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US4571397A
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Pyridazinone derivatives, preparation thereof, and agricultural and horticultural fungicidal, insecticidal, acaricidal, nematicidal compositions containing said derivatives
Assignee: Nissan Chemical Corp
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Filing: 1983-02-17
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Granted: 1986-02-18
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Expires: 2003-02-17
Abstract
Abstract Novel 5-substituted -3(2H)-pyridazinone derivatives and preparation thereof are provided. The derivatives have the formula: ##STR1## wherein, R denotes an alkyl, R 1 and R 2 denote each independently hydrogen or a lower alkyl, X denotes hydrogen, a lower alkyl, a halogen, a lower alkoxy, a lower haloalkyl, a lower haloalkoxy, a cycloalkyl, trimethylsilyl (-Si(CH 3 ) 3 ), ##STR2## (wherein Y denotes hydrogen, a halogen, a lower alkyl, a lower alkoxy, a lower haloalkyl, a lower haloalkoxy or a cycloalkyl, and m is an integer of 1 to 5), n is an integer of 1 to 5, and Z denotes a halogen; said X being the same or different when n is 2 or more, and the alkyls and the alkyl moieties contained in the groups being straight or branched.
Inventors
- 👤 Masakazu Taniguchi
- 👤 Masatoshi Baba
- 👤 Yoshinori Ochiai
- 👤 Masayoshi Hirose
- 👤 Kiminori Hirata
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 00:10
CPC Classifications
A; A01; A01N; A01N55/00; A01N43/00; A01N43/48; A01N43/58; C; C07; C07D; C07D237/00; C07D237/02; C07D237/06; C07D237/10; C07D237/14; C07D237/16; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/0803; C07F7/081; C07F7/0812
Claims Analysis
Total Claims: 38
Claim 1
Independent Claim
189 words
A compound of the formula I: ##STR41## wherein, R denotes an C 1 to C 6 alkyl, R 1 and R 2 denote each independently hydrogen or a C 1 to C 6 alkyl, X denotes hydrogen, a C 1 to C 6 alkyl, a halogen, a C 1 to C 6 alkoxy, a C 1 to C 6 haloalkyl, a C 1 to C 6 haloalkoxy, C 5 to C 6 cycloalkyl, trimethylsilyl (--Si(CH 3 ) 3 ), ##STR42## (wherein Y denotes hydrogen, a halogen, a C 1 to C 6 alkyl, a C 1 to C 6 alkoxy, a C 1 to C 6 haloalkyl, a C 1 to C 6 haloalkoxy or a cycloalkyl, and m is an integer of 1 to 5), n is an integer of 1 to 5, and Z denotes a halogen; said X being the same or different when n is 2 or more, the alkyls and the alkyl moieties contained in the groups being straight or branched, and the halogen itself or the halogen contained in the groups being selected from fluorine, chlorine, bromine or iodine or a mixture thereof.
Claim 2
Dependent Claim
189 words
A compound of the formula I: ##STR41## wherein, R denotes an C 1 to C 6 alkyl, R 1 and R 2 denote each independently hydrogen or a C 1 to C 6 alkyl, X denotes hydrogen, a C 1 to C 6 alkyl, a halogen, a C 1 to C 6 alkoxy, a C 1 to C 6 haloalkyl, a C 1 to C 6 haloalkoxy, C 5 to C 6 cycloalkyl, trimethylsilyl (--Si(CH 3 ) 3 ), ##STR42## (wherein Y denotes hydrogen, a halogen, a C 1 to C 6 alkyl, a C 1 to C 6 alkoxy, a C 1 to C 6 haloalkyl, a C 1 to C 6 haloalkoxy or a cycloalkyl, and m is an integer of 1 to 5), n is an integer of 1 to 5, and Z denotes a halogen; said X being the same or different when n is 2 or more, the alkyls and the alkyl moieties contained in the groups being straight or branched, and the halogen itself or the halogen contained in the groups being selected from fluorine, chlorine, bromine or iodine or a mixture thereof.
