EP2157856A1 - Herbizid wirksame zusammensetzung - Google Patents

Herbizid wirksame zusammensetzung

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Publication number
EP2157856A1
EP2157856A1 EP08760878A EP08760878A EP2157856A1 EP 2157856 A1 EP2157856 A1 EP 2157856A1 EP 08760878 A EP08760878 A EP 08760878A EP 08760878 A EP08760878 A EP 08760878A EP 2157856 A1 EP2157856 A1 EP 2157856A1
Authority
EP
European Patent Office
Prior art keywords
methyl
benzyl
ethyl
dioxopiperazin
dione
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP08760878A
Other languages
German (de)
English (en)
French (fr)
Inventor
Eike Hupe
William Karl Moberg
Robert Reinhard
Bernd Sievernich
Elmar Kibler
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to EP08760878A priority Critical patent/EP2157856A1/de
Publication of EP2157856A1 publication Critical patent/EP2157856A1/de
Withdrawn legal-status Critical Current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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/46—N-acyl derivatives
    • 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
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines

Definitions

  • the present invention relates to herbicidally active compositions containing at least one piperazinedione compound and at least one further compound selected from herbicidally active compounds and safeners.
  • the herbicides can be used only in a narrow time window in order to achieve the desired herbicidal action, wherein the time window can be influenced in an unpredictable manner by weather conditions.
  • Methine group linked aryl or hetaryl and in the 6-position have a linked via a methyl group aryl or hetaryl
  • the object of the invention is to provide herbicidal compositions which have a high activity against unwanted harmful plants.
  • the compositions should at the same time have good crop tolerance.
  • the compositions of the invention should show a broad spectrum of activity.
  • the present invention relates to herbicidally active compositions comprising: A) at least one piperazinedione compound of the formula I.
  • R x , R y are each hydrogen or together are a chemical bond
  • R 1 is cyano or nitro
  • R 2 is hydrogen, fluorine, chlorine, C 1 -C 2 -alkyl, ethenyl or C 1 -C 2 -alkoxy;
  • R 3 is fluorine or hydrogen; R 4 is methyl;
  • R 5 is hydrogen, methyl or ethyl
  • R 6 is hydrogen, methyl, or ethyl
  • R 7 is hydrogen or halogen; and at least one further active ingredient selected from B) herbicides of classes b1) to b15): b1) lipid biosynthesis inhibitors; b2) acetolactate synthase inhibitors (ALS inhibitors); b3) photosynthesis inhibitors; b4) protoporphyrinogen IX oxidase inhibitors, b5) bleacher herbicides; b6) enolpyruvyl-shikimate-3-phosphate synthase inhibitors (EPSP inhibitors); b7) glutamine synthetase inhibitors; b8) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors); b9) mitosis inhibitors; b10) inhibitors of long-chain fatty acid synthesis (VLCFA inhibitors); b11) cellulose biosynthesis inhibitors; b12) decoupling herbicides; b13) auxin herbicides; b14) auxin transport inhibitors; and b15) other herbicides selected from
  • the invention relates to compositions in the form of herbicidally active crop protection compositions comprising a herbicidally effective amount of a combination of active substances comprising at least one piperazinedione compound A and at least one further compound selected from herbicides B and safeners C, as defined above, and at least one liquid and or solid carrier and / or one or more surface-active substances and, if desired, one or more further auxiliaries customary for crop protection agents.
  • the invention also relates to compositions in the form of a 1-
  • Component composition formulated crop protection agent containing a combination of active substances comprising at least one piperazinedione compound of formula I and at least one other active ingredient selected from herbicides B and safeners C, and at least one solid or liquid carrier and / or one or more surface-active substances and if desired, one or more further auxiliaries customary for pesticides.
  • the invention also relates to compositions in the form of a plant protection composition formulated as a 2-component composition, comprising a first component containing at least one piperazinedione compound of the formula I, a solid or liquid carrier and / or one or more surface-active substances, and a second component containing at least one further active ingredient, selected from herbicides B and safeners C, a solid or liquid carrier and / or one or more surface-active substances, it being additionally possible for both components to comprise other auxiliaries customary for crop protection agents.
  • a plant protection composition formulated as a 2-component composition, comprising a first component containing at least one piperazinedione compound of the formula I, a solid or liquid carrier and / or one or more surface-active substances, and a second component containing at least one further active ingredient, selected from herbicides B and safeners C, a solid or liquid carrier and / or one or more surface-active substances, it being additionally possible for both components to comprise other auxiliaries customary for crop protection agents.
  • compositions according to the invention which contain at least one piperazinedione compound of the general formula I and at least one herbicide B have Surprisingly, a better herbicidal effectiveness, ie a better action against harmful plants than would have been expected due to the herbicidal activity observed for the individual compounds, or a broader spectrum of activity.
  • the herbicidal effect to be expected for mixtures due to the single compound can be calculated by the Colby formula (see below). If the observed effect exceeds the expected additive effect of the individual compounds, one speaks of the presence of a synergism.
  • compositions according to the invention which contain both at least one piperazinedione compound of the general formula I and a herbicide B and optionally a safener C, increase the time window within which the desired herbicidal action can be achieved. This allows a more flexible temporal use of the compositions of the invention compared to the individual compounds.
  • compositions according to the invention which contain both at least one piperazinedione compound of the general formula I and at least one of the compounds mentioned under C, likewise have a good herbicidal action against harmful plants and a better crop tolerance.
  • compositions according to the invention which contain at least one piperazinedione compound of the general formula I, at least one herbicide B and contain at least one of the compounds mentioned under C, surprisingly have a better herbicidal efficacy, i. H. a better activity against harmful plants than would have been expected due to the herbicidal activity observed for the individual compounds, or a broader spectrum of activity and show a better tolerance to crops than compositions containing only a compound I and a herbicide B.
  • the invention further relates to a method for controlling undesired plant growth, in particular in cultivated areas of crop plants, for example in crops of the following crop plants: Allium cepa, pineapple comosus, Arachis hypogea, Asparagus officinalis, Avena sativa, Beta vulgaris spec. altissima, Beta vulgaris spec. rapese, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var.
  • Pistacia vera Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca, Prunus cerasus, Prunus dulcis and Prunus domestica, Ribes sylvestre, Ricinus communis, Sac Charum officinarum, Seeale cereale, Sinapis alba, Solanum tuberosum, Sorghum bicolor (see vulgaris), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Vicia faba, Vitis vinifera, Zea mays, especially cereal, maize, soybean, rice, rapeseed, cotton, Potato, peanut or permanent crops, as well as in crops that are resistant to one or more herbicides or infestation by insects due to genetic engineering or breeding measures.
  • the invention also relates to a method for desiccation or defoliation of plants.
  • the organic parts of the molecule mentioned in the definition of the substituents R 1 to R 7 in formula I - like the meaning of halogen - are collective terms for individual enumerations of the individual group members.
  • the prefix C n -Cm indicates in each case the possible number of carbon atoms in the group , Accordingly, d-C2-alkyl is methyl or ethyl.
  • Ci-C2-alkoxy is methoxy or ethoxy.
  • Aryl represents mononuclear or polynuclear aromatic hydrocarbon radicals having 6 to 14 carbon atoms, such as phenyl, naphthyl, anthracenyl or phenanthrenyl, preferably phenyl or naphthyl.
  • the composition as an active ingredient or component A contains at least one compound of formula I, wherein R x and R y in formula I are together a covalent bond.
  • R x and R y in formula I are together a covalent bond.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 have the meanings given above.
  • R 3 in formula Ia is fluorine
  • R 3 is in particular in the ortho position to the group R 2 .
  • R 7 is halogen
  • R 7 is located in the para position to the phenyl ring binding site.
  • compounds of the formula Ia are also preferred in which R 7 is located in the meta position to the binding site of the phenyl ring.
  • Compounds of the formula Ia in which R 3 is arranged in the ortho position to the group R 2 and R 7 in the meta or para position to the binding site of the phenyl ring are also referred to below as compounds Iaa.
  • compositions containing as component A at least one compound Ia preference is given to those compositions in which the compound of formula Ia is in the form of the (Z) isomer or in the form of a mixture of Z and E isomers, predominantly the Z. Isomer is present.
  • these include, in particular the pure Z isomer and isomer mixtures having an E / Z ratio of not more than 1: 2, in particular not more than 1: 5 are preferred.
  • the compounds of the formula I have a center of chirality on the carbon atom which carries the group R 6 .
  • a preferred embodiment of the invention relates to the pure enantiomers of the formula Ia-S below, in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 have one of the meanings given above, in particular one of the following have as preferred or as particularly preferred meanings, as well as enantiomeric mixtures having an enantiomeric excess with respect to the enantiomer of the formula Ia-S.
  • R 3 in the formula Ia-S is fluorine
  • R 3 is located in the ortho position to the group R 2 .
  • R 7 is halogen
  • R 7 is in particular in the para position to the binding site of the phenyl ring.
  • R 7 is halogen
  • particular preference is also given to compounds of the formula Ia-S in which R 7 is located in the meta position relative to the binding site of the phenyl ring.
  • Compounds of formula Ia-S, wherein R 3 are arranged in the ortho-position to the group R 2 and R 7 in the meta or para position to the binding site of the phenyl ring are hereinafter also referred to as compounds I.aa-S.
  • Enantiomeric excess preferably means an ee value (enantiomeric ex- cess) of at least 70%, in particular at least 80% and especially at least 90%. Also preferred are the agriculturally suitable salts of the enantiomers I.a-S and enantiomeric mixtures of the salts having an enantiomeric excess with respect to the enantiomer of the formula I.a-S.
  • compositions which contain as active ingredient or component A a racemic mixture of at least one compound I.a-S with its optical antipode I.a-R.
  • the composition contains as component A at least one compound of formula I, wherein R x and R y in formula I are each hydrogen. These compounds are also referred to below as compounds 1b.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 have the meanings given above.
  • R 3 in formula Ib is fluorine
  • R 3 is in particular in the ortho position to the group R 2 .
  • R 7 is halogen
  • R 7 is located in the para position to the phenyl ring binding site.
  • R 7 is halogen
  • particular preference is also given to compounds of the formula Ib in which R 7 is located in the meta position to the binding site of the phenyl ring.
  • Compounds of the formula Ib in which R 3 is arranged in the ortho position to the group R 2 and R 7 in the meta or para position to the point of attachment of the phenyl ring are also referred to below as compounds 1 bb.
  • the compounds of the formula Ib have in each case one chiral center on the carbon atoms of the 3 and 6 positions of the piperazine ring. Preference is given to those compounds of the formula Ib in which the benzylic groups at the 3- and the 6-position have a cis arrangement with respect to the piperazine ring, ie the S, S-enantiomer (S 1 S) -Lb and the R, R- Enantiomer (R 1 R) -Lb and mixtures thereof.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 have the meanings given above.
  • R 3 in the formula Lb is fluorine
  • R 3 is located in the ortho position to the group R 2 .
  • R 7 is especially arranged in the para position to the binding site of the phenyl ring.
  • R 7 is also located in the meta position to the phenyl ring binding site.
  • a particularly preferred embodiment of the invention relates to compositions which contain, as component A, the S, S-enantiomer of the formula (S 1 S) -Lb, as well as enantiomeric mixtures and diastereomeric mixtures of Lb, in which the S, S-enantiomer is the main constituent and preferably at least 70 %, in particular at least 80% and especially at least 90% of compound I. Also preferred are the agriculturally suitable salts of the enantiomers (S 1 S) -Lb and mixtures of enantiomers and diastereomeric mixtures of the salts wherein the S, S enantiomer is major and preferably at least 70%, more preferably at least 80% and especially at least 90% of the compound I. accounts.
  • Another, equally preferred embodiment relates to compositions comprising as component A a racemic mixture of the S, S-enantiomer (S 1 S) -Lb with the R, R-enantiomer (R 1 R) -Lb.
  • R 6 is hydrogen. According to a further preferred embodiment, R 6 is methyl or ethyl.
  • R 2 hydrogen, fluorine, chlorine, methyl or methoxy, in particular hydrogen,
  • R 3 hydrogen or fluorine
  • R 7 hydrogen or fluorine.
  • Preferred compounds of the formula I which are part of the composition according to the invention as component A are the compounds 1-1 to 1-102 listed below, in particular their Z isomers and especially the Z isomers, wherein the carbon is in the 6-position of the piperazine ring S configuration.
  • Preferred compounds of the formula I which are part of the composition according to the invention as component A are furthermore the compounds 1-103 to 1-146 listed below, in particular their cis isomers and especially their S, S isomers.
  • Compound A Compound 1-1, i. 2- [5-Benzyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylidenemethyl] -benzonitrile.
  • the composition as compound A contains the compound 1-21, i. 2- [5-Benzyl-1, 4,5-trimethyl-3,6-dioxopiperazin-2-ylidenemethyl] benzonitrile.
  • the composition as compound A contains compound 1-103, i. 2- [5-Benzyl-1, 4,5-trimethyl-3,6-dioxopiperazin-2-ylmethyl] -benzonitrile.
  • R 2 , R 3 , R 6 and R 7 have the meanings given above.
  • L is halogen, e.g. B bromine, CN or nitro.
  • Pg is a nitrogen protecting group, eg an acetyl radical.
  • R is hydrogen or a protective group Pg.
