CN107922333B - 新的炔基取代的3-苯基吡咯烷-2,4-二酮及其作为除草剂的用途 - Google Patents
新的炔基取代的3-苯基吡咯烷-2,4-二酮及其作为除草剂的用途 Download PDFInfo
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- CN107922333B CN107922333B CN201680047578.XA CN201680047578A CN107922333B CN 107922333 B CN107922333 B CN 107922333B CN 201680047578 A CN201680047578 A CN 201680047578A CN 107922333 B CN107922333 B CN 107922333B
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- NPTDXPDGUHAFKC-UHFFFAOYSA-N ethynylcyclopropane Chemical group C#CC1CC1 NPTDXPDGUHAFKC-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
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- VAIZTNZGPYBOGF-CYBMUJFWSA-N fluazifop-P-butyl Chemical group C1=CC(O[C@H](C)C(=O)OCCCC)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 VAIZTNZGPYBOGF-CYBMUJFWSA-N 0.000 description 1
- UOUXAYAIONPXDH-UHFFFAOYSA-M flucarbazone-sodium Chemical compound [Na+].O=C1N(C)C(OC)=NN1C(=O)[N-]S(=O)(=O)C1=CC=CC=C1OC(F)(F)F UOUXAYAIONPXDH-UHFFFAOYSA-M 0.000 description 1
- 238000009477 fluid bed granulation Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
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- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- MFSWTRQUCLNFOM-SECBINFHSA-N haloxyfop-P-methyl Chemical group C1=CC(O[C@H](C)C(=O)OC)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl MFSWTRQUCLNFOM-SECBINFHSA-N 0.000 description 1
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- 150000002430 hydrocarbons Chemical class 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-O hydron;quinoline Chemical group [NH+]1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-O 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- MWKVXOJATACCCH-UHFFFAOYSA-N isoxadifen-ethyl Chemical group C1C(C(=O)OCC)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 MWKVXOJATACCCH-UHFFFAOYSA-N 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
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- 229910021645 metal ion Inorganic materials 0.000 description 1
- ARQKNEVOEUNWGO-UHFFFAOYSA-N methyl 2-(4-bromo-2,6-dimethylphenyl)acetate Chemical compound COC(=O)CC1=C(C)C=C(Br)C=C1C ARQKNEVOEUNWGO-UHFFFAOYSA-N 0.000 description 1
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- BACHBFVBHLGWSL-UHFFFAOYSA-N methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-UHFFFAOYSA-N 0.000 description 1
- VWGAYSCWLXQJBQ-UHFFFAOYSA-N methyl 4-iodo-2-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylsulfamoyl]benzoate Chemical group COC(=O)C1=CC=C(I)C=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 VWGAYSCWLXQJBQ-UHFFFAOYSA-N 0.000 description 1
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- 125000002950 monocyclic group Chemical group 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
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- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 210000003463 organelle Anatomy 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- 238000010651 palladium-catalyzed cross coupling reaction Methods 0.000 description 1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
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- MGOHCFMYLBAPRN-UHFFFAOYSA-N pinoxaden Chemical compound CCC1=CC(C)=CC(CC)=C1C(C1=O)=C(OC(=O)C(C)(C)C)N2N1CCOCC2 MGOHCFMYLBAPRN-UHFFFAOYSA-N 0.000 description 1
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- 229920000136 polysorbate Polymers 0.000 description 1
- 230000032361 posttranscriptional gene silencing Effects 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- FROBCXTULYFHEJ-OAHLLOKOSA-N propaquizafop Chemical compound C1=CC(O[C@H](C)C(=O)OCCON=C(C)C)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 FROBCXTULYFHEJ-OAHLLOKOSA-N 0.000 description 1
