CA1043700A - Terpenylamino alkanol fish toxicants - Google Patents

Abstract

ABSTRACT OF THE DISCLOSURE

Terpenylaminoalkanol compounds and their acid salts, having the formula:

wherein T is a radical selected from the group consisting of geranyl, citronellyl, bupleuryl, neryl, lavandulyl, linalyl, myrcenyl, isobornyl and tetrahydrogeranyl;
R is independently hydrogen or C1-4; and x is an integer from 1 to 4.

Description

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Thi~ invention relates to new pi~cicide~. Although several general fish toxicants are known there iR a great need for agents which will selectively control undesirable ~pecies of fish without harmful effect on desirable ~pecie~
S present in the same body of water. The common carp is known to be destructive of the habitat of desirable game fish and consequen~ly there ls a particular need for oontrolling carp populations. Presently there are two important registered ~` fish toxicants which are widely u~ed to kill carp and o~her species of ish -- Rotenone and antimycin. ~hese toxicants suf~er from the disad~antages that they are non-selective for carp and their aativi~y iB adversely a~fected by water~ of high p~.
The present invention provides a selective fish lS ~oxicant for controlling fish populations comprising a ~ ;
carr~ar and an effective amount of about 20-95 per cent by weight of certain terpenylaminoalkanol ~ompounds and deri-~at~ve~ t~ereof.
This invention also provi~es a proces~ for treat-

2~ ing ponds and other bodies of water whereby tra~h fish popu--~ lations can be controlled or eliminated without Qubstantial . ::
~ injury to other desirable fish, including game fish, by treat-i ing such water with an effecti~e amount of about ~.03 to 1.5 parts per million of certain terphenylaminoalkanol compounds, their acid salts and certain ~uaternary salt derivatives ~2-~q~
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thereof.
Further a piscicide i9 provided that i~ compatiblewith nature and will readily deactivate, detoxify and be sub-~: stantially innocuous to other organisms indigent to such bodies of water. Also, a pisaicide and proce~ for the con-~ trol of carp i 9 provided.
:; The term 'piscicide' refers to a toxicant or chemiaal that when applied to the water habitat of fish tends to poison and otherwise control the population of certain fish, especially trash fish, while being innocuous toward other desirable fish species.
The terphenylaminoalkanols of this invention can be repre~ented by the Formula I:
. T \ R~ R
`s / N - C - C - OH :
:~ ~ ~ x ~ ... I -H) L5 wherein:
is a radical selected from the group consisting of acyclia monoterpenyl, isobornyl and tetrahydrogeranyl R is independently hydrogen or a lower alkyl radical-containing 1 to 4 carbon; and .
;.~ 20 x is an integer o~ ~rom 1 to 4.
- ~ The acyolic monoterpenyl radicals falling within the scope of the above Formula include citronellyl, bupleuxyl, .~. geranyl, neryl, lavandulyl, linalyl, and myrcenyl. Advan-. tageous and pre$erred sele~tive toxicant compounds are those. ~ :
. :~
wherein T represents geranyl, meryl and linalyl. Espeoially pxeferred toxi~ants are the diterpenylaminoalkanols for ex-: ample, N-(2-hydroxyethyl) digeranylamine and N-(3-hydroxy-propyl) digeranylamine.

