WO2019228787A1 - 2-alkyle-6-alcoxyphényle-pyrroline-2-ones à substitution spéciale et leur utilisation comme herbicides - Google Patents
2-alkyle-6-alcoxyphényle-pyrroline-2-ones à substitution spéciale et leur utilisation comme herbicides Download PDFInfo
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- 0 CC#Cc1cc(O*)c(CC(NC(CC2)(CCC2O*)C(O*)=O)=O)c(*)c1 Chemical compound CC#Cc1cc(O*)c(CC(NC(CC2)(CCC2O*)C(O*)=O)=O)c(*)c1 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/54—Spiro-condensed
Definitions
- the present invention relates to novel herbicidally active 3-phenylpyrroline-2-ones according to the general formula (I) * or to agrochemically acceptable salts thereof, and to their use for controlling weeds and grass weeds in crops of useful plants.
- bicyclic 3-aryl-pyrrolidine-2,4-dione derivatives EP-A-355 599, EP-A-415 211 and JP-A-12-053 670
- Arylpyrrolidine-2,4-dione derivatives EP-A-377 893 and EP-A-442 077) having herbicidal, insecticidal or fungicidal activity.
- the object of the present invention is consequently to provide novel compounds which do not have the disadvantages mentioned.
- the present invention therefore relates to novel substituted 3-phenylpyrrolin-2-ones of the general formula (I) *, or an agrochemically acceptable salt thereof,
- R 2 is Ci-C ö alkyl or Ci-fVI laloalkyl
- Z is Ci-C ö alkyl
- G is hydrogen, a leaving group L or a cation E, where
- L is one of the following radicals
- R 3 is C 1 -C 4 -alkyl or C 1 -C 3 -alkoxy-C 1 -C -alkyl
- R 4 is C 1 -C 4 alkyl
- R 5 is C 1 -C 4 -alkyl, an unsubstituted phenyl or a phenyl which is monosubstituted or polysubstituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, nitro or cyano,
- R 6 , R 6 ' is independently methoxy or ethoxy
- R 7, R 8 are each independently methyl, ethyl, phenyl, or together form a saturated 5-, 6- or 7-membered ring, or together form a saturated 5-, 6-, or 7-membered heterocycle with an oxygen, or form sulfur atom,
- E is an alkali metal ion, an ion equivalent of an alkaline earth metal, an ion equivalent
- Hydrogen atoms are replaced by identical or different radicals from the groups C 1 -C 10 -alkyl or C 3 -C 7 -cycloalkyl, which are each independently of one another or substituted by fluorine, chlorine, bromine, cyano, hydroxyl or by one or more oxygen atoms.
- sulfur atoms may be interrupted, is a cyclic secondary or tertiary aliphatic or heteroaliphatic ammonium ion, for example Morpholinium, thiomorpholinium, piperidinium, pyrrolidinium or each protonated l, 4-diazabicyclo [1.1.2] octane (DABCO) or l, 5-diazabicyclo [4.3.0] undec-7-ene (DBU), a heteroaromatic ammonium cation, for example each protonated pyridine,
- DABCO 4-diazabicyclo [1.1.2] octane
- DBU 5-diazabicyclo [4.3.0] undec-7-ene
- Alkyl is saturated, straight-chain or branched hydrocarbon radicals having in each case the number of carbon atoms, for example C 1 -C 6 -alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methyl-propyl, 2-methylpropyl, 1,1- Dimethylethyl, pentyl, 1-methylbutyl,
- Alkyl substituted by halogen means straight-chain or branched alkyl groups, in which groups some or all of the hydrogen atoms may be replaced by halogen atoms, e.g. C 1 -C 2 -haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2, 2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro, 2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroeth
- Alkenyl means unsaturated, straight-chain or branched hydrocarbon radicals having in each case the number of carbon atoms and a double bond in any position, e.g. C2-C6 alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl,
- Cycloalkyl means a carbocyclic saturated ring system preferably having 3-8 ring C atoms, e.g. Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
- substituents wherein substituents having a double bond on the cycloalkyl, z.
- alkylidene group such as methylidene, are included.
- Alkoxy denotes saturated, straight-chain or branched alkoxy radicals with the number of carbon atoms given in each case, for example C 1 -C 6 -alkoxy, such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methyl-propoxy, 2-methylpropoxy, 1,1- Dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy,
- Methylpentoxy 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy,
- Alkoxy substituted by halogen means straight-chain or branched alkoxy radicals having the respective indicated number of carbon atoms, in which groups some or all of the hydrogen atoms may be replaced by halogen atoms as mentioned above, e.g.
- C 1 -C 2 -haloalkoxy such as chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy,
- the compounds of the formula (I) * can be present as geo metric and / or optical isomers or mixtures of isomers, in different composition, for example also in cis or trans form, which are defined as follows:
- R 1 is C 1 -C 3 -alkoxy-C 2 -C 4 -alkyl
- R 2 is C 1 -C 3 -alkyl or C 1 -C 3 -haloalkyl
- Z is C 1 -C 4 -alkyl
- G is hydrogen, a leaving group F or a cation E, where
- Ci-C 4 - alkyl or Ci-C 3 alkoxy-Ci-C 4 alkyl
- R 4 is C 1 -C 4 -alkyl
- Ci-C 4 alkyl unsubstituted phenyl or mono- or polysubstituted by halogen, C 1 -C 4 - alkyl, Ci-C 4 haloalkyl or Ci-C 4 alkoxy substituted phenyl,
- E is an alkali metal ion, an ion equivalent of an alkaline earth metal, an ion equivalent Aluminum, an ion equivalent of a transition metal, a magnesium-halogen cation or an ammonium ion, in which optionally one, two, three or all four hydrogen atoms are replaced by identical or different radicals from the groups Ci-Cio-alkyl or C 3 -C 7 -cycloalkyl, which may each independently be mono- or polysubstituted by hydroxy or halogen or interrupted by one or more oxygen atoms, or furthermore also represents a trimethylsulfonium ion.
- R 2 is methyl or ethyl
- Z is methyl or ethyl
- G is hydrogen, a leaving group L or a cation E, where
- L is one of the following radicals
- R 3 is methyl, ethyl, isopropyl, t-butyl or C 1 -C 2 -alkoxy-C 1 -C 3 -alkyl,
- R 4 is methyl or ethyl
- E is a sodium or potassium ion, an ion equivalent of calcium, magnesium or aluminum.
- R 9 is alkyl, preferably methyl or ethyl, optionally in the presence of a suitable solvent or diluent, with a suitable base with formal cleavage of the group R 9 OH cyclized, or b) a compound of the general formula (Ia) *,
- Hal is a halogen, preferably chlorine or bromine or a sulfonic acid group, optionally in the presence of a suitable solvent or diluent and a suitable base, brings to reaction.
- the precursors of the general formula (II) * can in analogy to known methods, for example by reacting an amino acid ester of the general formula (IV) * with a phenylacetic acid of the general formula (V), wherein R 1 , R 2 , R 9 and Z den the have the meaning described above, if appropriate by adding a dehydrating agent and optionally in the presence of a suitable solvent or diluent, are prepared.
- Amino esters of the general formula (IV) * are known from the literature, for example from WO 2006/000355.
