EP0044209A1
Expired / Lapsed
EP
⏱️ 0.0 years remaining
Herbicidal sulfonamides
Assignee: EIDP Inc
•
Filing: 1981-07-10
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Granted: —
•
Expires: 2001-07-10
Abstract
Abstract Sulfonamide derivatives of the formula wherein R is H, halogen, nitro, CF 3 , alkyl or alkoxy; R, is H, Cl or alkyl; R 2 is H or CH 3 : L is Cl, Br, CN, OH or a variety of organic groups; R 8 is H. CH 3 or OCH 3 ; W is O or S; A is X is H, Cl, Br or various organic groups: Y is CH 3 or OCH 3 : Z is N or optionally substituted CH; Y' is H. CH 3 , OCH 3 or OCH 2 CH 3 ; and Q is 0 or CH 2 ; and their salts, exhibit herbicidal and plant growth regulant activities.. They may be formulated for use in conventional manner. The compound may be made e.g. by reacting a novel sulfonyl isocyanate of general formula with the appropriate 2-aminoheterocycle of formula A-NHR 8, or alternatively by displacing one or both chlorine atoms in the heterocyclic moiety of a novel sulfonylurea of general formula by the appropriate alkoxy groups. Further methods of preparation are also disclosed.
Inventors
- 👤 William Brown Farnham
- 👤 George Levitt
- 👤 Gregory Wayne Schwing
- 👤 Richard Frank Sauers
- 👤 Wallace Christian Petersen
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-05 10:58
CPC Classifications
C; C07; C07C; C07C309/00; C07C309/78; C07C309/86; C07C309/89; A; A01; A01N; A01N47/00; A01N47/08; A01N47/28; A01N47/36; C07C311/00; C07C311/65; C07C323/00; C07D; C07D295/00; C07D295/04; C07D295/08; C07D295/096; C07D521/00
Claims Analysis
Total Claims: 279
Claim 1
Independent Claim
166 words
A compound selected from: wherein L is CO 2 R 10 , CONR 3 R 4 CN, + Cl, Br, NR 3 R 4 , NR 3 R 4 R 4 ', N(R 4 )C(O)R 5 , N(R 4 )C(O)NHR 6 , N(R 4 )C(O)OR 7 , S(O) n R 7 , OR 9 , SO 2 NR 3 R 4 , OH,OC(O)R 11 , OC(O)NHR 12 or OC(O)OR 13 ; R is H, F, Cl, Br, NO 2 , CF 3 , C 1 -C 3 alkyl or C 1 -C 3 alkoxy; R 1 is H; C l or C 1 -C 4 alkyl; R 2 is H or CH 3 ; R3 is H , C 1 -C 4 alkyl or OCH 3 ; R 4 is H or C 1 -C 4 alkyl; R 3 and R 4 can be taken together to form -(CH 2 ) 4 -, -(CH 2 ) 5 - or -(CH 2 CH 2 ) 2 O;
Claim 2
Dependent Claim
166 words
A compound selected from: wherein L is CO 2 R 10 , CONR 3 R 4 CN, + Cl, Br, NR 3 R 4 , NR 3 R 4 R 4 ', N(R 4 )C(O)R 5 , N(R 4 )C(O)NHR 6 , N(R 4 )C(O)OR 7 , S(O) n R 7 , OR 9 , SO 2 NR 3 R 4 , OH,OC(O)R 11 , OC(O)NHR 12 or OC(O)OR 13 ; R is H, F, Cl, Br, NO 2 , CF 3 , C 1 -C 3 alkyl or C 1 -C 3 alkoxy; R 1 is H; C l or C 1 -C 4 alkyl; R 2 is H or CH 3 ; R3 is H , C 1 -C 4 alkyl or OCH 3 ; R 4 is H or C 1 -C 4 alkyl; R 3 and R 4 can be taken together to form -(CH 2 ) 4 -, -(CH 2 ) 5 - or -(CH 2 CH 2 ) 2 O;
Claim 3
Dependent Claim
3 words
TEST G NUTSEDGE
Claim 4
Dependent Claim
3 words
TEST G NUTSEDGE
Claim 5
Dependent Claim
2 words
Test G
Claim 6
Dependent Claim
2 words
Test G
Claim 7
Dependent Claim
190 words
Purple nutsedge (Cyoerus rotundus) tubers were planted about 2 cm deep in Fallsington silt loam soil contained in 10 cm diameter plastic pots. Five tubers were planted in each pot. Compounds of this invention were dissolved in a non-phytotoxic diluent and sprayed at 560 1/ha in four methods of application: soil surface, tuber/soil, soil incorporated and post-emergence. The soil surface spray consisted of spraying the compound on the surface of the firmed covering soil. The tuber/soil spray consisted of spraying the compound on exposed tubers and subtending soil before adding the untreated covering soil. Soil incorporated treatment consisted in mixing the compound with the covering soil before using it to cover the tubers. The post-emergence treatment was sprayed on nutsedge foliage and the surrounding soil surface when nutsedge had emerged and grown to a height of about 12 cm. Pots receiving the post-emergence treatments were placed directly in the greenhouse. Pots receiving the other treatments were misted with about 0.3 cm water before being transferred to the greenhouse. Response ratings assessed after four weeks are recorded in Table G based on the same rating system as described in procedure A.
Claim 8
Dependent Claim
190 words
Purple nutsedge (Cyoerus rotundus) tubers were planted about 2 cm deep in Fallsington silt loam soil contained in 10 cm diameter plastic pots. Five tubers were planted in each pot. Compounds of this invention were dissolved in a non-phytotoxic diluent and sprayed at 560 1/ha in four methods of application: soil surface, tuber/soil, soil incorporated and post-emergence. The soil surface spray consisted of spraying the compound on the surface of the firmed covering soil. The tuber/soil spray consisted of spraying the compound on exposed tubers and subtending soil before adding the untreated covering soil. Soil incorporated treatment consisted in mixing the compound with the covering soil before using it to cover the tubers. The post-emergence treatment was sprayed on nutsedge foliage and the surrounding soil surface when nutsedge had emerged and grown to a height of about 12 cm. Pots receiving the post-emergence treatments were placed directly in the greenhouse. Pots receiving the other treatments were misted with about 0.3 cm water before being transferred to the greenhouse. Response ratings assessed after four weeks are recorded in Table G based on the same rating system as described in procedure A.
Claim 9
Dependent Claim
2 words
Test F
Claim 10
Dependent Claim
2 words
Test F
Claim 11
Dependent Claim
97 words
A test sample of compound 8 was formulated and applied directly to the water of simulated paddies, three days after transplanting of rice. The paddies were maintained in a greenhouse, and plant response ratings were taken one week and four weeks after application. Reference to the table above indicates that rice tolerated the application of the test sample at 500 g ai/ha, whereas the important weed (in rice culture in some areas) water chestnut was completely controlled. Arrowhead, which also is an important weed in some rice culture areas, was partially controlled at the same application rate.
