CH623458A5 - - Google Patents
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- Publication number
- CH623458A5 CH623458A5 CH1264975A CH1264975A CH623458A5 CH 623458 A5 CH623458 A5 CH 623458A5 CH 1264975 A CH1264975 A CH 1264975A CH 1264975 A CH1264975 A CH 1264975A CH 623458 A5 CH623458 A5 CH 623458A5
- Authority
- CH
- Switzerland
- Prior art keywords
- ethyl
- methyl
- methylthiocarbonyl
- formula
- compounds
- Prior art date
Links
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 70
- 150000001875 compounds Chemical class 0.000 claims description 43
- 239000000460 chlorine Chemical group 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 241000233866 Fungi Species 0.000 claims description 14
- -1 halogen anion Chemical class 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 229910052801 chlorine Chemical group 0.000 claims description 9
- UFFBMTHBGFGIHF-UHFFFAOYSA-N (2,6-Me2C6H3)NH2 Natural products CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 230000003641 microbiacidal effect Effects 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 230000003032 phytopathogenic effect Effects 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
- 241000251730 Chondrichthyes Species 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- FHMPFSKGDPKPDJ-UHFFFAOYSA-N 2,3,6-trimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1C FHMPFSKGDPKPDJ-UHFFFAOYSA-N 0.000 claims 1
- WOJKWPVCSVZMBP-UHFFFAOYSA-N 2-methoxy-n-(3-sulfanylidenebutan-2-yl)-n-(2,3,6-trimethylphenyl)acetamide Chemical compound COCC(=O)N(C(C)C(C)=S)C1=C(C)C=CC(C)=C1C WOJKWPVCSVZMBP-UHFFFAOYSA-N 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- 239000004480 active ingredient Substances 0.000 description 24
- 239000000126 substance Substances 0.000 description 11
- 239000013543 active substance Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 240000003768 Solanum lycopersicum Species 0.000 description 9
- 239000004563 wettable powder Substances 0.000 description 9
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- 235000019198 oils Nutrition 0.000 description 8
- 239000002689 soil Substances 0.000 description 8
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 7
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000005995 Aluminium silicate Substances 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
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- 239000008187 granular material Substances 0.000 description 6
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 6
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 235000019993 champagne Nutrition 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 4
- 230000000855 fungicidal effect Effects 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 240000005979 Hordeum vulgare Species 0.000 description 3
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 3
- 241000233622 Phytophthora infestans Species 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 244000038559 crop plants Species 0.000 description 3
- 238000005520 cutting process Methods 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 229940124561 microbicide Drugs 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 235000010777 Arachis hypogaea Nutrition 0.000 description 2
- 235000004535 Avena sterilis Nutrition 0.000 description 2
- 241001647031 Avena sterilis Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 240000008067 Cucumis sativus Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 206010017533 Fungal infection Diseases 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- 208000031888 Mycoses Diseases 0.000 description 2
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- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 241000233639 Pythium Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
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- 239000000417 fungicide Substances 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000000913 palmityl 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])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 2