- Phenylacetic acids of the general formula (V) are likewise known inter alia from WO 2015/040114 or can be prepared in analogy to processes known from the literature.
- the compounds of the formula (I) * (and / or their salts) according to the invention have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants.
- the present invention therefore also provides a method for controlling undesirable plants or for regulating the growth of plants, preferably in plant crops, wherein one or more compounds of the invention are applied to the plants (eg harmful plants such as monocotyledonous or dicotyledonous weeds or undesired crop plants), the seeds (eg grains, seeds or vegetative propagules such as tubers or sprout parts with buds) or the area on which the plants grow (eg the acreage) are applied.
- harmful plants such as monocotyledonous or dicotyledonous weeds or undesired crop plants
- the seeds eg grains, seeds or vegetative propagules such as tubers or sprout parts with buds
- the area on which the plants grow eg the acreage
- the compounds according to the invention can be applied, for example, in pre-sowing (optionally also by incorporation into the soil), pre-emergence or postemergence process.
- pre-sowing optionally also by incorporation into the soil
- postemergence process Specifically, by way of example, some representatives of the monocotyledonous and dicotyledonous weed flora can be mentioned, which can be controlled by the compounds according to the invention, without the intention of limiting them to certain species.
- the compounds according to the invention are applied to the surface of the earth before germination, either the emergence of the weed seedlings is completely prevented or the weeds grow up to the cotyledon stage stage, but then stop their growth.
- the compounds according to the invention can have selectivities in useful cultures and can also be used as nonselective herbicides.
- the active compounds can also be used for controlling harmful plants in crops of known or yet to be developed genetically modified plants.
- the transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain active ingredients used in the agricultural industry, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
- Other special properties concern e.g. the crop in terms of quantity, quality, shelf life, composition and special ingredients.
- transgenic plants with increased starch content or altered quality of the starch or those with other fatty acid composition of the crop are known.
- Other particular properties are tolerance or resistance to abiotic stressors, e.g. Heat, cold, drought, salt and ultraviolet radiation.
- the compounds of the formula (I) * can be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant.
- new plants which have modified properties in comparison to previously occurring plants consist, for example, in classical breeding methods and the production of mutants.
- new plants with altered properties can be generated by means of genetic engineering methods (see, for example, EP 0221044, EP 0131624).
- genetic modifications of crop plants have been described for the purpose of modifying the starch synthesized in the plants (eg WO 92/011376 A, WO 92/014827 A, WO 91/019806 A), transgenic crop plants which are resistant to certain glufosinate-type herbicides (US Pat.
- transgenic crops z For example, corn or soybean with the trade name or designation Optimum TM GAT TM (Glyphosate ALS Tolerant).
- transgenic crops for example cotton, having the capacity Bacillus thuringiensis To produce toxins (Bt toxins), which make the plants resistant to certain pests (EP 0142924 A, EP 0193259 A).
- Transgenic crops with modified fatty acid composition WO 91/013972 A.
- genetically modified crops with new content or secondary substances for example, new phytoalexins which cause increased disease resistance (EP 0309862 A, EP 0464461 A)
- transgenic crop plants produce pharmaceutically or diagnostically important proteins ("molecular pharming") transgenic crops that are characterized by higher yields or better quality transgenic crop plants which are characterized by a combination of the above-mentioned new properties (“gene stacking")
- nucleic acid molecules can be introduced into plasmids that allow mutagenesis or sequence alteration by recombination of DNA sequences.
- Base exchanges are made, partial sequences removed or natural or synthetic sequences added.
- For the connection of the DNA fragments with one another adapters or linkers can be attached to the fragments, see e.g. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd Ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker "Genes and Clones", VCH Weinheim 2nd edition 1996
- the production of plant cells having a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to obtain a cosuppression effect, or the expression of at least one appropriately engineered ribozyme which specifically cleaves transcripts of the above gene product.
- DNA molecules can be used which comprise the entire coding sequence of a gene product, including any flanking gene Sequences, as well as DNA molecules, which comprise only parts of the coding sequence, which parts must be long enough to cause an antisense effect in the cells. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical.
- the synthesized protein may be located in any compartment of the plant cell.
- the coding region is linked to DNA sequences which ensure localization in a particular compartment.
- sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad., U.S.A. 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).
- the expression of the nucleic acid molecules can also take place in the organelles of the plant cells.
- the transgenic plant cells can be regenerated to whole plants by known techniques.
- the transgenic plants may, in principle, be plants of any plant species, that is, both monocotyledonous and dicotyledonous plants.
- the compounds of formula (I) * according to the invention can be used in transgenic cultures which are resistant to growth factors, such as e.g. 2,4-D, dicamba or against herbicides containing essential plant enzymes, e.g. Acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or Hydoxyphenylpyruvat Dioxygenases (HPPD) inhibit or resistant to herbicides from the group of sulfonylureas, the glyphosate, glufosinate or Benzoylisoxazole and analogues, or against any combination of these agents resistant.
- growth factors such as e.g. 2,4-D, dicamba or against herbicides containing essential plant enzymes, e.g. Acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or Hydoxyphenylpyruvat Dioxygenases (HPPD) inhibit or resistant to herbicides from the group of
- the compounds according to the invention can particularly preferably be used in transgenic crop plants which are resistant to a combination of glyphosates and glufosinates, glyphosates and sulfonylureas or imidazolinones. Most preferably, the compounds of the invention in transgenic crops such. As corn or soybean with the trade name or the name OptimumTM GATTM (Glyphosate ALS Tolerant) can be used.
- the invention therefore also relates to the use of the inventive compounds of the formula (I) * as herbicides for controlling harmful plants in transgenic crop plants.
- the compounds according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules in the customary formulations.
- the invention therefore also relates to herbicidal and plant growth-regulating agents which contain the compounds according to the invention.
- the compounds according to the invention can be formulated in various ways, depending on which biological and / or chemical-physical parameters are predetermined. Possible formulation options are, for example: wettable powder (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions , Suspension concentrates (SC), oil or water based dispersions, oil miscible solutions, capsule suspensions (CS), dusts (DP), mordants, granules for litter and soil application, granules (GR) in the form of micro, spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.
- WP wettable powder
- SP water-soluble powders
- EC emulsifiable concentrates
- the formulation auxiliaries such as inert materials, surfactants, solvents and other additives are also known and are described for example in:. Watkins, “Handbook of Insecticide Dust Diluent and Carriers", 2nd Ed, Darland Books, Caldwell NJ, Hv Olphen, "Introduction to Clay Colloid Chemistry ", 2 nd Ed., J. Wiley & Sons, NY, C. Marsden,” Solvents Guide “, 2nd Ed., Interscience, NY 1963, McCutcheon's” Detergents and Emulsifiers Annual ", MC Publ. Corp. , Ridgewood NJ, Sisley and Wood, “Encyclopaedia of Surface Active Agents", Chem. Publ. Co.
- combination partners for the compounds according to the invention in mixture formulations or in the tank mix are known active compounds which are based on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II or protoporphyrinogen oxidase are based, can be used, for example from Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc.