Claim 12
Dependent Claim
97 words
A test sample of compound 8 was formulated and applied directly to the water of simulated paddies, three days after transplanting of rice. The paddies were maintained in a greenhouse, and plant response ratings were taken one week and four weeks after application. Reference to the table above indicates that rice tolerated the application of the test sample at 500 g ai/ha, whereas the important weed (in rice culture in some areas) water chestnut was completely controlled. Arrowhead, which also is an important weed in some rice culture areas, was partially controlled at the same application rate.
Claim 13
Dependent Claim
2 words
TEST E
Claim 14
Dependent Claim
2 words
TEST E
Claim 15
Dependent Claim
38 words
Test samples were formulated and applied directly to the water of paddies three days after transplanting of Japonica rice. The paddies were maintained in a greenhouse, and plant response ratings were taken one and three weeks after application.
Claim 16
Dependent Claim
38 words
Test samples were formulated and applied directly to the water of paddies three days after transplanting of Japonica rice. The paddies were maintained in a greenhouse, and plant response ratings were taken one and three weeks after application.
Claim 17
Dependent Claim
2 words
Test 0
Claim 18
Dependent Claim
2 words
Test 0
Claim 19
Dependent Claim
154 words
Two ten-inch in diameter plastic pans lined with polyethylene liners were filled with prepared Fallsington silt loam soil. One pan was planted with seecs of wheat (Triticum aestivum), barley (Hordeur vulgare), wild oats (Avena fatua), downy brome (Bromus tectorum), cheatgrass (Bromus secalinus), blackgrass (Alcoecurus myosuroides), annual bluegrass (Poa annua), green foxtail (Setaria viridis), quackgrass (Agropyron repens), Italian ryegrass (Lolium multi- ficrum) and ripgut brome (Bromus riqidus). The other pan was planted with seeds of Russian thistle (Salsole kali), tansy mustard (Descuraina pinnata), smartweed (Polygonun pennsylvanicum), tumble mustard (Sistbriu- altissiur) kochia (Kochia scoparia), shepherd's purse (Caosella bursa-pastoris), Matricaria inodora, black nightshade (Solanum niorum), yellow rocket (Barbarea vulcaris), wild mustard (Brassica kaber) and wild buckwheat (Polygonum convolvulus). The above two pans were treated pre-emergence. At the same time two pens in which the above plant species were growing were treated post-emergence. Plant height at the time of treatment ranged from 1-15 cm depending on plant species.
Claim 20
Dependent Claim
154 words
Two ten-inch in diameter plastic pans lined with polyethylene liners were filled with prepared Fallsington silt loam soil. One pan was planted with seecs of wheat (Triticum aestivum), barley (Hordeur vulgare), wild oats (Avena fatua), downy brome (Bromus tectorum), cheatgrass (Bromus secalinus), blackgrass (Alcoecurus myosuroides), annual bluegrass (Poa annua), green foxtail (Setaria viridis), quackgrass (Agropyron repens), Italian ryegrass (Lolium multi- ficrum) and ripgut brome (Bromus riqidus). The other pan was planted with seeds of Russian thistle (Salsole kali), tansy mustard (Descuraina pinnata), smartweed (Polygonun pennsylvanicum), tumble mustard (Sistbriu- altissiur) kochia (Kochia scoparia), shepherd's purse (Caosella bursa-pastoris), Matricaria inodora, black nightshade (Solanum niorum), yellow rocket (Barbarea vulcaris), wild mustard (Brassica kaber) and wild buckwheat (Polygonum convolvulus). The above two pans were treated pre-emergence. At the same time two pens in which the above plant species were growing were treated post-emergence. Plant height at the time of treatment ranged from 1-15 cm depending on plant species.
Claim 21
Dependent Claim
96 words
The compounds applied were diluted with a non-phytotoxic solvent and sprayed over-the-top of the pans. An untreated control and a solvent alone control were included for comparison. All treatments were maintained in the greenhouse for 20 days at which time the treatments were compared to the controls and the effects visually rated. in accordance with the rating system described for Test A. The recorded data are presented in Table D. The data indicate that certain compounds from within the scope of this invention have utility for weed control in cereal crops, such as wheat and barley.
Claim 22
Dependent Claim
96 words
The compounds applied were diluted with a non-phytotoxic solvent and sprayed over-the-top of the pans. An untreated control and a solvent alone control were included for comparison. All treatments were maintained in the greenhouse for 20 days at which time the treatments were compared to the controls and the effects visually rated. in accordance with the rating system described for Test A. The recorded data are presented in Table D. The data indicate that certain compounds from within the scope of this invention have utility for weed control in cereal crops, such as wheat and barley.
Claim 23
Dependent Claim
2 words
Test C
Claim 24
Dependent Claim
2 words
Test C
Claim 25
Dependent Claim
135 words
Twenty-five cm diameter plastic pots filled with Fallsington silt loam were planted with soybeans, cotton, alfalfa, corn, rice, wheat, sorghum, velvetleaf (Abutilon theophrasti), sesbania (Sesbania exaltata), Cassia (Cassia tora), morningglory (Ioomoea hederacea), jimsonweed (Datura stramonium), cocklebur (xanthium pennsylvanicum), crabgrass (Digitaria spp.), nutsedge (Cyperus rotundus), barnyardgrass (Echino- chlos crusgalli), giant foxtail (Setaria faberii) and wild oats (Avena fatua). Approximately two weeks after planting, the young plants and the soil around them were sprayed overall with the test chemicals dissolved in a non-phytotoxic solvent. Two weeks after treatment, all species were compared to untreated controls and visually rated for response to treatment. The rating system was as described previously for Test A. Tne data are presented in Table C. Several of the compounds tested by this procedure are useful for the post-emergence control of weeds in wheat.
Claim 26
Dependent Claim
135 words
Twenty-five cm diameter plastic pots filled with Fallsington silt loam were planted with soybeans, cotton, alfalfa, corn, rice, wheat, sorghum, velvetleaf (Abutilon theophrasti), sesbania (Sesbania exaltata), Cassia (Cassia tora), morningglory (Ioomoea hederacea), jimsonweed (Datura stramonium), cocklebur (xanthium pennsylvanicum), crabgrass (Digitaria spp.), nutsedge (Cyperus rotundus), barnyardgrass (Echino- chlos crusgalli), giant foxtail (Setaria faberii) and wild oats (Avena fatua). Approximately two weeks after planting, the young plants and the soil around them were sprayed overall with the test chemicals dissolved in a non-phytotoxic solvent. Two weeks after treatment, all species were compared to untreated controls and visually rated for response to treatment. The rating system was as described previously for Test A. Tne data are presented in Table C. Several of the compounds tested by this procedure are useful for the post-emergence control of weeds in wheat.
