ES2593275T3 - Compuestos herbicidas - Google Patents
Compuestos herbicidas Download PDFInfo
- Publication number
- ES2593275T3 ES2593275T3 ES13712559.7T ES13712559T ES2593275T3 ES 2593275 T3 ES2593275 T3 ES 2593275T3 ES 13712559 T ES13712559 T ES 13712559T ES 2593275 T3 ES2593275 T3 ES 2593275T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- alkoxy
- group
- haloalkyl
- aryl
- 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.)
- Active
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- 150000001875 compounds Chemical class 0.000 title abstract description 28
- 230000002363 herbicidal effect Effects 0.000 title description 4
- 125000003118 aryl group Chemical group 0.000 abstract description 13
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 6
- -1 C1- alkoxy C3 Chemical group 0.000 abstract description 5
- 239000000460 chlorine Chemical group 0.000 abstract description 4
- 150000003839 salts Chemical class 0.000 abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 27
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 17
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 16
- 125000001188 haloalkyl group Chemical group 0.000 abstract 11
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 10
- 229910052736 halogen Inorganic materials 0.000 abstract 10
- 150000002367 halogens Chemical class 0.000 abstract 10
- 125000001424 substituent group Chemical group 0.000 abstract 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 8
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 abstract 7
- 239000001257 hydrogen Substances 0.000 abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 6
- 229910052760 oxygen Inorganic materials 0.000 abstract 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 5
- 125000003545 alkoxy group Chemical group 0.000 abstract 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 5
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 5
- 239000001301 oxygen Substances 0.000 abstract 5
- 229910052717 sulfur Inorganic materials 0.000 abstract 5
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 abstract 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 4
- 125000005842 heteroatom Chemical group 0.000 abstract 4
- 229910052757 nitrogen Inorganic materials 0.000 abstract 4
- 239000011593 sulfur Substances 0.000 abstract 4
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 abstract 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 abstract 3
- 125000003342 alkenyl group Chemical group 0.000 abstract 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000000304 alkynyl group Chemical group 0.000 abstract 3
- 125000006310 cycloalkyl amino group Chemical group 0.000 abstract 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 3
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 abstract 2
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 abstract 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 2
- 125000003282 alkyl amino group Chemical group 0.000 abstract 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 abstract 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 2
- 125000004104 aryloxy group Chemical group 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 2
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 abstract 2
- 239000011737 fluorine Chemical group 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 abstract 2
