DE10118310A1 - Hetarylsubstituierte carbocyclische 1,3-Dione - Google Patents
Hetarylsubstituierte carbocyclische 1,3-DioneInfo
- Publication number
- DE10118310A1 DE10118310A1 DE10118310A DE10118310A DE10118310A1 DE 10118310 A1 DE10118310 A1 DE 10118310A1 DE 10118310 A DE10118310 A DE 10118310A DE 10118310 A DE10118310 A DE 10118310A DE 10118310 A1 DE10118310 A1 DE 10118310A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- compounds
- formula
- given above
- het
- 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.)
- Withdrawn
Links
- 239000000417 fungicide Substances 0.000 title claims description 19
- 239000004009 herbicide Substances 0.000 title claims description 17
- 239000000575 pesticide Substances 0.000 title claims description 6
- 239000002917 insecticide Substances 0.000 title description 15
- 239000000642 acaricide Substances 0.000 title description 7
- 239000002519 antifouling agent Substances 0.000 title description 6
- 239000005645 nematicide Substances 0.000 title description 6
- 239000013057 ectoparasiticide Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 67
- 238000002360 preparation method Methods 0.000 claims abstract description 54
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 47
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 38
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 34
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 23
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 22
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 17
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 13
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 12
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
- 229910052751 metal Inorganic materials 0.000 claims abstract description 8
- 239000002184 metal Substances 0.000 claims abstract description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 7
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 6
- 125000006413 ring segment Chemical group 0.000 claims abstract description 6
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims abstract description 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 4
- 125000005108 alkenylthio group Chemical group 0.000 claims abstract description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 145
- -1 polyalkoxyalkyl Chemical group 0.000 claims description 139
- 238000000034 method Methods 0.000 claims description 87
- 230000008569 process Effects 0.000 claims description 63
- 239000003085 diluting agent Substances 0.000 claims description 54
- 239000002253 acid Substances 0.000 claims description 53
- 229910052736 halogen Inorganic materials 0.000 claims description 50
- 239000001257 hydrogen Substances 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 49
- 150000002367 halogens Chemical group 0.000 claims description 47
- 239000011230 binding agent Substances 0.000 claims description 41
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 33
- 239000001301 oxygen Substances 0.000 claims description 33
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 30
- 239000011593 sulfur Substances 0.000 claims description 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 21
- 125000000335 thiazolyl group Chemical group 0.000 claims description 18
- 125000001188 haloalkyl group Chemical group 0.000 claims description 17
- 241000607479 Yersinia pestis Species 0.000 claims description 13
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 13
- 241000233866 Fungi Species 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 239000013543 active substance Substances 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 10
- 241001465754 Metazoa Species 0.000 claims description 9
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 9
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 8
- 239000004606 Fillers/Extenders Substances 0.000 claims description 7
- 150000004820 halides Chemical class 0.000 claims description 7
- 229920006395 saturated elastomer Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical class OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 229910021645 metal ion Inorganic materials 0.000 claims description 5
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 5
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 4
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
- 150000003018 phosphorus compounds Chemical class 0.000 claims description 4
- NBYQXBYMEUOBON-UHFFFAOYSA-N carbamothioyl chloride Chemical class NC(Cl)=S NBYQXBYMEUOBON-UHFFFAOYSA-N 0.000 claims description 3
