LV10443B - Heterocyclic compounds - Google Patents

Heterocyclic compounds Download PDF

Info

Publication number: LV10443B
Authority: LV; Latvia
Prior art keywords: methyl; phthalide; alkyl; oxy; alkoxy
Prior art date: 1989-10-12

Application number

LVP-93-890A

Other languages

English (en)

Latvian (lv)

Other versions

LV10443A (lv

Inventor

Lethy Christoph

Obrecht Jeanne-Pierre

Original Assignee

Ciba Geigy Ag

Priority date (The priority date 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 date listed.)

1989-10-12

Filing date

1993-06-30

Publication date

1996-04-20

1993-06-30 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1995-02-20 Publication of LV10443A publication Critical patent/LV10443A/xx

1996-04-20 Publication of LV10443B publication Critical patent/LV10443B/lv

Links

150000002391 heterocyclic compounds Chemical class 0.000 title claims 2
150000001875 compounds Chemical class 0.000 claims abstract description 26
-1 N-methoxymethylamino Chemical group 0.000 claims description 143
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 45
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 41
125000000217 alkyl group Chemical group 0.000 claims description 28
229910052760 oxygen Inorganic materials 0.000 claims description 26
239000001301 oxygen Substances 0.000 claims description 26
125000003545 alkoxy group Chemical group 0.000 claims description 23
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 22
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
239000011737 fluorine Substances 0.000 claims description 14
229910052731 fluorine Inorganic materials 0.000 claims description 14
229910052736 halogen Inorganic materials 0.000 claims description 14
239000000460 chlorine Substances 0.000 claims description 13
229910052801 chlorine Inorganic materials 0.000 claims description 13
150000002367 halogens Chemical group 0.000 claims description 13
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
125000001309 chloro group Chemical group Cl* 0.000 claims description 10
229910052757 nitrogen Inorganic materials 0.000 claims description 10
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 9
125000004414 alkyl thio group Chemical group 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 6
125000004423 acyloxy group Chemical group 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 5
125000001153 fluoro group Chemical group F* 0.000 claims description 5
230000002363 herbicidal effect Effects 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
239000004009 herbicide Substances 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims 17
229910052739 hydrogen Inorganic materials 0.000 claims 17
150000002431 hydrogen Chemical class 0.000 claims 9
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
125000003282 alkyl amino group Chemical group 0.000 claims 2
125000005115 alkyl carbamoyl group Chemical group 0.000 claims 2
125000000304 alkynyl group Chemical group 0.000 claims 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
125000001246 bromo group Chemical group Br* 0.000 claims 2
125000004428 fluoroalkoxy group Chemical group 0.000 claims 2
125000004970 halomethyl group Chemical group 0.000 claims 2
210000002966 serum Anatomy 0.000 claims 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
239000000654 additive Substances 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
239000013543 active substance Substances 0.000 abstract 3
241000196324 Embryophyta Species 0.000 abstract 2
238000004519 manufacturing process Methods 0.000 abstract 1
230000008635 plant growth Effects 0.000 abstract 1
239000005648 plant growth regulator Substances 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 62
