EP0523067A1 - Sulfonamides herbicides selectifs - Google Patents
Sulfonamides herbicides selectifsInfo
- Publication number
- EP0523067A1 EP0523067A1 EP19910905178 EP91905178A EP0523067A1 EP 0523067 A1 EP0523067 A1 EP 0523067A1 EP 19910905178 EP19910905178 EP 19910905178 EP 91905178 A EP91905178 A EP 91905178A EP 0523067 A1 EP0523067 A1 EP 0523067A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- amino
- methyl
- compound
- sulfonyl
- benzoate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 229940124530 sulfonamide Drugs 0.000 title abstract description 7
- 150000003456 sulfonamides Chemical class 0.000 title abstract description 7
- 230000002363 herbicidal effect Effects 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 87
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 35
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 23
- 239000007787 solid Substances 0.000 claims description 23
- 240000008042 Zea mays Species 0.000 claims description 22
- 240000005979 Hordeum vulgare Species 0.000 claims description 18
- 235000007340 Hordeum vulgare Nutrition 0.000 claims description 18
- 239000003085 diluting agent Substances 0.000 claims description 16
- 241000209140 Triticum Species 0.000 claims description 15
- 235000021307 Triticum Nutrition 0.000 claims description 15
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 14
- 235000005822 corn Nutrition 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 230000012010 growth Effects 0.000 claims description 13
- 239000004094 surface-active agent Substances 0.000 claims description 13
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical group F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 5
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- IPWIBMCLQGAXRP-UHFFFAOYSA-N methyl 3-(difluoromethyl)-2-[(4-methoxypyrimidin-2-yl)carbamoylsulfamoyl]benzoate Chemical compound COC(=O)C1=CC=CC(C(F)F)=C1S(=O)(=O)NC(=O)NC1=NC=CC(OC)=N1 IPWIBMCLQGAXRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical group [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- TYDDKSZYFJLJIT-UHFFFAOYSA-N methyl 3-(cyanomethyl)-2-[(4,6-dimethylpyrimidin-2-yl)carbamoylsulfamoyl]benzoate Chemical compound COC(=O)C1=CC=CC(CC#N)=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 TYDDKSZYFJLJIT-UHFFFAOYSA-N 0.000 claims description 4
- QWKDZNHVUSEGJT-UHFFFAOYSA-N methyl 3-(fluoromethyl)-2-[(4-methoxypyrimidin-2-yl)carbamoylsulfamoyl]benzoate Chemical compound COC(=O)C1=CC=CC(CF)=C1S(=O)(=O)NC(=O)NC1=NC=CC(OC)=N1 QWKDZNHVUSEGJT-UHFFFAOYSA-N 0.000 claims description 4
- ZAIDHYKXQDFAOB-UHFFFAOYSA-N ethyl 2-[(4-chloro-6-methoxypyrimidin-2-yl)carbamoylsulfamoyl]-3-(fluoromethyl)benzoate Chemical compound CCOC(=O)C1=CC=CC(CF)=C1S(=O)(=O)NC(=O)NC1=NC(Cl)=CC(OC)=N1 ZAIDHYKXQDFAOB-UHFFFAOYSA-N 0.000 claims description 3
- LMAFITGITCTXTG-UHFFFAOYSA-N methyl 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-3-(fluoromethyl)benzoate Chemical compound COC(=O)C1=CC=CC(CF)=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 LMAFITGITCTXTG-UHFFFAOYSA-N 0.000 claims description 3
- HKBZXGIFRTWSJF-UHFFFAOYSA-N methyl 2-[(4-chloro-6-methoxypyrimidin-2-yl)carbamoylsulfamoyl]-3-(cyanomethyl)benzoate Chemical compound COC(=O)C1=CC=CC(CC#N)=C1S(=O)(=O)NC(=O)NC1=NC(Cl)=CC(OC)=N1 HKBZXGIFRTWSJF-UHFFFAOYSA-N 0.000 claims description 3
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 2
- 241000196324 Embryophyta Species 0.000 abstract description 51
- 239000004009 herbicide Substances 0.000 abstract description 10
- 235000013339 cereals Nutrition 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- 239000000126 substance Substances 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 25
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
- -1 sulfonyl benzoates Chemical class 0.000 description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
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- 238000005481 NMR spectroscopy Methods 0.000 description 16
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- QYPPRTNMGCREIM-UHFFFAOYSA-N Monomethylarsonic acid Natural products C[As](O)(O)=O QYPPRTNMGCREIM-UHFFFAOYSA-N 0.000 description 13
- 239000002689 soil Substances 0.000 description 13
- 235000007320 Avena fatua Nutrition 0.000 description 12
- 241000209764 Avena fatua Species 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- 241001621841 Alopecurus myosuroides Species 0.000 description 10
- 235000010469 Glycine max Nutrition 0.000 description 10
- 244000068988 Glycine max Species 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 10
- 240000006995 Abutilon theophrasti Species 0.000 description 9
- 244000075634 Cyperus rotundus Species 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
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- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 8
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- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 8
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- 244000152970 Digitaria sanguinalis Species 0.000 description 6
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
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- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
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- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- FZMKKCQHDROFNI-UHFFFAOYSA-N sulfometuron Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 FZMKKCQHDROFNI-UHFFFAOYSA-N 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 229910002029 synthetic silica gel Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- NKEVUMSCVLJVFU-UHFFFAOYSA-N tetraethylazanium isocyanate Chemical compound [N-]=C=O.CC[N+](CC)(CC)CC NKEVUMSCVLJVFU-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- LOQQVLXUKHKNIA-UHFFFAOYSA-N thifensulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C2=C(SC=C2)C(O)=O)=N1 LOQQVLXUKHKNIA-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D521/00—Heterocyclic compounds containing unspecified hetero rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/58—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/59—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/41—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by carboxyl groups, other than cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/78—Halides of sulfonic acids
- C07C309/86—Halides of sulfonic acids having halosulfonyl groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/89—Halides of sulfonic acids having halosulfonyl groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing carboxyl groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
Definitions
- Y is H, Cl, CH 3 , C 2 H 5 , OCH 3 or OCF 2 H;
- Z 1 is Cl or NHSiR 3 R 4 R 5 ;
- R 3 is C 1 -C 4 alkyl
- Equation 4 t-butyldimethylsilyl amine
- Exchange may also be effected by passing an aqueous solution of a salt of a compound of Formula I (e.g., an alkali metal or quaternary amine salt) through a column packed with a cation exchange resin containing the cation to be exchanged for that of the original salt and the desired product is eluted from the column.