Claim 27
Dependent Claim
33 words
Twenty-eight days after treatment, the plants were evaluated and visually rated for response to the chemical treatments utilizing the rating system described previously for Test A. The data are summarized in Table B.
Claim 28
Dependent Claim
33 words
Twenty-eight days after treatment, the plants were evaluated and visually rated for response to the chemical treatments utilizing the rating system described previously for Test A. The data are summarized in Table B.
Claim 29
Dependent Claim
2 words
Test B
Claim 30
Dependent Claim
2 words
Test B
Claim 31
Dependent Claim
146 words
Two plastic bulb pans were filled with fertilized and limed Fallsington silt loam soil. One pan was planted with corn, sorghum, Kentucky bluegrass and several grassy weeds. The other pan was planted with cotton, soybeans, purple nutsedge (Cyoerus rotundus), and several broadleaf weeds. The following grassy and broadleaf weeds were planted: crabgrass (Diaitaria sanguinalis), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), johnsongrass (Sorohum hale- pense), dallisgrass (Pas p alum dilatatum), giant foxtail (Setaria faberii), cheatgrass (Bromus secalinus), mustard (Brassica arvensis), cocklebur (Xanthium pensylvanicum) , pigweed (Amaranthus retroflexus), morningglory (Ipomoea hederacea), cassia (Cassia tora), teaweed (Sida soinosa), velvetleaf (Abutilon theophrasti), and jimsonweed (Datura stramonium). A 12.5 cm diameter plastic pot was also filled with prepared soil and planted with rice and wheat. Another 12.5 cm pot was planted with sugarbeets. The above four containers were treated pre-emergence with several test compounds within the scope of the invention.
Claim 32
Dependent Claim
146 words
Two plastic bulb pans were filled with fertilized and limed Fallsington silt loam soil. One pan was planted with corn, sorghum, Kentucky bluegrass and several grassy weeds. The other pan was planted with cotton, soybeans, purple nutsedge (Cyoerus rotundus), and several broadleaf weeds. The following grassy and broadleaf weeds were planted: crabgrass (Diaitaria sanguinalis), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), johnsongrass (Sorohum hale- pense), dallisgrass (Pas p alum dilatatum), giant foxtail (Setaria faberii), cheatgrass (Bromus secalinus), mustard (Brassica arvensis), cocklebur (Xanthium pensylvanicum) , pigweed (Amaranthus retroflexus), morningglory (Ipomoea hederacea), cassia (Cassia tora), teaweed (Sida soinosa), velvetleaf (Abutilon theophrasti), and jimsonweed (Datura stramonium). A 12.5 cm diameter plastic pot was also filled with prepared soil and planted with rice and wheat. Another 12.5 cm pot was planted with sugarbeets. The above four containers were treated pre-emergence with several test compounds within the scope of the invention.
Claim 33
Dependent Claim
2 words
Compound 19
Claim 34
Dependent Claim
2 words
Compound 19
Claim 35
Dependent Claim
2 words
Compound 20
Claim 36
Dependent Claim
2 words
Compound 20
Claim 37
Dependent Claim
2 words
Comnound 21
Claim 38
Dependent Claim
2 words
Comnound 21
Claim 39
Dependent Claim
2 words
Compound 15
Claim 40
Dependent Claim
2 words
Compound 15
Claim 41
Dependent Claim
2 words
Compound 16
Claim 42
Dependent Claim
2 words
Compound 16
Claim 43
Dependent Claim
2 words
Compound 17
Claim 44
Dependent Claim
2 words
Compound 17
Claim 45
Dependent Claim
2 words
Compound 18
Claim 46
Dependent Claim
2 words
Compound 18
Claim 47
Dependent Claim
2 words
Compound 11
Claim 48
Dependent Claim
2 words
Compound 11
Claim 49
Dependent Claim
2 words
Compound 12
Claim 50
Dependent Claim
2 words
Compound 12
Claim 51
Dependent Claim
2 words
Compound 13
Claim 52
Dependent Claim
2 words
Compound 13
Claim 53
Dependent Claim
2 words
Compound 14
Claim 54
Dependent Claim
2 words
Compound 14
Claim 55
Dependent Claim
2 words
Compound 7
Claim 56
Dependent Claim
2 words
Compound 7
Claim 57
Dependent Claim
2 words
Compound 8
Claim 58
Dependent Claim
2 words
Compound 8
Claim 59
Dependent Claim
2 words
Compound 9
Claim 60
Dependent Claim
2 words
Compound 9
Claim 61
Dependent Claim
2 words
Compound 10
Claim 62
Dependent Claim
2 words
Compound 10
Claim 63
Dependent Claim
2 words
Compound 4
Claim 64
Dependent Claim
2 words
Compound 4
Claim 65
Dependent Claim
2 words
Compound 5
Claim 66
Dependent Claim
2 words
Compound 5
Claim 67
Dependent Claim
2 words
Compound 6
Claim 68
Dependent Claim
2 words
Compound 6
Claim 69
Dependent Claim
2 words
Compound 1
Claim 70
Dependent Claim
2 words
Compound 1
Claim 71
Dependent Claim
2 words
Compound 2
Claim 72
Dependent Claim
2 words
Compound 2
Claim 73
Dependent Claim
2 words
Compound 3
Claim 74
Dependent Claim
2 words
Compound 3
Claim 75
Dependent Claim
2 words
Test A
Claim 76
Dependent Claim
2 words
Test A
Claim 77
Dependent Claim
154 words
Seeds of crabgrass (Di g itaria spp.), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), cassia (Cassia tora), morningglory (Ipomoea Sp.), cocklebur (Xanthium spp.), sorghum, corn, soybean, rice, wheat and nutsedge tubers (Cyperus r otundus) were planted in a growth medium and treated p r e-emergence with the chemicals dissolved in a non-phytotoxic solvent. At the same time, cotton having five leaves (including cotyledonary ones), bush beans with the second trifoliate leaf expanding, crabgrass and barnyardgrass with two leaves, wild oats with one leaf, cassia with three leaves (including cotyledonary ones), morningglory and cocklebur with four leaves (including the cotyledonary ones), sorghum and corn with three leaves, soybean with two cotyledonary leaves, rice with two leaves, wheat with two leaves, and nutsedge with three to five leaves were sprayed. Treated plants and controls were maintained in a greenhouse for sixteen days, then all species were compared to controls and visually rated for response to treatment.