  • step a) a substituted benzaldehyde compound III is reacted under the conditions of an aldol condation with an N-protected piperazine-2,5-dione compound IV benzylated in the 3-position.
  • the aldol condensation is typically carried out in the presence of suitable bases.
  • suitable bases are those which are commonly used in aldol condensations.
  • an alkali metal or alkaline earth metal carbonate is used as the base, e.g. Sodium carbonate, potassium carbonate or cesium carbonate or mixtures thereof.
  • the reaction is carried out in an inert, preferably aprotic organic solvent.
  • suitable solvents are in particular dichloromethane, dichloroethane, chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, and dimethyl sulfoxide, dimethylformamide, N-methylpyrrolidone and dimethylacetamide.
  • Preferred solvents are selected in particular from dimethylformamide, N-methylpyrrolidone and dimethylacetamide.
  • the temperatures required for the aldol condensation are generally in the range from 0 ° C. up to the boiling point of the solvent used and in particular in the range from 10 to 80 ° C.
  • an N-protected compound V is obtained.
  • the spin-off the (remaining) protecting group (s) in step b) can be carried out analogously to standard methods of protecting group chemistry, for example according to the Green, Wuts, Protective Groups in Organic Synthesis, 3rd ed. 1999, John Wiley and Sons, p. 553 ff. described method.
  • the compound of formula VI thus obtained is then added to
  • the piperazine compound of the formula VI is l michsvon according to common alkylation, as for example from Heterocycles, 45, 1997, 1151 and Chem. Commun. 1998, 659 are reacted with a suitable alkylating agent of the formula X 1 -R 4 and optionally an alkylating agent X 1 -R 5 implemented.
  • X 1 may be halogen or O-SO 2 -R m with R m meaning Ci-C 4 -alkyl or aryl, which may be halogen, CrC 4 -AlkVl or halo-Ci-C 4 - alkyl substituted mean.
  • R 4 and R 5 independently of one another are methyl, methyl or ethyl. If R 4 and R 5 are not identical, the alkylation steps are carried out successively. When R 4 and R 5 are identical, the alkylation steps can be carried out simultaneously or successively in any order.
  • the alkylation of VI is usually carried out at temperatures in the range from -78 ° C to the boiling point of the reaction mixture, preferably from -50 0 C to 65 ° C, particularly preferably from -30 0 C to 65 ° C.
  • the reaction is carried out in a solvent, preferably in an inert organic solvent.
  • Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-Al kanen, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as dichloromethane, dichloroethane, chloroform and chlorobenzene, ethers such as diethyl ether , Diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, ter
  • Preferred solvents are toluene, dichloromethane, tetrahydrofuran, N-methylpyrrolidone or dimethylformamide and mixtures thereof.
  • Suitable bases are inorganic compounds such as alkali metal and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide or calcium hydroxide, aqueous solution of ammonia, alkali metal or alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and Calcium hydride, alkali metal amides such as lithium amide, for example lithium diisopropylamide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates such as lithium carbonate, potassium carbonate, cesium carbonate and calcium carbonate, and alkali metal bicarbonates such as sodium bicarbonate, organometallic acid.
  • alkali metal and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide or calcium hydroxide
  • aqueous solution of ammonia alkali metal or alka
  • alkali metal alkyls such as methyllithium, butyllithium and phenyllithium
  • alkylmagnesium halides such as methylmagnesium chloride and alkali metal and alkaline earth metal such as sodium, sodium, potassium methoxide, potassium tert-butoxide, potassium tert-pentoxide and dimethoxy magnesium
  • organic bases eg tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine, 2-hydroxypyridine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine, and bicyclic amines.
  • the bases are generally used equimolar. They can also be used in excess or even as a solvent. In a preferred embodiment, the base is added in equimolar amount or substantially equimolar amount. In another preferred embodiment, sodium hydride is used as the base.
  • R 6 in formula VI is hydrogen
  • a methyl or ethyl group can be introduced as the radical R 6 by reaction with an alkylating agent R 6 -X 1 .
  • R 6 -X 1 In the alkylating agent R 6 -X 1 , X 1 has one of the abovementioned meanings.
  • R 6 is methyl or ethyl.
  • the alkylation can be carried out by standard methods, as described, for example, in J. Am. Chem. Soc. 105, 1983, 3214 are described. If the radicals R 4 , R 5 and R 6 are identical, it is possible to introduce all 3 groups simultaneously or successively by alkylation, with the piperazine nitrogens generally being first alkylated.
  • L is a halogen atom, for example chlorine, bromine or iodine
  • a nitrile group can be introduced in step d).
  • the compound La in which L is chlorine, bromine or iodine can be reacted with copper cyanide in analogy to known processes (see, for example, Organikum, 21st edition, US Pat. 2001, Wiley, p 404, Tetrahedron Lett 42, 2001, p 7473 or Org. Lett 5, 2003, 1785 and literature cited therein). These reactions are usually carried out at temperatures in the range of 100 0 C to the boiling point of the reaction mixture, preferably from 100 0 C to 250 0 C.
  • reaction is carried out in an inert organic solvent.
  • suitable solvents are, in particular, aprotic polar solvents, for example dimethylformamide, N-methylpyrrolidone, N, N'-dimethylimidazolidin-2-one and dimethylacetamide.
  • the compound of formula La can then be hydrogenated to compound Lb.
  • the hydrogenation is carried out by reaction with hydrogen in the presence of transition metal catalysts, for example catalysts containing Pt, Pd, Rh or Ru as active metal species.
  • Suitable catalysts are both heterogeneous catalysts such as Pd or Pt supported catalysts, eg Pd on activated charcoal, furthermore PtC 2, and also homogeneous catalysts. Active catalysts allows enantioselective hydrogenation of the double bond (see Peptide Chemistry 17, 1980, pp. 59-64, Tetrahedron Lett. 46, 1979, pp. 4483-4486).
  • the hydrogenation of Ia may occur both after the alkylation of VI, i. after step c) or d), as well as before the alkylation i. after step b).
  • the aldehyde III is either commercially available or can be synthesized according to known methods for the preparation of aldehydes.
  • the compounds of the formula IV can be prepared by intramolecular cyclization of compounds of the general formula VII and subsequent introduction of protective groups Pg into the compound VIII thus obtained.
  • R 6 and R 7 have the meanings given above.
  • R x is, for example, C 1 -C 6 -alkyl, in particular methyl, ethyl or phenyl-d-ce-alkyl, for example benzyl.
  • step f) The cyclization of VII in step f) can be carried out in analogy to other methods known from the literature, for example according to T. Kawasaki et al., Org. Lett. 2 (19) (2000), 3027-3029, Igor L. Rodionov et al., Tetrahedron 58 (42) (2002), 8515-8523 or AL Johnson et al., Tetrahedron 60 (2004), 961-965 respectively.
  • step g) suitable protecting groups Pg are then introduced into the compound VIII.
  • the introduction of the protective groups into the compound VIII can be carried out in analogy to known methods of protecting group chemistry, for example by reacting the corresponding NH-free compound VIII with anhydrides of the formula (R 52 C (O)) 2 O, where R 52 is C 1 -C 4 4 -alkyl, for example methyl, for example, according to the method described in Green, Wuts, Protective Groups in Organic Synthesis, 3rd ed. 1999, John Wiley and Sons, p. 553.
  • the compounds of formula VII are in turn known and can by
  • the compositions contain at least one inhibitor of lipid biosynthesis (herbicide b1). These are compounds that inhibit lipid biosynthesis. This inhibition may be due to inhibition of acetyl CoA carboxylase (hereinafter also referred to as ACC herbicides) or to another mechanism (also referred to below as non-ACC herbicides).
  • ACC herbicides belong to group A of the HRAC classification
  • group N non-ACC herbicides belong to the HRAC classification.
  • the compositions contain at least one ALS inhibitor (herbicide b2).
  • ALS inhibitor are compounds whose herbicidal action is based on the inhibition of acetolactate synthase and thus on the inhibition of the branched-chain amino acid biosynthesis.
  • Such inhibitors belong to group B of the HRAC classification.
  • the compositions contain at least one photosynthesis inhibitor (herbicide b3).
  • photosynthesis inhibitors are compounds whose herbicidal action on the inhibition of the photosystem II in plants (so-called PSII inhibitors, groups C1, C2 and C3 of the HRAC classification) or on the obstruction of the electron transfer in the photosystem I of the plants (so-called. PSI inhibitors, group D of HRAC classification) and thus based on inhibition or disruption of photosynthesis. Of these, PSII inhibitors are preferred.
  • the compositions contain at least one protoporphyrinogen IX oxidase inhibitor (herbicide b4).
  • protoporphyrinogen IX oxidase inhibitor herebicide b4
  • These are compounds whose herbicidal action is based on the inhibition of protoporphyrinogen IX oxidase.
  • Such inhibitors belong to group E of the HRAC classification.
  • the compositions contain at least one bleacher herbicide (herbicide b5).
  • bleacher herbicide are compounds whose herbicidal action is based on the inhibition or disruption of carotenoid biosynthesis.
  • PDS inhibitors compounds which prevent carotenoid biosynthesis by inhibiting the phytoene desaturase
  • HPPD inhibitors compounds which inhibit 4-hydroxyphenylpyruvate dioxygenase
  • compounds which inhibit carotenoid biosynthesis in a manner not yet clarified (Bleacher - unknown target, class F3 of the HRAC classification).
  • the compositions contain at least one EPSP synthase inhibitor (herbicide b6). These are compounds whose herbicidal action is based on the inhibition of enolpyruvyl-shikimate-3-phosphate synthase and thus on the inhibition of the biosynthesis of amino acids in plants. Such inhibitors belong to group G of the HRAC classification.
  • the compositions contain at least one glutamine synthetase inhibitor (herbicide b7). These are compounds whose herbicidal action is based on the inhibition of glutamine synthetase and thus also on the inhibition of the biosynthesis of amino acids in plants. Such inhibitors belong to group H of the HRAC classification.
  • the compositions contain at least one DHP synthase inhibitor (herbicide b8).
  • DHP synthase inhibitor herebicide b8
  • These are compounds whose herbicidal action is based on the inhibition of 7,8-dihydropteroate synthase.
  • Such inhibitors belong to group I of the HRAC classification.
  • the compositions contain at least one mitosis inhibitor (herbicide b9).
  • mitosis inhibitors are compounds whose herbicidal action is based on the disturbance or inhibition of the production or organization of the microtubules and thus inhibits mitosis.
  • Such inhibitors belong to groups K1 and K2 of the HRAC classification. Of these, preference is given to compounds of the group K1, in particular dinitroanilines.
  • the compositions contain at least one VLCFA inhibitor (herbicide b10).
  • VLCFA inhibitor herebicide b10
  • These are compounds whose herbicidal action is based on the inhibition of the synthesis of long-chain fatty acids and thus on a disruption or inhibition of cell division in plants.
  • Such inhibitors belong to group K3 of the HRAC classification.
  • the compositions contain at least one cellulose biosynthesis inhibitor (herbicide b11).
  • cellulose biosynthesis inhibitor herebicide b11
  • Such inhibitors belong to group L of the HRAC classification.
  • the compositions contain at least one decoupling herbicide (herbicide b12). These are compounds whose herbicidal action is based on the destruction of the cell membrane. Such inhibitors belong to group M of the HRAC classification.
  • the compositions contain at least one auxin herbicide (herbicide b13).
  • auxin herbicide are compounds that act as auxins, ie phytohormones in plants, and inhibit the growth of plants.
  • auxins ie phytohormones in plants, and inhibit the growth of plants.
  • Such substances belong to group O of the HRAC classification.
  • the compositions contain at least one auxin transport inhibitor (herbicide b14).
  • auxin transport inhibitor herein transport inhibitors
  • These are compounds whose herbicidal activity is based on the inhibition of xintransport in plants.
  • Such substances belong to group P of the HRAC classification.
  • HRAC Classification of Herbicides According to Mode of Action
  • http://www.plantprotection.org/hrac/MOA.html For the reported modes of action and classification of drugs, see eg "HRAC, Classification of Herbicides According to Mode of Action", http://www.plantprotection.org/hrac/MOA.html).
  • compositions according to the invention are those which contain at least one herbicide B selected from the herbicides of the classes b1), b2), b3), M), b5), b9), b10, b1 1) and b13).
  • a particularly preferred embodiment of the invention relates to compositions containing at least one herbicide B selected from the class b10 herbicides.
  • herbicides B that can be used in combination with the piperazinedione compounds of the formula I according to the present invention are: b1) from the group of lipid biosynthesis inhibitors:
  • ACC herbicides such as alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofopmethyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, Fluazifop, Fluazifop-butyl, Fluazifop-P, Fluazifop-P-butyl, Haloxyfop, Haloxyfop-methyl, Haloxy-fop-P, Haloxyfop-P-methyl, Metamifop, Pinoxaden, Profoxydim, Propaquizafop, Quizalofop, Quizalofop-ethyl, Quiz
  • Triazolopyrimidine herbicides and sulfonamides such as cloransulam, cloransulam-methyl,
  • Pyrimdinylbenzoate as Bispyribac, Bispyribac sodium, Pyribenzoxim, Pyriftalid, Pyriminobac, Pyriminobac-methyl, Pyrithiobac, Pyrithiobacsodium, and
  • Sulfonylaminocarbonyltriazolinone herbicides such as flucarbazone, flucarbazone sodium, propoxycarbazone, propoxycarbazone sodium, thiencarbazone and thiencarbazone methyl.
