HERBICIDAL SUBSTITUTED N-TETRAZOLYL ARYL CARBOXAMIDES
20220119358 · 2022-04-21
Inventors
- Christian Waldraff (Bad Vilbel, DE)
- Hartmut AHRENS (Langen, DE)
- Stefan Lehr (Liederbach, DE)
- Elisabeth ASMUS (Hoesbach, DE)
- Hansjoerg Dietrich (Liederbach am Taunus, DE)
- Elmar Gatzweiler (Bad Nauheim, DE)
- Anu Bheemaiah Machettira (Frankfurt am Main, DE)
- Christopher Hugh Rosinger (Hofheim, DE)
Cpc classification
A01N43/713
HUMAN NECESSITIES
A01N25/32
HUMAN NECESSITIES
International classification
C07D257/06
CHEMISTRY; METALLURGY
A01N25/32
HUMAN NECESSITIES
A01N43/713
HUMAN NECESSITIES
Abstract
Arylcarboxamides of the general formula (I) are described as herbicides.
##STR00001##
In this formula (I), IV, X, Y and Z represent radicals such as alkyl and halogen.
Claims
1. An arylcarboxamide of formula (I) or salt thereof. ##STR00020## in which the symbols and indices are defined as follows: R.sup.X is (C.sub.1-C.sub.6)-alkyl or (C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl X is halogen, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, R.sup.1O, R.sup.2(O).sub.nS or R.sup.1O—(C.sub.1-C.sub.6)-alkyl, Y is halogen, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, R.sup.1O or R.sup.2(O).sub.nS, Z is (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.2-C.sub.6)-alkenyl or (C.sub.2-C.sub.6)-alkynyl, R.sup.1 is (C.sub.1-C.sub.6)-alkyl or halo-(C.sub.1-C.sub.6)-alkyl, R.sup.2 is (C.sub.1-C.sub.6)-alkyl, n is 0, 1 or 2.
2. The arylcarboxamide as claimed in claim 1, in which R.sup.X is (C.sub.1-C.sub.3)-alkyl or (C.sub.1-C.sub.3)-alkyl-O—(C.sub.1-C.sub.3)-alkyl, X is halogen, (C.sub.1-C.sub.3)-alkyl, halo-(C.sub.1-C.sub.3)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, R.sup.1O, R.sup.2(O).sub.nS or R.sup.1O—(C.sub.1-C.sub.3)-alkyl, Y is halogen, (C.sub.1-C.sub.4)-alkyl, halo-(C.sub.1-C.sub.4)-alkyl, R.sup.1O or R.sup.2(O).sub.nS, Z is (C.sub.1-C.sub.4)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.2-C.sub.6)-alkenyl or (C.sub.2-C.sub.6)-alkynyl, R.sup.1 is (C.sub.1-C.sub.3)-alkyl or halo-(C.sub.1-C.sub.3)-alkyl, R.sup.2 is (C.sub.1-C.sub.3)-alkyl, n is 0, 1 or 2.
3. The arylcarboxamide as claimed in claim 1, in which R.sup.X is Me, Et or Pr, X is F, Cl, Br, I, Me, Et, c-Pr, CF.sub.3, C.sub.2F.sub.5, CH.sub.2OMe, OMe, SMe, SO2Me, SEt or SO.sub.2Et, Y is Cl, Br, I, Me, CF.sub.3, CHF.sub.2, C.sub.2F.sub.5, SMe or SO.sub.2Me, Z is Me, Et, i-Pr, c-Pr, CH.sub.2-c-Pr, (CH.sub.2).sub.2OMe, allyl or CH.sub.2CF.sub.3, n is 0, 1 or 2.
4. The herbicidal composition or plant growth-regulating composition, wherein it comprises one or more compounds of formula (I) or salts thereof as claimed in claim 1.
5. The herbicidal composition as claimed in claim 4, further comprising a formulation auxiliary.
6. The herbicidal composition as claimed in claim 4, comprising at least one further active ingredient from the group of insecticides, acaricides, herbicides, fungicides, safeners and/or growth regulators.
7. The herbicidal composition as claimed in claim 4, comprising a safener.
8. The herbicidal composition as claimed in claim 7, in which the safener is selected from the group consisting of mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl, benoxacor and dichlorm id.
9. A method of controlling unwanted plants, wherein an effective amount of at least one compound of formula (I) as claimed in claim 1 or an herbicidal composition thereof is applied to a plant or to a site of unwanted vegetation.
10. A product comprising the compound of formula (I) as claimed in claim 1 or an herbicidal composition thereof for controlling unwanted plants.
11. The method as claimed in claim 9, wherein the plant is an unwanted plant in a crop of useful plants.
12. The method as claimed in claim 11, wherein the useful plants are transgenic useful plants.
Description
[0353] Petition: Identification number of the petition. The technical description of the transformation event can be found in the specific petition document available from APHIS on the website via the petition number. These descriptions are hereby disclosed by reference. [0354] Extension of a petition: Reference to an earlier petition for which an extension of scope or term is being requested. [0355] Institution: Name of the person submitting the petition. [0356] Regulated article: The plant species in question. [0357] Transgenic phenotype: The trait imparted to the plant by the transformation event. [0358] Transformation event or line: The name of the event(s) (sometimes also referred to as line(s)) for which nonregulated status is being requested. [0359] APHIS documents: Various documents which have been published by APHIS with regard to the petition or can be obtained from APHIS on request.
[0360] Particularly useful transgenic plants which can be treated in accordance with the invention are plants which comprise one or more genes which code for one or more toxins, for example the transgenic plants which are sold under the following trade names: YIELD GARD® (for example corn, cotton, soya beans), KnockOut® (for example corn), BiteGard® (for example corn), BT-Xtra® (for example corn), StarLink® (for example corn), Bollgard® (cotton), Nucotn® (cotton), Nucotn 33B® (cotton), NatureGard® (for example corn), Protecta® and NewLeaf® (potato). Examples of herbicide-tolerant plants include corn varieties, cotton varieties and soya bean varieties which are available under the following trade names: Roundup Ready® (tolerance to glyphosates, for example corn, cotton, soya beans), Liberty Link® (tolerance to phosphinothricin, for example oilseed rape), IMI® (tolerance to imidazolinone) and SCS® (tolerance to sulfonylurea), for example corn. Herbicide-resistant plants (plants bred in a conventional manner for herbicide tolerance) which may be mentioned include the varieties sold under the name Clearfield® (for example corn).
[0361] Particularly useful transgenic plants which may be treated according to the invention are plants containing transformation events, or a combination of transformation events, and that are listed for example in the databases for various national or regional regulatory agencies (see for example http://gmoinfo.jrc.it/gmp_browse.aspx and http://cera-gmc.org/index.php?evidcode=&hstIDXCode=&gType=&AbbrCode=&atCode=&stCode=&coIDCode=&action=gm_crop_database&mode=Submit).
[0362] The active ingredients or compositions according to the invention can also be used in the protection of materials, for protection of industrial materials against attack and destruction by unwanted microorganisms, for example fungi and insects.
[0363] In addition, the compounds according to the invention can be used as antifouling compositions, alone or in combinations with other active ingredients.
[0364] Industrial materials in the present context are understood as meaning non-living materials which have been prepared for use in industry. For example, industrial materials which are to be protected by active ingredients according to the invention from microbial alteration or destruction may be adhesives, sizes, paper, wallpaper and cardboard, textiles, carpets, leather, wood, paints and plastic articles, cooling lubricants and other materials which can be infected with or destroyed by microorganisms. The range of materials to be protected also includes parts of production plants and buildings, for example cooling water circuits, cooling and heating systems, and ventilation and air conditioning systems, which may be impaired by the proliferation of microorganisms. Industrial materials within the scope of the present invention preferably include adhesives, sizes, paper and cardboard, leather, wood, paints, cooling lubricants and heat transfer fluids, particularly preferably wood. The active ingredients or compositions according to the invention may prevent adverse effects, such as rotting, decay, discoloration, decoloration or formation of mold. In addition, the compounds according to the invention can be used for protection of objects which come into contact with saltwater or brackish water, especially hulls, screens, nets, buildings, moorings and signaling systems, from fouling.
[0365] The method according to the invention for controlling unwanted fungi can also be employed for protecting storage goods. “Storage goods” are understood to mean natural substances of vegetable or animal origin or processing products thereof of natural origin, for which long-term protection is desired. Storage goods of vegetable origin, for example plants or plant parts, such as stems, leaves, tubers, seeds, fruits, grains, can be protected freshly harvested or after processing by (pre)drying, moistening, comminuting, grinding, pressing or roasting. Storage goods also include timber, whether unprocessed, such as construction timber, electricity poles and barriers, or in the form of finished products, such as furniture. Storage goods of animal origin are, for example, hides, leather, furs and hairs. The active ingredients according to the invention may prevent adverse effects, such as rotting, decay, discoloration, decoloration or formation of mold.
[0366] Non-limiting examples of pathogens of fungal diseases which can be treated in accordance with the invention include: Diseases caused by powdery mildew pathogens, for example Blumeria species, for example Blumeria graminis; Podosphaera species, for example Podosphaera leucotricha; Sphaerotheca species, for example Sphaerotheca fuliginea; Uncinula species, for example Uncinula necator; diseases caused by rust disease pathogens, for example Gymnosporangium species, for example Gymnosporangium sabinae; Hemileia species, for example Hemileia vastatrix; Phakopsora species, for example Phakopsora pachyrhizi and Phakopsora meibomiae; Puccinia species, for example Puccinia recondita or Puccinia triticina; Uromyces species, for example Uromyces appendiculatus; diseases caused by pathogens from the group of the Oomycetes, for example Bremia species, for example Bremia lactucae; Peronospora species, for example Peronospora pisi or P. brassicae; Phytophthora species, for example Phytophthora infestans; Plasmopara species, for example Plasmopara viticola; Pseudoperonospora species, for example Pseudoperonospora humuli or Pseudoperonospora cubensis; Pythium species, for example Pythium ultimum;leaf blotch diseases and leaf wilt diseases caused, for example, by Alternaria species, for example Alternaria solani; Cercospora species, for example Cercospora beticola; Cladiosporium species, for example Cladiosporium cucumerinum; Cochliobolus species, for example Cochliobolus sativus (conidia form: Drechslera, syn: Helminthosporium); Colletotrichum species, for example Colletotrichum lindemuthanium; Cycloconium species, for example Cycloconium oleaginum; Diaporthe species, for example Diaporthe citri; Elsinoe species, for example Elsinoe fawcettii; Gloeosporium species, for example Gloeosporium laeticolor; Glomerella species, for example Glomerella cingulata; Guignardia species, for example Guignardia bidwelli; Leptosphaeria species, for example Leptosphaeria maculans; Magnaporthe species, for example Magnaporthe grisea; Microdochium species, for example Microdochium nivale; Mycosphaerella species, for example Mycosphaerelle graminicola and M. fijiensis; Phaeosphaeria species, for example Phaeosphaeria nodorum; Pyrenophora species, for example Pyrenophora teres; Ramularia species, for example Ramularia collo-cygni; Rhynchosporium species, for example Rhynchosporium secalis; Septoria species, for example Septoria apii; Typhula species, for example Typhula incarnata; Venturia species, for example Venturia inaequalis; root and stem diseases caused, for example, by Corticium species, for example Corticium graminearum; Fusarium species, for example Fusarium oxysporum; Gaeumannomyces species, for example Gaeumannomyces graminis; Rhizoctonia species, for example Rhizoctonia solani; Tapesia species, for example Tapesia acuformis; Thielaviopsis species, for example Thielaviopsis basicola; ear and panicle diseases (including corn crops) caused, for example, by Alternaria species, for example Alternaria spp.; Aspergillus species, for example Aspergillus flavus; Cladosporium species, for example Cladosporium spp.; Claviceps species, for example Claviceps purpurea; Fusarium species, for example Fusarium culmorum; Gibberella species, for example Gibberella zeae; Monographella species, for example Monographella nivalis; Septoria species, for example Septoria nodorum; diseases caused by smut fungi, for example Sphacelotheca species, for example Sphacelotheca reiliana; Tilletia species, for example Tilletia caries, T. controversa; Urocystis species, for example Urocystis occulta; Ustilago species, for example Ustilago nuda, U. nuda tritici; fruit rot caused, for example, by Aspergillus species, for example Aspergillus flavus; Botrytis species, for example Botrytis cinerea; Penicillium species, for example Penicillium expansum and P. purpurogenum; Sclerotinia species, for example Sclerotinia sclerotiorum; Verticilium species, for example Verticilium alboatrum;seed- and soil-borne rot and wilt diseases, and also diseases of seedlings, caused, for example, by Fusarium species, for example Fusarium culmorum; Phytophthora species, for example Phytophthora cactorum; Pythium species, for example Pythium ultimum; Rhizoctonia species, for example Rhizoctonia solani; Sclerotium species, for example Sclerotium rolfsii; cancerous diseases, galls and witches' broom caused, for example, by Nectria species, for example Nectria galligena; wilt diseases caused, for example, by Monilinia species, for example Monilinia laxa; deformations of leaves, flowers and fruits caused, for example, by Taphrina species, for example Taphrina deformans; degenerative diseases of woody plants caused, for example, by Esca species, for example Phaemoniella clamydospora and Phaeoacremonium aleophilum and Fomitiporia mediterranea; diseases of flowers and seeds caused, for example, by Botrytis species, for example Botrytis cinerea; diseases of plant tubers caused, for example, by Rhizoctonia species, for example Rhizoctonia solani; Helminthosporium species, for example Helminthosporium solani; diseases caused by bacterial pathogens, for example Xanthomonas species, for example Xanthomonas campestris pv. oryzae; Pseudomonas species, for example Pseudomonas syringae pv. lachrymans; Erwinia species, for example Erwinia amylovora.
[0367] The Following Diseases of Soya Beans can be Controlled with Preference:
[0368] Fungal diseases on leaves, stems, pods and seeds caused, for example, by alternaria leaf spot (Alternaria spec. atrans tenuissima), Anthracnose (Colletotrichum gloeosporoides dematium var. truncatum), brown spot (Septoria glycines), cercospora leaf spot and blight (Cercospora kikuchii), choanephora leaf blight (Choanephora infundibulifera trispora (Syn.)), dactuliophora leaf spot (Dactuliophora glycines), downy mildew (Peronospora manshurica), drechslera blight (Drechslera glycini), frogeye leaf spot (Cercospora sojina), leptosphaerulina leaf spot (Leptosphaerulina trifolii), phyllostica leaf spot (Phyllosticta sojaecola), pod and stem blight (Phomopsis sojae), powdery mildew (Microsphaera diffusa), pyrenochaeta leaf spot (Pyrenochaeta glycines), rhizoctonia aerial, foliage, and web blight (Rhizoctonia solani), rust (Phakopsora pachyrhizi, Phakopsora meibomiae), scab (Sphaceloma glycines), stemphylium leaf blight (Stemphylium botryosum), target spot (Corynespora cassiicola).
[0369] Fungal diseases on roots and the stem base caused, for example, by black root rot (Calonectria crotalariae), charcoal rot (Macrophomina phaseolina), fusarium blight or wilt, root rot, and pod and collar rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), mycoleptodiscus root rot (Mycoleptodiscus terrestris), neocosmospora (Neocosmospora vasinfecta), pod and stem blight (Diaporthe phaseolorum), stem canker (Diaporthe phaseolorum var. caulivora), phytophthora rot (Phytophthora megasperma), brown stem rot (Phialophora gregata), pythium rot (Pythium aphanidermatum, Pythium irregulare, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), rhizoctonia root rot, stem decay, and damping-off (Rhizoctonia solani), sclerotinia stem decay (Sclerotinia sclerotiorum), sclerotinia southern blight (Sclerotinia rolfsii), thielaviopsis root rot (Thielaviopsis basicola).
[0370] Microorganisms capable of degrading or altering the industrial materials include, for example, bacteria, fungi, yeasts, algae and slime organisms. The active ingredients according to the invention preferably act against fungi, especially molds, wood-discoloring and wood-destroying fungi (Basidiomycetes), and against slime organisms and algae. Examples include microorganisms of the following genera: Alternaria, such as Alternaria tenuis; Aspergillus, such as Aspergillus niger; Chaetomium, such as Chaetomium globosum; Coniophora, such as Coniophora puetana; Lentinus, such as Lentinus tigrinus; Penicillium, such as Penicillium glaucum; Polyporus, such as Polyporus versicolor; Aureobasidium, such as Aureobasidium pullulans; Sclerophoma, such as Sclerophoma pityophila; Trichoderma, such as Trichoderma viride; Escherichia, such as Escherichia coli; Pseudomonas, such as Pseudomonas aeruginosa; Staphylococcus, such as Staphylococcus aureus.
[0371] In addition, the active ingredients according to the invention also have very good antimycotic activity. They have a very broad antimycotic activity spectrum, in particular against dermatophytes and yeasts, molds and diphasic fungi, (for example against Candida species, such as Candida albicans, Candida glabrata), and Epidermophyton floccosum, Aspergillus species, such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species, such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii. The enumeration of these fungi in no way constitutes a restriction of the mycotic spectrum that can be controlled, and is merely of illustrative character.
[0372] The active ingredients according to the invention can therefore be used both in medical and in non-medical applications.
[0373] If appropriate, the compounds according to the invention can, at certain concentrations or application rates, also be used as herbicides, safeners, growth regulators or agents to improve plant properties, or as microbicides, for example as fungicides, antimycotics, bactericides, viricides (including agents against viroids) or as agents against MLO (mycoplasma-like organisms) and RLO (rickettsia-like organisms). They can, as the case may be, also be used as intermediates or precursors for the synthesis of other active ingredients.
