CN87107320A - Herbicidal pyridine sulfonylureas - Google Patents
Herbicidal pyridine sulfonylureas Download PDFInfo
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- CN87107320A CN87107320A CN87107320.XA CN87107320A CN87107320A CN 87107320 A CN87107320 A CN 87107320A CN 87107320 A CN87107320 A CN 87107320A CN 87107320 A CN87107320 A CN 87107320A
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- och
- alkyl
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- compound
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims description 30
- 229940100389 Sulfonylurea Drugs 0.000 title claims description 5
- 230000002363 herbicidal effect Effects 0.000 title description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title description 9
- 229910005965 SO 2 Inorganic materials 0.000 claims description 1085
- -1 sulphinyl Chemical group 0.000 claims description 238
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- 229940124530 sulfonamide Drugs 0.000 claims description 71
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- UNAHYJYOSSSJHH-UHFFFAOYSA-N oryzalin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(N)(=O)=O)C=C1[N+]([O-])=O UNAHYJYOSSSJHH-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 description 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011819 refractory material Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- YRNIQASZWVFCJP-UHFFFAOYSA-N s-ethyl carbamothioate Chemical compound CCSC(N)=O YRNIQASZWVFCJP-UHFFFAOYSA-N 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 229910002029 synthetic silica gel Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000036346 tooth eruption Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The present invention relates to pyridylsulfonylurea herbicides which are highly active as preemergent and postemergent herbicides.
Description
The application's pyridine sulfonylurea shows very high activity as teething is preceding with the back weedkiller that sprouts.Especially, it is safe many being proved for corn being arranged in these weedkiller.
EP-A-13, the 480 sulfanilamide (SN) weedkiller that disclose, its general formula is
R wherein
1Be H, Cl, Br, F, C
1-C
4Alkyl, C
1-C
4Alkoxyl group, C
1-C
4Alkylthio, NO
2Or CO
2R
5
The U.S.4 of issue on March 6th, 1984, the U.S.4 of issue on June 11st, 435,206 and 1985,522,645 disclose on 3 by R
1The 2-pyridine sulfonylurea that replaces, wherein R
1Be H, Cl, Br, F, C
1-C
4Alkyl, C
1-C
4Alkoxyl group, C
1-C
4Alkylthio, NO
2, CF
3, CO
2R
5Or SO
2NR
6R
7
U.S.4,339, the 267 sulfanilamide (SN) weedkiller that disclose, its general formula is
R wherein
4Be H, Cl, Br, F, C
1-C
4Alkyl, C
1-C
4Alkoxyl group, NO
2, CO
2R
6Or SR
13
EP-A-30, the 433 sulfanilamide (SN) weedkiller that disclose, its general formula is
Wherein
X is H;
R
14Be H or CH
3;
R
3Be H, F, Cl, Br, CH
3, NO
2, CO
2R
11Or S(O) nR
12
U.S.4,456, the 469 sulfanilamide (SN) weedkiller that disclose, its general formula is
Wherein R is C
1-C
6Alkyl, C
3-C
6Alkenyl, C
2-C
4Alkoxyalkyl, C
5-C
6Cycloalkyl, R ' OCH
2CH
2OCH
2, R ' OCH
2CH
2OCH
2CH
2,
CF
3,
CF
3CH
2, HGLCCF
2Or HCF
2;
Z is H, F, Cl, Br, CH
3, OCH
3, or SCH
3
U.S.4,487, the 626 sulfanilamide (SN) weedkiller that disclose, its general formula is
Wherein A is
R
2Be H, F, Cl, Br, C
1-C
4Alkyl, C
1-C
4Alkoxyl group, NO
2, CO
2R
15, S(O) mR
16, SO
2NR
18R
19Or SO
2N(OCH
3) CH
3
U.S.4,421, the 550 sulfanilamide (SN) weedkiller that disclose, general formula is
R
16Be H, C
1-C
4Alkyl, C
1-C
4Alkoxyl group, F, Cl, Br, CF
3, CO
2R
20, SO
2NR
10R
11, SO
2N(OCH
3) CH
3Or S(O) nR
13
U.S.4,496,392 disclose the sulfanilamide (SN) weedkiller, and its general formula is
R wherein
3Be Cl, SO
2CH
3Or SO
2N(CH
3)
2
EP-A-84, the 224 sulfanilamide (SN) weedkiller that disclose, its general formula is
Wherein A is
R
16Be H, C
1-C
4Alkyl, C
1-C
4Alkoxyl group, F, Cl, Br, CF
3, CO
2R
9, SO
2NR
10R
11, SO
2N(OCH
3) CH
3Or S(O) nR
13
EP-A-125, the 846 sulfanilamide (SN) weedkiller that disclose, its general formula is
R
3Be Cl, SO
2CH
3, SO
2N(CH
3)
2, OCH
3, NO
2Or N(CH
3)
2
EP-A-155,767 disclose the sulfanilamide (SN) weedkiller, and its general formula is
R
5Be H, CH
3, Cl, Br, CO
2R
15, C(O) NR
16R
17SO
2NR
16R
17, SO
2N(OCH
3) CH
3, SO
2R
18Or NO
2
EP-A-161, the 905 sulfanilamide (SN) weedkiller that disclose, its general formula is
R wherein
4Be CH
3, CH
2CH
3, OCH
3, OCH
2CH
3, F, Cl, Br, SO
2NR
16R
17, SO
2N(OCH
3) CH
3, S(O) nR
19, C
3-C
4Alkenyloxy or C
3-C
4Alkynyloxy group.
EP-A-164, the 269 sulfanilamide (SN) weedkiller that disclose, its general formula is
R wherein
4Be CH
3, CH
2CH
3, OCH
3, OCH
2CH
3, F, Cl, Br, SO
2NR
11R
12, SO
2N(OCH
3) CH
3Or S(O) nR
13
EP-A-171, the 286 sulfanilamide (SN) weedkiller that disclose, its general formula is
R wherein
4Be CH
3, CH
2CH
3, OCH
3, OCH
2CH
3, F, Cl, Br, SONR
18R
19, SO
2N(OCH
3) CH
3, S(O) nR C
3-C
4Alkenyloxy, CH
2OCH
3Or CH
2OCH
2CH
3
The sulfanilamide (SN) weedkiller that the south african patent application 83/4305 of announcing December 14 nineteen eighty-three discloses, its general formula is
R wherein
2Be H, C
1-C
3Alkyl, C
1-C
3Haloalkyl, halogen, NO
2, C
1-C
3Alkoxyl group, C(W) R
8, SO
2NR
6R
7, S(O) n-C
1-C
3Alkyl or C(O) R
9;
R
3Be H, fontanel element, C
1-C
3Alkyl, OCH
3, NO
2Or CF
3;
R
5Be H, NO
2, F, Cl, Br, CH
3, CF
3, S(O) nC
1-C
3Alkyl, C(O) C
1-C
4Alkoxyl group or C
1-C
3Alkoxyl group;
Y is O or S.
