Method for treating wood against the attack of harmful fungi

Details Method for treating wood against the attack of harmful fungi Method for treating wood against the attack of harmful fungi

2001-01-17

2003-05-06

Levy, Neil S. (Department: 1616)

Drug, bio-affecting and body treating compositions

Preparations characterized by special physical form

Biocides; animal or insect repellents or attractants

C424S406000, C504S116100, C504S126000, C504S130000, C504S133000, C504S134000, C504S135000, C504S138000, C504S139000, C504S140000, C514S394000, C514S395000

Reexamination Certificate

active

06558685

ABSTRACT:

The present invention relates to multi-phase aqueous suspoemulsions and to their use for the treatment of timber against attack by fungal timber pests.
The fungicidal action of fenpropimorph (4-[3-{4-tert-butylphenyl}-2-methylpropyl]-2,6-cis-dimethylmorpholine) is generally known (cf. DE-A 26 56 747).
It is furthermore known to employ triazole compounds in timber protection [propiconazole: U.S. Pat. No. 4,079,062; tebuconazole: EP-A 40 345 and EP-A 52 424; cyproconazole: EP-A 131 684 and EP-A 555 186].
WO-A 95/16349 discloses fungicidal mixtures and compositions comprising them for crop protection which comprise, as active ingredients, fenpropimorph and a triazole compound.
EP-A 72 156 discloses the synergistic action of a mixture of fenpropimorph and prochloraz against phytopathogenic fungi.
Synergistic mixtures of triazole compounds are also customary in the protection of timber [propiconazole+tebuconazole: EP-A 393 746].
DE-A 43 40 853 teaches a synergistic mixture for use in the protection of timber which, besides a copper compound and an alkanolamine, comprises a triazole compound and a further fungicide, for example fenpropimorph.
Furthermore, EP-A 425 857 discloses the synergistic action of a mixture of fenpropimorph and epoxiconazole against fungal pests of materials.
WO 97/39865 describes synergistic mixture of fenpropimorph and various triazoles for use in the protection of timber. The combination of such mixtures with benzimidazoles, or with precursors liberating them, is not described.
EP 707 445 describes suspoemulsions based on the triazole epoxiconazole for crop protection. However, the solvents used therein are only poorly suited to use in the protection of timber since they volatilize relatively rapidly, owing to their high vapor pressure, which may lead to destabilization of the oil phase or to breaking of the emulsion. In addition, most of the solvents stated in EP-A 707,745 suffer from odor problems in enclosed spaces if a use as timber treatment agent is considered.
Moreover, the treatment systems in crop protection and timber protection differ greatly in as far as, as a rule, aqueous crop protection spray mixtures as tank mixes only require that the emulsion remain stable over, as a rule, a few hours and that these tank mixes can additionally be applied with the aid of a stirrer. In the protection of timber, in contrast, aqueous treatment systems are meant to be stable over weeks and months. In this context, the emulsions, suspoemulsions or microemulsions utilized by the timber are typically made up with treatment concentrates which have been made up freshly with water without this allowing the stability of an immersion bath mix to be adversely affected.
In contrast to crop protection, aqueous emulsions, microemulsions or, for example, suspoemulsions used in the protection of timber are thus subject to quite different quality criteria so that prior-art solutions to application problems can be transferred from crop protection to the protection of timber in terms of inception only.
Formulations with carbendazim (BCM) as biocides, fungicides and timber preservatives have been described repeatedly in the literature. The problem with BCM is that virtually no water-insoluble solvents are known which are capable of dissolving BCM in high concentration and thus to stabilize it as emulsion or microemulsion together with surfactants. Water-soluble solvents, in contrast, would lead to the precipitation or crystallization of BCM after high dilution.
