AU592494B2 - Agents for regulating plant growth - Google Patents
Agents for regulating plant growth Download PDFInfo
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- AU592494B2 AU592494B2 AU13551/88A AU1355188A AU592494B2 AU 592494 B2 AU592494 B2 AU 592494B2 AU 13551/88 A AU13551/88 A AU 13551/88A AU 1355188 A AU1355188 A AU 1355188A AU 592494 B2 AU592494 B2 AU 592494B2
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing aromatic radicals
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds
- A01N57/28—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds containing acyclic or cycloaliphatic radicals
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- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
592494 Form COMMONWEALTH OF AUSTRALIA PATENTS ACT 1952-69 COMPLETE SPECIFICATION
(ORIGINAL)
Class Application Number: Lodged: IopiVplete Specification Lodged: Accepted: r Published: Pliority: I nt. Class Re 14ted Art: This document coatairi the amcndrieits nmade unc,.-r Section 49 and is correct for printing, 4 Nalme of Applicant: Address of Applicant: Actual Inventor; Address for Service BASF AKTIENGESELLSCHAFT D-6700 Ludwigshaf en, Federal Republic of G3ermany EBERHARD PETER SCHOTT, MAX LUIB, PETER HOEPPNER, HANS LANG, KLAUS SCH-ELBERGER, HUBERT SAUTER and ERNST BUSCHMANN EDWD. WATERS SONS, 50 QUFEN STREET, MELBOURNE, AUSTRALIA, 3000.
Complete Specification for the nlnzuon entitled: AGENTS FOR REGULATING PLANT GROWTH The following statement is a full description of this Invention, Including the best method of performing it known to us BASF Aktiengesellschaft 0.Z. 0050/39048 Agents for regulating plant growth The present invention relates to agen~ts for regulating plant development which contain a mixture of active ingrediants, and methods of regulating plant development with these agents, The u! t of bioregulatory triazoles, quaternary ammnonium compounds, e.g., N,N-dimethylpiperidinium salts (DE-OS 22 07 575) and phosphonic acid derivatives, e.g. 2-chloroethylphosphonic acid and salts thereof 1(DE-AS 16 67 968) for regulating plant developm~ent have been disclosed. it is also known to employ mixtures or salts of N,N,N-trimethyl-N-2-chloroethylammonium compounds or NN-dimethylpiperidiniun compounds and 2-chloroethanephosphonic acid for regulating plant development (DE-OS 23 61 410, DE-OS 24 22 807, German Patent 27 55 940).
~8'15 We have now found that a composition of a triazole compound having a growth-regulatory action of the general formula Ia, 1b, Ic or Id
OH
A. (CH2) R I
A
"N
A
A".O-ICH2)
R
n Ic
N
BASF Aktiengesellschaft 2 O,Z, 0050/39048 C3H O H A>KK 0C3 N-N, I d
N
A denoting unsubstituted phenyl or pheniyl substituted by CI-C4-alkyl, C1-C 4 -alkoxY or CF 3 and R denoting tert.-butyl or the group
CH
3 Swhere R2 is hydrogen, methyl or ethyl, t: v and either a quaternary thianium or ammonium salt selected from the group consisting of NN-dimethylazacycloheptanium salts, N,N-dimethylpiperidinium salts, N,N-dimethylhexahydropyridazinium salts, N,N-dimethyltetra- 'Vhydropyridazinium salts, N-methylpyrdu slNN-dimethylpyrrolidium t n ,-riehl---hootyamnu salt and/or a phosphonic I ic acid, 2-chloroethylaminoethylphosphonic acid, 2-chloroethylaminobutylphosphonic acid, 2-chloroethylphos phonic acid-N,N-dimethiylamide, 2-chloroethylphosphonic ai--qtyamdvi,lphosphol~ic acid, propylphos phonic ,acid, phosphonomethylglycineA and benzylphophonic acid, or the compound 5-4clrpey)3459 ~etaattacco54101,8llo deca-'3,9-diene are particularly well suited~ for regulating plant development, as a synergistic effect is obse.zved.
The composition may contain, in addition to the triazole compound, active ingredients from several of the abovementioned classes of other compounds.
In formulae Ia to Id, A is substituted or unsubstituted phenyl, Examples of substituents are halogen, such as fluorine, chlorine, bromine or iodine, C 1 -Ct4-alkyl or Ci-C4-alkoxy, methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl or the corresponding alkoxy radicals, and CF 3 The phenyl radical may bear one or more, preferably 1 to 3, identical or different substituents, Preferably, A denotes phenyl, 2,4dichlorophenyl, 4-trifluoromethylphenyl or 4-methylphenyl.
A.
x
A
1 4 /1
I~~
i; i BASF Aktiengesellschaft 0.Z. 0050/39048 In formula Ic, n is 2, 3, 4 or 5, and especially 2; The manufacture of the prior a' triazole compounds la to Id is disclosed in European Applications 44 407, 40 350, 43 923 and 56 087.
By thianium and ammonium salts we mean salts of an inorganic or organic, but not phytotoxic, acid. Preferably, halides such as bromides and especially chlorides are used.
Particularly mixtures of one or more triazoles, for example 1-(2,4-dichlorophenyl)-1-methyl-2-methoxy-2-(1H-1 ,2,4-triazol-1-yl)-ethanol; 1-phenoxy-3-(1H-1,2,4-triazol-1-yl)-4-hydroxy-5,5-dimethylnexane; a 1-(4-trifluoromethylphenyl)-2-(1,2,4-triazol-1-yl)-3-(5-methyl-1,3-dioxan- 5-yl)-propen-3-ol; 1-(2-ethyl-5-methyl-1,3-dioxan-5-yl)-2-(1,2,4- ,15 triazolyl-(1))-3-(4-methylphenyl)-propan-l-ol with a 5-(4-chlorophenyl)- 3,4,5,9,10-pentaazatetracyclo[j,4,1,02'6,08,11]dodeca-3,9-diene,
N,N,N-
trimethyl-N-2-chloroethylammonium chlorid6, N,N-dimethylpiperidinium chloride and/or 2-chloroethylphosphonic acid have a good developmentregulating action on plants.
