SUBSTITUTED ISOPHTHALIC ACID DIAMIDES AND THEIR USE AS HERBICIDES

Abstract

There are described isophthalamides of the general formula (I) as herbicides.

##STR00001##

In this formula (I) X and Y are radicals such as hydrogen, alkyl and halogen. Z.sup.1 and Z.sup.2 are radicals such as alkyl, cycloalkyl and phenyl. Q is a heterocyclic ring such as tetrazolyl.

Claims

1. An isophthalamide of formula (I) or salt thereof ##STR00027## in which the symbols and indices are defined as follows: Q is Q.sup.1 or Q.sup.2, ##STR00028## W is nitrogen, 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, R.sup.1O—(C.sub.1-C.sub.6)-alkyl or R.sup.2S(O).sub.n—(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, with the proviso that Y is not methylsulfonyl when X is chlorine, Z.sup.1, Z.sup.2 are independently one of the following groups, each of which is substituted by s radicals from the group consisting of halogen, cyano, R.sup.1C(O), R.sup.1OC(O), R.sup.1O and R.sup.2(O).sub.nS:(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.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkenyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.2-C.sub.6)-alkynyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy, R.sup.2S(O).sub.n—(C.sub.1-C.sub.6)-alkyl, R.sup.1C(O), R.sup.1OC(O), R.sup.1C(O)—(C.sub.1-C.sub.6)-alkyl, R.sup.1OC(O)—(C.sub.1-C.sub.6)-alkyl, R.sup.1NH—(C.sub.1-C.sub.6)-alkyl, R.sup.1.sub.2N—(C.sub.1-C.sub.6)-alkyl, R.sup.1NHC(O)—(C.sub.1-C.sub.6)-alkyl or R.sup.1.sub.2NC(O)—(C.sub.1-C.sub.6)-alkyl, or one of the following groups, each substituted by s radicals from the group consisting of halogen, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy, halo-(C.sub.1-C.sub.6)-alkoxy, R.sup.1C(O) and R.sup.1OC(O): phenyl, benzyl, heterocyclyl or heterocyclyl-(C.sub.1-C.sub.6)-alkyl, or Z.sup.1 and Z.sup.2, together with the nitrogen atom to which they are bonded, form a four-, five-, six- or seven-membered heterocycle which contains n further heteroatoms from the group of O, S and N as ring members and which is substituted by m radicals from the group consisting of carbonyl, halogen, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy and halo-(C.sub.1-C.sub.6)-alkoxy, R.sup.1 is (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl, R.sup.2 is (C.sub.1-C.sub.6)-alkyl, R.sup.x is (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl or phenyl, m is 0, 1, 2 or 3, n is 0, 1 or 2, s is 0, 1, 2, 3 or 4.

2. An isophthalamide or salt as claimed in claim 1, in which Q is Q.sup.1 or Q.sup.2, R.sup.x is Me, Et, Pr, i-Pr, c-Pr, (CH.sub.2).sub.2OMe or Ph, W is nitrogen, X is halogen, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, cPr, OMe, OEt, SMe, SEt, CH.sub.2OMe or CH.sub.2SMe, Y is halogen, halo-(C.sub.1-C.sub.6)-alkyl, OMe, SMe, S(O)Me, SO.sub.2Me, SEt, S(O)Et or SO.sub.2Et, with the proviso that Y is not methylsulfonyl when X is chlorine, Z.sup.1, Z.sup.2 are independently (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, CH.sub.2cPr, halo-(C.sub.1-C.sub.6)-alkyl, (CH.sub.2).sub.2OMe, (CH.sub.2).sub.2SMe, allyl, propynyl, C(O)CH.sub.3, C(O)-c-Pr, CO.sub.2Me, CO.sub.2Et, Ph, (2-Me)Ph, (4-F)Ph, CH.sub.2C(O)NMe.sub.2, CH.sub.2C(O)Me or CH.sub.2C(O)cPr, or Z.sup.1 and Z.sup.2 together are (CH.sub.2).sub.3 or (CH.sub.2).sub.4, or W, Z.sup.1 and Z.sup.2 together are pyrazol-1-yl or L-prolin-1-yl ethyl ester.

3. An isophthalamide or salt as claimed in claim 1, in which Q is Q.sup.1 or Q.sup.2, R.sup.x is Me, Et or Pr, W is nitrogen, X is F, Cl, Br, I, Me, Et, c-Pr, OMe, SMe, SEt or CH.sub.2OMe, Y is F, Cl, Br, I, SMe, S(O)Me, SO.sub.2Me, CHF.sub.2, CF.sub.3 or C.sub.2F.sub.5, with the proviso that Y is not methylsulfonyl when X is chlorine, Z.sup.1, Z.sup.2 are independently Me, Et, c-Pr, CH.sub.2-c-Pr, CH.sub.2CHF.sub.2, CH.sub.2CF.sub.3, C(O)CH.sub.3, C(O)-c-Pr, CO.sub.2Me, CO.sub.2Et, Ph or (2-Me)Ph, or Z.sup.1 and Z.sup.2 together are (CH.sub.2).sub.4, or W, Z.sup.1 and Z.sup.2 together are pyrazol-1-yl or L-prolin-1-yl ethyl ester, R.sup.1 is Me, Et or c-Pr, R.sup.2 is Me.

4. A herbicidal composition or plant growth-regulating composition, comprising one or more isophthalamides 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 dichlormid.

9. A method of controlling one or more unwanted plants, comprising applying an effective amount of at least one isophthalamide of the formula (I) or salt as claimed in claim 1 or a herbicidal composition thereof to the plants and/or to a site of unwanted vegetation.

10. A product comprising a compound of formula (I) or salt as claimed in claim 1 or a herbicidal composition thereof for controlling one or more unwanted plants.

11. The product as claimed in claim 10, wherein the isophthalamide of formula (I) or salt is for controlling one or more unwanted plants in one or more crops of one or more useful plants.

12. The product as claimed in claim 11, wherein the useful plants are transgenic useful plants.

Description

[0395] The examples which follow illustrate the invention.

A. Chemical Examples

Synthesis of N.SUP.3.-ethyl-N.SUP.3.-2-dimethyl-N.SUP.1.-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)isophthalamide

Example No. 1-20

Step 1: Preparation of 3-(methoxycarbonyl)-2-methyl-6-(trifluoromethyl)benzoic acid

[0396] To an initial charge of 15 g (43.5 mmol) of methyl 3-iodo-2-methyl-4-(trifluoromethyl)benzoate in 400 ml of dry THF was added, at −70° C. within 60 min, 43.6 ml (56.6 mmol) of a 1.3 molar solution of i-PrMgCl/LiCl in THF. The reaction solution was warmed to −30° C. and stirred at that temperature for a further 60 min. Thereafter, it was cooled back down to −70° C., and gaseous CO.sub.2 was introduced. Thereafter—with continued introduction of CO.sub.2 and monitoring of the reaction—the mixture was warmed to room temperature. After the conversion had ended, the reaction solution was degassed in an ultrasound bath and then concentrated to dryness. The residue was taken up with water, adjusted to pH 3-4 with 2 N HCl, and extracted with dichloromethane. The organic phases were dried and concentrated. The residue was purified by column chromatography (HPLC, normal phase, gradient: ethyl acetate/n-heptane: 5%.fwdarw.70% ethyl acetate). 9 g of 3-(methoxycarbonyl)-2-methyl-6-(trifluoromethyl)benzoic acid was obtained.

[0397] .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=14.08 (br s, 1H); 7.94 (d, 1H); 7.77 (d, 1H); 3.89 (s, 3H); 2.46 (s, 3H).

Step 2: Preparation of methyl 3-[ethyl(methyl)carbamoyl]-2-methyl-4-(trifluoromethyl)benzoate

[0398] To an initial charge of 400 mg (1.52 mmol) of 3-(methoxycarbonyl)-2-methyl-6-(trifluoromethyl)benzoic acid in 20 ml dichloromethane were added a few drops of dimethylformamide. Thereafter, at room temperature, 0.2 ml (2.28 mmol) of oxalyl chloride was added and the reaction mixture was stirred at room temperature for 2 h. After the mixture had been concentrated, it was coevaporated twice with toluene. The residue was dissolved in 5 ml of dichloromethane and, at 0° C., added dropwise to a solution of 0.2 ml (2.28 mmol) of N-methylethanamine and 0.5 ml (3.05 mmol) of Hünig's base in 10 ml of dichloromethane. The reaction mixture was stirred at room temperature for 12 h and then concentrated to dryness. The residue was purified by column chromatography (HPLC, normal phase, gradient: ethyl acetate/n-heptane: 10%.fwdarw.70% ethyl acetate). 424 mg of methyl 3-[ethyl(methyl)carbamoyl]-2-methyl-4-(trifluoromethyl)benzoate was obtained.

[0399] .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=7.93 (d, 1H); 7.77 (d, 1H); 3.89 (s, 3H); 3.59 (m, 1H, isomer 1), 3.43 (m, 1H, isomer 1); 3.06 (m, 1H); isomer 2); 2.99 (s, 3H, isomer 1); 2.98 (m, 1H, isomer 2); 2.66 (s, 3H, isomer 2); 2.36 (s, 3H); 1.13 (t, 3H, isomer 1); 0.99 (t, 3H, isomer 2).

Step 3: Preparation of 3-[ethyl(methyl)carbamoyl]-2-methyl-4-(trifluoromethyl)benzoic acid

[0400] To an initial charge of 424 mg (1.39 mmol) of methyl 3-[ethyl(methyl)carbamoyl]-2-methyl-4-(trifluoromethyl)benzoate in 10 ml of methanol was added dropwise, at room temperature, a solution of 89 mg (2.09 mmol) of sodium hydroxide in 3 ml of water. The reaction mixture was stirred at room temperature for 4 h. Thereafter, the reaction mixture was concentrated to dryness, and the residue was taken up in 20 ml of water. The mixture was adjusted to pH 3-4 with 2N HCl, and the precipitate formed was filtered off and dried. 352 mg of 3-[ethyl(methyl)carbamoyl]-2-methyl-4-(trifluoromethyl)benzoic acid was obtained. .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=13.58 (br s, 1H); 7.90 (m, 1H); 7.73 (d, 1H); 3.60 (m, 1H), isomer 1); 3.42 (m, 1H, isomer 1); 3.05 (m, 1H), isomer 2); 3.00 (s, 3H, isomer 1); 2.98 (m, 1H, isomer 2); 2.66 (s, 3H, isomer 2); 1.13 (t, 3H, isomer 1); 0.99 (t, 3H, isomer 2).

Step 4: Preparation of N.SUP.3.-ethyl-N.SUP.3.-2-dimethyl-N.SUP.1.-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)isophthalamide

[0401] To an initial charge of 200 mg (0.69 mmol) of 3-[ethyl(methyl)carbamoyl]-2-methyl-4-(trifluoromethyl)benzoic acid in 3 ml of pyridine together with 104.9 mg (1.03 mmol) of 1-methyl-1H-tetrazole-5-amine at room temperature was added 0.09 ml (1.03 mmol) of oxalyl chloride. The reaction mixture was stirred at room temperature for 12 h. Then 10 ml of water was added and the mixture was extracted with dichloromethane. The organic phases were dried and concentrated to dryness. The residue was purified by column chromatography (HPLC, C.sub.18, gradient: acetonitrile/water (++0.05% trifluoroacetic acid), 20/80.fwdarw.100/0 in 30 min). 44 mg (along with mixed fractions) of N.sup.3-ethyl-N.sup.3, 2-dimethyl-N.sup.1-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)isophthalamide (Example No. 1-20) was obtained.

[0402] 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.

[0403] The abbreviations used here mean:

[0404] Me=methyl Bu=butyl Et=ethyl Pr=propyl c=cyclo Ph=phenyl

TABLE-US-00001 TABLE 1 Inventive compounds of the general formula (I) in which Q is Q.sup.1 and R.sup.x is methyl, and the other substituents have the definitions given below. [00018] embedded image No. X Y W Z.sup.1 Z.sup.2 1-1 Me F N Me Me 1-2 Me F N Me Et 1-3 Me F N Me c-Pr 1-4 Me Cl N Me Me 1-5 Me Cl N Me Et 1-6 Me Cl N Me c-Pr 1-7 Me Br N Me Me 1-8 Me Br N Me Et 1-9 Me Br N Me c-Pr 1-10 Me I N Me Me 1-11 Me I N Me Et 1-12 Me I N Me c-Pr 1-13 Me SMe N Me Me 1-14 Me SMe N Me Et 1-15 Me SMe N Me c-Pr 1-16 Me S(O)Me N Me Me 1-17 Me S(O)Me N Me Et 1-18 Me S(O)Me N Me c-Pr 1-19 Me CF.sub.3 N Me Me 1-20 Me CF.sub.3 N Me Et 1-21 Me CF.sub.3 N Me c-Pr 1-22 Me CF.sub.3 N Me CH.sub.2-c-Pr 1-23 Me CF.sub.3 N Me CH.sub.2CF.sub.3 1-24 Me CF.sub.3 N Me CH.sub.2CHF.sub.2 1-25 Me CF.sub.3 N Me C(O)CH.sub.3 1-26 Me CF.sub.3 N Me C(O)c-Pr 1-27 Me CF.sub.3 N Me C(O)OMe 1-28 Me CF.sub.3 N Me C(O)OEt 1-29 Me CF.sub.3 N Me Ph 1-30 Me CF.sub.3 N Me (2-Me)Ph 1-31 Me CF.sub.3 N Et Et 1-32 Me CF.sub.3 N Et c-Pr 1-33 Me CF.sub.3 N Et CH.sub.2-c-Pr 1-34 Me CF.sub.3 N Et CH.sub.2CF.sub.3 1-35 Me CF.sub.3 N Et CH.sub.2CHF.sub.2 1-36 Me CF.sub.3 N Et C(O)CH.sub.3 1-37 Me CF.sub.3 N Et C(O)c-Pr 1-38 Me CF.sub.3 N Et C(O)OMe 1-39 Me CF.sub.3 N Et C(O)OEt 1-40 Me CF.sub.3 N c-Pr c-Pr 1-41 Me CF.sub.3 N c-Pr CH.sub.2-c-Pr 1-42 Me CF.sub.3 N c-Pr CH.sub.2CF.sub.3 1-43 Me CF.sub.3 N c-Pr CH.sub.2CHF.sub.2 1-44 Me CF.sub.3 N c-Pr C(O)CH.sub.3 1-45 Me CF.sub.3 N c-Pr C(O)c-Pr 1-46 Me CF.sub.3 N c-Pr C(O)OMe 1-47 Me CF.sub.3 N c-Pr C(O)OEt 1-48 Me CF.sub.3 N —(CH.sub.2).sub.4— 1-49 Me CF.sub.3 Pyrazol-1-yl 1-50 Me CHF.sub.2 N Me Me 1-51 Me CHF.sub.2 N Me Et 1-52 Me CHF.sub.2 N Me c-Pr 1-53 Me CHF.sub.2 N Me CH.sub.2-c-Pr 1-54 Me CHF.sub.2 N Me CH.sub.2CF.sub.3 1-55 Me CHF.sub.2 N Me CH.sub.2CHF.sub.2 1-56 Me CHF.sub.2 N Me C(O)CH.sub.3 1-57 Me CHF.sub.2 N Me C(O)c-Pr 1-58 Me CHF.sub.2 N Me C(O)OMe 1-59 Me CHF.sub.2 N Et Et 1-60 Me CHF.sub.2 N Et c-Pr 1-71 Me CHF.sub.2 N Et CH.sub.2-c-Pr 1-72 Me CHF.sub.2 N Et CH.sub.2CF.sub.3 1-73 Me CHF.sub.2 N Et CH.sub.2CHF.sub.2 1-74 Me CHF.sub.2 N Et C(O)CH.sub.3 1-75 Me CHF.sub.2 N Et C(O)c-Pr 1-76 Me CHF.sub.2 N Et C(O)OMe 1-77 Me CHF.sub.2 N c-Pr c-Pr 1-78 Me CHF.sub.2 N c-Pr CH.sub.2-c-Pr 1-79 Me CHF.sub.2 N c-Pr CH.sub.2CF.sub.3 1-80 Me CHF.sub.2 N c-Pr CH.sub.2CHF.sub.2 1-81 Me CHF.sub.2 N c-Pr C(O)CH.sub.3 1-82 Me CHF.sub.2 N c-Pr C(O)c-Pr 1-83 Me CHF.sub.2 N c-Pr C(O)OMe 1-84 Me C.sub.2F.sub.5 N Me Me 1-85 Me C.sub.2F.sub.5 N Me Et 1-86 Me C.sub.2F.sub.5 N Me c-Pr 1-87 OMe Cl N Me Me 1-88 OMe Cl N Me Et 1-89 OMe Cl N Me c-Pr 1-90 OMe CF.sub.3 N Me Me 1-91 OMe CF.sub.3 N Me Et 1-92 OMe CF.sub.3 N Me c-Pr 1-93 OMe CHF.sub.2 N Me Me 1-94 OMe CHF.sub.2 N Me Et 1-95 OMe CHF.sub.2 N Me c-Pr 1-96 SMe SO.sub.2Me N Me Me 1-97 SMe SO.sub.2Me N Me Et 1-98 SMe SO.sub.2Me N Me c-Pr 1-99 SMe CF.sub.3 N Me Me 1-100 SMe CF.sub.3 N Me Et 1-101 SMe CF.sub.3 N Me c-Pr 1-102 SMe CHF.sub.2 N Me Me 1-103 SMe CHF.sub.2 N Me Et 1-104 SMe CHF.sub.2 N Me c-Pr 1-105 SEt CF.sub.3 N Me Me 1-106 SEt CF.sub.3 N Me Et 1-107 SEt CF.sub.3 N Me c-Pr 1-108 SEt CHF.sub.2 N Me Me 1-109 SEt CHF.sub.2 N Me Et 1-110 SEt CHF.sub.2 N Me c-Pr 1-111 F CF.sub.3 N Me Me 1-112 F CF.sub.3 N Me Et 1-113 F CF.sub.3 N Me c-Pr 1-114 F CHF.sub.2 N Me Me 1-115 F CHF.sub.2 N Me Et 1-116 F CHF.sub.2 N Me c-Pr 1-117 Cl SMe N Me Me 1-118 Cl SMe N Me Et 1-119 Cl SMe N Me c-Pr 1-120 Cl S(O)Me N Me Me 1-121 Cl S(O)Me N Me Et 1-122 Cl S(O)Me N Me c-Pr 1-123 Cl CF.sub.3 N Me Me 1-124 Cl CF.sub.3 N Me Et 1-125 Cl CF.sub.3 N Me c-Pr 1-126 Cl CF.sub.3 N Me CH.sub.2-c-Pr 1-127 Cl CF.sub.3 N Me CH.sub.2CF.sub.3 1-128 Cl CF.sub.3 N Me CH.sub.2CHF.sub.2 1-129 Cl CF.sub.3 N Me C(O)CH.sub.3 1-130 Cl CF.sub.3 N Me C(O)c-Pr 1-131 Cl CF.sub.3 N Me C(O)OMe 1-132 Cl CF.sub.3 N Me C(O)OEt 1-133 Cl CF.sub.3 N Me Ph 1-134 Cl CF.sub.3 N Me (2-Me)Ph 1-135 Cl CF.sub.3 N Et Et 1-136 Cl CF.sub.3 N Et c-Pr 1-137 Cl CF.sub.3 N Et CH.sub.2-c-Pr 1-138 Cl CF.sub.3 N Et CH.sub.2CF.sub.3 1-139 Cl CF.sub.3 N Et CH.sub.2CHF.sub.2 1-140 Cl CF.sub.3 N Et C(O)CH.sub.3 1-141 Cl CF.sub.3 N Et C(O)c-Pr 1-142 Cl CF.sub.3 N Et C(O)OMe 1-143 Cl CF.sub.3 N Et C(O)OEt 1-144 Cl CF.sub.3 N c-Pr c-Pr 1-145 Cl CF.sub.3 N c-Pr CH.sub.2-c-Pr 1-146 Cl CF.sub.3 N c-Pr CH.sub.2CF.sub.3 1-147 Cl CF.sub.3 N c-Pr CH.sub.2CHF.sub.2 1-148 Cl CF.sub.3 N c-Pr C(O)CH.sub.3 1-149 Cl CF.sub.3 N c-Pr C(O)c-Pr 1-150 Cl CF.sub.3 N c-Pr C(O)OMe 1-151 Cl CF.sub.3 N c-Pr C(O)OEt 1-152 Cl CF.sub.3 N —(CH.sub.2).sub.4— 1-153 Cl CF.sub.3 Pyrazol-1-yl 1-154 Cl CHF.sub.2 N Me Me 1-155 Cl CHF.sub.2 N Me Et 1-156 Cl CHF.sub.2 N Me c-Pr 1-157 Cl CHF.sub.2 N Me CH.sub.2-c-Pr 1-158 Cl CHF.sub.2 N Me CH.sub.2CF.sub.3 1-159 Cl CHF.sub.2 N Me CH.sub.2CHF.sub.2 1-160 Cl CHF.sub.2 N Me C(O)CH.sub.3 1-161 Cl CHF.sub.2 N Me C(O)c-Pr 1-162 Cl CHF.sub.2 N Me C(O)OMe 1-163 Cl CHF.sub.2 N Me C(O)OEt 1-164 Cl CHF.sub.2 N Me Ph 1-165 Cl CHF.sub.2 N Me (2-Me)Ph 1-166 Cl CHF.sub.2 N Et Et 1-167 Cl CHF.sub.2 N Et c-Pr 1-168 Cl CHF.sub.2 N Et CH.sub.2-c-Pr 1-169 Cl CHF.sub.2 N Et CH.sub.2CF.sub.3 1-170 Cl CHF.sub.2 N Et CH.sub.2CHF.sub.2 1-171 Cl CHF.sub.2 N Et C(O)CH.sub.3 1-172 Cl CHF.sub.2 N Et C(O)c-Pr 1-173 Cl CHF.sub.2 N Et C(O)OMe 1-174 Cl CHF.sub.2 N Et C(O)OEt 1-175 Cl CHF.sub.2 N c-Pr c-Pr 1-176 Cl CHF.sub.2 N c-Pr CH.sub.2-c-Pr 1-177 Cl CHF.sub.2 N c-Pr CH.sub.2CF.sub.3 1-178 Cl CHF.sub.2 N c-Pr CH.sub.2CHF.sub.2 1-179 Cl CHF.sub.2 N c-Pr C(O)CH.sub.3 1-180 Cl CHF.sub.2 N c-Pr C(O)c-Pr 1-181 Cl CHF.sub.2 N c-Pr C(O)OMe 1-182 Cl CHF.sub.2 N c-Pr C(O)OEt 1-183 Cl CHF.sub.2 N —(CH.sub.2).sub.4— 1-184 Cl CHF.sub.2 Pyrazol-1-yl 1-185 Cl C.sub.2F.sub.5 N Me Me 1-186 Cl C.sub.2F.sub.5 N Me Et 1-187 Cl C.sub.2F.sub.5 N Me c-Pr 1-188 Cl Cl N Me Me 1-189 Cl Cl N Me Et 1-190 Cl Cl N Me c-Pr 1-191 Cl Br N Me Me 1-192 Cl Br N Me Et 1-193 Cl Br N Me c-Pr 1-194 Cl Br N Me CH.sub.2-c-Pr 1-195 Cl Br N Me CH.sub.2CF.sub.3 1-196 Cl Br N Me CH.sub.2CHF.sub.2 1-197 Cl Br N Me C(O)CH.sub.3 1-198 Cl Br N Me C(O)c-Pr 1-199 Cl Br N Me C(O)OMe 1-200 Cl Br N Et Et 1-201 Cl Br N Et c-Pr 1-202 Cl Br N Et CH.sub.2-c-Pr 1-203 Cl Br N Et CH.sub.2CF.sub.3 1-204 Cl Br N Et CH.sub.2CHF.sub.2 1-205 Cl Br N Et C(O)CH.sub.3 1-206 Cl Br N Et C(O)c-Pr 1-207 Cl Br N Et C(O)OMe 1-208 Cl Br N c-Pr c-Pr 1-209 Cl Br N c-Pr CH.sub.2-c-Pr 1-210 Cl Br N c-Pr CH.sub.2CF.sub.3 1-211 Cl Br N c-Pr CH.sub.2CHF.sub.2 1-212 Cl Br N c-Pr C(O)CH.sub.3 1-213 Cl Br N c-Pr C(O)c-Pr 1-214 Cl Br N c-Pr C(O)OMe 1-215 Cl I N Me Me 1-216 Cl I N Me Et 1-217 Cl I N Me c-Pr 1-218 Br S(O)Me N Me Me 1-219 Br S(O)Me N Me Et 1-220 Br S(O)Me N Me c-Pr 1-221 Br CF.sub.3 N Me Me 1-222 Br CF.sub.3 N Me Et 1-223 Br CF.sub.3 N Me c-Pr 1-224 Br CF.sub.3 N Me CH.sub.2-c-Pr 1-225 Br CF.sub.3 N Me CH.sub.2CF.sub.3 1-226 Br CF.sub.3 N Me CH.sub.2CHF.sub.2 1-227 Br CF.sub.3 N Me C(O)CH.sub.3 1-228 Br CF.sub.3 N Me C(O)c-Pr 1-229 Br CF.sub.3 N Me C(O)OMe 1-230 Br CF.sub.3 N Et Et 1-231 Br CF.sub.3 N Et c-Pr 1-232 Br CF.sub.3 N Et CH.sub.2-c-Pr 1-233 Br CF.sub.3 N Et CH.sub.2CF.sub.3 1-234 Br CF.sub.3 N Et CH.sub.2CHF.sub.2 1-235 Br CF.sub.3 N Et C(O)CH.sub.3 1-236 Br CF.sub.3 N Et C(O)c-Pr 1-237 Br CF.sub.3 N Et C(O)OMe 1-238 Br CF.sub.3 N c-Pr c-Pr 1-239 Br CF.sub.3 N c-Pr CH.sub.2-c-Pr 1-240 Br CF.sub.3 N c-Pr CH.sub.2CF.sub.3 1-241 Br CF.sub.3 N c-Pr CH.sub.2CHF.sub.2 1-242 Br CF.sub.3 N c-Pr C(O)CH.sub.3 1-243 Br CF.sub.3 N c-Pr C(O)c-Pr 1-244 Br CF.sub.3 N c-Pr C(O)OMe 1-245 Br CHF.sub.2 N Me Me 1-246 Br CHF.sub.2 N Me Et 1-247 Br CHF.sub.2 N Me c-Pr 1-248 Br CHF.sub.2 N Me CH.sub.2-c-Pr 1-249 Br CHF.sub.2 N Me CH.sub.2CF.sub.3 1-250 Br CHF.sub.2 N Me CH.sub.2CHF.sub.2 1-251 Br CHF.sub.2 N Me C(O)CH.sub.3 1-252 Br CHF.sub.2 N Me C(O)c-Pr 1-253 Br CHF.sub.2 N Me C(O)OMe 1-254 Br CHF.sub.2 N Et Et 1-255 Br CHF.sub.2 N Et c-Pr 1-256 Br CHF.sub.2 N Et CH.sub.2-c-Pr 1-257 Br CHF.sub.2 N Et CH.sub.2CF.sub.3 1-258 Br CHF.sub.2 N Et CH.sub.2CHF.sub.2 1-259 Br CHF.sub.2 N Et C(O)CH.sub.3 1-260 Br CHF.sub.2 N Et C(O)c-Pr 1-261 Br CHF.sub.2 N Et C(O)OMe 1-262 Br CHF.sub.2 N c-Pr c-Pr 1-263 Br CHF.sub.2 N c-Pr CH.sub.2-c-Pr 1-264 Br CHF.sub.2 N c-Pr CH.sub.2CF.sub.3 1-265 Br CHF.sub.2 N c-Pr CH.sub.2CHF.sub.2 1-266 Br CHF.sub.2 N c-Pr C(O)CH.sub.3 1-267 Br CHF.sub.2 N c-Pr C(O)c-Pr 1-268 Br CHF.sub.2 N c-Pr C(O)OMe 1-269 Br C.sub.2F.sub.5 N Me Me 1-270 Br C.sub.2F.sub.5 N Me Et 1-271 Br C.sub.2F.sub.5 N Me c-Pr 1-272 1 S(O)Me N Me Me 1-273 I S(O)Me N Me Et 1-274 I S(O)Me N Me c-Pr 1-275 I CF.sub.3 N Me Me 1-276 I CF.sub.3 N Me Et 1-277 I CF.sub.3 N Me c-Pr 1-278 I CHF.sub.2 N Me Me 1-279 I CHF.sub.2 N Me Et 1-280 I CHF.sub.2 N Me c-Pr 1-281 CH.sub.2OMe CF.sub.3 N Me Me 1-282 CH.sub.2OMe CF.sub.3 N Me Et 1-283 CH.sub.2OMe CF.sub.3 N Me c-Pr 1-284 CH.sub.2OMe CHF.sub.2 N Me Me 1-285 CH.sub.2OMe CHF.sub.2 N Me Et 1-286 CH.sub.2OMe CHF.sub.2 N Me c-Pr 1-287 Et CF.sub.3 N Me Me 1-288 Et CF.sub.3 N Me Et 1-289 Et CF.sub.3 N Me c-Pr 1-290 Et CF.sub.3 N Me CH.sub.2-c-Pr 1-291 Et CF.sub.3 N Me CH.sub.2CF.sub.3 1-292 Et CF.sub.3 N Me CH.sub.2CHF.sub.2 1-293 Et CF.sub.3 N Me C(O)CH.sub.3 1-294 Et CF.sub.3 N Me C(O)c-Pr 1-295 Et CF.sub.3 N Me C(O)OMe 1-296 Et CF.sub.3 N Et Et 1-297 Et CF.sub.3 N Et c-Pr 1-298 Et CF.sub.3 N Et CH.sub.2-c-Pr 1-299 Et CF.sub.3 N Et CH.sub.2CF.sub.3 1-300 Et CF.sub.3 N Et ch.sub.2chf.sub.2 1-301 Et CF.sub.3 N Et C(O)CH.sub.3 1-302 Et CF.sub.3 N Et C(O)c-Pr 1-303 Et CF.sub.3 N Et C(O)OMe 1-304 Et CF.sub.3 N c-Pr c-Pr 1-305 Et CF.sub.3 N c-Pr CH.sub.2-c-Pr 1-306 Et CF.sub.3 N c-Pr CH.sub.2CF.sub.3 1-307 Et CF.sub.3 N c-Pr CH.sub.2CHF.sub.2 1-308 Et CF.sub.3 N c-Pr C(O)CH.sub.3 1-309 Et CF.sub.3 N c-Pr C(O)c-Pr 1-310 Et CF.sub.3 N c-Pr C(O)OMe 1-311 Et CHF.sub.2 N Me Me 1-312 Et CHF.sub.2 N Me Et 1-313 Et CHF.sub.2 N Me c-Pr 1-314 Et CHF.sub.2 N Me CH.sub.2-c-Pr 1-315 Et CHF.sub.2 N Me CH.sub.2CF.sub.3 1-316 Et CHF.sub.2 N Me CH.sub.2CHF.sub.2 1-317 Et CHF.sub.2 N Me C(O)CH.sub.3 1-318 Et CHF.sub.2 N Me C(O)c-Pr 1-319 Et CHF.sub.2 N Me C(O)OMe 1-320 Et CHF.sub.2 N Et Et 1-321 Et CHF.sub.2 N Et c-Pr 1-322 Et CHF.sub.2 N Et CH.sub.2-c-Pr 1-323 Et CHF.sub.2 N Et CH.sub.2CF.sub.3 1-324 Et CHF.sub.2 N Et CH.sub.2CHF.sub.2 1-325 Et CHF.sub.2 N Et C(O)CH.sub.3 1-326 Et CHF.sub.2 N Et C(O)c-Pr 1-327 Et CHF.sub.2 N Et C(O)OMe 1-328 Et CHF.sub.2 N c-Pr c-Pr 1-329 Et CHF.sub.2 N c-Pr CH.sub.2-c-Pr 1-330 Et CHF.sub.2 N c-Pr CH.sub.2CF.sub.3 1-331 Et CHF.sub.2 N c-Pr CH.sub.2CHF.sub.2 1-332 Et CHF.sub.2 N c-Pr C(O)CH.sub.3 1-333 Et CHF.sub.2 N c-Pr C(O)c-Pr 1-334 Et CHF.sub.2 N c-Pr C(O)OMe 1-335 Et C.sub.2F.sub.5 N Me Me 1-336 Et C.sub.2F.sub.5 N Me Et 1-337 Et C.sub.2F.sub.5 N Me c-Pr 1-338 c-Pr CF.sub.3 N Me Me 1-339 c-Pr CF.sub.3 N Me Et 1-340 c-Pr CF.sub.3 N Me c-Pr 1-341 c-Pr CF.sub.3 N Me CH.sub.2-c-Pr 1-342 c-Pr CF.sub.3 N Me CH.sub.2CF.sub.3 1-343 c-Pr CF.sub.3 N Me CH.sub.2CHF.sub.2 1-344 c-Pr CF.sub.3 N Me C(O)CH.sub.3 1-345 c-Pr CF.sub.3 N Me C(O)c-Pr 1-346 c-Pr CF.sub.3 N Me C(O)OMe 1-347 c-Pr CF.sub.3 N Et Et 1-348 c-Pr CF.sub.3 N Et c-Pr 1-349 c-Pr CF.sub.3 N Et CH.sub.2-c-Pr 1-350 c-Pr CF.sub.3 N Et CH.sub.2CF.sub.3 1-351 c-Pr CF.sub.3 N Et CH.sub.2CHF.sub.2 1-352 c-Pr CF.sub.3 N Et C(O)CH.sub.3 1-353 c-Pr CF.sub.3 N Et C(O)c-Pr 1-354 c-Pr CF.sub.3 N Et C(O)OMe 1-355 c-Pr CF.sub.3 N c-Pr c-Pr 1-356 c-Pr CF.sub.3 N c-Pr CH.sub.2-c-Pr 1-357 c-Pr CF.sub.3 N c-Pr CH.sub.2CF.sub.3 1-358 c-Pr CF.sub.3 N c-Pr CH.sub.2CHF.sub.2 1-359 c-Pr CF.sub.3 N c-Pr C(O)CH.sub.3 1-360 c-Pr CF.sub.3 N c-Pr C(O)c-Pr 1-361 c-Pr CF.sub.3 N c-Pr C(O)OMe 1-362 c-Pr CHF.sub.2 N Me Me 1-363 c-Pr CHF.sub.2 N Me Et 1-364 c-Pr CHF.sub.2 N Me c-Pr 1-365 c-Pr CHF.sub.2 N Me CH.sub.2-c-Pr 1-366 c-Pr CHF.sub.2 N Me CH.sub.2CF.sub.3 1-367 c-Pr CHF.sub.2 N Me CH.sub.2CHF.sub.2 1-368 c-Pr CHF.sub.2 N Me C(O)CH.sub.3 1-369 c-Pr CHF.sub.2 N Me C(O)c-Pr 1-370 c-Pr CHF.sub.2 N Me C(O)OMe 1-371 c-Pr CHF.sub.2 N Et Et 1-372 c-Pr CHF.sub.2 N Et c-Pr 1-373 c-Pr CHF.sub.2 N Et CH.sub.2-c-Pr 1-374 c-Pr CHF.sub.2 N Et CH.sub.2CF.sub.3 1-375 c-Pr CHF.sub.2 N Et CH.sub.2CHF.sub.2 1-376 c-Pr CHF.sub.2 N Et C(O)CH.sub.3 1-377 c-Pr CHF.sub.2 N Et C(O)c-Pr 1-378 c-Pr CHF.sub.2 N Et C(O)OMe 1-379 c-Pr CHF.sub.2 N c-Pr c-Pr 1-380 c-Pr CHF.sub.2 N c-Pr CH.sub.2-c-Pr 1-381 c-Pr CHF.sub.2 N c-Pr CH.sub.2CF.sub.3 1-382 c-Pr CHF.sub.2 N c-Pr CH.sub.2CHF.sub.2 1-383 c-Pr CHF.sub.2 N c-Pr C(O)CH.sub.3 1-384 c-Pr CHF.sub.2 N c-Pr C(O)c-Pr 1-385 c-Pr CHF.sub.2 N c-Pr C(O)OMe 1-386 c-Pr C.sub.2F.sub.5 N Me Me 1-387 c-Pr C.sub.2F.sub.5 N Me Et 1-388 c-Pr C.sub.2F.sub.5 N Me c-Pr 1-389 c-Pr SO(Me) N Me Me 1-390 c-Pr SO(Me) N Me Et 1-391 c-Pr SO.sub.2Me N Me c-Pr 1-392 CF.sub.3 CF.sub.3 N Me Me 1-393 CF.sub.3 CF.sub.3 N Me Et 1-394 CF.sub.3 CF.sub.3 N Me c-Pr 1-395 Me SO.sub.2Me N Me Me 1-396 Me SO.sub.2Me N Me Et 1-397 Me SO.sub.2Me N Me c-Pr 1-398 Cl Cl N Me Ph 1-399 Cl Cl N Me (2-Me)Ph 1-400 Cl CF.sub.3 [00019] embedded image 1-401 Me CF.sub.3 [00020] 1-402 Cl CHF.sub.2 [00021]