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 56
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
239000000047 product Substances 0.000 description 30
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 27
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 26
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
239000000203 mixture Substances 0.000 description 25
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
238000005160 1H NMR spectroscopy Methods 0.000 description 22
238000006243 chemical reaction Methods 0.000 description 22
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 21
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 21
239000000243 solution Substances 0.000 description 19
WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 18
238000000034 method Methods 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 16
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
238000002329 infrared spectrum Methods 0.000 description 16
239000011780 sodium chloride Substances 0.000 description 16
239000011541 reaction mixture Substances 0.000 description 14
239000000725 suspension Substances 0.000 description 14
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000013078 crystal Substances 0.000 description 11
229910052943 magnesium sulfate Inorganic materials 0.000 description 11
235000019341 magnesium sulphate Nutrition 0.000 description 11
239000012074 organic phase Substances 0.000 description 11
239000000741 silica gel Substances 0.000 description 11
229910002027 silica gel Inorganic materials 0.000 description 11
125000004093 cyano group Chemical group *C#N 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
239000000843 powder Substances 0.000 description 10
241000239290 Araneae Species 0.000 description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
125000001424 substituent group Chemical group 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 8
241000283690 Bos taurus Species 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 8
238000001914 filtration Methods 0.000 description 8
239000000499 gel Substances 0.000 description 8
239000012071 phase Substances 0.000 description 8
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 7
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 7
238000004587 chromatography analysis Methods 0.000 description 7
238000009472 formulation Methods 0.000 description 7
150000003839 salts Chemical class 0.000 description 7
239000011734 sodium Substances 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
239000007921 spray Substances 0.000 description 7
238000003786 synthesis reaction Methods 0.000 description 7
GOGLITPCMXUGIC-UHFFFAOYSA-N 3,7-dihydroxy-3h-2-benzofuran-1-one Chemical compound C1=CC=C(O)C2=C1C(O)OC2=O GOGLITPCMXUGIC-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 6
239000012141 concentrate Substances 0.000 description 6
239000003995 emulsifying agent Substances 0.000 description 6
238000000605 extraction Methods 0.000 description 6
239000008187 granular material Substances 0.000 description 6
235000012054 meals Nutrition 0.000 description 6
229950010765 pivalate Drugs 0.000 description 6
XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 5
AXGFDUVCBOFWKW-UHFFFAOYSA-N 7-(4,6-dimethoxypyrimidin-2-yl)oxy-3-hydroxy-3h-2-benzofuran-1-one Chemical compound COC1=CC(OC)=NC(OC=2C=3C(=O)OC(O)C=3C=CC=2)=N1 AXGFDUVCBOFWKW-UHFFFAOYSA-N 0.000 description 5
FSFLSSMPDXEBGX-UHFFFAOYSA-N 7-hydroxy-3-propan-2-ylidene-2-benzofuran-1-one Chemical compound C1=CC=C(O)C2=C1C(=C(C)C)OC2=O FSFLSSMPDXEBGX-UHFFFAOYSA-N 0.000 description 5
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
239000002585 base Substances 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
