EP0177553A4 - 1-ARYLE--g(d)?2 -1,2,4-TRIAZOLINE-5-ONES HERBICIDES. - Google Patents

1-ARYLE--g(d)?2 -1,2,4-TRIAZOLINE-5-ONES HERBICIDES.

Info

Publication number
EP0177553A4
EP0177553A4 EP19850901703 EP85901703A EP0177553A4 EP 0177553 A4 EP0177553 A4 EP 0177553A4 EP 19850901703 EP19850901703 EP 19850901703 EP 85901703 A EP85901703 A EP 85901703A EP 0177553 A4 EP0177553 A4 EP 0177553A4
Authority
EP
European Patent Office
Prior art keywords
compound
methyl
chloro
triazolin
herbicidal
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Withdrawn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
EP19850901703
Other languages
German (de)
English (en)
Other versions
EP0177553A1 (fr
Inventor
Lester Lawrence Maravetz
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.)
FMC Corp
Original Assignee
FMC Corp
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 Corp filed Critical FMC Corp
Publication of EP0177553A1 publication Critical patent/EP0177553A1/fr
Publication of EP0177553A4 publication Critical patent/EP0177553A4/fr
Withdrawn legal-status Critical Current

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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 novel herbicidal 1-aryl- ⁇ 2 - 1,2,4-triazolin-5-ones, herbicidal compositions containing the new compounds, methods for preparing the compounds, and methods for preventing or destroying undesired plant growth by preemergence or post-emergence application of the herbicidal compositions 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 novel aryltriazolinones described herein show a selectivity favorable to cotton or other crops at application levels which inhibit the growth of or destroy a variety of weeds.
  • Various herbicidal 1-aryl- ⁇ 2 -1,2,4-triazolin-5-ones are known in the art.
  • U.S. Patent No. 4,318,731 and corresponding British Patent No. 2,056,971 disclose herbicidal aryltriazolinones of the formula
  • R 1 is alkyl
  • R 2 is hydrogen, alkyl, or alkenyl
  • X is hydroxy, alkyl, alkoxy, alkoxy- alkoxy, alkenyloxy, or alkyloxycarbonylalkyloxy.
  • British Patent No. 2,090,250 a continuation-in-part of the above British patent, adds to the above genus compounds wherein R 2 is alkynyl, halomethyl, or haloethyl, and X is alkoxy, alkenyloxy, alkynyloxy, alkoxyalkoxy, hydroxy, halomethyloxy, or haloethyloxy.
  • European Patent Application Publication No. 55,105 discloses a series of herbicidal aryltriazolinones of the formula
  • R is alkyl, alkenyl, or cycloalkyl
  • X is chlorine or bromine
  • Y is hydrogen or alkoxy.
  • Japanese Kokai 81-32,468 discloses herbicidal aryltriazolinones of the formula
  • R is hydrogen, alkyl, or 2-propenyl, and R 1 is methyl or alkoxy.
  • R n is hydrogen or represents 1 to 4 same or different radicals selected from halogen, nitro, cyano, optionally halo substituted alkyl, alkoxy, or alkylthio, and optionally substituted phenyl or phenoxy, and R 1 is alkyl, alkoxyalkyl, dialkoxyethyl, dialkylaminoethyl, or cycloalkyl.
  • U.S. Patent No. 4,315,767 discloses herbicidal bicyclic compounds of the following formula
  • V is hydrogen, halogen, methyl, or alkoxy
  • X is hydrogen, halogen, cyano, methyl, methoxy, or nitro
  • Y is hydrogen, halogen, or methyl
  • m and n are 0 to 4 (m plus n is 2 to 4)
  • Q is oxygen or sulfur
  • Z is oxygen, S(O) p , or NR 1 wherein p is 0-2 and R 1 is alkyl, provided that when m plus n is 2 or
  • Patent No. 4,213,773 and have the following structural formula
  • V is hydrogen, halogen, hydroxy, alkyl, or -OR 1 ;
  • R 1 is optionally substituted alkyl, cycloalkyl, cycloalkylalkyl, optionally substituted alkenyl, alkynyl, optionally substituted benzyl, alkylaminocarbonyl, (alkyl) (methyl or methoxy)aminocarbonyl, acyl, alkoxycarbonyl, or -CHR 7 R 8 wherein
  • R 7 is hydrogen or alkyl and R 8 is cyano, acetyl, hydroxycarbonyl, alkoxycarbonyl, hydroxymethyl, alkoxymethyl, alkylcarbonyloxyrmethyl, hydroxycarbonylethenyl, alkoxycarbonylethenyl, or a group
  • R 11 is hydrogen, alkyl, alkenyl, or alkoxy, and R 12 is hydrogen or alkyl;
  • X is halogen, cyano, methyl, methoxy, or nitro;
