EA024229B1 - Соединения, регулирующие рост растений - Google Patents
Соединения, регулирующие рост растений Download PDFInfo
- Publication number
- EA024229B1 EA024229B1 EA201400348A EA201400348A EA024229B1 EA 024229 B1 EA024229 B1 EA 024229B1 EA 201400348 A EA201400348 A EA 201400348A EA 201400348 A EA201400348 A EA 201400348A EA 024229 B1 EA024229 B1 EA 024229B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- alkyl
- hydrogen
- methyl
- oxygen
- amino
- Prior art date
Links
- 230000001105 regulatory effect Effects 0.000 title claims abstract description 13
- 230000012010 growth Effects 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 134
- 239000000203 mixture Substances 0.000 claims abstract description 85
- 238000000034 method Methods 0.000 claims abstract description 42
- 230000007226 seed germination Effects 0.000 claims abstract description 20
- 230000008635 plant growth Effects 0.000 claims abstract description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 59
- 239000001257 hydrogen Substances 0.000 claims description 53
- -1 C2-S6galogenalkinil Chemical group 0.000 claims description 45
- 241000196324 Embryophyta Species 0.000 claims description 41
- 229910052760 oxygen Inorganic materials 0.000 claims description 40
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 39
- 239000001301 oxygen Chemical group 0.000 claims description 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
- 229910052736 halogen Inorganic materials 0.000 claims description 35
- 150000002367 halogens Chemical class 0.000 claims description 34
- 150000002431 hydrogen Chemical class 0.000 claims description 34
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 150000001412 amines Chemical class 0.000 claims description 17
- 239000011593 sulfur Chemical group 0.000 claims description 17
- 229910052717 sulfur Chemical group 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 12
- 230000035784 germination Effects 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 10
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 10
- 238000009472 formulation Methods 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 8
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 230000004936 stimulating effect Effects 0.000 claims description 6
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 5
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 5
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 5
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 5
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- 239000004009 herbicide Substances 0.000 claims description 5
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 150000003973 alkyl amines Chemical class 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 230000001276 controlling effect Effects 0.000 claims description 3
- 230000002363 herbicidal effect Effects 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- ZNPKAOCQMDJBIK-UHFFFAOYSA-N nitrocyanamide Chemical group [O-][N+](=O)NC#N ZNPKAOCQMDJBIK-UHFFFAOYSA-N 0.000 claims description 3
- 239000005648 plant growth regulator Substances 0.000 claims description 3
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 3
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical group [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 2
- 125000000232 haloalkynyl group Chemical group 0.000 claims 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 150000001647 brassinosteroids Chemical class 0.000 abstract description 5
