JP2017522317A5 - - Google Patents
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- JP2017522317A5 JP2017522317A5 JP2017502261A JP2017502261A JP2017522317A5 JP 2017522317 A5 JP2017522317 A5 JP 2017522317A5 JP 2017502261 A JP2017502261 A JP 2017502261A JP 2017502261 A JP2017502261 A JP 2017502261A JP 2017522317 A5 JP2017522317 A5 JP 2017522317A5
- Authority
- JP
- Japan
- Prior art keywords
- haloalkyl
- yloxy
- phenoxy
- pyrimidine
- chloropyridin
- Prior art date
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 12
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 12
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 11
- 230000002363 herbicidal effect Effects 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 239000004009 herbicide Substances 0.000 claims description 6
- 238000009472 formulation Methods 0.000 claims description 5
- 239000004615 ingredient Substances 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 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 4
- 239000007787 solid Substances 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- 150000001204 N-oxides Chemical class 0.000 claims description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 2
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 description 5
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 2
- 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 description 2
- 108010000700 Acetolactate synthase Proteins 0.000 description 2
- 239000005504 Dicamba Substances 0.000 description 2
- 239000005562 Glyphosate Substances 0.000 description 2
- 239000005578 Mesotrione Substances 0.000 description 2
- 108020001991 Protoporphyrinogen Oxidase Proteins 0.000 description 2
- 102000005135 Protoporphyrinogen oxidase Human genes 0.000 description 2
- -1 chloranthram-methyl Chemical compound 0.000 description 2
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 2
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 2
- 229940097068 glyphosate Drugs 0.000 description 2
- 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 description 2
- 150000004669 very long chain fatty acids Chemical class 0.000 description 2
- AIAYSXFWIUNXRC-PHIMTYICSA-N (1r,5s)-3-[hydroxy-[2-(2-methoxyethoxymethyl)-6-(trifluoromethyl)pyridin-3-yl]methylidene]bicyclo[3.2.1]octane-2,4-dione Chemical compound COCCOCC1=NC(C(F)(F)F)=CC=C1C(O)=C1C(=O)[C@@H](C2)CC[C@@H]2C1=O AIAYSXFWIUNXRC-PHIMTYICSA-N 0.000 description 1
- FZINUKAJPUUBKY-UHFFFAOYSA-N 2,3-bis[(5-bromopyrimidin-2-yl)oxy]benzonitrile Chemical compound BrC=1C=NC(=NC=1)OC1=C(C#N)C=CC=C1OC1=NC=C(C=N1)Br FZINUKAJPUUBKY-UHFFFAOYSA-N 0.000 description 1
- PSPHNVVPCWJCQH-UHFFFAOYSA-N 2,3-bis[(5-chloropyrimidin-2-yl)oxy]benzonitrile Chemical compound ClC=1C=NC(=NC=1)OC1=C(C#N)C=CC=C1OC1=NC=C(C=N1)Cl PSPHNVVPCWJCQH-UHFFFAOYSA-N 0.000 description 1
- MVWLJDBSOSLWDO-UHFFFAOYSA-N 2,3-bis[(5-fluoropyrimidin-2-yl)oxy]benzonitrile Chemical compound FC=1C=NC(=NC=1)OC1=C(C#N)C=CC=C1OC1=NC=C(C=N1)F MVWLJDBSOSLWDO-UHFFFAOYSA-N 0.000 description 1
- WBRWNKRQDNJQNV-UHFFFAOYSA-N 2-(5-bromopyrimidin-2-yl)oxy-3-(5-chloropyrimidin-2-yl)oxybenzonitrile Chemical compound BrC=1C=NC(=NC=1)OC1=C(C#N)C=CC=C1OC1=NC=C(C=N1)Cl WBRWNKRQDNJQNV-UHFFFAOYSA-N 0.000 description 1
