US4918097A
Expired / Lapsed
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Insecticides and parasiticides
Assignee: Sankyo Co Ltd
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Filing: 1989-03-01
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Granted: 1990-04-17
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Expires: 2009-03-01
Abstract
Abstract The present invention relates to novel derivatives of formula I that can be derived from milbemycins, to their preparation and their use for controlling pests, and also to pesticides that contain at least one of these compounds as active ingredient. The novel compounds have the general formula I ##STR1## in which X is one of the groups --CH(OR 1 )--, --C(O)-- or --C(=N--OR)--; R 1 is hydrogen or an OH-protecting group; R is hydrogen, an OH-protecting group, or an alkyl or cycloalkyl group; R 2 is methyl, ethyl, isopropyl or sec.-butyl; and Ph is a phenyl ring that is substituted by R a , R b , R c and R d , wherein each of R a , R b , R c and R d , independently of the others, is hydrogen, C 1 -C 10 alkyl, C 2 -C 10 alkoxyalkyl, C 2 -C 10 alkenyl, C 1 -C 10 alkoxy, C 2 -C 10 alkoxyalkoxy, or a phenyl or phenoxy radical that is unsubstituted or is substituted by at least one substituent from the group C 1 -C 3 alkyl and C 1 -C 3 alkoxy.
Inventors
- 👤 Anthony C. O'Sullivan
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 10:37
CPC Classifications
C; C07; C07D; C07D493/00; C07D493/22; C07H; C07H19/00; C07H19/01; A; A01; A01N; A01N43/00; A01N43/90; A61; A61K; A61K31/00; A61K31/33; A61K31/335; A61K31/365; A61P; A61P33/00; A61P33/10; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
146 words
Compounds of formula I ##STR11## in which X is one of the groups --CH(OR 1 )--, --C(O)-- or --C(═N--OR)--; R 1 is hydrogen or an OH-protecting group; R is hydrogen, an OH-protecting group, or an alkyl or cycloalkyl group; R 2 is methyl, ethyl, isopropyl or sec.-butyl; and Ph is a phenyl ring that is substituted by R a , R b , R c and R d , wherein each of R a , R b , R c and R d , independently of the others, is hydrogen, C 1 -C 10 alkyl, C 2 -C 10 alkoxyalkyl, C 2 -C 10 alkenyl, C 1 -C 10 alkoxy, C 2 -C 10 alkoxyalkoxy, or a phenyl or phenoxy radical that is unsubstituted or is substituted by at least one substituent from the group C 1 -C 3 alkyl and C 1 -C 3 alkoxy.
Claim 2
Dependent Claim
146 words
Compounds of formula I ##STR11## in which X is one of the groups --CH(OR 1 )--, --C(O)-- or --C(═N--OR)--; R 1 is hydrogen or an OH-protecting group; R is hydrogen, an OH-protecting group, or an alkyl or cycloalkyl group; R 2 is methyl, ethyl, isopropyl or sec.-butyl; and Ph is a phenyl ring that is substituted by R a , R b , R c and R d , wherein each of R a , R b , R c and R d , independently of the others, is hydrogen, C 1 -C 10 alkyl, C 2 -C 10 alkoxyalkyl, C 2 -C 10 alkenyl, C 1 -C 10 alkoxy, C 2 -C 10 alkoxyalkoxy, or a phenyl or phenoxy radical that is unsubstituted or is substituted by at least one substituent from the group C 1 -C 3 alkyl and C 1 -C 3 alkoxy.
Claim 3
Dependent Claim
130 words
Compounds of formula I according to claim 1, wherein X is --CH(OR 1 )-- and R 1 is hydrogen or a protecting group, R 2 is methyl, ethyl, isopropyl or sec.-butyl; and Ph is a phenyl ring that is substituted by R a , R b , R c and R d , wherein each of R a , R b , R c and R d , independently of the others, is hydrogen, C 1 -C 10 alkyl, C 2 -C 10 alkoxyalkyl, C 2 -C 10 alkenyl, C 1 -C 10 alkoxy, C 2 -C 10 alkoxyalkoxy, or a phenyl or phenoxy radical that is unsubstituted or is substituted by at least one substituent from the group C 1 -C 3 alkyl and C 1 -C 3 alkoxy.
