TWI713530B - 作為除草劑之嘧啶氧基苯衍生物 - Google Patents

Info

Publication number

TWI713530B

TWI713530B TW105116619A TW105116619A TWI713530B TW I713530 B TWI713530 B TW I713530B TW 105116619 A TW105116619 A TW 105116619A TW 105116619 A TW105116619 A TW 105116619A TW I713530 B TWI713530 B TW I713530B

Authority

TW

Taiwan

Prior art keywords

compound

alkyl

haloalkyl

group

alkoxy

Prior art date

2015-06-05

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• 239000004009 herbicide Substances 0.000 title claims description 49
• CEBDRQUBQYQBEV-UHFFFAOYSA-N 2-phenoxypyrimidine Chemical class N=1C=CC=NC=1OC1=CC=CC=C1 CEBDRQUBQYQBEV-UHFFFAOYSA-N 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 394
• 239000000203 mixture Substances 0.000 claims abstract description 100
• 238000000034 method Methods 0.000 claims abstract description 41
• 150000003839 salts Chemical class 0.000 claims abstract description 33
• 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 description 172
• -1 C 1 -C 6 nitroalkyl Chemical group 0.000 claims description 139
• 229910052736 halogen Inorganic materials 0.000 claims description 64
• 150000002367 halogens Chemical class 0.000 claims description 64
• 239000003112 inhibitor Substances 0.000 claims description 61
• 230000002363 herbicidal effect Effects 0.000 claims description 54
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 47
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 45
• 125000000217 alkyl group Chemical group 0.000 claims description 35
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 31
• 239000004480 active ingredient Substances 0.000 claims description 31
• 229910052739 hydrogen Inorganic materials 0.000 claims description 31
• 239000003085 diluting agent Substances 0.000 claims description 27
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 26
• 229910052799 carbon Inorganic materials 0.000 claims description 26
• 239000007788 liquid Substances 0.000 claims description 25
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 24
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 23
• 239000007787 solid Substances 0.000 claims description 23
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 22
• 239000004094 surface-active agent Substances 0.000 claims description 22
• 230000015572 biosynthetic process Effects 0.000 claims description 19
• 238000003786 synthesis reaction Methods 0.000 claims description 19
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 18
• 239000002253 acid Substances 0.000 claims description 18
• 239000003795 chemical substances by application Substances 0.000 claims description 18
• 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 17
• 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 16
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 15
• 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 14
• SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 claims description 14
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 13
• 230000012010 growth Effects 0.000 claims description 13
• 108010068327 4-hydroxyphenylpyruvate dioxygenase Proteins 0.000 claims description 12
• 102100028626 4-hydroxyphenylpyruvate dioxygenase Human genes 0.000 claims description 12
• 229930192334 Auxin Natural products 0.000 claims description 12
• 239000002363 auxin Substances 0.000 claims description 12