Claim 3
Dependent Claim
131 words
A compound according to claim 1, in which the compound is represented by the formula IA: ##STR43## wherein, R 3 denotes a C 1 to C 6 alkyl, R 4 denotes a C 1 to C 6 alkyl; R 5 denotes hydrogen or a C 1 to C 6 alkyl; X 1 denotes hydrogen, a C 1 to C 6 alkyl, a C 1 to C 6 alkoxy, a C 1 to C 6 haloalkyl, a C 1 to C 6 haloalkoxy, a halogen or a C 5 to C 6 cycloalkyl, and n 1 is an integer of 1 to 5; said X 1 being the same or different when n is 2 to 5, and the alkyls and the alkyl moieties contained in the groups being straight or branched.
Claim 4
Dependent Claim
97 words
A compound according to claim 1, in which the compound is represented by the formula IB: ##STR44## wherein, R 6 denotes an alkyl having 1 to 6 carbon atoms; X 2 denotes hydrogen, a halogen, a C 1 to C 6 alkyl, a C 1 to C 6 alkoxy or a C 1 to C 6 haloalkyoxy; and n 2 is an integer of 1 to 3; said X 2 being the same or different when n 2 is 2 or 3 and the alkyls and the alkyl moieties contained in the groups being straight or branched.
Claim 5
Dependent Claim
26 words
A compound according to claim 1, in which the compound is represented by the formula IC: ##STR45## wherein, R 7 denotes a straight or branched alkyl.
Claim 6
Dependent Claim
183 words
A compound according to claim 1, in which the compound is represented by the formula ID: ##STR46## wherein, R 8 denotes a C 1 to C 6 alkyl; R 9 and R 10 denote each independently hydrogen or a C 1 to C 6 alkyl; X 4 denotes hydrogen, a C 1 to C 6 alkyl, a halogen, a C 1 to C 6 cycloalkyl, trimethylsilyl, ##STR47## (wherein Y 4 denotes hydrogen, a halogen, a C 1 to C 6 alkyl, a C 1 to C 6 alkoxy, a C 1 to C 6 haloalkyl, a C 1 to C 6 haloalkoxy or a C 5 to C 6 cycloalkyl and m 4 is an integer of 1 to 5, said Y 4 being the same or different when m 4 is an integer of 2 to 5); n 4 is an integer of 1 to 3; and Z 4 is a halogen; said X 4 being the same or different when n 4 is 2 or 3 and the alkyls and the alkyl moieties contained in the groups being straight or branched.
Claim 7
Dependent Claim
54 words
A compound of the formula I: ##STR48## wherein R is t-C 4 H 9 , Z is Cl, R 1 is H, R 2 is H or CH 3 , X is, at 4-position, CH 3 , t-C 4 H 9 , F, ##STR49## or --Si(CH 3 ) 3 , and n is 1.
Claim 8
Dependent Claim
54 words
A compound of the formula I: ##STR48## wherein R is t-C 4 H 9 , Z is Cl, R 1 is H, R 2 is H or CH 3 , X is, at 4-position, CH 3 , t-C 4 H 9 , F, ##STR49## or --Si(CH 3 ) 3 , and n is 1.
Claim 9
Dependent Claim
216 words
A process for preparing a compound of the formula I: ##STR50## wherein, R denotes a C 1 to C 6 alkyl, R 1 and R 2 denote each independently hydrogen or a C 1 to C 6 alkyl, X denotes hydrogen, a C 1 to C 6 alkyl, a halogen, a C 1 to C 6 alkoxy, a C 1 to C 6 haloalkyl, a C 1 to C 6 haloalkoxy, a cycloalkyl, trimethylsilyl (--Si(CH 3 ) 3 ), ##STR51## (wherein Y denotes hydrogen, a halogen, a C 1 to C 6 alkyl, a C 1 to C 6 alkoxy, a C 1 to C 6 haloalkyl, a C 1 to C 6 haloalkoxy or a cycloalkyl, and m is an integer of 1 to 5), n is an integer of 1 to 5, and Z denotes a halogen; said X being the same or different when n is 2 or more, and the alkyls and the alkyl moieties contained in the groups being straight or branched, by reacting a compound of the formula II: ##STR52## (wherein R and Z are as defined in the above) with a compound of the formula III: ##STR53## (wherein R 1 , R 2 , X and n are as defined in the above and Hal denotes a halogen atom).
