DE2136923A1 - Substituierte benzthiazole, verfahren zu ihrer herstellung und ihre verwendung als fungizide und bakterizide - Google Patents
Substituierte benzthiazole, verfahren zu ihrer herstellung und ihre verwendung als fungizide und bakterizideInfo
- Publication number
- DE2136923A1 DE2136923A1 DE2136923A DE2136923A DE2136923A1 DE 2136923 A1 DE2136923 A1 DE 2136923A1 DE 2136923 A DE2136923 A DE 2136923A DE 2136923 A DE2136923 A DE 2136923A DE 2136923 A1 DE2136923 A1 DE 2136923A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- substituted
- carbon atoms
- active ingredient
- hydrogen
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 9
- 239000000417 fungicide Substances 0.000 title claims description 6
- 239000003899 bactericide agent Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 4
- 239000000460 chlorine Substances 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 12
- 241000233866 Fungi Species 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 241000894006 Bacteria Species 0.000 claims description 8
- LMIAGQODFKONRT-UHFFFAOYSA-N 3-oxido-1,3-benzothiazol-3-ium Chemical class C1=CC=C2[N+]([O-])=CSC2=C1 LMIAGQODFKONRT-UHFFFAOYSA-N 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 230000000855 fungicidal effect Effects 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 239000004606 Fillers/Extenders Substances 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 150000003018 phosphorus compounds Chemical class 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 53
- 238000012360 testing method Methods 0.000 description 18
- 241000196324 Embryophyta Species 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 239000007788 liquid Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 229920001817 Agar Polymers 0.000 description 8
- 206010061217 Infestation Diseases 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000008272 agar Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 241000209140 Triticum Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 239000011877 solvent mixture Substances 0.000 description 5
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 4
- 241000589652 Xanthomonas oryzae Species 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 239000013256 coordination polymer Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 238000011081 inoculation Methods 0.000 description 4
- 235000015097 nutrients Nutrition 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 241000209094 Oryza Species 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000010419 agar Nutrition 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 235000013532 brandy Nutrition 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 235000021186 dishes Nutrition 0.000 description 3
- 231100000162 fungitoxic Toxicity 0.000 description 3
- 230000002464 fungitoxic effect Effects 0.000 description 3
- 239000001963 growth medium Substances 0.000 description 3
- 239000002054 inoculum Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- -1 phenyl radicals Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000004575 stone Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 241000223221 Fusarium oxysporum Species 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 208000012868 Overgrowth Diseases 0.000 description 2
- 241001617088 Thanatephorus sasakii Species 0.000 description 2
- 241000722093 Tilletia caries Species 0.000 description 2
- 241001123669 Verticillium albo-atrum Species 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229920001577 copolymer Chemical class 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 230000035784 germination Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000017066 negative regulation of growth Effects 0.000 description 2
- 238000010899 nucleation Methods 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 241000223600 Alternaria Species 0.000 description 1
- 241000235349 Ascomycota Species 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000228437 Cochliobolus Species 0.000 description 1
- 241000222199 Colletotrichum Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- 241000879841 Fusarium oxysporum f. cubense Species 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 241001459558 Monographella nivalis Species 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- 241000131448 Mycosphaerella Species 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 241000222831 Phialophora <Chaetothyriales> Species 0.000 description 1
- 241001149949 Phytophthora cactorum Species 0.000 description 1
- 241000184297 Pseudocercospora musae Species 0.000 description 1
- 241000228454 Pyrenophora graminea Species 0.000 description 1
- 241000221696 Sclerotinia sclerotiorum Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241000561282 Thielaviopsis basicola Species 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical class ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 238000001720 action spectrum Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000002353 algacidal effect Effects 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 208000024386 fungal infectious disease Diseases 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 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
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000001965 potato dextrose agar Substances 0.000 description 1
- 239000003380 propellant Substances 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
