EP0400013A1 - Herbizide alkanoylpyridinsulfonylharnstoffe - Google Patents

Herbizide alkanoylpyridinsulfonylharnstoffe

Info

Publication number
EP0400013A1
EP0400013A1 EP89900156A EP89900156A EP0400013A1 EP 0400013 A1 EP0400013 A1 EP 0400013A1 EP 89900156 A EP89900156 A EP 89900156A EP 89900156 A EP89900156 A EP 89900156A EP 0400013 A1 EP0400013 A1 EP 0400013A1
Authority
EP
European Patent Office
Prior art keywords
corn
cmpd
nutsedge
amino
crabgrass
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Withdrawn
Application number
EP89900156A
Other languages
English (en)
French (fr)
Inventor
Kofi Sam Amuti
Daniel Carl Leep
Barry Arthur Wexler
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of EP0400013A1 publication Critical patent/EP0400013A1/de
Withdrawn legal-status Critical Current

Links

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

Definitions

  • New compounds effective for controlling the growth of undesired vegetation are in constant demand. ⁇ n the most common situation, such compounds are sought to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth not only in such crops but also in plantation crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around railroad tracks, storage tanks and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.
  • sulfonylurea herbicides are an extremely potent class of herbicides discovered within the last few years which generally consist of a sulfonylurea bridge, -SO 2 NHCONH-, linking two aromatic or heteroaromatic rings.
  • X is methyl, methoxy or ethoxy
  • R b is the same as R a or NR c R d ;
  • E is CH or N.
  • Y is O or S
  • E is N or CH
  • U.S. 4,435,206 discloses herbicidal pyridine-2-sulfonylureas, wherein the pyridine ring may be substituted by CI, Br, F, C 1 -C4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, NO 2 or a carboxylic ester group, but does not disclose compounds of the invention.
  • R is H or CH 3 ;
  • R 1 is CH 3 , CH 2 CH 3 or (CH 2 ) 2 CH 3 ;
  • X is CH 3 , OCH 3 or CI;
  • the desired product is insoluble in the reaction solvent at ambient temperature and crystallizes from it in pure form. Products soluble in the reaction solvent are isolated by evaporation of the solvent.
  • Compounds of Formula I then may be purified by trituration of the evaporation residue with solvents such as 1-chlorobutane or ethyl ether and filtration, by recrystallization from mixtures of solvents such as 1,2-dichloroethane, 1-chlorobutane and heptane or by chromatography on silica gel.
  • solvents such as 1-chlorobutane or ethyl ether and filtration, by recrystallization from mixtures of solvents such as 1,2-dichloroethane, 1-chlorobutane and heptane or by chromatography on silica gel.
  • Sulfonyl isocyanates (II) are known in the art and are prepared from the corresponding sulfonamides (IV) by one of the following two general
  • 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.
  • 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. 50 screen and then packaged.
  • the ingredients are thoroughly blended. After grinding in a hammer-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.
  • PPG-1013 5-[2-chloro-4-(trifluoromethyl)- phenoxy]-2-nitroacetophenone oxime-O-acetic acid, methyl ester procyazme 2-[[4-chloro-6-(cyclopropylamino)-1,3,5- triazine-2-yl]amino]-2-methylpropanenitrile profluralin N-(cyclopropylmethyl)-2,6-dinitro-N- pro ⁇ yl-4-(trifluoromethyl)benzenamine prometon 6-methoxy-N,N'-bis(1-methylethyl)-1,3,5- triazine-2,4-diamine prometryn N,N'-bis(1-methylethyl)-6-(methylthio)- 1,3,5-triazine-2,4-diamine pronamide 3,5-dichloro-N-(1,1-dimethyl-2-propynyl)benzamide propachlor 2-chloro-N
  • the second pot was planted with green foxtail (Setaria viridis), cocklebur (Xanthium pensylvanicum), morningglory (Ipomoea hederacea), cotton (Gossypium hirsutum), johnsongrass (Sorghum halepense), barnyardgrass (Echinochloa crus-galli), corn (Zea mays), soybean (Glycine max), and giant foxtail (Setaria faberi).
  • green foxtail Setaria viridis
  • cocklebur Xanthium pensylvanicum
  • morningglory Ipomoea hederacea
  • cotton Gossypium hirsutum
  • johnsongrass Sorghum halepense
  • barnyardgrass Echinochloa crus-galli
  • corn Zea mays
  • soybean Glycine max
  • giant foxtail Setaria faberi
  • the third pot was planted with wheat (Triticum aestivum), barley (Hordeum vulgare), wild buckwheat (Polygonum convolvulus), downy brome (Bromus tectorum), sugarbeet (Beta vulgaris), wild oat (Avena fatua), common chickweed (Stellaria media), blackgrass (Alopecurus mvosuroides), and rape (Brassica napus).
  • the plants were grown for approximately fourteen days, then sprayed postemergence with the chemicals dissolved in a non-phytoxic solvent. Preemergence
  • Response ratings are based on a scale of 0 to 100 where 0 indicates no effect, and 100 indicates complete control. A dash (-) response means no test. Response ratings are contained in Table B.
  • GIANT FOXTAIL 100 100 100 100 100 100 100 100
  • CRABGRASS 100 100 90 60
  • NUTSEDGE 100 100 90 80
  • LAMBSQUARTER 100 100 90 80
  • JIMSONWEED 100 100 90 70
  • LAMBSQUARTER 100 100 100 90
  • JIMSONWEED 100 100 90 60
  • NUTSEDGE 100 100 60 20
  • LAMBSQUARTER 100 100 90 60
  • Postemergence plantings were grown in Sassafras sandy loam soil. Corn and soybeans were grown in separate 25-cm diameter containers. Sorghum and the seven grass weed species were grown in two 18-cm diameter containers, 4 species per container. The seven broadleaf weed species were also grown in two 18-cm diameter containers, 4 species in one container, 3 species in the second container.
  • One additional planting of corn in an 18-cm diameter container was made. The soil surface of this additional container of corn was covered with the absorbent, perlite, before spray treatment so that test chemicals would enter the plant only via the foliage. The plants were grown 10-21 days, dependent upon the species and then sprayed postemergence with the test chemicals dissolved in a nonphytotoxic solvent.
  • Preemergence Preemergence plantings were grown in fertilized Tama silt loam soil. These plantings are identical to those described in the postemergence section, with the exception of the corn planting having perlite covering the soil surface. These plantings were made the day of or the day before spraying the test chemicals dissolved in a nonphytotoxic solvent. Evaluation
  • PERLITE CORN 1 0 0 0 0 0 0 20 1 Denotes results using soil covered with perlite at time of treatment as noted in the test description.
  • GREEN FOXTAIL 85 100 100 100 100 100 100 100 100 100 100
  • GIANT FOXTAIL 85 100 100 100 100 100 100 100 100 100
  • BARNYARDGRASS 90 100 100 100 100 100 100 100 100 100 100 100 100
  • LAMBSQUARTER 85 100 100 100 100 100 100 100 100 100
  • MORNINGLORY 75 90 100 100 100 100
  • JOHNSONGRASS 75 100 100 100 100 100 100 100 100
  • LAMBSQUARTER 80 100 ⁇ oo 100 100
  • PIGWEED 90 100 100 100 100 100 100 100
  • BARNYARDGRASS 75 50 95 100 100 100 100 100
  • JOHNSONGRASS 80 95 100 100 100 100 100 100 100

