CS245782B2 - Agent for protection of culture plants against harmful effects of herbicides and production method of effective compound - Google Patents
Agent for protection of culture plants against harmful effects of herbicides and production method of effective compound Download PDFInfo
- Publication number
- CS245782B2 CS245782B2 CS833107A CS310783A CS245782B2 CS 245782 B2 CS245782 B2 CS 245782B2 CS 833107 A CS833107 A CS 833107A CS 310783 A CS310783 A CS 310783A CS 245782 B2 CS245782 B2 CS 245782B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- group
- hydrogen
- formula
- carbon atoms
- alkyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 101
- 239000004009 herbicide Substances 0.000 title claims description 82
- 230000009931 harmful effect Effects 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000003795 chemical substances by application Substances 0.000 title description 5
- -1 R 5 Chemical compound 0.000 claims description 67
- 239000000203 mixture Substances 0.000 claims description 61
- 229910052739 hydrogen Inorganic materials 0.000 claims description 49
- 239000001257 hydrogen Substances 0.000 claims description 49
- 125000004432 carbon atom Chemical group C* 0.000 claims description 47
- 239000002689 soil Substances 0.000 claims description 45
- 241000196324 Embryophyta Species 0.000 claims description 43
- 239000004480 active ingredient Substances 0.000 claims description 39
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 239000000460 chlorine Substances 0.000 claims description 29
- 244000038559 crop plants Species 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 239000013543 active substance Substances 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 229910052783 alkali metal Inorganic materials 0.000 claims description 11
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 10
- 150000001342 alkaline earth metals Chemical group 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 241000209140 Triticum Species 0.000 claims description 9
- 235000021307 Triticum Nutrition 0.000 claims description 9
- 230000000694 effects Effects 0.000 claims description 9
- 238000002474 experimental method Methods 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 229920003023 plastic Polymers 0.000 claims description 9
- 239000004033 plastic Substances 0.000 claims description 9
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- 238000009331 sowing Methods 0.000 claims description 8
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 150000001340 alkali metals Chemical group 0.000 claims description 7
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 7
- 235000010469 Glycine max Nutrition 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 239000004563 wettable powder Substances 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical group O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 239000006185 dispersion Substances 0.000 claims description 5
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 244000068988 Glycine max Species 0.000 claims description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 125000002015 acyclic group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 230000012010 growth Effects 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 229930195734 saturated hydrocarbon Chemical group 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 2
- 125000004848 alkoxyethyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
- 230000002786 root growth Effects 0.000 claims description 2
- 239000004576 sand Substances 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical group C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000005208 trialkylammonium group Chemical group 0.000 claims description 2
- 125000005023 xylyl group Chemical group 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 1
