DE2025412A1 - Amidophenylisothiohamstoffe, Verfahren zu ihrer Herstellung und ihre fungizide Verwendung - Google Patents
Amidophenylisothiohamstoffe, Verfahren zu ihrer Herstellung und ihre fungizide VerwendungInfo
- Publication number
- DE2025412A1 DE2025412A1 DE19702025412 DE2025412A DE2025412A1 DE 2025412 A1 DE2025412 A1 DE 2025412A1 DE 19702025412 DE19702025412 DE 19702025412 DE 2025412 A DE2025412 A DE 2025412A DE 2025412 A1 DE2025412 A1 DE 2025412A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- alkyl
- halogen
- active ingredient
- amidophenylisothioureas
- 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 10
- 238000002360 preparation method Methods 0.000 title claims description 8
- 230000000855 fungicidal effect Effects 0.000 title description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 241000233866 Fungi Species 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 229940100198 alkylating agent Drugs 0.000 claims description 6
- 239000002168 alkylating agent Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 239000000417 fungicide Substances 0.000 claims description 4
- 239000004606 Fillers/Extenders Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 150000002431 hydrogen 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
- 150000008051 alkyl sulfates Chemical class 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000005228 aryl sulfonate group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 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
- 125000005843 halogen group Chemical group 0.000 claims 3
- 239000004480 active ingredient Substances 0.000 description 52
- 241000196324 Embryophyta Species 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 206010061217 Infestation Diseases 0.000 description 17
- 239000000203 mixture Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 13
- -1 heterocyclic radical Chemical class 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- 239000007788 liquid Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 241000220225 Malus Species 0.000 description 8
- 239000000758 substrate Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 238000011081 inoculation Methods 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 229920001817 Agar Polymers 0.000 description 5
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 239000008272 agar Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 241000209140 Triticum Species 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000221785 Erysiphales Species 0.000 description 3
- 241000489964 Fusicladium Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 241001617088 Thanatephorus sasakii Species 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000002464 fungitoxic effect Effects 0.000 description 3
- 239000002054 inoculum Substances 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 230000009885 systemic effect Effects 0.000 description 3
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 208000012868 Overgrowth Diseases 0.000 description 2
- 241000896242 Podosphaera Species 0.000 description 2
- 241001337928 Podosphaera leucotricha Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 206010039509 Scab Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000000895 acaricidal effect Effects 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 235000013532 brandy Nutrition 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 235000021186 dishes Nutrition 0.000 description 2
- 239000012990 dithiocarbamate Substances 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 231100000162 fungitoxic Toxicity 0.000 description 2
- 230000035784 germination Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 238000005554 pickling Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 239000011435 rock Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000004575 stone Substances 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical class NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 241000223600 Alternaria Species 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000228437 Cochliobolus Species 0.000 description 1
