CA1180334A - N-sulphenylated biurets, processes for their preparation and their use as fungicides - Google Patents
N-sulphenylated biurets, processes for their preparation and their use as fungicidesInfo
- Publication number
- CA1180334A CA1180334A CA000393325A CA393325A CA1180334A CA 1180334 A CA1180334 A CA 1180334A CA 000393325 A CA000393325 A CA 000393325A CA 393325 A CA393325 A CA 393325A CA 1180334 A CA1180334 A CA 1180334A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- carbon atoms
- cyclohexyl
- biuret
- radical
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 19
- 238000002360 preparation method Methods 0.000 title description 6
- 239000000417 fungicide Substances 0.000 title description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 61
- -1 aliphatic radical Chemical class 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 239000003085 diluting agent Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- 239000012948 isocyanate Substances 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 241000233866 Fungi Species 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 4
- 239000002689 soil Substances 0.000 claims description 4
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 4
- AVWRKZWQTYIKIY-UHFFFAOYSA-N ureidocarboxylic acid Natural products NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- BGYWXFPHLHSORG-UHFFFAOYSA-N 1-cyclohexyl-3-(dichloromethylsulfanyl)-3-(ethylcarbamoyl)-1-fluorourea Chemical compound CCNC(=O)N(SC(Cl)Cl)C(=O)N(F)C1CCCCC1 BGYWXFPHLHSORG-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
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000002425 furfuryl group Chemical group C(C1=CC=CO1)* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- JNZUPYJNKZLXOW-UHFFFAOYSA-N 1-(cyclohexylcarbamoyl)-1-(dichloromethylsulfanyl)-3-fluoro-3-propan-2-ylurea Chemical compound CC(C)N(F)C(=O)N(SC(Cl)Cl)C(=O)NC1CCCCC1 JNZUPYJNKZLXOW-UHFFFAOYSA-N 0.000 claims 1
- ZRLYQMBQIJMKPA-UHFFFAOYSA-N 1-(tert-butylcarbamoyl)-3-cyclohexyl-1-(dichloromethylsulfanyl)-3-fluorourea Chemical compound CC(C)(C)NC(=O)N(SC(Cl)Cl)C(=O)N(F)C1CCCCC1 ZRLYQMBQIJMKPA-UHFFFAOYSA-N 0.000 claims 1
- KQHCQWOGYXZRGM-UHFFFAOYSA-N 1-cyclohexyl-3-(dichloromethylsulfanyl)-1-fluoro-3-(methylcarbamoyl)urea Chemical compound CNC(=O)N(SC(Cl)Cl)C(=O)N(F)C1CCCCC1 KQHCQWOGYXZRGM-UHFFFAOYSA-N 0.000 claims 1
- OFEKYZAHAUSXEQ-UHFFFAOYSA-N 1-cyclohexyl-3-(dichloromethylsulfanyl)-1-fluoro-3-(propan-2-ylcarbamoyl)urea Chemical compound CC(C)NC(=O)N(SC(Cl)Cl)C(=O)N(F)C1CCCCC1 OFEKYZAHAUSXEQ-UHFFFAOYSA-N 0.000 claims 1
- IPEWNTLWCRYSRY-UHFFFAOYSA-N [CH2]C1=CC=CO1 Chemical compound [CH2]C1=CC=CO1 IPEWNTLWCRYSRY-UHFFFAOYSA-N 0.000 claims 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims 1
- 230000000855 fungicidal effect Effects 0.000 abstract description 5
- 125000001931 aliphatic group Chemical group 0.000 abstract description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 238000009472 formulation Methods 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 241000209094 Oryza Species 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- BAPZCSMFCUVUHW-UHFFFAOYSA-N dichloro(fluoro)methane Chemical compound F[C](Cl)Cl BAPZCSMFCUVUHW-UHFFFAOYSA-N 0.000 description 6
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- 239000000243 solution Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N Methyl ethyl ketone Natural products CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- 235000007164 Oryza sativa Nutrition 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 125000002877 alkyl aryl group Chemical group 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 241001465180 Botrytis Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
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- 239000002270 dispersing agent Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
