TW201718486A - 新穎之經炔基取代之３－苯基吡咯啶－２，４－二酮及其作為除草劑之用途 - Google Patents
新穎之經炔基取代之３－苯基吡咯啶－２，４－二酮及其作為除草劑之用途 Download PDFInfo
- Publication number
- TW201718486A TW201718486A TW105119256A TW105119256A TW201718486A TW 201718486 A TW201718486 A TW 201718486A TW 105119256 A TW105119256 A TW 105119256A TW 105119256 A TW105119256 A TW 105119256A TW 201718486 A TW201718486 A TW 201718486A
- Authority
- TW
- Taiwan
- Prior art keywords
- alkyl
- methyl
- compound
- formula
- ethyl
- Prior art date
Links
- 239000004009 herbicide Substances 0.000 title claims description 50
- DLDSFSKURFXLIB-UHFFFAOYSA-N 3-phenylpyrrolidine-2,4-dione Chemical class O=C1CNC(=O)C1C1=CC=CC=C1 DLDSFSKURFXLIB-UHFFFAOYSA-N 0.000 title abstract description 3
- 241000196324 Embryophyta Species 0.000 claims abstract description 104
- 150000001875 compounds Chemical class 0.000 claims abstract description 94
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 35
- 150000003839 salts Chemical class 0.000 claims abstract description 24
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000001768 cations Chemical class 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- 239000001301 oxygen Substances 0.000 claims abstract description 7
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract description 6
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 46
- -1 C 1 -C 4 -alkyl Chemical group 0.000 claims description 38
- 230000002363 herbicidal effect Effects 0.000 claims description 35
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
- 244000038559 crop plants Species 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 24
- 239000004480 active ingredient Substances 0.000 claims description 20
- 108090000623 proteins and genes Proteins 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 13
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
- 230000012010 growth Effects 0.000 claims description 9
- 230000008635 plant growth Effects 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims description 6
- 244000075850 Avena orientalis Species 0.000 claims description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- 239000002917 insecticide Substances 0.000 claims description 6
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 6
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2,5-dimethylpyridine Chemical compound CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 5
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Chemical group 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 150000002500 ions Chemical class 0.000 claims description 5
- 239000011777 magnesium Substances 0.000 claims description 5
- 229910052749 magnesium Inorganic materials 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 238000012546 transfer Methods 0.000 claims description 5
- JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 claims description 4
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 4
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 claims description 4
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- 235000021307 Triticum Nutrition 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- 239000011575 calcium Substances 0.000 claims description 4
- 239000000417 fungicide Substances 0.000 claims description 4
- 239000003630 growth substance Substances 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 4
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 claims description 3
- YCWRLBFFWYMHAQ-UHFFFAOYSA-N 1-phenylpyrrolidine-2,4-dione Chemical class O=C1CC(=O)CN1C1=CC=CC=C1 YCWRLBFFWYMHAQ-UHFFFAOYSA-N 0.000 claims description 3
- PROMNBAYJHEBOK-UHFFFAOYSA-N 2-(2,6-dimethyl-4-prop-2-ynylphenyl)acetic acid Chemical compound CC1=C(C(=CC(=C1)CC#C)C)CC(=O)O PROMNBAYJHEBOK-UHFFFAOYSA-N 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 241000209056 Secale Species 0.000 claims description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 3
- 230000000895 acaricidal effect Effects 0.000 claims description 3
- 239000000642 acaricide Substances 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 229910052791 calcium Inorganic materials 0.000 claims description 3
- 235000005822 corn Nutrition 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 229960003424 phenylacetic acid Drugs 0.000 claims description 3
- 239000003279 phenylacetic acid Substances 0.000 claims description 3
- 150000003222 pyridines Chemical class 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 229910001428 transition metal ion Inorganic materials 0.000 claims description 3
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 2
- NTSLROIKFLNUIJ-UHFFFAOYSA-N 5-Ethyl-2-methylpyridine Chemical compound CCC1=CC=C(C)N=C1 NTSLROIKFLNUIJ-UHFFFAOYSA-N 0.000 claims description 2
- KNCHDRLWPAKSII-UHFFFAOYSA-N 5-ethyl-2-methylpyridine Natural products CCC1=CC=NC(C)=C1 KNCHDRLWPAKSII-UHFFFAOYSA-N 0.000 claims description 2
- 235000007319 Avena orientalis Nutrition 0.000 claims description 2
- 235000014698 Brassica juncea var multisecta Nutrition 0.000 claims description 2
- 235000006008 Brassica napus var napus Nutrition 0.000 claims description 2
- 240000000385 Brassica napus var. napus Species 0.000 claims description 2
- 235000006618 Brassica rapa subsp oleifera Nutrition 0.000 claims description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 claims description 2
- 235000010469 Glycine max Nutrition 0.000 claims description 2
- 244000068988 Glycine max Species 0.000 claims description 2
- 240000005979 Hordeum vulgare Species 0.000 claims description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 claims description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 2
- 235000007164 Oryza sativa Nutrition 0.000 claims description 2
- 240000000111 Saccharum officinarum Species 0.000 claims description 2
- 235000007201 Saccharum officinarum Nutrition 0.000 claims description 2
- 235000007238 Secale cereale Nutrition 0.000 claims description 2
- 229910001424 calcium ion Inorganic materials 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000012973 diazabicyclooctane Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 2
- 235000009566 rice Nutrition 0.000 claims description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 2
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 2
- HVVRUQBMAZRKPJ-UHFFFAOYSA-N 1,3-dimethylimidazolium Chemical compound CN1C=C[N+](C)=C1 HVVRUQBMAZRKPJ-UHFFFAOYSA-N 0.000 claims 1
- 206010010144 Completed suicide Diseases 0.000 claims 1
- 244000020551 Helianthus annuus Species 0.000 claims 1
- 235000003222 Helianthus annuus Nutrition 0.000 claims 1
- 240000007594 Oryza sativa Species 0.000 claims 1
- 244000098338 Triticum aestivum Species 0.000 claims 1
- 240000008042 Zea mays Species 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000002091 cationic group Chemical group 0.000 claims 1
- 229940125782 compound 2 Drugs 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 239000001307 helium Substances 0.000 claims 1
- 229910052734 helium Inorganic materials 0.000 claims 1
- 229910001425 magnesium ion Inorganic materials 0.000 claims 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims 1
- 230000000361 pesticidal effect Effects 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- 241000209504 Poaceae Species 0.000 abstract 1
- 244000045561 useful plants Species 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 230000000694 effects Effects 0.000 description 17
- 238000009472 formulation Methods 0.000 description 16
- 239000000243 solution Substances 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- 235000019439 ethyl acetate Nutrition 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 239000004563 wettable powder Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- 239000004495 emulsifiable concentrate Substances 0.000 description 9
- 239000002689 soil Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000008187 granular material Substances 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 239000004562 water dispersible granule Substances 0.000 description 6
- 241001621841 Alopecurus myosuroides Species 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 230000035784 germination Effects 0.000 description 5
- 238000000227 grinding Methods 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 230000009261 transgenic effect Effects 0.000 description 5
- 239000005995 Aluminium silicate Substances 0.000 description 4
- 241001666377 Apera Species 0.000 description 4
- 108091026890 Coding region Proteins 0.000 description 4
- 244000058871 Echinochloa crus-galli Species 0.000 description 4
- 244000100545 Lolium multiflorum Species 0.000 description 4
- 241000209117 Panicum Species 0.000 description 4
- 235000011999 Panicum crusgalli Nutrition 0.000 description 4
- 235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 4
- 235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 240000003461 Setaria viridis Species 0.000 description 4
- 235000002248 Setaria viridis Nutrition 0.000 description 4
- 241000209072 Sorghum Species 0.000 description 4
- 229940100389 Sulfonylurea Drugs 0.000 description 4