[0374] The Examples which Follow Illustrate the Invention.
[0375] Chemical Examples
[0376] 1. Synthesis of 4-(difluoromethyl)-2-methyl-3-[(methylsulfanyl)methyl]-N-(1-methyl-1H-tetrazol-5-yl)benzamide (example no. 1-107)
[0377] To an initial charge of 600 mg (2.4 mmol) of 4-(difluoromethyl)-2-methyl-3-[methylsulfanyl)methyl]benzoic acid together with 295.6 mg (2.9 mmol) of 1-methyl-1H-tetrazole-5-amine in 3 ml of pyridine at room temperature (RT) is added 0.3 ml (3.7 mmol) of oxalyl chloride. The reaction solution was stirred at RT for 12 h, then concentrated to dryness. The residue was taken up in 10 ml of water and extracted with dichloromethane. The organic phase was dried over magnesium sulfate and concentrated. The residue was taken up in acetonitrile and purified by column chromatography (HPLC, C18, gradient: acetonitrile/water (+0.5% trifluoroacetic acid), 20/80.fwdarw.100/0 in 30 min). This gave 440 mg of the target compound.
[0378] 2. Synthesis of 2-bromo-3-[methylsulfanyl)methyl]-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide (example no. 1-380)
[0379] To an initial charge of 1.46 g (4.43 mmol) of 2-(difluoromethyl)-2-methyl-3-[methylsulfanyl)methyl]benzoic acid together with 538.26 mg (5.32 mmol) of 1-methyl-1H-tetrazole-5-amine in 15 ml of acetonitrile at room temperature (RT) is added 1.8 ml of pyridine. Thereafter, 0.58 ml (6.65 mmol) of oxalyl chloride was added and the reaction mixture was stirred at RT overnight. 5 ml of water were added, and the mixture was stirred for 10 min and extracted with dichloromethane.
[0380] The organic phase was concentrated, and the residue was purified by column chromatography (HPLC, C18, gradient: acetonitrile/water (+0.5% trifluoroacetic acid), 20/80.fwdarw.100/0 in 30 min). This gave 750 mg of the target compound.
[0381] 3. Synthesis of 2-bromo-3-[methylsulfinyl)methyl]-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide (example no. 1-381)
[0382] To an initial charge of 194 mg (0.47 mmol) of 2-bromo-3-[(methylsulfanyl)methyl]-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide (example no. 1-380) in 3 ml of acetic acid at RT was added 46 mg (0.47 mmol) of a 35% aqueous hydrogen peroxide solution. The reaction solution was stirred at 50° C. for 2 h. The solvents were removed under reduced pressure, and the residue was taken up in water. The precipitate formed was filtered off and dried under high vacuum. This gave 179 mg of the target compound.
[0383] 4. Synthesis of 2-bromo-3-[(methylsulfonyl)methyl]-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide (example no. 1-382)
[0384] To an initial charge of 194 mg (0.47 mmol) of 2-bromo-3-[(methylsulfanyl)methyl]-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide (example no. 1-380) in 3 ml of acetic acid were added 137 mg (0.47 mmol) of 35% aqueous hydrogen peroxide solution and catalytic amounts of sodium tungstate. The reaction solution was stirred at 50° C. for 2 h. The solvents were removed under reduced pressure, and the residue was taken up in water. The precipitate formed was filtered off and dried under high vacuum. This gave 211 mg of the target compound.
[0385] The examples listed in the tables below were prepared analogously to the methods mentioned above or can be obtained analogously to the methods mentioned above. These compounds are very particularly preferred.
TABLE-US-00002 TABLE 1 Inventive compounds of the general formula (I) in which R.sup.x represents methyl, and the other substituents have the meanings given below.
TABLE-US-00003 TABLE 2 Inventive compounds of the general formula (I) in which R.sup.x represents ethyl, and the other substituents have the meanings given below.
TABLE-US-00004 TABLE 3 Inventive compounds of the general formula (I) in which R.sup.x represents propyl, and the other substituents have the meanings given below.
[0386] NMR data for numerous inventive compounds of the formula (I) mentioned in tables above are disclosed below for further characterization:
[0387] Ex. no. 1-37: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.79 (br s, 1H); 7.99 (d, 1H); 7.78 (d, 1H); 4.38 (s, 2H); 4.03 (s, 3H); 3.42 (s, 3H); 2.58 (s, 3H); 2.22 (s, 3H).
[0388] Ex. no. 1-38: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.83 (br s, 1H); 8.04 (d, 1H); 7.82 (d, 1H); 4.99 (d, 1H); 4.64 (d, 1H); 4.02 (s, 3H); 3.41 (s, 3H); 2.81 (s, 3H); 2.53 (s, 3H).
[0389] Ex. no. 1-39: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.85 (br s, 1H); 8.10 (d, 1H); 7.88 (d, 1H); 5.40 (br s, 2H); 4.02 (s, 3H); 3.40 (s, 3H); 3.18 (s, 3H); 2.58 (s, 3H).
[0390] Ex. no. 1-46: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.59 (br s, 1H); 7.53 (d, 1H); 7.48 (d, 1H); 3.99 (s, 3H); 2.49 (s, 3H); 2.13 (s, 3H).
[0391] Ex. no. 1-47: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.64 (br s, 1H); 7.60 (d, 1H); 7.54 (d, 1H); 4.47 (d, 1H); 4.33 (d, 1H); 3.99 (s, 3H); 2.77 (s, 3H); 2.49 (s, 3H).
[0392] Ex. no. 1-48: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.66 (br s, 1H); 7.64 (d, 1H); 7.56 (d, 11H); 4.90 (s, 2H); 3.99 (s, 3H); 3.16 (s, 3H); 2.54 (s, 3H).
[0393] Ex. no. 1-74: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.58 (br s, 1H); 7.88 (d, 1H); 7.23 (d, 1H); 4.02 (s, 2H); 3.98 (s, 3H); 2.52 (s, 3H); 2.17 (s, 3H).
[0394] Ex. no. 1-75: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.63 (br s, 1H); 7.96 (d, 1H); 7.30 (d, 1H); 4.60 (d, 1H); 4.28 (d, 1H); 3.98 (s, 3H); 2.80 (s, 3H); 2.51 (s, 3H).
[0395] Ex. no. 1-76: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.66 (br s, 1H); 7.98 (d, 1H); 7.33 (d, 1H); 4.94 (s, 2H); 3.99 (s, 3H); 3.17 (s, 3H); 2.57 (s, 3H).
[0396] Ex. no. 1-83:.sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ=8.72 (br s, 1H); 7.68 (d, 1H); 7.59 (d, 1H); 4.14 (s, 3H); 3.93 (s, 2H); 2.66 (s, 3H); 2.19 (s, 3H).
[0397] Ex. no. 1-84: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.79 (br s, 1H); 7.80 (d, 1H); 7.76 (d, 1H); 4.54 (d, 1H); 4.21 (d, 1H); 4.01 (s, 3H); 2.81 (s, 3H); 2.55 (s, 3H).
[0398] Ex. no. 1-85: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.82 (br s, 1H); 7.82 (s, 2H); 4.91 (br s, 2H); 4.02 (s, 3H); 3.19 (s, 3H); 2.58 (s, 3H).
[0399] Ex. no. 1-86: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ=10.64 (br s, 1H); 7.71 (d, 1H); 7.67 (d, 1H); 4.12 (s, 3H); 3.95 (s, 2H); 2.67 (m, 2H); 2.67 (s, 3H); 1.31 (t, 3H).
[0400] Ex. no. 1-88: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.82 (br s, 1H); 7.82 (s, 2H); 4.84 (br s, 2H); 4.02 (s, 3H); 3.33 (m, 2H); 2.58 (s, 3H); 1.33 (t, 3H).
[0401] Ex. no. 1-107: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.63 (br s, 1H); 7.65 (d, 1H); 7.58 (d, 1H); 7.34 (t, 1H); 4.00 (s, 3H); 3.96 (s, 2H); 2.49 (s, 3H); 2.15 (s, 3H).
[0402] Ex. no. 1-108: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.69 (br s, 1H); 7.72 (d, 1H); 7.65 (d, 1H); 7.38 (t, 1H); 4.45 (d, 1H); 4.36 (d, 1H); 2.80 (s, 3H); 2.46 (s, 3H).
[0403] Ex. no. 1-109: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.71 (br s, 1H); 7.77 (d, 1H); 7.69 (d, 1H); 7.33 (t, 1H); 4.94 (br s, 2H); 4.00 (s, 3H); 3.25 (s, 3H); 2.52 (s, 3H).
[0404] Ex. no. 1-134: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ=10.02 (br s, 1H); 8.07 (d, 1H); 7.64 (d, 1H); 4.12 (s, 3H); 4.10 (s, 3H); 3.96 (s, 2H); 2.25 (s, 3H).
[0405] Ex. no. 1-135: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ=10.25 (br s, 1H); 8.08 (d, 1H); 7.69 (d, 1H); 4.45 (d, 1H); 4.18 (d, 1H); 4.09 (s, 3H); 4.06 (s, 3H); 2.76 (s, 3H).
[0406] Ex. no. 1-161: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.78 (br s, 1H); 7.91 (d, 1H); 7.76 (d, 1H); 4.19 (s, 2H); 4.06 (s, 1H); 2.46 (s, 3H); 2.22 (s, 3H).
[0407] Ex. no. 1-162: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.83 (br s, 1H); 7.99 (d, 1H); 7.84 (d, 1H); 4.64 (d, 1H); 4.59 (d, 1H); 4.06 (s, 3H); 2.79 (s, 3H); 2.40 (s, 3H).
[0408] Ex. no. 1-163: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.87 (br s, 1H); 8.02 (d, 1H); 7.90 (d, 1H); 5.13 (br s, 2H); 4.06 (s, 3H); 3.22 (s, 3H); 2.38 (s, 3H).
[0409] Ex. no. 1-170: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.71 (br s, 1H); 7.79 (d, 1H); 7.70 (d, 1H); 7.39 (t, 1H); 4.27 (s, 2H); 4.05 (s, 3H); 2.42 (s, 3H); 2.17 (s, 3H).
[0410] Ex. no. 1-171: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.76 (br s, 1H); 7.85 (d, 1H); 7.79 (d, 1H); 7.41 (t, 1H); 4.72 (d, 1H); 4.66 (d, 1H); 4.06 (s, 3H); 2.79 (s, 3H); 2.38 (s, 3H).
[0411] Ex. no. 1-172: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.77 (br s, 1H); 7.89 (d, 1H); 7.83 (d, 1H); 7.38 (t, 1H); 5.25 (br s, 2H); 4.05 (s, 3H); 3.21 (s, 3H); 2.38 (s, 3H).
[0412] Ex. no. 1-182: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.78 (br s, 1H); 7.91 (d, 1H); 7.76 (d, 1H); 4.23 (s, 2H); 4.06 (s, 3H); 2.94 (q, 2H); 2.71 (q, 2H); 1.26 (t, 3H); 1.13 (t, 3H).
[0413] Ex. no. 1-191: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.69 (br s, 1H); 7.78 (d, 1H); 7.69 (d, 1H); 7.38 (t, 1H); 4.32 (s, 2H); 4.05 (s, 3H); 2.92 (q, 2H); 2.66 (q, 2H); 1.26 (t, 3H); 1.13 (t, 3H).
[0414] Ex. no. 1-199: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=12.08 (br s, 1H); 8.38 (d, 1H); 8.15 (d, 1H); 6.18 (d, 1H); 4.88 (d, 1H); 4.04 (s, 1H); 3.64 (s, 3H); 3.27 (s, 3H).
[0415] Ex. no. 1-229: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.95 (br s, 1H); 8.19 (d, 1H); 8.02 (d, 1H); 7.42 (t, 1H); 3.98 (s, 3H); 3.82 (m, 2H); 3.43 (q, 2H); 1.33 (t, 3H); 1.27 (t, 3H).
[0416] Ex. no. 1-242: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=9.09 (br s, 1H); 8.14 (t, 1H); 7.67 (d, 1H); 4.09 (s, 3H); 3.96 (s, 2H); 2.22 (s, 3H).
[0417] Ex. no. 1-244: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.95 (br s, 1H); 8.05 (t, 1H); 7.87 (d, 1H); 4.81 (s, 2H); 3.99 (s, 3H); 3.22 (s, 3H).
[0418] Ex. no. 1-278: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ=8.18 (d, 1H); 7.69 (d, 1H); 4.53 (s, 2H); 4.45 (s, 3H); 3.38 (s, 3H); 2.28 (s, 3H).
[0419] Ex. no. 1-280: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=12.06 (br s, 1H); 8.24 (d, 1H); 8.06 (d, 1H); 5.43 (br s, 2H); 4.03 (s, 3H); 3.45 (s, 3H); 3.22 (s, 3H).
[0420] Ex. no. 1-287: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=7.51 (d, 1H); 7.26 (d, 1H); 3.95 (s, 2H); 2.45 (s, 3H); 2.11 (s, 3H).
[0421] Ex. no. 1-288: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.74 (br s, 1H); 7.58 (d, 1H); 7.38 (d, 1H); 4.41 (d, 1H); 4.32 (d, 1H); 3.99 (s, 3H); 2.77 (s, 3H).
[0422] Ex. no. 1-289: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.75 (br s, 1H); 7.62 (d, 1H); 7.41 (d, 1H); 4.85 (s, 2H); 3.99 (s, 3H); 3.15 (s, 3H); 2.54 (s, 3H).
[0423] Ex. no. 1-296: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ=9.38 (br s, 1H); 7.76 (d, 1H); 7.69 (d, 1H); 4.14 (s, 3H); 4.05 (s, 2H); 2.24 (s, 3H).
[0424] Ex. no. 1-297: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=12.02 (br s, 1H); 7.96 (m, 2H); 4.48 (d, 1H); 4.42 (d, 1H); 4.03 (s, 3H); 2.81 (s, 3H).
[0425] Ex. no. 1-298: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=12.04 (br s, 1H); 8.00 (s, 2H); 4.98 (br s, 2H); 4.03 (s, 3H); 3.24 (s, 3H).
[0426] Ex. no. 1-299: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.97 (br s, 1H); 7.90 (d, 1H); 7.86 (d, 1H); 4.04 (s, 2H); 4.02 (s, 3H); 2.72 (q, 2H); 1.25 (t, 3H).
[0427] Ex. no. 1-300: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=12.02 (br s, 1H); 7.98 (d, 1H); 7.94 (d, 1H); 4.43 (d, 1H); 4.38 (d, 1H); 4.02 (s, 3H); 3.08 (m, 1H); 2.94 (m, 1H); 1.29 (t, 3H).
[0428] Ex. no. 1-301: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ=9.81 (br s, 1H); 7.85 (d, 1H); 7.80 (d, 1H); 4.85 (s, 2H); 4.12 (s, 3H); 3.21 (q, 2H); 1.50 (t, 3H).
[0429] Ex. no. 1-302: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.97 (br s, 1H); 7.90 (d, 1H); 7.86 (d, 1H); 4.13 (s, 2H); 4.02 (s, 3H); 2.10 (m, 1H); 0.89 (m, 2H); 0.49 (m, 2H).
[0430] Ex. no. 1-303: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=12.02 (br s, 1H); 7.98 (d, 1H); 7.94 (d, 1H); 4.55 (d, 1H); 4.48 (d, 1H); 4.02 (s, 3H); 2.67 (m, 1H); 0.99 (m, 2H); 0.68 (m, 2H).
[0431] Ex. no. 1-304: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=12.04 (br s, 1H); 8.00 (s, 2H); 5.00 (s, 2H); 4.03 (s, 3H); 2.96 (m, 1H); 1.11 (m, 2H); 1.05 (m, 2H).
[0432] Ex. no. 1-305: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.97 (br s, 1H); 7.92 (d, 1H); 7.88 (d, 1H); 4.11 (s, 2H); 4.02 (s, 3H); 3.57 (t, 2H); 3.28 (s, 3H); 2.88 (t, 2H).
[0433] Ex. no. 1-306: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=12.01 (br s, 1H); 7.97 (d, 1H); 7.94 (d, 1H); 4.55 (d, 1H); 4.46 (d, 1H); 4.02 (s, 3H); 3.81 (m, 1H); 3.75 (m, 1H); 3.33 (m, 1H); 3.31 (s, 3H); 3.17 (m, 1H).
[0434] Ex. no. 1-307: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=12.05 (br s, 1H); 7.99 (s, 2H); 5.00 (br s, 2H); 4.03 (s, 3H); 3.80 (t, 2H); 3.63 (t, 2H); 3.35 (s, 3H).
[0435] Ex. no. 1-308: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.96 (br s, 1H); 7.90 (d, 1H); 7.86 (d, 1H); 5.87 (m, 1H); 5.26 (d, 1H); 5.85 (d, 1H); 4.02 (s, 3H); 3.96 (s, 2H); 3.38 (d, 2H).
[0436] Ex. no. 1-311: H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.99 (br s, 1H); 7.93 (m, 2H); 4.26 (s, 2H); 4.03 (s, 3H); 3.75 (q, 2H).
[0437] Ex. no. 1-312: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=12.03 (br s, 1H); 8.00 (s, 2H); 4.80 (d, 1H); 4.61 (d, 1H); 4.49 (m, 1H); 4.29 (m, 1H); 4.03 (s, 3H).
[0438] Ex. no. 1-313: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=12.05 (br s, 1H); 8.03 (m, 2H); 5.13 (br s, 2H); 4.98 (q, 2H); 4.03 (s, 3H).
[0439] Ex. no. 1-314: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.97 (br s, 1H); 7.90 (d, 1H); 7.85 (d, 1H); 4.10 (s, 2H); 4.02 (s, 3H); 2.67 (d, 2H); 1.02 (m, 1H); 0.55 (m, 2H); 0.24 (m, 2H).