• 229910052760 oxygen Inorganic materials 0.000 claims description 12
• 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 11
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 11
• 150000004669 very long chain fatty acids Chemical class 0.000 claims description 11
• 239000005562 Glyphosate Substances 0.000 claims description 10
• 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 10
• 229910052717 sulfur Inorganic materials 0.000 claims description 10
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 9
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 9
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 9
• 102000000452 Acetyl-CoA carboxylase Human genes 0.000 claims description 9
• 108010016219 Acetyl-CoA carboxylase Proteins 0.000 claims description 9
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 9
• OTSAMNSACVKIOJ-UHFFFAOYSA-N azane;carbamoyl(ethoxy)phosphinic acid Chemical compound [NH4+].CCOP([O-])(=O)C(N)=O OTSAMNSACVKIOJ-UHFFFAOYSA-N 0.000 claims description 9
• 229910052731 fluorine Inorganic materials 0.000 claims description 9
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 9
• 125000006798 (C1-C6) haloalkylamino group Chemical group 0.000 claims description 8
• 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 8
• 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 claims description 8
• QUTYKIXIUDQOLK-PRJMDXOYSA-N 5-O-(1-carboxyvinyl)-3-phosphoshikimic acid Chemical compound O[C@H]1[C@H](OC(=C)C(O)=O)CC(C(O)=O)=C[C@H]1OP(O)(O)=O QUTYKIXIUDQOLK-PRJMDXOYSA-N 0.000 claims description 8
• 125000005366 cycloalkylthio group Chemical group 0.000 claims description 8
• XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims description 8
• 229940097068 glyphosate Drugs 0.000 claims description 8
• QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 8
• FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims description 8
• 239000005504 Dicamba Substances 0.000 claims description 7
• 108010060806 Photosystem II Protein Complex Proteins 0.000 claims description 7
• 239000005616 Rimsulfuron Substances 0.000 claims description 7
• IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 claims description 7
• 108010001545 phytoene dehydrogenase Proteins 0.000 claims description 7
• MEFOUWRMVYJCQC-UHFFFAOYSA-N rimsulfuron Chemical compound CCS(=O)(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 MEFOUWRMVYJCQC-UHFFFAOYSA-N 0.000 claims description 7
• IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 claims description 6
• UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 claims description 6
• 239000005489 Bromoxynil Substances 0.000 claims description 6
• 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 description 6
• 239000005529 Florasulam Substances 0.000 claims description 6
• QZXATCCPQKOEIH-UHFFFAOYSA-N Florasulam Chemical compound N=1N2C(OC)=NC=C(F)C2=NC=1S(=O)(=O)NC1=C(F)C=CC=C1F QZXATCCPQKOEIH-UHFFFAOYSA-N 0.000 claims description 6
• 239000005578 Mesotrione Substances 0.000 claims description 6
• MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 claims description 6
• ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 claims description 6
• 150000002576 ketones Chemical class 0.000 claims description 6
