EP2124564A1 - Mélanges d'engrais insecticides - Google Patents

Mélanges d'engrais insecticides

Info

Publication number
EP2124564A1
EP2124564A1 EP07702642A EP07702642A EP2124564A1 EP 2124564 A1 EP2124564 A1 EP 2124564A1 EP 07702642 A EP07702642 A EP 07702642A EP 07702642 A EP07702642 A EP 07702642A EP 2124564 A1 EP2124564 A1 EP 2124564A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
haloalkyl
fertilizer
optionally
halogen
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Withdrawn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
EP07702642A
Other languages
German (de)
English (en)
Inventor
Reed Nathan Royalty
Britt Baker
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.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
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 Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP2124564A1 publication Critical patent/EP2124564A1/fr
Withdrawn legal-status Critical Current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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • A01N61/00—Biocides, pest repellants or attractants, or plant growth regulators containing substances of unknown or undetermined composition, e.g. substances characterised only by the mode of action
    • C—CHEMISTRY; METALLURGY
    • C05—FERTILISERS; MANUFACTURE THEREOF
    • C05G—MIXTURES OF FERTILISERS COVERED INDIVIDUALLY BY DIFFERENT SUBCLASSES OF CLASS C05; MIXTURES OF ONE OR MORE FERTILISERS WITH MATERIALS NOT HAVING A SPECIFIC FERTILISING ACTIVITY, e.g. PESTICIDES, SOIL-CONDITIONERS, WETTING AGENTS; FERTILISERS CHARACTERISED BY THEIR FORM
    • C05G3/00—Mixtures of one or more fertilisers with additives not having a specially fertilising activity
    • C05G3/60—Biocides or preservatives, e.g. disinfectants, pesticides or herbicides; Pest repellants or attractants

