WO1988009617A1 - 1-(chloro-4-fluoro-2-methoxyphenyl-5)-3-methyl-4-difluoromethyl-delta2-1,2,4-triazolin-5-one a titre d'agent herbicide - Google Patents

1-(chloro-4-fluoro-2-methoxyphenyl-5)-3-methyl-4-difluoromethyl-delta2-1,2,4-triazolin-5-one a titre d'agent herbicide Download PDF

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Publication number
WO1988009617A1
WO1988009617A1 PCT/US1987/001406 US8701406W WO8809617A1 WO 1988009617 A1 WO1988009617 A1 WO 1988009617A1 US 8701406 W US8701406 W US 8701406W WO 8809617 A1 WO8809617 A1 WO 8809617A1
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WO
WIPO (PCT)
Prior art keywords
chloro
herbicidal
compound
fluoro
methyl
Prior art date
Application number
PCT/US1987/001406
Other languages
English (en)
Inventor
Lester Lawrence Maravetz
George Theodoridis
Original Assignee
Fmc Corporation
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 Fmc Corporation filed Critical Fmc Corporation
Priority to PCT/US1987/001406 priority Critical patent/WO1988009617A1/fr
Publication of WO1988009617A1 publication Critical patent/WO1988009617A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12—Oxygen or sulfur atoms
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Definitions