- a salt of a compound of Formula I e.g., an alkali metal or quaternary amine salt
- a cation exchange resin containing the cation to be exchanged for that of the original salt and the desired product is eluted from the column.
- Methyl 3-Formyl-2-nitrobenzoate Methyl 3-(dibromomethyl)-2-nitrobenzoate (62.6 g), silver nitrate (109 g), 1,2-dimethoxyethane (500 mL), and water (400 mL) were heated at reflux
- Rates of application for compounds of this invention are determined by a number of factors.
- Compounds of this invention may be used alone or in combination with other commercial herbicides, insecticides, or fungicides.
- the following list exemplifies some of the herbicides suitable for use in mixtures.
- a combination of compounds from this invention with one or more of the following herbicides may be particularly useful for weed control.
- Plant iresponse ratings are based on a scale of 0 to 10 where 0 is no effect and 10 is complete control.
- a dash (-) response means no test result.
- soybean (Glycine max), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Triticum aestiyum), wild buckwheat (Polygonum convolyulus), and wild oat (Ayena fatua) and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were also treated with
- cocklebur Xanthium pensylvanicum
- corn Zea mays
- soil surface exposed and soil surface covered with perlite crabgrass (Digitaria spp.), fall panicum (Panicum dichotomiflorum), giant foxtail (Setaria faberii), green foxtail (Setaria viridis), ivyleaf morningglory (Ipomoea hederacea), jimsonweed (Datura stramonium), johnsongrass (Sorghum
- Plant response ratings summarized in Table G, are based upon a 0 to 10 scale where 0 is no effect and 10 is complete control. A dash response (-) means no test result.
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plural Heterocyclic Compounds (AREA)
- Small-Scale Networks (AREA)
- Communication Control (AREA)
- Optical Communication System (AREA)
Abstract
Nouveaux sulfonamides et leur emploi en tant qu'herbicides sélectifs. Les composés de l'invention présentent une excellente maîtrise des mauvaises herbes sans constituer de danger pour les céréales.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US50318290A | 1990-04-02 | 1990-04-02 | |
US503182 | 1990-04-02 |
Publications (1)
Publication Number | Publication Date |
---|---|
EP0523067A1 true EP0523067A1 (fr) | 1993-01-20 |
Family
ID=24001052
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP19910905178 Withdrawn EP0523067A1 (fr) | 1990-04-02 | 1991-02-26 | Sulfonamides herbicides selectifs |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP0523067A1 (fr) |
JP (1) | JP2799246B2 (fr) |
BR (1) | BR9106301A (fr) |
CA (1) | CA2079589A1 (fr) |
WO (1) | WO1991015478A1 (fr) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0537585B1 (fr) * | 1991-10-15 | 1997-08-20 | E.I. Du Pont De Nemours And Company | Procédé pour la préparation de sulfonylurées |
DE10036002A1 (de) | 2000-07-25 | 2002-02-14 | Aventis Cropscience Gmbh | Herbizide Mittel |
KR20040039430A (ko) * | 2001-09-28 | 2004-05-10 | 이하라케미칼 고교가부시키가이샤 | (2-니트로페닐)아세토니트릴 유도체의 제조방법 및 그합성중간체 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4491467A (en) * | 1981-08-24 | 1985-01-01 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
US4537618A (en) * | 1982-05-26 | 1985-08-27 | Ciba Geigy Corporation | N-phenylsulfonyl-N'-pyrimidinylureas |
CA1255329A (fr) * | 1984-10-19 | 1989-06-06 | Mitsuru Tanemura | Derives d'acide benzoique |
AU3430089A (en) * | 1988-03-24 | 1989-10-16 | E.I. Du Pont De Nemours And Company | Fluoroalkoxy amino triazines for control of weeds in sugar beets |
-
1991
- 1991-02-26 BR BR919106301A patent/BR9106301A/pt unknown
- 1991-02-26 CA CA 2079589 patent/CA2079589A1/fr not_active Abandoned
- 1991-02-26 JP JP3505118A patent/JP2799246B2/ja not_active Expired - Fee Related
- 1991-02-26 EP EP19910905178 patent/EP0523067A1/fr not_active Withdrawn
- 1991-02-26 WO PCT/US1991/001075 patent/WO1991015478A1/fr not_active Application Discontinuation
Non-Patent Citations (1)
Title |
---|
See references of WO9115478A1 * |
Also Published As
Publication number | Publication date |
---|---|
JP2799246B2 (ja) | 1998-09-17 |
CA2079589A1 (fr) | 1991-10-03 |
JPH05505796A (ja) | 1993-08-26 |
BR9106301A (pt) | 1993-04-13 |
WO1991015478A1 (fr) | 1991-10-17 |
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