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
  • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
  • A01N33/02—Amines; Quaternary ammonium compounds
  • A01N33/12—Quaternary ammonium compounds

Definitions

• the present invention relates to the use of certain very lo chain quaternary ammonium compounds of low phytotoxicity plant protection for controlling and combating fungi.
• fungicidal compositions comprising such compoun either alone or in combination with other fungicidally acti agents, methods for controlling or combating fungi in plants applying said compositions to the plants, and the use of su compounds as additives to fungicidal compositions.
• ATAX alkylbenzyl-dimeth ammonium salts
• DADA dialkyldimethyl ammonium salts
• VLCQAC very lon chain quaternary ammonium compound
• ATAX formula I
• AK formula II
• DADAX formula III
• R is straight chained or branched alkyl or alkylene with more than 17 carbon atoms
• R* and R" that may be the same or different are straight or branched alkyl or alkylene with more than 11 carbon atoms
• X is a halogen, acetate, sulfate, or phosphate anion.
• Quaternary ammonium compounds with shorter chain lengths than VLCQACs are widely used as disinfectants and as pharma- ceutical preservatives.
• dicocodimethyl ammonium chloride (coco being a mixture of C 8 to C 18 -alkyl) for combating Podosphaera leucotricha on overwintering apple buds has been exemplified in Offenlegungsschrift 2408662.
• the Phytotoxicity of a 5% aqueous solution of didecyl dimethyl ammonium bromide (DDDAB) has been noted in this work too. No other compounds were exemplified in this study.
• the present invention reports for the first time the use of VLCQACs as fungicides obtaining improved disease control in plants. It has here been demonstrated that a synergistic effect of VLCQACs and another fungicidally active compound or co po- sition is often obtained. This synergistic effect allows application of the other fungicide in considerably lower dosages than the ones usually applied while still retaining the same or improved control effect of the fungal pathogen.
• Examples of other fungicides which can be combined with t VLCQACs of the invention include the residual fungicidal d thiocarbamates (e.g.
• aneb BASF-maneb 80, BASF and mancoz (dithane M45/LF, Kemisk Vaerk K ⁇ ge, Denmark)
• the diluent or carrier in the compositions of the inventio can be a solid or a liquid optionally in association with a other surface-active ingredient, for example a dispersin agent, emulsifying agent or wetting agent.
• Suitable surface active include nonionic agents as condensation products o fatty acid esters of polyhydric alcohol ethers, e.q. sorbita fatty acid esters, condensation products of such esters wit ethylene oxide e.q.
• polyoxyethylene sorbitan fatty acid esters block copolymers of ethylene oxide and propylene oxide, ace tylenic glycols such as 2,4,7,9-tetramethyl-5-decyn-4,7-diol or ethoxylated acetylenic glycols.
• concentration of the VLCQACs in the compositions of th present invention when used alone or in combination with conventional fungicide, as applied to plants is preferabl within a range of 0,001 to above 1,0 per cent by weight especially 0,01 to 0,5 per cent by weight.
• the amount of VLCQACs can var widely and can be, for example, in the range from about 1% t about 100% by weight, preferably from about 5% to 30% by weigh of the composition.
• the concentration of the other fungicidally active ingredien in the mixed composition of the present invention, as applie to plants is preferably within the range of 0,001 to 10 pe cent by weight , especially 0,01 to 5 per cent by weight.
• the amount of active ingredient can vary widely and can be, for example, from 5 to 80 per cent by weight of the composition.
• the active VLCQAC preparation or the compositions of the invention can be applied directly to the plant by, for examp ⁇ le, spraying or dusting either at a time when an attack of the fungus has been established and determined on the plant for combating the fungus or fungi or before the appearance of fungus as a protective measure.
• the prefer ⁇ red mode of application is by foliar spraying. It is generally important to obtain good control of fungi in the early stages of plant growth as this is the time when the plant can be most severely damaged.
• the spray or dust can conveniently contain a pre- or post-emergence herbicide if this is thought necessary.
