JPS6233173A - Herbicidal pyrazolesulfonamides - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to herbicidally active pyrazole sulfonamides with certain attached heterocycles, agriculturally suitable compositions thereof, as well as herbicides and/or plant growth regulators. and their use as agents.

Under the most common circumstances, undesirable plant adjustments
It is desirable to allow the growth of useful crops such as cotton, rice, corn, wheat and soybeans.

Uncontrolled weed growth in such useful crops results in considerable damage, reduced profits for farmers, and increased prices for consumers. In other situations, herbicides that control the growth of all plants are desired. Examples of locations where complete destruction of all plants is desired are fuel storage tanks, ammunition depots and industrial storage locations. There are many commercially available products for these purposes, and research continues into more effective, less expensive, and environmentally safe products.

European Patent Application (EP-A) 95.925 (1
(published on December 7, 1983), the group adjacent to the sulfonamide moiety is HXC, -C, alkyl, F, ClX
Br, NO2, OR,, Co2R23,5(0)n
Disclosed are herbicidal pyrazole sulfonamides such as those selected from R,4 or 802NR, R,o.

European Patent Application No. 87,780 (published on September 7, 1983) describes the general formula [wherein A is H, C1-C8 alkyl or optionally substituted phenyl, and B and C are independently H1 halogen, NO2, C, -C
8 alkyl, COR, etc., and D is H or C, -C, alkyl].

South African Patent Application No. 83/3850, published on November 28, 1983, describes the general formula [wherein R1 is H or C, -C, alkyl, and and 2 or 3
is an unsubstituted or substituted 5-membered heterocyclic group containing identical or different heteroatoms.

Unexamined Japanese Patent Application No. 9.013.778, published November 24, 9984, describes herbicidal pyrazole sulfonamides having halo, alkyl and alkoxycarbonyl substituents.

European Patent Application No. 83,975 (July 20, 1983
Japanese Publication No. 85.476 (1) and European Patent Application No. 85.476 (1)
(published on August 10, 1983) is a herbicidal benzenesulfonamide compound of the general formula (wherein Q is one of various 5- and 6-membered saturated or unsaturated heterocyclic rings). Disclosed.

The present invention provides novel compounds of formula I, suitable agricultural compositions containing them, and general and/or selective pre- and/or post-emergent herbicides and/or plant growth control agents. It relates to their use as modulators.

LSO, NHCN-A 1. 8.1 o, l
- unsaturated 5- or 6-membered rings containing 1-3 heteroatoms selected from 3 N, and combinations thereof, and Q is optionally C, -C4 alkyl, C, -C, no\roalkyl, mercapto, be/
Dilthio, halogen, C, -04alcoquine, C, -C
.

Alkylthio, C3-C4 alkenyl, C3-C, fulkenylthio, C1-C4 alkynyl-yr, cs-C
<Haloalkenylthio, C3-c4 alkenyloxy,
C, (:', /10 alkoxy, C1-C2 haloalkylthio, C2-C, cyanoalkylthio, 'c3-c,
Alkoxycarbonylalkylthio, C2-c.

Alkoxyalkylthio may also be substituted with one or more groups selected from CsCsacetylalkylthio, W is O or S, R is H or CH3, R1 is H,, C1 -C5 alkyl, C, -C, \roalkyl or optionally C1,, NO2, CH3 or O
phenyl optionally substituted with CH, R121 is HXCl or CH3, RI4 is H,
C1-C4 alkyl, FXCl.

B", NO□, C, -C, haloalkylthio, C3-C
, alkenyl, C3-C, alkynyl, Co2R,7,
C1-C, alkylthio, C, -CS alkylsulfinyl, C, -C, alkylsulfonyl or SO, NR
'R ■ Thea, )), R115 and J are independently H,
C, -C4 alkyl, C2-04 alkoxyalkyl,
C1-C5 haloalkylthio, C1-C31\roalcoquine, C, -C, alkoxy, C, -C.

Alkylthio, C1-C5 alkylsulfony2, F, C
I, B rXCO2RI? 't or 5o2NR'RII
, R■ and Brl are independently e, -03 alkyl, R1□ is Cl-03 alkyl, CH, CH=CH2, C
H2C=CH, CH, CH, CI or CH2CH.

OCH, A is H, C, -C, alkyl, C1-C, alkoxy,
C, -C4 haloalkoxy, C, -C, haloalkyl,
C, -C, haloalkylthio, C, -C4 alkylthio, 110ge/, C2-C5 alkoxyalkyl, C2-
C, alkoxyalkoxy, amine, C, -03alkylamino or di(C1''3alkyl)amino, Y is HXC, -04alkyl, c, -c4alkoxy,
C, -C, haloalkoxy, C, -C.

Haloalkylthio, C0-C, alkylthio, C, -C
, alkoxyalkyl, C, -C, alkoxyalkoxy, amino, C, -C, alkylamino, di(C1"3
alkyl)amino, C3-C4 alkenyloxy, C,
-04 alkynyloxy, C2-C, ayureki, rethioalkyl, C2-C5 alkylsulfinyl alkyl,
C2-C, alkylsulfonylalkyl, c, -'c4
Haloalkyl, C1-C, nocroalkyl, C, -C4
Alkyni N(OCH,)CH3, m is 2 or 3, Ll and R2 are independently 0 or S, and R8 is H
or CHl, R2 and R1 are independently C, -C, alkyl, Z is CHt or N, Y is O or CH2, X is CH,, OCH3, QC, H , or 0CF2H
, Y2 is H or CH, X2 is CH4, C2H5 or CH, CF, and ¥
3 is 0CH4, 0C2H3, SCH3, 5C2F■3.
0CF2HXSCF2HXCH1 or C2H, X3 is CH8 or OCH, X, i CH8, OCH,, QC2H,, CH2OC
H3 or C1 and Y is CH3, OCH, or QC2) (with the proviso that]) when X is C1, BrXF or 1, Z is CH and Y is OCH,,QC ,H,,N(QC)(3)CH3,NH
CH3, N(CH3)2, NH2 or OCF2H; 2) When X or Y is OCF2H, Z is CH
3) When W is S, R is H and A is A-1
and Y is CH,,OCH3,0C2H3,C
H20CH1, C2H5, CFi, 5CH1, 0CH2
CH=CH2, OCH, C=CHX0CH, CH20C
H1,4) When the total number of carbons in X and Y is greater than 4, the total number of carbons in Q and R4, R23, R+st or R26 is 10 or less, and 5) L is L-5, I, -6 or L-7, Q must be attached to the pyrazole ring via a carbon atom] and commercially suitable salts thereof.

In the above definitions, the term "alkyl" used alone or in compound words such as "alkylthio" or "haloalkyl" refers to straight-chain or branched alkyl, e.g. methyl, ethyl, n-propyl. , isopropyl or various butyl, pentyl and hequinyl isomers.

Alkoxy is an isomer such as methoxy, ethoxy, n
- is meant to include propoxy, impropoxy and butoxy isomers.

Alkenyl means straight-chain or branched alkenes, such as 1-propenyl, 2-propenyl, 3-propenyl and the various butenyl isomers.

Alkynyl refers to straight or branched alkynes, such as methynyl, 1-propynyl, 2-7''ropynyl and the various butynyl isomers.

Alkoxycarbonyl means methquincarbonyl or ethoxycarbonyl.

Alkylsulfonyl refers to methylsulfonyl, ethylsulfonyl and various propylsulfonyl isomers.

Alkylthio, alkylsulfinyl, alkylamino, etc. are defined in a similar manner.

Cycloalkyl means, for example, cyclopropyl, cyclobutyl and cyclopentyl.

The term "halogen" alone or in a compound term such as "haloalkyl" refers to fluorine, chlorine, bromine or iodine.

The total number of carbon atoms in a substituent is indicated by the prefix CI-Cj, where i and j are numbers from 1 to 6. for example,
C2C5 alkoxyalkylthio is 5CH20CH1 to 5CH2QC,H, or S CHt CH2CH2
It is meant to include up to CH, OCH3 and various structural isomers included therein.

C2-C4 cyanoalkylthio is 5CH2CN.

SCH, CH2CN, 5CH(CH3)CN,, SCH
, CH2CH2CN and various 04 isomers.

The term C8-05 acetylalkylthio is SCH,C
(0)CH, to 5CH2CH2CH, C(0)CH
, and various structural isomers included therein.

Preferred for reasons of relative ease of synthesis and/or relatively high herbicidal efficacy are: 1) Q is CH3R1゜Q-22Q-23Q-24 and Ro and R9 are independently is H or CH3, and R7
is H, CH3 or CI, and R8 is HXSH, Cl-13, CH2, CH3, S(C
, -C4 alkyl), 5(C3-C,alkenyl), 5(C5-C4 alkynyl), OCH3, OCH, optionally substituted with 1 or 2 halogen atoms
S(C,-
C, alkyl), and Rlo and RlI are independently HXCH3 or OCH
.

, R1□ and R, U are independently CH3 or OCH3, R'+a is H, C, -C, alkyl or C, -C3 alkylthio, and R19 is C, -C, alkyl or (Ji 2CH=C
'H2, but as a condition, when L is L-5, L-6 or L-7, Q is Q-25, Q-26, Q-27, Q, -
28, compounds of 2I that are not Q-41, Q-42, Q-43 or Q-44.

2) Compounds according to preferred item 1, wherein R is H and W is 0.

3) R1 is C, -C, alkyl and Y is CH,,O
CR3, CH2OCH3, NHCH3, CH2CH3,
C=CH1C==CCH,, CH(OCH,)2, CH
(CH,)2 or cyclopropyl, and R8 is HX
SH, CH,,5CH3-r tide, QCH, terror
Rh, H, CHs, C2H5, Co, CH3, C
o, C, H,, F, ClXBr, 802CH1,5
o2C2H,,0CF2Ht Taha5O2N(CH3)
2tea)), and R, and R16 are independently H, CH,, C, I(3,
CO2CH3, co2C2H3, F, CI, B r ,
80. Compounds of preferred item 2 which are CHs, 5O2C2H6,0CF2HX or 5o2N(CH,)2.

4) X is CH3, OCH3, oC2H6, C1, Br1
Compounds according to preferred item 3, wherein f and nee are 0CF2H.

5) Compounds according to preferred item 4, wherein A is A-1, L is L-1, and Q is Q-1.

6) Compounds according to preferred item 4, wherein A is A-1, L is L-1, and Q is Q-2.

7) Compounds of preferred item 4, wherein A is A-1, L is L-1, and Q is Q-3.

8) Compounds according to preferred item 4, wherein A is A-1, L is L-t, and Q is Q-4.

9) Compounds according to preferred item 4, wherein A is A-1, L is L-1, and Q is Q-s.

10) A is A-1, L is L-1, and Q
Compounds according to preferred item 4, wherein is Q-6.

11) A is A-1, L is L-1, and Q
Compounds according to preferred item 4, wherein is Q-7.

12) A is A-1, L is L-1, and Q
Compounds according to preferred item 4, wherein is Q-8.

13) A is A-1, L is L-1, and Q
Compounds according to preferred item 4, wherein is Q-9.

]4) A is A-1, L is L=1, and Q
Compounds according to preferred item 4, wherein is Q-10.

]5) A is A-1, L is L-1, and Q
Compounds according to preferred item 4, wherein is Q-11.

16) A is A-1, L is L-1, and Q
Compounds according to preferred item 4, wherein is Q-12.

17) A is A-1, L is L-1, and Q
Compounds according to preferred item 4, wherein is Q-13.

18) A is A-1, L is L-1, and Q
Preferred ring 4 compounds, wherein is Q-14.

19) A is A-1, L is L-1, and Q
Preferred ring 4 compounds, wherein is Q-15.

20) A is A-1, L is L-1, and Q
Preferred ring 4 compounds are -16.

21) A is A-1, L is L-1, and Q
Preferred ring 4 compounds, wherein is Q-17.

22) A is A-1, L is L-1, and Q
Preferred ring 4 compounds, wherein is Q-18.

23) A is A-1, L is L-1, and Q
Preferred ring 4 compounds, wherein is Q-19.

24) Preferred Ring 4 compounds, wherein A is A=1, L is I, -1, and Q is Q-20.

25) A is A-1, L is L-1, and Q
Preferred ring 4 compounds, wherein is Q-21.

26) Preferred ring 4 compounds, wherein A is A-1, L is L-1, and 2 and Q is Q-22.

27) A is A-1, L is L-1, and Q
Preferred ring 4 compounds, wherein is Q-23.

28) A is A-1, L is L-1, and Q
Preferred ring 4 compounds, wherein is Q-24.

29) A is A-1, L is L-1, and Q
Preferred ring 4 compounds, wherein is Q-25.

30) A is A-1, L is L-1, and Q
Preferred ring 4 compounds, wherein is Q-26.

31) A is A-1, L is L-1, and Q
Preferred ring 4 compounds, wherein is Q-27.

32) A is A-1, L is L-1, and Q
Preferred ring 4 compounds, wherein is Q-28.

33) A is A-1, L is L-1, and Q
Preferred ring 4 compounds, wherein is Q-29.

34) A is A-1, L is L-1, and Q
Preferred ring 4 compounds, wherein is Q-30.

35) Preferred ring 4 compounds, wherein A is A-1, L is IL-1, and Q is Q-31.

36) Preferred ring 4 compounds, wherein A is A-1, L is L-1, and Q is Q-32.

37) A is A-1, L is L-1, and Q
Preferred ring 4 compounds, wherein is Q-33.

38) A is A-1, L is L-1, and Q
Preferred ring 4 compounds, wherein is Q-34.

39) A is A-1, L is L-1, and Q
Preferred ring 4 compounds are -35.

40) A is A-1, L is L-1, and Q
Preferred Ring 4 compounds, wherein is Q-36.

41) A is A-1, L is L-1, and Q
Preferred Ring 4 compounds, wherein is Q-37.

42) A is A-1, L is L-1, and Q
Preferred ring 4 compounds, wherein is Q-38.

43) A is A-1, L is L-1, and Q
Preferred ring 4 compounds, wherein is Q-39.

