SK107597A3 - Fungicidal aza-heterocycloalkenes, producing method thereof, agents for killing the pests containing the same, method of killing the pests and use said compounds - Google Patents
Fungicidal aza-heterocycloalkenes, producing method thereof, agents for killing the pests containing the same, method of killing the pests and use said compounds Download PDFInfo
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- SK107597A3 SK107597A3 SK1075-97A SK107597A SK107597A3 SK 107597 A3 SK107597 A3 SK 107597A3 SK 107597 A SK107597 A SK 107597A SK 107597 A3 SK107597 A3 SK 107597A3
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- cyano
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 53
- 238000000034 method Methods 0.000 title claims description 41
- 230000000855 fungicidal effect Effects 0.000 title claims description 13
- 241000607479 Yersinia pestis Species 0.000 title claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
- 239000001301 oxygen Substances 0.000 claims abstract description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000005549 heteroarylene group Chemical group 0.000 claims abstract description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 7
- -1 3-aza-1-propene-2,3-diyl Chemical group 0.000 claims description 420
- 125000004432 carbon atom Chemical group C* 0.000 claims description 94
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 84
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 69
- 239000000460 chlorine Substances 0.000 claims description 66
- 229910052717 sulfur Inorganic materials 0.000 claims description 58
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 54
- 229910052801 chlorine Inorganic materials 0.000 claims description 53
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 52
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 51
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 50
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 50
- 239000011737 fluorine Substances 0.000 claims description 48
- 229910052731 fluorine Inorganic materials 0.000 claims description 48
- 125000004434 sulfur atom Chemical group 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 47
- 125000003545 alkoxy group Chemical group 0.000 claims description 39
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 38
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 150000002367 halogens Chemical class 0.000 claims description 32
- 125000005843 halogen group Chemical group 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 30
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 29
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 28
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 28
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 28
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 28
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 27
- 238000002360 preparation method Methods 0.000 claims description 26
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 25
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 22
- 229910052794 bromium Inorganic materials 0.000 claims description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 20
- 125000003282 alkyl amino group Chemical group 0.000 claims description 20
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 18
- 125000004414 alkyl thio group Chemical group 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 16
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 16
- 125000001153 fluoro group Chemical group F* 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 125000001188 haloalkyl group Chemical group 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 14
- 125000000335 thiazolyl group Chemical group 0.000 claims description 14
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 13
- 125000003277 amino group Chemical group 0.000 claims description 13
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 150000002440 hydroxy compounds Chemical class 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 10
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
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- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 9
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- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 9
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- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 7
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
- 125000001246 bromo group Chemical group Br* 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 7
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims description 6
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 6
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 6
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000004957 naphthylene group Chemical group 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 5
- 125000005700 haloalkyleneoxy group Chemical group 0.000 claims description 5
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 5
- 125000002950 monocyclic group Chemical group 0.000 claims description 5
- 239000003208 petroleum Substances 0.000 claims description 5
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims description 4
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical group CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
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- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
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- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 4
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims description 4
- 125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 4
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- 125000006413 ring segment Chemical group 0.000 claims description 4