- 238000002360 preparation method Methods 0.000 abstract description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 105
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
- 239000000243 solution Substances 0.000 description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 26
- 239000002904 solvent Substances 0.000 description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
- 235000019341 magnesium sulphate Nutrition 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- 238000003818 flash chromatography Methods 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
- 229910052796 boron Inorganic materials 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
- 238000004807 desolvation Methods 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 235000019253 formic acid Nutrition 0.000 description 10
- 239000007789 gas Substances 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 240000008042 Zea mays Species 0.000 description 9
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 8
- 235000009973 maize Nutrition 0.000 description 8
- 239000004530 micro-emulsion Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 239000008187 granular material Substances 0.000 description 7
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
- 238000009331 sowing Methods 0.000 description 6
- 239000000080 wetting agent Substances 0.000 description 6
- ANSWUDIVIZMMJJ-UHFFFAOYSA-N 4-[(5-cyanopyridin-2-yl)amino]-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)NC1=CC=C(C#N)C=N1 ANSWUDIVIZMMJJ-UHFFFAOYSA-N 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 5
- 244000299507 Gossypium hirsutum Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 241000209140 Triticum Species 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 239000004495 emulsifiable concentrate Substances 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 4
- 244000046052 Phaseolus vulgaris Species 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 238000005917 acylation reaction Methods 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- FEEPYVFCBPMCNC-UHFFFAOYSA-N benzyl 4-oxo-4-[[5-(trifluoromethyl)pyridin-2-yl]amino]butanoate Chemical compound N1=CC(C(F)(F)F)=CC=C1NC(=O)CCC(=O)OCC1=CC=CC=C1 FEEPYVFCBPMCNC-UHFFFAOYSA-N 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 229910052793 cadmium Inorganic materials 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 238000010353 genetic engineering Methods 0.000 description 4
- ZBJZOLDFULCICJ-UHFFFAOYSA-N methyl 4-[(5-bromopyridin-2-yl)amino]-4-oxobutanoate Chemical compound COC(=O)CCC(=O)NC1=CC=C(Br)C=N1 ZBJZOLDFULCICJ-UHFFFAOYSA-N 0.000 description 4
- XVLWZYCSHYTTND-UHFFFAOYSA-N methyl 4-[(5-ethenylpyridin-2-yl)amino]-4-oxobutanoate Chemical compound COC(=O)CCC(=O)NC1=CC=C(C=C)C=N1 XVLWZYCSHYTTND-UHFFFAOYSA-N 0.000 description 4
- LNDJROFUNYXFHT-UHFFFAOYSA-N methyl 4-oxo-4-[(5-pyridin-3-ylpyridin-2-yl)amino]butanoate Chemical compound C1=NC(NC(=O)CCC(=O)OC)=CC=C1C1=CC=CN=C1 LNDJROFUNYXFHT-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 239000003053 toxin Substances 0.000 description 4
- 231100000765 toxin Toxicity 0.000 description 4
- 108700012359 toxins Proteins 0.000 description 4
- 230000009261 transgenic effect Effects 0.000 description 4
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- OUKGQNHLBZECRP-UHFFFAOYSA-N 4-oxo-4-[[5-(trifluoromethyl)pyridin-2-yl]amino]butanoic acid Chemical compound OC(=O)CCC(=O)NC1=CC=C(C(F)(F)F)C=N1 OUKGQNHLBZECRP-UHFFFAOYSA-N 0.000 description 3
