EP0452367A1 - Compositions distribuables contenant des pesticides - Google Patents

Compositions distribuables contenant des pesticides

Info

Publication number
EP0452367A1
EP0452367A1 EP90901471A EP90901471A EP0452367A1 EP 0452367 A1 EP0452367 A1 EP 0452367A1 EP 90901471 A EP90901471 A EP 90901471A EP 90901471 A EP90901471 A EP 90901471A EP 0452367 A1 EP0452367 A1 EP 0452367A1
Authority
EP
European Patent Office
Prior art keywords
composition
pesticide
emulsion
amount
water
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.)
Pending
Application number
EP90901471A
Other languages
German (de)
English (en)
Inventor
Conrad Walter Ebe
Lawrence Richard Lebeau
Lucia Garcia-Iniguez Marshall
James Michael Warner
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.)
Monsanto Co
Original Assignee
Monsanto Co
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 Monsanto Co filed Critical Monsanto Co
Publication of EP0452367A1 publication Critical patent/EP0452367A1/fr
Pending 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • 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

  • This invention relates to a pesticide compo.- sition including herbicide, fungicide, insecticide and acaracide compositions. More particularly, this invention relates to a herbicidal composition suitable for being applied by rotary dispensation and even more particularly relates to an oil-in-water emulsion con- taining a pyridinedicarboxylic herbicide suitable for being applied to kill or control plants by rotary dis ⁇ pensation'. Other methods of application include spraying or distributing using a garden hose attachment or other spray apparatus. In employing a hose and applicator, the applicator is attached to the distribution end of a hose (or pipe) so that direction may be imparted to the composition exiting the hose. If desired, flexible or rigid hose or conveyor or distributor of liquid may be employed.
  • Substituted pyridinecarboxylic acid and derivatives thereof are known to have a wide range of preemergence and postemergence activity as herbicides. Such herbicides are disclosed in U.S. Patent No.
  • This is accomplished by feeding a composition of this invention to a device provided with a distribution element that discharges the composition of this invention in a controlled manner onto a defined area of plants or to any desired locus.
  • British Patent Specification No. 2,131,327 discloses illustrative spray equipment useful for deposition of compositions of this invention. Difficulties are encountered in obtaining a uniform spray when prior art spray mixtures are em ⁇ ployed using a device designed to discharge a herbi ⁇ cidal mixture from a distribution element by rotary dispensation.
  • the present invention provides a co po- sition suitable for but not limited to being applied directly by rotary dispensation.
  • pyridine herbicide compositions are known, they do not possess the characteristics to make stable, water dispersible emulsions with low animal toxicity and with maximum effectiveness in low pressure spraying lances in which the composition is distributed to plants or other desired targets from a rotary distribution element.
  • Some prior art oil/water emulsions for plant protection mixtures have used phospholipids and phospholipid/oil aqueous formulations, together with fatty acid ethoxylates, hydrogenated castor oils, nonylphenol, or fatty acid amides, or with a inoalcohols as coemulsifiers.
  • the present invention provides a composition which is suitable for being directly applied to plants or to ground and is especially suitable for rotary dispensation.
  • the composition is an oil-in-water emulsion containing a nonpolar agriculturally accept ⁇ able pesticide in an agriculturally effective amount.
  • the composition is especially useful when the nonpolar pesticide is pyridinedicarboxylic herbicide.
  • the composition contains a fatty oil, such as a long chain fatty acid, preferably methyl oleate or methyl laurate, in an amount sufficient to dissolve the pesticide(s) .
  • Water is used in the composition which will be the carrier for any polar pesticide.
  • An amphipathic lipid is present in the compositions.
  • the term "amphipathic lipid” includes a phospholipid, a glycolipid, a sphingolipid or a ceramide.
  • Illustrative preferred examples include those lipids having a hydrophillic "head” group and a hydrophobic "tail” group and have membrane forming capability.
  • Illustrative lipids include those recited on pages 9-10 of CRC Handbook of Biochemistry and Molecular Biology, 3rd Edition, Gerald D. Fasman, 1975. Use of an emulsifier and/or surfactant is optional.
  • the pesticide is present in the composition in an amount of about 1 to about 30 weight percent based on the weight of the composition. More preferably, the pesticide is present in the composition in an amount of about 2-25 weight percent based on the weight of the composition.
  • the long chain fatty oil solvent is present in the composition in amounts of about 0-80 weight percent based on the weight of the composition.
  • the fatty oil solvent is present in the composition in an amount of about 15-35 weight percent based on the weight of the composition.
