CA2048275A1 - Synergistic agents for regulating plant growth - Google Patents
Synergistic agents for regulating plant growthInfo
- Publication number
- CA2048275A1 CA2048275A1 CA002048275A CA2048275A CA2048275A1 CA 2048275 A1 CA2048275 A1 CA 2048275A1 CA 002048275 A CA002048275 A CA 002048275A CA 2048275 A CA2048275 A CA 2048275A CA 2048275 A1 CA2048275 A1 CA 2048275A1
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- Prior art keywords
- alkyl
- alkoxy
- salts
- methyl
- plant growth
- Prior art date
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Classifications
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
- A01N25/10—Macromolecular compounds
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- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cultivation Of Plants (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
O.Z. 0050/41834 Abstract of the Disclosure: Plant growth regulators contain a synergistic mixture of one or more growth-regulating quaternary anunonium salts and an imidazolinyl derivative of the general formula II
II
where R1 is alkyl, R2 is alkyl or cycloalkyl, R3 is hydrogen, hydroxyl, alkyl, alkoxy, alkylamino, dialkylamino or unsubstituted or substitutd phenyl, phenoxy or phenylamino, R4 is hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio or haloalkylthio and R5 and R6 independently of one another are each one of the groups stated for R4 or together form an unsubstituted or substituted 1, 3-butadiene-1,4-diyl group, and inert additives.
II
where R1 is alkyl, R2 is alkyl or cycloalkyl, R3 is hydrogen, hydroxyl, alkyl, alkoxy, alkylamino, dialkylamino or unsubstituted or substitutd phenyl, phenoxy or phenylamino, R4 is hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio or haloalkylthio and R5 and R6 independently of one another are each one of the groups stated for R4 or together form an unsubstituted or substituted 1, 3-butadiene-1,4-diyl group, and inert additives.
Description
7 ~
O.Z. 0050/41834 Synerqistic aqents for requla~in~ ~lant qrowth The present invention relates to agent~ for regulating plant growth, containing a synergistic mixture of one or more growth-ragulating qua~ernaxy ammonium salts from the group consis~ing o~ the compounds I, comprising N,N-dLmethylazacycloheptani~m salt~, N,N
dimethylpipexidinium salts, N,N~dimethyltetrahydro-pyridazinium salts, N,N,N-trimethyl-N-~-chloroethyl-ammonium salts~ N-methylpyridinium salts and N,N-dLme-thylpyrrolidinium salts, and an imiclazolinyl derivativeof ~he ~eneral formula II
R 5~COR 3 I I
R 6 N~R 1 HN O
wh~re R1 i~ Cl-C4-alkyl, R2 i~ Cl-C4-alkyl or C3-C~ CYC1G_ alkyl, R3 iS ~ydrogen, hydro~yl, Cl-Cl2-alkyl, Cl-Cl2-alkoxy, C1-C1~-alkylamino, di-Cl-Cl2-alXylamino or is phenyl t phenoxy or ph~nylamino, where the aromatic radicals may carry from one ~o five halogen atoms and/vr from one to three of the following group~: Cl-C4-alkyl ~
Cl-C4-haloalkyl, Cl-C4-alkoxy, C~-C4-haloalko~r, C~ 4-alXylthio or C1-C4-haloalkylthio, R4 is hydrogen, halogen?
Cl-C4-alkyl, Cl-C4-haloallcyl, Cl-C,,-alkoxy, Cl-C4-haloalkoxy, Cl~C4-alkylthio or C1-C4-haloalkylthio and ~5 and R~ lndepend~ntly of one another are each one of the group~ ~tated for R4 or together form a 1,3-butadiene-1,4-diyl group which may carry from one to four halogen atomsand/or from one to three of the following groups: C1-C4-alkyl r C1-C4-haloalkyl, Cl-C4-alkoxy, Cl~C4 haloalko:~y, Cl-C4-alkylthio or Cl-C4-haloal~ylthio, and inert additives.
The present invention furthermore relates to methods ~or regulating plant growth with these agents.
~ uaternary ammonium compound~ are disclosed in the literature as plant growth regulators (DE-A 22 07 575). The li~erature alco describes 'j ,~ ~" ~
- Z - O.Z. 0050~41834 imidazole deriYatives as herbicides ~DE-A 31 21 736).
Mixtures of N,N,N-trimethyl-N ~-chloreethylammonium s~lts and 2-(4-isopropyl-4-methyl-5-oxo-2-Lmidazolin-2-yl)-3-quinolinecarboxylic acid having growth-regulat.ing properties are ~lso known (EP-A 149 083~.
I~ is an ob~ect of the present in~ention to provide novel effective ~ynergistic mixtures for regula~-ing plant growth.
~e have found that this ob~ect is achieved by ~he synergistic mixtures defined at the outset. Method~ ~or u~ing these mixtures as plant growth regulators were also found.
In view of the intended use in the novel syner-~istic growth-regulating agents, suitable substituents of the c~mpound~ II are the following radicals~
R1 is Cl-C4-alkyl, such as methyl, ethyl, propyl, 1-methyleth~l, butyl/ l-methylpropyl, 2-methylpropyl or dimethylethyl, preferably methyl, ethyl or 1-methyl ethyl, in particular methyl or l-methylethyl;
R~ is Cl-C4-alkyl, such as me~hyl, ethyl, propyl, 1-methylethyl, butyl, l-methylpropyl, ~-methylpropyl o~
1/l-~imethylethyl, preferably methyl or ethyl, in par-ticular meth~1, or C3-C6-cycloal~yl, ~uch a~ cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, preferably cyclopropyl or cyclopentyl, in particular cyclopropyl;
: R3 iY hydrogen;
C1-C12-alkyl, prefsrably branched or straight-chain Cl-C6-alkyl, such as methyl, ethyl, pxopyl, l-methyllethyl, 3~ butyl, l-mathylpropyl, 2-methylpropyl, 1,1-dLmethyllethyl, pentyl., 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2 dimethylpropyl, l-ethylpropyl~ hexyl, 1,1-dimethylpropyl, 1,2-di~ethylpropyl, 1-m~thylpentyl, 2-mekhylpentyl, 3-methylpentyl, 4~methylpentyl, 1,1-dimethylbutyl, 1,2-dlmethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-d:Lmethylbutyl~ 3,3-dimethylbutyl, l-ethylbu~yl, 2-e~hyl-butyl, l,1,2-trimethylpropyl, 1,2,2-trimekhylpropyl, - 3 - O.~. 0050~41834 1-e~hyl-1-methylpropyl and l~ethyl-2-methylpropyl, in particular br~nched or straight-chain Cl-C4-alkyl, such as methyl, ethyl, propyl, l-methylethyl, butyl, l-methyl propyl, 2-methylpropyl or 1,l~dLmethylethyl;
C~-C12-alkoxy, preferably branched or straight chain C~-C6-alkoxy, such as methoxy, ethoxyl propoxy, 1-methyl-ethoxy; butoxy, l-methylpropoxy, 2-me~hylpropoxy, 1,1-dLmethylethoxy, pentyloxy, 1-methylbutoxy, 2-methyl~
butoxy~ 3-methylbutoxy, 2,2-dLmethylpropoxy, 1-ethylprop-oxy, he~yloxy, l,l-dLmethylpropoxy, 1.,2-dLmethylpropoxy, l-me~hylpentyloxy, 2-methylpentylo~y/ 3-mathylpentyloxy, 4~Nethylpentyloxy, 1,l-dimethylbutoxy, 1~2-dimethyl-butoxy, 1~3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbuto~y, 2-lS ethylbuto~y, 1,1,2-trimethylpropo~y, 1,2,2-trimethyl-propo~y, l-ethyl-1-met~ylpropoxy or 1-ethyl-2-methyl-propoxy/ in particular branched or straight-chain Cl-C4-alkoxy, such as methoxy, etho~y, propoxy, l-methylethoxy, : ~uto~y, l-me~hylpropoxy, ~-methylpropo~y or 1,1-dLmethyl-ethoxy;
Cl-Cl2-alkylamino, in particular C1-C6-alkylamino, such as methylamino, ethylamino, propylamino, l-methylethylamino, butylamino, 1-methylpropy~lamino, 2-methylpropylamino, 1,~ dimethyle~hylamino, pentylamino, 1 methylbutylamino, 2-methylbutylamino~3-methylbutylamino,2,2-dLmethylprop-ylamino, l~ethylpropylamino, hexy~lamino, 1,1-d~nethyl-propylamino, 1,2-dimethylpropyl2mino, l-methylp~antyl-amino, 2-m~thylp~antylamino, 3-methylpentylamino, 4-methylpen~ylhmino, ~ dimethylbutylamino, 1,2-dlm~athyl-butylamino, 1,3-dimethylbutylamino, 2,2-dimethylbutyl-amino, 2,3-dimethyl~u~ylamino, 3,3-dimeth~lbutylamino, 1-ethylbutylamino~ 2 ethylbutylamino; 1,1,2-trimethylprop-yl~nino, 1,2,~-trimethylpropylamino, 1 ethyl-l-methyl-~,, propylamino and 1-ethyl-2-methylpropylamino;
di-C1-C12-alkylamino, in particular di-C~-C~-alkylamino, preferably di-Cl-Cb-alkylamino, ~uch a~ N,N~dimethyl~mino, diethylamino, N,~-dipropyl~mino, ~,N-di-(1-methyl-., ;~
, ., ,, .
- ~ - O.Z. 0050/41~34 ethyl)amino, N,N-dibu~ylamino, N,N-di~(1 methylpropyl)~
amino, N,N-di-~2-methylpropyl)-amino, N,N-di-(1,1-dLmethylethyl)-amino, N-ethyl-N-methylamino, N-methyl-N
propylamino, N-methyl-N-(l-methylethyl)-amino, N-butyl-N-methylamino, N-methyl-N~ methylpropyl)-amino, N-methyl-N-(2-methylpropyl)-amino, N-(1,1-d~nethylethyl)-N-methylamino, N-ethyl-N-propylamino, N-ethyl-N-(l-methylethyl)~amino, N-butyl-N~ethylamino, N-ethyl-N-(l-methylpropyl)-amino,N ethyl-N-(2-methylpropyl)-amino,N-ethyl-N~ d~nethylethyl)-~mino, N~ methylethyl)-N-propylamino, N-butyl N-propylamino, N-(1-methylpropyl)-N propylamino, N~(2-methylpropyl)- N-propylamino,:N-(l,l-dLmethylethyl)-~-propylamino, N-butyl-N-tl-methylethyl) amino, N~ methylethyl)-N-(1-methylpropyl)-amino, N~
methylethyl)-N (2-methylpropyl)-aminol N-(1,l-dLmethyl-ethyl)-N-Il-methylethyl) amino, N-butyl-N~ methyl-propyl)-amino,N-butyl-N~(2-methylpropyl)-amino,N-butyl-N-(l,l-dimethylethyl)-amino, N~ methylpropyl)-N-(2-methylpropyl)-amino, N-(l,l-dLmethylethyl)-N (1 methyl-propyl)-amine and N-(l,l-dLmethylethyl)-N~(2-methyL-propyl)-amino;
phenyl, phe~o~y or phenylamino, where the aromatic radical3 may carry from one to five halogen atoms, such a~ fluorine, chlorine, bromine or iodine, preferably fluorina, chlorin* or bromine, in particular f1UOI ine or chlorine, and/or from one to threa of the following group~:
Cl-C4-alkyl, such as methyl, ethyl, propyl, l-methylethyl, butyl, l~methylpropyl, 2-methylpropyl or 1,l-dimethyleth-yl~ praferably methyl, ethyl or 1-methylethyl, in par-ticular methyl;
Cl-C4-haloalkyl, in particular Cl- or C2 haloalkyl, such a~
chloromethyl, dichloromethyl, trichloromethyl, fluoro-methyl, difluoromethyl, trifl.uoromethyl, chloro1uoro-methyl, dichloro1uoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2l2-difluoroathyl, 2,2,2-tri~ oroethyl, 2-chloro-2-fluoroethyl, ~ 5 - O.Z. 0050/41834 2-c~loro-2,2-difluoroethyl, 2,2-dichloro~2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl, preferably difluoromethyl or trifluoromethyl, in particular tri-fluoromethyl;
Cl-C4-alkoxy, such as methoxy, ethoxy, propoxy, 1 methyl-ethoxy, butoxy, l-methylpropoxy, ~methylpropoxy or 1,1-dLmethylethoxy, preferably methoxy, ethoxy, 1-methyl-ethoxy or 1,1-dLmethyletho~y, in particular metho.~y or 1-methylethoxy;
Cl-C4-haloalkoxy, in particular Cl- o:r C2-haloalkoxy, ~uch as chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluorometho~y, chloro~
fluoromethoxy,dichlorofluoromethoxy,chlorodi1uorometh-oxy, 1 fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroe~hoxy, lS 2,2,2-trifluoroe~ho~y,2-chloro-2-fluoroethoxy,2-chloxo-2,2 difluoroethoxy, 2,2-di~hloro-2-fluoroethoxy, 2,2,2-trichloroethoxy or pentafluoroetho~y, preferably di-fluorometho~y or trifluorome~ho~y;
Cl-C4-alkylthio, such as methylthio~ ethylthio, propyl-~0 thio, l-methylethylthio, butylthio, l-methylprop~lthio, 2-methylpropylthio or l,l--dLmethylethylthio, preferably methylthio, or C1-C4-haloalkylthio, in particular C~ or C2 haloalkyl-thio, ~uch as chloromethylthio, dichlorome~hylthio, txichloromethylthio, fluoromethylthio, difluoromethyl-thio, trif luoromethylthio, chlorofluoromethylthio~
dichlorofluoromethy~thio, chlorodifluoromethylthio, 1-fluoroethylthio, 2 fluoroethyl~hio, ~,2-difluoroethyl-thio, 2,2, 2-trif luoroethylthio, 2-chloro-2-fluoroethyl thio, 2-chloro-~,2-difluoroethyl~hio, 2~2-dich:Loro-2-fluoroethylthio, 2,2,2-trichloroQthylthio or penta-fluoroethylthio, preferably difluoromethylthio;
R4 is hydroyen;
halogen, such as fluorine, chlorine, bromine or iodine, ; 35 pre~erably ~luorine, chlorine or brominet in paxticular ~luorine or chlorine;
Cl-C4-alkyl/ such as methyl, ethyl, propyl, 1-methyle~hyl~
~ ' - 6 - O.Z. 0050/~1834 butyl~ l-methylpropyl, 2-methylpropyl or lrl-dlmethyleth-yl, preferably m~thyl, ethyl or l-methylethyl or 1,1 dimethylethyl;
C1-C4-haloalkyl, in particular Cl~ or C2-haloalkyl, such as chloromethyl, dichloromethyl, trichloromethyl, fluoro-methyl, difluoromethyl, trifluoromethyl, chlorofluoro-methyl, dichlorofluoromethyl, chlorodifluoromethyl, 1~
fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2 difluoroe~hyl, 2,2-dichloro-2-fluoroethyl, 2,2,2 tri-chloroethyl or pent~fluoroethyl, preferably difluorometh-yl or trifluoromethyl, Cl-C4-alkoxy, such as metho~y, ethoxy, propoxy, 1 methyl-ethoxy, buto~y, l-methylpropoxy, 2-methylpropoxy or 1,1-dLme~hyletho~y, preferably metho~y, ethoxyl 1-methyl-ethoxy or 1,1-dLmethyletho~y, in particular methoxy or l,1-dLmethylethoxy;
Cl-C4~haloalkoxy, in particular C~- or C2-haloalkoxy, such as chloromethoxy, dichloromethoxy, tr.ichloromethoxy, ; 20 fluoromethoxy, difluorometho~y, trifluoromethoxy, chloro-fluoromethoxy r dichlorofluorometho~y,chlorodifluorom2th-oxy, 1 fluorosthoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2/2,2-trifluoroe~hoxy,2-chloro~-fluoroethoxy,2-chloro-2,2-difluoroetho~y, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy or pentafluoxoethoxy, preferably di-fluoromethoxy or ~rifluorome~hoxy;
Cl-C4-alkylthio, such as methylthio, ethylthio, propyl-thio, l-methylethylthio, butylthio, l-methylpropylthio, 2-methylpropylthio or l,l-dLmethylethylthio, preferably methylthio or ethylthiof or C1-C4-haloalkylthio, in particular Cl- or C2-haloalkyl-thio, such a3 chloromethylthio, dichloromethylthio, tr~chloromethylthio, fluoromethylthio, difluoromethyl-thio, triEluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethyl-thio, 2,2,2~rifluoroethylthio; 2-chloro-2-fluoxoethyl-- 7 - o.Z. 0050/41834 thi~, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroe~hylthio, 2,2,2-trichloroethylthio or pentafluoroethylthio, preferably difluorome~hylthio, and R5 and R6 independnetly of one another are each one of the groups stated in general and in particular for R4 or together form a 1,3-butadi0ne-1,4-diyl group which may carry from one to four halogen atom~3, such as fluorine, chlorine, bromine or iodi~e, preferably fluorina, chlor-ine or bromi~e, in particular fluorine or chlorine, and/or from one to three of the following groups:
Cl-C4-alkyl, such as methyl, ethyl, propyl, l-methylethyl, butyl, l-methylpropyl, 2-meth~lpropyl or l,l-dLmethyleth-yl, preferably methyl, ethyl or l-msthylethyl;
Cl C4-ha}oalkyl, in particular Cl- or C2-haloall~yl,~3uch as chloromethyl, dichloromethyl, trichloromethyl, fluoro~
methyl, difluoromethyl, trifluoromethyl, chlorofluoro-methyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2~2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-~-fluoroethyl, 2-chloro~2,2-difluoroethyl, 2,2-dichloro-2-flu~roethyl, 2,2,2-tri-chloroethyl or pentafluoroethyl, preferably ~i~luorometh-yl or trifluoromethyl;
Cl-C4--alkoxy, ~uch a~ methoxy, etho~y, propoxy, l-methyl-ethoxy, butoxy, 1-methylpropoxy, 2-methylpropo~y or 1,1-dLmethylethoxy, preferably methoxy, ethoxy, l-methyl-athoxy or l,l-dLmethylethoxy;
C1-C4-haloalko~y, in particular Cl- or C2-haloalkoxy, such : as chloromethoxy, dichloromethoxy, trlchloromathoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chloro-fluoromethoxy,dichlorofluoromethoxy,chlorodifluorometh-oxy, 1-fluoxoethoxy, 2-~luoroethoxy, 2,2-difluoroethoxy, 2,2,2 trifluoroetho~y,2-chloro-2-fluoroethoxy,2~chloro~
2,2-difluoroethoxy, 2,2-dichloro-2-~luoroethoxy, 2,2,2-trichloroethoxy or pentafluoroethoxy, pref~rably di-fluoromethoxy or trifluoromethoxy;
C1-C4-alkyl~hio, ~uch a~ methylthio, et.hylthio, propyl-thio, l-methylethylthio, butylthio, l-methylpropylthlo, , , , - 8 - O.Z. 0050/4183~
2-methylpropylthio or 1,1-d~nethylethylthio, preferably methylthio or Pthylthio, or Cl-C4-haloalkylthio, in particular Cl- or C2-haloalkyl-thio, such as chloromethylthio, dichloromethylthio, trichloromethylth.io, fluoromethylthio, difluoromethyl-thio, trifluoromethylthio, chloro~luoromethyl~hio, dichlorofluoromethylthio, chlorodifluoromethylthio, l-fluoroethylthio, 2-fluoroethylthio/ 2,2-difluoroethyl-thio, 2,~,2-trifluoroethylthio~ 2-chloro-2-fluoroethyl thio, 2-chloro-2,2-difluoroethylthio, 2,2 dichloro-2-fluoroethylthio, 2,2,2-trichloro~thylthio or penta-fluoroethylthio, preferably difluoromethylthio.
