SU1496633A3 - Способ получени производных тиофена - Google Patents

Способ получени производных тиофена Download PDF

Info

Publication number: SU1496633A3
Authority: SU; USSR - Soviet Union
Prior art keywords: cyano; carbon atoms; unsubstituted; substituted; halogen
Prior art date: 1986-02-19

Application number

SU874028996A

Other languages

English (en)

Russian (ru)

Inventor

Долман Хендрик

Кэйперс Йоханнес

Original Assignee

Дюфар Интернэшнл Рисерч Б.В. (Фирма)

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.)

1986-02-19

Filing date

1987-02-16

Publication date

1989-07-23

1987-02-16 Application filed by Дюфар Интернэшнл Рисерч Б.В. (Фирма) filed Critical Дюфар Интернэшнл Рисерч Б.В. (Фирма)

1989-07-23 Application granted granted Critical

1989-07-23 Publication of SU1496633A3 publication Critical patent/SU1496633A3/ru

Links

238000000034 method Methods 0.000 title claims abstract description 6
150000003577 thiophenes Chemical class 0.000 title claims abstract description 5
-1 phenylthio phenyl Chemical group 0.000 claims abstract description 8
125000004432 carbon atom Chemical group C* 0.000 claims abstract 10
229910052736 halogen Inorganic materials 0.000 claims abstract 7
125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract 6
125000000217 alkyl group Chemical group 0.000 claims abstract 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract 4
150000002367 halogens Chemical class 0.000 claims abstract 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 4
125000004093 cyano group Chemical group *C#N 0.000 claims abstract 3
125000003342 alkenyl group Chemical group 0.000 claims abstract 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 2
125000005843 halogen group Chemical group 0.000 claims abstract 2
125000002883 imidazolyl group Chemical group 0.000 claims abstract 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 2
230000003647 oxidation Effects 0.000 claims abstract 2
238000007254 oxidation reaction Methods 0.000 claims abstract 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract 2
125000001425 triazolyl group Chemical group 0.000 claims abstract 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
150000001345 alkine derivatives Chemical class 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 claims 1
125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
125000003277 amino group Chemical group 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 21
238000002360 preparation method Methods 0.000 abstract description 7
230000000694 effects Effects 0.000 abstract description 4
230000000844 anti-bacterial effect Effects 0.000 abstract description 2
230000000855 fungicidal effect Effects 0.000 abstract description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
125000000446 sulfanediyl group Chemical group *S* 0.000 abstract 1
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 5
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
241000233866 Fungi Species 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
238000010953 Ames test Methods 0.000 description 2
