EP0221083A1 - Triazolinones d'haloalkyle - Google Patents

Triazolinones d'haloalkyle

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Publication number
EP0221083A1
EP0221083A1 EP19860900971 EP86900971A EP0221083A1 EP 0221083 A1 EP0221083 A1 EP 0221083A1 EP 19860900971 EP19860900971 EP 19860900971 EP 86900971 A EP86900971 A EP 86900971A EP 0221083 A1 EP0221083 A1 EP 0221083A1
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EP
European Patent Office
Prior art keywords
group
alkyl
ring
aryl
haloalkyl
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Withdrawn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
EP19860900971
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German (de)
English (en)
Inventor
Lester Lawrence Maravetz
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FMC Corp
Original Assignee
FMC Corp
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Publication date
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Publication of EP0221083A1 publication Critical patent/EP0221083A1/fr
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • 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

Definitions

  • This invention relates to herbicidal 1-aryl- 4,5-dihydro-1,2,4-triazol-5(1H)-ones having a haloalkyl group on the carbon at the 3-position of the triazolinone ring.
  • R 1 is an alkyl group
  • R 2 is an alkynyl group, a halomethyl group, or a haloethyl group
  • X is an alkoxy group, an alkenyloxy group, an alkoxyalkoxy group, an alkynyloxy group, a hydroxy group, a halomethyloxy group, or a haloethyloxy group.
  • Japanese Kokai 107975 discloses herbicidal compounds of the formula
  • R 1 is 1-4C alkyl
  • R 2 is H, 1-4C alkyl, halomethyl or 3-4C alkynyl
  • X is Cl or F
  • Y is Cl, Br, OH or OR 3
  • R 3 is 1-4C alkyl or benzyl
  • Z is H, carboxy, cyanomethoxy, COOR 4 , COSR 5 or CON(R 6 ) (R 7 );
  • R 4 is 1-4C alkyl or 3-4C alkoxyalkyl
  • R 5 is 1-4C alkyl
  • R 6 and R 7 are H, 1-4C alkyl or alkoxy).
  • R 1 is C 1 -C 4 alkyl
  • R 2 is hydrogen, C 1 -C 6 alkyl or C 1 -C 4 alkenyl
  • X is hydroxy, C 1 -C 4 alkyl
  • R is a C 1 -C 4 alkyl group, a C 3 -C 4 alkenyl group or a C 3 -C 4 cycloalkyl group
  • X is a chlorine or bromine atom
  • Y is a hydrogen atom or a C 1 -C 4 alkoxy group.
  • the compounds of this invention are herbicidal aryl-4,5-dihydro-1,2,4-triazol-5(1H)-ones (such as those in the prior art, e.g. described above) in which, however, the carbon atom at the 3-position of the triazole ring carries a C 1 -C 4 haloalkyl group whose halogens are selected from F, Cl and Br, particularly a fluoroalkyl (e.g. difluoromethyl) group.
  • the compounds of the invention are those which have the following formula:
  • R 2 is said haloalkyl group and R 1 may be hydrogen, but preferably is alkyl (e.g. of 1 to 6, preferably 1 to 4, carbon atoms); haloalkyl (e.g. of 1 to 5, preferably 1 to 3, carbon atoms particularly fluoroalkyl); cyanoalkyl (e.g. of 2 to 5 carbon atoms, for example, cyanomethyl); alkenyl (e.g. of 2 to 5 carbon atoms such as 2-propenyl); alkynyl (e.g. of 2 to 5 carbon atoms such as 2-propynyl); alkoxyalkyl
  • alkylamino e.g. of 1 to 6 carbon atoms
  • alkoxy e.g. of 1 to 6, preferably 1 to 4, carbon atoms
  • haloalkenyl or haloalkynyl e.g. of 2 to 8 carbon atoms, for example
  • the aryl radical thus represents a group useful in the 1-aryl-4, 5-dihydro-1,2,4-triazol-5(lH)-one art to give herbicidal compounds when attached at the 1-position of an appropriate known 4,5-dihdyro-1,2,4-triazol-5(1H)-one.
  • any of the aryl radicals of the aforementioned patents may be used.
  • the Ar radical is preferably such that said 3-Methyl-4-Difluoromethyl Analog has marked herbicidal properties.
  • the 3-Methyl-4-Difluoromethyl Analogs of the preferred compounds show at least 50% kill of at least one of the following species of plants when applied under at least one of the following modes at the rate of 0.5 kg/ha, and more preferably show such kill of at least 50% when applied at the rate of 0.1 kg/ha: Species: velvetleaf (Abutilon theophrasti), green foxtail (Setaria viridis); Modes: pre-emergent, post-emergent. Testing for such herbicidal activity may be carried out in the manner described below (under the heading "Herbicidal Activity").
