NO840421L - N-sulfenylerte hydantoiner, en fremgangsmaate til deres fremstilling, og deres anvendelse som mikrobizid - Google Patents

N-sulfenylerte hydantoiner, en fremgangsmaate til deres fremstilling, og deres anvendelse som mikrobizid

Info

Publication number: NO840421L
Authority: NO; Norway
Prior art keywords: alkenyl; hydantoins; cycloalkyl; alkyl; formula
Prior art date: 1983-02-16

Application number

NO840421A

Other languages

English (en)

Norwegian (no)

Inventor

Engelbert Kuehle

Wilfried Paulus

Hermann Genth

Paul Reinecke

Hans-Juergen Rosslenbroich

Original Assignee

Bayer Ag

Priority date (The priority date 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 date listed.)

1983-02-16

Filing date

1984-02-03

Publication date

1984-08-17

1984-02-03 Application filed by Bayer Ag filed Critical Bayer Ag

1984-08-17 Publication of NO840421L publication Critical patent/NO840421L/no

Links

238000000034 method Methods 0.000 title claims description 16
238000002360 preparation method Methods 0.000 title description 5
150000001469 hydantoins Chemical class 0.000 claims abstract description 15
125000003342 alkenyl group Chemical group 0.000 claims abstract description 12
125000000217 alkyl group Chemical group 0.000 claims abstract description 11
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 9
KDRSHFSCTSFYGH-UHFFFAOYSA-N [dichloro(fluoro)methyl] thiohypochlorite Chemical compound FC(Cl)(Cl)SCl KDRSHFSCTSFYGH-UHFFFAOYSA-N 0.000 claims abstract description 8
239000001257 hydrogen Substances 0.000 claims abstract description 5
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 5
239000002855 microbicide agent Substances 0.000 claims abstract description 5
125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 5
239000000463 material Substances 0.000 claims description 17
238000004519 manufacturing process Methods 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 6
239000011230 binding agent Substances 0.000 claims description 6
125000003710 aryl alkyl group Chemical group 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 4
239000003513 alkali Substances 0.000 claims description 3
229910001854 alkali hydroxide Inorganic materials 0.000 claims description 3
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
150000004649 carbonic acid derivatives Chemical class 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 claims description 2
150000001412 amines Chemical class 0.000 claims 1
239000013543 active substance Substances 0.000 abstract description 35
150000001875 compounds Chemical class 0.000 abstract description 8
WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 abstract description 3
229940091173 hydantoin Drugs 0.000 abstract description 3
-1 cycloalkyl radical Chemical class 0.000 description 19
241000196324 Embryophyta Species 0.000 description 14
239000000203 mixture Substances 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
238000009472 formulation Methods 0.000 description 9
239000002904 solvent Substances 0.000 description 9
239000003995 emulsifying agent Substances 0.000 description 8
244000005700 microbiome Species 0.000 description 8
235000015097 nutrients Nutrition 0.000 description 8
239000000243 solution Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000008187 granular material Substances 0.000 description 6
238000005554 pickling Methods 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
239000000969 carrier Substances 0.000 description 5
239000007788 liquid Substances 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
230000001681 protective effect Effects 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
241000233866 Fungi Species 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
235000013312 flour Nutrition 0.000 description 4
150000002430 hydrocarbons Chemical group 0.000 description 4
239000000047 product Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
229920001817 Agar Polymers 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000000853 adhesive Substances 0.000 description 3
230000001070 adhesive effect Effects 0.000 description 3
239000008272 agar Substances 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
230000015556 catabolic process Effects 0.000 description 3
230000008859 change Effects 0.000 description 3
230000006378 damage Effects 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
230000000813 microbial effect Effects 0.000 description 3
239000006072 paste Substances 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
239000002689 soil Substances 0.000 description 3
238000005507 spraying Methods 0.000 description 3
150000003512 tertiary amines Chemical class 0.000 description 3
239000002023 wood Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
240000007594 Oryza sativa Species 0.000 description 2
241000228143 Penicillium Species 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
241000191967 Staphylococcus aureus Species 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
125000002877 alkyl aryl group Chemical group 0.000 description 2
LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
238000001035 drying Methods 0.000 description 2
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000006260 foam Substances 0.000 description 2
239000000417 fungicide Substances 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