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 3
- 230000008635 plant growth Effects 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- LRYSUGTXBIPBGB-UHFFFAOYSA-N chloromethanedithioic acid Chemical class SC(Cl)=S LRYSUGTXBIPBGB-UHFFFAOYSA-N 0.000 claims description 2
- 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 2
- 150000002540 isothiocyanates Chemical class 0.000 claims description 2
- 150000002736 metal compounds Chemical class 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 235000001674 Agaricus brunnescens Nutrition 0.000 claims 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract description 2
- 125000003118 aryl group Chemical group 0.000 abstract description 2
- 125000001425 triazolyl group Chemical group 0.000 abstract description 2
- 125000005843 halogen group Chemical group 0.000 abstract 14
- 125000005429 oxyalkyl group Chemical group 0.000 abstract 1
- 125000004001 thioalkyl group Chemical group 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 100
- 239000004480 active ingredient Substances 0.000 description 85
- 239000002904 solvent Substances 0.000 description 63
- 239000000203 mixture Substances 0.000 description 62
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 60
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
- SQQWBSBBCSFQGC-JLHYYAGUSA-N ubiquinone-2 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CCC=C(C)C)=C(C)C1=O SQQWBSBBCSFQGC-JLHYYAGUSA-N 0.000 description 43
- 239000003995 emulsifying agent Substances 0.000 description 41
- 239000000460 chlorine Substances 0.000 description 40
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 37
- 229910052801 chlorine Inorganic materials 0.000 description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- 239000011737 fluorine Substances 0.000 description 34
- 229910052731 fluorine Inorganic materials 0.000 description 34
- 150000002431 hydrogen Chemical class 0.000 description 32
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 31
- 238000006243 chemical reaction Methods 0.000 description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 239000000243 solution Substances 0.000 description 30
- 239000000126 substance Substances 0.000 description 30
- 238000012360 testing method Methods 0.000 description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 25
- 238000009472 formulation Methods 0.000 description 25
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 23
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 23
- 229910052794 bromium Inorganic materials 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 239000000463 material Substances 0.000 description 20
- 239000012141 concentrate Substances 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- 230000000694 effects Effects 0.000 description 18
- 125000001153 fluoro group Chemical group F* 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 18
- 239000008187 granular material Substances 0.000 description 17
- 239000000843 powder Substances 0.000 description 17
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 16
- 125000002877 alkyl aryl group Chemical group 0.000 description 16
- 239000002585 base Substances 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 16
- 150000002148 esters Chemical class 0.000 description 16
- 229920000151 polyglycol Polymers 0.000 description 16
- 239000010695 polyglycol Substances 0.000 description 16
- 150000002170 ethers Chemical class 0.000 description 15
- 239000002689 soil Substances 0.000 description 15
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- 239000011734 sodium Substances 0.000 description 14
- 229910052708 sodium Inorganic materials 0.000 description 14
- 239000007858 starting material Substances 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 241000238631 Hexapoda Species 0.000 description 13
- 230000001965 increasing effect Effects 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 239000002023 wood Substances 0.000 description 13
- 240000008042 Zea mays Species 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 11
- 244000005700 microbiome Species 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 239000000969 carrier Substances 0.000 description 10
- 235000019441 ethanol Nutrition 0.000 description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000975 dye Substances 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 235000011181 potassium carbonates Nutrition 0.000 description 9
