NZ320214A - Phenylacetic acid derivatives and hydroxyimino intermediates for use in producing them and agents containing them - Google Patents

Phenylacetic acid derivatives and hydroxyimino intermediates for use in producing them and agents containing them

Info

Publication number: NZ320214A
Authority: NZ; New Zealand
Prior art keywords: compounds; methyl; substituent; general formula; line
Prior art date: 1995-10-23

Application number

NZ320214A

Other languages

English (en)

Inventor

Thomas Grote

Herbert Bayer

Ruth Muller

Hubert Sauter

Reinhard Kirstgen

Volker Harries

Gisela Lorenz

Eberhard Ammermann

Siegfried Strathmann

Original Assignee

Basf Ag

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

1999-04-29

1996-10-11 Application filed by Basf Ag filed Critical Basf Ag

1999-04-29 Publication of NZ320214A publication Critical patent/NZ320214A/en

Links

-1 hydroxyimino Chemical group 0.000 title claims description 255
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 title claims description 7
239000000543 intermediate Substances 0.000 title description 5
239000003795 chemical substances by application Substances 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 3054
125000001424 substituent group Chemical group 0.000 claims description 994
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 981
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 333
239000004480 active ingredient Substances 0.000 claims description 38
239000000203 mixture Substances 0.000 claims description 38
125000004093 cyano group Chemical group *C#N 0.000 claims description 30
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 29
125000001072 heteroaryl group Chemical group 0.000 claims description 29
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 22
239000001257 hydrogen Substances 0.000 claims description 21
229910052739 hydrogen Inorganic materials 0.000 claims description 21
238000000034 method Methods 0.000 claims description 21
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
125000003118 aryl group Chemical group 0.000 claims description 19
229910052757 nitrogen Inorganic materials 0.000 claims description 18
229910052736 halogen Inorganic materials 0.000 claims description 16
150000002367 halogens Chemical group 0.000 claims description 16
229910052717 sulfur Inorganic materials 0.000 claims description 16
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
238000002360 preparation method Methods 0.000 claims description 14
241000233866 Fungi Species 0.000 claims description 13
125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 claims description 13
125000004104 aryloxy group Chemical group 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
241000607479 Yersinia pestis Species 0.000 claims description 11
229910052760 oxygen Inorganic materials 0.000 claims description 11
239000001301 oxygen Substances 0.000 claims description 11
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 10
230000015572 biosynthetic process Effects 0.000 claims description 10
238000003786 synthesis reaction Methods 0.000 claims description 10
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 9
241001465754 Metazoa Species 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 9
125000005110 aryl thio group Chemical group 0.000 claims description 9
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
239000000463 material Substances 0.000 claims description 9
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
125000000623 heterocyclic group Chemical group 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 7
239000011593 sulfur Substances 0.000 claims description 7
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000005844 heterocyclyloxy group Chemical group 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
125000003302 alkenyloxy group Chemical group 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
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
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 claims description 5
UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 claims description 4
101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000003282 alkyl amino group Chemical group 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 4
125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
125000001188 haloalkyl group Chemical group 0.000 claims description 4
241000239223 Arachnida Species 0.000 claims description 3
239000004215 Carbon black (E152) Substances 0.000 claims description 3
241000238631 Hexapoda Species 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
125000004670 alkyl amino thio carbonyl group Chemical group 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
125000004122 cyclic group Chemical group 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
229930195733 hydrocarbon Natural products 0.000 claims description 3
125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 2
241001330975 Magnaporthe oryzae Species 0.000 claims description 2
239000000654 additive Substances 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
125000005087 alkynylcarbonyl group Chemical group 0.000 claims description 2
125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
125000004438 haloalkoxy group Chemical group 0.000 claims description 2
125000003107 substituted aryl group Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
125000000000 cycloalkoxy group Chemical group 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
230000001681 protective effect Effects 0.000 claims 1
125000003396 thiol group Chemical class [H]S* 0.000 claims 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 327
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 28
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
125000004433 nitrogen atom Chemical group N* 0.000 description 22
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 17
125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 17
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 15
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 14
239000003921 oil Substances 0.000 description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 14
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
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
125000001541 3-thienyl group Chemical group S1C([H])=C([*])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
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
125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 description 12
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 12
125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 description 12
125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 description 11
125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 description 11
241000196324 Embryophyta Species 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
125000004510 1,3,4-oxadiazol-5-yl group Chemical group O1C=NN=C1* 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
125000004432 carbon atom Chemical group C* 0.000 description 9
125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 description 9
125000004434 sulfur atom Chemical group 0.000 description 9
239000000417 fungicide Substances 0.000 description 8
