WO2008144116A1 - Pesticidal diazene oxide carboxylates - Google Patents
Pesticidal diazene oxide carboxylates Download PDFInfo
- Publication number
- WO2008144116A1 WO2008144116A1 PCT/US2008/059239 US2008059239W WO2008144116A1 WO 2008144116 A1 WO2008144116 A1 WO 2008144116A1 US 2008059239 W US2008059239 W US 2008059239W WO 2008144116 A1 WO2008144116 A1 WO 2008144116A1
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- Prior art keywords
- branched
- straight
- chain
- compound
- alkyl
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C291/00—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00
- C07C291/02—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds
- C07C291/08—Azoxy compounds
Definitions
- the present invention relates to certain diazene oxide carboxylate compounds and compositions, that are useful as pesticides.
- the present invention also relates to a method for controlling pests such as mites, by contacting the pests with a pesticidally effective amount of the diazene oxide carboxylate compounds, or by applying the diazene oxide carboxylate compounds to plant foliage susceptible to attack by said pests.
- X is a) phenyl; lower phenylalkoxy; phenoxy; or benzyl; or b) one substituent from group a) and one or more substituents selected from Ci-C 4 alkoxy; halogen; lower alkyl; and lower alkylthio; or c) along with the phenyl to which it is attached, forms a multiple fused ring heterocycle such as dibenzofuranyl;
- Y is H, Ci-C 4 alkanoyl, Ci-C 4 haloalkanoyl, dialkoxyphosphoryl, alkylaminocarbonyl, haloalkylsulfonyl, or CpC 4 alkoxy carbonyl; and
- R is H, Ci-C 6 alkyl, Ci-C 6 alkoxy, C 3 -C 6 cycloalkoxy, haloalkyl, alkoxyalkyl, arylalkoxy, alkenyl, alkylthio, alkoxycarbonyl, alkylamino, heteroaryl, arylalkyl, haloalkoxy, aryloxy, or C 3 -C 6 cycloalkyl; and Z is O or S.
- U. S. Patent 5,376,679 discloses a method of combating a fungus, and/or yeast, and/or bacterium, and/or nematode, which method comprises treating plants subject to attack with a compound of the formula:
- U. S. Patent 5,084,448 discloses a method of combating a fungus, which method comprises treating the fungus with a fungicidally effective amount of a compound of the formula:
- R represents an optionally substituted aryl group
- X represents a hydrogen atom or an amino group or an optionally substituted alkyl, aryl, or thienyl group
- Z represents a hydrogen atom or alkanoyl group
- the present invention relates to a compound having the structural formula:
- R is C 1 -C 6 branched or straight chain alkyl; C 1 -C 4 branched or straight-chain haloalkyl; or C 3 -C 6 cycloalkyl; m is O, 1, or 2;
- X is selected from the group consisting of: C 1 -C 6 branched or straight-chain alkoxy; halogen; C 1 -C 6 branched or straight-chain alkyl; or C 1 -C 6 branched or straight-chain alkylthio; n is 0 or 1 ;
- A is O; CH 2 ; or NR', wherein R' is (C,-C 6 alkyl)carbonyl;
- Y is phenyl; benzyl; thiazolyl; thienyl; pyridyl; or tetrahydrofuranyl, the aromatic ring of each substituent being optionally substituted with one or more of halogen, C]-C 6 branched or straight-chain alkyl, or C 1 -C 6 branched or straight-chain haloalkyl.
- the present invention is also directed to a method for controlling pests such as mites by contacting the pests with a pesticidally effective amount of at least one compound of the structural formula:
- R 2 is C 1 -C 6 branched or straight chain alkyl; Ci-C 4 branched or straight-chain haloalkyl; or C 3 -C 6 cycloalkyl; m is O, 1, or 2; X is selected from the group consisting of: C 1 -C 6 branched or straight-chain alkoxy; halogen; C 1 -C 6 branched or straight-chain alkyl; or C 1 -C 6 branched or straight-chain alkylthio; n is 0 or 1 ;
- A is O; CH 2 ; or NR', wherein R' is (C 1 -C 6 alkyl)carbonyl; Y is phenyl; benzyl; thiazolyl; thienyl; pyridyl; or tetrahydrofuranyl, the aromatic ring of each substituent being optionally substituted with one or more of halogen, C 1 -C 6 branched or straight-chain alkyl, or C 1 -C 6 branched or straight-chain haloalkyl.
