Patent Publication Number: US-4923503-A

Title: Agents for influencing plant growth

Description:
The present invention relates to agents which are based on azolylacetophenone oxime ethers and which influence the growth of plants or act as herbicides. 
     It has been disclosed that azolylacetophenone oxime ethers can be used as fungicides (German Laid-Open Application No. DOS 2,431,407). Bioregulator, plant growth regulator or herbicidal activity of such oxime ethers is unknown to date. 
     We have found that azolylacetophenone oxime ethers of the formula (I) ##STR2## where R and R 1  independently of one another are each hydrogen, halogen, alkyl, cycloalkyl, alkoxy, alkylthio, alkylsulfonyl, haloalkyl, nitro, cyano, unsubstituted or substituted phenyl or unsubstituted or substituted phenoxy, R 2  is hydrogen, alkyl, aralkyl or unsubstituted or substituted allyl or is propargyl, R 3  is a divalent radical of the formula --(CH 2 ) m  --, --(CH 2  CH 2  O--) u  CH 2  CH 2  --, --(CH 2 ) v  --CH═CH--(CH 2 ) t  -- or --(CH 2 ) v  --C.tbd.C--(CH 2 ) t  --, n, p, u, v and t independently of one another are each 1, 2 or 3, m is an integer from 2 to 10, and Az is 1,2,4-triazol-1-yl, pyrazol-1-yl or imidazol-1-yl, and their salts and metal complexes can be used successfully as bioregulators, i.e. agents for influencing plant growth, in the widest sense. 
     The action can extend to modification of the form of growth of the plants, alteration of substances present in the plants, and destruction of undesirable plants. 
     In formula (I), R and R 1  independently of one another are each, for example, halogen (fluorine, chlorine or bromine), nitro, cyano, alkyl or alkylsulfonyl, each of 1 to 4 carbon atoms, alkoxy or alkylthio, each of 1 or 2 carbon atoms, haloalkyl of 1 to 4, in particular 1 or 2, carbon atoms, and 1 to 5 halogen atoms, in particular 1 to 3 identical or different halogen atoms, preferred halogen atoms being fluorine and chlorine. Haloalkyl is particularly preferably trifluoromethyl. 
     R and R 1  independently of one another can furthermore be phenoxy or phenyl which is unsubstituted or, preferably, monosubstituted or polysubstituted (disubstituted or trisubstituted) by identical or different substituents, preferred substituents in each case being halogen, in particular fluorine, chlorine or bromine, cyano, nitro and haloalkyl of 1 or 2 carbon atoms and not more than 3 identical or different halogen atoms, preferred halogen atoms being fluorine and chlorine, and an example of haloalkyl being trifluoromethyl. 
     In formula (I), R 2  is preferably straight-chain or branched alkyl of 1 to 5 carbon atoms, e.g. methyl, ethyl, n-propyl, isopropyl, sec.-butyl or neopentyl. R 2  may furthermore be aralkyl where alkyl is of 1 to 4 carbon atoms, unsubstituted phenyl being the preferred aryl. Examples of aralkyl are thus benzyl, phenethyl, phenylpropyl and phenylbutyl. R 2  can also be allyl which is unsubstituted or substituted by 1, 2 or 3 chlorine atoms, or can be propargyl. Examples of allyl radicals are allyl, 2,3-dichloroallyl and 2,3,3-trichloroallyl. 
     In formula (I), R 3  is a divalent radical of the formula --(CH 2 ) m  --, for example --CH 2  CH 2  --, --(CH 2 ) 3  --, --(CH 2 ) 4  --, --(CH 2 ) 5  --, (CH 2 ) 6  --, (CH 2 ) 7  -- or --(CH 2 ) 8  --. 
     R 3  can furthermore be a divalent radical containing one, two or three oxygen atoms, of the formula --(CH 2  CH 2  O) u  CH 2  CH 2  --, for example --CH 2  CH 2  OCH 2  CH 2  --, --CH 2  CH 2  OCH 2  CH 2  OCH 2  CH 2  -- or --(CH 2  CH 2  O) 3  CH 2  CH 2  --. 
     Finally, R 3  can be a divalent radical which contains a double or triple bond and is of the formula --(CH 2 ) v  --CH═CH--(CH 2 ) t  or --(CH 2 ) v  --C.tbd.C--(CH 2 ) t  --. 
     Examples are --CH 2  --CH═CH--CH 2  --, --(CH 2 ) 2  --CH═CH--(CH 2 ) 2  --, --(CH 2 ) 3  --CH═CH--(CH 2 ) 3  --, --CH 2  --CH═CH--CH 2  --, --(CH 2 ) 2  --C.tbd.C--(CH 2 ) 2  -- and --(CH 2 ) 3  --C═C--(CH 2 ) 3  --. 
     m is an integer from 2 to 10, preferably from 2 to 8. 
     If the agents are intended for use as growth regulators in the narrower sense, R, R 1 , R 2 , R 3 , m, n, p, u and Az preferably have the following meanings: 
     R and R 1  independently of another are each F, Cl, Br, C 1  -C 5  -alkyl, methoxy, ethoxy, methylthio, ethylthio, C 1  -C 3  -haloalkyl containing not more than 4 fluorine or chlorine atoms, or unsubstituted or substituted phenyl or phenoxy, 
     R 2  is hydrogen, 
     R 3  is --(CH 2 ) m  --, --(CH 2  CH 2  O) u  --CH 2  CH 2  --, --CH 2  --CH═CH--CH 2  -- or --CH 2  --C.tbd.C--CH 2  --, 
     n, p and u are each 1, 2 or 3, 
     m is from 2 to 8, and 
     Az is 1,2,4-triazol-1-yl, pyrazol-1-yl or imidazol-1-yl; 
     salts of the compounds can also be used. 
     Herbicidal agents are obtained in particular when R 3  is a divalent radical --(CH 2 ) m  --, where m is 2, 3 or 4. 
     Examples of salts of the azolylacetophenone oxime ethers of the formula (I) are the hydrochlorides, hydrobromides, sulfates, phosphates and p-toluenesulfonates. 
     A metal complex is, for example, an adduct of one equivalent of a zinc or copper salt, e.g. CuCl 2  or ZnCl 2 , with two equivalents of a compound (I). 
     PREPARATION EXAMPLE 
     2,4-Dichloro-ω-[1,2,4-triazol-1-yl]-acetophenoneoxime O-[2-(4-chlorophenoxy)ethyl] ether, E and Z isomers 
     23 g (0.085 mole) of 2,4-dichloro-ω-[1,2,4-triazol-1-yl]-acetophenone oxime, 20 g of 2-[4-chlorophenoxy]-bromoethane, 7.1 g of powdered KOH and 5.8 g of triethylbenzylammonium chloride in 100 ml of toluene are stirred vigorously at 80°-100° C. for 1 hour. The mixture is evaporated down, the residue is taken up in 250 ml of dichloromethane, the solution is washed with three times 100 ml of water, and the organic phase is dried with sodium sulfate and evaporated down. Chromatography over silica gel, using dichloromethane as eluant, gives 6 g of the Z isomer (active ingredient No. 23) and 4 g of the E isomer of 2,4-dichloro-ω-[1,2,4-triazol-1-yl]-acetophenone oxime O-[2-(4-chlorophenoxy)-ethyl] ether (active ingredient No. 24). The Z isomer is the first to be eluted. 
     The compounds listed in the Table below can be prepared in a similar manner. The configuration in which the oxime oxygen and the C aromatic ring are on the same side of the oxime double bond is designated E, while the corresponding, other isomer is designated Z. 
     Tri=1,2,4-triazol-1-yl, Pyr=pyrazol-1-yl, Im=imidazolyl, Ts=tosyl, Bu=butyl and Me=methyl. 
     Those compounds of the formula I which are shown in the Table below and for which melting points (mp.) or characteristics bands are given were prepared in a similar manner. Their structures were confirmed by elemental analysis. The compounds for which no physicochemical data are given can be obtained in the manner described for the compounds actually prepared; because of their similar constitution, they are expected to have actions similar to those of the compounds investigated in detail. 
     
