[go: up one dir, main page]

WO2000056152A1 - Utilisation aux fins de protection des gaulis de resineux - Google Patents

Utilisation aux fins de protection des gaulis de resineux Download PDF

Info

Publication number
WO2000056152A1
WO2000056152A1 PCT/SE2000/000580 SE0000580W WO0056152A1 WO 2000056152 A1 WO2000056152 A1 WO 2000056152A1 SE 0000580 W SE0000580 W SE 0000580W WO 0056152 A1 WO0056152 A1 WO 0056152A1
Authority
WO
WIPO (PCT)
Prior art keywords
hydroxy
group
optionally substituted
methyl
alkoxy groups
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.)
Ceased
Application number
PCT/SE2000/000580
Other languages
English (en)
Inventor
Göran Nordlander
Henrik Nordenhem
Anna-Karin Borg-Karlson
Rikard Unelius
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.)
Robigus AB
Original Assignee
Robigus AB
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 Robigus AB filed Critical Robigus AB
Priority to CA002365998A priority Critical patent/CA2365998A1/fr
Priority to AU41587/00A priority patent/AU4158700A/en
Priority to EP00921251A priority patent/EP1162885A1/fr
Priority to PL00351381A priority patent/PL351381A1/xx
Publication of WO2000056152A1 publication Critical patent/WO2000056152A1/fr
Priority to NO20014590A priority patent/NO20014590L/no
Anticipated expiration legal-status Critical
Ceased 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/48—Nitro-carboxylic acids; Derivatives thereof
    • 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
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
    • A01N31/16—Oxygen or sulfur directly attached to an aromatic ring system with two or more oxygen or sulfur atoms directly attached to the same aromatic ring system
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
    • 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
    • A01N43/24—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 two or more hetero atoms
    • A01N43/26—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 two or more hetero atoms five-membered rings
    • A01N43/28—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 two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3

