GB2138293A - Novel pesticidal compositions and their use - Google Patents

Novel pesticidal compositions and their use Download PDF

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Publication number
GB2138293A
GB2138293A GB08407909A GB8407909A GB2138293A GB 2138293 A GB2138293 A GB 2138293A GB 08407909 A GB08407909 A GB 08407909A GB 8407909 A GB8407909 A GB 8407909A GB 2138293 A GB2138293 A GB 2138293A
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United Kingdom
Prior art keywords
inclusion complex
cyclodextrin
insect growth
growth regulator
hydroprene
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.)
Granted
Application number
GB08407909A
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GB8407909D0 (en
GB2138293B (en
Inventor
Robert L Carney
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Sandoz AG
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Sandoz AG
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Filing date
Publication date
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Publication of GB8407909D0 publication Critical patent/GB8407909D0/en
Publication of GB2138293A publication Critical patent/GB2138293A/en
Application granted granted Critical
Publication of GB2138293B publication Critical patent/GB2138293B/en
Expired legal-status Critical Current

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Classifications

    • 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
    • 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
    • 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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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Zoology (AREA)
  • Agronomy & Crop Science (AREA)
  • Environmental Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Biochemistry (AREA)
  • Toxicology (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Molecular Biology (AREA)
  • Materials Engineering (AREA)
  • Insects & Arthropods (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A novel cyclodextrin inclusion complex which comprises cyclodextrin and an insect growth regulator selected from hydroprene, methoprene and kinoprene, and the use thereof for the control of insects.