[0440] Ex. no. 1-315: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=12.02 (br s, 1H); 7.97 (d, 1H); 7.94 (d, 1H); 4.50 (d, 1H); 4.44 (d, 1H); 4.02 (s, 3H); 3.00 (m, 2H); 1.14 (m, 1H); 0.65 (m, 2H); 0.47 (m, 1H); 0.38 (m, 1H).
[0441] Ex. no. 1-316: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=12.05 (br s, 1H); 8.00 (s, 2H); 4.94 (br s, 2H); 4.03 (s, 3H); 3.34 (d, 2H); 1.18 (m, 1H); 0.69 (m, 2H); 0.48 (m, 2H).
[0442] Ex. no. 1-317: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.96 (br s, 1H); 7.89 (d, 1H); 7.85 (d, 1H); 4.04 (s, 2H); 4.02 (s, 3H); 3.18 (m, 1H); 1.29 (d, 6H).
[0443] Ex. no. 1-320: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.90 (br s, 1H); 7.80 (d, 1H); 7.75 (d, 1H); 7.38 (t, 1H); 4.07 (s, 2H); 4.01 (s, 3H); 2.14 (s, 3H).
[0444] Ex. no. 1-321: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.93 (br s, 1H); 7.90 (d, 1H); 7.82 (d, 1H); 7.39 (t, 1H); 4.54 (s, 2H); 4.02 (s, 3H); 2.79 (s, 3H).
[0445] Ex. no. 1-322: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.94 (br s, 1H); 7.94 (d, 1H); 7.86 (d, 1H); 7.35 (t, 1H); 5.07 (s, 2H); 4.02 (s, 3H); 3.24 (s, 3H).
[0446] Ex. no. 1-323: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.89 (br s, 1H); 7.79 (d, 1H); 7.74 (d, 1H); 7.36 (t, 1H); 4.09 (s, 2H); 4.01 (s, 3H); 2.65 (q, 2H); 1.23 (t, 3H).
[0447] Ex. no. 1-324: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.97 (br s, 1H); 7.89 (d, 1H); 7.82 (d, 1H); 7.38 (t, 1H); 4.49 (s, 2H); 4.02 (s, 3H); 3.09 (m, 1H); 2.97 (m, 1H); 1.29 (t, 3H).
[0448] Ex. no. 1-325: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.95 (br s, 1H); 7.94 (d, 1H); 7.86 (d, 1H); 7.32 (t, 1H); 5.01 (s, 2H); 4.02 (s, 3H); 3.38 (q, 2H); 1.33 (t, 3H).
[0449] Ex. no. 1-326: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.89 (br s, 1H); 7.79 (d, 1H); 7.74 (d, 1H); 7.39 (t, 1H); 4.16 (s, 2H); 4.01 (s, 3H); 2.01 (m, 1H); 0.84 (m, 2H); 0.44 (m, 2H).
[0450] Ex. no. 1-327: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.92 (br s, 1H); 7.87 (d, 1H); 7.80 (d, 1H); 7.37 (t, 1H); 4.59 (q, 2H); 4.01 (s, 3H); 2.61 (m, 1H); 0.96 (m, 3H); 0.67 (m, 1H).
[0451] Ex. no. 1-328: .sup.H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.92 (br s, 1H); 7.94 (d, 1H); 7.85 (d, 1H); 7.36 (t, 1H); 5.08 (s, 2H); 4.02 (s, 3H); 2.92 (m, 1H); 1.09 (m, 2H); 1.02 (m, 2H).
[0452] Ex. no. 1-335: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.90 (br s, 1H); 7.84 (d, 1H); 7.76 (d, 1H); 7.35 (t, 1H); 4.28 (s, 2H); 4.02 (s, 3H); 3.71 (q, 2H).
[0453] Ex. no. 1-336: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.56 (br s, 1H); 7.93 (d, 1H); 7.84 (d, 1H); 7.36 (t, 1H); 4.89 (d, 1H); 4.67 (d, 1H); 4.45 (m, 1H); 4.34 (m, 1H); 4.02 (s, 3H).
[0454] Ex. no. 1-337: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.97 (br s, 1H); 7.99 (d, 1H); 7.89 (d, 1H); 7.28 (t, 1H); 5.20 (s, 2H); 5.022 (q, 2H); 4.02 (s, 3H).
[0455] Ex. no. 1-338: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.91 (br s, 1H); 7.79 (d, 1H); 7.74 (d, 1H); 7.37 (t, 1H); 4.14 (s, 2H); 4.02 (s, 3H); 2.62 (d, 2H); 1.01 (m, 1H); 0.54 (m, 2H); 0.22 (m, 2H).
[0456] Ex. no. 1-339: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.94 (br s, 1H); 7.88 (d, 1H); 7.81 (d, 1H); 7.38 (t, 1H); 4.55 (d, 1H); 4.50 (d, 1H); 4.02 (s, 3H); 3.02 (m, 2H); 1.12 (m, 1H); 0.65 (m, 2H); 0.44 (m, 1H); 0.39 (m, 1H).
[0457] Ex. no. 1-340: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.96 (br s, 1H); 7.94 (d, 1H); 7.86 (d, 1H); 7.31 (t, 1H); 5.01 (s, 2H); 4.02 (s, 3H); 3.38 (d, 2H); 1.19 (m, 1H); 0.70 (m, 2H); 0.48 (m, 2H).
[0458] Ex. no. 1-353: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.84 (br s, 1H); 7.82 (d, 1H); 7.57 (d, 1H); 4.07 (s, 2H); 4.00 (s, 3H); 2.17 (s, 3H).
[0459] Ex. no. 1-354: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.88 (br s, 1H); 7.88 (d, 1H); 7.65 (d, 1H); 4.56 (d, 1H); 4.48 (d, 1H); 4.00 (s, 3H); 2.78 (s, 3H).
[0460] Ex. no. 1-355: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.91 (br s, 1H); 7.90 (d, 1H); 7.69 (d, 1H); 4.97 (s, 2H); 4.00 (s, 3H); 3.19 (s, 3H).
[0461] Ex. no. 1-356: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.86 (br s, 1H); 7.81 (d, 1H); 7.57 (d, 1H); 4.09 (s, 2H); 4.00 (s, 3H); 2.66 (q, 2H); 1.25 (t, 3H).
[0462] Ex. no. 1-357: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.90 (br s, 1H); 7.87 (d, 1H); 7.65 (d, 1H); 4.51 (d, 1H); 4.43 (d, 1H); 4.00 (s, 3H); 3.02 (m, 1H); 2.92 (m, 1H); 1.30 (t, 3H).
[0463] Ex. no. 1-358: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.91 (br s, 1H); 7.90 (d, 1H); 7.69 (d, 1H); 4.92 (br s, 2H); 4.00 (s, 3H); 3.32 (q, 2H); 1.33 (t, 3H). Ex. no. 1-362: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.81 (br s, 1H); 8.03 (d, 1H); 7.35 (d, 1H); 4.10 (s, 2H); 3.99 (s, 3H); 2.19 (s, 3H).
[0464] Ex. no. 1-363: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.85 (br s, 1H); 8.09 (d, 1H); 7.43 (d, 1H); 4.59 (d, 1H); 4.52 (d, 1H); 3.99 (s, 3H); 2.79 (s, 3H).
[0465] Ex. no. 1-364: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.87 (br s, 1H); 8.11 (d, 1H); 4.99 (s, 2H); 4.00 (s, 3H); 3.19 (s, 3H).
[0466] Ex. no. 1-380: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=12.00 (br s, 1H); 7.94 (d, 1H); 7.81 (d, 1H); 4.05 (s, 5H); 2.24 (s, 3H).
[0467] Ex. no. 1-381: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.94 (br s, 1H); 8.00 (d, 1H); 7.88 (d, 1H); 4.48 (q, 2H); 4.04 (s, 3H); 2.81 (s, 3H).
[0468] Ex. no. 1-382: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.99 (br s, 1H); 8.01 (d, 1H); 7.91 (d, 1H); 5.01 (br s, 2H); 4.03 (s, 3H); 3.25 (s, 3H).
[0469] Ex. no. 1-383: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.96 (br s, 1H); 7.93 (d, 1H); 7.80 (d, 1H); 4.07 (s, 2H); 4.04 (s, 3H); 2.73 (q, 2H); 1.26 (t, 3H).
[0470] Ex. no. 1-384: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=12.02 (br s, 1H); 8.00 (d, 1H); 7.89 (d, 1H); 4.46 (d, 1H); 4.40 (d, 1H); 4.04 (s, 3H); 3.09 (m, 1H); 2.97 (m, 1H); 1.30 (t, 3H).
[0471] Ex. no. 1-385: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=12.03 (br s, 1H); 7.98 (d, 1H); 7.87 (d, 1H); 4.94 (br s, 2H); 3.99 (s, 3H); 3.36 (q, 2H); 1.34 (t, 3H).
[0472] Ex. no. 1-404: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.88 (br s, 1H); 7.78 (d, 11H); 7.74 (d, 1H); 7.38 (t, 11H); 4.09 (s, 2H); 4.02 (s, 3H); 2.16 (s, 3H).
[0473] Ex. no. 1-405: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.93 (br s, 1H); 7.84 (br s, 2H); 7.40 (t,1H); 4.58 (d, 1H); 4.52 (d, 1H); 4.04 (s, 3H); 2.81 (s, 3H).
[0474] Ex. no. 1-406: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.93 (br s, 1H); 7.88 (br s, 2H); 7.36 (t, 1H); 5.09 (br s, 2H); 4.04 (s, 3H); 3.24 (s, 3H).
[0475] Ex. no. 1-407: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.88 (br s, 1H); 7.77 (d, 1H); 7.73 (d, 1H); 7.36 (t, 1H), 4.10 (s, 2H); 4.03 (s, 3H); 2.67 (q, 2H); 1.24 (t, 3H).
[0476] Ex. no. 1-408: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.93 (br s, 1H); 7.84 (br s, 2H); 7.37 (t, 1H); 4.55 (d, 1H); 4.48 (d, 1H); 4.04 (s, 3H); 3.09 (m, 1H); 2.99 (m, 1H); 1.30 (t, 3H).
[0477] Ex. no. 1-409: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.96 (br s, 1H); 7.88 (s, 2H); 7.33 (t, 1H); 5.04 (s, 2H); 4.04 (s, 3H); 3.38 (q, 2H); 1.34 (t, 3H).
[0478] Ex. no. 1-487: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.67 (br s, 1H); 7.67 (d, 1H); 7.60 (d, 1H); 7.36 (t, 1H); 4.00 (s, 3H); 3.95 (s, 2H); 2.89 (q, 2H); 2.19 (s, 3H); 1.22 (t, 3H).
[0479] Ex. no. 1-490: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.76 (br s, 1H); 7.73 (m, 2H); 4.01 (s, 3H); 3.95 (s, 2H); 2.98 (q, 2H); 2.70 (q, 2H); 1.26 (m, 6H).
[0480] Ex. no. 1-493: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.76 (br s, 1H); 7.73 (m, 2H); 4.01 (s, 2H); 4.01 (s, 3H); 2.97 (q, 2H); 2.10 (m, 1H); 1.24 (t, 3H); 0.90 (m, 2H); 0.51 (m, 2H).
[0481] Ex. no. 1-494: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.83 (br s, 1H); 7.83 (d, 1H); 7.79 (d, 1H); 4.48 (d, 1H); 4.29 (d, 1H); 3.20 (m, 1H); 2.82 (m, 1H); 2.72 (m, 1H); 1.18 (t, 3H); 1.03 (m, 3H); 0.69 (m, 1H).
[0482] Ex. no. 1-495: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.89 (br s, 1H); 7.84 (m, 2H); 4.88 (br s, 2H); 4.02 (s, 3H); 3.07 (br s, 1H); 2.95 (m, 1H); 1.16 (t, 3H); 1.10 (m, 2H); 1.02 (m, 2H).
[0483] Ex. no. 1-497: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.72 (br s, 1H); 7.74 (d, 1H); 7.66 (d, 1H); 7.41 (t, 1H); 4.41 (d, 1H); 4.33 (d, 1H); 4.01 (s, 3H); 2.98 (m, 1H); 2.48 (s, 3H); 2.81 (m, 1H); 1.17 (t, 3H).
[0484] Ex. no. 1-498: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.75 (br s, 1H); 7.79 (d, 1H); 7.70 (d, 1H); 7.34 (t, 1H); 4.89 (s, 2H); 4.01 (s, 3H); 3.29 (s, 3H); 2.93 (br q, 2H); 1.15 (t, 3H).
[0485] Ex. no. 1-514: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.69 (br s, 1H); 7.75 (d, 1H); 7.64 (d, 1H); 4.18 (s, 2H); 4.04 (s, 3H); 2.29 (m, 1H); 2.18 (s, 3H); 1.11 (m, 2H); 0.64 (m, 2H).
[0486] Ex. no. 1-515: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.75 (br s, 1H); 7.83 (d, 1H); 7.73 (d, 1H); 4.70 (d, 1H); 4.42 (d, 2H); 4.04 (s, 3H); 2.78 (s, 3H); 2.25 (m, 1H); 1.15 (m, 2H); 0.61 (m, 2H).
[0487] Ex. no. 1-516: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.79 (br s, 1H); 7.87 (d, 1H); 7.80 (m, 1H); 5.32 (br s, 1H); 4.79 (br s, 1H); 4.04 (s, 3H); 3.19 (s, 3H); 2.32 (m, 1H); 1.17 (br s, 2H); 0.58 (br s, 2H).
[0488] Ex. no. 1-517: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.70 (br s, 1H); 7.77 (d, 1H); 7.65 (d, 1H); 4.22 (s, 2H); 4.04 (s, 3H); 2.69 (q, 2H); 2.28 (m, 1H); 1.26 (t, 3H); 1.11 (m, 2H); 0.66 (d, 2H).
[0489] Ex. no. 1-518: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.75 (br s, 1H); 7.83 (d, 1H); 7.73 (d, 1H); 4.68 (d, 1H); 4.37 (d, 1H); 4.04 (s, 3H); 3.03 (m, 1H); 2.92 (m, 1H); 2.25 (m, 1H); 1.29 (t, 3H); 1.11 (m, 2H); 0.61 (m, 2H).
[0490] Ex. no. 1-519: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.77 (br s, 1H); 7.86 (d, 1H); 7.80 (d, 1H); 5.28 (br s, 1H); 4.70 (br s, 1H); 4.04 (s, 3H); 3.32 (q, 2H); 2.34 (m, 1H); 1.32 (t, 3H); 1.14 (br s, 2H); 0.58 (br s, 2H).
[0491] Ex. no. 1-523: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.60 (br s, 1H); 7.38 (t, 1H); 4.20 (s, 2H); 4.03 (s, 3H); 2.17 (s, 3H); 2.16 (m, 1H); 1.06 (m, 2H); 0.64 (m, 2H).
[0492] Ex. no. 1-524: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.66 (br s, 1H); 7.68 (br s, 2H); 7.42 (t, 1H); 4.60 (s, 2H); 4.03 (s, 3H); 2.80 (s, 3H); 2.09 (m, 1H); 1.09 (m, 2H); 0.59 (m, 2H).
[0493] Ex. no. 1-525: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.70 (br s, 1H); 7.73 (br s, 1H); 7.35 (t, 1H); 5.11 (br s, 2H); 4.03 (s, 3H); 3.25 (s, 3H); 2.23 (m, 1H); 1.13 (m, 2H); 0.57 (m, 2H).
[0494] Ex. no. 1-552: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=12.05 (br s, 1H); 8.37 (d, 1H); 8.14 (br s, 1H); 5.01 (d, 1H); 4.85 (d, 1H); 4.01 (s, 3H); 3.21 (s, 3H).
[0495] Ex. no. 1-559: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ=10.71 (br s, 1H); 7.58 (d, 1H); 7.50 (d, 1H); 4.11 (s, 3H); 4.09 (s, 2H); 2.19 (s, 3H).
[0496] Ex. no. 1-561: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.91 (br s, 1H); 7.90 (d, 1H); 7.75 (d, 1H); 4.94 (s, 2H); 4.00 (s, 3H); 3.19 (s, 3H).
[0497] Ex. no. 1-568: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=12.02 (br s, 1H); 7.98 (d, 1H); 7.94 (d, 1H); 4.48 (d, 1H); 4.42 (d, 1H); 4.03 (s, 3H); 2.81 (s, 3H).
[0498] Ex. no. 1-569: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=12.02 (br s, 1H); 7.98 (d, 1H); 7.94 (d, 1H); 4.49 (d, 1H); 4.42 (d, 1H); 4.03 (s, 3H); 2.81 (s, 3H).
[0499] Ex. no. 1-570: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ=10.09 (br s, 1H); 7.97 (d, 1H); 7.41 (d, 1H); 4.10 (s, 3H); 4.08 (s, 3H); 3.95 (s, 2H); 2.22 (s, 3H).
[0500] Ex. no. 1-571: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ=8.01 (d, 1H); 7.46 (d, 1H); 4.41 (d, 1H); 4.24 (d, 1H); 4.09 (s, 3H); 4.07 (s, 3H); 2.76 (s, 3H).
[0501] Ex. no. 1-572: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ=9.95 (br s, 1H); 8.03 (d, 1H); 7.49 (d, 1H); 4.68 (s, 2H); 4.09 (s, 3H); 4.07 (s, 3H); 3.03 (s, 3H).
[0502] Ex. no. 2-37: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.67 (br s, 1H); 7.98 (d, 1H); 7.75 (d, 1H); 4.36 (m, 4H); 3.40 (s, 3H); 2.56 (s, 3H); 2.20 (s, 3H); 1.48 (t, 3H).
