CA1312821C - Compositions and methods for controlling cockroaches - Google Patents

Compositions and methods for controlling cockroaches

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Publication number
CA1312821C
CA1312821C CA000508868A CA508868A CA1312821C CA 1312821 C CA1312821 C CA 1312821C CA 000508868 A CA000508868 A CA 000508868A CA 508868 A CA508868 A CA 508868A CA 1312821 C CA1312821 C CA 1312821C
Authority
CA
Canada
Prior art keywords
hydroprene
composition according
cockroach
compositions
diluent
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.)
Expired - Lifetime
Application number
CA000508868A
Other languages
French (fr)
Inventor
Gustave K. Kohn
David L. Grant
Robin R. Rudolph
Gerardus B. Staal
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.)
Novartis AG
Original Assignee
Sandoz AG
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 Sandoz AG filed Critical Sandoz AG
Application granted granted Critical
Publication of CA1312821C publication Critical patent/CA1312821C/en
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Expired - Lifetime legal-status Critical Current

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Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N49/00Biocides, 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)
  • Agronomy & Crop Science (AREA)
  • Insects & Arthropods (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Catching Or Destruction (AREA)

Abstract

Case 133-0630 NOVEL COMPOSITIONS AND METHODS FOR CONTROLLING COCKROACHES

Abstract of the Disclosure The invention relates to novel compositions and methods for cockroach populations using the (S)-(+) hydroprene.

Description

1 31 28~1 Case 133-0630 NOVEL COMPOSITIONS AND MTHODS FOR CONTROLLIN~ COCKROACHES
This invention relates to novel compositions and methods for contro1-ling cockroach populations using the (S)-(+) enantiomer of hydroprene.
Hydroprene is ethyl (2E,4E)-3,7,11-trimethyl-2,4-dodecadienoate. it is known to have juvenile hormone activity on insects e.g. cockroaches such as Blattella germanica (see i.a. J. Econ Entom (1975) 68:46-48).
There is an asymmetric carbon atom at C-7 in hydroprene and, accord-ingly, there are R and S enantiomers of the compound. J Agric Food Chem (1978) 26:542-550 reports comparative juvenile hormone activity tests on (S)-(+) hydroprene, (R)-(-) hydroprene and the racemic mixture on Aedes aegypti, Galleria mellonella, Tenebrio molitor, Musca domestica, and Heliothis virescens. These tests showed that the (S)-(+) enantiomer showed approximately twice the activity of the racemic mixture on these insect species.
It has now surprisingly been found that (S)-(+) hydroprene exhibits-`~ unexpectedly superior juvenile hormone activity on cockroaches relative to racemic hydroprene.~
Accordingly, one aspect of the invention is a method of cockroach population control comprising administering a cockroach reproduction 20 inhibiting amount of (S)-(+) hydroprene to the locus infested by said population.
The term ~S)-(+) hydroprene as used herein is intended to relate to hydroprene comprising substantially more than 50% by weight of the (S)-(+)-enantiomer. Preferably the hydroprene used in the invention is composed 25 predominantly of (S)-(+) hydroprene, i.e. comprises more than 75% by weight of (S)-(+) hydroprene. More preferably, the hydroprene contains less than 10%, particularly less than 5% by weight of the (R) enantiomer and is most preferably substantially free of the (R) enantiomer (i.e. contains less than 2% by weight of the (R) enantiomer).
Another aspect of the invention is a pest controlling composition comprising:
a) (S)-(+) hydroprene b) a diluent ~;

~ ~.
and c) where the diluent is a solvent, at least one adiuvant selected frcm a propellant, a surfactant and a thickener (hereinafter composition of the invention).
The term diluent as used herein means any liquid or solid agricul-5 turally acceptable material which may be added to the active ingredient tobring it in an easier or improved applicable form. It includes carriers and solvents and can for example by calcium carbonate, talc, kaolin, clay, diatomaceous earth, resins (such as polyvinyl chloride, polyester urethane ethylene vinyl acetate, polypropylene), polyethylene, xylene, a petroleum 10 solvent (including ligroin, benzin, naphta, a hydrocarbone such as pentane, hexane, octane), an alkanol such as isopropanol, a chlorinated hydrocarbon (e.g. CH2C12, CC13CH3), glycol monoalkylether, water and the like.
The term propellant relates to an agriculturally acceptable liquified gas which is self pressurised in a container having a valve and 15 comprising a pest controlling composition, which gas forces the contents from the container ~hen the valve is activated.
The term surfactant relates to an agriculturally acceptable material ~hich imparts emulsifiability, spreading, wetting, dispersibility or other surface-modifying properties of the pest controlling composition of the 20 invention.
The term thickener relates to a material which increases the viscosity of a liquid.
(S)-(+) hydroprene may be obtained in a manner known per se by resolving hydroprene into the (S) and (R) enantiomers or by synthesizing 25 it from a resolved starting material.
(S)-(~) hydroprene exhibits a unique combination of properties vis-a-vis other juvenoids that makes it remarkably effective as a cockroach popula-tion control agent.
It is persistent in the environments that cockroaches inhabit. It is 30 sufficiently volatile to translocate from one surface to another and thus penetrate into cockroach harborages, redistribute therein, and remain accessible to resident cockroach populations. Further, (S)-(+) hydroprene is effective in inducing sterility in cockroaches as well as having other juvenoid activities. This property is essential to effective cockroach .