The sulfanilamide (SN) weedkiller that the south african patent application 83/6639 of announcing on March 8th, 1984 discloses, its general formula is
Wherein A is C
3-C
6Alkynyl free radical, C
1-C
6Alkyl diradical, they can be by halogen, C
1-C
4Alkoxyl group, C
1-C
4Alkylthio, C
1-C
4Alkyl sulphinyl, C
1-C
4Alkyl sulphonyl, C
1-C
4Halogenated alkoxy, C
1-C
4Haloalkyl thio, C
1-C
4Haloalkyl sulfinyl or C
1-C
4Halogenated alkyl sulfonyl replaces, or unsubstituted or as C
1-C
6The C that alkyl replaces
2-C
4The alkenyl free radical, or replace or unsubstituted phenyl free radical by following groups: halogen, cyano group, nitro, C
1-C
4Alkyl, C
1-C
4Haloalkyl ,-X-C
1-C
4Alkyl, C
1-C
4Carbalkoxy, amino, list or two (C
1-C
4Alkyl) amino, formamyl, list or two (C
1-C
4Alkyl) formamyl, sulphonamide, list or two (C
1-C
4Alkyl) sulfamyl;
R
1Be hydrogen, halogen, C
1-C
4Alkyl, C
1-C
4Alkoxyl group, C
1-C
4Haloalkyl, C
1-C
4Halogenated alkoxy, C
2-C
5Alkoxyalkoxy group, C
1-C
5Alkylthio, C
1-C
5Alkyl sulphinyl or C
1-C
6Alkyl sulphonyl;
X is O, S, SO or SO
2
U.S.4,518,776 disclose the herbicidal preparation method of sulfanilamide (SN), and its general formula is
R wherein
1Part is S(O) nC
1-C
4Alkyl, SO
2-two-C
1-C
4Alkylamino or CO
2-C
1-C
2Alkyl;
R
2Be H, halogen, CF
3, NO
2, C
1-C
4Alkyl or C
1-C
4Alkoxyl group.
This patent discloses some compound of the present invention prevailingly, but any one is not proposed claim.
The EP-A-101 that on February 29th, 1984 announced, 670 disclose the herbicidal preparation method of sulfanilamide (SN), and its general formula is
R wherein
1Be Q-C
1-C
4Alkyl, SO
2-two-C
1-C
4Alkylamino or CO
2-C
1-C
4Alkyl;
Q is S or S(O) n;
R
2Be H, halogen, CF
3, NO
2, C
1-C
4Alkyl or C
1-C
4Alkoxyl group.
This application discloses some compound among the present invention prevailingly.
U.S.4,521,597 disclose the herbicidal preparation method of sulfanilamide (SN), and its general formula is
R wherein
3Be H, F, Cl, Br, NO
2, OCH
3Or CF
3;
R
5Be S(O) mC
1-C
5Alkyl, SO
2NR
8R
9Or COR
7;
R
6Be H, F, CH
3Or OCH
3
This patent discloses some compound among the present invention prevailingly, but any one is not proposed claim.
The EP-A-184 that on June 11st, 1986 announced, 385 disclose the following compound of selectivity inhibition weeds in tomato and meadow.
U.S.S.N.874,307 disclose neighbour-alkyl-carbonyl-herbicide containing mainly pyridine sulfonylurea.
U.S.S.N.943,137 disclose the herbicide containing mainly pyridine sulfonylurea that the ortho position replaces.
The application relate to the formula I novel cpd, be applicable to agricultural contain this type of compound compositions and with them as the method preceding and/or that sprout back weedkiller or plant-growth regulator use of sprouting, and they are suitable for the salt of agricultural use.
Wherein
J is
R is H or CH
3;
W is O or S;
R
1Be Rf or Rg;
Rf is H, C
1-C
3Alkyl, C
1-C
3Haloalkyl, halogen, NO
2, C
1-C
3Alkoxyl group, C
1-C
3Alkylthio or CN;
R
9Be C
1-C
3Haloalkyl, C
2-C
3Alkyl, cyclopropyl, by C
1-C
3Alkoxyl group, OH, C
1-C
2The C that alkylthio or CN replace
1-C
3Alkyl, CN, W
2R
11, amino, C
1-C
3Alkylamino or C
1-C
3Dialkyl amido;
R
2Be C
1-C
4Alkyl sulphinyl, C
1-C
4Alkyl sulphonyl, C
3-C
5Cycloalkyl sulfo-, C
3-C
5Cycloalkyl sulfinyl, C
3-C
5Ring-alkyl sulphonyl, SO
2NH
2, SO
2NRd Re, SO
2NR
7' R
8, SO
2NR
7R
8, OSO
2R
8, SO
2OR
8, N
3, P(W
1) (OC
1-C
2Alkyl)
2, CN, CO
2R
9, CO
2R
9', CH
2F, CH
2F, CF
2H, CH
2Cl, CCl
2H or C
2-C
4Haloalkyl;
R
3Be C
1-C
4Alkyl sulphinyl, C
3-C
5Cycloalkyl sulfo-, C
3-C
5Cycloalkyl sulfinyl, C
3-C
4Naphthene sulfamide base, SO
2NH
2, SO
2NRd Re, SO
2NR
7R
8, SO
2NR
7' R
8, OSO
2R
8, SO
2OR
8, N
3, P(W
1) (OC
1-C
2Alkyl)
2, CN, CO
2R
9, CO
2R
9' or C
1-C
4Haloalkyl;
R
4Be C
1-C
4Alkyl sulphinyl, C
3-C
5Cycloalkyl sulfo-, C
3-C
5Cycloalkyl sulfinyl, C
3-C
4Naphthene sulfamide base, SO
2NH
2, SO
2NRd Re, SO
2NR
7R
8, OSO
2R
8, SO
2OR
8, N
3, P(W
1) (OC
1-C
2Alkyl)
2, CN, CO
2R
9Or C
1-C
4Haloalkyl;
R
5Be C
1-C
4Alkyl sulphinyl, C
1-C
4Alkyl sulphonyl, C
3-C
5Cycloalkyl sulfo-, C
3-C
5Cycloalkyl sulfinyl, C
3-C
5Naphthene sulfamide base, SO
2NH
2, SO
2NRd Re, SO
2NR
7R
8, OSO
2R
8, SO
2OR
8, N
3, P(W
1) (OC
1-C
2Alkyl)
2, CN, CO
2R
9Or C
1-C
4Haloalkyl;
R
6Be C
1-C
4Alkylthio, C
1-C
4Alkyl sulphinyl, C
1-C
4Haloalkyl thio, C
1-C
4Haloalkyl sulfinyl, C
1-C
4Halogenated alkyl sulfonyl, C
3-C
4Alkenyl sulfo-, C
3-C
4Alkenyl sulfinyl, C
3-C
4Alkenyl alkylsulfonyl, C
3-C
4Alkynyl sulfo-, C
3-C
4Alkynyl sulfinyl, C
3-C
4Alkynyl alkylsulfonyl, C
3-C
5Cycloalkyl sulfo-, C
3-C
5Cycloalkyl sulfinyl, C
3-C
5Naphthene sulfamide base, SO
2NRd Re, SO
2NR
7R
8, OSO
2R
8, SO
2OR
8, N
3, P(W
1) (OC
1-C
2Alkyl)
2, CN, CO
2R
9Or C
1-C
4Haloalkyl;
R
7Be H, C
2-C
3Cyano group alkyl, C
3-C
4Alkenyl or C
3-C
4Alkynyl;
R
7' be C
1-C
4Alkyl;
R
8Be C
1-C
4Alkyl, C
1-C
4Haloalkyl, C
3-C
4Alkenyl, C
3-C
4Alkynyl, C
2-C
4Alkoxyalkyl or cyclopropyl; Or
R
7And R
8Can connect together becomes-(CH
2)
3-,-(CH
2)
4-,-(CH
2)
5-or-CH
2CH
2OCH
2CH
2-;
R
9Be CH
2CH
2R
10, CH
2CF
3, C
3-C
4Haloalkyl, C
3-C
4Alkynyl, C
2-C
4Alkyl-thio-alkyl, C
3-C
5Cycloalkyl or C
4-C
7Cycloalkylalkyl;
R
9' be C
1-C
