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EP0717591A4 - Composition insecticide - Google Patents

Composition insecticide

Info

Publication number
EP0717591A4
EP0717591A4 EP94926721A EP94926721A EP0717591A4 EP 0717591 A4 EP0717591 A4 EP 0717591A4 EP 94926721 A EP94926721 A EP 94926721A EP 94926721 A EP94926721 A EP 94926721A EP 0717591 A4 EP0717591 A4 EP 0717591A4
Authority
EP
European Patent Office
Prior art keywords
alkyl
alkoxy
halo
group
substituted
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Withdrawn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
EP94926721A
Other languages
German (de)
English (en)
Other versions
EP0717591A1 (fr
Inventor
Ian Maxwell Russell
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.)
Commonwealth Scientific and Industrial Research Organization CSIRO
Original Assignee
Commonwealth Scientific and Industrial Research Organization CSIRO
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 Commonwealth Scientific and Industrial Research Organization CSIRO filed Critical Commonwealth Scientific and Industrial Research Organization CSIRO
Publication of EP0717591A1 publication Critical patent/EP0717591A1/fr
Publication of EP0717591A4 publication Critical patent/EP0717591A4/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
    • D06M16/006—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic with wool-protecting agents; with anti-moth agents
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/28—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group; Thio analogues thereof