  • the invention described in this application pertains to weed control in agriculture, horticulture, or other fields where there is a desire to control unwanted plant growth. More specifically, the present application describes the use of l-(4-chloro-2-fluoro-5- methoxyphenyl)-3-methyl-4-difluoromethyl- ⁇ 2 -l,2,4- triazolin-5-one as a herbicidal agent, herbicidal compositions containing this compound, a method for preparing the compound, and methods for preventing or destroying undesired plant growth by preemergence or post-emergence application of the herbicidal composi ⁇ tions to the locus where control is desired.
  • the present compounds may be used to effectively control a variety of both grassy and broadleaf plant species.
  • the present invention is particularly useful in agriculture, as the herbicidal compound described herein shows a selectivity favorable to cotton or other crops at application levels which inhibit the growth of or destroy a variety of weeds.
  • R is a radical selected from 2-propynyl, 1- methylethyl, l-methyl-2-propynyl, methoxymethyl, 2- propenyl, and l-methyl-2-methoxyethyl and herbicidal compositions containing these compounds are disclosed in EP-A-177553 (Application No. 85901703.0).
  • the compound which is used in this invention may be prepared as described in EP-A-177553.
  • a method of preparation exemplified herein is illustrated in the following chemical equations.
  • the active compound I is formulated into herbicidal compositions by admixture in herbicidally effective amounts with adjuvants and carriers normally employed in the art for facilitating the dispersion of active ingredients for the particular utility desired, recognizing the fact that the formula ⁇ tion and mode of application of a toxicant may affect the activity of the material in a given application.
  • the present herbicidal - ° compound may be formulated as granules of relatively " large * particle size,- as water-soluble or water-disper ⁇ i- ble granules, as powdery dusts, as wettable powders, as emulsifiable concentrates, as solutions, or as any of several other known types of formulations, depending on the desired mode of application.
  • These herbicidal compositions may be applied either as water-diluted sprays, or dusts, or granules in the areas in which suppression of vegetation is desired.
  • These formulations may contain as little as 0.1%, 0.2% or 0.5% to as much as 95% or more by weight of active ingredient.
  • Dusts are free flowing admixtures of the active ingredient with finely divided solids such as talc, natural clays, kieselguhr, flours such as walnut shell and cottonseed flours, and other organic and inorganic solids which act as dispersants and carriers for the toxicant; these finely divided solids have an average particle size of less than about 50 microns.
  • a typical dust formulation useful herein is one containing 1.0 part or less of the herbicidal compound and 99.0 parts of talc.
  • Wettable powders also useful formulations for both pre- and postemergence herbicides, are in the form of finely divided particles which disperse readily in water or other dispersant.
  • the wettable powder is ultimately applied to the soil either as a dry dust or as an emulsion in water or other liquid.
  • Typical carriers for wettable powders include Fuller's earth, kaolin clays, silicas, and other highly absorbent, readily wet inorganic diluents. Wettable powders normally are prepared to contain about 5-90% of active ingredient, depending on the absorbency of the carrier, and usually also contain a small amount of a wetting, dispersing or emulsifying agent to facilitate dispersion.
  • a useful wettable powder formulation contains 80.8 parts of the herbicidal compound, 17.9 parts of Palmetto clay, and 1.0 part of sodium lignosulfonate and 0.3 part of sulfonated aliphatic polyester as wetting agents.
  • Other wettable powder formulations are: Component: % by Wt. Active ingredient 40. ,00 Sodium ligninsulfonate 20. ,00 Attapulgite clay 40. ,00 Total 100. ,00
  • Active ingredient 90 .00 Dioctyl sodium sulfosuccinate 0. .10 Synthetic fine silica 9. .90 Total 100. .00
  • Active ingredient 20 .00 Sodium alkylnaphthalenesulfonate 4, .00 Sodium ligninsulfonate 4. .00 Low viscosity methyl cellulose 3. .00 Attapulgite clay 69. .00 Total 100, .00
  • muls * ifiable concentrates which are homogeneous liquid or paste compositions dispersible ' in water -or. other dispersant, .and may consist entirely of the herbicidal compound and a liquid or solid emulsify- ing agent, or may also contain a liquid carrier, such as xylene, heavy aromatic naphthas, isophorone, or other non-volatile organic solvent.
  • ECs ifiable concentrates
  • these concentrates are dispersed in water or other liquid carrier, and normally applied as a spray to the area to be treated.
  • the percentage by weight of the essential active ingredient may vary according to the manner in which the composition is to be applied, but in general comprises .0.5 to 95% of active ingredient by weight of the herbicidal composition.
  • an e ul ⁇ ifiable concentrate may have the following composition (in % by weight) :
  • the antimicrobial agent is sodium o-phenylphenate tetrahydrate sold under the trademark and designation "Dowacide A”.
  • the foam suppressant is a water dilutable silicone emulsion sold under the trademark and designa ⁇ tion "Dow Corning AF" .
