CS243472B2 - Fungicide and method of its efficient substance's production - Google Patents
Fungicide and method of its efficient substance's production Download PDFInfo
- Publication number
- CS243472B2 CS243472B2 CS822699A CS269982A CS243472B2 CS 243472 B2 CS243472 B2 CS 243472B2 CS 822699 A CS822699 A CS 822699A CS 269982 A CS269982 A CS 269982A CS 243472 B2 CS243472 B2 CS 243472B2
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- Czechoslovakia
- Prior art keywords
- group
- carbon atoms
- alkyl
- carbon
- formula
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- 230000000855 fungicidal effect Effects 0.000 title claims description 105
- 238000000034 method Methods 0.000 title claims description 24
- 239000000417 fungicide Substances 0.000 title abstract description 93
- 239000000126 substance Substances 0.000 title description 10
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 cyclic imide Chemical class 0.000 claims abstract description 114
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical class OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims description 131
- 239000000203 mixture Substances 0.000 claims description 66
- 125000004432 carbon atom Chemical group C* 0.000 claims description 62
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 239000013543 active substance Substances 0.000 claims description 31
- 238000002360 preparation method Methods 0.000 claims description 28
- 229910052799 carbon Inorganic materials 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 239000004480 active ingredient Substances 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 23
- 125000000304 alkynyl group Chemical group 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 150000001721 carbon Chemical group 0.000 claims description 4
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 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
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 2
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 241001611408 Nebo Species 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000003610 charcoal Substances 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 230000002140 halogenating effect Effects 0.000 claims 1
- 241000233866 Fungi Species 0.000 abstract description 20
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 abstract description 3
- 241000894007 species Species 0.000 description 81
- 230000002265 prevention Effects 0.000 description 47
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 34
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 32
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 26
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- 230000000694 effects Effects 0.000 description 21
- 239000000843 powder Substances 0.000 description 20
- 230000003449 preventive effect Effects 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- 201000010099 disease Diseases 0.000 description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- 239000000460 chlorine Substances 0.000 description 16
- 229910052801 chlorine Inorganic materials 0.000 description 15
- 239000002689 soil Substances 0.000 description 14
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 13
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 13
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- 239000011575 calcium Substances 0.000 description 11
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- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 10
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 239000004495 emulsifiable concentrate Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 230000006378 damage Effects 0.000 description 9
- 230000002538 fungal effect Effects 0.000 description 9
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
- 239000004033 plastic Substances 0.000 description 9
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- 239000000047 product Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 239000000080 wetting agent Substances 0.000 description 9
- 239000005909 Kieselgur Substances 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