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- OSUHJPCHFDQAIT-GFCCVEGCSA-N quizalofop-P-ethyl Chemical group C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 OSUHJPCHFDQAIT-GFCCVEGCSA-N 0.000 description 1
- BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 description 1
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- 108091092562 ribozyme Proteins 0.000 description 1
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- 229930000044 secondary metabolite Natural products 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000003513 sheep sorrel Nutrition 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
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- 125000000542 sulfonic acid group Chemical group 0.000 description 1
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- 230000001629 suppression Effects 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
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- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000004753 textile Substances 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
- 238000012546 transfer Methods 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
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
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- 239000002023 wood Substances 0.000 description 1
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- 229910052727 yttrium Inorganic materials 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/46—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid
- C07C57/48—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid having unsaturation outside the aromatic rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01C—PLANTING; SOWING; FERTILISING
- A01C1/00—Apparatus, or methods of use thereof, for testing or treating seed, roots, or the like, prior to sowing or planting
- A01C1/08—Immunising seed
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01G—HORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
- A01G7/00—Botany in general
- A01G7/06—Treatment of growing trees or plants, e.g. for preventing decay of wood, for tingeing flowers or wood, for prolonging the life of plants
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
- A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C57/42—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings having unsaturation outside the rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/54—Spiro-condensed
-
- 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
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Landscapes
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Dentistry (AREA)
- Toxicology (AREA)
- Forests & Forestry (AREA)
- Ecology (AREA)
- Biodiversity & Conservation Biology (AREA)
- Botany (AREA)
- Soil Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
本发明涉及通式(I)的新的有效的炔基取代的3‑苯基吡咯烷‑2,4‑二酮或其农业化学上可接受的盐,其中X=C1‑C4‑烷基、C1‑C4‑卤代烷基或C3‑C6‑环烷基;Y=C1‑C4‑烷基或C3‑C6‑环烷基;n=1、2或3;m=1或2;R1=C1‑C6‑烷基或C3‑C6‑环烷基;R2=氢或甲基;R3=C1‑C3‑烷氧基‑C1‑C3‑烷基,或具有氧或硫原子的饱和的五元或六元杂环;G=氢、可裂解基团L或阳离子E。本发明还涉及在培养有用植物中本发明的化合物防治杂草和不想要的草的用途。
Description
本发明涉及通式(I)的新的有效的炔基取代的3-苯基吡咯烷-2,4-二酮或其农业化学上可接受的盐,及其用于防治有用的植物作物中杂草和禾本科杂草(weed grass)的用途。
3-芳基吡咯烷-2,4-二酮的化合物类别及其制备和作为除草剂的用途在现有技术中是众所周知的。
然而,此外,还记载了例如具有除草、杀昆虫或杀真菌作用的双环3-芳基吡咯烷-2,4-二酮衍生物(EP-A-355 599、EP-A-415 211和JP-A 12-053670等)和取代的单环3-芳基吡咯烷-2,4-二酮衍生物(EP-A-377 893和EP-A-442 077等)。
由WO 96/82395、WO 98/05638、WO 01/74770、WO 14/032702或WO15/040114还已知具有除草作用的炔基取代的N-苯基吡咯烷-2,4-二酮。
这些除草剂对有害植物的效力取决于许多参数,例如所使用的施用率、制剂形式(制剂)、每种情况下待防治的有害植物、有害植物的谱、气候和土壤比例以及除草剂的作用时间和/或降解速率。为了开发足够的除草效果,许多来自3-芳基吡咯烷-2,4-二酮类的除草剂要求高的施用率和/或窄的有害植物谱,这使得它们的应用在经济上不具吸引力。因此,需要具有改进的性能并且在经济上有吸引力且同时有效的可替代的除草剂。