- WGEOOKMZWCRDTD-UHFFFAOYSA-N 2-(5-chloropyrazin-2-yl)oxy-3-(5-chloropyrimidin-2-yl)oxybenzonitrile Chemical compound ClC=1N=CC(=NC=1)OC1=C(C#N)C=CC=C1OC1=NC=C(C=N1)Cl WGEOOKMZWCRDTD-UHFFFAOYSA-N 0.000 description 1
- PYPYUIDDNZJMQP-UHFFFAOYSA-N 2-(5-chloropyridin-2-yl)oxy-3-(5-chloropyrimidin-2-yl)oxybenzonitrile Chemical compound ClC=1C=CC(=NC=1)OC1=C(C#N)C=CC=C1OC1=NC=C(C=N1)Cl PYPYUIDDNZJMQP-UHFFFAOYSA-N 0.000 description 1
- VSFSAIDXPXDEPK-UHFFFAOYSA-N 2-(5-chloropyrimidin-2-yl)oxy-3-[5-(trifluoromethyl)pyrimidin-2-yl]oxybenzonitrile Chemical compound ClC=1C=NC(=NC=1)OC1=C(C#N)C=CC=C1OC1=NC=C(C=N1)C(F)(F)F VSFSAIDXPXDEPK-UHFFFAOYSA-N 0.000 description 1
- ZNDQKNWMZMODAR-UHFFFAOYSA-N 2-[2-(5-bromopyrimidin-2-yl)oxy-3-chlorophenoxy]-5-chloropyrimidine Chemical compound BrC=1C=NC(=NC=1)OC1=C(C=CC=C1OC1=NC=C(C=N1)Cl)Cl ZNDQKNWMZMODAR-UHFFFAOYSA-N 0.000 description 1
- IJAQTDIRUAHWED-UHFFFAOYSA-N 2-[2-(5-bromopyrimidin-2-yl)oxy-3-fluorophenoxy]-5-chloropyrimidine Chemical compound BrC=1C=NC(=NC=1)OC1=C(C=CC=C1OC1=NC=C(C=N1)Cl)F IJAQTDIRUAHWED-UHFFFAOYSA-N 0.000 description 1
- LLGRXXOXRLWZGJ-UHFFFAOYSA-N 2-[2-(5-chloropyrimidin-2-yl)oxy-3-fluorophenoxy]-5-(trifluoromethyl)pyrimidine Chemical compound ClC=1C=NC(=NC=1)OC1=C(C=CC=C1OC1=NC=C(C=N1)C(F)(F)F)F LLGRXXOXRLWZGJ-UHFFFAOYSA-N 0.000 description 1
- BFIWCFMNYOVVGO-UHFFFAOYSA-N 2-[2-(5-chloropyrimidin-2-yl)oxy-6-fluorophenoxy]-5-(trifluoromethyl)pyrimidine Chemical compound ClC=1C=NC(=NC=1)OC1=CC=CC(=C1OC1=NC=C(C=N1)C(F)(F)F)F BFIWCFMNYOVVGO-UHFFFAOYSA-N 0.000 description 1
- KYTIYQSRDHYZGY-UHFFFAOYSA-N 2-[2-bromo-6-(5-chloropyrimidin-2-yl)oxyphenoxy]-5-(difluoromethyl)-1,3-thiazole Chemical compound BrC=1C(=C(OC2=NC=C(C=N2)Cl)C=CC=1)OC=1SC(=CN=1)C(F)F KYTIYQSRDHYZGY-UHFFFAOYSA-N 0.000 description 1
- ZLVABPAEESAVSF-UHFFFAOYSA-N 2-[2-bromo-6-(5-chloropyrimidin-2-yl)oxyphenoxy]-5-chloropyrimidine Chemical compound BrC=1C(=C(C=CC=1)OC1=NC=C(C=N1)Cl)OC1=NC=C(C=N1)Cl ZLVABPAEESAVSF-UHFFFAOYSA-N 0.000 description 1
- SGSAOQOWQNQQAS-UHFFFAOYSA-N 2-[2-chloro-6-(5-chloropyrimidin-2-yl)oxyphenoxy]-5-fluoropyrimidine Chemical compound ClC=1C=NC(=NC=1)OC1=CC=CC(=C1OC1=NC=C(C=N1)F)Cl SGSAOQOWQNQQAS-UHFFFAOYSA-N 0.000 description 1
- GITZJNKISOHCAF-UHFFFAOYSA-N 2-[3,6-difluoro-2-(5-fluoropyrimidin-2-yl)oxyphenoxy]-5-fluoropyrimidine Chemical compound FC=1C(=C(C(=CC=1)F)OC1=NC=C(C=N1)F)OC1=NC=C(C=N1)F GITZJNKISOHCAF-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 1
- KQTAQGSZDVFUBR-UHFFFAOYSA-N 3-(5-bromopyrimidin-2-yl)oxy-2-(5-chloropyrimidin-2-yl)oxybenzonitrile Chemical compound BrC=1C=NC(=NC=1)OC=1C(=C(C#N)C=CC=1)OC1=NC=C(C=N1)Cl KQTAQGSZDVFUBR-UHFFFAOYSA-N 0.000 description 1
- HRIIQHNWGPEYGN-UHFFFAOYSA-N 3-(5-chloropyrimidin-2-yl)oxy-2-[5-(trifluoromethyl)pyrimidin-2-yl]oxybenzonitrile Chemical compound ClC=1C=NC(=NC=1)OC=1C(=C(C#N)C=CC=1)OC1=NC=C(C=N1)C(F)(F)F HRIIQHNWGPEYGN-UHFFFAOYSA-N 0.000 description 1
- UVBVPIVGEVJYLZ-UHFFFAOYSA-N 5-chloro-2-[2-(5-chloropyrimidin-2-yl)oxy-3,6-difluorophenoxy]pyrimidine Chemical compound FC=1C(=C(C(=CC=1)F)OC1=NC=C(C=N1)Cl)OC1=NC=C(C=N1)Cl UVBVPIVGEVJYLZ-UHFFFAOYSA-N 0.000 description 1
- VQFMGWLBXRCPTD-UHFFFAOYSA-N 5-chloro-2-[2-(5-chloropyrimidin-2-yl)oxy-3-(difluoromethyl)phenoxy]pyrimidine Chemical compound FC(C=1C(=C(C=CC=1)OC1=NC=C(C=N1)Cl)OC1=NC=C(C=N1)Cl)F VQFMGWLBXRCPTD-UHFFFAOYSA-N 0.000 description 1
