SPECIFICALLY SUBSTITUTED 3-PHENYL-5-SPIROCYCLOPENTYL-3-PYRROLIN-2-ONES AND THEIR USE AS HERBICIDES

Abstract

The present invention relates to novel herbicidally active pyrrolin-2-ones of the general formula (I) or agrochemically acceptable salts thereof and to their use for controlling broad-leaved weeds and weed grasses in crops of useful plants.

Claims

1. A compound comprising spirocyclopentylpyrrolin-2-one of formula (I) and/or an agrochemically acceptable salt thereof ##STR00048## X is C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy or halogen, Y is C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.3-C.sub.6-cycloalkyl or halogen, R.sup.1 is hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.2-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.4-haloalkenyl, C.sub.2-C.sub.6-alkynyl or C.sub.2-C.sub.6-haloalkynyl, R.sup.2 is hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy or C.sub.1-C.sub.6-haloalkoxy, R.sup.3 is hydrogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.3-C.sub.6-cycloalkyl or halogen, G is hydrogen, a leaving group L or a cation E, L is one of the radicals below ##STR00049## Wherein R.sup.4 represents (C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.3)-alkoxy-(C.sub.2-C.sub.4)-alkyl, R.sup.5 represents (C.sub.1-C.sub.4)-alkyl, R.sup.6 represents (C.sub.1-C.sub.4)-alkyl, an unsubstituted phenyl or a phenyl which is mono- or polysubstituted by halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy, nitro or cyano, R.sup.7, R.sup.7′independently of one another represent methoxy or ethoxy, R.sup.8, R.sup.9 each independently of one another represent methyl, ethyl, phenyl or together form a saturated 5-, 6- or 7-membered ring, or together form a saturated 5-, 6- or 7-membered heterocycle having an oxygen or sulfur atom, E represents an alkali metal ion, one ion equivalent of an alkaline earth metal, one ion equivalent of aluminum or one ion equivalent of a transition metal or a magnesium-halogen cation; represents an ammonium ion in which optionally one, two, three or all four hydrogen atoms may be replaced by identical or different radicals from the C.sub.1-C.sub.10-alkyl or C.sub.3-C.sub.7-cycloalkyl groups, where these independently of one another may each be mono- or polysubstituted by fluorine, chlorine, bromine, cyano, hydroxy or interrupted by one or more oxygen or sulfur atoms; represents a cyclic secondary or tertiary aliphatic or heteroaliphatic ammonium ion, optionally in each case morpholinium, thiomorpholinium, piperidinium, pyrrolidinium, or in each case protonated 1,4-diazabicyclo[1.1.2]octane (DABCO) or 1,5-diazabicyclo[4.3.0]undec-7-ene (DBU); represents a heteroaromatic ammonium cation, optionally in each case protonated pyridine, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, 2,4-dimethylpyridine, 2,5-dimethylpyridine, 2,6-dimethylpyridine, 5-ethyl-2-methylpyridine, collidine, pyrrole, imidazole, quinoline, quinoxaline, 1,2-dimethylimidazole, 1,3-dimethylimidazolium methylsulfate; or else may further represent a trimethylsulfonium ion.

2. The compound as claimed in claim 1, in which the radicals have the following meanings: X is C.sub.1-C.sub.6-alkoxy, bromine, chlorine or fluorine, Y is C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy or C.sub.3-C.sub.6-cycloalkyl, R.sup.1 is hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.2-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.1-C.sub.4-haloalkenyl, C.sub.2-C.sub.6-alkynyl or C.sub.2-C.sub.6-haloalkynyl, R.sup.2 is hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub.4-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy or C.sub.1-C.sub.6-haloalkoxy, R.sup.3 is hydrogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.3-C.sub.6-cycloalkyl or halogen, G is hydrogen, a leaving group L or a cation E, where L is one of the radicals below ##STR00050## wherein R.sup.4 is C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.3-alkoxy-C.sub.1-C.sub.4-alkyl, R.sup.5 is C.sub.1-C.sub.4-alkyl, R.sup.6 is C.sub.1-C.sub.4-alkyl, an unsubstituted phenyl or a phenyl which is mono- or polysubstituted by halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl or cyano, E is an alkali metal ion, one ion equivalent of an alkaline earth metal, one ion equivalent of aluminum, one ion equivalent of a transition metal, a magnesium halogen cation or an ammonium ion, in which optionally one, two, three or all four hydrogen atoms are replaced by identical or different radicals from the C.sub.1-C.sub.10-alkyl or C.sub.3-C.sub.7-cycloalkyl groups, each of which are independently mono- or polysubstituted by fluorine, chlorine, bromine, cyano, hydroxy.

3. The compound as claimed in claim 1, in which the radicals have the following meanings: X is C.sub.1-C.sub.6-alkoxy, bromine, chlorine or fluorine, Y is C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy or C.sub.3-C.sub.6-cycloalkyl, R.sup.1 is hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.2-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.1-C.sub.4-haloalkenyl, C.sub.2-C.sub.6-alkynyl or C.sub.2-C.sub.6-haloalkynyl, R.sup.2 is hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub.4-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy or C.sub.1-C.sub.6-haloalkoxy, R.sup.3 is hydrogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.3-C.sub.6-cycloalkyl or halogen, G is hydrogen, a leaving group L or a cation E, where L is one of the radicals below ##STR00051## wherein R.sup.4 is C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.3-alkoxy-C.sub.1-C.sub.4-alkyl, R.sup.5 is C.sub.1-C.sub.4-alkyl, E is an alkali metal ion, an ion equivalent of an alkaline earth metal, an ion equivalent of aluminum, an ion equivalent of a transition metal, a magnesium halogen cation or an ammonium ion, in which optionally one, two, three or all four hydrogen atoms are replaced by identical or different radicals from the groups C.sub.1-C.sub.10-alkyl or C.sub.3-C.sub.7-cycloalkyl substituted are.

4. The compound as claimed in claim 1, in which the radicals have the following meanings: X is methoxy, ethoxy, bromine, chlorine or fluorine, Y is methyl, ethyl, cyclopropyl, ethoxy, methoxy, R.sup.1 is hydrogen, ethyl, methyl, n-propyl, n-butyl, allyl, methoxymethyl or ethoxymethyl, R.sup.2 is hydrogen or methyl, R.sup.3 is hydrogen, methyl, ethyl, bromine, G is hydrogen, a leaving group L or a cation E, where L is one of the radicals below ##STR00052## wherein R.sup.4 is methyl, ethyl or i-propyl, R.sup.5 is methyl, ethyl, i-propyl or t-butyl, E is a sodium ion or a potassium ion.

5. A compound of formula (X) in which the radicals have the following meanings: ##STR00053## R.sup.3 is hydrogen or methyl, X is fluorine, chlorine or bromine, Y is methyl, ethyl, meth)oxy, ethoxy.

6. A process for preparing the compound of formula (I) an/or an agrochemically acceptable salt thereof as claimed in claim 1 comprising cyclizing a compound of formula (II) ##STR00054## in which R.sup.10 represents alkyl, optionally methyl or ethyl, optionally in the presence of a suitable solvent or diluent, with a suitable base, by formally eliminating the R.sup.10OH group.

7. An agrochemical composition comprising a) at least one compound of formula (I) and/or an agrochemically acceptable salt thereof as defined in claim 1 and b) one or more auxiliaries and additives customary in crop protection.

8. An agrochemical composition comprising a) at least one compound of formula (I) and/or an agrochemically acceptable salt thereof as defined in claim 1, b) one or more active agrochemical compounds other than component a), and optionally c) one or more auxiliaries and additives customary in crop protection.

9. A method of controlling one or more unwanted plants and/or for regulating the growth of plants, comprising applying an effective amount of at least one compound of formula (I) and/or an agrochemically acceptable salt thereof, as defined in claim 1 to the plants, seed and/or an area on which the plants grow.

10. A product comprising a compound of formula (I) and/or an agrochemically acceptable salt thereof, as defined in claim 1, as an herbicide or plant growth regulator.

11. The product as claimed in claim 10, wherein the compound of formula (I) and/or an agrochemically acceptable salt thereof is used for controlling one or more harmful plants and/or for regulating growth in one or more plant crops.

12. The product as claimed in claim 11, wherein the crop plant comprises one or more transgenic or nontransgenic crop plants.

Description

CHEMICAL EXAMPLES

Example I-11 3-(2-Bromo-6-methoxy-4-prop-1-ynylphenyl)-8-(ethoxymethyl)-4-hydroxy-1-azaspiro[4.4]non-3-en-2-one

[0227] ##STR00029##

[0228] To an initial charge of 1.00 g (2.14 mmol) of methyl 1-[[2-(2-bromo-6-methoxy-4-prop-1-ynyl-phenyl)acetyl]amino]-3-(ethoxymethyl)cyclopentanecarboxylate in 3.5 ml of dimethylformamide was added 0.52 g (4.71 mmol) of potassium tert-butoxide. The mixture was stirred at room temperature for 1 h, water was added and the mixture was washed with dichloromethane and acidified with 2N aqueous hydrochloric acid. The precipitated solid was filtered off with suction.

[0229] This gave 900 mg of a yellow solid (96% yield).

Example P-13 [3-(2-Bromo-6-methoxy-4-prop-1-ynyl-phenyl)-8-(ethoxymethyl)-2-oxo-1-azaspiro[4.4]non-3-en-4-yl] ethyl carbonate

[0230] ##STR00030##

[0231] To an initial charge of 0.80 g (1.47 mmol) of 3-(2-bromo-6-methoxy-4-prop-1-ynylphenyl)-8-(ethoxymethyl)-4-hydroxy-1-azaspiro[4.4]non-3-en-2-one and 0.29 g (2.94 mmol) of triethylamine in 10 ml of methylene chloride was added 0.19 g (1.76 mmol) of ethyl chloroformate dropwise. The mixture was left to stir at room temperature for 1 h. The mixture was washed with water, dried, the solvent was distilled off, and the residue was purified by chromatography.

[0232] This gave 700 mg of a light-colored solid (93% yield).

[0233] Analogously to this example and also according to the general details relating to the preparation, the following compounds are obtained:

##STR00031##

TABLE-US-00001 TABLE 1 Compounds of the general formula (Ib) Example Stereo- No. R.sup.1 R.sup.3 X Y chemistry .sup.1H NMR (400 MHz, δ in ppm) I-01 Me H OMe Cl cis D.sub.2O, NaOD δ = 1.45-1.56 (m, 2H), 1.77 (m, 1H), 2.00-2.08 (m, 2H), 2.28 (m, 1H), 2.41-2.47 (m, 1H), 3.40 (s, 3H), 3.40 (s, 1H) 3.54 (d, 2H), 3.78 (s, 3H), 7.13 (2, 1H), 7.31 (s, 1H) I-02 Et Me Me Cl trans d.sub.6-DMSO δ = 1.09-1.12 (t, 3H), 1.45-1.61 (m, 1H), 1.62-1.67 (m, 2H), 1.76-1.82 (m 1H), 1.91-1.94 (m 1H), 2.05 (s, 3H), 2.10 (s, 3H), 3.28-3.35 (m, 2H), 3.41- 3.45 (q, 2H), 7.22 (s, 1H), 7.27 (s, 1H), 7.93 (br, 1H), 10.98 (s, 1H) I-03 Et Me Et Cl trans d.sub.6-DMSO δ = 1.02 (t, 3H), 1.11 (t, 3H), 1.45-1.60 (m 1H), 1.61 (m, 2H), 1.75- 1.81 (m, 1H), 1.91 (m, 1H), 2.05 (s, 3H), 2.07-2.13 (m 1H), 2.40-2.45 (m, 3H), 3.33 (q, 2H), 3.43 (q, 2H), 7.21 (s, 1H), 7.28 (s, 1H), 7.92 (br, 1H), 10.96 (br, 1H) I-04 Me Me Et Cl trans d.sub.6-DMSO δ = 1.00-1.04 (t, 3H), 1.45-1.58 (m, 1H), 1.60-1.76 (m, 2H), 1.77-1.83 (m, 1H), 1.91-1.99 (m, 1H), 2.05 (s, 3H), 2.10-2.15 (m, 1H), 2.43 (q, 2H), 3.25 (s, 3H), 3.26 (m 2H), 7.21 (s, 1H), 7.29 (s, 1H), 7.93 (s, 1H), 10.96 (s, 1H) I-05 Et Me OMe Br trans d.sub.6-DMSO δ = 1.09-1.13 (t, 3H), 1.43-1.58 (m, 1H), 1.61-1.66 (m, 2H), 1.72-1.92 (m, 2H), 2.06 (s, 3H), 3.29 (m, 1H), 3.39-3.43 (q, 2H), 3.69 (s, 3H), 6.98 (s, 1H), 7.19 (s, 1H), 7.78 (s, 1H), 10.78 (s, 1H) I-06 Me Me Me Cl cis d.sub.6-DMSO δ = 1.45-168 (m, 3H), 1.84-1.94 (m 1H), 1.98-2.21 (m, 2H), 2.05 (s, 3H), 2.10 (s, 3H), 2.30-2.39 (m, 1H), 3.33 (m, 2H), 7.22 (s, 1H), 7.27 (s, 1H), 7.74 (br, 1H), 11.02 (br, 1H) I-07 Et Me OMe Cl trans D.sub.2O, NaOD δ δ = 1.18-1.23 (t, 3H), 1.50-1.58 (m 1H), 1.68-1.74 (m 1H), 1.80- 1.85 (m, 2H), 2.01-2.03 (m 1H), 2.05 (s, 3H)2.09-2.16 (m 1H), 2.48-2.53 (m, 1H), 3.49-3.54 (m 2H), 3.59-3.66 (q, 2H), 3.78 (s, 3H), 7.01 (s, 1H), 7.18 (s, 3H) I-08 Et H OMe Cl cis D.sub.2O, NaOD δ δ = 1.18-1.23 (t, 3H), 1.46-1.55 (m, 2H), 1.74-1.82 (m, 1H), 2.00- 2.08 (m, 2H), 2.26-2.32 (m, 1H), 2.39-2.48 (m, 1H), 3.50-.3.57 (m, 2H), 3.60- 3.65 (q, 2H), 3.78 (s, 3H), 7.13 (s, 1H), 7.31 (s, 1H) I-09 Et Me Me Cl cis d.sub.6-DMSO δ = 1.10-1.13 (t, 3H), 1.45-1.69 (m, 3H), 1.85-1.90 (m, 1H), 1.98-2.01 (m, 1H), 2.05 (s, 3H), 2.10 (s, 3H), 2.18-2.23 (m, 1H), 2.31-2.36 (m, 1H), 3.34- 3.37 (m, 2H), 3.38-3.46 (q, 2H), 7.22 (s, 3H), 7.27 (s, 3H), 7.72 (br, 1H) I-10 Me Me OMe Br cis D.sub.2O, NaOD δ δ = 1.16-1.20 (t, 3H), 1.46-1.58 (m, 2H), 1.75-1.82 (m, 1H), 2.00- 2.04 (m, 2H), 2.05 (s, 3H), 2.25-2.40 (m, 1H), 2.42-2.48 (m, 1H), 3.39 (s, 3H), 3.50-3.57 (m, 1H), 3.62-3.67 (q, 2H), 3.75 (s, 3H), 7.05 (s, 1H), 7.36 (s, 1H) I-11 Et Me OMe Br cis d.sub.6-DMSO δ = 1.09-1.13 (t, 3H), 1.44-1.52 (m, 2H), 1.54-1.62 (m 1H), 1.85-1.88 (m, 1H), 1.96-2.02 (m, 1H), 2.06 (s, 3H), 2.18-2.34 (m, 3H), 3.33-3.46 (m, 1H), 3.44-.3.46 (q, 2H), 3.69 (s, 3H), 6.98 (s, 1H), 7.19 (s, 1H), 7.58 (br, 1H), 10.8 (br, 1H) I-12 Me Me Me Cl trans d.sub.6-DMSO δ = 1.47-1.59 (m, 1H), 1.65 (m, 2H), 1.77-1.80 (m, 1H), 1.93-1.99 (m, 1H), 2.05 (s, 3H), 2.11 (s, 3H), 3.25 (s, 3H), 7.22 (s, 1H), 7.27 (s, 1H) I-13 Me H OMe Cl trans D.sub.2O, NaOD δ δ = 1.48-1.57 (m 1H), 1.69-1.85 (m, 3H), 2.00-2.14 (m, 2H), 2.46- 2.55 (m, 1H), 3.39 (s, 3H), 3.49 (m, 2H), 3.32 (s, 3H), 7.13 (s, 1H), 7.30 (s, 1H) I-14 Et H OMe Cl trans D.sub.2O, NaOD δ δ = 1.20 (t, 3H), 1.53 (m, 1H), 1.69-1.92 (m, 3H), 1.99-2.16 (m, 2H), 2.5 (m, 1H), 3.52 (m, 2H), 3.61 (q, 2H), 3.78 (s, 3H), 7.21 (s, 1H), 7.30 (s, 1H) I-15 Et Me Et Cl cis d.sub.6-DMSO δ = 1.0 (t, 3H), 1.1 (t, 3H), 1.5-1.9 (m, 4H), 2.0 (s, 3H), 2.2 (m, 1H), 2.3-2.4 (m, 2H), 3.4 (s, 3H), 3.5 (m, 4H), 7.1 (s, 1H), 7.25 (s, 1H), 7.8 (br, 1H) I-16 Me Me Et Cl cis d.sub.6-DMSO δ = 1.0 (t, 3H), 1.5-1.9 (m, 4H), 2.0 (s, 3H), 2.2 (m, 1H), 2.3-2.4 (m, 2H), 3.4 (s, 3H), 3.5 (m, 4H), 7.1 (s, 1H), 7.25 (s, 1H), 7.8 (br, 1H) I-17 Et Me Me Cl cis d.sub.6-DMSO δ = 1.1-1.2 (t, 3H), 1.4-1.9 (m, 5H), 2.01 (s, 3H), 2.1 (s, 3H), 2.2-2.7 (m, 2H), 3.4 (q, 2H), 3.5 (m, 2H), 7.22 (s, 1H), 7.27 (s, 1H), 7.73 (br, 1H), 7.93 (br, 1H) I-18 Me Me Br trans d.sub.6-DMSO δ = 1.4 (m, 1H), 1.4 (m, 2H), 1.8-1.9 (m, 2H), 2.0 (s, 3H), 2.1 (s, 3H), 3.2 (m, 4H), 3.3 (s, 3H), 7.25 (s, 1H), 7.44 (s, 1H), 7.92 (br, 1H), 10.9 (br, 1H) I-19 Me Me Me Br cis d.sub.6-DMSO δ = 1.3 (m, 2H), 1.4 (m, 1H), 1.8-1.9 (m, 1H), 2.0 (s, 3H), 2.1 (s, 3H), 2.2 (m, 2H), 3.3 (s, 3H), 3.4 (m, 2H), 7.25 (s, 1H), 7.44 (s, 1H), 7.74 (br, 1H), 10.9 (br, 1H) I-20 Et Me Me Br trans d.sub.6-DMSO δ = 1.1 (t, 3H), 1.4-1.9 (m, 5H), 2.0 (s, 3H), 2.1 (s, 3H), 2.2-2.3 (m, 2H), 3.4 (q, 2H), 3.5 (m, 2H), 7.25 (br, 1H), 7.44 (s, 1H), 7.98 (s, 1H), 10.96 (br, 1H) I-21 Et Me Me Br cis d.sub.6-DMSO δ = 1.1 (t, 3H), 1.4-1.9 (m, 4H), 2.0 (s, 3H), 2.1 (s, 3H), 2.2-2.3 (m, 2H), 3.4 (q, 2H), 3.5 (m, 2H), 7.25 (br, 1H), 7.44 (s, 1H), 7.73 (s, 1H), 10.98 (br, 1H) I-22 Me Me Et Br cis d.sub.6-DMSO δ = 1.0 (t, 3H), 1.4-1.6 (m, 3H), 1.8 (m, 1H), 2.1 (s, 3H), 2.2-2.4 (m, 1H), 3.3 (s, 3H), 3.4 (q, 2H), 7.1 (br, 1H), 7.5 (s, 1H), 7.81 (s, 1H), 10.9 (br, 1H) I-23 Me Me Et Br trans d.sub.6-DMSO δ = 1.0 (t, 3H), 1.4-1.6 (m, 3H), 1.8 (m, 1H), 2.1 (s, 3H), 2.2-2.4 (m, 1H), 3.3 (s, 3H), 3.4 (q, 2H), 7.1 (br, 1H), 7.5 (s, 1H), 7.99 (s, 1H), 10.9 (br, 1H) I-24 Et Me Et Br cis d.sub.6-DMSO δ = 1.1 (t, 3H), 1.2 (t, 3H), 1.4-1.7 (m, 3H), 1.8 (m, 1H), 2.1 (s, 3H), 2.2-2.4 (m, 2H), 3.4 (q, 2H), 3.5 (q, 2H), 7.11 (br, 1H), 7.5 (s, 1H), 7.79 (s, 1H) I-25 Et Me Et Br trans d.sub.6-DMSO δ = 1.1 (t, 3H), 1.2 (t, 3H), 1.4-1.7 (m, 3H), 1.8 (m, 1H), 2.1 (s, 3H), 2.1 (m, 1H), 3.3 (q, 2H), 3.4 (q, 2H), 7.11 (br, 1H), 7.5 (s, 1H), 7.99 (s, 1H), 10.9 (br, 1H) I-30 Et Me OMe Me cis d.sub.6-DMSO δ = 1.1 (t, 3H), 1.4-1.9 (m, 4H), 2.0(s, 3H), 2.3-2.4 (m, 2H), 2.5 (s, 3H), 3.4 (m, 2H), 3.5 (q, 2H), 3.6 (s, 3H), 6.78 (br, 1H), 6.88 (s, 1H), 7.57 (s, 1H), 10.85 (br, 1H) I-31 Me Me OMe Me trans d.sub.6-DMSO δ = 1.4-1.9 (m, 4H), 2.0 (s, 3H), 2.5 (m, 2H), 3.2 (m 2H), 3.3 (s, 3H), 3.6 (s, 3H), 6.78 (br, 1H), 6.88 (s, 1H), 7.78 (s, 1H), 10.55 (br, 1H) I-32 Et Me OMe Me trans d.sub.6-DMSO δ = 1.1 (t, 3H), 1.4-1.9 (m, 4H), 2.0(s, 3H), 2.3-2.4 (m, 2H), 2.5 (s, 3H), 3.4 (m, 2H), 3.5 (q, 2H), 3.6 (s, 3H), 6.78 (br, 1H), 6.88 (s, 1H), 7.78 (s, 1H), 10.85 (br, 1H) I-33 Me Me OMe Me cis d.sub.6-DMSO δ = 1.4-1.6 (m, 3H), 1.9 (m, 1H), 2.0 (s, 3H), 2.3-2.4 (m, 2H), 3.3 (s, 3H), 3.4 (m, 2H), 3.5 (s, 3H), 6.78 (br, 1H), 6.98 (s, 1H), 7.59 (s, 1H), 10.5 (br, 1H) I-34 Me Me F Me cis d.sub.6-DMSO δ = 1.4-1.6 (m, 3H), 1.9 (m, 1H), 2.0 (s, 3H), 2.2 (s, 3H), 2.3-2.4 (m, 2H), 3.4 (m, 2H), 3.5 (s, 3H), 6.98 (br, 1H), 7.09 (s, 1H), 7.79 (s, 1H), 11.08 (br, 1H) I-35 Et Me F Me cis d.sub.6-DMSO δ = 1.1 (t, 3H), 1.4-1.6 (m, 3H), 1.9 (m 1H), 2.0 (s, 3H), 2.2 (s, 3H), 2.4-2.45 (m, 2H), 3.4 (m, 2H), 3.5 (q, 2H), 6.99 (br, 1H), 7.09 (s, 1H), 7.78 (s, 1H), 11.07 (br, 1H) I-36 Me Me F Me trans d.sub.6-DMSO δ = 1.4-1.9 (m, 4H), 2.0 (s, 3H), 2.2 (s, 3H), 2.5 (m, 2H), 3.4 (m, 2H), 3.5 (s, 3H), 6.98 (br, 1H), 7.09 (s, 1H), 7.79 (s, 1H), 11.05 (br, 1H) I-37 Et Me F Me trans d.sub.6-DMSO δ = 1.1 (t, 3H), 1.4-1.9 (m 4H), 2.0 (s, 3H), 2.2 (s, 3H), 3.4 (m, 2H), 3.5 (q, 2H), I-40 Me Me F OMe trans d.sub.6-DMSO δ = 1.4-1.9 (m, 4H), 2.0 (s, 3H), 2.1-2.3 (m, 2H), 3.4 (m, 2H), 3.5 (s, 3H), 3.7 (s, 3H), 6.78 (br, 1H), 6.82 (s, 1H), 7.84 (s, 1H) I-41 Me Me F OMe cis d.sub.6-DMSO δ = 1.4-1.9 (m, 4H), 2.0 (s, 3H), 2.1-2.3 (m, 2H), 3.4 (m, 2H), 3.5 (s, 3H), 3.7 (s, 3H), 6.78 (br, 1H), 6.86 (s, 1H), 7.66 (s, 1H) I-42 Et Me F OMe cis D.sub.2O, NaOD δ: 0.9 (t, 3H), 1.2-1.7 (m, 4H), 1.8 (s, 3H), 2.0-2.1 (m, 2H), 3.3 (m, 2H), 3.4 (q, 2H), 3.5 (s, 3H), 6.59 (s, 1H), 6.62 (s, 1H), 6.64 (s, 1H) I-43 Et Me F OMe trans d6-DMSO δ = 1.1 (t, 3H), 1.4-1.9 m 4H), 2.0 (s, 3H), 2.4 (m, 1H), 3.3 (m, 2H), 3.4 (q, 2H), 3.7 (s, 3H), 6.82 (br, 1H), 6.82 (s, 1H), 7.84 (s, 1H), 10.81 (br, 1H) I-44 allyl Me Cl Me cis d.sub.6-DMSO δ = 1.4-1.9 (m, 4H), 2.0 (s, 3H), 2.1 (s, 3H), 2.3 (m, 1H), 2.4 (m, 1H), 3.4 (m, 2H), 3.95 (dt, 2H), 5.28 (dq, 2H), 5.98 (m, 1H), 7.22 (s, 1H), 7.27 (s, 1H), 7.75 (br, 1H), 11.0 (br, 1H) I-45 allyl Me OMe Me trans d.sub.6-DMSO δ = 1.4-1.9 (m, 4H), 2.0 (s, 3H), 2.4 (m, 2H), 3.4 (m, 2H), 3.4 (s, 3H), 3.6 (s, 3H), 4.0 (m, 2H), 5.2 (dt, 2H), 5.9 (m, 1H), 6.78 (br, 1H), 6.84 (s, 1H), 7.78 (s, 1H), 10.88 (br, 1H) I-46 allyl Me Cl Me trans d.sub.6-DMSO δ = 1.4-1.9 (m, 4H), 2.0 (s, 3H), 2.1 (s, 3H), 2.5 (m, 2H), 3.4 (m, 2H), 3.95 (dt, 2H), 5.28 (dq, 2H), 5.98 (m, 1H), 7.22 (s, 1H), 7.27 (s, 1H), 7.94 (br, 1H), 11.0 (br, 1H) I-47 allyl Me OMe Me cis d.sub.6-DMSO δ = 1.4-1.9 (m, 3H), 2.0 (s, 3H), 2.2-2.4 (m, 2H), 3.4 (s, 3H), 3.6 (s, 3H), 4.0 (dt, 2H), 5.28 (dq, 2H), 5.9 (m, 1H), 6.78 (s, 1H), 6.88 (s, 1H), 7.60 (s, 1H), 10.52 (br, 1H) I-50 2- Me Cl Me trans d.sub.6-DMSO δ = 1.4-1.9 (m, 4H), 2.0 (s, 3H), 2.1 (s, 3H), 2.5 (m, 2H), 3.3 (s, 3H), methoxy- 3.4 (s, 3H), 3.4-3.5 (m, 4H), 7.22 (s, 1H), 7.27 (s, 1H), 7.94 (br, 1H) ethyl I-51 2- Me Cl Me cis d6-DMSO δ = 1.4-1.9 (m, 4H), 2.0 (s, 3H), 2.1 (s, 3H), 2.3 (m 1H), 2.4 (m, 1H), methoxy- 3.3 (s, 3H), 3.4 (s, 3H), 3.4-3.5 (m, 4H), 7.22 (s, 1H), 7.27 (s, 1H), 7.72 (br, 1H) ethyl I-52 2- Me OMe Me trans d.sub.6-DMSO δ = 1.5-1.9 (m, 4H), 2.0 (s, 3H), 3.2 (m, 2H), 3.3 (s, 3H), 3.5 (m, 4H), methoxy- 3.7 (s, 3H), 6.78 (br, 1H), 6.79 (s, 1H), 6.88 (s, 1H), 7.78 (br, 1H), 10.5 (br, 1H) ethyl I-54 allyl Me OMe F cis D.sub.2O, NaOD δ: 1.5 (m, 2H), 1.7 (m, 1H), 2.0 (m, 2H), 2.0 (s, 3H), 2.4 (m, 1H), 2.5 (m, 1H), 3.5 (m, 2H), 3.6 (s, 3H), 4.1 (m, 2H), 5.27 (qd, 1H), 5.38 (qd, 1H), 5.95 (m, 1H), 6.85 (s, 1H), 6.87 (s, 1H), 6.91 (s, 1H) I-55 allyl Me OMe F trans D.sub.2O, NaOD δ: 1.5 (m, 1H), 1.7 (m, 3H), 2.0 (m, 1H), 2.0 (s, 3H), 2.5 (m, 2H), 3.5 (m, 2H), 3.6 (s, 3H), 4.1 (m, 2H), 5.27 (qd, 1H), 5.38 (qd, 1H), 5.95 (m, 1H), 6.85 (s, 1H), 6.87 (s, 1H), 6.91 (s, 1H) I-56 propyl Me OMe F trans D.sub.2O, NaOD δ: 0.9 (t, 3H), 1.5-1.9 (m, 4H), 2.0 (s, 3H), 2.1 (m, 1H), 2.5 (m, 1H), 3.5 (m, 4H), 3.8 (s, 3H), 6.85 (s, 1H), 6.88 (s, 1H), 6.91 (s, 1H) I-57 propyl Me OMe F cis D.sub.2O, NaOD δ: 0.9 (t, 3H), 1.5-1.7 (m, 4H), 1.8 (m, 1H), 1.9 (m, 1H), 2.0 (s, 3H), 2.3 (m, 1H), 2.5 (m, 1H), 3.5 (m, 4H), 3.78 (s, 3H), 6.85 (s, 1H), 6.88 (s, 1H), 6.91 (s, 1H) I-58 propyl Me OMe Me cis D.sub.2O, NaOD δ: 0.9 (t, 3H), 1.5-1.9 (m, 4H), 2.0 (s, 3H), 2.1 (s, 3H), 2.4 (m, 1H), 2.5 (m, 1H), 3.5 (m, 4H), 3.7 (s, 3H), 6.92 (s, 1H), 7.00 (s, 1H) I-59 propyl Me OMe Me trans D.sub.2O, NaOD δ: 0.9 (t, 3H), 1.5-1.9 (m, 4H), 2.0 (m, 1H), 2.0 (s, 3H), 2.1 (s, 3H), 2.5 (m, 1H), 3.5 (m, 2H), 3.7 (s, 3H), 6.92 (s, 1H), 7.0 (s, 1H) I-63 Et Me Br OEt trans D.sub.2O, NaOD δ: 1.2 (t, 3H), 1.3 (t, 3H), 1.5 (m, 2H), 1.7 (m, 1H), 2.0 (m, 2H), 2.0 (s, 3H), 2.2 (m, 1H), 2.5 (m, 1H), 3.4 (d, 2H), 3.6 (q, 2H), 4.0 (q, 2H), 7.05 (s, 1H), 7.37 (s, 1H) I-64 Et Me Br OEt cis D.sub.2O, NaOD δ: 1.1 (t, 3H), 1.2 (t, 3H), 1.5 (m, 2H), 1.7 (m, 1H), 2.0 (m, 2H), 2.0 (s, 3H), 2.4 (m, 1H), 2.5 (m, 1H), 3.4 (d, 2H), 3.6 (q, 2H), 4.0 (q, 2H), 7.05 (s, 1H), 7.37 (s, 1H) I-66 Me Me Br OEt cis D.sub.2O, NaOD δ: 1.2 (t, 3H), 1.5 (m, 2H), 1.7 (m, 1H), 1.9 (m, 2H), 2.0 (s, 3H), 2.4 (m, 1H), 2.5 (m, 1H), 3.4 (s, 3H), 3.5 (d, 2H), 4.0 (q, 2H), 7.05 (s, 1H), 7.37 (s, 1H) I-67 allyl Me Me Br trans d.sub.6-DMSO δ = 1.5-1.9 (m, 4H), 2.0 (s, 3H), 2.1 (s, 3H), 3.4 (m, 4H), 4.0 (m, 2H), 5.22 (qd, 1H), 5.38 (qd, 1H), 5.96 (m, 1H), 7.25 (s, 1H), 7.44 (s, 1H), 7.93 (br, 1H) I-68 propyl Me Cl Me cis d.sub.6-DMSO δ = 0.9 (t, 3H), 1.5-1.9 (m, 4H), 2.0 (s, 3H), 2.1 (s, 3H), 2.4 (m, 2H), 3.4 (m, 4H), 7.22 (s, 1H), 7.27(s, 1H), 7.73 (br, 1H) I-69 Me Me Br OEt trans D.sub.2O, NaOD δ: 1.3 (t, 3H), 1.5 (m, 1H), 1.6-1.9 (m, 3H), 2.0 (s, 3H), 2.1 (m, 1H), 2.5 (m, 1H), 3.4 (s, 3H), 3.5 (m, 2H), 4.0 (q, 2H), 7.05 (s, 1H), 7.37 (s, 1H) I-70 allyl Me Me Br cis d.sub.6-DMSO δ = 1.5-1.9 (m, 4H), 2.0 (s, 3H), 2.1 (s, 3H), 2.3-2.5 (m, 2H), 3.4 (m, 4H), 4.0 (m, 2H), 5.22 (qd, 1H), 5.38 (qd, 1H), 5.95 (m, 1H), 7.25 (s, 1H), 7.44 (s, 1H), 7.74 (br, 1H) I-71 propyl Me Cl Me trans d.sub.6-DMSO δ = 0.9 (t, 3H), 1.5-1.9 (m, 4H), 2.0 (s, 3H), 2.1 (s, 3H), 3.4 (m, 4H), 7.22 (s, 1H), 7.27 (s, 1H), 7.93 (br, 1H) I-72 Me Me Cl OMe trans D.sub.2O, NaOD δ: 1.5-1.9 (m, 3H), 2.0 (s, 3H), 2.1 (m, 1H), 2.4 (m, 1H), 2.5 (m, 1H), 3.4 (s, 3H), 3.5 (m, 2H), 3.7 (s, 3H), 7.01 (s, 1H), 7.18 (s, 1H) I-73 Me Me Cl OMe cis D.sub.2O, NaOD δ: 1.5-1.9 (m, 4H), 2.0 (s, 3H), 2.4 (m, 1H), 2.5 (m, 1H), 3.4 (s, 3H), 3.5 (m, 2H), 3.7 (s, 3H), 7.01 (s, 1H), 7.18 (s, 1H) I-74 prop-2- Me F OMe cis D.sub.2O, NaOD δ: 1.5 (m, 2H), 1.6 (m, 1H), 2.0 (m, 2H), 2.1 (s, 3H), 2.4 (m, 1H), yn-1-yl 2.5 (m, 1H), 3.6 (d, 2H), 3.7 (s, 3H), 4.2 (s, 2H), 6.85 (s, 1H), 6.88 (s, 1H), 6.91 (s, 1H) I-75 prop-2- Me F OMe trans D.sub.2O, NaOD δ: 1.5 (m, 1H), 1.6-1.7 (m, 3H), 2.0 (m, 1H), 2.1 (s, 3H), 2.5 (m, yn-1-yl 1H), 3.6 (d, 2H), 3.7 (s, 3H), 4.3 (s, 2H), 6.85 (s, 1H), 6.88 (s, 1H), 6.91 (s, 1H) I-76 prop-2- Me Me OMe cis D.sub.2O, NaOD δ: 1.5 (m, 2H), 1.7 (m, 1H), 2.0 (m, 2H), 2.1 (s, 3H), 2.2 (s, 3H), 2.4, yn-1-yl (m, 1H), 2.5 (m, 1H), 3.6 (d, 2H), 3.7 (s, 3H), 4.2 (s, 2H), 6.92 (s, 1H), 7.00 (s, 1H) I-77 prop-2- Me Me OMe trans D.sub.2O, NaOD δ: 1.5 (m, 2H), 1.6-1.9 (m, 2H), 2.0 (s, 3H), 2.1 (m, 1H), 2.2 (s, 3H), yn-1-yl 2.5 (m, 1H), 3.6 (m, 2H), 3.7 (s, 3H), 4.2 (s, 2H), 6.90 (s, 1H), 7.00 (s, 1H) I-78 prop-2- Me Cl Me trans d.sub.6-DMSO δ = 1.4-1.9 (m, 5H), 2.0 (s, 3H), 2.1 (s, 3H), 3.2 (s, 3H), 3.5 (m, 2H), yn-1-yl 4.0 (s, 1H), 7.22 (s, 1H), 7.27 (s, 1H), 7.94 (br, 1H) I-79 prop-2- Me Cl Me cis d.sub.6-DMSO δ = 1.4-1.9 (m, 4H), 2.0 (s, 3H), 2.1 (s, 3H), 2.3-2.4 (m, 2H), 3.2 (s, yn-1-yl 3H), 3.5 (m, 2H), 4.0 (s, 1H), 7.22 (s, 1H), 7.27 (s, 1H), 7.77 (br, 1H) I-81 Me Me OMe Br trans d.sub.6-DMSO δ = 1.4-1.9 (m, 4H), 2.0 (s, 3H), 2.4 (m, 2H), 3.2 (s, 3H), 3.3 (m, 2H), 3.7 (s, 3H), 7.0 (s, 1H), 7.2 (s, 1H), 7.8 (br, 1H)