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- 230000001681 protective effect Effects 0.000 description 3
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- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
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- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 241001617088 Thanatephorus sasakii Species 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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- FSZKLYCUEQGCKW-UHFFFAOYSA-N phenyl n-(oxomethylidene)carbamate Chemical compound O=C=NC(=O)OC1=CC=CC=C1 FSZKLYCUEQGCKW-UHFFFAOYSA-N 0.000 description 2
- 239000011814 protection agent Substances 0.000 description 2
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- PZRWVFLJNZRVMN-UHFFFAOYSA-N 1-[dichloro(fluoro)methyl]sulfanyl-1-methyl-3-(oxomethylidene)urea Chemical compound FC(Cl)(Cl)SN(C)C(=O)N=C=O PZRWVFLJNZRVMN-UHFFFAOYSA-N 0.000 description 1
- UPTVJAJPBGIRLZ-UHFFFAOYSA-N 2-(trichloromethylsulfanyl)-3a,4,5,7a-tetrahydroisoindole-1,3-dione Chemical compound C1CC=CC2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C21 UPTVJAJPBGIRLZ-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
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- 239000001023 inorganic pigment Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- DCYOBGZUOMKFPA-UHFFFAOYSA-N iron(2+);iron(3+);octadecacyanide Chemical compound [Fe+2].[Fe+2].[Fe+2].[Fe+3].[Fe+3].[Fe+3].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] DCYOBGZUOMKFPA-UHFFFAOYSA-N 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- 235000009973 maize 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
- 235000012054 meals Nutrition 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
- 244000005700 microbiome Species 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 238000002156 mixing Methods 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
- VBBUFMFZDHLELS-UHFFFAOYSA-N n-(oxomethylidene)carbamoyl chloride Chemical compound ClC(=O)N=C=O VBBUFMFZDHLELS-UHFFFAOYSA-N 0.000 description 1
- AKOCAGHYQFWHMQ-UHFFFAOYSA-N n-(trifluoromethylsulfanyl)methanamine Chemical compound CNSC(F)(F)F AKOCAGHYQFWHMQ-UHFFFAOYSA-N 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
- 229920005615 natural polymer Polymers 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
- 239000011368 organic material Substances 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 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
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 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
- 239000007858 starting material Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical compound NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 description 1
- 238000009369 viticulture Methods 0.000 description 1
- 239000002699 waste material Substances 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C313/08—Sulfenic acids; Derivatives thereof
- C07C313/18—Sulfenamides
- C07C313/26—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C313/30—Y being a hetero atom
- C07C313/34—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfenylureas
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/22—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to two ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803049439 DE3049439A1 (de) | 1980-12-30 | 1980-12-30 | N-sulfenylierte biurete, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| DEP3049439.4 | 1980-12-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1180334A true CA1180334A (en) | 1985-01-02 |
Family
ID=6120513
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000393325A Expired CA1180334A (en) | 1980-12-30 | 1981-12-29 | N-sulphenylated biurets, processes for their preparation and their use as fungicides |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4382956A (en, 2012) |