239000000284 extract Substances 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
235000011181 potassium carbonates Nutrition 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 5
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
229920002554 vinyl polymer Polymers 0.000 description 5
MWYPSNYTVWEVQU-UHFFFAOYSA-N 3-chloro-7-(4,6-dimethoxypyrimidin-2-yl)oxy-3h-2-benzofuran-1-one Chemical compound COC1=CC(OC)=NC(OC=2C=3C(=O)OC(Cl)C=3C=CC=2)=N1 MWYPSNYTVWEVQU-UHFFFAOYSA-N 0.000 description 4
URTPDSARMPGSPA-UHFFFAOYSA-N 3-hydroxy-7-methoxy-3h-2-benzofuran-1-one Chemical compound COC1=CC=CC2=C1C(=O)OC2O URTPDSARMPGSPA-UHFFFAOYSA-N 0.000 description 4
MVFVFOUVVUJBHX-UHFFFAOYSA-N 7-hydroxy-3-methyl-3H-2-benzofuran-1-thione Chemical compound C1=CC=C(O)C2=C1C(C)OC2=S MVFVFOUVVUJBHX-UHFFFAOYSA-N 0.000 description 4
JXFGWOKQZVKZHY-UHFFFAOYSA-N 7-hydroxy-3-methyl-3h-2-benzofuran-1-one Chemical compound C1=CC=C(O)C2=C1C(C)OC2=O JXFGWOKQZVKZHY-UHFFFAOYSA-N 0.000 description 4
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
206010013786 Dry skin Diseases 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 4
239000006185 dispersion Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
150000002576 ketones Chemical class 0.000 description 4
IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 4
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
125000005499 phosphonyl group Chemical group 0.000 description 4
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
235000011121 sodium hydroxide Nutrition 0.000 description 4
239000007787 solid Substances 0.000 description 4
125000000446 sulfanediyl group Chemical group *S* 0.000 description 4
SZQDQKZMLVXROI-UHFFFAOYSA-N 3-ethenyl-7-hydroxy-3h-2-benzofuran-1-one Chemical compound OC1=CC=CC2=C1C(=O)OC2C=C SZQDQKZMLVXROI-UHFFFAOYSA-N 0.000 description 3
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
239000005995 Aluminium silicate Substances 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
241000282898 Sus scrofa Species 0.000 description 3
235000012211 aluminium silicate Nutrition 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
244000038559 crop plants Species 0.000 description 3
YKNMBTZOEVIJCM-UHFFFAOYSA-N dec-2-ene Chemical compound CCCCCCCC=CC YKNMBTZOEVIJCM-UHFFFAOYSA-N 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
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 3
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 3
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
239000002002 slurry Substances 0.000 description 3
229940083608 sodium hydroxide Drugs 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
239000011593 sulfur Substances 0.000 description 3
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
125000006012 2-chloroethoxy group Chemical group 0.000 description 2
MILFDCFEPYHWDD-UHFFFAOYSA-N 3-hydroxy-7-methoxy-3-(trifluoromethyl)-2-benzofuran-1-one Chemical compound COC1=CC=CC2=C1C(=O)OC2(O)C(F)(F)F MILFDCFEPYHWDD-UHFFFAOYSA-N 0.000 description 2
HUNFAVKUESOLNK-UHFFFAOYSA-N 3-hydroxy-7-methoxy-3-methyl-2-benzofuran-1-one Chemical compound COC1=CC=CC2=C1C(=O)OC2(C)O HUNFAVKUESOLNK-UHFFFAOYSA-N 0.000 description 2
SVQCSALZXQAAJR-UHFFFAOYSA-N 7-(4,6-dimethoxypyrimidin-2-yl)oxy-3-methyl-3h-2-benzofuran-1-one Chemical compound COC1=CC(OC)=NC(OC=2C=3C(=O)OC(C)C=3C=CC=2)=N1 SVQCSALZXQAAJR-UHFFFAOYSA-N 0.000 description 2
OFGSPIFLSGXINH-UHFFFAOYSA-N 7-(4,6-dimethoxypyrimidin-2-yl)oxy-3-methyl-3h-2-benzofuran-1-thione Chemical compound COC1=CC(OC)=NC(OC=2C=3C(=S)OC(C)C=3C=CC=2)=N1 OFGSPIFLSGXINH-UHFFFAOYSA-N 0.000 description 2
FYRJNKSSIDLQOX-UHFFFAOYSA-N 7-hydroxy-3-(trifluoromethyl)-3h-2-benzofuran-1-one Chemical compound OC1=CC=CC2=C1C(=O)OC2C(F)(F)F FYRJNKSSIDLQOX-UHFFFAOYSA-N 0.000 description 2