- 241001480059 Erysiphaceae Species 0.000 description 1
- 241000221787 Erysiphe Species 0.000 description 1
- 241000510928 Erysiphe necator Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000896246 Golovinomyces cichoracearum Species 0.000 description 1
- 241001465754 Metazoa 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
- 241001329956 Nothopassalora personata Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000896238 Oidium Species 0.000 description 1
- 241000222831 Phialophora <Chaetothyriales> Species 0.000 description 1
- 241000317981 Podosphaera fuliginea Species 0.000 description 1
- 241000184297 Pseudocercospora musae Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 description 1
- 241000579741 Sphaerotheca <fungi> Species 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 241000722093 Tilletia caries Species 0.000 description 1
- 241000510929 Uncinula Species 0.000 description 1
- 241001123669 Verticillium albo-atrum Species 0.000 description 1
- 241000589652 Xanthomonas oryzae Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 208000024386 fungal infectious disease Diseases 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
- 150000002541 isothioureas Chemical class 0.000 description 1
- 238000009940 knitting Methods 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 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
- 239000008164 mustard oil Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000001965 potato dextrose agar Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/30—Isothioureas
- C07C335/38—Isothioureas containing any of the groups, X being a hetero atom, Y being any atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Feedback Control In General (AREA)
Priority Applications (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702025412 DE2025412A1 (de) | 1970-05-25 | 1970-05-25 | Amidophenylisothiohamstoffe, Verfahren zu ihrer Herstellung und ihre fungizide Verwendung |
| IL36713A IL36713A (en) | 1970-05-25 | 1971-04-26 | Amidophenylisothioureas,their preparation and their use as fungicides |
| CH610371A CH552577A (de) | 1970-05-25 | 1971-04-26 | Verfahren zur herstellung neuer amidophenylisothioharnstoffe und ihre verwendung als aktive komponente zur herstellung fungizider mittel. |
| ZA712801A ZA712801B (en) | 1970-05-25 | 1971-04-30 | Amidophenylisothioureas a process for their preparation and their use as fungicides |
| GB1371671*[A GB1308101A (en) | 1970-05-25 | 1971-05-07 | Amidophenylisothioureas a process for their preparation and their use as fungicides |
| US00141978A US3843715A (en) | 1970-05-25 | 1971-05-10 | Amidophenylisothioureas |
| BG017561A BG17767A3 (bg) | 1970-05-25 | 1971-05-15 | Фунгицидно средство |
| SU1661337A SU373915A1 (ru) | 1971-05-21 | Фунгицид | |
| ES391491A ES391491A1 (es) | 1970-05-25 | 1971-05-24 | Procedimiento para la obtencion de amidofenilisotioureas. |
| NL7107083A NL7107083A (enExample) | 1970-05-25 | 1971-05-24 | |
| SE06665/71A SE363316B (enExample) | 1970-05-25 | 1971-05-24 | |
| DK250971AA DK128073B (da) | 1970-05-25 | 1971-05-24 | Fungicidt virksomme amidophenylisothiourinstoffer. |
| FR7118934A FR2093726A5 (enExample) | 1970-05-25 | 1971-05-25 | |
| BE767645A BE767645A (fr) | 1970-05-25 | 1971-05-25 | Nouvelles amidophenylisothiourees, leur procede de preparation et leur utilisation comme fongicides |
| HUBA2588A HU162535B (enExample) | 1970-05-25 | 1971-05-25 | |
| AT450271A AT304940B (de) | 1970-05-25 | 1971-05-25 | Fungizides Mittel |
| US00360484A US3852463A (en) | 1970-05-25 | 1973-05-15 | Combating fungi with amidophenylisothioureas |
| MY472/73A MY7300472A (en) | 1970-05-25 | 1973-12-30 | Amidophenylisothioureas, a process for their preparation and their use as fungicides |