4Alkyl, C
3-C
4Alkenyl, CH
2CH
2Cl, CH
2CH
2Br, CH
2CH
2OCH
3Or CH
2CH
2OC
2H
5;
R
10Be OH, F, CN, OSO
2(C
1-C
3Alkyl) or OSO
2(C
1-C
3Haloalkyl);
R
11Be C
1-C
3Alkyl, C
1-C
3Haloalkyl, C
3-C
4Alkenyl or C
3-C
4Alkynyl;
W
1Be O or S;
W
2Be O or S;
A is
X is H, C
1-C
4Alkyl, C
1-C
4Alkoxyl group, C
2-C
4Halogenated alkoxy, C
1-C
4Haloalkyl, C
2-C
4Haloalkyl thio, C
1-C
4Alkylthio, halogen, C
2-C
5Alkoxyalkyl, C
2-C
5Alkoxyl group alkoxyl group, amino, C
1-C
3Alkylamino or two (C
1-C
3Alkyl) amino;
Y is H, C
1-C
4Alkyl, C
1-C
4Alkoxyl group, C
2-C
4Halogenated alkoxy, C
2-C
4Haloalkyl thio, C
1-C
4Alkylthio, C
2-C
5Alkoxyalkyl, C
2-C
5Alkoxyl group alkoxyl group, amino, C
1-C
3Alkylamino, two (C
1-C
3Alkyl) amino, C
3-C
4Alkenyloxy, C
3-C
4Alkynyloxy group, C
2-C
5Alkyl-thio-alkyl, C
2-C
5Alkyl sulphinyl alkyl, C
2-C
5Alkyl sulphonyl alkyl, C
1-C
4Haloalkyl, C
2-C
4Alkynyl, C
3-C
5Cycloalkyl, azido-,
Or N(OCH
3) CH
3;
M is 2 or 3;
Q
1And Q
2Be respectively O or S;
Ra is H or C
1-C
3Alkyl;
Rb and Rc are respectively C
1-C
3Alkyl;
Rd is H or C
1-C
2Alkyl;
Re is C
1-C
2Alkoxyl group;
Z is CH, N, CCH
3, CC
2H
5, CCl or CBr;
Y
1Be O or CH
2;
X
1Be CH
3, OCH
3, OC
2H
5Or OCF
2H;
X
2Be CH
3, C
2H
5Or CH
2CF
3;
Y
2Be OCH
3, OC
2H
5, SCH
3, SC
2H
5, CH
3Or CH
2CH
3;
X
3Be CH
3Or OCH
3;
Y
3Be H or CH
3;
X
4Be CH
3, OCH
3, OC
2H
5, CH
2OCH
3Or Cl;
Y
4Be CH
3, OCH
3, OC
2H
5Or Cl;
Suppose
1) if X is a halogen, then Z is CH, and Y is OCH
3, OC
2H
5, NH
2, NHCH
3, N(CH
3)
2Or N(OCH
3) CH
3;
2) if W is S, then R is H, and A is A-1, and Z is CH or N, and Y is CH
3, OCH
3, OC
2H
5, CH
2OCH
3, C
2H
5, CF
3, SCH
3, OCH
2CH=CH
2, OCH
2C ≡ CH, OCH
2CH
2OCH
3, CH(OCH
3)
2Or
;
3) if the total number of carbon atoms of X and Y greater than 4, R then
1, R
2, R
3, R
4, R
5Or R
6Carbonatoms add up to and to be less than or equal to 6;
4) if J is J-1, R
2Be C
1-C
4Alkyl sulphonyl, SO
2NRd Re, SO
2NR
7' R
8Or CO
2R
9'; If or J is J-2, R
3Be CF
3, SO
2NRd Re, SO
2NR
7' R
8Or CO
2R
9', then Y is not C
2-C
5Alkyl-thio-alkyl, C
2-C
5Alkyl sulphinyl alkyl, C
2-C
5The alkyl sulphonyl alkyl,
5) if J is J-2 or J-3, R
3Or R
4Be C
1-C
4Alkyl sulphinyl, then X and Y are not NH
2Or NHCH
3;
6) if J is J-2, R
3Be C
1-C
4Alkyl sulphinyl or SO
2NRd Re, or R
7Be H, then X and Y are not C
2-C
4Halogenated alkoxy;
7) if J is J-5, R then
7Not H and R
6Not SO
2NRd Re;
8) if J is J-2 and R
3Be SO
2NH
2Or SO
2NRd Re, or R
7Be H, then X is not an iodine;
9) if J is J-2 and R
7Be H or R
3Be SO
2NRd Re, then Y is not C
2-C
4Alkynyl;
10) X
4And Y
4Not Cl simultaneously;
11) if J is J-1, J-2, J-3, J-4 and A is A-5, then Rf is not H;
12) if J is J-1 or J-2, then A is not A-6;
13) if J is J-1 and A is A-7, R then
2Not C
1-C
4Alkyl sulphonyl;
14) if R
2Or R
3Be CO
2R
9' or SO
2NR
7' R
8, R then
1Be Rg; If R
2Or R
3Not CO
2R
9' or SO
2NR
1' R
8, R then
1Be Rf;
15) if J is J-2 and R
1Be adjacent to the sulfonylurea bridged bond, then Rg is C
1-C
3Haloalkyl, C
2-C
3Alkyl, cyclopropyl, CN, W
2R
11, amino, C
1-C
3Alkylamino or C
1-C
3Dialkyl amido.
In above-mentioned definition, noun " alkyl " all is meant straight chain and branched-chain alkyl, for example methyl, ethyl, n-propyl, sec.-propyl or different butyl isomer no matter be to use separately or be used for compound word as " alkylthio " or " haloalkyl ".
Alkoxyl group is meant methoxyl group, oxyethyl group, positive propoxy or isopropoxy.
Alkenyl is meant straight or branched alkene, for example 1-propenyl, 2-propenyl, 3-propenyl and different butenyl isomer.
Alkynyl is meant straight or branched alkynes, for example ethynyl, 1-proyl, 2-propynyl and different butynyl isomer.
Alkyl sulphonyl is meant methyl sulphonyl, ethylsulfonyl and different sulfonyl propyl base and butyl alkylsulfonyl isomer.
Cycloalkyl is meant cyclopropyl, cyclobutyl and cyclopentyl.
Noun " halogen " though be independent or compound word as " haloalkyl " in, all be meant fluorine, chlorine, bromine or iodine.Further, if be used in compound word as in " haloalkyl ", described alkyl can be by partially halogenated or with can identically replacing fully by different halogen atoms.The example of haloalkyl comprises CH
2CH
2F, CF
2CF
3And CH
2CHFCl.Equally, this definition also is applicable to halogenated alkoxy and haloalkyl thio.
The total number of carbon atoms in the substituting group represents that with the Ci-Cj prefix wherein i and j are 1 to 5 numerals.For example, C
1-C
3Alkyl sulfonyl basis representation methyl sulphonyl is to sulfonyl propyl base, C
2Alkoxyalkoxy group is represented OCH
2OCH
3, C
2The cyano group alkyl is represented CH
2CN, C
3The cyano group alkyl is represented CH
2CH
2CN and CH(CN) CH
3Preferred compound
Preferred compound is as follows in order to be easier to synthetic and/or better deweeding effect:
1. the compound of formula I, wherein
X is C
1-C
2Alkyl, C
1-C
2Alkoxyl group, Cl, F, Br, I, CH
2F, CF
3, OCH
2CH
2F, OCH
2CHF
2, OCH
2CF
3, CH
2Cl or CH
2Br;
Y is H, C
1-C
2Alkyl, C
1-C
2Alkoxyl group, CH
2OCH
3, CH
2OCH
2CH
3, NHCH
3, N(OCH
3) CH
3, N(CH
3)
2, CF
3, SCH
3, OCH
2CH=CH
2, OCH
2C ≡ CH, OCH
2CH
2OCH
3,
CH
2SCH
3, cyclopropyl, C ≡ CH or C ≡ CCH
3;
Ra is H or CH
3;
Z is CH or N.