- -` 1312821 eradication. Finally, (S)-(+) hydroprene has a high level of acti~/ity. Its superior activity relative to racemic hydroprene means that it is muc~ more economical to use and provides less contamination of food and the human habitat than the racemic mixture.
In this regard, substantially pure (S)-(+) hydroprene has been found to provide German cockroach reproduction control in the laboratory at distribution levels as low as a few tenths of a microgram per square meter.
Higher distribution levels may be required to control populations of other cockroach species such as the American cockroach (Periplaneta americana) 10 and the oriental cockroach (81atta orientalis). Also, in actual use in the field higher distribution levels than were used in the laboratory are used. Thus, depending on the nature of the surfaces in the habitat, the roach species, the mode of application etc., the distribution level of (S~-(+) hydroprene in actual use will conveniently be in the range of 0.3 mg/m2 to 15 40mg/m2, more preferably of 3 mg/m2 to 30 mg/m2.
(S)-(+) hydroprene is typically applied in composition form suitable for use in cockroach control. Examples of compositions suitable for such use comprise aerosols (in aerosol dispensers or foggers), roach baits, roach dusts, emulsifiable concentrates, ready to use sprays, ultra low 20 volume sprays, aroma disks, roach strips and the like; such compositions may be obtained in conventional manner. The composition of the invention is conveniently applied to cockroach habitats, which habitats include human lodgings, sites where food is stored or prepared and industrial facilities.
For use of (S)-(+) hydroprene in aerosol form, the active ingredient is 25 conveniently formulated with an innocuous, volatile solvent and a propellant.
Examples of suitable volatile solvents are chlorinated alkanes such as methylene chloride or l,1,1-trichloroethane.
~ xamples of suitable propellants are low boiling alkanes such as 30 propane or butane or fluorinated hydrocarbons.
For use of (S)-(+) hydroprene in spray form, e.g. as emulsifiable concentrate or ready to use spray, the active ingredient will conveniently - be formulated with an emulsifying agent and a solvent.

~, ,, Examples of suitable emulsifiers are sorbitol, fatty acid esters, polyethoxylated fatty acid esters of alcohols or phenols, calcium dodecyl benzoate and the like.
Examples of suitable solvents are aromatic hydrocarbons such as xylene.
Solid compositions such as dusts or powders comprise (S)-(+) hydro-prene and a solid carrier.
Examples of suitable solid carriers are calcium carbonate, diato-maceous earth, clay and the like.
(S)-(+) hydroprene may also be applied in solid composition form by evaporation from a solid carrier, e.g. in the form of aroma disks and strips, particularly the latter.
Solid compositions such as aroma disks and strips will comprise (S)-(+) hydroprene, a polymer and, preferably a plasticizer.
Examples of suitable polymers (resins) are polyvinylchloride, poly-ethylene, polyurethane, polypropylene, acrylics, nylon, in particular poly-vinylchloride.
For use of (S)-(+) hydroprene in bait form, the active ingredient will conveniently be formulated with a foodstuff.
Suitable foodstuffs for use in such baits are corn meal, dog food, corn syrup and the like.
(S)-(+) hydroprene may also be used in microencapsulated form. Such microcapsules are conveniently of the gelatin of nylon type; compositions comprising microcapsules contain conveniently a thickener such as xanthan 25 gum.
The (S)-(+) hydroprene formulations of the lnvention may contain conventional additives such as U.V. stabilizers, heat stabilizers, anti-oxidants, pigments etc. They may also contain conventional insecticides such as organophosphates and pyrethroids to provide an initial knockdown 30 of a portion of the cockroach populatlon or other insects at the ap~lica-, .~ .

