KR890000481B1 - 제초제용 2,6-비스-플루오로메틸-디하이드로피리딘-3,5-디카르복실릭에시드 에스테르의 제조방법 - Google Patents
제초제용 2,6-비스-플루오로메틸-디하이드로피리딘-3,5-디카르복실릭에시드 에스테르의 제조방법 Download PDFInfo
- Publication number
- KR890000481B1 KR890000481B1 KR1019840004808D KR8404808D KR890000481B1 KR 890000481 B1 KR890000481 B1 KR 890000481B1 KR 1019840004808 D KR1019840004808 D KR 1019840004808D KR 8404808 D KR8404808 D KR 8404808D KR 890000481 B1 KR890000481 B1 KR 890000481B1
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- alkyl
- trifluoromethyl
- radical
- bis
- Prior art date
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 32
- 230000002363 herbicidal effect Effects 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 66
- -1 alkyl radicals Chemical class 0.000 claims description 53
- 239000011541 reaction mixture Substances 0.000 claims description 43
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 34
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
- 150000001299 aldehydes Chemical class 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical group CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 10
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 9
- OCJKUQIPRNZDTK-UHFFFAOYSA-N ethyl 4,4,4-trifluoro-3-oxobutanoate Chemical group CCOC(=O)CC(=O)C(F)(F)F OCJKUQIPRNZDTK-UHFFFAOYSA-N 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 239000012024 dehydrating agents Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 7
- NBVXSUQYWXRMNV-UHFFFAOYSA-N monofluoromethane Natural products FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 7
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical group CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- ZRNSSRODJSSVEJ-UHFFFAOYSA-N 2-methylpentacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(C)C ZRNSSRODJSSVEJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 125000005197 alkyl carbonyloxy alkyl group Chemical group 0.000 claims description 4
- 239000000908 ammonium hydroxide Substances 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- LKMUBWWZTSZGGV-UHFFFAOYSA-N methyl 4,4,4-trifluoro-3-oxobutanoate Chemical compound COC(=O)CC(=O)C(F)(F)F LKMUBWWZTSZGGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 3
- CBDPWKVOPADMJC-UHFFFAOYSA-N ethyl 4,4-difluoro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)C(F)F CBDPWKVOPADMJC-UHFFFAOYSA-N 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 3
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 3
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims 2
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims 2
- HLVMZRXHDRXSJY-UHFFFAOYSA-N [CH2]SC Chemical group [CH2]SC HLVMZRXHDRXSJY-UHFFFAOYSA-N 0.000 claims 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 83
- 239000000203 mixture Substances 0.000 description 82
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 72
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- 238000002360 preparation method Methods 0.000 description 49
- 239000000047 product Substances 0.000 description 46
- 239000003921 oil Substances 0.000 description 43
- 235000019198 oils Nutrition 0.000 description 43
- TUDHHJQPQZFEIH-UHFFFAOYSA-N piperidine-4,4-diol Chemical compound OC1(O)CCNCC1 TUDHHJQPQZFEIH-UHFFFAOYSA-N 0.000 description 41
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 35
- 238000000921 elemental analysis Methods 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 27
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 26
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 239000004480 active ingredient Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 239000007787 solid Substances 0.000 description 19
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- 238000002844 melting Methods 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 16
- 239000000460 chlorine Substances 0.000 description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- 239000003480 eluent Substances 0.000 description 14
- 239000012043 crude product Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 11
- 229910021529 ammonia Inorganic materials 0.000 description 11
- 239000004009 herbicide Substances 0.000 description 11
- 239000005457 ice water Substances 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- 241000196324 Embryophyta Species 0.000 description 10
- 239000003623 enhancer Substances 0.000 description 10