  • Ar is preferably a ring-substituted aryl radical.
  • Ar may have a benzene ring such as the radical indicated by the following formula
  • X 1 may be for instance hydrogen or halogen, preferably fluorine or chlorine, the halogen atom advantageously being positioned at the C-2 carbon atom of the phenyl ring;
  • X 2 may be hydrogen, halogen such as fluorine, chlorine, or bromine, alkyl of 1 to 6 (preferably 1 to 4) carbon atoms, particularly methyl, haloalkyl of 1 to 5 carbon atoms, for example, trifluoromethyl, alkoxy of 1 to 6 (preferably 1 to 4) carbon atoms;
  • Z may, for instance, be hydrogen; halogen such as fluorine, chlorine, or bromine; alkyl of 1 to 6 (preferably 1 to 4) carbon atoms; cyanoalkyl; haloalkyl of 1 to 5 carbon atoms; nitro; a group -OR; or a group -CO-R 6 or CH 2 CO-R 6 or CH( CH 3 )CO-R 6 ; or a group -OSO-R 9 ;
  • R may be hydrogen, alkyl of 1 to 6 (preferably 1 to 4) carbon atoms which may be substituted with cycloalkyl of 3 to 7 carbon atoms (for example, methyl or 1-methylethyl, or cyclohexylmethyl), cycloalkyl of 3 to 7 carbon atoms which may be substituted with alkyl of 1 to 6 carbon atoms (for example, cyclopentyl or methylcyclopropyl), alkoxyalkyl of 2 to 8 carbon atoms (for example, ethoxymethyl), cyanoalkyl of 2 to 7 carbon atoms such as cyanomethyl or 2-cyanoethyl, alkenyl of 2 to 5 carbon atoms such as 2-propenyl, alkynyl of 2 to 5 carbon atoms such as 2-propynyl, haloalkyl of 1 to 5 (preferably 1 to 3) carbon atoms especially a fluoroalkyl, haloalkenyl of 2 to 5 carbon
  • R 3 and R 4 may be independently hydrogen or alkyl or alkoxy of 1 to 4 carbon atoms, Q 1 is O, S or NR 7 wherein R 7 may be H or alkyl of 1 to 6
  • R 5 may be hydrogen, alkyl of 1 to 6 (preferably 1 to 4) carbon atoms, alkoxyalkyl or alkylthioalkyl of 2 to 6 carbon atoms, haloalkyl of 1 to 5 carbon atoms (especially fluoroalkyl or chloroalkyl), alkenyl of 2 to 5 carbon atoms such as 2-propenyl, cycloalkenyl of 5 to 7 carbon atoms which may be substituted with alkyl of 1 to 4 carbon atoms (for example, 2-cyclohexenyl), cyclohexenylalkyl of 6 to 10 carbon atoms (for example, 3-cyclohexenylmethyl), phenyl or benzyl (which may be ring-substituted with fluorine, chlorine, bromine, or alkyl, alkoxy, or alkylthio of 1 to 4 carbon atoms), cyanoalkyl of 2 to 7 carbon atoms
  • R 5 may additionally be alkoxy, alkylthio, or alkylsulfonyl, each of 1 to 6 carbon atoms, phenylsulfonyl, or phenylalkylsulfonyl of 1 to 3 alkyl carbon atom.
  • R of the -OR substituent may be a heterocyclic group or an alkyl radical substituted with a heterocyclic group.
  • the R group of this type may be any of those disclosed in my copending application Serial No. 655,960, filed September 28, 1984, and its parent application Serial No. 541,596, filed October 13, 1983, which disclose aryltriazolinones whose aryl groups have such -OR substituents (the present application is a continuation-in-part of both those applications and incorporates, by reference, their entire disclosures.)
  • the "Ar" radical of this invention may be any of the aryl radicals disclosed in those applications.
  • R groups on those aryl radicals, which may be employed are 1-methyl-3-pyrrolidinyl, furfuryl or 2-thienylmethyl, or preferably 3-tetrahydrofuranyl, tetrahydrofurfuryl, tetrahydropyran-2-ylmethyl, 1,3-dioxolan-2-ylmethyl, 2-(1,3-dioxolan-2-yl)ethyl, 2 ,2-dimethyl-1,3-dioxolan-4-yl-methyl, 3-(2-methyl-1,3-dioxolan-2-yl)propyl, 1,3-dioxan-4-ylmethyl, 1,4-benzodioxan-2-ylmethyl, tetrahydro-4H-pyran-4-yl, 5,6-dihydro-2H-pyran-3-ylmethyl, 2,2-dimethyl-1,3-dithiolan-4-ylmethyl, tetrahydro-4H
