WO2008084952A1 - 2-phenyl-4h-chromen-4-one and the use thereof as nematicide - Google Patents

2-phenyl-4h-chromen-4-one and the use thereof as nematicide Download PDF

Info

Publication number
WO2008084952A1
WO2008084952A1 PCT/KR2008/000094 KR2008000094W WO2008084952A1 WO 2008084952 A1 WO2008084952 A1 WO 2008084952A1 KR 2008000094 W KR2008000094 W KR 2008000094W WO 2008084952 A1 WO2008084952 A1 WO 2008084952A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
nematicide
chromen
phenyl
chemical formula
Prior art date
Application number
PCT/KR2008/000094
Other languages
French (fr)
Inventor
Yhong Hee Shim
Young Ki Paik
Yoong Ho Lim
Original Assignee
Konkuk University Industrial Cooperation Corp.
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 Konkuk University Industrial Cooperation Corp. filed Critical Konkuk University Industrial Cooperation Corp.
Publication of WO2008084952A1 publication Critical patent/WO2008084952A1/en

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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
    • C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only

Definitions

  • the present invention relates to a nematicide for the control of Bursaphelenchus xylophilus comprising a compound represented by Chemical Formula 1, below, or a pharmaceutically acceptable salt thereof as an effective ingredient, and the use of the compound as a nematicide.
  • pinewood nematode Bursaphelenchus xylophilus
  • Pine wilt disease is so difficult to treat that it is called the AIDS of pine trees.
  • the pinetree nematode was identified for the first time in Pusan in 1988 and .spread to Chungbuk province within ten years.
  • the nematode is transported to pine trees by pine sawyer .beetles (Monochaims alternatus) . Once infected, 99.9% of the tree wilts and dies within one year. Since the pine wilt disease first occurred in Japan and United States in the early twentieth century, increased international trade resulted in the widespread distribution of the nematode throughout the world.
  • Affected pine trees have decreased density, thereby limiting their usefulness as wood.
  • the pinewood nematode (B. xylophilus) is less than 1 mm in length, and multiplies rapidly to populations of two hundred thousand within about three weeks.
  • the nematode feeds on living plant cells surrounding the resin canals of pines. This feeding interrupts the movement of water and nutrients up and down the tree, thereby drying out the tree.
  • the nematode larvae migrate into pine sawyer beetles after the beetle's larvae develop into pupae, and are transported to new trees by the pine sawyer adults.
  • FIG. 1 shows the chemical structure of 2-phenyl-4H- chromen-4-one according to the present invention.
  • FIG. 2 is a graph showing the nematicidal effect of 2- phenyl-4H-chromen-4-one according to the present invention on B. xylophilus.
  • the present invention provides a 2-phenyl-4H-chromen-4-one compound represented by Chemical Formula 1, below, which has a lethal effect on the pinewood nematode B. xylophilus.
  • the present invention provides a nematicide for killing the pinewood nematode comprising the compound of Chemical Formula 1 or a pharmaceutically acceptable salt thereof as an effective ingredient .
  • Examples of pharmaceutically acceptable salts of the compound include pharmaceutically acceptable acid addition salts, which are exemplified by inorganic salts of hydrochloric acid, sulfuric acid, phosphoric acid, etc., and organic salts of oxalic acid, fumaric acid, maleic acid, malic acid, citric acid, tartaric acid, glutamic acid, etc.
  • the present invention further provides a nematicidal composition for killing the pinewood nematode comprising the compound of Chemical Formula 1 or a pharmaceutically acceptable salt thereof as an effective ingredient.
  • the composition preferably comprises the compound or a pharmaceutically acceptable salt thereof in an effective amount of 0.1 mM in 100-150 ml.
  • the given amount of the composition may be administered once or may be divided into several doses per day.
  • the present invention still further provides a method of killing the pinewood nematode using the compound of Chemical Formula 1.
  • the 2-phenyl-4H-chromen-4-one compound was evaluated for its . effects__on embryonic and larval ..development- and germ cell proliferation of the pinewood nematode B. xylophilus.
  • the 2-phenyl-4H-chromen-4-one was dissolved in dimethyl sulfoxide (DMSO) to provide a 1 M stock solution.
  • DMSO dimethyl sulfoxide
  • the stock solution was diluted to various concentrations.
  • the diluted compound and the pinewood nematode were aliquotted into a 96- well plate.
  • the 2-phenyl-4H-chromen-4-one was added at 10, 2, 1, 0.1, 0.01 and 0.001 mM.
  • the plate was incubated at 25 ° C for 6 hrs. 20 ⁇ i samples were collected from each well, and surviving and dead nematodes were counted and compared with the initial number of inoculated nematodes.
  • the lethal concentration at 50% mortality (IC50) was estimated, and the results are given in FIG. 2.
  • the 2-phenyl-4H-chromen-4-one exhibited 100% mortality at 2 mM and 50% mortality (IC50) at 0.0982 mM (see Table 1).
  • the 2-phenyl-4H-chromen-4-one compound according to the present invention has nematicidal activity against the pinewood nematode B. xylophilus.
  • the compound is useful as a nematicide.