- 239000007900 aqueous suspension Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- ICJSJAJWTWPSBD-UHFFFAOYSA-N cloquintocet Chemical group C1=CN=C2C(OCC(=O)O)=CC=C(Cl)C2=C1 ICJSJAJWTWPSBD-UHFFFAOYSA-N 0.000 claims 1
- 238000011156 evaluation Methods 0.000 claims 1
- 238000003973 irrigation Methods 0.000 claims 1
- 230000002262 irrigation Effects 0.000 claims 1
- YLYBTZIQSIBWLI-UHFFFAOYSA-N octyl acetate Chemical compound CCCCCCCCOC(C)=O YLYBTZIQSIBWLI-UHFFFAOYSA-N 0.000 claims 1
- 239000003415 peat Substances 0.000 claims 1
- 230000000638 stimulation Effects 0.000 claims 1
- 230000002363 herbicidal effect Effects 0.000 description 61
- 239000000729 antidote Substances 0.000 description 45
- 238000000034 method Methods 0.000 description 24
- 230000001681 protective effect Effects 0.000 description 20
- 241000209094 Oryza Species 0.000 description 16
- 235000007164 Oryza sativa Nutrition 0.000 description 16
- 239000002253 acid Substances 0.000 description 16
- 235000009566 rice Nutrition 0.000 description 16
- 239000000126 substance Substances 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
- 150000002431 hydrogen Chemical class 0.000 description 13
- 238000005554 pickling Methods 0.000 description 12
- 239000008187 granular material Substances 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 239000004927 clay Substances 0.000 description 10
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 9
- 239000005995 Aluminium silicate Substances 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- 235000012211 aluminium silicate Nutrition 0.000 description 8
- 239000012141 concentrate Substances 0.000 description 8
- 235000008504 concentrate Nutrition 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 150000003248 quinolines Chemical class 0.000 description 8
- BPEXTIMJLDWDTL-UHFFFAOYSA-N 2`-Methylacetanilide Chemical compound CC(=O)NC1=CC=CC=C1C BPEXTIMJLDWDTL-UHFFFAOYSA-N 0.000 description 7
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 5
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- 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 4
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- MINGZRVPYSQHGO-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-n-phenylpropanamide Chemical compound C=1C=C(Cl)C(Cl)=CC=1N(C(=O)CC)C1=CC=CC=C1 MINGZRVPYSQHGO-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- HLWWUAGXWCWAKG-UHFFFAOYSA-N n-ethyl-1,3,5-triazin-2-amine Chemical compound CCNC1=NC=NC=N1 HLWWUAGXWCWAKG-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- KARHEVUCLSFWAH-UHFFFAOYSA-N octyl 2-(5-chloroquinolin-8-yl)oxyacetate Chemical compound C1=CN=C2C(OCC(=O)OCCCCCCCC)=CC=C(Cl)C2=C1 KARHEVUCLSFWAH-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical class CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 1
- BGRYSGVIVVUJHH-UHFFFAOYSA-N prop-2-ynyl propanoate Chemical compound CCC(=O)OCC#C BGRYSGVIVVUJHH-UHFFFAOYSA-N 0.000 description 1
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical class OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- 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
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
- C07D215/28—Alcohols; Ethers thereof with halogen atoms or nitro radicals in positions 5, 6 or 7
-
- 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
- C07D405/02—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 two hetero rings
- C07D405/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Pest Control & Pesticides (AREA)
- Toxicology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pretreatment Of Seeds And Plants (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH284182 | 1982-05-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS245782B2 true CS245782B2 (en) | 1986-10-16 |