- KDVBYUUGYXUXNL-UHFFFAOYSA-N 6-aminopyridine-3-carbonitrile Chemical compound NC1=CC=C(C#N)C=N1 KDVBYUUGYXUXNL-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 206010065042 Immune reconstitution inflammatory syndrome Diseases 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000002595 Solanum tuberosum Nutrition 0.000 description 3
- 244000061456 Solanum tuberosum Species 0.000 description 3
- 239000002253 acid Chemical class 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 3
- 238000009395 breeding Methods 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- YQXBDYCSGSWPGD-UHFFFAOYSA-N butyl 4-[(5-cyanopyridin-2-yl)amino]-4-oxobutanoate Chemical compound CCCCOC(=O)CCC(=O)NC1=CC=C(C#N)C=N1 YQXBDYCSGSWPGD-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
- 238000013270 controlled release Methods 0.000 description 3
- 239000013256 coordination polymer Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- PIBTXZLZMGJYQQ-UHFFFAOYSA-N methyl 4-[(5-cyanopyridin-2-yl)amino]-4-oxobutanoate Chemical compound COC(=O)CCC(=O)NC1=CC=C(C#N)C=N1 PIBTXZLZMGJYQQ-UHFFFAOYSA-N 0.000 description 3
- QIFQDWUTNJMCKF-UHFFFAOYSA-N methyl 4-[(5-ethynylpyridin-2-yl)amino]-4-oxobutanoate Chemical compound COC(=O)CCC(=O)NC1=CC=C(C#C)C=N1 QIFQDWUTNJMCKF-UHFFFAOYSA-N 0.000 description 3
- FAJTWHJKDFDPJN-UHFFFAOYSA-N methyl 4-[[5-(5-methyl-1,2,4-oxadiazol-3-yl)pyridin-2-yl]amino]-4-oxobutanoate Chemical compound C1=NC(NC(=O)CCC(=O)OC)=CC=C1C1=NOC(C)=N1 FAJTWHJKDFDPJN-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012011 nucleophilic catalyst Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 230000001737 promoting effect Effects 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 3
- 239000000375 suspending agent Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- JLIDBLDQVAYHNE-YKALOCIXSA-N (+)-Abscisic acid Chemical compound OC(=O)/C=C(/C)\C=C\[C@@]1(O)C(C)=CC(=O)CC1(C)C JLIDBLDQVAYHNE-YKALOCIXSA-N 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
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- SYELZBGXAIXKHU-UHFFFAOYSA-N dodecyldimethylamine N-oxide Chemical compound CCCCCCCCCCCC[N+](C)(C)[O-] SYELZBGXAIXKHU-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- MBJHNKNRLKLUIS-UHFFFAOYSA-N ethyl 4-[(5-cyanopyridin-2-yl)amino]-4-oxobutanoate Chemical compound CCOC(=O)CCC(=O)NC1=CC=C(C#N)C=N1 MBJHNKNRLKLUIS-UHFFFAOYSA-N 0.000 description 1
- SIBXWVBJYVGWMJ-UHFFFAOYSA-N ethyl 4-chloro-4-oxobutanoate methyl 4-chloro-4-oxobutanoate Chemical class ClC(=O)CCC(=O)OCC.ClC(=O)CCC(=O)OC SIBXWVBJYVGWMJ-UHFFFAOYSA-N 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000003448 gibberellin Substances 0.000 description 1
- IXORZMNAPKEEDV-OBDJNFEBSA-N gibberellin A3 Chemical class C([C@@]1(O)C(=C)C[C@@]2(C1)[C@H]1C(O)=O)C[C@H]2[C@]2(C=C[C@@H]3O)[C@H]1[C@]3(C)C(=O)O2 IXORZMNAPKEEDV-OBDJNFEBSA-N 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 125000004995 haloalkylthio group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- JYVHOGDBFNJNMR-UHFFFAOYSA-N hexane;hydrate Chemical compound O.CCCCCC JYVHOGDBFNJNMR-UHFFFAOYSA-N 0.000 description 1
- 239000003688 hormone derivative Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 description 1
