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
  • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring

Definitions

• the invention relates generally to insecticides and more particularly to a topical insecticide, such as one suitable to use on house pets such as cats and dogs.
• Topical applications can be desirable, in that many insecticides are acceptably safe when used topically, but not when used internally.
• insecticide should be safe for human contact. It should also not lead to staining of furniture, carpeting and the like.
• a topical insecticide which can be safe to use and avoids many common deleterious side effects of conventional topical insecticides.
• the active ingredient of the insecticide formulation is an amine derivative, having a nitro-methylene group, a nitroamino group or a cyanoamino group, which can be formulated to have low toxicity and excellent insecticidal activity. Active ingredients of insecticides and their method of formation in accordance with the preferred embodiments of the invention are discussed in U.S. Patent No. 5,532,365 and 5,434,181, the contents of which are incorporated herein by reference.
• One particularly suitable insecticide is l- ⁇ (tetrahydro-3-furanyl)methyl ⁇ -2-nitro-3-methylguanidine (dinotefuran). Dinotefuran is an aldulticide that will kill adult fleas.
• the active portion of the insecticide formulation comprises (tetrahydro-3-furanyl)methylamine derivatives of following formula (1).
• Active ingredients and insecticides in accordance with preferred embodiments of the invention are generally available as crystals and solids. Therefore, they need to be dissolved or otherwise put into a liquid form for use as topical spot products on animals. Topical spot products are more advantageous if the amount of liquid applied can be minimized. This must be balanced with the need for appropriate dosage to achieve the desired insecticidal effect. Therefore, it is desirable to use a solvent that will allow the solubilization of a high concentration of insecticide.
• Phenyl methanol is an alcohol, also known as benzyl alcohol, and is a liquid, somewhat soluble in water. It is routinely used in perfumes, flavors, photographi-c developers, dyes, films and inks and has other uses. It was surprisingly discovered that a relatively high concentration of the insecticide can be solubilized in phenyl methanol.
• the compound is dissolved in solvent to a concentration range of 2 - 20%, more preferably 4 - 17% and most preferably about 8 to 14%, with 12.5% as a preferred example. All percentages, unless otherwise evident, are on a weight basis.
• the preferred solvent component comprises a mixture comprising water, ethyl lactate and ethanol, wherein the final concentration of ethyl lactate ranges from 5 - 20% and the final concentration of ethanol ranges from 30 - 45%, more preferably 7 - 15% ethyl lactate and 35 - 43% ethanol and most preferable a final concentration of 10% ethyl lactate and 40% ethanol.
• the remainder can be water.
• Isopropanol can also be added to ethanol to improve solubility.
• novel (tetrahydro-3-furanyl)methylamine derivatives of the formula (1) have an excellent insecticidal activity even in the absence of a pyridylmethyl group or a thiazolylmethyl group in their molecular structure.
• X ls X 2 , X 3 , X 4 , X 5 , X 6 and X 7 represent each a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms
• Ri represents a hydrogen atom, an alkyl group having from 1 to 5 carbon atoms, an alkenyl group having 3 carbon atoms, a benzyl group, an alkoxyalkyl group having from 2 to 4 carbon atoms (in its whole group), an alkyloxycarbonyl group having from 1 to 3 carbon atoms, a phenoxy carbonyl group, an alkylcarbonyl group having from 1 to 6 carbon atoms, an alkenylcarbonyl group having from 2 to 3 carbon atoms, a cycloalkylcarbonyl group having from 3 to 6 carbon atoms, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a be
• Xj, X 2 , X 3 , X , X 5 , X 6 and X 7 represent each a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms;
• R 10 represents an alkyl group having from 1 to 5 carbon atoms or a benzyl group; and
• R ⁇ represents an alkyl group having from 1 to 5 carbon atoms or a benzyl group.