- 125000005553 heteroaryloxy group Chemical group 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 abstract 1
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 abstract 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 abstract 1
- 125000006799 (C2-C6) alkenylamino group Chemical group 0.000 abstract 1
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000004658 aryl carbonyl amino group Chemical group 0.000 abstract 1
- 125000005129 aryl carbonyl group Chemical group 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 125000000000 cycloalkoxy group Chemical group 0.000 abstract 1
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 abstract 1
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 1
- 125000005347 halocycloalkyl group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000002950 monocyclic group Chemical group 0.000 abstract 1
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 64
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 20
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 241000196324 Embryophyta Species 0.000 description 9
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 6
- 230000001012 protector Effects 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 4
- 229910052737 gold Inorganic materials 0.000 description 4
- 239000010931 gold Substances 0.000 description 4
- 238000011068 loading method Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000001879 copper Chemical class 0.000 description 3
- OAWUUPVZMNKZRY-UHFFFAOYSA-N cyprosulfamide Chemical compound COC1=CC=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NC2CC2)C=C1 OAWUUPVZMNKZRY-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- 239000002808 molecular sieve Substances 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QNMBSXGYAQZCTN-UHFFFAOYSA-N thiophen-3-ylboronic acid Chemical compound OB(O)C=1C=CSC=1 QNMBSXGYAQZCTN-UHFFFAOYSA-N 0.000 description 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 description 2
- PAQZWJGSJMLPMG-UHFFFAOYSA-N 2,4,6-tripropyl-1,3,5,2$l^{5},4$l^{5},6$l^{5}-trioxatriphosphinane 2,4,6-trioxide Chemical compound CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 244000038559 crop plants Species 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- MIIFHRBUBUHJMC-UHFFFAOYSA-N ethyl 3-oxo-4h-quinoxaline-2-carboxylate Chemical compound C1=CC=C2NC(=O)C(C(=O)OCC)=NC2=C1 MIIFHRBUBUHJMC-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 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 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- XUHGTGGPZFJRMF-UHFFFAOYSA-N 1,3-dihydropyrazole-2-carboxylic acid Chemical compound OC(=O)N1CC=CN1 XUHGTGGPZFJRMF-UHFFFAOYSA-N 0.000 description 1
- RBSXHDIPCIWOMG-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-3-(2-ethylsulfonylimidazo[1,2-a]pyridin-3-yl)sulfonylurea Chemical compound CCS(=O)(=O)C=1N=C2C=CC=CN2C=1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 RBSXHDIPCIWOMG-UHFFFAOYSA-N 0.000 description 1
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 1
- ABOOPXYCKNFDNJ-UHFFFAOYSA-N 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 ABOOPXYCKNFDNJ-UHFFFAOYSA-N 0.000 description 1
- ULRPISSMEBPJLN-UHFFFAOYSA-N 2h-tetrazol-5-amine Chemical compound NC1=NN=NN1 ULRPISSMEBPJLN-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- ZUSHSDOEVHPTCU-UHFFFAOYSA-N 6-chloro-3-phenyl-1h-pyridazin-4-one Chemical compound N1C(Cl)=CC(=O)C(C=2C=CC=CC=2)=N1 ZUSHSDOEVHPTCU-UHFFFAOYSA-N 0.000 description 1