- 229940056881 imidacloprid Drugs 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 230000000155 isotopic effect Effects 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 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 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 235000021374 legumes Nutrition 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical class [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 235000011160 magnesium carbonates Nutrition 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052752 metalloid Inorganic materials 0.000 description 1
- 150000002738 metalloids Chemical class 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- JERCUTAUWPSTEY-UHFFFAOYSA-N methyl 4-[(3,5-dichloropyridin-2-yl)amino]-4-oxobutanoate Chemical compound COC(=O)CCC(=O)NC1=NC=C(Cl)C=C1Cl JERCUTAUWPSTEY-UHFFFAOYSA-N 0.000 description 1
- DXMFZXILUJMZBB-UHFFFAOYSA-N methyl 4-[(3-bromo-5-chloropyridin-2-yl)amino]-4-oxobutanoate Chemical compound COC(=O)CCC(=O)Nc1ncc(Cl)cc1Br DXMFZXILUJMZBB-UHFFFAOYSA-N 0.000 description 1
- FDPAMMZGFJSOPN-UHFFFAOYSA-N methyl 4-[(5-bromo-3-chloropyridin-2-yl)amino]-4-oxobutanoate Chemical compound COC(=O)CCC(=O)Nc1ncc(Br)cc1Cl FDPAMMZGFJSOPN-UHFFFAOYSA-N 0.000 description 1
- LUHWLMHCEGZIND-UHFFFAOYSA-N methyl 4-[(5-bromo-4-methoxypyridin-2-yl)amino]-4-oxobutanoate Chemical compound COC(=O)CCC(=O)NC1=CC(OC)=C(Br)C=N1 LUHWLMHCEGZIND-UHFFFAOYSA-N 0.000 description 1
- QLPDWPHVUYPACB-UHFFFAOYSA-N methyl 4-[(5-bromo-6-chloropyridin-2-yl)amino]-4-oxobutanoate Chemical compound COC(=O)CCC(=O)NC1=CC=C(Br)C(Cl)=N1 QLPDWPHVUYPACB-UHFFFAOYSA-N 0.000 description 1
- SDPSXHFEGIIMAQ-UHFFFAOYSA-N methyl 4-[(5-chloro-4-ethoxypyridin-2-yl)amino]-4-oxobutanoate Chemical compound CCOC1=CC(NC(=O)CCC(=O)OC)=NC=C1Cl SDPSXHFEGIIMAQ-UHFFFAOYSA-N 0.000 description 1
- HSVAYXSRXZXHJZ-UHFFFAOYSA-N methyl 4-[(5-chloro-4-methoxypyridin-2-yl)amino]-4-oxobutanoate Chemical compound COC(=O)CCC(=O)NC1=CC(OC)=C(Cl)C=N1 HSVAYXSRXZXHJZ-UHFFFAOYSA-N 0.000 description 1
- AVTIMOGBXBSMMQ-UHFFFAOYSA-N methyl 4-[(5-chloro-6-methoxypyridin-2-yl)amino]-4-oxobutanoate Chemical compound COC(=O)CCC(=O)NC1=CC=C(Cl)C(OC)=N1 AVTIMOGBXBSMMQ-UHFFFAOYSA-N 0.000 description 1
- IQKXDTYFWWYVRV-UHFFFAOYSA-N methyl 4-[(5-cyano-3-methoxypyridin-2-yl)amino]-4-oxobutanoate Chemical compound COC(=O)CCC(=O)Nc1ncc(cc1OC)C#N IQKXDTYFWWYVRV-UHFFFAOYSA-N 0.000 description 1
- UQSKTWXTRUPJMU-UHFFFAOYSA-N methyl 4-[(5-cyano-3-methylpyridin-2-yl)amino]-4-oxobutanoate Chemical compound COC(=O)CCC(=O)NC1=NC=C(C#N)C=C1C UQSKTWXTRUPJMU-UHFFFAOYSA-N 0.000 description 1
- RLLHKNCMHPEXMK-UHFFFAOYSA-N methyl 4-[(5-cyanopyridin-2-yl)amino]-2,2-dimethyl-4-oxobutanoate Chemical compound COC(=O)C(C)(C)CC(=O)NC1=CC=C(C#N)C=N1 RLLHKNCMHPEXMK-UHFFFAOYSA-N 0.000 description 1
- GNKHHDAULJWJHL-UHFFFAOYSA-N methyl 4-[(5-methylsulfanylpyridin-2-yl)amino]-4-oxobutanoate Chemical compound COC(=O)CCC(=O)Nc1ccc(SC)cn1 GNKHHDAULJWJHL-UHFFFAOYSA-N 0.000 description 1
- HGWRJVCZCPZGMQ-UHFFFAOYSA-N methyl 4-[(5-methylsulfonylpyridin-2-yl)amino]-4-oxobutanoate Chemical compound COC(=O)CCC(=O)NC1=CC=C(S(C)(=O)=O)C=N1 HGWRJVCZCPZGMQ-UHFFFAOYSA-N 0.000 description 1
- PDBPLKFZGNWKEP-UHFFFAOYSA-N methyl 4-[(5-nitropyridin-2-yl)amino]-4-oxobutanoate Chemical compound COC(=O)CCC(=O)NC1=CC=C([N+]([O-])=O)C=N1 PDBPLKFZGNWKEP-UHFFFAOYSA-N 0.000 description 1
- PYXAGEBOZXCOOT-UHFFFAOYSA-N methyl 4-[[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino]-4-oxobutanoate Chemical compound COC(=O)CCC(=O)NC1=NC=C(C(F)(F)F)C=C1Cl PYXAGEBOZXCOOT-UHFFFAOYSA-N 0.000 description 1
- GPEQHIKADXGDEZ-UHFFFAOYSA-N methyl 4-[[5-bromo-3-(trifluoromethyl)pyridin-2-yl]amino]-4-oxobutanoate Chemical compound COC(=O)CCC(=O)NC1=NC=C(Br)C=C1C(F)(F)F GPEQHIKADXGDEZ-UHFFFAOYSA-N 0.000 description 1