##STR00032##

TABLE-US-00002 TABLE 2 Compounds of the general formula (Ic) Example Stereo- No. G R.sup.1 R.sup.3 X Y chemistry .sup.1H NMR (400 MHz, CDCl.sub.3 δ in ppm) P-01 —CO.sub.2Et Et Me OMe Br trans 1.17 (t, 3H), 1.21 (t, 3H), 1.61-1.68 (m, 1H), 1.88-2.03 (m, 4H), 2.05 (s, 3H), 2.22-2.30 (m, 1H), 2.33-2.51 (m 1H), 3.38 (m, 2H), 3.49 (q, 2H), 3.78 (s, 3H), 4.05 (q, 2H), 6.87 (s, 1H), 7.25 (s, 1H) P-02 —CO.sub.2Et Me H OMe Cl cis 1.18 (t, 3H), 1.71-1.87 (m, 3H), 1.98-2.18 (m 2H), 2.41-2.52 (m 2H), 3.35- 3.45 (m 2H), 3.40 (s, 3H), 3.81 (s, 3H), 4.08 (q, 2H), 6.92 (s, 1H), 7.17 (s, 1H) P-03 —COiPr Et Me Me Cl trans 1.02-1.12 (d, 6H), 1.16-1.21 (t, 3H), 1.56-1.64 (m, 1H), 1.76-2.00 (m, 4H), 2.03 (s, 3H), 2.05-2.10 (m, 1H), 2.27 (s, 3H), 2.46-2.53 (m, 1H), 2.57-2.66 (hept, 1H), 3.33-3.40 (m, 2H), 3.44-3.51 (q, 2H), 6.76 (br, NH), 7.15 (s, 1H), 7.24 (s, 1H) P-04 —COiPr Me Me OMe Br cis 1.17 (d, 6H), 1.66-1.80 (m, 2H), 1.81-2.10 (m, 2H), 2.04 (s, 3H), 2.26-2.49 (m, 2H), 2.58-2.67 (m, 1H), 3.34-3.47 (m, 2H), 3.39 (s, 3H), 3.78 (s, 3H), 6.85 (br, 1H), 7.19 (s, 1H), 7.22 (s, 1H) P-05 —CO.sub.2Et Et Me OMe Br cis 1.17 (t, 3H), 1.29 (t, 3H), 1.68-1.73 (m, 1H), 1.83-1.90 (m, 2H), 1.98-2.13 (m, 2H), 2.04 (s, 3H), 2.38-2.53 (m, 2H), 3.39-3.44 (m, 2H), 3.51 (q, 2H), 3.77 (s, 3H), 4.04 (q, 2H), 6.88 (br, NH, 7.23 (s, 1H), 7.25 (s, 1H) P-06 —CO.sub.2Et Me Me Et Cl trans 1.15 (t, 3H), 1.18 (t, 3H), 1.59-1.85 (m, 1H), 1.83-2.00 (m, 4H), 2.04 (s, 3H), 2.21-2.59 (m, 3H), 3.30-3.38 (m, 2H), 3.34 (s, 3H), 4.04 (q, 2H), 7.20 (s, 1H), 7.29 (s, 1H) P-07 —COiPr Et Me Et Cl trans 1.04 (d, 6H), 1.18 (t, 3H), 1.20 (t, 3H), 1.62-1.64 (m, 1H), 1.79-2.03 (m, 3H), 2.04 (s, 3H), 2.09-2.26 (m, 1H), 2.47-2.53 (m 2H), 2.59 (q, 2H), 3.33-3.39 (m, 2H), 3.38 (q, 2H), 6.38 (br, NH), 7.20 (s, 1H), 7.26 (s, 1H) P-08 —CO.sub.2Et Me Me OMe Br trans 1.17 (t, 3H), 1.64-1.85 (m, 1H), 1.85-1.88 (m, 3H), 2.05 (s, 3H), 2.24-2.30 (m, 1H), 2.46-2.51 (m, 1H), 3.35 (s, 3H), 3.78 (s, 3H), 4.05 (q, 2H), 6.13 (br, NH), 6.87 (s, 1H), 7.25 (s, 3H) P-09 —CO.sub.2Et Et Me Me Cl trans 1.13 (t, 3H), 1.20 (t, 3H), 1.85 (m, 1H), 1.90 (m, 3H), 2.03 (s, 3H), 2.28 (m, 1H), 2.51 (m, 1H), 3.38 (m, 2H), 3.49 (q, 2H), 4.05 (q, 2H), 7.16 (s, 1H), 7.27 (s, 1H) P-11 —CO.sub.2Et Et Me Me Cl cis 1.17 (t, 3H), 1.28 (t, 3H), 1.67-1.73 (m 1H), 1.79-1.91 (m 2H), 197-2.20 (m, 2H), 2.04 (s, 3H), 2.26 (s, 3H), 2.35-2.44 (m, 1H), 2.50 (m, 1H), 3.39-3.52 (m, 2H), 3.58 (q, 2H), 4.06 (q, 2H), 7.15 (s, 1H), 7.27 (s, 1H) P-12 —COiPr Et Me Et Cl cis 1.21 (t, 3H), 1.30 (t, 3H), 1.70 (m, 1H), 1.83-1.99 (m, 3H), 2.04 (s, 3H), 2.27 (m, 1H). 2.55-2.67 (m, 4H), 3.40-3.60 (m, 4H), 7.19 (s, 1H), 7.25 (s, 1H) P-13 —CO.sub.2Et Me Me OMe Br cis 1.17 (t, 3H), 1.69-1.89 (m, 3H), 1.97-2.16 (m, 2H), 2.04 (s, 3H), 2.37-2.53 (m, 2H), 3.34-3.44 (m, 2H), 3.40 (s, 3H), 3.78 (s, 3H), 4.05 (q, 2H), 6.81 (br, NH), 6.86 (s, 1H), 7.25 (s, 1H) P-14 —COiPr Me Me Et Cl trans 1.15 (t, 3H), 1.59-1.65 (m 1H), 1.83-2.00 (m 3H), 2.03 (s, 3H), 2.20.2.32 (m, 1H), 2.25 (s, 3H), 2.48-2.56 (m, 1H), 3.30-3.39 (m, 2H), 3.34 (s, 3H), 4.06 (q, 2H), 6.64 (br, NH), 7.16 (s, 1H), 7.27 (s, 1H) P-15 —CO.sub.2Et Me Me Et Cl cis 1.13 (t, 3H), 1.19 (t, 3H), 1.67-1.71 (m, 1H), 1.79-1.93 (m, 2H), 2.04 (s, 3H), 2.09-2.20 (m, 2H), 2.36-2.87 (m, 2H), 3.34 (m, 1H), 3.41 (s, 3H), 3.42-3.48 (m, 1H), 4.04 (q, 2H), 7.20 (s, 1H), 7.28 (s, 1H) P-16 —COiPr Me Me Me Cl cis 1.03 (d, 6H), 1.72 (m, 1H), 1.82-2.00 (m, 3H), 2.03 (s, 3H), 2.08-2.25 (m, 1H), 2.27 (s, 3H), 2.39-2.50 (m, 2H), 2.61 (m, 1H), 3.36 (m, 1H), 3.41 (s, 3H), 3.45 (m, 1H), 7.14 (s, 1H), 7.24 (s, 1H) P-17 —COiPr Et Me Me Cl cis 1.03-1.08 (d, 6H), 1.28-1.30 (t, 3H), 1.66-1.73 (m, 1H), 1.78-2.01 (m, 3H), 2.03 (s, 3H), 2.27 (s, 3H), 2.42 (m, 1H), 2.60-2.83 (hept, 1H), 3.39 (m, 2H), 3.54-3.61 (q, 2H), 7.14 (s, 1H), 7.24 (s, 1H) P-18 —CO.sub.2Et Me Me Me Cl trans 1.15 (t, 3H), 1.59-1.65 (m, 1H), 1.80-2.00 (m, 4H), 2.03 (s, 3H), 2.20-2.30 (m, 1H), 2.25 (s, 3H), 2.48-2.56 (m, 1H), 3.30-3.39 (m, 2H), 3.34 (s, 3H), 4.06 (q, 2H), 6.64 (br, Nh), 7.16 (s, 1H), 7.27 (s, 1H) P-19 —CO.sub.2Et Me H OMe Cl trans 1.18 (t, 3H), 1.63-1.84 (m, 1H), 1.88-2.01 (m, 4H), 2.24-2.28 (m, 1H), 2.27- 2.50 (m, 1H), 3.32-3.37 (m, 2H), 3.35 (s, 3H), 3.80 (s, 3H), 4.06 (q, 2H), 6.19 (br, NH), 6.92 (s, 1H), 7.17 (s, 1H) P-20 —CO.sub.2Et Et Me Et Cl cis 1.13 (t, 3H), 1.21 (t, 3H), 1.30 (t, 3H), 1.70 (m, 1H) 1.85-1.92 (m, 2H), 2.04 (s, 3H), 2.13 (m, 1H), 2.20-2.63 (m, 1H), 3.39 (q, 2H), 3.58 (q, 2H), 4.04 (q, 2H), 7.20 (s, 1H), 7.29 (s, 1H) P-21 —CO.sub.2Et Et Me Et Cl trans 1.13 (t, 3H), 1.17 (t, 3H), 1.21 (t, 3H), 1.65 (m, 1H), 1.85-1.99 (m, 3H), 2.04 (s, 3H), 2.28 (m, 1H), 2.50 (m, 1H), 2.53 (q, 2H), 3.41 (q, 2H), 3.51 (q, 2H), 4.06 (q, 2H), 7.2 (s, 1H), 7.29 (s, 1H) P-22 —COiPr Me Me Et Cl cis 1.13-1.18 (d, 6H), 1.64-1.68 (m, 1H), 1.79-2.00 (m, 3 H), 2.04 (s, 3H), 2.21- 2.48 (m, 1H), 2.55-.265 (m, 3H), 3.30-3.39 (m, 2H), 3.34 (s, 3H), 4.04 (q, 2H), 6.63 (br, NH), 7.20 (s, 1H), 7.29 (s, 1H) P-23 —COiPr Et Me OMe Br trans 1.17 (d, 6H), 1.19 (t, 3H), 1.58-1.63 (m 1H), 1.79-2.00 (m, 4H), 2.04 (s, 3H), 2.11-2.23 (m, 1H), 2.46-2.52 (m, 1H), 2.63 (hept, 1H), 3.36-3.39 (m, 2H), 3.47 (q, 2H), 3.87 (s, 3H), 6.38 (br, NH), 6.86 (s, 1H), 7.22 (s, 1H) P-24 —CO.sub.2Et Me Me Me Cl cis 1.12-1.17 (t, 3H), 1.68-1.78 (m, 1H), 1.80-1.87 (m, 2H), 2.03 (s, 3H), 2.16 (m, 2H), 2.28 (s, 3H), 2.34-2.54 (m, 2H), 3.34-3.88 (m, 2H), 3.41 (s, 3H), 4.04 (q, 2H), 7.15 (s, 1H), 7.28 (s, 1H) P-25 —COiPr Et Me OMe Cl trans 1.09 (d, 6H), 1.19 (t, 3H), 1.60-163 (m, 1H), 1.80-2.00 (m, 4H), 2.04 (s, 3H), 2.13-2.27 (m, 1H), 2.42-2.50 (m, 1H), 2.62 (hept, 1H), 3.37 (m, 2H), 3.48 (q, 2H), 3.71-3.82 (m, 1H), 3.78 (s, 3H), 6.13 (br, NH), 6.82 (s, 1H), 7.04 (s, 1H) P-26 —CO.sub.2Et Et Me OMe Cl trans 1.15 (t, 3H), 1.19 (t, 3H), 1.62-1.64 (m 1H), 1.80-2.00 (m, 4H), 2.05 (s, 3H), 2.21-2.29 (m, 1H), 2.30-2.51 (m, 1H), 3.37 (m, 2H), 3.49 (q, 2H), 3.78 (s, 3H), 4.06 (q, 2H), 6.19 (br, NH), 6.83 (s, 1H), 7.07 (s, 1H) P-27 —CO.sub.2Et Et Me OMe Cl trans 1.18 (t, 6H), 1.66-1.84 (m, 1H), 1.92-2.03 (m, 4H), 2.25-2.29 (m 1H), 2.40- 2.52 (m, 1H), 3.36 (m, 2H), 3.48 (q, 2H), 3.80 (s, 3H), 4.08 (q, 2H), 6.11 (br, NH), 6.93 (s, 1H), 7.18 (s, 1H) P-28 —CO.sub.2Et Et Me Me Cl cis 1.2 (t, 3H), 1.4 (m, 2H), 1.6-1.9 (m, 2H), 2.01 (s, 3H), 2.4 (s, 3H), 2.5 (m, 3H), 3.4-3.5 (m, 2H), 3.6 (q, 2H), 4.0 (q, 2H), 6.2 (br, 1H), 7.15 (s, 1H), 7.25 (s, 1H) P-29 —COiPr Et Me Me Cl cis 1.18 (d, 6H), 1.45 (t, 2H), 1.6-1.9 (m, 3H), 2.0 (s, 3H), 2.1 (m, 1H), 2.3 (s, 3H), 2.4 (m, 1H), 2.6 (hept, 1H), 3.4-3.5 (q, 2H), 3.6 (m, 2H), 6.5 (br, 1H), 7.22 (s, 1H), 7.14 (s, 1H) P-30 —CO2Et Me Me Me Br trans 1.18 (t, 3H), 1.6-1.9 (m, 3H), 2.0 (s, 3H), 2.5 (m, 1H), 3.40 (m, 5H), 4.1 (q, 2H), 6.56 (br, 1H), 7.19 (s, 1H), 7.45 (s, 1H) P-31 —CO2Et Me Me Me Br cis 1.2 (t, 3H), 1.58-1.9 (m, 3H), 2.0 (s, 3H), 2.5 (m, 2H), 3.4 (m, 5H), 4.08 (q, 2H), 6.89 (br, 1H), 7.19 (s, 1H), 7.45 (s, 1H) P-32 —COiPr Me Me Me Br cis 1.1 (d, 6H), 1.57-1.9 (m, 3H), 2.01 (s, 3H), 2.2 (s, 3H), 2.5 (m, 1H), 2.7 (hept, 1H), 3.3 (s, 3H), 3.4 (m, 2H), 6.83 (br, 1H), 7.18 (s, 1H), 7.43 (s, 1H) P-33 —COiPr Me Me Me Br trans 1.1 (d, 6H), 1.57-1.9 (m, 3H), 2.01 (s, 3H), 2.2 (s, 3H), 2.5 (m, 1H), 2.6 (hept, 1H), 3.4 (s, 3H), 3.5 (m, 2H), 6.37 (br, 1H), 7.19 (s, 1H), 7.43 (s, 1H) P-34 —CO2Et Et Me Me Br trans 1.1 (t, 3H), 1.2 (t, 3H), 1-6-1.9 (m 3H), 2.0 (s, 3H), 2.1 (m, 1H), 2.3 (s, 3H), 2.5 (m, 2H), 3.4 (m, 2H), 3.6 (q, 2H), 4.1 (q, 2H), 6.24 (br, 1H), 7.20 (s, 1H), 7.46 (s, 1H) P-35 —CO2Et Et Me Me Br cis 1.1 (t, 3H), 1.3 (t, 3H), 1-6-1.9 (m 3H), 2.0 (s, 3H), 2.1 (m, 1H), 2.4 (s, 3H), 2.5 (m, 2H), 3.4 (m, 2H), 3.6 (q, 2H), 4.1 (q, 2H), 7.02 (br, 1H), 7.19 (s, 1H), 7.46 (s, 1H) P-36 —COiPr Et Me Me Br trans 1.1 (d, 6H), 1.3 (t, 3H), 1.6-1.9 (m, 3H), 2.0 (s, 3H), 2.1 (m 1H), 2.4 (s, 3H), 2.5 (m, 1H), 2.6 (hept, 1H), 3.4 (m, 2H), 3.6 (q, 2H), 6.49 (br, 1H), 7.18 (s, 1H), 7.43 (s, 1H) P-37 —COiPr Et Me Me Br cis 1.1 (d, 6H), 1.3 (t, 3H), 1.6-1.9 (m, 4H), 2.0 (s, 3H), 2.1 (m 1H), 2.4 (s, 3H), 2.5 (m, 1H), 2.6 (hept, 1H), 3.4 (m, 2H), 3.6 (q, 2H), 6.98 (br, 1H), 7.18 (s, 1H), 7.43 (s, 1H) P-38 —CO2Et Et Me Et Br cis 1.1 (t, 6H), 1.2 (t, 3H), 1.6-1.9 (m, 4H), 2.1 (s, 3H), 2.4 (m, 1H), 2.5 (m, 3H), 3.4 (q, 2H), 3.6 (q, 2H), 4.1 (q, 2H), 7.0 (br, 1H), 7.2 (s, 1H), 7.46 (s, 1H) P-39 —CO2Et Me Me Et Br cis 1.2 (t, 6H), 1.6-1.9 (m, 3H), 2.0 (s, 3H), 2.4 (m, 1H), 2.5 (m, 3H), 3.3 (m, 2H), 3.4 (s, 3H), 4.1 (q, 2H), 6.8 (br, 1H), 7.22 (s, 1H), 7.46 (s, 1H) P-40 —CO2Et Me Me Et Br trans 1.1 (t, 6H), 1-6-1.9 (m, 3H), 2.1 (s, 3H), 2.2 (m, 1H), 2.6 (m, 3H), 3.3 (q, 2H), 3.3 (s, 3H), 4.1 (q, 2H), 6.1 (br, 1H), 7.2 (s, 1H), 7.4 (s, 1H) P-41 —COiPr Et Me Et Br trans 1.1 (d, 6H), 1.2 (t, 6H), 1.6-1.9 (m, 4H), 2.0 (s, 3H), 2.1 (m, 1H), 2.4 (hept, 1H), 2.6 (m, 3H), 3.4 (q, 2H), 3.5 (q, 2H), 6.25 (br, 1H), 7.15 (s, 1H), 7.45 (s, 1H) P-42 —CO2Et Et Me Et Br trans 1.1 (t, 9H), 1.6-1.9 (m, 4H), 2.1 (s, 3H), 2.4 (m, 1H), 2.5 (m, 3 H), 3.4 (q, 2H), 3.6 (q, 2H), 4.1 (q, 2H), 6.42 (br, 1H), 7.2 (s, 1H), 7.46 (s, 1H) P-43 —COiPr Et Me Et Br cis 1.1 (d, 6H), 1.2 (t, 6H), 1.3 (t, 3H), 1.6-1.9 (m, 3H), 2.0 (s, 3H), 2.2-2.5 (m, 1H), 2.6 (m 2H), 3.4 (q, 2H), 3.6 (q, 2H), 6.8 (br, 1H), 7.15 (s, 1H), 7.44 (s, 1H) P-44 —COiPr Me Me Et Br trans 1.1 (d, 6H), 1.2 (t, 3H), 1.6-1.9 (m, 4H), 2.1 (s, 3H), 2.3 (m, 1H), 2.63 (m, 4H), 3.4 (m, 2H) 3.34 (s, 3H), 6.24 (br, 1H), 7.15 (s, 1H), 7.45 (s, 1H) P-45 —COiPr Me Me Et Br cis 1.1 (d, 6H), 1.2 (t, 3H), 1.4-1.9 (m, 4H), 2.1 (s, 3H), 2.3 (m, 1H), 2.63 (m, 4H), 3.4 (m, 2H) 3.5 (s, 3H), 6.8 (br, 1H), 7.15 (s, 1H), 7.45 (s, 1H) P-46 —COiPr Me Me OMe Me cis 1.0 (d, 6H), 1.6-1.9 (m, 4H), 2.1 (s, 3H), 2.2 (s, 3H), 2.3-2.6 (m, 3H), 3.4 (m, 1H), 3.4 (s, 3H), 3.7 (s, 3H), 6.6 (br, 1H), 6.7 (s, 1H), 6.9 (s, 1H) P-47 —CO2Et Me Me OMe Me trans 1.1 (t, 3H), 1.6-1.9 (m, 4H), 2.0 (s, 3H), 2.2 (s, 3H), 2.3 (m, 1H), 2.6 (m, 1H), 3.4 (q, 2H), 3.4 (s, 3H), 3.7 (s, 3H), 4.0 (q, 2H), 6.39 (br, 1H), 6.75 (s, 1H), 6.89 (s, 1H) P-48 —CO2Et Et Me OMe Me trans 1.1 (t, 3H), 1.2 (t, 3H), 1.5-1.9 (m, 3H), 2.0 (s, 3H), 2.2 (s, 3H), 2.4 (m, 1H), 2.6 (m , 1H), 3.4 (m, 2H), 3.5 (q, 2H), 3.6 (s, 3H), 4.0 (q, 2H), 6.30 (br, 1H), 6.75 (s, 1H), 6.89 (s, 1H) P-49 —CO2Et Et Me OMe Me cis 1.1 (t, 3H), 1.2 (t, 3H), 1.6-1.9 (m, 3H), 2.0 (s, 3H), 2.2 (s, 3H), 2.4-2.6 (m, 2H), 3.4 (m, 2H), 3.5 (q, 2H), 3.6 (s, 3H), 4.0 (q, 2H), 6.74 (br, 1H), 6.81 (s, 1H), 6.89 (s, 1H) P-50 —COiPr Et Me OMe Me trans 1.1 (d, 6H), 1.2 (t, 3H), 1.6-1.9 (m, 3H), 2.0 (s, 3H), 2.2 (s, 3H), 2.4 (m, 1H), 2.5 (hept, 1H), 3.4 (m, 2H), 3.5 (q, 2H), 3.7 (s, 3H), 6.14 (br, 1H), 6.73 (s, 1H), 6.88 (s, 1H) P-51 —CO2Et Me Me F Me cis 1.1 (t, 3H), 1.6-1.7 (m, 3H), 2.0 (s, 3H), 2.1 (m, 1H), 2.2 (s, 3H), 2.4-2.5 (m, 2H), 3.4 (m, 2H), 3.5 (s, 3H), 4.0 (q, 2H), 6.84 (br, 1H), 6.92 (s, 1H), 7.06 (s, 1H) P-52 —CO2Et Me Me F Me trans 1.1 (t, 3H), 1.5-1.9 (m, 4H), 2.0 (s, 3H), 2.1 (m, 1H), 2.2 (s, 3H), 2.4-2.5 (m, 2H), 3.4 (m, 2H), 3.5 (s, 3H), 4.0 (q, 2H), 6.43 (br, 1H), 6.92 (s, 1H), 7.06 (s, 1H) P-53 —CO2Et Et Me F Me cis 1.1 (t, 3H), 1.2 (t, 3H), 1.6-1.9 (m, 4H), 2.0 (s, 3H), 2.2 (s, 3H), 2.4-2.5 (m, 2H), 3.4 (m, 2H), 3.5 (q, 2H), 4.0 (q, 2H), 6.91 (br, 1H), 6.92 (s, 1H), 7.07 (s, 1H) P-54 —CO2Et Et Me F Me trans 1.1 (t, 3H), 1.15 (t, 3H), 1.6 (m, 1H), 1.6-1.9 (m, 3H), 2.0 (s, 3H), 2.3-2.4 (m, 1H), 2.2 (s, 3H), 2.5 (m, 1H), 3.4 (m, 2H), 3.5 (q, 2H), 4.0 (q, 2H), 6.54 (br, 1H), 6.92 (s, 1H), 7.06 (s, 1H) P-55 —CO2Et Me Me OMe Me cis 1.1 (t, 3H), 1.6-1.9 (m 3H), 2.0 (s, 3H), 2.4-2.6 (m 2H), 3.35 (m, 2H), 3.4 (s, 3H), 3.7 (s, 3H), 4.0 (q, 2H), 6.71 (br, 1H), 6.77 (s, 1H), 6.89 (s, 1H) P-56 —COiPr Et Me Me F trans 1.1 (d, 6H), 1.3 (t, 3H), 1.6-1.9 (m, 5H), 2.0 (s, 3H), 2.4 (m, 1H), 2.5 (hept, 1H), 3.4 (m, 2H), 3.5 (q, 2H), 6.18 (br, 1H), 6.98 (s, 1H), 7.04 (s, 1H) P-57 —COiPr Me Me Me F trans 1.1 (d, 6H), 1.6-2 (m, 5H), 2.0 (s, 3H), 2.2 (s, 3H), 2.4 (m, 1H), 2.5 (hept, 1H), 3.4 (m, 2H), 3.4 (s, 3H), 6.33 (br, 1H), 6.90 (s, 1H), 7.05 (s, 1H) P-58 —COiPr Me Me Me F cis 1.1 (d, 6H), 1.6-1.9 (m, 3H), 2.0 (s, 3H), 2.2 (s, 3H), 2.4 (m, 2H), 2.5 (hept, 1H), 3.4 (m, 2H), 3.5 (s, 3H), 6.86 (br, 1H), 6.90 (s, 1H), 7.05 (s, 1H) P-59 —COiPr Et Me Me F cis 1.1 (d, 6H), 1.3 (t, 3H), 1.6-1.9 (m, 4H), 2.0 (s, 3H), 2.4 (m, 2H), 2.5 (hept, 1H), 3.4 (m, 2H), 3.5 (q, 2H), 6.87 (br, 1H), 6.90 (s, 1H), 7.04 (s, 1H) P-60 —COiPr Et Me OMe Me cis 1.1 (d 6H), 1.6-1.9 (m, 3H), 2.0 (s, 3H), 2.2 (s, 3H), 2.3-2.6 (m, 2H), 3.4 (m, 2H), 3.6 (q, 2H), 3.7 (s, 3H), 6.73 (br, 1H), 6.95 (s, 1H), 7.27 (s, 1H) P-61 —CO2Et Et Me F OMe trans 1.1 (t, 3H), 1.2 (t, 3H), 1.6-1.9 (m, 4H), 2.0 (s, 3H), 2.2 (m, 1H), 2.5 (m, 1H), 3.4 (m, 2H), 3.5 (q, 2H), 3.7 (s, 3H), 4.0 (q, 2H), 6.10 (br, 1H), 6.71 (s, 1H), 6.79 (s, 1H) P-62 —CO2Et Me Me F OMe trans 1.2 (t, 3H), 1.6-1.9 (m, 4H), 2.0 (s, 3H), 2.4-2.5 (m, 2H), 3.4 (m, 2H), 3.4 (s, 3H), 3.6 (s, 3H), 4.0 (q, 2H), 6.07 (br, 1H), 6.72 (s, 1H), 6.79 (s, 1H) P-63 —CO2Et Me Me F OMe cis 1.2 (t, 3H), 1.6-1.9 (m, 3H), 2.0 (s, 3H), 2.1 (m, 1H), 2.4-2.5 (m, 2H), 3.4 (m, 2H), 3.4 (s, 3H), 3.6 (s, 3H), 4.0 (q, 2H), 6.70 (br, 1H), 6.72 (s, 1H), 6.73 (s, 1H) P-64 —COiPr Et Me OMe F trans 1.1 (d, &h), 1.2 (t, 3H), 1.6-1.9 (m, 4H), 2.0 (s, 3H), 2.2 (m, 1H), 2.4 (m 1H), 2.6 (hept, 1H), 3.4 (s, 3H), 3.5 (q, 2H), 3.7 (s, 3H), 6.03 (br, 1H), 6.72 (s, 1H), 6.75 (s, 1H) P-65 —COiPr Me Me OMe F cis 1.1 (d, 6H), 1.6-1.9 (m, 3H), 2.0 (s, 3H), 2.4 (m, 1H), 2.45 (hept, 1H), 2.5 (m, 1H), 3.4 (m 2H), 3.4 (s, 3H), 3.7 (s, 3H), 6.71 (br, 1H), 6.72 (s, 1H), 6.73 (s, 1H) P-66 —COiPr Me Me OMe F trans 1.1 (d, 6H), 1.6-1.9 (m, 3H), 2.0 (s, 3H), 2.1 (m, 1H), 2.4 (m, 1H), 2.5 (hept, 1H), 3.4 (s, 3H), 3.7 (s, 3H), 6.16 (br, 1H), 6.72 (s, 1H), 6.75 (s, 1H) P-67 —COiPr Et Me OMe F cis 1.1 (d, 6H), 1.2 (t, 3H), 1.6-1.9 (m, 4H), 2.0 (s, 3H), 2.3-2.4 (m, 1H), 2.45 (m, 1H), 2.6 (hept, 1H), 3.4 (m, 2H), 3.5 (q, 2H), 3.8 (s, 3H), 6.70 (br, 1H), 6.73 (s, 1H), 6.86 (s, 1H) P-68 —CO2Et allyl Me OMe Me cis 1.1 (t, 3H), 1.6-1.9 (m, 3H), 2.0 (s, 3H), 2.1 (m, 1H), 2.2 (s, 3H), 2.4-2.5 (m, 2H), 3.4 (m, 2H), 3.7 (s, 3H), 4.0 (m, 4H), 5.3 (dt, 2H), 6.0 (m, 1H), 6.62 (br, 1H), 6.74 (s, 1H), 7.00 (s, 1H) P-69 —CO2Et Et Me F OMe cis 1.1 (t, 3H), 1.2 (t, 3H), 1.5-2.1 (m, 4H), 2.0 (s, 3H), 3.4 (m, 2H), 3.5 (q, 2H), 3.7 (s, 3H), 4.1 (q, 2H), 6.70 (br, 1H), 6.72 (s, 1H), 6.88 (s, 1H) P-71 —CO2Et allyl Me Cl Me cis 1.1 (t, 3H), 1.6-1.9 (m, 3H), 2.0 (s, 3H), 2.1 (m, 1H), 2.2 (s, 3H), 2.4-2.5 (m, 2H), 3.4 (m, 2H), 4.0 (m, 4H), 5.32 (dt, 2H), 5.95 (dq, 1H), 6.79 (br, 1H), 6.85 (s, 1H), 7.15 (s, 1H) P-72 —CO2Et allyl Me Cl Me trans 1.1 (t, 3H), 1.6-1.9 (m, 4H), 2.0 (s, 3H), 2.2 (s, 3H), 2.4-2.5 (m, 2H), 3.4 (m, 2H), 4.0 (q, 2H), 4.1 (dt, 2H), 5.32 (dq, 2H), 5.95 (m, 1H), 6.35 (br, 1H), 7.16 (s, 1H), 7.26 (s, 1H) P-75 —CO2Et 2- Me Cl Me cis 1.1 (t, 3H), 1.6-1.9 (m, 3H), 2.0 (s, 3H), 2.2 (m, 1H), 2.3 (s, 3H), 2.4 (m, methoxy- 2H), 3.4 (s, 3H), 3.5 (m, 2H), 3.6 (m, 4H), 4.0 (q, 2H), 7.14 (br, 1H), 7.28 (s, ethyl 1H), 7.29 (s, 1H) P-76 —CO2Et 2- Me Cl Me trans 1.1 (t, 3H), 1.6-1.9 (m, 4H), 2.0 (s, 3H), 2.2 (m, 1H), 2.3 (s, 3H), 2.4 (m, methoxy- 1H), 3.4 (s, 3H), 3.5 (m, 2H), 3.6 (m, 4H), 4.0 (q, 2H), 6.35 (br, 1H), 7.16 (s, ethyl 1H), 7.26 (s, 1H) P-77 —CO2Et allyl Me OMe F trans 1.1 (t, 3H), 1.6-1.9 (m, 4H), 1.9-2.1 (m, 2H), 2.0 (s, 3H), 2.4-2.5 (m, 2H), 3.4 (m, 2H), 3.7 (s, 3H), 4.0 (m, 2H), 4.1 (m, 2H), 5.17 (qd, 1H), 5.29 (qd, 1H), 5.94 (m, 1H), 6.15 (br, 1H), 6.72 (s, 1H), 6.77 (s, 1H) P-78 —CO2Et allyl Me OMe F cis 1.1 (t, 3H), 1.6-1.8 (m, 3H), 1.9-2.1 (m, 1H), 2.0 (s, 3H), 2.4-2.5 (m, 2H), 3.4 (m, 2H), 3.7 (s, 3H), 4.0 (m, 4H). 5.22 (qd, 1H), 5.31 (qd, 1H), 5.94 (m, 1H), 6.68 (br, 1H), 6.72 (s, 1H), 6.77 (s, 1H) P-79 —CO2Et 2- Me OMe Me cis 1.1 (t, 3H), 1.6-1.1.9 (m, 4H), 2.0 (s, 3H), 2.2 (s, 3H), 2.4-2.5 (m, 2H), 3.4 (s, methoxy- 3H), 3.5 (m, 2H), 3.6 (m, 4H), 3.7 (s, 3H), 4.0 (q, 2H), 6.73 (br, 1H), 6.88 (s, ethyl 1H), 7.13 (s, 1H) P-80 —CO2Et 2- Me OMe Me trans 1.1 (t, 3H), 1.6-1.1.9 (m, 5H), 2.0 (s, 3H), 2.2 (s, 3H), 2.4 (m, 1H), 2.5 (m, methoxy- 1H), 3.4 (s, 3H), 3.5 (m, 2H), 3.6 (m, 2H), 3.65 (m, 1H), 3.7 (s, 3H), 4.0 (q, ethyl 2H), 5.96 (br, 1H), 6.75 (s, 1H), 6.89 (s, 1H) P-81 —CO2Et propyl Me Me OMe trans 0.8 (t, 3H), 1.2 (t, 3H), 1.6-1.9 (m, 4H), 2.0 (s, 3H), 2.2 (s, 3H), 2.3 (m, 1H), 2.5 (m, 1H), 3.4 (m, 4H), 3.7 (s, 3H), 4.0 (q, 2H), 6.0 (br, 1H), 6.75 (s, 1H), 6.89 (s, 1H) P-82 —CO2Et propyl Me F OMe cis 0.9 (t, 3H), 1.2 (t, 3H), 1.6 (m, 3H), 1.7 (m, 2H), 2.0 (s, 3H), 2.1 (m, 1H), 2.5 (m, 2H), 3.4 (m, 4H), 3.80 (s, 3H), 4.1 (q, 2H), 6.69 (br, 1H), 6.72 (s, 1H), 6.87 (s, 1H) P-83 —CO2Et propyl Me Me OMe cis 0.9 (t, 3H), 1.1 (t, 3H), 1.7 (m, 3H), 1.8 (m, 1H), 2.0 (s, 3H), 2.1 (m, 1H), 2.2 (s, 3H), 2.5 (m, 2H), 3.4 (m, 4H), 3.8 (s, 3H), 4.0 (q, 2H), 6.74 (s, 1H), 6.76 (s, 1H), 6.89 (s, 1H) P-84 —CO2Et propyl Me F OMe trans 0.9 (t, 3H), 1.2 (t, 3H), 1.6-1.9 (m, 4H), 2.0 (s, 3H), 2.3 (m, 1H), 2.5 (m, 1H), 3.4 (m, 4H), 3.80 (s, 3H), 4.1 (q, 2H), 6.0 (br, 1H), 6.72 (s, 1H), 6.78 (s, 1H) P-85 —CO2Et allyl Me Me Br cis 1.1 (t, 3H), 1.6-1.9 (m, 4H), 2.0 (s, 3H), 2.1 (s. 3H), 2.4-2.5 (m, 2H), 3.5 (m, 2H), 4.0 (m, 4H), 5.23 (qd, 1H), 5.32 (qd, 1H), 5.93 (m, 1H), 6.82 (s, 1H), 7.19 (s, 1H), 7.45 (s, 1H) P-86 —CO2Et propyl Me Cl Me trans 0.9 (t, 3H), 1.1 (t, 3H), 1.6 (m, 4H), 2.0 (s, 3H), 2.3 (s, 3H), 2.4 (m, 2H), 3.4 (m, 4H), 4.0 (q, 2H), 6.41 (br, 1H), 7.16 (s, 1H), 7.27 (s, 1H) P-87 —CO2Et propyl Me Cl Me cis 0.9 (t, 3H), 1.2 (t, 3H), 1.7 (m, 3H), 1.9 (m, 2H), 2.0 (s, 3H), 2.2 (s, 3H), 2.5 (m, 2H), 3.5 (m, 4H), 4.0 (q, 2H), 6.92 (br, 1H), 6.99 (s, 1H), 7.15 (s, 1H) P-88 —CO2Et allyl Me Me Br trans 1.2 (t, 3H), 1.6-1.9 (m, 4H), 2.0 (s, 3H), 2.1 (s. 3H), 2.4-2.5 (m, 2H), 3.5 (m, 2H), 4.0 (m, 2H), 4.1 (q, 2H), 5.23 (qd, 1H), 5.32 (qd, 1H), 5.93 (m, 1H), 6.00 (s, 1H), 7.19 (s, 1H), 7.45 (s, 1H) P-89 —CO2Et Et Me Br OEt trans 1.1 (t, 3H), 1.2 (t, 3H), 1.3 (t, 3H), 1.6-1.9 (m, 4H), 2.0 (s, 3H), 2.4 (m, 1H), 2.5 (m, 1H), 3.4 (m, 2H), 3.5 (q, 2H), 3.9 (q, 2H), 4.1 (q, 2H), 6.0 (br, 1H), 6.82 (s, 1H), 7.24 (s, 1H) P-90 —CO2Et Me Me Br OEt cis 1.4 (t, 6H), 1.6-1.9 (m, 4H), 2.0 (s, 3H), 2.2 (m, 1H), 2.5 (m, 1H), 3.4 (q, 2H), 3.5 (s, 3H), 4.0 (q, 2H), 6.82 (br, 1H), 7.22 (s, 1H), 7.26 (s, 1H) P-94 —CO2Et Me Me Br OEt trans 1.2 (t, 3H), 1.3 (t, 3H), 1.6-1.9 (m, 4H), 2.0 (s, 3H), 2.3 (m, 1H), 2.5 (m, 1H), 3.4 (m, 2H), 3.4 (s, 3H), 4.0 (q, 2H), 4.1 (q, 2H), 5.92 (br, 1H), 6.82 (s, 1H), 7.26 (s, 1H) P-95 —CO2Et Et Me Br OEt cis 1.1 (t, 3H), 1.2 (t, 3H), 1.3 (t, 3H), 1.6-1.9 (m, 3H), 2.0 (s, 3H), 2.1 (m, 1H), 2.5 (m, 2H), 3.4 (m, 2H), 3.5 (m, 2H), 3.9 (q, 2H), 4.1 (q, 2H), 6.80 (br, 1H), 6.82 (s, 1H), 6.83 (s, 1H) P-97 —CO2Et Me Me Cl OMe cis 1.2 (t, 3H), 1.6-1.9 (m, 3H), 2.0 (s, 3H), 2.1 (m, 1H), 2.5 (m, 2H), 3.4 (m, 1H), 3.5 (s, 3H), 3.7 (s, 3H), 4.0 (q, 2H), 6.73 (br, 1H), 6.84 (s, 1H), 7.97 (s, 1H) P-98 —CO2Et Me Me Cl OMe trans 1.2 (t, 3H), 1.6-1.9 (m, 4H), 2.0 (s, 3H), 2.4-2.5 (m, 2H), 3.4 (m, 1H), 3.5 (s, 3H), 3.7 (s, 3H), 4.0 (q, 2H), 6.16 (br, 1H), 6.84 (s, 1H), 7.07 (s, 1H) P-99 —CO2Et prop-2- Me Cl Me trans 1.1 (t, 3H), 1.6-1.9 (m, 4H), 2.0 (s, 3H), 2.2 (s, 3H), 2.3 (m, 1H), 2.4-2.5 (m, yn-1-yl 2H), 3.5 (m, 2H), 4.0 (q, 2H), 4.1 (s, 3H), 6.19 (br, 1H), 7.16 (s, 1H), 7.26 (s, 1H) P- —CO2Et prop-2- Me Cl Me cis 1.1 (t, 3H), 1.7-1.9 (m, 3H), 2.0 (s, 3H), 2.1 (m, 1H), 2.2 (s, 3H), 2.4-2.5 (m, 100 yn-1-yl 2H), 3.5 (m, 2H), 4.0 (q, 2H), 4.2 (m, 2H), 6.63 (s, 1H), 6.66 (s, 1H), 7.15 (s, 1H) P- —CO2Et prop-2- Me OMe Me cis 1.1 (t, 3H), 1.6-1.9 (m, 3H), 2.0 (s, 3H), 2.1 (m, 1H), 2.2 (s, 3H), 2.4-2.5 (m, 101 yn-1-yl 2H), 3.5 (m, 2H), 3.7 (s, 3H), 4.0 (m, 2H), 4.2 (m, 2H), 6.54 (br, 1H), 6.75 (s, 1H), 6.89 (s, 1H) P- —CO2Et prop-2- Me OMe F trans 1.1 (t, 3H), 1.6-1.9 (m, 4H), 2.0 (s, 3H), 2.3 (m, 1H), 2.4-2.5 (m, 2H), 3.5 (m, 102 yn-1-yl 2H), 3.7 (s, 3H), 4.0 (q, 2H), 4.1 (s, 1H), 5.91 (br, 1H), 6.76 (s, 1H), 6.78 (s, 1H) P- —CO2Et prop-2- Me OMe Me trans 1.1 (t, 3H), 1.6-1.9 (m, 4H), 2.0 (s, 3H), 2.2 (s, 3H), 2.3 (m, 1H), 2.4-2.5 (m, 103 yn-1-yl 2H), 3.5 (m, 2H), 3.7 (s, 3H), 4.0 (q, 2H), 4.1 (s, 1H), 6.0 (br, 1H), 6.75 (s, 1H), 6.89 (s, 1H) P- —CO2Et prop-2- Me OMe F cis 1.1 (t, 3H), 1.6-1.9 (m, 3H), 2.0 (s, 3H), 2.2 (s, 3H), 2.3 (m, 1H), 2.4-2.5 (m, 104 yn-1-yl 2H), 3.5 (m, 2H), 3.7 (s, 3H), 4.0 (q, 2H), 4.1 (s, 1H), 6.7 (br, 1H), 6.72 (s, 1H), 6.74 (s, 1H) P- —CO2Et allyl Me Me F cis 1.1 (t, 3H), 1.6-1.9 (m, 3H), 2.0 (s, 3H), 2.1 (m, 1H), 2.2 (s, 3H), 2.4-2.5 (m, 105 2H), 3.5 (m, 2H), 4.0 (m, 4H), 5.23 (qd, 1H), 5.94 (qd, 1H), 6.00 (m, 1H), 6.77 (br, 1H), 6.91 (s, 1H), 7.05 (s, 1H)

