CA2082574C - 3-isoxazolylphenyl compounds, their preparation and their use - Google Patents

3-isoxazolylphenyl compounds, their preparation and their use Download PDF

Info

Publication number: CA2082574C
Authority: CA; Canada
Prior art keywords: formula; alkyl; compound; methyl; och
Prior art date: 1991-11-18
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 - Fee Related

Application number

CA002082574A

Other languages

English (en)

French (fr)

Other versions

CA2082574A1 (en

Inventor

Stefan Mueller

Hans Theobald

Harald Rang

Volker Harries

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF SE

Original Assignee

BASF SE

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.)

1991-11-18

Filing date

1992-11-10

Publication date

2003-05-13

1992-11-10 Application filed by BASF SE filed Critical BASF SE

1993-05-19 Publication of CA2082574A1 publication Critical patent/CA2082574A1/en

2003-05-13 Application granted granted Critical

2003-05-13 Publication of CA2082574C publication Critical patent/CA2082574C/en

2012-11-10 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

-1 3-isoxazolylphenyl compounds Chemical class 0.000 title claims abstract description 224
238000002360 preparation method Methods 0.000 title claims abstract description 33
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 76
238000000034 method Methods 0.000 claims abstract description 59
230000008569 process Effects 0.000 claims abstract description 50
239000001257 hydrogen Substances 0.000 claims abstract description 32
125000005843 halogen group Chemical group 0.000 claims abstract description 27
229910052736 halogen Inorganic materials 0.000 claims abstract description 20
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
125000003118 aryl group Chemical group 0.000 claims abstract description 13
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 12
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 12
150000002431 hydrogen Chemical group 0.000 claims abstract description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
229910052717 sulfur Inorganic materials 0.000 claims abstract description 10
125000004076 pyridyl group Chemical group 0.000 claims abstract description 9
229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 5
125000001624 naphthyl group Chemical group 0.000 claims abstract description 5
150000001875 compounds Chemical class 0.000 claims description 81
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 30
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 27
229910000077 silane Inorganic materials 0.000 claims description 25
150000003254 radicals Chemical class 0.000 claims description 24
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 23
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
239000003960 organic solvent Substances 0.000 claims description 23
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 22
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 19
150000002367 halogens Chemical group 0.000 claims description 18
150000001340 alkali metals Chemical class 0.000 claims description 17
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
229910001413 alkali metal ion Inorganic materials 0.000 claims description 12
229910001420 alkaline earth metal ion Inorganic materials 0.000 claims description 12
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 9
241000607479 Yersinia pestis Species 0.000 claims description 9
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
229920006395 saturated elastomer Polymers 0.000 claims description 5
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
125000004122 cyclic group Chemical group 0.000 claims description 4
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 3
239000000575 pesticide Substances 0.000 claims description 3
239000011593 sulfur Substances 0.000 claims description 3
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
239000000654 additive Substances 0.000 claims description 2
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 abstract description 11
239000003795 chemical substances by application Substances 0.000 abstract description 9
125000003342 alkenyl group Chemical group 0.000 abstract description 6
125000000753 cycloalkyl group Chemical group 0.000 abstract description 6
125000000304 alkynyl group Chemical group 0.000 abstract description 5
125000003545 alkoxy group Chemical group 0.000 abstract description 2
125000000262 haloalkenyl group Chemical group 0.000 abstract description 2
125000004438 haloalkoxy group Chemical group 0.000 abstract description 2
125000001188 haloalkyl group Chemical group 0.000 abstract description 2
125000000547 substituted alkyl group Chemical group 0.000 abstract 2
125000002947 alkylene group Chemical group 0.000 abstract 1
239000000460 chlorine Substances 0.000 description 172
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 117
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 78
238000006243 chemical reaction Methods 0.000 description 55
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 54
239000000243 solution Substances 0.000 description 44
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
239000000203 mixture Substances 0.000 description 35
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 34
229910052801 chlorine Inorganic materials 0.000 description 34
229910052799 carbon Inorganic materials 0.000 description 30
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 29
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
229910052794 bromium Inorganic materials 0.000 description 25
239000004480 active ingredient Substances 0.000 description 23
125000001424 substituent group Chemical group 0.000 description 23
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 21
239000011737 fluorine Substances 0.000 description 21
229910052731 fluorine Inorganic materials 0.000 description 21
235000019000 fluorine Nutrition 0.000 description 21
229940060037 fluorine Drugs 0.000 description 21
229910052751 metal Inorganic materials 0.000 description 21
239000002184 metal Substances 0.000 description 21
239000002904 solvent Substances 0.000 description 20
