CN1323292A - 苯甲酰基环己烷二酮,其制法,及其作为除草剂与植物生长调节剂的用途 - Google Patents
苯甲酰基环己烷二酮,其制法,及其作为除草剂与植物生长调节剂的用途 Download PDFInfo
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- CN1323292A CN1323292A CN99811954A CN99811954A CN1323292A CN 1323292 A CN1323292 A CN 1323292A CN 99811954 A CN99811954 A CN 99811954A CN 99811954 A CN99811954 A CN 99811954A CN 1323292 A CN1323292 A CN 1323292A
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- Prior art keywords
- carbonyl
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- alkyl
- oxygen
- amino
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- 238000000034 method Methods 0.000 title claims abstract description 18
- XKLPBDMZJSWRBL-UHFFFAOYSA-N 3-benzoylcyclohexane-1,2-dione Chemical class C=1C=CC=CC=1C(=O)C1CCCC(=O)C1=O XKLPBDMZJSWRBL-UHFFFAOYSA-N 0.000 title claims description 13
- 239000004009 herbicide Substances 0.000 title abstract description 7
- 238000004519 manufacturing process Methods 0.000 title abstract description 4
- 239000005648 plant growth regulator Substances 0.000 title abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 301
- 239000001301 oxygen Substances 0.000 claims description 293
- -1 halogen alkynes Chemical class 0.000 claims description 228
- 229910052736 halogen Inorganic materials 0.000 claims description 205
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 122
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 118
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 115
- 125000003118 aryl group Chemical group 0.000 claims description 114
- 150000002367 halogens Chemical class 0.000 claims description 96
- 125000001072 heteroaryl group Chemical group 0.000 claims description 91
- 150000001875 compounds Chemical class 0.000 claims description 83
- 150000001336 alkenes Chemical class 0.000 claims description 78
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 74
- 125000000217 alkyl group Chemical group 0.000 claims description 61
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 60
- 125000000623 heterocyclic group Chemical group 0.000 claims description 58
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 43
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 42
- MIQWEMDDUPSLRW-UHFFFAOYSA-N [O].O=C=O Chemical compound [O].O=C=O MIQWEMDDUPSLRW-UHFFFAOYSA-N 0.000 claims description 41
- 125000003545 alkoxy group Chemical group 0.000 claims description 41
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 40
- 125000000304 alkynyl group Chemical group 0.000 claims description 40
- 239000001257 hydrogen Substances 0.000 claims description 37
- 150000001345 alkine derivatives Chemical class 0.000 claims description 36
- 229910021529 ammonia Inorganic materials 0.000 claims description 36
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 34
- 125000002521 alkyl halide group Chemical group 0.000 claims description 33
- 239000000460 chlorine Substances 0.000 claims description 33
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 31
- 239000005864 Sulphur Substances 0.000 claims description 31
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 31
- 150000003254 radicals Chemical class 0.000 claims description 28
- 229910005965 SO 2 Inorganic materials 0.000 claims description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 27
- 230000000694 effects Effects 0.000 claims description 26
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 26
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 25
- 125000002252 acyl group Chemical group 0.000 claims description 25
- 125000005108 alkenylthio group Chemical group 0.000 claims description 25
- 125000004414 alkyl thio group Chemical group 0.000 claims description 25
- 239000005077 polysulfide Substances 0.000 claims description 25
- 229920001021 polysulfide Polymers 0.000 claims description 25
- 150000008117 polysulfides Polymers 0.000 claims description 25
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 23
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 23
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 21
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 21
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 18
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 17
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 16
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 16