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Further groups representative of T in Formula I
above include partially and fully hydrogenated acyclic mono-~; terpenyl groups and the isobornyl group. Preferred within this sub-group are the mono and di(3,7-dimethyloctyl) toxic-~; 5 ants derived from geranyl and/or linalyl aminoalkanols.
Especially preferred are the compounds N-(2-hydroxyethyl) di(3,7-dimethyloctyl)amine and N-(2-hydroxyethyl)diisobornyl-` amine.
:
~ Compounds falling within the scope of the above ; 10 Formula have limited water solubility but can be mada water-soluble by converting them into corresponding ammonium salts (or ~ertiary amine ~alts) by reacting them with an appropriate ; acid. Acids useful for preparing ~he acid-addi~ion salts include inorganic acids, such as hydrohalic acids (e.g., , hydrochloric and hydrobromic), sulfuric acid, nitri¢ acid, `; and pho~phoric acid and organic acids such as oxalio, maleic, ~ tartaric, citric, acetic and succinio acid. Such acid salts ;~ ~ are readily soluble in water and can be formulated in water ~`- for appliaation to the ponds and/or other aqua~ic area fish habitats. It is contemplated that both the hydroxyalkylamine and their water-soluble salts will be useful in tha practice ~ ` of this invention.
-~ Praferred salts are hydrohalide salts, ~or example, the hydrochloride and hydrobromide salts. These salt are conveniently formed from readily a~ailable hydrogen chloride and hydrogen bromide gases or from aqueou~ acid solution~
When the anhydrous salt is desired it may be prepared by add-ing a stoichiometric amount o~ an anhydrous ether solution of the hydrogen halide to an ether solution of the appropriate terponylamin~alkanol. rhe amine hydrohalide (or aoid salt) , , ~, . .
, ~O~ 3~

usually forms as a white solid which can be filtered and further purified by recry tallization. Commercially it will u~ually be more feasible to react the terpenylaminoalkanol with ~he stoichiometric amount of the desired aqueouR acid to form an a~uaous solution of the salt which may be con-veniently diluted urther with water to the desired con-centration for storage and ~hipment. It is preferred to prepare salt solution~ of the order of 20-75 per cent by weight active toxicant since these appear more skable over : 10 prolonged periodq of storage. Especially pre~erred are solu-tions o~ about 50 weight per cent toxicant.
It is also within the scope of the invention to use quaternary salts of the desired terpenylaminoalkanol in place of the acid salts described above. Thus a wide variety of salts having water solubility greater than the free aminoalkanol are provided. The preparation of quaternary :.
salts is well-known. ~hey are synthesized in a procedure similar to ~he anhydrous acids salts with the exception that a reactive Cl_l2 hydrocarbyl halide is u~ed in place of the hydrogen halide. Simple quaternary salts may be made ~rom methyl and ekhyl bromide. Preferred quaternary salts are tho~e prepared by the reaction of terpenylaminoalkanol with ,,. O
allyl bromide or ohloride, gerany- bromide or chloride, benzyl halides and naphthyl halides. ~he quaternary salt prepared ~, 25 from myrcenyl chloride is especially preferred because of lt~
i availability and ~he desirable propertie~ of ~he re~ulting salt~
The ~ree aminoalkanolq and their salts may be further formulated with aonventional carriers and di3persing j~ 30 agents to meet the various conditions of climat~, water S- '' ' : ' ; .
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temperature, alkalinity, acidity and hardness of the treated water. In general where the water is acidic it is desirable to use ~he ~ree amine or the quaternary salt; when the water i5 basic all three forms of the terpenylaminoalkanol toxicant - 5 or mixture~ ~hereo may be used. In general the best formula-tion will be determined by the characteris~ics of the water to be treated. When the free terpenylaminoalkanol is used it can be dissolved or dispersed in typical liquid aarriers 7 commercially available alcohols are sa~isfaotory; dispersions in inert hydrocarbon diluents can be used where conditions permit. Common we~ing agen~ and surfactant~ may be used to obtain uniform compositions of the order of 20-95% active : toxicant. When the toxicant chosen is the aaid or quaternary salt og the aminoalkanol, it i8 usually preferred for economi-cal reasons to dissolve or disperse these in water.
Typical solid carriers on which the terpenylamino-alkanols may be deposited include finely divided inorganic solid materials, siliceous minerals, clays, bentonite, atta-pulg~te, fullers earth, diatomaceous earth, kaolin, mica and talc as well a other prepared siliceous materials including sil~ca gels, aerogels and fume cilicas. When solid carriers are used basic clays are generally preferred~ especially when the pH of the pond water is on the acid side. These composi-tions help to prevent rapid deterioration of the active ter- -`
penylaminoalkanol.
Application doses of the active aminoalkanols o this invention and their inorganic acid salt~ sultably are from 0.03 to 10 parts per million parts of water ~reated.
0~ course, these quantities will vary somewhat depending on the particular characteristics of the water. Specific . _ _ '7~
factors including the presence of particular microorganisms will effect the optimum quantity of toxicant to be used.
TreatmenY~ lower than about 0.03 parts per million will gener-ally be insufficient to control the trash fish whila concen-tration~ of ~oxicant above 2.0 parts per million usually will be toxic bo~h to the deslrable ~peoias as well as to the trash fish and should be avoided when selectivity is desired. It is preerred to treat the ponds and other bodies of water to be protected with incremental amounts of the toxicant over a period of 1-3 days gradually building up the conaentration of ac~ive ~erpenylaminoalkanol to the optimum value. The present tox~cants usually ar~ effec~ive in about 10-100 hour~ a~ter treatment of the water i9 made.
The partiaular hydrocarbyl aminoa:lkanols o thi~ invention are eaologically desirableY; laboratory studies show these aminoalkanols deactivate within about seven days.
It is preerred to name the toxicants of this in-vention as amineæ rather than alcohols. However, it would not be incorrect to use nomenclature where the alcohol portion is treated as the principal funation. In this manner the above compounds would be also correctly identified as di(3,7-dimethyloctyl) aminoethanol and 2-~diisobornyl) amino-ethanol, respectively.
Advantageous alkanol groups in Formula I are primary, secondary and tertiary alkanol groups containing between 2 and 8 carbon atom~ and include those radicals derived by removing a hydrogen atom from an unhydroxylate~
y carbon a~om from ethanol, n-propanol, 2-methyl~2-propan~
2-methyl-1-propanol, n-butanol, isobutan~l, tertiary ~utyl r 30 alcohol, and the various normal isomeric pentanols, hexanols, :, ' ' .~ ',.:- ~ . ' ' .