NRBJGSOXVJPULT-UHFFFAOYSA-N 7-hydroxy-3-methoxy-3-methyl-2-benzofuran-1-one Chemical compound C1=CC=C(O)C2=C1C(OC)(C)OC2=O NRBJGSOXVJPULT-UHFFFAOYSA-N 0.000 description 2
JDICZELAXBTHLX-UHFFFAOYSA-N 7-hydroxy-3-methoxy-3h-2-benzofuran-1-one Chemical compound C1=CC=C(O)C2=C1C(OC)OC2=O JDICZELAXBTHLX-UHFFFAOYSA-N 0.000 description 2
HTHOZQIEDJABIC-UHFFFAOYSA-N 7-hydroxy-3-propan-2-yl-3h-2-benzofuran-1-one Chemical compound C1=CC=C(O)C2=C1C(C(C)C)OC2=O HTHOZQIEDJABIC-UHFFFAOYSA-N 0.000 description 2
PTWPWUVEQZXOFJ-UHFFFAOYSA-N 7-hydroxy-3h-2-benzofuran-1-one Chemical compound OC1=CC=CC2=C1C(=O)OC2 PTWPWUVEQZXOFJ-UHFFFAOYSA-N 0.000 description 2
GJSMLKPYZPFTCG-UHFFFAOYSA-N 8-hydroxy-3-methylisochromen-1-one Chemical compound C1=CC(O)=C2C(=O)OC(C)=CC2=C1 GJSMLKPYZPFTCG-UHFFFAOYSA-N 0.000 description 2
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229910019142 PO4 Inorganic materials 0.000 description 1
235000011999 Panicum crusgalli Nutrition 0.000 description 1
244000292693 Poa annua Species 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
NWQXYQUFNNDNES-UHFFFAOYSA-N S(=O)(=O)(O)O.C(CCCCCCCCCCCCCCC)[Na] Chemical compound S(=O)(=O)(O)O.C(CCCCCCCCCCCCCCC)[Na] NWQXYQUFNNDNES-UHFFFAOYSA-N 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
240000002439 Sorghum halepense Species 0.000 description 1
240000006694 Stellaria media Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
244000098338 Triticum aestivum Species 0.000 description 1
241000251539 Vertebrata <Metazoa> Species 0.000 description 1
FZNCGRZWXLXZSZ-CIQUZCHMSA-N Voglibose Chemical compound OCC(CO)N[C@H]1C[C@](O)(CO)[C@@H](O)[C@H](O)[C@H]1O FZNCGRZWXLXZSZ-CIQUZCHMSA-N 0.000 description 1
ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
239000006096 absorbing agent Substances 0.000 description 1
WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical compound CC(=O)CC(O)=O WDJHALXBUFZDSR-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
239000002253 acid Substances 0.000 description 1
239000012190 activator Substances 0.000 description 1
229940072056 alginate Drugs 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 1
125000005599 alkyl carboxylate group Chemical group 0.000 description 1
125000005037 alkyl phenyl group Chemical group 0.000 description 1
125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
150000008052 alkyl sulfonates Chemical class 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
125000005211 alkyl trimethyl ammonium group Chemical group 0.000 description 1
125000005466 alkylenyl group Chemical group 0.000 description 1
150000001409 amidines Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
125000005228 aryl sulfonate group Chemical group 0.000 description 1
JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
244000052616 bacterial pathogen Species 0.000 description 1
235000013871 bee wax Nutrition 0.000 description 1
235000015278 beef Nutrition 0.000 description 1
239000012166 beeswax Substances 0.000 description 1
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
239000012965 benzophenone Substances 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
238000003339 best practice Methods 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
ABQPEYRVNHDPIO-UHFFFAOYSA-N bromo(dimethyl)borane Chemical compound CB(C)Br ABQPEYRVNHDPIO-UHFFFAOYSA-N 0.000 description 1
JIJAYWGYIDJVJI-UHFFFAOYSA-N butyl naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)OCCCC)=CC=CC2=C1 JIJAYWGYIDJVJI-UHFFFAOYSA-N 0.000 description 1
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
229940071162 caseinate Drugs 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
