GB2147808A - Controlling nematodes in soil or animals - Google Patents
Controlling nematodes in soil or animals Download PDFInfo
- Publication number
- GB2147808A GB2147808A GB08426115A GB8426115A GB2147808A GB 2147808 A GB2147808 A GB 2147808A GB 08426115 A GB08426115 A GB 08426115A GB 8426115 A GB8426115 A GB 8426115A GB 2147808 A GB2147808 A GB 2147808A
- Authority
- GB
- United Kingdom
- Prior art keywords
- antibiotic
- soil
- nematodes
- animals
- fermentation broth
- 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.)
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/01—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing oxygen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12N1/20—Bacteria; Culture media therefor
- C12N1/205—Bacterial isolates
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/44—Preparation of O-glycosides, e.g. glucosides
- C12P19/60—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
- C12R2001/03—Actinomadura
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biochemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- General Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Microbiology (AREA)
- Biomedical Technology (AREA)
- Molecular Biology (AREA)
- Virology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Antibiotic LL-C23024 alpha , or a pharmaceutically acceptable salt thereof, or a fermentation broth or harvest mash solid from which the antibiotic is obtained, is used to control nematodes in warm-blooded animals or in the soil.
Description
1 GB 2 147 808 A 1
SPECIFICATION
Use of antibiotic LL-C23024 a in controlling nematodes This invention relates to the use of the antibiotic LL-C23024 in controlling nematodes. The present application is divided out of our co- pending Application No. 8225339 (Publication No. 2108113A). The antibiotic LL-C23024 a has the following structure:
0Me Meo,, 10 e 0Me 0 Me Me Me Me m iiii,Me 0 0 0 H H H 0 M1 e H 0 M= e H= 0 H H OH H Me The antibiotic LL-C23024 a may be obtained by aerobically fermenting Actinomadura yumaense sp. nov.
or a mutant thereof in a liquid medium containing assimilable sources of carbon, nitrogen and inorganic salts, until substantial antibiotic activity is imparted to the fermentation broth, as describea in greater detail in the parent application, supra.
The antibiotic LL-C23024 a identical to the antibiotic designated X-1 4868A in U.S. -A-4278663 assigned to Hoff man-La Roche Inc which issued on 14-07-81. This prior U.S. patent discloses that antibiotic X-1 4868A is active against the growth of certain gram-positive bacteria, possesses anticoccidiostatic activity eg when administered to fowl such as turkeys and chickens, can be used as a growth promotant in ruminant animals such as cattle, thereby also preventing and treating ketosis in such animals, and, finally, has demonstrated activity in the treatment or prevention of swine dysentery.
The present invention is based on our discovery that antibiotic LL-C23024 at exhibits activity as a nematocidal agent. As is well known (see eg Webster's Third New International Dictionary, 1971), nematodes may be parasites of warm- blooded animals of free-living dwellers in soil.
The following tests demonstrate the nematocidal activity of antibiotic LLC23024 a.
ExampleA
Evaluation of test compositions for nematocidal activity using the freeliving Hermaphroditic microbivorous 40 nematode Caenorhabditis elegans 11 In the following tests, C. elegans is used to determine the nematocidal activity of the fermentation broth and the harvest mash containing antibiotic LL-C23024 a and prepared by the procedures taught in the parent application. This organism is also used to evaluate LL-C23024 a to determine the nematocidal activity thereof.
In these tests, fermentation broth is the fermentation liquid and solids mixture taken before the solids, i.e., the harvest mash, is separated from the liquid. Harvest mash is the solids remaining after separation.
For evaluation of harvest mash, the harvest mash solids are dispersed 1: 1 in distilled water. The fermentation broth is used as is and contains both liquid and solids.