  • R 6 is hydroxy, alkoxy or alkylthio of 1 to 6 carbon atoms such as methoxy or methylthio, alkoxyalkoxy of 2 to 6 carbon atoms (for example, 2-methoxyethoxy), amino, or alkylamino or dialkylamino wherein each alkyl is of 1 to 6 (preferably 1 to 4) carbon atoms and may be substituted with alkoxy of 1 to 4 carbon atoms (for example, methylamino, dimethylamino, or (methyl) (2-methoxy- ethyl) amino).
  • R of the -OR substituent may be a group -CR 3 R 4 (CH 2 ) COQ 1 -R 5 .
  • Aryl triazolmones whose aryl radicals have such -OR substituents of this type are disclosed in my copending application Serial No. 666,933 filed October 31, 1984. (The present application is a continuation-in-part of that application, whose entire disclosure is incorporated herein by reference.)
  • the "Ar" radical of this invention may be any of the aryl radicals disclosed in that copending application.
  • Z may also be a group -OSO 2 R 9 where R 9 is alkyl, haloalkyl, cyanoalkyl, arylalkyl, cyclic alkyl, alkenyl, haloalkenyl, arylalkenyl, alkynyl, haloalkynyl, arylalkynyl, aryl, or a group of the formula -(CH 2 ) m NR 3' R 4' or -alkyl-Y-R 5' wherein m is 0 to 5; R 3' is hydrogen or alkyl; R 4' is alkyl or a group of the formula -alkyl-Y 3' -R 8' ; R 8' is alkyl, alkoxycarbonylalkyl, alkenyl, or alkynyl; and Y 3' is oxygen or S(O) r in which r is 0 to 2.
  • R 9 is alkyl, haloalkyl,
  • R 9 is methyl, ethyl, propyl, 1-methylethyl, butyl, 2-methylpropyl, 1-methylpropyl, 3-methylbutyl, chloromethyl, dichloromethyl, 3-chloropropyl, bromomethyl, difluoromethyl, trifluoromethyl, cyanomethyl, benzyl, cyclopropyl, 2-propenyl, 2,3,3-trichloro-2-propenyl, 2-propynyl, 3-bromo-2-propynyl, dimethylamino, dimethylaminoethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-(2-propenoxy)ethyl, 2-(2-propenthio)ethyl,
  • the aryl radical will be a dihalophenyl radical, preferably a 2,4-dihalophenyl radical, for example, a 5-(alkoxy or alkynyloxy of up to 6 carbon atoms) -2,4-dihalophenyl radical such as a 4-chloro-2-fluoro-5-(1-methylethoxy)phenyl or 4-chloro-2-fluoro-5-(2-propynyloxy)phenyl radical.
  • a dihalophenyl radical preferably a 2,4-dihalophenyl radical, for example, a 5-(alkoxy or alkynyloxy of up to 6 carbon atoms) -2,4-dihalophenyl radical such as a 4-chloro-2-fluoro-5-(1-methylethoxy)phenyl or 4-chloro-2-fluoro-5-(2-propynyloxy)phenyl radical.
  • any alkyl, alkenyl or alkynyl groups of the compound may be straight chain or branched chain radicals.
  • 1-methylethyl, 2-methyl-2-propenyl, and 1-methyl-2-propynyl are branched chain examples of alkyl, alkenyl, and alkynyl radicals respectively.
  • the halogen may be fluorine, chlorine, bromine or iodine.
  • the haloalkyl radical may have one or more same or different halogen atoms.
  • the substituents X 1 and X 2 are preferably both halogen, with
  • X 1 being fluorine or chlori.ne and X 2 being chlorine or bromine.
  • the X 1 halogen will usually be positioned at the C-2 carbon atom of the phenyl ring.
  • the compounds wherein X 1 is fluorine are particularly preferred.
  • the present compounds may be prepared by methods described in the literature or by methods analogous and similar thereto and within the skill of the art.
  • the ester of difluoroacetylcarbamic acid may then be converted into a 1-aryl-4,5-dihydro-3-difluoromethyl-1,2,4-triazol-5(1H)-one by reacting it with an aryl hydrazine, as illustrated in Step B of Example 1.
  • the aryl group of that hydrazine may carry all the substituents desired in the final compound (as is the case in the process for making compound 10 described at the end of Step B of Example 1) or those substituents, and any R 1 substituent, may be added in subsequent reactions, as illustrated in Steps C, D, E, F and G of Example 1.
  • One or both of the (halogen) substituents at the 2- and/or 4-position of the phenyl group may be introduced subsequently, e.g. by halogenating (as with SO 2 Cl 2 ) a 1-aryl-4,5-dihydro-3-difluoromethyl-4-methyl-1,2,4-triazol-5(1H)-one having hydrogen at one of those 2- and/or 4-positions and having any appropriate group at the 5-position of the phenyl group.
  • a haloacetonitrile such as F 2 HC-CN or F 3 C-CN or F 2 ClC-CN
  • F 2 HC-CN or F 3 C-CN or F 2 ClC-CN a haloacetonitrile
