorbitan esters such as polyoxyethylene sorbitan fatty esters polysaccharide ester.
- calcium alkylarylsulfonates such as calcium dodecylbenzenesulfonate
- nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohols Polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as sorbitan fatty acid
- Powders are obtained by grinding the active substance with finely divided solid substances such as talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
- Water- or oil-based suspensions may be prepared, for example, by wet grinding using a commercially available bead mill, with or without the addition of surfactants of the other formulation type described above.
- Emulsions such as oil-in-water emulsifiers (EW) can be prepared using aqueous organic solvents using stirrers, colloid mills and/or static mixers, adding, if desired, surfactants of another formulation type as described above.
- EW oil-in-water emulsifiers
- Granules are prepared by spraying the active substance onto the adsorbate, granulating with an inert material, or concentrating the active substance on the surface of a carrier such as sand, kaolinite, granulating the inert material through a binder, sticking Mixtures such as polyvinyl alcohol, sodium polyacrylate or mineral oil. Suitable active substances can be granulated, if desired mixed with fertilizers, in the same way as fertilizer granules. Aqueous suspension granules are prepared using the usual methods, such as spray-drying, fluidized bed granulation, pan granulation, mixing with a high-speed mixer, and extrusion without solid inert materials.
- the agrochemical formulations generally comprise from 0.1 to 99%, in particular from 0.1 to 95%, by weight of active substances of the formula I.
- the active substance concentration in the wettable powders is, for example, from about 10 to 99% by weight, the usual formulation components constituting the remainder to 100% by weight.
- the concentration of active substance in the concentrated emulsions may be from about 1 to 90%, preferably from 5 to 80%, by weight.
- Powder formulations contain 1 to 30% by weight active substance, usually preferably 5 to 20% by weight active substance, whereas sprayable solutions contain approximately 0.05 to 80% by weight, preferably 2 to 50% active substance .
- the content of the active substance in the water-suspended granule mainly depends on whether the active substance is liquid or solid, and the additives, fillers, etc. used in granulation.
- the active substance content of the aqueous granules is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
- the formulation of active substances may include tackifiers, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents, solvents, fillers, carriers, colorants, defoamers, evaporation inhibitors and Commonly used pH and viscosity modifiers in all cases.
- the mixing method can be For pre-mixed or bottled mixes.
- suitable active substances that can be mixed with the compound of formula I of the present invention are, for example, "World Pesticide New Variety Technical Encyclopedia", China Agricultural Science and Technology Press, 2010.9 and in the literature cited here known substances.
- the herbicide active substances mentioned below can be mixed with compound 1 (note: the name of the compound is either the common name according to the International Organization for Standardization (ISO), or the chemical name, with a code when appropriate):
- HPPD Hydrophenyl Pyruvate Dioxygenase inhibitors: including but not limited to the following types,
- Triketones for example, Sulcotrione (CAS NO: 99105-77-8); Mesotrione (Mesotrione, CAS NO: 104206-82-8); Bicyclopyrone (CAS NO : 352010-68-5); tembotrione (CAS NO: 335104-84-2); tefuryltrione (CAS NO: 473278-76-1); bicyclic sulcotrione (Benzobicyclon, CAS NO :156963-66-5);
- Diketonitriles for example, 2-cyano-3-cyclopropyl-1-(2-methylsulfonyl-4-trifluoromethylphenyl) propane-1,3-dione (CAS NO : 143701-75-1); 2-cyano-3-cyclopropyl-1-(2-methylsulfonyl-3,4-dichlorophenyl)propane-1,3-dione (CAS NO: 212829-55-5); 2-cyano-1-[4-(methylsulfonyl)-2-trifluoromethylphenyl]-3-(1-methylcyclopropyl)propane-1,3 - diketone (CAS NO: 143659-52-3);
- Isoxazoles for example, isoxaflutole (CAS NO: 141112-29-0); isoxachlortole (CAS NO: 141112-06-3); , CAS NO: 81777-89-1);
- Pyrazoles for example, topramezone (CAS NO: 210631-68-8); pyrasulfotole (CAS NO: 365400-11-9); pyrazoxazole (pyrazoxyfen, CAS NO: 71561-11-0); pyrazolate (CAS NO: 58011-68-0); benzofenap (CAS NO: 82692-44-2); -18-2); Tolpyralate (CAS NO: 1101132-67-5); Fenflurzone (CAS NO: 1992017-55-6); Cyclofluxazone (CAS NO: 1855929-45-1); Triazole sulfotrione (CAS NO: 1911613-97-2);
- EPSPS Enduvyl Shikimate Phosphate Synthase inhibitors: such as sulphosate, Glyphosate, glyphosate-isopropylammonium and glyphosate trimethylsulfonate ( glyphosate-trimesium);
- PPO Protoporphyrinogen Oxidase inhibitors: divided into pyrimidinediones, diphenyl-ethers, phenylpyrazoles, N-phenylimides , thiadiazoles, oxadiazoles, triazolones, oxazolidinediones and other herbicides with different chemical structures.