Definitions

  • the present invention is concerned with the use of insecticidally active compounds for the treatment of wool or wool-containing materials.
  • the invention is also concerned with insecticidally active compositions which are capable of protecting wool or wool-containing materials against insect attack.
  • Permethrin is currently the main commercial mothproofing chemical. In the UK, aquatic discharges of permethrin will be restricted from the start of 1993. This decision effectively stops the dyebath application of permethrin, as small amounts of insect resist chemical will always be discharged with the exhausted liquors even under the best industrial conditions. Although permethrin can still be used for treatment of wool, it must be applied in totally contained systems that do not give rise to environmental residues.
  • Dyebath application is the simplest, cheapest and most universal point in the wool processing sequence to apply mothproofing agents; no specialised equipment is needed, and the high temperature application provides a treatment with optimum fastness properties. If insect-resist agents are to be applied to wool in the dyebath, special compounds with very low hazard to aquatic organisms of all kinds must be used. Disclosure of the Invention
  • a further object of this invention is to provide a mothproofing treatment which is more environmentally acceptable that the prior art treatments referred to above.
  • substituents A, B, X, X', R 1 , R 2 , R 3 and R 4 are as defined in above-mentioned Australian application no. 76287/87, that is, wherein X and X' are the same or different O.S or NR;
  • R 1 is hydrogen; (C r C 6 ) alkyl; (C r C 6 ) alkoxy-(C r C 6 ) alkoxy-(C r C 6 ) alkyl having independently the stated number of carbon atoms in each alkyl group; (C r C 6 ) alkylthio- (C-C 6 ) alkyl having independently the stated number of carbon atoms in each alkyl group; (C 2 .-C 6 ) alkenyi; (C 2 -C 6 ) alkynyl; or phen-(C.,-C 4 ) alkyl where the phenyl ring is unsubstituted or substituted with one to three of the same or different halo, cyano, nitro, hydroxy, (C,-C 4 ) alkyl, halo-(C,-C 4 ) alkyl (C r C 4 )-alkoxy, halo-(C,-C 4 ) alkoxy, carb
  • R 2 and R 3 are the same or different hydrogen or (C C 4 ) alkyl;
  • R 4 is (C C 4 ) alkyl substituted with 1 to 4 fluoro; straight chain (C 2 -C 4 ) alkenyi; carboxyl; (C
  • a and B are the same or different unsubstituted or substituted naphthytyl where the substituents can be from one to three of the same or different halo; nitro; (C C 4 )- alkoxy; (C,-C 4 ) alkyl or NZZ';
  • the present invention provides a method of mothproofing wool or a wool- containing product said method including treating said wool or wool-containing product with an effective amount of a compound according to the formula (I)
  • the treatment compound has relatively low water solubility.
  • the water solubility of the treatment compound is less than 1 mg/l, although compounds with higher solubility may be used.
  • the treatment compound is a compound having the following formula:
  • the treatment compound may be of the formula:
  • the treatment compound may be applied at a level of about 0.001 % - 0.5%.
  • the treatment compound may be applied in a dyebath, either to the whole of the wool or wool blend lot, or by overtreatment of a small fraction with subsequent blending with untreated wool.
  • the treatment compound may be applied by continuous padding, scouring application, continuous application in chemical setting or tape scouring, foam application, encapsulation in particles, centrifuge, or minibowl.
  • the wool product may be subjected to steaming or heating following application of the treatment compound.
  • the treatment compound may be applied as a solution in an organic solvent, for example, ethanol.
  • the treatment compound may also be applied as a suspension of the micro- ground compound, a self-emulsifiable concentrate or other water-based formulation as application vehicles.
  • Compound (IV) which is relatively hydrophobic, has a specific activity to lepidoptera larvae and with water solubility below 1 mg/l, is more environmentally acceptable than permethrin.
  • the treatment compounds of the present invention have very high insecticidal activity against all five of our test strains of clothes moths: common clothes moth (Tineola bisselliella), dieldrin resistant and dieldrin susceptible strains; casebearing clothes moth (Tinea translucens), susceptible, dieldrin resistant and pyrethroid resistant strain.
  • Insect-resist activity is required to persist through the life-time of a wool product.
  • Application of 5-10 fold excess of active ingredient above the minimum active level may be used to ensure protection even after 80%-90% losses through volatility, exposure to light, and cleaning (washing, shampooing and dry-cleaning).
  • compound (IV) has more than adequate fastness for a commercial insect-resist treatment.
  • compound (IV) has similar washing performance to conventional synthetic pyrethroid (permethrin or cycloprothrin) mothproofing compounds and better dry cleaning resistance and light fastness.
  • the present invention provides, in a second aspect, a method of treating a wool or wool-containing product the method including treating the wool or wool-containing product with a compound according to formula (I) together with an agent which has an activity against beetles.
  • a treatment compound of the invention may have a synergistic effect on the activity of an agent having activity against beetles.
  • the agent active against beetles may be a compound selected from synthetic pyrethroids, repellants and disinfectant materials, and other specialty wool insect resist agents of the aryl ureido and amide class.
  • the agent active against beetles may be permethrin or bifenthrin, as examples of pyrethroids with a high activity against beetles.
  • the agent may be selected from hexahydropyrimidine derivative (HHP): N-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-6- hydroxy-1 ,3-dimethyl-2,4-dioxo-5-pyrimidinecarboxamide, flucofuron: N,N'-bis[4-chloro-3- (trifluoromethyl)phenyl] urea, butyl ester of 4-hydroxy benzoic acid, and sulcofuron:5- chloro-2-(4-chloro-2-(3,4-chlorophenyl)) phenoxyureido benzene sulfonate (as alkali salt, for example the sodium salt).
  • the agent having activity against beetles may be a nitromethylene of formula
  • the agent having activity against beetles is applied at a level of about 0.0001% to 0.1%.
  • the present invention provides a treatement composition suitable for use in the method of the present invention said composition including one or more compounds of formula (I) to (IV) and optionally including one or more compounds active against beetles.
  • Figure 1 shows the Freundlich adsorption isotherm for compound (IV) on wool at 100°C
  • Figure 2 is a graph showing light fastness of woolen fabrics treated with compound (IV);
  • Figure 3 is a graph showing the handwashing characteristics of fabrics treated with compound (IV).
  • Figure 4 is a graph showing the effect of dry cleaning on wool treated with compound
  • Compounds according to formula (III) may be prepared by benzoylation of a t-butyl hydrazine under Schotten-Baumann conditions. The product was recrystallised from methanol-ether; purity and structure were confirmed by nmr.
  • Wool was treated with the insecticide in an Ahiba dyeing apparatus at 100°C for 30 minutes as described in AS2001.
  • the insecticide was applied at the start of the dyeing cycle either as an ethanol solution, or as a micro-ground suspension (Compound (IV) 2F 23%ai or Compound (IV) FL 20%ai).
  • Fabrics were rinsed in cold water then air dried after application. Generally 20g of wool was treated in 500cm 3 of water.
  • Hot dyebath liquors (75ml) were taken from the dyebath and diluted to 100ml with methanol. The resulting solutions were used directly for HPLC analysis. Wash and Dry Clean Fastness testing
  • Permethrin was applied to wool from boiling dyebaths.
  • the treatment compounds caused 100% kill in the 14 day test. At levels around 0.00025%, approximately 50% of the larvae were still alive, but appeared abnormal. Even at levels of 0.0001%, larval feeding was only 30-40% of control wool. At high level (0.1%), the Tinea larvae crawled from their cases before dying, usually an indicator of distress.
  • Insect-resist activity is required to persist through the life-time of a wool product.
  • Application of a 5-10 fold excess of active ingredient above the minimum active level ensures insect protection even after 80-90% losses through volatility, exposure to light, and cleaning (washing, shampooing and drycleaning).
  • Exposures of 1 , 2, 3, and 4 weeks correspond to blue scale ratings of 3, 5, and 6 respectively.
  • Bracketed values in the body of the table are percentages of the initial application remaining after the specified exposure.
  • Compound (IV) has more than adequated light fastness for a commercial insect-resist treatment. Under these same accelerated testing conditions, only 40-50% of an initial application of permethrin would remain.
  • Compound (IV) has similar washing performance and better drycleaning resistance. Losses in handwashing are confirmed by both insect bioassay (Table 5) and by chemical analysis (Table 6, and Fig. 3). Losses in drycleaning are small (Table 6, Fig. 4).
  • Bracketed values in the body of the table are percentages of the initial amount remaining after the specified exposure.
  • Compound (IV) has little direct beetle activity at this treatment level, it greatly enhances the effect of the 4-hydroxybenzoic acid ester.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Biochemistry (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne un procédé de protection antimite destiné à un produit en laine ou contenant de la laine, ce procédé comprenant le traitement du produit en laine ou contenant de la laine avec une quantité efficace d'un composé selon la formule (I).
EP94926721A 1993-09-06 1994-09-06 Composition insecticide Withdrawn EP0717591A4 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
AUPM1031/93 1993-09-06
AUPM103193 1993-09-06
PCT/AU1994/000527 WO1995007021A1 (fr) 1993-09-06 1994-09-06 Composition insecticide

