FR2543403A1 - NOVEL CYCLODEXTRIN INCLUSION COMPLEXES, THEIR PREPARATION AND THEIR USE AS INSECTICIDES - Google Patents
NOVEL CYCLODEXTRIN INCLUSION COMPLEXES, THEIR PREPARATION AND THEIR USE AS INSECTICIDES Download PDFInfo
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- FR2543403A1 FR2543403A1 FR8404887A FR8404887A FR2543403A1 FR 2543403 A1 FR2543403 A1 FR 2543403A1 FR 8404887 A FR8404887 A FR 8404887A FR 8404887 A FR8404887 A FR 8404887A FR 2543403 A1 FR2543403 A1 FR 2543403A1
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- inclusion complex
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
- C08B37/0015—Inclusion compounds, i.e. host-guest compounds, e.g. polyrotaxanes
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- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
- A01N25/10—Macromolecular compounds
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- 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
- A01N49/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing the group, wherein m+n>=1, both X together may also mean —Y— or a direct carbon-to-carbon bond, and the carbon atoms marked with an asterisk are not part of any ring system other than that which may be formed by the atoms X, the carbon atoms in square brackets being part of any acyclic or cyclic structure, or the group, wherein A means a carbon atom or Y, n>=0, and not more than one of these carbon atoms being a member of the same ring system, e.g. juvenile insect hormones or mimics thereof
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- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
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- Wood Science & Technology (AREA)
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- Insects & Arthropods (AREA)
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- Polymers & Plastics (AREA)
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- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
LA PRESENTE INVENTION A POUR OBJET DE NOUVEAUX COMPLEXES D'INCLUSION DE LA CYCLODEXTRINE COMPRENANT DE LA CYCLODEXTRINE ET UN REGULATEUR DE LA CROISSANCE DES INSECTES CHOISI PARMI L'HYDROPRENE, LE METHROPRENE ET LE KINOPRENE. CES COMPLEXES D'INCLUSION PEUVENT ETRE UTILISES POUR LA LUTTE CONTRE LES INSECTES.THE SUBJECT OF THE PRESENT INVENTION IS TO NEW COMPLEXES FOR INCLUDING CYCLODEXTRIN CONTAINING CYCLODEXTRIN AND AN INSECT GROWTH REGULATOR CHOSEN FROM HYDROPRENE, METHROPRENE AND KINOPRENE. THESE INCLUSION COMPLEXES MAY BE USED FOR INSECT CONTROL.
Description
La présente invention a pour objet de nouveaux complexesThe present invention relates to new complexes
d'inclusion de la cyclodextrine, leur préparation et leur utili- of inclusion of cyclodextrin, their preparation and their use
sation commme insecticides.as insecticides.
La présente invention a plus particulièrement pour objet les complexes d'inclusion de la cyclodextrine et d'un régulateur de la croissance des insectes choisi parmi l'hydroprène, le méthoprène A more particular subject of the present invention is the inclusion complexes of cyclodextrin and of an insect growth regulator chosen from hydroprene, methoprene
et le kinoprène.and kinoprene.
L'hydroprène est le ( 2 E,4 E)-3,7,11-triméthyl-2,4- The hydroprene is (2 E, 4 E) -3,7,11-trimethyl-2,4-
dodécadiénoate d'éthyle, décrit dans le brevet américain ethyl dodecadienoate, described in the US patent
n 4 021 461 Le méthoprène est le ( 2 E,4 E)-11-méthoxy-3,7,11- n 4,021,461 Methoprene is (2 E, 4 E) -11-methoxy-3,7,11-
triméthyl-2,4-dodécadiénoate d'isopropyle, décrit dans le brevet isopropyl trimethyl-2,4-dodecadienoate, described in the patent
américain no 3 904 662 Le kinoprène est le ( 2 E,4 E)-3,7,11- American No. 3,904,662 Kinoprene is (2 E, 4 E) -3,7,11-
triméthyl-2,4-dodécadiénoate de prop-2-ynyle, décrit dans ledit prop-2-ynyl trimethyl-2,4-dodecadienoate, described in said
brevet américain n 4 021 461.U.S. Patent No. 4,021,461.