- 241000209149 Zea Species 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 235000012211 aluminium silicate Nutrition 0.000 description 4
- 235000001014 amino acid Nutrition 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000001276 controlling effect Effects 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000000428 dust Substances 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000003337 fertilizer Substances 0.000 description 4
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 4
- 108020004707 nucleic acids Proteins 0.000 description 4
- 102000039446 nucleic acids Human genes 0.000 description 4
- 150000007523 nucleic acids Chemical class 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 230000001105 regulatory effect Effects 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical compound OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 241000743985 Alopecurus Species 0.000 description 3
- 235000005781 Avena Nutrition 0.000 description 3
- 241000209764 Avena fatua Species 0.000 description 3
- 235000007320 Avena fatua Nutrition 0.000 description 3
- 241000611157 Brachiaria Species 0.000 description 3
- 241000209200 Bromus Species 0.000 description 3
- 108020004414 DNA Proteins 0.000 description 3
- 235000017896 Digitaria Nutrition 0.000 description 3
- 241001303487 Digitaria <clam> Species 0.000 description 3
- 241000192043 Echinochloa Species 0.000 description 3
- 241000044408 Eriochloa Species 0.000 description 3
- 241000219146 Gossypium Species 0.000 description 3
- 241000207783 Ipomoea Species 0.000 description 3
- 241000209510 Liliopsida Species 0.000 description 3
- 241000209082 Lolium Species 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 108091028043 Nucleic acid sequence Proteins 0.000 description 3
- 241000745991 Phalaris Species 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 235000005775 Setaria Nutrition 0.000 description 3
- 241000232088 Setaria <nematode> Species 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 238000005054 agglomeration Methods 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 239000000084 colloidal system Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 241001233957 eudicotyledons Species 0.000 description 3
- 230000001747 exhibiting effect Effects 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- 239000012634 fragment Substances 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 230000004060 metabolic process Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 238000001694 spray drying Methods 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 229940104261 taurate Drugs 0.000 description 3
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 3
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 2
- NUPJIGQFXCQJBK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-5-(methoxymethyl)nicotinic acid Chemical compound OC(=O)C1=CC(COC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 NUPJIGQFXCQJBK-UHFFFAOYSA-N 0.000 description 2
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 2
- 108010020183 3-phosphoshikimate 1-carboxyvinyltransferase Proteins 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- 241000743339 Agrostis Species 0.000 description 2
- 241000219318 Amaranthus Species 0.000 description 2
- 235000011331 Brassica Nutrition 0.000 description 2
- 241000219198 Brassica Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241000209120 Cenchrus Species 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 102000053602 DNA Human genes 0.000 description 2
- 235000007351 Eleusine Nutrition 0.000 description 2
- 241000209215 Eleusine Species 0.000 description 2
- 239000005561 Glufosinate Substances 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 239000005566 Imazamox Substances 0.000 description 2
- 235000021506 Ipomoea Nutrition 0.000 description 2
- 241000320639 Leptochloa Species 0.000 description 2
- 241000227653 Lycopersicon Species 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 241000209094 Oryza Species 0.000 description 2
- 231100000674 Phytotoxicity Toxicity 0.000 description 2
- 241000219843 Pisum Species 0.000 description 2
- 241000209048 Poa Species 0.000 description 2
- 241000857233 Rottboellia Species 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 235000002634 Solanum Nutrition 0.000 description 2
- 241000207763 Solanum Species 0.000 description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 2
- 229920002522 Wood fibre Polymers 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 230000000692 anti-sense effect Effects 0.000 description 2
- 239000004490 capsule suspension Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 244000037671 genetically modified crops Species 0.000 description 2
- 238000003306 harvesting Methods 0.000 description 2
- 239000003906 humectant Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000002563 ionic surfactant Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 230000035772 mutation Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 210000003463 organelle Anatomy 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 235000018102 proteins Nutrition 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 239000004546 suspension concentrate Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 239000002025 wood fiber Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 1
- UATLOISVRVAMHZ-UHFFFAOYSA-N 2-[4-(2-cyclopropylethynyl)-2-ethyl-6-methylphenyl]acetic acid Chemical compound C1(CC1)C#CC1=CC(=C(C(=C1)C)CC(=O)O)CC UATLOISVRVAMHZ-UHFFFAOYSA-N 0.000 description 1
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- PRZRAMLXTKZUHF-UHFFFAOYSA-N 5-oxo-n-sulfonyl-4h-triazole-1-carboxamide Chemical compound O=S(=O)=NC(=O)N1N=NCC1=O PRZRAMLXTKZUHF-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000219144 Abutilon Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000209758 Aegilops Species 0.000 description 1
- 241000209136 Agropyron Species 0.000 description 1
- 241000234282 Allium Species 0.000 description 1
- 244000099147 Ananas comosus Species 0.000 description 1
- 241001547866 Anoda Species 0.000 description 1
- 241000404028 Anthemis Species 0.000 description 1
- 241000581616 Aphanes Species 0.000 description 1
- 241001600407 Aphis <genus> Species 0.000 description 1
- 235000003911 Arachis Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000003826 Artemisia Nutrition 0.000 description 1
- 235000003261 Artemisia vulgaris Nutrition 0.000 description 1
- 240000006891 Artemisia vulgaris Species 0.000 description 1
- 235000005340 Asparagus officinalis Nutrition 0.000 description 1
- 241000219305 Atriplex Species 0.000 description 1
- 235000004535 Avena sterilis Nutrition 0.000 description 1
- 241001647031 Avena sterilis Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000132028 Bellis Species 0.000 description 1
- 241000143476 Bidens Species 0.000 description 1
- 241000339490 Brachyachne Species 0.000 description 1
- ZOGDSYNXUXQGHF-XIEYBQDHSA-N Butroxydim Chemical compound CCCC(=O)C1=C(C)C=C(C)C(C2CC(=O)C(\C(CC)=N\OCC)=C(O)C2)=C1C ZOGDSYNXUXQGHF-XIEYBQDHSA-N 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical group [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- 241000220244 Capsella <angiosperm> Species 0.000 description 1
- 241000320316 Carduus Species 0.000 description 1
- 102000053642 Catalytic RNA Human genes 0.000 description 1
- 108090000994 Catalytic RNA Proteins 0.000 description 1
- 241000132570 Centaurea Species 0.000 description 1
- 241000219312 Chenopodium Species 0.000 description 1
- 235000000509 Chenopodium ambrosioides Nutrition 0.000 description 1
- 244000098897 Chenopodium botrys Species 0.000 description 1
- 235000005490 Chenopodium botrys Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 244000192528 Chrysanthemum parthenium Species 0.000 description 1
- 244000037364 Cinnamomum aromaticum Species 0.000 description 1
- 235000014489 Cinnamomum aromaticum Nutrition 0.000 description 1
- 241000132536 Cirsium Species 0.000 description 1
- 239000005497 Clethodim Substances 0.000 description 1
- 241000233838 Commelina Species 0.000 description 1
- 241000207892 Convolvulus Species 0.000 description 1
- 235000009917 Crataegus X brevipes Nutrition 0.000 description 1
- 235000013204 Crataegus X haemacarpa Nutrition 0.000 description 1
- 235000009685 Crataegus X maligna Nutrition 0.000 description 1
- 235000009444 Crataegus X rubrocarnea Nutrition 0.000 description 1
- 235000009486 Crataegus bullatus Nutrition 0.000 description 1
- 235000017181 Crataegus chrysocarpa Nutrition 0.000 description 1
- 235000009682 Crataegus limnophila Nutrition 0.000 description 1
- 235000004423 Crataegus monogyna Nutrition 0.000 description 1
- 240000000171 Crataegus monogyna Species 0.000 description 1
- 235000002313 Crataegus paludosa Nutrition 0.000 description 1
- 235000009840 Crataegus x incaedua Nutrition 0.000 description 1
- 235000010071 Cucumis prophetarum Nutrition 0.000 description 1
- 244000024469 Cucumis prophetarum Species 0.000 description 1
- 241000219122 Cucurbita Species 0.000 description 1