因此,本发明的目的是提供不具有所述缺点的新化合物。
因此,本发明涉及新的通式(I)的炔基取代的N-苯基吡咯烷-2,4-二酮或其农业化学上可接受的盐,
其中
X=C1-C4-烷基、C1-C4-卤代烷基或C3-C6-环烷基,
Y=C1-C4-烷基或C3-C6-环烷基,
n=1、2或3,
m=1或2,
R1=C1-C6-烷基或C3-C6-环烷基,
R2=氢或甲基,
R3=C1-C3-烷氧基-C1-C3-烷基,或具有氧或硫原子的饱和的五元或六元杂环,
G=氢、可裂解基团L或阳离子E;其中
L=以下基团之一
其中
R4=C1-C4-烷基或C1-C3-烷氧基-C1-C4-烷基,
R5=C1-C4-烷基,
R6=C1-C4-烷基,未取代的苯基或用卤素、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、硝基或氰基取代一次或多次的苯基,
R7、R7‘=各自彼此独立地为甲氧基或乙氧基,
R8和R9=各自彼此独立地为甲基、乙基、苯基或一起形成饱和的5-、6-或7-元环,或一起形成具有氧或硫原子的饱和的5-、6-或7-元杂环,
E=碱金属离子、碱土金属的离子等价物、铝的离子等价物或过渡金属的离子等价物、卤化镁阳离子,或铵离子,其中任选一个、两个、三个或全部四个氢原子被相同或不同的选自氢、C1-C5-烷基、C1-C5-烷氧基或C3-C7-环烷基的基团取代,所述基团可各自被氟、氯、溴、氰基、羟基取代一次或多次或被一个或多个氧或硫原子间隔,或环状仲或叔脂族或杂脂族铵离子,例如吗啉鎓、硫代吗啉鎓、哌啶鎓、吡咯烷鎓或在每种情况下质子化的1,4-二氮杂双环[2.2.2]辛烷(DABCO)或1,5-二氮杂双环[4.3.0]十一碳-7-烯(DBU),或杂环铵阳离子,例如在每种情况下质子化的吡啶、2-甲基吡啶、3-甲基吡啶、4-甲基吡啶、2,4-二甲基吡啶、2,5-二甲基吡啶、2,6-二甲基吡啶、5-乙基-2-甲基吡啶、吡咯、咪唑、喹啉、喹喔啉、1,2-二甲基咪唑、1,3-二甲基咪唑鎓甲基硫酸盐,或进一步为锍离子。
式(I)提供了本发明化合物的一般定义。在上文和下文提到的式中给出的基团的优选取代基或范围在下文中说明:
在式(I)和所有式中,具有两个以上碳原子的烷基可以是直链或支链的。烷基为例如甲基、乙基、正异丙基或异丙基、正丁基、异丁基、叔丁基或2-丁基、戊基(例如正戊基、2,2-二甲基丙基和3-甲基丁基)。环烷基为具有3至6个碳原子的碳环饱和环体系,例如环丙基、环丁基、环戊基或环己基。
卤素为氟、氯、溴或碘。
根据取代基的类型,式(I)的化合物可以几何和/或光学异构体或异构体混合物的形式存在,其不同的组成可任意地以常规方式分离。纯的异构体以及互变异构体、异构体或对映异构体混合物、它们的制备和用途,以及包含它们的组合物均由本发明提供。然而,为了简单起见,下文使用的术语为式(I)的化合物,尽管纯化合物以及任选地具有不同比例的异构体和互变异构化合物的混合物也是预期的。
优选这样的化合物,其中
X=C1-C4-烷基或C3-C6-环烷基,
Y=C1-C4-烷基或C3-C6-环烷基,
n=1、2或3,
m=1或2,
R1=甲基、乙基、异丙基或环丙基,
R2=氢或甲基,
R3=C1-C3-烷氧基-C1-C3-烷基,
G=氢、可裂解基团L或阳离子E,其中
L=以下基团之一
其中
R4=C1-C4-烷基,
R5=C1-C4-烷基,
R6=C1-C4-烷基,未取代的苯基或用卤素、C1-C4-烷基或C1-C4-烷氧基取代的苯基,
R7、R7‘=彼此独立地为甲氧基或乙氧基,
E=碱金属离子、碱土金属的离子等价物、铝的离子等价物或过渡金属的离子等价物,或铵离子,其中任选一个、两个、三个或全部四个氢原子被相同或不同的选自氢或C1-C5-烷基的基团取代;或叔脂族或杂脂族铵离子;或杂环铵阳离子,例如在每种情况下质子化的吡啶、喹啉、喹喔啉、1,2-二甲基咪唑、1,3-二甲基咪唑鎓甲基硫酸盐;或者也为锍离子。
特别优选这样的通式(I)的化合物,其中
X=甲基、乙基或环丙基,
Y=甲基或乙基,
n=1或2,
m=1或2,
R1=甲基、乙基、异丙基或环丙基,
R2=氢,
R3=CH3CH2OCH2-或CH3OCH2-,
G=氢、可裂解基团L或阳离子E,其中
L=以下基团之一
其中
R4=C1-C4-烷基,
R5=C1-C4-烷基,
E=金属离子、碱土金属的离子等价物、铝的离子等价物、过渡金属的离子等价物或为卤化镁阳离子、四-C1-C5烷基铵阳离子或杂环铵阳离子,例如在每种情况下质子化的吡啶或喹啉,或者也为锍离子。
非常特别优选这样的式(I)的化合物,其中
X=甲基或乙基,
Y=甲基或乙基
n=1或2,
m=1或2,
R1=甲基、乙基、异丙基或环丙基,
R2=氢,
R3=CH3CH2OCH2-或CH3OCH2-,
G=氢、可裂解基团L或阳离子E,其中
L=以下基团之一
其中
R4=甲基、乙基或异丙基,
R5=甲基或乙基,
E=钠、钾、三甲基铵、吡啶鎓、喹啉鎓或三甲基锍阳离子或钙或镁的离子等价物。
本发明的通式(I)的化合物的制备原则上是已知的和/或可以根据文献中已知的方法进行,例如通过
a)任选地在合适的溶剂或稀释剂的存在下,用合适的碱使通式(II)的化合物环化,形式上断开基团R10OH,
其中,X、Y、R1、R2和R3,以及n和m具有上文给出的含义,并且R10为烷基,优选甲基或乙基,或
b)任选地在合适的溶剂或稀释剂以及合适的碱的存在下,使通式Ia的化合物与通式(III)的化合物反应
其中,X、Y、R1、R2和R3,以及n和m具有上文给出的含义,
Hal-L (III)
其中,L具有上文给出的含义,Hal为卤素,优选氯或溴,或可为磺酸基团。
c)任选地在合适的催化剂和合适的碱的存在下,使通式(IV)的化合物与通式(V)的合适的炔基试剂反应,
其中X、Y、R2和R3、m、n和G具有上文给出的含义,且U为合适的离去基团,
其中R3具有上文给出的含义,W为氢或合适的离去基团。合适的离去基团W为例如卤素原子如氯、溴或碘;烷基磺酸酯基团如三氟甲磺酸酯、甲磺酸酯或壬磺酸酯;氯化镁、氯化锌、三烷基锡基团和硼酸基团如B(OH)2或-B(O烷基)2。特别地,Pd0络合物非常适合作为催化剂,其中在许多情况下Cu(I)盐的加入可能是非常有利的。
所记载的方法在现有技术的文献中是已知的,此外在关键词“钯催化的交叉偶联”、“Sonogashira-、Negishi-、Suzuki-、Stille-或Kumada偶联”下也是如此。
或者,通式(IV)的化合物还可以与通式(VI)的炔基试剂在上述偶合方法的类似应用中反应,然后裂解成通式(VIII)的乙炔基化合物,并用合适的烷基化试剂使它们最终转化为本发明的化合物(I),其中在每种情况下,X、Y、R2、R3、n、m、G和W具有所述的含义,并且可裂解基团R11可以为例如基团(C1-C4-烷基)2C-OH。
同样在文献中已知的这项技术例如在Beilstein Journal of OrganicChemistry2011,7(55),426-431和Catalysis Communications 2015,60,82-87中被更详细地解释。
另一种选择是在上述偶合方法的类似应用中使通式(IV)的化合物与通式(IX)的炔基试剂反应。然后,可以在合适的条件下裂解基团R12,得到其中R3=Me的本发明的式(I)的化合物,其中在每种情况下X、Y、R2、n、m、G和W具有所述含义。R12为C1-C4-三烷基甲硅烷基。
在文献中已知的这项技术例如记载在Journal of Medicinal Chemistry 2007,50(7),1627-1634中。
可经由已知方法通过将通式(VI)的氨基酸酯与通式(VII)的苯基乙酸反应来制备所需的通式(II)的前体,其中X、Y、R1、R2和R3和R10以及n和m具有上述含义,任选地通过加入吸水剂并任选在合适的溶剂或稀释剂存在下进行。
用于制备具有通式(II)的化合物的另一个变型例如还包括使具有通式(IIa)的化合物——其中X、Y、R2、R3、R10、R11、n和m和U具有上文给出的含义——通过已经描述的交叉耦合方法进行反应。
通式(VII)的苯基乙酸——即2,6-二甲基-4-炔丙基苯基乙酸——原则上在WO2015/040114中提及,但是其没有记载获得这些化合物的路径。
然而,它们可以根据文献中已知的方法制备,例如通过使通式(X)的化合物——其中X、Y、U、W、R3、R10和R11如上文所定义且R=C1-C4-烷基——再次经由上文已经描述的方法与通式(V)或(V)的试剂反应。
