JPS62916B2 - - Google Patents
Info
- Publication number
- JPS62916B2 JPS62916B2 JP53115372A JP11537278A JPS62916B2 JP S62916 B2 JPS62916 B2 JP S62916B2 JP 53115372 A JP53115372 A JP 53115372A JP 11537278 A JP11537278 A JP 11537278A JP S62916 B2 JPS62916 B2 JP S62916B2
- Authority
- JP
- Japan
- Prior art keywords
- dichlorophenyl
- general formula
- perhydroimidazo
- compound
- parts
- 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
- -1 (3,5-dichlorophenyl)perhydroimidazo[5,1-b]thiazole derivative Chemical class 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 11
- 239000000417 fungicide Substances 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 230000000855 fungicidal effect Effects 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- LQZZYAJLICCBRO-UHFFFAOYSA-N 6-(3,5-dichlorophenyl)-3,5,7,7a-tetrahydro-2h-imidazo[5,1-b][1,3]thiazole Chemical class ClC1=CC(Cl)=CC(N2CN3CCSC3C2)=C1 LQZZYAJLICCBRO-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- ULSZVNJBVJWEJE-UHFFFAOYSA-N thiazolidine-2-carboxylic acid Chemical class OC(=O)C1NCCS1 ULSZVNJBVJWEJE-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 150000007979 thiazole derivatives Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 27
- 239000000203 mixture Substances 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- 238000009472 formulation Methods 0.000 description 11
- 201000010099 disease Diseases 0.000 description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000004094 surface-active agent Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 230000000887 hydrating effect Effects 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 235000012222 talc Nutrition 0.000 description 4
- 239000004563 wettable powder Substances 0.000 description 4
- XEFUJGURFLOFAN-UHFFFAOYSA-N 1,3-dichloro-5-isocyanatobenzene Chemical compound ClC1=CC(Cl)=CC(N=C=O)=C1 XEFUJGURFLOFAN-UHFFFAOYSA-N 0.000 description 3
- JLEMKZDHFGCHLO-UHFFFAOYSA-N 1,3-dichloro-5-isothiocyanatobenzene Chemical compound ClC1=CC(Cl)=CC(N=C=S)=C1 JLEMKZDHFGCHLO-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000645 desinfectant Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000001469 hydantoins Chemical class 0.000 description 3
- GTUDXRQDUASHFT-UHFFFAOYSA-N methyl 2-ethyl-1,3-thiazolidine-2-carboxylate Chemical compound COC(=O)C1(CC)NCCS1 GTUDXRQDUASHFT-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- FJIQTPGTRICJON-UHFFFAOYSA-N 2-ethyl-1,3-thiazolidine-2-carboxylic acid Chemical compound CCC1(C(O)=O)NCCS1 FJIQTPGTRICJON-UHFFFAOYSA-N 0.000 description 2
- TYEYBOSBBBHJIV-UHFFFAOYSA-N 2-oxobutanoic acid Chemical compound CCC(=O)C(O)=O TYEYBOSBBBHJIV-UHFFFAOYSA-N 0.000 description 2
- QNOHIQYKOJRZLK-UHFFFAOYSA-N 3-[(3,5-dichlorophenyl)carbamothioyl]-1,3-thiazolidine-2-carboxylic acid Chemical class OC(=O)C1SCCN1C(=S)NC1=CC(Cl)=CC(Cl)=C1 QNOHIQYKOJRZLK-UHFFFAOYSA-N 0.000 description 2
- DLDUNHSDRVITCH-UHFFFAOYSA-N 3-[(3,5-dichlorophenyl)carbamoyl]-1,3-thiazolidine-2-carboxylic acid Chemical class OC(=O)C1SCCN1C(=O)NC1=CC(Cl)=CC(Cl)=C1 DLDUNHSDRVITCH-UHFFFAOYSA-N 0.000 description 2
- HOXXGECSGWAGRX-UHFFFAOYSA-N 6-(3,5-dichlorophenyl)-5-sulfanylidene-3,7a-dihydro-2H-imidazo[5,1-b][1,3]thiazol-7-one Chemical class ClC=1C=C(C=C(C=1)Cl)N1C(N2C(SCC2)C1=O)=S HOXXGECSGWAGRX-UHFFFAOYSA-N 0.000 description 2
- 241001450781 Bipolaris oryzae Species 0.000 description 2
- 241001465180 Botrytis Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 244000000231 Sesamum indicum Species 0.000 description 2
- 235000003434 Sesamum indicum Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 235000012216 bentonite Nutrition 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 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 2
- 239000003350 kerosene Substances 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- JRJTUKVSRPUZTO-UHFFFAOYSA-N methyl 3-[(3,5-dichlorophenyl)carbamoyl]-2-ethyl-1,3-thiazolidine-2-carboxylate Chemical compound COC(=O)C1(CC)SCCN1C(=O)NC1=CC(Cl)=CC(Cl)=C1 JRJTUKVSRPUZTO-UHFFFAOYSA-N 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UPFFQWNDECRHRY-UHFFFAOYSA-N 2-[2-(dodecylamino)ethylamino]acetic acid Chemical compound CCCCCCCCCCCCNCCNCC(O)=O UPFFQWNDECRHRY-UHFFFAOYSA-N 0.000 description 1
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 1
- KDVFRMMRZOCFLS-UHFFFAOYSA-N 2-oxopentanoic acid Chemical compound CCCC(=O)C(O)=O KDVFRMMRZOCFLS-UHFFFAOYSA-N 0.000 description 1
- RGLAKWRQFBAVFN-UHFFFAOYSA-N 2-propyl-1,3-thiazolidine-2-carboxylic acid Chemical compound CCCC1(C(O)=O)NCCS1 RGLAKWRQFBAVFN-UHFFFAOYSA-N 0.000 description 1
