CZ298793B6 - Selektivní herbicidy na bázi N-aryl-triazolin(thi)onu a N-arylsulfonylamino(thio)karbonyl-triazolin(thi)onu, zpusob jejich výroby a jejich použití - Google Patents
Selektivní herbicidy na bázi N-aryl-triazolin(thi)onu a N-arylsulfonylamino(thio)karbonyl-triazolin(thi)onu, zpusob jejich výroby a jejich použití Download PDFInfo
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- CZ298793B6 CZ298793B6 CZ20002715A CZ20002715A CZ298793B6 CZ 298793 B6 CZ298793 B6 CZ 298793B6 CZ 20002715 A CZ20002715 A CZ 20002715A CZ 20002715 A CZ20002715 A CZ 20002715A CZ 298793 B6 CZ298793 B6 CZ 298793B6
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- CZ
- Czechia
- Prior art keywords
- cyano
- substituted
- optionally
- butyl
- sec
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- 238000002360 preparation method Methods 0.000 title description 11
- 239000004009 herbicide Substances 0.000 title description 7
- 238000000034 method Methods 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims abstract description 21
- 239000004480 active ingredient Substances 0.000 claims abstract description 19
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 12
- 239000011885 synergistic combination Substances 0.000 claims abstract description 7
- -1 cyano, thiocarbamoyl Chemical group 0.000 claims description 318
- 150000001875 compounds Chemical class 0.000 claims description 47
- 125000004432 carbon atom Chemical group C* 0.000 claims description 46
- 229910052801 chlorine Inorganic materials 0.000 claims description 41
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 39
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
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- CGFLWJAUGWXXMI-UHFFFAOYSA-N n-[2-cyano-5-[3-(difluoromethyl)-4-ethyl-5-oxo-1,2,4-triazol-1-yl]-4-fluorophenyl]methanesulfonamide Chemical compound O=C1N(CC)C(C(F)F)=NN1C1=CC(NS(C)(=O)=O)=C(C#N)C=C1F CGFLWJAUGWXXMI-UHFFFAOYSA-N 0.000 description 1
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- QVJUQOJYAQWGGO-UHFFFAOYSA-N n-[2-cyano-5-[3-(difluoromethyl)-4-methyl-5-oxo-1,2,4-triazol-1-yl]-4-fluorophenyl]methanesulfonamide Chemical compound O=C1N(C)C(C(F)F)=NN1C1=CC(NS(C)(=O)=O)=C(C#N)C=C1F QVJUQOJYAQWGGO-UHFFFAOYSA-N 0.000 description 1
- YGENZTWYWRSFQF-UHFFFAOYSA-N n-[2-cyano-5-[4-ethyl-5-oxo-3-(trifluoromethyl)-1,2,4-triazol-1-yl]-4-fluorophenyl]ethanesulfonamide Chemical compound O=C1N(CC)C(C(F)(F)F)=NN1C1=CC(NS(=O)(=O)CC)=C(C#N)C=C1F YGENZTWYWRSFQF-UHFFFAOYSA-N 0.000 description 1
- AIRTYRVEGFSXFL-UHFFFAOYSA-N n-[2-cyano-5-[4-ethyl-5-oxo-3-(trifluoromethyl)-1,2,4-triazol-1-yl]-4-fluorophenyl]methanesulfonamide Chemical compound O=C1N(CC)C(C(F)(F)F)=NN1C1=CC(NS(C)(=O)=O)=C(C#N)C=C1F AIRTYRVEGFSXFL-UHFFFAOYSA-N 0.000 description 1
- ZWRDBWDXRLPESY-UHFFFAOYSA-N n-benzyl-n-ethylethanamine Chemical compound CCN(CC)CC1=CC=CC=C1 ZWRDBWDXRLPESY-UHFFFAOYSA-N 0.000 description 1
- HVAAHUDGWQAAOJ-UHFFFAOYSA-N n-benzylethanamine Chemical compound CCNCC1=CC=CC=C1 HVAAHUDGWQAAOJ-UHFFFAOYSA-N 0.000 description 1
- OBYVIBDTOCAXSN-UHFFFAOYSA-N n-butan-2-ylbutan-2-amine Chemical compound CCC(C)NC(C)CC OBYVIBDTOCAXSN-UHFFFAOYSA-N 0.000 description 1
- XRKQMIFKHDXFNQ-UHFFFAOYSA-N n-cyclohexyl-n-ethylcyclohexanamine Chemical compound C1CCCCC1N(CC)C1CCCCC1 XRKQMIFKHDXFNQ-UHFFFAOYSA-N 0.000 description 1
- CRYMTEHEKQNKEB-UHFFFAOYSA-N n-cyclopentyl-n-ethylcyclopentanamine Chemical compound C1CCCC1N(CC)C1CCCC1 CRYMTEHEKQNKEB-UHFFFAOYSA-N 0.000 description 1
- JNMBQGIZTCTCRT-UHFFFAOYSA-N n-cyclopentyl-n-methylcyclopentanamine Chemical compound C1CCCC1N(C)C1CCCC1 JNMBQGIZTCTCRT-UHFFFAOYSA-N 0.000 description 1