239000007858 starting material Substances 0.000 description 20
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 18
101150041968 CDC13 gene Proteins 0.000 description 18
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 18
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 18
239000000741 silica gel Substances 0.000 description 18
229910002027 silica gel Inorganic materials 0.000 description 18
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 17
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 16
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 16
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 15
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 15
238000003756 stirring Methods 0.000 description 15
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 14
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 14
IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 14
229910052744 lithium Inorganic materials 0.000 description 13
239000012074 organic phase Substances 0.000 description 13
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 13
239000011734 sodium Substances 0.000 description 13
229910052708 sodium Inorganic materials 0.000 description 13
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 12
229910052783 alkali metal Inorganic materials 0.000 description 11
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 11
239000003921 oil Substances 0.000 description 11
229910052700 potassium Inorganic materials 0.000 description 11
FIARMZDBEGVMLV-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanolate Chemical group [O-]C(F)(F)C(F)(F)F FIARMZDBEGVMLV-UHFFFAOYSA-N 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
239000002585 base Substances 0.000 description 10
239000003054 catalyst Substances 0.000 description 10
125000000842 isoxazolyl group Chemical group 0.000 description 10
229940073584 methylene chloride Drugs 0.000 description 10
150000002825 nitriles Chemical class 0.000 description 10
238000005160 1H NMR spectroscopy Methods 0.000 description 9
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 9
230000015572 biosynthetic process Effects 0.000 description 9
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 9
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
239000011777 magnesium Substances 0.000 description 9
239000012071 phase Substances 0.000 description 9
238000000746 purification Methods 0.000 description 9
238000003786 synthesis reaction Methods 0.000 description 9
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 8
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
150000004945 aromatic hydrocarbons Chemical class 0.000 description 8
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
238000004440 column chromatography Methods 0.000 description 8
229910052740 iodine Inorganic materials 0.000 description 8
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 8
238000012986 modification Methods 0.000 description 8
230000004048 modification Effects 0.000 description 8
239000003208 petroleum Substances 0.000 description 8
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
239000007787 solid Substances 0.000 description 8
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
239000002253 acid Substances 0.000 description 7
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 7
150000002170 ethers Chemical class 0.000 description 7
150000005826 halohydrocarbons Chemical class 0.000 description 7
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 7
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 7
239000000843 powder Substances 0.000 description 7
239000000047 product Substances 0.000 description 7
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 7
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 7
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 6
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 6
125000004781 2,2-dichloro-2-fluoroethyl group Chemical group [H]C([H])(*)C(F)(Cl)Cl 0.000 description 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
125000004780 2-chloro-2,2-difluoroethyl group Chemical group [H]C([H])(*)C(F)(F)Cl 0.000 description 6
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
235000019445 benzyl alcohol Nutrition 0.000 description 6
150000003938 benzyl alcohols Chemical class 0.000 description 6
125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 6
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 6
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 6
239000006185 dispersion Substances 0.000 description 6
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 6
238000009472 formulation Methods 0.000 description 6
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 6
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 6
125000001190 organyl group Chemical group 0.000 description 6
230000036647 reaction Effects 0.000 description 6
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 6
125000004776 1-fluoroethyl group Chemical group [H]C([H])([H])C([H])(F)* 0.000 description 5
125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 5
125000004779 2-chloro-2-fluoroethyl group Chemical group [H]C([H])(*)C([H])(F)Cl 0.000 description 5
DUNULJXPOJZNHM-UHFFFAOYSA-N 2-methyl-3-(oxan-2-yloxymethyl)benzaldehyde Chemical compound C1=CC=C(C=O)C(C)=C1COC1OCCCC1 DUNULJXPOJZNHM-UHFFFAOYSA-N 0.000 description 5
125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 description 5
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 5
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 5
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 5
238000004821 distillation Methods 0.000 description 5
239000000839 emulsion Substances 0.000 description 5
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 5
125000004705 ethylthio group Chemical group C(C)S* 0.000 description 5
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 5
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 5
FEWLNYSYJNLUOO-UHFFFAOYSA-N 1-Piperidinecarboxaldehyde Chemical compound O=CN1CCCCC1 FEWLNYSYJNLUOO-UHFFFAOYSA-N 0.000 description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