44) Eight is A-1, L is L-1, and Q
Preferred Ring 4 compounds, wherein is Q-40.

45) A is A-i, L is L-1, and Q
Preferred ring 4 compounds, wherein is Q-41.

46) Preferred Ring 4 compounds, wherein A is A-1, L is I, -1, and Q is Q-42.

47) A is A-1, L is L-1, and Q
Preferred Ring 4 compounds, wherein is Q-43.

48) A is A-1, L is L-1, and Q
Preferred Ring 4 compounds, wherein is Q-44.

49) A is A-1, L is L-1, and Q
Preferred Ring 4 compounds, wherein is Q-45.

50) A is A-1, L is L-1, and Q
Preferred ring 4 compounds, wherein is Q-46.

51) A is A-1, L is L-1, and Q
Preferred Ring 4 compounds, wherein is Q-47.

52) A is A-1, L is L-1, and Q
Preferred Ring 4 compounds, wherein is Q-48.

53) Enter is A-1, L is L-2, and Q
Preferred ring 4 compounds, wherein is Q-1.

54) A is A-1, L is L-2, and Q
Preferred ring 4 compounds, wherein is Q-2.

55) A is A-1, L is L-2, and Q
is Q-3, preferred ring 4 compounds 56) A is A-
1, L is L-2, and L2 and Q are Q-4.

57) A is A-1, L is L-2, and Q
Preferred ring 4 compounds, wherein is Q-5.

58) A is A-1, L is L-2, and Q
Preferred ring 4 compounds, wherein is Q-6.

59) A is A-1, L is L-2, and Q
Preferred ring 4 compounds, wherein is Q-7.

F+Q) Preferred Ring 4 compounds, wherein A is A-1, L is I, -2 and Q is Q-8.

61) A is A-1, L is L-2, and Q
Preferred ring 4 compounds, wherein is Q-9.

62) A is A-1, L is L-2, and Q
Preferred ring 4 compounds, wherein is Q-10.

63) N is A-1, L is L-2, and Q
Preferred ring 4 compounds are Q-11.

64) A is A-1, L is L-2, and Q
Preferred ring 4 compounds, wherein is Q-12.

65) A is A-1, L is L-2, and Q
Preferred ring 4 compounds, wherein is Q-13.

66) A is A-1, L is L-2, and Q
Preferred ring 4 compounds, wherein is Q-14.

67) A is A-1, L is L-2, and Q
is Q-15, preferred ring 49 compounds.

68) A is A-1, L is L-2, and Q
Preferred ring 4 compounds, wherein is Q-16.

69) Preferred ring 4 compounds, wherein A is 8-, L is L-2, and Q is Q-17.

70) A is A-1, L is L-2, and Q
Preferred ring 4 compounds, wherein is Q-18.

71) A is A-1, L is L-2, and Q
Preferred ring 4 compounds, wherein is Q-19.

72) A is A-1, L is L-2, and Q
Preferred ring 4 compounds, wherein is Q-20.

73) A is A-1, L is L-2, and Q
Preferred ring 4 compounds, wherein is Q-21.

74) A is A-1, L is L-2, and Q
Preferred ring 4 compounds, wherein is Q-22.

75) A is A-1, L is L-2, and Q
Preferred ring 4 compounds, wherein is Q-23.

76) A is A-1, L is L-2, and Q
Preferred ring 4 compounds, wherein is Q-24.

77) A is A-1, L is L-2, and Q
Preferred ring 4 compounds, wherein is Q-25.

78) A is A-1, L is L-2, and Q
Preferred ring 4 compounds, wherein is Q-26.

79) A is A-1, L is L-2, and Q
Preferred ring 4 compounds, wherein is Q-27.

80) A is A-1, L is L-2, and Q
Preferred ring 4 compounds, wherein is Q-28.

81) A is A-1, L is L-2, and Q
Preferred ring 4 compounds, wherein is Q-29.

82) A is A-1, L is L-2, and Q
Preferred ring 4 compounds, wherein is Q-30.

83) A is A-1, L is L-2, and Q
Preferred ring 4 compounds, wherein is Q-31.

84) A is A-1, L is L-2, and Q
Preferred ring 4 compounds, wherein is Q-32.

85) A is A-1, L is L-2, and Q
Preferred ring 4 compounds, wherein is Q-33.

86) A is A-], L is L-2, and Q
Preferred ring 4 compounds, wherein is Q-34.

87) A is A-1, L is L-2, and Q
Preferred Ring 4 compounds wherein is Q-35.

88) A is A-1, L is L-2, and Q
Preferred Ring 4 compounds, wherein is Q-36.

89) A is A-1, L is L-2, and Q
Preferred Ring 4 compounds, wherein is Q-37.

90) A is A-1, L is L-2, and Q
Preferred ring 4 compounds, wherein is Q-38.

9]) A is A-1, L is L-2, and Q
Preferred ring 4 compounds, wherein is Q-39.

92) A is A-1, L is L-2, and Q
Preferred Ring 4 compounds, wherein is Q-40.

93) A is A-1, L is L-2, and Q
Preferred ring 4 compounds, wherein is Q-41.

94) A is A-1, L is L-2, and Q
Preferred ring 4 compounds, wherein is Q-42.

95) A is A-1, L is L-2, and Q
Preferred Ring 4 compounds, wherein is Q-43.

96) A is A-1, L is L-2, and Q
Preferred Ring 4 compounds, wherein is Q-44.

97) A is A-1, L is L-2, and Q
Preferred Ring 4 compounds, wherein is Q-45.

98) A is A-1, L is L-2, and Q
is Q-46, compounds of preferred application 4.

9) A is A-1, L is L-2, and Q
is Q-47, compounds of preferred application 4.

100) Compounds of preferred application 4, where A is A-1, L is L-2, and Q is Q-48.

101) Compounds of preferred application 4, wherein A is A-1, L is L-3, and Q is Q-1.

102) Compounds of preferred application 4, where A is A-1, L is L-3, and Q is Q-2 103) A
is A-1, L is L-3, and Q-6;
-3, the compounds of preferred application 4.

104) fH compounds of preferred application 4, wherein A is A-], L is L-3, and Q is Q, -4.

]05) Compounds of preferred application 4, where A is A-1, L is L-3, and Q is Q-5.

106) Compounds of preferred application 4, wherein A is A-1, L is L-3, and Q is Q-6.

1Q7) Compounds of Preferred Application 4, wherein A is A-1, L is L-3, and Q is Q-7.

108) Compounds of preferred application 4, wherein A is A-1, L is L-3, and Q is Q-8.

109) Compounds of preferred application 4, wherein A is A-1, L is L-3, and Q is Q-9.

110) Compounds of preferred application 4, wherein A is A-1, L is L-3, and Q is Q-1o.

l1l) Compounds of preferred application 4, wherein A is A-1, L is L-3, and Q is Q-11.

112) Compounds of preferred application 4, wherein A is A-1, L is L-3, and Q is Q-12.

]13) Compounds of preferred application 4, where A is A-1, L is L-3, and Q is Q-13.

114) Compounds of preferred application 4, wherein A is A-1, L is L-3, and Q is Q-]4.

115) A is A, -1, L is L-3,
and compounds of preferred application 4, where Q is Q-15.

116:'l Compounds of preferred application 4, wherein A is A-1, L is L-3, and Q is Q-16.

117) Compounds of preferred application 4, wherein A is A-1, L is L-3, and Q is Q-17.

118) Compounds of preferred application 4, wherein A is A-1, L is L-3, and Q is Ω-18.

+19) Compounds of preferred application 4, where A is A-1, L is L-3, and Q is Q-19.

120) Compounds of preferred application 4, where A is A-1, L is L-3, and Q is Q, -20.

121) Compounds of preferred application 4, wherein A is A-1, L is L-3, and Q is Q-21.

122) Compounds of preferred application 4, which are A-6EA-1, L is L-3, and Q is Q-22.

121N A is A-], L is L-3, and Q, :6:Q, -23.

124) Compounds of preferred application 4, wherein A is A-1, L:L-3, and Q is Q-24.

125”l A is A-1, L is L-3,
and compounds of preferred application 4, where Q is Q-25.

126) Compounds of preferred application 4, wherein A is A-1, L is L-3, and Q is Q-26.

127) Compounds of preferred application 4, where A is A-1, L is L-3, and Q is Q-27.

128) Compounds of preferred application 4, wherein A is A71, L is L-3, and Q is Q-28.

129) Compounds of preferred application 4, where A is A-1, L is L-3, and Q is Q-29.

130) Compounds of preferred application 4, wherein -A is A-1, L is L-3, and Q is Q-30.

131) A is A-1 and H,, L is L-3,
and compounds of preferred application 4, where Q is Q-31.

132) Compounds of preferred application 4, where A is A-1, L is L-3, and Q is Q-32 133
) Compounds of preferred application 4, wherein A is A-1, L is T, -3, and Q is Q-33.

134) A is A-1 and IIXL is L-3,
And Q is Q-34, good application 4, f-hi-join, things.

135'l A is A-1, L is L-3,
and compounds of preferred application 4, where Q is Q-35.

1.36) Compounds of preferred application 4, where A is A-1, L is L-3, and Q is Q-36.

137) Compounds of preferred application 4, wherein A is A-1, L is L-3, and Q is Q-37.

138) Preferred Ring 4 compounds, wherein A is A-1, L is L-3, and Q is Q-38.

139) Preferred Ring 4 compounds, wherein A is A-1, L is L-3, and Q is Q-39.

140) Preferred Ring 4 compounds, wherein A is A-1, hXL is L-3, hl and Q is Q-40.

141) Preferred Ring 4 compounds, wherein A is A-1, L is L-3, and Q is Q-41.

1423 N is At-1 and It, I is L-3
Preferred ring 4 compounds, where Q is Q-42.

143) Preferred ring 4 compounds, wherein A is A-1, L is L-3 and 1 and Q is Q-43.

144) Preferred ring 4 compounds, wherein A is A-1, Lh; L-3, and Q is Q-44.

145) Preferred ring 4 compounds, wherein A is A-1, L is L-3, and Q is Q-45.

146) Preferred ring 4 compounds, wherein A is A-1, L is L-3, and Q is Q-46.

147) Preferred ring 4 compounds, wherein A is A-1, L is L-3, and Q is Q-47.

148) Preferred Ring 4 compounds, wherein A is A-1, L is L-3, and Q is Q-48.

149) Preferred ring 4 compounds, wherein A is A-1, L is L-4 and Q is Q-1.

150) Preferred ring 4 compounds, wherein A is A-1, L is L-4, and Q is Q-2.

151) Preferred ring 4 compounds, wherein A is A-1, hlL is L-4, hl and Q is Q, -3.

152) Preferred ring 4 compounds, wherein A is A-1, hXL is L-4, and Q is Ql-4.

153) Preferred ring 4 compounds, wherein A is AL-1, L is L-4, and Q is Q-5.

154) Preferred Ring 4 rH compounds, wherein A is A-1, L is L-4, and Q is Q-6.

155> A is A-1, L is L-4, dust,
and preferred ring 4 compounds, wherein Q is Q-7.

156) Preferred Ring 4 compounds wherein A is A-1, L is L-4 and Q is Q-8.

157) Preferred Ring 4 compounds, wherein A is A-1, L is L-4 and Q is Q-9.

158) Preferred Ring 4 compounds, wherein A is A-1, L is L-4, and Q is Q-10.

159) Preferred ring 4 compounds, wherein A is A-1, L is L-4, and Q is Q-11.

160) Preferred Ring 4 compounds, wherein A is A-1, L is L-4, and Q is Q-12.

161) Preferred Ring 4 compounds, wherein A is A-1, L is L-4, and Q is Q-13.

162) Preferred Ring 4 compounds, wherein A is A-1, L is L-4, and Q is Q-14.

163) Preferred Ring 4 compounds, wherein N is A-1, L is L-4, and Q is Q-15.

164) Preferred Ring 4 compounds, wherein A is A-1, L is L-4, and Q is Q-16.

165) Preferred Ring 4 compounds, wherein A is A-1, L is L-4, and Q is Q-17.

166) Preferred Ring 4 compounds, wherein A is A-1, L is L-4, and Q is Q-18.

167) Preferred Ring 4 compounds, wherein A is A-1, L is L-4, and Q is Q-19.

168) Preferred Ring 4 compounds, wherein A is A-1, L is L-4, and Q is Q-20.

169) Preferred Ring 4 compounds, wherein A is A-1, L is L-4, and Q is Q-21.

170) Preferred Ring 4 compounds, wherein A is A-1, L is L-4, and Q is Q-22.

171) Preferred Ring 4 compounds, wherein A is A-1, L is L-4, and Q is Q-23.

172) Preferred Ring 4 compounds, wherein A is A-1, L is L-4, and Q is Q-24.

173) Preferred ring 4 compounds, wherein A is human-1, L is L-4, and Q is Q-25.

174) Preferred Ring 4 compounds, wherein A is A-1, L is L-4, and Q is Q-26.

175) Compounds of preferred application 4, wherein A is A-1, L is L-4, and Q is Q-27.

176) Preferred Ring 4 compounds, wherein A is A-1, L is I, -4, and Q is Q-28.

177) Preferred Ring 4 compounds, wherein A is A-1, L is L-4, and Q is Q-29.

178) Preferred Ring 4 compounds, wherein A is A-1, L is L-4, and Q is Q-30.

179) Preferred ring 4 compounds, wherein A is A-1, L is L-4, and Q is Q-31.

180) There is A-1 Te, L is L-4”9+,
and preferred ring 4 compounds, wherein Q is Q-32.

181) Compounds of preferred application 4, wherein A is A-1, L is L-4, and Q is Q-33.

182) Preferred Ring 4 compounds, wherein Human is A-1, L is L-4, and Q is Q-34.

183) Preferred Ring 4 compounds, wherein A is A-1, L is L-4, and Q is Q-35.

184) Preferred Ring 4 compounds, wherein A is A-1, L is L-4, and Q is Q-36.

185) Preferred Ring 4 compounds, wherein A is A-1, L is L-4, and Q is Q-37.

186) Preferred Ring 4 compounds, wherein A is A-1, L is L-4, and Q is Q-38.