- 239000005501 Cycloxydim Substances 0.000 description 1
- 239000005502 Cyhalofop-butyl Substances 0.000 description 1
- TYIYMOAHACZAMQ-CQSZACIVSA-N Cyhalofop-butyl Chemical group C1=CC(O[C@H](C)C(=O)OCCCC)=CC=C1OC1=CC=C(C#N)C=C1F TYIYMOAHACZAMQ-CQSZACIVSA-N 0.000 description 1
- 241000234653 Cyperus Species 0.000 description 1
- 102000002004 Cytochrome P-450 Enzyme System Human genes 0.000 description 1
- 108010015742 Cytochrome P-450 Enzyme System Proteins 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- 241000320605 Dactyloctenium Species 0.000 description 1
- 241000238578 Daphnia Species 0.000 description 1
- 241000208296 Datura Species 0.000 description 1
- 241000208175 Daucus Species 0.000 description 1
- 241000522190 Desmodium Species 0.000 description 1
- 239000005504 Dicamba Substances 0.000 description 1
- YRMLFORXOOIJDR-UHFFFAOYSA-N Dichlormid Chemical compound ClC(Cl)C(=O)N(CC=C)CC=C YRMLFORXOOIJDR-UHFFFAOYSA-N 0.000 description 1
- 235000003664 Digitaria insularis Nutrition 0.000 description 1
- 241000718034 Digitaria insularis Species 0.000 description 1
- 244000152970 Digitaria sanguinalis Species 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- 102000016680 Dioxygenases Human genes 0.000 description 1
- 108010028143 Dioxygenases Proteins 0.000 description 1
- 208000035240 Disease Resistance Diseases 0.000 description 1
- 240000002092 Echinochloa colona Species 0.000 description 1
- 241000202829 Eleocharis Species 0.000 description 1
- 235000014716 Eleusine indica Nutrition 0.000 description 1
- 244000025670 Eleusine indica Species 0.000 description 1
- 241000744304 Elymus Species 0.000 description 1
- 235000006369 Emex spinosa Nutrition 0.000 description 1
- 244000294661 Emex spinosa Species 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 241001518935 Eragrostis Species 0.000 description 1
- 241000919496 Erysimum Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 241000221079 Euphorbia <genus> Species 0.000 description 1
- 241000234642 Festuca Species 0.000 description 1
- 241001290564 Fimbristylis Species 0.000 description 1
- 239000005529 Florasulam Substances 0.000 description 1
- QZXATCCPQKOEIH-UHFFFAOYSA-N Florasulam Chemical compound N=1N2C(OC)=NC=C(F)C2=NC=1S(=O)(=O)NC1=C(F)C=CC=C1F QZXATCCPQKOEIH-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 101710136180 Galaxin Proteins 0.000 description 1
- 241000816457 Galeopsis Species 0.000 description 1
- 241000748465 Galinsoga Species 0.000 description 1
- 241001101998 Galium Species 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 235000009438 Gossypium Nutrition 0.000 description 1
- 241000208818 Helianthus Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 235000005206 Hibiscus Nutrition 0.000 description 1
- 235000007185 Hibiscus lunariifolius Nutrition 0.000 description 1
- 244000284380 Hibiscus rosa sinensis Species 0.000 description 1
- 241000209219 Hordeum Species 0.000 description 1
- 241000169108 Hydrothrix Species 0.000 description 1
- 240000007171 Imperata cylindrica Species 0.000 description 1
- 241001327265 Ischaemum Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000110847 Kochia Species 0.000 description 1
- 238000005577 Kumada cross-coupling reaction Methods 0.000 description 1
- 241000208822 Lactuca Species 0.000 description 1
- 241000520028 Lamium Species 0.000 description 1
- 241000801118 Lepidium Species 0.000 description 1
- 102000003960 Ligases Human genes 0.000 description 1
- 108090000364 Ligases Proteins 0.000 description 1
- 241000064140 Lindernia Species 0.000 description 1
- 241000208204 Linum Species 0.000 description 1
- 240000004296 Lolium perenne Species 0.000 description 1
- 241000033016 Lolium rigidum Species 0.000 description 1
- 235000002262 Lycopersicon Nutrition 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 235000017945 Matricaria Nutrition 0.000 description 1
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 1
- 235000014435 Mentha Nutrition 0.000 description 1
- 241001072983 Mentha Species 0.000 description 1
- 241000221024 Mercurialis Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 235000003990 Monochoria hastata Nutrition 0.000 description 1
- 240000000178 Monochoria vaginalis Species 0.000 description 1
- 241001442129 Myosotis Species 0.000 description 1
- 241000208125 Nicotiana Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000010676 Ocimum basilicum Nutrition 0.000 description 1
- 240000007926 Ocimum gratissimum Species 0.000 description 1
- 241000069499 Ottochloa Species 0.000 description 1
- 235000015225 Panicum colonum Nutrition 0.000 description 1
- 235000011096 Papaver Nutrition 0.000 description 1
- 240000001090 Papaver somniferum Species 0.000 description 1
- 241001268782 Paspalum dilatatum Species 0.000 description 1
- 241000209046 Pennisetum Species 0.000 description 1
- 244000038248 Pennisetum spicatum Species 0.000 description 1
- 235000007195 Pennisetum typhoides Nutrition 0.000 description 1
- 239000005592 Penoxsulam Substances 0.000 description 1
- SYJGKVOENHZYMQ-UHFFFAOYSA-N Penoxsulam Chemical compound N1=C2C(OC)=CN=C(OC)N2N=C1NS(=O)(=O)C1=C(OCC(F)F)C=CC=C1C(F)(F)F SYJGKVOENHZYMQ-UHFFFAOYSA-N 0.000 description 1
- 241000257649 Phalaris minor Species 0.000 description 1
- 241000461749 Phalaris paradoxa Species 0.000 description 1
- 241000219833 Phaseolus Species 0.000 description 1
- 241000746981 Phleum Species 0.000 description 1
- 239000005597 Pinoxaden Substances 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 241001127637 Plantago Species 0.000 description 1
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000205407 Polygonum Species 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 241000219295 Portulaca Species 0.000 description 1
- 239000005600 Propaquizafop Substances 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-O Pyrazolium Chemical compound C1=CN[NH+]=C1 WTKZEGDFNFYCGP-UHFFFAOYSA-O 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 239000005614 Quizalofop-P-ethyl Substances 0.000 description 1
- 241000218206 Ranunculus Species 0.000 description 1
- 241000220259 Raphanus Species 0.000 description 1
- 241000490453 Rorippa Species 0.000 description 1
- 241000341978 Rotala Species 0.000 description 1
- 241000219053 Rumex Species 0.000 description 1
- 241000209051 Saccharum Species 0.000 description 1
- 240000009132 Sagittaria sagittifolia Species 0.000 description 1
- 241001632050 Salsola Species 0.000 description 1
- 241000202758 Scirpus Species 0.000 description 1
- 241000228160 Secale cereale x Triticum aestivum Species 0.000 description 1
- 241000780602 Senecio Species 0.000 description 1
- 244000275012 Sesbania cannabina Species 0.000 description 1
- 235000017016 Setaria faberi Nutrition 0.000 description 1
- 241001355178 Setaria faberi Species 0.000 description 1
- 235000008515 Setaria glauca Nutrition 0.000 description 1
- CSPPKDPQLUUTND-NBVRZTHBSA-N Sethoxydim Chemical compound CCO\N=C(/CCC)C1=C(O)CC(CC(C)SCC)CC1=O CSPPKDPQLUUTND-NBVRZTHBSA-N 0.000 description 1
- 241000220261 Sinapis Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 241000488874 Sonchus Species 0.000 description 1
- 235000017967 Sphenoclea zeylanica Nutrition 0.000 description 1
- 244000273618 Sphenoclea zeylanica Species 0.000 description 1
- 240000006694 Stellaria media Species 0.000 description 1
- 241000722118 Thlaspi Species 0.000 description 1
- 239000005624 Tralkoxydim Substances 0.000 description 1
- 241000219793 Trifolium Species 0.000 description 1
- 235000019714 Triticale Nutrition 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- 241001521331 Urochloa Species 0.000 description 1
- 241000972221 Urochloa decumbens Species 0.000 description 1
- 241000044594 Urochloa plantaginea Species 0.000 description 1
- 241000219422 Urtica Species 0.000 description 1
- 241000792914 Valeriana Species 0.000 description 1
- 241000219873 Vicia Species 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 241001506766 Xanthium Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- OSWRVYBYIGOAEZ-UHFFFAOYSA-N acetic acid;2-hydroxypropanoic acid Chemical compound CC(O)=O.CC(O)C(O)=O OSWRVYBYIGOAEZ-UHFFFAOYSA-N 0.000 description 1
- 239000012345 acetylating agent Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 244000193174 agave Species 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000002528 anti-freeze Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 235000009052 artemisia Nutrition 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- BYKIXXQPEHRKPP-UHFFFAOYSA-N benzenecarboximidamide 1,2-oxazole Chemical compound C=1C=NOC=1.NC(=N)C1=CC=CC=C1 BYKIXXQPEHRKPP-UHFFFAOYSA-N 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- FUHMZYWBSHTEDZ-UHFFFAOYSA-M bispyribac-sodium Chemical compound [Na+].COC1=CC(OC)=NC(OC=2C(=C(OC=3N=C(OC)C=C(OC)N=3)C=CC=2)C([O-])=O)=N1 FUHMZYWBSHTEDZ-UHFFFAOYSA-M 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229920005551 calcium lignosulfonate Polymers 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
- FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 1
