CA1059025A - Cyclopropanecarboxylates for systemic control of ectoparasites - Google Patents
Cyclopropanecarboxylates for systemic control of ectoparasitesInfo
- Publication number
- CA1059025A CA1059025A CA243,228A CA243228A CA1059025A CA 1059025 A CA1059025 A CA 1059025A CA 243228 A CA243228 A CA 243228A CA 1059025 A CA1059025 A CA 1059025A
- Authority
- CA
- Canada
- Prior art keywords
- animal feed
- tick
- cyclopropanecarboxylates
- ectoparasites
- weight
- 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
Links
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/111—Aromatic compounds
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
TITLE: CYCLOPROPANECARBOXYLATES FOR
SYSTEMIC CONTROL OF ECTOPARASITES
ABSTRACT OF THE INVENTION
An animal feed composition comprising, a nutri-tionally balanced animal feed containing a cyclopropane-carboxylic acid of the formula:
SYSTEMIC CONTROL OF ECTOPARASITES
ABSTRACT OF THE INVENTION
An animal feed composition comprising, a nutri-tionally balanced animal feed containing a cyclopropane-carboxylic acid of the formula:
Description
25,643 ``` ~oS9~Z5 SU~ ~RY OF THE INVENTION
This invention relates to an animal feed composition comprising, a nutrionally balanced feed containing a cyclopropanecarboxylic acid of the formula:
R- ~ -CO-0-CH 2 l ~H3 O ~
wherein R is 2,2-dichlorovinyl- or 2-methyl-propenyl- in an amount of from 0.01% to 2.5~ by weight of the feed.
BAC~GR~UND OF THE INVENTION
1. Field of the Invention: The field of the invention is the use of cyclopropanecarboxylates for systemic control of ectoparasites on animals.
This invention relates to an animal feed composition comprising, a nutrionally balanced feed containing a cyclopropanecarboxylic acid of the formula:
R- ~ -CO-0-CH 2 l ~H3 O ~
wherein R is 2,2-dichlorovinyl- or 2-methyl-propenyl- in an amount of from 0.01% to 2.5~ by weight of the feed.
BAC~GR~UND OF THE INVENTION
1. Field of the Invention: The field of the invention is the use of cyclopropanecarboxylates for systemic control of ectoparasites on animals.
2. The Prior Art: Ixodidae, or hard ticks, are generally categorized as one-host, two-host or three-host ticks. They sustain themselves and their species by attach-ing to a host animal and feeding the blood and body fluids thereof. Engorged females drop from the host animal and lay their eggs (2,000 to 20,000) in a niche on the ground or in some sheltered area where hatching occurs. The larvae then seek a host from which to obtain a blood meal and depending on whether the tick is a one, two or three-host tick may drop off the host to molt.
Ixodid ticks are responsible for the transmission and propagation of a great many human and animal diseases throughout the world. Those ticks of major economic impor-tance include Boophilus spp., Rhipicephalus spp., Ixodes spp., Hyalomma spp., Amblyomma spp. and Dermacentor spp.
They are vectors for disease, tick paralysis and tick toxi-cosis. A single tick species can cause paralysis of several different mammals, and several tick species can cause pa-~' ~-', - 1 -1059~Z5 ralysis in a particular host. Tick-borne diseases, such as Sweating Sickness, Babesiosis, Anaplasmosis, Theileriosis and Heartwater, have been and are responsible for the death and/or debilitation of a vast number of animals throughout the world each year. Ticks are responsible for great eco-nomic losses in livestock production in the world today.
Such losses are, of course, attributable not only to death, but also to damaged hides, loss in growth rate, reduction in milk production and reduced grade of meat animals.
Although the debiiitating effects of tick and other pest infestation of animals has been recognized for years, and tremendous strides have been made in tick con-trol programs, no entirely satisfactory method for con-trolling or eradicating these parasites has been forth-coming. Topical treatment of tick-infested and other ecto-parasite plagued animals with chemical ectoparasital agents, such as the chlorinated hydrocarbons, including benzene hexachloride (BHC), DDT, toxaphene, chlordane and aldrin;
the organophosphorus compounds, including Delnav, ethion and coumaphos, have been partially successful in controlling ectoparasite populations. However, certain speeies of eeto-parasites have become resistant to the ehlorinated hydro-carbons and the organophosphates.