187) Preferred ring 4 compounds, wherein A is A-1, L is L-4, and Q is Q-39.

18s) Preferred Ring 4 compounds, wherein A is A-1, L is L-4 and Q is Q-40.

]-89) Preferred Ring 4 compounds, wherein A is A-1, L is L-4, and Q is Q-41.

190) Preferred Ring 4 compounds, wherein A is A-1, L is L-4, and Q is Q-42.

191) Preferred Ring 4 compounds, wherein A is A-1, L is L-4, and Q is Q-43.

192) A is A-1, L is I, -4,
and preferred ring 4 compounds, wherein Q is Q-44.

193) Preferred Ring 4 compounds, wherein A is A-1, L is L-4, and Q is Q-45.

194) A is A-1, L is I, -4,
and preferred ring 4 compounds, wherein Q is Q-46.

195) Preferred Ring 4 compounds, wherein A is A-1, L is L-4, and Q is Q-47.

196) Preferred Ring 4 compounds, wherein A is A-1, L is L-4, and Q is Q-48.

197,) A is A-1, L is L-5,
and preferred ring 4 compounds, wherein Q is Q-1.

198) Preferred ring 4 compounds, wherein A is A-1, L is L-5, and Q is Q-2.

1.99) Preferred ring 4 compounds, wherein A is A-1, L is L-5 and Q is Q-3.

200) Preferred Ring 4 compounds, wherein A is A-1, L is L-5, and Q is Q-4.

201) A is A-1, J='L-s,
and preferred ring 4 compounds, wherein Q is Q-5.

202) Preferred ring 4 compounds, wherein A is A-1, L is L-5 and Q is Q-6.

203) Preferred Ring 4 compounds wherein A is A-1, L is L-5 and Q is Q-7.

204) Preferred Ring 4 compounds, wherein A is A-1, L is L-5 and Q is Q-8.

205) Preferred Ring 4 compounds, wherein A is A-1, L is L-5, and Q is Q-9.

206) Preferred Ring 4 compounds, wherein A is A-1, L is L-5, and Q is Q-10.

207) Preferred Ring 4 compounds, wherein A is A-1, L is L-5, and Q is Q-11.

208) Preferred Ring 4 compounds, wherein A is A-1, L is L-5, and Q is Q-12.

209) Preferred Ring 4 compounds, wherein A is A-1, L is L-5, and Q is Q-13.

210) Preferred Ring 4 compounds, wherein A is A-1, L is L-5, and Q is Q-14.

211) Preferred Ring 4 compounds, wherein A is A-1, L is L-5, and Q is Q-15.

212) Preferred Ring 4 compounds, wherein A is A-1, L is L-5, and Q is Q-16.

213) Preferred Ring 4 compounds, wherein A is A-1, L is L-5, and Q is Q-17.

214) Preferred Ring 4 compounds, wherein A is A-1, L is L-5, and Q is Q-18.

215) Preferred Ring 4 compounds, wherein A is A-1, L is L-5, and Q is Q-19.

216) Preferred Ring 4 compounds, wherein A is A-1, L is L-5, and Q is Q-20.

217) Preferred ring 4 compounds, wherein A is A-1, L is L-5 and υ, and Q is Q-21.

218) Preferred Ring 4 compounds, wherein A is A-1, L is L-5, and Q is Q-22.

219) Preferred Ring 4 compounds, wherein A is A-1, L is L-5, and Q is Q-23.

220) Preferred ring 4 compounds, wherein A is A-1, L is L-5, and Q is Q-24.

221) Preferred Ring 4 compounds, wherein A is A-1, L is L-5, and Q is Q-29.

222) A is A-1, L is I, -5,
and preferred ring 4 compounds, wherein Q is Q-30.

223) Preferred Ring 4 compounds, wherein A is A-1, L is L-5, and Q is Q-31.

224) Preferred Ring 4 compounds, wherein A is A-1, L is L-5, and Q is Q-32.

225) Preferred Ring 4 compounds, wherein A is A-1, L is L-5, and Q is Q-33.

226) Preferred Ring 4 compounds, wherein A is A-1, L is L-5, and Q is Q-34.

227) Preferred Ring 4 compounds, wherein A is A-1, L is L-5, and Q is Q-35.

228) Preferred Ring 4 compounds, wherein A is A-1, L is L-5, and Q is Q-36.

229) A is A-1, L is I, -5,
and preferred ring 4 compounds, wherein Q is Q-37.

230) Preferred Ring 4 compounds, wherein A is A-1, L is L-5, and Q is Q-38.

231) Preferred Ring 4 compounds, wherein A is A-1, L is L-5, and Q is Q-39.

232) Preferred Ring 4 compounds, wherein A is A-1, L is L-5, and Q is Q-40.

233) Preferred ring 4 compounds, wherein A is A-1, L is L-6 and Q is Q-1.

234) Preferred ring 4 compounds, wherein A is A-1, L is L-6 and Q is Q-2.

235) Preferred Ring 4 compounds, wherein A is A-1, L is L-6 and Q is Q-3.

236) Preferred Ring 4 compounds, wherein A is A-1, L is L-6 and Q is Q-4.

237) Preferred Ring 4 compounds wherein A is A-1, L is L-6 and Q is Q-5.

238) Preferred Ring 4 compounds wherein A is A-1, L is L-6 and Q is Q-6.

239) Preferred Ring 4 compounds wherein A is A-1, L is L-6 and Q is Q-7.

240) Preferred Ring 4 compounds, wherein A is A-1, L is L-6 and Q is Q-8.

241) Preferred Ring 4 compounds, wherein A is A-1, L is L-6 and Q is Q-9.

242) Preferred Ring 4 compounds, wherein A is A-1, L is L-6 and Q is Q-10.

243) Preferred Ring 4 compounds, wherein A is A-1, L is L-6, and Q is Q-11.

244) Preferred Ring 4 compounds, wherein A is A-1, L is L-6 and Q is Q-12.

245) Preferred Ring 4 compounds, wherein A is A-1, L is L-6 and Q is Q-13.

246) Preferred Ring 4 compounds, wherein A is A-1, L is L-6 and Q is Q-14.

247) Preferred ring 4 compounds, wherein A is A-1, L is L-6, and Q is Q-15.

248) Preferred Ring 4 compounds wherein A is A-1, L is L-6 and Q is Q-16.

249) Preferred Ring 4 compounds, wherein A is A-1, L is L-6 and Q is Q-17.

250) Preferred Ring 4 compounds, wherein A is A-1, L is L-6, and Q is Q-18.

251) Preferred Ring 4 compounds, wherein A is A-1, L is L-6 and Q is Q-19.

252) Preferred Ring 4 compounds wherein A is A-1, L is L-6 and Q is Q-20.

253) Preferred Ring 4 compounds, wherein A is A-1, L is L-6, and Q is Q-21.

254) Preferred Ring 4 compounds, wherein A is A-1, L is L-6 and Q is Q-22.

255) Preferred Ring 4 compounds, wherein A is A-1, L is L-6, and Q is Q-23.

256) Preferred Ring 4 compounds, wherein A is A-1, L is L-6 and Q is Q-24.

257) Preferred Ring 4 compounds wherein A is A-1, L is L-6 and Q is Q-29.

258) Preferred Ring 4 compounds wherein A is A-1, L is L-6 and Q is Q-30.

259) Preferred Ring 4 compounds, wherein A is A-1, L is L-6 and Q is Q-31.

260) Preferred Ring 4 compounds, wherein A is A-1, L is L-6, and Q is Q-32.

261) Preferred Ring 4 compounds, wherein A is A-1, L is L-5, and Q is Q-33.

262) Preferred Ring 4 compounds, wherein A is A-1, L is L-5, and Q is Q-34.

263) Preferred Ring 4 compounds, wherein A is A-1, L is L-5, and Q is Q-35.

264) Preferred Ring 4 compounds, wherein A is A-1, L is L-6, and Q is Q-36.

265) Preferred Ring 4 compounds, wherein A is A-1, L is L-5, and Q is Q-37.

266) Preferred Ring 4 compounds, wherein A is A-1, L is L-6, and Q is Q-38.

267)' Preferred ring 4 compounds, wherein A is A-1, L is L-6, and Q is Q-39.

268) Preferred Ring 4 compounds, wherein A is A-1, L is L-6, and Q is Q-40.

269) Preferred Ring 4 compounds, wherein A is A-1, L is L-7, and Q is Q-1.

270) Preferred ring 4 compounds, wherein A is A-1, L is L-7 and Q is Q-2.

271) Preferred Ring 4 compounds, wherein A is A-1, L is L-7 and Q is Q-3.

272) Preferred Ring 4 compounds, wherein A is A-1, L is L-7, and Q is Q-4.

273) Preferred Ring 4 compounds, wherein A is A-1, L is L-7, and Q is Q-=s.

274) Preferred Ring 4 compounds, wherein A is A-1, L is L-7 and Q is Q-6.

275:') Preferred Ring 4 compounds, wherein A is A-1, L is L-7, and Q is Q-7.

276) Preferred Ring 4 compounds, wherein A is A-1, L is L-7, and Q is Q-8.

277) Preferred Ring 4 compounds, wherein A is A-1, L is L-7, and Q is Q-9.

278) Preferred Ring 4 compounds, wherein A is A-1, L is I, -7, and Q is Q-10.

279) Preferred Ring 4 compounds, wherein A is A-1, L is L-7, and Q is Q-11.

280) Preferred Ring 4 compounds, wherein A is A-1, L is L-7, and Q is Q-12.

281) Preferred Ring 4 compounds wherein A is A-1, L is L-7 and Q is Q-13.

282) Preferred Ring 4 compounds, wherein A is A-1, L is L-7, and Q is Q-14.

283) Preferred Ring 4 compounds wherein A is A-1, L is L-7 and Q is Q-15.

284) Preferred Ring 4 compounds wherein A is A-1, L is L-7 and Q is Q-16.

285) Preferred Ring 4 compounds, wherein A is A-1, L is L-7, and Q is Q-17.

286) Preferred Ring 4 compounds, wherein A is A-1, L is L-7 and Q is Q-18.

287)' Preferred Ring 4 compounds, wherein A is A-1, L is -7, and Q is Q-19.

288) Preferred Ring 4 compounds, wherein A is A-1, L is L-7, and Q is Q-20.

289) Preferred Ring 4 compounds, wherein A is A-1, L is L-7, and Q is Q-21.

290) Preferred Ring 4 compounds wherein A is A-1, L is L-7 and Q is Q-22.

291) Preferred Ring 4 compounds, wherein A is A-1, L is L-7, and Q is Q-23.

292) Preferred Ring 4 compounds, wherein A is A-1, L is L-7, and Q is Q-24.

293) Preferred Ring 4 compounds, wherein A is A-1, L is L-7, and Q is Q-29.

294)' Preferred Ring 4 compounds, wherein A is A-1, L is L-7 and Q is Q-30.

295) Preferred Ring 4 compounds, wherein A is A-1, L is L-7, and Q is Q-31.

296) Preferred Ring 4 compounds, wherein A is A-1, L is L-7, and Q is Q-32.

297) Preferred Ring 4 compounds wherein A is A-1, L is L-7 and Q is Q-33.

298”l A is A-1, L is L-7,
and compounds according to preferred item 4, wherein Q is Q-34.

299) Compounds of preferred item 4, wherein A is A-1, L is L-7, and Q is Q-35.

300) Compounds of preferred item 4, wherein A is A-1, L is L-7, and Q is Q-36.

301) Compounds of preferred item 4, wherein A is A-1, L is L-7, and Q is Q-37.

3o2) Compounds of preferred item 4, wherein A is A-1''i?, L is L-7, and Q is Q-38.

303) Compounds of preferred item 4, wherein A is A-1, L is L-7, and Q is Q-39.

304) Compounds of preferred item 4, wherein A is A-1, L is L-7, and Q is Q-40.

Particularly preferred compounds of the invention because they are the easiest to synthesize and/or have the greatest herbicidal activity are N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl). -1,5-dimethyl-3-[5-
(Methylthio)-1,3゜4-oxadiazole-2-
yl]-xH-pyrazole-4-sulfonamide, melting point 201-203.5°C;
triazin-2-yl)-aminocarbonyl, :l-1
,5-dimethyl-3-[:5-(methylthio)-1,3
,4-oxadiazol-2-yl]-1H, pyrazole-4-sulfonamide, melting point 205-206.5°C;
・N-[(4-chloro-6-medquinpyrimidine-2
-yl)aminocarbonyl:]-]1,3-dimethyl-5-C5-2-propenylthio)-1,3,4-oxadiazol-2-yl)-18-pyrazole-4-sulfonamide, melting point 183 -185°C; ・N-[4,6-dimethoxypyrimidin-2-yl)
Aminocarbonyl': l-4-(5-mercapto-1,
3,4-oxadiazol-2-yl)-1,5-dimethyl-1H-pyrazole-3-sulfonamide, melting point 2
02-204°C; and 3-1: [(4,6-dimethoxypyrimidine-2-
yl)aminocarbonylcoaminosulfonyl:]-1-
(2-pyridinyl)-1H-pyrazole-4-carboxylic acid methylesterenope has a melting point of 183-188°C.

The compounds of Synthesis 2.2 can be produced by one or more of the methods described in Reaction Schemes 1, 2.3 and 4 below.

Formula I, where W is O, as shown in Reaction Scheme 1 below:
Compounds of formula 2 can be prepared by treating sulfonamides of formula 2 with pyrimidine or triazinecarbamic acid methyl esters of formula 3 in the presence of equimolar amounts of trimethylaluminum.

[where AXRl, Q and R2 are as defined above and R is H].

The reaction of Scheme 1 is best carried out under an inert atmosphere at temperatures between 23 DEG and 83 DEG C. in an inert solvent such as methylene chloride or 1,2-dichloroethane for 12 to 96 hours. The product can be isolated by addition of aqueous acetic acid and subsequent extraction of the product in methylene chloride or direct filtration for products of low solubility. The product is generally n-butychloride! It can be purified by feeding with solvents such as ethyl acetate or diethyl ether or by chromatographic steps.