Ces composés sont des insecticides connus, analogues de l'hormone juvénile, c'est-à-dire des régulateurs de la croissance des insectes (RCI) , qui perturbent la métamorphose d'insectes non adultes, provoquant un développement anormal aboutissant à la mort These compounds are known insecticides, analogues of the juvenile hormone, i.e. regulators of insect growth (RCI), which disturb the metamorphosis of non-adult insects, causing abnormal development leading to death
ou à l'inaptitude à la reproduction des insectes. or the inability to reproduce insects.
Alors que l'hydroprène, le méthoprène et le kinoprène sont des RCI actifs, on a découvert que leur activité est fortement While hydroprene, methoprene and kinoprene are active RCIs, it has been discovered that their activity is strongly
améliorée et augmentée lorsqu'ils sont associés avec la cyclo- improved and increased when combined with cyclo
dextrine pour former un complexe d'inclusion L'action du complexe est de façon surprenante supérieure à celle du RCI utilisé seul, et dextrin to form an inclusion complex The action of the complex is surprisingly superior to that of the RCI used alone, and
présente une stabilité et une efficacité fortement améliorées. exhibits greatly improved stability and efficiency.
Lorsque le complexe est inclus dans une formulation pour appât, ce dernier est bien moins repoussant aux insectes cibles et est ainsi plus efficace Le complexe d'inclusion semble fournir au RCI une stabilité chimique et une stabilité à la lumière ainsi qu'une When the complex is included in a bait formulation, the latter is much less repellent to target insects and is therefore more effective. The inclusion complex seems to provide RCI with chemical and light stability as well as
résistance h l'évaporation.resistance to evaporation.
La cyclodextrine à l'état brut peut être préparée par fermentation d'amidon de pomme de terre avec une amylase alcaline obtenue à partir d'une souche de Bacillus macerans selon le procédé décrit dans la demande de brevet japonais publiée N O 74/117 691 On peut utiliser également une enzyme fixée sur une résine pour préparer un mélange de cyclodextrines (Chem Abs 86,87657) La b-cyclodextrine pure peut être préparée à partir de dextrine d'amidon de pomme de terre douce, comme décrit dans la demande de brevet allemand N O 2 532 051, ou par K Horikoshi, dans Process Cyclodextrin in the raw state can be prepared by fermentation of potato starch with an alkaline amylase obtained from a strain of Bacillus macerans according to the method described in the published Japanese patent application NO 74/117 691 On can also use an enzyme attached to a resin to prepare a mixture of cyclodextrins (Chem Abs 86.87657) Pure b-cyclodextrin can be prepared from sweet potato starch dextrin, as described in the patent application German NO 2,532,051, or by K Horikoshi, in Process
Biochemistry 14, pages 26-28, 30 ( 1979). Biochemistry 14, pages 26-28, 30 (1979).
Les complexes d'inclusion de la présente invention peuvent être préparés par réaction d'un régulateur de la croissance des insectes choisi parmi l'hydroprène, le méthoprène et le kinoprene, avec de la cyclodextrine dans de l'eau et sous atmosphère The inclusion complexes of the present invention can be prepared by reacting an insect growth regulator chosen from hydroprene, methoprene and kinoprene, with cyclodextrin in water and under atmosphere
d'un gaz inerte.of an inert gas.