- 125000005649 substituted arylene group Chemical group 0.000 claims description 4
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
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- 125000006351 ethylthiomethyl group Chemical group [H]C([H])([H])C([H])([H])SC([H])([H])* 0.000 claims description 3
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- 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
- 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims description 2
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
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- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 2
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 claims 1
- OFZBXMLLITZCRS-UHFFFAOYSA-N CCOC(CN(NC)SCC)SC Chemical compound CCOC(CN(NC)SCC)SC OFZBXMLLITZCRS-UHFFFAOYSA-N 0.000 claims 1
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- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/88—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with three ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
- C07D273/04—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D291/00—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms
- C07D291/02—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms not condensed with other rings
- C07D291/06—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D419/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms
- C07D419/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D419/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D419/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms
- C07D419/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19504625 | 1995-02-13 | ||
DE19510297A DE19510297A1 (de) | 1995-02-13 | 1995-03-22 | Substituierte Heterocycloalkene |
PCT/EP1996/000384 WO1996025406A1 (de) | 1995-02-13 | 1996-01-31 | Fungizide aza-heterocycloalkene |
Publications (1)
Publication Number | Publication Date |
---|---|
SK107597A3 true SK107597A3 (en) | 1998-02-04 |
Family
ID=26012371
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SK1075-97A SK107597A3 (en) | 1995-02-13 | 1996-01-31 | Fungicidal aza-heterocycloalkenes, producing method thereof, agents for killing the pests containing the same, method of killing the pests and use said compounds |
Country Status (16)
Country | Link |
---|---|
US (2) | US6214825B1 (hu) |
EP (1) | EP0809637B1 (hu) |
JP (1) | JPH11500717A (hu) |
CN (1) | CN1181076A (hu) |
AT (1) | ATE242224T1 (hu) |
AU (1) | AU4539396A (hu) |
BR (1) | BR9606955A (hu) |
CA (1) | CA2212683A1 (hu) |
CZ (1) | CZ253397A3 (hu) |
HU (1) | HUP9702456A3 (hu) |
IL (1) | IL117097A0 (hu) |
MX (1) | MX9706142A (hu) |
PL (1) | PL321757A1 (hu) |
SK (1) | SK107597A3 (hu) |
TR (1) | TR199700790T1 (hu) |
WO (1) | WO1996025406A1 (hu) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19642864A1 (de) * | 1996-10-17 | 1998-04-23 | Bayer Ag | Oximderivate |
ID24435A (id) * | 1997-08-14 | 2000-07-20 | Bayer Ag | Metoksiminometiloksadiazina |
DE19745376A1 (de) | 1997-10-14 | 1999-04-15 | Bayer Ag | Thiomide |
DE19810018A1 (de) | 1998-03-09 | 1999-09-16 | Bayer Ag | Benzoheterocyclyloxime |
DE19819828A1 (de) * | 1998-05-04 | 1999-11-11 | Bayer Ag | Methoximinomethyloxathiazine |
EP2922823B1 (en) | 2012-11-20 | 2018-10-31 | Merck Sharp & Dohme Corp. | Pyrimidine pde10 inhibitors |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA1273921A (en) | 1982-09-28 | 1990-09-11 | Walter G. Brouwer | 3-aryl-5, 6-dihydro-1, 4, 2-oxathiazines and their oxides |
GB9307247D0 (en) * | 1993-04-07 | 1993-06-02 | Zeneca Ltd | Fungicidal compounds |
DE4408005A1 (de) | 1993-08-11 | 1995-02-16 | Bayer Ag | Substituierte Azadioxacycloalkene |
CA2186947A1 (en) * | 1994-04-01 | 1995-10-12 | Kazuo Ueda | Oxime derivative and bactericide containing the same as active ingredients |
DE19819828A1 (de) * | 1998-05-04 | 1999-11-11 | Bayer Ag | Methoximinomethyloxathiazine |
-
1996
- 1996-01-31 BR BR9606955A patent/BR9606955A/pt not_active Application Discontinuation
- 1996-01-31 HU HU9702456A patent/HUP9702456A3/hu unknown
- 1996-01-31 PL PL96321757A patent/PL321757A1/xx unknown
- 1996-01-31 AU AU45393/96A patent/AU4539396A/en not_active Abandoned
- 1996-01-31 SK SK1075-97A patent/SK107597A3/sk unknown
- 1996-01-31 US US08/875,908 patent/US6214825B1/en not_active Expired - Fee Related
- 1996-01-31 WO PCT/EP1996/000384 patent/WO1996025406A1/de active IP Right Grant
- 1996-01-31 JP JP8524610A patent/JPH11500717A/ja not_active Ceased
- 1996-01-31 MX MX9706142A patent/MX9706142A/es unknown
- 1996-01-31 TR TR97/00790T patent/TR199700790T1/xx unknown
- 1996-01-31 CN CN96193205A patent/CN1181076A/zh active Pending
- 1996-01-31 AT AT96901336T patent/ATE242224T1/de not_active IP Right Cessation
- 1996-01-31 EP EP96901336A patent/EP0809637B1/de not_active Expired - Lifetime
- 1996-01-31 CZ CZ972533A patent/CZ253397A3/cs unknown
- 1996-01-31 CA CA002212683A patent/CA2212683A1/en not_active Abandoned
- 1996-02-09 IL IL11709796A patent/IL117097A0/xx unknown
-
2000
- 2000-10-31 US US09/702,551 patent/US6407098B1/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
MX9706142A (es) | 1997-11-29 |
WO1996025406A1 (de) | 1996-08-22 |
US6214825B1 (en) | 2001-04-10 |
TR199700790T1 (xx) | 1998-02-21 |
PL321757A1 (en) | 1997-12-22 |
BR9606955A (pt) | 1997-10-28 |
US6407098B1 (en) | 2002-06-18 |
CN1181076A (zh) | 1998-05-06 |
HUP9702456A3 (en) | 2000-06-28 |
ATE242224T1 (de) | 2003-06-15 |
EP0809637B1 (de) | 2003-06-04 |
HUP9702456A2 (hu) | 1998-03-30 |
CZ253397A3 (en) | 1997-11-12 |
IL117097A0 (en) | 1996-06-18 |
EP0809637A1 (de) | 1997-12-03 |
JPH11500717A (ja) | 1999-01-19 |
AU4539396A (en) | 1996-09-04 |
CA2212683A1 (en) | 1996-08-22 |
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