In view of the intended use in the synergis~ic agents, particularly preferred compounds II are those in which ~he substituents have the following meanings-R1 is C1 C~-alkyl as stated above, in particular methyl;
R2 is Cl-C4-alkyl as sta~ed above, in particular methyl or 1 methylethyl, or C3-C6-cycloalkyl as stated above, in particular cyclo-propyl;R3 i~ hydrogen; hydxoxyl;
Cl-C8-alkyl a~ stated abo~e, in particular branched or straight-chai~ Cl-C6-alkyl a~ stated above;
Cl-Ca-alkoxy a~ ~tated above, in particular branched or straigh~-chain Cl C~-alkoxy a~ s~ated above;
C1-C~-alkylamino as stated above, in particular Cl-C6-alkylamino a~ ~tated above;
di-Cl-C8 alkyl~nino as stated a~ove, in particular di-Cl-C4-alkylamino as stated a~ove;
phenyl, phsnoxy or phenylamino, where the aromatic radicals may carry from one to ~ive halogan atoms as stated above, ln particular fluorine or chlorine, and/or from one to thres of the following groups:
Cl-C4-alkyl as stated above~ in particular methyl;
C1-C~,-haloalkyl as sta~ed above, in particular difluoro-methyl or ~rifluoromethyl;
C1-C4-alko~y as ~tated above~ in particular methoxy .
.' .
.
. ~ ; . ,.
g ~ O.Z. 0050/~1834 ethoxy, 1-methylethoxy or l,1-dLmethylethoxy, Cl C4-haloalkoxy as stated above, in particular difluoromethoxy or trifluoromethoxy;
Cl C4-alkylthio as stated above, in particular methylthio or ethyl~hio, and C~-C4-haloalkylthio as stated above, in particular difluoromekhylthio;
R4 is hydrogen;
halogen as stated above~ in particular fluorine or chlorine;
Cl-C4-al3~yl as ~tated above, in particular methyl or 1,1-dLmethylethyl, Cl-C4-haloalXyl as stated above, in particular difluoro-- methyl or trifluoromethyl;
C1-C4-alkoxy as stated above, in particular methoxy or l,l-dimethylethoxy;
C~-C4-haloalkoxy a~ ~tated above, in particular difluoro-; methoxy or trifluoromethoxy;
C~-C4-al~ylthio as ~tatad above, in particular methylthio or ethylthio, or C1-C4-haloalkylthio as stated above, in particular di~luoromethylthio, and R5 and R~ indepedently of one another are each one of ~ha groups ~tated in general and in particular for R4 or togethar fonm a 1,3-butadiene-1,4-diyl group which may carry from one to four halogen atom~ as stated above, in ~rticular fluorine or chlorine, and/or from one to three of the following groups:
C~-C~-alkyl a~ stated above, in pa.rticular meth~l;
C'1~C4-haloalkyl as ~tated above, in particular trifluoro-methyl;
Cl-C4-~al3coxy a~ s~ated above, in particular methoxy;
Cl-C4-haloalkoxy a~ stated above, in particular difluoro-methoxy or trifluorome~ho~y;
C1-C4-al3~ylthio as ~tated above, in paxkicular met.hylthio, and C~-C4-haloalkylthio as stated above, in particular difluoromethylkhio.
- 10 - O.Z. 0050/41~34 Particularly preferred synergistic agen s for regulating plant growth are those which contain an N,N-d ~ ethylpiperidinium salt or an N,N,N trimethyl-N 2-chloroethylammonium salt as the growth-regulating quater-nary ammonium salt.
Particularly prefarred ~nergistic agents of thi~
type are ~hose which contain, in addition ~o the N,N-dime~hylpiperidinium salt~ or N,N;N-trimethyl-N 2-chloro~
ethylammonium salts, an Lmidazolinyl derivative of the general formula II, where R1 is C1-C4-alkyl as stated ahove, in particular methyl;
R2 i~ C1-C4-al ~ 1 as stated above, in particular methyl or l-methylethyl, or C3-C6-cycloal ~ 1 a stated above, in particular cyclo-p~pyl;
R3 is hydrogen; hydroxyl;
Cl-C~-alkyl as stated above, in particular branched or straight-chain C1-C:~-alkyl a~ stated above;
C1 Ct~-alkoxy as stated above, in pa.rticular branched or 2 0 straight-chain C1-C6-alkoxy as st~te~ abo~e, C1-CB-a~ nO a~ stated above, in particular C1-C6-alkylamino as stated above;
di-Cl-Ca-alkylamino a~ stated above, in particular di-C1-C4-alkylami~o as ~tatsd above~ or phenyl, phenoxy or phenylamino, where the aromatic radicals may carry from one to five halogen atoms as ~tated above r in particular f luorine or chlc~rine, _., and/or from one to three of the following groups:
C1-C4-alkyl a~ ~tated above, in particular methyl, Cl-C4-haloalkyl a~ stated above, in particular difluoro-methyl or trifluorome~hyl;
Cl~C4-alko~y a~ statad above, in particular metho~y or ethox~;
C1-C~-haloalko~y a~ stated above, in particular difluoro-methoxy or ~rifluorometho~y;
C1-C4-alkylthio a stated above, in paxticular methylthio or ethylthio, ?
~ O.Z. 0050/41~34 and C,-C4-haloalkylthio as stated above, in particular difluoromethylthio;
R4 is hydrogen or halogen as stated above, in particular fluorine or chlorine, and Rs and R6 independently of one another are each hydrogen;
halogen as stated above, in part:icular ~luorine or chlorine;
Cl-C4-alkyl as stated above, in particular methyl;
Cl-C4 haloal~yl a ~tated above, in particular trifluoro-methyl;
Cl C4 alkoxy a3 stated above, in particular methoxy or I t l-dimethyletho~y;
Cl-C4-haloalkoxy as stated above, in particular difluoro-methoxy or trifluoromethoxy;
Cl-C~-alkylthio a~ ~tated abo~e, in particular methylthiot :~ or Cl-C4-haloalkylthio as stated above, in particular difluoromethyl~hio, or tog0~her form a 1,3-butadiene-1,4-diyl gxoup which may carry from on~ to four halogen atoms as stated above, in : particular fluorine or chlorine, and/or one of the following groups.
Cl-C4 alkyl a~ st ted above, in particular methyl;
: 25 Cl~C4-haloalkyl a~ ~ated above, in particular trifluoro-methyl;
Cl-C4-alkoxy as stated abo~e, in particular methoxy;
C1-C4-haloalkoxy as ~tated above, in particular difluoxo methoxy or trifluorometho~y;
Cl~C4-alkylthio as stated above, in particular methylthio, or Cl-C4~haloalkylthi.o as stated above, in particulax difluoromethylthio.
~'he active ingredients can be applied together or separately, at the ~ame time or in succession~ before, ; 35 duxing or after ~mergence o~ the plan-ts.
In the syner~istic agent~, the weight ratio of ~mmonium salt I to imidazoli.ne derivative II is from - 12 - O.Z. 0050/41834 0.1 . l to 1000 : 1, preferably from 1 : 1 to 950 , 1, in particular from 1.5 : 1 to 920 : 1.
The novel agents can be used, for example, in ~he form of directly sprayable solutions, powders, suspen-sions, including concentra~ed Aqueous, oily or other suspensions or dispersions, emulsions, oil dispersion~, pastes~ dusting agents, broadcasting agents or granules, by spraying, atomi ing~ dusting, broadcasting or pouring.
The application forms depend on the intended uses. Th~y should in any case ensure a very fine distribution of the novel active ingredien~s.
The compounds I and II axe suitable in general for the preparation of directly sprayable solution~, emulsions, pastes or oil dispersions. Suitable inert additive~ are mineral oil fractions ha~ing a medium ~o high boiling point, such a~ kero~ene or diesel oil, and coal tar oil~ and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbon~, eg. toluene, xylene, paraf~inr tetrahydronaphthalene, alkylated naph~halenes or derivative3 thereof~ methanol, ethanol, propanol, butanol/ cyclohexanol, cyclohexanone, chloro-benzene, i~ophorone or strongly polar solvents, such as ~,N-dimethylformamide, dimethyl sulfoxide, N-methyl-pyrrolidone or water.
Aqueous application forms can be prepared from emulsion concenkra~, dispersion~, pastes, wettable powders or water-disper~ible granules by adding water.
For the preparation o emulsion~ t paste~ or oil dispar-sion~, the ~ubstrates, a~ such or dissolved in an oil or sol~ent, can be homogenized in water by means o wekting agent~, adherents, disper~ant~ or emul~ifier~. Howev9r, it i3 also possible to prepare concentrates which con~ist o~ activ~ ~ubstance, wetting agent~, adherents, di~per-san-t~ or emulsl~ier~ and possibly 301~ent or oil and which are suitable for dilution with water.
Suitable surfactant~ are the alkali metal, alkaline earth metal and ammonium salts o~ aromatic - 13 - O.Z. 0050/41834 sulfonic acids, for example lignin-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fatty acids, alkylsulfonate~ and alkylarylsulfonates, alkylsulfate~, lauryl ether sulfates and fatty alcohol sulfates, and ~alts of sulfated hexa-, hepta- and octa-decanols, and of fatty alcohol glycol ethers, condensate~
of sulfonated naphthalene and its derivatives with formaldehyde~ condensates of naphthalene or of naph-thalenesulfonic acids with phenol and formaldehyde~
polyoxyethylene oc~ylphenol ethers, ethoxylated isooctyl,- octyl- or nonylphenol~ alkylphenol polyglycol ether~, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated cas~or oil, polyoxyethylene alkyl ethers or polyoxypropylene, lauryl alcohol polyglycol ether acetate, sorbitol esters, ligninsulfite waste liquors or methylcellulose.
Powders, broadcasting agents and dusting agents can be prepared by mixing or milling the active sub-stances together with a solid carrier.
Granules, for example coa~ed, Lmpregnated and homogeneous granules, can be prepared by binding the active ingredients to solid carriers. Solid carriers are mineral earth~, such as silica gel, silicas, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, kie~elguhr, calcium sulfate, magnesium sulfate, magnesium oxide, milled plastics, fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate and urea3, and vegetable products, such as grain flours, bark meal, wood meal and nutshell meal, cellulosic powders and other solid carrier~.
~he formulations contain from 0.1 to 95, prefer-ably from 0.5 to 90, % by weight of the active in-gredients. The active ingredients are used in a purity of from 90 to lO0~, preferably from 95 to 100% (according to the NMR spectrum).
~he growth regulators or the active ingredients O . Z . 0050/41834 can be applied by the preemergence or postemergence method. If the active ingredients are less well tolerated by certain crops, it i~ pos~ible to use application methods in which the herb.icides are sprayed 5 with the aid of sprayers in such a way that as far as poss.ible they do not come into contact with the leaves of the sensitive crops while the active ingredients reach the leaves of undesirable plant~ g:rowing underneath or the uncovered soil surface ~post-directed, lay by).
The application rates of active ingredient mixture are from 0.01 ~ 0.01 to 2 ~ 0.001, preferably front 0 . 03 + O . 02 to 1 + O . 001, kq/ha of active substance (a.s.), depending on the s~a~on, target plants and stage of grow~h.