La réaction est effectuée de préférence en présence de petites quantités d'un solvant organique soluble dans l'eau capable d'augmenter la solubiité du RCI dans l'eau Comme exemple d'un tel solvant on peut citer par exemple un alcool, tel que le méthanol ou l'éthanol, et l'acétone De préférence, la quantité de solvant organique ne doit pas dépasser 50 % en poids de l'eau utilisée pour The reaction is preferably carried out in the presence of small amounts of a water-soluble organic solvent capable of increasing the solubiity of RCI in water. As an example of such a solvent, an alcohol, such as methanol or ethanol, and acetone Preferably, the amount of organic solvent should not exceed 50% by weight of the water used for
la réaction.the reaction.
Le temps de réaction dépendra de la température de réaction et de la composition désirée du complexe d'inclusion En The reaction time will depend on the reaction temperature and the desired composition of the inclusion complex En
général, il sera de 3 à 25 heures, par exemple de 16 à 22 heures. generally it will be from 3 to 25 hours, for example from 16 to 22 hours.
Comme exemple de gaz inerte approprié pour la réaction de As an example of an inert gas suitable for the reaction of
l'invention on peut citer l'azote.the invention may be mentioned nitrogen.
Selon un aspect préféré du procédé de l'invention, on chauffe une solution de cyclodextrine dans de l'eau, sous atmosphère d'azote et à une température élevée, par exemple 800 C, et on ajoute ensuite le RCI et éventuellement un solvant organique tel que l'éthanol Après refroidissement, on élimine l'eau du mélange afin d'obtenir le complexe d'inclusion de cyclodextrine et du RCI La quantité de RCI présente dans le complexe d'inclusion peut varier, généralement d'environ 0,01 % à un maximum d'environ 12,0 % en poids, en fonction de la température, du temps de réaction et de la quantité relative de RCI et de cyclodextrine mis en jeu dans la réaction En général, la quantité de RCI présente dans le complexe d'inclusion varie entre 5 et 12 %, de préférence entre 8 et 12 % en poids Des exemples de complexes d'inclusion appropriés selon According to a preferred aspect of the process of the invention, a solution of cyclodextrin is heated in water, under a nitrogen atmosphere and at an elevated temperature, for example 800 ° C., and then the RCI and optionally an organic solvent are added. such as ethanol After cooling, the water is removed from the mixture in order to obtain the inclusion complex of cyclodextrin and of the RCI The amount of RCI present in the inclusion complex can vary, generally around 0.01 % to a maximum of about 12.0% by weight, depending on the temperature, the reaction time and the relative amount of RCI and cyclodextrin involved in the reaction In general, the amount of RCI present in the inclusion complex varies between 5 and 12%, preferably between 8 and 12% by weight Examples of suitable inclusion complexes according to
l'invention contiennent par exemple de 8 à 10 % en poids de RCI. the invention contain for example 8 to 10% by weight of RCI.
Comme exemples de formes de cyclodextrines particuliè- As examples of particular cyclodextrin forms
rement appropriées pour une utilisation selonl'invention on peut citer les mélanges de cyclodextrines et plus préférablement la B-cyclodextrine. Le complexe d'inclusion est une poudre microcristalline fine On peut l'utiliser comme insecticide en l'appliquant à l'insecte ou à son milieu en une quantité efficace comme insecticide, Le traitement des insectes peut être effectué par ingestion ou par exposition des insectes aux vapeurs du RCI qui sont libérées lentement par le complexe La quantité efficace comme insecticide peut varier dans de larges limites en fonction de divers facteurs tels que le mode d'application, le RCI et l'insecte concerné En général, elle se situe entre 0,001 pg h 25,0 pg de RCI par insecte Le complexe d'inclusion peut être utilisé tel quel ou Rely suitable for use according to the invention, mention may be made of mixtures of cyclodextrins and more preferably B-cyclodextrin. The inclusion complex is a fine microcrystalline powder. It can be used as an insecticide by applying it to the insect or its medium in an amount effective as an insecticide. The treatment of insects can be carried out by ingestion or by exposure of the insects to RCI vapors which are slowly released by the complex The effective amount as an insecticide can vary within wide limits depending on various factors such as the method of application, RCI and the insect concerned In general, it is between 0.001 pg h 25.0 pg RCI per insect The inclusion complex can be used as is or
sous forme d'une composition insecticide. in the form of an insecticide composition.