1 31 2~21 -5- 133-~30 tion site. They are prepared in a manner known per se. Suitable composi-tions of the invention comprise conveniently from 0.01 to 80% by weight of (S)-(+) hydroprene.
Conveniently aerosols will comprise from 0.01 to 10% by weight, emulsi-fiable concentrates and ultra low volume spray from 0.3 to 80% by weight,ready to use sprays from 0.5 to 10~ by weight and roach baits or strips from 1 to 15% by weight of (S)-(+) hydroprene.
The invention is further illustrated by the following examples. These examples are not intended to limit the invention in any manner. Parts are 10 by weight.

,~.
-6- 13~-0&30 FORMULA ION EXAMPLE
1. Aerosol A B C
(S)-(+) hydrnprene (100%) 0.021 0.064 0.1 CH2C12 17.646 16.936 16.9 3 3 54.333 55 55 propane/isobutane to 70 psi 28 28 28 2. Emulsifiable concentrate (S)-(~) hydroprene (100%) 10 antioxidant 0.2 (butylated hydroxytoluene) emulsifier 30.8 (polyoxyethylene sorbitol ester) solvent 59,0 (aliphatic hydrocarbon) 3. Ready to use spray (S)-(+) hydroprene (100%) 0.4 water 91.86 antioxidant 0,44 (butylated hydroxytoluene) emulsifier 2.0 (polyoxyethylene sorbitol ester) chelating agent ~NaEDTA) 5,0 buffering agent (citric acid) 0.3 4. Bait (S)-(+) hydroprene (100%) 1.0 2C12 5.0 corn meal 94.0 . . 5. Dust (S)-(+) hydroprene (100%) 10.0 Ethylene glycol 4.5 antioxydant (butylated hydroxy 0-5 toluene) silica 85 .. , Test 1 Foggers comprising 15 mg and 45 mg of (S)-(~) hydroprene resp., ~ormu-lated according to Formulation ~xamples lA and lB resp. are discharged in a 85 m3 fogger chamber. At the time of discharge the chamber contained cigarette papers and three different test substrates (treated vinyl tile, glass, and unpainted plywood) placed at distances of 1.8, 2.7 and 3.7 m from the fogger. This mist is allowed to settle for 20 minutes and the papers and substrates are removed. The papers are extracted and the extracts analysed to determine the amount of (S)-(~) hydroprene (in~ug/cm substrate) 10 deposited at the three distances. The depositions are in the range of 0.005 to 0.053 ~g/cm2.
After removal from the chamber the treated test substrates are placed in a laboratory under ambient conditions. Within one hour of removal, ten to twelve fifth to sixth instar German roaches are confined to each of the 15 treated substrate surfaces. Food, water and harborage is supplied.
The containers are examined daily for the first ten days. At the examination times food and water are replenished as needed. All roaches molting to the adult stage are removed and destroyed during the first ten days of the test. (Roaches in the last ten days of the last instar before 20 molt are not sensitive to juvenoids.) After day ten the containers are examined every seven to fourteen days and the following status information recorded.
Total number of surviving roaches.
Adult or nymph status of each roach.
Sex of all adult roaches.
JH effect on adult roaches if any.
Ootheca carried.
Viability of ootheca dropped.
Fl progeny produced.
The final reading is taken at week 12 after the ten-day post-treatment period.

~,.
Based on these readings the treatments are scored for overall juvenile hormone (JH) effects.
The overall JH response of (S) hydroprene was significantly better than the racemic mixture which was used as Standard. More importantly, the results of the readings on total Fl nymphs produced and Fl nymphs produced per female roach having the opportunity to mate and produce young indicate the reproduction control activity of (S)-(+) hydroprene was about 7-fold higher than the racemic mixture.
Test 2 Serial dilutions of (S)-(+) hydroprene or racemic hydroprene in acetone are applied to glass and plywood plates by dribbling the solution onto the plates from a syringe. The plates are used as floors for test cages. Each cage is supplied with harborage, water and food and 50 4th instar German cockroaches. The cages are maintained at 27C, 16 hours light cycle, 50%
15 relative humidity for about two months. Control efficacy is scored based on morphological effects and 100% inhibition of reproduction. In these tests (S)-(+) hydroprene provided 100% control of reproduction at a distri-bution of 0.1 ,ug/cm2, whereas the lowest distribution giving 100% control with racemic hydroprene was 10/ug/cm2 on glass and 1 ~ug/cm2 on plywood.

