IE43851B1 - Substituted piperidines and pyridines and their use as herbicides - Google Patents
Substituted piperidines and pyridines and their use as herbicidesInfo
- Publication number
- IE43851B1 IE43851B1 IE1295/76A IE129576A IE43851B1 IE 43851 B1 IE43851 B1 IE 43851B1 IE 1295/76 A IE1295/76 A IE 1295/76A IE 129576 A IE129576 A IE 129576A IE 43851 B1 IE43851 B1 IE 43851B1
- Authority
- IE
- Ireland
- Prior art keywords
- compounds
- methyl
- pyridinone
- phenyl
- dihydro
- Prior art date
Links
- 239000004009 herbicide Substances 0.000 title abstract description 11
- 150000003053 piperidines Chemical class 0.000 title description 2
- 150000003222 pyridines Chemical class 0.000 title description 2
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 17
- 239000004480 active ingredient Substances 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 321
- -1 phenoxy, phenylthio Chemical group 0.000 claims description 62
- 239000000203 mixture Substances 0.000 claims description 57
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000001153 fluoro group Chemical group F* 0.000 claims description 21
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 20
- 125000001246 bromo group Chemical group Br* 0.000 claims description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- 230000008569 process Effects 0.000 claims description 13
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical compound O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 6
- OVVCXAPQRAUKRK-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-methyl-5-[3-(trifluoromethyl)phenyl]-2,3-dihydropyridin-4-one Chemical compound C=1N(C)CC(C=2C=CC(Cl)=CC=2)C(=O)C=1C1=CC=CC(C(F)(F)F)=C1 OVVCXAPQRAUKRK-UHFFFAOYSA-N 0.000 claims description 4
- 239000004411 aluminium Substances 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- VRWBDTPZJOEALB-UHFFFAOYSA-N 1-methyl-3-(3-methylphenyl)-5-phenyl-2,3-dihydropyridin-4-one Chemical compound C=1N(C)CC(C=2C=C(C)C=CC=2)C(=O)C=1C1=CC=CC=C1 VRWBDTPZJOEALB-UHFFFAOYSA-N 0.000 claims description 2
- PVJXUIUFKMURFD-UHFFFAOYSA-N 1-methyl-5-(3-methylphenyl)-3-phenyl-2,3-dihydropyridin-4-one Chemical compound C=1N(C)CC(C=2C=CC=CC=2)C(=O)C=1C1=CC=CC(C)=C1 PVJXUIUFKMURFD-UHFFFAOYSA-N 0.000 claims description 2
- AVSUIEDSKCPYKV-UHFFFAOYSA-N 5-(4-fluorophenyl)-1-methyl-3-[3-(trifluoromethyl)phenyl]-2,3-dihydropyridin-4-one Chemical compound C=1N(C)CC(C=2C=C(C=CC=2)C(F)(F)F)C(=O)C=1C1=CC=C(F)C=C1 AVSUIEDSKCPYKV-UHFFFAOYSA-N 0.000 claims description 2
- 229910000091 aluminium hydride Inorganic materials 0.000 claims description 2
- 229910010277 boron hydride Inorganic materials 0.000 claims description 2
- PWNAVYNBODYLMS-UHFFFAOYSA-N 1-methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]-2,3-dihydropyridin-4-one Chemical compound C=1N(C)CC(C=2C=CC=CC=2)C(=O)C=1C1=CC=CC(C(F)(F)F)=C1 PWNAVYNBODYLMS-UHFFFAOYSA-N 0.000 claims 1
- 239000012141 concentrate Substances 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 60
- 238000012360 testing method Methods 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 23
- 239000000047 product Substances 0.000 description 23
- 239000002689 soil Substances 0.000 description 22