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- PFJJMJDEVDLPNE-UHFFFAOYSA-N Benoxacor Chemical compound C1=CC=C2N(C(=O)C(Cl)Cl)C(C)COC2=C1 PFJJMJDEVDLPNE-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- NRFQZTCQAYEXEE-UHFFFAOYSA-N Fenclorim Chemical compound ClC1=CC(Cl)=NC(C=2C=CC=CC=2)=N1 NRFQZTCQAYEXEE-UHFFFAOYSA-N 0.000 description 1
- 239000005562 Glyphosate Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- IUFUITYPUYMIHI-UHFFFAOYSA-N N-[1-(3,5-dimethylphenoxy)propan-2-yl]-6-(2-fluoropropan-2-yl)-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N)=NC(C(C)(C)F)=NC=1NC(C)COC1=CC(C)=CC(C)=C1 IUFUITYPUYMIHI-UHFFFAOYSA-N 0.000 description 1
- NTBVTCXMRYKRTB-UHFFFAOYSA-N N-{2-[(4,6-dimethoxypyrimidin-2-yl)(hydroxy)methyl]-6-(methoxymethyl)phenyl}-1,1-difluoromethanesulfonamide Chemical compound COCC1=CC=CC(C(O)C=2N=C(OC)C=C(OC)N=2)=C1NS(=O)(=O)C(F)F NTBVTCXMRYKRTB-UHFFFAOYSA-N 0.000 description 1
- 239000005600 Propaquizafop Substances 0.000 description 1
- 239000005601 Propoxycarbazone Substances 0.000 description 1
- 239000005603 Prosulfocarb Substances 0.000 description 1
- 239000005604 Prosulfuron Substances 0.000 description 1
- LTUNNEGNEKBSEH-UHFFFAOYSA-N Prosulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)CCC(F)(F)F)=N1 LTUNNEGNEKBSEH-UHFFFAOYSA-N 0.000 description 1
- 239000005606 Pyridate Substances 0.000 description 1
- JTZCTMAVMHRNTR-UHFFFAOYSA-N Pyridate Chemical compound CCCCCCCCSC(=O)OC1=CC(Cl)=NN=C1C1=CC=CC=C1 JTZCTMAVMHRNTR-UHFFFAOYSA-N 0.000 description 1
- 239000005608 Quinmerac Substances 0.000 description 1
- OBLNWSCLAYSJJR-UHFFFAOYSA-N Quinoclamin Chemical compound C1=CC=C2C(=O)C(N)=C(Cl)C(=O)C2=C1 OBLNWSCLAYSJJR-UHFFFAOYSA-N 0.000 description 1
- 239000002167 Quinoclamine Substances 0.000 description 1
- 239000005609 Quizalofop-P Substances 0.000 description 1
- 239000005616 Rimsulfuron Substances 0.000 description 1
- JXVIIQLNUPXOII-UHFFFAOYSA-N Siduron Chemical compound CC1CCCCC1NC(=O)NC1=CC=CC=C1 JXVIIQLNUPXOII-UHFFFAOYSA-N 0.000 description 1
- 239000005618 Sulcotrione Substances 0.000 description 1
- 239000005619 Sulfosulfuron Substances 0.000 description 1
- 239000005622 Thiencarbazone Substances 0.000 description 1
- QHTQREMOGMZHJV-UHFFFAOYSA-N Thiobencarb Chemical compound CCN(CC)C(=O)SCC1=CC=C(Cl)C=C1 QHTQREMOGMZHJV-UHFFFAOYSA-N 0.000 description 1
- 239000005626 Tribenuron Substances 0.000 description 1
- HFBWPRKWDIRYNX-UHFFFAOYSA-N Trietazine Chemical compound CCNC1=NC(Cl)=NC(N(CC)CC)=N1 HFBWPRKWDIRYNX-UHFFFAOYSA-N 0.000 description 1
- 239000005628 Triflusulfuron Substances 0.000 description 1
- 239000005629 Tritosulfuron Substances 0.000 description 1
- WOAORAPRPVIATR-UHFFFAOYSA-N [3-(trifluoromethyl)phenyl]boronic acid Chemical compound OB(O)C1=CC=CC(C(F)(F)F)=C1 WOAORAPRPVIATR-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- CURLHBZYTFVCRG-UHFFFAOYSA-N butan-2-yl n-(3-chlorophenyl)carbamate Chemical compound CCC(C)OC(=O)NC1=CC=CC(Cl)=C1 CURLHBZYTFVCRG-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- NLKUPINTOLSSLD-UHFFFAOYSA-L calcium;4-(1-oxidopropylidene)-3,5-dioxocyclohexane-1-carboxylate Chemical compound [Ca+2].CCC([O-])=C1C(=O)CC(C([O-])=O)CC1=O NLKUPINTOLSSLD-UHFFFAOYSA-L 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 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 description 1
