BRPI0607807B1 - cetoenóis cíclicos substituídos por espirocetal, seu processo de produção, seus usos e seus intermediários, agentes e seu processo de produção, processos para combate de parasitas, do crescimento indesejado de plantas e/ou de microorganismos indesejados - Google Patents

Info

Publication number

BRPI0607807B1

BRPI0607807B1 BRPI0607807A BRPI0607807A BRPI0607807B1 BR PI0607807 B1 BRPI0607807 B1 BR PI0607807B1 BR PI0607807 A BRPI0607807 A BR PI0607807A BR PI0607807 A BRPI0607807 A BR PI0607807A BR PI0607807 B1 BRPI0607807 B1 BR PI0607807B1

Authority

BR

Brazil

Prior art keywords

compounds

alkyl

formula

acid

spp

Prior art date

2005-02-22

Links

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• 238000000034 method Methods 0.000 title claims abstract description 98
• 230000008569 process Effects 0.000 title claims abstract description 76
• 238000004519 manufacturing process Methods 0.000 title claims abstract description 11
• 244000005700 microbiome Species 0.000 title claims description 17
• 230000008635 plant growth Effects 0.000 title claims description 11
• 244000045947 parasite Species 0.000 title claims description 10
• 125000004122 cyclic group Chemical class 0.000 title abstract description 8
• 239000000543 intermediate Substances 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 224
• -1 chloroformic acid thioesters Chemical class 0.000 claims description 224
• 239000013543 active substance Substances 0.000 claims description 140
• 239000000460 chlorine Substances 0.000 claims description 79
• 229910052801 chlorine Inorganic materials 0.000 claims description 79
• 125000000217 alkyl group Chemical group 0.000 claims description 75
• 239000001257 hydrogen Substances 0.000 claims description 74
• 229910052739 hydrogen Inorganic materials 0.000 claims description 74
• 229910052736 halogen Inorganic materials 0.000 claims description 70
• 150000002367 halogens Chemical class 0.000 claims description 65
• 239000003085 diluting agent Substances 0.000 claims description 63
• 150000002431 hydrogen Chemical class 0.000 claims description 63
• 239000002253 acid Substances 0.000 claims description 62
• 125000003545 alkoxy group Chemical group 0.000 claims description 62
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 58
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 58
• 229910052794 bromium Inorganic materials 0.000 claims description 58
• 229910052731 fluorine Inorganic materials 0.000 claims description 57
• 239000011737 fluorine Substances 0.000 claims description 57
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 57
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 53
• 239000000126 substance Substances 0.000 claims description 43
• 239000003795 chemical substances by application Substances 0.000 claims description 36
• 239000011230 binding agent Substances 0.000 claims description 29
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 28
• 229910052760 oxygen Inorganic materials 0.000 claims description 24
• 239000001301 oxygen Substances 0.000 claims description 24
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 22
• 229910052717 sulfur Inorganic materials 0.000 claims description 22
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 21
• 125000001153 fluoro group Chemical group F* 0.000 claims description 21
• 239000011593 sulfur Substances 0.000 claims description 21
• 125000001188 haloalkyl group Chemical group 0.000 claims description 20
• 150000002148 esters Chemical class 0.000 claims description 18
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 17
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 17
• 125000001424 substituent group Chemical group 0.000 claims description 16
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 13
• 150000003839 salts Chemical class 0.000 claims description 13
• 125000003342 alkenyl group Chemical group 0.000 claims description 12
• 125000002541 furyl group Chemical group 0.000 claims description 12
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 11
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
• 229910052751 metal Inorganic materials 0.000 claims description 11
• 239000002184 metal Substances 0.000 claims description 11
• 241001465754 Metazoa Species 0.000 claims description 10
• 238000002156 mixing Methods 0.000 claims description 10
• 229910052799 carbon Inorganic materials 0.000 claims description 9
• 230000002708 enhancing effect Effects 0.000 claims description 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
• 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 8
• 125000001544 thienyl group Chemical group 0.000 claims description 8
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 7
• 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 description 7
• 239000003054 catalyst Substances 0.000 claims description 7