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)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Disclosed is a nematicide for the control of the pinewood nematode Bursaphelenchus xylophilus comprising a 2-phenyl-4H-chromen-4-one compound or a pharmaceutically acceptable salt thereof as an effective ingredient, and the use of the compound as a nematicide. The 2-phenyl-4H-chromen-4-one compound has nematicidal activity against the pinewood nematode and is thus useful as a nematicide.

Description

2 -PHENYL-4H-CHROMEN-4-ONE AND THE USE THEREOF AS NEMATICIDE
Technical Field
The present invention relates to a nematicide for the control of Bursaphelenchus xylophilus comprising a compound represented by Chemical Formula 1, below, or a pharmaceutically acceptable salt thereof as an effective ingredient, and the use of the compound as a nematicide.
[Chemical Formula 1]
Figure imgf000002_0001
Background Art
The pinewood nematode, Bursaphelenchus xylophilus, spreads throughout pine trees and multiplies rapidly, causing rapid wilting of the tree. Pine wilt disease is so difficult to treat that it is called the AIDS of pine trees. In Korea, the pinetree nematode was identified for the first time in Pusan in 1988 and .spread to Chungbuk province within ten years. The nematode is transported to pine trees by pine sawyer .beetles (Monochaims alternatus) . Once infected, 99.9% of the tree wilts and dies within one year. Since the pine wilt disease first occurred in Japan and United States in the early twentieth century, increased international trade resulted in the widespread distribution of the nematode throughout the world. Affected pine trees have decreased density, thereby limiting their usefulness as wood.
The pinewood nematode (B. xylophilus) is less than 1 mm in length, and multiplies rapidly to populations of two hundred thousand within about three weeks. The nematode feeds on living plant cells surrounding the resin canals of pines. This feeding interrupts the movement of water and nutrients up and down the tree, thereby drying out the tree. Inside the tree, the nematode larvae migrate into pine sawyer beetles after the beetle's larvae develop into pupae, and are transported to new trees by the pine sawyer adults.
The currently available nematicide against the pinewood nematode, metasodium, is difficult to use in practice because it is expensive, and is difficult to inject into pine trees. Thus, there remains a need for the development of a novel nematicide for the control of the pinewood nematode.
Based on this background, the inventors of this application conducted intensive and thorough research in order to develop a nematicide capable of protecting pine trees from the pinewood nematode. This research resulted in the. finding. that 2-phenyl-4H-chromen-4-one effectively kills the pinewood nematode by inhibiting embryonic and larval development and germ cell proliferation during the life cycle of the nematode, thereby leading to the present invention.
Disclosure of the Invention
It is therefore a major object of the present invention to provide a 2-phenyl-4H-chromen-4-one compound, which has a lethal effect on the pinewood nematode B. xylophilus. It is another object of the present invention to provide a nematicide for killing the pinewood nematode comprising the compound as an effective ingredient.
It is a further object of the present invention to provide a nematicidal composition for killing the pinewood nematode comprising the compound as an effective ingredient.
It is yet another object of the present invention to provide the use of the 2-phenyl-4H-chromen-4-one compound as a nematicide for killing the pinewood nematode.
Brief Description of the Drawings
The above and other objects, features and other advantages of the present invention will be more clearly understood from the following detailed description taken in conjunction with the accompanying drawings, in which: FIG. 1 shows the chemical structure of 2-phenyl-4H- chromen-4-one according to the present invention; and
FIG. 2 is a graph showing the nematicidal effect of 2- phenyl-4H-chromen-4-one according to the present invention on B. xylophilus.
Best Mode for Carrying Out the Invention
In order to accomplish the above objects, the present invention provides a 2-phenyl-4H-chromen-4-one compound represented by Chemical Formula 1, below, which has a lethal effect on the pinewood nematode B. xylophilus.
[Chemical Formula 1]
Figure imgf000005_0001
In addition, the present invention provides a nematicide for killing the pinewood nematode comprising the compound of Chemical Formula 1 or a pharmaceutically acceptable salt thereof as an effective ingredient .
Examples of pharmaceutically acceptable salts of the compound include pharmaceutically acceptable acid addition salts, which are exemplified by inorganic salts of hydrochloric acid, sulfuric acid, phosphoric acid, etc., and organic salts of oxalic acid, fumaric acid, maleic acid, malic acid, citric acid, tartaric acid, glutamic acid, etc. The present invention further provides a nematicidal composition for killing the pinewood nematode comprising the compound of Chemical Formula 1 or a pharmaceutically acceptable salt thereof as an effective ingredient.
The composition preferably comprises the compound or a pharmaceutically acceptable salt thereof in an effective amount of 0.1 mM in 100-150 ml. The given amount of the composition may be administered once or may be divided into several doses per day.
The present invention still further provides a method of killing the pinewood nematode using the compound of Chemical Formula 1.
A better understanding of the present invention may be obtained through the following example, which is set forth to illustrate, but is not to be construed as the limit of the present invention.
EXAMPLE: Evaluation of the nematicidal activity of the compound against B. xylophilus
The 2-phenyl-4H-chromen-4-one compound was evaluated for its. effects__on embryonic and larval ..development- and germ cell proliferation of the pinewood nematode B. xylophilus.
The 2-phenyl-4H-chromen-4-one was dissolved in dimethyl sulfoxide (DMSO) to provide a 1 M stock solution. The stock solution was diluted to various concentrations. The diluted compound and the pinewood nematode were aliquotted into a 96- well plate.
The 2-phenyl-4H-chromen-4-one was added at 10, 2, 1, 0.1, 0.01 and 0.001 mM. The plate was incubated at 25°C for 6 hrs. 20 μi samples were collected from each well, and surviving and dead nematodes were counted and compared with the initial number of inoculated nematodes. The lethal concentration at 50% mortality (IC50) was estimated, and the results are given in FIG. 2.
As shown in FIG. 2, the 2-phenyl-4H-chromen-4-one exhibited 100% mortality at 2 mM and 50% mortality (IC50) at 0.0982 mM (see Table 1).
These results indicate that the 2-phenyl-4H-chromen-4- one has excellent nematicidal activity against the pinewood nematode B. xylophilus.
[TABLE 1]
IC50 value of the compound against B. xylophilus
Figure imgf000007_0001
Industrial Applicability As described hereinbefore, the 2-phenyl-4H-chromen-4-one compound according to the present invention has nematicidal activity against the pinewood nematode B. xylophilus. Thus, the compound is useful as a nematicide.

