AU713475B2 - Phenylacetic acid derivatives, processes and intermediates for their preparation, and compositions comprising them - Google Patents

Phenylacetic acid derivatives, processes and intermediates for their preparation, and compositions comprising them Download PDF

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Publication number: AU713475B2
Authority: AU; Australia
Prior art keywords: compounds; methyl; substituent; general formula; line
Prior art date: 1995-10-23
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Ceased

Application number

AU72915/96A

Other languages

English (en)

Other versions

AU7291596A (en

Inventor

Eberhard Ammermann

Herbert Bayer

Thomas Grote

Volker Harries

Reinhard Kirstgen

Gisela Lorenz

Ruth Muller

Hubert Sauter

Siegfried Strathmann

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF SE

Original Assignee

BASF SE

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1995-10-23

Filing date

1996-10-11

Publication date

1999-12-02

1996-10-11 Application filed by BASF SE filed Critical BASF SE

1997-05-15 Publication of AU7291596A publication Critical patent/AU7291596A/en

1999-12-02 Application granted granted Critical

1999-12-02 Publication of AU713475B2 publication Critical patent/AU713475B2/en

2016-10-11 Anticipated expiration legal-status Critical

Status Ceased legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title description 34
238000000034 method Methods 0.000 title description 17
238000002360 preparation method Methods 0.000 title description 12
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 title description 6
239000000543 intermediate Substances 0.000 title description 4
150000001875 compounds Chemical class 0.000 description 3058
125000001424 substituent group Chemical group 0.000 description 997
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 975
-1 nitro, hydroxyl Chemical group 0.000 description 252
239000004480 active ingredient Substances 0.000 description 38
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 29
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 25
101150065749 Churc1 gene Proteins 0.000 description 25
102100038239 Protein Churchill Human genes 0.000 description 25
125000001072 heteroaryl group Chemical group 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
125000004093 cyano group Chemical group *C#N 0.000 description 23
125000004433 nitrogen atom Chemical group N* 0.000 description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000000460 chlorine Substances 0.000 description 15
239000000243 solution Substances 0.000 description 15
229910052717 sulfur Inorganic materials 0.000 description 15
125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
239000003921 oil Substances 0.000 description 14
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 description 13
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 13
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 13
229910052757 nitrogen Inorganic materials 0.000 description 13
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 13
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 12
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 12
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 12
229910052739 hydrogen Inorganic materials 0.000 description 12
125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 description 12
125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 description 12
125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 description 12
125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 description 12
125000004510 1,3,4-oxadiazol-5-yl group Chemical group O1C=NN=C1* 0.000 description 11
241000196324 Embryophyta Species 0.000 description 11
238000005481 NMR spectroscopy Methods 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
229910052736 halogen Inorganic materials 0.000 description 11
150000002367 halogens Chemical group 0.000 description 11
239000001257 hydrogen Substances 0.000 description 11
125000003118 aryl group Chemical group 0.000 description 10
125000000882 C2-C6 alkenyl group Chemical group 0.000 description 9
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
230000015572 biosynthetic process Effects 0.000 description 9
125000004432 carbon atom Chemical group C* 0.000 description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
229910052760 oxygen Inorganic materials 0.000 description 9
239000001301 oxygen Substances 0.000 description 9
125000004434 sulfur atom Chemical group 0.000 description 9
238000003786 synthesis reaction Methods 0.000 description 9
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
241000233866 Fungi Species 0.000 description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
230000000694 effects Effects 0.000 description 8
239000003995 emulsifying agent Substances 0.000 description 8
239000000417 fungicide Substances 0.000 description 8
239000000463 material Substances 0.000 description 8
101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
240000006365 Vitis vinifera Species 0.000 description 7
235000014787 Vitis vinifera Nutrition 0.000 description 7
125000004104 aryloxy group Chemical group 0.000 description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
238000009472 formulation Methods 0.000 description 7
150000003839 salts Chemical class 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
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
241000607479 Yersinia pestis Species 0.000 description 6
125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 description 6
125000005110 aryl thio group Chemical group 0.000 description 6
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 6
239000006185 dispersion Substances 0.000 description 6
239000000839 emulsion Substances 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
125000004430 oxygen atom Chemical group O* 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
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
239000011593 sulfur Substances 0.000 description 6
125000003320 C2-C6 alkenyloxy group Chemical group 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 5
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
239000000969 carrier Substances 0.000 description 5
235000013339 cereals Nutrition 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000008187 granular material Substances 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
150000003254 radicals Chemical class 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
239000002904 solvent Substances 0.000 description 5
235000013311 vegetables Nutrition 0.000 description 5
125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 4
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
125000003601 C2-C6 alkynyl group Chemical group 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
240000007594 Oryza sativa Species 0.000 description 4
235000007164 Oryza sativa Nutrition 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
239000004359 castor oil Substances 0.000 description 4
235000019438 castor oil Nutrition 0.000 description 4
239000002270 dispersing agent Substances 0.000 description 4
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 4
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
235000012054 meals Nutrition 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
235000009566 rice Nutrition 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000007921 spray Substances 0.000 description 4
238000005507 spraying Methods 0.000 description 4
239000000725 suspension Substances 0.000 description 4
239000002699 waste material Substances 0.000 description 4
238000005160 1H NMR spectroscopy Methods 0.000 description 3
NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical class CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical class COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-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
241000221785 Erysiphales Species 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
241001330975 Magnaporthe oryzae Species 0.000 description 3
241000244206 Nematoda Species 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
241001281803 Plasmopara viticola Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
235000012211 aluminium silicate Nutrition 0.000 description 3
125000003710 aryl alkyl group Chemical group 0.000 description 3
125000005160 aryl oxy alkyl group Chemical group 0.000 description 3
239000002585 base Substances 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
229910052801 chlorine Inorganic materials 0.000 description 3
125000000623 heterocyclic group Chemical group 0.000 description 3
125000005844 heterocyclyloxy group Chemical group 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
239000011707 mineral Substances 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
229920000151 polyglycol Polymers 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
241000894007 species Species 0.000 description 3
239000000126 substance Substances 0.000 description 3
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
239000008096 xylene Substances 0.000 description 3
ZVJBPHMCBRHVEV-GQCTYLIASA-N (2e)-2-hydroxyiminopentan-3-one Chemical compound CCC(=O)C(\C)=N\O ZVJBPHMCBRHVEV-GQCTYLIASA-N 0.000 description 2
125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 2
SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 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
239000005995 Aluminium silicate Substances 0.000 description 2
241000239223 Arachnida Species 0.000 description 2
241001480061 Blumeria graminis Species 0.000 description 2
JQJPBYFTQAANLE-UHFFFAOYSA-N Butyl nitrite Chemical compound CCCCON=O JQJPBYFTQAANLE-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241000191839 Chrysomya Species 0.000 description 2
241000254173 Coleoptera Species 0.000 description 2
229920000742 Cotton Polymers 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
241000238631 Hexapoda Species 0.000 description 2
240000005979 Hordeum vulgare Species 0.000 description 2
235000007340 Hordeum vulgare Nutrition 0.000 description 2
241000257303 Hymenoptera Species 0.000 description 2
241000694408 Isomeris Species 0.000 description 2
241000256602 Isoptera Species 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
244000070406 Malus silvestris Species 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
240000000111 Saccharum officinarum Species 0.000 description 2
235000007201 Saccharum officinarum Nutrition 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
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
241001454293 Tetranychus urticae Species 0.000 description 2
241001414989 Thysanoptera Species 0.000 description 2
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000000853 adhesive Substances 0.000 description 2
230000001070 adhesive effect Effects 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 2
150000008052 alkyl sulfonates Chemical class 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
235000021016 apples Nutrition 0.000 description 2
125000005129 aryl carbonyl group Chemical group 0.000 description 2
125000004391 aryl sulfonyl group Chemical group 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
HJMZMZRCABDKKV-UHFFFAOYSA-N carbonocyanidic acid Chemical class OC(=O)C#N HJMZMZRCABDKKV-UHFFFAOYSA-N 0.000 description 2
150000001728 carbonyl compounds Chemical class 0.000 description 2
238000006555 catalytic reaction Methods 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 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 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
239000012990 dithiocarbamate Substances 0.000 description 2
235000013399 edible fruits Nutrition 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
150000002191 fatty alcohols Chemical class 0.000 description 2
239000003337 fertilizer Substances 0.000 description 2
230000000855 fungicidal effect Effects 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
239000004009 herbicide Substances 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
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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
208000015181 infectious disease Diseases 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
150000002500 ions Chemical class 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
239000004571 lime Substances 0.000 description 1
239000006028 limestone Substances 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
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
YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 1
WJZHMLNIAZSFDO-UHFFFAOYSA-N manganese zinc Chemical compound [Mn].[Zn] WJZHMLNIAZSFDO-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
125000002911 monocyclic heterocycle 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
125000001624 naphthyl group Chemical group 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
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 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
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
COWNFYYYZFRNOY-UHFFFAOYSA-N oxazolidinedione Chemical compound O=C1COC(=O)N1 COWNFYYYZFRNOY-UHFFFAOYSA-N 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
238000006146 oximation reaction Methods 0.000 description 1
125000000466 oxiranyl 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
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
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
229940044654 phenolsulfonic acid Drugs 0.000 description 1
229940049953 phenylacetate Drugs 0.000 description 1
230000003032 phytopathogenic effect Effects 0.000 description 1
125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
125000004585 polycyclic heterocycle group Chemical group 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical group [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 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
OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical compound [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 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
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
125000000168 pyrrolyl 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
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 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
229910052708 sodium Inorganic materials 0.000 description 1
PYODKQIVQIVELM-UHFFFAOYSA-M sodium;2,3-bis(2-methylpropyl)naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 PYODKQIVQIVELM-UHFFFAOYSA-M 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
235000021012 strawberries Nutrition 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
229920002994 synthetic fiber Polymers 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
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 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
WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-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
125000004306 triazinyl group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
238000009827 uniform distribution Methods 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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)
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)
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)