- 235000009566 rice Nutrition 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000004763 spore germination Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical class OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE786520D BE786520A (fr) | 1971-07-23 | Nouveaux benzothiazoles substitues, leur preparation et leur application comme fongicides et bactericides | |
| DE2136923A DE2136923A1 (de) | 1971-07-23 | 1971-07-23 | Substituierte benzthiazole, verfahren zu ihrer herstellung und ihre verwendung als fungizide und bakterizide |
| US00270391A US3852298A (en) | 1971-07-23 | 1972-07-10 | Certain polysubstituted benzothiazoles |
| IL39956A IL39956A (en) | 1971-07-23 | 1972-07-20 | Substituted benzothiazoles,their preparation and fungicidal and bactericidal compositions containing them |
| IT27297/72A IT963262B (it) | 1971-07-23 | 1972-07-21 | Benzotiazoli sostituiti procedimen to per la loro preparazione e loro impiego come fungicidi e batterici di |
| NL7210126A NL7210126A (en) | 1971-07-23 | 1972-07-21 | Substituted benzothiazole derivs - with fungicidal and bactericidal activity |
| GB3421972A GB1363976A (en) | 1971-07-23 | 1972-07-21 | Substituted benzthiazoles process for their preparation and their use as fungicides and bactericides |
| FR7226385A FR2147622A5 (enExample) | 1971-07-23 | 1972-07-21 | |
| CH1095472A CH535253A (de) | 1971-07-23 | 1972-07-21 | Verfahren zur Herstellung von substituierten Benzthiazolen |
| NL7210130A NL7210130A (enExample) | 1971-07-23 | 1972-07-21 | |
| BR4894/72A BR7204894D0 (pt) | 1971-07-23 | 1972-07-21 | Processo para preparacao de benzotiazois substituidos e composicoes fungicidas e bactericidas a base destes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2136923A DE2136923A1 (de) | 1971-07-23 | 1971-07-23 | Substituierte benzthiazole, verfahren zu ihrer herstellung und ihre verwendung als fungizide und bakterizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2136923A1 true DE2136923A1 (de) | 1973-02-01 |
Family
ID=5814644
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2136923A Pending DE2136923A1 (de) | 1971-07-23 | 1971-07-23 | Substituierte benzthiazole, verfahren zu ihrer herstellung und ihre verwendung als fungizide und bakterizide |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3852298A (enExample) |
| BE (1) | BE786520A (enExample) |
| BR (1) | BR7204894D0 (enExample) |
| CH (1) | CH535253A (enExample) |
| DE (1) | DE2136923A1 (enExample) |
| FR (1) | FR2147622A5 (enExample) |
| GB (1) | GB1363976A (enExample) |
| IL (1) | IL39956A (enExample) |
| IT (1) | IT963262B (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0334138A1 (de) * | 1988-03-25 | 1989-09-27 | Bayer Ag | 7-Substituierte 2-Carbonamido-benzthiazol-3-oxide |
| US5183898A (en) * | 1989-04-07 | 1993-02-02 | Bayer Aktiengesellschaft | Pesticidal nitro-substituted benzothiazolones |
| WO2012069743A1 (fr) | 2010-11-22 | 2012-05-31 | Sanofi | Derives de nitrobenzothiazoles et leur utilisation pour le traitment de la tubercolose |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8406906D0 (en) * | 1984-03-16 | 1984-04-18 | Akzo Nv | Benzo-thiazole and benzothiophene derivatives |
| US5504098A (en) * | 1993-02-19 | 1996-04-02 | Asahi Kasei Kogyo Kabushiki Kaisha | Benzothiazolesulfonamide derivative, method for preparing the same, and use thereof |
| CA2117413C (en) * | 1993-07-30 | 2006-11-21 | Neil Geach | Herbicidal isoxazole-4-yl-methanone derivatives |
| US5900426A (en) * | 1995-03-28 | 1999-05-04 | Nippon Zoki Pharmaceutical Co., Ltd. | Benzothiazole derivatives |
| US6297198B1 (en) * | 1996-05-14 | 2001-10-02 | Syngenta Participations Ag | Isoxazole derivatives and their use as herbicides |
| EP0913245A4 (en) * | 1997-02-25 | 2002-07-10 | Kao Corp | CLAMPING DEVICE FOR BLOW MOLDING MACHINES |
| US7377536B2 (en) * | 2006-05-12 | 2008-05-27 | Rehme Mark L | Shock absorbing trailer hitch |
| CN110367264B (zh) * | 2019-08-26 | 2021-11-30 | 浙江工业大学 | 一种取代苯并噻唑c2羟基烷基化衍生物作为杀菌剂的应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1904653A1 (de) * | 1969-01-31 | 1970-08-13 | Bayer Ag | Substituierte Benzthiazol-N-oxide |
-
0
- BE BE786520D patent/BE786520A/xx unknown
-
1971
- 1971-07-23 DE DE2136923A patent/DE2136923A1/de active Pending
-
1972
- 1972-07-10 US US00270391A patent/US3852298A/en not_active Expired - Lifetime
- 1972-07-20 IL IL39956A patent/IL39956A/xx unknown
- 1972-07-21 BR BR4894/72A patent/BR7204894D0/pt unknown
- 1972-07-21 FR FR7226385A patent/FR2147622A5/fr not_active Expired
- 1972-07-21 IT IT27297/72A patent/IT963262B/it active
- 1972-07-21 GB GB3421972A patent/GB1363976A/en not_active Expired
- 1972-07-21 CH CH1095472A patent/CH535253A/de not_active IP Right Cessation
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0334138A1 (de) * | 1988-03-25 | 1989-09-27 | Bayer Ag | 7-Substituierte 2-Carbonamido-benzthiazol-3-oxide |
| US4959379A (en) * | 1988-03-25 | 1990-09-25 | Bayer Aktiengesellschaft | Pesticidal 7-substituted 2-carboxamido-benzothiazole 3-oxides |
| US5183898A (en) * | 1989-04-07 | 1993-02-02 | Bayer Aktiengesellschaft | Pesticidal nitro-substituted benzothiazolones |
| WO2012069743A1 (fr) | 2010-11-22 | 2012-05-31 | Sanofi | Derives de nitrobenzothiazoles et leur utilisation pour le traitment de la tubercolose |
| US8993561B2 (en) | 2010-11-22 | 2015-03-31 | Sanofi | Nitrobenzothiazole derivatives, preparation thereof and therapeutic applications thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| IL39956A0 (en) | 1972-09-28 |
| BR7204894D0 (pt) | 1973-07-10 |
| IT963262B (it) | 1974-01-10 |
| FR2147622A5 (enExample) | 1973-03-09 |
| IL39956A (en) | 1975-03-13 |
| BE786520A (fr) | 1973-01-22 |
| GB1363976A (en) | 1974-08-21 |
| US3852298A (en) | 1974-12-03 |
| CH535253A (de) | 1973-03-31 |
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