Claim 10
Dependent Claim
216 words
A process for preparing a compound of the formula I: ##STR50## wherein, R denotes a C 1 to C 6 alkyl, R 1 and R 2 denote each independently hydrogen or a C 1 to C 6 alkyl, X denotes hydrogen, a C 1 to C 6 alkyl, a halogen, a C 1 to C 6 alkoxy, a C 1 to C 6 haloalkyl, a C 1 to C 6 haloalkoxy, a cycloalkyl, trimethylsilyl (--Si(CH 3 ) 3 ), ##STR51## (wherein Y denotes hydrogen, a halogen, a C 1 to C 6 alkyl, a C 1 to C 6 alkoxy, a C 1 to C 6 haloalkyl, a C 1 to C 6 haloalkoxy or a cycloalkyl, and m is an integer of 1 to 5), n is an integer of 1 to 5, and Z denotes a halogen; said X being the same or different when n is 2 or more, and the alkyls and the alkyl moieties contained in the groups being straight or branched, by reacting a compound of the formula II: ##STR52## (wherein R and Z are as defined in the above) with a compound of the formula III: ##STR53## (wherein R 1 , R 2 , X and n are as defined in the above and Hal denotes a halogen atom).
Claim 11
Dependent Claim
24 words
A process according to claim 7, wherein the reaction is carried out in an inert solvent in the presence of a hydrogen halide-absorbing agent.
Claim 12
Dependent Claim
43 words
A process according to claim 7, wherein the reaction is carried out in the presence of a hydrogen-absorbing agent selected from sodium carbonate, potassium carbonate and triethylamine at a temperature of from room temperature up to the boiling point of the solvent employed.
Claim 13
Dependent Claim
195 words
A agricultural and horticultural fungicidal, insecticidal, acaricidal, nematocidal composition containing as an active ingredient an effective amount of a compound of the formula I: ##STR54## wherein, R denotes a C 1 to C 6 alkyl, R 1 and R 2 denote each independently hydrogen or a C 1 to C 6 alkyl, X denotes hydrogen, a C 1 to C 6 alkyl, a halogen, a C 1 to C 6 alkoxy, a C 1 to C 6 haloalkyl, a C 1 to C 6 haloalkoxy, a C 1 to C 6 cycloalkyl, trimethylsilyl (--Si(CH 3 ) 3 ), ##STR55## (wherein Y denotes hydrogen, a halogen, a C 1 to C 6 alkyl, a C 1 to C 6 alkoxy, a C 1 to C 6 haloalkyl, a C 1 to C 6 haloalkoxy or a C 5 to C 6 cycloalkyl, and m is an integer of 1 to 5), n is an integer of 1 to 5, and Z denotes a halogen; said X being the same or different when n is 2 or more, and the alkyls and the alkyl moieties contained in the groups being straight or branched, and a carrier therefor.
Claim 14
Dependent Claim
195 words
A agricultural and horticultural fungicidal, insecticidal, acaricidal, nematocidal composition containing as an active ingredient an effective amount of a compound of the formula I: ##STR54## wherein, R denotes a C 1 to C 6 alkyl, R 1 and R 2 denote each independently hydrogen or a C 1 to C 6 alkyl, X denotes hydrogen, a C 1 to C 6 alkyl, a halogen, a C 1 to C 6 alkoxy, a C 1 to C 6 haloalkyl, a C 1 to C 6 haloalkoxy, a C 1 to C 6 cycloalkyl, trimethylsilyl (--Si(CH 3 ) 3 ), ##STR55## (wherein Y denotes hydrogen, a halogen, a C 1 to C 6 alkyl, a C 1 to C 6 alkoxy, a C 1 to C 6 haloalkyl, a C 1 to C 6 haloalkoxy or a C 5 to C 6 cycloalkyl, and m is an integer of 1 to 5), n is an integer of 1 to 5, and Z denotes a halogen; said X being the same or different when n is 2 or more, and the alkyls and the alkyl moieties contained in the groups being straight or branched, and a carrier therefor.
Claim 15
Dependent Claim
53 words
A composition according to claim 10, wherein R is t-C 4 H 9 , Z is C, R 1 is H, R 2 is H or CH 3 , X is, at 4-position, CH 3 , t-C 4 H 9 , F, ##STR56## or --Si(CH 3 ) 3 , and n is 1.