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heptanols and octanols. Although tertiary al ohol~ and secondary alcohols are useful fish toxicants, piscicides having the primary alcohol structure~ ara preferred. Especial-ly preferred are ethanols and ~ubRti~uted ethanols wherein the terpenylami~o function is separated from the hydroxy group by two aarbon atom~.
Speoi~ic compounds which are tertiary amines and whiah are useul in the practice of this invention include the ollowing compounds and their citronellyl, and linalyl counterparts:
N-(3-hydroxypropyl) digeranylamine N~ methyl-2-hydroxyethyl) digeranylamine N-(l,l-dimethyl-2-hydroxyethyl) digeranylamine N-tl-ethyl-2-hydroxyethyl) digeranylamine N-~2-hydroxyethyl) digeranylamine N (5-hydroxypentyl) digeranylamine N-~3~hydroxybutyl) digeranylalmine N-(l-ethyl-2-hydroxyethyl) di(3,7-dimethyloctyl)amine N-(5-hydroxypentyl)digeranylamine N-(3-hydroxypropyl) digeranylamine N-(2-hydroxyethyl) di(3,7-dimethyloctyl)ami.ne N-~2-hydroxyethyl) dilsobornylamine Specific compounds which are secondaLy amlnes and ~. , which are useful in the practice of this invention include the following:
N-(3-hy~roxypropyl) geranylamine N-(2-hydroxypropyl) linalylamine N-(I,l-dimethyl-2-hydroxyethyl) aitronellylamine N-tl-ethyl-2-hydroxyethyl) lavandulylamine N-(3-hydroxybutyl) bupleurylamine ~L~3~
N-(5-hydroxypen~yl) nerylamine N-(2-hydroxyethyl) 3,7-dime~hyloctylamine N-(l-methyl-2-hydroxyethyl) isobornylamine The compounds of thi~ invention may be prepared by modification of methods well-known in the li~erature. Common general method~ for the preparation of substituted amino-alkanol~ are shown in United ~tates Patent No. 2,36~,081 a~
intermediates for the preparation of various local ane~.he~i~
esters and in the Journal of the American Chemical Society publications by Ringk et al ~65 p. 1222, 1943), Cope et al (66 pp. 1733-1747, 1944), Piexce et al t71 p. 1~65, 1949).
Other synthetic approaahes oacasionally used include prepara-tion o the corresponding amino ketone followed by reduction o the ke~o group to yield the de~ired alcohol and hydrogen-ation of the correspondign oxazolidines. .
A pre~erred synthetic me~-hod for the preparation o~ the aompound~ of this invantion aomprises heating the corresponding hydrocarbyl halide with the hydroxy lower alkyl-amine-s such as1 for exampls, 2-hydroxy-1,1-dimethylethylamin~
and 3-hydroxy-propylamine at a temperature in the range ~rom 40~C. to 160C. in the pre~ence o~ an acid acceptor. If desired, an excess of the lower hydroxyalkyl amine aan be .
used as the acid acceptor. Thr reaction i~ preferably ~arried out in an organic sol~ent inert under the condition3 of ~he raac~ion. For example, methanol, ethanol, propanol ;-and higher alcohol and ether~ may be u~ed but hydrocarbons ~uch a~ ben~ene, xylene and the like are generally prefarred.
~he acid acceptor generally is a basic substanae which fo~ms water-solubla by-products salts with the ~volved hydrogen ha~ide and includes both inoryanic matal hydroxide and .~9_ :