- OMMIWKYCZUWCGH-UHFFFAOYSA-N 5-chloro-2-[2-(5-chloropyrimidin-2-yl)oxy-3-fluorophenoxy]pyrimidine Chemical compound FC=1C(=C(C=CC=1)OC1=NC=C(C=N1)Cl)OC1=NC=C(C=N1)Cl OMMIWKYCZUWCGH-UHFFFAOYSA-N 0.000 description 1
- VTNQPKFIQCLBDU-UHFFFAOYSA-N Acetochlor Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1CC VTNQPKFIQCLBDU-UHFFFAOYSA-N 0.000 description 1
- 229930192334 Auxin Natural products 0.000 description 1
- 239000005476 Bentazone Substances 0.000 description 1
- 239000005492 Carfentrazone-ethyl Substances 0.000 description 1
- 102000016680 Dioxygenases Human genes 0.000 description 1
- 108010028143 Dioxygenases Proteins 0.000 description 1
- 229940106987 Elongase inhibitor Drugs 0.000 description 1
- 239000005561 Glufosinate Substances 0.000 description 1
- 239000005574 MCPA Substances 0.000 description 1
- 239000005584 Metsulfuron-methyl Substances 0.000 description 1
- 239000005586 Nicosulfuron Substances 0.000 description 1
- 108010060806 Photosystem II Protein Complex Proteins 0.000 description 1
- 239000005616 Rimsulfuron Substances 0.000 description 1
- 239000005620 Tembotrione Substances 0.000 description 1
- 239000005623 Thifensulfuron-methyl Substances 0.000 description 1
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 1
- 239000005626 Tribenuron Substances 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 1
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 1
- 239000002363 auxin Substances 0.000 description 1
- ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 description 1
- CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzidamine Natural products C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 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 description 1
- 230000000694 effects Effects 0.000 description 1
- 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 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 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 description 1
- YUCFVHQCAFKDQG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH] YUCFVHQCAFKDQG-UHFFFAOYSA-N 0.000 description 1
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 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 description 1
- OLZQTUCTGLHFTQ-UHFFFAOYSA-N octan-2-yl 2-(4-amino-3,5-dichloro-6-fluoropyridin-2-yl)oxyacetate Chemical group CCCCCCC(C)OC(=O)COC1=NC(F)=C(Cl)C(N)=C1Cl OLZQTUCTGLHFTQ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462024414P | 2014-07-14 | 2014-07-14 | |
| US62/024,414 | 2014-07-14 | ||
| US201562166759P | 2015-05-27 | 2015-05-27 | |
| US62/166,759 | 2015-05-27 | ||
| PCT/US2015/038778 WO2016010731A1 (en) | 2014-07-14 | 2015-07-01 | Bis(aryl)catechol derivatives as herbicides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2017522317A JP2017522317A (ja) | 2017-08-10 |
| JP2017522317A5 true JP2017522317A5 (https=) | 2018-08-09 |
Family
ID=53682826
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017502261A Pending JP2017522317A (ja) | 2014-07-14 | 2015-07-01 | 除草剤としてのビス（アリール）カテコール誘導体 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US20170190671A1 (https=) |
| EP (1) | EP3169676A1 (https=) |