Netherlands Patent No. 7,307,130, issued Nov. 27, 1973, describes a broad class of cyclopropanecarboxylic acid ester derivatives which include the compounds I have found to be effective agalnst ectoparasites. The patentee does not, of course, suggest the systemic method of the present invention.
DETAILED DESCRIPTION
The invention provides a method for the systemic control of insecticidal and acaracidal agents which attack warm-blooded or homothermic animals by employing systemic z ~05911 ZS
cyclopropanecarboxylates that provide excellent control of ectoparasites. In the invention, cyclopropanecarboxylates of the formula:
ClzC=CH-\ > co-o-c~24 CH3- ,H3 0 ~
Cyclopropanecarboxylic acid,
Ixodid ticks are responsible for the transmission and propagation of a great many human and animal diseases throughout the world. Those ticks of major economic impor-tance include Boophilus spp., Rhipicephalus spp., Ixodes spp., Hyalomma spp., Amblyomma spp. and Dermacentor spp.
They are vectors for disease, tick paralysis and tick toxi-cosis. A single tick species can cause paralysis of several different mammals, and several tick species can cause pa-~' ~-', - 1 -1059~Z5 ralysis in a particular host. Tick-borne diseases, such as Sweating Sickness, Babesiosis, Anaplasmosis, Theileriosis and Heartwater, have been and are responsible for the death and/or debilitation of a vast number of animals throughout the world each year. Ticks are responsible for great eco-nomic losses in livestock production in the world today.
Such losses are, of course, attributable not only to death, but also to damaged hides, loss in growth rate, reduction in milk production and reduced grade of meat animals.
Although the debiiitating effects of tick and other pest infestation of animals has been recognized for years, and tremendous strides have been made in tick con-trol programs, no entirely satisfactory method for con-trolling or eradicating these parasites has been forth-coming. Topical treatment of tick-infested and other ecto-parasite plagued animals with chemical ectoparasital agents, such as the chlorinated hydrocarbons, including benzene hexachloride (BHC), DDT, toxaphene, chlordane and aldrin;
the organophosphorus compounds, including Delnav, ethion and coumaphos, have been partially successful in controlling ectoparasite populations. However, certain speeies of eeto-parasites have become resistant to the ehlorinated hydro-carbons and the organophosphates.
Netherlands Patent No. 7,307,130, issued Nov. 27, 1973, describes a broad class of cyclopropanecarboxylic acid ester derivatives which include the compounds I have found to be effective agalnst ectoparasites. The patentee does not, of course, suggest the systemic method of the present invention.
DETAILED DESCRIPTION
The invention provides a method for the systemic control of insecticidal and acaracidal agents which attack warm-blooded or homothermic animals by employing systemic z ~05911 ZS
cyclopropanecarboxylates that provide excellent control of ectoparasites. In the invention, cyclopropanecarboxylates of the formula:
ClzC=CH-\ > co-o-c~24 CH3- ,H3 0 ~
Cyclopropanecarboxylic acid,
3-(2,2-dichlorovinyl)-2,2-dimethyl-m-phenoxybenzyl ester, cis and trans isomer (GH3)2C=CH- ~ r--~
> -C0-0-CH 2 y \>
or CH3 ~
Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-propenyl)-3'-phenoxybenzyl ester, c1s and trans isomer are administered to the animals orally or parenterally in amounts ranging from 0.01 to about 600 mg per kilogram animal body weight and preferably from about 100 mg to 400 mg per kilogram animal body weight.
As indicated above, the systemic insecticidal and acaricidal agents of the invention may be administered orally or parenterally. When given orally, they may be in any convenient oral form of medication, such as a capsule, tablet or as an oral drench.
The agents may also be incorporated in a nu-tritionally balanced animal feed in the range of 0.01% to 2.5~ by weight of feed and preferably 0.01% to 1.0% by weight of feed. They may also be added to the animal drlnking water with the aid of a pharmaceutically acceptable dispersing or emulsifying agent.
- 30 If desired, the systemic agents may be intro-duced into the body of the animal by subcutaneous, intra-1059~25 muscular or intraperitoneal injection. The manner of admin-istration of the systemic agents is not particularly important, so long as the prescribed amounts of systemic agents are introduced into the body of the animal where it may be distributed by the action of the circulatory system.