- 230000002363 herbicidal effect Effects 0.000 description 8
- 239000004563 wettable powder Substances 0.000 description 8
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 7
- 239000004927 clay Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 6
- 241001157813 Cercospora Species 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 231100000674 Phytotoxicity Toxicity 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 5
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- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 5
- 150000004996 alkyl benzenes Chemical class 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 5
- MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 5
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- 238000006722 reduction reaction Methods 0.000 description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
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- 239000010452 phosphate Substances 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 239000010665 pine oil Substances 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- CODMKWVXOBTMKC-UHFFFAOYSA-N propan-2-yl n-(3,4-diethoxy-5-formylphenyl)carbamate Chemical compound CCOC1=CC(NC(=O)OC(C)C)=CC(C=O)=C1OCC CODMKWVXOBTMKC-UHFFFAOYSA-N 0.000 description 1
- OIKORXDYWNEWGW-UHFFFAOYSA-N propan-2-yl n-(3-chloro-4-ethoxy-5-ethylphenyl)carbamate Chemical compound CCOC1=C(Cl)C=C(NC(=O)OC(C)C)C=C1CC OIKORXDYWNEWGW-UHFFFAOYSA-N 0.000 description 1
- UFSQBQXLOFNISM-UHFFFAOYSA-N propan-2-yl n-(4-ethoxy-3-ethyl-5-methylphenyl)carbamate Chemical compound CCOC1=C(C)C=C(NC(=O)OC(C)C)C=C1CC UFSQBQXLOFNISM-UHFFFAOYSA-N 0.000 description 1
- ZYHMJXZULPZUED-UHFFFAOYSA-N propargite Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1C(OS(=O)OCC#C)CCCC1 ZYHMJXZULPZUED-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- 235000015523 tannic acid Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- 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
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/20—N-Aryl derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/04—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/28—Radicals substituted by nitrogen atoms
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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5830381A JPS57171951A (en) | 1981-04-16 | 1981-04-16 | N-phenylcarbamate compound, its preparation, and agent for controlling pesticide-resistant microorganism containing said compound as active component |
| JP17850981A JPS5879968A (ja) | 1981-11-06 | 1981-11-06 | Ｎ−フエニルカ−バメ−ト系化合物、その製造法およびそれを有効成分とする農園芸用殺菌剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS269982A2 CS269982A2 (en) | 1985-08-15 |
| CS243472B2 true CS243472B2 (en) | 1986-06-12 |
Family
ID=26399358
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS822699A CS243472B2 (en) | 1981-04-16 | 1982-04-15 | Fungicide and method of its efficient substance's production |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4482546A (xx) |
| EP (1) | EP0063905B1 (xx) |
| KR (1) | KR890000367B1 (xx) |
| AR (1) | AR242087A1 (xx) |
| AU (1) | AU549369B2 (xx) |
| BG (3) | BG40807A3 (xx) |
| BR (1) | BR8202224A (xx) |
| CA (1) | CA1249286A (xx) |
| CS (1) | CS243472B2 (xx) |
| DE (1) | DE3265364D1 (xx) |
| EG (1) | EG15715A (xx) |
| ES (1) | ES511463A0 (xx) |
| GB (1) | GB2101584B (xx) |
| GR (1) | GR76473B (xx) |
| HU (1) | HU192750B (xx) |
| IL (1) | IL65489A0 (xx) |
| KE (1) | KE3518A (xx) |
| NZ (1) | NZ200242A (xx) |
| PH (1) | PH17743A (xx) |
| RO (1) | RO85070B (xx) |
| TR (1) | TR21732A (xx) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4690946A (en) * | 1981-04-16 | 1987-09-01 | Sumitomo Chemical Company, Limited | Fungicidal N-phenylcarbamates |
| OA07237A (en) * | 1981-10-29 | 1984-04-30 | Sumitomo Chemical Co | Fungicidical N-phenylcarbamates. |
| US4710514A (en) * | 1982-05-04 | 1987-12-01 | Sumitomo Chemical Company, Limited | Fungicidal carbamates and thiolcarbamates |
| EP0106326A1 (en) * | 1982-10-15 | 1984-04-25 | Sumitomo Chemical Company, Limited | 1-Amino or nitro-3,5-disubstituted-4-ethoxybenzenes and their production |