- pyrimidinedione herbicides include, but are not limited to, flumethazine (CAS NO: 134605-64-4), saflufenacil (CAS NO: 372137-35-4), Dimifluzalone (CAS NO: 158755-95-4), flumethiobacil (tiafenacil, CAS NO: 1220411-29-9), [3-[2-chloro-4-fluoro-5-(1 -Methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]ethyl acetate (Epyrifenacil, CAS NO: 353292-31-6), 1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl -3,4-dihydro-2H-benzo[1,4]oxazin-6-y
- Diphenyl ether herbicides include but are not limited to fomesafen (CAS NO: 72178-02-0), oxyfluorfen (CAS NO: 42874-03-3), aclofenfen (CAS NO: 74070-46-5), fluorinated milk ether (CAS NO: 131086-42-5), lactofen (CAS NO: 77501-63-4), methoxyben (CAS NO: 32861-85-1 ), acifluorfen (CAS NO: 1836-77-7), acifluorfen (CAS NO: 77501-90-7), acifluorfen or sodium salt (acifluorfen, CAS NO: 50594-66- 6 or 62476-59-9), carboxyfen (CAS NO: 42576-02-3), chlorofluorfen (CAS NO: 188634-90-4), fluoronitrofen (CAS NO: 13738-63-1) , furyloxyfen (CAS NO: 80020-41-3), nitrofluorfen (CAS NO: 4
- Phenylpyrazole herbicides include but not limited to metazachlor (CAS NO: 129630-19-9) and fluazolate (CAS NO: 174514-07-9);
- N-Phenyl imide herbicides include but not limited to Flumipropyn (CAS NO: 103361-09-7), Indoxafen (CAS NO: 142891-20-1), Flumipropyn (CAS NO: 84478-52-4) and fluoxalic acid (CAS NO: 87546-18-7);
- Thiadiazole herbicides include but are not limited to fluthiacet-methyl (fluthiacet-methyl, CAS NO: 117337-19-6), thiadiazole acid (CAS NO: 149253-65-6) and thiadiafen (CAS NO: 123249-43-4);
- Oxadiazole herbicides include but not limited to propargyl oxadiazone (CAS NO: 39807-15-3) and oxadiazon (CAS NO: 19666-30-9);
- Triazolinone herbicides include but not limited to carfentrazone (CAS NO: 128621-72-7), carfentrazone ethyl (CAS NO: 128639-02-1), sulfentrazone ( sulfentrazone, CAS NO: 122836-35-5), fentrazone (CAS NO: 68049-83-2) and bencarbazone (CAS NO: 173980-17-1);
- Oxazolidinedione herbicides include but not limited to cyclopentazone (CAS NO: 110956-75-7);
- herbicides include, but are not limited to, fenfenpyr (CAS NO: 158353-15-2), fluridazenzap (CAS NO: 188489-07-8), flufenacet (CAS NO: 190314-43-3 ), trifludimoxazin (CAS NO: 1258836-72-4), N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl- 1H-pyrazole-1-carboxamide (CAS NO: 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5- Methyl-1H-pyrazole-1-carboxamide (CAS NO: 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)- 5-Methyl-1H-pyrazole-1-carboxamide (CAS NO: 452099-05-7), N-tetrahydrofur
- ALS (Acetolactate Synthase) inhibitors include but not limited to the following herbicides or their mixtures:
- Sulfonylureas such as amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl Chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethyl Ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, formamide (foramsulfuron), halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl sodium salt -sodium), iofensulfuron, iofensulfuron sodium salt, mesosulfuron, metazosulfuron, met
- Imidazolinones such as imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin ( imazaquin) and imazethapyr;
- Triazolopyrimidine herbicides and sulfonanilides such as cloransulam, cloransulam-methyl, diclosulam, flumetsulam, diclosulam florasulam, metosulam, penoxsulam, pyroxsulam, pyrimisulfan, and triafamone;
- Pyrimidinyl benzoic acids such as bispyribac (bispyribac), bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl, pyrithiobenzoic acid ( pyrithiobac), pyrithiobac (pyrithiobac) sodium salt, 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid- 1-Methyl ethyl ester (CAS NO: 420138-41-6), 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino] -Propyl benzoate (CAS NO: 420138-40-5), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzylamine ( CAS NO: 420138
- Sulfonylaminocarbonyl-triazolinone herbicides such as flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone- sodium), thiencarbazone and thiencarbazone-methyl.