- FUUUBHCENZGYJA-UHFFFAOYSA-N n-cyclopentylcyclopentanamine Chemical compound C1CCCC1NC1CCCC1 FUUUBHCENZGYJA-UHFFFAOYSA-N 0.000 description 1
- AGVKXDPPPSLISR-UHFFFAOYSA-N n-ethylcyclohexanamine Chemical compound CCNC1CCCCC1 AGVKXDPPPSLISR-UHFFFAOYSA-N 0.000 description 1
- SRTHFWNTKVOSBA-UHFFFAOYSA-N n-ethylcyclopentanamine Chemical compound CCNC1CCCC1 SRTHFWNTKVOSBA-UHFFFAOYSA-N 0.000 description 1
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- KKTBUCVHSCATGB-UHFFFAOYSA-N n-methylcyclopentanamine Chemical compound CNC1CCCC1 KKTBUCVHSCATGB-UHFFFAOYSA-N 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
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- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 229910052625 palygorskite Inorganic materials 0.000 description 1
- IGEIPFLJVCPEKU-UHFFFAOYSA-N pentan-2-amine Chemical compound CCCC(C)N IGEIPFLJVCPEKU-UHFFFAOYSA-N 0.000 description 1
- 229940100684 pentylamine Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Substances [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- TURAMGVWNUTQKH-UHFFFAOYSA-N propa-1,2-dien-1-one Chemical group C=C=C=O TURAMGVWNUTQKH-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 1
- DROIHSMGGKKIJT-UHFFFAOYSA-N propane-1-sulfonamide Chemical compound CCCS(N)(=O)=O DROIHSMGGKKIJT-UHFFFAOYSA-N 0.000 description 1
- SJMCLWCCNYAWRQ-UHFFFAOYSA-N propane-2-sulfonamide Chemical compound CC(C)S(N)(=O)=O SJMCLWCCNYAWRQ-UHFFFAOYSA-N 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
Landscapes
- 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)
Abstract
Herbicidní prostredky, které obsahují synergické kombinace úcinných látek, které zahrnují známé N-aryl-triazolin(thi)ony obecného vzorce I, kde symboly R.sup.1.n., R.sup.2.n., R.sup.3.n., R.sup.4.n.,R.sup.5.n. a Q mají specifický význam a známé N-arylsulfonylamino-(thio)karbonyl-triazolin(thi)ony obecného vzorce II, kde symboly R.sup.6.n., R.sup.7.n., R.sup.8.n., R.sup.9.n., Q.sup.2.n. a Q.sup.3.n. mají specifický význam. Tyto prostredky se mohou použít se zvlášte dobrým úspechem pro selektivní potírání plevelu v ruzných kulturách užitkových rostlin.
Claims (5)
- PATENTOVÉ NÁROKY25 1. Herbicidní prostředek, vyznačující se tím, že obsahuje synergickou kombinaci účinných látek, zahrnující (a) účinné množství alespoň jednoho N-aryl-triazolin(thi)onu obecného vzorce 1 ve kterémQ1 značí atom kyslíku nebo síry, (I)-16CZ 298793 B6R1 značí popřípadě halogenem substituovanou alkylovou skupinu s 1 až 5 uhlíkovými atomy,R2 značí popřípadě halogenem substituovanou alkylovou skupinu s 1 až 5 uhlíkovými atomy,R3 značí vodíkový atom nebo atom halogenu,R4 značí kyanoskupinu, thiokarbamoylovou skupinu nebo atom halogenu a ío R5 značí nitroskupinu, kyanoskupinu, karboxyskupinu, karbamoylovou skupinu, thiokarbamoylovou skupinu, hydroxyskupinu, merkaptoskupinu, aminoskupinu, hydroxyaminoskupinu, aminosulfonylovou skupinu, atom halogenu, vždy popřípadě kyanoskupinou, hydroxyskupinou, alkoxyskupinou s 1 až 4 uhlíkovými atomy, alkylkarbonylovou skupinou s 1 až 4 uhlíkovými atomy v alkylu a/nebo alkoxykarbonylovou skupinou s 1 až 415 uhlíkovými atomy v alkoxylu substituovanou alkylovou, alkoxylovou, alkylthio-, alkylsulfinylovou, alkylsulfonylovou, alkylkarbonylovou, alkoxykarbonylovou nebo alkylaminovou skupinu se vždy 1 až 6 uhlíkovými atomy, popřípadě kyanoskupinou, karboxyskupinou, atomem halogenu a/nebo alkoxykarbonylovou skupinou s 1 až 4 uhlíkovými atomy v alkoxylu substituovanou alkenylovou, alkinylovou, alkenyloxylovou nebo20 alkinyloxylovou skupinu se vždy 2 až 6 uhlíkovými atomy, popřípadě halogenem substituovanou alkylkarbonylaminovou, alkoxykarbonylaminovou, alkylsulfonylaminovou, Ν,Ν-bis-alkylsulfonylaminovou nebo N-alkylkarbonyl-N-alkylsulfonylaminovou