DD150746A5 - Verfahren zur herstellung von 4-thiazolidinonen - Google Patents

Verfahren zur herstellung von 4-thiazolidinonen Download PDF

Info

Publication number: DD150746A5
Authority: DD; German Democratic Republic
Prior art keywords: pyridyl; thiazolidinone; methyl; pyridylcarboxaldehyde; chlorophenyl
Prior art date: 1978-10-16

Application number

DD79220571A

Other languages

German (de)

English (en)

Inventor

Eriks V Krumkalns

Original Assignee

Lilly Co Eli

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.)

1978-10-16

Filing date

1979-10-16

Publication date

1981-09-16

1979-10-16 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1981-09-16 Publication of DD150746A5 publication Critical patent/DD150746A5/de

Links

238000000034 method Methods 0.000 title claims description 29
238000002360 preparation method Methods 0.000 title claims description 28
PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 claims abstract description 84
CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims abstract description 76
QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 claims abstract description 75
238000006243 chemical reaction Methods 0.000 claims abstract description 11
IXDRVFHZVJDSQV-UHFFFAOYSA-N 3-(4-chlorophenyl)-5-methyl-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound O=C1C(C)SC(C=2C=NC=CC=2)N1C1=CC=C(Cl)C=C1 IXDRVFHZVJDSQV-UHFFFAOYSA-N 0.000 claims abstract description 10
YMVFJGSXZNNUDW-UHFFFAOYSA-N (4-chlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1 YMVFJGSXZNNUDW-UHFFFAOYSA-N 0.000 claims abstract description 4
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 claims abstract description 4
LVVQHDBPUGBITE-UHFFFAOYSA-N 3-[(4-chlorophenyl)methyl]-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound C1=CC(Cl)=CC=C1CN1C(=O)CSC1C1=CC=CN=C1 LVVQHDBPUGBITE-UHFFFAOYSA-N 0.000 claims abstract description 3
-1 trifluoromethylphenyl Chemical group 0.000 claims description 129
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
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PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 6
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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
BMJBELLWVIGIMS-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)CSC1C1=CC=CN=C1 BMJBELLWVIGIMS-UHFFFAOYSA-N 0.000 claims description 5
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DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical compound ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
CSGRSRYPHUABSU-UHFFFAOYSA-N n-phenyl-1-pyridin-2-ylmethanimine Chemical class C=1C=CC=NC=1C=NC1=CC=CC=C1 CSGRSRYPHUABSU-UHFFFAOYSA-N 0.000 description 1
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VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 1
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YNOGYQAEJGADFJ-UHFFFAOYSA-N oxolan-2-ylmethanamine Chemical compound NCC1CCCO1 YNOGYQAEJGADFJ-UHFFFAOYSA-N 0.000 description 1
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BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
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239000011591 potassium Substances 0.000 description 1
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235000014483 powder concentrate Nutrition 0.000 description 1
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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238000001953 recrystallisation Methods 0.000 description 1
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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
- A01N47/02—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 no bond to a nitrogen atom
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/86—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3

Landscapes

Life Sciences & Earth Sciences (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Agronomy & Crop Science (AREA)
General Health & Medical Sciences (AREA)
Pest Control & Pesticides (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

DD79220571A 1978-10-16 1979-10-16 Verfahren zur herstellung von 4-thiazolidinonen DD150746A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US95170878A	1978-10-16	1978-10-16

Publications (1)

Publication Number	Publication Date
DD150746A5 true DD150746A5 (de)	1981-09-16

Family

ID=25492046

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
DD79220571A DD150746A5 (de)	1978-10-16	1979-10-16	Verfahren zur herstellung von 4-thiazolidinonen
DD79220572A DD150747A5 (de)	1978-10-16	1979-10-16	Verfahren zur herstellung von thiazinonen
DD79216255A DD146539A5 (de)	1978-10-16	1979-10-16	Fungizides oder wachstumsregulierendes mittel

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
DD79220572A DD150747A5 (de)	1978-10-16	1979-10-16	Verfahren zur herstellung von thiazinonen
DD79216255A DD146539A5 (de)	1978-10-16	1979-10-16	Fungizides oder wachstumsregulierendes mittel

Country Status (28)