Lorsque la poudre est employée telle quelle ou sous une forme d'application solide, elle peut par exemple être répartie dans des fentes et autres espaces vides dans les habitations et établissements publics, pour la lutte contre les insectes rampants, tels que les cafards et les fourmis Elle peut être incorporée dans des aliments stockés pour lutter contre les insectes nuisibles des aliments tels que le ver de la farine On peut la mélanger au sol When the powder is used as it is or in the form of a solid application, it can for example be distributed in slots and other empty spaces in dwellings and public establishments, for the control of crawling insects, such as cockroaches and ants It can be incorporated into stored food to fight against harmful insects from food such as mealworm It can be mixed with the ground
autour des cultures et autres plantes ou on peut la répandre par- around crops and other plants where it can be spread through
poudrage sur les plantes mêmes On peut également l'appliquer autour ou à l'entrée des nids de fourmis pour combattre les fourmis dans dusting on the plants themselves It can also be applied around or at the entrance to ant nests to fight ants in
les champs, comme celles de la famille Solenopsis geminata. fields, like those of the Solenopsis geminata family.
f 43403 Les complexes d'inclusion selon l'invention peuvent également être utilisés sous forme de compositions insecticides, en association avec un diluant acceptable en agriculture De telles compositions font également partie-de la présente invention Les compositions peuvent être utilisées sous forme solide ou liquide, par exemple sous forme de poudre pour poudrage ou de poudre mouillable, et contiennnent en général de 0,01 à 90 % en poids de f 43403 The inclusion complexes according to the invention can also be used in the form of insecticide compositions, in combination with a diluent acceptable in agriculture. Such compositions also form part of the present invention. The compositions can be used in solid or liquid form. , for example in the form of dusting powder or wettable powder, and generally contain from 0.01 to 90% by weight of
complexe d'inclusion de l'invention. inclusion complex of the invention.
L'expression "diluant" telle qu'utilisée dans la présente The term "thinner" as used herein
description désigne une matière liquide ou solide acceptable en description means a liquid or solid material acceptable in
agriculture qui peut être ajoutée au complexe d'inclusion pour le transformer en une forme applicable plus facilement ou pour obtenir une activité désirable Comme exemples de tels diluants, on peut citer le talc, le kaolin, la terre de diatomées, une matière végétale telle que l'amidon de maïs, la farine d'arachide et la farine de protéine, le xylène, l'eau etc, ladite matière végétale agriculture which can be added to the inclusion complex to transform it into a form which is more easily applicable or to obtain a desirable activity. As examples of such diluents, mention may be made of talc, kaolin, diatomaceous earth, a vegetable material such as corn starch, peanut flour and protein flour, xylene, water etc, said plant material
pouvant aussi servir d'appât pour insectes. can also be used as insect bait.
Les compositions insecticides de l'invention peuvent également comprendre d'autres adjuvants, par exemple des agents tensioactifs, des substances attractives pour insectes telles que l'acétoïne, les pyrolysats de sucre et le (Z)-9-hexadécénal, et/ou un appât pour insectes et autres pesticides tels que les carbamates, les phosphates et les pyréthroïdes de synthèse tels que le propoxur, le carbaryl, le naled, le dichlorvos, la resméthrine, la perméthrine The insecticidal compositions of the invention can also comprise other adjuvants, for example surfactants, insect-attracting substances such as acetoin, sugar pyrolysates and (Z) -9-hexadecenal, and / or a bait for insects and other pesticides such as carbamates, phosphates and synthetic pyrethroids such as propoxur, carbaryl, naled, dichlorvos, resmethrin, permethrin
et le fluvalinate.and fluvalinate.
