JP2008531486A5 - - Google Patents

Info

Publication number

JP2008531486A5

JP2008531486A5 JP2007555500A JP2007555500A JP2008531486A5 JP 2008531486 A5 JP2008531486 A5 JP 2008531486A5 JP 2007555500 A JP2007555500 A JP 2007555500A JP 2007555500 A JP2007555500 A JP 2007555500A JP 2008531486 A5 JP2008531486 A5 JP 2008531486A5

Authority

JP

Japan

Prior art keywords

alkyl

formula

alkoxy

phenyl

optionally substituted

Prior art date

2006-02-08

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.)

Granted

Links

• Espacenet
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• 150000001875 compounds Chemical class 0.000 claims 65
• 229910052736 halogen Inorganic materials 0.000 claims 49
• 150000002367 halogens Chemical class 0.000 claims 49
• 229910052739 hydrogen Inorganic materials 0.000 claims 49
• 239000001257 hydrogen Substances 0.000 claims 49
• -1 C 1 -C 6 -alkyl Chemical group 0.000 claims 48
• 239000000460 chlorine Chemical group 0.000 claims 48
• 229910052801 chlorine Inorganic materials 0.000 claims 48
• 125000004093 cyano group Chemical group *C#N 0.000 claims 44
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 43
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 40
• 229910052731 fluorine Inorganic materials 0.000 claims 39
• 239000011737 fluorine Substances 0.000 claims 39
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 34
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 34
• 229910052794 bromium Inorganic materials 0.000 claims 34
• 150000002431 hydrogen Chemical class 0.000 claims 34
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 27
• 125000001153 fluoro group Chemical group F* 0.000 claims 24
• 229910052760 oxygen Inorganic materials 0.000 claims 23
• 239000001301 oxygen Substances 0.000 claims 23
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 22
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 22
• 125000000217 alkyl group Chemical group 0.000 claims 19
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 17
• 229910052717 sulfur Inorganic materials 0.000 claims 17
• 239000011593 sulfur Substances 0.000 claims 17
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 15
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 15
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 13
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 12
• 125000003545 alkoxy group Chemical group 0.000 claims 12
• 150000003254 radicals Chemical class 0.000 claims 12
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 12
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 11
• 125000000753 cycloalkyl group Chemical group 0.000 claims 9
• 239000003085 diluting agent Substances 0.000 claims 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 9
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 8
• 125000003342 alkenyl group Chemical group 0.000 claims 8
• 125000004432 carbon atom Chemical group C* 0.000 claims 8
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 8
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 7
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 7
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 6
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 6
• 241001465754 Metazoa Species 0.000 claims 6
• 239000002253 acid Substances 0.000 claims 6
• 125000000304 alkynyl group Chemical group 0.000 claims 6
• 239000011230 binding agent Substances 0.000 claims 6
• 229910052799 carbon Inorganic materials 0.000 claims 6
• 125000002541 furyl group Chemical group 0.000 claims 6
• 125000001188 haloalkyl group Chemical group 0.000 claims 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 6