本发明的式(I)的化合物(和/或其盐)在下文中统称为“本发明的化合物”,对广谱的经济上重要的单和双子叶一年生杂草具有优异的除草活性。活性成分还能有效地作用于从根茎、根状茎和其他多年生器官发芽且难以防治的多年生杂草。
因此,本发明还提供一种防治不需要的植物或调节植物(优选在植物作物中)的生长的方法,其中将本发明的一种或多种化合物施用于植物(例如有害植物,例如单子叶或双子叶杂草或不需要的作物植物)、种子(例如谷物、种子或无性繁殖体,如块茎或带有萌芽的枝条部位)或施用于植物在其上生长的区域(例如培育下的区域)。本发明的化合物可以例如在播种前施用(如果合适也可混入土壤)、出苗前或出苗后施用。具体地,可以提及例如许多可通过本发明的化合物防治的单子叶和双子叶杂草植物群,而不因命名而限定于某些种类。
以下属的单子叶有害植物:山羊草属(Aegilops)、冰草属(Agropyron)、剪股颖属(Agrostis)、看麦娘属(Alopecurus)、Apera属、燕麦属(Avena)、臂形草属(Brachiaria)、雀麦属(Bromus)、蒺藜草属(Cenchrus)、鸭跖草属(Commelina)、狗牙根属(Cynodon)、莎草属(Cyperus)、龙爪茅属(Dactyloctenium)、马唐属(Digitaria)、稗属(Echinochloa)、荸荠属(Eleocharis)、蟋蟀草属(Eleusine)、画眉草属(Eragrostis)、野黍属(Eriochloa)、羊茅属(Festuca)、飘拂草属(Fimbristylis)、异蕊花属(Heteranthera)、白茅属(Imperata)、鸭嘴草属(Ischaemum)、千金子属(Leptochloa)、黑麦草属(Lolium)、雨久花属(Monochoria)、黍属(Panicum)、雀稗属(Paspalum)、虉草属(Phalaris)、梯牧草属(Phleum)、早熟禾属(Poa)、筒轴茅属(Rottboellia)、慈姑属(Sagittaria)、莞草属(Scirpus)、狗尾草属(Setaria)、高粱属(Sorghum)。
以下属的双子叶杂草:苘麻属(Abutilon)、苋属(Amaranthus)、豚草属(Ambrosia)、Anoda属、春黄菊属(Anthemis)、Aphanes属、艾属(Artemisia)、滨藜属(Atriplex)、雏菊属(Bellis)、鬼针属(Bidens)、荠属(Capsella)、飞廉属(Carduus)、决明属(Cassia)、矢车菊属(Centaurea)、藜属(Chenopodium)、蓟属(Cirsium)、旋花属(Convolvulus)、曼陀罗属(Datura)、山蚂蝗属(Desmodium)、刺酸模属(Emex)、糖芥属(Erysimum)、大戟属(Euphorbia)、鼬瓣花属(Galeopsis)、牛膝菊属(Galinsoga)、拉拉藤属(Galium)、芙蓉属(Hibiscus)、番薯属(Ipomoea)、地肤属(Kochia)、野芝麻属(Lamium)、独行菜属(Lepidium)、母草属(Lindernia)、母菊属(Matricaria)、薄荷属(Mentha)、山靛属(Mercurialis)、Mullugo属、勿忘我属(Myosotis)、罂粟属(Papaver)、牵牛属(Pharbitis)、车前属(Plantago)、蓼属(Polygonum)、马齿苋属(Portulaca)、毛茛属(Ranunculus)、萝卜属(Raphanus)、蔊菜属(Rorippa)、节节菜属(Rotala)、酸模属(Rumex)、猪毛菜属(Salsola)、千里光属(Senecio)、田菁属(Sesbania)、黄花稔属(Sida)、白芥属(Sinapis)、茄属(Solanum)、苦苣菜属(Sonchus)、尖瓣花属(Sphenoclea)、繁缕属(Stellaria)、蒲公英属(Taraxacum)、菥蓂属(Thlaspi)、车轴草属(Trifolium)、荨麻属(Urtica)、婆婆纳属(Veronica)、堇菜属(Viola)、苍耳属(Xanthium)。
如果在发芽前将本发明的化合物施用至土壤表面,则完全阻止杂草幼苗出土或者使杂草生长直至其达到子叶期,但之后它们就停止生长,并最终在三至四周后完全死亡。
如果在出苗后将活性化合物施用至植物的绿色部位,则在处理后生长停止,并且有害植物停留在施用时间点的生长阶段,或者其在一段时间后完全死亡,从而以这种方式在非常早的时期并以持续的方式消除对作物植物有害的杂草的竞争。
虽然本发明的化合物对单子叶和双子叶杂草具有优异的除草活性,但对经济上重要的作物的作物植物仅具有微小程度的损害或者完全没有损害,这取决于本发明的具体化合物的结构及其施用率,所述经济上重要的作物例如:以下属的双子叶作物:花生属(Arachis)、甜菜属(Beta)、芸苔属(Brassica)、黄瓜属(Cucumis)、南瓜属(Cucurbita)、向日葵属(Helianthus)、胡萝卜属(Daucus)、大豆属(Glycine)、棉属(Gossypium)、番薯属(Ipomoea)、莴苣属(Lactuca)、亚麻属(Linum)、番茄属(Lycopersicon)、烟草属(Nicotiana)、菜豆属(Phaseolus)、豌豆属(Pisum)、茄属(Solanum)、蚕豆属(Vicia);或以下属的单子叶作物:葱属(Allium)、凤梨属(Ananas)、天门冬属(Asparagus)、燕麦属(Avena)、大麦属(Hordeum)、稻属(Oryza)、黍属(Panicum)、甘蔗属(Saccharum)、黑麦属(Secale)、高粱属(Sorghum)、小黑麦属(Triticale)、小麦属(Triticum)、玉蜀黍属(Zea),特别是玉蜀黍属和小麦属。出于这些原因,本发明的化合物高度适用于在作物植物中例如农业有用植物或观赏植物中选择性地防治不想要的植物的生长。
此外,本发明的化合物(取决于它们具体的结构和所用的施用率)在作物植物中具有出色的生长调节特性。它们以调节作用参与植物自身的代谢,并且因此可以用于可控地影响植物组成并使采收便利,例如通过引发脱水和使植株矮小生长。而且,它们也适用于一般的防治和抑制不想要的营养生长而在这个过程中不破坏植物。抑制营养生长在许多单子叶和双子叶作物中起重要作用,这是因为例如可由此减少或完全防止倒伏。
活性成分凭借其除草和植物生长调节特性也可以用于在遗传修饰植物或通过常规诱变修饰的植物的作物中防治有害植物。通常,转基因植物的特征在于其具有特别有利的特性,例如对某些农药(特别是某些除草剂)具有抗性,对植物病害或植物病害病原体具有抗性,所述病原体例如某些昆虫或微生物,例如真菌、细菌或病毒。其他特殊性质例如涉及采收物的产量、质量、储存性、组成和具体成分。例如,已知淀粉含量提高或淀粉品质改变的转基因植物,或其中采收物具有不同脂肪酸组成的那些。
关于转基因作物,优选在有用植物和观赏性植物中经济上重要的转基因作物上使用本发明的化合物,例如在谷物,如小麦、大麦、黑麦、燕麦、黍、稻和玉米,或其他作物如甜菜、棉花、大豆、油菜、马铃薯、番茄、豌豆和其他蔬菜中。优选地,本发明的化合物可在对除草剂的植物毒性作用具有抗性或已通过重组方式产生抗性的有用植物作物中用作除草剂。
制备与现有植物相比具有改进特性的新植物的常规方法包括例如常规育种方法和产生突变体。或者,具有改进特性的新植物可借助重组方法生成(参见,例如,EP-A-0221044、EP-A-0131624)。例如,已描述以下几种情况:
-用于修饰植物中合成的淀粉(例如WO 92/11376、WO 92/14827、WO 91/19806)的遗传修饰作物植物,
-对某些草铵磷(glufosinate)类除草剂(参见例如EP-A-0242236、EP-A-0242246)或草甘膦(gluphosate)类除草剂(WO 92/00377)或磺酰脲类除草剂(EP-A-0257993、US-A-5013659)具有抗性的转基因作物植物,
-能产生苏云金杆菌毒素(Bt毒素)从而使植物对某些害虫具有抗性的转基因作物植物,例如棉花(EP-A-0142924、EP-A-0193259),
-具有改变的脂肪酸组成的转基因作物植物(WO 91/13972),
-具有新成分或次级代谢物的遗传修饰作物植物,所述新成分或次级代谢产物为例如产生增强的抗病性的新的植物抗毒素(phytoalexin)(EPA 309862、EPA0464461),
-具有减少的光呼吸作用的遗传修饰植物,其具有较高的产量和较高的胁迫耐受性(EPA 0305398),
-产生药学或诊断方面的重要蛋白的转基因作物植物(“分子制药”),
-以更高产量或更好品质为特征的转基因作物植物,