2.1 in preferred compound, wherein
W is O;
Rf is H, CH
3, C
1Haloalkyl, halogen or OCH
3;
Rg is C
1-C
2Haloalkyl, ethyl, W
2R
11, CH
2OCH
3, CH
2SCH
3, CH
2CN, C
1-C
2Alkylamino or N(CH
3)
2;
R
2Be C
1-C
4Alkyl sulphinyl, C
1-C
4Alkyl sulphonyl, SO
2NH
2, SO
2NRd Re, SO
2NR
7R
8, SO
2NR
7' R
8, OSO
2R
8, SO
2OR
8, N
3, P(W
1) (OC
1-C
2Alkyl)
2, CN, CO
2R
9, CO
2R
9', CHF
2, CF
2H, CH
2Cl, CCl
2H or C
2-C
4Haloalkyl;
R
3Be C
1-C
4Alkyl sulphinyl, SO
2NH
2, SO
2NRd Re, SO
2R
7R
8, SO
2NR
7' R
8, OSO
2R
8, SO
2OR
8, N
3, P(W
1) (OC
1-C
2Alkyl)
2, CN, CO
2R
9, CO
2R
9' or C
1-C
4Haloalkyl;
R
4Be C
1-C
4Alkyl sulphinyl, SO
2NH
2, SO
2N(OCH
3) CH
3, SO
2NR
7R
8, OSO
2R
8, SO
2OR
8N
3, P(W
1) (OC
1-C
2Alkyl)
2, CN, CO
2R
9Or C
1-C
4Haloalkyl;
R
5Be C
1-C
4Alkyl sulphinyl, C
1-C
4Alkyl sulphonyl, SO
2NH
2, SO
2N(OCH
3) CH
3, SO
2NR
7R
8, OSO
2R
8, SO
2OR
8, N
3, P(W
1) (OC
1-C
2Alkyl)
2, CN, CO
2R
9Or C
1-C
4Haloalkyl;
R
6Be C
1-C
4Alkylthio, C
1-C
4Alkyl sulphinyl, C
1-C
4Haloalkyl thio, C
1-C
4Haloalkyl sulfinyl, C
1-C
4Halogenated alkyl sulfonyl, C
3-C
4Alkenyl sulfo-, C
3-C
4Alkenyl sulfinyl, C
3-C
4Alkenyl alkylsulfonyl, C
3-C
4Alkynyl sulfo-, C
3-C
4Alkynyl sulfinyl, C
3-C
4Alkynyl alkylsulfonyl, SO
2N(OCH
3) CH
3, SO
2NR
7R
8, OSO
2R
8, SO
2OR
8, N
3, P(W
1) (OC
1-C
2Alkyl)
2, CN, CO
2R
9Or C
1-C
4Haloalkyl;
R
7Be H, C
2-C
3Cyano group alkyl, C
3-C
4Alkenyl or C
3-C
4Alkynyl;
R
8Be C
1-C
4Alkyl, C
1-C
4Haloalkyl, C
3-C
4Alkenyl, C
3-C
4Alkynyl, C
2-C
4Alkoxyalkyl or cyclopropyl;
R
11Be C
1-C
3Alkyl, C
1-C
2Haloalkyl, allyl group or propargyl.
3.2 in preferred compound, wherein J is J-1.
4.2 in preferred compound, wherein J is J-2.
5.2 in preferred compound, wherein J is J-3.
6.2 in preferred compound, wherein J is J-4.
7.2 in preferred compound, wherein J is J-5.
8.3 in preferred compound, wherein
R
7Be H, C
2-C
3Cyano group alkyl, allyl group or propargyl;
R
7' be C
1-C
3Alkyl;
R
8Be C
1-C
3Alkyl, allyl group, propargyl or cyclopropyl;
R
9Be CH
2CH
2R
10, CH
2CH
2SCH
3, propargyl or cyclopropyl methyl;
R
9' be C
1-C
3Alkyl, allyl group, CH
2CH
2OCH
3Or CH
2CH
2Cl;
R
10Be OH, CN or OSO
2CH
3
9.8 in preferred compound, wherein
A is A-1;
X is CH
3, OCH
3, OCH
2CH
3, Cl or OCH
2CF
3;
Y is CH
3, OCH
3, CH
2CH
3, CH
2OCH
3, NHCH
3Or CH(OCH
3)
2
10.9 in preferred compound, wherein Z is CH.
11.9 in preferred compound, wherein Z is N.
12.4 in preferred compound, wherein
R
7Be H, C
2-C
3Cyano group alkyl, allyl group or propargyl;
R
8Be C
1-C
3Alkyl, allyl group, propargyl or cyclopropyl;
13.12 in preferred compound, wherein
A is A-1;
X is CH
3, OCH
3, OCH
2CH
3, Cl or OCH
2CF
3;
Y is CH
3, OCH
3, CH
2CH
3, CH
2OCH
3, NHCH
3Or CH(OCH
3)
2
14.13 in preferred compound, wherein Z is CH.
15.13 in preferred compound, wherein Z is N.
16.5 in preferred compound, wherein
R
7Be H, C
2-C
3Cyano group alkyl, allyl group or propargyl;
R
8Be C
1-C
3Alkyl, allyl group, propargyl or cyclopropyl;
17.16 in preferred compound, wherein
A is A-1;
X is CH
3, OCH
3, OCH
2CH
3, Cl or OCH
2CF
3;
Y is CH
3, OCH
3, CH
2CH
3, CH
2OCH
3, NHCH
3Or CH(OCH
3)
2
18.17 in preferred compound, wherein Z is CH.
19.17 in preferred compound, wherein Z is N.
20.6 in preferred compound, wherein
R
7Be H, C
2-C
3Cyano group alkyl, allyl group or propargyl;
R
8Be C
1-C
3Alkyl, allyl group, propargyl or cyclopropyl;
21.20 in preferred compound, wherein
A is A-1;
X is CH
3, OCH
3, OCH
2CH
3, Cl or OCH
2CF
3;
Y is CH
3, OCH
3, CH
2CH
3, CH
2OCH
3, NHCH
3Or CH(OCH
3)
2
22.21 in preferred compound, wherein Z is CH.
23.21 in preferred compound, wherein Z is N.
24.7 in preferred compound, wherein
R
6Be C
1-C
2Alkylthio, C
1-C
2Alkyl sulphinyl, C
1-C
2Haloalkyl thio, C
1-C
2Haloalkyl sulfinyl, C
1-C
2Halogenated alkyl sulfonyl, SO
2N(OCH
3) CH
3Or SO
2NR
7R
8;
R
7Be H, C
2-C
3Cyano group alkyl, allyl group or propargyl;
R
8Be C
1-C
3Alkyl, allyl group, propargyl or cyclopropyl;
25.24 in preferred compound, wherein
A is A-1;
X is CH
3, OCH
3, OCH
2CH
3, Cl or OCH
2CF
3;
Y is CH
3, OCH
3, CH
2CH
3, CH
2OCH
3, NHCH
3Or CH(OCH
3)
2
26.25 in preferred compound, wherein Z is CH.
27.25 in preferred compound, wherein Z is N.
28.1 in preferred compound, wherein
J is J-1;
A is A-1;
Z is CH;
W is O;
R
2Be C
1-C
4Alkyl sulphinyl or C
1-C
4Alkyl sulphonyl;
R
fBe H, C
1-C
2Alkyl, C
1Haloalkyl, C
1-C
2Alkoxyl group or C
1-C
2Alkylthio.
29.28 in preferred compound, wherein
R
fBe H;
R
2Be C
1-C
4Alkyl sulphonyl;
X is OCH
3;
Y is OCH
3
Particularly preferred compound is as follows for the easiest synthetic and/or best deweeding effect:
N-[(4,6-dimethoxypyridin-2-yl) aminocarboxyl]-3-(1-sulfonyl propyl base)-the 2-Sulphapyridine;
N-[(4,6-dimethoxypyridin-2-yl) aminocarboxyl]-3-(1-propyl group sulfinyl)-the 2-Sulphapyridine;
N-[(4,6-dimethoxypyridin-2-yl) aminocarboxyl]-the 3-(ethylsulfonyl)-the 2-Sulphapyridine;
N2-[(4,6-dimethoxypyridin-2-yl) aminocarboxyl]-N3-ethyl-2,3-pyridine two sulfanilamide (SN);
N-[(4,6-dimethoxypyridin-2-yl) aminocarboxyl]-the 3-(mesyloxy)-the 2-Sulphapyridine;
N2-[(4,6-dimethoxypyridin-2-yl) aminocarboxyl]-N3-methyl-2,3-pyridine two sulfanilamide (SN);
The invention still further relates to the novel cpd of following formula
Wherein Xa is Cl, NH
2, HNC(CH
3)
3With
; They can be used as the herbicidal intermediate product of sulfonylurea.