The synergistic mixtures can influence virtually all ~tage3 of development of a plant in di~ferent ways and are therefoxe used a~ growth regulators. The range of activity of the plant growth regulators depend~ in particular a) c7}1 the plant ~pecies and variety, b) on the time of application~ ba~ed on the stage of development o~ tha plant, and on the ~ea~on, r) on the place and method of application (for example s~ed dre~ing, ~oil treatment, foliage application or trunk in~ection in .he case of trees), d) on climatic ~actors, eg. temperature, amount of _ precipitation and also length of day and light inten~ity, e) on the soil quality ~including fertilizer applica-tion), f) on the formulation or application form of the active ingredient and finally g) on the ~oncen~rations in which ~he active substance is used.
From ~he various possibl.a applications of the novel agents in cultivation, in agriculture and in hortictllture, ~ome are mentioned below.
- 15 - o.Z. 0050/~1834 A. The vegetative growth of the plant~ can be greatly inhibited with the compounds which can be used according to the invention, this being manifested in paxkicular in a reduction in the growth in length. The treated plants accordingly h ve a stunked growth; more-ov~r, a darker leaf coloration is ob~erved.
Reduce~ intensity of growth of yrasses along road edges, hedges and canal banks and on lawn area~, such as parks, sports grounds, orchards, ornamenkal lawn~ and airfield~, proves advantageous in practice, enabling the labor-inten~ive and expensive cutting of lawns to be rsduced.
The increase in the strength of crop~ su~c~ptible to lodging, such a~ cereals, corn, sunflowers and soy-bean, is also of economic interest. The re~;ultingshortening and strengthening of the stem reduce or slLminate the danger of lodging (of bending) of plants - under unfavorable weather conditions prior to harvesting.
The u~e of growth regulator~ for inhibiting the growkh in length and for changing $he tLme of ripening of ootton iB also importan~. This permit~ completely mechanized harvesting of thi~ important crop.
In the ca3a of fruit tree~ and other trees, the growth r~gulators permit a reduction in cutting cost~.
~oreover, the alternance of fruit trees can be broken by growth ragulators.
The lateral branching of the plants can also be increased or inhibited by the u~e of grow~h regulators.
Thi~ is of interest if, for example, in the case of tobacco plants, it i~ intended to inhibit the formation of ~ide ~hoot~ in favor of leaf growth.
The ~rost rasi~tanco can also be considerably lncrea ed with growth regulator3, for example in wintar rape. On the one hand, the growth in length and the development of a leaf or plant mas~ which i3 too luxuri-ant (and hence particularly su~ceptible to fro3t) are inhibited. On the other hand, the young rape plants are 16 - O.Z. OOS0/41834 held back in the vegetative stage of development after sowing and before the onset of the winter frosts~ in spite of favorable growth conditionst This also elLmina tes the danger of fro~t to plants which tend to ~xhibit a premature decline in ~he inhibition of blooming and to go over into the genPrative phase. In other crops too, for sxamplP winter cereals, it is advantageous if the stocks are well tillered in the fall as a result of treatment ~ith novel compounds bul: do no~ en~er thP
winter with too luxllriant a growt.h. This makes it possible to avoid high sensitiYity to frost and, owing to the relatively small leaf or plant mass, attack by various diseasP~ ~ fox example fungal disease). Inhibi tion of the vegetative growth furthermore permits denser planting of the soil in the case of many cxop~, making it possible to achieve a greater yiel , ba~ed on soi:L area.
. The growth regulators make it possible to achieve greater yield both of plant part~ and of plant in-gredient~. For example, it i~ po ~ible to induce the grow~h of laxger amounts o bud~, blooms, leaYes, fruits, seeds, roots and tuber~, to increase the content of sugar in sugar beet~, sugar cane and citru~ fruits, to increase . the protein content of cereal~ or soybean or to stLmulate greater lat~x flux in rubbsr tree~.
By intervening in the plant metaboli~m or by prcmoting or inhibiting vegetative and/or generative growth, -the synergistic agents can result in increased yield~, C. Finally, both shortening or lengthening of the 8taga9 of development and acceleration or re~ardation o~
the ripening of the haxvested plant parts bsfore or after harve~ing can be achLeved with plant growth regula~or~.
For example, it is of economic interest to facilita~e harve~ting, thi~ being pe~litted by con-centrated dropping or reduction in ~the adhesion to the tree in the ca~e of citrus fruit~, olive~ or other specie~ and varieties ~f pomes, drupes and hardshall ;
- 17 ~ O.Z. 0050/~1834 fruit. The same m~chanism, ie. promotion of the forma-tion of absci~sion tissue between the fruit or leaf part and the sprout part of the plant is also essential for readily controllable defoliation of crops such as for example cotton.
D. Furthermore, the water consumption of plants c~n be reduced with growth regulators. This is particularly important for agricultural areas which have to be artifi-cially irrigated at great expense, for example in arid or semiarid regions. By using the novel ~ubstances, it is po~sible to reduce the intensity of irriga~ion and hence to carry out more economical farming. Under the influ-ence of growth regulators, the available water is bet~er utilized becau~e, in~er alia, 15 - ~he extent of opening of the stomata is re~uced, - a thicker epidermi~ and cuticula are formed, - root penetration o~ the soil i~ improved and - the microclLmate in the crop is advantageou~ly affected by more compacted growth.
The novel synergis~ic agents c~n be fed to the crops both via the seed ~as seed dre~sings) and via the soil, ie. through the root and, particularly preferably, via the foliage by spraying.
Because of the good toleration by plants, the application rate can ba greatly varied.
In view of the wide range of applica~ion methods, the novel agents can be used in cere 1 crops and cotton.
The synergi~tic effect can be determined by the formula of S.R. Colby (Wa~ds 15 (1967), 20~2) E = X ~ Y - X Y / 100 where the variables have th~ following meanings:
X 18 the ~ea~urable effect of the active ingredient I at an applica~ion .ra~e ~a], ; Y is the mea8urable efEect of the active ingredient II at an appl~cation rate ~b] and is the expected measurable efect of a mixture of active ingredient I at the application rate ~a] and of j;, , ! , ~;, . ..
- 18 ~- O.Z. 0050/41834 active ingredient II at the application rate ~b].
From the difference between the expected v~lue ~
according to Colby and the measured value, it is possible ~o determine whether there is a synergistic efect (reinforcement of the effect ox increase of activity) or an antagonistic effect (weakening of the effect or reduction in activity), or if there are merely additive effec~s on the activity, this being the case if the two values correspond.
The Lmproved biological action of the mixtures compared with the individual substances in cereal crops and cotton can be demonstrated in field trials.
Various mix~ures of th~ following compouncls were inves~igat~d:
A
N~N,N~Trimethyl-N-~-chloroethylammoniumchloride(chloro-mequat chloride) N,N-DLmethylpiperidinium chloride ~mepiquat chloride) C
2-~4-Isopropyl-4-methyl-5-oxo-2-imidazolin 2-yl)-3-quinolinecarbo~ylic acid (imazaquin) D
I~opropylammonium 2-(4-isopropyl-4-methyl-S-oxo-2-imidazolin-2~yl)~3-nicotinecarboxylate (imaæapyr) : E
5-Ethyl 2-(4-isopropyl-4-methyl 5-oxo-2-imidazolin 2 yl)-3 nicotinecarbo~ylic acid (imazethapyr) ~he trial~ were carried out on plots, each measuring 12.5 m2 (cereals) or 50 m2 (cotton), with 4 replicates in each ca~e. Cultivation, ~ertilizer ap-plication and the use of crop protection agent~ again~t growth of weeds and attack by fungi and by in~ect pes~s were carried out in a manner conventional ~or t~le location.
The novel agent~ were applied by the post-emergence method (3.5 bar, 400 l/ha of water).
~ '` l"`1 r r - 19 - - Z ~ 0(~50/41~33 The ~bovemPntioned cexeal trial~ show that the novel mixtures are clearly superior to the known mixture A ~ C (EP-A-149 083). Furthenmore, Ta~le 2 shows that a mixture consisting of two diferent quaternary ammonium compounds with a triazole has an action superior to that of ~he known combination of A + C.
TABL~ 1 Crop: Winter barley (variety: Marinka) Type of soil: Clayey loam Sowing: Saptember 28, 1988 Treatment: March 28, 1989 Evaluation: Plant damage Nay 12, 1989 Height of growth May 17, 1989 Sub~tance g/ha of Plant Height of grow~h active damage cmDif~erence rom ingredient % control ~ (cm)_ Control - 0 102.1 A 690 0 101.60.5 D 10 5 72.5- 29.6 A + D 6gO ~ 5 6 71.9 - 30.2 A + D 690 ~ 10 6 57 4 6 - 44.5 A + D 690 ~ 20 11 41.4- 60.7 A ~ C 759 ~ 16.5 3 84.0- 18.1 ~ ~ C 1150 + 25 10 78.9- 23.2 - 20 - OOZ~ 0050/4183 Crop: Winter wheat (variety Baroudeur) Type of soil: Clayey sand Sowing: October 2, 1989 Txeatm~nt: March 28, 1990 Evaluation: Plant damage May 17, 1990 Height of growth June 5 t 1990 Substance g/ha of Plant Height of growth active damage cm Difference from ingredient % control ~ . (cm) Control 0 0 108.0 A + E 920 + 1 0 100.8 - 7.2 A + E 920 t 2 0 99O2 - 8.8 A + E 920 ~ 4 0 99.8 - 8.2 ?
A ~ B ~ E 690 + 230 ~ 20 100.5 - 7.5 A + C 920 + 2 0 101.0 7.0 T~BLE 3 Crop: Winter wheat (varietyO ~axoudeur) ~ype of ~oil: Sandy loam Sowing: October 12, 1989 Treatment: March 5, 1990 Evaluation: Plant da~age June 6, 1990 : Internodal length Ju~e 6, 1990 Ear length June 6, 1990 Substance g/ha o Plant Internodal length Ear length active damage cm Dif~erence cm Difference ingredient ~ fxom con~rol From control cm cm ~
Control 0 a 5.2 8.4 A ~ C 920 -~ 2 0 3.B - 1.4 8.3 ~.l A -~ E 920 ~ 2 0 3.5 - 1.7 8.5 +0,1 . . :
:., -. , , ~ . '' :` :
- 21 - O.Z. 0050/41834 Crop: Winter wheat (variety: Baroudeur3 Type of soil: Sandy loam Sowing: October ~, 1989 Treatments March 1, 1990 Evaluatîons Plant damage May 10, 1990 Height of yrowth May 10, 1990 Substance g/ha of Plant Height of growth active damage cm Difference from 13 ingredient ~ con~rol ~cm) Control 0 0 96.7 A ~ C 920 + 2 0 ~7.6 ~ 9.1 : 15 A + E 920 ~ 1 0 86O2 ~ 10.5 A + E 920 ~ 4 0 86.9 - 9.8 _ , - 22 - O. 2 . 0050/4183 Crop . Winter wheat ( vari ty: Rraka Type of soil: Loamy sand Sowing : November 7, 1 9 8 9 Treatment: April 2, 1990 ~valuation: Plant damage June 6, 1990 Height of growth June 6, 1990 Substance g/ha of Plant Height of growth active damage cm Diffç?rence from ingredien~ % control ( cm Control 0 0 117 . 0 B 690 0 107 . 0 - 10 . 0 1~ C 5 0 11~.5 ~ 1.5 B ~ C 690 + 2 . 5 0 lG6 .1 -10 . 9 A + C 690 ~ 15 0 106 . 9 - 10 .1 EXANPI.ES 6 AND 7 The ~ynergistic e~fect of ~he mixture A + D is demon~trated using barley. It is noted that the addition oiE > 10 g/ha of active ingredient o~ ~ubstance D can lead to plant damage.
.
' ' , - 23 - O.Z. 0050/41834 Crop: Su~mer barley (variety: Gimpel) Type of ~oil: Clay Sowing: March 20, 1989 Treatment: May 18, 1989 Evaluation: Plant damage June 2, 1989 Height of growth Juns 12~ 1989 Substance g/ha of Plant Height of growth active damage cm Difference from ingredient % control ~cm) Control 0 0 101.2 A 690 0 9fi.9 ~ 4,3 D 10 5 55.6 - 45.6 A ~ D 6~0 ~ 5 7 44.6 ~ 56.6 A ~ D690 ^~ 10 8 42.9 - 58.3 A + D690 t 20 8 42.5 - 58.7 TABL~ 7 : 20 Crops Winter barley (variety: Igri) Type of soil: Very clayey loam Sowingo September 22, 1988 Trea~ment: Rpril 21, 1990 Evalllation: Plant dama~e May 15, 1989 : 25 Height of g~owth MAY 22, 1989 Substance g/ha of Plant Height of growth _ active damage cm Difference from ingredien~ % control (cm) .... ~
Control 0 0 111O2 ~90 0 111.2 0 D 10 12 82.0 - 29.2 A + D 690 ~ 10 21 71.2 - 40.0 A ~ D 690 -~ 20 54 63.8 - 47.4 _ ~4 ~ 0.2. 0050/41~34 ~XAMPLES 8 TO 10 In the case of wheat and barley, the mixture A -~
E also leads to synergistic shortening of the stem, im-proved strength and correspondingly greater yields.
Crop: Summer wheat (variety: Ralle) T~pe of soil: Clay Sowing: March 20, 1989 Tre~tmen~. May 18, 1989 Evaluation: Plan~ damage June ~, 1989 Height of growth June 130 1989 Substance g/ha of Plant Height of growth active damage cm Differ~:nce from ingredient ~ control (cm) Control 0 0 7g.8 A 690 0 63.0 - 16.8 E 10 0 7~.8 - 1.0 A + E 690 ~ 5 0 50~1 - 19.7 A + E69~ ~ 10 0 57.8 - 22.0 E690 + 20 4 56.0 - 23.8 TABL~ 9 Crop: Summer wheat (variety$ Ralle) Type of soil: Loam~ ~and Sowing~ February 21, 1989 Tre~ment: ~ay 12, 1989 Evaluation: Plant damage Jun~ 21, 1989 Height of growth Augu~t 3, 1989 Substanca g/ha of Plant Height o~ gxowth active damage cm Differerlce from ingred.ient % control ~cm) Control0 0 36.2 6~ 0 36.8 ~ 0.~
E 10 0 3~.5 - 1.7 '' ' .
.
- 25 - O.Z. 0050/41834 A + E 690 ~ 10 0 39O1 + 2.9 Crop: Winter barley (varietyo Igri~
Type of soil: Very clayey loam Sowing: September 22, 1989 Treatment/ April 21, 1989 Evaluation: Plant damage May 15, 1989 Lodging July 5, 1989 Grain yield 3uly 11, 198g 10 Substance g/ha of Plant Lodging/ Grai~ yield/
active damage difference ~iff~rence ingreclient from control frc~ con~l % ~%] [%]
. . .
Control0 0 46 75.5 690 0 48 + 2 69.7 5.8 0 ~ + ~ 69.3 - 6.2 A + E690 + 10 0 34- 12 76.9 ~ 1.4 A + E690 + 20 0 3610 76.2 ~ 0.7 Mixkures consisting of compounds B + C lead to a synergistic inhibition of growth in barley, whsat and cotton. The resulting improved strength is illu~trated by Exampl~ 13.
