WO1994000436A1 - Derives d'ester propenoique possedant un groupe pyrazole, et leur utilisation - Google Patents

Derives d'ester propenoique possedant un groupe pyrazole, et leur utilisation Download PDF

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Publication number
WO1994000436A1
WO1994000436A1 PCT/KR1993/000052 KR9300052W WO9400436A1 WO 1994000436 A1 WO1994000436 A1 WO 1994000436A1 KR 9300052 W KR9300052 W KR 9300052W WO 9400436 A1 WO9400436 A1 WO 9400436A1
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WO
WIPO (PCT)
Prior art keywords
methyl
group
phenyl
compound
trifluoromethyl
Prior art date
Application number
PCT/KR1993/000052
Other languages
English (en)
Inventor
Ki Jun Hwang
Sung Soo Kim
Original Assignee
Korea Research Institute Of Chemical Technology
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 Korea Research Institute Of Chemical Technology filed Critical Korea Research Institute Of Chemical Technology
Priority to AU54187/94A priority Critical patent/AU5418794A/en
Publication of WO1994000436A1 publication Critical patent/WO1994000436A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or 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
    • C07D231/18—One oxygen or sulfur 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or 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
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms

Definitions

  • the present invention relates to novel propenoic ester derivatives having pyrazole group of the following general formula(I) which have active fungicidal properties.
  • R is hydrogen, one or more halogen atoms selected from the group consisting of fluorine and chlorine, methyl, lower alkyl, alkoxy, nitro or phenyl group ;
  • R j is methyl, lower alkyl, alkenyl, alkynyl, benzyl, aryl, phenyl, substituted phenyl or pyridyl group ;
  • R 2 and R 3 are hydrogen, halogen atoms, trifluoromethyl or haloalkyl group ;
  • X is carbon or nitrogen atom.
  • the term "lower alkyl group" referred above designates straight or branch chained alkyl and have from 1 to 6 carbon atoms.
  • the inventors of the present invention synthesized novel propenoic ester derivatives by using pyrazole compound which have not been so far known.
  • the objective of the present invention is to provide novel propenoic ester derivatives with strong fungicidal activities toward various fungi and broad fungicidal spectrum and a simple manufacturing process.
  • Another objective is to provide fungicidal compositions containing said derivatives as active compounds.
  • the present invention is identified as propenoic ester derivatives having pyrazole group which correspond to the following formula(I), and agricultural preparations containing compounds of formula(I) as active ingredient.
  • R, R l5 R 2 , R 3 and X are respectively defined as the above.
  • R is hydrogen or chlorine
  • R l is methyl or lower alkyl group
  • R 2 and R 3 are of same or different from either hydrogen atom and trifluoromethyl group
  • Propenoic ester derivatives of the present invention may be divided to the following formula(I-a) and (I-b) according to the position of substituents introduced in pyrazole group.
  • R, R- , R 2 , R 3 and X are respectively defined as the above.
  • propenoic ester derivatives of the above formula(I) can be prepared by reacting the substituted 2-methyloxalylbenzyl bromide of following formula(II) with the pyrazole compound of following formula(III) in the presence of potassium carbonate or sodium hydride to prepare glyoxylate derivatives of the following formula(IV) as intermediate compound and reacting the glyoxylate derivatives with methoxyl amine or methoxymethyltriphenylphosphine to give compounds of formula(I).
  • R, R,, R 2 , R 3 and X are respectively defined.
  • the compound of formula (II) is reacted with the same mole of the compound of formula (III) in the presence of potassium carbonate and sodium hydride of each 1-3 equivalence to obtain the compound of formula (IV).
  • the resulted compound of formula (IV) as an intermediate is reacted with methoxymethyltriphenylphosphine in an organic solvent such as tetrahydrofuran or diethyl ether, or with methoxylamine in an organic solvent such as dichloromethane, 1, 2-dichloroethane, ethanol, etc., to obtain the desired compound of formula (I).
  • the obtained compound (I) consists of steroisomers (cis- and trans- form) of the following structural formulas.
  • EXAMPLE 6 cis -Methyl -2- [2-(l -ethyl-3-trifluoromethyl-5-pyrazoyl)-methyl-phenyl]-3- methoxypropenoate (Comp. No. 13) trans-Methyl-2-[2-(l-ethyl-3-trifluoromethyl-5-pyrazoyl)-methyl-phenyl]-3- methoxypropenoate (Comp. No. 14)
  • Methyl-2-[2-(l-pyridyl-3-trifluoromethyl-5-pyrazoyl)-methyl-phenyl]-3- methoxypropenoate (Comp. No. 28)
  • methoxymethyltriphenylphosphonium chloride (216mg, 0.63 mmol) in tetrahydrofuran at -7813 was added dropwise sec-butyllithium (1.3M in cyclohexane, 500/"/, 0.66 mmol).
  • the compound(II) used for preparing glyoxylate of the formula(IV) may be synthesized by the methods disclosed in M. Ranbaud, M. Bakasse, CT.
  • organic solvent such as chlorobenzene, tetrahydrofuran, dimethylformamide, etc. may be used to convert the compound of
  • the compound of formula(II) which is the starting compound from this step may be used in molar equivalent with compound(III) and potassium carbonate and ⁇ C sodium hydride of 1 - 3 equivalents may be used respectively.
  • Novel glyoxylate derivatives of the following formula(IV-a) and (IV-b) as 1 5 obtained from the above manufacturing process are typically listed as the following Table 3 and 4. Table 3.
  • the present invention is directed to the fungicidal compositions comprising the fungicidal compound of the present invention as an active compound.
  • Said fungicidal compositions can be formulated in various forms, such as aqueous dispersions, emulsions, dusts, granules and so forth. These compositions are preferred to comprise one or more active compounds of the present invention with one or more suitable adjuvants such as carriers and diluents which are chemically inert to the active compound.
  • concentration of the active compound in a composition thereof with an adjuvant therefor can vary ; it is only necessary that the active compounds be present in sufficient amounts so as to make possible the application of a fungicidally effective dosage.
  • the amount of the active compound is preferred to range from 10 to 90% by weight.
  • said amount is preferred to range from 0.1 to 30% by weight, also in the case of granule compositions, the amount is preferred to range from 1 to 30% by weight.
  • the amount of the active compound in the compositions is somewhat variable according to the purposed use of the compositions.
  • Preferred carriers which are employed in the compositions according to the present invention are liquid earners which are selected from alcohols(i.e. monohydric alcohols like methanol, dihydric alcohols like ethyleneglycol, and trihydric alcohols like glycerine, etc.), ketones(i.e. acetone, methylethylketone, etc), ethers(i.e. dioxane, tetrahydrofuran, cellosolve, etc.), aliphatic hydrocarbons (i.e. gasoline, kerossene, etc.), hydrocarbon halides(i.e. chloroform, carbon tetrachloride, etc.), acid amides(i.e.
  • liquid carriers can be used separately or in company with one or more other liquid carriers.
  • the fungicidal composition of the present invention may include emulsifying agents, spreaders, dispersing agents or permeating agents. Also, the composition may include nonionic, anionic or cationic surfactants, for example, fatty acid soda or polyoxyalkylesters, alkylsulfonates or polyethyleneglycolethers.
  • one of the compounds of the present invention or compositions containing the same can be advantageously employed in combination with one or more additional known pesticidal compounds which are active agricultural chemicals.
  • additional pesticidal compounds may be insecticides, herbicides, plant hormones and sterilizers, and if necessary, fertilizers.
  • Composition 1 (Emulsion) Compound No. 1-1 20% (by weight) xylene 75% polyoxyethylen glycolether 5%
  • Composition 2 (Dusts)
  • composition 3 (Aqueous dispersion)
  • Composition 4 (Granules)
  • Compound No. 2-2 10% (by weight) sodium lignosulfonate 5% bentonite 85% ⁇ o
  • the foregoing components were kneaded using with water and formed into a granule composition.
  • the superior fungicidal activities of propenoic ester derivatives(I) according to the present invention prepared by the above examples were tested to check protective 15 effect against the barley powdery mildew, the wheat leat rust, the rice blast and rice sheath blight.
  • a 10% acetone solution containing the compound(I) was diluted using Tween-20 solution of 250 ppm strength(500 ppm in the case of rice).
  • Five hundred ml of this chemical solution was sprayed to plants of equal height and allowed to stand at room temperature for 24 hours. After evaporation of spray solution and water, the 0 test plants were inoculated with target fungi. The tests were carried out two times by the same method.
  • the concentration of the test chemicals was gradually reduced until the EC 50 value, namely the concentration(ppm) which gives an fungicidal rate of 50%, was determined. 5
  • Pyricularia oryzae Cavara KJ301 as test rice blast fungus was selected and inoculated on rice polish agar medium(Rice polish 20g, Dextrose lOg, Agar 15g, D.W. lhr) to incubate at 2613 for 2 weeks, and then scratched airial mycelia with Rubber
  • Polishman were irradiated with near fluorescent light to form spore at 25 - 2813 for 48 hours.
  • a suspension of conidia in water(10 6 spoies/mZ) was prepared and sprayed upon the 3 -4 leaf stage of rice plants on the foliage. After placing in dark dew chamber for 24hours, the treated plants were then held in lighted growth chamber(26 ⁇ 213 ,
  • Rhizoctonia solani AG-1 was incubated in wheat bran medium (1 / , bottle), and then the agar disc was inoculated in growth chamber(27 ⁇ 113 ) for 7 days.
  • Rice plans in the 2 - 3 leaf stage in 5cm pots were inoculated with the milled conidia.
  • dew chamber(28 ⁇ 113 ) After incubating in dew chamber(28 ⁇ 113 ), the disease severity was examined against the percent disease area on the applied leaf of 2 - 3 leaf stage and compared to the standard rating diagram.
  • the plants After placing the treated wheat in dew chamber at 2013 for 1 day, the plants was held in growth chamber(20l3 , 70%) for 10 days, and then rated on the disease severity.
  • the disease severity was examined as the percent disease area after inoculating the spores for 10 days.
  • the treated barley was held in growth chamber(22 - 2413 , 50%), and the disease severity was rated after 7 days inoculation.
  • EC 50 value means the concentration(ppm) which a fungicidal rate of 50%.
  • the fungicidal rate of the test chemicals was determined according to the following ;
  • Control value(%) ( 1 ) x 100 Percent of disease area in untreated contral

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

Abstract

Nouveaux dérivés d'ester propénoïque possédant un groupe pyrazole répondant à la formule générale (I) et présentant une activité fongicide. Dans ladite formule, R représente hydrogène, un ou plusieurs atomes d'halogène sélectionnés dans le groupe constitué de fluor et de chlore, méthyle, alkyle inférieur, alcoxy, nitro ou un groupe phényle; R1 représente méthyle, alkyle inférieur, alcényle, alcynyle, benzyle, aryle, phényle, phényle substitué ou un groupe pyridyle; R2 et R3, identiques ou différents, représentent hydrogène, des atomes d'halogène, trifluorométhyle ou un groupe haloalkyle; et X représente un atome de carbone ou d'azote.
PCT/KR1993/000052 1992-06-25 1993-06-23 Derives d'ester propenoique possedant un groupe pyrazole, et leur utilisation WO1994000436A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU54187/94A AU5418794A (en) 1992-06-25 1993-06-23 Propenoic ester derivatives having pyrazole group and the use

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1019920011150A KR950006150B1 (ko) 1992-06-25 1992-06-25 피라졸을 함유한 프로페노익 에스테르 유도체
KR1992/11150 1992-06-25

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KR (1) KR950006150B1 (fr)
AU (1) AU5418794A (fr)
WO (1) WO1994000436A1 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995025095A1 (fr) * 1994-03-15 1995-09-21 Korea Research Institute Of Chemical Technology Derives d'ester propenoique possedant un groupe 4-hydroxypyrazole, et application
WO1996037477A1 (fr) * 1995-05-24 1996-11-28 Basf Aktiengesellschaft Esters d'acide azolyloxybenzyl-alcoxyacrylique, leur procede de fabrication et leur utilisation
FR2773155A1 (fr) * 1997-12-29 1999-07-02 Rhone Poulenc Agrochimie Nouveaux composes fongicides
WO2001044238A1 (fr) * 1999-12-13 2001-06-21 Bayer Aktiengesellschaft Benzylethers de pyrazolyle
WO2001046153A1 (fr) * 1999-12-20 2001-06-28 Bayer Aktiengesellschaft Derives ethers pyrazolylbenzyliques comportant un groupe fluoromethoxy et leur utilisation comme parasiticide
WO2015016335A1 (fr) * 2013-07-31 2015-02-05 住友化学株式会社 Composé tétrazolinone et son utilisation
WO2015041360A1 (fr) * 2013-09-20 2015-03-26 住友化学株式会社 Composé de tétrazolinone et son utilisation

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0278595A2 (fr) * 1987-02-09 1988-08-17 Zeneca Limited Fongicides
EP0350691A2 (fr) * 1988-07-15 1990-01-17 BASF Aktiengesellschaft Esters de l'acide alpha-aryl-acrylique substitués par un hétérocycle et fongicides contenant ces composés
DE3905948A1 (de) * 1989-02-25 1990-08-30 Basf Ag Substituierte n-hydroxypyrazole und fungizide, die diese verbindungen enthalten

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0278595A2 (fr) * 1987-02-09 1988-08-17 Zeneca Limited Fongicides
EP0350691A2 (fr) * 1988-07-15 1990-01-17 BASF Aktiengesellschaft Esters de l'acide alpha-aryl-acrylique substitués par un hétérocycle et fongicides contenant ces composés
DE3905948A1 (de) * 1989-02-25 1990-08-30 Basf Ag Substituierte n-hydroxypyrazole und fungizide, die diese verbindungen enthalten

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5776965A (en) * 1994-03-15 1998-07-07 Korea Research Institute Of Chemical Technology Propenoic ester derivatives having 4-hydroxypyrazole group and the use thereof
WO1995025095A1 (fr) * 1994-03-15 1995-09-21 Korea Research Institute Of Chemical Technology Derives d'ester propenoique possedant un groupe 4-hydroxypyrazole, et application
EP1110453A1 (fr) * 1995-05-24 2001-06-27 Basf Aktiengesellschaft Esters d'acide triazolyloxybenzyl-alcoxyacrylique, leur procédé de fabrication et leur utilisation
WO1996037477A1 (fr) * 1995-05-24 1996-11-28 Basf Aktiengesellschaft Esters d'acide azolyloxybenzyl-alcoxyacrylique, leur procede de fabrication et leur utilisation
CN1069638C (zh) * 1995-05-24 2001-08-15 巴斯福股份公司 唑基氧基苄基烷氧基丙烯酸酯、其制备和应用
US5935986A (en) * 1995-05-24 1999-08-10 Basf Aktiengesellschaft Azolyl oxybenzyl alkoxyacrylic acid esters, process for producing them and their use
AU712768B2 (en) * 1995-05-24 1999-11-18 Basf Aktiengesellschaft Azolyloxybenzylalkoxyacrylic esters, their preparation and their use
WO1999033812A1 (fr) * 1997-12-29 1999-07-08 Aventis Cropscience S.A. Derives 3-(5)-benzyloxypyrazole utiles comme fongicides
FR2773155A1 (fr) * 1997-12-29 1999-07-02 Rhone Poulenc Agrochimie Nouveaux composes fongicides
WO2001044238A1 (fr) * 1999-12-13 2001-06-21 Bayer Aktiengesellschaft Benzylethers de pyrazolyle
WO2001046153A1 (fr) * 1999-12-20 2001-06-28 Bayer Aktiengesellschaft Derives ethers pyrazolylbenzyliques comportant un groupe fluoromethoxy et leur utilisation comme parasiticide
US6562856B1 (en) 1999-12-20 2003-05-13 Bayer Aktiengesellschaft Pyrazolyl benzyl ether deriviatives having a fluoromethoxy group and the use thereof as pesticides
WO2015016335A1 (fr) * 2013-07-31 2015-02-05 住友化学株式会社 Composé tétrazolinone et son utilisation
CN105408322A (zh) * 2013-07-31 2016-03-16 住友化学株式会社 四唑啉酮化合物及其用途
JPWO2015016335A1 (ja) * 2013-07-31 2017-03-02 住友化学株式会社 テトラゾリノン化合物及びその用途
EP3029038A4 (fr) * 2013-07-31 2017-03-08 Sumitomo Chemical Company Limited Composé tétrazolinone et son utilisation
US9781933B2 (en) 2013-07-31 2017-10-10 Sumitomo Chemical Company, Limited Tetrazolinone compound and use thereof
CN105408322B (zh) * 2013-07-31 2019-04-19 住友化学株式会社 四唑啉酮化合物及其用途
WO2015041360A1 (fr) * 2013-09-20 2015-03-26 住友化学株式会社 Composé de tétrazolinone et son utilisation

Also Published As

Publication number Publication date
KR940000432A (ko) 1994-01-03
AU5418794A (en) 1994-01-24
KR950006150B1 (ko) 1995-06-09

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