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 10
- 239000000463 material Substances 0.000 description 9
- 239000003208 petroleum Substances 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000002689 soil Substances 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- MMWRGWQTAMNAFC-UHFFFAOYSA-N 1,2-dihydropyridine Chemical compound C1NC=CC=C1 MMWRGWQTAMNAFC-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 description 7
- 239000012259 ether extract Substances 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 238000000023 Kugelrohr distillation Methods 0.000 description 6
- 235000011114 ammonium hydroxide Nutrition 0.000 description 6
- WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 6
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 150000003222 pyridines Chemical class 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 235000013877 carbamide Nutrition 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 235000008504 concentrate Nutrition 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 239000000080 wetting agent Substances 0.000 description 5
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- RDOAUPPSCNSYPM-UHFFFAOYSA-N 3,4-dihydropyridine Chemical class C1CC=NC=C1 RDOAUPPSCNSYPM-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000014509 gene expression Effects 0.000 description 3
- 230000035784 germination Effects 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 241001148727 Bromus tectorum Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 244000067505 Xanthium strumarium Species 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000003931 anilides Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- CZYYZLCVCGMUQH-UHFFFAOYSA-N diethyl 2,6-dihydroxy-4-propan-2-yl-2,6-bis(trifluoromethyl)piperidine-3,5-dicarboxylate Chemical compound CCOC(=O)C1C(C(C)C)C(C(=O)OCC)C(O)(C(F)(F)F)NC1(O)C(F)(F)F CZYYZLCVCGMUQH-UHFFFAOYSA-N 0.000 description 2
- AHPKRIKCUUDCAN-UHFFFAOYSA-N diethyl 4-(acetyloxymethyl)-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC(C(F)(F)F)=C(C(=O)OCC)C1COC(C)=O AHPKRIKCUUDCAN-UHFFFAOYSA-N 0.000 description 2
- JWSNWHPBQOECBT-UHFFFAOYSA-N diethyl 4-(phenylmethoxymethyl)-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC(C(F)(F)F)=C(C(=O)OCC)C1COCC1=CC=CC=C1 JWSNWHPBQOECBT-UHFFFAOYSA-N 0.000 description 2
- PCKIXHBSEWBXDI-UHFFFAOYSA-N diethyl 4-cyclohexyl-2,6-bis(difluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)F)NC(C(F)F)=C(C(=O)OCC)C1C1CCCCC1 PCKIXHBSEWBXDI-UHFFFAOYSA-N 0.000 description 2
- CSEWMUDHDDARLJ-UHFFFAOYSA-N diethyl 4-cyclohexyl-2-(difluoromethyl)-6-(trifluoromethyl)pyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)F)N=C(C(F)(F)F)C(C(=O)OCC)=C1C1CCCCC1 CSEWMUDHDDARLJ-UHFFFAOYSA-N 0.000 description 2
- WQIKIFYMKDAWBQ-UHFFFAOYSA-N diethyl 4-propan-2-yl-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC(C(F)(F)F)=C(C(=O)OCC)C1C(C)C WQIKIFYMKDAWBQ-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- RZTAMFZIAATZDJ-UHFFFAOYSA-N felodipine Chemical group CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC(Cl)=C1Cl RZTAMFZIAATZDJ-UHFFFAOYSA-N 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 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 2
- 229920005610 lignin Polymers 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- GJAWHXHKYYXBSV-UHFFFAOYSA-L quinolinate(2-) Chemical compound [O-]C(=O)C1=CC=CN=C1C([O-])=O GJAWHXHKYYXBSV-UHFFFAOYSA-L 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- 150000003527 tetrahydropyrans Chemical class 0.000 description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
- 239000010455 vermiculite Substances 0.000 description 2
- 229910052902 vermiculite Inorganic materials 0.000 description 2
- 235000019354 vermiculite Nutrition 0.000 description 2
- LOGOUZJNILIJFF-UHFFFAOYSA-N (5-chloro-2-methylphenyl)urea Chemical compound CC1=CC=C(Cl)C=C1NC(N)=O LOGOUZJNILIJFF-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- NCNSBFDGXBKAKB-UHFFFAOYSA-N (methylsulfanyl)acetaldehyde Chemical compound CSCC=O NCNSBFDGXBKAKB-UHFFFAOYSA-N 0.000 description 1
- VCLSSIUDTNSANT-UHFFFAOYSA-N 1,4-dihydropyridine-3,5-dicarbonitrile Chemical compound N#CC1=CNC=C(C#N)C1 VCLSSIUDTNSANT-UHFFFAOYSA-N 0.000 description 1
- 238000004293 19F NMR spectroscopy Methods 0.000 description 1
- NDUPDOJHUQKPAG-UHFFFAOYSA-M 2,2-Dichloropropanoate Chemical compound CC(Cl)(Cl)C([O-])=O NDUPDOJHUQKPAG-UHFFFAOYSA-M 0.000 description 1
- VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 description 1
- AHHYEFQWMUXGFH-UHFFFAOYSA-N 2,3-dihydroxypiperidine-1,2-dicarboxylic acid Chemical compound OC1CCCN(C(O)=O)C1(O)C(O)=O AHHYEFQWMUXGFH-UHFFFAOYSA-N 0.000 description 1
- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-DOMIDYPGSA-N 2-(2,4-dichlorophenoxy)acetic acid Chemical compound OC(=O)[14CH2]OC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-DOMIDYPGSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 1
- OWZPCEFYPSAJFR-UHFFFAOYSA-N 2-(butan-2-yl)-4,6-dinitrophenol Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O OWZPCEFYPSAJFR-UHFFFAOYSA-N 0.000 description 1
- ATMQIVZKYBCIGA-UHFFFAOYSA-N 2-chloro-n-(2-ethyl-6-methylphenyl)-n-(2-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(=O)CCl)C(C)(C)OC ATMQIVZKYBCIGA-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- LTNUSYNQZJZUSY-UHFFFAOYSA-N 3,3-dimethylbutanal Chemical compound CC(C)(C)CC=O LTNUSYNQZJZUSY-UHFFFAOYSA-N 0.000 description 1
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 1
- XXWKBLJJTQQHJD-UHFFFAOYSA-N 3-(trifluoromethoxycarbonyl)-3,4-dihydropyridine-5-carboxylic acid Chemical compound C1C(C=NC=C1C(=O)O)C(=O)OC(F)(F)F XXWKBLJJTQQHJD-UHFFFAOYSA-N 0.000 description 1
- LUSRTGSMUARNAX-UHFFFAOYSA-N 3-O-ethyl 5-O-methyl 2-ethyl-4-(2-methylpropyl)-6-(trifluoromethyl)-1,2-dihydropyridine-3,5-dicarboxylate Chemical compound C(C)C1NC(=C(C(=C1C(=O)OCC)CC(C)C)C(=O)OC)C(F)(F)F LUSRTGSMUARNAX-UHFFFAOYSA-N 0.000 description 1
- NMRJOYVVUJVJKX-UHFFFAOYSA-N 3-O-ethyl 5-O-methyl 4-methyl-2-propan-2-yl-6-(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CC1C(=C(NC(=C1C(=O)OC)C(F)(F)F)C(C)C)C(=O)OCC NMRJOYVVUJVJKX-UHFFFAOYSA-N 0.000 description 1
- LIQBKSIZAXKCPA-UHFFFAOYSA-N 4,4,4-trifluoro-3-oxobutanoic acid Chemical compound OC(=O)CC(=O)C(F)(F)F LIQBKSIZAXKCPA-UHFFFAOYSA-N 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- 240000000321 Abutilon grandifolium Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- MDBGGTQNNUOQRC-UHFFFAOYSA-N Allidochlor Chemical compound ClCC(=O)N(CC=C)CC=C MDBGGTQNNUOQRC-UHFFFAOYSA-N 0.000 description 1
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- MYPXRIPQWPEDPN-UHFFFAOYSA-N C(C(C)C)C1=C(C(NC(=C1C(=O)OCC)C(F)(F)F)C(F)(F)F)C(=O)OCC Chemical compound C(C(C)C)C1=C(C(NC(=C1C(=O)OCC)C(F)(F)F)C(F)(F)F)C(=O)OCC MYPXRIPQWPEDPN-UHFFFAOYSA-N 0.000 description 1
- CECPZKUMGXGAJO-UHFFFAOYSA-N C1=CC=C(C=C1)COCC2C(C(NC(C2C(=O)O)(C(F)(F)F)O)(C(F)(F)F)O)C(=O)O Chemical compound C1=CC=C(C=C1)COCC2C(C(NC(C2C(=O)O)(C(F)(F)F)O)(C(F)(F)F)O)C(=O)O CECPZKUMGXGAJO-UHFFFAOYSA-N 0.000 description 1
- IYRXWPKXPKXLJJ-UHFFFAOYSA-N CCC1C(C(NC(C1C(=O)OCC)(CC(F)(F)F)O)(CC(F)(F)F)O)C(=O)OCC Chemical compound CCC1C(C(NC(C1C(=O)OCC)(CC(F)(F)F)O)(CC(F)(F)F)O)C(=O)OCC IYRXWPKXPKXLJJ-UHFFFAOYSA-N 0.000 description 1
- RKECAJFMHWHHBI-UHFFFAOYSA-N CCCC1=C[S+](CCC)C(NC([O-])=O)=C1CCC Chemical compound CCCC1=C[S+](CCC)C(NC([O-])=O)=C1CCC RKECAJFMHWHHBI-UHFFFAOYSA-N 0.000 description 1
- PDHKPXNPYQXILD-UHFFFAOYSA-K C[As]([O-])(=O)[O-].[Na+].[Na+].C[As](O)(=O)[O-].[Na+] Chemical compound C[As]([O-])(=O)[O-].[Na+].[Na+].C[As](O)(=O)[O-].[Na+] PDHKPXNPYQXILD-UHFFFAOYSA-K 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- HSSBORCLYSCBJR-UHFFFAOYSA-N Chloramben Chemical compound NC1=CC(Cl)=CC(C(O)=O)=C1Cl HSSBORCLYSCBJR-UHFFFAOYSA-N 0.000 description 1
- 241000132536 Cirsium Species 0.000 description 1
- 235000005853 Cyperus esculentus Nutrition 0.000 description 1
- 240000001505 Cyperus odoratus Species 0.000 description 1
- SPANOECCGNXGNR-UITAMQMPSA-N Diallat Chemical compound CC(C)N(C(C)C)C(=O)SC\C(Cl)=C\Cl SPANOECCGNXGNR-UITAMQMPSA-N 0.000 description 1
- GUVLYNGULCJVDO-UHFFFAOYSA-N EPTC Chemical compound CCCN(CCC)C(=O)SCC GUVLYNGULCJVDO-UHFFFAOYSA-N 0.000 description 1
- 244000248416 Fagopyrum cymosum Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 240000001549 Ipomoea eriocarpa Species 0.000 description 1
- 235000005146 Ipomoea eriocarpa Nutrition 0.000 description 1
- PSYBGEADHLUXCS-UHFFFAOYSA-N Isocil Chemical compound CC(C)N1C(=O)NC(C)=C(Br)C1=O PSYBGEADHLUXCS-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 235000003403 Limnocharis flava Nutrition 0.000 description 1
