CZ293561B6 - Derivát kyseliny fenyloctové, způsob přípravy těchto sloučenin, meziprodukt, prostředek s jeho obsahem a způsob potlačování živočišných škůdců nebo škodlivých hub - Google Patents
Derivát kyseliny fenyloctové, způsob přípravy těchto sloučenin, meziprodukt, prostředek s jeho obsahem a způsob potlačování živočišných škůdců nebo škodlivých hub Download PDFInfo
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- CZ293561B6 CZ293561B6 CZ19981243A CZ124398A CZ293561B6 CZ 293561 B6 CZ293561 B6 CZ 293561B6 CZ 19981243 A CZ19981243 A CZ 19981243A CZ 124398 A CZ124398 A CZ 124398A CZ 293561 B6 CZ293561 B6 CZ 293561B6
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- 238000000034 method Methods 0.000 title claims abstract description 22
- 241000607479 Yersinia pestis Species 0.000 title claims abstract description 21
- 241000233866 Fungi Species 0.000 title claims abstract description 20
- 241001465754 Metazoa Species 0.000 title claims abstract description 15
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 title claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000003795 chemical substances by application Substances 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 3091
- 238000002360 preparation method Methods 0.000 claims abstract description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 944
- -1 cyano, nitro, hydroxy, mercapto, amino, carboxyl Chemical group 0.000 claims description 324
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 303
- 125000001072 heteroaryl group Chemical group 0.000 claims description 47
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 30
- 101150065749 Churc1 gene Proteins 0.000 claims description 27
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 26
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 25
- 102100038239 Protein Churchill Human genes 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 229910052717 sulfur Inorganic materials 0.000 claims description 23
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 22
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 125000004104 aryloxy group Chemical group 0.000 claims description 20
- 125000004122 cyclic group Chemical group 0.000 claims description 20
- 229910052757 nitrogen Chemical group 0.000 claims description 20
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 19
- 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 18
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 16
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 16
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 16
- 125000004434 sulfur atom Chemical group 0.000 claims description 16
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 15
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 14
- 125000005110 aryl thio group Chemical group 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 10
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 239000011593 sulfur Chemical group 0.000 claims description 7
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
- 241000244206 Nematoda Species 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 5
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 125000004454 (C1-C6) alkoxycarbonyl 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
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 241000238631 Hexapoda Species 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 125000006725 C1-C10 alkenyl group Chemical group 0.000 claims description 2
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 2
- 241000239290 Araneae Species 0.000 claims 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 32
- 239000004480 active ingredient Substances 0.000 description 22
- 239000000460 chlorine Substances 0.000 description 22
- 241000196324 Embryophyta Species 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 239000000243 solution Substances 0.000 description 17
- 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 description 14
- 239000013543 active substance Substances 0.000 description 14
- 239000003921 oil Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 13
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 13
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 13
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 13
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 13
- 125000004510 1,3,4-oxadiazol-5-yl group Chemical group O1C=NN=C1* 0.000 description 12
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 description 12