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~3~7(~
tertiary amines quch as triethylamine and pyridine. When a hydrocarbon solvent i3 used, the by-product amine hydro-chloride will be an insoluble solid which can be easily ~eparated from ~he reaction product by filtration. Work-up i~ conveniently carried out by filtering the amine hydro-¢hloride, washing the organic phase with water, evaporating the solvent and distilling the product. In some ca~es where the produc~s are solids recrystallization is preferred to distillation.

Commercial myrcenè hydrochloride, 290 grams (1.12 moles con~aining abou~ 67~ by weight usable geranyl and neryl chlorides) was slowly added with stirring over a four hour period to 220 grams ~2.25 moles) of molten 2-amino-2-methyl-l-propanol maintained at 55-65C., and the ~tirring was con-tinued at this temperature for an additional 2-1/2 hours after completion of the addition. The reaction mixture was made alkaline with 20% aqueous sodium hydroxide and further heated under reflux for one hour. After cooling, the organic oil was ~eparated, washed with water, and dried with anhydrous magnesium sulfate. The oil was distilled ~nder vac,um through a short Vigreaux column and the fraction ~oiling over the range 100-125C. at 0.07 mm Hg absolute was collected and identified as 99~ pure N-(2-hydroxy-1,1-dimethylethyl) geranyl~
amine (41% yi~ld). NMR spectroscopy identified the product as a mixture containing both the geranyl and neryl i~omers.

N ~
The vacuum distillation descri~ed in Ex~mple 1 was ~()437~
continued after removing the monogeranylamine. After dis-carding an intermediate fraction N-(2-hydroxy-1,1-dimethyl-Pthyl) digeranylamine was isola~ed in 21% yield. b.p. 170-190 a~ 0.07 mm ~g absolute. NMR spectroscopy showed this fraction to be 98~ pure tmixture of geranyl and neryl iso-mers).

A solution of 20 grams of N-~2-hydroxy~ di-methylethyl)ger~nylamine in 25 milliliters of glacial acatia acid was treated with 0.4 grams of platinum oxide ~"Adams Catalyst") and subjected to hydrogenation at 80 pYi hydrogen pressure for three hours. The resultant solution was filter-ed to rem~ve the catalyst, diluted with aqueous sodium hydr-oxide and the crude product was allowed to solidify. When recrystallized from aaetone a whi~e solid was obtained meet-ing 59-61C. Alternatively, purification could be effected by disti}lation under reduced pres~ure (b.p. 108-155C. at 0.17 mm Hg absolute). The structure of the produet was verified by NMR spectroscopy.