skupinu se vždy 1 až 6 uhlíkovými atomy v alkylových skupinách, nebo popřípadě kyanoskupinou, atomem halogenu, alkylovou skupinou s 1 až 4 uhlíkovými atomy, halogen25 alkylovou skupinou s 1 až 4 uhlíkovými atomy, alkoxyskupinou s 1 až 4 uhlíkovými atomy nebo halogenalkoxyskupinou s 1 až 4 uhlíkovými atomy substituovanou N-fenylkarbonylN-alkylsulfonylaminovou, N-pyridylkarbonyl-N-alkylsulfonylaminovou, N-furylkarbonyl-N-alkylsulfonylaminovou nebo N-thienylkarbonyl-N-alkylsulfonylaminovou skupinu se vždy 1 až 6 uhlíkovými atomy v alkylových skupinách, označované jako účinné látky skupiny 1 a (b) účinné množství alespoň jednoho N-arylsulfonylamino(thio)karbonyl-triazolin(thi)onu obecného vzorce II ve kterém
- 2
- 340 Q a Q značí atom kyslíku nebo síry,R6 značí popřípadě kyanoskupinou, atomem halogenu nebo alkoxyskupinou s 1 až
- 4 uhlíkovými atomy substituovanou alkylovou, alkenylovou, alkinylovou, alkoxylovou, alkenyloxylovou, alkylaminovou nebo dialkylaminovou skupinu se vždy až 6 uhlíkovými atomy,45 nebo popřípadě kyanoskupinou, atomem halogenu nebo alkylovou skupinou s 1 až 4 uhlíkovými atomy substituovanou cykloalkylovou, cykloalkylalkylovou nebo cykloalkylaminovou skupinu se vždy 3 až 6 uhlíkovými atomy v cykloalkylových skupinách a popřípadě s 1 až 4 uhlíkovými atomy v alkylové části,- 17CZ 298793 B6R7 značí vodíkový atom, atom halogenu, popřípadě kyanoskupinou, atomem halogenu nebo alkoxyskupinou substituovanou alkylovou, alkoxylovou, alkylthio-, alkylaminovou, dialkylaminovou, alkenylovou, alkinylovou, alkenyloxylovou, alkinyloxylovou, alkenylthio, alkinylthio-, alkenylaminovou nebo alkinylaminovou skupinu se vždy až 6 uhlíko5 vými atomy, nebo popřípadě kyanoskupinou, atomem halogenu nebo alkylovou skupinou s1 až 4 uhlíkovými atomy substituovanou cykloalkylovou, cykloalkoxylovou, cykloalkylthio-, cykloalkylaminovou nebo cykloalkylalkylovou skupinu se vždy 3 až 6 uhlíkovými atomy v cykloalkylových skupinách a popřípadě s 1 až 4 uhlíkovými atomy v alkylových částech, ioR8 značí nitroskupinu, kyanoskupinu, atom halogenu, fenylovou skupinu, fenoxyskupinu, popřípadě kyanoskupinou, atomem halogenu nebo alkoxyskupinou s 1 až 4 uhlíkovými atomy substituovanou alkylovou, alkylkarbonylovou, alkoxylovou, alkoxykarbonylovou, alkylthio-, alkylsulfinylovou, alkylsulfonylovou, dialkylaminosulfonylovou, alkylamino15 vou, alkenylovou, alkenyloxylovou, alkenylthio-, alkenylaminovou, alkinylovou, alkinyloxylovou a alkinylthio- skupinu se vždy až 6 uhlíkovými atomy, nebo popřípadě kyanoskupinou, atomem halogenu nebo alkylovou skupinou s 1 až 4 uhlíkovými atomy substituovanou cykloalkylovou, cykloalkoxylovou, cykloalkylthio- a cykloalkylaminovou skupinu se vždy 3 až 6 uhlíkovými atomy v cykloalkylových skupinách aR9 značí vodíkový atom, nitroskupinu, kyanoskupinu, atom halogenu, fenylovou skupinu, fenoxyskupinu, popřípadě kyanoskupinou, atomem halogenu nebo alkoxyskupinou substituovanou alkylovou, alkylkarbonylovou, alkoxylovou, alkoxykarbonylovou, alkylthio-, alkylsulfinylovou, alkylsulfonylovou, alkylaminovou, alkenylovou, alkenyloxylovou,25 alkenylthio-, alkenylaminovou, alkinylovou, alkinyloxylovou nebo alkinylthioskupinu se vždy až 6 uhlíkovými atomy, nebo popřípadě kyanoskupinou, atomem halogenu nebo alkylovou skupinou s 1 až 4 uhlíkovými atomy substituovanou cykloalkylovou, cykloalkoxylovou, cykloalkylthio- a cykloalkylaminovou skupinu se vždy 3 až 6 uhlíkovými atomy v cykloalkylových skupinách, a/nebo soli sloučeniny obecného vzorce II, označované jako účinné látky skupiny 2.35 2. Herbicidní prostředek podle nároku 1, v y z n a č u j í c í se tím, že obsahuje synergickou kombinaci účinných látek, zahrnující (a) účinné množství alespoň jednoho N-aryl-triazolin(thi)onu obecného vzorce I, ve kterém40 Q1 značí atom kyslíku nebo síry,R1 značí popřípadě fluorem a/nebo chlorem substituovanou methylovou, ethylovou, n-propylovou, izopropylovou, n-butylovou, izobutylovou, sek.