Abstract:
An insecticidal compound of the formula ##STR1## wherein A completes a 5 or 6 membered aromatic ring selected from the group pyridyl, pyridyl substituted with C 1-5  alkyl, C 1-5  haloalkyl, C 1-5  alkoxy, C 1-5  alkylthio, C 1-5  alkylsulfonyl, cyano, halogen, phenoxy or C 1-5  dialkylamino, pyrazinyl, pyrazinyl substituted with C 1-5  alkyl or halogen, pyrazolyl substitited with C 1-5  alkyl, pyridazyl substituted with halogen, or thiazolyl substituted with halogen or C 1-5  alkyl; 
     R 1  is hydrogen or C 1-5  alkyl, C 1-5  haloalkyl, C 1-5  alkoxy, C 1-5  alkylthio, C 1-5  alkylsulfonyl, cyano, halogen, phenoxy, or C 1-5  dialkylamino; 
     X is substituted or unsubstituted C 1-3  alkylene or C 1-3  alkylidene; 
     R 2  is hydrogen, monoalkylcarbamoyl, C 1-5  dialkylcarbamoyl, C 1-5  alkoyl, C 1-5  alkyl substituted with halogen, C 1-5  alkoxy, C 1-5  alkylthio, C 1-5  alkoxycarbonyl, cyano, aryl, haloaryl, C 1-5  alkoxyaryl, furyl, thienyl, pyridyl, halopyridyl, thiazolyl or halothiazolyl, C 2-5  alkyenyl, C 2-5  alkynyl, C 3-6  cycloalkyl, aryl, or the radical 
     
       --Y--R.sub.5 
     
     and an insecticidal acceptable salt thereof.

Description:
This is a continuation of application Ser. No. 07/700,165 filed on Jul. 9, 1991 now U.S. Pat. No. 5,304,566. 
    
    
     DESCRIPTION OF RELATED ART 
     The present invention relates to new amine derivatives, the processes for the production thereof and insecticides containing the said derivatives as effective compounds. 
     BACKGROUND ART 
     A large number of chemicals, for example, organophosphorus compounds such as parathion and malathion and carbamate compounds such as carbaryl and methomyl, have been developed and put to practical use as insecticides over many years. These insecticides have played a very great role for the improvement of agricultural production. However, in recent years some of these insecticides are regulated on their use because of problems such as environmental pollution due to residue or accumulation, or cause infestation of resistant insect pests as a result of long-term use. Therefore, there is a need to develop new chemicals which have excellent insecticidal characteristics over various types of insect pests including these resistant insect pests and which can be used safely. 
     The following compound is known as the isomer compound of this invention, which has no insecticidal activity. 
     
