US4414210A
Expired / Lapsed
US
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2-Hydroxyarylethyltriazole fungicides
Assignee: Rohm and Haas Asia Inc
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Filing: 1981-05-19
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Granted: 1983-11-08
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Expires: 2001-05-19
Abstract
Abstract This invention relates to 2-hydroxyarylethyl-1,2,4-triazoles, their acid addition salts and metal salt complexes. This invention also relates to the method of preparation and use of these compounds. These compounds and salts thereof are highly active broad-spectrum systemic fungicides effective in controlling phytopathogenic fungi such as barley net blotch (Helminthosporium teres), grey mold (Botrytis fabae), bean powdery mildew (Erysiphe polygoni), grape downy mildew (Plasmopora viticola), rice blast (Piricularia oryzae), tomato late blight (Phytophthora infestans) and wheat stem rust (Puccinia graminis f. sp. tritici race 158-2).
Inventors
- 👤 George A. Miller
- 👤 Hak-Foon Chan
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 14:58
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/02; C07D231/10; C07D231/12; A; A01; A01N; A01N43/00; A01N43/64; A01N43/647; A01N43/653; C07D233/00; C07D233/54; C07D233/56; C07D249/00; C07D249/02; C07D249/08
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
198 words
A compound of the formula ##STR14## wherein Z is an unsubstituted phenyl or naphthyl group or a phenyl or naphthyl group substituted with up to three substituents selected from the group consisting of halogen, nitro, trihalomethyl, cyano, (C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio, (C 1 -C 4 )alkylsulfinyl, (C 1 -C 4 )alkylsulfonyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl and phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl substituted with up to two substituents selected from the group consisting of halogen, nitro, trifluoromethyl, cyano, methyl, methoxy, methylthio, methylsulfinyl and methylsulfonyl; R 1 is cyano (C 3 -C 12 )alkyl, (C 3 -C 8 )cycloalkyl, (C 2 -C 8 )alkenyl, (C 5 -C 8 )cycloalkenyl, (C 2 -C 8 )alkynyl, unsubstituted phenyl or phenyl substituted with up to two substituents selected from the group consisting of halogen, nitro, trihalomethyl, cyano, methyl, methoxy, methylsulfinyl and methylsulfonyl; or unsubstituted benzyl or phenethyl, or benzyl or phenethyl substituted with up to two substituents selected from the group consisting of halogen, nitro, trihalomethyl, cyano, methyl, methoxy, methylthio, methylsulfinyl, and methylsulfonyl; and W is a 1 or 4-(1,2,4-triazole); and the agronomically acceptable acid addition salts and metal said complexes thereof.
Claim 2
Dependent Claim
198 words
A compound of the formula ##STR14## wherein Z is an unsubstituted phenyl or naphthyl group or a phenyl or naphthyl group substituted with up to three substituents selected from the group consisting of halogen, nitro, trihalomethyl, cyano, (C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio, (C 1 -C 4 )alkylsulfinyl, (C 1 -C 4 )alkylsulfonyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl and phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl substituted with up to two substituents selected from the group consisting of halogen, nitro, trifluoromethyl, cyano, methyl, methoxy, methylthio, methylsulfinyl and methylsulfonyl; R 1 is cyano (C 3 -C 12 )alkyl, (C 3 -C 8 )cycloalkyl, (C 2 -C 8 )alkenyl, (C 5 -C 8 )cycloalkenyl, (C 2 -C 8 )alkynyl, unsubstituted phenyl or phenyl substituted with up to two substituents selected from the group consisting of halogen, nitro, trihalomethyl, cyano, methyl, methoxy, methylsulfinyl and methylsulfonyl; or unsubstituted benzyl or phenethyl, or benzyl or phenethyl substituted with up to two substituents selected from the group consisting of halogen, nitro, trihalomethyl, cyano, methyl, methoxy, methylthio, methylsulfinyl, and methylsulfonyl; and W is a 1 or 4-(1,2,4-triazole); and the agronomically acceptable acid addition salts and metal said complexes thereof.
Claim 3
Dependent Claim
94 words
The compound of claim 1 wherein R 1 is (C 3 -C 8 )-alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 4 )alkenyl, (C 5 -C 6 )cycloalkenyl, (C 2 -C 4 )alkynyl, unsubstituted phenyl or phenyl substituted with up to two substituents selected from the group consisting of halogen, nitro, trihalomethyl, cyano, methyl, methoxy, methylsulfinyl and methylsulfonyl; or unsubstituted benzyl or phenethyl, or benzyl or phenethyl substituted with up to two substituents selected from the group consisting of halogen, nitro, trihalomethyl, cyano, methyl, methoxy, methylthio, methylsulfinyl, and methylsulfonyl; and W is 1-(1,2,4-triazole).
Claim 4
Dependent Claim
52 words
A compound of the formula ##STR15## wherein Z is unsubstituted phenyl or phenyl substituted with up to three substituents selected from the group consisting of halogen, (C 1 -C 4 )alkyl and (C 1 -C 4 )alkoxy; R 1 is (C 4 -C 8 )alkyl, phenyl or benzyl; and W is 1-(1,2,4-triazole).
Claim 5
Dependent Claim
52 words
A compound of the formula ##STR15## wherein Z is unsubstituted phenyl or phenyl substituted with up to three substituents selected from the group consisting of halogen, (C 1 -C 4 )alkyl and (C 1 -C 4 )alkoxy; R 1 is (C 4 -C 8 )alkyl, phenyl or benzyl; and W is 1-(1,2,4-triazole).
Claim 6
Dependent Claim
37 words
The compound of claim 3 wherein Z is unsubstituted phenyl or phenyl substituted with up to two substituents selected from the group consisting of chloro, methyl and methoxy; and R 1 is n-butyl, n-octyl, benzyl or phenyl.
Claim 7
Dependent Claim
21 words
The compound of claim 4 wherein Z is phenyl, 4-methylphenyl, 2,4-dichlorophenyl or 4-methoxyphenyl; R 1 is n-butyl, n-octyl, phenyl or benzyl.
Claim 8
Dependent Claim
9 words
The compound of claim 5 having the structure ##STR16##
Claim 9
Dependent Claim
21 words
The compound of claim 5 having the structure ##STR17## and the agronomically acceptable acid addition salts and metal salt complexes thereof.
Claim 10
Dependent Claim
21 words
The compound of claim 5 having the structure ##STR18## and the agronomically acceptable acid addition salts and metal salt complexes thereof.
Claim 11
Dependent Claim
21 words
The compound of claim 5 having the structure ##STR19## and the agronomically acceptable acid addition salts and metal salt complexes thereof.
Claim 12
Dependent Claim
21 words
The compound of claim 1 having the structure ##STR20## and the agronomically acceptable acid addition salt and metal salt complexes thereof.
Claim 13
Dependent Claim
25 words
A fungicidal composition which comprises, an agronomically acceptable carrier and as the active ingredient, a fungicidally effective amount of a compound according to claim 2.
Claim 14
Dependent Claim
30 words
A method for controlling phytopathogenic fungi which comprises, applying to the plant, the plant seed or the plant habitat a fungicidally effective amount of a compound according to claim 2.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-11-07 | 1987-05-09 | 1987-11-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-11-07 | 1991-05-09 | 1991-11-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-11-07 | 1995-05-09 | 1995-11-08 | $7700.00 | Window Closed / Lapsed |