Advantageously, the above-identified compounds are highly effective systemic ixodicidal agents. They have re-latively low mammalian toxicity and are effective for pro-tecting animals, particularly dom~stic and farm animals, such as dogs, cats, cattle, sheep, horses and the like, from attack by ticks. They can be used to control a wide variety of ixodid ticks, including Boophilus spp., Amblyomma spp., Rhipicephalus ~., Dermacentor ~., and Hyalomma spp .
The invention is exemplified by the following non-limiting examples.
Example l _etermination of Systemic Ixodicidal Activity of Cyclopro-panecarboxylic acid, 3-(2,2-dichlorovinyl)-2,2-dimethyl-m-phenoxybenzyl ester (mixture of cis- trans isomers) Against the three-host tick Rhipicephalus anguineus Albino guinea pigs are housed individually and fed guinea pig chow and water ad libitum. One leaf of cab-bage per day is also given to each guinea pig.
The diet employed in these tests is as follows:
Crude protein not less than 18.0%
Crude fat not less than4.0%
Crude fiber not more than16.0%
Added minerals not more than 3.5%
Ash not more than 7.0%
and consists of the following ingredients: Ground wheat, ground yellow corn, drled skimmed milk, soybean meal, de-hydrated alfalfa meal, cane molasses, wheat middlings, -1059~Z5 animal fat preserved with BHA, vitamin B12 supplement, riboflavin supplement, cholin chloride, calcium pantothe-nate, thiamin, niacin, folic acid, ascorbic acid, vitamin A
supplement, D activated sterol (source of vitamin D3), methionine hydroxy analogue calcium, pyridoxine hydrochloride, vitamin E supplement, dicalcium phosphate, calcium carbonate, iodized salt, copper oxide, copper sulfate, iron sulfate, iron oxide, manganous oxide, cobalt carbonate, zinc oxide.
To the shaved back of each guinea pig, a capsule made from a 2 inch spud gasket, with the base ground down to provide greater flexibility, is glued using 3M adhesive no. 8001. Five male and five female adult Rhipicephalus sanguineus ticks are placed inside the capsule and allowed to attach to the guinea pig. A gauze material is fastened over the top of the gasket to prevent the ticks from escaping.
The yuinea pigs are given a daily oral dose by gelatin capsule of either 400 or 100 mg per kilogram body weight of the test compound. The ticks do not appear to be affected for about 3 days after the initial treatment except for slight color changes and some reduction in size, but become moribund and die shortly thereafter. The following test data are obtained:
~Tick Daily oral dose (mg/kg) Mortality control 0 Example 2 Determination of ~ystemic Ixodicidal Activity of Cyclopro-30 panecarboxylic acid, 3-(2,2-dichlorovinyl)-2,2-dimethyl-, . . .
m-phenoxybenzyl ester, cis -trans (23% - 77%) against the ~ .... _ . ...
Three-host Tick Dermacentor variabilis.
_ By the method of Example 1 the efficacy of the test compound for controlling the above-identified tick species is demonstrated. The Dermacentor variabilis ticks are somewhat less susceptible to the test compound and after about 5 days become moribund and die shortly thereafter.
The data obtained are as follows:
% Tick Daily oral dose (mg/kg) Mortality Control 0 Results comparable to those in the Examples are obtained with the ixodicide, cyclopropanecarboxylic acid, 2,2-di-methyl-3-(2-methylpropenyl)-3-phenoxybenzyl ester, trans and cls.
~ .
> -C0-0-CH 2 y \>
or CH3 ~
Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-propenyl)-3'-phenoxybenzyl ester, c1s and trans isomer are administered to the animals orally or parenterally in amounts ranging from 0.01 to about 600 mg per kilogram animal body weight and preferably from about 100 mg to 400 mg per kilogram animal body weight.
As indicated above, the systemic insecticidal and acaricidal agents of the invention may be administered orally or parenterally. When given orally, they may be in any convenient oral form of medication, such as a capsule, tablet or as an oral drench.
The agents may also be incorporated in a nu-tritionally balanced animal feed in the range of 0.01% to 2.5~ by weight of feed and preferably 0.01% to 1.0% by weight of feed. They may also be added to the animal drlnking water with the aid of a pharmaceutically acceptable dispersing or emulsifying agent.
