CA1185247A - 1-phenyl-2-triazolyl-pent-1-en-3-ones substituees et leur preparation - Google Patents

1-phenyl-2-triazolyl-pent-1-en-3-ones substituees et leur preparation

Info

Publication number: CA1185247A
Authority: CA; Canada
Prior art keywords: radical; chlorine; phenyl; fluorine; alkyl
Prior art date: 1980-11-28
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

CA000441920A

Other languages

English (en)

Inventor

Erik Regel

Karl H. Buchel

Klaus Lurssen

Paul-Ernst Frohberger

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.)

Bayer AG

Original Assignee

Bayer AG

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.)

1980-11-28

Filing date

1983-11-24

Publication date

1985-04-09

1980-11-28 Priority claimed from DE19803044802 external-priority patent/DE3044802A1/de

1983-11-24 Application filed by Bayer AG filed Critical Bayer AG

1985-04-09 Application granted granted Critical

1985-04-09 Publication of CA1185247A publication Critical patent/CA1185247A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 17
230000008569 process Effects 0.000 title claims abstract description 13
FEIUYLCFTVVSBF-UHFFFAOYSA-N 1-phenyl-2-(2h-triazol-4-yl)pent-1-en-3-one Chemical class C1=NNN=C1C(C(=O)CC)=CC1=CC=CC=C1 FEIUYLCFTVVSBF-UHFFFAOYSA-N 0.000 title claims abstract 3
238000004519 manufacturing process Methods 0.000 title claims description 6
150000001875 compounds Chemical class 0.000 claims abstract description 98
-1 halogenoalkylthio Chemical group 0.000 claims abstract description 58
125000000217 alkyl group Chemical group 0.000 claims abstract description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 15
KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims abstract description 8
JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims abstract description 7
125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 5
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 5
125000005843 halogen group Chemical group 0.000 claims abstract description 5
125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 3
125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 3
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims abstract 2
239000002904 solvent Substances 0.000 claims description 24
229910052801 chlorine Inorganic materials 0.000 claims description 20
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 18
229910052731 fluorine Inorganic materials 0.000 claims description 18
239000011737 fluorine Substances 0.000 claims description 18
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
239000000460 chlorine Substances 0.000 claims description 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 9
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 9
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
229910052794 bromium Inorganic materials 0.000 claims description 8
125000001309 chloro group Chemical group Cl* 0.000 claims description 8
239000003054 catalyst Substances 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
150000001299 aldehydes Chemical class 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
150000003254 radicals Chemical class 0.000 claims description 3
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 3
HNVIQLPOGUDBSU-UHFFFAOYSA-N 2,6-dimethylmorpholine Chemical compound CC1CNCC(C)O1 HNVIQLPOGUDBSU-UHFFFAOYSA-N 0.000 claims description 2
239000002841 Lewis acid Substances 0.000 claims description 2
150000007517 lewis acids Chemical group 0.000 claims description 2
RAIYODFGMLZUDF-UHFFFAOYSA-N piperidin-1-ium;acetate Chemical compound CC([O-])=O.C1CC[NH2+]CC1 RAIYODFGMLZUDF-UHFFFAOYSA-N 0.000 claims description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
CPHXLFKIUVVIOQ-UHFFFAOYSA-N 2-(trifluoromethoxy)benzaldehyde Chemical group FC(F)(F)OC1=CC=CC=C1C=O CPHXLFKIUVVIOQ-UHFFFAOYSA-N 0.000 claims 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
HXELGNKCCDGMMN-UHFFFAOYSA-N [F].[Cl] Chemical compound [F].[Cl] HXELGNKCCDGMMN-UHFFFAOYSA-N 0.000 claims 1
125000004093 cyano group Chemical group *C#N 0.000 claims 1
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 21
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LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 5
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ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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Agricultural Chemicals And Associated Chemicals (AREA)

CA000441920A 1980-11-28 1983-11-24 1-phenyl-2-triazolyl-pent-1-en-3-ones substituees et leur preparation Expired CA1185247A (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DEP3044802.3		1980-11-28
DE19803044802 DE3044802A1 (de)	1980-11-28	1980-11-28	Substituierte 1-phenyl-2-triazolyl-1-penten-3-ole, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenwachstumsregulatoren und fungizide
CA000391066A CA1169075A (fr)	1980-11-28	1981-11-27	Obtention et emploi comme agents regulateurs de la croissance vegetale et comme fongicides de phenyl-2- triazolyl-pent-1-en-3-ols a substitution en 1

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000391066A Division CA1169075A (fr)	1980-11-28	1981-11-27	Obtention et emploi comme agents regulateurs de la croissance vegetale et comme fongicides de phenyl-2- triazolyl-pent-1-en-3-ols a substitution en 1

Publications (1)

Publication Number	Publication Date
CA1185247A true CA1185247A (fr)	1985-04-09

Family

ID=25669494

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000441920A Expired CA1185247A (fr)	1980-11-28	1983-11-24	1-phenyl-2-triazolyl-pent-1-en-3-ones substituees et leur preparation

Country Status (1)

Country	Link
CA (1)	CA1185247A (fr)

1983
- 1983-11-24 CA CA000441920A patent/CA1185247A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2002-04-09	MKEX	Expiry

Publication	Publication Date	Title
CA1341164C (fr)	2001-01-02	Derives de 1-hydroxyethyl-azole, procede pour leur preparation et leur utilisation en tant que regulateurs de croissance des plantes et fongicides
US4904296A (en)	1990-02-27	Fungicidal and plant growth-regulating novel substituted 1-hydroxyalkyl-azolyl derivatives
US4868196A (en)	1989-09-19	Ether derivatives of substituted 1-hydroxyalkyl- azoles as fungicides and plant growth regulators
CA1157027A (fr)	1983-11-15	Triazolylmethyle tertiobutylcarbinols substitues, methode pour les preparer; leur utilisation comme agents pour la protection des plantes et comme produits intermediaires
JPH0224823B2 (fr)	1990-05-30
CA1168248A (fr)	1984-05-29	Procede d'obtention de derives de triazolylpropenol; emploi comme regulateurs de la croissance vegetale et comme fongicides
US4729783A (en)	1988-03-08	Halogenated triazolylvinyl keto and carbinol compounds and plant growth regulant and fungicidal compositions
CA1185608A (fr)	1985-04-16	Azolyl-alkenones et azolyl-alkenols, procede de preparation et utilisation comme regulateurs de la croissance des plantes et fongicides
IE51123B1 (en)	1986-10-15	Substituted triazolylmethyl-tert.-butyl-carbinols,a process for their preparation and their use as plant protection agents and as intermediate products
US4507141A (en)	1985-03-26	Triazolylalkyl-thioether plant growth regulators and fungicides
US4875928A (en)	1989-10-24	Substituted azolylcyclopropyl-azolylmethyl-carbinol derivatives
CA1167039A (fr)	1984-05-08	Ethers benzylpyrimidinylalkyliques; methode de preparation et utilisation comme regulateurs de la croissance des plantes et comme fongicides; produits intermediaires et leur preparation
US4584373A (en)	1986-04-22	1-(substituted-phenoxy)-3-methyl-2-(pyrimidin-5-yl)-butan-2-ol useful as plant growth regulating agents
CA1169075A (fr)	1984-06-12	Obtention et emploi comme agents regulateurs de la croissance vegetale et comme fongicides de phenyl-2- triazolyl-pent-1-en-3-ols a substitution en 1
CA1185247A (fr)	1985-04-09	1-phenyl-2-triazolyl-pent-1-en-3-ones substituees et leur preparation
US4622064A (en)	1986-11-11	Triazolo-(3,2-c)perhydroxazin-8-one derivatives and use as fungicides and plant growth regulators
JPH0238589B2 (fr)	1990-08-31
CA1229615A (fr)	1987-11-24	Derives de substitution d'azolylvinyl-cetones ou -carbinols