Definitions

  • the present invention relates to the use of at least one compound for conifer sapling protection. It also relates to the use of a composition for conifer sapling protection.
  • the pine weevil is, therefore, one of the economically most important insects in Sweden.
  • the species is known as a serious noxious insect in large parts of Europe and Asia. In North America there are some closely related species with a similar way of living (Hylobius pales, Hylobius congener, and Pachylobhis picivorus).
  • the present invention relates to the use of at least one compound for conifer sapling protection. It also relates to the use of a composition for conifer sapling protection. Detailed description of the invention
  • One object of the present invention is the use of at least one compound for conifer sapling protection, characterised in that the compounds are selected from the fol- lowing compounds with Formula I:
  • Ri, R 2 , R 3 , R 4 , and R 5 each independently stand for
  • C ⁇ -C ⁇ 2 -alkyl group preferably a C ⁇ -C 8 -alkyl group, more preferably a C ⁇ -C 6 - alkyl group, optionally substituted with one or more halogen, hydroxy or -C 12 alkoxy groups, preferably Cp -alkoxy groups, more preferably C C 6 -alkoxy groups; most preferably wherein the C ⁇ -C ⁇ 2 -alkyl group is a methyl group;
  • C ⁇ -C ⁇ -alkoxy group preferably a C C 8 -alkoxy group, optionally substituted with one or more halogen, hydroxy or C ⁇ -C ⁇ -alkoxy groups, preferably Cj-C 8 - alkoxy groups, more preferably Ci-C ⁇ -alkoxy groups; most preferably wherein the C ⁇ -C ⁇ 2 -alkoxy group is a methoxy, piperonyl or n-octyloxy group,
  • - halogen preferably chloro or bromo
  • R' stands for - a C ⁇ -C ⁇ 2 -alkyl group, preferably a C ⁇ -C 8 -alkyl group, more preferably a C[-C 6 - alkyl group, optionally substituted with one or more halogen, hydroxy or C ⁇ -C ⁇ 2 - alkoxy groups, preferably C C 8 -alkoxy groups, more preferably C ⁇ -C 6 -alkoxy groups, most preferably wherein the CrC ⁇ 2 -alkyl group is a 1-propenyl or a 2- propenyl group;
  • - a hydroxy substituted C ⁇ -C !2 -hydrocarbon group preferably a hydroxy substituted CrC ⁇ -hydrocarbon group, more preferably a hydroxy substituted C C 3 - hydrocarbon group, most preferably a hydroxymethyl or a 3 -hydroxy -n-propyl group;
  • - a methylcarboxylic group preferably a methylcarboxylic acid or a methylcar- boxylic Ci-C 6 -ester group, more preferably a methylcarboxylic acid group; or
  • C ⁇ -C ⁇ -alkyl group optionally substituted with one or more deuterium, halogen, hydroxy, aryl, optionally substituted with one or more C i -C h alky 1 groups, preferably C ⁇ -C -alkyl groups, more preferably C ⁇ -C 6 -alkyl groups, C C ⁇ 2 -alkoxy groups, preferably C C 8 -alkoxy groups, more pref- erably -C ⁇ -alkoxy groups, or C ⁇ -C ⁇ 2 -alkoxy groups, preferably C C 8 - alkoxy groups, more preferably CpC 6 -alkoxy groups, most preferably wherein the C ⁇ -C ⁇ -alkyl group is a methyl, ethyl, trideuteriomethyl, 2,2,2- rrifluoroethyl, isopropyl, 3-(3,4-dimethoxyphenyl)-n-propyl, (E)-3-n-n-
  • Ri, R , R , R- ! , R 5 , and R ' are as defined above, pure or in a solvent, with or without a suitable carrier such as wood, cellulose, wood-flour, straw, cork, cane, lignin, lig- nocellulose, rubber, gum, leather or skin, milled carbon, fats or waxes of animal, vegetable, or synthetic origin, natural resins of animal or vegetable origin, plastic, organic polymers such as polyvinyl acetate, polyaciylates, polyvinyl chloride, chlorinated polyethylene, polyols such as polyethylene glycol, synthetic or natural latexes, silicone polymers or resins, silicates, pumice, silica, or any mixture thereof.
  • a suitable carrier such as wood, cellulose, wood-flour, straw, cork, cane, lignin, lig- nocellulose, rubber, gum, leather or skin, milled carbon, fats or waxes of animal, vegetable, or synthetic origin, natural
  • a suitable solvent is selected from the group consisting of Ci-C ⁇ -alkohols and C C C ⁇ -alkyl esters of C ⁇ -C 6 -alkanoic acids, preferably methyl acetate, methanol, and isopropanol.
  • C ⁇ -C ⁇ -alkyl refers to a saturated or unsaturated, straight or branched chained alkyl radical containing from 1 to 12 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, 1-propenyl, 2-propenyl, n-butyl, isobutyl, t-butyl, 1- butenyl, 2-butenyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n- undecyl, n-dodecyl etc;