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 16
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 15
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 15
- 125000005357 cycloalkylalkynyl group Chemical group 0.000 claims description 15
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 14
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 14
- 125000005312 heteroarylalkynyl group Chemical group 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 12
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 12
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 10
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 10
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 10
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000005087 alkynylcarbonyl group Chemical group 0.000 claims description 9
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 230000002363 herbicidal effect Effects 0.000 claims description 9
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 9
- 125000005222 heteroarylaminocarbonyl group Chemical group 0.000 claims description 9
- 238000009333 weeding Methods 0.000 claims description 9
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 8
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 8
- 125000006776 haloalkenylcarbonyl group Chemical group 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 7
- 125000005134 alkynylsulfinyl group Chemical group 0.000 claims description 7
- 125000005110 aryl thio group Chemical group 0.000 claims description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 125000006812 haloalkenylaminocarbonyl group Chemical group 0.000 claims description 7
- CXDHJGCWMIOAQP-UHFFFAOYSA-N 2-pyridin-3-yl-1,4,5,6-tetrahydropyrimidine;hydrochloride Chemical compound Cl.C1CCNC(C=2C=NC=CC=2)=N1 CXDHJGCWMIOAQP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003368 amide group Chemical group 0.000 claims description 6
- 125000005140 aralkylsulfonyl group Chemical group 0.000 claims description 6
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
- DIAYCDKWIYBLKQ-UHFFFAOYSA-N [O].NS(N)(=O)=O Chemical compound [O].NS(N)(=O)=O DIAYCDKWIYBLKQ-UHFFFAOYSA-N 0.000 claims description 5
- SDBBVRRHEFMBQR-UHFFFAOYSA-N [O]C1CCCS1 Chemical compound [O]C1CCCS1 SDBBVRRHEFMBQR-UHFFFAOYSA-N 0.000 claims description 5
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 5
- 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 claims description 5
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 5
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 5
- 125000005224 heteroarylcarbonylamino group Chemical group 0.000 claims description 5
- 125000005150 heteroarylsulfinyl group Chemical group 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 239000011630 iodine Substances 0.000 claims description 5
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 claims description 5
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
- MIMNPERXMRSLHR-UHFFFAOYSA-N [O]C1CCSC1 Chemical compound [O]C1CCSC1 MIMNPERXMRSLHR-UHFFFAOYSA-N 0.000 claims description 4
- 239000012752 auxiliary agent Substances 0.000 claims description 4
- 125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims description 4
- 125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 239000011574 phosphorus Substances 0.000 claims description 4
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims description 4
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 150000001350 alkyl halides Chemical class 0.000 claims description 3
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 3
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 125000004647 alkyl sulfenyl group Chemical group 0.000 claims description 2
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 150000001555 benzenes Chemical class 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 2
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
- 244000038559 crop plants Species 0.000 claims 3
- 150000001924 cycloalkanes Chemical class 0.000 claims 3
- QECVIPBZOPUTRD-UHFFFAOYSA-N N=S(=O)=O Chemical compound N=S(=O)=O QECVIPBZOPUTRD-UHFFFAOYSA-N 0.000 claims 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- RZBWFMYMESYJDK-UHFFFAOYSA-N C(=O)=N.[O] Chemical compound C(=O)=N.[O] RZBWFMYMESYJDK-UHFFFAOYSA-N 0.000 claims 1
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 claims 1
