Plant protecting and regulating compositions – Plant growth regulating compositions – Plural active ingredients
Reexamination Certificate
1999-12-03
2001-05-01
Clardy, S. Mark (Department: 1616)
Plant protecting and regulating compositions
Plant growth regulating compositions
Plural active ingredients
C504S286000
Reexamination Certificate
active
06225259
ABSTRACT:
The present invention relates to a liquid formulation of ethyl (Z)-2-chloro-3-[2-chloro-5-(4,5,6,7-tetrahydro-1,3-dioxoisoindole ion-2-yl)phenyl]acrylate comprising, essentially, in addition to the above crop protection agent,
a) an ionic emulsifier,
b) a non-ionic emulsifier,
c) a non-nucleophilic and non-basic aromatic solvent and,
d) if desired, a further herbicidal crop protection agent.
The present invention furthermore relates to a method of controlling undesirable vegetation using this formulation.
EP-A 240 659 discloses the active ingredient ethyl (Z)-2-chloro-3-[2-chloro-5-(4,5,6,7-tetrahydro-1,3-dioxoisoindoledion-2-yl)-phenyl]acrylate for which “cinidon-ethyl” was proposed as common name. Furthermore, it can be seen clearly from this publication that the active ingredient is active against a series of dicotyledonous weeds under greenhouse conditions. However, the known formulations of this active ingredient are not completely satisfactory, in particular under field conditions.
Agric. Biol. Chem. 55 (11), (1991), pages 2677-2681 discloses that crop protection agents from the class of the N-aryl-3,4,5,6-tetrahydrophthalimides, for example the above cinidon-ethyl, may be subject to hydrolysis in the plant.
It is therefore an object of the present invention to provide a formulation of ethyl (Z)-2-chloro-3-[2-chloro-5-(4,5,6,7-tetrahydro-1,3-dioxoisoindoledion-2-yl)phenyl]acrylate in which this crop protection agent exerts a better biological activity combined with higher stability.
We have found that this object is achieved by the above-mentioned liquid formulation.
Moreover, we have found a method of controlling undesirable vegetation which utilizes this liquid formulation.
When preparing the formulation according to the invention, ethyl (Z)-2-chloro-3-[2-chloro-5-(4,5,6,7-tetrahydro-1,3-dioxoisoindoledion-2-yl)phenyl]acrylate is normally employed in a purity of from 80 to 100%.
This crop protection agent amounts normally to 5 to 50% by weight, in particular 10 to 30% by weight, of the liquid formulation according to the invention.
Especially suitable ionic emulsifiers are anionic surfactants, eg. alkali metal, alkaline earth metal or ammonium salts of the fatty acids, such as potassium stearate, alkyl sulfates, alkyl ether sulfates, alkyl- or iso-alkylsulfonates, alkylbenzenesulfonates such as sodium dodecylbenzenesulfonate and calcium dodecylbenzenesulfonate, alkylnaphthalenesulfonate, alkyl methyl ester sulfonates, acyl glutamates, alkylsuccinic ester sulfonates, sarcosinates such as sodium lauroyl sarcosinate and taurate. Mixtures of a plurality of these ionic emulsifiers are also suitable.
Preferred ionic emulsifiers are the salts of the alkylbenzenesulfonates and the alkylsulfosuccinates. Especially preferred ionic emulsifiers are the salts of alkylbenzenesulfonic acids, mainly calcium dodecylbenzenesulfonate and sodium dioctylsulfosuccinate, in particular calcium dodecylbezenesulfonate.
The ionic emulsifiers usually amount to from 2 to 20% by weight of the liquid formulation.
Suitable non-ionic emulsifiers are, for example, alkoxylated fats or oils of animal or vegetable origin such as maize oil ethoxylates, castor oil ethoxylates, tallow fat ethoxylates, glycerol esters such as glycerol monostearate, fatty alcohol alkoxylates and oxo-alcohol alkoxylates, fatty acid alkoxylates such as oleic acid ethoxylate, alkylphenyl alkoxylates such as isononyl-, isooctyl-, tributyl- and tristearylphenyl ethoxylates, fatty amine alkoxylates, fatty acid amide alkoxylates, sugar surfactants such as sorbitan fatty acid esters (sorbitan monooleate, sorbitan tristearate), polyoxyethylene sorbitan fatty acid esters, alkylpolyglycosides, N-alkylgluconamides, alkylmethyl sulfoxides, alkyldimethylphosphine oxides such as tetradecyldimethylphosphine oxide, and mixtures of such non-ionic emulsifiers.
Preferred non-ionic emulsifiers are ethoxylated or propoxylated naturally occurring carboxylic acids or alcohols, mainly ethoxylated oils such as castor oil ethoxylate having 36 to 50 ethylene oxide units.