- NXQQISJXUALFFR-UHFFFAOYSA-N methyl 4-[[5-cyano-3-(trifluoromethyl)pyridin-2-yl]amino]-4-oxobutanoate Chemical compound COC(=O)CCC(=O)NC1=NC=C(C#N)C=C1C(F)(F)F NXQQISJXUALFFR-UHFFFAOYSA-N 0.000 description 1
- LKYRJNRMQGQFFT-UHFFFAOYSA-N methyl 4-oxo-4-[[5-(2-trimethylsilylethynyl)pyridin-2-yl]amino]butanoate Chemical compound COC(=O)CCC(=O)NC1=CC=C(C#C[Si](C)(C)C)C=N1 LKYRJNRMQGQFFT-UHFFFAOYSA-N 0.000 description 1
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- QJPQVXSHYBGQGM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QJPQVXSHYBGQGM-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
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- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
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- 239000011148 porous material Substances 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
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- 239000003380 propellant Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 235000015136 pumpkin Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- HZRSNVGNWUDEFX-UHFFFAOYSA-N pyraclostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NN(C=2C=CC(Cl)=CC=2)C=C1 HZRSNVGNWUDEFX-UHFFFAOYSA-N 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
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- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 229940057950 sodium laureth sulfate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- SXHLENDCVBIJFO-UHFFFAOYSA-M sodium;2-[2-(2-dodecoxyethoxy)ethoxy]ethyl sulfate Chemical compound [Na+].CCCCCCCCCCCCOCCOCCOCCOS([O-])(=O)=O SXHLENDCVBIJFO-UHFFFAOYSA-M 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical class [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
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- 238000006467 substitution reaction Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 235000001508 sulfur Nutrition 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
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- 235000012222 talc Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
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- ARYHTUPFQTUBBG-UHFFFAOYSA-N thiophen-2-ylboronic acid Chemical compound OB(O)C1=CC=CS1 ARYHTUPFQTUBBG-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
- CFQJBWKKHCMCGJ-UHFFFAOYSA-N tributyl(pyridin-3-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CN=C1 CFQJBWKKHCMCGJ-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical compound C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- RVKCCVTVZORVGD-UHFFFAOYSA-N trinexapac-ethyl Chemical group O=C1CC(C(=O)OCC)CC(=O)C1=C(O)C1CC1 RVKCCVTVZORVGD-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11181635A EP2570404A1 (en) | 2011-09-16 | 2011-09-16 | Plant growth regulating compounds |
| PCT/EP2012/067706 WO2013037755A1 (en) | 2011-09-16 | 2012-09-11 | Plant growth regulating compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA201400348A1 EA201400348A1 (ru) | 2014-08-29 |
| EA024229B1 true EA024229B1 (ru) | 2016-08-31 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA201400348A EA024229B1 (ru) | 2011-09-16 | 2012-09-11 | Соединения, регулирующие рост растений |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US9345244B2 (enExample) |
| EP (2) | EP2570404A1 (enExample) |
| JP (1) | JP2014530179A (enExample) |
| KR (1) | KR20140062077A (enExample) |
| CN (1) | CN103796996A (enExample) |
