NO145605B - USE OF N- (1,1,2,2-TETRACHLORO-2-FLUORETHYLTIO) -METHANE SULPHONANILIDE TO FIGHT AGAINST CONIOPHORA CEREBELLA IN THREE - Google Patents
USE OF N- (1,1,2,2-TETRACHLORO-2-FLUORETHYLTIO) -METHANE SULPHONANILIDE TO FIGHT AGAINST CONIOPHORA CEREBELLA IN THREE Download PDFInfo
- Publication number
- NO145605B NO145605B NO761398A NO761398A NO145605B NO 145605 B NO145605 B NO 145605B NO 761398 A NO761398 A NO 761398A NO 761398 A NO761398 A NO 761398A NO 145605 B NO145605 B NO 145605B
- Authority
- NO
- Norway
- Prior art keywords
- tetrachloro
- fluorethyltio
- sulphonanilide
- methane
- wood
- Prior art date
Links
- 241001626940 Coniophora cerebella Species 0.000 title claims description 6
- 239000002023 wood Substances 0.000 claims description 11
- 206010061217 Infestation Diseases 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 13
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- SVIKNKPDPGCMAE-UHFFFAOYSA-N n-phenyl-n-(1,1,2,2-tetrachloro-2-fluoroethyl)sulfanylmethanesulfonamide Chemical compound FC(Cl)(Cl)C(Cl)(Cl)SN(S(=O)(=O)C)C1=CC=CC=C1 SVIKNKPDPGCMAE-UHFFFAOYSA-N 0.000 description 5
- 241000233866 Fungi Species 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000003755 preservative agent Substances 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 230000004580 weight loss Effects 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- APQHKWPGGHMYKJ-UHFFFAOYSA-N Tributyltin oxide Chemical compound CCCC[Sn](CCCC)(CCCC)O[Sn](CCCC)(CCCC)CCCC APQHKWPGGHMYKJ-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 2
- 241000018646 Pinus brutia Species 0.000 description 2
- 235000011613 Pinus brutia Nutrition 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000001717 pathogenic effect Effects 0.000 description 2
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
- KMYWXFCMGQZEMC-UHFFFAOYSA-N 3,3-dichloro-2h-naphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(Cl)(Cl)CC(=O)C2=C1 KMYWXFCMGQZEMC-UHFFFAOYSA-N 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 239000005745 Captan Substances 0.000 description 1
- 241000223932 Eimeria tenella Species 0.000 description 1
- 241001492222 Epicoccum Species 0.000 description 1
- 240000000731 Fagus sylvatica Species 0.000 description 1
- 235000010099 Fagus sylvatica Nutrition 0.000 description 1
- 239000005789 Folpet Substances 0.000 description 1
- 241000427940 Fusarium solani Species 0.000 description 1
- 241000228168 Penicillium sp. Species 0.000 description 1
- 241000813090 Rhizoctonia solani Species 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 1
- MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 1
- 229940117949 captan Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 description 1
- 244000000004 fungal plant pathogen Species 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- SKIVFJLNDNKQPD-UHFFFAOYSA-N sulfacetamide Chemical compound CC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 SKIVFJLNDNKQPD-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 239000003171 wood protecting agent Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/34—Organic impregnating agents
- B27K3/38—Aromatic compounds
- B27K3/42—Aromatic compounds nitrated, or nitrated and halogenated
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Forests & Forestry (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Catalysts (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Foreliggende oppfinnelse vedrorer en ny anvendelse for beskyttelse av tre mot angrep av den treødeleggende sopp Coniophora cerebella ived hjelp av den kjente forbindelse. The present invention relates to a new application for the protection of wood against attack by the wood-destroying fungus Coniophora cerebella by means of the known compound.
N-(1,1,2,2-tetrakloro-2-fluoroetyltio) -metansulfonanilid, som trebeskyttelsesmiddel. N-(1,1,2,2-tetrachloro-2-fluoroethylthio)-methanesulfonanilide, as a wood preservative.