- ACCase (Acetyl CoA Carboxylas) inhibitors such as Fenthiaprop, alloxydim, alloxydim-sodium, butroxydim, methoxydim clethodim, clodinafop, clodinafop-propargyl, cyclooxydim, cyhalofop, cyhalofop-butyl, chloroform diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P Fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P Fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-methyl
- GS (Glutamine Synthetase) inhibitors such as Bialaphos/bilanafos, Bialaphos-natrium, Glufosinate-ammonium, Glufosinate-ammonium (Glufosinate) and refined glufosinate-ammonium (glufosinate-P);
- PDS Phytoene Desaturase inhibitors: such as flurochloridone, flurtamone, beflubutamid, norflurazon, fluridone , Diflufenican (Diflufenican), Picolinafen (Picolinafen), and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS NO: 180608-33-7);
- DHPS Dihydropteroate Synthase inhibitors: such as Asulam;
- DXPS Deoxy-D-Xyulose Phosphate Synthase inhibitors: such as Bixlozone and Clomazone;
- HST Homogentisate Solanesyltransferase inhibitors: such as Cyclopyrimorate
- SPS Solanesyl Diphosphate Synthase inhibitors: such as Aclonifen;
- Cellulose Synthesis inhibitors such as Indaziflam, Triaziflam, Chlorthiamid, Dichlobenil, Isoxaben, Flupoxam, 1-cyclohexyl-5-pentafluorophenoxy- 1 4 -[1,2,4,6]thiatriazin-3-ylamine (CAS NO: 175899-01-1) , and the azines disclosed in CN109688807A;
- VLCFAS Very Long-Chain Fatty Acid Synthesis inhibitors: including but not limited to the following types,
- Chloroacetamides such as acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, and dimethenamid-P ), metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, Propisochlor and thenylchlor;
- ⁇ -Oxyacetamides such as flufenacet (flufenacet) and mefenacet (mefenacet);
- ⁇ -Thioacetamides such as anilofos and piperophos
- Azolylcarboxamides such as cafenstrole, fentrazamide and ipfencarbazone;
- Benzofurans such as Benfuresate and Ethofumesate
- Isoxazolines such as fenoxasulfone and pyroxasulfone
- Thiocarbamate such as Cycloate, Dimepiperate, S-ethyldipropylthiocarbamate (EPTC), Esprocarb, molinate (Molinate), Orbencarb, Prosulfocarb, Thiobencarb/Benthiocarb, Triallate, Vernolate, and Formula II.1, II.2, II.3, II.4, II. 5.
- Isozoline compounds of II.6, II.7, II.8 and II.9, and those mentioned in patents such as WO 2006/024820, WO 2006/037945, WO 2007/071900 and WO 2007/096576 Other isoxazoline compounds.
- Fatty acid thioesterase inhibitors such as cycloheptafen Cinmethylin, Methiozolin;
- Serine threonine protein phosphatase (serine threonine protein phosphatase) inhibitors such as Endothall;
- Lycopene cyclase inhibitors such as Amitrole.
