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US4696922A
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5-azolylacetoxymilbemycins as ecto- and endoparasites
Assignee: Sankyo Co Ltd
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Filing: 1985-11-18
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Granted: 1987-09-29
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Expires: 2005-11-18
Abstract
Abstract The present invention relates to milbemycin derivatives of the formula I ##STR1## wherein X is hydrogen or β-halogen, R is methyl, ethyl, isopropyl or sec-butyl and Az is a 5 membered heterocyclic aromatic ring which contains 2-4 nitrogen atoms and is attached in the 1-position and which is unsubstituted or substituted by one or two C 1 -C 6 alkyl groups. These compounds, and the acid addition salts and metal complexes thereof, are effective pesticides for controlling endo-and ectoparasites, especially for controlling neamatodes which are parasites of animals. The may be obtained by appropriate esterification in 5-position of milbemycin derivatives. The selective β-halogenation of 14,15-epoxymilbemycin derivatives can be effected via the intermediate Δ 13 ,14 -15-hydroxymilbemycins with appropriate halogenating agents.
Inventors
- 👤 Elmar Sturm
- 👤 Peter Maienfisch
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 22:52
CPC Classifications
C; C07; C07H; C07H19/00; C07H19/01; A; A61; A61P; A61P33/00; A61P33/10
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
66 words
A milbemycin derivative of the formula I ##STR9## wherein X is hydrogen or β-halogen, R is methyl, ethyl, isopropyl or sec-butyl and Az is a 5 membered heterocyclic aromatic ring which contains 2-4 nitrogen atoms and is attached in the 1-position and which is unsubstituted or substituted by one or two C 1 -C 6 alkyl groups, or an acid addition salt or metal complex thereof.
Claim 2
Dependent Claim
66 words
A milbemycin derivative of the formula I ##STR9## wherein X is hydrogen or β-halogen, R is methyl, ethyl, isopropyl or sec-butyl and Az is a 5 membered heterocyclic aromatic ring which contains 2-4 nitrogen atoms and is attached in the 1-position and which is unsubstituted or substituted by one or two C 1 -C 6 alkyl groups, or an acid addition salt or metal complex thereof.
Claim 3
Dependent Claim
24 words
A compound of the formula I according to claim 1, wherein R is isopropyl and X and Az are as defined in claim 1.
Claim 4
Dependent Claim
33 words
A compound of the formula I according to claim 1, wherein Az is imidazole, pyrazole, 1,2,3-triazole, 1,2,4-triazole, tetrazole, 2-ethyl-4-methylimidazole, 2-isopropylimidazole, methylimidazole, 3,5-dimethyltriazole, ethyltriazole or 3,4-diethyltriazole, each of which is attached in the 1-position.
Claim 5
Dependent Claim
25 words
A compound of the formula I according to claim 3, wherein X is hydrogen or β-chlorine, R is ethyl or isopropyl, and Az is 1,2,4-triazol-1-yl.
Claim 6
Dependent Claim
9 words
5-O-(1,2,4-Triazol-1'-yl)acetyl-13-βchloromilbemycin D, or a salt or metal complex thereof.
Claim 7
Dependent Claim
9 words
5-O-(1,2,4-Triazol-1'-yl)acetyl-13-βchloromilbemycin D, or a salt or metal complex thereof.
Claim 8
Dependent Claim
25 words
A metal complex according to claim 5 with a metal selected from the group consisting of copper, zinc, manganese, chromium, iron, nickel, cobalt and molybdenum.
Claim 9
Dependent Claim
18 words
A pesticidal composition containing at least one compound according to claim 1 together with a suitable carrier therefor.
Claim 10
Dependent Claim
15 words
A pesticidal composition according to claim 7, which contains a compound according to claim 2.
Claim 11
Dependent Claim
15 words
A pesticidal composition according to claim 7, which contains a compound according to claim 3.
Claim 12
Dependent Claim
15 words
A pesticidal composition according to claim 7, which contains a compound according to claim 4.
Claim 13
Dependent Claim
15 words
A pesticidal composition according to claim 7, which contains a compound according to claim 5.
Claim 14
Dependent Claim
15 words
A pesticidal composition according to claim 7, which contains a compound according to claim 6.
Claim 15
Dependent Claim
31 words
A method of controlling insects and pests of the order Acarina at a locus, which comprises applying to said locus a pesticidally effective amount of a compound according to claim 1.
Claim 16
Dependent Claim
29 words
A method according to claim 13 of controlling nematodes at a locus, which comprises applying to said locus a nematicidally effective amount of a compound according to claim 1.
Claim 17
Dependent Claim
31 words
A method of controlling ecto- and endoparasites on or in warm-blooded animals, which comprises applying or administering to said animals a pesticidally effective amount of a compound according to claim 1.
Claim 18
Dependent Claim
31 words
A method of controlling pests which are parasites of animals or plants, which comprises applying to said animals or plants a pesticidally effective amount of a compound according to claim 1.
References Cited (Backward Citations)
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1990-09-28 | 1991-03-30 | 1991-09-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-09-28 | 1995-03-30 | 1995-09-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-09-28 | 1999-03-30 | 1999-09-29 | $7700.00 | Window Closed / Lapsed |