Claims

Claims
1. A nematicide for control of a pinewood nematode Bursaphelenchus xylophilus comprising a compound represented by Chemical Formula 1, below, or a pharmaceutically acceptable salt thereof as an effective ingredient.
[Chemical Formula 1]
Figure imgf000009_0001
2. A nematicidal compound for control of a pinewood nematode Bursaphelenchus xylophilus comprising a compound represented by Chemical Formula 1, below, or a pharmaceutically acceptable salt thereof as an effective ingredient .
[Chemical Formula 1]
Figure imgf000009_0002
3. A method of controlling a pinewood nematode Bursaphelenchus xylophilus using a compound represented by- Chemical Formula 1, below.
[Chemical Formula 1]
Figure imgf000010_0001
PCT/KR2008/000094 2007-01-12 2008-01-08 2-phenyl-4h-chromen-4-one and the use thereof as nematicide WO2008084952A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2007-0003555 2007-01-12
KR1020070003555A KR100781191B1 (en) 2007-01-12 2007-01-12 2-phenyl-4h-chromen-4-one and their use as nematocides

Publications (1)

Publication Number Publication Date
WO2008084952A1 true WO2008084952A1 (en) 2008-07-17

Family

ID=39081487

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2008/000094 WO2008084952A1 (en) 2007-01-12 2008-01-08 2-phenyl-4h-chromen-4-one and the use thereof as nematicide

Country Status (2)

Country Link
KR (1) KR100781191B1 (en)
WO (1) WO2008084952A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024094575A1 (en) * 2022-10-31 2024-05-10 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08193078A (en) * 1995-01-12 1996-07-30 Hokko Chem Ind Co Ltd Chromone derivative and agricultural and horticultural germicide
KR20000018305A (en) * 1998-09-01 2000-04-06 성재갑 Chromene derivative useful for a cdk inhibitor
JP2006069906A (en) * 2004-08-31 2006-03-16 Sumitomo Chemical Co Ltd Chromone compound and its use