- 230000001681 protective effect Effects 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 238000005507 spraying Methods 0.000 description 9
- 241000238876 Acari Species 0.000 description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 8
- 235000010469 Glycine max Nutrition 0.000 description 8
- 150000001340 alkali metals Chemical class 0.000 description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 8
- 239000010949 copper Substances 0.000 description 8
- 229910052802 copper Inorganic materials 0.000 description 8
- 239000002270 dispersing agent Substances 0.000 description 8
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 8
- 239000002480 mineral oil Substances 0.000 description 8
- 150000002825 nitriles Chemical class 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 239000003973 paint Substances 0.000 description 8
- 239000011435 rock Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 239000011877 solvent mixture Substances 0.000 description 8
- 241000219146 Gossypium Species 0.000 description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 150000001721 carbon Chemical group 0.000 description 7
- 229940113088 dimethylacetamide Drugs 0.000 description 7
- 239000006072 paste Substances 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 7
- 238000012545 processing Methods 0.000 description 7
- 108090000623 proteins and genes Proteins 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical class 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 240000007124 Brassica oleracea Species 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 6
- 230000000895 acaricidal effect Effects 0.000 description 6
- 239000000853 adhesive Substances 0.000 description 6
- 230000001070 adhesive effect Effects 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 230000006378 damage Effects 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- 230000018109 developmental process Effects 0.000 description 6
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Aalpha Natural products C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- 235000009973 maize Nutrition 0.000 description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 6
- 239000002798 polar solvent Substances 0.000 description 6
- 239000011591 potassium Substances 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- 125000004076 pyridyl group Chemical group 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 241000894007 species Species 0.000 description 6
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
- 230000009261 transgenic effect Effects 0.000 description 6
- KAATUXNTWXVJKI-NSHGMRRFSA-N (1R)-cis-(alphaS)-cypermethrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-NSHGMRRFSA-N 0.000 description 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 5
- 125000006552 (C3-C8) cycloalkyl group Chemical class 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 239000005877 Alpha-Cypermethrin Substances 0.000 description 5
- 241000193388 Bacillus thuringiensis Species 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 5
- MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 0.000 description 5
- 244000068988 Glycine max Species 0.000 description 5
- 241000257303 Hymenoptera Species 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 235000002595 Solanum tuberosum Nutrition 0.000 description 5
- 244000061456 Solanum tuberosum Species 0.000 description 5
- 240000006394 Sorghum bicolor Species 0.000 description 5
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 229920000180 alkyd Polymers 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 230000003373 anti-fouling effect Effects 0.000 description 5
- 229940097012 bacillus thuringiensis Drugs 0.000 description 5
- 235000005822 corn Nutrition 0.000 description 5
- 230000007123 defense Effects 0.000 description 5
- 229960003887 dichlorophen Drugs 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 235000013399 edible fruits Nutrition 0.000 description 5
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/24—Radicals substituted by oxygen atoms
-
- 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
- A01N43/74—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 five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Health & Medical Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10118310A DE10118310A1 (de) | 2001-04-12 | 2001-04-12 | Hetarylsubstituierte carbocyclische 1,3-Dione |
| UA20031110185A UA76749C2 (uk) | 2001-04-12 | 2002-02-04 | Тіазолілзаміщені карбоциклічні 1,3-діони |