  • Surfactant C is a non-ionic paste of a condensate of ethylene oxide with a hydro- phobic base formed by condensing propylene oxide with propylene glycol, sold under the trademark and designa ⁇ tion "Pluronic P-84.”
  • Surfactant D is an anionic liquid comprising the sodium salt of a complex organic phos- phate ester, sold under the trademark and designation "GAFAC LO-529.”
  • the thickener is a xanthan gum sold under the trademark and designation "Kelzan-M”.
  • the suspending agent is a colloidal magnesium aluminum silicate sold under the trademark and designation "Veegum.”
  • Active ingredient 53.01 Blend of alk lnaphthalenesulfonate and polyoxyethylene ethers 6.00
  • Flowable formulations are similar to ECs except that the active ingredient is suspended in a liquid carrier, generally water.
  • Flowables like ECs, may include a small amount of a surfactant, and contain active ingredient in the range of 0.5 to 95%, frequently from 10 to 50%, by weight of the composition.
  • flowables may be diluted in water or other liquid vehicle, and are normally applied as a spray to the area to be treated.
  • Propylene glycol 7 50 Acetylenic alcohols 2 . 50 Xanthan gum 0 . 80 Total 100 , . 00
  • Component % bv Wt . Active ingredient 45 . . 00 Water 48 . , 50 Purified smectite clay 2 . 00 Xanthan gum 0 . 50
  • Typical wetting, dispersing or emulsifying agents used in agricultural formulations include, but are not limited to, the alkyl and alkylaryl ⁇ ulfonates and sulfates and their sodium salts; alkylaryl polyether alcohols; sulfated higher alcohols; polyethylene oxides; ⁇ ulfonated animal and vegetable oils; sulfonated petroleum oils, fatty acids esters of polyhydric alcohols and the ethylene oxide addition products of ⁇ uch e ⁇ ter ⁇ ; and the addition product of long-chain mercaptans and ethylene oxide.
  • the surface-active agent when used, normally comprises from 1 to 15% by weight of the composition.
  • compositions include simple solutions or suspensions of the active ingredient in a relatively non-volatile solvent such as water, corn oil, kerosene, propylene glycol, or other suitable solvents.
  • a relatively non-volatile solvent such as water, corn oil, kerosene, propylene glycol, or other suitable solvents.
  • Oil Suspension % bv Wt. Active ingredient 25.00
  • herbicidal applica- tions include simple solutions of the active ingredient in a solvent in which it is completely soluble at the desired concentration, such as acetone, alkylated naphthalenes, xylene, or other organic solvents.
  • a suitable solution may contain, for instance, some 65% of the active ingredient, together with a minor proportion (say 1 to 10%) of a surfactant.
  • Granular formulations wherein the toxicant is carried on relatively coarse particles, are of parti- cular utility for aerial distribution or for penetration of cover crop canopy.
  • Pressuriz-ed sprays typically aerosols wherein the active .ingredient is di ⁇ per ⁇ ed in finely divided form as a result of vaporization of a low ; boiling ' dispersant solvent carrier'., such a ⁇ the Freons,. may al ⁇ o be u ⁇ ed.
  • Water- ⁇ oluble or water-dispersible granules are al ⁇ o useful formulations for herbicidal application of the present compounds. Such granular formulations are free-flowing, non-dusty, and readily water-soluble or water-miscible.
  • the soluble or dispersible granular 5 formulations described in U.S. patent No. 3,920,442 are useful herein with the present herbicidal compounds.
  • the water- dispersible/soluble granular formulations In use by the farmer on the field, the water- dispersible/soluble granular formulations, emulsifiable concentrates, flowable concentrates, solutions, etc.,
  • 10 may be diluted with water to give a concentration of active ingredient in the range of say 0.1% or 0.2% to 1.5% or 2%.
  • the active herbicidal compound of this invention may be formulated and/or applied with insecticides,
  • an effective amount and concentration of the active compound is of course employed; the amount may be as low as 50 g/ha or lower, usually about 50 to 1000 g/ha, preferably 100 to 500 g/ha.
  • the active herbicidal compound of this invention may be used in combination with other herbicides, e.g. it may be mixed with, say, an equal or larger amount of a known herbicide such as chloroacetanilide herbicides such as 2-chloro-N-(2,6-diethylphenyl)-N-(methoxy-
  • a known herbicide such as chloroacetanilide herbicides such as 2-chloro-N-(2,6-diethylphenyl)-N-(methoxy-
  • triazine herbicides such as 6-chloro-N-ethyl-N-(1-methy1ethyl)-1,3,5- triazine-2,4-diamine (atrazine) , and 2-[4-chloro-6-
  • aryl urea herbicides such as N'-(3,4- dichlorophenyl)-N,N-dimethylurea (diuron) and N,N- dimethyl-N'-[3-(trifluoromethyl)phenyl]urea (fluo- meturon) ; and other heterocyclic nitrogen herbicides such as 2-[(2-chlorophenyl)methyl]-4,4-dimethyl-3- isoxazolidone.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Utilisation du composé de formule (I) à titre d'agent herbicide et compositions herbicides contenant ce composé. Ce composé est particulièrement efficace dans le cadre d'une utilisation avant émergence dans les champs de coton.
PCT/US1987/001406 1987-06-12 1987-06-12 1-(chloro-4-fluoro-2-methoxyphenyl-5)-3-methyl-4-difluoromethyl-delta2-1,2,4-triazolin-5-one a titre d'agent herbicide WO1988009617A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/US1987/001406 WO1988009617A1 (fr) 1987-06-12 1987-06-12 1-(chloro-4-fluoro-2-methoxyphenyl-5)-3-methyl-4-difluoromethyl-delta2-1,2,4-triazolin-5-one a titre d'agent herbicide