         TABLE 1  - Structure Formula  ##STR2##                                                                     C ompound No. R.sub.1 X R.sub.2 R.sub.3 Z R.sub.4 Physical Properties [ ] m.p. °C.  1 ##STR3##  H H N CN [123-126]  2 &#34; &#34; CH.sub.3 &#34; &#34; [141-143]   3 &#34; &#34; CH.sub.2  Cl &#34; &#34; [124-126]                                          4 &#34; &#34; CH.sub.2  F &#34; &#34; [151-152]                                                   5 &#34; &#34; CF.sub.3 &#34; &#34; [112-114]   6 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34; [120-122]                                      7 &#34; &#34; C.sub.3 H.sub.7  (n) &#34; &#34; [100-101]  8 &#34; &#34; ##STR4##  &#34; &#34; [193.5-195]              9 &#34; &#34; C.sub.4 H.sub.9  (t) &#34; &#34;                            10 &#34; &#34; CH.sub.2 OCH.sub.3 &#34; &#34; [128-128.5]   11 &#34; &#34; CH.sub.2  SCH.sub.3 &#34; &#34; [116-118]  12 ##STR5##  &#34; CH.sub.2 COOC.sub.2 H.sub.5 N CN n.sub.D  .sup.25.5 1.5608                                        13 &#34; &#34; CH.sub.2 CH.sub.2 COOC.sub.2  H.sub.5 &#34; &#34;                                                     14 &#34; &#34; CH.sub.2  NHCH.sub.3 &#34; &#34;                                                    15 &#34; &#34; CH.sub.2  N(CH.sub.3).sub.2 &#34; &#34;                                           16 &#34; &#34; CH.sub.2 CH.sub.2 CH.sub.2  Cl &#34; &#34; [114-115]  17 &#34; &#34; ##STR6##  &#34; &#34; [190-191]  18 &#34; &#34; CH.sub.2  CN &#34; &#34; [106-108]                                          19 &#34; &#34; CH.sub.2 CH.sub.2  CN &#34; &#34;  20 &#34; &#34; ##STR7##  &#34; &#34; [187-189]  21 &#34; CH.sub.3 H &#34; &#34; n.sub.D  .sup.25 1.5918                                22 &#34; &#34; CH.sub.3 &#34; &#34; [101-103]  23 &#34; &#34; &#34; &#34; &#34; [161-162]  HCl salt   24 &#34; &#34; CH.sub.2 Cl &#34; &#34; n.sub.D  .sup.26.5 1.5921                          25 &#34; &#34; CH.sub.2 F &#34; &#34; [79-80]  26 &#34; &#34; CF.sub.3 &#34; &#34; *1  27 ##STR8##  CH.sub.3 C.sub.2 H.sub.5 N CN n.sub.D  .sup.27 1.5742                                   28 &#34; &#34; C.sub.3 H.sub.7 (n) &#34; &#34; [97-100]  29 &#34; &#34; ##STR9##  &#34; &#34; n.sub.D  .sup.24.5 1.5829         30 &#34; &#34; C.sub.4 H.sub.9  (t) &#34; &#34;                                31 &#34; &#34; CH.sub.2 OCH.sub.3 &#34; &#34; n.sub.D  .sup.24 1.5803                                                     32 &#34; &#34; CH.sub.2 SCH.sub.3 &#34; &#34; n.sub.D  .sup.24.5 1.6070                          33 &#34; &#34; CH.sub.2 COOC.sub.2 H.sub.5 &#34; &#34; n.sub.D  .sup.25.5 1.5604                                       34 &#34; &#34; CH.sub.2 CH.sub.2 COOC.sub.2 H.sub.5 &#34; &#34; n.sub.D  .sup.24.5 1.5605                   35 &#34; &#34; CH.sub.2 NHCH.sub.3 &#34; &#34; n.sub.D  .sup.25 1.5861                                                     36 &#34; &#34; CH.sub.2 N(CH.sub.3).sub.2 &#34; &#34; n.sub.D  .sup.25 1.5577                    37 &#34; &#34; CH.sub.2 CH.sub.2 Cl &#34; &#34;    38 &#34; &#34; CH.sub.2 CH.sub.2 CH.sub.2 Cl &#34; &#34; n.sub.D .sup.25.5 1.5830  39 &#34; &#34; ##STR10##  &#34; &#34;  40 &#34; &#34; ##STR11##  &#34; &#34;  41 &#34; &#34; ##STR12##  &#34; &#34; n.sub.D  .sup.25.5 1.6040  42 ##STR13##  CH.sub.3 CHCH.sub.2   N CN                 43 &#34; &#34; CH.sub.2 CN &#34; &#34; n.sub.D .sup.25 1.5913    44 &#34; &#34; CH.sub.2 CH.sub.2  CN &#34; &#34; [112-114]  45 &#34; &#34; ##STR14##  &#34; &#34;  46 &#34; &#34; ##STR15##  &#34; &#34; [224-226]  47 &#34; CHF.sub.2 H &#34; &#34;   48 &#34; &#34; CH.sub.3 &#34; &#34; n.sub.D  .sup.24.5 1.5423                             49 &#34; &#34; C.sub.2 H.sub.5 &#34; &#34;   50 &#34; C.sub.2  H.sub.5 H &#34; &#34; [101-103]                                     51 &#34; &#34; CH.sub.3 &#34; &#34; [100-101]   52 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                               53 &#34; C.sub.3 H.sub.7  (i) H &#34; &#34; [205-207]                                                54 &#34; &#34; CH.sub.3 &#34; &#34;   55 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;  56 &#34; ##STR16##  H &#34; &#34;  57 ##STR17##  ##STR18##  CH.sub.3 N CN n.sub.D  .sup.25 1.5825                   58 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                          59 &#34; CH.sub.2 OCH.sub.3 H &#34; &#34;   60 &#34; &#34; CH.sub.3 &#34; &#34; n.sub.D  .sup.25.5 1.5711                        61 &#34; CH.sub.2 SCH.sub.3 H &#34; &#34;62 &#34; &#34; CH.sub.3 &#34; &#34; n.sub.D  .sup.25 1.5828                             63 &#34; CH.sub.2 COOC.sub.2 H.sub.5 H &#34; &#34;   64 &#34; &#34; CH.sub.3 &#34; &#34; n.sub.D  .sup.25 1.5475  65 &#34; ##STR19##  H &#34; &#34;  66 &#34; &#34; CH.sub.3 &#34; &#34; n.sub.D  .sup.25.5 1.5928  67 &#34; ##STR20##  H &#34; &#34;  68 &#34; &#34; CH.sub.3 &#34; &#34; n.sub.D  .sup.25.5 1.6155  69 &#34; ##STR21##  H &#34; &#34;  70 &#34; &#34; CH.sub.3 &#34; &#34; n.sub.D  .sup.24.5 1.6093  71 &#34; ##STR22##  H &#34; &#34;  72 ##STR23##  ##STR24##  CH.sub.3 N CN [112-114]  73 &#34; CH.sub.2 CHCH.sub.2  H &#34; &#34; n.sub.D  .sup.25 1.5841                    74 &#34; &#34; CH.sub.3 &#34; &#34; n.sub.D .sup.25 1.5809   75 &#34; CH.sub.2  CCH H &#34; &#34;                                                  76 &#34; &#34; CH.sub.3 &#34; &#34; n.sub.D  .sup.25.5 1.5730                                      77 &#34; CH.sub.2 CN H &#34; &#34;  78 &#34; &#34; CH.sub.3 &#34; &#34; [127-128]  79 &#34; ##STR25##  H &#34; &#34;  80 &#34; &#34; CH.sub.3 &#34; &#34; [124-127]  81 &#34; ##STR26##  H &#34; &#34;  82 &#34; &#34; CH.sub.3 &#34; &#34; n.sub.D  .sup.24.5 1.6045  83 &#34; ##STR27##  H &#34; &#34;  84 &#34; &#34; CH.sub.3 &#34; &#34; n.sub.D  .sup.25.5 1.6092  85 &#34; ##STR28##  H &#34; &#34;  86 ##STR29##  ##STR30##  CH.sub.3 N CN n.sub.D  .sup.25.5 1.5910  87 &#34; ##STR31##  H &#34; &#34;  88 &#34; &#34; CH.sub.3 &#34; &#34; n.sub.D  .sup.25.5 1.6162  89 &#34; ##STR32##  H &#34; &#34;  90 &#34; &#34; CH.sub.3 &#34; &#34; [115-117]  91 &#34; OCH.sub.3 H &#34; &#34;  92 &#34; &#34; CH.sub.3 &#34; &#34; [110-112]  93 &#34; CHO H &#34; &#34;  94 &#34; &#34; CH.sub.3 &#34; &#34;   95 &#34; COCH.sub.3 H &#34; &#34; n.sub.D  .sup.25.5 1.5475                           96 &#34; &#34; CH.sub.3 &#34; &#34; [84-86]    97 &#34; SO.sub.2  CH.sub.3 H &#34; &#34; [160-163]                                  98 &#34; &#34; CH.sub.3 &#34; &#34;  99 &#34; ##STR33##  H &#34; &#34; 100 &#34; &#34; CH.sub.3 &#34; &#34; [112-114] 101  ##STR34##  COOC.sub.2  H.sub.5 H N CN       102 &#34; &#34; CH.sub.3 &#34; &#34; n.sub.D  .sup.25 1.5540                    103 &#34; CONH.sub.2 H &#34; &#34;  104 &#34; &#34; CH.sub.3 &#34; &#34; 105 &#34;  ##STR35##  H &#34; &#34; 106 &#34; &#34; CH.sub.3 &#34; &#34; [89-91]  107 &#34; CONHCH.sub.3 H &#34; &#34;  108 &#34; &#34; CH.sub.3 &#34; &#34;  109 &#34; CSNHCH.sub.3 H &#34; &#34;  110 &#34; &#34; CH.sub.3 &#34; &#34; 111  ##STR36##  H CH.sub.3 &#34; &#34; 112 &#34; CH.sub.3 &#34; &#34; &#34; 113  ##STR37##  H &#34; &#34; &#34; 114 &#34; CH.sub.3 &#34; &#34; &#34; 115  ##STR38##  H &#34; &#34; &#34; [83-85] 116  ##STR39##  CH.sub.3 CH.sub.3 N CN [76-78] 117  ##STR40##  H &#34; &#34; &#34; 118 &#34; CH.sub.3 &#34; &#34; &#34; [145-147] 119  ##STR41##  H &#34; &#34; &#34; 120 &#34; CH.sub.3 &#34; &#34; &#34; n.sub.D  .sup.25 1.5202                        121  ##STR42##  H &#34; &#34; &#34; 122 &#34; CH.sub.3 &#34; &#34; &#34; 123  ##STR43##  H &#34; &#34; &#34; 124 &#34; CH.sub.3 &#34; &#34; &#34; n.sub.D  .sup.25.5 1.5580                        125  ##STR44##  H &#34; &#34; &#34; 126 &#34; CH.sub.3 &#34; &#34; &#34; 127  ##STR45##  H &#34; &#34; &#34; 128 &#34; CH.sub.3 &#34; &#34; &#34; 129  ##STR46##  H &#34; &#34; &#34; [162-163] 130 &#34; CH.sub.3 &#34; &#34; &#34; [105-107] 131  ##STR47##  H CH.sub.3 N CN 132 &#34; CH.sub.3 &#34; &#34; &#34; [138-139] 133  ##STR48##  H &#34; &#34; &#34; 134 &#34; CH.sub.3 &#34; &#34; &#34; n.sub.D  .sup.25 1.5841                        135  ##STR49##  H &#34; &#34; &#34; 136 &#34; CH.sub.3 &#34; &#34; &#34; [107-109] 137  ##STR50##  H &#34; &#34; &#34; 138 &#34; CH.sub.3 &#34; &#34; &#34; 139  ##STR51##  H &#34; &#34; &#34; 140 &#34; CH.sub.3 &#34; &#34; &#34; 141  ##STR52##  H &#34; &#34; &#34; 142 &#34; CH.sub.3 &#34; &#34; &#34; 143  ##STR53##  H &#34; &#34; &#34; [122-124] 144 &#34; CH.sub.3 &#34; &#34; &#34; [110-113] 145  ##STR54##  H CH.sub.3 N CN [66-68] 146 &#34; CH.sub.3 &#34; &#34; &#34; n.sub.D  .sup.24.5 1.5790                        147  ##STR55##  H &#34; &#34; &#34; 148 &#34; CH.sub.3 &#34; &#34; &#34; [94-96] 149  ##STR56##  H &#34; &#34; &#34; [130-132] 150 &#34; CH.sub.3 &#34; &#34; &#34; n.sub.D  .sup.25 1.5612                        151  ##STR57##  H &#34; &#34; &#34; [96-99] 152 &#34; CH.sub.3 &#34; &#34; &#34; n.sub.D  .sup.25.5 1.5800                        153  ##STR58##  H &#34; &#34; &#34; 154 &#34; CH.sub.3 &#34; &#34; &#34; 155  ##STR59##  H &#34; &#34; &#34; 156  ##STR60##  CH.sub.3 CH.sub.3 N CN 157  ##STR61##  H &#34; &#34; &#34; 158 &#34; CH.sub.3 &#34; &#34; &#34; 159  ##STR62##  H &#34; &#34; &#34; 160 &#34; CH.sub.3 &#34; &#34; &#34; 161  ##STR63##  H &#34; &#34; &#34; 162 &#34; CH.sub.3 &#34; &#34; &#34; 163  ##STR64##  H &#34; &#34; &#34; [115-117] 164 &#34; CH.sub.3 &#34; &#34; &#34; n.sub.D  .sup.23 1.5717                        165  ##STR65##  H &#34; &#34; &#34; [104-106] 166 &#34; CH.sub.3 &#34; &#34; &#34; 167  ##STR66##  H CH.sub.3 N CN 168 &#34; CH.sub.3 &#34; &#34; &#34; 169  ##STR67##  H &#34; &#34; &#34; [112-114] 170 &#34; CH.sub.3 &#34; &#34; &#34; n.sub.D  .sup.25 1.5413                        171  ##STR68##  H &#34; &#34; &#34; [122-124] 172 &#34; CH.sub.3 &#34; &#34; &#34; [143-144]  173 &#34; &#34; C.sub.2 H.sub.5 &#34; &#34; n.sub.D  .sup.25 1.5575                       174 &#34; C.sub.2 H.sub.5 CH.sub.3 &#34; &#34; [63-70] 175  ##STR69##  H &#34; &#34; &#34; [149-151] 176 &#34; CH.sub.3 &#34; &#34; &#34; 177  ##STR70##  H H &#34; &#34; [179-183] 178 &#34; CH.sub.3 &#34; &#34; &#34; n.sub.D  .sup.25 1.5952                        179  ##STR71##  H CH.sub.3 N CN 180 &#34; CH.sub.3 &#34; &#34; &#34; 181  ##STR72##  H &#34; &#34; &#34; 182 &#34; CH.sub.3 &#34; &#34; &#34; 183  ##STR73##  H &#34; &#34; &#34; 184 &#34; CH.sub.3 &#34; &#34; &#34; 185  ##STR74##  H &#34; &#34; &#34; 186 &#34; CH.sub.3 &#34; &#34; &#34; 187  ##STR75##  H &#34; &#34; &#34; 188 &#34; CH.sub.3 &#34; &#34; &#34; [106-109] 189  ##STR76##  H CH.sub.3 &#34; &#34; [90-92] 190  ##STR77##  CH.sub.3 CH.sub.3 N CN [102-103] 191  ##STR78##  H &#34; &#34; &#34; 192 &#34; CH.sub.3 &#34; &#34; &#34; 193  ##STR79##  H H &#34; &#34; 194 &#34; &#34; CH.sub.3 &#34; &#34; [127-129]  195 &#34; &#34; CH.sub.2  Cl &#34; &#34;                                                  196 &#34; &#34; CH.sub.2  F &#34; &#34;                                                            197 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;    198 &#34; &#34;  ##STR80##  &#34; &#34; 199 &#34; &#34; CH.sub.2  SCH.sub.3 &#34; &#34;                                            200 &#34; &#34; CH.sub.2  OCH.sub.3 &#34; &#34;   201  ##STR81##  H C.sub.3 H.sub.7 (n) N CN n.sub.D  .sup.25.5 1.5528                               202 &#34; CH.sub.3 H &#34; &#34;  203 &#34; &#34; CH.sub.3 &#34; &#34; n.sub.D  .sup.25.5 1.5798                            204 &#34; &#34; CH.sub.2 Cl &#34; &#34; 205 &#34; &#34; CH.sub.2  F &#34; &#34;                                               206 &#34; H C.sub.2 H.sub.5 &#34; &#34; n.sub.D  .sup.25.5 1.5657               207 &#34; &#34;  ##STR82##  &#34; &#34; 208 &#34; &#34; CH.sub.2  SCH.sub.3 &#34; &#34;                                            209 &#34; &#34; CH.sub.2  OCH.sub.3 &#34; &#34;                                                    210 &#34; &#34; C.sub.3 H.sub.7  (i) &#34; &#34;                                                 211 &#34; &#34; C.sub.4 H.sub.9  (t) &#34; &#34;  212  ##STR83##  C.sub.2  H.sub.5 H N CN   213 &#34; &#34; CH.sub.3 &#34; &#34; n.sub.D  .sup.24.5 1.5665                      214 &#34; &#34; CH.sub.2  Cl &#34; &#34;            215 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                            216 &#34; C.sub.3 H.sub.7 (i) H &#34; &#34;   217 &#34; &#34; CH.sub.3 &#34; &#34;  218 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              219 &#34; COCH.sub. 3 H &#34; &#34;  220 &#34; &#34; CH.sub.3 &#34; &#34;  221 &#34; SO.sub.2  CH.sub.3 H &#34; &#34;                                            222 &#34; &#34; CH.sub.3 &#34; &#34; 223  ##STR84##  H H N NO.sub.2 224 &#34; &#34; CH.sub.3 &#34; &#34;  225 &#34; &#34; CH.sub.2  Cl &#34; &#34;                                                  226 &#34; &#34; CH.sub.2  F &#34; &#34;                                                            227 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;    228 &#34; &#34;  ##STR85##  &#34; &#34; 229 &#34; &#34; CH.sub.2  SCH.sub.3 &#34; &#34;                                            230 &#34; &#34; CH.sub.2  OCH.sub.3 &#34; &#34;                                                    231 &#34; &#34; C.sub.3 H.sub.7  (i) &#34; &#34;                                                 232 &#34; &#34; C.sub.4 H.sub.9  (t) &#34; &#34;                                                           233 &#34; &#34; CHCH.sub.2   &#34; &#34;        234 &#34; &#34;  ##STR86##  &#34; &#34; 235  ##STR87##  CH.sub.3 H N NO.sub.2 236 &#34; &#34; CH.sub.3 &#34; &#34; n.sub.D  .sup.25 1.5808                               237 &#34; &#34; CH.sub.2 Cl &#34; &#34;238 &#34; &#34; CH.sub.2  F &#34; &#34;                                                239 &#34; &#34; C.sub.2 H.sub.5 &#34; &#34; 240 &#34; &#34;  ##STR88##  &#34; &#34; 241 &#34; &#34; CH.sub.2  SCH.sub.3 &#34; &#34;                                            242 &#34; &#34; CH.sub.2  OCH.sub.3 &#34; &#34;                                                    243 &#34; &#34; C.sub.3 H.sub.7  (n) &#34; &#34;                                                 244 &#34; &#34; C.sub.4 H.sub.9  (t) &#34; &#34;                                                           245 &#34; &#34; CHCH.sub.2   &#34; &#34;        246 &#34; &#34;  ##STR89##  &#34; &#34; 247  ##STR90##  C.sub.2  H.sub.5 H N NO.sub.2   248 &#34; &#34; CH.sub.3 &#34; &#34;  249 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              250 &#34; C.sub.3 H.sub.7  (i) H &#34; &#34;                                                         251 &#34; &#34; CH.sub.3 &#34; &#34;  252 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;            253 &#34;  ##STR91##  H &#34; &#34; 254 &#34; &#34; CH.sub.3 &#34; &#34;  255 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              256 &#34; COCH.sub. 3 H &#34; &#34;  257 &#34; &#34; CH.sub.3 &#34; &#34;  258 &#34; SO.sub.2  CH.sub.3 H &#34; &#34;                                            259 &#34; &#34; CH.sub.3 &#34; &#34; 260  ##STR92##  H CH.sub.3 N NO.sub.2 261 &#34; CH.sub.3 &#34; &#34; &#34; 262  ##STR93##  H &#34; &#34; &#34; 263 &#34; CH.sub.3 &#34; &#34; &#34; 264  ##STR94##  H &#34; &#34; &#34; 265 &#34; CH.sub.3 &#34; &#34; &#34; 266  ##STR95##  H &#34; &#34; &#34; 267 &#34; CH.sub.3 &#34; &#34; &#34; 268  ##STR96##  H &#34; &#34; &#34; 269 &#34; CH.sub.3 &#34; &#34; &#34; 270  ##STR97##  H &#34; &#34; &#34; 271 &#34; CH.sub.3 &#34; &#34; &#34; 272  ##STR98##  H CH.sub.3 N NO.sub.2 273 &#34; CH.sub.3 &#34; &#34; &#34; 274  ##STR99##  H &#34; &#34; &#34; 275 &#34; CH.sub.3 &#34; &#34; &#34; 276  ##STR100##  H &#34; &#34; &#34; 277 &#34; CH.sub.3 &#34; &#34; &#34; 278  ##STR101##  H &#34; &#34; &#34; 279 &#34; CH.sub.3 &#34; &#34; &#34; 280  ##STR102##  H &#34; &#34; &#34; 281 &#34; CH.sub.3 &#34; &#34; &#34; 282  ##STR103##  H &#34; &#34; &#34; 283 &#34; CH.sub.3 &#34; &#34; &#34; 284  ##STR104##  H CH.sub.3 N NO.sub.2 285 &#34; CH.sub.3 &#34; &#34; &#34; 286  ##STR105##  H &#34; &#34; &#34; 287 &#34; CH.sub.3 &#34; &#34; &#34; 288  ##STR106##  H &#34; &#34; &#34; 289 &#34; CH.sub.3 &#34; &#34; &#34; 290  ##STR107##  H &#34; &#34; &#34; 291 &#34; CH.sub.3 &#34; &#34; &#34; 292  ##STR108##  H &#34; &#34; &#34; 293 &#34; CH.sub.3 &#34; &#34; &#34; 294  ##STR109##  H CH.sub.3 N NO.sub.2 295 &#34; CH.sub.3 &#34; &#34; &#34; 296  ##STR110##  H &#34; &#34; &#34; 297 &#34; CH.sub.3 &#34; &#34; &#34; 298  ##STR111##  H &#34; &#34; &#34; 299 &#34; CH.sub.3 &#34; &#34; &#34; 300  ##STR112##  H &#34; &#34; &#34; 301 &#34; CH.sub.3 &#34; &#34; &#34; 302  ##STR113##  H &#34; &#34; &#34; 303 &#34; CH.sub.3 &#34; &#34; &#34; 304  ##STR114##  H &#34; &#34; &#34; 305  ##STR115##  CH.sub.3 CH.sub.3 N NO.sub.2 306  ##STR116##  H &#34; &#34; &#34; 307 &#34; CH.sub.3 &#34; &#34; &#34; 308  ##STR117##  H &#34; &#34; &#34; 309 &#34; CH.sub.3 &#34; &#34; &#34; 310  ##STR118##  H &#34; &#34; &#34; 311 &#34; CH.sub.3 &#34; &#34; &#34; 312  ##STR119##  H &#34; &#34; &#34; 313 &#34; CH.sub.3 &#34; &#34; &#34; 314  ##STR120##  H CH.sub.3 N NO.sub.2 315 &#34; CH.sub.3 &#34; &#34; &#34; 316  ##STR121##  H &#34; &#34; &#34; 317 &#34; CH.sub.3 &#34; &#34; &#34; 318  ##STR122##  H &#34; &#34; &#34; 319 &#34; CH.sub.3 &#34; &#34; &#34;  320 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              321 &#34; C.sub.2 H.sub.5 CH.sub.3 &#34; &#34; 322  ##STR123##  H &#34; &#34; &#34; 323 &#34; CH.sub.3 &#34; &#34; &#34; 324  ##STR124##  H CH.sub.3 N NO.sub.2 325 &#34; CH.sub.3 &#34; &#34; &#34; 326  ##STR125##  H &#34; &#34; &#34; 327 &#34; CH.sub.3 &#34; &#34; &#34; 328  ##STR126##  H &#34; &#34; &#34; 329 &#34; CH.sub.3 &#34; &#34; &#34; 330  ##STR127##  H &#34; &#34; &#34; 331 &#34; CH.sub.3 &#34; &#34; &#34; 332  ##STR128##  H &#34; &#34; &#34; 333 &#34; CH.sub.3 &#34; &#34; &#34; 334  ##STR129##  H &#34; &#34; &#34; 335 &#34; CH.sub.3 &#34; &#34; &#34; 336  ##STR130##  H H N NO.sub.2 337 &#34; &#34; CH.sub.3 &#34; &#34;  338 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              339 &#34; &#34; CH.sub.2  Cl &#34; &#34;                                                           340 &#34; &#34; CH.sub.2  F &#34; &#34;     341 &#34; &#34;  ##STR131##  &#34; &#34; 342 &#34; &#34; CH.sub.2  SCH.sub.3 &#34; &#34;                                            343 &#34; &#34; CH.sub.2  OCH.sub.3 &#34; &#34;   344  ##STR132##  CH.sub.3 H N NO.sub.2 345 &#34; &#34; CH.sub.3 &#34; &#34;  346 &#34; &#34; CH.sub.2  Cl &#34; &#34;                                                  347 &#34; &#34; CH.sub.2  F &#34; &#34;                                                            348 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;    349 &#34; &#34;  ##STR133##  &#34; &#34; 350 &#34; &#34; CH.sub.2  SCH.sub.3 &#34; &#34;                                            351 &#34; &#34; CH.sub.2  OCH.sub.3 &#34; &#34;                                                    352 &#34; &#34; C.sub.3 H.sub.7  (i) &#34; &#34;                                                 353 &#34; &#34; C.sub.4 H.sub.9  (t) &#34; &#34;  354  ##STR134##  C.sub.2  H.sub.5 H N NO.sub.2   355 &#34; &#34; CH.sub.3 &#34; &#34;  356 &#34; &#34; CH.sub.2  Cl &#34; &#34;                                                  357 &#34; &#34; C.sub.2 H.sub.5 &#34; &#34;  358 &#34; C.sub.3 H.sub.7  (i) H &#34; &#34;                                          359 &#34; &#34; CH.sub.3 &#34; &#34;  360 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              361 &#34; COCH.sub. 3 H &#34; &#34;  362 &#34; &#34; CH.sub.3 &#34; &#34;  363 &#34; SO.sub.2  CH.sub.3 H &#34; &#34;                                            364 &#34; &#34; CH.sub.3 &#34; &#34; 365  ##STR135##  H H CH NO.sub.2 [116-118] 366 &#34; &#34; CH.sub.3 &#34; &#34; [133-135]  367 &#34; &#34; CH.sub.2  Cl &#34; &#34;                                                  368 &#34; &#34; C.sub.2 H.sub.5 &#34; &#34; [95-98]  369 &#34; &#34; C.sub.3 H.sub.7  (i) &#34; &#34; [150-152]                                370 &#34; &#34; C.sub.4 H.sub.7  (t) &#34; &#34;                                                           371 &#34; &#34; CHCH.sub.2   &#34; &#34;                                                         372 &#34; &#34; CHCHCH.sub.3 &#34; &#34;  373 &#34; &#34; CH.sub.2  CN &#34; &#34;                                                  374 &#34; &#34; CH.sub.2  NO.sub.2 &#34; &#34;                                                     375 &#34; &#34; CH.sub.2 COOC.sub.2  H.sub.5 &#34; &#34;                 376  ##STR136##  H  ##STR137##  CH NO.sub.2 377 &#34; &#34;  ##STR138##  &#34; &#34; 378 &#34; &#34;  ##STR139##  &#34; &#34; 379 &#34; &#34;  ##STR140##  &#34; &#34; 380 &#34; CH.sub.3 H &#34; &#34;  381 &#34; &#34; CH.sub.3 &#34; &#34; [79-82]  382 &#34; &#34; CH.sub.2  Cl &#34; &#34;                                                  383 &#34; &#34; C.sub.2 H.sub.5 &#34; &#34; [101-104]  384 &#34; &#34; C.sub.3 H.sub.7  (i) &#34; &#34;                                          385 &#34; &#34; C.sub.4 H.sub.7  (t) &#34; &#34;                                                           386 &#34; &#34; CHCH.sub.2   &#34; &#34;                                                         387 &#34; &#34; CHCHCH.sub.3 &#34; &#34; 388  ##STR141##  CH.sub.3 CH.sub.2  CN CH NO.sub.2              389 &#34; &#34; CH.sub.2  NO.sub.2 &#34; &#34;                           390 &#34; &#34; CH.sub.2 COOC.sub.2 H.sub.5 &#34; &#34; 391 &#34; &#34;  ##STR142##  &#34; &#34; 392 &#34; &#34;  ##STR143##  &#34; &#34; 393 &#34; &#34;  ##STR144##  &#34; &#34; 394 &#34; &#34;  ##STR145##  &#34; &#34; 395 &#34; C.sub.2  H.sub.5 H &#34; &#34;                                               396 &#34; &#34; CH.sub.3 &#34; &#34;  397 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              398 &#34; C.sub.3 H.sub.7  (i) H &#34; &#34;                                                         399 &#34; &#34; CH.sub.3 &#34; &#34; 400  ##STR146##  C.sub.3 H.sub.7 (i) C.sub.2  H.sub.5 CH NO.sub.2                        401 &#34;  ##STR147##  H &#34; &#34; 402 &#34; &#34; CH.sub.3 &#34; &#34;  403 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              404 &#34; CH.sub.2 CHCH.sub.2   H &#34; &#34;                                                         405 &#34; &#34; CH.sub.3 &#34; &#34;  406 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;            407 &#34;  ##STR148##  H &#34; &#34; 408 &#34; &#34; CH.sub.3 &#34; &#34;  409 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              410 &#34; CHO H &#34; &#34;  411 &#34; &#34; CH.sub.3 &#34; &#34; 412  ##STR149##  CHO C.sub.2  H.sub.5 CH NO.sub.2        413 &#34; COCH.sub.3 H &#34; &#34;  414 &#34; &#34; CH.sub.3 &#34; &#34;  415 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              416 &#34; SO.sub.2 CH.sub.3 H &#34; &#34;  417 &#34; &#34; CH.sub.3 &#34; &#34;  418 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              419 &#34; COOC.sub. 2  H.sub.5 H &#34; &#34; 420 &#34; &#34; CH.sub.3 &#34; &#34;  421 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              422 &#34; OC.sub.2 H.sub.5 H &#34; &#34;  423 &#34; &#34; CH.sub.3 &#34; &#34;  424 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              425 &#34; CH.sub.2 CCH H &#34; &#34;  426 &#34; &#34; CH.sub.3 &#34; &#34;  427 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;            428  ##STR150##  H CH.sub.3 CH NO.sub.2 429 &#34; CH.sub.3 &#34; &#34; &#34; 430  ##STR151##  H &#34; &#34; &#34; 431 &#34; CH.sub.3 &#34; &#34; &#34; 432  ##STR152##  H &#34; &#34; &#34; 433 &#34; CH.sub.3 &#34; &#34; &#34; 434  ##STR153##  H &#34; &#34; &#34; 435 &#34; CH.sub.3 &#34; &#34; &#34; 436  ##STR154##  H &#34; &#34; &#34; 437 &#34; CH.sub.3 &#34; &#34; &#34; 438  ##STR155##  H &#34; &#34; &#34; 439 &#34; CH.sub.3 &#34; &#34; &#34; 440  ##STR156##  H CH.sub.3 CH NO.sub.2 441 &#34; CH.sub.3 &#34; &#34; &#34; 442  ##STR157##  H &#34; &#34; &#34; 443 &#34; CH.sub.3 &#34; &#34; &#34; 444  ##STR158##  H &#34; &#34; &#34; 445 &#34; CH.sub.3 &#34; &#34; &#34; 446  ##STR159##  H &#34; &#34; &#34; 447 &#34; CH.sub.3 &#34; &#34; &#34; 448  ##STR160##  H &#34; &#34; &#34; 449 &#34; CH.sub.3 &#34; &#34; &#34; 450  ##STR161##  H &#34; &#34; &#34; 451 &#34; CH.sub.3 &#34; &#34; &#34; 452  ##STR162##  H CH.sub.3 CH NO.sub.2 453 &#34; CH.sub.3 &#34; &#34; &#34; 454  ##STR163##  H &#34; &#34; &#34; 455 &#34; CH.sub.3 &#34; &#34; &#34; 456  ##STR164##  H &#34; &#34; &#34; 457 &#34; CH.sub.3 &#34; &#34; &#34; 458  ##STR165##  H &#34; &#34; &#34; 459 &#34; CH.sub.3 &#34; &#34; &#34; 460  ##STR166##  H &#34; &#34; &#34; 461 &#34; CH.sub.3 &#34; &#34; &#34; 462  ##STR167##  H CH.sub.3 CH NO.sub.2 463 &#34; CH.sub.3 &#34; &#34; &#34; 464  ##STR168##  H &#34; &#34; &#34; 465 &#34; CH.sub.3 &#34; &#34; &#34; 466  ##STR169##  H &#34; &#34; &#34; 467 &#34; CH.sub.3 &#34; &#34; &#34; 468  ##STR170##  H &#34; &#34; &#34; 469 &#34; CH.sub.3 &#34; &#34; &#34; 470  ##STR171##  H &#34; &#34; &#34; 471 &#34; CH.sub.3 &#34; &#34; &#34; 472  ##STR172##  H &#34; &#34; &#34; 473  ##STR173##  CH.sub.3 CH.sub.3 CH NO.sub.2 474  ##STR174##  H &#34; &#34; &#34; 475 &#34; CH.sub.3 &#34; &#34; &#34; 476  ##STR175##  H &#34; &#34; &#34; 477 &#34; CH.sub.3 &#34; &#34; &#34; 478  ##STR176##  H &#34; &#34; &#34; 479 &#34; CH.sub.3 &#34; &#34; &#34; 480  ##STR177##  H &#34; &#34; &#34; 481 &#34; CH.sub.3 &#34; &#34; &#34; 482  ##STR178##  H &#34; &#34; &#34; 483 &#34; CH.sub.3 &#34; &#34; &#34; 484  ##STR179##  H CH.sub.3 CH NO.sub.2 485 &#34; CH.sub.3 &#34; &#34; &#34; 486  ##STR180##  H &#34; &#34; &#34; 487 &#34; CH.sub.3 &#34; &#34; &#34;  488 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              489 &#34; C.sub.2 H.sub.5 CH.sub.3 &#34; &#34; 490  ##STR181##  H &#34; &#34; &#34; 491 &#34; CH.sub.3 &#34; &#34; &#34; 492  ##STR182##  H &#34; &#34; &#34; 493 &#34; CH.sub.3 &#34; &#34; &#34; 494  ##STR183##  H &#34; &#34; &#34; 495 &#34; CH.sub.3 &#34; &#34; &#34; 496  ##STR184##  H CH.sub.3 CH NO.sub.2 497 &#34; CH.sub.3 &#34; &#34; &#34; 498  ##STR185##  H &#34; &#34; &#34; 499 &#34; CH.sub.3 &#34; &#34; &#34; 500  ##STR186##  H &#34; &#34; &#34; 501 &#34; CH.sub.3 &#34; &#34; &#34; 502  ##STR187##  H H CH NO.sub.2 503 &#34; &#34; CH.sub.3 &#34; &#34;  504 &#34; &#34; CH.sub.2  Cl &#34; &#34;                                                  505 &#34; &#34; C.sub.2 H.sub.5 &#34; &#34;  506 &#34; &#34; C.sub.3 H.sub.7  (i) &#34; &#34;                                          507 &#34; &#34; C.sub.4 H.sub.9  (t) &#34; &#34;                                                           508 &#34; CH.sub.3 H &#34; &#34;  509 &#34; &#34; CH.sub.3 &#34; &#34;  510 &#34; &#34; CH.sub.2  Cl &#34; &#34;                                                  511 &#34; &#34; C.sub.2 H.sub.5 &#34; &#34; 512 &#34; &#34;  ##STR188##  &#34; &#34; 513  ##STR189##  CH.sub.3 C.sub.3 H.sub.7  (i) CH NO.sub.2                     514 &#34; &#34; C.sub.4 H.sub.9  (t) &#34; &#34;                  515 &#34; C.sub.2  H.sub.5 H &#34; &#34;                     516 &#34; &#34; CH.sub.3 &#34; &#34;  517 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;            518 &#34;  ##STR190##  H &#34; &#34; 519 &#34; &#34; CH.sub.3 &#34; &#34;  520 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              521 &#34; COCH.sub. 3 H &#34; &#34;  522 &#34; &#34; CH.sub.3 &#34; &#34;  523 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              524 &#34; SO.sub.2 CH.sub.3 H &#34; &#34;  525 &#34; &#34; CH.sub.3 &#34; &#34;  526 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;            527  ##STR191##  H H CH CN 528 &#34; &#34; CH.sub.3 &#34; &#34; [95-98]  529 &#34; &#34; CH.sub.2  Cl &#34; &#34;                                                  530 &#34; &#34; C.sub.2 H.sub.5 &#34; &#34;  531 &#34; &#34; C.sub.3 H.sub.7  (i) &#34; &#34;                                          532 &#34; &#34; C.sub.4 H.sub.9  (t) &#34; &#34;                                                           533 &#34; &#34; CHCH.sub.2   &#34; &#34;                                                         534 &#34; &#34; CHCHCH.sub.3 &#34; &#34;  535 &#34; &#34; CH.sub.2  CN &#34; &#34;                                                  536 &#34; &#34; CH.sub.2  NO.sub.2 &#34; &#34;                                                     537 &#34; &#34; CH.sub.2 COOC.sub.2  H.sub.5 &#34; &#34;                 538  ##STR192##  H  ##STR193##  CH CN 539 &#34; &#34;  ##STR194##  &#34; &#34; 540 &#34; &#34;  ##STR195##  &#34; &#34; 541 &#34; &#34;  ##STR196##  &#34; &#34; 542 &#34; CH.sub.3 H &#34; &#34;  543 &#34; &#34; CH.sub.3 &#34; &#34; n.sub.D  .sup.29 1.5941                              544 &#34; &#34; CH.sub.2 Cl &#34; &#34; 545 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                          546 &#34; &#34; C.sub.3 H.sub.7  (i) &#34; &#34;                                                           547 &#34; &#34; C.sub.4 H.sub.9  (t) &#34; &#34;                                                 548 &#34; &#34; CHCH.sub.2   &#34; &#34;                                                           549 &#34; &#34; CHCHCH.sub.3 &#34; &#34; 550  ##STR197##  CH.sub.3 CH.sub.2  CN CH CN              551 &#34; &#34; CH.sub.2  NO.sub.2 &#34; &#34;                           552 &#34; &#34; CH.sub.2 COOC.sub.2 H.sub.5 &#34; &#34; 553 &#34; &#34;  ##STR198##  &#34; &#34; 554 &#34; &#34;  ##STR199##  &#34; &#34; 555 &#34; &#34;  ##STR200##  &#34; &#34; 556 &#34; &#34;  ##STR201##  &#34; &#34; 557 &#34; C.sub.2  H.sub.5 H &#34; &#34;                                               558 &#34; &#34; CH.sub.3 &#34; &#34;  559 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              560 &#34; C.sub.3 H.sub.7  (i) H &#34; &#34;                                                         561 &#34; &#34; CH.sub.3 &#34; &#34; 562  ##STR202##  C.sub.3 H.sub.7 (i) C.sub.2  H.sub.5 CH CN                        563 &#34;  ##STR203##  H &#34; &#34; 564 &#34; &#34; CH.sub.3 &#34; &#34;  565 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              566 &#34; CH.sub.2 CHCH.sub.2   H &#34; &#34;                                                         567 &#34; &#34; CH.sub.3 &#34; &#34;  568 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;            569 &#34;  ##STR204##  H &#34; &#34; 570 &#34; &#34; CH.sub.3 &#34; &#34;  571 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              572 &#34; CHO H &#34; &#34;  573 &#34; &#34; CH.sub.3 &#34; &#34; 574  ##STR205##  CHO C.sub.2  H.sub.5 CH CN        575 &#34; COCH.sub.3 H &#34; &#34;  576 &#34; &#34; CH.sub.3 &#34; &#34;  577 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              578 &#34; SO.sub.2 CH.sub.3 H &#34; &#34;  579 &#34; &#34; CH.sub.3 &#34; &#34;  580 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              581 &#34; COOC.sub. 2  H.sub.5 H &#34; &#34; 582 &#34; &#34; CH.sub.3 &#34; &#34;  583 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              584 &#34; OC.sub.2 H.sub.5 H &#34; &#34;  585 &#34; &#34; CH.sub.3 &#34; &#34;  586 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              587 &#34; CH.sub.2 CCH H &#34; &#34;  588 &#34; &#34; CH.sub.3 &#34; &#34;  589 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;            590  ##STR206##  H CH.sub.3 CH CN 591 &#34; CH.sub.3 &#34; &#34; &#34; 592  ##STR207##  H &#34; &#34; &#34; 593 &#34; CH.sub.3 &#34; &#34; &#34; 594  ##STR208##  H &#34; &#34; &#34; 595 &#34; CH.sub.3 &#34; &#34; &#34; 596  ##STR209##  H &#34; &#34; &#34; 597 &#34; CH.sub.3 &#34; &#34; &#34; 598  ##STR210##  H &#34; &#34; &#34; 599 &#34; CH.sub.3 &#34; &#34; &#34; 600  ##STR211##  H &#34; &#34; &#34; 601 &#34; CH.sub.3 &#34; &#34; &#34; 602  ##STR212##  H CH.sub.3 CH CN 603 &#34; CH.sub.3 &#34; &#34; &#34; 604  ##STR213##  H &#34; &#34; &#34; 605 &#34; CH.sub.3 &#34; &#34; &#34; 606  ##STR214##  H &#34; &#34; &#34; 607 &#34; CH.sub.3 &#34; &#34; &#34; 608  ##STR215##  H &#34; &#34; &#34; 609 &#34; CH.sub.3 &#34; &#34; &#34; 610  ##STR216##  H &#34; &#34; &#34; 611 &#34; CH.sub.3 &#34; &#34; &#34; 612  ##STR217##  H &#34; &#34; &#34; 613 &#34; CH.sub.3 &#34; &#34; &#34; 614  ##STR218##  H CH.sub.3 CH CN 615 &#34; CH.sub.3 &#34; &#34; &#34; 616  ##STR219##  H &#34; &#34; &#34; 617 &#34; CH.sub.3 &#34; &#34; &#34; 618  ##STR220##  H &#34; &#34; &#34; 619 &#34; CH.sub.3 &#34; &#34; &#34; 620  ##STR221##  H &#34; &#34; &#34; 621 &#34; CH.sub.3 &#34; &#34; &#34; 622  ##STR222##  H &#34; &#34; &#34; 623 &#34; CH.sub.3 &#34; &#34; &#34; 624  ##STR223##  H CH.sub.3 CH CN 625 &#34; CH.sub.3 &#34; &#34; &#34; 626  ##STR224##  H &#34; &#34; &#34; 627 &#34; CH.sub.3 &#34; &#34; &#34; 628  ##STR225##  H &#34; &#34; &#34; 629 &#34; CH.sub.3 &#34; &#34; &#34; 630  ##STR226##  H &#34; &#34; &#34; 631 &#34; CH.sub.3 &#34; &#34; &#34; 632  ##STR227##  H &#34; &#34; &#34; 633 &#34; CH.sub.3 &#34; &#34; &#34; 634  ##STR228##  H &#34; &#34; &#34; 635  ##STR229##  CH.sub.3 CH.sub.3 CH CN 636  ##STR230##  H &#34; &#34; &#34; 637 &#34; CH.sub.3 &#34; &#34; &#34; 638  ##STR231##  H &#34; &#34; &#34; 639 &#34; CH.sub.3 &#34; &#34; &#34; 640  ##STR232##  H &#34; &#34; &#34; 641 &#34; CH.sub.3 &#34; &#34; &#34; 642  ##STR233##  H &#34; &#34; &#34; 643 &#34; CH.sub.3 &#34; &#34; &#34; 644  ##STR234##  H CH.sub.3 CH CN 645 &#34; CH.sub.3 &#34; &#34; &#34; 646  ##STR235##  H &#34; &#34; &#34; 647 &#34; CH.sub.3 &#34; &#34; &#34; 648  ##STR236##  H &#34; &#34; &#34; 649 &#34; CH.sub.3 &#34; &#34; &#34;  650 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              651 &#34; C.sub.2 H.sub.5 CH.sub.3 &#34; &#34; 652  ##STR237##  H CH.sub.3 CH CN 653 &#34; CH.sub.3 &#34; &#34; &#34; 654  ##STR238##  H &#34; &#34; &#34; 655 &#34; CH.sub.3 &#34; &#34; &#34; 656  ##STR239##  H &#34; &#34; &#34; 657 &#34; CH.sub.3 &#34; &#34; &#34; 658  ##STR240##  H &#34; &#34; &#34; 659 &#34; CH.sub.3 &#34; &#34; &#34; 660  ##STR241##  H &#34; &#34; &#34; 661 &#34; CH.sub.3 &#34; &#34; &#34; 662  ##STR242##  H &#34; &#34; &#34; 663 &#34; CH.sub.3 &#34; &#34; &#34; 664  ##STR243##  H H CH CN 665 &#34; &#34; CH.sub.3 &#34; &#34;  666 &#34; &#34; CH.sub.2  Cl &#34; &#34;                                                  667 &#34; &#34; C.sub.2 H.sub.5 &#34; &#34;  668 &#34; &#34; C.sub.3 H.sub.7  (i) &#34; &#34;                                          669 &#34; &#34; C.sub.4 H.sub.9  (t) &#34; &#34;                                                           670 &#34; CH.sub.3 H &#34; &#34;  671 &#34; &#34; CH.sub.3 &#34; &#34;  672 &#34; &#34; CH.sub.2  Cl &#34; &#34;                                                  673 &#34; &#34; C.sub.2 H.sub.5 &#34; &#34; 674 &#34; &#34;  ##STR244##  &#34; &#34; 675  ##STR245##  CH.sub.3 C.sub.3 H.sub.7  (i) CH CN                     676 &#34; &#34; C.sub.4 H.sub.9  (t) &#34; &#34;                  677 &#34; C.sub.2  H.sub.5 H &#34; &#34;                     678 &#34; &#34; CH.sub.3 &#34; &#34;  679 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;            680 &#34;  ##STR246##  H &#34; &#34; 681 &#34; &#34; CH.sub.3 &#34; &#34;  682 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              683 &#34; COCH.sub. 3 H &#34; &#34;  684 &#34; &#34; CH.sub.3 &#34; &#34;  685 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              686 &#34; SO.sub.2 CH.sub.3 H &#34; &#34; 687  ##STR247##  SO.sub.2  CH.sub.3 CH.sub.3 CH CN    688 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34; *1 .sup.1 HNMR(CDCl.sub.3) δ; ppm 3.32 (s, 3H), 4.63 (s, 2H), 7.37 (d, 1H), 7.62 (dd, 1H), 8.37 (d, 1H) 
    