- 26 - 0.~. OGSO/41834 TABLE ll Crop: Summer wheat (variety Ralle) Type of ~oil: Clay Sowing: March 20, 1989 Treatment: May 19, 1989 Evaluation: Plant damage June 22, 1989 Height of growth June 13, 1989 Substance g/ha ofPlant Height of growth activedamage cm Difference from ingredient ~ co~trol (cm) .. _ . . ~
ControlO 0 80.6 B 690 0 66.0 ~ 14.6 C 10 0 ~l.O + 0.4 : ~ ~ C690 + lO O 61.5 - 19.1 B + C690 + 20 7 49~8 - 30.8 ~ABL~ 12 Crops Winter wheat (variety: Kraka) Type of soil: Loamy sand Sowing: November 7, 1989 Tr~atment: April 30, 1990 . Evaluation- PLant damage June 5, 1990 Heigh~ of growth June 5, 1990 Substance g~ha ofPlant Haight of growth active damage cm Diff~rence from _ ingredient ~ control (cm) Control O 0 9S.1 B 690 0 86.0 - 9.}
C 5 0 95.4 ~ 0.3 B + C 690 ~ 1.25 0 80.3 - 14.8 B + C 6gO ~ 2.5 0 84.0 - 11.1 B + C 690 + 5.0 0 84.5 - 10.6 ,, .
- 27 - O.Z. 005~/41834 Crop: Summer barley ( varie-ty O Gimpel ) Type of soil: Clay Sowing O Marc h 2 0, 1 9 8 9 Treatment: May 18, 19 8 9 Evalua~ion: Plant damage June 2, 198 Height of growth :rune 12, 198 Lodging July 2 4, 19 8 9 Sub~tance g/ha of Pla.nt Height o:E Lodging~
active damage growth~ dif ference ingredient ~ difference from control from control [cm]
[cm]
Control 0 0 95 . 4 38 B 690 0 94 . 4 -1 G 0 4g + 11 C 10 0 91 O 0 -4 . 4 ~0 ~ 2 B + C 690 + 5 0 82 . 2 -13 . 2 0 - 38 B ~ C 690 + 10 14 61. 6 -33 . 8 0 - 38 B + C 690 ~ ~0 14 S4 ~ 8 -40 . 6 0 - 38 Crop: Cotton (variety: SJ - 2 ) Type o~ soll s Sandy loa~
Sowing: ~ebruary 24, 1989 25 Treatmen$ - June 2~, 198g Evaluations Plant damagl3 July 6, 1989 Heiçrht of growth October 5, 1989 Sub~tance ~/ha of Plant Height of growkh active damage cm Difference from ingredient ~ control ~cm]
Control 0 0 125 . 0 B 30 0 116 . 2 -8 . 8 C 10 0 12~.2 ~1.2 B+ C 30 ~ 5 0 ill . 2 -13 . 8 B~ C 30 ~10 0 110 . 5 -14 . 5 13+ (~ 30 ~~0 0 107 . 5 -17 . 5 ,.i j .,,, ,1,.
- 28 - O.Z. 0050/~1834 CropO Cotton (variety- Stoneville sa5 ) Type of soil: Sandy loam Sowing: May 26, 1989 Treatment: July 24, 1989 Evaluation: Plant damage July 31, 1989 Substance g~ha of Plant Height of growth active damage cm Differ~nce from ingredient % control [cm]
Control 0 0 121.2 B 60 0 111.0 - 10.2 ~ 10 0 122.8 + 1.6 B ~ C 60 + 5 0 112.5 - 8.7 B ~ C 6Q + 10 0 lOg.8 - 11.4 B ~ C 60 + 20 0 107~5 - 13.7 Mixture~ o substances B + ~ also lead to a æmaller plant height and grea~er yield~ in the case of barley, wheat and cotton.
~ Crop: Summer wheat (variety: Ralle) .~ Type of soil 5 Loamy sand Sowing: Augus~ 15, 1989 Z5 ~reatment: August 15, 1989 Evaluations Plant damage June 2, 1989 ~Ieight of growth A~gust 3, 1989 Sub~tance g/ha of Plant Hsiyht of growth active dama~e cm Dif~erence from ingredient % control [cm]
Control 0 0 38.0 B 690 0 40.5 -~ 2.5 D 10 0 38.4 + 0.4 B -~ D690 + 5 0 44.6 + 6.6 B -~ D690 -~ ln 0 40.1 + 2.1 B + D690 t 20 5 31.0 - 7.0 I `' ` ~ "' . ' ! .
- 29 - O.Z. 0050/41834 Crop: Summer barley (~ariety: GLmpel) ~ype of soil: Clay Sowing: March 20, 1989 Treatment May 18, 19 8 9 Evaluation: Plant damag~ June 2, 1989 Heigh~ of grow~h June 12, 1989 Substance g/ha of Plant Height of growth active dam~ge cmDifference from ingredient % control ~cm]
Control 0 0 g5.4 B 690 0 94.4 - 1.0 D 10 5 51.8 - 43.6 B + D 690 -~ 10 0 43.9 - 51.5 B + D 690 + 20 6 43.5 51.9 TABL~ 18 Crop: Cotton (variety~ ~C - 510) Type of soil: Loam Sowing^ ~ebruary 28, 1989 Treatment: June 27, 1989 Evaluation: Plant damage July 6, 1989 Height of growth July 26, 1989 Substance g/ha of Plant Height o~ grow~h ac~ivQ damage cmDifference from ingredient % control [cm]
Control 0 0 g6.6 B 30 0 88.7 - 7.g D 10 6 96.6 0 B ~ D 30 ~ 5 3 a4 . 1- 12 ~ 5 B ~ D 30 ~ 10 6 83.4 - 13.2 B -~ D 30 ~ 20 8 80.8 - 15.8 EXAML~LES 19 TO 25 In tha ca~e of baxlsy, oat~, wheat and cotton, it wa~ al~o possible to reduce the height of growth, reduca lodging and increa3e the yield by mixturQs of substances :~ Y'1 - 30 - O.Z. 0050/41834 B ~ E.
TABLE lg Crop~ Summer wheat (variety: Ralle) Type of soil: Clay Sowing: March 20, 1989 Treatment: May 19, 1989 Evaluation: Plant damage June 2, 1989 Height of growth June 13, 1989 Sub~tance g/ha of Plant Height of grow*h active damage cmDiffer~nce from ingredient % control [cm]
Contxol 0 0 80.6 B 690 0 66.0- 14.5 E 10 a 8~oO+ 1.4 B ~ E690 ~ 5 9 60.0- 20.6 ; B + E690 * 10 0 57.023.6 690 + ~0 5 54.0~ 26.6 TA~LE 20 -~ 20 Crop: Winter wheat ~variQtys Xanzler) ~ype of soil: Clay Sowing: ~ctober 4, 1989 : Treatment: April 5, 1990 E~aluation: Plant damage June 5, 1990 Height of growth June 5; 1990 Sub~tanc~ g/ha of Plant Haight of gr~wt;h active damage cm Di~ference frvm inyredient % control [cm]
Control 0 0 122.9 B 690 0 117.2 - 5.7 E 5 0 122.8 - 0.1 B + ~ 690 + 1.25 0 113.2 - 9.7 B + ~ 690 t 2.5 0 114.8 ~ 8.1 B ~ 90 t 5 0 113.4 - 9.5 , - '' ~ ' :
~ ~ .
- 31 - O.Z. 005~/4183 Crop: Winter wheat (variety: Kraka) Type of soil: Loamy sand 50wing: November 7, 1989 Treatment: May 2, 1990 Evaluation: Plant damage June 5, 1990 Height of growth June 5, 1990 Substa~ce g/ha o~ Plant Height of grow*h active damage cm Difference fro~
lD ingredient % con~rol ~cm]
Control a 0 97.9 B 690 0 88.7 - 9.2 E 5 0 ~9.1 ~ 1.2 B ~ E 690 ~ 2.5 0 86.0 - 11,.9 B ~ E 690 -t 5 0 85.4 12.5 TAB~E 22 Crop: Oats (variety. Fl~mingsnova) Type of soil: Sandy lo~m Sowing. March R, 1990 Trea~ment: May 131 1990 : Evaluation: Plant damage June 8, 1990 . Height of growth June 8~ 1990 ; Sub~tance g/ha of Plant Height of growth active damage cm DifferQnce from ingredient % control [cm]
Control0 0 97.5 B 690 0 91.9 - 5.6 E 5 0 95.8 ~ 1.7 B + E690 + 5 0 89.1 - 8.4 - 32 - O. Z . 0050/41834 Crop: Summer barley ( variety: Gimpel ) I~ype of soil: Clay Sowing: March 20~ 1989 Treatment: May 18, 19 8 9 Evall~ation~ Plant damage June 2, 1989 Height of growth June 12, 1989 Lodging J uly 2 4, 1 9 8 9 Substance g/ha of Plant Height of Lodging/
active damage growt:h/ dif feren~e ingredient % difference from con f rom control trol [ % ]
[cm]
Control 0 0 95 . 4 38 B 690 0 94 . 4 - 1. 0 49 ~ 11 E 10 0 93.1 - 2.3 42 +4 E~ ~ E 690 ~ 10 0 91. 6 -3 . 8 36 - 2 B ~ E ~9û ~ 20 6 67 . 5 -27 . 9 0 - 38 2 û TAB~l~ 2 4 Crop s Cottoll ( variety: S~ - 2 ) Type of ~oil: Sandy loam Sowing : Fe~ruary 2 4, 1 9 8 9 I'reatment o June 2 7, 19 8 9 . ~ 25 Evaluation: Plant dsmage July 6, 198~
HQight of growth October 5, 1989 Sub~tance g/ha of Plant Height of grow~h ac:tive damage cm Di~erence from ing-redient % control ~cm]
3 0 ~
Control 0 0 125 . 0 B 30 0 116.2 8.8 2 130 . 0 + 5 . 0 B -1 E 30 + 5 0 111. 2 13 . 8 3S B ~ E 30 ~ 10 ~ 111. 2 -13 . 8 ~ 1 - 33 -O.Z. 0050/41~34 Crop~ Cot~on (variety: GC - 510) Type of soil: Loam Sowing~ February 28, l9B9 Treatment: June 27, 1989 Evaluation: Plant damage June 6~ 1990 Yield of seed cotton June 6, 1990 Sub~tance g/ha of PlantYield of seed co~ton active damagekg/ha Difference ~rom ingredient ~ control (kg/ha) :
Con~rol 0 0 3233 B 30 0 3375 + 142 30 + 5 ~ 3~53 + 22~
B + E 30 ~ 10 4 4003 ~ 770 B ~ E 30 + 20 3 2693 ~ 540
O.Z. 0050/41834 Synerqistic aqents for requla~in~ ~lant qrowth The present invention relates to agent~ for regulating plant growth, containing a synergistic mixture of one or more growth-ragulating qua~ernaxy ammonium salts from the group consis~ing o~ the compounds I, comprising N,N-dLmethylazacycloheptani~m salt~, N,N
dimethylpipexidinium salts, N,N~dimethyltetrahydro-pyridazinium salts, N,N,N-trimethyl-N-~-chloroethyl-ammonium salts~ N-methylpyridinium salts and N,N-dLme-thylpyrrolidinium salts, and an imiclazolinyl derivativeof ~he ~eneral formula II
R 5~COR 3 I I
R 6 N~R 1 HN O
wh~re R1 i~ Cl-C4-alkyl, R2 i~ Cl-C4-alkyl or C3-C~ CYC1G_ alkyl, R3 iS ~ydrogen, hydro~yl, Cl-Cl2-alkyl, Cl-Cl2-alkoxy, C1-C1~-alkylamino, di-Cl-Cl2-alXylamino or is phenyl t phenoxy or ph~nylamino, where the aromatic radicals may carry from one ~o five halogen atoms and/vr from one to three of the following group~: Cl-C4-alkyl ~
Cl-C4-haloalkyl, Cl-C4-alkoxy, C~-C4-haloalko~r, C~ 4-alXylthio or C1-C4-haloalkylthio, R4 is hydrogen, halogen?
Cl-C4-alkyl, Cl-C4-haloallcyl, Cl-C,,-alkoxy, Cl-C4-haloalkoxy, Cl~C4-alkylthio or C1-C4-haloalkylthio and ~5 and R~ lndepend~ntly of one another are each one of the group~ ~tated for R4 or together form a 1,3-butadiene-1,4-diyl group which may carry from one to four halogen atomsand/or from one to three of the following groups: C1-C4-alkyl r C1-C4-haloalkyl, Cl-C4-alkoxy, Cl~C4 haloalko:~y, Cl-C4-alkylthio or Cl-C4-haloal~ylthio, and inert additives.
The present invention furthermore relates to methods ~or regulating plant growth with these agents.
~ uaternary ammonium compound~ are disclosed in the literature as plant growth regulators (DE-A 22 07 575). The li~erature alco describes 'j ,~ ~" ~
- Z - O.Z. 0050~41834 imidazole deriYatives as herbicides ~DE-A 31 21 736).
Mixtures of N,N,N-trimethyl-N ~-chloreethylammonium s~lts and 2-(4-isopropyl-4-methyl-5-oxo-2-Lmidazolin-2-yl)-3-quinolinecarboxylic acid having growth-regulat.ing properties are ~lso known (EP-A 149 083~.
I~ is an ob~ect of the present in~ention to provide novel effective ~ynergistic mixtures for regula~-ing plant growth.
~e have found that this ob~ect is achieved by ~he synergistic mixtures defined at the outset. Method~ ~or u~ing these mixtures as plant growth regulators were also found.