[0503] Ex. no. 2-39: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.75 (br s, 1H); 8.11 (d, 1H); 7.87 (d, 1H); 5.41 (br s, 2H); 4.37 (q, 2H); 3.40 (s, 3H); 3.19 (s, 3H); 2.58 (s, 3H); 1.48 (t, 3H).
[0504] Ex. no. 2-46: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.49 (br s, 1H); 7.52 (d, 1H); 7.48 (d, 1H); 4.34 (q, 2H); 3.98 (s, 2H); 2.49 (s, 3H); 2.13 (s, 3H); 1.47 (t, 3H).
[0505] Ex. no. 2-47: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.53 (br s, 1H); 7.59 (d, 1H); 7.54 (d, 1H); 4.47 (d, 1H); 4.34 (m, 3H); 2.77 (s, 3H); 2.50 (s, 3H); 1.47 (t, 3H).
[0506] Ex. no. 2-48:'H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.56 (br s, 1H); 7.63 (d, 1H); 7.56 (d, 1H); 4.90 (s, 2H); 4.34 (q, 2H); 3.16 (s, 3H); 2.54 (s, 3H); 1.47 (t, 3H).
[0507] Ex. no. 2-74: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.48 (br s, 1H); 7.89 (d, 1H); 7.22 (d, 1H); 4.33 (q, 2H); 4.03 (s, 2H); 2.52 (s, 3H); 2.17 (s, 3H); 1.46 (t, 3H).
[0508] Ex. no. 2-75: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.53 (br s, 1H); 7.96 (d, 1H); 7.28 (d, 1H); 4.60 (d, 1H); 4.33 (q, 2H); 4.28 (d, 1H); 2.80 (s, 3H); 2.51 (s, 3H); 1.46 (t, 3H).
[0509] Ex. no. 2-76: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.55 (br s, 1H); 7.98 (d, 1H); 7.32 (d, 1H); 4.94 (br s, 2H); 4.33 (q, 2H); 3.17 (s, 3H); 2.57 (s, 3H); 1.47 (t, 3H).
[0510] Ex. no. 2-86: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ=10.62 (br s, 1H); 7.67 (m, 2H); 4.50 (q, 2H); 3.94 (s, 2H); 2.67 (s, 3H); 2.65 (m, 2H); 1.63 (t, 3H); 1.31 (t, 3H).
[0511] Ex. no. 2-88: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.72 (br s, 1H); 7.82 (m, 2H); 4.84 (br s, 2H); 4.36 (q, 2H); 3.33 (m, 2H); 2.58 (s, 3H); 1.48 (t, 3H); 1.33 (t, 3H).
[0512] Ex. no. 2-107: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.55 (br s, 1H); 7.64 (d, 1H); 7.59 (d, 1H); 7.34 (t, 1H); 4.35 (q, 2H); 3.96 (s, 3H); 2.49 (s, 3H); 2.15 (s, 3H); 1.48 (t, 3H).
[0513] Ex. no. 2-108: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.59 (br s, 1H); 7.71 (d, 1H); 7.65 (d, 1H); 7.38 (t, 1H); 4.45 (d, 1H); 4.36 (m, 3H); 2.80 (s, 3H); 2.46 (s, 3H); 1.48 (t, 3H).
[0514] Ex. no. 2-109: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.60 (br s, 1H); 7.76 (d, 1H); 7.69 (d, 1H); 7.33 (t, 1H); 4.94 (s, 2H); 4.35 (q, 2H); 3.25 (s, 3H); 2.52 (s, 3H); 1.48 (t, 3H).
[0515] Ex. no. 2-134: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ=9.99 (br s, 1H); 8.07 (d, 1H); 7.64 (d, 1H); 4.44 (q, 2H); 4.12 (s, 3H); 3.96 (s, 2H); 2.25 (s, 3H); 1.62 (t, 3H).
[0516] Ex. no. 2-136: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ=9.93 (br s, 1H); 8.13 (d, 1H); 7.71 (d, 1H); 4.71 (s, 2H); 4.43 (q, 2H); 3.98 (s, 3H); 3.06 (s, 3H); 1.63 (t, 3H).
[0517] Ex. no. 2-161: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.67 (br s, 1H); 7.91 (d, 1H); 7.75 (d, 1H); 4.43 (q, 2H); 4.19 (s, 2H); 2.46 (s, 3H); 2.22 (s, 3H); 1.50 (t, 3H).
[0518] Ex. no. 2-162: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.73 (br s, 1H); 7.99 (d, 1H); 7.83 (d, 1H); 4.64 (d, 1H); 4.56 (d, 1H); 4.44 (q, 2H); 2.79 (s, 3H); 2.40 (s, 3H); 1.50 (t, 3H).
[0519] Ex. no. 2-163: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.76 (br s, 1H); 8.02 (d, 1H); 7.89 (d, 1H); 5.14 (br s, 2H); 4.44 (q, 2H); 3.23 (s, 3H); 2.39 (s, 3H); 1.50 (t, 3H).
[0520] Ex. no. 2-170: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.60 (br s, 1H); 7.79 (d, 1H); 7.68 (d, 1H); 7.39 (t, 1H); 4.43 (q, 2H); 4.27 (s, 2H); 2.43 (s, 3H); 2.17 (s, 3H); 1.49 (t, 3H).
[0521] Ex. no. 2-171: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.65 (br s, 1H); 7.86 (d, 1H); 7.78 (d, 1H); 7.41 (t, 1H); 4.72 (d, 1H); 4.66 (d, 1H); 4.44 (q, 2H); 2.80 (s, 3H); 2.38 (s, 3H); 1.50 (t, 3H).
[0522] Ex. no. 2-172: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.67 (br s, 1H); 7.90 (d, 1H); 7.83 (d, 1H); 7.38 (t, 1H); 5.25 (br s, 2H); 4.43 (q, 2H); 3.22 (s, 3H); 2.38 (s, 3H); 1.50 (t, 3H).
[0523] Ex. no. 2-278: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ=10.5 (br s, 1H); 8.15 (d, 1H); 7.69 (d, 1H); 4.52 (m, 4H); 3.38 (s, 3H); 2.28 (s, 3H); 1.65 (t, 3H).
[0524] Ex. no. 2-280: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ=10.61 (br s, 1H); 8.17 (d, 1H); 7.85 (d, 1H); 4.46 (q, 2H); 3.34 (s, 3H); 3.14 (s, 3H); 1.62 (t, 3H).
[0525] Ex. no. 2-287: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.59 (br s, 1H); 7.49 (d, 1H); 7.34 (d, 1H); 4.35 (q, 2H); 3.96 (d, 2H); 2.48 (s, 3H); 2.13 (s, 3H); 1.47 (t, 3H).
[0526] Ex. no. 2-288: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.65 (br s, 1H); 7.56 (d, 1H); 7.38 (d, 1H); 4.36 (m, 4H); 2.77 (s, 3H); 1.47 (t, 3H).
[0527] Ex. no. 2-289: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.65 (br s, 1H); 7.61 (d, 1H); 7.41 (d, 1H); 4.85 (s, 3H); 4.36 (q, 2H); 3.15 (s, 3H); 2.54 (s, 3H); 1.47 (t, 3H).
[0528] Ex. no. 2-296: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ=10.10 (br s, 1H); 7.75 (d, 1H); 7.68 (d, 1H); 4.50 (q, 2H); 4.05 (s, 3H); 2.22 (s, 3H); 1.64 (t, 3H).
[0529] Ex. no. 2-297: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.92 (br s, 1H); 7.97 (d, 1H); 7.93 (d, 1H); 4.48 (d, 1H); 4.43 (d, 1H); 4.38 (q, 2H); 2.81 (s, 3H); 1.48 (t, 3H).
[0530] Ex. no. 2-298: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.94 (br s, 1H); 8.00 (s, 2H); 4.98 (br s, 2H); 4.39 (q, 2H); 3.24 (s, 3H); 1.49 (t, 3H).
[0531] Ex. no. 2-299: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.88 (br s, 1H); 7.90 (d, 1H); 7.85 (d, 1H); 4.38 (q, 2H); 4.04 (s, 2H); 2.72 (q, 2H); 1.48 (t, 3H); 1.25 (t, 3H).
[0532] Ex. no. 2-300: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.92 (br s, 1H); 7.97 (d, 1H); 7.93 (d, 1H); 4.40 (m, 4H); 3.09 (m, 1H); 2.95 (m, 1H); 1.48 (t, 3H); 1.30 (t, 3H).
[0533] Ex. no. 2-301: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ=9.91 (br s, 1H); 7.83 (d, 1H); 7.80 (d, 1H); 4.84 (s, 2H); 4.47 (q, 2H); 3.21 (q, 2H); 1.63 (t, 3H); 1.49 (t, 3H).
[0534] Ex. no. 2-302: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.88 (br s, 1H); 7.90 (d, 1H); 7.85 (d, 1H); 4.38 (q, 2H); 4.13 (s, 2H); 2.10 (m, 1H); 1.48 (t, 3H); 0.88 (m, 2H); 0.49 (m, 2H).
[0535] Ex. no. 2-303: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.92 (br s, 1H); 7.98 (d, 1H); 7.93 (d, 1H); 4.55 (d, 1H); 4.48 (d, 1H); 4.38 (q, 2H); 2.67 (m, 1H); 1.48 (t, 3H); 1.01 (m, 3H); 0.68 (m, 1H).
[0536] Ex. no. 2-304: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.93 (br s, 1H); 8.00 (s, 2H); 5.00 (br s, 2H); 4.37 (q, 2H); 2.95 (m, 1H); 1.49 (t, 3H); 1.11 (m, 2H); 1.05 (m, 2H).
[0537] Ex. no. 2-305: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.87 (br s, 1H); 7.90 (d, 1H); 7.85 (d, 1H); 4.38 (q, 2H); 4.11 (s, 2H); 3.57 (t, 2H); 3.28 (s, 3H); 2.88 (t, 2H); 1.48 (t, 3H).
[0538] Ex. no. 2-306: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.92 (br s, 1H); 7.97 (d, 1H); 7.93 (d, 1H); 4.55 (d, 1H); 4.47 (d, 1H); 4.38 (q, 2H); 3.82 (m, 1H); 3.73 (m, 1H); 3.34 (m, 1H); 3.31 (s, 3H); 3.18 (m, 1H); 1.48 (t, 3H).
[0539] Ex. no. 2-307: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.94 (br s, 1H); 7.99 (s, 2H); 5.00 (br s, 2H); 4.38 (q, 2H); 3.81 (t, 2H); 3.63 (t, 2H); 3.35 (s, 3H); 1.49 (t, 3H).
[0540] Ex. no. 2-308: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.86 (br s, 1H); 7.90 (d, 1H); 7.85 (d, 1H); 5.87 (m, 1H); 5.25 (d, 1H); 5.17 (d, 1H); 4.38 (q, 2H); 3.96 (s, 2H); 3.38 (d, 2H); 1.48 (t, 3H).
[0541] Ex. no. 2-311: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.89 (br s, 1H); 7.93 (m, 2H); 4.38 (q, 2H); 4.26 (s, 2H); 3.76 (q, 2H); 1.48 (t, 3H).
[0542] Ex. no. 2-314: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.87 (br s, 1H); 7.89 (d, 1H); 7.84 (d, 1H); 4.38 (q, 2H); 4.10 (s, 2H); 2.68 (d, 2H); 1.48 (t, 3H); 1.02 (m, 1H); 0.55 (m, 2H); 0.24 (m, 2H).
[0543] Ex. no. 2-315: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.92 (br s, 1H); 7.97 (d, 1H); 7.93 (d, 1H); 4.49 (d, 1H); 4.44 (d, 1H); 4.38 (q, 2H); 3.01 (d, 2H); 1.48 (t, 3H); 1.14 (m, 1H); 0.66 (m, 2H); 0.39 (m, 1H).
[0544] Ex. no. 2-316: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.95 (br s, 1H); 4.94 (br s, 2H); 4.38 (q, 2H);
[0545] 3.34 (d, 2H); 1.49 (t, 3H); 1.18 (m, 1H); 0.69 (m, 2H); 0.48 (m, 2H).
[0546] Ex. no. 2-320: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.79 (br s, 1H); 7.79 (d, 1H); 7.75 (d, 1H); 7.38 (t, 1H); 4.37 (q, 2H); 4.07 (s, 2H); 2.15 (s, 3H); 1.48 (t, 3H).
[0547] Ex. no. 2-321: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.88 (br s, 1H); 7.89 (d, 1H); 7.81 (d, 1H); 7.39 (t, 1H); 4.54 (s, 2H); 4.38 (q, 2H); 2.79 (s, 3H); 1.49 (t, 3H).
[0548] Ex. no. 2-322: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.84 (br s, 1H); 7.93 (d, 1H); 7.84 (d, 1H); 7.35 (t, 1H); 5.07 (s, 2H); 4.38 (q, 2H); 3.24 (s, 3H); 1.48 (t, 3H).
[0549] Ex. no. 2-323: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.79 (br s, 1H); 7.78 (d, 1H); 7.74 (d, 1H); 7.36 (t, 1H); 4.37 (q, 2H); 4.09 (s, 2H); 2.65 (q, 2H); 1.48 (t, 3H); 1.23 (t, 3H).
[0550] Ex. no. 2-324: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.85 (br s, 1H); 7.88 (d, 1H); 7.81 (d, 1H); 7.37 (t, 1H); 4.49 (s, 2H); 4.38 (q, 2H); 3.09 (m, 1H); 2.98 (m, 1H); 1.48 (t, 3H); 1.29 (t, 3H).
[0551] Ex. no. 2-325: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.85 (br s, 1H); 7.93 (d, 1H); 7.85 (d, 1H); 7.32 (t, 1H); 5.02 (s, 2H); 4.38 (q, 2H); 3.38 (q, 2H); 1.48 (t, 3H); 1.34 (t, 3H).
[0552] Ex. no. 2-338: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.82 (br s, 1H); 7.79 (d, 1H); 7.74 (d, 1H); 7.37 (t, 1H); 4.38 (q, 2H); 4.14 (s, 2H); 2.62 (d, 2H); 1.48 (t, 3H); 1.02 (m, 1H); 0.54 (m, 2H); 0.22 (m, 2H).
[0553] Ex. no. 2-339: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.84 (br s, 1H); 7.88 (d, 1H); 7.81 (d, 1H); 7.38 (t, 1H); 4.55 (d, 1H); 4.50 (d, 1H); 4.38 (q, 2H); 3.02 (m, 2H); 1.48 (t, 3H); 1.12 (m, 1H); 0.66 (m, 2H); 0.45 (m, 1H); 0.38 (m, 1H).
[0554] Ex. no. 2-340: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.86 (br s, 1H); 7.93 (d, 1H); 7.86 (d, 1H); 7.31 (t, 1H); 5.01 (s, 2H); 4.38 (q, 2H); 3.38 (d, 2H); 1.48 (t, 3H); 1.19 (m, 1H); 0.71 (m, 2H); 0.47 (m, 2H).
[0555] Ex. no. 2-353: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.74 (br s, 1H); 7.82 (d, 1H); 7.56 (d, 1H); 4.36 (q, 2H); 4.07 (s, 2H); 2.17 (s, 3H); 1.47 (t, 3H).
[0556] Ex. no. 2-354: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.78 (br s, 1H); 7.88 (d, 1H); 7.65 (d, 1H); 4.56 (d, 1H); 4.48 (d, 1H); 4.36 (q, 2H); 2.78 (s, 3H); 1.47 (t, 3H).
[0557] Ex. no. 2-355: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.80 (br s, 1H); 7.90 (d, 1H); 7.68 (d, 1H); 4.97 (br s, 2H); 4.36 (q, 2H); 3.19 (s, 3H); 1.47 (t, 3H).
[0558] Ex. no. 2-356: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.76 (br s, 1H); 7.81 (d, 1H); 7.56 (d, 1H); 4.36 (q, 2H); 4.09 (s, 2H); 2.66 (q, 2H); 1.47 (t, 3H); 1.25 (t, 3H).
[0559] Ex. no. 2-357: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.80 (br s, 1H); 7.88 (d, 1H); 7.65 (d, 1H); 4.52 (d, 1H); 4.43 (d, 1H); 4.36 (q, 2H); 3.02 (m, 1H); 2.92 (m, 1H); 1.47 (t, 3H); 1.30 (t, 3H).
[0560] Ex. no. 2-358: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.81 (br s, 1H); 7.90 (d, 1H); 7.68 (d, 1H); 4.92 (br s, 2H); 4.36 (q, 2H); 3.31 (q, 2H); 1.47 (t, 3H); 1.33 (t, 3H).
[0561] Ex. no. 2-362: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.71 (br s, 1H); 8.03 (d, 1H); 7.34 (d, 1H); 4.35 (q, 2H); 4.10 (s, 2H); 2.19 (s, 3H); 1.47 (t, 3H).
[0562] Ex. no. 2-363: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.76 (br s, 1H); 8.09 (d, 1H); 7.42 (d, 1H); 4.59 (d, 1H); 4.52 (d, 1H); 4.35 (q, 2H); 2.79 (s, 3H); 1.47 (t, 3H).
[0563] Ex. no. 2-364: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.78 (br s, 1H); 8.11 (d, 1H); 7.45 (d, 1H); 4.99 (br s, 2H); 4.35 (q, 2H); 3.19 (s, 3H); 1.47 (t, 3H).
[0564] Ex. no. 2-380: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.85 (br s, 1H); 7.93 (d, 1H); 7.79 (d, 1H); 4.40 (q, 2H); 4.04 (s, 2H); 2.23 (s, 3H); 1.49 (t, 3H).
[0565] Ex. no. 2-381: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.94 (br s, 1H); 8.00 (d, 1H); 7.88 (d, 1H); 4.49 (d, 1H); 4.46 (d, 1H); 4.40 (q, 2H); 2.82 (s, 3H); 1.49 (t, 3H).
[0566] Ex. no. 2-382: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.94 (br s, 1H); 7.98 (d, 1H); 7.85 (d, 1H); 5.00 (br s, 2H); 4.35 (q, 2H); 3.25 (s, 3H); 1.46 (t, 3H).
[0567] Ex. no. 2-383: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.86 (br s, 1H); 7.93 (d, 1H); 7.79 (d, 1H); 4.40 (q, 2H); 4.07 (s, 2H); 2.73 (q, 2H); 1.49 (t, 3H); 1.26 (t, 3H).
[0568] Ex. no. 2-384: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.91 (br s, 1H); 8.00 (d, 1H); 7.87 (d, 1H); 4.42 (m, 4H); 3.08 (m, 1H); 2.96 (m, 1H); 1.49 (t, 3H); 1.30 (t, 3H).
[0569] Ex. no. 2-385: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.94 (br s, 1H); 8.01 (d, 1H); 7.93 (d, 1H); 4.96 (br s, 2H); 4.40 (q, 2H); 3.37 (q, 2H); 1.49 (t, 3H); 1.34 (t, 3H).
[0570] Ex. no. 2-404: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.78 (br s, 1H); 7.78 (d, 1H); 7.73 (d, 1H); 7.38 (t, 1H); 4.39 (q, 2H); 4.09 (br s, 2H); 2.16 (s, 3H); 1.48 (t, 3H).
[0571] Ex. no. 2-405: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.82 (br s, 1H); 7.85 (d, 1H); 7.83 (d, 1H); 7.40 (t, 1H); 4.59 (d, 1H); 4.52 (d, 1H); 4.40 (q, 2H); 2.81 (s, 3H); 1.49 (t, 3H).
[0572] Ex. no. 2-406: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.82 (br s, 1H); 7.88 (br s, 1H); 7.36 (t, 1H); 5.10 (s, 2H); 4.40 (q, 2); 3.24 (s, 3H); 1.49 (t, 3H).
[0573] Ex. no. 2-407: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.77 (br s, 1H); 7.78 (d, 1H); 7.72 (d, 1H); 7.36 (t, 1H); 4.39 (q, 2H); 4.12 (br s, 2H); 2.67 (q, 2H); 1.48 (t, 3H); 1.24 (t, 3H).
[0574] Ex. no. 2-408: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.83 (br s, 1H); 7.85 (d, 1H); 7.82 (d, 1H), 7.37 (t, 1H); 4.55 (d, 1H); 4.48 (d, 1H); 4.40 (q, 2H); 3.10 (m, 1H); 2.99 (m, 1H); 1.48 (t, 3H); 1.30 (t, 3H).
[0575] Ex. no. 2-409: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.89 (br s, 1H); 7.87 (d, 1H); 7.84 (d, 1H); 7.33 (t, 1H); 5.04 (br s, 2H); 4.38 (q, 2H); 3.40 (q, 2H); 3.32 (s, 3H); 1.48 (t, 3H); 1.35 (t, 3H).
[0576] Ex. no. 2-493: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.68 (br s, 1H); 7.74 (d, 1H); 7.71 (d, 1H); 4.36 (q, 2H); 4.04 (s, 2H); 2.96 (q, 2H); 2.11 (m, 1H); 1.48 (t, 3H); 1.24 (t, 3H); 0.91 (m, 2H); 0.51 (m, 2H).
[0577] Ex. no. 2-559: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ=10.34 (br s, 1H); 7.58 (d, 1H); 7.49 (d, 1H); 4.49 (q, 2H); 4.10 (s, 3H); 2.19 (s, 3H); 1.63 (t, 3H).
[0578] Ex. no. 2-561: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ=10.4 (br s, 1H); 7.68 (d, 1H); 7.58 (d, 1H); 4.88 (s, 2H); 4.48 (q, 2H); 3.05 (s, 3H); 1.61 (t, 3H).
[0579] Ex. no. 3-37: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.65 (br s, 1H); 7.98 (d, 1H); 7.73 (d, 1H); 4.36 (s, 2H); 4.31 (t, 2H); 3.40 (s, 3H); 2.56 (s, 3H); 2.21 (s, 3H); 1.89 (m, 2H); 0.89 (t, 3H).
[0580] Ex. no. 3-38: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.71 (br s, 1H); 8.05 (d, 1H); 7.80 (d, 1H); 4.99 (d, 1H); 4.64 (d, 1H); 3.41 (s, 3H); 2.81 (s, 3H); 2.53 (s, 3H); 1.89 (m, 2H); 0.89 (t, 3H).
[0581] Ex. no. 3-39: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.72 (br s, 1H); 8.11 (d, 2H); 7.85 (d, 1H); 5.41 (br s, 2H); 4.31 (t, 2H); 3.40 (s, 3H); 3.19 (s, 3H); 2.58 (s, 3H); 1.90 (m, 2H); 0.89 (t, 3H).
[0582] Ex. no. 3-86: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ=10.59 (br s, 1H); 7.67 (m, 2H); 4.42 (t, 2H); 3.94 (s, 2H); 2.67 (s, 3H); 2.66 (m, 2H); 2.03 (m, 2H); 1.31 (t, 3H); 0.99 (t, 3H).
[0583] Ex. no. 3-88: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.70 (br s, 1H); 7.83 (d, 1H); 7.79 (d, 1H); 4.84 (br s, 2H); 4.31 (t, 2H); 3.33 (m, 3H); 2.58 (s, 3H); 1.90 (m, 2H); 1.33 (t, 3H); 0.89 (t, 3H).
[0584] Ex. no. 3-107: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.53 (br s, 1H); 7.64 (d, 1H); 7.61 (d, 1H); 7.36 (t, 1H); 4.32 (t, 2H); 3.98 (s, 2H); 2.50 (s, 3H); 2.16 (s, 3H); 1.91 (m, 2H); 0.90 (t, 3H).
[0585] Ex. no. 3-108: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.57 (br s, 1H); 7.69 (d, 1H); 7.65 (d, 1H); 7.38 (t, 1H); 4.45 (d, 1H); 4.36 (d, 1H); 4.31 (t, 2H); 2.81 (s, 3H); 2.46 (s, 3H); 1.89 (m, 2H); 0.89 (t, 3H).
[0586] Ex. no. 3-109: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.59 (br s, 1H); 7.75 (d, 1H); 7.69 (d, 1H); 7.33 (t, 1H); 4.94 (s, 2H); 4.30 (t, 3H); 3.25 (s, 3H); 2.52 (s, 3H); 1.89 (m, 2H); 0.89 (t, 3H).
[0587] Ex. no. 3-134: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ=9.94 (br s, 1H); 8.07 (d, 1H); 7.64 (d, 1H); 4.37 (t, 2H); 4.12 (s, 3H); 3.96 (s, 2H); 2.25 (s, 3H); 2.02 (m, 2H); 0.98 (t, 3H).
[0588] Ex. no. 3-135: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ=10.01 (br s, 1H); 8.10 (d, 1H); 7.70 (d, 1H); 4.44 (d, 1H); 4.36 (t, 2H); 4.18 (d, 1H); 4.07 (s, 3H); 2.76 (s, 3H); 2.02 (m, 2H); 0.98 (t, 3H).
[0589] Ex. no. 3-136: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ=9.82 (br s, 1H); 8.14 (d, 1H); 7.71 (d, 1H); 4.72 (s, 2H); 4.35 (t, 2H); 4.08 (s, 3H); 3.07 (s, 3H); 2.02 (m, 2H); 0.98 (t, 3H).
[0590] Ex. no. 3-161: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.67 (br s, 1H); 7.91 (d, 1H); 7.72 (d, 1H); 4.38 (t, 2H); 4.19 (s, 2H); 2.46 (s, 3H); 2.22 (s, 3H); 1.92 (m, 2H); 0.91 (t, 3H).
[0591] Ex. no. 3-162: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.72 (br s,1H); 8.00 (d, 1H); 7.82 (d, 1H); 4.64 (d, 1H); 4.59 (d, 1H); 4.38 (t, 2H); 2.80 (s, 3H); 2.40 (s, 3H); 1.92 (m, 2H); 0.91 (t, 3H).
[0592] Ex. no. 3-163: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.75 (br s, 1H); 8.02 (d, 1H); 7.87 (d, 1H); 5.15 (br s, 2H); 4.38 (t, 2H); 3.23 (t, 3H); 2.39 (s, 3H); 1.92 (m, 2H); 0.91 (t, 3H).
[0593] Ex. no. 3-170: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.59 (br s, 1H); 7.79 (d, 1H); 7.67 (d, 1H); 7.39 (t, 1H); 4.38 (t, 2H); 2.43 (s, 3H); 2.17 (s, 3H); 1.91 (m, 2H); 0.90 (t, 3H).
[0594] Ex. no. 3-171: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.64 (br s, 1H); 7.86 (d, 1H); 7.76 (d, 1H); 7.41 (t, 1H); 4.72 (d, 1H); 4.66 (d, 1H); 2.80 (s, 3H); 2.38 (s, 3H); 1.92 (m, 2H); 0.90 (t, 3H).
[0595] Ex. no. 3-172: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.66 (br s, 1H); 7.90 (d, 1H); 7.82 (d, 1H); 7.38 (t, 1H); 5.25 (br s, 2H); 4.38 (t, 2H); 3.22 (s, 3H); 2.38 (s, 3H); 1.92 (m, 2H); 0.91 (t, 3H).
[0596] Ex. no. 3-199: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.94 (br s, 1H); 8.38 (d, 1H); 8.11 (d, 1H); 6.19 (d, 1H); 4.88 (d, 1H); 4.36 (t, 2H); 3.65 (s, 3H); 3.27 (s, 3H); 1.90 (m, 2H); 0.91 (t, 3H).
[0597] Ex. no. 3-287: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.57 (br s, 1H); 7.48 (d, 1H); 7.34 (d, 1H); 4.30 (t, 2H); 3.96 (s, 2H); 2.48 (s, 3H); 2.13 (s, 3H); 1.88 (m, 2H); 0.88 (t, 3H).
[0598] Ex. no. 3-289: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.64 (br s, 1H); 7.59 (d, 1H); 7.41 (d, 1H); 4.86 (s, 2H); 4.31 (t, 2H); 3.15 (s, 3H); 2.54 (s, 3H); 1.89 (m, 2H); 0.88 (t, 3H).
[0599] Ex. no. 3-296: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ=10.00 (br s, 1H); 7.74 (d, 1H); 7.67 (d, 1H); 4.43 (t, 2H); 4.05 (s, 3H); 2.23 (s, 3H); 2.04 (m, 2H); 1.00 (t, 3H).
[0600] Ex. no. 3-297: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.90 (br s, 1H); 7.97 (d, 1H); 7.92 (d, 1H); 4.48 (d, 1H); 4.43 (d, 1H); 4.33 (t, 2H); 2.82 (s, 3H); 1.90 (m, 2H); 0.89 (t, 3H).
[0601] Ex. no. 3-298: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.92 (br s, 1H); 8.00 (m, 2H); 4.98 (br s, 2H); 4.33 (t, 2H); 3.25 (s, 3H); 1.90 (m, 2H); 0.89 (t, 3H).
[0602] Ex. no. 3-299: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.86 (br s, 1H); 7.90 (d, 1H); 7.84 (d, 1H); 4.33 (t, 2H); 4.05 (s, 3H); 2.72 (q, 2H); 1.90 (m, 2H); 1.25 (t, 3H); 0.89 (t, 3H).
[0603] Ex. no. 3-301: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ=10.60 (br s, 1H); 7.80 (d, 1H); 7.77 (d, 1H); 4.83 (s, 2H); 4.38 (t, 2H); 3.19 (q, 2H); 2.02 (m, 2H); 1.47 (t, 3H); 0.98 (t, 3H).
[0604] Ex. no. 3-308: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.85 (br s, 1H); 87.90 (d, 1H); 7.84 (d, 1H); 5.88 (m, 1H); 5.26 (d, 1H); 5.17 (d, 1H); 4.33 (t, 2H); 3.96 (s, 2H); 3.38 (d, 2H); 1.90 (m, 2H); 0.89 (t, 3H).
[0605] Ex. no. 3-311: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.87 (br s, 1H); 7.93 (d, 1H); 7.89 (d, 1H); 4.33 (t, 2H); 4.26 (s, 2H); 3.76 (q, 2H); 1.90 (m, 2H); 0.89 (t, 3H).
[0606] Ex. no. 3-314: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.85 (br s, 1H); 7.90 (d, 1H); 7.83 (d, 1H); 4.33 (t, 2H); 4.10 (s, 2H); 2.68 (d, 2H); 1.90 (m, 2H); 1.02 (m, 1H); 0.89 (t, 3H); 0.55 (m, 2H); 0.25 (m, 2H).
[0607] Ex. no. 3-320: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.78 (br s, 1H); 7.76 (m, 2H); 7.38 (t, 1H); 4.32 (t, 2H); 4.07 (s, 2H); 2.15 (s, 3H); 1.89 (m, 2H); 0.89 (t, 3H).
[0608] Ex. no. 3-322: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.83 (br s, 1H); 7.92 (d, 1H); 7.86 (d, 1H); 7.35 (t, 1H); 5.07 (s, 2H); 4.33 (t, 2H); 3.24 (s, 3H); 1.89 (m, 2H); 0.89 (t, 3H).
[0609] Ex. no. 3-323: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.77 (br s, 1H); 7.75 (m, 2H); 7.36 (t, 1H); 4.32 (t, 2H); 4.09 (s, 2H); 2.65 (q, 2H); 1.89 (m, 2H); 1.23 (t, 3H); 0.89 (t, 3H).
[0610] Ex. no. 3-324: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=10.88 (br s, 1H); 7.64 (s, 2H); 7.16 (t, 1H); 4.39 (t, 2H); 4.32 (s, 3H); 2.95 (m, 2H); 2.00 (m, 2H); 1.39 (t, 3H); 0.98 (t, 3H).
[0611] Ex. no. 3-325: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.95 (br s, 1H); 7.86 (d, 1H); 7.82 (d, 1H); 7.37 (t, 1H); 4.49 (s, 2H); 4.33 (t, 2H); 3.09 (m, 1H); 2.98 (m, 1H); 1.88 (m, 2H); 1.29 (t, 3H); 0.89 (t, 3H).
[0612] Ex. no. 3-362: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.70 (br s, 1H); 8.03 (d, 1H); 7.33 (d, 1H); 4.30 (t, 2H); 4.10 (s, 2H); 2.19 (s, 3H); 1.88 (m, 2H); 0.88 (t, 3H).
[0613] Ex. no. 3-363: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): 11.74 (br s, 1H); 8.09 (d, 1H); 7.41 (d, 1H); 4.59 (d, 1H); 4.52 (d, 1H); 4.30 (t, 2H); 2.79 (s, 3H); 1.88 (m, 2H); 0.88 (t, 3H).
[0614] Ex. no. 3-380: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.83 (br s, 1H); 7.93 (d, 1H); 7.78 (d, 1H); 4.35 (t, 2H); 4.04 (s, 2H); 2.23 (s, 3H); 1.91 (m, 2H); 0.90 (t, 3H).
[0615] Ex. no. 3-381: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.94 (br s, 1H); 8.00 (d, 1H); 7.86 (d, 1H); 4.50 (d, 1H); 4.45 (d, 1H); 4.35 (t, 2H); 2.82 (s, 3H); 1.89 (m, 2H); 0.89 (t, 3H).
[0616] Ex. no. 3-382: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.91 (br s, 1H); 8.01 (d, 1H); 7.88 (d, 1H); 5.00 (br s, 2H); 4.33 (t, 3H); 3.26 (s, 3H); 1.90 (m, 2H); 0.89 (t, 3H).
[0617] Ex. no. 3-383: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.84 (br s, 1H); 7.93 (d, 1H); 7.77 (d, 1H); 4.35 (t, 2H); 4.07 (s, 2H); 2.73 (q, 2H); 1.91 (m, 2H); 1.26 (t, 3H); 0.89 (t, 3H).
[0618] Ex. no. 3-384: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.89 (br s, 1H); 8.00 (d, 1H); 7.86 (d, 1H); 4.47 (d, 1H); 4.40 (d, 1H); 4.35 (t, 2H); 3.09 (m, 1H); 2.98 (m, 1H); 1.91 (m, 2H; 1.30 (t, 3H); 0.89 (t, 3H).
[0619] Ex. no. 3-385: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ=11.98 (br s, 1H); 7.97 (d,1H); 7.83 (d, 1H); 4.94 (br s, 2H); 4.29 (t, 2H); 3.37 (q, 2H); 1.91 (s, 3H); 1.87 (q, 2H); 1.34 (t, 3H); 0.89 (t, 3H).
