EP0603336A1 - Combinaison synergique de derives d'acide aryloxypropionique herbicides et de cyclohexanediones - Google Patents

Combinaison synergique de derives d'acide aryloxypropionique herbicides et de cyclohexanediones

Info

Publication number
EP0603336A1
EP0603336A1 EP92920871A EP92920871A EP0603336A1 EP 0603336 A1 EP0603336 A1 EP 0603336A1 EP 92920871 A EP92920871 A EP 92920871A EP 92920871 A EP92920871 A EP 92920871A EP 0603336 A1 EP0603336 A1 EP 0603336A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
substituted
alkoxy
halogen
hydrogen
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.)
Ceased
Application number
EP92920871A
Other languages
German (de)
English (en)
Inventor
S. Robert Colby
John Stephen Casey
James Anderson
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.)
Zeneca Inc
Original Assignee
Zeneca Ltd
Zeneca Inc
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 Zeneca Ltd, Zeneca Inc filed Critical Zeneca Ltd
Publication of EP0603336A1 publication Critical patent/EP0603336A1/fr
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings

Definitions

  • compositions comprising:
  • X is hydrogen or halogen
  • R 1 is hydrogen, C 1 -C 8 alkyl, C 1 -C 6 alkoxyalkyl
  • R is independently hydrogen; halogen; nitro; cyano; C 1 -C 6 alkyl; C 1 -C 6 alkyl substituted with a substituent
  • halogen selected from the group consisting of halogen, nitro, hydroxy, C 1 -C 6 alkoxy and C 1 -C 6 alkylthio; C 2 -C 6 alkenyl; C 2 -C 6 alkynyl; hydroxy; C 1 -C 6 alkoxy; C 1 -C 6 alkoxy substituted with a substituent selected from halogen and C 1 -C 6 alkoxy; C 2 -C 6 alkenyl- oxy; C 2 -C 6 alkynyloxy; C 2 -C 6 alkanoyloxy; (C 1 -C 6 alkoxy)- carbonyl; C 1 - C6 alkylthio; C 1 -C 6 alkylsulfinyl; C 1 -C 6 alkyl- sulfonyl; sulfamoyl; N-C( 1 -C 6 alkyl) sulfamoyl; N,N-di (C 1 -
  • R 9 and R10 are independently selected from the group consisting of hydrogen, C 1 -C 6 alkyl, C 2 -C 6 alkanoyl, benzoyl and benzyl; the groups formyl and C 2 -C 6 alkanoxyl and the oxime, imine and Schiff base derivatives thereof; and at least one of X is not selected from the group consisting of halogen, C 1 -C 6 alkyl and C 1 -C 6 alkoxy;
  • R 2 is C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, a substituted C 1 -C 6 alkyl, substituted with halogen, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, phenyl, substituted phenyl wherein the phenyl is substituted with halogen, nitro, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl,
  • R 3 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 fluoroalkyl,
  • R 4 is hydrogen or the keto tautomer; C 1 -C 6 alkyl;
  • alkylthio C 1 -C 6 alkoxycarbonyl, phenyl, and substituted phenyl wherein the benzene ring is substituted with 1 to 3 substituents selected from the group consisting of halogen, nitro, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, and C 1 -C 6 alkylthio; C 1 -C 6 (alkyl) sulfonyl; benzene sulfonyl;
  • substituted benzene sulfonyl wherein the benzene ring is substituted with 1 to 3 substituents selected from the group consisting of halogen, nitro, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy and C 1 -C 6 alkylthio; an acyl group and an inorganic or organic cation; and
  • n is an integer chosen from 2 to 5.
  • alkyl alkoxy
  • alkenyl alkylthio
  • aryloxypropionic acid derivatives useful in the present invention are:
  • Preferred cyclohexanediones included in the present invention are those in which the phenyl group is substituted with methyl groups and include:
  • 6-position of the phenyl ring and are preferably selected from halogen, methyl and methoxy.
  • herbicide is used herein to denote a compound which controls or modifies the growth of plants.
  • herbicidally effective amount is used to indicate the quantity of such a compound or combination of such compounds which is capable of producing a controlling or modifying effect. Controlling or modifying effects include all deviations from natural development, for example: kill, retardation, leaf burn, dwarfing and the like.
  • plant refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage and fruits.
  • the aryloxy- propionic acid derivative:cyclohexanedione weight ratio at which the herbicidal response is synergistic lies within the range of 1:5 to about 30:1, preferably about 1:5 to about 15:1 and most preferably about 1:2 to about 8:1.
  • compositions of the invention are most efficiently employed at a rate of 0.001 to 50 pounds per acre (0.001 to 56 kilograms per hectare), preferably 0,001 to 25 pounds per acre (0.001 to 28 kilograms per hectare).
  • Plastic pots were filled with 2 parts sandy loam and 1 part peat moss mixed together containing the commercial fungicide cis-N[(trichloromethyl)thio]-4-cyclohexene-1,2- dicarboximide (Captan ® ) and 17-17-17 fertilizer (percentages of N-P 2 O 5 -K 2 O on a weight basis). Each pot was seeded to a single plant species. The plant species included giant
  • foxtail (Setaria faberi) and shattercane (Sorghum vulgare).
  • the pots were placed in a greenhouse for approximately two weeks where they were watered regularly.
  • the greenhouse temperature was approximately 85° F. day and 80° F. night.
  • nonionic emulsifier methyl capped derivative of Renex 650
  • Aerosol OT 100 30 g/l
  • Formula tion (b) included Herbicide (B) , 125 g/l; emulsifier 50 g/l; made up to 1.0 liter with Solvesso 100; and formulation (c) included Herbicide (C), 125 g/l; non-ionic emulsifier, 110 g/l; anisole, 400 g/l made up to 1.0 liter with Solvesso 150.
  • Pots in the greenhouse were seeded with large crabgrass (Digitaria sanguinalis), barnyardgrass (Echinochloa crusgalli), goosegrass (Eleusine indica), guineagrass (Panicum maximum), and johnsongrass (Sorghum halepense).
  • each plant species had 4 - 5 leaves per plant.