- the present invention is directed to a composition
- a composition comprising:
- R is C 1 -C 6 branched or straight chain alkyl; C 1 -C 4 branched or straight-chain haloalkyl; or C 3 -C 6 cycloalkyl; m is 0, 1, or 2;
- X is selected from the group consisting of: CpC 6 branched or straight-chain alkoxy; halogen; C 1 -C 6 branched or straight-chain alkyl; or C 1 -C 6 branched or straight-chain alkylthio; n is O or l;
- A is O; CH 2 ; or NR', wherein R' is (C 1 -C 6 alkyl)carbonyl; Y is phenyl; benzyl; thiazolyl; thienyl; pyridyl; or tetrahydrofuranyl, the aromatic ring of each substituent being optionally substituted with one or more of halogen, C 1 -C 6 branched or straight-chain alkyl, or Ci-C 6 branched or straight-chain haloalkyl; and (B) a suitable carrier.
- the present invention is directed to compounds of the structural formula:
- R 2 is Ci-C 6 branched or straight chain alkyl; Ci-C 4 branched or straight-chain haloalkyl; or C 3 -C 6 cycloalkyl; m is 0, 1, or 2; X is selected from the group consisting of: C)-C 6 branched or straight-chain alkoxy; halogen; C]-C 6 branched or straight-chain alkyl; or Ci-C 6 branched or straight-chain alkylthio; n is 0 or 1;
- A is O; CH 2 ; or NR', wherein R' is (Cj-C 6 alkyl)carbonyl;
- Y is phenyl; benzyl; thiazolyl; thienyl; pyridyl; or tetrahydrofuranyl, the aromatic ring of each substituent being optionally substituted with one or more of halogen, Ci-C 6 branched or straight-chain alkyl, or Ci-C 6 branched or straight-chain haloalkyl; use of the compounds of Formula I as pesticides, e.g., insecticides, acaricides, and nematicides, and compositions comprising the compounds of Formula I.
- pesticides e.g., insecticides, acaricides, and nematicides
- X is Ci-C 6 branched or straight-chain alkoxy
- Y is phenyl
- R 2 is Ci-C 6 branched or straight-chain alkyl.
- the compounds of Formula I are preferably useful as acaricides for the control of mites and other acarids.
- the present invention more preferably relates to diazene oxide carboxylate compounds of the structural formula:
- R 1 and R 2 are each, independently, C )-6 branched or straight-chain alkyl; use of the diazene oxide carboxylate compounds as pesticides, e.g., insecticides, acaricides, and nematicides, and compositions comprising the diazene oxide carboxylate compounds.
- R 1 and R 2 are each, independently, methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tert-butyl, pentyl, isopentyl, hexyl, or isohexyl.
- R 1 and R 2 are each, independently, lower alkyl of from one to four carbon atoms. Most preferably, R 1 is methyl or ethyl, and R 2 is methyl, ethyl, or isopropyl.
- the compounds of the present invention can be prepared by reacting a suitably substituted compound of formula III:
- oxidizing agent such as meta-chloroperbenzoic acid or other "peroxy" reagent
- a suitable inert organic solvent for example a halogenated hydrocarbon, such as dichloromethane, at a temperature in the range, suitably, -20° to 60° C.
- halogenated hydrocarbon such as dichloromethane
- compositions of this invention comprise (a) a compound having a structure within that of formulas I or II above, and (b) a suitable carrier.
- suitable carriers may be solid or liquid in nature.
- the compositions are preferably pesticidally active and more preferably, acaricidally active.
- Suitable liquid carriers maybe comprised of water, alcohols, ketones, phenols, toluene and xylenes.
- additives conventionally employed in the art may be utilized such as, for example, one or more surface active agents and/or inert diluents, to facilitate handling an application of the resulting pesticide composition.
- 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 applicable directly to the loci to be treated.
- powdered solid carriers such as mineral silicates, e.g., mica, talc, pyrophyllite and clays
- 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 suitably prepared using a granular or pellitized form of carrier such as granular clays, vermiculite, charcoal or corn cobs.
- the pesticidal compounds may be applied in liquids 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, for example, water.
- 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 include those known in the art, such as those disclosed in U.S.
- Patent 2,547,724 (columns 3 and 4).
- the compounds of the invention may be mixed with such surface-active dispersing agents, with or without an organic solvent, as concentrates for the subsequent addition of water to yield aqueous suspensions of the compounds at desired concentration levels.