- herbicidal mixture partners examples include:
- plant growth regulators as possible mixing partners are:
- Safeners which, in combination with the compounds of the formula (I) * according to the invention and, if appropriate, in combinations with further active compounds, such as, for example, Insecticides, acaricides, herbicides, fungicides as listed above, are preferably selected from the group consisting of:
- P A is a natural number from 0 to 5, preferably 0 to 3;
- R A 1 is halogen, (C 1 -C 4) alkyl, (C 1 -C 4) alkoxy, nitro or (C 1 -C 4) haloalkyl;
- WA is an unsubstituted or substituted divalent heterocyclic radical selected from the group consisting of the monounsaturated or aromatic five-membered heterocycles having 1 to 3 hetero ring atoms from the group N and O, where at least one N atom and at most one O atom are present in the ring, preferably one Remainder of the group (WA 1 ) to (WA 4 ),
- IU A is 0 or 1;
- RA 2 is ORA 3 , SRA 3 or NRA 3 RA 4 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group O and S, which is bonded via the N- Atom is connected to the Carbony l distr in (Sl) and unsubstituted or substituted by radicals from the group (Ci-C4) alkyl, (Ci-C4) alkoxy or optionally substituted phenyl, preferably a radical of the formula ORA 3 , NHRA 4 or NfCl Ph, in particular the formula ORA 3 ;
- RA 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 C atoms;
- RA 4 is hydrogen, (C 1 -C 6 ) alkyl, (C 1 -C 6 ) alkoxy or substituted or unsubstituted phenyl;
- RA 5 is H, (Ci-C 8 ) alkyl, (Ci-C 8 ) haloalkyl, (Ci-C 4 ) alkoxy (Ci-C 8 ) alkyl, cyano or COORA 9 , where RA 9 hydrogen, (Ci-Cs ) Alkyl, (C 1 -C 5) haloalkyl, (C 1 -C 4) alkoxy- (C 1 -C 4) alkyl, (C 1 -C 6) -hydroxyalkyl, (C 3 -C 12) cycloalkyl or tri (C 1 -C 4) -alkyl-silyl ;
- RA 6 , RA 7 , RA 8 are identical or different hydrogen, (Ci-Cs) alkyl, (Ci-Cs) haloalkyl, (C 3 -C 12) cycloalkyl or substituted or unsubstituted phenyl; preferably: a) compounds of the type of dichlorophenylpyrazoline-3-carboxylic acid (Sl a ), preferably Compounds such as 1- (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylic acid, 1- (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl- 2-pyrazoline-3-carboxylic acid ethyl ester (S 1-1) ("mefenpyr-diethyl”) and related compounds as described in WO-A-91/07874; b) Derivatives of dichlorophenylpyrazolecarboxy
- RB 1 is halogen, (C 1 -C 4) alkyl, (C 1 -C 4) alkoxy, nitro or (C 1 -C 4) haloalkyl;
- ne is a natural number of 0 to 5, preferably 0 to 3;
- R B 2 is OR B 3 , SR B 3 or NR B 3 R B 4 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group O and S, which is connected via the N-atom with the carbonyl group in (S2) and is unsubstituted or substituted by radicals from the group (C 1 -C 4) -alkyl, (C 1 -C 4) -alkoxy or optionally substituted phenyl, preferably a radical of the formula ORB 3 , NHRB 4 or NtCl Fb, in particular the formula ORB 3 ;
- RB 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 C atoms;
- RB 4 is hydrogen, (Ci-C 6 ) alkyl, (Ci-Ce) alkoxy or substituted or unsubstituted phenyl;
- TB is a (Ci or C2) alkanediyl chain which is unsubstituted or substituted by one or two (Ci-C4) alkyl radicals or by [(Ci-C3) alkoxy] carbonyl; preferably: a) compounds of the 8-quinolinoxyacetic acid type (S2 a ), preferably
- Rc 1 is (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) haloalkenyl, (C3-C7) cycloalkyl, preferably dichloromethyl;
- Rc 2, rc 3 are identical or different hydrogen, (Ci-C 4) alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) alkynyl, (C i -C 4) haloalkyl, (C 2 - alkyl C 4) haloalkenyl, (Ci-C 4) alkylcarbamoyl (Ci-C 4), (C 2 -
- Thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or Rc 2 and Rc 3 together form a substituted or unsubstituted heterocyclic ring, preferably an oxazolidine, thiazolidine, piperidine, morpholine, hexahydropyrimidine or benzoxazine ring; preferably:
- R-29148 (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S3-2), "R-28725" (3-dichloro-acetyl-2,2-dimethyl) 1, 3-oxazolidine) from Stauffer (S3-3), "Benoxacor” (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4),
- PPG-1292 N-allyl-N - [(1,3-dioxolan-2-yl) -methyl] -dichloroacetamide
- a D is S0 2 -NR D 3 -C0 or C0-NR D 3 -S0 2
- XD is CH or N
- RD 1 is CO-NR D 5 RD 6 or NHCO-RD 7 ;
- RD 2 is halogen, (C 1 -C 4) haloalkyl, (C 1 -C 4) haloalkoxy, nitro, (C 1 -C 4) -alkyl, (C 1 -C 4) -alkoxy, (C 1 -C 4) -alkylsulfonyl, (C 1 -C 4) -alkoxycarbonyl or ( Ci-C4) alkylcarbonyl;
- RD 3 is hydrogen, (C 1 -C 4) alkyl, (C 2 -C 4) alkenyl or (C 2 -C 4) alkynyl;
- RD 4 is halogen, nitro, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -haloalkoxy, (C 3 -C 6) -cycloalkyl, phenyl, (C 1 -C 4 ) -alkoxy, cyano, (ci) C 4) alkylthio, (Ci-C 4) Alkylsulfmyl, (Ci-C 4) alkylsulfonyl, (Ci- C4) alkoxycarbonyl and (Ci-C4) alkylcarbonyl;
- RD 5 is hydrogen, (C 1 -C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 5 -C 6 ) cycloalkenyl, phenyl or 3- to 6-membered heterocyclyl containing VD heteroatoms from the group consisting of nitrogen, oxygen and sulfur, where the seven latter radicals are represented by VD substituents from the group halogen, (Ci-C 6 ) alkoxy, (Ci-C 6 ) haloalkoxy, ( Ci-C 2 ) alkylsulfinyl, (Ci-C 2 ) alkylsulfonyl, (C 3 -C 6) cycloalkyl, (Ci-C4) alkoxycarbonyl, (Ci-C4) alkylcarbonyl and phenyl and in the case of cyclic radicals also
- RD 6 is hydrogen, (C I -C ⁇ ) alkyl, (C 2 -C 6) alkenyl or (C 2 -C 6) -alkynyl, where the three last-mentioned radicals are substituted by VD radicals from the group halogen, hydroxy, (C1- C4) alkyl, (Ci-C4) alkoxy and (Ci-C4) alkylthio are substituted, or
- RD 7 is hydrogen, (Ci-C4) alkylamino, di- (Ci-C4) alkylamino, (Ci-Ce) alkyl, (C3-C6) cycloalkyl, where the 2 latter radicals by VD substituents selected from the group halogen, (Ci -C4) alkoxy, (Ci-C 6 ) haloalkoxy and (Ci-C4) alkylthio and in the case of cyclic radicals are also (C 1 -C 4 ) alkyl and (Ci-C4) haloalkyl substituted; nD is 0, 1 or 2; m D is 1 or 2; VD is 0, 1, 2 or 3; Of these, preference is given to compounds of the N-acylsulfonamide type, for example of the following formula (S4 a ), which are, for example, B. are known from WO-A-97/45016
- RD 7 is (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, where the 2 last-mentioned radicals are represented by VD substituents from the group consisting of halogen, (C 1 -C 4) -alkoxy, (C 1 -C 6 ) -haloalkoxy and (C 1 -C 4) Alkylthio and in the case of cyclic radicals are also (C 1 -C 4 ) alkyl and (Ci-C4) haloalkyl substituted;
- RD 4 is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, CF 3; m D 1 or 2; VD is 0, 1, 2 or 3; such as
- Acylsulfamoylbenzoeklareamide for example, the following formula (S4 b ), for example, are known from WO-A-99/16744, eg those in which
- RD 8 and R D 9 are each independently hydrogen, (C 1 -C 8 ) alkyl, (C 3 -C 8 ) cycloalkyl, (C 3 -C 6 ) alkenyl, (C 3 -C 6 ) alkynyl, RD 4 halogen, (C 1 -CU ) Alkyl, (C 1 -C 4 ) alkoxy, CF 3 IU D 1 or 2; for example, 1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea,
- N-phenylsulfonylterephthalamides of the formula (S4 d ) which are known, for example, from CN 101838227,
- RD 4 is halogen, (C i -CU) alkyl, (C i -C 4 ) alkoxy, CF 3; mD 1 or 2;
- Cycloalkenyl - RD 5 is hydrogen, (Ci-C 6) alkyl, (C 3 -C 6) cycloalkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C 6 C 5).