- HPNGSNQUZJCURG-UHFFFAOYSA-N [O]C1OC=CC=C1 Chemical compound [O]C1OC=CC=C1 HPNGSNQUZJCURG-UHFFFAOYSA-N 0.000 claims 1
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims 1
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- SDFDEKLHKAQRHH-UHFFFAOYSA-N 3,4-dihydronaphthalene-1,2-dione Chemical class C1=CC=C2C(=O)C(=O)CCC2=C1 SDFDEKLHKAQRHH-UHFFFAOYSA-N 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 239000002585 base Substances 0.000 description 283
- 241000196324 Embryophyta Species 0.000 description 64
- 239000013543 active substance Substances 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 22
- 239000000126 substance Substances 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
- 150000002148 esters Chemical class 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- 108090000623 proteins and genes Proteins 0.000 description 15
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 13
- 239000004615 ingredient Substances 0.000 description 13
- 239000000463 material Substances 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 238000001035 drying Methods 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 125000005225 alkynyloxycarbonyl group Chemical group 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 244000025254 Cannabis sativa Species 0.000 description 9
- 239000000428 dust Substances 0.000 description 9
- 244000037671 genetically modified crops Species 0.000 description 9
- 239000002689 soil Substances 0.000 description 9
- 239000004562 water dispersible granule Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- 150000001721 carbon Chemical group 0.000 description 8
- 239000004495 emulsifiable concentrate Substances 0.000 description 8
- 230000008635 plant growth Effects 0.000 description 8
- 240000007594 Oryza sativa Species 0.000 description 7
- 235000007164 Oryza sativa Nutrition 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 230000002650 habitual effect Effects 0.000 description 7
- 230000001473 noxious effect Effects 0.000 description 7
- 235000009566 rice Nutrition 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000005090 alkenylcarbonyl group Chemical group 0.000 description 6
- 235000010233 benzoic acid Nutrition 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 230000012010 growth Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 6
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 5
- 244000237956 Amaranthus retroflexus Species 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 240000003173 Drymaria cordata Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 5
- 125000006356 alkylene carbonyl group Chemical group 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
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- 230000006872 improvement Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229940095102 methyl benzoate Drugs 0.000 description 5
- 150000004702 methyl esters Chemical class 0.000 description 5
- 230000001105 regulatory effect Effects 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 4
- 239000005995 Aluminium silicate Substances 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 4
- 241000234653 Cyperus Species 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000003905 agrochemical Substances 0.000 description 4
- 125000005139 alkynylsulfonyl group Chemical group 0.000 description 4
- 235000012211 aluminium silicate Nutrition 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 4
- VAIZTNZGPYBOGF-UHFFFAOYSA-N butyl 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate Chemical compound C1=CC(OC(C)C(=O)OCCCC)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 VAIZTNZGPYBOGF-UHFFFAOYSA-N 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
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- 125000001424 substituent group Chemical group 0.000 description 4
- 230000009261 transgenic effect Effects 0.000 description 4
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- 239000003643 water by type Substances 0.000 description 4
- 235000016068 Berberis vulgaris Nutrition 0.000 description 3
- 241000335053 Beta vulgaris Species 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- 108020004414 DNA Proteins 0.000 description 3
- 244000058871 Echinochloa crus-galli Species 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- 239000005562 Glyphosate Substances 0.000 description 3