  • the amphipatic lipid is present in the composition in an amount of about 1-25 weight percent based on the weight of the emulsion. More preferably, the lipid is present in the composition in an amount of about 3-12 weight percent based on the weight of the composition. Water is present in the composition in an amount of about 25-96 weight percent based on the weight of the composition. More preferably, water is present in the composition in an amount of about 50-80 weight percent based on the weight of the composition. The amount of oil-in-water emulsifier and/or surfactant is sufficient to render the emulsion stable.
  • the emulsifier such as a glycerol monostearate derivative, and/or surfactant, such as ammonium lauryl sulfate or sodium dodecyl benzene sulfate, is optionally present in the composition in an amount of about 0.5 to 20 weight percent based on the weight of the composition. More preferably, the emulsifier and/or surfactant is present in the composition in an amount of about 0.5-5 weight percent based on the weight of the composition.
  • adjuvants may be present in the compo ⁇ sition. If desired for example, it is often preferred that a biocide be included in the composition to mini- mize the buildup of microorganisms. In order to prevent freezing of the composition, an antifreeze agent may be incorporated in the composition. The incorporation of an antifoam agent is often used to reduce air locks in some spray equipment.
  • the herbicidally active pyridinedicarboxylic acid is most preferably a
  • R is selected from the group consisting of lower alkyl, lower alkenyl, lower alkynyl, lower alkenylalkyl, haloalkyl, haloalkenyl, C 3 7 cycloalkyl, C 3 6 cycloalkanylalkyl, C 3 6 cycloalkenyl, aryl, arylmethyl, alkoxyalkyl, benzyloxymethyl, alkylthio- alkyl, dialkoxyalkyl, (l-alkoxy-l-alkylthio)-alkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkyl- sulfonylalkyl, alkylsulfinylalkyl, alkyl substituted with a dialkyl sulfonium salt, cyanoalkyl, carbamyl- alkyl, carbalkoxyalkyl, carbalkoxyalkenyl, formyl- al
  • Z is selected from O and NR 7 where R 7 is hydrogen or lower alkyl, and wherein Z 2 is selected from O and S wherein R 3 in each occurrence is inde ⁇ pendently selected from hydrogen, alkyl C x 4 , alkenyl- alkyl C 3 4 , haloalkyl C x 4 , cycloalkanylalkyl, cyanoalkyl, or alkynylalkyl C 3 4 ;
  • R. is selected from hydrogen and halogen
  • R 5 and R 6 are independently selected from hydrogen, lower alkyl, and phenyl; -CH 2 OH; and -C ⁇ N.
  • Compounds which are of particular interest as herbicides include those wherein X and Y are both ester groups in which R 3 in each-ester group -is inde ⁇ pendently an alkyl group having 1-3 carbon atoms.
  • a more preferred grouping includes those compounds in which Rj_ and R 2 are dissimilar fluorinated methyl radicals; and within this more preferred grouping, the most preferred compounds are those in which R is an alkyl or alkylthioalkyl substituent having 1-5 carbon atoms.
  • alkyl means herein both straight and branched chain radicals which include, but are not limited to, ethyl, methyl, n-propyl, 1-ethylpropyl,
  • cycloalkyl is intended to mean cycloalkyl radicals, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl.
  • lower alkyl herein means an alkyl radical having 1 to 7 carbon atoms.
  • lower alkenyl and “lower alkynyl” herein means alkenyl and alkynyl groups having 2 to 7 carbon atoms. Examples of such alkenyl groups include ethenyl, 1-propenyl,
  • saturated and unsaturated hetero ⁇ cyclic radical means heterocyclic radicals having from 3 to 6 atoms in the ring including from 1 to 3 hetero atoms selected form O, S and N, and typically include, but are not limited to, furyl, pyridyl, thienyl, thioranyl, oxiranyl, and aziridinyl.
  • cycloalkanylalkyl is intended to mean alkyl radicals substituted with a C 3 _ 6 cycloalkyl radical.
  • haloalkyl is intended to mean alkyl radicals substituted with one or more halogen atoms.
  • fluorinated methyl means herein methyl radicals having one or more fluorine atoms attached thereto including radicals wherein all hydrogen atoms are substituted by fluorine.
  • chlorofluorinated methyl means herein methyl radicals having at least one hydrogen substituted by fluorine and at least one other hydrogen substituted by chlorine.
  • Illustrative pesticides which may be employed herein include any pesticide either oil or water soluble.
  • Illustrative pesticides include herbicides, fungicides and insecticides, mixtures thereof and the like. More than one pesticide may be employed if desired.
  • An example of a preferred insecticide is chlorpyrifos.
  • a preferred fungicide is pentachloronitrobenzene.
  • fatty acid solvents recommended for the preparation of the compositions of the present invention are saturated or olefinically unsaturated fatty acids with 2-20 carbon atoms. Acids with 12-18 carbon atoms are preferred. More preferably are the alkyl esters of such acids. Particularly suitable are the lower alkyl esters, such as methyl esters of the fatty acids.
  • compositions of the present invention as adjuvants or auxiliary agents are natural or synthetic lipids.
  • Particularly preferred are phos- pholipids or mixtures of purified phospholipids, such as phosphatidyl choline, phosphatidyl ethanolamine, N-acyl phosphatidyl ethanolamine, phosphatidyl serine and other phosphatides.
  • composition of the present invention optionally contains an effective amount of a suitable surfactant and/or emulsifier.