Definitions

  • This invention relates to stable and efficacious insecticidal fertilizer mixtures comprising a fertilizing component and an agonist or antagonist of ion channels in the insect nervous system.
  • Agonists and antagonists of ion channels in the insect nervous system are known. It is also known to use fertilizers in granular form for broadcast application to turfgrass and to use fertilizers for ornamental houseplants in the form of small fertilizer sticks or impregnated cardboard strips that are pressed into the nutrient substrate of the plants. Also known are mixtures of fertilizer granules with insecticides and/or other pesticide products for treatment of turfgrass and tablets containing dimethoate as insecticidal active substance and fertilizer for treatment of ornamental houseplants, but the action of such mixtures is not completely satisfactory. For example, U.S.
  • Patent 5,783,203 describes mixtures containing fertilizers and agonists or antagonists of nicotinergic acetylcholine receptors of insects, but the method described therein, while useful in part because it can provide increased uptake of pesticidally active components into plants, has not been found useful for preparing granular fertilizer mixtures that effectively and rapidly release ion channel agonists or antagonists into the soil.
  • Liquid fertilizer systems such as those containing agonists or antagonists of nicotinergic acetylcholine receptors described in U.S. Patent Application Serial No. 11/041 ,167, are also known but are not useful for solid fertilizer systems.
  • This invention relates to insecticidal fertilizer mixtures comprising (a) an agonist or antagonist of ion channels in the insect nervous system;
  • This invention further relates to dimensionally stable mixtures of agonists or antagonists of ion channels in the insect nervous system with fertilizers, optional adherents, and optional auxiliaries and carrier materials in the form of small sticks, plates, tablets or granules, which increase the speed of action of the agonist or antagonist.
  • the action of the mixtures according to the invention begins more rapidly than customary fertilizer-free granules containing the same active ingredient.
  • the mixtures according to the invention can be employed simply and without problems, specifically in non-commercial horticulture.
  • Active ingredients that are effective according to the invention include agonists or antagonists of ion channels, such as GABA-gated or glutamate-gated chloride (Cl " ) channels, in the insect nervous system.
  • ion channels such as GABA-gated or glutamate-gated chloride (Cl " ) channels
  • suitable ion channel agonists are arylpyrazoles of formula (I)
  • X represents N or C-R 6
  • R 1 is CN, methyl, or halogen
  • R 2 is S(O) n R 7 , 4,5-dicyanoimidazol 2-yl, or haloalkyl
  • R 3 represents hydrogen, halogen, NR 8 R 9 , S(O) m R 10 , C(O)R 10 ,
  • R 5 represents halogen, haloalkyl, haloalkoxy, S(O) q CF 3 , or SF 5
  • R 7 is alkyl or haloalkyl
  • R 8 and R 9 independently represent hydrogen, alkyl, haloalkyl, C(O)alkyl, alkoxycarbonyl, or S(O) r CF 3 ; or R 8 and R 9 together optionally form a divalent alkylene radical that is optionally interrupted by one or two divalent heteroatoms, such as oxygen or sulphur, Rio represents alkyl or haloalkyl,
  • Rn represents hydrogen, alkyl, or haloalkyl
  • R-I2 represents hydrogen or alkyl
  • R-I 3 represents phenyl or heteroaryl that is unsubstituted or optionally substituted by one or more halogen atoms or a member selected from the group consisting of OH, -O-alkyl, -S-alkyl, cyano, and alkyl, and m, n, q, and r, independently of one another, represent O 1 1 , or 2.
  • Alkyl groups preferably have 1 to 6 carbon atoms and include, for example, methyl, ethyl, i-propyl, and sec- or t.-butyl.
  • Haloalkyl groups preferably have 1 to 4 (more preferably 1 or 2) carbon atoms and preferably 1 to 5 (more preferably 1 to 3) halogen atoms, where the halogen atoms are identical or different and are preferably fluorine, chlorine, or bromine (more preferably fluorine), and include, for example, trifluoromethyl.
  • Alkoxy groups preferably have 1 to 4 (more preferably 1 or 2) carbon atoms and include, for example, methoxy, ethoxy, n- and i-propyloxy, and n-, i- and t-butyloxy
  • R 1 is methyl
  • R 1 is methyl
  • X is N
  • R 3 is NH 2
  • R 4 is Cl
  • R 5 is CF 3
  • R 7 is haloalkyl
  • X is C-Cl
  • R 2 is 4,5-dicyanoimidazol-2-yl
  • R 3 is Cl
  • R 4 is Cl
  • R 5 is CF 3
  • a more preferred group of effective 1-arylpyrazoles of the invention is that wherein X is C-R 6 ; R 1 is CN; R 3 is NH 2 ; R 4 and R 6 , independently of one another, represent halogen; R 5 is haloalkyl; and R 7 is haloalkyl.
  • a most preferred 1-arylpyrazole is 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4- trifluoromethylsulfinyl-3-cyanopyrazole.
  • the contents of active substance are preferably from about 0.0001 % to about 1%, preferably from about 0.001% to about 0.1%, and more preferably from about 0.005% to about 0.015%.
  • Suitable fertilizer components include organic and inorganic nitrogen-containing compounds such as urea, urea-formaldehyde condensation products, amino acids, ammonium salts and nitrates, as well as potassium salts (preferably chlorides, sulfates, or nitrates) and phosphoric acid and/or salts of phosphoric acids (preferably potassium salts or ammonium salts).
  • the fertilizers may also contain salts of micronutrients (preferably manganese, magnesium, iron, boron, copper, zinc, molybdenum, and/or cobalt) and phytohormones (e.g., vitamin B1 or indole-3-acetic acid). Commercially available complete fertilizers are preferably employed.
  • the principal fertilizer constituents, nitrogen, potassium, and phosphorus, can be varied within wide limits. It is conventional to use contents of from 1 to 30% of nitrogen (preferably from 5 to 20%), from 1 to 20% of potassium (preferably from 3 to 15%), and from 1 to 20% of phosphorus (preferably from 3 to 10%).
  • the contents of microelements are usually in the ppm range, preferably from 1 to 1000 ppm.
  • the adherent component serves to establish and/or maintain physical contact between the fertilizer component and the other components of the insecticidal fertilizer mixtures of the invention. When the agonist or antagonist component is soluble in a liquid adherent, the agonist or antagonist component can be initially dissolved or suspended in the adherent and then applied to the fertilizer by any conventional method, such as spraying or simple mixing.