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000003795 chemical substances by application Substances 0.000 description 18
- 239000000543 intermediate Substances 0.000 description 18
- 238000004949 mass spectrometry Methods 0.000 description 17
- 239000012280 lithium aluminium hydride Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 13
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- 150000005299 pyridinones Chemical class 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 11
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical class O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000006170 formylation reaction Methods 0.000 description 8
- 150000002576 ketones Chemical class 0.000 description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000022244 formylation Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 4
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- QSURMNTYIIOVHX-UHFFFAOYSA-N 3,5-diphenyl-1h-pyridin-4-one Chemical compound O=C1C(C=2C=CC=CC=2)=CNC=C1C1=CC=CC=C1 QSURMNTYIIOVHX-UHFFFAOYSA-N 0.000 description 3
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 3
- 235000004135 Amaranthus viridis Nutrition 0.000 description 3
- 235000009344 Chenopodium album Nutrition 0.000 description 3
- 235000005484 Chenopodium berlandieri Nutrition 0.000 description 3
- 235000009332 Chenopodium rubrum Nutrition 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 3
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003905 agrochemical Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 150000004678 hydrides Chemical class 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 235000015097 nutrients Nutrition 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- GHJOIYGCNIDYAC-UHFFFAOYSA-N 1-methyl-5-phenyl-3-[3-(trifluoromethyl)phenyl]-2,3-dihydropyridin-4-one Chemical compound C=1N(C)CC(C=2C=C(C=CC=2)C(F)(F)F)C(=O)C=1C1=CC=CC=C1 GHJOIYGCNIDYAC-UHFFFAOYSA-N 0.000 description 2
- 240000000005 Chenopodium berlandieri Species 0.000 description 2
- 235000005853 Cyperus esculentus Nutrition 0.000 description 2
- 240000001505 Cyperus odoratus Species 0.000 description 2
- 244000152970 Digitaria sanguinalis Species 0.000 description 2
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 229940075894 denatured ethanol Drugs 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 230000008570 general process Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 125000001475 halogen functional group Chemical group 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000004452 microanalysis Methods 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical class CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- YFKBXYGUSOXJGS-UHFFFAOYSA-N 1,3-Diphenyl-2-propanone Chemical compound C=1C=CC=CC=1CC(=O)CC1=CC=CC=C1 YFKBXYGUSOXJGS-UHFFFAOYSA-N 0.000 description 1
- PIGAWZOZHAFCJZ-UHFFFAOYSA-N 1,3-bis(3-chlorophenyl)propan-2-one Chemical compound ClC1=CC=CC(CC(=O)CC=2C=C(Cl)C=CC=2)=C1 PIGAWZOZHAFCJZ-UHFFFAOYSA-N 0.000 description 1
- RKUAIEMXEVLDSJ-UHFFFAOYSA-N 1-(2-chlorophenyl)-3-[3-(trifluoromethyl)phenyl]propan-2-one Chemical compound FC(F)(F)C1=CC=CC(CC(=O)CC=2C(=CC=CC=2)Cl)=C1 RKUAIEMXEVLDSJ-UHFFFAOYSA-N 0.000 description 1