                                           TABLE A                                 
__________________________________________________________________________
Compounds of the formula I with R.sup.3 = (CH.sub.2).sub.m:               
 ##STR3##                                                                 
No. R.sub.n R.sub.p.sup.1                                                 
                  R.sup.2 Az     Configuration                            
                                        m  M.p. [°C.]              
__________________________________________________________________________
1   H       H     H       Tri    E/Z mixture                              
                                        2                                 
2   H       H     H       Tri    E/Z mixture                              
                                        4  oil                            
3   H       H     H       Tri    E/Z mixture                              
                                        6                                 
4   H       H     H       Tri    E/Z mixture                              
                                        8                                 
5   4-Cl    H     H       Tri    E/Z mixture                              
                                        2  96-98                          
6   4-Br    H     H       Tri    E/Z mixture                              
                                        2  89-90                          
7   4-OMe   H     H       Tri    E/Z mixture                              
                                        2                                 
8   4-CN    H     H       Tri    E/Z mixture                              
                                        2                                 
9   4-CF.sub.3                                                            
            H     H       Tri    E/Z mixture                              
                                        2                                 
10  4-NO.sub.2                                                            
            H     H       Tri    E/Z mixture                              
                                        2                                 
11  4-OC.sub.6 H.sub.5                                                    
            H     H       Tri    E/Z mixture                              
                                        2                                 
12  2,4-Cl.sub.2                                                          
            H     H       Tri.HNO.sub. 3                                  
                                 E/Z mixture                              
                                        2  96                             
13  2,4-Cl.sub.2                                                          
            H     H       Tri    Z      3  oil                            
14  2,4-Cl.sub.2                                                          
            H     H       Tri    E      3  oil                            
15  2,4-Cl.sub.2                                                          
            H     H       Tri    Z      4  oil                            
16  2,4-Cl.sub.2                                                          
            H     H       Tri    E      4  oil                            
17  2,4-Cl.sub.2                                                          
            H     H       Tri    Z      5  oil                            
18  2,4-Cl.sub.2                                                          
            H     H       Tri    E      5  oil                            
19  2,4-Cl.sub.2                                                          
            H     H       Tri    Z      6  oil                            
20  2,4-Cl.sub.2                                                          
            H     H       Tri    E      6  oil                            
21  2,4-Cl.sub.2                                                          
            H     H       Tri    E      8                                 
22  2,4-Cl.sub.2                                                          
            H     H       Tri    E      8                                 
23  2,4-Cl.sub.2                                                          
            4-Cl  H       Tri    Z      2  87-91                          
24  2,4-Cl.sub.2                                                          
            4-Cl  H       Tri    E      2  58-61                          
25  2,4-Cl.sub.2                                                          
            4-Cl  H       Tri.HNO.sub.3                                   
                                 E/Z mixture                              
                                        2                                 
26  2,4-Cl.sub.2                                                          
            4-Cl  H       Tri.HNO.sub.3                                   
                                 E/Z mixture                              
                                        2                                 
27  2,4-Cl.sub.2                                                          
            4-Cl  H       Tri.H.sub.2 SO.sub.4                            
                                 E/Z mixture                              
                                        2                                 
28  2,4-Cl.sub.2                                                          
            4-Cl  H       Tri.H.sub.3 PO.sub.4                            
                                 E/Z mixture                              
                                        2                                 
29  2,4-Cl.sub.2                                                          
            4-Cl  H       Tri.TsOH                                        
                                 E/Z mixture                              
                                        2                                 
30  2,4-Cl.sub.2                                                          
            4-Cl  H       Tri.1/2 CuCl.sub.2                              
                                 E/Z mixture                              
                                        2                                 
31  2,4-Cl.sub.2                                                          
            4-Cl  H       Tri.1/2 ZnCl.sub.2                              
                                 E/Z mixture                              
                                        2                                 
32  2,4-Cl.sub.2                                                          
            4-Cl  CH.sub.3                                                
                          Tri    E/Z mixture                              
                                        2                                 
33  2,4-Cl.sub.2                                                          
            4-Cl  n-Bu    Tri    E/Z mixture                              
                                        2                                 
34  2,4-Cl.sub.2                                                          
            4-Cl  CH.sub.2 C.sub.6 H.sub.5                                
                          Tri    E/Z mixture                              
                                        2                                 
35  2,4-Cl.sub.2                                                          
            4-Cl  CH.sub.2 C(CH.sub.3).sub.3                              
                          Tri    E/Z mixture                              
                                        2                                 
36  2,4-Cl.sub.2                                                          
            4-Cl  H       Tri    Z      3  oil                            
37  2,4-Cl.sub.2                                                          
            4-Cl  H       Tri    E      3  oil                            
38  2,4-Cl.sub.2                                                          
            4-Cl  H       Tri    Z      4  65-71                          
39  2,4-Cl.sub.2                                                          
            4-Cl  H       Tri    E      4  oil                            
40  2,4-Cl.sub.2                                                          
            4-Cl  H       Tri    Z      5  oil                            
41  2,4-Cl.sub.2                                                          
            4-Cl  H       Tri    E      5  59-62                          
42  2,4-Cl.sub.2                                                          
            2,4-Cl.sub.2                                                  
                  H       Tri    Z      2   95-100                        
43  2,4-Cl.sub.2                                                          
            2,4-Cl.sub.2                                                  
                  H       Tri    E      2  oil                            
44  2,4-Cl.sub.2                                                          
            2,4-Cl.sub.2                                                  
                  CH.sub.3                                                
                          Tri    E/Z mixture                              
                                        2                                 
45  2,4-Cl.sub.2                                                          
            2,4-Cl.sub.2                                                  
                  n-Bu    Tri    E/Z mixture                              
                                        2                                 
46  2,4-Cl.sub.2                                                          
            2,4-Cl.sub.2                                                  
                  CH.sub.2C.sub.6 H.sub.5                                 
                          Tri    E/Z mixture                              
                                        2                                 
47  2,4-Cl.sub.2                                                          
            2,4-Cl.sub.2                                                  
                  CH.sub.2C(CH.sub.3)                                     
                          Tri    E/Z mixture                              
                                        2                                 
48  2,4-Cl.sub.2                                                          
            2,4-Cl.sub.2                                                  
                  H       Tri.HNO.sub.3                                   
                                 E/Z mixture                              
                                        2  132 (decomposition)            
49  2,4-Cl.sub.2                                                          
            2,4,6-Cl.sub.3                                                
                  H       Tri.HCl                                         
                                 E/Z mixture                              
                                        2                                 
50  2,4-Cl.sub.2                                                          
            2,4,6-Cl.sub.3                                                
                  H       Tri.1/2 ZnCl.sub.2                              
                                 E/Z mixture                              
                                        2                                 
51  2,4-Cl.sub.2                                                          
            2,4,6-Cl.sub.3                                                
                  H       Tri.1/2 CuCl.sub.2                              
                                 E/Z mixture                              
                                        2                                 
52  2,4-Cl.sub.2                                                          
            4-F   H       Tri    Z      2  66-70                          
53  2,4-Cl.sub.2                                                          
            4-F   H       Tri    E      2  73-77                          
54  2,4-Cl.sub.2                                                          
            4-CN  H       Tri    Z      2   96-100                        
55  2,4-Cl.sub.2                                                          
            4-CN  H       Tri    E      2                                 
56  2,4-Cl.sub.2                                                          
            4-tert.-Bu                                                    
                  H       Tri.HNO.sub.3                                   
                                 E/Z mixture                              
                                        2  117                            
57  2,4-Cl.sub.2                                                          
            4-OMe H       Tri    Z      2  oil                            
58  2,4-Cl.sub.2                                                          
            4-OMe H       Tri    E      2                                 
59  2,4-Cl.sub.2                                                          
            4-SMe H       Tri    E/Z mixture                              
                                        2                                 
60  2,4-Cl.sub.2                                                          
            4-Br  H       Tri    E/Z mixture                              
                                        2                                 
61  2,4-Cl.sub.2                                                          
            4-NO.sub.2                                                    
                  H       Tri    E/Z mixture                              
                                        2                                 
62  2,4-Cl.sub.2                                                          
            3-Cl  H       Tri    Z      2  oil                            
63  2,4-Cl.sub.2                                                          
            3-Cl  H       Tri    E      2  73-77                          
64  2,4-Cl.sub.2                                                          
            3-CF.sub.3                                                    
                  H       Tri    Z      2  oil                            
65  2,4-Cl.sub.2                                                          
            3-CF.sub.3                                                    
                  H       Tri    E      2  66-69                          
66  2,4-Cl.sub.2                                                          
            4-Cl  CH.sub.2 HCCH.sub.2                                     
                          Tri    E/Z mixture                              
                                        2                                 
67  2,4-Cl.sub.2                                                          
            4-Cl  CH.sub.2 CClCCl.sub.2                                   
                          Tri    E/Z mixture                              
                                        2                                 
68  2,4-Cl.sub.2                                                          
            4-Cl  propargyl                                               
                          Tri    E/Z mixture                              
                                        2                                 
69  2,4-Cl.sub.2 -3-CH.sub.3                                              
            4-Cl  H       Tri    E/Z mixture                              
                                        2  oil                            
70  2,5-Cl.sub.2                                                          
            4-Cl  H       Tri    Z      2  oil                            
71  2,5-Cl.sub.2                                                          
            H     H       Tri    E      2  82-86                          
72  2,4-Cl.sub.2                                                          
            H     H       Pyr    E/Z mixture                              
                                        2                                 
73  2,4-Cl.sub.2                                                          
            H     H       Pyr    E/Z mixture                              
                                        3                                 
74  2,4-Cl.sub.2                                                          
            H     H       Pyr    E/Z mixture                              
                                        4                                 
75  2,4-Cl.sub.2                                                          
            H     H       Pyr    E/Z mixture                              
                                        5                                 
76  2,4-Cl.sub.2                                                          
            4-Cl  H       Pyr    E/Z mixture                              
                                        2                                 
77  2,4-Cl.sub.2                                                          
            4-F   H       Pyr    E/Z mixture                              
                                        2                                 
78  2,4-Cl.sub.2                                                          
            4-CN  H       Pyr    E/Z mixture                              
                                        2                                 
79  2,4-Cl.sub.2                                                          
            4-OMe H       Pyr    E/Z mixture                              