238000011081 inoculation Methods 0.000 description 2
239000012948 isocyanate Substances 0.000 description 2
150000002513 isocyanates Chemical class 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
238000002156 mixing Methods 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000011435 rock Substances 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
238000003892 spreading Methods 0.000 description 2
230000007480 spreading Effects 0.000 description 2
239000004575 stone Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
239000000375 suspending agent Substances 0.000 description 2
239000002562 thickening agent Substances 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 1
SVHFBAAZRDCASE-UHFFFAOYSA-N 2-(2-methylphenyl)propan-2-amine Chemical group CC1=CC=CC=C1C(C)(C)N SVHFBAAZRDCASE-UHFFFAOYSA-N 0.000 description 1
125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 description 1
229940061334 2-phenylphenol Drugs 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
IOGVFZXOZMERSG-UHFFFAOYSA-N 3-(2-ethylphenyl)pentan-3-amine Chemical group CCC1=CC=CC=C1C(N)(CC)CC IOGVFZXOZMERSG-UHFFFAOYSA-N 0.000 description 1
ORQMWJLWTGQVFA-UHFFFAOYSA-N 3-cyclohexyl-1-[dichloro(fluoro)methyl]sulfanylimidazolidine-2,4-dione Chemical compound O=C1N(SC(Cl)(Cl)F)CC(=O)N1C1CCCCC1 ORQMWJLWTGQVFA-UHFFFAOYSA-N 0.000 description 1
SLCFSZHXCYYXLK-UHFFFAOYSA-N 3-cyclohexylimidazolidine-2,4-dione Chemical compound O=C1CNC(=O)N1C1CCCCC1 SLCFSZHXCYYXLK-UHFFFAOYSA-N 0.000 description 1
QCVGEOXPDFCNHA-UHFFFAOYSA-N 5,5-dimethyl-2,4-dioxo-1,3-oxazolidine-3-carboxamide Chemical compound CC1(C)OC(=O)N(C(N)=O)C1=O QCVGEOXPDFCNHA-UHFFFAOYSA-N 0.000 description 1
UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
CCIKRLZMGDUEQG-UHFFFAOYSA-N 5-butyl-3-cyclohexylimidazolidine-2,4-dione Chemical compound O=C1C(CCCC)NC(=O)N1C1CCCCC1 CCIKRLZMGDUEQG-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Natural products C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
241000223600 Alternaria Species 0.000 description 1
241000223602 Alternaria alternata Species 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
241000235349 Ascomycota Species 0.000 description 1
241000228212 Aspergillus Species 0.000 description 1
241000228245 Aspergillus niger Species 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
241000223651 Aureobasidium Species 0.000 description 1
241000221198 Basidiomycota Species 0.000 description 1
241001480061 Blumeria graminis Species 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
229910021532 Calcite Inorganic materials 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
241000221955 Chaetomium Species 0.000 description 1
241001515917 Chaetomium globosum Species 0.000 description 1
241000760356 Chytridiomycetes Species 0.000 description 1
244000060011 Cocos nucifera Species 0.000 description 1
235000013162 Cocos nucifera Nutrition 0.000 description 1
241001600093 Coniophora Species 0.000 description 1
241001626940 Coniophora cerebella Species 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
241000195493 Cryptophyta Species 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
102000002322 Egg Proteins Human genes 0.000 description 1
108010000912 Egg Proteins Proteins 0.000 description 1
241000221785 Erysiphales Species 0.000 description 1
241000221787 Erysiphe Species 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
241000223218 Fusarium Species 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
240000005979 Hordeum vulgare Species 0.000 description 1
235000007340 Hordeum vulgare Nutrition 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
241000222418 Lentinus Species 0.000 description 1
241000222451 Lentinus tigrinus Species 0.000 description 1
240000001931 Ludwigia octovalvis Species 0.000 description 1
241001330975 Magnaporthe oryzae Species 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
244000061176 Nicotiana tabacum Species 0.000 description 1
235000002637 Nicotiana tabacum Nutrition 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241000233654 Oomycetes Species 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
241001503460 Plasmodiophorida Species 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
241000222640 Polyporus Species 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
108010009736 Protein Hydrolysates Proteins 0.000 description 1
229920001218 Pullulan Polymers 0.000 description 1
241000231139 Pyricularia Species 0.000 description 1
206010037888 Rash pustular Diseases 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
239000004113 Sepiolite Substances 0.000 description 1
241000191940 Staphylococcus Species 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
241000907561 Sydowia polyspora Species 0.000 description 1
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
241000222355 Trametes versicolor Species 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
241000607479 Yersinia pestis Species 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
230000000895 acaricidal effect Effects 0.000 description 1
239000000642 acaricide Substances 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
HFVAFDPGUJEFBQ-UHFFFAOYSA-M alizarin red S Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=C(S([O-])(=O)=O)C(O)=C2O HFVAFDPGUJEFBQ-UHFFFAOYSA-M 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