-butylovou nebo terc.-butylovou skupinu,2 v,R značí popřípadě fluorem a/nebo chlorem substituovanou methylovou, ethylovou, n-propylovou, izopropylovou, n-butylovou, izobutylovou, sek.-butylovou nebo terc.-butylovou skupinu,50 R3 značí vodíkový atom nebo atom fluoru, chloru nebo bromu,R4 značí kyanoskupinu, thiokarbamoylovou skupinu nebo atom fluoru, chloru nebo bromu aR5 značí nitroskupinu, kyanoskupinu, karboxyskupinu, karbamoylovou skupinu, thiokarba55 moylovou skupinu, hydroxyskupinu, merkaptoskupinu, aminoskupinu, hydroxyamino-18CZ 298793 B6 skupinu, aminosulfonylovou skupinu, atom fluoru, chloru nebo bromu, popřípadě kyanoskupinou, hydroxyskupinou, methoxyskupinou, ethoxyskupinou, acetylovou skupinou, propionylovou skupinou, methoxykarbonylovou skupinou a/nebo ethoxykarbonylovou skupinou substituovanou methylovou, ethylovou, n-propylovou, izopropylovou, n5 butylovou, izobutylovou, sek.-butylovou, terc.-butylovou, methoxylovou, ethoxylovou, npropoxylovou, izopropoxylovou, n-butoxylovou, izobutoxylovou, sek.-butoxylovou, terc.-butoxylovou, methylthio-, ethylthio-, η-propylthio-, izopropylthio, n-butylthio, izobutylthio, sek.-butylthio, terc.-butylthio, methylsulfinylovou, ethylsulfmylovou, methylsulfonylovou, ethylsulfonylovou, acetylovou, propionylovou, n-butyroylovou, izo10 butyroylovou, methoxykarbonylovou, ethoxykarbonylovou, n-propoxykarbonylovou, izopropoxykarbonylovou, methylaminovou, ethylaminovou, n-propylaminovou, izopropylaminovou, n-butylaminovou, izobutylaminovou, sek.-butylaminovou nebo terc.-butylaminovou skupinu, popřípadě kyanoskupinou, karboxyskupinou, atomem fluoru, chloru nebo bromu, methoxykarbonylovou a/nebo ethoxykarbonylovou skupinou substituovanou15 ethenylovou, propenylovou, butenylovou, ethinylovou, propionylovou, butinylovou, propenyloxylovou, butenyloxylovou, propinyloxylovou nebo butinyloxylovou skupinu, popřípadě fluorem a/nebo chlorem substituovanou acetylaminovou, propionylaminovou, methoxykarbonylaminovou, ethoxykarbonylaminovou, methylsulfonylaminovou, ethylsulfonylaminovou, n-propylsulfonylaminovou, izopropylsulfonylaminovou, n-butylsulfo20 nylaminovou, izobutylsulfonylaminovou, sek.-butylsulfonylaminovou, terc.-butylsulfonylaminovou, Ν,Ν-bis-methylsulfonylaminovou, Ν,Ν-bis-ethylsulfonylaminovou, Nethylsulfonyl-N-methylsulfonylaminovou, N-acetyl-N-methylsulfonylaminovou, Npropionyl-N-methylsulfonylaminovou, N-n-butyroyl-N-methylsulfonylaminovou, Nizobutyroyl-N-methylsulfonylaminovou, N-acetyl-N-ethylsulfonylaminovou, n25 propionyl-N-ethylsulfonylaminovou, N-n-butyroyl-N-ethylsulfonylaminovou nebo Nizobutyroyl-N-ethylsulfonylaminovou skupinu, nebo popřípadě kyanoskupinou, atomem fluoru, chloru nebo bromu, methylovou, ethylovou, n-propylovou, izopropylovou, nbutylovou, izobutylovou, sek.-butylovou, terc.-butylovou, trifluormethylovou, methoxylovou, ethoxylovou, n-propoxylovou, izopropoxylovou, difluormethoxylovou nebo tri30 fluormethoxylovou skupinou substituovanou N-fenylkarbonyl-N-methylsulfonylaminovou, N-fenylkarbonyl-N-ethylsulfonylaminovou, N-thienylkarbonyl-N-methylsulfonylaminovou nebo N-thienylkarbonyl-N-ethylsulfonylaminovou skupinu, označované jako účinné látky skupiny 1 a (b) účinné množství alespoň jednoho N-arylsulfonylamino(thio)karbonyl-triazolin(thi)onu obecného vzorce II ve kterémQ2 a Q3 značí atom kyslíku nebo síry,R6 značí popřípadě kyanoskupinou, atomem fluoru, chloru nebo bromu, methoxyskupinou nebo ethoxyskupinou substituovanou methylovou, ethylovou, n-propylovou, izopropylo45 vou, n-butylovou, izobutylovou, sek.