  • C ⁇ -C ⁇ 2 -alkyr all subgroups thereof are contemplated such as d-Cn-alkyl, C,-C ⁇ 0 -alkyl, C,-C 9 -alkyl, C r C 8 -alkyl, C C 7 -alkyl, C,-C 6 -alkyl, C ⁇ -C 5 -alkyl, C C -alkyl, C C 3 -alkyl, C ⁇ -C 2 -alkyl, etc; b) the term “halogen” refers to a fluoro, chloro, bromo or iodo group; c) the term "C ⁇ -C ⁇ 2 -alkoxy” refers to a saturated or unsaturated, straight or branched chained alkoxy radical containing from 1 to 12 carbon atoms, such as methoxy, ethoxy, ethenoxy, n-propoxy, isopropoxy, 1-n-propenoxy, n
  • C ⁇ -C ⁇ 2 -alkoxy For parts of the range "C ⁇ -C ⁇ 2 -alkoxy" all subgroups thereof are contemplated such as Ci-C i i -alkoxy, CpCio-alkoxy, -Cg-alkoxy, Cj-C 8 -alkoxy, C ⁇ -C 7 - alkoxy, C ⁇ -C 6 -alkoxy, -Cs-alkoxy, C ⁇ -C -alkoxy, C C 3 -alkoxy, C C -alkoxy, etc; d) the term "hydroxy substituted CpC ⁇ 2 -hydrocarbon group” refers to a saturated or unsaturated, straight or branched acyclic hydrocarbon radical containing one or more hydroxyl groups and containing 1 to 12 carbon atoms, such as hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxy-n-propyl, 2-hydroxy-n- propyl, 3-hydroxy-n-propyl,
  • C C ⁇ 2 -hydrocarbon For parts of the range "C C ⁇ 2 -hydrocarbon” all subgroups thereof are contemplated such as CpC ii -hydrocarbon, C C ⁇ o-hydrocarbon, Ci-Cg-hydrocarbon, C C 8 -hydrocarbon, C ⁇ -C 7 -hydrocarbon, C C 6 -hydrocarbon, C ⁇ -C 5 -hydrocarbon, C ⁇ -C 4 -hydrocarbon, C C 3 -hydrocarbon, C C 2 -hydrocarbon, etc; e) the term “methylcarboxylic group” refers to a methylcarboxylic acid, a methylcarboxylic C ⁇ -C 6 -ester or a methylcarboxylic C 0 -C 6 -amide group; f) the term " methylcarboxylic Ci-C 6 -ester” refers to a saturated or unsaturated, straight or branched alkyl ester of a methylcarboxylic acid group
  • isotopes all compounds with naturally occur- ring isotopes such as all possible deuterium and 13 C-isotopes of the compounds according to the invention.
  • esters and salts of the compounds according to the in- vention are included within the scope of the invention.
  • esters of the compounds are intended e.g. methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl and n-pentyl esters.
  • salts of the compounds are intended in particular environmentally acceptable acid and base addition salts.
  • environmentally acceptable acid addition salts are intended to be any non-toxic organic or inorganic acid addition salt of the base compounds with the formula I.
  • suitable inorganic acids hydrochloric acid, hydrobromic acid, sulphuric acid, phosphoric acid and acid metal salts such as sodium monohydrogen ortophosphate and potassium hydrogensul- phate.
  • illustrative organic acids that form suitable salts are mono-, di- and tricarboxylic acids.
  • acids examples include acetic acid, glycolic acid, lactic acid, pyruvic acid, malonic acid, succinic acid, glutaric acid, fumaric acid, malic acid, tartaric acid, citric acid, ascorbic acid, maleic acid, hydroxymaleic acid, ben- zoic acid, hydroxybenzoic acid, phenylacetic acid, cinnamic acid, salicylic acid, 2- phenoxybenzoic acid, and sulphonic acids such as p-toluenesulphonic acid, methanesulphonic acid and 2-hydroxyethanesulphonic acid.
  • Such salts could either be in hydrated or anhydrous form.
  • the acid addition salts of these compounds are generally water soluble and different hydrophilic organic solvents and, that compared to the free base forms thereof, generally display higher melting points.
  • environmentally acceptable base salts are intended to be any non- toxic organic or inorganic base addition salt of the base compounds with the formula I.
  • suitable inorganic bases that form suitable salts are alkali and earth alkali metal hydroxides and carbonates such as sodium hydroxide, sodium carbonate, potassium hydroxide, potassium carbonate, calcium hydroxide, calcium carbonate, magnesium hydroxide, magnesium carbonate and ammonia.
  • illustrative organic bases that form suitable salts are methylamine, dimethylamine, trimethylamine and picoline. Either mono- or dibasic salts could be formed with such compounds.
  • the base addition salts of these compounds are generally water soluble and different hydrophilic organic solvents and, that compared to the free base forms thereof, generally display higher melting points.
  • Homovanillic acid 4 3 -(4-hydroxy-3 -methoxyphenyl )- 1 -propanol