                                        2                                 
80  2,4-Cl.sub.2                                                          
            4-Cl  CH.sub.3                                                
                          Pyr    E/Z mixture                              
                                        2                                 
114 2,4-Cl.sub.2                                                          
            2,4,6-Cl.sub.3                                                
                  H       Tri    Z isomer                                 
                                        2  76-85                          
127 4-Cl    2,4,6-Cl.sub.3                                                
                  H       Tri    Z isomer                                 
                                        2  114-116                        
128 H       4-Cl  H       Tri    Z isomer                                 
                                        2  79-83                          
129 H       4-Cl  H       Tri    Z isomer                                 
                                        3  59-64                          
130 H       4-Cl  H       Tri    Z isomer                                 
                                        4  59-62                          
131 H       3-Cl  H       Tri    Z isomer                                 
                                        2  73-75                          
132 H       3-CH.sub.3                                                    
                  H       Tri    Z isomer                                 
                                        2  54-56                          
133 H       H     H       Tri.1/2 CuCl.sub.2                              
                                 E/Z mixture                              
                                        4  wax-like                       
134 H       H     H       Tri.HCl                                         
                                 E/Z mixture                              
                                        4  wax-like                       
135 H       H     H       Tri    E/Z mixture                              
                                        4  oil                            
136 H       4-Cl  H       Tri.1/2 CuCl.sub.2.                             
                                 E/Z mixture                              
                                        4  wax-like                       
137 H       4-Cl  H       Tri.HCl                                         
                                 E/Z mixture                              
                                        4  108-115                        
138 H       4-Cl  H       Tri    E/Z mixture                              
                                        4  oil                            
139 H       4-Cl  H       Tri.1/2 CuCl.sub.2                              
                                 E/Z mixture                              
                                        2  wax-like                       
140 H       4-Cl  H       Tri.HCl                                         
                                 E/Z mixture                              
                                        2  138-142                        
141 H       4-Cl  H       Tri    E/Z mixture                              
                                        2  oil                            
142 H       3-Cl  H       Tri    E/Z mixture                              
                                        2  oil                            
143 H       3-Cl  H       Tri.HCl                                         
                                 E/Z mixture                              
                                        2  wax-like                       
144 H       3-Cl  H       Tri.1/2 CuCl.sub.2                              
                                 E/Z mixture                              
                                        2  wax-like                       
145 H       3-CH.sub.3                                                    
                  H       Tri    E/Z mixture                              
                                        2  oil                            
146 H       3-CH.sub.3                                                    
                  H       Tri.HCl                                         
                                 E/Z mixture                              
                                        2  wax-like                       
147 H       3-CH.sub.3                                                    
                  H       Tri.1/2 CuCl.sub.2                              
                                 E/Z mixture                              
                                        2  wax-like                       
148 4-CH.sub.3                                                            
            4-Cl  H       Tri    Z isomer                                 
                                        2  110-112                        
149 4-CH.sub.3                                                            
            4-Cl  H       Tri.HCl                                         
                                 Z isomer                                 
                                        2  164-167                        
150 4-CH.sub.3                                                            
            3-Cl  H       Tri    Z isomer                                 
                                        2  86-91                          
151 4-CH.sub.3                                                            
            3-Cl  H       Tri.HCl                                         
                                 Z isomer                                 
                                        2  oil                            
152 4-CH.sub.3                                                            
            3-CH.sub.3                                                    
                  H       Tri    Z isomer                                 
                                        2  66-71                          
153 4-CH.sub.3                                                            
            3-CH.sub.3                                                    
                  H       Tri.HCl                                         
                                 Z isomer                                 
                                        2  125-128                        
154 4-CH.sub.3                                                            
            4-Cl  H       Tri    Z isomer                                 
                                        3  70-72                          
155 4-CH.sub.3                                                            
            4-Cl  H       Tri.HCl                                         
                                 Z isomer                                 
                                        3  160-163                        
156 4-CH.sub.3                                                            
            H     H       Tri    Z isomer                                 
                                        4  58-61                          
157 4-CH.sub.3                                                            
            H     H       Tri.HCl                                         
                                 Z isomer                                 
                                        4  120-124                        
158 4-CH.sub.3                                                            
            4-Cl  H       Tri    Z isomer                                 
                                        4  75-76                          
159 4-CH.sub.3                                                            
            4-Cl  H       Tri.HCl                                         
                                 Z isomer                                 
                                        4  123-125                        
160 4-Cl    4-Cl  H       Tri    Z isomer                                 
                                        2  133-135                        
161 4-Cl    4-Cl  H       Tri.HCl                                         
                                 Z isomer                                 
                                        2  174-178                        
162 4-Cl    4-Cl  H       Tri    Z isomer                                 
                                        4  75-81                          
163 4-Cl    4-Cl  H       Tri.HCl                                         
                                 Z isomer                                 
                                        4  128-130                        
164 4-Cl    H     H       Tri    Z isomer                                 
                                        4  51-56                          
165 4-Cl    H     H       Tri.HCl                                         
                                 Z isomer                                 
                                        4  136                            
166 4-Cl    3-Cl  H       Tri    Z isomer                                 
                                        2  89-94                          
167 4-Cl    3-Cl  H       Tri.HCl                                         
                                 Z isomer                                 
                                        2  141-145                        
168 4-Cl    3-CH.sub.3                                                    
                  H       Tri    Z isomer                                 
                                        2  103-105                        
169 4-Cl    3-CH.sub.3                                                    
                  H       Tri.HCl                                         
                                 Z isomer                                 
                                        2  107-108                        
179 4-Cl    3-CF.sub.3                                                    
                  H       Tri           2  89-93                          
180 4-Cl    3,5-Cl.sub.2                                                  
                  H       Tri           2  88-94                          
181 4-CH.sub.3                                                            
            3,5-Cl.sub.2                                                  
                  H       Tri           2  70-74                          
182 4-Cl    3-Cl  H       Tri           3  67-69                          
183 4-CH.sub.3                                                            
            3-Cl  H       Tri           2  54-57                          
184 4-Cl    3-Cl  H       Im            2  119-123                        
185 4-Cl    3-Cl  H       Pyr           2  73-78                          
186 H       3-Cl  H       Im            2                                 
187 H       3-Cl  H       Pyr           2  oil                            
188 4-Cl    3,4-Cl.sub.2                                                  
                  H       Tri    Z isomer                                 
                                        2  83                             
189 4-Cl    2,3-Cl.sub.2                                                  
                  H       Tri    Z isomer                                 
                                        2  103-106                        
190 4-Cl    3-OCH.sub.3                                                   
                  H       Tri    Z isomer                                 
                                        2  99                             
191 3,4-Cl.sub.2                                                          
            3-Cl  H       Tri    Z isomer                                 
                                        2  84                             
192 4-F     3-Cl  H       Tri    Z isomer                                 
                                        2  71-74                          
193 3,4-Cl.sub.2                                                          
            3-CH.sub.3                                                    
                  H       Tri    Z isomer                                 
                                        2  73-75                          
194 4-F     3-CH.sub.3                                                    
                  H       Tri    Z isomer                                 
                                        2  63-65                          
195 4-Cl    3-NO.sub.2                                                    
                  H       Tri    Z isomer                                 
                                        2  135-137                        
196 4-C.sub.6 H.sub.5                                                     
            3-Cl  H       Tri    Z/E mixture                              
                                        2  60-63                          
197 4-C.sub.6 H.sub.5                                                     
            3-CH.sub.3                                                    
                  H       Tri    Z/E mixture                              
                                        2  wax-like                       
198 4-Cl    2,4,5-Cl.sub.3                                                
                  H       Tri    Z/E mixture                              
                                        2  89                             
199 4-Cl    2,5-Cl.sub.2                                                  
                  H       Tri    Z/E mixture                              
                                        2  124-126                        
200 4-OCH.sub.3                                                           
            3-CF.sub.3                                                    
                  H       Tri    Z/E mixture                              
                                        2  64-67                          
201 4-C.sub.6 H.sub.5                                                     
            3-CF.sub.3                                                    
                  H       Tri    Z/E mixture                              
                                        2  87-90                          
202 4-F     3-CF.sub.3                                                    
                  H       Tri    Z/E mixture                              
                                        2  70-74                          
203 3,4-Cl.sub.2                                                          
            3-CF.sub.3                                                    
                  H       Tri    Z/E mixture                              
                                        2  90-94                          
204 4-OCH.sub.3                                                           
            3-Cl  H       Tri    Z/E mixture                              
                                        2  48-50                          
205 4-OCH.sub.3                                                           
            3-CH.sub.3                                                    
                  H       Tri    Z/E mixture                              
                                        2  oil                            
206 H       3-CH.sub.3                                                    
                  H       Tri    Z/E mixture                              
                                        2                                 
207 4-(CH.sub.3).sub.2 CH                                                 
            3-Cl  H       Tri    Z/E mixture                              
                                        2                                 
208 4-(CH.sub.3).sub.2 CH                                                 
            3-CH.sub.3                                                    
                  H       Tri    Z/E mixture                              
                                        2                                 
209 4-(CH.sub.3).sub.2 CH                                                 
            3,4-Cl.sub.2                                                  
                  H       Tri    Z/E mixture                              
                                        2                                 
210 4-(CH.sub.3).sub.2 CH                                                 
            2,3-Cl.sub.2                                                  
                  H       Tri    Z/E mixture                              
                                        2                                 
211 4-(CH.sub.3).sub.2 C                                                  
            3-CH.sub.3                                                    
                  H       Tri    Z/E mixture                              
                                        2                                 
212 4-(CH.sub.3).sub.2 C                                                  
            3-Cl  H       Tri    Z/E mixture                              
                                        2                                 
213 4-(CH.sub.3).sub.3 C                                                  
            3,4-Cl.sub.2                                                  
                  H       Tri    Z/E mixture                              
                                        2                                 