- RNWLDHSVJMHHKJ-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[3-(trifluoromethyl)phenyl]propan-2-one Chemical compound FC(F)(F)C1=CC=CC(CC(=O)CC=2C=CC(Cl)=CC=2)=C1 RNWLDHSVJMHHKJ-UHFFFAOYSA-N 0.000 description 1
- QGWDTWSVEFKPHY-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-[3-(trifluoromethyl)phenyl]propan-2-one Chemical compound C1=CC(F)=CC=C1CC(=O)CC1=CC=CC(C(F)(F)F)=C1 QGWDTWSVEFKPHY-UHFFFAOYSA-N 0.000 description 1
- YBTBLUIZFVXVOK-UHFFFAOYSA-N 1-but-1-enylpiperidine Chemical compound CCC=CN1CCCCC1 YBTBLUIZFVXVOK-UHFFFAOYSA-N 0.000 description 1
- LXTHYGMCWXCTEB-UHFFFAOYSA-N 1-ethenyl-3-(3-ethoxyphenyl)-5-(2-methylpropylsulfanyl)piperidin-4-one Chemical compound CCOC1=CC=CC(C2C(C(SCC(C)C)CN(C2)C=C)=O)=C1 LXTHYGMCWXCTEB-UHFFFAOYSA-N 0.000 description 1
- PZHIWRCQKBBTOW-UHFFFAOYSA-N 1-ethoxybutane Chemical compound CCCCOCC PZHIWRCQKBBTOW-UHFFFAOYSA-N 0.000 description 1
- NVJUHMXYKCUMQA-UHFFFAOYSA-N 1-ethoxypropane Chemical compound CCCOCC NVJUHMXYKCUMQA-UHFFFAOYSA-N 0.000 description 1
- CJAJLKYNOFHNLF-UHFFFAOYSA-N 1-methyl-3,5-bis[3-(trifluoromethyl)phenyl]-2,3-dihydropyridin-4-one Chemical compound C=1N(C)CC(C=2C=C(C=CC=2)C(F)(F)F)C(=O)C=1C1=CC=CC(C(F)(F)F)=C1 CJAJLKYNOFHNLF-UHFFFAOYSA-N 0.000 description 1
- PVMGDJVUYFHZES-UHFFFAOYSA-N 1-methyl-3,5-diphenylpiperidin-4-one Chemical class C1N(C)CC(C=2C=CC=CC=2)C(=O)C1C1=CC=CC=C1 PVMGDJVUYFHZES-UHFFFAOYSA-N 0.000 description 1
- PFQTVAHBUYEDNS-UHFFFAOYSA-N 1-methyl-3-[3-(trifluoromethyl)phenyl]piperidin-4-one Chemical compound C1N(C)CCC(=O)C1C1=CC=CC(C(F)(F)F)=C1 PFQTVAHBUYEDNS-UHFFFAOYSA-N 0.000 description 1
- FEVJJJQOPGZSIG-UHFFFAOYSA-N 2-[3-(trifluoromethyl)phenyl]acetyl chloride Chemical compound FC(F)(F)C1=CC=CC(CC(Cl)=O)=C1 FEVJJJQOPGZSIG-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 description 1
- FMKVJFMYKQKHRA-UHFFFAOYSA-N 3,5-bis(3-chlorophenyl)-1-methylpyridin-4-one Chemical compound O=C1C(C=2C=C(Cl)C=CC=2)=CN(C)C=C1C1=CC=CC(Cl)=C1 FMKVJFMYKQKHRA-UHFFFAOYSA-N 0.000 description 1
- LMGGTKVFSIJNDZ-UHFFFAOYSA-N 3,5-bis(3-fluorophenyl)-1-methylpiperidin-4-one Chemical compound C1N(C)CC(C=2C=C(F)C=CC=2)C(=O)C1C1=CC=CC(F)=C1 LMGGTKVFSIJNDZ-UHFFFAOYSA-N 0.000 description 1
- GYDWVYZQNXOGLJ-UHFFFAOYSA-N 3,5-diphenylpiperidin-2-one Chemical class O=C1NCC(C=2C=CC=CC=2)CC1C1=CC=CC=C1 GYDWVYZQNXOGLJ-UHFFFAOYSA-N 0.000 description 1
- JOTAMMMRYKLWBB-UHFFFAOYSA-N 3,5-diphenylpyran-4-one Chemical compound O=C1C(C=2C=CC=CC=2)=COC=C1C1=CC=CC=C1 JOTAMMMRYKLWBB-UHFFFAOYSA-N 0.000 description 1
- ZZBXHJIJTJTDQZ-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-methyl-5-[3-(trifluoromethyl)phenyl]piperidin-4-one Chemical compound C1N(C)CC(C=2C=C(C=CC=2)C(F)(F)F)C(=O)C1C1=CC=CC=C1Cl ZZBXHJIJTJTDQZ-UHFFFAOYSA-N 0.000 description 1
- GGZDJALKLYSDCA-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-methyl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound O=C1C(C=2C(=CC=CC=2)Cl)=CN(C)C=C1C1=CC=CC(C(F)(F)F)=C1 GGZDJALKLYSDCA-UHFFFAOYSA-N 0.000 description 1