- JQQWEQHTHRPORN-UHFFFAOYSA-N ethyl 6-fluoro-7-methyl-2-oxo-1h-1,8-naphthyridine-3-carboxylate Chemical compound FC1=C(C)N=C2NC(=O)C(C(=O)OCC)=CC2=C1 JQQWEQHTHRPORN-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- RUCAXVJJQQJZGU-UHFFFAOYSA-M hydron;2-(phosphonatomethylamino)acetate;trimethylsulfanium Chemical compound C[S+](C)C.OP(O)(=O)CNCC([O-])=O RUCAXVJJQQJZGU-UHFFFAOYSA-M 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 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 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- JTHMVYBOQLDDIY-UHFFFAOYSA-N methyl 2-[(4-methyl-5-oxo-3-propoxy-1,2,4-triazole-1-carbonyl)sulfamoyl]benzoate Chemical compound O=C1N(C)C(OCCC)=NN1C(=O)NS(=O)(=O)C1=CC=CC=C1C(=O)OC JTHMVYBOQLDDIY-UHFFFAOYSA-N 0.000 description 1
- PEECTLLHENGOKU-UHFFFAOYSA-N n,n-dimethylpyridin-4-amine Chemical compound CN(C)C1=CC=NC=C1.CN(C)C1=CC=NC=C1 PEECTLLHENGOKU-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- ISEUFVQQFVOBCY-UHFFFAOYSA-N prometon Chemical compound COC1=NC(NC(C)C)=NC(NC(C)C)=N1 ISEUFVQQFVOBCY-UHFFFAOYSA-N 0.000 description 1
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
- FROBCXTULYFHEJ-OAHLLOKOSA-N propaquizafop Chemical compound C1=CC(O[C@H](C)C(=O)OCCON=C(C)C)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 FROBCXTULYFHEJ-OAHLLOKOSA-N 0.000 description 1
- WJNRPILHGGKWCK-UHFFFAOYSA-N propazine Chemical compound CC(C)NC1=NC(Cl)=NC(NC(C)C)=N1 WJNRPILHGGKWCK-UHFFFAOYSA-N 0.000 description 1
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 1
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- YXIIPOGUBVYZIW-UHFFFAOYSA-N pyraflufen Chemical compound ClC1=C(OC(F)F)N(C)N=C1C1=CC(OCC(O)=O)=C(Cl)C=C1F YXIIPOGUBVYZIW-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- DEIKMOQTJBGGAX-DJKKODMXSA-N pyriminobac Chemical compound CO\N=C(/C)C1=CC=CC(OC=2N=C(OC)C=C(OC)N=2)=C1C(O)=O DEIKMOQTJBGGAX-DJKKODMXSA-N 0.000 description 1
- USSIUIGPBLPCDF-KEBDBYFISA-N pyriminobac-methyl Chemical group CO\N=C(/C)C1=CC=CC(OC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC USSIUIGPBLPCDF-KEBDBYFISA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 1
- ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 description 1
- ABOOPXYCKNFDNJ-SNVBAGLBSA-N quizalofop-P Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 ABOOPXYCKNFDNJ-SNVBAGLBSA-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
- 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 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- JRQGDDUXDKCWRF-UHFFFAOYSA-M sodium;n-(2-methoxycarbonylphenyl)sulfonyl-4-methyl-5-oxo-3-propoxy-1,2,4-triazole-1-carboximidate Chemical compound [Na+].O=C1N(C)C(OCCC)=NN1C(=O)[N-]S(=O)(=O)C1=CC=CC=C1C(=O)OC JRQGDDUXDKCWRF-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 description 1
- OORLZFUTLGXMEF-UHFFFAOYSA-N sulfentrazone Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl OORLZFUTLGXMEF-UHFFFAOYSA-N 0.000 description 1
- FZMKKCQHDROFNI-UHFFFAOYSA-N sulfometuron Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 FZMKKCQHDROFNI-UHFFFAOYSA-N 0.000 description 1
- ZDXMLEQEMNLCQG-UHFFFAOYSA-N sulfometuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 ZDXMLEQEMNLCQG-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- GLDAZAQRGCSFNP-UHFFFAOYSA-N thiencarbazone Chemical compound O=C1N(C)C(OC)=NN1C(=O)NS(=O)(=O)C1=C(C)SC=C1C(O)=O GLDAZAQRGCSFNP-UHFFFAOYSA-N 0.000 description 1
