DE102007029603A1 - Phenylamidine for herbicide agent, controlling unwanted plants, and for use as herbicides, comprises general formula - Google Patents

Phenylamidine for herbicide agent, controlling unwanted plants, and for use as herbicides, comprises general formula

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Publication number
DE102007029603A1
DE102007029603A1 DE102007029603A DE102007029603A DE102007029603A1 DE 102007029603 A1 DE102007029603 A1 DE 102007029603A1 DE 102007029603 A DE102007029603 A DE 102007029603A DE 102007029603 A DE102007029603 A DE 102007029603A DE 102007029603 A1 DE102007029603 A1 DE 102007029603A1
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Germany
Prior art keywords
ch
phenyl
alkyl
gt
alkoxy
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DE102007029603A
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German (de)
Inventor
Mark Wilhelm Dr. Drewes
Ralf Dr. Dunkel
Dieter Dr. Feucht
Jörg Nico Dr. Greul
Oliver Dr. Guth
Benoit Dr. Hartmann
Martin Hills
Harald Dr. Jakobi
Heinz Dr. Kehne
Birgit Dr. Kuhn
Klaus Dr. Kunz
Thomas Dr. Müller
Christopher Dr. Rosinger
Dirk Schmutzler
Thomas Dr. Seitz
Jörg Dr. Tiebes
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Bayer CropScience AG
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Bayer CropScience AG
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Priority to DE102007029603A priority Critical patent/DE102007029603A1/en
Priority claimed from EP20080716203 external-priority patent/EP2136627B1/en
Priority claimed from BRPI0808734 external-priority patent/BRPI0808734A2/en
Priority claimed from US12/530,767 external-priority patent/US20100167926A1/en
Priority claimed from CN 200880008092 external-priority patent/CN101636082B/en
Priority claimed from EP08716205.3A external-priority patent/EP2120558B1/en
Priority claimed from CN 200880008189 external-priority patent/CN101631462B/en
Publication of DE102007029603A1 publication Critical patent/DE102007029603A1/en
Application status is Withdrawn legal-status Critical

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Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES, AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, 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
    • A01N37/52Biocides, 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 groups, e.g. carboxylic acid amidines
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES, AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES, AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/781,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES, AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms

Abstract

The N 2>-phenylamidine comprises general formula (I). The N 2>-phenylamidine having general formula (I), is new. R 2>and R 3>1-6C alkyl, 3-6C cycloalkyl, cyclopropyl, iso-propyl, 2-6C alkenyl, 2-6C alkinyl, halogen-1-6C-alkenyl, halogen-1-6C-alkinyl, 1-4C-alkoxy-1-6C-alkyl, 1-4C-alkoxy-1-6C-alkenyl or 1-4C-alkoxy-2-6C-alkinyl or (CH 2) 4or (CH 2) 5, 5 or 6 membered saturated, partly saturated, unsaturated or aromatic ring; R 4>and R 5>1-6C alkyl, 2-6C alkenyl, 3-6C cycloalkyl, halogen, cyano, hydroxy, mercapto, acyl, OR 1>5, SR 1>5, Si(R 1>5) 3, halogen-1-6C-alkyl, 1-4C-alkoxy-1-6C-alkyl or heterocyclic carbon bounded to a phenyl, where R 1>5=1-8C alkyl; R 6>halogen, cyano, phenoxy, 1-8Calkylcarbonyl, 1-8C alkoxycarbonyl, 1-8C alkyl, 1-8C alkoxy, 2-8C alkenyl, 2-8C alkinyl, halogen-1-4C alkyl substituted of pyridinyl, thiadiazolyl or thiazolyl, 1,3-dioxolane substituted carbocyclic or heterocyclic, where the residue is 1-8C alkyl, 1-8C alkoxy, 2-8C alkenyl or 2-8C alkinyl; and A : -O-, -S-, -CH 2>CH 2>-, -CH 2>, -OCH 2>, -C?=C-, -NH-CO-, -N(CH 3>), -NH-, -O-CO-NH-, -S(O)n-, -NR 9>, -CR 7>=CR 7>-, -C=C-, -A 1>-, -A 1>-A 1>-, -A 2>-, -A 3>-, -A 1>O-, -A 1>S(O) n-, -OA 2>-, -NR 9>-A 2>-, -OA 2>-A 1>-, -OA 2>-CR 7>=CR 8>-, -S(O) n-A 1>-, -(CH 2) 2-ON=CR 8>-, -X-A 2>-NH-, -C(R 8>)=NO-(1-6C)-alkyl or -O(A 1>) kO-, where A 1>=-CHR 7>-, A 2>=-C(=X)-, A 3>=-CR 8>=NO-, X=O or S, R 7>=H, halogen, cyano, hydroxy, mercapto, halogen-1-6C alkyl or 1-4C-alkoxy-1-6C alkyl, R 8>=H, 1-6C alkyl, 2-6C alkenyl, 2-6C alkinyl, 1-6C alkoxy, 1-6C alkylthio, 3-6C cycloalkyl, phenyl, halogen, cyano, hydroxy, mercapto, halogen-1-6C alkyl, 1-4C alkoxy-1-6C alkyl, carbocyclic or heterocyclic, R 9>=H, 1-6C alkyl, carbocyclic or heterocyclic, k=1-3, n=0-2 and p=1-3. An independent claim is also included for a method for controlling unwanted plants, which involves applying N 2>-phenylamidine compound. [Image] ACTIVITY : Herbicide. MECHANISM OF ACTION : None given.

Description

  • The The invention relates to the technical field of herbicides, in particular that of herbicides for the selective control of weeds and grass weeds in crops.
  • It is already known from various publications that certain phenylamidines have fungicidal properties. So be in EP 1 150 944 B1 fungicidally active N 2 -phenylamidines described which carry on the phenyl ring - inter alia - a carbocyclic or heterocyclic radical bonded directly or via a mono- or polyatomic group.
  • The herbicidal activity of such compounds has not been described.
  • task The present invention was the provision of herbicidally active Links.
  • It has now been found that N 2 -phenylamidines of the formula (I), or salts thereof, have excellent herbicidal properties.
  • An object of the present invention is the use of compounds of formula (I), or salts thereof, as herbicides
    Figure 00010001
    wherein
    R 2 and R 3 are each independently (C 1 -C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, halo (C 1 -C 6 ) alkyl , Halo (C 2 -C 6 ) alkenyl, halo (C 2 -C 6 ) alkynyl, (C 1 -C 4 ) alkoxy (C 1 -C 6 ) alkyl, (C 1 -C 4 ) alkoxy (C 2 -C 6 ) alkenyl, (C 1 -C 4 ) alkoxy (C 2 -C 6 ) alkynyl,
    or R 2 and R 3 together are (CH 2 ) 4 or (CH 2 ) 5 ,
    or
    R 2 and R 3 , together with the nitrogen atom to which they are attached, form a 5- or 6-membered saturated, partially saturated, unsaturated or aromatic ring containing k heteroatoms from the group consisting of oxygen, nitrogen and sulfur, and represented by p Radicals from the group halogen, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, nitro, cyano and hydroxy is substituted,
    R 4 and R 5 are each independently (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl , Halogen, cyano, hydroxy, mercapto, acyl, OR a , SR a , Si (R a ) 3 halo (C 1 -C 6 ) alkyl, (C 1 -C 4 ) alkoxy (C 1 -C 6 ) -alkyl or heterocyclyl bonded via a carbon atom to phenyl,
    R a is (C 1 -C 8 ) -alkyl,
    m is 0, 1, 2 or 3,
    R 6 in each case by n radicals from the group halogen, cyano, phenoxy, (C 1 -C 8 ) -alkylcarbonyl, (C 1 -C 8 ) -alkoxycarbonyl, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) alkoxy, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl and 1,3-dioxolan-2yl substituted carbocyclyl or heterocyclyl, wherein said radicals are (C 1 -C 8 ) alkyl , (C 1 -C 8 ) -alkoxy, (C 2 -C 8 ) -alkenyl and (C 2 -C 8 ) -alkynyl are substituted by n radicals from the group consisting of (C 1 -C 8 ) -alkoxy, hydroxy and halogen are,
    and 1,3-dioxolan-2y is substituted by n radicals (C 1 -C 8 ) -alkyl,
    A denotes a bond or a divalent group -O-, -S (O) n -, -NR 9 , -CR 7 = CR 7 -, -C≡C-, -A 1 -, -A 1 -A 1 - , -A 2 -, -A 3 -, -A 1 O-, -A 1 S (O) n -, -OA 2 -, -NR 9 -A 2 -, -OA 2 -A 1 -, -OA 2 -CR 7 = CR 8 -, -S (O) n -A 1 -, - (CH 2 ) 2 -ON = CR 8 -, -XA 2 -NH-, -C (R 8 ) = NO- ( C 1 -C 6 ) -alkyl or -O (A 1 ) k O-,
    A 1 means -CHR 7 -,
    A 2 is -C (= X) -,
    A 3 is CR 8 = NO-,
    X is oxygen or sulfur,
    R 7 is hydrogen, halogen, cyano, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cyclo-alkyl, phenyl, halogen, cyano, hydroxyl, mercapto, halogen- (C 1 -C 6 ) alkyl or (C 1 -C 4 ) alkoxy (C 1 -C 6 ) alkyl,
    R 8 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkylthio, (C 3 -C 6 ) -cycloalkyl, phenyl, halogen, cyano, hydroxy, mercapto, halo (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ), carbocyclyl or heterocyclyl,
    R 9 is hydrogen, (C 1 -C 6 ) -alkyl, carbocyclyl or heterocyclyl,
    k is 1, 2 or 3,
    n is 0, 1 or 2, and
    p is 0, 1, 2 or 3.
  • The linkage of A with R 6 and the phenyl ring should be understood to mean that R 6 is attached to the right and the phenyl ring to the left of A.
  • The Compounds of formula (I) may also be in salt form, for example as hydrochloride or in the form of other acid adducts. These salts are also suitable as herbicides and are intended by To be encompassed formula (I). Preference is given to hydrochlorides, hydrobromides, Trifluoroacetates, acetates and trifluoromethanesulfonates.
  • In Formula (I) and all subsequent formulas may be alkyl radicals be more straight or branched with more than two carbon atoms. Alkyl radicals mean, for. Methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyl, hexyl, such as n-hexyl, i-hexyl and 1,3-dimethylbutyl. Halogen is fluorine, chlorine, bromine or iodine.
  • is a group several times substituted by radicals, so is among them Understand that this group by one or more same or different of said radicals is substituted.
  • heterocyclyl means a saturated, unsaturated or heteroaromatic cyclic residue; it contains an or several heteroatoms in the ring, preferably from the group N, O and S; preferably it is an aliphatic heterocyclyl radical with 3 to 7 ring atoms or a heteroaromatic radical with 5 or 6 ring atoms and contains 1, 2 or 3 heteroatoms. The heterocyclic Rest can z. B. a heteroaromatic radical or ring (heteroaryl) be like B. a mono-, bi- or polycyclic aromatic System in which at least one ring contains one or more heteroatoms, for example pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, Thienyl, thiazolyl, oxazolyl, furyl, pyrrolyl, pyrazolyl and imidazolyl, or is a partially or fully hydrogenated radical such as oxiranyl, pyrrolidyl, piperidyl, piperazinyl, dioxolanyl, morpholinyl, Tetrahydrofuryl. As substituents for a substituted heterocyclic radical are the substituents mentioned below in question, in addition also oxo. The oxo group can also on the hetero ring atoms, which exist in different oxidation states can, for. B .. at N and S, occur.
  • carbocyclyl means a saturated, unsaturated or aromatic cyclic radical containing exclusively carbon atoms contains in the ring; for example, cycloalkyl, cycloalkenyl, Phenyl and naphthyl. As substituents for carbocyclyl are the substituents mentioned below in question, in addition also oxo. The oxo group can also be attached to the hetero ring atoms in different oxidation states may exist, for. B. at N and S, occur.
  • cycloalkyl means a carbocyclic, saturated ring system with three to nine carbon atoms, z. As cyclopropyl, cyclopentyl or cyclohexyl.
  • So far in this specification the term acyl radical is used this the rest of an organic acid, formally through Cleavage of an OH group arises from the organic acid, z. B .. the residue of a carboxylic acid and radicals derived therefrom Acids such as the thiocarboxylic acid, optionally N-substituted Iminocarboxylic acids or the residues of carbonic acid monoesters, optionally N-substituted carbamic acids, sulfonic acids, Sulfinic acids, phosphonic acids, phosphinic acids.
  • An acyl radical is preferably formyl or acyl from the group CO-R z , CS-R z , CO-OR z , CS-OR z , CS-SR z , SOR z or SO 2 R z , where R z are each a C 1 -C 10 hydrocarbon radical such as C 1 -C 10 alkyl or phenyl which is unsubstituted or substituted, for. B .. by one or more substituents from the group halogen such as F, Cl, Br, I, alkoxy, haloalkoxy, hydroxy, amino, nitro, cyano or alkylthio, or R z denotes aminocarbonyl or aminosulfonyl, where the last two radicals unsubstituted, N-monosubstituted or N, N-disubstituted, for. B. by substituents from the group alkyl or aryl.