N-(2-hydrox~ethyl) geranylamine was prepared in a -manner similar to ~he procedure of Example 1 except that the alcohol used was 2-aminoethanol.
~XAMP~P S
N-(2-hydroxyethyl) digeranylamine was prepare~ in a manner similar to the procedure described in Examples 1 and 2. Distillation under vacuum was continued af~er isolating the aompound described in Example 4 and to give the product ~;
which was a liquid, b.p. 170-175C. a~ 0.2 mm Hg absolute;

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4~7~) MD(25) 1.496; sp. gr. 0.870/20C.

N-~2-hydroxypropyl) geranylamine was prepared in a ma~ner similar to the procedure of Examples 1 and 2 except that amino alcohol used was 2-hydroxypropylamine. N- (2-hydr-oxypropyl~ digeranylamine was obtained as a higher boiling fraction.

N-(l-hydroxymethylpropyl) ~i(3,7-dimethyIoctyl) amine was prepared in a manner similar to the procedure of Example 3 except that the starting material used was N-(l-hydroxymethylpropyl) digeranylamine.

N-(2-hydroxyethyl) digeranylamine was tested as a selective fish toxicant in outdoor pools ~toaked wi~h various fish species and lined with black plastic using 50~
wa~er-soluble formulations (hydrochloride salt). The formu-lation was added to each of four pools of 4,000-liter capacity at concentrations of 0.10, 0.15, 0.20 and 0.30 mg./liter.
Another pool containin~ the same number, ~ize and species of fish served as a control. The test water had algal blooms, a pH o~ about 8.5 and a total hardness of about 200 mg./liter as CaCo3. The temperature was cool enough ~15-16C.) to per-mit- the use of trout.
Fish were obtained fxom state and federal hatcherie~
; and maintained prior to testiny by a tralned fish culturist.Fish of t~tal length 2-5 cm. were used in laboratory tests -~
while for outdoor tests sma}l fish (4-B cm~ in length) and larger carp and buffalo tIctlobus cyprinellus) were used.

3~ In all ~ests 10 fish of each spe~ies were exposed 3i7~1~

to ~elective concen~rations of the toxiaant. Mortalitie~
were obsQrvad and xecorded at 1.2 and 6 hours on the first day and once daily therea~ter, during 96 hour exposure.
Laboratory test~ were al50 conducted in sof~ water 12C. wherein the toxicant was evaluated against fifteen species of fish in~luding both aold and warm water vari~ties. ~:In Table 1, the LC 50 toxicity values for N-(2-hydroxye~hyl) :~
digeranylamine is shown for various species. LC 50 i~ de-fined as the amount (mg./liter) of toxicant required to kill 50 p~r cènt at 95% aonfidence interval. ~hus, the 96 hour LC 50 agains~ carp is O.OS0 mg.~liter as compared ~o 0.37 for smallmouth bass and 0.72 for bluegill. Chinook, coho salmon, rainbow trout, goldfi h, fathead, minnow, banded .
killfish and walleye were more resistant to the toxicant than carp or white suckers.
EX~MPLE 9 . _ :
~he sffect o the various toxicants o~ common : :
invartebrate species waY determined in a static test con~
ducted 17C. Tho invertebrat~s tested were collected from j 20 natural population9 or purcha~ed from commercial suppliers. -~
~hey were held in soft water in fiberglass tanks in the labora~ory or in outdoor plastic swimming pool s . Mortality was observed during holding, and only healthy organi ms were used for the toxiaity ~ests. At least 10 organi~m~ of nine . 25 species were exposed to each aoncentration in static tests.
Tubifex was by far the most sensitive species and the LC 50 (0.054) i9 signifioantly different from LC 50's for the toxicant or other ~pecies tTable 2). Tubificids w~re as sensitive to the material as the most sensitive fish.
Water fleas ~Daphnia magna), seed shrimp ~os~racod) and snails .` ~