In view of the intended use in the novel syner-~istic growth-regulating agents, suitable substituents of the c~mpound~ II are the following radicals~
R1 is Cl-C4-alkyl, such as methyl, ethyl, propyl, 1-methyleth~l, butyl/ l-methylpropyl, 2-methylpropyl or dimethylethyl, preferably methyl, ethyl or 1-methyl ethyl, in particular methyl or l-methylethyl;
R~ is Cl-C4-alkyl, such as me~hyl, ethyl, propyl, 1-methylethyl, butyl, l-methylpropyl, ~-methylpropyl o~
1/l-~imethylethyl, preferably methyl or ethyl, in par-ticular meth~1, or C3-C6-cycloal~yl, ~uch a~ cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, preferably cyclopropyl or cyclopentyl, in particular cyclopropyl;
: R3 iY hydrogen;
C1-C12-alkyl, prefsrably branched or straight-chain Cl-C6-alkyl, such as methyl, ethyl, pxopyl, l-methyllethyl, 3~ butyl, l-mathylpropyl, 2-methylpropyl, 1,1-dLmethyllethyl, pentyl., 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2 dimethylpropyl, l-ethylpropyl~ hexyl, 1,1-dimethylpropyl, 1,2-di~ethylpropyl, 1-m~thylpentyl, 2-mekhylpentyl, 3-methylpentyl, 4~methylpentyl, 1,1-dimethylbutyl, 1,2-dlmethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-d:Lmethylbutyl~ 3,3-dimethylbutyl, l-ethylbu~yl, 2-e~hyl-butyl, l,1,2-trimethylpropyl, 1,2,2-trimekhylpropyl, - 3 - O.~. 0050~41834 1-e~hyl-1-methylpropyl and l~ethyl-2-methylpropyl, in particular br~nched or straight-chain Cl-C4-alkyl, such as methyl, ethyl, propyl, l-methylethyl, butyl, l-methyl propyl, 2-methylpropyl or 1,l~dLmethylethyl;
C~-C12-alkoxy, preferably branched or straight chain C~-C6-alkoxy, such as methoxy, ethoxyl propoxy, 1-methyl-ethoxy; butoxy, l-methylpropoxy, 2-me~hylpropoxy, 1,1-dLmethylethoxy, pentyloxy, 1-methylbutoxy, 2-methyl~
butoxy~ 3-methylbutoxy, 2,2-dLmethylpropoxy, 1-ethylprop-oxy, he~yloxy, l,l-dLmethylpropoxy, 1.,2-dLmethylpropoxy, l-me~hylpentyloxy, 2-methylpentylo~y/ 3-mathylpentyloxy, 4~Nethylpentyloxy, 1,l-dimethylbutoxy, 1~2-dimethyl-butoxy, 1~3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbuto~y, 2-lS ethylbuto~y, 1,1,2-trimethylpropo~y, 1,2,2-trimethyl-propo~y, l-ethyl-1-met~ylpropoxy or 1-ethyl-2-methyl-propoxy/ in particular branched or straight-chain Cl-C4-alkoxy, such as methoxy, etho~y, propoxy, l-methylethoxy, : ~uto~y, l-me~hylpropoxy, ~-methylpropo~y or 1,1-dLmethyl-ethoxy;
Cl-Cl2-alkylamino, in particular C1-C6-alkylamino, such as methylamino, ethylamino, propylamino, l-methylethylamino, butylamino, 1-methylpropy~lamino, 2-methylpropylamino, 1,~ dimethyle~hylamino, pentylamino, 1 methylbutylamino, 2-methylbutylamino~3-methylbutylamino,2,2-dLmethylprop-ylamino, l~ethylpropylamino, hexy~lamino, 1,1-d~nethyl-propylamino, 1,2-dimethylpropyl2mino, l-methylp~antyl-amino, 2-m~thylp~antylamino, 3-methylpentylamino, 4-methylpen~ylhmino, ~ dimethylbutylamino, 1,2-dlm~athyl-butylamino, 1,3-dimethylbutylamino, 2,2-dimethylbutyl-amino, 2,3-dimethyl~u~ylamino, 3,3-dimeth~lbutylamino, 1-ethylbutylamino~ 2 ethylbutylamino; 1,1,2-trimethylprop-yl~nino, 1,2,~-trimethylpropylamino, 1 ethyl-l-methyl-~,, propylamino and 1-ethyl-2-methylpropylamino;
di-C1-C12-alkylamino, in particular di-C~-C~-alkylamino, preferably di-Cl-Cb-alkylamino, ~uch a~ N,N~dimethyl~mino, diethylamino, N,~-dipropyl~mino, ~,N-di-(1-methyl-., ;~
, ., ,, .
- ~ - O.Z. 0050/41~34 ethyl)amino, N,N-dibu~ylamino, N,N-di~(1 methylpropyl)~
amino, N,N-di-~2-methylpropyl)-amino, N,N-di-(1,1-dLmethylethyl)-amino, N-ethyl-N-methylamino, N-methyl-N
propylamino, N-methyl-N-(l-methylethyl)-amino, N-butyl-N-methylamino, N-methyl-N~ methylpropyl)-amino, N-methyl-N-(2-methylpropyl)-amino, N-(1,1-d~nethylethyl)-N-methylamino, N-ethyl-N-propylamino, N-ethyl-N-(l-methylethyl)~amino, N-butyl-N~ethylamino, N-ethyl-N-(l-methylpropyl)-amino,N ethyl-N-(2-methylpropyl)-amino,N-ethyl-N~ d~nethylethyl)-~mino, N~ methylethyl)-N-propylamino, N-butyl N-propylamino, N-(1-methylpropyl)-N propylamino, N~(2-methylpropyl)- N-propylamino,:N-(l,l-dLmethylethyl)-~-propylamino, N-butyl-N-tl-methylethyl) amino, N~ methylethyl)-N-(1-methylpropyl)-amino, N~
methylethyl)-N (2-methylpropyl)-aminol N-(1,l-dLmethyl-ethyl)-N-Il-methylethyl) amino, N-butyl-N~ methyl-propyl)-amino,N-butyl-N~(2-methylpropyl)-amino,N-butyl-N-(l,l-dimethylethyl)-amino, N~ methylpropyl)-N-(2-methylpropyl)-amino, N-(l,l-dLmethylethyl)-N (1 methyl-propyl)-amine and N-(l,l-dLmethylethyl)-N~(2-methyL-propyl)-amino;
phenyl, phe~o~y or phenylamino, where the aromatic radical3 may carry from one to five halogen atoms, such a~ fluorine, chlorine, bromine or iodine, preferably fluorina, chlorin* or bromine, in particular f1UOI ine or chlorine, and/or from one to threa of the following group~:
Cl-C4-alkyl, such as methyl, ethyl, propyl, l-methylethyl, butyl, l~methylpropyl, 2-methylpropyl or 1,l-dimethyleth-yl~ praferably methyl, ethyl or 1-methylethyl, in par-ticular methyl;
Cl-C4-haloalkyl, in particular Cl- or C2 haloalkyl, such a~
chloromethyl, dichloromethyl, trichloromethyl, fluoro-methyl, difluoromethyl, trifl.uoromethyl, chloro1uoro-methyl, dichloro1uoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2l2-difluoroathyl, 2,2,2-tri~ oroethyl, 2-chloro-2-fluoroethyl, ~ 5 - O.Z. 0050/41834 2-c~loro-2,2-difluoroethyl, 2,2-dichloro~2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl, preferably difluoromethyl or trifluoromethyl, in particular tri-fluoromethyl;
Cl-C4-alkoxy, such as methoxy, ethoxy, propoxy, 1 methyl-ethoxy, butoxy, l-methylpropoxy, ~methylpropoxy or 1,1-dLmethylethoxy, preferably methoxy, ethoxy, 1-methyl-ethoxy or 1,1-dLmethyletho~y, in particular metho.~y or 1-methylethoxy;
Cl-C4-haloalkoxy, in particular Cl- o:r C2-haloalkoxy, ~uch as chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluorometho~y, chloro~
fluoromethoxy,dichlorofluoromethoxy,chlorodi1uorometh-oxy, 1 fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroe~hoxy, lS 2,2,2-trifluoroe~ho~y,2-chloro-2-fluoroethoxy,2-chloxo-2,2 difluoroethoxy, 2,2-di~hloro-2-fluoroethoxy, 2,2,2-trichloroethoxy or pentafluoroetho~y, preferably di-fluorometho~y or trifluorome~ho~y;
Cl-C4-alkylthio, such as methylthio~ ethylthio, propyl-~0 thio, l-methylethylthio, butylthio, l-methylprop~lthio, 2-methylpropylthio or l,l--dLmethylethylthio, preferably methylthio, or C1-C4-haloalkylthio, in particular C~ or C2 haloalkyl-thio, ~uch as chloromethylthio, dichlorome~hylthio, txichloromethylthio, fluoromethylthio, difluoromethyl-thio, trif luoromethylthio, chlorofluoromethylthio~
dichlorofluoromethy~thio, chlorodifluoromethylthio, 1-fluoroethylthio, 2 fluoroethyl~hio, ~,2-difluoroethyl-thio, 2,2, 2-trif luoroethylthio, 2-chloro-2-fluoroethyl thio, 2-chloro-~,2-difluoroethyl~hio, 2~2-dich:Loro-2-fluoroethylthio, 2,2,2-trichloroQthylthio or penta-fluoroethylthio, preferably difluoromethylthio;
R4 is hydroyen;
halogen, such as fluorine, chlorine, bromine or iodine, ; 35 pre~erably ~luorine, chlorine or brominet in paxticular ~luorine or chlorine;
Cl-C4-alkyl/ such as methyl, ethyl, propyl, 1-methyle~hyl~
~ ' - 6 - O.Z. 0050/~1834 butyl~ l-methylpropyl, 2-methylpropyl or lrl-dlmethyleth-yl, preferably m~thyl, ethyl or l-methylethyl or 1,1 dimethylethyl;
C1-C4-haloalkyl, in particular Cl~ or C2-haloalkyl, such as chloromethyl, dichloromethyl, trichloromethyl, fluoro-methyl, difluoromethyl, trifluoromethyl, chlorofluoro-methyl, dichlorofluoromethyl, chlorodifluoromethyl, 1~
fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2 difluoroe~hyl, 2,2-dichloro-2-fluoroethyl, 2,2,2 tri-chloroethyl or pent~fluoroethyl, preferably difluorometh-yl or trifluoromethyl, Cl-C4-alkoxy, such as metho~y, ethoxy, propoxy, 1 methyl-ethoxy, buto~y, l-methylpropoxy, 2-methylpropoxy or 1,1-dLme~hyletho~y, preferably metho~y, ethoxyl 1-methyl-ethoxy or 1,1-dLmethyletho~y, in particular methoxy or l,1-dLmethylethoxy;
Cl-C4~haloalkoxy, in particular C~- or C2-haloalkoxy, such as chloromethoxy, dichloromethoxy, tr.ichloromethoxy, ; 20 fluoromethoxy, difluorometho~y, trifluoromethoxy, chloro-fluoromethoxy r dichlorofluorometho~y,chlorodifluorom2th-oxy, 1 fluorosthoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2/2,2-trifluoroe~hoxy,2-chloro~-fluoroethoxy,2-chloro-2,2-difluoroetho~y, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy or pentafluoxoethoxy, preferably di-fluoromethoxy or ~rifluorome~hoxy;
Cl-C4-alkylthio, such as methylthio, ethylthio, propyl-thio, l-methylethylthio, butylthio, l-methylpropylthio, 2-methylpropylthio or l,l-dLmethylethylthio, preferably methylthio or ethylthiof or C1-C4-haloalkylthio, in particular Cl- or C2-haloalkyl-thio, such a3 chloromethylthio, dichloromethylthio, tr~chloromethylthio, fluoromethylthio, difluoromethyl-thio, triEluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethyl-thio, 2,2,2~rifluoroethylthio; 2-chloro-2-fluoxoethyl-- 7 - o.Z. 0050/41834 thi~, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroe~hylthio, 2,2,2-trichloroethylthio or pentafluoroethylthio, preferably difluorome~hylthio, and R5 and R6 independnetly of one another are each one of the groups stated in general and in particular for R4 or together form a 1,3-butadi0ne-1,4-diyl group which may carry from one to four halogen atom~3, such as fluorine, chlorine, bromine or iodi~e, preferably fluorina, chlor-ine or bromi~e, in particular fluorine or chlorine, and/or from one to three of the following groups:
Cl-C4-alkyl, such as methyl, ethyl, propyl, l-methylethyl, butyl, l-methylpropyl, 2-meth~lpropyl or l,l-dLmethyleth-yl, preferably methyl, ethyl or l-msthylethyl;
Cl C4-ha}oalkyl, in particular Cl- or C2-haloall~yl,~3uch as chloromethyl, dichloromethyl, trichloromethyl, fluoro~
methyl, difluoromethyl, trifluoromethyl, chlorofluoro-methyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2~2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-~-fluoroethyl, 2-chloro~2,2-difluoroethyl, 2,2-dichloro-2-flu~roethyl, 2,2,2-tri-chloroethyl or pentafluoroethyl, preferably ~i~luorometh-yl or trifluoromethyl;
Cl-C4--alkoxy, ~uch a~ methoxy, etho~y, propoxy, l-methyl-ethoxy, butoxy, 1-methylpropoxy, 2-methylpropo~y or 1,1-dLmethylethoxy, preferably methoxy, ethoxy, l-methyl-athoxy or l,l-dLmethylethoxy;
C1-C4-haloalko~y, in particular Cl- or C2-haloalkoxy, such : as chloromethoxy, dichloromethoxy, trlchloromathoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chloro-fluoromethoxy,dichlorofluoromethoxy,chlorodifluorometh-oxy, 1-fluoxoethoxy, 2-~luoroethoxy, 2,2-difluoroethoxy, 2,2,2 trifluoroetho~y,2-chloro-2-fluoroethoxy,2~chloro~
2,2-difluoroethoxy, 2,2-dichloro-2-~luoroethoxy, 2,2,2-trichloroethoxy or pentafluoroethoxy, pref~rably di-fluoromethoxy or trifluoromethoxy;
C1-C4-alkyl~hio, ~uch a~ methylthio, et.hylthio, propyl-thio, l-methylethylthio, butylthio, l-methylpropylthlo, , , , - 8 - O.Z. 0050/4183~
2-methylpropylthio or 1,1-d~nethylethylthio, preferably methylthio or Pthylthio, or Cl-C4-haloalkylthio, in particular Cl- or C2-haloalkyl-thio, such as chloromethylthio, dichloromethylthio, trichloromethylth.io, fluoromethylthio, difluoromethyl-thio, trifluoromethylthio, chloro~luoromethyl~hio, dichlorofluoromethylthio, chlorodifluoromethylthio, l-fluoroethylthio, 2-fluoroethylthio/ 2,2-difluoroethyl-thio, 2,~,2-trifluoroethylthio~ 2-chloro-2-fluoroethyl thio, 2-chloro-2,2-difluoroethylthio, 2,2 dichloro-2-fluoroethylthio, 2,2,2-trichloro~thylthio or penta-fluoroethylthio, preferably difluoromethylthio.
In view of the intended use in the synergis~ic agents, particularly preferred compounds II are those in which ~he substituents have the following meanings-R1 is C1 C~-alkyl as stated above, in particular methyl;
R2 is Cl-C4-alkyl as sta~ed above, in particular methyl or 1 methylethyl, or C3-C6-cycloalkyl as stated above, in particular cyclo-propyl;R3 i~ hydrogen; hydxoxyl;
Cl-C8-alkyl a~ stated abo~e, in particular branched or straight-chai~ Cl-C6-alkyl a~ stated above;
Cl-Ca-alkoxy a~ ~tated above, in particular branched or straigh~-chain Cl C~-alkoxy a~ s~ated above;
C1-C~-alkylamino as stated above, in particular Cl-C6-alkylamino a~ ~tated above;
di-Cl-C8 alkyl~nino as stated a~ove, in particular di-Cl-C4-alkylamino as stated a~ove;
phenyl, phsnoxy or phenylamino, where the aromatic radicals may carry from one to ~ive halogan atoms as stated above, ln particular fluorine or chlorine, and/or from one to thres of the following groups:
Cl-C4-alkyl as stated above~ in particular methyl;
C1-C~,-haloalkyl as sta~ed above, in particular difluoro-methyl or ~rifluoromethyl;
C1-C4-alko~y as ~tated above~ in particular methoxy .
.' .
.
. ~ ; . ,.
g ~ O.Z. 0050/~1834 ethoxy, 1-methylethoxy or l,1-dLmethylethoxy, Cl C4-haloalkoxy as stated above, in particular difluoromethoxy or trifluoromethoxy;
Cl C4-alkylthio as stated above, in particular methylthio or ethyl~hio, and C~-C4-haloalkylthio as stated above, in particular difluoromekhylthio;
R4 is hydrogen;
halogen as stated above~ in particular fluorine or chlorine;
Cl-C4-al3~yl as ~tated above, in particular methyl or 1,1-dLmethylethyl, Cl-C4-haloalXyl as stated above, in particular difluoro-- methyl or trifluoromethyl;
C1-C4-alkoxy as stated above, in particular methoxy or l,l-dimethylethoxy;
C~-C4-haloalkoxy a~ ~tated above, in particular difluoro-; methoxy or trifluoromethoxy;
C~-C4-al~ylthio as ~tatad above, in particular methylthio or ethylthio, or C1-C4-haloalkylthio as stated above, in particular di~luoromethylthio, and R5 and R~ indepedently of one another are each one of ~ha groups ~tated in general and in particular for R4 or togethar fonm a 1,3-butadiene-1,4-diyl group which may carry from one to four halogen atom~ as stated above, in ~rticular fluorine or chlorine, and/or from one to three of the following groups:
C~-C~-alkyl a~ stated above, in pa.rticular meth~l;
C'1~C4-haloalkyl as ~tated above, in particular trifluoro-methyl;
Cl-C4-~al3coxy a~ s~ated above, in particular methoxy;
Cl-C4-haloalkoxy a~ stated above, in particular difluoro-methoxy or trifluorome~ho~y;
C1-C4-al3~ylthio as ~tated above, in paxkicular met.hylthio, and C~-C4-haloalkylthio as stated above, in particular difluoromethylkhio.
