NL7810350A - PREPARATION WITH GROWTH REGULATORY EFFECT AND USE OF THIS PREPARATION IN AGRICULTURE AND GARDEN CONSTRUCTION. - Google Patents

Description

f ·; «* £ -.- · ..: - 'ί

Si-PHN 9262_ '___.

N.V. Philips' Incandescent lamp factories

Preparation with growth regulating effect and use of this preparation in agriculture and horticulture

The invention relates to a composition with a growth regulating effect, as well as to a method for preparing this composition. The invention further relates to the use of this preparation in agriculture and horticulture.

In agriculture and horticulture it is often desirable to regulate the growth of trees, shrubs or non-woody plants or parts thereof. For example, it may be necessary to inhibit the growth of the above plants such as fruit trees, hedge shrubs or lawn-10 'grass. It can also be advantageous to influence the growth of plant parts. For example, by hindering the growth of the buds of sugar cane, the cane stems can develop better and the sugar yield is increased.

It may also be important to inhibit or suppress the development of side shoots, especially in those plants where frequent side shoots occur, such as various ornamental plants, tomato plants and tobacco plants. These side shoots use a lot of nutrients, which therefore cannot benefit other plant parts, such as leaves, flowers and fruits. In tobacco, the need for side shoot inhibition is strongly present, because the size and quality of the tobacco plants is very adversely affected by the development of side shoots, and especially in large plots with: abak removing by hand the side shoots are time consuming 25 and therefore expensive.

It has now been found that compounds of the general formula R3 y-y / N ~ CE2 \ R1 ^) -> = - <^ ^> vn - N - ch "^

I I

R4 R5 78 1 0 3 5 0 4 * -2-t PHN 9262__________ wherein R} is an optionally halogen-substituted alkyl, alkenyl, alkoxy, alkenyloxy, alkylthio, alkenylthio, alkoxyalkyl or alkylthioalkyl group of 3 to 12 carbon atoms, a mono-, bi- or tricyclo-5 alkyl group of 3 to 12 carbon atoms, a phenyl, phenoxy, phenylthio, phenylalkyl, phenylalkoxy or phenylalthio group with 6 to 10 carbon atoms, which phenyl group or whose phenyl group is optionally substituted with halogen or with alkyl, alkoxy or alkylthio, which alkyl, alkoxy or alkylthio groups have 1 to 6 carbon atoms and may optionally be halogenated, or a furylalkyl or tbienylalkyl group with 5 to 8 carbon atoms, R 2 is a hydrogen or halogen atom, or wherein R 1 and R 2 together represent a trimethylene or tetramethyl group,

Rg and Rg are the same or different and represent a hydrogen atom or an alkyl or alkanoy group of 1 to 4 carbon atoms, Rg is a hydrogen atom or an alkyl group of 1 to 4 carbon atoms, and n is 0 or 1, as well as salts and complexes of these compounds, have a growth regulating effect.

It has been found that particularly active are preparations which contain as active substance a compound of the general formula

--- NH - CH

e; - NH-CH 2 wherein R 1 represents an n-alkyl group of 5 to 9 carbon atoms or a phenylethyl group, or salts or complexes thereof.

78 1 0 3 5 0 i -3-

"1" T

PHN 9262

Examples of highly active compounds are: I

(1) 2- (4-n-pentylphenyl) imino-hexahydropyrimidine, (2) 2- (4-n-hexylphenyl) imino-hexahydropyrimidine, (3) 2- (4-n-heptylphenyl) imino-hexahydropyrimidine 5 (4 ) 2- (4-n-octylphenyl) imino-hexahydropyrimidine, (5) 2- (4-n-nonylphenyl) imino-hexahydropyrimidine and (6) 2 - 4- (2-phenylethyl) phenylimino-hexahydropyrimidine.