- 239000005574 MCPA Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- OKIBNKKYNPBDRS-UHFFFAOYSA-N Mefluidide Chemical compound CC(=O)NC1=CC(NS(=O)(=O)C(F)(F)F)=C(C)C=C1C OKIBNKKYNPBDRS-UHFFFAOYSA-N 0.000 description 1
- 235000012629 Mentha aquatica Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CCGPUGMWYLICGL-UHFFFAOYSA-N Neburon Chemical compound CCCCN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 CCGPUGMWYLICGL-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 241000209117 Panicum Species 0.000 description 1
- 235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 1
- 235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 1
- 240000000275 Persicaria hydropiper Species 0.000 description 1
- 235000017337 Persicaria hydropiper Nutrition 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 1
- 235000004442 Polygonum persicaria Nutrition 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 241000533293 Sesbania emerus Species 0.000 description 1
- 240000002439 Sorghum halepense Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- XJCLWVXTCRQIDI-UHFFFAOYSA-N Sulfallate Chemical compound CCN(CC)C(=S)SCC(Cl)=C XJCLWVXTCRQIDI-UHFFFAOYSA-N 0.000 description 1
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 1
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 150000003869 acetamides Chemical class 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 150000008061 acetanilides Chemical class 0.000 description 1
- XBMGHVJWJAIHKS-UHFFFAOYSA-N acetic acid ethyl 2,2,2-trifluoroacetate Chemical compound C(C)(=O)O.FC(C(=O)OCC)(F)F XBMGHVJWJAIHKS-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000005002 aryl methyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- ZCILODAAHLISPY-UHFFFAOYSA-N biphenyl ether Natural products C1=C(CC=C)C(O)=CC(OC=2C(=CC(CC=C)=CC=2)O)=C1 ZCILODAAHLISPY-UHFFFAOYSA-N 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- YYRMJZQKEFZXMX-UHFFFAOYSA-N calcium;phosphoric acid Chemical compound [Ca+2].OP(O)(O)=O.OP(O)(O)=O YYRMJZQKEFZXMX-UHFFFAOYSA-N 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- QZXCCPZJCKEPSA-UHFFFAOYSA-N chlorfenac Chemical compound OC(=O)CC1=C(Cl)C=CC(Cl)=C1Cl QZXCCPZJCKEPSA-UHFFFAOYSA-N 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 1
- CWJSHJJYOPWUGX-UHFFFAOYSA-N chlorpropham Chemical compound CC(C)OC(=O)NC1=CC=CC(Cl)=C1 CWJSHJJYOPWUGX-UHFFFAOYSA-N 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- ABULZPRYJJYANG-UHFFFAOYSA-N cyclohexane;methyl acetate Chemical compound COC(C)=O.C1CCCCC1 ABULZPRYJJYANG-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000005796 dehydrofluorination reaction Methods 0.000 description 1
- 238000001784 detoxification Methods 0.000 description 1
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 1
- 125000006003 dichloroethyl group Chemical group 0.000 description 1
- 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- ZVYJMNYGRIDYKI-UHFFFAOYSA-N diethyl 2,6-bis(difluoromethyl)-4-propyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCCC1C(C(=O)OCC)=C(C(F)F)NC(C(F)F)=C1C(=O)OCC ZVYJMNYGRIDYKI-UHFFFAOYSA-N 0.000 description 1
- ZXAWHLVKRUWHRY-UHFFFAOYSA-N diethyl 2,6-dihydroxy-4-(2-methylpropyl)-2,6-bis(trifluoromethyl)piperidine-3,5-dicarboxylate Chemical compound CCOC(=O)C1C(CC(C)C)C(C(=O)OCC)C(O)(C(F)(F)F)NC1(O)C(F)(F)F ZXAWHLVKRUWHRY-UHFFFAOYSA-N 0.000 description 1
- DAYXOPHTLAIXNI-UHFFFAOYSA-N diethyl 2,6-dihydroxy-4-methyl-2,6-bis(trifluoromethyl)piperidine-3,5-dicarboxylate Chemical compound CCOC(=O)C1C(C)C(C(=O)OCC)C(O)(C(F)(F)F)NC1(O)C(F)(F)F DAYXOPHTLAIXNI-UHFFFAOYSA-N 0.000 description 1
- UALBMALJKYZROX-UHFFFAOYSA-N diethyl 2,6-dihydroxy-4-phenyl-2,6-bis(trifluoromethyl)piperidine-3,5-dicarboxylate Chemical compound CCOC(=O)C1C(O)(C(F)(F)F)NC(C(F)(F)F)(O)C(C(=O)OCC)C1C1=CC=CC=C1 UALBMALJKYZROX-UHFFFAOYSA-N 0.000 description 1
- OLVIWZURBFUPJK-UHFFFAOYSA-N diethyl 2,6-dihydroxy-4-propyl-2,6-bis(trifluoromethyl)piperidine-3,5-dicarboxylate Chemical compound CCCC1C(C(=O)OCC)C(O)(C(F)(F)F)NC(O)(C(F)(F)F)C1C(=O)OCC OLVIWZURBFUPJK-UHFFFAOYSA-N 0.000 description 1
- FNOWBFBMMDXGRX-UHFFFAOYSA-N diethyl 2,6-dihydroxy-4-pyridin-4-yl-2,6-bis(trifluoromethyl)piperidine-3,5-dicarboxylate Chemical compound CCOC(=O)C1C(O)(C(F)(F)F)NC(C(F)(F)F)(O)C(C(=O)OCC)C1C1=CC=NC=C1 FNOWBFBMMDXGRX-UHFFFAOYSA-N 0.000 description 1
- UXIKETQSQUSCFK-UHFFFAOYSA-N diethyl 2-(difluoromethyl)-4-propyl-6-(trifluoromethyl)pyridine-3,5-dicarboxylate Chemical compound CCCC1=C(C(=O)OCC)C(C(F)F)=NC(C(F)(F)F)=C1C(=O)OCC UXIKETQSQUSCFK-UHFFFAOYSA-N 0.000 description 1