• novel (tetrahydro-3-furanyl)methylamine derivatives of the formula (1) and formula (2) according to the invention are excellent compounds having a high insecticidal power and broad insecticidal spectrum. Further, agricultural chemicals containing the novel (tetrahydro- 3- furanyl)methylamine derivatives of the formula (1) and (2) according to the invention have outstanding characteristics as insecticides and hence are useful.
• alkyl group for X ls X 2 , X 3 , X 4 , X 5 , X 6 and X 7 in the above formulae (1) and (2) include a methyl group, an ethyl group, an n-propyl group, an iso- propyl group, a tert-butyl group, and the like, preferably a methyl group.
• alkyl group for R t include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n- butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, and the like.
• alkenyl group for Ri include a 1-propenyl group, a 2- propenyl group, and the like.
• alkoxyalkyl group for include a methoxymethyl group, an ethoxymethyl group, an n-propoxymethyl group, an iso-propoxymethyl group, a methoxyethyl group, an ethoxyethyl group, and the like.
• alkyloxycarbonyl group for R ⁇ include a methyloxycarbonyl group, an ethyloxycarbonyl group, an n-propyloxycarbonyl group, an iso- propyloxycarbonyl group, and the like.
• alkylcarbonyl group for include a methylcarbonyl group, an ethylcarbonyl group, an n-propylcarbonyl group, an iso-propylcarbonyl group, an n- butylcarbonyl group, an iso-butylcarbonyl group, a sec-butylcarbonyl group, a tert-butylcarbonyl group, an n-pentylcarbonyl group, an n-hexylcarbonyl group, and the like.
• alkenylcarbonyl group for Ri include a vinylcarbonyl group, a 1-methylvinylcarbonyl group, and the like.
• cycloalkylcarbonyl group for R examples include a cyclopropylcarbonyl group, a cyclobutylcarbonyl group, a cyclopentylcarbonyl group, a cyclohexylcarbonyl group, and the like.
• benzoyl group substituted by alkyl group(s) for Ri include a 2-methylbenzoyl group, a 3-methylbenzoyl group, a 4-methylbenzoyl group, a 4-tert- butylbenzoyl group, and the like.
• benzoyl group substituted by halogen atom(s) for R ⁇ include a 2-chlorobenzoyl group, a 3-chlorobenzoyl group, a 4-chlorobenzoyl group, a 3,4- dichloro-benzoyl group, a 4- fluorobenzoyl group, and the like.
• R can take various substituents as described above, it is preferably a hydrogen atom, an alkylcarbonyl group having from 1 to 4 carbon atoms or a cyclopropylcarbonyl group.
• alkylamino group for R 2 examples include a methylamino group, an ethylamino group, an n-propyl-amino group, an iso-propylamino group, an n-butylamino group, an iso-butylamino group, a sec-butylamino group, a tert-butylamino group, an n- pentylamino group, and the like, preferably a methylamino group.
• di-substituted alkylamino group for R 2 include a dimethylamino group, a diethylamino group, an N-methyl-N-ethylamino group, anN-methyl-N- n-propylamino group, an N-methyl-N-n-butylamino group, and the like, preferably a dimethylamino group.
• alkenylamino group for R 2 examples include a 1-propenylamino group, a 2-propenylamino group, and the like.
• alkynylamino group for R 2 examples include a propargylamino group, and the like.
• alkoxyalkylamino group for R 2 include a methoxymethylamino group, an ethoxymethylamino group, an n-propoxymethylamino group, an iso-propoxymethylamino group, a methoxyethylamino group, an ethoxyethylamino group, and the like.
• alkyloxycarbonyl group denoted by Y ⁇ for R 2 include a methyloxycarbonyl group, an ethyloxy-carbonyl group, an n-propyloxycarbonyl group, an iso- propyloxy-carbonyl group, and the like.
• alkylcarbonyl group denoted by Y for R 2 include a methylcarbonyl group, an ethylcarbonyl group, an n-propylcarbonyl group, an iso- propylcarbonyl group, an n-butylcarbonyl group, an isobutylcarbonyl group, a sec-butylcarbonyl group, a tertbutylcarbonyl group, an n-pentylcarbonyl group, an n-hexylcarbonyl group, and the like, preferably a methylcarbonyl group, an ethylcarbonyl group, an n-propylcarbonyl group, an iso-propylcarbonyl group, an n-butylcarbonyl group, an iso-butylcarbonyl group, a sec-butylcarbonyl group and a tert-butylcarbonyl group.
• alkenyl ethylcarbonyl group, an n