Claim 16
Independent Claim
191 words
A method for fungicidal, insecticidal, acaricidal, nematocidal treatment in the agricultural and horticultural field with an effective amount of a compound of the formula (I): ##STR57## wherein, R denotes a C 1 to C 6 alkyl, R 1 and R 2 denote each independently hydrogen or a C 1 to C 6 alkyl, X denotes hydrogen, a C 1 to C 6 alkyl, a halogen, a C 1 to C 6 alkoxy, a C 1 to C 6 haloalkyl, a C 1 to C 6 haloalkoxy, a C 5 to C 6 cycloalkyl, trimethylsilyl (--Si(CH 3 ) 3 ), ##STR58## (wherein Y denotes hydrogen, a halogen, a C 1 to C 6 alkyl, a C 1 to C 6 alkoxy, a C 1 to C 6 haloalkyl, a C 1 to C 6 haloalkoxy or a C 5 to C 6 cycloalkyl, and m is an integer of 1 to 5), n is an integer of 1 to 5, and Z denotes a halogen; said X being the same or different when n is 2 or more, and the alkyls and alkyl moieties contained in the groups being straight or branched.
Claim 17
Independent Claim
191 words
A method for fungicidal, insecticidal, acaricidal, nematocidal treatment in the agricultural and horticultural field with an effective amount of a compound of the formula (I): ##STR57## wherein, R denotes a C 1 to C 6 alkyl, R 1 and R 2 denote each independently hydrogen or a C 1 to C 6 alkyl, X denotes hydrogen, a C 1 to C 6 alkyl, a halogen, a C 1 to C 6 alkoxy, a C 1 to C 6 haloalkyl, a C 1 to C 6 haloalkoxy, a C 5 to C 6 cycloalkyl, trimethylsilyl (--Si(CH 3 ) 3 ), ##STR58## (wherein Y denotes hydrogen, a halogen, a C 1 to C 6 alkyl, a C 1 to C 6 alkoxy, a C 1 to C 6 haloalkyl, a C 1 to C 6 haloalkoxy or a C 5 to C 6 cycloalkyl, and m is an integer of 1 to 5), n is an integer of 1 to 5, and Z denotes a halogen; said X being the same or different when n is 2 or more, and the alkyls and alkyl moieties contained in the groups being straight or branched.
Claim 18
Dependent Claim
43 words
A process according to claim 8, wherein the reaction is carried out in the presence of a hydrogen-absorbing agent selected from sodium carbonate, potassium carbonate and triethylamine at a temperature of from room temperature up to the boiling point of the solvent employed.
Claim 19
Dependent Claim
9 words
The compound of claim 1 of the formula: ##STR59##
Claim 20
Dependent Claim
9 words
The compound of claim 1 of the formula: ##STR60##
Claim 21
Dependent Claim
9 words
The compound of claim 1 of the formula: ##STR61##
Claim 22
Dependent Claim
9 words
The compound of claim 1 of the formula: ##STR62##
Claim 23
Dependent Claim
9 words
The compound of claim 1 of the formula: ##STR63##
Claim 24
Dependent Claim
9 words
The compound of claim 1 of the formula: ##STR64##
Claim 25
Dependent Claim
9 words
The compound of claim 1 of the formula: ##STR65##
Claim 26
Dependent Claim
9 words
The compound of claim 1 of the formula: ##STR66##
Claim 27
Dependent Claim
9 words
The compound of claim 1 of the formula: ##STR67##
Claim 28
Dependent Claim
9 words
The compound of claim 1 of the formula: ##STR68##
Claim 29
Dependent Claim
9 words
The compound of claim 1 of the formula: ##STR69##
Claim 30
Dependent Claim
9 words
The compound of claim 1 of the formula: ##STR70##
Claim 31
Dependent Claim
9 words
The compound of claim 1 of the formula: ##STR71##
Claim 32
Dependent Claim
9 words
The compound of claim 1 of the formula: ##STR72##
Claim 33
Dependent Claim
9 words
The compound of claim 1 of the formula: ##STR73##
Claim 34
Dependent Claim
9 words
The compound of claim 1 of the formula: ##STR74##
Claim 35
Dependent Claim
9 words
The compound of claim 1 of the formula: ##STR75##
Claim 36
Dependent Claim
9 words
The compound of claim 1 of the formula: ##STR76##
Claim 37
Dependent Claim
9 words
The compound of claim 1 of the formula: ##STR77##
Claim 38
Dependent Claim
12 words
A compound according to claim 1, wherein Z is Cl or Br.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-02-17 | 1989-08-19 | 1990-02-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-02-17 | 1993-08-19 | 1994-02-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-02-17 | 1997-08-19 | 1998-02-18 | $7700.00 | Window Closed / Lapsed |