  • Acyl is, for example, formyl, haloalkylcarbonyl, alkylcarbonyl, such as (C 1 -C 4 ) alkylcarbonyl, phenylcarbonyl, where the phenyl ring may be substituted, or alkyloxycarbonyl, such as (C 1 -C 4 ) alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, such as (C 1 -C 4 ) alkylsulfonyl, alkylsulfinyl, such as C 1 -C 4 (alkylsulfinyl), N-alkyl-1-iminoalkyl, such as N- (C 1 -C 4 ) -1-imino (C 1 -C 4 ) alkyl and other residues of organic acids.
  • The compounds of the general formula (I) and their salts may vary depending on the type and linkage the substituents are present as stereoisomers. For example, if one or more asymmetric carbon atoms are present, enantiomers and diastereomers may occur. Stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods, for example by chromatographic separation methods. Similarly, stereoisomers can be selectively prepared by using stereoselective reactions using optically active sources and / or adjuvants. The invention also relates to all stereoisomers and mixtures thereof which include but are not specifically defined by the general formula (I). In particular, it relates to the E / Z isomers both their mixture as well as the individual isomers.
  • Preference is given to compounds of the general formula (I) in which
    R 2 and R 3 are each independently (C 1 -C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, halo (C 1 -C 6 ) alkyl , Halo (C 2 -C 6 ) alkenyl, halo (C 2 -C 6 ) alkynyl, (C 1 -C 4 ) alkoxy (C 1 -C 6 ) alkyl, (C 1 -C 4 ) alkoxy (C 2 -C 6 ) alkenyl, (C 1 -C 4 ) alkoxy (C 2 -C 6 ) alkynyl, (CH 2 ) 4 or (CH 2 ) 5 ,
    R 4 is (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl or (C 1 -C 4 ) -alkoxy (C 1 -C 6 ) -alkyl,
    R 5 is halogen, (C 1 -C 6 ) -alkyl, halogen (C 1 -C 6 ) -alkyl or (C 1 -C 4 ) -alkoxy- (C 1 -C 6 ) -alkyl,
    A is a bond, -O-, -S-, -CH 2 CH 2 -, -CH 2 -, -OCH 2 -, -CH = CH-, -C≡C-, -NH-CO-, -N (CH 3 ) -, NH- or -O-CO-NH-,
    R 6 means by n radicals from the group halogen, cyano, phenoxy, (C 1 -C 4 ) -alkylcarbonyl, (C 1 -C 4 ) -alkyl, (C 1 -C 6 ) -alkoxy, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl and 1,3-dioxolan-2yl substituted phenyl or naphthyl, where the radicals mentioned are (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy , (C 2 -C 6 ) -alkenyl and (C 2 -C 6 ) -alkynyl are substituted by n radicals from the group consisting of (C 1 -C 4 ) -alkoxy, hydroxy and halogen,
    and 1,3-dioxolan-2y is substituted by n radicals (C 1 -C 8 ) -alkyl,
    or R 6 by n radicals from the group halogen, (C 1 -C 6 ) alkyl, halogeno (C 1 -C 4 ) -acoxy and halogeno (C 1 -C 4 ) alkyl substituted heterocyclyl.
    m means 0 or 1, and
    n is 0, 1 or 2.
  • Particular preference is given to compounds of the general formula (I) in which
    R 2 is methyl,
    R 3 is methyl, ethyl, cyclopropyl or iso-propyl,
    or R 2 and R 3 together are (CH 2 ) 4 or (CH 2 ) 5 ,
    R 4 is methyl,
    R 5 is methyl or chlorine,
    A is a bond, -O-, -S-, -CH 2 -CH 2 -, -CH 2 -, -OCH 2 - or -CH = CH-, in particular a bond or -O-,
    R 6 means by n radicals from the group halogen, cyano, phenoxy, (C 1 -C 4 ) -alkylcarbonyl, (C 1 -C 4 ) -alkyl, (C 1 -C 6 ) -alkoxy, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl and 1,3-dioxolan-2yl substituted phenyl or naphthyl, where the radicals mentioned are (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy , (C 2 -C 6 ) -alkenyl and (C 2 -C 6 ) -alkynyl are substituted by n radicals from the group consisting of (C 1 -C 4 ) -alkoxy, hydroxy and halogen,
    and 1,3-dioxolan-2y is substituted by n radicals (C 1 -C 8 ) -alkyl,
    or R 6 by n radicals from the group halogen, (C 1 -C 6 ) alkyl, halogeno (C 1 -C 4 ) alkoxy and halogeno (C 1 -C 4 ) alkyl substituted pyridinyl, thiadiazolyl or thiazolyl,
    m means 1, and
    n is 0, 1 or 2.
  • The compounds of formula (I) are made EP 1 150 944 B1 known and are accessible by the production methods described therein.
  • The Compounds of formula (I) have an excellent herbicidal Efficiency against a broad spectrum economically more important monocotyledonous and dicotyledonous harmful plants. Also difficult to combat Perennial weeds made from rhizomes, rootstalks or other permanent organs are eliminated by the active ingredients well recorded. It is usually irrelevant whether the Substances applied in the pre-sowing, pre-emergence or post-emergence process become. In particular, some representatives of the mono- and dicotyledonous weed flora called by the compounds of Formula (I) can be controlled without having to the naming is a limitation to certain species should. On the side of monocotyledonous weed species, for. Avena, Lolium, Alopecurus, Phalaris, Echinochloa, Digitaria, Setaria as well Cyperus species from the annuelle group and on the part of the perennial Species Agropyron, Cynodon, Imperata as well as sorghum and perennial Cyperus species well detected.
  • In dicotyledonous weed species, the spectrum of activity extends to species such. Galium, Viola, Ve ronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Sida, Matricaria and Abutilon on the annull side, as well as Convolvulus, Cirsium, Rumex and Artemisia in perennial weeds. Under the specific culture conditions in rice occurring harmful plants such. B. Echinochloa, Sagittaria, Alisma, Eleocharis, Scirpus and Cyperus are also combated by the compounds of formula (I) also excellent. When the compounds of formula (I) are applied to the surface of the earth prior to germination, either weed seedling emergence is completely prevented or the weeds grow to the cotyledon stage but then cease to grow and eventually die after three to four weeks completely off. Upon application of the active ingredients to the green parts of the plants postemergence also occurs very quickly after treatment, a drastic halt in growth and the weed plants remain in the existing stage of application growth stage or die after a certain time completely, so that in this way one for the crops harmful weed competition is eliminated very early and sustainably. In particular, the compounds of formula (I) show excellent activity against Apera spica venti, Chenopodium album, Lamium purpureum, Polygonum convulvulus, Stellaria media, Veronica hederifolia, Veronica persica, Viola tricolor as well as against species of Amaranthus, Galium and Kochia.
  • Although the compounds of formula (I) have excellent herbicidal activity have mono- and dicotyledonous weeds, are crops economically significant crops such. Wheat, barley, rye, rice, corn, sugarbeet, cotton and soybean only marginally or not at all damaged. In particular, they have excellent compatibility in corn, rice, cereals and soybean. These compounds are suitable is therefore very good for the selective control of undesirable Plant growth in agricultural crops or ornamental plantings.
  • by virtue of their herbicidal properties, these compounds also for controlling harmful plants in cultures of known or to be developed genetically modified plants become. The transgenic plants are usually characterized special advantageous properties, for example, by resistances against certain pesticides, especially certain herbicides, Resistances to plant diseases or pathogens of plant diseases such as certain insects or microorganisms like mushrooms, bacteria or viruses. Other special properties concern z. B. the crop in terms of quantity, quality, Shelf life, composition and special ingredients. So are transgenic plants with increased starch content or altered quality of strength or those with other fatty acid composition of the crop known.
  • Prefers is the use of the compounds of formula (I) or their salts in economically important transgenic crops of useful and Ornamental plants, z. As cereals such as wheat, barley, rye, oats, Millet, rice, manioc and maize as well as in crops of sugar beet, Cotton, soybean, rapeseed, potato, tomato, pea and others Vegetables. Preferably, the compounds of formula (I) used as herbicides in crops which are against the phytotoxic effects of the herbicides are resistant or genetically resistant, especially soybean and corn.
  • Conventional ways of producing new plants which have modified properties in comparison to previously occurring plants consist, for example, in classical breeding methods and the production of mutants. Alternatively, new plants with altered properties can be generated by means of genetic engineering methods (see, for example, US Pat. EP-A-0221044 . EP-A-0131624 , For example, several cases have been described
    • - genetic modification of crops to modify the starch synthesized in the plants (eg. WO 92/11376 . WO 92/14827 . WO 91/19806 )
    • Transgenic crops which are resistant to certain glufosinate-type herbicides (eg. EP-A 0 242 236 . EP-A 0 242 246 ) or glyphosate ( WO 92/00377 ) or the sulfonylureas ( EP-A-0257993 . US-A-5013659 ) are resistant,
    • Transgenic crops, such as cotton, capable of producing Bacillus thuringiensis toxins (Bt toxins) which render plants resistant to certain pests ( EP-A 0 142 924 . EP-A 0 193 259 ).
    • Transgenic crops with modified fatty acid composition ( WO 91/13972 ).
  • Numerous molecular biological techniques that can be used to produce new transgenic plants with altered properties are known in principle; see, for. B. 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 or Christou, "Trends in Plant Science" 1 (1996) 423-431 ). For such genetic manipulations, nucleic acid molecules can be introduced into plasmids that have a mutagenesis or a sequence change by recombination of DNA Se allow frequencies. With the aid of the abovementioned standard methods, z. For example, base substitutions are made, partial sequences are removed, or natural or synthetic sequences are added. For the connection of the DNA fragments with one another adapters or linkers can be attached to the fragments.
  • The Production of plant cells with reduced activity a gene product can be, for. B. can be achieved by the expression at least one corresponding antisense RNA, a sense RNA for Obtaining a Cosuppressionseffektes or expression at least a suitably engineered ribozyme that specifically transcripts of the above gene product cleaves.
  • For this On the one hand, DNA molecules can be used including the entire coding sequence of a gene product possibly existing flanking sequences, as well DNA molecules that comprise only parts of the coding sequence, These parts need to be long enough to be in the cells to cause an antisense effect. It is also possible Use of DNA sequences that have a high degree of homology but not to the coding sequences of a gene product are completely identical.
  • In the expression of nucleic acid molecules in plants, the synthesized protein may be located in any compartment of the plant cell. But to achieve the localization in a particular compartment, z. For example, the coding region can be linked to DNA sequences that ensure localization in a particular compartment. Such sequences are known to the person skilled in the art (see, for example Braun et al., EMBO J. 11 (1992), 3219-3227 ; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850 ; Sonnewald et al., Plant J. 1 (1991), 95-106 ).
  • The Transgenic plant cells can be prepared by known techniques be regenerated to whole plants. In the transgenic plants they can in principle be plants of any plant species, d. H. both monocotyledonous and dicotyledonous plants. So are transgenic Plants available that have altered properties by over-expression, suppression or inhibition homologous (= natural) genes or gene sequences or expression heterologous (= foreign) genes or gene sequences.
  • at the use of the compounds of the formula (I) in transgenic cultures occur in addition to the effects observed in other cultures often has effects on harmful plants for the application is specific in the respective transgenic culture, for example, a modified or specially extended Weed spectrum that can be controlled changed Application rates used for the application can, preferably good compatibility with the herbicides, against which the transgenic culture is resistant, as well as Influence on growth and yield of transgenic crops. The invention therefore also relates to the use of the compounds of the formula (I) as herbicides for controlling harmful plants in transgenic crops.
  • Furthermore the compounds of the formula (I) have excellent growth-regulatory Properties on crops. They regulate in the plant 's own metabolism and can thus targeted influencing of phytonutrients and harvest relief such as B. by triggering desiccation and stunted growth be used. Furthermore, they are also suitable for general Control and inhibition of unwanted vegetative growth, without killing the plants. An inhibition of the vegetative Growth plays an important role in many mono- and dicotyledonous cultures, as the storage thereby reduced or completely prevented can be.
  • The compounds of the formula (I) can be formulated in various ways into herbicidal agents, depending on which biological and / or chemical-physical parameters are predetermined. As formulation options come z. B. in question: 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, dusts (DP), capsule suspensions (CS), 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. These individual types of formulation are known in principle and are described, for example, in: Winnacker-Kuchler, "Chemical Technology", Volume 7, C. Hauser Verlag Munich, 4th ed. 1986 . Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, NY, 1973 ; K. Martens, "Spray Drying" Handbook, 3rd ed. 1979, G. Goodwin Ltd. London , Such herbicidal compositions are also the subject of the invention.