Description

SPECIFICATION Novel pesticidal compositions and their use This invention relates to a novel cyclodextrin inclusion complex which comprises cyclodextrin and an insect growth regulator selected from hydroprene, methoprene and kinoprene, and the use of the complex for the control of insects.
The compound "hydroprene" is ethyl (2E,4E) 3,7,11 -trimethyl-2,4-dodecadienoate, described in U.S. Patent 4,021,461. The compound "methoprene" is isopropyl (2E,4E)-11 -methoxy-3,7,1 1 -trimethyl-2,4- dodecadienoate, described in U.S. Patent 3,904,662.
The compound "kinoprene" is prop-2-ynyl (2E,4E) 3,7,11 -trimethyl-2,4-dodecadienoate, described in said patent 4,021,461.
These compounds are insect control agents of the type known as juvenile hormone analogs or insect growth regulators (lobs), which interfere with the metamorphosis of immature insects, causing abnormal development which leads to death or to the inability to reproduce.
While hydropene, methoprene and kinoprene are active IGRs, it has been discovered that their activity is greatly increased and enhanced when they are interacted with cyclodextrin to make an inclusion complex. The complex is unexpectedly superior to the IGR alone, showing greatly improved stability and efficacy. When the complex is included in a bait formulation, the bait is much less repellantto the target insects and is thus more effective. The inclusion complex appears to provide chemical and photo-stability to, and resistance to evaporation of, the IGR.
Crude cyclodextrin can be prepared from potato starch by fermentation with an alkaline amylase obtained from a strain of Bacillus macerans following the procedure of Japan Kokai 74/117,691. Alternatively, a resin-bound enzyme can be used to prepare a mixture of cylodextrins (Chem. Abs.
86:87657). Pure p-cyclodextrin can be prepared from sweet potato starch dextrin, as disclosed in German OLS 25 32 051 or by K. Horikoshi, Process Biochemistry 14, pages 26-28,30(1979).
The inclusion complex of the preent invention can be prepared by reacting an insect growth regulator selected from hydropene, methoprene and kinoprene with cyclodextrin in water under inert gas atmosphere.
The reaction is preferably effected in the presence of minor parts of water soluble organic solvents capable of increasing the solubility of the GRin water. Examples of such solvents are e.g. alcohols such as methanol or ethanol and acetone. The amount of organic solvent should preferably not exceed 50 % by weight of the water employed in the reaction.
The reaction time will be dependent on the reaction temperature and on the desired composition of the inclusion complex. In general it will be between 3 and 25 hours, e.g. between 16 to 22 hours.
An example of an inert gas, suitable for use in the reaction of the invention is N2.
According to a preferred aspect of the process of the invention, a solution of cyclodextrin in water is heated under nitrogen to an elevated temperature, e.g. 80"C, after which the IGR, and optionally an organic solvent such as ethanol, is added. After cooling, the water is removed from the mixture to yield the cyclodextrin inclusion complex of the IGR.
The amount of the IGR present in the inclusion complex can vary, generally from about 0.01 weight percent to a maximum of about 12.0 weight percent, depending apparently on the temperature, the reaction time and the relative amount of IGR and cyclodextrin introduced in the reaction. In general the amount of IGR present in the inclusion complex will vary between 5 and 12, preferably between 8 and 12 percent by weight. Suitable examples of inclusion complexes of the invention contain e.g. 8 to 10 percent by weight of IGR.
Examples of cyclodextrin forms particularly appropriate for use in the invention are mixtures of cyclodextrins and, more preferably, p-cyclodextrin.
The inclusion complex is a fine microcrystalline powder or dust. It can be used as insecticide by applying it to the insect or its locus in an insecticidally effective amount. The treatment of insects can be achieved by ingestion or by exposure of the insects to vapors of the IGR which are slowly released by the complex. The insecticidally effective amount may vary between very wide ranges, depending on various factors such as the mode of application, the IGR and the insect involved; in general, it is of the order of 0.001 9 to 25.0 9 of IGR per insect. The inclusion complexes may be employed as such or in the form of an insecticidal composition.
When employed as such or in solid application form, the powder can, for example, be distributed in crevices and other deadspace areas in homes and institutions for the control of crawling insects, such as cockroaches and ants. It can be incorporated in stored food materials to control stored food pests, such as the flour beetle. It can be mixed into the soil around crops or other plants or can be dusted onto the plants themselves. It can also be applied around or in the entrances to ant nest sites for the control of ants in the field, such as fire ants.
The inclusion complex of the invention may also be employed as an insecticidal composition in association with an agriculturally acceptable diluent.
Such insecticidal compositions also form part of the present invention. They may be employed in either solid or liquid forms, e.g. in the form of a dustable powder or a wettable powder and include, in general, from 0.01 to 90% by weight of the inclusion complex of the invention.
The term diluent as used herein means any liquid or solid agriculturally acceptable material which may be added to the inclusion complex to bring it in an improved applicable form, respectively to a desirable desirable strength of activity. It can for example be talc, kaolin, diatomaceous earth, a vegetable material (such as corn starch, peanut meal or protein meal), xylene, water and the like, said vegetable material can also serve as insect bait.
The insecticidal compositions of the invention may also comprise other formulation ingredients, e.g. surfactants, insect attractants such as acetoin, sugar pyrolysate and (Z)-9-hexadecenal, and/or an insect bait or other pesticides such as the carbamates, phosphates and synthetic pyrethroids, e.g.
propoxur, carbaryl, naled, dichlorvos, resmethrin, permethrin, and fluvalinate.
Concentrate forms of the compositions of the invention generally contain from 2 to 90% of the inclusion complex of the invention. Application forms of the composition of the invention generally contain from 0.01% to 20% by weight of the inclusion complex of the invention.
The inclusion complex can be used for the control of the insects indicated in U.S. Patents 3,904,662 and 4,021,461: inclusion complexes of the invention containing said hydropene are particularly useful agianst 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 plant sucking insects such as white flies and scale.
The methoprene inclusion complex lends itself particulary good to dust application for the control of fleas on animals such as dogs and cats. It can be used also around the home for outdoor flea control such as by dust application to the turf.
The following examples are provided to illustrate the practice of the present invention. Temperature is given in degrees Centigrade. The term "wt. %" indicates percentage by weight of the total composition.
EXAMPLE 1 ss-Cyclodextrin inclusion complex of hydroprene Asolution of 15.0g of p-cyclodextrin and 150 ml of water is heated under nitrogen to 80 . A solution of hydroprene dissolved in 15 ml of anhydrous ethanol is added to the hot solution of cyclodextrin. The resulting mixture is allowed to cool slowly to room temperature with stirring under nitrogen. After 22 hours of stirring, the water is removed by rotoevaporation, initially at aspirator pressure and a bath temperature of 45-50", then at 0.1 mm vacuum, room temperature. The solid is washed (3 x) with ether, filtered and dried under vacuum to give the ss- cyclodextrin dextrin inclusion complex of hydropene (8.0 wt. % of hydropene).
EXAMPLE 2 -Cyclodextrin inclusion complex of methoprene The process of Example 1 is repeated except that 3.0 g methoprene in place of 3.0 g hydroprene is used and that the mixture is stirred for 16 hours in place of 22 hours. The resulting title compound is a very fine white powder containing 9.3 wt. % of methoprene.
EXAMPLE 3 ss-Cyclodextrin inclusion complex of kinoprene The process of Example 1 is repeated using the IGR kinoprene in place of hydroprene to produce the title compound.
EXAMPLE 4 Dustable powder 12.5 Parts of the inclusion complex as obtained according to Example 1 are mixed and milled with 87.5 pats of talc. A dustable powder containing 1.0 wt. % of hydroprene is obtained.
EXAMPLE 5 Wettable Powder 82 Parts of the inclusion complex as obtained according to Example 1 (assay: 8.0 % hydroprene) are mixed with 1 part sodium lauryl sulphate, 3 parts lignin sulphate, 4 parts of silica and 10 parts of kaolin. This mixture is milled in an air jet mill until the particles are substantially below 30 microns, then the powder is mixed again. The resulting wettable powder contains 6.5 % of hydroprene and is easily dispersible in water to form a sprayable suspension.