214 4-(CH.sub.3).sub.3 C                                                  
            2,3-Cl.sub.2                                                  
                  H       Tri    Z/E mixture                              
                                        2                                 
215 4-cycl.-C.sub.6 H.sub.11                                              
            3-CH.sub.3                                                    
                  H       Tri    Z/E mixture                              
                                        2                                 
216 4-cycl.-C.sub.6 H.sub.11                                              
            3-Cl  H       Tri    Z/E mixture                              
                                        2                                 
217 4-cycl.-C.sub.6 H.sub.11                                              
            3,4-Cl.sub.2                                                  
                  H       Tri    Z/E mixture                              
                                        2                                 
218 4-cycl.-C.sub.6 H.sub.11                                              
            2,3-Cl.sub.2                                                  
                  H       Tri    Z/E mixture                              
                                        2                                 
219 4-C.sub.6 H.sub.5                                                     
            2,3-Cl.sub.2                                                  
                  H       Tri    Z/E mixture                              
                                        2                                 
220 4-C.sub.6 H.sub.5                                                     
            2,3-Cl.sub.2                                                  
                  H       Tri    Z/E mixture                              
                                        2                                 
221 4-OCH.sub.3                                                           
            2,3-Cl.sub.2                                                  
                  H       Tri    Z/E mixture                              
                                        2                                 
222 4-OCH.sub.3                                                           
            3,4-Cl.sub.2                                                  
                  H       Tri    Z/E mixture                              
                                        2                                 
223 4-OC.sub.6 H.sub.5                                                    
            3-Cl  H       Tri    Z/E mixture                              
                                        2                                 
224 4-OC.sub.6 H.sub.5                                                    
            3-OCH.sub.3                                                   
                  H       Tri    Z/E mixture                              
                                        2                                 
225 4-OC.sub.6 H.sub.5                                                    
            2,3-Cl.sub.2                                                  
                  H       Tri    Z/E mixture                              
                                        2                                 
226 4-OC.sub.6 H.sub.5                                                    
            3,4-Cl.sub.2                                                  
                  H       Tri    Z/E mixture                              
                                        2                                 
237 4-NO.sub.2                                                            
            3-Cl  H       Tri    Z/E mixture                              
                                        2                                 
238 4-NO.sub.2                                                            
            3-CH.sub.3                                                    
                  H       Tri    Z/E mixture                              
                                        2                                 
239 4-NO.sub.2                                                            
            3,4-Cl.sub.2                                                  
                  H       Tri    Z/E mixture                              
                                        2                                 
240 4-NO.sub.2                                                            
            2,3-Cl.sub.2                                                  
                  H       Tri    Z/E mixture                              
                                        2                                 
241 2-Cl    3-Cl  H       Tri    Z/E mixture                              
                                        2                                 
242 2-Cl    3-CH.sub.3                                                    
                  H       Tri    Z/E mixture                              
                                        2                                 
243 2-Cl    2,3-Cl.sub.2                                                  
                  H       Tri    Z/E mixture                              
                                        2                                 
244 2-Cl    3,4-Cl.sub.2                                                  
                  H       Tri    Z/E mixture                              
                                        2                                 
245 3,5-Cl.sub.2                                                          
            3-Cl  H       Tri    Z/E mixture                              
                                        2                                 
246 3,5-Cl.sub.2                                                          
            3-CH.sub.3                                                    
                  H       Tri    Z/E mixture                              
                                        2                                 
247 4-Br    3-Cl  H       Tri    Z/E mixture                              
                                        2                                 
248 4-Br    3-CH.sub.3                                                    
                  H       Tri    Z/E mixture                              
                                        2                                 
249 H       3-Cl  CH.sub.3                                                
                          Tri    Z/E mixture                              
                                        2                                 
250 H       3-CH.sub.3                                                    
                  CH.sub.3                                                
                          Tri    Z/E mixture                              
                                        2                                 
251 H       3-Cl  CH.sub.2 CH.sub.3                                       
                          Tri    Z/E mixture                              
                                        2                                 
252 H       3-CH.sub.3                                                    
                  CH.sub.2 CH.sub.3                                       
                          Tri    Z/E mixture                              
                                        2                                 
253 H       3-Cl  CH.sub.2 CH.sub.2 CH.sub.3                              
                          Tri    Z/E mixture                              
                                        2                                 
254 H       3-CH.sub.3                                                    
                  CH.sub.2 CH.sub.2 CH.sub.3                              
                          Tri    Z/E mixture                              
                                        2                                 
255 4-F     3-F   H       Tri    Z/E mixture                              
                                        2                                 
256 H       2-F   H       Tri    Z      2                                 
257 H       2-F   H       Tri    E      2                                 
258 H       2-Cl  H       Tri    Z      2                                 
259 H       2-Cl  H       Tri    E      2                                 
260 4-CH.sub.3                                                            
            2-F   H       Tri    Z      2                                 
261 4-CH.sub.3                                                            
            2-F   H       Tri    E      2                                 
262 4-CH.sub.3                                                            
            2-Cl  H       Tri    Z      2                                 
263 4-CH.sub.3                                                            
            2-Cl  H       Tri    E      2                                 
264 4-cycl.C.sub.6 H.sub.11                                               
            2-F   H       Tri    Z      2                                 
265 4-cycl.C.sub.6 H.sub.11                                               
            2-F   H       Tri    E      2  77-80                          
266 4-cycl.C.sub.6 H.sub.11                                               
            2-Cl  H       Tri    Z      2                                 
267 4-cycl.C.sub.6 H.sub.11                                               
            2-Cl  H       Tri    E      2  wax-like                       
268 4-C.sub.6 H.sub.5                                                     
            2-F   H       Tri    Z      2  111                            
269 4-C.sub.6 H.sub.5                                                     
            2-F   H       Tri    E      2                                 
270 4-C.sub.6 H.sub.5                                                     
            2-Cl  H       Tri    Z      2  108                            
271 4-C.sub.6 H.sub.5                                                     
            2-Cl  H       Tri    E      2                                 
272 4-Cl    2-F   H       Tri    Z      2                                 
273 4-Cl    2-F   H       Tri    E      2                                 
274 4-Cl    2-Cl  H       Tri    Z      2                                 
275 4-Cl    2-Cl  H       Tri    E      2                                 
276 4-F     2-Cl  H       Tri    E/Z mixture                              
                                        2  74-77                          
277 4-F     2-Cl  H       Tri    Z      2  81                             
278 4-F     2-Cl  H       Tri    E      2                                 
279 4-F     2-F   H       Tri    Z      2  86                             
280 4-F     2-F   H       Tri    E      2                                 
281 4-OCH.sub.3                                                           
            2-F   H       Tri    Z      2  79-81                          
282 4-OCH.sub.3                                                           
            2-F   H       Tri    E      2                                 
283 4-OCH.sub.3                                                           
            2-Cl  H       Tri    Z      2  71                             
284 4-OCH.sub.3                                                           
            2-Cl  H       Tri    E      2                                 
285 4-CN    2-F   H       Tri    Z      2                                 
286 4-CN    2-F   H       Tri    E      2                                 
287 H       2-CN  H       Tri    Z      2                                 
288 H       2-CN  H       Tri    E      2                                 
289 4-CH.sub.3                                                            
            2-CN  H       Tri    Z      2                                 
290 4-CH.sub.3                                                            
            2-CN  H       Tri    E      2                                 
291 4-Cl    2-CN  H       Tri    Z      2                                 
292 4-Cl    2-CN  H       Tri    E      2                                 
293 4-F     2-CN  H       Tri    Z      2                                 
294 4-F     2-CN  H       Tri    E      2                                 
295 H       2-CH.sub.3                                                    
                  H       Tri    Z      2                                 
296 H       2-CH.sub.3                                                    
                  H       Tri    E      2                                 
297 4-CH.sub.3                                                            
            2-CH.sub.3                                                    
                  H       Tri    Z      2                                 
298 4-CH.sub.3                                                            
            2-CH.sub.3                                                    
                  H       Tri    E      2                                 
299 4-Cl    2-CH.sub.3                                                    
                  H       Tri    Z      2                                 
300 4-Cl    2-CH.sub.3                                                    
                  H       Tri    E      2                                 
301 4-F     2-CH.sub.3                                                    
                  H       Tri    Z      2                                 
302 4-F     2-CH.sub.3                                                    
                  H       Tri    E      2                                 
303 H       2-OCH.sub.3                                                   
                  H       Tri    Z      2                                 
304 H       2-OCH.sub.3                                                   
                  H       Tri    E      2                                 
305 2-CH.sub.3                                                            
            2-OCH.sub.3                                                   
                  H       Tri    Z      2                                 
306 2-CH.sub.3                                                            
            2-OCH.sub.3                                                   
                  H       Tri    E      2                                 
307 2-Cl    2-OCH.sub.3                                                   
                  H       Tri    Z      2                                 
308 2-Cl    2-OCH.sub.3                                                   
                  H       Tri    E      2                                 
309 2-F     2-OCH.sub.3                                                   
                  H       Tri    Z      2                                 
310 2-F     2-OCH.sub.3                                                   
                  H       Tri    E      2                                 
311 3-Cl    2-Cl  H       Tri    Z      2                                 
312 3-Cl    2-F   H       Tri    Z      2                                 
313 3-Br    2-Cl  H       Tri    Z      2                                 
314 3,4-Cl.sub.2                                                          
            2-Cl  H       Tri    Z      2  98                             
315 3,4-Cl.sub.2                                                          
            2-F   H       Tri    Z      2  103-105                        
316 3,5-Cl.sub.2                                                          
            2-F   H       Tri    Z      2  117                            
317 3,5-Cl.sub.2                                                          
            2-Cl  H       Tri    Z      2  108                            
318 2,5-Cl.sub.2                                                          
            2-F   H       Tri.HNO.sub.3                                   
                                 Z      2  110                            
319 2,5-Cl.sub.2                                                          
            2-Cl  H       Tri    Z      2  wax-like                       
320 2,4-Cl.sub.2                                                          
            2-F   H       Tri    Z      2                                 
321 2,4-Cl.sub.2                                                          
            2-Cl  H       Tri    Z      2                                 
322 2-Cl    2-F   H       Tri    Z      2                                 
323 2-Cl    2-Cl  H       Tri    Z      2                                 
324 H       2,6-Cl.sub.2                                                  
                  H       Tri    Z      2                                 
325 4-CH.sub.3                                                            
            2,6-Cl.sub.2                                                  
                  H       Tri    Z      2                                 
326 4-Cl    2,6-Cl.sub.2                                                  
                  H       Tri    Z      2                                 
327 4-F     2,6-Cl.sub.2                                                  
                  H       Tri    Z      2                                 
328 2,5-Cl.sub.2                                                          
            3-Cl  H       Tri    Z      2  oil                            
329 3-Br    3-Cl  H       Tri    Z      2  100-103                        
__________________________________________________________________________
 