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
EP89900156A 1987-11-20 1988-11-18 Herbizide alkanoylpyridinsulfonylharnstoffe Withdrawn EP0400013A1 (de)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US12348187A 1987-11-20 1987-11-20
US12348287A 1987-11-20 1987-11-20
US22693488A 1988-08-01 1988-08-01
US226934 1988-08-01
US123482 1993-09-16
US123481 1993-09-16

Publications (1)

Publication Number Publication Date
EP0400013A1 true EP0400013A1 (de) 1990-12-05

Family

ID=27382957

Family Applications (2)

Application Number Title Priority Date Filing Date
EP88310907A Withdrawn EP0317336A1 (de) 1987-11-20 1988-11-18 Herbizide Alkanoylpyridinsulfonylharnstoffe
EP89900156A Withdrawn EP0400013A1 (de) 1987-11-20 1988-11-18 Herbizide alkanoylpyridinsulfonylharnstoffe

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP88310907A Withdrawn EP0317336A1 (de) 1987-11-20 1988-11-18 Herbizide Alkanoylpyridinsulfonylharnstoffe

Country Status (5)

Country Link
EP (2) EP0317336A1 (de)
JP (1) JPH03501607A (de)
KR (1) KR890701019A (de)
AU (1) AU2809289A (de)
WO (1) WO1989004605A1 (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2059450A1 (en) * 1991-01-24 1992-07-25 Nobuyuki Sakashita Subsituted pyridinesulfonamide compound or its salt, process for preparing the same, and herbicide containing the same
DE59208670D1 (de) * 1991-04-11 1997-08-14 Hoechst Schering Agrevo Gmbh Verfahren zur Herstellung von 2-Pyridylsulfonylharnstoffen und Thiadiazolopyridine als Zwischenprodukte in diesem Verfahren

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ZM5186A1 (en) * 1985-07-03 1986-12-29 Coopers Animal Health Tick vaccine
JPS62111982A (ja) * 1985-11-12 1987-05-22 Ishihara Sangyo Kaisha Ltd 置換ピリジンスルホンアミド系化合物及びそれらを含有する除草剤
CA1309715C (en) * 1986-05-02 1992-11-03 Barry A. Wexler Herbicidal heterocyclic sulfonamides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO8904605A1 *

Also Published As

Publication number Publication date
EP0317336A1 (de) 1989-05-24
AU2809289A (en) 1989-06-14
JPH03501607A (ja) 1991-04-11
WO1989004605A1 (en) 1989-06-01
KR890701019A (ko) 1989-12-19

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Legal Events

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