- 238000003971 tillage Methods 0.000 description 1
- IYMLUHWAJFXAQP-UHFFFAOYSA-N topramezone Chemical compound CC1=C(C(=O)C2=C(N(C)N=C2)O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 IYMLUHWAJFXAQP-UHFFFAOYSA-N 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-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
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
- RVKCCVTVZORVGD-UHFFFAOYSA-N trinexapac-ethyl Chemical group O=C1CC(C(=O)OCC)CC(=O)C1=C(O)C1CC1 RVKCCVTVZORVGD-UHFFFAOYSA-N 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB201205654 | 2012-03-29 | ||
| GBGB1205654.5A GB201205654D0 (en) | 2012-03-29 | 2012-03-29 | Herbicidal compounds |
| PCT/EP2013/056569 WO2013144231A1 (en) | 2012-03-29 | 2013-03-27 | Herbicidal compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2593275T3 true ES2593275T3 (es) | 2016-12-07 |
Family
ID=46159999
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES13712559.7T Active ES2593275T3 (es) | 2012-03-29 | 2013-03-27 | Compuestos herbicidas |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US9179678B2 (forum.php) |
| EP (1) | EP2831062B1 (forum.php) |
| CN (1) | CN104220436B (forum.php) |
| AR (1) | AR090546A1 (forum.php) |
| AU (1) | AU2013241824B2 (forum.php) |
| BR (1) | BR112014023417B1 (forum.php) |
| CA (1) | CA2865262C (forum.php) |
| ES (1) | ES2593275T3 (forum.php) |
| GB (1) | GB201205654D0 (forum.php) |
| IN (1) | IN2014DN07372A (forum.php) |
| UY (1) | UY34707A (forum.php) |
| WO (1) | WO2013144231A1 (forum.php) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2651491T3 (es) | 2013-05-31 | 2018-01-26 | Nissan Chemical Industries, Ltd. | Compuesto de amida heterocíclico |
| CN104557749B (zh) * | 2014-12-19 | 2017-01-18 | 武汉工程大学 | 3‑苯基‑5‑(4‑三氟甲基苯胺基)‑4h‑1,2,4‑三氮唑及其合成工艺和应用 |
| CN107257799B (zh) * | 2015-02-27 | 2020-07-10 | 先正达参股股份有限公司 | 具有作为除草剂活性的三唑并三嗪酮衍生物 |
| GB201510254D0 (en) | 2015-06-12 | 2015-07-29 | Syngenta Participations Ag | Improvements in or relating to organic compounds |
| KR20180043838A (ko) | 2015-09-11 | 2018-04-30 | 바이엘 크롭사이언스 악티엔게젤샤프트 | Ｈｐｐｄ 변이체 및 사용 방법 |
| BR112019018175A2 (pt) | 2017-03-07 | 2020-04-07 | BASF Agricultural Solutions Seed US LLC | molécula, célula, planta, sementes, polipeptídeos recombinantes, método para produzir um polipeptídeo, planta, método para controlar ervas, uso do ácido nucleico e produto de utilidade |
| AR126963A1 (es) | 2021-09-13 | 2023-12-06 | Lilly Co Eli | Agonistas de ahr |
| TWI838849B (zh) * | 2021-09-13 | 2024-04-11 | 美商美國禮來大藥廠 | Ahr促效劑 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR8600161A (pt) | 1985-01-18 | 1986-09-23 | Plant Genetic Systems Nv | Gene quimerico,vetores de plasmidio hibrido,intermediario,processo para controlar insetos em agricultura ou horticultura,composicao inseticida,processo para transformar celulas de plantas para expressar uma toxina de polipeptideo produzida por bacillus thuringiensis,planta,semente de planta,cultura de celulas e plasmidio |
| ATE84302T1 (de) | 1988-10-20 | 1993-01-15 | Ciba Geigy Ag | Sulfamoylphenylharnstoffe. |
| CA2005658A1 (en) | 1988-12-19 | 1990-06-19 | Eliahu Zlotkin | Insecticidal toxins, genes encoding these toxins, antibodies binding to them and transgenic plant cells and plants expressing these toxins |
| DK0427529T3 (da) | 1989-11-07 | 1995-06-26 | Pioneer Hi Bred Int | Larvedræbende lactiner og planteinsektresistens baseret derpå |
