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WO1996036618A1 - Oxadiazines pesticides - Google Patents

Oxadiazines pesticides Download PDF

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Publication number
WO1996036618A1
WO1996036618A1 PCT/US1995/006270 US9506270W WO9636618A1 WO 1996036618 A1 WO1996036618 A1 WO 1996036618A1 US 9506270 W US9506270 W US 9506270W WO 9636618 A1 WO9636618 A1 WO 9636618A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
haloalkyl
recited
compounds
halogen
Prior art date
Application number
PCT/US1995/006270
Other languages
English (en)
Inventor
Mark Achiel Kekeyser
Paul Thomas Mcdonald
Original Assignee
Uniroyal Chemical Company, Inc.
Uniroyal Chemical Ltd./Uniroyal Chemical Ltee
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 Uniroyal Chemical Company, Inc., Uniroyal Chemical Ltd./Uniroyal Chemical Ltee filed Critical Uniroyal Chemical Company, Inc.
Priority to EP95920514A priority Critical patent/EP0825990A1/fr
Priority to PCT/US1995/006270 priority patent/WO1996036618A1/fr
Priority to BR9510594-8A priority patent/BR9510594A/pt
Priority to KR1019970708149A priority patent/KR100417794B1/ko
Priority to JP53477896A priority patent/JP3210676B2/ja
Priority to AU25943/95A priority patent/AU697128B2/en
Publication of WO1996036618A1 publication Critical patent/WO1996036618A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
    • C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
    • C07D273/04—Six-membered rings
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/88—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with three ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • A01N47/08—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 one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof

Definitions

  • This invention is directed to substituted oxadiazines, which compounds exhibit unexpectedly desirable activity as pesticides, including as insecticides and acaricides.
  • this invention is directed to pesticidal compositions comprising such compounds as well as to methods of controlling pests employing such compounds and/or compositions.
  • acarids and insects present a serious problem to agriculture.
  • a wide variety of field crops are in need of protection from acarids and/or insects including such valuable crops as soybeans, corn, peanuts, cotton, alfalfa and tobacco.
  • vegetables such as tomatoes, potatoes, peas, sugarbeet, carrots and the like, as well as fruits, nuts, ornamentals and seed bed crops such as apples, peaches, citrus fruit, almonds and grapes may also require protection from the ravages of such pests.
  • Med. Chem, 1966, 753-758 refers to various 2-substituted 4H-1, 3, 4-oxadiazines said to have anticonvulsant activity in mice.
  • U.S. Patent 3,420,826 refers to certain 2,4, 6-substituted 4H-1, 3,4-oxadiazines, said to have utility as sedatives, anticonvulsants, and as pesticides, specifically against nematodes, plants, and fungi.
  • U.S. Patent 3,420,825 refers to methods for producing those compounds.
  • x is an integer from 0 to 4
  • n is an integer from 0 to 5 and R is defined below; or b)
  • n is an integer from 0 to 5 and R is defined below;
  • R is selected from the group consisting of: hydrogen; C 1 -C 4 alkyl; C ⁇ C j alkoxy; halogen; nitro; phenyl; cyano; phenoxy; benzyloxy; benzyl; C ⁇ dialkylamino; C 1 -C 4 alkylthio; C 1 -C 4 haloalkoxy; or C x -C 4 haloalkyl; and
  • R 1 is a C 1 -C 4 haloalkyl other than a chloroalkyl, preferably a C 1 -C 4 fluoroalkyl, or a group of the formula
  • R 4 is hydrogen, halogen, C 1 -C 4 haloalkyl or C- L -Q J haloalkoxy, preferably a group of the formula
  • compositions of this invention are comprised of (A) one or more compounds having the structure of formula I above, and (B) a suitable carrier.
  • suitable carriers may be solid or liquid in nature.
  • the compounds and compositions of the present invention exhibit pesticidal activity, especially against insects and acarids.
  • bases include alkali metal hydroxides.
  • Preferred bases include sodium or potassium hydroxide.
  • compositions of the present invention may be prepared by formulating one or more compounds of the present invention with a suitable carrier, such as a liquid or solid carrier.
  • Suitable liquid carriers may be comprised of water, alcohols, ketones, phenols, toluene and xylenes.
  • additives conventionally employed in the art may be utilized, such as one or more surface active agent ' s and/or inert diluents, to facilitate handling and application of the resulting pesticide composition.
  • the pesticidal compounds may be applied in liquid or sprays when utilized in a liquid carrier, such as in a solution comprising a compatible solvent such as acetone, benzene, toluene or kerosene, or as dispersed in a suitable non-solvent medium such as water.
  • the pesticidal compositions may alternatively comprise solid carriers taking the form of dusts, granules, wettable powders, pastes, aerosols, emulsions, emulsifiable concentrates, and water-soluble solids.
  • the pesticidal compounds of this invention may be applied as dusts when admixed with or absorbed onto powdered solid carriers, such as mineral silicates, e.g., mica, talc, pyrophyllite and clays, together with a surface-active dispersing agent so that a wettable powder is obtained which then is applied directly to the loci to be treated.
  • the powdered solid carrier containing the compound admixed therewith may be dispersed in water to form a suspension for application in such form.
  • Granular formulations of the compounds are preferred for field treatment and are suitable for application by broadcasting, side dressing, soil incorporation or seed treatment, and are suitably prepared using a granular or pellitized form of carrier such as granular clays, vermiculite, charcoal or corn cobs.
  • carrier such as granular clays, vermiculite, charcoal or corn cobs.
  • the pesticide is dissolved in a solvent and sprayed onto an inert mineral carrier such as attapulgite granules (10-100 mesh) , and the solvent is then evaporated.
  • Such granular compositions may contain from 2-25% pesticide based on carrier plus pesticide, with 3-15% being preferred.
  • the pesticide may also be incorporated into a polymeric carrier such as polyethylene, polypropylene, butadiene-styrene, styrene-acryonitrile resins, polyamides, poly(vinyl acetates) and the like.
  • a polymeric carrier such as polyethylene, polypropylene, butadiene-styrene, styrene-acryonitrile resins, polyamides, poly(vinyl acetates) and the like.
  • the pesticide may advantageously be released over an even longer time period, extending its effectiveness further than when used in non-encapsulated form.
  • Aerosol treatment Another method of application to loci to be treated is aerosol treatment, for which the compound may be dissolved in an aerosol carrier which is a liquid under pressure but which is a gas at ordinary temperature (e.g., 20°C) and atmospheric pressure. Aerosol formulations may also be prepared by first dissolving the compound in a less volatile solvent and then admixing the resulting solution with a highly volatile liquid aerosol carrier.
  • the compounds of the invention preferably are applied in aqueous emulsions containing a surface-active dispersing agent which may be non-ionic, cationic or anionic. Suitable surface-active agents are well known in the art, and include those disclosed in
  • the compounds may be employed with carriers which themselves are pesticidally active, such as insecticides, acaricides, fungicides or bactericides.