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- WJNRPILHGGKWCK-UHFFFAOYSA-N propazine Chemical compound CC(C)NC1=NC(Cl)=NC(NC(C)C)=N1 WJNRPILHGGKWCK-UHFFFAOYSA-N 0.000 description 1
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PHNUZKMIPFFYSO-UHFFFAOYSA-N propyzamide Chemical compound C#CC(C)(C)NC(=O)C1=CC(Cl)=CC(Cl)=C1 PHNUZKMIPFFYSO-UHFFFAOYSA-N 0.000 description 1
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- FKERUJTUOYLBKB-UHFFFAOYSA-N pyrazoxyfen Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OCC(=O)C1=CC=CC=C1 FKERUJTUOYLBKB-UHFFFAOYSA-N 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 description 1
- OSUHJPCHFDQAIT-GFCCVEGCSA-N quizalofop-P-ethyl Chemical group C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 OSUHJPCHFDQAIT-GFCCVEGCSA-N 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000008521 reorganization Effects 0.000 description 1
- 230000000452 restraining effect Effects 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- BCQMBFHBDZVHKU-UHFFFAOYSA-N terbumeton Chemical compound CCNC1=NC(NC(C)(C)C)=NC(OC)=N1 BCQMBFHBDZVHKU-UHFFFAOYSA-N 0.000 description 1
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical class OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical class CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004549 water soluble granule Substances 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- A01N43/80—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 one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/24—Sulfones; Sulfoxides having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D309/06—Radicals substituted by oxygen atoms
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4056—Esters of arylalkanephosphonic acids
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- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
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- C07C2601/14—The ring being saturated
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- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
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- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Indole Compounds (AREA)
- Furan Compounds (AREA)
- Pyrane Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Abstract
Description
实施例编号 | R1 | R7 | 物性数据 |
27 | OCH2CHF2 | Me | |
28 | SCH2CF3 | H | |
29 | SCH2CF3 | Me |
实施例编号 | R7a | R7b | R12 | L | R1 |
30 | H | H | Bz | CH2 | 0-环己基 |
31 | H | Me | Bz | CH2 | 0-环己基 |
32 | Me | Me | Bz | CH2 | 0-环己基 |
33 | H | H | PhC(O)CH2 | CH2 | 0-环己基 |
34 | H | Me | PhC(O)CH2 | CH2 | 0-环己基 |
35 | Me | Me | PhC(O)CH2 | CH2 | 0-环己基 |
36 | H | H | 4-Me-Bz | CH2 | 0-环己基 |
37 | H | Me | 4-Me-Bz | CH2 | 0-环己基 |
38 | Me | Me | 4-Me-Bz | CH2 | 0-环戊基 |
39 | H | H | MeSO2 | CH2 | 0-环己基 |
40 | H | Me | MeSO2 | CH2 | 0-环己基 |
41 | Me | Me | MeSO2 | CH2 | 0-环己基 |
42 | H | H | EtSO2 | CH2 | 0-环己基 |
43 | H | Me | EtSO2 | CH2 | O-环己基 |
44 | Me | Me | EtSO2 | CH2 | 0-环己基 |
实施例编号 | R7a | R7b | R12 | L | R1 |
45 | H | H | PrSO2 | CH2 | 0-环己基 |
46 | H | Me | PrSO2 | CH2 | 0-环己基 |
47 | Me | Me | PrSO2 | CH2 | 0-环己基 |
48 | H | H | PhSO2 | CH2 | 0-环己基 |
49 | H | Me | PhSO2 | CH2 | 0-环己基 |
50 | Me | Me | PhSO2 | CH2 | 0-环己基 |
51 | H | H | 4-Me-PhSO2 | CH2 | 0-环己基 |
52 | H | Me | 4-Me-PhSO2 | CH2 | 0-环己基 |
53 | Me | Me | 4-Me-PhSO2 | CH2 | 0-环己基 |
54 | H | H | Bz | CH2 | 0-环戊基 |
55 | H | Me | Bz | CH2 | 0-环戊基 |
56 | Me | Me | Bz | CH2 | 0-环戊基 |
57 | H | H | PhC(O)CH2 | CH2 | 0-环戊基 |
58 | H | Me | PhC(O)CH2 | CH2 | 0-环戊基 |
59 | Me | Me | PhC(O)CH2 | CH2 | 0-环戊基 |
60 | H | H | 4-Me-Bz | CH2 | 0-环戊基 |
61 | H | Me | 4-Me-Bz | CH2 | 0-环戊基 |
62 | Me | Me | 4-Me-Bz | CH2 | 0-环戊基 |
63 | H | H | MeSO2 | CH2 | 0-环戊基 |
64 | H | Me | MeSO2 | CH2 | 0-环戊基 |
65 | Me | Me | MeSO2 | CH2 | 0-环戊基 |
66 | H | H | EtSO2 | CH2 | 0-环戊基 |
67 | H | Me | EtSO2 | CH2 | 0-环戊基 |
68 | Me | Me | EtSO2 | CH2 | 0-环戊基 |
69 | H | H | PrSO2 | CH2 | 0-环戊基 |
70 | H | Me | PrSO2 | CH2 | 0-环戊基 |
实施例编号 | R7a | R7b | R12 | L | R1 |
71 | Me | Me | prSO2 | CH2 | 0-环戊基 |
72 | H | H | PhSO2 | CH2 | 0-环戊基 |
73 | H | Me | PhSO2 | CH2 | 0-环戊基 |
74 | Me | Me | phSO2 | CH2 | 0-环戊基 |
75 | H | H | 4-Me-PhSO2 | CH2 | 0-环戊基 |
76 | H | Me | 4-Me-PhSO2 | CH2 | 0-环戊基 |
77 | Me | Me | 4-Me-PhSO2 | CH2 | 0-环戊基 |
78 | H | H | Bz | CH2 | O-c-Bu |
79 | H | Me | Bz | CH2 | O-c-Bu |
80 | Me | Me | Bz | CH2 | O-c-Bu |