  • surfactants include alkyl sulfate and alkylbenzenesulfonic acid, particularly lauryl sulfate and dodecylbenzenesulfonic acid.
  • the surfactant contains a range of alkyl groups with the name designating the length of the alkyl group being derived from the average length of the alkyl group.
  • the lauryl and the dodecyl groups referred to herein have an average of about 12 carbon atoms.
  • the length and branching of the alkyl chain can vary.
  • Another suitable surfactant is ammonium lauryl sulfate with 3 ethoxide units.
  • the emulsifier be an alkoxylated partial ester of glycerol, e.g., glycerol monostearate condensed with about 3 to 30 or more moles of ethylene oxide, propylene oxide or mixtures thereof.
  • GMS Ethoxylated glycerol monostearate
  • Neodol Ammonium lauryl sulfate (3 EO) surfactant
  • compositions which show no separation at -20°C and 50°C are most preferred. "— ,r represent border ⁇ line separation situations.
  • the measured viscosities are set forth in
  • Flow rates of each composition were measured using a NOMIX Trim and Edge illustrated in Monsanto booklet No. 154-88-LOIR equipped with a rotary dispen- sator dispenser. Approximately 800 grams of each emulsion was placed inside a plastic bag. Each bag was sealed and connected to the device. During spraying the bag was positioned 1.02 meters above the exit of the composition from the dispenser. The dispenser was primed by allowing the emulsion to flow out of its dispensing head (without a disk on the head) for at least 30 seconds. Once the head was primed, flow rate measurements were made by releasing the emulsion from the device for 30 seconds.
  • the amount of released emulsion was measured; and the emulsion flow rate was expressed in terms of grams per minute. Flow rates for each formulation were measured at five different dispensing settings. In Table 6 the determined flow rates in grams per minute are set forth.
  • compositions of the present invention can be used to dispense centri- fugally a pesticide in a carefully controlled manner.
  • Kentucky 31 tall fescue is grown from un ⁇ treated certified seed in square green plastic pots 10 cm and 7 cm wide at the top and bottom, respectively, and 9 cm high.
  • the soil mix is composed of one third 0 silt loam, two thirds Redi-earth soil conditioner by volume and 2.4 kilograms per cubic meter IBDU 31-0-0 slow release fertilizer. After thorough mixing, the soil medium is heat sterilized. Pots are filled with soil mix to the top of the pot and pressed lightly to 1 cm below the top. Adequate seed is broadcast evenly and covered with approximately 0.4 cm of the soil mix.
  • Common bermudagrass is grown from untreated certified seed. Planting procedure for common ber ⁇ mudagrass is identical to tall fescue.
  • Sweet clover is grown from seed in the same size pots as the grasses.
  • the soil mix is Metro Mix 350. Pots are filled with soil mix, leveled at the top of the pots, and compressed lightly to 1 cm below the top. Adequate seed is broadcast evenly and covered with approximately 0.4 cm of soil mix.
  • Common dandelion is grown from untreated seed. Planting procedure for common dandelion is identical to that of sweet clover.
  • the greenhouse for tall fescus is maintained at a day/night temperature of approximately 14/18°C.
  • the greenhouse for common bermudagrass, sweet clover and common dandelion is maintained at a day/night temperature of approximately 29/24°C.
  • Photoperiod for all plant species during fall, winter and spring is 12 hours. During summer, the natural photoperiod is used. Approximately 3 weeks after planting, plants are mowed to a uniform height of 6 cm. Tall fescue and bermudagrass are mowed 3 times per week. Sweet clover and common dandelion are mowed once each week. Plant material is mowed with a modified electric mower-vacuum device that removes clippings * The mower is mounted on top of the greenhouse bench and moves along the length of the bench.
  • Optimum soil moisture levels are maintained by hand irrigation with tap water. Water used for irrigation is maintained as close as possible to room air temperature. Large-oscillating fans are used to ventilate the greenhouses to insure that the plant shoots dry soon after irrigation thus reducing disease potential.
  • Fungicides and insecticides are applied on an as needed basis. Fungicides are chosen based on time of year that specific diseases are expected to be a problem. Fungicides and insecticides are applied according to manufacturer's label recommendations. Plants utilized for treatment are 8 weeks old. This age plant responds well to chemical appli ⁇ cation yet exhibits sufficient physiological and mor ⁇ phological maturity for good translation of greenhouse to field test.
  • Soil/pan preparation The fifty percent Ray silt loam/fifty percent Redi-earth soil mixture (v/v) used in this test has an OM content of 2.4 per ⁇ cent, does not crust, and holds its shape when pressed into the pans. The soil moisture contains no fertilizer and the entire soil mixture is steam sterilized.
  • pans are filled on an as needed basis. The day before chemical treatment, pans are planted with seeds or vegetative propagules of the appropriate species, covered, and packed with the previously described soil mixture to within 6.4 mm of the top of the pan.
  • Formulations (B) and (C) are oil based formulations.