  • pesticidally active compound such as insecticides, acaricides, fungicides or bactericides.
  • concentrations of the compound as the active ingredient in pesticidally effective formulations may range from about 0.1 to about 95 percent by weight.
  • Spray dilutions may be as low as a few parts per million, while at the opposite extreme, full strength concentrates of the compound may be usefully applied by ultra low volume techniques.
  • concentration per unit area may range between about 0.01 and about 50 pounds per acre, with concentrations of between about 0.1 and about 10 pounds per acre preferably being employed for crops such as corn, tobacco, rice and the like.
  • sprays of the compounds may be applied to any suitable locus, such as to the pests directly and/or to plants upon which they feed or nest.
  • the pesticidally active formulations may also be applied to the soil or other medium in which the pests are present. Harmful insects and acarids attack a wide variety of plants, including both ornamental and agricultural plants and inflict damage by consuming roots and/or foliage, withdrawing vital juices from the plants, secreting toxins and often by transmitting diseases .
  • the compounds of the present invention may be advantageously utilized to minimize or prevent such damage.
  • the specific methods of application, as well as the selection and concentration of these compounds will of course vary depending upon such circumstances as geographic area, climate, topography, plant tolerance, etc. For specific circumstances, one skilled in the art may readily determine the proper compound, concentration and method of application by routine experimentation.
  • the compounds of the invention are particularly useful as insecticides and acaricides for foliar application.
  • the compounds are particularly effective for controlling insects, such as tobacco budworm and mites, such as spider mites and rust mites.
  • EXAMPLE 2 Preparation of Formulations
  • the remaining examples relate to the pesticidal use of the compounds of this invention.
  • a stock solution for the compounds were prepared at 3000 ppm by dissolving 0.3 gram of the compound to be tested in 10 ml of acetone and adding 90 ml of distilled water plus four drops of ethoxylated sorbitan monolaurate, or a simliar suitable wetting agent.
  • this stock solution was used and the specificied dilutions made.
  • a " Figure 8" configuartion of tree tanglefoot was applied to each of two cowpea primary leaves, one from each of two plants in a pot.
  • the circle nearer the stem was designated for the mite ovicide/larvicide test and the circle further from the stem was designated for the mite adulticide test.
  • Groups of adult mites (Tetranychus urticae Koch) were transferred into ovicide circles one day before treatment and the females were allowed to deposit eggs until one hour before treatment when the adults were removed. Plants were sprayed to run off with a 1000 ppm solution diluted from the 3000 ppm stock solution.
  • EXAMPLE 4 Rice Planthopper Foliar Test The stock solution of 3000 ppm was diluted to 1000 ppm. One pot containing approximately 20 Mars variety rice seedlings was treated with each formulation by spraying with a spray atomizer. One day after treatment plants were covered with a tubular cage and twenty adult rice delphacides, Sogatodes orizicola, were transferred into each cage. Five days after transferring, counts were made of the surviving planthoppers in each pot and percent control was estimated.
  • Tobacco Budworm Test The stock solution of 3000 ppm was used for this test. For each compound, 0.2 ml was pipetted onto the surface of each of 5 diet cells, allowed to spread over the surfaces and air dried for two hours. Then a second instar Helicoverpa virescens larva was introduced into each cell. After 14 days, the number of living larvae was determined for each treatment and percent control, corrected by Abbott's formula, was calculated. The results of the testing of tobacco budworms (TB) are given in Tables I and II.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention se rapporte aux composés représentés par la formule (Ia) dans ladite formule Z représente (a), où x est un nombre entier compris entre 0 et 4, n est un nombre entier compris entre 0 et 5 et R a la définition ci-dessous; ou bien (b), où n et un nombre entier compris entre 0 et 5 et R a la définition ci-dessous. R appartient au groupe comprenant: hydrogène; alkyle C1-C4; alcoxy C1-C4; halogène; nitro; phényle; cyano; phénoxy; benzyloxy; benzyle; dialkylamino C1-C4; alkylthio C1-C4; haloalcoxy C1-C4; ou haloalkyle C1-C4; et R1 représente haloalkyle C¿1?-C4 autre que chloroalkyle, ou bien un groupe de la formule (IIa), dans laquelle R?4¿ représente hydrogène, halogène, haloalkyle C¿1?-C4 ou bien haloalcoxy C1-C4; ou encore les sels physiologiquement acceptables de ces éléments, à condition que lorsque x est égal à 0, R?1¿ ne représente pas haloalkyle. Les composés en question ont des propriétés insecticides et acaricides.
PCT/US1995/006270 1995-05-17 1995-05-17 Oxadiazines pesticides WO1996036618A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
EP95920514A EP0825990A1 (fr) 1995-05-17 1995-05-17 Oxadiazines pesticides
PCT/US1995/006270 WO1996036618A1 (fr) 1995-05-17 1995-05-17 Oxadiazines pesticides
BR9510594-8A BR9510594A (pt) 1995-05-17 1995-05-17 Oxadiazinas pesticidas
KR1019970708149A KR100417794B1 (ko) 1995-05-17 1995-05-17 농약용옥사디아진
JP53477896A JP3210676B2 (ja) 1995-05-17 1995-05-17 有害生物駆除性オキサジアジン類
AU25943/95A AU697128B2 (en) 1995-05-17 1995-05-17 Pesticidal oxadiazines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US1995/006270 WO1996036618A1 (fr) 1995-05-17 1995-05-17 Oxadiazines pesticides