- Carboxylic acid derivatives (S5) e.g.
- Dihydroxybenzoic acid 4-hydroxysalicylic acid, 4-fluorosalicyclic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A-2004/084631, WO-A-2005/015994, WO-A-2005/016001.
- RE 1 , RE 2 are each independently halogen, (Ci-C4) alkyl, (Ci-C4) alkoxy,
- a E is COORE 3 or COSRE 4
- RE 3 , RE 4 are, independently of one another, hydrogen, (C 1 -C 4 ) -alkyl, (C 2 -C 6 ) -alkenyl,
- PE 1 is 0 or 1
- P E 2 , n E 3 are independently 0, 1 or 2, preferably:
- Methyl diphenylmethoxyacetate (CAS No. 41858-19-9) (S7-1).
- RF 2 is hydrogen or (C 1 -C 4) alkyl
- R F 3 is hydrogen, (C 1 -C 8 ) alkyl, (C 2 -C 4) afkenyl, (C 2 -C 4) alkynyl, or aryl, where each of the aforementioned C-containing radicals is unsubstituted or substituted by one or more, preferably up to three, same or different radicals from the group consisting of halogen and alkoxy substituted; or their salts, preferably compounds wherein
- n F is an integer from 0 to 2
- R F 2 is hydrogen or (C 1 -C 4) alkyl
- R F 3 is hydrogen, (C 1 -C 8) alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) alkynyl, or aryl, where each of the abovementioned C-containing radicals is unsubstituted or by one or more, preferably up to three identical or different, radicals from the group consisting of halogen and alkoxy, or their salts.
- R G 1 is halogen, (Ci-G alkyl, methoxy, nitro, cyano, CF 3 , OCF 3 YG, ZG independently of one another O or S, no an integer from 0 to 4,
- RG 2 (C 1 -Cb) alkyl, (C 2 -C 6) alkenyl, (C 3 -C 6) cycloalkyl, aryl; Benzyl, halobenzyl,
- R G 3 is hydrogen or (Ci-Ce) alkyl.
- oxyimino compound type compounds known as seed dressing agents, such as e.g. B.
- Oxabetrinil ((Z) -1,3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile) (S11-1), which is known as a seed safener for millet against damage by metolachlor,
- Fluorofenim (1- (4-chlorophenyl) -2,2,2-trifluoro-1-ethanone-O- (1,3-dioxolan-2-ylmethyl) oxime) (Si l -2), which was used as seed dressing -Safener for millet is known against damage from metolachlor, and
- Cyometrinil or “CGA-43089” ((Z) -cyanomethoxyimino (phenyl) acetonitrile) (Sl l-3), which is known as a seed dressing safener for millet against damage from metolachlor.
- Isothiochromanone (S12) class agents e.g. Methyl - [(3-oxo-1H-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (CAS Reg. No. 205121-04-6) (S12-1) and related compounds of WO-A- 1998/13361.
- Naphthalene anhydride (1,8-naphthalenedicarboxylic anhydride) (S 13-1), which is known as a seed safener for corn against damage by thiocarbamate herbicides
- MG 191 (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known as safener for corn, "MG 838” (CAS Reg. No. 133993-74-5)
- CSB l-bromo-4- (chloromethylsulfonyl) benzene
- RH 1 is a (Ci-C 6 ) haloalkyl radical and RH 2 is hydrogen or halogen and
- RH 3 , RH 4 independently of one another are hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 16) -alkenyl or (C 2 -C 6 ) -alkynyl, wherein each of the last-mentioned 3 unsubstituted or by one or more radicals from the group halogen, hydroxy, cyano, (Ci-C 4 ) alkoxy, (Ci-C 4 ) haloalkoxy, (Ci-C 4 ) alkylthio, (Ci-C 4 ) alkylamino, di [(C 1 -C 4 ) alkyl] amino, [(C 1 -C 4 ) alkoxy] carbonyl, [(C 1 -C 4 ) haloalkoxy] carbonyl, (C 3 -C 6 ) cycloalkyl, which is unsubstituted or substituted, phenyl which is unsubstituted or substitute
- RH 3 is (C 1 -C 4 ) alkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 -C 6 ) alkynyloxy or (C 2 -C 4 ) haloalkoxy and
- RH 4 is hydrogen or (C 1 -C 4) -alkyl or RH 3 and RH 4 together with the directly bonded N atom form a four- to eight-membered heterocyclic ring which, in addition to the N atom, also contains further hetero ring atoms, preferably up to two further hetero ring atoms from the group N, O and S may contain and which is unsubstituted or substituted by one or more radicals from the group halogen, cyano, nitro, (C 1 -C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (Ci-C 4 ) Alkoxy, (Ci-C 4 ) haloalkoxy and (Ci-C 4 ) alkylthio is substituted means.
- Particularly preferred safeners are mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl, dichloromide and metcamifen.
- Injectable powders are preparations which are uniformly dispersible in water and contain surfactants of the ionic and / or nonionic type (wetting agents, dispersants) in addition to the active ingredient except a diluent or inert substance.
- surfactants of the ionic and / or nonionic type (wetting agents, dispersants) in addition to the active ingredient except a diluent or inert substance.
- the herbicidal active compounds are finely ground, for example, in customary apparatuses such as hammer mills, blower mills and jet mills, and mixed simultaneously or subsequently with the formulation auxiliaries.
- Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent, e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers).
- organic solvent e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents.
- alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers
- fatty acid polyglycol esters alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide / ethylene oxide condensation products
- alkyl polyethers sorbitan esters such as e.g. Sorbitan fatty acid esters or polyoxethylenesorbitan esters such as e.g. Polyoxyethylenesorbitan fatty acid ester.
