DE2029707A1 - Anti-virus preparations and their uses - Google Patents

Description

PATENT LAWYERS MUNICH 2
VAL 33
TEL. 0311/226394
295051
CABLES: THOPATENT
TELEX: TO FOLLOW Dipi.-chem Dr.D.Thomsen mpung. H. Tiedtke
Dipi-chem. G.Bühlmg 2029707 FRAN KFU RT (MAl N) 50
FUCHSHOHL 71
TEL. 0611/514666 Dipi-mg. W.Weinkauff

Reply requested to: Please reply to:

8000 Munich 2 June 16, 1970 case PP 21980 / T 3664

Imperial Chemical Industries Limited London / Great Britain

Anti-virus preparations and their uses

The invention relates to anti-virus preparations and to methods of combating plant viruses.

The anti-virus preparation of the invention contains as an active ingredient a compound of the general formula '

Nir

H-C-HR * - Q

or a salt thereof in which R ¹ , R ² , R ³ and R ^{4 are} hydrogen atoms or unsubstituted or substituted hydrocarbyl groups (hydrocarbyl groups) or amino groups

represent and also R ¹ and R ² together with one of them

00 9 852/2111

adjacent nitrogen atom represent a heterocyclic group and Q is either (a) an amino group of the formula SR R, in which R and R are as defined above for R and R, or (b) an imino group of

7 8 7 8

Forme.l N = CR R represents, in which R and R are hydrogen atoms or represent unsubstituted or substituted hydrocarbon groups or heterocyclic groups.

Preferred compounds for use as active ingredients The anti-virus preparations are those in which hydrocarbon groups Alky! groups or Ary! groups are »

According to a preferred embodiment, the invention therefore includes eh anti-virus preparation which _s as active ingredient a compound of general formula

R ¹ NR ³

.N-C- NIT -

R ² '

12 3 4 or a salt thereof, wherein R,. R, R and R are hydrogen atoms or 'not-substituted © © the substituted one Represent alkyl groups or aryl groups or amino groups

ι 2
and in addition R and R together with a nitrogen atom adjacent to them represent a heterocyclic group and Q is either (a) an amino group of the formula NR R, "in which R and R ^{w represent} hydrogen atoms or unsubstituted or substituted alkyl groups or aryl groups.

009852/21 1 1

7 8 or (b) is an imino group of the formula N = CR R, in which

R ⁷ and R ^{8 represent} hydrogen atoms or unsubstituted or substituted alkyl or aryl groups or heterocyclic groups.

According to a more preferred embodiment of the invention the anti-virus preparation of the invention contains as active ingredient a compound of the general formula

R ¹ NR ³

N-C- NR * - Q.

12 3 4 or a salt thereof, in which R, R, R and R are hydrogen

1 represent 2 atoms and also R and R amino groups, lower Alkyl groups with 1 to 6 carbon atoms, phenyl groups, optionally substituted with one or more halogen atoms, or alkyl, alkoxy, alkylthio or alkanesulfonyl

represent groups, or R and R together with the adjacent nitrogen atom represent a 5- or 6-membered heterocyclic ring which may contain other heteroatoms, and in which Q is either (a) an amino group NR R, in which R ⁵ and R represent hydrogen atoms or (b)

7 8 7

is an imino group of the formula N = CR R, in which R and

R hydrogen atoms, alkyl groups with 1 to 12 carbon atoms, pyridyl groups, phenyl groups, optionally with substituted for one or more halogen atoms, or represent nitro groups.

009852/2111

According to a particularly preferred embodiment According to the invention, the anti-virus preparation contains as active ingredient a compound having either (a) of the formula:

R ¹ NH

N - Ο'- NH - NKL

1 2 or a salt thereof, in which R and R are hydrogen atoms, Represent alkyl groups having 1 to 6 carbon atoms, amino groups, a 4-alkanesulfonylphenyl group or in which R

and R together with the adjacent nitrogen atom represent a 4-morpholino group; or (b) the formula:

R ¹ NH R ⁷

^^ N -C- NH -N = C 2 ^

R '

12th
wherein R and R are hydrogen atoms, lower alkyl groups with 1 to 6 carbon atoms, 4-halophenyl, 4-alkylphenyl, 4-alkoxyphenyl, 4-alkylthiophenyl or 4-alkanesulfon'yl-

"7 Q

represent phenyl groups, and R and R represent hydrogen atoms, Alkyl groups with 1 to 12 carbon atoms, 4-pyridyl groups, phenyl groups, 2,4-dichlorophenyl, 4-chlorophenyl or Represent 4-nitropheny groups.