230000021615 conjugation Effects 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
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230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
238000006477 desulfuration reaction Methods 0.000 description 1
230000023556 desulfurization Effects 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
235000015872 dietary supplement Nutrition 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
RZHBMYQXKIDANM-UHFFFAOYSA-N dioctyl butanedioate;sodium Chemical compound [Na].CCCCCCCCOC(=O)CCC(=O)OCCCCCCCC RZHBMYQXKIDANM-UHFFFAOYSA-N 0.000 description 1
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239000003814 drug Substances 0.000 description 1
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230000003628 erosive effect Effects 0.000 description 1
ZINJLDJMHCUBIP-UHFFFAOYSA-N ethametsulfuron-methyl Chemical compound CCOC1=NC(NC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(=O)OC)=N1 ZINJLDJMHCUBIP-UHFFFAOYSA-N 0.000 description 1
ZQXDUKMRLYGEHT-UHFFFAOYSA-N ethene hydrochloride Chemical compound Cl.C=C.C=C ZQXDUKMRLYGEHT-UHFFFAOYSA-N 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
MHENVRWNXCCIFX-UHFFFAOYSA-N iso-ochracein Natural products C1=CC=C(O)C2=C1C(CC)OC2=O MHENVRWNXCCIFX-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
229910001512 metal fluoride Inorganic materials 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
238000005272 metallurgy Methods 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
IXPQASPTEVXGDK-UHFFFAOYSA-N methyl 2-[[4-(4,6-dimethoxypyrimidin-2-yl)oxy-3-oxo-1h-2-benzofuran-1-yl]oxy]acetate Chemical compound COC(=O)COC1OC(=O)C2=C1C=CC=C2OC1=NC(OC)=CC(OC)=N1 IXPQASPTEVXGDK-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
125000006606 n-butoxy group Chemical group 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite group Chemical group N(=O)[O-] IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
235000016709 nutrition Nutrition 0.000 description 1
230000035764 nutrition Effects 0.000 description 1
235000020824 obesity Nutrition 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
RSGQDDSQLCROIY-UHFFFAOYSA-N oxolane;n,n,n',n'-tetramethylethane-1,2-diamine Chemical compound C1CCOC1.CN(C)CCN(C)C RSGQDDSQLCROIY-UHFFFAOYSA-N 0.000 description 1
SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical class [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 1
239000003973 paint Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
RKHQZMOCQHXUBC-UHFFFAOYSA-N phenol;potassium Chemical compound [K].OC1=CC=CC=C1 RKHQZMOCQHXUBC-UHFFFAOYSA-N 0.000 description 1
WBZFMJOAUABCPY-UHFFFAOYSA-N phenyl oxirane-2-carboxylate Chemical compound C1OC1C(=O)OC1=CC=CC=C1 WBZFMJOAUABCPY-UHFFFAOYSA-N 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000002574 poison Substances 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
238000006068 polycondensation reaction Methods 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
239000002243 precursor Substances 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
FJULTOAMYRARJB-UHFFFAOYSA-N s-[(1-methyl-3-oxo-1h-2-benzofuran-4-yl)] n,n-dimethylcarbamothioate Chemical compound C1=CC=C(SC(=O)N(C)C)C2=C1C(C)OC2=O FJULTOAMYRARJB-UHFFFAOYSA-N 0.000 description 1
235000019515 salmon Nutrition 0.000 description 1
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229920005552 sodium lignosulfonate Polymers 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 1
210000002023 somite Anatomy 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
239000005526 vasoconstrictor agent Substances 0.000 description 1
238000012795 verification Methods 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1
229940082509 xanthan gum Drugs 0.000 description 1