| AR (1) | AR087851A1 (enExample) |
| AU (1) | AU2012307485A1 (enExample) |
| BR (1) | BR112014005980A2 (enExample) |
| CA (1) | CA2846779A1 (enExample) |
| CL (1) | CL2014000613A1 (enExample) |
| EA (1) | EA024229B1 (enExample) |
| IN (1) | IN2014DN01609A (enExample) |
| MX (1) | MX2014002852A (enExample) |
| PH (1) | PH12014500493A1 (enExample) |
| UY (1) | UY34323A (enExample) |
| WO (1) | WO2013037755A1 (enExample) |
| ZA (1) | ZA201401656B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201121539D0 (en) * | 2011-12-14 | 2012-01-25 | Syngenta Participations Ag | Plant growth regulating compounds |
| WO2014131735A1 (en) | 2013-02-28 | 2014-09-04 | Syngenta Participations Ag | Use of chemical compounds as herbicides |
| US10538522B2 (en) | 2015-05-14 | 2020-01-21 | The Regents Of The University Of California | Brassinosteroid mimetics |
| CN106831555B (zh) * | 2017-01-22 | 2019-09-24 | 中国农业大学 | 吡啶酰胺类化合物及其制备方法与应用 |
| US12357828B2 (en) | 2017-12-05 | 2025-07-15 | Ecole Polytechnique Federale De Lausanne (Epfl) | System for planning and/or providing neuromodulation |
| EP3827875B1 (en) | 2019-11-27 | 2023-07-05 | ONWARD Medical N.V. | Neuromodulation system |
| EP4206196A1 (en) | 2021-12-29 | 2023-07-05 | Almirall S.A. | Pyrimidine substituted derivatives as tyk2 inhibitors |
| CN114752608B (zh) * | 2022-04-24 | 2023-12-15 | 浙江大学 | 一种高含量油菜素内酯番茄植株的培育方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008049729A1 (en) * | 2006-10-12 | 2008-05-02 | Vib Vzw | Non-steroidal brassinosteroid mimetic |
| WO2009109570A1 (en) * | 2008-03-03 | 2009-09-11 | Gmi - Gregor-Mendel-Institut Für Molekulare Pflanzenbiologie Gmbh | Inhibitors for brassinosteroid signalling |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1275059A (en) * | 1968-11-12 | 1972-05-24 | Scottish Agricultural Ind Ltd | Method for stimulating the growth of plants |
| BR8600161A (pt) | 1985-01-18 | 1986-09-23 | Plant Genetic Systems Nv | Gene quimerico,vetores de plasmidio hibrido,intermediario,processo para controlar insetos em agricultura ou horticultura,composicao inseticida,processo para transformar celulas de plantas para expressar uma toxina de polipeptideo produzida por bacillus thuringiensis,planta,semente de planta,cultura de celulas e plasmidio |
| CA2005658A1 (en) | 1988-12-19 | 1990-06-19 | Eliahu Zlotkin | Insecticidal toxins, genes encoding these toxins, antibodies binding to them and transgenic plant cells and plants expressing these toxins |
| ES2074547T3 (es) | 1989-11-07 | 1995-09-16 | Pioneer Hi Bred Int | Lectinas larvicidas, y resistencia inducida de las plantas a los insectos. |
| UA48104C2 (uk) | 1991-10-04 | 2002-08-15 | Новартіс Аг | Фрагмент днк, який містить послідовність,що кодує інсектицидний протеїн, оптимізовану для кукурудзи,фрагмент днк, який забезпечує направлену бажану для серцевини стебла експресію зв'язаного з нею структурного гена в рослині, фрагмент днк, який забезпечує специфічну для пилку експресію зв`язаного з нею структурного гена в рослині, рекомбінантна молекула днк, спосіб одержання оптимізованої для кукурудзи кодуючої послідовності інсектицидного протеїну, спосіб захисту рослин кукурудзи щонайменше від однієї комахи-шкідника |
| US5530195A (en) | 1994-06-10 | 1996-06-25 | Ciba-Geigy Corporation | Bacillus thuringiensis gene encoding a toxin active against insects |
| JPH0881310A (ja) * | 1994-09-14 | 1996-03-26 | Sagami Chem Res Center | 植物生長調節剤 |