  • all of the components can first be mixed together until essentially homogenous, after which the adherent is applied in a manner that does not lead to excessive aggregation of solid particles (when the agonist or antagonist component and the fertilizer are solids) or to separation of liquid from solid components (when the agonist or antagonist component is liquid).
  • Suitable adherents are typically retained on the resultant insecticidal fertilizer mixtures, but it is also possible to use adherents that evaporate or are washed away as long as they serve to establish and/or maintain physical contact between components (a) and (b).
  • Suitable adherents include known organic adhesives, including tackifiers, such as celluloses or substituted celluloses, natural and synthetic polymers in the form of powders, granules, or latices, and inorganic adhesives such as gypsum, silica, or cement.
  • tackifiers such as celluloses or substituted celluloses, natural and synthetic polymers in the form of powders, granules, or latices
  • inorganic adhesives such as gypsum, silica, or cement.
  • Particularly preferred adherents of this type are citric acid esters, such as Citroflex® esters.
  • organic or inorganic liquids that dissolve or suspend the agonist or antagonist component but do not persist in substantial quantities, such as water, alcohols, esters, ketones, ethers, aromatics, and other known liquids.
  • the insecticidal fertilizer mixtures of the invention retain little if any of the adherent once the mixtures are prepared.
  • the adherent is generally present in the mixture in concentrations of from 1 to 30% by weight, preferably from 2 to 20% by weight.
  • Suitable solid carrier materials include, for example, natural ground minerals, such as kaolins, aluminas, talc, chalk, quartz, attapulgite, montmorillonite, and diatomaceous earth, or synthetic ground minerals, such as highly dispersed silicic acid, aluminum oxide, silicates, and calcium phosphates and calcium hydrogen phosphates.
  • Suitable solid carrier materials for granules include, for example, crushed and fractionated natural minerals, such as calcite, marble, pumice, sepiolite, and dolomite, or synthetic granules of inorganic and organic ground materials, as well as granules of organic material, such as sawdust, coconut husks, corn cobs, and tobacco stalks.
  • Coated fertilizers can also be used.
  • Suitable auxiliaries for the preparation of the mixtures according to the invention include disintegrants and surfactants.
  • Disintegrants are used to promote the release of the active substance in the soil.
  • Corn starch, crosslinked polyvinylpyrrolidone, and specific celluloses can be used individually or in combination.
  • Disintegrants are present in concentrations of from 1 to 20% by weight, preferably from 3 to 10% by weight.
  • Surfactants are used to improve the biological activity of the active substance by solubilization.
  • Surfactants are present at a content between 1 to 10% by weight, preferably from 2 to 5% by weight.
  • Nonionic surfactants of the alkyl-aryl-ethoxylate type are appropriate.
  • Granular fertilizers are particularly preferred.
  • the mixtures of active substance, fertilizers, adhesive, auxiliary, and inert substances can, if desired, be mixed intensively and compressed by an extruder into small sticks with a diameter of from 3 to 10 mm, preferably from 6 to 8 mm, and a length of from 1 to 10 cm, preferably from 3 to 6 cm.
  • the mixture can be brought into the desired form of small sticks using a tableting press. It is also possible to produce small sticks or tablets that are free from active substance and then to coat these sticks or tablets with a solution of the active substance. This subsequent coating operation can also be used with advantage to apply active substance to fertilizer granules.
  • the fertilizer mixtures according to the invention are suitable for the control of insects that are encountered in horticulture, agriculture, and forestry.
  • the fertilizer mixtures are active against normally sensitive and resistant species and against all or individual stages of development.
  • the above-mentioned pests include the following:
  • Ctenocephalides felis Ctenocephalides canis, Pulex irritans, Spilopsyllus cuniculi, Tunga penetrans, and Xenopsylla cheopis.
  • the Siphonaptera for example, Ctenocephalides felis, Ctenocephalides canis, Pulex irritans, Spilopsyllus cuniculi, Tunga penetrans, and Xenopsylla cheopis.
  • Rhipicephalus sanguineus Ixodes pacificus, Ixodes scapularis, Amblyomma americanum, Amblyomma maculatum, Dermatocentor andersoni, Dermatocentor variabilis, Haemaphysalis chordeilis, and Boophilus annulatus.
  • Isopoda for example, Oniscus asellus, Armadil- lidium vulgare and Porecellio scaber.
  • Diplopoda for example, Blaniulus guttulatus.
  • Thysanura for example, Lepisma saccharina.
  • Thysanoptera From the order of the Thysanoptera, for example, Hercinothrips femoralis and Thrips tabaci.
  • compositions according to the invention are employed in a dose such that from about 0.01 to 100 mg/m 2 of active substance, preferably from 0.1 to 10 mg/m 2 of active substance and particularly preferably from 0.1 to 5 mg/m 2 of active substance, are employed.
  • the fertilizers used in the examples were 15-2-15, 0-0-7, and 24-8-15 fertilizers.
  • Granular formulations were prepared by dissolving technical grade fipronil in the Citroflex A-4 and then spraying the resultant mixture onto the fertilizer. Mixtures having a content of 72 ppm fipronil were used in the tests described in the following Examples. Stability Long-term stability of a mixture prepared in this manner was determined by comparing analyses of a blend of three samples conducted immediately after preparation and three years after preparation. The initial content of fipronil was found to be 0.0073%, whereas the content after three years was found to be 0.0066%.
  • Plots size varied but each plot contained at least ten fire ant mounds per plot.
  • the plots were treated in early summer. Numbers of live mounds in each plot were counted prior to treatment. Three replicates of each treatment were tested.
  • Granular formulations of fipronil and 12-2-15 fertilizer according to the invention were compared with granular formulations of fipronil on a Biodac® cellulose-based granular carrier. Efficacy was assessed at 12, 29, and 104 DAT (through early fall) by counting live mounds and calculating the percent reduction in mounds relative to the pretreatment counts. Results are presented in Table 2.