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US1987/001406 WO1988009617A1 (fr) 1987-06-12 1987-06-12 1-(chloro-4-fluoro-2-methoxyphenyl-5)-3-methyl-4-difluoromethyl-delta2-1,2,4-triazolin-5-one a titre d'agent herbicide

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Publication Number Publication Date
WO1988009617A1 true WO1988009617A1 (fr) 1988-12-15

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997024337A1 (fr) * 1995-12-29 1997-07-10 Fmc Corporation Chloration selective d'un 1-(2-fluoro-phenyl)-1,2,4-triazole
US6297192B1 (en) 1998-01-24 2001-10-02 Bayer Aktiengesellschaft Selective herbicides based on N-aryl-triazoline(thi)ons and N-arlysulfonylamino(thio)carbonyl-triazoline(thi)ons
US6841517B1 (en) 1999-09-30 2005-01-11 Bayer Aktiengesellschaft Selective herbicides on basis of N-aryl-triazoline(thi)ones

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4213773A (en) * 1977-11-17 1980-07-22 E. I. Du Pont De Nemours And Company Herbicidal substituted bicyclic triazoles
US4318731A (en) * 1979-08-25 1982-03-09 Nihon Nohyaku Co., Ltd. Δ2 -1,2,4-triazolin-5-one derivatives and herbicidal usage thereof
JPS57181069A (en) * 1981-04-30 1982-11-08 Nippon Nohyaku Co Ltd Delta2-1,2,4-triazolin-5-one and its preparation and use
US4398943A (en) * 1980-12-25 1983-08-16 Nikon Nohyaku Co., Ltd. Triazolinone derivative and herbicidal use thereof
US4404019A (en) * 1980-12-24 1983-09-13 Sumitomo Chemical Company, Limited 3-Chloro-1-phenyl-1,2,4-triazolin-5-ones and their use as herbicides
JPS58157771A (ja) * 1982-03-11 1983-09-19 Nippon Nohyaku Co Ltd △２−１，２，４−トリアゾリン−５−オン誘導体及びその製法並びにその用途
GB2162511A (en) * 1984-05-31 1986-02-05 Nihon Nohyaku Co Ltd Herbicidal triazolinone derivatives

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4213773A (en) * 1977-11-17 1980-07-22 E. I. Du Pont De Nemours And Company Herbicidal substituted bicyclic triazoles
US4318731A (en) * 1979-08-25 1982-03-09 Nihon Nohyaku Co., Ltd. Δ2 -1,2,4-triazolin-5-one derivatives and herbicidal usage thereof
US4404019A (en) * 1980-12-24 1983-09-13 Sumitomo Chemical Company, Limited 3-Chloro-1-phenyl-1,2,4-triazolin-5-ones and their use as herbicides
US4398943A (en) * 1980-12-25 1983-08-16 Nikon Nohyaku Co., Ltd. Triazolinone derivative and herbicidal use thereof
JPS57181069A (en) * 1981-04-30 1982-11-08 Nippon Nohyaku Co Ltd Delta2-1,2,4-triazolin-5-one and its preparation and use
JPS58157771A (ja) * 1982-03-11 1983-09-19 Nippon Nohyaku Co Ltd △２−１，２，４−トリアゾリン−５−オン誘導体及びその製法並びにその用途
GB2162511A (en) * 1984-05-31 1986-02-05 Nihon Nohyaku Co Ltd Herbicidal triazolinone derivatives

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, Volume 100, No. 25, issued 18 June 1984, Nihon Nohyaku, "delta 2-1,2,4-Triazoline-5-One, Derivatives", Abstract No. 209881r, page 604. *
CHEMICAL ABSTRACTS, Volume 95, No 15 issued 12 October 1981, NIHON NOHYAKU, "Herbicidal delta 2-1,2,4-Triazoline-5-Ones", Abstract No. 132895s, page 676. *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997024337A1 (fr) * 1995-12-29 1997-07-10 Fmc Corporation Chloration selective d'un 1-(2-fluoro-phenyl)-1,2,4-triazole
CN1067383C (zh) * 1995-12-29 2001-06-20 Fmc有限公司 1－(2－氟苯基)－1,2,4－三唑的选择性氯化方法
US6297192B1 (en) 1998-01-24 2001-10-02 Bayer Aktiengesellschaft Selective herbicides based on N-aryl-triazoline(thi)ons and N-arlysulfonylamino(thio)carbonyl-triazoline(thi)ons
US6841517B1 (en) 1999-09-30 2005-01-11 Bayer Aktiengesellschaft Selective herbicides on basis of N-aryl-triazoline(thi)ones

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