81 | H | H | PhC(O)CH2 | CH2 | O-c-Bu |
82 | H | Me | PhC(O)CH2 | CH2 | O-c-Bu |
83 | Me | Me | PhC(O)CH2 | CH2 | O-c-Bu |
84 | H | H | 4-Me-Bz | CH2 | O-c-Bu |
85 | H | Me | 4-Me-Bz | CH2 | O-c-Bu |
B6 | Me | Me | 4-Me-Bz | CH2 | O-c-Bu |
87 | H | H | MeSO2 | CH2 | O-c-Bu |
88 | H | Me | MeSO2 | CH2 | O-c-Bu |
89 | Me | Me | MeSO2 | CH2 | O-c-Bu |
90 | H | H | EtSO2 | CH2 | O-c-Bu |
91 | H | Me | EtSO2 | CH2 | O-c-Bu |
92 | Me | Me | EtSO2 | CH2 | O-c-Bu |
93 | H | H | PrSO2 | CH2 | O-c-Bu |
94 | H | Me | PrSO2 | CH2 | O-c-Bu |
95 | Me | Me | PrSO2 | CH2 | O-c-Bu |
96 | H | H | PhSO2 | CH2 | O-c-Bu |
97 | H | Me | PhSO2 | CH2 | O-c-Bu |
实施例编号 | R7a | R7b | R12 | L | R1 |
98 | Me | Me | phSO2 | CH2 | O-c-Bu |
99 | H | H | 4-Me-PhSO2 | CH2 | O-c-Bu |
100 | H | Me | 4-Me-PhSO2 | CH2 | O-c-Bu |
101 | Me | Me | 4-Me-PhSO2 | CH2 | O-c-Bu |
102 | H | H | Bz | CH2 | O-c-Pr |
103 | H | Me | Bz | CH2 | O-c-Pr |
104 | Me | Me | Bz | CH2 | O-c-Pr |
105 | H | H | phC(O)CH2 | CH2 | O-c-Pr |
106 | H | Me | PhC(O)CH2 | CH2 | O-c-Pr |
107 | Me | Me | PhC(O)CH2 | CH2 | O-c-Pr |
108 | H | H | 4-Me-Bz | CH2 | O-c-Pr |
109 | H | Me | 4-Me-Bz | CH2 | O-c-Pr |
110 | Me | Me | 4-Me-Bz | CH2 | O-c-Pr |
111 | H | H | MeSO2 | CH2 | O-c-Pr |
112 | H | Me | MeSO2 | CH2 | O-c-Pr |
113 | Me | Me | MeSO2 | CHx | O-c-Pr |
114 | H | H | EtSO2 | CH2 | O-c-Pr |
115 | H | Me | EtSO2 | CH2 | O-c-Pr |
116 | Me | Me | EtSO2 | CH2 | O-c-Pr |
117 | H | H | PrSO2 | CH2 | O-c-Pr |
118 | H | Me | PrSO2 | CH2 | O-c-Pr |
119 | Me | Me | PrSO2 | CH2 | O-c-Pr |
120 | H | H | PhSO2 | CH2 | O-c-Pr |
121 | H | Me | PhSO2 | CH2 | O-c-Pr |
122 | Me | Me | PhSO2 | CH2 | O-c-Pr |
123 | H | H | 4-Me-PhSO2 | CH2 | O-c-Pr |
124 | H | Me | 4-Me-PhSO2 | CH2 | O-c-Pr |
实施例编号 | R7a | R7b | R12 | L | R1 |
125 | Me | Me | 4-Me-PhSO2 | CH2 | O-c-Pr |
126 | H | H | Bz | CH2 | OCH2CF3 |
127 | H | Me | Bz | CH2 | OCH2CF3 |
128 | Me | Me | Bz | CH2 | OCH2CF3 |
129 | H | H | PhC(O)CH2 | CH2 | OCH2CF3 |
130 | H | Me | PhC(O)CH2 | CH2 | OCH2CF3 |
131 | Me | Me | PhC(O)CH2 | CH2 | OCH2CF3 |
132 | H | H | 4-Me-Bz | CH2 | OCH2CF3 |
133 | H | Me | 4-Me-Bz | CH2 | OCH2CF3 |
134 | Me | Me | 4-Me-Bz | CH2 | OCH2CF3 |
135 | H | H | MeSO2 | CH2 | OCH2CF3 |
136 | H | Me | MeSO2 | CH2 | OCH2CF3 |
137 | Me | Me | MeSO2 | CH2 | OCH2CF3 |
138 | H | H | EtSO2 | CH2 | OCH2CF3 |
139 | H | Me | EtSO2 | CH2 | OCH2CF3 |
140 | Me | Me | EtSO2 | CH2 | OCH2CF3 |
141 | H | H | PrSO2 | CH2 | OCH2CF3 |
142 | H | Me | PrSO2 | CH2 | OCH2CF3 |
143 | Me | Me | PrSO2 | CH2 | OCH2CF3 |
144 | H | H | PhSO2 | CH2 | OCH2CF3 |
145 | H | Me | PhSO2 | CH2 | OCH2CF3 |
146 | Me | Me | PhSO2 | CH2 | OCH2CF3 |
147 | H | H | 4-Me-PhSO2 | CH2 | OCH2CF3 |
148 | H | Me | 4-Me-PhSO2 | CH2 | OCH2CF3 |
149 | Me | Me | 4-Me-PhSO2 | CH2 | OCH2CF3 |
150 | H | H | Bz | CH2CH2 | 0-环己基 |
151 | H | Me | Bz | CH2CH2 | 0-环己基 |
实施例编号 | R7a | R7b | R12 | L | R1 |
152 | Me | Me | Bz | CH2CH2 | 0-环己基 |
153 | H | H | PhC(O)CH2 | CH2CH2 | 0-环己基 |
154 | H | Me | PhC(O)CH2 | CH2CH2 | 0-环己基 |
155 | Me | Me | PhC(O)CH2 | CH2CH2 | 0-环己基 |
156 | H | H | 4-Me-Bz | CH2CH2 | 0-环己基 |
157 | H | Me | 4-Me-Bz | CH2CH2 | 0-环己基 |
158 | Me | Me | 4-Me-Bz | CH2CH2 | 0-环己基 |
159 | H | H | MeSO2 | CH2CH2 | 0-环己基 |
160 | H | Me | MeSO2 | CH2CH2 | 0-环己基 |
161 | Me | Me | MeSO2 | CH2CH2 | 0-环己基 |
162 | H | H | EtSO2 | CH2CH2 | 0-环己基 |
163 | H | Me | EtSO2 | CH2CH2 | 0-环己基 |
164 | Me | Me | EtSO2 | CH2CH2 | 0-环己基 |
165 | H | H | PrSO2 | CH2CH2 | 0-环己基 |
166 | H | Me | PrsO2 | CH2CH2 | 0-环己基 |
167 | Me | Me | PrSO2 | CH2CH2 | 0-环己基 |
168 | H | H | phSO2 | CH2CH2 | 0-环己基 |
169 | H | Me | PhSO2 | CH2CH2 | 0-环己基 |
170 | Me | Me | PhSO2 | CH2CH2 | 0-环己基 |
171 | H | H | 4-Me-PhSO2 | CH2CH2 | 0-环己基 |
172 | H | Me | 4-Me-PhSO2 | CH2CH2 | 0-环己基 |
173 | Me | Me | 4-Me-PhSO2 | CH2CH2 | 0-环己基 |
174 | H | H | Bz | CH2CH2 | 0-环戊基 |
175 | H | Me | Bz | CH2CH2 | 0-环戊基 |
176 | Me | Me | Bz | CH2CH2 | 0-环戊基 |
177 | H | H | PhC(O)CH2 | CH2CH2 | 0-环戊基 |
178 | H | Me | PhC(O)CH2 | CH2CH2 | 0-环戊基 |
实施例编号 | R7a | R7b | R12 | L | R1 |
179 | Me | Me | PhC(O)CH2 | CH2CH2 | 0-环戊基 |
180 | H | H | 4-Me-PhC(O) | CH2CH2 | 0-环戊基 |
181 | H | Me | 4-Me-PhC(O) | CH2CH2 | 0-环戊基1 |
182 | Me | Me | 4-Me-PhC(O) | CH2CH2 | 0-环戊基1 |
183 | H | H | MeSO2 | CH2CH2 | 0-环戊基1 |
184 | H | Me | MeSO2 | CH2CH2 | 0-环戊基1 |
185 | Me | Me | MeSO2 | CH2CH2 | 0-环戊基1 |