Classifications

- 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
- C07D405/12—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 linked by a chain containing hetero atoms as chain links
- 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
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
- 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
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
- 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
- C07D409/12—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 linked by a chain containing hetero atoms as chain links

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)
Plural Heterocyclic Compounds (AREA)

LVP-93-890A 1989-10-12 1993-06-30 Heterocyclic compounds LV10443B (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH371689		1989-10-12
PCT/CH1990/000222 WO1991005781A1 (fr)	1989-10-12	1990-09-19	Derives de pyrimidine et de triazine a effet herbicide et regulateur de la croissance vegetale

Publications (2)

Publication Number	Publication Date
LV10443A LV10443A (lv)	1995-02-20
LV10443B true LV10443B (en)	1996-04-20

Family

ID=4261971

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LVP-93-890A LV10443B (en)	1989-10-12	1993-06-30	Heterocyclic compounds

Country Status (13)

Country	Link
US (2)	US5332717A (fr)
EP (1)	EP0447506B1 (fr)
JP (1)	JP2990377B2 (fr)
KR (1)	KR0172947B1 (fr)
AU (1)	AU635069B2 (fr)
BR (1)	BR9006950A (fr)
CA (1)	CA2044135A1 (fr)
DE (1)	DE59007567D1 (fr)
ES (1)	ES2063374T3 (fr)
LT (1)	LT3908B (fr)
LV (1)	LV10443B (fr)
RU (1)	RU1838310C (fr)
WO (1)	WO1991005781A1 (fr)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5541148A (en) *	1992-07-08	1996-07-30	Ciba-Geigy Corporation	Selective safened herbicidal composition comprising 2-ethoxycarbonyl-3-(4,6-dimethoxypyrimidine-2-yl) oxy-pyridine and an acylsulfamoylphenyl-urea safener
US5411935A (en) *	1993-03-17	1995-05-02	Sumitomo Chemical Co., Ltd.	Dihydrobenzofuran derivatives, their production and use
MY116568A (en) *	1995-10-13	2004-02-28	Syngenta Participations Ag	Herbicidal synergistic composition, and method controlling weeds
WO2000046212A1 (fr) *	1999-02-05	2000-08-10	Syngenta Participations Ag	Procede de production de derives de pyrimidine substitues
BR0110805B1 (pt) *	2000-05-17	2014-10-14	Syngenta Participations Ag	Processo para a preparação de compostos de anilina
UA75374C2 (uk) *	2000-10-11	2006-04-17	Сінгента Партісіпейшнс Аг	Спосіб одержання тіофенолів
AR033765A1 (es) *	2001-05-22	2004-01-07	Syngenta Participations Ag	Procedimiento para la preparacion de derivados 3-alquil-3h-isobenzofuran-1-ona 7-sustituidos.
DE10142336A1 (de) *	2001-08-30	2003-03-20	Bayer Cropscience Ag	Selektive Herbizide enthaltend ein Tetrazolinon-Derivat
EP2052608A1 (fr)	2007-10-24	2009-04-29	Bayer CropScience AG	Combinaison d'herbicide
DE102008037631A1 (de)	2008-08-14	2010-02-18	Bayer Cropscience Ag	Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden
US8474742B2 (en) *	2009-07-30	2013-07-02	Adc Telecommunications, Inc.	Spool for telecommunications cable and method
PL2627183T5 (pl)	2010-10-15	2024-02-05	Bayer Cropscience Aktiengesellschaft	Zastosowanie herbicydów inhibitorów ALS do kontroli niechcianej roślinności w roślinach Beta vulgaris z tolerancją herbicydów inhibitorów ALS
PE20141468A1 (es)	2010-12-21	2014-11-05	Bayer Cropscience Lp	Mutantes tipo papel de lija de bacillus y metodos de uso de los mismo para mejorar el crecimiento vegetal, promover la salud de plantas y controlar enfermedades y plagas
UA117447C2 (uk)	2011-05-04	2018-08-10	Байєр Інтеллектуал Проперті Гмбх	Застосування гербіцидів інгібіторів als для боротьби з небажаною рослинністю на площі вирощування brassica
MX2014002890A (es)	2011-09-12	2015-01-19	Bayer Cropscience Lp	Metodo para mejorar la salud y/o promover el crecimiento de una planta y/o mejorar la maduracion de frutos.
RS57806B2 (sr)	2012-12-13	2022-07-29	Bayer Cropscience Ag	Upotreba als inhibitora herbicida za kontrolu neželjene vegetacije kod beta vulgaris biljaka tolerantnih na als inhibitore herbicida
KR102282322B1 (ko) *	2013-12-26	2021-07-26	고쿠리츠 다이가쿠 호진 교토 다이가쿠	바퀴벌레 집합 유인 물질, 바퀴벌레 집합 유인제 및 바퀴벌레 구제제
JP6538077B2 (ja)	2014-04-23	2019-07-03	ビーエーエスエフソシエタス・ヨーロピアＢａｓｆＳｅ	除草剤としてのジアミノトリアジン化合物
CN104186476B (zh) *	2014-04-30	2017-07-28	广东中迅农科股份有限公司	一种含有双环磺草酮和环酯草醚的除草组合物
CN110785413B (zh) *	2017-05-02	2024-08-02	Fmc公司	作为除草剂的嘧啶氧基苯并稠合化合物
WO2023062184A1 (fr)	2021-10-15	2023-04-20	KWS SAAT SE & Co. KGaA	Mutants de bêta vulgaris tolérants aux herbicides inhibiteurs de l'als
CN118834183A (zh) *	2023-04-23	2024-10-25	中国医学科学院药物研究所	(z)-3-丁烯基苯酞5位或7位衍生物及其制备方法、用途和药物组合物