  • The necessary formulation auxiliaries, such as inert materials, surfactants, solvents and other additives are likewise known and are described, for example, in: Watkins, "Handbook of Insecticides Dust Diluents and Carriers", 2nd ed., Darland Books, Caldwell NJ, H. v. Chr. Olphen, "Introduction to Clay Colloid Chemistry"; 2nd 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, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964 ; Schönfeldt, "Grenzflächenaktive Äthylenoxidaddukte", Wiss. Publishing company, Stuttgart 1976 ; Winnacker-Kuchler, "Chemical Technology", Volume 7, C. Hauser Verlag Munich, 4th ed. 1986 ,
  • wettable powder are preparations which are evenly dispersible in water, besides the active substance except a dilution or inert or surfactants of ionic and / or nonionic nature (Wetting agent, dispersant), z. For example, polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, Alkanesulfonates, alkylbenzenesulfonates, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, lignosulfonate sodium, dibutylnaphthalene-sulphonate sodium or also contain oleoylmethyltaurine acid sodium. For the production the spray powder, the herbicidal active ingredients, for example in conventional apparatus such as hammer mills, blower mills and air-jet mills finely ground and simultaneously or then mixed with the formulation auxiliaries.
  • emulsifiable Concentrates are made by dissolving the active ingredient in one organic solvents z. B. butanol, cyclohexanone, DMF, xylene or higher-boiling aromatics or hydrocarbons or Mixtures of these solvents with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers) produced. As emulsifiers z. B. can be used: Alkylarylsulfonic acid calcium salts such as calcium dodecylbenzene sulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, Alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, Alkyl polyether, sorbitan esters such. B. sorbitan fatty acid esters or Polyoxethylenensorbitanester such. B. polyoxyethylene sorbitan fatty acid esters.
  • dusts obtained by grinding the active ingredient with finely divided solid substances, eg. Talc, natural clays such as kaolin, Bentonite and pyrophyllite, or diatomaceous earth. Suspension concentrates can be based on water or oil. You can, for example by wet grinding by means of commercially available bead mills and optionally addition of surfactants, as described for. B. above at the other Formulation types already listed are produced become.
  • emulsions z. As oil-in-water emulsions (EW), can be, for example by means of stirrers, colloid mills and / or static Mixers using aqueous organic Solvents and optionally surfactants, as z. B. already listed above for the other formulation types are, manufacture.
  • granules can either by dehydrating the drug made on adsorptive, granulated inert material or by applying active substance concentrates by means of adhesives, z. As polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the surface of carriers such as sand, Kaolinite or granulated inert material. Also can suitable active ingredients in the usual for the production of fertilizer granules Were - if desired, mixed with fertilizers - granulated. Water-dispersible granules are usually according to the usual Methods such as spray drying, fluidized bed granulation, Plate granulation, mixing with high-speed mixers and Extrusion made without solid inert material.
  • For the preparation of plate, fluidized bed, extruder and spray granules see, for. B. Method in "Spray-Drying Handbook" 3rd Ed. 1979, G. Goodwin Ltd., London ; JE Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 ff ; "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Rill, New York 1973, pp. 8-57 , For more details on pesticide formulation see, e.g. B. GC Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pp. 81-96 and JD Freyer, SA Evans, "Weed Control Handbook", 5th ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103 ,
  • The agrochemical preparations generally contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of active compound of the formula (I). In wettable powders, the active ingredient concentration z. B. about 10 to 90 wt .-%, the remainder to 100 wt .-% consists of conventional formulation components. For emulsifiable concentrates, the active ingredient concentration may be about 1 to 90, preferably 5 to 80 wt .-%. Dusty formulations contain from 1 to 30% by weight of active ingredient, preferably usually from 5 to 20% by weight of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt .-% of active ingredient. In the case of water-dispersible granules, the active ingredient content depends, in part, on whether the active compound is liquid or solid and which granulating aids, fillers, etc. are used. In the case of the water-dispersible granules, the content of active ingredient is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
  • Besides If necessary, the active substance formulations mentioned contain the customary adhesion, wetting, dispersing, emulsifying, Penetration, preservative, antifreeze and solvent, Fillers, carriers and dyes, defoamers, Evaporation inhibitor and the pH and the viscosity affecting Medium.
  • On The basis of these formulations can also be combined with other pesticide-active substances such. As insecticides, acaricides, Herbicides, fungicides, as well as with safeners, fertilizers and / or growth regulators produce, for. B. in the form of a finished formulation or as a tank mix.
  • As a combination partner for the compounds of formula (I) in mixture formulations or in the tank mix, for example, known active ingredients can be used, as described, for. In Weed Research 26, 441-445 (1986) or The Pesticide Manual, 13th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2003 and cited there literature are described. As known herbicides, which can be combined with the compounds of formula (I), z. The following compounds are to be mentioned (note: the compounds are denoted either by the "common name" according to the International Organization for Standardization (ISO) or by the chemical name, if appropriate together with a customary code number):
    acetochlor; acifluorfen; aclonifen; AKH 7088, ie methyl [[[1- [5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrophenyl] -2-methoxyethylidene] amino] oxy] acetic acid and acetic acid; alachlor; alloxydim; ametryn; amicarbazone; amidosulfuron; amitrol; AMS, ie ammonium sulfamate; anilofos; asulam; atrazine; azimsulfurones (DPX-A8947); aziprotryn; barban; BAS 516H, ie 5-fluoro-2-phenyl-4H-3,1-benzoxazin-4-one; benazolin; benfluralin; benfuresate; bensulfuron-methyl; bensulide; bentazone; benzofenap; benzofluor; benzoylprop-ethyl; benzthiazuron; bialaphos; bifenox; bromacil; bromobutide; bromofenoxim; bromoxynil; bromuron; buminafos; busoxinone; butachlor; butamifos; butenachlor; buthidazole; butraline; butylate; cafenstrole (CH-900); carbetamide; cafentrazone (ICI-A0051); CDAA, ie 2-chloro-N, N-di-2-propenylacetamide; CDEC, ie diethyldithiocarbamic acid 2-chloroallyl ester; chlomethoxyfen; chloramben; chloroazifop-butyl, chlorormesulone (ICI-A0051); chlorbromuron; chlorbufam; chlorfenac; chlorflurecol-methyl; chloridazon; chlorimuron ethyl; chlornitrofen; chlorotoluron; chloroxuron; chlorpropham; chlorsulfuron; chlorthal-dimethyl; chlorthiamid; cinmethylin; cinosulfuron; clethodim; clodinafop and its ester derivatives (eg clodinafop-propargyl); clomazone; clomeprop; cloproxydim; clopyralid; cumyluron (JC 940); cyanazine; cycloate; Cyclosulfamuron (AC 104); cycloxydim; cycluron; cyhalofop and its ester derivatives (eg, butyl ester, DEH-112); cyperquat; cyprazine; cyprazole; daimuron; 2,4-DB; dalapon; desmedipham; Desmetryn; di-allate; dicamba; dichlobenil; dichloroprop; diclofop and its esters such as diclofop-methyl; diethatyl; difenoxuron; difenzoquat; diflufenican; dimefuron; dimethachlor; dimethametryn; dimethenamid (SAN-582H); dimethazone, clomazone; dimethipin; dimetrasulfuron, dinitramine; dinoseb; dinoterb; diphenamid; dipropetryn; diquat; dithiopyr; diuron; DNOC; eglinazine-ethyl; EL 77, ie 5-cyano-1- (1,1-dimethylethyl) -N-methyl-1H-pyrazole-4-carboxamide; endothal; EPTC; esprocarb; ethalfluralin; ethametsulfuron-methyl; Ethidimuron; ethiozin; ethofumesate; F5231, ie N- [2-chloro-4-fluoro-5- [4- (3-fluoropropyl) -4,5-dihydro-5-oxo-1H-tetrazol-1-yl] -phenyl] -ethanesulfonamide; ethoxyfen and its esters (eg ethyl ester, HN-252); etobenzanide (HW 52); fenoprop; fenoxan, fenoxaprop and fenoxaprop-P and their esters, eg. Fenoxaprop-P-ethyl and fenoxaprop-ethyl; fenoxydim; fenuron; flamprop-methyl; flazasulfuron; fluazifop and fluazifop-P and their esters, e.g. Fluazifop-butyl and fluazifop-p-butyl; fluchloralin; flumetsulam; flumeturon; flumiclorac and its esters (eg, pentyl ester, S-23031); flumioxazine (S-482); flumipropyn; flupoxam (KNW-739); fluorodifen; fluoroglycofen-ethyl; flupropacil (UBIC-4243); fluridone; flurochloridone; fluroxypyr; flurtamone; fomesafen; fosamine; furyloxyfen; glufosinate; glyphosate; halo safen; halosulfuron and its esters (eg, methyl ester, NC-319); haloxyfop and its esters; haloxyfop-P (= R-haloxyfop) and its esters; hexazinone; imazapyr; imazamethabenz-methyl; imazaquin and salts such as the ammonium salt; ioxynil; imazethamethapyr; imazethapyr; imazosulfuron; isocarbamid; isopropalin; isoproturon; isouron; isoxaben; isoxapyrifop; karbutilate; lactofen; lenacil; linuron; MCPA; MCPB; mecoprop; mefenacet; mefluidide; metamitron; metazachlor; metham; methabenzthiazuron; methazole; methoxyphenone; methyldymron; metabenzuron, methobenzuron; metobromuron; metolachlor; metosulam (XRD 511); metoxuron; metribuzin; metsulfuron-methyl; MH; molinate; monalide; monolinuron; monuron; monocarbamide dihydrogen sulfates; MT 128, ie 6-chloro-N- (3-chloro-2-propenyl) -5-methyl-N-phenyl-3-pyridazineamine; MT 5950, ie N- [3-chloro-4- (1-methylethyl) phenyl] -2-methylpentanamide; naproanilide; napropamide; naptalam; NC 310, ie 4- (2,4-dichlorobenzoyl) -1-methyl-5-benzyloxypyrazole; neburon; nicosulfuron; nipyraclophen; nitralin; nitrofen; nitrofluorfen; norflurazon; orbencarb; oryzalin; oxadiargyl (RP-020630); oxadiazon; oxyfluorfen; paraquat; pebulate; pendimethalin; perfluidone; phenisopham; phenmedipham; picloram; pinoxaden; piperophos; piributicarb; pirifenop-butyl; pretilachlor; primisulfuron-methyl; procyazine; prodi amines; profiuralin; proglinazine-ethyl; prometon; prometryne; propachlor; propanil; propaquizafop and its esters; propazine; propham; propisochlor; propoxycarbazone; Propyzamide; prosulfalin; prosulfocarb; prosulfuron (CGA-152005); prynachlor; pyraclonil, pyrazolinates; pyrazon; pyrazosulfuron-ethyl; pyrazoxyfen; pyridate; pyrithiobac (KIH-2031); pyroxofop and its esters (eg propargyl esters); quinclorac; quinmerac; quinofop and its ester derivatives, quizalofop and quizaiofop-P and their ester derivatives z. Eg quizalofop-ethyl; quizaiofop-P-tefuryl and -ethyl; renriduron; rimsulfuron (DPX-E 9636); S 275, ie 2- [4-chloro-2-fluoro-5- (2-propynyloxy) -phenyl] -4,5,6,7-tetrahydro-2H-indazole; secbumeton; sethoxydim; siduron; simazine; simetryn; SN 106279, ie 2 - [[7- [2-chloro-4- (trifluoromethyl) phenoxy] -2-naphthalenyl] oxy] propanoic acid and methyl ester; sulfentrazone (FMC-97285, F-6285); sulfazuron; sulfometuron-methyl; sulfosate (ICI-A0224); TCA; tebutam (GCP-5544); tebuthiuron; terbacil; terbucarb; terbuchlor; terbumeton; Terbuthylazine; terbutryn; TFH 450, ie, N, N-diethyl-3 - [(2-ethyl-6-methylphenyl) sulfonyl] -1H-1,2,4-triazole-1-carboxamide; thenylchlor (NSK-850); thiazafluron; thiazopyr (Mon-13200); thidiazimin (SN-24085); thiobencarb; thifensulfuron-methyl; tiocarbazil; tralkoxydim; tri-allate; triasulfuron; triazofenamide; tribenuron-methyl; triciopyr; tridiphane; trietazine; trifluralin; triflusulfuron and esters (eg, methyl ester, DPX-66037); trimeturon; tsitodef; vernolate; WL 110547, ie 5-phenoxy-1- [3- (trifluoromethyl) -phenyl] -1H-tetrazole; UBH-509; D-489; LS 82-556; KPP-300; NC-324; NC-330; KH-218; DPX-N8189; SC-0774; Dowco-535; DK-8910; V-53482; PP-600; MBH-001; KIH-9201; ET-751; KIH-6127; KIH-2023 and KIH-485.
  • to Application will be in commercial form If appropriate, formulations are diluted in the customary manner z. As in wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules by means of water. Powdery Preparations, ground or spreading granules and sprayable Solutions become common before application no longer diluted with other inert substances. With the outside Conditions such as temperature, humidity, the type of used Herbicides, u. a. varies the required application rate of compounds of the formula (I). It can vary within wide limits, eg. B. between 0.001 and 1.0 kg / ha or more active substance, preferably However, it is between 5 and 750 g / ha, especially between 5 and 250 g / ha.
  • The The following examples illustrate the invention.
  • The Abbreviations used here mean:
  • iPr
    = iso-propyl
    et
    = Ethyl
    Bu
    = tertiary-butyl
    cPr
    = cyclopropyl
    me
    = Methyl
    pr
    = Propyl
    Ph
    = Phenyl
      table 1: Compounds of the invention of the general Formula (I) in which R4 for methyl stands.