0# The ratio of the active ingredients may vary within wide limits, for example from 30:1 to 1:30, preferably from 10:1 to 1:25 parts by weight of the triazole compound, based on the additional active ingredient(s) in the composition.
Examples of plant-regulatory effects are: inhibition of cell elongation, in stems and stalks, and branches and trunks. The stem wall is strengthened, inducing rigor resulting in :30 firmer and stronger plants which are necessary for ensuring yields in 4 t cereals and other graminaceous crops, oilseeds, legumes, fibrous plants and tie crops, and making work easier and closer planting possible; improvement in the cultivation of young plants as a result of the more compact growth form; compact growth of ornamentals, making for economical production of better quality plants; improvement in the resistance to heat, cold, water deficiency and salts; BASF Aktiengesellschaft 4 O.Z. 0050/39048 improving fruiting, for example in pomes, drupes and multiple fruit, cotton, soybeans, vines, citrus fruit, almonds, olives, cocoa and coffee; specific sex differentiation with a view to raising yields, in cucurbits and papaya; promotion of senescence or of the formation of separation layers for ready abscission, reducing the adherence of fruit, facilitating the mechanical harvesting of citrus fruit, pomes, drupes and multiple fruit, olives, almonds, coffee and dry indehiscent fruit; defoliation of trees, bushes, shrubs and ornamentals for shipment from nurseries in the fall; defoliation of trees to interrupt the chain of parasite infection, Gloeosporium heveae in Hevea brasiliensis; hastening ripening, in tomatoes, citrus fruits, pineapples, other fruit varieties and coffee, with the aim of programing harvesting and promoting color in fruit, or in the case of cotton of concentrating harvesting to at most two pickings and interrupting the chain of nutrition for injurious insects; increasing yields as a result of more favorable development conditions optimum micro-climate in the stand and/or utilization of water and/or nutrients).
The new compositions, or the various active ingredients applied in sequence, have a synergistic action, particularly in cereals Oil plants and legumes, the action of the compositions, or of the active fngredients applied in sequence, is greater than the combined actions of the individual active ingredients. They are also better tolerated by crop plants than prior art active ingredients, Either the composition may be applied, or the individual components of the combination one after the other. The plants may be treated with the agents in the form of seed dressings, postemergence soil treatments, or the agents may be used for treating cuttings and plant parts at every development stage of the plant from dormancy to ripening a nd senescence.
IIL---l BASF Aktiengesellschaft 5 O.Z. 0050/39048 The agents may be applied for instance in the form of directly sprayable solutions, powders, suspensions (including high-percentage aqueous, oily or other suspensions), disper'ions, emulsions, oil dispersions, pastes, dusts, broadcasting agents, or granules by spraying, atomizing, dusting, broadcasting or watering. The forms of application depend entirely on the purpose for which the agents are being used, but they must ensure as fine i a distribution of the active ingredients according to the invention as possible.
For the preparation of solutions, emulsions, pastes and oil dispersions to be sprayed direct, mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, further coal-tar oils, and oils of S vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons S such as benzene, toluene, paraffin, tetrahydronaphthalene, alkylated S15 naphthalenes and their derivatives such as methanol, ethanol, propanol, 0 0 butanol, chloroform, carbon tetrachloride, cyclohex'nol, cyclohexanone, chlorobenzene, isophorone, etc., and strongly polar solvents such as Sdimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, water, etc.
are suitable.
Aqueous formulations may be prepared from emulsion concentrates, pastes, oil dispersions or wettable powders by adding water. To prepare Omulsions, j pastes and oil dispersions the ingredients as such or dissolved in an oil or solvent may be homogenized in Water by means of wetting or dispersing I agents, adherents or emulsifiers. Concentrates which a;e suitable for dilution with water may be prepared from active ingredient, wetting agent, adherent, emulsifying or dispersing agent and possibly solvent or oil.
Examples of surfactants are; alkali metal, alkaline earth metal and ammonium salts of ligninsulfonic acid, naphthalenesulfonic acids, phenolsulfonic acids, alkylaryl sulfonates, alkyl sulfates, and alkyl sulfonates, alkali metal and alkaline earth metal salts of dibutylnaphthalensulfonic acid, lauryl ether sulfate, fatty alcohol sulfates, alkali metal and alkaline earth metal salts of fatty acids, salts of sulfated hexadecanols, hptadecanols, and octadecanols, salts of sulfated fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyeyethylene octylphenol ethers, ethoxylated isooctylphencl, ethoxylace octylphenol and ethoxylated nonylphenol, alkylphenol polyglycol ethers, 't'ibutylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esl:ers, lignin, sulfite waste liquors and methyl cellulose.
BASF Aktiengesellschaft 6 0.Z. 0050/39048 Powders, dusts and broadcasting agents may be prepared by mixing or grinding the active ingredients with a solid carrier.
Granules, coated, impregnated or homogeneous granules, may be prepared by bonding the active ingredients to solid carriers. Examples of solid carriers are mineral earths such as silicic acid, silica gels, silicates, talc, kaolin, attapulgus clay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, and ureas, and vegetable products such as grain flours, bark meal, Wood meal, and nutshell meal, cellulosic powders, etc.
