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US4496390A
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N-Phenylpyrazole derivatives
Assignee: May and Baker Ltd
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Filing: 1982-07-15
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Granted: 1985-01-29
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Expires: 2002-07-15
Abstract
Abstract N-Phenylpyrazole derivatives of the formula: <IMAGE> (wherein each of R5 and R6 represents a C1-C4 alkyl or alkoxy radical, a trifluoromethyl, trifluoromethoxy, nitro, cyano or primary amino radical, or a fluorine, chlorine or bromine atom, each of R7, R8 and R9 represents a hydrogen atom, a C1-C4 alkyl or alkoxy radical, a trifluoromethyl, trifluoromethoxy, nitro, cyano or primary amino radical or a fluorine, chlorine or bromine atom, or R5, R7, R8 and R9 each represents a hydrogen atom and R6 represents a trifluoromethoxy or trifluoromethyl radical, and R10 represents a cyano radical or substituted carbamoyl radical -CONHR11, wherein R11 represents a methyl or ethyl radical) have been found to possess useful herbicidal properties. All such N-phenylpyrazole derivatives with the exception of 5-amino-4-cyano-1-(2,4-dichlorophenyl)pyrazole and 5-amino-4-cyano-1-(4-chloro-2-methylphenyl)pyrazole are new compounds. Herbicidal compositions containing such N-phenylpyrazole derivatives are described and also processes for the preparation of the new compounds.
Inventors
- 👤 Leslie R. Hatton
- 👤 Edgar W. Parnell
- 👤 David A. Roberts
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 15:38
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/02; C07D231/10; C07D231/14; C07D231/38; A; A01; A01N; A01N43/00; A01N43/48; A01N43/56; A01N47/00; A01N47/02; A01N47/08; A01N47/10; A01N47/18; A01N47/22; C07C; C07C243/00; C07C255/00; C07D231/40; C07D401/00; C07D401/02; C07D401/04; C07D403/00; C07D403/02; C07D403/04
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
216 words
A method of controlling the growth of weeds at a locus which comprises applying to the locus a herbicidally effective amount of an N-phenylpyrazole derivative in a herbicidal composition which comprises, as active ingredient, an effective amount of an N-phenylpyrazole derivative of the formula: ##STR13## (wherein each of R 5 and R 6 represents an alkyl or alkoxy radical of 1 through 4 carbon atoms, a trifluoromethyl, trifluoromethoxy, nitro, cyano or primary amino radical or a fluorine, chlorine or bomine atom, each of R 7 , R 8 and R 9 represents a hydrogen atom, an alkyl or alkoxy radical of 1 through 4 carbon atoms, a trifluoromethyl, trifluoromethoxy, nitro, cyano or primary amino radical or a fluorine, chlorine or bromine atom, or R 5 , R 7 , R 8 and R 9 each represents a hydrogen atom and R 6 represents a trifluoromethoxy or trifluoromethyl radical and R 10 represents a cyano radical or substituted carbamoyl radical --CONHR 11 , wherein R 11 represents a methyl or ethyl radical), or when at least one of symbols R 5 , R 6 , R 7 , R 8 and R 9 represents a primary amino radical or an agriculturally acceptable acid addition salt thereof, in association with one or more capatible herbicidally-acceptable diluents or carriers.
Claim 2
Independent Claim
216 words
A method of controlling the growth of weeds at a locus which comprises applying to the locus a herbicidally effective amount of an N-phenylpyrazole derivative in a herbicidal composition which comprises, as active ingredient, an effective amount of an N-phenylpyrazole derivative of the formula: ##STR13## (wherein each of R 5 and R 6 represents an alkyl or alkoxy radical of 1 through 4 carbon atoms, a trifluoromethyl, trifluoromethoxy, nitro, cyano or primary amino radical or a fluorine, chlorine or bomine atom, each of R 7 , R 8 and R 9 represents a hydrogen atom, an alkyl or alkoxy radical of 1 through 4 carbon atoms, a trifluoromethyl, trifluoromethoxy, nitro, cyano or primary amino radical or a fluorine, chlorine or bromine atom, or R 5 , R 7 , R 8 and R 9 each represents a hydrogen atom and R 6 represents a trifluoromethoxy or trifluoromethyl radical and R 10 represents a cyano radical or substituted carbamoyl radical --CONHR 11 , wherein R 11 represents a methyl or ethyl radical), or when at least one of symbols R 5 , R 6 , R 7 , R 8 and R 9 represents a primary amino radical or an agriculturally acceptable acid addition salt thereof, in association with one or more capatible herbicidally-acceptable diluents or carriers.