- 235000020232 peanut Nutrition 0.000 description 2
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
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- SRAWNDFHGTVUNZ-UHFFFAOYSA-M sodium;3,6-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(CCCC)=CC2=CC(CCCC)=CC=C21 SRAWNDFHGTVUNZ-UHFFFAOYSA-M 0.000 description 2
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound 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 description 2
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- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
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- LLKFNPUXQZHIAE-UHFFFAOYSA-N 5-(3-aminopropyl)-8-bromo-3-methyl-2h-pyrazolo[4,3-c]quinolin-4-one Chemical compound O=C1N(CCCN)C2=CC=C(Br)C=C2C2=C1C(C)=NN2 LLKFNPUXQZHIAE-UHFFFAOYSA-N 0.000 description 1
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- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
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- 239000003085 diluting agent Substances 0.000 description 1
- MZGNSEAPZQGJRB-UHFFFAOYSA-N dimethyldithiocarbamic acid Chemical compound CN(C)C(S)=S MZGNSEAPZQGJRB-UHFFFAOYSA-N 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 1
- 239000002855 microbicide agent Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- QNVKMXGRFVLMBM-UHFFFAOYSA-N n-chloro-n-phenylacetamide Chemical class CC(=O)N(Cl)C1=CC=CC=C1 QNVKMXGRFVLMBM-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
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000015136 pumpkin Nutrition 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003738 xylenes Chemical class 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/46—N-acyl derivatives
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (33)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1264975A CH623458A5 (el) | 1975-09-30 | 1975-09-30 | |
| PT65642A PT65642B (en) | 1975-09-30 | 1976-09-24 | Process for preparing of microbicidal compositions |
| US05/726,321 US4075349A (en) | 1975-09-30 | 1976-09-24 | Microbicidal compositions |
| DE2643403A DE2643403C2 (de) | 1975-09-30 | 1976-09-27 | Thiocarbonsäurederivate, Verfahren zu deren Herstellung und diese enthaltende Mittel |
| AR264878A AR216061A1 (es) | 1975-09-30 | 1976-09-28 | Derivados de n-(1'-alquiltiocarbonil-etil)-n-acetil anilina mono-o poli-sustituida,procedimiento para prepararlos y composiciones que contienen dicho derivado |
| LU75894A LU75894A1 (el) | 1975-09-30 | 1976-09-28 | |
| SE7610727A SE432762B (sv) | 1975-09-30 | 1976-09-28 | Vissa fungicida n-acylderivat av alfa-anilino-propion-syratioestrar samt anvendning derav som fungicider |
| PH18947A PH12952A (en) | 1975-09-30 | 1976-09-28 | Microbicidal compositions |
| EG593/76A EG12286A (en) | 1975-09-30 | 1976-09-28 | Microbicidal compositions |
| BG034300A BG27520A3 (en) | 1975-09-30 | 1976-09-28 | Fungicide means |
| IL50560A IL50560A (en) | 1975-09-30 | 1976-09-28 | N-(1-alkylthiocarbonylacetyl)-n-substituted acetyl-aniline derivatives,their manufacture and fungicidal and bactericidal compositions containing them |
| FR7629113A FR2326416A1 (fr) | 1975-09-30 | 1976-09-28 | Nouveaux derives de l'aniline, procede pour leur preparation et application en tant qu'agents microbicides |
| CA262,212A CA1073922A (en) | 1975-09-30 | 1976-09-28 | Microbicidal acylated thiopropionyl anilines |
| BR7606451A BR7606451A (pt) | 1975-09-30 | 1976-09-28 | Compostos organicos,processo para sua preparacao,composicao para o combate de fungos e bacterias e sua aplicacao |
| DD7600195023A DD128534A5 (de) | 1975-09-30 | 1976-09-28 | Mikrobizide mittel |
| ZA00765838A ZA765838B (en) | 1975-09-30 | 1976-09-29 | Microbicidal compositions |
| ES451934A ES451934A1 (es) | 1975-09-30 | 1976-09-29 | Procedimiento para la preparacion de n-derivados de anilinasde actividad microbicida. |
| BE171032A BE846696A (fr) | 1975-09-30 | 1976-09-29 | Nouveaux derives de l'aniline, procede pour leur preparation et application en tant qu'agents microbicides |