Les formes concentrées des compositions de l'invention contiennent généralement de 2 à 90 % du complexe d'inclusion de l'invention Les formes d'application des compositions de l'invention contiennent généralement de 0,01 à 20 % en poids du The concentrated forms of the compositions of the invention generally contain from 2 to 90% of the inclusion complex of the invention The forms of application of the compositions of the invention generally contain from 0.01 to 20% by weight of the
complexe d'inclusion de l'invention. inclusion complex of the invention.
Les complexes d'inclusion peuvent être utilisés pour combattre les insectes indiqués dans les brevets américains no 3 904 662 et 4 021 461; les complexes d'inclusion de l'invention contenant de l'hydroprène sont particulièrement utiles contre les cafards et les fourmis, ceux contenant du méthoprène sont particulièrement utiles contre les puces telles que Tenocephalides felis, les fourmis et les cafards, et ceux contenant du kinoprène sont particulièrement utiles contre les-insectes suceurs phytophages The inclusion complexes can be used to control the insects listed in U.S. Patent Nos. 3,904,662 and 4,021,461; the inclusion complexes of the invention containing hydroprene are particularly useful against cockroaches and ants, those containing methoprene are particularly useful against fleas such as Tenocephalides felis, ants and cockroaches, and those containing kinoprene are particularly useful against phytophagous sucking insects
tels que les mouches blanches et la cochenille. such as whiteflies and cochineal.
Le complexe d'inclusion de méthoprène se prête particulièrement bien à une application par poudrage pour la lutte The methoprene inclusion complex lends itself particularly well to powder application for control
contre les puces sur les animaux tels que les chiens et les chats. against fleas on animals such as dogs and cats.
On peut l'utiliser à l'extérieur des maisons pour la lutte contre It can be used outside homes for the fight against
les puces, par exemple en le répandant par poudrage sur le gazon. fleas, for example by spreading it by dusting on the lawn.
Les exemples suivants illustrent la présente invention sans aucunement en limiter la portée Les parties s'entendent en The following examples illustrate the present invention without in any way limiting its scope The parties agree
poids et les températures sont données en degrés Celsius. weights and temperatures are given in degrees Celsius.
Exemple 1 Complexe d'inclusion de 5-cyclodextrine et d'hydroprène Sous atmosphère d'azote on chauffe à 800 une solution de ,0 g de 3cyclodextrine et 150 ml d'eau A la solution chaude de cyclodextrine on ajoute une solution de 3,0 g d'hydroprène dans ml d'éthanol absolu et on laisse refroidir lentement le mélange résultant à la température ambiante, sous agitation et sous atmosphère d'azote Après 22 heures d'agitation, on élimine l'eau à l'aide d'un évaporateur rotatif, initiallement à la pression de la trompe a eau et à une température du bain comprise entre 45 et 500, et ensuite sous un vide de 0,1 mm à la température ambiante On lave le solide 3 fois avec de l'éther, on le filtre et on le sèche sous vide, ce qui donne le complexe d'inclusion de 5-cyclodextrine et EXAMPLE 1 Inclusion Complex of 5-Cyclodextrin and Hydroprene Under a nitrogen atmosphere, a solution of. 0 g of 3cyclodextrin and 150 ml of water is heated to 800. To a hot solution of cyclodextrin, a solution of 3 is added. 0 g of hydroprene in ml of absolute ethanol and the resulting mixture is allowed to cool slowly to room temperature, with stirring and under a nitrogen atmosphere. After 22 hours of stirring, the water is removed using a rotary evaporator, initially at the pressure of the water pump and at a bath temperature between 45 and 500, and then under a vacuum of 0.1 mm at room temperature The solid is washed 3 times with ether , it is filtered and dried under vacuum, which gives the inclusion complex of 5-cyclodextrin and
d'hydroprène ( 8,0 % en poids d'hydroprène). hydroprene (8.0% by weight of hydroprene).