Country	Link
EP (1)	EP0010420B1 (fr)
JP (1)	JPS5555184A (fr)
AR (1)	AR225154A1 (fr)
AT (1)	ATA670079A (fr)
AU (1)	AU5165479A (fr)
BE (1)	BE879368A (fr)
BR (1)	BR7906634A (fr)
CH (1)	CH643842A5 (fr)
CS (1)	CS216535B2 (fr)
DD (3)	DD150746A5 (fr)
DE (1)	DE2967188D1 (fr)
DK (1)	DK434779A (fr)
ES (2)	ES485073A1 (fr)
FI (1)	FI793191A7 (fr)
FR (1)	FR2439197B1 (fr)
GB (1)	GB2031892B (fr)
GR (1)	GR71652B (fr)
HU (2)	HU187550B (fr)
IE (1)	IE48966B1 (fr)
IL (1)	IL58446A (fr)
LU (1)	LU81779A1 (fr)
NZ (1)	NZ191818A (fr)
PH (1)	PH15765A (fr)
PL (2)	PL125628B1 (fr)
PT (2)	PT70314A (fr)
RO (4)	RO82467A (fr)
SU (1)	SU1079175A3 (fr)
ZA (1)	ZA795488B (fr)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4443455A (en) *	1978-02-17	1984-04-17	Imperial Chemical Industries Plc	Fungidical thiazolidinones
US4443454A (en) *	1978-02-17	1984-04-17	Imperial Chemical Industries Plc	Thiazolidinones
US4482712A (en) *	1978-10-16	1984-11-13	Eli Lilly And Company	Substituted 1-thia-3-aza-4-ones
EP0062612A1 (fr) *	1981-04-02	1982-10-13	Ciba-Geigy Ag	Dérivés de thiazolines
CA1229337A (fr) *	1982-04-02	1987-11-17	Pieter T. Haken	Composes heterocycliques fungicides
JPS6061580A (ja) *	1983-09-16	1985-04-09	Zenyaku Kogyo Kk	新規１，４−チアジン誘導体とその製造法
JPS63225373A (ja) *	1986-07-24	1988-09-20	Sumitomo Pharmaceut Co Ltd	新規チアゾリジン−４−オン誘導体およびその酸付加塩
US4992455A (en) *	1987-05-22	1991-02-12	Sumitomo Pharmaceuticals Company, Limited	Thiazolidin-4-one derivatives useful for treating diseases caused by platelet activating factor
US5021435A (en) *	1988-01-22	1991-06-04	Sumitomo Pharmaceuticals Company, Limited	Certain pyridyl-thiazolidin-4-one having anti-ulcer activity
ES2104641T3 (es) *	1990-10-17	1997-10-16	Hoechst Schering Agrevo Gmbh	Derivados de pirimidina, procedimientos para su preparacion, agentes que los contienen y su utilizacion como fungicidas.
DE4243818A1 (de) *	1992-12-23	1994-06-30	Bayer Ag	5-Aryl-1,3-thiazin-Derivate
US6174908B1 (en)	1999-05-10	2001-01-16	Icagen, Inc.	Potassium channel inhibitors
CA2334258A1 (fr)	1998-06-05	1999-12-09	Icagen, Inc.	Inhibiteurs des canaux de potassium
US6506751B1 (en)	1999-11-12	2003-01-14	Millennium Pharmaceuticals, Inc.	Thiazolidinone compounds useful as chemokine inhibitors
TWI394753B (zh) *	2006-03-17	2013-05-01	Otsuka Pharma Co Ltd	新穎替妥牟拉（ｔｅｔｏｍｉｌａｓｔ）晶體
CN117143090A (zh) *	2023-08-14	2023-12-01	中国科学院海洋研究所	含呋喃杂环的4-噻唑烷酮类化合物及其制备方法与应用

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2910479A (en) *	1958-01-06	1959-10-27	Ciba Pharm Prod Inc	Certain 4-pyridyl thiazoline-2-ones and process
CH433322A (de) *	1964-04-16	1967-04-15	Dresden Arzneimittel	Verfahren zur Herstellung von peripher gefässerweiternd wirksamen Salzen des 2-(Pyridyl-(3'))-thiazolin- 2
US3574841A (en) *	1968-03-05	1971-04-13	Mobil Oil Corp	Fungicidal methods using substituted nitropyridines
CA962269A (en) *	1971-05-05	1975-02-04	Uniroyal Ltd.	Thiazoles, and their use as insecticides
GB1539726A (en) *	1974-12-31	1979-01-31	Nitidandhaprabhas O	Treatment of animals suffering from mange
FR2356423A1 (fr) *	1976-07-01	1978-01-27	Oeriu Simion	Derives de l'acide thiazolidinecarboxylique, leur preparation et leur application comme medicaments
EP0004129B1 (fr) *	1978-02-17	1983-06-08	Imperial Chemical Industries Plc	Dérivés de thiazolidinone, procédé pour leur préparation, compositions pesticides les contenant et procédés pour le traitement des plantes