- Microtubule Assembly (Microtubule Assembly) inhibitors such as Benefin/benfluralin, Butralin, Dithiopyr, Thiazopyr, Ethalfluralin, Amprofur Prodiamine, Butamifos, Oryzalin, Pendimethalin, Chlorthaldimethyl/DCPA, DMPA Trifluralin, Propyzamide/pronamide, Dinitramine (CAS NO: 29091-05-2);
- Auxin Mimics such as 2,4,5 trichlorophenoxyacetic acid (2,4,5-T), 2,4-dichlorophenoxyacetic acid (2,4-D ), 2,4-dichlorophenoxybutyric acid (2,4-DB), 3,4-dichlorophenoxybutyric acid (3,4-DB), 2,4-DEB (CAS NO: 94-83 -7), 4-chlorophenoxyacetic acid (4-CPA), 4-CPP (CAS NO: 3307-39-9), cloprop (CAS NO: 101-10-0), clofop (CAS NO: 26129- 32-8), Clomeprop, Dichlorprop, 2,4-Dichlorprop, 2-methyl-4-chlorobutyric acid (MCPB), 2-methyl-4-chloropropionic acid (Mecoprop), Chloroprop Aminopyralid, Clopyralid, Aminocyclopyrachlor, Florpyraxifen, Halauxifen, Quinclorac, Benazolin-ethyl, Piclor
- D1 Serine 264 binders (and other non-histidine 215 binders) (D1 Serine 264 binders (and other non-histidine 215 binders)): such as Ametryne, Atrazine, Cyanazine, Dimethametryn, Prometon, Prometryne, Propazine, Simazine, Terbutylazine, Terbutryne, Chlorotoluron, Diuron, Fluometuron, Iso Isoproturon, Linuron, Metobromuron, Methabenz thiazuron (CAS NO: 18691-97-9), Monuron, Tebuthiuron, Hexazinone, Metamitron, Metribuzin , Bromacil, Lenacil, Terbacil, Chloridazon/pyrazon, Amicarbazone, Desmedipham, Phenmedipham, Chloranocryl/dicryl, CAS NO: 2164- 09-2), propanil, chlorazine (CAS NO:
- D1 Histidine 215 binders such as Bromoxynil, Ioxynil, Pyridate, Bentazon;
- Auxin Transport inhibitors such as Diflufenzopyr (CAS NO: 109293-97-2), Naptalam;
- PS l Electron Diversion such as Diquat, Paraquat
- Uncouplers such as Dinoseb, 4,6-dinitro-o-cresol (DNOC);
- another herbicide (component B) mixed with compound 1 (component A) is selected from one or more than two of the following compounds: mesotrione (CAS number: 104206 -82-8), Furosulcotrione (CAS No.: 473278-76-1), Bicyclic Sulfotrione (CAS No.: 156963-66-5), Bifentrazone (CAS No.: 1622908-18-2) , Cycloflumetrione (CAS No.: 1855929-45-1), Triazole Sulfotrione (CAS No.: 1911613-97-2), Fenzaflurone (CAS No.: 1992017-55-6), fenquinotrione (CAS number: 1342891-70-6), (CAS No.: 2421252-30-2), Isoxaflutole (CAS No.: 141112-29-0), Fluoxazone (CAS No.: 61213-25-0), Diflufenamide (CAS No.
- Epyrifenacil (CAS No.: 353292-31-6), (CAS number: 2669821-71-8), (CAS No.: 2669111-66-2), bemiconazole (CAS No.: 1949837-17-5), atrazine (CAS No.: 1912-24-9), promezazin (CAS No.: 7287-19 -6), sigrazine (CAS No.: 1014-70-6), terbuthylazine (CAS No.: 5915-41-3), terbufen (CAS No.: 886-50-0), ametrazine ( CAS No.: 834-12-8), mecitrione (CAS No.: 21087-64-9), amfentrazone (CAS No.: 129909-90-6), chlorotoluron (CAS No.: 15545-48- 9), isoproturon (CAS number: 34123-59-6), diuron (CAS number: 330-54-1), propanil (CAS number: 709-98-8), bentazone (CAS
- the weight ratio of active ingredients A and B in the herbicidal composition is 1:1000 ⁇ 1000:1, 1:800 ⁇ 800:1, 1:600 ⁇ 600:1, 1:500 ⁇ 500:1, 1:500 ⁇ 500:1, 1 :400 ⁇ 400:1, 1:300 ⁇ 300:1, 1:200 ⁇ 200:1, 1:180 ⁇ 180:1, 1:150 ⁇ 150:1, 1:120 ⁇ 120:1, 1:100 ⁇ 100:1, 1:80 ⁇ 80:1, 1:50 ⁇ 50:1, 1:30 ⁇ 30:1, 1:20 ⁇ 20:1, 1:10 ⁇ 10:1, 1:5 ⁇ 1 :1 or 1:1 ⁇ 5:1.
- the mass percent content of A and B in the herbicidal composition accounts for 1-95% of the total, preferably 10-80%.