     Further, the following compound is described in U.S. Pat. No. 4,918,088, which has insecticidal activities. ##STR248## The compound however shows no insecticidal activity against lepidopterous insects and green rice leafhopper which are more serious pests on crops, though it shows some activity against cotton aphid. 
     The purpose of this invention is to provide agricultural chemicals which can be advantageously synthesized industrially, have certain effects and may be applied safely. 
     The compound of this invention has high insecticidal activity against both lepidopterous and hemipterous insects. 
     SUMMARY OF THE INVENTION 
     The present invention relates to a compound having the formula ##STR249## wherein R 1  represents an optionally substituted 5-6 membered aromatic hetero ring containing nitrogen atom, except a non-substituted 2-pyridyl; 
     X represents an optionally substituted C 1-3  alkylene or alkylidene; 
     R 2  represents a hydrogen, a carbamoyl, a mono or di C 1-5  alkyl carbamoyl, a thiocarbamoyl, a mono or di C 1  alkylthiocarbamoyl, a sulfamoyl, a mono or di C 1  alkylsulfamoyl, an optionally substituted C 1-5  alkyl, an optionally substituted C 2-5  alkenyl, an optionally substituted C 2-5  alkynyl, an optionally substituted C 3-8  cycloalkyl, an optionally substituted C 3-8  cycloalkenyl, an optionally substituted aryl or --Y--R 5  ; 
     Y represents O, S(O) n , CO, CS or CO 2  ; 
     n represents 0,1 or 2; 
     R 5  represents a hydrogen, an optionally substituted C 1-5  alkyl, an optionally substituted C 2-5  alkenyl, an optionally substituted C 2-5  alkynyl, an optionally substituted C 3-8  cycloalkyl, an optionally substituted C 3-8  cycloalkenyl or an optionally substituted aryl; 
     R 3  represents a hydrogen, an optionally substituted C 1-5  alkyl, an optionally substituted C 2-5  alkenyl, an optionally substituted C 2-5  alkynyl, an optionally substituted C 3-8  cycloalkyl or an optionally substituted C 3-8  cycloalkenyl; 
     R 4  represents a cyano or a nitro; and Z represents CH or N; or its salt. 
     DESCRIPTION OF THE PREFERRED EMBODIMENTS 
     The compounds of this invention can be prepared in accordance with the following reaction schemes: 
     (1) Preparation Method 1: ##STR250## where r 1  and r 2  represent a C 1-5  alkyl; and R 1 , R 2 , R 3 , R 4  and X are as defined above. 
     The reaction is carried out in an inactive organic solvent, preferably in an aromatic hydrocarbon solvent such as xylene, toluene or benzene, in the presence of acidic catalyst such as p-toluenesulfonic acid, if necessary, under reflux. 
     (2) Preparation method 2: ##STR251## where r 3  represents a C 1-5  alkyl: and R 1 , R 2 , R 3  and X are as defined above. This reaction is carried out in an inactive organic solvent, preferably in an alcohol such as methanol, ethanol, between room temperature and the boiling point of the used solvent. 
     (3) Preparation Method 3: ##STR252## where Hal represents a halogen; and R 1 , R 2 , R 3  and X are as defined above. 
     This reaction is carried out in an inactive organic solvent, preferably DMF, THF, benzene acetonitrile, acetone, methylethylketone, in the presence of acid accepter such as potassium carbonate, NaH, triethylamine, between room temparature and the boiling point of the used solvent. 
     (4) Preparation Method 4: ##STR253## where R 1 , R 2 , R 3 , X and Hal are as defined above. This reaction is carried out in the same manner as that of Preparation Method 3. 
     (5) Preparation Method 5: ##STR254## where R 1 , R 2 , R 3  and X are as defined above. This reaction is carried out in an inactive organic solvent, preferably acetonitrile, carbon tetrachloride, dichloroethane, in the presence of nitration reagent such as nitronium tetrafluoroborate, between -20° C. and the boiling point of the used solvent. 
     After the reaction is completed, an usual after-treatment gives the intended compound. The structure of the compounds of this invention was determined by such means as IR, NMR, MASS, etc. When R 2  is hydrogen in a compound of this invention, tautomers represented by ##STR255## can exist. 
     The syn--aniti isomers, when Z represents N, and the cis-trans isomers, when Z represents CH, as represented by, ##STR256## can also exist. 
     The ratio varies depending on e.g. conditions of instrumental analysis. 
    
