3-ISOTHIAZOLONE INSECTICIDES

Abstract: 3-Isothiazolone of the formula wherein R and R¹ are the same or different radicals selected from hydrogen, halo or C₁₋₄ alkyl and Y is substi­ tuted or unsubstituted (C₁₋₁₈) alkyl wherein the substituent is selected from hydroxy, halo, cyano, alkylamino, dialkyla­ mino, phenylamino, halophenylamino, carboxy, carbalkoxy, alkoxy, aryloxy or carbamoxy, substituted or unsubstituted aryl, substituted or unsubstituted aralkyl or unsubstituted or substituted cycloalkyl having 3 to 6 nuclear carbon atoms or a salt thereof are useful in killing or repelling certain wood destroying pests, especially termites.

Description: 3-ISOTHIAZOLONE INSECTICIDES This invention relates to a method of using 3isothiazolones or salts thereof to combat pests such as insects or their larvae. Examples of insects which can be repelled are subterranean termites (Termitidae), drywood termites (Kalotermitadae), moist wood termites (Rhinotermitidae), damp wood termites (Termopsidae) marine moluscan borers (Limnoria), crustacean borers (Teredo), Scolytid beetles, Platypodid beetles, Lyctid beetles, Anobid beetles and the like. The method of this invention is especially useful to protect wood against such insects or their larvae. Of particular interest is the combatting of attack by furniture beetle, elm borer or death watch beetle. There are three general classes of wood preservatives, toxic oils such as creosote that evaporate slowly and are relatively insoluble in water; water solutions of salts that are injected directly into the wood, and finally, highly toxic chemicals which are normally dissolved in solvents or mixtures of solvents other than water. This invention employs known 3-isothiazolone biocides. Patents disclosing 3-isothiazolones, their preparation and their uses include U.S. Patents Nos. 3,523,121; 3,761,488; 3,887,352; 4,062,946; 4,105,432; 4,127,687; 4,150,026; 4,241,214; 4,243,403; 4,252,694; and 4,279,762. These compounds are especially effective in preventing damage to wood caused by wood attacking insects. The 3-isothiazolones can be incorporated into the wood by any of several methods including pressure impregnation, vacuum impregnation, dip treatment, spray treatment, application of a gel or paste or application of a dust. The compounds are especially useful against termites and can also be used against marine molluscan borers, crustacean borers, Scolytid beetles, Platypodid beetles, Lyctid beetles, Anobid beetles and the like. The 3-isothiazolones which may be employed in this invention have the following structural formula: EMI2.1 wherein R and R1 are the same or different radicals selected from hydrogen, halo or C1-C4 alkyl and Y is substituted or unsubstituted (C118)alkyl wherein the substituent is selected from hydroxy, halo, cyano, alkylamino, dialkylamino, phenylamino, halophenylamino, carboxy, carbalkoxy, alkoxy, aryloxy or carbamoxy, Y can also be substituted or unsubstituted aryl, substituted or unsubstituted aralkyl or unsubstituted or substituted cycloalkyl having 3 to 6 nuclear carbon atoms or a salt thereof. Especially preferred are those compounds where R and R1 are hydrogen and Y is selected from C1-C12 straight- or branched-chain alkyl, benzyl, -chlorobenzyl, phenethyl and E-chlorophenethyl; also those where R and R1 are chloro and Y is selected from C1-C12 straight- or branched- chain alkyl, benzyl, ±-chlorobenzyl, phenethyl and g-chloro- phenethyl and cyclohexyl; also, where R is methyl, 1 its chloro and Y is phenyl and substituted phenyls; and where R is hydrogen, R2 is chloro and Y is selected from C1-C;2 straight or branched chain alkyl, benzyl, Erchlorobenzyl, phenethyl and ±-chlorophenethyl and cyclohexyl. In addition to treating the wood directly with 3isothiazolones, the material may be applied directly to the wood destroying insects. When it is desired to treat the wood directly, the 3-isothiazolones will be applied to give a retention of from about 0.001 to about 1.0, and, preferably, from about 0.01 lbs. to about 0.5 lbs. of isothiazolones per cubic foot of wood. When it is desired to spray the wood destroying insects directly, including treating infested wood, the effective amount of 3-isothiazolone applied is generally in the range of from about 0.01% to about 20% by weight of active ingredient and, preferably, from about 0.10 to 2.5% by weight of active ingredient. Suitable solvents which may be employed as vehicles include water, mineral spirits, toluene, xylene, acetone, kerosene, aromatic hydrocarbons, benzene, ethyl acetate, white spirits and the like. The 3-isothiazolones can be used alone or may be blended with other wood preserving materials such as creosote, pentachlorophenyl, copper-chromearsenic, tributyl tin oxide, copper-8-quinolinolate, copper naphthenate, methylene bisthiocyanate, chlorothalonil, 2-(thiocyanomethylthio) benzothiozol, 3-iodo-2-propynyl butyl carbamate, N-nitroso-N-cyclohexyl hydroxylamine, N-cyclohexyl-Nmethoxy-2,5-dimethyl-3-furamide, benzimidazolyl methylcarbamate, sodium pentachlorophenate, sodium tetrachlorophenate and similar known materials. The following test data shows the activity of two of the 3-isothiazolones; however, it is to be understood, that by substituting other 3-isothiazolones or salts thereof, similar results would be obtained. EXAMPLE 1 This test (TABLE I) shows the termiticide activity of 5-chloro-N-methyl-3-isothiazolone in terms of percent survivors. The test is conducted by placing termites onto filter paper which had been dip treated with the various concentrations of the test compound and counting survivors over time. Termites: Reticulitermes spp. collected from rotted logs. 50 adults were used for each sample. Method: Solutions of the test compound were prepared at concentrations ranging from 0.01% active ingredient to 3.0% active ingredient. Filter paper discs (9.0 cm Whatman No. 2) were dipped into the test solutions, removed and allowed to dry at room temperature. Dried filter papers were placed into Petri dishes and 50 adult termites were added. After various amounts of time the number of live termites were counted. The following table shows the results of the test: TABLE I 5-chloro-N-methyl- 8 Survivors 3-isothiazolone Initial 5 Hours 1 Day 2 Days 3 Days 4 Days (t percent active ingredient) 0.0 100 100 100 98 96 94 0.01 100 75 54 0 0 0 0.05 100 51 13 0 0 0 0.10 100 38 0 0 0 0 0.20 100 34 0 0 0 0 0.30 100 32 0 0 0 0 0.50 100 41 0 0 0 0 1.0 100 5 0 0 0 0 2.0 100 0 0 0 0 0 3.0 100 0 0 0 0 0 This test (TABLE II) is performed following the ASTM D3345-74 Termite Test employing 4,5-dichloro-2-N-octyl-3isothiazolone. Southern yellow pine blocks were vacuum impregnated with the isothiazolone. The blocks were then exposed to Reticulitermes flavipes termites. TABLE II Retention of isothiazolone in 1 2 pounds per Weight Block cubic foot Loss % Rating Mortality 0.0 8.9 4.0 Slight 0.003 3.6 5.8 Complete 0.016 1.6 9.0 Complete 0.030 0.1 9.8 Complete 0.078 0.0 10.0 Complete 0.161 0.0 10.0 Complete 1) Values are averages of five replicate wood blocks 2) Ratings: 10 = Sound surface, slight nibbles 9 = Light attack 7 = Medium Attack 4 = Heavy attack 0 = Total failure The above data illustrates the effectiveness of the isothiazolones in killing and repelling wood destroying insects. It is to be understood that changes in variations may be made without departing from the spirit and scope of the invention as defined by the following claims.