186 | H | H | EtSO2 | CH2CH2 | 0-环戊基 |
187 | H | Me | EtSO2 | CH2CH2 | 0-环戊基 |
188 | Me | Me | EtSO2 | CH2CH2 | 0-环戊基 |
189 | H | H | PrSO2 | CH2CH2 | 0-环戊基 |
190 | H | Me | PrSO2 | CH2CH2 | 0-环戊基1 |
191 | Me | Me | PrSO2 | CH2CH2 | 0-环戊基1 |
192 | H | H | PhSO2 | CH2CH2 | 0-环戊基1 |
193 | H | Me | PhSO2 | CH2CH2 | 0-环戊基1 |
194 | Me | Me | PhSO2 | CH2CH2 | 0-环戊基 |
195 | H | H | 4-Me-PhSO2 | CH2CH2 | 0-环戊基 |
196 | H | Me | 4-Me-PhSO2 | CH2CH2 | 0-环戊基1 |
197 | Me | Me | 4-Me-PhSO2 | CH2CH2 | 0-环戊基 |
198 | H | H | Bz | CH2CH2 | O-c-Bu |
199 | H | Me | Bz | CH2CH2 | O-c-Bu |
200 | Me | Me | Bz | CH2CH2 | O-c-Bu |
201 | H | H | PhC(O)CH2 | CH2CH2 | O-c-Bu |
202 | H | Me | PhC(O)CH2 | CH2CH2 | O-c-Bu |
203 | Me | Me | PhC(O)CH2 | CH2CH2 | O-c-Bu |
204 | H | H | 4-Me-Bz | CH2CH2 | O-c-Bu |
205 | H | Me | 4-Me-Bz | CH2CH2 | O-c-Bu |
实施例编号 | R7a | R7b | R12 | L | R1 | ||
206 | Me | Me | 4-Me-Bz | CH2CH2 | O-c-Bu | ||
207 | H | H | MeSO2 | CH2CH2 | O-c-Bu | ||
208 | H | Me | MeSO2 | CH2CH2 | O-c-Bu | ||
209 | Me | Me | MeSO2 | CH2CH2 | O-c-Bu | ||
210 | H | H | EtSO2 | CH2CH2 | O-c-Bu | ||
211 | H | Me | EtSO2 | CH2CH2 | O-c-Bu | ||
212 | Me | Me | EtSO2 | CH2CH2 | O-c-Bu | ||
213 | H | H | PrsO2 | CH2CH2 | O-c-Bu | ||
214 | H | Me | PrSO2 | CH2CH2 | O-c-Bu | ||
215 | Me | Me | PrSO2 | CH2CH2 | O-c-Bu | ||
216 | H | H | PhSO2 | CH2CH2 | O-c-Bu | ||
217 | H | Me | PhSO2 | CH2CH2 | O-c-Bu | ||
218 | Me | Me | PhSO2 | CH2CH2 | O-c-Bu | ||
219 | H | H | 4-Me-PhSO2 | CH2CH2 | O-c-Bu | ||
220 | H | Me | 4-Me-PhSO2 | CH2CH2 | O-c-Bu | ||
221 | Me | Me | 4-Me-PhSO2 | CH2CH2 | O-c-Bu | ||
222 | H | H | Bz | CH2CH2 | O-c-Pr | ||
223 | H | Me | Bz | CH2CH2 | O-c-Pr | ||
224 | Me | Me | Bz | CH2CH2 | O-c-Pr | ||
225 | H | H | PhC(O)CH2 | CH2CH2 | O-c-Pr | ||
226 | H | Me | PhC(O)CH2 | CH2CH2 | O-c-Pr | ||
227 | Me | Me | PhC(O)CH2 | CH2CH2 | O-c-Pr | ||
228 | H | H | 4-Me-Bz | CH2CH2 | O-c-Pr | ||
229 | H | Me | 4-Me-Bz | CH2CH2 | O-c-Pr | ||
230 | Me | Me | 4-Me-Bz | CH2CH2 | O-c-Pr | ||
231 | H | H | MeSO2 | CH2CH2 | O-c-Pr | ||
232 | H | Me | MeSO2 | CH2CH2 | O-c-Pr |
实施例编号 | R7a | R7b | R12 | L | R1 | ||
233 | Me | Me | MeSO2 | CH2CH2 | O-c-Pr | ||
234 | H | H | EtSO2 | CH2CH2 | O-c-Pr | ||
235 | H | Me | EtSO2 | CH2CH2 | O-c-Pr | ||
236 | Me | Me | EtSO2 | CH2CH2 | O-c-Pr | ||
237 | H | H | PrSO2 | CH2CH2 | O-c-Pr | ||
238 | H | Me | PrSO2 | CH2CH2 | O-c-Pr | ||
239 | Me | Me | PrSO2 | CH2CH2 | O-c-Pr | ||
240 | H | H | PhSO2 | CH2CH2 | O-c-Pr | ||
241 | H | Me | PhSO2 | CH2CH2 | O-c-Pr | ||
242 | Me | Me | PhSO2 | CH2CH2 | O-c-Pr | ||
243 | H | H | 4-Me-PhSO2 | CH2CH2 | O-c-Pr | ||
244 | H | Me | 4-Me-PhSO2 | CH2CH2 | O-c-Pr | ||
245 | Me | Me | 4-Me-PhSO2 | CH2CH2 | O-c-Pr | ||
246 | H | H | Bz | CH2CH2 | OCH2CF3 | ||
247 | H | Me | Bz | CH2CH2 | OCH2CF3 | ||
248 | Me | Me | Bz | CH2CH2 | OCH2CF3 | ||
249 | H | H | PhC(O)CH2 | CH2CH2 | OCH2CF3 | ||
250 | H | Me | PhC(O)CH2 | CH2CH2 | OCH2CF3 | ||
251 | Me | Me | PhC(O)CH2 | CH2CH2 | OCH2CF3 | ||
252 | H | H | 4-Me-Bz | CH2CH2 | OCH2CF3 | ||
253 | H | Me | 4-Me-Bz | CH2CH2 | OCH2CF3 | ||
254 | Me | Me | 4-Me-Bz | CH2CH2 | OCH2CF3 | ||
255 | H | H | MeSO2 | CH2CH2 | OCH2CF3 | ||
256 | H | Me | MeSO2 | CH2CH2 | OCH2CF3 | ||
257 | Me | Me | MeSO2 | CH2CH2 | OCH2CF3 | ||
258 | H | H | EtSO2 | CH2CH2 | OCH2CF3 | ||
259 | H | Me | EtSO2 | CH2CH2 | OCH2CF3 |
实施例编号 | R7a | R7b | R12 | L | R1 |
260 | Me | Me | EtSO2 | CH2CH2 | OCH2CF3 |
261 | H | H | PrSO2 | CH2CH2 | OCH2CF3 |
262 | H | Me | PrSO2 | CH2CH2 | OCH2CF3 |
263 | Me | Me | PrSO2 | CH2CH2 | OCH2CF3 |
264 | H | H | PhSO2 | CH2CH2 | OCH2CF3 |
265 | H | Me | PhSO2 | CH2CH2 | OCH2CF3 |
266 | Me | Me | PhSO2 | CH2CH2 | OCH2CF3 |
267 | H | H | 4-Me-PhSO2 | CH2CH2 | OCH2CF3 |
268 | H | Me | 4-Me-PhSO2 | CH2CH2 | OCH2CF3 |
269 | Me | Me | 4-Me-PhSO2 | CH2CH2 | OCH2CF3 |
270 | H | H | Bz | CH2CH2 | 0-环己基 |
271 | H | Me | Bz | CHMe | 0-环己基 |
272 | Me | Me | Bz | CHMe | 0-环己基 |
273 | H | H | PhC(O)CH2 | CHMe | 0-环己基 |
274 | H | Me | PhC(O)CH2 | CHMe | 0-环己基 |
275 | Me | Me | PhC(O)CH2 | CHMe | 0-环己基 |
276 | H | H | 4-Me-Bz | CHMe | 0-环己基 |
277 | H | Me | 4-Me-Bz | CHMe | 0-环己基 |
278 | Me | Me | 4-Me-Bz | CHMe | 0-环己基 |
279 | H | H | MeSO2 | CHMe | 0-环己基 |
280 | H | Me | MeSO2 | CHMe | 0-环己基 |
281 | Me | Me | MeSO2 | CHMe | 0-环己基 |
282 | H | H | EtSO2 | CHMe | 0-环己基 |
283 | H | Me | EtSO2 | CHMe | 0-环己基 |