Exemple 2: Complexe d'inclusion de 5-cyclodextrine et de méthoprène On répète le procédé de l'exemple 1 en utilisant 3,0 9 de méthoprène à la place des 3,0 g d'hydroprène et on agite le mélange pendant 16 heures au lieu de 22 heures Le composé du titre résultant est une poudre blanche très fine contenant 9,3 % en poids Example 2: Inclusion complex of 5-cyclodextrin and methoprene The process of Example 1 is repeated using 3.09 of methoprene in place of the 3.0 g of hydroprene and the mixture is stirred for 16 hours instead of 22 hours The resulting title compound is a very fine white powder containing 9.3% by weight
de méthoprène.of methoprene.
Exemple 3: Complexe d'inclusion de 6-cyclodextrine et de kinoprène On répète le procédé de l'exemple 1 en utilisant le kinoprène à la place de l'hydroprène pour obtenir le composé du titre. Exemple 4: Poudre pour poudrage On mélange et on broye 12,5 parties du complexe Example 3: Inclusion complex of 6-cyclodextrin and kinoprene The process of Example 1 is repeated using kinoprene in place of hydroprene to obtain the title compound. EXAMPLE 4 Powder for Dusting 12.5 parts of the complex are mixed and ground
d'inclusion tel qu'obtenu à l'exemple i avec 87,5 parties de talc. of inclusion as obtained in Example i with 87.5 parts of talc.
On obtient une poudre pour poudrage contenant 1,0 % en poids d'hydroprène. Exemple 5: Poudre mouillable On mélange 82 parties du complexe d'inclusion obtenu à l'exemple 1 avec une partie de laurylsulfate de sodium, 3 parties A powder for dusting is obtained containing 1.0% by weight of hydroprene. Example 5 Wettable Powder 82 parts of the inclusion complex obtained in Example 1 are mixed with one part of sodium lauryl sulfate, 3 parts.
de ligninesulfonate, 4 parties de silice et 10 parties de kaolin. of ligninsulfonate, 4 parts of silica and 10 parts of kaolin.
On broye le mélange dans un moulin à jet d'air jusqu'à une dimension des particules sensiblement inférieure à 30 microns, et on mélange à nouveau la poudre La poudre mouillable résultante contient 6,5 % d'hydroprène et est facilement dispersable dans l'eau pour former The mixture is ground in an air jet mill to a particle size substantially less than 30 microns, and the powder is again mixed. The resulting wettable powder contains 6.5% hydroprene and is easily dispersible in water. to form
une suspension pulvérisable.a sprayable suspension.
Claims (6)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48053483A | 1983-03-30 | 1983-03-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2543403A1 true FR2543403A1 (en) | 1984-10-05 |
| FR2543403B1 FR2543403B1 (en) | 1990-01-26 |
Family
ID=23908333
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR848404887A Expired - Lifetime FR2543403B1 (en) | 1983-03-30 | 1984-03-27 | NOVEL CYCLODEXTRIN INCLUSION COMPLEXES, THEIR PREPARATION AND THEIR USE AS INSECTICIDES |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS59219202A (en) |
| AT (1) | ATA105684A (en) |
| AU (1) | AU2617684A (en) |
| BE (1) | BE899252A (en) |
| CH (1) | CH660193A5 (en) |
| DE (1) | DE3410319A1 (en) |
| DK (1) | DK171984A (en) |
| ES (1) | ES8507574A1 (en) |
| FR (1) | FR2543403B1 (en) |