- 229960000623 carbamazepine Drugs 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- GGWHBJGBERXSLL-NBVRZTHBSA-N chembl113137 Chemical compound C1C(=O)C(C(=N/OCC)/CCC)=C(O)CC1C1CSCCC1 GGWHBJGBERXSLL-NBVRZTHBSA-N 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229960003405 ciprofloxacin Drugs 0.000 description 1
- SILSDTWXNBZOGF-JWGBMQLESA-N clethodim Chemical compound CCSC(C)CC1CC(O)=C(C(CC)=NOC\C=C\Cl)C(=O)C1 SILSDTWXNBZOGF-JWGBMQLESA-N 0.000 description 1
- JBDHZKLJNAIJNC-LLVKDONJSA-N clodinafop-propargyl Chemical group C1=CC(O[C@H](C)C(=O)OCC#C)=CC=C1OC1=NC=C(Cl)C=C1F JBDHZKLJNAIJNC-LLVKDONJSA-N 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000012136 culture method Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 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
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 1
- 235000021186 dishes Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- PQKBPHSEKWERTG-LLVKDONJSA-N ethyl (2r)-2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]propanoate Chemical group C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 PQKBPHSEKWERTG-LLVKDONJSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 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
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000009313 farming Methods 0.000 description 1
- 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
- GINFBXXYGUODAT-UHFFFAOYSA-N flucarbazone Chemical compound O=C1N(C)C(OC)=NN1C(=O)NS(=O)(=O)C1=CC=CC=C1OC(F)(F)F GINFBXXYGUODAT-UHFFFAOYSA-N 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 150000002334 glycols Chemical class 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
- COYBRKAVBMYYSF-UHFFFAOYSA-N heptan-2-yl [(5-chloroquinolin-8-yl)oxy]acetate Chemical group C1=CN=C2C(OCC(=O)OC(C)CCCCC)=CC=C(Cl)C2=C1 COYBRKAVBMYYSF-UHFFFAOYSA-N 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 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
- 230000002147 killing effect Effects 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 229940096405 magnesium cation Drugs 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 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
- 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
- 150000004702 methyl esters Chemical class 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000001823 molecular biology technique Methods 0.000 description 1
- 238000010369 molecular cloning Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000002703 mutagenesis Methods 0.000 description 1
- 231100000350 mutagenesis Toxicity 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
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 229920002113 octoxynol Polymers 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- 238000010651 palladium-catalyzed cross coupling reaction Methods 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- JGTNAGYHADQMCM-UHFFFAOYSA-N perfluorobutanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-N 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003090 pesticide formulation Substances 0.000 description 1
- 230000005097 photorespiration Effects 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 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
- 210000002706 plastid Anatomy 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000008569 process Effects 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
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 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
- 238000010188 recombinant method Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 108091092562 ribozyme Proteins 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229930000044 secondary metabolite Natural products 0.000 description 1
- 238000000926 separation method Methods 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
- JRQGDDUXDKCWRF-UHFFFAOYSA-M sodium;n-(2-methoxycarbonylphenyl)sulfonyl-4-methyl-5-oxo-3-propoxy-1,2,4-triazole-1-carboximidate Chemical compound [Na+].O=C1N(C)C(OCCC)=NN1C(=O)[N-]S(=O)(=O)C1=CC=CC=C1C(=O)OC JRQGDDUXDKCWRF-UHFFFAOYSA-M 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011232 storage material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 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
- 150000003852 triazoles Chemical class 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
- NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical group C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
- QGEACRIKUUTESN-UHFFFAOYSA-K tripotassium triacetate Chemical compound [K+].[K+].[K+].CC([O-])=O.CC([O-])=O.CC([O-])=O QGEACRIKUUTESN-UHFFFAOYSA-K 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 235000017468 valeriana Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000004552 water soluble powder 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
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- 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
-
- 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
- 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
-
- 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
-
- 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
本發明係關於新穎有效之根據通式(I)的經炔基取代之3-苯基吡咯啶-2,4-二酮或其農化上可接受的鹽，□其中X=C1-C4-烷基，C1-C4-鹵烷基或C3-C6-環烷基；Y=C1-C4-烷基或C3-C6-環烷基；n=1,2或3；m=1或2；R1=C1-C6-烷基，或C3-C6-環烷基；R2=氫或甲基；R3=C1-C3-烷氧基-C1-C3-烷基，或帶有氧或硫原子的五元或六元雜環；G=氫、一個可切斷的基團L或陽離子E。本發明亦關於根據本發明的化合物用於防治雜草和有用的植株作物中之雜草之用途。
Description
本發明係關於根據通式(I)之新穎有效之經炔基取代的3-苯基吡咯啶-2,4-二酮或其農化上可接受的鹽類，以及其用於防治雜草和有用的植株作物中之雜草的用途。
先前技藝已熟知3-芳基吡咯啶-2,4-二酮類化合物及其製備和作為除草劑的用途。
而且，例如具有除草劑、殺昆蟲劑或殺真菌劑效果的二環的3-芳基吡咯啶-2,4-二酮衍生物(EP-A-355 599,EP-A-415 211和JP-A 12-053 670 ff.)以及經取代的單環3-芳基吡咯啶-2,4-二酮衍生物(EP-A-377 893和EP-A-442 077 ff.)也被說明過。具有除草劑效果之經炔基取代之N-苯基吡咯啶-2,4-二酮亦從WO 96/82395、WO 98/05638、WO 01/74770、WO 14/032702或WO15/040114得知。
這些殺草劑對於有害植物的效果視各種參數而定，例如所使用的施用比例、製備物的形式(調配物)、在每一情形中要防治的有害植物、有害植株的譜系範圍、以及氣候和土壤比率，以及作用時間和/或除草劑的分解速率。為了發展充分
的除草劑效果，各種出自3-芳基吡咯啶-2,4-二酮群組的除草劑需要高的施用比例和/或狹窄的有害植株譜系範圍，這使其施用在經濟學上不具吸引力。因此吾人需要具有改進之性質且在經濟學上具有吸引力且同時有效率的其他除草劑。
因此，本發明的目標是要提供不具有所述缺點的新穎化合物。
因此本發明係關於通式(I)之新穎之經炔基取代之N-苯基吡咯啶-2,4-二酮，
或一種其在農化上可接受的鹽。其中X=C1-C4-烷基、C1-C4-鹵烷基或C3-C6-環烷基，Y=C1-C4-烷基或C3-C6-環烷基，n=1、2或3，m=1或2，R1=C1-C6-烷基，或C3-C6-環烷基，R2=氫或甲基，R3=C1-C3-烷氧基-C1-C3-烷基，或帶有氧或硫原子的五元或六元雜環，G=氫、可切斷的L基團或E陽離子；其中
L=以下基團之一
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、未飽和的苯基或苯基，其被鹵基、C1-C4-烷基、C1-C4-鹵烷基、C1-C4-烷氧基、C1-C4-halo烷氧基、硝基或氰基取代一或多次，R7，R7‘=在每一情形中彼此獨立為甲氧基或乙氧基，R8和R9=在每一情形中彼此獨立為甲基、乙基、苯基或共同形成飽和的五元、六元或七元環，或共同形成帶有氧原子或硫原子的飽和五元、六元或七元雜環，E=鹼金屬離子、鹼土金屬離子、鋁離子或過渡金屬離子、氫鎂陽離子，或銨離子，其中視需要一個、兩個、三個或四個氫原子經完全相同的或相異的出自氫、C1-C5-烷基、C1-C5-烷氧基或C3-C7-環烷基群組的基團取代，在每一情形中經氟、氯、溴、氰基、羥基取代一或多次或被一個或多個氧或硫原子介入，或是環狀的二級或三級脂肪族的或雜脂肪則的胺基離子，例如嗎啉陽離子、硫代嗎啉陽離子、哌啶陽離子、吡咯啶陽離子，或在每一情形中為經過質子化的1,4-二氮雜二環[2.2.2]辛烷(DABCO)或1,5-二氮雜二環[4.3.0]十一-7-烯(DBU)，或雜環銨離子，例如在每一情形中為質子化的吡啶、
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、喹噁啉、1,2-二甲基咪唑、1,3-二甲基咪甲基硫酸鹽，或進而為鋶離子。
本發明之一項通用的定義係以通式(I)提出。本說明書之以上和以下所提化學式中之較佳取代基或基團範圍於之後說明：在式(I)和所有以下的化學式中，具有多於兩個碳原子的烷基可為直鏈的或分支的。烷基為例如甲基、乙基、正-或異丙基、正-、異-、三級-或2-丁基、戊基如正戊基、2,2-二甲基丙基和3-甲基丁基。環烷基是一個具有三到六個碳原子的碳環之飽和環系統，例如環丙基、環丁基、環戊基或環己基。
鹵基是氟、氯、溴或碘。
式(I)化合物可視取代基的形式以幾何的和/或光學異構物或異構物混合物存在於不同的組成物中，視需要可以常見的方式將其分離。本發明提供純粹的異構物以及互變異構物、異構物或鏡像異構物的混合物、其製備和用途，以及包含這些異構物的組成物。然而，簡單起見，本說明書以下所使用的術語是指式(I)化合物，儘管吾人意圖指純化合物和視需要指具有不同比率之異構物與互變異構化合物的混合物。
請參照以下化合物，其中X=C1-C4-烷基或C3-C6-環烷基，Y=C1-C4-烷基或C3-C6-環烷基，n=1、2或3，m=1或2，R1=甲基、乙基、異丙基或環丙基，
R2=氫或甲基，R3=C1-C3-烷氧基-C1-C3-烷基，G=氫、可切斷的L基團或E陽離子；其中L=以下基團之一者
其中R4=C1-C4-烷基，R5=C1-C4-烷基，R6=C1-C4-烷基，未經取代的苯基或經鹵基、C1-C4-烷基或C1-C4-烷氧基取代的苯基，R7、R7‘=彼此獨立的甲氧基或乙氧基，E=鹼金屬離子、鹼土金屬離子、鋁離子或過渡金屬離子、或銨離子，其中視需要一個、兩個、三個或所有四個氫原子被完全相同的或相異的基團取代，該基團係選自氫或C1-C5-烷基，或三級脂肪族或雜脂肪族銨離子，或一個雜環的銨陽離子的群組，例如在每一情形中為經質子化吡啶、喹啉、喹噁啉、1,2-二甲基咪唑、1,3-二甲基咪唑甲基硫酸鹽或亦可為鋶離子，尤佳者當屬以下化合物，其中X=甲基、乙基或環丙基，Y=甲基或乙基，n=1或2，
m=1或2，R1=甲基、乙基、異丙基或環丙基，R2=氫R3=CH3CH2OCH2-或CH3OCH2-，G=氫、可切斷的L基團或E陽離子；其中L=以下基團之一者
其中R4=C1-C4-烷基，R5=C1-C4-烷基，E=鹼金屬離子、鹼土金屬離子、鋁的離子對等物、過渡金屬的離子對等物或鹵化鎂陽離子、四-C1-C5-烷基銨離子或雜環的銨離子，例如在每一情形中為質子化的吡啶或喹啉，或亦可為鋶離子。
非常尤佳者當屬式(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、異丙基或環丙基，R2=氫，R3=CH3CH2OCH2-或CH3OCH2-，G=氫、可切斷的L基團或E陽離子；其中L=以下基團之一者
其中R4=甲基、乙基或異丙基，R5=甲基或乙基，E=鈉、鉀、三甲基銨、吡啶陽離子、喹啉陽離子或三甲基鋶離子或是鈣或鎂的離子對等物。
根據本發明之通式(I)化合物的製備基本上已知和/或可依照文獻中已知的方法來實行，例如藉由
a)將通式(II)的化合物環化
其中X、Y、R1、R2和R3、以及n和m具有以上所給的意義，且R10是烷基，較佳是甲基或乙基，視需要在適當的溶劑或稀釋劑存在下，以適當的鹼以正規方式切下R10OH基團，或
b)將通式(Ia)化合物，
其中X,Y,R1,R2和R3，以及n和m具有以上所給意義者，與通式(III)的化合物反應。
Hal-L (III)
其中L具有以上所給的意義且Hal是鹵基，較佳是氯或溴或可為磺酸基團，視需要在適當的溶劑或稀釋劑還有適當的鹼存在下進行。
(c)將通式(IV)的化合物
其中X、Y、R2和R3，以及m、n和G具有以上所給的意義，且U為適當脫離基者，與通式(V)之適當炔化試劑反應，
其中R3具有以上所給的意義且W為氫或適當的脫離基，視需要於適當的催化劑和適當的鹼存下進行。適當的脫離基W為例如鹵原子如氯、溴或碘，烷基磺酸酯基團，例如：
三氟酸酯、甲磺酸酯或全氟丁基磺酸酯、氯化鎂、氯化鋅、三烷基錫基團，和硼酸基團如B(OH)2或-B(O烷基)2。 Pd0錯合物尤其非常立即適用於作為催化劑，在許多情形中添加Cu(I)鹽是非常有利的。
所說明的方法學是先前技藝中已知的而且在此關聯中也在「鈀催化的交叉耦合」、「薗頭[Sonogashira]、根岸[Negishi]、鈴木[Suzuki]、史蒂利[Stille]或熊田[Kumada]耦合」之關鍵字下。
或者，通式(IV)的化合物亦可與通式(VI)的炔基試劑藉與以上說明耦合方法相似的施行方式反應，然後經切割成為通式(VIII)的乙炔基化合物且最後將這些物質用適當的烷化試劑轉換成根據本發明的式(I)化合物，其中在每一情形中X、Y、R2、R3、n、m、G和W具有所說明的意義且該可切斷的基團R11可為例如(C1-C4-烷基)2C-OH基團。
這項技術同樣在文獻中為已知，在例如《Beilstein Journal of Organic Chemistry》2011,7(55),426-431和在《and Catalysis Communications》，2015,60,82-87中被更詳細解釋。
還有另一技術係包含將通式(IV)的化合物與通式(IX)的炔基試劑以和以上說明之偶合方法相似的施行方式反應。然後，可在適當條件下將R12基團切下，產生根據本發明之式