J
t The formulations contain from 0.1 to 95, and preferably 0.5 to 90, X by weight of active ingredient, There may be added to the compositions oils of various types, fungicides, S nematocides, insecticides, bactericides, trace elements, fertilizers, spreader-stickers, and anti-foams for preventing side-effects.
The superior biological action of the compositions, or the sequence of applying its components, over the individual active ingredients in, for instance, grassy plants, legumes and oil plants, can be convincingly shown in experiments in the open.
The triazole compounds given below have proved to be particularly suitable. To be able to present the results more simply, the substances employed are characterized as follows in the tables below: 3 0 A 1-(2,4-dichlorophenyl)-1-methyl-2-methoxy-2-( -H-1,2,4-triazol-1-yl)ethanol Example 11 of EP-A-56 087) B 1-phenoxy-3-(1H-1,2,4-triazol-1-yl)-4-hydroxy-5,5-dimethylhexane Example a of EP-A-40 350) 1 C 1-(4-trifluoromethylphenyl)-2-(1,2,4-tCiazol-l- yl)-3-(5-methyl-1,3dioxan-5-yll-propen-3-ol Example 39 of EP-A-43 923) D -(2-ethyl-5-methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl-3- (4-methylphenyl)-propan-1-ol Example 54 of EP-A-44 407) E N,N,N-trimethyl-N-2chloroethylammonium chloride i~ 1 i BASF Aktiengesellschaft O.Z. 0050/39048 F N,N-dirnethylpiperidinium chloride G 2-chloroethylphosphonic acid H N,N,N-trimethyl-N-2-chloroethylammonium chloride and 2-chloroethylphosphonic acid in a ratio of 2:1 I N,N-dimethylpiperidinium chloride and 2-chloroethylphosphonic acid in a ratio of 2:1 J 5,.(4-chlorophenyl)-3,4,5,9,10-pentaazatetracyclo[5,4, 1 02 6,08,11]dodeca-3,9-diene.
The experiments were run on plots either 12.5 m 2 (cereals) or 25 m 2 (peas and rape) in size, with four replicates, Cultivation, fertilizatin and S the use of crop protection agents against weeds, and attack by fungi and S* injurious insects were standard for the location.
The bioregulator compositions were applied either as wet dressings or as foliar sprays, the agents in the latter instance being dispersed in 400 liters of water and applied at a pressure of 3.5 bar.
The cereal yields are based on a constant dry mass content of 86..
Examples 1 and 2 Compositions of substances A and C, applied to spring wheat from the commencement to the middle of the tillering phase, resulted in growth inhibition and an increase in yield 17') far better than the growth inhibition and increase in yield achieved with the individual components A and C, The synergistic effect may be determined in accordance with the formula devised by S.R. Colby ("Calculating synergistic and antagonistic responses of herbicide combinations"; Weeds, 15, 1967, p. 29-22) E s X Y 1 100 BASF Aktiengesel.lschaft 00$0/1904a :l BASF Aktiengesellschaft O.Z. 0050/39048 where E denotes the expected additive growth inhibition achieved by A C, X is the growth inhibition achieved by active ingredient A, and Y is the growth inhibition achieved by active ingredient C, Application of this formula to Example 1 gives the following result: E 3.7 0.7 3.7 x 0.7 4.37 cm 100 The growth inhibition is 7.5 cm, compared with the expected growth inhibition of 4.37 cm. In other words, the synergistic effect of tM,) composition is 3.13 cm. The synergistic effect of the composition can be determined in an analogous manner in the remaining examples, 1t t t t n
Y
1* BASF Aktiengesellschaft0z.05/94 O.Z. 0050/39048 Example 1 Crop: Soil type: Sown: Assessed: Spring wheat of the Schirokko variety clay 13,03.84 18 .06.84 Agent g active Treatment Growth height (difference) ingredient/ha date cm untreated 0 82,6 100 A 1000 04.05-84 78.9 96 C 125 81,9 99 C-1) A C 1000 125 75.1 91 Example 2 Crop; spring wheat of the Schirokko variety Soil type: clay Sown: 13,03.84 Assessed: 21,08484 Agent g of active Treatment Cereal yiel.d (difference) ingiredient/ha date in 100's of kuq/ha untreated 0 64.9 100 A 500 04405.64 60,0 92 C-8) C 250 59.7 92 C-8) A C 500 250 6 101 1~' BASF Aktiengesellschaft 02Z. 0050/39048 Examples 3 to The treatment of spring wheat and winter barley with compositions of substances A E from the middle to the end of tillering gave similar results, Compared with the application of the individual components, the growth inhibition achieved by the composition was from -2 to -6Z.