Landscapes

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

Abstract

La présente invention concerne des mélanges d'engrais insecticides contenant (a) un agoniste ou un antagoniste des canaux ioniques dans le système nerveux des insectes ; (b) un engrais ; (c) en option, un adhésif ; et (d) en option, un ou plusieurs auxiliaires et/ou véhicules.
EP07702642A 2007-01-10 2007-01-10 Mélanges d'engrais insecticides Withdrawn EP2124564A1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/EP2007/000138 WO2008083709A1 (fr) 2007-01-10 2007-01-10 Mélanges d'engrais insecticides

Publications (1)

Publication Number Publication Date
EP2124564A1 true EP2124564A1 (fr) 2009-12-02

Family

ID=38566057

Family Applications (1)

Application Number Title Priority Date Filing Date
EP07702642A Withdrawn EP2124564A1 (fr) 2007-01-10 2007-01-10 Mélanges d'engrais insecticides

Country Status (2)

Country Link
EP (1) EP2124564A1 (fr)
WO (1) WO2008083709A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2496389B (en) * 2011-11-08 2016-06-15 Rotam Agrochem Int Co Ltd Method for reducing the phytotoxic effects of N-aryl pyrazole insecticides

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5472712A (en) * 1991-12-24 1995-12-05 Euroceltique, S.A. Controlled-release formulations coated with aqueous dispersions of ethylcellulose
DE4412833A1 (de) * 1994-04-14 1995-10-19 Bayer Ag Insektizide Düngemischungen
JP2000191407A (ja) * 1998-12-25 2000-07-11 Nissan Chem Ind Ltd 被覆農業用組成物
ITMI20012509A1 (it) * 2001-11-29 2003-05-29 Agroqualita S R L Composizione microgranulare ad azione combinata fertilizzante e fitoprotettiva
US9919979B2 (en) * 2005-01-21 2018-03-20 Bayer Cropscience Lp Fertilizer-compatible composition

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2008083709A1 *

Also Published As

Publication number Publication date
WO2008083709A1 (fr) 2008-07-17

Similar Documents

Publication Publication Date Title
US5783203A (en) Insecticidal fertilizer mixtures
CN1104197C (zh) 杀虫剂组合物
KR20000028735A (ko) 살충 및 살비 활성 배합물
DE4412834A1 (de) Insektizide Mischungen
WO2015011704A1 (fr) Compositions insecticides compatibles avec des engrais
JP4007613B2 (ja) 有害生物防除剤としての置換ｎ−メチレンチオ尿素
CA2570706C (fr) Melanges d'engrais insecticides
EP2124564A1 (fr) Mélanges d'engrais insecticides
DE4005114A1 (de) Substituierte pyrazolinderivate
DE19540948A1 (de) Insektizide Mittel
KR0167337B1 (ko) 살충조성물
US4965255A (en) Carboximide containing agents for combating pests
US5114965A (en) Flubenzimine containing agents for combating pests
CN1891045A (zh) 杀虫剂组合物
MXPA97010368A (es) N-metilentioureas substituidas como agentes pesticidas

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20090810

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU LV MC NL PL PT RO SE SI SK TR

RIN1 Information on inventor provided before grant (corrected)

Inventor name: BAKER, BRITT

Inventor name: ROYALTY, REED, NATHAN

DAX Request for extension of the european patent (deleted)
17Q First examination report despatched

Effective date: 20101126

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN

18W Application withdrawn

Effective date: 20120427