DK158537B - BACTERICIDE AND FUNGICIDE AGENT CONTAINING A MIXTURE OF TRIALKYLTYL COMPOUNDS AND 2,5-DIMETHYL-N-CYCLOHEXYL-N-METHOXY-3-FURANCARBONIC ACID AMIDE - Google Patents

Abstract

1. Claims for the contracting states : BE, CH, DE, FR, GB, IT, LI, LU, NL, SE Bactericidal and fungicidal agent containing as active substances a) trialkyltin compounds having a total number of carbon atoms in the alkyl groups bonded to the tin of from 9 to 12 or triphenyltin compounds, and b) 2,5-dimethyl-N-cyclohexyl-N-methoxy-3-furanecarboxylic acid amide in a ratio by weight of from 4 : 1 to 1 : 4. 1. Claims for the contracting state : AT Use of a mixture of a) trialkyltin compounds having a total number of carbon atoms in the alkyl groups bonded to the tin of from 9 to 12 or triphenyltin compounds, and b) 2,5-dimethyl-N-cyclohexyl-N-methoxy-3-furanecarboxylic acid amide in a ratio by weight of from 4 : 1 to 1 : 4 as bactericidal and fungicidal agents.

Description

in

DK 158537B

The present invention relates to an agent which, with bactericidal and fungicidal properties, is suitable as a disinfectant, wood preservative, to make textiles, plastics and building materials bactericidal and fungicidal or as a preservative or to make ironing systems biocidal.

The composition of the invention is characterized in that it contains as active compounds a mixture of a) trialkyltin compounds having a total C-number of the alkyl groups attached to the individual tin atoms of 9-12 or triphenyltin compounds and b) 2,5-dimethyl -N-cyclohexyl-N-methoxy-3-furancarboxylic acid amide in the weight ratio of 4: 1 to 1: 4.

According to the invention, the active compounds are preferably included in the weight ratio 2: 1 to 1: 2.

The high effect of triorganotin compounds on microorganisms, e.g. harmful fungi and bacteria are known. The optimum effect for this compound class exists when the total C number of the alkyl groups attached to the individual tin atoms is 9-12. Shorter or longer groups reduce the biocidal effect. Although triorganotin compounds exhibit a relatively broad spectrum of efficacy, they have different microorganisms, e.g. However, the effect of gram-negative bacteria and certain bladder fungi is relatively weak.

The substance known as biocide 2,5-dimethyl-N-cyclohexyl-25N-methoxy-3-furancarboxylic acid amide exhibits a good effect against a number of wood-destroying fungi, but against bacteria and certain fungi, e.g. Cladosporum herbarum, Trichoderma viride and some Aspergillus species, there is no or only a very weak effect.

It has now surprisingly been found that the present combinations of the triorganotin compounds with 2,5-dimethyl-N-cyclohexyl-N-methoxy

DK 158537B

2 3-Furancarboxylic acid amide has a synergistic effect on microorganisms. The agent according to the invention extends the spectrum of effects of the individual substances considerably and amplifies the inhibitory effect against microorganisms, against which the individual substances themselves already have a good effect (see Table 1-4).

In particular, the agent of the invention can be used for tree protection, since besides preventing the degradation due to wood-destroying fungi, protection against bacterial attacks is also obtained. Bacteria cause no degradation of the tree, but can favor an attack by fungi.

The agent is introduced into the wood in the form of solutions, optionally with dyes and auxiliaries, by ironing, spraying or dipping.

In addition, the agent of the invention can be used to make textiles, plastics and building materials biocidal, suitably used in the form of compositions such as solutions, emulsions, dispersions with or without binder or with solid carriers, e.g. diluents and, optionally, with the addition of wetting agents, adhesives, emulsifiers and dispersants.

The concentration of active substance is usually in the range of 0.1 to 5% and is determined by the application requirements.

Example 1

A colorless, non-binder-containing preparation of 2 parts by weight of tri-n-butyltin linoleate 2 parts by weight of 2,5-dimethyl-N-cyclohexyl-N-methoxy-3-furan = c arbonic acid amide

DK 158537B

3 6 parts by weight of diethylene glycol monobutyl ether 90 parts by weight of high-boiling test gasoline (crystal oil 60) exhibit good permeability and can e.g. used as a foundation for building wood.