Claim 78
Dependent Claim
154 words
Seeds of crabgrass (Di g itaria spp.), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), cassia (Cassia tora), morningglory (Ipomoea Sp.), cocklebur (Xanthium spp.), sorghum, corn, soybean, rice, wheat and nutsedge tubers (Cyperus r otundus) were planted in a growth medium and treated p r e-emergence with the chemicals dissolved in a non-phytotoxic solvent. At the same time, cotton having five leaves (including cotyledonary ones), bush beans with the second trifoliate leaf expanding, crabgrass and barnyardgrass with two leaves, wild oats with one leaf, cassia with three leaves (including cotyledonary ones), morningglory and cocklebur with four leaves (including the cotyledonary ones), sorghum and corn with three leaves, soybean with two cotyledonary leaves, rice with two leaves, wheat with two leaves, and nutsedge with three to five leaves were sprayed. Treated plants and controls were maintained in a greenhouse for sixteen days, then all species were compared to controls and visually rated for response to treatment.
Claim 79
Dependent Claim
88 words
The ratings, shown in Table A, are based on a numerical scale extending from 0 = no injury, to 10 = complete kill. The accompanying descriptive symbols have the following meanings: diphenylacetamide (diphenamide); 2,4-dichlorophenoxyacetic acid (2,4-d) (and closely related compounds); 4-chloro-2-butynyl-3-chlorophenilcarbamate (barban); S-(2,3-dichloroallyl)diisopropylthiocarbamate (diallate); S-(2,3,3-trichloroallyl)diisopropyl- thiocarbamate (triallate); 1,2-dimethyl-3,5-diphenyl-1H-pyrazolium methyl sulfate (difenzoquat methyl sulfate); methyl 2-[4-(2,4-dichlorophenoxy)-phenoxy]propanoate (diclofop methyl); 4-amino-6-tert-butyl-3-methylthio)-1,2,4-triazin-5(4H)one (metri- buzin); 3-(3,4-dichlorophenyl)-1-methoxy-1-methylures (linuron); 3-isopropyl-1H-2,1,3-benzothiodiazin-4(3H)-one-2,2-dioxide (bentazon); α,α,α-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine (trifluralin); 1,1'-dimethyl-4,4'-bipyridinium ion (paraquat); monosodium methanearsonate (MSMA); 2-chloro-2' , 6'-diethyl(methoxymethythyl) acetanilide (alachlor); and 1,1-dimethyl-3-(α,α,α-trifluror-m-tolyl)urea (fluometuron), and 5-[2-chloro-4-(trifluoromethyl) phenoxy-2-nitrobenzoic acid, methyl ester (acifluorfen, methyl).
Claim 80
Dependent Claim
88 words
The ratings, shown in Table A, are based on a numerical scale extending from 0 = no injury, to 10 = complete kill. The accompanying descriptive symbols have the following meanings: diphenylacetamide (diphenamide); 2,4-dichlorophenoxyacetic acid (2,4-d) (and closely related compounds); 4-chloro-2-butynyl-3-chlorophenilcarbamate (barban); S-(2,3-dichloroallyl)diisopropylthiocarbamate (diallate); S-(2,3,3-trichloroallyl)diisopropyl- thiocarbamate (triallate); 1,2-dimethyl-3,5-diphenyl-1H-pyrazolium methyl sulfate (difenzoquat methyl sulfate); methyl 2-[4-(2,4-dichlorophenoxy)-phenoxy]propanoate (diclofop methyl); 4-amino-6-tert-butyl-3-methylthio)-1,2,4-triazin-5(4H)one (metri- buzin); 3-(3,4-dichlorophenyl)-1-methoxy-1-methylures (linuron); 3-isopropyl-1H-2,1,3-benzothiodiazin-4(3H)-one-2,2-dioxide (bentazon); α,α,α-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine (trifluralin); 1,1'-dimethyl-4,4'-bipyridinium ion (paraquat); monosodium methanearsonate (MSMA); 2-chloro-2' , 6'-diethyl(methoxymethythyl) acetanilide (alachlor); and 1,1-dimethyl-3-(α,α,α-trifluror-m-tolyl)urea (fluometuron), and 5-[2-chloro-4-(trifluoromethyl) phenoxy-2-nitrobenzoic acid, methyl ester (acifluorfen, methyl).
Claim 81
Dependent Claim
20 words
The activity of these compounds was discovered in greenhouse tests. The test procedures are described and the data shown below.
Claim 82
Dependent Claim
20 words
The activity of these compounds was discovered in greenhouse tests. The test procedures are described and the data shown below.
Claim 83
Dependent Claim
1 words
Utility
Claim 84
Dependent Claim
1 words
Utility
Claim 85
Dependent Claim
84 words
The compounds of the present invention are active herbicides. They have utility for broadspectrum pre- and/or post-emergence weed control in areas where com- plete control of all vegetation is desired, such as around fuel storage tanks, ammunition depots, industrial storage areas, oil well sites, drive-in theaters, around billboards, highway and railroad structures. By properly selecting rate and time of application, compounds of this invention may be used to modify plant growth beneficially, and also selectively control weeds in crops such as wheat and barley.
Claim 86
Dependent Claim
84 words
The compounds of the present invention are active herbicides. They have utility for broadspectrum pre- and/or post-emergence weed control in areas where com- plete control of all vegetation is desired, such as around fuel storage tanks, ammunition depots, industrial storage areas, oil well sites, drive-in theaters, around billboards, highway and railroad structures. By properly selecting rate and time of application, compounds of this invention may be used to modify plant growth beneficially, and also selectively control weeds in crops such as wheat and barley.
Claim 87
Dependent Claim
119 words
The precise amount of the compound of Formula I to be used in any given situation will vary according to the particular end result desired, the amount of foliage present, the weeds to be controlled, the soil type, the formulation and mode of application, weather conditions, etc. Since so many variables play a role, it is not possible to state a rate of application suitable for all situations. Broadly speaking, the compounds of this invention are used at levels of about 0.001 to 20 kg/ha with a preferred range of 0.01 to 10 kg/ha. In general, the higher rates of application from within this range will be selected for adverse conditions or where extended persistence in soil is desired.
Claim 88
Dependent Claim
119 words
The precise amount of the compound of Formula I to be used in any given situation will vary according to the particular end result desired, the amount of foliage present, the weeds to be controlled, the soil type, the formulation and mode of application, weather conditions, etc. Since so many variables play a role, it is not possible to state a rate of application suitable for all situations. Broadly speaking, the compounds of this invention are used at levels of about 0.001 to 20 kg/ha with a preferred range of 0.01 to 10 kg/ha. In general, the higher rates of application from within this range will be selected for adverse conditions or where extended persistence in soil is desired.