235000019270 ammonium chloride Nutrition 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
125000005228 aryl sulfonate group Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
229960000892 attapulgite Drugs 0.000 description 1
244000052616 bacterial pathogen Species 0.000 description 1
239000003899 bactericide agent Substances 0.000 description 1
235000013405 beer Nutrition 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
230000015572 biosynthetic process Effects 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
239000001273 butane Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
239000011111 cardboard Substances 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 1
239000004927 clay Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
238000011109 contamination Methods 0.000 description 1
239000005068 cooling lubricant Substances 0.000 description 1
239000000498 cooling water Substances 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper 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
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
238000001514 detection method Methods 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
125000003963 dichloro group Chemical group Cl* 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
238000007598 dipping method Methods 0.000 description 1
238000009826 distribution Methods 0.000 description 1
239000010459 dolomite Substances 0.000 description 1
229910000514 dolomite Inorganic materials 0.000 description 1
238000010410 dusting Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
235000014103 egg white Nutrition 0.000 description 1
210000000969 egg white Anatomy 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
238000005538 encapsulation Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000003292 glue Substances 0.000 description 1
229960002449 glycine Drugs 0.000 description 1
235000013905 glycine and its sodium salt Nutrition 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000010903 husk Substances 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
230000006872 improvement Effects 0.000 description 1
239000001023 inorganic pigment Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 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
150000002576 ketones Chemical class 0.000 description 1
239000004816 latex Substances 0.000 description 1
229920000126 latex Polymers 0.000 description 1
239000010985 leather Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
239000004579 marble Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
230000003641 microbiacidal effect Effects 0.000 description 1
239000003595 mist Substances 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl 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])[H] 0.000 description 1
239000011368 organic material Substances 0.000 description 1
235000010292 orthophenyl phenol Nutrition 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
239000011087 paperboard Substances 0.000 description 1
235000019319 peptone Nutrition 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000001007 phthalocyanine dye Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
235000011118 potassium hydroxide Nutrition 0.000 description 1
239000001294 propane Substances 0.000 description 1
239000003380 propellant Substances 0.000 description 1
235000019423 pullulan Nutrition 0.000 description 1
239000008262 pumice Substances 0.000 description 1
208000029561 pustule Diseases 0.000 description 1
239000010453 quartz Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
235000019355 sepiolite Nutrition 0.000 description 1
229910052624 sepiolite Inorganic materials 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
239000000779 smoke Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
235000010344 sodium nitrate Nutrition 0.000 description 1
239000004317 sodium nitrate Substances 0.000 description 1
238000007711 solidification Methods 0.000 description 1
230000008023 solidification Effects 0.000 description 1
238000009331 sowing Methods 0.000 description 1
238000009987 spinning Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000004557 technical material Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000004753 textile Substances 0.000 description 1
KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
229960002447 thiram Drugs 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
230000007306 turnover Effects 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- 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
- C07D233/66—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 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 to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/80—Two oxygen atoms, e.g. hydantoin with hetero atoms or acyl radicals directly attached to ring nitrogen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO840421A 1983-02-16 1984-02-03 N-sulfenylerte hydantoiner, en fremgangsmaate til deres fremstilling, og deres anvendelse som mikrobizid NO840421L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19833305203 DE3305203A1 (de)	1983-02-16	1983-02-16	N-sulfenylierte hydantoine, ein verfahren zu ihrer herstellung und ihre verwendung als mikrobizide