231100000039 Ames test Toxicity 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
241000233639 Pythium Species 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
230000002538 fungal effect Effects 0.000 description 2
244000000004 fungal plant pathogen Species 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000000243 solution Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
229930192474 thiophene Natural products 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
WYJOVVXUZNRJQY-UHFFFAOYSA-N 2-Acetylthiophene Chemical compound CC(=O)C1=CC=CS1 WYJOVVXUZNRJQY-UHFFFAOYSA-N 0.000 description 1
CHHWTBPYLYKNAA-UHFFFAOYSA-N 2-methylsulfinyl-5-methylsulfonylthiophene-3-carbonitrile Chemical compound CS(=O)C=1SC(S(C)(=O)=O)=CC=1C#N CHHWTBPYLYKNAA-UHFFFAOYSA-N 0.000 description 1
LPTSFXAAEDZKRD-UHFFFAOYSA-N 3-amino-5-ethylsulfinylthiophene-2,4-dicarbonitrile Chemical compound CCS(=O)C=1SC(C#N)=C(N)C=1C#N LPTSFXAAEDZKRD-UHFFFAOYSA-N 0.000 description 1
ALMGZUKDHHNTJA-UHFFFAOYSA-N 3-amino-5-hexylsulfinylthiophene-2,4-dicarbonitrile Chemical compound CCCCCCS(=O)C=1SC(C#N)=C(N)C=1C#N ALMGZUKDHHNTJA-UHFFFAOYSA-N 0.000 description 1
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BOYYYGKUMPGTTF-UHFFFAOYSA-N 4-amino-5-(4-chlorobenzoyl)-2-ethylsulfinylthiophene-3-carbonitrile Chemical compound N#CC1=C(S(=O)CC)SC(C(=O)C=2C=CC(Cl)=CC=2)=C1N BOYYYGKUMPGTTF-UHFFFAOYSA-N 0.000 description 1
GHHDVPUWXNFGQW-UHFFFAOYSA-N 4-amino-5-benzoyl-2-butylsulfinylthiophene-3-carbonitrile Chemical compound N#CC1=C(S(=O)CCCC)SC(C(=O)C=2C=CC=CC=2)=C1N GHHDVPUWXNFGQW-UHFFFAOYSA-N 0.000 description 1
IGSJQEBHYUHAGQ-UHFFFAOYSA-N 4-amino-5-formyl-2-methylsulfinylthiophene-3-carbonitrile Chemical compound CS(=O)C=1SC(C=O)=C(N)C=1C#N IGSJQEBHYUHAGQ-UHFFFAOYSA-N 0.000 description 1
DJYVXBJLHPKUKS-UHFFFAOYSA-N 4-bromothiophene-2-carbonitrile Chemical compound BrC1=CSC(C#N)=C1 DJYVXBJLHPKUKS-UHFFFAOYSA-N 0.000 description 1
MAHCPFGFSUMBNN-UHFFFAOYSA-N 4-chloro-2-ethylsulfinyl-5-formylthiophene-3-carbonitrile Chemical compound CCS(=O)C=1SC(C=O)=C(Cl)C=1C#N MAHCPFGFSUMBNN-UHFFFAOYSA-N 0.000 description 1
SNRSMFOWZRLXIG-UHFFFAOYSA-N 4-chloro-2-ethylsulfonyl-5-methylsulfonylthiophene-3-carbonitrile Chemical compound CCS(=O)(=O)C=1SC(S(C)(=O)=O)=C(Cl)C=1C#N SNRSMFOWZRLXIG-UHFFFAOYSA-N 0.000 description 1
QUOPDPOOLBKIIO-UHFFFAOYSA-N 4-chloro-2-methylsulfinyl-1-benzothiophene-3-carbonitrile Chemical compound C1=CC(Cl)=C2C(C#N)=C(S(=O)C)SC2=C1 QUOPDPOOLBKIIO-UHFFFAOYSA-N 0.000 description 1
AUQSUNGGSNZZBR-UHFFFAOYSA-N 4-chloro-5-(4-chlorobenzoyl)-2-methylsulfinylthiophene-3-carbonitrile Chemical compound N#CC1=C(S(=O)C)SC(C(=O)C=2C=CC(Cl)=CC=2)=C1Cl AUQSUNGGSNZZBR-UHFFFAOYSA-N 0.000 description 1
125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 description 1
BRTGVOUFYKFPQV-UHFFFAOYSA-N 5-(4-chlorobenzoyl)-2-ethylsulfinyl-4-methoxythiophene-3-carbonitrile Chemical compound N#CC1=C(S(=O)CC)SC(C(=O)C=2C=CC(Cl)=CC=2)=C1OC BRTGVOUFYKFPQV-UHFFFAOYSA-N 0.000 description 1