Publications (1)

Publication Number Publication Date
WO1996036618A1 true WO1996036618A1 (fr) 1996-11-21

Family

ID=22249137

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1995/006270 WO1996036618A1 (fr) 1995-05-17 1995-05-17 Oxadiazines pesticides

Country Status (6)

Country Link
EP (1) EP0825990A1 (fr)
JP (1) JP3210676B2 (fr)
KR (1) KR100417794B1 (fr)
AU (1) AU697128B2 (fr)
BR (1) BR9510594A (fr)
WO (1) WO1996036618A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998033794A1 (fr) * 1997-01-30 1998-08-06 Uniroyal Chemical Company, Inc. Composes insecticides d'oxadiazines
WO1998038181A1 (fr) * 1997-02-26 1998-09-03 Uniroyal Chemical Company, Inc. Pesticides de thiadiazine
JP3378237B2 (ja) 1998-02-12 2003-02-17 ユニロイヤル ケミカル カンパニー インコーポレイテッド 殺虫性ジヒドロ−オキサジアジン類、−チアジアジン類および−トリアジン類

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3420826A (en) * 1966-09-28 1969-01-07 Dow Chemical Co 2,4,6-(substituted)-1,3,4-oxadiazines and method for their preparation
WO1992011249A1 (fr) * 1990-12-21 1992-07-09 E.I. Du Pont De Nemours And Company Carboxanilides arthropodicides

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3420826A (en) * 1966-09-28 1969-01-07 Dow Chemical Co 2,4,6-(substituted)-1,3,4-oxadiazines and method for their preparation
WO1992011249A1 (fr) * 1990-12-21 1992-07-09 E.I. Du Pont De Nemours And Company Carboxanilides arthropodicides

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
CHEM. PHARM. BULL., vol. 8, pages 543 - 50 *
CHEMICAL ABSTRACTS, vol. 55, no. 11, 29 May 1961, Columbus, Ohio, US; abstract no. 10465c, M. ISHIDATE ET AL.: "Cancerocidal substances. XXIX. 1,1-Bis(2-chloroethyl)hydrazine and its derivatives as tumor-inhibiting agents" *
M.A. DEKEYSER ET AL.: "Insecticidal, miticidal, and ovicidal activity of 5,6-dihydro-4H-1,3,4-oxadiazines", JOURNAL OF ECONOMIC ENTOMOLOGY, vol. 86, no. 5, COLLEGE PARK, MARYLAND US, pages 1339 - 43 *
M.A. DEKEYSER ET AL.: "Synthesis and miticidal and insecticidal activitities of 4-(2-fluoroethyl)-5,6-dihydro-4H-1,3,4- oxadiazines", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 41, no. 8, WASHINGTON DC, US, pages 1329 - 31 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998033794A1 (fr) * 1997-01-30 1998-08-06 Uniroyal Chemical Company, Inc. Composes insecticides d'oxadiazines
KR100711325B1 (ko) * 1997-01-30 2007-04-27 유니로얄 캐미칼 캄파니, 인크. 살충제 옥사디아진 화합물
WO1998038181A1 (fr) * 1997-02-26 1998-09-03 Uniroyal Chemical Company, Inc. Pesticides de thiadiazine
JP3378237B2 (ja) 1998-02-12 2003-02-17 ユニロイヤル ケミカル カンパニー インコーポレイテッド 殺虫性ジヒドロ−オキサジアジン類、−チアジアジン類および−トリアジン類

Also Published As

Publication number Publication date
EP0825990A1 (fr) 1998-03-04
AU2594395A (en) 1996-11-29
KR100417794B1 (ko) 2004-06-04
KR19990014805A (ko) 1999-02-25
BR9510594A (pt) 2002-01-08
JPH10507775A (ja) 1998-07-28
JP3210676B2 (ja) 2001-09-17
AU697128B2 (en) 1998-09-24

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