1979
- 1979-10-10 CS CS796885A patent/CS216535B2/cs unknown
- 1979-10-10 AU AU51654/79A patent/AU5165479A/en not_active Abandoned
- 1979-10-10 NZ NZ191818A patent/NZ191818A/xx unknown
- 1979-10-11 LU LU81779A patent/LU81779A1/fr unknown
- 1979-10-11 AR AR278464A patent/AR225154A1/es active
- 1979-10-12 BE BE1/9563A patent/BE879368A/fr not_active IP Right Cessation
- 1979-10-12 PH PH23161A patent/PH15765A/en unknown
- 1979-10-14 IL IL58446A patent/IL58446A/xx unknown
- 1979-10-15 BR BR7906634A patent/BR7906634A/pt unknown
- 1979-10-15 ZA ZA00795488A patent/ZA795488B/xx unknown
- 1979-10-15 GB GB7935748A patent/GB2031892B/en not_active Expired
- 1979-10-15 RO RO79105702A patent/RO82467A/fr unknown
- 1979-10-15 GR GR60266A patent/GR71652B/el unknown
- 1979-10-15 RO RO79105701A patent/RO82359A/fr unknown
- 1979-10-15 RO RO7998944A patent/RO78232A/fr unknown
- 1979-10-15 RO RO7998943A patent/RO78231A/fr unknown
- 1979-10-15 DK DK434779A patent/DK434779A/da not_active Application Discontinuation
- 1979-10-15 AT AT0670079A patent/ATA670079A/de not_active Application Discontinuation
- 1979-10-15 FI FI793191A patent/FI793191A7/fi not_active Application Discontinuation
- 1979-10-15 SU SU792831951A patent/SU1079175A3/ru active
- 1979-10-15 PT PT70314A patent/PT70314A/pt unknown
- 1979-10-15 EP EP79302215A patent/EP0010420B1/fr not_active Expired
- 1979-10-15 FR FR7925597A patent/FR2439197B1/fr not_active Expired
- 1979-10-15 HU HU79@@84165A patent/HU187550B/hu unknown
- 1979-10-15 DE DE7979302215T patent/DE2967188D1/de not_active Expired
- 1979-10-15 CH CH931179A patent/CH643842A5/fr not_active IP Right Cessation
- 1979-10-15 PT PT70313A patent/PT70313A/pt unknown
- 1979-10-15 IE IE1949/79A patent/IE48966B1/en unknown
- 1979-10-15 HU HU79EI884A patent/HU185844B/hu unknown
- 1979-10-16 ES ES485073A patent/ES485073A1/es not_active Expired
- 1979-10-16 DD DD79220571A patent/DD150746A5/de unknown
- 1979-10-16 JP JP13410079A patent/JPS5555184A/ja active Pending
- 1979-10-16 PL PL1979218994A patent/PL125628B1/pl unknown
- 1979-10-16 DD DD79220572A patent/DD150747A5/de unknown
- 1979-10-16 PL PL1979231659A patent/PL127226B1/pl unknown
- 1979-10-16 DD DD79216255A patent/DD146539A5/de unknown
- 1979-10-16 ES ES485072A patent/ES485072A0/es active Granted

Also Published As

Publication number	Publication date
IE791949L (en)	1980-04-16
RO78232A (fr)	1982-02-01
JPS5555184A (en)	1980-04-22
DE2967188D1 (en)	1984-09-27
RO82467A (fr)	1983-09-26
BR7906634A (pt)	1980-07-08
IE48966B1 (en)	1985-06-26
PT70313A (en)	1979-11-01
DD146539A5 (de)	1981-02-18
ES8200105A1 (es)	1980-12-01
PL127226B1 (en)	1983-10-31
EP0010420B1 (fr)	1984-08-22
NZ191818A (en)	1982-05-25
RO82467B (ro)	1983-08-30
DK434779A (da)	1980-04-17
FR2439197A1 (fr)	1980-05-16
HU185844B (en)	1985-04-28
IL58446A (en)	1983-10-31
RO78231A (fr)	1982-02-01
FR2439197B1 (fr)	1986-04-25
PH15765A (en)	1983-03-24
EP0010420A1 (fr)	1980-04-30
LU81779A1 (fr)	1980-01-24
BE879368A (fr)	1980-04-14
PL125628B1 (en)	1983-06-30
GB2031892A (en)	1980-04-30
DD150747A5 (de)	1981-09-16
HU187550B (en)	1986-01-28
GR71652B (fr)	1983-06-20
CH643842A5 (fr)	1984-06-29
RO82359B (ro)	1983-07-30
AR225154A1 (es)	1982-02-26
RO82359A (fr)	1983-08-03
PT70314A (en)	1979-11-01
IL58446A0 (fr)	1980-01-31
ZA795488B (en)	1981-05-27
GB2031892B (en)	1983-08-17
ATA670079A (de)	1983-05-15
CS216535B2 (en)	1982-11-26
AU5165479A (en)	1980-04-24
PL218994A1 (fr)	1980-07-01
ES485073A1 (es)	1980-10-01
SU1079175A3 (ru)	1984-03-07
FI793191A7 (fi)	1981-01-01
ES485072A0 (es)	1980-12-01