Example 3 Crop: Soil type: Sown; Assessed: Spring wheat of the Inia variety sandy loam 05,06.86 07 .09,186 (3M Agent g (if a, i. Treatment Growth height (difference) 4er ha date cmI untreated 0a6. 100 A 500 06,00, 86 72o3 84 (-16) E 690 "86.2 C- 0.0) 100 A E 500 690 68.8 80 Example 4 Crop: Winter barley of the Ger'bel variety Soil type: clay Sown: 23,09,83 Assessedt 24,05,84 Agent g of a, i. Treatment Growth height (di-fference) pgr ha date c. m untreated 0 -107,1 100 A 500 17.04.04 106.7 99 E460 0,106.3 (fth,0) 99 (-I1) A E 500 460 of 103.5 96 BASF Aktiengesellschaft0Z. 05/04 O.Z. 0050/39048 Example Crop:, Soil type: sown: Assessed: Winter barley of the Igri variety loamy sand 27,09,84 20, 05,85 Agent g of ai Treatment Growth height (difference) per ha Date cmI untreated 0-84,1 100 A 750 09 .04 ,85 75.5 8.6) 90 E 1380 84,.8 0.7) 101 1) A E 750 +t38Q 71,4 85 215 Examples 6 and 7 Fairly short stems are moee rststant to lodging, When a composition of A E was appited to winter barley from the middle to the end of tillering, the resistance to lodging was improved by +17 4 compared with the individual components, This improviO resistance to lodging' al!)o resultPOd in, an increase in yield of 11 650 kg/ha, Example 6 Crop,, PO Soil, type: Sown: Assessed; Winter barley of the Igri variety loamy sand ZOM.984 24405,85 Agent 9 of a i. Treatment Lodgi.ng (Difference) ver ha Wae 7, untreated
A
E
A+ E 0 750 1:300 750 0300 t8 04.8 V 5 50 2) 36 (-Z4) BASF Aktiengesellschaft Exam~ple 7 Crop: Winter banl Soil type: loamy sand Sown: 28.09.84 Assessed: 17.07.85 Agent g of a'i per ha untreated 0 A 750 lit E 1380 A E 750 +1: Example 8 0.Z. 0050/39048 q Y of the 1gri variety Treatment Cereal yield (difference) Date in 100's of k0/ha I 380 18.04 .85 58. 8 66, 4 7 .6) 56,3 2,5) 70.4 (+11.6) 100 113 (+13) 96 4) 120 In winter rye (Secale cereale too, the application of a composition of A E achieved a growth inhibition superior to the sum of the individual actions (-20 The compounds were applied here as seed dressings.
Example 8 44 4.4k 41 4 crop:" Soil type: Sown;* Assessed: Winter rye of the the Danko variety loamy sand 30.09.83 25, 10.83 I I I 4 30
I
1*44 44 4 4 44 1 44 Agent (~of a~i, Treatment Growth height (difference) ver ha Date cmh untreated 0 -10.0 100 A 10 29,09.83 910 90 E 250 48,0 V2.0) 80 A .E 10 250 5,0 V510) s0 /;1 r i i 1
I
ii. ii-ii;i-i:j;l i-~i lir BASF Aktiengesellschaft 0.Z. 0050/39048 Examples 9 to 11 Not only compounds A E applied Ps a composition, but also as a sequence of individual applications gives a surprising synergistic action. With reference to oats (Avena sativa), the application for example of substpnce A during the development stage extending from the first node to the appearance of the last leaf, and of substance E during the development stage extending from the appearance of the last leaf to the commencement of ear protrusion resulted in a growth inhibition and a corresponding improvement in resistance to lodging (+41Z) and in yield it I I I I Ir f i9 I t it tc t ti I i I I Example 9 Crop: Soil type: Sown: Assessed: Oats of the Flimingskrone variety loamy sand 12,03.85 27.06.85 Agent g of a.i, Treatment Growth height (difference) per ha date cm untreated 0 122.2 100 A 750 24.05.85 118.0 4.2) 96 4) E 1380 30,05.85 109,9 90 A 750 24.05.85 E +1380 30.05.95 101.8 83 (-17) -7 BASF AktiengesellschaftO..00/94 O.Z. 0050/39048 Example Crop: Soil type: Assessed: Oats oF the Panther variety heavy loamy sand 20. 03 01 .08.85 ist I t 'r Agent g of a.i, Treatment Lodging (difference) per ha ljate untreated 0 93 A 750 04. 06. 85 84 E 1380 07,06.85 70 (-23) A 750 04.06.85 E +1380 07.06.85 20 (-73) I~t2O) Example 11 Crop.
Soil type: Sown:, 2,j Assessed: Oats of the Flfimingskrone variety loamy sand 12.C3.85 07.08,85 Agent g of a.i. Treatment Cereal yield (diffrence) per ha date in 100's of ku/ha 7~ untreated 0 69.3 100 A 750 24 .05.85 60,0 C-1.3) 98 1380 30.05,85 70,0 101 A 750 24.05,85 E +13130 30.05.85 71,3 2.0) 103 I BASF Aktiengesellschaft o.z. 0050/39048 Examples 12 to 14 When substance A was mixed and applied with substance G, a synergistic effect was again observed. This is recognizable from experiments with winter barley. Treatment was effected when the ligule of the last leaf was visible up to commmencement of ear protrusion. The composition had the following effects compared with the application of the individual components: 3% growth inhibition, 5% increase in yield, and an increase in thousand kernel weight of 7% g) as an indication of quality.
Example 12 Crop: Soil type: Sown: Assessed: Winter barley sandy loam 25.09.84 31,05.85 of the Tapir variety Agent g of a.i, Treatment Growth height (difference) per ha date cm. untreated 0 130.2 100 A 750 17,05,85 12\,0 1.2) 99 1) G 480 115.9 89 (-11) A G 750 +1380 110.4 85 Example 13 Crop: Winter barley of the Tapir variety Soil type: clayey loam Sown: 28.09.84 Assessed: 15,07.85 Agent g of a.i. Treatment Cereal yield (difference) per ha date in 100's of kg/ha untreated 0 62.1 100 A 750 07,05.85 66.7 4.6) 107 7) G 480 61.1 1.0) 98 2) A G 750 480 68.6 6.5) 110 I I BASF Aktiengesellsch.