| NL7610791A NL7610791A (nl) | 1975-09-30 | 1976-09-29 | Microbicide middelen. |
| HU76CI1688A HU175067B (hu) | 1975-09-30 | 1976-09-29 | Fungicidnye kompozicii soderzhahhie proizvodnye aniliny i sposob poluchenija aktivnykh agentov |
| DK438676A DK149363C (da) | 1975-09-30 | 1976-09-29 | N-(1'-alkylthiocarbonyl-ethyl)-n-acetyl-anilinderivater til anvendelse til bekaempelse af fytopatogene svampe samt middel og fremgangsmaade til bekaempelse af fytopatogene svampe |
| AU18218/76A AU503965B2 (en) | 1975-09-30 | 1976-09-29 | Substituted anilides |
| IE2149/76A IE43631B1 (en) | 1975-09-30 | 1976-09-29 | Anilides containing a thiocarboxylic ester group having microbicidal activity |
| IT2780376A IT1123062B (it) | 1975-09-30 | 1976-09-29 | Prodotti microbicidi e procedimento per combattere funghi fitopatogeni oppure per impedire un attacco da parte di funghi mediante trattamento di piante oppure di parti di piante con detti prodotti |
| AT722276A AT347183B (de) | 1975-09-30 | 1976-09-29 | Mikrobizides mittel |
| GB40476/76A GB1524584A (en) | 1975-09-30 | 1976-09-29 | Anilides containing a thiocarboxylic ester group having microbicidal activity |
| NZ182185A NZ182185A (en) | 1975-09-30 | 1976-09-29 | Aniline derivatives and fungicidal compositions |
| PL1976192721A PL103856B1 (pl) | 1975-09-30 | 1976-09-29 | Srodek do zwalczania grzybow i bakterii |
| JP51117898A JPS5943458B2 (ja) | 1975-09-30 | 1976-09-30 | アニリン誘導体及びその製法並びに該化合物を有効成分とする微生物防除剤 |
| SU762407098A SU692534A3 (ru) | 1975-09-30 | 1976-09-30 | Фунгицидное средство |
| CS766330A CS194780B2 (en) | 1975-09-30 | 1976-09-30 | Fungicide and process for preparing effective component thereof |
| CH614080A CH632491A5 (de) | 1975-09-30 | 1980-08-14 | Verfahren zur herstellung von mikrobiziden wirkstoffen und ihre verwendung. |
| CH466481A CH634047A5 (de) | 1975-09-30 | 1981-07-16 | Verfahren zur herstellung von mikrobiziden wirkstoffen und ihre verwendung. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1264975A CH623458A5 (el) | 1975-09-30 | 1975-09-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH623458A5 true CH623458A5 (el) | 1981-06-15 |
Family
ID=4385084
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1264975A CH623458A5 (el) | 1975-09-30 | 1975-09-30 | |
| CH614080A CH632491A5 (de) | 1975-09-30 | 1980-08-14 | Verfahren zur herstellung von mikrobiziden wirkstoffen und ihre verwendung. |
| CH466481A CH634047A5 (de) | 1975-09-30 | 1981-07-16 | Verfahren zur herstellung von mikrobiziden wirkstoffen und ihre verwendung. |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH614080A CH632491A5 (de) | 1975-09-30 | 1980-08-14 | Verfahren zur herstellung von mikrobiziden wirkstoffen und ihre verwendung. |
| CH466481A CH634047A5 (de) | 1975-09-30 | 1981-07-16 | Verfahren zur herstellung von mikrobiziden wirkstoffen und ihre verwendung. |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US4075349A (el) |
| JP (1) | JPS5943458B2 (el) |
| AR (1) | AR216061A1 (el) |
| AT (1) | AT347183B (el) |
| AU (1) | AU503965B2 (el) |
| BE (1) | BE846696A (el) |
| BG (1) | BG27520A3 (el) |
| BR (1) | BR7606451A (el) |
| CA (1) | CA1073922A (el) |
| CH (3) | CH623458A5 (el) |
| CS (1) | CS194780B2 (el) |
| DD (1) | DD128534A5 (el) |
| DE (1) | DE2643403C2 (el) |
| DK (1) | DK149363C (el) |
| EG (1) | EG12286A (el) |
| ES (1) | ES451934A1 (el) |
| FR (1) | FR2326416A1 (el) |
| GB (1) | GB1524584A (el) |
| HU (1) | HU175067B (el) |
| IE (1) | IE43631B1 (el) |
| IL (1) | IL50560A (el) |
| LU (1) | LU75894A1 (el) |
| NL (1) | NL7610791A (el) |
| NZ (1) | NZ182185A (el) |
| PH (1) | PH12952A (el) |
| PL (1) | PL103856B1 (el) |
| PT (1) | PT65642B (el) |
| SE (1) | SE432762B (el) |
| SU (1) | SU692534A3 (el) |
| ZA (1) | ZA765838B (el) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| OA04979A (fr) * | 1974-04-09 | 1980-11-30 | Ciba Geigy | Nouveaux dérivés de l'aniline utiles comme agents microbicides et leur procédé de préparation. |
| US4206228A (en) * | 1974-04-09 | 1980-06-03 | Ciba-Geigy Corporation | Microbicidal aniline derivatives |