  • Another object of the present invention relates to the use for conifer sapling protection against insects, characterised in that the insect species belong to the beetle (Coleoptera) family Curculionidae (including subfamilies Curculioninae and Scoly- tinae), particularly species of the genera Hylobius, Pachylobius and Hylastes, spe- cifically the species Hylobius abietis, Hylobius pmastri, Hylobius pales, Hylobius congener, Pachylobius pictvorus, Hylastes brunneus and Hylastes cuniculanus.
  • the insect species belong to the beetle (Coleoptera) family Curculionidae (including subfamilies Curculioninae and Scoly- tinae), particularly species of the genera Hylobius, Pachylobius and Hylastes, spe- cifically the species Hylobius abietis, Hylobius pmastr
  • Injections were made in a splitless mode for 30 seconds at 200°C using helium as the carrier gas.
  • the instrument was equipped with a DB-5 fused silica capillary column (J&W 30 m, i.d. 0.25 mm, film thickness 0.25 ⁇ m)
  • the insects used for the experiments was the pine weevil (Hylobius abietis) taken from their natural environment, i e coniferous forests.
  • Preparation of gnawing-inhibiting compositions are prepared by incorporating the compounds in a suitable matrix. When the compounds are not soluble in the matrix a solvent such as methanol or isopropanol is used to transfer the compounds into the matrix. At most 0.5 g per sapling of the compounds is needed. A used ratio is 40 g compound, 20 g carrier e.g. a polyol, and 80 ml of a solvent.
  • the compounds 5, 11, 13, 14, 15, 18, 19, 20, 21, 22, 31, 32, 33, 35, 39, 50, 52, 53, and 64 could be purchased from the Sigma-Aldrich Sweden AB, Solk- raftsv. 14c, 135 70 Swiss, Sweden.
  • the compounds 3, 10, 12, 49, 51, 60, 61, 62, 63, 70, 71, 72, 73, 80, 81, and 82 could be purchased from Lancaster Synthesis Ltd, Eastgate, White Lund, Morecambe, Lancashire LA3 3DY, UK.
  • n-dodecanol (3.84 mmol) was added to a stirred solution of dicyclohexylcarbodi- imide (1.19 g, 5.77 mmol), 4-(dimethylamino)pyridine (0.038 g, 0.31 mmol) and 3,5-dimethoxybenzoic acid (5.77 mmol) in dry CH 2 CI 2 (8.5 ml) (Kato 1985).
  • the mixture was stirred at room temperature for 12 h, and then diluted with hexane (2 ml).
  • the mixture was filtered and the solid material was washed with CH 2 C1 2 .
  • the combined filtrate and washings were concentrated in vacuo and then subjected to silica gel chromatography. n-dodecyl 3,4-dimethoxybenzoate was analysed by NMR and mass spectroscopy.
  • 3,5-dimethoxybenzoyl chloride was sti ⁇ ed with excess ethylamine solution (70 % in water) for 3 days, and then partitioned between water and ethyl acetate. MPLC of the ethyl acetate layer gave ethyl 3,5-dimethoxybenzamide.
  • Ethanethiol (3.84 mmol) was added to a sti ⁇ ed solution of dicyclohexyl- carbodiimide (1.19 g, 5.77 mmol), 4-(dimethylamino)pyridine (0.038 g, 0.31 mmol) and 3,5-dimethoxybenzoic acid (5.77 mmol) in dry CH 2 CI 2 (8.5 ml) (Kato 1985).
  • the mixture was sti ⁇ ed at room temperature for 12 h, and then diluted with hexane (2 ml).
  • the mixture was filtered and the solid material was washed with CH 2 C1 2 .
  • the combined filtrate and washings were concentrated in vacuo and then subjected to silica gel chroma- tography. Ethylthionyl 3,5-dimethoxybenzoate was analysed by NMR and mass spectroscopy.
  • Trideuteriomethanol (3.84 mmol) was added to a sti ⁇ ed solution of dicyclohexyl- carbodiimide (1.19 g, 5.77 mmol), 4-(dimethylamino)pyridine (0.038 g, 0.31 mmol) and 3,5-dimethoxybenzoic acid (5.77 mmol) in dry CH 2 CI 2 (8.5 ml) (Kato 1985).
  • the mixture was sti ⁇ ed at room temperature for 12 h, and then diluted with hexane (2 ml). The mixture was filtered and the solid material was washed with CH 2 C1 .
  • Example 2 Test of gnawing-inhibiting effect of substances applied on pine bark.
  • the substance with the strongest repellent effect in the laboratory test has also been tested in field experiments by applying it in a matrix brushed on the saplings before plating.
  • the substance (40 g) was mixed with Bol- torn H40 ® (a dendritic polymer (a polyol) from Perstorp AB, SE-284 80, Sweden, CAS no. 150 504-00-0; 20 g) and isopropanol (80 ml). This mixture was used for 75 saplings.
  • This treatment significantly reduced the extent of gnawing on saplings, and the effect was so strong that it definitely should be useful for practical protec- 27 tion from pine weevil damage (Table 2). The effect seems considerably stronger compared to earlier field testing gnawing-inhibiting agents against the pine weevil (Eidmann 1984, Schlyter 1998).