Claim 3
Dependent Claim
52 words
A method according to claim 1 in which the active ingredient is an N-phenylpyrazole derivative of the formula depicted in claim 1 wherein each of R 5 and R 6 represents an alkyl radical of 1 through 4 carbon atoms, a trifluoromethyl or nitro radical, or a fluorine, chlorine or bromine atom.
Claim 4
Dependent Claim
50 words
A method according to claim 1 in which the active ingredient is an N-phenylpyrazole derivative of the formula depicted in claim 1 wherein R 7 represents a hydrogen atom, an alkyl or alkoxy radical of 1 through 4 carbon atoms, a cyano radical or a fluorine, chlorine or bromine atom.
Claim 5
Dependent Claim
41 words
A method according to claim 1 in which the active ingredient is an N-phenylpyrazole derivative of the formula depicted in claim 1 wherein each of R 8 and R 9 represents a hydrogen atom or a fluorine, chlorine or bromine atom.
Claim 6
Dependent Claim
33 words
A method according to claim 1, 2, 3 or 4 in which the active ingredient is an N-phenylpyrazole derivative of the formula depicted in claim 1 wherein R 10 represents a cyano radical.
Claim 7
Dependent Claim
31 words
A method according to claim 1 in which the active ingredient is an N-phenylpyrazole derivative of the formula depicted in claim 1 wherein R 8 and R 9 represent hydrogen atoms.
Claim 8
Dependent Claim
96 words
A method according to claim 1 in which the active ingredient is an N-phenylpyrazole derivative of the formula depicted in claim 1 wherein each of R 5 and R 6 represents an alkyl radical or 1 through 4 carbon atoms, a trifluoromethyl or nitro radical, or a fluorine, chlorine or bromine atom, R 7 represents a hydrogen atom, an alkyl or alkoxy radical of 1 through 4 carbon atoms, a cyano radical, or a fluorine, chlorine or bromine atom, R 8 and R 9 represent hydrogen atoms, and R 10 is as defined in claim 1.
Claim 9
Dependent Claim
77 words
A method according to claim 1 in which the active ingredient is an N-phenylpyrazole derivative of the formula depicted in claim 1 wherein each of R 5 and R 6 represents a methyl, trifluoromethyl or nitro radical or a fluorine, chlorine or bromine atom, R 7 represents a methyl, methoxy or cyano radical or a fluorine, chlorine or bromine atom, R 8 and R 9 represent hydrogen atoms and R 10 is as defined in claim 1.
Claim 10
Dependent Claim
15 words
A method according to claim 7 or 8 wherein R 10 represents a cyano radical.
Claim 11
Dependent Claim
36 words
A method according to claim 1, 2, 3, 4, 6 or 7 wherein the alkyl radicals within the definition of R 5 , R 6 , R 7 , R 8 and R 9 are methyl.
Claim 12
Dependent Claim
36 words
A method according to claim 1, 2, 3, 4, 6 or 7 wherein the alkoxy radicals within the definition of R 5 , R 6 , R 7 , R 8 and R 9 are methoxy.
Claim 13
Dependent Claim
39 words
A method according to claim 1, 2, 3, 4, 6, 7 or 8 in which the active ingredient is an N-phenylpyrazole derivative of the formula depicted in claim 1 wherein R 10 represents a carbamoyl group --CONHCH 3 .
Claim 14
Dependent Claim
43 words
A method according to claim 7 or 8 in which the active ingredient is an N-phenylpyrazole derivative of the formula depicted in claim 1 wherein at least one of the symbols R 5 , R 6 and R 7 represents a chlorine atom.
Claim 15
Dependent Claim
13 words
A method according to claim 1 in which the active ingredient is 5-amino-4-cyano-1-(2,3,4-trichlorophenyl)pyrazole.