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
240000006365 Vitis vinifera Species 0.000 description 7
235000014787 Vitis vinifera Nutrition 0.000 description 7
230000000694 effects Effects 0.000 description 7
239000003995 emulsifying agent Substances 0.000 description 7
238000009472 formulation Methods 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
102100035861 Cytosolic 5'-nucleotidase 1A Human genes 0.000 description 6
101000802744 Homo sapiens Cytosolic 5'-nucleotidase 1A Proteins 0.000 description 6
101100054666 Streptomyces halstedii sch3 gene Proteins 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
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
239000006185 dispersion Substances 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
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
239000000969 carrier Substances 0.000 description 5
235000013339 cereals Nutrition 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000000839 emulsion Substances 0.000 description 5
239000008187 granular material Substances 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
239000006072 paste Substances 0.000 description 5
OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical compound [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 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
239000007921 spray Substances 0.000 description 5
235000013311 vegetables Nutrition 0.000 description 5
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 4
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
239000004359 castor oil Substances 0.000 description 4
235000019438 castor oil Nutrition 0.000 description 4
125000000753 cycloalkyl group Chemical group 0.000 description 4
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 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
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 4
235000012054 meals Nutrition 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-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
239000007787 solid Substances 0.000 description 4
241000894007 species Species 0.000 description 4
238000005507 spraying Methods 0.000 description 4
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 4
239000002699 waste material Substances 0.000 description 4
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 3
SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 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
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
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
101150041968 CDC13 gene Proteins 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
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
240000007594 Oryza sativa Species 0.000 description 3
235000007164 Oryza sativa Nutrition 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
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 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
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
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 3
239000011707 mineral Substances 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
MVDYEFQVZNBPPH-UHFFFAOYSA-N pentane-2,3,4-trione Chemical compound CC(=O)C(=O)C(C)=O MVDYEFQVZNBPPH-UHFFFAOYSA-N 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
235000009566 rice Nutrition 0.000 description 3
239000000126 substance Substances 0.000 description 3
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
239000000725 suspension Substances 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
125000006017 1-propenyl group Chemical group 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 2
125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
239000005995 Aluminium silicate Substances 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
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
JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 description 2
108010081348 HRT1 protein Hairy Proteins 0.000 description 2
102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 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
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
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150000002170 ethers Chemical class 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
JFSPBVWPKOEZCB-UHFFFAOYSA-N fenfuram Chemical compound O1C=CC(C(=O)NC=2C=CC=CC=2)=C1C JFSPBVWPKOEZCB-UHFFFAOYSA-N 0.000 description 1
239000000835 fiber Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 description 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
UYJUZNLFJAWNEZ-UHFFFAOYSA-N fuberidazole Chemical compound C1=COC(C=2NC3=CC=CC=C3N=2)=C1 UYJUZNLFJAWNEZ-UHFFFAOYSA-N 0.000 description 1
230000002538 fungal effect Effects 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
238000000227 grinding Methods 0.000 description 1
239000003630 growth substance Substances 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
CKAPSXZOOQJIBF-UHFFFAOYSA-N hexachlorobenzene Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CKAPSXZOOQJIBF-UHFFFAOYSA-N 0.000 description 1
238000006698 hydrazinolysis reaction Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 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
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
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
125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([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
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 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
ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-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
125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 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
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
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
239000000575 pesticide Substances 0.000 description 1
239000012071 phase Substances 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
125000005328 phosphinyl group Chemical group [PH2](=O)* 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
KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical compound O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 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
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
229960005335 propanol Drugs 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
125000000714 pyrimidinyl group Chemical group 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
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
150000003467 sulfuric acid derivatives Chemical class 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
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
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
KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical class CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-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
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)

NZ320214A 1995-10-23 1996-10-11 Phenylacetic acid derivatives and hydroxyimino intermediates for use in producing them and agents containing them NZ320214A (en)

Applications Claiming Priority (2)