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne l'utilisation d'au moins un composé de la formule (I), aux fins de protection des gaulis de résineux. L'invention concerne également l'utilisation d'une composition destinée à la protection des gaulis de résineux.
PCT/SE2000/000580 1999-03-23 2000-03-23 Utilisation aux fins de protection des gaulis de resineux Ceased WO2000056152A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
CA002365998A CA2365998A1 (fr) 1999-03-23 2000-03-23 Utilisation aux fins de protection des gaulis de resineux
AU41587/00A AU4158700A (en) 1999-03-23 2000-03-23 Use for conifer sapling protection
EP00921251A EP1162885A1 (fr) 1999-03-23 2000-03-23 Utilisation aux fins de protection des gaulis de resineux
PL00351381A PL351381A1 (en) 1999-03-23 2000-03-23 Use for conifer sapling protection
NO20014590A NO20014590L (no) 1999-03-23 2001-09-21 Anvendelse for beskyttelse av unge nåletr¶r

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SE9901062A SE515989C2 (sv) 1999-03-23 1999-03-23 Användning av vissa föreningar för skydd av barrträdsplantor mot insektsarterna Hylobius abietis, Hylobius pinastri, Hylobius pales, Hylobius congener och Pachylobius picivorus
SE9901062-1 1999-03-23

Publications (1)

Publication Number Publication Date
WO2000056152A1 true WO2000056152A1 (fr) 2000-09-28

Family

ID=20414973

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/SE2000/000580 Ceased WO2000056152A1 (fr) 1999-03-23 2000-03-23 Utilisation aux fins de protection des gaulis de resineux

Country Status (7)

Country Link
EP (1) EP1162885A1 (fr)
AU (1) AU4158700A (fr)
CA (1) CA2365998A1 (fr)
NO (1) NO20014590L (fr)
PL (1) PL351381A1 (fr)
SE (1) SE515989C2 (fr)
WO (1) WO2000056152A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002000022A1 (fr) * 2000-06-26 2002-01-03 Forskarpatent I Syd Composition pour empecher des charançons de s'alimenter
WO2002015691A1 (fr) * 2000-08-25 2002-02-28 Robigus Ab Utilisation pour la protection des gaulis coniferes contre les degats causes par les insectes
EP3127891A4 (fr) * 2014-03-31 2017-04-05 Medina Esquer, Luis Román Extraits de cascarilles agricoles efficaces pour modifier le métabolisme de plantes
WO2023139053A1 (fr) * 2022-01-19 2023-07-27 Firmenich Sa Compositions de lutte contre les arthropodes

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE696347C (de) * 1937-02-20 1940-09-19 I G Farbenindustrie Akt Ges Insektenbekaempfung
US4219570A (en) * 1978-02-20 1980-08-26 Ajinomoto Company, Incorporated Insect repellents and a method of repelling insects
JPS56115206A (en) * 1980-02-15 1981-09-10 Yoshitomi Pharmaceutical Protective agent for damage due to eating by limnoria japonica richardson
US5403863A (en) * 1993-08-31 1995-04-04 The United States Of America As Represented By The Secretary Of Agriculture Scolytid repellant
US5518757A (en) * 1993-08-31 1996-05-21 The United States Of America As Represented By The Department Of Agriculture 4-allylanisole analog scolytid repellents
US5695807A (en) * 1993-08-31 1997-12-09 The United States Of America As Represented By The Secretary Of Agriculture 4-allylanisole analog scolytid repellents
WO1998053678A2 (fr) * 1997-05-30 1998-12-03 Octrooibureau Kisch N. V. Moyen et procede de protection phytosanitaire
US6051612A (en) * 1996-12-09 2000-04-18 Simon Fraser University Non-host volatiles as repellents for conifer-infesting bark beetles

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE696347C (de) * 1937-02-20 1940-09-19 I G Farbenindustrie Akt Ges Insektenbekaempfung
US4219570A (en) * 1978-02-20 1980-08-26 Ajinomoto Company, Incorporated Insect repellents and a method of repelling insects
JPS56115206A (en) * 1980-02-15 1981-09-10 Yoshitomi Pharmaceutical Protective agent for damage due to eating by limnoria japonica richardson
US5403863A (en) * 1993-08-31 1995-04-04 The United States Of America As Represented By The Secretary Of Agriculture Scolytid repellant
US5518757A (en) * 1993-08-31 1996-05-21 The United States Of America As Represented By The Department Of Agriculture 4-allylanisole analog scolytid repellents
US5695807A (en) * 1993-08-31 1997-12-09 The United States Of America As Represented By The Secretary Of Agriculture 4-allylanisole analog scolytid repellents
US6051612A (en) * 1996-12-09 2000-04-18 Simon Fraser University Non-host volatiles as repellents for conifer-infesting bark beetles
WO1998053678A2 (fr) * 1997-05-30 1998-12-03 Octrooibureau Kisch N. V. Moyen et procede de protection phytosanitaire

