EP2560487A1 - Composition insecticide et/ou herbicide à action améliorée, à base de dérivés d'acide tétramique à substituants spirohétérocycliques - Google Patents

Composition insecticide et/ou herbicide à action améliorée, à base de dérivés d'acide tétramique à substituants spirohétérocycliques

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Publication number
EP2560487A1
EP2560487A1 EP11716228A EP11716228A EP2560487A1 EP 2560487 A1 EP2560487 A1 EP 2560487A1 EP 11716228 A EP11716228 A EP 11716228A EP 11716228 A EP11716228 A EP 11716228A EP 2560487 A1 EP2560487 A1 EP 2560487A1
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EP
European Patent Office
Prior art keywords
alkyl
substituted
alkoxy
optionally
chlorine
Prior art date
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Withdrawn
Application number
EP11716228A
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German (de)
English (en)
Inventor
Reiner Fischer
Stefan Lehr
Olga Malsam
Rolf Pontzen
Elmar Gatzweiler
Rainer Süssmann
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Bayer Intellectual Property GmbH
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Bayer Intellectual Property GmbH
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Priority to EP11716228A priority Critical patent/EP2560487A1/fr
Publication of EP2560487A1 publication Critical patent/EP2560487A1/fr
Withdrawn legal-status Critical Current

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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
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/12—Quaternary ammonium compounds
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • the present invention relates to the enhancement of the action of crop protection agents containing in particular spiroheterocyclisch-substituted tetramic acid derivatives, by the addition of ammonium or phosphonium salts and optionally penetration promoters, the corresponding agents, processes for their preparation and their use in crop protection as insecticides and / or acaricides and / or to prevent undesired plant growth.
  • EP-A-0 262 399 and GB-A-2 266 888 disclose similarly structured compounds (3-aryl-pyrrolidine-2,4-diones), of which, however, no herbicidal, insecticidal or acaricidal activity has become known .
  • Unsubstituted, bicyclic 3-arylpyrrolidine-2,4-dione derivatives (EP-A-355 599, EP-A-415 211 and JP-A-12-053) are known to have herbicidal, insecticidal or acaricidal activity 670) and substituted monocyclic 3-arylpyrrolidine-2,4-dione derivatives (WO 10/066780, EP-A-377 893 and EP-A-442 077).
  • EP-A-442 073 polycyclic 3-arylpyrrolidine-2,4-dione derivatives
  • EP-A-456 063 EP-A-521 334, EP-A- 596 298, EP-A-613 884, EP-A-613 885, WO 95/01 971, WO 95/26 954, WO 95/20 572, EP-A-0 668 267, WO 96/25 395, WO 96/35 664, WO 97/01 535, WO 97/02 243, WO 97/36 868, WO 97/43275, WO 98/05638, WO 98/06721, WO 98/25928, WO 99/24437, WO 99 / 43649, WO 99/48869 and WO 99/55673, WO 01/17972, WO 01/23354, WO 01/74770, WO 03/013249,
  • ketoenols 1H-arylpyrrolidine-2,4-diones from WO 99/16748 and (spiro) ketal-substituted N-alkoxy-alkoxy-substituted aryl-pyrrolidinediones are found in JP-A-14 205 984 and Ito M. et al. Bioscience , Biotechnology and Biochemistry 67, 1230-1238, (2003).
  • the addition of safeners to ketoenols is also known in principle from WO 03/013249. Besides, they are from WO 06/024411 herbicidal agents containing ketoenols known.
  • salts of sulfonic acids in which the acids themselves paralyze acting on insects (US 2,842,476).
  • An increase in activity e.g. ammonium sulphate, for example, describes e for the herbicidal glyphosate, phosphinothricin and for phenyl-substituted cyclic ketoenols (US Pat. No. 6,645,914, EP-A2 0 036 106, for example WO 07/068427).
  • a corresponding increase in insecticidal activity has already been demonstrated by e.g. WO 07/068428.
  • the use of ammonium sulfate as a formulation aid is described for certain active ingredients and applications (WO 92/16108), but it is there to stabilize the formulation, not to increase the effect.
  • the present invention thus relates to the use of ammonium or phosphonium salts to increase the efficacy of plant protection products containing herbicidal and / or insecticidal and / or acaricidal spiroheterocyclisch-substituted tetramic acid derivatives of the formula (I) as an active ingredient.