- Dusts are obtained by milling the active ingredient with finely divided solids, e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
- finely divided solids e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
- Suspension concentrates may be water or oil based. They may, for example, be prepared by wet-milling by means of commercial beads and optionally adding surfactants, as described, for example, in US Pat. are already listed above for the other formulation types.
- Emulsions for example oil-in-water emulsions (EW)
- EW oil-in-water emulsions
- aqueous organic solvents and optionally surfactants such as those already listed above in the other types of formulations produce.
- Granules can either be prepared by atomizing the active ingredient on adsorptive, granulated inert material or by applying active substance concentrates by means of adhesives, e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the surface of carriers such as sand, kaolinites or granulated inert material. It is also possible to granulate suitable active ingredients in the manner customary for the production of fertilizer granules, if desired in admixture with fertilizers.
- adhesives e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils
- Water-dispersible granules are generally prepared by the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
- the agrochemical preparations generally contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of compounds according to the invention.
- the active ingredient concentration is e.g. about 10 to 90 wt .-%, the balance to 100 wt .-% consists of conventional formulation ingredients.
- the active ingredient concentration may be about 1 to 90, preferably 5 to 80 wt .-%.
- Dust-like formulations contain 1 to 30 wt .-% of active ingredient, preferably usually 5 to 20 wt .-% of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt .-% of active ingredient.
- the active ingredient content depends, in part, on whether the active compound is liquid or solid and which granulating aids, fillers, etc. are used.
- the content of active ingredient is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
- the active substance formulations mentioned optionally contain the usual ones Adhesive, wetting, dispersing, emulsifying, penetrating, preserving, antifreeze and solvents, fillers, carriers and colorants, defoamers, evaporation inhibitors and pH and viscosity influencing agents.
- the formulations present in commercial form are optionally diluted in a customary manner, e.g. for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules by means of water. Dust-like preparations, ground or scattered granules and sprayable solutions are usually no longer diluted with other inert substances before use.
- the type of herbicide used u.a. varies the required application rate of the compounds of formula (I) * and their salts. It can vary within wide limits, e.g. between 0.001 and 10.0 kg / ha or more of active substance, but is preferably between 0.005 to 5 kg / ha, more preferably in the range of 0.01 to 1.5 kg / ha, particularly preferably in the range of 0.05 to 1 kg / ha g / ha. This applies both to pre-emergence or post-emergence applications.
- Carrier means a natural or synthetic, organic or inorganic substance, with which the active ingredients for better applicability, v.a. for application to plants or plant parts or seeds, mixed or combined.
- the carrier which may be solid or liquid, is generally inert and should be useful in agriculture.
- Suitable solid or liquid carriers are: for example, ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes, solid fertilizers, water, alcohols, especially butanol, organic solvents, mineral and vegetable oils and derivatives thereof. Mixtures of such carriers can also be used.
- ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth
- ground synthetic minerals such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes, solid fertilizers, water, alcohols, especially butanol, organic solvents, mineral and vegetable oils and derivatives thereof. Mixtures of such carriers can also be used.
- solid carriers for granules are: for example, broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic rule and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stems.
- Suitable liquefied gaseous diluents or carriers are those liquids which are gaseous at normal temperature and under atmospheric pressure, for example aerosol propellants, such as halogenated hydrocarbons, as well as butane, propane, nitrogen and carbon dioxide.
- adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-like polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins, and synthetic phospholipids.
- Other additives may be mineral and vegetable oils.
- Suitable liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or dichloromethane, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
- Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
- alcohols such as butanol or glycol and their ethers and esters
- ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
- strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
- compositions of the invention may additionally contain other ingredients, such as surfactants.
- Suitable surface-active substances are emulsifying and / or foam-forming agents, dispersants or wetting agents having ionic or nonionic properties or mixtures of these surface-active substances.
- Examples thereof are salts of polyacrylic acid, salts of lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic acid esters, taurine derivatives (preferably alkyltaurates), phosphoric esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols, and derivatives of the compounds containing sulphates, sulphonates and phosphates, for example alkylarylpolyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates, protein hydrolysates, lignin-sulphite liquors and methylcellulose.
- the presence of a surfactant is necessary when one of the active ingredients and / or one of the inert carriers is not soluble in water and when applied in water.
- the proportion of surface-active substances is between 5 and 40 percent by weight of the agent according to the invention.
- Dyes such as inorganic pigments such as iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
- the active ingredients can be combined with any solid or liquid additive commonly used for formulation purposes.
- the agents and formulations according to the invention contain between 0.05 and 99% by weight, 0.01 and 98% by weight, preferably between 0.1 and 95% by weight, particularly preferably between 0.5 and 90%. Active ingredient, most preferably between 10 and 70 weight percent.
- the active compounds or compositions according to the invention as such or depending on their respective physical and / or chemical properties in the form of their formulations or the use forms prepared therefrom, such as aerosols, Kapselsus pensionen, cold mist concentrates, hot mist concentrates, encapsulated granules, fine granules, flowable concentrates for Seed treatment, ready-to-use solutions, dustable powders, emulsifiable concentrates, oil-in-water emulsions, water-in-oil emulsions, macro granules, microgranules, oil dispersible powders, oil miscible flowable concentrates, oil miscible liquids, foams, pastes , Pesticide-coated seeds, suspension concentrates, suspension-emulsion concentrates, soluble concentrates, suspensions, wettable powders, soluble powders, dusts and granules, water-soluble granules or tablets, water-soluble powders for seed treatment, wettable powders, active substance impre
- the formulations mentioned can be prepared in a manner known per se, e.g. by mixing the active compounds with at least one customary diluent, diluent or diluent, emulsifier, dispersing and / or binding or fixing agent, wetting agent, water repellent, optionally siccatives and UV stabilizers and optionally dyes and pigments, defoaming agents, preservatives , secondary thickeners, adhesives, gibberellins and other processing aids.
- compositions according to the invention comprise not only formulations which are already ready for use and which can be applied to the plant or the seed with a suitable apparatus, but also commercial concentrates which have to be diluted with water before use.
- the active compounds according to the invention can be used as such or in their (commercial) formulations and in the formulations prepared from these formulations in admixture with other (known) active substances, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, Fertilizers, safeners Semiochemicals or present.
- active substances such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, Fertilizers, safeners Semiochemicals or present.
- the treatment according to the invention of the plants and plant parts with the active ingredients or agents is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, spraying, sprinkling, vaporizing, atomizing, atomizing, sprinkling, foaming, brushing, spreading, pouring, drip irrigation and in the case of propagation material, in particular for seeds, Furthermore, by dry pickling, wet pickling, slurry pickling, encrusting, single or multi-layer wrapping, etc. It is also possible to apply the active ingredients by the ultra-low-volume method or to inject the active ingredient preparation or the active ingredient itself into the soil.
- transgenic seed As also described below, the treatment of transgenic seed with the inventive active ingredients or agents is of particular importance.
- the heterologous gene in transgenic seed may e.g. come from microorganisms of the species Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
- this heterologous gene is derived from Bacillus sp., Wherein the gene product has an activity against the European Corn Borer and / or Western Corn Rootworm.