- a herbicidal compound as described herein that can be used in the context of the present invention is capable of forming geometric isomers such as E/Z isomers, it is possible to use both, pure Isomers and mixtures thereof. If a herbicidal compound as described herein has one or more chiral centers and thus exists as enantiomers or diastereomers, it is possible to use both, the pure enantiomers, in the compositions according to the invention Enantiomers and diastereomers and mixtures thereof. If the herbicidal compounds as described herein have ionizable functional groups, they can also be used in the form of their agriculturally acceptable salts.
- the salts of those cations and the acid addition salts of those acids are suitable, the cations and anions of which, respectively, have no adverse effect on the activity of the active compounds.
- Preferred cations are ions of alkali metals, preferably lithium, sodium and potassium, alkaline earth metals, preferably calcium and magnesium, and transition metals, preferably manganese, copper, zinc and iron, further ammonium and substituted Ammonium of which 1 to 4 hydrogen atoms are replaced by C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl , hydroxy-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, phenyl or benzyl substituted, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium Ammonium, trimethyl
- the anions of available acid addition salts are mainly chloride ion, bromide ion, fluoride ion, iodide ion, hydrogen sulfate, methyl sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, bicarbonate, carbonic acid , hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of C 1 -C 4 -alkanoic acids, preferably formate, acetate, propionate and butyrate.
- the herbicidal compounds having a carboxyl group as described herein may be used in acid form, in the agriculturally suitable salts mentioned above or otherwise in the form of agriculturally acceptable derivatives, for example as amides such as mono- and di-C 1 -C 6 -Alkyl amides or aryl amides, as esters such as allyl esters, propargyl esters, C 1 -C 10 -alkyl esters, alkoxyalkyl esters, tefuryl ((tetrahydrofuran-2-yl) Methyl) esters and also as thioesters, for example as C 1 -C 10 -alkylthioesters.
- amides such as mono- and di-C 1 -C 6 -Alkyl amides or aryl amides
- esters such as allyl esters, propargyl esters, C 1 -C 10 -alkyl esters, alkoxyalkyl esters,
- Preferred mono- and di-C 1 -C 6 -alkylamides are methyl and dimethylamide.
- Preferred arylamides are, for example, anilide and 2-chloroanilide.
- Preferred alkyl esters are for example methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1-methylhexyl), meptyl (1-methylheptyl), heptyl 2-ethylhexyl, octyl or isooctyl (2-ethylhexyl) ester.
- C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl esters are linear or branched C 1 -C 4 -alkoxyethyl esters, such as 2-methoxyethyl ester, 2- Ethoxyethyl ester, 2-butoxyethyl (butotyl) ester, 2-butoxypropyl ester or 3-butoxypropyl ester.
- An example of a straight-chain or branched C 1 -C 10 -alkylthioester is ethylthioester.
- the commercially available formulations are, if necessary, diluted in the usual manner, for example with water in the case of wettable powders, concentrated emulsions, suspensions and granules suspended in water. Powders, granules for soil application or solutions for broadcasting and spraying generally do not require further dilution with inert substances before use.
- the amount of the compound of formula I required to be used varies with external conditions such as temperature, humidity, the nature of the herbicide used, and the like. It can vary widely, for example between 0.001 and 1.0 kg a.i./ha, or more active material, but preferably between 0.005 and 750 ga.i./ha.
- compound 1-1 (284mg, 1.0mmol, 1.0eq.) was dissolved in 10mL acetonitrile, then compound 1-2 (115mg, 1.0mmol, 1.0eq.), K 2 CO 3 (207mg, 1.5mmol, 1.5eq.), the reaction solution was heated to 50°C and reacted at this temperature for 1h. After the reaction was completed, it was quenched with water, extracted with ethyl acetate, dried over anhydrous sodium sulfate, filtered, concentrated, and column chromatographed to obtain the target product 1 (232.5 mg, white solid, 73% yield).
- the activity level criteria for plant destruction i.e. growth control rate are as follows:
- Level 5 The growth control rate is above 85%;
- Level 4 The growth control rate is greater than or equal to 60% and less than 85%;
- Level 3 The growth control rate is greater than or equal to 40% and less than 60%;
- Level 2 The growth control rate is greater than or equal to 20% and less than 40%;
- Level 1 The growth control rate is greater than or equal to 5% and less than 20%;
- Grade 0 The growth control rate is less than 5%.