    Figure 00180001
      No. R 2 R 3 R 5 A R 6 1 me me me 0 3-Br-5-F-phenyl 2 me et me O 3-Br-5-F-phenyl 3 (CH 2 ) 4 me O 3-Br-5-F-phenyl 4 (CH 2 ) 5 me O 3-Br-5-F-phenyl 5 me me me S 3-Br-5-F-phenyl 6 me et me S 3-Br-5-F-phenyl 7 (CH 2 ) 4 me S 3-Br-5-F-phenyl 8th (CH 2 ) 5 me S 3-Br-5-F-phenyl 9 me me me CH 2 CH 2 3-Br-5-F-phenyl 10 me et me CH 2 CH 2 3-Br-5-F-phenyl 11 (CH 2 ) 4 me CH 2 CH 2 3-Br-5-F-phenyl 12 (CH 2 ) 5 me CH 2 CH 2 3-Br-5-F-phenyl 13 me me me CH 2 = CH 2 3-Br-5-F-phenyl 14 me et me CH 2 = CH 2 3-Br-5-F-phenyl 15 (CH 2 ) 4 me CH 2 = CH 2 3-Br-5-F-phenyl 16 (CH 2 ) 5 me CH 2 = CH 2 3-Br-5-F-phenyl 17 me me me O 4-Br-3-iPr-phenyl 18 me et me O 4-Br-3-iPr-phenyl 19 (CH 2 ) 4 me O 4-Br-3-iPr-phenyl 20 (CH 2 ) 5 me O 4-Br-3-iPr-phenyl 21 me me me S 4-Br-3-iPr-phenyl 22 me et me S 4-Br-3-iPr-phenyl 23 (CH 2 ) 4 me S 4-Br-3-iPr-phenyl 24 (CH 2 ) 5 me S 4-Br-3-iPr-phenyl 25 me me me CH 2 CH 2 4-Br-3-iPr-phenyl 26 me et me CH 2 CH 2 4-Br-3-iPr-phenyl 27 (CH 2 ) 4 me CH 2 CH 2 4-Br-3-iPr-phenyl 28 (CH 2 ) 5 me CH 2 CH 2 4-Br-3-iPr-phenyl 29 me me me CH 2 = CH 2 4-Br-3-iPr-phenyl 30 me et me CH 2 = CH 2 4-Br-3-iPr-phenyl 31 (CH 2 ) 4 me CH 2 = CH 2 4-Br-3-iPr-phenyl 32 (CH 2 ) 5 me CH 2 = CH 2 4-Br-3-iPr-phenyl 33 me me me O 4-Cl-3-CF 3 -phenyl 34 me et me O 4-Cl-3-CF 3 -phenyl 35 (CH 2 ) 4 me O 4-Cl-3-CF 3 -phenyl 36 (CH 2 ) 5 me O 4-Cl-3-CF 3 -phenyl 37 me me me S 4-Cl-3-CF 3 -phenyl 38 me et me S 4-Cl-3-CF 3 -phenyl 39 (CH 2 ) 4 me S 4-Cl-3-CF 3 -phenyl 40 (CH 2 ) 5 me S 4-Cl-3-CF 3 -phenyl 41 me me me CH 2 CH 2 4-Cl-3-CF 3 -phenyl 42 me et me CH 2 CH 2 4-Cl-3-CF 3 -phenyl 43 (CH 2 ) 4 me CH 2 CH 2 4-Cl-3-CF 3 -phenyl 44 (CH 2 ) 5 me CH 2 CH 2 4-Cl-3-CF 3 -phenyl 45 me me me CH 2 = CH 2 4-Cl-3-CF 3 -phenyl 46 me et me CH 2 = CH 2 4-Cl-3-CF 3 -phenyl 47 (CH 2 ) 4 me CH 2 = CH 2 4-Cl-3-CF 3 -phenyl 48 (CH 2 ) 5 me CH 2 = CH 2 4-Cl-3-CF 3 -phenyl 49 me me me O 4-Cl-3-tBu-phenyl 50 me et me O 4-Cl-3-tBu-phenyl 51 (CH 2 ) 4 me O 4-Cl-3-tBu-phenyl 52 (CH 2 ) 4 me O 4-Cl-3-tBu-phenyl 53 me me me S 4-Cl-3-tBu-phenyl 54 me et me S 4-Cl-3-tBu-phenyl 55 (CH 2 ) 4 me S 4-Cl-3-tBu-phenyl 56 (CH 2 ) 5 me S 4-Cl-3-tBu-phenyl 57 me me me CH 2 CH 2 4-Cl-3-tBu-phenyl 58 me et me CH 2 CH 2 4-Cl-3-tBu-phenyl 59 (CH 2 ) 4 me CH 2 CH 2 4-Cl-3-tBu-phenyl 60 (CH 2 ) 5 me CH 2 CH 2 4-Cl-3-tBu-phenyl 61 me me me CH 2 = CH 2 4-Cl-3-tBu-phenyl 62 me et me CH 2 = CH 2 4-Cl-3-tBu-phenyl 63 (CH 2 ) 4 me CH 2 = CH 2 4-Cl-3-tBu-phenyl 64 (CH 2 ) 5 me CH 2 = CH 2 4-Cl-3-tBu-phenyl 65 me me me O 4-Cl-2-Me-Phenyl 66 me et me O 4-Cl-2-Me-Phenyl 67 (CH 2 ) 4 me O 4-Cl-2-Me-Phenyl 68 (CH 2 ) 5 me O 4-Cl-2-Me-Phenyl 69 me me me S 4-Cl-2-Me-Phenyl 70 me et me S 4-Cl-2-Me-Phenyl 71 (CH 2 ) 4 me S 4-Cl-2-Me-Phenyl 72 (CH 2 ) 5 me S 4-Cl-2-Me-Phenyl 73 me me me CH 2 CH 2 4-Cl-2-Me-Phenyl 74 me et me CH 2 CH 2 4-Cl-2-Me-Phenyl 75 (CH 2 ) 4 me CH 2 CH 2 4-Cl-2-Me-Phenyl 76 (CH 2 ) 5 me CH 2 CH 2 4-Cl-2-Me-Phenyl 77 me me me CH 2 = CH 2 4-Cl-2-Me-Phenyl 78 me et me CH 2 = CH 2 4-Cl-2-Me-Phenyl 79 (CH 2 ) 4 me CH 2 = CH 2 4-Cl-2-Me-Phenyl 80 (CH 2 ) 5 me CH 2 = CH 2 4-Cl-2-Me-Phenyl 81 me me me O 4-Cl-3-Me-Phenyl 82 me et me O 4-Cl-3-Me-Phenyl 83 (CH 2 ) 4 me O 4-Cl-3-Me-Phenyl 84 (CH 2 ) 5 me O 4-Cl-3-Me-Phenyl 85 me me me S 4-Cl-3-Me-Phenyl 86 me et me S 4-Cl-3-Me-Phenyl 87 (CH 2 ) 4 me S 4-Cl-3-Me-Phenyl 88 (CH 2 ) 5 me S 4-Cl-3-Me-Phenyl 89 me me me CH 2 CH 2 4-Cl-3-Me-Phenyl 90 me et me CH 2 CH 2 4-Cl-3-Me-Phenyl 91 (CH 2 ) 4 me CH 2 CH 2 4-Cl-3-Me-Phenyl 92 (CH 2 ) 5 me CH 2 CH 2 4-Cl-3-Me-Phenyl 93 me me me CH 2 = CH 2 4-Cl-3-Me-Phenyl 94 me et me CH 2 = CH 2 4-Cl-3-Me-Phenyl 95 (CH 2 ) 4 me CH 2 = CH 2 4-Cl-3-Me-Phenyl 96 (CH 2 ) 5 me CH 2 = CH 2 4-Cl-3-Me-Phenyl 97 me me me O 4-Cl-3-iPr-phenyl 98 me et me O 4-Cl-3-iPr-phenyl 99 (CH 2 ) 4 me O 4-Cl-3-iPr-phenyl 100 (CH 2 ) 5 me O 4-Cl-3-iPr-phenyl 101 me me me S 4-Cl-3-iPr-phenyl 102 me et me S 4-Cl-3-iPr-phenyl 103 (CH 2 ) 4 me S 4-Cl-3-iPr-phenyl 104 (CH 2 ) 5 me S 4-Cl-3-iPr-phenyl 105 me me me CH 2 CH 2 4-Cl-3-iPr-phenyl 106 me et me CH 2 CH 2 4-Cl-3-iPr-phenyl 107 (CH 2 ) 4 me CH 2 CH 2 4-Cl-3-iPr-phenyl 108 (CH 2 ) 5 me CH 2 CH 2 4-Cl-3-iPr-phenyl 109 me me me CH 2 = CH 2 4-Cl-3-iPr-phenyl 110 me et me CH 2 = CH 2 4-Cl-3-iPr-phenyl 111 (CH 2 ) 4 me CH 2 = CH 2 4-Cl-3-iPr-phenyl 112 (CH 2 ) 5 me CH 2 = CH 2 4-Cl-3-iPr-phenyl 113 me me me O 4-Cl-6-iPr-pyridin-2-yl 114 me et me O 4-Cl-6-iPr-pyridin-2-yl 115 (CH 2 ) 4 me O 4-Cl-6-iPr-pyridin-2-yl 116 (CH 2 ) 5 me O 4-Cl-6-iPr-pyridin-2-yl 117 me me me S 4-Cl-6-iPr-pyridin-2-yl 118 me et me S 4-Cl-6-iPr-pyridin-2-yl 119 (CH 2 ) 4 me S 4-Cl-6-iPr-pyridin-2-yl 120 (CH 2 ) 5 me S 4-Cl-6-iPr-pyridin-2-yl 121 me me me OCH 2 4-Cl-6-iPr-pyridin-2-yl 122 me et me OCH 2 4-Cl-6-iPr-pyridin-2-yl 123 (CH 2 ) 4 me OCH 2 4-Cl-6-iPr-pyridin-2-yl 124 (CH 2 ) 5 me OCH 2 4-Cl-6-iPr-pyridin-2-yl 125 me me me CH 2 = CH 2 4-Cl-6-iPr-pyridin-2-yl 126 me et me CH 2 = CH 2 4-Cl-6-iPr-pyridin-2-yl 127 (CH 2 ) 4 me CH 2 = CH 2 4-Cl-6-iPr-pyridin-2-yl 128 (CH 2 ) 5 me CH 2 = CH 2 4-Cl-6-iPr-pyridin-2-yl 129 me me me O 3- (2-Cl-pyridin-3-yl) -phenyl 130 me et me O 3- (2-Cl-pyridin-3-yl) -phenyl 131 (CH 2 ) 4 me O 3- (2-Cl-pyridin-3-yl) -phenyl 132 (CH 2 ) 5 me O 3- (2-Cl-pyridin-3-yl) -phenyl 133 me me me S 3- (2-Cl-pyridin-3-yl) -phenyl 134 me et me S 3- (2-Cl-pyridin-3-yl) -phenyl 135 (CH 2 ) 4 me S 3- (2-Cl-pyridin-3-yl) -phenyl 136 (CH 2 ) 5 me S 3- (2-Cl-pyridin-3-yl) -phenyl 137 me me me OCH 2 2-Cl-pyridin-3-yl 138 me et me OCH 2 2-Cl-pyridin-3-yl 139 (CH 2 ) 4 me OCH 2 2-Cl-pyridin-3-yl 140 (CH 2 ) 5 me OCH 2 2-Cl-pyridin-3-yl 141 me me me CH 2 = CH 2 2-Cl-pyridin-3-yl 142 me et me CH 2 = CH 2 2-Cl-pyridin-3-yl 143 (CH 2 ) 4 me CH 2 = CH 2 2-Cl-pyridin-3-yl 144 (CH 2 ) 5 me CH 2 = CH 2 2-Cl-pyridin-3-yl 145 me me me O 3-CF 3 -4-Me-phenyl 146 me et me O 3-CF 3 -4-Me-phenyl 147 (CH 2 ) 4 me O 3-CF 3 -4-Me-phenyl 148 (CH 2 ) 5 me O 3-CF 3 -4-Me-phenyl 149 me me me S 3-CF 3 -4-Me-phenyl 150 me et me S 3-CF 3 -4-Me-phenyl 151 (CH 2 ) 4 me S 3-CF 3 -4-Me-phenyl 152 (CH 2 ) 5 me S 3-CF 3 -4-Me-phenyl 153 me me me CH 2 CH 2 3-CF 3 -4-Me-phenyl 154 me et me CH 2 CH 2 3-CF 3 -4-Me-phenyl 155 (CH 2 ) 4 me CH 2 CH 2 3-CF 3 -4-Me-phenyl 156 (CH 2 ) 5 me CH 2 CH 2 3-CF 3 -4-Me-phenyl 157 me me me CH 2 = CH 2 3-CF 3 -4-Me-phenyl 158 me et me CH 2 = CH 2 3-CF 3 -4-Me-phenyl 159 (CH 2 ) 4 me CH 2 = CH 2 3-CF 3 -4-Me-phenyl 160 (CH 2 ) 5 me CH 2 = CH 2 3-CF 3 -4-Me-phenyl 161 me me me O 4-F-3-OCF 3 -phenyl 162 me et me O 4-F-3-OCF 3 -phenyl 163 (CH 2 ) 4 me O 4-F-3-OCF 3 -phenyl 164 (CH 2 ) 5 me O 4-F-3-OCF 3 -phenyl 165 me me me S 4-F-3-OCF 3 -phenyl 166 me et me S 4-F-3-OCF 3 -phenyl 167 (CH 2 ) 4 me S 4-F-3-OCF 3 -phenyl 168 (CH 2 ) 5 me S 4-F-3-OCF 3 -phenyl 169 me me me CH 2 CH 2 4-F-3-OCF 3 -phenyl 170 me et me CH 2 CH 2 4-F-3-OCF 3 -phenyl 171 (CH 2 ) 4 me CH 2 CH 2 4-F-3-OCF 3 -phenyl 172 (CH 2 ) 5 me CH 2 CH 2 4-F-3-OCF 3 -phenyl 173 me me me CH 2 = CH 2 4-F-3-OCF 3 -phenyl 174 me et me CH 2 = CH 2 4-F-3-OCF 3 -phenyl 175 (CH 2 ) 4 me CH 2 = CH 2 4-F-3-OCF 3 -phenyl 176 (CH 2 ) 5 me CH 2 = CH 2 4-F-3-OCF 3 -phenyl 177 me me me O 3-I-5-CF 3 -phenyl 178 me et me O 3-I-5-CF 3 -phenyl 179 (CH 2 ) 4 me O 3-I-5-CF 3 -phenyl 180 (CH 2 ) 5 me O 3-I-5-CF 3 -phenyl 181 me me me S 3-I-5-CF 3 -phenyl 182 me et me S 3-I-5-CF 3 -phenyl 183 (CH 2 ) 4 me S 3-I-5-CF 3 -phenyl 184 (CH 2 ) 5 me S 3-I-5-CF 3 -phenyl 185 me me me CH 2 CH 2 3-I-5-CF 3 -phenyl 186 me et me CH 2 CH 2 3-I-5-CF 3 -phenyl 187 (CH 2 ) 4 me CH 2 CH 2 3-I-5-CF 3 -phenyl 188 (CH 2 ) 5 me CH 2 CH 2 3-I-5-CF 3 -phenyl 189 me me me CH 2 = CH 2 3-I-5-CF 3 -phenyl 190 me et me CH 2 = CH 2 3-I-5-CF 3 -phenyl 191 (CH 2 ) 4 me CH 2 = CH 2 3-I-5-CF 3 -phenyl 192 (CH 2 ) 5 me CH 2 = CH 2 3-I-5-CF 3 -phenyl 193 me me me O 3-tBu-phenyl 194 me et me O 3-tBu-phenyl 195 (CH 2 ) 4 me O 3-tBu-phenyl 196 (CH 2 ) 5 me O 3-tBu-phenyl 197 me me me S 3-tBu-phenyl 198 me et me S 3-tBu-phenyl 199 (CH 2 ) 4 me S 3-tBu-phenyl 200 (CH 2 ) 5 me S 3-tBu-phenyl 201 me me me CH 2 CH 2 3-tBu-phenyl 202 me et me CH 2 CH 2 3-tBu-phenyl 203 (CH 2 ) 4 me CH 2 CH 2 3-tBu-phenyl 204 (CH 2 ) 5 me CH 2 CH 2 3-tBu-phenyl 205 me me me CH 2 = CH 2 3-tBu-phenyl 206 me et me CH 2 = CH 2 3-tBu-phenyl 207 (CH 2 ) 4 me CH 2 = CH 2 3-tBu-phenyl 208 (CH 2 ) 5 me CH 2 = CH 2 3-tBu-phenyl 209 me me me O 4-tBu-phenyl 210 me et me O 4-tBu-phenyl 211 (CH 2 ) 4 me O 4-tBu-phenyl 212 (CH 2 ) 5 me O 4-tBu-phenyl 213 me me me S 4-tBu-phenyl 214 me et me S 4-tBu-phenyl 215 (CH 2 ) 4 me S 4-tBu-phenyl 216 (CH 2 ) 5 me S 4-tBu-phenyl 217 me me me CH 2 CH 2 4-tBu-phenyl 218 me et me CH 2 CH 2 4-tBu-phenyl 219 (CH 2 ) 4 me CH 2 CH 2 4-tBu-phenyl 220 (CH 2 ) 5 me CH 2 CH 2 4-tBu-phenyl 221 me me me CH 2 = CH 2 4-tBu-phenyl 222 me et me CH 2 = CH 2 4-tBu-phenyl 223 (CH 2 ) 4 me CH 2 = CH 2 4-tBu-phenyl 224 (CH 2 ) 5 me CH 2 = CH 2 4-tBu-phenyl 225 me me me O 4-CN-3-CF 3 -phenyl 226 me et me O 4-CN-3-CF 3 -phenyl 227 (CH 2 ) 4 me O 4-CN-3-CF 3 -phenyl 228 (CH 2 ) 5 me O 4-CN-3-CF 3 -phenyl 229 me me me S 4-CN-3-CF 3 -phenyl 230 me et me S 4-CN-3-CF 3 -phenyl 231 (CH 2 ) 4 me S 4-CN-3-CF 3 -phenyl 232 (CH 2 ) 5 me S 4-CN-3-CF 3 -phenyl 233 me me me CH 2 CH 2 4-CN-3-CF 3 -phenyl 234 me et me CH 2 CH 2 4-CN-3-CF 3 -phenyl 235 (CH 2 ) 4 me CH 2 CH 2 4-CN-3-CF 3 -phenyl 236 (CH 2 ) 5 me CH 2 CH 2 4-CN-3-CF 3 -phenyl 237 me me me CH 2 = CH 2 4-CN-3-CF 3 -phenyl 238 me et me CH 2 = CH 2 4-CN-3-CF 3 -phenyl 239 (CH 2 ) 4 me CH 2 = CH 2 4-CN-3-CF 3 -phenyl 240 (CH 2 ) 5 me CH 2 = CH 2 4-CN-3-CF 3 -phenyl 241 me me me O 4-CF 3 -phenyl 242 me et me O 4-CF 3 -phenyl 243 (CH 2 ) 4 me O 4-CF 3 -phenyl 244 (CH 2 ) 5 me O 4-CF 3 -phenyl 245 me me me S 4-CF 3 -phenyl 246 me et me S 4-CF 3 -phenyl 247 (CH 2 ) 4 me S 4-CF 3 -phenyl 248 (CH 2 ) 5 me S 4-CF 3 -phenyl 249 me me me CH 2 CH 2 4-CF 3 -phenyl 250 me et me CH 2 CH 2 4-CF 3 -phenyl 251 (CH 2 ) 4 me CH 2 CH 2 4-CF 3 -phenyl 252 (CH 2 ) 5 me CH 2 CH 2 4-CF 3 -phenyl 253 me me me CH 2 = CH 2 4-CF 3 -phenyl 254 me et me CH 2 = CH 2 4-CF 3 -phenyl 255 (CH 2 ) 4 me CH 2 = CH 2 4-CF 3 -phenyl 256 (CH 2 ) 5 me CH 2 = CH 2 4-CF 3 -phenyl 257 me me me O 2-Me-Phenyl 258 me et me O 2-Me-Phenyl 259 (CH 2 ) 4 me O 2-Me-Phenyl 260 (CH 2 ) 5 me O 2-Me-Phenyl 261 me me me S 2-Me-Phenyl 262 me et me S 2-Me-Phenyl 263 (CH 2 ) 4 me S 2-Me-Phenyl 264 (CH 2 ) 5 me S 2-Me-Phenyl 265 me me me CH 2 CH 2 2-Me-Phenyl 266 me et me CH 2 CH 2 2-Me-Phenyl 267 (CH 2 ) 4 me CH 2 CH 2 2-Me-Phenyl 268 (CH 2 ) 5 me CH 2 CH 2 2-Me-Phenyl 269 me me me CH 2 = CH 2 2-Me-Phenyl 270 me et me CH 2 = CH 2 2-Me-Phenyl 271 (CH 2 ) 4 me CH 2 = CH 2 2-Me-Phenyl 272 (CH 2 ) 5 me CH 2 = CH 2 2-Me-Phenyl 273 me me me O 4-MeO-Phenyl 274 me et me O 4-MeO-Phenyl 275 (CH 2 ) 4 me O 4-MeO-Phenyl 276 (CH 2 ) 5 me O 4-MeO-Phenyl 277 me me me S 4-MeO-Phenyl 278 me et me S 4-MeO-Phenyl 279 (CH 2 ) 4 me S 4-MeO-Phenyl 280 (CH 2 ) 5 me S 4-MeO-Phenyl 281 me me me CH 2 CH 2 4-MeO-Phenyl 282 me et me CH 2 CH 2 4-MeO-Phenyl 283 (CH 2 ) 4 me CH 2 CH 2 4-MeO-Phenyl 284 (CH 2 ) 5 me CH 2 CH 2 4-MeO-Phenyl 285 me me me CH 2 = CH 2 4-MeO-Phenyl 286 me et me CH 2 = CH 2 4-MeO-Phenyl 287 (CH 2 ) 4 me CH 2 = CH 2 4-MeO-Phenyl 288 (CH 2 ) 5 me CH 2 = CH 2 4-MeO-Phenyl 289 me me me O 3-Ph-O-phenyl 290 me et me O 3-Ph-O-phenyl 291 (CH 2 ) 4 me O 3-Ph-O-phenyl 292 (CH 2 ) 5 me O 3-Ph-O-phenyl 293 me me me S 3-Ph-O-phenyl 294 me et me S 3-Ph-O-phenyl 295 (CH 2 ) 4 me S 3-Ph-O-phenyl 296 (CH 2 ) 5 me S 3-Ph-O-phenyl 297 me me me CH 2 CH 2 3-Ph-O-phenyl 298 me et me CH 2 CH 2 3-Ph-O-phenyl 299 (CH 2 ) 4 me CH 2 CH 2 3-Ph-O-phenyl 300 (CH 2 ) 5 me CH 2 CH 2 3-Ph-O-phenyl 301 me me me CH 2 = CH 2 3-Ph-O-phenyl 302 me et me CH 2 = CH 2 3-Ph-O-phenyl 303 (CH 2 ) 4 me CH 2 = CH 2 3-Ph-O-phenyl 304 (CH 2 ) 5 me CH 2 = CH 2 3-Ph-O-phenyl 305 me me me O 3- (EtO-C (Me) Pr) -phenyl 306 me et me O 3- (EtO-C (Me) Pr) -phenyl 307 (CH 2 ) 4 me O 3- (EtO-C (Me) Pr) -phenyl 308 (CH 2 ) 5 me O 3- (EtO-C (Me) Pr) -phenyl 309 me me me S 3- (EtO-C (Me) Pr) -phenyl 310 me et me S 3- (EtO-C (Me) Pr) -phenyl 311 (CH 2 ) 4 me S 3- (EtO-C (Me) Pr) -phenyl 312 (CH 2 ) 5 me S 3- (EtO-C (Me) Pr) -phenyl 313 me me me CH 2 CH 2 3- (EtO-C (Me) Pr) -phenyl 314 me et me CH 2 CH 2 3- (EtO-C (Me) Pr) -phenyl 315 (CH 2 ) 4 me CH 2 CH 2 3- (EtO-C (Me) Pr) -phenyl 316 (CH 2 ) 5 me CH 2 CH 2 3- (EtO-C (Me) Pr) -phenyl 317 me me me CH 2 = CH 2 3- (EtO-C (Me) Pr) -phenyl 318 me et me CH 2 = CH 2 3- (EtO-C (Me) Pr) -phenyl 319 (CH 2 ) 4 me CH 2 = CH 2 3- (EtO-C (Me) Pr) -phenyl 320 (CH 2 ) 5 me CH 2 = CH 2 3- (EtO-C (Me) Pr) -phenyl 321 me iPr me O 3-Br-5-F-phenyl 322 me me me binding 3-Br-5-F-phenyl 323 me et me binding 3-Br-5-F-phenyl 324 (CH 2 ) 4 me binding 3-Br-5-F-phenyl 325 (CH 2 ) 5 me binding 3-Br-5-F-phenyl 326 me me me O 3-Br-5-Cl-phenyl 327 me et me O 3-Br-5-Cl-phenyl 328 me iPr me O 3-Br-5-Cl-phenyl 329 (CH 2 ) 4 me O 3-Br-5-Cl-phenyl 330 (CH 2 ) 5 me O 3-Br-5-Cl-phenyl 331 me me me S 3-Br-5-Cl-phenyl 332 me me me binding 3-Br-5-Cl-phenyl 333 me et me binding 3-Br-5-Cl-phenyl 334 (CH 2 ) 4 me binding 3-Br-5-Cl-phenyl 335 (CH 2 ) 5 me binding 3-Br-5-Cl-phenyl 336 me me me O 2-F-phenyl 337 me et me O 2-F-phenyl 338 (CH 2 ) 4 me O 2-F-phenyl 339 (CH 2 ) 5 me O 2-F-phenyl 340 me me me S 2-F-phenyl 341 me et me S 2-F-phenyl 342 (CH 2 ) 4 me S 2-F-phenyl 343 (CH 2 ) 5 me S 2-F-phenyl 344 me me me CH 2 CH 2 2-F-phenyl 345 me et me CH 2 CH 2 2-F-phenyl 346 (CH 2 ) 4 me CH 2 CH 2 2-F-phenyl 347 (CH 2 ) 5 me CH 2 CH 2 2-F-phenyl 348 me me me CH 2 = CH 2 2-F-phenyl 349 me et me CH 2 = CH 2 2-F-phenyl 350 (CH 2 ) 4 me CH 2 = CH 2 2-F-phenyl 351 (CH 2 ) 5 me CH 2 = CH 2 2-F-phenyl 352 me me me binding 2-F-phenyl 353 me et me binding 2-F-phenyl 354 (CH 2 ) 4 me binding 2-F-phenyl 355 (CH 2 ) 5 me binding 2-F-phenyl 356 me pr me O 4-Br-3-iPr-phenyl 357 me me me binding 4-Br-3-iPr-phenyl 358 me et me binding 4-Br-3-iPr-phenyl 359 (CH 2 ) 4 me binding 4-Br-3-iPr-phenyl 360 (CH 2 ) 5 me binding 4-Br-3-iPr-phenyl 361 me me me binding 4-Cl-3-CF 3 -phenyl 362 me et me binding 4-Cl-3-CF 3 -phenyl 363 (CH 2 ) 4 me binding 4-Cl-3-CF 3 -phenyl 364 (CH 2 ) 5 me binding 4-Cl-3-CF 3 -phenyl 365 me me me O 4-F-3-CF 3 -phenyl 366 me et me O 4-F-3-CF 3 -phenyl 367 me iPr me O 4-F-3-CF 3 -phenyl 368 (CH 2 ) 4 me O 4-F-3-CF 3 -phenyl 369 (CH 2 ) 4 me O 4-F-3-CF 3 -phenyl 370 me me me O 5-F-3-CF 3 -phenyl 371 me et me O 5-F-3-CF 3 -phenyl 372 (CH 2 ) 4 me O 5-F-3-CF 3 -phenyl 373 (CH 2 ) 5 me O 5-F-3-CF 3 -phenyl 374 me me me O 4-Cl-3-CF 3 -phenyl 375 me me me binding 4-Cl-3-CF 3 -phenyl 376 me et me binding 4-Cl-3-CF 3 -phenyl 377 (CH 2 ) 4 me binding 4-Cl-3-CF 3 -phenyl 378 (CH 2 ) 5 me binding 4-Cl-3-CF 3 -phenyl 379 me me me O 4-F-3-CF 3 -phenyl 380 me et me O 4-F-3-CF 3 -phenyl 381 me iPr me O 4-F-3-CF 3 -phenyl 382 (CH 2 ) 4 me O 4-F-3-CF 3 -phenyl 383 (CH 2 ) 4 me O 4-F-3-CF 3 -phenyl 384 me me me O 5-F-3-CF 3 -phenyl 385 me et me O 5-F-3-CF 3 -phenyl 386 (CH 2 ) 4 me O 5-F-3-CF 3 -phenyl 387 (CH 2 ) 5 me O 5-F-3-CF 3 -phenyl 388 me et Cl O 4-Cl-3-tBu-phenyl 389 me me me binding 4-Cl-3-tBu-phenyl 390 me et me binding 4-Cl-3-tBu-phenyl 391 (CH 2 ) 4 me binding 4-Cl-3-tBu-phenyl 392 (CH 2 ) 5 me binding 4-Cl-3-tBu-phenyl 