CA1252095A

CA1252095A - Herbicidal pyridinesulfonamides

Info

Publication number: CA1252095A
Application number: CA000548198A
Authority: CA
Inventors: Morris P. Rorer
Original assignee: EI Du Pont de Nemours and Co
Current assignee: EIDP Inc
Priority date: 1984-08-08
Filing date: 1987-09-29
Publication date: 1989-04-04

Abstract

Title HERBICIDAL PYRIDINESULFONAMIDES
Abstract of the Disclosure Novel pyridinesulfonamide compounds containing ortho-heterocyclic substituents such as N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(1H-1,2,4-triazol-1-yl)-3-pyridinesulfonamide display utility as herbicides and plant growth regulants. More specifically the compounds of the invention are of the formula:

I II
wherein R is H or CH3;
R1 is H, Cl, Br, SCH3, or CH3;
n is 0, 1 or 2;
W is O or S;
Q is phenyl optionally substituted with Cl, OCH3, or CH3, a saturated 5- or 6-membered ring containing one heteroatom selected from O, S, or N, or an unsaturated 5- or 6-membered ring containing 1 to 3 heteroatoms selected from 0-1 S, 0-1 O or 0-3 N and when Q is an unsaturated 5- or 6-membered ring, it may optionally be substituted by one or more groups selected from C1-C4 alkyl, halogen, C3-C4 alkenyl C1-C3 alkoxy, C1-C3 alkylthio, C3-C4 alkenyl-thio, C1-C2 haloalkoxy or C1-C2 haloa1kylthio;

X is CH3, OCH3, OCH2CH3, Cl, F, Br, I, OCF2H, CH2F, OCH2CH2F, OCH2CHF2, OCH2CF3 or CF3;
Y is H, C1-C2 alkyl, OCH3, OC2H5, CH2OCH3, NHCH, N(OCH3)CH3, N(CH3)2, CF3, SCH3, OCH2CH=CH2, OCH2C?CH, CH2OCH2CH3, OCH2CH2OCH3, CH2SCH3, , , OCF2H, SCF2H
or cyclopropyl;
m is 2 or 3;
L1 and L2 are independently O or S;
R2 is H or CH3;
R3 and R4 are independently C1-C2 alkyl;
Z is CH or N;
Y1 is O or CH2;

X1 is CH3, OCH3, OC2H5 or OCF2H;
Y2 is H or CH3;
X2 is OCH3 SCH3 or CH3;
Y3 is CH3, C2H5 or CH2CF3; and X3 is CH3 or OCH3;

provided that a) when X is Cl, F, Br or I, then Z is CH and Y
is OCH3, OC2H5, N(OCH3)CH3, NHCH3, N(CH3)2 NH2 OR OCF2H;
b) when Y is cyclopropyl, X is other than Cl, F, Br or I;
c) when Q is 1H-1,2,4-triazol-1-yl, then Z is CH;
d) when X or Y is OCF2H, then Z is CH;
e) when Q is a saturated 5- or 6-membered ring containing one nitrogen atom, it is bonded to the pyridine ring through carbon; and f) when W is S, then R is H, A is A-1, and Y is CH3, OCH3,OC2H5, CH2OCH3, C2H5, CF3, SCH3, OCH2CH=CH2, OCH2C?CH, OCH2OCH3, CH(OCH3)2 or ;
and their agriculturally suitable salts.

Description

3 ~

~ , BA-8592-A--\
HERBICIDAL PY~IDINESUk~A~
Back~round of the I en_ion Herbicidal pyridine~ulfonamides of the ~ormula Rl X
O N ~
E~2~S02t~HCN~Oz where Rl i8 H. Cl. ~r, F, Cl-C~ alkyl, Cl-C~
alkoxy, Cl-C~ alkylthio, N02 or C02R5;
and R2 is H. Cl, Br or CH3:
are disclo6ed in European Patent Application (EP-A) 13,~0.
EP-A-35,893 discloses herbicidal pyridinesulfon-amide6 of formula X

o N
Z ~ sOzUHCNH

where Rl is S50)nR3; and R2 i~ H, Cl, F, Br, CH3, OCH3, C~3, N02, CN or NH2.
EP-A-B3,975 and ~P-A 85,476 dis~lofie herbicidal benzene~ulfonamides of for~ula ~1 ~ 502NHCN~ ~ z a N
where Q is variou~ ~aturated and unsaturated 5- and 6-membered he~erocycle~.

~'' !

U.S. 4,378,991 di~loses herbicidal b~n~ene-~ulfonamides of formula ~ R
5 ~1 ~ "
N

where R is, among other va:Lue~, phenyl: and Rl i8 H, F, Cl, B~, N02, CF3, Cl-C~
alkyl, OCF3 or Cl--C4 alkoxy.
EP-A-g7,122, publi~h~d December 28, 1983, dis-closes herbicidal sulfonamide~ of formula R N Rl Z3 ~ S02NHCZNH ~ ~ E

where X i~ 0, S, NR4 or CR5=N: and ~2 i~ H, Cl-C3 alkyl, haloalkyl. alkoxy, alkylthio, alkyl~ulfinyl or alkylsul-phonyl, halogen, NO~, ~WR8, S02NR6R7 ~r CORg.
South African Patent Application 836,639 di~clo~e~ herbicidal sulfonamide~ of formula N ~ 2 R1~ S0;2NHCONH~OE

2~A R3 where ~ i8 O, S, SO, S02 or ~A may ~orm an a~ino radical NR6P.7: and R.l i5 H, halogen, Cl-C4 alkylO Cl-C4 alkoxy, Cl-C~ ~aloalkyl, Cl-C4 haloalkoxy, C2-C5 alkoxyalkoxy, Cl-C5 alkylthio, Cl-C5 alkyl-sulfinyl or Cl-C5 alkylfiulfonyl.

Summarv_of th~_Invention This invention relate6 to compounds of Formulae I and II, agriculturally suitable compo~ition& con-taining them and their method of use as preemergent and/or postemergent herbicides or plant growth regulants.
W

~1 ~ S02NHCNA ~1 ~ (CH2)n-Q
(CH2)n Q N S02NHCNA
R

I II
wherein R is H oe CH3, Rl i8 H, Cl, Br, SCH3 o~ CH3;
n is 0, 1 or 2;
W i8 0 or S;
Q i8 phenyl optionally subs~i~uted wi~h Cl, OC~3, or CH3, a saturated 5- or 6-membered ring containing one heteroatom selected from 0, S, or N, or an unsaturated 5- or 6-membered ring containing 1 to 3 heteroatoms selected from 0-1 S, 0-1 0 or 0-3 N and when Q is an unsaturated 5- or 6-membered ring, it may optionally be

3 substituted by one or more groups selected from Cl-C4 alkyl, halogen, C3-C~ alkenyl Cl-C3 alkoxy, Cl-C3 alkylthio, C3-C4 alkenyl~
~hio, Cl-C2 haloalkoxy or Cl-C2 haloalkyl~hio:
~5 N ~ ~1 N ~1 A i6 ~ O z , A-l A-2 -3 ~ ~1 /Y3 OCH3 ~ O ~ or -cHz~oN

X i8 CH3, OCH3, OCH2CH3, Cl, F, Br, I, OCF2H, CH2F, OCH2CH2F, OCH2CHF2, OCH2CF3 or CF3;
Y is H, Cl-C2 alkyl, OCH3, OC2H5, C~20CH3, 3~ ~(OCH3~CH3~ N(C~I3)2' CF3, 3 OCH2CH-CH2, 0CH2C_CH, CH20CH2CH3, OCH2CH20CH3' CH~SCH3, ~ Rz, ,~

~ L ~ / 1-~ 3 '~ L ~CH2)m, C\2 ~ , OCF2H, SCF2H
or cyclopropyl:
m i~ 2 or 3;
Ll and L2 are independently O or S:
~2 i~ H or CH3;
R3 and R4 are independently Cl-C2 alkyl;
Z is CH or ~;
Yl is 0 or C~2;
~1 i8 CH3, OCH3, OC2H5 or OCF2~;
Y2 i8 H or CH3 ~ ,r~

X2 ~ OCH3 SCH3 or CH3 Y3 i~ CH3, ~2H5 Gr ~H2~F3 and 3 i CH3 o~ OCH3 provided ~ae a~ when ~ is Cl, ~, Br or I, then Z ~ CH and Y
3~ 2H5, N(OCH3)CH3, ~HCH3, N(CH ) NH2 or OCF2H;
b) when Y i~ cyclopropyl, ~ iG other t~an C1, F, Br or I;
c) when Q iB lH-1,2,4~-triazol-1-yl, then Z il3 C~:
d) when ~ or Y i8 OCF2R, then Z ~ CH;
e) when Q i~ a saturat:ed 5- or 6-membered ring containing one nitrogen a~o~, ~t is bonded to Che pyridine ring theough carbon; and f~ wh@n W i~ S, then ~ i~ H, A is A-l, and ~ i~
3~ ~3~ 0~2H5, CR20CH3, C2H5, CF3, SC~3, O~H2CH=CH2, OCH2C-CH, OCH2CH20CH3, CH(OCH3)2 /o~
or CH
\O~
and ~heir agricul~urally suitable 5alt~.
Preferred for reasons vf grea~er ease of synthe-6iS and/or yreater h~rbicidal efficacy are:
1~ Compounds of Formulae I and II wherein R i6 El:
~ iS O;
is ~elected from the group consisting oE
,~R6 ~R6 ~ ~

o,N N~0 ~ o Q~l Q-2 Q-3 r~ ~

/ ~N N~C ' ~ ' ~ \N

Q~ Q- 5 - 6 / )~ a7 (V~ 5 /~

Q- 7 Q~8 ~_ 9 ~ N~

Q-10 Q-ll Q-12 ~ , R5 5~
.Q~ ~ Q- 1 5 2 5 R6 6 ~\R6 Q-lS Q-17 Q-18 ~5 ~5 ~ 6 ~ Q-20 Q-21 o~

R5~R7 ~;R~ It5 5 R7 .Q-23 Q~4 Q-?5 Q-26 ~R6 '~R6 ~ II5~R6 .,~
(O)n' (o)n~ (O)n' Q~:Z Q-28Q-29 0-30 ~10 ~Rlo ' ,~ (~R5 ~-31 0-32 Q-33 N~R5 ~ l,~
_3,~ Q~ Q-36 ~L5 ~5 R5 ~0 ~S ~N
N~( ~N= ( ~S~ and phenyl;

Q-37 Q~ Q-39 n' i8 0 01 1:
R5, R6 and R7 a~e independently H or CH3;

~5 iB H, CH3. C2H5, Cl-C3 alky~thio.
SCH2~H~CH2~ SC~2H~ OC~3 or OCH2CH3 ~8 ifi H or Cl:
a9 and Rlo are indep~ndently H, CH3 or ~11 aQd R12 are i~dependentiy CH3 or ~H3;

I ; 8 OD 8 Or NR13; and ~13 is H, Cl-C3 alkyi or CH2CH=CH2;
2) Compound~ o Pcefer!red 1 wh~re ~ is A~
is H. ~' i8 0 and Q i~ ~elected fro~ the group consi~ting ol Q-l, Q-2, Q-3, Q-4, Q-7, Q~8, Q-9, Q-10, Q-ll. Q-14, ~-16, Q-17. Q 18, ~-21, ~-22, ~-2~, 52-~7, ~-30. Q-33 Q-37, Q-38 and phenyl:
3) Compound~ of Prefeered 2 where ~ is CH3, OCH3, OCH2CH3 or Cl. and Y i~ CH3, ~H2CH3, OC~3, OCF2~1, CH~OCH3)2 o~
CH20CH3;

4) Compounds of Pceferred 3 where n i6 0;

5) Compounds o ~E~ r~ where Y is CH3, CH2CH3, OCH3 or OCF2H;

6) Compounds of Preferred 5 of Focmula I;

7) Compounds of Preferced 5 o~ ~ormula II;

8) Compounds of Pref erled 6 ~ere Q i8 Q-l;

9) Compounds o~ Preferred 6 where ~ i~ Q-2;

10) Compound6 of Preferred 6 where Q i6 Q-3:

11) Compounds of PreferEed 6 where Q i~ Q-4:

12) Compound6 of Preferred 6 whers Q is Q-7;

13) Compounds ~ ~~~EE~ where Q is Q-8:

14) Compound6 nf P~ E~ where Q i6 Q-9;

15) Compounds of Preferred~6 where Q is Q-10:

16~ Compounds of Preferred 6 where Q is Q-ll;
1~ Co~pound~ f ~s~~LL~ where Q i~ Q-14:
18~ Compound~ of Pceferred 6 where Q i~ ~-16;

1~) Compounds of Preferce,d 6 where Q i~ Q-17;
20) Compounds of ~Preferred 6 where Q i6 ~-18:
21) Compound~ of Preferred 6 where Q i6 Q-21;
22) Compound~ of Preferred_6 where Q is Q-2Z;
23) Compounds of Preferred 6 where Q i8 Q-2~;
24~ Compounds of Preferred 6 where Q i8 Q-27;
25) Compounds of P ferr,ed 6 where Q i~ Q-30;
26) Compounds of Preferred 6 where Q i~ Q-33;
27) Compounds of Preferred 6 where Q is Q-37;
28) Compcunds of P ferred 6 where Q ifi Q-38;
29) Compoundfi of Preferred 6 where Q i8 phenyl;
30) Compounds of Prefe~red 7 where Q i~ Q-l:
31) Compounds of Preferred 7 where Q is Q-2;
32) Compound6 of Preferred 7 whe~e Q is Q-3:
33) Compounds of Preferred 7 where Q is Q-4;
3~) Compounds of Preferred 7 where Q is Q-7;
35) Compound~ of Preferred 7 where Q is Q-8;
36) Compounds of Preferred 7 where Q i~ Q-9;
37) Compounds of Pr,eferred 7 where Q i~ Q-10;
33) Compound~ of Preferred ? where Q is Q-ll:
39) Compounds of Preferred 7 where Q is Q-14:
40) Compounds of Preferred 7 where Q i6 Q-16;
41) Compounds of Preferred 7 where Q i~ Q-17;
42) Compounds of Preferred 7 where Q i~ Q-18;
43) Compound6 of Preferred 7 where Q is Q-21:
49) Compound~ of Preferred 7 where Q i~ Q-22:
45) Compound~ of ~referred 7 where Q is Q-24;
~6) Compound~ of Preferred ? where Q i~ Q-27;
47) Compound~ of PrefeLred 7 where Q is Q-30;
4~) Compounds of Preferred 7 where Q i8 Q-33;
49) Compound~ of Preferred 7 where Q i~ Q-37;
50) Compound~ of Preferred 7 where Q i~ Q-38;
51) Compounds of Preferred 7 where Q i~ phenyl:
An exemplary compound within the scope of this invention is N-t(4,6-dimetho~ypyrimidin-2-yl)aminocar-bonyl]-2-(lH-1,2,4-triazol-1-yl)-3-pyridine~ul~onamide, m.p. 235-238~C.
g Deta~led De~criPtion~ of the Invention Synthe~i 6 The compound~ of Formulae I and II can ~e prepared by one or ~ore of the methodg ~hown below in Equation6 1, 2 and 3.
A~ ~hown in Equation 1 below, the compound~ of Formulae I and II Swherein ~ is 0~ can be prepared by treating 2~heterocyclic-3-pyridine~ulfonamide~ or 3-heterocyclic-2-pyridinesulfonamide~ of Fo~ula III
with the methyl e~ter of a pyrimidine or triazine-carbamic acid of Formula IV in the pre6ence of an equimolar quantity of trimethylaluminum.
Equation 1 Rl ~ S02NHz + CH30CN-A ~
N R II
III IV
wherein A, R, Rl, n and Q are as previously defined.

The reaction of Equ~tion 1 i~ bes~ carried out at temperature~ between 23 and 83C in an inelt ~ol-ven~ e.~. methylene chlo~ide or 1.2-dichloroethane for 12 t~ 96 hour6 under an inert atmosphere. The produc~ can be i~olated by the addition of an aqueou~
acetic a~id or hydrochloric a~id ~olution followed by extraction of the product into methylene chloride or direct filtration of a product of low ~olubility. The product can ordina~ily be purified by tri~uration wi~h solvents 6uch a8 n-butyl chloride, ethyl acetate or diethyl ether o~ by chromatography procedures. The methyl carbamates, IV, can be conveniently prepared by treat~ent of the corr*~ponding heteroaromatic a~ine~
of For~ula VII with dimethyl carbona~e or ~ethyl c~loroformate in the presence of ~ base, ~.g. ~odium hydride or pyridine.
Fu~ther detail~ of thi6 reaction an~ the prepa-eation of ~he carbamate6 of ~ormula IV can be ~ound in 5 unexamined European Patene Application (EP-A) No.
83,975 (publi~hed July 20, l9B3).
Alternatively, compound6 of Formulae I and II
(wherein W is 0) can be prepared by the ceaction of ! 6ulfonamide~ of Formula III with the phenyl ester of 10 the appropriate carbamic acid, V, in the presence of an equimolar quantity of a tertiary amine ba~e, e.g.
1,8-dia~abicyclo[5.4.0]unaec-7-ene (DBU), as ~hown below in Equation 2.
Equaeion 2 15 0 1) DBU
III ~ C6H OCN-A
5 R ) H30 ~ II
V
wherein A and R are as previou~ly defined.

The reaction of Equation 2 i~ carried out at 20 to 30C in an inert ~olvent, e.g. dioxane or aceto-ni~rile. Aqueou~ acid workup afford~ the de~iredproduc~s, according to the teac~ings of EP-A No.
70,804 (published January 26, 1983) and South African Patent Application~ 825042 and 839441. The phenyl carbamate~, V, can be prepared by treating ~he corre~ponding heteroaromatic a~ine~ of For~ula VII
with diphenyl ~arbonate or phenyl chloroforma~e in the pLe~ence of a base , e.gO 60dium hydride or pyridine.
Alfio~ compound6 of For~ulae I and II (wherei~
is 0 or S) ~ay be prepared by reacting an appropriate 2-heterocy~lic-3-pyridine~ulfonyl i60cyanate or 3-heterocyclic-2-pyriaine6ul~onyl i~ocyanate of i~ . ~.~ .. D ~
Fo~ula VI with t~e appropri~tely ~ub~t~tuted amino-heterocycle. VII, as 6hown below in E~uation 3.
Equation 3 5~ H2)nQ

N a II
VI VII
wherein A, R, Rl, n and Q are a~ previou~ly defined, and ~ is 0 or S.