  • compositions containing at least one imidazolinone herbicide are a preferred embodiment of the invention; b3) from the group of photosynthesis inhibitors:
  • Amicarbazone, photosystem II inhibitors e.g. Triazine herbicides including chlorotriazines, triazinones, triazinediones, methylthiotriazines and pyridazinones such as ametryn, atrazine, chloridazon, cyanazine, desmetryn, dimethametryn, hexazinone, metribuzin, prometon, prometryn, propazine, simazine, simetryn, terbumetone, terbuthylazine, terbutryn and trietazine , Aryl ureas such as chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isourone, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, siduron,
  • Uracils such as bromacil, lenacil and terbacil, as well as bentazone and bentazone sodium, pyridatre, pyridafol, pentanochlor and propanil, and inhibitors of phostosystem I such as diquat, diquat-dibromide, paraquat, paraquat-dichloride and paraquat-dimetilsulfat.
  • compositions containing at least one triazine herbicide also constitute a preferred embodiment of the invention.
  • compositions containing at least one nitrile herbicide constitute a preferred embodiment of the invention; b4) from the group of protoporphyrinogen IX oxidase inhibitors:
  • HPPD inhibitors benzobicyclone, benzofenap, isoxaflutole, mesotrione, pyrasulfotol, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, topramezone, 4-
  • Bilanaphos (bialaphos), bilanaphos-sodium, glufosinate and glufosinate-ammonium; b8) from the group of DHP synthase inhibitors:
  • Ethalfluralin Fluchloralin, Oryzalin, Pendimethalin, Prodiamin and Trifluralin, Phosphoramidates like Amiprophos, Amiprophos-methyl and Butamiphos, benzoic acids like
  • Chlorthal chlorothal-dimethyl
  • pyridines such as dithiopyr and thiazopyr
  • benzamides such as propyzamide and tebutam
  • Compounds of group K2 chlorpropham, propham and carbethamide.
  • Oxyacetanilides such as flufenacet and mefenacet
  • Acetanilides such as diphenamid, naproanilide and napropamide, tetrazolinones such as fentrazamide, and others such as anilofos, cafenstrol, piperophos, pyroxasulfone and isoxazoline compounds of formula II other than pyroxasulfone,
  • R 1, R 2 , R 3 , R 4 , X, Y and n have the following meanings: R 1, R 2 , R 3 , R 4 are each independently of one another hydrogen, halogen or C 1 -C 4 -alkyl;
  • Y is phenyl or monocyclic 5-, 6-, 7-, 8-, 9- or 10-membered heterocyclyl containing in addition to carbon ring members one, two or three identical or different heteroatoms selected from the group oxygen, sulfur or Nitrogen as ring members, wherein phenyl and heterocyclyl are unsubstituted or carry 1, 2 or 3 substituents Rw, which are selected from halogen, -C 4 - alkyl, d-C4-alkoxy, Ci-C4-haloalkyl and Ci-C4-haloalkoxy, preferably Phenyl or 5- or 6-membered aromatic heterocyclyl (hetaryl) which contains, in addition to carbon ring members, one, two or three nitrogen atoms as ring members, where phenyl and hetaryl are unsubstituted or have 1, 2 or 3 substituents R yy ,
  • X is oxygen or NH; and n is zero or one.
  • the isoxazoline compounds of the formula II are the isoxazoline compounds of the formula II.
  • R 1, R 2, R 3, R 4 each independently represent H, F, Cl or methyl
  • X is oxygen; n is 0 or 1; and
  • Y is phenyl, pyrazolyl or 1, 2,3-triazolyl, where the last three radicals are unsubstituted or carry one, two or three substituents Rw, especially one of the following radicals:
  • R 5 is halo, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl
  • R 6 is C 1 -C 4 -alkyl
  • R7 is halo, -C 4 -alkoxy or Ci-C4-haloalkoxy;
  • Rs is halogen, Ci-C4-alkyl, Ci-C4-haloalkyl or Ci-C is 4 -haloalkoxy;
  • m is 0, 1, 2 or 3;
  • # denotes the link to the group CR3R4.
  • R-i is hydrogen
  • R 2 is fluorine
  • R3 is hydrogen or fluorine
  • R 4 is hydrogen or fluorine; X is oxygen; n is zero or 1, in particular 1; and
  • Y is one of the radicals of the formulas Yi, Y2, Y3 or Y 4 ,
  • the isoxazoline compounds of the formula II are known from the literature, for. From WO 2006/024820, WO 2006/037945, WO 2007/071900 and WO 2007/096576.
  • VLCFA inhibitors preferred are chloroacetamides, oxyacetamides and pyroxasulfone; b11) from the group of cellulose biosynthesis inhibitors: chlorthiamide, dichlobenil, flupoxam and isoxaben; b12) from the group of decoupling herbicides:
  • Acetochlor alachlor, anilofos, butachlor, cafenstrol, dimethenamid, dimethenamid-P, fentrazamide, flufenacet, mefenacet, metazachlor, metolachlor, S-metolachlor, naproanilide, napropamide, pretilachlor, pyroxasulfone, thenylchlor and isoxazoline compounds of the formulas 11.1, II .2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9
  • aminopyralid and its salts such as aminopyralidtris (2-hydroxypropyl) ammonium and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop-P and its salts and Esters, fluoroxypyr-meptyl, MCPA and its salts and esters, MCPB and its salts and esters,
  • Mecoprop-P and its salts and esters, picloram and its salts and esters, quinoline rac, quinmerac, triclopyr and its salts and esters, and 5,6-dichloro-2-cyclopropyl-4-pyrimidinecarboxylic acid (CAS 858956-08-8) and its salts and esters; b14) from the group of auxin transport inhibitors: diflufenzopyr and diflufenzopyr sodium; b15) from the group of the other herbicides: bromobutide, cinmethylin, cumyluron, dalapon, difenzoquat, difenzoquat-methylsulfate, DSMA, dymron ( daimurone), flamprop, flampropisopropyl, flampropymethyl, flamprop-M-isopropyl, flamprop -M-methyl, indanofane, metam, methylbromide, MSMA, oxazi
  • herbicides B which can be used in combination with the piperazinedione compounds of the formula I according to the present invention are: b1) from the group of the lipid biosynthesis inhibitors: clodinafop-propargyl, cyclopydim, cyhalofop-butyl, Fenoxaprop-P-ethyl, pinoxaden, profoxydim, tepraloxydim, tralkoxydim, esprocarb, prosulfocarb, thiobencarb and triallate; b2) from the group of ALS inhibitors: Bensulfuron-methyl, Bispyribac sodium, Cyclosulfamuron, Flumetsulam, Flupyrsulfuron-methyl-Sodium, Foramsulfuron, Imazamox, Imazapic, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Iodosulfuron, Iodosulfuron-methyl
  • Preferred safeners C are Benoxacor, Cloquintocet, Cyprosulfamide, Dichlormid,
  • Particularly preferred safeners C are Benoxacor, Cloquintocet, Cyprosulfamide,
  • the active compounds B of groups b1) to b15) and the active compounds C are known herbicides and safeners, see, for example, US Pat. B. The Compendium of Pesticide Common Names (http://www.alanwood.net/pesticides/); Farm Chemicals Handbook 2000 Volume 86, Meister Publishing Company, 2000; Hock, C. Fedtke, R.R. Schmidt, Herbicides, Georg Thieme Verlag, Stuttgart 1995; W.H. Ahrens, Herbicide Handbook, 7th Edition, Weed Science Society of America, 1994; and K.K. Hatzios, Herbicide Handbook, Supplement to the 7th Edition, Weed Science Society of America, 1998.
  • the assignment of the active ingredients to the respective mechanisms of action is based on the current state of knowledge. If more than one mode of action is involved for an active substance, then this substance has been assigned to only one mechanism of action.
  • herbicides B and / or safeners C geometric isomers, eg. B. E / Z can form isomers, both the pure isomers and their mixtures can be used in the compositions of the invention. If the herbicides B and / or the safeners C have one or more chiral centers and are therefore present as enantiomers or diastereomers, both the pure enantiomers and diastereomers and mixtures thereof can be used in the compositions according to the invention.
  • the herbicides B and / or the safeners C have ionizable functional groups, they can also be used in the form of their agriculturally acceptable salts.
  • the salts of those cations or the acid addition salts of those acids come into consideration whose cations, or anions, the effect of the active ingredients do not adversely affect.
  • Preferred cations are the ions of the alkali metals, preferably lithium, sodium and potassium, the alkaline earth metals, preferably calcium and magnesium, and the transition metals, preferably manganese, copper, zinc and iron, further ammonium and substituted ammonium wherein one to four hydrogen atoms are replaced by C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, phenyl or benzyl, preferably ammonium , Methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogen sulfate, methyl sulfate, sulfate, dihydrogen phosphate,
  • Such active substances B and C which have a carboxyl group, can be used in the form of the acid, in the form of an agriculturally suitable salt but also in the form of an agriculturally acceptable derivative in the compositions according to the invention, e.g. as amides, such as mono- and di-C 1 -C 6 -alkylamides or arylamides, as esters, e.g. allyl esters, propargyl esters, C 1 -C 10 -alkyl esters, alkoxyalkyl esters and thioesters, e.g. be used as Ci-Cio-alkylthioester.
  • Preferred mono- and di-C 1 -C 6 -alkylamides are the methyl and the dimethylamides.
  • Preferred arylamides are, for example, the anilides and the 2-chloroanilides.
  • Preferred alkyl esters are, for example, the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1-methylhexyl) or isooctyl (2-ethylhexyl) esters.
  • C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl esters are the straight-chain or branched C 1 -C 4 -alkoxyethyl esters, for example the methoxyethyl, ethoxyethyl or butoxyethyl esters.
  • An example of the straight-chain or branched C 1 -C 10 -alkyl thioesters is the ethylthioester.
  • a first preferred embodiment of the invention relates to compositions according to the invention which, in addition to a piperazinedione compound of the formula I, especially an active compound from the group 1-1 to 1-146, at least one and especially precisely one herbicidal active compound from the group b1), in particular Clodina-opopargyl, Cycloxydim, Cyhalofop-butyl, Fenoxaprop-P-ethyl, Pinoxaden, Profox dim, Tepraloxydim, Tralkoxydim, Esprocarb, Prosulfocarb, Thiobencarb and Triallat included.
  • a piperazinedione compound of the formula I especially an active compound from the group 1-1 to 1-146, at least one and especially precisely one herbicidal active compound from the group b1), in particular Clodina-opopargyl, Cycloxydim, Cyhalofop-butyl, Fenoxaprop-P-ethyl, Pinoxaden, Profox dim
  • a second preferred embodiment of the invention relates to compositions according to the invention which, in addition to a piperazinedione compound of the formula I, especially one active compound from the group 1-1 to 1-146, at least one and especially exactly one herbicidal active substance from the group b2), in particular under Bensul furon-methyl, bispyribac sodium, cyclosulfamuron, flumetsulam, flupyrsulfuron methylsodium, foramsulfuron, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, lodosulfuron, lodosulfuron methylsodium, mesosulfuron, nicosulfuron, penoxsulam, propoxycarbazone sodium, pyrazosulfuron-ethyl, pyroxsulfame, rimsulfuron, sulfosulfuron, thiencarbazone-methyl, and tri
  • a third preferred embodiment of the invention relates to compositions according to the invention which, in addition to a piperazinedione compound of the formula I, especially an active compound from the group 1-1 to 1-146, at least one and especially exactly one herbicidal active substance from the group b3), in particular selected from atrazine , Diuron, fluometuron, hexazinone, isoproturon, metribuzin, paraquat, paraquat dichloride, propanil and terbuthylazine.
  • a piperazinedione compound of the formula I especially an active compound from the group 1-1 to 1-146, at least one and especially exactly one herbicidal active substance from the group b3), in particular selected from atrazine , Diuron, fluometuron, hexazinone, isoproturon, metribuzin, paraquat, paraquat dichloride, propanil and terbuthylazine.
  • a fourth preferred embodiment of the invention relates to compositions according to the invention which, in addition to a piperazinedione compound of the formula I, especially an active compound from the group 1-1 to 1-146, at least one and especially exactly one herbicidal active compound from the group b4), in particular with flumioxazine, oxyfluorfen, sulfentrazone, 2-chloro-5- [3,6-dihydro-3-methyl-2,6-dioxo-4- (trifluoromethyl) -1 (2H) -pyrimidinyl] -4-fluoro- N - [(isopropyl) methylsulfamoyl] benzamide (CAS 372137-35-4) and [3- [2-chloro-4-fluoro-5- (1-methyl-6-trifluoromethyl-2,4-dioxo-1,2-d , 3,4-tetrahydropyrimidin-3-yl) phenoxy] -2-pyridyloxy]
  • a fifth preferred embodiment of the invention relates to compositions according to the invention which, in addition to a piperazinedione compound of the formula I, especially an active compound from the group 1-1 to 1-146, at least one and especially exactly one herbicidal active compound from the group b5), in particular selected from Cloma - zon, diflufenican, flurochloridone, isoxaflutole, mesotrione, picolinafen, sulcotrione, tefuryltrione, tembotrione, topramezone and 4-hydroxy-3 - [[2 - [(2-methoxyethoxy) methyl] -6- (trifluoromethyl) -3- pyridyl] carbonyl] bicyclo [3.2.1] oct-3-en-2-one (CAS 352010-68-5).