- BAGRCZJSEZFXCL-UHFFFAOYSA-N diethyl 4-(2,2-dimethylpropyl)-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC(C(F)(F)F)=C(C(=O)OCC)C1CC(C)(C)C BAGRCZJSEZFXCL-UHFFFAOYSA-N 0.000 description 1
- JLFKCBKBSQKHAF-UHFFFAOYSA-N diethyl 4-(2-methylpropyl)-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC(C(F)(F)F)=C(C(=O)OCC)C1CC(C)C JLFKCBKBSQKHAF-UHFFFAOYSA-N 0.000 description 1
- UYIDEVKPTRZDEE-UHFFFAOYSA-N diethyl 4-(2-methylpropyl)-2,6-bis(trifluoromethyl)pyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(CC(C)C)C(C(=O)OCC)=C(C(F)(F)F)N=C1C(F)(F)F UYIDEVKPTRZDEE-UHFFFAOYSA-N 0.000 description 1
- SULMYDAFNFRSPU-UHFFFAOYSA-N diethyl 4-(chloromethyl)-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC(C(F)(F)F)=C(C(=O)OCC)C1CCl SULMYDAFNFRSPU-UHFFFAOYSA-N 0.000 description 1
- LCAPVZPVUYNAKH-UHFFFAOYSA-N diethyl 4-(furan-2-yl)-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC(C(F)(F)F)=C(C(=O)OCC)C1C1=CC=CO1 LCAPVZPVUYNAKH-UHFFFAOYSA-N 0.000 description 1
- KXBVHDQIORQKDX-UHFFFAOYSA-N diethyl 4-(hydroxymethyl)-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC(C(F)(F)F)=C(C(=O)OCC)C1CO KXBVHDQIORQKDX-UHFFFAOYSA-N 0.000 description 1
- CNHBXFCYMDBXDB-UHFFFAOYSA-N diethyl 4-(methylsulfanylmethyl)-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC(C(F)(F)F)=C(C(=O)OCC)C1CSC CNHBXFCYMDBXDB-UHFFFAOYSA-N 0.000 description 1
- IYDJVFUHPPOVRY-UHFFFAOYSA-N diethyl 4-benzyl-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC(C(F)(F)F)=C(C(=O)OCC)C1CC1=CC=CC=C1 IYDJVFUHPPOVRY-UHFFFAOYSA-N 0.000 description 1
- SVLBXAGSIPOWNS-UHFFFAOYSA-N diethyl 4-benzyl-2,6-dihydroxy-2,6-bis(trifluoromethyl)piperidine-3,5-dicarboxylate Chemical compound CCOC(=O)C1C(O)(C(F)(F)F)NC(C(F)(F)F)(O)C(C(=O)OCC)C1CC1=CC=CC=C1 SVLBXAGSIPOWNS-UHFFFAOYSA-N 0.000 description 1
- ILEVABWRDFHBOI-UHFFFAOYSA-N diethyl 4-butan-2-yl-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(NC(=C(C1C(C)CC)C(=O)OCC)C(F)(F)F)C(F)(F)F ILEVABWRDFHBOI-UHFFFAOYSA-N 0.000 description 1
- TYRVPNSAQVAPHA-UHFFFAOYSA-N diethyl 4-butyl-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCCCC1C(C(=O)OCC)=C(C(F)(F)F)NC(C(F)(F)F)=C1C(=O)OCC TYRVPNSAQVAPHA-UHFFFAOYSA-N 0.000 description 1
- VKQCVRVWEGGMOG-UHFFFAOYSA-N diethyl 4-butyl-2,6-dihydroxy-2,6-bis(trifluoromethyl)piperidine-3,5-dicarboxylate Chemical compound CCCCC1C(C(=O)OCC)C(O)(C(F)(F)F)NC(O)(C(F)(F)F)C1C(=O)OCC VKQCVRVWEGGMOG-UHFFFAOYSA-N 0.000 description 1
- NHVHQWRNMTYRHG-UHFFFAOYSA-N diethyl 4-ethyl-1,4-dihydroxy-2,6-bis(trifluoromethyl)piperidine-3,5-dicarboxylate Chemical compound CCOC(=O)C1C(C(F)(F)F)N(O)C(C(F)(F)F)C(C(=O)OCC)C1(O)CC NHVHQWRNMTYRHG-UHFFFAOYSA-N 0.000 description 1
- LZYYOEITHIIOIO-UHFFFAOYSA-N diethyl 4-ethyl-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC(C(F)(F)F)=C(C(=O)OCC)C1CC LZYYOEITHIIOIO-UHFFFAOYSA-N 0.000 description 1
- ULRRJVGKMSKJCN-UHFFFAOYSA-N diethyl 4-ethyl-2,6-bis(trifluoromethyl)-3,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1C(CC)C(C(=O)OCC)=C(C(F)(F)F)N=C1C(F)(F)F ULRRJVGKMSKJCN-UHFFFAOYSA-N 0.000 description 1
- GCHZJYILSPLAGV-UHFFFAOYSA-N diethyl 4-ethyl-2,6-dihydroxy-2,6-bis(trifluoromethyl)piperidine-3,5-dicarboxylate Chemical compound CCOC(=O)C1C(CC)C(C(=O)OCC)C(O)(C(F)(F)F)NC1(O)C(F)(F)F GCHZJYILSPLAGV-UHFFFAOYSA-N 0.000 description 1
- SVZGVEJQQBGUEJ-UHFFFAOYSA-N diethyl 4-methyl-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC(C(F)(F)F)=C(C(=O)OCC)C1C SVZGVEJQQBGUEJ-UHFFFAOYSA-N 0.000 description 1
- YXFLRUNKYAFMMK-UHFFFAOYSA-N diethyl 4-phenyl-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC(C(F)(F)F)=C(C(=O)OCC)C1C1=CC=CC=C1 YXFLRUNKYAFMMK-UHFFFAOYSA-N 0.000 description 1
- QWQNEQHPTRNLPP-UHFFFAOYSA-N diethyl 4-propyl-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCCC1C(C(=O)OCC)=C(C(F)(F)F)NC(C(F)(F)F)=C1C(=O)OCC QWQNEQHPTRNLPP-UHFFFAOYSA-N 0.000 description 1
- FQALQSNVGLOOBM-UHFFFAOYSA-N diethyl 4-pyridin-4-yl-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC(C(F)(F)F)=C(C(=O)OCC)C1C1=CC=NC=C1 FQALQSNVGLOOBM-UHFFFAOYSA-N 0.000 description 1
- IAGQAFFFTYNLFV-UHFFFAOYSA-N diethyl 4-thiophen-2-yl-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC(C(F)(F)F)=C(C(=O)OCC)C1C1=CC=CS1 IAGQAFFFTYNLFV-UHFFFAOYSA-N 0.000 description 1