The ~eaction i6 be~t performed in an inert ~olvent , e.g. methylene chloride, tetrahydrofuran, acetonitrile or toluene at 23 to 100C for one to 24 hourfi. In ca6es w~ere the products are insoluble in the reaction 601vent, they may ~e i~olat~d by simple filtration. When the product~ are 601uble, they may be isolated by evaporation of the solvent and tri-turation of the re~idue with an inert solvent , e.g.l-chlorobutane, diethyl ether or ethyl ac~tate and filtration. The products may be further purified by column chromatography procedules or ~ecrystallization.
Sulfonyl i~ocyanate~ of Formula VI aboYe may be 2 prepared, although often times in low yields, from cor~e~ponding ~ulfonamide6 of Formula II by ~ethod~
analogou~ to those de~cribed in V.S. ~,238,621 and EP-A No. a3,975 (published July 20, 1983). Thu~, by a prefe~ed method, sulfonamides are reacted with pho~-gene, in the presence of n-butyl isocyanate and a tertiary amine cataly~t, at reflux in an inert ~olvent e.g. xyle~e~. A preferred cataly~t i~ 1,4-diaza-bicyclo[2.2.2~octan~ (DABC0). Alternatively, iso-cyanate6, VI, may be prepaled by ~1) reacting 6ulfon-amide6, III, with n-butyl i~ocyanate and a ba~e , e-g.
I

potassium carbonate at reflux in an inert solvent, e.g. as 2-butanone to form a n-butylsulfonylurea; and (2) reactin~ thi6 ~ompound with pho6gene and DABC0 catalyst at ~eflux in x~lene~ solvent.
Sulfonyl isothiocyanate6 can be prepared by treatment of sulfonamide~ of Formula III with carbon disulfide and pota6sium hydroxide followed by reaction of the dipotas~ium 6alt with phosgene according to R. Hartke, Arch. Pharm., 299, 174 (1966).
2- and 3-Pyridinesulfonamide~ of Formula lII
above are impoctant intecmediate~ for the preparatio~
of the compound~ of thi~ invention, and can be pre-pared by method~ known in the literature, or simple modification~ thereof, by tho6e 6killed in the art.
Eor example, 3-pyridine6ulfonamide~ of Formula III, ~ubstituted in the 2-position with a pyrazol-l-yl, l,2,4-triazol-1-yl or imidazol-l-yl group (Q i~
Q-7, Q-16 oc Q-21) may be prepared by ~he sequence of reactions shown in Equation 4 below.
Equation 4 R ~ 2 a) Reductio ~ R ~ S02C
1 1 1 b) MEER~EIN 1 l ~
~ N ( H~)nQ ~N (CH2)nQ
VIII

I~ ) NH3 or NH40~ Rl ~ 2 2 N (CH2)nQ
~0 IIIa wherein Rl is a~ originally defined:
Q 1~ Q-7, Q-16 or Q-21; and n i~ 0, 1 or 20 .~ f~ O ~

Reaction 4(a) In this reaction 3-nitropyridine~, VIII, ar~
reduced to corre&ponding 3-aminopyridine~, fo~
example, by reaction wlth stannou6 chloride in hydro-chloric acid by conventiollal method6. Details andrefe~ences for thi~ and ol:her method~ for reducing nitropyridine~ to corre~ponding aminopyridines ~an be found in "Pyridine and Derivative~", Chapter IX, pp.
~-10, E. K].ing~berg, Ed., a part of the 6eLies "The Chemi~try of Heterocyclic Compound6~', A. ~eis~erger, Ed. The 3-nitropyridine~l, VIII, are prepared by reacting appropriate 2-ch:loro-3-nitropyridine6 with 60dium ~alt6 of appropriate pyrazole6, 1,2,4-triazole~
or imiazole~ in an inert so1vent, e.g. N,N-dimethyl-formamide (DMF), according to the teaching~ of U.S.3,489,7~1.
Reaction 4(b2 In thi~ ~eaction 3-pyEidine6u1fony1 ~hlorides, I~, are prepared by the ~eerwein ~eaction by diazo-tizing corre~ponding 3-aminopyridi~e~ with sodium nitrite in hydLochloric acid and acetic a~id, and reacting the diazonium salt~ with exceEs 6ulfur dioxide in acetic acid in the pre~ence of copper(I) ~h10ride or ~opper(II) chlorid~ cataly~. For details, refer to ana10gou~ reaction~ de~cribed in Y. ~ori~awa et al., J. Med. Chem., 23, 1376 (1980), EP-A-83,975 and H. L. Hale and F. Sowinski, ~_Q~g~
Chem., 25, 1824 (1960~.
Rea~tion 4(c~
And in this reaction, 6u1fony1 ch10rides, I~, are tran~formed to 6ulfonamide6, IIIa, by rea~tion with ~nhydrou~ ammonia in an ine~t ~olvent, e.g.
tetrahydrofuran, or by reac~ion with aqueou6 am~onium hydroxide in an iner~ ~olvent, e.g. te~rahydrofuran by ~onv~entiona1 ~et~od6. For details, ~eer ~o analogous reactions described in references cited above for Reaction 4(b).
2- and 3-Pyridinesulfonamide6 of Formula III, BUbB~ituted in the 3- and 2-po~tions respe~tlvely with 5-thio-oxadiazol-2-yl srouPS (Q i8 Q-8), ~ay be p~epared ~rom corresponding 2- and 3-~ercap~opyridyl carboxylic a~ids, X, by t~e ~equen~e of re~ction~
shown below i~ Equation 5.
Equation 5 lQ 5(a) C02H - ( i ) C12-HC:1 02CH3 Rl ~ ~ SH (ii) NH90H ~~~~~ l ~ S2NH2 ) CH30H H2S04 ~ N

_ ~I

5(b~ 0 C~HNH2 ~I H NNH H O ~
-- 2 ? 2 _~ Rl~ S02NH2 N

5(~) N-N
// \~
O~-`SR"
~II (i) KOH, CS ; H O ~
_ _ _ _ 2 ~ ~ R.-~ ~ ~So NH
(ii) ~OH. R5~ 1 ~ ~N~ 2 2 t ;~.E~
wherein Rl i~ a~ p~eviously defined;
i~ Cl-C3 alkyl, C~2CH~CH or CF2H; and ~ i Cl, Br or I.

Reaction~ 5~a) In these reactions pyridine~ulfona~ide6, ~1, are prepared by analogy wieh the teachings o~ Y. ~orisawa et al., J. ~ed. Chem., 23, 1376 (1990). The method compri~e6 (i) chlorinating appropriate 2-carboxy-3-~ercaptopyridines or 3-carboxy-2-mercaptopyridine6 in concentrated hydrochloric acid and water at about -25 to 5C to form corresponding carboxypyridyl 6ulfonyl c~loride~: (ii) aminating the i601ated ~ulfonyl chlor-ide6 with concentrated ammonium hydroxide to form thecorre~ponding carboxypyridy~l6ulfonamide~; and (iii) esterifying the6e compound~ by refluxing in methanol with ~ulfuric acid catalyst to form sulfonamide6, XI.
Alterna~ively, mercaptopyridine~, ~, may be chlorinated in the presence of pota~sium hydrogen difluoride in an inert fiolvent , e.g. water and methanol at about -30 to 0C to ~orm the corre-sponding carboxypyridyl sulfonyl fluoride6. Subse-quent reaction of these compounds with ammonia can provide the corre6ponding sulfonamide6. For fur~her detail6 cefer to analogous ceaction6 described in D. J. Brown and J. A. Ho6kins, J. Chem. So~. Perkin Tran6 I, 522 ~1972).
Reaction 5(b) Thi6 reaction i~ also run by analogy with the teaching6 of ibid. The method compri~es reacti~g pyridyl e~ter~, ~1, with exce66 hydrazine monohydr~te in ~ethanol a~ reflux for 6everal hours. Under cer-tain conditions 6ulfonamide6, ~I, may ring-clo~e ~o sacc~arin-like 6tructure~, ei~her during their prepa-ration in Reaction 5(a) or ~uring reflux with hydra-zine in ~eaction 5(b). In either case, sub~equen~
reac~ion with hydrazine as de6cribed above may pcovide hydrazide~, XII.

.~5~

17 eaction 5~L
The conver6ion of ~ydrazlde~ to 5-~ercapto-oxadia201e~ ia well-known in the liteLature, e.g., R. W. Young and K. H. Wood, J. Am. Chem. Soc., 77~ 400 ~1955). In a typical procedu~0, hydrazide~, ~II, are heated at ~eflux with equimolar amount6 of potas6ium hydroxide and an exce~ of carbon di~ul~ide in methanol or ethanol ~olvent until the evolution of hydrogen ~ulfide has nsarly ~topped. Oxadiazole6, IIIb ~R5=H), are isolated by concent~ation oP the ~olvent, addition of water to the re~idue, filtration of the aqueou6 6u6pen~ion to remove in~oluble impuri-tie6, acidificatio~ of the aqueou~ filtrate with hydrochloric acid and filtration.
Alkylation of 5-mercaptoo~adiazvles i~ al~o well-known in the literature, e.g., S. Giri et al., Aqr. Biol._Chem., 40, 17 (1976). Typically, oxadi-azole~, IIlb (R5=H), are reacted with an equimolar amount of base , e.g. pota~sium hydroxide and exces~
alkylating agent, R5M, at reflux in an inert ~olvent e.g. methanol or ethanol for 0.5 to 24 hours.
Sulfonamides, IlIb, are i~olated by concen~ration of the ~olvent, addition of water to the re&idue and fil~ration. Fo~ the ca6e where R5=CF2H, the reaction 25 i8 p~eferably run in DMF ~olvent at 60-90C with exce6~ pota~ ium carbonate as ba~e. Following addi-tion of water, ~ulfonamides, IIIb, are isolated by filtration.
2- and 3-~yridine6ulfona~ide6 of Formula XII, ~ub~tituted in the 3- and 2-po6ition~ respec~fully wi~h a p~enyl group, may be prepared from corre-6ponding 3-phenyl-2-pyridinol~ and 2-p~enyl-3-pyridinol6, ~III, by the ~equen~e of reactio~ ~hown below in ~qua~ion 6.

1~1 ~ .
~(a~
OH S ~H

Rl ~ ~ > ~ ~ ~ Rl (iii) base IV

SO NH
(i) C12, HCl, ~ 2 2 XIV C12, X~F R
~ J
(ii) NH~OH; ' ` N~
or NH3 IIIc wherein Rl is as previously defined.

ReactiQn 6~2 In theQe reactions mercaptopyridine~, ~IV, are prepared by analogy with the tea~hing6 of B. Blank et al., J. Med Chem., 17, 1065 (1974). The method com-prizes (i) reacting pyridinol6. ~III, with dimethyl-thiocarbamoyl chloride and a base, e.g. 1,4-diaza-bicy~lo[2.2.2]octane tDABCO) in D~F to form the ~orre-6ponding N,N-dime~hyl-O-thiocarbamate6: sii) hea~ing ths6e compound~ at elevated eemperature~ e.g., 1~0-210~C to form the corre~ponding N,N-dimethyl-S-carbamates; and (iii) heating the~e compound~ with a ba6e , e.g. ~odium carbonate or 60dium hydroxide in an inert 601vent, e.g. methanol to form ~ercapto-py~idine6, ~IV.
Reaction 6~k~
These reaction~ are run by procedurs~ analogou~
to tho~e de~ribed ~bove for the preparation 3f ~I
(Equation sa).

2- and 3-Pyridinesulfonamid~3 of For~ula III, 6ub6tituted in t~e 3- and 2-po6ition6 re6pe~tively with pyridinyl, py~imidinyl, pyrazinyl. pyridazinyl or triazinyl group~ Q-27 to Q-3fi) may be prepared by the sequence of reaction~ shown in Equation 7 below.
Equ~t~on 7 7(a~
~r Li 10 Rl ~ S~2~HC(CH3)3 - L ~ Rl ~ S02NC(C~3)3 N N Li ~V XV I

7(b~ Q
XVI 1) CuI ~1 ~ S02NHC(CH3)3 ~VII
~VIII

20 7(c) Q
~VIII CF3CO?H Rl ~ S2NH2 IIId wherein Rl ifi H or CH3; and Q i~ ~-27 to ~-36.

T~e ~ompound~ of Formula III(d) are prepared by analogy with ~he teaching6 of EP-A No. 85,476 ~publi~hed December 13, 1983).
Reaction 7~a,b) An appropriate 2-bro~o-3-(N-~-bu~yl)pyridine-~ulfonamide or 3-bromo-2-(N-t-butyl)pyridi~e~ulfon-amide i6 dis~olvad in an ethereal 601vent, e~g~

,,~ r"~ )r.-~

te~rahyd~o~u~an, and two equivalent~ o~ n-butyllithiu~
ln hexanes are added at about ~70~C. After 1-5 hours at about -70C, the corre6ponding co~pound of Formula ~VI is formed. This is not i601ated. but one equiva-lent of copper(I) iodide i6 added at about -70C, followed by 1-1.5 equivalents of an appropriately substitu~ed heteroaromatic iodide of Formula XVII.
The reaction mixture i8 stirred at 0 to 70C for 1 3 day~, concentrated and poured onto aqueou~ ammonia.
Co~pounds of Formula ~VIIX are isolatad by filtration i~ solid~, or by extraction with methylene ehloride and concentration i~ oil~" The compound6, XVIII, may be further purified by recry6tallization or chromato-graphy procedures. The compounds of Formula XV and ~VII may be prepared by methods known to those skilled in the art. Pertinent references for the peeparation of iodocompounds, XVII, are described in EP-A No.
85,476.
Reaction 7(c~
This reaction is conducted by ~tirring a compound of Formula ~VIII with 2-10 equivalents of ~rifluoroacetic acid or aqueou~ HBr wath or without an inert solvent at 30-70C for 1-3 day~. The product, IIId, may be i~ola~ed as a trifluoroaceta~e or hydro-bromide salt by evapo~ation of solvent and excess acid and trituration with ether. The free base may be obtained by neutralization of the salt with aqueous base, extraction into an organic solvent, and concen-tration of ~h~ organi~ e~tract~.
2- and 3-Pyridine6ul0na~ide6 of For~ula IIIe can be prepared as ~hown in Equation 8 by procedures analogou~ to the preparation of Co~pounds IIIb described in Equation 5.

Rl~CH3 _-BuLi ~R ~ 2Li N SO2NHC(CH3)3 L N SO2NLiC(CH3~3J
XXVI I T XVIa 2 TFA ~ ~C~Iz;C02H

~XI~

N-N
1. CH3OH~H2SO4 CEI~O~SP~"
2. NH2NH2oH?O Rl~ 2 5 3. KOH/CS2/H20 ~ S2NH2 4 . KOH, R 5M
IIIe 20wherein Rl is as previously defined;
R5 is Cl-C3 alkyl or CF2H; and . M is Cl, E~r or I .

Compounds of Formula I I If in Equation 9a can be prepared from ehe lithium salt I~VIa by procedure~
described for the p~eparation of similar compounds in Equation 7 and Compound IIIg can be prepared as shown in Equation 9b.

t~ r, ~~

~./Ia ~ ~ C~2-Q
~ 502NE~C ~ CH3 ) 3 TF~ _3, l~ CH2-Q

wherein Rl is H; and Q i~ Q-27 ~ Q-36.

Equa~ion 9b 21~ Rl~/~

2 ~ TFA S2~2 l'he dilithio ~alt ~VIa call be prepared by 25 li~chia~cion o the ~ppropriate picollneRulfonamide6 a~cording to the teachi~g8 o~ R. E. Smitht S. Boatman and C. R. Hauser; J. Or~, 33, 2083 (1968).

2~ieropy~idi~e6 o~ Fo~mula ,~h ~on~aini~ an 30 o-alkylfuran or ~hiophelle group (Q is Q-22 to Q-25 3, can be prepared by analogy with the teachings in EP-P~
No. 85,476, and referen~es clted thereill as illustrat~d in Equatioll lO.

r~ r ~
~3 E.quation lQ
(CH~)n-I ( 2)n Q
R~ CU~
N No2 ~X~I N N02 X~ IIIh wherein Rl and n are a~ originally de~ined; and Q is ~-22 ~o Q-25.

Thus, a furyl- or thienylcopper compound of Formula ~I is ~eacted witlh an o-(iodoalkyl)nitro-pyridine of For~ula ~ in ,an in~rt 801vent,~e.g.
pyridine or guinollne at 0 to 60C for 1-3 day~. The product, IIIh, i8 i~olated by addition of acid , e.g.
aceti~ acid and water, axtraction ~ith methylene chloride, stripping of ~olvent and chromatog~aphing the crude product. The ~opper compound~ of Formula ~XI are prepared by reacting the corresponding lithium compounds with cuprou~ iodide or cuproufi bromide in an inert ~olvent e.g. : ~thyl ether. The detailed procedure~ for analogous type~ of reaction~
are de6cribed in the following re~erence6: ~. Nil~on and C. Ulleniu~, A~ta. Che~m. Scand., 24, 2379-2388 (1970); C. Ulleniu6, Acta. Che~. Scand., 26, 3383-3386 (1972).
2- and 3-Pyridine~ulfonamides of Formula III
~ubsti~uted in the 3- and 2 posi~ion~, re6pectively, with a tet~ahydrofuran group (Q iB Q-26) may be pre-pared a~ shown in Equation 11.

t, ~ Hz ) n~
S02NHC(CH3)3 ~I~

ll(b) I~ CF3CO~H Rl ~ (CH2~ o IIIe whecein Rl is H or CH3; and n i6 0 or 1.

The compound~ of Formula IIIe are peepa~ed by analogy with the teaching~ in EP-A No. 85,476 (published August 10, 19833.
Reaction ll(a~
In thi6 reaction d~lithio salt, ~YI or ~VIa, in tatra~yd~ofu~an is treated wit~ one equi~alent of 4-chloro- or 4-bcomobutyraldehyde at -70C to -80C.
25. ~fteE ~tirring a~ about 25C for 1-3 days, ~e c~ac-tion i~ quenc~ed by the addition of an acid e.g.
ace~i~ acid, and the product, ~ i601ated and purifi~d by ~tripping t~e ~olvent and ~hromato~raphing the residue.
eaction_llrb~
Thi~ reaction i6 run by proceduces analogous to tho~e de~ccibed above in Eguation 7(~).

3 Py~idine~ulfonamide6 of Formula lIIi. ~ubsti-tuted in the 2-pvsition by a furan or ~chiophene group (Q is ~ 22 to Q-25 ) ~oay be prepar*d a~ ~hown below in Equatlon 12.
5 E~uation l?
2(a) R7 P~l~(N2 , ~ R:I~No2 N Cl ~Br ) N Q
~XI
XX X~ I I

12(b) XXI I ~ i ) Reduction R ~ S~NH2 ( ii ) MEERWEIN '' ~ ~
(iii) NH3 o~ NH40~1 N Q
IIIi wherein R~ 5, R6 and R7 a~e a~ originally defined;
Q i6 Q-2~ to Q-25: and N il; 0 or S.

Reaction~ 12 (a, b2 In Reaction 12~a) a furyl- or thienylcopper com-pound of Formula XXI i8 reacted with an appropria~e chloro- or bromonitropyridine of Formula ~ in a ~ol-vent , e.g. pyridine or quinoline. The copper com-pounds of Formula ~I are prepared by ~eacting the ~orre~ponding li~hium compound~ with cuprou~ iodide or cuprous bromide in a solvent , e.g. diethyl ether.
T~e detailed procedure~ for analogous ~ype~ of reac-tion6 ar~ de6cribed in the following referen~e~:
M. Nil6~0n ~nd C. Ulleniu6, cta. Chem. Scand., 24, 2379-238~ (19703; C. Ullenius, Acta. Chem. Scand., 2S.
3383-33B6 (19723.

2-Pyridine~ulona~ide~ of Fo~mula IIIj, substi-tuted in the 3-position by a furan or thiophene group (Q iB Q-22 to ~-25) may be prepared by the sequence of reaction6 ~hown in Equation 13 below.
5 Equation 13 13(a) ~7 R6 Rl ~ Cl(R~ V > 1 ~ Cl(R~) XXIII X~V

13(b) X~V KSR14 ~X

XXVI
13(c) XXVI (. ). C12~ H20, CH3C02H ~ Q
(ii~ NH40H ~ N'l~S02NH2 wherein Rl, R5, R~ and R7 are a~ originally defined;
1~ i6 CH2CH~CH3 o~ CH2C~H5;
Q i~ Q-22 to Q-Z5; and i6 0 or S.

J~ `r~ ~

Reactlon 13fa~
-In thi~ reaction a 2-halo-3 pyridyl diazonium 6ale i~ ~oupled with an appropeiately 6ubstituted thiophene or furan in the presence of a cataly6t, e.g.
cupric chloride. This reaction may be r~n by procedure6 analogous to tho&e de~ceibed ln Gomberg and Bachman, J. Am. Chem. Soc.. 46, 2339 (1924); J. John-fion, J. Ch _. Soc., 895 ~1946); and in 3. Pharm. Soc.
(Japan), 90, 1150-1155 ~1970), or simple modifications ~0 theceof, by those skilled in the art. In ca~eE where both the a- and the B-po~ition of the thiophene or furan are available for couplinq, both i~ome~s are usually obtained with the la-coupled product being ~he predominant isomer. These i~omers may be 6epa-rated by fractional ~rystallization or chromatography procedure6.Reaction 13~b3 I~ thi~ reaction thiopyridine~ of Fo~ula ~VI
are prepared by conventional method6 by treating 2-halopyridine6. XXV, ~ith potas6ium benzyl or propyl-mercaptan in an inert 601ven~ e.g. DMF at abou~ 25 to 130C for one to 24 hours. ~ollowing i~olation by u~ual method~, the product, X~VI, may be purified by chromatography p~o~edures.
_eaction l~Lc3 And in ~his reaction the product~ of Reac~ion 13(b) are oxidatively chlorinated in a ~uitable inert ~olvent, e.g. chloro~orm, methylene chloride or acetic acid, in the presence of water, to pLoduce the cocrefiponding sulfonyl chloride~. The reaction i8 carried out in the pre~ence of at lea~t 2.5 molar equivalent~ of water and at least three molar equiva-lent~ of chlorine at about -30 eo 5C for l-S hours.
~ollowing isolation of the 6ulfonyl chlo~ide~, the sul~oRyl chloride~ a~e reacted with ammonia or ammonium hyd~oxide by conventional methods.

j~ "~"

Other 2- and 3-pyridinesulfonamide~ of Fo~mula III may also be prepared by oxidatively chlorinating appropriate 3-heterocyclic-2-thiopyridines and 2-heterocyclic-3-thiopyridine6 of Foemula ~VII to coree~ponding sulfonyl chlorides, followed by amination to corresponding 6ulfonamides, a~ shown below in Equation 14.
Equation 14 Xl ~ SR (i) C12, H20, inert fiolvent IIIk N ~ (ii) NH3 or NH40H
XXVII
wherein Rl i6 as originally defined; and R15 is H- C2Hs or CH2 6 5 The r~actions of Equation 14 are carried out by methods analogous to those described above in Equation 13(c) and for the preparation of XI (Eguation 5a~. The compounds of Formula XXVII may be prepared by those skilled in the art by the application of appropriate ~ethod~ ~elected from the va~iety of known literature procedures for preparing ~ubstituted aromatic hetero-cycles. See, for example, ~P-A No. 83,975 Ipubli6hed July 20, 1983) t a~d references cited therein, which desccibe method~ for tran~focming various o-(substi-tuted)nitrobenzene~ to corresponding o-(he~erocyclic)-nitrobenzenes, in which the o-heterocyclic groups are Q~l to Q-Zl. By carrying out similar reactions on appropriately ~ubstituted pyridine~, or simple modifi-cations thereof, tho6e ~killed in the art may prepare many of the compound~ of For~ula XXVII above.

r~" ~ o~ i r~

The~e exist ~ va~lety of kno~wn ~ethod~ fo~
incorporating a ~ercapto oc alkylthio group into the 2- or 3~po~ition of a pyrldine ring, ~ethods which ace u6eful for the preparation of the compound6 of the general Formula ~VlI de6cribed above in Equation 14.
The choice of met~od6 used depends in part on the reaction 6equences u~ed to prepare compounds X~VII, which would be obviou~ to tho~e ~killed in the art.
These method~ include (i) reactin~ 3-pyridyl diazonium lQ 6alts with potas~ium ethyl xanthat~ to for~ corre-~ponding 3-~ercaptopyridine6, which can be alkylated to 3-benzyl- or 3-pcopylthiopyridines by obviou6 method6; for details, refer to analogous reactions described in J. Pha~m. Belq., 22, 213 (1967); ibid., 29, 2Bl (1974) and J. Orq. Chem., 23, 1924 tl958);
(ii) ~aponifying N,N-dimethyl-S-carbamates, prepared from 2- or 3-pyridinols, to form co~responding 2- or 3-mercaptopyridines: for general detail~ ~ee Eguation 6(a) above; (iii) reac~ing 3-halopyridines, containing an ac~ivating ortho-group su~h a6 aldehyde, ketone, carboxylic ester, amide, nitrile or nitro group, wit~
potazsium propanethiol or benzylthiol in an inert ~olvent, e.g. DMF or hexamethylphosphoramide by ~nown method~ to for~ co~esponding 3-benzylthiol- or 3-propanethiolpyridine6; (iv) di~placing a 2-halogen on a pyridine ring by ~ulfu~ nucleophile6, e.g.
potas~ium o~ 60dium hydro~ul~ide, thiourea or po~as-sium benzylthiol or propanethiol to form 2-thio~ub-6ti~uted pyridines; for detail~, see analogou~
reaction~ described in J. Het. Chem., 3, 27 (1966);
ibid., 17, 149 (1980), ibid., 5, 6~7 ~1958); J. Am.
~hem. Soc., 6B, 342 (1946) and ibid., 70, 3908 [194B);
and (v) diazotizing and converting Z-aminopyridine~ to 2-pyridinols which may be converted to 2-pyridin~-thiol~ with P4S~; ~or detail6 6ee analogous ~eactionsde~cribed in ar~aco Edo Sçi~ 22~ 1069 (1967)~

f~ J~

The preparation oP pyridine~thiol~ i8 alBO
reviewed in "Pyridine ænd It~ Deriv~tives", Part 4, 1964, by ~. L. Hale, a part of the ~erie~ "The Chemi~tr~ o~ HeterocYclic Com~ , A. ~ei~berger, Ed., publiEhed by Interfi~ience Publ., Ne~ York and London.
The heterocyclic amine6 of Formula YII in Equation 3 are also important in~ermediate~ for the preparation of t~e compound~ of this invention, and ~an be prepared by ~e~hod~; known in the literature, or 6imple modification~ thereof, by eho~e ~killed in the art. For detailç, see, for example, EP-A No. B4, 224 (publi~hed July 27, 1983) and W. Braker et al., J. Am.
Chem. Soc., 69, 3072 [1947), which describe the 6yn-ttlesi~ of pyrimidine- and triazineamines ~ubstituted by acetals and thioacetals, e.g. dialkoxyme~hyl or 1,3-dioxolan-2-yl. See al~o, for example, South African Patent Application Nos. 825,045 and 825,671 which de6cribe the ~ynthesi~ of aminopyrimidines and triazi~e~ ~ub6tituted by such group~ as haloalkoxy or haloalkylthio group~, e.g., OCH~CH2F, OCHzCF3~ OCF2H
or SCF2H. Al~o, South African Patent Application No.
S37~434 (published October 5, 1983~ de~cribes ~ethod~
for the 6ynthe~i~ of cyclopropylpyrimidines and tri-azines 6ubstituted by ~uch groups as alkyl, haloalkyl,alkoxy, haloalkoxy, alkylamino, dialkylamino or alkoxyalkyl.
Al~o, the 5,6-dihydrofuro[~,3-d]pyrimidin-2-amine6, the cyclopenta~d]pyrimidin-2-amines (VII.
A=A-2) and the ~.7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-amine6 (VII, A=A-3) ~an be prepared as de~cYibed in EP~A No. 15,683. Also, the furo[2,3-d~pyrimidin-2-amines (VII, A-A-4) are de~cribed in EP-A ~o. 460677.
Compounds of Formula VII, where A is A-5, are de~ribed in EP-A No. 73,562. Compounds of Formula YII, whe,ce ~ i5 A-6, are de~cribed in EP-A No. 94,250.

ln addition, general methodE~ Por preparin~
aminopyrimidine~ and t~iaz~nes have been reviewed in the following ~ublication~:
~ "The Chemistry of Heterocyclic Compounds", a secie~ published by Interscience Publisher6, Inc., NQW
Yor~ and London:
o "Pyrimidines", Vol. 16 of the sa~e series, by D. J. BLown.
~ "s-Triazines and Derivative6", Vol. 13 of the 6a~e series, by E. M. Smolin and L. RappapoLt; and ~ F. C. Schaefer, U.S. 3,154,547 and K. R.
Huffman and F. C. Schaefer~ J. Orq. Chem., 23, lB12 (1963) wh;ch describe the ~ynthe~i6 of triazines.
Agriculturally suitable salts of compounds of Formulae I and II are al60 useful herbicide6 and can be prepared in a number of way6 known ~o the art. For example. meeal ~al~s can be made by contacting com-pounds of Formulae I or II with a ~olution of an alkali or alkaline earth metal salt having a suffi-ciently ba~ic anion (e.g., hydroxide, alkoxide,cacbonate or hydroxide). Quaternary amine ~alt~
can be made by similar techniques.
Salts of compounds of Formulae I and II can al60 be prepared by exchange of one cation for another.
Cationic exchange can be effected by direct contact of an aqueous solution of a salt of a compound o For-mulae I o~ II (e.g., alkali or guaternary amine ~lt) wi~h a solution containing the cation to be exchan~ed.
Thi~ me~hod i~ most effeceiYe when the desired 6alt con~aining the exchanged cation i~ in~oluble in water and can be separated by filtration.
Exchange may also b~ effected by pas~ing an aqueou~ ~olution of a 6alt of a compound of Formulae I
or II ~a.g., an alkali metal or quaternary a~ine 6alt) through a column packed with a cation exchange re~in ,,~ r ~ ,2~ r~J, 3 !
containing the cation to be exchanged ~OL that o~ the original ~alt and the de~ired product i8 eluted fro~
the column. This method i~ particularly useful when the de6ired salt ~ 6 water-~oluble, e.g., a pota~ium, sodium or calcium salt.
Acid addition ~alt6, u~eful in this invention, can be obtained by reacting a compound of Focmulae I
or II with a sui~able acid, e.g., p-toluene~ulfonic acid, trichloroacstic acid o~ the li~e.
' The preparation of t'he compound6 of ~his invention i6 further illu~trated by the following specific examples. Unle~ otherwise indicated, ~emperatures are in degree6 centigrade.

ExamPle 1 Nitro-2-(lH-1.2,,4~triaz 1-l_y~2pyridine A solution of 10 g of 2-chloro-3-nitropy~idine di~solved in 30 ml of dry D~' was added dropwise to a 6u~pension containin~ 6.9 g of 1,2,4-triazole 60dium ~alt (90~, Aldri~h Chemical Co.) in 40 ml of dry DMF.
After a Elow exotherm had subsided, the 6u~pension was heated at 60 for three hours, then cooled to 25C and poured onto S00 ml of ice-watel to yield a precipitate.
After the mixture was filtered, the isolated 601id was ~5 wa~hed 2x50 ml of water and ~uction-dried to yield 12 g of crude produc~. The product was recry~tallized from 2-propanol to yield 8 g of the ~ubject compound;
m.p. 131-133~.
Anal. calc. for C7H5N502: C, 43.9; H, 2.7; N, 36.6;
Found: C, 44.6: ~, 2.7; N, 36.7.

ExamPle 2 3-Amino-2-(lH-1.2,4-tr~azol-1-y~p~ridine To ~ suspension containing 35.4 g of stannoug chloride dihydrate in 100 ml of concentlated hydro-S chloric acid wa~ added portionwi~e 10 g of the com-pound prepared in Example 1 over a 0.25 hou~ period.
After the re~ulting exotherm (23-79) slowed, the 6u~pension was heated at 85-90 ~o~ one hour, then cooled to 0. The mixture was poured onto excess ice-water (about 700 ml), and the su~pen~ion wa6 made st~ongly basic to litmus by addition of 50~ aqueou6 NaOH to yield a precipitate. After filtering the mixture, the isolated 601id was washed with water, suction-dried, then recry6tallized ~rom ethyl ace-tate-hexanes to yield 3 g of the 6ubject compound;
m.p. 103-105~.
Anal. calc. for C7H7N5: C, 52.2; H, 4.4; N. 43.4;
Found: C, 52.4; H, ~.3; N, 41.6.

~o Exam~le 3 2-(lH-1,2,4-Triazol-1 yl2-3-pvridinesulfonyl chloride A diazonium salt was p~epared by adding a ~olu-tion o 9 g of ~odium nitrite in 30 ml of water to a suspen6ion of 20 g of the compound prepared by the procedure of Example 2 in 45 ~1 of concentrated hydro-chloric acid and 127 ml of glacial acetic acid at 0-25. After stirring about 0.4 hour, ~he diazonium ru~pen~ion was poured slowly into a mixtu~e con~i~ting of 93 ml of aceti~ acid, ~.3 g of cupric chlolide dihydrate and 37 ml of 6ulfur dioxide while cooling the reaction flask at 10-20 in a dry ice-acetone bath. During the addi~ion a delayed vigo~ous gas evolution with foal~ing occurred and was controlled by cooling and decreasing the rate of addition of the diazonium ~uspen6ion. After addition was comple~e, $;~7J..')~

the cooling was csmoved and the 6u~pension was ~tirred at ambient temperature for four houc6. The su6pension wa~ pou~ed into ice-water (about 800 ~1) and stirred ~o yield a solid. After the ~ixture wa~ filtersd, the i~olated 601id wa6 wa~hed 2x50 ml of water and suction-dried overnight to yield 17 g of the sub3ect compound:
m.p. 12B-132~
Anal. calc. for C7H5ClN~02S: C, 34.4; H, 2.1; N, 22.g;
Found: C, 34.4: H, 2.1; N, 23.2.
Exclmple 4 2-(lH-l,Z,4-Tliazol-l-Yl~-3-Pyri-din~Qg~ a~
To a suspension containing 15 g of the compound pLepared in Example 3 in 125 ml of tetrahydrofuran was added dropwise 23 ml of concen~rated aqueous ammonium hydroxide while maintaini~g the reaction te~peratu~e at 10-20 with external ice-water cooling. After stirrin~ at room tempecature for three hours, the suspen~.ion was concentrated in vacuo to a water su~pension. The suspension waF. poured into ice-water (about 200 ml) and stir~ed to yield a solid. The mixture wa~. filtered to yield 12 g of crude product, which was recry6tallized from acetonitrile to yield 8 g of the subjec~ compound; m.p. 185-188~.
Anal. calc. for C7H7N502S: C, 37.3; H, 3.2; N, 31.0;
Found: C, 37.4, H, 3.0; N, 30.9.

Example 5 N-[~4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2~ 1,2,4-triazol-1-Yl)-3-Pyridine~ulfonamide To a su~pen~ion containing 0.5 g of the ~ulfon-amide prepared in Example 4 in 10 ml of p-dioxane wa~
added 0.6 g of phenyl(4,6-dimethoxypyrimidin-2-yl)-carbamate followed by 0.33 g of l,~-diazabicyclo-[5.4.0]undec-7~ene ~DBU). The ~u6pen~ion wa~ stirred ~fqr~ "~?)5;

at room temperature fo~ about two hours then diluted with about 75 ml of water to for~ a ~olution. Afte~
acidifying the 801ution with conc. hydrochloric acid (red to litmus) and 6tirri.ng 0.5 hour, a precipitate formed. The mixture wa~ filtered and the i601at,ed ~olid wa~ wa6hed with 10 ml water and suction-dried for 24 hour~ to ~ield 0.7 g of the 6ubject compound:
m.p. 226-Z30.
Anal. calc. for C14H14N805S: C, 41.4; H, 3.5: N, 27.6;
Found: C, 41.3; H, 3.7; N, Z7.~.
IR (nujol): 1715 cm-l (C=O).

U~ing the techniques described in Equations 1-14 and Examples 1-5, or ~imple modifications thereof, the following compounds in Tables Ia-IIg can be made by tho~e skilled in ~he art.

T~ble Ia ~1 ~ R ~

O n R aI X Y Z m p.C
Q-l(R5,R6=H) 0 CH3 H OCH3 OCH3 CH
Q-l(R5,R6=H) 0 HH CH 3 ~H3 CH
Q-l(R5,R6_H) 0 HH CH3 OCH3 CH
Q ( 5'R6 H) HH OCH3 OCH3 CH
Q-l~R5,R~=H) 0 HH Cl OCH3 C~l Q-l(R5=H,R6= CH3) 0 H H OCH3 OCH3 CH
Q (R5 CH3'~6 H) o H H OCH3 OCH3 CH
Q-2 (R5 'R6=H) 0 HH CH3 CH3 CH
Q-2(R5,R6=H) 0 HH OCH3 OCH3 CH
20 Q ( 5~ 6 ) HH CH3 OC~3 CH
Q-2(R5,R6=H) 0 HH Cl O~H3 CH
Q-2(R5=CH3,R6=H) 0 HH OCH3 OCH3 CH
Q-2(R5=~,R6=~H3) 0 HH OCH3 OCH3 CH
Q-3(R5.R6=H) 0 HH CH3 ~3 CH
Q-3(~5,R6=H) 0 HH CH3 OC~3 CH
Q (R5,Rh H) 0 HH OCH3 OCH3 CH
Q-3(R5,a6=H~ 0 HH Cl O~H3 CH
Q-3(R5=CH3:~=H) 0 H H OCH3 OCH3 CH
Q ( 5'R6 H~ 0 HH CH3 CH3 CH
30 Q ~ 5' 6 H~ o HH OCH3 CH3 ~
Q-4(R5.R6=H) 0 HH OCH3 OCH3 CH
Q-4(R5.R6=H) 0 HH Cl OC~3 CH
~-5rR5'R6=H) 0 HH OCH3 OCH3 CH
Q-5(R5.RS=H) O H3 CH3 CH
Q-5(R5.R6=H) 0 HH CH3 ~C~3 C~
Q-5~R5'R6=H~ 0 HH Cl OCH3 CH

~Ea~ /~A~ d ~ y ;!~ C
4~chloropherlyl O H OCH3 OC:H3 CH
3-alsthoxypbenyl O H H OCH3 OCH3 C~
3-D~ethylphenyl O H H OCH3 OCH3 CH
Q-6 (E~5-H) O H OCEI3 OC~13 CEI
Q~ 6 ( R5 ~H ) O H H C}13 OC~3 CH
Q-6 (~5~H) O H CE~3 C}s3 CH
Q~ 5~) H Cl ~3 CH
Q-7(R5~R~ 7-H) O E~ C~3 C~H3 CH
Q-7(R5~R6~R73~I) O H OCH3 OCH3 C~I
Q-7(R5,E16~R7-H) O H H CH3 OCH3 C~
Q-7 (P~5, R6 ~ El7-H) O H H Cl OCH3 CH
Q-7(L~5,~71~CH3 ~6~H) O H H OCE13 OCH3 CH 204~207 Q-0 (R5 ' ~H) O E~ El CH3 CH3 CH
Q-E~ (R5 ~ 2H~ O H E~ OCH3 OCH3 CH
Q-8 (R5 ~ -H) O H H CH3 OC~3 CH
Q-B tR5 ' =H) O H H Cl OCH3 CH
~;!-B (R5 ' =CH3 ) O lH H OCH3 OCH3 CH
Q-8 (R5 ' =CH3 ) O EI H CH3 O(:H3 CH
Q ~ ( R5 H3 ) H H CH3 ~H3 CH
Q-8 (R5 ' ~CH3 ) O H H Cl OCE13 CH
2 5 Q ( 5 3 ) O CEI3 H OCH3 OCH3 ClH
Q-8 (P~ ' ~C lH ) O H H CH3 c~3 CEI
Q 8 (R5 C2E~5 ~ O H H OCE13 OClH3 C~H
Q-8 (R ' ~C H ) O H ~I CH3 OCH3 ~H
Q-- 8 ( ~5 ~ ~cC2H5 ~ O ~ l OCH?~
Q-8 (R5 ~ SCH3 ~ O E~ H OCH3 OCH3 CEI
Q (R5 SCH3 ) O H 1H CH3 C~3 CH
Q-8 (R5 ~ 8S~E~3 ) O H 3 CH3 CH
Q-8 SP~5 ~ -SCH3 ) O H H Cl OCH3 CH
Q-~ 5 ~SC2H5 ) O H 3 3 CH
Q- 8 ( R~ SC2H5 ) O El H OCE~3 OCH3 CH
Q ( 5 2 5 ) t) H H CH3 5:~CH3 CH

'1~ /'3~ .q~
3~
~ gLlg-c~æ~ ued _Q_n R Rl ~ y Z m.p.oC
Q-8(R5'=SC2~5) H H Cl OCH3 CH
Q-8(R~'=SCH2CH3CH2) O H H OCH3 OCH3 CH
Q-8(R5'=SCH2CH=CH2) O H H CH3 OCH3 CH
Q-8(R5'=SCH2CH=CH2) O H H CH3 CH3 CH
Q-8(R5'=SCH~CH=CH2) O H H Cl H3 CN
Q-8(R5'aSCF2H)CH3 OCH3 CH
10 Q-8(R '=SCF H)O H H CH3 CH3 CH
Q-~(R5'=SCF2H)o H H OCH3 CH3 CH
~-h(R5'=~C~2H)O H H Cl OCH3 CH
Q-8~R5'=SC3~7)H3 OCH3 CH
15 Q (R5 SC3H7)~H3 OCH3 C~
Q-8(R5'=SC3H7)O H H Cl OCH3 C~
Q-8(R5'-OCH3)o H H OCH3 OCH3 CH
Q-8(R5'=OC2~5)H3 OCH3 CH
Q-9(R5=H)O H H OCH3 OCH~ CH
Q-9(R5=H)O H H CH3 OCH3 CH
Q-9(R5=H)O H H CH3 CH3 CH
Q-9(R5=H)O H H Cl OC~3 CH
Q-9(~5=CH3)O H H OCH3 OCH3 CH
Q (R5 CH3)O H H CH3 OCH3 CH
Q-9(R5=CH3)O H H CH3 CH3 CH
Q-9(R5=CH3)O H H Cl OCH3 ~H
Q-lO(R5=H)O H H CH3 CH3 CH
Q-lO(R5=H~H3 OCN3 CH
Q-lO(R5=H)CH3 OCH3 CH
Q-lO~R5=HO H H Cl OCH3 CH
Q-10-(R5=CH3)o H R CH3 CH3 CH
Q-10-(R5=CH3)O H H OCH3 OCH3 CH
Q-10-(R5=CH3)O H H CH3 OCH3 CH
Q-10-(R5-CH3~o H H Cl OCH3 CH

Q-ll(R5=H)O H H OCH3 OCH3 CH
Q-12(R~='H3O H H OCH3 OCH3 OEl 3~

~able Ia Continued Qn lR Rl ~ Y Z P.C
2(R8=cl)OCH3 OCH3 CH
Q-13~R5-CH3)1 ~ O~H3 OCH3 CH
Q-14(R5=H) 3 3 Q-14(R5=EI)3 CH3 C~
Q-l~(R5=H)0 H H Cl OC~3 CH
Q-15(~5=H)l~ H OCH3 OCH3 CH
Q 16(R5,R6 H) 0 H H CH3CH3 CH 240-243 Q-16(R5,R~=H) 0 IR H OCH3 OCH3 CH 235-23B
Q-16(R5,RS=H) O 'H H CH3OCH3 CH 225-228 Q-16(R5,R6=H) 0 H H ClOCH3 CH
Q-17(R5=CH3.R6=CH3) H H OCH3 OCH3 CH
Q-17(R5=CH3,R6=CH3) H H CH3 OCH3 CH
Q-17(R5=H,R6=CH3) 3 CH3 CH
Q-17~R5=H,R6=CH3) 0 H H Cl OCH3 CH
Q-l8~R5=H~R6=cH3~ 3 3 Q-18(R5=CH3oR6=cH3) 3 3 Q-lB(~5=H~R6=CH3) 33 CH
Q-18(R5=H,R~=CH3) O H H Cl OCH3 CH
Q-l9(R5=CH3,R6=H) H3 OCH3 CH
Q-20~R5,Rfi=CH3) H H OCH3 OC~3 CH
Q-21(~5~6~R7=H) 3 C~3 C~
~-22(R5,R6,R7=H3 H H OCH3 OCH3 ~H
Q-23(a5~R6~R7=H) 3 CH3 CH
Q-~4~R5~6.~7 )O H H O~H3 CH3 CH
Q-25(R5,R6,R7=H)H H ~CH3 OCH3 CH
Q-26(W'=O~ 3 3 CH
Q-27(R5.R6=H~n'=) 3 3 Q-28(R5~R~-H~n~=o) 3 3 Q-29~R5,R6=H,n'=O) o H H OCH~ OCH3 CH
Q-30(R5=H;Rg~Rlo=OCH3) 0 H H OCH3 OCH3 CH
Q-30(R5=H Rg~Rlo=CH3) 0 H H OCH3 OCH3 CH
Q-31(Rg,RlOaH) o H ~1 OCH3 OC~3 CH

~9 Table Ia Continued ~ n R ~1 ~ Y ~ P.~
5 Q 32 (R9 ~Rlo H) o H H OCH3 OCH3 CH
Q-33(R5,R6=H) O H H OCH3 OCH3 CH
Q 34(~5'R6 ~) O H H OCH3 OCH3 CH
Q ( 11~ 12 3) H H OCH3 OCH3 CH
Q 6(Rl1~R12 CH3) O H H OCH3 OCH3 CH

C6~I5 O H H OCH3 OCH3 CH
C6H5 0 H EI Cl OCH3 CH
Q-l(R5,R6=H) o H H CH3 OCH3 N
15 Q 2(R5~R6 H) O H H OCH3 OCH3 N
Q-3(~5=CH3,R6=H) O H H OCH3 OCH3 N
Q-8(R5'-CH3) o H H CH3 OCH3 N
Q-8(R~'=SCH3) O H H OCH3 OCH3 N
~ ( 5 3) O H H CH3 OCH3 N
Q-lO(R5=CH3) O H H CE13 OCH3 N
Q-12(R8-Cl) O H H CH3 OCH3 N
Q-17(R5=H,R~=CH3) O H H OCH3 ~H3 ~-18(R5-H,R6=CH3) o H H CH3 OCH3 N
Q-18(R5=H,R~=CH3) O ~ H OCH3 OCH3 N
25 Q 2(R5~6,R7 H) O H H CH3 OCH3 N
Q-26(~'=0~ O H H CH3 OCH3 N
Q-27(R5,R6=H,n-~-O) O H H CH3 OCH3 N
Q-27~R5,Rs=H,n~=O) O H H OCH3 OCH3 N
Q-30(R5~Rg~Rlo=H) O H H CH3 OCH3 Q-30(R5~Rg~Rlo=H) O H H OCH3 OCH3 N
Q-33~5'R6=H~ O H H CH3 OCH3 N

Q-2(R5'R6=K~ o H 5-Cl OCH3 OCH3 CH
Q-16(R5=F~,R6=CH3) O H 6-Br OCH3 OC~3 CH

~0 ~."~ 3.`~
~1 T~ble Ia Continued Q n a ~1 x Y z m P.C
Q-8(R5'=SCH3) O H 5-CH3 ~CH3 OCH3 CH
5 Q-8(R '=SCH ) O H 5-Cl OCH3 3 Q-l(R5~R6=H~ o H 3 3 3 Q ( 5' 6 ) O CH3 H OCU3 CH3 U
Q-8(R5'=SCH3) O H H OC2H5 CH3 CH
Q-l(R5,R6=H) O H H F OCH3 CH
Q ( 5' 6 ) O H H Br OCH3 CH
Q-3(R5,R6=H) O H H I OCH3 CH
Q-8(R5'=SCH3) O H H OCF2H OCH3 CH
Q-10(R5=CH3) O H H CH2F OCH3 CH
Q-18(R5=H,R6=CH3) O H H OCH2CH2F CH3 CH
Q-17(R5=H,R6=CH3) O H H OCH2CHF2 CH3 CH
Q-8(R5'=SCH3) O H H OCH2CF3 OCH3 CH
Q-lO(R5=CH3) O H H CF3 OCH3 CH
Q-2(R5,R6=H) O H H OCH2CH3 OCH3 U
Q-1(R5'R6=H~ o H H OCH2CH2F CH3 Q 5 3 O H H OCH2CF3 OC~3 Q ( 5 3) H H OCH3 H CH
Q-16(R5=H,R6=CH~) O H H CH3 OC2H5 CH
Q-8(R5'=SCH3) O H R CH3 CH20CH3 CH
Q-8tR5'=CH3) O H H OC2H5 ~HCH3 Q-17(R5=H,R6=CH3) O H H OCH3 ( 3) 3 a-8(R5'=SCH3) O H H OC}13 3)2 Q-18(R5=H,R6=CH3) 0 H H OCH3C2H~ CH
Q-12(R8=Cl) O H H OCH3 CF3 CH
Q-11(R5=CH3) O H H OCH3 SCH3 Q-18(R5=H,R6=CH3~ O H H CH3 OCH2CH=CH2 Q-lO(R5=H) O H H CH3 OCH C-CH
Q-13(R5=CH3) O H H OCH3 CH20CH2CH3 CH
Q-17(R5=H,R6=CH3) O H H CH3 2 2 3 Q-14(~5=H) O H H CH3 CH2SCH3 CH
Q ( 5' 6 ) 0 H H OC~3 3 7 CH

.b ~

Table Ia_Continued _Q_ n R ~l ~ Y Z m.p.C
O O
5 Q-lO(R5=C~3) o H H CH3 CH CH
o Q~ 5,R6=H) O H H CH3 CCH3 CH
Q-8(R '=SCH ) 0 H H OCH3 CH(OCH3)2 CH
Q-l(R5,X6=H) O H H CH3 CH(OCH3)2 N
lO Q~8(R5=SCH3) o H H OCH3 CH(OC2H5)2 CH
Q~2(R5,R6=H) O H H OCH3 CH(SCH3)2 CH
Q-3~R5'R6=H~o H H OCH3 C(CH3)~OCH3)2 CH
Q-8(R5'=SC~3)H H OCH3 CHo~ CH
O
Q-l8(R53H.R6=CH3) 0 H H CH3 CH ~ CH
o ~0~
Q-17(R5=H,R6_CH3) 0 H H OCH3 CH 1 CH

~O_ -CH
Q-8(R5'=CH3) 0 H R OCH3 CH CH
Q-lO~R5=H) 0 H H OCH3 OCF~H CH
Q-l4 3 2 CH

Q-8(R5'=SCH33 0 H H OCH3 CH ¦ N
~2 ,~CH2 Q-l(~5'R6=H~ O H H OCH3 CH ¦ CH

~ CH2 C~H5 0 H H OCH3 CH ¦ N
\CH2 C6H5 0 H H OCH3 C ¦ CH
CHz Table Ia_Continued Q n R Rl ~ Y Z m.P~oc Q l(R5'R6 H) 1 CH3 H OCH3 OCH3 CH
Q-l(R5,R6=H) 1 H H CH3 CH3 CH
Q-l(R5,R6_H~ 1 H H CH3 OCH3 CH
Q-l(R5,R6=H) 1 H H OCH3 OCH3 CH
Q ( 5~R6 H) 1 H H Cl OCH3 CH
Q~ 5=H,R6=CH3) 1 H H OCH3 OCH3 CH
Q-l(R5=H~cH3~R6=H) 1 H H OCH3 OCH3 CH
Q-2(R5.R6=H) 1 H H CH CH CH
Q (R5,R6 ~I) 1 H H OCH3 OCH3 CH
Q-2(R5,R6=H) 1 H H CH3 O~H3 C~I
15 Q ( 5'R6 H) 1 H H Cl OCH3 CH
Q-2(R5=CH3,R6=H) 1 H H OCH3 OCH3 CH
Q-2(R5_H,R6=C~3) 1 H H OCH3 OCH3 CH
Q (R5'~6 H) 1 H H CH3 CH3 CH
Q-3(R5,R6-H) 1 H H CH3 OCH3 CH
Q-3(R5,R6=H) 1 H H OCH3 OCH3 CH
Q-3(R5,R6=H) 1 H H Cl OCH3 CH
Q-3(R5aCH3;R6=H) 1 H H OCH3 OCH3 CH
Q-4(~5,R6=H) 1 H H CH3 CH3 CH
Q-4(R~,R6=H) 1 H H OCH3 CH3 CH
Q-4~R5'R6=H~ 1 H H OCH3 OCH3 CH
Q-4(R5,R6=H~ .1 H H Cl OC~3 CH
Q ( 5'~6 H) 1 H H OCH3 OCH3 CH
Q (R5'~6 El) 1 H H CH3 CH3 CH
Q-5(R5,R~=H) 1 H H CH3 OCH3 CH
30 Q-5(R5,R6=~] 1 H H Cl OCH3 CH
Q-6(R5=H) 1 H H OCH3 OCH3 CH
Q-6(R5=H) 1 H H CH3 OCH3 CH
Q-S(R5=H) 1 H H CH3 CH3 Q-6(R5=H) 1 H H Cl OCH3 C~
Q-8(R5'=H) 1 H 3 CH3 CH
Q-8~R5'=H) 1 H H OCH3 OCH3 CH

Table Ia Continued Q n R 1 X Y Z P.4C
Q-8(~5'=H) l H H CH3 OCH3 C~
Q (R5 H) l H H Cl OCH3 CH
Q-9~R5=H) l H H OCH3 OCH3 CH
Q-9(R5a~) l H H CH3 CH3 CH
Q-l0(R5=H) l H H OCH3 OCH3 CH
Q-l0(R5=~) l H H CH3 OCH3 CH
Q-l0(R5aH) l H H Cl OC~3 CH
Q-ll(R5=H) l H H OCH3 OCH3 CH
Q-ll(R5=H) l H H c~3 OCH3 CH
Q-12(R8=H) CH3 CH3 CH
Q-12(R8=H) l H H Cl H3 CH
Q-13(R5=CH3)l H H OCH3 OCH~ CH
Q-l4(R5=H) l H H CH3 CH3 CH
Q-14(R5=H) l H H OCH3 OCH3 CH
Q-l4(R5=H) l H H CH3 OCH3 CH
Q-14(R =H) l H H Cl OCH CH

Q-15(R5=H) l H H OCH3 OCH3 CH
Q-l~(R5=H,R6-EI)l H H CH3 O~H3 CH
Q-16(R5=~,R~=H)l H H CH3 CH3 CH
Q-16(R5=H,R~=H)l H H Cl OCH3 CH
25 Q ~ 5 ~ 6 )l H H CH3 CH3 CH
Q-17(R5=H,R6=H)l H H OCH3 OCH3 CH
Q 18(R5=~,~6=H)l H H CH3 C~3 CH
! Q-18(R5=H~R6=~'l H H Cl OCH3 CH
Q-l8(R5=H.R~=H)CH3 OCH3 CH
Q-19(R -CH R =H)l H H OCH3 OCH3 CH
Q-20~S,R6=CH3)l H H OCH OCH CH
Q-22(R5,~6,R7=H)H3 OCH3 CH
Q-24(R5,R6,R7=H)l H H OC~3 CH3 CH

~-28(R~,R6=H,n'=0~ l H H OCH3 OCH3 CH
Q-30(R5=H~Rg~Rlo=CH3) l H H OCH3 OCH3 CH
~-33(R~,R~=H~O 3 OCH3 CH

Table Ia Continued ~ n R Rl ~ y z m.~.C
Q-35(Rll,Rl2=OCH3) l H H OCH3 OC~3 CH
C6H5 l H H OCH3 OCH3 CH
C6H5 l H H OCH3 CH3 CH
Q-37(R5=H l H H OCH3 OCH3 C~
Q-38(R5=H) l H H OCH3 OCH3 CH
Q-39(R5,R$=H) l H H OCH3 OCH3 CH
Q-l(~5'R6-H) l H H OCH3 OCH3 N
Q-2(R5,R6=H) l H H CH3 OCH3 N
Q-8(R5'=CH3) l H H CH3 OCH3 N
Q-8(R5~,=CH3) l H H OCH3 OCH3 Q-12(R8=Cl) l H H OCH3 OCH3 N
Q-~7(R5=H.R6-CH3) l H H OCH3 OCH3 N
Q-l8(R5=H~6=C~3) l H H OCH3 OCH3 N
Q-22(R5,R6,R7=H) l H H OCH3 CH3 N
Q-26(W~=S) l H 3 OCH3 N
Q-27~R5,R6=H~n~=l) l H H OCH3 OCH3 N
Q-30(R5,Rg,Rlo=H) l H H OCH3 OCH3 N
Q-33~R5'~6=H~ l H H OCH3 OCH3 N
C6H5 l H H CH3 OC~3 N
C6H5 l H H OCH3 O~H3 25 Q ( 5~ 6 H) l H 5-Cl OCH3 OCH3 N
Q-l6(R5=H,R6=CH3~ l H 3 CH3 CH
Q-3(R5'=SCH3) l H 5 CH3 OCH3 OCH3 C~
Q ( 5 H3) l H 5-Cl OCH3 CH3 N
Q-l(R5,R6=H) l CH3 5-C~13 OCH3 c~3 Q-l~R5~R6=H~ l CH3 H OCH3 CH3 N
Q-8(R5'-SCH3) l H H OC2H5 CH3 CH
Q-l(~5,R6=H) l H H F OCH3 CH
Q-2(R5,~6=H) l H H B~ OCH3 C~
Q-3(R5'R6=H) l H H I OC~3 CH
35 Q ( ~ ,R SCH3) l H H OCF2H OCH3 CH
Q-l0(R5=CH3~ l H H CH2F ~C~3 CH

;~ r~ r~

Q n R 1 ~ Y 2 ~ p-C
Q-18~R5=H,~6=CH3) 1 H H OCH2C~2 3 Q-17(R5=H,~6=C~3) 1 H H 2 2 3 CH
Q-8tR5'=SCH3) 1 H H ~H2GF3 OCH3 CH
Q-lO(a5=CH3) 1 H H CF3 OCH3 CH
Q-2(R5,R6=H) 1 H H CH2cH3 OCH3 0-l(R5~R6=H) 1 H H OCH2CH2F CH3 Q ( 5 3) 2 3 3 Q-9(R5=CH3) 1 H H oc~3 H CH
Q-16(R5,R6=H) 1 H H CH3 OC2}l5 CH
Q-8(R5'=SC}13) 1 H H CH3 CH~OCH3 CH
Q-8(R5'=CH3) 1 H H OC2H5 ~HCH3 U

Q-8(R5'=SCH3) 1 H H OCH3 U(CH3)2 Q-18(R5=H,R6=CH3) 1 H H OC~3 C2H5 CH
Q-12(R8=Cl) 1 H H OCH3 CF3 CH
Q-ll(R5=CH3~ 1 H H OCH3 SCH3 Q-18(R5-H,R6=CH3) 1 H H CH3 OCH2CH=CH2 -lOtR5=CH3) 1 H H CH3 OCH C-CH
Q-13(R5=CH3) 1 H H OCff3 CH20CH2CH3 CH
Q-17(R5~H,R6=CH3) 1 H H CH3 OCH2CH20CH3 CH
Q-14(R5=H) 1 H H CH3 CN2SCH3 CH
Q 5' 6 1 H H OCH3 i-C3}l7 CH
Q-lOtR5=CH3) 1 H H C~13 CH CH
o Q-l~R5,R6=H) 1 H H Cff3 CC~3 CH
Q 5 3 1 H H O~H3 CH(OCH3)2 CH
Q-l(R5,R6=H) 1 H H CH3 CH(OCH3)2 Q-8(R5=SCH3) 1 H H OCH3 CH(OC2H5~2 CH
Q-2(R5,R6=H) 1 H H OCH3 CH(SCH3)2 CH
Q-3~R5'R6=H~ 1 H H OCH3 C(CH3)(0CH3~2 CH

k~

'~ r7' ~
~7 ~Table Ia Continu~d O ~ R Rl ~1 Y Z m. P . C
S Q-8 (R5 ~ =SC~13 ) 1 H H OCH3 CH ~ CH

Q~ R5=H~ p~6=cH3 ) 1 H H C~3 CH ~ CH

Q-l7(R5=H,R6=CEI3) 1 H H OCH3 C'H ~

~o CH
Q-8 (R5 ' =CH3 ) 1 H H OCH3 CH ~~ 3 CH
Q-lO (R5=H) H OCH3 OCF2H CH
Q-14 (R5=H) OCH3 5CF2H CH
/ CE~2 Q-8 (R5 -SCH3 ) 1 EI H OCH3 CH ¦ N

- / CH;~
Q-l(R5,R6=H) l H H OCH3 C ¦ CH
~H2 C6~5 l H HOCH3CH ¦ N
2 5 CEI;2 ~ CH2 ~6H5 3C~ ¦H CH

Q 35 ~R11=R12=CH3 ) 1 H ~OC~3 ~ CH CH

~ CH2 Q~39 (R5=R6=H) l H HOCH3 CH ¦ CH

r;~" ~/D~ `s~r ~8 ~sd QA al ~ y Q~ 5~a6~OC~3 O~H3 ~H
Q-5~,a6-H)H3 OCH3 CH
Q-0(~5'-H)2 ~ H OCH3 OC~3 Q-14~5n~)2 H ~ OCH3 OC~3 CH
Q-16(~5~H.~fi-CH3) 2 H H OCH3 3 10 Q l(RS'~6 H)2 ~ H OCH3 OC~3 Q-lO~R5=H)2 ~ H OCH3 OCH3 Q-12(R8~H)2 H H C~3 OC~3 Q-13(R~'~,R6~CH3) 2 H H O~H3 OCH~ N
Q-24(~5,R6,R7~H) 2 H H OCH3 ~CH3 N
Q-27(~5.R6~H,n'~l) 2 ~ H 3 ~H3 N
Q-33(R5,~6,3H) 2 H H OC~3 OCH3 Q-371~5.R6-H) H OCH3 ~C~13 CH
Q-7(R5,R7=CH3,R6=H) O H H CH3 OCH3 CH 220-224 Q-7(R5,R7=CH3,R6=H) O H H CH3 CH3 CH 212-216 Q-7(R5,R7=CH3,R6=H) O H H Cl OCH3 CH 193-195 20 Q-7(R5,R7=CH3,R6=H) O H H OCH3 OCH3 N 190-193 4a rabl~ Ib ~1 1 ~ SO2NHCON
~CH2)n ~2 Yl --Q n R 1 1 1 m.p.oc Q~ 5,R6=H) O H H CH3 O
Q-2(R5,R6a~) 0 H H CH3 O
Q-3(R5,R6=H) O H H CH3 O
Q-4(R5,R6=H) 0 H H CH3 O
15 Q-7(R5~R6~R7=H) 0 H H CH3 O
Q-B(R5'=SCH3) 0 ~ H CH3 O
Q-8(R '=CH ) 0 H H CH3 O
Q-8(R5'=H) O H H CH3 O
Q-9(R5=CH3) o H H CH3 O
20 Q~1(R5=C~3) 0 H H CH3 O
Q-14~R5=H) O H H CH3 Q-l~(R5,R6.,H) O H H CH3 o Q-17(R5,R6=H) O H H CH3 O
~ ( 5' 6 ~1) 0 H H CH3 O
25 Q-2l(R5~R6~R7=H) O H H CH3 o Q-22(R5,R6,R7=H~ O H H CH3 O
Q-24(~5,R6,R7=H) O H H CH3 O
Q-27(R5,R6=H,n'-o) O H H CH3 O
Q ( 5~ 9~ 10 H) O H H 3 30 Q-33(R5~R6=H) o H H CH3 o Q-8(R5'-SCH3) 0 H H OCH3 O
Q-l(R5,R~=H) o H 2H5 Q ( 5 3) H H OCF2H O
Q ( 5 3) H H CH3 CH2 35 Q-~R5 =SCM3) 0 H H OCH3 CH2 ~g ~, r r~ ~ ~ 2~ r"~

T_~lq Ib Continlled Q n ~ R
Q ( 5 ' 6 H) 1 H H CH3 Q-2(R5,R6=H) 1 H H CH3 0 Q-~ (R~ ' =SCH3 ) 1 H H CH3 o Q 8(R5 C~3~ 1 H H CH3 0 Q-14 (P55=H) 1 H H CH3 0 Q-16(R5,R6=H) 1 H H CH3 0 Q-17(R5,R6=H) ~ H H CH3 0 Q-18(R5,R~=H) 1 H H CH3 0 Q-33(R5,R6=H) 1 H H CH3 0 Q-l~F~5'R6=H~ 1 H C2H5 0 Q~~ (R5 ' =CH3 ) 1 H H OCF2H O
Q-8 (R5 ' =SCH3 ) 1 H H OCH3 C~2 Q-B (R5 ' =CH3 ) 2 H H CH3 o Q-14 (R5-EI) 2 H H CH3 0 Q-8 (R5 ' =SCH3 ) 2 H C2HS 0 20 Q 33 ~ ~R5,R6 H) 2 H H CH3 0 ~.,, f~ ~ `f~

able Ic N X
5 ~ 502NHCO~
N' (CH2)nQ

_Q_ n R al 1 m.p.C
Q-l(R5,R6=H) O H H CH3 Q-2(R5,R6=~) 0 H H OCH3 Q-3(R5,R6~H) o H H 2 5 Q-4(R5,R6=H) O H H CH3 15 Q-7(R5,R6,R7=H) O H H CH3 Q-~(R5'=SCH3) 0 H H OCH3 Q-8(R5'=CH3) 0 H H OCH3 Q-8(R5'=H) O H H CH3 Q-9~R5=CH3) 0 H H OCF2H
20 Q-lO(R5=CH3) 0 H H CH3 Q-14(R5=H) o H H OCH3 Q-16(R5=H,R6=C~3) 0 H H CH3 Q-17(R5=H,R6=~H3) 0 H H OCF2H
Q-l~(R5=H,R6=CH3) 0 H H OCH3 Q ( 5,~6,R7 H) O H ~ ~CH3 Q-22(R5,R6~R7=H) O H H CH3 Q-24(R5,R6,~7=H) O H H CH3 Q-Z7(R5,R6=H,n'=o) o H H O~H3 Q-30(R5,R6,Rlo=H) O H H OCH3 30 Q-33(R5,R6=H) H H OCH3 Q~l(R5,~6=H) 1 H H CH3 Q-2(R5,R6=H) 1 H H CCH3 Q ~(R5 CH3) 1 H H OCH3 Q-8~R5'=SCH3) 1 H H CH3 35 Q-lO(R5=CH3) 1 H H OC2H5 ;~

s~
Ta_1e Ic Con~nued Q n R Rl Xl ~. p . C
Q-14 (P~5=H) 1 H H OCH3 Q-17 (R5=H, R6=~3 ) 1 H H OCF2EI
Q-~l(R5,R6,R7=EI) 1 H IH OCH3 Q-33 (R5.P~6=H) 1 H H OCH3 ~2-8 (R5 ' -CH3 ) 2 H H C~3 Q-27(R,R6=H,n'=1) 2 H H OC~13 Q-24~R5,E~6=H) 2 H H OCH3 Q-l(R5,P~6=H) 2 H H CH3 Q-4 (R~,,, R6=H) 2 H C2EI5 Table Id N X
~ S02NHCON ~ O-- S

N (CH2)nQ Y2 --Q n R 1 1 2 m.p.oC
Q-l(R~,R6=H) 0 H H CH3 CH3 Q-2(R5,R6=H) o H H OCH3 CH3 Q-3(R5.R6~H) 0 H HC2H5 H
Q-4(R5,R6=H) 0 H H CH3 CH3 15 Q-7(R5.~6.R~=H) 0 H H CH3 C~3 Q-8(R5~zSCH3) o H H CH3 ~H3 Q (R5 CH3) o H H CH3 CH3 Q-8(R5'=H) 0 H H CH3 C~3 Q-9(R5=C~3) o H HOCF2H CH3 20 Q~1(a5=CH3) 0 H HCH3 CH3 Q-14(R5=H) 0 H HCH3 CH3 Q-16(R5,R6=H) o H HCH3 CH3 ~-17(R5,R6=H) o H H2 CH3 Q-1~3(R5,R$=H) O H H~H5 CH3 25 Q-2l(R5~R~R7=~) 0 H H CH3 C~3 Q-22(R5,R6,R7~H) o H H OCH3 H
Q-24(~5,R6,R7-H) o H H OCF2H CH3 Q-27(R5,R6=H,n'=o) o H H CH3 CH3 Q-30(R5,Rg,Rlo-H) H H 3 ~3 30 Q-33(R5,R~-H) o H H CH3 CH3 Q-1(R5,R6=H) 1 H ~ C~3 c~3 Q-25R5,R6=H~ 1 H H OCH3 CH3 Q-3(R5,R6-H) 1 H 2H5 H
Q-8(R5'=SCH3) 1 H H CH3 CH3 35 Q-8~R5~ 3~ 1 H H CH3 c~3 ~q Ta bl e I d Cont 1 nued Q n R Rl Xl 2 m. P. C
Q-14 (R5=H) 1 H H CE13CH3 Q-16 (R5, R6=E~) 1 H H CH3 CH3 Q-18 (R5 . R6=H) 1 H H OC2H5 CH3 Q-21(R5,R6,R~=H) 1 H H CH3 CH3 Q-27(R5,R6=H) 1 H H CH3 CH3 10 Q ( 5 . R6 ~I~ 1 H H CH ~CH3 Q-3B(R5,R6=H) 1 H H CH3 CH3 Q-l(R5.P(6=E~) 2 H H CH3 CH3 Q-~ (R ' -SCE~ ) 2 H H CH3 CH3 Q-8 (R5 ' -CH3 ) 2 H H CH3 CH3 Q-33(R5,E~6=H) 2 H H CH3C,H33 T~

al~ S02N~CON~

N (CH2)mQ

Q ~ a ~1 ~2 Y3 ~C
Q-l(a50R6-~) ~ E~ CH3 ~H3 Q-2(R5,Rt; ~H) O H E~ OCH3 CH3 Q-3 (R5 .P~6.R~ 0 H H OCH3 C~2~5 Q 4t~5'R6 ) O H ~ CH3 C~3 Q ( 5 ' 6 ' 7 ) O H El CH3 ~H3 Q-B (R5 ' JSCH3 ) o El H C~13 CH2CF3 Q-8 (R5 ' 8CH3 ~ O H H CH~ CE12CF3 Q-~(a5l=H~ O H H CE~3 CH3 Q 9 ( X5 CH3 ~ o H H OCH3 CH3 Q 10 (P~5 CE13 ~ O H H CH3 CH3 Q-14 (R5eH) O H H CH3 C2H5 Q-lij~R5=~,R6 ~EI3) 1~ H ~II3 ~H3 Q-l?(R5~H,B~=C~3) H H OC 3 2 3 Q-18 (RS-H, R6-CE~3 ) O H H OC~3 CH3 Q-21(R5,R6,R75H) O H H CH3 c~3 2 Q tR5,R6,R7 E~) O ~ E~ OCH3 C2~5 Q-24(R5,R6,R7=H) O H H OCE~3 CH3 S;?-27~5,R6'H, ~ l) 0 ~ H CH3 C~3 9 ' 10 H) o iH H CH3 CE13 Q-33 (R5 .P~6~H) O H H CH3 CH3 Q 1 (R5, R6 E~ 1 H H CH3 CEI3 Q-2~R5,~6~R~ 1 H 3 c~3 Q-8 (E~5 ' ~`CH3 ) 1 M 8 CH3 C2E~5 Q-8 (R5 ' ~SCH3 ) 1 H H CH3 ~EI2CF3 Q 9 (E~5 CH3 ~ 1 H H OCH3 CH3 3 5 Q- 10 ( R5 ~CH3 ) 1 El IH C}13 3 Tab_ e Ie Continued Q n ~ P~l X2 3 m.p.C
Q-14 (a5~H) 1 H H CH3 C2H5 Q-16 (R5aH, R6=C~13 ) 1 H H CE~3 c~3 Q-27 (P~5, R6=H) 1 H H ~H3 c~3 Q-33(R5,R6=H) 1 H H CH3 CH3 Q ( 5, R 6 H ) 2 H H CH3 CH3 Q-a (R5 ~ =~CH3 ~ 2 H ~ ~3 CH3 Q-10 Z H H OCH3 C~12CF3 Table~If R1 ~ SO~NHCON_~H2~
N (CH2) nQ 3 ~ R 1 3 m. p . oC
Q-l(R5,R6=H) O H H CH3 Q-2(R5,R~=H) O H H CH3 Q-3(R5,R6.H) o H H CH3 Q-4(R5,R6=H) 0 H H OCH3 15 Q~7(R5~R6~R7=~) o H ~ OCH3 Q-9(R5'=CH3) 0 H H CH3 Q-8(R5~-SCH3) o H H OCH3 Q-8(R5'=C~3) 0 H H CH3 Q-9(R5=CH3) o H H CH3 20 Q~1(R5=C~3) 0 H H OCH3 Q-14(R5=~) 0 H H OCH3 Q-16(R5,R6=H) o H H CH3 Q-17(R5.R~=H) H H CH3 Q-18(R5,R6=H) 0 H H OCH3 25 Q-21(R5,R6,R7=H) O H H ~H3 Q-2~R5~R6~R7-H) o H H OCH3 Q-24(R5,R6,R7=H~ o H H CH3 Q-27(R5~R~ n'=O) H H C~3 Q-30~R5.Rg.Rlo=H) O H H OCH3 30 Q-33(R5.R6=H) O ~ H CH3 Q-38(R5,R6=H) O H H CH3 Q-l(R5,R6=H) 1 H H OCH3 Q-2(R5,R6~) 1 H H CH3 Q ( 5 3) 1 H H CH3 35 Q~~(R5~=SCH3) 1 H H OCH3 /

Table T Continued ~ n R Rl X3 Q-lO(F~5=CH3~ 1 H H CH3 Q-14 (R5-H) 1 H H CH3 Q-16(R5,R6-~1) 1 H H OCH3 Q-18(R5,R6=H) 1 H H OCH3 Q-Z7(R5,R6=H) 1 H H CH3 10 Q-3~tR5~R6=H) 1 H H OCH3 Q-l(R5,P~6=H) 2 H E~ OCH3 ~--8 (R5 ' =CH3 ) 2 H H OCH3 s~

. N
Rl ~ SO~NHCSN~

N (C~{~)nQ

_Q_ n R R1 X Y Z
Q-l(R5.R6=~) 3 H3 CH
Q-l(R5,R6=H)H OCH3 OCH3 CH
Q-2(R5,R6=H)o H H OCH3 C~3 CH
Q-3~R5,R6=H)H OC~3 OCH3 CH
Q-4(R5,R6-H)0 H H OCH3 OCH3 CH
15 Q-l(R5'R6=H) H H CH3 OCH3 N
Q-8(R5'=CH3)O H H 3 CH3 CH
Q-9(R5-CH3)O H H OCH3 ~CH3 CH
Q-lO(R5=CH3)O H H CH3 OCH3 CH
Q-14(R5=H)H H OCH3 OCH3 CH
Q-16(R5,R6=H)0 H H OCH3 OCH3 CH
Q-17(R5=H,R~=CH3) O H H OCH3 OCH3 CH
Q-21(R5,R6.R7=H) O H H OCH3 OCH3 CH
Q-22(R$,R6.R7=H) O H H OCH3 OCH3 CH
Q-24(R5,R6.R~=H) O H H OCH3 OCH3 CH
Q-33(R5,R6=~H OCH3 OCH3 CH
Q ( 5 3)1 H H OCH3 O~H3 CH
Q-8(R5'=CH3)1 H H OCH3 CH3 N
Q-8(R5'=CH3) ~ ~ CH3 OCH3 Q-8~5'=CH3)H OCH3 OCH3 CH

Table_IIa R 1~ 802NHCON -<~
R N ~

Q n R Rl X Y Z m P.C
Q l(R5,R6 H) O CH3 H OCH3 OCH3 CH
Q-l(R5~R~=H) o HH CH 3 CH3 CH
Q-l(R5,R6=H) O HH CH3 OCH3 CH
Q-l(R5,R6=H) O HH OCH3 OCH3 CH
Q-l(R5,R6=H) O HH Cl OCH3 CH
15 Q-l(R5=H,R6= CH3) 0 H H OCH3 OCH3 CH
Q-l(R5=CH3,R6=H) ~ H H OCH3 OCH3 CH
Q-2(R5,R6=H) O H H CH3 ~H3 CH
Q-2(R5,R6=H) O H H OCH3 OCH3 CH
Q ( 5' 6 ) O H H CH3 ~CH3 C~I
Q-2~R5'R6=H~ O H H Cl OCH3 CH
Q-2(R5=CH3,R6=H) O H H OCH3 OCH3 CH
Q-2(R5=H,R6=CH3) 0 H H OCH3 OCH3 CH
Q ~ 5' 6 ) O HH CH3 CH3 CH
Q-3(R~,R6=H) O HH CH3 OCH3 CH
Q ( 5~ 6 H) O HH OCH3 OCH3 CH
Q-3(R5,R6=H~ O HH Cl OCH3 CH
Q-3(R5=CH3,R6_H) O H H OCH3 OCH3 CH
Q-4(R5'R6-H~ O HH CH3 CH3 CH
Q-4(R5,R~_H) o H3 3 CH
30 Q-4(R5,R6=H) O HH OCH3 OCH3 C~
~-q(R5'R6=H) 0 HH Cl OCH3 CH
Q-5(R5,R6=H) O HH OCH3 OCH3 CH
Q-5~R5,R6=H) O HH CH3 CH3 CH
Q-5(R5,R6=H~ O HH CH3 OCH3 C~I
35 Q-5(R5,R6=H) O HH Cl OCH3 CH

6~

r P ~ r~

Table I~a Continued _Q_ n R Rl ~ y Z m.p.oC
Q-6~R5=H) O H H OCH3 OCH3 CH
Q-6(R5-H) O H H CH3 OCH3 CH
Q-6(R5--H) O H H CH3 CH3 CH
~-6(R5=H) 0 H H Cl OCH3 CH
Q-7(R5,R6,R7=H) O H H CH3 CH~ CH
Q-7(~5,R6,R7=H) O H H OCH3 OCH3 CH
Q-7(R5,R6.R7=H) O H H CH3 OCH3 CH
Q-7(R5,~6,R7=H) O H H Cl OCH3 CH
Q-7(R5,~7=CH3;R6=H) o H El OCH3 OCH3 CH
Q-8(R5'=H) H H CH3 CH3 CH
~-a (R5'=H) O H ~1 OC~3 OCH3 CH
Q-8(R5'=H) O H H H3 OCH3 CH
Q-8(R5'=H) O H H Cl OCH3 CH
Q-8(R5~=CH3) O H H OCH3 OCH3 CH
Q-8(R5'=CH3) O H H CH3 OC~3 C~
Q-~(R5'=CH3~ O H H CH3 CH3 CH
Q-8(R5'=CH3) O H H Cl OCH3 CH
Q-8(R5~=CH3) CH3 H OCH3 OCH3 CH
Q ( 5 C2HS) O H H CH3 CH3 CH
Q-8(R5'=C~H5) o H H OCH3 OCH3 CH
Q-B(~5'=C2~5) o H H CH3 OCH3 CH
Q-8(R5'=C2H~ H H Cl OCH3 CH
Q-8(~5'=SCH3) O H H OCH3 OCH3 CH
Q-8(R5'=SCH3) O H H CH3 OCH3 ~H
Q-8(~'=SCH3) O H H CH3 C~I3 CH
Q-8(R5~=SCH3) O H H Cl OCH3 CH
Q ( 5 SC2H5) O H H CH3 CH3 CH
Q-8(R5'=SCzH5) O H H OCH3 OCH3 CH
Q-8(R5~=SC2~5) O H H CH3 OCH3 CH
Q-B(R5~SC2~5) O H H Cl OC~3 ~H
Q-8(R5~=SCH2CH=CH2) o H H OCH3 OCH3 CH

i~. fio ..~ .

~d Q n R Rl ~ y Z ~.P C
Q-g(~$'~SCH2CH~CH2) 0 H H CH3 3 Q-8(R5'~SCH2CH3CH2~ H H ~H3 CH3 Q-8(~5'~scH2cH~cH2~ 0 N ~ Cl 3 Q-8(R5'~SCF2H)O H3 OC~3 CH
Q-8~R5'~S~F2~)3 CH3 C~
Q-8(R ~ nSCF H)O H H OCH3 CH3 CH
~-~(R5'aSCF2H)O ~ H Cl ~CH3 CH
Q-~3 (R5 ~ ~SC 3H7 ) O H Hl OCH3 OCE~3 Q-8(a5'-SC3H7)H3 OCH3 CH
Q-8(R5~SC3H7) H H. Cl OCH3 CH
~ 5'sOCH3)H3 OCH3 ~
Q-8(R5~-OC2H5)0 H H OCH3 OCH3 CH
Q-9(R5-H)O H H OCH3 OCH3 CH
Q-9(R5~H)O H H CH3 OCH3 C~l Q-9(R5=H)CH3 CH3 CH
Q-9(R5=H)O H H Cl OCH3 CH
Q-9(R5=CH3)0 H H OCH3 OCH3 CH
Q t 5 3)o H H CH3 OCH3 CH
Q (R5 CEI3)3 CH3 CH
( 5 CH3)0 H H Cl OCH3 C~
Q-lO(R5=H)3 CH3 CH
Q-10(~5=~) ~3 CH3 CH
Q-10 (R5~H) H H CH3 OCH3 CH
Q-lO(R5aHO H H Cl 3 CH
Q-lO(.R5=CH3)o H H CH3 ~H3 CH 160-165 ~-lO(R5=CH3~0 H H OC83 OCH3 CH 169-173 Q lO(R5 C~3)0 H H ~H3 OCR3 CH
Q-lO(R5=CH3)o H H Cl OCH3 CH 162-166 Q-ll(R5~H)O H H OCH3 OCH3 CH

Q-12~8=H' 3 3 Q-12(R85Cl)O H H OCH3 OCH3 CH

TabL~ IIa Contirlued Qn R R 1 ;K Y Z g~
Q 13(R55CH3)H3 OCH3 CH
Q-14(R5=H)O H H OCH3 OCH3 CH
~-14(R5=H)O H H CH3 OCH3 CH
Q-14(R5=H)O H H Cl OCH3 CH
Q-15(R5=H)O H H OCH3 OCH3 CH
Q-16(R5~R6=H)O H H C~13 C~3 CH
Q-16(R5,R6=H)H3 OCH3 CH
Q-16(R5~R6=H)O H H C~3 VCH3 CH
Q-16(Rs,R6=H)O H H Cl OCH3 CH
Q-17(R5~R6=H)O H H OCH3 OCH3 CH
Q~17(Rs~R6=H~3 OCH3 CH
Q-17(R5~R6=~o H H CH3 CH3 C'H
Q-17(Rs,R6=H)O H H Cl OCH3 CH
Q ( 5' 6 )O H H OCH3 OCH3 CH
Q~13~5~R6=H)3 OCH3 CH
Q-18(R5,R6=H)o H H CH3 CH3 CH
Q-18 (R5, R6=H)O H H Cl OCH3 CH
Q l9(R5=CH3~R6=H) 3 3 CH
Q-20(R5,R6=CH3) OCH3OCH3 CH
~-21~R5~a6~R7=H~ 3 3 Q-22(R5,R6,R7=H) O H HOCH3OCH3 CH
25 Q-23~R5~R6~R7=H~ H3 OCH3 CH
Q-24(R5,R6,R7=H) O H HOCH3CH3 CH
Q-25(R5,R6,R7-H~ 3 OCH3 CH
Q-26(W~=0) 3 OCH3 CH
Q-27~R5~R6_H,n~=O)O H H OCH3 OCH3 CH
Q-28(R5,R6=H,n~=O)O H H OCH3 OCH3 CH
Q-29(R5~R6=H,n~-O)O H H OCH3 OCH3 CH
Q-30(R5=H;Rg,Rlo=oCH3) 0 H H OCH3 OCH3 CH
Q-30[R5=H;Rg~Rlo-CH3) O H H OCH3 OCH3 CH

Q ( 9' 10 ) O H H OCH3 OCH3 CH

J--~r~ ~ ~ F ~

Table IIa_Contirlued ~ r. p~ a1 B Y z m. P . oc Q 32(R9'RlO H) O H H OCH3 OCH3 CH
Q-~3(R~,R6-H) O H H OCH3 OCH3 CH
Q-34(R5,R6=H~ O H H OCH3 OCH3 CH
Q-35(Rll'Rlz=CH3~ H T1 OCH3 OCH3 CH
Q-36(Rll,Rl2=CH3) o H H OCH3 OCH3 CH

~6H5 0 H H OCH3 CH3 CH

C6H5 0 H H Cl OCH3 CH
Q (R5.R6 ~) O H H CH3 OCH3 N
Q-2(R5.R6=H) o H H OCH3 OCH3 N
Q-3(R5=CH3,R6=H) o H H OCH3 OCH3 N
Q-8(R5'=CH3) o H H CH3 OCH3 N
Q-8(R5'=SCH3) 0 H H OCH3 OCH3 N
Q 9(R5=CH3) o H H CH3 OCH3 N
Q-lO(R$=CH3) O H H CH3 OCH3 Q-l2(R8=Cl) ~ H H CH3 OCH3 N
Q-~7 0 H H OCH3 CH3 N
Q-l8 O H H CH3 OCH3 N
Q-l8 O H H OCH3 ~CH3 Q-22~R5,R6,R7--H) o H H CH3 OCH3 N
Q-26(~'=S) O H H CH3 OCH3 Q-27(R5,Rs=H,n'=o) O H H CH3 OCH3 N
Q-27(R5,R6=H,n'=O) O H H OCH3 OCH~ N
Q-30(R5,Rg,Rl~=H~ o H H CH3 OCH3 N
Q-30~R~,R~,Rlo=H) O H H OCH3 OCH3 N
Q-33(R5,R6=H) o H H C~I3 OCH3 C6~5 O H H C~3 CH3 Q-2(R5'R6=H~ O H S-Cl OCH3 OCH3 CH

~ o~L~

Tubl~ Cont~nued ~Q_ n R 1 ~ Y Z m p.~C
Q 16~R5,R~=H) O H 6 ~r OCH3 OCH3 CH
5 Q-8(R '-SCH ) O H 5-CH3 OCH3 OC~3 ~l Q-3(R '=SCH ) O H 5-Cl OCH3 3 Q-1(R5,R6=H) O H 5-CH3 OCH3 3 Q-1(R5,R6=H) O CH3 H OCH3 CH3 D
10 Q ( 5 3) H H OC2HS CH3 CH
Q-1(~5,~6=H) O H H F OCH3 CH
Q-2(R5,R~=H) O H M Br OCH3 CH
Q-3(R5,R6=H) O H H I OCH3 CH
Q-8(R5'=SCH3) 0 H H OCF~H OCH3 CH
Q-10(R5=CH3) 0 H H CH2F OCH3 CH
Q-18(R5=H,R6-CH3) 0 H H OCH2CH2F CH3 CH
Q-17(R5=H,R6=CH3) 0 H H OCH2CHF2 CH3 CH
Q-8~a5~=SCH3) 0 H H CH2cF3 OCH3 CH
Q-10(R5=CH3) 0 H H CF3 OCH3 CH
Q-2(R5,R6=H) O H H OCH2CH3 OCH3 Q-1(R5,R6=H) O H H 2 2 8 Q-3(R5'=SCH3) 0 H H OCH CF OCH
Q 5 3) 0 H H OCH3 H CH

Q-8(R '-SCH ) O H H CH3 CH20CH3 CH
Q 5 3) 0 H H OC2H5 ~HCH3 Q-17(~5=H,~6=CH3) 0 H H OCH3 3) 3 Q-8(R5'=SCH3) 0 H H OCH3 3 2 Q-1B~R5=H,R6=CH3) 0 H H OCH3 C2H5 CH
Q-12(R8=Cl) O H H OCH3 CF3 CH
Q~ 5=C~3) 0 H H OCH3 SCH3 Q-18(R5=H,R6=CH3) 0 H H CH3 OCH2CH=CH2 U
Q-1~(~5=H) O H H CH3 OCH C-CH

Q-13(R5=CH3) 0 H H OCH3 CH20CH2CH3 CH
Q-17(R5=H,R6=CH3) 0 H H CH3 2 2 3 .av.~ 3 6fi Tabl~ Ila Coneinued Q n R Rl X Y Z m.p.~C

o Q-lO(R5=CH3) o H H CH3 CH CH

Q-l(R5,R6=H3 o H H CH3 CCH3 CH
Q-8(R5~=SCH3) 0 H H OCH3 CH(OCH3)2 CH
Q-1(R5 R6=H) O H H CH3 CH(OCH3)2 N
Q-8(R5=~C~3) O H H OCH3 CH(OC2E~5)2 CH
Q-2(R5 R6=H) O H H OCH3 CE~(SCH3)2 CH
Q-3(R5,R6=H) Q H H OCH3 C(C~3) (OCH3)2 CH
Q-8 (R5 ~ =SCH3 ) O H H OCH3 CH ~ CH

,o~
Q 18 O H El CEI3 CEI ~> CH

/o-~
Q 17 O H H OC~3 CH ~ CH
,0 CH3 Q-B (R5 ~ =CH3 ) O H E~ OCH3 CE~ ~ CH
Q-10 (R5=H~ O H H OCH3 OCF2H CH

Z 5 / CH~
Q ~(R =SCH3) O H H OCH3 ~ IH2 N
~ CH2 Q-1~R5 R6=H) O H H OCH3 CH ¦ CH

~ CH2 C6~5 O H H OCH3 CH I ~

/ C~l~
35 C6H50 H H OCH3 C\ ¦ CH

Table II~ Continued Q n R Rl ~ y z m.~.C
Q-ltR5.R6SH) 1 CH3 H OCH3 OCH3 CH
5 Q~l(R5 R6~H) 1 H H CH3 CH3 CH
Q l~R5,~6~H) 1 H H CH3 OCH3 CH
Q-l(R5,R6=H) 1 H H OCH3 OCH3 CH
Q-1(~5,a6=H) 1 H H Cl OCH3 CH
Q-l(R5=H,R6=CH3) 1 H H OCH3 OCH3 CH
10 Q-l(R5=CH3.R6=H) 1 H H OCH3 OCH3 CH
Q-2 (R5, R6=H) 1 H H CH3 CH3 CH
Q-~(R5,R6=H) 1 H H OCH3 OCH3 CH
Q-2(R5,R6=H) 1 H H CH3 OCH3 CH
Q-2(~5,R6=H) 1 H H Cl OC~3 C~
lS Q~2(R5=CH3~a6-~) 1 H H OCH3 OCH3 CH
Q-2(R5=H,R6=CH3) 1 H H OCH3 OCH3 CH
Q-3(R5,R6=H~ 1 H H CH3 CH3 CH
Q-3(R5,R6=H) 1 H H CH3 OCE13 C~I
Q-3(R5,R6=H) 1 H H OCH3 OCH3 CH
20 Q-3(~5.R6=H) 1 H H Cl OCH3 CH
Q-3(R5=CH3: R6=H) 1 H H OCH3 OCH3 CH
Q~4(R5,R6=H) 1 H H CH3 CH3 CH
Q-4(R5,R6=H) 1 H H OCH3 CH3 CH
Q-4(R5,R6=H) 1 H H OCH3 OCH3 CH
25 Q~4(R5~R6=~) 1 H H Cl 3 C
Q-5(R5,R~=H) 1 H H OCH3 OCH3 CH
Q 5(R5,R6 H) 1 H H CH3 CH3 CH
Q-S(R5,R~=H) 1 H H CH3 OCH3 CH
Q 5(R5,R6=H) 1 H H Cl CH3 CH
30 Q-6(R5=H) 1 H OCH3 OCH3 CH
~-6(R5=H) 1 H H CH3 OCH3 CH
Q-6(R5=H) 1 H H CH3 CH3 CH
Q-6(~5=H) 1 H H Cl OCH3 ~H
Q-8(R5'=H) 1 H H ~H3 c~3 CH
35 Q~3(R5'=H) 1 H ~ OCH3 OCH3 CH

6~
Table ~Ta Continued _Q_n ~ Rl X Y Z m.P~oc Q-8(~5'=H~1 H H C~3 O~H3 CH
5 Q-8(R5'=H)1 H H Cl OCH3 CH
Q-9(R5=H)1 H H OCH3 OCH3 CH
Q-9(R5=H)1 H H CH3 CH3 CH
Q-10(R5=H)1 H H OCH3 OCH3 CH
Q~10(R5=H)1 H H CH3 OCH3 CH
10 Q-lo(Rs=H)1 H H Cl OCH3 CH
Q-ll(R5=H) H3 OCM3 CH
Q-ll(R5=H)1 H H C~3 OCH3 C~l Q-12(R8=H) CH3 CH3 CH
Q-12(R8=H)1 H H Cl OCH3 C~
15 Q-l3~R5=cH3)H3 OCH3 CH
Q-14(R5=H)1 H H CH3 CH3 CH
Q-14(R5=H)1 H H OCH3 OCH3 CH
Q-14(R5=H)1 H H CH3 OCH3 CH
Q-14(R5=H)1 H H Cl 3 20 Q-15(R5=~)1 H H OCH3 OCH3 CH
Q-16(R5,R6=H)1 H H CH3 OCH3 CH
Q-16(R5,R6=H)H CH3 ~H3 CH
Q-16(R5,R6=H) 1 H H Cl OCH3 CH
Q-17(R5,R6=H) 1 H H CH3 CH3 CH
25 Q-l6(R5~R6=H) 1 H H OCH3 OCH3 CH
Q-18tR5.R6=H~ 1 H H CH3 OCH3 CH
Q-13(R5,R6=H) 1 H H Cl OCH3 ~H
Q-18~R5,R6=H)OCH3 OCH3 CH
Q-19(R5=C~3,R6=~) 3 OCH3 CH
30 Q-2otR5~R6=cH3) OCH3 OCH3 CH
Q-22(R5,R6,R7=H) 1 H HOCH3 OCH3 CH
Q-24(R5,R6,R7=H) 1 H HOCH3 C~3 CH
Q-28(R5~R6=H,n'=1) 1 H HOCH3 OCH3 CH
Q-30(R5=H,Rg,Rl~=CH3) 1 H H OCH3 OCH3 CH

35 Q 33(R5.R6=H) 1 H HOCH3 5CEI3 CH

~9 Table_lIa Continued - Q e ~ Y z ~.oc Q ( 11~ R12 OCH3 ) ~ ~ H OCH3 OCH3 CH

~6H5 1 H H OCH3 CH3 CH
Q t 5 ~ ~6 H~ 1 H H OCH3 OCH3 CE~
5;?-3a(R5.R6~H) 1 E~ H OCH3 OCH3 CH
Q-39(1~5,R6sH) 1 H H OC~3 OC~3 ~E~
10 Q-l(~5~l~6~ H OCH3 OCH3 N
Q-2 (R5, R6~H) 1 H H CH3 OCH3 N
Q~ 5 C~3 ) 1 H H CE13 OCH3 N
Q- 8 ( R5 ' ,C~ ~ ) 1 H H OCH3 OCH3 N
Q-12 (R8-Cl ~ 1 H H O~H3 OCH3 N
15 Q-17(R5.R6=H) 1 H H CCH3 OCE~3 N
Q-18(El5,R6sH) 1 H 3 OCE~3 N
Q-22 (R5, R6 ~ R7=H) 1 H H OCH3 CH3 N
Q-26 (W'=O) 1 E~ H ~CH3 OCH3 N
Q-27 (R5, R6aH) 1 H H3 OCH3 N
20 Q-30(R5~E~g~Rlo~H3 1 H H OCH~ OCH3 N
Q-33(R5,R~=H3 1 H H OCH3 OCH3 N
~6R5 1 H H CH3 OCH3 N

Q-2(R5,Rg=EI) 1 H 5-Cl OCE13 OCH3 N
25 Q-16 (R5,R6=H) 1 lH 5-Br OCH3 OCH3 CH
Q-8 (R5 ' ~SCH3 ) 1 EI 3 O~H3 OCH3 CH
Q ( 5 SCE~3 ) 1 H 5-Cl C;CH3 CH3 Q-l(R50R6~H3 1 H 3 OCE13 CH3 N
Q ( 5 ~ R6 H~ 1 CH3 EI OCH3 CH3 N
30 Q-8 (R5 ' ~SCE13 ) 1 7I ~ OC2~5 CH3 CH
Q-l (P~5 ~ a6~E~) 1 H H F OCH3 CH
Q-2(R5,R6-H) 1 El H Br OCH3 C~
Q ~ 5 ~ 6 H ) 1 H H I OCH3 CH
Q-~ (R5 ' SCH3 ) 1 H H OCF2H OCE~3 CH
35 ~ (R5sC~13) 1 H H CH2F OCH3 CH

Tabl~ T~l C~on~tlnu~a _Q n a ~1 ~ y z m p.C
Q ~ 5 ' 6 1 H H OCH2CH2F 3 5 ' 6 ) 1 H IX C~12C~lF2 CH3 ~8t~ 8CH ) 1 ~l ~1 OCH2cF3 OC~{3 CH
~10(E~5~CH3) 1 H H CE'3 OCH3 Q-2(~5,E~6~1f) 1 H H OCH;!~H3 OCH3 N
~ ( 5 .a6 ) 1 H 1{ OCH2CH2Y CH3 Q-R~R5'~SCH3) 1 H H OCH~!cF3 OCH3 ~9~5~Cli3) 1 H H OCH~I H CH
Q ~ 5 ' 6 3 ) 1 11 H CH3 OC2~15 CH
~8 (~ ' 5SCH ) 1 H U C}13 CH20CH3 CH
L 5 ~ ~ 5 3 ) 1 H H OC2N5 ~IHCH3 s~l7~R5~H,a6DCH3) 1 H H OC~3 ( 3) 3 U
Q-8 ~ .SCH ) 1 H H OCH3 ~ 3 ) 2 11 Q ~ 5 ' 6 3 ) 3 ~2HS CH
Q-12(R8~Cl) 1 H H OCH3 3 Q-ll(R5.CH3) 1 H H OCH3 SCH3 Q-18tRs~H~6aCH3) 1 H H CH3 OCH2~=CH2 U
Q-lO~R5~ CH3) 1 H H CH3 OCH C--CH l~l Q-13(R5=CH3) 1 H 11 OCH3 2 2 3 CH
Q-17(Rs-H~R6~CH3) 1 H H ~!{3 OC312CH20CH3 CH

Q-14(~5-11) 1 H H ~H3 CH2SCH3 CH
Q ( 5 ~ 6 ) 1 11 ~ OC}~3 ~3 7 Q-lO(R5=CH3) 1 H H CH3 CHO CH
Q 5 ~ 6 1 M H CH3 COCH3 C}{
Q-3tR5~5SCH3] 1 H H OCI{3 CH(OCH3)2 ~{
Q--l ( Rs ~ lR6 aH) 1 H H CH3 CH ( OCH3 ) 2 El Q-8(Rs~3scH3l 1 H H OCH3 ( 2 5)2 CH
Q-2(E~5~R6~-H) 1 il H OCH3 CH(SCH3~2 CH
Q~3(E~5~ 5=H) 1 H H t~H3 C (C2{3)(OCH3~2 C}l ~inued ~ R ~1 X ~r Z
Q 8 (E~5 S~H3 ~ 1 H }IOCEI3 C!H~ CH

Q 1~ 5 E~6 E~) 1 H H~H3 CH ~ CH

Q- 17 ~ R5 ~RS H ) 3 CE~S ~ CH
O C~
~-8 ~a5 ' -C~3 ) 1 H HOCH3 Chor 3 CH
Q-lO(R5~H) CH3 OCF2H CH
Q-14 tR5=~l) OCH3 SCF2EI CH
~ CH2 ~-B(R5'~SCH3) H HOC~3 CH¦H N

~-1(R~"R6=H) OCH3 CHIH CH

Q l(R5'~6 H) 1 IH HOCH3 CH¦ 2 CH

'~H2 ~6H5 1 lH HOCH3 Ci~

25 C6H~ 1 H HOCE13 eE~ I 2 CH

Q- 3 5 ~ R l l ~ R l ~ -CH3 ) 1 ~ 3 ~H2 CH

30 Q39(E'~5,E~53H) 1 ~ HOCR3 CE~¦ 2 C~3 Q- ~ 5 ' R6 ~ ~ 2 H HOCH3 OCE~3 CH
Q-5(E~,a6~ 2 H HOCH3 OCH3 CH
Q-~ (R5 ' =H) 2 E~ HOCH3 OCH3 CH
Q-14 (R5=H) 2 R HOCH3 OCE~3 CH

~a.~ t i nu ed Q ~ Y Z . p .
Q-16 (:R5 ~ P~6.H) 2 El H OCH3 ~CE~3 CH
Q 1 (a5 ~ %6 H) 2 H H O~H3 OCH3 N
Q-10(E~5~H) 2 E~ H OCH3 OCH3 N
Q-12 (E18-.H) 2 ~ H CH3 0~3 C?-18 tE~5-H. 1~6~CH3 ) 2 H H OCH3 OCH3 N
Q- 2 4 ( R5, E~6 ~ E~7 ~H ) 2 El H OCH3 OCH3 N
Q 27 (E~5 . R63EI) 2 1~ H O~H3 ~H3 N
$;!-33t~5,R6~H) 2 H H OCH3 3 N
Q-37~R5,R6~) 2 H H OCH3 OC~3 CH
Q-l(R5,R63H) 2 H H F OCW3 CH
Q-8 (R5 ' ~SCH3 ) 2 H H OCF2H OCH3 CH
Q-17(R5=H,R63CH3) 2 H H OCH2CH2F CH3 CH
Q-~(R5,R6=H) 2 H H OCE~2CH3 OCH3 N
Q-8 (R5 ' =SCH3 ) 2 H H CH2c~3 OCH3 N
Q- 8 ( R5 ' =CH3 ) 2 H H OC2H5 NHCH~ N

Q ( R$ SCH3 ) Z H H OCH3 CH~ CH

Q-lB(!~s=H~p~6=cH3) 2 H E~ CH3 CH ~ CE~
o ,CH
Q-8 (R5 ' 3CH3 3 2 H El OCH3 ~CH~
~H2 Q-l (R5 . R~EI3 2 H H OCH3 ~CH2 C6~15 2 H H OCH3 ~c~2 ~6E~5 2 H H OCEI3 ~ CH
35 Q-10 (R5=CH3) O H H OCH3 OCH3 N 185-188 3~ 3~r~

Table IIb ( H~ ) Q

Yl ~) n ~ 1 1 Yl m.P.~C
Q ( 5 ' 6 ~1 ) H H CH3 o Q-2(R5,R6=H) O R H CM3 o Q-3(R5,R6=H~ O H H CH3 o Q-4(R5,R,j=H) O H H CH3 o 15 Q-7(R5~R6~R7=H) O H H CH3 o Q-8 (R5 ' YSCH3 ) o H H CH3 o Q-8 (R5 ~ -~H3 ) o H H CH3 o 5;?-8 (R5 ~ ) o H H CH3 o Q-9 (R~;,=CH3 ) o H H CH3 o zO Q-l0(R5=CH3) 0 H H CH3 o Q-14 (R5=H) O H H CH3 o Q-16(R5,R6=H) O H H CH3 Q-l7(R~j"R~,=H) o H H CH3 o Q-lB (R5, R6=H) O H El CH3 o 25 Q~~l~R5~R6.R7=H) o H H CH3 o Q-22 (R5, R6 ~ R7=H) O H H 5H3 O
Q-Z4(R~,R6~R7=H) O H H CH3 o Q-27~R5,R6=H,n~=0) o H H CH3 o Q-30(R5,P~9,Rlo=H) O H E~ CH3 C) 30 Q-33(R5~a6=H) o H H CH3 o Q-~ (R5 ' =SCH3 3 O H H OCH3 o Q-1(E(5,R~ ) o H H 2~15 O
Q-9 (R5=CE13 ) O H H OCF2H o Q-8 (R5 ~ =CH3 ) O H H CH3 CH~
35 Q-EI(R5 =';CE~3) o H El OCH3 CH2 ~,~, D L~ r Table_ITb Continued -Q- n R Rl X
Q~ 5~R6=H) 1 H H CH3 o Q-2(R5.R6=H) 1 H H CH3 o Q-8(R5'=SCH3) 1 H H CH3 o Q-8(R5~=CH3) 1 H H CH3 o Q-14(R5=H) 1 H H CH3 o 10 Q 16(R5-R6 H) 1 H H CH3 o Q-17(R5,R6=H) 1 H H CH3 o Q-18(R5.R6=H) 1 H H OEl3 o Q-33(R5.R6~EI) 1 H H CH3 o Q-l(R~.R67H) 1 H C2H5 o lS Q-8(RS -CH3) 1 H H OCF2H
Q-8(R5'=SCH3) 1 H H OCH3 CH2 Q-8(R5~=CH3) 2 H H CH3 o Q-14(R5=H) 2 H H CH3 o Q-B(R5'=SCH3) 2 H OC2H5 o 20 Q ( 5~ 6 ) 2 H H CH3 o Table I I

Rl~507NliCON~
R N

~ n R R
Q 1 (R5 . P~6 H) 0 H H CH3 Q-2~R5.R6=H) O H H OCH3 Q- 3 ( R5, R6 =H ) O H H OC2H5 52-4(R5'~6=H) O H E~ CH3 Q-7(F~5,R6,R7=H) o H H C~3 Q-8 (R5 ~ =~CH3 ) o H H OCH3 Q-8 (R ' -CH ) O H H OCH3 Q-8 (P15 ' =E~) H H CH3 Q-9 (R5=CH3 ) O H H OCF2H
Q-lO(RS=CH3) 0 H H CH3 Q-14 (R5=H) O H H OCH3 Q-l~ (R5=H, ~6=CH3 ) O H H CH3 Q-17(R5=EI,R6=CH3) 0 H H OCF2E~
Q-lB(R~j,=H,R6=CH3) 0 H H OCH3 Q-21(R5,R6,R7=H~ O H H OCH3 Q-22(P(5,R6,R7=H) O H H CH3 Q-24(R5,R6,R~=H) O H H CE13 Q-27(R5.R~=H.Q'=O) O H H OCH3 Q-3(R5~R~,~Rlo=H~ O H H QCH3 3 0 S~ ~ 5, 6 H ) H H OCH3 Q-l(R5,R~ ) 1 H H CH3 Q ( 5 ' 6 ) 1 H H OCH3 Q ( 5 3 ) 1 H H OCH3 Q-8 (~5 ~ =SCH3 ~ 1 H H CEI3 Q-l~(R5=CH3) 1 H H OC2H5 ~,r;~ 7,~' 7~
Table I Iç _C~ontinued R 1 3~ 1 m . p . C
Q-14 (P~5-H) 1 R H OCH3 Q- 17 ( R5 -E~, R6 =CH3 ~ 1 Hl !E~ OCF2H
Q-?l~R5=H,R6=CH3~ 1 H H OCH3 Q-33(R5,R6=H) 1 H H OCH3 Q 8 ~R5 ' =CH3 ) 2 H H CH3 Q-27(R,R6=H,n'=0~ 2 H H OCEI3 Q-28(R5.R6=HOn'=1) 2 H H OCH3 Q ( 5 ' 6 ) 2 H H CH3 Q-4(R5,R6=H) 2 H 2E15 Table I Id P' 1 R ~

SL n R 1 ~1 Y2 Q ( 5 ' 6 ) H H CH3 CH3 Q-2 (R5, R~=H) O H H OCH3 CH3 Q-3 (R5 ~ ~6=H) O H 2 5 Q-4 (R5, R6=H) 0 H H CH3 CH3 Q-7(R5,R6,R7=H) 0 H H CH3 CH3 Q-~ ~R5 ~ =SCH3 ) o H H CH3 CH3 Q-8 (R5 ~ =CH3 ) O H H CH3 CH3 Q-B (~5 ' =H) H H CH3 CH3 S2 ( 5 3 ) El H OCF2H CH3 ;2-lO(R5=CH3) O H H CH3 CH3 Q-14 (R5=H) 0 H H CH3 C~3 Q-16(R5,R6=H~ O H H CH3 C~3 Q-17(~5,R6=H) O E~ H OCF2H CH3 Q-18(R5,R6=H) O El H OC2H5 CH3 Q-21(~5,R6,P~7=H) 0 E~ H CH3 CH3 Q-22(R5,R~,,R7=H~ o H H O~H3 H
Q-24(R5,R6,a7=E~) O H H OCF2H CH3 Q-27(R5,R62H,n'=o~ O H H CH3 CH3 Q-30(R5~EIg~Rlo=H) O H H C~3 c~3 3 O Q ( 5 t 6 ) H H s:~3 CH3 ;2 ( 5 ~ 6 ) 1 H H CH3 CH3 Q-2(R5,R~-H) 1 M H OCH3 CH3 Q-3(~5,R6=H) 1 H 2 5 Q-8 (R5 ' =SCH3 ) 1 H H CH3 ~H3 Q-8 (R5 ~ =CH3 ~ H3 CH3 Q-14 (P~5=H) 1 H H CH3 CH3 Table IId C~o~ntinued ~2_ n R 1 1 2 m. D. C
Q-l6~R5~H,R6~CH3) l H H CH3 CH3 Q-lg(R5=~R6=CH3) 2H5 C~13 Q-21(R5,R6,R7=H~ 1 H H ~H3 CH3 Q-Z7(R5,a6=H,n'=O) 1 H H CH3 CH3 Q-33(R5,R zH) l H H CH3 CH3 Q ( 5 ' 6 1 H H CH3 CH3 O-l(R5'R6=H) 2 H H CH3 CH3 Q-a (F~5 ' =SCH3 ) 2 H H CH3 CH3 Q-~ (R =CH ) 2 H H CH3 CH3 Q-l4 (R5=H) 2 H H OCH3 CH3 Q-33(R5,R6=H) 2 H H CH3 CH3 Table I Ie P~1~502NHcoN_<f ``N 3 Q n a Rl X2 Y3 m. p . C
10 Q 1 (R5 ,R6 H) H H CH3 CH3 Q-2(R5,R6=H) O H H OCH3 CH3 Q-3(R5,R6=H) O H C~13 C2H5 Q ( 5 ~ 6 H) H H ~H3 CH3 Q-7(R5,R6,R7=H) O H H CH3 CH3 15 Q ( 5 3 ) O H H CH3 CH2CF3 Q 3 (R5 H3 ~ H H CH3 C~2CF3 Q-a (R5 ' =H) O H H CH3 CH3 Q 9 (R5 H3 ) o H 3 CH3 Q-10 (R5=CH3 ) o H H CH3 CH3 Q-14 (R5=~) O H H CH3 ~2H5 Q-16(R5=H.R6=CH3) 0 H H CH3 CH3 Q-17(R5=H,R$=CH3) 0 H H OCH3 CH2CF3 Q-18 (R5=H. R6=CH3 ) O H 3 3 Q-21(R5'R6'~7=H) ~ ~ CH3 CH3 ~;?-22 (R5, R6 ~ R7=E~) O H o H3 C2H5 Q-24(R5~R6~R7=H) ~ 3 3 Q-27(R5,R6=H,r~ =O) O H H CH3 CH3 Q-30(R5,Rg,Rlo=H) O h H C~3 CH3 Q-33(R5,R6=H) O H H CH3 CH3 30 Q ~ 5 ' ~ ) 1 H H CH3 CH3 Q-2 (R5 ~RS=H) 1 H H H3 CH3 Q ( 5 3 ) 1 ~ H CH3 C2H5 Q-8 (R5 ' - SCH3 ) 1 H ll CH3 CH2CF3 Q ~ 5 3 ) 1 H 3 3 Q-10 (R5 CE~3 ) 1 H H CH3 CH3 5;?-14 (R5 H) 1 H H CH3 C2~5 ~ r, r~- ,r J, , ~

~10 ~ mled Q n R Rl X2 Y3 p. C
Q 16(P(5=H,R6=CH3)1 H H CH3 CH3 Q-27 (R5 ~ R6=EI)1 H E~ CH3 C~3 S?-33 (R5,R6=H) 1 H E~ CH3 CH3 Q-l(R5,R6=H) 2 H H CH3 c~3 Q ( 5 3 ) 2 H 3 3 ;2-14 (R5=H) 2 H H CH CH
1" 3 3 Q-18(R5=H,R6=CH3)2 H H OCH3 CH2CF3 2~

~0 1~1 ~.~

~ C~2 ) nQ OCH
5 ~N)150~NE~CON-CH2~N
El N~
~g3 ~ n p~ .P.C
Q-l(R5,R6~1) O H H CH3 Q-2(~5,~6~H) O M El ~H3 Q-3 (R5, ~6~H) o H H CH3 ~-4 ~R5, P~6.}1) o H H OCH3 15 Q-7(~5~R6~E~73H) O H H OCH3 Q-3IR5~ H3~ o H H CH3 Q-8 (R5 ' ~KSCE13 ) o H ~i ~CH3 Q-8(P(5'~H) 0 H H CH3 Q-9 (R ~CE~ ) O H H CH3 20 Q-lC~(R5'CH3) o H H OCH3 Q-14 tEa5DlH~ O El H OCH3 Q-l~R5DH,R6YCH3) 0 H H CH3 Q-17(R5~H,P~6~CH3) 0 H H CH3 Q-18(R5~EI,R6~CH3) 0 H H OCE~[3 25 ~-21(~,a6,1R7.~) 0 ~ EI CE~
Q~22~R~ 6,R~=H~ O H H OCH3 Q-24(F~5,E16.P~7=H) O lH ~ ~H3 Q-27(R~"R~ ) O E~ H CH~
Q-30(P~5~P~g~a~ ) E~ H OCH3 30 Q-33tp~5oR~i~H) o H H C~3 Q-3a ~ ,5.H) C H H CH3 Q-l tR5 ~ 1 lH H OCH3 Q-2 ~ 5, R~ -~H~ 1 H H CH3 Q~ sCH ) 1 H H ~H3 35 Q-~ (a5 ' SC'E13 ) 1 H ~ oc~3 .3 able I~I~ Con~inued Q n ~ Rl ~3 m. P . C
Q-10(R5=CH3) 1 El H CH3 Q-14 (R5=H) 1 H H CH3 Q-16(R5=H,R6=CH3~ 1 H 11 OCH3 Q-18(R5,H,R6=CH3) 1 H H OCH3 Q-27~R5,R6=H,n'Q0) 1 H H CH3 Q-3B(R5,R6=H~ 1 H EI OCH3 10 Q-l(R5,Rs=H) 2 R H OCH3 Q ( 5 H3 ) 2 H H OCH3 ez ~ J~3 Table II~

~f ~ CH2 ) nQ 2~

N S02NHCSN ~ ~ (Z
R N ~

Q n R ~l ~ Y Z ~p ~C
l0 Q-l~R5'R6=H~ H H OCH3 OCH3 CH
Q-l~R5,R6=H~13 OCH3 CH
Q ( 5~ 6 H)O H H OCH3 c~3 CH
Q-3(~5,R6=~)O H H OCH3 OCH3 CH
Q-4(R5,R~=H)0 H H OCH3 OC~3 CH
Q l(R5,R6 H)O H H CH3 OCH3 N
Q-8(R5'=CH3)O H O H3 CH3 CH
Q ( 5 ~3)OCH3 OCH3 CH
Q-lO(R5=CH3)O H H CH3 OCH3 CH
Q-l4(R5=H) H H OCH3 OCH3 CH
~O Q-l6~R5'R6=H~ H H OCH3 OCH3 CH
Q-l7(R5=H,R6=CH3) O H H OCH3 O~H3 CH
Q-2l(R5,R6,R7=H) O H H OCH3 OCH3 CH
Q-22(R5,R6,R7=H) O H H OCH3 OCH3 CH
Q-24(~5,R6,R7=H) O H H OCH3 OCH3 ~
25 Q-33(R5,R6=H)O H H OCH3 O~H3 CH
Q (R5 CH3)l H H OCH3 oc~3 CH
Q ( 5 3)l H H 3 H3 N
Q-8(R5'=CH3)O H H CH3 OCH3 N
Q-8(R5'=CH3)3 OCH3 Cff ~'1 Formulaeions U~e~ul formulation~ of the compound~ of For-mulae I and II can be prepared in conventional ways.
They include dusts, granule&, pellet6, ~olutions, su6pension6, wettable powders, emulsifiable concen-trates and the like. ~any of these may be applied directly. Sprayable formulation6 can be extended in suitable media and used at ~pray volume~ of from a few pints to several hundred gallon6 per~acre~ High strength composition~ are primarily used a~ interme-diates for further ~ormulation. The formulation~, broadly, contain about 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(~). ~ore specifically, they will con-tain these ingredients in the following approximate proportions:
Percent b~ Welg~
Active Inqredient Diluent(s~ Surfactant(s1 Weteable Powder~20-90 0-74 1-10 Oil Su~pen~ions 1-50 40-99 0-15 and Solutions (including Emulsifiable Concentrates) ~queous Suspension5-50 40-~4 1-20 Dusts 1-25 70-99 0-5 Granule6 and Pellets 1-95 5-99 0-15 High Streng~h 90-99 0-10 0-2 Compo6ition6 Lower or higher levels of active ingredient can, of cour6e, be pre~ent depending on the intended use and the physical propereies of the compound. Higher ratio6 of surfactant to active ingredient are some-~imes desirable, and are achieved by incorpora~ioninto the formulation or by tank mixing.

~ ypi~al ~oli~ fliluen~ are ~ ceibed in Watkln~
et al.~ "Handbook of In~ecticide Dust Dlluent6 and Cacrier~", 2n~. Ed., Dorland Book6, Caldwell, NJ. The ~ore ab60rptive diluents are prefecred for wettable powder6 and the denser one~ ~o~ dusts. Typical liquid diluents and 601ventfi are de~cribed in Mar6den, "Sol-vent6 Guide", 2nd. Ed., Inter~cience, New Yo~k, 1950.
Solubility under 0.1% is preferred for ~u~pen~ion concentratefi: 601ution concentrate~ are preferably 6table again~t p~a6e separation at 0C. "McCutcheon's Detergent~ and Emul6ifier~ Annual", Allured Publ.
Corp., Ridgewood, NJ, as well as Si6ely and Wood, "Encyclopedia of Surface Active Agent~", Che~ical Publ. Co., Inc., New York, 1964, li~t ~ur~actant~ and reco~mended u~e~. All formulation~ can contain minor amount~ of additives to reduce foam, corrozion, micro-biological growth, etc. Preferably, ingredients 6hould be approved by the appropriate governmental bodies for the use intended.
The methods of making such compo~i~ions are well known. Solution~ are prepared by simply mixing the ingredient~. Fine 601id ~ompo~ition6 are made by blending and, usually, grinding a~ in a hammer or fluid en~rgy mill. Suspen~ions are prepared by wet ~illing (fiee, ~or example, Littler, U.S. Patent 3,060,084~. Granules and pellet~ may be made by 6praying the active ma~erial upon preformed granular carrier~ or by agglomeration technique6. (6ee J. ~.
~rowning, "Agglomeration", Chemical En~in e~
December 4, 1967, pp 1~7ff. and "Perry'~ Che~ical ~ngineer'6 Handbook", 4th Ed., McGraw-Hill, NY, 19~3, ~P ~-5g~

~ r.~ r~' ~361 Exam~le_6 ettable Powder N-~(4,6-dimethoxypyrimidin-2-yl)aminocacbonyl]-2-(lH-1~2,4-tLiazol-l-yl)-3-pyridine6ulfonamide 80 sodium alkylnaphthalene~ulfonate 2 sodium lignin6ulfonate 2~
synthetic amorphous silica 3%
kaolinite 13%
The ingredient~ are thoroughly blended and hammer-milled or air-milledl to produce particles averaging below 20 micron~ in diamete~. The product is reblended before packaging.
Example 7 Oil ~usPen6ion N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonYl]-2-(lH-1,2,4-triazol-1-yl)-3-pyridinesulfona~ide 35%
blend of polyalcohol carboxylic e6ters and oil soluble petroleum ~ulfonatefi 6%
Xylene 59%
The ingredient6 are combined and ground together in a ~and mill to produce particles e~entially all below 3 microns. The product can be used directly, extended ~ith oil~, or emulsified in water.
Example 8 Oil Suspension N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl~ (lH-1,2,4-triazol-1-yl)-3-pyridine~ulfona~ide 25~
polyoxyethylene ~orbitol hexaoleate 53 highly aliphatic hydrocarbon oil 70%
The ingredient~ are ground together in a ~and mill un~il the 601id particle~ have been reduced ~o unde~ about 5 ~icrons. The re~ulting thick suspen~ion may be applied directly, but preferably after being extended ~ith oil~ or emul~ified in water.

~6 ~ r ~ `3 r~

~ 7 xamp.le 9 Solution N-[(4,6-dimethoxypyri~idin-2-yl)aminocarbonyl]-2-(lH-1,2,4-triazol-l-yl)-~-pyridine6ulfonamide 5~
dimethylfor~amide 95%
The ingredients are combined and ~tirred to produce a ~olu~ion which can be u~ed for low volume application6.
ExamPle 10 Emul~ifiable Concentrate N-[~4,6-dimethoxypyrimidin.-2-yl~aminocarbonyl]-2-(lH-1,2,4-tria~ol-1-yl)-3-pyridinesulfonamide 5.0%
blend of oil soluble sulfonAtes and polyoxyethylene ethers 4.0%
N-methyl pyrrolidone ~5.5%
xylene 45-5%
The active ingredient6 are combined and ~tirred until dissolved. A fine screen filter is included in packaqing operation to insure the ab6ence of any extraneous undissolved material in the product.
Exam~le 11 Aqueous Suspen~niorl ~-[(4,6-dimethoxypyri~idin-2-yl)aminocarbonyl]-2-(lH-1,2,4-tria201-l-yl)-3-pyridine6ulfonamide 50.0%
dodecylp~enol polyethylene glycol ether 0.5%
crude calciu~ ligninsulfonate 5.0%
xanthan gum thickener 0.2~
paraformaldehyde 0.2%
water 44.1 The ingredien~ are ground toge~her in a 6and ball or roller mill to produce particle6 essen~ially all under five microns in ~ize.

/ ~ t - r ,~ ~3 r~ e-Exa~le 12 Du~t N-~4.6~dimethoxypyrimidin-2-yl)am~nocarbonyl]-2-(lH-1,2~4-tciazol-1-yl)-3-pyridinesul~onamide (active ingredient) 20~
attapulgite 10%
talc 70S
The ingredient i~ ble!nded with attapulgite and then passed through a hammer-mill to produce parti~les substantially all below 200 microns. The gr~und concentrate i6 then blendedl with powdered talc until homogeneous.
Example 13 Dust lS wettable powder of Example 6 5%
pyrophyllite (powder) 95%
The wettable powder and the pyrophyllite diluent are thoroughly blended and then packaged. The product i8 suitable for use as a du6t.
ExamPle 14 Granule wettable powder of Example 6 84%
~ugar 16%
The ingredients are blended i~ a rotating or fluid bed mixer and water ~prayed on to acco~plish granulation. ~hen mo~ of the material ha6 reached the de~ired range of 1.0 to 0.52 mm. (U.S.S. ~18 to 40 ~ieves), the granule~ are removed, dried, and 6creened. Over~ize material i~ crushed to produce additional material in the desired range.

~8 ~`1 r~ f ~ D,~ r~
as ExamPle 15 Granule wettable powder of Example 6 10%
attapulgite g~anules (U.S.S. #20-40: O.B4-0.42 mm) 90 A ~lurry of wettable powder containing 50%
601id6 is 6praysd on the su~face of attapulgite granule~ in a double-cone blender. The granules are dried and packaged.
Example 16 Extruded Pellet N-[(4,~-dimethoxypyrimidin-2-yl)aminoca~bonyl]--2-(lH-1,2,4-triazol-1-yl)-3-pyridine~ulfonamide 25~
anhydrous sodium sulfate 10%
crude calcium ligninsulfonate 5~
~odium alkylnaphthalenesulfonate 1%
calcium/magnesium bentonite 59%
The in~Ledient~ are blended, hammer-milled and then moistened with water. The mixture is extruded as cylinders about 3 mm diameter which are cut ~o produce pellets about 3 mm long. These may be used directly after dlying, or the d~ied pellets may be crushed to pas& a U.S.S. ~20 sieve (0.84 mm opening6). The granules held on a U.S.5. #40 fiieve (0.42 ~m openings) may be packaged for u~e and ~he fines recycled.
ExamPle 17 Hiqh Strenqth Concentrate N-~(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-~-(lH-1,204-triazol-l-yl)-3-pylidinesulfonamide 98.5%
gilica aerogel 0.5%
synthetic amorphous fine silica 1.0%
The ingr~dient~ are blended and ground in ~
hammer-mill to produce a high strength concen~rate essen~ially all pas6ing a U.S.S. ~50 sieve (0.3 mm opening63. This material may then be formula~ed in a varie~y of way6.

--~ f~ 3""

Utilit~
Te~t re6ulta indicate that the compounds o~ the present invention are highly active preemergent or postemecgent herbicide6 or plant growth regulant6.
~any of them have utility for broad-spectrum pre- and or post-emergence weed control in area6 where complete con~rol of all vegetation i~ desired, ~uch a~ around fuel storage tanks, ammunition depo~, industrial stoIage areas, pa~king lot~, drive-in theaters, around billboards, highway and railroad structures.
Some of the compound~ have utility for selective weed control in crops such as rice, wheat, barley and cocn.
Alternatively, the zubject compound~ are useful to modify plant grow~h.
The rates o~ application ~or the compounds of the invention are de~ermined by a number of factor6, including ~heir use as plant growth modifiers or as herbicide~, the crop species involved, the types of weed6 to be controlled, weather and climate, formu-lation6 selected, mode of appllcation, amount of foliage present, etc. In general term~, the subject compound~ should be applied a~ levels of around 0.05 to 10 kg/ha, the lower rate~ being ~ugge~ted for u~e on lighter 60ils and/or those having a low organic matter content, for plant growth modification or for situations where only shor~-term persi6tence is requiled .
The compounds of ~he invention may be used in combination wi~h any other commercial herbicide, exam-ple6 of which are tho~e of ~he triazine, triazole,uracil, urea, amide, diphenylether, carbamate and bipyridylium type6.
The herbicidal p~operties of the sub~ect com-pounds were discovered in a number of greenhouse te~ts. The test procedure6 and re~ults follow.

Com~ound 8 Compound 1 [~ SOzNHCONH~

N~

Compound 2 OCH
N
~, S02NHCONH~O~
15~ N ~ N'^~N CH3 N

Compound 3 N -t J
N

2 i~

Test A
Seeds of crabgrass (~g~__ria ~pp-), barnyard-gra~s (Echinochloa g~y~q~ , wild oat~ (Avena fatua), sicklepod ~Cassia obtusifolia), morningglory (Ipomoea 8pp. ), cocklebur (Xanthium Pen~Ylvanicum), sorghum, corn, soybean, sugar beet, cotton, rice, wheat, and purple nutsedge (Cyperus rotundu~) tuber~
were planted and treated pceemergence with the test chemical6 dis~olved in a non-phytotoxic solvent. At the game time, these crop and weed ~pecies were ~eated with a soil/foilage application. At the time of treatment, the plants ranged in height from 2 to 18 cm. Treated plant~ and conl:rol6 were maintained in a greenhou~e for sixteen day&D after which all ~pecies weIe compared to control~ and visually rated for re6ponse to tLeatment. The rating~, sum~arized in Table A, are bafied on a numerical scale extending from 0 = no injury, to 10 = complete kill. The accompany-ing descLiptive 6ymbol~ have the ~ollowing meanings:
C = chlorosi~necrosi~;
B - burn:
D = defoliation;
E = emergence inhibition;
G = grow~h retardation, ~ = formative effect:
U = unusual pigmentation;
= axillary stimulation;
S = albini~m; and 6Y = abscised buds or flowe~s~

Table A

Compound 1 Compound 2 ~ate g/ha 2000 400 2000 400 POSTEMERGENCE
Cotton 5C,9G 4C,9G 4C,9G 3C,9H
Sorghum 3C,8H 2C,2G 3C,6G 3C
Corn 3C,8H O 2C,6H O
Soybean 3C,8H 3C,8G 3C,8G 2C,8G
Wheat 5G O 5G 2G
Wild Oats O 0 5G O
Rice 2C,9G 3G 4C,BG 3C,5G
~arnyardgra~6 3C,9H 2G 4C,BH O
Morningglory3C,8H3C,~H 3C,8H 3C,7H
Cocklebu~ 5C,9H 4C,8H 3C,9~ 4C,9 Sicklepod 4C,8H 3C,7G 3C,8H 4C,5G
Nut~edge 2C,9G 2C,9G 3C,9G 3c~aG
Sugar beet 9C 5C,9G 9C 9H
PREEMERGENCE
Cotton 9G 8G 9G 7G
Sorghum 3C,9G 3C,5G 3C,8H 2C,5G
Corn 2C,9G 3C,7H 3C,9H 3C,7G
So~bean 3C,7G 3C,6G 4C,8H 3C,6H
Wheat 2G O 2C,7G 3G
~ild ~ats 0 0 3C,8G O
Rice 9H 5G 4C,8H 2C,5G
Barnyardgrass 8H 3C,6H 3C,8H O
Morningglory9G 9G 9G 3C,8H
Cocklebur 9H 7H - 3C,8H
Sicklepod 8G 4C,8G 4C,9G 3C,5G
25 Nutsedge lOE 5G 10~ 0 Sugar beet4C,9G 5C,9G 5C,9G 3C,9G

9g Table A ~ontinu d~

Compound 3 5 Rate g/ha 2000 ~oo POSTEMERGENCE
Cotto~ 3C,9H 3C,5H
Sorghu~ o o Corn 0 o Soybean o o 10 ~heat 0 0 Wild Oats o ~ice 3C,SG o Barnyardgrass 0 o Morningglory o 0 Cocklebur 0 0 Sicklepod o 0 15 Nut~edge 0 0 Sugar beet 0 o PREEMERGENCE
Cotton 2G o Sorghum o 0 Corn 2G 0 5Oybean 2C 0 20 Wheat o o Wild Oats o o Rice 2C 0 Barnyardgras~ 0 o Morningglory 2C 0 Cocklebur o o Sicklepod 2C 0 25 Nutsedge 0 0 Sugar beet 5G O

Claims

WHAT IS CLAIMED IS:

1. A compound of the formula I or II

I II

wherein R is H or CH3;
R1 is H, Cl, Br, SCH3 or CH3;
n is 0, 1 or 2;
W is O or S;
Q is a saturated 5- or 6-membered ring containing one heteroatom selected from O, S, or N, or an unsaturated 5- or 6-membered ring containing 1 to 3 heteroatoms selected from 0-1 S, 0-1 O or 0-3 N and when Q is an unsaturated 5- or 6-membered ring, it may optionally be substituted by one or more groups selected from C1-C4 alkyl, halogen, C3-C4 alkenyl C1-C3 alkoxy, C1-C3 alkylthio, C3-C4 alkenyl-thio, C1-C2 haloalkoxy or C1-C2 haloa1kylthio;

X is CH3, OCH3, OCH2CH3, Cl, F, Br, I, OCF2H, CH2F, OCH2CH2F, OCH2CHF2, OCH2CF3 or CF3;
Y is H, C1-C2 alkyl, OCH3, OC2H5, CH2OCH3, NHCH3, N(OCH3)CH3, N(CH3)2, CF3, SCH3, OCH2CH=CH2, OCH2C?CH, CH2OCH2CH3, OCH2CH2OCH3, CH2SCH3, , , OCF2H, SCF2H
or cyclopropyl;
m is 2 or 3;
L1 and L2 are independently O or S;
R2 is H or CH3;
R3 and R4 are independently C1-C2 alkyl;
Z is CH or N;
Y1 is O or CH2;
X1 is CH3, OCH3, OC2H5 or OCF2H;
Y2 is H or CH3;
X2 is OCH3 SCH3 or CH3;
Y3 is CH3, C2H5 or CH2CF3; and X3 is CH3 or OCH3;
provided that a) when X is Cl, F, Br or I, then Z is CH and Y
is OCH3, OC2H5, N(OCH3)CH3, NHCH3, N(CH3)2 NH2 OR OCF2H;
b) when Y is cyclopropyl, X is other than Cl, F, Br or I;
c) when Q is 1H-1,2,4-triazol-1-yl, then Z is CH;
d) when X or Y is OCF2H, then Z is CH;

e) when Q is a saturated 5- or 6-membered ring containing one nitrogen atom, it is bonded to the pyridine ring through carbon; and f) when W is S, then R is H, A is A-1 and Y is CH3, OCH3, OC2H5, CH2OCH3, C2H5, CF3, SCH3, OCH2CH=CH2, OCH2C?CH, OCH2CH2OCH3, CH(OCH3)2 or ;

and their agriculturally suitable salts.

2. A compound of Claim 1 selected from Formulae I or II wherein R is H;
W is O;
Q is selected from the group consisting of n' is 0 or 1;
R5, R6 and R7 are independently H or CH3;
R? is H, CH3, C2H5, C1-C3 alkylthio, SCH2CH=CH2, SCF2H, OCH3 or OCH2CH3;
R8 is H or Cl;
R9 and R10 are independently H, CH3 or OCH3;
R11 and R12 are independently CH3 or OCH3;
W' is O, S or NR13; and R13 is H, C1-C3 alkyl or CH2CH=CH2;

3. A compound of Claim 2 wherein A is A-1;
R1 is J; n' is O; and Q is selected from the group consisting of Q-1, Q-2, Q-3, Q-4, Q-7, Q-8, Q-9, Q-10, Q-11, Q-14, Q-16, Q-17, Q-18, Q-21, Q-22, Q-24, Q-27, Q-30, Q-33, Q-37, and Q38.

4. A compound of Claim 3 wherin X is CH3, OCH3, OCH2CH3 or Cl and Y is CH3, CH2CH3, OCH3, CH(OCH3)2 or CH2OCH3.

5. A compound of Claim 4 where n is O.

6. A compound of Claim 5 where Y is CH3, CH2CH3, OCH3 or OCF2H

7. A compound of Claim 6 of Formula I.
8. A compound of Claim 6 of Formula II.
9. The compound of Claim 1 which is N-[(4.6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(1H-1,2,44-triazol-1-yl)-3-pyridinesulfonamide.
10. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected, an effective amount of a compound of Claim 1.
11. A method for controlling the growth of undesired vegetation which comprises applying the locus to be protected an effective amount of a compound of Claim 2.
12. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 3.
13. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected, an effective amount of a compound of Claim 4.
14. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 5.
15. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 6.

16. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected, an effective amount of a compound of Claim 7.
17. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of

Claim 8.