TABLE-US-00002 TABLE 2 Inventive compounds of the general formula (I) in whiCH Q is Q.sup.1 and R.sup.x is ethyl, and the other substituents have the definitions given below. [00022] embedded image No. X Y W Z.sup.1 Z.sup.2 2-1 Me F N Me Me 2-2 Me F N Me Et 2-3 Me F N Me c-Pr 2-4 Me Cl N Me Me 2-5 Me Cl N Me Et 2-6 Me Cl N Me c-Pr 2-7 Me Br N Me Me 2-8 Me Br N Me Et 2-9 Me Br N Me c-Pr 2-10 Me I N Me Me 2-11 Me I N Me Et 2-12 Me I N Me c-Pr 2-13 Me SMe N Me Me 2-14 Me SMe N Me Et 2-15 Me SMe N Me c-Pr 2-16 Me S(O)Me N Me Me 2-17 Me S(O)Me N Me Et 2-18 Me S(O)Me N Me c-Pr 2-19 Me CF.sub.3 N Me Me 2-20 Me CF.sub.3 N Me Et 2-21 Me CF.sub.3 N Me c-Pr 2-22 Me CF.sub.3 N Me CH.sub.2-c-Pr 2-23 Me CF.sub.3 N Me CH.sub.2CF.sub.3 2-24 Me CF.sub.3 N Me CH.sub.2CHF.sub.2 2-25 Me CF.sub.3 N Me C(O)CH.sub.3 2-26 Me CF.sub.3 N Me C(O)c-Pr 2-27 Me CF.sub.3 N Me C(O)OMe 2-28 Me CF.sub.3 N Me C(O)OEt 2-29 Me CF.sub.3 N Me Ph 2-30 Me CF.sub.3 N Me (2-Me)Ph 2-31 Me CF.sub.3 N Et Et 2-32 Me CF.sub.3 N Et c-Pr 2-33 Me CF.sub.3 N Et CH.sub.2-c-Pr 2-34 Me CF.sub.3 N Et CH.sub.2CF.sub.3 2-35 Me CF.sub.3 N Et CH.sub.2CHF.sub.2 2-36 Me CF.sub.3 N Et C(O)CH.sub.3 2-37 Me CF.sub.3 N Et C(O)c-Pr 2-38 Me CF.sub.3 N Et C(O)OMe 2-39 Me CF.sub.3 N Et C(O)OEt 2-40 Me CF.sub.3 N c-Pr c-Pr 2-41 Me CF.sub.3 N c-Pr CH.sub.2-c-Pr 2-42 Me CF.sub.3 N c-Pr CH.sub.2CF.sub.3 2-43 Me CF.sub.3 N c-Pr CH.sub.2CHF.sub.2 2-44 Me CF.sub.3 N c-Pr C(O)CH.sub.3 2-45 Me CF.sub.3 N c-Pr C(O)c-Pr 2-46 Me CF.sub.3 N c-Pr C(O)OMe 2-47 Me CF.sub.3 N c-Pr C(O)OEt 2-48 Me CF.sub.3 N —(CH.sub.2).sub.4— 2-49 Me CF.sub.3 Pyrazol-l-yl 2-50 Me CHF.sub.2 N Me Me 2-51 Me CHF.sub.2 N Me Et 2-52 Me CHF.sub.2 N Me c-Pr 2-53 Me CHF.sub.2 N Me CH.sub.2-c-Pr 2-54 Me CHF.sub.2 N Me CH.sub.2CF.sub.3 2-55 Me CHF.sub.2 N Me CH.sub.2CHF.sub.2 2-56 Me CHF.sub.2 N Me C(O)CH.sub.3 2-57 Me CHF.sub.2 N Me C(O)c-Pr 2-58 Me CHF.sub.2 N Me C(O)OMe 2-59 Me CHF.sub.2 N Et Et 2-60 Me CHF.sub.2 N Et c-Pr 2-71 Me CHF.sub.2 N Et CH.sub.2-c-Pr 2-72 Me CHF.sub.2 N Et CH.sub.2CF.sub.3 2-73 Me CHF.sub.2 N Et CH.sub.2CHF.sub.2 2-74 Me CHF.sub.2 N Et C(O)CH.sub.3 2-75 Me CHF.sub.2 N Et C(O)c-Pr 2-76 Me CHF.sub.2 N Et C(O)OMe 2-77 Me CHF.sub.2 N c-Pr c-Pr 2-78 Me CHF.sub.2 N c-Pr CH.sub.2-c-Pr 2-79 Me CHF.sub.2 N c-Pr CH.sub.2CF.sub.3 2-80 Me CHF.sub.2 N c-Pr CH.sub.2CHF.sub.2 2-81 Me CHF.sub.2 N c-Pr C(O)CH.sub.3 2-82 Me CHF.sub.2 N c-Pr C(O)c-Pr 2-83 Me CHF.sub.2 N c-Pr C(O)OMe 2-84 Me C.sub.2F.sub.5 N Me Me 2-85 Me C.sub.2F.sub.5 N Me Et 2-86 Me C.sub.2F.sub.5 N Me c-Pr 2-87 OMe Cl N Me Me 2-88 OMe Cl N Me Et 2-89 OMe Cl N Me c-Pr 2-90 OMe CF.sub.3 N Me Me 2-91 OMe CF.sub.3 N Me Et 2-92 OMe CF.sub.3 N Me c-Pr 2-93 OMe CHF.sub.2 N Me Me 2-94 OMe CHF.sub.2 N Me Et 2-95 OMe CHF.sub.2 N Me c-Pr 2-96 SMe SO.sub.2Me N Me Me 2-97 SMe SO.sub.2Me N Me Et 2-98 SMe SO.sub.2Me N Me c-Pr 2-99 SMe CF.sub.3 N Me Me 2-100 SMe CF.sub.3 N Me Et 2-101 SMe CF.sub.3 N Me c-Pr 2-102 SMe CHF.sub.2 N Me Me 2-103 SMe CHF.sub.2 N Me Et 2-104 SMe CHF.sub.2 N Me c-Pr 2-105 SEt CF.sub.3 N Me Me 2-106 SEt CF.sub.3 N Me Et 2-107 SEt CF.sub.3 N Me c-Pr 2-108 SEt CHF.sub.2 N Me Me 2-109 SEt CHF.sub.2 N Me Et 2-110 SEt CHF.sub.2 N Me c-Pr 2-111 F CF.sub.3 N Me Me 2-112 F CF.sub.3 N Me Et 2-113 F CF.sub.3 N Me c-Pr 2-114 F CHF.sub.2 N Me Me 2-115 F CHF.sub.2 N Me Et 2-116 F CHF.sub.2 N Me c-Pr 2-117 Cl SMe N Me Me 2-118 Cl SMe N Me Et 2-119 Cl SMe N Me c-Pr 2-120 Cl S(O)Me N Me Me 2-121 Cl S(O)Me N Me Et 2-122 Cl S(O)Me N Me c-Pr 2-123 Cl CF.sub.3 N Me Me 2-124 Cl CF.sub.3 N Me Et 2-125 Cl CF.sub.3 N Me c-Pr 2-126 Cl CF.sub.3 N Me CH.sub.2-c-Pr 2-127 Cl CF.sub.3 N Me CH.sub.2CF.sub.3 2-128 Cl CF.sub.3 N Me CH.sub.2CHF.sub.2 2-129 Cl CF.sub.3 N Me C(O)CH.sub.3 2-130 Cl CF.sub.3 N Me C(O)c-Pr 2-131 Cl CF.sub.3 N Me C(O)OMe 2-132 Cl CF.sub.3 N Me C(O)OEt 2-133 Cl CF.sub.3 N Me Ph 2-134 Cl CF.sub.3 N Me (2-Me)Ph 2-135 Cl CF.sub.3 N Et Et 2-136 Cl CF.sub.3 N Et c-Pr 2-137 Cl CF.sub.3 N Et CH.sub.2-c-Pr 2-138 Cl CF.sub.3 N Et CH.sub.2CF.sub.3 2-139 Cl CF.sub.3 N Et CH.sub.2CHF.sub.2 2-140 Cl CF.sub.3 N Et C(O)CH.sub.3 2-141 Cl CF.sub.3 N Et C(O)c-Pr 2-142 Cl CF.sub.3 N Et C(O)OMe 2-143 Cl CF.sub.3 N Et C(O)OEt 2-144 Cl CF.sub.3 N c-Pr c-Pr 2-145 Cl CF.sub.3 N c-Pr CH.sub.2-c-Pr 2-146 Cl CF.sub.3 N c-Pr CH.sub.2CF.sub.3 2-147 Cl CF.sub.3 N c-Pr CH.sub.2CHF.sub.2 2-148 Cl CF.sub.3 N c-Pr C(O)CH.sub.3 2-149 Cl CF.sub.3 N c-Pr C(O)c-Pr 2-150 Cl CF.sub.3 N c-Pr C(O)OMe 2-151 Cl CF.sub.3 N c-Pr C(O)OEt 2-152 Cl CF.sub.3 N —(CH.sub.3).sub.4— 2-153 Cl CF.sub.3 Pyrazol-l-yl 2-154 Cl CHF.sub.2 N Me Me 2-155 Cl CHF.sub.2 N Me Et 2-156 Cl CHF.sub.2 N Me c-Pr 2-157 Cl CHF.sub.2 N Me CH.sub.2-c-Pr 2-158 Cl CHF.sub.2 N Me CH.sub.2CF.sub.3 2-159 Cl CHF.sub.2 N Me CH.sub.2CHF.sub.2 2-160 Cl CHF.sub.2 N Me C(O)CH.sub.3 2-161 Cl CHF.sub.2 N Me C(O)c-Pr 2-162 Cl CHF.sub.2 N Me C(O)OMe 2-163 Cl CHF.sub.2 N Me C(O)OEt 2-164 Cl CHF.sub.2 N Me Ph 2-165 Cl CHF.sub.2 N Me (2-Me)Ph 2-166 Cl CHF.sub.2 N Et Et 2-167 Cl CHF.sub.2 N Et c-Pr 2-168 Cl CHF.sub.2 N Et CH.sub.2-c-Pr 2-169 Cl CHF.sub.2 N Et CH.sub.2CF.sub.3 2-170 Cl CHF.sub.2 N Et CH.sub.2CHF.sub.2 2-171 Cl CHF.sub.2 N Et C(O)CH.sub.3 2-172 Cl CHF.sub.2 N Et C(O)c-Pr 2-173 Cl CHF.sub.2 N Et C(O)OMe 2-174 Cl CHF.sub.2 N Et C(O)OEt 2-175 Cl CHF.sub.2 N c-Pr c-Pr 2-176 Cl CHF.sub.2 N c-Pr CH.sub.2-c-Pr 2-177 Cl CHF.sub.2 N c-Pr CH.sub.2CF.sub.3 2-178 Cl CHF.sub.2 N c-Pr CH.sub.2CHF.sub.2 2-179 Cl CHF.sub.2 N c-Pr C(O)CH.sub.3 2-180 Cl CHF.sub.2 N c-Pr C(O)c-Pr 2-181 Cl CHF.sub.2 N c-Pr C(O)OMe 2-182 Cl CHF.sub.2 N c-Pr C(O)OEt 2-183 Cl CHF.sub.2 N —(CH.sub.3).sub.4— 2-184 Cl CHF.sub.2 Pyrazol-l-yl 2-185 Cl C.sub.2F.sub.5 N Me Me 2-186 Cl C.sub.2F.sub.5 N Me Et 2-187 Cl C.sub.2F.sub.5 N Me c-Pr 2-188 Cl Cl N Me Me 2-189 Cl Cl N Me Et 2-190 Cl Cl N Me c-Pr 2-191 Cl Br N Me Me 2-192 Cl Br N Me Et 2-193 Cl Br N Me c-Pr 2-194 Cl Br N Me CH.sub.2-c-Pr 2-195 Cl Br N Me CH2CF3 2-196 Cl Br N Me CH2CHF2 2-197 Cl Br N Me C(O)CH.sub.3 2-198 Cl Br N Me C(O)c-Pr 2-199 Cl Br N Me C(O)OMe 2-200 Cl Br N Et Et 2-201 Cl Br N Et c-Pr 2-202 Cl Br N Et CH.sub.2-c-Pr 2-203 Cl Br N Et CH.sub.2CF.sub.3 2-204 Cl Br N Et CH.sub.2CHF.sub.2 2-205 Cl Br N Et C(O)CH.sub.3 2-206 Cl Br N Et C(O)c-Pr 2-207 Cl Br N Et C(O)OMe 2-208 Cl Br N c-Pr c-Pr 2-209 Cl Br N c-Pr CH.sub.2-c-Pr 2-210 Cl Br N c-Pr CH.sub.2CF.sub.3 2-211 Cl Br N c-Pr CH.sub.2CHF.sub.2 2-212 Cl Br N c-Pr C(O)CH.sub.3 2-213 Cl Br N c-Pr C(O)c-Pr 2-214 Cl Br N c-Pr C(O)OMe 2-215 Cl 1 N Me Me 2-216 Cl I N Me Et 2-217 Cl I N Me c-Pr 2-218 Br SO.sub.2Me N Me Me 2-219 Br SO.sub.2Me N Me Et 2-220 Br SO.sub.2Me N Me c-Pr 2-221 Br CF.sub.3 N Me Me 2-222 Br CF.sub.3 N Me Et 2-223 Br CF.sub.3 N Me c-Pr 2-224 Br CF.sub.3 N Me CH.sub.2-c-Pr 2-225 Br CF.sub.3 N Me CH.sub.2CF.sub.3 2-226 Br CF.sub.3 N Me CH.sub.2CHF.sub.2 2-227 Br CF.sub.3 N Me C(O)CH.sub.3 2-228 Br CF.sub.3 N Me C(O)c-Pr 2-229 Br CF.sub.3 N Me C(O)OMe 2-230 Br CF.sub.3 N Et Et 2-231 Br CF.sub.3 N Et c-Pr 2-232 Br CF.sub.3 N Et CH.sub.2-c-Pr 2-233 Br CF.sub.3 N Et CH.sub.2CF.sub.3 2-234 Br CF.sub.3 N Et CH.sub.2CHF.sub.2 2-235 Br CF.sub.3 N Et C(O)CH.sub.3 2-236 Br CF.sub.3 N Et C(O)c-Pr 2-237 Br CF.sub.3 N Et C(O)OMe 2-238 Br CF.sub.3 N c-Pr c-Pr 2-239 Br CF.sub.3 N c-Pr CH.sub.2-c-Pr 2-240 Br CF.sub.3 N c-Pr CH.sub.2CF.sub.3 2-241 Br CF.sub.3 N c-Pr CH.sub.2CHF.sub.2 2-242 Br CF.sub.3 N c-Pr C(O)CH.sub.3 2-243 Br CF.sub.3 N c-Pr C(O)c-Pr 2-244 Br CF.sub.3 N c-Pr C(O)OMe 2-245 Br CHF.sub.2 N Me Me 2-246 Br CHF.sub.2 N Me Et 2-247 Br CHF.sub.2 N Me c-Pr 2-248 Br CHF.sub.2 N Me CH.sub.2-c-Pr 2-249 Br CHF.sub.2 N Me CH.sub.2CF.sub.3 2-250 Br CHF.sub.2 N Me CH.sub.2CHF.sub.2 2-251 Br CHF.sub.2 N Me C(O)CH.sub.3 2-252 Br CHF.sub.2 N Me C(O)c-Pr 2-253 Br CHF.sub.2 N Me C(O)OMe 2-254 Br CHF.sub.2 N Et Et 2-255 Br CHF.sub.2 N Et c-Pr 2-256 Br CHF.sub.2 N Et CH.sub.2-c-Pr 2-257 Br CHF.sub.2 N Et CH.sub.2CF.sub.3 2-258 Br CHF.sub.2 N Et CH.sub.2CHF.sub.2 2-259 Br CHF.sub.2 N Et C(O)CH.sub.3 2-260 Br CHF.sub.2 N Et C(O)c-Pr 2-261 Br CHF.sub.2 N Et C(O)OMe 2-262 Br CHF.sub.2 N c-Pr c-Pr 2-263 Br CHF.sub.2 N c-Pr CH.sub.2-c-Pr 2-264 Br CHF.sub.2 N c-Pr CH.sub.2CF.sub.3 2-265 Br CHF.sub.2 N c-Pr CH.sub.2CHF.sub.2 2-266 Br CHF.sub.2 N c-Pr C(O)CH.sub.3 2-267 Br CHF.sub.2 N c-Pr C(O)c-Pr 2-268 Br CHF.sub.2 N c-Pr C(O)OMe 2-269 Br C.sub.2F.sub.5 N Me Me 2-270 Br C.sub.2F.sub.5 N Me Et 2-271 Br C.sub.2F.sub.5 N Me c-Pr 2-272 1 SO.sub.2Me N Me Me 2-273 I SO.sub.2Me N Me Et 2-274 I SO.sub.2Me N Me c-Pr 2-275 I CF.sub.3 N Me Me 2-276 I CF.sub.3 N Me Et 2-277 I CF.sub.3 N Me c-Pr 2-278 I CHF.sub.2 N Me Me 2-279 I CHF.sub.2 N Me Et 2-280 I CHF.sub.2 N Me c-Pr 2-281 CH.sub.2OMe CF.sub.3 N Me Me 2-282 CH.sub.2OMe CF.sub.3 N Me Et 2-283 CH.sub.2OMe CF.sub.3 N Me c-Pr 2-284 CH.sub.2OMe CHF.sub.2 N Me Me 2-285 CH.sub.2OMe CHF.sub.2 N Me Et 2-286 CH.sub.2OMe CHF.sub.2 N Me c-Pr 2-287 Et CF.sub.3 N Me Me 2-288 Et CF.sub.3 N Me Et 2-289 Et CF.sub.3 N Me c-Pr 2-290 Et CF.sub.3 N Me CH.sub.2-c-Pr 2-291 Et CF.sub.3 N Me CH.sub.2CF.sub.3 2-292 Et CF.sub.3 N Me CH.sub.2CHF.sub.2 2-293 Et CF.sub.3 N Me C(O)CH.sub.3 2-294 Et CF.sub.3 N Me C(O)c-Pr 2-295 Et CF.sub.3 N Me C(O)OMe 2-296 Et CF.sub.3 N Et Et 2-297 Et CF.sub.3 N Et c-Pr 2-298 Et CF.sub.3 N Et CH.sub.2-c-Pr 2-299 Et CF.sub.3 N Et CH.sub.2CF.sub.3 2-300 Et CF.sub.3 N Et CH.sub.2CHF.sub.2 2-301 Et CF.sub.3 N Et C(O)CH.sub.3 2-302 Et CF.sub.3 N Et C(O)c-Pr 2-303 Et CF.sub.3 N Et C(O)OMe 2-304 Et CF.sub.3 N c-Pr c-Pr 2-305 Et CF.sub.3 N c-Pr CH.sub.2-c-Pr 2-306 Et CF.sub.3 N c-Pr CH.sub.2CF.sub.3 2-307 Et CF.sub.3 N c-Pr CH.sub.2CHF.sub.2 2-308 Et CF.sub.3 N c-Pr C(O)CH.sub.3 2-309 Et CF.sub.3 N c-Pr C(O)c-Pr 2-310 Et CF.sub.3 N c-Pr C(O)OMe 2-311 Et CHF.sub.2 N Me Me 2-312 Et CHF.sub.2 N Me Et 2-313 Et CHF.sub.2 N Me c-Pr 2-314 Et CHF.sub.2 N Me CH.sub.2-c-Pr 2-315 Et CHF.sub.2 N Me CH.sub.2CF.sub.3 2-316 Et CHF.sub.2 N Me CH.sub.2CHF.sub.2 2-317 Et CHF.sub.2 N Me C(O)CH.sub.3 2-318 Et CHF.sub.2 N Me C(O)c-Pr 2-319 Et CHF.sub.2 N Me C(O)OMe 2-320 Et CHF.sub.2 N Et Et 2-321 Et CHF.sub.2 N Et c-Pr 2-322 Et CHF.sub.2 N Et CH.sub.2-c-Pr 2-323 Et CHF.sub.2 N Et CH.sub.2CF.sub.3 2-324 Et CHF.sub.2 N Et CH.sub.2CHF.sub.2 2-325 Et CHF.sub.2 N Et C(O)CH.sub.3 2-326 Et CHF.sub.2 N Et C(O)c-Pr 2-327 Et CHF.sub.2 N Et C(O)OMe 2-328 Et CHF.sub.2 N c-Pr c-Pr 2-329 Et CHF.sub.2 N c-Pr CH.sub.2-c-Pr 2-330 Et CHF.sub.2 N c-Pr CH.sub.2CF.sub.3 2-331 Et CHF.sub.2 N c-Pr CH.sub.2CHF.sub.2 2-332 Et CHF.sub.2 N c-Pr C(O)CH.sub.3 2-333 Et CHF.sub.2 N c-Pr C(O)c-Pr 2-334 Et CHF.sub.2 N c-Pr C(O)OMe 2-335 Et C.sub.2F.sub.5 N Me Me 2-336 Et C.sub.2F.sub.5 N Me Et 2-337 Et C.sub.2F.sub.5 N Me c-Pr 2-338 c-Pr CF.sub.3 N Me Me 2-339 c-Pr CF.sub.3 N Me Et 2-340 c-Pr CF.sub.3 N Me c-Pr 2-341 c-Pr CF.sub.3 N Me CH.sub.2-c-Pr 2-342 c-Pr CF.sub.3 N Me CH.sub.2CF.sub.3 2-343 c-Pr CF.sub.3 N Me CH.sub.2CHF.sub.2 2-344 c-Pr CF.sub.3 N Me C(O)CH.sub.3 2-345 c-Pr CF.sub.3 N Me C(O)c-Pr 2-346 c-Pr CF.sub.3 N Me C(O)OMe 2-347 c-Pr CF.sub.3 N Et Et 2-348 c-Pr CF.sub.3 N Et c-Pr 2-349 c-Pr CF.sub.3 N Et CH.sub.2-c-Pr 2-350 c-Pr CF.sub.3 N Et CH.sub.2CF.sub.3 2-351 c-Pr CF.sub.3 N Et CH.sub.2CHF.sub.2 2-352 c-Pr CF.sub.3 N Et C(O)CH.sub.3 2-353 c-Pr CF.sub.3 N Et C(O)c-Pr 2-354 c-Pr CF.sub.3 N Et C(O)OMe 2-355 c-Pr CF.sub.3 N c-Pr c-Pr 2-356 c-Pr CF.sub.3 N c-Pr CH.sub.2-c-Pr 2-357 c-Pr CF.sub.3 N c-Pr CH.sub.2CF.sub.3 2-358 c-Pr CF.sub.3 N c-Pr CH.sub.2CHF.sub.2 2-359 c-Pr CF.sub.3 N c-Pr C(O)CH.sub.3 2-360 c-Pr CF.sub.3 N c-Pr C(O)c-Pr 2-361 c-Pr CF.sub.3 N c-Pr C(O)OMe 2-362 c-Pr CHF.sub.2 N Me Me 2-363 c-Pr CHF.sub.2 N Me Et 2-364 c-Pr CHF.sub.2 N Me c-Pr 2-365 c-Pr CHF.sub.2 N Me CH.sub.2-c-Pr 2-366 c-Pr CHF.sub.2 N Me CH.sub.2CF.sub.3 2-367 c-Pr CHF.sub.2 N Me CH.sub.2CHF.sub.2 2-368 c-Pr CHF.sub.2 N Me C(O)CH.sub.3 2-369 c-Pr CHF.sub.2 N Me C(O)c-Pr 2-370 c-Pr CHF.sub.2 N Me C(O)OMe 2-371 c-Pr CHF.sub.2 N Et Et 2-372 c-Pr CHF.sub.2 N Et c-Pr 2-373 c-Pr CHF.sub.2 N Et CH.sub.2-c-Pr 2-374 c-Pr CHF.sub.2 N Et CH.sub.2CF.sub.3 2-375 c-Pr CHF.sub.2 N Et CH.sub.2CHF.sub.2 2-376 c-Pr CHF.sub.2 N Et C(O)CH.sub.3 2-377 c-Pr CHF.sub.2 N Et C(O)c-Pr 2-378 c-Pr CHF.sub.2 N Et C(O)OMe 2-379 c-Pr CHF.sub.2 N c-Pr c-Pr 2-380 c-Pr CHF.sub.2 N c-Pr CH.sub.2-c-Pr 2-381 c-Pr CHF.sub.2 N c-Pr CH.sub.2CF.sub.3 2-382 c-Pr CHF.sub.2 N c-Pr CH.sub.2CHF.sub.2 2-383 c-Pr CHF.sub.2 N c-Pr C(O)CH.sub.3 2-384 c-Pr CHF.sub.2 N c-Pr C(O)c-Pr 2-385 c-Pr CHF.sub.2 N c-Pr C(O)OMe 2-386 c-Pr C.sub.2F.sub.5 N Me Me 2-387 c-Pr C.sub.2F.sub.5 N Me Et 2-388 c-Pr C.sub.2F.sub.5 N Me c-Pr 2-389 c-Pr SO.sub.2Me N Me Me 2-390 c-Pr SO.sub.2Me N Me Et 2-391 c-Pr SO.sub.2Me N Me c-Pr 2-392 CF.sub.3 CF.sub.3 N Me Me 2-393 CF.sub.3 CF.sub.3 N Me Et 2-394 CF.sub.3 CF.sub.3 N Me c-Pr 2-395 Me SO.sub.2Me N Me Me 2-396 Me SO.sub.2Me N Me Et 2-397 Me SO.sub.2Me N Me c-Pr 2-398 Cl CF.sub.3 [00023] embedded image 2-399 Me CF.sub.3 [00024] 2-340 Cl CHF.sub.2 [00025]

