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EP1272475A1 - 2-phenyle-2h-pyridazine-3-one - Google Patents

2-phenyle-2h-pyridazine-3-one

Info

Publication number
EP1272475A1
EP1272475A1 EP01929551A EP01929551A EP1272475A1 EP 1272475 A1 EP1272475 A1 EP 1272475A1 EP 01929551 A EP01929551 A EP 01929551A EP 01929551 A EP01929551 A EP 01929551A EP 1272475 A1 EP1272475 A1 EP 1272475A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
alkoxy
butyl
compounds
aminocarbonyl
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.)
Withdrawn
Application number
EP01929551A
Other languages
German (de)
English (en)
Inventor
Michael Puhl
Thorsten Volk
Gerhard Hamprecht
Robert Reinhard
Ingo Sagasser
Cyrill Zagar
Matthias Witschel
Helmut Walter
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.)
BASF SE
Original Assignee
BASF SE
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.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP1272475A1 publication Critical patent/EP1272475A1/fr
Withdrawn legal-status Critical Current

Links

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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D237/14—Oxygen atoms

Definitions

  • Aminocarbonyl-C 1 -C 4 -alkyl (-C-C 4 -alkyl) aminocarbonyl-C ⁇ -C -alkyl, di- (C ⁇ -C -alkyl) aminocarbonyl-C ⁇ -C 4 -alkyl, C ⁇ -C -haloalkoxy- C 1 -C 4 alkyl, C 1 -C 4 alkoxy-C 1 -C 4 alkoxy C 1 -C 4 alkyl,
  • C -C 4 alkylamino) carbonyl-C ⁇ -C 4 -alkyl for: by (C ⁇ -C 4 -alkylamino) carbonyl such as CO-NH-CH 3 , CO-NH-C 2 H 5 , n- Propylaminocabonyl, CO-NH-CH (CH 3 ) 2 , CO-NH-CH 2 CH 2 -C 2 H 5 , CO-NH-CH (CH 3 ) -C 2 H 5 , CO-NH-CH 2 -CH (CH 3 ) 2 or CO-NH-C (CH 3 ) 3 , preferably CO-NH-CH 3 or CO-NH-C 2 H 5 , substituted C ⁇ -C 4 alkyl, for example for CH 2 -CO- NH-CH 3 , CH 2 -CO-NH-C 2 H 5 , CH 2 -CO-NH-CH 2 -C 2 H 5 , CH 2 -CO-NH-CH (CH 3 ) 2 , CH 2 -CO
  • C -C 4 -Alkylthio carbonyl-C ⁇ -C -alkoxy-C ⁇ -C -alkyl C ⁇ -C 4 -alkylthiocarbonyl in the alkoxy part substituted by C ⁇ -C 4 -alkoxy-C ⁇ -C 4 -alkyl, e.g. , B. -CH 2 CH 2 -0-CH 2 C (0) -SCH 3 or -CH 2 CH 2 -0-CH (CH 3 ) C (0) -SCH 3 ;
  • C 3 -C 8 cycloalkoxy is substituted, e.g. B. cyclopropoxymethyl, cyclobutoxy ethyl, cyclopentoxymethyl, cyclohexyloxymethyl, cycloheptyloxymethyl, cyclooctyloxymethyl, 2- (cyclopropyloxyethyl, 2- (cyclobutyloxy) ethyl, 2- (cyclopentyloxy) ethyl, 2- (cyclohexyloxy) ethyl, 2- (cycloheptyloxy ) ethyl, 2- (cyclooctyloxyethyl, 3- (cyclopropyloxy) propyl, 3- (cyclobutyloxy) propyl, 3- (cyclopentyloxy) propyl, 3- (cyclohexyloxy) propyl, 3- (cyclo-heptyloxy) propyl, 3- (Cyclooctyloxy) propyl,
  • C 3 -C 8 cycloalkoxy for: cyclopropoxy, cyclobutoxy, cyclopentoxy, cyclohexoxy, cycloheptoxy or cyclooctoxy;
  • R 3 preferably has the following meanings:
  • a further preferred class of 2-phenyl-2H-pyridazin-3-ones according to the invention are those compounds of the general formula I in which Z represents a group NR 6 .
  • R 6 is preferably C ⁇ -C 4 alkoxy.
  • R 2 then represents a group OR 7 , in which R 7 has the meanings mentioned above and in particular C für-C-alkyl, C ⁇ -C -haloalkyl, C ⁇ -C -alkyloxycarbonyl-C ⁇ -C 4 - alkyl or C ⁇ -C 4 -Halogenalkyloxycarbonyl-C ⁇ -C 4 alkyl.
  • a further advantageous embodiment of this reaction consists of initially introducing the acid I "in the alcohol H ⁇ R 3 intended for esterification or a mixture of this alcohol with one of the abovementioned solvents and reacting it in situ with thionyl chloride.
  • the fall-off is based on the formation of separating tissue between the fruit, leaf and sprout part of the plants and is promoted by the 2-phenyl-2H-pyridazin-3-ones of the general formula I and their salts according to the invention.
  • the use of the 2-phenyl-2H-pyridazin-3-ones of the general formula I according to the invention and their agriculturally useful salts thus permits controlled fall-off of fruits and controlled defoliation of useful plants such as cotton (defoliation) and thus enables such crop plants a harvest relief.
  • the compounds I according to the invention can be formulated, for example, as follows:
  • the compound la.34 was prepared by reacting the acid chloride Ia.42 with methylglycinate.
  • Plastic pots with loamy sand with about 3.0% humus as substrate served as culture vessels.
  • the seeds of the test plants were sown separately according to species.
  • the plants used in the greenhouse experiments are composed of the following types:
  • the young cotton plants were treated to runoff with an aqueous preparation of the respective active ingredient, which additionally contained 0.15% by weight, based on the total weight of the preparation, of a fatty alcohol ethoxylate (Plurafac® LF 700).
  • the amount of water applied was about 1000 l / ha. After 13 days, the number of leaves dropped and the degree of defoliation were determined. The untreated control plants showed no defoliation.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne la 2-phényle-2H-pyridazine-3-one de la formule générale (I), les variables R<1>, R<2>, X, Y et Z ayant la signification suivante : X est de l'halogène, Y est du fluor ou du chlore, Z est de l'oxygène, R<1> est de l'hydrogène ou C1-C4-alkyle, R<2> est du chlore, OR<3> ou NR<4>R<5>, R<3>, R<4> et R<5> ayant les significations données dans la revendication 1, et Z peut également être un groupe NR<6> lorsque R<2> est un groupe OR<7>, R<6> et R<7> ayant les significations données dans la revendication 1. L'invention concerne également des sels d'usage agricole des composés de la formule générale (I). L'invention concerne par ailleurs l'utilisation de composés (I) et leurs sels en tant qu'herbicides et/ou pour la dessiccation et/ou la défoliation de plantes, et des agents herbicides et des agents de dessiccation et/ou de défoliation de plantes contenant les composés (I) et/ou leurs sels en tant qu'agents actifs. L'invention concerne enfin des procédés destinés à la lutte contre des plantes parasites (plantes nuisibles) et à la dessiccation et/ou défoliation de plantes au moyen des composés (I) et/ou de leurs sels.
EP01929551A 2000-04-14 2001-04-12 2-phenyle-2h-pyridazine-3-one Withdrawn EP1272475A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10018632 2000-04-14
DE10018632 2000-04-14
PCT/EP2001/004213 WO2001079182A1 (fr) 2000-04-14 2001-04-12 2-phenyle-2h-pyridazine-3-one

Publications (1)

Publication Number Publication Date
EP1272475A1 true EP1272475A1 (fr) 2003-01-08

Family

ID=7638819

Family Applications (1)

Application Number Title Priority Date Filing Date
EP01929551A Withdrawn EP1272475A1 (fr) 2000-04-14 2001-04-12 2-phenyle-2h-pyridazine-3-one

Country Status (5)

Country Link
US (1) US20030162662A1 (fr)
EP (1) EP1272475A1 (fr)
AU (1) AU2001256287A1 (fr)
CA (1) CA2406217A1 (fr)
WO (1) WO2001079182A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6822016B2 (en) 2001-09-10 2004-11-23 Johnson & Johnson Vision Care, Inc. Biomedical devices containing internal wetting agents
US20060100408A1 (en) * 2002-03-11 2006-05-11 Powell P M Method for forming contact lenses comprising therapeutic agents
US8157012B2 (en) * 2007-09-07 2012-04-17 Frazier W Lynn Downhole sliding sleeve combination tool

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19520613A1 (de) * 1995-06-06 1996-12-12 Bayer Ag Phenylpyridazinone
NZ315400A (en) * 1995-08-21 2000-01-28 Sumitomo Chemical Co Pyridazin-3-one derivatives, their use, and intermediates for their production
CN1305466A (zh) * 1998-04-09 2001-07-25 拜尔公司 取代的苯基哒嗪酮类化合物
AU2001262197A1 (en) * 2000-04-14 2001-10-30 Basf Aktiengesellschaft 2-phenyl-2h-pyridazine-3-ones

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0179182A1 *

Also Published As

Publication number Publication date
AU2001256287A1 (en) 2001-10-30
US20030162662A1 (en) 2003-08-28
CA2406217A1 (fr) 2001-10-25
WO2001079182A1 (fr) 2001-10-25

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Inventor name: WITSCHEL, MATTHIAS

Inventor name: ZAGAR, CYRILL

Inventor name: WALTER, HELMUT

Inventor name: HAMPRECHT, GERHARD

Inventor name: SAGASSER, INGO

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Inventor name: REINHARD, ROBERT

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