  • the invention also relates to compositions containing herbicidal and / or acaricidal and / or insecticidal spiroheterocyclic-substituted tetramic acid derivatives of the formula (I) and the activity-enhancing ammonium or phosphonium salts, both formulated active ingredients and ready-to-use agents (spray liquors).
  • the invention further relates to the use of these agents for controlling noxious insects and / or spider mites and / or undesired plant growth.
  • Active Ingredients According to the Invention from the Class of Spiroheterocyclic-Substituted Tetramic Acid Derivatives whose effect can be increased by the addition of ammonium or phosphonium salts to the formulated or ready-to-use active compound preparations are defined by formula (I),
  • X is halogen, alkyl, alkenyl, alkynyl, optionally substituted by
  • Y and Z independently of one another represent hydrogen, alkyl, alkenyl, alkynyl, optionally substituted cycloalkyl optionally interrupted by heteroatoms, halogen, alkoxy, haloalkyl or haloalkoxy,
  • A is hydrogen, in each case optionally substituted alkyl, alkenyl, alkynyl, alkoxyalkyl, phenylalkyl, hetarylalkyl or a group G,
  • G is hydrogen (a) or one of the groups
  • E is a metal ion or an ammonium ion
  • L is oxygen or sulfur
  • M is oxygen or sulfur
  • R! represents in each case optionally halogen or cyano-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl or represents in each case optionally halogen, alkyl or alkoxy-substituted cycloalkyl or heterocyclyl or in each case optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl in each case optionally halogen or cyano-substituted alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl or represents in each case optionally substituted cycloalkyl, phenyl or benzyl,
  • R 1, R 4 and R 1 independently of one another are each optionally halogen-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio or cycloalkylthio or in each case optionally substituted phenyl, benzyl, phenoxy or phenylthio,
  • R ⁇ and R ⁇ are each independently hydrogen, each optionally substituted by halogen or cyano alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, each optionally substituted phenyl or benzyl, or together with the N-atom to which they are attached , form an optionally oxygen or sulfur containing and optionally substituted cycle.
  • the compounds of the formula (I) can also be present in different compositions as optical isomers or mixtures of isomers, which can optionally be separated in a customary manner. Both the pure isomers and the mixtures of isomers, their preparation and use and agents containing them are the subject of the present invention. In the following, however, for the sake of simplicity, reference is always made to compounds of the formula (I), although both the pure compounds and, if appropriate, mixtures with different proportions of isomeric compounds are meant.
  • A, E, L, M, W, X, Y, Z, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 have the meanings given above.
  • the compounds of the formula (I) are prepared, in particular, by the processes described in WO 2009/049851 and in the literature mentioned in the introduction.
  • W is preferably hydrogen, halogen, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, optionally substituted C 3 -C 6 -cycloalkyl, which may optionally be interrupted by oxygen or sulfur, C 1 -C 6 -alkyl, C 2 -C 6 -alkoxy, C 1 -C -halogenoalkyl, C 1 -C 4 -halogenoalkoxy or cyano, X preferably represents halogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, optionally substituted C 3 -C -cycloalkyl, which may be replaced by oxygen or Sulfur may be interrupted, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkoxy, C 3 -C 6 -haloalkoxy or cyano,
  • Y and Z are preferably, independently of one another, hydrogen, halogen, C 1 -C 6 -alkyl, C 2 -C 4 -alkyl, Alkenyl, C 2 -C 6 -alkynyl, optionally substituted C 3 -C 6 -cycloalkyl, which may optionally be interrupted by oxygen or sulfur, C 2 -C 6 -alkoxy, C 3 -C 6 -haloalkyl, C 2 -C 6 -haloalkoxy,
  • A is preferably hydrogen, C 1 -C 6 -alkyl, C 3 -C 9 -alkenyl, C 3 -C 9 -alkynyl, C 1 -C 6 -halogenoalkyl, C 2 -C 6 -cycloalkyl, C 4 -alkoxy-C 1 -C 4 -alkyl, in each case optionally mono- or polysubstituted by halogen, C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy, C 2 -C 2 -haloalkyl, C 1 -C 2 -haloalkoxy or cyano-substituted phenyl- (C 1 -C 2) -alkyl, hetaryl- (C 1 C2) alkyl or a group G,
  • G is preferably hydrogen (a) or one of the groups
