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US4366165A
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1 and 4-Arylcyanoalkyl-1,2,4-triazoles and fungicidal use
Assignee: Rohm and Haas Co
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Filing: 1981-02-11
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Granted: 1982-12-28
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Expires: 2001-02-11
Abstract
Abstract This invention relates to 1 and 4-arylcyanoalkyl-1,2,4-triazoles, their enantiomorphs, and acid addition salts and metal salt complexes. This invention also relates to the method of preparation and use of these compounds. These compounds enantiomorphs, salts and complexes are highly active broad-spectrum systemic fungicides effective in controlling phytopathogenic fungi such as barley net blotch (Helminthosporium teres), grey mold (Botrytis cinerea), 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 15B-2).
Inventors
- 👤 George A. Miller
- 👤 Hak-Foon Chan
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 03:59
CPC Classifications
C; C07; C07D; C07D249/00; C07D249/02; C07D249/08; A; A01; A01N; A01N43/00; A01N43/64; A01N43/647; A01N43/653
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
125 words
A compound of the formula ##STR9## wherein Z is unsubstituted phenyl, or phenyl 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 and (C 1 -C 4 )alkylsulfonyl, R is selected from the group consisting of (C 1 -C 12 )alkyl, (C 5 -C 7 )cycloalkyl, (C 2 -C 4 )alkenyl, (C 5 -C 6 )cycloalkenyl, (C 2 -C 4 )alkynyl, unsubstituted phenyl, benzyl or phenethyl, or phenyl, benzyl or phenethyl substituted with up to two halogen atoms; Q is an unsubstituted 1- or 4-(1,2,4-triazole) and the agronomically acceptable enantiomorphs, acid addition salts and metal salt complexes thereof.
Claim 2
Dependent Claim
125 words
A compound of the formula ##STR9## wherein Z is unsubstituted phenyl, or phenyl 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 and (C 1 -C 4 )alkylsulfonyl, R is selected from the group consisting of (C 1 -C 12 )alkyl, (C 5 -C 7 )cycloalkyl, (C 2 -C 4 )alkenyl, (C 5 -C 6 )cycloalkenyl, (C 2 -C 4 )alkynyl, unsubstituted phenyl, benzyl or phenethyl, or phenyl, benzyl or phenethyl substituted with up to two halogen atoms; Q is an unsubstituted 1- or 4-(1,2,4-triazole) and the agronomically acceptable enantiomorphs, acid addition salts and metal salt complexes thereof.
Claim 3
Dependent Claim
55 words
A compound according to claim 1 wherein Z is phenyl, or phenyl substituted with up to two substituents selected from the group consisting of chlorine, bromine, methyl, methoxy, nitro and methylthio; R is (C 1 to C 12 ) alkyl, cyclohexyl, allyl, cyclohexenyl, propargyl, phenyl, benzyl or phenethyl, or monochloro substituted phenyl, benzyl or phenethyl.
Claim 4
Dependent Claim
39 words
A compound according to claim 2 wherein Z is phenyl, or phenyl substituted with up to two substituents selected from the group consisting of chlorine and methyl and R is (C 1 to C 8 ) alkyl or allyl.
Claim 5
Dependent Claim
39 words
A compound according to claim 3 wherein Z is 2,4-dichlorophenyl, R is CH 3 , n--C 4 H 9 , n--C 8 H 17 or allyl; Q is 1-(1,2,4-triazolyl); and the agronomically acceptable enantimorphs, and acid addition salts thereof.
Claim 6
Dependent Claim
28 words
A compound according to claim 3 wherein Z is phenyl; R is n--C 4 H 9 ; Q is 1-(1,2,4,-triazolyl); and the agronomically acceptable acid addition salts thereof.
Claim 7
Dependent Claim
29 words
A fungicidal composition for controlling phytopathogenic fungi which comprises, an agronomically acceptable carrier and as the active ingredient, a fungicidally effective amount of a compound according to claim 2.
Claim 8
Dependent Claim
29 words
A fungicidal composition for controlling phytopathogenic fungi which comprises, an agronomically acceptable carrier and as the active ingredient, a fungicidally effective amount of a compound according to claim 5.
Claim 9
Dependent Claim
32 words
A method for controlling phytopathogenic fungi which consists of applying to a plant, to plant seed or to the plant habitat, a fungicidally effective amount of a compound according to claim 2.
Claim 10
Dependent Claim
32 words
A method for controlling phytopathogenic fungi which consists of applying to a plant, to plant seed or to the plant habitat, a fungicidally effective amount of a compound according to claim 5.
Claim 11
Dependent Claim
43 words
A compound according to claim 1 wherein Z is phenyl, or phenyl substituted with up to two substituents selected from the group consisting of chlorine, fluorine and methoxy, R is (C 1 to C 8 ) alkyl or allyl and Q is 1-(1,2,4-triazolyl).
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) | 1985-12-27 | 1986-06-28 | 1986-12-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-12-27 | 1990-06-28 | 1990-12-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-12-27 | 1994-06-28 | 1994-12-28 | $7700.00 | Window Closed / Lapsed |