| ES02766566T ES2271332T3 (es) | 2001-04-12 | 2002-04-02 | 1,3-dionas carbociclicas tiazolil-substituidas como agentes pesticidas. |
| US10/474,308 US7595404B2 (en) | 2001-04-12 | 2002-04-02 | Thiazolyl-substituted carbocyclic 1,3-diones as pesticidal agents |
| CA2443642A CA2443642C (en) | 2001-04-12 | 2002-04-02 | Hetaryl-substituted carbocyclic 1,3-diones |
| CNB2006100956330A CN100537551C (zh) | 2001-04-12 | 2002-04-02 | 作为杀虫剂的被噻唑基取代的碳环1,3-二酮类化合物 |
| AT02766566T ATE340787T1 (de) | 2001-04-12 | 2002-04-02 | Thiazolylsubstituierte carbocyclische 1,3-dione als schädlingsbekämpfungsmittel |
| KR1020037013128A KR100862892B1 (ko) | 2001-04-12 | 2002-04-02 | 살해충제로서의 티아졸릴-치환된 카보사이클릭 1,3-디온 |
| CNB028116569A CN1272329C (zh) | 2001-04-12 | 2002-04-02 | 作为杀虫剂的被噻唑基取代的碳环1,3－二酮类化合物 |
| DK02766566T DK1381596T3 (da) | 2001-04-12 | 2002-04-02 | Thiazolylsubstituerede carbocykliske 1,3-dioner som pesticider |
| RU2003133144/04A RU2306310C2 (ru) | 2001-04-12 | 2002-04-02 | Замещенные тиазолилом карбоциклические 1,3-дионы в качестве средств для борьбы с вредителями |
| PL02364391A PL364391A1 (en) | 2001-04-12 | 2002-04-02 | Thiazolyl-substituted carbocyclic 1,3-diones as pesticidal agents |
| BRPI0209082-1A BR0209082B1 (pt) | 2001-04-12 | 2002-04-02 | 1,3-dionas carbocíclicas substituídas com tiazolila, pesticidas, herbicidas e fungicidas compreendendo as mesmas, processos para a preparação dos referidos compostos, para o combate de pragas animais, plantas indesejáveis e fungos e para a produção de pesticidas, herbicidas e fungicidas, bem como o uso dos referidos compostos |
| JP2002585400A JP4413497B2 (ja) | 2001-04-12 | 2002-04-02 | 農薬としてのチアゾリル置換炭素環−１，３−ジオン |
| EP02766566A EP1381596B1 (de) | 2001-04-12 | 2002-04-02 | Thiazolylsubstituierte carbocyclische 1,3-dione als schädlingsbekämpfungsmittel |
| PCT/EP2002/003620 WO2002088098A1 (de) | 2001-04-12 | 2002-04-02 | Thiazolylsubstituierte carbocyclische 1,3-dione als schädlingsbekämpfungsmittel |
| DE50208258T DE50208258D1 (de) | 2001-04-12 | 2002-04-02 | Thiazolylsubstituierte carbocyclische 1,3-dione als schädlingsbekämpfungsmittel |
| MXPA03009315A MXPA03009315A (es) | 2001-04-12 | 2002-04-02 | 1.3-dionas carbociclicas tiazolil-substituidas como agentes pesticidas. |
| ARP020101269A AR035454A1 (es) | 2001-04-12 | 2002-04-05 | 1,3-dionas carbociclicas hetaril-substituidas;, procedimiento para su obtencion; compuestos intermediarios; agentes pesticidas, herbicidas y fungicidas; procedimiento para la lucha contra las pestes animales, contra el crecimiento indeseable de las plantas y contra los hongos; empleo de estos compue |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10118310A DE10118310A1 (de) | 2001-04-12 | 2001-04-12 | Hetarylsubstituierte carbocyclische 1,3-Dione |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10118310A1 true DE10118310A1 (de) | 2002-10-17 |
Family
ID=7681383
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10118310A Withdrawn DE10118310A1 (de) | 2001-04-12 | 2001-04-12 | Hetarylsubstituierte carbocyclische 1,3-Dione |
| DE50208258T Expired - Lifetime DE50208258D1 (de) | 2001-04-12 | 2002-04-02 | Thiazolylsubstituierte carbocyclische 1,3-dione als schädlingsbekämpfungsmittel |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE50208258T Expired - Lifetime DE50208258D1 (de) | 2001-04-12 | 2002-04-02 | Thiazolylsubstituierte carbocyclische 1,3-dione als schädlingsbekämpfungsmittel |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US7595404B2 (enExample) |
| EP (1) | EP1381596B1 (enExample) |
| JP (1) | JP4413497B2 (enExample) |
| KR (1) | KR100862892B1 (enExample) |
| CN (2) | CN1272329C (enExample) |
| AR (1) | AR035454A1 (enExample) |
| AT (1) | ATE340787T1 (enExample) |
| BR (1) | BR0209082B1 (enExample) |
| CA (1) | CA2443642C (enExample) |
| DE (2) | DE10118310A1 (enExample) |
| DK (1) | DK1381596T3 (enExample) |
| ES (1) | ES2271332T3 (enExample) |
| MX (1) | MXPA03009315A (enExample) |
| PL (1) | PL364391A1 (enExample) |
| RU (1) | RU2306310C2 (enExample) |
| UA (1) | UA76749C2 (enExample) |
| WO (1) | WO2002088098A1 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7338969B2 (en) * | 2002-03-08 | 2008-03-04 | Quonova, Llc | Modulation of pathogenicity |
| WO2009030450A2 (en) | 2007-09-03 | 2009-03-12 | Syngenta Limited | Novel herbicides |
| WO2011012862A1 (en) | 2009-07-31 | 2011-02-03 | Syngenta Limited | Herbicidally active heteroaryl-sυbstitυted cyclic diones or derivatives thereof |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10331675A1 (de) * | 2003-07-14 | 2005-02-10 | Bayer Cropscience Ag | Hetarylsubstituierte Pyrazolidindion-Derivate |