TABLE-US-00003 TABLE 3 Inventive compounds of the general formula (1) in which Q is Q.sup.1 and R.sup.x is propyl, and the other substituents have the definitions given below. [00026] embedded image No. X Y W Z.sup.1 Z.sup.2 3-1 Me F N Me Me 3-2 Me F N Me Et 3-3 Me F N Me c-Pr 3-4 Me Cl N Me Me 3-5 Me Cl N Me Et 3-6 Me Cl N Me c-Pr 3-7 Me Br N Me Me 3-8 Me Br N Me Et 3-9 Me Br N Me c-Pr 3-10 Me I N Me Me 3-11 Me I N Me Et 3-12 Me I N Me c-Pr 3-13 Me SMe N Me Me 3-14 Me SMe N Me Et 3-15 Me SMe N Me c-Pr 3-16 Me S(O)Me N Me Me 3-17 Me S(O)Me N Me Et 3-18 Me S(O)Me N Me c-Pr 3-19 Me CF.sub.3 N Me Me 3-20 Me CF.sub.3 N Me Et 3-21 Me CF.sub.3 N Me c-Pr 3-22 Me CF.sub.3 N Me CH.sub.2-c-Pr 3-23 Me CF.sub.3 N Me CH.sub.2CF.sub.3 3-24 Me CF.sub.3 N Me CH.sub.2CHF.sub.2 3-25 Me CF.sub.3 N Me C(O)CH.sub.3 3-26 Me CF.sub.3 N Me C(O)c-Pr 3-27 Me CF.sub.3 N Me C(O)OMe 3-28 Me CF.sub.3 N Me C(O)OEt 3-29 Me CF.sub.3 N Me Ph 3-30 Me CF.sub.3 N Me (2-Me)Ph 3-31 Me CF.sub.3 N Et Et 3-32 Me CF.sub.3 N Et c-Pr 3-33 Me CF.sub.3 N Et CH.sub.2-c-Pr 3-34 Me CF.sub.3 N Et CH.sub.2CF.sub.3 3-35 Me CF.sub.3 N Et CH.sub.2CHF.sub.2 3-36 Me CF.sub.3 N Et C(O)CH.sub.3 3-37 Me CF.sub.3 N Et C(O)c-Pr 3-38 Me CF.sub.3 N Et C(O)OMe 3-39 Me CF.sub.3 N Et C(O)OEt 3-40 Me CF.sub.3 N c-Pr c-Pr 3-41 Me CF.sub.3 N c-Pr CH.sub.2-c-Pr 3-42 Me CF.sub.3 N c-Pr CH.sub.2CF.sub.3 3-43 Me CF.sub.3 N c-Pr CH.sub.2CHF.sub.2 3-44 Me CF.sub.3 N c-Pr C(O)CH.sub.3 3-45 Me CF.sub.3 N c-Pr C(O)c-Pr 3-46 Me CF.sub.3 N c-Pr C(O)OMe 3-47 Me CF.sub.3 N c-Pr C(O)OEt 3-48 Me CF.sub.3 N —(CH.sub.2).sub.4— 3-49 Me CF.sub.3 Pyrazol-l-yl 3-50 Me CHF.sub.2 N Me Me 3-51 Me CHF.sub.2 N Me Et 3-52 Me CHF.sub.2 N Me c-Pr 3-53 Me CHF.sub.2 N Me CH.sub.2-c-Pr 3-54 Me CHF.sub.2 N Me CH.sub.2CF.sub.3 3-55 Me CHF.sub.2 N Me CH.sub.2CHF.sub.2 3-56 Me CHF.sub.2 N Me C(O)CH.sub.3 3-57 Me CHF.sub.2 N Me C(O)c-Pr 3-58 Me CHF.sub.2 N Me C(O)OMe 3-59 Me CHF.sub.2 N Et Et 3-60 Me CHF.sub.2 N Et c-Pr 3-71 Me CHF.sub.2 N Et CH.sub.2-c-Pr 3-72 Me CHF.sub.2 N Et CH.sub.2CF.sub.3 3-73 Me CHF.sub.2 N Et CH.sub.2CHF.sub.2 3-74 Me CHF.sub.2 N Et C(O)CH.sub.3 3-75 Me CHF.sub.2 N Et C(O)c-Pr 3-76 Me CHF.sub.2 N Et C(O)OMe 3-77 Me CHF.sub.2 N c-Pr c-Pr 3-78 Me CHF.sub.2 N c-Pr CH.sub.2-c-Pr 3-79 Me CHF.sub.2 N c-Pr CH.sub.2CF.sub.3 3-80 Me CHF.sub.2 N c-Pr CH.sub.2CHF.sub.2 3-81 Me CHF.sub.2 N c-Pr C(O)CH.sub.3 3-82 Me CHF.sub.2 N c-Pr C(O)c-Pr 3-83 Me CHF.sub.2 N c-Pr C(O)OMe 3-84 Me C.sub.2F.sub.5 N Me Me 3-85 Me C.sub.2F.sub.5 N Me Et 3-86 Me C.sub.2F.sub.5 N Me c-Pr 3-87 OMe Cl N Me Me 3-88 OMe Cl N Me Et 3-89 OMe Cl N Me c-Pr 3-90 OMe CF.sub.3 N Me Me 3-91 OMe CF.sub.3 N Me Et 3-92 OMe CF.sub.3 N Me c-Pr 3-93 OMe CHF.sub.2 N Me Me 3-94 OMe CHF.sub.2 N Me Et 3-95 OMe CHF.sub.2 N Me c-Pr 3-96 SMe SO.sub.2Me N Me Me 3-97 SMe SO.sub.2Me N Me Et 3-98 SMe SO.sub.2Me N Me c-Pr 3-99 SMe CF.sub.3 N Me Me 3-100 SMe CF.sub.3 N Me Et 3-101 SMe CF.sub.3 N Me c-Pr 3-102 SMe CHF.sub.2 N Me Me 3-103 SMe CHF.sub.2 N Me Et 3-104 SMe CHF.sub.2 N Me c-Pr 3-105 SEt CF.sub.3 N Me Me 3-106 SEt CF.sub.3 N Me Et 3-107 SEt CF.sub.3 N Me c-Pr 3-108 SEt CHF.sub.2 N Me Me 3-109 SEt CHF.sub.2 N Me Et 3-110 SEt CHF.sub.2 N Me c-Pr 3-111 F CF.sub.3 N Me Me 3-112 F CF.sub.3 N Me Et 3-113 F CF.sub.3 N Me c-Pr 3-114 F CHF.sub.2 N Me Me 3-115 F CHF.sub.2 N Me Et 3-116 F CHF.sub.2 N Me c-Pr 3-117 Cl SMe N Me Me 3-118 Cl SMe N Me Et 3-119 Cl SMe N Me c-Pr 3-120 Cl S(O)Me N Me Me 3-121 Cl S(O)Me N Me Et 3-122 Cl S(O)Me N Me c-Pr 3-123 Cl CF.sub.3 N Me Me 3-124 Cl CF.sub.3 N Me Et 3-125 Cl CF.sub.3 N Me c-Pr 3-126 Cl CF.sub.3 N Me CH.sub.2-c-Pr 3-127 Cl CF.sub.3 N Me CH.sub.2CF.sub.3 3-128 Cl CF.sub.3 N Me CH.sub.2CHF.sub.2 3-129 Cl CF.sub.3 N Me C(O)CH.sub.3 3-130 Cl CF.sub.3 N Me C(O)c-Pr 3-131 Cl CF.sub.3 N Me C(O)OMe 3-132 Cl CF.sub.3 N Me C(O)OEt 3-133 Cl CF.sub.3 N Me Ph 3-134 Cl CF.sub.3 N Me (2-Me)Ph 3-135 Cl CF.sub.3 N Et Et 3-136 Cl CF, N Et c-Pr 3-137 Cl CF.sub.3 N Et CH.sub.2-c-Pr 3-138 Cl CF.sub.3 N Et CH.sub.2CF.sub.3 3-139 Cl CF.sub.3 N Et CH.sub.2CHF.sub.2 3-140 Cl CF.sub.3 N Et C(O)CH.sub.3 3-141 Cl CF.sub.3 N Et C(O)c-Pr 3-142 Cl CF.sub.3 N Et C(O)OMe 3-143 Cl CF.sub.3 N Et C(O)OEt 3-144 Cl CF.sub.3 N c-Pr c-Pr 3-145 Cl CF.sub.3 N c-Pr CH.sub.2-c-Pr 3-146 Cl CF.sub.3 N c-Pr CH.sub.2CF.sub.3 3-147 Cl CF.sub.3 N c-Pr CH.sub.2CHF.sub.2 3-148 Cl CF.sub.3 N c-Pr C(O)CH.sub.3 3-149 Cl CF.sub.3 N c-Pr C(O)c-Pr 3-150 Cl CF.sub.3 N c-Pr C(O)OMe 3-151 Cl CF.sub.3 N c-Pr C(O)OEt 3-152 Cl CF.sub.3 N —(CH.sub.2).sub.4— 3-153 Cl CF.sub.3 Pyrazol-l-yl 3-154 Cl CHF.sub.2 N Me Me 3-155 Cl CHF.sub.2 N Me Et 3-156 Cl CHF.sub.2 N Me c-Pr 3-157 Cl CHF.sub.2 N Me CH.sub.2-c-Pr 3-158 Cl CHF.sub.2 N Me CH.sub.2CF.sub.3 3-159 Cl CHF.sub.2 N Me CH.sub.2CHF.sub.2 3-160 Cl CHF.sub.2 N Me C(O)CH.sub.3 3-161 Cl CHF.sub.2 N Me C(O)c-Pr 3-162 Cl CHF.sub.2 N Me C(O)OMe 3-163 Cl CHF.sub.2 N Me C(O)OEt 3-164 Cl CHF.sub.2 N Me Ph 3-165 Cl CHF.sub.2 N Me (2-Me)Ph 3-166 Cl CHF.sub.2 N Et Et 3-167 Cl CHF.sub.2 N Et c-Pr 3-168 Cl CHF.sub.2 N Et CH.sub.2-c-Pr 3-169 Cl CHF.sub.2 N Et CH.sub.2CF.sub.3 3-170 Cl CHF.sub.2 N Et CH.sub.2CHF.sub.2 3-171 Cl CHF.sub.2 N Et C(O)CH.sub.3 3-172 Cl CHF.sub.2 N Et C(O)c-Pr 3-173 Cl CHF.sub.2 N Et C(O)OMe 3-174 Cl CHF.sub.2 N Et C(O)OEt 3-175 Cl CHF.sub.2 N c-Pr c-Pr 3-176 Cl CHF.sub.2 N c-Pr CH.sub.2-c-Pr 3-177 Cl CHF.sub.2 N c-Pr CH.sub.2CF.sub.3 3-178 Cl CHF.sub.2 N c-Pr CH.sub.2CHF.sub.2 3-179 Cl CHF.sub.2 N c-Pr C(O)CH.sub.3 3-180 Cl CHF.sub.2 N c-Pr C(O)c-Pr 3-181 Cl CHF.sub.2 N c-Pr C(O)OMe 3-182 Cl CHF.sub.2 N c-Pr C(O)OEt 3-183 Cl CHF.sub.2 N —(CH.sub.2).sub.4— 3-184 Cl CHF.sub.2 Pyrazol-l-yl 3-185 Cl C.sub.2F.sub.5 N Me Me 3-186 Cl C.sub.2F.sub.5 N Me Et 3-187 Cl C.sub.2F.sub.5 N Me c-Pr 3-188 Cl Cl N Me Me 3-189 Cl Cl N Me Et 3-190 Cl Cl N Me c-Pr 3-191 Cl Br N Me Me 3-192 Cl Br N Me Et 3-193 Cl Br N Me c-Pr 3-194 Cl Br N Me CH.sub.2-c-Pr 3-195 Cl Br N Me CH.sub.2CF.sub.3 3-196 Cl Br N Me CH.sub.2CHF.sub.2 3-197 Cl Br N Me C(O)CH.sub.3 3-198 Cl Br N Me C(O)c-Pr 3-199 Cl Br N Me C(O)OMe 3-200 Cl Br N Et Et 3-201 Cl Br N Et c-Pr 3-202 Cl Br N Et CH.sub.2-c-Pr 3-203 Cl Br N Et CH.sub.2CF.sub.3 3-204 Cl Br N Et CH.sub.2CHF.sub.2 3-205 Cl Br N Et C(O)CH.sub.3 3-206 Cl Br N Et C(O)c-Pr 3-207 Cl Br N Et C(O)OMe 3-208 Cl Br N c-Pr c-Pr 3-209 Cl Br N c-Pr CH.sub.2-c-Pr 3-210 Cl Br N c-Pr CH.sub.2CF.sub.3 3-211 Cl Br N c-Pr CH.sub.2CHF.sub.2 3-212 Cl Br N c-Pr C(O)CH.sub.3 3-213 Cl Br N c-Pr C(O)c-Pr 3-214 Cl Br N c-Pr C(O)OMe 3-215 Cl I N Me Me 3-216 Cl I N Me Et 3-217 Cl I N Me c-Pr 3-218 Br SO.sub.2Me N Me Me 3-219 Br SO.sub.2Me N Me Et 3-220 Br SO.sub.2Me N Me c-Pr 3-221 Br CF.sub.3 N Me Me 3-222 Br CF.sub.3 N Me Et 3-223 Br CF.sub.3 N Me c-Pr 3-224 Br CF.sub.3 N Me CH.sub.2-c-Pr 3-225 Br CF.sub.3 N Me CH.sub.2CF.sub.3 3-226 Br CF.sub.3 N Me CH.sub.2CHF.sub.2 3-227 Br CF.sub.3 N Me C(O)CH.sub.3 3-228 Br CF.sub.3 N Me C(O)c-Pr 3-229 Br CF.sub.3 N Me C(O)OMe 3-230 Br CF.sub.3 N Et Et 3-231 Br CF.sub.3 N Et c-Pr 3-232 Br CF.sub.3 N Et CH.sub.2-c-Pr 3-233 Br CF.sub.3 N Et CH.sub.2CF.sub.3 3-234 Br CF.sub.3 N Et CH.sub.2CHF.sub.2 3-235 Br CF.sub.3 N Et C(O)CH.sub.3 3-236 Br CF.sub.3 N Et C(O)c-Pr 3-237 Br CF.sub.3 N Et C(O)OMe 3-238 Br CF.sub.3 N c-Pr c-Pr 3-239 Br CF.sub.3 N c-Pr CH.sub.2-c-Pr 3-240 Br CF.sub.3 N c-Pr CH.sub.2CF.sub.3 3-241 Br CF.sub.3 N c-Pr CH.sub.2CHF.sub.2 3-242 Br CF.sub.3 N c-Pr C(O)CH.sub.3 3-243 Br CF.sub.3 N c-Pr C(O)c-Pr 3-244 Br CF, N c-Pr C(O)OMe 3-245 Br CHF.sub.2 N Me Me 3-246 Br CHF.sub.2 N Me Et 3-247 Br CHF.sub.2 N Me c-Pr 3-248 Br CHF.sub.2 N Me CH.sub.2-c-Pr 3-249 Br CHF.sub.2 N Me CH.sub.2CF.sub.3 3-250 Br CHF.sub.2 N Me CH.sub.2CHF.sub.2 3-251 Br CHF.sub.2 N Me C(O)CH.sub.3 3-252 Br CHF.sub.2 N Me C(O)c-Pr 3-253 Br CHF.sub.2 N Me C(O)OMe 3-254 Br CHF.sub.2 N Et Et 3-255 Br CHF.sub.2 N Et c-Pr 3-256 Br CHF.sub.2 N Et CH.sub.2-c-Pr 3-257 Br CHF.sub.2 N Et CH.sub.2CF.sub.3 3-258 Br CHF.sub.2 N Et CH.sub.2CHF.sub.2 3-259 Br CHF.sub.2 N Et C(O)CH.sub.3 3-260 Br CHF.sub.2 N Et C(O)c-Pr 3-261 Br CHF.sub.2 N Et C(O)OMe 3-262 Br CHF.sub.2 N c-Pr c-Pr 3-263 Br CHF.sub.2 N c-Pr CH.sub.2-c-Pr 3-264 Br CHF.sub.2 N c-Pr CH.sub.2CF.sub.3 3-265 Br CHF.sub.2 N c-Pr CH.sub.2CHF.sub.2 3-266 Br CHF.sub.2 N c-Pr C(O)CH.sub.3 3-267 Br CHF.sub.2 N c-Pr C(O)c-Pr 3-268 Br CHF.sub.2 N c-Pr C(O)OMe 3-269 Br CaFs N Me Me 3-270 Br C.sub.2F.sub.5 N Me Et 3-271 Br C.sub.2F.sub.5 N Me c-Pr 3-272 1 SO.sub.2Me N Me Me 3-273 I SO.sub.2Me N Me Et 3-274 I SO.sub.2Me N Me c-Pr 3-275 I CF.sub.3 N Me Me 3-276 I CF.sub.3 N Me Et 3-277 I CF.sub.3 N Me c-Pr 3-278 I CHF.sub.2 N Me Me 3-279 I CHF.sub.2 N Me Et 3-280 I CHF.sub.2 N Me c-Pr 3-281 CH.sub.2OMe CF.sub.3 N Me Me 3-282 CH.sub.2OMe CF.sub.3 N Me Et 3-283 CH.sub.2OMe CF.sub.3 N Me c-Pr 3-284 CH.sub.2OMe CHF.sub.2 N Me Me 3-285 CH.sub.2OMe CHF.sub.2 N Me Et 3-286 CH.sub.2OMe CHF.sub.2 N Me c-Pr 3-287 Et CF.sub.3 N Me Me 3-288 Et CF.sub.3 N Me Et 3-289 Et CF.sub.3 N Me c-Pr 3-290 Et CF.sub.3 N Me CH.sub.2-c-Pr 3-291 Et CF.sub.3 N Me CH.sub.2CF.sub.3 3-292 Et CF.sub.3 N Me CH.sub.2CHF.sub.2 3-293 Et CF.sub.3 N Me C(O)CH.sub.3 3-294 Et CF.sub.3 N Me C(O)c-Pr 3-295 Et CF.sub.3 N Me C(O)OMe 3-296 Et CF.sub.3 N Et Et 3-297 Et CF.sub.3 N Et c-Pr 3-298 Et CF.sub.3 N Et CH.sub.2-c-Pr 3-299 Et CF.sub.3 N Et CH.sub.2CF.sub.3 3-300 Et CF.sub.3 N Et CH.sub.2CHF.sub.2 3-301 Et CF.sub.3 N Et C(O)CH.sub.3 3-302 Et CF.sub.3 N Et C(O)c-Pr 3-303 Et CF.sub.3 N Et C(O)OMe 3-304 Et CF.sub.3 N c-Pr c-Pr 3-305 Et CF.sub.3 N c-Pr CH.sub.2-c-Pr 3-306 Et CF.sub.3 N c-Pr CH.sub.2CF.sub.3 3-307 Et CF.sub.3 N c-Pr CH.sub.2CHF.sub.2 3-308 Et CF.sub.3 N c-Pr C(O)CH.sub.3 3-309 Et CF.sub.3 N c-Pr C(O)c-Pr 3-310 Et CF.sub.3 N c-Pr C(O)OMe 3-311 Et CHF.sub.2 N Me Me 3-312 Et CHF.sub.2 N Me Et 3-313 Et CHF.sub.2 N Me c-Pr 3-314 Et CHF.sub.2 N Me CH.sub.2-c-Pr 3-315 Et CHF.sub.2 N Me CH.sub.2CF.sub.3 3-316 Et CHF.sub.2 N Me CH.sub.2CHF.sub.2 3-317 Et CHF.sub.2 N Me C(O)CH.sub.3 3-318 Et CHF.sub.2 N Me C(O)c-Pr 3-319 Et CHF.sub.2 N Me C(O)OMe 3-320 Et CHF.sub.2 N Et Et 3-321 Et CHF.sub.2 N Et c-Pr 3-322 Et CHF.sub.2 N Et CH.sub.2-c-Pr 3-323 Et CHF.sub.2 N Et CH.sub.2CF.sub.3 3-324 Et CHF.sub.2 N Et CH.sub.2CHF.sub.2 3-325 Et CHF.sub.2 N Et C(O)CH.sub.3 3-326 Et CHF.sub.2 N Et C(O)c-Pr 3-327 Et CHF.sub.2 N Et C(O)OMe 3-328 Et CHF.sub.2 N c-Pr c-Pr 3-329 Et CHF.sub.2 N c-Pr CH.sub.2-c-Pr 3-330 Et CHF.sub.2 N c-Pr CH.sub.2CF.sub.3 3-331 Et CHF.sub.2 N c-Pr CH.sub.2CHF.sub.2 3-332 Et CHF.sub.2 N c-Pr C(O)CH.sub.3 3-333 Et CHF.sub.2 N c-Pr C(O)c-Pr 3-334 Et CHF.sub.2 N c-Pr C(O)OMe 3-335 Et C.sub.2F.sub.5 N Me Me 3-336 Et C.sub.2F.sub.5 N Me Et 3-337 Et C.sub.2F.sub.5 N Me c-Pr 3-338 c-Pr CF.sub.3 N Me Me 3-339 c-Pr CF.sub.3 N Me Et 3-340 c-Pr CF.sub.3 N Me c-Pr 3-341 c-Pr CF.sub.3 N Me CH.sub.2-c-Pr 3-342 c-Pr CF.sub.3 N Me CH.sub.2CF.sub.3 3-343 c-Pr CF.sub.3 N Me CH.sub.2CHF.sub.2 3-344 c-Pr CF.sub.3 N Me C(O)CH.sub.3 3-345 c-Pr CF.sub.3 N Me C(O)c-Pr 3-346 c-Pr CF.sub.3 N Me C(O)OMe 3-347 c-Pr CF.sub.3 N Et Et 3-348 c-Pr CF.sub.3 N Et c-Pr 3-349 c-Pr CF.sub.3 N Et CH.sub.2-c-Pr 3-350 c-Pr CF.sub.3 N Et CH.sub.2CF.sub.3 3-351 c-Pr CF.sub.3 N Et CH.sub.2CHF.sub.2 3-352 c-Pr CF, N Et C(O)CH.sub.3 3-353 c-Pr CF.sub.3 N Et C(O)c-Pr 3-354 c-Pr CF.sub.3 N Et C(O)OMe 3-355 c-Pr CF.sub.3 N c-Pr c-Pr 3-356 c-Pr CF.sub.3 N c-Pr CH.sub.2-c-Pr 3-357 c-Pr CF.sub.3 N c-Pr CH.sub.2CF.sub.3 3-358 c-Pr CF.sub.3 N c-Pr CH.sub.2CHF.sub.2 3-359 c-Pr CF.sub.3 N c-Pr C(O)CH.sub.3 3-360 c-Pr CF.sub.3 N c-Pr C(O)c-Pr 3-361 c-Pr CF.sub.3 N c-Pr C(O)OMe 3-362 c-Pr CHF.sub.2 N Me Me 3-363 c-Pr CHF.sub.2 N Me Et 3-364 c-Pr CHF.sub.2 N Me c-Pr 3-365 c-Pr CHF.sub.2 N Me CH.sub.2-c-Pr 3-366 c-Pr CHF.sub.2 N Me CH.sub.2CF.sub.3 3-367 c-Pr CHF.sub.2 N Me CH.sub.2CHF.sub.2 3-368 c-Pr CHF.sub.2 N Me C(O)CH.sub.3 3-369 c-Pr CHF.sub.2 N Me C(O)c-Pr 3-370 c-Pr CHF.sub.2 N Me C(O)OMe 3-371 c-Pr CHF.sub.2 N Et Et 3-372 c-Pr CHF.sub.2 N Et c-Pr 3-373 c-Pr CHF.sub.2 N Et CH.sub.2-c-Pr 3-374 c-Pr CHF.sub.2 N Et CH.sub.2CF.sub.3 3-375 c-Pr CHF.sub.2 N Et CH.sub.2CHF.sub.2 3-376 c-Pr CHF.sub.2 N Et C(O)CH.sub.3 3-377 c-Pr CHF.sub.2 N Et C(O)c-Pr 3-378 c-Pr CHF.sub.2 N Et C(O)OMe 3-379 c-Pr CHF.sub.2 N c-Pr c-Pr 3-380 c-Pr CHF.sub.2 N c-Pr CH.sub.2-c-Pr 3-381 c-Pr CHF.sub.2 N c-Pr CH.sub.2CF.sub.3 3-382 c-Pr CHF.sub.2 N c-Pr CH.sub.2CHF.sub.2 3-383 c-Pr CHF.sub.2 N c-Pr C(O)CH.sub.3 3-384 c-Pr CHF.sub.2 N c-Pr C(O)c-Pr 3-385 c-Pr CHF.sub.2 N c-Pr C(O)OMe 3-386 c-Pr C.sub.2F.sub.5 N Me Me 3-387 c-Pr C.sub.2F.sub.5 N Me Et 3-388 c-Pr C.sub.2F.sub.5 N Me c-Pr 3-389 c-Pr SO.sub.2Me N Me Me 3-390 c-Pr SO.sub.2Me N Me Et 3-391 c-Pr SO.sub.2Me N Me c-Pr 3-392 CF.sub.3 CF.sub.3 N Me Me 3-393 CF.sub.3 CF.sub.3 N Me Et 3-394 CF.sub.3 CF.sub.3 N Me c-Pr 3-395 Me SO.sub.2Me N Me Me 3-396 Me SO.sub.2Me N Me Et 3-397 Me SO.sub.2Me N Me c-Pr