241000244206 Nematoda Species 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
230000009471 action Effects 0.000 description 4
150000001299 aldehydes Chemical class 0.000 description 4
229910052784 alkaline earth metal Inorganic materials 0.000 description 4
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
239000004359 castor oil Substances 0.000 description 4
235000019438 castor oil Nutrition 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
238000001816 cooling Methods 0.000 description 4
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
238000001035 drying Methods 0.000 description 4
238000010410 dusting Methods 0.000 description 4
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 4
239000011261 inert gas Substances 0.000 description 4
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
229910052749 magnesium Inorganic materials 0.000 description 4
150000002739 metals Chemical class 0.000 description 4
150000002902 organometallic compounds Chemical class 0.000 description 4
239000007800 oxidant agent Substances 0.000 description 4
150000002923 oximes Chemical class 0.000 description 4
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 4
229910000105 potassium hydride Inorganic materials 0.000 description 4
125000006239 protecting group Chemical group 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
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MXZQOTDQZBUTHH-UHFFFAOYSA-M [I-].[Mg+]C=C Chemical compound [I-].[Mg+]C=C MXZQOTDQZBUTHH-UHFFFAOYSA-M 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
150000005215 alkyl ethers Chemical class 0.000 description 1
150000008051 alkyl sulfates Chemical class 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
229910000148 ammonium phosphate Inorganic materials 0.000 description 1
235000019289 ammonium phosphates Nutrition 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
239000013011 aqueous formulation Substances 0.000 description 1
125000005228 aryl sulfonate group Chemical group 0.000 description 1
239000003899 bactericide agent Substances 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
HRQGCQVOJVTVLU-UHFFFAOYSA-N bis(chloromethyl) ether Chemical class ClCOCCl HRQGCQVOJVTVLU-UHFFFAOYSA-N 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
235000013877 carbamide Nutrition 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
HJUGFYREWKUQJT-UHFFFAOYSA-N carbon tetrabromide Natural products BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 1
125000005518 carboxamido group Chemical group 0.000 description 1
150000007942 carboxylates Chemical group 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
235000019987 cider Nutrition 0.000 description 1
239000004927 clay Substances 0.000 description 1
239000011280 coal tar Substances 0.000 description 1
NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
JBAKCAZIROEXGK-LNKPDPKZSA-N copper;(z)-4-hydroxypent-3-en-2-one Chemical compound [Cu].C\C(O)=C\C(C)=O JBAKCAZIROEXGK-LNKPDPKZSA-N 0.000 description 1
208000031513 cyst Diseases 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
UWGIJJRGSGDBFJ-UHFFFAOYSA-N dichloromethylsilane Chemical compound [SiH3]C(Cl)Cl UWGIJJRGSGDBFJ-UHFFFAOYSA-N 0.000 description 1
239000002283 diesel fuel Substances 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
MJUJXFBTEFXVKU-UHFFFAOYSA-N diethyl phosphonate Chemical class CCOP(=O)OCC MJUJXFBTEFXVKU-UHFFFAOYSA-N 0.000 description 1
125000006001 difluoroethyl group Chemical group 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
OIKHZBFJHONJJB-UHFFFAOYSA-N dimethyl(phenyl)silicon Chemical compound C[Si](C)C1=CC=CC=C1 OIKHZBFJHONJJB-UHFFFAOYSA-N 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
239000010459 dolomite Substances 0.000 description 1
229910000514 dolomite Inorganic materials 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
150000003948 formamides Chemical class 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
150000004687 hexahydrates Chemical class 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
239000005457 ice water Substances 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
150000002484 inorganic compounds Chemical class 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
238000003780 insertion Methods 0.000 description 1
230000037431 insertion Effects 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000001786 isothiazolyl group Chemical group 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
239000004571 lime Substances 0.000 description 1
239000006028 limestone Substances 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
239000000463 material Substances 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
238000003801 milling Methods 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
229940044654 phenolsulfonic acid Drugs 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003138 primary alcohols Chemical class 0.000 description 1
HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical class C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
230000009467 reduction Effects 0.000 description 1
QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QBERHIJABFXGRZ-UHFFFAOYSA-M 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000004317 sodium nitrate Substances 0.000 description 1
235000010344 sodium nitrate Nutrition 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
230000002311 subsequent effect Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000012360 testing method Methods 0.000 description 1
HJUGFYREWKUQJT-OUBTZVSYSA-N tetrabromomethane Chemical compound Br[13C](Br)(Br)Br HJUGFYREWKUQJT-OUBTZVSYSA-N 0.000 description 1
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
KQBSGRWMSNFIPG-UHFFFAOYSA-N trioxane Chemical compound C1COOOC1 KQBSGRWMSNFIPG-UHFFFAOYSA-N 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
HQYCOEXWFMFWLR-UHFFFAOYSA-K vanadium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[V+3] HQYCOEXWFMFWLR-UHFFFAOYSA-K 0.000 description 1
238000010792 warming Methods 0.000 description 1
239000002023 wood Substances 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring

Landscapes

Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Plant Pathology (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Molecular Biology (AREA)
Biochemistry (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

CA002082574A 1991-11-18 1992-11-10 3-isoxazolylphenyl compounds, their preparation and their use Expired - Fee Related CA2082574C (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE4137940A DE4137940A1 (de)	1991-11-18	1991-11-18	3-isoxazolylphenylverbindungen, ihre herstellung und ihre verwendung
DEP4137940.3		1991-11-18

Publications (2)

Publication Number	Publication Date
CA2082574A1 CA2082574A1 (en)	1993-05-19
CA2082574C true CA2082574C (en)	2003-05-13

Family

ID=6445077

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002082574A Expired - Fee Related CA2082574C (en)	1991-11-18	1992-11-10	3-isoxazolylphenyl compounds, their preparation and their use

Country Status (8)

Country	Link
US (1)	US5256666A (2)
EP (1)	EP0543238B1 (2)
JP (1)	JP3246964B2 (2)
KR (1)	KR100234925B1 (2)
CA (1)	CA2082574C (2)
DE (2)	DE4137940A1 (2)
ES (1)	ES2104794T3 (2)
TW (1)	TW223064B (2)

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AU8127298A (en) *	1997-07-09	1999-02-08	Nippon Soda Co., Ltd.	Isoxazole compounds, process for the preparation thereof, and insecticides and acaricides
MY151199A (en)	2001-11-02	2014-04-30	Rigel Pharmaceuticals Inc	Substituted diphenyl heterocycles useful for treating hcv infection
JP2005511714A (ja)	2001-12-10	2005-04-28	ブリストル−マイヤーズ　スクイブ　カンパニー	Ｒｓｖ融合インヒビターのジ塩酸塩・モノ水和物
BR0313755A (pt) *	2002-08-23	2005-06-21	Rigel Pharmaceuticals Inc	Composto, métodos para inibir a replicação ou proliferação de um vìrion da hepatite c e para tratar ou prevenir uma infecção por hcv, e, composição
US7326790B2 (en) *	2003-05-02	2008-02-05	Rigel Pharmaceuticals, Inc.	Diphenylisoxazole compounds and hydro isomers thereof
US7115642B2 (en)	2003-05-02	2006-10-03	Rigel Pharmaceuticals, Inc.	Substituted diphenyl isoxazoles, pyrazoles and oxadiazoles useful for treating HCV infection
US7220745B2 (en)	2003-05-15	2007-05-22	Rigel Pharmaceuticals	Heterocyclic compounds useful to treat HCV
WO2005049065A2 (en) *	2003-11-19	2005-06-02	Rigel Pharmaceuticals, Inc.	Synergistic combinations of dihaloacetamide with interferon or ribavirin for treatment hcv infections
US7514434B2 (en)	2004-02-23	2009-04-07	Rigel Pharmaceuticals, Inc.	Heterocyclic compounds having an oxadiazole moiety and hydro isomers thereof
