EA003995B1 - Производные 1-арил- и пиридилпиразола с пестицидными свойствами - Google Patents
Производные 1-арил- и пиридилпиразола с пестицидными свойствами Download PDFInfo
- Publication number
- EA003995B1 EA003995B1 EA199900598A EA199900598A EA003995B1 EA 003995 B1 EA003995 B1 EA 003995B1 EA 199900598 A EA199900598 A EA 199900598A EA 199900598 A EA199900598 A EA 199900598A EA 003995 B1 EA003995 B1 EA 003995B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- alkyl
- formula
- compound
- amino
- trifluoromethylphenyl
- Prior art date
Links
- 230000000361 pesticidal effect Effects 0.000 title claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 173
- -1 1H-pyrazol-1-yl Chemical group 0.000 claims abstract description 124
- 239000000203 mixture Substances 0.000 claims abstract description 101
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 87
- 238000000034 method Methods 0.000 claims abstract description 50
- 150000003839 salts Chemical class 0.000 claims abstract description 41
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 39
- 241001465754 Metazoa Species 0.000 claims abstract description 35
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 34
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 32
- 150000002367 halogens Chemical class 0.000 claims abstract description 32
- 241000238631 Hexapoda Species 0.000 claims abstract description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 26
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 24
- 125000004961 1-arylpyrazolyl group Chemical group 0.000 claims abstract description 21
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 20
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 15
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims abstract description 13
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 13
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims abstract description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 12
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 11
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 11
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 claims abstract description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 9
- 125000003277 amino group Chemical group 0.000 claims abstract description 8
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 241000251539 Vertebrata <Metazoa> Species 0.000 claims abstract description 7
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims abstract description 7
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims abstract description 7
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract description 6
- 230000037396 body weight Effects 0.000 claims abstract description 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 6
- XPEOQIUFBJRCKE-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfanylpyrazole-3-carbothioamide Chemical compound N1=C(C(N)=S)C(SC)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl XPEOQIUFBJRCKE-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 5
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 4
- XGQWFTJEQSVRCK-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfanyl)pyrazole-3-carbothioamide Chemical compound NC1=C(SC(F)(F)F)C(C(=S)N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl XGQWFTJEQSVRCK-UHFFFAOYSA-N 0.000 claims abstract description 4
- 230000029936 alkylation Effects 0.000 claims abstract description 4
- 238000005804 alkylation reaction Methods 0.000 claims abstract description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract description 4
- 125000003435 aroyl group Chemical group 0.000 claims abstract description 4
- YZDYMQLXPYEYJF-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethoxy)phenyl]-4-ethylsulfinylpyrazole-3-carbothioamide Chemical compound N1=C(C(N)=S)C(S(=O)CC)=C(N)N1C1=C(Cl)C=C(OC(F)(F)F)C=C1Cl YZDYMQLXPYEYJF-UHFFFAOYSA-N 0.000 claims abstract description 3
- LNWUAHJAKNEAMP-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethoxy)phenyl]-4-methylsulfinylpyrazole-3-carbothioamide Chemical compound N1=C(C(N)=S)C(S(=O)C)=C(N)N1C1=C(Cl)C=C(OC(F)(F)F)C=C1Cl LNWUAHJAKNEAMP-UHFFFAOYSA-N 0.000 claims abstract description 3
- PNTBJOMCNZIYCO-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-ethylsulfinylpyrazole-3-carbothioamide Chemical compound N1=C(C(N)=S)C(S(=O)CC)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl PNTBJOMCNZIYCO-UHFFFAOYSA-N 0.000 claims abstract description 3