Family
ID=4242791
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS833107A CS245782B2 (en) | 1982-05-07 | 1983-05-03 | Agent for protection of culture plants against harmful effects of herbicides and production method of effective compound |
Country Status (26)
| Country | Link |
|---|---|
| US (3) | US4902340A (ro) |
| EP (1) | EP0094349B1 (ro) |
| JP (2) | JPS58203967A (ro) |
| AR (1) | AR241407A1 (ro) |
| AT (1) | ATE103902T1 (ro) |
| AU (1) | AU575777B2 (ro) |
| BG (1) | BG61093B2 (ro) |
| BR (1) | BR8302394A (ro) |
| CA (1) | CA1218994A (ro) |
| CS (1) | CS245782B2 (ro) |
| DD (1) | DD210832A5 (ro) |
| DE (1) | DE3382743D1 (ro) |
| DK (1) | DK173071B1 (ro) |
| ES (2) | ES522141A0 (ro) |
| GB (1) | GB2120661B (ro) |
| GR (1) | GR78348B (ro) |
| HU (1) | HU190898B (ro) |
| IL (1) | IL68588A (ro) |
| KE (1) | KE3870A (ro) |
| MY (1) | MY8700859A (ro) |
| NZ (1) | NZ204151A (ro) |
| PL (1) | PL141315B1 (ro) |
| RO (1) | RO85265B (ro) |
| SU (1) | SU1658807A3 (ro) |
| UA (1) | UA5959A1 (ro) |
| ZA (1) | ZA833238B (ro) |
Families Citing this family (405)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE55993T1 (de) * | 1983-10-18 | 1990-09-15 | Ciba Geigy Ag | Verwendung von chinolinderivaten zum schuetzen von kulturpflanzen. |
| DE3404401C2 (de) * | 1984-02-08 | 1994-02-10 | Hoechst Ag | Verwendung von Aryloxy-Verbindungen als Antidots |
| EP0159287B1 (de) * | 1984-03-15 | 1989-10-11 | Ciba-Geigy Ag | Verwendung von Chinolinderivaten zum Schützen von Kulturpflanzen |
| EP0159290A1 (de) * | 1984-03-28 | 1985-10-23 | Ciba-Geigy Ag | Verwendung von Chinolinderivaten zum Schützen von Kulturpflanzen |
| EP0191736B1 (de) * | 1985-02-14 | 1991-07-17 | Ciba-Geigy Ag | Verwendung von Chinolinderivaten zum Schützen von Kulturpflanzen |
| DD261734A5 (de) | 1985-02-14 | 1988-11-09 | Ciba Geigy Ag,Ch | Verfahren zum schuetzen von kulturpflanzen |
| DE3624859A1 (de) * | 1986-07-23 | 1988-01-28 | Hoechst Ag | Neue chinolinoxy-verbindungen, verfahren zu ihrer herstellung und ihre verwendung als antidots |
| EP0258184A3 (de) * | 1986-08-13 | 1988-11-30 | Ciba-Geigy Ag | Chinolinderivate als Herbizid- antagonisten für Kulturpflanzen |
| EP0379867B1 (de) * | 1989-01-18 | 1993-12-08 | Bayer Ag | Flüssige und feste Wirkstoffe enthaltende Trägergranulate |
| EP0407341B1 (de) * | 1989-07-05 | 1995-12-06 | Ciba-Geigy Ag | Selektiv-herbizides Mittel |
| ES2151879T3 (es) * | 1990-12-21 | 2001-01-16 | Aventis Cropscience Gmbh | Mezclas de herbicidas y antidotos. |
| EP0492366B1 (de) * | 1990-12-21 | 1997-03-26 | Hoechst Schering AgrEvo GmbH | Neue 5-Chlorchinolin-8-oxyalkancarbonsäurederivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Antidots von Herbiziden |
| CA2112459A1 (en) | 1991-06-29 | 1993-01-07 | Frank Zurmuhlen | Novel mixtures of herbicides and antidotes |
| JP3804072B2 (ja) * | 1991-08-07 | 2006-08-02 | 日産化学工業株式会社 | 水性懸濁状農薬製剤 |
| EP0943240B1 (de) * | 1991-12-31 | 2001-11-14 | Aventis CropScience GmbH | Kombinationen aus Herbiziden und pflanzenschützenden Stoffen |
| AU3454193A (en) | 1992-02-21 | 1993-09-13 | Ciba-Geigy Ag | Sulfonylureas as herbicides |
| US5541148A (en) * | 1992-07-08 | 1996-07-30 | Ciba-Geigy Corporation | Selective safened herbicidal composition comprising 2-ethoxycarbonyl-3-(4,6-dimethoxypyrimidine-2-yl) oxy-pyridine and an acylsulfamoylphenyl-urea safener |
| LT3258B (en) | 1992-07-30 | 1995-05-25 | Ciba Geigy Ag | Selective herbicidic preparation and method for using thereof |
| MY109136A (en) * | 1992-07-30 | 1996-12-31 | Ciba Geigy Ag | Selective herbicidal composition |
| TW259690B (ro) | 1992-08-01 | 1995-10-11 | Hoechst Ag | |
| DE4315153A1 (de) * | 1993-05-07 | 1994-11-10 | Hoechst Schering Agrevo Gmbh | Substituierte Chinolinverbindungen, Verfahren zu deren Herstellung, diese enthaltende Mittel und deren Verwendung als Safener |