Other compounds which are also suitable for use in compositions according to the invention are: (7) 2- (4-n-hexyl-phenyl) imino-hexahyropyrimidine, (8) 2- ( 4-n-octyloxyphenyl) imino-hexahydropyrimidine, (9) 1-methyl-2- (4-n-hexylphenyl) imino-hexahydropyrimidine, (10) 2- (4-n-hexylthiomethylphenyl) imino-hexahydropyrimidine, 15 (11) 2- [4- ^ 2- (4-methylphenyl) ethyl} phenyljimino-hexahydropyrimidine, (12) 2- (4-sec-butylthiomethylphenyl) imino-hexahydropyrimidine, (13) 2- (4-dsopentylthiophenyl) imino-hexahydropyrimidine, (14) 1-methyl-1-2 "[4- (1-methylheptylthio) phenyl-jimino-hexahydro-pyrimidine, (1-5) 2- [4- (1-methyl-butyl) phenyl] imino-hexahydropyrimidine, (16) 2- £ 4- (1-methylbutylthio) phenyl] imino-hexahydropyrimidine, (17) 2- (4-n-hexyloxyphenyl) imino-hexahydropyrimidine, (18) 2- [4- (1-methylheptylthio) phenyljimino-hexahydropyrimidine, 25 (19) 2- (4-n-octylphenyl) imino-4-methyl-hexahydropyrimidine, (20) 2- £ 4- (4-chlorobenzyloxy) phenyl imino-hexahydropyrimidine (21) 2- (4-n-octylfe) nyl) imino-hexahydropyrimidine acetate, (22) 2- (4-cyclohexylphenyl) imino-hexahydropyrimidine, (23) 2- (4-benzylphenyl) imino-hexahydropyrimidine, 30 (24) 2- [4- (2-chlo orallylthio) phenyljimino-hexahydropyrimidine, (25) 2- (3-chloro-4-n-propylthiophenyl) .imino-hexahydropyrimidine, (26) 2- (4-n-octylthiophenyl) imino-hexahydropyrimidine, (27) 2- (4 -n-decylthiopheny1) imino-hexahydropyrimidine, 78 1 0 3 5 0 -4- ΡΗΝ 9262_ (28) 2 - [_ 4- (4-methylphenylthio) phenyl] imino-hexahydropyrimidine, (29) 2- [4- (4- chlorophenyl thi o) phenyl] imino-hexahydropyrimidine, (30) 2- (4-n-dodecyloxyphenyl) imino-hexahydropyrimidine, (31) 2- (4-phenoxyphenyl) imino-hexahydropyrimidine, 5 (32) 2- [4- (4-methylphenoxy) phenyl] imino-hexahydropyrimidine, (33) 2- [4- (4-chlorophenoxy) phenyl imino-hexahydropyrimidine, (34) 2- (3-chloro-4-phenoxyphenyl) imino-hexahydropyrimidine, (35) 1,3-diethyl-2- (4-n-butypheny1) imino-hexahydropyrimidine, (36) 1,3-diacetyl-2- (4-cyclohexylphenyl) imino-hexahydropyrimidine, (37) 2- (4- n-heptylphenyl) iminoimidazoli dine, (38) 2- (4-n-hexylphenyl) imino-imidazolidine, (39) 2- (4-n-octylphenyl) imino-imidazolidine, (40) 2 - {[4- (2-chloroally lthio) f enyl] imino-imidazolidine, 15 (41) 2- [4- (1-methylheptylthio) phenyl] imino-imidazolidine, I (42) 2- [4- (2-methylphenoxy) phenyl] imino-hexahydropyrimidine, (43) 2 - [4- (3,5-dimethyphenoxy) phenyl] imino-hexahydropyrimidine, (44) * 2- (4-cyclohexylphenyl) imino-hexahydropyrimidine cinnamate, (45) 2- (4-n-propylphenyl) imino-hexahydropyrimidine, 20 (46) 2- (4-cyclohexylphenyl) imino-hexahydropyrimidine p-dodecylbenzenesulfonate, (47) 2- (4-n-octylphenyl) imino-hexahydropyrimidine p-dodecylbenzenesulfonate, (48) 2- (4 -n-butylphenyl) imino-hexahydropyrimidine p-dodecyl-25-benzene sulfonate, (49) 2- (4-cyclohexylphenyl) imino-hexahydropyrimidine acetate, (50) 2- (4-n-octylpheny1) imino-hexahydropyrimidine zinc chloride complex , (51) 2- (4-cyclohexylphenyl) imino-hexahydropyrimidine zinc acetate complex, (52) 2- (4-cyclohexylphenyl) imino-hexahydropyrimidine cuprite acetate complex, (53) 2- (4-cy clohexylphenyl) imino-hexahydropyrimidine phosphorous acid ethyl ester, 35 (54) 2- (4-cyclohexylphenyl) imino-hexahydropyrimidine phosphorous --- n-butyl ether, - 78 1 0 3 5 0

C

-5- PHN 9262 (55) 2- (4-tert-butylphenyl) imino-hexahydropyrimidine, (56) 2- [4- (2,5-dimethylphenoxy) phenyl] imino-hexahydropyrimidine, j (57) 2- (4 cyclohexylphenyl) imino-hexahydropyrimidine benzo- thiazole thiolate,! 5] (58) 2- (4-adamantylphenyl) imino-hexahydropyrimidine, I (59) 2- (3,4-tetramethylenphenyl) imino-hexahydropyrimidine, (60) 2- [4- | "2- (2-methylphenyi) ethyl] phenyl] imino-hexahydropyrimidine, (61) 2- [4- (2-furylethyl) phenyl] imino-hexahydropyrimidine, 10 (62) 2- [4- {2- (4-isopropoxyphenyl) ethyl] phenyljimino-hexahydro-pyrimidine, (63) 2- [4 "^ 2- (4-chlorophenyl) ethylphenyl-jimino-hexahydropyrimine, (64) 2- [4- ^ 2- (4-isopropylphenyl) ethylphenyl] imino-hexahydropy-1-rimidin, I (65) 2- [4-J 2- (4-ethoxyfettyl) ethyl] phenyl] imino-hexahydropyri-methyl, (66) 2- [{2- (2-n-butoxyphenyl) ethyl] phenyl] imino-hexahydropyrimidine , 20 (67) 2- (4-isopropylphenyl) imino-hexahydropyrimidine, and (68) 2- (4-n-butylphenyl) imino-hexahydropyrimidine.