- 30 If desired, the systemic agents may be intro-duced into the body of the animal by subcutaneous, intra-1059~25 muscular or intraperitoneal injection. The manner of admin-istration of the systemic agents is not particularly important, so long as the prescribed amounts of systemic agents are introduced into the body of the animal where it may be distributed by the action of the circulatory system.
Advantageously, the above-identified compounds are highly effective systemic ixodicidal agents. They have re-latively low mammalian toxicity and are effective for pro-tecting animals, particularly dom~stic and farm animals, such as dogs, cats, cattle, sheep, horses and the like, from attack by ticks. They can be used to control a wide variety of ixodid ticks, including Boophilus spp., Amblyomma spp., Rhipicephalus ~., Dermacentor ~., and Hyalomma spp .
The invention is exemplified by the following non-limiting examples.
Example l _etermination of Systemic Ixodicidal Activity of Cyclopro-panecarboxylic acid, 3-(2,2-dichlorovinyl)-2,2-dimethyl-m-phenoxybenzyl ester (mixture of cis- trans isomers) Against the three-host tick Rhipicephalus anguineus Albino guinea pigs are housed individually and fed guinea pig chow and water ad libitum. One leaf of cab-bage per day is also given to each guinea pig.
The diet employed in these tests is as follows:
Crude protein not less than 18.0%
Crude fat not less than4.0%
Crude fiber not more than16.0%
Added minerals not more than 3.5%
Ash not more than 7.0%
and consists of the following ingredients: Ground wheat, ground yellow corn, drled skimmed milk, soybean meal, de-hydrated alfalfa meal, cane molasses, wheat middlings, -1059~Z5 animal fat preserved with BHA, vitamin B12 supplement, riboflavin supplement, cholin chloride, calcium pantothe-nate, thiamin, niacin, folic acid, ascorbic acid, vitamin A
supplement, D activated sterol (source of vitamin D3), methionine hydroxy analogue calcium, pyridoxine hydrochloride, vitamin E supplement, dicalcium phosphate, calcium carbonate, iodized salt, copper oxide, copper sulfate, iron sulfate, iron oxide, manganous oxide, cobalt carbonate, zinc oxide.
To the shaved back of each guinea pig, a capsule made from a 2 inch spud gasket, with the base ground down to provide greater flexibility, is glued using 3M adhesive no. 8001. Five male and five female adult Rhipicephalus sanguineus ticks are placed inside the capsule and allowed to attach to the guinea pig. A gauze material is fastened over the top of the gasket to prevent the ticks from escaping.
The yuinea pigs are given a daily oral dose by gelatin capsule of either 400 or 100 mg per kilogram body weight of the test compound. The ticks do not appear to be affected for about 3 days after the initial treatment except for slight color changes and some reduction in size, but become moribund and die shortly thereafter. The following test data are obtained:
~Tick Daily oral dose (mg/kg) Mortality control 0 Example 2 Determination of ~ystemic Ixodicidal Activity of Cyclopro-30 panecarboxylic acid, 3-(2,2-dichlorovinyl)-2,2-dimethyl-, . . .
m-phenoxybenzyl ester, cis -trans (23% - 77%) against the ~ .... _ . ...
Three-host Tick Dermacentor variabilis.
_ By the method of Example 1 the efficacy of the test compound for controlling the above-identified tick species is demonstrated. The Dermacentor variabilis ticks are somewhat less susceptible to the test compound and after about 5 days become moribund and die shortly thereafter.
The data obtained are as follows:
% Tick Daily oral dose (mg/kg) Mortality Control 0 Results comparable to those in the Examples are obtained with the ixodicide, cyclopropanecarboxylic acid, 2,2-di-methyl-3-(2-methylpropenyl)-3-phenoxybenzyl ester, trans and cls.
~ .
Claims (3)
1. An animal feed composition comprising, a nutritionally balanced animal feed containing a cyclopro-panecarboxylic acid of the formula:
wherein R is 2,2-dichlorovinyl- or 2-methyl-propenyl- in an amount of from 0.01% to 2.5% by weight of the feed.
wherein R is 2,2-dichlorovinyl- or 2-methyl-propenyl- in an amount of from 0.01% to 2.5% by weight of the feed.