- BXVKVOBCTCUEQD-UHFFFAOYSA-N 3,3a,4,5,6,6a-hexahydro-2h-imidazo[4,5-d][1,3]thiazole Chemical class N1CSC2NCNC21 BXVKVOBCTCUEQD-UHFFFAOYSA-N 0.000 description 1
- RRFFWUURBRERTJ-UHFFFAOYSA-N 3,7a-dihydro-2h-imidazo[5,1-b][1,3]thiazole-5,7-dione Chemical class C1CSC2C(=O)NC(=O)N21 RRFFWUURBRERTJ-UHFFFAOYSA-N 0.000 description 1
- XZGXGPIBEMPYSI-UHFFFAOYSA-N 5-sulfanylidene-3,7a-dihydro-2H-imidazo[5,1-b][1,3]thiazol-7-one Chemical compound S1C2N(CC1)C(NC2=O)=S XZGXGPIBEMPYSI-UHFFFAOYSA-N 0.000 description 1
- XPAHHGDAYPMJGS-UHFFFAOYSA-N 6-(3,5-dichlorophenyl)-7a-propyl-2,3-dihydroimidazo[5,1-b][1,3]thiazole-5,7-dione Chemical compound O=C1C2(CCC)SCCN2C(=O)N1C1=CC(Cl)=CC(Cl)=C1 XPAHHGDAYPMJGS-UHFFFAOYSA-N 0.000 description 1
- PYURGIHXHHTQSI-UHFFFAOYSA-N 6-(3,5-dichlorophenyl)-7a-propyl-5-sulfanylidene-2,3-dihydroimidazo[5,1-b][1,3]thiazol-7-one Chemical compound C(CC)C12SCCN1C(N(C2=O)C1=CC(=CC(=C1)Cl)Cl)=S PYURGIHXHHTQSI-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 244000291564 Allium cepa Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 244000141359 Malus pumila Species 0.000 description 1
- 206010027146 Melanoderma Diseases 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 241000220324 Pyrus Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 241001558929 Sclerotium <basidiomycota> Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 229940053195 antiepileptics hydantoin derivative Drugs 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000004071 biological effect Effects 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
- 239000003093 cationic surfactant Substances 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
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940097265 cysteamine hydrochloride Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- ZLMOWEKDPWQOGN-UHFFFAOYSA-N methyl 2-propyl-1,3-thiazolidine-2-carboxylate Chemical compound CCCC1(C(=O)OC)NCCS1 ZLMOWEKDPWQOGN-UHFFFAOYSA-N 0.000 description 1
- BKLQHSJOASPNOG-UHFFFAOYSA-N methyl 3-[(3,5-dichlorophenyl)carbamoyl]-2-propyl-1,3-thiazolidine-2-carboxylate Chemical compound CCCC1(C(=O)OC)SCCN1C(=O)NC1=CC(Cl)=CC(Cl)=C1 BKLQHSJOASPNOG-UHFFFAOYSA-N 0.000 description 1
- MWGAGTHUIYYAKF-UHFFFAOYSA-N methyl 3-propyl-1,3-thiazolidine-2-carboxylate Chemical compound CCCN1CCSC1C(=O)OC MWGAGTHUIYYAKF-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 238000007867 post-reaction treatment Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- SUBJHSREKVAVAR-UHFFFAOYSA-N sodium;methanol;methanolate Chemical compound [Na+].OC.[O-]C SUBJHSREKVAVAR-UHFFFAOYSA-N 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Landscapes
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11537278A JPS5543010A (en) | 1978-09-20 | 1978-09-20 | Perhydroimidazothiazole derivative, its preparation and agricultural and horticultural fungicide containing the same |
| BR7904156A BR7904156A (pt) | 1978-06-30 | 1979-06-02 | Processo para preparacao de um composto 9-(3,5-dicloro-fenil)-perhidro-imidazo-(5,1-b)tiazol,processo para combater infeccoes fungicas sobre plantas,e composicao fungicida |
| US06/049,620 US4229461A (en) | 1978-06-30 | 1979-06-18 | Fungicidal 6-(3,5-dichlorophenyl)perhydroimidazo[5,1-b]thiazole derivatives |
| EP79102194A EP0006633B1 (en) | 1978-06-30 | 1979-06-29 | 6-(3,5-dichlorophenyl)perhydroimidazo(5,1-b)thiazole derivatives, antifungal compositions and a method of controlling fungal infections in plants |
| DE7979102194T DE2962041D1 (en) | 1978-06-30 | 1979-06-29 | 6-(3,5-dichlorophenyl)perhydroimidazo(5,1-b)thiazole derivatives, antifungal compositions and a method of controlling fungal infections in plants |
| ES482567A ES482567A1 (es) | 1978-06-30 | 1979-06-29 | Procedimiento de preparar compuestos tiazolicos. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11537278A JPS5543010A (en) | 1978-09-20 | 1978-09-20 | Perhydroimidazothiazole derivative, its preparation and agricultural and horticultural fungicide containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5543010A JPS5543010A (en) | 1980-03-26 |
| JPS62916B2 true JPS62916B2 (cs) | 1987-01-10 |
Family
ID=14660889
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11537278A Granted JPS5543010A (en) | 1978-06-30 | 1978-09-20 | Perhydroimidazothiazole derivative, its preparation and agricultural and horticultural fungicide containing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5543010A (cs) |
-
1978
- 1978-09-20 JP JP11537278A patent/JPS5543010A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5543010A (en) | 1980-03-26 |
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