| DE4333249A1 (de) * | 1993-09-30 | 1995-04-06 | Hoechst Schering Agrevo Gmbh | Neue Mischungen aus Herbiziden und Antidots |
| EE9400262A (et) * | 1993-12-08 | 1996-02-15 | Ciba-Geigy Ag | Selektiivne herbitsiidsegu ja selle kasutamise meetod |
| EP0739164A1 (en) | 1994-01-10 | 1996-10-30 | Novartis AG | Wettable powder formulations of herbicides |
| CA2199636A1 (en) * | 1994-10-17 | 1996-04-25 | Jutta Glock | Herbicidal compositions |
| DE4440354A1 (de) | 1994-11-11 | 1996-05-15 | Hoechst Schering Agrevo Gmbh | Kombinationen aus Phenylsulfonylharnstoff-Herbiziden und Safenern |
| ES2205156T3 (es) * | 1996-03-13 | 2004-05-01 | Syngenta Participations Ag | Combinaciones herbicidas. |
| DE19638233A1 (de) * | 1996-09-19 | 1998-03-26 | Hoechst Schering Agrevo Gmbh | Kombinationen aus Sulfonylharnstoff-Herbiziden und Safenern |
| US6376424B1 (en) | 1998-01-21 | 2002-04-23 | Syngenta Crop Protection, Inc. | Herbicidal composition |
| US6342466B1 (en) | 1999-09-02 | 2002-01-29 | Clariant Finance (Bvi) Limited | Biodegradable solutions of biologically active compounds |
| WO2002000625A2 (en) * | 2000-06-28 | 2002-01-03 | Syngenta Participations Ag | Process for the preparation of quinoline derivatives |
| DE10031825A1 (de) | 2000-06-30 | 2002-01-10 | Bayer Ag | Selektive Herbizide auf Basis von Arylsulfonylaminocarbonyltriazolinonen |
| DE10036002A1 (de) | 2000-07-25 | 2002-02-14 | Aventis Cropscience Gmbh | Herbizide Mittel |
| AR031027A1 (es) * | 2000-10-23 | 2003-09-03 | Syngenta Participations Ag | Composiciones agroquimicas |
| EP2206703A1 (de) | 2008-12-30 | 2010-07-14 | Bayer CropScience AG | Pyrimidinderivate und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwachstums |
| DE10135642A1 (de) | 2001-07-21 | 2003-02-27 | Bayer Cropscience Gmbh | Herbizid-Kombinationen mit speziellen Sulfonylharnstoffen |
| DE10139465A1 (de) * | 2001-08-10 | 2003-02-20 | Bayer Cropscience Ag | Selektive Herbizide auf Basis von substituierten, cayclischen Ketoenolen und Safenern |
| DE10146590A1 (de) | 2001-09-21 | 2003-04-10 | Bayer Cropscience Ag | Selektive Herbizide auf Basis von substituierten Thien-3-yl-sulfonylamino(thio)carbonyl-triazolin(thi)onen und Safenern |
| DE10301804A1 (de) * | 2003-01-20 | 2004-07-29 | Bayer Cropscience Ag | 2,4-Dihalogen-6-(C2-C3-alkyl)-phenyl substituierte Tetramsäure-Derivate |
| DE10301806A1 (de) * | 2003-01-20 | 2004-07-29 | Bayer Cropscience Ag | Selektive Herbizide auf Basis von substituierten, cyclischen Dicarbonylverbindungen und Safenern |
| CA2515116C (en) | 2003-02-05 | 2014-01-21 | Bayer Cropscience Gmbh | Amino-1,3,5-triazines n-substituted with chiral bicyclic radicals, process for their preparation, compositions thereof, and their use as herbicides and plant growth regulators |
| DE10311300A1 (de) * | 2003-03-14 | 2004-09-23 | Bayer Cropscience Ag | 2,4,6-Phenylsubstituierte cyclische Ketoenole |
| DE10326386A1 (de) | 2003-06-12 | 2004-12-30 | Bayer Cropscience Ag | N-Heterocyclyl-phenylsubstituierte cyclische Ketoenole |
| DE10331675A1 (de) | 2003-07-14 | 2005-02-10 | Bayer Cropscience Ag | Hetarylsubstituierte Pyrazolidindion-Derivate |
| DE10337496A1 (de) | 2003-08-14 | 2005-04-14 | Bayer Cropscience Ag | 4-Biphenylsubstituierte-4-substituierte-pyrazolidin-3,5-dione |
| DE10337497A1 (de) | 2003-08-14 | 2005-03-10 | Bayer Cropscience Ag | 4-Biphenylsubstituierte-Pyrazolidin-3,5-dion-Derivate |
| DE10351647A1 (de) * | 2003-11-05 | 2005-06-09 | Bayer Cropscience Ag | 2-Halogen-6-alkyl-phenyl substituierte Tetramsäure-Derivate |
| BRPI0416669B1 (pt) * | 2003-11-17 | 2018-11-21 | Syngenta Participations Ag | concentrados emulsificáveis contendo adjuvantes, composição pesticida, e método para o controle seletivo de ervasdaninhas em plantações de vegetais úteis |