  • phosgene a 1-aryl-4,5-dihydro-3-polyhalomethyl-4,5-dihydro-1,2,4-triazol-5(1H)-one(as illustrated in Step B of Example 2).
  • Subsequent reactions may add an R 1 substituent at the 4-position of the 4,5-dihydro-1,2,4-triazol ring (as in Step C of Example 2) and/or vary the substituents on the aryl radical.
  • the 1-aryl group of such an intermediate may be a substituted phenyl radical identical with that present in the final compound or it may be a substituted phenyl radical containing an easily replaceable substituent (e.g., a methoxy group at the 5-position of the phenyl radical, as in a 5-methoxy-4-chloro(or bromo)-2-fluorophenyl radical) which phenyl radical can then be converted, by replacing that substituent, to the final substituted phenyl radical, preferably after first converting it to the corresponding phenolic radical (e.g. a 5-hydroxyphenyl radical).
  • an easily replaceable substituent e.g., a methoxy group at the 5-position of the phenyl radical, as in a 5-methoxy-4-chloro(or bromo)-2-fluorophenyl radical
  • the aryl group is to have a 2-F substituent it is preferred that the F substituent be present before formation of the heterocyclic ring
  • Step B 1-(4-Chloro-2-fluoro-5-methoxyphenyl)-3- difluoromethyl-4,5-dihydro-1,2,4-triazol- 5(1H)-one
  • 8.0 g (0.042 mole) of 4-chloro-2-fluoro-5-methoxyphenylhydrazine and 8.4 g (0.05 mole) of ethyl difluoroacetylcarbamate in 120 mL of xylene was added 2.1 g of phosphorus pentoxide. After complete addition the mixture was heated at reflux for one hour. While still hot, the reaction mixture was decanted from a dark residue into a clean flask.
  • the acidified aqueous mixture was stirred at room temperature forming a brown precipitate. Collection of the precipitate by filtration yielded 1.5 g of 1-(4-chloro-2-fluoro-5-methoxyphenyl)-3-difluoromethyl-4,5-dihydro-1,2,4-triazol-5(1H)-one.
  • the precipitate which was previously saved for purification was stirred in 70 mL of an aqueous 10% sodium hydroxide solution.
  • the basic mixture was filtered through a celite pad to remove insoluble materials.
  • the filtrate was acidified with concentrated hydrochloric acid producing a white solid. This solid was collected by filtration to yield an additional 0.7 g of product (mp 188-190°C).
  • Compound 10 1-[2,4-dichloro-5-(1-methylethoxy)-phenyl]-3-difluoromethyl-4,5-dihydro-1,2,4-triazol-5(lH)-one, and 1-(3-methoxyphenyl)-3-difluoromethyl-4,5-dihydro-1,2,4-triazol-5(1H)-one were prepared by the method of Example 1, Step B, from 2,4-dichloro- 5-(1-methylethoxy)phenylhydrazine or 3-methoxyphenylhydrazine, respectively.
  • the two phase mixture was filtered through a celite pad.
  • the organic phase was removed and was washed in succession with four portions of an aqueous 10% sodium hydroxide solution, and one portion each of an aqueous 10% hydrochloric acid solution, a saturated aqueous sodium carbonate solution, and water. After washing, the organic phase was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to yield 1.6 g of 1-(4-chloro-2-fluoro-5-methoxyphenyl)-3-difluoromethyl-4,5-dihydro-4-methyl-1,2,4-triazol-5(1H)-one. A portion of this material was recrystallized from ethanol and water to provide the product as a light tan solid (mp 127-129°C), Compound 22.
  • Compounds which contain a 4-difluoromethyl group may be prepared by a process analogous to Example 1, Step C, by reacting 1-(3-methoxyphenyl)-3-difluoromethyl-4,5-dihydro-1,2,4-triazol-5(1H)-one or 1-(2,4-dichloro-5-methoxyphenyl)-3-difluoromethyl-4,5-dihydro-1,2,4-triazol-5(1H)-one first with sodium hydroxide and tetrabutylammonium bromide in cyclohexane and tetrahydrofuran followed by chlorodifluoromethane.
  • Step D 1-(4-Chloro-2-fluoro-5-hydroxyphenyl)- 3-difluoromethyl-4,5-dihydro-4-methyl- 1,2,4-triazol-5(1H)-one
  • Step E tert-Butyl 2-[2-chloro-4-fluoro-5-(3- difluoromethyl-4,5-dihydro-4-methyl-5-oxo- 1H-1,2,4-triazol-l-yl)phenoxy]propionate
  • Step F 2-[2-Chloro-4-fluoro-5-(3-difluoromethyl- 4,5-dihydro-4-methyl-5-oxo-1H-1,2,4-triazol- 1-yl)phenoxy]propionic acid