- 10 - O.Z. 0050/41~34 Particularly preferred synergistic agen s for regulating plant growth are those which contain an N,N-d ~ ethylpiperidinium salt or an N,N,N trimethyl-N 2-chloroethylammonium salt as the growth-regulating quater-nary ammonium salt.
Particularly prefarred ~nergistic agents of thi~
type are ~hose which contain, in addition ~o the N,N-dime~hylpiperidinium salt~ or N,N;N-trimethyl-N 2-chloro~
ethylammonium salts, an Lmidazolinyl derivative of the general formula II, where R1 is C1-C4-alkyl as stated ahove, in particular methyl;
R2 i~ C1-C4-al ~ 1 as stated above, in particular methyl or l-methylethyl, or C3-C6-cycloal ~ 1 a stated above, in particular cyclo-p~pyl;
R3 is hydrogen; hydroxyl;
Cl-C~-alkyl as stated above, in particular branched or straight-chain C1-C:~-alkyl a~ stated above;
C1 Ct~-alkoxy as stated above, in pa.rticular branched or 2 0 straight-chain C1-C6-alkoxy as st~te~ abo~e, C1-CB-a~ nO a~ stated above, in particular C1-C6-alkylamino as stated above;
di-Cl-Ca-alkylamino a~ stated above, in particular di-C1-C4-alkylami~o as ~tatsd above~ or phenyl, phenoxy or phenylamino, where the aromatic radicals may carry from one to five halogen atoms as ~tated above r in particular f luorine or chlc~rine, _., and/or from one to three of the following groups:
C1-C4-alkyl a~ ~tated above, in particular methyl, Cl-C4-haloalkyl a~ stated above, in particular difluoro-methyl or trifluorome~hyl;
Cl~C4-alko~y a~ statad above, in particular metho~y or ethox~;
C1-C~-haloalko~y a~ stated above, in particular difluoro-methoxy or ~rifluorometho~y;
C1-C4-alkylthio a stated above, in paxticular methylthio or ethylthio, ?
~ O.Z. 0050/41~34 and C,-C4-haloalkylthio as stated above, in particular difluoromethylthio;
R4 is hydrogen or halogen as stated above, in particular fluorine or chlorine, and Rs and R6 independently of one another are each hydrogen;
halogen as stated above, in part:icular ~luorine or chlorine;
Cl-C4-alkyl as stated above, in particular methyl;
Cl-C4 haloal~yl a ~tated above, in particular trifluoro-methyl;
Cl C4 alkoxy a3 stated above, in particular methoxy or I t l-dimethyletho~y;
Cl-C4-haloalkoxy as stated above, in particular difluoro-methoxy or trifluoromethoxy;
Cl-C~-alkylthio a~ ~tated abo~e, in particular methylthiot :~ or Cl-C4-haloalkylthio as stated above, in particular difluoromethyl~hio, or tog0~her form a 1,3-butadiene-1,4-diyl gxoup which may carry from on~ to four halogen atoms as stated above, in : particular fluorine or chlorine, and/or one of the following groups.
Cl-C4 alkyl a~ st ted above, in particular methyl;
: 25 Cl~C4-haloalkyl a~ ~ated above, in particular trifluoro-methyl;
Cl-C4-alkoxy as stated abo~e, in particular methoxy;
C1-C4-haloalkoxy as ~tated above, in particular difluoxo methoxy or trifluorometho~y;
Cl~C4-alkylthio as stated above, in particular methylthio, or Cl-C4~haloalkylthi.o as stated above, in particulax difluoromethylthio.
~'he active ingredients can be applied together or separately, at the ~ame time or in succession~ before, ; 35 duxing or after ~mergence o~ the plan-ts.
In the syner~istic agent~, the weight ratio of ~mmonium salt I to imidazoli.ne derivative II is from - 12 - O.Z. 0050/41834 0.1 . l to 1000 : 1, preferably from 1 : 1 to 950 , 1, in particular from 1.5 : 1 to 920 : 1.
The novel agents can be used, for example, in ~he form of directly sprayable solutions, powders, suspen-sions, including concentra~ed Aqueous, oily or other suspensions or dispersions, emulsions, oil dispersion~, pastes~ dusting agents, broadcasting agents or granules, by spraying, atomi ing~ dusting, broadcasting or pouring.
The application forms depend on the intended uses. Th~y should in any case ensure a very fine distribution of the novel active ingredien~s.
The compounds I and II axe suitable in general for the preparation of directly sprayable solution~, emulsions, pastes or oil dispersions. Suitable inert additive~ are mineral oil fractions ha~ing a medium ~o high boiling point, such a~ kero~ene or diesel oil, and coal tar oil~ and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbon~, eg. toluene, xylene, paraf~inr tetrahydronaphthalene, alkylated naph~halenes or derivative3 thereof~ methanol, ethanol, propanol, butanol/ cyclohexanol, cyclohexanone, chloro-benzene, i~ophorone or strongly polar solvents, such as ~,N-dimethylformamide, dimethyl sulfoxide, N-methyl-pyrrolidone or water.
Aqueous application forms can be prepared from emulsion concenkra~, dispersion~, pastes, wettable powders or water-disper~ible granules by adding water.
For the preparation o emulsion~ t paste~ or oil dispar-sion~, the ~ubstrates, a~ such or dissolved in an oil or sol~ent, can be homogenized in water by means o wekting agent~, adherents, disper~ant~ or emul~ifier~. Howev9r, it i3 also possible to prepare concentrates which con~ist o~ activ~ ~ubstance, wetting agent~, adherents, di~per-san-t~ or emulsl~ier~ and possibly 301~ent or oil and which are suitable for dilution with water.
Suitable surfactant~ are the alkali metal, alkaline earth metal and ammonium salts o~ aromatic - 13 - O.Z. 0050/41834 sulfonic acids, for example lignin-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fatty acids, alkylsulfonate~ and alkylarylsulfonates, alkylsulfate~, lauryl ether sulfates and fatty alcohol sulfates, and ~alts of sulfated hexa-, hepta- and octa-decanols, and of fatty alcohol glycol ethers, condensate~
of sulfonated naphthalene and its derivatives with formaldehyde~ condensates of naphthalene or of naph-thalenesulfonic acids with phenol and formaldehyde~
polyoxyethylene oc~ylphenol ethers, ethoxylated isooctyl,- octyl- or nonylphenol~ alkylphenol polyglycol ether~, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated cas~or oil, polyoxyethylene alkyl ethers or polyoxypropylene, lauryl alcohol polyglycol ether acetate, sorbitol esters, ligninsulfite waste liquors or methylcellulose.
Powders, broadcasting agents and dusting agents can be prepared by mixing or milling the active sub-stances together with a solid carrier.
Granules, for example coa~ed, Lmpregnated and homogeneous granules, can be prepared by binding the active ingredients to solid carriers. Solid carriers are mineral earth~, such as silica gel, silicas, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, kie~elguhr, calcium sulfate, magnesium sulfate, magnesium oxide, milled plastics, fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate and urea3, and vegetable products, such as grain flours, bark meal, wood meal and nutshell meal, cellulosic powders and other solid carrier~.
~he formulations contain from 0.1 to 95, prefer-ably from 0.5 to 90, % by weight of the active in-gredients. The active ingredients are used in a purity of from 90 to lO0~, preferably from 95 to 100% (according to the NMR spectrum).
~he growth regulators or the active ingredients O . Z . 0050/41834 can be applied by the preemergence or postemergence method. If the active ingredients are less well tolerated by certain crops, it i~ pos~ible to use application methods in which the herb.icides are sprayed 5 with the aid of sprayers in such a way that as far as poss.ible they do not come into contact with the leaves of the sensitive crops while the active ingredients reach the leaves of undesirable plant~ g:rowing underneath or the uncovered soil surface ~post-directed, lay by).
The application rates of active ingredient mixture are from 0.01 ~ 0.01 to 2 ~ 0.001, preferably front 0 . 03 + O . 02 to 1 + O . 001, kq/ha of active substance (a.s.), depending on the s~a~on, target plants and stage of grow~h.
The synergistic mixtures can influence virtually all ~tage3 of development of a plant in di~ferent ways and are therefoxe used a~ growth regulators. The range of activity of the plant growth regulators depend~ in particular a) c7}1 the plant ~pecies and variety, b) on the time of application~ ba~ed on the stage of development o~ tha plant, and on the ~ea~on, r) on the place and method of application (for example s~ed dre~ing, ~oil treatment, foliage application or trunk in~ection in .he case of trees), d) on climatic ~actors, eg. temperature, amount of _ precipitation and also length of day and light inten~ity, e) on the soil quality ~including fertilizer applica-tion), f) on the formulation or application form of the active ingredient and finally g) on the ~oncen~rations in which ~he active substance is used.
From ~he various possibl.a applications of the novel agents in cultivation, in agriculture and in hortictllture, ~ome are mentioned below.
- 15 - o.Z. 0050/~1834 A. The vegetative growth of the plant~ can be greatly inhibited with the compounds which can be used according to the invention, this being manifested in paxkicular in a reduction in the growth in length. The treated plants accordingly h ve a stunked growth; more-ov~r, a darker leaf coloration is ob~erved.
Reduce~ intensity of growth of yrasses along road edges, hedges and canal banks and on lawn area~, such as parks, sports grounds, orchards, ornamenkal lawn~ and airfield~, proves advantageous in practice, enabling the labor-inten~ive and expensive cutting of lawns to be rsduced.
The increase in the strength of crop~ su~c~ptible to lodging, such a~ cereals, corn, sunflowers and soy-bean, is also of economic interest. The re~;ultingshortening and strengthening of the stem reduce or slLminate the danger of lodging (of bending) of plants - under unfavorable weather conditions prior to harvesting.
The u~e of growth regulator~ for inhibiting the growkh in length and for changing $he tLme of ripening of ootton iB also importan~. This permit~ completely mechanized harvesting of thi~ important crop.
In the ca3a of fruit tree~ and other trees, the growth r~gulators permit a reduction in cutting cost~.
~oreover, the alternance of fruit trees can be broken by growth ragulators.
The lateral branching of the plants can also be increased or inhibited by the u~e of grow~h regulators.
Thi~ is of interest if, for example, in the case of tobacco plants, it i~ intended to inhibit the formation of ~ide ~hoot~ in favor of leaf growth.
The ~rost rasi~tanco can also be considerably lncrea ed with growth regulator3, for example in wintar rape. On the one hand, the growth in length and the development of a leaf or plant mas~ which i3 too luxuri-ant (and hence particularly su~ceptible to fro3t) are inhibited. On the other hand, the young rape plants are 16 - O.Z. OOS0/41834 held back in the vegetative stage of development after sowing and before the onset of the winter frosts~ in spite of favorable growth conditionst This also elLmina tes the danger of fro~t to plants which tend to ~xhibit a premature decline in ~he inhibition of blooming and to go over into the genPrative phase. In other crops too, for sxamplP winter cereals, it is advantageous if the stocks are well tillered in the fall as a result of treatment ~ith novel compounds bul: do no~ en~er thP
winter with too luxllriant a growt.h. This makes it possible to avoid high sensitiYity to frost and, owing to the relatively small leaf or plant mass, attack by various diseasP~ ~ fox example fungal disease). Inhibi tion of the vegetative growth furthermore permits denser planting of the soil in the case of many cxop~, making it possible to achieve a greater yiel , ba~ed on soi:L area.
. The growth regulators make it possible to achieve greater yield both of plant part~ and of plant in-gredient~. For example, it i~ po ~ible to induce the grow~h of laxger amounts o bud~, blooms, leaYes, fruits, seeds, roots and tuber~, to increase the content of sugar in sugar beet~, sugar cane and citru~ fruits, to increase . the protein content of cereal~ or soybean or to stLmulate greater lat~x flux in rubbsr tree~.
By intervening in the plant metaboli~m or by prcmoting or inhibiting vegetative and/or generative growth, -the synergistic agents can result in increased yield~, C. Finally, both shortening or lengthening of the 8taga9 of development and acceleration or re~ardation o~
the ripening of the haxvested plant parts bsfore or after harve~ing can be achLeved with plant growth regula~or~.
For example, it is of economic interest to facilita~e harve~ting, thi~ being pe~litted by con-centrated dropping or reduction in ~the adhesion to the tree in the ca~e of citrus fruit~, olive~ or other specie~ and varieties ~f pomes, drupes and hardshall ;
- 17 ~ O.Z. 0050/~1834 fruit. The same m~chanism, ie. promotion of the forma-tion of absci~sion tissue between the fruit or leaf part and the sprout part of the plant is also essential for readily controllable defoliation of crops such as for example cotton.
D. Furthermore, the water consumption of plants c~n be reduced with growth regulators. This is particularly important for agricultural areas which have to be artifi-cially irrigated at great expense, for example in arid or semiarid regions. By using the novel ~ubstances, it is po~sible to reduce the intensity of irriga~ion and hence to carry out more economical farming. Under the influ-ence of growth regulators, the available water is bet~er utilized becau~e, in~er alia, 15 - ~he extent of opening of the stomata is re~uced, - a thicker epidermi~ and cuticula are formed, - root penetration o~ the soil i~ improved and - the microclLmate in the crop is advantageou~ly affected by more compacted growth.
The novel synergis~ic agents c~n be fed to the crops both via the seed ~as seed dre~sings) and via the soil, ie. through the root and, particularly preferably, via the foliage by spraying.
Because of the good toleration by plants, the application rate can ba greatly varied.
In view of the wide range of applica~ion methods, the novel agents can be used in cere 1 crops and cotton.
The synergi~tic effect can be determined by the formula of S.R. Colby (Wa~ds 15 (1967), 20~2) E = X ~ Y - X Y / 100 where the variables have th~ following meanings:
X 18 the ~ea~urable effect of the active ingredient I at an applica~ion .ra~e ~a], ; Y is the mea8urable efEect of the active ingredient II at an appl~cation rate ~b] and is the expected measurable efect of a mixture of active ingredient I at the application rate ~a] and of j;, , ! , ~;, . ..
- 18 ~- O.Z. 0050/41834 active ingredient II at the application rate ~b].
From the difference between the expected v~lue ~
according to Colby and the measured value, it is possible ~o determine whether there is a synergistic efect (reinforcement of the effect ox increase of activity) or an antagonistic effect (weakening of the effect or reduction in activity), or if there are merely additive effec~s on the activity, this being the case if the two values correspond.
The Lmproved biological action of the mixtures compared with the individual substances in cereal crops and cotton can be demonstrated in field trials.