-butylovou, terc.-butylovou, ethenylovou, propenylovou, butenylovou, ethinylovou, propinylovou, butinylovou, methoxylovou, ethoxylovou, n-propoxylovou, izopropoxylovou, n-butoxylovou, izobutoxylovou, sek.-butoxylovou, terc.-butoxylovou, propenyloxylovou, butenyloxylovou, methylaminovou, ethylaminovou, n-propylaminovou, izopropylaminovou, n-butylaminovou, izobutylaminovou, sek50 butylaminovou, terc.-butylaminovou, dimethylaminovou nebo diethylaminovou skupinu, nebo popřípadě kyanoskupinou, atomem fluoru, chloru nebo bromu, methylovou, ethylovou, n-propylovou nebo izopropylovou skupinou substituovanou cyklopropylovou, cyklobutylovou, cyklopentylovou, cyklohexylovou, cyklpropylmethylovou, cyklobutylmethylovou, cyklopentylmethylovou, cyklohexylmethylovou, cyklopropylaminovou, cyklobutyl55 aminovou, cyklopentylaminovou nebo cyklohexylaminovou skupinu,-19CZ 298793 B6R7 značí atom fluoru, chloru nebo bromu, popřípadě kyanoskupinou, atomem fluoru nebo chloru, methoxylovou nebo ethoxylovou skupinou substituovanou methylovou, ethylovou, n-propylovou, izopropylovou, n-butylovou, izobutylovou, sek.-butylovou, terc.-butylo5 vou, methoxylovou, ethoxylovou, n-propoxylovou, izopropoxylovou, n-butoxylovou, izobutoxylovou, sek.-butoxylovou, terč-butoxylovou, methylthio-, ethylthio-, n-propylthio-, izopropylthio-, Ν-butylthio-, izobutyltylthio-, sek.-butylthio-, terc.-butylthio, methylaminovou, ethylaminovou, n-propylaminovou, izopropylaminovou, n-butylaminovou, izobutylaminovou, sek.-butylaminovou, terc.-butylaminovou, dimethyl10 aminovou, diethylaminovou, ethenylovou, propenylovou, butenylovou, ethinylovou, propionylovou, butinylovou, ethenyloxylovou, propenyloxylovou, butenyloxylovou, propinyloxylovou, butinyloxylovou, ethenylthio-, propenylthio-, butenylthio-, propinylthio-, butinylthio-, propenylaminovou, butenylaminovou, propinylaminovou nebo butinylaminovou skupinu, nebo popřípadě kyanoskupinou, atomem fluoru, chloru nebo bromu,15 methylovou, ethylovou, n-propylovou nebo izopropylovou skupinou substituovanou cyklopropylovou, cyklobutylovou, cyklopentylovou, cyklohexylovou, cyklopropyloxylovou, cyklobutyloxylovou, cyklopentyloxylovou, cyklohexyloxylovou, cyklopropylthio-, cyklobutylthio-, cyklopentylthio-, cyklohexylthio, cyklopropylaminovou, cyklobutylaminovou, cyklopentylaminovou, cyklohexylaminovou, cyklopropylmethylovou, cyklobutyl20 methylovou, cyklopentylmethylovou nebo cyklohexylmethylovou skupinu,R8 značí nitroskupinu, kyanoskupinu, atom fluoru, chloru nebo bromu, popřípadě kyanoskupinou, atomem fluoru nebo chloru, methoxyskupinou nebo ethoxyskupinou substituovanou methylovou, ethylovou, n-propylovou, izopropylovou, n-butylovou, izobutylovou, sek25 butylovou, terc.-butylovou, acetylovou, propionylovou, n-butyroylovou, izobutyroylovou, methoxylovou, ethoxylovou, n-propoxylovou, izopropoxylovou, n-butoxylovou, izobutoxylovou, sek.-butoxylovou, terc.-butyloxylovou, methoxykarbonylovou, ethoxykarbonylovou, n-propoxykarbonylovou, izopropoxykarbonylovou, methylthio-, ethylthio-, n-propylthio-, izopropylthio-, η-butylthio-, izobutylthio-, sek.-butylthio-, terc.-butylthio-,30 methylsulfínylovou, ethylsulfmylovou, n-propylsulfínylovou, izopropylsulfínylovou, methylsulfonylovou, ethylsulfonylovou, n-propylsulfonylovou, izopropylsulfonylovou, methylaminovou, ethylaminovou, n-propylaminovou, izopropylaminovou, n-butylaminovou, izobutylaminovou, sek.-butylaminovou, terc.