[0234] Preparation examples for starting materials:

Example A.6 Methyl 1-[[2-(2-bromo-6-methoxy-4-prop-1-ynylphenyl)acetyl]amino]-3-(methoxymethyl)cyclopentanecarboxylate

[0235] ##STR00033##

[0236] 0.90 g (3.17 mmol) of [2-bromo-6-methoxy-4-(prop-1-yn-1-yl)phenyl]acetic acid was dissolved in 3.33 ml of dichloromethane and 2 drops of dimethylformamide were added. At room temperature, 0.55 ml (6.35 mmol) of oxalyl chloride was slowly added dropwise and the mixture was then heated at reflux until the evolution of gas had ceased and concentrated. In a separate reaction, the acid chloride dissolved in dichloromethane was added dropwise to an initial charge of 0.77 g (3.17 mmol) of [1-methoxycarbonyl-3-(methoxymethyl)cyclopentyl]ammonium chloride and 1.72 ml (12.7 mmol) of triethylamine in 3.3 ml of dichloromethane. Stirring at room temperature was continued for 1 h.

[0237] The mixture was washed with water, the phases were separated and the organic phase was dried over sodium sulfate. After concentrating, the residue was purified by chromatography.

[0238] This gave 1 g of a light-colored oil (76% yield).

[0239] Analogously to this example and also according to the general details relating to the preparation, the following compounds are obtained:

TABLE-US-00003 Example No. Structure .sup.1H NMR (400 MHz, CDCl.sub.3) A1 [00034] embedded image 1.55-1.61 (m, 1H), 1.68-1.74 (m, 1H), 1.81-1.89 (m, 1H), 2.04-2.22 (m, 3H), 2.35 (m, 1H), 3.10 (s, 1H), 3.22 (m, 2H), 3.25 (s, 3H), 3.69 (s, 3H), 3.73 (s, 3H), 3.85 (s, 3H), 6.49 (br, NH), 6.91 (s, 1H), 7.19 (s, 1H) A2 [00035] 1.17 (t, 3H), 1.48-1.51 (m, 1H), 1.79-1.93 (m, 3H), 2.05 (s, 3H), 2.18-2.22 (m, 2H), 2.34 (s, 3H), 3.34 (q, 2H), 3.46 (q, 2H), 3.67 (s, 3H), 3.73 (s, 2H), 5.67 (br, NH), 7.16 (s, 1H), 7.31 (s, 1H) A3 [00036] embedded image 1.15 (t, 3H), 1.23 (t, 3H), 1.50 (m, 1H), 1.85-1.93 (m 3H), 2.05 (s, 3H), 2.18-2.33 (m, 2H), 2.67 (q, 2H), 3.33 (m, 2H), 3.45 (q, 2H), 3.67 (s, 3H), 3.74 (s, 2H), 5.85 (br, NH), 7.19 (s, 1H), 7.32 (s, 1H) A4 [00037] 1.21 (t, 3H), 1.80 (m, 1H), 1.88-2.04 (m, 2H), 2.05 (s, 3H), 2.16-2.20 (m, 2H), 2.69 (m, 2H), 3.26-3.34 (m, 1H), 3.31 (s, 3H), 3.67 (s, 3H), 3.74 (s, 2H), 5.66 (br, NH), 7.19 (s, 1H), 7.32 (s, 1H) A5 [00038] embedded image 1.52-1.88 (m, 3H), 2.05 (s, 3H), 2.17 (m, 2H), 2.35- 2.41(m, 1H), 3.32 (s, 3H), 3.33 (m, 1H), 3.69 (s, 3H), 3.74 (s, 2H), 3.82 (s, 3H), 6.41 (br, NH), 6.86 (s, 1H), 7.26 (s, 1H) A6 [00039] 1.21 (t, 3H), 1.59-1.73 (m, 2H), 1.75 (m, 1H), 2.04 (s, 3H), 2.18-2.45 (m, 3H), 3.33 (m, 2H), 3.48 (q, 2H), 3.68 (s, 3H), 3.82 (s, 2H), 6.56 (br, NH), 6.85 (s, 1H), 7.25 (s, 1H) A7 [00040] embedded image 1.17 (t, 3H), 1.49-1.61 (m, 1H), 1.82-1.97 (m, 3H), 2.04-2.12 (m, 1H), 2.13-2.20 (m, 1H), 2.20-2.41 (m, 1H), 3.33 (q, 2H), 3.46 (q, 2H), 3.68 (s, 3H), 3.73 (s, 2H), 3.86 (s, 3H), 5.86 (br, NH), 6.92 (s, 1H), 7.19 (s, 1H)

2-Fluoro-6-methyl-4-nitroaniline

[0240] ##STR00041##

[0241] To a solution of dimethyl ether (100 ml) and water (60 ml) were added 150 mg (0.64 mmol) of 2-bromo-6-fluoro-4-nitroaniline (CAS number: 455-58-3), 200 mg (1.91 mmol) of sodium carbonate and trimethylboroxine (240 mg, 0.95 mmol) and Pd(dppd)Cl.sub.2 (18.6 mg, 0.02 mmol) under argon, and the mixture was heated at 90° C. for 16 h. The mixture was concentrated to dryness and the residue was dissolved in water and extracted with dichloromethane. The extract was dried with sodium sulfate, concentrated and chromatographed. This gave 188 mg (55%).

[0242] .sup.1H NMR (400 MHz, δ in ppm, CDCl.sub.3)

[0243] δ=2.26 (s, 3H), 4.36 (br, NH2), 7.81 (s, 1H), 7.86 (s, 1H)

1-Fluoro-3-methyl-5-nitro-2-(2,2,2-trichloroethyl)benzene

[0244] ##STR00042##

[0245] 132 mg (1.28 mmol) of tert-butyl nitrite and 144 mg (1.06 mmol) of copper(II) chloride were suspended in 7.8 ml of acetonitrile and cooled to 0° C. Then 983 mg (10.1 mmol) of vinylidene chloride was slowly added dropwise and the mixture was allowed to warm to room temperature. Subsequently, 123 mg (0.72 mmol) of 2-fluoro-6-methyl-4-nitroaniline, dissolved in 10 ml of acetonitrile and 25 ml of acetone, was slowly added dropwise. Stirring at room temperature was continued until the evolution of gas had ceased.

[0246] While cooling with ice, the mixture was slowly added to 2 ml of 10% aqueous hydrochloric acid and extracted with ethyl acetate, and the extract was dried with magnesium sulfate and concentrated. This gave 3.636 g of a crude product which still contained copper salts and was used directly for the next reaction.

[0247] .sup.1H NMR (400 MHz, δ in ppm, CDCl.sub.3)

[0248] δ=2.66 (s, 3H), 1.96 (s, 2H), 7.83 (s, 1H), 7.96 (s, 1H)

Methyl 2-(2-fluoro-6-methyl-4-nitrophenyl)acetate

[0249] ##STR00043##

[0250] 160 mg (0.55 mmol) of 1-fluoro-3-methyl-5-nitro-2-(2,2,2-trichloroethyl)benzene was dissolved in 10 ml of methanol, and 121 mg (2.23 mmol) of 30% methanolic sodium methoxide solution was added slowly, resulting in evolution of heat. The mixture was then heated at reflux for 12 h. 1.1 ml of concentrated sulfuric acid was added cautiously, resulting in evolution of heat. The mixture was heated under reflux for 1 h. The mixture was concentrated to dryness and the residue was dissolved in water and extracted with dichloromethane. The extract was dried with sodium sulfate, concentrated and chromatographed. This gave 110 mg of a yellow oil (75% yield).

[0251] .sup.1H NMR (400 MHz, δ in ppm, CDCl.sub.3)

[0252] δ=2.42 (s, 3H), 3.72 (s, 3H), 3.78 (s, 2H), 7.78 (s, 1H), 7.91 (s, 1H)

Methyl 2-(4-amino-2-fluoro-6-methylphenyl)acetate

[0253] ##STR00044##

[0254] 1.40 g (6.16 mmol) of methyl (2-fluoro-6-methyl-4-nitrophenyl)acetate was dissolved in 11 ml of tetrahydrofuran, and a solution of 2.040 g (38.1 mmol) of ammonium chloride in 5.3 ml of water and 1.37 g (2.46 mmol) of iron powder were added. The mixture was stirred at room temperature for 30 min. The mixture was filtered, the filtrate was diluted with water and extracted with ethyl acetate, adjusting the pH to greater than 7. The extract was dried with sodium sulfate and concentrated. 1.17 g a brown substance was obtained (90% yield).

Methyl 2-(2-fluoro-4-Iodo-6-methylphenyl)acetate

[0255] ##STR00045##

[0256] A suspension of 1.40 g (6.16 mmol) of methyl (4-amino-2-fluoro-6-methylphenyl)acetate and 3 ml (3.76 mol) of HCl in 30 ml of water was cooled to −5-0° C., and a solution of 0.4 g (6.03 mmol) of sodium nitrite and 0.8 g (11.08 mmol) of potassium iodide in 1.8 ml of water was added gradually. After 10 min, the mixture was warmed to room temperature and stirred at 20° C. for a further 30 min. 15 ml of water was added, the pH was adjusted to pH 8 with saturated sodium hydrogencarbonate solution, and then saturated sodium thiosulfate solution was added. After extraction with ethyl acetate, drying (sodium sulfate) and distillative removal of the solvent, the residue was purified by chromatography on silica gel (ethyl acetate/hexane). This gave 1.35 g (75%) of the iodine compound as a white solid.

[0257] .sup.1H NMR (400 MHz, δ in ppm, CDCl.sub.3)

[0258] δ=2.26 (s, 3H), 3.64 (s, 2H), 3.70 (s, 3H), 7.29 (s, 1H), 7.35 (s, 1H)

Example B.8

Methyl 2-(2-fluoro-6-methyl-4-prop-1-ynylphenyl)acetate

[0259] ##STR00046##

[0260] To a solution of 0.102 g (0.75 mmol) of zinc chloride and 0.032 g (0.75 mmol) of lithium chloride in 7 ml of dry tetrahydrofuran under nitrogen at 0° C. was added dropwise, while stirring, 1.5 ml (0.75 mmol) of a 0.5 M solution of 1-propylmagnesium bromide in tetrahydrofuran. The solution was warmed to room temperature while stirring within 1.5 h (solution 1). 2.8 mg (0.01 mmol) of palladium(II) acetate and 10.6 mg (0.02 mmol) of 1,4-bis(diphenylphosphino)butane in 3 ml of dry tetrahydrofuran were stirred under a nitrogen atmosphere at room temperature for 30 min (solution 2).

[0261] 0.14 g (0.5 mmol) of methyl (2-fluoro-6-methyl-4-iodophenyl)acetate was dissolved in 2 ml of dry tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred at room temperature for 30 min (solution 3).

[0262] Solution 2 and then solution 3 were each added dropwise at room temperature to solution 1 while stirring and, after the addition had ended, the mixture was stirred at 60° C. for 3.5 h.

[0263] After cooling to room temperature, water and saturated ammonium chloride solution were added, the mixture was extracted with ethyl acetate, the organic phase was dried (sodium sulfate), and the solvent was distilled off. Chromatography on silica gel (ethyl acetate/hexane) gave 75 mg of the desired compound (65% yield).

[0264] .sup.1H NMR (400 MHz, δ in ppm, CDCl.sub.3):

[0265] δ=2.04 (s, 3H), 2.23 (s, 3H), 3.62 (s, 3H), 3.71 (s, 2H), 7.04 (s, 1H), 7.10 (s, 1H)

[0266] The following precursors were prepared analogously:

##STR00047##

TABLE-US-00004 TABLE 3 Compounds of the general formula (X) Example No. R.sup.3 X Y .sup.1H NMR (400 MHz, δ in ppm) B.1 Me Cl Me (d.sub.6-DMSO): δ = 2.02 and 2.26 (each s, each 3H), 3.72 (s, 2H), 7.11 and 7.19 (each s, each 1H) B.2 Me Cl Et (CDCl.sub.3): δ = 1.21 (t, 3H), 2.10 (s, 3H), 2.67 (q, 2H), 3.92 (s, 2H), 7.06 and 7.34 (each s, each 1H) B.3 Me Br Me (d.sub.6-DMSO): δ = 2.05 and 2.28 (each s, each 3H), 3.78 (s, 2H), 7.26 and 7.45 (each s, each 1H) B.4 Me Br OMe (CDCl.sub.3): δ = 2.05 (s, 3H), 3.80 (s, 3H), 3.90 (s, 2H), 6.80 (s, 1H), 7.25 (s, 1H) B.5 Me Br OEt (d.sub.6-DMSO): δ = 1.30 (t, 3H), 2.05 (s, 3H), 3.65 (s, 2H), 4.05 (q, 2H), 7.00 (s, 1H), 7.20 (s, 1H) B.6 H Br OMe (d.sub.6-DMSO): δ = 3.70 (s, 2H), 3.80 (s, 3H), 4.30 (s, 1H), 7.10 (s, 1H), 7.30 (s, 1H) B.7 Me Cl OMe (CDCl.sub.3): δ = 2.04 (s, 3H), 3.80 (s, 3H), 3.85 (s, 2H), 6.80 (s, 1H), 7.06 (s, 1H) B.8 Me F Me (CDCl.sub.3): δ = 2.04 (s, 3H), 2.27 (s, 3H) 3.71 (s, 2H), 6.93 (s, 1H), 7.02 (s, 1H)

B. Formulation Examples

[0267] 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 inert substance and comminuting the mixture in an impact mill.
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 inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurate as wetting agent and dispersant and grinding in a pinned-disc mill.
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 e.g. about 255 to more than 277° C.) and grinding to a fineness of below 5 microns in an attrition ball mill.
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 solvent and 10 parts by weight of oxyethylated nonylphenol as emulsifier.
e) Water-dispersible granules are obtained by mixing
75 parts by weight of a compound of the formula (I) and/or salts thereof,
10 parts by weight of calcium lignosulfonate,
5 parts by weight of sodium laurylsulfate,
3 parts by weight of polyvinyl alcohol and
7 parts by weight of kaolin,
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.
f) Water-dispersible granules are also obtained by homogenizing and precomminuting, in a colloid mill,
25 parts by weight of a compound of the formula (I) and/or salts thereof,
5 parts by weight of sodium 2,2′-dinaphthylmethane-6,6′-disulfonate,
2 parts by weight of sodium oleoylmethyltaurate,
1 part by weight of polyvinyl alcohol,
17 parts by weight of calcium carbonate and
50 parts by weight of water,
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

[0268] 1. Pre-Emergence Herbicidal Effect and Crop Plant Compatibility

[0269] 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 as aqueous suspension or emulsion at a water application rate equating to 600 to 800 L/ha with addition of 0.2% wetting agent.

[0270] 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).

[0271] Undesired Plants/Weeds:

TABLE-US-00005 ALOMY: Alopecurus myosuroides SETVI: Setaria viridis AMARE: Amaranthus retroflexus AVEFA: Avena fatua CYPES: Cyperus esculentus ECHCG: Echinochloa crus-galli LOLRI: Lolium rigidum STEME: Stellaria media VERPE: Veronica persica VIOTR: Viola tricolor POLCO: Polygonum convolvulus ABUTH: Abutylon threophrasti HORMU: Hordeum murinum DIGSA: Digitaria sanguinalis

[0272] 1. Pre-Emergence Effectiveness

[0273] As the results from Tables 3 and 4 show, compounds of the invention have a good herbicidal pre-emergence effectiveness against a broad spectrum of weed grasses and weeds.

TABLE-US-00006 TABLE 4 Pre-emergence action at 320 g/ha against ALOMY in % Example Dosage number [g/ha] ALOMY I-02 320 100 I-05 320 100 I-10 320 100 I-11 320 100 I-17 320 100 I-18 320 100 I-19 320 100 I-20 320 100 I-21 320 100 I-30 320 100 I-31 320 100 I-32 320 100 I-33 320 100 I-35 320 100 I-36 320 100 I-37 320 80 I-40 320 100 I-43 320 100 I-44 320 100 I-45 320 80 I-46 320 100 I-47 320 100 I-48 320 100 I-49 320 100 I-50 320 100 I-51 320 100 I-52 320 100 I-54 320 100 I-55 320 100 I-56 320 80 I-57 320 100 I-58 320 100 I-59 320 100 I-61 320 100 I-62 320 100 I-63 320 100 I-64 320 100 I-66 320 100 I-67 320 100 I-68 320 100 I-69 320 100 I-70 320 100 I-71 320 100 I-72 320 100 I-73 320 100 I-74 320 100 I-75 320 90 I-76 320 100 I-77 320 100 I-78 320 100 I-79 320 100 P-01 320 100 P-04 320 100 P-05 320 100 P-08 320 100 P-100 320 100 P-101 320 100 P-102 320 100 P-103 320 100 P-104 320 100 P-13 320 100 P-23 320 100 P-28 320 100 P-29 320 100 P-30 320 100 P-31 320 100 P-32 320 100 P-33 320 100 P-34 320 100 P-35 320 100 P-36 320 100 P-37 320 100 P-46 320 100 P-47 320 100 P-48 320 100 P-49 320 100 P-50 320 100 P-51 320 100 P-52 320 100 P-53 320 100 P-54 320 100 P-55 320 100 P-56 320 100 P-57 320 100 P-58 320 100 P-59 320 100 P-60 320 100 P-61 320 100 P-62 320 100 P-63 320 100 P-64 320 100 P-65 320 100 P-66 320 100 P-67 320 100 P-68 320 100 P-69 320 100 P-70 320 100 P-71 320 100 P-72 320 90 P-75 320 100 P-76 320 100 P-77 320 100 P-78 320 100 P-79 320 100 P-80 320 100 P-81 320 100 P-82 320 100 P-83 320 100 P-84 320 100 P-85 320 100 P-86 320 100 P-87 320 100 P-88 320 100 P-89 320 100 P-90 320 100 P-94 320 100 P-95 320 100 P-97 320 100 P-98 320 100 P-99 320 100

TABLE-US-00007 TABLE 5 Pre-emergence action at 320 g/ha against AVEFA in % Example Dosage number [g/ha] AVEFA I-02 320 100 I-05 320 100 I-10 320 100 I-11 320 100 I-17 320 100 I-18 320 100 I-19 320 100 I-20 320 100 I-21 320 100 I-30 320 90 I-31 320 80 I-32 320 90 I-33 320 80 I-36 320 80 I-40 320 100 I-41 320 80 I-42 320 90 I-43 320 100 I-44 320 90 I-46 320 90 I-47 320 90 I-48 320 90 I-49 320 90 I-50 320 100 I-51 320 100 I-52 320 100 I-54 320 80 I-58 320 80 I-61 320 90 I-62 320 100 I-63 320 100 I-64 320 80 I-66 320 100 I-67 320 80 I-68 320 100 I-69 320 90 I-70 320 100 I-71 320 80 I-72 320 100 I-73 320 100 I-74 320 90 I-75 320 100 I-77 320 100 I-78 320 90 I-79 320 100 P-01 320 100 P-04 320 100 P-05 320 100 P-08 320 100 P-100 320 90 P-101 320 100 P-102 320 80 P-103 320 100 P-13 320 100 P-23 320 100 P-28 320 100 P-29 320 100 P-30 320 100 P-31 320 100 P-32 320 90 P-33 320 100 P-34 320 100 P-35 320 100 P-36 320 80 P-37 320 80 P-46 320 100 P-47 320 100 P-48 320 100 P-49 320 100 P-50 320 100 P-51 320 80 P-52 320 90 P-53 320 90 P-54 320 90 P-55 320 80 P-56 320 80 P-57 320 80 P-58 320 90 P-59 320 100 P-60 320 100 P-61 320 90 P-62 320 90 P-63 320 90 P-64 320 80 P-65 320 100 P-66 320 100 P-67 320 80 P-69 320 80 P-70 320 90 P-71 320 90 P-75 320 100 P-76 320 100 P-77 320 90 P-79 320 100 P-80 320 100 P-81 320 100 P-82 320 90 P-83 320 80 P-84 320 80 P-85 320 80 P-86 320 80 P-87 320 100 P-88 320 90 P-89 320 100 P-90 320 100 P-94 320 100 P-95 320 100 P-97 320 100 P-98 320 100 P-99 320 100

TABLE-US-00008 TABLE 6 Pre-emergence action at 320 g/ha against DIGSA in % I-02 320 100 I-05 320 100 I-10 320 100 I-11 320 100 I-17 320 100 I-18 320 100 I-19 320 100 I-20 320 100 I-21 320 100 I-30 320 100 I-31 320 100 I-32 320 100 I-33 320 100 I-34 320 100 I-35 320 100 I-36 320 100 I-37 320 90 I-40 320 100 I-41 320 100 I-42 320 100 I-43 320 100 I-44 320 100 I-45 320 100 I-46 320 100 I-47 320 100 I-48 320 100 I-49 320 100 I-50 320 100 I-51 320 100 I-52 320 100 I-54 320 100 I-55 320 100 I-56 320 100 I-57 320 100 I-58 320 100 I-59 320 100 I-61 320 100 I-62 320 100 I-63 320 100 I-64 320 100 I-66 320 100 I-67 320 100 I-68 320 100 I-69 320 100 I-70 320 100 I-71 320 100 I-72 320 100 I-73 320 100 I-74 320 100 I-75 320 100 I-76 320 100 I-77 320 100 I-78 320 100 I-79 320 100 P-01 320 100 P-04 320 100 P-05 320 100 P-08 320 100 P-100 320 100 P-101 320 100 P-102 320 100 P-103 320 100 P-104 320 100 P-13 320 100 P-23 320 100 P-28 320 100 P-29 320 100 P-30 320 100 P-31 320 100 P-32 320 100 P-33 320 100 P-34 320 100 P-35 320 100 P-36 320 100 P-37 320 100 P-46 320 100 P-47 320 100 P-48 320 100 P-49 320 100 P-50 320 100 P-51 320 100 P-52 320 100 P-53 320 100 P-54 320 100 P-55 320 100 P-56 320 100 P-57 320 100 P-58 320 100 P-59 320 100 P-60 320 100 P-61 320 100 P-62 320 100 P-63 320 100 P-64 320 100 P-65 320 100 P-66 320 100 P-67 320 100 P-68 320 100 P-69 320 100 P-70 320 100 P-71 320 100 P-72 320 100 P-75 320 100 P-76 320 100 P-77 320 100 P-78 320 100 P-79 320 100 P-80 320 100 P-81 320 100 P-82 320 100 P-83 320 100 P-84 320 100 P-85 320 100 P-86 320 100 P-87 320 100 P-88 320 100 P-89 320 100 P-90 320 100 P-94 320 100 P-95 320 100 P-97 320 100 P-98 320 100 P-99 320 100

TABLE-US-00009 TABLE 7 Pre-emergence action at 320 g/ha against ECHCG in % Example Dosage number [g/ha] ECHCG I-02 320 100 I-05 320 100 I-10 320 100 I-11 320 100 I-17 320 100 I-18 320 100 I-19 320 100 I-20 320 100 I-21 320 100 I-30 320 100 I-31 320 100 I-32 320 100 I-36 320 100 I-37 320 100 I-40 320 100 I-42 320 80 I-43 320 100 I-44 320 90 I-45 320 100 I-46 320 100 I-47 320 100 I-48 320 100 I-49 320 100 I-50 320 100 I-51 320 100 I-52 320 100 I-54 320 100 I-55 320 100 I-56 320 100 I-57 320 100 I-58 320 100 I-59 320 100 I-61 320 100 I-62 320 100 I-63 320 100 I-64 320 100 I-66 320 100 I-67 320 100 I-68 320 100 I-69 320 100 I-70 320 100 I-71 320 100 I-72 320 100 I-73 320 100 I-74 320 100 I-75 320 90 I-76 320 100 I-77 320 100 I-78 320 100 I-79 320 100 P-01 320 100 P-05 320 100 P-08 320 100 P-100 320 100 P-101 320 100 P-102 320 100 P-103 320 100 P-104 320 100 P-13 320 100 P-23 320 100 P-28 320 100 P-29 320 100 P-30 320 100 P-31 320 100 P-32 320 100 P-33 320 100 P-34 320 100 P-35 320 100 P-36 320 90 P-37 320 100 P-46 320 100 P-47 320 100 P-48 320 100 P-49 320 100 P-50 320 100 P-51 320 100 P-52 320 100 P-53 320 100 P-54 320 100 P-55 320 100 P-56 320 100 P-57 320 100 P-58 320 100 P-59 320 100 P-60 320 100 P-61 320 100 P-62 320 100 P-63 320 90 P-64 320 90 P-65 320 100 P-66 320 100 P-67 320 100 P-68 320 100 P-69 320 100 P-70 320 100 P-71 320 100 P-72 320 100 P-75 320 100 P-76 320 100 P-77 320 100 P-78 320 100 P-79 320 100 P-80 320 100 P-81 320 100 P-82 320 100 P-83 320 100 P-84 320 100 P-85 320 100 P-86 320 100 P-87 320 100 P-88 320 100 P-89 320 100 P-90 320 100 P-94 320 100 P-95 320 100 P-97 320 100 P-98 320 100 P-99 320 100