  • Y is hydrogen, halogen, or methyl;
  • Z is hydrogen or halogen;
  • n is 3-5;
  • m is 0-2; and
  • Q is oxygen or sulfur, with certain provisos.
  • a class of ⁇ 2 -1,2,4-triazolin-5-ones is disclosed as fungicides in U.S. 4,098,896.
  • the disclosed genus has the formula
  • R is alkyl, alkenyl, alkynyl, cycloalkyl, or optionally substituted phenyl or arylalkyl
  • R 1 is haloalkyl or haloalkenyl
  • R 2 is optionally substituted alkyl, alkenyl, or alkynyl, or optionally substituted aryl, arylalkyl, or alkylaryl.
  • the compounds of this invention are 1-[4-chloro- 2-fluoro-5-(substituted)oxyphenyl]-3-methy1-4-difluoromethyl- ⁇ 2 -1,2,4-triazolin-5-ones of the formula
  • R is alkyl, alkenyl, alkynyl, alkpxyalkyl, or alkyl S(O) n -alkyl wherein n is 0 to 2.
  • the present compounds are named in accordance with the numbering system shown in formula I, for the ring atoms of the heterocycle which is the same as the numbering system used in U.S. 4,318,731, supra, for similar compounds.
  • a preferred embodiment of this invention is 1-(4- chloro-2-fluoro-5-propargyloxyphenyl)-3-methyl-4- difluoromethyl- ⁇ 2 -1,2,4-triazolin-5-one, the compound of the formula
  • the present compounds which have a fluorine atom at the C-2 position of the phenyl ring, in general have herbicidal properties far superior to those of the corresponding compounds having a chlorine atom at C-2 of the phenyl ring, and are highly active at low application rates against a variety of grassy and broadleaf weed species in both preemergence and postemergence applications.
  • the compounds of this invention may be prepared by methods analogous to the methods described in the references above for similar compounds or by methods within the skill of the art.
  • the disclosures in the above references pertaining to methods of preparation are incorporated herein by reference.
  • a method of preparation exemplified herein is illustrated in the following chemical equations for the compound of formula I(a).
  • the propargyloxy group also known as 2-propynyloxy
  • 2-propynyloxy may be added at an earlier stage in the synthesis rather than in the last step: for example, at the outset by using 4-chloro-2-fluoro-5-propargyloxyaniline as the starting material in place of compound II (the corresponding 5-methoxy compound).
  • 4-Chloro-2-fluoro-5-methoxyaniline, compound II was prepared in five steps from commercially available 2-chloro-4-fluorophenol in a known manner (see E. Nagano et al. in European Patent Application
  • reaction mixture was cooled to ambient temperature and extracted with aqueous 10% sodium hydroxide.
  • aqueous layer was separated and neutralized with gaseous carbon dioxide, and a solid was collected by filtration.
  • the solid was air-dried to give 11.0 g of 1-(4-chloro-2-fluoro-5-methoxyphenyl)-3-methyl- ⁇ 2 - 1,2,4-triazolin-5-one; mp 193-195°C.
  • This compound was prepared in a manner analogous to Example 2 using 0.50 g (0.0017 mole) of
  • This compound was prepared in the manner of
  • Example 2 using 0.75 g (0.0026 mole) of 1-(4-chloro-2-fluoro-5-hydroxyphenyl)-3-methyl-4-difluoromethyl- ⁇ 2 -1,2,4-triazolin-5-one, 0.21 g (0.026 mole) of chloromethyl methyl ether, and 0.35 g (0.0026 mole) of potassium carbonate in 60 mL of acetone.
  • Giant Foxtail (Giantfox) Setaria faberi Herrm.
  • Green Foxtail (Greenfox) Setaria viridis Ivyleaf Morningglory (Ivyglory) Ipomoea hederacea (L.) or Ipomoea lacumosa
  • Seeds or tubers of the plant test species were planted in furrows in steam sterilized sandy loam soil contained in disposable fiber flats.
  • the flats had been filled to a depth of about 6.5 cm with the soil.
  • a topping soil of equal portions of sand and sandy loam soil was placed uniformly on top pf each flat to a depth of approximately 0.5 cm.
  • the flats for the preemergence tests were watered, then drenched with the appropriate amount of a solution of the test compound in a mixture of acetone and water containing a small amount (up to 0.5% v/v) of sorbitan monolaurate emulsifier/solubilizer.