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 198143, Derwent World Patents Index; AN 1981-78495D, XP002948947, YOSHITOMI PHARM IND KK: "Pest control agent for Lyctus brunneus Stephens - contains N,N-di:ethyl-meta-toluamide as active component" *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002000022A1 (fr) * 2000-06-26 2002-01-03 Forskarpatent I Syd Composition pour empecher des charançons de s'alimenter
WO2002015691A1 (fr) * 2000-08-25 2002-02-28 Robigus Ab Utilisation pour la protection des gaulis coniferes contre les degats causes par les insectes
EP3127891A4 (fr) * 2014-03-31 2017-04-05 Medina Esquer, Luis Román Extraits de cascarilles agricoles efficaces pour modifier le métabolisme de plantes
WO2023139053A1 (fr) * 2022-01-19 2023-07-27 Firmenich Sa Compositions de lutte contre les arthropodes

Also Published As

Publication number Publication date
SE9901062D0 (sv) 1999-03-23
CA2365998A1 (fr) 2000-09-28
AU4158700A (en) 2000-10-09
NO20014590L (no) 2001-10-24
SE515989C2 (sv) 2001-11-05
SE9901062L (sv) 2000-09-24
EP1162885A1 (fr) 2001-12-19
PL351381A1 (en) 2003-04-07
NO20014590D0 (no) 2001-09-21

Similar Documents

Publication Publication Date Title
Hall et al. Identification of components of male-produced pheromone of coffee white stemborer, Xylotrechus quadripes
Stevenson et al. Chemical basis for resistance in sweetpotato Ipomoea batatas to the sweetpotato weevil Cylas puncticollis
US6986898B1 (en) Synergistic and residual pesticidal compositions containing plant essential oils with enzyme inhibitors
EP3488695A1 (fr) Compositions pesticides
Subchev et al. Sex pheromone of female vine bud moth, Theresimima ampellophaga comprises (2 S)-butyl (7 Z)-tetradecenoate
Rice et al. Structural requirements for monoterpenoid activity against insects
US3702864A (en) Allyl or propargyl esters of substituted alpha-phenyl phenylacetic acid
Unelius et al. Structure–activity relationships of benzoic acid derivatives as antifeedants for the pine weevil, Hylobius abietis
US9125406B2 (en) Methods and compositions for control of cabbage looper, trichoplusia ni
EP1162885A1 (fr) Utilisation aux fins de protection des gaulis de resineux
Ho et al. Identification and synthesis of the sex pheromone of the Madeira mealybug, Phenacoccus madeirensis Green
US20100160451A1 (en) METHODS AND COMPOSITIONS FOR CONTROL OF CABBAGE LOOPER, Trichoplusia ni
US4235926A (en) Insecticidal esters
CH658772A5 (fr) Compositions pesticides renfermant un photostabilisant.
Francke et al. Major sex pheromone component of female herald moth Scoliopteryx libatrix is the novel branched alkene (6Z, 13)-methylheneicosene
Månsson et al. Nonanoic acid, other alkanoic acids, and related compounds as antifeedants in Hylobius abietis pine weevils
DE2432951A1 (de) (+)-cis-chrysanthemumsaeureester und insektizide und akarizide mittel
JP2010510285A (ja) 寄生虫の駆除および阻止用組成物
US9497963B2 (en) Methods and compositions for control of gypsy moth, Lymantria dispar
EP2840897B1 (fr) Utilisation de dérivés de 1,3-benzodioxole dans des compositions insecticides
US20100297059A1 (en) Methods and compositions for control of gypsy moths, lymanria dispar
Sugie et al. A sex attractant of the cabbage webworm, Hellula undalis Fabricius (Lepidoptera: Pyralidae)
US4474755A (en) Bagworm moth attractant and plant protectant
Prestwich et al. Fluorolipids as targeted termiticides and biochemical probes
WO2002015691A1 (fr) Utilisation pour la protection des gaulis coniferes contre les degats causes par les insectes

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY CA CH CN CR CU CZ DE DK DM DZ EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT TZ UA UG US UZ VN YU ZA ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH GM KE LS MW SD SL SZ TZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
ENP Entry into the national phase

Ref document number: 2365998

Country of ref document: CA

Ref country code: CA

Ref document number: 2365998

Kind code of ref document: A

Format of ref document f/p: F

WWE Wipo information: entry into national phase

Ref document number: 2000921251

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 2000921251

Country of ref document: EP

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

WWE Wipo information: entry into national phase

Ref document number: 09937328

Country of ref document: US

NENP Non-entry into the national phase

Ref country code: JP

WWW Wipo information: withdrawn in national office

Ref document number: 2000921251

Country of ref document: EP