WO1989005296A1 - Sulfonamides herbicides - Google Patents

Sulfonamides herbicides Download PDF

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Publication number
WO1989005296A1
WO1989005296A1 PCT/US1987/003110 US8703110W WO8905296A1 WO 1989005296 A1 WO1989005296 A1 WO 1989005296A1 US 8703110 W US8703110 W US 8703110W WO 8905296 A1 WO8905296 A1 WO 8905296A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
och
compound
growth
effective amount
Prior art date
Application number
PCT/US1987/003110
Other languages
English (en)
Inventor
Stephen Kenneth Gee
Original Assignee
E.I. Du Pont De Nemours And Company
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 E.I. Du Pont De Nemours And Company filed Critical E.I. Du Pont De Nemours And Company
Priority to EP87310713A priority Critical patent/EP0318620A1/fr
Priority to EP19880900190 priority patent/EP0394224A1/fr
Priority to AU10454/88A priority patent/AU1045488A/en
Priority to PCT/US1987/003110 priority patent/WO1989005296A1/fr
Publication of WO1989005296A1 publication Critical patent/WO1989005296A1/fr

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

  • R is H, F, Cl, Br, NO 2 , CF 3 , C 1 -C 3 alkyl or C 1 -C 3 alkoxy;
  • R 1 and R 2 independently include H, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or C 1 - 4 alkylthio which are optionally substituted by halogen. NO 2 ,
  • R 8 is C 1 -C 4 alkyl , C 2 -C 4 alkenyl or benzyl.
  • G is O, S. SO or SO 2 ; m is 0 or 1: n is 0, 1 or 2;
  • R 1 includes H, C 1 to C 3 alkyl. C 1 to C 3 haloalkyl and C 1 -C 2 alkyl substituted by C 1 -C 2 alkoxy. C 1 -C 2 haloalkoxy, C 1 -C 2 alkylthio, C 1 -C 2 haloalkylthio, C 1 -C 2 haloalkylthio or CN.
  • R 1 includes halogen. C 1 -C 4 alkyl, C 1 -C 4 alkoxy, CO 2 R 3 , CONR 4 R 5 , SO 2 NR 4 R 5 and certain heterocyclic aromatic moieties; R 2 includes a variety of substituted methyl moieties; and A is one of seven heteroaromatic radicals.
  • R 2 includes H, halogen. C 1 -C 5 alkyl and C 1 -C 4 haloalkyl.
  • EP-A-102,480 discloses herbicidal compounds of the formula
  • J is NHR 2 , NR 3 R 4 or
  • Re is H. C 1 -C 4 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl. CH 2 CH 2 Cl, CH 2 CH 2 F, C 1 -C 2 alkyl substituted with OCH 3 or SCH 3 or C 3 -C 6 cycloalkyl;
  • R 16 is H, C 1 -C 2 alkyl or F
  • R 18 is C 1 -C 2 alkyl
  • X is H, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkylthio, C 1 -C 4 alkylthio, halogen.
  • C 2 -C 5 alkoxyalkyl is H, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkylthio, halogen.
  • Y 3 is H or CH 3 ;
  • Y 4 is CH 3 , OCH 3 , OC 2 H 5 or Cl; and their agriculturally suitable salts; provided that
  • Alkoxy denotes methoxy, ethoxy. ri-propoxy, isopropoxy and the different butoxy isomers.
  • Alkenyl denotes straight chain or branched alkenes, e.g., vinyl. 1-propenyl, 2-propenyl. 3-propenyl and the different butenyl isomers.
  • halogen either alone or in compound words such as "haloalkyl”. denotes fluorine, chlorine. bromine or iodine. Further, when used in compound words such as “haloalkyl” said alkyl may be mono- halogenated or fully substituted with halogen atoms. which may be the same or different. Examples of haloalkyl include CH 2 CH 2 F, CF 2 CF 3 and CH 2 CHFCl.
  • W is O.
  • OCH 2 CF 3 OCH 2 CF 3 ; and Y is CH 3 .
  • Example 10 3-Bromomethyl-6-[((4,6-dimethoxypyrimidin-2-yl)-aminocarbonyl)aminosulfonynbenzoic acid, ethyl ester
  • phenyl ester in 5.0ml of dry acetonitrile was added 0.15ml of DBU. After stirring at room temperature for three hours, the reaction mixture was diluted with 5.0 ml of water and then acidified with IN hydrochloric acid to pH3. The solids were collected by vacuum filtration and washed with n-butylchloride to yield 0.38g of a white solid; m.p. 195-197°C;
  • the invention is further exemplified, but not limited to the compounds in Tables I-VII.
  • the com- pounds depicted in these tables may be prepared by methods described in Examples 1-10, or by modifications thereof apparent to those skilled in the art.
  • Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions. emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation.
  • the formulations broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid inert diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:
  • Example 18 Granule wettable powder of Example 17 15% gypsum 69% potassium sulfate 16%
  • the second pot was planted with green foxtail (Setaria viridis), cocklebur (Xantium pensylvanicum), morningglory (Ipomoea hederacea), cotton (Gossypium tiirsutum), johnsongrass (Sorghum halepense), barnyardgrass (Echinochloa crusgalli). corn (Zea mays), soybean (Qlycine max) and giant foxtail (Setaria faberi).
  • the third pot was planted with wheat (Triticum aestivum). barley (Hordeum vulgare).
  • Three round pans (25 cm diameter by 12.5 cm deep) were filled with Sassafras sandy loam soil.
  • One pan was planted with nut ⁇ edge tubers, crabgrass, sicklepod, jimsonweed, velvetleaf, lambsquarters, rice and teaweed.
  • the second pot was planted with green foxtail, cocklebur. morningglory, cotton, johnsongrass, barnyardgrass, corn, soybean and giant foxtail.
  • the third pot was planted with wheat, barley, wild buck-wheat, cheatgrass. sugarbeet, wild oat, viola, blackgrass and rape.
  • the three pans were sprayed preemer gence with the chemicals dissolved in a non-phytotoxic solvent.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (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)