  • concentration of the test compound in solution was varied to give a range of application rates, generally 8.0 kg/ha and submultiples thereof.
  • the flats were placed in a greenhouse and watered regularly at the soil surface for 21 days at which time phytotoxicity data were recorded.
  • Compound I(a) is the compound of Example 2, 1-(4-chloro- 2-fluoro-5-propargyloxyphenyl)-3-methyl-4-difluoromethyl- ⁇ 2 -1,2,4-triazplin-5-one.
  • Compound I(a) is the compound of Example 2, 1-(4-chloro- 2-fluoro-5-propargyloxyphenyl)-3-methyl-4-difluororaethyl- ⁇ 2 -1,2,4-triazolin-5-one.
  • Rate of Applications (kg/ha) .5000 .2500 .1250 .0625 .0313 .0156
  • Compound A is 1-(2,4-dichloro-5-propargyloxyphenyl)-3- methyl-4-difluoromethyl- ⁇ 2 -1,2,4-triazolin-5-one.
  • BE % kill + X(100 - % kill) wherein X is a number assigned to the vigor rating according to the following schedule: vigor X
  • Tables 3 and 4 below show BE values calculated from the data in Tables 1 and 2 above for the present compound 1(a) and the 2-chloro analog. BE values increase with herbicidal efficacy to a maxmimum value of 100.
  • BARNGR 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100
  • SIGNALGR 100 100 100 100 100 100 85
  • Compound I(a) is the compound of Example 2, 1-(4-chloro-2-fluoro-5-propargyloxyphenyl)-3-methyl-4-difluoromethyl- ⁇ 2 -1,2,4-triazolin-5-one.
  • BARNGR 100 100 100 100 100 100 BINDWEED 100 100 12 12 0 0 BLUE PAN 100 100 100 100 100 100 100 100 100 100 COCKLEBR 93 85 82 82 0 0 CORN 100 100 100 100 100 93 93
  • IVYGLORY 100 100 63 12 12 0
  • SIGNALGR 100 100 100 100 100 100 100 100 100 100 100 100 100 100
  • WMUSTARD 100 100 12 0 0 0
  • Compound A is 1-(2,4-dichloro-5-propargyloxyphenyl)- 3-methyl-4-difluoromethyyll- ⁇ 2 -1,2,4-triazolin-5-one.
  • BARNGR 100 100 100 100 100 85
  • Compound I(a) is the compound of Example 2, 1-(4-chloro-2-fluoro-5-propargyloxyphenyl)-3-methyl-4-difluoromethyl- ⁇ 2 -1,2,4-triazolin-5-one.
  • BARNGR 100 100 85 78 100
  • BINDWEED 100 100 65 12 100 BLUE PAN 100 100 100 100 100 100 100 100 100 100
  • SIGNALGR 100 100 100 100 100 100 100 100 100 100 100 100 100 100
  • Compound A is 1-(2,4-dichloro-5-propargyloxyphenyl)-3-methyl-4-difluoromethyl- ⁇ 2 -1,2,4-triazolin-5-one.
  • Table 5 shows a comparison of the average or overall biological efficacy for the present compound I(a) and the prior art compound against both weed grasses and weed broadleaves.
  • the BE values for grasses represent the average of the BE values in Table 3 (preemergence) or Table 4 (postemergence) for barnyardgrass, blue panicum, giant foxtail, green foxtail, johnsongrass, signalgrass, yellow nutsedge, and yellow foxtail.
  • the BE values for broadleaves represent the average for bindweed, cocklebur, ivyglory, sesbania, sicklepod, velvetleaf, and wild mustard.. As can be seen from the table, both compounds performed equally well against the grasses, but the present compound was substantially more active against the more difficult to control broadleaves.
  • phytotoxicity data were taken as percent control. Percent control was determined by a method similar to the 0 to 100 rating system disclosed in "Research Methods in Weed Science,” 2nd ed. , B. Truelove, Ed.; Southern Weed Science Society; Auburn University, Auburn, Alabama, 1977.
  • the present rating system is as follows:
  • Herbicidal data at selected application rates are given for the compounds of Examples 3-7 in Tables 6 and 7 below.
  • the test compounds are identified in the tables by Example numbers. In the tables "kg/ha” is kilograms per hectare and “% C” is percent control. *The compound number is the number of the Example in which the particular compound was prepared.
  • the active compounds as above defined are 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 formulation and mode of application of a toxicant may affect the activity of the material in a given application.
  • the present herbicidal compounds may be formulated as granules of relatively large particle size, water-soluble or water-dispersible 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 are usually applied either as sprays, dusts, or granules to the areas in which suppression of vegetation is desired.