Denne forbindelses fremstilling og hittil kjente anvendelse er eksempelvis beskrevet i engelsk patent nr. 1.242.265 og nr. 1.242.266, av hvorfra det er kjent at forbindelsen er virksom overfor Eimeria tenella. Fra de samme patentskrifter er det også kjent at forbindelsene utover accaricide egenskaper også utviser fungicid aktivitet overfor forskjellige plantepatogene sopp så som eksempelvis Rhizoctonia solani og Fusarium solani samt. aktivitet overfor sopp som Aspergillus niger og penicil-lium sp., som kan kan forårsake misfarging av maling og tre-overflater. The preparation and hitherto known use of this compound is described, for example, in English patent no. 1,242,265 and no. 1,242,266, from which it is known that the compound is effective against Eimeria tenella. From the same patent documents, it is also known that the compounds, in addition to acaricidal properties, also exhibit fungicidal activity against various plant pathogenic fungi such as, for example, Rhizoctonia solani and Fusarium solani as well. activity against fungi such as Aspergillus niger and penicillium sp., which can cause discoloration of paint and wooden surfaces.
I betraktning av de store forskjeller som finnes mellom forskjellige soppslag betyr det at et stoff som er virksomt mot en klasse ikke nodvendigvis er virksomt mot andre klasser. In view of the large differences that exist between different types of fungi, this means that a substance that is effective against one class is not necessarily effective against other classes.
Det har nu overraskende vist seg at den nevnte forbindelse N-(1,1, 2,2-tetrakloro-2-fluoroetyltio)-metansulfonanilid, er meget virksom mot den treødeleggende sopp Coniophora cerebella. It has now surprisingly been shown that the aforementioned compound N-(1,1,2,2-tetrachloro-2-fluoroethylthio)-methanesulfonanilide is very effective against the wood-destroying fungus Coniophora cerebella.
Forbindelsens aktivitet er meget hoy, ikke bare i sammenligning med aktiviteten for andre kjente plantepatogene fungicider, hvorav mange slett ikke er virksomme ovenfor treodeJeggende sopp, men også sammenlignet med aktiviteten for kjente og meget utbredte trebeskytningsmidler så som TBTO (tributyltinoksyd), PCP (penta-klorofenol) og Diklorofluanid. The activity of the compound is very high, not only in comparison with the activity of other known plant pathogenic fungicides, many of which are not at all effective against wood-producing fungi, but also in comparison with the activity of well-known and widely used wood preservatives such as TBTO (tributyl tin oxide), PCP (penta- chlorophenol) and Dichlorofluanid.
Anvendelsen, ifølge oppfinnelsen består i å bringe tre i kon- The application, according to the invention, consists in bringing wood into con-
takt med anilidet. Forbindelsen N— (1,1,2, 2-tetrakloro-2-fluoroetyltioj_-metansulfonanilid kan anvendes i en hvilken som helst av de væsker som vanligvis anvendes som oppløs-ningsmiddel ved fremstilling av trebeskyttelsesmidler. Eksempelvis kan nevnes en blanding bestående av 4 % av den nevnte forbindelse, 9 % av et alkydbindemiddel eller linolje og 87 % av et flytende aromatisk hydrokarbon eller blanding av slike. Den spesielle sammensetning som er å foretrekke er avhengig av forskjellige faktorer, såsom tresorten, graden av den ønskede beskyttelse og den anvendte fremgangsmåte ved impregnering av treet. tact with the anilide. The compound N-(1,1,2,2-tetrachloro-2-fluoroethylthioj_-methanesulfonanilide) can be used in any of the liquids that are usually used as a solvent in the production of wood preservatives. For example, a mixture consisting of 4% of said compound, 9% of an alkyd binder or linseed oil and 87% of a liquid aromatic hydrocarbon or mixture thereof. The particular composition which is preferred depends on various factors, such as the type of wood, the degree of protection desired and the method used by impregnating the wood.
En fagmann vil uten vanskelighet i hvert enkelt tilfelle A professional will without difficulty in each individual case
kunne avgjøre hvilken spesiell sammensetning som bør anvendes og den påføringsmåte som er å foretrekke i det aktuelle tilfelle. be able to decide which particular composition should be used and the method of application which is preferable in the relevant case.
Oppfinnelsen illustreres ved de folgende eksempler som viser effekten av middelet mot den treodeleggende sopp Coniphora cerebella. For å vise denne effekt anvendes to forskjellige prøvemetoder. The invention is illustrated by the following examples which show the effect of the agent against the wood-destroying fungus Coniphora cerebella. To show this effect, two different test methods are used.
Metode 1.: Method 1.:
3 3 3 Provestykker av furutre med dimensjonene 7 cm x 1,6 cm x 0,2 cm torkes i 24 timer ved 103°C, hvoretter de veies. 3 3 3 Test pieces of pine wood with the dimensions 7 cm x 1.6 cm x 0.2 cm are dried for 24 hours at 103°C, after which they are weighed.