Publications (2)

Publication Number Publication Date
EP0717591A1 EP0717591A1 (fr) 1996-06-26
EP0717591A4 true EP0717591A4 (fr) 1996-08-28

Family

ID=3777177

Family Applications (1)

Application Number Title Priority Date Filing Date
EP94926721A Withdrawn EP0717591A4 (fr) 1993-09-06 1994-09-06 Composition insecticide

Country Status (4)

Country Link
EP (1) EP0717591A4 (fr)
JP (1) JPH09502189A (fr)
NZ (1) NZ273244A (fr)
WO (1) WO1995007021A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5506251A (en) * 1994-11-16 1996-04-09 Rohm And Haas Company Synergisic insecticidal compositions
AU1214197A (en) * 1995-12-21 1997-07-17 Wool Research Organisation Of New Zealand Inc. A method for insect-resist treatment of carpet and textiles
US6723531B2 (en) 1996-04-05 2004-04-20 The Salk Institute For Biological Studies Method for modulating expression of exogenous genes in mammalian systems, and products related thereto
EP0943026B1 (fr) * 1996-07-24 2003-12-17 Wool Research Organisation Of New Zealand (Inc.) Procede de traitement insectifuge pour tapis, textiles et produits isolants

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05112405A (ja) * 1991-10-22 1993-05-07 Rohm & Haas Co 殺虫組成物
EP0632958A1 (fr) * 1993-07-06 1995-01-11 Rohm And Haas Company Composition et procédé de protection de matériau kératinique contre l'attaque d'insectes digénant la kératine

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK483586A (da) * 1985-10-21 1987-04-22 Rohm & Haas Insecticide n'-substituerede-n,n'-diacylhydraziner
CA1338289C (fr) * 1986-01-22 1996-04-30 Raymond August Murphy Derives de substitution en n' de n-alkylcarbonyl-n'-acylhydrazines insecticides
CA1295618C (fr) * 1986-02-28 1992-02-11 Adam Chi-Tung Hsu N-acyl-n'-alkylcarbonylhydrazines substituees en n', a proprietes insecticides
CA1281716C (fr) * 1986-05-01 1991-03-19 Raymond August Murphy Derives de substitution en n et en n' de n,n'diacylhydrazines, insecticides
EP0253468B1 (fr) * 1986-07-14 1991-11-06 Rohm And Haas Company Dérivés hétérocycliques à 6 chaînons de N,N'-diacyl-hydrazines N'-substituées
IE59962B1 (en) * 1986-09-26 1994-05-04 Rohm & Haas Five-membered heterocyclic derivatives of n'-substituted-n, n'-diacylhydrazines
AU599124B2 (en) * 1987-04-09 1990-07-12 Dow Agrosciences Llc Insecticidal N-(optionally substituted) -N'- substituted-N, N'-disubstituted hydrazines
NZ229536A (en) * 1988-06-15 1992-05-26 Rohm & Haas N'-substituted-n'-substituted carbonyl-n-substituted carbonyl-hydrazines and pesticidal compositions
NZ228936A (en) * 1989-05-01 1992-04-28 Rohm & Haas Method for treating insect infestation in rice plants comprising applying diacylhydrazine derivatives

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05112405A (ja) * 1991-10-22 1993-05-07 Rohm & Haas Co 殺虫組成物
EP0632958A1 (fr) * 1993-07-06 1995-01-11 Rohm And Haas Company Composition et procédé de protection de matériau kératinique contre l'attaque d'insectes digénant la kératine

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHEMICAL PATENTS INDEX, DOCUMENTATION ABSTRACTS JOURNAL Week 9332, Derwent World Patents Index; AN 93-185131, XP002007519 *
See also references of WO9507021A1 *

Also Published As

Publication number Publication date
EP0717591A1 (fr) 1996-06-26
WO1995007021A1 (fr) 1995-03-16
NZ273244A (en) 1997-11-24
JPH09502189A (ja) 1997-03-04

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