• 125000000335 thiazolyl group Chemical group 0.000 claims description 7
• 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 description 6
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
• 244000000054 animal parasite Species 0.000 claims description 6
• 229910052796 boron Inorganic materials 0.000 claims description 6
• 125000004494 ethyl ester group Chemical group 0.000 claims description 6
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
• 125000003386 piperidinyl group Chemical group 0.000 claims description 6
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
• 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 claims description 5
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 5
• 125000000304 alkynyl group Chemical group 0.000 claims description 5
• BWUPSGJXXPATLU-UHFFFAOYSA-N dimepiperate Chemical compound C=1C=CC=CC=1C(C)(C)SC(=O)N1CCCCC1 BWUPSGJXXPATLU-UHFFFAOYSA-N 0.000 claims description 5
• 150000002009 diols Chemical class 0.000 claims description 5
• 230000012010 growth Effects 0.000 claims description 5
• MWKVXOJATACCCH-UHFFFAOYSA-N isoxadifen-ethyl Chemical compound C1C(C(=O)OCC)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 MWKVXOJATACCCH-UHFFFAOYSA-N 0.000 claims description 5
• 229910052721 tungsten Inorganic materials 0.000 claims description 5
• 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 description 4
• 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 description 4
• YIVXMZJTEQBPQO-UHFFFAOYSA-N 2,4-DB Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1Cl YIVXMZJTEQBPQO-UHFFFAOYSA-N 0.000 claims description 4
• 239000002794 2,4-DB Substances 0.000 claims description 4
• 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 description 4
• OHXLAOJLJWLEIP-UHFFFAOYSA-N 2-(dichloromethyl)-2-methyl-1,3-dioxolane Chemical compound ClC(Cl)C1(C)OCCO1 OHXLAOJLJWLEIP-UHFFFAOYSA-N 0.000 claims description 4
• PFJJMJDEVDLPNE-UHFFFAOYSA-N Benoxacor Chemical compound C1=CC=C2N(C(=O)C(Cl)Cl)C(C)COC2=C1 PFJJMJDEVDLPNE-UHFFFAOYSA-N 0.000 claims description 4
• 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 description 4
• YRMLFORXOOIJDR-UHFFFAOYSA-N Dichlormid Chemical compound ClC(Cl)C(=O)N(CC=C)CC=C YRMLFORXOOIJDR-UHFFFAOYSA-N 0.000 claims description 4
• NRFQZTCQAYEXEE-UHFFFAOYSA-N Fenclorim Chemical compound ClC1=CC(Cl)=NC(C=2C=CC=CC=2)=N1 NRFQZTCQAYEXEE-UHFFFAOYSA-N 0.000 claims description 4
• YNQSILKYZQZHFJ-UHFFFAOYSA-N R-29148 Chemical compound CC1CN(C(=O)C(Cl)Cl)C(C)(C)O1 YNQSILKYZQZHFJ-UHFFFAOYSA-N 0.000 claims description 4
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
• 125000004432 carbon atom Chemical group C* 0.000 claims description 4
• 125000000623 heterocyclic group Chemical group 0.000 claims description 4
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
• 239000012948 isocyanate Substances 0.000 claims description 4
• 150000002513 isocyanates Chemical class 0.000 claims description 4
• 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 description 4
• 150000003018 phosphorus compounds Chemical class 0.000 claims description 4
• CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 3
• 239000005504 Dicamba Substances 0.000 claims description 3
• 239000005574 MCPA Substances 0.000 claims description 3
• WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 claims description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 3
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
• IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 claims description 3
• OPGCOAPTHCZZIW-UHFFFAOYSA-N diethyl 1-(2,4-dichlorophenyl)-5-methyl-4h-pyrazole-3,5-dicarboxylate Chemical compound CCOC(=O)C1(C)CC(C(=O)OCC)=NN1C1=CC=C(Cl)C=C1Cl OPGCOAPTHCZZIW-UHFFFAOYSA-N 0.000 claims description 3
• SODPIMGUZLOIPE-UHFFFAOYSA-N (4-chlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1 SODPIMGUZLOIPE-UHFFFAOYSA-N 0.000 claims description 2
• VXJKYWLPNZBSMY-UHFFFAOYSA-N 1,1-dimethyl-3-[4-(naphthalen-1-ylsulfamoyl)phenyl]urea Chemical compound C1=CC(NC(=O)N(C)C)=CC=C1S(=O)(=O)NC1=CC=CC2=CC=CC=C12 VXJKYWLPNZBSMY-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 claims description 2
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 2
• MALIONKMKPITBV-UHFFFAOYSA-N 2-(3-chloro-4-hydroxyphenyl)-n-[2-(4-sulfamoylphenyl)ethyl]acetamide Chemical group C1=CC(S(=O)(=O)N)=CC=C1CCNC(=O)CC1=CC=C(O)C(Cl)=C1 MALIONKMKPITBV-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• SIYAHZSHQIPQLY-UHFFFAOYSA-N 4-(4-chlorophenoxy)butanoic acid Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1 SIYAHZSHQIPQLY-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 239000005711 Benzoic acid Substances 0.000 claims description 2
• PYKLUAIDKVVEOS-UHFFFAOYSA-N Cyometrinil Chemical compound N#CCON=C(C#N)C1=CC=CC=C1 PYKLUAIDKVVEOS-UHFFFAOYSA-N 0.000 claims description 2
• 239000003377 acid catalyst Substances 0.000 claims description 2