  • a piperazinedione compound of the formula I especially an active compound from the group 1-1 to 1-146, at least one and especially exactly one herbicidal active compound
  • a sixth preferred embodiment of the invention relates to compositions according to the invention which, in addition to a piperazinedione compound of the formula I, especially an active compound from the group 1-1 to 1-146, at least one and especially exactly one herbicidal active compound from the group b6), in particular among glyphosate, glyphosate isopropylammonium and glyphosate trimesium (sulfosate).
  • a seventh preferred embodiment of the invention relates to the invention
  • compositions which, in addition to a piperazinedione compound of the formula I, especially an active compound from the group 1-1 to 1-146, contain at least one and especially exactly one herbicidal active substance from the group b7), in particular selected from glufosinate and glufosinate-ammonium.
  • An eighth preferred embodiment of the invention relates to the invention
  • compositions which, in addition to a piperazinedione compound of the formula I, especially an active compound from the group 1-1 to 1-146, at least one and especially exactly one herbicidally active compound from group b9), in particular selected from pendenthalin and trifluralin.
  • a ninth preferred embodiment of the invention relates to compositions according to the invention which, in addition to a piperazinedione compound of the formula I, especially an active compound from the group 1-1 to 1-146, at least one and especially exactly one herbicidal active compound from the group b10), in particular acetoacetate, cafenstrol, dimethenamid-P, fentrazamide, flufenacet, mefenacet, metazachlor, S-metolachlor and pyroxasulfone.
  • a piperazinedione compound of the formula I especially an active compound from the group 1-1 to 1-146, at least one and especially exactly one herbicidal active compound from the group b10), in particular acetoacetate, cafenstrol, dimethenamid-P, fentrazamide, flufenacet, mefenacet, metazachlor, S-metolachlor and pyroxasulfone.
  • compositions which, in addition to a piperazinedione compound of the formula I, especially an active compound from the group 1-1 to 1-146, at least one and especially exactly one herbicidal active ingredient from the group b10), in particular selected from isoxazoline compounds of Formulas 11.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9 as defined above.
  • a tenth preferred embodiment of the invention relates to compositions according to the invention which, in addition to a piperazinedione compound of the formula I, especially an active compound from the group 1-1 to 1-146, at least one and especially exactly one herbicidal active compound from the group b1 1), in particular Containing isoxaben.
  • An eleventh preferred embodiment of the invention relates to compositions according to the invention which, in addition to a piperazinedione compound of the formula I, especially an active compound from the group 1-1 to 1-146, at least one and especially exactly one herbicidal active substance from the group b13), in particular selected from 2 , 4-D and its salts and esters, aminopyralid and its salts such as aminopyralid tris (2-hydroxypropyl) ammonium and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, fluroxypyr-meptyl, quinclorac, quinmerac and 5,6-dichloro-2-cyclopropyl-4-pyrimidinecarboxylic acid (CAS 858956-08-8) and its salts and esters.
  • a piperazinedione compound of the formula I especially an active compound from the group 1-1 to 1-146, at least one and especially exactly one herbicidal active substance from the group b13
  • a twelfth preferred embodiment of the invention relates to compositions according to the invention which, in addition to a piperazinedione compound of the formula I, especially an active compound from the group 1-1 to 1-146, at least one and especially exactly one herbicidal active substance from group b14), in particular selected from Diflu - contain fenzopyr and diflufenzopyr sodium.
  • a 14th preferred embodiment of the invention relates to compositions according to the invention which, in addition to a piperazinedione compound of the formula I, especially an active compound from the group 1-1 to 1-146, at least one and especially exactly one nen herbicidal active ingredient from the safener C, in particular Benoxacor, Cloquintocet, Cyprosulfamide, Dichlormid, Fenchlorazole, Isoxadifen, Mefenpyr, 4- (Dichloroacetyl) -1-oxa-4-azaspiro [4.5] decane (MON4660, CAS 71526-07-3) and 2,2,5-trimethyl-3- (dichloroacetyl) -1,3-oxazolidine (R-29148, CAS 52836-31-4).
  • a piperazinedione compound of the formula I especially an active compound from the group 1-1 to 1-146, at least one and especially exactly one nen herbicidal active ingredient from the safener C, in particular Benoxa
  • compositions which correspond to the binary compositions of the 1st to 13th embodiments and additionally comprise a safener C, in particular selected from Benoxacor, Cocoquintocet, Cyprosulfamide, Dichlormid, Fenchlorazole, Isoxadifen, Mefenpyr, 4- (dichloroacetyl) 1-oxa-4-azaspiro [4.5] decane (MON4660, CAS 71526-07-3) and 2,2,5-trimethyl-3- (dichloroacetyl) -1,3-oxazolidine (R-29148, CAS 52836- 31-4).
  • a safener C in particular selected from Benoxacor, Cocoquintocet, Cyprosulfamide, Dichlormid, Fenchlorazole, Isoxadifen, Mefenpyr, 4- (dichloroacetyl) 1-oxa-4-azaspiro [4.5] decane (MON4660, CAS 71526-07-3) and 2,2,
  • binary compositions here and below includes those compositions which contain one or more, e.g. 1, 2 or 3 active compounds of the formula I and either one or more, e.g. 1, 2 or 3 herbicides B or one or more safeners. Accordingly, the term “ternary compositions” includes those compositions containing one or more, e.g. 1, 2 or 3 active compounds of the formula I, one or more, e.g. 1, 2 or 3 herbicides B and one or more, z. B. 1, 2 or 3 safeners C included.
  • the weight ratio of the active compounds A: B is generally in the range from 1: 1000 to 1000: 1, preferably in the range from 1: 500 to 500: 1, in particular in the range of 1: 250 to 250: 1 and particularly preferably in the range of 1: 75 to 75: 1.
  • the weight ratio of the active compounds A: C is generally in the range from 1: 1000 to 1000: 1, preferably in the range from 1: 500 to 500: 1, in particular in the range of 1: 250 to 250: 1 and particularly preferably in the range of 1: 75 to 75: 1.
  • the relative proportions by weight of the components A: B are generally in the range from 1: 1000 to 1000: 1, preferably in the range from 1: 500 to 500: 1, in particular in the range from 1: 250 to 250: 1 and more preferably in the range from 1: 75 to 75: 1,
  • the weight ratio of component A: C is generally in the Range of 1: 1000 to 1000: 1, preferably in the range of 1: 500 to 500: 1, in particular in the range of 1: 250 to 250: 1 and more preferably in the range of 1: 75 to 75: 1
  • the weight ratio of the components B: C generally in the range from 1: 1000 to 1000: 1, preferably in the range from 1: 500 to 500: 1, in particular in the range from 1: 250 to 250: 1 and particularly preferably in the range from 1: 75 to 75: 1.
  • the weight ratio of components A + B to component C is preferably in the range from 1: 500 to 500: 1, in particular in the range from 1: 250 to 250: 1 and particularly preferably in the range from 1: 75 to 75: 1. Examples of particularly preferred mixing partners and mixing partner combinations are given in the following Table A. Table A:
  • compositions containing as active ingredient A) the piperazine compound 1-1 and, as further active ingredient, the substance (s) indicated in a row of Table A Compositions 1.1 to 1.1227).
  • the weight ratios of the individual constituents in the compositions 1.1 to 1.1227 are within the limits specified above, in particular within the preferred limits.
  • Table 1a Compositions 1.1 a to 1.1227a, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as active ingredient A) the Z-isomer of the compound 1-1.
  • compositions 2.1 to 2.1227 which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-2.
  • Table 2a Compositions 2.1 a to 2.1227 a, which differ from the corresponding compositions 2.1 to 2.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-2.
  • Table 3 Compositions 3.1 to 3.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that as active ingredient A) they contain the compound I-3.
  • Table 3a Compositions 3.1 a to 3.1227a, which differ from the corresponding compositions 3.1 to 3.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-3.
  • compositions 4.1 to 4.1227 which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-4.
  • Table 4a Compositions 4.1a to 4.1227a, which differ from the corresponding compositions 4.1 to 4.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-4.
  • Table 5 Compositions 5.1 to 5.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-5.
  • Table 5a Compositions 5.1 a to 5.1227 a, which differ from the corresponding compositions 5.1 to 5.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-5.
  • compositions 6.1 to 6.1227 which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-6.
  • Table 6a Compositions 6.1a to 6.1227a, which differ from the corresponding compositions 6.1 to 6.1227 only in that they contain as active ingredient A) the Z-isomer of compound I-6.
  • Table 7 Compositions 7.1 to 7.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-7.
  • Table 7a Compositions 7.1a to 7.1227a, which differ from the corresponding compositions 7.1 to 7.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-7.
  • Table 8 Compositions 8.1 to 8.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-8.
  • Table 8a Compositions 8.1a to 8.1227a, which differ from the corresponding compositions 8.1 to 8.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-8.
  • compositions 9.1 to 9.1227 which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-9.
  • Table 9a Compositions 9.1 a to 9.1227a, which differ from the corresponding compositions 9.1 to 9.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-9.
  • Table 10 Compositions 10.1 to 10.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as active ingredient A) the compound 1-10.
  • Table 10a Compositions 10.1 a to 10.1227a, which differ from the corresponding compositions 10.1-10.1227 only in that they contain the Z-isomer of the compound 1-10.
  • compositions 11.1 to 1.1227 which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain the compound 1-1 1 as active ingredient A).
  • Table 1 1a Compositions 1.1.1a to 11.1227a, which differ from the corresponding compositions 11.1-11.1227 only in that as active ingredient A) they contain the Z isomer of compound 1-1.
  • Table 12 Compositions 12.1 to 12.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as active ingredient A) the compound 1-12.
  • Table 12a Compositions 12.1a to 12.1227a, which differ from the corresponding compositions 12.1 - 12.1227 only in that as active ingredient A) they contain the Z-isomer of the compound 1-12.
  • Table 13 Compositions 13.1 to 13.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as active ingredient A) the compound 1-13.
  • Table 13a Compositions 13.1 a to 13.1227a, which differ from the corresponding compositions 13.1-13.1227 only in that they contain as active ingredient A) the Z-isomer of the compound 1-13.
  • Table 14 Compositions 14.1 to 14.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as active ingredient A) the compound 1-14.
  • Table 14a Compositions 14.1 a to 14.1227a, which differ from the corresponding compositions 14.1-14.1227 only in that as active ingredient A) they contain the Z-isomer of the compound 1-14.
  • Table 15 Compositions 15.1 to 15.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as active ingredient A) the compound 1-15.
  • Table 15a Compositions 15.1 a to 15.1227a, which differ from the corresponding compositions 15.1-15.1227 only in that they contain as active ingredient A) the Z-isomer of the compound 1-15.
  • Table 16 Compositions 16.1 to 16.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain the compound 1-16 as active ingredient A).
  • Table 16a Compositions 16.1a to 16.1227a, which differ from the corresponding compositions 16.1-16.1227 only in that as active ingredient A) they contain the Z-isomer of the compound 1-16.
  • Table 17 Compositions 17.1 to 17.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as active ingredient A) the compound 1-17.
  • Table 17a Compositions 17.1 a to 17.1227a, which differ from the corresponding compositions 17.1-17.1227 only in that they contain as active ingredient A) the Z-isomer of the compound 1-17.
  • compositions 18.1 to 18.1227 which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as active ingredient A) the compound 1-18.
  • Table 18a Compositions 18.1 a to 18.1227a, which differ from the corresponding compositions 18.1-18.1227 only in that they contain as active ingredient A) the Z-isomer of the compound 1-18.
  • Table 19 Compositions 19.1 to 19.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as active ingredient A) the compound 1-19.
  • Table 19a Compositions 19.1 a to 19.1227a, which differ from the corresponding compositions 19.1-19.1227 only in that they contain as active ingredient A) the Z-isomer of the compound 1-19.
  • compositions 20.1 to 20.1227 which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-20.
  • compositions 20.1a to 20.1227a which differ from the corresponding compositions 20.1-20.1227 only in that as active ingredient A) they contain the Z-isomer of the compound I-20.
  • Table 21 Compositions 21.1 to 21.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound 1-21.
  • Table 21a Compositions 21.1 a to 21.1227a, which differ from the corresponding compositions 21.1 - 21.1227 only in that they contain as active ingredient A) the Z-isomer of the compound 1-21.
  • compositions 22.1 to 22.1227 which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-22.
  • Table 22a Compositions 22.1 a to 22.1227a, which differ from the corresponding compositions 22.1 - 22.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-22.
  • Table 23 Compositions 23.1 to 23.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain the compound I-23 as active ingredient A).
  • Table 23a Compositions 23.1a to 23.1227a, which differ from the corresponding compositions 23.1 - 23.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-23.
  • Table 24 Compositions 24.1 to 24.1227, which differ from the corresponding compositions 1.1 to 1.1227 merely in that they contain as compound A) the compound I-24.
  • Table 24a Compositions 24.1 a to 24.1227a, which differ from the corresponding compositions 24.1 - 24.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-24.
  • compositions 25.1 to 25.1227 which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-25.
  • Table 25a Compositions 25.1 a to 25.1227a, which differ from the corresponding compositions 25.1 - 25.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-25.
  • Table 26 Compositions 26.1 to 26.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-26.
  • Table 26a Compositions 26.1 a to 26.1227a, which differ from the corresponding compositions 26.1 - 26.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-26.