Example 14 Crop: Winter ba Soil type: sandy loa Sown: 25.09.84 Assessed: 21.08,85 Agent g of per 0 untreated 0 aft O.Z. 0050/39048 arley of the Tapir variety >m a.i.
ia Treatment date 1,000 kernel weight (difference) "15 SIt s A 750 G 480 A G 750 41,6 100 17,05.85 42.6 1.0) 102 2) 41.5 0.1) 100 480 45.2 3.6) 109 9) Examples 15 to 18 Sequential application of substances A and H also had synergistic effects, confirming the results obtained in Examples 9 and 10. Substance A was applied during the period extending from the middle of tillering to the S 25 time when the first noce in winter barley could be felt. The same plants were treated with substance H in the period from the appearance of the last leaf up to protrusion of the ear tips. Compared with single applications of the individual components, this sequential application resulted in synergistic effects of 3 X growth inhibition, 23 to 25 1 improved 31 resistance to lodging, and a 2 increase in yield (+150 kg/ha), i i i BASF Aktiengesellschaft0.. 05104 O.Z. 0050/39048 Example Crop Soil type: Sown: Assessed: Winter barley of' the Igri variety loam 28. 09.84 05. 06 C 9 C9 II 4 ft. 9 ft ft 4 f Agent g of a.i. Treatment Growth height (difference) per ha date cmI untreated 0 106.2 100 A 750 18,04.85 94.0 88 (-12) H 690 09.05.85 102 .7 3.5) 97 3) A 750 18.04.85 H 690 09.05.85 86.7 82 (-18) E~xample 16 Crop: Soil type: Sown: Assessed: Winter barley of the Viola variety heavy, sandy loam 25 .09 .84 13.06.85 Agent g of Treatment Lodging (difference) per ha date untreated 0 100 A 750 04,04.85 83 (-17) H 690 13.05.85 100 0) A 750 04.04,85 58 (-42) H .'690 13.05.85 BASF Aktiengesellschaft 0.Z. 0050/39048 Example 17 Crop: Soil type: Sown: Assessed; Winter barley of the Franka variaty heavy, sandy loam 3 0 09 .8 4 15.07.85 i It t
I
I t I Agent q of Treatment Lodging (difference) per ha date untreated 0 100 A 750 17,04.85 58 (-42) H 690 30.05.85 88 (-12) A 750 17.04.85 23 V77) H 690 20.05.85 Example 18 Crop: Soil type: Sown: Assessed: Winter barley of the Igri variety loam 28.09.84 17,07.85 Agent g of a4.. Treatment Cereal yield (difference) per ha date in 100's of kci/ha 7/ untreated 0 67.6 100 A 750 18.04.85 74 .2 6.6) 110 H 690 W905185 70.6 3.0) 104 4) A 750 18,04.85 78,7 116 (+16) +H 690 09,05,85 1; BASF Aktiengesellschaft 19 O.Z. 0050/39048 Example 19 The sequential treatment of winter barley plants with substances A I also resulted in a corresponding synergistic action. In this case, substance A was applied in the period from the end of tillering to shoot commencement, and substance I was applied to the same plants at the beginning of ear protrusion. Compared with single applications of the Sindividual components, this sequential treatment resulted in an improve- J ment in resistance to lodging of 31 Example 19 Crop: Winter barley of the Illia variety Soil type: clayey loam S' 15 Sown: 11,10.84 S Assessed: 27.06.85 if j 1 Agent g of a.i, Treatment Lodging (difference) per ha date untreated 0 38 A 750 13.04.85 21 17) I 1150 21.05.85 65 27) 25 A 750 13.04,85 17 21) I +1150 21.05.85 Examples 20 to 22 Similarly to the composition of subltances A E (Exalple 8) the use of a composition of A 3 as a seed dressing in spring wheat and winter rye had synergistic effects: the resistance to lodging was increased by 20 to 36 and the corn yield by 8 (+510 kg/ha).
"A
VI
BASF Aktiengesellschaft O.Z. 0050/39048 Example Crop: Soil type: Sown: Assessed: Spring wheat of the Kolibri variety clay 16. 03 84 26. 06. 84 Agent g of Treatment Lodging (difference) per ha date7 untreated 0 A 2,5 15.03.84 78 28) G 2.5 13 C-37) A G 2.5 2,5 5 Example 21 Crop: Soil type; Sown: Assessed: Spring wheat of the Kolibri, variety Ci lay 1 6 .03 21 .08, 84 Agent g of Treatment Cereal yield (difference) oer ha date in 100's of kc/ha untreated 0 63,51 A 2.5 15.03.a4 61.2(- 2.3) 96 C-4) 3 2.5 62.7(- 0.8) 99 C-1) A J 2.5 2.5 65.5(+ 2.0) 103 3) :7 I BASF Aktiengesellschaft O.Z. 0050/39048 Example 22 Crop: Soil type: Sown: Assessed: Winter rye of the Danko variety loamy sand 30,09.83 10.07,84 Agent g of ai. Treatment Lodging (difference) per ,ha date_ untreated 0 A 10 29,09.83 30 3 5 50 A J 10 5 0 That the ahovementioned synergistic actions of compositions or combinations with triazoles and other bioregulatory substances are not restricted to a certain triazole is illustrated by the following examples.
Examples 23 to 26 Leaf treatment of winter and spring wheat, and of winter rape (Brassica napus with a composition of substances B E resulted in a synergistic inhibition of growth compared with the individual components, On leaf application to winter wheat during tillering, this inhibition amounted to 4 to and 6s in the case of spring wheat. When rape was treated during shoot formation, growth inhibition amounted to 137.