Publication	Publication Date	Title
DE60001241T2 (de)	2003-08-28	Heterocyclisch substituierte Isoxazolidine und ihre Verwendung als Fungizide
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.
DE2640730A1 (de)	1978-03-16	Heterocyclische phenylaether und diese enthaltende herbizide mittel
DD146539A5 (de)	1981-02-18	Fungizides oder wachstumsregulierendes mittel
DE2250077C2 (de)	1984-04-26	Pflanzenschutzmittel auf Basis eines s-Triazolo[3,4-b]benzoxazols oder s-Triazolo[3,4-b]benzthiazols und neue s-Triazolo[3,4-b]benzthiazole
DD144498A5 (de)	1980-10-22	Verfahren zur verringerung von herbizidschaeden
EP0279239A1 (fr)	1988-08-24	Agents microbicides
EP0011693A1 (fr)	1980-06-11	N-hétérocycles N-substitués par trifluorométhane-sulfonylaminophényle, leur préparation, compositions les contenant et leur utilisation pour la régulation de la croissance des plantes
DE2833274A1 (de)	1979-02-22	Imidazolinylbenzoate
EP0368212A2 (fr)	1990-05-16	Agents herbicides, contenant des dérivés des acides 2-(4-hétéroaryloxy)- ou 2-(4-aryloxy)-phénoxy-acétiques ou -propioniques et/ou des dérivés de la cyclohexénone comme matières actives et des dérivés du naphtalène comme antidotes
US4436739A (en)	1984-03-13	Substituted 1-thia-3-aza-4-ones
DE2637886A1 (de)	1977-03-10	3-pyridyl-oxy-alkancarbonsaeureamide
CH637386A5 (de)	1983-07-29	Benzoxazol- und benzothiazolderivate.
EP0400356B1 (fr)	1994-08-10	Sulfonamides
DE2744385C2 (de)	1986-12-18	Biocide Mittel und Verfahren zur Herstellung der darin enthaltenen Wirkstoffe
EP0151744B1 (fr)	1989-04-26	1-Acylimidazolinones, procédé de leur préparation et leur application dans l'agriculture
EP0032879A1 (fr)	1981-07-29	Dérivés de benzothiazolyl-urée, leur préparation, compositions les contenant et leur utilisation comme herbicides
DE69202059T2 (de)	1995-11-02	Propensäurederivate.
EP0037482B1 (fr)	1985-03-13	3,4,5,6-Tétrahydro-1,2,4,6-thiatriazine(3,5)dione-1,1-dioxides, leur préparation, les herbicides les contenant, procédé de préparation d'herbicides et procédé pour la lutte contre la croissance de la végétation indésirable
EP0216299A1 (fr)	1987-04-01	Dérivés de la quinoxaline, leur procédé de préparation et leur utilisation pour protéger les plantes cultivées contre l'effet phytotoxique d'herbicides
EP0401582B1 (fr)	1994-07-20	Dérivés de quinoline fusés avec des noyaux hétérocycliques à cinq membres
EP0457714A1 (fr)	1991-11-21	Dérivés de thiadiazabicyclononane, leur procédé de préparation, intermédiaires et leur application comme herbicides
US4482712A (en)	1984-11-13	Substituted 1-thia-3-aza-4-ones
EP0011802B1 (fr)	1982-09-15	Amides d'acides phénoxy-phénoxy-propioniques, procédés pour leur préparation, compositions herbicides les contenant et leur application à la lutte contre les mauvaises herbes