DD149304A5 - Schaedlingsbekaempfungsmittel - Google Patents
Schaedlingsbekaempfungsmittel Download PDFInfo
- Publication number
- DD149304A5 DD149304A5 DD80219322A DD21932280A DD149304A5 DD 149304 A5 DD149304 A5 DD 149304A5 DD 80219322 A DD80219322 A DD 80219322A DD 21932280 A DD21932280 A DD 21932280A DD 149304 A5 DD149304 A5 DD 149304A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- compounds
- formula
- optionally substituted
- halogen
- alkyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 37
- -1 metal complex compounds Chemical class 0.000 claims abstract description 11
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- 239000000575 pesticide Substances 0.000 claims abstract description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims abstract description 3
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 3
- 150000007524 organic acids Chemical class 0.000 claims abstract description 3
- 235000005985 organic acids Nutrition 0.000 claims abstract description 3
- 150000003839 salts Chemical class 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- 239000011593 sulfur Substances 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- 150000002118 epoxides Chemical class 0.000 claims abstract 2
- 101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 241000607479 Yersinia pestis Species 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims description 2
- 241000233866 Fungi Species 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 239000000758 substrate Substances 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 abstract description 6
- 238000002360 preparation method Methods 0.000 abstract description 5
- 101100242909 Streptococcus pneumoniae (strain ATCC BAA-255 / R6) pbpA gene Proteins 0.000 abstract 1
- 101100269618 Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4) aliA gene Proteins 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 241000196324 Embryophyta Species 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 13
- 125000001309 chloro group Chemical group Cl* 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 206010061217 Infestation Diseases 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 7
- 241000221785 Erysiphales Species 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 240000008067 Cucumis sativus Species 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 241000209140 Triticum Species 0.000 description 4
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 4
- 238000005660 chlorination reaction Methods 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- ZRDUSMYWDRPZRM-UHFFFAOYSA-N 2-sec-butyl-4,6-dinitrophenyl 3-methylbut-2-enoate Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)C=C(C)C ZRDUSMYWDRPZRM-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241000209219 Hordeum Species 0.000 description 3
- 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 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- TUALNUKMCVJPFZ-UHFFFAOYSA-N methyl 3-chloro-2-(4-chlorophenyl)prop-2-enoate Chemical compound COC(=O)C(=CCl)C1=CC=C(Cl)C=C1 TUALNUKMCVJPFZ-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 2
- YTOPFCCWCSOHFV-UHFFFAOYSA-N 2,6-dimethyl-4-tridecylmorpholine Chemical compound CCCCCCCCCCCCCN1CC(C)OC(C)C1 YTOPFCCWCSOHFV-UHFFFAOYSA-N 0.000 description 2
- 241001480061 Blumeria graminis Species 0.000 description 2
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
- 241000896246 Golovinomyces cichoracearum Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- BWMIENJPXXKETO-UHFFFAOYSA-N methyl 2-(4-chlorophenyl)-3-hydroxyprop-2-enoate Chemical compound COC(=O)C(=CO)C1=CC=C(Cl)C=C1 BWMIENJPXXKETO-UHFFFAOYSA-N 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 231100000208 phytotoxic Toxicity 0.000 description 2
- 230000000885 phytotoxic effect Effects 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- YOBOXHGSEJBUPB-MTOQALJVSA-N (z)-4-hydroxypent-3-en-2-one;zirconium Chemical compound [Zr].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O YOBOXHGSEJBUPB-MTOQALJVSA-N 0.000 description 1
- JLIDRDJNLAWIKT-UHFFFAOYSA-N 1,2-dimethyl-3h-benzo[e]indole Chemical compound C1=CC=CC2=C(C(=C(C)N3)C)C3=CC=C21 JLIDRDJNLAWIKT-UHFFFAOYSA-N 0.000 description 1