I r BASF Aktiengesellschaft0..05/04 O.Z. 0050/39048 Example 23 Crop: Soil type: Assessed: Winter wheat of the Kronjuwel variety sandy loam 17. 10.85 22.05.86 Agent g of a.i, Treatment Growth height (difference) per ha date cm untreated 0 -67,0 100 B 450 23,04,86 66-0 C-1.0) 98 C-2) E 345 F12.0 92 C-8) B E 450 345 '57,0 85 Example 24 Crop-, Winter wheat of the Kanzler variety Soil type; loamy sand Sown: 28,10.85 Assessed,- 22.05.86 Agent g of a,i. Treatment Growth height (difference) per ha date cm untreated 0 70.0 100 B 450 25,04,86 67.3 96 4) E 690 61 .8 8.2) 88 (-1IM a C 450 690 56.0 80 BASF Aktiengesellschaftoz.a0/o4 OZ. OUrIO/39048 Example Crop: Spring wheat of the Inia variety Soil type: sandy loam 05.06.86 Assessed: 10,09.86 Agent g of aj,. Treatment Growth height (difference) per ha date cmI untreated 0 89,0 100 B 500 06,08,86 80.0 9.0) 90 E 460 78,6 88 B E 500 460 64 ,0 72 (-28) Example 26 Crop: Wi~nter rape of the Elena variety S6111 typet loess Sown; 27,08.85 Assessed: 06.05.86 Agent g of ail Treatment Growth height (dif ference) per ha date cm I/ untreated Q0 10 z .0 100 B 450 17,.04 ,86 59.6 58 E 1380 102.0 0) 100 B, E 450 250 '46,1 45 egamplas 27 to ,X2 Compositions of' substances 0 E also, resulte.' in~ a synergistic action compared tolth their individual componenits. Wh ,n spring and winter wheat was treated during tiltering, the synergistic growth inhibition was found to be, from 5 to 124,. and in the case rf spring wheat from 9 to 121., BASF Aktiengesellschaft Example 27 Crop; Spring whea~ Soil type: sandy loam Sown: 04.06,86 Assessed; 08,09,86 0,Z, Out0I39048 t of the Inia variety Agent g of a, i, Treatment Growth height (difference) per ha date cmI untreated 0 8612 100 O 250 07.0086 76,4 89 (-11) E 690 8 5 .2 1- 1.0) 99 I1) 0 E 250 +1380 It67.9 79 (-21) Example 28 Crop: Spring wheat of the Inia variety Soil type: sandy loam Sown;, 05.06,86 Assessed; 10,09,86 Agent g Of atif Treatment Growth height (differ'ence) -per ha date cmY untreated 0 89,0 100 o 500 06,08,86 71,6 17,4) 80 E 460 78,6 48 (-12) O E 500 460 5Q,O 56 (-44)
I
0 9 0 354 BASF Aktiengesel~lschaft? Example 29 Crop: Winter wheat of the~ -o4 var iety Soil type; clay Sown; 17,10,85 Assessed; 22,05,GG 0 ,Z 0 t,5 a/19 04 8 Agent g of a,1, Treatment Growth height (difference) Der ha date cmI untreated 0 6.8 100 0 500 25,04.86 64,.2 84 -16) E 460 7 2 6,3) 91 9) D E 500 460 5 Q .0 65 Example Crop Winter wheat of the Kanzler variety Soil type: sandy loam Sown-, 16.10,5 Assessed: 22,605,86 Agent g Of a~i, Treatment Growth height (difference) p_ er ha dte cm 'I untreated 0 54,8 100 D 500 25.04,86 45 .0 9. 98) 82 (-18) E 690 50.0 (4 4,8) 91 C-9) 0 E 500 +690 3 7 ,5 68(-2 "1111,11, -1 1 "I ii Pwiw-, BASF Aktiengesellschaft 26 Example 31 Crop: Winter wheat of the Dolomit variety Soil type; sandy loam 1?10.85 Assessed: 22.05.86 02Z, 0050/39048 Agent g of a'i, Trea tment Hn Growth height (difference) untreated 0 -74 ,2 100 D 750 23,04,8G 62.5 84 (-16) E 460 '69,8 4.4) 94 6) D E 750 460 54.2 73 (-27) Example 32 crop: Winter wheat of the Dolomit var~iety Soil type: sandy loam Sown, 17,100,85 Assessed: Z22.05.86 Agent 9 Of acii Treatment Growth height (difference) oer ha date cm YA untreated 0 -74.2 100 D 750 23.04.86 62,5 84 (-16) E 690 705 3.7) 95 D E 7 .0 690 49,8 67 (-33) __d BASF Aktiengesellschaft o.z. 0050/39048 Example 33 Synergistic effects of compositions of triazoles and other bioregulators were observed pt .,ly on grassy and oilseed plants, but also in legumes.
For example, leaf treatment during the budding stagea in peas (Pisym sativum with a composition of D H resulted in a synergistic inhibition of growth, compared with the individual components D and H, of 10 X.