| EP (1) | EP0055442B1 (en, 2012) |
| JP (1) | JPS57136562A (en, 2012) |
| AT (1) | ATE8836T1 (en, 2012) |
| AU (1) | AU526962B2 (en, 2012) |
| BR (1) | BR8108487A (en, 2012) |
| CA (1) | CA1180334A (en, 2012) |
| CS (1) | CS235523B2 (en, 2012) |
| DD (1) | DD201969A5 (en, 2012) |
| DE (2) | DE3049439A1 (en, 2012) |
| DK (1) | DK581581A (en, 2012) |
| ES (1) | ES508408A0 (en, 2012) |
| GR (1) | GR75155B (en, 2012) |
| HU (1) | HU188735B (en, 2012) |
| IL (1) | IL64666A0 (en, 2012) |
| PH (1) | PH17372A (en, 2012) |
| PL (1) | PL128411B1 (en, 2012) |
| PT (1) | PT74160B (en, 2012) |
| ZA (1) | ZA818998B (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3032327A1 (de) * | 1980-08-27 | 1982-04-01 | Bayer Ag, 5090 Leverkusen | N-sulfenylierte harnstoffe, verfahren zu ihrer herstellung, diese enthaltende fungizide mittel und ihre verwendung |
| US4666911A (en) * | 1981-07-14 | 1987-05-19 | Taiho Pharmaceutical Company Limited | Allophanoylpiperazine compound and analgesic composition containing same as active ingredient |
| US4448959A (en) * | 1981-10-19 | 1984-05-15 | Ciba-Geigy Corporation | Chlorosulfonyl urea triazines |
| DE3146231A1 (de) * | 1981-11-21 | 1983-05-26 | Bayer Ag, 5090 Leverkusen | N-sulfenylierte biuret-n"-carbonsaeureester, ein verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
| JP6396203B2 (ja) | 2014-12-25 | 2018-09-26 | 東芝機械株式会社 | 型締装置及び成形装置 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE549534A (en, 2012) | 1955-07-15 | |||
| FR1472975A (fr) * | 1965-09-02 | 1967-03-17 | Azote Office Nat Ind | Dérivés organomercuriques de l'acide isocyanurique |
-
1980
- 1980-12-30 DE DE19803049439 patent/DE3049439A1/de not_active Withdrawn
-
1981
- 1981-12-15 US US06/331,098 patent/US4382956A/en not_active Expired - Fee Related
- 1981-12-16 AU AU78551/81A patent/AU526962B2/en not_active Ceased
- 1981-12-18 DD DD81235964A patent/DD201969A5/de unknown
- 1981-12-19 AT AT81110627T patent/ATE8836T1/de not_active IP Right Cessation
- 1981-12-19 DE DE8181110627T patent/DE3165454D1/de not_active Expired
- 1981-12-19 EP EP81110627A patent/EP0055442B1/de not_active Expired
- 1981-12-21 PT PT74160A patent/PT74160B/pt unknown
- 1981-12-22 CS CS819670A patent/CS235523B2/cs unknown
- 1981-12-25 JP JP56209472A patent/JPS57136562A/ja active Pending
- 1981-12-28 PL PL1981234480A patent/PL128411B1/pl unknown
- 1981-12-28 IL IL64666A patent/IL64666A0/xx unknown
- 1981-12-29 BR BR8108487A patent/BR8108487A/pt unknown
- 1981-12-29 HU HU813983A patent/HU188735B/hu unknown
- 1981-12-29 ZA ZA818998A patent/ZA818998B/xx unknown
- 1981-12-29 ES ES508408A patent/ES508408A0/es active Granted
- 1981-12-29 CA CA000393325A patent/CA1180334A/en not_active Expired
- 1981-12-29 PH PH26689A patent/PH17372A/en unknown
- 1981-12-29 DK DK581581A patent/DK581581A/da not_active Application Discontinuation
-
1982
- 1982-03-04 GR GR66903A patent/GR75155B/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES8300694A1 (es) | 1982-11-01 |
| DK581581A (da) | 1982-07-01 |
| ES508408A0 (es) | 1982-11-01 |
| EP0055442A3 (en) | 1982-08-04 |
| CS235523B2 (en) | 1985-05-15 |
| GR75155B (en, 2012) | 1984-07-13 |
| IL64666A0 (en) | 1982-03-31 |
| US4382956A (en) | 1983-05-10 |
| PT74160B (en) | 1983-05-17 |
| BR8108487A (pt) | 1982-10-19 |
| AU526962B2 (en) | 1983-02-10 |
| AU7855181A (en) | 1982-07-08 |
| HU188735B (en) | 1986-05-28 |
| DE3165454D1 (en) | 1984-09-13 |
| ZA818998B (en) | 1982-12-29 |
| PL128411B1 (en) | 1984-01-31 |
| EP0055442A2 (de) | 1982-07-07 |
| PT74160A (en) | 1982-01-01 |
| JPS57136562A (en) | 1982-08-23 |
| PL234480A1 (en, 2012) | 1982-09-13 |
| ATE8836T1 (de) | 1984-08-15 |
| DD201969A5 (de) | 1983-08-24 |
| EP0055442B1 (de) | 1984-08-08 |
| PH17372A (en) | 1984-08-06 |
| DE3049439A1 (de) | 1982-07-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |