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CA1225329A - Pest control device - Google Patents

Pest control device

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Publication number
CA1225329A
CA1225329A CA000470401A CA470401A CA1225329A CA 1225329 A CA1225329 A CA 1225329A CA 000470401 A CA000470401 A CA 000470401A CA 470401 A CA470401 A CA 470401A CA 1225329 A CA1225329 A CA 1225329A
Authority
CA
Canada
Prior art keywords
control device
pest control
cyano
chloro
phenoxybenzyl
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
Application number
CA000470401A
Other languages
French (fr)
Inventor
Robert C. Pearce
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
Priority to CA000470401A priority Critical patent/CA1225329A/en
Application granted granted Critical
Publication of CA1225329A publication Critical patent/CA1225329A/en
Expired legal-status Critical Current

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Abstract

NOVEL PEST CONTROL DEVICE

Abstract of the Disclosure A pest control device, such as an ear tag, for controlling pests such as flies, fleas and ticks on animals such as cattle and other livestock or pet animals which comprises a polymeric resin matrix and the pesticidally active compound .alpha.-cyano 3-phenoxybenzyl 2-(2-chloro-4-tri-fluoromethylanilino)-3-methylbutanoate.

Description

I

This invention relates Jo a method and a device for the effective and long-term control of harmful pests such as flies, fleas and ticks on cattle and other livestock or pet animals. sore particularly, it relates to a pest control device, in the form ox, for example, an ear tag, which comprises a polymeric resin matrix and the pesticidally active compound cyano-3-phenoxyben~yl 2-~2-chloro-4-trifluoromethylanilino)-3-methylbutanoate.
Livestock can be greatly troubled by pests such as Lo horn lies race flies, Gulf Coast ticks, spoons ear tics, etc., which can cause not only irritation to the animal and interference with it normal feeding and grazing habits but also oftentimes infection and illness.
A recently developed method for controlling pests on livestock it bayed on slow release pesticidal generators, which can be prepared by mixing a partie~lar pesticide with a resinous subset e which releases the pesticide over an extended period ox tire. Such pesticidal generators are described, for example, in US. Patent No 3,318,~69, .20 3,852l416 and 3,944,662. In particular, pest control devices attachable to the cars of livestock utilizing slow-release pesticide technology are disclosed in US. Patent Nos.
3,765,200 and 3,942,480, which describe use of 2,2-dichloro-vinyl dim ethyl phosphate ~DDVP) or repelling ticks; US.
Patent ~,195,075, describing ~-cyano-3-ph~noxybenzyl issue-propyl-4-chlorophenylacetate ~fen~alerate) or the control of Lowe and tic and US. Patent 4,265,876, describing 3-ph~noxy~enzyl dimly (2j2~dichlo~ovinyl~cyclopro-paneca~boxylata (perm~thri~ and ~cyano-3-phenoxybenzyl
2, 2-dlm0thyl-3- ( I, 2 -dichloro~i~yl) cyc:loprop~neca~xylate or controlling flies and tick ~53;~

The pesticide which is utilized in the-method and device of the present invention is ~-cyano-3-phenoxybenzyl 2-(2-chloro-4-trifluoromethylanillno)-3-methylbutaAnita, also known by the common name "fluvalinate," which con 5 exist in a number of stereoisomeric forms. Accordingly, the invention includes a single stereo isomer or a combination of two or more stereo isomers of the pesticidally-active compound. A preferred embodiment of the present invention utilizes US -cyano-3-phenoxybenzyl(R)-2-(2-chloro-4-tri~luoromethylanilino)-3-methylbutanoate. Fluvalinate and its preparation are disclosed in US. Patent 4,243,819. The preferred diastereomeric pair and its preparation are disk closed in US. Patent 4,260,633.
The active ingredient ~-cyano-3-phenoxybenzyl 2-(2-chloro-4-trifluoromethylanilino)-3-methylbutanoatee is present in the pest control device in a pesticidally effective amount, generally from about 1% to about 20% by weight of the total composition. Concentrations of about 2% to about 10~ by weight are preferred.
The pest control device of the present invention comprises the aforesaid poetized dispersed in a polymeric resin matrix. The polymeric resin matrix is comprised of a polymeric resin and, optionally, a suitable plasticizer.
In general, any thermoplastic or thermosetting resin, including elastomers, compatible with the pesticide is suitable as the polymeric resin. The resin needs to have adequate strength and sufficient durability to withstand normal wear. Further, the resin must be one which will permit adequate release of the pesticide. Examples of suitable substances are polyol~ins (for example, _ 3 ~2,~S3~

polyethylene and polypropylene); polyacrylates two example polymers and copolymers of methyl acrylate, ethyl acryla~e and methyl methacrylate); polymers of vinyl compounds (for example, polystyrene), polyvinyl halides for example polyvinyl chloride), polyvinyl acetals (for employ polyvinyl bitterly; polyvinylidene compounds (for example, polyvinylidene chloride); synthetic and natural elastomers (for example, hove brasiliensis, cesspools-prone, polybutadiene and SIR rubber; urea formaldehyde and melamine-formaldehyd~ resins; epoxy resins (for example, polymers of polyglycidyi ethers of polyhydric phenols);
cellulose plastics (for example, cellulose acetate and cell-lose bitterroot); and polyurethane. Generally, the polymeric resin comprises from about 35% to about 75% by weight of the total composition, with amounts ox from about 40% to about 70~ by weight being preferred.
Because one embodiment of the pesticide control device ox the present invention is an ear tag for attachment to cattle and other livestock, the polymer rosin material should be sufficiently strong yet flexible for this purpose.
Thus, Optionally plasticized thermoplastic resins are pro-furred as the polymer resin matrix. Suitable thermoplastic resins are polyvinyl resins such as polyvinyl halides including polyvinyl chloride, PVC), polyvinyl esters, polyp vinylidine chloride and chlorinated polyethylene. Plasticizers which may be employed to plasticize the thenmopla~tic resins include eater of pullback acids such as phthalate eater (fur example ductile phthalate, diphenyl foliate and dicyclohexyl phthalate), s~bacate eater (for example, dlpentyl subacute, n-butylbenzyl subacute and dibenzyl ~ebacate), ~2~S329 I, adipate esters (or example, ductile adipate, dicapryl adipate and di-isobutyl adipate) and citrate esters The particular plasticizer employed will depend upon its compatibility with the pesticide and with the particular resin used. The plastic cider must be one which will not exude from the particular resinate normal temperatures and conditions. In general, the plastic-zero comprises from 09~ to about 45% by weight of the total combo-session, with amounts of from about 25% to about 40% being preferred.
When the device of the present invention is in the form of an ear tag, polyvinyl chloride plasticized with ductile adipate, ductile phthalate or bottle bouncily phthala-te is the preferred polymeric resin matrix.
Other ingredients such as stabilizers, impact modifiers, dyes, fillers, anti-oxidants, secondary plasticizers, insect attract ants and other pesticides can be incorporated into the pest control device of the present invention, usually in amounts of 1 % or less to about 15% by weight of the total composition.
See Sears & Derby, The Technology of Plasticizers (John 20 Wiley & Sons, 1982) for a description of said other ingredients and plasticizers.
The pest control device of the present invention can be prepared by a variety of means depending on the polymeric resin matrix used. Suitable means of preparation include, for example, forming a dry blend of a thermoplastic resin, plasticizer and pesticide and using sufficient mixing and heat to obtain a homogeneous melt which can be cast, extruded or injection molded into a desired shape such as ear tags, bands collars, bars, or the like. Another method of preparation is to disperse the pesticide into the ingredients of a thermos setting composition, which composition is subsequently shaped and cured.

'I

~2~3~

he present invention includes within its scope a method of controlling pests such as flies, fleas and ticks on or in the very near vicinity of cattle and other livestock or pet animals which comprises attaching to the animal a polymeric resin matrix containing a pesticidally effective amount of -cyan 3-phenoxy~enzyl 2-(2 chloro-4-trifluoromethylanilino)-
3-methylbutanoate. One embodiment of the device is an ear tag for attaching to the ear of the animal, which tag can take the form of a single element, one end of which is capable of piercing the ear, or of a two-piece tag, based on clamps, pins or studs. Representatives of suitable tags are described in US. Patent Nos. 3,260,007, 3,388,492, 3,512,289, 3,595,201, 3,731,414 and 3,934,368.
Other embodiments of the invention include bands which may be wrapped around and scoured to the base of the animal's ears or horns. The device of ale present invention is especially effective against pests such as the face fly and horn fly and, hence, locating the device on or in close proximity to the face/head of the animal is advantageous.
Attachment to the end ox the animals tail would likewise be advantageous since cattle and other livestock often swish their tails around the face and head to ward off flies and other pests.
The device of the present invention can be effectively employed as a collar, especially in the form of a strong, flexible polymer matrix such as PVC, polyurethane and the like. Alternatively, device in the Norm of a bar or band can he affixed to the regular collar of the animal. Alto, a device of the present invention in the Norm of a small ~2532~

strip may ye secured to the regular ear tag of the animal such as by stapling, gluing or riveting the strip to the ear tag. See US. Patent No. 3,811,413, 3,900,981~ 3,949,708,
4,059,074, 4,184,452 and 4,366,777 for examples of collar do tag devices.

The hollowing examples are provided to illustrate the practice of the present invention. Temperature is in degrees Fahrenheit. "RUT" means room temperature The term "ow" indicates percentage by weight of the total composition.

I

EXAMPr~ 1 Polyvinyl chloride (PVC~ powder (wow, 1116.0 g) is mixed in a high intensity mixer (Herschel) until the polymer reaches 140. To this is added, with mixing, wow S (55.2 g) of epoxidized soybean oil, wow (664.8 g) of ductile phthalate, wow (55.2 g) of a PVC stabilizer and wow (S04.0 g) of rac~mic ~-cyano-3-phenoxybenzyl 2-(2-chloro-4-trifluoromethylanilino)-3-~ethylbutanoatee. The blend is heated to 175, with mixing, after which wow (4.8 g) of Starkey acid is slowly added and the temperature is ruptured to 17S. After a homogeneous blend is obtained, it is then cooled to RUT.
The blend is Ted into an injection molding machine, where it is heated (front zone, 150 center Noah 250;
lo nozzle, 320) and injection molded into dies to yield ear tags containing wow of ~-cyano-3-phenoxybenzyl sheller-4-trifluoromethylanilino)-3-methylbu~anoate.
the epoxidized soybean oil is 2-ethylhexyl epoxytallate, known as Drape 4.4, Argus Chemical Company.
The stabilizer is barium-zinc-phosphite stabilizer, Mark 160~ Argue Chemical Company.
The polyvinyl chloride is chosen from ethyl SM250~
(Ethyl Corporation), Ox 9400~(0ccidental Chemical Corporation) and Tenneco 250- (Tenneco).

To wow (1087.1 g) of PVC is added, with mixing, Ooze tll.45 g) ox phthalo blue and wow 145.8 g) of derailed yellow. The blend is heated to 150 with mixing.

So A premix of wow (199.9 g) of US ~-cyano-3-phenoxy-bouncily(R)-2-(2-chloro-4-tri~luoromethylanilino)-3-methyll-butanoate (91.6~ AYE.) and wow (114.5 g) of utile Bunnell phthalate is added to the blend as mixing is continued, followed by the addition of wow (91.6 g) of a PVC stabilizer (barium-zinc) and wow (732.8 g) of ductile phthalate. The resulting blend is heated to 185, wow (45.8 g) of Starkey acid is added, and the temperature is raised to 190. The blend is then cooled to RUT.
The blend is fed into an injection-molder, is heated (front zone, 340; center zone, 340; rear zone, 320; nozzle, 75) and it molded to yield ear tags containing wow of US
~-cyano-3-phenoxybenzyl (R)-(2-chloro-4-trifluoromethyl-anilino)-3-methylbutanoate.
Following the above procedure, the compositions a, b, c, d and e, given in Table I below, are prepared to yield ear tags containing, respectively, low, wow, wow, wow and wow ox US -cyano-3-phenoxybenzyl (R)-2-(2-chloro-4-tri-fluoromethylanilino)-3-methylbutanoate.

g TABLE I
.. . . .. _ _ , C o m p o s i t i o ayatollah a b c d e p~lyvlnyl chlorlde47.47 1/ 47.47 47.47 ~7.47 47.47 phthalo blue 0.50 0.50 0.50 0.50 0.50 dl~rylide yellow 2.00 2.00 2.00 2.00 2.00 pesticide 2/ 10.92 8.73 6.55 4.50 2.25 bottle bouncily phthalate 5.00 5.00 5.00 S.00 5.00 barlum-zinc stabilizer 4.00 4.00 4.00 4.00 4.00 ductile phthalate 29.81 32.00 34.18 36.23 38.48 Starkey acid 0.30 0.30 0.30 0.30 0.30 1/ amounts give in WOW.
2/ US -cya~o-3-phenoxybenzyl ~R)-2-(2-chloro-4-tr~fluoromethylanilino)-3-methylbutanoate (91.6% AYE.).