| GB (1) | GB2138293B (en) |
| HU (1) | HUT37857A (en) |
| IL (1) | IL71381A (en) |
| IT (1) | IT1199099B (en) |
| NL (1) | NL8400853A (en) |
| TR (1) | TR22227A (en) |
| ZA (1) | ZA842435B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2596617A1 (en) * | 1986-04-08 | 1987-10-09 | Orstom | Composition based on fatty acid complexed with cyclodextrins, process for its preparation and plant protection application |
| FR2647305A1 (en) * | 1989-05-27 | 1990-11-30 | Sumitomo Chemical Co | APPAT EMPOESNE FOR THE FIGHT AGAINST PEST INSECTS |
| FR2647307A1 (en) * | 1989-05-27 | 1990-11-30 | Sumitomo Chemical Co | APPAT EMPOESNE FOR THE FIGHT AGAINST PEST INSECTS |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2162529B (en) * | 1984-06-08 | 1988-03-02 | Nitrokemia Ipartelepek | B-cyclodextrin complex of benzene sulphonyl urea derivatives |
| JPS61152765A (en) * | 1984-12-27 | 1986-07-11 | Nippon Ekishiyou Kk | Synthetic resin product including compound clathrated with cyclodextrin |
| HUT49447A (en) * | 1988-03-17 | 1989-10-30 | Chinoin Gyogyszer Es Vegyeszet | Process for producing stabil acaricide amitrase-composition |
| US6663876B2 (en) | 2002-04-29 | 2003-12-16 | Piedmont Pharmaceuticals, Llc | Methods and compositions for treating ectoparasite infestation |
| CN1232539C (en) * | 2002-05-10 | 2005-12-21 | 刘云清 | Match of organic medicine and beta-cyclodextrin derivative and its preparing process |
| ES2417380B1 (en) * | 2012-01-05 | 2014-06-03 | Universidad Del Pais Vasco - Euskal Herriko Unibertsitatea | New pesticide inclusion complexes, compositions containing them and their use as pesticides |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE895769C (en) * | 1951-08-26 | 1953-11-05 | Knoll Ag | Process for the preparation of inclusion compounds of physiologically active organic compounds |
| GB1038607A (en) * | 1964-05-21 | 1966-08-10 | Harvest Queen Mill & Elevator | Powdered emulsifiable concentrate having utility as a biocide and method of making same |
| FR2216914A1 (en) * | 1972-11-20 | 1974-09-06 | Teijin Ltd |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3130121A (en) * | 1961-02-10 | 1964-04-21 | Leeco Chemican Company Divisio | Insecticidal powder |
| US4021461A (en) * | 1971-11-22 | 1977-05-03 | Zoecon Corporation | Aliphatic hydrocarbon 2,4-dienoic acids, esters and derivatives thereof |
| US3904662A (en) * | 1972-02-07 | 1975-09-09 | Zoecon Corp | 2,4-dienoic acids, esters and derivatives |
| JPS5745722B2 (en) * | 1973-07-27 | 1982-09-29 | ||
| JPS5761261B2 (en) * | 1975-01-17 | 1982-12-23 | Dainippon Jochugiku Kk | |
| US4230687A (en) * | 1978-05-30 | 1980-10-28 | Griffith Laboratories U.S.A., Inc. | Encapsulation of active agents as microdispersions in homogeneous natural polymeric matrices |
-
1984
- 1984-03-16 HU HU841058A patent/HUT37857A/en unknown
- 1984-03-16 NL NL8400853A patent/NL8400853A/en not_active Application Discontinuation
- 1984-03-21 DE DE19843410319 patent/DE3410319A1/en not_active Ceased
- 1984-03-26 TR TR22227A patent/TR22227A/en unknown
- 1984-03-27 FR FR848404887A patent/FR2543403B1/en not_active Expired - Lifetime
- 1984-03-27 GB GB08407909A patent/GB2138293B/en not_active Expired