| EP1341903B1 (en) | 2000-12-07 | 2012-12-26 | Syngenta Limited | Plant derived hydroxy phenyl pyruvate dioxygneases (hppd) resistant against triketone herbicides and transgenic plants containing these dioxygenases |
| AR037856A1 (es) | 2001-12-17 | 2004-12-09 | Syngenta Participations Ag | Evento de maiz |
| GB0601744D0 (en) * | 2006-01-27 | 2006-03-08 | Novartis Ag | Organic compounds |
-
2011
- 2011-09-16 EP EP11181635A patent/EP2570404A1/en not_active Ceased
-
2012
- 2012-09-11 PH PH1/2014/500493A patent/PH12014500493A1/en unknown
- 2012-09-11 BR BR112014005980A patent/BR112014005980A2/pt not_active IP Right Cessation
- 2012-09-11 KR KR1020147007567A patent/KR20140062077A/ko not_active Withdrawn
- 2012-09-11 EA EA201400348A patent/EA024229B1/ru not_active IP Right Cessation
- 2012-09-11 CN CN201280044745.7A patent/CN103796996A/zh active Pending
- 2012-09-11 IN IN1609DEN2014 patent/IN2014DN01609A/en unknown
- 2012-09-11 WO PCT/EP2012/067706 patent/WO2013037755A1/en not_active Ceased
- 2012-09-11 AU AU2012307485A patent/AU2012307485A1/en not_active Abandoned
- 2012-09-11 US US14/344,765 patent/US9345244B2/en not_active Expired - Fee Related
- 2012-09-11 MX MX2014002852A patent/MX2014002852A/es unknown
- 2012-09-11 CA CA2846779A patent/CA2846779A1/en not_active Abandoned
- 2012-09-11 JP JP2014530176A patent/JP2014530179A/ja active Pending
- 2012-09-11 EP EP12758846.5A patent/EP2755951A1/en not_active Withdrawn
- 2012-09-13 UY UY0001034323A patent/UY34323A/es not_active Application Discontinuation
- 2012-09-13 AR ARP120103362A patent/AR087851A1/es unknown
-
2014
- 2014-03-05 ZA ZA2014/01656A patent/ZA201401656B/en unknown
- 2014-03-13 CL CL2014000613A patent/CL2014000613A1/es unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008049729A1 (en) * | 2006-10-12 | 2008-05-02 | Vib Vzw | Non-steroidal brassinosteroid mimetic |
| WO2009109570A1 (en) * | 2008-03-03 | 2009-09-11 | Gmi - Gregor-Mendel-Institut Für Molekulare Pflanzenbiologie Gmbh | Inhibitors for brassinosteroid signalling |
Non-Patent Citations (2)
| Title |
|---|
| DATABASE REGISTRY [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 8 September 2009 (2009-09-08), XP002662019, retrieved from STN Database accession no. 1181342-17-5 CAS Registry Numbers 1181342-17-5, 1181342-12-0, 1181285-46-0, 1181285-44-8 1181285-32-4, 1181275-89-7, 1181251-74-0, 1181251-73-9, 1181251-72-8, 1181251-71-7, 1181251-70-6, 1181251-68-2 * |
| DATABASE REGISTRY [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 9 September 2011 (2011-09-09), XP002662018, retrieved from STN, Database accession no. 1181390-80-6 CAS Registry Numbers 1181390-80-6, 1181390-77-1, 1181390-75-9, 1181390-74-8, 1181390-71-5, 1181383-84-5, 1181383-75-4 * |
Also Published As
| Publication number | Publication date |
|---|---|
| MX2014002852A (es) | 2014-04-10 |
| ZA201401656B (en) | 2015-06-24 |
| PH12014500493A1 (en) | 2014-04-14 |
| WO2013037755A1 (en) | 2013-03-21 |
| AU2012307485A1 (en) | 2014-04-03 |
| CA2846779A1 (en) | 2013-03-21 |
| US9345244B2 (en) | 2016-05-24 |
| EP2570404A1 (en) | 2013-03-20 |
| UY34323A (es) | 2013-04-30 |
| IN2014DN01609A (enExample) | 2015-05-15 |
| AR087851A1 (es) | 2014-04-23 |
| EA201400348A1 (ru) | 2014-08-29 |
| EP2755951A1 (en) | 2014-07-23 |
| BR112014005980A2 (pt) | 2017-04-04 |
| CL2014000613A1 (es) | 2014-10-10 |
| JP2014530179A (ja) | 2014-11-17 |
| US20150005167A1 (en) | 2015-01-01 |
| KR20140062077A (ko) | 2014-05-22 |
| CN103796996A (zh) | 2014-05-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): AM AZ BY KZ KG TJ TM RU |