Example 33 Crop: Soil type; Sown: Assessed: Peas of the Stehgold variety sandy loam 07.04,86 18.06,86 t
I'
1 r z t r Agent Active ingr. Treatment Growth height (difference) q/ha date cm untreated 0 58,0 100 D 500 21,04,86 54,5 3,5) 94 6) h 1380 55,7 2,3) 96 4) D H 500 1380 46.4 80 25 Example 34 The synergistic action of the compositions according to the invention in cotton, spring and winter rape is demonstrated in Examples 34 to 39, 3O Crop: Soil type: Sown: Assessed: Cotton of the IAC-20 variety sandy loam 05,11.86 15,.04.87 Agent Active ir'.r, Treatment Yield (difference) n/ha date kg/ha 7 untreated 0 1340 100 8 500 14.01.87 1420(+ 80) 106 6) F 50 1420(+ 80) 106 6) B F 500 50 1621(+281) 121 (21) BASE Aktiengesellschaft0Z. 00/ 04 OZ. 0050/39048 Example Crop: Soil type: Sown: Assessed: Spring rape of the Callypso variety sandy loam 10 U13 3 7 Lodging; 20,08.87 Yield: 30.09.87
'I
itt Ai Agent Active ingr. Treatment Lodged area Yield g/ha date (difference) (difference) 7 100 kq/ha 7 untreated 0 100 15.2 100 B 300 30,06.87 100 20,7 136 (+36) 1 920 100 15,8 104 4) B 1 300 9 ?O 0 (-100) 21,7 143 (+43) Example 36 Crop; Spring rape of the Westor variety Soil type: sandy loam Sown: 09.06.87 Assessed; Growth height: 27,07.'W? Lodging: 06,88 Agent Active ingr, Treatment Growth ht (difference)Lodging (cliff,) aq/ha date -cm 7 untreated 0 -101.7 100 47 B 125 14 .07 .87 103.3(+1.6) 94 H6) 28 (-19) E 460 10 1 7 0) 96 C-4) 30 (.17) B E 125 460 80 8 I1 I j BASF Aktiengesellschaft 0.Z. 0050/39048 Example 37 Crop: Soil type: Sown: Assessed: Spring rape of the Callypso variety sandy loam 12.03 .87 Lodging; 27.07,87 Yield: 30.09.87 Agent Active ingr, Treatment Lodged area (diff.) n/ha date Yield (difference) 100 kq/ha 'I it II II t I tt *15 I,.i t
C
9* CC C C 9 C C 4
CC
4 *9 4.
9S C
CC
untreated 0 100 16.0 100 B 300 19,06.87 75 V.25) 19.8 124 (+24) E 920 100 16.3 102 2) B E 300 920 0 (-100) 21,4 134 14) Example 38 Crop: Winter rape of the Jupiter variety Soil type; sandy loam Sown; 26,08,86 Assessed: Growth ht: 24.05 .87 Lodging: 21.08.87 Agent Active ingr. Treatment Growth ht, (difference)Lodging (diff) n/lha date cm 7 tendency I untreated 0 106,0 100 72 8 450 05,05.87 97o5(- 8.5) 92 C-8) 48 (-24) E 1380 '104.7(- 1,1) 99 C-1) 62 8 E 450 1380 88.0(-18,0) 89 20 (-52) IL Ci I C C
I
r BASF Aktiengesellschaft Example 39 Crop: Winter rape Soil type: sandy loam 14.08.87 Assessed: Growth ht: Lodging ten Yield O.Z. 0050/39048 of the dency: Lirabin variety 20 .05 .87 04 .08. 87 20 .08, 87
ID
Agent Active ing. Treatment Growth ht. Lodging tendency Yield g/ha date (difference) (difference) (difference) cm 7 100 kn/ha untreated 0 138.4 100 70 32,4 100 8 455 08. 05 .87 133.2(-3,2) 98 45(-25) 39.1(+6,7)120(+20) H 1380 135.1(-113) 99 74(+ 4) 36.7(4.3) 113(+13) 8 H 450+ 1380 119 .4 17 88(-12) 18(-52) 51.1(18,7)157(+57) C C te t 4 4~
I
II
4 4
Claims (4)
1.An agent for regulating plant development, containing a synergistic composition of a growth-regulatory triazole compound of the formula Ia. 1b, Ic or Id OH CH2) Y R Ia OH lb 9~ N4 C93 OH A'-.O-(CH
2 N N Id A denoting unsubstituted phenyl or phienyl substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or CF 3 and R denoting tert.-butyl or the group CH 3 where R 2 is hydiogen, methyl or ethyl, and n is an integer from 2 to '4 t BASF Aktiengesellschaft 0.Z. 0050/39048 and either a qunternary thianium or ammonium salt selected from the group consisting of NN-dimethylazacycloheptanium salts, NN-dimethylpiperidinium salts, N,N-dimethylhe~ahydropyridazinium salts N ,N-dimethyltetrahydropyridazin i salts, N-methylpyridium salts, N,N-dimethylpyrrolidium saltsAand NIN-trimethyl-N-2- chloroethylammonium salt, and/or a phosp .onic acid compound selected from the group consisting of 2- chloroe thylpho sphonic acid, 2 -chlo roe thylaminoe thylpho sphonic acid, 2-chloroethylaminobutyl- pho~phonic acid, 2-chloroethylphosphonic acid-N,N-dimethylamide, 2 -chloro e tIylphos phonic acid-N-methYlamide, vinyiphosphonic acid, propylphosphonic acid, phosphonomethylglycineA and benzyl osponic acid, and/or the compound 5- 4-chlorophenyl) 3.4,5, 9, 10-pentaaza tetra- cycloF 5 ,4 02. 6, 08. 11 3dodeca-3 ,9-diene, a 0~ 0 15 2. .9 q 9 9, 9, 0 A process for regulating plant development, wherein the soil, the seed and/or the plants are treated with a synergistic composition as set forth in claim 1
3, A process as set forth in claim 2, wherein the soil., the seed and/or the plants are treated with from 0.1 to 95wtX of a synergistic com- position as set forth in claim 1 in addition to conventional carriers,