| UA48104C2 (uk) | 1991-10-04 | 2002-08-15 | Новартіс Аг | Фрагмент днк, який містить послідовність,що кодує інсектицидний протеїн, оптимізовану для кукурудзи,фрагмент днк, який забезпечує направлену бажану для серцевини стебла експресію зв'язаного з нею структурного гена в рослині, фрагмент днк, який забезпечує специфічну для пилку експресію зв`язаного з нею структурного гена в рослині, рекомбінантна молекула днк, спосіб одержання оптимізованої для кукурудзи кодуючої послідовності інсектицидного протеїну, спосіб захисту рослин кукурудзи щонайменше від однієї комахи-шкідника |
| US5530195A (en) | 1994-06-10 | 1996-06-25 | Ciba-Geigy Corporation | Bacillus thuringiensis gene encoding a toxin active against insects |
| AR031027A1 (es) | 2000-10-23 | 2003-09-03 | Syngenta Participations Ag | Composiciones agroquimicas |
| ES2400699T3 (es) | 2000-12-07 | 2013-04-11 | Syngenta Limited | HIDROXI-FENIL PIRUVATO DIOXIGENASAS (HPPD) derivadas de plantas y resistentes frenta a herbicidas tricetónicos, y plantas transgénicas que contienen DIOXIGENASAS |
| AR037856A1 (es) | 2001-12-17 | 2004-12-09 | Syngenta Participations Ag | Evento de maiz |
| PL1789401T3 (pl) | 2004-09-03 | 2010-07-30 | Syngenta Ltd | Pochodne izoksazoliny i ich zastosowanie jako herbicydów |
| GB0603891D0 (en) | 2006-02-27 | 2006-04-05 | Syngenta Ltd | Novel herbicides |
| CN101778832B (zh) | 2007-08-01 | 2014-04-09 | 组合化学工业株式会社 | 氧代吡嗪衍生物及除草剂 |
| US8334236B2 (en) | 2009-02-03 | 2012-12-18 | Kumiai Chemical Industry Co., Ltd. | Ring-fused 2-pyridone derivatives and herbicides |
| EP2417132B1 (en) | 2009-04-06 | 2013-04-17 | Syngenta Limited | Herbicidal quinoline and 1,8-naphthyridine compounds |
| KR101796483B1 (ko) * | 2010-09-01 | 2017-11-10 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | Ｎ-(테트라졸-5-일)- 및 ｎ-(트리아졸-5-일)아릴카복사미드 및 제초제로서의 그의 용도 |
| GB201016761D0 (en) | 2010-10-05 | 2010-11-17 | Syngenta Ltd | Herbicidal compounds |
-
2012
- 2012-03-29 GB GBGB1205654.5A patent/GB201205654D0/en not_active Ceased
-
2013
- 2013-03-27 US US14/389,109 patent/US9179678B2/en active Active
- 2013-03-27 AR ARP130101031A patent/AR090546A1/es active IP Right Grant
- 2013-03-27 BR BR112014023417-5A patent/BR112014023417B1/pt active IP Right Grant
- 2013-03-27 IN IN7372DEN2014 patent/IN2014DN07372A/en unknown
- 2013-03-27 ES ES13712559.7T patent/ES2593275T3/es active Active
- 2013-03-27 CA CA2865262A patent/CA2865262C/en active Active
- 2013-03-27 AU AU2013241824A patent/AU2013241824B2/en active Active
- 2013-03-27 EP EP13712559.7A patent/EP2831062B1/en active Active
- 2013-03-27 CN CN201380017850.6A patent/CN104220436B/zh active Active
- 2013-03-27 WO PCT/EP2013/056569 patent/WO2013144231A1/en active Application Filing
- 2013-04-01 UY UY0001034707A patent/UY34707A/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| UY34707A (es) | 2013-10-31 |
| AU2013241824A1 (en) | 2014-09-25 |
| CA2865262A1 (en) | 2013-10-03 |
| BR112014023417B1 (pt) | 2019-10-01 |
| US9179678B2 (en) | 2015-11-10 |
| EP2831062A1 (en) | 2015-02-04 |
| IN2014DN07372A (forum.php) | 2015-04-24 |
| CA2865262C (en) | 2020-06-09 |
| AU2013241824B2 (en) | 2017-04-20 |
| CN104220436B (zh) | 2017-04-26 |
| WO2013144231A1 (en) | 2013-10-03 |
| GB201205654D0 (en) | 2012-05-16 |
| EP2831062B1 (en) | 2016-07-27 |
| US20150087513A1 (en) | 2015-03-26 |
| AR090546A1 (es) | 2014-11-19 |
| CN104220436A (zh) | 2014-12-17 |
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