(I)化合物，其中R3=Me，其中在每一情形裡X、Y、R2、n、m、G和W具有該說明之意義。R12是C1-C4-三烷基矽基。
這項技術是文獻中已知者，說明在例如《Journal of Medicinal Chemistry》2007,50(7),1627-1634。
所需之通式(II)的前驅體
可經已知方法製備，將通式(VI)的胺基酸酯與通式(VII)的苯基乙酸反應，其中X,Y,R1,R2和R3和R10，還有n和m具有以上說明的意義，視需要藉著添加一種脫水劑且視需要在適當的溶劑或稀釋劑存在下進行。
還有一項製備通式(II)之化合物之改變的方法包括例如也是將式(IIa)化合物，其中X,Y,R2,R3,R10,R11,n和m以及U具有以上所給意義者反應，藉由已說明過的交叉偶合法進行。
通式(VII)的苯基乙酸-稱為2,6-二甲基-4-炔丙基苯基乙酸-基本上是在WO 2015/040114被提到，但未說明這些化合物的取得途徑。
然而，其可依照文獻中已知的方法製備，例如藉著將通式(X)的化合物，其中X,Y,U,W,R3,R10和R11如以上定義且R=C1-C4-烷基者與通式(VI)或(V)的試劑反應，其再次使用以上說明過的技術。
根據本發明的式(I)化合物(和/或其鹽)，於以下統稱為「根據本發明的化合物」具有對抗寬廣譜系之經濟上重要之單子葉或雙子葉一年生雜草之優良的除草劑效果。該活性成分亦有效作用在從根莖、根幹和其他多年生器官產生芽且難以防治的多年生雜草。
因此本發明也提供防治不想要的植株或調節植株生長的方法，較佳是在植株作物中，其中一種或多於一種根據本發明的化合物被施用於植株(例如有害植株如單子葉或雙子葉雜草或不想要的作物植株)，種子(例如穀實、種子、營養繁
殖芽如塊莖或帶芽的幼枝部分)或植株生長的區域(例如耕種的區域)。本發明的化合物可在例如播種前(若適當亦可藉著將其併入土壤中)、發芽前或發芽後佈署。吾人特定地藉由實例提出的數種可被根據本發明的化合物防治單子葉或雙子葉的雜草族群，但無意提出名稱來對某些植株種類加以限制。
單子葉之以下屬別的有害植株：山羊草屬(Aegilops)、鵝觀草屬(Agropyron)、剪股穎屬(Agrostis)、看麥娘屬(Alopecurus)、早熟禾(Apera)、野燕麥(Avena)、臂形草屬(Brachiaria)、雀麥屬(Bromus)、蒺蔾草屬(Cenchrus)、鴨跖草屬(Commelina)、狗牙根屬(Cynodon)、莎草屬(Cyperus)、(Dactyloctenium)、馬唐屬(Digitaria)、稗屬(Echinochloa)、荸薺屬(Eleocharis)、槮屬(Eleusine)、畫眉草屬(Eragrostis)、野黍屬(Eriochloa)、羊茅屬(Festuca)、飄拂草屬(Fimbristylis)、異蕊花屬(Heteranthera)、白茅屬(Imperata)、鴨嘴草屬(Ischaemum)、千金子屬(Leptochloa)、毒麥屬(Lolium)、鴨舌草屬(Monochoria)、稷屬(Panicum)、雀稗屬(Paspalum)、鷸草屬(Phalaris)、梯牧草屬(Phleum)、早熟禾屬(Poa)、筒軸茅屬(Rottboellia)、慈姑屬(Sagittaria)、莞屬(Scirpus)、狗尾草屬(Setaria)、高粱(Sorghum)。
雙子葉之以下屬別的雜草：苘麻屬(Abutilon)、莧屬(Amaranthus)、豚草屬(Ambrosia)、錦葵科(Anoda)、春黃菊屬(Anthemis)、薔薇科(Aphanes)、艾屬(Artemisia)、濱藜屬(Atriplex)、雛菊屬(Bellis)、鬼針屬(Bidens)、薺屬(Capsella)、飛廉屬(Carduus)、決明屬(Cassia)、矢車菊屬(Centaurea)、藜屬(Chenopodium)、薊屬(Cirsium)、旋花屬(Convolvulus)、曼陀羅屬(Datura)、山螞蝗屬(Desmodium)、蓼科(Emex)、糖芥屬(Erysimum)、大戟屬(Euphorbia)、鼬瓣花屬(Galeopsis)、小米菊屬(Galinsoga)、拉拉藤屬(Galium)、木槿屬(Hibiscus)、
番薯屬(Ipomoea)、地膚屬(Kochia)、野芝麻屬(Lamium)、獨行菜屬(Lepidium)、母草屬(Lindernia)、母菊屬(Matricaria)、薄荷屬(Mentha)、山靛屬(Mercurialis)、番杏科(Mullugo)、勿忘草屬(Myosotis)、罌粟屬(Papaver)、牽牛花屬(Pharbitis)、車前屬(Plantago)、蓼屬(Polygonum)、馬齒莧屬(Portulaca)、毛莨屬(Ranunculus)、蘿蔔屬(Raphanus)、蔊菜屬(Rorippa)、水豬母乳屬(Rotala)、酸模屬(Rumex)、豬毛菜屬(Salsola)、黃菀屬(Senecio)、田菁屬(Sesbania)、黃花稔屬(Sida)、歐白芥屬(Sinapis)、茄屬(Solanum)、苦苣菜屬(Sonchus)、尖瓣花屬(Sphenoclea)、繁縷屬(Stellaria)、蒲公英(Taraxacum)、遏藍菜屬(Thlaspi)、三葉草屬(Trifolium)、蕁麻(Urtica)、婆婆納屬(Veronica)、堇菜屬(Viola)、蒼耳屬(Xanthium)。
若本發明的化合物在發芽前被施用於土壤表面，雜草幼苗的發芽被完全預防或雜草生長至其達到子葉階段，但其在三到四週過後停止生長並且最終完全死掉。
若是活性成分在發芽後被施用到植株的綠色部分，則在處理之後生長停止，且有害植株在施用時保持在生長階段，或其在某時間之後完全死亡，使得有害於作物植株的雜草之競爭非常早就以延續方式被縮限。
雖然根據本發明的化合物對於單子葉和雙子葉的雜草具有優良的除草活性，而對重要的經濟作物例如雙子葉的以下屬別：花生屬(Arachis)、甜菜(Beta)、芸苔屬(Brassica)、香瓜屬(Cucumis)、南瓜屬(Cucurbita)、向日葵屬(Helianthus)、胡蘿蔔屬(Daucus)、大豆屬(Glycine)、棉屬(Gossypium)、番薯屬(Ipomoea)、萵苣屬(Lactuca)、亞麻屬(Linum)、番茄屬(Lycopersicon)、菸草屬(Nicotiana)、萊豆屬(Phaseolus)、豌豆屬(Pisum)、茄屬(Solanum)、蠶豆屬(Vicia)，或以下屬別的單子葉作物：蔥屬(Allium)、鳳梨屬(Ananas)、天門冬屬(Asparagus)、野燕麥(Avena)、大麥屬(Hordeum)、稻屬(Oryza)、
稷屬(Panicum)、甘蔗屬(Saccharum)、黑麥屬(Secale)、高粱屬(Sorghum)、黑小麥屬(Triticale)、小麥屬(Triticum)、玉蜀黍屬(Zea)，尤其是玉蜀黍屬(Zea)和小麥屬(Triticum)，僅不顯著的受損或完全不受損，是根據本發明的特殊化合物的結構及其施用比例而定。因為這些理由，本發明之化合物非常適用於選擇性的防治作物植株如農業上有用的植株或裝飾用植株中不想要的植株生長。
此外，根據本發明的化合物(視其特殊結構和所配置的施用比例而定)在作物植株具有傑出的生長調節性質。其以調節作用干涉植株本身的代謝，因此可用於受控的影響植株成分和輔助收成，例如藉著乾燥和阻礙生長。還有，其亦適用於一般防治和抑制不想要的植物生長而不殺死該過程中的植株。抑制植物生長在許多單子葉和雙子葉作物中扮演重要的角色，因為例如該貯存物質的形成可因此被降低或完全預防。
因其除草和植物生長調節性質，活性成分亦可用於防治基改植株或藉由傳統突變法修改的植株作物中之有害植株。一般而言，基因轉殖的植株之特徵為其特殊的有利性質，例如對於某些除害蟲劑的抗對性，對於某些除草劑，植物疾病或植物疾病之病原體-如某些昆蟲或微生物如真菌、細菌或病毒的對抗性。其他特殊的性質係關於例如收成物資的收成量、品質、可貯存性、組成和特定成分。例如，具有提高的澱粉含量或經改變之澱粉性質的基因轉殖植株，或收成物資中具有不同的脂肪酸組成的基因轉殖植株。
關於基因轉殖作物，較佳者當屬施用根據本發明的化合物於經濟上重要的有用植株和裝飾用植株之基因轉殖作物，例如穀物如小麥、大麥、裸麥、燕麥、粟米、水稻、樹薯和玉米或其他甘蔗、棉花、大豆、油菜、馬鈴薯、番茄、豌豆和其他蔬菜作物。較佳是本發明的化合物可作為除草劑，用
於能對抗或經遺傳工程改造能對抗除草劑之植物毒性影響的有用植株作物。
與既存植株相較，具有經改進的性質之新穎植株的傳統生產方法包括，例如：傳統培養法和生產突變株。或者，具有經修飾性質之新穎植株可借助重組的方法產生(請參考例如EP-A-0221044、EP-A-0131624)。例如，在以下數種情形中已有說明：- 以達到修改植株中合成澱粉為目的之基因修飾作物植株(例如：WO 92/11376、WO 92/14827、WO 91/19806)，- 能對抗某些固殺草(glufosinate)型(請參考例如EP A-0242236,EP-A-242246)或嘉磷塞型(WO 92/00377)或磺醯基尿素型(EP-A-0257993,US A 5013659)除草劑的基因轉殖作物植株，- 基因轉殖的作物植株，例如棉花，其具有生產蘇力菌毒素的能力，這使植株能對抗特殊的害蟲(EP-A-0142924,EP-A-0193259)，- 具有經修改之脂肪酸組成的基因轉殖的作物植株(WO 91/13972)，- 具有新穎成分或二級代謝物例如新穎的植物抗菌素之基因改造作物植株，該物質能造成增進的疾病對抗力(EPA 309862,EPA0464461)，- 具有降低之光呼吸作用之基改植株，其具有較高產率和較高的壓力耐受性(EPA 0305398)，- 能產生醫藥上或診斷上重要之蛋白質(「分子藥物養殖業」)的基因轉殖作物植株，- 標榜較高產率或較佳品質的基因轉殖的作物植株，- 以先前所提新穎性質之組合為特徵(「基因堆壘」)的基因轉殖作物植株。
基本上已知許多可被用於生產新穎之具備經修改性質之
基因轉殖植株的分子生物學技術，請參考，例如：I.Potrykus and G.Spangenberg(eds.)Gene Transfer to Plants,Springer Lab Manual(1995),Springer Verlag Berlin,Heidelberg，或Christou,"Trends in Plant Science"1(1996)423-431)。
對於此種重組操作，可將容許突變或藉由DNA序列重組使序列改變的核酸分子導入質體中。借助標準方法吾人可以例如進行鹼基交換，移除掉序列之部分或添加天然的或合成的序列。為了將DNA片段一一連接起來，可將轉接序列或連接序列放到該片段中，請參考Sambrook et al.,1989,Molecular Cloning,A Laboratory Manual,2nd edition Cold Spring Harbor Laboratory Press,Cold Spring Harbor,NY，或Winnacker"Gene und Klone[Genes and clones]”,VCH Weinheim 2nd edition 1996。
例如，要想產生具有降低之基因產物活性的植物細胞可藉著表現至少一項對應的反意義股RNA、或表現至少一種適當建立的核糖酶來達成，該核糖酶特定地切斷以上所提基因產物的轉錄片段。為此目的，首先可使用涵蓋基因產物之整個編碼序列(包括任何可能出現的側翼序列)的DNA分子，亦可使用僅涵蓋編碼序列部分的DNA分子，在該情形中這些部分必須長到夠在細胞中具有反意義核酸效應。亦可使用對於基因產物之編碼序列高度同源但非與其完全相同的DNA序列。
將核酸分子在植株中表現時，所合成蛋白質可位在植株細胞之任何所希望的小室中。然而，為了達成使其位在某一胞器中，吾人可以例如將該編碼區與能確保其位在某一小室中的DNA序列連接。此種序列對於熟習本技藝者是已知(請參考例如，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)。核酸分子亦可在
植株細胞的胞器中表現。
該基因轉殖植株的細胞可以藉已知的技術再生成為整株植物。基本上，該基因轉殖植株可為任何想要的植物品種的植株，亦即不僅是單子葉且亦可為雙子葉植株。
因此，可以得到基因轉殖的植株，其性質藉由過度的表達、壓抑或抑制同源的(天然的)基因或基因序列或是表現異源的(外來的)基因或基因序列而被改變。
本發明的化合物可優先使用在能對抗生長調節劑，例如麥草畏(Dicamba)，或能對抗抑制必須植物酵素的除草劑，例如乙醯乳酸合成酶(ALS)、EPSP合成酶、麩醯胺酸合成酶(GS或羥基苯基丙酮酸鹽二氧化化酶(HPPD)，或選自以下群組：磺醯基尿素、嘉磷塞、固殺草(glufosinate)或苯甲醯基異噁唑類之除草劑和相似活性成分的基因轉殖作物。
當本發明的活性成分被用於基因轉殖作物時，不僅對於在其他作物中觀察到之有害植株的影響被觀察到，而且也經常觀察到特定於施用在特殊基因轉殖作物的影響，例如經改變的或特定放大的可被防治之雜草範圍、經改變之可被使用的施用比例，較佳是與基因轉殖作物能對抗的除草劑有良好的相容性，以及影響基因轉殖的作物植株的生長和產率。
因此本發明也提供本發明的化合物作為除草劑以防治基因轉殖的作物植株中之有害植株的用途。
在本發明之一項較佳實例中，通式(I)的化合物可被用於防治那些有害植株，例如出自以下群組的植株：剪股穎屬(Agrostis)、看麥娘屬(Alopecurus)、早熟禾(Apera)、野燕麥(Avena)、臂形草屬(Brachiaria)、雀麥屬(Bromus)、蒺蔾草屬(Cenchrus)、馬唐屬(Digitaria)、稗屬(Echinochloa)、槮屬(Eleusine)、野黍屬(Eriochloa)、千金子屬(Leptochloa)、毒麥屬(Lolium)、奧圖草屬(Ottochloa)、稷屬(Panicum)、狼尾草屬(Pennisetum)、鷸草屬(Phalaris)、早熟禾屬(Poa)、筒軸
茅屬(Rottboellia)、狗尾草屬(Setaria)和/或高粱屬(Sorghum)雜草；尤其是看麥娘屬(Alopecurus)、早熟禾(Apera)、野燕麥(Avena)、臂形草屬(Brachiaria)、雀麥屬(Bromus)、馬唐屬(Digitaria)、稗屬(Echinochloa)、野黍屬(Eriochloa)、毒麥屬(Lolium)、稷屬(Panicum)、鷸草屬(Phalaris)、早熟禾屬(Poa)、狗尾草屬(Setaria)和/或高粱屬(Sorghum)雜草，-其對一種或多於一種能抑制乙醯基-CoA-羧酸酯酶(ACCase)的除草劑具有抗藥性。能抑制ACCase的殺草劑為尤其是唑啉草酯(pinoxaden)、炔草酯(clodinafop-propargyl)、精惡唑禾草靈(fenoxaprop-P-ethyl)、克硫松(diclofop-methyl)、伏寄普(fluazifop-P-butyl)、甲基合氯氟(haloxyfop-P-methyl)、快伏草(quizalofop-P-ethyl)、普拔草(propaquizafop)、丁基賽伏草(cyhalofop-butyl)、剋草同(clethodim)、西殺草(sethoxydim)、環殺草(cycloxydim)、苯草酮(tralkoxydim)或丁苯草酮(butroxydim)；- 和/或對嘉磷塞具有抗藥性，- 和/或對一種或多於一種能抑制乙醯乳酸鹽合成酶(ALS)的除草劑具有抗藥性，例如一種或多於一種磺醯基尿素除草劑，例如碘甲磺隆(iodosulphurone-methyl)、甲基二磺隆(mesosulphurone-methyl)、苯磺隆(tribenuron-methyl)、醚苯磺隆(triasulphurone)、氟磺隆(prosulphurone)、磺醯磺隆(sulphosulphurone)、百速隆(pyrazosulphurone-ethyl)、免速隆(bensulphurone-methyl)、菸嘧磺隆(nicosulphurone)、氟速隆(flazasulphurone)、iofensulphurone、甲磺隆(metsulphurone-methyl)，或任何其他揭示在《The Pesticide Manual》,15th edition(2009)或16th edition(2012),C.D.S.Tomlin,British Crop Protection Council中的磺醯基尿素和/或一種或多於一種三唑嘧啶除草劑(例如雙氟磺草胺[florasulam]、甲氧磺草胺[pyroxsulam]或平速爛[penoxsulam])
和/或一種或多於一種嘧啶基(硫代或氧基)苯甲酸鹽除草劑(例如雙草醚[bispyribac-sodium]或環酯草醚[pyriftalid])和/或一種或多於一種磺醯基胺基羰基三唑啉酮除草劑(例如噻吩基卡巴腙-甲基、丙氧基卡巴腙-鈉或氟酮磺隆)和/或咪唑啉酮除草劑(例如甲氧咪草煙[imazamox])。
此種能對抗ACCase和/或ALS抑制劑和/或的嘉磷塞特定實例尤其是大穗看麥娘(Alopecurus myosuroides)、Apera spica-venti、野燕麥(Avena fatua)、Avena sterilis、Brachiaria decumbens、信號草(Brachiaria plantaginea)、大馬唐草(Digitatia horizontalis)、(Digitaria insularis)、血紅色馬唐(Digitaria sanguinalis)、光頭稗(Echinochloa colona)、稗(Echinochloa crus-galli))、牛筋草(Eleusine indica)、(多花黑麥草(Lolium multiflorum)、硬直黑麥草(Lolium rigidum)、黑麥草(Lolium perenne)、小籽虉草(Phalaris minor)、Phalaris paradoxa、狗尾草(Setaria viridis)、大狗尾草(Setaria faberi)或金色狗尾草(Setaria glauca)。
在本發明的一項尤佳之具體實例中，通式(I)之根據本發明的化合物可用於對抗以下有害植株：- 能對抗一種或多於一種ACCase抑制性除草劑(例如選自以上列表)或其實至少部分由於有害植株的ACCase標靶位置中有一個或多於一個胺基酸經突變(例如取代)的植株(請參考例如S.B.Powles and Qin Yu,"Evolution in Action：Plants Resistant to herbicides",Annu.Rev.Plant Biol.,2010,61,p.317-347)；和/或- 能對抗嘉磷塞或其實至少部分由於所提到雜草中的嘉磷塞所導向之EPSPS標靶部位中有一個或多於一個胺基酸經突變(例如取代)的植株；和/或- 能對抗一種或多於一種ALS抑制性除草劑(例如選自以上ALS抑制性除草劑列表)且其實至少部分由於所提到
雜草中的ALS標靶部位中有一個或多於一個胺基酸經突變(例如取代)的植株(請參考例如S.B.Powles and Qin Yu,"Evolution in Action：Plants Resistant to herbicides",Annu.Rev.Plant Biol.,2010,61,p.317-347)；和/或- 能對抗一種或多於一種ACCase抑制性除草劑(例如選自以上列表)和/或嘉磷塞和/或一種或多於一種ALS抑制性除草劑(例如選自以上列表)且其實至少部分經由代謝誘發，例如至少部分因為細胞色素P450-調節之代謝作所用導致除草劑抗性的植株(請參考例如S.B.Powles and Qin Yu,"Evolution in Action：Plants Resistant to herbicides",Annu.Rev.Plant Biol.,2010,61,p.317-347)。
根據本發明的化合物與先前技藝的化合物(例如WO 2015/040114，化合物42.03)相比展現傑出的性質(亦請參考表9和10中的比較數據)。
本發明的化合物可以傳統調配物中的可濕潤粉末、可乳化濃縮物、可噴灑溶液、塵佈用產品或顆粒施用。因此本發明也提供包含本發明化合物的除草和植物生長調節組成物。
根據本發明的化合物可以各種方式調配，此係根據預先給定的生物和/或化學物理的參數。可能的調配物包括，例如：可濕潤的粉末(WP)、水可溶粉末(SP)、水可溶濃縮物、可乳化濃縮物(EC)、乳化物(EW)，如油在水中和水在由中的乳化物、可噴灑溶液、懸浮液濃縮物(SC)、已油禍水為基底的分散物、油可溶混的溶液、膠囊懸浮物(CS)、塵佈用產品(DP)、施用物料、用於散播和土壤施用的顆粒、微顆粒形式的顆粒(GR)、噴灑用顆粒、吸收和吸附用顆粒、水可分散的顆粒(WG)、水可溶顆粒(SG)、ULV調配物、微膠囊和蠟。這些個別的調配物型式基本上是已知的且被說明在例如：Winnacker Küchler,"Chemische Technologie[Chemical Technology]”,Volume 7,C.Hanser Verlag Munich,4th Ed.