  • the nmr was consistent with the proposed structure.
  • Step G N-(2-Chlorophenylsulfonyl) ⁇ 2-[2-chloro- 4-fluoro-5-(3-difluoromethyl-4, 5-dihydro- 4-methyl-5-oxo-1H-1,2,4-triazol-l-yl)- phenoxy]propionamide]
  • N-[2,4-dichloro-5-(1-methylethoxy)anilino]chlorodifluoroacetamidine and N-(4-chloro-2-fluoro-5-methoxyanilino)chlorodifluoroacetamidine were prepared by the process described in Example 2, Step A, from the correspond ingly substituted phenylhydrazine and chlorodifluoroacetonitrile.
  • Step B 1-[2,4-Dichloro-5-(1-methylethoxy)phenyl]- 3-trifluoromethyl-4, 5-dihydro-1,2,4-triazol- 5(1H)-one
  • the mixture was diluted with 25 mL of water and stirred vigorously for a brief period. Sufficient concentrated hydrochloric acid was added to make the aqueous phase acidic (pH 2). The acidic aqueous phase and the organic phase were shaken briskly after which the organic phase was separated from the mixture and saved for further purification.
  • the aqueous phase was extracted with methylene chloride and the extract evaporated to leave a yellow solid. This solid was dissolved in toluene and the resultant solution added to the saved organic phase from above.
  • the combined organic phase was stirred at room temperature with decolorizing carbon and filtered through a celite pad. The filtrate was extracted with a 1 N sodium hydroxide solution.
  • Compound 31 was prepared by the manner of Example 1, Step C, from Compound 30.
  • Compound 24 was prepared in an analogous manner from 1-[2,4-dichloro-5-(1-methylethoxy)phenyl]-3-chlorodifluoromethyl-4, 5-dihydro-1,2,4-triazol-5(1H)-one using potassium carbonate and acetone in place of sodium hydride and N,N-dimethyIformamide.
  • the plant tests species used in demonstrating the herbicidal activity of compounds of this invention include cotton (Gossypium hirsutum var. Stoneville), soybean (Glycine max var. Williams), field corn (Zea mays var. Agway 595S), wheat (Triticum aestivium var.
  • Prodax field bindweed (Convolvulus arvensis), morningglory (Ipomeea lacunosa or Ipomea hederacea, velvetleaf (Abutilon theophrasti), barnyardgrass (Echinochloa crus galli), green foxtail (Setaria viridis), johnsongrass ( Sorghum halepense), yellow nutsedge (Cyperus esculentus), and rice (Oryza sativa).
  • Seeds or tubers of the plant test species were planted in furrows in steam sterilized sandy loam soil contained in disposable fiber flats.
  • a topping soil of equal portions of sand and sandy loam soil was placed uniformly on top of each flat to a depth of approximately 0.5 cm.
  • the flats for the preemergence test 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.
  • the flats for the postemergence test were placed in a greenhouse and watered for 8-10 days, then the foliage of the emerged test plants was sprayed with a solution of the test compound in acetone-water containing up to 0.5% sorbitan monolaurate. After spraying the foliage was kept dry for 24 hours, then watered regularly for 21 days, and phytotoxicity data recorded.
  • 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:
  • BARNYARDGRASS 100 60 100 100 100
  • BARNYARDGRASS 100 100 100 60
  • BARNYARDGRASS 100 80 100 100
  • BARNYARDGRASS 100 0 100 100
  • BARNYARDGRASS 100 0 100 100
  • BARNYARDGRASS 100 100 80 100
  • BARNYARDGRASS 100 80 100 100
  • 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 in 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 cotton seed 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 diluents. 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 as wetting agents. Frequently, additional wetting agent and/or oil will be added to the tank-mix for postempergence 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.
  • the soluble or dispersible granular formulations described in U.S. patent No. 3,920,442 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 selec tive 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-(1-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-