  • E is a metal ion or an ammonium ion
  • L is oxygen or sulfur
  • M is oxygen or sulfur
  • R! preferably represents each optionally halogen- or cyano-substituted CT-C20-alkyl, C 2 -C 2 o-alkenyl, C j -Cg -alkoxy-C j -Cg-alkyl, C j -Cg-alkylthio-C j -Cg -alkyl or poly-C j -Cg -alkoxy-Ci-Cg-alkyl or C3-Cg-cycloalkyl optionally substituted by halogen, C j -C ⁇ -alkyl or C j -C ⁇ -alkoxy, in which optionally one or two are not directly adjacent methylene groups are replaced by oxygen and / or sulfur, optionally substituted by halogen, cyano, nitro, C j -C ⁇ alkyl, C ⁇ -C ⁇ alkoxy, C j -C ⁇ haloalkyl, C ⁇ -C ⁇ haloal
  • R 2 preferably represents in each case optionally halogen- or cyano-substituted C -C 2 -alkyl, C 2 -C 2 o-alkenyl, C 1 -C 8 -alkoxy-C 2 -C 8 -alkyl or poly-C 1 -C 8 -alkoxy-C 2 -C 8 -alkyl, j is optionally substituted by halogen, C j -CSS-alkyl or C -CSS-substituted C 3 -C 8 - cycloalkyl, or represents in each case optionally substituted by halogen, cyano, nitro, C j -C ⁇ -alkyl, C j -C ⁇ -alkoxy, C-C ⁇ -haloalkyl or C -C ⁇ -haloalkoxy-substituted phenyl or benzyl,
  • R ⁇ preferably represents optionally halogen-substituted C ⁇ -C 8 -alkyl or in each case optionally substituted by halogen, C j -CSS-alkyl, CT -CSS-alkoxy, C1-C4-haloalkyl, C1-C4 haloalkoxy, cyano or Nitro substituted phenyl or benzyl,
  • R 1 and R 2 independently of one another preferably represent in each case optionally halogen-substituted C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, C 1 -C 8 -alkylamino, di- (C 1 -C 8 -alkyl) amino, C 1 -C 8 -alkylthio or C 3 -C 8 -alkenylthio or represent in each case optionally halogen, nitro, cyano, C 4 -haloalkylthio, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl-substituted phenyl, phenoxy or phenylthio,
  • R ⁇ and R ⁇ are, independently of one another preferably represent hydrogen, represent in each case optionally substituted by halogen or cyano, C 1 -C 8 alkyl, C 3 C 8 cycloalkyl, C 1 -C 8 alkoxy, C 3 C 8 alkenyl, or C 1 -C 8 -alkoxy-C 2 -C 8 -alkyl, in each case optionally substituted by halogen, C 1 -C 8 alkyl, C 1 -C 8 -haloalkyl or C 1 -C 8 -alkoxy-substituted phenyl or benzyl or together form an optionally substituted by C j -C ⁇ -alkyl C3-C-alkylene kylenrest in which optionally a methylene group by oxygen or sulfur is replaced.
  • halogen is fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.
  • W is particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, optionally once or twice by fluorine, chlorine, methyl,
  • X particularly preferably represents chlorine, bromine, iodine, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, optionally C3-C which is mono- to disubstituted by fluorine, chlorine, methyl, cyclopropyl, methoxy or cyano Cycloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl or C 1 -C 4 haloalkoxy,
  • Y and Z are particularly preferably and independently of one another hydrogen, fluorine, chlorine, bromine, iodine, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, optionally once or twice by fluorine, chlorine, methyl, cyclopropyl , Methoxy or cyano-substituted C 3 -C -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl or C 1 -C 4 -haloalkoxy,
  • E is a metal ion or an ammonium ion, is oxygen or sulfur and is oxygen or sulfur, particularly preferably represents in each case optionally mono- to trisubstituted by fluorine or chlorine-substituted Ci-Ci-alkyl, C2-Ci g-alkenyl, C-Cg-alkoxy-C j - C / j-alkyl, Ci -Cg- alkylthio-C 1 -C 4 alkyl or poly-C j -CG-alkoxy-Cj-C4-alkyl or represents optionally mono- to disubstituted by fluorine, chlorine, C 1 -C5- Alkyl or C 1 -C 5 -alkoxy-substituted C 3 -C -cycloalkyl in which optionally one or two not directly adjacent methylene groups are replaced by oxygen and / or sulfur, optionally mono- to trisubstituted by fluorine, chlorine, bromine, cyano
  • R 1 and R 2 independently of one another particularly preferably represent hydrogen, in each case optionally mono- to trisubstituted by fluorine or chlorine, C 1 -C 6 -alkyl, C 3 -C 9 -cycloalkyl, C 1 -C 6 -alkoxy, C 3 -C 6 -alkenyl or C 1 -C 4 -cycloalkyl; C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, phenyl which is optionally monosubstituted to trisubstituted by fluorine, chlorine, bromine, C 5 -C 5 -haloalkyl, C 1 -C 5 -alkyl or C 1 -C 5 -alkoxy, or together for one optionally C 1 -C 4 -alkyl-substituted C 3 -C -alkylene radical in which optionally a methylene group is replaced by oxygen or sulfur.