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US542564A (en)		1895-07-09		Line-reel
NZ188244A (en) *	1977-09-13	1981-04-24	Ici Australia Ltd	2-substituted pyrimidines compositions growth regulating processes
EP0145078B1 (fr) *	1983-12-02	1988-10-12	Shell Internationale Researchmaatschappij B.V.	Diphényl éthers herbicides
EP0223406B1 (fr) *	1985-10-15	1990-08-29	Kumiai Chemical Industry Co., Ltd.	Dérivés de pyrimidine et leurs applications comme herbicide
US4696695A (en)	1985-10-25	1987-09-29	Ppg Industries, Inc.	Sulfamoyl urea derivatives
JPH082883B2 (ja) *	1986-06-06	1996-01-17	クミアイ化学工業株式会社	２−フエノキシピリミジン誘導体および除草剤
JPS632368A (ja)	1986-06-23	1988-01-07	Nippon Telegr & Teleph Corp <Ntt>	半導体装置およびその製造方法
DE3854099T2 (de) *	1987-04-14	1996-04-04	Ihara Chemical Ind Co	2-Phenoxy-pyrimidin-Derivate und herbizide Zusammensetzung.
DE3851773T2 (de) *	1987-04-14	1995-04-20	Ihara Chemical Ind Co	2-Phenoxypyrimidin-Derivate und herbizide Zusammensetzungen.
US4911754A (en) *	1987-07-16	1990-03-27	American Cyanamid Company	Herbicidally active aryloxy saturated 5-membered benzo fused hetero-cyclic compounds
US4923501A (en) *	1987-11-04	1990-05-08	Kumiai Chemical Industry Co., Ltd.	Pyrimidine derivatives, processes for their production, and herbicidal method and compositions
GB8808071D0 (en) *	1988-04-07	1988-05-11	Shell Int Research	Triazine herbicides
GB8912700D0 (en) *	1989-06-02	1989-07-19	Shell Int Research	Herbicidal compounds
DK0411153T3 (fr)	1989-02-20	1997-02-10	Idemitsu Kosan Co
PH27460A (en) *	1989-12-28	1993-07-09	Kumiai Chemical Industry Co	Pyrimidine derivatives and herbicidal composition containing the same
DE4002365A1 (de) *	1990-01-25	1991-08-01	Schering Ag	Substituierte (beta)-pyrimidinyloxy(thio)- und (beta)-triazinyloxy(thio)cycloalkylcarbonsaeurederivate, verfahren zu ihrer herstellung und ihre verwendung als mittel mit herbizider, fungizider und pflanzenwachstumsregulierender wirkung
AU642753B2 (en) *	1990-07-24	1993-10-28	Mitsubishi Petrochemical Company Limited	Halogen-containing compounds, herbicidal composition containing the same as an active ingredient, and intermediary compounds therefor

1990
- 1990-09-19 AU AU63471/90A patent/AU635069B2/en not_active Ceased
- 1990-09-19 WO PCT/CH1990/000222 patent/WO1991005781A1/fr not_active Ceased
- 1990-09-19 CA CA002044135A patent/CA2044135A1/fr not_active Abandoned
- 1990-09-19 KR KR1019910700589A patent/KR0172947B1/ko not_active Expired - Lifetime
- 1990-09-19 ES ES90913234T patent/ES2063374T3/es not_active Expired - Lifetime
- 1990-09-19 BR BR909006950A patent/BR9006950A/pt not_active IP Right Cessation
- 1990-09-19 EP EP90913234A patent/EP0447506B1/fr not_active Expired - Lifetime
- 1990-09-19 JP JP2512341A patent/JP2990377B2/ja not_active Expired - Lifetime
- 1990-09-19 DE DE59007567T patent/DE59007567D1/de not_active Expired - Fee Related
1991
- 1991-06-11 RU SU914895875A patent/RU1838310C/ru active
1993
- 1993-04-15 US US08/047,888 patent/US5332717A/en not_active Expired - Lifetime
- 1993-06-30 LV LVP-93-890A patent/LV10443B/lv unknown
1994
- 1994-01-31 LT LTIP1847A patent/LT3908B/lt not_active IP Right Cessation
- 1994-05-13 US US08/242,527 patent/US5428002A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
DE59007567D1 (de)	1994-12-01
BR9006950A (pt)	1991-12-10
AU635069B2 (en)	1993-03-11
LTIP1847A (en)	1995-08-25
EP0447506B1 (fr)	1994-10-26
ES2063374T3 (es)	1995-01-01
KR0172947B1 (ko)	1999-02-01
RU1838310C (ru)	1993-08-30
AU6347190A (en)	1991-05-16
EP0447506A1 (fr)	1991-09-25
JP2990377B2 (ja)	1999-12-13
US5428002A (en)	1995-06-27
JPH04504265A (ja)	1992-07-30
US5332717A (en)	1994-07-26
KR920701196A (ko)	1992-08-11
LT3908B (en)	1996-04-25
WO1991005781A1 (fr)	1991-05-02
CA2044135A1 (fr)	1991-04-13
LV10443A (lv)	1995-02-20