Publications (1)

Publication Number	Publication Date
NO840421L true NO840421L (no)	1984-08-17

Family

ID=6190904

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO840421A NO840421L (no)	1983-02-16	1984-02-03	N-sulfenylerte hydantoiner, en fremgangsmaate til deres fremstilling, og deres anvendelse som mikrobizid

Country Status (13)

Country	Link
US (1)	US4547517A (da)
EP (1)	EP0121054B1 (da)
JP (1)	JPS59155369A (da)
AU (1)	AU2428584A (da)
CA (1)	CA1221974A (da)
DE (2)	DE3305203A1 (da)
DK (1)	DK70484A (da)
ES (1)	ES529763A0 (da)
FI (1)	FI840588A (da)
HU (1)	HUT34009A (da)
IE (1)	IE56917B1 (da)
NO (1)	NO840421L (da)
NZ (1)	NZ207124A (da)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4602029A (en) *	1984-10-15	1986-07-22	Chevron Research Company	1-substituted-3-polyhaloalkylthio hydantoin fungicides
FR2706456B1 (fr) *	1993-06-18	1996-06-28	Rhone Poulenc Agrochimie	Dérivés optiquement actifs de 2-imidazoline-5-ones et 2-imidazoline-5-thiones fongicides.
FR2685328B1 (fr) *	1991-12-20	1995-12-01	Rhone Poulenc Agrochimie	Derives de 2-imidazoline-5-ones et 2-imidazoline-5-thiones fongicides.
US6002016A (en) *	1991-12-20	1999-12-14	Rhone-Poulenc Agrochimie	Fungicidal 2-imidazolin-5-ones and 2-imidazoline-5-thiones
US6008370A (en) *	1992-11-25	1999-12-28	Rhone-Poulenc Agrochimie	Fungicidal-2-alkoxy/haloalkoxy-1-(mono- or disubstituted)amino-4,4-disubstituted-2-imidazolin-5-ones
US6514458B1 (en) *	2000-02-25	2003-02-04	Ge Betz, Inc.	Method for removing microbes from surfaces

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL292187A (da) *	1962-05-02
IL45459A (en) *	1973-09-03	1978-01-31	Ciba Geigy Ag	1-(dichlorofluoromethylthio)-3-phenyl-imidazolidine-2,4-dione derivatives their preparation and their use as bactericides and fungicides
DE3222523A1 (de) *	1982-06-16	1983-12-22	Bayer Ag, 5090 Leverkusen	N-sulfenylierte hydantoine

1983
- 1983-02-16 DE DE19833305203 patent/DE3305203A1/de not_active Withdrawn
1984
- 1984-02-03 NO NO840421A patent/NO840421L/no unknown
- 1984-02-07 DE DE8484101202T patent/DE3461532D1/de not_active Expired
- 1984-02-07 EP EP84101202A patent/EP0121054B1/de not_active Expired
- 1984-02-08 AU AU24285/84A patent/AU2428584A/en not_active Withdrawn
- 1984-02-13 JP JP59023064A patent/JPS59155369A/ja active Pending
- 1984-02-13 NZ NZ207124A patent/NZ207124A/en unknown
- 1984-02-13 US US06/579,844 patent/US4547517A/en not_active Expired - Fee Related
- 1984-02-14 FI FI840588A patent/FI840588A/fi not_active Application Discontinuation
- 1984-02-14 CA CA000447337A patent/CA1221974A/en not_active Expired
- 1984-02-15 DK DK70484A patent/DK70484A/da not_active Application Discontinuation
- 1984-02-15 IE IE342/84A patent/IE56917B1/xx unknown
- 1984-02-15 HU HU84596A patent/HUT34009A/hu unknown
- 1984-02-15 ES ES529763A patent/ES529763A0/es active Granted