284 | Me | Me | EtSO2 | CHMe | 0-环己基 |
285 | H | H | PrSO2 | CHMe | 0-环己基 |
286 | H | Me | PrSO2 | CHMe | 0-环己基 |
实施例编号 | R7a | R7b | R12 | L | R1 |
287 | Me | Me | PrSO2 | CHMe | 0-环己基 |
288 | H | H | PhSO2 | CHMe | 0-环己基 |
289 | H | Me | PhSO2 | CHMe | 0-环己基 |
290 | Me | Me | PhSO2 | CHMe | 0-环己基 |
291 | H | H | 4-Me-PhSO2 | CHMe | 0-环己基 |
292 | H | Me | 4-Me-PhSO2 | CHMe | 0-环己基 |
293 | Me | Me | 4-Me-PhSO2 | CHMe | 0-环己基 |
294 | H | H | Bz | CHMe | 0-环戊基 |
295 | H | Me | Bz | CHMe | 0-环戊基 |
296 | Me | Me | Bz | CHMe | 0-环戊基 |
297 | H | H | PhC(O)CH2 | CHMe | 0-环戊基 |
298 | H | Me | PhC(O)CH2 | CHMe | 0-环戊基 |
299 | Me | Me | PhC(O)CH2 | CHMe | 0-环戊基 |
300 | H | H | 4-Me-Bz | CHMe | 0-环戊基 |
301 | H | Me | 4-Me-Bz | CHMe | 0-环戊基 |
302 | Me | Me | 4-Me-Bz | CHMe | 0-环戊基 |
303 | H | H | MeSO2 | CHMe | 0-环戊基 |
304 | H | Me | MeSO2 | CHMe | 0-环戊基 |
305 | Me | Me | MeSO2 | CHMe | 0-环戊基 |
306 | H | H | EtSO2 | CHMe | 0-环戊基 |
307 | H | Me | EtSO2 | CHMe | 0-环戊基 |
308 | Me | Me | EtSO2 | CHMe | 0-环戊基 |
309 | H | H | PrSO2 | CHMe | 0-环戊基 |
310 | H | Me | PrSO2 | CHMe | 0-环戊基 |
311 | Me | Me | PrSO2 | CHMe | 0-环戊基 |
312 | H | H | PhSO2 | CHMe | 0-环戊基 |
313 | H | Me | PhSO2 | CHMe | 0-环戊基 |
实施例编号 | R7a | R7b | R12 | L | R1 |
314 | Me | Me | PhSO2 | CHMe | 0-环戊基 |
315 | H | H | 4-Me-PhSO2 | CHMe | 0-环戊基 |
316 | H | Me | 4-Me-PhSO2 | CHMe | 0-环戊基 |
317 | Me | Me | 4-Me-PhSO2 | CHMe | 0-环戊基 |
318 | H | H | Bz | CHMe | O-c-Bu |
319 | H | Me | Bz | CHMe | O-c-Bu |
320 | Me | Me | Bz | CHMe | O-c-Bu |
321 | H | H | PhC(O)CH2 | CHMe | O-c-Bu |
322 | H | Me | PhC(O)CH2 | CHMe | O-c-Bu |
323 | Me | Me | PhC(O)CH2 | CHMe | O-c-Bu |
324 | H | H | 4-Me-Bz | CHMe | O-c-Bu |
325 | H | Me | 4-Me-Bz | CHMe | O-c-Bu |
326 | Me | Me | 4-Me-Bz | CHMe | O-c-Bu |
327 | H | H | MeSO2 | CHMe | O-c-Bu |
328 | H | Me | MeSO2 | CHMe | O-c-Bu |
329 | Me | Me | MeSO2 | CHMe | O-c-Bu |
330 | H | H | EtSO2 | CHMe | O-c-Bu |
331 | H | Me | EtSO2 | CHMe | O-c-Bu |
332 | Me | Me | EtSO2 | CHMe | O-c-Bu |
333 | H | H | PrSO2 | CHMe | O-c-Bu |
334 | H | Me | PrSO2 | CHMe | O-c-Bu |
335 | Me | Me | PrSO2 | CHMe | O-c-Bu |
336 | H | H | PhSO2 | CHMe | O-c-Bu |
337 | H | Me | PhSO2 | CHMe | O-c-Bu |
338 | Me | Me | PhSO2 | CHMe | O-c-Bu |
339 | H | H | 4-Me-PhSO2 | CHMe | O-c-Bu |
340 | H | Me | 4-Me-PhSO2 | CHMe | O-c-Bu |
实施例编号 | R7a | R7b | R12 | L | R1 |
341 | Me | Me | 4-Me-PhSO2 | CHMe | O-c-Bu |
342 | H | H | Bz | CHMe | O-c-Pr |
343 | H | Me | Bz | CHMe | O-c-Pr |
344 | Me | Me | Bz | CHMe | O-c-Pr |
345 | H | H | PhC(O)CH2 | CHMe | O-c-Pr |
346 | H | Me | PhC(O)CH2 | CHMe | O-c-Pr |
347 | Me | Me | PhC(O)CH2 | CHMe | O-c-Pr |
348 | H | H | 4-Me-Bz | CHMe | O-c-Pr |
349 | H | Me | 4-Me-Bz | CHMe | O-c-Pr |
350 | Me | Me | 4-Me-Bz | CHMe | O-c-Pr |
351 | H | H | MeSO2 | CHMe | O-c-Pr |
352 | H | Me | MeSO2 | CHMe | O-c-Pr |
353 | Me | Me | MeSO2 | CHMe | O-c-Pr |
354 | H | H | EtSO2 | CHMe | O-c-Pr |
355 | H | Me | EtSO2 | CHMe | O-c-Pr |
356 | Me | Me | EtSO2 | CHMe | O-c-Pr |
357 | H | H | PrSO2 | CHMe | O-c-Pr |
358 | H | Me | PrSO2 | CHMe | O-c-Pr |
359 | Me | Me | PrSO2 | CHMe | O-c-Pr |
360 | H | H | PhSO2 | CHMe | O-c-Pr |
361 | H | Me | PhSO2 | CHMe | O-c-Pr |
362 | Me | Me | PhSO2 | CHMe | O-c-Pr |
363 | H | H | 4-Me-PhSO2 | CHMe | O-c-Pr |
364 | H | Me | 4-Me-PhSO2 | CHMe | O-c-Pr |
365 | Me | Me | 4-Me-PhSO2 | CHMe | O-c-Pr |
366 | H | H | Bz | CHMe | OCH2CF3 |
367 | H | Me | Bz | CHMe | OCH2CF3 |
实施例编号 | R7a | R7b | R12 | L | R1 |
368 | Me | Me | Bz | CHMe | OCH2CF3 |
369 | H | H | PhC(O)CH2 | CHMe | OCH2CF3 |
370 | H | Me | PhC(O)CH2 | CHMe | OCH2CF3 |
371 | Me | Me | PhC(O)CH2 | CHMe | OCH2CF3 |
372 | H | H | 4-Me-Bz | CHMe | OCH2CF3 |
373 | H | Me | 4-Me-Bz | CHMe | OCH2CF3 |
374 | Me | Me | 4-Me-Bz | CHMe | OCH2CF3 |
375 | H | H | MeSO2 | CHMe | OCH2CF3 |
376 | H | Me | MeSO2 | CHMe | OCH2CF3 |
377 | Me | Me | MeSO2 | CHMe | OCH2CF3 |
378 | H | H | EtSO2 | CHMe | OCH2CF3 |
379 | H | Me | EtSO2 | CHMe | OCH2CF3 |
380 | Me | Me | EtSO2 | CHMe | OCH2CF3 |
381 | H | H | PrSO2 | CHMe | OCH2CF3 |
382 | H | Me | PrsO2 | CHMe | OCH2CF3 |
383 | Me | Me | PrSO2 | CHMe | OCH2CF3 |
384 | H | H | PhSO2 | CHMe | OCH2CF3 |
385 | H | Me | PhSO2 | CHMe | OCH2CF3 |
386 | Me | Me | PhSO2 | CHMe | OCH2CF3 |
387 | H | H | 4-Me-PhSO2 | CHMe | OCH2CF3 |
388 | H | Me | 4-Me-PhSO2 | CHMe | OCH2CF3 |
389 | Me | Me | 4-Me-PhSO2 | CHMe | OCH2CF3 |