393 me me me binding 4-Cl-2-Me-Phenyl 394 me et me binding 4-Cl-2-Me-Phenyl 395 (CH 2 ) 4 me binding 4-Cl-2-Me-Phenyl 396 (CH 2 ) 5 me binding 4-Cl-2-Me-Phenyl 397 me me me binding 4-Cl-3-Me-Phenyl 398 me et me binding 4-Cl-3-Me-Phenyl 399 (CH 2 ) 4 me binding 4-Cl-3-Me-Phenyl 400 (CH 2 ) 5 me binding 4-Cl-3-Me-Phenyl 401 me iPr me O 4-Cl-3-iPr-phenyl 402 me cPr Cl O 4-Cl-3-iPr-phenyl 403 me me me binding 4-Cl-3-iPr-phenyl 404 me et me binding 4-Cl-3-iPr-phenyl 405 (CH 2 ) 4 me binding 4-Cl-3-iPr-phenyl 406 (CH 2 ) 5 me binding 4-Cl-3-iPr-phenyl 407 me et me O 4-Cl-6-iPr-pyridin-2-yl 408 me me me CH 2 CH 2 4-Cl-6-iPr-pyridin-2-yl 409 me et me CH 2 CH 2 4-Cl-6-iPr-pyridin-2-yl 410 (CH 2 ) 4 me CH 2 CH 2 4-Cl-6-iPr-pyridin-2-yl 411 (CH 2 ) 5 me CH 2 CH 2 4-Cl-6-iPr-pyridin-2-yl 412 me me me binding 4-Cl-6-iPr-pyridin-2-yl 413 me et me binding 4-Cl-6-iPr-pyridin-2-yl 414 (CH 2 ) 4 me binding 4-Cl-6-iPr-pyridin-2-yl 415 (CH 2 ) 5 me binding 4-Cl-6-iPr-pyridin-2-yl 416 (CH 2 ) 5 me S 3- (2-Cl-pyridin-3-yl) -phenyl 417 me me me CH 2 = CH 2 3- (2-Cl-pyridin-3-yl) -phenyl 418 me et me CH 2 = CH 2 3- (2-Cl-pyridin-3-yl) -phenyl 419 (CH 2 ) 4 me CH 2 = CH 2 3- (2-Cl-pyridin-3-yl) -phenyl 420 (CH 2 ) 5 me CH 2 = CH 2 3- (2-Cl-pyridin-3-yl) -phenyl 421 me me me CH 2 CH 2 3- (2-Cl-pyridin-3-yl) -phenyl 422 me et me CH 2 CH 2 3- (2-Cl-pyridin-3-yl) -phenyl 423 (CH 2 ) 4 me CH 2 CH 2 3- (2-Cl-pyridin-3-yl) -phenyl 424 (CH 2 ) 5 me CH 2 CH 2 3- (2-Cl-pyridin-3-yl) -phenyl 425 me et me binding 3- (2-Cl-pyridin-3-yl) -phenyl 426 (CH 2 ) 4 me binding 3- (2-Cl-pyridin-3-yl) -phenyl 427 (CH 2 ) 5 me binding 3- (2-Cl-pyridin-3-yl) -phenyl 428 me me me binding 3-CF 3 -4-Me-phenyl 429 me et me binding 3-CF 3 -4-Me-phenyl 430 (CH 2 ) 4 me binding 3-CF 3 -4-Me-phenyl 431 (CH 2 ) 5 me binding 3-CF 3 -4-Me-phenyl 432 me me me binding 4-F-3-OCF 3 -phenyl 433 me et me binding 4-F-3-OCF 3 -phenyl 434 (CH 2 ) 4 me binding 4-F-3-OCF 3 -phenyl 435 (CH 2 ) 5 me binding 4-F-3-OCF 3 -phenyl 436 me me me binding 3-I-5-CF 3 -phenyl 437 me et me binding 3-I-5-CF 3 -phenyl 438 (CH 2 ) 4 me binding 3-I-5-CF 3 -phenyl 439 (CH 2 ) 5 me binding 3-I-5-CF 3 -phenyl 440 me iPr me O 3-tBu-phenyl 441 me me me binding 3-tBu-phenyl 442 me et me binding 3-tBu-phenyl 443 (CH 2 ) 4 me binding 3-tBu-phenyl 444 (CH 2 ) 5 me binding 3-tBu-phenyl 445 me me me binding 4-tBu-phenyl 446 me et me binding 4-tBu-phenyl 447 (CH 2 ) 4 me binding 4-tBu-phenyl 448 (CH 2 ) 5 me binding 4-tBu-phenyl 449 me me me binding 4-CN-3-CF 3 -phenyl 450 me et me binding 4-CN-3-CF 3 -phenyl 451 (CH 2 ) 4 me binding 4-CN-3-CF 3 -phenyl 452 (CH 2 ) 5 me binding 4-CN-3-CF 3 -phenyl 453 me me me binding 4-CF 3 -phenyl 454 me et me binding 4-CF 3 -phenyl 455 (CH 2 ) 4 me binding 4-CF 3 -phenyl 456 (CH 2 ) 5 me binding 4-CF 3 -phenyl 457 me me me binding 2-Me-Phenyl 458 me et me binding 2-Me-Phenyl 459 (CH 2 ) 4 me binding 2-Me-Phenyl 460 (CH 2 ) 5 me binding 2-Me-Phenyl 461 me me me binding 4-MeO-Phenyl 462 me et me binding 4-MeO-Phenyl 463 (CH 2 ) 4 me binding 4-MeO-Phenyl 464 (CH 2 ) 5 me binding 4-MeO-Phenyl 465 me me me binding 3-Ph-O-phenyl 466 me et me binding 3-Ph-O-phenyl 467 (CH 2 ) 4 me binding 3-Ph-O-phenyl 468 (CH 2 ) 5 me binding 3-Ph-O-phenyl 469 me me me binding 3- (EtO-C (Me) Pr) -phenyl 470 me me me binding 3- (EtO-C (Me) Pr) -phenyl 471 (CH 2 ) 4 me binding 3- (EtO-C (Me) Pr) -phenyl 472 (CH 2 ) 5 me binding 3- (EtO-C (Me) Pr) -phenyl 473 me me me O 3- (MeO-C (Me) Pr) -phenyl 474 me et me O 3- (MeO-C (Me) Pr) -phenyl 475 (CH 2 ) 4 me O 3- (MeO-C (Me) Pr) -phenyl 476 (CH 2 ) 5 me O 3- (MeO-C (Me) Pr) -phenyl 477 me me me O 3- (EtO-C (Me) (H 2 C = C)) - phenyl 478 me et me O 3- (EtO-C (Me) (H 2 C = C)) - phenyl 479 (CH 2 ) 4 me O 3- (EtO-C (Me) (H 2 C = C)) - phenyl 480 (CH 2 ) 5 me O 3- (EtO-C (Me) (H 2 C = C)) - phenyl 481 me me me O 3- (EtO-C (Me) (H 2 C = C (Me) CH 2 )) - phenyl 482 me et me O 3- (EtO-C (Me) (H 2 C = C (Me) CH 2 )) - phenyl 483 (CH 2 ) 4 me O 3- (EtO-C (Me) (H 2 C = C (Me) CH 2 )) - phenyl 484 (CH 2 ) 5 me O 3- (EtO-C (Me) (H 2 C = C (Me) CH 2 )) - phenyl 485 me me me O 3- (MeO-C (Me) (H 2 C = C (Me) CH 2 )) - phenyl 486 me et me O 3- (MeO-C (Me) (H 2 C = C (Me) CH 2 )) - phenyl 487 (CH 2 ) 4 me O 3- (MeO-C (Me) (H 2 C = C (Me) CH 2 )) - phenyl 488 (CH 2 ) 5 me O 3- (MeO-C (Me) (H 2 C = C (Me) CH 2 )) - phenyl 489 me me me O 3- (MeO-C (Me) (H 2 C = CHCH 2 )) - phenyl 490 me et me O 3- (MeO-C (Me) (H 2 C = CHCH 2 )) - phenyl 491 (CH 2 ) 4 me O 3- (MeO-C (Me) (H 2 C = CHCH 2 )) - phenyl 492 (CH 2 ) 5 me O 3- (MeO-C (Me) (H 2 C = CHCH 2 )) - phenyl 493 me me me O 3- (HO-C (Me) (H 2 C = CHCH 2 )) - phenyl 494 me et me O 3- (HO-C (Me) (H 2 C = CHCH 2 )) - phenyl 495 (CH 2 ) 4 me O 3- (HO-C (Me) (H 2 C = CHCH 2 )) - phenyl 496 (CH 2 ) 5 me O 3- (HO-C (Me) (H 2 C = CHCH 2 )) - phenyl 497 me me me O 3- (EtO-C (Me) (H 2 C = CHCH 2 )) - phenyl 498 me et me O 3- (EtO-C (Me) (H 2 C = CHCH 2 )) - phenyl 499 (CH 2 ) 4 me O 3- (EtO-C (Me) (H 2 C = CHCH 2 )) - phenyl 500 (CH 2 ) 5 me O 3- (EtO-C (Me) (H 2 C = CHCH 2 )) - phenyl 501 me me me O 3- (MeO-C (Me)) Et-phenyl 502 me et me O 3- (MeO-C (Me)) Et-phenyl 503 (CH 2 ) 4 me O 3- (MeO-C (Me)) Et-phenyl 504 (CH 2 ) 5 me O 3- (MeO-C (Me)) Et-phenyl 505 me me me O 3- (4,5-dimethyl-1,3-dioxolan-2-yl) -phenyl 506 me et me O 3- (4,5-dimethyl-1,3-dioxolan-2-yl) -phenyl 507 (CH 2 ) 4 me O 3- (4,5-dimethyl-1,3-dioxolan-2-yl) -phenyl 508 (CH 2 ) 5 me O 3- (4,5-dimethyl-1,3-dioxolan-2-yl) -phenyl 509 me me me binding 3- (4,5-dimethyl-1,3-dioxolan-2-yl) -phenyl 510 me et me binding 3- (4,5-dimethyl-1,3-dioxolan-2-yl) -phenyl 511 (CH 2 ) 4 me binding 3- (4,5-dimethyl-1,3-dioxolan-2-yl) -phenyl 512 (CH 2 ) 5 me binding 3- (4,5-dimethyl-1,3-dioxolan-2-yl) -phenyl 513 me me me O 3- (tBu-carbonyl) -phenyl 514 me et me O 3- (tBu-carbonyl) -phenyl 515 (CH 2 ) 4 me O 3- (tBu-carbonyl) -phenyl 516 (CH 2 ) 5 me O 3- (tBu-carbonyl) -phenyl 517 me me me binding 3- (tBu-carbonyl) -phenyl 518 me et me binding 3- (tBu-carbonyl) -phenyl 519 (CH 2 ) 4 me binding 3- (tBu-carbonyl) -phenyl 520 (CH 2 ) 5 me binding 3- (tBu-carbonyl) -phenyl 521 me me me O 3- (tBu-O-carbonyl) -phenyl 522 me et me O 3- (tBu-O-carbonyl) -phenyl 523 (CH 2 ) 4 me O 3- (tBu-O-carbonyl) -phenyl 524 (CH 2 ) 5 me O 3- (tBu-O-carbonyl) -phenyl 525 me me me binding 3- (tBu-O-carbonyl) -phenyl 526 me et me binding 3- (tBu-O-carbonyl) -phenyl 527 (CH 2 ) 4 me binding 3- (tBu-O-carbonyl) -phenyl 528 (CH 2 ) 5 me binding 3- (tBu-O-carbonyl) -phenyl 529 me me me O 3- (HO-C (Me) (iPr) -phenyl 530 me et me O 3- (HO-C (Me) (iPr) -phenyl 531 (CH 2 ) 4 me O 3- (HO-C (Me) (iPr) -phenyl 532 (CH 2 ) 5 me O 3- (HO-C (Me) (iPr) -phenyl 533 me me me O 3- (HO-C (Me) (tBu) -phenyl 534 me et me O 3- (HO-C (Me) (tBu) -phenyl 535 (CH 2 ) 4 me O 3- (HO-C (Me) (tBu) -phenyl 536 (CH 2 ) 5 me O 3- (HO-C (Me) (tBu) -phenyl 537 me me me O 2-naphthyl 538 me et me O 2-naphthyl 539 me et me O 2-naphthyl 540 (CH 2 ) 4 me O 2-naphthyl 541 (CH 2 ) 5 me O 2-naphthyl 542 me et me binding 2-naphthyl 543 me me me binding 2-naphthyl 544 (CH 2 ) 4 me binding 2-naphthyl 545 (CH 2 ) 5 me binding 2-naphthyl 546 me me me O (4-iPr) -thia-3,5-diazole-2-yl 547 me et me O (4-iPr) -thia-3,5-diazole-2-yl 548 (CH 2 ) 4 me O (4-iPr) -thia-3,5-diazole-2-yl 549 (CH 2 ) 5 me O (4-iPr) -thia-3,5-diazole-2-yl 550 me me me O 2,4-dichloro-thiazol-5-yl 551 me et me O 2,4-dichloro-thiazol-5-yl 552 (CH 2 ) 4 me O 2,4-dichloro-thiazol-5-yl 553 (CH 2 ) 5 me O 2,4-dichloro-thiazol-5-yl 554 me me me OCH 2 2,4-dichloro-thiazol-5-yl 555 me et me OCH 2 2,4-dichloro-thiazol-5-yl 556 (CH 2 ) 4 me OCH 2 2,4-dichloro-thiazol-5-yl 557 (CH 2 ) 5 me OCH 2 2,4-dichloro-thiazol-5-yl 558 me me me O S-Cl-4-tBu-thiazol-2-yl 559 me et me O S-Ck-4-tBu-thiazol-2-yl
                             