- 125000006001 difluoroethyl group Chemical group 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- SPCNPOWOBZQWJK-UHFFFAOYSA-N dimethoxy-(2-propan-2-ylsulfanylethylsulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical compound COP(=S)(OC)SCCSC(C)C SPCNPOWOBZQWJK-UHFFFAOYSA-N 0.000 description 1
- ICHAHAFIMBUDKO-UHFFFAOYSA-N dimethyl 2-(difluoromethyl)-4-(2-methylpropyl)-6-(trifluoromethyl)-1,2-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(CC(C)C)C(C(=O)OC)=C(C(F)(F)F)NC1C(F)F ICHAHAFIMBUDKO-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- ZRLNPHNIOXIZHR-UHFFFAOYSA-N ethyl 3-aminopent-2-enoate Chemical compound CCOC(=O)C=C(N)CC ZRLNPHNIOXIZHR-UHFFFAOYSA-N 0.000 description 1
- KQBYNGJTZNCQCO-UHFFFAOYSA-N ethyl 4-fluoro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)CF KQBYNGJTZNCQCO-UHFFFAOYSA-N 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003864 humus Substances 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052900 illite Inorganic materials 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- XCOBTUNSZUJCDH-UHFFFAOYSA-B lithium magnesium sodium silicate Chemical compound [Li+].[Li+].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Na+].[Na+].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3 XCOBTUNSZUJCDH-UHFFFAOYSA-B 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- BMLIZLVNXIYGCK-UHFFFAOYSA-N monuron Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C=C1 BMLIZLVNXIYGCK-UHFFFAOYSA-N 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- WMIPWRSVIZFVQB-UHFFFAOYSA-N n,n-dimethyl-2,2-diphenylacetamide Chemical compound C=1C=CC=CC=1C(C(=O)N(C)C)C1=CC=CC=C1.C=1C=CC=CC=1C(C(=O)N(C)C)C1=CC=CC=C1 WMIPWRSVIZFVQB-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- XITQUSLLOSKDTB-UHFFFAOYSA-N nitrofen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C=C1Cl XITQUSLLOSKDTB-UHFFFAOYSA-N 0.000 description 1
- VGIBGUSAECPPNB-UHFFFAOYSA-L nonaaluminum;magnesium;tripotassium;1,3-dioxido-2,4,5-trioxa-1,3-disilabicyclo[1.1.1]pentane;iron(2+);oxygen(2-);fluoride;hydroxide Chemical compound [OH-].[O-2].[O-2].[O-2].[O-2].[O-2].[F-].[Mg+2].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[K+].[K+].[K+].[Fe+2].O1[Si]2([O-])O[Si]1([O-])O2.O1[Si]2([O-])O[Si]1([O-])O2.O1[Si]2([O-])O[Si]1([O-])O2.O1[Si]2([O-])O[Si]1([O-])O2.O1[Si]2([O-])O[Si]1([O-])O2.O1[Si]2([O-])O[Si]1([O-])O2.O1[Si]2([O-])O[Si]1([O-])O2 VGIBGUSAECPPNB-UHFFFAOYSA-L 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 235000008935 nutritious Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- INFDPOAKFNIJBF-UHFFFAOYSA-N paraquat Chemical compound C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 INFDPOAKFNIJBF-UHFFFAOYSA-N 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000005359 phenoxyalkyl group Chemical group 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- YWWGOKNLNRUDAC-UHFFFAOYSA-N piperidine-3,5-dicarboxylic acid Chemical compound OC(=O)C1CNCC(C(O)=O)C1 YWWGOKNLNRUDAC-UHFFFAOYSA-N 0.000 description 1
- 150000003053 piperidines Chemical group 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
- WJNRPILHGGKWCK-UHFFFAOYSA-N propazine Chemical compound CC(C)NC1=NC(Cl)=NC(NC(C)C)=N1 WJNRPILHGGKWCK-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
- GGOZGYRTNQBSSA-UHFFFAOYSA-N pyridine-2,3-diol Chemical compound OC1=CC=CN=C1O GGOZGYRTNQBSSA-UHFFFAOYSA-N 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- RVULBHWZFCBODE-UHFFFAOYSA-M sodium;5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical compound [Na+].C1=C([N+]([O-])=O)C(C(=O)[O-])=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 RVULBHWZFCBODE-UHFFFAOYSA-M 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound 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
- 150000003672 ureas Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 238000002424 x-ray crystallography Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
-
- 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
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Cephalosporin Compounds (AREA)
- Particle Accelerators (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Confectionery (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US522281 | 1983-08-10 | ||
| US52228183A | 1983-08-11 | 1983-08-11 | |
| US60202284A | 1984-04-24 | 1984-04-24 | |
| US602022 | 1984-04-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR890000481B1 true KR890000481B1 (ko) | 1989-03-18 |