    
     
                       TABLE B                                                     
______________________________________                                    
Compounds of the formula I with R.sup.3 = (CH.sub.2 CH.sub.2 O).sub.u     
CH.sub.2 CH.sub.2                                                         
 ##STR4##                                                                 
                                            M.p.                          
No.  R.sub.n R.sub.p.sup.1                                                
                      R.sup.2                                             
                          Az   Configuration                              
                                        m   [°C.]                  
______________________________________                                    
 81  2,4-Cl.sub.2                                                         
             H        H   Tri  E/Z mixture                                
                                        1                                 
 82  2,4-Cl.sub.2                                                         
             H        H   Tri  E/Z mixture                                
                                        2   oil                           
 83  2,4-Cl.sub.2                                                         
             H        H   Tri  E/Z mixture                                
                                        3                                 
 84  2,4-Cl.sub.2                                                         
             4-Cl     H   Tri  E/Z mixture                                
                                        1                                 
 85  2,4-Cl.sub.2                                                         
             4-Cl     H   Tri  E/Z mixture                                
                                        2   oil                           
 86  2,4-Cl.sub.2                                                         
             4-Cl     H   Tri  E/Z mixture                                
                                        3                                 
 87  2,4-Cl.sub.2                                                         
             2,4-Cl.sub.2                                                 
                      H   Tri  E/Z mixture                                
                                        1                                 
 88  2,4-Cl.sub.2                                                         
             2,4-Cl.sub.2                                                 
                      H   Tri  E/Z mixture                                
                                        2   oil                           
 89  2,4-Cl.sub.2                                                         
             2,4-Cl.sub.2                                                 
                      H   Tri  E/Z mixture                                
                                        3                                 
106  2,4-Cl.sub.2                                                         
             2-Cl     H   Tri  E/Z mixture                                
                                        2   oil                           
107  2,4-Cl.sub.2                                                         
             3-Cl     H   Tri  E/Z mixture                                
                                        2   oil                           
108  2,4-Cl.sub.2                                                         
             4-OCH.sub.3                                                  
                      H   Tri  Z isomer 2   oil                           
109  2,4-Cl.sub.2                                                         
             2,4,6-Cl.sub.3                                               
                      H   Tri  Z isomer 2   oil                           
110  2,4-Cl.sub.2                                                         
             2-Cl     H   Tri  E/Z mixture                                
                                        1   wax-like                      
111  2,4-Cl.sub.2                                                         
             4-OCH.sub.3                                                  
                      H   Tri  Z isomer 1   wax-like                      
112  2,4-Cl.sub.2                                                         
             3-CH.sub.3                                                   
                      H   Tri  Z isomer 1   wax-like                      
113  2,4-Cl.sub.2                                                         
             4-CH.sub.3                                                   
                      H   Tri  Z isomer 1   wax-like                      
116  4-Cl    2,4,6-Cl.sub.3                                               
                      H   Tri  Z isomer 1   69-71                         
117  4-Cl    2-Cl     H   Tri  Z isomer 1   63-65                         
118  4-Cl    3-CH.sub.3                                                   
                      H   Tri  Z isomer 1   66-68                         
119  4-Cl    4-OCH.sub.3                                                  
                      H   Tri  Z isomer 1   71                            
120  4-Cl    4-CH.sub.3                                                   
                      H   Tri  Z isomer 1   79                            
121  4-Cl    H        H   Tri  Z isomer 2   oil                           
122  4-Cl    4-Cl     H   Tri  Z isomer 2   85-88                         
123  4-Cl    2-Cl     H   Tri  Z isomer 2   oil                           
124  4-Cl    3-Cl     H   Tri  Z isomer 2   oil                           
125  4-Cl    2,4-Cl.sub.2                                                 
                      H   Tri  Z isomer 2   48-53                         
126  4-Cl    4-OCH.sub. 3                                                 
                      H   Tri  Z isomer 2   oil                           
170  4-CH.sub.3                                                           
             4-Cl     H   Tri  Z isomer 2   oil                           
171  H       4-Cl     H   Tri  Z isomer 2   oil                           
______________________________________                                    
 