- the above growth control rate is the fresh weight control rate.
- the monocotyledonous and dicotyledonous weed seeds (Artemisia sativa, shepherd's purse, velvet hemp, pig scorpion, chickweed, Maijiagong, sage, kannada, Japanese kannada, goosegrass, sage, hard Grass, candlegrass, mother-in-law, brome, knotweed, amaranthus, amaranthus, quinoa, commelina, endive, field bindweed, spiny cabbage, nightshade, iron amaranth, crabgrass, barnyardgrass Grass, green foxtail, golden foxtail, daughter of a daughter, bermudagrass, sagittarius, firefly, Cyperus cyperus, broken rice sedge, special-shaped sedge, fluttering grass, purslane, cocklebur, morning glory, liquor grass, etc.) And the main crop seeds (wheat, corn, rice, soybean, cotton, rapeseed, millet, sorghum,
- Control compound A (clomazone dichloride); control compound B: clomazone.
- the compound of the present invention has better crop safety than commercialized clomazone and diclomazone, especially safer for wheat and rice, and is more effective in crabgrass It has comparable or even better herbicidal activity on key weeds such as , Stephania chinensis, Abutilus velvet, and Japanese kangaroo, and can establish better selectivity on crops.
- the activity level criteria for plant destruction i.e. growth control rate are as follows:
- Level 8 The growth control rate is greater than or equal to 80% and less than 100%
- Level 7 The growth control rate is greater than or equal to 70% and less than 80%;
- Level 6 The growth control rate is greater than or equal to 60% and less than 70%
- Level 5 The growth control rate is greater than or equal to 50% and less than 60%;
- Level 4 The growth control rate is greater than or equal to 40% and less than 50%;
- Level 3 The growth control rate is greater than or equal to 30% and less than 40%;
- Level 2 The growth control rate is greater than or equal to 15% and less than 30%;
- Level 1 The growth control rate is greater than 0% and less than 15%;
- the above growth control rate is the fresh weight control rate.
- the monocotyledonous and dicotyledonous weed seeds (Artemisia sativa, shepherd's purse, velvet hemp, pig scorpion, chickweed, Maijiagong, sage, kannada, Japanese kannada, goosegrass, sage, hard Grass, candlegrass, mother-in-law, brome, knotweed, amaranthus, amaranthus, quinoa, commelina, endive, field bindweed, spiny cabbage, nightshade, iron amaranth, crabgrass, barnyardgrass Grass, green foxtail, golden foxtail, daughter of a daughter, bermudagrass, sagittarius, firefly, Cyperus cyperus, broken rice sedge, special-shaped sedge, fluttering grass, purslane, cocklebur, morning glory, liquor grass, etc.) And the main crop seeds (wheat, corn, rice, soybean, cotton, rapeseed, millet, sorghum,
- the compound of the present invention has better soil sealing safety compared with commercial clomazone and diclomazone, and can maintain comparable or even better herbicidal activity, especially for ryegrass
- Chickweed is very sensitive to clomazone-like compounds and is a good indicator of the volatility of bleaching compounds.
- Untreated control plates, clomazone emulsifiable concentrate, and clomazone diclomazone emulsifiable concentrate formulations were included in each test. These formulations are the reference standards for the experimental formulations for comparison.
- the 4 inch plastic canisters were fitted with a paper basket coffee filter cut to size that was placed in the bottom of each canister to cover the drain hole and prevent soil from draining from the bottom of the canister.
- Each pot was filled with sandy loam soil sifted through a #10 mesh screen (to remove large soil particles and debris). Fill soil pots and water lightly before applying the treatment.
- the test solutions were applied to the soil surface with a sprayer, and each test solution was repeated 2 times at a rate of 0.25 kg a.i./ha.
- Each replicate test was assembled by placing an empty 4 inch plastic jar on top of the greenhouse.
- the cans contained mature chickweed, approximately 2 inches in height, placed around each empty can in an 8-spoke pattern.
- 4 cans of mature chickweed were placed at the 3, 6, 9 and 12 o'clock directions of the spokes, while the other 3 cans were placed at the 1:30, 4:30, 7:30 and 10:30 directions of the spokes.
- the empty 4 inch pots were removed from each assembly and a treated 4 inch soil pot was placed in its place.
- Untreated chickweed plants were evaluated for phytotoxic injury 14 days after treatment. Volatility was assessed by measuring the distance from the center of the treated soil pot to the endpoint at which the bleaching effect was observed on each spoke.