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 description 11
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 description 11
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- 239000003995 emulsifying agent Substances 0.000 description 8
- 239000000417 fungicide Substances 0.000 description 8
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 241000209140 Triticum Species 0.000 description 6
- 235000021307 Triticum Nutrition 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 125000006163 5-membered heteroaryl group Chemical group 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 235000013339 cereals Nutrition 0.000 description 5
- 238000010410 dusting Methods 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000006072 paste Substances 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 235000013311 vegetables Nutrition 0.000 description 4
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical class CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- SRLJDWSQVVTLOJ-UHFFFAOYSA-N CC(=NOC)C(=NOC)C(=NOCC1=CC=CC=C1C(=NOC)OC(=O)C)C Chemical compound CC(=NOC)C(=NOC)C(=NOCC1=CC=CC=C1C(=NOC)OC(=O)C)C SRLJDWSQVVTLOJ-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
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- 229910052801 chlorine Inorganic materials 0.000 description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
- 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 3
- 150000002576 ketones Chemical class 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
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- 239000002689 soil Substances 0.000 description 3
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- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
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- ZVJBPHMCBRHVEV-GQCTYLIASA-N (2e)-2-hydroxyiminopentan-3-one Chemical compound CCC(=O)C(\C)=N\O ZVJBPHMCBRHVEV-GQCTYLIASA-N 0.000 description 2
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 description 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- FKQZCEPTQFPURM-UHFFFAOYSA-N 2-hydroxyimino-4-methoxyiminopentan-3-one Chemical compound CON=C(C)C(=O)C(C)=NO FKQZCEPTQFPURM-UHFFFAOYSA-N 0.000 description 2
- PLVPHPBUUXBLRX-UHFFFAOYSA-N 2-methoxyiminopentan-3-one Chemical compound CCC(=O)C(C)=NOC PLVPHPBUUXBLRX-UHFFFAOYSA-N 0.000 description 2
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 2
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
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- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
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- 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
- 239000010903 husk Substances 0.000 description 1
- 238000006698 hydrazinolysis reaction Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000005470 impregnation Methods 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
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 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
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- VXOXFIZOHUKABN-UHFFFAOYSA-L magnesium N-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound C(CNC([S-])=S)NC([S-])=S.[Mg+2] VXOXFIZOHUKABN-UHFFFAOYSA-L 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 235000012245 magnesium oxide Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- ZWJNEYVWPYIKMB-UHFFFAOYSA-N methfuroxam Chemical compound CC1=C(C)OC(C)=C1C(=O)NC1=CC=CC=C1 ZWJNEYVWPYIKMB-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 description 1
- 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 description 1
- LVCDXCQFSONNDO-UHFFFAOYSA-N n-benzylhydroxylamine Chemical compound ONCC1=CC=CC=C1 LVCDXCQFSONNDO-UHFFFAOYSA-N 0.000 description 1
- OYRIKLVYHTWHCZ-UHFFFAOYSA-N n-cyclohexyl-2,5-dimethylfuran-3-carboxamide Chemical compound O1C(C)=CC(C(=O)NC2CCCCC2)=C1C OYRIKLVYHTWHCZ-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 230000009935 nitrosation Effects 0.000 description 1
- 238000007034 nitrosation reaction Methods 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 238000006146 oximation reaction Methods 0.000 description 1
- 125000003544 oxime group Chemical group 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 150000007965 phenolic acids Chemical class 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 1
- KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical compound O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 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