1986,Wade van Valkenburg,"Pesticide formulations",Marcel Dekker,N.Y.,1973,K.Martens,"Spray Drying"Handbook,3rd Ed.1979,G.Goodwin Ltd.London。
所需的調配物輔助劑如惰性物質、表面活性劑、溶劑和更多添加物，同樣為已知的並且說明在例如：Watkins,"Handbook of Insecticide Dust Diluents and Carriers",2nd ed.,Darland Books,Caldwell N.J.；H.v.Olphen,"Introduction to Clay Colloid Chemistry",2nd ed.,J.Wiley & Sons,N.Y.；C.Marsden,"Solvents Guide",2nd ed.,Interscience,N.Y.1963；McCutcheon's "Detergents and Emulsifiers Annual",MC Publ.Corp.,Ridgewood N.J.,Sisley and Wood,"Encyclopedia of Surface Active Agents",Chem.Publ.Co.Inc.,N.Y.1964,Schönfeldt,"Grenzflächenaktive Äthylenoxidaddukte [Interface-active ethylene oxide adducts]",Wiss.Verlagsgesell.,Stuttgart 1976,Winnacker Küchler,"Chemische Technologie[Chemical Technology]",Volume 7,C.Hanser Verlag Munich,4th Ed.1986。
在這些調配物的基礎上，亦可與其他具除害劑活性的物質，例如殺昆蟲劑、殺螨劑、除草劑、殺真菌劑，還有與藥害減輕劑、肥料和/或生長調節劑一起生產組合物，例如呈已混合完畢的調配物形式或呈分開以供混桶的形式。適當的藥害減輕劑是例如吡唑解草酯、環丙磺醯胺、雙苯惡唑酸、解毒喹(cloquintocet-mexyl)和二氯丙烯胺(dichlormid)。
可濕潤的粉末是能均勻分散在水中的製備物，其除稀釋劑或惰性物質外與活性成分併存，還包含離子的和/或非離子型式的表面活性劑(濕潤劑，分散劑)，例如聚氧乙基化的烷基分類、聚氧乙基化的脂肪醇類、聚氧乙基化的脂肪胺類、脂肪醇聚乙二醇醚硫酸酯類、烷基磺酸酯類、烷基苯磺酸酯類、木質素磺酸鈉、2,2'-二萘基甲烷-6,6'-二磺酸鈉、二丁基
萘磺酸鈉或其他油醯基甲基牛磺酸鈉。為了生產可濕潤的粉末，吾人將具除草劑活性的成分精細研磨，例如在傳統的裝置如錘磨機、風箱研磨機和氣壓噴射碾磨機，且同時或緊接著與調配物的輔助劑混合。
可乳化的濃縮物系將活性成分溶解在一種有機溶劑中，例如丁醇、環己酮、二甲基甲醯胺、二甲苯、或其他較為高沸點的芳香類或烴類或有機溶劑的混合物，並添加一種或多於一種離子的和/或非離子的表面活性劑(乳化劑)所產生的。可使用的乳化劑實例為：烷芳基磺酸鈣如十二醯基苯磺酸鈣或非離子的乳化劑如脂肪酸聚乙二醇酯類、烷基芳基聚乙二醇醚、脂肪醇聚乙二醇醚、環氧丙烷環氧乙烷縮合產物、烷基聚醚類、山梨糖酯類例如山梨糖脂肪酸酯或聚氧乙烯山梨糖酯例如聚氧乙烯山梨糖脂肪酸酯。
可用於塵佈的粉末係將活性成分與精細分散的固態物質，例如滑石、天然黏土如高嶺土、皂土和葉蠟石，或矽藻土一起研磨而獲得。
懸浮液的濃縮物可用水或油為基底。其可藉由濕磨來生產，利用標準的市售研磨機研磨並且視需要添加表面活性劑，如以上已被列出用於其他型式之調配物者。
乳化物例如油在水中的乳化物(EW)可以例如利用攪拌機、膠體研磨機和/或靜態混合器，使用水溶液的有機溶劑且視需要使用如以上已被列出用於其他型式之調配物的表面活性劑來製備。
顆粒可以藉著將活性成分噴灑到吸附性的顆粒惰性物質上或將活性成分濃縮物利用吸附劑例如聚乙烯醇、聚丙烯酸鈉或其他礦物油施加到載劑如砂子、高嶺土或顆粒的惰性物質表面來製備。適當的活性成分亦可用傳統生產肥料顆粒的方法-若需要在一種與肥料的混合物中予以結粒。
水可分散的顆粒通常是藉由傳統方法如噴灑-乾燥法、流
體化床結粒法、盤皿結粒法、用高速混合機混合並且不加固態惰性物質即予以擠壓成形的方式生產。
盤皿、流體化床、擠壓成形和噴灑顆粒的生產請參考例如，《Spray Drying Handbook》3rd Ed.1979,G.Goodwin Ltd.,London,J.E.Browning,《Agglomeration》,Chemical and Engineering 1967,pages 147 ff,《Perry's Chemical Engineer's Handbook》,5th Ed.,McGraw Hill,New York 1973,p.857中的方法。
更多關於作物保護組成物之調配的細節請參考例如：G.C.Klingman,《Weed Control as a Science》,John Wiley and Sons,Inc.,New York,1961,pages 81-96和J.D.Freyer,S.A.Evans,《Weed Control Handbook》,5th Ed.,Blackwell Scientific Publications,Oxford,1968,pages 101-103。
該農化製備物通常包含0.1到99%重量比，尤其是0.1至95%重量比之根據本發明的化合物。
在可濕潤的粉末中，活性成分的濃度是例如大約10至90%重量比，剩下用來達到100%重量比的物質包括傳統調配物的成分。在可乳化濃縮物的情形中，該活性成分的濃度可為大約1至90，較佳是5至80%重量比。塵粉型式的調配物包含
1至30%重量比的活性成分，較佳是最多5至20%重量比的活性成分，可噴灑溶液包含大約0.05至80，較佳是2至50%重量比的活性成分。在水可分散顆粒的情形中，活性成分含量部分視活性化合物是以液體或固體形式存在以及使用哪種結粒輔助劑、填充劑等。在水可分散的顆粒中，活性成分的含量是介於例如1和95%重量比之間，較佳是介在10和80%重量比之間。
此外，該特定的活性成分調配物視需要包含黏著劑、乳化劑、穿透劑、保存劑、抗凍劑和溶劑、填充劑、運輸劑和
染料、消泡劑、蒸發抑制劑和慣用於每一種情形之影響pH和黏度的用劑。
以這些調配物為基礎，亦可生產與其他具有除害劑活性的物質，例如殺昆蟲劑、殺螨劑、除草劑、殺真菌劑，還有安全劑、肥料和/或生長調節劑生產組合物，例如呈已混合完畢的調配物形式或呈分開以供混桶的形式。
為了施用，呈市售形式調配物若適當，例如在可濕潤粉末、可乳化濃縮物、分散物和水可分散顆粒與水的情形中係以傳統方式稀釋。塵粉型式的製備物、土壤施用的顆粒或用於散播的顆粒和可噴灑溶液則並未在施用前再與其他惰性物質進行慣常的稀釋。
式(I)化合物的所需施用比例因外在條件而異，包括溫度、濕度和所使用的殺草劑型式。其可在寬廣的限制中，例如在0.001和1.0kg/ha之間或更多的活性物質中作改變，但較佳是在0.005和750g/ha之間作改變。
以下實例係藉由舉例說明本發明：
將1.14g(2.67mmol)前驅體溶於10ml DMF的溶液在室溫下經30min滴加到8ml DMF和748mg(2.5eq)三級丁酸鉀，並在此溫度下攪拌18h。然後將混合物在40℃加熱4h，將溶劑減壓移除並將殘留物溶於100ml水中。將混合物用1N鹽酸調整到pH=1並將所得到的殘留物濾出，產生1.00g(95%)目標化合物A1，呈無色油液。
1H-NMR(400MHz,d6-DMSO)：3.33(s,1H,CH2-OCH3),2.04(s,3H,CH3-C≡C)
以相似於實例I-1的方式並且根據與生產有關的一般細節，得到以下根據本發明的化合物：
將0.5ml三乙胺和1.5mg DMAP溶於8ml二氯甲烷添加到根據本發明的化合物(I-11)1.00g(2.6mmol)並且在40℃下攪拌10min。然後緩緩滴加氯甲酸乙酯0.315g(2.9mmol)溶於二氯甲烷2ml的溶液並將混合物在40℃攪拌6小時，然後在RT下至隔夜。添加碳酸氫鈉溶液10ml然後將有機層分出。將濃縮後留下的殘留物用管柱層析術純化(矽膠，梯度EtOAc/正庚烷)，產生0.920g(77%)化合物B1，此係根據乙酸酯/己烷v/v=20：80)，共得到0.43g(47%)反式異構物呈無色晶體，m.p.183-184℃。
以相似於實例Ia-1的方式並且根據與生產有關的一般細節，得到以下式(I-1-b)的化合物：
將1.10g(4.5mmol)4-環丙基乙炔基-2-乙基-6-甲基苯基乙酸溶解在20ml二氯甲烷中並且與一滴DMF混合。添加0.75g(1.3eq)草醯氯並將混合物加熱迴流至沸騰直到氣體停止冒出。然後，將反應溶液濃縮，在每一情形中與20ml二氯甲烷混合兩次以上並且再次濃縮，以便最終將殘留物溶於4ml二氯甲烷(溶液1)中。將1.015(4.5mmol)3-甲氧基甲基環戊烷胺基酸甲酯鹽酸鹽和1g三乙胺溶解在20ml二氯甲烷中並滴加溶液1經90min的時間。攪拌18h之後，將混合物與50ml水混合，把有機相分出，予以濃縮並且用管柱層析術純化(矽膠梯度EtOAc/正庚烷)。這樣產生1.16g
(62%)所需的標靶化合物。
相似於實例II-1且根據生產相關的細節，得到以下式(II)的化合物：
最初將8.41g(32.7mmol)文獻已知的4-溴-2,6二甲基苯基乙酸甲酯添加0.1mol%二氯雙三苯基鈀氯化物溶於45ml三乙胺和18ml吡啶的混合物並且添加4.11g(1.9eq)環丙基乙炔。將混合物加熱迴流至沸騰經7.5h然後在室溫下攪拌至隔夜。將所得到的鹽過濾出來並且在每一情形中用三乙胺和二乙醚沖洗兩次。將母液減壓濃縮，先與水混合然後與32ml之濃度3%的鹽酸溶液混合。然後，用乙酸乙酯進行萃取並將此有機相用水沖洗兩次。使有機相乾燥之後，進行濃縮並且將所得到的殘留物用管柱層析法純化(矽膠，正庚烷/乙酸乙酯)。這樣產生出6.83g(86%)所需化合物。
1H-NMR(400MHz,CDCl3)：7.07(s,2H,Ar-H),3.67(s,5H,OCH3 and CH2-Ar),2.26(s,3H,Ar-CH3),1.42(s,1H,CH-c-Pr)
將7.5g(24.8mmol)2,6-二乙基-4-三甲基矽丙炔基苯基乙酸甲酯溶解在200ml乙醇中並且與4當量氫氧化鉀溶於
200ml乙醇的溶液混合。將混合物迴流加熱至沸騰經7h，把溶液移除並添加500ml水。然後用鹽酸建立其pH值為1並在每一情中將混合物用100ml乙酸乙酯萃取三次。將合併的有機項用硫酸鈉乾燥、濃縮並且用管柱層析術純化(矽膠，EtOAc/正庚烷梯度)。由此產生4.3g根據本發明的化合物(VII-2)。
1H-NMR(400MHz,CDCl3)：7.09和7.07每一者(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,CH 3 -CH2-Ar)
以下化合物係以相似的方式獲得
經挑選實例的1H NMR數據係以1H NMR尖峰列表的形式陳述。對於每一信號尖峰而言，在圓形括弧中首先是以ppm為單位表示的δ值然後是信號的強度被列出。不同信號尖峰之成對的δ值-信號強度數字係以分號彼此分開列示。
因此一項實例的尖峰列表具有以下形式：
δ1(強度1)；δ2(強度2)；........；δi(強度i)；......；δn(強度n)
銳利的信號之強度與印出之NMR光譜實例中以cm為單位的信號高度相關聯並且顯示真正的信號強度比率。在寬扁信號的情形中，數個尖峰或該間的中間及其相對強度可能被顯示出來與該光譜中最強的信號做比較。
為了校正1H-NMR光譜的化學偏移，吾人使用四甲基矽和/或尤其是在DMSO中測量光譜的情形下之溶劑的化學偏移。因此，四甲基矽尖峰並不一定要出現在NMR尖峰列表中。
1H NMR的尖峰列表相似於傳統的1H-NMR印出光譜，因此通常包含所有列在傳統NMR解讀內容中的尖峰。
此外，就像傳統的1H NMR印出光譜，其可顯示溶劑信號、同樣構成本發明之主題要件之部分的目標化合物之立體異構物信號，以及/或是雜質的尖峰。
在吾人的1H NMR尖峰列表中陳述溶劑和或水的δ範圍中之化合物信號時，常見的溶劑尖峰，例如DMSO-D6中的DMSO尖峰和水的尖峰都被顯示出來，通常具有平均說來之高強度。
目標化合物之立體異構物尖峰和/或雜質尖峰通常具有平均而言比目標化合物的尖峰(例如純度>90%)較低的強度。
此種立體異構物和/或雜質對於特別的製備法而言是典型的。因而在此情形中其尖峰可以參考「副產物指紋」以幫助鑑認吾人之製備法的複現性。
藉由已知方法(MestreC、ACD模擬，但亦使用實驗評估出來的期望值)計算目標化合物尖峰的專家若需要可以分離出目標化合物的尖峰，是需要利用另外的強度濾器來進行。此種分離法相似於在傳統的1H-NMR解讀內容中之挑選相
關尖峰。
更多1H NMR尖峰列表的細節見於Research Disclosure Database第564025號。
a)一種塵佈(dusting)產品是藉著將10份重量的式(I)化合物和/或其鹽及90份重量的滑石作為惰性物質相混合並將混合物在一個衝擊式粉碎機中研成粉末來獲得。
b)一種易被水分散之可濕潤粉末係藉著將25份重量的式(I)化合物和/或其鹽、64份重量之含高嶺土的實應作為惰性物質、10份重量的木質素磺酸鉀和一份重量的油醯基甲基牛磺酸鈉作為濕潤劑以及分散劑混合並且在一個多方榫的碟盤粉碎機中研磨而獲得。
c)一種易被水分散之分散物的濃縮液係藉著將20份重量的醚
(®Triton X 207)，3份重量的的異十三醇聚二醇醚(8 EO)和71份重量的石蠟系礦物油(沸點範圍，例如大約255到多於277℃)混合而獲得並將之以球磨式粉碎機研磨至低於5微米的細小程度。
d)一種可乳化的濃縮物係從15份重量的式(I)化合物和/或其鹽、75份重量的環己酮作為溶劑和10份重量的乙氧基化之壬基酚作為乳化劑獲得。
e)水可分散的顆粒係藉由混合以下成分而獲得：75份重量的式(I)化合物和或其鹽，10份重量的木質素磺酸鈣，5份重量的月桂基硫酸鈉，3份重量的聚乙烯醇和7份重量的高嶺土，將混合物在一個多方榫的碟盤粉碎機中研磨，並且使粉末結成顆粒，此係在流體化床上藉著噴灑方式給水作為使其結粒的液體。
f)水可分散的顆粒亦可藉著均質化和預先研成粉末來獲得：25份重量的式(I)化合物和或其鹽，5份重量的2,2'二萘基甲烷-6,6'二磺酸鈉，2份重量的油醯基甲基牛磺酸鈉，1份重量的聚乙烯醇，17份重量的碳酸鈣和50份重量的水在膠體研磨機上，,然後將混合物在一個珠磨機中研磨並在噴灑塔中利用單相噴嘴將所得到的懸浮液霧化且予乾燥。
使單子葉和雙子葉雜草植株和作物植株的種子佈設在木頭纖維盆的砂質土壤中並且用土覆蓋。然後把調配成可濕潤粉末(WP)或乳化物濃縮液(EC)形式之根據本發明的化合物以水溶液的懸浮物或乳化物施用，其水施用比例為600到800l/ha(經換算的)，並添加0.2%濕潤劑到覆蓋土的表面。
處理之後，將盆子放在溫室中並且將其保持在對試驗植株良好的生長條件下。試驗植株的損害是在三週的試驗期後用目測法與未處理的對照組比較來評分(除草劑活性百分率(%)：100%活性=植株已經死亡，0%活性=如同對照組的植株)。
如表5和6所顯示的結果，根據本發明的化合物具有對抗寬廣譜系之雜草和野草的良好除草劑萌芽前處理效果。例如，在每一情形中化合物編號No.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且以320g/ha的施用比例展現80-100%對抗大穗看麥娘(Alopecurus myosuroides)、野燕麥(Avena fatua)、稗(Echinochloa crus-galli)、多花黑麥草(Lolium multiflorum)和狗尾草(Setaria viridis)的效果。相對地，化合物I-7、I-8、I-13、Ia-4和Ia-16，在每一情形中以320g/ha的施用比例展現80-100%對抗大穗看麥娘(Alopecurus myosuroides)、稗(Echinochloa crus-galli)、多花黑麥草(Lolium multiflorum)和狗尾草(Setaria viridis)的效果。因此，根據本發明的化合物適用於藉由萌芽前處理法防治不想要的植株生長。
單子葉和雙子葉雜草和作物植株的種子被攤放木頭纖維盆裡的砂質土壤中，用土壤覆蓋並且在良好的生長條件下的溫室中培養。播種2到3週後，在單片葉子階段對試驗植行處理。根據本發明的化合物，經調配成可濕潤粉末(WP)的形式調配或呈乳化濃縮物(EC)，然後以水溶液的懸浮物或乳化物，以600到800l/ha(經轉換的)的水施用比例並添加0.2%的濕潤劑噴灑在植株的綠色部分。該試驗植株已被放置在溫室中在最佳生長條件下經大約三週之後，與未經處理的對照組比較以目測評估該製備物的作用(除草劑作用百分率(%)：100%活性=植株已死，0%活性=看起來像對照組植株)。
如表7和表8的結果所顯示的，根據本發明的化合物具有對抗寬廣譜系之雜草和野草的良好除草劑萌芽後處理效果。例如，化合物編號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且以80g/ha的施用比例展現80-100%對抗大穗看麥娘(Alopecurus myosuroides)、野燕麥(Avena fatua)、稗(Echinochloa crus-galli)、多花黑麥草(Lolium multiflorum)和
狗尾草(Setaria viridis)的效果。因此，根據本發明的化合物適用於藉由萌芽後處理法防治不想要的植株生長。
與最近的技藝(WO 2015/040114，化合物42.03)相比較，本發明的化合物對於萌芽前處理和萌芽後除理均具有改良的除草劑效果，如下表所顯示的。
Claims (24)
- 式(I)之經炔基取代之N-苯基吡咯啶-2,4-二酮
- 根據請求項1之通式(I)的化合物或其農化上可接受的鹽，其中X和Y彼此獨立在每一情形中為C1-C4-烷基或C3-C6-烷基。
- 根據請求項2之通式(I)的化合物或其農化上可接受的鹽，其中X和Y彼此獨立在每一情形中定義為甲基、乙基或環丙基。
- 根據請求項1或2之通式(I)的化合物或其農化上可接受的鹽，其中R1=甲基、乙基、異丙基或環丙基.
- 根據請求項1或2之通式(I)的化合物或其農化上可接受的鹽，其中n和m在每一情形中彼此獨立定義為1或2。
- 根據請求項1或2之通式(I)的化合物或其農化上可接受的鹽，其中R3=C1-C3-烷氧基-C1-C3-烷基。
- 根據請求項1或2之通式(I)的化合物或其農化上可接受的鹽，其中G=氫，或選自以下之可切斷的基團L：
- 根據請求項7之通式(I)的化合物，其中G=氫、或選自以下之可切割L基團，
- 根據請求項1之通式(I)的化合物或其農化上可接受的鹽，其中X=甲基、乙基或環丙基，Y=甲基或乙基，R1=甲基、乙基、異丙基或環丙基，且R3=CH3CH2OCH2-或CH3OCH2。
- 根據請求項1至8之通式(I)的化合物或其農化上可接受的鹽，其中X=甲基且Y=乙基。
- 根據請求項1之通式(I)的化合物或其農化上可接受的鹽，其中X=甲基、乙基或環丙基，Y=甲基、乙基，R1=甲基、乙基、異丙基或環丙基，且R2=氫，R3=CH3CH2OCH2-或CH3OCH2n和m在每一情形中彼此獨立為1或2，G=氫，或一個選自以下的可切斷之基團L
- 一種通式(VII)之經炔基取代之苯基乙酸，
- 根據請求項13之通式(VII)的化合物，其中X=甲基、乙基或環丙基；Y=甲基或乙基，且R1=甲基、乙基、異丙基或環丙基，其中化合物2、6-二甲基-4-炔丙基苯基乙酸除外。
- 一種除草劑組成物，其包含根據請求項1至11中任一項之通式(I)的化合物或其農藥上可接受的鹽且視需要一種農藥上可接受的載劑、稀釋劑和/或溶劑。
- 根據請求項14之除草劑組成物，其包含至少另一種出自殺昆蟲劑、殺螨劑、除草劑、殺真菌劑、安全劑和生長調節劑之群組的除害劑活性成分。
- 根據請求項15之除草劑組成物，其包含一種安全劑。
- 根據請求項14到16之除草劑組成物，其尚包含另一種除草劑。
- 一種防治不想要的植株生長之方法，其中根據請求項1至11中任一項之化合物被施用於待防治的植株、植株部分、植株種子或不想要的植株生長之區域。
- 根據請求項18的方法，其中該不想要的植株生長係挑選自似草的單子葉雜草。
- 根據請求項18或19的方法，其中在有用植株中具有抗藥性的雜草之生長被防治，且其中根據請求項1至11中任一項之除草劑組成物被施用於待防治的雜草。
- 根據請求項20的方法，其中該有用的植株係選自小麥、大麥、裸麥、燕麥、稻米、甘蔗、大豆、油菜、葵花和玉米。
- 防治有害植株的方法，其中使用根據請求項1之式(I)化合物或其農化上可接受的鹽。
- 根據請求項22的方法，特徵在於式(I)化合物或其農化上可接受的鹽被用於防治有用的植株作物中之有害植株。
- 根據請求項23的方法，其特徵在於該有用的植株為基因轉殖的有用植株。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15173092 | 2015-06-22 | ||
| EP15173092.6 | 2015-06-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201718486A true TW201718486A (zh) | 2017-06-01 |
| TWI706933B TWI706933B (zh) | 2020-10-11 |
Family
ID=53476742
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW105119256A TWI706933B (zh) | 2015-06-22 | 2016-06-20 | 新穎之經炔基取代之３-苯基吡咯啶-２,４-二酮及其作為除草劑之用途 |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US10899709B2 (zh) |
| EP (1) | EP3310759B1 (zh) |
| JP (1) | JP6796088B2 (zh) |
| KR (1) | KR20180019209A (zh) |
| CN (2) | CN112159321A (zh) |
| AR (1) | AR105086A1 (zh) |
| AU (2) | AU2016282731B2 (zh) |
| BR (1) | BR112017028008B1 (zh) |
| CA (1) | CA2990078A1 (zh) |
| EA (1) | EA035579B1 (zh) |
| ES (1) | ES2730523T3 (zh) |
| PL (1) | PL3310759T3 (zh) |
| TW (1) | TWI706933B (zh) |
| UA (1) | UA120656C2 (zh) |
| UY (1) | UY36743A (zh) |
| WO (1) | WO2016207097A1 (zh) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9340799B2 (en) | 2013-09-06 | 2016-05-17 | President And Fellows Of Harvard College | MRNA-sensing switchable gRNAs |
| US11178868B2 (en) * | 2015-10-06 | 2021-11-23 | Bayer Cropscience Aktiengesellschaft | Alkynyl-substituted 3-phenylpyrrolidine-2,4-diones and use thereof as herbicides |
| JP7109784B2 (ja) | 2015-10-23 | 2022-08-01 | プレジデント アンド フェローズ オブ ハーバード カレッジ | 遺伝子編集のための進化したＣａｓ９蛋白質 |
| KR102547316B1 (ko) | 2016-08-03 | 2023-06-23 | 프레지던트 앤드 펠로우즈 오브 하바드 칼리지 | 아데노신 핵염기 편집제 및 그의 용도 |
| US11542509B2 (en) | 2016-08-24 | 2023-01-03 | President And Fellows Of Harvard College | Incorporation of unnatural amino acids into proteins using base editing |
| WO2018119359A1 (en) | 2016-12-23 | 2018-06-28 | President And Fellows Of Harvard College | Editing of ccr5 receptor gene to protect against hiv infection |
| JP2020510038A (ja) | 2017-03-09 | 2020-04-02 | プレジデント アンド フェローズ オブ ハーバード カレッジ | がんワクチン |
| EP3592853A1 (en) | 2017-03-09 | 2020-01-15 | President and Fellows of Harvard College | Suppression of pain by gene editing |
| JP2020510439A (ja) | 2017-03-10 | 2020-04-09 | プレジデント アンド フェローズ オブ ハーバード カレッジ | シトシンからグアニンへの塩基編集因子 |
| WO2019023680A1 (en) | 2017-07-28 | 2019-01-31 | President And Fellows Of Harvard College | METHODS AND COMPOSITIONS FOR EVOLUTION OF BASIC EDITORS USING PHAGE-ASSISTED CONTINUOUS EVOLUTION (PACE) |
| US10743535B2 (en) | 2017-08-18 | 2020-08-18 | H&K Solutions Llc | Insecticide for flight-capable pests |
| EP3676376B1 (en) | 2017-08-30 | 2025-01-15 | President and Fellows of Harvard College | High efficiency base editors comprising gam |
| WO2019118949A1 (en) | 2017-12-15 | 2019-06-20 | The Broad Institute, Inc. | Systems and methods for predicting repair outcomes in genetic engineering |
| EP3797160A1 (en) | 2018-05-23 | 2021-03-31 | The Broad Institute Inc. | Base editors and uses thereof |
| US12522807B2 (en) | 2018-07-09 | 2026-01-13 | The Broad Institute, Inc. | RNA programmable epigenetic RNA modifiers and uses thereof |
| WO2020092453A1 (en) | 2018-10-29 | 2020-05-07 | The Broad Institute, Inc. | Nucleobase editors comprising geocas9 and uses thereof |
| US12351837B2 (en) | 2019-01-23 | 2025-07-08 | The Broad Institute, Inc. | Supernegatively charged proteins and uses thereof |
| EA202192467A1 (ru) * | 2019-03-15 | 2022-02-16 | Байер Акциенгезельшафт | Специфически замещенные 3-(2-галоген-6-алкил-4-пропинилфенил)-3-пирролин-2-оны и их применение в качестве гербицидов |