Forbindelsen som skal undersokes fremstilles i en konsentrasjons-serie på 4, 2, 1, 0,5, 0,25, og 0,125 % opplost i etylacetat inneholdende 9 % av et alkydbindemiddel. The compound to be examined is prepared in a concentration series of 4, 2, 1, 0.5, 0.25, and 0.125% dissolved in ethyl acetate containing 9% of an alkyd binder.
Impregneringen av provestykket foretas ved å neddyppe disse i opplosningen i en kort tid. Vektopptakelsen skal være ca..100 kg The test piece is impregnated by immersing it in the solution for a short time. The weight intake must be approx. 100 kg
3 3
opplosning pr. m tre. resolution per m three.
Etter torking i to dogn ved romtemperatur pakkes prøvestykkene inn i steramidposer, som varmeforsegles og steriliseres ved bestråling, fortrinnsvis U. V. eller gammastråling. After drying for two days at room temperature, the test pieces are packed in steramide bags, which are heat-sealed and sterilized by irradiation, preferably UV or gamma radiation.
Glasskrukker inneholdende 500 ml jord spesielt gjodslet med hen-blikk på vekst av Coniophora cerebella steriliseres ved opp-varmning i et oklaver i 3 timer ved 120°C og avkjoles deretter til romtemperatur. Provestykkene anbringes i sterile krukker og jorden podes med et mycelium av Coniophora cerebella. Deretter henstilles krukkene i 4 uker ved 22°C og 70 % R F. Glass jars containing 500 ml of soil specially fertilized with a view to the growth of Coniophora cerebella are sterilized by heating in an oven for 3 hours at 120°C and then cooled to room temperature. The samples are placed in sterile jars and the soil is inoculated with a mycelium of Coniophora cerebella. The jars are then stored for 4 weeks at 22°C and 70% R F.
Etter denne periode uttaes provelegemene, borstes omhyggelig fri for jord, torkes ved 103°C og veies. Vekttapet beregnes i % av den opprinnelige vekt. After this period, the test specimens are removed, carefully brushed free of soil, dried at 103°C and weighed. The weight loss is calculated in % of the original weight.
Metode 2.; Method 2.;
Provestykker av bok og furu impregneres omhyggelig med en O,25 % opplosning av den forbindelse som skal undersokes, hvoretter provestykkene innfores i usterilisert standard-jord og for å henstå ved 22°C og 90 % R F. Test pieces of beech and pine are carefully impregnated with a 0.25% solution of the compound to be examined, after which the test pieces are introduced into unsterilized standard soil and left to stand at 22°C and 90% R F.
Etter 12 ukers henstand taes provelegemeene ut, renses og torkes, hvorettér vekttapet beregnes i % av den opprinnelige vekt. After a 12-week grace period, the test specimens are taken out, cleaned and dried, after which the weight loss is calculated as a % of the original weight.
Eksempel 1 Example 1
Sammenligning med kjente trebeskyttelsesmidler. Comparison with known wood preservatives.
Ved anvendelse av metode 1 undersokes de folgende forbindelser When using method 1, the following compounds are examined
A. ;, N- (1,1, 2, 2-tetrakloro-2-f luoroetyltio) -metansulfonanilid. A. ;, N-(1,1,2,2-tetrachloro-2-fluoroethylthio)-methanesulfonanilide.
B. PCP + abietylamin (molforhold 1:1) B. PCP + abiethylamine (molar ratio 1:1)
C. PCP + TBTO (molforhold 1:1) C. PCP + TBTO (molar ratio 1:1)
D. Diklbfluanid D. Diklbfluanide
E. 2,2-diklor-l,4-naphtoquinon E. 2,2-dichloro-1,4-naphthoquinone
Ekse mpel 2. Example 2.
Sammenligning med kjente plantepatogene fungicider. Comparison with known plant pathogenic fungicides.
Ved bruk av metode 1 undersokes folgende forbindelser. When using method 1, the following compounds are investigated.
A. "Folpet" A. "Folpet"
B. "Captan" C. "Diklofluanid" D. "Difolatan" E. "Benomyl" F. "Thiabendazole" G. N-(1,1,2,2-tetrakloro-2-fluoroetyltio)-metansulfonanilid B. "Captan" C. "Diclofluanid" D. "Difolatan" E. "Benomyl" F. "Thiabendazole" G. N-(1,1,2,2-tetrachloro-2-fluoroethylthio)-methanesulfonanilide
Eksempel 3 Example 3
Sammenligning med kjente trebeskyttelsesmidler. Comparison with known wood preservatives.