-butylaminovou, ethenylovou, propenylovou, butenylovou, propenyloxylovou, butenyloxylovou, propenylthio-, butenylthio-,35 propenylaminovou, butenylaminovou, ethinylovou, propinylovou, butinylovou, propinyloxylovou, butinyloxylovou, propinylthio- nebo butinylthio- skupinu, nebo popřípadě kyanoskupinou, atomem fluoru, chloru nebo bromu, methylovou, ethylovou, n-propylovou nebo izopropylovou skupinou substituovanou cyklopropylovou, cyklobutylovou, cyklopentylovou, cyklohexylovou, cyklopropyloxylovou, cyklobutyloxylovou, cyklopentyl40 oxylovou, cyklohexyloxylovou, cyklopropylthio-, cyklobutylthio-, cyklopentylthio-, cyklohexylthio-, cyklopropylaminovou, cyklobutylaminovou, cyklopentylaminovou nebo cyklohexylaminovou skupinu aR9 značí vodíkový atom, nitroskupinu, kyanoskupinu, atom fluoru, chloru nebo bromu, popří45 pádě kyanoskupinou, atomem fluoru nebo chloru, methoxyskupinou nebo ethoxyskupinou substituovanou methylovou, ethylovou, n-propylovou, izopropylovou, n-butylovou, izobutylovou, sek.-butylovou, terc.-butylovou, acetylovou, propionylovou, n-butyroylovou, izobutyroylovou, methoxylovou, ethoxylovou, n-propoxylovou, izopropoxylovou, nbutoxylovou, izobutoxylovou, sek.-butoxylovou, terč-butoxylovou, methoxykarbonylo50 vou, ethoxykarbonylovou, n-propoxykarbonylovou, izopropoxykarbonylovou, methylthio-, ethylthio-, η-propylthio-, izopropylthio, η-butylhio-, izobutylthio-, sek.-butylthio, terc.-butylthio, methylsulfínylovou, ethylsulfmylovou, n-propylsulfínylovou, izopropylsulfinylovou, methylsulfonylovou, ethylsulfonylovou, n-propylsulfonylovou, izopropylsulfonylovou, methylaminovou, ethylaminovou, n-propylaminovou, izopropylaminovou,55 n-butylaminovou, izobutylaminovou, sek.-butylaminovou, terc.-butylaminovou, etheny-20CZ 298793 B6 lovou, propenylovou, butenylovou, propenyloxylovou, butenyloxylovou, propenylthio-, butenylthio-, propenylaminovou, butenylaminovou, ethinylovou, propinylovou, butinylovou, propinyloxylovou, butinyloxylovou nebo butinylthioskupinu, nebo popřípadě kyanoskupinou, atomem fluoru, chloru nebo bromu, methylovou, ethylovou, n-propylovou nebo
- 5 izopropylovou skupinou substituovanou cyklopropylovou, cyklobutylovou, cyklopentylovou cyklohexylovou, cyklopropyloxylovou, cyklobutyloxylovou, cyklopentyloxylovou, cyklohexyloxylovou, cyklopropylthio-, cyklobutylthio-, cyklopentylthio-, cyklohexylthio-, cyklopropylaminovou, cyklobutylaminovou, cyklopentylaminovou nebo cyklohexylaminovou skupinu, a/nebo solí sloučeniny obecného vzorce II, označované jako účinné látky skupiny 2.15 3. Herbicidní prostředek podle nároku 1, v y z n a č u j í c í se tím, že obsahuje synergickou kombinaci účinných látek, zahrnující (a) účinné množství alespoň jednoho N-aryl-triazolin(thi)onu obecného vzorce I, ve kterém20 Q1 značí atom kyslíku nebo síry,R1 značí methylovou, ethylovou nebo difluormethylovou skupinu,R2 značí methylovou, ethylovou, difluormethylovou, trifluormethylovou, fluorethylovou, di25 fluorethylovou, trifluorethylovou, tetrafluorethylovou nebo pentafluorethylovou skupinu,R3 značí atom fluoru nebo chloru,R4 značí kyanoskupinu, thiokarbamoylovou skupinu nebo atom chloru nebo bromu aR5 značí nitroskupinu, kyanoskupinu, karboxyskupinu, karbamoylovou skupinu, thiokarbamoylovou skupinu, hydroxyskupinu, merkaptoskupinu, aminoskupinu, atom fluoru, chloru nebo bromu, popřípadě kyanoskupinou, methoxyskupinou, ethoxyskupinou, methoxykarbonylovou skupinou a/nebo ethoxykarbonylovou skupinou substituovanou35 methylovou, ethylovou, n-propylovou, izopropylovou, n-butylovou, methoxylovou, ethoxylovou, n-propoxylovou, izopropoxylovou, methylthio-, ethylthio-, η-propylthio-, izopropylthio, methylsulfínylovou, ethylsulfínylovou, methylsulfonylovou, ethylsulfonylovou, methoxykarbonylovou, ethoxykarbonylovou, n-propoxykarbonylovou, izopropoxykarbonylovou, methylaminovou, ethylaminovou, n-propylaminovou nebo izopropylami40 novou skupinu, popřípadě kyanoskupinou, karboxyskupinou, atomem fluoru, chloru nebo bromu, methoxykarbonylovou a/nebo ethoxykarbonylovou skupinou substituovanou ethenylovou, propenylovou, propenyloxylovou, butenyloxylovou, propinyloxylovou nebo butinyloxylovou skupinu, popřípadě fluorem a/nebo chlorem substituovanou methylsulfonylaminovou, ethylsulfonylaminovou, n-propylsulfonylaminovou, izopropylsulfonylami45 novou, n-butylsulfonylaminovou, izobutysulfonylaminovou, sek.