Also Published As

Publication number	Publication date
ES8500908A1 (es)	1984-11-01
CA1221974A (en)	1987-05-19
FI840588A (fi)	1984-08-17
JPS59155369A (ja)	1984-09-04
FI840588A0 (fi)	1984-02-14
DK70484D0 (da)	1984-02-15
ES529763A0 (es)	1984-11-01
EP0121054B1 (de)	1986-12-03
DK70484A (da)	1984-08-17
DE3461532D1 (en)	1987-01-15
EP0121054A1 (de)	1984-10-10
HUT34009A (en)	1985-01-28
US4547517A (en)	1985-10-15
NZ207124A (en)	1986-05-09
IE56917B1 (en)	1992-01-29
DE3305203A1 (de)	1984-08-16
AU2428584A (en)	1984-08-23
IE840342L (en)	1984-08-16

Publication	Publication Date	Title
NZ212119A (en)	1987-08-31	1-heteroaryl-4-aryl-pyrazolin-5-ones and microbicidal compositions
US3839575A (en)	1974-10-01	2-(pyrazolyl-(1))-benzimidazole fungicidal,and bactericidal agents
NO840421L (no)	1984-08-17	N-sulfenylerte hydantoiner, en fremgangsmaate til deres fremstilling, og deres anvendelse som mikrobizid
US4521412A (en)	1985-06-04	Pesticidal iodopropargylammonium salts
NO752113L (da)	1975-12-30
JP2963243B2 (ja)	1999-10-18	ハロゲノアルキル−アゾリル誘導体類
NO124257B (da)	1972-03-27
JPS635081A (ja)	1988-01-11	Ｎ−スルフエニル化された２−トリフルオロメチル−ベンズイミダゾ−ル
US3869503A (en)	1975-03-04	Substituted amidophenylguanidines
US3766243A (en)	1973-10-16	Ureidophenylisothioureas
US5118702A (en)	1992-06-02	Fungicidal and microbicidal substituted 1-aminomethyl-3-aryl-4-cyano-pyrroles
US3832466A (en)	1974-08-27	3-azolylpropyne fungicidal agents
US3720682A (en)	1973-03-13	Substituted amidophenylthioureas
CA1192912A (en)	1985-09-03	N-sulphenylated benzylsulphonamides, a process and their use as microbicides
US4513003A (en)	1985-04-23	Process for protecting wood using N-(dichlorofluoromethylthio)-3,6-endomethylene-Δ4 -tetrahydrophthalimide
NO822859L (no)	1983-02-25	1-(trihalogenmetyl-sulfenyl)-4-aryl-1,2,4-triazolin-5-on-derivater og fungicider inneholdende disse
US4496575A (en)	1985-01-29	Fungicidal N-sulphenylated hydantoins
US3881018A (en)	1975-04-29	Substituted amidophenylguanidine fungicides
JPS6219575A (ja)	1987-01-28	ベンゾイル−トリアゾリル−酢酸−または−チオ酢酸誘導体、それらの製造方法およびこれらを含有する殺微生物剤
CA1203812A (en)	1986-04-29	Sulfone and process for its preparation
DK165242B (da)	1992-10-26	N-sulfenylerede urinstoffer, fremgangsmaade til deres fremstilling, mikrobicide midler indeholdende dem og disses anvendelse
PT91259B (pt)	1995-05-04	Processo para a preparacao de composicoes microbicidas, contendo derivados de halogeno-vinil-azol
EP0161480B1 (de)	1987-06-03	N-Jodpropargyl-chlormethansulfonamide
JPS591449A (ja)	1984-01-06	ジアミン誘導体、その製造法及び該化合物を有効物質として含有する殺菌剤並びに除黴剤
CA1119605A (en)	1982-03-09	L,3-bis-(trihalomethylsulfenyl)-imidazoline-2,4- diones