Most of the aforementioned compounds are described in the non-prepublished Dutch patent application 7711390 in the name of the applicant; fungicidal activity is reported for these compounds.

Some of the above connections are new. New compounds that can be used in the compositions of the invention are: 2- [4- (2-chloroallylthio) phenyljimino-hexahydropyrimidine, m.p. 10 40 C; 2- (3-chloro-4-n-propylthiophenyl) imino-hexahydropyrimidine, mp 1 23 ° C; 2- (4-phenoxyphenyl) imino-hexahydropyrimidine, mp. 181 ° C; 2- [4- (4-methylphenoxy) phenyl-jimino-hexahydropyrimidine, 33 mp. 129 ° C 781 03 50 1 -6- PHN 9262__-2- [4- (4-chlorophenoxy) phenyl] imino-hexahydropyrimidine, m.p. 1530C; 2- (3-chloro-4-phenoxyphenyl) imino-hexahydropyrimidine, oil; 1,3-thy 1-2- (4-n-butyphenyl) imino-hexahydropyrimine, oil; 2- [4- (2-chloro-orallylthio) phenyl] imino-imidazolidine, m.p. 90 ° (j; 2- [4- (1-methylheptylthio) phenyl] imino-imidazolidine, oil; 2- [4- (2-methylphenoxy) phenyl] imino-hexahydropyrimidine, mp.

1 47 ° C; 2- [[4- (3,5-dimethyl If enoxy) phenyl] imino-hexahydropyrimidine, mp 145 ° C; 2- (4-n-propylphenyl) imino-hexahydropyrimidine, mp. 110 ° C; 2- (4-n-octyphenyl) imino-hexahydropyrimidine p-dodecylbenzene sulfonate, oil; 2- (4-tert-butylphenyl) imino-hexahydropyrimidine, m.p. 180 ° C; 15 I 2- [4- (2,5-dimethylphenoxy) phenyl-jimino-hexahydropyrimidine, I m.p. 148 ° C; 2- (4-cyclohexyphenyl) imino-hexahydropyrimidine benzothiazole thiolate, m.p. 16 9 0 C; 2- (4-adamantylphenyl) imino-hexahydropyrimidine, mp. 226 ° C; 2- [4- (2- (2-n-butoxyphenyl) ethyl] phenyl] imino-hexahydropyrimidine, m.p. 1 1 00C; and 2- (4-isopropylphenyl) imino-hexahydropyrimidine, m.p. 134 ° C.

The new substances have been prepared according to one of the methods described in the aforementioned Dutch patent application 7711390.

In the preparations according to the invention, the active substance is mixed with solid carrier material, or dissolved or dispersed in liquid carrier material, optionally in combination with auxiliary substances, such as emulsifiers, wetting agents, dispersants and stabilizers.

Examples of preparations according to the invention are aqueous solutions and dispersions, oil solutions, and oil dispersions, solutions in organic solvents, pastes, dusting powders, dispersible powders, miscible oils, granules, pellets, invert emulsions, aerosol pre- 78 1 0 3 5 0 t: -7-; PHN 9262 ______ i readings and smoking candles.

I Dispersible powders, pastes and miscible oils are concentrate formulations which are taken before or during! the use must be diluted, 5 I The invert emulsions and solutions in organic solvents are mainly used in air application, namely when large surfaces are treated with a relatively small amount of preparation. The invert emulsion can be used in the Spraying equipment is prepared by emulsifying water in an oil solution or an oil dispersion of the active substance.

The solutions of the active substance in organic solvent; can be provided with a phytotoxicity-reducing! fabric, such as wool grease, wool fatty acid, or wool grease alcohol.

15; Some preparation forms are explained in more detail below by way of example.

Granular preparations are prepared by, for example, incorporating the active substance in a solvent I, t or dispersing it in a diluent and optionally impregnating the obtained solution / suspension on granular support material such as porous granules (eg pumice stone) in the presence of a binder. and attaclay), mineral non-porous granules (sand or ground marl), organic granules (eg dried coffee grounds, cut tobacco stalks and ground corncob waste). A granular preparation can also be produced by compressing the active substance together with powdered minerals in the presence of lubricants and binders and disintegrating and sieving the compress to the desired grain size. Granular preparations can be manufactured in another way by mixing the powdered active substance with powdered fillers, and then glumulating the mixture with liquid to the desired particle size.

Dusting powders can be obtained by intimately mixing the active substance with an inert solid powder. drage-rmate-rianai ^ - such as eg -; - fc-a-Hc -: ----— —— 78 1 0 3 5 0 -8- PHN 9262 _; -

Dispersible powders are prepared by mixing 10 to 80 parts by weight of a solid inert carrier such as, e.g., kaolin, dolomite, gypsum, chalk, bentonite, attapulgite, colloidal Si09 or mixtures of these and similar substances, with 5 to 80 parts by weight of the active substance, 1 to 5 parts by weight of a dispersant such as, for example, the lignin sulfonates or alkyl naphthalene sulfonates known for this purpose, preferably also 0.5 to 5 parts by weight of a wetting agent such as fatty alcohol sulfates, alkylaryl-10 sulfonates, fatty acid condensation products, or polyoxyethylene compounds, and finally other additives if desired.