| GB8300713D0 (en) * | 1983-01-12 | 1983-02-16 | Sumitomo Chemical Co | Fungicidal aniline derivatives |
| AU570420B2 (en) * | 1983-01-13 | 1988-03-17 | Sumitomo Chemical Company, Limited | Fungicidal aniline derivatives |
| OA07768A (fr) * | 1983-05-12 | 1985-08-30 | Sumitomo Chemical Co | Dérivés d'anillines fongicides. |
| GB8315495D0 (en) * | 1983-06-06 | 1983-07-13 | Sumitomo Chemical Co | Fungicidal aniline derivatives |
| US5142094A (en) * | 1989-11-06 | 1992-08-25 | Warner-Lambert Company | Aryl substituted carbamate derivatives which are acat inhibitors |
| CA2269627A1 (en) * | 1997-08-25 | 1999-03-04 | Itsuo Nagai | Polyester film for electrical insulation |
| UA73307C2 (uk) * | 1999-08-05 | 2005-07-15 | Куміаі Кемікал Індастрі Ко., Лтд. | Похідна карбамату і фунгіцид сільськогосподарського/садівницького призначення |
| NZ545547A (en) * | 2003-08-29 | 2009-07-31 | Mitsui Chemicals Inc | Insecticide for agricultural or horticultural use and method of use thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3408384A (en) * | 1963-08-08 | 1968-10-29 | Shell Oil Co | 4-methoxy-3, 5-dimethylphenyl methylcarbamate |
| US3660465A (en) * | 1969-08-01 | 1972-05-02 | Stauffer Chemical Co | Ethynylene containing n-phenyl carbamates |
| BE755687A (fr) * | 1969-09-04 | 1971-03-03 | Ciba Geigy | Esters carboxyliques portant des substituants et servant comme agents synergiques a des substances insecticides et/ou acaricides |
| US3852332A (en) * | 1972-06-30 | 1974-12-03 | American Cyanamid Co | Esters of (alkynloxy) and (alkenyloxy) carbanilic acid |
| DE2921130A1 (de) * | 1979-05-25 | 1980-12-11 | Basf Ag | N-arylthiolcarbamate |
-
1982
- 1982-04-06 NZ NZ200242A patent/NZ200242A/en unknown
- 1982-04-08 AU AU82476/82A patent/AU549369B2/en not_active Ceased
- 1982-04-09 GR GR67863A patent/GR76473B/el unknown
- 1982-04-12 US US06/367,404 patent/US4482546A/en not_active Expired - Fee Related
- 1982-04-12 KR KR8201601A patent/KR890000367B1/ko active
- 1982-04-13 PH PH27127A patent/PH17743A/en unknown
- 1982-04-13 IL IL65489A patent/IL65489A0/xx not_active IP Right Cessation
- 1982-04-13 EG EG201/82A patent/EG15715A/xx active
- 1982-04-15 RO RO107274A patent/RO85070B/ro unknown
- 1982-04-15 HU HU821154A patent/HU192750B/hu not_active IP Right Cessation
- 1982-04-15 CS CS822699A patent/CS243472B2/cs unknown
- 1982-04-15 ES ES511463A patent/ES511463A0/es active Granted
- 1982-04-15 CA CA000401095A patent/CA1249286A/en not_active Expired
- 1982-04-16 AR AR82289127A patent/AR242087A1/es active
- 1982-04-16 BG BG8362429A patent/BG40807A3/xx unknown
- 1982-04-16 BG BG8256263A patent/BG40646A3/xx unknown
- 1982-04-16 TR TR21732A patent/TR21732A/xx unknown
- 1982-04-16 BG BG8362428A patent/BG40806A3/xx unknown
- 1982-04-16 DE DE8282301983T patent/DE3265364D1/de not_active Expired
- 1982-04-16 BR BR8202224A patent/BR8202224A/pt not_active IP Right Cessation
- 1982-04-16 EP EP82301983A patent/EP0063905B1/en not_active Expired
- 1982-04-16 GB GB08211121A patent/GB2101584B/en not_active Expired
-
1985
- 1985-03-22 KE KE3518A patent/KE3518A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PH17743A (en) | 1984-11-27 |
| EG15715A (en) | 1989-01-30 |
| CA1249286A (en) | 1989-01-24 |
| BG40806A3 (en) | 1987-02-16 |
| AR242087A1 (es) | 1993-03-31 |
| GR76473B (xx) | 1984-08-10 |
| TR21732A (tr) | 1985-05-17 |
| ES8306716A1 (es) | 1983-06-01 |
| KR890000367B1 (ko) | 1989-03-14 |
| RO85070A (ro) | 1984-08-17 |
| GB2101584B (en) | 1985-02-06 |
| AU549369B2 (en) | 1986-01-23 |
| GB2101584A (en) | 1983-01-19 |
| NZ200242A (en) | 1985-08-30 |
| US4482546A (en) | 1984-11-13 |
| EP0063905A1 (en) | 1982-11-03 |
| BR8202224A (pt) | 1983-03-29 |
| ES511463A0 (es) | 1983-06-01 |
| AU8247682A (en) | 1983-04-21 |
| IL65489A0 (en) | 1982-07-30 |
| DE3265364D1 (de) | 1985-09-19 |
| HU192750B (en) | 1987-07-28 |
| CS269982A2 (en) | 1985-08-15 |
| BG40807A3 (en) | 1987-02-16 |
| BG40646A3 (en) | 1986-01-15 |
| KR830010098A (ko) | 1983-12-26 |
| KE3518A (en) | 1985-04-19 |
| EP0063905B1 (en) | 1985-08-14 |
| RO85070B (ro) | 1984-09-30 |
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