- OUGBJIAJQIWLIH-UHFFFAOYSA-N 3-(2-chlorophenyl)-5-(3-chlorophenyl)-1-prop-2-ynyl-2,3-dihydropyridin-4-one Chemical compound ClC1=CC=CC(C=2C(C(CN(CC#C)C=2)C=2C(=CC=CC=2)Cl)=O)=C1 OUGBJIAJQIWLIH-UHFFFAOYSA-N 0.000 description 1
- HHCXPHJRNJVPOH-UHFFFAOYSA-N 3-(2-fluorophenyl)-5-(3-fluorophenyl)-1-methylpiperidin-4-one Chemical compound C1N(C)CC(C=2C=C(F)C=CC=2)C(=O)C1C1=CC=CC=C1F HHCXPHJRNJVPOH-UHFFFAOYSA-N 0.000 description 1
- HTZZAUNQHDRLCB-UHFFFAOYSA-N 3-(3-bromophenyl)-1-ethyl-5-phenylsulfanylpiperidin-4-one Chemical compound O=C1C(C=2C=C(Br)C=CC=2)CN(CC)CC1SC1=CC=CC=C1 HTZZAUNQHDRLCB-UHFFFAOYSA-N 0.000 description 1
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- 235000009869 Solanum phureja Nutrition 0.000 description 1
- 235000000341 Solanum ptychanthum Nutrition 0.000 description 1
- 235000017622 Solanum xanthocarpum Nutrition 0.000 description 1
- 240000003829 Sorghum propinquum Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
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- 240000003307 Zinnia violacea Species 0.000 description 1
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- XPOLVIIHTDKJRY-UHFFFAOYSA-N acetic acid;methanimidamide Chemical compound NC=N.CC(O)=O XPOLVIIHTDKJRY-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 235000003484 annual ragweed Nutrition 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 229910021641 deionized water Inorganic materials 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- CRPOUZQWHJYTMS-UHFFFAOYSA-N dialuminum;magnesium;disilicate Chemical compound [Mg+2].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] CRPOUZQWHJYTMS-UHFFFAOYSA-N 0.000 description 1
- AVGAIPMGSIOHFZ-UHFFFAOYSA-N dichloromethane;2-propan-2-yloxypropane Chemical compound ClCCl.CC(C)OC(C)C AVGAIPMGSIOHFZ-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
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- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000013067 intermediate product Substances 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
- 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
- 239000010410 layer Substances 0.000 description 1
- 235000019357 lignosulphonate Nutrition 0.000 description 1
- MXIRPJHGXWFUAE-UHFFFAOYSA-N lithium;propan-1-olate Chemical compound [Li+].CCC[O-] MXIRPJHGXWFUAE-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- HNPCDFJZADHNHD-UHFFFAOYSA-N n-(diformamidomethyl)formamide Chemical class O=CNC(NC=O)NC=O HNPCDFJZADHNHD-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- JUKHVNMXKSHNQY-UHFFFAOYSA-N penta-3,4-dien-2-one Chemical compound CC(=O)C=C=C JUKHVNMXKSHNQY-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000001308 synthesis method Methods 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/86—Oxygen 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/68—One oxygen atom attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59309575A | 1975-07-03 | 1975-07-03 | |
| US05/685,409 US4065290A (en) | 1975-07-03 | 1976-05-20 | Herbicidal β-phenyl-4-piperidinones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE43851L IE43851L (en) | 1977-01-03 |
| IE43851B1 true IE43851B1 (en) | 1981-06-17 |
Family
ID=27081623
