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 PDF

Info

Publication number: CZ293561B6
Authority: CZ; Czechia
Prior art keywords: compounds; formula; methyl; compound; row
Prior art date: 1995-10-23

Application number

CZ19981243A

Other languages

Czech (cs)

English (en)

Other versions

CZ124398A3 (cs

Inventor

Thomas Dr. Grote

Herbert Dr. Bayer

Ruth Dr. Müller

Hubert Dr. Sauter

Reinhard Dr. Kirstgen

Volker Dr. Harries

Gisela Dr. Lorenz

Eberhard Dr. Ammermann

Siegfried Dr. Strathmann

Original Assignee

Basf Aktiengesellschaft

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

2004-06-16

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

1998-09-16 Publication of CZ124398A3 publication Critical patent/CZ124398A3/cs

2004-06-16 Publication of CZ293561B6 publication Critical patent/CZ293561B6/cs

Links

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
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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
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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
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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
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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
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235000021307 Triticum Nutrition 0.000 description 6
239000002253 acid Substances 0.000 description 6
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230000000694 effects Effects 0.000 description 6
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BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
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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
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125000006163 5-membered heteroaryl group Chemical group 0.000 description 5
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235000011152 sodium sulphate Nutrition 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
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238000005481 NMR spectroscopy Methods 0.000 description 4
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ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
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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)
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)

CZ19981243A 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 CZ293561B6 (cs)

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 (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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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
- 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 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
- 1999-01-14 US US09/229,972 patent/US6037378A/en not_active Expired - Lifetime
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
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
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
2000-06-30	PD00	Pending as of 2000-06-30 in czech republic
2014-04-30	MM4A	Patent lapsed due to non-payment of fee	Effective date: 20131011

Publication	Publication Date	Title
KR100480395B1 (ko)	2005-05-16	페닐아세트산유도체,이의제조방법,이의제조에사용되는중간생성물및이를함유하는조성물
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AU5161193A (en)	1994-05-09	Pyrimidine derivative
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US20070167421A1 (en)	2007-07-19	Pyrimidine derivatives and use thereof as agricultural and horticultural fungicides
AU709902B2 (en)	1999-09-09	Iminooxyphenyl acetic acid derivatives, their preparation, intermediates for their preparation, and their use
CN1069638C (zh)	2001-08-15	唑基氧基苄基烷氧基丙烯酸酯、其制备和应用
US6075049A (en)	2000-06-13	Phenylcarbamates, processes and intermediate products for their preparation and their use as pesticides and fungicides
US6034131A (en)	2000-03-07	Diphenylethers, process and intermediate products for their preparation, and their use
US6043197A (en)	2000-03-28	Pyridylacetic acid derivatives, process and intermediate products for their preparation and their use
AU2018325894B2 (en)	2022-08-04	1-(N,N-disubstituted carbamoyl) 4-(substituted sulfonyl)triazolin-5-one derivatives, 4-(N,N-disubstituted carbamoyl) 1-(substituted sulfonyl)triazolin-5-one derivatives, and herbicide containing same as active ingredient
CA2233258A1 (en)	1997-05-09	Phenylacetic acid derivatives, their preparation, intermediates for their preparation, and their use for controlling harmful fungi and animal pests
EP0876334B1 (de)	2000-08-23	Phenylessigsäurederivate, verfahren zu ihrer herstellung und ihre verwendung als schädlingsbekämpfungsmittel und fungizide
DE19541382A1 (de)	1997-05-15	Phenylessigsäurederivate, Verfahren und Zwischenprodukte zu ihrer Herstellung und sie enthaltende Mittel
JP2000505058A (ja)	2000-04-25	フェニル酢酸誘導体、その製造、その製造用中間体、及びそれからなる組成物