- 1984-03-27 CH CH1522/84A patent/CH660193A5/en not_active IP Right Cessation
- 1984-03-27 BE BE1/10989A patent/BE899252A/en not_active IP Right Cessation
- 1984-03-28 AU AU26176/84A patent/AU2617684A/en not_active Abandoned
- 1984-03-28 DK DK171984A patent/DK171984A/en not_active IP Right Cessation
- 1984-03-28 ES ES531056A patent/ES8507574A1/en not_active Expired
- 1984-03-28 IL IL71381A patent/IL71381A/en not_active IP Right Cessation
- 1984-03-29 IT IT47964/84A patent/IT1199099B/en active
- 1984-03-29 AT AT0105684A patent/ATA105684A/en not_active IP Right Cessation
- 1984-03-29 JP JP59063121A patent/JPS59219202A/en active Granted
- 1984-03-30 ZA ZA842435A patent/ZA842435B/en unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE895769C (en) * | 1951-08-26 | 1953-11-05 | Knoll Ag | Process for the preparation of inclusion compounds of physiologically active organic compounds |
| GB1038607A (en) * | 1964-05-21 | 1966-08-10 | Harvest Queen Mill & Elevator | Powdered emulsifiable concentrate having utility as a biocide and method of making same |
| FR2216914A1 (en) * | 1972-11-20 | 1974-09-06 | Teijin Ltd |
Non-Patent Citations (2)
| Title |
|---|
| PROCEEDINGS OF THE FIRST INTERNATIONAL SYMPOSIUM ON CYCLODEXTRINS, Budapest, 30 septembre - 2 octobre 1981, éd. J.Szejtli, pages 15-24, D.Reidel Publishing Company, Dordrecht, NL; T.NAGAI: "Cyclodextrin research in Japan" * |
| R.WEGLER: "Chemie der Pflanzenschutz- und Sch{dlingsbek{mpfungsmittel", vol. 6, 1981, pages 185-214, Springer-Verlag, Berlin, DE; J.P.EDWARDS et al.: "The use of Juvenoids in insect pest management" * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2596617A1 (en) * | 1986-04-08 | 1987-10-09 | Orstom | Composition based on fatty acid complexed with cyclodextrins, process for its preparation and plant protection application |
| FR2647305A1 (en) * | 1989-05-27 | 1990-11-30 | Sumitomo Chemical Co | APPAT EMPOESNE FOR THE FIGHT AGAINST PEST INSECTS |
| FR2647307A1 (en) * | 1989-05-27 | 1990-11-30 | Sumitomo Chemical Co | APPAT EMPOESNE FOR THE FIGHT AGAINST PEST INSECTS |
| TR25619A (en) * | 1989-05-27 | 1993-07-01 | Sumitomo Chemical Co | A TOXIC TRAP FEED FOR THE CONTROL OF HARMFUL DAMAGE. |
| US5300293A (en) * | 1989-05-27 | 1994-04-05 | Sumitomo Chemical Co., Ltd. | Poison bait for control of noxious insects |
Also Published As
| Publication number | Publication date |
|---|---|
| GB8407909D0 (en) | 1984-05-02 |
| IT8447964A1 (en) | 1985-09-29 |
| IL71381A (en) | 1987-09-16 |
| IT1199099B (en) | 1988-12-30 |
| NL8400853A (en) | 1984-10-16 |
| JPH0572361B2 (en) | 1993-10-12 |
| GB2138293A (en) | 1984-10-24 |
| HUT37857A (en) | 1986-03-28 |
| CH660193A5 (en) | 1987-03-31 |
| IT8447964A0 (en) | 1984-03-29 |
| BE899252A (en) | 1984-09-27 |
| TR22227A (en) | 1986-10-09 |
| ES531056A0 (en) | 1985-09-16 |
| GB2138293B (en) | 1986-07-02 |
| ES8507574A1 (en) | 1985-09-16 |
| AU2617684A (en) | 1984-10-04 |
| ZA842435B (en) | 1985-11-27 |
| ATA105684A (en) | 1988-10-15 |
| JPS59219202A (en) | 1984-12-10 |
| FR2543403B1 (en) | 1990-01-26 |
| DE3410319A1 (en) | 1984-12-13 |
| DK171984D0 (en) | 1984-03-28 |
| DK171984A (en) | 1984-10-01 |
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