Methyl carbamates 3 can be conveniently prepared by treating the corresponding heterocyclic amines 2-6 with dimethyl carbonate or methyl chloroformate in the presence of a base such as sodium hydride or pyridine.

Details regarding this reaction and the preparation of carbamates of formula 3 are described in European Patent Application No. 83.975 (published July 20, 1983).

On the other hand, compounds of formula (1) in which W is O are prepared by adding an equimolar amount of the second sulfonamide, for example, 1,8-diaza-biaclo[5,4,O]-undec-7-ene (DBU). It can be prepared by reacting with a suitable phenyl ester of carbamic acid 4 in the presence of a tertiary amine base such as tertiary amine base.

Scheme 2: where R2, AXR, and Q are as defined above, and R is H. Best performed in active solvents. European Patent Application No. 70,804 (1
Treatment with an aqueous acid solution to give the desired product according to the teachings of South African Patent Applications 825,042 and 830°441. Phenyl carbamates 4 can be prepared by treating the corresponding heterocyclic amines of 26 with diphenyl carbonate or phenyl chloroformate in the presence of a base such as sodium hydride or pyridine.

A number of compounds of 2I can also be obtained by reacting a suitable sulfonyl isocyanate or sulfonyl inthiocyanate 5 with a suitably redeemed aminoheterocycle 6 as shown in the following reaction scheme 3. Can be manufactured.

Reaction formula 3 % formula % [In the formula, except that R1 is other than H, R2, kXRXR,
and W are as defined above] This reaction can be carried out, for example, by methylene chloride, tetrahydrofuran,
2 in acetonitrile or toluene-like active solvents.
Best performed at 3° to 100°C for 1 to 24 hours. If the products are insoluble in the reaction solvent, they can be isolated by simple filtration. When the products are soluble, they can be removed by evaporation of the solvent and e.g.
- Can be isolated by feeding and filtration of the residue using a suitable solvent such as chlorobutane, diethyl ether, methanol or ethyl acetate. The product can be further purified by a column chromatography step.

The sulfonyl isocyanates of formula 5 above, where W=0, are disclosed in US Pat.
can be prepared from the corresponding sulfonamides of formula 2 in a manner similar to that described therein, although often in low yields. In a preferred method, sulfonamides are reacted with phosgene in the presence of n-butyl isocyanate and a tertiary amine catalyst under reflux in an inert solvent such as xylene. A preferred catalyst is 1,4-diazapinechloro (
ZZ2) Octane (DABCO). On the other hand, incyanate 5 is prepared by (1) sulfonamide 2 in an inert solvent such as 2-butanone under reflux.
- reacting with butyl and a base such as potassium carbonate to produce n-butylsulfonylurea, and (2)
This compound can be prepared by reacting with phosgene and a DABCO catalyst in a xylene solvent under reflux.

Sulfonyl isothiocyanates are K, Hartke ()r
Arch.

Pharm, ') 299.174 (1966), sulfonamides can be prepared from K by treating the sulfonamides with carbon disulfide and potassium hydroxide and then reacting the dipotassium salt with phosgene.

Some of the compounds of Formula I can also be prepared as shown in Scheme 4.

Reaction formula 4 [In the formula, Y' is CH3, C2H,, CH2C) T2F, CH2
CHF2 or CH2CF, and J, R2 and Q are as defined above, except that R1 is other than H.] This reaction sequence is described in European Patent Publication No. 30,140.
and the necessary heterocyclic incyanates of formula 7 are prepared according to the process disclosed in Swiss Patent No. 579,0.
62, U.S. Patent 3,919,228, U.S. Patent 3,73
2,223 and U, 7 on Gitsuikki (C)izy
cki)'s Angewante Hemii International Edeinyong Ying In 1976.10, 40
It can be produced according to the method described on pages 2 and 403.

A number of sulfonamides of Formula 2a, where Q is Q-1 to Q-24 or Q-29 to Q-40, can be prepared by the reaction sequence shown in Scheme 5 below.

Reaction formula 5% formula% [wherein, except that R1 is other than H, R1 and R2 are as defined above, and Q is Q, -1 to Q-2
4 or Q-29 to Q-40, and L is L1 to L4] The reaction of reaction scheme 5(a, b) is described in European Patent Application 83.
975 and 85.476 (July 2, 1983 respectively)
It can be carried out by a method similar to that described in the following publication (published on August 10, 1983). The reaction of Scheme 5a is carried out by treating a solution of amine 9 in a mixture of concentrated hydrochloric acid and glacial acetic acid with an aqueous solution of sodium nitrite at 5°C to 5°C. After stirring for 10-30 minutes at about 0° C. to ensure complete diazotization, the solution is dissolved in excess sulfur dioxide and a catalytic amount of copper chloride (1) in glacial acetic acid.
or to a mixture of M(It) chloride at about 10°C. Keep the temperature at about 10°C for ~1 hour, then 20°C ~ 30°C.
℃ and hold at this temperature for 2 to about 24 hours. This solution is then poured into a large excess of ice water. Sulfonyl chloride 1
0 can be isolated by filtration or by extraction in a solvent such as ethyl ether, methylene chloride or preferably 1-chlorobutane and subsequent evaporation of the solvent.

The amination described in Scheme 5b is conveniently carried out by treating a solution of sulfonyl chloride 10 with at least 2 molar equivalents of anhydrous ammonia or aqueous ammonium hydroxide in an inert solvent such as tetrahydrofuran. Sulfonamides 2a are isolated by filtration, washing with water to remove by-product ammonium chloride, and concentrating the organic liquid. Sulfonamides can be further purified by crystallization or chromatography steps.

Certain sulfonamides of formula 2b, where Q is Q-7 to Q-13, as shown in Scheme 6, European Patent Application No. 83,975 and references cited therein. It can be manufactured in the same manner as described in . By carrying out the appropriate reactions taught in European Patent Source 83,975, or simple variations thereof, one skilled in the art can obtain formula 1 where Q is from Q-7 to Q-13.
N-t-butyl protected pyrazole sulfonamides of No. 2 can be prepared.

Reaction Scheme 6 (6a) [wherein L is L-1-L-4, R1 is other than H, RI and R2 are as defined above, and Q is Q -7~Q-13
and J is a suitable functional group as taught in the European patent volume @ 83,975 and this cited document for preparing Q groups Q-7 to Q-13] In some cases t- Removal of the butyl protecting group can be carried out simultaneously with the heterocycle addition step, but most often requires treatment with trifluoroacetic acid or an acidic catalyst in an alcoholic solvent. Sulfonamides of formula 11 are found in European Patent Source 95,925 and European Patent Volume, @ 87
．． ．． 780 or a simple modification thereof,
Those methods should be obvious to those skilled in the art.

Sulfonamides of formula 2C containing pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl or triazinyl groups, where Q is Q-31-Q-40, can be prepared by the reaction sequence outlined in Scheme 7.

Reaction formula 7 [In the formula, L is L-1, L-2 and T, -4, and X/ is 4-
Br in position and H in the 5-position, QfdQ-31 to Q-4o, R4 is as defined above except that R8 does not represent H, and R21-1: As defined above] Formula 2C
The compounds of European Patent Application No. 85,476 (198
Manufactured in the same manner as the teachings of the publication published on August 10, 2013).

Scheme 7(a,b) The N t-butylsulfonamide of formula 14 is dissolved in an ethereal solvent such as tetrahydrofuran, and 2 equivalents of n-butyllithium in hexane is dissolved at about -70
Add at °C. After 1-5 hours at about -70°C, a compound of formula 15 is formed. This is isolated but 1 equivalent of copper iodide ([1] is added at about -70°C followed by 1 to 1.5 equivalents of the appropriately substituted heteroaromatic iodide of formula 16. The reaction mixture 1 to 06 to 70℃
Heat for 3 days, concentrate and pour onto aqueous ammonia.

Compounds of formula 12a are isolated by filtration if clear or by extraction and concentration with methylene chloride if oil. Compounds 12a can be further purified by recrystallization or chromatography steps.

The compounds of formula 16 above are Interscience e
They can be prepared according to methods known in the art, such as those described in the series "Chemistry of Heterocyclic Compounds" published by Publications, New York, London, the teachings of which are incorporated herein by reference. Iodopyridines are described in volume 14 of the above series, pages 407-488. Iodopyrimidines, J. Brown and S. F. Mason.
It is written in the 16th volume of the above series by N. Iodopyrazines are manufactured by A, Hill/Huberg (H
+rshb6rg) and P, E, Spoe
i) The Journal of the Organic, Chemist'J I (J, Org, Chem,), 26.19
07 (1981) and iodopyridazines, L. Aldons.
) and R., N. Castle, Volume 28 of the Interscience Series, 240
- It is written on page 241. Iode-1,3゜5-
Triazines include E, M, Smolin, and Raboport.
Rykowsky (Rykowsky) and ``Process for the preparation of iodo-1,2,4-1-IJ azines'' are described in volume 13 of the above series by Rykowsky.
Sat C, van der Jlz-plus (van der P
I6s ``IK yo υ The Journal of Organic Chemistry (J.

taught.

Scheme 7(C) This reaction combines the compound of formula 12a with 2-10 trifluoroacetic acid with or without an inert solvent.
It is carried out by heating at 0-70°C for 1-3 days. Product 2C can be isolated as the trifluoroacetate salt by evaporation of the solvent and excess acid and feeding with ether.

The free base is obtained by neutralizing the salt with aqueous base, extracting in an organic solvent, and concentrating the organic extract. Product 2C can be further purified by recrystallization or chromatography steps. Sulfonamides of formula 14 are described in European Patent Application 95,925 and European Patent Application 8.
7.780 or simple variations thereof.

Certain sulfonamides containing tetrahydrofuranyl, tetrahydropyranyl, dihydrofuranyl or dihydropyranyl groups are similar to the teachings of European Patent Application 84.476 as shown in Schemes 8 and 9. It can be manufactured by

Reaction Scheme 8 (8a) [wherein A is as defined above except that R1 does not represent H, X" is Br or CI, and L is L-1, L-2 or L-4] Reaction formula 3 ('
aXb) Reaction of dirithiosulfonamides 15 with haloaldehydes of formula 17 in an inert solvent such as THF at temperatures between -78°C and 25°C to give virazole alkoxides, which are then subjected to intramolecular cyclization. Cyclic ethers 18
shall be. These are then deprotected to provide the corresponding sulfonamides by the step of Scheme 7c.

Dihydrofuran or dihydropyran group (Q-41,4
Sulfonamides of formula 22 containing 2) can be produced by the method shown in reaction scheme 9.

Scheme 9 %Formula % L is L-1 to 'L-4, and R1 and R2 are as defined above] In this reaction, a sulfonamide of formula 20 is reacted with e.g. carbon tetrachloride or chloroform. The mixture is treated with 1 equivalent of N-chlorosuccinimide at O'-60 DEG C. for 2-24 hours in a similar solvent. The by-product succinimide is removed by filtration and the solution is sent directly to the next step.

Reaction Scheme (9b) Sulfonamides of formula 21 are treated in carbon tetrachloride or chloroform solution at 0-60°C for 1-6 hours with at least 1 equivalent of triethylamine, DABCO.
, pyridine, nitrile methoxide or anhydrous potassium carbonate. The product is isolated by washing the organic solution with water, drying and slopping the solvent off. Sulfonamides of formula 22 are obtained in pure form by recrystallization or column chromatography.

Certain sulfonamides of Formula 2 are preferably prepared from appropriately substituted benzylthiosulfonamides of Formula 23 as shown in Scheme 10.

Formula 10% Formula % [where J is a suitable functional group as taught in European Patent Application 83,975 for preparing Q groups Q-1 to Q-20 and the references cited therein. Q is Q-1-Q-20, R71 and R2 are as defined above,
and R8 is H or alkyl] In this reaction process, a suitably functionalized thiopyrazole of formula 23 is prepared by formula 24 (Q-1 to Q -20) and the corresponding heteroaromatically substituted thiopyracites of Q-43. Mild oxidative chlorination of 24 gives the intermediate sulfonyl chloride, which is converted to the sulfonamide of formula 25 by treatment with ammonia in THF solution at temperatures between -35°C and 25°C.

The thiopyrazoles of formula 23 are T, leyforus (Li
Ijefors) and J. Sandström (Sa.
ndstrom) Acta Hemi Power Scandinavica A
cta Ch6mica 5candinavica)
, 1970.24.3109 or simple modifications thereof.

Other sulfonamides of Formula 29 can be easily prepared by the metallization step abbreviated in Reaction Scheme 11. 2H, W for a general description of metallization reactions.

Gschwend (Gs chw6nd) and iH,R
, Rodriquez's Organic Reactions (Org, React 1ons),
See 197'9.26.1.

Reaction Scheme 11 [wherein R1 is as defined above except that R1 is other than H, R2 is as defined above,
and Q is O-1 to Q-4, Q-14 to Q-20, and Q-
43] In this reaction process, a heteroaromatically substituted pyrazole of formula 26 is treated with one equivalent of n-butyllithium at -70 DEG to 25 DEG C. in an ethereal solvent such as tetrahydrofuran. - After 1-5 hours, a compound of formula 27 is formed. The lithium salt is then immediately treated with at least one dose of sulfur dioxide at a temperature between a<0>C and -50<0>C. After warming to 25° C., the lithium sulfinate of formula 28 is completely filtered off and sent directly to the next reaction.

Reaction Scheme (Ijc) Lithium sulfinates of formula 28 are converted to sulfonamides 29 by treatment with chloramine in ether at 0°C, then warming to 55°C and stirring for 2-24 hours. can be done. The product sulfonamides are isolated by extraction in a solvent such as ethyl acetate and subsequent evaporation of the solvent. Sulfo/amides are purified by recrystallization or column chromatography. For details of this process, please refer to G, H
, Coleman and C0R, Hauser's Journal * Op the American Chemical Society (Am, Chem,
Soc, ), 192 B, 50.1195 See all 1 Sulfinates of formula 28 were also prepared in a two-step process, namely by J. F. Scullley and E. V. Brown.・Glossy Op Organic Chemistry (J, Org, Che
m,), 1954.19.894, W, E, Trull (
Trull) and E.