- the heterologous gene is from Bacillus thuringiensis.
- the agent according to the invention is applied to the seed alone or in a suitable formulation.
- the seed is treated in a state that is so stable that no damage occurs during the treatment.
- the treatment of the seed can be done at any time between harvest and sowing.
- seed is used which has been separated from the plant and freed from flasks, shells, stems, hull, wool or pulp.
- seed may be used which has been harvested, cleaned and dried to a moisture content below 15% by weight.
- seed may also be used which, after drying, e.g. treated with water and then dried again.
- the amount of the agent and / or other additives applied to the seed is chosen so that germination of the seed is not impaired or the resulting plant is not damaged. This is especially important for active ingredients, which can show phytotoxic effects in certain application rates.
- the agents according to the invention can be applied directly, ie without containing further components and without being diluted. In general, it is preferable to apply the agents to the seed in the form of a suitable formulation.
- Suitable formulations and methods for seed treatment are known to those skilled in the art and are described, for example, in the following documents: US 4,272,417 A, US 4,245,432 A, US 4,808,430, US 5,876,739, US 2003/0176428 A1, WO 2002/080675 A1, WO 2002/028186 A2.
- the active compounds according to the invention can be converted into the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed coating compositions, as well as UFV formulations.
- formulations are prepared in a known manner by mixing the active ingredients with conventional additives, such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, Konser undungsstoff, secondary thickeners, adhesives, gibberellins and water ,
- conventional additives such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, Konser undungsstoff, secondary thickeners, adhesives, gibberellins and water ,
- Dyes which may be present in the seed dressing formulations which can be used according to the invention are all dyes customary for such purposes. Both water-insoluble pigments and water-soluble dyes are useful in this case. Examples which may be mentioned under the names rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1 known dyes.
- Suitable wetting agents which may be present in the seed dressing formulations which can be used according to the invention are all wetting-promoting substances customary for the formulation of agrochemical active compounds.
- Preferably used are alkylnaphthalene sulfonates, such as diisopropyl or diisobutyl naphthalene sulfonates.
- Suitable dispersants and / or emulsifiers which may be present in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds.
- Preferably usable are nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants.
- Particularly suitable nonionic dispersants are, in particular, ethylene oxide-propylene oxide, block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ethers and their phosphated or sulfated derivatives.
- Suitable anionic dispersants are, in particular, figninsulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.
- antifoams all can be used in the seed dressing formulations which can be used according to the invention be contained for formulating agrochemical active ingredients customary foam-inhibiting substances.
- agrochemical active ingredients customary foam-inhibiting substances.
- silicone defoamers and magnesium stearate are preferred.
- all substances which can be used for such purposes in agrochemical compositions can be present in the case-mimetic formulations which can be used according to the invention.
- examples include dichlorophen and Benzylalkoholhemiformal.
- Suitable secondary thickeners which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Preference is given to cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
- Suitable adhesives which may be present in the seed dressing formulations which can be used according to the invention are all customary binders which can be used in pickling agents.
- Preferably mentioned are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose.
- the seed dressing formulations which can be used according to the invention can be used either directly or after prior dilution with water for the treatment of seed of various kinds, including seed of transgenic plants. In this case, additional synergistic effects may occur in interaction with the substances formed by expression.
- the seed dressing formulations which can be used according to the invention or the preparations prepared therefrom by the addition of water
- all mixing devices customarily usable for the dressing can be considered.
- the seed is introduced into a mixer which adds the desired amount of seed dressing formulations, either as such or after prior dilution with water, and mixes until uniformly distributing the formulation on the seed ,
- a drying process follows.
- the active compounds according to the invention are suitable for good plant tolerance, favorable toxicity to warm-blooded animals and good environmental compatibility for the protection of plants and plant organs, for increasing crop yields, improving the quality of the harvested crop. They can preferably be used as crop protection agents. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
- plants which can be treated according to the invention the following main crops are mentioned: maize, soybean, cotton, Brassica oilseeds such as Brassica napus (eg canola), Brassica rapa, B. juncea (eg (field) mustard) and Brassica carinata, rice, wheat Sugar beet, cane, oats, rye, barley, millet, triticale, flax, wine and various fruits and vegetables of various botanical taxa such as Rosaceae sp.
- Brassica oilseeds such as Brassica napus (eg canola), Brassica rapa, B. juncea (eg (field) mustard) and Brassica carinata
- rice wheat Sugar beet
- cane oats
- rye rye
- barley millet
- pome fruits such as apple and pear, but also drupes such as apricots, cherries, almonds and peaches and soft fruits such as strawberries
- Ribesioidae sp. Juglandaceae sp.
- Betulaceae sp. Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (for example, banana trees and plantations), Rubiaceae sp.
- Theaceae sp. for example, coffee
- Theaceae sp. Sterculiceae sp.
- Rutaceae sp. for example, lemons, organs and grapefruit
- Solanaceae sp. for example, tomatoes, potatoes, peppers, eggplants
- Liliaceae sp. Compositae sp.
- lettuce, artichoke and chicory - including root chicory, endive or common chicory for example, Umbelliferae sp.
- Umbelliferae sp. for example, carrots, parsley, celery and celeriac
- Cucurbitaceae sp. for example cucumber - including gherkin, squash, watermelon, gourd and melons
- Cruciferae sp. for example, white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pak choi, kohlrabi, radishes, horseradish, cress and Chinese cabbage
- Leguminosae sp. for example, peanuts, peas, and beans - such as barley bean and field bean
- Chenopodiaceae sp. for example, Swiss chard, fodder beet, spinach, beetroot), Malvaceae (for example okra), asparagaceae (for example asparagus); Useful plants and ornamental plants in the garden and forest; and each genetically modified species of these plants.
- plants and their parts can be treated.
- wild-occurring or by conventional biological breeding methods such as crossing or protoplast fusion obtained plant species and Pflan censorten and their parts are treated.
- transgenic plants and plant cultivars obtained by genetic engineering if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated.
- the term "parts” or “parts of plants” or “plant parts” has been explained above. It is particularly preferred according to the invention to treat plants of the respective commercially available or in use plant cultivars. Plant varieties are understood as meaning plants having new traits which have been bred by conventional breeding, by mutagenesis or by recombinant DNA techniques. These may be varieties, breeds, biotypes and genotypes.
- the treatment method of the invention may be used for the treatment of genetically modified organisms (GMOs), e.g. As plants or seeds are used.
- GMOs genetically modified organisms
- Genetically modified plants are plants in which a heterologous gene has been stably integrated into the genome.
- heterologous gene essentially means a gene that is provided or assembled outside the plant and which, upon introduction into the nuclear genome, chloroplast genome or mitochondrial genome, imparts new or improved agronomic or other properties to the expressed plant protein or polypeptide, or to another gene encoding it the plant is present or other genes present in the plant, down-regulated or switched off (for example by means of antisense technology, cosuppression technology or RNAi technology [RNA interference]).
- a heterologous gene present in the genome is also referred to as a transgene.
- a transgene, which is defined by its specific Vorhegen in the plant genome, is referred to as a transformation or transgenic event.
- the treatment according to the invention can also lead to superadditive (“synergistic”) effects.