TABLE-US-00010 TABLE 8 Post-emergence action at 320 g/ha against LOLRI in % Example Dosage number [g/ha] LOLRI I-02 320 100 I-05 320 100 I-10 320 100 I-11 320 100 I-17 320 100 I-18 320 100 I-19 320 100 I-20 320 100 I-21 320 100 I-30 320 100 I-31 320 100 I-32 320 100 I-33 320 100 I-34 320 100 I-35 320 100 I-36 320 100 I-37 320 100 I-40 320 90 I-41 320 100 I-42 320 100 I-43 320 100 I-44 320 100 I-45 320 100 I-46 320 100 I-47 320 100 I-48 320 100 I-49 320 100 I-50 320 100 I-51 320 100 I-52 320 100 I-54 320 100 I-55 320 100 I-56 320 100 I-57 320 100 I-58 320 100 I-59 320 100 I-61 320 100 I-62 320 100 I-63 320 100 I-64 320 100 I-66 320 100 I-67 320 100 I-68 320 100 I-69 320 100 I-70 320 100 I-71 320 100 I-72 320 100 I-73 320 100 I-74 320 100 I-75 320 100 I-76 320 100 I-77 320 100 I-78 320 100 I-79 320 100 P-01 320 100 P-04 320 100 P-05 320 100 P-08 320 100 P-100 320 100 P-101 320 100 P-102 320 100 P-103 320 100 P-104 320 100 P-13 320 100 P-23 320 100 P-28 320 100 P-29 320 100 P-30 320 100 P-31 320 100 P-32 320 100 P-33 320 100 P-34 320 100 P-35 320 100 P-36 320 100 P-37 320 100 P-46 320 100 P-48 320 100 P-49 320 100 P-50 320 100 P-51 320 100 P-52 320 100 P-53 320 100 P-54 320 100 P-55 320 100 P-56 320 100 P-57 320 100 P-58 320 100 P-59 320 100 P-60 320 100 P-61 320 100 P-62 320 100 P-63 320 100 P-64 320 100 P-65 320 100 P-66 320 90 P-67 320 90 P-68 320 100 P-69 320 100 P-70 320 100 P-71 320 100 P-72 320 100 P-75 320 100 P-76 320 100 P-77 320 100 P-78 320 100 P-79 320 100 P-80 320 100 P-81 320 100 P-82 320 100 P-83 320 100 P-84 320 100 P-85 320 100 P-86 320 100 P-87 320 100 P-88 320 100 P-89 320 100 P-90 320 100 P-94 320 100 P-95 320 100 P-97 320 100 P-98 320 100 P-99 320 100

TABLE-US-00011 TABLE 9 Pre-emergence action at 320 g/ha against SETVI in % Example Number Dosage SETVI P-04 320 100 P-13 320 100 P-23 320 100 P-08 320 100 P-05 320 100 P-01 320 100 I-10 320 100 I-11 320 100 I-05 320 100 I-17 320 100 P-29 320 100 P-28 320 100 P-33 320 100 P-32 320 100 P-30 320 100 P-31 320 100 I-18 320 100 I-19 320 100 P-37 320 100 P-36 320 100 P-35 320 100 P-34 320 100 I-21 320 100 I-20 320 100 P-45 320 80 P-100 320 100 P-99 320 100 P-101 320 100 P-103 320 100 P-104 320 100 P-102 320 100 I-79 320 100 I-78 320 100 I-74 320 100 I-75 320 100 I-76 320 100 P-46 320 100 P-60 320 100 P-50 320 100 P-47 320 100 P-55 320 100 I-77 320 100 I-02 320 100 P-49 320 100 P-48 320 100 I-31 320 100 P-58 320 100 P-57 320 100 P-59 320 100 P-56 320 100 P-51 320 100 P-52 320 100 P-53 320 100 P-54 320 100 I-30 320 100 I-32 320 100 I-34 320 100 I-36 320 100 I-33 320 100 I-35 320 100 I-37 320 100 P-65 320 100 P-66 320 100 P-67 320 100 P-64 320 100 P-63 320 100 P-62 320 100 P-69 320 100 P-61 320 100 I-41 320 100 I-40 320 100 I-42 320 100 I-43 320 100 P-68 320 100 P-70 320 100 P-71 320 100 P-72 320 100 I-45 320 100 I-44 320 100 I-46 320 100 I-47 320 100 I-48 320 100 I-49 320 100 P-79 320 100 P-80 320 100 P-75 320 100 P-76 320 100 I-51 320 100 I-50 320 100 P-78 320 100 P-77 320 100 I-54 320 100 I-55 320 100 I-52 320 100 P-95 320 100 P-89 320 100 P-90 320 100 P-94 320 100 I-64 320 100 I-63 320 100 I-66 320 100 I-69 320 100 I-61 320 100 I-62 320 100 P-82 320 100 P-84 320 100 P-83 320 100 P-81 320 100 I-57 320 100 I-56 320 100 P-87 320 100 P-86 320 100 I-58 320 100 P-85 320 100 P-88 320 100 I-59 320 100 I-68 320 100 I-71 320 100 I-70 320 100 I-67 320 100 P-97 320 100 P-98 320 100 I-73 320 100 I-72 320 100

TABLE-US-00012 TABLE 10 Pre-emergence action at 320 g/ha against ABUTH in % Example Dosage number [g/ha] ABUTH I-02 320 100 I-05 320 80 I-17 320 90 I-18 320 80 I-44 320 80 I-50 320 100 I-68 320 90 I-72 320 100 I-73 320 100 P-08 320 80 P-100 320 80 P-28 320 90 P-29 320 80 P-30 320 80 P-31 320 90 P-32 320 80 P-34 320 90 P-51 320 80 P-58 320 80 P-70 320 80 P-75 320 80 P-87 320 80 P-88 320 80 P-97 320 100 P-98 320 90

TABLE-US-00013 TABLE 11 Pre-emergence action at 320 g/ha against AMARE in % Example Dosage number [g/ha] AMARE I-02 320 100 I-17 320 100 I-18 320 100 I-19 320 100 I-21 320 100 I-30 320 100 I-35 320 90 I-36 320 90 I-39 320 80 I-44 320 100 I-46 320 100 I-48 320 90 I-50 320 80 I-51 320 100 I-52 320 80 I-55 320 80 I-58 320 100 I-59 320 100 I-61 320 100 I-62 320 90 I-68 320 100 I-73 320 100 I-75 320 80 I-77 320 100 I-78 320 100 I-79 320 100 P-01 320 100 P-04 320 80 P-05 320 100 P-100 320 100 P-101 320 100 P-102 320 90 P-103 320 100 P-104 320 100 P-13 320 90 P-23 320 90 P-28 320 100 P-29 320 100 P-30 320 100 P-31 320 100 P-32 320 90 P-33 320 100 P-35 320 100 P-37 320 100 P-46 320 100 P-47 320 100 P-50 320 100 P-51 320 90 P-52 320 80 P-54 320 100 P-56 320 80 P-57 320 80 P-58 320 90 P-60 320 100 P-67 320 80 P-75 320 100 P-76 320 100 P-79 320 80 P-80 320 90 P-81 320 100 P-82 320 90 P-86 320 100 P-97 320 100 P-98 320 100 P-99 320 100

TABLE-US-00014 TABLE 12 Pre-emergence action at 320 g/ha against MATIN in % Example Dosage number [g/ha] MATIN I-02 320 90 I-17 320 90 I-19 320 80 I-30 320 90 I-42 320 80 I-44 320 80 I-46 320 90 I-48 320 80 I-50 320 80 I-51 320 100 I-58 320 100 I-59 320 80 I-61 320 80 I-67 320 80 I-68 320 100 I-70 320 80 I-71 320 90 I-72 320 100 I-73 320 90 I-75 320 90 I-77 320 80 I-78 320 80 I-79 320 90 P-01 320 80 P-04 320 90 P-05 320 90 P-08 320 80 P-100 320 90 P-101 320 80 P-103 320 90 P-13 320 80 P-28 320 90 P-29 320 90 P-32 320 80 P-49 320 80 P-53 320 90 P-55 320 90 P-56 320 80 P-60 320 90 P-75 320 90 P-80 320 90 P-81 320 80 P-84 320 80 P-86 320 80 P-97 320 100 P-98 320 90

TABLE-US-00015 TABLE 13 Pre-emergence action at 320 g/ha against PHBPU in % Example Dosage number [g/ha] PHBPU I-61 320 80 P-13 320 100

TABLE-US-00016 TABLE 14 Pre-emergence action at 320 g/ha against POLCO in % Example Dosage number [g/ha] POLCO I-02 320 100 I-05 320 80 I-10 320 80 I-18 320 100 I-19 320 100 I-44 320 100 I-46 320 90 I-48 320 90 I-50 320 90 I-51 320 80 I-61 320 90 I-69 320 100 I-70 320 80 I-79 320 90 P-08 320 100 P-13 320 80 P-28 320 80 P-29 320 90 P-30 320 80 P-31 320 90 P-32 320 80 P-33 320 100 P-51 320 90 P-52 320 80 P-54 320 80 P-60 320 80 P-70 320 80 P-71 320 90 P-72 320 100 P-75 320 80 P-76 320 100 P-80 320 90 P-81 320 100 P-82 320 100 P-86 320 90 P-87 320 80 P-89 320 100

TABLE-US-00017 TABLE 15 Pre-emergence action at 320 g/ha against VIOTR in % Example Dosage number [g/ha] VIOTR I-02 320 100 I-05 320 90 I-10 320 100 I-11 320 90 I-17 320 100 I-18 320 100 I-19 320 100 I-20 320 100 I-21 320 100 I-30 320 100 I-31 320 80 I-32 320 100 I-33 320 100 I-35 320 100 I-36 320 80 I-42 320 80 I-44 320 100 I-45 320 80 I-46 320 100 I-47 320 100 I-48 320 100 I-49 320 100 I-50 320 100 I-51 320 100 I-52 320 80 I-58 320 90 I-59 320 100 I-61 320 100 I-62 320 100 I-67 320 100 I-68 320 100 I-69 320 90 I-70 320 100 I-71 320 100 I-72 320 100 I-73 320 100 I-76 320 90 I-78 320 100 I-79 320 100 P-01 320 100 P-04 320 100 P-05 320 100 P-08 320 90 P-100 320 100 P-101 320 80 P-13 320 100 P-23 320 100 P-28 320 100 P-29 320 100 P-30 320 100 P-31 320 100 P-32 320 100 P-33 320 100 P-34 320 100 P-35 320 100 P-36 320 100 P-37 320 100 P-43 320 100 P-46 320 100 P-47 320 100 P-48 320 100 P-49 320 100 P-50 320 100 P-51 320 100 P-52 320 90 P-53 320 80 P-54 320 100 P-55 320 100 P-56 320 100 P-57 320 100 P-58 320 100 P-59 320 100 P-60 320 100 P-65 320 80 P-69 320 80 P-70 320 80 P-71 320 100 P-72 320 100 P-75 320 100 P-76 320 100 P-77 320 100 P-79 320 100 P-80 320 100 P-81 320 100 P-82 320 90 P-83 320 90 P-84 320 80 P-85 320 100 P-86 320 100 P-87 320 90 P-88 320 100 P-89 320 80 P-97 320 90 P-98 320 100 P-99 320 100

TABLE-US-00018 TABLE 16 Pre-emergence action at 320 g/ha against VERPE in % Example Dosage number [g/ha] VERPE I-02 320 90 I-10 320 100 I-11 320 100 I-17 320 90 I-24 320 80 I-44 320 80 I-51 320 100 I-62 320 100 I-69 320 80 I-71 320 90 I-73 320 90 I-78 320 90 I-79 320 80 P-01 320 100 P-04 320 90 P-05 320 80 P-08 320 90 P-100 320 90 P-103 320 90 P-23 320 90 P-28 320 100 P-29 320 100 P-30 320 80 P-31 320 90 P-32 320 90 P-33 320 80 P-34 320 80 P-35 320 80 P-36 320 80 P-37 320 80 P-48 320 80 P-49 320 80 P-50 320 80 P-54 320 80 P-55 320 80 P-60 320 80 P-61 320 90 P-67 320 80 P-69 320 90 P-70 320 90 P-71 320 90 P-72 320 80 P-75 320 90 P-76 320 100 P-77 320 80 P-79 320 90 P-80 320 100 P-81 320 90 P-83 320 80 P-85 320 90 P-86 320 100 P-87 320 80 P-88 320 100 P-97 320 100 P-98 320 100 P-99 320 100

[0274] For example, compound nos. P-70, P-81, P-05, P-77, P-76, I-10, I-2 and I-11 in tables 4-18, at an application rate of 320 g/ha, each show 90-100% efficacy against Alopecurus myosuroides, Avena fatua, Digitaria sanguinalis, Echinochloa crus-galli, Lolium rigidum, and Setaria viridis.

[0275] The compounds of the invention are therefore suitable for control of unwanted plant growth by the pre-emergence method.

[0276] 2. Post-Emergence Herbicidal Effect and Crop Plant Compatibility

[0277] 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 as aqueous suspension or emulsion at a water application rate equating to 600 to 800 l/ha with addition of 0.2% wetting agent. After the test plants have been left to stand in the greenhouse under optimal growth conditions for about 3 weeks, the action of the preparations is assessed visually in comparison to untreated controls (herbicidal action in percent (%): 100% activity=the plants have died, 0% activity=like control plants).

[0278] As the results from tables 5 and 6 show, compounds of the invention have good herbicidal post-emergence efficacy against a broad spectrum of weed grasses and weeds.

TABLE-US-00019 TABLE 17 Post-emergence action at 80 g/ha against ALOMY in % Example Dosage number [g/ha] ALOMY I-01 80 100 I-02 80 100 I-03 80 100 I-04 80 100 I-05 80 100 I-06 80 100 I-07 80 100 I-08 80 80 I-09 80 100 I-10 80 100 I-11 80 100 I-12 80 100 I-13 80 100 I-14 80 90 I-15 80 100 I-16 80 100 I-17 80 100 I-18 80 100 I-19 80 100 I-20 80 100 I-21 80 100 I-30 80 90 I-31 80 100 I-32 80 100 I-33 80 100 I-34 80 100 I-35 80 100 I-36 80 100 I-37 80 100 I-40 80 100 I-41 80 100 I-42 80 90 I-43 80 100 I-44 80 100 I-45 80 90 I-47 80 100 I-48 80 90 I-49 80 90 I-50 80 100 I-51 80 100 I-52 80 100 I-54 80 100 I-55 80 100 I-56 80 90 I-58 80 100 I-59 80 100 I-61 80 100 I-62 80 100 I-63 80 100 I-64 80 90 I-66 80 100 I-67 80 100 I-68 80 100 I-69 80 100 I-70 80 90 I-71 80 90 I-72 80 90 I-73 80 100 I-74 80 90 I-75 80 90 I-76 80 90 I-77 80 100 I-78 80 100 I-79 80 90 P-01 80 100 P-02 80 100 P-03 80 100 P-04 80 100 P-05 80 100 P-06 80 100 P-07 80 100 P-08 80 100 P-09 80 100 P-100 80 100 P-101 80 100 P-102 80 90 P-103 80 100 P-104 80 100 P-11 80 80 P-12 80 100 P-13 80 100 P-14 80 100 P-15 80 100 P-16 80 100 P-17 80 100 P-18 80 100 P-19 80 80 P-20 80 100 P-21 80 100 P-22 80 100 P-23 80 100 P-24 80 100 P-25 80 100 P-26 80 100 P-27 80 90 P-28 80 100 P-29 80 100 P-30 80 100 P-31 80 90 P-32 80 100 P-33 80 100 P-34 80 100 P-35 80 100 P-36 80 100 P-37 80 100 P-46 80 100 P-47 80 100 P-48 80 100 P-49 80 100 P-50 80 100 P-51 80 100 P-52 80 100 P-53 80 100 P-54 80 100 P-55 80 100 P-56 80 100 P-57 80 100 P-58 80 100 P-59 80 100 P-60 80 100 P-61 80 90 P-62 80 90 P-63 80 100 P-64 80 100 P-65 80 90 P-66 80 90 P-67 80 100 P-68 80 100 P-69 80 100 P-70 80 100 P-71 80 80 P-72 80 80 P-75 80 100 P-76 80 100 P-77 80 90 P-78 80 100 P-79 80 100 P-80 80 100 P-81 80 100 P-82 80 100 P-83 80 100 P-85 80 80 P-86 80 90 P-87 80 90 P-88 80 100 P-89 80 100 P-90 80 100 P-95 80 100 P-97 80 100 P-98 80 100 P-99 80 100