• KPUREKXXPHOJQT-UHFFFAOYSA-N mesotrione Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O KPUREKXXPHOJQT-UHFFFAOYSA-N 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• GNHDVXLWBQYPJE-UHFFFAOYSA-N saflufenacil Chemical compound C1=C(Cl)C(C(=O)NS(=O)(=O)N(C)C(C)C)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F GNHDVXLWBQYPJE-UHFFFAOYSA-N 0.000 claims description 6
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
• GBUQDHNLEZWHOS-UHFFFAOYSA-N 3,3,3-trifluoropropyl 2-bromo-6-(5-chloropyrimidin-2-yl)oxybenzoate Chemical compound BrC1=C(C(=O)OCCC(F)(F)F)C(=CC=C1)OC1=NC=C(C=N1)Cl GBUQDHNLEZWHOS-UHFFFAOYSA-N 0.000 claims description 5
• 239000005492 Carfentrazone-ethyl Substances 0.000 claims description 5
• 239000005531 Flufenacet Substances 0.000 claims description 5
• FCOHEOSCARXMMS-UHFFFAOYSA-N Oxaziclomefone Chemical compound C1OC(C)=C(C=2C=CC=CC=2)C(=O)N1C(C)(C)C1=CC(Cl)=CC(Cl)=C1 FCOHEOSCARXMMS-UHFFFAOYSA-N 0.000 claims description 5
• 108090000854 Oxidoreductases Proteins 0.000 claims description 5
• 102000004316 Oxidoreductases Human genes 0.000 claims description 5
• XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 claims description 5
• VGPYEHKOIGNJKV-UHFFFAOYSA-N asulam Chemical compound COC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 VGPYEHKOIGNJKV-UHFFFAOYSA-N 0.000 claims description 5
• 230000008166 cellulose biosynthesis Effects 0.000 claims description 5
• BIKACRYIQSLICJ-UHFFFAOYSA-N cloransulam-methyl Chemical group N=1N2C(OCC)=NC(F)=CC2=NC=1S(=O)(=O)NC1=C(Cl)C=CC=C1C(=O)OC BIKACRYIQSLICJ-UHFFFAOYSA-N 0.000 claims description 5
• MLKCGVHIFJBRCD-UHFFFAOYSA-N ethyl 2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-4-fluorophenyl}propanoate Chemical group C1=C(Cl)C(CC(Cl)C(=O)OCC)=CC(N2C(N(C(F)F)C(C)=N2)=O)=C1F MLKCGVHIFJBRCD-UHFFFAOYSA-N 0.000 claims description 5
• QMTNOLKHSWIQBE-FGTMMUONSA-N exo-(+)-cinmethylin Chemical compound O([C@H]1[C@]2(C)CC[C@@](O2)(C1)C(C)C)CC1=CC=CC=C1C QMTNOLKHSWIQBE-FGTMMUONSA-N 0.000 claims description 5
• IANUJLZYFUDJIH-UHFFFAOYSA-N flufenacet Chemical compound C=1C=C(F)C=CC=1N(C(C)C)C(=O)COC1=NN=C(C(F)(F)F)S1 IANUJLZYFUDJIH-UHFFFAOYSA-N 0.000 claims description 5
• FOUWCSDKDDHKQP-UHFFFAOYSA-N flumioxazin Chemical compound FC1=CC=2OCC(=O)N(CC#C)C=2C=C1N(C1=O)C(=O)C2=C1CCCC2 FOUWCSDKDDHKQP-UHFFFAOYSA-N 0.000 claims description 5
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
• WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 claims description 4
• CASLETQIYIQFTQ-UHFFFAOYSA-N 3-[[5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)pyrazol-4-yl]methylsulfonyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound CN1N=C(C(F)(F)F)C(CS(=O)(=O)C=2CC(C)(C)ON=2)=C1OC(F)F CASLETQIYIQFTQ-UHFFFAOYSA-N 0.000 claims description 4
• VTNQPKFIQCLBDU-UHFFFAOYSA-N Acetochlor Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1CC VTNQPKFIQCLBDU-UHFFFAOYSA-N 0.000 claims description 4
• 239000005644 Dazomet Substances 0.000 claims description 4
• 239000005509 Dimethenamid-P Substances 0.000 claims description 4
• ICWUMLXQKFTJMH-UHFFFAOYSA-N Etobenzanid Chemical compound C1=CC(OCOCC)=CC=C1C(=O)NC1=CC=CC(Cl)=C1Cl ICWUMLXQKFTJMH-UHFFFAOYSA-N 0.000 claims description 4
• 239000005534 Flupyrsulfuron-methyl Substances 0.000 claims description 4
• GXAMYUGOODKVRM-UHFFFAOYSA-N Flurecol Chemical compound C1=CC=C2C(C(=O)O)(O)C3=CC=CC=C3C2=C1 GXAMYUGOODKVRM-UHFFFAOYSA-N 0.000 claims description 4
• 239000005563 Halauxifen-methyl Substances 0.000 claims description 4
• 239000005571 Isoxaflutole Substances 0.000 claims description 4