-以例如上述新特性的组合(“基因叠加”)为特征的转基因作物植物。
许多可用于制备具有改进特性的新转基因植物的分子生物技术原则上是已知的,参见例如I.Potrykus和G.Spangenberg(编)Gene Transfer to Plants,Springer LabManual(1995),Springer Verlag Berlin,Heidelberg.或者Christou,"Trends in PlantScience"1(1996)423-431。
为了进行这类重组操作,可以将能够通过重组DNA序列产生突变或序列改变的核酸分子引入质粒。借助标准方法,可以例如进行碱基取代、移除部分序列或加入天然或合成的序列。为了将DNA片段彼此连接,可以将衔接物(adapter)或连接物(linker)置于片段上;例如参见,Sambrook et al.,1989,Molecular Cloning,A Laboratory Manual,第二版Cold Spring Harbor Laboratory Press,Cold Spring Harbor,NY;或Winnacker"Geneund Klone",VCH Weinheim第二版1996。
例如,产生具有降低活性的基因产物的植物细胞可以通过下述方法实现:通过表达至少一种相应的反义RNA、正义RNA用于实现共抑制效应,或者通过表达至少一种能够特定地分裂上述基因产物的转录物的具有合适结构的核酶。为此,可以首先使用包括基因产物的全部编码序列——包括任何可能存在的侧翼序列——的DNA分子,以及仅包含部分编码序列的DNA分子,在这种情况下,这些部分编码序列必须足够长,以便在细胞中产生反义作用。也可以使用与所述基因产物的编码序列具有高度同源性但并不完全相同的DNA序列。
当在植物中表达核酸分子时,所合成的蛋白可被定位在植物细胞的任何所需的区室中。然而,为了实现在特定区室中的定位,可以例如将编码区与确保在特定区室中定位的DNA序列相连接。这种序列是本领域技术人员已知的(参见,例如,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)。核酸分子也可以在植物细胞的细胞器中表达。
可以通过已知技术再生转基因植物细胞以产生完整的植物。原则上,所述转基因植物可为任何所需的植物品种的植物,即既可为单子叶植物,也可为双子叶植物。
因此,可以通过对同源(=天然)基因或基因序列的过表达、阻遏或抑制,或者通过异源(=外源)基因或基因序列的表达而获得性质改变的转基因植物。
优选将本发明的化合物用于转基因作物中,所述转基因作物对生长调节剂例如麦草畏(dicamba)具有抗性,或者对抑制重要的植物酶的除草剂,例如乙酰乳酸合成酶(ALS)、EPSP合成酶、谷氨酰胺合成酶(GS)或羟基苯丙酮酸双加氧酶(HPPD)具有抗性,或者对选自磺酰脲、草甘膦、草铵磷或苯甲酰基异噁唑以及类似的活性化合物的除草剂具有抗性。
当将本发明的活性成分用于转基因作物中时,不仅在其他作物中观察到对于有害植物的效果,还经常观察到施用于特定的转基因作物的特殊的效果,例如改变或特别是增宽的可以防治的杂草谱、改变的施用时可以使用的施用率、优选地与对转基因作物具有抗性的除草剂的良好的相容性,以及对转基因作物植物的生长和产量的影响。
因此,本发明还涉提供本发明的化合物作为除草剂用于防治转基因作物植物中的有害植物的用途。
在本发明的一个优选实施方案中,通式(I)的化合物也可用于防治那些有害植物,例如剪股颖属、看麦娘属、阿披拉草属(Apera)、燕麦属、臂形草属、雀麦属、蒺藜草属、马唐属、稗属、蟋蟀草属、野黍属、千金子属、黑麦草属,露籽草属(Ottochloa)、黍属、狼尾草属、虉草属、早熟禾属、筒轴茅属、狗尾草属和/或高粱杂草,
-这些有害植物对一种或多种抑制乙酰辅酶A羧化酶(ACCase)的除草剂具有抗性。该抑制ACCase的除草剂特别为唑啉草酯(pinoxaden)、炔草酯(clodinafop-propargyl)、精恶唑禾草灵(fenoxaprop-P-ethyl)、禾草灵(diclofop-methyl)、氟禾草灵(fluazifop-P-butyl)、高效氟吡甲禾灵(haloxyfop-P-methyl)、精喹禾灵(quizalofop-P-ethyl)、喔草酯(propaquizafop)、氰氟草酯(cyhalofop-butyl)、烯草酮(clethodim)、稀禾定(sethoxydim)、噻草酮(cycloxydim)、肟草酮(tralkoxydim)或丁氧环酮(butroxydim);
-和/或对草甘膦具有抗性,
-和/或对一种或多种抑制乙酰乳酸合酶(ALS)的除草剂具有抗性,例如一种或多种磺酰脲类除草剂(例如甲基碘磺隆(iodosulphurone-methyl)、甲基二磺隆(mesosulphurone-methyl)、苯磺隆(tribenuron-methyl)、醚苯磺隆(triasulphurone)、氟磺隆(prosulphurone)、磺酰磺隆(sulphosulphurone)、吡嘧磺隆(pyrazosulphurone-ethy)、稻禾隆(bensulphurone-methyl)、烟嘧磺隆(nicosulphurone)、啶嘧磺隆(flazasulphurone)、iofensulphurone、甲磺隆(metsulphurone-methyl)或在C.D.S.Tomlin,英国作物保护委员会的(British Crop Protection Council)“ThePesticide Manual”,第15版(2009)或第16版(2012)中公开的任何其他的磺酰脲,和/或一种或多种三唑并嘧啶除草剂(例如双氟磺草胺(florasulam)、啶磺草胺(pyroxsulam)或五氟磺草胺(penoxsulam))和/或一种或多种嘧啶基(硫代或氧基)苯甲酸酯除草剂(例如双草醚钠(bispyribac-sodium)或环酯草醚(pyriftalid))和/或一种或多种磺酰氨基羰基三唑啉酮除草剂(例如噻酮磺隆(thiencarbazone-methyl)、丙苯磺隆钠(propoxycarbazone-sodium)或氟酮磺隆钠钠(flucarbazone-sodium))和/或咪唑啉酮类除草剂(例如甲氧咪草烟(imazamox))。
对ACCase和/或ALS抑制剂和/或草甘膦具有抗性的所述有害杂草的具体实例尤其是大穗看麦娘(Alopecurusmyosuroides)、阿披拉草、(Aperaspica-venti)、野燕麦(Avenafatua)、不实野燕麦(Avenasterilis)、俯仰臂形草(Brachiariadecumbens)、车前状臂形草(Brachiariaplantaginea)、Digitatiahorizontalis、马唐属草(Digitariainsularis)、马唐(Digitariasanguinalis)、光头稗(Echinochloacolona)、稗草(Echinochloa crus-galli)、牛筋草(Eleusineindica)、多花黑麦草(Loliummultiflorum)、硬直黑麦草(Loliumrigidum)、多年生黑麦草(Loliumperenne)、小子虉草(Phalaris minor)、奇异虉草(Phalarisparadoxa)、狗尾草(Setariaviridis)、大狗尾草(Setariafaberi)或金狗尾草(Setariaglauca)。
在本发明一个特别优选的实施方案中,本发明的通式(I)的化合物可以用于抵抗这样的有害植物
-对一种或多种抑制ACCase的除草剂(例如选自上述列表)具有抗性或实际上至少部分基于有害植物的ACCase靶位点发生的一个或多个氨基酸的突变(例如取代)(参见例如SB Powles和Qin Yu,“Evolution in Action:Plants Resistant to Herbicides”,Annu.Rev.Plant Biol,2010,61,第317-347页);和/或
-对草甘膦具有抗性,并且实际上至少部分基于在草甘膦指向的所述杂草中的EPSPS靶位点发生的一个或多个氨基酸的突变(例如取代);和/或
-对一种或多种抑制ALS的除草剂(例如,选自上述ALS抑制性除草剂的列表)并且实际上至少部分基于所述杂草中ALS靶位点发生的一个或多个氨基酸的突变(例如取代)(参见例如S.B.Powles和Qin Yu,“Evolution in Action:Plants Resistant toHerbicides”,Annu.Rev.Plant Biol,2010,61,第317-347页);和/或