Claim 89
Dependent Claim
43 words
The compounds of Formula I may be combined with other herbicides and are particularly useful in combination with ureas such as 3-(3,4-dichlorophenyl)-1,1-dimethylurea (diuron); the triazines such as 2-chloro-4-(ethyl- amino)-6-(isopropylamino)-s-triazine (atrazine); the uracils such as 5-bromo-3-sec-butyl-6-methyluracil (bromacil); N- (phosponomethyl) glycine (glyphosate); 3-cyclohexyl-1-methyl-6-dimethylamino-s-trinzine-2,4(1H,3H)-dione (hexazinone): N,N-dimethyl-2,2-
Claim 90
Dependent Claim
43 words
The compounds of Formula I may be combined with other herbicides and are particularly useful in combination with ureas such as 3-(3,4-dichlorophenyl)-1,1-dimethylurea (diuron); the triazines such as 2-chloro-4-(ethyl- amino)-6-(isopropylamino)-s-triazine (atrazine); the uracils such as 5-bromo-3-sec-butyl-6-methyluracil (bromacil); N- (phosponomethyl) glycine (glyphosate); 3-cyclohexyl-1-methyl-6-dimethylamino-s-trinzine-2,4(1H,3H)-dione (hexazinone): N,N-dimethyl-2,2-
Claim 91
Dependent Claim
3 words
Example 79 Granule
Claim 92
Dependent Claim
3 words
Example 79 Granule
Claim 93
Dependent Claim
106 words
The ingredients are blended and milled to pass through a 100 mesh screen. This material is then added to a fluid bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized material. The fluidization and spraying are continued until granules of the desired size range are made. The spraying is stopped, but fluidization is continued, optionally with heat, until the water constant is reduced to the desired level., generally less than 1%. The material is then discharged, screened to the desired size range, generally 14-100 mesh (1410-149 microns), and packaged for use. :
Claim 94
Dependent Claim
106 words
The ingredients are blended and milled to pass through a 100 mesh screen. This material is then added to a fluid bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized material. The fluidization and spraying are continued until granules of the desired size range are made. The spraying is stopped, but fluidization is continued, optionally with heat, until the water constant is reduced to the desired level., generally less than 1%. The material is then discharged, screened to the desired size range, generally 14-100 mesh (1410-149 microns), and packaged for use. :
Claim 95
Dependent Claim
2 words
Example 80
Claim 96
Dependent Claim
2 words
Example 80
Claim 97
Dependent Claim
2 words
Wettable Powder
Claim 98
Dependent Claim
2 words
Wettable Powder
Claim 99
Dependent Claim
27 words
The ingredients are thoroughly blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size. The material is reblended and then packaged.
Claim 100
Dependent Claim
27 words
The ingredients are thoroughly blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size. The material is reblended and then packaged.
Claim 101
Dependent Claim
2 words
Example 77
Claim 102
Dependent Claim
2 words
Example 77
Claim 103
Dependent Claim
2 words
Oil Suspension
Claim 104
Dependent Claim
2 words
Oil Suspension
Claim 105
Dependent Claim
40 words
The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water.
Claim 106
Dependent Claim
40 words
The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water.
Claim 107
Dependent Claim
2 words
Example 78
Claim 108
Dependent Claim
2 words
Example 78
Claim 109
Dependent Claim
2 words
Aqueous Suspension
Claim 110
Dependent Claim
2 words
Aqueous Suspension
Claim 111
Dependent Claim
22 words
The ingredients are blended and ground together in a sand mill to produce particles essentially all , under 5 microns in size.
Claim 112
Dependent Claim
22 words
The ingredients are blended and ground together in a sand mill to produce particles essentially all , under 5 microns in size.
Claim 113
Dependent Claim
2 words
Example 74
Claim 114
Dependent Claim
2 words
Example 74
Claim 115
Dependent Claim
3 words
High Strength Concentrate
Claim 116
Dependent Claim
3 words
High Strength Concentrate
Claim 117
Dependent Claim
32 words
The ingredients are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening) The concentrate may be formulated further if necessary.
Claim 118
Dependent Claim
32 words
The ingredients are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening) The concentrate may be formulated further if necessary.
Claim 119
Dependent Claim
2 words
Example 75
Claim 120
Dependent Claim
2 words
Example 75
Claim 121
Dependent Claim
2 words
Wettable Powder
Claim 122
Dependent Claim
2 words
Wettable Powder
Claim 123
Dependent Claim
30 words
The ingredients are blended and ground in a hammer-mill to produce particles essentially all below 100 microns. The material is sifted through a U.S.S. No. SO screen and then packaged.
Claim 124
Dependent Claim
30 words
The ingredients are blended and ground in a hammer-mill to produce particles essentially all below 100 microns. The material is sifted through a U.S.S. No. SO screen and then packaged.
Claim 125
Dependent Claim
2 words
Example 76
Claim 126
Dependent Claim
2 words
Example 76
Claim 127
Dependent Claim
2 words
Oil Suspension
Claim 128
Dependent Claim
2 words
Oil Suspension
Claim 129
Dependent Claim
32 words
The ingredients are combined and ground together in a sand mill to produce particles essentially all below 5 microns. The product can be used directly, extended with oils, or emulsified in water.
Claim 130
Dependent Claim
32 words
The ingredients are combined and ground together in a sand mill to produce particles essentially all below 5 microns. The product can be used directly, extended with oils, or emulsified in water.
Claim 131
Dependent Claim
2 words
Example 72
Claim 132
Dependent Claim
2 words
Example 72
Claim 133
Dependent Claim
2 words
Wettable Powder
Claim 134
Dependent Claim
2 words
Wettable Powder
Claim 135
Dependent Claim
35 words
The ingredients are thoroughly blended. After grinding in a hanger-mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged.
Claim 136
Dependent Claim
35 words
The ingredients are thoroughly blended. After grinding in a hanger-mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged.
Claim 137
Dependent Claim
2 words
Example 73
Claim 138
Dependent Claim
2 words
Example 73
Claim 139
Dependent Claim
4 words
Low Strength Granule -
Claim 140
Dependent Claim
4 words
Low Strength Granule -
Claim 141
Dependent Claim
45 words
The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged.
Claim 142
Dependent Claim
45 words
The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged.
Claim 143
Dependent Claim
43 words
The active ingredient is dissolved and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the material is warmed to evaporate the solvent. The material is allowed to cool and then packaged.
Claim 144
Dependent Claim
43 words
The active ingredient is dissolved and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the material is warmed to evaporate the solvent. The material is allowed to cool and then packaged.
Claim 145
Dependent Claim
2 words
Example 70
Claim 146
Dependent Claim
2 words
Example 70
Claim 147
Dependent Claim
1 words
Dust
Claim 148
Dependent Claim
1 words
Dust
Claim 149
Dependent Claim
33 words
The active ingredient is blended with attapulgite and then passed through a hammer mill to produce particles substantially all below 200 microns. The ground concentrate is then blended with powdered pyrophyllite until homogeneous.
Claim 150
Dependent Claim
33 words
The active ingredient is blended with attapulgite and then passed through a hammer mill to produce particles substantially all below 200 microns. The ground concentrate is then blended with powdered pyrophyllite until homogeneous.