| JP (1) | JP2017522317A (https=) |
| KR (1) | KR20170032355A (https=) |
| CN (1) | CN106488913A (https=) |
| AU (1) | AU2015290153A1 (https=) |
| BR (1) | BR112017000745A2 (https=) |
| CA (1) | CA2954627A1 (https=) |
| CL (1) | CL2017000103A1 (https=) |
| CO (1) | CO2017000337A2 (https=) |
| IL (1) | IL249841A0 (https=) |
| MX (1) | MX2017000594A (https=) |
| PE (1) | PE20170439A1 (https=) |
| RU (1) | RU2017104513A (https=) |
| SG (1) | SG11201700033YA (https=) |
| TW (1) | TW201625554A (https=) |
| UY (1) | UY36210A (https=) |
| WO (1) | WO2016010731A1 (https=) |
| ZA (1) | ZA201700119B (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA124329C2 (uk) | 2014-01-16 | 2021-09-01 | ЕфЕмСі КОРПОРЕЙШН | Піримідинілоксибензольні похідні як гербіциди |
| MX395250B (es) | 2015-03-18 | 2025-03-25 | Fmc Corp Star | Derivados de pirimidiniloxipiridina sustituidos como herbicidas. |
| TWI828952B (zh) | 2015-06-05 | 2024-01-11 | 美商艾佛艾姆希公司 | 作為除草劑之嘧啶氧基苯衍生物 |
| CA2990839A1 (en) | 2015-07-13 | 2017-01-19 | E.I. Du Pont De Nemours & Company | Aryloxypyrimidinyl ethers as herbicides |
| CA3062135A1 (en) | 2017-05-02 | 2018-11-08 | Fmc Corporation | Pyrimidinyloxy benzo-fused compounds as herbicides |
| EA202190111A1 (ru) | 2018-06-25 | 2021-04-23 | Байер Акциенгезельшафт | Замещенные гетероарилоксипиридины и их соли, а также их применение в качестве гербицидных действующих веществ |
| CN119039233A (zh) * | 2018-09-27 | 2024-11-29 | Fmc公司 | 哒嗪酮除草剂和用于制备除草剂的哒嗪酮中间体 |
| EP3670505A1 (de) * | 2018-12-18 | 2020-06-24 | Bayer AG | Substituierte pyridinyloxybenzole sowie deren salze und ihre verwendung als herbizide wirkstoffe |
| BR112021019111A2 (pt) | 2019-03-27 | 2021-11-30 | Bayer Ag | 2-heteroarilaminobenzenos substituídos assim como seus sais e sua aplicação como substância ativa herbicida |
| GB202005175D0 (en) * | 2020-04-08 | 2020-05-20 | Syngenta Crop Protection Ag | Improvements in or relating to organic compounds |
| JP2024506004A (ja) | 2021-02-04 | 2024-02-08 | バイエル、アクチエンゲゼルシャフト | 置換された（２－ヘテロアリールオキシフェニル）スルホネート、その塩およびそれらの除草剤としての使用 |
| EP4499613A1 (de) | 2022-03-28 | 2025-02-05 | Bayer Aktiengesellschaft | Substituierte 2-c-azine sowie deren salze und ihre verwendung als herbizide wirkstoffe |
| JP2025512828A (ja) * | 2022-03-28 | 2025-04-22 | バイエル・アクチエンゲゼルシヤフト | 置換２－アミノアジンおよびその塩、ならびにその除草性活性物質としての使用 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2891855A (en) | 1954-08-16 | 1959-06-23 | Geigy Ag J R | Compositions and methods for influencing the growth of plants |
| US3235361A (en) | 1962-10-29 | 1966-02-15 | Du Pont | Method for the control of undesirable vegetation |
| US3060084A (en) | 1961-06-09 | 1962-10-23 | Du Pont | Improved homogeneous, readily dispersed, pesticidal concentrate |
| US3299566A (en) | 1964-06-01 | 1967-01-24 | Olin Mathieson | Water soluble film containing agricultural chemicals |
| US3309192A (en) | 1964-12-02 | 1967-03-14 | Du Pont | Method of controlling seedling weed grasses |
| US4144050A (en) | 1969-02-05 | 1979-03-13 | Hoechst Aktiengesellschaft | Micro granules for pesticides and process for their manufacture |
| US3920442A (en) | 1972-09-18 | 1975-11-18 | Du Pont | Water-dispersible pesticide aggregates |