Particularly preferably be:
3-ethylsulfonyl-2-Sulphapyridine and N3-methyl-2,3-pyridine two sulfanilamide (SN).
Synthetic
The compound of formula I can pass through U.S.4,456, one or more methods described in 469 are synthetic, or shown in reaction formula 1, in the tertiary amine base that waits molal quantity as 1, under the existence of 8-phenodiazine two heterocycles [5.4.0] 11 carbon-7-alkene (DBU), synthesize by the phenyl ester reaction of sulfanilamide (SN) II and suitable carboxylamine III.
Reaction formula 1
Wherein
J, R and A such as front define.
Reaction shown in the reaction formula 1 is best as european patent application 70, and 804(1983 announced January 26) described, under inert atmosphere, in such as diox or acetonitrile solvent, carried out 1-2 hour in 25 ℃.With aqueous hydrochloric acid acidification reaction liquid, can isolate the product of required formula I easily.In addition, useable solvents such as methylene dichloride or ethyl acetate extraction water layer.Solvent seasoning and evaporation are then produced required product.Phenylcarbamate can alkali for example sodium hydride, pyridine or salt of wormwood in the presence of, add the 4-dimethylaminopyridine of catalytic amount, corresponding heterocyclic amine reacted with diphenyl carbonate or phenyl chloroformate and synthesize.In suitable solvent such as tetrahydrofuran (THF), under the temperature between 25-65 ℃, this mixture was stirred 12-36 hour.
The sulfamido of required formula II can synthesize by any of method shown in following reaction formula 2 and 3.
Reaction formula 2 has been described the sulfamido of the SULPHURYL CHLORIDE and the ammonia react production II of formula IV.
Reaction formula 2
Wherein
J such as front define.
The amination of reaction formula 2 can be carried out easily, promptly under the temperature between-30 ° and 25 ℃, undertaken by anhydrous ammonia or the dense ammonium hydroxide that in the solution of SULPHURYL CHLORIDE IV in a kind of suitable solvent (for example Anaesthetie Ether, tetrahydrofuran (THF) or methylene dichloride), adds at least 2 molar equivalents.The sulfamido of required formula II in this case, is removed by-product ammonium chloride by washing with water by filtering separation, or by separating with the appropriate organic solvent extraction, for example with methylene dichloride or ethyl acetate extraction.Solvent seasoning and evaporation are then obtained the product II, and its purity is enough to make it directly to carry out next step usually.
The sulfamido of formula II also can be prepared shown in reaction formula 3, and for example trifluoroacetic acid (TFA), Tripyrophosphoric acid (PPA) or right-toluenesulphonic acids (p-TSA) are handled corresponding N-tert-butyl sulfamido VI promptly to use suitable acid.
Reaction formula 3
JSO
2Uncle NH--Bu (TFA, PPA)/() JSO
2NH
2
VI or
p-TSA????Ⅱ
Wherein
J such as front define.
The reaction of reaction formula 3 can be carried out easily, promptly under about 25 ℃, and the compound of stirring-type IV solution 1-72 hour in excessive trifluoroacetic acid (approximately 0.3M).Remove volatile constituent by vacuum then, crystallization from suitable solvent (for example Anaesthetie Ether, 1-chlorobutane or ethyl acetate) separates required formula II sulfamido again.In addition, the N-tert-butyl sulfamido of formula VI can in for example toluene or xylene solvent, be handled 1-6 hour with the right-toluenesulphonic acids monohydrate of catalytic amount under reflux temperature.Separate required product with method similar to the above again.N-tert-butyl sulfamido go the protection in use Tripyrophosphoric acid, can be referring to J.G.Lombardino, J.Org.Chem., 36:1843(1971); The use of trifluoroacetic acid is referring to J.D.Catt and W.L.Matier, J.Org.Chem., 38:1974(1973).
The sulfamido of formula VI can be shown in reaction formula 4, and the SULPHURYL CHLORIDE by making the formula IV and excessive uncle-butylamine reaction prepare.
Reaction formula 4
Wherein
J such as front define.
The SULPHURYL CHLORIDE of formula IV can be according to U.S.4,456,469 described method preparations.In addition, can use the method in the south african patent application 84/8844, this method has been described by handling with hypochlorite solutions, makes sulfydryl or arylmethyl thio-compounds change into SULPHURYL CHLORIDE.
Shown in reaction formula 5, the SULPHURYL CHLORIDE of formula IV a also can be according to T.Gungor, F.Marsais and G.Queguiner, J.Organomet.Chem., 1981,215, the method for 139-150, the 2-fluoropyridine derivatives is carried out metal with LDA (LDA) replace, then with sulfurous gas and N-chloro-succinimide (NCS) processing and prepare.
Reaction formula 5
Wherein
R
1Define as the front.
The SULPHURYL CHLORIDE of formula IV b can be shown in reaction formula 6 and U.S.4, and 420,325 is described, from the compound of formula VII.
Reaction formula 6
Wherein
J such as front define.
[X] is a kind of suitable halogenating agent, and this is conspicuous for this area professional.
As U.S.4, shown in 456, the 469 described and reaction formula 7, haloperidid compound that the sulfide of formula VIII can be by making the formula IX and suitable mercaptan react in the presence of alkali and prepare.
Reaction formula 7
Wherein
X ' is F, Cl or Br;
R ' is C
1-C
4Alkyl or benzyl.
Shown in reaction formula 8, the sulfide of formula VIII a can be as P.Breant, F.Marsais and G.Queguiner, Synthesis, 1993, the described pyridine compounds with X of 822-824 carries out metal with two normal highly basic such as n-Butyl Lithium or LDA (LDA) and replaces, and then being prepared with suitable disulphide processing.
Reaction formula 8
Wherein
R ' is C
1-C
4Alkyl, C
3-C
5Cycloalkyl or benzyl;
R
1Define as the front.
In a similar manner, the sulfide of formula VIII b can prepare shown in reaction formula 9.
Reaction formula 9
Wherein
R ' is C
1-C
4Alkyl, C
3-C
5Cycloalkyl or benzyl;
R
1Define as the front.
Shown in reaction formula 10, the sulfide of formula VIII c can then handle being prepared as described above by the metal replacement of 2-fluoropyridine derivatives with suitable disulphide.
Reaction formula 10
Wherein
R ' is C
1-C
4Alkyl, C
3-C
5Cycloalkyl or benzyl;
R
1Define as the front.
Shown in reaction formula 11, the sulfone of general formula XI and sulfoxide can prepare with any (as hydrogen peroxide or peracid) in the various oxygenants [O] known in the art corresponding sulfide from formula VIII d.
Reaction formula 11
Wherein
R
1Define as the front.
R ' is C
1-C
4Alkyl or C
3-C
5Cycloalkyl;
N is 1 or 2.
Shown in reaction formula 12, the chloro-pyridine of formula IX a can replace and prepare with cuprous cyanide then by the diazotization of 3-amino-2-chloro-pyridine.One of skill in the art is by the currently known methods in the document, also available other groups such as SO
2Cl and N
3Replace diazonium groups.
Reaction formula 12
Wherein
R
1Define as the front.