| CA3133184A1 (en) * | 2019-03-15 | 2020-09-24 | Bayer Aktiengesellschaft | Specifically substituted 3-phenyl-5-spirocyclopentyl-3-pyrrolin-2-ones and their use as herbicides |
| JP7657726B2 (ja) | 2019-03-19 | 2025-04-07 | ザ ブロード インスティテュート，インコーポレーテッド | 編集ヌクレオチド配列を編集するための方法および組成物 |
| US12473543B2 (en) | 2019-04-17 | 2025-11-18 | The Broad Institute, Inc. | Adenine base editors with reduced off-target effects |
| US12435330B2 (en) | 2019-10-10 | 2025-10-07 | The Broad Institute, Inc. | Methods and compositions for prime editing RNA |
| DE112021002672T5 (de) | 2020-05-08 | 2023-04-13 | President And Fellows Of Harvard College | Vefahren und zusammensetzungen zum gleichzeitigen editieren beider stränge einer doppelsträngigen nukleotid-zielsequenz |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL62794A0 (en) * | 1980-06-02 | 1981-07-31 | American Cyanamid Co | Substituted nicotinic acid esters and salts thereof and their use as herbicidal agents |
| DE4223015A1 (de) * | 1992-07-13 | 1994-01-20 | Bayer Ag | Substituierte 3-Benzoyl-pyrrolidin-2,4-dion-Derivate |
| AU2623399A (en) * | 1999-02-11 | 2000-08-29 | Novartis Ag | 3-hydroxy-4-aryl-5-pyrazoline derivatives as herbicides |
| RU2269537C2 (ru) * | 1999-09-07 | 2006-02-10 | Зингента Партисипейшнс Аг | Фенилзамещенные гетероциклические 1,3-кетоенолы, способ их получения, гербицидное средство на их основе и способ борьбы с ростом нежелательной растительности |
| DE10016544A1 (de) * | 2000-04-03 | 2001-10-11 | Bayer Ag | C2-phenylsubstituierte Ketoenole |
| DE10239479A1 (de) * | 2002-08-28 | 2004-03-04 | Bayer Cropscience Ag | Substituierte spirocyclische Ketoenole |
| DE10311300A1 (de) * | 2003-03-14 | 2004-09-23 | Bayer Cropscience Ag | 2,4,6-Phenylsubstituierte cyclische Ketoenole |
| DE102005051325A1 (de) * | 2005-10-27 | 2007-05-03 | Bayer Cropscience Ag | Alkoxyalkyl spirocyclische Tetram- und Tetronsäuren |
| DE102005059891A1 (de) * | 2005-12-15 | 2007-06-28 | Bayer Cropscience Ag | 3'-Alkoxy-spirocyclopentyl substituierte Tetram- und Tetronsäuren |
| DE102006018828A1 (de) * | 2006-04-22 | 2007-10-25 | Bayer Cropscience Ag | Alkoxyalkyl-substituierte cyclische Ketoenole |
| EP2020413A1 (de) * | 2007-08-02 | 2009-02-04 | Bayer CropScience AG | Oxaspirocyclische-spiro-substituierte Tetram- und Tetronsäure-Derivate |
| US8846946B2 (en) * | 2008-12-02 | 2014-09-30 | Bayer Cropscience Ag | Germinal alkoxy/alkylspirocyclic substituted tetramate derivatives |
| US8389443B2 (en) | 2008-12-02 | 2013-03-05 | Bayer Cropscience Ag | Geminal alkoxy/alkylspirocyclic substituted tetramate derivatives |
| CN102348684B (zh) * | 2009-03-11 | 2014-11-12 | 拜尔农作物科学股份公司 | 被卤代烷基亚甲基氧基苯基取代的酮烯醇 |
| CN103003239A (zh) * | 2010-05-31 | 2013-03-27 | 先正达参股股份有限公司 | 基于螺杂环吡咯烷衍生物的杀虫剂 |
| KR101789527B1 (ko) * | 2011-03-01 | 2017-10-25 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | 2-아실옥시피롤린-4-온 |
| WO2013079708A1 (en) * | 2011-11-30 | 2013-06-06 | Syngenta Limited | 2-(substituted-phenyl)-cyclopentane-1,3-dione compounds, and derivatives thereof |
| GB201120644D0 (en) * | 2011-11-30 | 2012-01-11 | Syngenta Participations Ag | Herbicidal uses of compounds |
| WO2015032702A1 (en) * | 2013-09-06 | 2015-03-12 | Syngenta Limited | Herbicidally active 2-halogen-4-alkynyl- phenyl-pyrazolidine-dione or pyrrolidine-dione derivatives |
| WO2015040114A1 (en) * | 2013-09-20 | 2015-03-26 | Syngenta Limited | Herbicidally active 2-halogen-4-alkynyl-phenyl-pyrazolidine-dione or pyrrolidine-dione derivatives |
-
2016
- 2016-06-20 UY UY0001036743A patent/UY36743A/es not_active Application Discontinuation
- 2016-06-20 CN CN202011181795.2A patent/CN112159321A/zh active Pending
- 2016-06-20 BR BR112017028008-6A patent/BR112017028008B1/pt not_active IP Right Cessation
- 2016-06-20 CN CN201680047578.XA patent/CN107922333B/zh not_active Expired - Fee Related
- 2016-06-20 AU AU2016282731A patent/AU2016282731B2/en not_active Ceased
- 2016-06-20 UA UAA201800593A patent/UA120656C2/uk unknown
- 2016-06-20 PL PL16730835T patent/PL3310759T3/pl unknown
- 2016-06-20 EA EA201890109A patent/EA035579B1/ru not_active IP Right Cessation
- 2016-06-20 WO PCT/EP2016/064132 patent/WO2016207097A1/de not_active Ceased
- 2016-06-20 CA CA2990078A patent/CA2990078A1/en not_active Abandoned
- 2016-06-20 KR KR1020187001755A patent/KR20180019209A/ko not_active Withdrawn
- 2016-06-20 EP EP16730835.2A patent/EP3310759B1/de not_active Not-in-force
- 2016-06-20 TW TW105119256A patent/TWI706933B/zh not_active IP Right Cessation
- 2016-06-20 JP JP2017566122A patent/JP6796088B2/ja not_active Expired - Fee Related
- 2016-06-20 ES ES16730835T patent/ES2730523T3/es active Active
- 2016-06-20 US US15/738,292 patent/US10899709B2/en not_active Expired - Fee Related
- 2016-06-21 AR ARP160101855A patent/AR105086A1/es active IP Right Grant
-
2020
- 2020-07-17 AU AU2020205345A patent/AU2020205345B2/en not_active Ceased
- 2020-09-30 US US17/039,232 patent/US20210024465A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| UA120656C2 (uk) | 2020-01-10 |
| BR112017028008B1 (pt) | 2022-07-12 |
| BR112017028008A2 (pt) | 2018-08-28 |
| EP3310759B1 (de) | 2019-03-20 |
| EA035579B1 (ru) | 2020-07-09 |
| ES2730523T3 (es) | 2019-11-11 |
| TWI706933B (zh) | 2020-10-11 |
| AU2016282731B2 (en) | 2020-07-02 |
| US20180170872A1 (en) | 2018-06-21 |
| KR20180019209A (ko) | 2018-02-23 |
| EA201890109A1 (ru) | 2018-07-31 |
| CN107922333A (zh) | 2018-04-17 |
| EP3310759A1 (de) | 2018-04-25 |
| US10899709B2 (en) | 2021-01-26 |
| CA2990078A1 (en) | 2016-12-29 |
| AR105086A1 (es) | 2017-09-06 |
| JP2018521045A (ja) | 2018-08-02 |
| US20210024465A1 (en) | 2021-01-28 |
| CN107922333B (zh) | 2021-03-30 |
| JP6796088B2 (ja) | 2020-12-02 |
| AU2020205345B2 (en) | 2021-05-13 |
| UY36743A (es) | 2017-01-31 |
| CN112159321A (zh) | 2021-01-01 |
| AU2016282731A1 (en) | 2018-02-01 |
| AU2020205345A1 (en) | 2020-08-06 |
| PL3310759T3 (pl) | 2019-09-30 |
| WO2016207097A1 (de) | 2016-12-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2020205345B2 (en) | New alkynyl-substituted 3-phenylpyrrolidine-2,4-diones and use thereof as herbicides | |
| AU2016336174B2 (en) | New alkynyl-substituted 3-phenylpyrrolidine-2,4-diones and use thereof as herbicides | |
| AU2017249659A1 (en) | Anellated 3-phenyl tetramic acid derivatives having a herbicidal effect |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |