JPS62916B2 - - Google Patents

Info

Publication number: JPS62916B2
Authority: JP; Japan
Prior art keywords: dichlorophenyl; general formula; perhydroimidazo; compound; parts
Prior art date: 1978-09-20
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

Application number

JP53115372A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5543010A (en

Inventor

Taichiro Shigematsu

Kenji Yoshida

Makoto Nakazawa

Hiroyuki Kasugai

Masataka Tsuda

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Mitsubishi Kasei Corp

Original Assignee

Mitsubishi Kasei Corp

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.)

1978-09-20

Filing date

1978-09-20

Publication date

1987-01-10

1978-09-20 Application filed by Mitsubishi Kasei Corp filed Critical Mitsubishi Kasei Corp

1978-09-20 Priority to JP11537278A priority Critical patent/JPS5543010A/ja

1979-06-02 Priority to BR7904156A priority patent/BR7904156A/pt

1979-06-18 Priority to US06/049,620 priority patent/US4229461A/en

1979-06-29 Priority to DE7979102194T priority patent/DE2962041D1/de

1979-06-29 Priority to ES482567A priority patent/ES482567A1/es

1979-06-29 Priority to EP79102194A priority patent/EP0006633B1/de

1980-03-26 Publication of JPS5543010A publication Critical patent/JPS5543010A/ja

1987-01-10 Publication of JPS62916B2 publication Critical patent/JPS62916B2/ja

Status Granted legal-status Critical Current

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)

JP11537278A 1978-06-30 1978-09-20 Perhydroimidazothiazole derivative, its preparation and agricultural and horticultural fungicide containing the same Granted JPS5543010A (en)

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
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.
EP79102194A EP0006633B1 (de)	1978-06-30	1979-06-29	6-(3,5-Dichlorphenyl)perhydroimidazo(5,1-b)thiazol-Derivate, fungizide Zusammensetzungen und Verfahren zur Kontrolle von fungalen Infektionen bei Pflanzen

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 (de)	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 (de)

1978
- 1978-09-20 JP JP11537278A patent/JPS5543010A/ja active Granted

Also Published As

Publication number	Publication date
JPS5543010A (en)	1980-03-26

Publication	Publication Date	Title
KR960002556B1 (ko)	1996-02-22	이미다졸 화합물 및 이를 함유하는 유해 유기체 방제용 살균 조성물
DE3786185T2 (de)	1993-10-21	5H-1,3,4-Thiazol[3,2-a]pyrimidin-5-on-Derivate und diese enthaltende fungizide Zubereitungen.
DE3786365T2 (de)	1993-10-21	5H-1,3,4-Thiadiazolo[3,2-a]pyrimidin-5-on-Derivate und diese enthaltende Gartenbau- und landwirtschaftliche Fungizidmittel.
EP0334809B1 (de)	1994-06-15	Mittel zum Schutz von Pflanzen gegen Krankheiten
DE2250077A1 (de)	1973-04-19	Verfahren zur herstellung von benzoxazol- und benzthiazolverbindungen und ihre verwendung zum pflanzenschutz
JPH02157266A (ja)	1990-06-18	Ｎ−インダニルカルボン酸アミド誘導体およびこれを有効成分とする農園芸用殺菌剤
EP0387195B1 (de)	1994-07-27	Mittel zum Schutz von Pflanzen gegen Krankheiten
DE69603470T2 (de)	1999-11-18	Pyridinderivative und pestizide
EP0517660B1 (de)	1997-04-23	Benzo-1,2,3-thiadiazol-Derivate
EP0384889B1 (de)	1993-10-13	Mittel zum Schutz von Pflanzen gegen Krankheiten
JPS5953468A (ja)	1984-03-28	４−フエニルピラゾ−ル誘導体及び農園芸用殺菌剤
DE1670709A1 (de)	1970-12-03	Pestizide Mittel
JPS62916B2 (de)	1987-01-10
JPH089601B2 (ja)	1996-01-31	Ｎ‐インダニルカルボン酸アミド誘導体およびこれを有効成分とする農園芸用殺菌剤
JP2833817B2 (ja)	1998-12-09	４―エチル―３―（置換フェニル）―１―（３―トリフルオロメチルフェニル）―２―ピロリジノン誘導体、その製造法およびこれらを有効成分とする除草剤
DE3509437A1 (de)	1985-10-03	Thiocyanopyrimidinderivat, verfahren zu seiner herstellung und dieses enthaltende fungizide fuer die landwirtschaft und den gartenbau
US4229461A (en)	1980-10-21	Fungicidal 6-(3,5-dichlorophenyl)perhydroimidazo[5,1-b]thiazole derivatives
JPH0454173A (ja)	1992-02-21	光学活性なｎ―インダニルチアゾールカルボン酸アミド誘導体およびこれを有効成分とする農園芸用殺菌剤
JPH04108774A (ja)	1992-04-09	光学活性なｎ―インダニルニコチン酸アミド誘導体及びこれを有効成分とする農園芸用殺菌剤
JPS6047279B2 (ja)	1985-10-21	パ−ヒドロイミダゾチアゾ−ル誘導体、その製法及びそれを含む農園芸用殺菌剤
KR830000377B1 (ko)	1983-03-05	퍼하이드로 이미다조 티아졸유도체의 제조법
JPH05194449A (ja)	1993-08-03	３−（４−ブロモフエニル）−５−メチルスルホニル−１，２，４−チアジアゾール
CA1110631A (en)	1981-10-13	Fungicidal 6-(3,5-dichlorophenyl) perhydroimidazo [5,1-b] thiazole
HU180301B (en)	1983-02-28	Fungicide compositions containing 1-bracket-branched alkyl-carobnyl-bracket closed-3-bracket-3,5-dihalogeno-phenyl-bracket closed-imidasolidine-2,4-diones and process for producing the active agents
KR790001857B1 (ko)	1979-12-26	우레아 유도체의 제조방법