  • Table 2 lists some of the compounds according to the invention mentioned in Table 1 in their salt form. Table 2 No. salt R2 R3 R5 A R6 34 trifluoromethanesulfonate me et me O 4-Cl-3-CF 3 -phenyl 366 hydrochloride me et me O 4-F-3-CF 3 -phenyl 371 trifluoroacetate me et me O 5-F-3-CF 3 -phenyl 371 trifluoroacetate me et me O 5-F-3-CF 3 -phenyl 373 trifluoroacetate (CH 2 ) 5 me O 5-F-3-CF 3 -phenyl 373 hydrobromide (CH 2 ) 5 me O 5-F-3-CF 3 -phenyl 373 trifluoroacetate (CH 2 ) 5 me O 5-F-3-CF 3 -phenyl 538 acetate me et me O 2-naphthyl
  • Table 3 gives log P data for some compounds for further characterization. The log P data were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a reversed-phase column (C18) using the following methods:
    Temperature: 40 ° C; Mobile phase: 0.1% or 0.06% aqueous formic acid or 0.1% aqueous Phos phosphoric acid and acetonitrile; linear gradient from 10% acetonitrile to 90% or 95% acetonitrile.
  • The Calibration was performed using unbranched alkane-2-ones (consisting of 3 to 13 or 16 carbon atoms) with known logP values (determination of the logP values over the retention times by means of linear interpolation between two consecutive alkanones).
  • The lambda max values were determined over the maxima of the chromatographic signals of the UV spectrums from 190 nm to 400 or 450 nm. Table 3
    Figure 00340001
    Figure 00350001
    • 1) 2.5 (Me-butenyl), 3 (Me-amidine), 5.07-5.17 (m, CH 2 -olefinic butenyl)
    • 2) 1.19-1.28 (triplet CH 2 of OEt), 2.51 (Me-butenyl), 3 (Me-amidine), 4.94-5.0 (m, CH 2 -olefinic butenyl).
  • A. Formulation Examples
  • 1. Dusts
  • One Dust is obtained by adding 10 parts by weight of a Compound of general formula (I) and 90 parts by weight of talcum as Inertstoff mixed and crushed in a hammer mill.
  • 2. Dispersible powder
  • One water-dispersible, wettable powder is obtained by 25 parts by weight of a compound of the general formula (I), 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight lignosulfonic acid potassium and 1 part by weight of oleoylmethyltaurine acid Sodium as wetting and dispersing mixes and in a pin mill served basis.
  • 3. Dispersion concentrate
  • An easily water-dispersible dispersion concentrate is obtained by mixing 20 parts by weight of a compound of general formula (I), 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 Parts of paraffinic mineral oil (boiling range, for example, about 255 to about 277 ° C) mixed and ground in a ball mill to a fineness of less than 5 microns.
  • 4. Emulsifiable concentrate
  • One emulsifiable concentrate is obtained from 15 parts by weight of a Compound of general formula (I), 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as an emulsifier.
  • 5. Water-dispersible granules
  • A water-dispersible granule is obtained by
    75 parts by weight of a compound of general formula (I),
    10 parts by weight of lignosulfonic acid calcium,
    5 parts by weight of sodium lauryl sulfate,
    3 parts by weight of polyvinyl alcohol and
    7 parts by weight kaolin
    milled, ground on a pin mill and granulated the powder in a fluidized bed by spraying water as Granulierflüssigkeit.
  • A water-dispersible granule is also obtained by
    25 parts by weight of a compound of general formula (I),
    5 parts by weight of sodium 2,2'-dinaphthylmethane-6,6'-disulfonate,
    2 parts by weight oleoylmethyltaurine acid sodium,
    1 part by weight of polyvinyl alcohol,
    17 parts by weight of calcium carbonate and
    50 parts by weight of water
    Homogenized on a colloid mill and pre-crushed, then ground on a bead mill and the suspension thus obtained in a spray tower by means of a Einstoffdüse atomized and dried.
  • B. Biological Examples
  • 1. Pre-emergence herbicidal action
  • seed of mono- or dicotyledonous weeds or crop plants are in Wood fiber pots in sandy loam and designed with Covered earth. In the form of wettable powders (WP) or as Emulsion Concentrates (EC) formulated compounds of the formula (I) are then used as an aqueous suspension with an amount of water of the equivalent of 800 l / ha with the addition of 0.2% wetting agent on the Surface of the cover soil applied.
  • After the treatment, the pots are placed in the greenhouse and kept under good growth conditions for the test plants. The visual assessment of the damage to the test plants is carried out after a test period of 3 weeks in comparison to untreated controls (herbicidal action in percent (%): 100% effect = plants are dead, 0% effect = like control plants). In this case, for example, the compounds at an application rate of 1.28 kg / ha each showed at least 80% action against the particular named harmful plants:
    No. 114 against DIGSA, SETVI, CHEAL and VERPE,
    No. 290 against DIGSA, AMARE, SETVI and VERPE,
    No. 306 against SETVI, AMARE, MATCH and VERPE,
    No. 345 against DIGSA, SETVI, CHEAL and MATCH,
    No. 362 against DIGSA, SETVI and VERPE,
    No. 364 against DIGSA, SETVI, ABUTH, AMARE, VERPE and VIOSS,
    No. 478 against ECHCG, SETVI and VERPE,
    No. 506 against ABUTH, VERPE and VIOSS,
    No. 547 against DIGSA, ECHCG, SETVI, AMARE, CHEAL, GALAP and VIOSS,
  • 2. Post-emergence herbicidal action
  • 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 of the formula (I) formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then sprayed onto the green parts of plants as an aqueous suspension having a water consumption of about 800 l / ha with the addition of 0.2% wetting agent. After about 3 weeks of life of the test plants in the greenhouse under optimal growth conditions, the effect of the preparations is scored visually compared to untreated controls (herbicidal activity in percent (%): 100% effect = plants are dead, 0% effect = like control plants). In this case, for example, the compounds at an application rate of 1.28 kg / ha each showed at least 80% action against the particular named harmful plants:
    No. 36 against ABUTH, AMARE, CHEAL, PHBPU, VERPE and XANST,
    No. 130 against ABUTH and VERPE,
    No 290 against ECHCG, ABUTH, AMARE, CHEAL, PHBPU, VERPE and SETVI,
    No 362 against ECHCG, ABUTH, AMARE, CHEAL, PHBPU and VERPE,
    No. 364 against ECHCG, ABUTH, AMARE, CHEAL, PHBPU, VERPE and SETVI,
    No. 365 against ECHCG, CHEAL, GALAP, PHBPU and POLSS,
    No. 371 against ABUTH, GALAP, PHBPU and VERPE,
    No. 401 against ECHCG, ABUTH, AMARE, VERPE, VIOSS and XANST,
    No. 474 against ABUTH, AMARE, GALAP, PHBPU VERPE and VIOSS,
    No. 506 against VERPE and VIOSS,
    No. 522 against VERPE and VIOSS,
    No. 530 against AMARE, VERPE and VIOSS.
  • The abbreviations mean
  • ABUTH
    Abutilon theophrasti
    CHEAL
    Chenopodium album
    ECHCG
    Echinochloa crus galli
    MATCH
    Matricaria chamomilla
    SETVI
    Setaria viridis
    VIOSS
    Viola spec.
    AMARE
    Amaranthus retroflexus
    DIGSA
    Digitaria sanguinalis
    GALAP
    Galium aparine
    PHBPU
    Pharitis purpureum
    VERPE
    Veronica persica
    XANST
    Xanthium strumarium
  • QUOTES INCLUDE IN THE DESCRIPTION
  • This list The documents listed by the applicant have been automated generated and is solely for better information recorded by the reader. The list is not part of the German Patent or utility model application. The DPMA takes over no liability for any errors or omissions.