  • sprays or dusts are most commonly used.
  • These formulations may contain as little as 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 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 dilutents.
  • Wettable powders normally are prepared to contain about 5-80% 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 a.s wetting agents. Frequently, additional wetting agent and/or oil will be added to the tank-mix for post-emergence application to facilitate dispersion on the foliage and absorption by the plant.
  • Emulsifiable concentrates 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 emulsifying agent, or may also contain a liquid carrier, such as xylene, heavy aromatic naphthas, isophorone, or other non-volatile organic solvent.
  • a liquid carrier such as xylene, heavy aromatic naphthas, isophorone, or other non-volatile organic solvent.
  • 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.
  • Typical wetting, dispersing or emulsifying agents used in agricultural formulations include, for example, the alkyl and alkylaryl sulfonates and sulfates and their sodium salts; polyhydric alcohols; and other types of surface active agents, many of which are available in commerce.
  • the surface active agent when used, normally comprises 1% to 15% by weight of the herbicidal composition.
  • compositions for herbicidal applications include simple solutions of the active ingredient in a dispersant in which it is completely soluble at the desired concentration, such as acetone, alkylated naphthalenes, xylene or other organic solvents.
  • Granular formulations, wherein the toxicant is carried on relatively coarse particles, are of particular utility for aerial distribution or for penetration of cover crop canopy.
  • Pressurized sprays typically aerosols wherein the active ingredient is dispersed in finely divided form as a result of vaporization of a low boiling dispersant solvent carrier, such as the Freons, may also be used.
  • Water-soluble or water-dispersible granules are also useful formulations for herbicidal application of the present compounds.
  • Such granular formulations are free-flowing, non-dusty, and readily water-soluble or water-miscible. These soluble or dispersible granular formulations described in U.S. patent No. 3,920,442, incorporated herein by reference are useful herein with the present herbicidal compounds.
  • the active herbicidal compounds of this invention may be formulated and/or applied with insecticides, fungicides, nematicides, plant growth regulators, fertilizers, or other agricultural chemicals and may be used as effective soil sterilants as well as selective herbicides in agriculture.
  • an effective amount and concentration of the active compound is of course employed.
  • the active herbicidal compounds of this invention may be used in combination with other herbicides, e.g. they 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-(methoxymethyl)acetamide (alachlor), 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-l-methylethyl)-acetamide (metolachlor), and N-chloroacetyl-N-(2,6-diethylphenyl)glycine (diethatyl-ethyl); benzothiadiazinone herbicides such as 3-(1-methylethyl)-(1H)-2,1,3-benzothiadiazin-4-(3H)-one-2,2-dioxide (bentazon); triazine herbicides such as 6-chloro-N
  • R is a radical selected from 2-propynyl, 1-methylethyl, 1-methyl-2-propynyl, methoxymethyl, 2-propenyl, and 1-methyl-2-methoxyethyl, may be prepared by (a) reacting the compound of the formula
  • R-X in which R is as defined above and X is a good leaving group, in the presence of a base, or alternatively, (b) reacting a compound of the formula
  • the base is an alkali metal carbonate, or alkali metal bicarbonate, or an alkali metal hydride
  • the phase transfer catalyst is a tetralkylammonium halide and the base is sodium hydroxide.
  • the base can be sodium carbonate or potassium carbonate and in method (b) the phase transfer catalyst is a tetrabutylammonium halide or a (triethyl)(benzyl)ammonium halide in which the halide is bromide or chloride.