Claim 4
Dependent Claim
126 words
Compounds of formula I according to claim 1, wherein X is --CH(OR 1 )-- and R 1 is hydrogen, R 2 is methyl, ethyl, isopropyl or sec.-butyl; and Ph is a phenyl ring that is substituted by R a , R b , R c and R d , wherein each of R a , R b , R c and R d , independently of the others, is hydrogen, C 1 -C 10 alkyl, C 2 -C 10 alkoxyalkyl, C 2 -C 10 alkenyl, C 1 -C 10 alkoxy, C 2 -C 10 alkoxyalkoxy, or a phenyl or phenoxy radical that is unsubstituted or is substituted by at least one substituent from the group C 1 -C 3 alkyl and C 1 -C 3 alkoxy.
Claim 5
Dependent Claim
124 words
Compounds of formula I according to claim 1, wherein X is --CH(OR 1 )-- and R 1 is hydrogen, R 2 is methyl or ethyl; and Ph is a phenyl ring that is substituted by R a , R b , R c and R d , wherein each of R a , R b , R c and R d , independently of the others, is hydrogen, C 1 -C 10 alkyl C 2 -C 10 alkoxyalkyl, C 2 -C 10 alkenyl, C 1 -C 10 alkoxy, C 2 -C 10 alkoxyalkoxy, or a phenyl or phenoxy radical that is unsubstituted or is substituted by at least one substituent from the group C 1 -C 3 alkyl and C 1 -C 3 alkoxy.
Claim 6
Dependent Claim
94 words
Compounds of formula I according to claim 1, wherein X is --CH(OR 1 )-- and R 1 is hydrogen, R 2 is methyl or ethyl; and Ph is a phenyl ring that is substituted by R a , R b , R c and R d , wherein each of R a , R b , R c and R d , independently of the others, is hydrogen, C 1 -C 10 alkyl, C 2 -C 10 alkoxyalkyl, C 2 -C 10 alkenyl, C 1 -C 10 alkoxy or C 2 -C 10 alkoxyalkoxy.
Claim 7
Dependent Claim
99 words
Compounds of formula I according to claim 1, wherein X is --CH(OR 1 )-- and R 1 is hydrogen, R 2 is methyl or ethyl; and Ph is a phenyl ring that is substituted by R a , R b , R c and R d , wherein each of R a , R b , R c and R d , independently of the others, is hydrogen, or a phenyl or phenoxy radical that is unsubstituted or is substituted by at least one substituent from the group C 1 -C 3 alkyl and C 1 -C 3 alkoxy.
Claim 8
Dependent Claim
107 words
Compounds of formula I according to claim 1, wherein X is --CH(OR 1 )-- and R 1 is hydrogen, R 2 is methyl or ethyl; and Ph is a phenyl ring that is substituted by R a , R b , R c and R d , wherein each of R a , R b , R c and R d , independently of the others, is hydrogen, C 1 -C 3 alkyl or C 1 -C 3 alkoxy, with the proviso that not more than two of the substituents R a , R b , R c and R d have a meaning other than hydrogen.
Claim 9
Dependent Claim
99 words
Compounds of formula I according to claim 1, wherein X is --CH(OR 1 )-- and R 1 is hydrogen, R 2 is methyl or ethyl; and Ph is a phenyl ring that is substituted by R a , R b , R c and R d , wherein each of R a , R b , R c and R d , independently of the others, is hydrogen, phenyl or phenoxy, with the proviso that not more than two of the substituents R a , R b , R c and R d have a meaning other than hydrogen.