Claim 151
Dependent Claim
2 words
Example 71
Claim 152
Dependent Claim
2 words
Example 71
Claim 153
Dependent Claim
2 words
Wettable Powder
Claim 154
Dependent Claim
2 words
Wettable Powder
Claim 155
Dependent Claim
27 words
The ingredients are blended, coarsely hammer-milled and then air-milled to produce particles of active essentially all below 10 microns in diameter. The product is reblended before packaging.
Claim 156
Dependent Claim
27 words
The ingredients are blended, coarsely hammer-milled and then air-milled to produce particles of active essentially all below 10 microns in diameter. The product is reblended before packaging.
Claim 157
Dependent Claim
34 words
may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled.
Claim 158
Dependent Claim
34 words
may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled.
Claim 159
Dependent Claim
2 words
Example 67
Claim 160
Dependent Claim
2 words
Example 67
Claim 161
Dependent Claim
2 words
Oil Suspension
Claim 162
Dependent Claim
2 words
Oil Suspension
Claim 163
Dependent Claim
40 words
The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water.
Claim 164
Dependent Claim
40 words
The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water.
Claim 165
Dependent Claim
2 words
Example 68
Claim 166
Dependent Claim
2 words
Example 68
Claim 167
Dependent Claim
1 words
Solution
Claim 168
Dependent Claim
1 words
Solution
Claim 169
Dependent Claim
21 words
The salt is added directly to the water with stirring to produce the solution, which may then be packaged for use.
Claim 170
Dependent Claim
21 words
The salt is added directly to the water with stirring to produce the solution, which may then be packaged for use.
Claim 171
Dependent Claim
2 words
Example 69
Claim 172
Dependent Claim
2 words
Example 69
Claim 173
Dependent Claim
3 words
Low Strength Granule
Claim 174
Dependent Claim
3 words
Low Strength Granule
Claim 175
Dependent Claim
2 words
Example b4
Claim 176
Dependent Claim
2 words
Example b4
Claim 177
Dependent Claim
2 words
Wettable Powder
Claim 178
Dependent Claim
2 words
Wettable Powder
Claim 179
Dependent Claim
17 words
The ingredients are blended, hammer-milled until all the solids are essentially under 50 microns and then reblended.
Claim 180
Dependent Claim
17 words
The ingredients are blended, hammer-milled until all the solids are essentially under 50 microns and then reblended.
Claim 181
Dependent Claim
2 words
Example 65
Claim 182
Dependent Claim
2 words
Example 65
Claim 183
Dependent Claim
1 words
Granule
Claim 184
Dependent Claim
1 words
Granule
Claim 185
Dependent Claim
26 words
A slurry of wettable powder containing ≈25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged.
Claim 186
Dependent Claim
26 words
A slurry of wettable powder containing ≈25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged.
Claim 187
Dependent Claim
2 words
Example 66
Claim 188
Dependent Claim
2 words
Example 66
Claim 189
Dependent Claim
2 words
Extruded Pellet
Claim 190
Dependent Claim
2 words
Extruded Pellet
Claim 191
Dependent Claim
43 words
The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets
Claim 192
Dependent Claim
43 words
The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets
Claim 193
Dependent Claim
2 words
Example 62
Claim 194
Dependent Claim
2 words
Example 62
Claim 195
Dependent Claim
1 words
Granule
Claim 196
Dependent Claim
1 words
Granule
Claim 197
Dependent Claim
104 words
The ingredients are blended and milled to pass through a 100 mesh screen. This material is then added to a fluid bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed'onto the fluidized material. The fluidization and spraying are continued .until granules of the desired size range are made. The spraying is stopped, but fluidization is continued, optionally with heat, until the water constant is reduced to the desired level, generally less than 1%. The material is then dischared, screened to the desired size range, generally 14-100 mesh (1410-149 microns), and packaged for use.
Claim 198
Dependent Claim
104 words
The ingredients are blended and milled to pass through a 100 mesh screen. This material is then added to a fluid bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed'onto the fluidized material. The fluidization and spraying are continued .until granules of the desired size range are made. The spraying is stopped, but fluidization is continued, optionally with heat, until the water constant is reduced to the desired level, generally less than 1%. The material is then dischared, screened to the desired size range, generally 14-100 mesh (1410-149 microns), and packaged for use.
Claim 199
Dependent Claim
2 words
Example 63
Claim 200
Dependent Claim
2 words
Example 63
Claim 201
Dependent Claim
2 words
High-Strength Concentrate
Claim 202
Dependent Claim
2 words
High-Strength Concentrate
Claim 203
Dependent Claim
31 words
The ingredients are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S.No. 50 screen (0.3 mm opening). The concentrate may be formulated further if necessary.
Claim 204
Dependent Claim
31 words
The ingredients are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S.No. 50 screen (0.3 mm opening). The concentrate may be formulated further if necessary.
Claim 205
Dependent Claim
2 words
Example 59
Claim 206
Dependent Claim
2 words
Example 59
Claim 207
Dependent Claim
2 words
Wettable Powder
Claim 208
Dependent Claim
2 words
Wettable Powder
Claim 209
Dependent Claim
27 words
The ingredients are blended, coarsely hammer-milled and then air-milled to produce particles of active essentially all below 10 microns in diameter. The product is reblended before packaging.
Claim 210
Dependent Claim
27 words
The ingredients are blended, coarsely hammer-milled and then air-milled to produce particles of active essentially all below 10 microns in diameter. The product is reblended before packaging.
Claim 211
Dependent Claim
2 words
Example 60
Claim 212
Dependent Claim
2 words
Example 60
Claim 213
Dependent Claim
1 words
Granule
Claim 214
Dependent Claim
1 words
Granule
Claim 215
Dependent Claim
26 words
A slurry of wettable powder containing ~25% solids is sprayed on the surface of attapulgite granules in a double-cone blended. The granules are dried and packaged.
Claim 216
Dependent Claim
26 words
A slurry of wettable powder containing ~25% solids is sprayed on the surface of attapulgite granules in a double-cone blended. The granules are dried and packaged.
Claim 217
Dependent Claim
2 words
Example 61
Claim 218
Dependent Claim
2 words
Example 61
Claim 219
Dependent Claim
2 words
Aqueous Suspension
Claim 220
Dependent Claim
2 words
Aqueous Suspension
Claim 221
Dependent Claim
21 words
The ingredients are blended and ground together in a sand mill to produce particles essentially of under 5 microns in size.
Claim 222
Dependent Claim
21 words
The ingredients are blended and ground together in a sand mill to produce particles essentially of under 5 microns in size.