实施例编号 | L | R1 | 物性数据 |
390 | CH2 | OCH2CHF2 | 1H NMR(CDCl3):δ1.25(t,3H),2.05(m,2H),2.45(m,2H),2.85(m,2H),3.98(q,2H),3.95(m,2H),5.25(s,2H),5.9(m,1H),7.3(d,1H),8.15(d,1H),16.7(s,1H) |
391 | CH2 | OCH2CF3 | 1H NMR(CDCl3):δ1.3(t,3H),2.05(m,2H),2.45(m,2H),285(m,2H),3.38q,2H),4.0(q,2H),5.35(s,2H),7.32(d1H),8.08(d,1H),16.75(s,1H) |
392 | CH2 | OCH2CH2Cl | 1H NMR(CDCl3):δ1.3 (t,3H),2.05(m,2H),2.45(m,2H),2.85(m,2H),3.45(q,2H),3.65(t,2H),3.78(t,2H),5.35(s,2H),7.32(d,2H),8.1(d,1H),16.7(s,1H) |
393 | CH2 | SCH2CF3 | 1H NMR(CDCl3):δ1.3(t,3H),2.05(m,2H),2.45(m,2H),2.82(m,2H),3.35(m,2H),3.42(q,2H),4.62(s,2H),7.25(d,1H),8.05(d,1H),16.75(s,1H) |
394 | CH2 | OCH2CH2Br | |
395 | CH2 | OCH2CH2F | |
396 | CH2 | OCH2CF2CF2H | |
397 | CH2 | OCH2CF2CF3 | |
398 | CH2 | OCH2CF2CF2CF3 | |
399 | CH2CH2 | OCH2CH2Br | |
400 | CH2CH2 | OCH2CH2F |
实施例编号 | R1 | R2 | R3 |
436 | OCH2CF3 | Me | SO2Me |
437 | OCH2CF3 | Me | SO2Et |
438 | OCH2CF3 | SO2Me | Cl |
439 | OCH2CF3 | SO2Et | Cl |
440 | OCH2CF3 | SO2Me | CF3 |
441 | OCH2CF3 | SOMe | CF3 |
442 | OCH2CF3 | SMe | CF3 |
443 | OCH2CF3 | Cl | Cl |
444 | OCH2CF3 | Br | Br |
445 | OCH2CF2CF2H | Me | SO2Me |
446 | OCH2CF2CF2H | Me | SO2Et |
447 | OCH2CF2CF2H | SO2Me | Cl |
448 | OCH2CF2CF2H | SO2Et | Cl |
449 | OCH2CF2CF2H | SO2Me | CF3 |
450 | OCH2CF2CF2H | SOMe | CF3 |
451 | OCH2CF2CF2H | SMe | CF3 |
实施例编号 | R1 | R2 | R3 |
499 | OCH2CH2F | Me | SO2Me |
500 | OCH2CH2F | Me | SO2Et |
501 | OCH2CH2F | SO2Me | Cl |
502 | OCH2CH2F | SO2Et | Cl |
503 | OCH2CH2F | SO2Me | CF3 |
504 | OCH2CH2F | SOMe | CF3 |
505 | OCH2CH2F | SMe | CF3 |
506 | OCH2CH2F | Cl | Cl |
507 | OCH2CH2F | Br | Br |
508 | OCH2CH2Br | Me | SO2Me |
509 | OCH2CH2Br | Me | SO2Et |
510 | OCH2CH2Br | SO2Me | Cl |
511 | OCH2CH2Br | SO2Et | Cl |
512 | OCH2CH2Br | SO2Me | CF3 |
513 | OCH2CH2Br | SOMe | CF3 |
514 | OCH2CH2Br | SMe | CF3 |
515 | OCH2CH2Br | Cl | Cl |
516 | OCH2CH2Br | Br | Br |
Claims (13)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE19846792.3 | 1998-10-10 | ||
DE19846792A DE19846792A1 (de) | 1998-10-10 | 1998-10-10 | Benzoylcyclohexandione, Verfahren zur ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
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CN1323292A true CN1323292A (zh) | 2001-11-21 |
CN1269800C CN1269800C (zh) | 2006-08-16 |
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DE (2) | DE19846792A1 (zh) |
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Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4783213A (en) * | 1986-10-16 | 1988-11-08 | Stauffer Chemical Company | Certain 2-(2-substituted benzoyl)-4-(substituted oxy or substituted thio)-1,3-cyclohexanediones |
US4838932A (en) * | 1987-08-20 | 1989-06-13 | Stauffer Chemical Company | Certain 2-(2-substituted benzoyl)-4-(substituted imino, oximino or carbonyl)-1,3-cyclohexanediones |
JP2739738B2 (ja) * | 1987-10-19 | 1998-04-15 | 日産化学工業株式会社 | 置換ベンゾイル誘導体および選択性除草剤 |
US4957538A (en) * | 1988-11-18 | 1990-09-18 | Ici Americas Inc. | Certain 2-(2',3',4'-trisubstituted benzoyl)-1,3-cyclohexanediones |
EP0502492A3 (en) * | 1991-03-06 | 1992-11-25 | Hoechst Aktiengesellschaft | Haloalkoxy-substituted benzoylcyclohexanediones as herbicides and plant growth regulators |
DE4241999A1 (de) * | 1992-12-12 | 1994-06-16 | Hoechst Ag | Benzoylcyclohexenone, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
JPH07206808A (ja) * | 1994-01-17 | 1995-08-08 | Hokko Chem Ind Co Ltd | シクロヘキサンジオン誘導体および除草剤 |
JPH0820544A (ja) | 1994-07-04 | 1996-01-23 | Takasago Internatl Corp | 活性酸素消去剤ならびにこれを配合した食品および化粧料 |
JPH0820554A (ja) * | 1994-07-04 | 1996-01-23 | Hokko Chem Ind Co Ltd | シクロヘキサンジオン誘導体および除草剤 |
US6165944A (en) * | 1997-01-17 | 2000-12-26 | Basf Aktiengesellschaft | 4-(3-heterocyclyl-1-benzoyl) pyrazoles and their use as herbicides |
JPH1121274A (ja) * | 1997-07-01 | 1999-01-26 | Nippon Soda Co Ltd | ベンゾイルシクロヘキサンジオン誘導体および除草剤 |
GB2327418A (en) | 1997-07-18 | 1999-01-27 | Rhone Poulenc Agriculture | Derivatives of 2-benzoylcyclohexane-1,3-dione |
DE59814019D1 (de) | 1997-08-07 | 2007-07-12 | Basf Ag | 2-benzoyl-cyclohexan-1,3-dione |
AU9068498A (en) * | 1997-08-07 | 1999-03-16 | Basf Aktiengesellschaft | 2-benzoyl-cyclohexane-1,3-dione as herbicides |
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1998
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1999
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