  • compositions 27.1 to 27.1227 which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-27.
  • Table 27a Compositions 27.1 a to 27.1227a, which differ from the corresponding compositions 27.1 - 27.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-27.
  • Table 28 Compositions 28.1 to 28.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-28.
  • Table 28a Compositions 28.1 a to 28.1227a, which differ from the corresponding compositions 28.1 - 28.1227 only in that they contain the Z-isomer of the compound I-28.
  • compositions 29.1 to 29.1227 which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-29.
  • Table 29a Compositions 29.1 a to 29.1227a, which differ from the corresponding compositions 29.1 - 29.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-29.
  • compositions 30.1 to 30.1227 which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-30.
  • Table 30a Compositions 30.1 a to 30.1227a, which differ from the corresponding compositions 30.1-30.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-30.
  • Table 31 Compositions 31.1 to 31.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound 1-31.
  • Table 31 a Compositions 31.1 a to 31.1227a, which differ from the corresponding compositions 31.1 - 31.1227 only in that they contain as active ingredient A) the Z-isomer of the compound 1-31.
  • Table 32 Compositions 32.1 to 32.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain the compound I-32 as active ingredient A).
  • Table 32a Compositions 32.1 a to 32.1227a, which differ from the corresponding compositions 32.1 - 32.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-32.
  • Table 33 Compositions 33.1 to 33.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-33.
  • Table 33a Compositions 33.1a to 33.1227a, which differ from the corresponding compositions 33.1-33.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-33.
  • compositions 34.1 to 34.1227 which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-34.
  • compositions 34.1 a to 34.1227a which differ from the corresponding compositions 34.1-34.1227 only in that they contain as active ingredient A) the Z-isomer of compound I-34.
  • Table 35 Compositions 35.1 to 35.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-35.
  • Table 35a Compositions 35.1a to 35.1227a, which differ from the corresponding compositions 35.1 - 35.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-35.
  • Table 36 Compositions 36.1 to 36.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-36.
  • Table 36a Compositions 36.1a to 36.1227a, which differ from the corresponding compositions 36.1-36.1227 only in that they contain as active ingredient A) the Z-isomer of compound I-36.
  • Table 37 Compositions 37.1 to 37.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain the compound I-37 as active ingredient A).
  • Table 37a Compositions 37.1a to 37.1227a, which differ from the corresponding compositions 37.1 - 37.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-37.
  • Table 38 Compositions 38.1 to 38.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-38.
  • Table 38a Compositions 38.1a to 38.1227a, which differ from the corresponding compositions 38.1-38.1227 only in that they contain as active ingredient A) the Z-isomer of compound I-38.
  • compositions 39.1 to 39.1227 which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain the compound I-39 as active ingredient A).
  • Table 39a Compositions 39.1a to 39.1227a, which differ from the corresponding compositions 39.1 - 39.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-39.
  • Table 40 Compositions 40.1 to 40.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-40.
  • Table 40a Compositions 40.1a to 40.1227a, which differ from the corresponding compositions 40.1 - 40.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-40.
  • compositions 41.1 to 41.1227 which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound 1-41.
  • Table 41a Compositions 41.1a to 41.1227a, which differ from the corresponding compositions 41.1-41.1227 merely in that they contain as active ingredient A) the Z-isomer of compound 1-41.
  • Table 42 Compositions 42.1 to 42.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-42.
  • Table 42a Compositions 42.1a to 42.1227a, which differ from the corresponding compositions 42.1 - 42.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-42.
  • Table 43 Compositions 43.1 to 43.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-43.
  • Table 43a Compositions 43.1a to 43.1227a, which differ from the corresponding compositions 43.1-43.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-43.
  • compositions 44.1 to 44.1227 which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-44.
  • Table 44a Compositions 44.1a to 44.1227a, which differ from the corresponding compositions 44.1-44.1227 only in that they contain as active ingredient A) the Z-isomer of compound I-44.
  • Table 45 Compositions 45.1 to 45.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-45.
  • Table 45a Compositions 45.1a to 45.1227a, which differ from the corresponding compositions 45.1-45.1227 only in that they contain the Z-isomer of compound I-45.
  • compositions 46.1 to 46.1227 which differ from the corresponding compositions 1.1 to 1.1227 merely in that they contain compound I-46 as active ingredient A).
  • Table 46a Compositions 46.1a to 46.1227a, which differ from the corresponding compositions 46.1-46.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-46.
  • Table 47 Compositions 47.1 to 47.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-47.
  • Table 47a Compositions 47.1a to 47.1227a, which differ from the corresponding compositions 47.1-47.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-47.
  • Table 48 Compositions 48.1 to 48.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-48.
  • Table 48a Compositions 48.1a to 48.1227a, which differ from the corresponding compositions 48.1-48.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-48.
  • Table 49 Compositions 49.1 to 49.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-49.
  • Table 49a Compositions 49.1a to 49.1227a, which differ from the corresponding compositions 49.1-49.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-49.
  • compositions 50.1 to 50.1227 which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-50.
  • compositions 50.1a to 50.1227a which differ from the corresponding compositions 50.1 - 50.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-50.
  • Table 51 Compositions 51.1 to 51.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain the compound 1-51 as active ingredient A).
  • Table 51a Compositions 51.1a to 51.1227a, which differ from the corresponding compositions 51.1 - 51.1227 only in that they contain as active ingredient A) the Z-isomer of the compound 1-51.
  • Table 52 Compositions 52.1 to 52.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-52.
  • Table 52a Compositions 52.1a to 52.1227a, which differ from the corresponding compositions 52.1 - 52.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-52.
  • Table 53 Compositions 53.1 to 53.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain the compound I-53.
  • Table 53a Compositions 53.1a to 53.1227a, which differ from the corresponding compositions 53.1-53.1227 only in that they contain the Z-isomer of compound I-53.
  • Table 54 Compositions 54.1 to 54.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-54.
  • Table 54a Compositions 54.1a to 54.1227a, which differ from the corresponding compositions 54.1-54.1227 only in that they contain as active ingredient A) the Z-isomer of compound I-54.
  • compositions 55.1 to 55.1227 which differ from the corresponding compositions 1.1 to 1.1227 merely in that they contain as compound A) the compound I-55.
  • Table 55a Compositions 55.1a to 55.1227a, which differ from the corresponding compositions 55.1-55.1227 only in that they contain the Z-isomer of compound I-55.
  • Table 56 Compositions 56.1 to 56.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-56.
  • Table 56a Compositions 56.1a to 56.1227a, which differ from the corresponding compositions 56.1-56.1227 only in that they contain as active ingredient A) the Z-isomer of compound I-56.
  • Table 57 Compositions 57.1 to 57.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-57.
  • Table 57a Compositions 57.1a to 57.1227a, which differ from the corresponding compositions 57.1 - 57.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-57.
  • Table 58 Compositions 58.1 to 58.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain the compound I-58 as active ingredient A).
  • Table 58a Compositions 58.1a to 58.1227a, which differ from the corresponding compositions 58.1-58.1227 only in that they contain as active ingredient A) the Z-isomer of compound I-58.
  • Table 59 Compositions 59.1 to 59.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-59.
  • Table 59a Compositions 59.1a to 59.1227a, which differ from the corresponding compositions 59.1-59.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-59.
  • Table 60 Compositions 60.1 to 60.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain the compound I-60 as active ingredient A).
  • Table 60a Compositions 60.1a to 60.1227a, which differ from the corresponding compositions 60.1-60.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-60.
  • Table 61 Compositions 61.1 to 61.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain the compound 1-61 as active ingredient A).
  • Table 61a Compositions 61.1a to 61.1227a, which differ from the corresponding compositions 61.1 - 61.1227 only in that they contain as active ingredient A) the Z-isomer of the compound 1-61.
  • Table 62 Compositions 62.1 to 62.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-62.
  • Table 62a Compositions 62.1a to 62.1227a, which differ from the corresponding compositions 62.1-62.1227 only in that they contain as active ingredient A) the Z-isomer of compound I-62.
  • Table 63 Compositions 63.1 to 63.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain the compound I-63 as active ingredient A).
  • Table 63a Compositions 63.1a to 63.1227a, which differ from the corresponding compositions 63.1-63.1227 only in that they contain as active ingredient A) the Z-isomer of compound I-63.
  • Table 64 Compositions 64.1 to 64.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-64.
  • Table 64a Compositions 64.1 a to 64.1227a, which differ from the corresponding compositions 64.1-64.1227 only in that they contain as active ingredient A) the Z-isomer of compound I-64.
  • Table 65 Compositions 65.1 to 65.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-65.
  • Table 65a Compositions 65.1a to 65.1227a, which differ from the corresponding compositions 65.1-65.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-65.
  • Table 66 Compositions 66.1 to 66.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-66.
  • Table 66a Compositions 66.1a to 66.1227a, which differ from the corresponding compositions 66.1 - 66.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-66.
  • Table 67 Compositions 67.1 to 67.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain the compound I-67 as active ingredient A).
  • Table 67a Compositions 67.1a to 67.1227a, which differ from the corresponding compositions 67.1-67.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-67.
  • Table 68 Compositions 68.1 to 68.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-68.
  • Table 68a Compositions 68.1a to 68.1227a, which differ from the corresponding compositions 68.1-68.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-68.
  • Table 69 Compositions 69.1 to 69.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-69.
  • Table 69a Compositions 69.1a to 69.1227a, which differ from the corresponding compositions 69.1-69.1227 only in that they contain as active ingredient A) the Z-isomer of compound I-69.
  • Table 70 Compositions 70.1 to 70.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-70.
  • Table 70a Compositions 70.1a to 70.1227a, which differ from the corresponding compositions 70.1-70.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-70.
  • Table 71 Compositions 71.1 to 71.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain the compound 1-71 as active ingredient A).
  • Table 71a Compositions 71.1a to 71.1227a, which differ from the corresponding compositions 71.1-71.1227 only in that they contain as active ingredient A) the Z-isomer of the compound 1-71.
  • Table 72 Compositions 72.1 to 72.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain the compound I-72 as active ingredient A).
  • Table 72a Compositions 72.1a to 72.1227a, which differ from the corresponding compositions 72.1 - 72.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-72.
  • Table 73 Compositions 73.1 to 73.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-73.
  • Table 73a Compositions 73.1a to 73.1227a, which differ from the corresponding compositions 73.1 - 73.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-73.
  • Table 74 Compositions 74.1 to 74.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain the compound I-74 as active ingredient A).
  • Table 74a Compositions 74.1a to 74.1227a, which differ from the corresponding compositions 74.1-74.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-74.
  • Table 75 Compositions 75.1 to 75.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-75.
  • Table 75a Compositions 75.1 a to 75.1227a, which differ from the corresponding compositions 75.1-75.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-75.
  • Table 76 Compositions 76.1 to 76.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-76.
  • Table 76a Compositions 76.1a to 76.1227a, which differ from the corresponding compositions 76.1-76.1227 only in that they contain as active ingredient A) the Z-isomer of compound I-76.
  • Table 77 Compositions 77.1 to 77.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-77.
  • Table 77a Compositions 77.1a to 77.1227a, which differ from the corresponding compositions 77.1-77.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-77.
  • Table 78 Compositions 78.1 to 78.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-78.
  • Table 78a Compositions 78.1a to 78.1227a, which differ from the corresponding compositions 78.1-78.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-78.
  • Table 79 Compositions 79.1 to 79.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-79.
  • Table 79a Compositions 79.1a to 79.1227a, which differ from the corresponding compositions 79.1-79.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-79.
  • Table 80 Compositions 80.1 to 80.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-80.
  • Table 80a Compositions 80.1a to 80.1227a, which differ from the corresponding compositions 80.1-80.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-80.
  • Table 81 Compositions 81.1 to 81.1227, which differ from the corresponding compositions 1.1 to 1.1227 merely in that they contain compound 1-81 as active ingredient A).
  • Table 81a Compositions 81.1a to 81.1227a, which differ from the corresponding compositions 81.1 - 81.1227 only in that they contain as active ingredient A) the Z-isomer of the compound 1-81.
  • Table 82 Compositions 82.1 to 82.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-82.
  • Table 82a Compositions 82.1a to 82.1227a, which differ from the corresponding compositions 82.1 - 82.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-82.
  • Table 83 Compositions 83.1 to 83.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-83.
  • Table 83a Compositions 83.1a to 83.1227a, which differ from the corresponding compositions 83.1-83.1227 only in that they contain as active ingredient A) the Z-isomer of compound I-83.
  • Table 84 Compositions 84.1 to 84.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-84.
  • Table 84a Compositions 84.1a to 84.1227a, which differ from the corresponding compositions 84.1-84.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-84.
  • Table 85 Compositions 85.1 to 85.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain the compound I-85.
  • compositions 85.1a to 85.1227a which differ from the corresponding compositions 85.1-85.1227 only in that they contain as active ingredient A) the Z-isomer of compound I-85.
  • Table 86 Compositions 86.1 to 86.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain the compound I-86 as active ingredient A).
  • Table 86a Compositions 86.1 a to 86.1227a, which differ from the corresponding compositions 86.1-86.1227 only in that they contain as active ingredient A) the Z-isomer of compound I-86.
  • Table 87 Compositions 87.1 to 87.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-87.
  • Table 87a Compositions 87.1a to 87.1227a, which differ from the corresponding compositions 87.1-87.1227 only in that they contain as active ingredient A) the Z-isomer of compound I-87.