    
     
                       TABLE C                                                     
______________________________________                                    
Compounds of the formula I with R.sup.3 =                                 
(CH.sub.2).sub.vCHCH(CH.sub.2).sub.t                                      
 ##STR5##                                                                 
                                                M.p.                      
No.  R.sub.n R.sub.p.sup.1                                                
                      R.sup.2                                             
                          Az   Configuration                              
                                        v   t   [°C.]              
______________________________________                                    
90   2,4-Cl.sub.2                                                         
             4        H   Tri  E/Z mixture                                
                                        1   1   oil                       
91   2,4-Cl.sub.2                                                         
             4-Cl     H   Tri  E/Z mixture                                
                                        1   1   oil                       
92   2,4-Cl.sub.2                                                         
             4-CH.sub.3                                                   
                      H   Tri  E/Z mixture                                
                                        1   1                             
93   2,4-Cl.sub.2                                                         
             4-OCH.sub.3                                                  
                      H   Tri  E/Z mixture                                
                                        1   1                             
94   2,4-Cl.sub.2                                                         
             2,4-Cl.sub.2                                                 
                      H   Tri  E/Z mixture                                
                                        1   1   oil                       
95   2,4-Cl.sub.2                                                         
             2,4,6-Cl.sub.2                                               
                      H   Tri  E/Z mixture                                
                                        1   1   oil                       
96   2,4-Cl.sub.2                                                         
             4-Cl     H   Tri  E/Z mixture                                
                                        2   2                             
97   2,4-Cl.sub.2                                                         
             4-Cl     H   Tri  E/Z mixture                                
                                        3   3                             
115  2,4-Cl.sub.2                                                         
             2-Cl     H   Tri  E/Z mixture                                
                                        1   1   84                        
______________________________________                                    
 
    
     