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  • 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)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

Nouveaux composés d'aryltriazolinone de formule (I), où R représente un alkyle, un alcényle, un alcynyle, un alkoxyalkyle ou un alkyl-S(O)n-alkyle où n vaut de 0 à 2, qui ont une utilité herbicide contre une multitude de plantes herbeuses et à larges feuilles à la fois dans des applications de pré-émergence et de post-émergence, dont des exemples sont donnés par la catégorie où R représente un 2-propynyle, un 1-méthyléthyle, un 1-méthyl-2-propynyle, un méthoxyméthyle, un 2-propényle et un 1-méthyl-2-méthoxyéthyle.
EP19850901703 1984-03-29 1985-03-04 1-ARYLE--g(d)?2 -1,2,4-TRIAZOLINE-5-ONES HERBICIDES. Withdrawn EP0177553A4 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US59460284A 1984-03-29 1984-03-29
US594602 1984-03-29
US67329184A 1984-11-20 1984-11-20
US673291 1984-11-20

Publications (2)

Publication Number Publication Date
EP0177553A1 EP0177553A1 (fr) 1986-04-16
EP0177553A4 true EP0177553A4 (fr) 1986-08-21

Family

ID=27082025

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19850901703 Withdrawn EP0177553A4 (fr) 1984-03-29 1985-03-04 1-ARYLE--g(d)?2 -1,2,4-TRIAZOLINE-5-ONES HERBICIDES.

Country Status (8)

Country Link
EP (1) EP0177553A4 (fr)
AU (1) AU566839B2 (fr)
BR (1) BR8506209A (fr)
CA (1) CA1246589A (fr)
HU (1) HU194703B (fr)
IL (1) IL74737A0 (fr)
IT (1) IT1200433B (fr)
WO (1) WO1985004307A1 (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU573930B2 (en) * 1984-10-31 1988-06-23 Fmc Corporation Herbicidal aryl triazolinones
EP0220952A1 (fr) * 1985-10-26 1987-05-06 Nihon Nohyaku Co., Ltd. Procédé de préparation de dérivés de la triazoline-1,2,4 one-5 et produits intermédiaires à cette fin
AU572739B2 (en) * 1985-10-26 1988-05-12 Nihon Nohyaku Co., Ltd. 1,2,4-triazolin-5-one derivatives
JPS6299368A (ja) * 1985-10-26 1987-05-08 Nippon Nohyaku Co Ltd Δ↑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
JPH02500271A (ja) * 1986-08-20 1990-02-01 エフ エム シー コーポレーション 除草剤
JPS63150267A (ja) * 1986-12-16 1988-06-22 Showa Roodeia Kagaku Kk オキサジアゾロン誘導体及び除草剤
US4761174A (en) * 1987-04-14 1988-08-02 Fmc Corporation Triazolin-5-one herbicides
WO1988005264A1 (fr) * 1987-01-15 1988-07-28 Fmc Corporation Herbicides a base de triazoline-5-one
US4846875A (en) * 1987-07-21 1989-07-11 Fmc Corporation Herbicidal triazolinones
UA26918C2 (uk) 1988-08-31 1999-12-29 Фмк Корпорейшн Похідhі триазоліhоhу, що проявляють гербіцидhу активhість, гербіцидhа композиція, спосіб придушеhhя росту бур'яhів
DE19802697A1 (de) 1998-01-24 1999-07-29 Bayer Ag Selektive Herbizide auf Basis von N-Aryl-triazolin(thi)onen und N-Arylsulfonylamino(thio)carbonyltriazolin(thi)onen

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0069855A2 (fr) * 1981-05-29 1983-01-19 Sumitomo Chemical Company, Limited N-(fluoro-2-halogène-4-phéhyle substitué-5-)hydantoines, leurs préparation et application

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
CH651029A5 (de) * 1980-12-25 1985-08-30 Nihon Nohyaku Co Ltd Triazolin-derivate, verfahren zu ihrer herstellung und sie enthaltende herbizide mittel.
US4452981A (en) * 1981-09-19 1984-06-05 Sumitomo Chemical Company, Limited 4-(2-Fluoro-4-halo-5-substituted phenyl)urazols, and their production 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

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0069855A2 (fr) * 1981-05-29 1983-01-19 Sumitomo Chemical Company, Limited N-(fluoro-2-halogène-4-phéhyle substitué-5-)hydantoines, leurs préparation et application

Also Published As

Publication number Publication date
IT1200433B (it) 1989-01-18
HUT38220A (en) 1986-05-28
CA1246589A (fr) 1988-12-13
BR8506209A (pt) 1986-04-15
IT8520115A0 (it) 1985-03-27
IL74737A0 (en) 1985-06-30
WO1985004307A1 (fr) 1985-10-10
HU194703B (en) 1988-03-28
EP0177553A1 (fr) 1986-04-16
AU566839B2 (en) 1987-10-29
AU4115485A (en) 1985-11-01

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