-对一种或多种抑制ACCase的除草剂(例如选自上述列表)和/或对草甘膦和/或一种或多种抑制ALS的除草剂(例如选自上述列表)具有抗性,并且实际上至少部分通过代谢诱导具有除草剂耐受性,例如,至少部分归因于细胞色素P450介导的代谢(参见,例如S.B.Powles和Qin Yu,“Evolution in Action:Plants Resistant to Herbicides”,Annu.Rev.Plant Biol,2010,61,第317-347页)。
与来自现有技术的化合物(例如WO2015/040114,化合物42.03)(还参见表9和10中的比较数据)相比,本发明的化合物表现出优异的特性。
本发明的化合物可以以常规剂型中的可湿性粉剂、乳化浓缩剂、可喷洒溶液剂、粉末剂或颗粒剂的形式施用。因此,本发明还提供含有本发明的化合物的除草和植物生长调节组合物。
根据预先给定的的生物和/或物理化学参数,可通过多种方式来配制本发明的化合物。合适的制剂包括,例如:可湿性粉剂(WP)、水溶性粉剂(SP)、水溶性浓缩剂、乳油(EC)、乳剂(EW)(例如水包油乳剂和油包水乳剂)、可喷洒溶液剂、悬浮浓缩剂(SC)、油基分散剂或水基分散剂、油混溶性溶液剂、胶囊悬浮剂(CS)、粉末剂(DP)、拌种产品、用于撒播和土壤施用的颗粒剂、微颗粒形式的颗粒剂(GR)、喷洒颗粒剂、吸收颗粒剂和吸附颗粒剂、水分散性颗粒剂(WG)、水溶性颗粒剂(SG)、ULV制剂、微胶囊剂和蜡剂。这些制剂类型原则上都是已知的,并记载在下列文献中,例如:Winnacker-Küchler,“Chemische Technologie”[ChemicalTechnology],第7卷,C.Hauser Verlag Munich,第4版,1986;Wade van Valkenburg,“Pesticide Formulations”,Marcel Dekker,N.Y.,1973;K.Martens,“Spray Drying”Handbook,第3版.1979,G.Goodwin Ltd.London。
必需的制剂助剂,例如惰性物质、表面活性剂、溶剂和其他添加剂同样也是已知的,并记载在下列文献中,例如:Watkins,"Handbook of Insecticide Dust Diluents andCarriers",第二版,Darland Books,Caldwell N.J.;H.v.Olphen,"Introduction to ClayColloid Chemistry";第二版,J.Wiley&Sons,N.Y.;C.Marsden,"Solvents Guide";第二版,Interscience,N.Y.1963;McCutcheon's"Detergents and Emulsifiers Annual",MCPubl.Corp.,Ridgewood N.J.;Sisley and Wood,"Encyclopedia of Surface ActiveAgents",Chem.Publ.Co.Inc.,N.Y.1964; [Interface-active ethyleneoxide adducts],Wiss.Verlagsgesell.,Stuttgart 1976;Winnacker-Küchler,"Chemische Technologie",第7卷,C.Hanser Verlag Munich,第四版,1986。
基于这些制剂,还可以制备与其他农药活性物质——例如杀昆虫剂、杀螨剂、除草剂和杀真菌剂——以及与安全剂、肥料和/或生长调节剂的结合物,例如以成品制剂或桶混物形式。合适的安全剂是例如吡唑解草酯(mefenpyr-diethyl)、环丙磺酰胺(cyprosulfamide)、双苯噁唑酸(isoxadifen-ethyl)和二氯丙烯胺(dichlormid)。
可湿性粉剂为可均匀分散于水中的制剂,除了含有活性成分和稀释剂或惰性物质之外,其还含有离子型表面活性剂和/或非离子型表面活性剂(湿润剂、分散剂),例如聚氧乙基化烷基酚、聚氧乙基化脂肪醇、聚氧乙基化脂肪胺、脂肪醇聚乙二醇醚硫酸盐、烷基磺酸盐、烷基苯磺酸盐、木素磺酸钠、2,2’-二萘基甲烷-6,6’-二磺酸钠、二丁基萘磺酸钠或油酰基甲基牛磺酸钠。为了制备可湿性粉剂,例如在常规设备例如锤磨机、鼓风研磨机和喷气研磨机中精细研磨具有除草活性的成分,并同时或随后与制剂助剂相混合。
乳油通过下述过程制备:将活性成分溶于有机溶剂(例如丁醇、环己酮、二甲基甲酰胺、二甲苯或相对高沸点的芳香族化合物或烃类)或有机溶剂的混合物中,并加入一种或多种离子型和/或非离子型表面活性剂(乳化剂)。所使用的乳化剂的实例为:烷基芳基磺酸钙盐,例如十二烷基苯磺酸钙;或非离子型乳化剂,例如脂肪酸聚乙二醇酯、烷基芳基聚乙二醇醚、脂肪醇聚乙二醇醚、环氧丙烷-环氧乙烷缩合产物、烷基聚醚、脱水山梨糖醇酯,例如脱水山梨糖醇脂肪酸酯或聚氧乙烯脱水山梨糖醇酯例如聚氧乙烯脱水山梨糖醇脂肪酸酯。
粉末剂通过将活性成分与细分散的固体物质一起研磨而获得,所述固体物质例如滑石、天然粘土(如高岭土、膨润土和叶蜡石)或硅藻土。
悬浮浓缩剂可为水基或油基的。它们可以通过例如使用标准市售的球磨机湿法研磨,并任选地加入例如上文在其他剂型中已经列出的表面活性剂。
乳剂,例如水包油乳剂(EW),可以例如使用水性有机溶剂以及任选的例如在上文其他剂型中已经列出的表面活性剂借助搅拌器、胶磨机和/或静态混合器制备。
颗粒剂可以通过将所述活性成分喷洒在吸附的颗粒状惰性物质上或通过使用粘合剂将活性成分浓缩物施用到载体物质表面而制备,所述载体例如砂、高岭土或颗粒状惰性材料,所述粘合剂例如聚乙烯醇、聚丙烯酸钠或矿物油。合适的活性成分也可以以制备肥料颗粒的常规方式制备成颗粒——如果需要,可以制备为与肥料的混合物。
水分散性颗粒剂通常可以通过常规方法制备,所述常规方法例如喷雾干燥法、流化床制粒法、盘式制粒法、使用高速混合器的混合法以及不使用固体惰性物质的挤出法。
关于盘式、流化床、挤出法和喷雾法颗粒的制备,参见例如:"Spray-DryingHandbook"第三版,1979,G.Goodwin Ltd.,London;J.E.Browning,"Agglomeration",Chemical and Engineering 1967,第147页及后文;"Perry's Chemical Engineer'sHandbook",第5版,McGraw-Hill,New York 1973,第857页中的方法。
关于作物保护组合物制剂的更多细节,参见例如G.C.Klingman,“Weed Controlas a Science”,John Wiley and Sons.,Inc.,New York,1961,第81-96页;和J.D.Freyer,S.A.Evans,“Weed Control Handbook”,第5版,Blackwell Scientific Publications,Oxford,1968,第101-103页。
农业化学制剂通常含有0.1至99重量%、特别是0.1至95重量%的本发明的化合物。
在可湿性粉剂中,活性成分的浓度例如为约10至90重量%,至100重量%的剩余部分由常规制剂成分组成。在乳油中,活性成分的浓度可为约1至90重量%,优选5至80重量%。
粉末形式的制剂含有1至30重量%的活性成分,优选至多5至20重量%的活性成分;可喷洒性溶液剂含有约0.05至80重量%、优选2至50重量%的活性化合物。对于水分散性颗粒剂而言,活性成分含量部分地取决于所述活性化合物以液体形式还是固体形式存在,以及所使用的粒化助剂和填料等。在水分散性颗粒剂中,活性成分的含量为例如1至95重量%,优选10至80重量%。
此外,所提及的活性成分制剂任选地含有在每种情况下常规的粘合剂、润湿剂、分散剂、乳化剂、渗透剂、防腐剂、抗冻剂和溶剂、填料、载体和染料、消泡剂、蒸发抑制剂和影响pH值及粘度的试剂。
基于上述制剂,还可以制备与其他农药活性物质——例如杀昆虫剂、杀螨剂、除草剂和杀真菌剂——以及与安全剂、肥料和/或生长调节剂的结合物,例如以成品制剂或桶混物的形式。
为了应用,市售形式的制剂,如果合适,以常规的方式稀释,例如在可湿性粉剂、乳油、分散剂和水分散性颗粒剂的情况下,用水稀释。粉末形式的制剂、适于土壤施用的颗粒剂或适于撒播的颗粒剂和可喷洒溶液剂通常在施用前不用其他惰性物质稀释。
式(I)的化合物所需的施用率根据外界条件变化,所述条件包括温度、湿度和所用的除草剂类型。所述施用率可以在很宽的范围内变化,例如0.001至1.0kg/ha或更多的活性物质,然而优选0.005至750g/ha。