Claim 16
Dependent Claim
13 words
A method according to claim 1 in which the active ingredient is 5-amino-4-cyano-1-(2,4-dichlorophenyl)pyrazole.
Claim 17
Dependent Claim
36 words
A method according to claim 1 in which the active ingredient is at least one N-phenylpyrazole derivative selected from 5-amino-1-(2-bromo-3,4-dichlorophenyl)-4-cyanopyrazole, 5-amino-4-cyano-1-(3,4-dichloro-2-methylphenyl)pyrazole, 5-amino-1-(3-bromo-2,4-dichlorophenyl)-4-cyanopyrazole, 5-amino-4-cyano-1-(2,4-dichloro-3-methylphenyl)pyrazole, 5-amino-4-cyano-1-(2,4-dichloro-3-methoxyphenyl)pyrazole, 5-amino-4-cyano-1-(3-cyano-2,4-dichlorophenyl)pyrazole, 5-amino-1-(bromo-2,3-dichlorophenyl)-4-cyanopyrazole, 5-amino-4-cyano-1-(2,3-dichloro-4-methylphenyl)pyrazole, 5-amino-4-cyano-1-(4-bromo-2-chloro-3-methylphenyl)pyrazole, 5-amino-4-cyano-1-(2-chloro-3,4-dimethylphenyl)pyrazole, 5-amino-4-cyano-1-(2-chloro-3-cyano-4-methylphenyl)pyrazole, 5-amino-1-(3-chloro-2,4-dibromophenyl)-4-cyanopyrazole, 5-amino-1-(3-chloro-2,4-dimethylphenyl)-4-cyanopyrazole, 5-amino-1-(2-bromo-4-chloro-3-methylphenyl)-4-cyanopyrazole, 5-amino-1-(4-chloro-2,3-dimethylphenyl)-4-cyanopyrazole and 5-amino-1-(4-chloro-3-cyano-2-methylphenyl)-4-cyanopyrazole.
Claim 18
Dependent Claim
38 words
A method according to claim 1 in which the active ingredient is at least one N-phenylpyrazole derivative selected from 5-amino-4-cyano-1-(2,6-dichloro-4-ethylphenyl)pyrazole, 5-amino-1-(2-chloro-4-ethylphenyl)-4-cyanopyrazole, 5-amino-4-cyano-1-(4-methyl-2,3,5,6-tetrafluorophenyl)pyrazole, 5-amino-1-(2-chloro-4-methylphenyl)-4-cyanopyrazole, 5-amino-4-cyano-1-(4-methyl-2,3,6-trichlorophenyl)pyrazole, 5-amino-1-(4-n-butyl-2,3,5,6-tetrafluorophenyl)-4-cyanopyrazole, 5-amino-1-(2-chloro-4-isopropylphenyl)-4-cyanopyrazole, 5-amino-4-cyano-1-(2,3-dichloro-4-ethylphenyl)pyrazole, 5-amino-4-cyano-1-(4-ethyl-2,3,5,6-tetrafluorophenyl)pyrazole, 5-amino-1-(2-chloro-4-n-propylphenyl)-4-cyanopyrazole, 5-amino-4-cyano-1-(2,6-dibromo-4-trifluoromethylphenyl)pyrazole, 5-amino-4-cyano-1-(3,5-difluoro-2,4,6-trichlorophenyl)pyrazole, 5-amino-4-cyano-1-(2,4-dichloro-6-methylphenyl)pyrazole, 5-amino-1-(4-bromo-2,3,5,6-tetrafluorophenyl)-4-cyanopyrazole, 5-amino-1-(4-chloro-2,3,5,6-tetrafluorophenyl)-4-cyanopyrazole, 5-amino-1-(2-bromo-4-trifluoromethylphenyl)-4-cyanopyrazole, 5-amino-1-(4-sec-butyl-2,3,5,6-tetrafluorophenyl)-4-cyanopyrazole and 5-amino-4-cyano-1-(2,3,4,6-tetrachlorophenyl)pyrazole.