The compounds can be used as such, i.e., as free bases, in the preparations of the invention, however, when the free bases are unstable, the compounds of the invention are conveniently in the form of their salts

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used. Such salts can be halides, sulfates. Phosphates, Carbonates, bicarbonates, nitrates, acetates, p-toluenesulfonates, p-nitrobenzoates and oxalates, among others. Hydrochlorides are particularly suitable, as are the hydroiodides,

Special compounds used as active ingredients in the Anti-vifus preparations useful are those set out in Table I below, which of the general formula;

R ¹ NR ³

"4
NC NO. Q

correspond.

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Table I.

Connection no

R ¹

E ²

R ³

NH ₂

NK ₂

CH ₃

MB ₂

- (CHJ ₉ -O- (CHj-

g) ₂

(CHj) ₂ CHCHg

HS ₂

^CH 3 ^S0 2

vs.

CK

CH

CH ₂ - /

N = C (CH,) g

CH

S0 ₂ /

10

CH

S ^

00985272111

Table I (continued)

Connection no.

11

12th

CH ₃ O

CH.

CH.

CH,

CH,

CH _n

CH ₃

N = CH (CK ₂ ) _{Λ 0} CH ₃

17th

CH,

CH, ^:

18th

OB _x -

Two particularly valuable special compounds are:

NH

- ΝΗ · ΝΗ.

CH ₃ NH

^ "N -C- NH'NH.

No. 2 of Table I No. 6 of Table I

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The inventive compounds that are useful as active ingredient in the anti-virus preparations of the invention can, for example, by reacting an S-methylisothiosemicarbazide salt, for example the hydroiodide, with an amine and more generally by reacting a hydrazine with a suitable, - substituted isothiouronium salt, for example the Halide, including those compounds in which R ₁ and R 3 together with the adjacent nitrogen atom form a ring, can be obtained.

The anti-virus preparations and compounds of the invention have been found to be active against intrapeutic Are infections caused by several major plant viruses, including the following:

Cucumber Mcsaikvirus (Cucumis Virus 1, Smith) Tobacco Mosaic Virus (Nicotiana Virus 1, Smith) Potato Virus Y (Solamim Virus 2, Smith)

A particularly valuable characteristic of the activity of some of the compounds of the present invention is their ability to act as intrapeutic antiviral agents, that is, their ability to migrate in the plant to combat infection thereupon which removes a site of original application of a compound is. Thus, a compound of the invention or a preparation containing them

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applied to the soil surrounding the roots of a plant and then taken up by the plant through its roots to fight the viruses in the plant.

The anti-virus aminoguanidine derivatives of the invention are used in the control of plant pests in a variety of ways Way used. They can be found on the foliage of an infected plant, on the seeds or on the ground, in which the plants germinate or are to be planted.

According to a further embodiment, comprises Invention therefore a method for combating undesirable viral infections in plants, which consists in that an aminoguanidine derivative on the location of the plant, as defined above, or a preparation of the type defined above is applied.

According to a further embodiment of the invention, this comprises a method for combating viruses in plants, which consists in applying an anti-virus aminoguanidine derivative or a preparation of the type defined above to the location of the plant.

009852/211 1

According to a further embodiment of the invention this includes a method of combating viruses in agricultural soil, which consists in / that one on the Soil an aminoguanidine derivative or a preparation of the type defined above applies.

The aminoguanidine derivatives of the invention are preferred used in the form of compositions or preparations. The type of preparation used in each case depends on the specific purpose for which it is to be used.

The preparations can be in the form of dusty powders or granules in which the active ingredient is present mixed with a solid diluent or carrier. Suitable solid diluents or carriers can, for example Kaolin, bentonite, kieselguhr, dolomite, calcium carbonate, talc, powdered magnesium oxide, fuller's earth, Plaster of paris, Hewitt's earth, diatomaceous earth, and china clay (China-Clay). Preparations for the finishing of seeds contain, for example, an agent that reduces the adhesion of the Preparation supported on the seed, for example a mineral oil.

The preparations can also be in the form of dispersible powders or granules, which in addition to the active ingredient a wetting agent to facilitate dispersion of the

009852/21 11

Powder or grains contained in liquids. Such Powders or granules can contain fillers, suspending agents, and the like.

The preparations can also be in the form of liquid preparations are present, which are to be used as immersion baths or sprays, and generally aqueous dispersions or are emulsions which contain the active ingredient in the presence of one or more wetting agents, dispersants, emulsifiers or contain suspending agents.

Wetting agents, dispersants and emulsifiers can be cationic, anionic or nonionic Be type. Suitable agents of the cationic type are, for example quaternary ammonium compounds, for example cetyltrimethylammonium bromide. Suitable agents of the anionic type are, for example, soaps, salts of aliphatic Monoesters of sulfuric acid, for example sodium lauryl sulfate, Salts of sulfonated aromatic compounds, for example sodium dodecylbenzenesulfonate, sodium,. ' Calcium or ammonium lignosulfonate, butyl naphthalene sulfonate and a mixture of the sodium salts of diisopropyl and triisopropyl naphthalene sulfonic acid. Suitable agents of the non-ionic type are, for example, the condensation products of ethylene oxide with fatty alcohols, such as oleyl alcohol or cetyl alcohol, or with alkylphenols such as octylphenol, nonylphenol

009852/2111

and octyl cresol. Other non-ionic agents are the partial esters, those of long chain fatty acids and hexitol anhydrides are derived, the condensation products of the partial esters with ethylene oxide and the lecithins.

Suitable suspending agents are, for example, hydrophilic Colloids / for example polyvinylpyrrolidone and sodium carboxymethyl cellulose as well as the vegetable gums, for example acacia and gum tragacanth.

The aqueous dispersions or emulsions can by dissolving the active ingredient or the active ingredients in one organic solvent, which can contain one or more wetting agents, dispersants or emulsifiers, and subsequent Addition of the mixture thus obtained to water, which also has one or more wetting, dispersing or Emulsifying agents can be prepared. Suitable organic solvents are ethylene dichloride, isopropyl alcohol, Propylene glycol, diacetone alcohol, toluene, kerosene, methylnaphthalene, xylenes and trichlorethylene.

The preparations to be used as sprays can also be in the form of aerosols, in which the approach in a container is kept under pressure in the presence of a propellant such as fluorotrichlorine than or dichlorodifluoromethane.

009852/2111

By incorporating suitable additives, for example to improve the distribution, the adhesive force and the resistance to rain on treated surfaces, the various preparations can be better adapted to the various uses for which they are intended will.

The preparations which are to be used in the form of aqueous dispersions or emulsions are generally supplied in the form of a concentrate which contains a high proportion of the active ingredient or ingredients, the concentrate being diluted with water before use. These concentrates are often required to be able to withstand storage for prolonged periods and, after such storage, to be able to be diluted with water in order to form aqueous preparations which remain homogeneous for a sufficient time to enable their application by a conventional spray device. The concentrates can expediently contain 10 to 85% by weight of the active ingredient or active ingredients and generally 25 to 60% by weight of the active ingredient or active ingredients. When diluted to form aqueous preparations, such preparations can contain varying amounts of the active ingredient or active ingredients, depending on the purpose for which they are to be used, but an aqueous preparation containing between 0.001 and 1.0% by weight of the

00 9852/2111

Active ingredient or containing active ingredients, can be used.

Of course, the biologically active preparations of the invention can be used in addition to an aminoguanidine derivative contain one or more other compounds with biological activity. You can also use one or more stabilizers contain.

The invention is illustrated by the following examples, in which all percentages of the amounts of Be components are weight information and relate to weight of the complete preparations.

example 1

This example illustrates the preparation of 1,1-dimethyl-3-aminoguanidine hydroiodide with the structural formula :

CH ₃ NH

^ N - C - NH-NH- -HJ

(a) 20.0 g of S-methylisothiosemicarbazide hydroiodide were dissolved in 80 ml of a 25 to 30% strength solution of dimethylamine in water , and the reaction mixture was left to stand at room temperature overnight. Bs then went dry

009852/2111

- 15 - ::: ■■■ .. ■■:; :

evaporated, and the residue was recrystallized from ethanol, 10.5 g of l, l-dimethyl-3-aminoguanidine (Melting point 184 ° to 185 ° C).

(b) A mixture of 12.3 g of N, N, S-trimethylisothiouronium iodide, 2.6 g of hydrazine hydrate and 60 ml of ethanol was added for 4 hours held at reflux for a long time. After cooling, 8.0 g 1,1-Dimethyl-3-aminoguanidine (melting point 178 to 180 C) obtained and after partial evaporation a further yield of 1.4 g. The recrystallization from ethanol resulted a material with a melting point of 184 to 186 C.

Example 2

This example illustrates the preparation of a series of salts of 3-amino-l, l-dimethylguanidine.

A solution of 3-amino-l, l-dimethylguanidine as Carbonate and / or bicarbonate for use in the manufacture of other salts were made in the following manner.

A solution of 70 g of barium hydroxide octahydrate in 500 ml of hot water became a solution of 30.8 g of 3-amino-1,1-dimethylguanidine sulfate given in 100 ml of water. After adding excess solid carbon dioxide was allowed the mixture to cool to room temperature and then

009852/21 1 1

filtered through "CeIite". The solids became thorough washed with water, and the combined filtrates diluted with water, one liter of a solution with a Content. Of about 0.2 mol of 3-amino-l, l-dimethylguanidine as Carbonate or bicarbonate resulted.

The solution prepared above (100 ml) was added in an equimolar amount (i.e., 0.02 mol) of the corresponding Acid (in the case of a volatile acid, a 20% molar excess was used) dissolved or suspended in water, until the development of carbon dioxide ceased. The solution was then evaporated to dryness, the in the products listed in the table below.

analysis

Anion of S
Salt melting solution with
dot tel to
o _c recrystalline
lization Isopropanol found H N calculated K 20.4 p-toluenesul-
fonat 168 Isopropanol C. 6.4 - *, ■ C. bromide 214
219 Isopropanol 5r9 3QA «*. 6.0 2610 p-nitro
benzoate Ethanol 19.5 6.0 2 ^ 6 19.8 ₅ / Oxalate di-
hydrate 192
195 Ethanol /
Methanol 7.4 4 ^ 6 7 ^ 9 27 ^ 9 Dihydrogen
phosphate 191 Ibopropanol 28.3 6.8 28.0 29 ^ 1 6.5 40 * 4 chloride 209
21 * 2 Ι7ι6 7, 9 -
40.4 8.0 26.6 26.0

009852/21 1 1

The following salts were also produced: Das

Benzoate as a low-melting semi-solid, the sali-

27 cylat as pale orange gum n ^ 1.5622 as well as the dichloro

27 acetate as pale yellow gum n ^ 1.5308.

In the following examples the names: "LUBROL", "AROMASOL", "DISPERSOL ¹¹ ," LISSAPOL "," CELLOFAS "are trademarks.

Example 3

An emulsion concentrate was prepared by adding the ingredients listed below to the ones indicated Portions mixed together and the mixture stirred until all ingredients were dissolved.

Compound No. 9 from Table I 10%

Ethylene dichloride 40%

Calcium dodecylbenzenesulfonate 5%

"Lubrol" L. 10%

"Aromasol" H 35%

Example 4

It became a preparation in the form of grains, which " are readily dispersible in a liquid, e.g., water, prepared by the first three of the following

009852/2 1 1 1

Listed ingredients were ground together in the presence of added water and then in the sodium acetate were mixed. The resulting mixture was dried and passed through a British Standard mesh screen, Dimension to 100, allowed to pass in order to obtain the desired grain size.

Compound no. 14 from Table I 50%

"Dispersol" T ... 25%

"Lubrol" APN 5 1.5%

Sodium acetate 23.5%

Example 5

The ingredients listed below were all ground to one another in the proportions indicated to produce a powder formulation that is easily dispersible in liquids.

Compound no. 16 from Table I 45% "Dispersol" T 5%

"Lissapol" NX 0.5%

"Cellofas" B 600 2%

Example 6

Compound No. 2 from Table I was used as the active ingredient 009852/2111

dissolved in a solvent, and the resulting liquid was sprayed on grass from fuller's earth. The solvent was then allowed to evaporate to a granular Manufacture preparation ..

Compound of example 1. . 5%

Granules from fuller's earth or china clay (china clay) 95%

Example 7

A preparation suitable for use as a seed finish was made by mixing all three of the following listed ingredients in the specified proportions.

Compound No. 12 from Table I 50% mineral oil 2%

China clay 48%

Example 8

A dusty powder was made by mixing the active ingredient listed below with talc in the anos ^ even Shares made.

0 0 9 8 5 2/2111

Compound no. 6 from Table I 5% '

Talc 95%

Example 9

A mix was made by mixing the following listed ingredients using a ball mill and subsequent formation of an aqueous suspension of the ground Mixture made with water.

Compound No. 7 from Table I 40%

"Dispersol". 10%

"Lubrol" 1%

Water 49%

Example 10

Approaches similar to those outlined in the previous examples were followed, but the as active ingredient a compound of Examples No. 1 or contained, by appropriate methods such as those described in each specific example.

"LUBROL" L is a condensate made from nonylphenol with

Ethylene oxide.

"AROMASOL" H is a solvent mixture of Al-

kylbcnzolcn.

009852/21 1 1

"DISPERSOL" T is a mixture of sodium sulfate ■ and a condensate of formaldehyde

with the sodium salt of naphthalenesulfonic acid.

"LUBROL" APN 5 is a condensate of nonylphenol with

Ethylene oxide.

"CELLOFAS" B 600 is a sodium carboxymethylcellu-

loose-thickeners.

"LISSAPOL" NX is a condensate of nonylphenol with

A "ethylene oxide.

"GOULAC" is a calcium lignosulfonate.

The preparations according to the invention were prepared and tested against various viruses in the following way, and the results of these tests are shown in the table below. In the tests, the active chemical compounds, those listed in Table I above, by grinding the compounds with a ball mill with Dispersol T and by adding Set water.

Cucumber, tomato, tobacco and beet seedling plants grown in 38.1 mm (1 1/2 inch) diameter pots containing John Innes No. 1 compost were treated with the compound which is like was set up above, sprayed to a maximum liquid retention, and a root soak in a ratio of 10 ml per pot (plant) was used. There were three repetitions per treatment each

009852/21 11

Viral disease made .. After a period of 2 days, the cucumber, tomato and tobacco seedlings were mechanically processed to allow the chemical to be absorbed Rubbing an infectious juice on the cotyledons, and the beet seedlings were infected by virus-carrying aphids could feed on the leaves.

Fourteen days later, i.e., sixteen days after spraying, the seedlings were visually inspected for disease. The results, which are given in Table II below, are expressed as a graduation of 0, 1, 2 or 3, with the grading of 0 being severe Symptoms of a viral disease and grade 3 indicates that no symptoms of the viral disease could be detected.

Table II

Tobacco mosaic cucumber mosaic potato · · Sugar beet virus on To- virus on Gur- virus Y äjf yellow virus mate plants, kenpflanze Tobacco Pfian- on sugar- (variety: (Variety: zen (VacLe beet plant

Ailsa Craig) Butcher's Krark- tat .: White zen

Infected mental registry Burley)

similar plants ο 11 O

not infected
Reference plants 3 3 3 3

Connection No. 1
(Table I) 1 3 3 . 3

Connection No. 2 (Table I) 3 33 3

Compound No. 3 (Table I) O 3 3 - A ₁

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Table II (continued)

Tobacco mosaic Cucumber mosaic virus on potato · beet To- virus to virus Gur Y on Golbvirus rtiatenpf lances kenpflanzen Tsbakpfjsn- on sugar (V _a rietät: (variety: zen (Vsrie- rübenpfüan-Ailsa Craig) · Butcher s Ksrk- tat: White zen heitsregister Bur ley)

Connection No. 4 ■

(Table I) O 3 3 3

Compound No. 5
(Table I) "O 2 3 2

Connection No. 6 ■

(Table 1) 2 3 3

Compound No. 7
(Table I) O 1 2 2

Compound No. 8
(Table I) O 1 3 1

Compound No. 9

(Table I) O 1 3 2

Compound # 10
(Table I) 0 1 3 2

Compound # 11
(Table I) 0 1 2 3

Compound # 12
(Table I) O 2 2 1

Compound # 13
(Table I) O 1 3 3

Compound # 14

(Table I) 0 l 2 1

Compound # 15
(Table I) 0 1 12

Compound # 16
(Table I) 1 3 Ii

Compound # 17
(Table I) 1 3 2 O -

Compound # 18

(Table I, ₀ % 9 8 5 2/2 1 1 f

Claims (12)