• 239000005574 MCPA Substances 0.000 claims description 4
• 239000002169 Metam Substances 0.000 claims description 4
• FMINYZXVCTYSNY-UHFFFAOYSA-N Methyldymron Chemical compound C=1C=CC=CC=1N(C)C(=O)NC(C)(C)C1=CC=CC=C1 FMINYZXVCTYSNY-UHFFFAOYSA-N 0.000 claims description 4
• 239000005584 Metsulfuron-methyl Substances 0.000 claims description 4
• 239000005586 Nicosulfuron Substances 0.000 claims description 4
• 239000005643 Pelargonic acid Substances 0.000 claims description 4
• 108010081996 Photosystem I Protein Complex Proteins 0.000 claims description 4
• 239000005607 Pyroxsulam Substances 0.000 claims description 4
• 239000005620 Tembotrione Substances 0.000 claims description 4
• 239000005623 Thifensulfuron-methyl Substances 0.000 claims description 4
• WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 claims description 4
• WZDDLAZXUYIVMU-UHFFFAOYSA-N bromobutide Chemical compound CC(C)(C)C(Br)C(=O)NC(C)(C)C1=CC=CC=C1 WZDDLAZXUYIVMU-UHFFFAOYSA-N 0.000 claims description 4
• NPZYKQZYWNQMDV-UHFFFAOYSA-N but-3-enyl 2-bromo-6-(5-chloropyrimidin-2-yl)oxybenzoate Chemical compound BrC1=C(C(=O)OCCC=C)C(=CC=C1)OC1=NC=C(C=N1)Cl NPZYKQZYWNQMDV-UHFFFAOYSA-N 0.000 claims description 4
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 4
• QAYICIQNSGETAS-UHFFFAOYSA-N dazomet Chemical compound CN1CSC(=S)N(C)C1 QAYICIQNSGETAS-UHFFFAOYSA-N 0.000 claims description 4
• JLYFCTQDENRSOL-VIFPVBQESA-N dimethenamid-P Chemical compound COC[C@H](C)N(C(=O)CCl)C=1C(C)=CSC=1C JLYFCTQDENRSOL-VIFPVBQESA-N 0.000 claims description 4
• KDHKOPYYWOHESS-UHFFFAOYSA-N halauxifen-methyl Chemical group NC1=C(Cl)C(C(=O)OC)=NC(C=2C(=C(OC)C(Cl)=CC=2)F)=C1 KDHKOPYYWOHESS-UHFFFAOYSA-N 0.000 claims description 4
• OYIKARCXOQLFHF-UHFFFAOYSA-N isoxaflutole Chemical compound CS(=O)(=O)C1=CC(C(F)(F)F)=CC=C1C(=O)C1=C(C2CC2)ON=C1 OYIKARCXOQLFHF-UHFFFAOYSA-N 0.000 claims description 4
• 229940088649 isoxaflutole Drugs 0.000 claims description 4
• DTVOKYWXACGVGO-UHFFFAOYSA-N methyl 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-6-(trifluoromethyl)pyridine-3-carboxylate Chemical group COC(=O)C1=CC=C(C(F)(F)F)N=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 DTVOKYWXACGVGO-UHFFFAOYSA-N 0.000 claims description 4
• 229940095102 methyl benzoate Drugs 0.000 claims description 4
• RSMUVYRMZCOLBH-UHFFFAOYSA-N metsulfuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 RSMUVYRMZCOLBH-UHFFFAOYSA-N 0.000 claims description 4
• 230000003278 mimic effect Effects 0.000 claims description 4
• GLBLPMUBLHYFCW-UHFFFAOYSA-N n-(5,7-dimethoxy-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-2-methoxy-4-(trifluoromethyl)pyridine-3-sulfonamide Chemical compound N1=C2N=C(OC)C=C(OC)N2N=C1NS(=O)(=O)C1=C(OC)N=CC=C1C(F)(F)F GLBLPMUBLHYFCW-UHFFFAOYSA-N 0.000 claims description 4
• RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 claims description 4
• DWSPRBSLSXQIEJ-UHFFFAOYSA-N pyrasulfotole Chemical compound CC1=NN(C)C(O)=C1C(=O)C1=CC=C(C(F)(F)F)C=C1S(C)(=O)=O DWSPRBSLSXQIEJ-UHFFFAOYSA-N 0.000 claims description 4
• VTRWMTJQBQJKQH-UHFFFAOYSA-N pyributicarb Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C=CC=2)C(C)(C)C)=N1 VTRWMTJQBQJKQH-UHFFFAOYSA-N 0.000 claims description 4
• IUQAXCIUEPFPSF-UHFFFAOYSA-N tembotrione Chemical compound ClC1=C(COCC(F)(F)F)C(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O IUQAXCIUEPFPSF-UHFFFAOYSA-N 0.000 claims description 4
• AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 claims description 4
• RFZZKBWDDKMWNM-GTBMBKLPSA-N (5s,7r,8s,9r)-8,9-dihydroxy-7-(hydroxymethyl)-6-oxa-1,3-diazaspiro[4.4]nonane-2,4-dione Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@]11C(=O)NC(=O)N1 RFZZKBWDDKMWNM-GTBMBKLPSA-N 0.000 claims description 3
• OMTXNHCOMNRAJT-UHFFFAOYSA-N 3,3,3-trifluoropropyl 2-chloro-6-(5-chloropyrimidin-2-yl)oxybenzoate Chemical compound ClC1=C(C(=O)OCCC(F)(F)F)C(=CC=C1)OC1=NC=C(C=N1)Cl OMTXNHCOMNRAJT-UHFFFAOYSA-N 0.000 claims description 3
• LBGPXIPGGRQBJW-UHFFFAOYSA-N Difenzoquat Chemical compound C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 LBGPXIPGGRQBJW-UHFFFAOYSA-N 0.000 claims description 3
• 229940106987 Elongase inhibitor Drugs 0.000 claims description 3
• RFZZKBWDDKMWNM-UHFFFAOYSA-N Hydantocidin Natural products OC1C(O)C(CO)OC11C(=O)NC(=O)N1 RFZZKBWDDKMWNM-UHFFFAOYSA-N 0.000 claims description 3
• 229910052785 arsenic Inorganic materials 0.000 claims description 3
• RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 3
• UDEWPOVQBGFNGE-UHFFFAOYSA-N benzoic acid n-propyl ester Natural products CCCOC(=O)C1=CC=CC=C1 UDEWPOVQBGFNGE-UHFFFAOYSA-N 0.000 claims description 3
• 239000011737 fluorine Substances 0.000 claims description 3
• HYVVJDQGXFXBRZ-UHFFFAOYSA-N metam Chemical compound CNC(S)=S HYVVJDQGXFXBRZ-UHFFFAOYSA-N 0.000 claims description 3
• OLXYLDUSSBULGU-UHFFFAOYSA-N methyl pyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC=C1 OLXYLDUSSBULGU-UHFFFAOYSA-N 0.000 claims description 3
• 230000000394 mitotic effect Effects 0.000 claims description 3
• KBESKGARASQJER-UHFFFAOYSA-N prop-2-enyl 2-bromo-6-(5-chloropyrimidin-2-yl)oxybenzoate Chemical compound BrC1=C(C(=O)OCC=C)C(=CC=C1)OC1=NC=C(C=N1)Cl KBESKGARASQJER-UHFFFAOYSA-N 0.000 claims description 3
• 229950003776 protoporphyrin Drugs 0.000 claims description 3
• QBSOCTPGWBPYNI-UHFFFAOYSA-N 1-[2-(5-bromopyrimidin-2-yl)oxyphenyl]ethanone Chemical compound CC(=O)C1=CC=CC=C1OC1=NC=C(Br)C=N1 QBSOCTPGWBPYNI-UHFFFAOYSA-N 0.000 claims description 2
• OUXHRFRSSZRSMY-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-yl 2-bromo-6-(5-chloropyrimidin-2-yl)oxybenzoate Chemical compound BrC1=C(C(=O)OC(CC(F)(F)F)C)C(=CC=C1)OC1=NC=C(C=N1)Cl OUXHRFRSSZRSMY-UHFFFAOYSA-N 0.000 claims description 2
• 239000005476 Bentazone Substances 0.000 claims description 2
• 239000005561 Glufosinate Substances 0.000 claims description 2
• 108010051696 Growth Hormone Proteins 0.000 claims description 2
• 102100038803 Somatotropin Human genes 0.000 claims description 2
• 108090000992 Transferases Proteins 0.000 claims description 2
• 102000004357 Transferases Human genes 0.000 claims description 2
• 239000005626 Tribenuron Substances 0.000 claims description 2
• LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 claims description 2
• TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 claims description 2
• CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzidamine Natural products C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 claims description 2
• 125000005159 cyanoalkoxy group Chemical group 0.000 claims description 2
• 239000000122 growth hormone Substances 0.000 claims description 2
• BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 claims description 2
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