The sulfide of general formula VIII f can be prepared shown in reaction formula 13.Utilize multiple alkali for example salt of wormwood or uncle-Ding oxygen potassium, make 3-hydroxyl-2-mercaptopyridine derivative alkylation with alkylogen, obtain the sulfide of formula VIII e, it is handled in the presence of acid acceptor such as triethylamine with suitable SULPHURYL CHLORIDE then, obtain the sulfide of formula VIII f.
Reaction formula 13
Wherein
R ' is C
1-C
4Alkyl or benzyl;
X ' is Cl, Br or I;
R
1And R
8Define as the front.
The ester class of formula VIII g, VIII h and VIII j can be prepared by in two kinds of methods shown in the reaction formula 14 any.First method comprises as front reaction formula 5 described 2-fluoropyridine derivatives metals and replacing, and handles with Vinyl chloroformate or methyl-chloroformate then, then obtains the ester class of formula VIII.7 described thiolate displacements have produced the ester class of formula VIII g as reaction formula.Use suitable alcohol to carry out the ester class that acid catalyzed transesterification obtains formula VIII h as solvent.
Second method comprises utilizes multiple alkali for example salt of wormwood or uncle's fourth oxygen potassium; make 2-sulfydryl nicotinic acid derivates VIII i alkylation with alkylogen; use the conventional reagent of many kinds for example thionyl chloride, phosphorus trichloride or phosphorus pentachloride then, or oxalyl chloride converts it into acyl halide.In the presence of acid acceptor such as triethylamine, handle chloride of acid then, obtain the ester class of formula VIII h with suitable alcohols.Make sulfide VIII h change into sulfanilamide (SN) VIII j as previously described.
X ', R ', R
1, R
9And R
9' define as the front.
The sulfanilamide (SN) of general formula XII a can prepare shown in reaction formula 15.But for the secondary sulfanilamide (SN) for preparing one-level or be not obstructed, the synthesis step of back needs a blocking group.Reaction formula 16 has been represented a representational example, and wherein, the tert-butyl blocking group is used to synthetic sulfanilamide (SN) II a.
Reaction formula 15
Wherein
[D] is Rd, Re, R
7R
8, R
7' R
8Or H
2;
R
1, Rd, Re, R
7, R
8And R
7' define as the front.
Reaction formula 16
Wherein
R
1Define as the front.
The difluoro compound of formula X IV a in the reaction formula 17 can be used aforesaid prepared in reaction.Various R with monovalent
1Nucleophilic reagent (available in this area) is handled, produce a kind of can isolating mixture of products.Provided an example that uses methoxy sodium as nucleophilic reaction reagent.Can isolation of intermediate products X IV b and X IV c, and can make it as previously mentioned further to derive.
Reaction formula 17
Wherein
R
2Define as the front.
Reaction formula 18 has been represented the method for another kind of preparation formula X V d ester class.Can make 2 as previously mentioned, 6-dihalo pyridine carries out the thiolate displacement, changes into sulfanilamide (SN) X V a then.With with P.Breant, F.Marsalis and G.Queguiner, Synthesis, 1983, the described similar methods of 822-824, with two normal highly basic for example just-butyllithium handles, and uses carbon dioxide treatment then, obtains the acids of formula X V b.Then, the available various R of this acid
1Nucleophilic reagent such as alkoxide, thiolate or amine are handled, obtain the acids (as an example) of formula X V c, can utilize 1 of routine then, 3-dicyclohexyl carbodiimide (DCC) coupling condition with sodium methoxide, make their esterifications with suitable alcohols, obtain the ester class of formula X V d.
Reaction formula 18
Wherein
R
9Also can be R
9';
X ' is F or Cl;
R
1', R
9And R
9' define as the front.
With similar methods, the sulfamido of general formula X VI b can prepare shown in reaction formula 19.Handle X V a with highly basic, handle with suitable disulphide then, obtain the sulfide of formula X VI a.Utilize the further processing of aforesaid chemical process then to obtain the sulfamido of formula X VI b.
Wherein
X ' is F or Cl;
R ' and [D] define as the front.
When one of skill in the art selects suitable method for the compound of preparation formula I, must consider substituent R
1To R
11, Rd to Rg character, and the chemical compatibility of the reaction conditions of they and reaction formula 1 to 19.
In the top reaction formula 1, the heterocyclic amine of formula A-NHR can be by one of skill in the art by known method in the document or its simply improved method preparation.For example, EP-A84,224(1983 announced July 27) and people such as W.Braker, J.Chem.Soc., 69:3072(1947) the preparation aminopyridine has been described and the method for the triazine that replaces by acetal group (for example dialkoxy methyl or 1,3-dioxolane-2-base etc.).In addition, for example, south african patent application 82/5045 and 82/5671 has been described the preparation aminopyrimidine and by haloalkyl or haloalkyl sulfenyl (OCH for example
2CH
2F, OCH
2CF
3, SCF
2H or OCF
2H etc.) method of the triazine of Qu Daiing.South african patent application 83/7434(1983 announced October 5) method of the triazine of synthetic cyclopropyl pyrimidine and replacement has been described, substituting group has for example alkyl, haloalkyl, alkoxyl group, halogenated alkoxy, alkylamino, dialkyl amido or alkoxyalkyl.
As EP-A15,683 is described, can prepare 5,6-dihydrofuran [2.3-d] pyrimidine-2-amine, ring penta [d] pyrimidine-2-amine (A is A-2) and 6,7-dihydro-5H-pyrans [2.3-d] pyrimidine-2-amine (A is A-3).EP-A46,677 have described furans [2.3-d] pyrimidine-2-amine (A is A-4).
EP-A-73,562 have described wherein, and A is the compound of the formula A-NHR of A-5.EP-A-94,260 have described wherein, and A is the compound of A-6.
In addition, following publication has been summarized the general method of preparation aminopyrimidine and triazine:
" The Chemistry of Heterocyclic Compounds ", Interscience Publishers, Inc., the Public Series of New York and London.
" Pyrimidines ", the D.J.Brown work is rolled up with the 16th in a series of;
" s-Triazines and Derivatives ", E.M.Smolin and L.Rappoport work are rolled up with the 13rd in a series of;
F.C.Schaefer, United States Patent (USP) 3,154,547 and K.R.Huffman and F.C.Schaefer, J.Org.Chem., 28,1812(1963), the synthetic of triazine described wherein.
It seems from above, prepare conspicuous for those skilled in the art.The salt that is applicable to the compound of agriculture formula I also is useful weedkiller, and can be prepared by several different methods known in the art.For example, the compound of formula I is contacted with the basic metal with negatively charged ion (as oxyhydroxide, alkoxide, carbonate or oxyhydroxide) that enough alkalescence is arranged or the solution of alkaline earth salt, can prepare metallic salt.Can prepare the quaternary ammonium compound salt with similar techniques.
The salt of the compound of formula I also can be prepared by exchanging a positively charged ion.The aqueous solution (for example basic metal or quarternary ammonium salt) of salt of the compound of formula I is directly contacted with containing the cationic solution that remains to be exchanged, can carry out cationic exchange.This method is the most effective when the required salt that contains exchange cation is water insoluble, and salt can be come out by filtering separation.
Also the aqueous solution (for example basic metal or level Four amine salt) of the salt of the compound of formula I can be exchanged by the post with the Zeo-karb filling, contain in this resin with original salt in the positively charged ion of cationic exchange.The required product of wash-out from post.When required salt when being water-soluble, this method is especially suitable, for example potassium, sodium or calcium salt.
Can be used for acid salt class of the present invention, compound that can be by making the formula I and suitable acid-respons (for example tosic acid, trichoroacetic acid(TCA) etc.) obtain.
Following specific examples further specifies the preparation of compound of the present invention.Temperature is meant degree centigrade; The used abbreviation of this mr (NMR) is: s=is unimodal, and d=is bimodal, t=three peaks, the m=multiplet, be meant the ppm downfield of inner tetramethylsilane to peak position.To give infrared (IR) peak position be reciprocal centimetre (cm
-1).