  • Cited patent literature
    • - EP 1150944 B1 [0002, 0020]
    • EP 0221044 A [0026]
    • EP 0131624A [0026]
    • WO 92/11376 [0026]
    • WO 92/14827 [0026]
    • WO 91/19806 [0026]
    • - EP 0242236 A [0026]
    • - EP 0242246 A [0026]
    • WO 92/00377 [0026]
    • EP 0257993 A [0026]
    • - US 5013659 A [0026]
    • EP 0142924A [0026]
    • EP 0193259A [0026]
    • WO 91/13972 [0026]
  • Cited non-patent literature
    • Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd Ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY [0027]
    • Winnacker "Genes and Clones", VCH Weinheim 2nd edition 1996 or Christou, "Trends in Plant Science" 1 (1996) 423-431 [0027]
    • Braun et al., EMBO J. 11 (1992), 3219-3227 [0030]
    • Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850 [0030]
    • Sonnewald et al., Plant J. 1 (1991), 95-106 [0030]
    • - Winnacker-Kuchler, "Chemical Technology", Volume 7, C. Hauser Verlag Munich, 4th ed., 1986 [0034]
    • - Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, NY, 1973 [0034]
    • - K. Martens, "Spray Drying" Handbook, 3rd ed. 1979, G. Goodwin Ltd. London [0034]
    • - Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd ed., Darland Books, Caldwell NJ, H. v. Olphen, "Introduction to Clay Colloid Chemistry"; 2nd Ed., J. Wiley & Sons, NY; C. Marsden, "Solvents Guide"; 2nd Ed., Interscience, NY 1963 [0035]
    • McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood NJ; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964 [0035]
    • - Schönfeldt, "Grenzflächenaktive Äthylenoxidaddukte", Wiss. Publishing Company, Stuttgart 1976 [0035]
    • - Winnacker-Kuchler, "Chemical Technology", Volume 7, C. Hauser Verlag Munich, 4th ed., 1986 [0035]
    • - "Spray-Drying Handbook" 3rd Ed. 1979, G. Goodwin Ltd., London [0041]
    • - JE Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 ff. [0041]
    • "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Rill, New York 1973, pp. 8-57 [0041]
    • GC Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pp. 81-96 [0041]
    • JD Freyer, SA Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103 [0041]
    • Weed Research 26, 441-445 (1986) [0045]
    • - The Pesticide Manual, 13th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2003 [0045]

Claims (8)

  1. Use of compounds of the formula (I), or salts thereof, as herbicides
    Figure 00390001
    in which R 2 and R 3 are each independently (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, halogen (C 1 -C 6 ) - alkyl, halo (C 2 -C 6 ) -alkenyl, halo (C 2 -C 6 ) -alkynyl, (C 1 -C 4 ) -alkoxy (C 1 -C 6 ) -alkyl, (C 1 -) C 4 ) -alkoxy- (C 2 -C 6 ) -alkenyl, (C 1 -C 4 ) -alkoxy- (C 2 -C 6 ) -alkynyl, or R 2 and R 3 together denote (CH 2 ) 4 or (CH 2 ) 5 , or R 2 and R 3 together with the nitrogen atom to which they are attached form a 5- or 6-membered saturated, partially saturated, unsaturated or aromatic ring containing k heteroatoms from the group consisting of oxygen, nitrogen and Contains sulfur and is substituted by p radicals from the group halogen, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, nitro, cyano and hydroxy, R 4 and R 5 are each independently (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, halogen, cyano, hydroxyl, mercapto, acyl, OR a , SR a , Si ( R a ) 3 halogen (C 1 -C 6 ) -alkyl, (C 1 -C 4 ) -alkoxy- (C 1 -C 6 ) -alkyl or heterocyclyl bonded via a carbon atom to phenyl, R a is (C 1 -C 8 ) -alkyl, m is 0, 1, 2 or 3, R 6 are each represented by n radicals from the group halogen, cyano, phenoxy, (C 1 -C 8 ) -alkylcarbonyl, (C 1 -C 8 ) -alkoxycarbonyl, (C 1 -C 8 ) Alkyl, (C 1 -C 8 ) alkoxy, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl and 1,3-dioxolan-2yl substituted carbocyclyl or heterocyclyl, wherein said radicals (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy, (C 2 -C 8 ) -alkenyl and (C 2 -C 8 ) -alkynyl by n radicals from the group (C 1 -C 8 ) alkoxy, hydroxy and halogen are substituted, and 1,3-dioxolan-2y is substituted by n radicals (C 1 -C 8 ) alkyl, A is a bond or a divalent group -O-, -S (O ) n -, -NR 9 , -CR 7 = CR 7 -, -C≡C-, -A 1 -, -A 1 -A 1 -, -A 2 -, -A 3 -, -A 1 O- , -A 1 S (O) n -, -OA 2 -, -NR 9 -A 2 -, -OA 2 -A 1 -, -OA 2 -CR 7 = CR 8 -, -S (O) n - A 1 -, - (CH 2 ) 2 -ON = CR 8 -, -XA 2 -NH-, -C (R 8 ) = NO- (C 1 -C 6 ) alkyl or -O (A 1 ) k O-, A 1 is -CHR 7 -, A 2 is -C (= X) -, A 3 is CR 8 = NO-, X is oxygen or sulfur , R 7 is hydrogen, halogen, cyano, (C 1 -C 6 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, phenyl, halogen, cyano, hydroxy, mercapto, halogeno (C 1 -C 6 ) -alkyl or (C 1 -C 4 ) -alkoxy- (C 1 -C 6 ) -alkyl, R 8 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, ( C 2 -C 6 ) -alkynyl, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkylthio, (C 3 -C 6 ) -cycloalkyl, phenyl, halogen, cyano, hydroxy, mercapto , Halogen (C 1 -C 6 ) -alkyl, (C 1 -C 4 ) -alkoxy- (C 1 -C 6 ) -alkyl, carbocyclyl or heterocyclyl, R 9 is hydrogen, (C 1 -C 6 ) - Alkyl, carbocyclyl or heterocyclyl, k is 1, 2 or 3, n is 0, 1 or 2, and p is 0, 1, 2 or 3.
  2. Use of compounds of the general formula (I) according to Claim 1, in which R 2 and R 3 are each independently (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) Alkynyl, halo (C 1 -C 6 ) alkyl, halo (C 2 -C 6 ) alkenyl, halo (C 2 -C 6 ) alkynyl, (C 1 -C 4 ) alkoxy ( C 1 -C 6 ) -alkyl, (C 1 -C 4 ) -alkoxy- (C 2 -C 6 ) -alkenyl, (C 1 -C 4 ) -alkoxy- (C 2 -C 6 ) -alkynyl, ( CH 2 ) 4 or (CH 2 ) 5 , R 4 is (C 1 -C 6 ) -alkyl, halogen (C 1 -C 6 ) -alkyl or (C 1 -C 4 ) -alkoxy- (C 1 -) C 6 ) -alkyl, R 5 is halogen, (C 1 -C 6 ) -alkyl, halogen (C 1 -C 6 ) -alkyl or (C 1 -C 4 ) -alkoxy- (C 1 -C 6 ) A, A is a bond, -O-, -S-, -CH 2 CH 2 -, -CH 2 -, -OCH 2 -, -CH = CH-, -C≡C-, -NH-CO- , -N (CH 3 ) -, NH- or -O-CO-NH-, R 6 by n radicals from the group halogen, cyano, phenoxy, (C 1 -C 4 ) alkylcarbonyl, (C 1 -C 4 ) alkyl, (C 1 -C 6 ) alkoxy, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl and 1,3-dioxolan-2yl substituted phenyl or naphthyl, wherein the mentioned radicals (C 1 -C 6 ) alkyl, (C 1 -C 6 ) alkoxy, (C 2 -C 6 ) alkenyl and (C 2 -C 6 ) alkynyl by n radicals from the Group (C 1 -C 4 ) alkoxy, hydroxy and halogen are substituted, and 1,3-dioxolan-2y is substituted by n radicals (C 1 -C 8 ) alkyl, or R 6 by n radicals from the group Halogen, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 4 ) -alkoxy and halogeno (C 1 -C 4 ) -alkyl-substituted heterocyclyl. m is 0 or 1, and n is 0, 1 or 2.
  3. Use of compounds of general formula (I) according to claim 1 or 2, wherein R 2 is methyl, R 3 is methyl, ethyl, cyclopropy or iso-propyl, or R 2 and R 3 together are (CH 2 ) 4 or (CH 2 ) 5 , R 4 is methyl, R 5 is methyl or chlorine, A is a bond, -O-, -S-, -CH 2 -CH 2 -, -CH 2 -, -OCH 2 - or - CH = CH-, R 6 means by n radicals from the group halogen, cyano, phenoxy, (C 1 -C 4 ) -alkylcarbonyl, (C 1 -C 4 ) -alkyl, (C 1 -C 6 ) -alkoxy, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl and 1,3-dioxolan-2yl-substituted phenyl or naphthyl, where the radicals mentioned are (C 1 -C 6 ) -alkyl, (C 1 -) C 6 ) -alkoxy, (C 2 -C 6 ) -alkenyl and (C 2 -C 6 ) -alkynyl are substituted by n radicals from the group consisting of (C 1 -C 4 ) -alkoxy, hydroxy and halogen, and 1, 3-dioxolan-2y is substituted by n radicals (C 1 -C 8 ) -alkyl, or R 6 by n radicals from the group halogen, (C 1 -C 6 ) -alkyl, halogen (C 1 -C 4 ) -alkoxy and halo (C 1 -C 4 ) -alkyl substituents Pyridine, thiadiazolyl or thiazolyl, m is 1, and n is 0, 1 or 2.
  4. Use of compounds of the general formula (I) according to any one of claims 1 to 3 for controlling unwanted plants.
  5. Use according to claim 4, characterized that the compounds of the general formula (I) for controlling undesirable plants used in crops of crops become.
  6. Use according to claim 5, characterized that the crops are transgenic crops.
  7. Method of combating unwanted Plants by using compounds of the general formula (I) according to any one of claims 1 to 6.
  8. A herbicidal composition containing one or more compounds of the formula (I), or salts thereof, according to claims 1 to 3.
DE102007029603A 2007-06-27 2007-06-27 Phenylamidine for herbicide agent, controlling unwanted plants, and for use as herbicides, comprises general formula Withdrawn DE102007029603A1 (en)

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DE102007029603A DE102007029603A1 (en) 2007-06-27 2007-06-27 Phenylamidine for herbicide agent, controlling unwanted plants, and for use as herbicides, comprises general formula
BRPI0808734 BRPI0808734A2 (en) 2007-03-12 2008-03-04 Use of n2-phenylamidines as herbicides
US12/530,767 US20100167926A1 (en) 2007-03-12 2008-03-04 3-substituted phenoxyphenylamidines and use thereof as fungicides
JP2009553038A JP2010520900A (en) 2007-03-12 2008-03-04 Phenoxy-substituted phenylamidine derivatives and their use as fungicides
US12/530,781 US20100113276A1 (en) 2007-03-12 2008-03-04 Use of n2-phenylamidines as herbicides
EP20080716202 EP2144502A2 (en) 2007-03-12 2008-03-04 Use of n2-phenylamidines as herbicides and herbicidal agents comprising the same
EP08716204.6A EP2136628B1 (en) 2007-03-12 2008-03-04 Phenoxy substituted phenylamidine derivatives and their use as fungicides
CN 200880008092 CN101636082B (en) 2007-03-12 2008-03-04 3-substituted phenoxyphenylamidines and use thereof as fungicides
BRPI0808846A BRPI0808846A2 (en) 2007-03-12 2008-03-04 3-substituted phenoxyphenylamidines and their use as fungicides
CA 2680617 CA2680617A1 (en) 2007-03-12 2008-03-04 Use of n2-phenylamidines as herbicides
EP08716205.3A EP2120558B1 (en) 2007-03-12 2008-03-04 3,4-Disubstituted phenoxyphenylamidine derivatives and their use as fungicides
PCT/EP2008/001685 WO2008110280A2 (en) 2007-03-12 2008-03-04 Phenoxy substituted phenylamidine derivatives and their use as fungicides
CN 200880008189 CN101631462B (en) 2007-03-12 2008-03-04 Dihalophenoxyphenylamidines and use thereof as fungicides
AU2008226094A AU2008226094A1 (en) 2007-03-12 2008-03-04 Use of N2-phenylamidines as herbicides and herbicidal agents comprising the same
JP2009553036A JP2010520898A (en) 2007-03-12 2008-03-04 Use of N2-phenylamidine as a herbicide
EP20080716203 EP2136627B1 (en) 2007-03-12 2008-03-04 Dihalophenoxyphenylamidines and use thereof as fungicides
PCT/EP2008/001684 WO2008110279A1 (en) 2007-03-12 2008-03-04 Dihalophenoxyphenylamidines and use thereof as fungicides
US12/530,751 US9199922B2 (en) 2007-03-12 2008-03-04 Dihalophenoxyphenylamidines and use thereof as fungicides
BRPI0808786-5A2A BRPI0808786A2 (en) 2007-03-12 2008-03-04 Di-halogenophenoxyphymylamidines and its use as fungicides
JP2009553037A JP2010520899A (en) 2007-03-12 2008-03-04 Dihalophenoxyphenylamidine and its use as a fungicide
PCT/EP2008/001683 WO2008110278A2 (en) 2007-03-12 2008-03-04 Use of n2-phenylamidines as herbicides and herbicidal agents comprising the same
BRPI0808798-9A2A BRPI0808798A2 (en) 2007-03-12 2008-03-04 3,5-dissubstituted phenoxyphenylamidins and their use as fungicides
US12/530,468 US8080688B2 (en) 2007-03-12 2008-03-04 3, 4-disubstituted phenoxyphenylamidines and use thereof as fungicides
PCT/EP2008/001686 WO2008110281A2 (en) 2007-03-12 2008-03-04 3,4-disubstituted phenoxyphenylamidines and use thereof as fungicides
EA200901109A EA200901109A1 (en) 2007-03-12 2008-03-04 Application of n-phylenamidine as herbicides
ARP080100984 AR065677A1 (en) 2007-03-12 2008-03-10 Utilization n2-phenylamidines herbicidally
US13/358,729 US8394991B2 (en) 2007-03-12 2012-01-26 Phenoxy substituted phenylamidine derivatives and their use as fungicides

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