| DE10354628A1 (de) | 2003-11-22 | 2005-06-16 | Bayer Cropscience Ag | 2-Ethyl-4,6-dimethyl-phenyl-substituierte Tetramsäure-Derivate |
| DE10354629A1 (de) | 2003-11-22 | 2005-06-30 | Bayer Cropscience Ag | 2-Ethyl-4,6-dimethyl-phenyl substituierte spirocyclische Tetramsäure-Derivate |
| DE102004011007A1 (de) | 2004-03-06 | 2005-09-22 | Bayer Cropscience Ag | Suspensionskonzentrate auf Ölbasis |
| DE102004014620A1 (de) | 2004-03-25 | 2005-10-06 | Bayer Cropscience Ag | 2,4,6-phenylsubstituierte cyclische Ketoenole |
| AR048441A1 (es) | 2004-03-26 | 2006-04-26 | Syngenta Participations Ag | Una combinacion herbicida |
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| US4284566A (en) * | 1979-01-04 | 1981-08-18 | Ciba-Geigy Corporation | Herbicidal α-[4-trifluoromethylphenoxy)-propionic acid γ-butyrolactone ester and thioester |
| MA19709A1 (fr) * | 1982-02-17 | 1983-10-01 | Ciba Geigy Ag | Application de derives de quinoleine a la protection des plantes cultivees . |
| ATE55993T1 (de) * | 1983-10-18 | 1990-09-15 | Ciba Geigy Ag | Verwendung von chinolinderivaten zum schuetzen von kulturpflanzen. |
| DE3404401C2 (de) * | 1984-02-08 | 1994-02-10 | Hoechst Ag | Verwendung von Aryloxy-Verbindungen als Antidots |
| EP0159287B1 (de) * | 1984-03-15 | 1989-10-11 | Ciba-Geigy Ag | Verwendung von Chinolinderivaten zum Schützen von Kulturpflanzen |
| EP0159290A1 (de) * | 1984-03-28 | 1985-10-23 | Ciba-Geigy Ag | Verwendung von Chinolinderivaten zum Schützen von Kulturpflanzen |
| EP0191736B1 (de) * | 1985-02-14 | 1991-07-17 | Ciba-Geigy Ag | Verwendung von Chinolinderivaten zum Schützen von Kulturpflanzen |
| EP0258184A3 (de) * | 1986-08-13 | 1988-11-30 | Ciba-Geigy Ag | Chinolinderivate als Herbizid- antagonisten für Kulturpflanzen |
-
1983
- 1983-05-02 DE DE83810186T patent/DE3382743D1/de not_active Expired - Lifetime
- 1983-05-02 AT AT83810186T patent/ATE103902T1/de not_active IP Right Cessation
- 1983-05-02 EP EP83810186A patent/EP0094349B1/de not_active Expired - Lifetime
- 1983-05-03 CS CS833107A patent/CS245782B2/cs unknown
- 1983-05-03 GB GB08311973A patent/GB2120661B/en not_active Expired
- 1983-05-05 RO RO110868A patent/RO85265B/ro unknown
- 1983-05-05 AR AR83292944A patent/AR241407A1/es active
- 1983-05-05 IL IL68588A patent/IL68588A/xx not_active IP Right Cessation
- 1983-05-05 GR GR71318A patent/GR78348B/el unknown
- 1983-05-05 DD DD83250660A patent/DD210832A5/de not_active IP Right Cessation
- 1983-05-06 UA UA3592351A patent/UA5959A1/uk unknown
- 1983-05-06 BR BR8302394A patent/BR8302394A/pt not_active IP Right Cessation
- 1983-05-06 ZA ZA833238A patent/ZA833238B/xx unknown
- 1983-05-06 PL PL1983241841A patent/PL141315B1/pl unknown
- 1983-05-06 AU AU14329/83A patent/AU575777B2/en not_active Expired
- 1983-05-06 SU SU833592351A patent/SU1658807A3/ru active
- 1983-05-06 HU HU831572A patent/HU190898B/hu unknown
- 1983-05-06 NZ NZ204151A patent/NZ204151A/en unknown
- 1983-05-06 CA CA000427668A patent/CA1218994A/en not_active Expired
- 1983-05-06 ES ES522141A patent/ES522141A0/es active Granted
- 1983-05-06 DK DK198302040A patent/DK173071B1/da active Protection Beyond IP Right Term
- 1983-05-07 JP JP58079991A patent/JPS58203967A/ja active Granted
-
1984
- 1984-04-12 JP JP59073840A patent/JPH0753642B2/ja not_active Expired - Lifetime
- 1984-09-17 ES ES536425A patent/ES8607244A1/es not_active Expired
-
1986
- 1986-05-27 US US06/868,372 patent/US4902340A/en not_active Expired - Lifetime
-
1987
- 1987-12-30 MY MY859/87A patent/MY8700859A/xx unknown
-
1989
- 1989-03-09 KE KE3870A patent/KE3870A/xx unknown
- 1989-04-14 US US07/338,830 patent/US5023333A/en not_active Expired - Fee Related
-
1991
- 1991-02-05 US US07/651,119 patent/US5102445A/en not_active Expired - Lifetime
-
1992
- 1992-06-15 BG BG096474A patent/BG61093B2/bg unknown
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