Example 1
2-fluoro-3-(rosickyite base) preparation of pyridine
Under nitrogen, to the 59ml(0.113 mole that is stirring) LDA (in hexane) of 1.9M is cooled in 150ml the solution in-70 ° the anhydrous tetrahydro furan, drip the solution of 10.0g 2-fluorine pyridine (0.103 mole) in the 30ml anhydrous tetrahydro furan, so that temperature maintenance is below-65 °.This solution was stirred 4 hours down at-70 ℃, and drip 17g just-solution of propyl disulfide thing (0.113 mole) in the 45ml anhydrous tetrahydro furan, make temperature maintenance below-65 ° simultaneously., this solution is poured in the water, and used extracted with diethyl ether after 1 hour at-70 ° of following restir.Dried over mgso is used in the organic phase salt water washing that merges, and obtains 14.5g(82% after the evaporation) a kind of red oil:
NMR(CDCl
3, 200MHz), 1.0(3H, m), 1.7(2H, m), 2.9(2H, m), 7.1(1H, m), 7.7(1H, m), 8.0(1H, m); The IR(absolute oil) 1585,1560,1410,1245cm
-1.
Example 2
2-(phenyl methylthio group)-and 3-(rosickyite base) preparation of pyridine
Under nitrogen, to the 0.62g(0.013 mole that is stirring) 50% sodium hydride is (in mineral oil, cross with hexane wash) be cooled in 20ml the suspension in-5 ° the anhydrous dimethyl formamide, drip the 1.6g(0.013 mole) benzyl mercaptan, so that temperature maintenance is below 5 ℃.This suspension was at room temperature stirred 1 hour, is cooled to 0 ℃, and drip the 2.0g(0.012 mole) solution of the product of example 1, make temperature maintenance simultaneously between 0 ° and 5 °.Be heated to after the room temperature, pour into this solution in the water and use extracted with diethyl ether.The organic layer water and the salt water washing that merge with dried over mgso and be evaporated to oily, obtain 0.9g(27% by the flash chromatography purifying) oily matter:
NMR(CDCl
3, 200MHz), 1.02(3H, t, J=7Hz), 1.6(2H, m), and 2.9(2H, t, J=7Hz), 4.45(2H, s), 6.9-7.6(7H, m), 8.3(1H, m); The IR(absolute oil) 1560,1370cm
-1.)
Example 3
N(1,1-dimethyl ethyl)-2-(propyl group sulfinyl)-preparation of 2-Sulphapyridine
Being cooled to 0 ° 0.5g(0.0018 mole to what vigorous stirring) product of example 2 is in the mixture of 9ml methylene dichloride and 4ml water, add the 0.7ml(0.008 mole) concentrated hydrochloric acid, then drip the 8.9ml(0.006 mole) 5% chlorine bleach liquor, make temperature maintenance between 0 ° and 5 °.Make the mixture restir after 30 minutes at 0 °, pour into reaction solution in the water and use dichloromethane extraction.The organic layer salt water washing that merges is with dried over mgso and filtration.Filtrate stirred under nitrogen and be cooled to-70 °, drip the 0.53g(0.0072 mole then) uncle-butylamine, with this mixture heating up to room temperature.Pour into reactant in the water and use dichloromethane extraction.Merge organic layer and use the salt water washing, use dried over mgso, flash to a kind of mixture,, obtain 0.4g(69% by the flash chromatography purifying) white solid: fusing point 138-140 °,
NMR(CDCl
3, 200MHz) 1.09(3H, m), 1.7(1H, m), 2.0(1H, m), 2.8(1H, m), 3.3(1H, m), 5.2(NH), 7.7(1H, m), 8.6(1H, m), 8.8(1H, m); The IR(whiteruss) 3400,1375,1325,1160,1065,1015cm
-1.)
Example 4
3-(sulfonyl propyl base)-preparation of 2-Sulphapyridine
Under nitrogen, to the 8.8g(0.029 mole that is stirring) product of example 3 is cooled at 400ml in-5 ° the solution of methylene dichloride, adds the 6.6g(0.038 mole) 3-chlorine peroxybenzoic acid, and at room temperature stirred 20 hours.Pour into this reaction mixture in the water and use dichloromethane extraction.Merge organic layer and, use dried over mgso, flash to a kind of solid mixture, it is used hexane wash, obtain a kind of white solid with saturated sodium bisulfite and salt water washing.Be dissolved in this solid in the 150ml trifluoroacetic acid and stirred 72 hours.Evaporate this solution, and, obtain 5.3g(46% with the ether development) white solid: fusing point 153-157 °;
NMR(CDCl
3, 200MHz) 1.06(3H, t, J=7Hz), 1.8(2H, m), 3.7(2H, m) 5.8(NH
2), 7.8(1H, m), 8.6(1H, m), 8.95(1H, m); The IR(whiteruss) 3390,3180,1360,1310,1175,1150cm
-1.
Example 5
N-[(4,6-SDM-2-yl) aminocarboxyl]-3-(sulfonyl propyl base)-preparation of 2-Sulphapyridine
To the 0.4g(0.0015 mole that is stirring) product and the 0.63g (0.0023 mole) (4 of example 4,6-dimethoxypyridin-2-yl) in the suspension of phenyl carbamate in the 4ml acetonitrile, add the 0.35g(0.0023 mole) 1,8-phenodiazine two heterocycles [5.4.0] 11 carbon-7-alkene, and stirred 30 minutes.This solution of dilute with water, and use the 1N hcl acidifying.Collect the throw out and water and the ether washing that are produced, obtain 0.45g(67%) white solid: fusing point 168-170 °,
NMR(CDCl
3, 200MHz), 1.07(3H, t, J=7Hz), 1.85(2H, m), 3.7(2H, m), 3.97(6H, s), 5.8(1H, s), and 7.26(NH), 7.8(1H, m), 8.6(1H, m), 8.9(1H, m), 12.9(NH); The IR(whiteruss) 3320,1740,1610,1580,1375,1195,1170cm
-1.
Example 6
The preparation of 3-ethylmercapto group-2-fluorine pyridine
The method of use-case 1 changes into 46.5g(72% with 40.0g 2-fluorine pyridine (0.412 mole)) title compound, be an oily matter:
NMR(CDCl
3, 200MHz) 1.3(3H, t, J=7Hz), and 2.95(2H, q, J=7Hz), 7.1(1H, m), 7.7(1H, m), 8.0(1H, m); The IR(absolute oil) 1585,1565,1410,1230cm
-1.
Example 7
3-ethylmercapto group-2-(phenyl methylthio group)-preparation of pyridine
The method of use-case 2 is with the 25.0g(0.160 mole) product of example 6 changes into 44.8g(100%) title compound, be a kind of yellow liquid:
NMR(CDCl
3, 200MHz) 1.28(3H, t, J=7Hz), and 2.9(2H, q, J=7Hz), 4.45(2H, s), 7.0-7.6(7H, m), 8.35(1H, m); The IR(absolute oil) 1610,1405cm
-1.
Example 8
N-(1,1-dimethyl ethyl)-preparation of 3-ethyl sulfinyl-2-Sulphapyridine
The method of use-case 3 is with the 35.0g(0.134 mole) product of example 7 changes into 21.2g(56%) title compound: fusing point: 129-131 °;
NMR(CDCl
3, 200MHz) 1.23(9H, s), 1.28(3H, t, J=7Hz), 2.9(1H, m), 3.3(1H, m), and 5.2(NH), 7.7(1H, m), 8.55(1H, m), 8.75(1H, m); The lR(whiteruss) 3100,1320,1155cm
-1.