[0620] B. Formulation Examples [0621] a) A dusting product 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 the mixture in a hammer mill. [0622] b) A readily water-dispersible, wettable powder is obtained by mixing 25 parts by weight of a compound of the formula (I) and/or salts thereof, 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurate as a wetting agent and dispersant, and grinding the mixture in a pinned-disk mill. [0623] c) A readily water-dispersible dispersion concentrate is obtained by mixing 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 above 277 C), and grinding the mixture in a friction ball mill to a fineness of below 5 microns. [0624] d) An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula
[0625] (I) and/or salts thereof, 75 parts by weight of cyclohexanone as a solvent and 10 parts by weight of ethoxylated nonylphenol as an emulsifier. [0626] e) Water-dispersible granules are obtained by mixing [0627] 75 parts by weight of a compound of the formula (I) and/or salts thereof, [0628] 10 parts by weight of calcium lignosulfonate, [0629] 5 parts by weight of sodium lauryl sulfate, [0630] 3 parts by weight of polyvinyl alcohol and [0631] 7 parts by weight of kaolin, [0632] grinding the mixture in a pinned-disk mill, and granulating the powder in a fluidized bed by spray application of water as a granulating liquid. [0633] f) Water-dispersible granules are also obtained by homogenizing and precomminuting, in a colloid mill, [0634] 25 parts by weight of a compound of the formula (I) and/or salts thereof, [0635] 5 parts by weight of sodium 2,2′-dinaphthylmethane-6,6′-disulfonate [0636] 2 parts by weight of sodium oleoylmethyltaurate, [0637] 1 part by weight of polyvinyl alcohol, [0638] 17 parts by weight of calcium carbonate and [0639] 50 parts by weight of water, [0640] then grinding the mixture in a bead mill and atomizing and drying the resulting suspension in a spray tower by means of a one-phase nozzle.
[0641] C. Biological Examples
[0642] 1. Pre-Emergence Herbicidal Action Against Harmful Plants
[0643] Seeds of monocotyledonous and dicotyledonous weed plants and crop plants are laid out in sandy loam soil in wood-fiber pots and covered with soil. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), are then applied to the surface of the covering soil in the form of an aqueous suspension or emulsion at a water application rate equating to 600 to 800 l/ha, with addition of 0.2% wetting agent. After the treatment, the pots are placed in a greenhouse and kept under good growth conditions for the trial plants. The damage to the test plants is scored visually after a test period of 3 weeks by comparison with untreated controls (herbicidal activity in percent (%): 100% activity=the plants have died, 0% activity=like control plants). Numerous compounds of the invention showed very good action against a multitude of important harmful plants. The tables below illustrate, in an exemplary manner, the post-emergence herbicidal action of the compounds according to the invention, the herbicidal activity being stated in percent.
[0644] The Abbreviations Used for the Harmful Plants Mean:
TABLE-US-00005 ABUTH Abutilon theophrasti ALOMY Alopecurus myosuroides AVEFA Avena fatua AMARE Amaranthus retroflexus CYPES Cyperus esculentus DIGSA Digitaria sanguinalis ECHCG Echinochloa crus-galli HORMU Hordeum murinum LOLMU Lolium multiflorum LOLRI Lolium rigidum MATIN Matricaria inodora PHBPU Pharbitis purpurea POLCO Polygonum convolvulus SETVI Setaria viridis STEME Stellaria media VERPE Veronica persica VIOTR Viola tricolor
TABLE-US-00006 Example Dosage No. [g/ha] DIGSA ECHCG LOLRI SETVI ABUTH AMARE MATIN PHBPU POLCO STEME VIOTR VERPE HORMU 2-300 320 100 100 100 100 100 100 100 100 100 100 100 100 100 2-315 320 100 100 90 100 100 100 100 90 90 100 100 100 100 2-324 320 100 100 90 100 100 100 100 100 100 100 100 100 100 1-316 320 100 100 90 100 100 100 100 90 100 100 100 100 90 1-312 320 100 100 90 100 100 100 100 90 90 100 100 100 100 1-300 320 100 100 100 100 100 100 100 100 100 100 100 100 100 1-363 320 100 100 100 100 100 100 100 100 90 100 100 100 100 1-364 320 100 100 80 100 100 100 100 90 100 100 100 100 90 1-306 320 100 100 90 90 100 100 100 90 80 100 100 90 90
TABLE-US-00007 Example Dosage No. [g/ha] ECHCG LOLRI SETVI ABUTH AMARE MATIN PHBPU POLCO STEME VIOTR VERPE HORMU 3-162 320 100 90 100 100 100 100 90 100 100 100 100 100 1-302 320 100 100 100 100 100 100 100 100 100 100 100 100 1-303 320 100 100 100 100 100 100 100 100 100 100 100 100 1-314 320 100 100 100 100 100 100 90 100 90 100 100 100 1-304 320 100 100 100 100 100 100 100 100 100 100 100 100 1-162 320 100 90 100 100 100 100 90 100 100 100 90 80 2-305 320 100 100 100 100 100 100 100 100 100 100 100 100
TABLE-US-00008 Example Dosage No. [g/ha] DIGSA ECHCG SETVI ABUTH AMARE MATIN PHBPU POLCO STEME VIOTR VERPE HORMU 1-171 320 100 100 100 100 100 100 90 100 100 100 100 80 1-552 320 100 100 100 100 100 100 90 90 100 100 100 80 3-171 320 100 100 100 100 100 100 90 90 100 100 100 90 3-172 320 100 100 100 100 100 100 80 100 100 100 100 80
TABLE-US-00009 Example Dosage No. [g/ha] ECHCG LOLMU SETVI ABUTH AMARE MATIN PHBPU POLCO STEME VIOTR VERPE 3-384 320 100 90 100 100 100 100 90 80 90 100 100 2-384 320 100 100 100 100 100 100 90 90 100 100 100 2-385 320 100 100 100 100 100 100 80 100 100 100 100 1-83 320 100 100 100 100 100 100 80 100 100 100 100 2-296 320 100 100 100 100 100 100 90 100 100 100 100 2-320 320 100 90 100 100 100 100 80 90 100 100 100 1-323 320 100 100 100 100 100 90 100 100 100 100 100 2-323 320 100 100 100 100 100 100 90 100 100 100 100 3-323 320 100 100 100 100 100 100 100 100 100 100 100 1-322 320 100 100 100 100 100 100 100 100 100 100 100 2-322 320 100 100 100 100 100 90 100 100 100 100 100 3-322 320 100 80 100 100 100 100 90 100 100 100 100 2-325 320 100 100 100 100 100 100 100 100 100 100 100 1-325 320 100 100 100 100 100 100 100 100 100 100 100 1-383 320 100 100 100 100 100 100 80 100 100 100 100 1-182 320 100 90 100 100 100 100 80 100 90 100 100 1-299 320 100 100 100 100 100 100 90 90 100 100 100 2-299 320 100 100 100 100 100 100 90 90 100 100 100 2-297 320 100 90 100 100 100 100 90 80 100 100 100 1-384 320 100 100 100 100 100 100 90 90 100 100 100 2-298 320 100 90 100 100 100 100 80 90 90 100 100 3-298 320 100 90 100 100 100 100 90 80 90 100 100
TABLE-US-00010 Example Dosage No. [g/ha] ECHCG LOLRI SETVI ABUTH AMARE MATIN POLCO STEME VIOTR VERPE HORMU 2-311 320 100 90 100 100 100 100 80 100 100 90 80
TABLE-US-00011 Example Dosage No. [g/ha] ECHCG LOLRI SETVI ABUTH AMARE MATIN PHBPU STEME VIOTR VERPE HORMU 1-311 320 100 100 100 100 100 100 100 100 100 100 100 3-314 320 90 90 100 100 100 100 80 100 100 100 90 1-362 320 100 80 100 100 100 100 80 100 100 100 80 1-305 320 100 90 100 100 100 100 90 100 100 100 100 2-363 320 100 100 100 100 100 100 80 100 100 100 100 3-308 320 100 80 100 100 100 100 100 100 100 100 80
TABLE-US-00012 Example Dosage No. [g/ha] ECHCG SETVI ABUTH AMARE MATIN PHBPU POLCO STEME VIOTR VERPE HORMU 2-162 320 100 100 100 100 100 90 100 100 100 90 90 1-163 320 100 100 100 100 100 80 100 100 100 100 90 3-163 320 100 100 100 100 100 80 80 100 100 100 90
TABLE-US-00013 Example Dosage No. [g/ha] DIGSA ECHCG SETVI ABUTH AMARE MATIN PHBPU POLCO STEME VIOTR VERPE 2-171 320 100 100 100 100 100 100 90 90 100 100 100 3-170 320 100 100 100 100 100 100 80 90 100 100 100
TABLE-US-00014 Example Dosage No. [g/ha] DIGSA ECHCG SETVI ABUTH AMARE MATIN POLCO STEME VIOTR VERPE HORMU 2-170 320 100 100 100 100 100 100 100 100 100 100 80
TABLE-US-00015 Example Dosage No. [g/ha] ECHCG LOLRI SETVI ABUTH AMARE MATIN PHBPU POLCO STEME VIOTR HORMU 3-325 320 100 100 100 100 100 100 100 100 100 100 100 3-324 320 100 100 100 100 100 100 90 100 100 100 100
TABLE-US-00016 Example Dosage No. [g/ha] ECHCG LOLRI SETVI ABUTH AMARE MATIN PHBPU POLCO STEME VIOTR VERPE 1-308 320 100 90 100 100 100 100 100 100 100 100 100
TABLE-US-00017 Example Dosage No. [g/ha] ECHCG LOLMU SETVI ABUTH AMARE MATIN POLCO STEME VIOTR VERPE 1-385 320 100 100 100 100 100 100 90 90 100 100 2-161 320 100 80 100 100 100 100 90 100 100 100 1-561 320 100 80 100 100 100 90 100 90 100 90 3-385 320 100 90 100 100 100 100 80 90 100 100 1-191 320 100 80 100 100 100 100 100 100 100 100 3-296 320 100 80 100 100 100 100 90 100 100 100 2-382 320 100 80 100 100 100 100 90 90 100 100 2-383 320 100 100 100 100 100 100 90 100 100 100 3-383 320 100 80 100 100 100 100 90 100 100 100 3-299 320 100 90 100 100 100 100 90 90 100 100
TABLE-US-00018 Example Dosage No. [g/ha] ECHCG SETVI ABUTH AMARE MATIN PHBPU POLCO STEME VIOTR VERPE 2-380 320 100 100 100 100 100 80 90 80 100 100 1-280 320 100 80 90 100 90 80 80 90 90 100 1-381 320 100 100 100 100 100 80 90 90 100 100 1-320 320 100 100 100 90 100 80 90 90 100 100 2-163 320 100 100 100 100 100 90 100 90 100 100 1-107 320 100 100 100 100 100 90 80 90 90 100 1-301 320 100 100 100 100 100 100 100 90 100 100
TABLE-US-00019 Example Dosage No. [g/ha] ECHCG LOLMU SETVI ABUTH AMARE MATIN PHBPU STEME VIOTR VERPE 2-381 320 100 80 100 100 100 100 80 90 100 100 1-297 320 100 100 100 100 100 100 90 90 100 100 1-298 320 100 90 100 100 100 100 90 100 100 100
TABLE-US-00020 Example Dosage No. [g/ha] ECHCG SETVI ABUTH AMARE MATIN POLCO STEME VIOTR VERPE 2-107 320 100 100 100 100 100 80 90 100 100 3-107 320 100 100 100 100 100 90 100 100 100 2-136 320 100 80 100 100 100 100 100 100 100 1-242 320 100 100 100 100 100 80 90 100 100 3-136 320 100 100 100 100 100 80 100 100 100 3-320 320 100 100 100 100 100 90 100 100 100 1-289 320 90 90 90 100 100 80 90 90 100 1-382 320 100 100 100 100 100 90 90 100 100 3-381 320 100 90 100 100 100 80 90 100 100 1-85 320 100 100 100 100 100 90 100 100 100 1-134 320 100 100 100 100 100 80 100 100 100 2-135 320 100 100 100 100 100 90 90 100 100 3-134 320 100 100 100 100 100 80 100 100 100
TABLE-US-00021 Example Dosage No. [g/ha] ECHCG SETVI ABUTH AMARE MATIN PHBPU POLCO VIOTR VERPE 1-109 320 90 100 100 100 90 80 90 100 80 1-86 320 100 100 100 100 100 80 100 100 100 3-380 320 100 100 100 100 100 90 80 100 90
TABLE-US-00022 Example Dosage No. [g/ha] ECHCG LOLMU SETVI ABUTH AMARE MATIN STEME VIOTR VERPE 1-296 320 100 90 100 100 100 100 100 100 100 1-161 320 100 90 100 100 100 100 100 100 100
TABLE-US-00023 Example Dosage No. [g/ha] ECHCG SETVI ABUTH AMARE MATIN PHBPU STEME VIOTR VERPE 1-243 320 100 100 100 100 100 80 90 100 100 1-244 320 100 100 100 100 100 90 90 100 100 3-88 320 100 100 100 100 100 90 80 100 100 1-134 320 100 100 100 100 100 80 90 100 100 1-380 320 100 100 100 100 100 80 90 100 100 3-297 320 100 100 100 100 100 80 100 100 100
TABLE-US-00024 Example Dosage No. [g/ha] ECHCG SETVI ABUTH AMARE MATIN POLCO STEME VIOTR HORMU 2-362 320 100 100 100 100 100 100 100 100 90
TABLE-US-00025 Example Dosage No. [g/ha] ECHCG SETVI ABUTH MATIN PHBPU POLCO STEME VIOTR VERPE 1-84 320 100 100 100 100 80 90 100 100 100
TABLE-US-00026 Example Dosage No. [g/ha] ECHCG SETVI ABUTH AMARE MATIN STEME VIOTR VERPE HORMU 3-363 320 100 100 100 100 100 100 100 90 100
TABLE-US-00027 Example Dosage No. [g/ha] ECHCG ABUTH AMARE MATIN POLCO STEME VIOTR VERPE 1-570 320 90 90 100 100 80 80 80 80 1-288 320 90 90 100 100 80 90 90 90
TABLE-US-00028 Example Dosage No. [g/ha] ECHCG SETVI ABUTH AMARE MATIN POLCO STEME VIOTR 3-135 320 100 100 100 100 100 90 100 100
TABLE-US-00029 Example Dosage No. [g/ha] ECHCG SETVI ABUTH AMARE MATIN STEME VIOTR VERPE 2-559 320 100 90 100 100 90 90 100 100 1-559 320 100 80 100 100 90 90 100 90 2-280 320 100 90 100 100 90 80 90 100 1-287 320 80 90 100 90 90 90 90 100 3-311 320 80 100 100 100 100 90 100 100 3-161 320 100 90 100 100 100 100 100 100 2-301 320 100 100 100 100 100 80 100 100 3-301 320 100 100 100 100 100 90 100 100
TABLE-US-00030 Example Dosage No. [g/ha] ECHCG SETVI ABUTH AMARE MATIN PHBPU VIOTR VERPE 1-88 320 100 100 100 100 100 90 100 100
TABLE-US-00031 Example Dosage No. [g/ha] ECHCG SETVI ABUTH AMARE MATIN POLCO VIOTR VERPE 2-86 320 100 100 100 100 100 80 100 100 3-86 320 100 90 100 100 100 90 100 100 1-108 320 100 100 100 100 90 90 100 90
TABLE-US-00032 Example Dosage No. [g/ha] ECHCG SETVI ABUTH AMARE MATIN VIOTR VERPE 2-88 320 100 100 100 100 100 100 100 3-39 320 90 80 100 100 100 100 100 3-108 320 90 90 100 100 100 100 90 2-108 320 90 100 100 100 100 100 100
TABLE-US-00033 Example Dosage No. [g/ha] ECHCG ABUTH AMARE MATIN STEME VIOTR VERPE 3-382 320 90 100 100 100 100 90 100 1-136 320 100 100 100 90 80 80 100 1-135 320 100 100 100 90 80 90 100
TABLE-US-00034 Example Dosage No. [g/ha] ECHCG SETVI AMARE MATIN STEME VIOTR VERPE 2-287 320 100 90 100 100 80 90 100
TABLE-US-00035 Example Dosage No. [g/ha] ECHCG AMARE MATIN POLCO STEME VIOTR VERPE 1-229 320 100 100 90 100 100 100 100
TABLE-US-00036 Example Dosage No. [g/ha] ECHCG SETVI AMARE MATIN POLCO STEME VERPE 2-289 320 100 100 100 100 80 90 90
TABLE-US-00037 Example Dosage No. [g/ha] ABUTH AMARE MATIN PHBPU STEME VIOTR VERPE 3-199 320 100 90 100 80 80 100 100
TABLE-US-00038 Example Dosage No. [g/ha] ECHCG ABUTH AMARE MATIN VIOTR VERPE 3-109 320 100 100 100 100 100 90
TABLE-US-00039 Example Dosage No. [g/ha] ABUTH AMARE MATIN STEME VIOTR VERPE 3-37 320 80 100 90 90 100 100
TABLE-US-00040 Example Dosage No. [g/ha] ECHCG AMARE MATIN STEME VIOTR VERPE 3-287 320 100 100 100 90 80 90 2-39 320 90 100 100 100 100 100
TABLE-US-00041 Example Dosage No. [g/ha] ECHCG ABUTH AMARE MATIN POLCO VERPE 3-289 320 100 80 100 100 80 90
TABLE-US-00042 Example Dosage No. [g/ha] AMARE MATIN POLCO STEME VIOTR VERPE 3-38 320 90 100 80 90 100 100
TABLE-US-00043 Ex- ample Dosage No. [g/ha] ECHCG ABUTH AMARE STEME VERPE 1-278 320 90 90 100 80 90
TABLE-US-00044 Ex- ample Dosage No. [g/ha] ABUTH AMARE MATIN VIOTR VERPE 1-37 320 80 100 80 100 90
TABLE-US-00045 Ex- ample Dosage No. [g/ha] ECHCG AMARE MATIN STEME VERPE 2-288 320 100 100 90 90 100
TABLE-US-00046 Example Dosage No. [g/ha] ABUTH AMARE MATIN VERPE 2-278 320 100 90 90 100
TABLE-US-00047 Example Dosage No. [g/ha] ECHCG AMARE STEME VERPE 2-37 320 90 100 90 100
TABLE-US-00048 Example Dosage No. [g/ha] AMARE MATIN STEME VERPE 1-38 320 80 90 90 100
TABLE-US-00049 Example Dosage No. [g/ha] ECHCG ABUTH AMARE VERPE 1-572 320 80 80 100 80
TABLE-US-00050 Example Dosage No. [g/ha] ECHCG AMARE MATIN VERPE 1-199 320 90 90 90 100
TABLE-US-00051 Example Dosage No. [g/ha] AMARE MATIN VERPE 1-39 320 100 100 90
TABLE-US-00052 Example Dosage No. [g/ha] ABUTH AMARE STEME 1-313 320 100 100 90
TABLE-US-00053 Example Dosage No. [g/ha] ABUTH AMARE VERPE 1-571 320 100 90 80
TABLE-US-00054 Example Dosage No. [g/ha] VIOTR 3-362 320 80
[0645] 2. Post-Emergence Herbicidal Action Against Harmful Plants
[0646] Seeds of monocotyledonous and dicotyledonous weed and crop plants are laid out in sandy loam soil in wood-fiber pots, covered with soil and cultivated in a greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants are treated at the one-leaf stage. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), are then sprayed onto the green parts of the plants in the form of an aqueous suspension or emulsion at a water application rate equating to 600 to 800 l/ha, with addition of 0.2% wetting agent. After the test plants have been left to stand in the greenhouse under optimal growth conditions for about 3 weeks, the action of the preparations is assessed visually in comparison to untreated controls (herbicidal action in percent (%): 100% activity=the plants have died, 0% activity=like control plants). Numerous compounds of the invention showed very good action against a multitude of important harmful plants. The tables below illustrate, in an exemplary manner, the post-emergence herbicidal action of the compounds according to the invention, the herbicidal activity being stated in percent.