  • halogen is fluorine, chlorine and bromine, in particular fluorine and chlorine.
  • W is very particularly preferably hydrogen, chlorine, bromine, methyl, ethyl, methoxy or ethoxy, (particularly preferably hydrogen, methyl or ethyl),
  • X is very particularly preferably chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy, propoxy, cyclopropyl or trifluoromethyl, (particularly preferably methyl or ethyl),
  • Y and Z are very particularly preferably each independently hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, cyclopropyl, trifluoromethyl, trifluoromethoxy or
  • Trifluoroethoxy (especially preferably independently of one another hydrogen or methyl),
  • A is very particularly preferably methyl, ethyl or propyl, (particularly preferably methyl or ethyl), G is very particularly preferably hydrogen (a) or one of the groups or E (f),
  • E is a metal ion or an ammonium ion
  • L is oxygen or sulfur (especially preferably oxygen)
  • M is oxygen or sulfur, (particularly preferably oxygen)
  • R 1 very particularly preferably in each case optionally monosubstituted to trisubstituted by fluorine or chlorine-substituted Ci -C Q alkyl, C2-Ci () alkenyl, C ⁇ -C / j-alkoxy-Ci-C2-alkyl, Ci - C4-alkylthio-C1-C2-alkyl or optionally monosubstituted by fluorine C3-C cycloalkyl substituted by chlorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, methoxy, ethoxy, trifluoromethyl or trifluoromethoxy optionally substituted once or twice by chlorine, methyl, ethyl or methoxy substituted
  • R 2 particularly preferably represents in each case optionally mono- to trisubstituted by fluorine or chlorine-substituted C 1 -C -Q-alkyl, C 2 -C 1 () -alkenyl or C 1 -C 4 -alkoxy-C 2 -C 4 -alkyl, for cyclopentyl or cyclohexyl or each optionally optionally mono- to disubstituted by fluorine, chlorine, cyano, nitro, methyl, ethyl, methoxy, trifluoromethyl or trifluoromethoxy substituted phenyl or benzyl (especially preferably for C -C Q-alkyl).
  • the general or preferred radical definitions or ternations listed can be combined with one another as desired, that is to say also between the respective ranges and ranges. They apply to the end products as well as to the pre- and Intermediates accordingly.
  • Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl
  • heteroatoms e.g. in alkoxy, as far as possible, in each case straight-chain or branched.
  • optionally substituted radicals may be monosubstituted or polysubstituted, with multiple substituents the substituents being the same or different.
  • the active compounds can be used in the compositions according to the invention in a wide concentration range.
  • concentration of the active ingredients in the formulation is usually 0, 1 - 50 wt .-%.
  • Ammonium and phosphonium salts which according to the invention increase the effect of crop protection agents containing compounds of the formula (I), are defined by formula ( ⁇ )
  • D is nitrogen or phosphorus
  • D is preferably nitrogen
  • R, R, R and R independently of one another represent hydrogen or in each case optionally substituted C 1 -C 6 -alkyl or mono- or polyunsaturated, optionally substituted C 1 -C 6 -alkylene, where the substituents can be selected from halogen, nitro and cyano,
  • R, R, R and R are each, independently of one another, hydrogen or in each case optionally substituted C 1 -C 8 -alkyl, where the substituents may be selected from halogen, nitro and cyano,
  • R, R, R and R particularly preferably independently of one another represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl or t-butyl,
  • R, R, R / ö ⁇ and R very particularly preferably represents hydrogen, n is 1, 2, 3 or 4, n is preferably 1 or 2; R 30
  • R 30 is preferably hydrogencarbonate, tetraborate, fluoride, bromide, iodide, chloride, monohydrogenphosphate, dihydrogenphosphate, hydrogensulphate, tartrate, sulphate, nitrate, thiosulphate, thiocyanate, formate, lactate, acetate, propionate, butyrate, pentanoate or oxalate,
  • R 30 particularly preferably represents lactate, monohydrogenphosphate, dihydrogen phosphate, sulphate, nitrate, thiosulphate, thiocyanate, oxalate or formate,
  • R 30 is particularly preferably sulfate.
  • ammonium sulfate Likewise emphasized is diammonium hydrogen phosphate
  • the ammonium and phosphonium salts of the formula (I) can be used in a broad concentration range for increasing the effect of crop protection agents containing spiroheterocyclic-substituted tetramic acid derivatives of the formula (I).
  • the ammonium or phosphonium salts in the ready-to-use crop protection agent are used in a concentration of 0.5 to 80 mmol / l, preferably 0.75 to 37.5 mmol / l, particularly preferably 1.5 to 25 mmol / l.
  • the ammonium and / or phosphonium salt concentration in the formulation is selected to be in the specified general, preferred or more preferred ranges after dilution of the formulation to the desired drug concentration.
  • the concentration of the salt in the formulation is usually 1-50 wt .-%.
  • a penetration promoter is added to the crop protection agents to increase the effect. It can be described as completely surprising that even in these cases an even greater increase in activity can be observed.
  • the present invention thus also relates to the use of a combination of penetrants and ammonium and / or phosphonium salts to increase the efficacy of crop protection agents, the insecticidal and / or acaricidal and / or herbicidal, spiroheterocyclisch-substituted tetramic acid derivatives of the formula (I) as an active ingredient contain.
  • the invention also relates to compositions containing herbicidal and / or acaricidal and / or insecticidal spiroheterocyclisch- substituted tetramic acid derivatives of the formula (I), penetrants and ammonium and / or phosphonium salts both formulated active ingredients and ready-to-use agents (spray liquors ).
  • the subject of the invention is the use of these Means for controlling insect pests, spider mites and / or plant growth.
  • Suitable penetration promoters in the present context are all those substances which are usually used to improve the penetration of agrochemical active substances into plants.
  • Penetration promoters are defined in this context by the fact that they can penetrate from the aqueous spray mixture and / or from the spray coating in the cuticle of the plant and thereby increase the material mobility (mobility) of active ingredients in the cuticle.
  • the method described in the literature can be used to determine this property.
  • Suitable penetration promoters are, for example, alkanol alkoxylates.
  • Penetration promoters according to the invention are alkanol alkoxylates of the formula (IV)
  • R is straight-chain or branched alkyl having 4 to 20 carbon atoms
  • R ' is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl or n-hexyl,
  • AO stands for an ethylene oxide radical, a propylene oxide radical, a butylene oxide radical or mixtures of ethylene oxide and propylene oxide radicals or butylene oxide radicals and v stands for numbers from 2 to 30.
  • a preferred group of penetrants are alkanol alkoxylates of the formula R-0 - (- EO-) n -R '(IV ' -a) in which
  • R is as defined above, R 'is as defined above, EO is -CH 2 -CH 2 -O- and n is from 2 to 20.
  • Another preferred group of penetration enhancers are alkanol alkoxylates of the formula R-0 - (- EO-) p - (- PO-) q -R '(IV ⁇ -b) in which
  • R has the meaning given above, R 'has the meaning given above,
  • EO stands for -CH 2 -CH 2 -0-
  • CH 3 p is a number from 1 to 10 and q is a number from 1 to 10.
  • Another preferred group of Penetrationsiorderem are alkanol alkoxylates of the formula
  • R has the abovementioned meaning, R 'has the abovementioned meaning, EO stands for -CH 2 -CH 2 -O-,
  • CH 3 r is a number from 1 to 10 and s is a number from 1 to 10.