AU72915/96A 1995-10-23 1996-10-11 Phenylacetic acid derivatives, processes and intermediates for their preparation, and compositions comprising them Ceased AU713475B2 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE19539324		1995-10-23
DE19539324A DE19539324A1 (de)	1995-10-23	1995-10-23	Phenylessigsäurederivate, Verfahren und Zwischenprodukte zu ihrer Herstellung und sie enthaltende Mittel
PCT/EP1996/004446 WO1997015552A1 (de)	1995-10-23	1996-10-11	Phenylessigsäurederivate, verfahren und zwischenprodukte zu ihrer herstellung und sie enthaltende mittel

Publications (2)

Publication Number	Publication Date
AU7291596A AU7291596A (en)	1997-05-15
AU713475B2 true AU713475B2 (en)	1999-12-02

Family

ID=7775490

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AU72915/96A Ceased AU713475B2 (en)	1995-10-23	1996-10-11	Phenylacetic acid derivatives, processes and intermediates for their preparation, and compositions comprising them

Country Status (25)

Country	Link
US (2)	US5948932A (2)
EP (1)	EP0876332B1 (2)
JP (1)	JP4060359B2 (2)
KR (1)	KR100480395B1 (2)
CN (1)	CN1131851C (2)
AR (1)	AR004087A1 (2)
AT (1)	ATE202553T1 (2)
AU (1)	AU713475B2 (2)
BR (1)	BR9611269A (2)
CA (1)	CA2232374C (2)
CZ (1)	CZ293561B6 (2)
DE (2)	DE19539324A1 (2)
DK (1)	DK0876332T3 (2)
EA (1)	EA000786B1 (2)
ES (1)	ES2160257T3 (2)
GR (1)	GR3036214T3 (2)
HU (1)	HU225984B1 (2)
IL (3)	IL137394A (2)
NZ (1)	NZ320214A (2)
PL (1)	PL185248B1 (2)
PT (1)	PT876332E (2)
TW (1)	TW349940B (2)
UA (1)	UA48991C2 (2)
WO (1)	WO1997015552A1 (2)
ZA (1)	ZA968850B (2)