In the present evaluations, C. elegans is maintained in a C. briggsae Maintenance Medium. The Maintenance Medium is commercially available from Grant Island Biological Company, Grant Island, New York, and has the following compositions:
C. briggsae MAINTENANCE MEDIUM (1) so Component mg1L INORGANIC SALTS CaC12 - 2H20 220.50 CUC12 - 2H20 6.50 60 Fe(NH4)2 (S04)2 - 6H20 58.80 KH2PO4 1225.50 KOH (a) MnC12-4H2O 22.20 ZnC12 10.20 65 2 GB 2 147 808 A 2 OTHER COMPONENTS N-Acetyiglucosamine 15.00 Adenosine-3'-W)-phosphoric acid.H20 365.00 Cytidine-3'-(2')-phosphoric acid 323.00 5 D-Glucose 1315.00 Glutathione, reduced 204.00 Guanosine-X-W)-P041\1a2-H20 363.00 Magnesium citrate.5H20 (Dibasic) 915.00 Potassium citrate.H20 486.00 10 DL-Thioctic acid 3.75 Thymine 126.00 Uridine-X-(2')-phosophoric acid 324.00 AMINOACIDS 15 L-Alanine 1395.00 L-Arginine 975.00 L-Aspartic acid 1620.00 L-Cysteine I-IC1.1---12028.00 20 L-Glutamate (Na).H20 550.00 L-Glutamine 1463.00 Glycine 722.00 L-Histidine 283.00 L-Isoleucine 861.00 25 L-Leucine 1439.00 L-Lysine HCI 1283.00 L-Methionine 389.00 L-Phenylalanine 803.00 L-Proline 653.00 30 L-Serine 788.00 L-Threonine 717.00 L-Tryptophan 184.00 L-Tyrosine 272.00 L-Valine 1020.00 35 VITAMINS P-aminobenzoic acid 7.50 Biotin 3.75 40 Choline dihydrogen citrate 88.50 Cyanocobalamine (B 12) 3.75 Folinate (Ca) 3.75 Myo-inositol 64.50 Niacin 7.50 45 Niacinamide 7.50 Pantethine 3.75 Pantothenate (Ca) 7.50 Pterolyglutamic acid 7.50 Pyridoxal phosphate 3.75 50 Pyridoxa mine 21-IC1 3.75 Pyridoxine HCI 7.50 Riboflavin-5'-P04(Na)-2H20 7.50 Thiamine HCI 7.50 References: (1) Hansen, E. L, Proc. Soc. Exp. Bio. & Med. 121: 30-393 (1966). Remarks:
(a) As needed for adjustment to pH 5.9 + 0.1.
3 GB 2 147 808 A 3 A well plate having a series of smal I wells is used for the eva I uations.Twenty-five m I of fermentation broth, 1:1 water/harvest mash suspension, or an aqueous/acetone solution of LL-C230vacontainingfrom 31. 25 to 500 ppm of test compound, is asceptically deposited in separate wells. To each well is then added 25 mi of the C. elegans maintenance medium containing 10-20 adult worms plus larvae of various ages plus eggs. The plates are then placed in a hood and examined at 48 hours post- inoculation to assess the speed and degree of nematocidal activity of the test compositions. Data obtained are reported below. Where activity is observed forthe fermentation broth, said broth is further diluted to provide a 1:4 broth to C. elegans ratio.
TABLE V11 10
Concentration ppm or Nematocidal Activity Composition Dilution at 48 hours Fermentation Broth D=1:1 8 (no motility) D=1:4 20 Harvest Mash LL-23024 @ 500 ppm 7 250 13pm 7 ppm 7 62.5 ppm 6 25 31.25 ppm 0 The activity legend employed in these evaluations is as follows:
Activitylegend 8 = No Motility (Apparent Death) 7 = Markedly Reduced Motility 6 = Reduced Motility 0 = Normal Motility for Species Example 8
Evaluation of LLC23024 (x as a nematocidal agent against infective larvae of ruminant nematodes Evaluation of LL-C23024 a as a nematocidal agent against the infective larvae of ruminant nematodes:
Haemonhmus contortus, Ostertagia circumcincta, Trichostrongylus axei, T. Colubriformis; and against the vinegar eel worm, Turbatrix acetiwas determined using the above-mentioned nematode species were 40 substituted for C. elegans.
Data obtained are reported in the Table below.
Third Stage Sheathed Larvae.