| US4172714A (en) | 1976-12-20 | 1979-10-30 | E. I. Du Pont De Nemours And Company | Dry compactible, swellable herbicidal compositions and pellets produced therefrom |
| NZ188244A (en) * | 1977-09-13 | 1981-04-24 | Ici Australia Ltd | 2-substituted pyrimidines compositions growth regulating processes |
| CH639056A5 (de) * | 1977-11-04 | 1983-10-31 | Ciba Geigy Ag | Verfahren zur herstellung von hydroxydiarylaethern. |
| NZ191078A (en) * | 1978-08-08 | 1982-05-31 | Ici Australia Ltd | Bis(pyrimidyloxy) benzenes bis(pyrimidylthio)benzenes and prymidyloxy-pyrimidyl thiobenzens and herbicidal compositions |
| JPS5524195A (en) * | 1978-08-08 | 1980-02-21 | Ici Australia Ltd | Herbicide compound and composition*their manufacture and their use |
| US4371736A (en) * | 1981-03-27 | 1983-02-01 | E. I. Du Pont De Nemours And Company | Herbicidal pyridinyloxy(pyrimidinyloxy)benzenes |
| GB2095558B (en) | 1981-03-30 | 1984-10-24 | Avon Packers Ltd | Formulation of agricultural chemicals |
| DE3246493A1 (de) | 1982-12-16 | 1984-06-20 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von wasserdispergierbaren granulaten |
| DE58907484D1 (de) * | 1988-06-16 | 1994-05-26 | Basf Ag | Salicylsäurederivate und deren Schwefelanaloge. |
| US5180587A (en) | 1988-06-28 | 1993-01-19 | E. I. Du Pont De Nemours And Company | Tablet formulations of pesticides |
| DE69033861T2 (de) | 1989-08-30 | 2002-06-06 | Kynoch Agrochemicals (Proprietary) Ltd., Sandton | Herstellung eines Dosierungsmittels |
| ES2065680T3 (es) | 1990-03-12 | 1995-02-16 | Du Pont | Granulos de plaguicida dispersables en agua o solubles en agua a partir de aglutinantes activados por calor. |
| EP0480679B1 (en) | 1990-10-11 | 1996-09-18 | Sumitomo Chemical Company Limited | Pesticidal composition |
| TWI283164B (en) | 2001-09-21 | 2007-07-01 | Du Pont | Anthranilamide arthropodicide treatment |
-
2015
- 2015-06-30 TW TW104121069A patent/TW201625554A/zh unknown
- 2015-07-01 CA CA2954627A patent/CA2954627A1/en not_active Abandoned
- 2015-07-01 KR KR1020177003603A patent/KR20170032355A/ko not_active Withdrawn
- 2015-07-01 BR BR112017000745A patent/BR112017000745A2/pt not_active Application Discontinuation
- 2015-07-01 JP JP2017502261A patent/JP2017522317A/ja active Pending
- 2015-07-01 US US15/325,251 patent/US20170190671A1/en not_active Abandoned
- 2015-07-01 RU RU2017104513A patent/RU2017104513A/ru not_active Application Discontinuation
- 2015-07-01 CN CN201580037650.6A patent/CN106488913A/zh active Pending
- 2015-07-01 MX MX2017000594A patent/MX2017000594A/es unknown
- 2015-07-01 EP EP15739416.4A patent/EP3169676A1/en not_active Withdrawn
- 2015-07-01 PE PE2017000053A patent/PE20170439A1/es unknown
- 2015-07-01 WO PCT/US2015/038778 patent/WO2016010731A1/en not_active Ceased
- 2015-07-01 AU AU2015290153A patent/AU2015290153A1/en not_active Abandoned
- 2015-07-01 SG SG11201700033YA patent/SG11201700033YA/en unknown
- 2015-07-10 UY UY0001036210A patent/UY36210A/es not_active Application Discontinuation
-
2016
- 2016-12-29 IL IL249841A patent/IL249841A0/en unknown
-
2017
- 2017-01-05 ZA ZA2017/00119A patent/ZA201700119B/en unknown
- 2017-01-13 CO CONC2017/0000337A patent/CO2017000337A2/es unknown
- 2017-01-13 CL CL2017000103A patent/CL2017000103A1/es unknown
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