Wellisch's The Journal of the American Chemical Industry (
J, Am, Chem, Soc, ), 1952.7
4.5177 rows (Y, K, Yurie
v) and N, Sadavaya's Journal of General Chemistry Op.
Ninisnisar (J-Gen, Chem.

USSR), 19b 4.54.1814 to give the intermediate sulfonyl chloride 2, and the sulfonyl chloride in an ethereal solvent such as THF. The pyrazoles of formula 26 can be converted to the sulbonamides 29 by treatment with ammonia at 20% by weight, and the pyrazoles of formula 26 can be converted to sulfonamides 29 from suitably functionalized pyrazoles.Patent Application No. 83.97
5 or simple variations thereof.

Anion 27 is generated as described for reaction 11a. Cool the entire tetrahydrofuran solution to -78°C and immediately treat with at least 1 equivalent of sulfuryl chloride at -78°C.

The entire reaction is warmed to 0°C and treated with a saturated solution of ammonium chloride. The organic solution is separated and aminated as described in reaction 11c. Alternatively, it is also possible to treat the crude sulfonyl chloride solution with ammonium carbonate and isolate the crude sulfonamide 29 directly.

Thiopyrazoles containing pyrazole, furan, thiophene or pyrrole substituents can be prepared by the reaction shown in Scheme 12.

Reaction formula 12 [In the formula, L=L-2, L-5 or L-4, Q''5.6.
21-24.29,! +O, R1 is as defined above except that R1 is other than H, and R2 is as defined above] Lithio compounds of formula 51 are bromo compounds of formula 30. by treatment with 1 equivalent of n-butyllithium at 170 DEG C. to 25 DEG C. in ether or tetrahydrofuran.

Details of this type of lithiation can be found in R.
tel) and M, E, Sehoen.
) of Justus Ltebigs Ann
Lithio compounds of formula 51, as described by , Chemie) 1, 959.625.55, can be converted to the corresponding sulfonamides by the same sequence of reactions outlined in Scheme 11(b and C).

Bromo compounds of formula 60 can be prepared by methods known in the art, some of which relate to furans>,)A,
P. Dunlop and F.

"Flans" by N. Peters,
Reinhold, New York, 1956, P. Bosshard and C. H. Oig,
x, Eugster Atopanthes in Heterocyclic O Chemistry (Adv, He t
ero-cyclic Chem, ) 1966.7
, 577: A. R. Jones on pyrroles (
Jones) and G. P. Bear, Chemistry of Viroles, Academic Press, New York, 1977;
; in Schof'ield) M
, R. Grimmett and B.R.

T. Keene, “Azoles”, Cambridge University Press, Kempritzme, 1976; and R. Fusco, “Chemistry of Heterocyclic Compounds” on pyrazoles, Interscience No. 7'
+7 Tsushyas, New E-li, 1967. Part 1: Pyrazoles.

Pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl group (Q-51 to Q-40), thiazoyl group (Q-17 to q-19), or chenyl group (Q'
-'25 and Q-24)e-containing sulfonamides of Formula 2 can be prepared as outlined in Scheme 16.

Reaction formula 15 %formula%) Saturday and Sunday (13c) R1R.

57 5B [wherein R and R2 are as defined above, Z+z'Z-2 and z3 are independently CH or N, 1, and QFiQ-[1 to Q-40] ] The reaction of reaction formula 15a is 1 to 2 at 50°C to 140°C.
The reaction is carried out for 4 hours in a solvent such as ethanol, toluene, dimethylformamide or an excess of methylalkanamide and methylacetal. The product can be isolated by evaporation of the solvent. For further information, see Technical Information Bulletin, "DMF Acetals", Aldrich Chemical, December 1973,
and Y, Lin and S, A, Lang.
ang) The Journal of Organic Chemistry (J, Org, Chem,), 1980.45
．． See the similar process described in No. 4837.

The reaction of Scheme 15b is carried out in an inert solvent such as ethanol at 25-100°C for 1-48 hours. Isomeric products are isolated by addition of water and extraction with ethyl acetate or methylene chloride.

The pyrazoles 35 and 56 can be separated by high pressure liquid chromatography by a person skilled in the art or sent in a mixture to the next reaction. For details on this reaction,
Y. Lin and S. A. Lang's Journal of Heterocyclic Chemistry (J.

Heterocyclic Chem, ), 1977
．． See 14°545.

The reaction of Scheme 15c is carried out in chloroform with excess bromine under reflux for 2 to 8 hours. The product is isolated by neutralization, extraction in a solvent such as methylene chloride, and removal of the solvent by evaporation. The pyrazoles 57 and 68 can be separated by chromatography at this stage or sent to the next reaction. Details of this process can be found in Lehütter 2H, Wagner (W
Just
us Liebigs Ann, Chemie))
1953.593.15.

The bromopyrazoles of formulas 57 and 58 are combined with reaction formula '12
and converted to their corresponding sulfonamides by step 11(bX c).

Aminopyrazoles of Formula 9 can be prepared by reduction of the corresponding nitropyrazole of Formula 39 as shown in Scheme 14.

Reaction formula 14 [wherein Q is Q-f to Q-24 and Q-43, R2 is as defined, and R1 is No on the phenyl ring, as defined except for 'i and LldL-1 to L-4] The reduction reaction of Scheme 14 can be carried out by methods known in the literature by those skilled in the art. For more information, please see European Patent Application No. 83.975 and 84.476'ik.
For further description of the method, see R.
Schofeld, M. R.
Grimmett and B, R.

See T. Keene, 17 Soles, Cambridge University Press, Cambridge, 1976, p. 233.

Nitropyrazoles of formula 59 are important intermediates for the preparation of many compounds of the present invention.

They can be produced by a person skilled in the art by applying suitable methods selected from various known literature methods.

For example, the nitropyrazoles of 259a can be prepared from suitably functionalized nitropyrazoles of formula 40 as shown in Scheme 15 by those skilled in the art using the teachings of European Patent Application No. 83,975 and cited therein. It can be manufactured in the same manner as in the reference cited in the paper.

Reaction Scheme 15 [wherein Q is Q-1 to Q-20 and Q-45, R1 and R2 are as defined, and J is the Q group Q-1 to Q-20 and Q- Nitropyrazoles of formula 40 have been described in various ways by those skilled in the art. It can be manufactured using all literature methods. Regarding the main literature, see R. Fusc6, ``Pyrazoles, Pyrazolines, Virazolisones, Indazoles, and Fused Rings'', Chemistry Series on Heterocyclic Compounds, Interscience Pritzschers, New York, NY1.
967, pp. 1-137; Shawfield, M.R.
.

Grimmett and B, R, F, Keene's Azoles', University of Cambridge, S, Balian
), K.C. VanErk's Tetra-hadron Le
tt.), 1970.479 and references cited therein.

Additionally, a furanthiophene or virol group (where Q is Q-
21 to Q-24, Q-29)
The nitropyrazoles of 9b can be prepared analogously to the teachings in European Patent Application No. 85,476 and the references cited therein as shown in Scheme 16a.

R,R.

[wherein R1 is as defined except for H, R2 is as defined, Q is Q-21 to Q-24 and Q-29, and L is L-1 ~L-4] That is, a furyl-, chenyl, or pyrrole copper compound of formula 42 is reacted with a promoter or iodonitropyrazole of formula 41 in a solvent such as pyridino or quinoline at 0°C to 60°C for 1 to 3 days. react with. The product 59b can be obtained by addition of an acid such as acetic acid and water, extraction with all over methylene chloride and removal of the solvent by evaporation, and the isolated compounds can be purified by chromatography. They are prepared by reacting the corresponding lithium reagent with cuprous iodide or cuprous bromide in an inert solvent such as ethyl ether. Detailed steps for similar types of reactions are given by M. Nilsson and C. Ullenius.
1entus) Acta Hemi'car scansonavi force (Acta, Chem.

5cand, ), 1970.24.2579, (:.

Acta, Chem, Scandinavica of Ullenius (Acta, Chem, 5cand,);
.

1972.26.5583.

R1DMF’　　　　R.

L Town [wherein R1 and R2 are as defined above, and Q is Q"45, Q-46, Q-47"! or Q-48, and L is L-1 to L-4.] Reaction 16b is carried out essentially as Reaction 16m, except that the solvent is N,N-trimethyl-formamide. Ru. Intermediate product 41b is obtained by removing the solvent in vacuo,
The compounds can be isolated by treatment of the residue with an acid such as acetic acid and water, extraction with ethyl acetate, and removal of the solvent by evaporation.The compounds can be purified by chromatography.

Potassium compounds of formula 42a are prepared by reacting the heterocycle Q with potassium hydride in N,N-trimethylformamide. Product 41e is intermediate product 4l
b'i obtained by stirring in trifluoroacetic acid for one day or more.

41a/ [wherein R is CH,,C2H, R1, Rlg and R□ are as defined above and LFi, L-1 to L-4] of formula 41c' The compounds are Y, Karasawa
wa), K, Suzuki, S.

Nakamura, K., Mo.
riyama) and A, Takeda.
Heterocycles, Embryo, 695 (1984).

(as shown in Reaction Scheme 17 below) tetrahydrofuran or tetrahydrothiophene group (Q is Q-25~
Sulfonamides of formula 2e containing sulfonamides of formula 2d (Q-28) are prepared by catalytic reduction of the corresponding furan or thiophene group (Q' is Q-21 to Q-24) of sulfonamides of formula 2d. can.

Reaction formula 17% Formula% [In the formula, Q' is Q-21 to Q-24, Q is Q-25 to Q-28, and R1 and R2
is as defined above] Selective reductions of the type shown in Scheme 17 are well known in the literature. The selection of catalysts, solvents, pressures and temperatures for the reduction of furans is very important! -(Sevan
desh) 1 furans, A, P.

Dunlop and 0: V, N. Beters, Reinhold Publishing Corporation, New York, NY 1955. pp. 674-715 and P. N., Ryl and r. 1 Catalytic Hydrogenation in Organic Synthesis, Academic Press. , 1'979
．． It is described on pages 227-234. Reduction of thiophenes by H, D, Hartough, 1 Thiophene and its Derivatives”, Chemistry of Heterocyclic Compounds Series, Interscience Publishers, Inc., New York, NY 1952.1
It is described on pages 67-169.

Reaction formula 7.8.11.12.16a116b and 16
In step c, the substituent for R1 needs to be compatible with the reaction conditions. Suitable protecting groups can be used if necessary. those tetrahydropyranyl of pyrazole nitrogen,
Protection as methoxyethoxymethyl or t-butyl ethers and subsequent protection group removal and nitrogen functionalization is taught in European Patent Application 95,925.

A process similar to that abbreviated in Reaction Scheme 18 is carried out in Formula 2.
This is another process for producing pyrazole sulfonamides of f.

Reaction formula 18% Formula% (18b) ■ g [wherein P is a protecting group as above, Q and R2 are as defined above, and ゛ L is L-1 to L-4 Sulfonamides of formula L-5 (compound 47) in which QXR2, Ra-R83 and R14 are as defined above are shown in Scheme 19.19a below.

19b and 20.

On the other hand, compounds of formula 47 can be prepared from amine 45 through the process abbreviated in reaction formula t9a below.

Decarbo R2H The reactions described in Equations 19 and 19a are well known from the literature and for major references see R. Fusco's 1-pyrazoles, pyrazolines, pyrazolidines, indazoles and fused rings. , Heterocyclic Compounds Chemistry Series, Interscience, 6 Princes, New York, NY 1967. See all pages 1-157.

The sulfonamide of structural formula 47 has the reaction formula 19b (RzΦ
C1) from dithioketene acetals such as 45c.

5c 5a Hydrazine 447 can be reacted with intermediates 45c, the latter being known from the literature and can be prepared by a person skilled in the art. Regarding the main references, see Sandström and Wennerbeck's Aknigonno# -
(Gompper) and Toepfl's Chem.

Ber, ), 95.2861 (1962) and the references cited therein, Intermediates 4
5a and 451) can be processed using the steps described in Schemes 19 and 19a to provide a number of other synthetic pyrazoles 47.

Reaction Scheme 20 Meanwhile, 50 is N-protected, protected 51'(i1'' is synthesized, and then 2 protecting groups are removed to give 52. In this step, both isomers 47 and 52 (L-7) are synthesized. Give 2.

Sulfonamides of formula L-6 (compounds 55 and 59), where QsR1-R13, R15 and RI6 are as defined above, are represented by Reaction Schemes 21.22a, 22
b, 25a and 23b.

Reaction Formula 21 % Formula % The process of Reaction Formula 21 requires that the substituents have affinity with the reaction conditions. Therefore, R1, is initially Br)CO2
R17t or a halogenated side chain and P is an acid-sensitive protecting group such as, for example, CH(OR)2. Schemes 11a-11d describe the metallization of pyrazoles and their subsequent reaction with electrophiles. Chlorosulfonation and N-alkylation reactions are well known in the literature.

Examples of these reactions include -R, Cremlin (Cre
mlyn), F, Swinbourne
) and M. Yung's glossary op heterocyclic chemistry (J.

Het, Chem, ), 1B, 997 (1981) and ■, Final and G, Lord (
The Journal of the Chemical Society (J, Chem, Soc, )) ss14 (1
See q57).

Reaction formula 22 [In the formula, R2 and R16 are alkyl, and alkoxy group is alkoxyalkyl] (22b) Q Q57a
iL where R1ff is alkyl, alkoxycarbonyl or alkoxyalkyl Compounds such as 56 and 56a in Schemes 22a and 22b can be prepared by those skilled in the art.

Reaction formula 23% formula%) [In the formula, R□ is C1, Br or SH] 60 and 60
Compounds such as a are known in the art and include 1. and can be manufactured by experts in the art. Compounds 55 and 59
Further process R1! It should be obvious to those skilled in the art that other derivatives of RI6 and RI6 can be provided. Information regarding the thiolation of 60 and 60a to thiols is available from GiorL.
) Other Il Ken Farmaco (11 Farmaco), Ed
.