This can be circumvented firstly by using BCM salts, where protonation with mineral acids exploits the very weakly basic character of BCM. Thus, CA 97:51133 describes phosphoric acid salts of BCM. However, such BCM salts are quite unsuitable for practice conditions in high dilution, in particular when using weakly basic tap water, since deprotonation, crystal formation or precipitation of BCM would follow very rapidly, and BCM would then be present in the form of coarse particles around >>10 mm in size, in which case it is virtually no longer effective and sediments very rapidly.
Furthermore, low pH values are frequently responsible for corrosion of timber preservative application plants.
A further possibility is found in JP 03251507 by suppressing sedimentation or crystal growth of BCM by means of xanthans. However, this generally results in very high xanthan contents of approx. 0.2% based on the use concentration or the tank mix or immersion bath mix. Based on the finished formulation, however, the xanthans would have to be employed like the active ingredients in the 100 g range of the finished formulation. This is not possible technically since xanthan gum contents in the suspoemulsion concentrate starting at as little as approx. 0.2% cause extremely high viscosity and such formulations are no longer flowable and give more gel-like, or even solid, products which are entirely unsuitable for the process.
It is an object of the present invention to develop liquid formulations with high concentrations of active ingredients comprising carbendazim and active ingredients from the class of the morpholines, amines and/or cycloamines or triazoles which, when applied in the protection of timber as suspoemulsions, exhibit good storage stability of the suspoemulsion and good long-term stability of the aqueous use product. Another object is to dispense as far as possible with readily vaporizable and malodorous solvents which are a health hazard, in particular chlorinated solvents. A further object was to formulate the active ingredients in high concentrations.
The systems according to the invention were intended to identify timber preservation methods which are improved from the economical and ecological points of view.
We have found that this object is achieved in accordance with the invention by multi-phase aqueous suspoemulsions comprising, as essential components,
a) 1 to 50% by weight of a fungicidal active ingredient from the class of the benzimidazoles or the precursors liberating them of the formulae I.1. to I.4 as microsuspended solids particles,
methyl 1-(butylcarbamoyl)benzimidazol-2-ylcarbamate (I.1)
methyl benzimidazol-2-ylcarbamate (I.2)
2-(2′-furyl)benzimidazole (I.3)
2-(1,3-thiazol-4-yl)benzimidazole (I.4)
b) an emulsion comprising
b
1
) a fungicidal active ingredient selected from among compounds of the formulae II.1. to II.5 and
[n=10,11,12 (60-70%) or 13]
 and, in combination with b
1
), at least one component b
2
) or b
3
)
b
2
) fungicidal active ingredients selected from among the azoles III.1. to III.18
1-[(2RS,4RS;2RS,4SR)-4-bromo-2-(2,4-dichlorophenyl)tetrahydrofuryl]-1H-1,2,4-triazole (III.1)
2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (III.2)
(±)-4-chloro-4-[4-methyl-2-(1H-1,2,4-triazol-1-yl-methyl)-1,3-dioxolan-2-yl]phenyl 4-chlorophenyl ether (III.3)
(E)-(R,S)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol (III.4)
(Z)-2-(1H-1,2,4-triazol-1-ylmethyl)-2-(4-fluorophenyl)-3-(2-chlorophenyl)oxirane (III.5)
4-(4-chlorophenyl)-2-phenyl-2-(1H-1,2,4-triazolylmethyl)butyronitrile (III.6)
3-(2,4-dichlorophenyl)-6-fluoro-2-(1H-1,2,4-triazol-1-yl)quinazolin-4(3H)-one (III.7)
bis(4-fluorophenyl)(methyl)(1H-1,2,4-triazol-1-yl-methyl)silane (III.8)
(R,S)-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol (III.9)
(1RS,5RS;1RS,5SR)-5-(4-chlorobenzyl)-2,2-dimenthyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol (III.10)
N-propyl-N-[2-(2,4,6-trichlorophenoxy)ethyl]-imidazole-1-carboxamide (III.11)
(±)-1-[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole (III.12)
(R,S)-1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol (III.13)
(±)-2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-yl)-propyl 1,1,2,2-tetrafluoroethyl ether (III.14)
(E)-1-[1-[[4-chloro-2-(trifluoromethyl)phenyl]-imino]-2-propoxyethyl]-1H-imidazole (III.15)
(RS)-2,4′-

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