- 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, where plants constitute the loci of treatment, 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. To combat pests, sprays of the compounds may be applied 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.
- 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 and compositions of this invention are particularly useful as acaricides for foliar application.
- the organic phase was dried with sodium sulfate and evaporated to give the product as a brown-orange solid (9.78 g).
- the product was purified using silica gel chromatography (1 :5 ethyl acetate : hexane). Evaporation of the desired fractions gave purified product as an orange solid (6.19 g), with melting point 102-106 °C.
- ovicide/larvicide circles were examined for hatched eggs and living immature mites. The percent control was estimated based on the number of eggs hatching and immature mites surviving on the check plants.
- O ovicidal
- L larvicidal
- MI mite adulticide
- MIOVL ovicide/larvicide
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE602008004238T DE602008004238D1 (en) | 2007-05-16 | 2008-04-03 | PESTICIDE DIAMIDE OXIC CARBOXYLATE |
AP2009005058A AP2009005058A0 (en) | 2007-05-16 | 2008-04-03 | Pesticidal diazene oxide carboxylates |
CA002684944A CA2684944A1 (en) | 2007-05-16 | 2008-04-03 | Pesticidal diazene oxide carboxylates |
EP08745008A EP2146955B1 (en) | 2007-05-16 | 2008-04-03 | Pesticidal diazene oxide carboxylates |
CN200880021147.1A CN101679227B (en) | 2007-05-16 | 2008-04-03 | Pesticidal diazene oxide carboxylates |
AT08745008T ATE493384T1 (en) | 2007-05-16 | 2008-04-03 | PESTICIDES DIAZENE OXIDE CARBOXYLATES |
DK08745008.6T DK2146955T3 (en) | 2007-05-16 | 2008-04-03 | Pesticide diazene oxide carboxylates |
AU2008254388A AU2008254388B2 (en) | 2007-05-16 | 2008-04-03 | Pesticidal diazene oxide carboxylates |
JP2010508471A JP5189642B2 (en) | 2007-05-16 | 2008-04-03 | Diazene oxide carboxylate for pesticides |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/804,282 US7399757B1 (en) | 2007-05-16 | 2007-05-16 | Pesticidal diazene oxide carboxylates |
US11/804,282 | 2007-05-16 | ||
US12/070,833 | 2008-02-20 | ||
US12/070,833 US7511029B2 (en) | 2007-05-16 | 2008-02-20 | Pesticidal diazene oxide carboxylates |
Publications (1)
Publication Number | Publication Date |
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WO2008144116A1 true WO2008144116A1 (en) | 2008-11-27 |
Family
ID=39758770
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2008/059239 WO2008144116A1 (en) | 2007-05-16 | 2008-04-03 | Pesticidal diazene oxide carboxylates |
Country Status (11)
Country | Link |
---|---|
US (1) | US7511029B2 (en) |
EP (1) | EP2146955B1 (en) |
JP (1) | JP5189642B2 (en) |
CN (1) | CN101679227B (en) |
AP (1) | AP2009005058A0 (en) |
AT (1) | ATE493384T1 (en) |
AU (1) | AU2008254388B2 (en) |
CA (1) | CA2684944A1 (en) |
DE (1) | DE602008004238D1 (en) |
DK (1) | DK2146955T3 (en) |
WO (1) | WO2008144116A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010132509A3 (en) * | 2009-05-11 | 2011-09-15 | Agraquest, Inc. | Compounds derived from muscodor fungi |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20130165880A1 (en) | 2010-09-17 | 2013-06-27 | David T. Amos | Antimicrobial disposable absorbent articles |
CN105028441B (en) * | 2015-02-12 | 2017-06-09 | 四川利尔作物科学有限公司 | Insecticide acaricide composition and its application |
CN115197103A (en) * | 2022-06-01 | 2022-10-18 | 浙江农林大学 | Azo compounds or azoxy compounds, their salts suitable for agriculture and forestry, their compositions, their preparation and use |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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US4550121A (en) * | 1984-08-22 | 1985-10-29 | Shell Oil Company | (2-Substituted-2,3-dihydrobenzo-furan-7-yl)diazenecarboxylic acid esters and miticidal method |