Claims: CLAIMS: 1. A method for combatting wood destroying pests which comprises incorporating into wood and/or contacting the pests with an effective amount of an isothiazolone bf the formula: EMI7.1 where R and R1 are the same or different radicals selected from hydrogen, halo or C14 alkyl and Y is substituted or unsubstituted (C1 18)alkyl wherein the substituent is selected from hydroxy, halo, cyano, alkylamino, dialkylamino, phenylamino, halophenylamino, carboxy, carbalkoxy, alkoxy, aryloxy or carbamoxy, substituted or unsubstituted aryl, substituted or unsubstituted aralkyl or unsubstituted or substituted cycloalkyl having 3 to 6 nuclear carbon atoms or a salt thereof. 2. A methpd of claim 1 wherein the isothiazolone or salt thereof is incorporated into the wood in an amount of from 0.001 to 1.0 pounds per cubic foot of wood preferably 0.01 to 0.5 pounds per cubic foot of wood. 3. A method of any preceding claim wherein Y is an unsubstituted alkyl group of 1 to 18 carbon atoms and/or R is hydrogen and/or R' is hydrogen or halogen. 4. A method of claim 3 wherein R is hydrogen and/or R1 is hydrogen or halogen. 5. A method of claim 3 wherein R' is hydrogen or halogen. 6. The method of any preceding claim wherein Y is a n-octyl, R is hydrogen and R' is hydrogen or wherein Y is methyl, R is hydrogen and R' is chlorine. 7. A method of any preceding claim wherein the isothiazolone is used in a composition containing 0.1% to 20% by weight of the isothiazolone. 8. A method of any preceding claim wherein the wood destroying pest is subterranean termite, dry wood termite, moist wood termite, damp wood termite, marine molluscan borer, crustacean borer, Scolytid beetle, Platypodid beetle, Lyctid beetle or Anobid beetle.

Inventors: GREENLEY, DAVID EUGENE
Applicants: ROHM AND HAAS COMPANY
Application year: 1985
Main classification: A01N43
IPC codes: A01N43, B27K3