The non-ionic emulsifiers in the liquid formulation normally amounts to from 2 to 20% by weight.
Suitable non-nucleophilic and non-basic aromatic solvents are cyclohexanone, halobenzenes such as chlorobenzene and liquid dichlorobenzenes, and also bromobenzene, alkylaromatics, preferably alkylbenzenes and alkylnaphthalenes whose alkyl groups have 1 to 20 carbon atoms, such as the Solvesso® series, eg. Solvesso® 100, Solvesso® 150 and Solvesso® 200 (Exxon Chemical) and mixtures of these, and methylbenzenes: toluene, o-xylene, m-xylene, p-xylene; ethylbenzene; iso-propylbenzene; tert-butylbenzene.
Mixtures of these are also suitable.
Preferred non-nucleophilic and non-basic aromatic solvents are Shellsol® products (Deutsche Shell Chemie GmbH) or Solvesso® products: Solvesso® 100, Solvesso® 150, Solvesso® 200, in particular Solvesso® 200.
The solvent generally amounts to so much of the liquid formulation that the total of all components is 100% by weight.
The liquid formulations according to the invention may additionally comprise other active ingredients conventionally used in crop protection, eg. other herbicidally, fungicidally and insecticidally active or growth-regulating active ingredients.
Herbicidal crop protection agents which are preferred as further active ingredients conventionally used in crop protection are those from the group below: ethyl 2-chloro-3-[2-chloro-4-fluoro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenyl]propionate (F8426), diflufenzopyr, dimethenamid, flamprop-methyl, propanil, aryloxyalkanecarboxylic acids and their esters such as 2,4-D, 2,4-DB, dichlorprop, dichlorprop-P (2,4-DP-P), MCPA, MCPB, mecoprop, mecoprop-P and [(4-amino-3,5-dichloro-6-fluoro-2-pyridyl)oxy]acetic acid (fluroxypyr), benzoic acids such as chloramben, dicamba, benzothiadiazinones such as bentazone, bleachers such as clomazone (dimethazone), diflufenican, fluorochloridone, flupoxam, fluridone, pyrazolate, sulcotrione (chlormesulone), carbamates such as carbetamide, chlorbufam, chlorpropham, desmedipham, phenmedipham, vernolate, quinolinecarboxylic acids such as quinclorac, quinmerac, dinitroanilines such as butralin, fluchloralin, isopropalin, nitralin, oryzalin, pendimethalin, prodiamine, profluralin, trifluralin, dinitrophenols such as bromofenoxim, dinoseb, dinoseb-acetate, dinoterb, DNOC, minoterb-acetate, diphenyl ethers such as acifluorfen-sodium, aclonifen, bifenox, chlornitrofen (CNP), difenoxuron, ethoxyfen, fluorodifen, fluoroglycofen-ethyl, fomesafen, furyloxyfen, lactofen, nitrofen, nitrofluorfen, oxyfluorfen, phenols such as bromoxynil, ioxynil, phenoxyphenoxypropionic esters such as clodinafop, cyhalofop-butyl, diclofop-methyl, fenoxaprop-ethyl, fenoxaprop-p-ethyl, fenthiapropethyl, fluazifop-butyl, fluazifop-p-butyl, haloxyfop-ethoxyethyl, haloxyfop-methyl, haloxyfop-p-methyl, isoxapyrifop, propaquizafop, quizalofop-ethyl, quizalofop-p-ethyl, quizalofop-tefuryl, pyridazines such as chloridazon, maleic hydrazide, norflurazon, pyridate, pyridinecarboxylic acids such as clopytalid, dithiopyr, picloram, thiazopyr, uracils such as bromacil, lenacil, terbacil and crop protection agents of the cyclohexanone type such as sethoxydim, cycloxydim, clethodim, tralkoxydim, butroxydim, 2-(1-(3-chloroallyloxy)iminopropyl)-5-(tetrahydropyran-4-yl)-3-hydroxycyclohex-2-enone and 2-(l-(2-p-chlorophenoxypropyloxy)-iminobutyl-5-(tetrahydrothiopyran-3-yl)-3-hydroxycyclohex-2-enone.
Herbicidal crop protection agents which are especially preferred as further active ingredients conventionally used in crop protection are those from the group below: ethyl 2-chloro-3-[2-chloro-4-fluoro-5-(4-difloromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenyl]propionate (F8426), dimetheneamid, dinitroanilines such as pendimethalin, crop protection agents of the cyclohexenone type such as sethoxydim, cycloxydim, clethodim, tralkoxydim, butroxydim, 2-(1-(3-chloroallyloxy)-iminopropyl)-5-(tetrahydropyran-4-yl)
Berghaus Rainer
Bratz Matthias
Kleuser Dieter
Nuyken Wessel
Parg Adolf
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