For the preparation of miscible oils, the active compound is dissolved in a suitable solvent which is preferably poorly miscible with water and one or more emulsifiers are added to this solution. Suitable solvents are e.g. higher alcohols such as lauryl alcohol, decanol and octanol, xylene, toluene, petroleum distillates rich in aromatics, e.g. solvent naphtha, distilled tar oil and mixtures of these liquids. As emulsifiers, for example, polyoxyethylene compounds and / or alkyl aryl sulfonates can be used. The concentration of the active compound in these miscible oils is not limited and can vary, for example, between 2 and 50% by weight.

In addition to a miscible oil, a liquid and highly concentrated primary composition can also be mentioned a solution of the active substance in a water-miscible liquid, eg a glycol, or glycol ether, to which solution a dispersant and optionally a surface -active substance has been added 30. Dilution with water shortly before or during spraying results in an aqueous dispersion of the active substance.

An aerosol preparation according to the invention is obtained in the usual way by incorporating the active substance, optionally in a solvent, into a 78 1 0 3 5 0 -9-PHN 9262 using propellant gas. volatile liquid, such as, for example, a mixture of chlorofluorinated derivatives of methane and ethane, I a mixture of lower hydrocarbons, dimethyl ether, or gases such as carbon dioxide, nitrogen and nitrous oxide.

Smoke candles or smoking powders, ie preparations that can generate smoke while burning a pesticide, are obtained by incorporating the active substance in a flammable mixture, which, for example, can contain as fuel a sugar or a wood, preferably in ground form, a substance to maintain combustion, such as, for example, ammonium nitrate or potassium chlorate, and further, a substance to delay combustion, eg, kaolin, bentonite and / or colloidal silica. acid..

i I In addition to the above ingredients, 15! the agents according to the invention also other for use! m contain such substances known substances.

For example, a lubricant such as calcium or magnesium stearate can be added to a dispersible powder or a mixture to be granulated. Also, for example, "adhesives" such as polyvinyl alcohol cellulose derivatives or other colloid-like materials, such as casein, may be added to improve the adhesion of the composition to the crop. Furthermore, a substance can be added to reduce the phyto-toxicity of active substance, carrier material or auxiliary substance, such as wool fat or wool fatty alcohol 1.

The preparations according to the invention may also include growth regulators and pesticide compounds known per se. This broadens the spectrum of action of the preparation and can cause synergies.

In addition, foliar fertilizers may be present.

The following growth regulators known per se, herbicide, fungicide, nematicide, insecticide and acaricidal compounds are suitable for use in such a combination preparation.

78 1 0 3 5 0 -10- PHN 9262_

Growth regulators such as: 1. higher alcohols, eg octanol and decanol; 2. lower ester of fatty acids; 3. ethylene generators, e.g. (2-chloroethyl) phosphonic acid and 5 I 2-chloroethyl-tris (2-methoxyethoxy) silane; Nitrodiphenyl ethers; 5. substituted dinitroanilines; 6. trifluoromethylsulfonylamino compounds; 7. piperidine derivatives; 10 and further male hydrazide; 2,3: 4,6-di-O-isopropylidene -C-oxylo-2-hexulo-furanosonic acid sodium; N-, N-dimethylamino-succinic acid; The cyclopropyl-4-methoxy-ai- (pyrimidin-5-yl) benzyl! alcohol; 2-chloroethyl trimethyl ammonium; N, N-di (phosphono-methyl) glycine; 9-hydroxyfluorene-9-carboxylic acid (or ester); 2-chloro-9-hydroxyfluorene-9-carboxylic acid (or ester); N-1-naphthyl, phthalamic acid, and 2,3-dihydro-5,6-diphenyl-1,4-oxathiine, or mixture of these compounds.

Herbicides such as; S-propyl butylethylthiocarbamate; N- (1-ethylpropyl) -2,6-20-dinitro-3,4-xylidine; Ν, Ν-dimethyldiphenyl acetamide; 4-isopropyl-2,6-dinitro-N, N-dipropylaniline; and N, N-diethy1-2-- (1-naphthalenyloxy) propanamide; or mixtures of these compounds.

Fungicides such as: 1. organic tin compounds, eg triphenyltin hydroxide and triphenyltin acetate; 2. alkylene bis dithiocarbamates, e.g. zinc ethylene bis dithio carbamate and manganese ethylene bis dithiocarbamate; 3.1-acyl or 1-carbamoyl-N-benzimidazole (-2) carbamates and 1,2-bis (3-alkoxycarbonyl-2-thiureido) benzene, and 2,4-dinitro-6- (2- octylphenyl) crotonate, 1-bis (dimethylamino) phosphoryl] -3-phenyl-5-amino-1,2,4-triazole, N-trichloromethylthiophthalimide, N-trichloromethylthiotetrahydrophthalimide, N- (1,1,2 , 2-tetrachloroethylthio) -tetrahydrof-35 taalimide, N-dichlorofluoromethylthio-Nf eny1-N, N * -dimethylsulfamide, tetrachloroisophthalonium tril, thiazolyphenzimida - 78 1 0 3 5 V. * § * ". -11- * PHN 9262.-1: -sole, 5-butyl-2-ethylamino-6-methylpyrimidin-4-yl-dimethyl-sulfamate, 1- (4-chlorophenoxy) -3,3-dimethyl-1 ( 1,2,4-triazole-1-yl) -2-butanone, ei- (2-chlorophenyl) -t * - (4-chlorophenyl) -5-pyrimidine methanol, 1- (isopropylcarbamoyl) -3 "(3, 5-dichlorophen-5-yl) hydantoin, N- (1,1,2,2-tetrachloroethylthio) -4-cyclohex- 1-1,2-carboximide, N-trichloromethylmercapto-4-cyclohexene-! -1 2-dicarboximide, N-tridecyl-2,6-dimethylmorpholine, and acylalanine, or mixtures of these compounds ngen.

10] Nematicides such as: 1. Carbamates, eg 2-dimethylamino-5,6-dimethylpyrimidin-4-yl dimethyl carbamate, 2-isopropoxyphenyl methyl carbamate, and 2,3-dihydro-2,2-dimethyl benzofuran-7-yl methyl carbamate ; ! 2. phosphorothioates, e.g., O-athyl S, S-dipropyl phosphorodithioate, 15: 0,0-dialkyl 0-4-nitroenyl phosphorothioate and 0,0-diethyl 4-4 -methylsulfinylphenyl phosphorothioate; ; and further 2-methyl-2- (methylthio) propionaldehyde 0-methyl- carbamoyloxim, and 1,3-dichloropropene; I or mixtures of these compounds.

Insecticidal including aphicides such as: 1. organic chlorine compounds, eg 6,7,8,9,10-hexaehloro-1,5,5a, 6,9,9a-hexahydro-6,9-methano-2,4, 3-benzo [e]] -dioxa-thiepine 3-oxide; 2. carbamates, eg 2-dimethylamino-5,6-dimethylpyrimidin-4-25-yl dimethyl carbamate, 1-naphthyl methyl carbamate, 2-isopropoxyphenyl methyl carbamate and 2,3-dihydro-2,2-dimethylbenzo furan -7-yl-methyl carbamate; 3.di (m) ethylphosphates, e.g. 2-chloro-2-diethylcarbamoyl-1-methylvinyl -, 2-methoxycarbonyl-1-methylvinyl -, 30l-methyl-2-methylcarbamoylvinyl -, 2-chloro-1- ( 2,4-dichlorophenyl) vinyl, 2,2-dichlorovinyl, and 2-chloro-1- (2,4,5-trichlorophenyl) vinyl di (m) ethylphosphate; 4. 0.0-di (m) ethyl phosphorothioates, eg 0 (S) -2-methylthioethyl -, S-2-ethylsulfinylethy1 -, S - 2 - (1-methylcarbamoylethylthio) ethyl —0- 4-bromo-2,5-dichlorophenyl _, ______; _ / ______1 78 1 0 3 5 0 / -12- PHN 9262____ 0-3,5,6-trichloro-2-pyridyl -, 0-2-isopropyl-6 methyl-pyrimidin-4-yl -, 0-4-methylsulfinylpheny1 -, and 0-4-nitrophenyl-0,0-di (m) ethyl phosphorothioate; 5. 0.0-di (m) ethyl phosphorus thioates, eg S-methylcarbamoy 1-y 5 y methyl-, S-2-ethylthioethyl-, S- (3,4-dihydro- 4-oxo-benzo [d] -1,2,2-triazin-3-ylmethyl) -, S-1,2-di (ethoxycarbonyl) ethyl, S-6-chloro-2-oxobenzoxazolin ** 3-ylmethyl-, and S-2,3-dihydro-5-methoxy-2-oxo-1,3,4-thiadiazol-3-ylmethyl 0,0-di (m) ethyl phosphorodithioate; 6. Phosphonates, eg dimethyl 2,2,2-trichloro-1-hydroxyethyl phosphonate; and further J-ethyl S, S-dipropyl phosphorodithioate; S-methyl N- (methylcarbamoyloxy) thioacetamidate; 0, S-dimethyl acetylphosphoramidathioate; and 0-ethyl-5-phenyl ethylphosphonodithioate; Or mixtures of these compounds.

Acaricides such as: 1. organic tin compounds, eg tricyclohexyItin hydroxide and di [tri- (2-methyl-2-phenylpropyl) tin ^ oxide; 2. organic halogen compounds, eg isopropyl 4,4'-di-bromobenzzilate and 2,2,2-trichloro-1,1-di (4-chlorophenyl) ethanol; and further: 3-chloro-ethoxyimino-2,6-dimethoxybenzyl benzoate and 0,0-dimethyl S-methylcarbamoylmethyl phosphorothioate; or mixtures of these compounds.

The dosage of the preparation according to the invention desired for practical application will depend, inter alia, on the selected active substance, the preparation form, the type of crop to be treated, the state of the crop and the weather conditions. In general, favorable results are obtained with a dosage corresponding to 100-5000 g of the active substance per hectare.

This dosage can be applied in one go, but also by means of a multiple spray.