Example 2

A preparation (colored lasure) of 1.3 parts by weight of bis- (tri-n-butyltin) oxide 2.2 parts by weight of 2,5-dimethyl-N-cyclohexyl-N-methoxy-3-furan = carboxylic acid amide 30 parts by weight of alkyd resin (synthetic) MF 620, 60% g) 0.5 parts by weight of sedatives 0.5 parts by weight of antifouling 8.5 parts by weight of paste of iron oxide red 1.5 parts by weight of paste of iron oxide 15 5 parts by weight of diethylene glycol monobutyl ether 50.5 parts by weight of high boiling test gasoline (crystal oil 60) is suitable for coating window frames, doors, wooden shutters, etc.

Example 3 15 parts by weight of bis- (tri-n-butyltin) oxide 15 parts by weight 2,5-dimethyl-N-cyclohexyl-N-methoxy-3-furan = carboxylic acid amide 70 parts by weight non-ionic emulsifier (Marlomet ISM).

The clear blend gives a ratio of 1: 5 to 1:30 diluted 25 with water stable emulsions which can be applied to protect freshly swollen wood by application, spraying or dipping.

DK 158537B

Table 1 4

To compare the effect, round paper filters (5.5 cm diameter) were soaked with the ethanolic solutions provided in the table, dried in the air and then placed 5 in Petri dishes on plate count agar seeded with bacterial suspension. The plates were incubated for 2 days at + 37 ° C. Then the sizes of the inhibition zones about the filter were determined: Inhibition zone in mm

Bacillus Proteus wt% in Bacillus mesente vulgaris

Active substance ethanol subtilis ricus

Bis (tributyltin) oxide 0.5 2-3 3-5 0-1 (TBTO) 0.75 5-7 5-6 2-3 1.5 10-12 8-10 5-6

Tributyltin benzoate 1.0 5-6 5-7 2-3 (TBTB) 2.0 10-12 10-12 5-6

Tributyltin = naphthenate 1.5 4-6 3-5 0-1 (TBTN) 3.0 8-10 7-9 1-2

Tributyltinlino = 1.5 4-5 3-5 0-1 leat 2.0 4-5 6-8 1-2 (TBTL) 3.0 8-10 7-9 1-3 2,5-dimethyl-N- cy = 1.0 0-1 0-1 0 clohexyl-N-methoxy-3-furancarboxylic acid amide 2.0 0-1 0-1 0 2.5 1-2 1-2 0 3.0 2-4 1- 2 0-1

Table 1 (continued)

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5

Provision zone in irm

Bacillus Proteus:% by weight in Bacillus mesente vulgaris Active substance ..... thanol subtilis. ricus TBTO: 2,5-dime = 0.5: 1.0 6-8 4-6 2-3 thyl-N-cyclohexyl-5; 1 5 8_10 5_7 3-4 N-methoxy-3-furan carboxylic acid amide 0.5: 2.0 8-10 8-10 4-5 0.75: 1.0 8-10 8-10 6-8 0.75: 1.5 9-11 9-11 6-8 TBTB : 2,5-dime = 1.0: 1.0 10-12 10-12 4-6 Thyl-N-cyclohexyl-N-methoxy-3-furanecarboxylic acid amide TBTN: 2,5-dime = 1.5: 1.0 8-10 8-10 5-7 Thyl-N-cyclohexyl-N-methoxy-3-furanecarboxylic acid amide TBTL: 2,5-dime = 1.5: 1.0 6-7 6-8 3 -4 thyl-N-cyclohexyl-N-methoxy-3-furanic carboxylic acid amide 1.5-2.0 7-9 8-10 4-5 2.0: 1 6-8 6-8 4-5 2 , 0: 1.5 8-10 8-10 4-5 O sample 00 0

Table 2 6

t, DK 158557B

Following the method of Table 1, wet round paper filters were applied to biomalt agar sprayed with spore suspensions of test sponges and incubated for 3 weeks at + 30 ° C. Then the inhibition zones around the filters were determined · Inhibition zone in mm (FZ = color change zone of sporulation)