    
     EXAMPLES 
     The following examples illustrate the present invention. 
     Example 1 
     2-(2-chloro-5-pyridylmethylamino)-1-nitro-1-butene: ##STR257## In 50 ml of toluene, 4.2 g of 2-chloro-5-pyridylmethylamine, 3.5 g of 1-nitro-2-butanone and 0.1 g of p-toluene sulfonic acid were mixed and the mixture was refluxed for 2 hours. The solvent was then distilled off and the residue was purified by column chromatography on silica gel to afford 4.1 g of compound No. 368. m.p. 95°-98° C. 
     Example 2 
     2-(2-chloro-5-pyridylmethylamino)-1-cyano-1-propene: ##STR258## 1.4 g of 2-chloro-5-pyridylmethylamine and 0.8 g of 1-cyano-2-propanone were mixed and the mixture was stirred at room temperature over night. The solvent was then distilled off and the residue was purified by column chromatography on silica gel to afford 1.7 g of compound No. 528. m.p. 95°-98° C. 
     EXAMPLE 3 
     N-cyano-N&#39;-(2-chloro-5-pyridylmethyl)-N&#39;-methylacetamidine: ##STR259## In 20 ml of ethanol, 1.6 g of N-methyl-2-cloro-5-pyridylmethylamine and 1.2 g of ethyl-N-cyanoacetamidine were mixed and the mixture was stirred at room temperature over night. The solvent was then distilled off and the residue was purified by column chromatography on silica gel to afford 1.8 g of compound No. 22. m.p. 101°-103° C. 
     EXAMPLE 4 
     N-cyano-N&#39;-(2-chloro-5-pyridylmethyl)-N&#39;-ethylacetamidine: ##STR260## 0.7 g of sodium hydride (purity 60%) was added to the solution of 3.0 g of N-cyano-N&#39;-(2-chloro-5-pyridylmethyl)acetamidine in 20 ml of N.N-dimthylformamide at ice bath temperature. After stirring it at the same temperature for 1 hour, 2.7 g of ethyl iodide was added to the mixture, followed by stirring for 5 hours at room temperature. The reaction mixture was then poured into ice-water, extracted with ethyl acetate, dried over anhydrous magnesium sulfate and concentrated under reduced pressre. The residue obtained was purified by column chromatography on silica gel to afford 1.6 g of compound No. 51. m.p. 100°-101° C. 
     EXAMPLE 5 
     N-cyano-N-(2-chloro-5-pyridylmethyl)-N&#39;-methylacetamidine: ##STR261## 0.6 g of sodium hydride (purity 60%) was added to the solution of 1.3 g of N-cyano-N&#39;-methylacetamidine in 20 ml of N,N-dimethylformamide at ice bath temperature. After stirring it at the same temperature for 1 hour, 2.2 g of 2-chloro-5-pyridylmethylchlride was added to the mixture, followed by stirring for 5 hours at room temperature. The reaction mixture was then poured into ice-water, extrated with ethyl acetate, dried over anhydrous magnesium sulfate and concentrated under reduced pressre. The residue obtained was purified by column chromatography on silica gel to afford 1.5 g of compound No. 22 m.p. 101-°103° C. 
     Reference Example 
     N-(2-chloro-5-pyridylmethyl)-N-methylacetamidine hydrochloride: ##STR262## To 40 ml of ethanol was added 5.1 g of N-(2-chloro-5-pyridylmethyl)-N-Methylamine and then 4 g of ethyl acetimidate hydrochloride at 0° C. After stirring for an hour, the reaction mixture was allowed to warm to room temperature and stirred over night. The solvent was then distilled off. The obtained white residue was washed with diethyl ether to afford 7.3 g of the title compound m.p. 192-°197° C. 
     Example 6 
     N-(2-chloro-5-pyridylmethyl)-N-methyl-N&#39;-nitroacetamidine: ##STR263## To a suspension of 1 g of N-(2-chloro-5-pyridylmethyl)-N-methylamidine hydrochloride in 10 ml of dry acetonitrile was added dropwise 0.7 g of DBU under nitrogen at room temperature. After stirring for 30 minutes, the solution was added dropwise to a suspension of 0.6 g of nitronium tetrafluoroborate in 5 ml of dry acetonitrile under nitrogen on cooling with ice-water and let stir for 4 hours. After which time, the mixture was poured into ice-water, then extracted several time with chloroform. The combined chloroform layer was dried over magnesium sulfate, filtered and distilled off. The crude oil was purified by column chromatgraphy on silica gel to afford 0,3 g of compound No. 236. 
     