Abstract

Les composés sont de formule (I), dans laquelle E représente CH2 ou une liaison simple; W représente O ou S; R représente H ou CH3; RX représente H, F, Cl, CH3, OCH3, N(CH3)2 ou OCHF2; R1 et R2 sont choisis dans divers groupes organiques, et A est choisi dans divers groupes hétérocycliques. Lesdits composés sont utiles en tant qu'herbicides et régulateurs de croissance de plantes.
PCT/US1987/003110 1987-12-04 1987-12-04 Sulfonamides herbicides WO1989005296A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP87310713A EP0318620A1 (fr) 1987-12-04 1987-12-04 Sulfonamides herbicides
EP19880900190 EP0394224A1 (fr) 1987-12-04 1987-12-04 Sulfonamides herbicides
AU10454/88A AU1045488A (en) 1987-12-04 1987-12-04 Herbicidal sulfonamides
PCT/US1987/003110 WO1989005296A1 (fr) 1987-12-04 1987-12-04 Sulfonamides herbicides

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US1987/003110 WO1989005296A1 (fr) 1987-12-04 1987-12-04 Sulfonamides herbicides

Publications (1)

Publication Number Publication Date
WO1989005296A1 true WO1989005296A1 (fr) 1989-06-15

Family

ID=22202683

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1987/003110 WO1989005296A1 (fr) 1987-12-04 1987-12-04 Sulfonamides herbicides

Country Status (3)

Country Link
EP (1) EP0394224A1 (fr)
AU (1) AU1045488A (fr)
WO (1) WO1989005296A1 (fr)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4302241A (en) * 1979-07-02 1981-11-24 E. I. Du Pont De Nemours And Company Agricultural sulfonamides
EP0177163A2 (fr) * 1984-08-27 1986-04-09 E.I. Du Pont De Nemours And Company Acétals et cétals herbicides
EP0187489A1 (fr) * 1984-12-11 1986-07-16 E.I. Du Pont De Nemours And Company Sulfonamides à activité herbicide
EP0205348A2 (fr) * 1985-06-12 1986-12-17 E.I. Du Pont De Nemours And Company Sulfonamides comme herbicides
EP0235449A1 (fr) * 1985-11-22 1987-09-09 E.I. Du Pont De Nemours And Company Sulfonamides herbicides

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4302241A (en) * 1979-07-02 1981-11-24 E. I. Du Pont De Nemours And Company Agricultural sulfonamides
EP0177163A2 (fr) * 1984-08-27 1986-04-09 E.I. Du Pont De Nemours And Company Acétals et cétals herbicides
EP0187489A1 (fr) * 1984-12-11 1986-07-16 E.I. Du Pont De Nemours And Company Sulfonamides à activité herbicide
EP0205348A2 (fr) * 1985-06-12 1986-12-17 E.I. Du Pont De Nemours And Company Sulfonamides comme herbicides
EP0235449A1 (fr) * 1985-11-22 1987-09-09 E.I. Du Pont De Nemours And Company Sulfonamides herbicides

Also Published As

Publication number Publication date
AU1045488A (en) 1989-07-05
EP0394224A1 (fr) 1990-10-31

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