TA BL E VIII 45 In Vitro' Concentration of =- LL-C23024a ActivityAgainst (at48Hours) 50 ppm H. Contort. 0. Circum. T. Axei T. Colub. T. Aceti 500 8 8 b 8 b 8 6 250 7 8b 8 b 7 6 125 7 7 7 6 7 55 625 7 6 7 6 6 31.25 6 6 0 6 6 0 (Control) 0 0 0 0 0 aConducted in 96-well tissue culture plates, prepared in double-distilled water: 25 Ll of LL-C23024 9, solution and 25 jil of nematode culture were added perwell.
4 GB 2 147 808 A Activity Legend.. 8 = No Motility (Apparent Death) 7 = Markedly Reduced Motility 6 = Reduced Motility 0 = Normal Motility for Species bWithin 24 hours 4 Example C
Evaluation of nematocidal activity of antibiotic LL-C23024 u. against Nematospiroides dubius andAspicularis 10 tetraptera in mice In the following tests, Swiss-Webster female white mice are infected with Namatospiroides dubius and Aspicularis tetraptera and held for three weeks to permit the infections to mature.
Afterthe holding period, the mice are randomly divided into groups of four, and the groups placed in separate cages. Medicated feeds containing from about 31.25 ppm to 4,000 ppm of test compound are then 15 offered adlibitum to the mice for one week. Water is also provided adlibitum throughout the test period. During the treatment period, the mouse droppings are examined to determine whether worms are being passed. All treatment groups were found to be passing worms, thus indicating nematocidal activity at all compound concentrations against both nematodes. Atthe end of the one-week medicated feed treatment, the mice are necropsied, and the contents of the intestinal tracts thereof examined forworms. Data obtained 20 are reported below as percent reduction of worms as compared with infected, unmedicated controls.
In these tests, crude fermentation broths obtained before harvest of the mash, and containing from 1,000 ppm to 4,000 ppm of the nematocidal antibiotic were evaluated. Also evaluated was mouse feed treated with from 31.25 ppm to 500 ppm of LL-C23024 9_ dissolved in an acetonelwater 1: 1 mixture.
Activity MG Reduction) Test Dietary Against Composition conc. ppm N.dubius A. tetraptera 30 Fermenta tion Broth 4,000 73 - with LL-C23034a 2,000 44 53 LL-C23024a 1,000 65 33 500 70 SA' 35 250 63 SA 61 SA 62.5 29 SA 31.25 32 SA 40 Amount of LL-C23024u- undetermined Slight activity: Increased number of pinworms recovered in fecal examination Compared to infected unmedicated controls The above examples show that antibiotic LL-C23024 a. (orfermentation broth or harvest mash containing 45 the antibiotic) is active against nematodes. Accordingly, the present invention provides a method of controlling nematodes in warm-blooded animals and in soil containing the nematodes by introducing orally into the animals or applying to nematode-infested soil, a nernatocidally effective amount of antibiotic LL-C23024 a, or a pharmaceutically acceptable salt of the antibiotic, or a fermentation broth or harvest mash solids from which the nernatocidal antibiotic is obtained.
Antibiotic LL-C23024 ut is an organic carboxylic acid and thus is capable of forming salts with non-toxic pharmaceutically acceptable cations. Thus, salts formed by admixture of the antibiotic free acid with stoichiometric amounts of cations, suitably in a neutral solvent, may be formed with cations such as sodium, potassium, calcium, magnesium and ammonium, as well as organic amine cations such as tri(lower alkyl)amine (eg triethylamine, triethanola mine), procaine and the like. For the purposes of this invention, the 55 antibiotic free acid is equivalent to its pharmaceutically acceptable non- toxic salts.
Mixtures of the compound or salts may be used.
Claims (2)
1. A method of controlling nematodes in warm-blooded animals and in soil containing the nematodes, by introducing orally into the animals, or applying to nematode-infested soil, a nernatocidally effective amount of anti - biotic LL-C23024 a, or a pharmaceutically acceptable salt of the compound, or a fermentation broth or harvest mash solid from which the nernatocidal antibiotic is obtained.
GB 2 147 808 A 5
2. The use of antibiotic LL-C23024 a, or a pharmaceutically acceptable salt thereof, or a fermentation broth or harvest mash solid from which the controlling antibiotic is obtained, as a nematocidal agent for controlling nematodes in warm-blooded animals or in nematode-infested soil.