  • Table 88 Compositions 88.1 to 88.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-88.
  • Table 88a Compositions 88.1a to 88.1227a, which differ from the corresponding compositions 88.1 - 88.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-88.
  • Table 89 Compositions 89.1 to 89.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-89.
  • Table 89a Compositions 89.1a to 89.1227a, which differ from the corresponding compositions 89.1 - 89.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-89.
  • compositions 90.1 to 90.1227 which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-90.
  • Table 90a Compositions 90.1a to 90.1227a, which differ from the corresponding compositions 90.1-90.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-90.
  • Table 91 Compositions 91.1 to 91.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain the compound 1-91 as active ingredient A).
  • Table 91a Compositions 91.1a to 91.1227a, which differ from the corresponding compositions 91.1 - 91.1227 only in that they contain as active ingredient A) the Z-isomer of the compound 1-91.
  • Table 92 Compositions 92.1 to 92.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-92.
  • Table 92a Compositions 92.1a to 92.1227a, which differ from the corresponding compositions 92.1 - 92.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-92.
  • Table 93 Compositions 93.1 to 93.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain the compound I-93 as active ingredient A).
  • Table 93a Compositions 93.1a to 93.1227a, which differ from the corresponding compositions 93.1 - 93.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-93.
  • Table 94 Compositions 94.1 to 94.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-94.
  • Table 94a Compositions 94.1a to 94.1227a, which differ from the corresponding compositions 94.1 - 94.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-94.
  • Table 95 Compositions 95.1 to 95.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain the compound I-95 as active ingredient A).
  • Table 95a Compositions 95.1a to 95.1227a, which differ from the corresponding compositions 95.1-95.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-95.
  • Table 96 Compositions 96.1 to 96.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain the compound I-96 as active ingredient A).
  • Table 96a Compositions 96.1a to 96.1227a, which differ from the corresponding compositions 96.1-96.1227 only in that they contain as active ingredient A) the Z-isomer of compound I-96.
  • Table 97 Compositions 97.1 to 97.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-97.
  • Table 97a Compositions 97.1a to 97.1227a, which differ from the corresponding compositions 97.1 - 97.1227 only in that they contain as active ingredient A) the Z-isomer of compound I-97.
  • Table 98 Compositions 98.1 to 98.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-98.
  • Table 98a Compositions 98.1a to 98.1227a, which differ from the corresponding compositions 98.1-98.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-98.
  • compositions 99.1 to 99.1227 which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound I-99.
  • compositions 99.1a to 99.1227a which differ from the corresponding compositions 99.1-99.1227 only in that they contain as active ingredient A) the Z-isomer of the compound I-99.
  • Table 100 Compositions 100.1 to 100.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain the compound 1-100 as active ingredient A).
  • Table 100a Compositions 100.1a to 100.1227a, which differ from the corresponding compositions 100.1 - 100.1227 only in that they contain as active ingredient A) the Z-isomer of the compound 1-100.
  • Table 101 Compositions 101.1 to 101.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as active ingredient A) the compound 1-101.
  • Table 101a Compositions 101.1 a to 101.1227a, which differ from the corresponding compositions 101.1 - 101.1227 only in that they contain as active ingredient A) the Z-isomer of the compound 1-101.
  • Table 102 Compositions 102.1 to 102.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain compound 1-102 as active ingredient A).
  • Table 102a Compositions 102.1 a to 102.1227a, which differ from the corresponding compositions 102.1 - 102.1227 only in that they contain as active ingredient A) the Z-isomer of the compound 1-102.
  • Table 103 Compositions 103.1 to 103.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as active ingredient A) the compound 1-103.
  • Table 103a Compositions 103.1 a to 103.1227a, which differ from the corresponding compositions 103.1-103.1227 merely in that they contain as active ingredient A) the cis isomer of compound 1-103.
  • Table 104 Compositions 104.1 to 104.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as active ingredient A) the compound 1-104.
  • Table 104a Compositions 104.1 a to 104.1227a, which differ from the corresponding compositions 104.1-104.1227 only in that they contain as active ingredient A) the cis isomer of compound 1-104.
  • Table 105 Compositions 105.1 to 105.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as active ingredient A) the compound 1-105.
  • Table 105a Compositions 105.1 a to 105.1227a, which differ from the corresponding compositions 105.1-105.1227 only in that they contain as active ingredient A) the cis isomer of compound 1-105.
  • Table 106 Compositions 106.1 to 106.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as active ingredient A) the compound 1-106.
  • Table 106a Compositions 106.1 a to 106.1227a, which differ from the corresponding compositions 106.1-106.1227 only in that they contain as active ingredient A) the cis isomer of compound 1-106.
  • Table 107 Compositions 107.1 to 107.1227, which differ from the corresponding compositions 1.1 to 1.1227 merely in that they contain compound 1-107 as active ingredient A).
  • Table 107a Compositions 107.1 a to 107.1227a, which differ from the corresponding compositions 107.1 - 107.1227 only in that they contain as active ingredient A) the cis isomer of the compound 1-107.
  • Table 108 Compositions 108.1 to 108.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as active ingredient A) the compound 1-108.
  • Table 108a Compositions 108.1 a to 108.1227a, which differ from the corresponding compositions 108.1 - 108.1227 only in that they contain as active ingredient A) the cis isomer of compound 1-108.
  • Table 109 Compositions 109.1 to 109.1227, which differ from the corresponding compositions 1.1 to 1.1227 merely in that they contain compound 1-109 as active ingredient A).
  • Table 109a Compositions 109.1 a to 109.1227a, which differ from the corresponding compositions 109.1 - 109.1227 only in that they contain as active ingredient A) the cis isomer of the compound 1-109.
  • Table 1 10 Compositions 1 10.1 to 110.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as active ingredient A) the compound 1-110.
  • Table 110a Compositions 1 10.1 a to 1 10.1227a, which differ from the corresponding compositions 1 10.1 - 110.1227 only in that they contain as active ingredient A) the cis isomer of the compound 1-110.
  • Table 1 11 Compositions 11.1 to 11 1.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain the compound 1-11 1 as active ingredient A).
  • Table 11 1a Compositions 11.1a to 11.1227a, which differ from the corresponding compositions 1111-11.11227 only in that they contain as active ingredient A) the cis isomer of compound 1-11.
  • Table 1 12 Compositions 1 12.1 to 112.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound 1-112.
  • Table 112a Compositions 1 12.1 a to 1 12.1227a, which differ from the corresponding compositions 1 12.1 - 112.1227 only in that they contain as active ingredient A) the cis isomer of the compound 1-112.
  • Table 113 Compositions 1 13.1 to 113.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as active ingredient A) the compound 1-113.
  • Table 113a Compositions 1 13.1 a to 1 13.1227a, which differ from the corresponding compositions 1 13.1-113.1227 only in that they contain as active ingredient A) the cis isomer of compound 1-113.
  • Table 1 14 Compositions 1 14.1 to 114.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain the compound 1-114 as active ingredient A).
  • Table 114a Compositions 1 14.1 a to 1 14.1227a, which differ from the corresponding compositions 1 14.1 - 114.1227 only in that they contain as active ingredient A) the cis isomer of the compound 1-114.
  • Table 1 15 Compositions 1 15.1 to 115.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as active ingredient A) the compound 1-115.
  • Table 115a Compositions 1 15.1 a to 1 15.1227a, which differ from the corresponding compositions 1 15.1 - 115.1227 only in that they contain as active ingredient A) the cis isomer of the compound 1-115.
  • Table 1 16 Compositions 1 16.1 to 116.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain compound 1-116 as active ingredient A).
  • Table 116a Compositions 116.1a to 116.1227a, which differ from the corresponding compositions 1 16.1-116.1227 only in that they contain as active ingredient A) the cis isomer of compound 1-116.
  • Table 1 17 Compositions 1 17.1 to 117.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as active ingredient A) the compound 1-117.
  • Table 117a Compositions 1 17.1 a to 1 17.1227a, which differ from the corresponding compositions 1 17.1 - 117.1227 only in that they contain as active ingredient A) the cis isomer of the compound 1-117.
  • Table 1 18 Compositions 1 18.1 to 118.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as active ingredient A) the compound 1-118.
  • Table 118a Compositions 1 18.1 a to 1 18.1227a, which differ from the corresponding compositions 1 18.1-118.1227 only in that they contain as active ingredient A) the cis isomer of compound 1-118.
  • Table 1 19 Compositions 1 19.1 to 119.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as active ingredient A) the compound 1-119.
  • Table 119a Compositions 1 19.1 a to 1 19.1227a, which differ from the corresponding compositions 1 19.1 - 119.1227 only in that they contain as active ingredient A) the cis isomer of the compound 1-119.
  • Table 120 Compositions 120.1 to 120.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as active ingredient A) the compound 1-120.
  • Table 120a Compositions 120.1 a to 120.1227a, which differ from the corresponding compositions 120.1-120.1227 only in that they contain as active ingredient A) the cis isomer of compound 1-120.
  • Table 121 Compositions 121.1 to 121.1227, which differ from the corresponding compositions 1.1 to 1.1227 merely in that they contain compound 1-121 as active ingredient A).
  • Table 121a Compositions 121.1 a to 121.1227a, which differ from the corresponding compositions 121.1-121.1227 merely in that they contain as active ingredient A) the cis isomer of compound 1-121.
  • Table 122 Compositions 122.1 to 122.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain compound 1-122 as active ingredient A).
  • Table 122a Compositions 122.1 a to 122.1227a, which differ from the corresponding compositions 122.1 - 122.1227 only in that they contain as active ingredient A) the cis isomer of compound 1-122.
  • Table 123 Compositions 123.1 to 123.1227, which differ from the corresponding compositions 1.1 to 1.1227 merely in that they contain compound 1-123 as active ingredient A).
  • Table 123a Compositions 123.1 a to 123.1227a, which differ from the corresponding compositions 123.1 - 123.1227 merely in that they contain as active ingredient A) the cis isomer of compound 1-123.
  • Table 124 Compositions 124.1 to 124.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as active ingredient A) the compound 1-124.
  • Table 124a Compositions 124.1 a to 124.1227a, which differ from the corresponding compositions 124.1-124.1227 only in that they contain as active ingredient A) the cis isomer of compound 1-124.
  • Table 125 Compositions 125.1 to 125.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as active ingredient A) the compound 1-125.
  • Table 125a Compositions 125.1 a to 125.1227a, which differ from the corresponding compositions 125.1 - 125.1227 only in that they contain as active ingredient A) the cis isomer of compound 1-125.
  • Table 126 Compositions 126.1 to 126.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as active ingredient A) the compound 1-126.
  • Table 126a Compositions 126.1a to 126.1227a, which differ from the corresponding compositions 126.1-126.1227 only in that they contain as active ingredient A) the cis isomer of compound 1-126.
  • Table 127 Compositions 127.1 to 127.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as active ingredient A) the compound 1-127.
  • Table 127a Compositions 127.1 a to 127.1227a, which differ from the corresponding compositions 127.1 - 127.1227 only in that they contain as active ingredient A) the cis isomer of the compound 1-127.
  • compositions 128.1 to 128.1227 which differ from the corresponding compositions 1.1 to 1.1227 merely in that they contain compound 1-128 as active ingredient A).
  • Table 128a Compositions 128.1 a to 128.1227a, which differ from the corresponding compositions 128.1 - 128.1227 only in that they contain as active ingredient A) the cis isomer of the compound 1-128.
  • Table 129 Compositions 129.1 to 129.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as active ingredient A) the compound 1-129.
  • Table 129a Compositions 129.1 a to 129.1227a, which differ from the corresponding compositions 129.1 - 129.1227 only in that they contain as active ingredient A) the cis isomer of the compound 1-129.
  • Table 130 Compositions 130.1 to 130.1227, which differ from the corresponding compositions 1.1 to 1.1227 merely in that they contain the compound 1-130 as active ingredient A).
  • Table 130a Compositions 130.1 a to 130.1227a, which differ from the corresponding compositions 130.1-130.1227 only in that, as active ingredient A), they contain the cis isomer of compound 1-130.
  • Table 131 Compositions 131.1 to 131.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound 1-131.
  • Table 131a Compositions 131.1 a to 131.1227a, which differ from the corresponding compositions 131.1-131.1227 merely in that they contain as active ingredient A) the cis isomer of compound 1-131.
  • Table 132 Compositions 132.1 to 132.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound 1-132.
  • Table 132a Compositions 132.1a to 132.1227a, which differ from the corresponding compositions 132.1 - 132.1227 only in that they contain as active ingredient A) the cis isomer of compound 1-132.
  • Table 133 Compositions 133.1 to 133.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound 1-133.
  • Table 133a Compositions 133.1 a to 133.1227a, which differ from the corresponding compositions 133.1 - 133.1227 only in that they contain as active ingredient A) the cis isomer of compound 1-133.
  • Table 134 Compositions 134.1 to 134.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain the compound 1-134 as active ingredient A).
  • Table 134a Compositions 134.1 a to 134.1227a, which differ from the corresponding compositions 134.1-134.1227 only in that they contain as active ingredient A) the cis isomer of compound 1-134.
  • Table 135 Compositions 135.1 to 135.1227, which differ from the corresponding compositions 1.1 to 1.1227 merely in that they contain compound 1-135 as active ingredient A).