Claims (19)

1. Process for preparing a cyclodextrin inclusion complex comprising cyclodextrin and an insect growth regulator from hydroprene, methoprene and kinoprene, characterised in that the insect growth regulator is reacted with cyclodextrin in water under inert gas atmosphere.
2. A process according to Claim 1, substantially as described herein by way of example.
3. A complex obtained by a process according to Claim 1 or2.
4. A cyclodextrin inclusion complex which comprises cyclodextrin and an insect growth regulator selected from hydroprene, methoprene and kinoprene.
5. An inclusion complex according to Claim 4 wherein the insect growth regulator is present in from 0.01 to 12.0 weight percent of the inclusion complex.
6. An inclusion complex according to Claim 5 wherein the amount of insect growth regulator is from 5.0 to 12.0 weight percent of the inclusion complex.
7. An inclusion complex according to Claim 6 wherein the amount of insect growth regulator is from 8.0 to 12.0 weight percent of the inclusion complex.
8. An inclusion complex according to Claim 7 wherein the cyclodextrin is ss-cylcodextrin.
9. An inclusion complex according to Claim 8 wherein the insect growth regulator is hydroprene.
10. An inclusion complex according to Clain 8 wherein the insect growth regulator is methopene.
11. An inclusion complex according to Claim 8 wherein the insect growth regulator is kinoprene.
12. A method for the control of insects which comprises treating the insect or its locus with an insect growth regulating effective amount of an inclusion complex as defined in Claim 4.
13. The method according to Claim 12 wherein the cyclodextrin is p-cyclodextrin.
14. The method according to Claim 13 wherein the amount of insect growth regulator is from 0.01 to 12.0 weight percent of the inclusion complex.
15. The method according to Claim 14 wherein the amount of insect growth regulator is from 8.0 to 12.0 weight percent of the inclusion complex.
16. The method according to Claim 14 wherein the insect is a cockroach and the insect growth regulator is hydroprene.
17. An insecticidal composition comprising a cyclodextrin inclusion complex of cyclodextrin and an insect growth reglator selected from hydroprene, methoprene and kinoprene in association with an agriculturally acceptable diluent.
18. A composition according to Claim 17 in concentrate form comprising from 2 to 90% by weight of the inclusion complex.
19. A composition according to Claim 17 in application form comprising from 0.01 to 20% by weight of the inclusion complex.
GB08407909A 1983-03-30 1984-03-27 Novel pesticidal compositions and their use Expired GB2138293B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US48053483A 1983-03-30 1983-03-30

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GB8407909D0 GB8407909D0 (en) 1984-05-02
GB2138293A true GB2138293A (en) 1984-10-24
GB2138293B GB2138293B (en) 1986-07-02