         N.sub.D.sup.25 1.5808 
    
     Typical examples of this invention including those described above are listed in Table 1. 
     
         TABLE 1  - Structure Formula  ##STR264##                                                                     C ompound No. R.sub.1 X R.sub.2 R.sub.3 Z R.sub.4 Physical Properties [ ] m.p. °C.  1 ##STR265##  H H N CN [123-126]  2 &#34; &#34; CH.sub.3 &#34; &#34; [141-143]   3 &#34; &#34; CH.sub.2  Cl &#34; &#34; [124-126]                                          4 &#34; &#34; CH.sub.2  F &#34; &#34; [151-152]                                                   5 &#34; &#34; CF.sub.3 &#34; &#34; [112-114]   6 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34; [120-122]                                      7 &#34; &#34; C.sub.3 H.sub.7  (n) &#34; &#34; [100-101]  8 &#34; &#34; ##STR266##  &#34; &#34; [193.5-195]              9 &#34; &#34; C.sub.4 H.sub.9  (t) &#34; &#34;                            10 &#34; &#34; CH.sub.2 OCH.sub.3 &#34; &#34; [128-128.5]   11 &#34; &#34; CH.sub.2  SCH.sub.3 &#34; &#34; [116-118]  12 ##STR267##  &#34; CH.sub.2 COOC.sub.2 H.sub.5 N CN n.sub.D  .sup.25.5 1.5608                                        13 &#34; &#34; CH.sub.2 CH.sub.2 COOC.sub.2  H.sub.5 &#34; &#34;                                                     14 &#34; &#34; CH.sub.2  NHCH.sub.3 &#34; &#34;                                                    15 &#34; &#34; CH.sub.2  N(CH.sub.3).sub.2 &#34; &#34;                                           16 &#34; &#34; CH.sub.2 CH.sub.2 CH.sub.2  Cl &#34; &#34; [114-115]  17 &#34; &#34; ##STR268##  &#34; &#34; [190-191]  18 &#34; &#34; CH.sub.2  CN &#34; &#34; [106-108]                                          19 &#34; &#34; CH.sub.2 CH.sub.2  CN &#34; &#34;  20 &#34; &#34; ##STR269##  &#34; &#34; [187-189]  21 &#34; CH.sub.3 H &#34; &#34; n.sub.D  .sup.25 1.5918                                22 &#34; &#34; CH.sub.3 &#34; &#34; [101-103]  23 &#34; &#34; &#34; &#34; &#34; [161-162]  HCl salt   24 &#34; &#34; CH.sub.2 Cl &#34; &#34; n.sub.D  .sup.26.5 1.5921                          25 &#34; &#34; CH.sub.2 F &#34; &#34; [79-80]  26 &#34; &#34; CF.sub.3 &#34; &#34; *1  27 ##STR270##  CH.sub.3 C.sub.2 H.sub.5 N CN n.sub.D  .sup.27 1.5742                                   28 &#34; &#34; C.sub.3 H.sub.7 (n) &#34; &#34; [97-100]  29 &#34; &#34; ##STR271##  &#34; &#34; n.sub.D  .sup.24.5 1.5829         30 &#34; &#34; C.sub.4 H.sub.9  (t) &#34; &#34;                                31 &#34; &#34; CH.sub.2 OCH.sub.3 &#34; &#34; n.sub.D  .sup.24 1.5803                                                     32 &#34; &#34; CH.sub.2 SCH.sub.3 &#34; &#34; n.sub.D  .sup.24.5 1.6070                          33 &#34; &#34; CH.sub.2 COOC.sub.2 H.sub.5 &#34; &#34; n.sub.D  .sup.25.5 1.5604                                       34 &#34; &#34; CH.sub.2 CH.sub.2 COOC.sub.2 H.sub.5 &#34; &#34; n.sub.D  .sup.24.5 1.5605                   35 &#34; &#34; CH.sub.2 NHCH.sub.3 &#34; &#34; n.sub.D  .sup.25 1.5861                                                     36 &#34; &#34; CH.sub.2 N(CH.sub.3).sub.2 &#34; &#34; n.sub.D  .sup.25 1.5577                    37 &#34; &#34; CH.sub.2 CH.sub.2 Cl &#34; &#34;    38 &#34; &#34; CH.sub.2 CH.sub.2 CH.sub.2 Cl &#34; &#34; n.sub.D .sup.25.5 1.5830  39 &#34; &#34; ##STR272##  &#34; &#34;  40 &#34; &#34; ##STR273##  &#34; &#34;  41 &#34; &#34; ##STR274##  &#34; &#34; n.sub.D  .sup.25.5 1.6040  42 ##STR275##  CH.sub.3 CHCH.sub.2   N CN                 43 &#34; &#34; CH.sub.2 CN &#34; &#34; n.sub.D .sup.25 1.5913    44 &#34; &#34; CH.sub.2 CH.sub.2  CN &#34; &#34; [112-114]  45 &#34; &#34; ##STR276##  &#34; &#34;  46 &#34; &#34; ##STR277##  &#34; &#34; [224-226]  47 &#34; CHF.sub.2 H &#34; &#34;   48 &#34; &#34; CH.sub.3 &#34; &#34; n.sub.D  .sup.24.5 1.5423                             49 &#34; &#34; C.sub.2 H.sub.5 &#34; &#34;   50 &#34; C.sub.2  H.sub.5 H &#34; &#34; [101-103]                                     51 &#34; &#34; CH.sub.3 &#34; &#34; [100-101]   52 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                               53 &#34; C.sub.3 H.sub.7  (i) H &#34; &#34; [205-207]                                                54 &#34; &#34; CH.sub.3 &#34; &#34;   55 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;  56 &#34; ##STR278##  H &#34; &#34;  57 ##STR279##  ##STR280##  CH.sub.3 N CN n.sub.D  .sup.25 1.5825                   58 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                          59 &#34; CH.sub.2 OCH.sub.3 H &#34; &#34;   60 &#34; &#34; CH.sub.3 &#34; &#34; n.sub.D  .sup.25.5 1.5711                        61 &#34; CH.sub.2 SCH.sub.3 H &#34; &#34;62 &#34; &#34; CH.sub.3 &#34; &#34; n.sub.D  .sup.25 1.5828                             63 &#34; CH.sub.2 COOC.sub.2 H.sub.5 H &#34; &#34;   64 &#34; &#34; CH.sub.3 &#34; &#34; n.sub.D  .sup.25 1.5475  65 &#34; ##STR281##  H &#34; &#34;  66 &#34; &#34; CH.sub.3 &#34; &#34; n.sub.D  .sup.25.5 1.5928  67 &#34; ##STR282##  H &#34; &#34;  68 &#34; &#34; CH.sub.3 &#34; &#34; n.sub.D  .sup.25.5 1.6155  69 &#34; ##STR283##  H &#34; &#34;  70 &#34; &#34; CH.sub.3 &#34; &#34; n.sub.D  .sup.24.5 1.6093  71 &#34; ##STR284##  H &#34; &#34;  72 ##STR285##  ##STR286##  CH.sub.3 N CN [112-114]  73 &#34; CH.sub.2 CHCH.sub.2  H &#34; &#34; n.sub.D  .sup.25 1.5841                    74 &#34; &#34; CH.sub.3 &#34; &#34; n.sub.D .sup.25 1.5809   75 &#34; CH.sub.2  CCH H &#34; &#34;                                                  76 &#34; &#34; CH.sub.3 &#34; &#34; n.sub.D  .sup.25.5 1.5730                                      77 &#34; CH.sub.2 CN H &#34; &#34;  78 &#34; &#34; CH.sub.3 &#34; &#34; [127-128]  79 &#34; ##STR287##  H &#34; &#34;  80 &#34; &#34; CH.sub.3 &#34; &#34; [124-127]  81 &#34; ##STR288##  H &#34; &#34;  82 &#34; &#34; CH.sub.3 &#34; &#34; n.sub.D  .sup.24.5 1.6045  83 &#34; ##STR289##  H &#34; &#34;  84 &#34; &#34; CH.sub.3 &#34; &#34; n.sub.D  .sup.25.5 1.6092  85 &#34; ##STR290##  H &#34; &#34;  86 ##STR291##  ##STR292##  CH.sub.3 N CN n.sub.D  .sup.25.5 1.5910  87 &#34; ##STR293##  H &#34; &#34;  88 &#34; &#34; CH.sub.3 &#34; &#34; n.sub.D  .sup.25.5 1.6162  89 &#34; ##STR294##  H &#34; &#34;  90 &#34; &#34; CH.sub.3 &#34; &#34; [115-117]  91 &#34; OCH.sub.3 H &#34; &#34;  92 &#34; &#34; CH.sub.3 &#34; &#34; [110-112]  93 &#34; CHO H &#34; &#34;  94 &#34; &#34; CH.sub.3 &#34; &#34;   95 &#34; COCH.sub.3 H &#34; &#34; n.sub.D  .sup.25.5 1.5475                           96 &#34; &#34; CH.sub.3 &#34; &#34; [84-86]    97 &#34; SO.sub.2  CH.sub.3 H &#34; &#34; [160-163]                                  98 &#34; &#34; CH.sub.3 &#34; &#34;  99 &#34; ##STR295##  H &#34; &#34; 100 &#34; &#34; CH.sub.3 &#34; &#34; [112-114] 101  ##STR296##  COOC.sub.2  H.sub.5 H N CN       102 &#34; &#34; CH.sub.3 &#34; &#34; n.sub.D  .sup.25 1.5540                    103 &#34; CONH.sub.2 H &#34; &#34;  104 &#34; &#34; CH.sub.3 &#34; &#34; 105 &#34;  ##STR297##  H &#34; &#34; 106 &#34; &#34; CH.sub.3 &#34; &#34; [89-91]  107 &#34; CONHCH.sub.3 H &#34; &#34;  108 &#34; &#34; CH.sub.3 &#34; &#34;  109 &#34; CSNHCH.sub.3 H &#34; &#34;  110 &#34; &#34; CH.sub.3 &#34; &#34; 111  ##STR298##  H CH.sub.3 &#34; &#34; 112 &#34; CH.sub.3 &#34; &#34; &#34; 113  ##STR299##  H &#34; &#34; &#34; 114 &#34; CH.sub.3 &#34; &#34; &#34; 115  ##STR300##  H &#34; &#34; &#34; [83-85] 116  ##STR301##  CH.sub.3 CH.sub.3 N CN [76-78] 117  ##STR302##  H &#34; &#34; &#34; 118 &#34; CH.sub.3 &#34; &#34; &#34; [145-147] 119  ##STR303##  H &#34; &#34; &#34; 120 &#34; CH.sub.3 &#34; &#34; &#34; n.sub.D  .sup.25 1.5202                        121  ##STR304##  H &#34; &#34; &#34; 122 &#34; CH.sub.3 &#34; &#34; &#34; 123  ##STR305##  H &#34; &#34; &#34; 124 &#34; CH.sub.3 &#34; &#34; &#34; n.sub.D  .sup.25.5 1.5580                        125  ##STR306##  H &#34; &#34; &#34; 126 &#34; CH.sub.3 &#34; &#34; &#34; 127  ##STR307##  H &#34; &#34; &#34; 128 &#34; CH.sub.3 &#34; &#34; &#34; 129  ##STR308##  H &#34; &#34; &#34; [162-163] 130 &#34; CH.sub.3 &#34; &#34; &#34; [105-107] 131  ##STR309##  H CH.sub.3 N CN 132 &#34; CH.sub.3 &#34; &#34; &#34; [138-139] 133  ##STR310##  H &#34; &#34; &#34; 134 &#34; CH.sub.3 &#34; &#34; &#34; n.sub.D  .sup.25 1.5841                        135  ##STR311##  H &#34; &#34; &#34; 136 &#34; CH.sub.3 &#34; &#34; &#34; [107-109] 137  ##STR312##  H &#34; &#34; &#34; 138 &#34; CH.sub.3 &#34; &#34; &#34; 139  ##STR313##  H &#34; &#34; &#34; 140 &#34; CH.sub.3 &#34; &#34; &#34; 141  ##STR314##  H &#34; &#34; &#34; 142 &#34; CH.sub.3 &#34; &#34; &#34; 143  ##STR315##  H &#34; &#34; &#34; [122-124] 144 &#34; CH.sub.3 &#34; &#34; &#34; [110-113] 145  ##STR316##  H CH.sub.3 N CN [66-68] 146 &#34; CH.sub.3 &#34; &#34; &#34; n.sub.D  .sup.24.5 1.5790                        147  ##STR317##  H &#34; &#34; &#34; 148 &#34; CH.sub.3 &#34; &#34; &#34; [94-96] 149  ##STR318##  H &#34; &#34; &#34; [130-132] 150 &#34; CH.sub.3 &#34; &#34; &#34; n.sub.D  .sup.25 1.5612                        151  ##STR319##  H &#34; &#34; &#34; [96-99] 152 &#34; CH.sub.3 &#34; &#34; &#34; n.sub.D  .sup.25.5 1.5800                        153  ##STR320##  H &#34; &#34; &#34; 154 &#34; CH.sub.3 &#34; &#34; &#34; 155  ##STR321##  H &#34; &#34; &#34; 156  ##STR322##  CH.sub.3 CH.sub.3 N CN 157  ##STR323##  H &#34; &#34; &#34; 158 &#34; CH.sub.3 &#34; &#34; &#34; 159  ##STR324##  H &#34; &#34; &#34; 160 &#34; CH.sub.3 &#34; &#34; &#34; 161  ##STR325##  H &#34; &#34; &#34; 162 &#34; CH.sub.3 &#34; &#34; &#34; 163  ##STR326##  H &#34; &#34; &#34; [115-117] 164 &#34; CH.sub.3 &#34; &#34; &#34; n.sub.D  .sup.23 1.5717                        165  ##STR327##  H &#34; &#34; &#34; [104-106] 166 &#34; CH.sub.3 &#34; &#34; &#34; 167  ##STR328##  H CH.sub.3 N CN 168 &#34; CH.sub.3 &#34; &#34; &#34; 169  ##STR329##  H &#34; &#34; &#34; [112-114] 170 &#34; CH.sub.3 &#34; &#34; &#34; n.sub.D  .sup.25 1.5413                        171  ##STR330##  H &#34; &#34; &#34; [122-124] 172 &#34; CH.sub.3 &#34; &#34; &#34; [143-144]  173 &#34; &#34; C.sub.2 H.sub.5 &#34; &#34; n.sub.D  .sup.25 1.5575                       174 &#34; C.sub.2 H.sub.5 CH.sub.3 &#34; &#34; [63-70] 175  ##STR331##  H &#34; &#34; &#34; [149-151] 176 &#34; CH.sub.3 &#34; &#34; &#34; 177  ##STR332##  H H &#34; &#34; [179-183] 178 &#34; CH.sub.3 &#34; &#34; &#34; n.sub.D  .sup.25 1.5952                        179  ##STR333##  H CH.sub.3 N CN 180 &#34; CH.sub.3 &#34; &#34; &#34; 181  ##STR334##  H &#34; &#34; &#34; 182 &#34; CH.sub.3 &#34; &#34; &#34; 183  ##STR335##  H &#34; &#34; &#34; 184 &#34; CH.sub.3 &#34; &#34; &#34; 185  ##STR336##  H &#34; &#34; &#34; 186 &#34; CH.sub.3 &#34; &#34; &#34; 187  ##STR337##  H &#34; &#34; &#34; 188 &#34; CH.sub.3 &#34; &#34; &#34; [106-109] 189  ##STR338##  H CH.sub.3 &#34; &#34; [90-92] 190  ##STR339##  CH.sub.3 CH.sub.3 N CN [102-103] 191  ##STR340##  H &#34; &#34; &#34; 192 &#34; CH.sub.3 &#34; &#34; &#34; 193  ##STR341##  H H &#34; &#34; 194 &#34; &#34; CH.sub.3 &#34; &#34; [127-129]  195 &#34; &#34; CH.sub.2  Cl &#34; &#34;                                                  196 &#34; &#34; CH.sub.2  F &#34; &#34;                                                            197 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;    198 &#34; &#34;  ##STR342##  &#34; &#34; 199 &#34; &#34; CH.sub.2  SCH.sub.3 &#34; &#34;                                            200 &#34; &#34; CH.sub.2  OCH.sub.3 &#34; &#34;   201  ##STR343##  H C.sub.3 H.sub.7 (n) N CN n.sub.D  .sup.25.5 1.5528                               202 &#34; CH.sub.3 H &#34; &#34;  203 &#34; &#34; CH.sub.3 &#34; &#34; n.sub.D  .sup.25.5 1.5798                            204 &#34; &#34; CH.sub.2 Cl &#34; &#34; 205 &#34; &#34; CH.sub.2  F &#34; &#34;                                               206 &#34; H C.sub.2 H.sub.5 &#34; &#34; n.sub.D  .sup.25.5 1.5657               207 &#34; &#34;  ##STR344##  &#34; &#34; 208 &#34; &#34; CH.sub.2  SCH.sub.3 &#34; &#34;                                            209 &#34; &#34; CH.sub.2  OCH.sub.3 &#34; &#34;                                                    210 &#34; &#34; C.sub.3 H.sub.7  (i) &#34; &#34;                                                 211 &#34; &#34; C.sub.4 H.sub.9  (t) &#34; &#34;  212  ##STR345##  C.sub.2  H.sub.5 H N CN   213 &#34; &#34; CH.sub.3 &#34; &#34; n.sub.D  .sup.24.5 1.5665                      214 &#34; &#34; CH.sub.2  Cl &#34; &#34;            215 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                            216 &#34; C.sub.3 H.sub.7 (i) H &#34; &#34;   217 &#34; &#34; CH.sub.3 &#34; &#34;  218 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              219 &#34; COCH.sub. 3 H &#34; &#34;  220 &#34; &#34; CH.sub.3 &#34; &#34;  221 &#34; SO.sub.2  CH.sub.3 H &#34; &#34;                                            222 &#34; &#34; CH.sub.3 &#34; &#34; 223  ##STR346##  H H N NO.sub.2 224 &#34; &#34; CH.sub.3 &#34; &#34;  225 &#34; &#34; CH.sub.2  Cl &#34; &#34;                                                  226 &#34; &#34; CH.sub.2  F &#34; &#34;                                                            227 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;    228 &#34; &#34;  ##STR347##  &#34; &#34; 229 &#34; &#34; CH.sub.2  SCH.sub.3 &#34; &#34;                                            230 &#34; &#34; CH.sub.2  OCH.sub.3 &#34; &#34;                                                    231 &#34; &#34; C.sub.3 H.sub.7  (i) &#34; &#34;                                                 232 &#34; &#34; C.sub.4 H.sub.9  (t) &#34; &#34;                                                           233 &#34; &#34; CHCH.sub.2   &#34; &#34;        234 &#34; &#34;  ##STR348##  &#34; &#34; 235  ##STR349##  CH.sub.3 H N NO.sub.2 236 &#34; &#34; CH.sub.3 &#34; &#34; n.sub.D  .sup.25 1.5808                               237 &#34; &#34; CH.sub.2 Cl &#34; &#34;238 &#34; &#34; CH.sub.2  F &#34; &#34;                                                239 &#34; &#34; C.sub.2 H.sub.5 &#34; &#34; 240 &#34; &#34;  ##STR350##  &#34; &#34; 241 &#34; &#34; CH.sub.2  SCH.sub.3 &#34; &#34;                                            242 &#34; &#34; CH.sub.2  OCH.sub.3 &#34; &#34;                                                    243 &#34; &#34; C.sub.3 H.sub.7  (n) &#34; &#34;                                                 244 &#34; &#34; C.sub.4 H.sub.9  (t) &#34; &#34;                                                           245 &#34; &#34; CHCH.sub.2   &#34; &#34;        246 &#34; &#34;  ##STR351##  &#34; &#34; 247  ##STR352##  C.sub.2  H.sub.5 H N NO.sub.2   248 &#34; &#34; CH.sub.3 &#34; &#34;  249 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              250 &#34; C.sub.3 H.sub.7  (i) H &#34; &#34;                                                         251 &#34; &#34; CH.sub.3 &#34; &#34;  252 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;            253 &#34;  ##STR353##  H &#34; &#34; 254 &#34; &#34; CH.sub.3 &#34; &#34;  255 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              256 &#34; COCH.sub. 3 H &#34; &#34;  257 &#34; &#34; CH.sub.3 &#34; &#34;  258 &#34; SO.sub.2  CH.sub.3 H &#34; &#34;                                            259 &#34; &#34; CH.sub.3 &#34; &#34; 260  ##STR354##  H CH.sub.3 N NO.sub.2 261 &#34; CH.sub.3 &#34; &#34; &#34; 262  ##STR355##  H &#34; &#34; &#34; 263 &#34; CH.sub.3 &#34; &#34; &#34; 264  ##STR356##  H &#34; &#34; &#34; 265 &#34; CH.sub.3 &#34; &#34; &#34; 266  ##STR357##  H &#34; &#34; &#34; 267 &#34; CH.sub.3 &#34; &#34; &#34; 268  ##STR358##  H &#34; &#34; &#34; 269 &#34; CH.sub.3 &#34; &#34; &#34; 270  ##STR359##  H &#34; &#34; &#34; 271 &#34; CH.sub.3 &#34; &#34; &#34; 272  ##STR360##  H CH.sub.3 N NO.sub.2 273 &#34; CH.sub.3 &#34; &#34; &#34; 274  ##STR361##  H &#34; &#34; &#34; 275 &#34; CH.sub.3 &#34; &#34; &#34; 276  ##STR362##  H &#34; &#34; &#34; 277 &#34; CH.sub.3 &#34; &#34; &#34; 278  ##STR363##  H &#34; &#34; &#34; 279 &#34; CH.sub.3 &#34; &#34; &#34; 280  ##STR364##  H &#34; &#34; &#34; 281 &#34; CH.sub.3 &#34; &#34; &#34; 282  ##STR365##  H &#34; &#34; &#34; 283 &#34; CH.sub.3 &#34; &#34; &#34; 284  ##STR366##  H CH.sub.3 N NO.sub.2 285 &#34; CH.sub.3 &#34; &#34; &#34; 286  ##STR367##  H &#34; &#34; &#34; 287 &#34; CH.sub.3 &#34; &#34; &#34; 288  ##STR368##  H &#34; &#34; &#34; 289 &#34; CH.sub.3 &#34; &#34; &#34; 290  ##STR369##  H &#34; &#34; &#34; 291 &#34; CH.sub.3 &#34; &#34; &#34; 292  ##STR370##  H &#34; &#34; &#34; 293 &#34; CH.sub.3 &#34; &#34; &#34; 294  ##STR371##  H CH.sub.3 N NO.sub.2 295 &#34; CH.sub.3 &#34; &#34; &#34; 296  ##STR372##  H &#34; &#34; &#34; 297 &#34; CH.sub.3 &#34; &#34; &#34; 298  ##STR373##  H &#34; &#34; &#34; 299 &#34; CH.sub.3 &#34; &#34; &#34; 300  ##STR374##  H &#34; &#34; &#34; 301 &#34; CH.sub.3 &#34; &#34; &#34; 302  ##STR375##  H &#34; &#34; &#34; 303 &#34; CH.sub.3 &#34; &#34; &#34; 304  ##STR376##  H &#34; &#34; &#34; 305  ##STR377##  CH.sub.3 CH.sub.3 N NO.sub.2 306  ##STR378##  H &#34; &#34; &#34; 307 &#34; CH.sub.3 &#34; &#34; &#34; 308  ##STR379##  H &#34; &#34; &#34; 309 &#34; CH.sub.3 &#34; &#34; &#34; 310  ##STR380##  H &#34; &#34; &#34; 311 &#34; CH.sub.3 &#34; &#34; &#34; 312  ##STR381##  H &#34; &#34; &#34; 313 &#34; CH.sub.3 &#34; &#34; &#34; 314  ##STR382##  H CH.sub.3 N NO.sub.2 315 &#34; CH.sub.3 &#34; &#34; &#34; 316  ##STR383##  H &#34; &#34; &#34; 317 &#34; CH.sub.3 &#34; &#34; &#34; 318  ##STR384##  H &#34; &#34; &#34; 319 &#34; CH.sub.3 &#34; &#34; &#34;  320 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              321 &#34; C.sub.2 H.sub.5 CH.sub.3 &#34; &#34; 322  ##STR385##  H &#34; &#34; &#34; 323 &#34; CH.sub.3 &#34; &#34; &#34; 324  ##STR386##  H CH.sub.3 N NO.sub.2 325 &#34; CH.sub.3 &#34; &#34; &#34; 326  ##STR387##  H &#34; &#34; &#34; 327 &#34; CH.sub.3 &#34; &#34; &#34; 328  ##STR388##  H &#34; &#34; &#34; 329 &#34; CH.sub.3 &#34; &#34; &#34; 330  ##STR389##  H &#34; &#34; &#34; 331 &#34; CH.sub.3 &#34; &#34; &#34; 332  ##STR390##  H &#34; &#34; &#34; 333 &#34; CH.sub.3 &#34; &#34; &#34; 334  ##STR391##  H &#34; &#34; &#34; 335 &#34; CH.sub.3 &#34; &#34; &#34; 336  ##STR392##  H H N NO.sub.2 337 &#34; &#34; CH.sub.3 &#34; &#34;  338 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              339 &#34; &#34; CH.sub.2  Cl &#34; &#34;                                                           340 &#34; &#34; CH.sub.2  F &#34; &#34;     341 &#34; &#34;  ##STR393##  &#34; &#34; 342 &#34; &#34; CH.sub.2  SCH.sub.3 &#34; &#34;                                            343 &#34; &#34; CH.sub.2  OCH.sub.3 &#34; &#34;   344  ##STR394##  CH.sub.3 H N NO.sub.2 345 &#34; &#34; CH.sub.3 &#34; &#34;  346 &#34; &#34; CH.sub.2  Cl &#34; &#34;                                                  347 &#34; &#34; CH.sub.2  F &#34; &#34;                                                            348 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;    349 &#34; &#34;  ##STR395##  &#34; &#34; 350 &#34; &#34; CH.sub.2  SCH.sub.3 &#34; &#34;                                            351 &#34; &#34; CH.sub.2  OCH.sub.3 &#34; &#34;                                                    352 &#34; &#34; C.sub.3 H.sub.7  (i) &#34; &#34;                                                 353 &#34; &#34; C.sub.4 H.sub.9  (t) &#34; &#34;  354  ##STR396##  C.sub.2  H.sub.5 H N NO.sub.2   355 &#34; &#34; CH.sub.3 &#34; &#34;  356 &#34; &#34; CH.sub.2  Cl &#34; &#34;                                                  357 &#34; &#34; C.sub.2 H.sub.5 &#34; &#34;  358 &#34; C.sub.3 H.sub.7  (i) H &#34; &#34;                                          359 &#34; &#34; CH.sub.3 &#34; &#34;  360 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              361 &#34; COCH.sub. 3 H &#34; &#34;  362 &#34; &#34; CH.sub.3 &#34; &#34;  363 &#34; SO.sub.2  CH.sub.3 H &#34; &#34;                                            364 &#34; &#34; CH.sub.3 &#34; &#34; 365  ##STR397##  H H CH NO.sub.2 [116-118] 366 &#34; &#34; CH.sub.3 &#34; &#34; [133-135]  367 &#34; &#34; CH.sub.2  Cl &#34; &#34;                                                  368 &#34; &#34; C.sub.2 H.sub.5 &#34; &#34; [95-98]  369 &#34; &#34; C.sub.3 H.sub.7  (i) &#34; &#34; [150-152]                                370 &#34; &#34; C.sub.4 H.sub.7  (t) &#34; &#34;                                                           371 &#34; &#34; CHCH.sub.2   &#34; &#34;                                                         372 &#34; &#34; CHCHCH.sub.3 &#34; &#34;  373 &#34; &#34; CH.sub.2  CN &#34; &#34;                                                  374 &#34; &#34; CH.sub.2  NO.sub.2 &#34; &#34;                                                     375 &#34; &#34; CH.sub.2 COOC.sub.2  H.sub.5 &#34; &#34;                 376  ##STR398##  H  ##STR399##  CH NO.sub.2 377 &#34; &#34;  ##STR400##  &#34; &#34; 378 &#34; &#34;  ##STR401##  &#34; &#34; 379 &#34; &#34;  ##STR402##  &#34; &#34; 380 &#34; CH.sub.3 H &#34; &#34;  381 &#34; &#34; CH.sub.3 &#34; &#34; [79-82]  382 &#34; &#34; CH.sub.2  Cl &#34; &#34;                                                  383 &#34; &#34; C.sub.2 H.sub.5 &#34; &#34; [101-104]  384 &#34; &#34; C.sub.3 H.sub.7  (i) &#34; &#34;                                          385 &#34; &#34; C.sub.4 H.sub.7  (t) &#34; &#34;                                                           386 &#34; &#34; CHCH.sub.2   &#34; &#34;                                                         387 &#34; &#34; CHCHCH.sub.3 &#34; &#34; 388  ##STR403##  CH.sub.3 CH.sub.2  CN CH NO.sub.2              389 &#34; &#34; CH.sub.2  NO.sub.2 &#34; &#34;                           390 &#34; &#34; CH.sub.2 COOC.sub.2 H.sub.5 &#34; &#34; 391 &#34; &#34;  ##STR404##  &#34; &#34; 392 &#34; &#34;  ##STR405##  &#34; &#34; 393 &#34; &#34;  ##STR406##  &#34; &#34; 394 &#34; &#34;  ##STR407##  &#34; &#34; 395 &#34; C.sub.2  H.sub.5 H &#34; &#34;                                               396 &#34; &#34; CH.sub.3 &#34; &#34;  397 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              398 &#34; C.sub.3 H.sub.7  (i) H &#34; &#34;                                                         399 &#34; &#34; CH.sub.3 &#34; &#34; 400  ##STR408##  C.sub.3 H.sub.7 (i) C.sub.2  H.sub.5 CH NO.sub.2                        401 &#34;  ##STR409##  H &#34; &#34; 402 &#34; &#34; CH.sub.3 &#34; &#34;  403 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              404 &#34; CH.sub.2 CHCH.sub.2   H &#34; &#34;                                                         405 &#34; &#34; CH.sub.3 &#34; &#34;  406 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;            407 &#34;  ##STR410##  H &#34; &#34; 408 &#34; &#34; CH.sub.3 &#34; &#34;  409 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              410 &#34; CHO H &#34; &#34;  411 &#34; &#34; CH.sub.3 &#34; &#34; 412  ##STR411##  CHO C.sub.2  H.sub.5 CH NO.sub.2        413 &#34; COCH.sub.3 H &#34; &#34;  414 &#34; &#34; CH.sub.3 &#34; &#34;  415 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              416 &#34; SO.sub.2 CH.sub.3 H &#34; &#34;  417 &#34; &#34; CH.sub.3 &#34; &#34;  418 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              419 &#34; COOC.sub. 2  H.sub.5 H &#34; &#34; 420 &#34; &#34; CH.sub.3 &#34; &#34;  421 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              422 &#34; OC.sub.2 H.sub.5 H &#34; &#34;  423 &#34; &#34; CH.sub.3 &#34; &#34;  424 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              425 &#34; CH.sub.2 CCH H &#34; &#34;  426 &#34; &#34; CH.sub.3 &#34; &#34;  427 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;            428  ##STR412##  H CH.sub.3 CH NO.sub.2 429 &#34; CH.sub.3 &#34; &#34; &#34; 430  ##STR413##  H &#34; &#34; &#34; 431 &#34; CH.sub.3 &#34; &#34; &#34; 432  ##STR414##  H &#34; &#34; &#34; 433 &#34; CH.sub.3 &#34; &#34; &#34; 434  ##STR415##  H &#34; &#34; &#34; 435 &#34; CH.sub.3 &#34; &#34; &#34; 436  ##STR416##  H &#34; &#34; &#34; 437 &#34; CH.sub.3 &#34; &#34; &#34; 438  ##STR417##  H &#34; &#34; &#34; 439 &#34; CH.sub.3 &#34; &#34; &#34; 440  ##STR418##  H CH.sub.3 CH NO.sub.2 441 &#34; CH.sub.3 &#34; &#34; &#34; 442  ##STR419##  H &#34; &#34; &#34; 443 &#34; CH.sub.3 &#34; &#34; &#34; 444  ##STR420##  H &#34; &#34; &#34; 445 &#34; CH.sub.3 &#34; &#34; &#34; 446  ##STR421##  H &#34; &#34; &#34; 447 &#34; CH.sub.3 &#34; &#34; &#34; 448  ##STR422##  H &#34; &#34; &#34; 449 &#34; CH.sub.3 &#34; &#34; &#34; 450  ##STR423##  H &#34; &#34; &#34; 451 &#34; CH.sub.3 &#34; &#34; &#34; 452  ##STR424##  H CH.sub.3 CH NO.sub.2 453 &#34; CH.sub.3 &#34; &#34; &#34; 454  ##STR425##  H &#34; &#34; &#34; 455 &#34; CH.sub.3 &#34; &#34; &#34; 456  ##STR426##  H &#34; &#34; &#34; 457 &#34; CH.sub.3 &#34; &#34; &#34; 458  ##STR427##  H &#34; &#34; &#34; 459 &#34; CH.sub.3 &#34; &#34; &#34; 460  ##STR428##  H &#34; &#34; &#34; 461 &#34; CH.sub.3 &#34; &#34; &#34; 462  ##STR429##  H CH.sub.3 CH NO.sub.2 463 &#34; CH.sub.3 &#34; &#34; &#34; 464  ##STR430##  H &#34; &#34; &#34; 465 &#34; CH.sub.3 &#34; &#34; &#34; 466  ##STR431##  H &#34; &#34; &#34; 467 &#34; CH.sub.3 &#34; &#34; &#34; 468  ##STR432##  H &#34; &#34; &#34; 469 &#34; CH.sub.3 &#34; &#34; &#34; 470  ##STR433##  H &#34; &#34; &#34; 471 &#34; CH.sub.3 &#34; &#34; &#34; 472  ##STR434##  H &#34; &#34; &#34; 473  ##STR435##  CH.sub.3 CH.sub.3 CH NO.sub.2 474  ##STR436##  H &#34; &#34; &#34; 475 &#34; CH.sub.3 &#34; &#34; &#34; 476  ##STR437##  H &#34; &#34; &#34; 477 &#34; CH.sub.3 &#34; &#34; &#34; 478  ##STR438##  H &#34; &#34; &#34; 479 &#34; CH.sub.3 &#34; &#34; &#34; 480  ##STR439##  H &#34; &#34; &#34; 481 &#34; CH.sub.3 &#34; &#34; &#34; 482  ##STR440##  H &#34; &#34; &#34; 483 &#34; CH.sub.3 &#34; &#34; &#34; 484  ##STR441##  H CH.sub.3 CH NO.sub.2 485 &#34; CH.sub.3 &#34; &#34; &#34; 486  ##STR442##  H &#34; &#34; &#34; 487 &#34; CH.sub.3 &#34; &#34; &#34;  488 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              489 &#34; C.sub.2 H.sub.5 CH.sub.3 &#34; &#34; 490  ##STR443##  H &#34; &#34; &#34; 491 &#34; CH.sub.3 &#34; &#34; &#34; 492  ##STR444##  H &#34; &#34; &#34; 493 &#34; CH.sub.3 &#34; &#34; &#34; 494  ##STR445##  H &#34; &#34; &#34; 495 &#34; CH.sub.3 &#34; &#34; &#34; 496  ##STR446##  H CH.sub.3 CH NO.sub.2 497 &#34; CH.sub.3 &#34; &#34; &#34; 498  ##STR447##  H &#34; &#34; &#34; 499 &#34; CH.sub.3 &#34; &#34; &#34; 500  ##STR448##  H &#34; &#34; &#34; 501 &#34; CH.sub.3 &#34; &#34; &#34; 502  ##STR449##  H H CH NO.sub.2 503 &#34; &#34; CH.sub.3 &#34; &#34;  504 &#34; &#34; CH.sub.2  Cl &#34; &#34;                                                  505 &#34; &#34; C.sub.2 H.sub.5 &#34; &#34;  506 &#34; &#34; C.sub.3 H.sub.7  (i) &#34; &#34;                                          507 &#34; &#34; C.sub.4 H.sub.9  (t) &#34; &#34;                                                           508 &#34; CH.sub.3 H &#34; &#34;  509 &#34; &#34; CH.sub.3 &#34; &#34;  510 &#34; &#34; CH.sub.2  Cl &#34; &#34;                                                  511 &#34; &#34; C.sub.2 H.sub.5 &#34; &#34; 512 &#34; &#34;  ##STR450##  &#34; &#34; 513  ##STR451##  CH.sub.3 C.sub.3 H.sub.7  (i) CH NO.sub.2                     514 &#34; &#34; C.sub.4 H.sub.9  (t) &#34; &#34;                  515 &#34; C.sub.2  H.sub.5 H &#34; &#34;                     516 &#34; &#34; CH.sub.3 &#34; &#34;  517 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;            518 &#34;  ##STR452##  H &#34; &#34; 519 &#34; &#34; CH.sub.3 &#34; &#34;  520 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              521 &#34; COCH.sub. 3 H &#34; &#34;  522 &#34; &#34; CH.sub.3 &#34; &#34;  523 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              524 &#34; SO.sub.2 CH.sub.3 H &#34; &#34;  525 &#34; &#34; CH.sub.3 &#34; &#34;  526 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;            527  ##STR453##  H H CH CN 528 &#34; &#34; CH.sub.3 &#34; &#34; [95-98]  529 &#34; &#34; CH.sub.2  Cl &#34; &#34;                                                  530 &#34; &#34; C.sub.2 H.sub.5 &#34; &#34;  531 &#34; &#34; C.sub.3 H.sub.7  (i) &#34; &#34;                                          532 &#34; &#34; C.sub.4 H.sub.9  (t) &#34; &#34;                                                           533 &#34; &#34; CHCH.sub.2   &#34; &#34;                                                         534 &#34; &#34; CHCHCH.sub.3 &#34; &#34;  535 &#34; &#34; CH.sub.2  CN &#34; &#34;                                                  536 &#34; &#34; CH.sub.2  NO.sub.2 &#34; &#34;                                                     537 &#34; &#34; CH.sub.2 COOC.sub.2  H.sub.5 &#34; &#34;                 538  ##STR454##  H  ##STR455##  CH CN 539 &#34; &#34;  ##STR456##  &#34; &#34; 540 &#34; &#34;  ##STR457##  &#34; &#34; 541 &#34; &#34;  ##STR458##  &#34; &#34; 542 &#34; CH.sub.3 H &#34; &#34;  543 &#34; &#34; CH.sub.3 &#34; &#34; n.sub.D  .sup.29 1.5941                              544 &#34; &#34; CH.sub.2 Cl &#34; &#34; 545 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                          546 &#34; &#34; C.sub.3 H.sub.7  (i) &#34; &#34;                                                           547 &#34; &#34; C.sub.4 H.sub.9  (t) &#34; &#34;                                                 548 &#34; &#34; CHCH.sub.2   &#34; &#34;                                                           549 &#34; &#34; CHCHCH.sub.3 &#34; &#34; 550  ##STR459##  CH.sub.3 CH.sub.2  CN CH CN              551 &#34; &#34; CH.sub.2  NO.sub.2 &#34; &#34;                           552 &#34; &#34; CH.sub.2 COOC.sub.2 H.sub.5 &#34; &#34; 553 &#34; &#34;  ##STR460##  &#34; &#34; 554 &#34; &#34;  ##STR461##  &#34; &#34; 555 &#34; &#34;  ##STR462##  &#34; &#34; 556 &#34; &#34;  ##STR463##  &#34; &#34; 557 &#34; C.sub.2  H.sub.5 H &#34; &#34;                                               558 &#34; &#34; CH.sub.3 &#34; &#34;  559 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              560 &#34; C.sub.3 H.sub.7  (i) H &#34; &#34;                                                         561 &#34; &#34; CH.sub.3 &#34; &#34; 562  ##STR464##  C.sub.3 H.sub.7 (i) C.sub.2  H.sub.5 CH CN                        563 &#34;  ##STR465##  H &#34; &#34; 564 &#34; &#34; CH.sub.3 &#34; &#34;  565 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              566 &#34; CH.sub.2 CHCH.sub.2   H &#34; &#34;                                                         567 &#34; &#34; CH.sub.3 &#34; &#34;  568 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;            569 &#34;  ##STR466##  H &#34; &#34; 570 &#34; &#34; CH.sub.3 &#34; &#34;  571 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              572 &#34; CHO H &#34; &#34;  573 &#34; &#34; CH.sub.3 &#34; &#34; 574  ##STR467##  CHO C.sub.2  H.sub.5 CH CN        575 &#34; COCH.sub.3 H &#34; &#34;  576 &#34; &#34; CH.sub.3 &#34; &#34;  577 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              578 &#34; SO.sub.2 CH.sub.3 H &#34; &#34;  579 &#34; &#34; CH.sub.3 &#34; &#34;  580 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              581 &#34; COOC.sub. 2  H.sub.5 H &#34; &#34; 582 &#34; &#34; CH.sub.3 &#34; &#34;  583 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              584 &#34; OC.sub.2 H.sub.5 H &#34; &#34;  585 &#34; &#34; CH.sub.3 &#34; &#34;  586 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              587 &#34; CH.sub.2 CCH H &#34; &#34;  588 &#34; &#34; CH.sub.3 &#34; &#34;  589 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;            590  ##STR468##  H CH.sub.3 CH CN 591 &#34; CH.sub.3 &#34; &#34; &#34; 592  ##STR469##  H &#34; &#34; &#34; 593 &#34; CH.sub.3 &#34; &#34; &#34; 594  ##STR470##  H &#34; &#34; &#34; 595 &#34; CH.sub.3 &#34; &#34; &#34; 596  ##STR471##  H &#34; &#34; &#34; 597 &#34; CH.sub.3 &#34; &#34; &#34; 598  ##STR472##  H &#34; &#34; &#34; 599 &#34; CH.sub.3 &#34; &#34; &#34; 600  ##STR473##  H &#34; &#34; &#34; 601 &#34; CH.sub.3 &#34; &#34; &#34; 602  ##STR474##  H CH.sub.3 CH CN 603 &#34; CH.sub.3 &#34; &#34; &#34; 604  ##STR475##  H &#34; &#34; &#34; 605 &#34; CH.sub.3 &#34; &#34; &#34; 606  ##STR476##  H &#34; &#34; &#34; 607 &#34; CH.sub.3 &#34; &#34; &#34; 608  ##STR477##  H &#34; &#34; &#34; 609 &#34; CH.sub.3 &#34; &#34; &#34; 610  ##STR478##  H &#34; &#34; &#34; 611 &#34; CH.sub.3 &#34; &#34; &#34; 612  ##STR479##  H &#34; &#34; &#34; 613 &#34; CH.sub.3 &#34; &#34; &#34; 614  ##STR480##  H CH.sub.3 CH CN 615 &#34; CH.sub.3 &#34; &#34; &#34; 616  ##STR481##  H &#34; &#34; &#34; 617 &#34; CH.sub.3 &#34; &#34; &#34; 618  ##STR482##  H &#34; &#34; &#34; 619 &#34; CH.sub.3 &#34; &#34; &#34; 620  ##STR483##  H &#34; &#34; &#34; 621 &#34; CH.sub.3 &#34; &#34; &#34; 622  ##STR484##  H &#34; &#34; &#34; 623 &#34; CH.sub.3 &#34; &#34; &#34; 624  ##STR485##  H CH.sub.3 CH CN 625 &#34; CH.sub.3 &#34; &#34; &#34; 626  ##STR486##  H &#34; &#34; &#34; 627 &#34; CH.sub.3 &#34; &#34; &#34; 628  ##STR487##  H &#34; &#34; &#34; 629 &#34; CH.sub.3 &#34; &#34; &#34; 630  ##STR488##  H &#34; &#34; &#34; 631 &#34; CH.sub.3 &#34; &#34; &#34; 632  ##STR489##  H &#34; &#34; &#34; 633 &#34; CH.sub.3 &#34; &#34; &#34; 634  ##STR490##  H &#34; &#34; &#34; 635  ##STR491##  CH.sub.3 CH.sub.3 CH CN 636  ##STR492##  H &#34; &#34; &#34; 637 &#34; CH.sub.3 &#34; &#34; &#34; 638  ##STR493##  H &#34; &#34; &#34; 639 &#34; CH.sub.3 &#34; &#34; &#34; 640  ##STR494##  H &#34; &#34; &#34; 641 &#34; CH.sub.3 &#34; &#34; &#34; 642  ##STR495##  H &#34; &#34; &#34; 643 &#34; CH.sub.3 &#34; &#34; &#34; 644  ##STR496##  H CH.sub.3 CH CN 645 &#34; CH.sub.3 &#34; &#34; &#34; 646  ##STR497##  H &#34; &#34; &#34; 647 &#34; CH.sub.3 &#34; &#34; &#34; 648  ##STR498##  H &#34; &#34; &#34; 649 &#34; CH.sub.3 &#34; &#34; &#34;  650 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              651 &#34; C.sub.2 H.sub.5 CH.sub.3 &#34; &#34; 652  ##STR499##  H CH.sub.3 CH CN 653 &#34; CH.sub.3 &#34; &#34; &#34; 654  ##STR500##  H &#34; &#34; &#34; 655 &#34; CH.sub.3 &#34; &#34; &#34; 656  ##STR501##  H &#34; &#34; &#34; 657 &#34; CH.sub.3 &#34; &#34; &#34; 658  ##STR502##  H &#34; &#34; &#34; 659 &#34; CH.sub.3 &#34; &#34; &#34; 660  ##STR503##  H &#34; &#34; &#34; 661 &#34; CH.sub.3 &#34; &#34; &#34; 662  ##STR504##  H &#34; &#34; &#34; 663 &#34; CH.sub.3 &#34; &#34; &#34; 664  ##STR505##  H H CH CN 665 &#34; &#34; CH.sub.3 &#34; &#34;  666 &#34; &#34; CH.sub.2  Cl &#34; &#34;                                                  667 &#34; &#34; C.sub.2 H.sub.5 &#34; &#34;  668 &#34; &#34; C.sub.3 H.sub.7  (i) &#34; &#34;                                          669 &#34; &#34; C.sub.4 H.sub.9  (t) &#34; &#34;                                                           670 &#34; CH.sub.3 H &#34; &#34;  671 &#34; &#34; CH.sub.3 &#34; &#34;  672 &#34; &#34; CH.sub.2  Cl &#34; &#34;                                                  673 &#34; &#34; C.sub.2 H.sub.5 &#34; &#34; 674 &#34; &#34;  ##STR506##  &#34; &#34; 675  ##STR507##  CH.sub.3 C.sub.3 H.sub.7  (i) CH CN                     676 &#34; &#34; C.sub.4 H.sub.9  (t) &#34; &#34;                  677 &#34; C.sub.2  H.sub.5 H &#34; &#34;                     678 &#34; &#34; CH.sub.3 &#34; &#34;  679 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;            680 &#34;  ##STR508##  H &#34; &#34; 681 &#34; &#34; CH.sub.3 &#34; &#34;  682 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              683 &#34; COCH.sub. 3 H &#34; &#34;  684 &#34; &#34; CH.sub.3 &#34; &#34;  685 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34;                                              686 &#34; SO.sub.2 CH.sub.3 H &#34; &#34; 687  ##STR509##  SO.sub.2  CH.sub.3 CH.sub.3 CH CN    688 &#34; &#34; C.sub.2  H.sub.5 &#34; &#34; *1 .sup.1 HNMR(CDCl.sub.3) δ; ppm 3.32 (s, 3H), 4.63 (s, 2H), 7.37 (d, 1H), 7.62 (dd, 1H), 8.37 (d, 1H) 
    