下述实施例举例说明本发明:
A.化学实施例
实施例I-1
在室温下,在30分钟内将在10mlDMF中的1.14克(2.67mmol)前体滴加至8mlDMF和748mg(2.5当量)叔丁醇钾的溶液中,并在此温度下搅拌18小时。然后,将混合物在40℃下加热4小时,减压除去溶剂,并将残余物溶于100ml水中。用1N盐酸将混合物调节至pH=1,过滤所得残余物,得到1.00g(95%)目标化合物A1,为无色油状物。
1H-NMR(400MHz,d6-DMSO):3.33(s,1H,CH2-OCH3),2.04(s,3H,CH3-C≡C)。
类似于实施例I-1并且还根据与制备有关的一般细节,获得以下本发明的化合物。
表1:
nd=未测定
实施例Ia-1
将1.00g(2.6mmol)本发明的化合物(I-11)与在8ml二氯甲烷中的0.5ml三乙胺和1.5mg DMAP一起引入,并在40℃下搅拌10分钟。然后缓慢滴加于2ml二氯甲烷中的0.315g(2.9mmol)氯甲酸乙酯,然后将混合物在40℃下搅拌6小时,然后在室温下过夜。加入10ml碳酸氢钠溶液,分离出有机相。浓缩后剩余的残余物通过柱色谱(硅胶,梯度EtOAc/正庚烷)纯化,得到0.920g(77%)本发明的化合物B1作为异构体混合物。通过在硅胶上的柱色谱(乙酸乙酯/己烷v/v=20:80)得到总计0.43g(47%)无色晶体形式的反式异构体,m.p.183-184℃。
类似于实施例1a-1并根据与制备有关的一般细节,获得以下式(I-1-b)的化合物:
表2:
B.制备实施例(原料)
实施例II-1
将1.10g(4.5mmol)4-环丙基乙烯基-2-乙基-6-甲基苯基乙酸溶于20ml二氯甲烷中并与一滴DMF混合。加入0.75g(1.3eq)草酰氯,将混合物回流加热至沸腾,直至气体停止放出。然后,将反应溶液浓缩,再与每种情况下用20毫升二氯甲烷混合两次,并再次浓缩,以便最后将残余物溶于4ml二氯甲烷(溶液1)中。将1.015(4.5mmol)3-甲氧基甲基环戊烷氨基酸甲酯盐酸盐和1g三乙胺溶于20ml二氯甲烷中,并在90分钟内滴加溶液1。搅拌18小时后,将混合物与50ml水混合,分离出有机相,浓缩并通过柱色谱(硅胶梯度EtOAc/正庚烷)纯化。得到1.16g(62%)所需的目标化合物。
类似于实施例II-1并根据与制备有关的一般细节,获得以下式(II)的化合物:
表3:
实施例(VII-1)
首先将8.41克(32.7mmol)文献中已知的4-溴-2,6-二甲基苯基乙酸甲酯与在45ml三乙胺和18ml吡啶的混合物中的0.1mol%二氯双三苯基二氯化钯一起引入,并加入4.11g(1.9当量)环丙基乙炔。将混合物回流加热至沸腾7.5小时,然后在室温下搅拌过夜。滤出所得的盐,每种情况下用三乙胺和乙醚洗涤两次。将母液减压浓缩,首先与水混合,然后与32ml 3%浓度的盐酸溶液混合。然后,用乙酸乙酯进行萃取,将该有机相用水洗涤2次。干燥有机相后,进行浓缩,所得残余物通过柱色谱(硅胶,梯度正庚烷/乙酸乙酯)纯化。由此得到6.83g(86%)所需的化合物。
1H-NMR(400MHz,CDCl3):7.07(s,2H,Ar-H),3.67(s,5H,OCH3和CH2-Ar),2.26(s,3H,Ar-CH3),1.42(s,1H,CH-c-Pr)
实施例(VII-2)
将7.5g(24.8mmol)2,6-二乙基-4-三甲基甲硅烷基丙炔基苯基乙酸甲酯溶于200ml乙醇中并与4当量氢氧化钾在200ml乙醇中的溶液混合。将混合物回流加热至沸腾7小时,除去溶剂,加入500ml水。然后用盐酸调节pH值为1,每种情况下用100ml乙酸乙酯萃取混合物三次。将合并的有机相用硫酸钠干燥,浓缩并通过柱色谱(硅胶,梯度EtOAc/正庚烷)纯化。由此得到4.3g本发明的化合物(VII-2)。
1H-NMR(400MHz,CDCl3):7.09和7.07,均为s,1H,Ar-H),3.70(s,2H,CH2-Ar),2.62(q,2H,Ar-CH2),2.29(s,3H,Ar-CH3),2.03(s,3H,CH3-C≡C),1.18(t,3H,CH3 -CH2-Ar)
类似地获得以下化合物
表4:
所选实施例的NMR数据
NMR峰列表方法
所选实施例的1H NMR数据以1H NMR峰列表的形式来说明。对于每个信号峰,首先列出δ值(以ppm计),再列出括号中的信号强度。不同信号峰的δ-信号强度值对用分号彼此分隔。
因此,峰列表的一个实例采用如下形式:
δ1(强度1);δ2(强度2);……;δi(强度i);……;δn(强度n)
在NMR谱的打印实例中,尖峰信号的强度与信号高度(以cm计)相关,并显示出信号强度的真实比率。对于宽峰信号,可显示出信号的几个峰或该信号的中值及其与谱中的最强的信号相比的相对强度。
为了校准1H NMR谱的化学位移,使用四甲基硅烷和/或溶剂的化学位移,特别是在DMSO中测量的光谱的情况下。因此,四甲基硅烷峰可能但不需要出现在NMR峰列表中。
1H NMR峰的列表与常规1H NMR输出相似,因此通常包括常规NMR解析所列举的所有峰。
此外,与常规的1H NMR输出相似,其可显示出溶剂信号、目标化合物的立体异构体—其也构成本发明主题的一部分—的信号和/或杂质峰。
在溶剂和/或水的δ范围内出现化合物信号时,1H NMR峰列表示出了常用的溶剂峰,例如DMSO(以DMSO-D6计)峰和水峰,其通常具有较高的平均强度。
目标化合物的立体异构体的峰和/或杂质峰与目标化合物(例如纯度>90%)的峰相比,通常具有较低的平均强度。
这样的立体异构体和/或杂质可能是特定的制备方法所特有的。因此,它们的峰可参照“副产物指纹”来帮助确定我们的制备方法的再现性。
技术人员通过已知方法(MestreC、ACD模拟,以及经验评估的预期值)计算目标化合物的峰可根据需要任选地使用另外的强度滤波器分离出目标化合物的峰。此分离与在常规1H NMR解析中相关的峰值拾取相似。
1H NMR峰值列表的其他细节可以在研究公开数据库(Research DisclosureDatabase)第564025号中找到。
C.制剂实施例
a)粉剂产品通过下述过程获得:将10重量份的通式(I)的化合物和/或其盐与90重量份的作为惰性物质的滑石混合,并将混合物在冲击锤磨机(impact mill)中粉碎。
b)易分散于水中的可湿性粉剂通过下述过程获得:将25重量份的通式(I)的化合物和/或其盐与64重量份的作为惰性物质的含高岭土的石英、10重量份的木素磺酸钾和1重量份的作为润湿剂和分散剂的油酰基甲基牛磺酸钠混合,将混合物在销盘式研磨机(pinned-disk mill)中研磨。
c)易分散于水中的分散浓缩剂通过下述过程获得:将20重量份的通式(I)的化合物和/或其盐与6重量份的烷基苯酚聚乙二醇醚(X207)、3重量份的异十三烷醇聚乙二醇醚(8EO)和71重量份的石蜡矿物油(沸程为例如约255℃至高于277℃)混合,并将混合物在球磨机(attrition ball mill)中研磨至低于5微米的细度。
d)乳油由将15重量份的通式(I)的化合物和/或其盐、75重量份的作为溶剂的环己酮和10重量份的作为乳化剂的氧乙基化的壬基酚混合获得。
e)水分散性颗粒剂通过下述过程获得:使下述物质混合
75重量份通式(I)的化合物和/或其盐,
10重量份木素磺酸钙,
5重量份十二烷基硫酸钠,
3重量份聚乙烯醇,和
7重量份高岭土,
然后将混合物在销盘式研磨机中研磨,并在流化床中通过喷洒施用作为制粒液的水而粒化该粉末。
f)水分散性颗粒剂通过下述过程获得:将下述物质在胶磨机中均化并预粉碎:
25重量份通式(I)的化合物和/或其盐,
5重量份2,2’-二萘基甲烷-6,6’-二磺酸钠,
2重量份油酰基甲基牛磺酸钠,
1重量份聚乙烯醇,
17重量份碳酸钙,和
50重量份水,
随后将混合物在球磨机中研磨,并将所得悬浮液在喷雾塔中通过单料喷嘴进行喷雾并干燥。
D.生物数据
1.出苗前除草作用和作物植物相容性
将单子叶和双子叶禾本科植物和作物植物的种子置于木质纤维盆中的砂壤土中,并用土壤覆盖。将配制为可湿性粉剂(WP)或乳油(EC)形式的本发明的化合物作为水性悬浮液或乳液以600至800l/ha(经换算)的水施用率并加入0.2%的润湿剂施用至覆盖土壤的表面。
处理后,将盆放置在温室中并保持在测试植物的良好生长条件下。在3周的测试期之后,通过与未处理的对照组比较,目测评估对测试植物的损害(以百分比(%)表示的除草作用:100%活性=植物已经死亡,0%活性=对照植物)。
不想要的植物/杂草:
ALOMY:大穗看麦娘 SETVI:狗尾草
AMARE:反枝苋(Amaranthusretroflexus) AVEFA:野燕麦