WO2005097760A1 (en) *	2004-03-26	2005-10-20	Rigel Pharmaceuticals, Inc.	Heterocyclic anti-viral compounds comprising metabolizable moieties and their uses
CA2606106A1 (en) *	2005-05-02	2007-03-08	Rigel Pharmaceuticals, Inc.	Heterocyclic anti-viral compounds comprising metabolizable moieties and their uses
NL2000351C2 (nl)	2005-12-22	2007-09-11	Pfizer Prod Inc	Estrogeen-modulatoren.
EP2545964A1 (en)	2011-07-13	2013-01-16	Phenex Pharmaceuticals AG	Novel FXR (NR1H4) binding and activity modulating compounds
CA3252823A1 (en)	2016-06-13	2025-02-25	Gilead Sciences, Inc.	Substituted tert-butyl-3-(2-chloro-phenyl)-3-hydroxyazetidine-1-carboxylate compounds
BR112018075734A2 (pt)	2016-06-13	2019-04-02	Gilead Sciences, Inc.	composto, composição farmacêutica, método para tratar um paciente com uma doença ou condição mediada pelo menos em parte por fxr, e, uso de um composto.
CN110461328A (zh)	2017-03-28	2019-11-15	吉利德科学公司	治疗肝疾病的治疗组合
EP4360632B1 (en)	2019-01-15	2025-10-29	Gilead Sciences, Inc.	Fxr (nr1h4) modulating compounds
US11524005B2 (en)	2019-02-19	2022-12-13	Gilead Sciences, Inc.	Solid forms of FXR agonists

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DE3140632A1 (de) *	1981-10-13	1983-04-21	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung von (alpha)-dicyano-trimethylsilyloxy-verbindungen (i)
DE3604781A1 (de) *	1986-02-13	1987-08-27	Schering Ag	Neue silane, verfahren zu ihrer herstellung und diese verbindungen enthaltende einsektizide mittel
CN1025470C (zh) *	1986-05-31	1994-07-20	赫彻斯特股份公司	含新型硅烷衍生物的农药，杀虫剂和杀螨剂组合物
US5185025A (en) *	1988-11-21	1993-02-09	Monsanto Company	Substituted pyrazoles and their use as herbicides

1991
- 1991-11-18 DE DE4137940A patent/DE4137940A1/de not_active Withdrawn
1992
- 1992-11-06 EP EP92119064A patent/EP0543238B1/de not_active Expired - Lifetime
- 1992-11-06 DE DE59208576T patent/DE59208576D1/de not_active Expired - Lifetime
- 1992-11-06 ES ES92119064T patent/ES2104794T3/es not_active Expired - Lifetime
- 1992-11-10 CA CA002082574A patent/CA2082574C/en not_active Expired - Fee Related
- 1992-11-10 TW TW081108969A patent/TW223064B/zh active
- 1992-11-13 US US07/975,733 patent/US5256666A/en not_active Expired - Lifetime
- 1992-11-17 KR KR1019920021571A patent/KR100234925B1/ko not_active Expired - Fee Related
- 1992-11-17 JP JP30686692A patent/JP3246964B2/ja not_active Expired - Fee Related