• 235000010233 benzoic acid Nutrition 0.000 claims description 2
• NBYQXBYMEUOBON-UHFFFAOYSA-N carbamothioyl chloride Chemical class NC(Cl)=S NBYQXBYMEUOBON-UHFFFAOYSA-N 0.000 claims description 2
• AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 claims description 2
• 125000005366 cycloalkylthio group Chemical group 0.000 claims description 2
• 125000005879 dioxolanyl group Chemical group 0.000 claims description 2
• 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 description 2
• 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 description 2
• 150000002540 isothiocyanates Chemical class 0.000 claims description 2
• 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 description 2
• HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 claims description 2
• 230000003071 parasitic effect Effects 0.000 claims description 2
• PIFBBBPNSVFJHQ-UHFFFAOYSA-N phenyl 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate Chemical compound N1=C(Cl)SC(C(=O)OC=2C=CC=CC=2)=C1C(F)(F)F PIFBBBPNSVFJHQ-UHFFFAOYSA-N 0.000 claims description 2
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 6
• 238000001356 surgical procedure Methods 0.000 claims 2
• 230000001225 therapeutic effect Effects 0.000 claims 2
• 125000000229 (C1-C4)alkoxy 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
• JTBBWRKSUYCPFY-UHFFFAOYSA-N 2,3-dihydro-1h-pyrimidin-4-one Chemical compound O=C1NCNC=C1 JTBBWRKSUYCPFY-UHFFFAOYSA-N 0.000 claims 1
• 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
• APSJLVHJSVHYQZ-UHFFFAOYSA-N 4,5-diphenyl-4,5-dihydro-1,2-oxazole-3-carboxylic acid Chemical compound OC(=O)C1=NOC(C1C1=CC=CC=C1)C1=CC=CC=C1 APSJLVHJSVHYQZ-UHFFFAOYSA-N 0.000 claims 1
• NOBPWDYRGXWVRL-UHFFFAOYSA-N 5-[(2,4-dichlorophenyl)methyl]-4,5-dihydro-1,2-oxazole-3-carboxylic acid Chemical compound C1C(C(=O)O)=NOC1CC1=CC=C(Cl)C=C1Cl NOBPWDYRGXWVRL-UHFFFAOYSA-N 0.000 claims 1
• CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims 1
• IVCSFRPEOSTNTK-UHFFFAOYSA-N C1(=CC=CC=C1)C1=N[ClH]C=C1 Chemical compound C1(=CC=CC=C1)C1=N[ClH]C=C1 IVCSFRPEOSTNTK-UHFFFAOYSA-N 0.000 claims 1
• MIJDWRFNRZSSHX-UHFFFAOYSA-N CON=C(C#N)C1=CC=CC=C1C2OCCO2 Chemical compound CON=C(C#N)C1=CC=CC=C1C2OCCO2 MIJDWRFNRZSSHX-UHFFFAOYSA-N 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
• XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 claims 1
• 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims 1
• 125000004453 alkoxycarbonyl group Chemical group 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
• 239000004202 carbamide Substances 0.000 claims 1
• 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims 1
• 239000003623 enhancer Substances 0.000 claims 1
• IVEMKPKJNOWXSK-UHFFFAOYSA-N ethyl 1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate Chemical compound N1=C(C(=O)OCC)C=C(C)N1C1=CC=C(Cl)C=C1Cl IVEMKPKJNOWXSK-UHFFFAOYSA-N 0.000 claims 1
• COYBRKAVBMYYSF-UHFFFAOYSA-N heptan-2-yl [(5-chloroquinolin-8-yl)oxy]acetate Chemical group C1=CN=C2C(OCC(=O)OC(C)CCCCC)=CC=C(Cl)C2=C1 COYBRKAVBMYYSF-UHFFFAOYSA-N 0.000 claims 1
• RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 claims 1
• 150000004702 methyl esters Chemical class 0.000 claims 1
• CMCJQHLLWDPWPK-UHFFFAOYSA-N n-[4-(cyclopropylcarbamoyl)phenyl]sulfonyl-2-methoxy-5-methylbenzamide Chemical compound COC1=CC=C(C)C=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NC2CC2)C=C1 CMCJQHLLWDPWPK-UHFFFAOYSA-N 0.000 claims 1
• JSJMNJUBFHFEAS-UHFFFAOYSA-N n-[4-(dimethylcarbamoylamino)phenyl]sulfonyl-n-methoxybenzamide Chemical compound C=1C=C(NC(=O)N(C)C)C=CC=1S(=O)(=O)N(OC)C(=O)C1=CC=CC=C1 JSJMNJUBFHFEAS-UHFFFAOYSA-N 0.000 claims 1
• 230000002123 temporal effect Effects 0.000 claims 1
• 239000000203 mixture Substances 0.000 abstract description 58
• 230000002363 herbicidal effect Effects 0.000 abstract description 25
• 239000004009 herbicide Substances 0.000 abstract description 24
• 230000003641 microbiacidal effect Effects 0.000 abstract description 4
• 229940124561 microbicide Drugs 0.000 abstract description 3
• 239000000575 pesticide Substances 0.000 abstract description 3
• 239000002855 microbicide agent Substances 0.000 abstract description 2
• 241000196324 Embryophyta Species 0.000 description 109
• YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 94
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 73
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 72
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 57
• 239000002904 solvent Substances 0.000 description 55
• 238000002360 preparation method Methods 0.000 description 49
• 238000006243 chemical reaction Methods 0.000 description 43
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 43
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 37
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 32
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