- Sow main crops and weeds after sowing and pre-emergence in the field After testing, spinach, radish, cabbage, sesame, rapeseed, cucumber, watermelon, melon, pumpkin, cassava, soybean, kidney bean, cowpea, kidney bean, lentil, loofah, sorghum, Garlic, rice, corn, cauliflower, cabbage, and coriander were all safe to compound 1 at a dose of 300g a.i./ha, and it was also effective against barnyard grass, stephenia, crabgrass, wormwood, shepherd's purse, pig's weed, chickweed, and ryegrass The main weeds control effect is excellent, such as , brome, and big-sui Kan Mai Niang.
- the required active ingredient B is purchased from a reagent company or synthesized by a known method.
- the original medicines all use acetone as a solvent, and are diluted with an aqueous solution of 0.1% emulsifier Tween-80, and are diluted immediately after use.
- Weeds are cultivated in pots, using 180 ⁇ 140mm plastic nutrient pots, placed in enamel trays, and filled with surface soil (4/5 places) collected from the farmland and air-dried and sieved.
- the initial soil humidity is controlled at 20%, and the seeds are selected.
- For plump and uniform weed seeds soak them in warm water at 25°C for 6 hours, and germinate them in a biochemical incubator (dark) at 28°C. Place the newly white weed seeds evenly on the soil surface, and then cover with soil 0.5- 1cm.
- Cultivation is carried out in a controlled sunlight greenhouse at a temperature of 20-30°C, natural light, and a relative humidity of 57%-72%.
- Each treatment was repeated 4 times, each treatment was 4 pots, and 20 weed seeds were sown in each pot.
- the test shared the medicine 1 time. When the weeds are at the 1.5-2 leaf stage, thin the seedlings, keep 10 weeds in each pot, and keep 10 plants for each treatment, and then continue to cultivate until 2-3 leaves of barnyardgrass, 5-6 leaves of spinach, and 3 - 4 round leaves, 3-5 leaves of Amaranthus retroflexus, barnyardgrass, ryegrass multiflora and 3 leaves of crabgrass for treatment.
- test materials Place the cultured test materials evenly on a platform with an area of 0.5m 2 , spray the stems and leaves with a 3WP-2000 walking spray tower, the spray volume is 450 kg/ha, and the spray pressure is 0.3MPa. After all the liquid medicine is sprayed, close the air valve, and after 30 seconds, open the door of the spray tower and take out the nutrition bowl. Then open the air valve, spray 50mL of water, and clean the spray pipe. After treatment, the test materials were transferred to the greenhouse for routine cultivation.
- the weeds are cultivated in a controlled solar greenhouse with a temperature of 20-30°C, natural light, and a relative humidity of 57%-72%.
- the test soil is quantitatively filled to 3/4 of the pot, and then watered from the bottom of the pot to make the soil completely wet to saturated. Weed seeds of the tested weeds were accelerated to dew white, and then evenly and quantitatively sowed on the surface, covered with soil 0.5-1cm according to the size of the seeds, and set aside 72 hours after sowing.
- Each treatment was repeated 4 times, each treatment had 4 pots, and 20 weed seeds were sown in each pot.