Sc, 58.274 (1983), R. Olsen (O
The Journal of Organic Chemistry (J. Isen) and H. Snyder (J.
, Org, Chem, ), 50.184 (1965).

Q% Sulfonamides of formula L-7 (compound 52), where R2, Re-RI3 and R14 are as defined above, are prepared as abbreviated in Schemes 20.24a124b and 25. can.

Reaction formula 24 % formula % 61 60b (24b) 1a H2N Co2Et A uni-reaction formula 25 For details regarding the treatment of pyrazoles to substituted sulfonamide pyrazoles as abbreviated in Reaction formulas 18 to 25 above, , reaction formula 5, -7 (!'
, 10b, '11.12.13b113c and 14 and the references cited therein, and also European Patent Application 95.92.
5 teaches the synthesis of N-substituted pyrazole sulfonamides.

The prerequisite starting material 44 in Schemes 19.19b, 22a, 22b and 24a can be prepared in a number of ways. For example, alkylation of a protected hydrazine 63 with a substituted heterocycle 64 and subsequent hydrolysis produces compounds such as 44. This reaction is abbreviated in Reaction Scheme 26.

For more information on this type of rearrangement, see Organic Synthesis, 9.

2, 20B (1943); Ibid. 595 (1945) and OrganicRe
4.578 (1948).

On the other hand, compounds of Formula 44 can be prepared from the reaction of a suitable ketone with hydrazine as shown in Scheme 27. This method is particularly suitable where Q is a saturated heterocycle, such as Q-25 to Q-28, or a partially saturated heterocycle, such as Q-41 to Q-44.

Reaction formula 27 Regarding the description of the Wolf-Kishner reaction, see Todd (
Todd)'s Organic Reactions (Orga
nic Reactions)) 4.578 (1948
)checking.

The prerequisite starting material 60c in Scheme 25 can be prepared in several ways. For example, alkylation of a pyrazole with a suitably functionalized heterocycle QBr or QI as shown in Scheme 28 yields 600 is directly generated.

Reaction formula 28% Formula % N-alkylation of pyrazoles f1M is well known to experts in the art. On the other hand, pyrazoles can also be combined with halogenated heterocycles using a modification of the Ullmann reaction as shown in Schemes 29a and 29b. The υN-heterocycle can be preformed and added to the pyrazole sulfonamide by reaction 29b.

Reaction Formula 29 %Formula %() For further information on coupling using Pd or Cu catalysts, see S. Gronowuts and S. Reilfors, Chemica Scripta, 1
5, 157-161 (1978-1979) and A,
Minato, K.

Tamo, T-”Hayashi, K
.

Suzuki and M, Kumad
a) Tetrahedron Letters (Tetrahedr)
onLetters), Volume 22, 5! +19 (1981
) See i.

Other methods of synthesizing compounds such as 44 or 60c use heterocyclic amines such as 65. Soazotization and subsequent reduction of 65 directly provides 44 as shown in Scheme 50a. Hydran 44 full order 1.1,3
．． 60c by condensation with 5-tetraethoxyglonozone
(R2=H).

For details, see Jones, The Journal of American Chemical, 7-1, and S. R. Sandier, W. Karo. “Organic functional group production”, 2nd edition, 4
See pages 52-455, Academic Press Incorporated P1 New York, 1985.

Heterocyclic hydrazines can also be prepared from 66 by electrophilic substitution of active halodane as shown in Scheme 30b. Hyddinone 44 can then be converted to 61 as shown in Scheme 24a.

Reaction formula 50b Q-CI + NH2NH2→Q N HN Ht
Compounds such as 66-44 are well known in the literature and can be prepared by those skilled in the art. For an example of this common substitution reaction, see Nelson, P., and Potts, The Journal.
Op Organic Chemistry (J, Org, Ch.
See Em., ), 27.3245 (1962).

Heterocyclic amines of formula 6 in scheme 5 can be prepared by those skilled in the art by methods known in the literature or by simple modifications thereof.
4 (published on July 27, 198!1) and Breaker (
Braker) and other The Journal of the American Chemical Society (J, Am, C
Hem, Soe, ), 1947.69.5072 describes a process for the preparation of aminopyrimidines and triazines substituted by acetyl groups. Also South African Patent Application Nos. 8215045 and 8215671
is a haloalkyl or haloalkylthio group, such as especially 0CH2CH2F% 0CH2CF3 , S CF2
This paper describes a method for producing aminopyrimidines and triazines substituted with H, 0CF2H, and the like. South African Patent Application No. 85/7454C published 5 October 1985) discloses dichloroprobyl virimisones and triazines substituted by groups such as alkyl, haloalkyl, alkoxy, haloalkoxy, alkylamino, soalkylamino or alkoxyalkyl. It describes the synthesis method of the following types.

Furthermore, cyclopenta[2,5-'d ]]pyrimison-2-amines A is A-2;
d]pyrimidine-2-amines and 6,7-dihydro-5H-pyrano[2,3-d]virimiso/-2-amines in which A is A-5 are disclosed in European Patent Application No. 15.
, 683. Also,
furo[2,5-dlpyrimidine-2-
Amines 6 are described in European Patent Application No. 46.677.

Compounds of formula 6 in which A is A-5 are disclosed in U.S. Pat.
, 550.

Compounds of formula 6, where A is A-6, can be prepared by the method taught in European Patent Application No. 94,260 (published Nov. 16, 19B5).

Compounds of formula 6, where A is A-7, can be prepared by the method taught in European Patent Application No. 125.864 (published November 21, 1984).

Additionally, general methods for the preparation of aminopyrimidines and triazines are described in the following publications: ``1 Chemistry of Heterocyclic Compounds'', Interscience.
Series published by Papritschers Incorporated, New York and London, ``Pyrimidines'', D. J. Brown.
), Volume 16 of the same series, ``'s-)Ryazines and Derivatives'', E, M.

Smolin and L Labport (Rap)
F. C. Schaefer, U.S. Pat. No. 3,154.54, which describes the synthesis of triazines.
7 and R. Huffman and F.
, C. Schaefer's The Glossary Op Organic Chemistry (J. Org.

Chem, ), :? s, 1812 (1963).

Agriculturally suitable salts of compounds of formula I are also useful herbicides and can be prepared by a number of methods known in the art. It can be prepared by contacting with a solution of an alkali or alkaline earth metal salt (eg hydroxide, alkoxide or carbonate) having a specific anion. Quaternary amine salts can also be prepared by similar techniques.

Salts of compounds of formula (1) can also be prepared by exchanging one cation for another. Cation exchange is expressed by the formula■
salts of compounds (e.g. alkali or quaternary amine salts)
This can be carried out by directly contacting an aqueous solution of with a solution containing the cation to be exchanged. This method is most effective when the desired salt containing the exchanged cation is insoluble in water and can be separated by filtration.

The exchange is performed by filling an aqueous solution of a salt (e.g. an alkali metal or quaternary amine salt) of a compound of formula I with a cation exchange resin containing a cation intended to exchange the cation of the original salt. It can also be carried out by passing through a column and the desired product is all eluted from the column. This method is particularly useful when the desired salt is water soluble, such as potassium, sodium or calcium.

Acid addition salts useful in this invention are obtained by reacting a compound of Formula I with a suitable acid, such as p-toluenesulfonic acid, trichloroacetic acid, and the like.

The preparation of the compounds of the present invention is illustrated by the following examples.

Example 1 272 1,5-dimethyl-4-sulfonamide-5-
To a solution of methyl pyrazole carboxylate in 250 ml of ethanol was added all of the 292 hydrason hydrate salt. The solution was heated to reflux for 2 hours and then cooled to room temperature. On standing the product crystallized from solution to give the title compound 25.6f, mp 211-215°C.

Example 2 5.01 of 1,5-tmethyl-4-sulfonamide-5
-To a suspension of 50 rd of virazole hydrasod in ethanol was added in portions the entire solution of 1.4 F potassium hydroxide in 10-water. The solution was stirred for a further 15 minutes at room temperature and then 2.12 portions of carbon disulfide were added dropwise. 1 solution
Heat to reflux for 9 hours, then concentrate in vacuo and dissolve the fce1 solid residue in 7100 ml of water, acidify the solution with concentrated hydrochloric acid, collect the solid and air dry to 4.7F.
The title compound was obtained, melting point 243-245°C.

Example 5 Razolsulfonamide To a solution of 1.12 of 85 dipotassium hydroxide in 50 rnt of methanol was added 4.02 of 1,5-methyl-5-(2-mercapto-1,3,4-oxadiazi-
7-yl) pyrazole sulfonamide was added in portions, the solution was stirred for an additional 10 minutes, and then 2.679
of iodomethane was added dropwise. The solution was stirred at room temperature for 1 hour and under reflux for 1 hour. The reaction mixture was concentrated in vacuo and the resulting solid was washed with 100 ml of water and then air dried to give 3.3 F of the title compound. Melting point 1
56-1515℃.

Example 4 (Ethoxymethylene) Ethyl cyanacetate 19.52 to 1
One reactant was then added in portions to a 2.5 F solution of 2-hydrasonovirimison in 100-g of absolute ethanol.
Heated for -1/2 hour and cooled to collect all solids produced by filtration and washed with absolute ethanol. After air drying, the weight of the product is 22.6f, which is 9
Melted at 2-95°C.

Example 5 The product of Example 4 of 21,69 was dissolved at 0°C in 100 g of concentrated hydrochloric acid.

10ffi7! of 7.32 sodium nitrite to the resulting clear solution! A solution of was added over a period of 15 minutes at 0°C. The resulting suspension was stirred for an additional 50 minutes, then 1
One reaction in which cuprous chloride was added dropwise over 0 minutes to a 100% solution of hydrochloric acid was highly exothermic and was accompanied by rapid evolution of nitrogen. The suspension was then heated on a steam bath until the test for soazonium salts was negative. The contents of the flask were cooled, the pH of the suspension was adjusted with ammonium hydroxide and finally diluted with 100-water. The solids are filtered from the reactants by filtration through Celite,
The aqueous filtrate 'ii2007 was then washed with methylene chloride. After drying the organic solution over anhydrous sodium sulfate, a pale brown oil of 1Z42 was isolated after removal of the solvent by evaporation. Crude oil i250-400 mesh key cellke °
Flash chromatography on a column 60 using 1-1 hexanes/ethyl acetate as eluent for 7 ms.
The title compound was obtained with a melting point of 52-55[deg.]C in 14.2 y.

Example 6 Ethyl phosphate was dissolved in 1.42 methanol of sodium metal i50rnlV. After all the metals were dissolved, the solvent was removed in vacuo and the white powder was dissolved in all 65-DMF. 7.355' of benzyl mercaptan was added in portions and stirred for 60 minutes. The compound from Example 5 was added in portions over 5 minutes, producing a strong exotherm. After the reaction was pressed for a total of 60 minutes, the solvent was removed in vacuo and the residue was poured into ice water, the sticky material was dissolved in methylene chloride, and then the organic solution was washed with water. After removal of the solvent, the material was flash chromatographed on a Kiesselkeel 60 using 6-1 hexanes/ethyl acetate as eluent.

152 mixed esters with a melting point of 78-8 (1L5°C) were isolated.

Example 7 122 of the mixture i100 obtained from Example 6 was dissolved in glacial acetic acid and 1757 of water.

Cool the solution to 10°C and 13. All of the IF chlorine was added, the resulting suspension was stirred at room temperature for 2 hours, the 0 reaction was poured into ice water, and the aqueous solution was washed twice with ether, the FC0 organic solution was dried over anhydrous sodium sulfate, and strained. Straining gave a white solid. When added dropwise to a solution of 2.2 m/ml of ammonia and 100 rnt of THF, an exothermic reaction was added and diluted with water until all solids were dissolved.

Remove the organic layer and dry with anhydrous sodium sulfate.

Evaporation of the solvent gave a 6.02 yellow oil which was flash chromatographed on a Kieselker using 5-1 hexanes/ethyl acetate as eluent.

The ethyl ester of the title compound of 100 cm was isolated.

NMR (CDC13/TMS)” δa57-7.50
(m-5Hs pyridine ring and pyrazole 5-H)
:, 6.50 (b, 1.5H, NH proton); 4
．． 37Cq, 2H, 0CH2); 1.40 (t, 5H.

ethyl ester CH,).

350 ml of the methyl ester of the title compound was isolated.

Melting point 159-141°C.

NMR (CDCl2, DMSO-aa/TMS): δF
3.65-7.50 (m, 7H, pyridine ring,
Pyrazole 5-H and NH2: δ3.90(s, 5
H.

Ester OCHs) a Example 8 Methyl 3-(aminosulfonyl)-1-(2-pyridinyl)-1H-pyrazole-4-carboxylate and phenyl (4,6-dimethoxy-2-bilimisonyl)carbamate of 280η Dissolved in acetonitrile. α15m1 of 1,8-diazabicyclo[5,4,0
3 undecene was added and the reaction was stirred for 1 hour.

Solution f was diluted with 30 ml of ice water and acidified with concentrated hydrochloric acid. The separated solids were collected to give 260 ml of the title compound, mp 185-188°C.

Using the steps in Example fIJ 1-8, the techniques described in Scheme 1-60, or simple variations thereof, one skilled in the art can prepare the compounds in the table below.

= E E: 11:0:0: E E E E E E E 工= 工 Q E E E E E E E E = 工 (,' U (ME U () (ME (ME)
(Me (Me (7) Me (Me (Me) Noe.

E E E Q E E E E E E E E E E E E E E E01 01 0 01 Ql
01 (, X Ql (, I Ql ()
01 Ql (J (, l' (loe
E: I: E E E E E E E E E
E E E E = Gate + 111111111111111-Fist) 010101
0+0000C)00C)OIC)00100: E
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HC)t3Hq-C6(R-t“H)HC)I
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(CH3Q-13(R8"S-CH2-C6m45)
HCH3Q-13(R8-3-CH2-C6H5>
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− E E E E Eni.

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E E = E E E E N100
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:I::! ::! : E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E
E1, '1 work:
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'(701cy cy c cy o'
cy cy cy cy e e e e e = e e
= 工 工（J(J2C)C）CJo 2I
(JC2 (JCJL) : E E E 0 工:l::!::!: E E E
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E Engineering E E E E □.

