KR20040102153A - 제초제로서 사용되는 3-헤테로아릴 치환된 5-메틸옥시메틸이속사졸린 - Google Patents

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Publication number

KR20040102153A

KR20040102153A KR10-2004-7016988A KR20047016988A KR20040102153A KR 20040102153 A KR20040102153 A KR 20040102153A KR 20047016988 A KR20047016988 A KR 20047016988A KR 20040102153 A KR20040102153 A KR 20040102153A

Authority

KR

South Korea

Prior art keywords

alkyl

formula

alkoxy

amino

haloalkyl

Prior art date

2002-04-25

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Withdrawn

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• 239000004009 herbicide Substances 0.000 title claims description 7
• AMCUCJRYPFDOCU-UHFFFAOYSA-N 5-(methoxymethyl)-4,5-dihydro-1,2-oxazole Chemical class COCC1CC=NO1 AMCUCJRYPFDOCU-UHFFFAOYSA-N 0.000 title 1
• -1 benzo [1,3] dioxolanyl Chemical group 0.000 claims abstract description 903
• 150000001875 compounds Chemical class 0.000 claims abstract description 190
• 239000001257 hydrogen Substances 0.000 claims abstract description 114
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 114
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 74
• WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical class C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims abstract description 63
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 47
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 36
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 35
• 125000004434 sulfur atom Chemical group 0.000 claims abstract description 34
• 239000001301 oxygen Substances 0.000 claims abstract description 33
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 29
• 238000000034 method Methods 0.000 claims abstract description 25
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims abstract description 20
• 150000003839 salts Chemical class 0.000 claims abstract description 17
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 15
• 125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 5
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims abstract description 3
• 125000005605 benzo group Chemical group 0.000 claims abstract description 3
• 125000001544 thienyl group Chemical group 0.000 claims abstract description 3
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 85
• 125000001424 substituent group Chemical group 0.000 claims description 84
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 82
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 65
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 51
• 125000000623 heterocyclic group Chemical group 0.000 claims description 45
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 41
• 229910052736 halogen Inorganic materials 0.000 claims description 37
• 150000002367 halogens Chemical class 0.000 claims description 37
• 239000000203 mixture Substances 0.000 claims description 35
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 34
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 34
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
• 125000003118 aryl group Chemical group 0.000 claims description 22
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 20
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 18
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 17
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 16
• 150000002825 nitriles Chemical class 0.000 claims description 15
• 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 15
• 230000002363 herbicidal effect Effects 0.000 claims description 14
• 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 13
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 13
• 125000005002 aryl methyl group Chemical group 0.000 claims description 11
• 229910052799 carbon Inorganic materials 0.000 claims description 11
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 9
• 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 8
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
• 125000000335 thiazolyl group Chemical group 0.000 claims description 8
• 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims description 6
• 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims description 6
• 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 6
• 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 6
• 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims description 6
• 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 6
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 6
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 6
• 125000002541 furyl group Chemical group 0.000 claims description 6
• 125000002883 imidazolyl group Chemical group 0.000 claims description 6
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 6
• 230000000269 nucleophilic effect Effects 0.000 claims description 6
• 125000002971 oxazolyl group Chemical group 0.000 claims description 6
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
• JHCKZGSCVJRFHY-UHFFFAOYSA-N 3-methyl-4,5-dihydro-1,2-oxazole Chemical class CC1=NOCC1 JHCKZGSCVJRFHY-UHFFFAOYSA-N 0.000 claims description 5
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
• 150000004820 halides Chemical class 0.000 claims description 4
• 150000002547 isoxazolines Chemical class 0.000 claims description 4
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
• 239000011814 protection agent Substances 0.000 claims description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
• 239000002671 adjuvant Substances 0.000 claims description 3
• 238000002156 mixing Methods 0.000 claims description 3
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 3
• 239000011593 sulfur Substances 0.000 claims description 3
• PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 claims description 2
• 206010041349 Somnolence Diseases 0.000 claims description 2
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000005879 dioxolanyl group Chemical group 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims 3
• DIYXRDINNSPDFJ-UHFFFAOYSA-N 4,5-dihydro-1,3-oxazol-5-ylmethanol Chemical compound OCC1CN=CO1 DIYXRDINNSPDFJ-UHFFFAOYSA-N 0.000 claims 2
• 125000000217 alkyl group Chemical group 0.000 abstract description 8
• 125000001188 haloalkyl group Chemical group 0.000 abstract description 8
• 238000002360 preparation method Methods 0.000 abstract description 7
• 239000000543 intermediate Substances 0.000 abstract description 6
• 125000003107 substituted aryl group Chemical group 0.000 abstract 1
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 55
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 53
• 150000002431 hydrogen Chemical class 0.000 description 46
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 42
• 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 description 28
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 28
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 27
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 23
• XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 20
• 241000196324 Embryophyta Species 0.000 description 19
• 229910052757 nitrogen Inorganic materials 0.000 description 19
• 229910052794 bromium Inorganic materials 0.000 description 18
• 125000005842 heteroatom Chemical group 0.000 description 18
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 17
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 17
• 238000006243 chemical reaction Methods 0.000 description 17
• 239000000460 chlorine Substances 0.000 description 17
• 229910052801 chlorine Inorganic materials 0.000 description 17
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 16
• PHVFVPURCHVDBP-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazol-5-ylmethanol Chemical compound OCC1CC=NO1 PHVFVPURCHVDBP-UHFFFAOYSA-N 0.000 description 14
• 125000004076 pyridyl group Chemical group 0.000 description 14
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
• 229910052731 fluorine Inorganic materials 0.000 description 12
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 11
• 239000011737 fluorine Substances 0.000 description 11
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
• 239000002904 solvent Substances 0.000 description 10
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 10
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
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• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
• 239000002253 acid Chemical class 0.000 description 8
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 8
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• 125000001153 fluoro group Chemical group F* 0.000 description 7
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 7
• 238000011282 treatment Methods 0.000 description 7
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 6
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• 229910052783 alkali metal Inorganic materials 0.000 description 6
• RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
• 239000002585 base Substances 0.000 description 6
• 125000004432 carbon atom Chemical group C* 0.000 description 6
• 239000004359 castor oil Substances 0.000 description 6
• 235000019438 castor oil Nutrition 0.000 description 6
• ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 6
• 229910052740 iodine Inorganic materials 0.000 description 6
• 239000011630 iodine Substances 0.000 description 6
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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