- the following effects are possible, which go beyond the expected effects: reduced application rates and / or extended spectrum of action and / or increased efficacy of the active ingredients and compositions that can be used according to the invention, better plant growth, increased tolerance to high or low Temperatures, increased tolerance to drought or water or soil salt content, increased flowering, emollient, maturing, higher yields, larger fruits, greater plant height, intense leaf green color, earlier flowering, higher quality and / or higher nutritional value of the encearies, higher sugar concentration in the fruits, better storage and / or processability of the harvested products.
- Plants and plant varieties which are preferably treated according to the invention include all plants which have genetic material conferring on these plants particularly advantageous, useful features (whether obtained by breeding and / or biotechnology).
- nematode-resistant plants are e.g. following US patent applications: 11 / 765,491, 11 / 765,494, 10 / 926,819, 10 / 782,020, 12 / 032,479, 10 / 783,417,
- Plants that can be treated according to the invention are hybrid plants that already express the properties of the heterosis or the hybrid effect, which generally leads to higher yields, higher vigor, better health and better resistance to biotic and abiotic stress factors.
- Such plants are typically produced by crossing an inbred male sterile parental line (the female crossover partner) with another inbred male fertile parent line (the male crossbred partner).
- the hybrid seed is typically harvested from the male sterile plants and sold to propagators.
- Pollen sterile plants can sometimes be produced (eg in maize) by delaving (ie mechanical removal of the male reproductive organs or the male flowers); however, it is more common for male sterility to be due to genetic determinants in the plant genome.
- a ribonuclease such as a barnase is selectively expressed in the tapetum cells in the stamens.
- the fertility can then be restorated by expression of a ribonuclease inhibitor such as barstar in the tapetum cells.
- Plants or plant varieties obtained by methods of plant biotechnology, such as genetic engineering which can be treated according to the invention are herbicide-tolerant plants, i. H. Plants tolerant to one or more given herbicides. Such plants can be obtained either by genetic transformation or by selection of plants containing a mutation conferring such herbicide tolerance.
- Herbicide-tolerant plants are, for example, glyphosate-tolerant plants, ie plants that have been tolerated to the herbicide glyphosate or its salts. Plants can be made tolerant to glyphosate by various methods. Thus, for example, glyphosate-tolerant plants can be obtained by transforming the plant with a gene encoding the enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS). Examples of such EPSPS genes are the AroA gene (mutant CT7) of the bacterium Salmonella Typhimurium (Comai et al., 1983, Science 221, 370-371), the CP4 gene of the bacterium Agrobacterium sp.
- EPSPS 5-enolpyruvylshikimate-3-phosphate synthase
- Glyphosate-tolerant plants can also be obtained by expressing a gene encoding a glyphosate acetyltransferase enzyme. Glyphosate-tolerant plants can also be obtained by selecting plants containing naturally-occurring mutations of the above mentioned genes. Plants expressing EPSPS genes conferring glyphosate tolerance are described. Plants which confer other glyphosate tolerance genes, eg decarboxylase genes, are described.
- herbicide-resistant plants are, for example, plants which have been tolerated to herbicides which inhibit the enzyme glutamine synthase, such as bialaphos, phosphinotricin or glufosinate.
- Such plants can be obtained by expressing an enzyme which detoxifies the herbicide or a mutant of the enzyme glutamine synthase, which is resistant to inhibition.
- an effective detoxifying enzyme is, for example, an enzyme encoding a phosphinotricin acetyltransferase (such as the bar or pat protein of Streptomyces species). Plants expressing an exogenous phosphinotricin acetyltransferase have been described.
- hydroxyphenylpyruvate dioxygenase HPPD
- HPPD hydroxyphenylpyruvate dioxygenase
- the hydroxyphenylpyruvate dioxygenases are enzymes that catalyze the reaction in which para-hydroxyphenylpyruvate (HPP) is converted to homogentisate.
- Plants tolerant to HPPD inhibitors can be transformed with a gene encoding a naturally occurring resistant HPPD enzyme or a gene encoding a mutant or chimeric HPPD enzyme, as in WO 96/38567 , WO 99/24585, WO 99/24586, WO 2009/144079, WO 2002/046387 or US 6,768,044.
- Tolerance to HPPD inhibitors can also be achieved by transforming plants with genes encoding certain enzymes that allow the formation of homogentisate despite inhibition of the native HPPD enzyme by the HPPD inhibitor. Such plants are described in WO 99/34008 and WO 02/36787.
- the tolerance of plants to HPPD inhibitors can also be improved by adding plants in addition to a gene that is suitable for HPPD-tolerant enzyme is transformed with a gene encoding a prephenate dehydrogenase enzyme, as described in WO 2004/024928.
- plants can be made even more tolerant to HPPD inhibitors by incorporating into their genome a gene encoding an enzyme that metabolizes or degrades HPPD inhibitors, such as CYP450 enzymes (see WO 2007/103567 and WO 2008/150473 ).
- ALS inhibitors include sulfonylurea, imidazolinone, triazolopyrimidines, pyrimidinyloxy (thio) benzoates and / or sulfonylaminocarbonyltriazolinone herbicides.
- ALS also known as acetohydroxy acid synthase, AHAS
- AHAS acetohydroxy acid synthase
- plants which are tolerant of imidazolinones and / or sulfonylureas can be obtained by induced mutagenesis, selection in cell cultures in the presence of the herbicide or by mutation breeding (cf., for example, for soybean US 5,084,082, for rice WO 97/41218, for sugar beet US 5,773,702 and WO 99/057965, for salad US 5,198,599 or for sunflower WO 01/065922).
- Plants or plant varieties are tolerant to abiotic stressors. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such stress resistance.
- Particularly useful plants with stress tolerance include the following: a. Plants containing a transgene capable of reducing the expression and / or activity of the poly (ADP-ribose) polymerase (PARP) gene in the plant cells or plants. b. Plants containing a stress tolerance enhancing transgene capable of reducing the expression and / or activity of the PARC-encoding genes of the plants or plant cells; c.
- Plants which contain a stress-promoting transgene encoding a plant-functional enzyme of the nicotinamide adenine dinucleotide salvage biosynthesis pathway including nicotinamidase, nicotinate phosphoribosyltransferase, nicotinic acid mononucleotide adenyltransferase, Nicotinamide adenine dinucleotide synthetase or nicodnamide phosphoribosyltransferase.
- Plants or plant cultivars obtained by plant biotechnology methods such as genetic engineering which can also be treated according to the invention have an altered quantity, quality and / or storability of the enceary product and / or altered properties of certain components of the enceary product; such as:
- Transgenic plants that synthesize non-starch carbohydrate polymers or non-starch carbohydrate polymers whose properties are altered compared to wild-type plants without genetic modification.
- Examples are plants that produce polyfmctose, particularly the inulin and levan type, plants that produce alpha-1,4-glucans, plants that produce alpha-l, 6-branched alpha-1,4-glucans, and plants that produce Produce alternan.
- Transgenic plants or hybrid plants such as onions with certain properties such as "high soluble solids content", low pungency (LP) and / or long storage (LS) ).