TABLE-US-00055 Example Dosage number [g/ha] ALOMY AVEFA CYPES ECHCG LOLRI SETVI ABUTH AMARE 2-305 80 100 80 100 100 80 100 100 100 1-162 80 100 100 80 100 80 100 100 100 1-302 80 100 100 80 100 90 100 100 100 1-303 80 100 100 80 100 90 100 100 100 1-304 80 100 100 90 100 80 90 100 100 1-314 80 100 100 80 100 90 100 100 100 1-305 80 100 100 90 100 100 100 100 100 Example Dosage number [g/ha] MATIN PHBPU POLCO STEME VIOTR VERPE HORMU 2-305 80 100 100 100 100 100 100 100 1-162 80 100 100 90 100 100 100 90 1-302 80 90 100 100 100 100 90 90 1-303 80 100 100 100 100 100 100 100 1-304 80 90 100 100 100 100 100 80 1-314 80 100 100 100 100 100 100 100 1-305 80 100 100 100 100 100 90 90
TABLE-US-00056 Ex- ample Dosage No. [g/ha] ALOMY AVEFA DIGSA ECHCG LOLRI 1-300 80 90 100 100 100 90 2-300 80 90 100 100 100 80 Ex- ample Dosage No. [g/ha] SETVI ABUTH AMARE MATIN PHBPU 1-300 80 90 90 100 100 90 2-300 80 100 90 100 90 90 Ex- ample Dosage No. [g/ha] POLCO STEME VIOTR VERPE HORMU 1-300 80 100 100 100 100 90 2-300 80 100 100 100 100 90
TABLE-US-00057 Ex- ample Dosage No. [g/ha] ALOMY AVEFA CYPES ECHCG LOLMU SETVI ABUTH 1-323 80 90 100 80 100 90 100 100 2-323 80 80 100 80 100 80 100 100 1-83 80 80 90 90 90 80 100 90 1-299 80 90 90 80 90 90 90 100 2-299 80 90 100 90 90 90 100 100 1-384 80 90 100 90 100 90 90 100 1-381 80 80 100 90 90 80 100 100 2-296 80 100 100 80 90 90 90 100 1-385 80 90 100 80 90 80 100 100 1-297 80 100 100 80 100 100 80 80 2-86 80 90 100 80 90 90 90 80 1-298 80 100 100 90 90 80 100 80 Ex- ample Dosage No. [g/ha] AMARE MATIN PHBPU POLCO STEME VIOTR VERPE 1-323 80 90 100 100 90 100 100 100 2-323 80 80 90 90 100 100 100 100 1-83 80 100 100 100 90 100 90 100 1-299 80 100 90 90 80 100 100 100 2-299 80 90 100 90 90 100 100 100 1-384 80 90 90 90 90 90 100 100 1-381 80 100 90 100 80 100 100 100 2-296 80 100 90 90 100 100 100 100 1-385 80 90 90 90 90 100 100 100 1-297 80 90 100 100 80 100 100 100 2-86 80 80 100 90 100 100 100 90 1-298 80 100 100 100 90 100 100 100
TABLE-US-00058 Ex- ample Dosage No. [g/ha] ALOMY AVEFA DIGSA ECHCG SETVI 1-312 80 90 90 100 100 100 2-324 80 90 100 100 100 90 Ex- ample Dosage No. [g/ha] ABUTH AMARE MATIN PHBPU POLCO 1-312 80 100 100 100 100 100 2-324 80 100 100 100 100 100 Ex- ample Dosage No. [g/ha] STEME VIOTR VERPE HORMU 1-312 80 100 100 90 80 2-324 80 100 100 100 90
TABLE-US-00059 Ex- ample Dosage No. [g/ha] ALOMY AVEFA DIGSA ECHCG LOLRI 1-363 80 90 100 100 100 80 Ex- ample Dosage No. [g/ha] SETVI ABUTH AMARE MATIN PHBPU 1-363 80 100 100 100 100 90 Ex- ample Dosage No. [g/ha] STEME VIOTR VERPE HORMU 1-363 80 100 100 100 90
TABLE-US-00060 Ex- ample Dosage No. [g/ha] ALOMY AVEFA CYPES ECHCG SETVI 3-314 80 100 100 80 100 100 Ex- ample Dosage No. [g/ha] ABUTH AMARE MATIN PHBPU POLCO 3-314 80 100 100 100 100 100 Ex- ample Dosage No. [g/ha] STEME VIOTR VERPE HORMU 3-314 80 100 100 100 90
TABLE-US-00061 Ex- ample Dosage No. [g/ha] ALOMY AVEFA ECHCG LOLRI SETVI 1-362 80 90 100 100 80 90 3-162 80 90 90 100 80 100 Ex- ample Dosage No. [g/ha] ABUTH AMARE MATIN PHBPU POLCO 1-362 80 100 100 100 100 90 3-162 80 100 100 100 90 100 Ex- ample Dosage No. [g/ha] STEME VIOTR VERPE HORMU 1-362 80 100 100 100 100 3-162 80 100 100 100 90
TABLE-US-00062 Ex- ample Dosage No. [g/h] ALOMY AVEFA CYPES ECHCG SETVI ABUTH AMARE 3-297 80 90 100 80 80 80 80 100 2-385 80 80 90 90 90 90 100 90 1-308 80 100 100 90 100 100 100 100 1-86 80 80 100 80 80 80 80 80 2-161 80 80 90 80 90 100 90 100 3-381 80 80 100 90 90 90 90 90 Ex- ample Dosage No. [g/h] MATIN PHBPU POLCO STEME VIOTR VERPE 3-297 80 100 90 80 100 100 100 2-385 80 100 80 90 100 100 100 1-308 80 100 100 90 100 90 80 1-86 80 100 90 80 100 100 90 2-161 80 100 90 100 100 100 100 3-381 80 90 100 80 100 100 100
TABLE-US-00063 Ex- ample Dosage No. [g/ha] ALOMY AVEFA ECHCG LOLMU SETVI ABUTH AMARE 1-383 80 100 90 90 90 90 100 90 2-383 80 80 100 90 80 100 100 100 2-322 80 80 80 100 80 100 100 80 2-384 80 90 90 90 80 90 100 90 1-380 80 90 100 90 100 90 90 80 2-380 80 80 100 90 80 100 80 80 2-381 80 80 100 90 80 100 90 90 1-322 80 90 80 100 90 100 100 80 2-297 80 100 100 100 90 100 80 100 Ex- ample Dosage No. [g/ha] MATIN PHBPU POLCO STEME VIOTR VERPE 1-383 80 90 90 90 100 100 100 2-383 80 100 90 90 90 100 100 2-322 80 90 90 100 100 100 90 2-384 80 100 90 80 100 100 100 1-380 80 90 90 90 100 100 100 2-380 80 100 90 90 100 100 100 2-381 80 90 100 90 100 100 100 1-322 80 80 80 90 100 100 100 2-297 80 100 100 90 100 100 100
TABLE-US-00064 Ex- ample Dosage No. [g/ha] ALOMY AVEFA CYPES ECHCG LOLMU SETVI ABUTH 1-559 80 90 100 90 100 100 100 90 1-296 80 100 90 90 100 90 100 100 1-84 80 80 90 80 90 80 100 90 Ex- ample Dosage No. [g/ha] AMARE MATIN PHBPU STEME VIOTR VERPE 1-559 80 100 100 100 100 100 100 1-296 80 100 100 100 100 100 100 1-84 80 90 100 100 100 100 100
TABLE-US-00065 Example Dosage No. [g/ha] ALOMY AVEFA ECHCG SETVI ABUTH AMARE MATIN PHBPU POLCO STEME VIOTR VERPE HORMU 2-163 80 90 100 100 90 100 100 100 90 90 100 100 100 80 3-163 80 90 90 90 90 100 90 90 90 90 100 100 100 80 2-363 80 90 90 100 90 100 100 100 90 100 100 100 100 90 2-311 80 90 90 100 100 90 100 100 90 90 100 100 100 80 3-311 80 100 100 100 80 100 100 100 100 80 100 90 80 90
TABLE-US-00066 Example Dosage No. [g/ha] ALOMY AVEFA CYPES ECHCG LOLMU SETVI ABUTH MATIN PHBPU POLCO STEME VIOTR VERPE 1-325 80 90 90 80 100 90 100 100 80 100 90 100 100 100
TABLE-US-00067 Example Dosage No. [g/ha] ALOMY AVEFA DIGSA ECHCG SETVI ABUTH AMARE MATIN PHBPU POLCO STEME VIOTR VERPE 1-306 80 90 80 100 90 90 90 100 90 90 90 90 100 90 1-316 80 90 100 100 100 90 100 100 90 90 100 100 100 100
TABLE-US-00068 Example Dosage No. [g/ha] AVEFA CYPES ECHCG LOLMU SETVI ABUTH AMARE MATIN PHBPU POLCO STEME VIOTR VERPE 1-85 80 80 80 90 80 100 90 90 100 100 80 100 100 100
TABLE-US-00069 Example Dosage No. [g/ha] ALOMY AVEFA CYPES ECHCG SETVI ABUTH AMARE MATIN PHBPU STEME VIOTR VERPE HORMU 1-311 80 100 100 100 100 100 100 100 100 100 100 100 100 100
TABLE-US-00070 Example Dosage No. [g/ha] ALOMY AVEFA CYPES ECHCG LOLMU SETVI ABUTH AMARE PHBPU POLCO STEME VIOTR VERPE 1-320 80 100 100 80 100 80 100 100 100 90 80 100 100 100 2-320 80 100 90 80 100 80 100 100 100 90 100 100 100 100
TABLE-US-00071 Example Dosage No. [g/ha] ALOMY DIGSA ECHCG SETVI ABUTH AMARE MATIN PHBPU POLCO STEME VIOTR VERPE 1-171 80 80 100 100 100 100 100 90 90 100 100 90 100 2-170 80 80 100 100 90 100 100 100 90 90 100 100 90
TABLE-US-00072 Example Dosage No. [g/ha] ALOMY AVEFA ECHCG SETVI ABUTH AMARE MATIN PHBPU POLCO STEME VIOTR VERPE 1-301 80 80 100 90 90 80 80 90 100 100 100 100 100 2-559 80 90 100 100 100 90 100 100 100 80 100 100 100 2-301 80 80 90 90 90 80 80 90 90 90 100 100 100 2-162 80 90 100 90 90 100 90 100 90 90 100 100 90 1-191 80 80 80 100 100 100 80 90 80 90 100 100 100 2-298 80 80 100 90 90 80 90 100 90 90 100 100 100 3-320 80 80 90 100 100 100 80 100 90 90 100 100 100 3-323 80 80 90 100 100 100 90 90 90 80 100 90 90 2-107 80 80 80 90 90 90 90 90 90 90 100 100 100 3-383 80 80 90 90 90 90 90 100 90 90 100 100 100 3-299 80 80 80 90 90 90 90 100 90 80 100 100 100 3-384 80 80 90 90 100 100 90 100 80 90 100 100 100 2-325 80 80 90 100 100 100 90 80 90 90 100 100 90 1-88 80 80 80 90 90 80 90 90 90 90 100 100 100 3-363 80 80 80 100 100 90 100 100 90 90 100 100 100
TABLE-US-00073 Example Dosage No. [g/ha] ALOMY AVEFA CYPES ECHCG SETVI ABUTH AMARE MATIN PHBPU STEME VIOTR VERPE 3-308 80 100 100 90 100 100 100 100 100 90 100 80 80 1-161 80 90 100 80 90 100 90 100 100 90 100 100 100
TABLE-US-00074 Example Dosage No. [g/ha] AVEFA DIGSA ECHCG SETVI ABUTH AMARE MATIN PHBPU POLCO STEME VIOTR BERPE 2-315 80 90 100 100 100 100 100 90 100 100 100 100 100 1-552 80 90 90 90 80 90 90 90 100 90 90 90 100
TABLE-US-00075 Example Dosage No. [g/ha] ALOMY ECHCG SETVI ABUTH AMARE MATIN PHBPU POLCO STEME VIOTR VERPE 2-382 80 80 90 90 100 90 100 100 80 100 100 100 2-287 80 100 100 90 80 90 100 90 80 100 100 80 2-288 80 80 90 90 90 100 90 90 90 100 80 100
TABLE-US-00076 Example Dosage No. [g/ha] AVEFA CYPES ECHCG SETVI ABUTH AMARE MATIN PHBPU STEME VIOTR VERPE 1-561 80 90 80 100 100 90 100 100 100 100 100 100 1-242 80 80 80 100 90 90 100 90 100 100 100 100
TABLE-US-00077 Example Dosage No. [g/ha] CYPES ECHCG SETVI ABUTH AMARE MATIN PHBPU POLCO STEME VIOTR VERPE 3-382 80 80 90 100 100 100 90 100 80 100 90 90
TABLE-US-00078 Example Dosage No. [g/ha] AVEFA ECHCG SETVI ABUTH AMARE MATIN PHBPU POLCO STEME VIOTR VERPE 3-298 80 100 90 80 80 100 100 100 90 100 100 100 1-107 80 80 90 90 80 90 90 80 90 100 100 100 3-107 80 80 90 90 80 90 90 80 90 80 100 100 1-134 80 90 100 100 100 100 100 100 90 100 100 100 2-135 80 100 100 100 100 100 100 100 90 100 100 100 3-134 80 90 100 100 100 100 100 100 90 100 100 100 3-88 80 80 90 90 80 80 90 90 90 100 100 90 1-382 80 100 90 90 100 100 100 100 90 100 100 100 3-161 80 90 90 100 100 100 90 90 80 100 100 100
TABLE-US-00079 Example Dosage No. [g/ha] ALOMY AVEFA ECHCG SETVI ABUTH AMARE MATIN PHBPU STEME VIOTR VERPE 3-296 80 80 90 100 90 100 100 100 90 100 100 100 2-88 80 90 90 90 90 80 90 90 90 100 100 100
TABLE-US-00080 Example Dosage No. [g/ha] ALOMY DIGSA ECHCG SETVI ABUTH AMARE MATIN POLCO STEME VIOTR VERPE 1-364 80 90 100 100 100 100 100 100 100 100 100 100
TABLE-US-00081 Example Dosage No. [g/ha] ALOMY CYPES ECHCG SETVI ABUTH AMARE MATIN PHBPU STEME VIOTR VERPE 1-288 80 80 90 90 100 90 100 100 90 100 100 100 2-37 80 80 80 100 100 80 90 80 80 100 100 100
TABLE-US-00082 Example Dosage No. [g/ha] DIGSA ECHCG SETVI ABUTH AMARE MATIN PHBPU POLCO STEME VIOTR VERPE 2-171 80 90 90 90 100 100 100 100 90 100 100 100
TABLE-US-00083 Example Dosage No. [g/ha] AVEFA DIGSA ECHCG ABUTH AMARE MATIN PHBPU POLCO STEME VIOTR VERPE 3-170 80 80 100 90 100 100 100 90 90 100 100 90
TABLE-US-00084 Example Dosage No. [g/ha] ALOMY AVEFA ECHCG SETVI ABUTH MATIN PHBPU POLCO STEME VIOTR VERPE 3-380 80 80 100 90 90 80 100 90 90 100 100 80
TABLE-US-00085 Example Dosage No. [g/ha] CYPES ECHCG SETVI ABUTH AMARE MATIN PHBPU STEME VIOTR VERPE 1-109 80 80 100 90 90 100 100 100 100 100 100 1-39 80 80 80 90 90 90 90 80 80 90 90 2-39 80 80 90 100 90 100 80 90 100 100 100
TABLE-US-00086 Example Dosage No. [g/ha] AVEFA CYPES ECHCG SETVI ABUTH PHBPU POLCO STEME VIOTR HORMU 3-324 80 100 90 100 100 100 100 100 100 100 80
TABLE-US-00087 Example Dosage No. [g/ha] DIGSA ECHCG ABUTH AMARE MATIN PHBPU POLCO STEME VIOTR VERPE 3-171 80 90 90 100 100 90 90 90 100 100 100 3-172 80 90 90 100 100 90 100 80 100 90 100
TABLE-US-00088 Example Dosage No. [g/ha] ALOMY ECHCG SETVI ABUTH AMARE MATIN PHBPU STEME VIOTR VERPE 2-108 80 80 100 90 100 100 100 100 100 100 100
TABLE-US-00089 Example Dosage No. [g/ha] ALOMY AVEFA ECHCG SETVI ABUTH AMARE MATIN STEME VIOTR VERPE 1-287 80 90 80 100 90 100 100 100 100 100 100
TABLE-US-00090 Example Dosage No. [g/ha] AVEFA ECHCG SETVI ABUTH MATIN PHBPU POLCO STEME VIOTR VERPE 3-86 80 80 90 90 80 90 90 80 100 100 80 3-301 80 90 90 90 80 100 100 100 100 100 80
TABLE-US-00091 Example Dosage No. [g/ha] AVEFA ECHCG SETVI ABUTH AMARE MATIN PHBPU STEME VIOTR VERPE 1-182 80 80 90 90 90 90 90 90 100 100 100 2-136 80 100 100 100 100 100 100 90 100 100 100 3-37 80 80 100 90 80 100 90 80 100 100 100 3-39 80 80 90 90 90 100 80 90 90 100 100
TABLE-US-00092 Example Dosage No. [g/ha] ECHCG SETVI ABUTH AMARE MATIN PHBPU POLCO STEME VIOTR VERPE 3-385 80 100 90 100 90 90 90 90 100 100 100
TABLE-US-00093 Example Dosage No. [g/ha] AVEFA ECHCG SETVI ABUTH AMARE MATIN PHBPU POLCO STEME VIOTR 3-135 80 100 100 100 100 100 100 90 100 100 100