                                           TABLE D                                 
__________________________________________________________________________
Compounds of the formula I with R.sup.3 = (CH.sub.2).sub.vCC(CH.sub.2).sub
.t                                                                        
 ##STR6##                                                                 
No.                                                                       
   R.sub.n                                                                
        R.sub.p.sup.1                                                     
              R.sup.2                                                     
                 Az  Configuration                                        
                            v  t   M.p. [°C.]                      
__________________________________________________________________________
 98                                                                       
   2,4-Cl.sub.2                                                           
        H     H  Tri E/Z mixture                                          
                            1  1  oil                                     
 99                                                                       
   2,4-Cl.sub.2                                                           
        4-Cl  H  Tri E/Z mixture                                          
                            1  1  oil                                     
100                                                                       
   2,4-Cl.sub.2                                                           
        4-CH.sub.3                                                        
              H  Tri E/Z mixture                                          
                            1  1  oil                                     
101                                                                       
   2,4-Cl.sub.2                                                           
        4-OCH.sub.3                                                       
              H  Tri E/Z mixture                                          
                            1  1  oil                                     
102                                                                       
   2,4-Cl.sub.2                                                           
        2,4-Cl.sub.2                                                      
              H  Tri E/Z mixture                                          
                            1  1  oil                                     
103                                                                       
   2,4-Cl.sub.2                                                           
        3-CH.sub.3                                                        
              H  Tri E/Z mixture                                          
                            1  1  oil                                     
104                                                                       
   2,4-Cl.sub.2                                                           
        4-Cl  H  Tri E/Z mixture                                          
                            2  2                                          
105                                                                       
   2,4-Cl.sub.2                                                           
        4-Cl  H  Tri E/Z mixture                                          
                            3  3                                          
172                                                                       
   2,4-Cl.sub.2                                                           
        4-F   H  Tri Z isomer                                             
                            1  1  oil                                     
173                                                                       
   2,4-Cl.sub.2                                                           
        3-Cl  H  Tri Z isomer                                             
                            1  1  oil                                     
174                                                                       
   4-Cl H     H  Tri Z isomer                                             
                            1  1  70-75                                   
175                                                                       
   4-Cl 4-Cl  H  Tri Z isomer                                             
                            1  1  81-85                                   
176                                                                       
   4-Cl 4-F   H  Tri Z isomer                                             
                            1  1  70-75                                   
177                                                                       
   4-Cl 3-Cl  H  Tri Z isomer                                             
                            1  1  80-85                                   
178                                                                       
   4-Cl 4-OCH.sub.3                                                       
              H  Tri Z isomer                                             
                            1  1  oil                                     
__________________________________________________________________________
 
    
     
         ______________________________________                                    
Characteristic NMR data (.sup.1 H-NMR):                                   
No.   δ in ppm, solvent CDCl.sub.3                                  
______________________________________                                    
13    4.05 &#34;t&#34; 2H; 4.45 &#34;t&#34; 2H; 5.39 s 2H, 7.72 s 1H;                     
      7.98 s 1H                                                           
14    3.90 &#34;t&#34; 2H; 4.25 &#34;t&#34; 2H; 5.10 s 2H; 7.82 s 1H;                     
      7.90 s 1H                                                           
15    4.00 &#34;t&#34; 2H; 4.35 &#34;t&#34; 2H; 5.40 s 2H; 7.80 s 1H;                     
      8.07 s 1H                                                           
16    3.90 &#34;t&#34; 2H; 4.20 &#34;t&#34; 2H; 5.20 s 2H; 7.90 s 1H;                     
      8.00 s 1H                                                           
17    4.00 &#34;t&#34; 2H; 4.30 &#34;t&#34; 2H; 5.44 s 2H; 7.82 s 1H;                     
      8.10 s 1H                                                           
18    3.90 &#34;t&#34; 2H; 4.20 &#34;t&#34; 2H; 5.20 s 2H; 7.93 s 1H;                     
      8.04 s 1H                                                           
36    4.03 &#34;t&#34; 2H; 4.43 &#34;t&#34; 2H; 5.44 s 2H; 7.80 s 1H;                     
      8.07 s 1H                                                           
37    3.90 &#34;t&#34; 2H; 4.27 &#34;t&#34; 2H; 5.20 s 2H; 7.90 s 1H;                     
      8.00 s 1H                                                           
39    3.78 &#34;t&#34; 2H; 4.08 &#34;t&#34;  2H; 5.05 s 2H; 7.70 s 1H;                    
      7.85 s 1H                                                           
40    3.38 &#34;t&#34; 2H; 4.20 &#34;t&#34; 2H; 5.35 s 2H; 7.70 s 1H;                     
      7.98 s 1H                                                           
43    4.22 &#34;t&#34; 2H; 4.48 &#34;t&#34; 2H; 5.23 s 2H; 7.98 s 1H;                     
      8.03 s 1H                                                           
57    4.25 &#34;t&#34; 2H; 4.60 &#34;t&#34; 2H; 5.47 s 2H; 7.80 s 1H;                     
      8.17 s 1H                                                           
62    4.27 &#34;t&#34; 2H; 4.60 &#34;t&#34; 2H; 5.48 s 2H; 7.80 s 1H;                     
      8.15 s 1H                                                           
64    4.43 &#34;t&#34; 2H; 4.63 &#34;t&#34; 2H; 5.45 s 2H; 7.80 s 1H;                     
      8.13 s 1H                                                           
69    2.41 3H; 4.22 &#34;t&#34; 2H; 4.58 &#34;t&#34; 2H; 5.41 s 2H;                       
      7.78 s 1H; 8.11 s 1H                                                
70    4.22 &#34;t&#34; 2H; 4.59 &#34;t&#34; 2H; 5.42 s 2H; 7.81 s 1H;                     
      8.14 s 1H                                                           
98    4.78 s 4H; 5.22 s 2H; 7.93 s 1H; 8.03 s 1H                          
100   2.28 s 3H; 4.70 m 3H; 5.20 s 2H; 7.90 s 1H;                         
      8.00 s 1H                                                           
101   3.72 s 3H; 4.70 s 2H; 4.87 s 2H; 5.44 s 2H;                         
      7.80 s 1H; 8.11 s 1H                                                
102   4.70 m 4H; 5.20 s and 5.50 s 2H; 7.80 s and 7.94 s 1H;              
      8.01 s and 8.10 s 1H                                                
103   2.31 s 3H; 4.72 s 2H; 4.87 s 2H; 5.44 s 2H; 7.80 s 1H;              
      8.10 s 1H                                                           
112   3.75 m 4H; 4.15 m 2H; 4.35 m 2H, 5.53 s 2H; 7.83 s 1H;              
      8.50 s 1H                                                           
113   3.75 m 4H; 4.15 m 2H; 4.38 m 2H; 5.53 s 2H; 7.85 s 1H;              
      8.50 s 1H                                                           
121   3.75 m 8H; 4.15 m 2H; 4.40 m 2H; 5.35 s 2H; 7.88 s 1H;              
      8.38 s 1H                                                           
123   3.80 m 8H; 4.15 m 2H; 4.45 m 2H; 5.38 s 2H; 7.88 s 1H;              
      8.38 s 1H                                                           
124   3.70 m 8H; 4.15 m 2H; 4.30 m 2H; 5.45 s 2H; 7.78 s 1H;              
      8.45 s 1H                                                           
126   3.80 m 8H; 4.10 m 2H; 4.40 m 2H; 5.60 s 2H; 8.05 s 1H;              
      8.70 s 1H                                                           
170   3.70 m 8H; 4.00 m 2H; 4.35 m 2H; 5.30 s 2H; 7.75 s 1H;              
      8.43 s 1H                                                           
171   3.80 m 8H; 4.10 m 2H; 4.45 m 2H; 5.40 s 2H; 7.90 s 1H;              
      8.40 s 1H                                                           
172   4.60 &#34;t&#34; 2H; 4.80 &#34;t&#34; 2H; 5.40 s 2H;, 7.70 s 1H;                    
      7.98 s 1H                                                           
173   4.65 &#34;t&#34; 2H; 4.85 &#34;t&#34; 2H; 5.40 s 2H;, 7.70 s 1H;                    
      8.00 s 1H                                                           
141   4.20 &#34;t&#34; 2H; 4.45 &#34;t&#34; 2H; 5.21 s 2H; 7.91 s 1H;                     
      8.13 s 1H                                                           
142   4.20 &#34;t&#34; 2H; 4.42 &#34;t&#34; 2H; 5.19 s 2H; 7.90 s 1H;                     
      8.02 s 1H                                                           
145   4.20 &#34;t&#34; 2H; 4.45 &#34;t&#34; 2H; 5.20 s 2H; 7.90 s 1H;                     
      8.02 s 1H                                                           
135   1.8 m 4H; 3.90 &#34;t&#34; 2H; 4.18 &#34;t&#34; 2H; 5.18 s 2H;                      
      7.89 s 1H; 8.00 s 1H                                                
106   3.7 m 8H; 4.2 m 4H; 5.55 s 2H; 7.87 s 1H; 8.52 s 1 H                
107   3.7 m 8H; 4.2 m 4H; 5.57 s 2H; 7.85 s 1H; 8.50 s 1H                 
108   3.7 m 8H; 4.0 m 2H;; 4.45 m 2H; 5.55 s 2H; 7.88 s 1H;               
      8.5 s 1H                                                            
109   3.7 m 8H; 4.25 m 4H; 5.55 s 2H; 7.85 s 1H; 8.50 s 1H                
110   3.8 m 4H; 4.20 m 4H; 5.45 s 2H; 7.75 s 1H; 8.40 s 1H                
111   3.75 m 4H; 4.05 m 2H; 4.35 m 2H; 5.53 s 2H; 7.83 s 1H;              
      8.50 s 1H                                                           
178   4.65 &#34;t&#34; 2H; 4.85 &#34;t&#34; 2H; 5.30 s 2H; 7.80 s 1H;                     
      8.10 s 1H                                                           
186   4.30 &#34;t&#34; 2H; 4.65 &#34;t&#34; 2H; 5.22 s 2H; 6.8-7.7 m; 12H                 
187   4.20 m 2H; 4.55 m 2H; 5.35 s 2H; 6.08 t 1H;                         
      6.6-7.8 m; 1H                                                       
197   4.25 &#34;t&#34; 2H; 4.60 &#34;t&#34; 2H; 5.42 s 2H; 7.88 s 1H;                     
      8.28 s 1H                                                           
205   4.25 &#34;t&#34; 2H; 4.55 &#34;t&#34; 2H; 5.32 s 2H; 7.90 s 1H;                     
      8.28 s 1H.                                                          
______________________________________                                    
 s = singlet                                                              
 &#34;t&#34; = pseudo-triplet                                                     
 m = multiplet                                                            
 