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
- UFLFSJVTFSZTKX-UHFFFAOYSA-N 2,2-dimethylmorpholine Chemical compound CC1(C)CNCCO1 UFLFSJVTFSZTKX-UHFFFAOYSA-N 0.000 description 1
- CMJUNAQINNWKAU-KTKRTIGZSA-N 2-[[(z)-2-oxononadec-10-enyl]amino]ethanesulfonic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)CNCCS(O)(=O)=O CMJUNAQINNWKAU-KTKRTIGZSA-N 0.000 description 1
- QZADLIOPLWMBMT-UHFFFAOYSA-N 2-methylpropyl 2-(4-chlorophenyl)-3,3-bis(1,2,4-triazol-1-yl)propanoate Chemical compound C=1C=C(Cl)C=CC=1C(C(=O)OCC(C)C)C(N1N=CN=C1)N1C=NC=N1 QZADLIOPLWMBMT-UHFFFAOYSA-N 0.000 description 1
- YSSXTTHAZYNCIB-UHFFFAOYSA-N 2-methylpropyl 3-chloro-2-(4-chlorophenyl)prop-2-enoate Chemical compound CC(C)COC(=O)C(=CCl)C1=CC=C(Cl)C=C1 YSSXTTHAZYNCIB-UHFFFAOYSA-N 0.000 description 1
- SWECMOXUNJKPPZ-UHFFFAOYSA-N 3-chloro-2-phenylprop-2-enoic acid Chemical compound ClC=C(C(=O)O)C1=CC=CC=C1 SWECMOXUNJKPPZ-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 101710126741 Monodehydroascorbate reductase Proteins 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- DULCUDSUACXJJC-UHFFFAOYSA-N benzeneacetic acid ethyl ester Natural products CCOC(=O)CC1=CC=CC=C1 DULCUDSUACXJJC-UHFFFAOYSA-N 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006013 carbendazim Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000005068 cooling lubricant Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- AAFFTDXPYADISO-UHFFFAOYSA-N cyclohexyne Chemical compound C1CCC#CC1 AAFFTDXPYADISO-UHFFFAOYSA-N 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- GOJFMMKGEBHNMT-UHFFFAOYSA-N ethoxyarsonic acid Chemical compound CCO[As](O)(O)=O GOJFMMKGEBHNMT-UHFFFAOYSA-N 0.000 description 1
- ZQCUSIHDKTWLTA-CSKARUKUSA-N ethyl (e)-3-hydroxy-2-phenylprop-2-enoate Chemical compound CCOC(=O)C(=C\O)\C1=CC=CC=C1 ZQCUSIHDKTWLTA-CSKARUKUSA-N 0.000 description 1
- NZEZNWWSXRYCDV-UHFFFAOYSA-N ethyl 3-chloro-2-phenylprop-2-enoate Chemical compound CCOC(=O)C(=CCl)C1=CC=CC=C1 NZEZNWWSXRYCDV-UHFFFAOYSA-N 0.000 description 1
- ZQCUSIHDKTWLTA-UHFFFAOYSA-N ethyl 3-hydroxy-2-phenylprop-2-enoate Chemical compound CCOC(=O)C(=CO)C1=CC=CC=C1 ZQCUSIHDKTWLTA-UHFFFAOYSA-N 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 244000053095 fungal pathogen Species 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000005555 metalworking Methods 0.000 description 1
- WWIYGBWRUXQDND-UHFFFAOYSA-N methyl 2-(4-chlorophenyl)acetate Chemical compound COC(=O)CC1=CC=C(Cl)C=C1 WWIYGBWRUXQDND-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- ZACLAFCJNHWLDL-UHFFFAOYSA-N n-methylideneformamide Chemical compound C=NC=O ZACLAFCJNHWLDL-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 229920002113 octoxynol Polymers 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- DYGZUKUKAMNWBN-UHFFFAOYSA-N propan-2-yl 2-(4-chlorophenyl)-3,3-bis(1,2,4-triazol-1-yl)propanoate Chemical compound C=1C=C(Cl)C=CC=1C(C(=O)OC(C)C)C(N1N=CN=C1)N1C=NC=N1 DYGZUKUKAMNWBN-UHFFFAOYSA-N 0.000 description 1
- JVMVQIMXJHWIBL-UHFFFAOYSA-N propan-2-yl 3-chloro-2-(4-chlorophenyl)prop-2-enoate Chemical compound CC(C)OC(=O)C(=CCl)C1=CC=C(Cl)C=C1 JVMVQIMXJHWIBL-UHFFFAOYSA-N 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- XOVSRHHCHKUFKM-UHFFFAOYSA-N s-methylthiohydroxylamine Chemical compound CSN XOVSRHHCHKUFKM-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- C07D231/12—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792908324 DE2908324A1 (de) | 1979-03-03 | 1979-03-03 | Triazolsubstituierte hydratopasaeurederivate, verfahren zu ihrer herstellung und ihre verwendung als pflanzenschutzmittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD149304A5 true DD149304A5 (de) | 1981-07-08 |
Family
ID=6064381
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD80219322A DD149304A5 (de) | 1979-03-03 | 1980-02-28 | Schaedlingsbekaempfungsmittel |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP0015498A3 (el) |
| JP (1) | JPS55118472A (el) |
| AU (1) | AU5607280A (el) |
| BR (1) | BR8001203A (el) |
| DD (1) | DD149304A5 (el) |
| DE (1) | DE2908324A1 (el) |
| DK (1) | DK88780A (el) |
| ES (1) | ES488955A1 (el) |
| GR (1) | GR67008B (el) |
| IL (1) | IL59512A0 (el) |
| PT (1) | PT70891A (el) |