| IL52928A0 (en) * | 1976-09-17 | 1977-11-30 | Ciba Geigy Ag | New aniline derivatives their preparation and pesticidal compositions containing them |
| CH627343A5 (en) * | 1977-03-28 | 1982-01-15 | Ciba Geigy Ag | Microbicide |
| DE2915026A1 (de) * | 1979-04-12 | 1980-10-30 | Bayer Ag | N,n-disubstituierte ethylglycin (thiol)ester, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
| ES8104796A1 (es) * | 1979-07-25 | 1981-05-16 | Hoechst Ag | Procedimiento para la preparacion de anilidas de acido tio- glicolico, fungicidas |
| MA19215A1 (fr) * | 1980-07-25 | 1982-04-01 | Ciba Geigy Ag | Nouveaux derives arylamines,procede pour leur fabrication et utilisation en tant que microbicides . |
| FR2513993A1 (fr) * | 1981-10-06 | 1983-04-08 | Rhone Poulenc Agrochimie | Nouveaux fongicides homologues des n-phenyl alaninates et leur procede de preparation et leur application |
| DE3436523A1 (de) * | 1984-10-05 | 1986-04-10 | Heinrich Hermann Gmbh + Co, 7000 Stuttgart | Handspendegeraet zum spenden und andruecken von haftetiketten |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3778460A (en) * | 1967-02-27 | 1973-12-11 | Ethyl Corp | Hydrocarbyl-hydroxyphenyl dithiocarbamates and their use as antioxidants |
| US3712805A (en) * | 1967-12-28 | 1973-01-23 | Shell Oil Co | Weed control employing n,n-disubstituted amino acid herbicides |
| US3488377A (en) * | 1968-01-03 | 1970-01-06 | Velsicol Chemical Corp | 1-(phenyl)-1-loweralkylthiocarbonyloxy-3-ureas |
| US3830829A (en) * | 1971-06-01 | 1974-08-20 | Monsanto Co | Chlorophenoxyalkyl anilides |
| US3832383A (en) * | 1971-06-01 | 1974-08-27 | Monsanto Co | Herbicidal acyloxyalkyl anilides |
| BE794108A (fr) * | 1972-01-18 | 1973-07-16 | Shell Int Research | Nouveaux derives d'amino-acides disubstitues a l'azote |
| SE397191B (sv) * | 1972-10-13 | 1977-10-24 | Ciba Geigy Ag | N-(1'-alkoxikarbonyl-etyl)-n-haloacetyl-2,6-dialkylaniliner till anvendning som fungicid |
-
1975
- 1975-09-30 CH CH1264975A patent/CH623458A5/de not_active IP Right Cessation
-
1976
- 1976-09-24 PT PT65642A patent/PT65642B/pt unknown
- 1976-09-24 US US05/726,321 patent/US4075349A/en not_active Expired - Lifetime
- 1976-09-27 DE DE2643403A patent/DE2643403C2/de not_active Expired
- 1976-09-28 PH PH18947A patent/PH12952A/en unknown
- 1976-09-28 FR FR7629113A patent/FR2326416A1/fr active Granted
- 1976-09-28 CA CA262,212A patent/CA1073922A/en not_active Expired
- 1976-09-28 BG BG034300A patent/BG27520A3/xx unknown
- 1976-09-28 SE SE7610727A patent/SE432762B/xx not_active IP Right Cessation
- 1976-09-28 DD DD7600195023A patent/DD128534A5/xx unknown
- 1976-09-28 LU LU75894A patent/LU75894A1/xx unknown
- 1976-09-28 EG EG593/76A patent/EG12286A/xx active
- 1976-09-28 BR BR7606451A patent/BR7606451A/pt unknown
- 1976-09-28 IL IL50560A patent/IL50560A/xx unknown
- 1976-09-28 AR AR264878A patent/AR216061A1/es active
- 1976-09-29 NZ NZ182185A patent/NZ182185A/xx unknown
- 1976-09-29 ES ES451934A patent/ES451934A1/es not_active Expired
- 1976-09-29 ZA ZA00765838A patent/ZA765838B/xx unknown
- 1976-09-29 AT AT722276A patent/AT347183B/de active
- 1976-09-29 PL PL1976192721A patent/PL103856B1/pl not_active IP Right Cessation
- 1976-09-29 AU AU18218/76A patent/AU503965B2/en not_active Expired
- 1976-09-29 IE IE2149/76A patent/IE43631B1/en unknown
- 1976-09-29 NL NL7610791A patent/NL7610791A/xx not_active Application Discontinuation
- 1976-09-29 HU HU76CI1688A patent/HU175067B/hu not_active IP Right Cessation
- 1976-09-29 BE BE171032A patent/BE846696A/xx not_active IP Right Cessation
- 1976-09-29 GB GB40476/76A patent/GB1524584A/en not_active Expired
- 1976-09-29 DK DK438676A patent/DK149363C/da not_active IP Right Cessation
- 1976-09-30 CS CS766330A patent/CS194780B2/cs unknown
- 1976-09-30 JP JP51117898A patent/JPS5943458B2/ja not_active Expired
- 1976-09-30 SU SU762407098A patent/SU692534A3/ru active
-
1980
- 1980-08-14 CH CH614080A patent/CH632491A5/de not_active IP Right Cessation
-
1981
- 1981-07-16 CH CH466481A patent/CH634047A5/de not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |