Herbicidal pyridine sulfonamides

TECHNICAL FIELD
This invention relates to certain novel pyridine sulfonamide compounds, to compositions containing such compounds, and to a method of use of such compositions to control the growth of undesired vegetation.
BACKGROUND OF THE INVENTION
The present of undesired vegetation causes substantial damage to agricultural products which helps satisfy man's basic food and fiber needs. The current population explosion and concomitant world food and fiber shortage demand improved productivity in agricultural efforts since virtually all the readily available, relatively fertile cropland in developed countries has already been placed in use [Science, 214, 1087, 1089 (1981)]. Preventing or minimizing loss of a portion of such valuable crops, by inhibiting the growth or killing undesired competing vegetation which is potentially most damaging to crop yields [Science 215, 134 (1982)], is a significant approach to improving agricultural efficiency.
A wide variety of materials, commonly referred to as herbicides, useful for controlling the growth of undesired vegetation (by killing or inhibiting) is available. There still exists a need, however, for effective herbicides which destroy or control weeds while not significantly damaging useful crops. Efficient production on large acreage requires the extensive use of herbicides used by American farmers in 1981 [Chemical Weed, July 7, 1982, p. 36]. At the present time, no existing product provides all features deemed advantageous. Greater persistence, less soil residual, reduced application rates, reduced soil binding, greater selectivity or safety margin between weed control and crop injury, and less dependence on rainfall for activation are currently desirable features for herbicides.
EP-A-No. 13,480 published July 23, 1980, discloses herbicidal sulfonamides of the formula ##STR1## wherein R.sub.1 is H, Cl, Br, F, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, NO.sub.2 or CO.sub.2 R.sub.5.
U.S. Pat. No. 4,339,267 discloses herbicidal sulfonamides of the formula ##STR2## wherein R.sub.4 is H, Cl, Br, F, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, NO.sub.2, CO.sub.2 R.sub.6 or SR.sub.13.
U.S. Pat. No. 4,342,587 discloses herbicidal sulfonamides of the formula ##STR3## wherein B is Cl or Br.
U.S. Pat. No. 4,456,469 discloses herbicidal sulfonamides of the formula ##STR4## wherein R is C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.5 -C.sub.6 cycloalkyl, R'OCH.sub.2 CH.sub.2 OCH.sub.2, R'OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2, ##STR5## CF.sub.3, CF.sub.3 CH.sub.2, HGLCCF.sub.2 or HCF.sub.2 ; and Z is H, F, Cl, Br, CH.sub.3, OCH.sub.3 or SCH.sub.3.
U.S. Pat. No. 4,487,626 discloses herbicidal sulfonamides of the formula ##STR6## wherein A is ##STR7## and R.sub.2 is H, F, Cl, Br, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, NO.sub.2, CO.sub.2 R.sub.15, S(O).sub.m R.sub.16, SO.sub.2 NR.sub.18 R.sub.19 or SO.sub.2 N(OCH.sub.3)CH.sub.3.
U.S. Pat. No. 4,421,550 discloses herbicidal sulfonamides of the formula ##STR8## wherein Z is ##STR9## and R.sub.16 is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, F, Cl, Br, CF.sub.3, CO.sub.2 R.sub.20, SO.sub.2 NR.sub.10 R.sub.11, SO.sub.2 N(OCH.sub.3)CH.sub.3 or S(O).sub.n R.sub.13.
U.S. Pat. No. 4,496,392 discloses herbicidal sulfonamides of the formula ##STR10## wherein R is Cl, SO.sub.2 CH.sub.3 or SO.sub.2 N(CH.sub.3).sub.2.
EP-A-No. 84,224, published July 27, 1983, discloses herbicidal sulfonamides of the formula ##STR11## wherein A is ##STR12## and R.sub.16 is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, F, Cl, Br, CF.sub.3, CO.sub.2 R.sub.9, SO.sub.2 NR.sub.10 R.sub.11, SO.sub.2 N(OCH.sub.3)CH.sub.3 or S(O).sub.n R.sub.13.
EP-A-No. 125,846, published Nov. 21, 1984, discloses herbicidal sulfonamides of the formula ##STR13## wherein J is ##STR14## and R.sub.3 is Cl, SO.sub.2 CH.sub.3, SO.sub.2 N(CH.sub.3).sub.2, OCH.sub.3, NO.sub.2 or N(CH.sub.3).sub.2.
EP-A-No. 155,767, published Sept. 25, 1985, discloses herbicidal sulfonamides of the formula ##STR15## wherein J is ##STR16## and R.sub.5 is H, CH.sub.3, Cl, Br, CO.sub.2 R.sub.15, C(O)NR.sub.16 R.sub.17, SO.sub.2 NR.sub.16 R.sub.17, SO.sub.2 N(OCH.sub.3)CH.sub.3, SO.sub.2 R.sub.18 or NO.sub.2.
EP-A-No. 161,905, published Nov. 21, 1985, discloses herbicidal sulfonamides of the formula ##STR17## wherein R.sub.4 is CH.sub.3, CH.sub.2 CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, F, Cl, Br, SO.sub.2 NR.sub.16 R.sub.17, SO.sub.2 N(OCH.sub.3)CH.sub.3, S(O).sub.n R.sub.19, C.sub.3 -C.sub.4 alkenyloxy or C.sub.3 -C.sub.4 alkynyloxy.
EP-A-No. 164,269, published Dec. 11, 1985, discloses herbicidal sulfonamides of the formula ##STR18## wherein R.sub.4 is CH.sub.3, CH.sub.2 CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, F, Cl, Br, SO.sub.2 NR.sub.11 R.sub.12, SO.sub.2 N(OCH.sub.3)CH.sub.3 or S(O).sub.n R.sub.13.
EP-A-No. 171,286, published Feb. 12, 1986, discloses herbicidal sulfonamides of the formula ##STR19## wherein R.sub.4 is CH.sub.3, CH.sub.2 CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, F, Cl, Br, SO.sub.2 NR.sub.18 R.sub.19, SO.sub.2 N(OCH.sub.3)CH.sub.3, S(O).sub.n R.sub.21, C.sub.3 -C.sub.4 alkenyloxy, CH.sub.2 OCH.sub.3 or CH.sub.2 OCH.sub.2 CH.sub.3.
EP-A-No. 187,489, published July 16, 1986, discloses herbicidal sulfonamides of the formula ##STR20## wherein L is ##STR21## Q is an optionally substituted 3- or 4-membered ring; and W is substituted alkenyl or alkynyl.
AU-A-No. 24259/84, published Sept. 6, 1984, discloses herbicidal guanidines of the formula ##STR22## wherein R.sub.26 and R.sub.27 are independently H, F, Cl, Br, NO.sub.2, CN, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 haloalkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 haloalkylsulfonyl, di-(C.sub.1 -C.sub.4 alkyl)aminosulfonyl or C.sub.1 -C.sub.4 alkoxy carbonyl.
EP-A-No. 117,014, published Aug. 29, 1984, discloses herbicidal quanidines of the formula ##STR23## wherein R.sub.8 is CH.sub.3, CH.sub.2 CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, F, Cl, Br, SO.sub.2 NR.sub.20 R.sub.21, SO.sub.2 N(OCH.sub.3)CH.sub.3 or S(O).sub.n R.sub.23.
JAP No. 62-111,982, published May 22, 1987, discloses herbicidal pyridine sulfonylureas containing a ortho-CH.sub.2 OR.sub.1 group, wherein R.sub.1 is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl.
SUMMARY OF THE INVENTION
The novel pyridine sulfonamide compounds of the present invention are highly active as preemergent and/or postemergent herbicides or plant growth regulants. Specifically, one aspect of the invention relates to compounds having the formula I: ##STR24## wherein J is ##STR25## R is H or CH.sub.3 ; E is a single bond or CH.sub.2 ;
W is O, S or NR.sub.x ;
p is 0 or 1;
R.sub.x is H, OH, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkoxy, allyloxy, propargyloxy or NR.sub.x R.sub.z ;
R.sub.y is H or C.sub.1 -C.sub.3 alkyl;
R.sub.z is C.sub.1 -C.sub.3 alkyl;
R.sub.1 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, halogen, nitro, C.sub.1 -C.sub.3 alkoxy, SO.sub.2 NR.sub.a R.sub.b, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfanyl, CN, CO.sub.2 R.sub.c, C.sub.1 -C.sub.3 haloalkoxy, C.sub.1 -C.sub.3 haloalkylthio, amino, C.sub.1 -C.sub.2 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, L or C(O)NR.sub.d R.sub.e ;
R.sub.a is H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.3 cyanoalkyl, methoxy or ethoxy;
R.sub.b is H, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.4 alkenyl; or
R.sub.a and R.sub.b may be taken together as --(CH.sub.2).sub.3, --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --;
R.sub.c is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.3 alkynyl, C.sub.2 -C.sub.4 haloalkyl, C.sub.1 -C.sub.2 cyanoalkyl, C.sub.5 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl or C.sub.2 -C.sub.4 alkoxyalkyl;
R.sub.d is H or C.sub.1 -C.sub.3 alkyl;
R.sub.e is C.sub.1 -C.sub.3 alkyl;
L is ##STR26## Q is C.sub.1 -C.sub.4 alkyl substituted with R.sub.2 ; R.sub.2 is OR.sub.3, S(O).sub.n R.sub.4, CO.sub.2 R.sub.4 ', CONR.sub.5 R.sub.6, ##STR27## R.sub.3 is H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.4 haloalkenyl, C.sub.3 -C.sub.4 haloalkynyl, C.sub.2 -C.sub.4 alkylcarbonyl, C.sub.2 -C.sub.4 haloalkylcarbonyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.2 -C.sub.4 alkylthioalkyl or C.sub.2 -C.sub.4 cyanoalkyl;
R.sub.4 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.4 haloalkenyl, C.sub.3 -C.sub.4 haloalkynyl, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.2 -C.sub.4 alkylthioalkyl or C.sub.2 -C.sub.4 cyanoalkyl;
R.sub.4 ' is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 haloalkyl, C.sub.3 -C.sub.4 haloalkenyl, C.sub.3 -C.sub.4 haloalkynyl, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.2 -C.sub.4 alkylthioalkyl or C.sub.2 -C.sub.4 cyanoalkyl;
R.sub.5 is H or C.sub.1 -C.sub.3 alkyl;
R.sub.6 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, cyclopropyl, allyl or propargyl;
R.sub.5 and R.sub.6 may be taken together to form --CH.sub.2 --.sub.3, --CH.sub.2 --.sub.4, --CH.sub.2 --.sub.5 or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --;
R.sub.7 is H, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl;
R.sub.7 ' is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, Cl or CN;
R.sub.8 is C.sub.1 -C.sub.2 alkyl;
R.sub.9 is H or CH.sub.3 ;
R.sub.10 is H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl or C.sub.3 -C.sub.4 alkynyl;
R.sub.11 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylamino or di(C.sub.1 -C.sub.4 alkyl)amino;
W.sub.1 is O or S;
n is 0, 1 or 2;
m is 1 or 2;
R.sub.12 is H or CH.sub.3 ;
R.sub.13 is H or CH.sub.3 ;
R.sub.14 and R.sub.15 are independently C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, NHCH.sub.3 or N(CH.sub.3).sub.2 ;
A is ##STR28## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino or di(C.sub.1 -C.sub.3 alkyl)amino;
Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylthioalkyl, C.sub.2 -C.sub.5 alkylsulfinylalkyl, C.sub.2 -C.sub.5 alkylsulfonylalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkynyl, C.sub.3 -C.sub.5 cycloalkyl, azido, cyano, ##STR29## or N(OCH.sub.3)CH.sub.3 ; i is 2 or 3;
Q.sub.1 and Q.sub.2 are independently O or S;
R.sub.f is H or C.sub.1 -C.sub.3 alkyl;
R.sub.g and R.sub.h are independently C.sub.1 -C.sub.3 alkyl;
Z is CH, N, CCH.sub.3, CC.sub.2 H.sub.5, CCl or CBr;
Y.sub.1 is O or CH.sub.2 ;
X.sub.1 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or OCF.sub.2 H;
X.sub.2 is CH.sub.3, C.sub.2 H.sub.5 or CH.sub.2 CF.sub.3 ;
Y.sub.2 is OCH.sub.3, OC.sub.2 H.sub.5, SCH.sub.3, SC.sub.2 H.sub.5, CH.sub.3 or CH.sub.2 CH.sub.3 ;
X.sub.3 is CH.sub.3 or OCH.sub.3 ;
Y.sub.3 is H or CH.sub.3 ;
X.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3 or Cl;
Y.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or Cl;
and their agriculturally suitable salts; provided that
(1) when X is halogen, then Z is CH and Y is OCH.sub.3, OC.sub.2 H.sub.5, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, OCF.sub.2 H, OCF.sub.2 Br or N(OCH.sub.3)CH.sub.3 ;
(2) when X or Y is C.sub.1 haloalkoxy, then Z is CH;
(3) when W is S, then R is H, E is a single bond, A is A-1, Z is CH or N, and Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, C.sub.2 H.sub.5, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2 or ##STR30## (4) when the total number of carbon atoms of X and Y is greater than four, then the combined number of carbons of R.sub.1 and Q is less than or equal to six;
(5) X.sub.4 and Y.sub.4 are not simultaneously Cl;
(6) when Y is CN then Q is other than CH.sub.2 OCH.sub.3 or CH.sub.2 OCH.sub.2 CH.sub.3 ; and
(7) when Y is C.sub.2 -C.sub.4 alkynyl then Q is other than CH.sub.2 OCH.sub.3 or CH.sub.2 OCH.sub.2 CH.sub.3 ;
Another aspect of this invention relates to a composition suitable for controlling the growth of undesired vegetation which comprises a herbicidally effective amount of a compound or the compounds of formula I and a diluent, surfactant, or mixture thereof. Yet another aspect of the invention relates to a method for the control of undesired vegetation which comprises applying to the locus of the undesired vegetation a herbicidally effective amount of the compounds of formula I.
Preferred compounds for reasons of increased ease of synthesis and/or greater herbicidal efficacy are:
(1) Compounds of Formula I where when J is J-1, R.sub.1 is H, Q is CH.sub.2 OR.sub.3 and both of X and Y are selected from CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or halogen; then R.sub.3 is other than C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl.
(2) Compounds of Preferred 1 where
X is C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, Cl, F, Br, I, OCF.sub.2 H, CH.sub.2 F, CF.sub.3, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, CH.sub.2 Cl or CH.sub.2 Br; and
Y is H, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.2 CH.sub.3, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, C(O)R.sub.f, ##STR31## SCF.sub.2 H, OCF.sub.2 Br, cyclopropyl, C.tbd.CH or C.tbd.CCH.sub.3 ; and Z is CH or N.
(3) Compounds of Preferred 2 where
E is a single bond;
W is O.
(4) Compounds of Preferred 3 where
R.sub.1 is H, CH.sub.3, C.sub.1 haloalkyl, halogen, NO.sub.2, OCH.sub.3, SO.sub.2 N(CH.sub.3).sub.2, SCH.sub.3, S(O)CH.sub.3, SO.sub.2 CH.sub.3, CO.sub.2 R.sub.c, C.sub.1 haloalkoxy, C.sub.1 haloalkylthio, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, N(CH.sub.3)CH.sub.2 CH.sub.3 or CON(CH.sub.3).sub.2 ;
R.sub.c is C.sub.1 -C.sub.3 alkyl, allyl, propargyl, CH.sub.2 CH.sub.2 OCH.sub.3 or CH.sub.2 CH.sub.2 Cl;
Q is C.sub.1 -C.sub.2 alkyl substituted with R.sub.2 ;
R.sub.2 is OR.sub.3, S(O).sub.n R.sub.4, CO.sub.2 R.sub.4 ', CONR.sub.5 R.sub.6 ; ##STR32## or CN; R.sub.3 is H, C.sub.1 -C.sub.2 alkyl, allyl, propargyl, C.sub.1 -C.sub.2 haloalkyl, C.sub.2 -C.sub.3 alkylcarbonyl or SO.sub.2 CH.sub.3 ;
R.sub.4 is C.sub.1 -C.sub.2 alkyl, allyl, propargyl, C.sub.1 -C.sub.2 haloalkyl or C.sub.2 -C.sub.3 alkoxycarbonyl;
R.sub.4 ' is C.sub.1 -C.sub.2 alkyl, allyl, propargyl, C.sub.2 haloalkyl or CH.sub.2 CH.sub.2 OCH.sub.3 ;
R.sub.5 is H or CH.sub.3 ;
R.sub.6 is C.sub.1 -C.sub.2 alkyl;
R.sub.7 is H or CH.sub.3 ;
R.sub.7 ' is H or CH.sub.3 ;
R.sub.10 is CH.sub.3 or CH.sub.2 CH.sub.3 ; and
R.sub.g is H or CH.sub.3.
(5) Compounds of Preferred 4 where J is J-1.
(6) Compounds of Preferred 4 where J is J-2.
(7) Compounds of Preferred 4 where J is J-3.
(8) Compounds of Preferred 4 where J is J-4.
(9) Compounds of Preferred 8 where
p is 0;
R is H;
A is A-1;
X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, Cl, OCF.sub.2 H or OCH.sub.2 CF.sub.3 ; and
Y is CH.sub.3, OCH.sub.3, C.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3 or CH(OCH.sub.3).sub.2.
(10) Compounds of Preferred 5 where
p is 0;
R is H;
A is A-1;
X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, Cl, OCF.sub.2 H or OCH.sub.2 CF.sub.3 ; and
Y is CH.sub.3, OCH.sub.3, C.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3 or CH(OCH.sub.3).sub.2.
(11) Compounds of Preferred 6 where
p is 0;
R is H;
A is A-1;
X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, Cl, OCF.sub.2 H or OCH.sub.2 CF.sub.3 ; and
Y is CH.sub.3, OCH.sub.3, C.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3 or CH(OCH.sub.3).sub.2.
(12) Compounds of Preferred 7 where
p is 0;
R is H;
A is A-1;
X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, Cl, OCF.sub.2 H or OCH.sub.2 CF.sub.3 ; and
Y is CH.sub.3, OCH.sub.3, C.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3 or CH(OCH.sub.3).sub.2.
(13) Compounds of Formula I wherein
J is J-1;
R.sub.1 is H;
Q is CH.sub.2 OR.sub.3 ;
R.sub.3 is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl.
Specifically preferred for reasons of greatest ease of synthesis and/or greatest herbicidal efficacy are N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-(methylthiomethyl)-2-pyridinesulfonamide, m.p. 145.degree.-147.degree. C.; and N-[(4-chloro-6-methoxypyrimidin-2-yl)aminocarbonyl]-3-(methylthiomethyl)-2-pyridine sulfonamide, m.p. 145.degree.-147.degree. C.
In the above definitions, the term "alkyl", used either alone or in compound words such as "alkylthio" or "haloalkyl", denotes straight chain or branched alkyl, e.g., methyl, ethyl, n-propyl, isopropyl or the different butyl isomers.
Alkoxy denotes methoxy, ethoxy, n-propoxy, isopropoxy and the different butoxy isomers.
Alkenyl denotes straight chain or branched alkenes, e.g., 1-propenyl, 2-propenyl, 3-propenyl and the different butenyl isomers.
Alkynyl denotes straight chain or branched alkynes, e.g., ethynyl, 1-propynyl, 2-propynyl and the different butynyl isomers.
Cycloalkyl denotes cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
The term "halogen", either alone or in compound words such as "haloalkyl", denote fluorine, chlorine, bromine or iodine. Further, when used in compound words such as "haloalkyl" said alkyl may be monohalogenated or fully substituted with halogen atoms, which may be the same or different. Examples of haloalkyl include CH.sub.2 CH.sub.2 F, CF.sub.2 CF.sub.3 and CH.sub.2 CHFCl. Similarly, haloalkenyl, haloalkoxy and halothioalkyl would be said to include compounds which were monosubstituted or polysubstituted by halogen atoms, which may be the same or different.
The total number of carbon atoms in a substituent group is indicated by the C.sub.i -C.sub.j prefix where i and j are numbers from 1 to 5. For example, C.sub.1 -C.sub.3 alkylsulfonyl would designate methylsulfonyl through propylsulfonyl, C.sub.2 alkoxyalkoxy would designate OCH.sub.2 OCH.sub.3 ; C.sub.4 alkoxyalkoxy would designate the various isomers of an alkoxy group substituted with a second alkoxy group containing a total of 4 carbon atoms, examples including OCH.sub.2 OCH.sub.2 CH.sub.2 CH.sub.3 and OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 ; as a further example C.sub.2 cyanoalkyl would designate CH.sub.2 CN and C.sub.3 cyanoalkyl would designate CH.sub.2 CH.sub.2 CN and CH(CN)CH.sub.3.
DETAILED DESCRIPTION OF THE INVENTION
Synthesis
Compounds of Formula I can be prepared by the methods described in Equations 1 and 2. ##STR33##
The reaction shown in Equation 1 is carried out by contacting the phenyl carbamate of Formula (3) with the aminoheterocycle of Formula (2) in an inert organic solvent such as dioxane or tetrahydrofuran at temperatures of about 20.degree. to 100.degree. C. for a period of about one-half to twenty-four hours. The product can be isolated by evaporation of the reaction solvent and purified by trituration of the evaporation residue with solvents such as 1-chlorobutane or ethyl ether and filtration, by recrystallization from mixtures of solvents such as 1,2-dichloroethane, 1-chlorobutane and heptane or by chromatography on silica gel.
The phenyl carbamates of Formula (3) can be prepared by the methods described (or modifications thereof) in EPO No. 44,808 or South African Patent Application No. 825042. ##STR34##
The reaction of Equation 2 can be carried out by contacting equimolar amounts of the sulfonamide of Formula (4) with a heterocyclic phenyl carbamate of Formula (5) in the presence of an equimolar amount of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), by methods analogous to those described in South African Patent Application No. 830441. The phenyl carbamates of Formula (5) can be prepared by methods (or modifications thereof) described in South African Patent Application No. 825671 and South African Patent Application No. 825045.
The sulfonamide (4) can be prepared via the routes shown in Equations 3, 4 and 5 or by modifications thereof. ##STR35## where X is F, Br, Cl.
The halopyridine (6) (The Chemistry of Heterocyclic Compounds, Vol. 14, Wiley-Interscience, New York (1964)) is added to a solution of sodium benzylthiolate in dimethylformamide and stirred for 12 to 24 hours. The mixture is partitioned between water and ether. The ether phase is washed with brine, dried over sodium sulfate and filtered. Evaporation of the ether leaves sulfide (7) (Equation 3a).
The compound (7) is converted to the sulfonamide (8) with hypochlorite solution as described in South African Patent Application No. 848845 (Equation 3b).
To a solution of (8) in an aprotic solvent such as tetrahydrofuran at -75.degree. to -80.degree. is added at least two equivalents of n-butyl lithium, the mixture is stirred at -78.degree. for 30 to 60 minutes, followed by addition of chloromethyl methyl ether. The reaction mixture is quenched with brine, extracted with methylene chloride, dried over sodium sulfate, and concentrated to leave ether (9) (Equation 3c).
A solution of ether (9) and trifluoroacetic acid is stirred at 25.degree. to 40.degree. for one to two days and then concentrated to leave sulfonamide (4). ##STR36##
The hydroxypyridine (10) (The Chemistry of Heterocyclic Compounds, Vol. 14, Wiley-Interscience, New York (1964)) is converted to mercaptopyridine (11) via the thiocarbamate according to the procedure of Newman et al. in J. Org. Chem. 1966, 31, 3980 (Equation 4a).
Mercaptopyridine (11) is converted to sulfonamide (12) as described previously in Equation 3b (Equation 4b).
A solution of N-bromosuccinimide, benzoyl-peroxide, and sulfonamide (12) in carbon tetrachloride is refluxed for four to twenty-four hours according to the procedures of Camirez et al. (J. Org. Chem. 1954, 19, 183). The cooled solution is filtered and the filtrate is concentrated to leave bromide (13) (Equation 4c).
Bromide (13) is contacted with a solution of potassium cyanide in a water-methanol mixture and refluxed for 10 to 60 minutes using the procedure of Tessieri et al. in J. Org. Chem. 1954, 19, 711. The reaction mixture is cooled, and diluted with a saturated solution of sodium carbonate. The mixture is extracted with ether, dried over sodium sulfate and concentrated to leave cyanomethyl (14) (Equation 4d).
Compound (14) is treated with trifluoroacetic acid as described previously in Equation 3d to yield sulfonamide (4) (Equation 4e). ##STR37##
The 3-aminopyridine (15) (The Chemistry of Heterocyclic Compounds, Vol. 14, Wiley-Interscience, New York (1964)) is diazotized and contacted with potassium ethyl xanthate according to the procedure of Katz et al. in J. Amer. Chem. Soc. 1951, 73, 4925 to give disulfide (16) (Equation 5a).
Esterification of (16) using thionyl chloride, pyridine and methanol (ibid.), is followed by the oxidation of the disulfide using the procedure previously described in Equation 3b (Equation 5b and 5c).
The ester (18) is dissolved in ether and added to a solution of lithium aluminum hydride in ether. The mixture is stirred for 15 to 60 minutes and ethanol is added to decompose the excess lithium aluminum hydride. The mixture is filtered and the ether filtrate is concentrated to an oil. This oil is treated with 10% sodium hydroxide and continuously extracted with ether. The ether extracts are concentrated to leave alcohol (4).
The heterocyclic amines of Formula (2) are known compounds. ##STR38##
The synthesis of heterocyclic amines such as those represented by Formula 2 has been reviewed in "The Chemistry of Heterocyclic Compounds," a series published by Interscience Publ., New York and London. Aminopyrimidines are described by D. J. Brown in "The Pyrimidines," Vol. XVI of the series mentioned above which is herein incorporated by reference. The 2-amino-1,3,5-triazines of Formula 2, where A is A-1 and Z is N, can be prepared according to the methods described by E. M. Smolin and L. Rapaport in "s-Triazines and Derivatives," Vol. XIII.
Pyrimidines of Formula 2, where A is A-1 and Y is an acetal or thioacetal substituent, can be prepared by methods taught in European Patent Application No. 84,224 (published July 27, 1983).
Pyrimidines of Formula 2, where A is A-1 and Y is cyclopropyl or OCF.sub.2 H can be synthesized according to the methods taught in U.S. Pat. No. 4,515,626 and U.S. Pat. No. 4,540,782, respectively.
Compounds of Formula 2, where A is A-2 or A-3, can be prepared by procedures disclosed in U.S. Pat. No. 4,339,267.
Compounds of Formula 2, where A is A-4, can be prepared by methods taught in U.S. Pat. No. 4,487,626.
Additional reference dealing with the synthesis of bicyclic pyrimidines of Formula 2, where A is A-2, A-3, or A-4 are Braker, Sheehan, Spitzmiller and Lott, J. Am. Chem. Soc., 69, 3072 (1947); Mitler and Bhattachanya, Quart. J. Indian Chem. Soc., 4, 152 (1927); Shrage and Hitchings, J. Org. Chem., 16, 1153 (1951); Caldwell, Kornfeld and Donnell, J. Am. Chem. Soc., 63, 2188 (1941); and Fissekis, Myles and Brown, J. Org. Chem., 29, 2670 (1964).
Compounds of Formula 2, where A is A-5, can be prepared by methods taught in U.S. Pat. No. 4,421,550.
Compounds of Formula 2, where A is A-6, can be prepared by methods taught in U.S. Pat. No. 4,496,392.
Compounds of Formula 2, where A is A-7, can be prepared by methods taught in EP-A-No. 125,864.
Agriculturally suitable salts of compounds of Formula I are also useful herbicides and can be prepared by well-known methods including those described in U.S. Pat. No. 4,127,405.
The following Example illustrates syntheses of the compounds of this invention. Temperatures are in degrees Celsius.

EXAMPLE 1
Step A. 3-Methyl-2-(phenylmethylthio)-pyridine
A suspension of 4.8 g (100 mmole) of sodium hydride in 50 mls of dimethylformamide was cooled to 0.degree. and 11.6 ml (100 mmole) of benzyl mercaptan was added dropwise at 0.degree.. After addition was complete, the reaction mixture was allowed to warm to 25.degree. and stirred at this temperature for 1 hour. The reaction mixture was then re-cooled to 0.degree. and 10.0 g (91 mmole) of 2-fluoro-3-methyl pyridine was added dropwise. The mixture was allowed to warm to 25.degree. and stirred at this temperature for 18 hours. The mixture was poured into 100 mls of water and extracted twice with ethyl ether and ethylacetate. The combined organic extracts were washed with a saturated solution of sodium bicarbonate and dried over sodium sulfate. Concentration gave 24 g of a yellow oil. Flash chromatography in a 10% ethyl ether/hexanes mixture gave 6.3 g clear oil.
NMR (CDCl.sub.3) 2.25 (s, 3H, CH.sub.3),
4.52 (s, 2H, SCH.sub.2 C.sub.6 H.sub.5),
6.95 (dd, 1H),
7.30 (m, 4H),
7.48 (m, 2H),
8.34 (dd, 1H).
Step B. N-(1,1-dimethylethyl)-3-methyl-2-pyridinesulfonamide
A mixture of 45 mls of concentrated hydrochloric acid, 500 mls of methylene chloride, 260 ml of water, and 25.0 g (116 mmole) of 3-methyl-2-(phenylmethylthio)pyridine was cooled to 0.degree.. Maintaining a temperature of -5.degree. to 0.degree., 500 mls (338 mmole) of 5% sodium hypochlorite was added dropwise. The resulting yellow emulsion was stirred at 0.degree. an additional 30 minutes. The reaction mixture was then extracted with methylene chloride and dried over sodium sulfate. The solution was filtered into a reaction flask and cooled to -78.degree. and 50 mls (476 mmole) of t-butyl amine added. The reaction mixture was allowed to warm to room temperature, poured into water, and extracted with methylene chloride. The solution was dried over sodium sulfate and concentrated to a brown oil. The resulting oil was triturated with ethyl ether and hexane to yield 10 g of tan solid, m.p. 107-110.
NMR (CDCl.sub.3) 1.27 (s, 9H, C(CH.sub.3).sub.3),
2.68 (s, 3H, CH.sub.3),
5.14 (s, 1H),
7.34 (m, 1H),
7.66 (dd, 1H),
8.46 (dd, 1H).
Step C. N-(1,1-dimethylethyl)-3-(methylthiomethyl)-2-pyridine-sulfonamide
A solution of 5.0 g (21.9 mmole) of the 3-methyl-2-(1,1-dimethyl-2-(1, 1-dimethylethyl)aminosulfonyl-pyridine in 50 mls of tetrahydrofuran was cooled to -78.degree. and 52 mls (67.6 mmole) of 1.3M n-butyllithium was added. After addition was complete, the reaction mixture was stirred at this temperature for 20 minutes, then 7.3 mls (81.0 mmole) of dimethyl disulfide was added dropwise at -78.degree.. The reaction mixture was quenched with brine, extracted with methylene chloride and the combined organic extracts were dried over sodium sulfate. Concentration gave a yellow oil. Flash chromatography in a 20% ethyl acetate/hexanes mixture gave 2.3 g solid, m.p. 89-92.
NMR (CDCl.sub.3) 1.27 (s, 9H, C(CH.sub.3).sub.3),
2.08 (s, 3H, SCH.sub.3),
4.20 (s, 2H, CH.sub.2 S)),
5.34 (s, 1H),
7.45 (dd, 1H),
7.93 (dd, 1H),
8.55 (dd, 1H).
Step D. 3-(Methylthiomethyl)-2-pyridinesulfonamide
A solution of 2.1 g (7.7 mmole) in 35 mls trifluoroacetic acid was stirred at room temperature for 24 hours and then warmed to 40.degree. for 24 hours. The trifluoroacetic acid was removed under vacuum. The resulting brown oil was triturated with n-butylchloride to yield 0.75 g solid, m.p. 68-70.
NMR (CDCl.sub.3) 2.06 (s, 3H, SCH.sub.3),
4.17 (s, 2H, SCH.sub.2),
5.55 (s, 2H),
7.49 (dd, 1H),
7.98 (dd, 1H),
8.53 (dd, 1H).
Step E. 2-[[(4,6-dimethoxypyrimidin-2-yl)amino-carbonyl]aminosulfonyl]-3-methylthiomethyl-pyridine
To a suspension of 0.18 g (0.82 mmole) 3-(methyl-thiomethyl)-2-aminosulfonylpyridine and 0.227 g (0.82 mmole) of 4,6-dimethoxypyrimidin-2-yl phenyl carbamate in 3 mls acetonitrile was added 0.126 mls (0.82 mmole) of 1,8-diazabicyclo[5.4.0]undec-7-ene. The resulting solution was stirred at room temperature for 5 minutes. The addition of 2 mls of water, followed by the dropwise addition of 10% hydrochloric acid produced a white precipitate which was collected by filtration to provide 0.270 g of the subject compound, m.p. 145.degree.-147.degree..
NMR (CDCl.sub.3) 2.09 (s, 3H, SCH.sub.3),
3.50 (s, 6H, OCH.sub.3),
4.27 (s, 2H, SCH.sub.2),
5.80 (s, 1H),
7.33 (s, 1H),
7.49 (dd, 1H),
8.10 (d, 1H),
8.50 (d, 1H),
12.83 (s, 1H).
Using these methods and those described in Equations 1-5, the compounds of Tables 1-14 can be prepared.
TABLE 1__________________________________________________________________________ ##STR39##R.sub.1 Q R Z X Y m.p. (.degree.C.)__________________________________________________________________________H CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3H CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.3 H CH CH.sub.3 C.sub.2 H.sub.5H CH.sub.2 OCH.sub.3 H CH CH.sub.3 NHCH.sub.3H CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.2 OCH.sub.3H CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH(OCH.sub.3).sub.2H CH.sub.2 OCH.sub.3 H CH OCH.sub.3 CH.sub.2 OCH.sub.3H CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3 163-168H CH.sub.2 OCH.sub.3 H CH OCH.sub.3 C.sub.2 H.sub.5H CH.sub.2 OCH.sub.3 H CH OCH.sub.3 NHCH.sub.3H CH.sub.2 OCH.sub.3 H CH OCH.sub.3 CH(OCH.sub.3).sub.2H CH.sub.2 OCH.sub.3 H CH OCH.sub.2 CH.sub.3 CH.sub.3H CH.sub.2 OCH.sub.3 H CH OCH.sub.2 CH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.3 H CH OCH.sub.2 CH.sub.3 C.sub.2 H.sub.5H CH.sub.2 OCH.sub.3 H CH OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 OCH.sub.3 H CH OCH.sub.2 CH.sub.3 CH.sub.2 OCH.sub.3H CH.sub.2 OCH.sub.3 H CH OCH.sub.2 CH.sub.3 CH(OCH.sub.3).sub.2H CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3 149-150H CH.sub.2 OCH.sub.3 H CH Cl NHCH.sub.3H CH.sub.2 OCH.sub.3 H CH OCF.sub.2 H CH.sub.3H CH.sub.2 OCH.sub.3 H CH OCF.sub.2 H OCH.sub.3H CH.sub.2 OCH.sub.3 H CH OCF.sub.2 H C.sub.2 H.sub.5H CH.sub.2 OCH.sub.3 H CH OCF.sub.2 H NHCH.sub.3H CH.sub.2 OCH.sub.3 H CH OCF.sub.2 H CH.sub.2 OCH.sub.3H CH.sub.2 OCH.sub. 3 H CH OCF.sub.2 H CH(OCH.sub.3).sub.2H CH.sub.2 OCH.sub.3 H CH CH.sub.2 CF.sub.3 CH.sub.3H CH.sub.2 OCH.sub.3 H CH CH.sub.2 CF.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.3 H CH CH.sub.2 CF.sub.3 C.sub.2 H.sub.5H CH.sub.2 OCH.sub.3 H CH CH.sub.2 CF.sub.3 NHCH.sub.3H CH.sub.2 OCH.sub.3 H CH CH.sub.2 CF.sub.3 CH.sub.2 OCH.sub.3H CH.sub.2 OCH.sub.3 H CH CH.sub.2 CF.sub.3 CH(OCH.sub.3).sub.2H CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3H CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3 139-141H CH.sub.2 OCH.sub.3 H N CH.sub.3 C.sub.2 H.sub.5H CH.sub.2 OCH.sub.3 H N CH.sub.3 NHCH.sub.3H CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.2 OCH.sub.3H CH.sub.2 OCH.sub.3 H N OCH.sub.3 CH(OCH.sub.3).sub.2H CH.sub.2 OCH.sub.3 H N OCH.sub.3 CH.sub.2 OCH.sub.3H CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3 158-160H CH.sub.2 OCH.sub.3 H N OCH.sub.3 C.sub.2 H.sub.5H CH.sub.2 OCH.sub.3 H N OCH.sub.3 NHCH.sub.3H CH.sub.2 OCH.sub.3 H N OCH.sub.3 CH(OCH.sub.3).sub.2H CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 CH.sub.3H CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 C.sub.2 H.sub.5H CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3 156-158H CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 CH.sub.2 OCH.sub.3H CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 CH(OCH.sub.3).sub.2H CH.sub.2 OCH.sub.3 H N CH.sub.2 CF.sub.3 CH.sub.3H CH.sub.2 OCH.sub.3 H N CH.sub.2 CF.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.3 H N CH.sub.2 CF.sub.3 C.sub.2 H.sub.5H CH.sub.2 OCH.sub.3 H N CH.sub.2 CF.sub.3 NHCH.sub.3H CH.sub.2 OCH.sub.3 H N CH.sub.2 CF.sub.3 CH.sub.2 OCH.sub.3H CH.sub.2 OCH.sub.3 H N CH.sub.2 CF.sub.3 CH.sub.2 (OCH.sub. 3).sub.2CH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3CH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3CH.sub.3 CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3CH.sub.3 CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3CH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3CH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3CH.sub.3 CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3CH.sub.3 CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3CH.sub.2 Cl CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3CH.sub.2 Cl CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3CH.sub.2 Br CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3CH.sub.2 Br CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3CH.sub.2 F CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3CH.sub.2 F CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3CH.sub.2 I CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3CH.sub.2 I CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3F CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3F CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3F CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3F CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3F CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3F CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3F CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3F CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3Cl CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3 165-169Cl CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3 138-142Cl CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3 161-164Cl CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3Cl CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3 130-135Cl CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3 135-140Cl CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3 136-142Cl CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3 168-171Cl CH.sub.2 OCH.sub. 3 CH.sub.3 N OCH.sub.3 CH.sub.3 121-124Cl CH.sub.2 OCH.sub.3 CH.sub.3 CH OCH.sub.3 OCH.sub.3 130-134Br CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3Br CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3Br CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3Br CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3Br CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3Br CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3Br CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3Br CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3I CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3I CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3NO.sub.2 CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3NO.sub.2 CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3NO.sub.2 CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3NO.sub.2 CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3NO.sub.2 CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3NO.sub.2 CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3NO.sub.2 CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3NO.sub.2 CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3SO.sub.2 N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3SO.sub.2 N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3SO.sub.2 N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3SO.sub.2 N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3SO.sub.2 N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3SO.sub.2 N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3SO.sub.2 N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3SO.sub.2 N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3SCH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3SCH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3SCH.sub.3 CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3SCH.sub.3 CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3SCH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3SCH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3SCH.sub.3 CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3SCH.sub.3 CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H CH 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2).sub.2 OCH.sub.3 H CH Cl OCH.sub.3CO.sub.2 CH.sub.2 CHCH.sub.2 (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3CO.sub.2 CH.sub.2 CHCH.sub.2 (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.2 CHCH.sub.2 (CH.sub.2).sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3CO.sub.2 CH.sub.2 CHCH.sub.2 (CH.sub.2).sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3OCH.sub.2 Cl (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.2 Cl (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3SCH.sub.2 Cl (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3SCH.sub.2 Cl (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3NH.sub.2 (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3NH.sub.2 (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3NHCH.sub.3 (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3NHCH.sub.3 (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3N(CH.sub.3).sub.2 (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 (CH.sub.2).sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 (CH.sub.2).sub.2 OCH.sub.3 H CH Cl OCH.sub.3N(CH.sub.3).sub.2 (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3N(CH.sub.3).sub.2 (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 (CH.sub.2).sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 (CH.sub.2).sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3N(CH.sub.3)CH.sub.2 CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3N(CH.sub.3)CH.sub.2 CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3C(O)N(CH.sub.3).sub.2 (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3C(O)N(CH.sub.3).sub.2 (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub. 3C(O)N(CH.sub.3).sub.2 (CH.sub.2).sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3C(O)N(CH.sub.3).sub.2 (CH.sub.2).sub.2 OCH.sub.3 H CH Cl OCH.sub.3C(O)N(CH.sub.3).sub.2 (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3C(O)N(CH.sub.3).sub.2 (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3C(O)N(CH.sub.3).sub.2 (CH.sub.2).sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3C(O)N(CH.sub.3).sub.2 (CH.sub.2).sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 OH H CH CH.sub.3 CH.sub.3H CH.sub.2 OH H CH CH.sub.3 OCH.sub.3H CH.sub.2 OH H CH OCH.sub.3 OCH.sub.3H CH.sub.2 OH H CH Cl OCH.sub.3H CH.sub.2 OH H N CH.sub.3 CH.sub.3H CH.sub.2 OH H N CH.sub.3 CH.sub.3H CH.sub.2 OH H N OCH.sub.3 OCH.sub.3H CH.sub.2 OH H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 OH CH.sub.3 N CH.sub.3 OCH.sub.3H CH(CH.sub.3)OH H CH CH.sub.3 CH.sub.3 183-185H CH(CH.sub.3)OH H CH CH.sub.3 OCH.sub.3 153-156H CH(CH.sub.3)OH H CH OCH.sub.3 OCH.sub.3 135-139H CH(CH.sub.3)OH H CH Cl OCH.sub.3 128-130H CH(CH.sub.3)OH H N OCH.sub.3 OCH.sub.3 142-145H CH(OH)CH.sub.2 CH.sub.3 H CH CH.sub.3 CH.sub.3 161-164H CH(OH)CH.sub.2 CH.sub.3 H CH OCH.sub.3 OCH.sub.3 133-135H CH(OH)CH.sub.2 CH.sub.3 H CH Cl OCH.sub.3 124-127H CH(OH)CH.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3 138-141H CH(OH)CH.sub.2 CH.sub.3 H N OCH.sub.3 OCH.sub.3 199-202H CH(OH)CH(CH.sub.3).sub.2 H CH CH.sub.3 CH.sub.3 179-181H CH(OH)CH(CH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3 140-142H CH(OH)CH(CH.sub.3).sub.2 H CH OCH.sub.3 OCH.sub.3 135-138H CH(OH)CH(CH.sub.3).sub.2 H CH Cl OCH.sub.3 144-146H CH(OH)CH(CH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3 129-131H CH(OH)CH(CH.sub.3).sub.2 H N OCH.sub.3 OCH.sub.3 148-150H (CH.sub.2).sub.3 OCH.sub.3 H CH CH.sub. 3 OCH.sub.3 127-129H (CH.sub.2).sub.3 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3 133-134H (CH.sub.2).sub.3 OCH.sub.3 H N CH.sub.3 OCH.sub.3 121-123H (CH.sub.2).sub.3 OCH.sub.3 H N OCH.sub.3 OCH.sub.3 174-181H (CH.sub.2).sub.3 OCH.sub.3 H CH Cl OCH.sub.3 113-115H (CH.sub.2).sub.2 OH H CH CH.sub.3 CH.sub.3H (CH.sub.2).sub.2 OH H CH OCH.sub.3 CH.sub.3H (CH.sub.2).sub.2 OH H CH OCH.sub.3 OCH.sub.3 115-119H (CH.sub.2).sub.2 OH H CH Cl OCH.sub.3H (CH.sub.2).sub.2 OH H N CH.sub.3 CH.sub.3H (CH.sub.2).sub.2 OH H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 OH H N OCH.sub.3 OCH.sub.3 105-112dH (CH.sub.2).sub.2 OH H N OCH.sub.2 CH.sub.3 NHCH.sub.3H (CH.sub.2).sub.2 OH CH.sub.3 N CH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.2 CH.sub.3 H CH CH.sub.3 CH.sub.3H CH.sub.2 OCH.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3 150-153H CH.sub.2 OCH.sub.2 CH.sub.3 H CH OCH.sub.3 OCH.sub.3 138-143H CH.sub.2 OCH.sub.2 CH.sub.3 H CH Cl OCH.sub.3H CH.sub.2 OCH.sub.2 CH.sub.3 H N CH.sub.3 CH.sub.3H CH.sub.2 OCH.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3 141-145H CH.sub.2 OCH.sub.2 CH.sub.3 H N OCH.sub.3 OCH.sub.3 156-160H CH.sub.2 OCH.sub.2 CH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 OCH.sub.2 CH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 OCH.sub.2 CH.sub.3 H CH CH.sub.3 CH.sub.3H (CH.sub.2).sub.2 OCH.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 OCH.sub.2 CH.sub.3 H CH OCH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 OCH.sub.2 CH.sub.3 H CH Cl OCH.sub.3H (CH.sub.2).sub.2 OCH.sub.2 CH.sub.3 H N CH.sub.3 CH.sub.3H (CH.sub.2).sub.2 OCH.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 OCH.sub. 2 CH.sub.3 H N OCH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 OCH.sub.2 CH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H (CH.sub.2).sub.2 OCH.sub.2 CH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.2 CHCH.sub.2 H CH CH.sub.3 CH.sub.3H CH.sub.2 OCH.sub.2 CHCH.sub.2 H CH CH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.2 CHCH.sub.2 H CH OCH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.2 CHCH.sub.2 H CH Cl OCH.sub.3H CH.sub.2 OCH.sub.2 CHCH.sub.2 H N CH.sub.3 CH.sub.3H CH.sub.2 OCH.sub.2 CHCH.sub.2 H N CH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.2 CHCH.sub.2 H N OCH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.2 CHCH.sub.2 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 OCH.sub.2 CHCH.sub.2 CH.sub.3 N CH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.2 CCH H CH CH.sub.3 CH.sub.3H CH.sub.2 OCH.sub.2 C CH H CH CH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.2 CCH H CH OCH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.2 CCH H CH Cl OCH.sub.3H CH.sub.2 OCH.sub.2 CCH H N CH.sub.3 CH.sub.3H CH.sub.2 OCH.sub.2 CCH H N CH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.2 CCH H N OCH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.2 CCH H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 OCH.sub.2 CCH CH.sub.3 N CH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.2 Cl H CH CH.sub.3 CH.sub.3H CH.sub.2 OCH.sub.2 Cl H CH CH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.2 Cl H CH OCH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.2 Cl H CH Cl OCH.sub.3H CH.sub.2 OCH.sub.2 Cl H N CH.sub.3 CH.sub.3H CH.sub.2 OCH.sub.2 Cl H N CH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.2 Cl H N OCH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.2 Cl H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 OCH.sub.2 Cl CH.sub.3 N CH.sub.3 OCH.sub.3H CH.sub.2 O(CH.sub.2).sub.2 Cl H CH CH.sub.3 CH.sub.3H CH.sub.2 O(CH.sub.2).sub.2 Cl H CH CH.sub.3 OCH.sub.3H CH.sub.2 O(CH.sub.2).sub.2 Cl H CH OCH.sub.3 OCH.sub.3H CH.sub.2 O(CH.sub.2).sub.2 Cl H CH Cl OCH.sub.3H CH.sub.2 O(CH.sub.2).sub.2 Cl H N CH.sub.3 CH.sub.3H CH.sub.2 O(CH.sub.2).sub.2 Cl H N CH.sub.3 OCH.sub.3H CH.sub.2 O(CH.sub.2).sub.2 Cl H N OCH.sub.3 OCH.sub.3H CH.sub.2 O(CH.sub.2).sub.2 Cl H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 O(CH.sub.2).sub.2 Cl CH.sub.3 N CH.sub.3 OCH.sub.3H CH.sub.2 OSO.sub.2 CH.sub.3 H CH CH.sub.3 CH.sub.3H CH.sub.2 OSO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 OSO.sub.2 CH.sub.3 H CH OCH.sub.3 OCH.sub.3H CH.sub.2 OSO.sub.2 CH.sub.3 H CH Cl OCH.sub.3H CH.sub.2 OSO.sub.2 CH.sub.3 H N CH.sub.3 CH.sub.3H CH.sub.2 OSO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 OSO.sub.2 CH.sub.3 H N OCH.sub.3 OCH.sub.3H CH.sub.2 OSO.sub.2 CH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 OSO.sub.2 CH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3H CH.sub.2 OC(O)CH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 OC(O)CH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 OC(O)CH.sub.3 H CH OCH.sub.3 OCH.sub.3H CH.sub.2 OC(O)CH.sub.3 H CH Cl OCH.sub.3H CH.sub.2 OC(O)CH.sub.3 H N CH.sub.3 CH.sub.3H CH.sub.2 OC(O)CH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 OC(O)CH.sub.3 H N OCH.sub. 3 OCH.sub.3H CH.sub.2 OC(O)CH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 OC(O)CH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3H CH.sub.2 OC(O)CH.sub.2 CH.sub.3 H CH CH.sub.3 CH.sub.3H CH.sub.2 OC(O)CH.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 OC(O)CH.sub.2 CH.sub.3 H CH OCH.sub.3 OCH.sub.3H CH.sub.2 OC(O)CH.sub.2 CH.sub.3 H CH Cl OCH.sub.3H CH.sub.2 OC(O)CH.sub.2 CH.sub.3 H N CH.sub.3 CH.sub.3H CH.sub.2 OC(O)CH.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 OC(O)CH.sub.2 CH.sub.3 H N OCH.sub.3 OCH.sub.3H CH.sub.2 OC(O)CH.sub.2 CH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 OC(O)CH.sub.2 CH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3H CH.sub.2 SCH.sub.3 H CH CH.sub.3 CH.sub.3 177-179.degree.H CH.sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3 130-133.degree.H CH.sub.2 SCH.sub.3 H CH OCH.sub.3 OCH.sub.3 145-147.degree.H CH.sub.2 SCH.sub.3 H CH Cl OCH.sub.3 135- 137.degree.H CH.sub.2 SCH.sub.3 H N CH.sub.3 CH.sub.3H CH.sub.2 SCH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 SCH.sub.3 H N OCH.sub.3 OCH.sub.3H CH.sub.2 SCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 SCH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3Cl CH.sub.2 OCH.sub.2 CH.sub.3 H CH CH.sub.3 CH.sub.3Cl CH.sub.2 OCH.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 OCH.sub.2 CH.sub.3 H CH OCH.sub.3 OCH.sub.3Cl CH.sub.2 OCH.sub.2 CH.sub.3 H CH Cl OCH.sub.3Cl CH.sub.2 OCH.sub.2 CH.sub.3 H N CH.sub.3 CH.sub.3Cl CH.sub.2 OCH.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3Cl CH.sub.2 OCH.sub.2 CH.sub.3 H N OCH.sub.3 OCH.sub.3Cl CH.sub.2 OCH.sub.2 CH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3Cl CH.sub.2 OCH.sub.2 CH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3SCH.sub.3 CH.sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3SCH.sub.3 CH.sub.2 SCH.sub.3 H N CH.sub. 3 OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 SCH.sub.3 H CH CH.sub.3 CH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 SCH.sub.3 H CH OCH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 SCH.sub.3 H CH Cl OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 SCH.sub.3 H N CH.sub.3 CH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 SCH.sub.3 H N CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 SCH.sub.3 H N OCH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 SCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 SCH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3CO.sub.2 N(CH.sub.3).sub.2 CH.sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3CO.sub.2 N(CH.sub.3).sub.2 CH.sub.2 SCH.sub.3 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 SCH.sub.3 H CH CH.sub.3 CH.sub.3H (CH.sub.2).sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3 119-125H (CH.sub.2).sub.2 SCH.sub.3 H CH OCH.sub.3 OCH.sub.3 103-107H (CH.sub.2).sub.2 SCH.sub.3 H CH Cl OCH.sub.3H (CH.sub.2).sub.2 SCH.sub.3 H N CH.sub.3 CH.sub.3H (CH.sub.2).sub.2 SCH.sub.3 H N CH.sub.3 OCH.sub.3 111dH (CH.sub.2).sub.2 SCH.sub.3 H N OCH.sub.3 OCH.sub.3 119-122H (CH.sub.2).sub.2 SCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H (CH.sub.2).sub.2 SCH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3Cl (CH.sub.2).sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3Cl (CH.sub.2).sub.2 SCH.sub.3 H N CH.sub.3 OCH.sub.3SCH.sub.3 (CH.sub.2).sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3SCH.sub.3 (CH.sub.2).sub.2 SCH.sub.3 H N CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 (CH.sub.2).sub.2 SCH.sub.3 H CH CH.sub.3 CH.sub.3CO.sub.2 CH.sub.3 (CH.sub.2).sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 (CH.sub.2).sub.2 SCH.sub.3 H CH OCH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 (CH.sub.2).sub.2 SCH.sub. 3 H CH Cl OCH.sub.3CO.sub.2 CH.sub.3 (CH.sub.2).sub.2 SCH.sub.3 H N CH.sub.3 CH.sub.3CO.sub.2 CH.sub.3 (CH.sub.2).sub.2 SCH.sub.3 H N CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 (CH.sub.2).sub.2 SCH.sub.3 H N OCH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 (CH.sub.2).sub.2 SCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3CO.sub.2 CH.sub.3 (CH.sub.2).sub.2 SCH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3CON(CH.sub.3).sub.2 (CH.sub.2).sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3CON(CH.sub.3).sub.2 (CH.sub.2).sub.2 SCH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 SH H CH CH.sub.3 CH.sub.3H CH.sub.2 SH H CH CH.sub.3 OCH.sub.3H CH.sub.2 SH H CH OCH.sub.3 OCH.sub.3H CH.sub.2 SH H CH Cl OCH.sub.3H CH.sub.2 SH H N CH.sub.3 CH.sub.3H CH.sub.2 SH H N CH.sub.3 OCH.sub.3H CH.sub.2 SH H N OCH.sub.3 OCH.sub.3H CH.sub.2 SH H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 SH CH.sub.3 N CH.sub.3 OCH.sub.3H CH.sub.2 SCH.sub.2 CH.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3 116-120H CH.sub.2 SCH.sub.2 CH.sub.2 CH.sub.3 H CH OCH.sub.3 OCH.sub.3 111-114H CH.sub.2 SCH.sub.2 CH.sub.2 CH.sub.3 H CH Cl OCH.sub.3 108-112H CH.sub.2 SCH.sub.2 CH.sub.2 CH.sub.3 H CH CH.sub.3 CH.sub.3 152-156H CH.sub.2 SCH.sub.2 CH.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3 122-125dH CH.sub.2 SCH.sub.2 CHCH.sub.2 H CH CH.sub.3 CH.sub.3H CH.sub.2 SCH.sub.2 CHCH.sub.2 H CH CH.sub.3 OCH.sub.3H CH.sub.2 SCH.sub.2 CHCH.sub.2 H CH OCH.sub.3 OCH.sub.3H CH.sub.2 SCH.sub.2 CHCH.sub.2 H CH Cl OCH.sub.3H CH.sub.2 SCH.sub.2 CHCH.sub.2 H N CH.sub.3 CH.sub.3H CH.sub.2 SCH.sub.2 CHCH.sub.2 H N CH.sub.3 OCH.sub.3H CH.sub.2 SCH.sub.2 CHCH.sub.2 H N OCH.sub.3 OCH.sub.3H CH.sub.2 SCH.sub.2 CH CH.sub.2 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 SCH.sub.2 CHCH.sub.2 CH.sub.3 N CH.sub.3 OCH.sub.3H CH.sub.2 SCH.sub.2 CCH H CH CH.sub.3 CH.sub.3H CH.sub.2 SCH.sub.2 CCH H CH CH.sub.3 OCH.sub.3H CH.sub.2 SCH.sub.2 CCH H CH OCH.sub.3 OCH.sub.3H CH.sub.2 SCH.sub.2 CCH H CH Cl OCH.sub.3H CH.sub.2 SCH.sub.2 CCH H N CH.sub.3 CH.sub.3H CH.sub.2 SCH.sub.2 CCH H N CH.sub.3 OCH.sub.3H CH.sub.2 SCH.sub.2 CCH H N OCH.sub.3 OCH.sub.3H CH.sub.2 SCH.sub.2 CCH H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 SCH.sub.2 CCH CH.sub.3 N CH.sub.3 OCH.sub.3H CH.sub.2 SCH.sub.2 CH.sub.3 H CH CH.sub.3 CH.sub.3 135-140H CH.sub.2 SCH.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3 117-120H CH.sub.2 SCH.sub.2 CH.sub.3 H CH OCH.sub.3 OCH.sub.3 121-125H CH.sub.2 SCH.sub.2 CH.sub.3 H CH Cl OCH.sub.3 105-110H CH.sub.2 SCH.sub.2 CH.sub.3 H N CH.sub.3 CH.sub.3H CH.sub.2 SCH.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3 225-235dH CH.sub.2 SCH.sub.2 CH.sub.3 H N OCH.sub.3 OCH.sub.3H CH.sub.2 SCH.sub.2 CH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 SCH.sub.2 CH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3H CH(CH.sub.3)SCH.sub.3 H CH CH.sub.3 CH.sub.3 170-173H CH(CH.sub.3)SCH.sub.3 H CH CH.sub.3 OCH.sub.3 146-148H CH(CH.sub.3)SCH.sub.3 H CH OCH.sub.3 OCH.sub.3 145-150H CH(CH.sub.3)SCH.sub.3 H CH Cl OCH.sub.3 155-158H CH(CH.sub.3)SCH.sub.3 H N CH.sub.3 OCH.sub.3 139-142H CH(CH.sub.3)SCH.sub.3 H N OCH.sub.3 OCH.sub.3 135-138H CH.sub.2 SCH.sub.2 Cl H CH CH.sub.3 OCH.sub.3H CH.sub.2 S(CH.sub.2).sub.2 Cl H CH CH.sub.3 OCH.sub.3H CH.sub.2 SCO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 SCO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 SCO.sub.2 CH.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 SCO.sub.2 CH.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 S(O)CH.sub.3 H CH CH.sub.3 CH.sub.3H CH.sub.2 S(O)CH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 S(O)CH.sub.3 H CH OCH.sub.3 OCH.sub.3H CH.sub.2 S(O)CH.sub.3 H CH Cl OCH.sub.3H CH.sub.2 S(O)CH.sub.3 H N CH.sub.3 CH.sub.3H CH.sub.2 S(O)CH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 S(O)CH.sub.3 H N OCH.sub.3 OCH.sub.3H CH.sub.2 S(O)CH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 S(O)CH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3H CH.sub.2 CH.sub.2 S(O)CH.sub.3 H CH CH.sub.3 CH.sub.3H CH.sub.2 CH.sub.2 S(O)CH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 CH.sub.2 S(O)CH.sub.3 H CH OCH.sub.3 OCH.sub.3H CH.sub.2 CH.sub.2 S(O)CH.sub.3 H CH Cl OCH.sub.3H CH.sub.2 CH.sub.2 S(O)CH.sub.3 H N CH.sub.3 CH.sub.3H CH.sub.2 CH.sub.2 S(O)CH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 CH.sub.2 S(O)CH.sub.3 H N OCH.sub.3 OCH.sub.3H CH.sub.2 CH.sub.2 S(O)CH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 CH.sub.2 S(O)CH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3Cl CH.sub.2 S(O)CH.sub.3 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 S(O)CH.sub.3 H N CH.sub.3 OCH.sub.3SCH.sub.3 CH.sub.2 S(O)CH.sub.3 H CH CH.sub.3 OCH.sub.3SCH.sub.3 CH.sub.2 S(O)CH.sub.3 H N CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 S(O)CH.sub.3 H CH CH.sub.3 CH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 S(O)CH.sub. 3 H CH CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 S(O)CH.sub.3 H CH OCH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 S(O)CH.sub.3 H CH Cl OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 S(O)CH.sub.3 H N CH.sub.3 CH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 S(O)CH.sub.3 H N CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 S(O)CH.sub.3 H N OCH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 S(O)CH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 S(O)CH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3CON(CH.sub.3).sub.2 CH.sub.2 S(O)CH.sub.3 H CH CH.sub.3 OCH.sub.3CON(CH.sub.3).sub.2 CH.sub.2 S(O)CH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 S(O)CH.sub.2 CH.sub.3 H CH CH.sub.3 CH.sub.3H CH.sub.2 S(O)CH.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 S(O)CH.sub.2 CH.sub.3 H CH OCH.sub.3 OCH.sub.3H CH.sub.2 S(O)CH.sub.2 CH.sub.3 H CH Cl OCH.sub.3H CH.sub.2 S(O)CH.sub.2 CH.sub.3 H N CH.sub.3 CH.sub.3H CH.sub.2 S(O)CH.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 S(O)CH.sub.2 CH.sub.3 H N OCH.sub.3 OCH.sub.3H CH.sub.2 S(O)CH.sub.2 CH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 S(O)CH.sub.2 CH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3H CH.sub.2 S(O)CH.sub.2 CHCH.sub.2 H CH CH.sub.3 CH.sub.3H CH.sub.2 S(O)CH.sub.2 CHCH.sub.2 H CH CH.sub.3 OCH.sub.3H CH.sub.2 S(O)CH.sub.2 CHCH.sub.2 H CH OCH.sub.3 OCH.sub.3H CH.sub.2 S(O)CH.sub.2 CHCH.sub.2 H CH Cl OCH.sub.3H CH.sub.2 S(O)CH.sub.2 CHCH.sub.2 H N CH.sub.3 CH.sub.3H CH.sub.2 S(O)CH.sub.2 CHCH.sub.2 H N CH.sub.3 OCH.sub.3H CH.sub.2 S(O)CH.sub.2 CHCH.sub.2 H N OCH.sub.3 OCH.sub.3H CH.sub.2 S(O)CH.sub.2 CHCH.sub.2 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 S(O)CH.sub.2 CHCH.sub.2 CH.sub.3 N CH.sub.3 OCH.sub.3H CH.sub.2 S(O)CH.sub.2 CCH H CH CH.sub.3 CH.sub.3H CH.sub.2 S(O)CH.sub.2 CCH H CH CH.sub.3 OCH.sub.3H CH.sub.2 S(O)CH.sub.2 CCH H CH OCH.sub.3 OCH.sub.3H CH.sub.2 S(O)CH.sub.2 CCH H CH Cl OCH.sub.3H CH.sub.2 S(O)CH.sub.2 CCH H N CH.sub.3 CH.sub.3H CH.sub.2 S(O)CH.sub.2 CCH H N CH.sub.3 OCH.sub.3H CH.sub.2 S(O)CH.sub.2 CCH H N OCH.sub.3 OCH.sub.3H CH.sub.2 S(O)CH.sub.2 CCH H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 S(O)CH.sub.2 CCH CH.sub.3 N CH.sub.3 OCH.sub.3H CH.sub.2 S(O)CH.sub.2 Cl H CH CH.sub.3 OCH.sub.3H CH.sub.2 S(O)CH.sub.2 Cl H N OCH.sub.3 OCH.sub.3H CH.sub.2 S(O)(CH.sub.2).sub.2 Cl H CH CH.sub.3 OCH.sub.3H CH.sub.2 S(O)(CH.sub.2).sub.2 Cl H N CH.sub.3 OCH.sub.3H CH.sub.2 SO.sub.2 CH.sub.3 H CH CH.sub.3 CH.sub.3 171-174.degree.H CH.sub.2 SO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3 121-125.degree.H CH.sub.2 SO.sub.2 CH.sub.3 H CH OCH.sub.3 OCH.sub.3 180-182.degree.H CH.sub.2 SO.sub.2 CH.sub.3 H CH Cl OCH.sub.3 175-179.degree.H CH.sub.2 SO.sub.2 CH.sub.3 H N CH.sub.3 CH.sub.3H CH.sub.2 SO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 SO.sub.2 CH.sub.3 H N OCH.sub.3 OCH.sub.3H CH.sub.2 SO.sub.2 CH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 SO.sub.2 CH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3H CH(CH.sub.3)SO.sub.2 CH.sub.3 H CH OCH.sub.3 OCH.sub.3 153-157H (CH.sub.2).sub.2 SO.sub.2 CH.sub.3 H CH CH.sub.3 CH.sub.3H (CH.sub.2).sub.2 SO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 SO.sub.2 CH.sub.3 H CH OCH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 SO.sub.2 CH.sub.3 H CH Cl OCH.sub.3H (CH.sub.2).sub.2 SO.sub.2 CH.sub.3 H N CH.sub.3 CH.sub.3H (CH.sub.2).sub.2 SO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 SO.sub.2 CH.sub.3 H N OCH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 SO.sub.2 CH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H (CH.sub.2).sub.2 SO.sub.2 CH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3Cl CH.sub.2 SO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 SO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3SCH.sub.3 CH.sub.2 SO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3SCH.sub.3 CH.sub.2 SO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 SO.sub.2 CH.sub.3 H CH CH.sub.3 CH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 SO.sub.2 CH.sub.3 H CH CH.sub. 3 OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 SO.sub.2 CH.sub.3 H CH OCH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 SO.sub.2 CH.sub.3 H CH Cl OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 SO.sub.2 CH.sub.3 H N CH.sub.3 CH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 SO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 SO.sub.2 CH.sub.3 H N OCH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 SO.sub.2 CH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 SO.sub.2 CH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3CON(CH.sub.3).sub.2 CH.sub.2 SO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3CON(CH.sub.3).sub.2 CH.sub.2 SO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.3 H CH CH.sub.3 CH.sub.3H CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.3 H CH OCH.sub.3 OCH.sub.3H CH.sub.2 SO.sub.2 CH.sub. 2 CH.sub.3 H CH Cl OCH.sub.3H CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.3 H N CH.sub.3 CH.sub.3H CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.3 H N OCH.sub.3 OCH.sub.3H CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3H CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3 174-177H CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H CH OCH.sub.3 OCH.sub.3 190-193H CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3 150-153H CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H N OCH.sub.3 OCH.sub.3 146-148dH CH.sub.2 SO.sub.2 CH.sub.2 CHCH.sub.2 H CH CH.sub.3 CH.sub.3H CH.sub.2 SO.sub.2 CH.sub.2 CHCH.sub.2 H CH CH.sub.3 OCH.sub.3H CH.sub.2 SO.sub.2 CH.sub. 2 CHCH.sub.2 H CH OCH.sub.3 OCH.sub.3H CH.sub.2 SO.sub.2 CH.sub.2 CHCH.sub.2 H CH Cl OCH.sub.3H CH.sub.2 SO.sub.2 CH.sub.2 CHCH.sub.2 H N CH.sub.3 CH.sub.3H CH.sub.2 SO.sub.2 CH.sub.2 CHCH.sub.2 H N CH.sub.3 OCH.sub.3H CH.sub.2 SO.sub.2 CH.sub.2 CHCH.sub.2 H N OCH.sub.3 OCH.sub.3H CH.sub.2 SO.sub.2 CH.sub.2 CHCH.sub.2 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 SO.sub.2 CH.sub.2 CHCH.sub.2 CH.sub.3 N CH.sub.3 OCH.sub.3H CH.sub.2 SO.sub.2 CH.sub.2 CCH H CH CH.sub.3 CH.sub.3H CH.sub.2 SO.sub.2 CH.sub.2 CCH H CH CH.sub.3 OCH.sub.3H CH.sub.2 SO.sub.2 CH.sub.2 CCH H CH OCH.sub.3 OCH.sub.3H CH.sub.2 SO.sub.2 CH.sub.2 CCH H CH Cl OCH.sub.3H CH.sub.2 SO.sub.2 CH.sub.2 CCH H N CH.sub.3 CH.sub.3H CH.sub.2 SO.sub.2 CH.sub.2 CCH H N CH.sub.3 OCH.sub.3H CH.sub.2 SO.sub.2 CH.sub.2 CCH H N OCH.sub.3 OCH.sub.3H CH.sub.2 SO.sub.2 CH.sub.2 CCH H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 SO.sub.2 CH.sub.2 CCH CH.sub.3 N CH.sub.3 OCH.sub.3H CH.sub.2 SO.sub.2 CH.sub.2 Cl H CH CH.sub.3 OCH.sub.3H CH.sub.2 SO.sub.2 CH.sub.2 Cl H N CH.sub.3 OCH.sub.3H CH.sub.2 SO.sub.2 (CH.sub.2).sub.2 Cl H CH CH.sub.3 OCH.sub.3H CH.sub.2 SO.sub.2 (CH.sub.2).sub.2 Cl H N CH.sub.3 OCH.sub.3H CH.sub.2 CO.sub.2 CH.sub.3 H CH CH.sub.3 CH.sub.3H CH.sub.2 CO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3 154-156.6H CH.sub.2 CO.sub.2 CH.sub.3 H CH OCH.sub.3 OCH.sub.3 167-169H CH.sub.2 CO.sub.2 CH.sub.3 H CH Cl OCH.sub.3 159-161.5H CH.sub.2 CO.sub.2 CH.sub.3 H N CH.sub.3 CH.sub.3H CH.sub.2 CO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3 143-147H CH.sub.2 CO.sub.2 CH.sub.3 H N OCH.sub.3 OCH.sub.3 134-139H CH.sub.2 CO.sub.2 CH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 CO.sub.2 CH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CO.sub.2 CH.sub.3 H CH CH.sub.3 CH.sub.3H (CH.sub.2).sub.2 CO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CO.sub.2 CH.sub.3 H CH OCH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CO.sub.2 CH.sub.3 H CH Cl OCH.sub.3H (CH.sub.2).sub.2 CO.sub.2 CH.sub.3 H N CH.sub.3 CH.sub.3H (CH.sub.2).sub.2 CO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CO.sub.2 CH.sub.3 H N OCH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CO.sub.2 CH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H (CH.sub.2).sub.2 CO.sub.2 CH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3Cl CH.sub.2 CO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 CO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3SCH.sub.3 CH.sub.2 CO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3SCH.sub.3 CH.sub.2 CO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 CO.sub.2 CH.sub.3 H CH CH.sub.3 CH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 CO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 CO.sub.2 CH.sub.3 H CH OCH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 CO.sub.2 CH.sub.3 H CH Cl OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 CO.sub.2 CH.sub.3 H N CH.sub.3 CH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 CO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub. 3CO.sub.2 CH.sub.3 CH.sub.2 CO.sub.2 CH.sub.3 H N OCH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 CO.sub.2 CH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CO.sub.2 CH.sub.3 CH.sub.2 CO.sub.2 CH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3H CON(CH.sub.3).sub.2 CH.sub.2 CO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3H CON(CH.sub.3).sub.2 CH.sub.2 CO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3 H CH CH.sub.3 CH.sub.3H CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3 H CH OCH.sub.3 OCH.sub.3H CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3 H CH Cl OCH.sub.3H CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3 H N CH.sub.3 CH.sub.3H CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3 H N OCH.sub.3 OCH.sub.3H CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3 H N 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CH.sub.2 CO.sub.2 CH.sub.2 CCH H N OCH.sub.3 OCH.sub.3H CH.sub.2 CO.sub.2 CH.sub.2 CCH H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 CO.sub.2 CH.sub.2 CCH CH.sub.3 N CH.sub.3 OCH.sub.3H CH.sub.2 CO.sub.2 (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3H CH.sub.2 CO.sub.2 (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 CO.sub.2 (CH.sub.2).sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3H CH.sub.2 CO.sub.2 (CH.sub.2).sub.2 OCH.sub.3 H CH Cl OCH.sub.3H CH.sub.2 CO.sub.2 (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3H CH.sub.2 CO.sub.2 (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 CO.sub.2 (CH.sub.2).sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3H CH.sub.2 CO.sub.2 (CH.sub.2).sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 CO.sub.2 (CH.sub.2).sub.2 OCH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3H CH.sub.2 CO.sub.2 (CH.sub.2).sub.2 Cl H CH CH.sub.3 OCH.sub.3H CH.sub.2 CO.sub.2 (CH.sub.2).sub.2 Cl H N CH.sub.3 OCH.sub.3H CH.sub.2 C(O)NHCH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 C(O)NHCH.sub.3 H N CH.sub.3 OCH.sub.3H (CH.sub.2 ).sub.2 C(O)NHCH.sub.3 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 C(O)NHCH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 C(O)N(CH.sub.3).sub.2 H CH CH.sub.3 CH.sub.3H CH.sub.2 C(O)N(CH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H CH.sub.2 C(O)N(CH.sub.3).sub.2 H CH OCH.sub.3 OCH.sub.3 172-173H CH.sub.2 C(O)N(CH.sub.3).sub.2 H CH Cl OCH.sub.3H CH.sub.2 C(O)N(CH.sub.3).sub.2 H N CH.sub.3 CH.sub.3H CH.sub.2 C(O)N(CH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3H CH.sub.2 C(O)N(CH.sub.3).sub.2 H N OCH.sub.3 OCH.sub.3 99-100H CH.sub.2 C(O)N(CH.sub.3).sub.2 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 C(O)N(CH.sub.3).sub.2 CH.sub.3 N CH.sub.3 OCH.sub.3H CH.sub.2 C(O)N(CH.sub.3).sub.2 H CH CH.sub.3 CH.sub.3H CH.sub.2 C(O)N(CH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H CH.sub.2 C(O)N(CH.sub.3).sub.2 H CH OCH.sub.3 OCH.sub.3H CH.sub.2 C(O)N(CH.sub.3).sub.2 H CH Cl OCH.sub.3H CH.sub.2 C(O)N(CH.sub. 3).sub.2 H N CH.sub.3 CH.sub.3H CH.sub.2 C(O)N(CH.sub.3).sub.2 H N 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OCH.sub.3 OCH.sub.3H CH.sub.2 CHNOCH.sub.3 H CH Cl OCH.sub.3H CH.sub.2 CHNOCH.sub.3 H N CH.sub.3 CH.sub.3H CH.sub.2 CHNOCH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 CHNOCH.sub.3 H N OCH.sub.3 OCH.sub.3H CH.sub.2 CHNOCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 CHNOCH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CHNOCH.sub.3 H CH CH.sub.3 CH.sub.3H (CH.sub.2).sub.2 CHNOCH.sub.3 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CHNOCH.sub.3 H CH OCH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CHNOCH.sub.3 H CH Cl OCH.sub.3H (CH.sub.2).sub.2 CHNOCH.sub.3 H N CH.sub.3 CH.sub.3H (CH.sub.2).sub.2 CHNOCH.sub.3 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CHNOCH.sub.3 H N OCH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CHNOCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H (CH.sub.2).sub.2 CHNOCH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3H CH.sub.2 C(CH.sub.3)NOCH.sub.3 H CH CH.sub.3 CH.sub.3H CH.sub.2 C(CH.sub.3)NOCH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 C(CH.sub.3)NOCH.sub.3 H CH OCH.sub.3 OCH.sub.3H CH.sub.2 C(CH.sub.3)NOCH.sub.3 H CH Cl OCH.sub.3H CH.sub.2 C(CH.sub.3)NOCH.sub.3 H N CH.sub.3 CH.sub.3H CH.sub.2 C(CH.sub.3)NOCH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 C(CH.sub.3)NOCH.sub.3 H N OCH.sub.3 OCH.sub.3H CH.sub.2 C(CH.sub.3)NOCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 C(CH.sub.3)NOCH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 C(CH.sub.3)NOCH.sub.3 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 C(CH.sub.3)NOCH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 CHNOCH.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 CHNOCH.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 C(CH.sub.3)NOCH.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 C(CH.sub.3)NOCH.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3 ##STR40## H CH CH.sub.3 CH.sub.3H ##STR41## H CH CH.sub.3 OCH.sub.3H ##STR42## H CH OCH.sub.3 OCH.sub.3H ##STR43## H CH Cl OCH.sub.3H ##STR44## H N CH.sub.3 CH.sub.3H ##STR45## H N CH.sub.3 OCH.sub.3H ##STR46## H N OCH.sub.3 OCH.sub.3H ##STR47## H N OCH.sub.2 CH.sub.3 NHCH.sub.3H ##STR48## CH.sub.3 N CH.sub.3 OCH.sub.3H ##STR49## H CH CH.sub.3 OCH.sub.3H ##STR50## H N CH.sub.3 OCH.sub.3H ##STR51## H CH CH.sub.3 OCH.sub.3H ##STR52## H N CH.sub.3 OCH.sub.3H ##STR53## H CH CH.sub.3 OCH.sub.3H ##STR54## H N CH.sub.3 OCH.sub.3H ##STR55## H CH CH.sub.3 CH.sub.3H ##STR56## H CH CH.sub.3 OCH.sub.3H ##STR57## H CH OCH.sub.3 OCH.sub.3H ##STR58## H CH Cl OCH.sub.3H ##STR59## H N CH.sub.3 CH.sub.3H ##STR60## H N CH.sub.3 OCH.sub.3H ##STR61## H N OCH.sub.3 OCH.sub.3H ##STR62## H N OCH.sub.2 CH.sub.3 NHCH.sub.3H ##STR63## CH.sub.3 N CH.sub.3 OCH.sub.3H ##STR64## H CH CH.sub.3 OCH.sub.3H ##STR65## H N CH.sub.3 OCH.sub.3H CH.sub.2 CH(OCH.sub.3).sub.2 H CH CH.sub.3 CH.sub.3H CH.sub.2 CH(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H CH.sub.2 CH(OCH.sub.3).sub.2 H CH OCH.sub.3 OCH.sub.3H CH.sub.2 CH(OCH.sub.3).sub.2 H CH Cl OCH.sub.3H CH.sub.2 CH(OCH.sub.3).sub.2 H N CH.sub.3 CH.sub.3H CH.sub.2 CH(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3H CH.sub.2 CH(OCH.sub.3).sub.2 H N OCH.sub.3 OCH.sub.3H CH.sub.2 CH(OCH.sub.3).sub.2 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 CH(OCH.sub.3).sub.2 CH.sub.3 N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CH(OCH.sub.3).sub.2 H CH CH.sub.3 CH.sub.3H (CH.sub.2).sub.2 CH(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H (CH.sub. 2).sub.2 CH(OCH.sub.3).sub.2 H CH OCH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CH(OCH.sub.3).sub.2 H CH Cl OCH.sub.3H (CH.sub.2).sub.2 CH(OCH.sub.3).sub.2 H N CH.sub.3 CH.sub.3H (CH.sub.2).sub.2 CH(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CH(OCH.sub.3).sub.2 H N OCH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CH(OCH.sub.3).sub.2 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H (CH.sub.2).sub.2 CH(OCH.sub.3).sub.2 CH.sub.3 N CH.sub.3 OCH.sub.3Cl CH.sub.2 CH(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 CH(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3SCH.sub.3 CH.sub.2 CH(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3SCH.sub.3 CH.sub.2 CH(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 CH(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 CH(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3C(O)N(CH.sub.3).sub.2 CH.sub.2 CH(OCH.sub.3).sub. 2 H CH CH.sub.3 OCH.sub.3C(O)N(CH.sub.3).sub.2 CH.sub.2 CH(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3H CH.sub.2 CH(SCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H CH.sub.2 CH(SCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3H CH.sub.2 C(CH.sub.3)(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H CH.sub.2 C(CH.sub.3)(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3H CH.sub.2 C(CH.sub.3)(SCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H CH.sub.2 C(CH.sub.3)(SCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3H CH.sub.2 CH(OCH.sub.2 CH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H CH.sub.2 CH(OCH.sub.2 CH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3H CH.sub.2 CH(OCH.sub.2 CH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H CH.sub.2 CH(OCH.sub.2 CH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CH(OCH.sub.2 CH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CH(OCH.sub.2 CH.sub.3).sub.2 H N CH.sub. 3 OCH.sub.3H CH.sub.2 P(O)(OCH.sub.2 CH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3 116-118H CH.sub.2 P(O)(OCH.sub.2 CH.sub.3).sub.2 H CH OCH.sub.3 OCH.sub.3 139-140H CH.sub.2 P(O)(OCH.sub.2 CH.sub.3).sub.2 H N OCH.sub.3 OCH.sub.3 115-116__________________________________________________________________________
TABLE 2__________________________________________________________________________ ##STR66##R.sub.1 Q R Z X Y m.p. (.degree.C.)__________________________________________________________________________CH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3CH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3CH.sub.3 CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3CH.sub.3 CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3CH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3CH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3CH.sub.3 CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3CH.sub.3 CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3CH.sub.3 CH.sub.2 OCH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub. 3F CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3F CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3F CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3F CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3F CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3F CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3F CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3F CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3F CH.sub.2 OCH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3Cl CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3Cl CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3 206-209Cl CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3 187-190Cl CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3Cl CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3Cl CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3Cl CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3 175-178Cl CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3Cl CH.sub.2 OCH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3F (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3F (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3Cl (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3Cl (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3Cl CH.sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 SCH.sub.3 H N CH.sub.3 OCH.sub.3Cl (CH.sub.2).sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3Cl (CH.sub.2).sub.2 SCH.sub.3 H N CH.sub.3 OCH.sub.3Cl CH.sub.2 S(O)CH.sub.3 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 S(O)CH.sub.3 H N CH.sub.3 OCH.sub.3Cl CH.sub.2 SO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 SO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3Cl CH.sub.2 CO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 CO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3Cl CH.sub.2 C(O)N(CH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 C(O)N(CH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3Cl CH.sub.2 CN H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 CN H N CH.sub.3 OCH.sub.3Cl CH.sub.2 CHNOCH.sub.3 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 CHNOCH.sub.3 H N CH.sub.3 OCH.sub.3Cl CH.sub.2 C(CH.sub.3)NOCH.sub.3 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 C(CH.sub.3)NOCH.sub.3 H N CH.sub.3 OCH.sub.3Cl ##STR67## H CH CH.sub.3 OCH.sub.3Cl ##STR68## H N CH.sub.3 OCH.sub.3Cl ##STR69## H CH CH.sub.3 OCH.sub.3Cl ##STR70## H N CH.sub.3 OCH.sub.3Cl CH.sub.2 CH(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 CH(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3__________________________________________________________________________
TABLE 3__________________________________________________________________________ ##STR71##R.sub.1 Q R Z X Y__________________________________________________________________________OCH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub. 3 H CH CH.sub.3 CH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3S(O)CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3S(O)CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 SCH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 (CH.sub.2).sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 (CH.sub.2).sub.2 SCH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 S(O)CH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 S(O)CH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub. 2 SO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 SO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 C(O)N(CH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 C(O)N(CH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CN H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CN H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CHNOCH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CHNOCH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 C(CH.sub.3)NOCH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 C(CH.sub.3)NOCH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 ##STR72## H CH CH.sub.3 OCH.sub.3OCH.sub.3 ##STR73## H N CH.sub.3 OCH.sub.3OCH.sub.3 ##STR74## H CH CH.sub.3 OCH.sub.3OCH.sub.3 ##STR75## H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CH(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CH(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CH(SCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CH(SCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 C(CH.sub.3)(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 C(CH.sub.3)(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3OCH.sub.3 (CH.sub.2).sub.2 CH(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3OCH.sub.3 (CH.sub.2).sub.2 CH(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3__________________________________________________________________________
TABLE 4__________________________________________________________________________ ##STR76##R.sub.1 Q R Z X Y__________________________________________________________________________H CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3H CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3H CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3H CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3H (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 OCH.sub.3 H CH Cl OCH.sub.3H (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3H (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 SCH.sub.3 H CH CH.sub.3 CH.sub.3H CH.sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 SCH.sub.3 H CH OCH.sub.3 OCH.sub.3H CH.sub.2 SCH.sub.3 H CH Cl OCH.sub.3H CH.sub.2 SCH.sub.3 H N CH.sub.3 CH.sub.3H CH.sub.2 SCH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 SCH.sub.3 H N OCH.sub.3 OCH.sub.3H CH.sub.2 SCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H (CH.sub.2).sub.2 SCH.sub.3 H CH CH.sub.3 CH.sub.3H (CH.sub.2).sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 SCH.sub. 3 H CH OCH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 SCH.sub.3 H CH Cl OCH.sub.3H (CH.sub.2).sub.2 SCH.sub.3 H N CH.sub.3 CH.sub.3H (CH.sub.2).sub.2 SCH.sub.3 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 SCH.sub.3 H N OCH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 SCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 S(O)CH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 S(O)CH.sub.3 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 S(O)CH.sub.3 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 S(O)CH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 SO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 SO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 SO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 SO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 CO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 CO.sub.2 CH.sub.3 H N CH.sub. 3 OCH.sub.3H (CH.sub.2).sub.2 CO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 C(O)N(CH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H CH.sub.2 C(O)N(CH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 C(O)N(CH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 C(O)N(CH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3H CH.sub.2 CN H CH CH.sub.3 OCH.sub.3H CH.sub.2 CN H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CN H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CN H N CH.sub.3 OCH.sub.3H CH.sub.2 CHNOCH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 CHNOCH.sub.3 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CHNOCH.sub.3 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CHNOCH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 C(CH.sub.3)NOCH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 C(CH.sub.3)NOCH.sub.3 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 C(CH.sub.3)NOCH.sub.3 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 C(CH.sub.3)NOCH.sub.3 H N CH.sub.3 OCH.sub.3 ##STR77## H CH CH.sub.3 OCH.sub.3H ##STR78## H N CH.sub.3 OCH.sub.3H ##STR79## H CH CH.sub.3 OCH.sub.3H ##STR80## H N CH.sub.3 OCH.sub.3H CH.sub.2 CH(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H CH.sub.2 CH(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CH(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CH(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3H CH.sub.2 CH(SCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H CH.sub.2 CH(SCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CH(SCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CH(SCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3H CH.sub.2 C(CH.sub.3)(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H CH.sub.2 C(CH.sub.3)(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 C(CH.sub.3)(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 C(CH.sub.3)(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3H CH.sub.2 C(CH.sub.3)(SCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H CH.sub.2 C(CH.sub.3)(SCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 C(CH.sub.3)(SCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 C(CH.sub.3)(SCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3F CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3F CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3CH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3CH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3__________________________________________________________________________
TABLE 5__________________________________________________________________________ ##STR81##R.sub.1 Q R Z X Y__________________________________________________________________________OCH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3OCH.sub.3 CO.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub. 3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3S(O)CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3S(O)CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 SCH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 (CH.sub.2).sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 (CH.sub.2).sub.2 SCH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 S(O)CH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 S(O)CH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 SO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 SO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 C(O)N(CH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 C(O)N(CH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CN H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CN H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CHNOCH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CHNOCH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 C(CH.sub.3)NOCH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 C(CH.sub.3)NOCH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 ##STR82## H CH CH.sub.3 OCH.sub.3OCH.sub.3 ##STR83## H N CH.sub.3 OCH.sub.3OCH.sub.3 ##STR84## H CH CH.sub.3 OCH.sub.3OCH.sub.3 ##STR85## H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CH(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CH(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CH(SCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CH(SCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 C(CH.sub.3)(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 C(CH.sub.3)(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3OCH.sub.3 (CH.sub.2).sub.2 CH(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3OCH.sub.3 (CH.sub.2).sub.2 CH(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3__________________________________________________________________________
TABLE 6______________________________________ ##STR86##R.sub.1 Q R Z X Y______________________________________CH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3CH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3CH.sub.3 CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3CH.sub.3 CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3CH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3CH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3CH.sub.3 CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3CH.sub.3 CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3CH.sub.3 CH.sub.2 OCH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3F CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3F CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3F CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3F CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3F CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3F CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3F CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3F CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3F CH.sub.2 OCH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3Cl CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3Cl CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3Cl CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3Cl CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3Cl CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3Cl CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3Cl CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3Cl CH.sub.2 OCH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3CH.sub.3 (CH.sub.2).sub. 2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3F (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3F (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3Cl (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3Cl (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3Cl CH.sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 SCH.sub.3 H N CH.sub.3 OCH.sub.3Cl (CH.sub.2).sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3Cl (CH.sub.2).sub.2 SCH.sub.3 H N CH.sub.3 OCH.sub.3Cl CH.sub.2 S(O)CH.sub.3 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 S(O)CH.sub.3 H N CH.sub.3 OCH.sub.3Cl CH.sub.2 SO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 SO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3Cl CH.sub.2 CO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 CO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3Cl CH.sub.2 C(O)N(CH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 C(O)N(CH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3Cl CH.sub.2 CN H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 CN H N CH.sub.3 OCH.sub.3Cl CH.sub.2 CHNOCH.sub.3 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 CHNOCH.sub.3 H N CH.sub.3 OCH.sub.3Cl CH.sub.2 C(CH.sub.3)NOCH.sub.3 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 C(CH.sub.3)NOCH.sub.3 H N CH.sub.3 OCH.sub.3Cl ##STR87## H CH CH.sub.3 OCH.sub.3Cl ##STR88## H N CH.sub.3 OCH.sub.3Cl ##STR89## H CH CH.sub.3 OCH.sub.3Cl ##STR90## H N CH.sub.3 OCH.sub.3Cl CH.sub.2 CH(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 CH(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3Cl CH.sub.2 CH(SCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 CH(SCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3Cl CH.sub.2 C(CH.sub.3)(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 C(CH.sub.3)(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3Cl (CH.sub.2).sub.2 CH(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3Cl (CH.sub.2).sub.2 CH(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3______________________________________
TABLE 7__________________________________________________________________________ ##STR91##R.sub.1 Q R Z X Y__________________________________________________________________________H CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3H CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3H CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3H CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3H (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 OCH.sub.3 H CH Cl OCH.sub.3H (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3H (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 SCH.sub.3 H CH CH.sub.3 CH.sub.3H CH.sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 SCH.sub.3 H CH OCH.sub.3 OCH.sub.3H CH.sub.2 SCH.sub.3 H CH Cl OCH.sub.3H CH.sub.2 SCH.sub.3 H N CH.sub.3 CH.sub.3H CH.sub.2 SCH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 SCH.sub.3 H N OCH.sub.3 OCH.sub.3H CH.sub.2 SCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 SCH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 SCH.sub.3 H CH CH.sub.3 CH.sub.3H (CH.sub.2).sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 SCH.sub.3 H CH OCH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 SCH.sub.3 H CH Cl OCH.sub.3H (CH.sub.2).sub.2 SCH.sub.3 H N CH.sub.3 CH.sub.3H (CH.sub.2).sub.2 SCH.sub.3 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 SCH.sub.3 H N OCH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 SCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H (CH.sub.2).sub.2 SCH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3H CH.sub.2 SCH.sub.2 CHCH.sub.2 H CH CH.sub.3 OCH.sub.3H CH.sub.2 SCH.sub.2 CHCH.sub.2 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 SCH.sub.2 CHCH.sub.2 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 SCH.sub.2 CHCH.sub.2 H N CH.sub.3 OCH.sub.3H CH.sub.2 S(O)CH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 S(O)CH.sub.3 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 S(O)CH.sub.3 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 S(O)CH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 SO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 SO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 SO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 SO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 CO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 CO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 C(O)N(CH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H CH.sub.2 C(O)N(CH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 C(O)N(CH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 C(O)N(CH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3H CH.sub.2 CN H CH CH.sub.3 OCH.sub.3H CH.sub.2 CN H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CN H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CN H N CH.sub.3 OCH.sub.3H CH.sub.2 CHNOCH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 CHNOCH.sub.3 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CHNOCH.sub.3 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CHNOCH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 C(CH.sub.3)NOCH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 C(CH.sub.3)NOCH.sub.3 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 C(CH.sub.3)NOCH.sub.3 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 C(CH.sub.3)NOCH.sub.3 H N CH.sub.3 OCH.sub.3 ##STR92## H CH CH.sub.3 OCH.sub.3H ##STR93## H N CH.sub.3 OCH.sub.3H ##STR94## H CH CH.sub.3 OCH.sub.3H ##STR95## H N CH.sub.3 OCH.sub.3H ##STR96## H CH CH.sub.3 OCH.sub.3H ##STR97## H N CH.sub.3 OCH.sub.3H ##STR98## H CH CH.sub.3 OCH.sub.3H ##STR99## H N CH.sub.3 OCH.sub.3H CH.sub.2 CH(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H CH.sub.2 CH(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CH(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CH(OCH.sub.3).sub.2 H N CH.sub. 3 OCH.sub.3H CH.sub.2 CH(SCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H CH.sub.2 CH(SCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3H CH.sub.2 C(CH).sub.3)(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H CH.sub.2 C(CH).sub.3)(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 C(CH.sub.3)(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 C(CH.sub.3)(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 SCH.sub.3 H N CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 (CH.sub.2).sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3CO.sub.2 CH.sub. 3 (CH.sub.2).sub.2 SCH.sub.3 H N CH.sub.3 OCH.sub.3CH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3CH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3__________________________________________________________________________
TABLE 8__________________________________________________________________________ ##STR100##R.sub.1 O R Z X Y__________________________________________________________________________OCH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub. 3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3OCH.sub.3 (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3S(O)CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3S(O)CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 SCH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 (CH.sub.2).sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 (CH.sub.2).sub.2 SCH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 S(O)CH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 S(O)CH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 SO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 SO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 C(O)N(CH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 C(O)N(CH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CN H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CN H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CHNOCH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CHNOCH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 C(CH.sub.3)NOCH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 C(CH.sub.3)NOCH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 ##STR101## H CH CH.sub.3 OCH.sub.3OCH.sub.3 ##STR102## H N CH.sub.3 OCH.sub.3OCH.sub.3 ##STR103## H CH CH.sub.3 OCH.sub.3OCH.sub.3 ##STR104## H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CH(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CH(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CH(SCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CH(SCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 C(CH.sub.3)(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 C(CH.sub.3)(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3OCH.sub.3 (CH.sub.2).sub.2 CH(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3OCH.sub.3 (CH.sub.2).sub.2 CH(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3__________________________________________________________________________
TABLE 9______________________________________ ##STR105##R.sub.1 Q R Z X Y______________________________________CH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3CH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3CH.sub.3 CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3CH.sub.3 CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3CH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3CH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3CH.sub.3 CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3CH.sub.3 CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3CH.sub.3 CH.sub.2 OCH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3F CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3F CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3F CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3F CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3F CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3F CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3F CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3F CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3F CH.sub.2 OCH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3Cl CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3Cl CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3Cl CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3Cl CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3Cl CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3Cl CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3Cl CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3Cl CH.sub.2 OCH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3CH.sub.3 (CH.sub. 2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3F (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3F (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3Cl (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3Cl (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3Cl CH.sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 SCH.sub.3 H N CH.sub.3 OCH.sub.3Cl (CH.sub.2).sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3Cl (CH.sub.2).sub.2 SCH.sub.3 H N CH.sub.3 OCH.sub.3Cl CH.sub.2 S(O)CH.sub.3 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 S(O)CH.sub.3 H N CH.sub.3 OCH.sub.3Cl CH.sub.2 SO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 SO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3Cl CH.sub.2 CO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 CO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3Cl CH.sub.2 C(O)N(CH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 C(O)N(CH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3Cl CH.sub.2 CN H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 CN H N CH.sub.3 OCH.sub.3Cl CH.sub.2 CHNOCH.sub.3 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 CHNOCH.sub.3 H N CH.sub.3 OCH.sub.3Cl CH.sub.2 C(CH.sub.3)NOCH.sub.3 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 C(CH.sub.3)NOCH.sub.3 H N CH.sub.3 OCH.sub.3Cl ##STR106## H CH CH.sub.3 OCH.sub.3Cl ##STR107## H N CH.sub.3 OCH.sub.3Cl ##STR108## H CH CH.sub.3 OCH.sub.3Cl ##STR109## H N CH.sub.3 OCH.sub. 3Cl CH.sub.2 CH(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 CH(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3Cl CH.sub.2 CH(SCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 CH(SCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3Cl CH.sub.2 C(CH.sub.3)(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 C(CH.sub.3)(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3Cl (CH.sub.2).sub.2 CH(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3Cl (CH.sub.2).sub.2 CH(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3______________________________________
TABLE 10__________________________________________________________________________ ##STR110##R.sub.1 Q R Z X Y__________________________________________________________________________H CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3H CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3H CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3H CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3H (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub. 3H (CH.sub.2).sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 OCH.sub.3 H CH Cl OCH.sub.3H (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3H (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 SCH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 SCH.sub.2 CHCH.sub.2 H CH CH.sub.3 OCH.sub.3H CH.sub.2 SCH.sub.2 CHCH.sub.2 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 SCH.sub.2 CHCH.sub.2 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 SCH.sub.2 CHCH.sub.2 H N CH.sub.3 OCH.sub.3H CH.sub.2 S(O)CH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 S(O)CH.sub.3 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 S(O)CH.sub.3 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 S(O)CH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 SO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 SO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 SO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 SO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 CO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 CO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 C(O)N(CH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H CH.sub.2 C(O)N(CH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 C(O)N(CH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 C(O)N(CH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3H CH.sub.2 CN H CH CH.sub.3 OCH.sub.3H CH.sub.2 CN H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CN H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CN H N CH.sub.3 OCH.sub.3H CH.sub.2 CHNOCH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 CHNOCH.sub.3 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CHNOCH.sub.3 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CHNOCH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 C(CH.sub.3)NOCH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 C(CH.sub.3)NOCH.sub.3 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 C(CH.sub.3)NOCH.sub.3 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 C(CH.sub.3)NOCH.sub.3 H N CH.sub.3 OCH.sub.3 ##STR111## H CH CH.sub.3 OCH.sub.3H ##STR112## H N CH.sub.3 OCH.sub.3H ##STR113## H CH CH.sub.3 OCH.sub.3H ##STR114## H N CH.sub.3 OCH.sub.3H ##STR115## H CH CH.sub.3 OCH.sub.3H ##STR116## H N CH.sub.3 OCH.sub.3H ##STR117## H CH CH.sub.3 OCH.sub.3H ##STR118## H N CH.sub.3 OCH.sub.3H CH.sub.2 CH(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H CH.sub.2 CH(OCH.sub.3).sub.2 H N CH.sub. 3 OCH.sub.3H (CH.sub.2).sub.2 CH(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CH(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3H CH.sub.2 CH(SCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H CH.sub.2 CH(SCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3H CH.sub.2 C(CH.sub.3)(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H CH.sub.2 C(CH.sub.3)(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 C(CH.sub.3)(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 C(CH.sub.3)(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3CO.sub.2 CH.sub. 3 CH.sub.2 SCH.sub.3 H N CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 (CH.sub.2).sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 (CH.sub.2).sub.2 SCH.sub.3 H N CH.sub.3 OCH.sub.3Cl CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3Cl CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3SCH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3SCH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3__________________________________________________________________________
TABLE 11__________________________________________________________________________ ##STR119##R.sub.1 Q R Z X Y__________________________________________________________________________OCH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3S(O)CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3S(O)CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 SCH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 (CH.sub.2).sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 (CH.sub.2).sub.2 SCH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 S(O)CH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 S(O)CH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 SO.sub. 2 CH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 SO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 C(O)N(CH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 C(O)N(CH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CN H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CN H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CHNOCH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CHNOCH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 C(CH.sub.3)NOCH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 C(CH.sub.3)NOCH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 ##STR120## H CH CH.sub.3 OCH.sub.3OCH.sub.3 ##STR121## H N CH.sub.3 OCH.sub.3OCH.sub.3 ##STR122## H CH CH.sub.3 OCH.sub.3OCH.sub.3 ##STR123## H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CH(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CH(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CH(SCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CH(SCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 C(CH.sub.3)(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 C(CH.sub.3)(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3OCH.sub.3 (CH.sub.2).sub.2 CH(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3OCH.sub.3 (CH.sub.2).sub.2 CH(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3__________________________________________________________________________
TABLE 12__________________________________________________________________________ ##STR124##R.sub.1 Q R Z X Y__________________________________________________________________________OCH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3OCH.sub.3 CH.sub.2 OCH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3S(O)CH.sub.3 CH.sub.2 OCH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub. 3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3N(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 CH.sub.3 N CH.sub.3 OCH.sub.3CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3S(O)CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3S(O)CH.sub.3 (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3N(CH.sub.3).sub.2 (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 SCH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 (CH.sub.2).sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 (CH.sub.2).sub.2 SCH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 S(O)CH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 S(O)CH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 SO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 SO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 C(O)N(CH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 C(O)N(CH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CN H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CN H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CHNOCH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CHNOCH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 C(CH.sub.3)NOCH.sub.3 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 C(CH.sub.3)NOCH.sub.3 H N CH.sub.3 OCH.sub.3OCH.sub.3 ##STR125## H CH CH.sub.3 OCH.sub.3OCH.sub.3 ##STR126## H N CH.sub.3 OCH.sub.3OCH.sub.3 ##STR127## H CH CH.sub.3 OCH.sub.3OCH.sub.3 ##STR128## H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CH(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CH(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CH(SCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CH(SCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 C(CH.sub.3)(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 C(CH.sub.3)(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3OCH.sub.3 (CH.sub.2).sub.2 CH(OCH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3OCH.sub.3 (CH.sub.2).sub.2 CH(OCH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3__________________________________________________________________________
TABLE 13______________________________________ ##STR129##R.sub.1 Q A______________________________________H CH.sub.2 OCH.sub.3 ##STR130##H CH.sub.2 OCH.sub.3 ##STR131##H CH.sub.2 OCH.sub.3 ##STR132##H CH.sub.2 OCH.sub.3 ##STR133##H CH.sub.2 OCH.sub.3 ##STR134##H CH.sub.2 OCH.sub.3 ##STR135##H CH.sub.2 OCH.sub.3 ##STR136##H CH.sub.2 OCH.sub.3 ##STR137##H CH.sub.2 OCH.sub.3 ##STR138##H CH.sub.2 OCH.sub.3 ##STR139##______________________________________
TABLE 14______________________________________ ##STR140##R.sub.1 O A______________________________________H CH.sub.2 OCH.sub.3 ##STR141##H CH.sub.2 OCH.sub.3 ##STR142##H CH.sub.2 OCH.sub.3 ##STR143##H CH.sub.2 OCH.sub.3 ##STR144##H CH.sub.2 OCH.sub.3 ##STR145##H CH.sub.2 OCH.sub.3 ##STR146##H CH.sub.2 OCH.sub.3 ##STR147##H CH.sub.2 OCH.sub.3 ##STR148##H CH.sub.2 OCH.sub.3 ##STR149##H CH.sub.2 OCH.sub.3 ##STR150##______________________________________
TABLE 15__________________________________________________________________________ ##STR151##R.sub.1 O R Z X Y m.p. (.degree.C.)__________________________________________________________________________H CH.sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3H CH.sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.3 H CH Cl OCH.sub.3H CH.sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3H CH.sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3H CH.sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H (CH.sub.2).sub.2 OCH.sub.3 H CH CH.sub.3 CH.sub.3H (CH.sub.2 ).sub.2 OCH.sub.3 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 OCH.sub.3 H CH OCH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 OCH.sub.3 H CH Cl OCH.sub.3H (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 CH.sub.3H (CH.sub.2).sub.2 OCH.sub.3 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 OCH.sub.3 H N OCH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 OCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 SCH.sub.3 H CH CH.sub.3 CH.sub.3H CH.sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 SCH.sub.3 H CH OCH.sub.3 OCH.sub.3H CH.sub.2 SCH.sub.3 H CH Cl OCH.sub.3H CH.sub.2 SCH.sub.3 H N CH.sub.3 CH.sub.3H CH.sub.2 SCH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 SCH.sub.3 H N OCH.sub.3 OCH.sub.3H CH.sub.2 SCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H (CH.sub.2).sub.2 SCH.sub.3 H CH CH.sub.3 CH.sub.3H (CH.sub.2).sub.2 SCH.sub.3 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 SCH.sub.3 H CH OCH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 SCH.sub.3 H CH Cl OCH.sub.3H (CH.sub.2).sub.2 SCH.sub.3 H N CH.sub.3 CH.sub.3H (CH.sub.2).sub.2 SCH.sub.3 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 SCH.sub.3 H N OCH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 SCH.sub.3 H N OCH.sub.2 CH.sub.3 NHCH.sub.3H CH.sub.2 S(O)CH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 S(O)CH.sub.3 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 S(O)CH.sub.3 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 S(O)CH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 SO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 SO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 SO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 SO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 CO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 CO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CO.sub.2 CH.sub.3 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CO.sub.2 CH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 C(O)N(CH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H CH.sub.2 C(O)N(CH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 C(O)N(CH.sub.3).sub.2 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 C(O)N(CH.sub.3).sub.2 H N CH.sub.3 OCH.sub.3H CH.sub.2 CN H CH CH.sub.3 OCH.sub.3H CH.sub.2 CN H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CN H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CN H N CH.sub.3 OCH.sub.3H CH.sub.2 CHNOCH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 CHNOCH.sub.3 H N CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CHNOCH.sub.3 H CH CH.sub.3 OCH.sub.3H (CH.sub.2).sub.2 CHNOCH.sub.3 H N CH.sub.3 OCH.sub.3H CH.sub.2 C(CH.sub.3 )NOCH.sub.3 H CH CH.sub.3 OCH.sub.3H CH.sub.2 C(CH.sub.3)NOCH.sub.3 H N CH.sub.3 OCH.sub.3H CH(OH)CH.sub.2 CH.sub.3 H CH CH.sub.3 CH.sub.3 108-111H CH(OH)CH.sub.2 CH.sub.3 H CH OCH.sub.3 OCH.sub.3 130-134__________________________________________________________________________
FORMULATIONS
Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:
______________________________________ Active Weight Percent* Ingredient Diluent(s) Surfactant(s)______________________________________Wettable Powders 20-90 0-74 1-10Oil Suspensions, 3-50 40-95 0-15Emulsions, Solutions,(including EmulsifiableConcentrates)Aqueous Suspension 10-50 40-84 1-20Dusts 1-25 70-99 0-5Granules and Pellets 0.1-95 5-99.9 0-15High Strength 90-99 0-10 0-2Compositions______________________________________ *Active ingredient plus at least one of a Surfactant or a Diluent equals 100 weight percent.
Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing.
Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers". 2nd Ed., Dorland Books, Caldwell, N.J., but other solids, either mined or manufactured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0.degree. C. "McCutcheon's Detergents and Emulsifiers Annual". MC Publishing Corp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc.
The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff.
For further information regarding the art of formulation, see for example:
H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41;
R. W. Lickenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182;
H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4;
G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pp. 81-96; and
J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.
In the following examples, all parts are by weight unless otherwise indicated.
EXAMPLE 2
______________________________________Wettable Powder______________________________________N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3- 80%(methylthiomethyl)-2-pyridinesulfonamidesodium alkylnaphthalenesulfonate 2%sodium ligninsulfonate 2%synthetic amorphous silica 3%kaolinite 13%______________________________________
The ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, reblended, and packaged.
EXAMPLE 3
______________________________________Wettable Powder______________________________________N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3- 50%(methylthiomethyl)-2-pyridinesulfonamidesodium alkylnaphthalenesulfonate 2%low viscosity methyl cellulose 2%diatomaceous earth 46%______________________________________
The ingredients are blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in diameter. The product is reblended before packaging.
EXAMPLE 4
______________________________________Granule______________________________________Wettable Powder of Example 3 5%attapulgite granules 95%(U.S.S. 20-40 mesh: 0.84-0.42 mm)______________________________________
A slurry of wettable powder containing 25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged.
EXAMPLE 5
______________________________________Extruded Pellet______________________________________N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3- 25%(methylthiomethyl)-2-pyridinesulfonamideanhydrous sodium sulfate 10%crude calcium ligninsulfonate 5%sodium alkylnaphthalenesulfonate 1%calcium/magnesium bentonite 59%______________________________________
The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled.
EXAMPLE 6
______________________________________Low Strength Granule______________________________________N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3- 1%(methylthiomethyl)-2-pyridinesulfonamideN,N-dimethylformamide 9%attapulgite granules 90%(U.S.S. 20 to 40 sieve)______________________________________
The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double-cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged.
EXAMPLE 7
______________________________________Granule______________________________________N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3- 80%(methylthiomethyl)-2-pyridinesulfonamidewetting agent 1%crude ligninsulfonate salt (containing 10%5-20% of the natural sugars)attapulgite clay 9%______________________________________
The ingredients are blended and milled to pass through a 100 mesh screen. This material is then added to a fluid bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized material. The fluidization and spraying are continued until granules of the desired size range are made. The spraying is stopped, but fluidization is continued, optionally with heat, until the water content is reduced to the desired level, generally less than 1%. The material is then discharged, screened to the desired size range, generally 14-100 mesh (1410-149 microns), and packaged for use.
EXAMPLE 8
______________________________________Low Strength Granule______________________________________N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3- 1%(methylthiomethyl)-2-pyridinesulfonamideN,N-dimethylformamide 9%attapulgite granules 90%(U.S.S. 20 to 40 sieve)______________________________________
The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged.
EXAMPLE 9
______________________________________Aqueous Suspension______________________________________N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3- 40%(methylthiomethyl)-2-pyridinesulfonamidepolyacrylic acid thickener 0.3%dodecylphenol polyethylene glycol ether 0.5%disodium phosphate 1%monosodium phosphate 0.5%polyvinyl alcohol 1.0%water 56.7%______________________________________
The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size.
EXAMPLE 10
______________________________________Solution______________________________________N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3- 5%(methylthiomethyl)-2-pyridinesulfonamide, ammoniumsaltwater 95%______________________________________
The salt is added directly to the water with stirring to produce the solution, which may then be packaged for use.
EXAMPLE 11
______________________________________High Strength Concentrate______________________________________N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3- 99%(methylthiomethyl)-2-pyridinesulfonamidesilica aerogel 0.5%synthetic amorphous silica 0.5%______________________________________
The ingredients are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening). The concentrate may be formulated further if necessary.
EXAMPLE 12
______________________________________Wettable Powder______________________________________N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3- 90%(methylthiomethyl)-2-pyridinesulfonamidedioctyl sodium sulfosuccinate 0.1%synthetic fine silica 9.9%______________________________________
The ingredients are blended and ground in a hammer-mill to produce particles essentially all below 100 microns. The material is sifted through a U.S.S. No. 50 screen and then packaged.
EXAMPLE 13
______________________________________Wettable Powder______________________________________N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3- 40%(methylthiomethyl)-2-pyridinesulfonamidesodium ligninsulfonate 20%montmorillonite clay 40%______________________________________
The ingredients are thoroughly blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size. The material is reblended and then packaged.
EXAMPLE 14
______________________________________Oil Suspension______________________________________N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3- 35%(methylthiomethyl)-2-pyridinesulfonamideblend of polyalcohol carboxylic 6%esters and oil soluble petroleumsulfonatesxylene 59%______________________________________
The ingredients are combined and ground together in a sand mill to produce particles essentially all below 5 microns. The product can be used directly, extended with oils, or emulsified in water.
EXAMPLE 15
______________________________________Dust______________________________________N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3- 10%(methylthiomethyl)-2-pyridinesulfonamideattapulgite 10%Pyrophyllite 80%______________________________________
The active ingredient is blended with attapulgite and then passed through a hammer-mill to produce particles substantially all below 200 microns. The ground concentrate is then blended with powdered pyrophyllite until homogeneous.
EXAMPLE 16
______________________________________Oil Suspension______________________________________N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3- 25%(methylthiomethyl)-2-pyridinesulfonamidepolyoxyethylene sorbitol hexaoleate 5%highly aliphatic hydrocarbon oil 70%______________________________________
The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water.
UTILITY
Test results indicate that the compounds of the present invention are highly active preemergent or postemergent herbicides or plant growth regulants. Many of them have utility for broad-spectrum pre- and or post-emergence weed control in areas where complete control of all vegetation is desired, such as around fuel storage tanks, industrial storage areas, parking lots, drive-in theaters, around billboards, highway and railroad structures. Some of the compounds have utility for selective weed control in crops such as rice, wheat, barley, corn, soybeans and cotton. Alternatively, the subject compounds are useful to modify plant growth.
The rates of application for the compounds of the invention are determined by a number of factors, including their use as plant growth modifiers or as herbicides, the crop species involved, the types of weeds to be controlled, weather and climate, formulations selected, mode of application, amount of foliage present, etc. In general terms, the subject compounds should be applied at levels of around 0.01 to 10 kg/ha, the lower rates being suggested for use on lighter soils and/or those having a low organic matter content, for selective weed control or for situations where only short-term persistence is required.
The compounds of the invention may be used in combination with any other commercial herbicide; examples of which are those of the triazine, triazole, uracil, urea, amide, diphenylether, carbamate and bipyridylium and imidazolinone types.
The herbicidal properties of the subject compounds were discovered in a number of greenhouse tests. The test procedures and results follow.
__________________________________________________________________________Compounds ##STR152##Compound O R.sub.1 R X Y Z__________________________________________________________________________ 1 CH.sub.2 SCH.sub.3 H H CH.sub.3 CH.sub.3 CH 2 CH.sub.2 SCH.sub.3 H H CH.sub.3 OCH.sub.3 CH 3 CH.sub.2 SCH.sub.3 H H OCH.sub.3 OCH.sub.3 CH 4 CH.sub.2 SCH.sub.3 H H Cl OCH.sub.3 CH 5 CH.sub.2 SO.sub.2 CH.sub.3 H H OCH.sub.3 OCH.sub.3 CH 6 CH.sub.2 SO.sub.2 CH.sub.3 H H Cl OCH.sub.3 CH 7 CH.sub.2 SO.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 CH 8 CH.sub.2 SO.sub.2 CH.sub.3 H H CH.sub.3 OCH.sub.3 CH 9 CH.sub.2 OCH.sub.3 H H OCH.sub.3 OCH.sub.3 CH10 CH.sub.2 OCH.sub.3 H H CH.sub.3 OCH.sub.3 N11 CH.sub.2 OCH.sub.3 H H OCH.sub.3 OCH.sub.3 N12 CH.sub.2 OCH.sub.3 H H Cl OCH.sub.3 CH13 CH.sub.2 OCH.sub.3 H H OC.sub.2 H.sub.5 NHCH.sub.3 N14 CH.sub.2 OCH.sub.3 6-Cl H OCH.sub.3 OCH.sub.3 CH15 CH.sub.2 OCH.sub.3 6-Cl H CH.sub.3 OCH.sub.3 CH16 CH.sub.2 OCH.sub.3 6-Cl H Cl OCH.sub.3 CH17 CH.sub.2 OCH.sub.3 6-Cl H CH.sub.3 CH.sub.3 CH18 CH.sub.2 OCH.sub.3 6-Cl H OCH.sub.3 OCH.sub.3 N19 CH.sub.2 OCH.sub.3 6-Cl H CH.sub.3 OCH.sub.3 N20 CH.sub.2 OCH.sub.3 6-Cl H OC.sub.2 H.sub.5 NHCH.sub.3 N21 CH.sub.2 OCH.sub.3 6-Cl CH.sub.3 CH.sub.3 OCH.sub.3 N22 CH.sub.2 OCH.sub.3 6-Cl CH.sub.3 OCH.sub.3 OCH.sub.3 CH23 CH.sub.2 OCH.sub.3 5-Cl H OCH.sub.3 OCH.sub.3 CH24 CH.sub.2 OCH.sub.3 5-Cl H CH.sub.3 OCH.sub.3 CH25 CH.sub.2 OCH.sub.3 5-Cl H OCH.sub.3 OCH.sub.3 N26 CH.sub.2 OCH.sub.2 CH.sub.3 H H OCH.sub.3 OCH.sub.3 CH27 CH.sub.2 OCH.sub.2 CH.sub.3 H H OCH.sub.3 OCH.sub.3 N28 CH.sub.2 OCH.sub.2 CH.sub.3 H H CH.sub.3 OCH.sub.3 N29 CH.sub.2 OCH.sub.2 CH.sub.3 H H CH.sub.3 OCH.sub.3 CH30 CH.sub.2 SCH.sub.2 CH.sub.3 H H CH.sub.3 OCH.sub.3 CH31 CH.sub.2 SCH.sub.2 CH.sub.3 H H OCH.sub.3 OCH.sub.3 CH32 CH.sub.2 SCH.sub.2 CH.sub.3 H H CH.sub.3 OCH.sub.3 N33 CH.sub.2 SCH.sub.2 CH.sub.3 H H Cl OCH.sub.3 CH34 CH.sub.2 SCH.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 CH35 CH.sub.2 SCH.sub.2 CH.sub.2 CH.sub.3 H H CH.sub.3 OCH.sub.3 CH36 CH.sub.2 SCH.sub.2 CH.sub.2 CH.sub.3 H H OCH.sub.3 OCH.sub.3 CH37 CH.sub.2 SCH.sub.2 CH.sub.2 CH.sub.3 H H CH.sub.3 OCH.sub.3 N38 CH.sub.2 SCH.sub.2 CH.sub.2 CH.sub.3 H H Cl OCH.sub.3 CH39 CH.sub.2 SCH.sub.2 CH.sub.2 CH.sub.3 H H CH.sub.3 OCH.sub.3 CH40 CH(CH.sub.3)SCH.sub.3 H H OCH.sub.3 OCH.sub.3 N41 CH(CH.sub.3)SCH.sub.3 H H CH.sub.3 OCH.sub.3 N42 CH(CH.sub.3)SCH.sub.3 H H OCH.sub.3 OCH.sub.3 CH43 CH(CH.sub.3)SCH.sub.3 H H Cl OCH.sub.3 CH44 CH(CH.sub.3)SCH.sub.3 H H CH.sub.3 CH.sub.3 CH45 CH(CH.sub.3)SCH.sub.3 H H CH.sub.3 OCH.sub.3 CH46 CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H H OCH.sub.3 OCH.sub.3 N47 CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H H OCH.sub.3 OCH.sub.3 CH48 CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H H CH.sub.3 OCH.sub.3 CH49 CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H H CH.sub.3 OCH.sub.3 N50 CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H H OCH.sub.3 OCH.sub.3 CH51 CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H H OCH.sub.3 OCH.sub.3 N52 CH.sub.2 C(O)N(CH.sub.3).sub.2 H H OCH.sub.3 OCH.sub.3 CH53 CH(OH)CH(CH.sub.3).sub.2 H H CH.sub.3 CH.sub.3 CH54 CH(OH)CH(CH.sub.3).sub.2 H H CH.sub.3 OCH.sub.3 CH55 CH(OH)CH(CH.sub.3).sub.2 H H OCH.sub.3 OCH.sub.3 CH56 CH(OH)CH(CH.sub.3).sub.2 H H CH.sub.3 OCH.sub.3 N57 CH(OH)CH(CH.sub.3).sub.2 H H OCH.sub.3 OCH.sub.3 N58 CH(OH)CH(CH.sub.3).sub.2 H H Cl OCH.sub.3 CH59 CH.sub.2 CO.sub.2 CH.sub.3 H H OCH.sub.3 OCH.sub.3 CH60 CH.sub.2 CO.sub.2 CH.sub.3 H H CH.sub.3 OCH.sub.3 CH61 CH.sub.2 CO.sub.2 CH.sub.3 H H Cl OCH.sub.3 CH__________________________________________________________________________
TEST A
Seeds of crabgrass (Digitaria sp.), barnyard-grass (Echinochloa crusgalli), giant foxtail (Setaria Faberi), wild oats (Avena fatua), cheatgrass (Bromus secalinus), velvetleaf (Abutilon theophrasti), morningglory (Ipomoea spp.), cocklebur (Xanthium pennsylvanicum), sorghum, corn, soybean, sugarbeet, cotton, rice, wheat, barley and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with the test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were treated with a soil/foliage application. At the time of treatment, the plants ranged in height from 2 to 18 cm. Treated plants and controls were maintained in a greenhouse for sixteen days, whereupon all species were compared to controls and visually rated for response to treatment. The ratings are based on a numerical scale extending from 0=no injury, to 10=complete kill. The accompanying descriptive symbols have the following meanings:
C=chlorosis or necrosis;
B=burn
D=defoliation
E=emergence inhibition;
G=growth retardation;
H=formative effects;
U=unusual pigmentation
X=axillary stimulation; and
S=albinism
6Y=abscised buds or flowers.
TABLE A CMPD 1 CMPD 2 CMPD 3 CMPD 4 CMPD 5 CMPD 6 CMPD 7 CMPD 8 RATE = KG/HA 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 POSOL COTTON 0 0 10C 9G 9C 4C,9H 3C,7H 2C 0 0 2C,5G 0 2C,9G 2C,9H 1H 0 MORNING GLORY 3C,5G 1C 4C,9G 3C,7G 9C 5C,9G 3C,5H 1C 3H 0 4C,8G 3C,5G 10C 4C,9G 3C,7H 3G COCKLEBUR 2C,8G 2H 3C,8H 7H 10C 4C,9G 7H 7G 0 0 4C,8H 2H 9C 3C,9H 1H 1H NUTSEDGE 0 0 3C,7G 2G 5C,9G 9G 0 0 3G 0 2C,6G 0 3C,9G 3C,8G 2C 0 CRABGRASS 0 0 5G 2G 6C,9G 3C,8G 3C,5G 2G 0 0 6G 0 3C,8G 3C,6G 0 0 BARNYARD GRASS 6H 0 3C,7H 3H 9C 9C 3C,9G 2C,3H 0 0 3C,9H 2C,3G 9C 9C 3C,8H 3H WILD OATS 2G 0 3C,6G 0 5C,9G 2C,8G 5G 0 0 0 9G 2C,7G 4C,9G 2C,9G 2C 0 WHEAT 3G 0 9G 5G 9C 4C,9G 5G 5G 5G 0 9G 6G 9C 5C,9G 3G 0 CORN 0 0 2C,4G 0 10C 3C,9H 0 0 0 0 1C,3G 0 3C,9G 9G 1C 0 SOYBEAN 0 0 3C,8G 6G 6C,9G 4C,9G 2C,2H 0 0 0 4C,8H 3C,6G 6C,9G 4C,9H 2H 0 RICE 3C,9G 3G 4C,9G 7G 9C 4C,9G 5C,9G 2G 2C,7G 0 5C,9G 3C,6G 9C 9C 3C,9G 2C,2G SORGHUM 2C,5G 0 3C,6H 2G 9C 5C,9G 5C,9G 7G 2G 0 3C,9G 5G 3C,9G 2C,9G 4C,9G 3C,9H CHEATGRASS 8G 0 4C,9G 2C,8G 9C 6C,9G 9G 6G 8G 4G 2C,9G 7G 9C 9C 6G 2G SUGAR BEETS 1C 0 3C,8H 2H 9C 9C 3C,7H 2G 0 0 4C,9G 3C,7G 10C 10C 3C,8H 2H VELVETLEAF 3C,7G 2H 3C,8G 7G 10C 9C 7G 2C,3G 0 0 3C,8H 4G 9C 4C,9G 0 0 GIANT FOXTAIL 3C,4G 0 4C,9G 3C,8G 10C 9C 3C,9G 2C,2H 5G 0 3C,8G 2C,5G 9C 4C,9G 3G 0 BARLEY 0 0 7G 5G 9C 5C,9G -- 5G 0 0 3C,8G 2C,5G 6C,9G 3C,9G 3C,4G 0 PRSOL COTTON 0 0 2G 0 7G 0 0 0 0 0 0 2C,6G 5G 0 0 MORNING GLORY 0 0 0 0 8G 0 0 0 0 2G 0 2C,8G 2C,7H 1C 0 COCKLEBUR 0 0 2G 0 3C,4H 2H -- 0 0 0 0 3C,8G 2C,2H 8H 4G NUTSEDGE 0 0 0 0 2C,9G 0 0 0 0 0 0 10E 6C,9G 0 0 CRABGRASS 0 0 -- 0 9H 2G 0 0 0 0 0 3C,7G 2C,5G 0 0 BARNYARD GRASS 0 0 2G 0 9H 0 0 0 0 0 0 3C,9H 2C,2H 2C,2G 0 WILD OATS 0 0 0 0 6G 0 0 0 0 0 0 3C,8G 2C,8G 3G 0 WHEAT 0 0 0 0 8G 0 0 0 0 0 0 9H 7G 2G 0 CORN 0 0 0 0 3C,9H 0 0 0 0 0 0 3C,9H 3C,5G 0 0 SOYBEAN 0 0 2G 0 3C,8G 0 0 0 0 2G 0 3C,8H 5H 2C 0 RICE 4G 0 0 0 9H 2C,7G 0 2G 0 2G 0 5C,9G 4C,9H 3C,3G 0 SORGHUM 0 0 0 0 3C,9H 3C,7G 0 0 0 0 0 2C,9G 3C,9H 3C,8H 3C,5G CHEATGRASS 0 0 0 0 9H 2G 0 3G 0 0 0 3C,9G 8G 2G 0 SUGAR BEETS 2G 0 0 0 5C,9G 2H 0 0 0 0 0 5C,9G 4C,8G 3H 3H VELVETLEAF 0 0 0 0 3C,4G 1H 0 0 0 0 0 3C,8G 2C 0 0 GIANT FOXTAIL 0 0 3G 0 9H 2G 0 0 0 0 0 9H 9H 0 0 BARLEY 0 0 0 0 7G 0 0 0 0 0 0 2C,8G 8G 2C,2G 0 CMPD 9 CMPD 10 CMPD 11 CMPD 12 CMPD 13 CMPD 14 CMPD 15 CMPD 16 RATE = KG/HA 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 POSOL COTTON 9C 9C 4C,9G 4C,9G 3C,9H 3C,8H 9C 9C 3C,7H 7H 9C 3C,8G 9C 4C,9G 2C,7G 3G MORNING GLORY 10C 5C,9H 9C 3C,9G 9C 3C,8H 10C 10C 3C,7G 3C,3G 10C 5C,9G 9C 3C,7G 4C,8G 3C,7H COCKLEBUR 10C 9C 9C 3C,8H 10C 3C,8H 9C 2C,6G 10C 1C,1H 10C 3C,9G 10C 4C,9G 10C 2C,5G NUTSEDGE -- -- 10C 2G 10C 0 10C 3C,8G 2G 0 9C 3C,9G 4C,9G 3C,9G 5G 0 CRABGRASS 3C,9G 6G 9C 5G 3C,8G 2H 6C,9G 0 3C,6G 0 3C,6G 3G 6G 3G 0 0 BARNYARD GRASS 9C 9C 9C 3C,9H 9C 3C,7H 4C,9H 3C,8H 5C,9G 3C,6H 4C,9G 8H 9H 3C,8H 3G 0 WILD OATS 3C,9G 9G 5C,9G 4C,9G 4C,9G 8G 6G 2C,3G 2C,8G 3C,7G 3C,8G 0 3C,9G 0 0 0 WHEAT 5C,9G 9G 5C,9G 4C,9G 5C,9G 7G 7G 2G 9G 5C,9G 6G 0 3C,6G 0 0 0 CORN 3U,9G 9G 9C 9C 9C 5C,9G 9H 2C,5G 9C 9C 4U,9G 3C,8H 3C,9G 3C,8H 2G 0 SOYBEAN 9C 9C 4C,9G 5C,9G 9C 5C,9G 4C,9G 3C,7H 5C,9G 3C,9H 9C 5C,9G 5C,9G 5C,9G 2C,8G 2H RICE 9C 5C,9G 9C 9C 6C,9G 5C,9G 4C,9G 7G 5C,9G 5C,9G 9C 5G 2C,8G 6G 3G 2G SORGHUM 3C,9G 9G 9C 4C,9G 5C,9G 2C,9G 5C,9G 4C,9H 9G 9G 3C,7G 2C,2H 3C,9H 2C 2C,2G 2G CHEATGRASS 9C 9C -- -- -- -- -- -- -- -- 9G 3G 3C,9G 3G 0 0 SUGAR BEETS 9C 5C,9H 9C 9C 9C 3C,7H 9C 5C,9G 3C,7H 3H 9C 9C 9C 5C,9G 5C,9G 4C,9G VELVETLEAF 10C 10C 4C,9G 2C,7G 5C,9H 3C,5H 9C 7G 3C,7H 3G 9C 3C,8G 10C 6G 2G 0 GIANT FOXTAIL 5C,9G 3C,9G 5G 0 0 0 2C,3G 0 3C,8G 2C,3G 3C,8G 0 4G 0 0 0 BARLEY 3C,8G 2C,8G 4C,8G 5G 9C 8G 5G 3G 3C,9G 3C,7G 3C,7G 2G 3C,5G 0 0 0 DOWNY BROME -- -- 9C 9C 5C,9G 2C,8G 5C,9G 2C,5G 3C,9G 3C,6G -- -- -- -- -- -- PRSOL COTTON 9G 8G 8G 0 2C,4G 2G 8G 5G 0 0 9G 5G 3C,9G 5G 5G 2G MORNING GLORY 3C,9H 8G 9G 8G 7G 6H 9G 8H 2G 0 9G 8G 9G 6G 9G 5G COCKLEBUR -- 2C,5H 3C,8H 2G 2C,2H 2G 7G 0 0 0 8G -- 9H 3C,3H 3C,4G 2G NUTSEDGE 10E 10E 8G 0 5G 0 9G 5G 0 0 10E 7G 10E 0 8G 0 CRABGRASS 9H 3C,8G 3C,8G 5G 3C,7G 2G 3C,8G 2G 3C,7G 2G 9G -- 5G 7G 3C,3G 0 BARNYARD GRASS 9H 9H 9H 3C,7G 9H 3G 9H 2C,6G 3C,8H 3G 9H 6G 9G 5G 3G 0 WILD OATS 2C,7G 7G 3C,9H 4C,8G 8H 3G 8G 2G 3C,7G 0 3C,6G 2G 2C,8G 3G 2G 0 WHEAT 9G 8G 9H 8G 9H 5G 7G 2G 5G 0 5G 0 2C,8G 0 0 0 CORN 9H 8G 3C,9G 4C,9G 9G 2C,5G 3C,8H 3C,5G 3C,5G 0 2C,9G 3C,6G 3C,9H 3C,7G 5G 0 SOYBEAN 9H 2C,5G 3C,8H 3C,6H 3C,7H 4H 3C,8H 3C,7G 3C,3H 1H 9H 3G 9H 3C,7H 2C,3H 0 RICE 10H 10H 10H 9H 10E 9H 10E 8G 9H 3G 8G 2G 3C,8H 4G 7G 0 SORGHUM 9H 9H 9H 4C,9G 3C,9H 8G 10H 3C,9H 3C,9H 3C,7G 3C,7G 2G 3C,9H 3C,4G 3C,5G 0 CHEATGRASS 9H 8H -- -- -- -- -- -- -- -- 6G 4G 8G 4G 3G 0 SUGAR BEETS 9C 8G 9G 9G 3C,9G 6G 9G 9G 0 3H 9G 8G 9G 8G 9G 7G VELVETLEAF 4C,9G 8G 9H 8G 3H 0 9H 3H 0 0 9G 5G 4C,9G 3C,4G 0 0 GIANT FOXTAIL 3C,9H 4G 2G 0 0 0 3C,7G 3G 3C,7G 2G 7G 5G 4G 6G 0 0 BARLEY 8G 7G 8G 3G 8H 5G 3C,7H 2G 7G 0 3C,6G 2G 2C,8G 3C,5G 0 0 DOWNY BROME -- -- 9H 6G 8H 3G 8G 7G 8G 2G -- -- -- -- -- -- CMPD 17 CMPD 18 CMPD 19 CMPD 20 CMPD 21 CMPD 22 CMPD 23 CMPD 24 RATE = KG/HA 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 POSOL COTTON 4C,8H 5G 3C,7G 4G 4C,9G 2G 2C,4G 0 7G 4G 2G 0 5G 0 0 0 MORNING GLORY 3C,7H 4G 4C,8G 3C,7G 5C,9G 3C,7G 3C,5G 0 3C,6G 0 3C,7G 3G 0 0 0 0 COCKLEBUR 4C,9G 2C,3H 3C,7G 0 3C,8G 2C,3G 2C 0 2C,5G 0 0 0 2G 0 0 0 NUTSEDGE 9G 0 0 0 0 0 0 0 0 0 7G 0 0 0 0 0 CRABGRASS 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 BARNYARD GRASS 2C 0 0 0 2H 0 2H 0 0 0 2C,9H 0 0 0 0 0 WILD OATS 2G 0 0 0 2C,6G 0 0 0 0 0 0 0 0 0 0 0 WHEAT 5G 0 3G 0 4G 0 0 0 0 0 0 0 0 0 0 0 CORN 3G 0 2C,6G 0 4C,9H 0 3C,8H 0 3G 0 0 0 0 0 0 0 SOYBEAN 4C,9G 3C,7G 5C,9G 3C,7G 5C,9G 4C,9G 4C,8G 0 3C,6G 2G 0 0 3C,9G 2G 0 0 RICE 9G 4G 7G 4G 6G 4G 5G 0 3G 0 3G 0 0 0 0 0 SORGHUM 4C,9H 0 0 0 2C 0 0 0 0 0 0 0 0 0 0 0 CHEATGRASS 2C,4G 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 SUGAR BEETS 5C,9G 3C,6G 9C 3C,7G 5C,9G 4C,8G 0 0 3C,6H 3C,8G 0 0 2C,5G 0 0 0 VELVETLEAF 3C,7G 0 3C,7G 2G 4C,8G 0 1C 0 2C,7G 4G 2C,8G 7G 2C,7G 2G 0 0 GIANT FOXTAIL 0 0 0 0 0 0 0 0 0 0 2G 0 0 0 0 0 BARLEY 3G 0 3C,5G 0 2C 0 2C,2G 0 0 0 0 0 0 0 0 0 PRSOL COTTON 6G 0 6G 0 6G 0 4G 0 0 0 0 0 0 0 0 0 MORNING GLORY 6G 0 9G 0 9G 0 5G 0 0 0 0 0 0 0 0 0 COCKLEBUR 2G 0 0 0 0 8G 0 0 0 0 0 0 0 0 0 0 NUTSEDGE 3G 0 3G 0 0 8G 0 0 0 -- 0 0 0 0 0 0 CRABGRASS 9G 0 -- 0 2C,3G -- 3G -- 0 0 0 0 0 0 0 0 BARNYARD GRASS 0 0 4G 2G 7H 2G 4G 0 0 0 0 0 0 0 0 0 WILD OATS 5G 0 4G -- 2G 0 2G 0 0 0 0 0 0 0 0 0 WHEAT 6G 0 7G 0 7G 0 0 0 0 0 0 0 0 0 0 0 CORN 4G 0 3C,7G 0 3C,8G 0 0 0 0 0 0 0 0 0 0 0 SOYBEAN 1H 0 3C,7H 0 3C,8G 0 4G 0 0 0 0 0 0 0 0 0 RICE 8G 0 3C,9H 0 8G 2C,5G 3G 0 0 0 0 0 0 0 0 0 SORGHUM 2C,5G 0 3G 0 3G 0 0 0 0 0 0 0 0 0 0 0 CHEATGRASS 4G 0 4G 0 2G 0 5G 0 0 0 0 0 0 0 0 0 SUGAR BEETS 8G 4G 9G 7G 7G 3G 5G 0 2G 0 0 0 0 0 0 0 VELVETLEAF 2G 0 3G 0 3C,3G 0 0 0 0 0 0 0 0 0 0 0 GIANT FOXTAIL 9G 0 7G 0 3G -- 0 0 0 0 0 0 0 0 0 0 BARLEY 6G 0 7G 0 7G 0 0 0 0 0 0 0 0 0 0 0 CMPD 25 CMPD 26 CMPD 27 CMPD 28 CMPD 29 CMPD 30 CMPD 31 CMPD 32 RATE = KG/HA 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 POSOL COTTON 0 0 4C,9G 3C,9G 3C,9H 3C,8H 4C,9H 4C,8H 4C,9G 2C,8G 5G 4G 2C,9H 1C 2G 0 MORNING GLORY 0 0 10C 10C 9C 9C 10C 9C 10C 9C,9G 3C,8G 3C,5H 9C 4C,9G 0 0 COCKLEBUR 0 0 10C 10C 9C 3C,8H 10C 9C 10C 4C,9H 7G 4G 3C,9H 4C,8H 9H 0 NUTSEDGE 0 0 10C -- 7G 0 2G 0 -- 3C,8G -- 0 3C,9G 0 -- 0 CRABGRASS 0 0 9C 2C,5G 2G 0 2C,5G 0 3C,5G 4G 0 0 3G 0 0 0 BARNYARD GRASS 0 0 9C 5C,9G 3C,9H 3C,5H 5C,9G 9C 10C 9C 3C,8G 3G 9C 5C,9G 2C,3G 0 WILD OATS 0 0 9G 8G 2C,9G 2C,8G 3C,9G 4C,9G 5C,9G 2C,3G 2C,3G 0 3C,9G 2C,5G 0 0 WHEAT 0 0 9G 8G 8G 8G 9G 4C,9G 5C,9G 2C,7G 3G 0 6G 2G 0 0 CORN 0 0 5C,9G 3C,9G 9G 3C,9H 5C,9G 9C 4C,9G 3C,9H 2G 0 3C,9G 2G 2G 0 SOYBEAN 0 0 5C,9G 5C,9G 3H,6G 1H,2G 2H,5G 0 4C,9G 3C,9G 3C,9G 3H 5C,9G 3C,7H 3G 0 RICE 0 0 9C 9C 9C 9C 9C 9C 9C 9C 6G 3G 9C 3C,8G 7G 0 SORGHUM 0 0 5C,9G 4C,9G 3C,9G 9H 4C,9G 5C,9G 4C,9G 3C,9H 3C,7G 5G 5C,9G 9G 5G 0 CHEATGRASS 0 0 9C 9C 9C 2C,7G 9C 3C,9G 9C 8G 2C,3G 0 5C,9G 2C,8G 0 0 SUGAR BEETS 0 0 9C 10C 10C 10C 10C 10C 10C 10C 5C,8G 2C,7G 10C 4C,9G 3C,5G 2C,5G VELVETLEAF -- 5G 10C 10C 4C,8H 3C,8H 9C 3C,9H 9C -- 3G 6G 9C 4C,9G 0 2C,4H GIANT FOXTAIL 0 0 5C,9G 4C,9G 2G 0 2C,3G 0 3C,9H 2H,7G 2G,3G 2G 4C,9G 4C,9G 0 0 BARLEY 0 0 9C 9G 4C,9G 7G 8G 4G 3C,8G 3G,6G 2G 0 3C,9G 3C,5G 0 0 PRSOL COTTON 0 0 9G 2C,8G 3C,6G 5G 7G 5H 8G 6G 0 0 1C 2G 0 0 MORNING GLORY 0 0 9G 9G 8H 8G 9G 8G 8H 6G 0 0 5G 2G 2C 0 COCKLEBUR 0 -- 8H 9H 3C,7H 1H 6H -- 3C,7H 7H 0 0 2H 1H 0 -- NUTSEDGE 0 0 10E 10E 0 0 5G 0 3C,8G 5G 0 0 3G 0 0 0 CRABGRASS 0 0 3C,7G 4G 2C 0 2C,4G 0 3C,5G 3C,3G 0 0 4G 0 2G 0 BARNYARD GRASS 0 0 9H 9H 3C,6G 3C,3G 9H 3C,7G 9H 9H 0 0 5G 2G 2C 0 WILD OATS 0 0 3C,7G 7G 3C,8G 3C,6G 5C,8H 3C,7G 4C,7G 3C,7G 0 0 2C,3G 0 0 0 WHEAT 0 0 2C,9G 8G 2C,9G 7G 4C,9H 3C,8G 2C,9H 2C,7G 0 0 2G 0 0 0 CORN 0 0 3C,9G 3C,8G 3C,9G 3C,8G 3C,9G 3C,8G 3C,9H 3C,7G 0 0 3C,5G 0 2G 0 SOYBEAN 0 0 9H 5C,9H 3C,7H 2C,3G 3C,8H 2C,2G 3C,7H 3C,6G 0 0 3C,6H 2C,3H 0 0 RICE 0 0 10H 9H 10H 8G 10E 9H 9H 9H 0 0 2C,5G 2C,2G 2C 0 SORGHUM 0 0 10H 9H 5C,9H 8H 5C,9H 9H 10H 3C,9H 0 0 3C,8H 5G 0 0 CHEATGRAS S 0 0 9H 9H 9H 8G 9H 2C,7H 3C,8H 4H 0 0 7G 0 0 0 SUGAR BEETS 0 0 5C,9G 5C,9G 5C,9G 3C,7G 4C,9G 8G 3C,8G 9G 3G 0 9C 3H 0 0 VELVETLEAF 0 0 5C,9G 7H 3C,6H 1C 8H 2C,2H 3C,8G 5G 0 0 7H 2G 0 0 GIANT FOXTAIL 0 0 9H 9H 2C 0 2C,4G 0 3C,5G 3G 0 0 5G 0 2G 0 BARLEY 0 0 8G 3C,8G 9G 6G 3C,9G 3C,7G 8G 2G,5G 0 0 5G 0 0 0 CMPD 33 CMPD 34 CMPD 35 CMPD 36 CMPD 37 CMPD 38 CMPD 39 CMPD 40 RATE = KG/HA 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 POSOL COTTON 3G 0 0 0 9H 0 4C,9H 3C,6H 0 0 1C 0 2G 0 3C,9H 4C,9H MORNING GLORY 5H 0 3C,4H 1H 4C,8G 2C,6G 10C 4C,8H 0 0 3C,6G 0 2C,6G 0 9C 2C,7G COCKLEBUR 4G 1H 7H 4H 7H 2H 4C,9G 3C,6H 3H 2H 2H -- 2H 0 5C,9G 3C,9G NUTSEDGE 0 0 4G 0 -- 0 3C,8G 6G 0 0 0 0 0 0 0 0 CRABGRASS 0 0 3G 0 0 0 2C,5G 3G 3G 0 0 0 0 0 6G 0 BARNYARD GRASS 2C,4G 0 3C,4H 0 4C,8G 3G 9C 5C,9G 3C,5H 0 3C,6G 0 2C,3H 0 3C,9H 3C,4H WILD OATS 0 0 0 0 0 0 5C,9G 3C,5G 0 0 0 0 0 0 4C,9G 4C,9G WHEAT 0 0 0 0 0 0 -- 3G 0 0 0 0 0 0 9G 3C,7G CORN 0 0 5G 0 2C,5G 0 3C,9H 3G 2C,3G 0 0 0 2G 0 5C,9G 4C,9G SOYBEAN 2G 0 1H 0 3C,8G 3H 3C,9G 3C,7H 2H 1C 0 0 0 0 5C,9G 5C,9G RICE 1C 0 3C,6G 0 3C,6G 0 9C 4C,9G 6G 0 0 0 6G 0 9C 9C SORGHUM 3C,9G 0 3C,7G 3G 3C,8H 2G 5C,9G 3C,9G 2C,7G 0 3C,9G 0 8G 0 3C,9G 4C,9G CHEATGRASS 0 0 4G 0 2C,5G 0 9C 2C,9G 0 0 0 0 3G 0 -- -- SUGAR BEETS 5C,9G 0 9G 3G 3C,8H 2G 10C 4C,9G 3C,8G 3G 3C,8G 0 2C,5G 0 10C 9C VELVETLEAF 3G 0 8G 2G 8G 2G 10C 3C,8H 3G 2G 0 0 2C,5G 0 5C,9G 3C,5G GIANT FOXTAIL 0 0 0 0 2C,3G 0 3C,8G 2C,5G 2G 0 0 0 2C,4G 0 0 0 BARLEY 0 0 0 0 0 0 2C,8G 4G 0 0 0 0 0 0 4C,9G 2C,4G PRSOL COTTON 0 0 0 0 0 0 3G 0 0 0 2G 0 0 0 3G 6G MORNING GLORY 0 0 0 0 1C 0 7G 2H 0 0 3G 0 0 0 8G 2H COCKLEBUR 0 0 0 0 0 0 1C 0 0 0 0 0 0 0 3C,8H 2C,2H NUTSEDGE 0 0 0 0 0 0 6G 0 0 0 0 0 0 0 0 0 CRABGRASS 0 0 2G 0 0 0 2C 0 0 0 0 0 0 0 3C,8G 2C,5G BARNYARD GRASS 0 0 1C 0 0 0 3C,8G 0 2C 0 0 0 0 0 9H 0 WILD OATS 0 0 0 0 0 0 3C,6G 0 0 0 0 0 0 0 3C,8G 3C,6G WHEAT 0 0 0 0 0 0 7G 0 0 0 0 0 0 0 2C,8H 3C,7G CORN 0 0 2G 0 2G 0 3C,5G 0 2C,2G 0 2G 0 2G 0 3C,8H 3C,2H SOYBEAN 0 0 0 0 0 0 3C,6G 2C,2H 0 0 3G 0 0 0 3C,8G 5H RICE 0 0 0 0 0 0 3C,6G 0 0 0 0 0 0 0 9H 9G SORGHUM 0 0 0 0 0 0 9H 7H 0 0 2C,2G 0 0 0 9G 3C,8G CHEATGRASS 0 0 0 0 0 0 8G 0 2G 0 0 0 0 0 -- -- SUGAR BEETS 5G 0 8G 0 0 0 6G -- 0 0 0 0 0 0 8G 2H VELVETLEAF 0 0 0 0 0 0 3H 0 0 0 0 0 0 0 3C,8H 2G GIANT FOXTAIL 0 0 0 0 0 0 2C,6G 0 0 0 0 0 0 0 1C 0 BARLEY 0 0 0 0 0 0 2C,6G 0 0 0 0 0 0 0 3C,7H 8G DOWNY BROME -- -- -- -- -- -- 7G 3C,7G CMPD 42 CMPD 43 CMPD 44 CMPD 45 CMPD 46 CMPD 47 CMPD 48 CMPD 49 RATE = KG/HA 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.05 0.01 POSOL COTTON 4C,9G 3C,9G 3C,9G 9C 3C,9H 3C,8H 3C,5G 2G 0 0 0 0 2G 0 0 MORNING GLORY 5C,9G 2C,5G 9C 3C,8G 4C,9G 2C,2H 8G 0 0 0 3C,7H 2C 2C,2H 0 0 COCKLEBUR 4C,9G 5C,9G 5C,9G 5G 4C,9G 0 2C,2H 0 0 0 3C,3G 0 1C 0 0 NUTSEDGE 10C 0 10C 0 10C 9C 0 0 0 0 0 0 0 0 0 CRABGRASS 9C -- 2C,6G 0 0 0 5G 0 0 0 4G 0 2G 0 0 BARNYARD GRASS 5C,9H 3C,6G 3C,8H 3C,7H 5C,9G 3C,7H 3G 0 0 0 8H 5G 2C,5G 0 0 WILD OATS 5C,9G 4C,9G 4G 0 5C,9G 3C,8G 3C,7G 0 0 0 0 0 0 0 0 WHEAT 3C,8G 4C,9G 3G 0 5C,9G 3C,8G 3C,5G 0 0 0 4G 0 0 0 0 CORN 9C 5C,9G 3C,9G 2C,6G 4C,9G 3C,5G 3C,5G 0 0 0 0 0 0 0 0 SOYBEAN 5C,9G 4C,9G 3C,7G 6G 4C,9G 7G 3C,8H 2H 0 0 3C,5H 2C,2H 0 0 0 RICE 9C 9C 5C,9G 6G 5C,9G 2C,8G 7G 5G 0 0 2C,3G 0 0 0 0 SORGHUM 5C,9G 9G 9H 8G 4C,9G 3C,7G 3C,7G 2C,3G 0 0 9H 7G 2C 0 0 CHEATGRASS -- -- 0 0 5G 0 0 0 0 SUGAR BEETS 10C 9C 9C 9C 9C 3C,8G 5H 2G 0 0 0 0 0 0 0 VELVETLEAF 3C,8G 3C,7H 3C,7G 3C,6G 4C,8H 3C,7H 3H 0 0 0 3H 0 1C 0 0 GIANT FOXTAIL 9C 0 2G 0 0 0 0 0 0 0 3G 0 2G 0 0 BARLEY 4C,9G 5G 7G 4G 3C,8G 2G 7G 2G 0 0 0 0 0 0 0 DOWNY BROME 9C 9C 4C,9G 0 9C 4C,9G 7G 0 -- -- -- -- -- -- -- PRSOL COTTON 6G 3C,5G 5G 0 2G 0 5C,9G 9G 0 0 2C,9H 3C,5G 3C,6H 0 0 MORNING GLORY 0 2G 0 0 1C,1H 0 9C 4C,9G 0 0 5C,9G 4C,9G 3C,8H 0 0 COCKLEBUR 1C 2C 1H 0 0 0 9C 3C,7G 0 0 5C,9G 3C,8H 3C,7H 0 0 NUTSEDGE 0 0 4C,9G 0 0 0 5C,9G 0 0 0 3C,5G 0 0 0 0 CRABGRASS 7G 3C,7G 2C,5G 0 5G 0 3G -- 0 0 3G 0 0 0 0 BARNYARD GRASS 3C,5G 0 3C,5G 0 3C,3G 0 4C,9H 3C,7G 0 0 9C 5C,9H 8H 0 0 WILD OATS 3C,7G 2C,6G 3C,6G 0 4C,8G 2G 4C,9G 3C,7G 0 0 6G 0 0 0 0 WHEAT 8G 3C,7G 5G 0 3C,7G 3G 4C,9G 3C,7G 0 0 6G 0 0 0 0 CORN 1C 3C,7G 0 0 3C,7G 4G 3C,9H 9G 0 0 3G 0 0 0 0 SOYBEAN 6G 3C,6H 3C,5G 1H 5H 2H 5C,9G 3C,9G 2H 0 5C,9G 3C,8G 3C,7G 0 0 RICE 7G 9H 3C,8G 2G 9H 3G 9C 3C,9G 0 0 3C,9G 5G 3G 0 0 SORGHUM 9G 9G 9H 3G 4C,8G 2G 4C,9G 3C,8H 0 0 9C 9G 9G 0 0 SUGAR BEETS 7H 0 5G 0 0 3G -- -- 0 0 9G 6G 2C,9G 0 0 CHEATGRASS 10C 7G 2H 0 3C,9G 3C,8H 3C,7H 0 0 VELVETLEAF 3G 3H 2G 0 3G 0 10C 4C,8G 0 0 4C,9G 3C,8H 3C,8H 0 0 GIANT FOXTAIL 3C,7G 0 0 0 0 0 4C,9G 3G 0 0 5G 0 0 0 0 BARLEY 3G 3C,7G 7G 0 7G 3G 3C,9G 5G 0 0 5G 0 0 0 0 DOWNY BROME 7G 8G 5C,9G 4G 8G 0 9C 3C,6G -- -- -- -- -- -- -- CMPD 50 CMPD 51 CMPD 52 CMPD 53 CMPD 54 CMPD 55 CMPD 56 CMPD 57 RATE = KG/HA 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 POSOL COTTON 5C,9G 5C,9G 4C,9G 9H 4C,9G 4C,8H 8H 0 9H 3C,9H 4C,9G 2C,9H 0 0 0 0 MORNING GLORY 10C 5C,9G 9C 9C 10C 3C,7H 3C,7G 1H 5C,9G 3C,9H 5C,9G 4C,9G 2C,2H 0 1C,1H 0 COCKLEBUR 10C 2C,8G 10C 5C,9G 5C,9G 2C,3G 3C,9H 2G 5C,9G 5C,9H 9C 5C,9G 1H 0 3C,6G 2G NUTSEDGE 10C 2C,8G 0 8G 9C -- 3C,5G 0 3C,7G 2G 10C 9C 0 0 0 0 CRABGRASS 4C,8G 0 2C,6G 0 9C 0 3G 0 3G 2G 4C,8G 4G 0 0 6G 0 BARNYARD GRASS 9C 9C 9C 3C,8H 9C 3C,8H 5C,9G 3C,6H 5C,9G 3C,8H 9C 5C,9G 9C 3C,7H 4C,9H 3C,8H WILD OATS 2C,7G 2C,3G 3C,9G 3C,6G 5C,9G 3C,6G 3C,7G 3G 3C,9G 3C,7G 4C,9G 4C,9G 3C,9G 3C,5G 3C,8G 4G WHEAT 7G 7G 9G 2G 5C,9G 2C,7G 5G 0 3C,9G 9G 9C 4C,9G 6G 3G 3C,9G 3C,8G CORN 9G 9G 3C,9G 9G 9C 3C,9G 0 0 3C,9H 3C,5H 9C 5C,9H 9G 3C,3H 3C,9H 2C,2H SOYBEAN 5C,9G 3C,8G 3C,9H 5C,9G 5C,9G 4C,9G 3H 0 5C,9G 4C,9H 5C,9G 3C,9G 1H 0 2H 0 RICE 6C,9G 9C 9C 9C 10C 9C 3C,9G 7G 9C 5C,9G 9C 9C 9C 4C,9G 9C 8G SORGHUM 9G 9G 9G 4C,9G 10C 9C 3C,9G 3C,5H 4C,9G 4C,9H 9C 5C,9G 9C 3C,7G 4C,9G 3C,5G CHEATGRASS 2C,8G 2C,5G 6G 0 -- -- 3C,6G 4G 3C,9G 3C,8G 9C 3C,9G 3C,9G 5G 9G 7G SUGAR BEETS 10C 10C 9C 9C 9C 10C 7G 2H 9C 4C,8H 10C 9C 3C,5G 0 5G 0 VELVETLEAF 10C 10C 3C,8H 3C,7G 4C,9G 9C 3C,7H 3G 5C,9H 3C,7H 4C,9H 4C,9H 0 0 0 0 GIANT FOXTAIL 4C,9G 3C,9G 2G 4G 9C 3C,7G 0 0 3C,8G 3C,5G 9C 4C,8H 3C,5G 0 2G 0 BARLEY 7G 3C,7G 3C,5G 2G 9C 3C,9G 2C,8G 7G 5C,9G 3C,8G 9C 3C,9G 3C,8G 3C,5G 9G 3C,7G DOWNY BROME -- -- -- -- 9C 9C PRSOL COTTON 7G 8H 3G 0 7G 2G 0 0 3C,3G 2G 3C,9G 5G 0 0 0 0 MORNING GLORY 9G 8G 2C,5H 0 0 0 0 0 8H 0 8H 8H 0 0 0 0 COCKLEBUR 3C,6H 4G 0 0 2C,3G 0 3G 0 8H 3C,3G 9H 3C,9H 0 0 0 0 NUTSEDGE 10E 0 0 0 0 0 0 0 5G 0 10E 10E 0 0 0 0 CRABGRASS 5G 0 3G 0 2G 0 2C,3G 0 3C,6G 2C,5G 3C,8G 3C,7G 0 0 3G 0 BARNYARD GRASS 9H 3C,7G 3C,7H 5G 0 0 2G 0 3C,9H 3G 9H 9H 3G 0 3G 0 WILD OATS 2G 0 3C,8G 0 0 0 0 0 4C,7G 0 3C,8G 3G 0 0 0 0 WHEAT 4G 3G 3G 0 3G 0 0 0 3C,8G 0 3C,9G 5G 0 0 2G 0 CORN 3C,9G 3C,8G 3C,9G 3C,8G 2C,2G 0 2G 0 3C,5G 0 3C,9H 3C,7G 2C 0 2C,2G 0 SOYBEAN 4C,9G 3C,7H 3C,7H 2C,3G 3C,5G 1C 0 0 3C,6H 3C,3H 3C,8G 3C,7G 0 0 0 0 RICE 5C,9G 2C,7G 10H 9G 8G 0 0 0 3C,8H 1C 10H 9H 2C 0 3G 0 SORGHUM 3C,9G 4C,9G 3C,9G 3C,8G 3C,8G 2C,5G 3C,5G 0 4C,9H 3C,7G 5C,9H 3C,8G 2C,4G 0 2C,3G 0 CHEATGRASS 8G 2G 5G 0 -- -- 0 0 3C,9G 3C,4G 9G 7H 0 0 3G 0 SUGAR BEETS 4C,9G 8G 5C,9G 3G 0 0 3G 0 4C,9G 7G 9G 9G 0 0 2G 0 VELVETLEAF 3C,9G 8G 3C,3H 0 0 0 2G 0 7H 0 3C,8H 3C,7H 0 0 0 0 GIANT FOXTAIL 8G 6G 1C 0 7G 3G 0 0 7G 0 9H 3C,8G 0 0 0 0 BARLEY 3C,4G 2C,3G 3C,7G 2G 2C,3G 0 2G 0 3C,7G 2C,4G 9G 7G 0 0 0 0 DOWNY BROME -- -- -- -- 3G 0 CMPD 58 CMPD 59 CMPD 60 RATE = KG/HA 0.05 0.01 0.05 0.01 0.05 0.01 POSOL COTTON 4C,9H 3C,6G 9C 5C,9G 9C 4C,9H MORNING GLORY 3C,8H 3C,5G 10C 10C 10C 10C COCKLEBUR 4C,9H 3C,8G 10C 10C 10C 10C NUTSEDGE 7G 0 -- 5G 10C 5G CRABGRASS 0 0 3C,8G 3G 5G 2G BARNYARD GRASS 5C,9H 4C,9G 5C,9H 4C,9G 3C,8G 5G WILD OATS 2G 0 3C,9G 8G 9G 9G WHEAT 3G 0 3C,9G 9G 9G 9G CORN 1C,1H 0 9C 3C,9G 3C,9G 3G SOYBEAN 2H 0 5C,9G 3C,8H 5C,9G 3C,9H RICE 5C,9G 6G 9C 9C 9C 9C SORGHUM 9C 4C,9H 5C,9G 5C,9G 9G 8G CHEATGRASS 3C,5G 0 5C,9G 9C 9C 4C,9G SUGAR BEETS 4C,8H 3C,7HH 10C 10C 10C 10C VELVETLEAF 3C,7H 5G -- 10C 10C 10C GIANT FOXTAIL 0 0 10C 9C 10C 5C,9G BARLEY 2C,5G 0 3C,8G 2C,8G 3C,9G 5G PRSOL COTTON 0 0 3C,9G 8G 7H 5G MORNING GLORY 4H 0 9G 3C,8H 8H 2G COCKLEBUR -- 3C,5G 9H 3C,7H 3C,8H 2C,2G NUTSEDGE 0 0 3C,8G 0 3C,9G 0 CRABGRASS 3C,5G 2G 6G 0 7G 2G BARNYARD GRASS 9H 3G 6H 2G 3C,7G 2G WILD OATS 2G 0 3C,8G 2G 3C,8G 3C,5G WHEAT 2G 0 3C,9H 8G 3C,9H 7G CORN 0 0 3C,9H 3C,9H 3C,7H 2G SOYBEAN 3C,3H 0 4C,8G 2C,5H 3C,4H 2C,2H RICE 9H 8H 10E 10E 9H 3C,8H SORGHUM 4C,9H 8G 5C,9H 4C,9H 3C,9H 3C,8G CHEATGRASS 5G 0 9H 8H 9H 2C,8G SUGAR BEETS 4C,9H 3H 4C,9G 9G 7H 7G VELVETLEAF 0 0 3C,9H 3C,7H 3C,8H 2C,5G GIANT FOXTAIL 3G 0 9H 9H 9H 3C,8H BARLEY 5G 0 9G 7G 3C,8G 2C,6G
TEST B
Seeds of weeds and crops and purple nutsedge tubers were planted in sassafras sandy loam. Test chemicals were applied preemergence or postemergence (plants 2 to 18 cm tall) then the plantings were maintained in a greenhouse 16 days before visual ratings were made for response to treatment. Ratings were based on a 0 to 100 scale where 0=no injury and 100=complete kill. These data show that some important weeds can be selectively controlled in wheat and barley.
TABLE B__________________________________________________________________________ CMPD 14 CMPD 26 CMPD 27 CMPD 28RATE = G/HA 0062 0016 0004 0001 0062 0016 0004 0001 0062 0016 0004 0001 0062 0016__________________________________________________________________________POSTGIANT FOXTAIL 40 30 0 -- 100 80 30 0 0 0 0 0 90 30VELVETLEAF 100 100 60 30 100 100 90 60 90 80 70 50 70 50SUGAR BEETS 100 100 100 -- 100 100 100 100 100 100 50 30 100 100CRABGRASS 70 0 0 0 100 70 60 30 70 50 30 0 60 30TEAWEED 100 80 50 30 90 70 50 30 70 50 30 0 70 50JIMSONWEED 100 90 70 40 100 90 60 30 100 90 70 30 100 90RICE 80 40 20 0 100 90 60 30 100 100 100 60 90 80COCKLEBUR 100 100 100 30 100 100 90 60 100 80 30 0 100 90COTTON 100 80 0 0 70 60 50 30 60 30 0 0 70 40SOYBEAN 100 100 100 -- 100 100 100 70 100 50 0 0 70 50BARNYARD GRASS 100 100 80 40 100 100 90 60 90 30 0 0 100 70WILD OATS 40 30 20 -- 90 60 30 0 90 60 30 0 90 70MORNINGGLORY 100 80 30 0 100 100 80 60 100 80 30 0 100 90WHEAT 30 20 0 -- 100 60 30 0 100 50 0 0 90 70CASSIA 100 90 80 30 100 100 100 80 80 50 30 0 100 70JOHNSONGRASS 90 40 30 0 100 100 70 50 100 70 50 30 100 80NUTSEDGE 100 90 80 20 100 100 100 50 0 0 0 0 50 30CORN 100 90 70 -- 100 100 90 60 100 60 30 0 100 90WILD BUCKWHEAT 90 90 60 -- 100 100 100 70 100 50 0 0 100 60BLACK GRASS 80 70 40 -- 100 100 90 60 100 70 50 30 90 70RAPESEED 100 100 100 -- 100 100 100 100 100 100 100 70 100 100BARLEY 60 40 30 -- 80 50 30 0 100 60 30 0 70 30GREEN FOXTAIL 50 40 0 0 100 60 30 0 30 0 0 0 50 30CHEAT GRASS 80 70 30 -- 100 100 70 50 100 70 50 30 100 60LAMBSQUARTER 100 80 70 20 100 100 100 80 100 90 70 50 100 50CHICK WEED 100 100 80 -- 100 100 100 90 100 90 80 60 100 100DOWNY BROME__________________________________________________________________________RATE = G/HA 0062 0016 0004 0001 0062 0016 0004 0001 0250 0062 0016 0004 0250 0062__________________________________________________________________________PREGIANT FOXTAIL 30 20 0 0 100 70 30 -- 90 30 0 -- 90 40VELVETLEAF 100 90 30 0 100 100 90 80 100 100 90 60 90 80SUGAR BEETS 100 100 100 70 100 100 100 -- 100 100 70 -- 100 90CRABGRASS 80 70 50 20 100 70 30 0 70 30 0 0 90 60TEAWEED 100 90 70 30 100 90 70 50 90 60 30 0 90 70JIMSONWEED 100 100 50 30 100 90 50 30 100 90 60 30 90 80RICE 90 90 30 0 100 100 70 60 100 100 100 90 100 100COCKLEBUR 90 80 20 0 100 90 60 30 90 60 30 0 80 70COTTON 0 0 0 0 80 70 50 30 60 50 30 0 70 30SOYBEAN 60 50 20 0 100 100 50 -- 80 50 0 -- 80 60BARNYARD GRASS 30 20 0 0 100 100 90 -- 100 90 50 -- 100 90WILD OATS 60 40 30 20 90 60 30 -- 90 70 50 -- 70 50MORNINGGLORY 100 90 30 0 100 100 80 60 100 100 90 70 100 90WHEAT 20 0 0 0 100 80 50 -- 90 60 30 -- 100 70CASSIA 100 100 30 0 100 90 50 30 100 100 100 70 100 100JOHNSONGRASS 80 70 40 30 100 90 80 50 100 90 70 60 90 70NUTSEDGE 100 100 70 30 100 100 90 70 90 70 50 30 70 50CORN 100 90 20 0 100 100 30 -- 100 90 60 -- 90 70WILD BUCKWHEAT 100 90 90 60 100 100 90 -- 100 90 70 -- 90 80BLACK GRASS 100 90 60 30 100 100 90 -- 90 85 80 -- 100 100RAPESEED 100 100 100 60 100 100 90 -- 80 50 30 -- 100 90BARLEY 60 30 0 0 90 80 70 -- 100 70 30 -- 90 70GREEN FOXTAIL 60 40 30 0 100 60 30 0 70 30 0 0 70 50CHEAT GRASS 90 70 30 0 100 100 100 -- 100 100 90 -- 100 100LAMBSQUARTER 100 100 30 20 100 100 90 60 100 90 70 60 100 90CHICK WEED 90 90 80 60 100 90 80 -- 90 80 70 -- 100 100DOWNY BROME__________________________________________________________________________ CMPD 28 CMPD 50 CMPD 59 CMPD 61RATE = G/HA 0004 0001 0062 0016 0004 0001 0062 0016 0004 0001 0062 0016 0004 0001__________________________________________________________________________GIANT FOXTAIL 0 0 100 80 50 30 100 100 100 80 100 80 30 0VELVETLEAF 30 0 100 100 80 50 100 100 90 60 100 90 70 60SUGAR BEETS 100 70 100 100 100 50 100 100 80 50 100 100 70 50CRABGRASS 0 0 60 30 0 0 100 100 90 50 90 70 50 30TEAWEED 30 0 90 60 30 0 90 80 70 50 80 60 30 0JIMSONWEED 80 60 70 50 30 0 100 90 80 60 100 100 90 80RICE 70 50 100 90 60 30 90 80 70 60 90 80 70 60COCKLEBUR 70 30 100 80 30 0 100 100 100 90 100 100 90 50COTTON 0 0 80 70 50 0 100 100 90 60 90 70 50 30SOYBEAN 0 0 100 100 100 70 100 100 90 70 90 70 50 0BARNYARD GRASS 50 30 100 100 80 50 80 50 40 30 60 30 0 0WILD OATS 50 30 50 30 0 0 70 30 0 0 50 30 0 0MORNINGGLORY 70 50 100 90 80 70 100 100 70 60 100 80 70 60WHEAT 50 30 60 30 0 0 60 50 40 30 0 0 0 0CASSIA 50 0 100 90 70 30 100 100 90 80 90 60 30 0JOHNSONGRASS 60 30 70 50 30 0 100 100 90 70 100 100 80 50NUTSEDGE 0 0 100 90 60 30 100 90 60 30 70 50 30 0CORN 60 30 100 100 100 70 100 100 80 40 0 0 0 0WILD BUCKWHEAT 30 0 100 70 50 30 100 100 100 80 100 90 60 30BLACK GRASS 50 30 100 70 50 30 100 100 70 50 90 70 50 30RAPESEED 70 50 100 100 100 70 100 100 90 70 100 100 80 60BARLEY 0 0 0 0 0 0 90 70 50 30 0 0 0 0GREEN FOXTAIL 0 0 100 70 50 30 100 100 100 70 100 90 70 50CHEAT GRASS 30 0 90 60 30 0LAMBSQUARTER 30 0 100 100 100 90 90 80 70 50CHICK WEED 100 70 90 70 50 30 100 100 100 90 90 80 70 60DOWNY BROME 90 70 50 30 80 50 30 0__________________________________________________________________________RATE = G/HA 0016 0004 0250 0062 0016 0004 0250 0062 0016 0004 0250 0062 0016__________________________________________________________________________PREGIANT FOXTAIL 0 -- 100 90 70 50 100 100 100 -- 100 60 30VELVETLEAF 70 60 100 80 50 30 100 90 80 50 60 30 0SUGAR BEETS 80 -- 100 100 90 -- 90 80 60 -- 50 30 0CRABGRASS 30 0 100 80 30 0 100 90 70 50 80 50 30TEAWEED 50 30 100 90 70 50 90 80 70 50 60 30 0JIMSONWEED 50 30 100 90 80 70 100 90 80 70 70 50 30RICE 90 70 100 100 100 70 100 100 90 85 100 100 100COCKLEBUR 50 30 90 70 50 30 90 80 70 50 80 30 0COTTON 0 0 70 50 30 0 90 80 60 -- 40 0 0SOYBEAN 0 -- 90 70 50 0 80 30 0 -- 0 0 0BARNYARD GRASS 60 -- 100 90 80 70 100 100 70 -- 60 30 0WILD OATS 30 -- 80 50 30 -- 70 50 30 -- 0 0 0MORNINGGLORY 80 60 100 90 70 60 100 90 85 80 90 60 0WHEAT 50 -- 50 30 0 -- 70 30 0 -- 50 30 0CASSIA 70 50 100 90 60 30 100 90 80 30 70 30 0JOHNSONGRASS 50 30 100 90 70 50 100 95 90 -- 100 100 90NUTSEDGE 30 0 100 90 50 30 100 90 80 50 60 50 30CORN 30 -- 90 70 30 -- 90 70 0 -- 0 0 0WILD BUCKWHEAT 50 -- 90 80 70 -- 70 50 30 -- 0 0 0BLACK GRASS 90 -- 100 100 90 -- 90 80 70 -- 90 60 30RAPESEED 30 -- 100 90 80 -- 70 50 30 -- 100 30 0BARLEY 50 -- 90 70 30 -- 0 0 0 -- 30 0 0GREEN FOXTAIL 30 0 100 90 70 50 100 100 100 80 100 70 30CHEAT GRASS 80 -- 100 90 60 --LAMBSQUARTER 80 50 100 100 90 80 100 100 90 70 90 70 50CHICK WEED 50 -- 100 90 80 -- 90 70 50 -- 0 0 0DOWNY BROME 100 100 50 -- 70 30 0__________________________________________________________________________

Number	Name	Date
4339267	Levitt	Jul 1982
4342587	Levitt	Aug 1982
4348220	Schwing	Sep 1982
4421550	Selby et al.	Dec 1983
4456469	Adams, Jr.	Jun 1984
4487626	Zimmerman	Dec 1984
4496392	Levitt	Jan 1985
4544401	Levitt	Oct 1985
4662933	Thompson	May 1987
4740229	Selby	Apr 1988
4778512	Wexler	Oct 1988
4789465	Barnette et al.	Dec 1988

Number	Date	Country
24259	Sep 1984	AUX
13480	Jul 1980	EPX
84224	Jul 1983	EPX
117014	Aug 1984	EPX
125864	Nov 1984	EPX
155767	Sep 1985	EPX
161905	Nov 1985	EPX
164269	Dec 1985	EPX
171286	Feb 1986	EPX
187489	Jul 1986	EPX
111982	May 1987	JPX

Herbicidal pyridine sulfonamides

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