[0405] NMR data for numerous inventive compounds of the formula (I) mentioned in tables above are disclosed below for further characterization:

[0406] Ex. no. 1-19: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.80 (br s); 7.85 (d, 1H); 7.81 (d, 1H); 4.01 (s, 3H); 3.04 (s, 3H); 2.74 (s, 3H); 2.29 (s, 3H);

[0407] Ex. no. 1-20: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.82 (br s, 1H); 7.85 (d, 1H); 7.82 (d, 1H); 4.01 (s, 3H); 3.60 (m, 1H); 3.45 (m, 1H); 3.05 (m, 2H); 3.00 (s, 3H); 2.71 (s, 3H); 2.30 (s, 3H); 1.14 (t, 3H); 1.02 (t, 3H);

[0408] Ex. no. 1-21: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.79 (br s, 1H); 7.84 (d, 1H); 7.80 (d, 1H); 4.01 (s, 3H); 2.98 (s, 3H); 2.88 (m, 1H); 2.31 (s, 3H); 0.81 (m, 2H); 0.47 (m, 2H);

[0409] Ex. no. 1-24: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.81 (br s, 1H); 7.89 (d, 1H); 7.85 (d, 1H); 6.30 (tt, 1H); 4.02 (s, 3H); 3.98 (m, 2H); 2.84 (s, 3H); 2.33 (s, 3H);

[0410] Ex. no. 1-31: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.80 (br s, 1H); 7.85 (d, 1H); 7.81 (d, 1H); 4.01 (s, 3H); 3.56 (m, 1H); 3.45 (m, 1H); 3.06 (m, 2H); 2.32 (s, 3H); 1.16 (t, 3H); 1.01 (t, 3H);

[0411] Ex. no. 1-32: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.79 (br s, 1H); 7.84 (d, 1H); 7.80 (d, 1H); 4.01 (s, 3H); 3.55 (m, 1H); 3.45 (m, 1H); 2.51 (m, 1H); 2.32 (s, 3H); 1.16 (t, 3H); 0.48 (m, 4H);

[0412] Ex. no. 1-40: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.78 (br s, 1H); 7.84 (d, 1H); 7.79 (d, 1H); 4.01 (s, 3H); 2.67 (m, 1H); 2.36 (m, 1H); 2.29 (s, 3H); 0.86 (m, 2H); 0.81 (m, 2H); 0.60 (m, 2H); 0.46 (m, 2H);

[0413] Ex. no. 1-50: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.72 (br s, 1H); 7.80 (d, 1H); 7.66 (d, 1H); 6.89 (t, 1H); 4.00 (s, 3H); 3.05 (s, 3H); 2.74 (s, 3H); 2.28 (s, 3H);

[0414] Ex. no. 1-51: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.72 (br s, 1H); 7.79 (d, 1H); 7.67 (d, 1H); 6.89 (t, 11); 4.00 (s, 3H); 3.54 (m, 2H); 3.02 (s, 3H); 2.29 (s, 3H); 1.16 (t, 3H);

[0415] Ex. no. 1-59: .sup.1H-NMR (400 MHz, DMSO-4): δ=11.73 (br s, 1H); 7.80 (d, 1H); 7.68 (d, 1H); 6.86 (t, 1H); 4.01 (s, 3H); 3.59 (m, 1H); 3.47 (m, 1H); 3.07 (m, 2H); 2.31 (s, 3H); 1.19 (t, 3H); 0.99 (t, 3H);

[0416] Ex. no. 1-123: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=12.01 (br s, 1H); 8.00 (s, 2H); 4.02 (s, 3H); 3.04 (s, 3H); 2.78 (s, 3H);

[0417] Ex. no. 1-124: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=12.01 (br s, 1H); 8.00 (s, 2H); 4.02 (s, 3H); 3.58 (m, 1H); 3.48 (m, 1H); 3.10 (m, 2H); 3.01 (s, 3H); 2.76 (s, 3H); 1.14 (t, 3H); 1.07 (t, 3H);

[0418] Ex. no. 1-125: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=12.03 (br s, 1H); 8.00 (d, 2H); 4.01 (s, 3H); 3.00 (s, 3H); 2.60 (m, 1H); 0.82 (m, 1H); 0.72 (m, 1H); 0.50 (m, 2H);

[0419] Ex. no. 1-126: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=12.02 (br s, 1H); 8.00 (s, 2H); 4.02 (br s, 3H); 3.43 (m, 2H); 3.36 (m, 2H); 3.11 (s, 3H); 2.94 (2, 2H); 2.83 (s, 3H); 1.09 (m, 1H); 0.86 (m, 1H); 0.51 (m, 4H); 0.32 (m, 2H); 0.13 (m, 2H);

[0420] Ex. no. 1-128: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=12.038 (br s, 1H); 8.04 (br s, 2H); 6.27 (tt, 1H); 4.02 (s, 3H); 4.00 (m, 2H); 2.89 (s, 3H);

[0421] Ex. no. 1-135: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=12.03 (br s, 1H); 8.00 (br s, 2H); 4.02 (t, 3H); 3.55 (m, 1H); 3.46 (m, 1H); 3.10 (m, 2H); 1.16 (t, 3H); 1.05 (t, 3H);

[0422] Ex. no. 1-136: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=12.06 (br s, 1H); 8.00 (br s, 2H); 4.02 (s, 3H); 3.64 (br s, 1H); 3.53 (m, 2H); 1.17 (t, 3H); 0.71 (m, 1H); 0.51 (m, 3H);

[0423] Ex. no. 1-144: .sup.1H-NMR (400 MHz, DMSO-4): δ=12.03 (br s, 1H); 7.99 (br s, 2H); 4.01 (s, 3H); 2.68 (m, 1H); 0.83 (m, 5H); 0.52 (m, 3H);

[0424] Ex. no. 1-152: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=12.01 (br s, 1H); 8.00 (s, 2H); 4.02 (s, 3H); 3.51 (m, 2H); 3.12 (m, 1H); 3.02 (m, 1H); 1.88 (m, 4H);

[0425] Ex. no. 1-153: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=12.11 (br s, 1H); 8.75 (br s, 1H); 8.20 (d, 1H); 8.14 (d, 1H); 7.97 (s, 1H); 6.81 (br s, 1H); 4.01 (s, 3H);

[0426] Ex. no. 1-154: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.98 (br s, 1H); 7.93 (d, 1H); 7.82 (d, 1H); 6.98 (t, 1H); 4.01 (s, 3H); 3.05 (s, 3H); 2.78 (s, 3H);

[0427] Ex. no. 1-155: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.97 (br s, 1H); 7.93 (br d, 1H); 7.82 (d, 1H); 6.98 (t, 1H); 4.02 (s, 3H); 3.54 (m, 1H); 3.02 (m, 1H); 2.76 (s, 3H); 1.16 (t, 3H);

[0428] Ex. no. 1-156: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.99 (br s, 1H); 7.93 (d, 1H); 7.81 (d, 1H); 6.96 (t, 1H); 4.02 (s, 3H); 3.02 (s, 3H); 2.65 (m, 1H); 0.79 (m, 1H); 0.52 (m, 1H); 0.44 (m, 2H);

[0429] Ex. no. 1-159: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.99 (br s, 1H); 7.99 (d, 1H); 7.87 (d, 1H); 7.01 (t, 1H); 6.31 (tt, 1H); 4.02 (s, 3H); 3.98 (m, 2H); 2.88 (s, 3H);

[0430] Ex. no. 1-166: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.97 (br s, 1H); 7.94 (d, 1H); 7.82 (d, 1H); 4.02 (s, 3H); 3.59 (m, 1H); 3.48 (m, 1H); 3.10 (m, 2H); 1.18 (t, 3H); 1.04 (t, 3H);

[0431] Ex. no. 1-167: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.99 (br s, 1H); 7.92 (d, 1H); 7.82 (d, 1H); 6.94 (t, 1H); 4.01 (s, 3H); 3.73 (m, 1H); 3.32 (m, 1H); 2.68 (m, 1H); 1.20 (t, 3H); 0.69 (m, 1H); 0.57 (m, 1H); 0.42 (m, 2H);

[0432] Ex. no. 1-175: .sup.1H-NMR (400 MHz, DMSO-4): δ=11.98 (br s, 1H); 7.92 (br s, 1H); 7.82 (d, 1H); 6.99 (t, 1H); 4.01 (s, 3H); 2.72 (m, 1H); 2.50 (m, 1H); 0.84 (m, 5H); 0.59 (m, 1H); 0.49 (m, 1H); 0.40 (m, 1H);

[0433] Ex. no. 1-191: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.91 (br s, 1H); 7.87 (d, 1H); 7.72 (d, 1H); 4.00 (s, 3H); 3.05 (s, 3H); 2.82 (s, 3H);

[0434] Ex. no. 1-192: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.91 (br s, 1H); 7.87 (d, 1H); 7.71 (d, 1H); 4.00 (s, 3H); 3.54 (m 2H); 3.02 (s, 3H); 1.17 (t, 3H);

[0435] Ex. no. 1-200: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.91 (br s, 1H); 7.86 (d, 1H); 7.71 (d, 1H); 4.35 (q, 2H); 3.99 (s, 3H); 3.51 (m, 2H); 3.13 (m, 2H); 1.19 (t, 3H); 1.09 (t, 3H);

[0436] Ex. no. 1-395: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.82 (br s, 1H); 7.95 (d, 1H); 7.89 (d, 1H); 4.01 (s, 3H); 3.25 (s, 3H); 3.01 (s, 3H); 2.72 (s, 3H); 2.31 (s, 3H);

[0437] Ex. no. 1-398: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.83 (s, 1H); 7.89 (d, 1H); 7.81 (d, 1H); 7.37-7.22 (m, 4H); 4.02 (s, 3H); 3.19 (s, 3H);

[0438] Ex. no. 1-399: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.96 (s, 1H); 7.86 (d, 1H); 7.82 (d, 1H); 7.38-7.25 (m, 3H); 4.00 (s, 3H); 3.09 (s, 3H); 2.34 (s, 3H);

[0439] Ex. no. 1-400: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=12.04 (br s, 1H); 8.03 (m, 2H); 4.48 (m, 1H); 4.15 (q, 2H); 4.02 (t, 3H); 3.21 (m, 1H); 2.31 (m, 1H); 1.95 (m, 4H); 1.21 (t, 3H);

[0440] Ex. no. 1-401: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.80 (br s, 1H); 7.87 (d, 1H); 7.83 (d, 1H); 4.56 (m, 1H); 4.16 (q, 2H); 4.02 (s, 3H); 3.21 (m, 1H); 3.08 (m, 1H); 2.48 (s, 3H); 2.31 (m, 1H); 1.90 (m, 2H); 1.23 (t, 3H);

[0441] Ex. no. 1-402: .sup.1H-NMR (400 MHz, DMSO-4): δ=11.98 (br s, 1H); 8.01 (d, 1H); 7.72 (d, 1H); 7.00 (t, 1H); 4.60 (m, 1H); 4.21 (m, 2H); 4.02 (s, 3H); 3.28 (m, 1H); 3.29 (m, 1H); 2.38 (m, 1H); 1.98 (m, 1H); 1.91 (m, 2H); 1.25 (t, 3H);

[0442] Ex. no. 2-19: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.69 (br s, 1H); 7.84 (d, 1H); 7.81 (d, 1H); 4.36 (q, 2H); 3.04 (s, 3H); 2.74 (s, 3H); 2.29 (s, 3H); 1.48 (t, 3H);

[0443] Ex. no. 2-21: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.68 (br s, 1H); 7.82 (d, 1H); 7.80 (d, 1H); 4.36 (q, 2H); 2.98 (s, 3H); 2.88 (m, 1H); 2.30 (s, 3H); 1.48 (t, 3H); 0.82 (m, 1H); 0.73 (m, 1H); 0.52 (m, 1H); 0.46 (m, 1H);

[0444] Ex. no. 2-31: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.70 (br s, 1H); 7.84 (d, 1H); 7.81 (d, 1H); 4.36 (q, 2H); 3.57 (m, 1H); 3.46 (m, 1H); 3.07 (m, 2H); 2.31 (s, 3H); 1.48 (t, 3H); 1.16 (t, 3H); 1.01 (t, 3H);

[0445] Ex. no. 2-32: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.68 (br s, 1H); 7.83 (d, 1H); 7.80 (d, 1H); 4.36 (q, 2H); 3.55 (m, 1H); 3.45 (m, 1H); 2.51 (m, 1H); 2.32 (s, 3H); 1.48 (t, 3H); 1.16 (t, 3H); 0.51 (m, 4H);

[0446] Ex. no. 2-50: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.62 (br s, 1); 7.89 (d, 1H); 7.66 (d, 1H); 6.89 (t, 1H); 4.35 (q, 2H); 3.05 (s, 3H); 2.74 (s, 3H); 2.28 (s, 3H); 1.48 (t, 3H);

[0447] Ex. no. 2-51: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.62 (br s, 1H); 7.79 (d, 1H); 7.67 (d, 1H); 6.89 (t, 11); 4.35 (q, 2H); 3.53 (m, 2H); 3.03 (s, 3H); 2.29 (s, 3H); 1.48 (t, 3H); 1.17 (t, 3H);

[0448] Ex. no. 2-59: .sup.1H-NMR (400 MHz, DMSO-4): δ=11.63 (br s, 1H); 7.79 (d, 1H); 7.68 (d, 1H); 6.86 (t, 1H); 4.35 (q, 2H); 3.60 (m, 1H); 3.46 (m, 1H); 3.07 (m, 2H); 2.30 (s, 3H); 1.48 (t, 3H); 1.19 (t, 3H); 0.99 (s, 3H);

[0449] Ex. no. 2-123: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.92 (br s, 1H); 8.00 (s, 2H); 4.38 (q, 2H); 3.04 (s, 3H); 2.79 (s, 3H); 1.48 (t, 3H);

[0450] Ex. no. 2-124: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.92 (br s, 1H); 7.99 (s, 2H); 4.38 (q, 2H); 3.58 (m, 1H); 3.47 (m, 1H); 3.10 (m, 2H); 3.00 (s, 3H); 2.76 (s, 3H); 1.48 (t, 3H); 1.14 (t, 3H); 1.07 (t, 3H);

[0451] Ex. no. 2-125: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.94 (br s, 1H); 7.99 (d, 2H); 4.37 (q, 2H); 3.00 (s, 3H); 2.59 (m, 1H); 1.47 (t, 3H); 0.81 (m, 1H); 0.70 (m, 1H); 0.49 (m, 2H);

[0452] Ex. no. 2-126: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.92 (br s, 1H); 8.00 (s, 2H); 4.38 (q, 2H); 3.44 (m, 1H); 3.35 (m, 1H); 3.11 (s, 3H); 2.94 (m, 2H); 2.83 (s, 3H); 1.48 (t, 3H); 1.08 (m, 1H); 0.86 (m, 1H); 0.50 (m, 4H); 0.32 (m, 2H); 0.13 (m, 2H);

[0453] Ex. no. 2-128: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.95 (br s, 1H); 8.04 (br s, 2H); 6.27 (tt, 1H); 4.38 (q, 2H); 3.98 (m, 2H); 2.89 (s, 3H); 1.48 (t, 3H);

[0454] Ex. no. 2-135: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.93 (br s, 1H); 7.99 (br s, 2H); 4.37 (q, 2H); 3.55 (m, 1H); 3.47 (m, 1H); 3.09 (m, 2H); 1.47 (t, 3H); 1.16 (t, 3H); 1.05 (t, 3H);

[0455] Ex. no. 2-136: .sup.1H-NMR (400 MHz, DMSO-4): δ=11.94 (br s, 1H); 7.99 (br s, 2H); 4.37 (q, 2H); 3.05 (m, 1H); 3.48 (m, 1H); 3.00 (m, 1H); 1.49 (t, 3H); 1.18 (t, 3H); 0.70 (m, 2H); 0.51 (m, 2H);

[0456] Ex. no. 2-144: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.93 (br s, 1H); 7.99 (br s, 2H); 4.37 (q, 2H); 2.68 (m, 2H); 1.47 (t, 3H); 0.85 (m, 5H); 0.52 (m, 3H);

[0457] Ex. no. 2-152: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.92 (br s, 1H); 8.00 (s, 2H); 4.38 (q, 2H); 3.51 (m, 2H); 3.12 (m, 1H); 3.04 (m, 1H); 1.88 (m, 4H); 1.48 (t, 3H);