    
     The novel compounds may influence virtually all development stages of a plant in different ways, and are therefore employed as growth regulators or herbicides. 
    
    
     USE EXAMPLES 
     I. To determine the growth-regulating properties of the candidate compounds, soil provided with sufficient nutrients was filled into plastic pots about 12.5 cm in diameter and summer rape plants were growth therein. 
     The compounds were sprayed onto the plants (post-emergence treatment). The growth-regulating action observed was confirmed at the end of the experiment by height measurements. The values obtained were compared with those for untreated plants. 
     The compounds used for comparison purposes were active ingredients A and B having the structural formulae given below. 
     Not only was growth height reduced--the leaves also took on a more intense color. The increased chlorophyll content is indicative of a higher rate of photosynthesis, making for bigger yields. 
     Comparative agents: ##STR7## 
     The results show that active ingredients 13, 15, 52, 57, 62, 64, 101, 103, 116, 117, 119, 121, 122 and 123, applied for example at a rate of 1.5 or 6 mg per vessel, reduced growth height to a greater extent (e.g., 68% or 57%) than active ingredients A and B (e.g., 94% and 83%). 
     II. In the same manner as described under I, summer wheat of the Kalibri variety (Table 1) and summer barley of the Aramir variety (Table 2) were treated postemergence. The following results were obtained: 
     
                       TABLE 1                                                     
______________________________________                                    
No. of chemical                                                           
            mg of active ingre-                                           
                            Relative growth                               
example     dient per vessel                                              
                            height                                        
______________________________________                                    
--          --              100                                           
A           1.5             99.2                                          
            6               84.8                                          
B           1.5             99.5                                          
            6               94.0                                          
131         1.5             73.2                                          
            6               71.6                                          
142         1.5             79.2                                          
            6               73.2                                          
255         1.5             77.4                                          
            6               71.9                                          
276         1.5             70.1                                          
            6               70.1                                          
______________________________________                                    
 
    
     
                       TABLE 2                                                     
______________________________________                                    
No. of chemical                                                           
            mg of active ingre-                                           
                            Relative growth                               
example     dient per vessel                                              
                            height                                        
______________________________________                                    
--          --              100                                           
A           1.5             93.4                                          
            6               93.4                                          
B           1.5             95.3                                          
            6               95.3                                          
131         1.5             86.8                                          
            6               77.2                                          
142         1.5             92.9                                          
            6               92.9                                          
255         1.5             87.9                                          
            6               84.3                                          
276         1.5             84.3                                          
            6               84.3                                          
______________________________________                                    
 
    
     The herbicidal action of compounds of the formula I is demonstrated in greenhouse experiments. 
     The vessels employed were plastic flowerpots having a volume of 300 cm 3 , and which were filled with a sandy loam containing about 1.5% humus. The seeds of the test plants were sown shallow, and separately, according to species. For the preemergence treatment, the active ingredients were applied to the surface of the soil immediately after the seeds had been sown. The compounds were emulsified or suspended in water as vehicle, and sprayed through finely distributing nozzles. The application rates were 3.0 and 1.0 kg of active ingredient per hectare. After the agents had been applied, the vessels were lightly sprinkler-irrigated to induce germination an growth. Transparent plastic covers were then placed on the vessels until the plants had taken root. The cover ensured uniform germination of the plants, insofar as this was not impaired by the active ingredients. 
     For the postemergence treatment, the plants were first grown in the vessels to a height of from 3 to 15 cm, depending on growth form, before being treated. The soybean and rice plants were grown in a peat-enriched substrate. For this treatment, either plants which had been sown directly in the pots and grown there were selected, or plants which had been grown from seedlings and were transplanted to the pots a few days before treatment. The application rate for postemergence treatment was for example 1.0 kg of active ingredient per hectare. 
     The pots were set up in the greenhouse--species from warmer areas at from 20° to 30° C., and species from moderate climates at 15° to 25° C. The experiments were run for 2 to 4 weeks. During this period, the plants were tended and their reactions to the various treatments assessed. The scale used for assessment was 0 to 100, 0 denoting no damage or normal emergence, and 100 denoting nonemergence or complete destruction of at least the visible plant parts. 
     The plants used in the experiments were Amaranthus spp., Centaurea cyanus, Chenopodium album, Echinochloa, crus-galli, Galeopsis spp., Gaalium aparine, Glycine max., Ipomoea spp., Lamium amplexicaule, Lolium multiflorum, Lycopersicon lycopersicum, Mercurialis annua, Stellaria media, Triticum aestivum, Viola spp., and Zea mays. 
     At an application rate of 3.0 kg/ha, compounds nos. 131, 153, 166 and 192 had a considerable herbicidal action on broadleaved and grassy plants (postemergence application). 
     Compound no. 166, applied postemergence at a rate of 0.5 kg/ha, and compounds nos. 133, 142, 143, 150 and 167 at 1.0 kg/ha are suitable for selectively combatting unwanted plants in crops. Compounds nos. 166 and 204 combatted broadleaved weeds at a rate of 2.0 kg/ha. 
     
                                           TABLE 3                                 
__________________________________________________________________________
Selective control of broadleaved unwanted plants                          
in wheat on postemergence application in the                              
greenhouse                                                                
Com-    Test plants and % damage                                          
pound   Triticum*                                                         
               Galeopsis                                                  
                    Lamium                                                
                          Mercurialis                                     
                                Stellaria                                 
no. kg/ha                                                                 
        aestivum                                                          
               spp. ampl. annua media                                     
__________________________________________________________________________
166 2.0 0      100  100   100   100                                       
204 2.0 0      100  100    98   100                                       
__________________________________________________________________________
 &#34;Vuka&#34; variety