Printed in the UK for HMSO, D8818935, 3185, 7102. Published by The Patent Office, 25 Southampton Buildings, London, WC2A lAY, from which copies may be obtained.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/313,849 US4407946A (en) | 1981-10-22 | 1981-10-22 | Process for producing antibiotic X-14868A |
| US37278482A | 1982-04-28 | 1982-04-28 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8426115D0 GB8426115D0 (en) | 1984-11-21 |
| GB2147808A true GB2147808A (en) | 1985-05-22 |
| GB2147808B GB2147808B (en) | 1986-02-19 |
Family
ID=26979078
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08225339A Expired GB2108113B (en) | 1981-10-22 | 1982-09-06 | Antibacterial agents ll-c23024b and iota and microorganism actinomadura yumaense nrrl 12515 |
| GB08426115A Expired GB2147808B (en) | 1981-10-22 | 1984-10-16 | Controlling nematodes in soil or animals |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08225339A Expired GB2108113B (en) | 1981-10-22 | 1982-09-06 | Antibacterial agents ll-c23024b and iota and microorganism actinomadura yumaense nrrl 12515 |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPH0824593B2 (en) |
| AR (1) | AR229058A1 (en) |
| AU (1) | AU558914B2 (en) |
| CA (1) | CA1198386A (en) |
| CH (1) | CH661283A5 (en) |
| DE (1) | DE3238316A1 (en) |
| DK (1) | DK161332C (en) |
| ES (1) | ES516718A0 (en) |
| FI (1) | FI75187C (en) |
| FR (1) | FR2515207B1 (en) |
| GB (2) | GB2108113B (en) |
| HU (1) | HU190814B (en) |
| IE (1) | IE54813B1 (en) |
| IL (1) | IL66671A (en) |
| IT (1) | IT1197433B (en) |
| NL (1) | NL194396C (en) |
| SE (2) | SE8205992L (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR78648B (en) * | 1982-07-26 | 1984-09-27 | Bristol Myers Co | |
| DE102006028817A1 (en) * | 2006-06-21 | 2007-12-27 | Evonik Degussa Gmbh | Processing of Reaction Solutions from Whole Cell Biotransformations |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4278663A (en) * | 1980-01-30 | 1981-07-14 | Hoffmann-La Roche Inc. | Antibiotic X-14868A, B, C and D |
-
1982
- 1982-08-18 CA CA000409648A patent/CA1198386A/en not_active Expired
- 1982-08-29 IL IL66671A patent/IL66671A/en not_active IP Right Cessation
- 1982-09-06 GB GB08225339A patent/GB2108113B/en not_active Expired
- 1982-10-15 DE DE19823238316 patent/DE3238316A1/en active Granted
- 1982-10-18 DK DK462082A patent/DK161332C/en active
- 1982-10-20 AR AR291028A patent/AR229058A1/en active
- 1982-10-20 IT IT49317/82A patent/IT1197433B/en active
- 1982-10-21 IE IE2542/82A patent/IE54813B1/en not_active IP Right Cessation
- 1982-10-21 NL NL8204069A patent/NL194396C/en not_active IP Right Cessation
- 1982-10-21 SE SE8205992D patent/SE8205992L/en not_active Application Discontinuation
- 1982-10-21 HU HU823370A patent/HU190814B/en not_active IP Right Cessation
- 1982-10-21 CH CH6216/82A patent/CH661283A5/en not_active IP Right Cessation
- 1982-10-21 ES ES516718A patent/ES516718A0/en active Granted
- 1982-10-21 FI FI823603A patent/FI75187C/en not_active IP Right Cessation
- 1982-10-21 SE SE8205992A patent/SE456588C/en not_active IP Right Cessation
- 1982-10-21 AU AU89653/82A patent/AU558914B2/en not_active Expired
- 1982-10-22 FR FR8217727A patent/FR2515207B1/en not_active Expired
-
1984
- 1984-10-16 GB GB08426115A patent/GB2147808B/en not_active Expired
-
1992
- 1992-04-08 JP JP4114181A patent/JPH0824593B2/en not_active Expired - Lifetime
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 732E | Amendments to the register in respect of changes of name or changes affecting rights (sect. 32/1977) | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 20020905 |