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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
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AU2002235781A1 (en) *	2000-12-18	2002-07-01	Basf Aktiengesellschaft	Fungicide mixtures based on oxime ether derivatives
BR0206451A (pt) *	2001-01-16	2003-12-30	Basf Ag	Mistura fungicida, método para combater fungos nocivos, e, agente fungicida
US20040054011A1 (en) *	2001-01-18	2004-03-18	Thomas Grote	Fungicidal mixtures
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WO2003059067A1 (de) *	2002-01-17	2003-07-24	Basf Aktiengesellschaft	Fungizide mischungen auf der basis von oximetherderivaten_und guanidinderivaten
NZ555498A (en) *	2002-03-01	2008-07-31	Basf Ag	Fungicidal mixtures based on prothioconazole and a picoxystrobin
WO2003084329A1 (de) *	2002-04-05	2003-10-16	Basf Aktiengesellschaft	Fungizide mischungen auf der basis von benzamidoxim-derivaten und einem strobilurin-derivat
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CA2560341A1 (en)	2004-04-30	2005-11-10	Jordi Tormo I Blasco	Fungicidal mixtures
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1995
- 1995-10-23 DE DE19539324A patent/DE19539324A1/de not_active Withdrawn
1996
- 1996-10-11 EA EA199800388A patent/EA000786B1/ru not_active IP Right Cessation
- 1996-10-11 HU HU9802578A patent/HU225984B1/hu not_active IP Right Cessation
- 1996-10-11 CN CN96197824A patent/CN1131851C/zh not_active Expired - Fee Related
- 1996-10-11 EP EP96934659A patent/EP0876332B1/de not_active Expired - Lifetime
- 1996-10-11 CZ CZ19981243A patent/CZ293561B6/cs not_active IP Right Cessation
- 1996-10-11 ES ES96934659T patent/ES2160257T3/es not_active Expired - Lifetime
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- 1996-10-11 NZ NZ320214A patent/NZ320214A/en not_active IP Right Cessation
- 1996-10-11 DE DE59607186T patent/DE59607186D1/de not_active Expired - Lifetime
- 1996-10-11 KR KR10-1998-0702912A patent/KR100480395B1/ko not_active Expired - Fee Related
- 1996-10-11 PT PT96934659T patent/PT876332E/pt unknown
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- 1996-10-11 UA UA98052687A patent/UA48991C2/uk unknown
- 1996-10-11 AT AT96934659T patent/ATE202553T1/de active
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- 1996-10-11 WO PCT/EP1996/004446 patent/WO1997015552A1/de not_active Ceased
- 1996-10-11 AU AU72915/96A patent/AU713475B2/en not_active Ceased
- 1996-10-11 DK DK96934659T patent/DK0876332T3/da active
- 1996-10-17 TW TW085112679A patent/TW349940B/zh not_active IP Right Cessation
- 1996-10-22 ZA ZA9608850A patent/ZA968850B/xx unknown
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1999
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2000
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2001
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Also Published As

