WO1996036618A1 - Pesticidal oxadiazines - Google Patents
Pesticidal oxadiazines Download PDFInfo
- 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
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.
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- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (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
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1019970708149A KR100417794B1 (en) | 1995-05-17 | 1995-05-17 | Pesticide oxadiazine |
JP53477896A JP3210676B2 (en) | 1995-05-17 | 1995-05-17 | Pest control oxadiazines |
EP95920514A EP0825990A1 (en) | 1995-05-17 | 1995-05-17 | Pesticidal oxadiazines |
PCT/US1995/006270 WO1996036618A1 (en) | 1995-05-17 | 1995-05-17 | Pesticidal oxadiazines |
BR9510594-8A BR9510594A (en) | 1995-05-17 | 1995-05-17 | Pesticide oxadiazines |
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 (en) | 1995-05-17 | 1995-05-17 | Pesticidal oxadiazines |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1996036618A1 true WO1996036618A1 (en) | 1996-11-21 |
Family
ID=22249137
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1995/006270 WO1996036618A1 (en) | 1995-05-17 | 1995-05-17 | Pesticidal oxadiazines |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP0825990A1 (en) |
JP (1) | JP3210676B2 (en) |
KR (1) | KR100417794B1 (en) |
AU (1) | AU697128B2 (en) |
BR (1) | BR9510594A (en) |
WO (1) | WO1996036618A1 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1998033794A1 (en) * | 1997-01-30 | 1998-08-06 | Uniroyal Chemical Company, Inc. | Insecticidal oxadiazine compounds |
WO1998038181A1 (en) * | 1997-02-26 | 1998-09-03 | Uniroyal Chemical Company, Inc. | Pesticidal thiadiazines |
JP3378237B2 (en) | 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 | Insecticidal dihydro-oxadiazines, -thiadiazines and -triazines |
Citations (2)
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 (en) * | 1990-12-21 | 1992-07-09 | E.I. Du Pont De Nemours And Company | Arthropodicidal carboxanilides |
-
1995
- 1995-05-17 BR BR9510594-8A patent/BR9510594A/en not_active IP Right Cessation
- 1995-05-17 WO PCT/US1995/006270 patent/WO1996036618A1/en not_active Application Discontinuation
- 1995-05-17 JP JP53477896A patent/JP3210676B2/en not_active Expired - Fee Related
- 1995-05-17 KR KR1019970708149A patent/KR100417794B1/en not_active Expired - Fee Related
- 1995-05-17 AU AU25943/95A patent/AU697128B2/en not_active Ceased
- 1995-05-17 EP EP95920514A patent/EP0825990A1/en not_active Withdrawn
Patent Citations (2)
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 (en) * | 1990-12-21 | 1992-07-09 | E.I. Du Pont De Nemours And Company | Arthropodicidal carboxanilides |
Non-Patent Citations (4)
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)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1998033794A1 (en) * | 1997-01-30 | 1998-08-06 | Uniroyal Chemical Company, Inc. | Insecticidal oxadiazine compounds |
KR100711325B1 (en) * | 1997-01-30 | 2007-04-27 | 유니로얄 캐미칼 캄파니, 인크. | Insecticide Oxadiazine Compounds |
WO1998038181A1 (en) * | 1997-02-26 | 1998-09-03 | Uniroyal Chemical Company, Inc. | Pesticidal thiadiazines |
JP3378237B2 (en) | 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 | Insecticidal dihydro-oxadiazines, -thiadiazines and -triazines |
Also Published As
Publication number | Publication date |
---|---|
AU2594395A (en) | 1996-11-29 |
KR100417794B1 (en) | 2004-06-04 |
EP0825990A1 (en) | 1998-03-04 |
JP3210676B2 (en) | 2001-09-17 |
BR9510594A (en) | 2002-01-08 |
KR19990014805A (en) | 1999-02-25 |
JPH10507775A (en) | 1998-07-28 |
AU697128B2 (en) | 1998-09-24 |
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