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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 (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2162529A (en) * 1984-06-08 1986-02-05 Nitrokemia Ipartelepek beta -Cyclodextrin complex of benzene sulphonyl urea derivatives
GB2218337A (en) * 1988-03-17 1989-11-15 Cyclolab Cyclodextrin Kutato F Stable acaricidal composition
US5300293A (en) * 1989-05-27 1994-04-05 Sumitomo Chemical Co., Ltd. Poison bait for control of noxious insects
WO2003095498A1 (en) * 2002-05-10 2003-11-20 Yunqing Liu Complex of organic medicines and beta-cyclodextrin derivatives and its preparing process
US6663876B2 (en) 2002-04-29 2003-12-16 Piedmont Pharmaceuticals, Llc Methods and compositions for treating ectoparasite infestation
EP2848122A4 (en) * 2012-01-05 2015-09-09 Univ Del País Vasco Euskal Herriko Unibertsitatea Upv Ehu New pesticide inclusion complexes, compositions containing said complexes and the use thereof as pesticides

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61152765A (en) * 1984-12-27 1986-07-11 Nippon Ekishiyou Kk Synthetic resin product including compound clathrated with cyclodextrin
FR2596617B1 (en) * 1986-04-08 1990-10-05 Orstom COMPOSITION BASED ON FATTY ACID COMPLEXED BY CYCLODEXTRINS, ITS PREPARATION METHOD AND PHYTOSANITARY APPLICATION
JP2974373B2 (en) * 1989-05-27 1999-11-10 住友化学工業株式会社 Poison bait for pest control

Family Cites Families (9)

* Cited by examiner, † Cited by third party
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
US3130121A (en) * 1961-02-10 1964-04-21 Leeco Chemican Company Divisio Insecticidal powder
DE1542902A1 (en) * 1964-05-21 1970-04-16 Harvest Queen Mill & Elevator Emulsifiable powder concentrate suitable as a biocide
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
JPS5017529B2 (en) * 1972-11-20 1975-06-21
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

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2162529A (en) * 1984-06-08 1986-02-05 Nitrokemia Ipartelepek beta -Cyclodextrin complex of benzene sulphonyl urea derivatives
GB2218337A (en) * 1988-03-17 1989-11-15 Cyclolab Cyclodextrin Kutato F Stable acaricidal composition
US5300293A (en) * 1989-05-27 1994-04-05 Sumitomo Chemical Co., Ltd. Poison bait for control of noxious insects
US6663876B2 (en) 2002-04-29 2003-12-16 Piedmont Pharmaceuticals, Llc Methods and compositions for treating ectoparasite infestation
US8178116B2 (en) 2002-04-29 2012-05-15 Piedmont Pharmaceuticals, Llc Methods and compositions for treating ectoparasite infestation
US8815270B2 (en) 2002-04-29 2014-08-26 Piedmont Pharmaceuticals, Llc Methods and compositions for treating ectoparasite infestation
WO2003095498A1 (en) * 2002-05-10 2003-11-20 Yunqing Liu Complex of organic medicines and beta-cyclodextrin derivatives and its preparing process
EP2848122A4 (en) * 2012-01-05 2015-09-09 Univ Del País Vasco Euskal Herriko Unibertsitatea Upv Ehu New pesticide inclusion complexes, compositions containing said complexes and the use thereof as pesticides

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Publication number Publication date
HUT37857A (en) 1986-03-28
FR2543403B1 (en) 1990-01-26
ZA842435B (en) 1985-11-27
ES531056A0 (en) 1985-09-16
GB8407909D0 (en) 1984-05-02
TR22227A (en) 1986-10-09
GB2138293B (en) 1986-07-02
CH660193A5 (en) 1987-03-31
FR2543403A1 (en) 1984-10-05
ATA105684A (en) 1988-10-15
JPH0572361B2 (en) 1993-10-12
AU2617684A (en) 1984-10-04
IL71381A (en) 1987-09-16
DK171984D0 (en) 1984-03-28
IT1199099B (en) 1988-12-30
IT8447964A0 (en) 1984-03-29
BE899252A (en) 1984-09-27
JPS59219202A (en) 1984-12-10
NL8400853A (en) 1984-10-16
ES8507574A1 (en) 1985-09-16
DE3410319A1 (en) 1984-12-13
DK171984A (en) 1984-10-01
IT8447964A1 (en) 1985-09-29

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Effective date: 19950327