TABLE-US-00020 TABLE 18 Post-emergence action at 80 g/ha against AVEFA in % Example Dosage number [g/ha] AVEFA I-01 80 90 I-02 80 90 I-03 80 100 I-04 80 100 I-06 80 100 I-07 80 100 I-08 80 90 I-09 80 100 I-12 80 100 I-13 80 90 I-14 80 90 I-15 80 100 I-16 80 100 I-17 80 90 I-18 80 100 I-19 80 90 I-30 80 80 I-31 80 100 I-32 80 100 I-33 80 100 I-34 80 90 I-35 80 80 I-36 80 100 I-37 80 100 I-40 80 90 I-41 80 90 I-42 80 90 I-43 80 90 I-44 80 80 I-45 80 80 I-47 80 90 I-50 80 80 I-51 80 100 I-52 80 90 I-55 80 90 I-56 80 90 I-59 80 90 I-63 80 80 I-64 80 80 I-66 80 80 I-71 80 80 I-72 80 100 I-73 80 100 I-74 80 80 I-75 80 90 I-76 80 90 I-77 80 90 I-78 80 80 I-79 80 90 P-02 80 100 P-03 80 100 P-06 80 100 P-07 80 100 P-09 80 100 P-100 80 80 P-101 80 80 P-102 80 80 P-103 80 90 P-104 80 90 P-11 80 100 P-12 80 100 P-14 80 100 P-15 80 100 P-16 80 100 P-17 80 100 P-18 80 100 P-19 80 100 P-20 80 100 P-21 80 100 P-22 80 100 P-24 80 100 P-25 80 100 P-26 80 100 P-27 80 90 P-28 80 90 P-29 80 90 P-30 80 90 P-31 80 100 P-32 80 90 P-33 80 90 P-34 80 90 P-35 80 80 P-37 80 90 P-46 80 90 P-47 80 90 P-48 80 90 P-49 80 90 P-50 80 90 P-51 80 100 P-52 80 90 P-53 80 90 P-54 80 100 P-55 80 100 P-56 80 90 P-57 80 90 P-58 80 90 P-59 80 90 P-60 80 100 P-61 80 80 P-62 80 90 P-63 80 80 P-64 80 80 P-65 80 90 P-66 80 90 P-67 80 90 P-68 80 90 P-69 80 90 P-71 80 80 P-75 80 90 P-76 80 90 P-79 80 90 P-80 80 90 P-81 80 80 P-83 80 90 P-84 80 80 P-87 80 80 P-90 80 80 P-95 80 80 P-97 80 100 P-98 80 90 P-99 80 80

TABLE-US-00021 TABLE 19 Post-emergence action at 80 g/ha against DIGSA in % Example Dosage number [g/ha] DIGSA I-01 80 90 I-02 80 90 I-03 80 100 I-04 80 100 I-05 80 100 I-06 80 100 I-07 80 100 I-08 80 80 I-09 80 100 I-10 80 100 I-11 80 100 I-12 80 100 I-13 80 100 I-14 80 90 I-15 80 100 I-16 80 100 I-17 80 100 I-18 80 100 I-19 80 100 I-20 80 90 I-21 80 100 I-30 80 100 I-31 80 100 I-32 80 100 I-33 80 100 I-34 80 100 I-35 80 100 I-36 80 100 I-37 80 100 I-40 80 100 I-41 80 100 I-42 80 100 I-44 80 100 I-45 80 90 I-46 80 90 I-51 80 100 I-56 80 90 I-57 80 90 I-58 80 90 I-59 80 100 I-61 80 90 I-62 80 90 I-63 80 90 I-64 80 80 I-66 80 90 I-67 80 90 I-68 80 100 I-69 80 90 I-70 80 90 I-71 80 90 I-72 80 100 I-73 80 100 I-74 80 90 I-75 80 90 I-76 80 90 I-77 80 90 I-78 80 90 I-79 80 100 P-01 80 100 P-02 80 100 P-03 80 100 P-04 80 100 P-05 80 100 P-06 80 100 P-07 80 100 P-08 80 100 P-09 80 100 P-100 80 90 P-101 80 90 P-102 80 90 P-103 80 100 P-104 80 90 P-11 80 100 P-12 80 100 P-13 80 100 P-14 80 100 P-15 80 100 P-16 80 100 P-17 80 100 P-18 80 100 P-19 80 90 P-20 80 100 P-21 80 100 P-22 80 100 P-23 80 100 P-24 80 100 P-25 80 100 P-26 80 100 P-27 80 90 P-28 80 100 P-29 80 100 P-30 80 100 P-31 80 100 P-32 80 100 P-33 80 100 P-34 80 100 P-35 80 100 P-36 80 90 P-37 80 100 P-46 80 100 P-47 80 100 P-48 80 100 P-49 80 90 P-50 80 90 P-51 80 100 P-52 80 100 P-53 80 100 P-54 80 100 P-55 80 100 P-56 80 100 P-57 80 100 P-58 80 100 P-59 80 100 P-60 80 90 P-61 80 100 P-62 80 100 P-63 80 100 P-64 80 100 P-65 80 100 P-66 80 100 P-68 80 90 P-69 80 80 P-70 80 100 P-71 80 90 P-72 80 90 P-75 80 90 P-76 80 90 P-77 80 80 P-78 80 90 P-79 80 90 P-80 80 90 P-81 80 90 P-82 80 90 P-83 80 100 P-84 80 90 P-85 80 90 P-86 80 90 P-87 80 100 P-88 80 90 P-89 80 90 P-90 80 90 P-94 80 80 P-95 80 80 P-97 80 100 P-98 80 100 P-99 80 90

TABLE-US-00022 TABLE 20 Post-emergence action at 80 g/ha against ECHCG in % Example Dosage number [g/ha] ECHCG I-01 80 90 I-02 80 100 I-03 80 100 I-04 80 100 I-05 80 100 I-06 80 100 I-07 80 100 I-09 80 100 I-10 80 100 I-11 80 100 I-12 80 100 I-13 80 100 I-14 80 90 I-15 80 100 I-16 80 100 I-17 80 100 I-18 80 100 I-19 80 100 I-20 80 100 I-21 80 100 I-30 80 100 I-31 80 100 I-32 80 100 I-33 80 100 I-34 80 100 I-35 80 100 I-36 80 100 I-37 80 100 I-40 80 100 I-41 80 100 I-42 80 100 I-43 80 100 I-44 80 100 I-45 80 100 I-46 80 100 I-47 80 100 I-48 80 100 I-49 80 100 I-50 80 100 I-51 80 100 I-52 80 100 I-54 80 100 I-55 80 100 I-56 80 100 I-57 80 100 I-58 80 100 I-59 80 100 I-61 80 100 I-62 80 100 I-63 80 100 I-64 80 100 I-66 80 100 I-67 80 90 I-68 80 100 I-69 80 100 I-70 80 100 I-71 80 90 I-72 80 100 I-73 80 100 I-74 80 100 I-75 80 100 I-76 80 100 I-77 80 100 I-78 80 90 I-79 80 100 P-01 80 100 P-02 80 100 P-03 80 100 P-04 80 100 P-05 80 100 P-06 80 100 P-07 80 100 P-08 80 100 P-09 80 100 P-100 80 100 P-101 80 100 P-102 80 80 P-103 80 100 P-104 80 100 P-12 80 100 P-13 80 100 P-14 80 100 P-15 80 100 P-16 80 100 P-17 80 100 P-18 80 100 P-19 80 100 P-20 80 100 P-21 80 100 P-22 80 100 P-23 80 100 P-24 80 100 P-25 80 100 P-26 80 100 P-27 80 90 P-28 80 100 P-29 80 100 P-30 80 100 P-31 80 100 P-32 80 100 P-34 80 100 P-35 80 90 P-36 80 90 P-37 80 100 P-46 80 100 P-47 80 100 P-48 80 100 P-49 80 100 P-50 80 100 P-51 80 100 P-52 80 100 P-53 80 100 P-54 80 100 P-55 80 100 P-56 80 100 P-57 80 100 P-58 80 100 P-59 80 100 P-60 80 100 P-61 80 100 P-62 80 100 P-63 80 100 P-64 80 100 P-65 80 90 P-66 80 100 P-67 80 100 P-68 80 100 P-69 80 100 P-70 80 100 P-71 80 100 P-72 80 100 P-75 80 100 P-76 80 100 P-77 80 100 P-78 80 100 P-79 80 100 P-80 80 100 P-81 80 100 P-82 80 100 P-83 80 100 P-84 80 100 P-85 80 100 P-86 80 100 P-87 80 100 P-88 80 100 P-89 80 100 P-90 80 100 P-94 80 100 P-95 80 100 P-97 80 100 P-98 80 100 P-99 80 100

TABLE-US-00023 TABLE 21 Post-emergence action at 80 g/ha against LOLRI in % Example Dosage number [g/ha] LOLRI I-01 80 100 I-02 80 100 I-03 80 100 I-04 80 100 I-05 80 100 I-06 80 100 I-07 80 100 I-08 80 90 I-09 80 100 I-10 80 100 I-11 80 100 I-12 80 100 I-13 80 90 I-14 80 90 I-15 80 100 I-16 80 100 I-17 80 100 I-18 80 100 I-19 80 100 I-20 80 100 I-30 80 100 I-31 80 100 I-32 80 100 I-33 80 100 I-34 80 100 I-35 80 100 I-36 80 100 I-37 80 90 I-40 80 90 I-41 80 90 I-42 80 90 I-43 80 90 I-44 80 80 I-46 80 90 I-47 80 100 I-48 80 100 I-49 80 90 I-50 80 90 I-51 80 90 I-52 80 90 I-54 80 90 I-55 80 90 I-56 80 80 I-57 80 80 I-58 80 100 I-59 80 90 I-61 80 100 I-62 80 90 I-63 80 90 I-64 80 90 I-66 80 100 I-67 80 90 I-68 80 100 I-69 80 100 I-70 80 90 I-71 80 90 I-72 80 100 I-73 80 100 I-74 80 90 I-75 80 90 I-76 80 90 I-77 80 90 I-78 80 90 I-79 80 100 P-01 80 100 P-02 80 100 P-03 80 100 P-04 80 100 P-05 80 100 P-06 80 100 P-07 80 100 P-08 80 100 P-09 80 100 P-100 80 100 P-101 80 100 P-102 80 90 P-103 80 90 P-11 80 100 P-12 80 100 P-13 80 100 P-14 80 100 P-15 80 100 P-16 80 100 P-17 80 100 P-18 80 100 P-19 80 100 P-20 80 100 P-21 80 100 P-22 80 100 P-23 80 90 P-24 80 100 P-25 80 100 P-26 80 100 P-27 80 100 P-28 80 100 P-29 80 100 P-30 80 100 P-31 80 100 P-32 80 100 P-33 80 100 P-34 80 90 P-35 80 100 P-37 80 100 P-46 80 100 P-47 80 100 P-48 80 100 P-49 80 100 P-50 80 100 P-51 80 100 P-52 80 100 P-53 80 100 P-54 80 100 P-55 80 100 P-56 80 100 P-57 80 100 P-58 80 100 P-59 80 100 P-60 80 100 P-61 80 100 P-62 80 90 P-63 80 100 P-64 80 100 P-65 80 100 P-66 80 100 P-67 80 90 P-68 80 90 P-69 80 90 P-70 80 80 P-71 80 80 P-72 80 80 P-75 80 100 P-76 80 100 P-79 80 90 P-80 80 90 P-81 80 100 P-82 80 100 P-83 80 100 P-84 80 80 P-85 80 90 P-86 80 100 P-87 80 100 P-88 80 100 P-89 80 90 P-90 80 100 P-94 80 90 P-95 80 90 P-97 80 100 P-98 80 100 P-99 80 90

TABLE-US-00024 TABLE 22 Post-emergence action at 80 g/ha against SETVI in % Example Dosage number [g/ha] SETVI I-01 80 90 I-02 80 100 I-03 80 100 I-04 80 100 I-05 80 100 I-06 80 100 I-07 80 100 I-08 80 90 I-09 80 100 I-10 80 100 I-11 80 100 I-12 80 100 I-13 80 100 I-14 80 90 I-15 80 100 I-16 80 100 I-17 80 100 I-18 80 100 I-19 80 100 I-20 80 100 I-21 80 100 I-31 80 100 I-33 80 100 I-34 80 100 I-37 80 100 I-40 80 100 I-41 80 100 I-42 80 100 I-43 80 100 I-44 80 100 I-45 80 100 I-46 80 100 I-50 80 100 I-51 80 100 I-52 80 100 I-54 80 100 I-55 80 100 I-56 80 100 I-57 80 100 I-58 80 100 I-59 80 100 I-61 80 100 I-62 80 100 I-63 80 100 I-64 80 100 I-66 80 100 I-67 80 90 I-68 80 100 I-70 80 100 I-71 80 100 I-72 80 100 I-73 80 100 I-74 80 100 I-75 80 100 I-76 80 100 I-77 80 100 I-78 80 100 I-79 80 100 P-01 80 100 P-02 80 100 P-03 80 100 P-04 80 100 P-05 80 100 P-06 80 100 P-07 80 100 P-08 80 100 P-09 80 100 P-100 80 100 P-101 80 100 P-102 80 90 P-103 80 100 P-104 80 100 P-11 80 100 P-12 80 100 P-13 80 100 P-14 80 100 P-15 80 100 P-16 80 100 P-17 80 100 P-18 80 100 P-19 80 100 P-20 80 100 P-21 80 100 P-22 80 100 P-23 80 100 P-24 80 100 P-25 80 100 P-26 80 100 P-27 80 90 P-28 80 100 P-29 80 100 P-30 80 100 P-31 80 100 P-32 80 100 P-33 80 100 P-34 80 100 P-35 80 100 P-36 80 100 P-37 80 100 P-46 80 100 P-47 80 100 P-48 80 100 P-49 80 100 P-50 80 100 P-55 80 100 P-56 80 100 P-57 80 100 P-59 80 100 P-60 80 100 P-61 80 100 P-62 80 100 P-63 80 100 P-64 80 100 P-65 80 100 P-66 80 100 P-67 80 100 P-68 80 100 P-69 80 100 P-70 80 100 P-71 80 100 P-72 80 100 P-75 80 100 P-76 80 100 P-77 80 100 P-78 80 100 P-79 80 100 P-80 80 100 P-81 80 100 P-82 80 100 P-83 80 100 P-84 80 100 P-85 80 100 P-86 80 100 P-87 80 100 P-88 80 100 P-89 80 100 P-90 80 100 P-94 80 100 P-95 80 100 P-97 80 100 P-98 80 100 P-99 80 100

TABLE-US-00025 TABLE 23 Post-emergence action at 80 g/ha against ABUTH in % Example Dosage number [g/ha] ABUTH I-02 80 80 I-05 80 80 I-06 80 80 I-12 80 90 I-18 80 80 I-19 80 90 I-30 80 80 I-31 80 80 I-32 80 80 I-35 80 80 I-36 80 80 I-42 80 80 P-03 80 80 P-04 80 80 P-08 80 80 P-13 80 80 P-14 80 90 P-16 80 80 P-17 80 90 P-18 80 80 P-23 80 80 P-25 80 90 P-26 80 80 P-30 80 80 P-32 80 90 P-33 80 80 P-51 80 80 P-52 80 80 P-53 80 80 P-54 80 80 P-58 80 80 P-61 80 80 P-62 80 80 P-64 80 80 P-87 80 80

TABLE-US-00026 TABLE 24 Post-emergence action at 80 g/ha against AMARE in % Example Dosage number [g/ha] AMARE I-02 80 80 I-31 80 80 I-36 80 80 I-40 80 80 I-44 80 80 I-61 80 80 P-18 80 80 P-31 80 80 P-52 80 80 P-58 80 80 P-62 80 80 P-88 80 80

TABLE-US-00027 TABLE 25 Post-emergence action at 80 g/ha against PHBPU in % Example Dosage number [g/ha] PHBPU I-05 80 80 I-41 80 80 I-58 80 80 I-61 80 80 I-68 80 80 P-81 80 80

TABLE-US-00028 TABLE 26 Post-emergence action at 80 g/ha against POLCO in % Example Dosage number [g/ha] POLCO I-05 80 100 I-10 80 80 I-11 80 80 P-16 80 80 P-51 80 80

TABLE-US-00029 TABLE 27 Post-emergence action at 80 g/ha against VIOTR in % Example Dosage number [g/ha] VIOTR I-19 80 80 I-32 80 80 I-47 80 100 I-58 80 80 I-68 80 80 P-16 80 80 P-17 80 80 P-34 80 80 P-35 80 90 P-49 80 80 P-71 80 100 P-72 80 90 P-82 80 80

TABLE-US-00030 TABLE 28 Post-emergence action at 80 g/ha against VERPE in % Example Dosage number [g/ha] VERPE I-02 80 90 I-11 80 80 I-30 80 80 I-32 80 80 I-61 80 80 I-71 80 80 P-21 80 80 P-28 80 80 P-29 80 80 P-30 80 80 P-52 80 80 P-54 80 80

TABLE-US-00031 TABLE 29 Post-emergence action at 80 g/ha against HORMU in % Example Dosage number [g/ha] HORMU I-01 80 100 I-03 80 100 I-04 80 100 I-06 80 100 I-07 80 100 I-08 80 80 I-09 80 100 I-12 80 100 I-13 80 90 I-14 80 90 I-15 80 100 I-16 80 100 P-02 80 100 P-03 80 100 P-06 80 100 P-07 80 100 P-09 80 100 P-11 80 100 P-12 80 100 P-14 80 100 P-15 80 100 P-16 80 100 P-17 80 100 P-18 80 100 P-19 80 100 P-20 80 100 P-21 80 100 P-22 80 100 P-24 80 100 P-25 80 100 P-26 80 100 P-27 80 90

[0279] For example, compounds P-22, P-25, P-26 in tables 17 to 29, at an application rate of 80 g/ha, each show 80-100% efficacy against Alopecurus myosuroides, Avena fatua, Digitaria sanguinalis, Echinochloa crus-galli, Setaria viridis and Hordeum murinum, and are therefore suitable for control of unwanted plant growth by the post-emergence method.

SPECIFICALLY SUBSTITUTED 3-PHENYL-5-SPIROCYCLOPENTYL-3-PYRROLIN-2-ONES AND THEIR USE AS HERBICIDES

Inventors

Cpc classification

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C07C57/30

CHEMISTRY; METALLURGY

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C07D209/96

CHEMISTRY; METALLURGY

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A01N43/38

HUMAN NECESSITIES

International classification

Classification Explorer

A01N43/38

HUMAN NECESSITIES

Classification Explorer

C07C57/30

CHEMISTRY; METALLURGY

Abstract

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