Publication number	Publication date
TW349940B (en)	1999-01-11
CA2232374A1 (en)	1997-05-01
PL185248B1 (pl)	2003-04-30
IL137394A (en)	2003-11-23
UA48991C2 (uk)	2002-09-16
EP0876332A1 (de)	1998-11-11
BR9611269A (pt)	1999-03-30
IL123861A0 (en)	1998-10-30
NZ320214A (en)	1999-04-29
DE19539324A1 (de)	1997-04-24
EA199800388A1 (ru)	1998-12-24
HUP9802578A2 (hu)	1999-02-01
AU7291596A (en)	1997-05-15
AR004087A1 (es)	1998-09-30
ZA968850B (en)	1998-04-22
HUP9802578A3 (en)	2001-12-28
HU225984B1 (en)	2008-02-28
CZ124398A3 (cs)	1998-09-16
DE59607186D1 (de)	2001-08-02
JP4060359B2 (ja)	2008-03-12
US6037378A (en)	2000-03-14
PT876332E (pt)	2001-11-30
IL123861A (en)	2003-01-12
KR100480395B1 (ko)	2005-05-16
EA000786B1 (ru)	2000-04-24
IL137394A0 (en)	2001-07-24
GR3036214T3 (en)	2001-10-31
WO1997015552A1 (de)	1997-05-01
JPH11513695A (ja)	1999-11-24
CZ293561B6 (cs)	2004-06-16
DK0876332T3 (da)	2001-09-03
EP0876332B1 (de)	2001-06-27
CA2232374C (en)	2005-08-16
CN1131851C (zh)	2003-12-24
ES2160257T3 (es)	2001-11-01
KR19990066979A (ko)	1999-08-16
ATE202553T1 (de)	2001-07-15
PL326509A1 (en)	1998-09-28
US5948932A (en)	1999-09-07
CN1200726A (zh)	1998-12-02

Legal Events

Date	Code	Title	Description
2000-03-30	FGA	Letters patent sealed or granted (standard patent)

Publication	Publication Date	Title
AU713475B2 (en)	1999-12-02	Phenylacetic acid derivatives, processes and intermediates for their preparation, and compositions comprising them
RU2165411C2 (ru)	2001-04-20	Производные фенилуксусной кислоты, промежуточные продукты для их получения и содержащие их средства
AU681932B2 (en)	1997-09-11	Phenyl acetic acid derivatives, process and intermediate products for their production and agents containing them
EP0793645B1 (de)	1999-04-28	Iminooxymethylenanilide, verfahren und zwischenprodukte zu ihrer herstellung und sie enthaltende schädlingsbekämfungsmittel
AU713472B2 (en)	1999-12-02	Phenylacetic acid derivatives, processes and intermediates for their preparation, and compositions comprising them
AU686304B2 (en)	1998-02-05	Phenylthio acetic acid derivatives, process and intermediateproducts for their production and agents containing them
US6043282A (en)	2000-03-28	Azinooximethers, processes and intermediate products for manufacturing same, and the uses thereof in combating harmful fungi and pests
US6075049A (en)	2000-06-13	Phenylcarbamates, processes and intermediate products for their preparation and their use as pesticides and fungicides
EP0873307B1 (de)	2000-05-31	Cyaniminooximether, verfahren und zwischenprodukte zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen und tierischen schädlingen
US6509379B1 (en)	2003-01-21	Phenylacetic acid derivatives, process and intermediate products for their preparation, and their use as fungicides and pesticides
US6043197A (en)	2000-03-28	Pyridylacetic acid derivatives, process and intermediate products for their preparation and their use
US6265613B1 (en)	2001-07-24	Phenylacetic acid derivatives, process for their preparation and their use as pesticides and fungicides
AU761132B2 (en)	2003-05-29	Bisoximether derivatives, methods and intermediate products for the production thereof, and their use for combating fungicidal pests and animal pests
KR100372212B1 (ko)	2005-10-25	페닐아세트산유도체,이의제조방법및이를함유하는조성물
EP0865432A1 (de)	1998-09-23	Phenylessigsäurederivate, verfahren und zwischenprodukte zu ihrer herstellung und ihre verwendung als pestizide und/oder fungizide
PT854861E (pt)	2002-01-30	Eteres de oxamino-oxima processo e produtos intermedios para a sua preparacao e agentes que os contem para o combate a fungos parasitas e parasitas animais