Claim 19
Dependent Claim
23 words
A method according to claim 1 in which the herbicidal composition comprises from 0.05 to 90% by weight of the said N-phenylpyrazole derivative.
Claim 20
Dependent Claim
130 words
A method according to claim 8 in which the weeds are broad-leafed weeds, selected from the group consisting of Aethusa cynapium, Abutilon theophrasti, Amaranthus retroflexus, Amsinckia intermedia, Anagallis arvensis, Anthemis arvensis, Atriplex patula, Bidens pilosa, Brassica nigra, Capsella bursa-pastoris, Chenopodium album, Chrysanthemum segetum, Cirsium arvense, Datura stamonium, Desmodium tortuosum, Emex australis, Euphorbia helioscopia, Fumaria officinalis, Galeopsis tetrahit, Galium aparine, Geranium dissectum, Ipomea purpurea, Lamium purpureum, Lapsana communis, Matricaria inodora, Monochoria vaginalis, Papaver rhoeas, Physalis longifolia, Plantago lanceolata, Polygonum spp.,(eg. Polygonum aviculare, Polygonum convolvulus and Polygonum persicaria), Portulaca oleracea, Raphanusraphanistrum, Rotala indica, Rumex obtusifolius, Saponaria vaccaria, Scandix pectenveneris, Senecio vulgaris, Sesbania florida, Sida spinosa, Silene alba, Sinapis arvensis, Solanum nigrum, Sonchus arvensis, Spergula arvensis, Stellaria media, Thlaspi arvense, Tribulus terrestria, Urtica urens, Veronica hederifolia, Veronica persica, Viola arvensis and Xanthium strumarium.
Claim 21
Dependent Claim
50 words
A method according to claim 1 in which the weeds are grass weeds, selected from the group consisting of Alopecurus myosuroides, Apera spica-venti, Agrostis stolonifera, Avena fatua, Avena ludoviciana, Brachiaria spp., Bromus sterilis, Bromus tectorum, Cenchrus spp., Cynodon dactylon, Digitaria sanguinalis, Echinochloa crus-galli, Eleusine indica, Setaria viridis and Sorghum halepense.
Claim 22
Dependent Claim
21 words
A method according to claim 1, 19 or 20 wherein the N-phenylpyrazole derivative is applied pre- or post-emergence of the weeds.
Claim 23
Dependent Claim
24 words
A method according to claim 1 in which the herbicidal composition is applied to an area used, or to be used, for growing crops.
Claim 24
Dependent Claim
35 words
A method according to claim 22 in which the herbicidal composition is applied to a crop-growing area at a rate sufficient to control the growth of weeds without causing, substantial permanent damage to the crop.
Claim 25
Dependent Claim
24 words
A method according to claim 1 in which the N-phenylpyrazole derivative is applied at a rate between 0.1 kg and 20 kg per hectare.
Claim 26
Dependent Claim
39 words
A method according to claim 22 or 23 in which the crop is a cereal, soya beans, field or dwarf beans, peas, lucerne, cotton, peanuts, flax, onions, carrots, cabbage, oilseed rape, sunflower, sugar beet, or permanent or sown grassland.
Claim 27
Dependent Claim
19 words
A method according to claim 22 or 23 in which the crop is wheat, barley, oats, maize or rice.
Claim 28
Dependent Claim
24 words
A method according to claim 22 in which the N-phenylpyrazole derivative is applied at a rate between 0.25 kg and 8.0 kg per hectare.
Claim 29
Dependent Claim
26 words
A method according to claim 24 or 27 in which the N-phenylpyrazole derivative is applied at a rate between 0.5 kg and 2.0 kg per hectare.
Claim 30
Dependent Claim
38 words
A method according to claim 27 in which the herbicidal composition is applied for the control of broad-leafed weeds in an area used for growing a cereal crop before or after emergence of both the crop and weeds.
Claim 31
Dependent Claim
18 words
A method according to claim 29 in which the herbicidal composition is applied post-emergence of the broad-leafed weeds.
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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) | 1988-01-29 | 1988-07-30 | 1989-01-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-01-29 | 1992-07-30 | 1993-01-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-01-29 | 1996-07-30 | 1997-01-29 | $7700.00 | Window Closed / Lapsed |