  • Table 135a Compositions 135.1 a to 135.1227a, which differ from the corresponding compositions 135.1 - 135.1227 only in that they contain as active ingredient A) the cis isomer of compound 1-135.
  • Table 136 Compositions 136.1 to 136.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain the compound 1-136 as active ingredient A).
  • Table 136a Compositions 136.1 a to 136.1227a, which differ from the corresponding compositions 136.1-136.1227 only in that they contain as active ingredient A) the cis isomer of compound 1-136.
  • Table 137 Compositions 137.1 to 137.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain the compound 1-137 as active ingredient A).
  • Table 137a Compositions 137.1 a to 137.1227a, which differ from the corresponding compositions 137.1-137.1227 only in that they contain as active ingredient A) the cis isomer of compound 1-137.
  • Table 138 Compositions 138.1 to 138.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as active ingredient A) the compound 1-138.
  • Table 138a Compositions 138.1 a to 138.1227a, which differ from the corresponding compositions 138.1 - 138.1227 only in that they contain as active ingredient A) the cis isomer of the compound 1-138.
  • Table 139 Compositions 139.1 to 139.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as active ingredient A) the compound 1-139.
  • Table 139a Compositions 139.1 a to 139.1227a, which differ from the corresponding compositions 139.1-139.1227 only in that they contain as active ingredient A) the cis isomer of compound 1-139.
  • Table 140 Compositions 140.1 to 140.1227, which differ from the corresponding compositions 1.1 to 1.1227 merely in that they contain as compound A) the compound 1-140.
  • Table 140a Compositions 140.1a to 140.1227a, which differ from the corresponding compositions 140.1 - 140.1227 only in that they contain as active ingredient A) the cis isomer of the compound 1-140.
  • Table 141 Compositions 141.1 to 141.1227, which differ from the corresponding compositions 1.1 to 1.1227 merely in that they contain as compound A) the compound 1-141.
  • Table 141a Compositions 141.1 a to 141.1227a, which differ from the corresponding compositions 141.1 - 141.1227 only in that they contain as active ingredient A) the cis isomer of the compound 1-141.
  • Table 142 Compositions 142.1 to 142.1227, which differ from the corresponding compositions 1.1 to 1.1227 merely in that they contain compound 1-142 as active ingredient A).
  • Table 142a Compositions 142.1 a to 142.1227a, which differ from the corresponding compositions 142.1 - 142.1227 only in that they contain as active ingredient A) the cis isomer of the compound 1-142.
  • Table 143 Compositions 143.1 to 143.1227, which differ from the corresponding compositions 1.1 to 1.1227 only in that they contain as compound A) the compound 1-143.
  • Table 143a Compositions 143.1 a to 143.1227a, which differ from the corresponding compositions 143.1 - 143.1227 only in that they contain as active ingredient A) the cis isomer of the compound 1-143.
  • Table 144 Compositions 144.1 to 144.1227, which differ from the corresponding compositions 1.1 to 1.1227 merely in that they contain compound 1-144 as active ingredient A).
  • Table 144a Compositions 144.1 a to 144.1227a, which differ from the corresponding compositions 144.1 - 144.1227 only in that they contain as active ingredient A) the cis isomer of compound 1-144.
  • Table 145 Compositions 145.1 to 145.1227, which differ from the corresponding compositions 1.1 to 1.1227 merely in that they contain as compound A) the compound 1-145.
  • Table 145a Compositions 145.1a to 145.1227a, which differ from the corresponding compositions 145.1-145.1227 only in that they contain as active ingredient A) the cis isomer of compound 1-145.
  • Table 146 Compositions 146.1 to 146.1227, which differ from the corresponding compositions 1.1 to 1.1227 merely in that they contain compound 1-146 as active ingredient A).
  • Table 146a Compositions 146.1a to 146.1227a, which differ from the corresponding compositions 146.1-146.1227 only in that they contain as active ingredient A) the cis isomer of compound 1-146.
  • compositions of the invention are useful as herbicides. They are suitable as such or as appropriately formulated agent.
  • the compositions according to the invention combat plant growth on nonculture surfaces very well, especially at high application rates. In crops such as wheat, rice, corn, soybeans and cotton, they act against weeds and grass weeds without significantly damaging the crops. This effect occurs especially at low application rates.
  • compositions according to the invention can be used in a further number of crop plants to eliminate unwanted plants.
  • the following cultures may be considered:
  • the following cultures are contemplated: Arachis hypogaea, Beta vulgaris spec. altissima, Brassica napus var. napus, Brassica oleracea, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cynodon dactylon, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbalum, Gossypium vitifolium), Helianthus annuus, Hordeum vulgare, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Medica go sativa, Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Pistacia vera
  • compositions according to the invention can also be used in crops which are tolerant to the action of herbicides by breeding, including genetic engineering methods.
  • compositions of the invention may also be used in cultures tolerant by breeding, including genetic engineering against insects or fungal infestation.
  • compositions according to the invention are also suitable for the defoliation and / or desiccation of parts of plants, for which crop plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton, come into consideration.
  • crop plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton
  • compositions for the desiccation and / or defoliation of plants, processes for the preparation of these compositions and processes for the desiccation and / or defoliation of plants with the compositions according to the invention were found.
  • compositions of the invention are particularly suitable for dehydration of the aerial parts of crop plants such as potato, oilseed rape, sunflower and soybean but also cereals. This allows a completely mechanical harvesting of these important crops. Of economic interest is also the harvest relief, which is made possible by the time-concentrated dropping or reducing the adhesion to the tree in citrus fruits, olives or other types and varieties of pome, stone and peel fruit.
  • the same mechanism that is, the promotion of the formation of release tissue between fruit or leaf and shoot part of the plants is also essential for a well controllable defoliation of crops, especially cotton.
  • shortening the time interval in which the individual cotton plants ripen results in increased fiber quality after harvest.
  • compositions according to the invention or the plant protection agents containing them or formulated therefrom can be used, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, even high-percentage aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents or Granules can be applied by spraying, misting, dusting, scattering, pouring or treatment of the seed or mixing with the seed.
  • the forms of application depend on the intended use; In any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • the crop protection agents contain a herbicidally effective amount of the composition according to the invention, ie at least one compound I or an agriculturally useful salt of I and at least one other active ingredient, selected from herbicides B and the aforementioned safeners C, as well as for the formulation of pesticides customary excipients.
  • pesticides conventional auxiliaries are inert auxiliaries, solid or liquid carriers, surface-active substances (such as dispersants protective colloids, emulsifiers, wetting agents and adhesives), organic and inorganic thickeners, bactericides, antifreeze, defoamers, if necessary dyes and adhesives for seed formulations.
  • thickeners ie, compounds which impart modified flowability to the formulation, ie, high-level at low viscosity and low viscosity in the agitated state
  • thickeners are polysaccharides such as xanthan gum (Kelzan® from Kelco), Rhodopol® 23 (Rhone Poulenc) or Veegum ® (RT Vanderbilt) and organic and inorganic layer minerals such as Attaclay® (Engelhardt).
  • antifoaming agents are silicone emulsions (such as, for example, Silikon® SRE,
  • Bactericides may be added to stabilize the aqueous herbicidal formulation.
  • bactericides are bactericides based on diclorophene and benzyl alcohol hemiformal (Proxel® from the company ICI or Acticide® RS from Thor Chemie and Kathon® MK from Rohm & Haas) as well as isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones (Acticide MBS of Fa. Thor chemistry)
  • antifreeze agents are ethylene glycol, propylene glycol, urea or glycerol.
  • colorants are both water-insoluble pigments and water-soluble dyes. Examples which may be mentioned under the names rhodamine B, Cl. Pigment Red 1 12 and Cl.
  • Solvent Red 1 known dyes, as well as pigment blue 15: 4, pigment blue 15: 3, pigment blue 15: 2, pigment blue 15: 1, pigment blue 80, pigment yellow 1, pigment yellow 13, pigment red 1 12, pigment red 48: 2, pigment red 48: 1, pigment red 57: 1, pigment red 53: 1, pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51, acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.
  • adhesives examples include polyvinyl pyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose.
  • inert additives are in particular liquid or solid carrier in
  • liquid carrier examples include: medium to high boiling point mineral oil fractions such as kerosene or diesel oil, coal tar oils as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alkylated benzenes or their derivatives, alcohols such as methanol, ethanol, propanol, butanol, cyclohexanol, ketones such as cyclohexanone or strongly polar solvents, eg. As amines such as N-methylpyrrolidone or water.
  • mineral oil fractions such as kerosene or diesel oil, coal tar oils as well as oils of vegetable or animal origin
  • aliphatic, cyclic and aromatic hydrocarbons e.g. Paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alkyl
  • Solid carriers are, for example, mineral earths such as silicic acids, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate , Ureas and vegetable products such as cornmeal, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
  • mineral earths such as silicic acids, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate , Ureas and vegetable products such as cornmeal, tree
  • Surfactants are the alkali metal, alkaline earth metal, ammonium salts of aromatic sulfonic acids, e.g. Ligninsulfonic acids (eg Borrespers types, Borregaard), phenolsulfonic acids, naphthalenesulfonic acids (Morwet types, Akzo Nobel) and dibutylnaphthalenesulfonic acid (Nekal types, BASF AG), and of fatty acids, alkyl and alkylarylsulfonates, alkyl, Lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta- and octadecanols and of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthal
  • Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with a solid carrier.
  • Granules, e.g. Coating, impregnation and homogeneous granules can be prepared by binding the active compounds to solid carriers.
  • Aqueous application forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by addition to be prepared from water.
  • emulsions, pastes or oil dispersions the compounds of the formula I, especially Ia and Ib, as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agents, tackifiers, dispersants or emulsifiers.
  • concentrates consisting of active substance, wetting, adhesion, dispersing or emulsifying agent and possibly solvent or oil, which are suitable for dilution with water.
  • the concentrations of the active ingredients in the ready-to-use formulations can be varied within wide ranges.
  • the formulations generally contain from 0.001 to 98% by weight, preferably from 0.01 to 95% by weight, of at least one active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
  • compositions of the invention may be formulated as follows: 1. Products for dilution in water
  • active compound 15 parts by weight of active compound are dissolved in 75 parts by weight of an organic solvent (e.g., alkylaromatics) with the addition of Ca-dodecylbenzenesulfonate and castor oil ethoxylate (each 5 parts by weight).
  • organic solvent e.g., alkylaromatics
  • Dilution in water results in an emulsion.
  • the formulation has 15% by weight active ingredient content.
  • Dodecylbenzenesulfonate and castor oil ethoxylate (each 5 parts by weight) dissolved. This mixture is added to water by means of an emulsifying machine (e.g., Ultraturax) in 30 parts by weight and made into a homogeneous emulsion. Dilution in water results in an emulsion.
  • the formulation has an active ingredient content of 25% by weight.
  • active compound 20 parts by weight are mixed with the addition of 10 parts by weight of and wetting agents and 70 parts by weight of water or an organic solvent in an agitating ball mill to a fine Wirkstoffsus- pension comminuted. Dilution in water results in a stable suspension of the active ingredient.
  • the active ingredient content in the formulation is 20% by weight.
  • active compound 50 parts by weight of active compound are finely ground with the addition of 50 parts by weight of dispersants and wetting agents and prepared by means of industrial equipment (for example extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble granules. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the formulation has an active ingredient content of 50% by weight.
  • active compound 75 parts by weight of active compound are ground with the addition of 25 parts by weight of dispersing and wetting agents and silica gel in a rotor-Strator mill. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the active ingredient content of the formulation is 75% by weight.
  • Dispersing agent 1 part by weight of gelling agent and 70 parts by weight of water or an organic solvent milled to a fine suspension. Dilution with water results in a stable suspension with 20% by weight active ingredient content.
  • a first embodiment of the invention relates to a composition in the form of a plant protection agent formulated as a 1-component composition comprising the at least one active substance of the formula I (active ingredient A) and at least one further active ingredient selected from the herbicides B and the safeners C and a solid or liquid carrier and optionally one or more surface-active substances.
  • a second embodiment of the invention relates to composition in the form of a plant protection composition formulated as a 2-component composition
  • a first formulation containing the at least one active substance A, a solid or liquid carrier and optionally one or more surface-active substances, and a second component comprising at least one further active ingredient selected from herbicides B and safeners C, a solid or liquid carrier and optionally one or more surface-active substances.
  • the active ingredient A and the at least one further active ingredient B and / or C can be applied together or separately, at the same time or successively, before, during or after emergence of the plants.
  • the time sequence of the delivery of the active substances A, B and / or C is of secondary importance. It is only essential that the at least one active ingredient A and the at least one further active ingredient B and / or C are present at the same time at the site of action, ie. at the same time as having contact with the plant to be controlled or being ingested by it.
  • the required application rate of pure drug composition i. A and B and optionally C without formulation auxiliaries, is dependent on the composition of the plant population, on the developmental stage of the plants, on the climatic conditions at the place of use and on the application technique.
  • the application rate of A and B and optionally C is 0.001 to 3 kg / ha, preferably 0.005 to 2.5 kg / ha and in particular 0.01 to 2 kg / ha of active substance (a.S.).