Cladospo-Tricho -% by weight in Poria monomer herderma Active substance ethanol ticula barum viride (FZ) TB TO 0.75 8-10 6-7 2-3 (8-10) 1.5 12-15 10- 12 3-5 (15) TBTN 1.5 5-7 0-1 1-2 (6-8) 3.0 8-10 1-2 2-3 (10-12) 2,5-dimethyl-1, 0 0-1 0 * 0 * N-cyclohexyl- * * N-methoxy-3- *, O x Auu furan carbon 3.0 8-10 0 * 0 * Acid amide TBTO: 2,5-dime = 0.75 : 1.0 7-7 4-6 (15) Thyl-N-cyclohexyl-N-methoxy-3-furanecarboxylic acid amide TBTN: 2,5-dime = 1.5: 1.0> 2-3 -3 (10-12) thyl-N-cyclohexyl-N-methoxy-3-furanecarboxylic acid amide O sample Q * Q * & = strong growth of the sample.

Table 3

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7

Following the method of Table 2, the inhibition zone of the filters was determined: Inhibition zone in mm (FZ = color change zone of sporulation) wt% in Pullularia Aspergillus Aspergillus Active substance ethanol pulluians. ustus. versicolor TBTB 1.0 2-3 3-4 2-3 2.0 4-6 5-7 4-6 TBTL 1.5 0 0-1 1-2 3.0 0-1 1-2 3-4 2,5-dimethyl - 1.0 01 0 1 01 N-cyclohexyl N-methoxy-3- '. 1 1 furan carbon-3.0 0 0 0 acid amide TBTB: 2,5-dime-1.0: 1.0 6-8 2-3 4-6 thyl-N-cyclohexyl-FZ (15) N-methoxy-3 -furan-carboxylic acid amide TBTL: 2,5-dime-1,5: 1,0 2-3 0-1 3-4 thyl-N-cyclohexyl-FZ (6-8) N-methoxy-3-furan-carboxylic acid amide O sample 0 1 0 1 0 1 = strong growth of the sample.

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8

Table 4

Following the method of Table 2, the inhibition zones about the filters were determined: Inhibition zone x mm (FZ = color change zone of sporulation) wt% in Pullularia Trichoderma

Active substance ethanol. pullulans viride 2,5-dimethyl-1,0 0 * 0 * N-oyclohexyl-, n * n * N-methoxy-3- '. .

furan carbon 2.0 0 0 acid amide 2f5 0 * 0-1 * TBTO 0.5 3-4 2-3 FZ (8-10) 0.75 4-5 3-4 FZ (10-12) TBTL 1.5 0 0 FZ (6-8) 2.0 0-1 0-1 FZ (8-10) TBTO: 2.5-dime 0.5: 1.0 4-5'FZ (8-10) 4- 5 FZ (8-10) Thi-N-cyclohexyl · 0.5: 1.5 5-6 FZ (8-10) 5-6 FZ (10-12) N-methoxy-3-furanic acid amide 0.5: 2.0 6-7 FZ (10-12) 5-6 FZ (10-12) 0.75: 1.0 5-6 FZ (10-12) 5-7 FZ (12-15) 0.75: 1.5 7-8 FZ (10-12) 6-8 FZ (12-15) TBTL: 2.5-dime 1.5: 1.0 1-2 FZ (5-7) 0 -1 FZ (6-8) Thi-N-cyclohexyl-5: 1.5 2-3 FZ (6-8) 1-2 FZ6-8) N-Methoxy-3-furanic acid amide 1 , 5: 2.0 3-4 FZ (8-10) 2-3 FZ (8-10) 2.0: 1 3-4 FZ (8-10) 2-3 FZ (10-12) 2.0 : 1.5 3-4 FZ "(10-12) 3-4 FZ (10-12) = strong overgrowth of the sample.

Claims (3)

Bactericidal and fungicidal agent, characterized in that it contains as active compounds a mixture of a) trialkyltin compounds having a total C number of the 9-12 or triphenyltin compounds alkyl groups attached to the 5 individual atoms; dimethyl-N-cyclohexyl-N-methoxy-3-furancarboxylic acid amide in a weight ratio of 4: 1 to Γ: 4. An agent according to claim 1, characterized in that the 10 active compounds are included in the weight ratio 2: 1 to 1: 2. Use of the mixture according to claim 1 for the manufacture of wood preservatives.