Ved anvendelse av metode 2 undersokes i dé i eksempel 1 nevnte forbindelser. Det eneste provestykket uten synlig tegn på mikrobiologiske angrep og som ikke viste noe vekttap var de som var impregnert med N-(1,1,2,2-ettrakloro-2-fluoroetyltio)-metansulfonanilid. Alle de andre provestykker viste et vekttap fra ca. 12% til mere enn 20%. When using method 2, the compounds mentioned in example 1 are investigated. The only sample without visible signs of microbiological attack and which showed no weight loss were those impregnated with N-(1,1,2,2-tetrachloro-2-fluoroethylthio)-methanesulfonanilide. All the other test pieces showed a weight loss from approx. 12% to more than 20%.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB17019/75A GB1528041A (en) | 1975-04-24 | 1975-04-24 | Process and composition for the treatment of wood |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO761398L NO761398L (en) | 1976-10-26 |
| NO145605B true NO145605B (en) | 1982-01-18 |
| NO145605C NO145605C (en) | 1982-04-28 |
Family
ID=10087762
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO761398A NO145605C (en) | 1975-04-24 | 1976-04-23 | USE OF N- (1,1,2,2-TETRACHLORO-2-FLUORETHYLTIO) -METHANE SULPHONANILIDE TO FIGHT AGAINST CONIOPHORA CEREBELLA IN THREE |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS51130506A (en) |
| AU (1) | AU499840B2 (en) |
| BE (1) | BE840880A (en) |
| BR (1) | BR7602501A (en) |
| CA (1) | CA1075099A (en) |
| CH (1) | CH622207A5 (en) |
| DE (1) | DE2616682A1 (en) |
| DK (1) | DK136808B (en) |
| FR (1) | FR2308476A1 (en) |
| GB (1) | GB1528041A (en) |
| NL (1) | NL7604248A (en) |
| NO (1) | NO145605C (en) |
| NZ (1) | NZ180668A (en) |
| SE (1) | SE410158B (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT296253B (en) * | 1967-10-05 | 1972-02-10 | Stauffer Chemical Co | Process for the preparation of new N-substituted 2-fluoro-1,1,2,2-tetrachloroethanesulfenic acid amides |
-
1975
- 1975-04-24 GB GB17019/75A patent/GB1528041A/en not_active Expired
-
1976
- 1976-03-29 DK DK137876AA patent/DK136808B/en unknown
- 1976-04-15 DE DE19762616682 patent/DE2616682A1/en not_active Withdrawn
- 1976-04-16 BE BE166263A patent/BE840880A/en unknown
- 1976-04-19 JP JP51043803A patent/JPS51130506A/en active Pending
- 1976-04-20 CA CA250,447A patent/CA1075099A/en not_active Expired
- 1976-04-22 AU AU13256/76A patent/AU499840B2/en not_active Expired
- 1976-04-22 NL NL7604248A patent/NL7604248A/en not_active Application Discontinuation
- 1976-04-23 NO NO761398A patent/NO145605C/en unknown
- 1976-04-23 FR FR7612036A patent/FR2308476A1/en active Granted
- 1976-04-23 CH CH514576A patent/CH622207A5/en not_active IP Right Cessation
- 1976-04-23 BR BR2501/76A patent/BR7602501A/en unknown
- 1976-04-23 SE SE7604704A patent/SE410158B/en unknown
- 1976-04-23 NZ NZ180668A patent/NZ180668A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR7602501A (en) | 1976-10-19 |
| CA1075099A (en) | 1980-04-08 |
| DE2616682A1 (en) | 1976-11-11 |
| NO145605C (en) | 1982-04-28 |
| DK137876A (en) | 1976-10-25 |
| SE7604704L (en) | 1976-10-25 |
| FR2308476A1 (en) | 1976-11-19 |
| DK136808B (en) | 1977-11-28 |
| CH622207A5 (en) | 1981-03-31 |
| FR2308476B1 (en) | 1978-05-19 |
| JPS51130506A (en) | 1976-11-12 |
| NZ180668A (en) | 1978-04-03 |
| AU499840B2 (en) | 1979-05-03 |
| SE410158B (en) | 1979-10-01 |
| BE840880A (en) | 1976-08-16 |
| NL7604248A (en) | 1976-10-26 |
| GB1528041A (en) | 1978-10-11 |
| DK136808C (en) | 1978-05-08 |
| AU1325676A (en) | 1977-10-27 |
| NO761398L (en) | 1976-10-26 |
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