The invention will be explained in more detail below with reference to the following exemplary embodiments.

78 1 0 3 5 0 -13-! EXAMPLE 1 I 2.5 g of Alkylphenylpolyoxyethylene and 2.5 g of a mixture of an alkylphenyl sulfonate and a polyoxyethylene compound were dissolved in 3 liters of acetone. This solution was used as a solvent for the active substances. The amount by weight of active substance required for the desired concentration - see Table 1 - was dissolved in 2 ml of the above solvent.

To the solution thus obtained, 18 ml of water was added just before spraying. If the active substance did not dissolve in the above solvent, the compound was dispersed in the solvent after being ground.

In the greenhouse, young tobacco plants of 9 weeks old were sprayed with the preparations obtained; the tops of the plants were removed six days before spraying. The top side shoots were up to about 0.6 cm long when spraying. Three plants were used per concentration, of which only the side shoots, leaf feet and stem were sprayed.

Two weeks after spraying, the effectiveness of the active substances was determined by determining whether, and if so to what extent, the side shoots had been inhibited in their development. The results of this assessment are shown in Table 1, using the following valuation: no effect + _ = weak growth inhibition + = strong growth inhibition 25 ++ = very strong effect; the side shoots have been killed 78 1 0 3 5 0 -14- PHN 9262 -! TABLE 1 j assessment of the

j cone, in side-shoot inhibiting active substance mg / l action _ 2- (4-n-hexylthiophenyl) imino-1000 + hexahydropyrimidine 750 + 500 + 250 t 1-methyl-2- (4-n-hexylphenyl) - 1000 + 10 imino -hexahydropyrimidine 750 500! 2- (4-n-hexylphenyl) imino-hexa-1000 ++ hydropyrimidine 750 ++ 500 + + 15 250 ++ J2- (4-n-heptylphenyl) imino-hexa- 1000 + + hydropyrimidine 750 ++! 500 ++! 250 ++ 20; 2- 4- (2-phenylethyl) phenyl imino-1000 + + -hexahydropyrimidine 750 ++ 500 ++ 250 + + 2- (4-n-nonylphenyl) imino-hexa 1000 + + 25 hydropyrimidine 750 ++ 500 ++ 250 + 2- (4-n-hexylthiomethylphenyl) - 1000 + imino-hexahydropyrimidine 750 £ 30 500 2 "[4- {2- (4-methylphenyl) ethyl] -1000 + phenyl] imino-hexahydropyrimidine 750 + 500 t 250 35 2- (4-sec.butylthiomethylphenyl) - 1000 + imino-hexahydropyrimidine 750 £ 500 2- (4-isopentylthiophenyl) imino-1000 + hexahydropyrimidine 750 + 40 500 t 250 r 2- (4-n-pentylphenyl ) imino-hexa- 1000 ++ hygropyrimidine 750 ++ 500 + --2 ^ 0-- ± - 78 1 0 3 5 0 -15- PHN 9262________ (continued Table 1)! I 'assessment of the

! . ® j conc. in side shoot inhibiting! active substance mg / 1 effect j 111 11 rr "- - '' 1" _ «'" r "5 {2- (4-n-hexyloxyphenyl) imino- 1000 +

Ihexahydropyrimidine 750 + 500 + 250 2- (4-n-octylphenyl) imino-hexa-1000 ++ 10 hydropyrimidine 750 ++ 500 + 250 f '2- (4-n-octylphenyl) imino-hexa 1000 + +! hydropyrimidine acetate ί 750 + 15! ! 500 f! I 250 f! 2- (4-n-octyloxyphenyl) imino-hexa-1000 ihydropyrimidine i 1-methyl-2- [4- (1-methylheptyl) - | 1000 20thiophenyl] imino-hexahydropyrimi-jdine j j2- [4- (1-methylbuty 1) phenyl] imino-j 1,000 jhexahydropyrimidine j j2- [4- (1-methylbutyl) thiophenyl] - | 1000 + 25 jimino-hexahydropyrimidine * 2 2- [4- (1-methyl-hexyl-1) thiophenyl]; 1,000+ imino-hexahydropyrimidine; j2- (4-n-octylphenyl) imino-4-met-j 1000 ihy1-hexahydropyrimidine j 30 2- [4- (4-chlorobenzyloxy) phenyl] -1000 + imino-hexahydropyrimidine 2- [4- (4- methylphenoxy) phenyl] 1000 imino-hexahydropyrimidine 2 ”[4- (4-chlorobenzyloxy) phenyl] 1000 imino-hexahydropyrimidine 2- (4-n-heptylphenyl) imino-imi 1000. £ dazoline 2- (3.4 -tetramethylenphenyl) 1000 + imino-hexahydropyrimidine 40 2- [4- (2-chloroallylthio) phenyl] 1000 + imino-hexahydropyrimidine 2- [4- {2- (2-methylphenyl) ethyl] 1000 ++ phenylimino-hexahydropyrimidine ______ 78 1 0 3 5 0 -16- PHN 9262 _________: -—! (continued table 1) I assessment of the

I conc. in i side-shoot inhibiting active substance mg / 1 action_ 5 2- 4- (2-furylethy1) phenyl imi-1000 + no-hexahydropyrimidine I 2-C4- / 2- (4-isopropoxyphenyl) 1000 ++ ethylphenyl] imino-hexahydropyrimidine 10 2 - [4- (2- (4-chlorophenyl) ethyl] 1000 ++ phenyl] imino-hexahydropyrimidine 2- [4-i2- (4-isopropylphenyl) ethyl} 1000 ++ j phenyl] imino-hexahydropyrimidine J2- [4 - {2- (4-ethoxyphenyl) ethyl] 1000 + * 3 j phenyl] imino-hexahydropyrimidine 2- [4- {2- (2-n-butoxy phenyl) ethyl] 1000 phenyl] imino-hexahydropyrimidine j EXAMPLE 2

In a manner similar to that described in Example 1, 20 preparations of 20 mg of 2- (4-n-h -exylphenyl) imino-hexahydropyrimidine as active substance were dissolved in the amounts of solvent indicated in Table 2; as the solvent, the solvent described in example 1 was used. The solution were.

supplemented with the amounts of water shown in Table 2.

25

Young tobacco plants were treated in a similar manner as in Example 1 and after 2 weeks the result was evaluated; the results are shown in table 2.

TABLE 2 Assessment of the

30.

amount of conc. act. side shoot inhibiting solvent__hydrogen- in mg / 1__effect__ 2 ml 18 ml 1000 ++ 5 ml 15 ml 1000 ++ 10 ml 10 ml 1000 ++ 20 ml 0 ml J000 ++ 35 78 1 0 3 5 0 '\ -17- PHN 9262 I' The same result was obtained when 20 ml of pure acetone I was used instead of 20 ml of solvent.

EXAMPLE 3 5 g of polyoxyethylenated castor oil was dissolved in 3 liters of acetone. 20 mg of 2- (4-n-Hexyloxyphenyl) imino-hexahydropyrimidine as active substance were dissolved in 2 ml of the above solvent and 18 ml of water were added.

With the preparation thus obtained, young tobacco plants were treated as described in Example 1; after 2 weeks, the result was assessed and valued as'. +.

EXAMPLE 4 I Adult tobacco plants - against flowering - were sprayed in the field (with preparations prepared as indicated in Example 11). Before spraying, the tops of the plants were removed. Two weeks after spraying, the activity of the active substances evaluated as described in Example 1. The results shown in Table 3 were obtained.

j TABLE 3 I (assessment of the

20 y conc. in · side shoot remmendo _ active substance mg / 1 y effect 2- (4-n-propylphenyl) imino-hexa- 1000 £ hydropyrimidine 750 2- (4-n-pentylphenyl) imino-hexa 1000 ++ 25 hydropyrimidine 750 + 500 ± 2 - (4-n-hexylphenyl) imino-hexa-1000 ++ hydropyrimidine 750 ++ 500 + + 30 2- (4-n-heptylphenyl) imino-hexa-1000 ++ hydropyrimidine 750 ++ 500 + 2- (4- n-nonylphenyl) imino-hexa- 1000 £ hydropyrimidine 750 £ 35 500 £ 2- (4-n-hexy lo'xy pheny 1) imino- 1000 £ hexahydropyrimidine 750 £ 500 1 78 1 0 3 5 0 0 -18- PHN 9262_ EXAMPLE 5

Mature tomato plants were sprayed with solutions of the actives listed in Table 4 in a water-acetone mixture (9Π) at the indicated concentrations. Three weeks after spraying, the effectiveness of the active substances was determined by examining whether, and if so to what extent, the bud and lateral shoots were inhibited in their development. The results are shown in Table 4, using the valuation from Example 1.

10 TABLE 4 I conc. in growth inhibiting work.

active substance mg / l top side shoots 2- (4-n-hexylphenyl) imino-hexa-3000 ++ ++ hydropyrimidine 1000 ++ + 15. 300 2- (4-n-pentylphenyl) imino-hexa-3000 + ++ hydropyrimidine 1000 ++ ++ 300 2- (4-n-heptylphenyl) imino-hexa-3000 + ++ 20 hydropyrimidine! 1000} + + 300 t 2- (4-cyclohexyiphenyl) imino- 3000 ++ ++ hexahydropyrimidine 1000 £ + 300 25 2- (4-n-hexylthiophenyl) imino- 3000 ++ ++ hexahydropyrimidine 1000 + £ 300 - 2 - (4-n-hexyloxyphenyl) imino- 3000 ++ ++ hexahydropyrimidine 1000 + + 30 300 EXAMPLE 6 Growth inhibition tomato

3 week old young tomato plants were watered with solutions of 2- [4- (1-methylfc.eptylthio) phenyl] imino-hexahydro-pyrimidine as active substance in a mixture of water and acetor (9: 1). After three weeks, growth was compared to non-budger plants. The growth inhibition was valued as follows: 78 1 0 3 5 0

V

-19- PHTST Q262 ___: ----— j - * no growth inhibition _ + = very low growth inhibition.

j + = slight growth inhibition ++ = pronounced growth inhibition.

j +++ = Very strong growth inhibition j The following results were obtained: 5 j TABLE 5 dosing in kg / ha growth inhibition 3 ++ + 1 ++ + 0.5 + + 10 EXAMPLE 7

Growth inhibition ornamental plants. ; A solution of 10 g of active substance, 8 g of alkylbenzene polyoxyethylene and 15 ml of cyclohexanone in 57 ml of xylene was emulsified in water in an amount of 10% by volume. Poinsettia 15 µ and chrysanthemum-p1 anten were sprayed with this solution in the dosages shown in Table 6. The results below i ...

were obtained, using the rating shown in Example 6.