CYPES:油莎草(Cyperusesculentus) ECHCG:稗草
LOLMU:多花黑麦草 STEME:繁缕(Stellaria media)
VERPE:阿拉伯婆婆纳(Veronica persica) VIOTR:三色堇(Viola tricolor)
POLCO:卷茎蓼(Polygonum convolvulus)
表5:出苗前效力
表6:出苗前效力
表5和表6的结果显示,本发明的化合物对广谱的杂草和禾本科杂草具有良好的出苗前除草效力。例如,化合物编号I-1、I-2、I-5、I-9、I-10、I-11、I-12、I-14、Ia-1、Ia-2、Ia-3、Ia-5、Ia-6、Ia-8、Ia-9、Ia-10、Ia-11、Ia-12、Ia-13和Ia-14,并且在320g/ha的施用率下各自表现出80-100%的抗大穗看麦娘、野燕麦、稗草、多花黑麦草和狗尾草的活性。相比之下,化合物I-7、I-8、I-13、Ia-4和Ia-16在320g/ha施用率下各自表现出80-100%的抗大穗看麦娘、稗草、多花黑麦草和狗尾草的活性。因此,本发明的化合物适于通过出苗前方法防治不想要的植物生长。
2.出苗后除草作用和作物植物相容性
将单子叶和双子叶杂草和作物植物的种子置于木质纤维盆中的沙壤土中,用土壤覆盖并在温室中于良好生长条件下培养。在播种2至3周后,在一叶阶段处理该测试植物。然后将配制为可湿性粉剂(WP)或乳油(EC)形式的本发明的化合物作为水性悬浮液或乳液以600至800l/ha(经换算)的水施用率并添加0.2%的润湿剂喷洒在植物的绿色部位。将测试植物在温室中于最佳生长条件下保持约3周后,与未处理的对照组相比较,目测评估制剂的活性(以百分比(%)表示的除草作用:100%活性=植物已经死亡,0%活性=对照植物)。
表7:出苗后效力
表8:出苗后效力
表7和8的结果显示,本发明的化合物对广谱的禾本科杂草和杂草具有良好的出苗后效力。例如,化合物编号I-1、I-2、I-5、I-7、I-8、I-9、I-10、I-11、I-12、I-13、I-14、Ia-3、Ia-6、Ia-7、Ia-8、Ia-9、Ia-11和Ia-12,并且在80g/ha施用率下各自表现出80-100%的抗大穗看麦娘、稗草、多花黑麦草和狗尾草的活性。因此,本发明的化合物适于通过出苗后方法来防治不想要的植物生长。
如下表所示,与最接近的现有技术(WO 2015/040114,化合物42.03)相比,本发明的化合物在出苗前和出苗后具有改进的除草作用。
表9:出苗前效力的比较数据
表10:出苗后效力的比较数据
Claims (19)
2.根据权利要求1所述的通式(I)的化合物或其农业化学上可接受的盐,其中X和Y各自彼此独立地为甲基或乙基。
3.根据权利要求1或2所述的通式(I)的化合物或其农业化学上可接受的盐,其中R1=甲基或环丙基。
6.根据权利要求1所述的通式(I)的化合物或其农业化学上可接受的盐,其中
X=甲基或乙基,
Y=甲基或乙基,
R1=甲基或环丙基,且
R3=CH3CH2OCH2-或CH3OCH2-。
7.根据权利要求1所述的通式(I)的化合物或其农业化学上可接受的盐,其中X=甲基且Y=乙基。
9.包含根据权利要求1至8之一所述的通式(I)的化合物或其农业化学上可接受的盐以及任选的农业化学上可接受的载体、稀释剂和/或溶剂的除草剂组合物。
10.根据权利要求9所述的除草剂组合物,其包含至少一种选自杀昆虫剂、杀螨剂、除草剂、杀真菌剂、安全剂和生长调节剂的其他农药活性物质。
11.根据权利要求10所述的除草剂组合物,其包含安全剂。
12.根据权利要求9至11之一所述的除草剂组合物,其包含其他除草剂。
13.防治不想要的植物生长的方法,其中将根据权利要求1至8之一所述的化合物施用至待防治的植物、植物部位、植物种子或不想要的植物生长的区域。
14.根据权利要求13所述的方法,其中不想要的植物生长选自禾本科单子叶杂草。
15.根据权利要求13或14所述的方法,其中防治有用植物中耐杂草的植物生长,并且其中将根据权利要求1至8之一所述的化合物施用至待防治的杂草。
16.根据权利要求15所述的方法,其中有用的植物选自小麦、大麦、黑麦、燕麦、稻、甘蔗、大豆、油菜籽、向日葵和玉米。
17.根据权利要求1至8之一所述的通式(I)的化合物或其农业化学上可接受的盐用于防治有害植物的用途。
18.根据权利要求17的用途,其特征在于将通式(I)的化合物或其农业化学上可接受的盐用于防治有用植物作物中的有害植物。
19.根据权利要求18的用途,其特征在于有用植物为转基因有用植物。
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CN110214183A (zh) | 2016-08-03 | 2019-09-06 | 哈佛大学的校长及成员们 | 腺苷核碱基编辑器及其用途 |
US10745677B2 (en) | 2016-12-23 | 2020-08-18 | President And Fellows Of Harvard College | Editing of CCR5 receptor gene to protect against HIV infection |
EP3592853A1 (en) | 2017-03-09 | 2020-01-15 | President and Fellows of Harvard College | Suppression of pain by gene editing |
US10743535B2 (en) | 2017-08-18 | 2020-08-18 | H&K Solutions Llc | Insecticide for flight-capable pests |
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AU2020242662A1 (en) * | 2019-03-15 | 2021-10-07 | Bayer Aktiengesellschaft | Specifically substituted 3-phenyl-5-spirocyclopentyl-3-pyrrolin-2-ones and their use as herbicides |
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US20210024465A1 (en) | 2021-01-28 |
AU2020205345A1 (en) | 2020-08-06 |
ES2730523T3 (es) | 2019-11-11 |
AU2016282731A1 (en) | 2018-02-01 |
TWI706933B (zh) | 2020-10-11 |
TW201718486A (zh) | 2017-06-01 |
UA120656C2 (uk) | 2020-01-10 |
EA201890109A1 (ru) | 2018-07-31 |
KR20180019209A (ko) | 2018-02-23 |
JP2018521045A (ja) | 2018-08-02 |
BR112017028008B1 (pt) | 2022-07-12 |
WO2016207097A1 (de) | 2016-12-29 |
AR105086A1 (es) | 2017-09-06 |
EP3310759A1 (de) | 2018-04-25 |
JP6796088B2 (ja) | 2020-12-02 |
US20180170872A1 (en) | 2018-06-21 |
AU2020205345B2 (en) | 2021-05-13 |
UY36743A (es) | 2017-01-31 |
EP3310759B1 (de) | 2019-03-20 |
CN112159321A (zh) | 2021-01-01 |
US10899709B2 (en) | 2021-01-26 |
AU2016282731B2 (en) | 2020-07-02 |
PL3310759T3 (pl) | 2019-09-30 |
BR112017028008A2 (pt) | 2018-08-28 |
EA035579B1 (ru) | 2020-07-09 |
CA2990078A1 (en) | 2016-12-29 |
CN107922333A (zh) | 2018-04-17 |
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