Claim 223
Dependent Claim
1 words
N-[(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(methylthiomethyl)benzenesulfonamide;
Claim 224
Dependent Claim
1 words
N-[(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(methylthiomethyl)benzenesulfonamide;
Claim 225
Dependent Claim
1 words
N-[(4,6-Dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-(methylthiomethyl)benzenesulfonamide;
Claim 226
Dependent Claim
1 words
N-[(4,6-Dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-(methylthiomethyl)benzenesulfonamide;
Claim 227
Dependent Claim
1 words
N-[(4,6-Dimethylpyrimidin-2-yl)aminocarbonyl]-2-(methylsulfinylmethyl)benzenesulfonamide;
Claim 228
Dependent Claim
1 words
N-[(4,6-Dimethylpyrimidin-2-yl)aminocarbonyl]-2-(methylsulfinylmethyl)benzenesulfonamide;
Claim 229
Dependent Claim
1 words
N-[(4-Methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-(methylsulfonylmethyl)benzenesulfonamide;
Claim 230
Dependent Claim
1 words
N-[(4-Methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-(methylsulfonylmethyl)benzenesulfonamide;
Claim 231
Dependent Claim
1 words
N-[(4-Hethoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-(methylsulfinylmethyl)benzenesulfonamide;
Claim 232
Dependent Claim
1 words
N-[(4-Hethoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-(methylsulfinylmethyl)benzenesulfonamide;
Claim 233
Dependent Claim
1 words
N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(methylsulfonylmethyl)benzenesulfonamide;
Claim 234
Dependent Claim
1 words
N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(methylsulfonylmethyl)benzenesulfonamide;
Claim 235
Dependent Claim
1 words
N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(nethylzulfinylnethyl)benzenesulfonamide;
Claim 236
Dependent Claim
1 words
N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(nethylzulfinylnethyl)benzenesulfonamide;
Claim 237
Dependent Claim
1 words
N-[(4,6-Dimethylpyrinidin-2-yl)aminocarbonyl]-2-(methylsulfonylmethyl)benzenesulfonamide;
Claim 238
Dependent Claim
1 words
N-[(4,6-Dimethylpyrinidin-2-yl)aminocarbonyl]-2-(methylsulfonylmethyl)benzenesulfonamide;
Claim 239
Dependent Claim
1 words
N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(butoxymethyl)benzenesulfonamide;
Claim 240
Dependent Claim
1 words
N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(butoxymethyl)benzenesulfonamide;
Claim 241
Dependent Claim
1 words
N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(ethoxymethyl)benezenesulfonamide;
Claim 242
Dependent Claim
1 words
N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(ethoxymethyl)benezenesulfonamide;
Claim 243
Dependent Claim
1 words
N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl)-2-(1-methylpropylaxymethyl)benezenesulfonamide;
Claim 244
Dependent Claim
1 words
N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl)-2-(1-methylpropylaxymethyl)benezenesulfonamide;
Claim 245
Dependent Claim
2 words
2-((Dimethylamino)sulfonylmethyl]-N-((4,6-dimethyl- pyrimidin-2-yl)aminocarbonyl]bensenesulfonamide;
Claim 246
Dependent Claim
2 words
2-((Dimethylamino)sulfonylmethyl]-N-((4,6-dimethyl- pyrimidin-2-yl)aminocarbonyl]bensenesulfonamide;
Claim 247
Dependent Claim
4 words
2-[(Dimethylamino)sulfonylmethyl3-N-[(4,5-dimethoxy- pyrimidin-2-yl) aminocarbonyl] benzenesulfonamide;
Claim 248
Dependent Claim
4 words
2-[(Dimethylamino)sulfonylmethyl3-N-[(4,5-dimethoxy- pyrimidin-2-yl) aminocarbonyl] benzenesulfonamide;
Claim 249
Dependent Claim
4 words
2- [(Dimethylamino) sulfonylmethyl]-N-[ [(4-methoxy-6-methylpyrirnidin-2-yl)aminocarbonyl]benzenesulfonamide;
Claim 250
Dependent Claim
4 words
2- [(Dimethylamino) sulfonylmethyl]-N-[ [(4-methoxy-6-methylpyrirnidin-2-yl)aminocarbonyl]benzenesulfonamide;
Claim 251
Dependent Claim
1 words
2-[(Dimethylamino)sulfonylmethyl]-N-[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide;
Claim 252
Dependent Claim
1 words
2-[(Dimethylamino)sulfonylmethyl]-N-[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide;
Claim 253
Dependent Claim
1 words
2-[(Dimethylamino)sulfonylmethyl]-N-[(4,5-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide;
Claim 254
Dependent Claim
1 words
2-[(Dimethylamino)sulfonylmethyl]-N-[(4,5-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide;
Claim 255
Dependent Claim
2 words
2-[(Dimethylamino)sulfonylmethyl]-N-((4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl] benzenesulfonamide;
Claim 256
Dependent Claim
2 words
2-[(Dimethylamino)sulfonylmethyl]-N-((4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl] benzenesulfonamide;
Claim 257
Dependent Claim
3 words
N-[(4,6-Dimethoxypyrimidin-2-yl) aminocarbonyl] -2-(hydroxymethyl)benzenesulfonamide
Claim 258
Dependent Claim
3 words
N-[(4,6-Dimethoxypyrimidin-2-yl) aminocarbonyl] -2-(hydroxymethyl)benzenesulfonamide
Claim 259
Dependent Claim
2 words
N-[(4,6-Dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-(hydroxymethyl) benzenesulfonamide;
Claim 260
Dependent Claim
2 words
N-[(4,6-Dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-(hydroxymethyl) benzenesulfonamide;
Claim 261
Dependent Claim
1 words
N-[(4,6-Dimethylpyrimidin-2-yl)aminocarbonyl]-2-(hydroxymethyl)benzenesulfonamide;
Claim 262
Dependent Claim
1 words
N-[(4,6-Dimethylpyrimidin-2-yl)aminocarbonyl]-2-(hydroxymethyl)benzenesulfonamide;
Claim 263
Dependent Claim
1 words
N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-(hydroxymethyl)benzenesulfonamide;
Claim 264
Dependent Claim
1 words
N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-(hydroxymethyl)benzenesulfonamide;
Claim 265
Dependent Claim
2 words
N-[(4,6-Dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(hydroxymethyl)benzenesulfonamide; and
Claim 266
Dependent Claim
2 words
N-[(4,6-Dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(hydroxymethyl)benzenesulfonamide; and
Claim 267
Dependent Claim
7 words
N-[(4-Methoxy-5-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(hydroxymethyl) benzenesulfonamide; and agriculturally suitable salts thereof.
Claim 268
Dependent Claim
7 words
N-[(4-Methoxy-5-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(hydroxymethyl) benzenesulfonamide; and agriculturally suitable salts thereof.