| GB0704652D0 (en) * | 2007-03-09 | 2007-04-18 | Syngenta Participations Ag | Novel herbicides |
| GB0712653D0 (en) | 2007-06-28 | 2007-08-08 | Syngenta Ltd | Novel herbicides |
| GB0714981D0 (en) * | 2007-08-01 | 2007-09-12 | Syngenta Ltd | Novel herbicides |
| GB0819205D0 (en) | 2008-10-20 | 2008-11-26 | Syngenta Ltd | Novel herbicides |
| CN103857661B (zh) * | 2011-08-11 | 2016-11-16 | 拜耳知识产权有限责任公司 | 1,2,4‑三唑基取代的酮烯醇 |
| IL310022B2 (en) * | 2021-07-12 | 2024-11-01 | Fortephest Ltd | Novel derivatives of non-coded amino acids and their use as herbicides |
| CN116196314B (zh) * | 2023-05-04 | 2023-08-15 | 广州市妇女儿童医疗中心 | Ri-1或其盐在制备防治胃肠道疾病的药物中的应用 |
| CN116589393A (zh) * | 2023-05-19 | 2023-08-15 | 开封博凯生物化工有限公司 | 以二正丁胺为缚酸剂生产溴虫腈的工艺 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL130759C (enExample) * | 1965-10-07 | |||
| US4659372A (en) * | 1977-03-28 | 1987-04-21 | Union Carbide Corporation | Biocidal 2-aryl-1,3-cyclohexanedione enol ester compounds |
| PT67818A (en) | 1977-03-28 | 1978-04-01 | Union Carbide Corp | Process for the synthesis of biocidal 2-aryl-1,3-cycloalkanedionas and their enol esters |
| CN1003445B (zh) * | 1984-10-03 | 1989-03-01 | 武田药品工业株式会社 | 噻唑烷二酮衍生物，其制备方法和用途 |
| GB8826035D0 (en) | 1988-11-07 | 1988-12-14 | Ici Plc | Herbicidal compositions |
-
2001
- 2001-04-12 DE DE10118310A patent/DE10118310A1/de not_active Withdrawn
-
2002
- 2002-02-04 UA UA20031110185A patent/UA76749C2/uk unknown
- 2002-04-02 JP JP2002585400A patent/JP4413497B2/ja not_active Expired - Fee Related
- 2002-04-02 KR KR1020037013128A patent/KR100862892B1/ko not_active Expired - Fee Related
- 2002-04-02 CN CNB028116569A patent/CN1272329C/zh not_active Expired - Fee Related
- 2002-04-02 BR BRPI0209082-1A patent/BR0209082B1/pt not_active IP Right Cessation
- 2002-04-02 AT AT02766566T patent/ATE340787T1/de not_active IP Right Cessation
- 2002-04-02 ES ES02766566T patent/ES2271332T3/es not_active Expired - Lifetime
- 2002-04-02 PL PL02364391A patent/PL364391A1/xx not_active Application Discontinuation
- 2002-04-02 DE DE50208258T patent/DE50208258D1/de not_active Expired - Lifetime
- 2002-04-02 CN CNB2006100956330A patent/CN100537551C/zh not_active Expired - Fee Related
- 2002-04-02 US US10/474,308 patent/US7595404B2/en not_active Expired - Fee Related
- 2002-04-02 DK DK02766566T patent/DK1381596T3/da active
- 2002-04-02 MX MXPA03009315A patent/MXPA03009315A/es active IP Right Grant
- 2002-04-02 WO PCT/EP2002/003620 patent/WO2002088098A1/de not_active Ceased
- 2002-04-02 CA CA2443642A patent/CA2443642C/en not_active Expired - Fee Related
- 2002-04-02 RU RU2003133144/04A patent/RU2306310C2/ru not_active IP Right Cessation
- 2002-04-02 EP EP02766566A patent/EP1381596B1/de not_active Expired - Lifetime
- 2002-04-05 AR ARP020101269A patent/AR035454A1/es not_active Application Discontinuation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7338969B2 (en) * | 2002-03-08 | 2008-03-04 | Quonova, Llc | Modulation of pathogenicity |
| WO2009030450A2 (en) | 2007-09-03 | 2009-03-12 | Syngenta Limited | Novel herbicides |
| WO2011012862A1 (en) | 2009-07-31 | 2011-02-03 | Syngenta Limited | Herbicidally active heteroaryl-sυbstitυted cyclic diones or derivatives thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2443642A1 (en) | 2002-11-07 |
| UA76749C2 (uk) | 2006-09-15 |
| CN100537551C (zh) | 2009-09-09 |
| CN1880308A (zh) | 2006-12-20 |
| EP1381596B1 (de) | 2006-09-27 |
| CN1272329C (zh) | 2006-08-30 |
| RU2003133144A (ru) | 2005-05-10 |
| ATE340787T1 (de) | 2006-10-15 |
| AR035454A1 (es) | 2004-05-26 |
| RU2306310C2 (ru) | 2007-09-20 |
| PL364391A1 (en) | 2004-12-13 |
| KR100862892B1 (ko) | 2008-10-13 |
| DE50208258D1 (de) | 2006-11-09 |
| ES2271332T3 (es) | 2007-04-16 |
| JP4413497B2 (ja) | 2010-02-10 |
| CA2443642C (en) | 2011-03-08 |
| EP1381596A1 (de) | 2004-01-21 |
| US20070135630A1 (en) | 2007-06-14 |
| MXPA03009315A (es) | 2004-02-12 |
| KR20040067869A (ko) | 2004-07-30 |
| DK1381596T3 (da) | 2007-02-05 |
| WO2002088098A1 (de) | 2002-11-07 |
| BR0209082A (pt) | 2004-08-10 |
| CN1514830A (zh) | 2004-07-21 |
| BR0209082B1 (pt) | 2014-10-07 |
| US7595404B2 (en) | 2009-09-29 |
| JP2004528350A (ja) | 2004-09-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8127 | New person/name/address of the applicant |
Owner name: BAYER CROPSCIENCE AG, 40789 MONHEIM, DE |
|
| 8139 | Disposal/non-payment of the annual fee |