Publication	Publication Date	Title
LV10443B (en)	1996-04-20	Heterocyclic compounds
DE69705821T2 (de)	2001-11-08	N-((1,2,4)triazoloazinyl)benzolsulfonamid- und pyridinsulfonamidverbindungen und deren verwendung als herbizide
DE69125667T2 (de)	1997-09-25	Pyrimidin-Derivate und diese enthaltende herbizide Zusammensetzungen
DE60026318T2 (de)	2006-08-10	Isoxazolin derivate und herbizide, die diese als aktiven bestandteil enthalten
DE2715786C2 (fr)	1987-11-05
DE3854099T2 (de)	1996-04-04	2-Phenoxy-pyrimidin-Derivate und herbizide Zusammensetzung.
EP0353640A2 (fr)	1990-02-07	N-acylsulfonamides hétérocycliques, procédé pour leur préparation, agents les contenant et leur utilisation comme herbicides régulateurs de croissance des plantes
EP4305025A1 (fr)	2024-01-17	Amides d'acide n-(1,3,4-oxadiazole-2-yl)phényl-carboxylique chiraux et leur utilisation en tant qu'herbicides
DE68906324T2 (de)	1993-10-21	Substituierte Phenyltriazolopyrimidine als Herbizide.
EP0521500A1 (fr)	1993-01-07	Sel de pyridylsulfonylurées comme herbicides et régulateurs de croissance des plantes, procédé pour leur préparation et leur utilisation
DE69104061T2 (de)	1995-03-30	Substituierte n-heterobicyclische herbizide.
DE2803991A1 (de)	1978-08-10	Sulfonate, verfahren zu deren herstellung und herbizide zusammensetzungen
DE3935277A1 (de)	1991-05-02	Sulfonierte heterocyclische carboxamide, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung als herbizide oder wachstumsregulatoren
DE69837621T2 (de)	2007-12-27	Substituierte pyrimidine und pyridine als unkrautbekämpfungsmittel
DE3887819T2 (de)	1994-09-15	Herbizide Pyridinsulfonylharnstoffe.
DE68919731T2 (de)	1995-07-06	Pyrimidin-Derivate, Verfahren zu deren Herstellung und diese enthaltende herbizide Zusammensetzungen.
DE3325488A1 (de)	1984-02-09	N-phenylpyrazolderivate und ihre verwendung als herbicide
NZ209161A (en)	1987-10-30	Pyridazinylcarboxylic acid and plant gametocidal compositions
DE69419180T2 (de)	1999-10-14	Nikotinsäurederivate und herbizide
US5127936A (en)	1992-07-07	Substituted phenyltriazolopyrimidine herbicides
EP3393244B1 (fr)	2019-12-18	Derives de 2-amino-5-cetoxime-pyrimidine et leur utilisation pour lutter contre la croissance indesirable de plantes
DE3226496A1 (de)	1983-03-24	N-phenylpyrazolderivate
WO2017178314A1 (fr)	2017-10-19	Dérivés de l'acide 3-phényltétramique condensés à action herbicide
EP3475273B1 (fr)	2021-02-24	Derives de 3-amino-1, 2, 4 triazine et leur utilisation pour lutter contre la croissance indesirable de plantes
DE19909541A1 (de)	1999-10-14	Herbizide 2-Aryloxy- bzw. 2-Arylthio-6-arylpyrimidine