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 6
• 244000005700 microbiome Species 0.000 claims 6
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 5
• 125000001309 chloro group Chemical group Cl* 0.000 claims 5
• 244000038559 crop plants Species 0.000 claims 5
• 125000004438 haloalkoxy group Chemical group 0.000 claims 5
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
• 238000000034 method Methods 0.000 claims 5
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 5
• 125000001544 thienyl group Chemical group 0.000 claims 5
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 4
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 4
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 4
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 4
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims 4
• 125000003118 aryl group Chemical group 0.000 claims 4
• 125000001072 heteroaryl group Chemical group 0.000 claims 4
• 229910021645 metal ion Inorganic materials 0.000 claims 4
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
• 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 3
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 3
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 3
• MHULQDZDXMHODA-UHFFFAOYSA-N 1-(2,2-dichloroacetyl)-3,3,8a-trimethyl-2,4,7,8-tetrahydropyrrolo[1,2-a]pyrimidin-6-one Chemical compound C1C(C)(C)CN(C(=O)C(Cl)Cl)C2(C)N1C(=O)CC2 MHULQDZDXMHODA-UHFFFAOYSA-N 0.000 claims 3
• QWWHRELOCZEQNZ-UHFFFAOYSA-N 2,2-dichloro-1-(1-oxa-4-azaspiro[4.5]decan-4-yl)ethanone Chemical compound ClC(Cl)C(=O)N1CCOC11CCCCC1 QWWHRELOCZEQNZ-UHFFFAOYSA-N 0.000 claims 3
• VYNOULHXXDFBLU-UHFFFAOYSA-N Cumyluron Chemical compound C=1C=CC=CC=1C(C)(C)NC(=O)NCC1=CC=CC=C1Cl VYNOULHXXDFBLU-UHFFFAOYSA-N 0.000 claims 3
• 125000004414 alkyl thio group Chemical group 0.000 claims 3
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 3
• ICJSJAJWTWPSBD-UHFFFAOYSA-N cloquintocet Chemical compound C1=CN=C2C(OCC(=O)O)=CC=C(Cl)C2=C1 ICJSJAJWTWPSBD-UHFFFAOYSA-N 0.000 claims 3
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 3
• 125000005842 heteroatom Chemical group 0.000 claims 3
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
• 125000004430 oxygen atom Chemical group O* 0.000 claims 3
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims 3
• 150000003839 salts Chemical class 0.000 claims 3
• 125000001424 substituent group Chemical group 0.000 claims 3
• 125000000335 thiazolyl group Chemical group 0.000 claims 3
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 3
• 229920002554 vinyl polymer Polymers 0.000 claims 3
• 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 2
• XEJNEDVTJPXRSM-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-methyl-4,5-dihydro-1H-pyrazole-3,5-dicarboxylic acid Chemical compound OC(=O)C1(C)CC(C(O)=O)=NN1C1=CC=C(Cl)C=C1Cl XEJNEDVTJPXRSM-UHFFFAOYSA-N 0.000 claims 2
• FOMHMPJALXOZGZ-UHFFFAOYSA-N 2,2-dichloro-1-(2,2-dimethyl-1,3-oxazolidin-3-yl)ethanone Chemical compound CC1(C)OCCN1C(=O)C(Cl)Cl FOMHMPJALXOZGZ-UHFFFAOYSA-N 0.000 claims 2
• MCNOFYBITGAAGM-UHFFFAOYSA-N 2,2-dichloro-1-[5-(furan-2-yl)-2,2-dimethyl-1,3-oxazolidin-3-yl]ethanone Chemical compound C1N(C(=O)C(Cl)Cl)C(C)(C)OC1C1=CC=CO1 MCNOFYBITGAAGM-UHFFFAOYSA-N 0.000 claims 2
• YIVXMZJTEQBPQO-UHFFFAOYSA-N 2,4-DB Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1Cl YIVXMZJTEQBPQO-UHFFFAOYSA-N 0.000 claims 2
• 239000002794 2,4-DB Substances 0.000 claims 2
• 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 claims 2
• WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 claims 2
• OHXLAOJLJWLEIP-UHFFFAOYSA-N 2-(dichloromethyl)-2-methyl-1,3-dioxolane Chemical compound ClC(Cl)C1(C)OCCO1 OHXLAOJLJWLEIP-UHFFFAOYSA-N 0.000 claims 2