- 238000007127 saponification reaction Methods 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 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
- A01N37/50—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 the nitrogen atom being doubly bound to the carbon skeleton
-
- 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
- A01N37/36—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 singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
- C07C251/60—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by carboxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19539324A DE19539324A1 (de) | 1995-10-23 | 1995-10-23 | Phenylessigsäurederivate, Verfahren und Zwischenprodukte zu ihrer Herstellung und sie enthaltende Mittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ124398A3 CZ124398A3 (cs) | 1998-09-16 |
| CZ293561B6 true CZ293561B6 (cs) | 2004-06-16 |
Family
ID=7775490
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ19981243A CZ293561B6 (cs) | 1995-10-23 | 1996-10-11 | Derivát kyseliny fenyloctové, způsob přípravy těchto sloučenin, meziprodukt, prostředek s jeho obsahem a způsob potlačování živočišných škůdců nebo škodlivých hub |
Country Status (25)
| Country | Link |
|---|---|
| US (2) | US5948932A (enExample) |
| EP (1) | EP0876332B1 (enExample) |
| JP (1) | JP4060359B2 (enExample) |
| KR (1) | KR100480395B1 (enExample) |
| CN (1) | CN1131851C (enExample) |
| AR (1) | AR004087A1 (enExample) |
| AT (1) | ATE202553T1 (enExample) |
| AU (1) | AU713475B2 (enExample) |
| BR (1) | BR9611269A (enExample) |
| CA (1) | CA2232374C (enExample) |
| CZ (1) | CZ293561B6 (enExample) |
| DE (2) | DE19539324A1 (enExample) |
| DK (1) | DK0876332T3 (enExample) |
| EA (1) | EA000786B1 (enExample) |
| ES (1) | ES2160257T3 (enExample) |
| GR (1) | GR3036214T3 (enExample) |
| HU (1) | HU225984B1 (enExample) |
| IL (3) | IL137394A (enExample) |
| NZ (1) | NZ320214A (enExample) |
| PL (1) | PL185248B1 (enExample) |
| PT (1) | PT876332E (enExample) |
| TW (1) | TW349940B (enExample) |
| UA (1) | UA48991C2 (enExample) |
| WO (1) | WO1997015552A1 (enExample) |
| ZA (1) | ZA968850B (enExample) |
Families Citing this family (75)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19724200A1 (de) | 1997-06-09 | 1998-12-10 | Basf Ag | Bisiminosubstituierte Phenylverbindungen |
| EP0934935A1 (de) | 1998-02-05 | 1999-08-11 | Basf Aktiengesellschaft | Heterocyclylsubstituierte Phenylverbindungen, Verfahren und Zwischenprodukte zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Schadpilzen und tierischen Schädlingen |
| CN1144523C (zh) * | 1998-03-24 | 2004-04-07 | 巴斯福股份公司 | 基于三(肟醚)衍生物和抗性诱导剂的杀真菌混合物 |
| IL138296A0 (en) * | 1998-03-24 | 2001-10-31 | Basf Ag | Fungicide mixtures based on triple oxime ether derivatives and rice fungicides |
| CA2323661A1 (en) * | 1998-03-24 | 1999-09-30 | Basf Aktiengesellschaft | Fungicide mixtures based on triple oxime ether derivatives and rhizoctonia fungicides |
| JP4458666B2 (ja) * | 1998-03-24 | 2010-04-28 | ビーエーエスエフ ソシエタス・ヨーロピア | トリス（オキシムエーテル）誘導体及び殺虫剤を基礎とする殺菌剤混合物 |
| ID26490A (id) * | 1998-03-24 | 2001-01-11 | Basf Ag | Campuran fungisidal berdasar turunan-turunan tris (oksimeter) dan juga fungisida-fungisida |
| CN1149924C (zh) * | 1998-03-24 | 2004-05-19 | 巴斯福股份公司 | 基于三(肟醚)衍生物和其它嗜球果伞素的杀真菌混合物 |
| EP0974578A3 (de) | 1998-07-21 | 2003-04-02 | Basf Aktiengesellschaft | Phenylcarbamate, Verfahren und Zwischenprodukte zu ihrer Herstellung und sie enthaltende pestizide und fungizide Mittel |
| ATE254846T1 (de) * | 1998-08-05 | 2003-12-15 | Basf Ag | Bodengranulate mit kontrollierter wirkstofffreisetzung (cr-bodengranulate) |
| WO2000018726A1 (de) * | 1998-09-30 | 2000-04-06 | Basf Aktiengesellschaft | Verfahren zur herstellung von trion-bis(oximether) derivaten sowie damit erhältliche trion-mono- und trion-bis(oximether) derivate |
| US6537989B1 (en) | 1998-10-15 | 2003-03-25 | Basf Aktiengesellschaft | Azadioxacycloalkene derivatives, methods for the production thereof and their use as fungicides and pest control agents |
| ATE268747T1 (de) | 1999-12-07 | 2004-06-15 | Basf Ag | Verfahren zur herstellung von o- chlormethylbenzoesäurechloriden |
| DE10019758A1 (de) * | 2000-04-20 | 2001-10-25 | Bayer Ag | Fungizide Wirkstoffkombinationen |
| HUP0301141A3 (en) * | 2000-07-05 | 2005-01-28 | Basf Ag | Method for the production of trioxime derivatives |
| WO2002047481A2 (en) * | 2000-11-17 | 2002-06-20 | The Ohio State University Research Foundation | Direct application of desiccated entomopathogenic nematodes for biological pest control |