Family
ID=27060765
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840004808D Expired KR890000481B1 (ko) | 1983-08-10 | 1984-08-10 | 제초제용 2,6-비스-플루오로메틸-디하이드로피리딘-3,5-디카르복실릭에시드 에스테르의 제조방법 |
| KR8404808A Expired KR870001233B1 (en) | 1983-08-11 | 1984-08-10 | Process for 2,6-substituted pyridine herbicide |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR8404808A Expired KR870001233B1 (en) | 1983-08-11 | 1984-08-10 | Process for 2,6-substituted pyridine herbicide |
Country Status (33)
| Country | Link |
|---|---|
| EP (1) | EP0135491B1 (enExample) |
| KR (2) | KR890000481B1 (enExample) |
| AT (1) | ATE40262T1 (enExample) |
| AU (1) | AU566077B2 (enExample) |
| BG (1) | BG42832A3 (enExample) |
| BR (1) | BR8404010A (enExample) |
| CA (1) | CA1269383A (enExample) |
| CS (1) | CS261875B2 (enExample) |
| CY (1) | CY1425A (enExample) |
| DD (1) | DD228247A5 (enExample) |
| DE (1) | DE3476319D1 (enExample) |
| DK (1) | DK167732B1 (enExample) |
| ES (1) | ES8506276A1 (enExample) |
| FI (1) | FI82037C (enExample) |
| GB (1) | GB2145085B (enExample) |
| HK (1) | HK30988A (enExample) |
| HU (1) | HU197172B (enExample) |
| IL (1) | IL72640A (enExample) |
| IN (1) | IN160125B (enExample) |
| KE (1) | KE3794A (enExample) |
| MA (1) | MA20199A1 (enExample) |
| MX (1) | MX160550A (enExample) |
| NO (1) | NO166752C (enExample) |
| NZ (1) | NZ209179A (enExample) |
| OA (1) | OA07790A (enExample) |
| PL (1) | PL142320B1 (enExample) |
| PT (1) | PT79062B (enExample) |
| RO (2) | RO93219B (enExample) |
| SG (1) | SG5088G (enExample) |
| SU (1) | SU1565339A3 (enExample) |
| TR (1) | TR22217A (enExample) |
| YU (1) | YU45645B (enExample) |
| ZW (1) | ZW12984A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4771057A (en) * | 1986-02-03 | 1988-09-13 | University Of Alberta | Reduced pyridyl derivatives with cardiovascular regulating properties |
| US4908057A (en) * | 1988-08-01 | 1990-03-13 | Monsanto Company | Substituted 2,6-substituted 1,2- or 1,6-dihydro pyridine compounds |
| EP0448542B1 (en) * | 1990-03-19 | 1995-11-22 | Rohm And Haas Company | Process for preparation of fluoromethyl-substituted dihydropyridine carbodithioates |
| US5116991A (en) * | 1990-03-19 | 1992-05-26 | Monsanto Company | Process for preparation of fluoromethyl-substituted dihydropyridine carbodithioates |
| US5070204A (en) * | 1990-03-19 | 1991-12-03 | Monsanto Company | Process for preparation of fluoromethyl-substituted pyridine dicarboxylates |
| US5099024A (en) * | 1990-03-19 | 1992-03-24 | Monsanto Company | Process for preparation of fluoromethyl-substituted pyridine carbodithioates |
| US5099023A (en) * | 1990-03-19 | 1992-03-24 | Monsanto Company | Process for preparation of fluoromethyl-substituted pyridine carbodithioates |
| US5206369A (en) * | 1992-01-21 | 1993-04-27 | Monsanto Company | Process for the dehydration of dihydroxypiperidinedicarboxylates |
| US6605624B1 (en) | 1998-02-13 | 2003-08-12 | Pharmacia Corporation | Substituted pyridines useful for inhibiting cholesteryl ester transfer protein activity |
-
1984
- 1984-08-09 ES ES535012A patent/ES8506276A1/es not_active Expired
- 1984-08-10 GB GB08420323A patent/GB2145085B/en not_active Expired
- 1984-08-10 CS CS846101A patent/CS261875B2/cs unknown
- 1984-08-10 ZW ZW129/84A patent/ZW12984A1/xx unknown
- 1984-08-10 RO RO122930A patent/RO93219B/ro unknown
- 1984-08-10 NZ NZ209179A patent/NZ209179A/xx unknown
- 1984-08-10 TR TR22217A patent/TR22217A/xx unknown
- 1984-08-10 AU AU31810/84A patent/AU566077B2/en not_active Ceased
- 1984-08-10 OA OA58364A patent/OA07790A/xx unknown
- 1984-08-10 HU HU843062A patent/HU197172B/hu not_active IP Right Cessation
- 1984-08-10 BG BG066569A patent/BG42832A3/xx unknown
- 1984-08-10 FI FI843168A patent/FI82037C/fi not_active IP Right Cessation
- 1984-08-10 NO NO843204A patent/NO166752C/no unknown
- 1984-08-10 EP EP84870118A patent/EP0135491B1/en not_active Expired
- 1984-08-10 KR KR1019840004808D patent/KR890000481B1/ko not_active Expired
- 1984-08-10 IL IL72640A patent/IL72640A/xx not_active IP Right Cessation
- 1984-08-10 DE DE8484870118T patent/DE3476319D1/de not_active Expired
- 1984-08-10 SU SU843783502A patent/SU1565339A3/ru active
- 1984-08-10 YU YU140084A patent/YU45645B/sh unknown
- 1984-08-10 BR BR8404010A patent/BR8404010A/pt unknown
- 1984-08-10 CA CA000460730A patent/CA1269383A/en not_active Expired - Lifetime