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 2
• 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims 2
• NNYRZQHKCHEXSD-UHFFFAOYSA-N Daimuron Chemical compound C1=CC(C)=CC=C1NC(=O)NC(C)(C)C1=CC=CC=C1 NNYRZQHKCHEXSD-UHFFFAOYSA-N 0.000 claims 2
• YRMLFORXOOIJDR-UHFFFAOYSA-N Dichlormid Chemical compound ClC(Cl)C(=O)N(CC=C)CC=C YRMLFORXOOIJDR-UHFFFAOYSA-N 0.000 claims 2
• YNQSILKYZQZHFJ-UHFFFAOYSA-N R-29148 Chemical compound CC1CN(C(=O)C(Cl)Cl)C(C)(C)O1 YNQSILKYZQZHFJ-UHFFFAOYSA-N 0.000 claims 2
• 125000003302 alkenyloxy group Chemical group 0.000 claims 2
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
• 150000005840 aryl radicals Chemical class 0.000 claims 2
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
• 238000009833 condensation Methods 0.000 claims 2
• 230000005494 condensation Effects 0.000 claims 2
• IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 claims 2
• OPGCOAPTHCZZIW-UHFFFAOYSA-N diethyl 1-(2,4-dichlorophenyl)-5-methyl-4h-pyrazole-3,5-dicarboxylate Chemical group CCOC(=O)C1(C)CC(C(=O)OCC)=NN1C1=CC=C(Cl)C=C1Cl OPGCOAPTHCZZIW-UHFFFAOYSA-N 0.000 claims 2
• LPVVTHQFIVXMEZ-UHFFFAOYSA-N diethyl 2-(5-chloroquinolin-8-yl)oxypropanedioate Chemical compound C1=CN=C2C(OC(C(=O)OCC)C(=O)OCC)=CC=C(Cl)C2=C1 LPVVTHQFIVXMEZ-UHFFFAOYSA-N 0.000 claims 2
• 125000005879 dioxolanyl group Chemical group 0.000 claims 2
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 2
• 125000000623 heterocyclic group Chemical group 0.000 claims 2
• 229910052757 nitrogen Inorganic materials 0.000 claims 2
• SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 claims 2
• 125000003386 piperidinyl group Chemical group 0.000 claims 2
• 125000004076 pyridyl group Chemical group 0.000 claims 2
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 2
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
• SODPIMGUZLOIPE-UHFFFAOYSA-N (4-chlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1 SODPIMGUZLOIPE-UHFFFAOYSA-N 0.000 claims 1
• 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 1
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
• HKELWJONQIFBPO-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-(trichloromethyl)-1,2,4-triazole-3-carboxylic acid Chemical compound N1=C(C(=O)O)N=C(C(Cl)(Cl)Cl)N1C1=CC=C(Cl)C=C1Cl HKELWJONQIFBPO-UHFFFAOYSA-N 0.000 claims 1
• MQPLQJSDTDAHBC-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-propan-2-ylpyrazole-3-carboxylic acid Chemical compound CC(C)C1=CC(C(O)=O)=NN1C1=CC=C(Cl)C=C1Cl MQPLQJSDTDAHBC-UHFFFAOYSA-N 0.000 claims 1
• UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 claims 1
• AHXUVTKVCMOKIX-UHFFFAOYSA-N 1-bromo-4-(chloromethylsulfonyl)benzene Chemical compound ClCS(=O)(=O)C1=CC=C(Br)C=C1 AHXUVTKVCMOKIX-UHFFFAOYSA-N 0.000 claims 1
• ZAWPDPLWGKAAHU-UHFFFAOYSA-N 2,2-dichloro-n-[2-oxo-2-(prop-2-enylamino)ethyl]-n-prop-2-enylacetamide Chemical compound ClC(Cl)C(=O)N(CC=C)CC(=O)NCC=C ZAWPDPLWGKAAHU-UHFFFAOYSA-N 0.000 claims 1
• HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 claims 1
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 1
• AXHCGXRBOHBEQA-UHFFFAOYSA-N 2-(5-chloro-2-methylphenoxy)acetic acid Chemical compound CC1=CC=C(Cl)C=C1OCC(O)=O AXHCGXRBOHBEQA-UHFFFAOYSA-N 0.000 claims 1
• KWGQOJWITMQEOT-UHFFFAOYSA-N 2-benzhydryloxyacetic acid Chemical compound C=1C=CC=CC=1C(OCC(=O)O)C1=CC=CC=C1 KWGQOJWITMQEOT-UHFFFAOYSA-N 0.000 claims 1
• LOHXCLHVVJGTLU-UHFFFAOYSA-N 2-oxopropyl 2-(5-chloroquinolin-8-yl)oxyacetate Chemical compound C1=CN=C2C(OCC(=O)OCC(=O)C)=CC=C(Cl)C2=C1 LOHXCLHVVJGTLU-UHFFFAOYSA-N 0.000 claims 1