[0458] Ex. no. 2-153: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=12.00 (br s, 1H); 8.75 (br s, 1H); 8.19 (d, 1H); 8.14 (d, 1H); 7.97 (s, 1H); 6.81 (br s, 1H); 4.36 (q, 2H); 1.47 (t, 3H);

[0459] Ex. no. 2-154: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.89 (br s, 1H); 7.93 (d, 1H); 7.82 (d, 1H); 6.98 (t, 1H); 4.37 (q, 2H); 3.05 (s, 3H); 2.78 (s, 3H); 1.48 (t, 3H);

[0460] Ex. no. 2-155: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.87 (br s, 1H); 7.91 (br s, 1H); 7.82 (d, 1H); 6.98 (t, 1H); 4.37 (q, 2H); 3.53 (m, 1H); 3.02 (m, 1H); 2.76 (s, 3H); 1.47 (t, 3H); 1.16 (t, 3H);

[0461] Ex. no. 2-156: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.87 (br s, 1H); 7.92 (d, 1H); 7.80 (d, 1H); 6.96 (t, 1H); 4.37 (q, 2H); 3.02 (s, 3H); 2.67 (m, 1H); 1.48 (t, 3H); 0.80 (m, 1H); 0.52 (m, 1H); 0.43 (m, 2H);

[0462] Ex. no. 2-159: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.89 (br s, 1H); 7.97 (d, 1H); 7.85 (d, 1H); 7.01 (t, 1H); 6.31 (tt, 1H); 4.38 (q, 2H); 3.98 (m, 2H); 2.88 (s, 3H); 1.48 (t, 3H);

[0463] Ex. no. 2-166: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.88 (br s, 1H); 7.93 (d, 1H); 7.82 (d, 1H); 6.95 (t, 1H); 4.37 (q, 2H); 3.58 (m, 1H); 3.48 (m, 1H); 3.10 (m, 2H); 1.48 (t, 3H); 1.18 (t, 3H); 1.04 (t, 3H);

[0464] Ex. no. 2-167: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.87 (br s, 1H); 7.92 (br s, 1H); 7.82 (d, 1H); 6.94 (t, 1H); 4.37 (q, 2H); 3.74 (m, 1H); 3.33 (m, 1H); 2.67 (m, 1H); 1.48 (t, 3H); 1.20 (t, 3H); 0.69 (m, 1H); 0.57 (m, 1H); 0.41 (m, 2H);

[0465] Ex. no. 2-175: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.86 (br s, 1H); 7.90 (br s, 1H); 7.82 (d, 1H); 6.99 (t, 1H); 4.37 (q, 2H); 2.72 (m, 1H); 2.50 (m, 1H); 1.47 (t, 3H); 0.85 (m, 5H); 0.59 (m, 1H); 0.50 (m, 1H); 0.40 (m, 1H);

[0466] Ex. no. 2-191: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.81 (br s, 1H); 7.87 (d, 1H); 7.71 (d, 1H); 4.35 (q, 2H); 3.05 (s, 3H); 2.82 (s, 3H); 1.47 (t, 3H);

[0467] Ex. no. 2-192: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.81 (br s, 1H); 7.87 (d, 1H); 7.70 (d, 1H); 4.36 (q, 2H); 3.54 (m, 2H); 3.02 (s, 3H); 1.47 (t, 3H); 1.17 (t, 3H);

[0468] Ex. no. 2-200: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.82 (br s, 1H); 7.86 (d, 1H); 7.70 (d, 1H); 4.35 (q, 2H); 3.52 (m, 2H); 3.13 (m, 2H); 1.46 (t, 3H); 1.19 (t, 3H); 1.09 (t, 3H);

[0469] Ex. no. 2-340: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.89 (br s, 1H); 8.00 (d, 1H); 7.92 (d, 1H); 7.00 (t, 1H); 4.60 (m, 1H); 4.38 (q, 2H); 4.20 (m, 2H); 3.28 (m, 1H); 3.19 (m, 1H); 2.37 (m, 1H); 1.99 (m, 1H); 1.92 (m, 2H); 1.49 (t, 3H); 1.25 (t, 3H);

[0470] Ex. no. 2-398: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.94 (br s, 1H); 8.02 (br s, 1H); 4.47 (m, 1H); 4.38 (m, 2H); 4.15 (m, 2H); 3.21 (m, 1H); 3.31 (m, 1H); 1.96 (m, 4H); 1.49 (t, 3H); 1.22 (t, 3H);

[0471] Ex. no. 3-123: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.90 (br s, 1H); 7.99 (s, 2H); 4.32 (t, 2H); 3.04 (s, 3H); 2.79 (s, 3H); 1.89 (m, 2H); 0.88 (t, 3H);

[0472] Ex. no. 3-124: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.90 (br s, 1H); 7.99 (s, 2H); 4.32 (t, 2H); 3.59 (m, 1H); 3.46 (m, 1H); 3.10 (m 2H); 3.00 (s, 3H); 2.76 (s, 3H); 1.89 (m, 2H); 1.14 (t, 3H); 1.06 (t, 3H); 0.88 (t, 3H);

[0473] Ex. no. 3-126: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.91 (br s, 1H); 7.99 (s, 2H); 4.33 (t, 2H); 3.45 (m, 1H); 3.35 (m, 1H); 3.11 (s, 3H); 2.94 (m, 2H); 2.83 (s, 3H); 1.89 (m, 2H); 1.08 (m, 1H); 0.88 (t, 3H); 0.85 (m, 1H); 0.51 (m, 4H); 0.32 (m, 2H); 0.13 (m, 2H);

[0474] Ex. no. 3-152: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.91 (br s, 1H); 7.99 (s, 2H); 4.32 (t, 2H); 3.50 (m, 2H); 3.12 (m, 1H); 3.04 (m, 1H); 1.89 (m, 6H); 0.88 (t, 3H);

[0475] Ex. no. 3-153: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ=11.98 (br s, 1H); 8.75 (s, 1H); 8.18 (d, 1H); 8.14 (d, 1H); 7.97 (s, 1H); 6.81 (s, 1H); 4.31 (t, 2H); 1.88 (m, 2H); 0.88 (t, 3H).

B. Formulation Examples

[0476] 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. [0477] 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. [0478] 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. [0479] d) An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I) and/or salts thereof, 75 parts by weight of cyclohexanone as a solvent and 10 parts by weight of ethoxylated nonylphenol as an emulsifier. [0480] e) Water-dispersible granules are obtained by mixing [0481] 75 parts by weight of a compound of the formula (I) and/or salts thereof, [0482] 10 parts by weight of calcium lignosulfonate, [0483] 5 parts by weight of sodium lauryl sulfate, [0484] 3 parts by weight of polyvinyl alcohol and [0485] 7 parts by weight of kaolin, [0486] 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. [0487] f) Water-dispersible granules are also obtained by homogenizing and precomminuting, in a colloid mill, [0488] 25 parts by weight of a compound of the formula (I) and/or salts thereof, [0489] 5 parts by weight of sodium 2,2′-dinaphthylmethane-6,6′-disulfonate [0490] 2 parts by weight of sodium oleoylmethyltaurate, [0491] 1 part by weight of polyvinyl alcohol, [0492] 17 parts by weight of calcium carbonate and [0493] 50 parts by weight of water, [0494] 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.

C. Biological Examples

[0495] The abbreviations used for the harmful plants mean:

TABLE-US-00004 ABUTH Abutilon theophrasti ALOMY Alopecurus myosuroides AVEFA Avena fatua AMARE Amaranthus retroflexus CYPES Cyperus esculentus DIGSA Digitaria sanguinalis ECHCG Echinochloa HORMU Hordeum murinum crus-galli LOLMU Lolium multiflorum LOLRI Lolium rigidum MATIN Matricaria inodora PHBPU Pharbitis purpurea POLCO Polygonum SETVI Setaria viridis convolvulus STEME Stellaria media VERPE Veronica persica VIOTR Viola tricolor

[0496] 1. Pre-Emergence Herbicidal Action Against Harmful Plants

[0497] 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 equivalent 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 illustrative manner, the post-emergence herbicidal action of the compounds of the invention, the herbicidal activity being stated in percent.

TABLE-US-00005 TABLE 1 Example number Dosage [g/ha] ABUTH a: Pre-emergence action at 20 g/ha against ABUTH in % 1-398 20 100 1-123 20 80 2-123 20 100 1-126 20 100 2-126 20 100 3-126 20 100 2-124 20 100 3-124 20 100 1-152 20 100 2-152 20 100 3-152 20 100 2-153 20 100 3-153 20 100 1-153 20 100 1-19 20 90 2-19 20 80 2-154 20 100 1-144 20 80 2-144 20 90 1-128 20 100 2-136 20 100 2-398 20 80 1-125 20 100 2-125 20 90 1-135 20 100 2-135 20 90 1-136 20 90 1-401 20 100 2-31 20 100 2-32 20 100 2-399 20 100 1-24 20 100 1-155 20 100 2-155 20 100 1-166 20 100 2-166 20 100 1-156 20 100 2-156 20 100 1-159 20 100 2-159 20 100 1-167 20 100 2-167 20 100 1-175 20 90 2-175 20 100 2-51 20 100 2-59 20 100 1-191 20 100 2-191 20 90 1-192 20 80 2-192 20 100 1-200 20 90 2-200 20 100 b: Pre-emergence action at 80 g/ha against ABUTH in % 1-395 80 90 1-398 80 100 1-399 80 100 1-123 80 100 2-123 80 100 3-123 80 100 1-126 80 100 2-126 80 100 3-126 80 100 2-124 80 100 3-124 80 100 1-152 80 100 2-152 80 100 3-152 80 100 2-153 80 100 3-153 80 100 1-153 80 100 1-19 80 100 2-19 80 100 1-20 80 100 1-154 80 100 2-154 80 100 1-400 80 100 1-144 80 100 2-144 80 100 1-128 80 100 2-136 80 100 2-398 80 100 1-125 80 100 2-125 80 100 1-135 80 100 2-135 80 100 1-136 80 100 2-128 80 100 1-401 80 100 2-31 80 100 1-21 80 100 1-32 80 100 2-32 80 100 2-399 80 100 1-31 80 100 2-21 80 100 1-24 80 100 1-40 80 80 1-155 80 100 2-155 80 100 1-166 80 100 2-166 80 100 1-156 80 100 2-156 80 100 1-159 80 100 2-159 80 100 1-167 80 100 2-167 80 100 1-175 80 100 2-175 80 100 2-50 80 100 2-51 80 100 1-59 80 100 2-59 80 100 1-50 80 100 1-51 80 100 1-191 80 100 2-191 80 100 1-192 80 100 2-192 80 100 1-200 80 100 2-200 80 100 c: Pre-emergence action at 3200 g/ha against ABUTH in % 1-395 320 100 1-398 320 100 1-399 320 100 1-123 320 100 2-123 320 100 3-123 320 100 1-126 320 100 2-126 320 100 3-126 320 100 1-124 320 90 2-124 320 100 3-124 320 100 1-152 320 100 2-152 320 100 3-152 320 100 2-153 320 100 3-153 320 100 1-153 320 100

TABLE-US-00006 TABLE 2 Example number Dosage [g/ha] ALOMY a: Pre-emergence action at 20 g/ha against ALOMY in % 1-398 20 80 1-124 20 80 1-152 20 80 1-154 20 90 2-154 20 80 2-136 20 90 2-156 20 90 1-159 20 90 2-175 20 80 1-191 20 90 2-191 20 90 2-200 20 90 b: Pre-emergence action at 80 g/ha against ALOMY in % 1-398 80 100 1-399 80 80 1-123 80 80 2-123 80 90 3-123 80 80 1-126 80 80 2-126 80 80 1-124 80 90 2-124 80 80 3-124 80 80 1-152 80 90 2-152 80 90 1-153 80 80 1-19 80 80 2-19 80 90 1-20 80 90 1-154 80 100 2-154 80 100 1-128 80 100 2-136 80 100 1-125 80 100 2-125 80 100 1-135 80 100 2-135 80 90 1-136 80 100 2-128 80 100 2-31 80 80 1-21 80 90 1-32 80 90 2-32 80 90 1-31 80 100 1-24 80 90 1-155 80 90 2-155 80 90 1-166 80 90 2-166 80 90 1-156 80 100 2-156 80 90 1-159 80 90 2-159 80 100 1-167 80 100 2-167 80 100 2-175 80 90 2-50 80 90 2-51 80 100 1-59 80 90 2-59 80 90 1-50 80 80 1-51 80 80 1-191 80 100 2-191 80 100 1-192 80 100 2-192 80 100 1-200 80 100 2-200 80 100 c: Pre-emergence action at 320 g/ha against ALOMY in % 1-398 320 100 1-399 320 100 1-123 320 100 2-123 320 100 3-123 320 90 1-126 320 90 2-126 320 100 3-126 320 90 1-124 320 100 2-124 320 90 3-124 320 90 1-152 320 100 2-152 320 100 3-152 320 80 2-153 320 90 1-153 320 100

TABLE-US-00007 TABLE 3 Example number Dosage [g/ha] AMARE a: Pre-emergence action at 20 g/ha against AMARE in % 1-398 20 90 1-399 20 90 1-123 20 90 2-123 20 90 3-123 20 100 1-126 20 80 2-126 20 90 3-126 20 90 1-124 20 90 2-124 20 90 3-124 20 90 1-152 20 100 2-152 20 100 3-152 20 100 2-153 20 100 3-153 20 100 1-153 20 100 1-19 20 100 1-20 20 80 1-154 20 90 2-154 20 100 1-400 20 90 1-144 20 90 1-128 20 100 2-136 20 100 1-125 20 100 2-125 20 100 1-135 20 100 2-135 20 100 1-136 20 90 2-128 20 100 1-401 20 100 2-31 20 100 1-21 20 100 1-32 20 90 2-32 20 100 2-399 20 90 1-31 20 100 2-21 20 100 1-24 20 100 1-40 20 100 1-155 20 100 2-155 20 100 1-166 20 100 2-166 20 100 1-156 20 100 2-156 20 100 1-159 20 100 2-159 20 100 1-167 20 100 2-167 20 100 1-175 20 80 2-175 20 100 2-340 20 100 2-50 20 90 2-51 20 90 1-59 20 100 2-59 20 80 1-50 20 90 1-51 20 80 2-191 20 100 1-192 20 80 2-192 20 100 1-200 20 90 2-200 20 100 b: Pre-emergence action at 80 g/ha against AMARE in % 1-395 80 100 1-398 80 100 1-399 80 100 1-123 80 100 2-123 80 100 3-123 80 100 1-126 80 90 2-126 80 100 3-126 80 100 1-124 80 90 2-124 80 100 3-124 80 100 1-152 80 100 2-152 80 100 3-152 80 100 2-153 80 100 3-153 80 100 1-153 80 100 1-19 80 100 2-19 80 100 1-20 80 90 1-154 80 100 2-154 80 100 1-400 80 100 1-144 80 100 2-144 80 100 1-128 80 100 2-136 80 100 2-398 80 100 1-125 80 100 2-125 80 100 1-135 80 100 2-135 80 100 1-136 80 100 2-128 80 100 1-401 80 100 2-31 80 100 1-21 80 100 1-32 80 100 2-32 80 100 2-399 80 100 1-31 80 100 2-21 80 100 1-24 80 100 1-40 80 100 1-155 80 100 2-155 80 100 1-166 80 100 2-166 80 100 1-156 80 100 2-156 80 100 1-159 80 100 2-159 80 100 1-167 80 100 2-167 80 100 1-175 80 100 2-175 80 100 1-402 80 100 2-340 80 100 2-50 80 100 2-51 80 90 1-59 80 100 2-59 80 100 1-50 80 100 1-51 80 100 1-191 80 100 2-191 80 100 1-192 80 100 2-192 80 100 1-200 80 100 2-200 80 100 c: Pre-emergence action at 320 g/ha against AMARE in % 1-395 320 100 1-398 320 100 1-399 320 100 1-123 320 100 2-123 320 100 3-123 320 100 1-126 320 100 2-126 320 100 3-126 320 100 1-124 320 100 2-124 320 100 3-124 320 100 1-152 320 100 2-152 320 100 3-152 320 100 2-153 320 100 3-153 320 100 1-153 320 100

TABLE-US-00008 TABLE 4 Example number Dosage [g/ha] AVEFA a: Pre-emergence action at 20 g/ha against AVEFA in % 1-154 20 80 2-154 20 80 b: Pre-emergence action at 80 g/ha against AVEFA in % 1-398 80 80 1-123 80 90 2-123 80 90 3-123 80 80 1-126 80 80 2-126 80 80 1-124 80 80 2-124 80 90 1-152 80 100 2-152 80 100 2-153 80 100 1-153 80 100 1-19 80 80 1-154 80 100 2-154 80 100 1-125 80 80 1-135 80 90 2-128 80 100 2-21 80 80 1-24 80 90 1-155 80 90 2-155 80 90 1-166 80 90 2-166 80 80 1-156 80 80 2-156 80 90 1-159 80 80 2-159 80 90 1-167 80 90 2-51 80 80 1-191 80 90 2-191 80 90 1-192 80 80 2-192 80 80 2-200 80 90 c: Pre-emergence action at 320 g/ha against AVEFA in % 1-398 320 90 1-399 320 90 1-123 320 100 2-123 320 100 3-123 320 100 1-126 320 100 2-126 320 100 3-126 320 100 1-124 320 100 2-124 320 100 3-124 320 100 1-152 320 100 2-152 320 100 3-152 320 100 2-153 320 100 3-153 320 90 1-153 320 100

TABLE-US-00009 TABLE 5 Example number Dosage [g/ha] CYPES a: Pre-emergence action at 20 g/ha against CYPES in % 1-123 20 80 2-124 20 100 1-153 20 100 b: Pre-emergence action at 80 g/ha against CYPES in % 1-395 80 100 1-398 80 80 1-123 80 100 3-123 80 80 2-126 80 80 3-126 80 100 1-124 80 80 2-124 80 100 3-124 80 80 1-152 80 90 2-152 80 80 3-152 80 80 2-153 80 100 3-153 80 80 1-153 80 100 c: Pre-emergence action at 320 g/ha against CYPES in % 1-395 320 100 1-398 320 90 1-399 320 90 1-123 320 100 2-123 320 80 3-123 320 90 1-126 320 90 2-126 320 90 3-126 320 100 1-124 320 90 2-124 320 100 3-124 320 90 1-152 320 100 2-152 320 100 3-152 320 90 2-153 320 100 3-153 320 80 1-153 320 100

TABLE-US-00010 TABLE 6 Example number Dosage [g/ha] ECHCG a: Pre-emergence action at 20 g/ha against ECHCG in % 1-123 20 90 2-123 20 80 1-124 20 80 1-153 20 100 2-154 20 80 b: Pre-emergence action at 80 g/ha against ECHCG in % 1-398 80 80 1-399 80 100 1-123 80 100 2-123 80 100 3-123 80 80 1-126 80 90 2-126 80 80 1-124 80 100 2-124 80 90 3-124 80 80 3-152 80 80 2-153 80 100 3-153 80 90 1-153 80 100 1-19 80 90 2-19 80 90 1-154 80 100 2-154 80 100 1-128 80 100 2-136 80 90 1-125 80 90 1-135 80 90 2-135 80 100 1-136 80 90 2-128 80 90 1-21 80 90 1-32 80 90 2-32 80 90 2-399 80 90 1-31 80 80 2-21 80 100 1-24 80 100 1-40 80 80 1-155 80 100 2-155 80 100 1-166 80 100 2-166 80 90 1-156 80 90 2-156 80 100 1-159 80 100 2-159 80 90 1-167 80 90 2-167 80 90 2-50 80 80 2-59 80 90 1-50 80 80 1-51 80 90 1-191 80 90 2-191 80 100 1-192 80 80 2-192 80 90 2-200 80 90 c: Pre-emergence action at 320 g/ha against ECHCG in % 1-395 320 100 1-398 320 100 1-399 320 100 1-123 320 100 2-123 320 100 3-123 320 100 1-126 320 100 2-126 320 100 3-126 320 80 1-124 320 100 2-124 320 100 3-124 320 100 1-152 320 100 2-152 320 100 3-152 320 100 2-153 320 100 3-153 320 100 1-153 320 100

TABLE-US-00011 TABLE 7 Example number Dosage [g/ha] MATIN a: Pre-emergence action at 20 g/ha against MATIN in % 1-398 20 90 3-123 20 80 1-126 20 80 2-126 20 80 1-124 20 80 2-124 20 80 3-124 20 80 1-152 20 100 2-152 20 90 3-152 20 80 2-153 20 100 3-153 20 80 1-153 20 90 1-154 20 80 2-154 20 90 1-144 20 90 1-128 20 80 2-136 20 80 1-135 20 90 2-135 20 90 1-136 20 90 2-128 20 100 2-31 20 90 1-21 20 80 2-32 20 80 2-399 20 90 2-21 20 90 1-24 20 90 1-155 20 90 2-155 20 80 1-166 20 90 2-166 20 80 1-156 20 90 2-156 20 100 1-159 20 90 2-159 20 90 1-167 20 80 2-167 20 100 1-175 20 90 2-175 20 90 2-50 20 90 2-51 20 90 2-59 20 90 1-50 20 80 1-191 20 80 2-191 20 90 2-192 20 100 2-200 20 90 b: Pre-emergence action at 80 g/ha against MATIN in % 1-398 80 100 1-399 80 90 1-123 80 90 2-123 80 100 3-123 80 90 1-126 80 100 2-126 80 90 3-126 80 90 1-124 80 90 2-124 80 90 3-124 80 90 1-152 80 100 2-152 80 100 3-152 80 100 2-153 80 100 3-153 80 100 1-153 80 100 1-19 80 90 2-19 80 90 1-20 80 100 1-154 80 90 2-154 80 100 1-400 80 90 1-144 80 100 2-144 80 100 1-128 80 90 2-136 80 100 2-398 80 100 1-125 80 100 2-125 80 100 1-135 80 100 2-135 80 100 1-136 80 100 2-128 80 100 1-401 80 90 2-31 80 100 1-21 80 100 1-32 80 100 2-32 80 100 2-399 80 100 1-31 80 100 2-21 80 100 1-24 80 100 1-40 80 90 1-155 80 100 2-155 80 100 1-166 80 90 2-166 80 100 1-156 80 100 2-156 80 100 1-159 80 100 2-159 80 100 1-167 80 100 2-167 80 100 1-175 80 90 2-175 80 100 1-402 80 90 2-340 80 90 2-50 80 90 2-51 80 100 1-59 80 90 2-59 80 100 1-50 80 90 1-51 80 90 1-191 80 100 2-191 80 100 1-192 80 100 2-192 80 100 1-200 80 100 2-200 80 100 c: Pre-emergence action at 320 g/ha against MATIN in % 1-395 320 100 1-398 320 100 1-399 320 100 1-123 320 90 2-123 320 100 3-123 320 100 1-126 320 100 2-126 320 100 3-126 320 100 1-124 320 100 2-124 320 100 3-124 320 90 1-152 320 100 2-152 320 100 3-152 320 100 2-153 320 100 3-153 320 100 1-153 320 100

TABLE-US-00012 TABLE 8 Example number Dosage [g/ha] PHBPU a: Pre-emergence action at 80 g/ha against PHBPU in % 1-124 80 80 2-124 80 80 1-153 80 90 2-154 80 80 1-136 80 90 2-128 80 80 2-32 80 80 1-166 80 90 1-167 80 80 1-200 80 80 2-200 80 90 b: Pre-emergence action at 320 g/ha against PHBPU in % 1-399 320 90 2-123 320 80 3-123 320 90 1-126 320 80 2-126 320 100 3-126 320 80 1-124 320 90 2-124 320 90 3-124 320 90 1-152 320 80 3-152 320 100 2-153 320 100 3-153 320 100 1-153 320 90

TABLE-US-00013 TABLE 9 Example number Dosage [g/ha] POLCO a: Pre-emergence action at 20 g/ha against POLCO in % 1-128 20 80 b: Pre-emergence action at 80 g/ha against POLCO in % 1-124 80 80 1-152 80 80 2-152 80 80 3-152 80 80 2-153 80 80 1-153 80 90 1-154 80 80 2-154 80 80 1-128 80 80 1-136 80 80 2-128 80 100 1-166 80 80 2-166 80 80 1-156 80 80 2-156 80 90 1-159 80 80 2-159 80 90 2-50 80 90 2-51 80 90 c: Pre-emergence action at 320 g/ha against POLCO in % 1-398 320 100 1-399 320 90 1-123 320 90 2-123 320 80 2-126 320 100 1-124 320 80 2-124 320 80 1-152 320 100 2-152 320 90 3-152 320 90 2-153 320 100 3-153 320 90 1-153 320 100

TABLE-US-00014 TABLE 10 Example number Dosage [g/ha] SETVI a: Pre-emergence action at 20 g/ha against SETVI in % 1-123 20 90 2-123 20 90 1-124 20 90 2-124 20 90 1-152 20 100 2-153 20 90 3-153 20 90 1-153 20 100 2-154 20 100 1-128 20 90 1-136 20 90 2-191 20 100 b: Pre-emergence action at 80 g/ha against SETVI in % 1-398 80 100 1-123 80 100 2-123 80 100 3-123 80 100 1-126 80 90 2-126 80 100 3-126 80 80 1-124 80 100 2-124 80 100 3-124 80 90 1-152 80 100 2-152 80 90 2-153 80 100 3-153 80 100 1-153 80 100 1-19 80 100 2-19 80 100 1-20 80 100 1-154 80 100 2-154 80 100 1-128 80 100 2-136 80 100 2-398 80 80 1-125 80 100 2-125 80 100 1-135 80 100 2-135 80 100 1-136 80 100 2-128 80 100 1-401 80 100 2-31 80 90 1-21 80 100 1-32 80 100 2-32 80 100 2-399 80 100 1-31 80 100 2-21 80 100 1-24 80 100 1-155 80 100 2-155 80 100 1-166 80 100 2-166 80 100 1-156 80 100 2-156 80 100 1-159 80 100 2-159 80 100 1-167 80 100 2-167 80 100 1-59 80 100 1-50 80 80 1-51 80 80 1-191 80 100 2-191 80 100 1-192 80 100 2-192 80 100 1-200 80 100 2-200 80 100 c: Pre-emergence action at 320 g/ha against SETVI in % 1-395 320 100 1-398 320 100 1-399 320 100 1-123 320 100 2-123 320 100 3-123 320 100 1-126 320 100 2-126 320 100 3-126 320 100 1-124 320 100 2-124 320 100 3-124 320 100 1-152 320 100 2-152 320 100 3-152 320 100 2-153 320 100 3-153 320 100 1-153 320 100

TABLE-US-00015 TABLE 11 Example number Dosage [g/ha] STEME a: Pre-emergence action at 20 g/ha against STEME in % 1-398 20 90 1-399 20 90 1-123 20 90 2-123 20 90 3-123 20 90 1-126 20 80 2-126 20 80 3-126 20 80 1-124 20 90 2-124 20 90 3-124 20 90 1-152 20 90 2-152 20 100 3-152 20 100 2-153 20 90 3-153 20 90 1-153 20 90 b: Pre-emergence action at 80 g/ha against STEME in % 1-398 80 100 1-399 80 90 1-123 80 90 2-123 80 100 3-123 80 100 3-126 80 80 1-124 80 90 2-124 80 90 3-124 80 100 1-152 80 100 2-152 80 100 3-152 80 100 2-153 80 100 3-153 80 100 1-153 80 90 c: Pre-emergence action at 320 g/ha against STEME in % 1-395 320 100 1-398 320 100 1-399 320 100 1-123 320 90 2-123 320 100 3-123 320 100 1-126 320 90 2-126 320 90 3-126 320 100 1-124 320 90 2-124 320 90 3-124 320 100 1-152 320 100 2-152 320 100 3-152 320 100 2-153 320 100 3-153 320 100 1-153 320 100

TABLE-US-00016 TABLE 12 Example number Dosage [g/ha] VERPE a: Pre-emergence action at 20 g/ha against VERPE in % 1-395 20 90 2-32 20 90 2-399 20 100 2-21 20 80 1-159 20 90 b: Pre-emergence action at 80 g/ha against VERPE in % 1-395 80 100 1-123 80 80 2-126 80 80 1-124 80 80 2-152 80 80 1-153 80 90 2-19 80 90 1-20 80 80 1-154 80 80 2-154 80 90 1-128 80 100 1-135 80 90 2-128 80 100 2-31 80 80 1-21 80 80 2-32 80 90 2-399 80 100 1-31 80 90 2-21 80 100 1-24 80 100 1-155 80 90 2-155 80 90 1-166 80 100 2-166 80 100 1-156 80 90 2-156 80 90 1-159 80 100 2-159 80 80 2-50 80 80 1-59 80 90 2-59 80 90 1-51 80 80 1-191 80 90 2-192 80 80 1-200 80 100 2-200 80 90 c: Pre-emergence action at 320 g/ha against VERPE in % 1-395 320 100 1-398 320 100 1-399 320 80 1-123 320 90 2-123 320 100 3-123 320 90 1-126 320 90 2-126 320 90 3-126 320 90 1-124 320 100 2-124 320 100 3-124 320 90 1-152 320 90 2-152 320 100 3-152 320 100 2-153 320 90 3-153 320 90 1-153 320 100

TABLE-US-00017 TABLE 13 Example number Dosage [g/ha] VIOTR a: Pre-emergence action at 20 g/ha against VIOTR in % 2-126 20 80 2-124 20 80 3-153 20 90 2-19 20 80 2-154 20 90 1-144 20 80 1-128 20 100 2-136 20 100 1-125 20 100 1-135 20 100 2-135 20 100 1-136 20 100 2-128 20 100 2-31 20 100 1-21 20 90 1-32 20 80 2-32 20 90 2-399 20 90 2-21 20 100 1-24 20 80 1-167 20 90 2-167 20 80 2-59 20 100 2-200 20 80 b: Pre-emergence action at 80 g/ha against VIOTR in % 1-395 80 80 1-398 80 80 1-399 80 100 2-123 80 90 3-123 80 80 1-126 80 100 2-126 80 100 3-126 80 90 1-124 80 100 2-124 80 80 3-124 80 80 1-152 80 100 3-152 80 90 2-153 80 100 3-153 80 100 1-153 80 100 1-19 80 100 2-19 80 100 1-20 80 100 1-154 80 100 2-154 80 100 1-144 80 100 2-144 80 100 1-128 80 100 2-136 80 100 2-398 80 100 1-125 80 100 2-125 80 100 1-135 80 100 2-135 80 100 1-136 80 100 2-128 80 100 2-31 80 100 1-21 80 100 1-32 80 100 2-32 80 100 2-399 80 100 1-31 80 100 2-21 80 100 1-24 80 100 1-40 80 100 1-155 80 100 2-155 80 100 1-166 80 100 2-166 80 100 1-156 80 100 2-156 80 100 1-159 80 100 2-159 80 100 1-167 80 100 2-167 80 100 1-175 80 90 2-175 80 90 2-51 80 80 2-59 80 100 1-51 80 90 1-191 80 100 2-191 80 80 1-192 80 100 2-192 80 100 1-200 80 100 2-200 80 100 c: Pre-emergence action at 320 g/ha against VIOTR in % 1-395 320 100 1-398 320 100 1-399 320 100 1-123 320 90 2-123 320 100 3-123 320 100 1-126 320 100 2-126 320 100 3-126 320 100 1-124 320 100 2-124 320 100 3-124 320 100 1-152 320 100 2-152 320 100 3-152 320 90 2-153 320 100 3-153 320 100 1-153 320 100

TABLE-US-00018 TABLE 14 Example number Dosage [g/ha] LOLRI a: Pre-emergence action at 80 g/ha against LOLRI in % 1-123 80 80 2-123 80 80 1-124 80 80 1-152 80 80 2-153 80 80 1-153 80 80 1-154 80 90 2-154 80 80 1-155 80 80 2-155 80 90 1-166 80 80 2-156 80 80 1-159 80 80 2-159 80 90 1-167 80 90 2-167 80 80 1-191 80 80 1-192 80 80 2-192 80 80 b: Pre-emergence action at 320 g/ha against LOLRI in % 1-398 320 90 1-123 320 100 2-123 320 100 3-123 320 80 1-126 320 90 2-126 320 90 3-126 320 80 1-124 320 100 2-124 320 90 3-124 320 80 1-152 320 100 2-152 320 100 2-153 320 90 1-153 320 90

TABLE-US-00019 TABLE 15 Example number Dosage [g/ha] HORMU a: Pre-emergence action at 80 g/ha against HORMU in % 1-123 80 90 2-123 80 80 3-123 80 80 1-126 80 80 1-124 80 90 2-124 80 80 1-152 80 90 1-153 80 80 b: Pre-emergence action at 320 g/ha against HORMU in % 1-398 320 100 1-399 320 90 1-123 320 100 2-123 320 100 3-123 320 100 1-126 320 100 2-126 320 100 1-124 320 90 2-124 320 90 3-124 320 80 1-152 320 100 2-152 320 80 2-153 320 90 1-153 320 100

TABLE-US-00020 TABLE 16 Example number Dosage [g/ha] DIGSA a: Pre-emergence action at 20 g/ha against DIGSA in % 2-19 20 100 1-154 20 100 2-154 20 100 1-400 20 100 1-128 20 100 2-136 20 90 1-125 20 100 2-135 20 80 1-136 20 90 2-128 20 90 1-401 20 90 2-31 20 90 1-21 20 100 1-32 20 90 2-32 20 100 2-399 20 90 1-31 20 100 2-21 20 100 1-24 20 100 b: Pre-emergence action at 80 g/ha against DIGSA in % 1-19 80 100 2-19 80 100 1-20 80 90 1-154 80 100 2-154 80 100 1-400 80 100 1-144 80 100 1-128 80 100 2-136 80 100 2-398 80 90 1-125 80 100 2-125 80 100 1-135 80 100 2-135 80 90 1-136 80 100 2-128 80 100 1-401 80 100 2-31 80 100 1-21 80 100 1-32 80 100 2-32 80 100 2-399 80 100 1-31 80 100 2-21 80 100 1-24 80 100 1-40 80 100

[0498] 2. Post-Emergence Herbicidal Action Against Harmful Plants

[0499] 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 equivalent 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 illustrative manner, the post-emergence herbicidal action of the compounds of the invention, the herbicidal activity being stated in percent.

TABLE-US-00021 TABLE 17 Example number Dosage [g/ha] ABUTH a: Post-emergence action at 5 g/ha against ABUTH in % 1-399 5 80 1-123 5 100 2-123 5 100 3-123 5 100 1-126 5 100 2-126 5 80 3-126 5 100 1-124 5 100 2-124 5 100 3-124 5 100 1-152 5 100 2-152 5 80 3-152 5 90 2-153 5 80 3-153 5 90 1-153 5 90 1-19 5 90 1-20 5 80 1-154 5 100 2-154 5 100 1-128 5 80 2-136 5 80 1-135 5 80 1-136 5 90 2-128 5 80 1-155 5 90 2-155 5 80 1-166 5 80 2-166 5 80 1-156 5 90 1-159 5 90 2-159 5 80 1-167 5 90 2-167 5 90 1-175 5 80 2-175 5 80 2-50 5 90 2-51 5 90 1-59 5 90 2-59 5 90 1-50 5 80 1-51 5 80 1-191 5 80 2-191 5 90 1-192 5 90 2-192 5 80 1-200 5 80 2-200 5 80 b: Post-emergence action at 20 g/ha against ABUTH in % 1-398 20 100 1-399 20 100 1-123 20 100 2-123 20 100 3-123 20 100 1-126 20 100 2-126 20 100 3-126 20 100 1-124 20 100 2-124 20 100 3-124 20 100 1-152 20 100 2-152 20 80 3-152 20 100 2-153 20 90 3-153 20 90 1-153 20 90 1-19 20 100 2-19 20 100 1-20 20 90 1-154 20 100 2-154 20 100 1-128 20 90 2-136 20 90 1-135 20 90 1-136 20 100 2-128 20 80 1-24 20 80 1-155 20 90 2-155 20 90 1-166 20 90 2-166 20 90 1-156 20 90 2-156 20 90 1-159 20 90 2-159 20 90 1-167 20 90 2-167 20 90 1-175 20 90 2-175 20 90 2-50 20 90 2-51 20 90 1-59 20 90 2-59 20 90 1-50 20 90 1-51 20 80 1-191 20 90 2-191 20 90 1-192 20 90 2-192 20 80 1-200 20 90 2-200 20 100;; c: Post-emergence action at 80 g/ha against ABUTH in % 1-395 80 100 1-398 80 100 1-399 80 100 1-123 80 100 2-123 80 100 3-123 80 100 1-126 80 100 2-126 80 100 3-126 80 100 1-124 80 100 2-124 80 100 3-124 80 100 1-152 80 100 2-152 80 80 3-152 80 100 2-153 80 100 3-153 80 90 1-153 80 90

TABLE-US-00022 TABLE 18 Example number Dosage [g/ha] ALOMY a: Post-emergence action at 5 g/ha against ALOMY in % 1-123 5 100 2-123 5 90 1-126 5 90 2-126 5 80 1-124 5 90 2-124 5 90 2-152 5 80 1-153 5 80 1-154 5 90 2-154 5 90 1-125 5 80 1-135 5 80 1-136 5 80 1-32 5 80 2-32 5 80 1-31 5 80 2-21 5 80 1-155 5 80 1-166 5 80 1-156 5 80 1-159 5 90 1-167 5 90 2-167 5 80 2-51 5 80 1-59 5 90 1-191 5 80 1-192 5 90 2-192 5 80 b: Post-emergence action at 20 g/ha against ALOMY in % 1-123 20 100 2-123 20 100 3-123 20 80 1-126 20 100 2-126 20 90 1-124 20 100 2-124 20 100 3-124 20 80 1-152 20 80 2-152 20 90 1-153 20 90 2-19 20 80 1-154 20 100 2-154 20 90 1-128 20 80 2-136 20 90 1-125 20 90 2-125 20 80 1-135 20 90 2-135 20 90 1-136 20 90 2-31 20 80 1-21 20 80 1-32 20 90 2-32 20 100 1-31 20 90 2-21 20 90 1-24 20 90 1-155 20 90 2-155 20 90 1-166 20 80 2-166 20 90 1-156 20 90 2-156 20 90 1-159 20 90 1-167 20 90 2-167 20 100 2-50 20 80 2-51 20 90 1-59 20 90 2-59 20 90 1-51 20 80 1-191 20 100 2-191 20 100 1-192 20 100 2-192 20 100 2-200 20 100 c: Post-emergence action at 80 g/ha against ALOMY in % 1-398 80 100 1-123 80 100 2-123 80 100 3-123 80 100 1-126 80 100 2-126 80 100 3-126 80 80 1-124 80 100 2-124 80 100 3-124 80 100 1-152 80 90 2-152 80 100 3-152 80 80 2-153 80 90 1-153 80 90

TABLE-US-00023 TABLE 19 Example number Dosage [g/ha] AMARE a: Post-emergence action at 5 g/ha against AMARE in % 1-398 5 80 1-399 5 100 1-123 5 100 2-123 5 100 3-123 5 100 1-126 5 100 2-126 5 100 3-126 5 100 1-124 5 100 2-124 5 100 3-124 5 100 1-152 5 100 2-152 5 100 3-152 5 100 2-153 5 100 3-153 5 90 1-153 5 100 2-19 5 80 1-154 5 90 2-154 5 90 1-144 5 90 2-144 5 90 1-128 5 100 2-136 5 100 1-125 5 80 2-125 5 90 1-135 5 80 2-135 5 80 1-136 5 100 1-32 5 90 2-32 5 100 1-31 5 90 2-21 5 100 1-40 5 80 1-155 5 100 2-155 5 100 1-166 5 100 2-166 5 100 1-156 5 100 2-156 5 100 1-159 5 100 2-159 5 100 1-167 5 100 2-167 5 100 1-175 5 100 2-175 5 100 2-50 5 100 2-51 5 90 1-59 5 100 2-59 5 100 1-50 5 90 1-51 5 100 1-191 5 100 2-191 5 100 1-192 5 100 2-192 5 100 1-200 5 100 2-200 5 100 b: Post-emergence action at 20 g/ha against AMARE in % 1-398 20 100 1-399 20 100 1-123 20 100 2-123 20 100 3-123 20 100 1-126 20 100 2-126 20 100 3-126 20 100 1-124 20 100 2-124 20 100 3-124 20 100 1-152 20 100 2-152 20 100 3-152 20 100 2-153 20 100 3-153 20 90 1-153 20 100 1-19 20 100 2-19 20 90 1-154 20 100 2-154 20 100 1-144 20 90 2-144 20 90 1-128 20 100 2-136 20 100 1-125 20 90 2-125 20 90 1-135 20 80 2-135 20 90 1-136 20 100 1-32 20 100 2-32 20 100 2-399 20 80 1-31 20 90 2-21 20 100 1-24 20 90 1-40 20 80 1-155 20 100 2-155 20 100 1-166 20 100 2-166 20 100 1-156 20 100 2-156 20 100 1-159 20 100 2-159 20 100 1-167 20 100 2-167 20 100 1-175 20 100 2-175 20 100 1-402 20 90 2-50 20 100 2-51 20 100 1-59 20 100 2-59 20 100 1-50 20 100 1-51 20 100 1-191 20 100 2-191 20 100 1-192 20 100 2-192 20 100 1-200 20 100 2-200 20 100 c: Post-emergence action at 80 g/ha against AMARE in % 1-395 80 80 1-398 80 100 1-399 80 100 1-123 80 100 2-123 80 100 3-123 80 100 1-126 80 100 2-126 80 100 3-126 80 100 1-124 80 100 2-124 80 100 3-124 80 100 1-152 80 100 2-152 80 100 3-152 80 100 2-153 80 100 3-153 80 100 1-153 80 100