4, An agent as set forth in claim I I containing a synergistic composition of a triazole compound la, lb. Ic or Id and N,N-dimethylpiperidinium chloridL, 2- chloroethylpho sphonic acid or 5-(4-chlorophenyl)- 3,4, 5 10 0-pentaaza tetra cyclo C 5,4 ,02,6,08 1.1 )dodeca-3 ,9-diene. An agent as set forth in claim 1 containing a synergistic composition of a triazole compound I b, Ic or Id and N,N-dimethylpiperidinium chloride or N,N,N-trimeth, l-N-2-chloroethylammonium chloride, each in admixture with 2-chloroethylphosphonic acid, I DATED this 23rd day of March 1988. BASF AKTIENGESELLSCHAFT EDWD. WATERS SONS PATENT ATTORNEYS QUEEN STREET MELBOURNE. VIC. 3000. I ~j
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19873709806 DE3709806A1 (en) | 1987-03-25 | 1987-03-25 | AGENTS FOR REGULATING PLANT GROWTH |
| DE3709806 | 1987-03-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU1355188A AU1355188A (en) | 1988-09-29 |
| AU592494B2 true AU592494B2 (en) | 1990-01-11 |
Family
ID=6323944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU13551/88A Ceased AU592494B2 (en) | 1987-03-25 | 1988-03-24 | Agents for regulating plant growth |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0285880A3 (en) |
| JP (1) | JPS63255206A (en) |
| CN (1) | CN1030171A (en) |
| AU (1) | AU592494B2 (en) |
| BR (1) | BR8801350A (en) |
| CS (2) | CS276127B6 (en) |
| DD (1) | DD268145A5 (en) |
| DE (1) | DE3709806A1 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4300452A1 (en) * | 1993-01-11 | 1994-07-14 | Bayer Ag | Plant growth inhibitor |
| NZ260462A (en) * | 1994-05-05 | 1996-04-26 | Horticulture & Food Res Inst | Tree treatment and composition comprising phosphorous acid, a bioprecursor or a salt thereof and a triazole |
| CA2443401C (en) | 2001-04-12 | 2011-10-25 | Basf Aktiengesellschaft | Bioregulatory combination of active agents |
| JP2013056832A (en) * | 2010-01-12 | 2013-03-28 | Univ Of Tokyo | Strigolactone biosynthesis inhibitor |
| WO2011110583A2 (en) * | 2010-03-10 | 2011-09-15 | Basf Se | Fungicidal mixtures comprising triazole derivatives |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0043923A2 (en) * | 1980-07-10 | 1982-01-20 | BASF Aktiengesellschaft | 1,3-Dioxan-5-yl-alkenyl triazoles, their preparation and their use as plant growth regulators |
| EP0044407A2 (en) * | 1980-07-09 | 1982-01-27 | BASF Aktiengesellschaft | 1,3-Dioxan-5-yl-alkyl triazoles, their preparation and their use as plant growth regulators |
| EP0056087A1 (en) * | 1980-12-18 | 1982-07-21 | BASF Aktiengesellschaft | Use of alpha-azolylglycoles as plant growth regulators |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2361410A1 (en) * | 1973-12-10 | 1975-06-19 | Basf Ag | GROWTH REGULATORY AGENTS |
| DE2755940C2 (en) * | 1977-12-15 | 1986-01-02 | Basf Ag, 6700 Ludwigshafen | Means for regulating plant growth |
| DE3019049A1 (en) * | 1980-05-19 | 1981-12-03 | Basf Ag, 6700 Ludwigshafen | NEW AZOLES |
| GB2081700B (en) * | 1980-07-28 | 1984-06-27 | Ici Ltd | Method of regulating plant growth |
| DE3102588A1 (en) * | 1981-01-27 | 1982-08-12 | Bayer Ag, 5090 Leverkusen | AGENTS FOR INHIBITING PLANT GROWTH |
| JPS59204105A (en) * | 1983-05-02 | 1984-11-19 | Sumitomo Chem Co Ltd | Plant growth regulation composition |
| DE3524334A1 (en) * | 1984-07-10 | 1986-01-23 | Basf Ag, 6700 Ludwigshafen | Plant growth regulators |
-
1987
- 1987-03-25 DE DE19873709806 patent/DE3709806A1/en not_active Withdrawn
-
1988
- 1988-03-18 EP EP19880104320 patent/EP0285880A3/en not_active Withdrawn
- 1988-03-21 CS CS183888A patent/CS276127B6/en unknown
- 1988-03-21 CS CS204190A patent/CS276154B6/en unknown
- 1988-03-23 DD DD31392588A patent/DD268145A5/en not_active IP Right Cessation
- 1988-03-24 BR BR8801350A patent/BR8801350A/en unknown
- 1988-03-24 AU AU13551/88A patent/AU592494B2/en not_active Ceased
- 1988-03-25 JP JP6993588A patent/JPS63255206A/en active Pending
- 1988-03-25 CN CN 88101649 patent/CN1030171A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0044407A2 (en) * | 1980-07-09 | 1982-01-27 | BASF Aktiengesellschaft | 1,3-Dioxan-5-yl-alkyl triazoles, their preparation and their use as plant growth regulators |
| EP0043923A2 (en) * | 1980-07-10 | 1982-01-20 | BASF Aktiengesellschaft | 1,3-Dioxan-5-yl-alkenyl triazoles, their preparation and their use as plant growth regulators |
| EP0056087A1 (en) * | 1980-12-18 | 1982-07-21 | BASF Aktiengesellschaft | Use of alpha-azolylglycoles as plant growth regulators |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1030171A (en) | 1989-01-11 |
| JPS63255206A (en) | 1988-10-21 |
| CS8801838A2 (en) | 1991-07-16 |
| DE3709806A1 (en) | 1988-10-06 |
| CS276154B6 (en) | 1992-04-15 |
| BR8801350A (en) | 1988-11-01 |
| CS276127B6 (en) | 1992-04-15 |
| EP0285880A3 (en) | 1991-01-02 |
| AU1355188A (en) | 1988-09-29 |
| EP0285880A2 (en) | 1988-10-12 |
| DD268145A5 (en) | 1989-05-24 |
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