EXPl~PLE 3 PVC (Ethyl SM250; wow, 4360 g) is mixed and heated to 150. To this it added, with mixing, a premix of wow (320 g) ox a barium-~inc PVC stabilizer and wow (736 go of US -cyano-3-phenoxybenzyl (R~-2-(2-chloro-4-trifluoromethylanilino)-3-methylbutanoate (89.3% AYE.), hollowed by the addition of wow (2160 g) of ductile phthalate and wow (240 g) of burl bouncily phthalate. The resulting blend is heated, with mixing, to 185, after which wow (24 g) of Starkey acid is added, the temperature it raised to 190~ and wow (160 g) of orange dye I (PUS 82734 TUB) is added. The blend is mixed or one minute and it then cooled to RUT.

2S3Z~

The blend is fed into an injec~ion~molder, is heated (front zone, 340; center zone, 340; near zone, 320; nozzle, 285) and is molded to yield ear tags containing wow of US
-cyano-3-phenoxybenzyl (R)-2-(2-chloro-4-tri~luoromethyl-anilino)-3-methylbutanoate.

Claims (14)

Claims:
1. A pest control device for attachment to an animal which comprises a polymeric resin matrix having dispersed therein a pesticidally effective amount of the compound .alpha.-cyano-3-phenoxybenzyl 2-(2-chloro-4-trifluoromethylani-lino)-3-methylbutanoate.
2. A pest control device according to claim 1 where-in the polymeric resin matrix if desired is a plasticized thermoplastic resin.
3. A pest control device according to claim 2 where-in the thermoplastic resin is a polyvinyl halide resin.
4. A pest control device according to claim 3 where-in the plasticizer is selected from dioctyl adipate, dioctyl phthalate and butyl benzyl phthalate.
5. A pest control device according to claim 4 where-in the polyvinyl halide resin is polyvinyl chloride.
6. A pest control device according to claim 5 where-in the pesticide is (R,S)-.alpha.-cyano-3-phenoxybenzyl (R)-2-(2-chloro-4-trifluoromethylanilino)-3-methylbutanooate.
7. A pest control device according to claim 2 in the form of a tag which is attachable to the ear of cattle and other livestock.
8. A pest control device according to claim 7 where-in the thermoplastic resin is present in the amount of from about 35% to about 75% by weight of the total composition, the plasticizer is present in the amount of from 0% to about 45% by weight of the total composition and the pesticide is present in the amount of from about 1% to about 20% by weight of the total composition.
9. A pest control device according to Claim 8 wherein the thermoplastic resin is present in the amount of from about 40% to about 70% by weight of the total composition, the plasticizer is present in the amount of from about 25% to about 40% by weight of the composition and the pesticide is present in the amount of from about 2% to about 10% by weight of the total composition.
10. A pest control device according to Claim 9 wherein the thermoplastic resin is polyvinyl chloride.
11. A pest control device according to Claim 10 wherein the pesticide is (R,S)- .alpha.-cyano-3-phenoxybenzyl (R)-2-(2-chloro-4-trifluoromethylanilino)-3-methylbutanoate.
12. A method for controlling pests on animals which comprises attaching to said animal a polymeric resin matrix having dispersed therein a pesticidally effective amount of the compound .alpha.-cyano-3-phenoxybenzyl 2-(2-chloro-4-trifluoro-methylanilino)-3-methylbutanoate.
13. The method according to Claim 12 wherein the polymeric resin matrix is in the form of an ear tag and is attached to the ear of cattle and other livestock.
14. The method according to claim 13 wherein the pesticide is (R,S)-.alpha.-cyano-3-phenoxybenzyl (R)-2-(2-chloro-4-trifluoromethylanilino)-3-methylbutanoate.
CA000470401A 1984-12-18 1984-12-18 Pest control device Expired CA1225329A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA000470401A CA1225329A (en) 1984-12-18 1984-12-18 Pest control device

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CA000470401A CA1225329A (en) 1984-12-18 1984-12-18 Pest control device

Publications (1)

Publication Number Publication Date
CA1225329A true CA1225329A (en) 1987-08-11

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Family Applications (1)

Application Number Title Priority Date Filing Date
CA000470401A Expired CA1225329A (en) 1984-12-18 1984-12-18 Pest control device

Country Status (1)

Country Link
CA (1) CA1225329A (en)

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