Claim 10
Dependent Claim
50 words
Compounds of formula I according to claim 1, wherein X is --CH(OR 1 )-- and R 1 is hydrogen, R 2 is methyl or ethyl; and Ph is phenyl that is unsubstituted or monosubstituted by methyl, methoxy, phenyl or phenoxy, or disubstituted by methyl or methoxy, or trisubstituted by methyl.
Claim 11
Dependent Claim
48 words
Compounds of formula I according to claim 1, wherein X is --CH(OR 1 )-- and R 1 is hydrogen, R 2 is ethyl; and Ph is phenyl that is unsubstituted or monosubstituted by methyl, methoxy, phenyl or phenoxy, or disubstituted by methyl or methoxy, or trisubstituted by methyl.
Claim 12
Dependent Claim
44 words
Compounds of formula I according to claim 1, wherein X is --CH(OR 1 )-- and R 1 is hydrogen, R 2 methyl or, especially, ethyl; and Ph is phenyl that is unsubstituted or monosubstituted by methyl, methoxy, phenyl or phenoxy, or disubstituted by methoxy.
Claim 13
Dependent Claim
41 words
A compound of formula I selected from the group: 13β-phenyl-milbemycin A 4 , 13β-(2-methoxyphenyl)-milbemycin A 4 , 13β-(3-methoxyphenyl)-milbemycin A 4 , 13β-(4-methoxyphenyl)-milbemycin A 4 , 13β-(2-methylphenyl)-milbemycin A 4 , 13β-(4-biphenylyl)-milbemycin A 4 , 13β-(4-phenoxyphenyl)-milbemycin A 4 and 13β-(3,4-dimethoxyphenyl)-milbemycin A 4 .
Claim 14
Dependent Claim
41 words
A compound of formula I selected from the group: 13β-phenyl-milbemycin A 4 , 13β-(2-methoxyphenyl)-milbemycin A 4 , 13β-(3-methoxyphenyl)-milbemycin A 4 , 13β-(4-methoxyphenyl)-milbemycin A 4 , 13β-(2-methylphenyl)-milbemycin A 4 , 13β-(4-biphenylyl)-milbemycin A 4 , 13β-(4-phenoxyphenyl)-milbemycin A 4 and 13β-(3,4-dimethoxyphenyl)-milbemycin A 4 .
Claim 15
Dependent Claim
21 words
A compound of formula I selected from the group: 13β-phenyl-milbemycin A 3 , 13β-(2-methylphenyl)-milbemycin A 4 and 13β-(4-methylphenyl)-milbemycin A 4 .
Claim 16
Dependent Claim
21 words
A compound of formula I selected from the group: 13β-phenyl-milbemycin A 3 , 13β-(2-methylphenyl)-milbemycin A 4 and 13β-(4-methylphenyl)-milbemycin A 4 .
Claim 17
Dependent Claim
30 words
Compositions for controlling pests, which contain at least one compound of formula I according to claim 1 as active ingredient, together with carriers, distributing agents or carriers and distributing agents.
Claim 18
Dependent Claim
36 words
A method of controlling pests, which comprises applying or administering a pesticidally effective amount of a compound of formula I according to claim 1 to the host animals, host plants or other loci of the pests.
Claim 19
Dependent Claim
18 words
A method according to claim 15, wherein the pests to be controlled are endo- or ecto-parasites of animals.
Claim 20
Dependent Claim
15 words
A method according to claim 15, wherein the pests to be controlled are plant-destructive parasites.
Claim 21
Dependent Claim
12 words
A method according to claim 15, wherein the pests are parasitic nematodes.
References Cited (Backward Citations)
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| 3.5 Years (Year 4) | 1993-04-16 | 1993-10-16 | 1994-04-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-04-16 | 1997-10-16 | 1998-04-17 | $3760.00 | Window Closed / Lapsed |
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