TABLE-US-00094 Example Dosage No. [g/ha] ALOMY ECHCG SETVI ABUTH AMARE PHBPU POLCO STEME VIOTR VERPE 3-136 80 90 100 100 100 100 90 80 100 100 100
TABLE-US-00095 Example Dosage No. [g/ha] AVEFA ECHCG SETVI ABUTH AMARE MATIN PHBPU POLCO STEME VERPE 3-322 80 80 100 80 100 90 90 90 80 100 80
TABLE-US-00096 Example Dosage No. [g/ha] AVEFA ECHCG SETVI ABUTH AMARE MATIN PHBPU STEME VIOTR VERPE 1-243 80 80 100 100 90 90 100 100 100 100 100
TABLE-US-00097 Example Dosage No. [g/ha] ECHCG SETVI ABUTH AMARE MATIN PHBPU STEME VIOTR VERPE 1-571 80 90 80 80 80 80 90 100 80 90 1-244 80 90 100 90 90 100 100 100 100 100 1-108 80 80 80 80 100 100 90 100 100 100 1-37 80 100 100 90 100 80 90 100 100 100 1-135 80 90 100 90 100 100 90 90 90 100
TABLE-US-00098 Example Dosage No. [g/ha] AVEFA ECHCG ABUTH AMARE MATIN PHBPU STEME VIOTR VERPE 2-278 80 100 100 90 90 90 80 80 100 100
TABLE-US-00099 Example Dosage No. [g/ha] AVEFA CYPES ECHCG SETVI ABUTH PHBPU STEME VIOTR HORMU 3-325 80 100 90 100 100 100 90 100 100 90
TABLE-US-00100 Example Dosage No. [g/ha] ALOMY ECHCG SETVI AMARE MATIN PHBPU STEME VIOTR VERPE 1-289 80 80 100 90 100 100 90 100 100 100
TABLE-US-00101 Example Dosage No. [g/ha] ECHCG SETVI AMARE MATIN PHBPU POLCO STEME VIOTR VERPE 2-289 80 100 100 100 100 90 80 100 80 90 1-134 80 90 100 100 100 90 80 90 100 100
TABLE-US-00102 Example Dosage No. [g/ha] AVEFA ECHCG AMARE MATIN PHBPU STEME VIOTR VERPE 3-108 80 80 80 80 90 100 100 100 100
TABLE-US-00103 Example Dosage No. [g/ha] ECHCG SETVI AMARE MATIN PHBPU STEME VIOTR VERPE 3-109 80 90 90 100 100 90 100 100 100 1-136 80 90 90 90 90 90 100 90 100
TABLE-US-00104 Example Dosage No. [g/ha] AVEFA ECHCG SETVI AMARE PHBPU STEME VIOTR VERPE 2-280 80 90 90 80 90 90 100 90 80
TABLE-US-00105 Example Dosage No. [g/ha] ECHCG ABUTH AMARE PHBPU POLCO STEME VIOTR VERPE 1-229 80 90 100 80 80 80 100 90 90
TABLE-US-00106 Example Dosage No. [g/ha] SETVI ABUTH AMARE MATIN PHBPU STEME VIOTR VERPE 1-313 80 80 100 90 90 90 100 80 80
TABLE-US-00107 Example Dosage No. [g/ha] ECHCG SETVI ABUTH AMARE MATIN STEME VIOTR VERPE 3-38 80 90 80 90 100 80 100 100 100
TABLE-US-00108 Example Dosage No. [g/ha] ECHCG SETVI ABUTH AMARE MATIN PHBPU STEME VERPE 1-570 80 100 80 90 90 90 90 80 90
TABLE-US-00109 Example Dosage No. [g/ha] ECHCG ABUTH AMARE MATIN PHBPU STEME VIOTR VERPE 3-199 80 80 90 80 80 90 80 90 100
TABLE-US-00110 Example Dosage No. [g/ha] ECHCG SETVI ABUTH AMARE PHBPU STEME VIOTR 1-278 80 100 100 90 100 90 90 100
TABLE-US-00111 Example Dosage No. [g/ha] ECHCG SETVI ABUTH AMARE PHBPU VIOTR VERPE 1-572 80 90 80 80 90 80 80 90
TABLE-US-00112 Example Dosage No. [g/ha] ECHCG ABUTH AMARE MATIN PHBPU STEME VIOTR 3-287 80 90 90 100 100 80 100 90
TABLE-US-00113 Example Dosage No. [g/ha] ECHCG ABUTH AMARE PHBPU STEME VIOTR VERPE 1-199 80 80 90 80 80 90 90 80
TABLE-US-00114 Example Dosage No. [g/ha] ECHCG SETVI ABUTH AMARE MATIN PHBPU 2-362 80 100 90 90 100 100 90
TABLE-US-00115 Example Dosage No. [g/ha] ECHCG ABUTH AMARE MATIN STEME VERPE 3-289 80 90 80 90 100 90 90
TABLE-US-00116 Example Dosage No. [g/ha] ECHCG AMARE PHBPU STEME VIOTR 1-280 80 90 90 90 100 90
TABLE-US-00117 Example Dosage No. [g/ha] ECHCG AMARE STEME VIOTR VERPE 1-38 80 90 100 100 80 90
TABLE-US-00118 Example Dosage No. [g/ha] ECHCG ABUTH AMARE MATIN 3-362 80 80 80 80 90
[0647] Comparative Experiments
[0648] In the experiments that follow, herbicidal action of numerous inventive compounds and the known compounds that are structurally closest from D1 (WO 2012/028579 A1) and D2 (WO 2018/202535 A1) were compared under the above-specified conditions by the pre-emergence and post-emergence method. The example numbers given in the tables relate to the compounds disclosed in the respective documents. In addition to the compounds disclosed in D1 and D2, the following compounds V-1 to V-14 that are encompassed by D1 or D2 but are not compounds specified therein were used in the comparative experiments:
[0649] V-1: 2-(methylsulfanyl)-3-(methylsulfinyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide
[0650] V-2: 2-(methylsulfanyl)-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide
[0651] V-3: 2,3-bis(ethylsulfanyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide
[0652] V-4: 2-chloro-3-(ethylsulfanyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide
[0653] V-5: 2-chloro-4-iodo-3-(methylsulfanyl)-N-(1-methyl-1H-tetrazol-5-yl)benzamide
[0654] V-6: 2-chloro-4-iodo-3-(methylsulfinyl)-N-(1-methyl-1H-tetrazol-5-yl)benzamide
[0655] V-7: 2-chloro-4-iodo-3-(methylsulfonyl)-N-(1-methy1-1H-tetrazol-5-yl)benzamide
[0656] V-8: 2-bromo-3-(methylsulfanyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide
[0657] V-9: 2-bromo-3-(methylsulfinyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide
[0658] V-10: 2-bromo-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide
[0659] V-11: 2-bromo-3-(ethylsulfanyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide
[0660] V-12: 2-bromo-3-(ethylsulfinyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide
[0661] V-13: 2-bromo-3-(ethylsulfonyl)-N-(1-methyl-1-1 H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide
[0662] V-14: 2-cyclopropyl-3-(ethylsulfanyl)-N-(1-methyl-1H-tetrazol-5-yl) -4-(trifluoromethyl)benzamide
[0663] Herbicidal Pre-Emergence Action:
TABLE-US-00119 Dosage (g of Herbicidal action against Example No.: a.i./ha) AVEFA MATIN PHBPU STEME VIOTR VERPE 1-46, inventive 20 20 80 40 90 70 50 4-108 from D1 20 0 0 40 70 20 30
TABLE-US-00120 Example Dosage Herbicidal action against No.: (g of a.i./ha) AMARE VIOTR 1-47, inventive 20 80 30 4-109 from D1 20 20 10
TABLE-US-00121 Example Dosage Herbicidal action against No.: (g of a.i./ha) CYPES ECHCG POLCO 1-163, inventive 20 70 90 70 V-2 from D1 20 0 50 0
TABLE-US-00122 Example Dosage Herbicidal action against No.: (g of a.i./ha) CYPES PHBPU POLCO 1-134, inventive 20 50 20 30 4-312 from D1 20 0 0 0
TABLE-US-00123 Dosage (g of Herbicidal action against Example No.: a.i./ha) CYPES ECHCG ABUTH AMARE PHBPU POLCO 1-162, inventive 20 70 90 100 100 60 80 V-1 from D1 20 50 50 0 60 0 0
TABLE-US-00124 Dosage (g of Herbicidal action against Example No.: a.i./ha) ECHCG AMARE MATIN STEME VIOTR VERPE 1-182, inventive 20 80 70 80 90 80 90 V-3 from D1 20 0 0 0 0 0 0
TABLE-US-00125 Example Dosage Herbicidal action against No.: (g of a.i./ha) CYPES LOLMU MATIN 1-297, inventive 20 100 30 100 4-639 from D1 20 60 10 60
TABLE-US-00126 Example Dosage Herbicidal action against No.: (g of a.i./ha) CYPES 1-298, inventive 20 100 4-640 from D1 20 0
TABLE-US-00127 Dosage (g of Herbicidal action against Example No.: a.i./ha) ALOMY CYPES SETVI ABUTH MATIN VERPE 1-299, inventive 20 80 90 90 90 90 100 V-4 from D1 20 40 0 60 0 50 80
TABLE-US-00128 Dosage (g of Herbicidal action against Example No.: a.i./ha) CYPES ECHCG SETVI AMARE MATIN STEME VERPE 1-362, inventive 20 80 80 90 90 70 90 60 V-5 from D1 20 0 0 0 70 20 0 0
TABLE-US-00129 Dosage (g of Herbicidal action against Example No.: a.i./ha) ALOMY SETVI ABUTH AMARE MATIN STEME 1-363, inventive 20 50 90 100 100 90 100 V-6 from D1 20 30 60 40 50 60 0
TABLE-US-00130 Dosage (g of Herbicidal action against Example No.: a.i./ha) ECHCG SETVI AMARE POLCO STEME VERPE 1-364, inventive 20 90 100 100 90 90 100 V-7 from D1 20 10 0 30 0 0 40
TABLE-US-00131 Example Dosage Herbicidal action against No.: (g of a.i./ha) CYPES 1-380, inventive 20 60 V-8 from D1 20 0
TABLE-US-00132 Example Dosage Herbicidal action against No.: (g of a.i./ha) ALOMY VERPE 1-382, inventive 20 30 100 V-10 from D1 20 10 60
TABLE-US-00133 Example Dosage Herbicidal action against No.: (g of a.i./ha) ALOMY ECHCG SETVI STEME VIOTR 1-381, 20 50 90 80 90 90 inventive V-9 20 20 60 40 60 70 from D1
TABLE-US-00134 Dosage Herbicidal action against Example No.: (g of a.i./ha) CYPES ECHCG SETVI ABUTH AMARE VIOTR VERPE 1-383, inventive 80 100 100 100 100 100 100 100 V-11 from D1 80 0 0 0 0 0 80 10
TABLE-US-00135 Dosage Herbicidal action against Example No.: (g of a.i./ha) ALOMY CYPES ECHCG SETVI ABUTH STEME VIOTR 1-384, inventive 80 100 100 100 100 100 100 100 V-12 from D1 80 0 0 0 0 0 0 0
TABLE-US-00136 Dosage Herbicidal action against Example No.: (g of a.i./ha) ALOMY ECHCG SETVI ABUTH AMARE MATIN VERPE 1-385, inventive 80 100 100 90 100 100 100 100 V-13 from D1 80 0 0 0 0 0 0 0
TABLE-US-00137 Dosage Herbicidal action against Example (g of No.: a.i./ha) AVEFA CYPES ECHCG ABUTH STEME 1-320, 20 70 80 100 90 90 inventive 1-49 from D1 20 50 50 50 70 30
TABLE-US-00138 Example Dosage Herbicidal action against No.: (g of a.i./ha) PHBPU 1-517, inventive 20 60 V-1 from D1 20 0
TABLE-US-00139 Dosage Herbicidal (g of action against Example No.: a.i./ha) VIOTR 1-570, inventive 20 70 4-321 from D1 20 20
[0664] Herbicidal Post-Emergence Action:
TABLE-US-00140 Dosage Herbicidal action against Example No.: (g of a.i./ha) ECHCG SETVI ABUTH AMARE STEME VIOTR VERPE 1-182, inventive 5 80 70 70 80 90 90 100 V-3 from D1 5 0 0 0 0 0 0 0
TABLE-US-00141 Dosage Herbicidal (g of action against Example No.: a.i./ha) POLCO 1-163, inventive 5 70 V-2 from D1 5 0
TABLE-US-00142 Dosage (g of Herbicidal action against Example No.: a.i./ha) MATIN VIOTR VERPE 1-134, inventive 5 90 100 100 4-312 from D1 5 70 50 80
TABLE-US-00143 Dosage Herbicidal action against Example No.: (g of a.i./ha) AMARE VIOTR 1-296, inventive 5 60 100 4-638 from D1 5 20 40
TABLE-US-00144 Dosage Herbicidal action against Example No.: (g of a.i./ha) CYPES PHBPU 1-297, inventive 5 60 80 4-639 from D1 5 30 20
TABLE-US-00145 Dosage Herbicidal action against Example No.: (g of a.i./ha) ALOMY AVEFA CYPES AMARE MATIN POLCO VERPE 1-298, inventive 5 70 60 60 100 100 60 90 4-640 from D1 5 20 30 20 80 30 20 70
TABLE-US-00146 Dosage Herbicidal action against Example No.: (g of a.i./ha) ALOMY AVEFA LOLMU MATIN POLCO STEME VERPE 1-299, inventive 5 70 80 70 80 60 100 100 V-4 from D1 5 40 30 10 60 30 60 80
TABLE-US-00147 Dosage Herbicidal action against Example No.: (g of a.i./ha) ALOMY CYPES AMARE STEME 1-362, inventive 5 70 30 100 90 V-5 from D1 5 40 10 70 10
TABLE-US-00148 Dosage Herbicidal action against Example No.: (g of a.i./ha) ALOMY AVEFA SETVI ABUTH STEME VIOTR VERPE 1-383, inventive 20 80 90 90 90 100 100 100 V-11 from D1 20 0 0 0 0 0 20 40
TABLE-US-00149 Dosage Herbicidal action against Example No.: (g of a.i./ha) ECHCG SETVI ABUTH AMARE MATIN VIOTR VERPE 1-384, inventive 20 90 90 90 90 90 100 100 V-12 from D1 20 0 20 0 10 0 0 0
TABLE-US-00150 Dosage Herbicidal action against Example No.: (g of a.i./ha) AMARE MATIN PHBPU POLCO STEME VIOTR VERPE 1-385, inventive 20 90 90 80 70 100 100 100 V-13 from D1 20 0 0 0 0 0 0 0
TABLE-US-00151 Dosage Herbicidal action against Example No.: (g of a.i./ha) ALOMY AVEFA CYPES ECHCG LOLMU SETVI 1-385, inventive 20 80 80 60 90 50 90 V-13 from D1 20 0 0 0 0 0 0
TABLE-US-00152 Dosage Herbicidal action against Example No.: (g of a.i./ha) CYPES POLCO VIOTR 1-570, inventive 5 60 30 60 4-321 from D1 5 0 0 40
TABLE-US-00153 Dosage Herbicidal action Example No.: (g of a.i./ha) against VIOTR 1-572, inventive 5 50 4-323 from D1 5 0
TABLE-US-00154 Dosage Herbicidal action Example No.: (g of a.i./ha) against ECHCG 1-107, inventive 5 80 1-1 from D2 5 40
TABLE-US-00155 Dosage Herbicidal action Example No.: (g of a.i./ha) against AMARE 1-109, inventive 5 100 1-3 from D2 5 60
TABLE-US-00156 Dosage Herbicidal action against Example No.: (g of a.i./ha) AVEFA SETVI 1-323, inventive 5 70 100 1-52 from D2 5 50 60
TABLE-US-00157 Dosage Herbicidal action against Example No.: (g of a.i./ha) ECHCG SETVI ABUTH AMARE STEME VERPE 1-320, inventive 5 100 100 100 100 100 100 1-49 from D2 5 80 80 70 70 70 70