• OMKXSWYZPVQWRO-UHFFFAOYSA-N 2-prop-1-enyl-1-oxa-4-azaspiro[4.5]decane-4-carbodithioic acid Chemical compound CC=CC1CN(C2(O1)CCCCC2)C(=S)S OMKXSWYZPVQWRO-UHFFFAOYSA-N 0.000 claims 1
• SIYAHZSHQIPQLY-UHFFFAOYSA-N 4-(4-chlorophenoxy)butanoic acid Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1 SIYAHZSHQIPQLY-UHFFFAOYSA-N 0.000 claims 1
• YJJIKUFGJJZYIX-UHFFFAOYSA-N 4-(5-chloro-2-methylphenyl)butanoic acid Chemical compound CC1=CC=C(Cl)C=C1CCCC(O)=O YJJIKUFGJJZYIX-UHFFFAOYSA-N 0.000 claims 1
• ZAYKVYVNMLEAMI-UHFFFAOYSA-N 4-(carboxymethyl)-2,3-dihydrochromene-4-carboxylic acid Chemical compound C1=CC=C2C(CC(=O)O)(C(O)=O)CCOC2=C1 ZAYKVYVNMLEAMI-UHFFFAOYSA-N 0.000 claims 1
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
• 125000001054 5 membered carbocyclic group Chemical group 0.000 claims 1
• CKROOYUFURJAMD-UHFFFAOYSA-N 5-tert-butyl-1-(2,4-dichlorophenyl)pyrazole Chemical compound ClC1=C(C=CC(=C1)Cl)N1N=CC=C1C(C)(C)C CKROOYUFURJAMD-UHFFFAOYSA-N 0.000 claims 1
• 125000004008 6 membered carbocyclic group Chemical group 0.000 claims 1
• PFJJMJDEVDLPNE-UHFFFAOYSA-N Benoxacor Chemical compound C1=CC=C2N(C(=O)C(Cl)Cl)C(C)COC2=C1 PFJJMJDEVDLPNE-UHFFFAOYSA-N 0.000 claims 1
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 1
• CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims 1
• 239000005504 Dicamba Substances 0.000 claims 1
• GMBRUAIJEFRHFQ-UHFFFAOYSA-N Fenchlorazole-ethyl Chemical group N1=C(C(=O)OCC)N=C(C(Cl)(Cl)Cl)N1C1=CC=C(Cl)C=C1Cl GMBRUAIJEFRHFQ-UHFFFAOYSA-N 0.000 claims 1
• NRFQZTCQAYEXEE-UHFFFAOYSA-N Fenclorim Chemical compound ClC1=CC(Cl)=NC(C=2C=CC=CC=2)=N1 NRFQZTCQAYEXEE-UHFFFAOYSA-N 0.000 claims 1
• 239000005574 MCPA Substances 0.000 claims 1
• BWPYBAJTDILQPY-UHFFFAOYSA-N Methoxyphenone Chemical compound C1=C(C)C(OC)=CC=C1C(=O)C1=CC=CC(C)=C1 BWPYBAJTDILQPY-UHFFFAOYSA-N 0.000 claims 1
• GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 claims 1
• WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 claims 1
• CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
• 239000003377 acid catalyst Substances 0.000 claims 1
• 125000005108 alkenylthio group Chemical group 0.000 claims 1
• 125000003282 alkyl amino group Chemical group 0.000 claims 1
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
• 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 1
• 150000001412 amines Chemical class 0.000 claims 1
• MKQSWTQPLLCSOB-UHFFFAOYSA-N benzyl 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate Chemical compound N1=C(Cl)SC(C(=O)OCC=2C=CC=CC=2)=C1C(F)(F)F MKQSWTQPLLCSOB-UHFFFAOYSA-N 0.000 claims 1
• 239000004067 bulking agent Substances 0.000 claims 1
• NBYQXBYMEUOBON-UHFFFAOYSA-N carbamothioyl chloride Chemical compound NC(Cl)=S NBYQXBYMEUOBON-UHFFFAOYSA-N 0.000 claims 1
• 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims 1
• 239000003054 catalyst Substances 0.000 claims 1
• FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims 1
• LRYSUGTXBIPBGB-UHFFFAOYSA-N chloromethanedithioic acid Chemical compound SC(Cl)=S LRYSUGTXBIPBGB-UHFFFAOYSA-N 0.000 claims 1
• KTRFZWJCHOQHMN-UHFFFAOYSA-N chloromethanethioic s-acid Chemical compound SC(Cl)=O KTRFZWJCHOQHMN-UHFFFAOYSA-N 0.000 claims 1
• 125000005366 cycloalkylthio group Chemical group 0.000 claims 1
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
• 230000018044 dehydration Effects 0.000 claims 1
• 238000006297 dehydration reaction Methods 0.000 claims 1
• 125000004663 dialkyl amino group Chemical group 0.000 claims 1
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
• 150000002009 diols Chemical class 0.000 claims 1
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 1
• JEMXUSHXYOXNFL-UHFFFAOYSA-N ethyl 2-(5-chloroquinolin-8-yl)oxyacetate Chemical compound C1=CN=C2C(OCC(=O)OCC)=CC=C(Cl)C2=C1 JEMXUSHXYOXNFL-UHFFFAOYSA-N 0.000 claims 1
• VZZVOKHLRXJIEP-UHFFFAOYSA-N ethyl 2-benzhydryloxyacetate Chemical compound C=1C=CC=CC=1C(OCC(=O)OCC)C1=CC=CC=C1 VZZVOKHLRXJIEP-UHFFFAOYSA-N 0.000 claims 1
• ZKDUJUNNBWZZCO-UHFFFAOYSA-N ethyl 5-[(2,4-dichlorophenyl)methyl]-4,5-dihydro-1,2-oxazole-3-carboxylate Chemical compound C1C(C(=O)OCC)=NOC1CC1=CC=C(Cl)C=C1Cl ZKDUJUNNBWZZCO-UHFFFAOYSA-N 0.000 claims 1
• YNZGZAJXHXGDBF-UHFFFAOYSA-N ethyl 5-phenyl-4,5-dihydro-1,2-oxazole-3-carboxylate Chemical compound C1C(C(=O)OCC)=NOC1C1=CC=CC=C1 YNZGZAJXHXGDBF-UHFFFAOYSA-N 0.000 claims 1
• 125000005291 haloalkenyloxy group Chemical group 0.000 claims 1
• 125000001475 halogen functional group Chemical group 0.000 claims 1
• COYBRKAVBMYYSF-UHFFFAOYSA-N heptan-2-yl [(5-chloroquinolin-8-yl)oxy]acetate Chemical compound C1=CN=C2C(OCC(=O)OC(C)CCCCC)=CC=C(Cl)C2=C1 COYBRKAVBMYYSF-UHFFFAOYSA-N 0.000 claims 1
• 239000004615 ingredient Substances 0.000 claims 1
• 239000012948 isocyanate Substances 0.000 claims 1
• 150000002513 isocyanates Chemical class 0.000 claims 1
• 150000002540 isothiocyanates Chemical class 0.000 claims 1
• MWKVXOJATACCCH-UHFFFAOYSA-N isoxadifen-ethyl Chemical group C1C(C(=O)OCC)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 MWKVXOJATACCCH-UHFFFAOYSA-N 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• 239000002184 metal Substances 0.000 claims 1
• 150000002736 metal compounds Chemical class 0.000 claims 1
• JCHMGYRXQDASJE-UHFFFAOYSA-N metcamifen Chemical compound C1=CC(NC(=O)NC)=CC=C1S(=O)(=O)NC(=O)C1=CC=CC=C1OC JCHMGYRXQDASJE-UHFFFAOYSA-N 0.000 claims 1
• DLCGDGOEOISSHF-UHFFFAOYSA-N methyl 1-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylate Chemical compound C=1C=CC=C(Cl)C=1N1N=C(C(=O)OC)C=C1C1=CC=CC=C1 DLCGDGOEOISSHF-UHFFFAOYSA-N 0.000 claims 1
• DSLIOOISXCVKML-UHFFFAOYSA-N methyl 2-(8-chloroquinoxalin-5-yl)oxyacetate Chemical compound C1=CN=C2C(OCC(=O)OC)=CC=C(Cl)C2=N1 DSLIOOISXCVKML-UHFFFAOYSA-N 0.000 claims 1
• LQPRNRFJJUSONA-UHFFFAOYSA-N methyl 2-benzhydryloxyacetate Chemical compound C=1C=CC=CC=1C(OCC(=O)OC)C1=CC=CC=C1 LQPRNRFJJUSONA-UHFFFAOYSA-N 0.000 claims 1
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims 1
• WFVUIONFJOAYPK-UHFFFAOYSA-N n-(1,3-dioxolan-2-ylmethoxy)benzenecarboximidoyl cyanide Chemical compound C=1C=CC=CC=1C(C#N)=NOCC1OCCO1 WFVUIONFJOAYPK-UHFFFAOYSA-N 0.000 claims 1
• NYDKNJDNBUFWRJ-UHFFFAOYSA-N n-[4-(dimethylcarbamoylamino)phenyl]sulfonyl-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)NS(=O)(=O)C1=CC=C(NC(=O)N(C)C)C=C1 NYDKNJDNBUFWRJ-UHFFFAOYSA-N 0.000 claims 1
• 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
• 125000005359 phenoxyalkyl group Chemical group 0.000 claims 1
• 125000003884 phenylalkyl group Chemical group 0.000 claims 1
• 229910052698 phosphorus Inorganic materials 0.000 claims 1
• 239000011574 phosphorus Substances 0.000 claims 1
• 238000002360 preparation method Methods 0.000 claims 1
• 125000003226 pyrazolyl group Chemical group 0.000 claims 1
• 125000005554 pyridyloxy group Chemical group 0.000 claims 1
• 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
• 125000003107 substituted aryl group Chemical group 0.000 claims 1
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
• 125000004434 sulfur atom Chemical group 0.000 claims 1
• 125000004354 sulfur functional group Chemical group 0.000 claims 1
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims 1
• 239000004094 surface-active agent Substances 0.000 claims 1
• 0 CC(CCC(C1)(C(ON)=C2c3c(*)cc(C)c(N)c3*)OC2=O)(C*(*)CC1(C)N)N Chemical compound CC(CCC(C1)(C(ON)=C2c3c(*)cc(C)c(N)c3*)OC2=O)(C*(*)CC1(C)N)N 0.000 description 3