     The compounds of this invention exhibit high insecticidal activities against various species of insect pests such as cutworms, diamondback moth, aphids, leafhoppers and planthoppers. In recent years the decrease of the control effects of organophosphorus and carbamate insecticides, which is caused by the development of resistance to these insecticides, has become serious problem. In such situations, the development of new insecticides which is effective on the resistant pests has been desired. The compounds of this invention possess superior insecticidal activities against not only susceptible strains but also resistant ones. 
     The insecticides covered by this invention contain as active ingredients one or more types of the compounds as expressed by the general formula (1). These active ingredients, may be used as-produced but normally they are used in any of the forms which ordinary agricultural chemicals can take, namely wettable powder, dust, emulsifiable concentrate, suspension concentrates, smoking chemicals, fumigant, granule, or other formulations. For additives and carriers are used soybean flour, wheat flour or other vegetable flours, diatomaceous earth, apatite, gypsum, talc, pyrophyllite, clay or other fine mineral powders, when solid formulations are intended. 
     When liquid formulations are intended, then for solvents are used kerosene, mineral oil, petroleum, solvent naphtha, xylene, cyclohexane, cyclohexanone, dimethylformamide, dimethylsulfoxide, alcohol, acetone, water, etc. A surface active agent may, if necessary, be added in order to give a homogeneous and suitable formulation. The wettable powders, emulsifiable concentrates, suspension thus obtained are diluted with water concentrates, etc. into suspensions or emulsions of a prescribed concentration, before they are actually sprayed on plants in the field. In the case of dusts or granules, they are directly applied without further processing. 
     It goes without saying that the compound(s) of this invention is effective even alone, but it can be used by mixing with various types of insecticides, acaricides and fungicides. 
     Typical examples of acaricides and insecticides which can be used by mixing with the compounds of this invention are described below: 
     Acaricides (fungicides): 
     chlorobenzilate, chloropropylate, proclonol, bromopropylate, dicofol, dinobuton, binapacryl, chlordimeform, amitraz, propargite, PPPS, benzoximate, hexythiazox, fenbutatin oxide, polynactine, chinomethionat, thioquinox, chlorfenson, tetradifon, phenproxide, avermectins, clofentezine, flubenzimine, fenazaquin, pyridaben, fenproximate, chlorfenethol, thiophanate-methyl, benomyl, thiram, iprobenfos, edifenfos, fthalide, probenazole, isoprothiolane, chorothalonil, captan, polyoxin-B, blasticidin-S, kasugamycin, validamycin, tricyclazole, pyroquilon, phenazine oxide, mepronil, flutolanil, pencycuron, iprodione, hymexazole, metalaxyl, triflumizole, diclomezine, tecloftalam, vinclozolin, procymidone, bitertanol, triadimefon, prochloraz, pyrifenox, fenarimal, fenpropimorph, triforine, metalaxyl, oxycarboxin, pefrazoate, diclomedine, fluazinam, oxadixyl, ethoquinolac, TPTH, propamocarb, fosetyl, dihydrostreptomycin, anilazine, dithianon, diethofencarb. Organophosphorus-type and carbamate-type insecticides (acaridides): fenthion, fenitrothion, diazinon, chlorpyrifos, oxydeprofos, vamidothion, phenthoate, dimethoate, formothion, malathion, trichlorfon, thiometon, phosmet, menazon, dichlorvos, acephate, EPBP, dialifos, parathion-methyl, oxydemeton-methyl, ethion, aldicarb, propoxur, methomyl, fenobucarb, BPMC, pyraclofos, monocrotophos, salithion, cartap, carbosulfan, carbofuran, benfuracarb, metolcarb, carbaryl, pirimicarb, ethiofencarb, fenoxycarb, 
     Pyrethroide-type insecticides (acaricides): permethrin, cypermethrin, deltamethrin, fenvalerate, fenpropathrin, pyrethrins, allethrin, tetramethrin, resmethrin, parthrin, dimethrin, proparthrin, bifenthrin, prothrin, fluvalinate, cyhalothrin, cyhalothrin, flucythrinate, ethofenprox, cycloprothrin, tralomethrin, silaneophan. 
     Benzoylphenylurea-type and other types insecticides: 
     diflubenzuron, chlorfluazuron, triflumuron, teflubenzuron, buprofezin, pyriproxyfen, flufenoxuron, Machine oil. 
     Same examples of the formulations are given below. The carriers, surface-active agents, etc. that are added, however, are not limited to these Examples. 
     Example 7 
     Emulsifiable concentrate 
     