- KTYPGSIQGATQBH-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazole-3-carbothioamide Chemical compound N1=C(C(N)=S)C(S(=O)C)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl KTYPGSIQGATQBH-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000006519 CCH3 Chemical group 0.000 claims abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000006627 ethoxycarbonylamino group Chemical group 0.000 claims abstract description 3
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims abstract description 3
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims abstract description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims abstract description 3
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 3
- 230000003647 oxidation Effects 0.000 claims abstract 3
- 238000007254 oxidation reaction Methods 0.000 claims abstract 3
- CICWDLGVJKMEIX-UHFFFAOYSA-N 5-amino-1-[2-bromo-6-chloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazole-3-carbothioamide Chemical compound N1=C(C(N)=S)C(S(=O)C)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Br CICWDLGVJKMEIX-UHFFFAOYSA-N 0.000 claims abstract 2
- LTLCKYCNOOXPKO-UHFFFAOYSA-N 5-amino-1-[2-chloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazole-3-carbothioamide Chemical compound N1=C(C(N)=S)C(S(=O)C)=C(N)N1C1=CC=C(C(F)(F)F)C=C1Cl LTLCKYCNOOXPKO-UHFFFAOYSA-N 0.000 claims abstract 2
- 230000032050 esterification Effects 0.000 claims abstract 2
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- 230000001590 oxidative effect Effects 0.000 claims description 3
- VWHMZLMRNVXPFA-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfonylpyrazole-3-carbothioamide Chemical compound N1=C(C(N)=S)C(S(=O)(=O)C)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl VWHMZLMRNVXPFA-UHFFFAOYSA-N 0.000 claims description 2
- ZTOXNAIRALLYRB-UHFFFAOYSA-N 5-amino-1-[2-bromo-6-chloro-4-(trifluoromethyl)phenyl]-4-ethylsulfinylpyrazole-3-carbothioamide Chemical compound N1=C(C(N)=S)C(S(=O)CC)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Br ZTOXNAIRALLYRB-UHFFFAOYSA-N 0.000 claims description 2
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- 150000001879 copper Chemical class 0.000 claims description 2
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- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
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- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
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- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
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- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical class NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
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- 239000012414 tert-butyl nitrite Substances 0.000 description 1
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
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- 150000003573 thiols Chemical class 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
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
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- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
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)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3388596P | 1996-12-24 | 1996-12-24 | |
| PCT/EP1997/007116 WO1998028279A1 (en) | 1996-12-24 | 1997-12-18 | Pesticidal 1-aryl and pyridylpyrazole derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA199900598A1 EA199900598A1 (ru) | 2000-02-28 |
| EA003995B1 true EA003995B1 (ru) | 2003-12-25 |
Family
ID=21873029
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA199900598A EA003995B1 (ru) | 1996-12-24 | 1997-12-18 | Производные 1-арил- и пиридилпиразола с пестицидными свойствами |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0948487A1 (cs) |
| JP (1) | JP2001506665A (cs) |
| KR (1) | KR20000062318A (cs) |
| AP (1) | AP1004A (cs) |
| AU (1) | AU747450B2 (cs) |
| BG (1) | BG103592A (cs) |
| BR (1) | BR9714086A (cs) |
| CA (1) | CA2275634A1 (cs) |
| CZ (1) | CZ229999A3 (cs) |
| EA (1) | EA003995B1 (cs) |
| HU (1) | HUP0000464A3 (cs) |
| ID (1) | ID22807A (cs) |
| IL (1) | IL130537A (cs) |
| NZ (1) | NZ336420A (cs) |
| PL (1) | PL334237A1 (cs) |
| SK (1) | SK284351B6 (cs) |
| TR (1) | TR199901471T2 (cs) |
| UA (1) | UA67734C2 (cs) |
| WO (1) | WO1998028279A1 (cs) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| US8791046B2 (en) | 2006-11-10 | 2014-07-29 | Basf Se | Crystalline modification of fipronil |
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| US8097562B2 (en) | 2006-11-30 | 2012-01-17 | Basf Se | Agrochemical formulations comprising N-vinylamid co-polymers |
| JP5290188B2 (ja) | 2006-11-30 | 2013-09-18 | ビーエーエスエフ ソシエタス・ヨーロピア | ジイソシアネートをベースとしたコポリマーを含む農薬製剤 |