TABLE 6 20 dosing in growth inhibition _ active substance kg / ha__Poins. Chrys.

2- (4-isopropylphenyl) imino- 2 - + + + hexahydropyrimidine 3 - ++ 0,5 - + 25 2- (4-cyclohexylphenyl) imino- 2 + + + hexahydropyrimidine 1 + 0,5 2- (4 -n-butylphenyl) imino- 4 +++ hexahydropyrimidine 2 +++ 78 1 0 3 5 0

Claims (11)

1. A growth-regulating composition, characterized in that the preparation contains, in addition to a solid or liquid inert carrier material, a compound of the general formula 78 1 0 3 5 0 λ -2 1- 1- 9262 _________ ί * 3 I CH2 I R1 ~ \ / -N = te <\ ^ "^ CE2yn ί / N - · CE ^ I E2 IIV 15 where Rj is an alkyl, alkenyl, halogen or unsubstituted alkoxy, alkenyloxy, alkylthio, alkenyl * thio, alkoxyalkyl or alkylthioalkyl group of 3 to 12 carbon atoms, a mono-, bi- or tricycloalkyl group of 3 to 12 carbon atoms, a phenyl, phenoxy- , phenylthio, phenylalkyl, phenylalkoxy or phenylalkylthio group having 6 to 10 carbon atoms, which phenyl group or whose phenyl group is optionally substituted with halogen or with alkyl, alkoxy, j or alkylthio, which alkyl, alkoxy or alkylthio - groups have from 1 to 6 carbon atoms and may optionally be halogenated, or a furylalkyl or thienylalkyl group with 5 to 8 carbon atoms and -15 represents, & 2 is a hydrogen or halogen atom, or wherein R 1 and R 2 together represent a trimethylene or tetramethylation group, R 1 and are the same or different and a hydrogen or an alkyl or alkanoyl group having 1 to 4 carbon atoms, R 1 is a hydrogen atom or an alkyl group of 1 to 4 carbon atoms, and n is 0 or 1, 25 or a salt or complex thereof. Preparation according to claim 1, characterized in that the preparation as active substance comprises a compound of the general formula 78 1 0 3 5 0 -22-PHN 9262-β & NH-CH9 e; - <^ Λ n-c (^ / cb2 N> ==== ^ NH - CH2 wherein R 1 represents an n-alkyl group of 5 to 9 carbon atoms or a phenylethyl group, or a salt or complex thereof. Preparation according to claim 2, characterized in that the preparation contains as active substance 2- (4-n-pentyl-phenyl) imino-hexahydropyrimidine or a salt or complex thereof. 4. A composition according to claim 2, characterized in that the active substance composition contains 2- (4-n-hexyl-Ifenyl) imino-hexahydropyrimidine or a salt or complex I thereof, 5. A composition according to claim 2, characterized in that the active substance composition contains 2- (4-n-heptyl-phenyl) imino-hexahydropyrimidine or a salt or complex thereof. 6. A composition according to claim 2, characterized in that the active substance composition contains 2- (4-n-octy1-phenyl) imino-hexahydropyrimidine or a salt or complex thereof. Preparation according to claim 2, characterized in that the active ingredient composition contains 2- (4-a-nonylphenyl) imino-hexahydropyrimidine or a salt or complex thereof. Preparation according to Claim 2, characterized in that the active substance contains 2 - (^ 4- (2-phenylethyl) phenyl-jimino-hexahydropyrimidine) or a salt or complex thereof. 9. Process for the preparation of a composition with a growth-regulating effect, characterized in that the compound is incorporated into the carrier in one of the four or inert carriers. 0 3 5 0: -2 3- '. St \ St * ΡΗΝ 9262______ general formula! * 3 i V Ν - CE! ΓΛ / \ 'Λ- / γ / R, Ν CH IIV * 5 i: where Rj, Rl, Rl> Rl, Rl and n have the meaning given in claim 1, or a salt or complex thereof, ! 5 optionally with the addition of other growth regulators, pesticides, foliar fertilizers and / or adjuvants such as humidifiers, emulsifiers, dispersants and stabilizers. 10. Method for regulating the growth of plants or plant parts in agriculture and horticulture, characterized in that the crop concerned is treated with a preparation according to any one of claims 1 to 8 in a dosage corresponding to 100 to 5000 g active substance per hectare. 11. Method for inhibiting or preventing the development of side shoots in agricultural and horticultural crops, characterized in that the crop in question is treated with a preparation according to any one of claims 1 to 8 in a dose; which corresponds to 100 to 5000 g of active substance per hectare. 781 03 50