- Plants or plant varieties are plants such as cotton plants with altered fiber properties. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered fiber properties; These include: a) plants such as cotton plants containing an altered form of cellulose synthase genes; b) plants such as cotton plants containing an altered form of rsw2 or rsw3 homologous nucleic acids, such as cotton plants having increased expression of sucrose phosphate synthase; c) plants such as cotton plants with increased expression of sucrose synthase; d) plants such as cotton plants in which the timing of the passage control of the Plasmodesmen is changed at the base of the fiber cell, z.
- Plants or plant varieties which can also be treated according to the invention are plants such as oilseed rape or related Brassica plants with altered oil composition properties.
- Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered oil properties; These include: a) plants, such as rape plants, that produce oil with a high oleic acid content; b) plants such as oilseed rape plants, which produce oil with a low linolenic acid content. c) plants such as rape plants that produce oil with a low saturated fatty acid content.
- Plants or plant varieties which can be obtained by plant biotechnology methods such as genetic engineering), which can also be treated according to the invention, are plants such as potatoes which are virus-resistant, e.g. against the potato virus Y (Event SY230 and SY233 from Tecnoplant, Argentina), or which are resistant to diseases such as potato late blight (eg RB gene), or which show a reduced cold-induced sweetness (which the genes Nt- Inh, II-INV) or which show the dwarf phenotype (gene A-20 oxidase).
- viruses which are virus-resistant, e.g. against the potato virus Y (Event SY230 and SY233 from Tecnoplant, Argentina), or which are resistant to diseases such as potato late blight (eg RB gene), or which show a reduced cold-induced sweetness (which the genes Nt- Inh, II-INV) or which show the dwarf phenotype (gene A-20 oxidase).
- viruses which are virus-resistant, e.g. against
- Plants or plant varieties obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, are plants such as oilseed rape or related Brassica plants with altered seed shattering properties. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered properties, and include plants such as oilseed rape with delayed or reduced seed failure.
- transgenic plants which can be treated according to the invention are Plants with transformational events or combinations of transformational events that are the subject of issued or pending petitions for non-regulated status in the United States Animal and Plant Health Inspection Service (APHIS) of the United States Department of Agriculture (USDA).
- APIS United States Animal and Plant Health Inspection Service
- USA United States Department of Agriculture
- the information is available at any time from APHIS (4700 River Road Riverdale, MD 20737, USA), for example via the website http://www.aphis.usda.gov/brs/not_reg.html.
- APHIS had either given or is pending petitions with the following information:
- Transformation events can be found in the individual petition document available from APHIS on the website via the petition number. These descriptions are hereby incorporated by reference.
- APHIS Documente various documents that may be published by APHIS regarding the petition or may be obtained from APHIS upon request.
- transgenic plants which can be treated according to the invention are plants with one or more genes coding for one or more toxins, the transgenic plants offered under the following commercial names: YIELD GARD® (for example maize, cotton, Soybeans), KnockOut® (for example corn), BiteGard® (for example maize), BT-Xtra® (for example maize), StarLink® (for example corn), Bollgard® (cotton), Nucotn® (cotton), Nucotn 33B® (cotton), NatureGard® (for example corn), Protecta® and NewLeaf® (potato).
- YIELD GARD® for example maize, cotton, Soybeans
- KnockOut® for example corn
- BiteGard® for example maize
- BT-Xtra® for example maize
- StarLink® for example corn
- Bollgard® cotton
- Nucotn® cotton
- Nucotn 33B® cotton
- NatureGard® for example corn
- Protecta® and NewLeaf® pot
- Herbicide-tolerant crops to be mentioned include, for example, corn, cotton and soybean varieties sold under the following tradenames: Roundup Ready® (glyphosate tolerance, for example corn, cotton, soybean), Liberty Link® (phosphinotricin tolerance, for example rapeseed), IMI® (imidazolinone tolerance) and SCS® (sylphonylurea tolerance), for example maize.
- Herbicide-resistant plants (plants traditionally grown for herbicide tolerance) to be mentioned include the varieties sold under the name Clearfield® (for example corn). The following examples additionally illustrate the present invention.
- a dust is obtained by mixing 10 parts by weight of a compound of the formula (I) * and / or salts thereof and 90 parts by weight of talc as an inert substance and comminuting in a hammer mill.
- a wettable powder readily dispersible in water is obtained by reacting 25 parts by weight of a compound of the formula (I) * and / or its salts, 64 parts by weight of kaolin-containing quartz as inert material, 10 parts by weight of lignosulfonic acid potassium and 1 part by weight of oleoylmethyltaurine acid Mix sodium as a wetting agent and dispersant and mill in a pin mill.
- a dispersion concentrate readily dispersible in water is obtained by reacting 20 parts by weight of a compound of the formula (I) * and / or salts thereof with 6 parts by weight of alkylphenol polyglycol ether ( ⁇ Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range, for example, about 255 to about 277 C) and milled in a ball mill to a fineness of less than 5 microns.
- An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I) * and / or salts thereof, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier.
- a water-dispersible granule is obtained by reacting 75 parts by weight of a compound of the formula (I) * and / or salts thereof,
- a water-dispersible granules are also obtained by 25 parts by weight of a compound of the formula (I) * and / or salts thereof,
- Seeds of monocotyledonous or dicotyledonous weed or crop plants are laid out in sandy loam in wood fiber pots and covered with soil.
- the compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then applied to the surface of the cover soil as an aqueous suspension or emulsion having a water application rate of 600 to 800 Eha with the addition of 0.2% wetting agent.
- the compounds according to the invention have a good herbicidal pre-emergence activity against a broad spectrum of grass weeds and weeds.
- the compounds at an application rate of 80 g / ha each show an 80-100% action against, inter alia, Alopecurus myosuroides, Avena fatua, Echinochloa crus-galli, Lolium multiflorum and Setaria viridis.
- the compounds according to the invention are therefore suitable in the pre-emergence process for controlling unwanted plant growth.
- Seeds of monocotyledonous or dicotyledonous crops are laid out in sandy loam soil in wood fiber pots, covered with soil and grown in the greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants are treated in the single leaf stage.
- the compounds according to the invention have a good herbicidal postemergence activity against a broad spectrum of grass weeds and weeds.
- the examples listed at an application rate of 80 g / ha show an 80-100% action, inter alia, against Alopecurus myosuroides, Avena fatua, Echinochloa crus galli, Lolium multiflorum and Setaria viridis.
- the compounds according to the invention are therefore suitable postemergence for controlling unwanted plant growth.
Abstract
L'invention concerne de nouvelles 3-phénylpyrroline-2-ones, à action herbicide, de formule générale (I) ou des sels agrochimiquement acceptables de celles-ci, ainsi que leur utilisation pour lutter contre les plantes adventices et les mauvaises herbes dans des cultures de plantes utiles.
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EP18174680.1 | 2018-05-29 | ||
EP18174680 | 2018-05-29 |
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PCT/EP2019/062170 WO2019228787A1 (fr) | 2018-05-29 | 2019-05-13 | 2-alkyle-6-alcoxyphényle-pyrroline-2-ones à substitution spéciale et leur utilisation comme herbicides |
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AR (1) | AR115391A1 (fr) |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2021239673A1 (fr) | 2020-05-27 | 2021-12-02 | Bayer Aktiengesellschaft | Pyrroline-2-ones substituées et leur utilisation en tant qu'herbicides |
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