BOIHBYUVRGQDBY-UHFFFAOYSA-N 5-(4-chlorobenzoyl)-2-ethylsulfinylthiophene-3-carbonitrile Chemical compound N#CC1=C(S(=O)CC)SC(C(=O)C=2C=CC(Cl)=CC=2)=C1 BOIHBYUVRGQDBY-UHFFFAOYSA-N 0.000 description 1
MXOFAZFPRVSCIU-UHFFFAOYSA-N 5-(4-chlorobenzoyl)-2-methylsulfinylthiophene-3-carbonitrile Chemical compound N#CC1=C(S(=O)C)SC(C(=O)C=2C=CC(Cl)=CC=2)=C1 MXOFAZFPRVSCIU-UHFFFAOYSA-N 0.000 description 1
HYIKAEMKNFHDIT-UHFFFAOYSA-N 5-(4-chlorobenzoyl)-2-propylsulfinylthiophene-3-carbonitrile Chemical compound N#CC1=C(S(=O)CCC)SC(C(=O)C=2C=CC(Cl)=CC=2)=C1 HYIKAEMKNFHDIT-UHFFFAOYSA-N 0.000 description 1
YDUWFWGFXCSHLX-UHFFFAOYSA-N 5-(benzenesulfinyl)-3-chlorothiophene-2,4-dicarbonitrile Chemical compound ClC1=C(C#N)SC(S(=O)C=2C=CC=CC=2)=C1C#N YDUWFWGFXCSHLX-UHFFFAOYSA-N 0.000 description 1
SYRQXCDZTNMUAK-UHFFFAOYSA-N 5-(benzenesulfinyl)thiophene-2,4-dicarbonitrile Chemical compound C=1C=CC=CC=1S(=O)C=1SC(C#N)=CC=1C#N SYRQXCDZTNMUAK-UHFFFAOYSA-N 0.000 description 1
ZRIMRZGTVNCEQB-UHFFFAOYSA-N 5-(benzenesulfonyl)thiophene-2,4-dicarbonitrile Chemical compound C=1C=CC=CC=1S(=O)(=O)C=1SC(C#N)=CC=1C#N ZRIMRZGTVNCEQB-UHFFFAOYSA-N 0.000 description 1
ZQQDOVVFEMLFLP-UHFFFAOYSA-N 5-acetyl-2-butylsulfinyl-4-chlorothiophene-3-carbonitrile Chemical compound CCCCS(=O)C=1SC(C(C)=O)=C(Cl)C=1C#N ZQQDOVVFEMLFLP-UHFFFAOYSA-N 0.000 description 1
PIDFRHLNYKORIN-UHFFFAOYSA-N 5-acetyl-2-butylsulfinylthiophene-3-carbonitrile Chemical compound CCCCS(=O)C=1SC(C(C)=O)=CC=1C#N PIDFRHLNYKORIN-UHFFFAOYSA-N 0.000 description 1
WJVPCFSWGIKAMX-UHFFFAOYSA-N 5-acetyl-2-ethylsulfinyl-4-phenylthiophene-3-carbonitrile Chemical compound N#CC1=C(S(=O)CC)SC(C(C)=O)=C1C1=CC=CC=C1 WJVPCFSWGIKAMX-UHFFFAOYSA-N 0.000 description 1
XTDUISSEZXADIK-UHFFFAOYSA-N 5-acetyl-2-ethylsulfonylthiophene-3-carbonitrile Chemical compound CCS(=O)(=O)C=1SC(C(C)=O)=CC=1C#N XTDUISSEZXADIK-UHFFFAOYSA-N 0.000 description 1
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MINGJWSCYZKHJP-UHFFFAOYSA-N 5-acetyl-4-methoxy-2-methylsulfinylthiophene-3-carbonitrile Chemical compound COC1=C(C(C)=O)SC(S(C)=O)=C1C#N MINGJWSCYZKHJP-UHFFFAOYSA-N 0.000 description 1
KZGBGRJBMHFESD-UHFFFAOYSA-N 5-benzoyl-2-butylsulfinylthiophene-3-carbonitrile Chemical compound N#CC1=C(S(=O)CCCC)SC(C(=O)C=2C=CC=CC=2)=C1 KZGBGRJBMHFESD-UHFFFAOYSA-N 0.000 description 1
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BZSDJBSSKOBEPS-UHFFFAOYSA-N 5-benzoyl-2-ethylsulfinylthiophene-3-carbonitrile Chemical compound N#CC1=C(S(=O)CC)SC(C(=O)C=2C=CC=CC=2)=C1 BZSDJBSSKOBEPS-UHFFFAOYSA-N 0.000 description 1
XRSHOCDMHPUURD-UHFFFAOYSA-N 5-benzoyl-2-methylsulfinylthiophene-3-carbonitrile Chemical compound N#CC1=C(S(=O)C)SC(C(=O)C=2C=CC=CC=2)=C1 XRSHOCDMHPUURD-UHFFFAOYSA-N 0.000 description 1
BMJPITDYNAPACF-UHFFFAOYSA-N 5-benzoyl-4-chloro-2-ethylsulfinylthiophene-3-carbonitrile Chemical compound N#CC1=C(S(=O)CC)SC(C(=O)C=2C=CC=CC=2)=C1Cl BMJPITDYNAPACF-UHFFFAOYSA-N 0.000 description 1
NYXATPLTDOVXHC-UHFFFAOYSA-N 5-benzoyl-4-chloro-2-methylsulfinylthiophene-3-carbonitrile Chemical compound N#CC1=C(S(=O)C)SC(C(=O)C=2C=CC=CC=2)=C1Cl NYXATPLTDOVXHC-UHFFFAOYSA-N 0.000 description 1