Various mix~ures of th~ following compouncls were inves~igat~d:
A
N~N,N~Trimethyl-N-~-chloroethylammoniumchloride(chloro-mequat chloride) N,N-DLmethylpiperidinium chloride ~mepiquat chloride) C
2-~4-Isopropyl-4-methyl-5-oxo-2-imidazolin 2-yl)-3-quinolinecarbo~ylic acid (imazaquin) D
I~opropylammonium 2-(4-isopropyl-4-methyl-S-oxo-2-imidazolin-2~yl)~3-nicotinecarboxylate (imaæapyr) : E
5-Ethyl 2-(4-isopropyl-4-methyl 5-oxo-2-imidazolin 2 yl)-3 nicotinecarbo~ylic acid (imazethapyr) ~he trial~ were carried out on plots, each measuring 12.5 m2 (cereals) or 50 m2 (cotton), with 4 replicates in each ca~e. Cultivation, ~ertilizer ap-plication and the use of crop protection agent~ again~t growth of weeds and attack by fungi and by in~ect pes~s were carried out in a manner conventional ~or t~le location.
The novel agent~ were applied by the post-emergence method (3.5 bar, 400 l/ha of water).
~ '` l"`1 r r - 19 - - Z ~ 0(~50/41~33 The ~bovemPntioned cexeal trial~ show that the novel mixtures are clearly superior to the known mixture A ~ C (EP-A-149 083). Furthenmore, Ta~le 2 shows that a mixture consisting of two diferent quaternary ammonium compounds with a triazole has an action superior to that of ~he known combination of A + C.
TABL~ 1 Crop: Winter barley (variety: Marinka) Type of soil: Clayey loam Sowing: Saptember 28, 1988 Treatment: March 28, 1989 Evaluation: Plant damage Nay 12, 1989 Height of growth May 17, 1989 Sub~tance g/ha of Plant Height of grow~h active damage cmDif~erence rom ingredient % control ~ (cm)_ Control - 0 102.1 A 690 0 101.60.5 D 10 5 72.5- 29.6 A + D 6gO ~ 5 6 71.9 - 30.2 A + D 690 ~ 10 6 57 4 6 - 44.5 A + D 690 ~ 20 11 41.4- 60.7 A ~ C 759 ~ 16.5 3 84.0- 18.1 ~ ~ C 1150 + 25 10 78.9- 23.2 - 20 - OOZ~ 0050/4183 Crop: Winter wheat (variety Baroudeur) Type of soil: Clayey sand Sowing: October 2, 1989 Txeatm~nt: March 28, 1990 Evaluation: Plant damage May 17, 1990 Height of growth June 5 t 1990 Substance g/ha of Plant Height of growth active damage cm Difference from ingredient % control ~ . (cm) Control 0 0 108.0 A + E 920 + 1 0 100.8 - 7.2 A + E 920 t 2 0 99O2 - 8.8 A + E 920 ~ 4 0 99.8 - 8.2 ?
A ~ B ~ E 690 + 230 ~ 20 100.5 - 7.5 A + C 920 + 2 0 101.0 7.0 T~BLE 3 Crop: Winter wheat (varietyO ~axoudeur) ~ype of ~oil: Sandy loam Sowing: October 12, 1989 Treatment: March 5, 1990 Evaluation: Plant da~age June 6, 1990 : Internodal length Ju~e 6, 1990 Ear length June 6, 1990 Substance g/ha o Plant Internodal length Ear length active damage cm Dif~erence cm Difference ingredient ~ fxom con~rol From control cm cm ~
Control 0 a 5.2 8.4 A ~ C 920 -~ 2 0 3.B - 1.4 8.3 ~.l A -~ E 920 ~ 2 0 3.5 - 1.7 8.5 +0,1 . . :
:., -. , , ~ . '' :` :
- 21 - O.Z. 0050/41834 Crop: Winter wheat (variety: Baroudeur3 Type of soil: Sandy loam Sowing: October ~, 1989 Treatments March 1, 1990 Evaluatîons Plant damage May 10, 1990 Height of yrowth May 10, 1990 Substance g/ha of Plant Height of growth active damage cm Difference from 13 ingredient ~ con~rol ~cm) Control 0 0 96.7 A ~ C 920 + 2 0 ~7.6 ~ 9.1 : 15 A + E 920 ~ 1 0 86O2 ~ 10.5 A + E 920 ~ 4 0 86.9 - 9.8 _ , - 22 - O. 2 . 0050/4183 Crop . Winter wheat ( vari ty: Rraka Type of soil: Loamy sand Sowing : November 7, 1 9 8 9 Treatment: April 2, 1990 ~valuation: Plant damage June 6, 1990 Height of growth June 6, 1990 Substance g/ha of Plant Height of growth active damage cm Diffç?rence from ingredien~ % control ( cm Control 0 0 117 . 0 B 690 0 107 . 0 - 10 . 0 1~ C 5 0 11~.5 ~ 1.5 B ~ C 690 + 2 . 5 0 lG6 .1 -10 . 9 A + C 690 ~ 15 0 106 . 9 - 10 .1 EXANPI.ES 6 AND 7 The ~ynergistic e~fect of ~he mixture A + D is demon~trated using barley. It is noted that the addition oiE > 10 g/ha of active ingredient o~ ~ubstance D can lead to plant damage.
.
' ' , - 23 - O.Z. 0050/41834 Crop: Su~mer barley (variety: Gimpel) Type of ~oil: Clay Sowing: March 20, 1989 Treatment: May 18, 1989 Evaluation: Plant damage June 2, 1989 Height of growth Juns 12~ 1989 Substance g/ha of Plant Height of growth active damage cm Difference from ingredient % control ~cm) Control 0 0 101.2 A 690 0 9fi.9 ~ 4,3 D 10 5 55.6 - 45.6 A ~ D 6~0 ~ 5 7 44.6 ~ 56.6 A ~ D690 ^~ 10 8 42.9 - 58.3 A + D690 t 20 8 42.5 - 58.7 TABL~ 7 : 20 Crops Winter barley (variety: Igri) Type of soil: Very clayey loam Sowingo September 22, 1988 Trea~ment: Rpril 21, 1990 Evalllation: Plant dama~e May 15, 1989 : 25 Height of g~owth MAY 22, 1989 Substance g/ha of Plant Height of growth _ active damage cm Difference from ingredien~ % control (cm) .... ~
Control 0 0 111O2 ~90 0 111.2 0 D 10 12 82.0 - 29.2 A + D 690 ~ 10 21 71.2 - 40.0 A ~ D 690 -~ 20 54 63.8 - 47.4 _ ~4 ~ 0.2. 0050/41~34 ~XAMPLES 8 TO 10 In the case of wheat and barley, the mixture A -~
E also leads to synergistic shortening of the stem, im-proved strength and correspondingly greater yields.
Crop: Summer wheat (variety: Ralle) T~pe of soil: Clay Sowing: March 20, 1989 Tre~tmen~. May 18, 1989 Evaluation: Plan~ damage June ~, 1989 Height of growth June 130 1989 Substance g/ha of Plant Height of growth active damage cm Differ~:nce from ingredient ~ control (cm) Control 0 0 7g.8 A 690 0 63.0 - 16.8 E 10 0 7~.8 - 1.0 A + E 690 ~ 5 0 50~1 - 19.7 A + E69~ ~ 10 0 57.8 - 22.0 E690 + 20 4 56.0 - 23.8 TABL~ 9 Crop: Summer wheat (variety$ Ralle) Type of soil: Loam~ ~and Sowing~ February 21, 1989 Tre~ment: ~ay 12, 1989 Evaluation: Plant damage Jun~ 21, 1989 Height of growth Augu~t 3, 1989 Substanca g/ha of Plant Height o~ gxowth active damage cm Differerlce from ingred.ient % control ~cm) Control0 0 36.2 6~ 0 36.8 ~ 0.~
E 10 0 3~.5 - 1.7 '' ' .
.
- 25 - O.Z. 0050/41834 A + E 690 ~ 10 0 39O1 + 2.9 Crop: Winter barley (varietyo Igri~
Type of soil: Very clayey loam Sowing: September 22, 1989 Treatment/ April 21, 1989 Evaluation: Plant damage May 15, 1989 Lodging July 5, 1989 Grain yield 3uly 11, 198g 10 Substance g/ha of Plant Lodging/ Grai~ yield/
active damage difference ~iff~rence ingreclient from control frc~ con~l % ~%] [%]
. . .
Control0 0 46 75.5 690 0 48 + 2 69.7 5.8 0 ~ + ~ 69.3 - 6.2 A + E690 + 10 0 34- 12 76.9 ~ 1.4 A + E690 + 20 0 3610 76.2 ~ 0.7 Mixkures consisting of compounds B + C lead to a synergistic inhibition of growth in barley, whsat and cotton. The resulting improved strength is illu~trated by Exampl~ 13.
- 26 - 0.~. OGSO/41834 TABLE ll Crop: Summer wheat (variety Ralle) Type of ~oil: Clay Sowing: March 20, 1989 Treatment: May 19, 1989 Evaluation: Plant damage June 22, 1989 Height of growth June 13, 1989 Substance g/ha ofPlant Height of growth activedamage cm Difference from ingredient ~ co~trol (cm) .. _ . . ~
ControlO 0 80.6 B 690 0 66.0 ~ 14.6 C 10 0 ~l.O + 0.4 : ~ ~ C690 + lO O 61.5 - 19.1 B + C690 + 20 7 49~8 - 30.8 ~ABL~ 12 Crops Winter wheat (variety: Kraka) Type of soil: Loamy sand Sowing: November 7, 1989 Tr~atment: April 30, 1990 . Evaluation- PLant damage June 5, 1990 Heigh~ of growth June 5, 1990 Substance g~ha ofPlant Haight of growth active damage cm Diff~rence from _ ingredient ~ control (cm) Control O 0 9S.1 B 690 0 86.0 - 9.}
C 5 0 95.4 ~ 0.3 B + C 690 ~ 1.25 0 80.3 - 14.8 B + C 6gO ~ 2.5 0 84.0 - 11.1 B + C 690 + 5.0 0 84.5 - 10.6 ,, .
- 27 - O.Z. 005~/41834 Crop: Summer barley ( varie-ty O Gimpel ) Type of soil: Clay Sowing O Marc h 2 0, 1 9 8 9 Treatment: May 18, 19 8 9 Evalua~ion: Plant damage June 2, 198 Height of growth :rune 12, 198 Lodging July 2 4, 19 8 9 Sub~tance g/ha of Pla.nt Height o:E Lodging~
active damage growth~ dif ference ingredient ~ difference from control from control [cm]
[cm]
Control 0 0 95 . 4 38 B 690 0 94 . 4 -1 G 0 4g + 11 C 10 0 91 O 0 -4 . 4 ~0 ~ 2 B + C 690 + 5 0 82 . 2 -13 . 2 0 - 38 B ~ C 690 + 10 14 61. 6 -33 . 8 0 - 38 B + C 690 ~ ~0 14 S4 ~ 8 -40 . 6 0 - 38 Crop: Cotton (variety: SJ - 2 ) Type o~ soll s Sandy loa~
Sowing: ~ebruary 24, 1989 25 Treatmen$ - June 2~, 198g Evaluations Plant damagl3 July 6, 1989 Heiçrht of growth October 5, 1989 Sub~tance ~/ha of Plant Height of growkh active damage cm Difference from ingredient ~ control ~cm]
Control 0 0 125 . 0 B 30 0 116 . 2 -8 . 8 C 10 0 12~.2 ~1.2 B+ C 30 ~ 5 0 ill . 2 -13 . 8 B~ C 30 ~10 0 110 . 5 -14 . 5 13+ (~ 30 ~~0 0 107 . 5 -17 . 5 ,.i j .,,, ,1,.
- 28 - O.Z. 0050/~1834 CropO Cotton (variety- Stoneville sa5 ) Type of soil: Sandy loam Sowing: May 26, 1989 Treatment: July 24, 1989 Evaluation: Plant damage July 31, 1989 Substance g~ha of Plant Height of growth active damage cm Differ~nce from ingredient % control [cm]
Control 0 0 121.2 B 60 0 111.0 - 10.2 ~ 10 0 122.8 + 1.6 B ~ C 60 + 5 0 112.5 - 8.7 B ~ C 6Q + 10 0 lOg.8 - 11.4 B ~ C 60 + 20 0 107~5 - 13.7 Mixture~ o substances B + ~ also lead to a æmaller plant height and grea~er yield~ in the case of barley, wheat and cotton.
~ Crop: Summer wheat (variety: Ralle) .~ Type of soil 5 Loamy sand Sowing: Augus~ 15, 1989 Z5 ~reatment: August 15, 1989 Evaluations Plant damage June 2, 1989 ~Ieight of growth A~gust 3, 1989 Sub~tance g/ha of Plant Hsiyht of growth active dama~e cm Dif~erence from ingredient % control [cm]
Control 0 0 38.0 B 690 0 40.5 -~ 2.5 D 10 0 38.4 + 0.4 B -~ D690 + 5 0 44.6 + 6.6 B -~ D690 -~ ln 0 40.1 + 2.1 B + D690 t 20 5 31.0 - 7.0 I `' ` ~ "' . ' ! .
- 29 - O.Z. 0050/41834 Crop: Summer barley (~ariety: GLmpel) ~ype of soil: Clay Sowing: March 20, 1989 Treatment May 18, 19 8 9 Evaluation: Plant damag~ June 2, 1989 Heigh~ of grow~h June 12, 1989 Substance g/ha of Plant Height of growth active dam~ge cmDifference from ingredient % control ~cm]
Control 0 0 g5.4 B 690 0 94.4 - 1.0 D 10 5 51.8 - 43.6 B + D 690 -~ 10 0 43.9 - 51.5 B + D 690 + 20 6 43.5 51.9 TABL~ 18 Crop: Cotton (variety~ ~C - 510) Type of soil: Loam Sowing^ ~ebruary 28, 1989 Treatment: June 27, 1989 Evaluation: Plant damage July 6, 1989 Height of growth July 26, 1989 Substance g/ha of Plant Height o~ grow~h ac~ivQ damage cmDifference from ingredient % control [cm]
Control 0 0 g6.6 B 30 0 88.7 - 7.g D 10 6 96.6 0 B ~ D 30 ~ 5 3 a4 . 1- 12 ~ 5 B ~ D 30 ~ 10 6 83.4 - 13.2 B -~ D 30 ~ 20 8 80.8 - 15.8 EXAML~LES 19 TO 25 In tha ca~e of baxlsy, oat~, wheat and cotton, it wa~ al~o possible to reduce the height of growth, reduca lodging and increa3e the yield by mixturQs of substances :~ Y'1 - 30 - O.Z. 0050/41834 B ~ E.
TABLE lg Crop~ Summer wheat (variety: Ralle) Type of soil: Clay Sowing: March 20, 1989 Treatment: May 19, 1989 Evaluation: Plant damage June 2, 1989 Height of growth June 13, 1989 Sub~tance g/ha of Plant Height of grow*h active damage cmDiffer~nce from ingredient % control [cm]
Contxol 0 0 80.6 B 690 0 66.0- 14.5 E 10 a 8~oO+ 1.4 B ~ E690 ~ 5 9 60.0- 20.6 ; B + E690 * 10 0 57.023.6 690 + ~0 5 54.0~ 26.6 TA~LE 20 -~ 20 Crop: Winter wheat ~variQtys Xanzler) ~ype of soil: Clay Sowing: ~ctober 4, 1989 : Treatment: April 5, 1990 E~aluation: Plant damage June 5, 1990 Height of growth June 5; 1990 Sub~tanc~ g/ha of Plant Haight of gr~wt;h active damage cm Di~ference frvm inyredient % control [cm]
Control 0 0 122.9 B 690 0 117.2 - 5.7 E 5 0 122.8 - 0.1 B + ~ 690 + 1.25 0 113.2 - 9.7 B + ~ 690 t 2.5 0 114.8 ~ 8.1 B ~ 90 t 5 0 113.4 - 9.5 , - '' ~ ' :
~ ~ .