Landscapes

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

Abstract

On a mis au point une composition de pesticides que l'on peut appliquer directement à des plantes par pulvérisation. Ladite composition est une émulsion d'huile en eau contenant un pesticide non polaire acceptable dans l'agriculture en quantité efficace. Ladite composition est particulièrement utile lorsque le pesticide non polaire est un herbicide pyridinedicarboxylique. La composition contient une huile grasse, telle qu'un acide gras à chaîne longue, de préférence de l'oléate méthylique ou du laurate méthylique, en quantité suffisante pour dissoudre le ou les pesticides. On utilise de l'eau dans la composition, faisant office de support pour n'importe quel pesticide polaire. Les compositions comprennent un lipide amphipathique. L'emploi d'un émulsifiant et/ou d'un tensio-actif est facultatif.
EP90901471A 1988-12-27 1989-12-21 Compositions distribuables contenant des pesticides Pending EP0452367A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US29013488A 1988-12-27 1988-12-27
US290134 1988-12-27
US43705789A 1989-11-21 1989-11-21
US437057 1995-05-09

Publications (1)

Publication Number Publication Date
EP0452367A1 true EP0452367A1 (fr) 1991-10-23

Family

ID=26966023

Family Applications (2)

Application Number Title Priority Date Filing Date
EP89870208A Withdrawn EP0379851A1 (fr) 1988-12-27 1989-12-21 Compositions distribuables contenant un pesticide
EP90901471A Pending EP0452367A1 (fr) 1988-12-27 1989-12-21 Compositions distribuables contenant des pesticides

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP89870208A Withdrawn EP0379851A1 (fr) 1988-12-27 1989-12-21 Compositions distribuables contenant un pesticide

Country Status (10)

Country Link
EP (2) EP0379851A1 (fr)
JP (1) JPH04502915A (fr)
KR (1) KR910700001A (fr)
AU (1) AU4845490A (fr)
BR (1) BR8907861A (fr)
CA (1) CA2006571A1 (fr)
IL (1) IL92892A0 (fr)
MY (1) MY129945A (fr)
NZ (1) NZ231949A (fr)
WO (1) WO1990007272A1 (fr)