- 1984-08-10 IN IN597/MAS/84A patent/IN160125B/en unknown
- 1984-08-10 DK DK385784A patent/DK167732B1/da not_active IP Right Cessation
- 1984-08-10 PT PT79062A patent/PT79062B/pt not_active IP Right Cessation
- 1984-08-10 DD DD84275353A patent/DD228247A5/de not_active IP Right Cessation
- 1984-08-10 MA MA20423A patent/MA20199A1/fr unknown
- 1984-08-10 RO RO84115469A patent/RO89127A/ro unknown
- 1984-08-10 KR KR8404808A patent/KR870001233B1/ko not_active Expired
- 1984-08-10 AT AT84870118T patent/ATE40262T1/de not_active IP Right Cessation
- 1984-08-10 PL PL1984249141A patent/PL142320B1/pl unknown
- 1984-08-10 MX MX5969A patent/MX160550A/es unknown
-
1988
- 1988-01-14 SG SG50/88A patent/SG5088G/en unknown
- 1988-01-25 KE KE3794A patent/KE3794A/xx unknown
- 1988-04-28 HK HK309/88A patent/HK30988A/xx not_active IP Right Cessation
- 1988-09-02 CY CY1425A patent/CY1425A/en unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0133612B1 (en) | Substituted 2,6-substituted pyridine compounds | |
| JPH0323544B2 (enExample) | ||
| JPH082897B2 (ja) | 除草剤として有用な新規な５（および／または６）置換された２―（２―イミダゾリン―２―イル）ニコチン酸類、エステル類および塩類 | |
| KR890000481B1 (ko) | 제초제용 2,6-비스-플루오로메틸-디하이드로피리딘-3,5-디카르복실릭에시드 에스테르의 제조방법 | |
| DE3688110T2 (de) | Pyridinderivate und herbizide Zusammensetzung. | |
| KR890003849B1 (ko) | 치환된 피리딘 제초제 | |
| US4609399A (en) | Substituted 4,6-alkoxy pyridinecarboxylate compounds and herbicidal use | |
| US4554013A (en) | Herbicidal imidazolinyl naphthoic acids | |
| US4658030A (en) | Process for the preparation of 2-(5,5-disubstituted-4-oxo-2-imidazolin-2-yl)nicotinic acids, quinoline-3-carboxylic acids, and benzoic acids | |
| JP2572099B2 (ja) | 除草剤組成物 | |
| JPH0735380B2 (ja) | 置換ピリジン化合物 | |
| CA1236107A (en) | Substituted imidazolinyl benzoic acids, esters and salts and use thereof as herbicidal agents | |
| KR910004429B1 (ko) | 2,6-치환 1,2-또는 1,6-디하이드로피리딘 화합물 | |
| JPH03135941A (ja) | 若干種のグリオキシル―シクロヘキセンジオン化合物 | |
| JP3157173B2 (ja) | ５−複素環式−ピリジン−２，３−ジカルボン酸エステル類のアルキルエステル類、除草剤として有益な５−複素環式２−（２−イミダゾリン−２−イル）ピリジン類およびそれらの製造方法 | |
| US5114465A (en) | Substituted pyridine compounds and herbicidal compositions and methods | |
| US5037469A (en) | Substituted 3- or 5-dialkylamino pyridine compounds | |
| JPS6058961A (ja) | 除草剤組成物 | |
| US5142055A (en) | Method of preparing 2, 6-substituted pyridine compounds | |
| US4741766A (en) | Substituted 4,6-alkoxy pyridinecarboxylate compounds and herbicidal use | |
| JPWO1998029391A1 (ja) | ６−（無置換または置換）フェノキシピコリン酸、その製造方法および農園芸用殺菌剤 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19840810 |
|
| PA0201 | Request for examination | ||
| PG1501 | Laying open of application | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 19860430 Patent event code: PE09021S01D |
|
| PE0601 | Decision on rejection of patent |
Patent event date: 19860922 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 19860430 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |
|
| PJ2001 | Appeal |
Appeal kind category: Appeal against decision to decline refusal Decision date: 19870430 Appeal identifier: 1986201000717 Request date: 19861022 |
|
| PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 19880330 |
|
| PR0701 | Registration of establishment |
Comment text: Registration of Establishment Patent event date: 19880622 Patent event code: PR07011E01D |
|
| PG1605 | Publication of application before grant of patent |
Comment text: Decision on Publication of Application Patent event code: PG16051S01I Patent event date: 19890106 Comment text: Decision on Publication of Application Patent event code: PG16051S01I Patent event date: 19870523 |
|
| PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 19890612 |
|
| PR1002 | Payment of registration fee |
Payment date: 19890823 End annual number: 3 Start annual number: 1 |
|
| PR1001 | Payment of annual fee |
Payment date: 19920206 Start annual number: 4 End annual number: 4 |
|
| PR1001 | Payment of annual fee |
Payment date: 19930219 Start annual number: 5 End annual number: 5 |
|
| PR1001 | Payment of annual fee |
Payment date: 19940309 Start annual number: 6 End annual number: 6 |
|
| PR1001 | Payment of annual fee |
Payment date: 19950222 Start annual number: 7 End annual number: 7 |
|
| PR1001 | Payment of annual fee |
Payment date: 19960221 Start annual number: 8 End annual number: 8 |
|
| PC1903 | Unpaid annual fee |