| CU34532A CU34532A (es) | 1970-05-25 | 1976-06-08 | Diseno de un selector de senales neumáticas de búsqueda directa y/o secuencial |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702025412 DE2025412A1 (de) | 1970-05-25 | 1970-05-25 | Amidophenylisothiohamstoffe, Verfahren zu ihrer Herstellung und ihre fungizide Verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2025412A1 true DE2025412A1 (de) | 1971-12-02 |
Family
ID=5772009
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702025412 Pending DE2025412A1 (de) | 1970-05-25 | 1970-05-25 | Amidophenylisothiohamstoffe, Verfahren zu ihrer Herstellung und ihre fungizide Verwendung |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3843715A (enExample) |
| AT (1) | AT304940B (enExample) |
| BE (1) | BE767645A (enExample) |
| BG (1) | BG17767A3 (enExample) |
| CH (1) | CH552577A (enExample) |
| CU (1) | CU34532A (enExample) |
| DE (1) | DE2025412A1 (enExample) |
| DK (1) | DK128073B (enExample) |
| ES (1) | ES391491A1 (enExample) |
| FR (1) | FR2093726A5 (enExample) |
| GB (1) | GB1308101A (enExample) |
| HU (1) | HU162535B (enExample) |
| IL (1) | IL36713A (enExample) |
| MY (1) | MY7300472A (enExample) |
| NL (1) | NL7107083A (enExample) |
| SE (1) | SE363316B (enExample) |
| ZA (1) | ZA712801B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4001297A (en) * | 1968-06-18 | 1977-01-04 | Nippon Soda Company Limited | Thioureidobenzene preparations and uses thereof |
| US4024236A (en) * | 1972-10-27 | 1977-05-17 | Bayer Aktiengesellschaft | Anthelmintic compositions and uses employing amidophenylisothioureas |
| DE2303048A1 (de) * | 1973-01-23 | 1974-07-25 | Bayer Ag | Benzoylphenylisothioharnstoffe, ein verfahren zu ihrer herstellung, sowie ihre verwendung als arzneimittel |
| DE2434183C2 (de) * | 1974-07-16 | 1982-07-01 | Bayer Ag, 5090 Leverkusen | Substituierte Phenylisothioharnstoffe, ein Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel |
| GB1479624A (en) * | 1974-11-05 | 1977-07-13 | May & Baker Ltd | (3-alkoxycarbonyl-2-thioureido)benzene derivatives |
| GB1602009A (en) * | 1977-08-23 | 1981-11-04 | Rohm & Haas | Isothiourea derivatives |
-
1970
- 1970-05-25 DE DE19702025412 patent/DE2025412A1/de active Pending
-
1971
- 1971-04-26 CH CH610371A patent/CH552577A/xx not_active IP Right Cessation
- 1971-04-26 IL IL36713A patent/IL36713A/xx unknown
- 1971-04-30 ZA ZA712801A patent/ZA712801B/xx unknown
- 1971-05-07 GB GB1371671*[A patent/GB1308101A/en not_active Expired
- 1971-05-10 US US00141978A patent/US3843715A/en not_active Expired - Lifetime
- 1971-05-15 BG BG017561A patent/BG17767A3/xx unknown
- 1971-05-24 DK DK250971AA patent/DK128073B/da unknown
- 1971-05-24 ES ES391491A patent/ES391491A1/es not_active Expired
- 1971-05-24 NL NL7107083A patent/NL7107083A/xx unknown
- 1971-05-24 SE SE06665/71A patent/SE363316B/xx unknown
- 1971-05-25 BE BE767645A patent/BE767645A/xx unknown
- 1971-05-25 AT AT450271A patent/AT304940B/de not_active IP Right Cessation
- 1971-05-25 FR FR7118934A patent/FR2093726A5/fr not_active Expired
- 1971-05-25 HU HUBA2588A patent/HU162535B/hu unknown
-
1973
- 1973-12-30 MY MY472/73A patent/MY7300472A/xx unknown
-
1976
- 1976-06-08 CU CU34532A patent/CU34532A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE767645A (fr) | 1971-11-25 |
| ES391491A1 (es) | 1973-06-16 |
| SE363316B (enExample) | 1974-01-14 |
| CH552577A (de) | 1974-08-15 |
| US3843715A (en) | 1974-10-22 |
| CU34532A (es) | 1981-01-10 |
| GB1308101A (en) | 1973-02-21 |
| BG17767A3 (bg) | 1973-12-25 |
| HU162535B (enExample) | 1973-03-28 |
| MY7300472A (en) | 1973-12-31 |
| ZA712801B (en) | 1972-06-28 |
| DK128073B (da) | 1974-02-25 |
| AT304940B (de) | 1973-01-25 |
| SU373915A3 (enExample) | 1973-03-12 |
| IL36713A (en) | 1974-03-14 |
| IL36713A0 (en) | 1971-06-23 |
| FR2093726A5 (enExample) | 1972-01-28 |
| NL7107083A (enExample) | 1971-11-29 |
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