US4558040A (en) * | 1984-12-03 | 1985-12-10 | Shell Oil Company | Miticidal (2-alkyl-3,4-dihydro-2H-1-benzopyran-8-yl)-diazenecarboxylic acid esters |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3980522A (en) * | 1973-09-14 | 1976-09-14 | Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai | Production of a new antibiotic, calvatic acid |
GB8827850D0 (en) * | 1988-11-29 | 1988-12-29 | Shell Int Research | Biocidal compounds |
GB8917850D0 (en) | 1989-08-04 | 1989-09-20 | Shell Int Research | Biocidal compounds |
RU2109730C1 (en) | 1991-11-22 | 1998-04-27 | Юнироял Кемикал Компани, Инк. | Phenylhydrazine derivatives, method of controlling pests and insectoacaricidonematocidal composition |
WO1993010083A1 (en) * | 1991-11-22 | 1993-05-27 | Uniroyal Chemical Company, Inc. | Insecticidal phenylhydrazine derivatives |
US5567723A (en) * | 1995-07-05 | 1996-10-22 | Uniroyal Chemical Company, Inc. | Miticidal hydrazine compounds and their intermediates |
DE19601626A1 (en) * | 1996-01-18 | 1997-07-24 | Bayer Ag | Substituted N-aryl nitrogen heterocycles |
US6093843A (en) * | 1999-10-06 | 2000-07-25 | Uniroyal Chemical Company, Inc. | 4-hydroxybiphenyl hydrazide derivatives |
US6706895B1 (en) * | 2002-11-14 | 2004-03-16 | Uniroyal Chemical Company, Inc. | 4-methoxybiphenyl hydrazone derivatives |
US7592374B2 (en) * | 2005-03-03 | 2009-09-22 | Crompton Corporation | Insecticidal nitromethylene compounds |
US7399757B1 (en) * | 2007-05-16 | 2008-07-15 | Chemtura Corporation | Pesticidal diazene oxide carboxylates |
-
2008
- 2008-02-20 US US12/070,833 patent/US7511029B2/en active Active
- 2008-04-03 WO PCT/US2008/059239 patent/WO2008144116A1/en active Application Filing
- 2008-04-03 AT AT08745008T patent/ATE493384T1/en active
- 2008-04-03 CN CN200880021147.1A patent/CN101679227B/en not_active Expired - Fee Related
- 2008-04-03 DK DK08745008.6T patent/DK2146955T3/en active
- 2008-04-03 DE DE602008004238T patent/DE602008004238D1/en active Active
- 2008-04-03 AU AU2008254388A patent/AU2008254388B2/en active Active
- 2008-04-03 JP JP2010508471A patent/JP5189642B2/en active Active
- 2008-04-03 AP AP2009005058A patent/AP2009005058A0/en unknown
- 2008-04-03 CA CA002684944A patent/CA2684944A1/en not_active Abandoned
- 2008-04-03 EP EP08745008A patent/EP2146955B1/en active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4550121A (en) * | 1984-08-22 | 1985-10-29 | Shell Oil Company | (2-Substituted-2,3-dihydrobenzo-furan-7-yl)diazenecarboxylic acid esters and miticidal method |
US4558040A (en) * | 1984-12-03 | 1985-12-10 | Shell Oil Company | Miticidal (2-alkyl-3,4-dihydro-2H-1-benzopyran-8-yl)-diazenecarboxylic acid esters |
Non-Patent Citations (1)
Title |
---|
MORTARINI V., CALVINO R.: "Antifungal Activity of Methyl and Ethyl Phenyldiazenecarboxylate 2-Oxide Derivatives", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, vol. 15, no. 5, 1980, pages 475 - 478, XP002497063 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010132509A3 (en) * | 2009-05-11 | 2011-09-15 | Agraquest, Inc. | Compounds derived from muscodor fungi |
Also Published As
Publication number | Publication date |
---|---|
AP2009005058A0 (en) | 2009-12-31 |
CN101679227A (en) | 2010-03-24 |
US7511029B2 (en) | 2009-03-31 |
EP2146955A1 (en) | 2010-01-27 |
EP2146955B1 (en) | 2010-12-29 |
ATE493384T1 (en) | 2011-01-15 |
AU2008254388A1 (en) | 2008-11-27 |
DK2146955T3 (en) | 2011-03-28 |
DE602008004238D1 (en) | 2011-02-10 |
JP2010527362A (en) | 2010-08-12 |
CN101679227B (en) | 2013-06-19 |
CA2684944A1 (en) | 2008-11-27 |
US20080287535A1 (en) | 2008-11-20 |
JP5189642B2 (en) | 2013-04-24 |
AU2008254388B2 (en) | 2013-05-02 |
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