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Abstract
Description
化合物序号 | 马唐 | 千金子 | 苘麻 | 日本看麦娘 | 水稻 | 小麦 |
1 | 5 | 5 | 5 | 4 | 1 | 1 |
对照化合物A | 3 | 2 | 4 | 3 | 2 | 3 |
对照化合物B | 3 | 4 | 3 | 4 | 3 | 4 |
Claims (10)
- 根据权利要求1所述的3-异恶唑烷酮类化合物,其特征在于,Q 1、Q 2分别独立地代表O;R 1、R 2分别独立地代表甲基。
- 一种除草组合物,其特征在于,其包括(i)除草有效量的权利要求1或2所述的3-异恶唑烷酮类化合物中的至少一种。
- 根据权利要求4所述的组合物,其特征在于,还包括(ii)一种或多种除草有效量的另外的除草剂和/或安全剂。
- 根据权利要求5所述的组合物,其特征在于,所述另外的除草剂选自以下化合物中的一种或两种以上:硝磺草酮、呋喃磺草酮、双环磺草酮、双唑草酮、环吡氟草酮、三唑磺草酮、苯唑氟草酮、fenquinotrione、 异噁唑草酮、氟咯草酮、吡氟酰草胺、氟吡酰草胺、氟丁酰草胺、氟啶草酮、异噁草松、bixlozone、苄嘧磺隆、吡嘧磺隆、氯吡嘧磺隆、丙嗪嘧磺隆、嗪吡嘧磺隆、乙氧磺隆、甲基二磺隆、烟嘧磺隆、氟酮磺草胺、五氟磺草胺、甲氧咪草烟、咪唑乙烟酸、双氟磺草胺、双草醚、乙氧氟草醚、氟磺胺草醚、 噁草酮、丙炔噁草酮、甲磺草胺、双唑草腈、丙炔氟草胺、环戊噁草酮、tiafenacil、苯嘧磺草胺、trifludimoxazin、Epyrifenacil、 苯嘧草唑、莠去津、扑草净、西草净、特丁津、特丁净、莠灭净、嗪草酮、氨唑草酮、绿麦隆、异丙隆、敌草隆、敌稗、灭草松、辛酰溴苯腈、仲丁灵、二甲戊灵、氟硫草定、乙草胺、丁草胺、丙草胺、异丙甲草胺、苯噻酰草胺、精异丙甲草胺、氟噻草胺、敌草胺、砜吡草唑、莎稗磷、二甲酚草胺、四唑酰草胺、三唑酰草胺、精二甲吩草胺、溴丁酰草胺、苄草丹、禾草敌、二氯喹啉酸、氯氟吡氧乙酸、氯氟吡氧乙酸异辛酯、氟氯吡啶酯、麦草畏、氯氟吡啶酯、2-甲基-4-氯苯氧乙酸、2-甲基-4-氯-苯酚乙硫酯、2-甲基-4-氯苯氧乙酸钠、2-甲基-4-氯苯氧乙酸异辛酯、2,4-二氯苯氧乙酸丁酯、2,4-二氯苯氧乙酸异辛酯、 2,4-二氯苯氧基乙酸、2甲4氯二甲铵盐、三嗪氟草胺、茚嗪氟草胺、苯草醚、环庚草醚、四氟咯草胺、噁嗪草酮。
- 根据权利要求6所述的组合物,其特征在于,所述除草组合物中有效成分(i)和(ii)中另外的除草剂的重量比为1:1000~1000:1、1:800~800:1、1:600~600:1、1:500~500:1、1:400~400:1、1:300~300:1、1:200~200:1、1:180~180:1、1:150~150:1、1:120~120:1、1:100~100:1、1:80~80:1、1:50~50:1、1:30~30:1、1:20~20:1、1:10~10:1、1:5~1:1或1:1~5:1。
- 根据权利要求4-7任意一项所述的组合物,其特征在于,还包括(iii)农业化学上可接受的制剂助剂。
- 一种防治不希望的植物的方法,其特征在于,包括将除草有效量的权利要求1或2所述的3-异恶唑烷酮类化合物中的至少一种或权利要求4-8任意一项所述的除草组合物施用至植物或者其场所或施用至土壤或水体以防治不希望的植物出苗或生长;优选地,所述不希望的植物包括除草剂抗性或耐受性杂草物种。
- 如权利要求1或2所述的3-异恶唑烷酮类化合物中的至少一种或权利要求4-8任意一项所述的除草组合物在控制不希望的植物上的用途,优选地,将所述的3-异恶唑烷酮类化合物用于防除有用作物中的杂草;更优选地,所述有用作物包括转基因作物或者基因组编辑技术处理过的作物,所述杂草包括除草剂抗性或耐受性杂草物种。
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US4405357A (en) * | 1980-06-02 | 1983-09-20 | Fmc Corporation | Herbicidal 3-isoxazolidinones and hydroxamic acids |
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WO1992010095A1 (en) * | 1990-12-12 | 1992-06-25 | Zeneca Inc. | Antidoting herbicidal 3-isoxazolidinone compounds |
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DATABASE REGISTRY ANONYMOUS : " 3-Isoxazolidinone, 2-[(2-bromo-4-chlorophenyl)methyl]-4,4-dimethyl- (CA INDEX NAME) OTHER CA INDEX NAMES: CN - 2-[(2-Bromo-4-chlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone MF - C12 H13 Br Cl N O2 SR - CAS Client Services LC - STN Files: CA, CAPLUS tektronix-4SGJGSJ", XP093037291, retrieved from STN * |
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