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
PCT/EP1996/004446 WO1997015552A1 (de)	1995-10-23	1996-10-11	Phenylessigsäurederivate, verfahren und zwischenprodukte zu ihrer herstellung und sie enthaltende mittel

Publications (1)

Publication Number	Publication Date
NZ320214A true NZ320214A (en)	1999-04-29

Family

ID=7775490

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NZ320214A NZ320214A (en)	1995-10-23	1996-10-11	Phenylacetic acid derivatives and hydroxyimino intermediates for use in producing them and agents containing 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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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
EP1065927A1 (de) *	1998-03-24	2001-01-10	Basf Aktiengesellschaft	Fungizide mischungen auf der basis von tripeloximetherderivaten und rhizoctonia-fungiziden
IL138296A0 (en) *	1998-03-24	2001-10-31	Basf Ag	Fungicide mixtures based on triple oxime ether derivatives and rice fungicides
KR100557363B1 (ko) *	1998-03-24	2006-03-10	바스프 악티엔게젤샤프트	삼옥심에테르 유도체 및 다른 스트로빌루린을 기본으로하는 살진균제 혼합물
IL138166A0 (en) *	1998-03-24	2001-10-31	Basf Ag	Fungicide mixtures based on triple oxime ether derivatives and additional fungicides
JP4458668B2 (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）誘導体及び抗誘導物質を基礎とする殺菌剤混合物
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
EP0974578A3 (de) *	1998-07-21	2003-04-02	Basf Aktiengesellschaft	Phenylcarbamate, Verfahren und Zwischenprodukte zu ihrer Herstellung und sie enthaltende pestizide und fungizide Mittel
ES2212601T3 (es) *	1998-08-05	2004-07-16	Basf Aktiengesellschaft	Granulador de suelo con liberacion de producto activo controlada (granulados de suelo cr.).
ATE229500T1 (de) *	1998-09-30	2002-12-15	Basf Ag	Verfahren zur herstellung von trion- bis(oximether) derivaten sowie damit erhältliche trion-mono- und trion-bis(oximether) derivate
ATE261433T1 (de)	1998-10-15	2004-03-15	Basf Ag	Azadioxacycloalkene derivate, verfahren zu deren herstellung sowie deren verwendung als fungizide und schädlingsbekämpfungsmittel
PL357592A1 (en)	1999-12-07	2004-07-26	Basf Aktiengesellschaft	Method for producing o-chloromethyl benzoic acid chlorides
DE10019758A1 (de)	2000-04-20	2001-10-25	Bayer Ag	Fungizide Wirkstoffkombinationen
EP1296939B1 (de) *	2000-07-05	2005-11-09	Basf Aktiengesellschaft	Verfahren zur herstellung von trioximderivaten
WO2002047481A2 (en) *	2000-11-17	2002-06-20	The Ohio State University Research Foundation	Direct application of desiccated entomopathogenic nematodes for biological pest control
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
DE10141618A1 (de) *	2001-08-24	2003-03-06	Bayer Cropscience Ag	Fungizide Wirkstoffkombinationen
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
WO2003084331A1 (de) *	2002-04-10	2003-10-16	Basf Aktiengesellschaft	Verfahren zur erhöhung der widerstandskraft von pflanzen gegen die phytotoxizität von agrochemikalien
BR0316180B1 (pt)	2002-11-12	2014-10-21	Basf Ag	Processo para aumentar o rendimento em legumes resistentes ao glifosato, e, mistura
CA2505498A1 (en) *	2002-11-15	2004-06-03	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
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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
- 1996-10-11 CA CA002232374A patent/CA2232374C/en not_active Expired - Fee Related
- 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
- 1996-10-11 IL IL13739496A patent/IL137394A/xx not_active IP Right Cessation
- 1996-10-11 JP JP51624697A patent/JP4060359B2/ja not_active Expired - Fee Related
- 1996-10-11 PL PL96326509A patent/PL185248B1/pl not_active IP Right Cessation
- 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 BR BR9611269A patent/BR9611269A/pt not_active IP Right Cessation
- 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
- 1996-10-23 AR ARP960104877A patent/AR004087A1/es active IP Right Grant
1999
- 1999-01-14 US US09/229,972 patent/US6037378A/en not_active Expired - Lifetime
2000
- 2000-07-19 IL IL13739400A patent/IL137394A0/xx unknown
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
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
AU713475B2 (en)	1999-12-02
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

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