  • Another preferred group of penetration enhancers are alkanol alkoxylates of the formula R-O - (- EO-) D - (- BO-) a -R '(IV'-d) in which
  • EO stands for -CH 2 -CH 2 -0-
  • CH 3 p stands for numbers from 1 to 10
  • q stands for numbers from 1 to 10.
  • a further preferred group of Penetrationsiorderem are alkanol alkoxylates of the formula R-0 - (- BO) r - (- EO-) s -R '(IV ⁇ -e)
  • EO stands for -CH 2 -CH 2 -0-
  • s stands for numbers from 1 to 10.
  • Another preferred group of penetration enhancers are alkanol alkoxylates of the formula CH 3 - (CH 2 ) T -CH 2 -0 - (- CH 2 -CH 2 -O-) U -R '(IV ⁇ -f) in which
  • R is preferably butyl, i-butyl, n-pentyl, i-pentyl, neopentyl, n-hexyl, i-hexyl, n-octyl, i-octyl, 2-ethyl-hexyl, nonyl, i-nonyl, decyl, n Dodecyl, i-dodecyl, lauryl, myristyl, i-tridecyl, trimethyl-nonyl, palmityl, stearyl or eicosyl.
  • an alkanol alkoxylate of the formula (IV'-c) is 2-ethyl-hexyl alkoxylate of the formula (IV'-c) is 2-ethyl-hexyl alkoxylate of the formula (IV'-c) is 2-ethyl-hexyl alkoxylate of the formula (IV'-c) is
  • EO stands for -CH 2 -CH 2 -0-
  • EO stands for -CH 2 -CH 2 -0-
  • BO stands for - CH - CH -CH -0 stands for
  • alkanol alkoxylates of the formula (IV-f) are compounds of this formula in which t is a number from 9 to 12 and u is a number from 7 to 9 stands.
  • alkanol alkoxylate of the formula (IV'-f-1) very particular preference is given to alkanol alkoxylate of the formula (IV'-f-1)
  • alkanol alkoxylates are generally defined by the above formulas. These substances are mixtures of substances of the specified type with different chain lengths. For the indices, therefore, average values are calculated, which can also differ from whole numbers.
  • alkanol alkoxylates of the stated formulas are known and are in some cases commercially available (for example under the trade names Genapol, Marlipal, Lutensol, Renex) or can be prepared by known methods (compare WO 98/35553, WO 00/35 278 and EP-A 0 681 865).
  • Suitable penetration promoters are substances which promote the availability of the compounds of the formula (I) in the spray coating. These include, for example, mineral or vegetable oils. Suitable oils are all mineral or vegetable, optionally modified, oils which can usually be used in agrochemical compositions. Examples include sunflower oil, rapeseed oil, olive oil, castor oil, rapeseed oil, corn kernel oil, cottonseed oil and soybean oil or the esters of said oils. Rape oil, sunflower oil and their methyl or ethyl esters are preferred. Highlighted is rapeseed oil methyl ester.
  • the concentration of penetration promoter can be varied within a wide range in the agents according to the invention.
  • a formulated crop protection agent it is generally from 1 to 95% by weight, preferably from 1 to 55% by weight, more preferably from 15 to 40% by weight.
  • the concentration is generally between 0.1 and 10 g / l, preferably between 0.5 and 5 g / l.
  • Plant protection agents according to the invention may also contain further components, for example surfactants or dispersing aids or emulsifiers.
  • non-ionic surfactants or dispersing agents they all usually come in agrochemical Agents usable materials of this type into consideration.
  • polyethylene oxide-polypropylene oxide block copolymers polyethylene glycol ethers of linear alcohols, reaction products of fatty acids with ethylene oxide and / or propylene oxide, furthermore polyvinyl alcohol, polyvinylpyrrolidone, copolymers of polyvinyl alcohol and polyvinylpyrrolidone and copolymers of (meth) acrylic acid and (meth) acrylic acid esters, furthermore Alkyl ethoxylates and alkylaryl ethoxylates, which may optionally be phosphated and optionally neutralized with bases, wherein sorbitol ethoxylates may be mentioned by way of example, and polyoxyalkyleneamine derivatives.
  • Suitable anionic surfactants are all substances of this type which can usually be used in agrochemical compositions. Preference is given to alkali metal and alkaline earth metal salts of alkyl sulfonic acids or alkylaryl sulfonic acids.