| TWI277391B (en) * | 2000-12-18 | 2007-04-01 | Basf Ag | Fungicidal mixtures based on oxime ether derivatives |
| US20040029944A1 (en) * | 2001-01-16 | 2004-02-12 | Thomas Grote | Fungicide mixtures |
| JP2004521886A (ja) * | 2001-01-18 | 2004-07-22 | ビーエーエスエフ アクチェンゲゼルシャフト | 殺菌性混合物 |
| DE10141618A1 (de) * | 2001-08-24 | 2003-03-06 | Bayer Cropscience Ag | Fungizide Wirkstoffkombinationen |
| KR100955966B1 (ko) * | 2002-01-17 | 2010-05-04 | 바스프 에스이 | 옥심 에테르 유도체 및 구아니딘 유도체를 기재로 한살진균성 혼합물 |
| NZ534781A (en) * | 2002-03-01 | 2007-09-28 | Basf Ag | Fungicidal mixtures based on prothioconazole and trifloxystrobin |
| IL164049A0 (en) * | 2002-04-05 | 2005-12-18 | Basf Ag | Fungicidal mixtures based on benzamidoxime derivatives and a strobilur in derivative |
| WO2003084331A1 (de) * | 2002-04-10 | 2003-10-16 | Basf Aktiengesellschaft | Verfahren zur erhöhung der widerstandskraft von pflanzen gegen die phytotoxizität von agrochemikalien |
| JP4414340B2 (ja) | 2002-11-12 | 2010-02-10 | ビーエーエスエフ ソシエタス・ヨーロピア | グリホサート耐性マメ科植物の収穫量を改善する方法 |
| AU2003292024A1 (en) * | 2002-11-15 | 2004-06-15 | Basf Aktiengesellschaft | Fungicidal mixtures for controlling rice pathogens |
| DE10333373A1 (de) | 2003-07-23 | 2005-02-10 | Bayer Ag | Fungizide Wirkstoffkombinationen |
| DE10347090A1 (de) | 2003-10-10 | 2005-05-04 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| DE10349501A1 (de) | 2003-10-23 | 2005-05-25 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| UA85690C2 (ru) | 2003-11-07 | 2009-02-25 | Басф Акциенгезелльшафт | Смесь для применения в сельском хозяйстве, содержащая стробилурин и модулятор этилена, способ обработки и борьбы с инфекциями в бобовых культурах |
| EP2255628A3 (de) | 2004-04-30 | 2012-09-19 | Basf Se | Fungizide Mischungen |
| DE502005003114D1 (de) * | 2004-06-17 | 2008-04-17 | Basf Se | Verwendung von (e)-5-(4-chlorbenzyliden)-2,2-dimethyl-1-(1h-1,2,4-triazol-1-ylmethyl)cyclopentanol zur bekämpfung des rostbefalls an sojapflanzen |
| DE102004062513A1 (de) | 2004-12-24 | 2006-07-06 | Bayer Cropscience Ag | Insektizide auf Basis von Neonicotinoiden und ausgewählten Strobilurinen |
| DE102005015677A1 (de) | 2005-04-06 | 2006-10-12 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| WO2006131230A2 (de) | 2005-06-09 | 2006-12-14 | Bayer Cropscience Ag | Wirkstoffkombinationen |
| DE102005026482A1 (de) | 2005-06-09 | 2006-12-14 | Bayer Cropscience Ag | Wirkstoffkombinationen |
| DE102005035300A1 (de) * | 2005-07-28 | 2007-02-01 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100187541B1 (ko) * | 1988-12-29 | 1999-06-01 | 쟝-자크 오가이; 롤란트 보러 | 알디미노-또는 케티미노-옥시-오르토-톨릴아크릴산의 메틸 에스테르,이의 제조방법 및 이를 함유하는 살진균제 |
| IL105191A (en) * | 1992-04-04 | 1998-08-16 | Basf Ag | Acids and aminooxymethylbenzoic acids and their preparation |
| HU219157B (hu) * | 1994-01-05 | 2001-02-28 | Novartis Ag. | Peszticid hatású [dioxa-diaza/vagy oxa-triaza/-heptadienil-fenil]-akrilsav- és glioxilsav-származékok, előállításuk és alkalmazásuk |
| ES2150550T3 (es) * | 1994-02-04 | 2000-12-01 | Basf Ag | Derivados de acido fenilacetico, procedimientos y productos intermedios para su obtencion, y agentes que los contienen. |
| DE59510619D1 (de) * | 1994-02-04 | 2003-05-08 | Basf Ag | Phenylessigsäurederivate, verfahren und zwischenprodukte zu ihrer herstellung und sie enthaltende mittel |
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1995
- 1995-10-23 DE DE19539324A patent/DE19539324A1/de not_active Withdrawn
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- 1996-10-11 DK DK96934659T patent/DK0876332T3/da active
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- 1996-10-11 KR KR10-1998-0702912A patent/KR100480395B1/ko not_active Expired - Fee Related
- 1996-10-11 DE DE59607186T patent/DE59607186D1/de not_active Expired - Lifetime
- 1996-10-11 HU HU9802578A patent/HU225984B1/hu not_active IP Right Cessation
- 1996-10-11 CZ CZ19981243A patent/CZ293561B6/cs not_active IP Right Cessation
- 1996-10-11 PT PT96934659T patent/PT876332E/pt unknown
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- 1996-10-17 TW TW085112679A patent/TW349940B/zh not_active IP Right Cessation
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| Date | Code | Title | Description |
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| PD00 | Pending as of 2000-06-30 in czech republic | ||
| MM4A | Patent lapsed due to non-payment of fee |
Effective date: 20131011 |