-butylsulfonylaminovou, terc.-butylsulfonylaminovou, Ν,Ν-bis-methylsulfonylaminovou, N,N-bis-ethylsulfonylaminovou, N-ethylsulfonyl-N-methylsulfonylaminovou, N-acetyl-N-methylsulfonylaminovou, N-propionyl-N-methylsulfonylaminovou, N-n-butyroyl-N-methylsulfonylaminovou, N-izobutyroyl-N-methylsulfonylaminovou, N-acetyl-N-ethylsulfonyl50 aminovou, n-propionyl-N-ethylsulfonylaminovou, N-n-butyroyl-N-ethylsulfonylaminovou nebo N-izobutyroyl-N-ethylsulfonylaminovou skupinu, nebo popřípadě kyanoskupinou, atomem fluoru, chloru nebo bromu, methylovou, ethylovou, n-propylovou, izopropylovou, n-butylovou, izobutylovou, sek.-butylovou, terc.-butylovou, trifluormethylovou, methoxylovou, ethoxylovou, n-propoxylovou, izopropoxylovou, difluor55 methoxylovou nebo trifluormethoxylovou skupinou substituovanou N-fenylkarbonyl-N-21 CZ 298793 B6 methylsulfonylaminovou, N-fenylkarbonyl-N-ethylsulfonylaminovou, N-thienylkarbonyl-N-methylsulfonylaminovou nebo N-thienylkarbonyl-N-ethylsulfonylaminovou skupinu,5 označované jako účinné látky skupiny 1 a (b) účinné množství alespoň jednoho N-arylsulfonylamino(thio)karbonyl-triazolin(thi)onu obecného vzorce II, ve kterém ío Q2 a Q3 značí atom kyslíku nebo síry,R6 značí popřípadě atomem fluoru nebo chloru, methoxyskupinou nebo ethoxyskupinou substituovanou methylovou, ethylovou, methoxylovou, ethoxylovou nebo cyklopropylovou skupinu,R7 značí atom fluoru nebo chloru, popřípadě atomem fluoru nebo chloru, methoxylovou nebo ethoxylovou skupinou substituovanou methylovou, ethylovou, n-propylovou, izopropylovou, methoxylovou, ethoxylovou, n-propoxylovou, izopropoxylovou, methylthio-, ethylthio-, n-propylthio, izopropylthio-, methylaminovou, ethylaminovou, n-propylaminovou,20 izopropylaminovou, n-butylaminovou, nebo izobutylaminovou skupinu, nebo dimethylaminovou, propenylthio-, propinylthio- nebo cyklopropylovou skupinu,R8 značí atom fluoru, chloru nebo bromu, popřípadě atomem fluoru nebo chloru, methoxyskupinou nebo ethoxyskupinou substituovanou methylovou, ethylovou, n-propylovou, izo25 propylovou, methoxylovou, ethoxylovou, n-propoxylovou, izopropoxylovou, methoxykarbonylovou, ethoxykarbonylovou, n-propoxykarbonylovou, izopropoxykarbonylovou, methylthio-, ethylthio-, η-propylthio-, izopropylthio-, methylsulfinylovou, ethylsulfínylovou, n-propylsulfínylovou, izopropylsulfínylovou, methylsulfonylovou, ethylsulfonylovou, n-propylsulfonylovou, izopropylsulfonylovou, methylaminovou, ethylaminovou, n30 propylaminovou, izopropylaminovou nebo cyklopropylovou skupinu aR9 značí vodíkový atom, nitroskupinu, kyanoskupinu, atom fluoru, chloru nebo bromu, popřípadě atomem fluoru nebo chloru, methoxyskupinou nebo ethoxyskupinou substituovanou methylovou, ethylovou, n-propylovou, izopropylovou, methoxylovou, ethoxylovou, n35 propoxylovou, izopropoxylovou, methoxykarbonylovou, ethoxykarbonylovou, n-propoxykarbonylovou, izopropoxykarbonylovou, methylthio-, ethylthio-, η-propylthio-, izopropylthio, methylsulfinylovou, ethylsulfínylovou, n-propylsulfínylovou, izopropyl sulfínylovou, methylsulfonylovou, ethylsulfonylovou, n-propylsulfonylovou, izopropylsulfonylovou nebo cyklopropylovou skupinu, a/nebo solí sloučeniny obecného vzorce II, označované jako účinné látky skupiny 2.
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| DE19845407B4 (de) * | 1998-10-02 | 2012-06-28 | Arysta LifeScience North America Corp.(n.d.Ges.d.Staates Californien) | Selektive Herbizide auf Basis eines substituierten Phenylsulfonylaminocarbonyl-triazolinons |
| WO2001022819A1 (de) * | 1999-09-30 | 2001-04-05 | Bayer Aktiengesellschaft | Selektive herbizide auf basis von n-aryl-triazolin(thi)onen |
| DE19962017A1 (de) * | 1999-09-30 | 2001-04-05 | Bayer Ag | Selektive Herbizide auf Basis von N-Aryl-triazolin(thi)onen |
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| HUE056716T2 (hu) | 2016-09-30 | 2022-03-28 | Vertex Pharma | Cisztás firbrózis transzmembrán konduktancia regulátor modulátora, gyógyszerészeti készítmények, kezelési eljárások, és eljárások a modulátor elõállítására |
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| BR112019025801A2 (pt) | 2017-06-08 | 2020-07-07 | Vertex Pharmaceuticals Incorporated | métodos de tratamento para fibrose cística |
| WO2019018395A1 (en) | 2017-07-17 | 2019-01-24 | Vertex Pharmaceuticals Incorporated | METHODS OF TREATING CYSTIC FIBROSIS |
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| US10654829B2 (en) | 2017-10-19 | 2020-05-19 | Vertex Pharmaceuticals Incorporated | Crystalline forms and compositions of CFTR modulators |
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1999
- 1999-01-12 PL PL341903A patent/PL196504B1/pl not_active IP Right Cessation
- 1999-01-12 SI SI9930180T patent/SI1049376T1/xx unknown
- 1999-01-12 DE DE59903090T patent/DE59903090D1/de not_active Expired - Lifetime
- 1999-01-12 CA CA002319225A patent/CA2319225C/en not_active Expired - Fee Related
- 1999-01-12 AU AU26165/99A patent/AU735402B2/en not_active Ceased
- 1999-01-12 HU HU0100565A patent/HUP0100565A3/hu unknown
- 1999-01-12 AT AT99906118T patent/ATE226016T1/de active
- 1999-01-12 DK DK99906118T patent/DK1049376T3/da active
- 1999-01-12 SK SK1100-2000A patent/SK285006B6/sk not_active IP Right Cessation
- 1999-01-12 CZ CZ20002715A patent/CZ298793B6/cs not_active IP Right Cessation
- 1999-01-12 TR TR2000/02114T patent/TR200002114T2/xx unknown
- 1999-01-12 WO PCT/EP1999/000130 patent/WO1999037153A1/de active IP Right Grant
- 1999-01-12 CN CNB998023418A patent/CN100438763C/zh not_active Expired - Fee Related
- 1999-01-12 EP EP99906118A patent/EP1049376B1/de not_active Expired - Lifetime
- 1999-01-12 RU RU2000122362/04A patent/RU2228032C2/ru not_active IP Right Cessation
- 1999-01-12 US US09/600,576 patent/US6297192B1/en not_active Expired - Fee Related
- 1999-01-12 NZ NZ505899A patent/NZ505899A/en unknown
- 1999-01-12 ES ES99906118T patent/ES2182486T3/es not_active Expired - Lifetime
- 1999-12-01 UA UA2000084985A patent/UA67766C2/uk unknown
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| WO1998012923A1 (de) * | 1996-09-23 | 1998-04-02 | Bayer Aktiengesellschaft | Selektive herbizide auf basis von arylsulfonylaminocarbonyltriazolinonen |
Also Published As
| Publication number | Publication date |
|---|---|
| CN100438763C (zh) | 2008-12-03 |
| SK11002000A3 (sk) | 2001-03-12 |
| CA2319225C (en) | 2008-08-26 |
| DK1049376T3 (da) | 2003-02-17 |
| HUP0100565A2 (hu) | 2001-06-28 |
| PL196504B1 (pl) | 2008-01-31 |
| AU2616599A (en) | 1999-08-09 |
| AU735402B2 (en) | 2001-07-05 |
| EP1049376A1 (de) | 2000-11-08 |
| ES2182486T3 (es) | 2003-03-01 |
| PL341903A1 (en) | 2001-05-07 |
| RU2228032C2 (ru) | 2004-05-10 |
| SI1049376T1 (en) | 2003-06-30 |
| ATE226016T1 (de) | 2002-11-15 |
| CA2319225A1 (en) | 1999-07-29 |
| CN1288353A (zh) | 2001-03-21 |
| NZ505899A (en) | 2002-06-28 |
| US6297192B1 (en) | 2001-10-02 |
| UA67766C2 (uk) | 2004-07-15 |
| CZ20002715A3 (cs) | 2000-11-15 |
| DE19802697A1 (de) | 1999-07-29 |
| TR200002114T2 (tr) | 2000-12-21 |
| HUP0100565A3 (en) | 2002-12-28 |
| EP1049376B1 (de) | 2002-10-16 |
| WO1999037153A1 (de) | 1999-07-29 |
| SK285006B6 (sk) | 2006-04-06 |
| DE59903090D1 (de) | 2002-11-21 |
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Legal Events
| Date | Code | Title | Description |
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| MM4A | Patent lapsed due to non-payment of fee |
Effective date: 20120112 |