i7~19 tPhysa ~p.) were approximately as sensitive to the toxi~ant a3 fl~h other than carp and white sucker. Dragonfly naiad3 ~Macromia 9p. ), back~winners (No~onecta sp~), snails (Pleuro-cera ~p.), and clams ~Corbicula sp. and ~phaerium 8p. ) were more resistant than mo~t of the fishes, and the LC 50 values for these invertebrate~ are approximately l0 times tho~a ~or ~ish.
EXAMPLE l0 Outdoor pool test3 were conducted using 50% formu-; 1~ lation of khe ~oxican~ N-(2-hydroxysthyl) digeranylamine as in~icated in E~ample 8. As shown in ~able 3, small carp ~ ~4-6 cm.) and rainbow trout were completely eliminated at ; all con~en~rations in 96 hour exposures. Some whi~a suckers an~ larger carp (l9 cm.) survived exposure~ to 0.l0 and 0.15 mg./liter, bu~ none survived conce~ntrations o O. 2 mg./liter ~ or higher. Speaie~ having comple1:e survival at all concen-; ~ra~ions include goldfish, grass carp (~tenopharyngodon idella), black bullhead (Ictaluru~3 melas), green su~fish, bluegill, largemouth bass (Micropterus salmoides), an~
walleye. Some ~athead, minnows, channel catfish, and yellow perch ~ied at ~.30 mg./liter of toxicant, but all survived lower concontrations. ~-EXAMPLEZ ll ~valuation of di(terpenyl) amino alkanol compounds where ~he ~erpenyl groups are linalyl, citronellyl, and the alkanol groups are 2-hydroxyethyl l,l-dimethyl-2-hydr~xy-ethyl, l-methyl-2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxy-i propyl, 4-hydrobutyl and 5-hydroxypentyl in tests e~uivalent to ~hose indicated in Examples 8 and l0 will produce substan-Z 30 ~ially the sama selective con~rol o~ carp specie~.

- . , . - . .:
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~V4~37V~3 To determine ~he influence of pH of the water used on the toxicity of the terpenylaminoalkanol~ evaluated, experiments were conducted with green sunfi3h (Lepomis cyanellus) u~ing oft water at 12C. and chemically bu~fered ovèr the range of pH 6 to pH 9. The results shown in Tabla 4 indicate that the salective toxicants are not deactivated by alkaline water, but rather increase significantly in activiky.
Thus, 1.85 mg./li~er is ~eeded for LC 50 control at p~ 6.0 but only 0.28 mg./liter is needed for the equi~alent control at pH 9Ø These re~ults show that it is difficult to state in advance the optimum level of toxicant needed to selective-ly control a ~ish specles and that the hardness of water the pH and the temperature all must be careully con3idered in arriviing at ~he optimum level of toxicant to be applied to a particular body of water.
~XA~L~ 13 The selective toxicant, N-(2-hydroxyethyl) digeranyl-amine was evaluated against bluegiLl in waters of hardness ~0 of 12, 44, 170 and 300 p.p.m., total hardness as CaCo3. The 96 hour LC SO's ~mg./li~er) for bluegill corresponding to the ~
sbove hardness were 0.84; 0.72, 0.48 and 0.33 respeatively. ~ -Generally the harder waters are also higher in pH.
~, . .
The above resulks dQmonstrate the unexpected im- ~ ;
provements of the in~tant terpenylaminoalkanol toxicants over the only two registered fish toxiaants, Rotenone and antimycin.
~oth Rotenone and antimycin are non-selective or carp and are adversely af~eated by p~. In contrast the specific amino-alkanols o~ this inventlon are selective to aarp and ef~ective ; 30 in waters o high pH. ~ ~
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Toxicity of N-(2-hydroxyethyl) Digeranylamine (50% Formulation) Exposed to Fish in 4,000 Liter Outdoor Plastic Pool % kill for 96 hour expo ~ e to b~dcant (mq/l) Species 0. ïo--- o . i3 o . 20 0 30 Rainbow trou~ 100 100 100 100 (5almo gairdneri) Goldish (Carassius auratus) Carp (small) 100 1`00 100 100 (Cyprinus carpio) Carp (large) 27 66 100 100 -(Cyprinus aarpio) Grass aarp 0 0 0 0 (c ~ idella) Fathead minnow 0 10 10 80 (Pimephalas p~ las) White sucker 20 70 100 100 (Catostomus commersonl) ~argemouth bufalo 0 20 20 100 (Ictibous cyprlnellu~) Black bullhead 0 0 0 ~Ictalurus melas) Channel catfish 0 0 0 40 (Ictalurus punctatus) Green sun~i~h 0 0 0 (~e~ cyanellu~~
~luegill 0 0 0 0 (Lepomis macrochirus) Largemouth bass 0 0 0 0 (Micropterus salmoides) :
_ .
Yellow perch 0 30 0 50 :
(Perca 1avescens) -Walleye 0 10 0 0 (Sti~ostedion vitreum) - ~"