  • the above formulations were blended and the final solution blended with 0.1% by weight of AGRAL 90 an 1.0% by weight of ACTIPON.
  • the final solution was applied through a greenhouse track sprayer at a volume of 200 liters per hectare.
  • compositions of this invention are useful as herbicides demonstrating synergistic activity for the control of undesirable vegetation.
  • the compositions can be formulated in the same manner in which herbicides are generally formulated.
  • the compounds may be applied either separately or combined as part of a two-part herbicidal system.
  • the object of the formulation is to apply the compositions to the locus where control is desired by a convenient method.
  • the "locus" is intended to include soil, seeds, and seedlings, as well as established vegetation.
  • Formulations will generally contain several additives. Among these are some inert ingredients and diluent carriers such as organic solvents, water, oil and water, water in oil emulsions, carriers of dust and granules, and surface active, wetting, dispersing, and emulsifying agents. Fertilizers, such as ammonium nitrate, urea, potash and superphosphates may also be added. Aids to rooting and growth, such as compost, manure, humus, sand, etc. may likewise be added.
  • inert ingredients and diluent carriers such as organic solvents, water, oil and water, water in oil emulsions, carriers of dust and granules, and surface active, wetting, dispersing, and emulsifying agents.
  • Fertilizers such as ammonium nitrate, urea, potash and superphosphates may also be added. Aids to rooting and growth, such as compost, manure, humus,
  • the formulations are commonly dusts, wettable powders, granules, solutions or emulsifiable concentrates.
  • Dusts are free-flowing powder compositions containing the herbicidal compound impregnated on a particulate carrier.
  • the particle size of the carrier is usually in the approximate range of 30 to 50 microns.
  • suitable carriers are talc, bentonite, diatomaceous earth, and pyrophyl lite.
  • Anticaking and antistatic agents can be added, if desired.
  • the composition generally contains up to 50% of active ingredient. Dusts, like liquid compositions, can be applied by spraying from boom sprayers, hand sprayers or airplanes.
  • Wettable powders are finely divided compositions comprising a particulate carrier impregnated with the herbicidal compound and additionally containing one or more surface active agents.
  • the surface active agent promotes rapid
  • a wide variety of surface active agents can be used, for example, long chain fatty alcohols; salts of sulfonic acid; esters of long chain fatty acids; and polyhydric alcohols, in which the alcohol groups are free, omega-substituted polyethylene glycols of relatively long chain length.
  • Granules comprise the herbicidal composition impregnated on a particulate inert carrier having a particle size of about 1 to 2 millimeters in diameter.
  • the granules can be made by spraying a solution of the active ingredient in a volatile solvent onto the granular carrier.
  • Suitable carriers in preparation of granules include clay, vermiculite, sawdust, granular carbon, etc.
  • Microcapsules and other slow release formulations are advantageous as formulations to deliver and distribute the active ingredients.
  • Microcapsules consist of fully enclosed droplets or granules containing the active materials in which the enclosing material is an inert porous membrane, arranged to allow escape of the enclosed materials to the surrounding medium at controlled rates over a specified period of time.
  • Encapsulated droplets are typically about 1 to 50 microns in diameter.
  • the enclosed liquid typically constitutes about 50 to 95% of the weight of the entire capsule, and may contain an amount of solvent in addition to the active materials.
  • Encapsulated granules are characterized by porous membranes sealing the openings of the granule carrier pores, trapping the liquid containing the active components inside for controlled release.
  • a typical granule size ranges from 1 millimeter to 1 centimeter in diameter. In agricultural usage, the granule size is generally about 1 to 2 millimeters in diameter.
  • Granules formed by extrusion, agglomeration or prilling are useful in the present invention as well as materials in their naturally occurring form. Examples of such carriers are vermiculite, starch sintered clay granules, kaolin, attapul- gite clay, sawdust and granular carbon.
  • Useful encapsulating materials include natural and synthetic rubbers, cellulosic materials, styrene-butadiene copolymers, polyacrylonitriles, polyacrylates, polyesters, polyamides, polyureas, polyurethanes and starch xanthates.
  • the herbicidal compositions can also be applied to the soil in the form of a solution in a suitable solvent.
  • Solvents frequently used in herbicidal formulations include kerosene, fuel oil, xylene, petroleum fractions with boiling ranges above xylene, and aromatic petroleum fractions rich in methylated naphthalenes.
  • Emulsifiable concentrates consist of an oil solution of the herbicide along with an emulsifying agent. Prior to use, the concentrate is diluted with water to form a suspended emulsion of oil droplets.
  • the emulsifiers used are usually a mixture of anionic and nonionic surfactants. Other additives such as spreading agents and stickers can be included in the emulsifiable concentrate. It is not necessary that the compositions be admixed with the soil particles. After application by the above- discussed methods, they may be distributed below the soil surface to a depth of at least one-half inch by conventional means such as discing, dragging, or mixing.