Claims 1. Anti-virus preparation, characterized by a Active ingredient content of a compound of the general formula; t »l _NR 3 NC- NR ⁴ -Q- 12 3 4 or a salt thereof, wherein R, R, R and R are hydrogen atoms or unsubstituted or substituted hydrocarbon represent groups or amino groups and 1 2 the R and R together with an adjacent nitrogen atom eiie represent heterocyclic group and Q is either (a) an amino group of the formula NR R, in which 5 6 1 'ο R and R have the meaning given above for R and R ″ 7 8, or (b) an imino group of the formula N = CR R be 7 8 indicates where R and R are hydrogen atoms or unsubstituted or represent substituted hydrocarbon groups or heterocyclic groups. 2. Anti-virus preparation according to claim 1, characterized by an active ingredient content of the given general formula or its salt, in which R ¹ , R ² , R ³ and R ^{4 represent} hydrogen atoms or unsubstituted or substituted alkyl groups or aryl groups or amino groups and 1 2 the R and R 'together with a nitrogen atom adjacent to them represent a heterocyclic group, and Q either 009852/2111 (a) is an amino group of the formula NR R wherein R and R is hydrogen or unsubstituted or substituted Represent alkyl groups or aryl groups or (b) denotes an imino group of the formula N = CR R ⁸ , in which R ⁷ and R represent hydrogen atoms or unsubstituted or substituted alkyl or aryl groups or heterocyclic groups. 3. Anti-virus preparation according to one of the preceding claims, characterized by an active ingredient content a compound of the general formula or its salt, in which R, R, R and R are hydrogen atoms and also R. and R amino groups, lower alkyl groups having 1 to 6 carbon atoms, Phenyl groups, optionally substituted by one or more halogen atoms, or alkyl, alkoxy, 12th Alkylthio or alkanesulfonyl groups or R and R together with the adjacent nitrogen atom a 5- or 6-membered heterocyclic ring containing other heteroatoms can represent, and Q is either (a) an amino group of the formula NR R, in which R and R represent hydrogen atoms 7 8, or (b) an imino group of the formula N = CR R 7 8
tet, in which R and R represent hydrogen atoms, alkyl groups having 1 to 12 carbon atoms, pyridyl groups or phenyl groups, optionally substituted by one or more halogen atoms, or nitro groups. 009852/2111 4. Anti-virus preparation according to one of the preceding Claims, characterized by an active ingredient content of a compound with either (a) the mold N - C • NH - NH or a salt thereof, wherein R and R are hydrogen atoms, alkyl groups having 1 to 6 carbon atoms, amino groups, _t is a 4-Alkänsulfonylpheny! represent group or wherein R and R ² represent together with the adjacent nitrogen atom form a 4-morpholino group? or (b) the formula: R ¹ NH NH - N = ( R ⁷ Z ^ R ⁸ Il C - 1 2
wherein R and R are hydrogen atoms, lower alkyl groups with 1 to 6 carbon atoms, 4-halophenyl, 4-alky! phenyl, 4-alkoxyphenyl, 4-alkylthiophenyl or 4-alkanesulfonyl 7 8 pheny! groups and R and R represent hydrogen atoms, Alkyl groups with 1 to 12 carbon atoms, 4-pyridyl groups, Phenyl groups, 2,4-dichlorophenyl, 4-chlorophenyl or Show 4-Nitropheny! Groups " 5. Anti-virus preparation according to one of the preceding Claims, characterized by an active ingredient content of at least one of the compounds from Table I, either not in the form of a salsa or in the form of an acid 003852 / 2.111 addition salt. 6. Anti-virus preparation according to one of the preceding Claims, characterized in that the active ingredient is a compound of the formula CH ₃ NH ^ N - C - NHNH ₂
CH ₃ or contains a salt thereof. 7. Anti-virus preparation according to one of the preceding claims, characterized in that it is used as an active ingredient a compound of the formula CH ₃ NH - C - NHNH ₂ II or contains a salt thereof. 8. anti-virus preparation according to any one of the preceding claims, characterized in that it is the active ingredient compound in the form of an acid addition salt, wherein the acid is hydrohalic acid. 9. Use of the preparation according to one of the preceding claims for combating unwanted viral infections on plants by applying an aminogua- 00 9852/2111 nidine derivative or one containing an aminoguanidine derivative Preparation according to one of the preceding claims on the location of the plant. 10. Use of the preparations according to one of the preceding claims for combating viruses on plants by applying an anti-Yirus aminoguanidine derivative or a preparation containing an aminoguanidine derivative according to one of the preceding claims the location of the plant. 11. Use of the preparations according to one of the preceding claims for the control of viruses on agricultural soil by applying a Aminoguani dinderivates ⁰ or an aminoguanidine derivative-containing preparation according to any preceding claim on the floor · 009852/2111