Claim 269
Dependent Claim
88 words
11 . A compound of claim 1 wherein R , R 1 and R2 are as- defined in claim 1, W is O, R 8 is H, A is where Q, X, Y and Z are as defined in claim 1 and Y 1 is H, CH 3 or OCH3; and L is CO 2 R 10 , CONR 3 R 4 or CN, where R 10 is C 1 -C 4 alkyl; and R 3 and R 4 are independently H or C 1 -C 4 alkyl.
Claim 270
Dependent Claim
62 words
A compound-of claim 1 wherein: R is as defined in claim 1; R 1 is H or CH 3 ; R 2 is H or CH 3 ; L is SO 2 NR 3 R 4 where R 3 and R 4 are as defined in claim 1; R 8 is H; W is O; and A is defined in claim 11.
Claim 271
Dependent Claim
80 words
A compound of claim 1 wherein: R is as defined in claim 1; R 1 is H or C 1 -C 4 alkyl; R 2 is H or CH 3 ; R 8 is H; L is S (O) n R 7 or OR 9 ; R 7 and n are as defined in claim 1; R 9 is C 1 -C 4 alkyl, C 3 -C 4 alkenyl; A is as defined in claim 11; and W is 0.
Claim 272
Dependent Claim
55 words
A compound of claim 1 wherein R is as defined in claim 1; R 1 and R 2 are independently H or CH 3 ; R 8 is H; L is OH, OC (O) R 11 , OC(O)NHR 12 or OC O)OR 13 ; W is 0; and A is as defined in claim 11.
Claim 273
Dependent Claim
64 words
A compound of claim 1 wherein: R, R 1 and R 2 are as defined in claim 1; L is Cl, Br, NR 3 R 4 , NR 3 R 4 R 4 ', N(R 4 )C(O)R 5 , N(R 4 )C(O)NH 6 or N(R 4 )C(O)R 7 ; R 8 is H; W is O; and A is as defined in claim 11.
Claim 274
Dependent Claim
133 words
A compound selected from wherein R, R 1 , and R2 are as previously defined in claim 1; Z is CH or N; n is 0 or 2; and L is as previously defined in claim 1, provided that: (1) L is not OH; (2) when R 3 is OCH 3 , then R 4 is CH 3 and that 10 cannot be H; (3) when R 1 is Cl, then L is C1 or Br and R 2 is H; ( 4 ) when L is NR 3 R 4 , NR 3 R 4 R 4 ', or SO 2 NR 3 R 4 , then R 3 or R 4 cannot be H; (5) the total number of carbon atoms of R 3 and R 4 is five or less.
Claim 275
Dependent Claim
120 words
A compound selected from wherein R, R 1 , R 2 , R 7 and R 9 are as previously defined in claim 1 n is 0 or 2; L is Cl, Br, CO 2 R 10 , SO 2 NR 3 R 4 , S(O) n R 7 or OR 9 , provided that: (1) when R 1 is Cl, then L is Cl or Br and R 2 is H ; (2) when L is SO 2 NR 3 R 4 , then R 3 and R 4 cannot be H; (3) when R3 is OCH 3 , then R 4 is CH 3 ; (4) R 10 cannot be H; and (5) n is 0 or 2.
Claim 276
Dependent Claim
47 words
A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a herbicidal composition and at least one of the following: Surfactant, solid or liquid diluent, characterised in that said herbicidal compound comprises a compound of any of claims 1 to 15.
Claim 277
Independent Claim
40 words
A method for controlling the growth of undesired vegetation by applying to the locus of such vegetation an effective amount of a herbicidal compound, characterised in that said herbicidal compound comprises a compound of any of claims 1 to 15.
Claim 278
Independent Claim
44 words
A method for regulating the growth of plants by applying to the locus of said plants an effective but substantially non-phytotoxic amount of a plant growth regulant, characterised in that said plant growth regulant comprises a compound of any of claims 1 to 15.
Claim 279
Dependent Claim
614 words
A process for preparing a compound of claim 1 which comprises: (a) reacting together wherein L is C1, Br, CO 2 R 10 , SO 2 NR 3 R 4 , S(O) n R 7 , OR 9 ; n is 0 or 2; R, R 1 , R 2 , R 3 , R 4 , R7, R 8 , R 9 , R 10 and A are as defined in claim 1 except that R3, R 4 and R 10 cannot be H; (b) oxidising a compound of claim 1 wherein n is . O or 1 to a compound wherein n is 1 or 2; (c) hydrolyzing a compound of claim 1 wherein R 10 is C 1 -C 4 alkyl to a compound wherein R 10 is H; (d) reacting a compound of claim 1 wherein L is CO 2 R 10 (where R 10 is C 1 -C 4 alkyl) with a dialkylaluminum-N-alkylamide derivative of general formula wherein R 3 and R 4 are as defined in claim 1 and Alk is an alkyl group, to obtain a compound of claim 1 wherein L is C(O)NR 3 R 4 ; (e) reacting an appropriately substituted sulfonamide of general formula with the methylcarbamate of the appropriate aminohetero- cycle of general formula wherein R, R 1 , R 2 , R 8 , L and A are groups as defined in claim 1 inert under the reaction conditions; (f) displacing one or both chlorine atoms in the heterocyclic moiety of a compound of general formula (wherein R, R 1 , R 2 and L are as defined in claim 1 and Z is N or CH), by alkoxy groups within the definitions of X and Y in claim 1; (g) reacting together compounds of general formulae wherein R, R 1 , R 2 , L and A are as defined in claim 1, to obtain a compound of claim 1 wherein W is S; (h) reacting a compound of claim 1 wherein L is OH with wherein R 11 is as defined in claim 1, to obtain a compound of claim 1 wherein L is OC(O)R 11 ; (i) reacting a compound of claim 1 wherein L is OH with an isocyanate of general formula wherein R 12 is as defined in claim 1, to obtain a compound of claim 1 wherein L is OC (O) NHR 12 ; (j) reacting a compound of claim 1 wherein L is OH with a chloroformate of general formula wherein R 13 is as defined in claim 1, to obtain a compound of claim 1 wherein L is OC(O)OR 13 ; (k) reducing a compound of general formula or an ester thereof to obtain a compound of claim 1 wherein R 1 and R 2 are H and R, R 8 and A are as defined in claim 1; (1) reducing a ketone of general formula wherein R, R 8 and A are as defined in claim 1, to obtain a compound of claim 1 wherein R 1 is H, R 2 is CH 3 and L is OH; or reacting said ketone with methyl lithium to obtain a compound of claim 1 wherein R 1 and R 2 are CH 3 and L is OH, the substituent groups containing no displaceable halogen, N0 2 or CN; or (m) reacting a compound of general formula wherein R, R 8 and A are as defined in claim 1, with the proviso that they contain no displaceable halogens, NO 2 or CN, with methyl lithium to obtain a compound of claim 1 wherein R 1 is H, R 2 is CH 3 and L is OH.
References Cited (Backward Citations)
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