| EP2258177A3 (en) | 2006-12-15 | 2011-11-09 | Rohm and Haas Company | Mixtures comprising 1-methylcyclopropene |
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| CN101589030A (zh) | 2007-01-26 | 2009-11-25 | 巴斯夫欧洲公司 | 用于对抗动物害虫的3-氨基-1,2-苯并异噻唑化合物ⅱ |
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| WO2008095924A2 (de) | 2007-02-06 | 2008-08-14 | Basf Se | Insektizide als safener für fungizide mit phytotoxischer wirkung |
| WO2008125410A2 (en) | 2007-04-12 | 2008-10-23 | Basf Se | Pesticidal mixtures comprising cyanosulfoximine compounds |
| EP2076602A2 (en) | 2007-04-23 | 2009-07-08 | Basf Se | Plant produtivity enhancement by combining chemical agents with transgenic modifications |
| PL2180783T3 (pl) | 2007-08-16 | 2017-08-31 | Basf Se | Kompozycje i sposoby d o zaprawiania nasion |
| NZ599174A (en) | 2007-09-20 | 2012-08-31 | Basf Se | Combinations comprising a fungicidal strain and an azolopyrimidin-7-ylamine |
| US20100311582A1 (en) | 2008-01-25 | 2010-12-09 | Syngenta Crop Protection, Inc. | Chemical compounds |
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| ES2444270T3 (es) | 2009-03-04 | 2014-02-24 | Basf Se | Compuestos de 3-arilquinazolin-3-ona para combatir plagas de invertebrados |
| WO2011003796A1 (en) | 2009-07-06 | 2011-01-13 | Basf Se | Pyridazine compounds for controlling invertebrate pests |
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| GB8713768D0 (en) * | 1987-06-12 | 1987-07-15 | May & Baker Ltd | Compositions of matter |
| US5232940A (en) * | 1985-12-20 | 1993-08-03 | Hatton Leslie R | Derivatives of N-phenylpyrazoles |
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| AU1191292A (en) * | 1991-02-11 | 1992-09-07 | Schering Agrochemicals Limited | Imidazole pesticides |
| GB9120641D0 (en) * | 1991-09-27 | 1991-11-06 | Ici Plc | Heterocyclic compounds |
| GB9306184D0 (en) * | 1993-03-25 | 1993-05-19 | Zeneca Ltd | Heteroaromatic compounds |
| DE4343832A1 (de) * | 1993-12-22 | 1995-06-29 | Bayer Ag | Substituierte 1-Arylpyrazole |
| DE19511269A1 (de) * | 1994-03-30 | 1995-10-05 | Ciba Geigy Ag | Pyrazole |
| DE4414333A1 (de) * | 1994-04-25 | 1995-10-26 | Bayer Ag | Substituierte Pyridylpyrazole |
| US6350771B1 (en) * | 1996-12-24 | 2002-02-26 | Rhone-Poulenc, Inc. | Pesticidal 1-arylpyrazoles |
-
1997
- 1997-12-18 AP APAP/P/1999/001586A patent/AP1004A/en active
- 1997-12-18 NZ NZ336420A patent/NZ336420A/en unknown
- 1997-12-18 BR BR9714086-4A patent/BR9714086A/pt unknown
- 1997-12-18 WO PCT/EP1997/007116 patent/WO1998028279A1/en not_active Application Discontinuation
- 1997-12-18 CA CA002275634A patent/CA2275634A1/en not_active Abandoned
- 1997-12-18 PL PL97334237A patent/PL334237A1/xx unknown
- 1997-12-18 EA EA199900598A patent/EA003995B1/ru not_active IP Right Cessation
- 1997-12-18 TR TR1999/01471T patent/TR199901471T2/xx unknown
- 1997-12-18 HU HU0000464A patent/HUP0000464A3/hu unknown
- 1997-12-18 ID IDW990586A patent/ID22807A/id unknown
- 1997-12-18 JP JP52835198A patent/JP2001506665A/ja active Pending
- 1997-12-18 SK SK856-99A patent/SK284351B6/sk not_active IP Right Cessation
- 1997-12-18 CZ CZ992299A patent/CZ229999A3/cs unknown
- 1997-12-18 IL IL13053797A patent/IL130537A/en not_active IP Right Cessation
- 1997-12-18 KR KR1019997005757A patent/KR20000062318A/ko not_active Abandoned
- 1997-12-18 EP EP97953851A patent/EP0948487A1/en not_active Ceased
- 1997-12-18 UA UA99074126A patent/UA67734C2/uk unknown
- 1997-12-18 AU AU57598/98A patent/AU747450B2/en not_active Ceased
-
1999
- 1999-07-19 BG BG103592A patent/BG103592A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| UA67734C2 (uk) | 2004-07-15 |
| SK85699A3 (en) | 2000-01-18 |
| ID22807A (id) | 1999-12-09 |
| AU5759898A (en) | 1998-07-17 |
| NZ336420A (en) | 2001-04-27 |
| EP0948487A1 (en) | 1999-10-13 |
| JP2001506665A (ja) | 2001-05-22 |
| IL130537A (en) | 2004-08-31 |
| IL130537A0 (en) | 2000-06-01 |
| PL334237A1 (en) | 2000-02-14 |
| WO1998028279A1 (en) | 1998-07-02 |
| SK284351B6 (sk) | 2005-02-04 |
| CZ229999A3 (cs) | 1999-11-17 |
| HUP0000464A3 (en) | 2002-01-28 |
| HUP0000464A2 (hu) | 2000-06-28 |
| TR199901471T2 (xx) | 1999-10-21 |
| KR20000062318A (ko) | 2000-10-25 |
| CA2275634A1 (en) | 1998-07-02 |
| AP9901586A0 (en) | 1999-06-30 |
| EA199900598A1 (ru) | 2000-02-28 |
| AP1004A (en) | 2001-08-28 |
| BR9714086A (pt) | 2000-05-09 |
| BG103592A (en) | 2000-11-30 |
| AU747450B2 (en) | 2002-05-16 |
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| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
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| MK4A | Patent expired |
Designated state(s): RU |