- 31 - O.Z. 005~/4183 Crop: Winter wheat (variety: Kraka) Type of soil: Loamy sand 50wing: November 7, 1989 Treatment: May 2, 1990 Evaluation: Plant damage June 5, 1990 Height of growth June 5, 1990 Substa~ce g/ha o~ Plant Height of grow*h active damage cm Difference fro~
lD ingredient % con~rol ~cm]
Control a 0 97.9 B 690 0 88.7 - 9.2 E 5 0 ~9.1 ~ 1.2 B ~ E 690 ~ 2.5 0 86.0 - 11,.9 B ~ E 690 -t 5 0 85.4 12.5 TAB~E 22 Crop: Oats (variety. Fl~mingsnova) Type of soil: Sandy lo~m Sowing. March R, 1990 Trea~ment: May 131 1990 : Evaluation: Plant damage June 8, 1990 . Height of growth June 8~ 1990 ; Sub~tance g/ha of Plant Height of growth active damage cm DifferQnce from ingredient % control [cm]
Control0 0 97.5 B 690 0 91.9 - 5.6 E 5 0 95.8 ~ 1.7 B + E690 + 5 0 89.1 - 8.4 - 32 - O. Z . 0050/41834 Crop: Summer barley ( variety: Gimpel ) I~ype of soil: Clay Sowing: March 20~ 1989 Treatment: May 18, 19 8 9 Evall~ation~ Plant damage June 2, 1989 Height of growth June 12, 1989 Lodging J uly 2 4, 1 9 8 9 Substance g/ha of Plant Height of Lodging/
active damage growt:h/ dif feren~e ingredient % difference from con f rom control trol [ % ]
[cm]
Control 0 0 95 . 4 38 B 690 0 94 . 4 - 1. 0 49 ~ 11 E 10 0 93.1 - 2.3 42 +4 E~ ~ E 690 ~ 10 0 91. 6 -3 . 8 36 - 2 B ~ E ~9û ~ 20 6 67 . 5 -27 . 9 0 - 38 2 û TAB~l~ 2 4 Crop s Cottoll ( variety: S~ - 2 ) Type of ~oil: Sandy loam Sowing : Fe~ruary 2 4, 1 9 8 9 I'reatment o June 2 7, 19 8 9 . ~ 25 Evaluation: Plant dsmage July 6, 198~
HQight of growth October 5, 1989 Sub~tance g/ha of Plant Height of grow~h ac:tive damage cm Di~erence from ing-redient % control ~cm]
3 0 ~
Control 0 0 125 . 0 B 30 0 116.2 8.8 2 130 . 0 + 5 . 0 B -1 E 30 + 5 0 111. 2 13 . 8 3S B ~ E 30 ~ 10 ~ 111. 2 -13 . 8 ~ 1 - 33 -O.Z. 0050/41~34 Crop~ Cot~on (variety: GC - 510) Type of soil: Loam Sowing~ February 28, l9B9 Treatment: June 27, 1989 Evaluation: Plant damage June 6~ 1990 Yield of seed cotton June 6, 1990 Sub~tance g/ha of PlantYield of seed co~ton active damagekg/ha Difference ~rom ingredient ~ control (kg/ha) :
Con~rol 0 0 3233 B 30 0 3375 + 142 30 + 5 ~ 3~53 + 22~
B + E 30 ~ 10 4 4003 ~ 770 B ~ E 30 + 20 3 2693 ~ 540
Claims (11)
1. A plant growth regulator containing a synergistic mixture of one or more growth regulating quaternary ammonium salts from the group consisting of the compounds I, comprising N,N-dimethylazacycloheptanium salts, N,N-dimethylpiperidinium salts, N,N-dimethyltetrahydro-pyridazinium salts, N,N,N-trimethyl-N-2-chloroethyl-ammonium salts, N-methylpyridinium salts and N,N-dime-thylpyrrolidinium salts, and an imidazolinyl derivative of the general formula II
II
where R1 is C1-C4-alkyl, R2 is C1-C4-alkyl or C3-C6-cyclo alkyl, R3 is hydrogen, hydroxyl, C1-C12-alkyl, C1-Cl2-alkoxy, C1-C12-alkylamino, di-C1-C12-alkylamino or is phenyl, phenoxy or phenylamino, where the aromatic radicals may carry from one to five halogen atoms and/or from one to three of tha following groups: C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio or C1-C4-haloalkylthio, R4 is hydrogen, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio or C1-C4-haloalkylthio and R5 and R6 independently of one another are each one of the groups stated for R4 or together form a 1,3-butadiene 1,4-diyl group which may carry from one to four halogen atoms and/or from one to three of the following groups: C1-C4-alkyl, C1-C4-haloalkyl, C1-C4 alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio or C1-C4-haloalkylthio, and inert additives.
II
where R1 is C1-C4-alkyl, R2 is C1-C4-alkyl or C3-C6-cyclo alkyl, R3 is hydrogen, hydroxyl, C1-C12-alkyl, C1-Cl2-alkoxy, C1-C12-alkylamino, di-C1-C12-alkylamino or is phenyl, phenoxy or phenylamino, where the aromatic radicals may carry from one to five halogen atoms and/or from one to three of tha following groups: C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio or C1-C4-haloalkylthio, R4 is hydrogen, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio or C1-C4-haloalkylthio and R5 and R6 independently of one another are each one of the groups stated for R4 or together form a 1,3-butadiene 1,4-diyl group which may carry from one to four halogen atoms and/or from one to three of the following groups: C1-C4-alkyl, C1-C4-haloalkyl, C1-C4 alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio or C1-C4-haloalkylthio, and inert additives.
2. A plant growth regulator as claimed in claim 1, containing one or more growth-regulating quaternary ammonium salts from the group consisting of the compounds I, comprising N,N-dimethylpiperidinium salts and N,N,N-trimethyl-N-2-chloroethylammonium salts.
3. A plant growth regulator as claimed in claim 1, - 35 - 0.Z. 0050/41834 containing an imidazolinyl derivative of the formula II
as claimed in claim 1, where R1, R2, R4, R5 and R6 have the meanings stated in claim 1 and R3 is hydrogen, hydroxyl, C1-C8-alkyl, C1-C8-alkoxy, C1-C8-alkylamino or di-C1-C8-alkylamino or is phenyl, phenoxy or phenylamino, where the aromatic radicals may carry from one to five halogen atoms and/or from one to three of the following groups:
C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-halo-alkoxy, C1-C4-alkylthio or C1-C4-haloalkylthio, and inert additives.
as claimed in claim 1, where R1, R2, R4, R5 and R6 have the meanings stated in claim 1 and R3 is hydrogen, hydroxyl, C1-C8-alkyl, C1-C8-alkoxy, C1-C8-alkylamino or di-C1-C8-alkylamino or is phenyl, phenoxy or phenylamino, where the aromatic radicals may carry from one to five halogen atoms and/or from one to three of the following groups:
C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-halo-alkoxy, C1-C4-alkylthio or C1-C4-haloalkylthio, and inert additives.
4. A plant growth regulator as claimed in claim 1, containing a synergistic mixture of one or more growth-regulating quaternary ammonium salts from the group consisting of the compounds I, comprising N,N-dimethyl-piperidinium salts and N,N,N-trimethyl-N-2-chloroethyl-ammonium salts and an imidazolinyl derivative of the formula II as claimed in claim 1, where R1 and R2 have the meanings stated in claim 1 and R3 is hydrogen, hydroxyl, C1-C8-alkyl, C1-C8-alkoxy, C1-C8-alkylamino or di-C1-C8-alkylamino or is phenyl, phenoxy or phenylamino, where the aromatic radicals may carry from one to five halogen atoms and/or from one to three of the following groups:
C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-halo-alkoxy, C1-C4-alkylthio or C1-C4-haloalkylthio, R4 is hydrogen or halogen and R5 and R6 independently of one another are each hydrogen, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy; C1-C4-haloalkoxy, C1-C4-alkylthio or C1-C4-haloalkylthio, or together form a 1,3-butadiene-1,4-diyl group which may carry from one to four halogen atoms and/or one of the following groups: C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio or C1-C4-haloalkylthio, and inert additives.
C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-halo-alkoxy, C1-C4-alkylthio or C1-C4-haloalkylthio, R4 is hydrogen or halogen and R5 and R6 independently of one another are each hydrogen, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy; C1-C4-haloalkoxy, C1-C4-alkylthio or C1-C4-haloalkylthio, or together form a 1,3-butadiene-1,4-diyl group which may carry from one to four halogen atoms and/or one of the following groups: C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio or C1-C4-haloalkylthio, and inert additives.
5. An agent as claimed in claim 4, containing a synergistic mixture of N,N-dimethylpiperidinium chloride, N,N,N-trimethyl-N-2-chloroethylamnonium chloride and 5-ethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-3-nicotinecarboxylic acid.
- 36 - O.Z. 0050/41834
- 36 - O.Z. 0050/41834
6. A plant growth regulator as claimed in claim 1, containing a synergistic mixture of N,N-dimethyl-piperidinium chloride and 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-3-quinolinecarboxylic acid and inert additives.
7. A plant growth regulator as claimed in claim 1, containing a synergistic mixture of N,N-dimethyl-piperidinium chloride and isopropylammonium 2-(4-isoprop-yl-4-methyl-5-oxo-2-imidazolin-2-yl)-3-nicotinecarbox-ylate and inert additives.
8. A plant growth regulator as claimed in claim 1, centaining a synergistic mixture of N,N-dimethyl-piperidinium chloride and 5-ethyl-2-(4-isopropyl-4-methyl 5-oxo-2 imidazolin-2-yl)-3-nicotinecarboxylic acid and inert additives.
9. An agent as claimed in claim 1 or 2 or 3 or 4 or 5 or 6 or 7 or 8, wherein tha weight ratio of ammonium salt I to imidazoline derivative II is from 0.1 : 1 to 1000 : 1.
10. A method for regulating plant growth, wherein the plants, their habitat or their seeds is or are treated with an amount, having a regulating effect, of a syner-gistic mixture as claimed in claim 1 or 2 or 3 or 4 or 5 or 6 or 7 or 8 or 9.
11. A method as claimed in claim 10, wherein the plants are cereals or cotton.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4026530A DE4026530A1 (en) | 1990-08-22 | 1990-08-22 | SYNERGISTIC AGENTS FOR REGULATING PLANT GROWTH |
| DEP4026530.7 | 1990-08-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2048275A1 true CA2048275A1 (en) | 1992-02-23 |
Family
ID=6412682
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002048275A Abandoned CA2048275A1 (en) | 1990-08-22 | 1991-08-01 | Synergistic agents for regulating plant growth |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0472091B1 (en) |
| JP (1) | JPH05124915A (en) |
| KR (1) | KR920003857A (en) |
| CN (1) | CN1059633A (en) |
| AU (1) | AU8260891A (en) |
| CA (1) | CA2048275A1 (en) |
| CS (1) | CS248891A3 (en) |
| DE (2) | DE4026530A1 (en) |
| DK (1) | DK0472091T3 (en) |
| ES (1) | ES2064833T3 (en) |
| HU (1) | HU206433B (en) |
| PL (1) | PL167128B1 (en) |
| RU (1) | RU2050136C1 (en) |
| UA (1) | UA26391A (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100074949A1 (en) | 2008-08-13 | 2010-03-25 | William Rowe | Pharmaceutical composition and administration thereof |
| US8354427B2 (en) | 2004-06-24 | 2013-01-15 | Vertex Pharmaceutical Incorporated | Modulators of ATP-binding cassette transporters |
| NZ587551A (en) | 2004-06-24 | 2012-01-12 | Vertex Pharma | 5-Amino-phenol derivatives such as 5-amino-2,4-di-tert-butyl-phenol |
| PL3219705T3 (en) | 2005-12-28 | 2020-08-10 | Vertex Pharmaceuticals Incorporated | Pharmaceutical compositions of the amorphous form of n-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide |
| AU2010204310B2 (en) * | 2009-01-07 | 2014-07-24 | Basf Se | Pesticidal mixtures |
| KR101852173B1 (en) | 2009-03-20 | 2018-04-27 | 버텍스 파마슈티칼스 인코포레이티드 | Process for making modulators of cystic fibrosis transmembrane conductance regulator |
| US8802700B2 (en) | 2010-12-10 | 2014-08-12 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-Binding Cassette transporters |
| CN109966264A (en) | 2012-02-27 | 2019-07-05 | 沃泰克斯药物股份有限公司 | Pharmaceutical composition and its application |
| US9701639B2 (en) | 2014-10-07 | 2017-07-11 | Vertex Pharmaceuticals Incorporated | Co-crystals of modulators of cystic fibrosis transmembrane conductance regulator |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE795534A (en) * | 1972-02-18 | 1973-08-16 | Basf Ag | AGENTS FOR REGULATING PLANT GROWTH, CONTAINING NITROGEN SALT AS ACTIVE INGREDIENT |
| US4509973A (en) * | 1984-01-13 | 1985-04-09 | American Cyanamid Company | Plant growth regulating compositions |
| ZA86707B (en) * | 1985-02-04 | 1986-09-24 | American Cyanamid Co | Turfgrass management compositions |
-
1990
- 1990-08-22 DE DE4026530A patent/DE4026530A1/en not_active Withdrawn
-
1991
- 1991-08-01 CA CA002048275A patent/CA2048275A1/en not_active Abandoned
- 1991-08-12 CS CS912488A patent/CS248891A3/en unknown
- 1991-08-13 DK DK91113554.9T patent/DK0472091T3/en active
- 1991-08-13 EP EP91113554A patent/EP0472091B1/en not_active Expired - Lifetime
- 1991-08-13 ES ES91113554T patent/ES2064833T3/en not_active Expired - Lifetime
- 1991-08-13 DE DE59103571T patent/DE59103571D1/en not_active Expired - Lifetime
- 1991-08-19 JP JP3206675A patent/JPH05124915A/en not_active Withdrawn
- 1991-08-21 AU AU82608/91A patent/AU8260891A/en not_active Abandoned
- 1991-08-21 UA UA5001325A patent/UA26391A/en unknown
- 1991-08-21 KR KR1019910014399A patent/KR920003857A/en not_active Application Discontinuation
- 1991-08-21 RU SU915001325A patent/RU2050136C1/en not_active IP Right Cessation
- 1991-08-21 HU HU912757A patent/HU206433B/en not_active IP Right Cessation
- 1991-08-21 PL PL91291484A patent/PL167128B1/en not_active IP Right Cessation
- 1991-08-22 CN CN91105922A patent/CN1059633A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE59103571D1 (en) | 1995-01-05 |
| CS248891A3 (en) | 1992-03-18 |
| KR920003857A (en) | 1992-03-27 |
| CN1059633A (en) | 1992-03-25 |
| HU912757D0 (en) | 1992-01-28 |
| RU2050136C1 (en) | 1995-12-20 |
| DE4026530A1 (en) | 1992-02-27 |
| DK0472091T3 (en) | 1995-03-13 |
| PL291484A1 (en) | 1992-08-10 |
| HUT58462A (en) | 1992-03-30 |
| JPH05124915A (en) | 1993-05-21 |
| ES2064833T3 (en) | 1995-02-01 |
| EP0472091B1 (en) | 1994-11-23 |
| EP0472091A1 (en) | 1992-02-26 |
| AU8260891A (en) | 1992-02-27 |
| UA26391A (en) | 1999-08-30 |
| PL167128B1 (en) | 1995-07-31 |
| HU206433B (en) | 1992-11-30 |
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