  • the required application rates of compounds I are generally in the range of 0.0005 kg / ha to 2.5 kg / ha and preferably in the range of 0.005 kg / ha to 2 kg / ha or 0.01 kg / ha to 1, 5 kg / h aS
  • the required application rates of compounds B are generally in the range of 0.0005 kg / ha to 2.5 kg / ha and preferably in the range of 0.005 kg / ha to 2 kg / ha or 0.01 kg / ha to 1, 5 kg / h aS
  • the required application rates of compounds C are generally in the range of 0.0005 kg / ha to 2.5 kg / ha and preferably in the range of 0.005 kg / ha to 2 kg / ha or 0.01 kg / ha to 1, 5 kg / h aS
  • the funds are mainly supplied to the plants by foliar spraying.
  • the application can be carried out, for example, with water as a carrier by conventional spraying techniques with spray amounts of about 100 to 1000 l / ha (eg 300 to 400 l / ha).
  • An application of the herbicidal agents in the so-called "low volume” and "ultra-low-volume” method is just as possible as their application in the form of so-called microgranules.
  • the application of the compounds I or the herbicidal compositions containing them can be carried out in the pre-emergence, postemergence or together with the seed of a crop. It is also possible to apply the compositions by applying seed pretreated with a composition according to the invention to a crop. If the active substances A and B and, where appropriate, C are less compatible with certain crops, application techniques may be used in which the herbicidal products are sprayed with the help of sprayers so that the leaves of the sensitive crops are not struck if possible Active ingredients on the leaves underneath growing undesirable plants or the uncovered bottom surface arrive (post-directed, lay-by). In another embodiment, the application of the composition may be by treatment of seed.
  • the treatment of seed essentially comprises all techniques familiar to the skilled person (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping, and seed pelleting) based on the novel process Compounds of formula I or of agents produced therefrom
  • the herbicidal agents can be diluted or applied undiluted.
  • seed includes seeds of all kinds, e.g. Grains, seeds, fruits, tubers, cuttings and similar forms.
  • seed preferably describes grains and seeds here.
  • Seeds of the abovementioned crops but also the seeds of transgenic or obtained by conventional breeding methods plants can be used as seeds.
  • the application rates of active ingredient are 0.001 to 3.0 kg / ha, preferably 0.01 to 1.0 kg / ha of active substance (a.
  • the compounds I are usually used in amounts of 0.001 to 10 kg per 100 kg of seed.
  • HPLC column RP-18 column (Chromolith Speed ROD from Merck KgaA, Germany) eluent: acetonitrile + 0.1% trifluoroacetic acid (TFA) / water + 0.1% TFA in a gradient from 5:95 to 95: 5 in 5 minutes at 40 0 C, flow rate 1, 8 ml / min.
  • MS Quadrupole electrospray ionization, 80 V (positive mode)
  • Tetrahydrofuran (THF, 34 mL) was added a solution of N- (tert-butoxycarbonyl) - ⁇ -methylphenylalanine (6.3 g, 22.6 mmol) in THF (13 mL) at 0 ° C under N 2 atmosphere. The reaction mixture was stirred at room temperature for 8 h. Subsequently, ⁇ - (2-cyanophenyl) ethylalaninate hydrochloride (8.6 g, 33.8 mmol) was added portionwise followed by diisopropylethylamine (DIPEA, 8.7 g, 67.6 mmol). The reaction mixture was stirred overnight at 45 0 C and then for 2 h under reflux conditions.
  • DIPEA diisopropylethylamine
  • Part B Application examples
  • compositions according to the invention were demonstrated by greenhouse experiments:
  • the culture vessels used were plastic pots with loamy sand with about 3.0% of humus as substrate.
  • the seeds of the test plants were sown separately by species.
  • the active ingredients suspended or emulsified in water were applied directly after sowing by means of finely distributing nozzles.
  • the jars were lightly rained to promote germination and growth and then covered with clear plastic hoods until the plants had grown. This cover causes a uniform germination of the test plants, if it was not affected by the active ingredients.
  • test plants were grown depending on the growth form only to a height of from 3 to 15 cm and then treated with the suspended or emulsified in water agents.
  • the test plants were either sown directly and grown in the same containers or they were first grown separately as seedlings and transplanted into the test containers a few days before the treatment.
  • the plants were kept species-specific at temperatures of 10 - 25 ° C and 20 - 35 ° C, respectively.
  • the trial period lasted for 2 to 4 weeks. During this time, the plants were cared for, and their response to each treatment was evaluated.
  • the rating was based on a scale of 0 to 100. 100 means no emergence of the plants or complete destruction of at least the above-ground parts and 0 no damage or normal growth course.
  • a good herbicidal activity is at values of at least 70 and a very good herbicidal activity is given at values of at least 85.
  • component A and B and optionally C was formulated as 5% by weight or 100% strength by weight emulsion concentrate or a commercially available formulation of component B was used and added with the addition of that amount of solvent system into the spray mixture, with which the active ingredient was applied.
  • the solvent used in the examples was water.
  • the trial period was 20 or 21 days. During this time, the plants were cared for and their reactions to the drug treatments were recorded. The damage from the chemical agents was evaluated on a scale of 0 to 100% compared to the untreated control plants. 0 means no damage and 100 means complete destruction of the plants.
  • the plants used in the greenhouse experiments are composed of the following species:
  • a.S. active substance, based on 100% active ingredient.
  • the Colby values E are given in parentheses () in Application Examples 1 to 23.
  • Example 14 Synergistic herbicidal action of the compound from Example 20 with dimethenamid-P from group b10) in the pre-emergence process.
  • Example 20 250 + 1000 100 - 100
  • the compound 1-1 i. 2- [5-benzyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylidenemethyl] benzonitrile in the form of the Z-isomer used as a racemic mixture.
  • 2- [5-Benzyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylidenemethyl] benzonitrile in the form of the Z-isomer is also referred to below as compound 1-1 (Z).

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
EP08760878A 2007-06-12 2008-06-11 Herbizid wirksame zusammensetzung Withdrawn EP2157856A1 (de)

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Families Citing this family (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW200906805A (en) * 2007-06-12 2009-02-16 Basf Se Piperazine compounds having herbicidal action
CA2689209A1 (en) * 2007-06-12 2008-12-18 Basf Se Piperazine compounds having herbicidal action
EP2315760B1 (de) * 2008-07-29 2013-03-06 Basf Se Piperazinverbindungen mit herbizider wirkung
WO2010018067A1 (de) * 2008-08-13 2010-02-18 Basf Se Verfahren zur herstellung von piperazindion-derivaten
US20110183848A1 (en) * 2008-10-02 2011-07-28 Basf Se Piperazine Compounds With Herbicidal Effect
AR075664A1 (es) * 2008-12-09 2011-04-20 Basf Se Mezclas herbicidas
TW201024278A (en) * 2008-12-31 2010-07-01 Marrone Bio Innovations Inc Uses of thaxtomin and thaxtomin compositions as herbicides
KR101278140B1 (ko) * 2010-07-15 2013-06-27 공주대학교 산학협력단 2,5-다이케토피페라진 유도체를 활성성분으로 포함하는 농업용 약제
CN102057924B (zh) * 2011-01-13 2013-02-13 青岛瀚生生物科技股份有限公司 一种含有环苯草酮和五氟磺草胺的复配组合物
JP2013124234A (ja) * 2011-12-15 2013-06-24 Sumitomo Chemical Co Ltd サトウキビ畑の雑草防除方法
JP2013124233A (ja) * 2011-12-15 2013-06-24 Sumitomo Chemical Co Ltd サトウキビ畑の雑草防除方法
WO2013106543A2 (en) * 2012-01-12 2013-07-18 Dow Agrosciences Llc Herbicidal compositions containing bentazon and als inhibitor and accase inhibitor
BR102013025041B1 (pt) 2012-09-28 2022-11-08 Dow Agrosciences Llc Composição herbicida, e método para controlar vegetação indesejável
CN102960339A (zh) * 2012-12-11 2013-03-13 成强 抑芽丹水分散粒剂及其制备方法
CN104994738B (zh) 2012-12-12 2019-06-28 美国陶氏益农公司 施用五氟磺草胺和苯噻酰草胺所引起的协同杂草防治
LT2931045T (lt) 2012-12-14 2019-02-11 Dow Agrosciences Llc Sinergistinis piktžolių naikinimas, taikant aminopiralidą ir klopiralidą
US10412964B2 (en) 2012-12-14 2019-09-17 Dow Agrosciences Llc Synergistic weed control from applications of aminopyralid and clopyralid
BR102013032924B8 (pt) 2012-12-21 2022-10-11 Dow Agrosciences Llc Composição herbicida, e método para controle de ervas daninhas
HUE043659T2 (hu) 2012-12-21 2019-08-28 Dow Agrosciences Llc Hõmérséklet-stabil vizes klokvintocet-mexil készítmények
MX2015011043A (es) 2013-02-25 2015-10-22 Dow Agrosciences Llc Métodos para el control de malezas en plantíos de piña.
CN105578882B (zh) 2013-07-12 2018-06-12 拜耳农作物科学股份公司 包含除草活性脂肪酸和als抑制剂的除草剂组合产品
JP6452687B2 (ja) * 2013-10-25 2019-01-16 バイエル・クロップサイエンス・アクチェンゲゼルシャフト Ｎ−（１，３，４−オキサジアゾール−２−イル）−アリールカルボン酸アミド類を含んでいる除草剤組成物
US9078443B1 (en) 2014-01-31 2015-07-14 Fmc Corporation Methods for controlling weeds using formulations containing fluthiacet-methyl and HPPD herbicides
CA2968659C (en) * 2014-11-24 2023-06-13 Valent U.S.A. Llc Pyroxasulfone and glutamine synthesis inhibitor compositions for weed control
WO2016115709A1 (en) * 2015-01-22 2016-07-28 Hicap Formulations (Hong Kong) Ltd. A safe, one-shot rice herbicide composition and weed control method in rice fields
AU2016292677B2 (en) * 2015-07-10 2020-09-24 BASF Agro B.V. Herbicidal composition comprising cinmethylin and specific quinolinecarboxylic acids
BR112018002851B1 (pt) * 2015-08-12 2023-02-07 Bayer Cropscience Aktiengesellschaft Uso de aclonifen ou de um composição compreendendo aclonifen e método para controlar plantas nocivas e/ou regular crescimento de planta em plantas de cultivo de raízes tuberosas
CN105851023A (zh) * 2016-05-13 2016-08-17 创新美兰（合肥）股份有限公司 一种唑草酮、氰氟草酯和五氟磺草胺复配可分散油悬浮剂及其制备方法
CN105961421A (zh) * 2016-05-13 2016-09-28 创新美兰（合肥）股份有限公司 一种苯醚甲环唑、丙环唑和吡唑醚菌酯复配悬浮剂及其制备方法
CN105766977A (zh) * 2016-05-13 2016-07-20 创新美兰（合肥）股份有限公司 一种麦草畏、烟嘧磺隆和甲基磺草酮复配可分散油悬浮剂及其制备方法
CN106106491A (zh) * 2016-06-21 2016-11-16 创新美兰（合肥）股份有限公司 一种吡唑醚菌酯和咪鲜胺复配水乳剂及其制备方法
CN106472515A (zh) * 2016-10-13 2017-03-08 广东中迅农科股份有限公司 含有双草醚的除草组合物
CN107232192A (zh) * 2017-07-10 2017-10-10 安徽众邦生物工程有限公司 一种用于防除免耕田杂草的组合物
CN107927006A (zh) * 2017-11-27 2018-04-20 来安县义坤农业发展有限公司 一种用于蔺草的专用除草剂
CN108142428A (zh) * 2017-12-22 2018-06-12 北京科发伟业农药技术中心 含唑啉草酯和呋草酮的除草组合物
WO2020172305A1 (en) 2019-02-19 2020-08-27 Gowan Company, L.L.C. Stable liquid compositions and methods of using the same
CN113180040A (zh) * 2021-04-21 2021-07-30 南京吉星生物技术开发有限公司 一种五氟磺草胺与安全剂(吡唑解草酯)缓解其对小麦药害的组合及其应用

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63290868A (ja) * 1987-05-22 1988-11-28 Fujisawa Pharmaceut Co Ltd ジケトピペラジン誘導体およびその塩類
MXPA02006826A (es) * 2000-01-18 2004-04-05 Nereus Phamraceuticals Inc Un inhibidor de division celular y un metodo de produccion del mismo.
US20030171379A1 (en) * 2001-12-28 2003-09-11 Jacobs Robert S. Methods of treating, preventing, or inhibiting inflammation with Mactanamide compounds
AR058408A1 (es) * 2006-01-02 2008-01-30 Basf Ag Compuestos de piperazina con accion herbicida
US20090137396A1 (en) * 2006-01-05 2009-05-28 Basf Se Piperazine Compounds with a Herbicidal Action
TW200906805A (en) * 2007-06-12 2009-02-16 Basf Se Piperazine compounds having herbicidal action
CA2689209A1 (en) * 2007-06-12 2008-12-18 Basf Se Piperazine compounds having herbicidal action

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2008152074A1 *

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JP2010529170A (ja) 2010-08-26
BRPI0812954A2 (pt) 2014-10-07
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CL2008001749A1 (es) 2010-01-29
TW200911120A (en) 2009-03-16
PE20090366A1 (es) 2009-04-26
CA2690072A1 (en) 2008-12-18
WO2008152074A1 (de) 2008-12-18
EA200901658A1 (ru) 2010-06-30
AU2008263903A1 (en) 2008-12-18
CN101677540A (zh) 2010-03-24

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