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1295/76A IE43851B1 (en) | 1975-07-03 | 1976-06-15 | Substituted piperidines and pyridines and their use as herbicides |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS527970A (enExample) |
| AU (1) | AU497882B2 (enExample) |
| BR (1) | BR7604362A (enExample) |
| CA (1) | CA1088543A (enExample) |
| CH (2) | CH624273A5 (enExample) |
| DE (1) | DE2628992A1 (enExample) |
| ES (1) | ES449530A1 (enExample) |
| FR (1) | FR2315851A1 (enExample) |
| GB (1) | GB1555966A (enExample) |
| GR (1) | GR62256B (enExample) |
| IE (1) | IE43851B1 (enExample) |
| IL (1) | IL49858A (enExample) |
| IT (1) | IT1065058B (enExample) |
| NL (1) | NL7607421A (enExample) |
| OA (1) | OA05373A (enExample) |
| PT (1) | PT65313B (enExample) |
| SU (2) | SU691060A3 (enExample) |
| TR (1) | TR18922A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2720612C2 (de) * | 1977-05-07 | 1987-02-19 | Basf Ag, 6700 Ludwigshafen | 3,5-Dimethyl-piperidin-4-one |
| US4808720A (en) * | 1986-06-09 | 1989-02-28 | Stauffer Chemical Company | Certain 3-benzoyl-4-oxolactams |
-
1976
- 1976-06-14 CA CA254,796A patent/CA1088543A/en not_active Expired
- 1976-06-15 GR GR51000A patent/GR62256B/el unknown
- 1976-06-15 IE IE1295/76A patent/IE43851B1/en unknown
- 1976-06-22 IL IL49858A patent/IL49858A/xx unknown
- 1976-06-28 GB GB26770/76A patent/GB1555966A/en not_active Expired
- 1976-06-28 DE DE19762628992 patent/DE2628992A1/de not_active Withdrawn
- 1976-07-01 OA OA55871A patent/OA05373A/xx unknown
- 1976-07-02 IT IT25001/76A patent/IT1065058B/it active
- 1976-07-02 SU SU762377702A patent/SU691060A3/ru active
- 1976-07-02 ES ES449530A patent/ES449530A1/es not_active Expired
- 1976-07-02 BR BR7604362A patent/BR7604362A/pt unknown
- 1976-07-02 CH CH851576A patent/CH624273A5/de not_active IP Right Cessation
- 1976-07-02 PT PT65313A patent/PT65313B/pt unknown
- 1976-07-02 AU AU15538/76A patent/AU497882B2/en not_active Expired
- 1976-07-02 TR TR18922A patent/TR18922A/xx unknown
- 1976-07-02 FR FR7620260A patent/FR2315851A1/fr active Granted
- 1976-07-03 JP JP51079407A patent/JPS527970A/ja active Pending
- 1976-07-05 NL NL7607421A patent/NL7607421A/xx not_active Application Discontinuation
-
1977
- 1977-02-17 SU SU772453148A patent/SU688126A3/ru active
-
1980
- 1980-04-25 CH CH322980A patent/CH624392A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| OA05373A (fr) | 1981-02-28 |
| CH624273A5 (en) | 1981-07-31 |
| ES449530A1 (es) | 1977-12-01 |
| JPS527970A (en) | 1977-01-21 |
| DE2628992A1 (de) | 1977-01-20 |
| BR7604362A (pt) | 1977-07-26 |
| AU497882B2 (en) | 1979-01-18 |
| CA1088543A (en) | 1980-10-28 |
| SU688126A3 (ru) | 1979-09-25 |
| IL49858A (en) | 1980-06-30 |
| GB1555966A (en) | 1979-11-14 |
| FR2315851A1 (fr) | 1977-01-28 |
| SU691060A3 (ru) | 1979-10-05 |
| NL7607421A (nl) | 1977-01-05 |
| AU1553876A (en) | 1978-01-05 |
| IT1065058B (it) | 1985-02-25 |
| PT65313B (en) | 1978-01-05 |
| IL49858A0 (en) | 1976-08-31 |
| PT65313A (en) | 1976-08-01 |
| IE43851L (en) | 1977-01-03 |
| FR2315851B1 (enExample) | 1978-05-05 |
| GR62256B (en) | 1979-03-19 |
| TR18922A (tr) | 1977-12-20 |
| CH624392A5 (en) | 1981-07-31 |
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