• a suitable liquid or solid composition When the active VLCQAC preparation of the invention is applied directly to the plant a suitable rate of application is from 0.01 to 10 kg per hectare, preferably from 0.05 to 5 kg per hectare.
• VLCQACs used in the Examples of this specification is listed.
• L n-C 12 H 25 (lauryl)
• M n-C 14 H 29 (myristyl)
• C n-C 16 H 33 (cetyl)
• S n-C 18 H 37 (stearyl)
• Ei n-C 20 H 41 (eicosyl)
• Be n-C 22 H 45 (behenyl)
• DD (n-C 10 H 21 ) 2 (didecyl)
• DL (n- c 12 H 25 ) 2 (dilauryl)
• DM (n-C 14 H 29 ) 2 (dimyristyl)
• DS (n-C 18 H 37 ) 2 (distearyl)
• T (CH 3 ) 3 (trimethyl)
• D (CH 3 ) 2 (dimethyl)
• K C 6 H 5 - CH 2 N +
• LTAC, MTAC and CTAC were prepared by quaternisation of alkyldi- methylamine with methyl chloride at a pressure of 3 kg/cm 3 in water. A 25% aqueous solution was used.
• STAC, 20/22TAC and BeTAC were prepared by quaternisation of alk ldimethy1amine with methyl chloride at a pressure of 3 kg/cm 3 in acetone followed by crystallization.
• LKB was prepared by reaction of alkyldimethyl-amine in water with benzyl bromide. A 25% aqueous solution was used.
• EiKC was prepared by reaction of alkyl-dimethylamine with benzyl chloride in refluxing acetone followed by crystallization.
• DLDAB and DMDAB were prepared by reaction of alkyldime- thylamine with alkylbromide.
• the HPLC method was a modified version of the one published by Helboe [Journal of Chromatography 261. 1983, 117-122] based on chromatography of ion pairs of the QAC with an UV absorbing counterion.
• Helboe Journal of Chromatography 261. 1983, 117-122
• chromatography of ion pairs of the QAC with an UV absorbing counterion.
• Potato plants (Variety: Sava ecology, grown 14 days in 7 cm plastic pots. 1 plant/pot) were sprayed with aqueous solutions of the compounds shown in the following Table II, the concentration of active substance being listed in the Table. The solutions furthermore contained 0.1% Tween ® 20 and 5% ethanol.
• the potato plants were incubated in humid chambers.
• the dark/light interval during the incubation period was 6 hrs/18 hrs.
• the degree of control and phytotoxici ⁇ ty was assessed 6 days after the inoculation.
• Table IV shows that CTAC and DDDAC generally have the best score of MIC values in this test system where there are no problems with phytotoxicity. However, it is interesting to note that 20/22-TAC has the lowest MIC value for Phytophthora infestans.
• VLCQACs are very efficient fungicides in this test system too. Also, it is seen that the phytotoxicity apparently poses a problem to the QACs of short chain length.
• Leaves of cucumber were sprayed with aqueous solutions/ suspensions of QACs approximately 24 hours before inoculation with a spore suspension of P. cubensis. The results were evaluated after 7 days, and are shown in Table VI below.
• Potato plants were sprayed with solutions containing Dithane ® , BeTAC (dissolved in 5% aqueous ethanol) and 0.1% Tween ® 20. After 1 day, the plants were inoculated with sporangia suspen ⁇ sion of Phytophthora infestans and incubated 6 days at 18°C/ 18 hrs light - 13°C/6 hrs dark and a relative humidity of 80%. Evaluation of the results gave following Table VII: TABLE VII
• Potato plants were sprayed with a solution containing BeTAC and/or the fungicide Ridomil ® MZ and 0.1% W/W Tween ® 20.
• BeTAC was dissolved in 5% ethanol.
• Ridomil ® MZ was diluted to a concentration of 0.005 mg/ml (1:1000 of normal dose) .
• the conditions were as in Example 7.
• VLCQAC STAC C 18 -chain was less phytotoxic than LKB (C 12 -chain) and MTAC (C 1 -chain) .

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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)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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• 1990
  • 1990-04-06 DK DK86290A patent/DK86290D0/da not_active Application Discontinuation
• 1991
  • 1991-04-05 AU AU76526/91A patent/AU662292B2/en not_active Ceased
  • 1991-04-05 WO PCT/DK1991/000096 patent/WO1991015120A1/en not_active Application Discontinuation
  • 1991-04-05 CA CA002079998A patent/CA2079998A1/en not_active Abandoned
  • 1991-04-05 HU HU923167A patent/HUT62753A/hu unknown
  • 1991-04-05 IE IE113791A patent/IE911137A1/en unknown
  • 1991-04-05 EP EP19910907783 patent/EP0523158A1/en not_active Withdrawn
  • 1991-04-05 JP JP91506767A patent/JPH05505614A/ja active Pending

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