  • anionic surfactants or dispersing agents are salts of polystyrenesulfonic acids which are sparingly soluble in vegetable oil, salts of polyvinylsulfonic acids, salts of naphthalenesulfonic acid-formaldehyde condensation products, salts of condensation products of naphthalenesulfonic acid, phenolsulfonic acid and formaldehyde and salts of lignin sulfonic acid.
  • Suitable additives which may be present in the formulations according to the invention are emulsifiers, foam-inhibiting agents, preservatives, antioxidants, dyes and inert fillers.
  • Preferred emulsifiers are ethoxylated nonylphenols, reaction products of alkylphenols with ethylene oxide and / or propylene oxide, ethoxylated arylalkylphenols, furthermore ethoxylated and propoxylated arylalkylphenols, and sulfated or phosphated arylalkyl ethoxylates or ethoxy-propoxylates, sorbitan derivatives such as polyethylene oxide sorbitan fatty acid esters and sorbitan Fatty acid esters, may be mentioned as examples.
  • Penetration promoter means that any compound which acts as a penetration promoter in the test for cuticle penetration (Baur et al., 1997, Pesticide Science 51, 131-152) is suitable.
  • Example 1 Increasing the Effectiveness of Ammonium / Phosphonium Salts in Combination with Penetration Promoters
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • ammonium or phosphonium salts and penetration promoters these are each added to the spray mixture at a concentration of 1000 ppm.
  • Paprika plants Capsicum annuum which are heavily infested with the green peach aphid ⁇ Myzus persicae) are treated by drip irrigation with the preparation of active compound in the desired concentration. After the desired time the kill is determined in%. 100% means that all animals have been killed; 0% means that no animals were killed.
  • RME rapeseed oil methyl ester
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration. For use with ammonium or phosphonium salts and penetrants (rapeseed oil methyl ester 500 EW), these are each added at a concentration of 1000 ppm a.i. added to the spray mixture. Cotton plants (Gossypium hirsutum) which are heavily infested with the cotton aphid ⁇ Aphis gossypii) are treated by drip irrigation with the preparation of active compound in the desired concentration.
  • the kill is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed. table
  • the isolation of the cuticles is carried out in such a way that initially marked on the bottom with dye and punched leaf discs are filled by vacuum infiltration with a buffered to a pH value between 3 and 4 pectinase solution (0.2 to 2%), then sodium azide and the treated leaf discs are allowed to stand until the original leaf structure is dissolved and the non-cellular cuticle is detached.
  • the cuticles are placed with a pair of tweezers on the center of the coated with silicone grease edges of the diffusion cells and sealed with a likewise greased ring.
  • the arrangement is chosen such that the morphological outer side of the cuticles is directed outwards, ie towards the air, while the original inner side faces the interior of the diffusion cell.
  • the diffusion cells are filled with a 30% ethylene glycol / water solution.
  • 10 ⁇ l of the spray mixture of the following composition are applied to the outside of the cuticle.
  • the preparation of the spray mixture is carried out with local tap water medium water hardness.
  • the water is allowed to evaporate, the chambers are turned over and placed in thermostated baths containing the temperature and humidity above the cuticle adjustable to the cuticle with the spray coating by a slight air flow (20 ° C, 60% rh). At regular intervals aliquots are taken from an autosampler and the active ingredient content is determined by HPLC.
  • test results are shown in the following table.
  • the figures given are average values from 8 to 10 measurements. It can clearly be seen that even the ammonium salts alone significantly improve the penetration and, together with RME, have a superadditive (synergistic) effect.
  • RME rapeseed oil methyl ester (use formulated as 500 EW, concentration in g active substance / 1)
  • DAHP diammonium hydrogen phosphate
  • Example 5 Increasing the penetration into the plant by ammonium or phosphonium salts and synergistic increase of the penetration into the plant by ammonium / phosphonium salts in combination with penetration promoters
  • the isolation of the cuticles is carried out in such a way that initially marked on the bottom with dye and punched leaf discs are filled by vacuum infiltration with a buffered to a pH value between 3 and 4 pectinase solution (0.2 to 2%), then sodium azide and the treated leaf discs are allowed to stand until the original leaf structure is dissolved and the non-cellular cuticle is detached.