DKSIWGFUXRYMEO-UHFFFAOYSA-N 5-benzoyl-4-methoxy-2-propylsulfinylthiophene-3-carbonitrile Chemical compound N#CC1=C(S(=O)CCC)SC(C(=O)C=2C=CC=CC=2)=C1OC DKSIWGFUXRYMEO-UHFFFAOYSA-N 0.000 description 1
IDXMOLJJIQHKNY-UHFFFAOYSA-N 5-benzylsulfinyl-3-chlorothiophene-2,4-dicarbonitrile Chemical compound ClC1=C(C#N)SC(S(=O)CC=2C=CC=CC=2)=C1C#N IDXMOLJJIQHKNY-UHFFFAOYSA-N 0.000 description 1
KDLMGCMFXAMLJV-UHFFFAOYSA-N 5-butylsulfinyl-3-chlorothiophene-2,4-dicarbonitrile Chemical compound CCCCS(=O)C=1SC(C#N)=C(Cl)C=1C#N KDLMGCMFXAMLJV-UHFFFAOYSA-N 0.000 description 1
CRCDYEUFQABCGZ-UHFFFAOYSA-N 5-butylsulfinylthiophene-2,4-dicarbonitrile Chemical compound CCCCS(=O)C=1SC(C#N)=CC=1C#N CRCDYEUFQABCGZ-UHFFFAOYSA-N 0.000 description 1
RYBRRURVLKVIEY-UHFFFAOYSA-N 5-ethylsulfinyl-3-phenoxythiophene-2,4-dicarbonitrile Chemical compound N#CC1=C(S(=O)CC)SC(C#N)=C1OC1=CC=CC=C1 RYBRRURVLKVIEY-UHFFFAOYSA-N 0.000 description 1
MQBSJISXCANKFX-UHFFFAOYSA-N 5-ethylsulfinyl-3-phenylthiophene-2,4-dicarbonitrile Chemical compound N#CC1=C(S(=O)CC)SC(C#N)=C1C1=CC=CC=C1 MQBSJISXCANKFX-UHFFFAOYSA-N 0.000 description 1
MGRLISUJIMOJFA-UHFFFAOYSA-N 5-ethylsulfonylthiophene-2,4-dicarbonitrile Chemical compound CCS(=O)(=O)C=1SC(C#N)=CC=1C#N MGRLISUJIMOJFA-UHFFFAOYSA-N 0.000 description 1
BBLUKVFPZIZDPE-UHFFFAOYSA-N 5-methylsulfinylthiophene-2,4-dicarbaldehyde Chemical compound CS(=O)C=1SC(C=O)=CC=1C=O BBLUKVFPZIZDPE-UHFFFAOYSA-N 0.000 description 1
SIJUAPWHBCUIND-UHFFFAOYSA-N 5-methylsulfinylthiophene-2,4-dicarbonitrile Chemical compound CS(=O)C=1SC(C#N)=CC=1C#N SIJUAPWHBCUIND-UHFFFAOYSA-N 0.000 description 1
NIXCABSRUUGYRY-UHFFFAOYSA-N 5-propylsulfinylthiophene-2,4-dicarbonitrile Chemical compound CCCS(=O)C=1SC(C#N)=CC=1C#N NIXCABSRUUGYRY-UHFFFAOYSA-N 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
241000223194 Fusarium culmorum Species 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
241000607142 Salmonella Species 0.000 description 1
206010042434 Sudden death Diseases 0.000 description 1
DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000008272 agar Substances 0.000 description 1
229940041514 candida albicans extract Drugs 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
RISHDEPWUFIFMH-UHFFFAOYSA-N ethyl 3-amino-4-cyano-5-methylsulfinylthiophene-2-carboxylate Chemical compound CCOC(=O)C=1SC(S(C)=O)=C(C#N)C=1N RISHDEPWUFIFMH-UHFFFAOYSA-N 0.000 description 1
PAKUODMWKSEYFE-UHFFFAOYSA-N ethyl 3-chloro-4-cyano-5-ethylsulfinylthiophene-2-carboxylate Chemical compound CCOC(=O)C=1SC(S(=O)CC)=C(C#N)C=1Cl PAKUODMWKSEYFE-UHFFFAOYSA-N 0.000 description 1
239000008103 glucose Substances 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
239000000203 mixture Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
QGMRQYFBGABWDR-UHFFFAOYSA-N sodium;5-ethyl-5-pentan-2-yl-1,3-diazinane-2,4,6-trione Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)NC1=O QGMRQYFBGABWDR-UHFFFAOYSA-N 0.000 description 1
239000002689 soil Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000012138 yeast extract Substances 0.000 description 1

Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SU874028996A 1986-02-19 1987-02-16 Способ получени производных тиофена SU1496633A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
NL8600416		1986-02-19

Publications (1)

Publication Number	Publication Date
SU1496633A3 true SU1496633A3 (ru)	1989-07-23

Family

ID=19847598

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU874028996A SU1496633A3 (ru)	1986-02-19	1987-02-16	Способ получени производных тиофена

Country Status (5)

Country	Link
JP (1)	JPS62192353A (cs)
CS (1)	CS268823B2 (cs)
DD (1)	DD265315A5 (cs)
SU (1)	SU1496633A3 (cs)
ZA (1)	ZA871109B (cs)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
RU2164916C2 (ru) *	1995-02-01	2001-04-10	Хехст АГ	Замещенные тиофенсульфонилмочевины, способ их получения и лекарственное средство
RU2403248C2 (ru) *	2006-04-17	2010-11-10	Мицуи Кемикалз, Инк.	Производное 2-алкенил-3-аминотиофена и способ его получения

1987
- 1987-02-16 SU SU874028996A patent/SU1496633A3/ru active
- 1987-02-16 ZA ZA871109A patent/ZA871109B/xx unknown
- 1987-02-17 CS CS871037A patent/CS268823B2/cs unknown
- 1987-02-18 DD DD30001687A patent/DD265315A5/de not_active IP Right Cessation
- 1987-02-19 JP JP3685787A patent/JPS62192353A/ja active Pending

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Вейганд-Хильгетаг. Методы эксперимента в органической химии. М., Хими , 1968, с. 611-613. *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
RU2164916C2 (ru) *	1995-02-01	2001-04-10	Хехст АГ	Замещенные тиофенсульфонилмочевины, способ их получения и лекарственное средство
RU2403248C2 (ru) *	2006-04-17	2010-11-10	Мицуи Кемикалз, Инк.	Производное 2-алкенил-3-аминотиофена и способ его получения

Also Published As

Publication number	Publication date
CS103787A2 (en)	1989-09-12
JPS62192353A (ja)	1987-08-22
CS268823B2 (en)	1990-04-11
DD265315A5 (de)	1989-03-01
ZA871109B (en)	1987-10-28

Publication	Publication Date	Title
CA1050558A (en)	1979-03-13	N-(substituted phenyl)-n-furanoyl-alanine methyl esters and their use in fungicidal compositions and methods
NO133402B (cs)	1976-01-19
JP2764265B2 (ja)	1998-06-11	殺微生物剤組成物
FR2458545A1 (fr)	1981-01-02	Procede de preparation de derives de benzylimidazole, nouveaux produits ainsi obtenus, et leur utilisation pour leurs activites antimycotique et fongicide
SU1050564A3 (ru)	1983-10-23	Способ получени производных нитротиофена
US3741981A (en)	1973-06-26	N-phenylsuccinimide derivatives
EP0524041B1 (fr)	1995-09-20	Pesticides
SU1313347A3 (ru)	1987-05-23	Способ получени производных триазола
CN113278020A (zh)	2021-08-20	含酰基硫脲结构的pityriacitrin生物碱衍生物及其制备方法和用途
FR2561239A1 (fr)	1985-09-20	Arylthio-pyridinyl-alcanols
DE2902832C2 (cs)	1989-07-13
CN1062551C (zh)	2001-02-28	萘醌衍生物
US4150144A (en)	1979-04-17	3-Phenyl-oxazolidine-2,4-dione microbicides
EP0112262A1 (fr)	1984-06-27	Nouveaux dérivés de la benzylcarbamoylpyridine
TWI920095B (zh)	2026-04-01	人類用抗真菌劑
CH640700A5 (fr)	1984-01-31	Composes et composition fongicide.
EP0101288A2 (en)	1984-02-22	Aryl(aryloxy or arylthio)azolomethanes, their preparation and their use
EP0566455B1 (fr)	1996-03-06	Nouveaux dérivés de l'acide 7-éthynyl alpha-(méthoxyméthylène) 1-naphtalène acétique, leur procédé de préparation et leur application comme pesticides
FR2582647A1 (fr)	1986-12-05	Derives du phenanthrene, leur procede de preparation et compositions fongicides les contenant
JPS6030673B2 (ja)	1985-07-17	抗かび活性を有するエテニルイミダゾ−ル誘導体、その製造法、およびそれを含む製薬組成物その製造に有用な中間物、およびこの中間物の製造法
IL35440A (en)	1973-11-28	Amidophenylguanidines, their production and use as fungicides
BE886127A (fr)	1981-05-13	Nouveaux derives de l'imidazole, leur preparation et leur application comme agents fongicides
EP0805795A1 (fr)	1997-11-12	Nouveaux amides aromatiques, leur procede de preparation, les compositions les contenant et leur utilisation comme pesticides
US4181732A (en)	1980-01-01	1-Branched-alkylcarbonyl-3-(3,5-dihalophenyl)imidazolidine-2,4-diones
RU2012560C1 (ru)	1994-05-15	Способ получения производных хлорметилхинолина

SU1496633A3 - Способ получени производных тиофена - Google Patents

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ID=19847598

Family Applications (1)

Country Status (5)

Cited By (2)

Non-Patent Citations (1)

Cited By (2)

Also Published As

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