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US5084087A (en) * 1989-04-26 1992-01-28 Basf Corporation Ready to dilute adjuvant-containing postemergent herbicide formulations
GB9016783D0 (en) * 1989-09-01 1990-09-12 Ici Plc Agrochemical compositions
AU8869391A (en) * 1991-08-19 1993-03-16 Church & Dwight Company, Inc. Broad-spectrum biocompatible fungicides
GB9319129D0 (en) * 1993-09-15 1993-11-03 Dowelanco Ltd Storage and dilution of stable aqueous dispersions
FI96166C (fi) * 1994-03-01 1996-05-27 Kemira Agro Oy Torjunta-ainekoostumuksen valmistusmenetelmä
CA2186625A1 (fr) * 1994-04-05 1995-10-12 James Franklin Essinger, Jr. Preparation amelioree de formulations dispersees dans l'eau par nucleation et cristallisation d'un principe actif pesticide a bas point de fusion
IT1275167B (it) * 1995-02-23 1997-07-30 Isagro Spa Adiuvanti per fungicidi sistemici composizioni fungicide che li contengono e loro impiego
ES2182048T3 (es) 1996-10-25 2003-03-01 Monsanto Technology Llc Composicion y procedimiento para tratar plantas con sustancias quimicas exogenas.
PT936860E (pt) * 1996-10-25 2002-07-31 Monsanto Technology Llc Composicao e metodo para tratamento de plantas com quimicos exogenos
AUPQ017599A0 (en) 1999-05-05 1999-05-27 Victorian Chemicals International Pty Ltd Adjuvant composition for chemicals used in agriculture
AUPQ579800A0 (en) 2000-02-23 2000-03-16 Victorian Chemicals International Pty Ltd Plant growth hormone compositions
DK1333721T3 (da) 2000-10-17 2006-08-28 Victorian Chemical Internat Pt Herbicidpræparat
CA2472806A1 (fr) 2004-05-18 2005-11-18 Petro-Canada Compositions et methodes de traitement d'insectes nuisibles de pelouse et de maladies telles qu'infestations fongiques
US9357768B2 (en) 2006-10-05 2016-06-07 Suncor Energy Inc. Herbicidal composition with increased herbicidal efficacy
WO2008143990A1 (fr) * 2007-05-18 2008-11-27 Valent Biosciences Corporation Formulations d'huile de cannelle et procédés d'utilisation
CN102215692B (zh) 2008-06-26 2014-10-22 森科能源公司 含有颜料的改良型草坪草杀真菌制剂
US8808762B2 (en) 2008-10-17 2014-08-19 Valent Biosciences Corporation Cinnamaldehyde and diallyl disulfide formulations and methods of use
EP2346338A4 (fr) * 2008-10-17 2013-07-10 Valent Biosciences Corp Compositions contenant de l'essence de cannelle (et/ou son composant principal, le cinnamaldéhyde) et du disulfure de diallyle, leur formulation et leurs procédés d'utilisation
WO2012031355A1 (fr) 2010-09-09 2012-03-15 Suncor Energy Inc. Huile paraffinique synergique et fongicides de boscalide
CN103732071A (zh) 2011-06-03 2014-04-16 桑科能源股份有限公司 用于控制由真菌病原体引起的作物感染的水包石蜡油型乳剂
JP2015522554A (ja) 2012-06-04 2015-08-06 サンコー・エナジー・インコーポレーテッド パラフィン油及び沈降防止剤を含む製剤
CA2889198C (fr) * 2012-10-23 2023-02-21 Rhodia Operations Compositions de pesticide aqueux comprenant un agent de controle des depots gras
MX2021008944A (es) 2019-01-25 2021-08-24 Suncor Energy Inc Compuestos fotosensibilizadores, metodos de fabricacion y aplicacion a las plantas.
AU2020222515B2 (en) 2019-02-15 2025-10-09 Nutrien Ag Solutions (Canada) Inc. The use of protoporphyrin IX derivatives to improve the health of plants

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NL6701139A (fr) * 1967-01-25 1968-07-26
DE3125399A1 (de) * 1981-06-27 1983-01-13 A. Nattermann & Cie GmbH, 5000 Köln Neue herbizid-zusammensetzung, verfahren zur herstellung und deren verwendung
DE3225705A1 (de) * 1982-07-09 1984-01-12 A. Nattermann & Cie GmbH, 5000 Köln Verfahren zum ausbringen von pflanzenschutzmittelspritzbruehen durch verspruehen und verpackungseinheit fuer konzentrate
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Also Published As

Publication number Publication date
JPH04502915A (ja) 1992-05-28
WO1990007272A1 (fr) 1990-07-12
IL92892A0 (en) 1990-09-17
EP0379851A1 (fr) 1990-08-01
KR910700001A (ko) 1991-03-13
BR8907861A (pt) 1991-11-12
CA2006571A1 (fr) 1990-06-27
AU4845490A (en) 1990-08-01
MY129945A (en) 2007-05-31
NZ231949A (en) 1993-02-25

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