  • the cuticles are placed with a pair of tweezers on the center of the coated with silicone grease edges of the diffusion cells and sealed with a likewise greased ring.
  • the arrangement has been chosen such that the morphological outer side of the cuticles was directed outwards, ie towards the air, while the original inner side faces the interior of the diffusion cell.
  • the diffusion cells are filled with a 30% ethylene glycol / water solution.
  • 10 ⁇ l of the spray mixture of the following composition are applied to the outside of the cuticle.
  • the preparation of the spray mixture is carried out with local tap water medium water hardness.
  • the water is allowed to evaporate, the chambers are turned over and placed in thermostated baths containing the temperature and humidity above the cuticle adjustable to the cuticle with the spray coating by a slight air flow (35 ° C, 60% rh). At regular intervals aliquots are taken from an autosampler and the active ingredient content is determined by HPLC.
  • test results are shown in the following table.
  • the figures given are average values from 8 to 10 measurements. It can clearly be seen that even the ammonium salts alone significantly improve the penetration and, together with RME, have a superadditive (synergistic) effect.
  • RME rapeseed oil methyl ester (use formulated as 500 EW, concentration in g of active ingredient /
  • RME rapeseed oil methyl ester (use formulated as 500 EW, concentration in g active substance / 1)

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne l'augmentation de l'action d'agents phytoprotecteurs renfermant en particulier des dérivés de l'acide tétramique à substituants spirohétérocycliques de formule (I), par addition de sels d'ammonium ou de sels de phosphonium et, le cas échéant, d'agents facilitant la pénétration. L'invention concerne également les produits correspondants, leurs procédés de production et leur utilisation dans la protection des plantes, comme insecticides et/ou comme acaricides et/ou pour empêcher la croissance non désirée de plantes.
EP11716228A 2010-04-20 2011-04-18 Composition insecticide et/ou herbicide à action améliorée, à base de dérivés d'acide tétramique à substituants spirohétérocycliques Withdrawn EP2560487A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP11716228A EP2560487A1 (fr) 2010-04-20 2011-04-18 Composition insecticide et/ou herbicide à action améliorée, à base de dérivés d'acide tétramique à substituants spirohétérocycliques

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US32589310P 2010-04-20 2010-04-20
EP10160451 2010-04-20
EP11716228A EP2560487A1 (fr) 2010-04-20 2011-04-18 Composition insecticide et/ou herbicide à action améliorée, à base de dérivés d'acide tétramique à substituants spirohétérocycliques
PCT/EP2011/056136 WO2011131623A1 (fr) 2010-04-20 2011-04-18 Composition insecticide et/ou herbicide à action améliorée, à base de dérivés d'acide tétramique à substituants spirohétérocycliques

Publications (1)

Publication Number Publication Date
EP2560487A1 true EP2560487A1 (fr) 2013-02-27

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Country Status (5)

Country Link
US (1) US8889592B2 (fr)
EP (1) EP2560487A1 (fr)
CN (1) CN102939007B (fr)
BR (1) BR112012027044A8 (fr)
WO (1) WO2011131623A1 (fr)

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TWI572282B (zh) * 2011-11-30 2017-03-01 先正達合夥公司 含有螺雜環吡咯啶二酮的殺有害生物混合物
WO2019197635A1 (fr) 2018-04-13 2019-10-17 Bayer Aktiengesellschaft Formulation de mélanges insecticides avec du carbonate de propylène
TW202128014A (zh) 2019-10-10 2021-08-01 德商拜耳廠股份有限公司 含二醇醚溶劑之殺蟲劑調配物
US20220330546A1 (en) 2019-10-10 2022-10-20 Bayer Aktiengesellschaft Formulation of insecticides comprising propylene carbonate
TW202128015A (zh) 2019-10-10 2021-08-01 德商拜耳廠股份有限公司 包含乙二醇醚溶劑之殺昆蟲混合物調配物

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US20110281727A1 (en) 2011-11-17
WO2011131623A1 (fr) 2011-10-27
CN102939007B (zh) 2015-09-02
BR112012027044A8 (pt) 2017-10-10
CN102939007A (zh) 2013-02-20
US8889592B2 (en) 2014-11-18
BR112012027044A2 (pt) 2015-09-29

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