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08225409A (en) * 1995-02-21 1996-09-03 Kobe Steel Ltd Agent and coating for controlling attachment of underwater organism
JPH11116564A (en) 1997-10-09 1999-04-27 Otsuka Chem Co Ltd Chromone derivative

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08193078A (en) * 1995-01-12 1996-07-30 Hokko Chem Ind Co Ltd Chromone derivative and agricultural and horticultural germicide
KR20000018305A (en) * 1998-09-01 2000-04-06 성재갑 Chromene derivative useful for a cdk inhibitor
JP2006069906A (en) * 2004-08-31 2006-03-16 Sumitomo Chemical Co Ltd Chromone compound and its use

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024094575A1 (en) * 2022-10-31 2024-05-10 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents

Also Published As

Publication number Publication date
KR100781191B1 (en) 2007-11-30

Similar Documents

Publication Publication Date Title
UA98315C2 (en) Insecticide composition, a method for treating farm crops and the use of the composition
MX2014013430A (en) Substituted pyrazole-containing compounds and their use as pesticides.
EA200970627A1 (en) PESTICIDE COMPOSITION INCLUDING DERIVATIVE 2-Pyridylmethylbenzamide and Insecticidal Compound
US20210015094A1 (en) Application of methylmalonic acid in the preparation of nematode insecticides
EA200970564A1 (en) PESTICIDAL COMPOSITION CONTAINING A SYNTHETIC COMPOUND USEFUL AS A AGENT OF THE FORMATION OF CLUB BEAN PLANTS AND FUNGICIDE COMPOUND
Kim et al. Identification and biological characteristics of an antifungal compound extracted from Cocklebur (Xanthium Strumarium) against Phytophthora drechsleri
Rajmohan et al. Studies on the insecticidal properties of Chromolaena odorata (Asteraceae) against the life cycle of the mosquito, Aedes aegypti (Diptera: culicidae
Hu et al. In vitro screening of fungicidal chemicals for antifungal activity against Saprolegnia
WO2008084952A1 (en) 2-phenyl-4h-chromen-4-one and the use thereof as nematicide
CN102100234A (en) Sterilization composition containing pyraclostrobin and carbamates
CN103651504A (en) Compound insecticide containing dinotefuran and pymetrozine
Al-Sayed et al. Meloidogyne incognita and tomato response to thiamine, ascorbic acid, L-arginine, and L-glutamic acid
EP0251014A2 (en) 2-Trifluoromethyl benzimidazoles
Bi-Zhen et al. Molt disruption and mortality of Locusta migratoria var. manilensis (Meyen)(Orthoptera: Acrididae) caused by insect growth regulators
CN101965841A (en) Application of 4-tertiary butyl-5-(1,2,4-triazole-1-base)-2-benzyliminothiazole in preparation of insecticide
Jin et al. The role of chasmothecia in the initiation of epidemics of powdery mildew (Podosphaera aphanis) and the role of silicon in controlling the epidemics on strawberry
Martinez-Tomas et al. Effects of an aqueous extract of Azadirachta indica on the growth of larvae and development of pupae of Culex quinquefasciatus
Shin et al. Efficacy of fluopicolide against Phytophthora capsici causing pepper Phytophthora blight
Jurc et al. Dasineura gleditchiae (Osten Sacken, 1866)(Diptera: Cecidomyiidae), honeylocust pod gall midge: a new invasive species in Slovenia
Csinos et al. Tomato spotted wilt virus severity influenced by acibenzolar-s-methyl, imidacloprid and age of tobacco transplants
CN107467019B (en) Application of 2-octanone in preparing medicine for inhibiting nematode activity
Surapwar et al. Effect of different bed disinfectants on economic traits of double hybrid mulberry silkworm (Bombyx mori L.)
Marzouk et al. EFFECTS OF THREE PESTICIDES ON SOME BIOLOGICAL ASPECTS OF COTTON LEAF WORM (Spodoptera littoralis, BOISD) LARVAE UNDER LABORATORY CONDITIONS.
Kozik et al. Synthesis and fungistatic activity of aryl-substituted naphthalene-and indene-2-carbonitriles
WO2012062749A1 (en) Benzimidazolidinones that can be used as fungicides

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 08704634

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 08704634

Country of ref document: EP

Kind code of ref document: A1