,

Claims (11)

1. A cockroach controlling composition comprising a) (S)-(+) hydroprene b) a diluent and c), where the diluent is a solvent, at least one adjuvant selected from a propellant, a surfactant and a thickener.
2. A composition according to Claim 1, comprising from 0.01 to 80%
by weight of(S)-(+) hydroprene.
3. A composition according to Claims 1 or 2 in aerosol form.
4. A composition according to Claim 1 or 2 in spray form.
5. A composition according to Claim 1 in solid form.
6. A composition according to Claim 5 in bait form.
7. A composition according to Claim 5, wherein the diluent is a polymer and comprising additionally a plasticizer.
8. A method of controlling cockroaches comprising administering a cock-roach reproduction inhibiting amount or (S)-(+) hydroprene to the locus infested by said population.
9. The method of Claim 8, wherein the distribution of (S)-(+) hydro-prene to said locus is in the range of 0.3 to 40 mg/m2.
10. The method of Claim 8 or 9, wherein the (S)-(+) hydroprene is administered in aerosol or spray form.
11. The method of Claim 8 or 9, wherein the (S)-(+) hydroprene is administered by evaporation from a solid carrier.
CA000508868A 1985-05-13 1986-05-12 Compositions and methods for controlling cockroaches Expired - Lifetime CA1312821C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US73344485A 1985-05-13 1985-05-13
US733,444 1985-05-13
BR8602190A BR8602190A (en) 1985-05-13 1986-05-14 COMPOSITION FOR PEST CONTROL AND PROCESS FOR CHEAP CONTROL

Publications (1)

Publication Number Publication Date
CA1312821C true CA1312821C (en) 1993-01-19

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ID=25664118

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CA000508868A Expired - Lifetime CA1312821C (en) 1985-05-13 1986-05-12 Compositions and methods for controlling cockroaches

Country Status (14)

Country Link
JP (1) JPH0667801B2 (en)
AT (1) AT391242B (en)
AU (1) AU589181B2 (en)
BE (1) BE904740A (en)
BR (1) BR8602190A (en)
CA (1) CA1312821C (en)
CH (1) CH667570A5 (en)
DE (1) DE3615035C2 (en)
EG (1) EG19057A (en)
FR (1) FR2581508B1 (en)
GB (1) GB2174908B (en)
IE (1) IE59071B1 (en)
NL (1) NL8601134A (en)
SU (1) SU1743330A3 (en)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2585319B2 (en) * 1987-11-30 1997-02-26 住友化学工業株式会社 Poison bait for pest control
JP2588923B2 (en) * 1988-03-01 1997-03-12 住友化学工業株式会社 Poison bait for pest control
BR8807553A (en) * 1988-04-08 1990-08-07 Sandoz Ag NEW COMPOSITION AND PROCESS TO CONTROL CHEAP POPULATION
JP2771193B2 (en) * 1988-10-20 1998-07-02 アース製薬株式会社 Pest poison composition
JP2974373B2 (en) * 1989-05-27 1999-11-10 住友化学工業株式会社 Poison bait for pest control
ZA903739B (en) * 1989-05-27 1991-03-27 Sumitomo Chemical Co A poison bait for control of noxious insects
DK0475902T3 (en) * 1990-09-10 1994-07-11 Sandoz Ltd Point source-insekticidindretning
US5396730A (en) * 1990-09-10 1995-03-14 Sandoz Ltd. Point source insecticide dispenser
JP2001288012A (en) * 2000-04-06 2001-10-16 Fumakilla Ltd Method for controlling insect pest
US20090239289A1 (en) * 2008-03-19 2009-09-24 Ipser Reid M Drain Foam Composition and Method of Using the Same

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1005821A (en) * 1971-02-01 1977-02-22 Clive A. Henrick 2,4-diolefinic compounds and the control of insects
US3752843A (en) * 1971-10-08 1973-08-14 Zoecon Corp Aliphatic di olefinic nitriles
JPS61152603A (en) * 1984-12-27 1986-07-11 Earth Chem Corp Ltd Transpiring agent for expelling cockroach

Also Published As

Publication number Publication date
NL8601134A (en) 1986-12-01
AU5733686A (en) 1986-11-20
SU1743330A3 (en) 1992-06-23
EG19057A (en) 1994-08-30
DE3615035A1 (en) 1986-11-13
GB2174908B (en) 1989-07-05
ATA125986A (en) 1990-03-15
FR2581508B1 (en) 1990-04-20
JPS61268602A (en) 1986-11-28
JPH0667801B2 (en) 1994-08-31
AT391242B (en) 1990-09-10
FR2581508A1 (en) 1986-11-14
AU589181B2 (en) 1989-10-05
CH667570A5 (en) 1988-10-31
BR8602190A (en) 1987-12-22
IE861246L (en) 1986-11-13
IE59071B1 (en) 1993-12-15
BE904740A (en) 1986-11-12
GB8611553D0 (en) 1986-06-18
DE3615035C2 (en) 1997-03-13
GB2174908A (en) 1986-11-19

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