         ______________________________________The compound of this invention                10 partsAlkylphenyl polyoxyethylene                 5 partsDimethyl formamide   50 partsXylene               35 parts______________________________________ 
    
     These components are mixed and dissolved and, for use in spraying, the liquid mixture is water-diluted into an emulsion. 
     Example 8 
     Wettable powder 
     
         ______________________________________The compound of this invention                20 partsHigher alcohol sulfuric ester                 5 partsDiatomaceous earth   70 partsSilica                5 parts______________________________________ 
    
     These components are mixed and ground to fine powder, which for use in spraying, are water-diluted into a suspension. 
     Example 9 
     Dust 
     
         ______________________________________The compound of this invention                  5 partsTalc                 94.7 partsSilica                0.3 parts______________________________________ 
    
     These are mixed and ground and used as-ground in spraying. 
     Example 10 
     Granule 
     
         ______________________________________The compound of this invention                     5 partsClay                     73 partsBentonite                20 paratsSodium dioctylsulfosuccinate                     1 partSodium phosphate          1 part______________________________________ 
    
     The above compounds are granulated, and applied as it is when used. 
     Industrial applicability: 
     The tests below show the insecticidal activity of the compounds of this invention. 
     Test 1 Efficacy for cotton aphid 
     30 to 50 insects of cotton aphid per plot were inoculated using a small brush on cucumber leaves which were seeded in pots, 10 cm in diameter, and 10 days old after germination. A day later, wounded insect pests were removed, and a chemical solution, which was prepared in the way that the emulsifiable concentrate described in Example 7 of the above example of insecticide was diluted with water to 125 ppm of compound concentration according to the prescription, was sprayed. The pots were placed in a thermostatic room at temperature of 25 ° C. and humidity of 65%. The number of survival pests was counted 7 days later and the control efficacy was calculated by comparing with that of untreated plot. The results are shown in Table 2. 
     
                       TABLE 2______________________________________          Control Efficacy (7 days later)Compound No.   125 ppm______________________________________ 1              100% 2             100 3             100 4             100 6             100 8             10010             10016             10020             10021             10022             10023             10024             10025             10027             10029             10031             10032             10033             10038             10044             10048             10050             10051             10053             10057             10060             10062             10064             10066             10068             10070             10072             10073             10074             10078             10080             10082             10084             10086             10088             10092             10096             100100            100102            100115            100116            100120            100124            100130            100132            100136            100144            100145            100146            100148            100149            100150            100151            100152            100163            100164            100169            100170            100171            100172            100173            100174            100177            100178            100188            100189            100190            100194            100203            100206            100213            100236            100366            100368            100381            100383            100543            100Comparative compound A           27Comparative compound B          100______________________________________Comparative compound A: - ##STR510##Comparative compound B: ##STR511##  Test 2 Efficacy for green rice leafhopper 
    
     Rice seedlings of 7 days old after germination were immersed in a chemical solution, which was prepared in the way that the emulsifiable concentrate described in Example 7 of the above example of insecticide was diluted with water to 125 ppm of compound concentration according to prescription, for 30 seconds. After dried in air, the treated seedlings were placed in test tubes and 10 insects of 3rd-instar larvae of green rice leafhopper resistant to the organophosphorus and carbamate insecticides were inoculated. The tubes were covered with gauze, and placed in a thermostatic room at temperature of 25° C. and humidity of 65%. The mortality was checked 5 days later. The results are shown in Table 3. 
     
                       TABLE 3______________________________________            % mortality (5 days later)Compound No.     125 ppm______________________________________ 1                100% 2               100 4               100 6               100 8               10010               10016               10018               10020               10021               10022               10023               10024               10025               10027               10028               10029               10031               10032               10033               10035               10036               10044               10048               10050               10051               10053               10057               10060               10062               10066               10068               10072               10073               10074               10078               10082               10084               10086               10088               10092               10096               100100              100102              100116              100120              100124              100130              100132              100136              100144              100146              100148              100150              100152              100164              100169              100170              100171              100172              100173              100174              100178              100188              100190              100201              100203              100213              100236              100366              100368              100369              100381              100Comparative Compound A             0Comparative Compound B             0Comparative Compound C             0______________________________________Comparative compound A and B: The same as test 1Compound C: ##STR512##  Test 3 Efficacy for rice armyworm 
    
     The test compounds were formulated into the wettable powder in the same manner as Example 8. The compounds were diluted with water to 125 ppm. A maize leaf was immersed in the chemical solution for 30 seconds. After air-dried, the treated leaf was placed in a petri dish and five 3rd-instar larvae of rice armyworm were inoculated. The petri dishes were covered with glass lids, and placed in a thermostatic room at 25° C. and 65% relative humidity. The mortality was checked 5 days later. Two replications were conducted in the each test. The results are shown in Table 4. 
     
                       TABLE 4______________________________________            % mortality (5 days later)Compound No.     125 ppm______________________________________21                100%22               10023               10024               10025               10051               10057               10088               10092               100148              100172              100381              100Comparative compound A             0Comparative compound B             0Comparative compound D             40______________________________________Comparative compound A and B: The same as Test 1Compound D: ##STR513##