Abstract

L'invention se rapporte à une composition herbicide synergique, qui comprend: (a) un dérivé d'acide aryloxypropionique, représenté par la formule (I), et (b) un dérivé de cyclohexanedione, représenté par la formule (II).
EP92920871A 1991-09-12 1992-09-11 Combinaison synergique de derives d'acide aryloxypropionique herbicides et de cyclohexanediones Ceased EP0603336A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US75803891A 1991-09-12 1991-09-12
US758038 1991-09-12
PCT/US1992/007709 WO1993004581A1 (fr) 1991-09-12 1992-09-11 Combinaison synergique de derives d'acide aryloxypropionique herbicides et de cyclohexanediones

Publications (1)

Publication Number Publication Date
EP0603336A1 true EP0603336A1 (fr) 1994-06-29

Family

ID=25050234

Family Applications (1)

Application Number Title Priority Date Filing Date
EP92920871A Ceased EP0603336A1 (fr) 1991-09-12 1992-09-11 Combinaison synergique de derives d'acide aryloxypropionique herbicides et de cyclohexanediones

Country Status (9)

Country Link
EP (1) EP0603336A1 (fr)
AU (1) AU658452B2 (fr)
BR (1) BR9206485A (fr)
CA (1) CA2118794C (fr)
MX (1) MX9205213A (fr)
NZ (1) NZ244308A (fr)
TW (1) TW213410B (fr)
WO (1) WO1993004581A1 (fr)
ZA (1) ZA926934B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SK283945B6 (sk) * 1995-09-20 2004-05-04 Basf Aktiengesellschaft Herbicídna zmes obsahujúca cyklohexenonoximéter, herbicídny prostriedok, spôsob jeho prípravy a použitie
GB9717321D0 (en) * 1997-08-15 1997-10-22 Zeneca Ltd Herbicidal composition

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TR19824A (tr) * 1977-07-21 1980-01-24 Ishihara Sangyo Kaisha Trilorometilpiridoksifenoksipropionik as tuerevleri ve bunlari ihtiva eden herbisidler
GB2026865A (en) * 1978-03-01 1980-02-13 Ici Ltd Herbicides
NZ202284A (en) * 1981-11-20 1986-06-11 Ici Australia Ltd 2-(1-(alkoxyimino)alkyl)-3-hydroxy-5-poly(methyl)phenyl-cyclohex-2-en-1-ones and herbicidal compositions
GB8702613D0 (en) * 1987-02-05 1987-03-11 Ici Plc Compositions

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9304581A1 *

Also Published As

Publication number Publication date
CA2118794A1 (fr) 1993-03-18
AU2677692A (en) 1993-04-05
TW213410B (fr) 1993-09-21
CA2118794C (fr) 2002-12-24
WO1993004581A1 (fr) 1993-03-18
BR9206485A (pt) 1995-10-24
AU658452B2 (en) 1995-04-13
ZA926934B (en) 1994-03-11
MX9205213A (es) 1993-06-01
NZ244308A (en) 1995-04-27

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