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~(~3'~ ~3113 Toxicity of N-(2-hydroxyethyl) Digeranylamino (tech) to green - .

LC 50 and 95% confid n_e_interv (mg/liter) at S ~_ 3 hours ~~~-ours _ 24.hours 96 hoar~ .
6.0 6.34 5.00 2.~4 1.85 :~ :
5.57-7.21 4.36-5.73 2.30-3.52 1.57-2.19 7.5 2.47 1.64 1.00 0.~9 2.06-2.96 1.43-1.8B 0.893-1.12 0.739-~.930 8.0 ~ - 0.520 0.520 0~464-0.582 0.464-0.582 9.0 0.870 --~ 0.360 0.268 0.750-1.01 ~.298-0.435 0.210-0.341 ' ,~
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Claims (14)

The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:

1. A selective fish toxicant for controlling trash fish populations comprising an inert carrier and an effective amount of about 20-95 per cent by weight of a terpenylaminoalkanol or its acid salt, having the formula:

wherein T is a radical selected from the group consisting of geranyl, citronellyl, bupleuryl, neryl, lavandulyl, linalyl, myrcenyl, isobornyl and tetrahydrogeranyl;
R is independently hydrogen or C1-4; and x is an integer from 1 to 4.

2. A toxicant according to claim 1, wherein T is geranyl.

3. A toxicant according to claim 1, wherein the toxicant is a 50 per cent solution of N-(2-hydroxyethyl) digeranylamine hydrochloride in water.

4. A process for selectively controlling fish populations especially carp and white sucker species which comprises treating the water wherein said fish reside with an amount in the range of .03 to 10 parts per million parts of water of an aminoalkanol toxicant or water-soluble salt thereof, said toxicant having the formula:

wherein T is a radical selected from the group consisting of geranyl, citronellyl, bupleuryl, neryl, lavandulyl, linalyl, myrcenyl, isobornyl and tetrahydrogeranyl;
R is independently hydrogen or an alkyl radical containing one to four carbon atoms; and x is an integer of 1 to 4.

5. A process according to claim 4, wherein said toxicant is applied at an effective rate of from about 0.03 to 1.5 parts active toxicant per million parts of water treated.

6. A process according to claims 4 or 5, wherein said water-soluble salt is selected from the group consisting of inorganic acid salts, organic acid salts, and quaternary ammonium salts of said amino-alkanol toxicant.

7. A process according to claims 4 or 5, wherein the toxi-cant is applied to the water as a hydrochloride salt.

8. A process according to claim 4, wherein a 50% aqueous solution N-(2-hydroxyethyl) digeranylamine hydrochloride is applied at an effective rate of from 0.05 to 0.13 parts active toxicant per million parts of water treated.

9. A process according to claims 4 or 5, wherein T is 3,7-dimethyloctyl.

10. A process according to claims 4 or 5, wherein the toxi-cant is N-(2-hydroxyethyl) di(3,7-dimethyloctyl) amine.

11. A process according to claims 4 or 5, wherein T is isobornyl.

12. A process according to claims 4 or 5, wherein the toxi-cant is the hydrochloride of N-(2-hydroxyethyl) diisobornylamine.

13. A process according to claim 4, wherein the controlled species is carp.

14. A process according to claim 4, wherein the controlled species is white sucker.