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c; c; c; c; c; c; c&
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Emy Efu Ko: I :: i ::! : Engineering C):l: Engineering Engineering E E E E E E Enα E E E E E E E E E
E Nl o o CJ 2 o
a u u 2 u u 2 (J
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! : 工 工 :l:：l： 工 工 え え え
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α 0 α a α αE E E = E E E E E E E E E E E E (J
U21UCJCJCJCJ (JCJUU(JC)(J2
(JCJ Koko Q E E E E E E E E E E E E E
E e) Work Work Work Oe E E E E E E: I: E E E E E E E E C) Work ○ Work E E Work E E E Work E:! :
E: C: C engineering E α α 00 α α α
α a α α α α α α α ααe :f::! : E E81 CJ tJ C
J 2 CJ C) 2 U♂lEeninisue Otsu 8 ♂ Part 1 Engineering :I: E E :E:o Engineering Engineering dαα
a ααcy cy cy --H--hehehe n0 q < 1 <<<<<<<
<-1: Pebe Ku Supplementary♂? Il l I I I I I l l
l l :! :(J 工? 2″'1111110 (JOIII+, n え え え え nee 81ω (JC) ○ ri ■ 11 ■ ■Cl
N1 engineer: I: Suzuenie ee ee enii =
e E E E E E E E E E E E E E E E E E E E E E E E E E E E
E1 Dai:I::I: E-E-E-E-E-E-E-E-E-E-S”I
r41 Engineering :cOl::c E E E Engineering E
Useful preparations of the compounds can be prepared by conventional methods. They include powders, granules, tablets, solutions, emulsions, aqueous concentrates, concentrated emulsions, and the like. This species can be applied directly. Preparation for spraying: It can be bulked up in a noisy medium and used in spray volumes from a few pips/t to a few hundred feet. General Description 1 The product contains about 1% to 99% by weight of active ingredient, and about 0.1% to 20% surfactant, and b) about 5% to 20% solid or aqueous powder.
In particular, preparations containing at least 99% of at least one of these ingredients will contain approximately 1 part of these ingredients: 50 40-84
1-20 powder 1-95 70
-99 0-5 grains and tablets 1-95
5-99 0-15 High strength composition 90-99
0-10 0-2 Higher amounts of active ingredients than those listed may of course be present depending on the intended use and physical properties of the compound. A high proportion of surface-active to active ingredients is particularly desirable and is achieved by incorporation into the formulation or by mixing in a tank.

A typical solid diluent is Watkins
Written by (“l1andbook of In5ecti
cide Dust Diluents and Car
riers”, 2nd edition, Doland Books Co., Ltd.
rland Books, Caldwell, N.
J.), but other solids, both natural and synthetic, may also be used. Adsorptive diluents are also suitable for wettable powders and powder concentrates. Typical liquid diluents and solvents are described by Mατ5den, '5olve
nts guide'', 2nd edition, Interscience, N.Y., 1950. A solubility of 0.1% or less is suitable for concentrated suspensions; concentrated solutions are preferred. is stable to phase separation at 0°C.” McCutcheo7I/s
Deter-gttnts-and Emulsifi
ersΔannual”, 7/l/7 Red Publishing (A11ured publ, Corp, , N, J,)
, - and 5isely and Wood (V'
“ Encyclopedia o
f 5ur-f”ace, IC?ivgAgt,
nts”, Chemical Publishing Company (Chemical Pwbl)
, Co, Inc., N, Y.), 1964, displays surface activity and its recommended uses. All preparations may contain small amounts of additives to reduce foaming, caking, corrosion, microbial growth, etc. Preferably, each component should be approved by the US Environmental Protection Agency for its intended use.

Methods for producing such compositions are well known.

Solutions are prepared by simply mixing the components.

The finely divided solid composition is formed into rings by mixing 1 and usually grinding using a hammer mill or fluid energy mill. Suspension agents are manufactured by wet milling [
See, Litt-1er US Pat. No. 3.
No. 060.084]. Granules and tablets may be produced by spraying the active substance onto preformed granular carriers or by agglomeration methods.

Reference, J.E. Browning, “Agglomeration”, Chemica
l Engineering.

December 4 issue, p. 147 (1967), and Berry (
Perry), Chemical Engineering
i's l1and-book, 4th edition, McGraw-11i11.N, Y,
1973, pp. 8-59ff.

For further literature on the technique of preparation see, for example: 11, M. Louz, U.S. Pat. No. 1235,361, column 6, line 16 to column 7, line 19 and Examples 10-41.゜R, W, # Luckenbaugh
), U.S. Patent No. 3.309.192, column 5, 43
Line ~ Column 7, line 62 and Example 8.12.15.39.4
1.52.53.58.132.138-140.16
2~164.166.167.169~182゜H, Gys 侃 and E, Nusri (KTL舊-5
li), U.S. Pat. No. 2,891,855, column 3, 66.
Line to column 5, line 17 and Examples 1 to 4゜G, C, clear y y -? 7 (Klingman
), “1FlsedContral as a 5
John Wiley and 5ons.

Inc., N.Y.), 19.61, 81~
96 pages. “Fggd” by J. D. 7.
Control Handbook, 5th Edition, Blackwell Scientific Publishing
lications, Oxford), 1968, t.

Pages 1-103.

J. B. Buchanan X U.S. Patent 3,576, B54, 'April 27, 1971,
Lines 6 to 7 along j70 and Example 1-4.17.106
and 123-140, R.R. Shaffer, U.S. Pat.
．． 560,616.197'1 February 2, 5, lines 48 to 7, lines 26 and Examples 5-9 and 11-18, and Somers, E.
”, Chapter 6, Torson (Tor
In the following examples, all parts are by weight unless otherwise indicated.

Example 9 Irrigation agent amide 8o% sodium lignin sulfonate 2% synthetic amorphous silica 6% kaolinite
13% All of the above ingredients were mixed and ground in a hammer mill to give an average particle size of 20 microns or less. This material was remixed and packaged.

Example 10 Oily Suspension Agent Amide 25 Polyoxyethylene Rubitol Hexaoleate 5% Higher Aliphatic Hydrocarbon Oil 70% All of the above ingredients were ground together in a sand mill to reduce the solid particles to about 5 microns or less. Ta. The resulting suspension gold is preferably applied directly after being bulked up with oil or emulsified in water.

Example 11 Oil-Based Suspension Agent Xylene 59g of all of the above ingredients were then ground together in a sand mill to produce a t-film with particles essentially all below 3 microns.The product was used directly. It could also be bulked up with oil or emulsified in water.

Example 12 Solution Amide 5Tidimethylformamide 95% All of the above ingredients were combined and stirred to produce a solution that could be used for low volume applications.

Example 13 Concentrated Emulsion Xylene 91% The above ingredients were combined and stirred until the active ingredient was dissolved. Example 14: Aqueous suspension Calcium lignin sulfonate 5.0% Xanthan gum α 2% Paraformaldehyde 12% water
49.1%
The above ingredients were all slurried and milled together in a sand mill, ball mill or roller mill to produce particles essentially all dimensions less than 5 microns.

Example 15 Powder ethyl acid ester 10% athanoglugate 10% talc
The 80% active ingredient was blended with attapulguide and then passed through a hammer mill to produce essentially all particles under 200 microns. The ground concentrate was then blended with powdered talc until homogeneous.

Example 16 Granules Irrigation agent of Example 9 94% sugar
Six of the above ingredients were mixed using a rotary mixer or a fluidized bed mixer, and water was sprayed to form granules. When most of the material reached the desired size of 1.0-α42 bait (US Standard Sieve No. 18-40), all the particles were thrown out, dried, and sieved. Oversized materials were ground to the desired size. These particles contained 75.2% active ingredient.

Example 17 Granules Irrigation agent of Example 9 12.5% solids 50%
A slurry of water-friendly powder containing IJ-k was sprayed onto the surface of the Akpalguide particles in a double cone mixer. The particles were dried and packaged.

Example 18 Anhydrous Sodium Sulfate 10% Crude Calcium Lignosulfonate Sodium 5-Thialkylnaphthalene Sulfonate 1% The above ingredients were mixed, hammer milled, and then moistened with about 12 inches of water. This mixture was extruded into a cylinder with a total diameter of about 5 m111, and the entire cylinder was cut into tablets with a length of 3 W. It can be used directly after drying or by crushing the dry tablets using a No. 20 US standard sieve (opening α8).
4). American Standard Sieve No. 40 (
The particles that remained in the aperture α42 were packaged for use and circulated under the sieve.

Example 19 High Thickener Synthetic Amorphous Silica 5% The above ingredients were mixed and ground in a hammer mill to produce a high thickener that essentially all passed through a No. 50 US standard sieve (aperture α31D). This material was then used in various ways to produce preparations.

The results of application tests show that the compounds of the invention are active herbicides. They are used to pre-emergence weeds in areas where complete eradication of all vegetation is expected, such as around fuel storage tanks, around ammunition depots, industrial storage areas, parking lots, amphitheaters, around billboards, highways and railway areas. and/or exhibit broad utility for post-emergence control. Additionally, the compounds are useful for selectively controlling pre- and/or post-emergence weeds in crops such as rice, wheat and barley. Additionally, this compound is also useful for modifying the overall growth of plants.

The rate of use of the compounds of the invention will depend on their use as selective or systemic herbicides, the coexisting crop species, the weed species to be controlled, the weather and climate, the formulation chosen, the method of application, the amount of foliage present, etc. Determined by many factors including: Generally speaking, the compound should be used in an amount of about α010-2 Kv/ha. In this case, light soil and/or
or when used on soils with low organic matter content, when selectively controlling weeds, or when only short-term persistence is required, lower amounts in the above range are used.

The compounds of the invention can also be used in combination with other commercially available herbicides, such as those of the triazino, triazole, uracil, urea, amide, diphenyl ether, carbamate and bipyridium types.

The herbicidal properties of this compound have been demonstrated in a number of greenhouse tests. The test method and results are as follows.

Test A Djgitaria sp., Echinochloa crusgalli,
Oat (Ave naf a tua), Bromussecalfnus (Bromussecalfnus), Velvet leaf (Abutilontheophrasti)
, Morning Glory (Ipomoea sp.), Onamomi (
Seeds of Xantium gp-), sorghum, maize, soybean, cotton, sugar beet, rice, wheat and tubers of porphyry are planted in a growth medium and pre-germinated using chemicals dissolved in a solvent that is harmless to the plants. was processed. At the same time, these crops and weed species are grown in the soil7
It was also treated by foliar application. Plant height at the time of treatment is 2-181 cm
fC, treated and control plants were kept in the greenhouse for 16 days and all species were compared to the control;
Response to treatment was assessed visually. The evaluation method used was based on a scale from 0 (or no effect) to 10 (or &) or maximum effect. The accompanying letter symbols have the following meanings.

C = etiolation or turn: B = scorch; D = defoliation; E = germination inhibition; G = growth retardation; H = shadowing effect; U = abnormal pigmentation; Text = lateral bud stimulation; Dead disease; 6Y = abscessed bud or flower W
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Claims (1)

[Claims] 1. Formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼￥ I ￥ [In the formula, L is ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼￥L-1￥, ▲ Numerical formulas, chemical formulas, tables, etc. There are ▼￥L-2￥, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼￥L-3￥, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼￥L-4￥▲ There are mathematical formulas, chemical formulas, tables, etc. ▼￥L-5￥▲There are mathematical formulas, chemical formulas, tables, etc.▼￥
L-6￥ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼￥L
-7¥ and Q is selected from a saturated 5- or 6-membered ring containing one S or O heteroatom and one S, one O, 1-3 N and Q is optionally C_1-C_4 alkyl, C_1-C_4
haloalkyl, mercapto, benzylthio, halogen,
C_1-C_4 alkoxy, C_1-C_6 alkylthio, C_3-C_4 alkenyl, C_3-C_4 alkenylthio, C_3-C_4 alkynylthio, C_3-C
_4 haloalkenylthio, C_3-C_4 alkenyloxy, C_1-C_2 haloalkoxy, C_1-C_2
Haloalkylthio, C_2-C_4 cyanoalkylthio, C_3-C_6 alkoxycarbonylalkylthio,
C_2-C_5 alkoxyalkylthio or C_3-
Optionally substituted by one or more groups selected from C_3 acetylalkylthio, W is O or S, R is H or CH_3, R_1 is H, C_1-C_3 alkyl, C_1-C_3
haloalkyl or phenyl optionally substituted by Cl, NO_2, CH_3 or OCH_3, R_2 is H, Cl or CH_3, R_1_4 is H, C_1-C_4 alkyl, F, Cl,
Br, NO_2, C_1-C_3 haloalkylthio, C
_3-C_4 alkenyl, C_3-C_4 alkynyl,
CO_2R_1_7, C_1-C_3 alkylthio, C
_1-C_3 alkylsulfinyl, C_1-C_3 alkylsulfonyl or SO_2NR^I R^II, and R_1_5 and R_1_6 are independently H, C_1
-C_4 alkyl, C_2-C_4 alkoxyalkyl, C_1-C_3 haloalkylthio, C_1-C_3 haloalkoxy, C_1-C_3 alkoxy, C_1-C
_3 alkylthio, C_1-C_4 alkylsulfonyl, F, Cl, Br, CO_2R_1_7 or SO_2
NR^ I R^II, R^ I and R^II are independently C_1-C_3 alkyl, R_1_7 is C_1-C_3 alkyl, CH_2CH=
CH_2, CH_2C≡CH, CH_2CH_2Cl or CH_2CH_2OCH_3, A is ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼￥A-1￥, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼￥A-2￥, ▲ Mathematical formulas, chemical formulas , tables, etc. ▼￥A-3￥, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼￥A-4￥, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼￥A-5￥, ▲ Mathematical formulas, chemical formulas, tables, etc. etc. ▼￥A-6￥ or ▲
There are mathematical formulas, chemical formulas, tables, etc. ▼￥A-7￥, X
is H, C_1-C_4 alkyl, C_1-C_4 alkoxy, C_1-C_4 haloalkoxy, C_1-C_4
Haloalkyl, C_1-C_4 haloalkylthio, C_
1-C_4 alkylthio, halogen, C_2-C_5 alkoxyalkyl, C_2-C_5 alkoxyalkoxy, amino, C_1-C_3 alkylamino or di(
C_1-C_3 alkyl) amino, Y is H, C_1-C_4 alkyl, C_1-C_4 alkoxy, C_1-C_4 haloalkoxy, C_1-C_
4 haloalkylthio, C_1-C_4 alkylthio, C
_2-C_5 alkoxyalkyl, C_2-C_5 alkoxyalkoxy, amino, C_1-C_3 alkylamino, di(C_1-C_3 alkyl)amino, C_3-
C_4 alkenyloxy, C_3-C_4 alkynyloxy, C_2-C_3 alkylthioalkyl, C_2-
C_5 alkylsulfinyl alkyl, C_2-C_5
Alkylsulfonylalkyl, C_1-C_4 haloalkyl, C_3-C_5 cycloalkyl, C_2-C_4
Alkynyl, C(O)R_3, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc.▼ or N(OCH_3)CH_3, m is 2 or 3, L_1 and L_2 are independently O or S, and R_
3 is H or CH_3, R_4 and R_5 are independently C_1-C_2 alkyl, Z is CH or N, Y_1 is O or CH_2, X_1 is CH_3, OCH_3, OC_2H_5 or OCF_2H, Y_2 is H or CH_3, X_2 is CH_3, C_2H_5 or CH_2CF_
3, and Y_3 is OCH_3, OC_2H_5, SC
H_3, SC_2H_5, OCF_2H, SCF_2H
, CH_3 or C_2H_5, and X_3 is CH_
3 or OCH_3, and X_4 is CH_3, OCH
_3, OC_2H_5, CH_2OCH_3 or Cl
and Y_4 is CH_3, OCH_3 or OC_2H_5, provided that 1) when X is Cl, Br, F or I, Z is CH and Y is OCH_3, OC_2H_5, N
(OCH_3) CH_3, NHCH_3, N(CH_3
)_2, NH_2 or OCF_2H; 2) When X or Y is OCF_2H, Z is C
3) When W is S, R is H and A is A-1
and Y is CH_3, OCH_3, OC_2H_5, CH_2
OCH_3, C_2H_5, CF_3, SCH_3, O
CH_2CH=CH_2, OCH_2C≡CH, OCH
_2CH_2OCH_3, CH(OCH_3)_2 or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and 4) When the total number of carbons in X and Y is greater than 4, Q and R_2, R_1_4, R_1_
The total number of carbon atoms in 5 or R_1_6 is 10 or less, and 5) When L is L-5, L-6 or L-7, Q must be bonded to the pyrazole ring via a carbon atom. ] compounds and their agriculturally suitable salts. 2. Q is ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼￥Q-1￥, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼￥Q-2￥, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼￥Q-3 ¥, ▲There are mathematical formulas, chemical formulas, tables, etc.▼¥Q-4¥, ▲There are mathematical formulas, chemical formulas, tables, etc.▼¥Q-5¥, ▲There are mathematical formulas, chemical formulas, tables, etc.▼¥Q-6¥, ▲There are mathematical formulas, chemical formulas, tables, etc.▼￥Q
-7￥, ▲Mathematical formulas, chemical formulas, tables, etc.▼￥Q-8￥
, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼￥Q-9￥, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼￥Q-10￥, ▲ Mathematical formulas,
There are chemical formulas, tables, etc. ▼￥Q-11￥, ▲There are mathematical formulas, chemical formulas, tables, etc. ▼￥Q-12￥, ▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼￥Q-13￥, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼￥Q-14￥, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼￥Q-15￥, ▲ Mathematical formulas, chemical formulas, tables, etc. There are ▼￥Q-16￥, ▲There are mathematical formulas, chemical formulas, tables, etc.▼
￥Q-17￥, ▲There are mathematical formulas, chemical formulas, tables, etc.▼￥Q
-18 yen, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ ￥ Q-1
¥9, ▲There are mathematical formulas, chemical formulas, tables, etc.▼¥Q-20¥
, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼￥Q-21￥, ▲
There are mathematical formulas, chemical formulas, tables, etc. ▼￥Q-22￥, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼￥Q-23￥, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼￥Q-24￥, ▲ Mathematical formulas, There are chemical formulas, tables, etc. ▼￥Q-25￥, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼￥Q-26￥, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼￥Q-27￥, ▲ Mathematical formulas, chemical formulas, There are tables, etc. ▼￥Q-28￥, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼￥Q-29￥, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼￥
Q-30￥, ▲There are mathematical formulas, chemical formulas, tables, etc.▼￥Q-
¥31, ▲There are mathematical formulas, chemical formulas, tables, etc.▼¥Q-32
¥, ▲There are mathematical formulas, chemical formulas, tables, etc.▼¥Q-33¥,
▲ There are mathematical formulas, chemical formulas, tables, etc. ▼￥Q-34￥, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼￥Q-35￥, ▲ Mathematical formulas,
There are chemical formulas, tables, etc. ▼￥Q-36￥, ▲There are mathematical formulas, chemical formulas, tables, etc. ▼￥Q-37￥, ▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼￥Q-38￥, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼￥Q-39￥, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼￥Q-40￥, ▲ Mathematical formulas, chemical formulas, tables, etc. There are ▼￥Q-41￥, ▲There are mathematical formulas, chemical formulas, tables, etc.▼
￥Q-42￥, ▲There are mathematical formulas, chemical formulas, tables, etc.▼￥Q
-¥43, ▲There are mathematical formulas, chemical formulas, tables, etc.▼¥Q-4
4￥、▲There are mathematical formulas, chemical formulas, tables, etc.▼￥Q-45￥
, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼￥Q-46￥▲ There are mathematical formulas, chemical formulas, tables, etc. ▼￥￥Q-47￥ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼￥Q-48￥, R_6 and R_9 are independently H or CH_3, R_7 is H, CH_3 or Cl, R_8 is H, SH, CH_3, CH_2CH_3, S(
C_1-C_4 alkyl), S optionally substituted with 1 or 2 halogen atoms (C_3-C_4
alkenyl), S(C_3-C_4 alkynyl), OC
H_3, OCH_2CH_3, SCF_2H, CF_3
, or CN, CO_2R_4, OR_4 or C(
O) S (C_1-C_3 alkyl) substituted with CH_3, R_1_0 and R_1_1 are independently H, CH_3 or OCH_3, R_1_2 and R_1_3 are independently CH_3 or OCH_3, and R_1_3 is H, C_1 -C_3 alkyl or C_1
-C_3 alkylthio, and R_1_9 is C_1-C_3 alkyl or CH_2C
H=CH_2, but as a condition, when L is L-5, L-6 or L-7, Q is Q-25, Q-26, Q-27, Q-2
8, Q-41, Q-42, Q-43 or Q-44. 3. Compounds according to claim 2, wherein R is H and W is O. 4, R_1 is C_1-C_3 alkyl, Y is CH
_3, OCH_3, CH_2OCH_3, NHCH_3
, CH_2CH_3, C≡CH, C≡CCH_3, CH
(OCH_3)_2, CH(CH_3)_2 or cyclopropyl, and R_8 is H, SH, CH_3, SC
H_3 or OCH_3, R_1_4 is H, CH
_3, C_2H_5, CO_2CH_3, CO_2C_
2H_5, F, Cl, Br, SO_2CH_3, SO_
2C_2H_5, OCF_2H or SO_2N(CH
_3)_2, and R_1_5 and R_1_6
are independently H, CH_3, C_2H_5, CO_2CH
_3, CO_2C_2H_5, F, Cl, Br, SO_
Compounds according to claim 3, which are 2CH_3, SO_2C_2H_5, OCF_2H, or SO_2N(CH_3)_2. 5, X is CH_3, OCH_3, OC_2H_5, Cl
, Br or OCF_2H, claim 4
Compounds described in Section. 6. Compounds according to claim 5, wherein A is A-1. 7, L is L-1 and Q is Q-7, Q-13, Q
-15, Q-17, Q-18, Q-24, Q-31, Q
-32, Q-33, Q-37, Q-45, Q-46, Q
Compounds according to claim 6 selected from -47 and Q-48. 8, L is L-2 and Q is Q-7, Q-13, Q
-15, Q-17, Q-18, Q-24, Q-31, Q
-32, Q-33, Q-37, Q-45, Q-46, Q
Compounds according to claim 6 selected from -47 and Q-48. 9. Compounds according to claim 6, wherein L is L-7 and Q is Q-31. 10, N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1,5-dimethyl-3-[5
-(methylthio)-1,3,4-oxadiazole-2
-yl]-1H-pyrazole-4-sulfonamide. 11, N-[(4-methoxy-6-methyl-1,3,5
-triazin-2-yl)-aminocarbonyl]-1,
5-dimethyl-3-[5-(methylthio)-1,3,4
-Oxadiazol-2-yl]-1H-pyrazole-
Compounds according to claim 1, which are 4-sulfonamides. 12, N-[(4-chloro-6-methoxypyrimidine-
2-yl)aminocarbonyl]-1,3-dimethyl-5
-[5-(2-propenylthio)-1,3,4-oxadiazol-2-yl]-1H-pyrazole-4-sulfonamide, the compounds according to claim 1. 13, N-[4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-4-(5-methicapto-1,3
, 4-oxadiazol-2-yl)-1,5-dimethyl-1H-pyrazole-3-sulfonamide. 14,3-[[(4,6-dimethoxypyrimidine-2-
yl)aminocarbonyl]aminosulfonyl]-1-(
2-pyridinyl)-1H-pyrazole-4-carboxylic acid methyl ester. 15. An agriculturally suitable composition suitable for regulating undesirable plant growth, comprising an effective amount of a compound according to claim 1 and one of a surfactant, a solid or liquid diluent. thing. 16. An agriculturally suitable composition suitable for regulating undesirable plant growth, comprising an effective amount of a compound according to claim 2 and one of a surfactant, a solid or liquid diluent. thing. 17. An agriculturally suitable composition suitable for regulating undesirable plant growth, comprising an effective amount of a compound according to claim 3 and one of a surfactant, a solid or liquid diluent. thing. 18. An agriculturally suitable composition suitable for regulating undesirable plant growth, comprising an effective amount of a compound according to claim 4 and one of a surfactant, a solid or liquid diluent. thing. 19. An agriculturally suitable composition suitable for regulating undesirable plant growth, comprising an effective amount of a compound according to claim 5 and one of a surfactant, a solid or liquid diluent. thing. 20. An agriculturally suitable composition suitable for regulating undesirable plant growth, comprising an effective amount of a compound according to claim 6 and one of a surfactant, a solid or liquid diluent. thing. 21. An agriculturally suitable composition suitable for regulating undesirable plant growth, comprising an effective amount of a compound according to claim 7 and one of a surfactant, a solid or liquid diluent. thing. 22. An agriculturally suitable composition suitable for regulating undesirable plant growth, comprising an effective amount of a compound according to claim 8 and one of a surfactant, a solid or liquid diluent. thing. 23. An agriculturally suitable composition suitable for regulating undesirable plant growth, comprising an effective amount of a compound according to claim 9 and one of a surfactant, a solid or liquid diluent. thing. 24. An agriculturally suitable composition suitable for regulating undesirable plant growth, comprising an effective amount of a compound according to claim 10 and one of a surfactant, a solid or liquid diluent. thing. 25. An agriculturally suitable composition suitable for regulating undesirable plant growth, comprising an effective amount of a compound according to claim 11 and one of a surfactant, a solid or liquid diluent. thing. 26. An agriculturally suitable composition suitable for regulating undesirable plant growth, comprising an effective amount of a compound according to claim 12 and one of a surfactant, a solid or liquid diluent. thing. 27. An agriculturally suitable composition suitable for regulating undesirable plant growth, comprising an effective amount of a compound according to claim 13 and one of a surfactant, a solid or liquid diluent. thing. 28. An agriculturally suitable composition suitable for regulating undesirable plant growth, comprising an effective amount of a compound according to claim 14 and one of a surfactant, a solid or liquid diluent. thing. 29. An agriculturally suitable composition suitable for regulating undesirable plant growth, comprising an effective amount of a compound according to claim 15 and one of a surfactant, a solid or liquid diluent. thing. 30. A method for regulating undesirable plant growth, comprising applying an effective amount of a compound according to claim 1 to the site to be protected. 31. A method for regulating undesirable plant growth, which comprises applying an effective amount of a compound according to claim 2 to the site to be protected. 32. A method for regulating undesirable plant growth, which comprises applying an effective amount of a compound according to claim 3 to the site to be protected. 33. A method for regulating undesirable plant growth, which comprises applying an effective amount of a compound according to claim 4 to the site to be protected. 34. A method for regulating undesirable plant growth, which comprises applying an effective amount of a compound according to claim 5 to the site to be protected. 35. A method for regulating undesirable plant growth, which comprises applying an effective amount of a compound according to claim 6 to the site to be protected. 36. A method for controlling undesirable plant growth, which comprises applying an effective amount of a compound according to claim 7 to the site to be protected. 37. A method for regulating undesirable plant growth, comprising applying an effective amount of a compound according to claim 8 to the site to be protected. 38. A method for controlling undesirable plant growth, which comprises applying an effective amount of a compound according to claim 9 to the site to be protected. 39. A method for regulating undesirable plant growth, comprising applying an effective amount of a compound according to claim 10 to the site to be protected. 40. A method for regulating undesirable plant growth, comprising applying an effective amount of a compound according to claim 11 to the site to be protected. 41. A method for regulating undesirable plant growth, which comprises applying an effective amount of a compound according to claim 12 to the site to be protected. 42. A method for regulating undesirable plant growth, which comprises applying an effective amount of a compound according to claim 13 to the site to be protected. 43. A method for regulating undesirable plant growth, which comprises applying an effective amount of a compound according to claim 14 to the site to be protected. 44. A method for regulating undesirable plant growth, comprising applying an effective amount of a compound according to claim 15 to the site to be protected.