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
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  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
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Abstract

1-aryl-1,2,4-triazolin-5(1H)-ones herbicides possédant un groupe haloalkyle (par ex. CHF2, CF3 ou CClF2) lié à l'atome de carbone en position 3 du cycle triazolinone.
EP19860900971 1985-02-04 1986-01-21 Triazolinones d'haloalkyle Withdrawn EP0221083A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US69761985A 1985-02-04 1985-02-04
US697619 1985-02-04

Publications (1)

Publication Number Publication Date
EP0221083A1 true EP0221083A1 (fr) 1987-05-13

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ID=24801847

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19860900971 Withdrawn EP0221083A1 (fr) 1985-02-04 1986-01-21 Triazolinones d'haloalkyle

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EP (1) EP0221083A1 (fr)
AU (1) AU5358886A (fr)
CA (1) CA1281724C (fr)
WO (1) WO1986004481A2 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU572739B2 (en) * 1985-10-26 1988-05-12 Nihon Nohyaku Co., Ltd. 1,2,4-triazolin-5-one derivatives
CA1331463C (fr) * 1988-08-31 1994-08-16 Kathleen Megan Poss Triazolinones herbicides
US5125958A (en) * 1988-08-31 1992-06-30 Fmc Corporation Herbicidal triazolinones
DE4303676A1 (de) * 1993-02-09 1994-08-11 Bayer Ag 1-Aryltriazolin(thi)one
DE4309966A1 (de) * 1993-03-26 1994-09-29 Bayer Ag Substituierte 1-Aryltriazolinone
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

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Publication number Publication date
CA1281724C (fr) 1991-03-19
AU5358886A (en) 1986-08-26
WO1986004481A2 (fr) 1986-08-14

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