| ZA (1) | ZA801166B (el) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PH23251A (en) * | 1985-03-18 | 1989-06-16 | Sds Biotech Corp | Propionate derivative and nonmedical fungicide containing the same |
| DE10231319B4 (de) | 2002-07-11 | 2013-08-14 | Dilo Trading Ag | Verfahren zur Herstellung von Speichern für elektrische Energie auf Basis von wiederaufladbaren Lithium-Polymer-Zellen |
| ES2688815T3 (es) | 2013-05-10 | 2018-11-07 | Karus Therapeutics Limited | Inhibidores de histona desacetilasa novedosos |
| GB201419228D0 (en) * | 2014-10-29 | 2014-12-10 | Karus Therapeutics Ltd | Compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2826760A1 (de) * | 1978-06-19 | 1980-01-03 | Hoechst Ag | Derivate des 1,2,4-triazols |
-
1979
- 1979-03-03 DE DE19792908324 patent/DE2908324A1/de not_active Withdrawn
-
1980
- 1980-02-26 ES ES488955A patent/ES488955A1/es not_active Expired
- 1980-02-27 EP EP80100973A patent/EP0015498A3/de not_active Withdrawn
- 1980-02-28 DD DD80219322A patent/DD149304A5/de unknown
- 1980-02-29 BR BR8001203A patent/BR8001203A/pt unknown
- 1980-02-29 ZA ZA00801166A patent/ZA801166B/xx unknown
- 1980-02-29 GR GR61317A patent/GR67008B/el unknown
- 1980-02-29 JP JP2419080A patent/JPS55118472A/ja active Pending
- 1980-02-29 PT PT70891A patent/PT70891A/pt unknown
- 1980-02-29 DK DK88780A patent/DK88780A/da unknown
- 1980-03-02 IL IL59512A patent/IL59512A0/xx unknown
- 1980-03-03 AU AU56072/80A patent/AU5607280A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP0015498A2 (de) | 1980-09-17 |
| EP0015498A3 (de) | 1980-10-01 |
| ZA801166B (en) | 1981-02-25 |
| DK88780A (da) | 1980-09-04 |
| AU5607280A (en) | 1980-09-04 |
| IL59512A0 (en) | 1980-06-30 |
| PT70891A (en) | 1980-03-01 |
| GR67008B (el) | 1981-05-18 |
| DE2908324A1 (de) | 1980-09-18 |
| ES488955A1 (es) | 1980-09-16 |
| BR8001203A (pt) | 1980-11-04 |
| JPS55118472A (en) | 1980-09-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69217439T2 (de) | Fungizide Silizium enthaltende Verbindungen, deren Herstellung und agrochemische und medizinische Verwendung | |
| DD158845A5 (de) | Pflanzenbehandlungsmittel | |
| DE2735314A1 (de) | Alpha-azolylsulfide und deren derivate | |
| DD144351A5 (de) | Fungizide mittel | |
| EP0019189A1 (de) | Fungizide Mittel, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide | |
| CH635481A5 (de) | Fungizides mittel. | |
| EP0131845A2 (de) | Verwendung von substituierten Diazolyl-alkyl-carbinolen zur Bekämpfung von Pilzen im Pflanzenschutz | |
| DD210834A5 (de) | Biozide zubereitung und ihre verwendung als pflanzenschutzmittel | |
| EP0068144B1 (de) | 1,1-Diphenyl-2-triazolyl-ethane, ihre Herstellung und ihre Verwendung als Fungizide | |
| CH623575A5 (el) | ||
| EP0025882A1 (de) | N-phenylpropylsubstituierte Azole, Verfahren zu ihrer Herstellung und diese enthaltende Fungizide | |
| EP0150036A1 (de) | Azolyl-aryl-alkanol-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DD149453A5 (de) | Schaedlingsbekaempfungsmittel | |
| DE2846980A1 (de) | 1-ethen-azol-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide | |
| EP0057365B1 (de) | Vinylazole, Verfahren zu ihrer Herstellung und ihre Verwendung bei der Bekämpfung von Pilzen | |
| EP0047405A2 (de) | Azolylalkyl-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide | |
| DD149304A5 (de) | Schaedlingsbekaempfungsmittel | |
| EP0029542A2 (de) | Hydroxybutyl-imidazol-Derivate, Verfahren zu ihrer Herstellung, zu letzterer benötigte Zwischenprodukte sowie ihre Verwendung als Fungizide | |
| DE2624529A1 (de) | Aminomethylazol-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide und zur regulierung des pflanzenwachstums | |
| EP0007010A1 (de) | 1,2,4-Triazolderivate, Verfahren zu deren Herstellung, deren Verwendung als Schädlingsbekämpfungsmittel und Pflanzenwuchsregulatoren und diese Derivate enthaltende Schädlingsbekämpfungsmittel | |
| DE3028387A1 (de) | Derivate des 1,2,4-triazols und imidazols, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel | |
| EP0057864A2 (de) | 2-Azolylmethyl-1,3-dioxolan- und -dioxan-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide | |
| CH616664A5 (el) | ||
| EP0142684A2 (de) | Azolyl-tetrahydrofuran-2-yliden-methan-Derivate | |
| EP0102517A2 (de) | Fungizide Mittel |