CA2230031A1 - 4,4-difluoro-3-butenylester derivatives or 4,4-difluoro-3-halogen-3-butenylester derivatives and the use thereof as pesticides - Google Patents
4,4-difluoro-3-butenylester derivatives or 4,4-difluoro-3-halogen-3-butenylester derivatives and the use thereof as pesticides Download PDFInfo
- Publication number
- CA2230031A1 CA2230031A1 CA002230031A CA2230031A CA2230031A1 CA 2230031 A1 CA2230031 A1 CA 2230031A1 CA 002230031 A CA002230031 A CA 002230031A CA 2230031 A CA2230031 A CA 2230031A CA 2230031 A1 CA2230031 A1 CA 2230031A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- spp
- alkoxy
- optionally
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000000575 pesticide Substances 0.000 title claims 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 54
- 238000000034 method Methods 0.000 claims abstract description 26
- 150000002148 esters Chemical class 0.000 claims abstract description 21
- 229910052736 halogen Chemical group 0.000 claims abstract description 19
- 150000002367 halogens Chemical group 0.000 claims abstract description 19
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 238000004519 manufacturing process Methods 0.000 claims abstract 3
- -1 cyano, trimethylsilyl Chemical group 0.000 claims description 82
- 150000001875 compounds Chemical class 0.000 claims description 78
- 150000002431 hydrogen Chemical class 0.000 claims description 44
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 29
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 19
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
- 125000004414 alkyl thio group Chemical group 0.000 claims description 16
- 150000001408 amides Chemical class 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 150000007970 thio esters Chemical class 0.000 claims description 14
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 13
- 150000007513 acids Chemical class 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 13
- 125000001931 aliphatic group Chemical group 0.000 claims description 12
- 239000003085 diluting agent Substances 0.000 claims description 12
- 239000002585 base Substances 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 150000003573 thiols Chemical class 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 10
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000003107 substituted aryl group Chemical group 0.000 claims description 9
- 101100440695 Dictyostelium discoideum corB gene Proteins 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 229910006069 SO3H Inorganic materials 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 239000005864 Sulphur Substances 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- LIIBSISAILMKHT-UHFFFAOYSA-N 1-fluorobut-1-en-1-ol Chemical compound CCC=C(O)F LIIBSISAILMKHT-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- 150000008065 acid anhydrides Chemical class 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 150000001413 amino acids Chemical class 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- 239000004606 Fillers/Extenders Substances 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 5
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 5
- 150000001735 carboxylic acids Chemical class 0.000 claims 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 101100212791 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) YBL068W-A gene Proteins 0.000 claims 1
- NFGODEMQGQNUKK-UHFFFAOYSA-M [6-(diethylamino)-9-(2-octadecoxycarbonylphenyl)xanthen-3-ylidene]-diethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C1=C2C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C21 NFGODEMQGQNUKK-UHFFFAOYSA-M 0.000 claims 1
- 229910001413 alkali metal ion Inorganic materials 0.000 claims 1
- JYNZIOFUHBJABQ-UHFFFAOYSA-N allyl-{6-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-hexyl-}-methyl-amin Chemical group C=1OC2=CC(OCCCCCCN(C)CC=C)=CC=C2C=1C1=CC=C(Br)C=C1 JYNZIOFUHBJABQ-UHFFFAOYSA-N 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 241001465754 Metazoa Species 0.000 abstract description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- 239000000203 mixture Substances 0.000 description 25
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- 150000003254 radicals Chemical class 0.000 description 18
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 230000000694 effects Effects 0.000 description 15
- 239000002904 solvent Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
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- 238000009472 formulation Methods 0.000 description 11
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- 241000244206 Nematoda Species 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
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- 238000000921 elemental analysis Methods 0.000 description 5
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