2. An animal feed composition according to Claim 1 comprising, a nutritionally balanced animal feed containing cyclopropanecarboxylic acid, 3-(2,2-dichloro-vinyl)-2,2-dimethyl-m-phenoxybenzyl ester cis - trans isomers thereof in an amount of from 0.01% to 1.0% by weight of the feed.
3. An animal feed composition according to Claim 1 comprising a nutritionally balanced animal feed containing cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-propenyl)-3-phenoxybenzyl ester cis - trans isomers thereof in an amount of from 0.01% to 1.0% by weight of the feed.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55010775A | 1975-02-13 | 1975-02-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1059025A true CA1059025A (en) | 1979-07-24 |
Family
ID=24195777
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA243,228A Expired CA1059025A (en) | 1975-02-13 | 1976-01-08 | Cyclopropanecarboxylates for systemic control of ectoparasites |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS51110036A (en) |
| AU (1) | AU505678B2 (en) |
| CA (1) | CA1059025A (en) |
| DE (1) | DE2601743A1 (en) |
| FR (1) | FR2300553A1 (en) |
| GB (1) | GB1534527A (en) |
| IT (1) | IT1053419B (en) |
| NL (1) | NL7600798A (en) |
| NZ (1) | NZ179683A (en) |
| ZA (1) | ZA757985B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2341307A1 (en) * | 1976-02-19 | 1977-09-16 | Roussel Uclaf | PYRETHRINOIDS FOR MEDICINAL PRODUCTS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
| CA1117005A (en) * | 1978-03-07 | 1982-01-26 | Patrick G. Feakins | Animal ear-tags, their manufacture and their use |
| FR2471187A1 (en) * | 1979-12-10 | 1981-06-19 | Roussel Uclaf | NEW COMPOSITIONS FOR THE CONTROL OF PARASITES OF HOT-BLOOD ANIMALS |
| FR2470601A1 (en) * | 1979-12-04 | 1981-06-12 | Roussel Uclaf | Acaricidal alpha-cyano 3-phenoxy-benzyl ester compsns. - esp. ester(s) with cis 2,2-di:methyl-3-2,2-di:chloro:vinyl-cyclopropyl-1-carboxylate or alpha-isopropyl phenylacetic acids |
| FR2470602A1 (en) * | 1979-12-04 | 1981-06-12 | Roussel Uclaf | Acaricidal compsn. for control of animal ticks and mites - contains (s)-alpha-cyano 3-phenoxy-benzyl 1R, cis-2,2-di:methyl-3-2,2-di:chloro:vinyl-cyclopropane-1-carboxylate |
| US5286749A (en) * | 1980-11-21 | 1994-02-15 | Pitman-Moore Inc. | Control of sheep ectoparasites |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1511646A (en) * | 1974-05-08 | 1978-05-24 | Wellcome Found | Method for insecticide use |
-
1975
- 1975-12-23 ZA ZA00757985A patent/ZA757985B/en unknown
- 1975-12-24 GB GB52890/75A patent/GB1534527A/en not_active Expired
- 1975-12-24 AU AU87868/75A patent/AU505678B2/en not_active Expired
-
1976
- 1976-01-06 NZ NZ179683A patent/NZ179683A/en unknown
- 1976-01-08 CA CA243,228A patent/CA1059025A/en not_active Expired
- 1976-01-19 DE DE19762601743 patent/DE2601743A1/en not_active Withdrawn
- 1976-01-22 IT IT47753/76A patent/IT1053419B/en active
- 1976-01-27 NL NL7600798A patent/NL7600798A/en not_active Application Discontinuation
- 1976-02-12 FR FR7603877A patent/FR2300553A1/en active Granted
- 1976-02-12 JP JP51013337A patent/JPS51110036A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS51110036A (en) | 1976-09-29 |
| AU8786875A (en) | 1977-06-30 |
| IT1053419B (en) | 1981-08-31 |
| FR2300553B1 (en) | 1979-09-28 |
| GB1534527A (en) | 1978-12-06 |
| ZA757985B (en) | 1976-12-29 |
| FR2300553A1 (en) | 1976-09-10 |
| NZ179683A (en) | 1978-04-28 |
| DE2601743A1 (en) | 1976-08-26 |
| AU505678B2 (en) | 1979-11-29 |
| NL7600798A (en) | 1976-08-17 |
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