TABLE-US-00024 TABLE 20 Example number Dosage [g/ha] AVEFA a: Post-emergence action at 5 g/ha against AVEFA in % 1-123 5 80 2-123 5 80 3-123 5 80 1-124 5 80 2-124 5 80 2-152 5 80 2-154 5 80 b: Post-emergence action at 20 g/ha against AVEFA in % 1-123 20 90 2-123 20 100 3-123 20 100 1-126 20 100 2-126 20 100 3-126 20 90 1-124 20 100 2-124 20 100 3-124 20 80 1-152 20 90 2-152 20 100 2-153 20 90 2-154 20 100 2-136 20 80 1-125 20 80 2-125 20 80 1-135 20 80 2-135 20 80 2-128 20 80 2-31 20 80 1-32 20 80 2-32 20 80 1-31 20 80 1-24 20 80 1-155 20 80 1-166 20 80 2-166 20 80 2-156 20 90 2-159 20 90 2-167 20 80 1-59 20 90 1-191 20 90 2-192 20 80 c: Post-emergence action at 80 g/ha against AVEFA in % 1-398 80 80 1-123 80 100 2-123 80 100 3-123 80 100 1-126 80 100 2-126 80 100 3-126 80 100 1-124 80 100 2-124 80 100 3-124 80 100 1-152 80 100 2-152 80 100 3-152 80 100 2-153 80 100 3-153 80 80 1-153 80 100

TABLE-US-00025 TABLE 21 Example number Dosage [g/ha] CYPES a: Post-emergence action at 5 g/ha against CYPES in % 1-123 5 80 2-123 5 80 b: Post-emergence action at 20 g/ha against CYPES in % 1-123 20 90 2-123 20 80 2-126 20 80 1-124 20 80 3-152 20 80 c: Post-emergence action at 80 g/ha against CYPES in % 1-123 80 90 2-123 80 90 1-126 80 80 2-126 80 90 1-124 80 80 2-124 80 90 3-124 80 80 1-152 80 80 2-152 80 80 3-152 80 80 1-153 80 90

TABLE-US-00026 TABLE 22 Example number Dosage [g/ha] ECHCG a: Post-emergence action at 5 g/ha against ECHCG in % 1-123 5 100 2-123 5 100 3-123 5 90 1-126 5 80 2-126 5 90 3-126 5 90 1-124 5 100 3-124 5 90 1-152 5 80 2-153 5 80 1-153 5 90 1-154 5 90 2-154 5 80 1-135 5 80 2-31 5 80 1-32 5 100 2-32 5 90 1-31 5 90 2-21 5 90 1-156 5 90 1-159 5 80 2-50 5 80 b: Post-emergence action at 20 g/ha against ECHCG in % 1-395 20 100 1-398 20 100 1-399 20 80 1-123 20 100 2-123 20 100 3-123 20 100 1-126 20 100 2-126 20 100 3-126 20 100 1-124 20 100 2-124 20 100 3-124 20 100 1-152 20 90 2-152 20 100 3-152 20 80 2-153 20 80 3-153 20 80 1-153 20 100 1-19 20 90 2-19 20 90 1-154 20 90 2-154 20 90 2-136 20 90 1-135 20 90 2-135 20 80 1-136 20 90 2-128 20 80 2-31 20 90 1-21 20 90 1-32 20 100 2-32 20 90 2-399 20 80 1-31 20 90 2-21 20 90 1-24 20 80 1-155 20 90 2-166 20 80 1-156 20 90 2-156 20 90 1-159 20 90 2-159 20 90 1-167 20 80 2-167 20 90 2-50 20 90 2-51 20 90 1-59 20 80 2-59 20 90 1-50 20 80 1-51 20 80 1-191 20 100 1-192 20 100 2-192 20 100 1-200 20 100 c: Post-emergence action at 80 g/ha against ECHCG in % 1-395 80 100 1-398 80 100 1-399 80 100 1-123 80 100 2-123 80 100 3-123 80 100 1-126 80 100 2-126 80 100 3-126 80 100 1-124 80 100 2-124 80 100 3-124 80 100 1-152 80 100 2-152 80 100 3-152 80 100 2-153 80 90 3-153 80 100 1-153 80 100

TABLE-US-00027 TABLE 23 Example number Dosage [g/ha] MATIN a: Post-emergence action at 5 g/ha against MATIN in % 1-123 5 80 2-123 5 90 3-123 5 90 1-126 5 80 2-126 5 80 3-126 5 80 2-124 5 90 3-124 5 90 2-152 5 80 2-153 5 90 3-153 5 80 1-153 5 90 1-154 5 80 2-154 5 80 2-128 5 80 2-31 5 80 2-32 5 80 2-21 5 80 1-24 5 90 2-155 5 80 1-166 5 80 2-166 5 80 1-156 5 80 2-156 5 90 1-159 5 80 2-159 5 80 2-59 5 80 b: Post-emergence action at 20 g/ha against MATIN in % 1-399 20 90 1-123 20 80 2-123 20 90 3-123 20 100 1-126 20 90 2-126 20 100 3-126 20 90 1-124 20 100 2-124 20 100 3-124 20 100 2-152 20 80 2-153 20 100 3-153 20 90 1-153 20 90 2-19 20 80 1-154 20 90 2-154 20 90 2-144 20 80 1-128 20 80 2-136 20 80 1-125 20 80 2-125 20 90 1-135 20 80 2-135 20 80 1-136 20 90 2-128 20 90 1-401 20 90 2-31 20 90 1-21 20 80 2-32 20 90 2-399 20 80 2-21 20 90 1-24 20 90 1-40 20 80 1-155 20 90 2-155 20 90 1-166 20 90 2-166 20 80 1-156 20 90 2-156 20 90 1-159 20 90 2-159 20 90 1-167 20 80 2-167 20 80 1-175 20 90 2-51 20 80 1-59 20 90 2-59 20 90 1-51 20 80 2-200 20 80;; c: Post-emergence action at 80 g/ha against MATIN in % 1-398 80 90 1-399 80 90 1-123 80 100 2-123 80 100 3-123 80 100 1-126 80 100 2-126 80 100 3-126 80 100 1-124 80 100 2-124 80 100 3-124 80 100 1-152 80 90 2-152 80 100 3-152 80 90 2-153 80 100 3-153 80 100 1-153 80 100

TABLE-US-00028 TABLE 24 Example number Dosage [g/ha] PHBPU a: Post-emergence action at 5 g/ha against PHBPU in % 2-123 5 80 3-123 5 80 1-126 5 90 2-126 5 90 1-124 5 80 2-124 5 80 3-124 5 90 1-152 5 80 3-153 5 80 1-153 5 80 1-154 5 80 2-128 5 80 1-32 5 80 1-31 5 90 1-155 5 80 2-155 5 80 1-166 5 90 2-166 5 80 1-156 5 80 2-156 5 80 b: Post-emergence action at 20 g/ha against PHBPU in % 1-398 20 80 2-123 20 90 3-123 20 90 1-126 20 90 2-126 20 100 3-126 20 90 1-124 20 90 2-124 20 90 3-124 20 90 1-152 20 90 2-152 20 80 3-152 20 80 2-153 20 80 3-153 20 80 1-153 20 90 1-20 20 90 1-154 20 90 2-154 20 80 1-128 20 90 1-136 20 80 2-128 20 80 1-401 20 80 2-31 20 90 1-32 20 90 2-399 20 90 1-31 20 90 2-21 20 90 1-155 20 80 2-155 20 80 1-166 20 90 2-166 20 90 1-156 20 90 2-156 20 80 1-159 20 90 2-167 20 90 1-50 20 80 1-51 20 90 2-191 20 80 1-192 20 80 2-192 20 80 1-200 20 90 2-200 20 80 c: Post-emergence action at 80 g/ha against PHBPU in % 1-398 80 80 1-399 80 90 1-123 80 100 2-123 80 100 3-123 80 90 1-126 80 100 2-126 80 100 3-126 80 100 1-124 80 90 2-124 80 90 3-124 80 100 1-152 80 90 2-152 80 80 3-152 80 100 2-153 80 90 3-153 80 90 1-153 80 90

TABLE-US-00029 TABLE 25 Example number Dosage [g/ha] POLCO a: Post-emergence action at 5 g/ha against POLCO in % 1-152 5 80 b: Post-emergence action at 20 g/ha against POLCO in % 3-152 20 90 2-153 20 90 2-154 20 90 2-32 20 80 1-24 20 100 c: Post-emergence action at 80 g/ha against POLCO in % 1-399 80 100 1-123 80 90 2-123 80 90 1-126 80 80 2-126 80 80 1-124 80 90 2-124 80 100 3-124 80 80 1-152 80 80 2-152 80 80 3-152 80 90 2-153 80 100 1-153 80 90

TABLE-US-00030 TABLE 26 Example number Dosage [g/ha] SETVI a: Post-emergence action at 5 g/ha against SETVI in % 1-123 5 100 2-123 5 100 3-123 5 100 1-126 5 100 2-126 5 100 1-124 5 100 2-124 5 100 3-124 5 90 1-152 5 100 1-19 5 100 2-19 5 80 1-154 5 100 2-154 5 90 2-31 5 80 1-32 5 80 1-31 5 90 2-21 5 80 1-155 5 80 2-155 5 80 1-166 5 80 2-166 5 90 1-156 5 90 1-159 5 100 2-167 5 90 2-51 5 80 1-59 5 90 2-59 5 90 1-51 5 80 2-191 5 100 1-192 5 100 2-192 5 100 1-200 5 80 2-200 5 100 b: Post-emergence action at 20 g/ha against SETVI in % 1-123 20 100 2-123 20 100 3-123 20 100 1-126 20 100 2-126 20 100 3-126 20 80 1-124 20 100 2-124 20 100 3-124 20 90 1-152 20 100 2-152 20 80 1-153 20 100 1-19 20 100 2-19 20 80 1-20 20 80 1-154 20 100 2-154 20 100 1-128 20 90 1-125 20 80 2-135 20 80 1-136 20 100 2-128 20 80 2-31 20 90 1-21 20 90 1-32 20 90 2-32 20 90 1-31 20 100 2-21 20 100 1-24 20 80 1-155 20 90 2-155 20 100 1-166 20 100 2-166 20 90 1-156 20 90 2-156 20 80 1-159 20 100 2-159 20 90 1-167 20 100 2-167 20 90 2-50 20 80 2-51 20 90 1-59 20 90 2-59 20 90 1-50 20 80 1-51 20 80 1-191 20 100 2-191 20 100 1-192 20 100 2-192 20 100 1-200 20 90 2-200 20 100 c: Post-emergence action at 80 g/ha against SETVI in % 1-395 80 90 1-398 80 100 1-123 80 100 2-123 80 100 3-123 80 100 1-126 80 100 2-126 80 100 3-126 80 100 1-124 80 100 2-124 80 100 3-124 80 100 1-152 80 100 2-152 80 100 3-152 80 100 2-153 80 100 1-153 80 100

TABLE-US-00031 TABLE 27 Example number Dosage [g/ha] STEME a: Post-emergence action at 5 g/ha against STEME in % 1-398 5 80 1-399 5 80 1-123 5 100 2-123 5 100 3-123 5 90 1-126 5 100 2-126 5 100 3-126 5 100 1-124 5 100 2-124 5 100 3-124 5 90 1-152 5 90 2-152 5 80 3-152 5 80 2-153 5 100 3-153 5 100 1-153 5 100 b: Post-emergence action at 20 g/ha against STEME in % 1-398 20 90 1-399 20 90 1-123 20 100 2-123 20 100 3-123 20 100 1-126 20 100 2-126 20 100 3-126 20 100 1-124 20 100 2-124 20 100 3-124 20 100 1-152 20 90 2-152 20 90 3-152 20 80 2-153 20 100 3-153 20 100 1-153 20 100 c: Post-emergence action at 80 g/ha against STEME in % 1-395 80 100 1-398 80 100 1-399 80 100 1-123 80 100 2-123 80 100 3-123 80 100 1-126 80 100 2-126 80 100 3-126 80 100 1-124 80 100 2-124 80 100 3-124 80 100 1-152 80 100 2-152 80 90 3-152 80 90 2-153 80 100 3-153 80 100 1-153 80 100

TABLE-US-00032 TABLE 28 Example number Dosage [g/ha] VERPE a: Post-emergence action at 5 g/ha against VERPE in % 1-123 5 80 1-124 5 80 2-152 5 80 2-154 5 80 1-156 5 80 1-159 5 80 b: Post-emergence action at 20 g/ha against VERPE in % 1-398 20 80 1-399 20 80 1-123 20 80 2-123 20 80 1-126 20 80 2-126 20 80 1-124 20 80 1-152 20 90 2-152 20 80 1-19 20 80 2-19 20 80 2-154 20 90 1-128 20 90 1-125 20 90 1-136 20 80 2-128 20 80 1-21 20 80 1-24 20 80 1-155 20 80 1-166 20 80 1-156 20 80 2-156 20 80 1-159 20 90 2-159 20 80 1-167 20 90 2-167 20 80 2-50 20 90 2-51 20 90 1-59 20 90 2-59 20 90 1-50 20 80 1-51 20 80 1-200 20 90 2-200 20 90 c: Post-emergence action at 80 g/ha against VERPE in % 1-398 80 90 1-399 80 90 1-123 80 100 2-123 80 100 1-126 80 80 2-126 80 90 3-126 80 90 1-124 80 100 2-124 80 100 3-124 80 80 1-152 80 90 2-152 80 80 3-152 80 80 2-153 80 80 1-153 80 80

TABLE-US-00033 TABLE 29 Example number Dosage [g/ha] VIOTR a: Post-emergence action at 5 g/ha against VIOTR in % 1-123 5 80 3-123 5 90 1-126 5 90 2-126 5 100 3-126 5 80 1-124 5 100 2-124 5 100 3-124 5 100 2-153 5 90 1-153 5 80 2-19 5 80 1-154 5 100 2-154 5 90 1-128 5 90 2-136 5 100 1-136 5 100 2-31 5 100 1-32 5 100 2-32 5 80 1-31 5 80 2-21 5 100 1-24 5 80 1-156 5 90 2-156 5 90 1-159 5 80 2-159 5 80 1-167 5 80 2-51 5 90 2-59 5 80 1-51 5 80 1-200 5 80 b: Post-emergence action at 20 g/ha against VIOTR in % 1-123 20 100 2-123 20 100 3-123 20 100 1-126 20 100 2-126 20 100 3-126 20 90 1-124 20 100 2-124 20 100 3-124 20 100 2-152 20 100 2-153 20 90 1-153 20 90 1-19 20 80 2-19 20 100 1-20 20 90 1-154 20 100 2-154 20 100 1-128 20 100 2-136 20 100 1-125 20 80 1-135 20 90 1-136 20 100 2-31 20 100 1-32 20 100 2-32 20 90 1-31 20 90 2-21 20 100 1-24 20 90 1-155 20 80 2-155 20 80 1-166 20 80 2-166 20 80 1-156 20 90 2-156 20 90 1-159 20 90 2-159 20 90 1-167 20 90 2-167 20 100 2-175 20 80 2-50 20 90 2-51 20 90 1-59 20 80 2-59 20 90 1-50 20 80 1-51 20 90 2-191 20 80 1-192 20 80 2-192 20 100 1-200 20 80 2-200 20 100 c: Post-emergence action at 80 g/ha against VIOTR in % 1-395 80 90 1-398 80 90 1-399 80 100 1-123 80 100 2-123 80 100 3-123 80 100 1-126 80 100 2-126 80 100 3-126 80 100 1-124 80 100 2-124 80 100 3-124 80 100 1-152 80 90 2-152 80 100 3-152 80 80 2-153 80 100 3-153 80 90 1-153 80 90

TABLE-US-00034 TABLE 30 Example number Dosage [g/ha] LOLRI a: Post-emergence action at 20 g/ha against LOLRI in % 1-123 20 80 1-124 20 90 2-124 20 90 1-152 20 90 b: Post-emergence action at 80 g/ha against LOLRI in % 1-123 80 90 2-123 80 100 1-126 80 90 2-126 80 80 1-124 80 100 2-124 80 100 1-152 80 100 2-152 80 90 2-153 80 80 1-153 80 90

TABLE-US-00035 TABLE 31 Example number Dosage [g/ha] HORMU a: Post-emergence action at 5 g/ha against HORMU in % 1-123 5 80 2-126 5 80 1-124 5 80 b: Post-emergence action at 20 g/ha against HORMU in % 1-123 20 80 2-123 20 90 3-123 20 90 1-126 20 100 2-126 20 90 1-124 20 90 2-124 20 90 3-124 20 80 1-153 20 80 c: Post-emergence action at 80 g/ha against HORMU in % 1-398 80 80 1-123 80 100 2-123 80 100 3-123 80 100 1-126 80 100 2-126 80 100 1-124 80 100 2-124 80 100 3-124 80 80 1-153 80 90

TABLE-US-00036 TABLE 32 Example number Dosage [g/ha] DIGSA a: Post-emergence action at 5 g/ha against DIGSA in % 1-19 5 90 1-154 5 90 2-154 5 90 1-135 5 90 2-135 5 80 1-32 5 90 2-32 5 90 1-31 5 80 2-21 5 80 1-24 5 100 1-155 5 80 2-155 5 80 1-166 5 90 2-166 5 80 b: Post-emergence action at 20 g/ha against DIGSA in % 1-19 20 90 2-19 20 90 1-20 20 80 1-154 20 90 2-154 20 90 1-125 20 100 2-125 20 90 1-135 20 90 2-135 20 90 1-32 20 90 2-32 20 90 1-31 20 90 2-21 20 90 1-24 20 100 1-40 20 90 1-155 20 80 2-155 20 80 1-166 20 90 2-166 20 90

Comparative Experiments

[0500] In the experiments that follow, herbicidal action of numerous inventive compounds and the structurally closest compounds known from D1 (WO 2012/028579 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.

TABLE-US-00037 TABLE 5 Herbicidal pre-emergence action Dosage Herbicidal action against Example No.: (g a.i./ha) AVEFA CYPES ECHCG SETVI ABUTH AMARE 1-123, inventive 80 90 100 100 100 100 100 4-251, from D1 80 0 20 20 20 50 70 Dosage Herbicidal action against Example No.: (g a.i./ha) AVEFA ALOMY ECHCG SETVI ABUTH VIOTR 1-154, inventive 80 100 100 100 100 100 100 4-251, from D1 80 0 0 20 20 50 0 Dosage Herbicidal action against Example No.: (g a.i./ha) ALOMY CYPES ECHCG SETVI MATIN AMARE 1-123, inventive 20 70 80 90 90 70 90 4-251, from D1 20 0 0 0 0 0 0 Dosage Herbicidal action against Example No.: (g a.i./ha) ALOMY AVEFA ECHCG SETVI ABUTH MATIN 2-154, inventive 20 80 80 80 100 100 90 5-251, from D1 20 0 0 30 30 70 70 Dosage Herbicidal action against Example No.: (g a.i./ha) ALOMY AVEFA ECHCG SETVI ABUTH 1-154, inventive 20 70 50 80 90 100 4-251, from D1 20 0 0 30 30 70

TABLE-US-00038 TABLE 6 Herbicidal post-emergence action Dosage Herbicidal action against Example No.: (g a.i./ha) ALOMY AVEFA SETVI ABUTH MATIN STEME 1-123, inventive 5 100 80 100 100 80 100 4-251, from D1 5 0 0 0 70 0 60 Dosage Herbicidal action against Example No.: (g a.i./ha) ALOMY PHBPU SETVI ABUTH MATIN VIOTR 1-154, inventive 5 90 80 100 100 80 100 4-251, from D1 5 0 40 0 70 0 20 Dosage Herbicidal action against Example No.: (g a.i./ha) ALOMY AVEFA SETVI MATIN PHBPU STEME 2-123, inventive 5 90 80 100 90 80 100 5-251, from D1 5 30 20 30 30 20 80 Dosage Herbicidal action against Example No.: (g a.i./ha) ALOMY AVEFA SETVI MATIN PHBPU VIOTR 2-154, inventive 5 90 80 90 80 70 80 5-251, from D1 5 30 20 30 30 20 60

SUBSTITUTED ISOPHTHALIC ACID DIAMIDES AND THEIR USE AS HERBICIDES

Inventors

Cpc classification

Classification Explorer

C07D271/08

CHEMISTRY; METALLURGY

Classification Explorer

A01P21/00

HUMAN NECESSITIES

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A01N43/713

HUMAN NECESSITIES

Classification Explorer

C07D403/12

CHEMISTRY; METALLURGY

Classification Explorer

A01P13/00

HUMAN NECESSITIES

Classification Explorer

C07D413/12

CHEMISTRY; METALLURGY

Classification Explorer

C07D257/06

CHEMISTRY; METALLURGY

International classification

Classification Explorer

A01N43/713

HUMAN NECESSITIES

Classification Explorer

C07D257/06

CHEMISTRY; METALLURGY

Classification Explorer

C07D403/12

CHEMISTRY; METALLURGY

Classification Explorer

A01P13/00

HUMAN NECESSITIES

Classification Explorer

A01P21/00

HUMAN NECESSITIES

Abstract

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Description