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- PCYKQGRAPGQQCB-UHFFFAOYSA-N 3,4,4-trifluorobut-3-en-1-ol Chemical compound OCCC(F)=C(F)F PCYKQGRAPGQQCB-UHFFFAOYSA-N 0.000 description 3
- GQCQMFYIFUDARF-UHFFFAOYSA-N 4-bromo-1,1,2-trifluorobut-1-ene Chemical compound FC(F)=C(F)CCBr GQCQMFYIFUDARF-UHFFFAOYSA-N 0.000 description 3
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C229/56—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in ortho-position
-
- 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
-
- 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
- A01N47/08—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 one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/20—N-Aryl derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/77—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing carboxyl groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/88—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Manufacturing Of Micro-Capsules (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US327995P | 1995-08-25 | 1995-08-25 | |
DE1995131276 DE19531276A1 (de) | 1995-08-25 | 1995-08-25 | Arylester |
US60/003,279 | 1995-08-25 | ||
DE19531276.7 | 1995-08-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2230031A1 true CA2230031A1 (en) | 1997-03-06 |
Family
ID=26017988
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002230031A Abandoned CA2230031A1 (en) | 1995-08-25 | 1996-08-13 | 4,4-difluoro-3-butenylester derivatives or 4,4-difluoro-3-halogen-3-butenylester derivatives and the use thereof as pesticides |
Country Status (9)
Country | Link |
---|---|
EP (1) | EP0846099A1 (zh) |
JP (1) | JPH11510474A (zh) |
KR (1) | KR19990044035A (zh) |
CN (1) | CN1200108A (zh) |
AU (1) | AU6872896A (zh) |
BR (1) | BR9610022A (zh) |
CA (1) | CA2230031A1 (zh) |
TR (1) | TR199800296T1 (zh) |
WO (1) | WO1997008130A1 (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20220104495A1 (en) * | 2019-01-30 | 2022-04-07 | Isagro S.P.A. | Theophylline derivatives with nematocidal activity, their agronomic compositions and relative use |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19922934A1 (de) * | 1999-05-19 | 2000-11-23 | Bayer Ag | Neue Halogenverbindungen |
AU2160201A (en) * | 1999-11-19 | 2001-05-30 | Novartis Ag | Organic compounds and their use in the control of ectoparasites |
DE60228111D1 (de) * | 2001-09-28 | 2008-09-18 | Kumiai Chemical Industry Co | Difluoralkenderivat, dieses enthaltende mittel zur bekämpfung von schädlingen und zwischenprodukt dafür |
JPWO2003042153A1 (ja) * | 2001-11-15 | 2005-03-10 | クミアイ化学工業株式会社 | ジフルオロアルケン誘導体及びそれを含有する有害生物防除剤 |
AU2003252536A1 (en) * | 2002-08-01 | 2004-02-23 | Basf Aktiengesellschaft | Pesticidal fluoroalkene derivatives |
US9526242B2 (en) * | 2013-07-18 | 2016-12-27 | Fmc Corporation | Nematode repellent composition |
CN113912495A (zh) * | 2020-07-09 | 2022-01-11 | 山东省联合农药工业有限公司 | 一种含氟丁烯酯类衍生物及其制备方法与用途 |
AR123594A1 (es) | 2020-09-26 | 2022-12-21 | Pi Industries Ltd | Compuestos nematicidas y uso de los mismos |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4952580A (en) * | 1985-06-20 | 1990-08-28 | Fmc Corporation | Pesticidal polyhaloalkene derivatives |
US4950666A (en) * | 1989-03-30 | 1990-08-21 | Fmc Corporation | Difluoroalkane and difluoroalkenylalkane pesticides |
DE3941966A1 (de) * | 1989-12-15 | 1991-06-20 | Schering Ag | Halogenierte olefine, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
DE4445792A1 (de) * | 1994-12-21 | 1996-06-27 | Bayer Ag | Fluorbutenyl(thio)ether |
-
1996
- 1996-08-13 TR TR1998/00296T patent/TR199800296T1/xx unknown
- 1996-08-13 BR BR9610022A patent/BR9610022A/pt not_active Application Discontinuation
- 1996-08-13 JP JP8531289A patent/JPH11510474A/ja active Pending
- 1996-08-13 EP EP96929246A patent/EP0846099A1/de not_active Ceased
- 1996-08-13 CN CN96197628A patent/CN1200108A/zh active Pending
- 1996-08-13 AU AU68728/96A patent/AU6872896A/en not_active Abandoned
- 1996-08-13 CA CA002230031A patent/CA2230031A1/en not_active Abandoned
- 1996-08-13 KR KR1019980701267A patent/KR19990044035A/ko not_active Application Discontinuation
- 1996-08-13 WO PCT/EP1996/003569 patent/WO1997008130A1/de not_active Application Discontinuation
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20220104495A1 (en) * | 2019-01-30 | 2022-04-07 | Isagro S.P.A. | Theophylline derivatives with nematocidal activity, their agronomic compositions and relative use |
Also Published As
Publication number | Publication date |
---|---|
WO1997008130A1 (de) | 1997-03-06 |
TR199800296T1 (xx) | 1998-06-22 |
AU6872896A (en) | 1997-03-19 |
EP0846099A1 (de) | 1998-06-10 |
KR19990044035A (ko) | 1999-06-25 |
CN1200108A (zh) | 1998-11-25 |
BR9610022A (pt) | 1999-07-06 |
JPH11510474A (ja) | 1999-09-14 |
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