Also Published As

Publication number	Publication date
KR930010050A (ko)	1993-06-21
ES2104794T3 (es)	1997-10-16
US5256666A (en)	1993-10-26
CA2082574A1 (en)	1993-05-19
TW223064B (2)	1994-05-01
JP3246964B2 (ja)	2002-01-15
EP0543238A1 (de)	1993-05-26
EP0543238B1 (de)	1997-06-04
KR100234925B1 (ko)	1999-12-15
DE4137940A1 (de)	1993-05-19
DE59208576D1 (de)	1997-07-10
JPH05247064A (ja)	1993-09-24

Legal Events

Date	Code	Title	Description
1999-09-22	EEER	Examination request
2008-11-10	MKLA	Lapsed

Publication	Publication Date	Title
US5256666A (en)	1993-10-26	3-Isoxazolylphenyl compounds, their preparation and their use
HU213444B (en)	1997-06-30	Insecticidal, acaricidal and fungicidal composition comprising phenylacrylic acid derivatives and process for producing the active ingredients and using the compositions
SK280714B6 (sk)	2000-06-12	Orto-substituované amidy kyseliny fenyloctovej, fu
US5151441A (en)	1992-09-29	3-isoxazolylbenzyl esters, their preparation and their use
AU684640B2 (en)	1997-12-18	Pyrazolyl derivatives, their preparation and their use
AU648193B2 (en)	1994-04-14	Alpha-arylacrylic acid derivatives, their preparation and use for controlling pests and fungi
CA2048983A1 (en)	1992-03-08	.alpha.-arylacrylic acid derivatives, their preparation and their use for controlling pests and fungi
US5110829A (en)	1992-05-05	2,2'-thienylbenzothiophenes, their preparation and their use for controlling pests
US5190963A (en)	1993-03-02	Cyclopropane(thio)carboxamides, the preparation thereof and intermediates therefor, and the use thereof for controlling pests
CA1337698C (en)	1995-12-05	Pyrethroids and their use for controlling pests
KR0178395B1 (ko)	1999-03-20	히드로퀴논 디에테르, 그의 제조 방법 및 그의 해충 박멸 용도
JP2806439B2 (ja)	1998-09-30	シクロプロパンチオカルボン酸アミド
IL98082A (en)	1994-12-29	Benzyl esters of ortho-converted cyclopropanecarbosylic acid, their preparation and use as pesticides
US5389656A (en)	1995-02-14	Acetylene derivatives, their preparation and their use for controlling insects and acaridae
CA2040752A1 (en)	1991-10-20	Hydroquinone diethers, their preparation and their use
CA2011088A1 (en)	1990-09-04	Substituted benzyl 2-phenyl-1-alk(en)ylcyclopropane-carboxylates and the use thereof for controlling pests
EP0473041A1 (de)	1992-03-04	2,3-Dihydrobenzofurylmethylester, ihre Herstellung und sie enthaltende Mittel zur Bekämpfung von Schädlingen
CZ155394A3 (en)	1995-02-15	Thiophenes and polythiophenes, process of their preparation and use
KR100372212B1 (ko)	2005-10-25	페닐아세트산유도체,이의제조방법및이를함유하는조성물
CA2023035A1 (en)	1991-02-20	Dihalovinylbenzyl esters, their preparation, intermediates for their preparation and their use for controlling pests
DE4210281A1 (de)	1992-10-15	1,2,4-triazol-5-yl-phosphorsaeuren bzw. -phosphonsaeuren, verfahren zu ihrer herstellung und ihre verwendung zur schaedlingsbekaempfung