• cycloalkylcarbonyl group denoted by Yi for R 2 include a cyclopropylcarbonyl group, a cyclobutylcarbonyl group, a cyclopentylcarbonyl group, a cyclo- hexylcarbonyl group, and the like, preferably a cyclopropyl-carbonyl group.
• Y ⁇ for R 2 include a 2-methylbenzoyl group, a 3-methylbenzoyl group, a 4-methylbenzoyl group, a 4-tert-butylbenzoyl group, and the like.
• benzoyl group substituted by halogen atom(s) denoted by Y ⁇ for R 2 include a 2-chlorobenzoyl group, a 3-chlorobenzoyl group, a 4-chlorobenzoyl group, a 3,4-dichlorobenzoyl group, a 4-fluoro benzoyl group, and the like.
• alkyl group denoted by Y 2 for R 2 include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, and the like, preferably a methyl group.
• the formulation should be stable for one month at 130° F, 110°F, 40° F, room temperature and 0°F. This helps ensure that the formulation remains stable under the conditions that it could meet in commerce. (c) Safe to use on the animal - particularly non-irritating since the product is applied to the skin. Also safe if ingested by the animal; ingestion can occur when cats groom themselves.
• the solvent comprises phenyl methanol or a combination of ethyl lactate and ethanol
• the active compound is dissolved in solvent to a concentration range of 2 - 20%, more preferably 4 - 11% and most preferably about 8 to 14%, with 12.5% as a preferred example. All percentages, unless otherwise evident, are on a weight basis.
• the preferred solvent component comprises a mixture comprising water, ethyl lactate and ethanol, wherein the final concentration of ethyl lactate ranges from 5 - 20% and the final concentration of ethanol ranges from 30 - 45%, more preferably 7 - 15% ethyl lactate and 35 - 43% ethanol and most preferable a final concentration of 10% ethyl lactate and 40% ethanol.
• the remainder can be water.
• Isopropanol can also be added to ethanol to improve solubility.
• the preferred solvent component comprises a mixture comprising water and ethanol at a concentration range of 50 - 80% ethanol, more preferably 65 - 75% ethanol and most preferably about 69-71% ethanol, with a preferred example 70% ethanol.
• the remainder can be water.
• the insecticide formulation can include various additions to the ethanol/water combination.
• the preferred solvent component comprises a mixture comprising water, ethanol and isopropanol, wherein the final concentration of total alcohol range from 50 - 80% alcohol, more preferably 65 - 75% alcohol and most preferably about 69-11% alcohol, with a preferred example 70% alcohol. The remainder can be water.
• the concentration of ethanol and isopropanol are 25 - 45% ethanol, 25 - 45% isopropanol, more preferably 30 - 40% ethanol, 30 - 40% isopropanol and most preferably 35% ethanol and 35% isopropanol.
• the solvent comprises a mixture comprising dipropyleneglycol monomethyl ether (DPM) and water at a concentration range of about 30 - 70%) DPM, more preferably about 45 - 55% DPM and most preferably about 50% DPM/50% water mixture.
• the preferred solvent is a mixture comprising water, ethanol and DPM at a concentration range of 25 - 40% ethanol, 25 - 40%
• DPM more preferably 30 - 35% ethanol, 30 - 35% DPM and most preferably equal volumes of each component (i.e., 33% ethanol, 33% DPM and 33% water).
• ingredients or compounds recited in the singular are intended to include compatible mixtures of such ingredients wherever the sense permits.

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• 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)
• Furan Compounds (AREA)

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• 2002
  • 2002-09-12 US US10/242,550 patent/US6588374B1/en not_active Expired - Lifetime
• 2003
  • 2003-09-11 AU AU2003266161A patent/AU2003266161A1/en not_active Abandoned
  • 2003-09-11 WO PCT/US2003/028943 patent/WO2004023872A2/en not_active Ceased
  • 2003-09-11 CA CA002498181A patent/CA2498181A1/en not_active Abandoned
  • 2003-09-11 EP EP03795707A patent/EP1536681A4/en not_active Withdrawn
  • 2003-09-11 MX MXPA05002788A patent/MXPA05002788A/es active IP Right Grant
  • 2003-09-11 JP JP2004536344A patent/JP2005539064A/ja active Pending

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