Example 9
N-(1,1-dimethyl ethyl)-preparation of 3-ethylsulfonyl-2-Sulphapyridine
The first half method of use-case 4 (be 3-chlorine peroxybenzoic acid reaction) is with the 9.0g(0.033 mole) product of example 9 changes into 10.1g(100%) title compound: fusing point: 58-63 °;
NMR(CDCl
3, 200MHz) 1.2(3H, t, J=7Hz), 1.2(9H, s), and 3.7(2H, q, J=7Hz), and 6.1(NH), 7.7(1H, m), 8.55(1H, m), 8.95(1H, m); The lR(whiteruss) 3300,1560,1350,1300,1170,1140cm
-1.
Example 10
The preparation of 3-ethylsulfonyl-2-Sulphapyridine
The latter half method of use-case 4 (be trifluoroacetic acid reaction) is with the 9.0g(0.029 mole) product of example 9 changes into 4.2g(58%) title compound: fusing point: 211-212.5 °;
NMR(DMSO-d
6, 200MHz) 1.15(3H, t, J=7Hz), 3.4(NH
2), 3.7(2H, q, J=7Hz), 7.9(1H, m), 8.5(1H, m), 8.95(1H, m); The IR(whiteruss) 3370,3190,1350,1310,1180cm
-1.
Example 11
N-[(4,6-dimethoxypyridin-2-yl)-aminocarboxyl]-preparation of 3-ethylsulfonyl-2-Sulphapyridine
The method of use-case 5 is with the 0.60g(0.0024 mole) product of example 10 changes into 0.70g(70%) title compound: fusing point: 160-162 °;
NMR(CDCl
3, 200MHz) 1.35(3H, t, J=7Hz), and 3.7(2H, q, J=7Hz), 3.97(6H, s), 5.8(1H, s), and 7.3(NH), 7.75(1H, m), 8.6(1H, m), 8.9(1H, m), 12.95(NH); The IR(whiteruss) 3260,1740,1610,1360,1195,1175cm
-1.
Example 12
2,6-two fluoro-3-pyridine carboxylic acids, the preparation of methyl ester
Under nitrogen, to the 91ml(0.182 mole that is stirring) LDA (in hexane) of 2.0M is cooled to the solution in-70 ° the anhydrous tetrahydro furan at 200ml, drip 20.0g 2, the solution of 6-difluoro pyridine (0.174 mole) in the 75ml anhydrous tetrahydro furan is so that temperature maintenance is below-60 °.This solution was stirred 3 hours down at-70 ℃, then under nitrogen, adding to the 21.7g(0.230 mole by sleeve pipe) methyl-chloroformate is cooled at 100ml in-70 ° the solution of anhydrous tetrahydro furan, and at-70 ° of following restir after 1 hour, pour into this mixture in the water and use extracted with diethyl ether.The organic layer salt water washing that merges is used dried over mgso, and is evaporated to semisolid, by the flash chromatography purifying, obtains 13.0g(43%) orange oily matter:
NMR(CDCl
3, 200MHz) 3.95(3H, s), 6.9(1H, m), 8.5(1H, m); The IR(absolute oil) 1745,1730,1610,1415,1290cm
-1.
Example 13
The preparation of 2-fluoro-6-methoxyl group-3-pyridine carboxylic acid methyl ester
With 40 minutes time, to the 15.0g(0.0867 mole that is stirring) example 12 products are cooled at 240ml in-78 ° the solution of anhydrous tetrahydro furan, drip the 22.7ml(0.0993 mole) solution of 25% methoxy sodium in methanol solution.After being heated to-20 ℃, this mixture is poured in the frozen water, with the 1N hcl acidifying and use extracted with diethyl ether.The organic layer salt water washing that merges is used dried over mgso, and is evaporated to semisolid, by the flash chromatography purifying, obtains 3.2g(17%) faint yellow solid: fusing point 81-82 °;
NMR(CDCl
3, 200MHz) 3.9(3H, s), 3.98(3H, s), 6.67(1H, d, J=9Hz), 8.25(1H, m); The IR(whiteruss) 1715,1615,1290cm
-1.
Example 14
6-methoxyl group-2-(phenyl methylthio group)-preparation of 3-pyridine carboxylic acid methyl ester
Under nitrogen, to the 0.8g(0.0161 mole that is stirring) 50% sodium hydride is (in mineral oil, cross with hexane wash) be cooled at 20ml in the mixture in-5 ° the anhydrous dimethyl formamide, drip the 1.9ml(0.0161 mole) benzyl mercaptan.This suspension was at room temperature stirred 1 hour, is cooled to 0 °, and drip the 3.2g(0.0147 mole) solution of product in the 20ml anhydrous dimethyl formamide of example 13.After being heated to room temperature, pouring into this solution in the water and use extracted with diethyl ether.Dried over mgso use in the organic layer water and the salt water washing that merge, passes through the flash chromatography purifying after being evaporated to oily, obtains 3.0g(64%) yellow solid: fusing point 67-71 °;
NMR(CDCl
3, 200MHz) 3.88(3H, s), 3.96(3H, s), 4.46(2H, s), 6.44(1H, d, J=9Hz), 7.2-7.5(5H, m), and 8.1(1H, d, J=9Hz); The IR(whiteruss) 1700,1580,1305,1255cm
-1.
Example 15
2-[1,1-dimethyl ethyl) amino-sulfonyl]-preparation of 6-methoxyl group-3-pyridine carboxylic acid methyl ester
To the 3.7g(0.0129 mole that vigorous stirring) product of example 14 is being cooled in 0 ° the 79ml methylene dichloride and the mixture in the 41ml water, add the 6.3ml(0.0759 mole) concentrated hydrochloric acid, then drip the 79ml(0.053 mole) 5% chlorine bleach liquor, so that temperature remains on below 5 °.Under 0 ° with this mixture restir after 30 minutes, pour into reactant in the water and use dichloromethane extraction.The organic layer salt water washing that merges is with dried over mgso and filtration.Under nitrogen, stir filtrate and be cooled to-70 °, drip the 4.7g(0.0645 mole then) uncle-butylamine.This reaction mixture is heated to-20 °, pours in the water, use the 1N hcl acidifying, and use dichloromethane extraction.Dried over mgso is used in the organic layer salt water washing that merges, and is evaporated to semisolid, by the flash chromatography purifying, obtains 3.0g(77%) yellow solid: fusing point 128-130 °;
NMR(CDCl
3, 200MHz) 1.27(9H, s), 3.94(3H, s), 4.05(3H, s) 5.75(NH), 6.9(1H, d, J=9Hz), and 7.95(1H, d, J=9HZ); The IR(whiteruss) 3260,1740,1605,1325,1125cm
-1.
Example 16
The 2-(amino-sulfonyl)-preparation of 6-methoxyl group-3-pyridine carboxylic acid methyl ester
At room temperature, with the 2.9g(0.0096 mole) product of example 15 stirred 20 hours at the 50ml trifluoroacetic acid.Evaporate this solution and obtain 2.4g(100%) white solid: fusing point: 142.5-144.5 °;
NMR(CDCl, 200MHz) 3.97(3H, s), 4.1(3H, s), 5.6(NH
2), 6.9(1H, d, J=9Hz), and 8.1(1H, d, J=9Hz); The IR(whiteruss) 3305,3205,1715,1590,1355,1320,1175cm
-1.
Example 17
2-[[(4,6-SDM-2-yl) aminocarboxyl] amino-sulfonyl]-preparation of 6-methoxyl group-3-pyridine carboxylic acid methyl ester
To the 0.4g(0.0016 mole that is stirring) product and the 0.54g(0.002 mole of example 16) (4,6-dimethoxypyridin-2-yl) in the suspension of phenyl carbamate in the 4ml acetonitrile, drip the 0.30g(0.002 mole) 1.8-phenodiazine two heterocycles [5.4.0] 11 carbon-7-alkene and stirring 30 minutes.This solution of dilute with water is also used the 1N hcl acidifying.Collect the throw out and water and the ether washing that are produced, obtain 0.57g(84%) white solid: fusing point 194-196 °;
NMR(CDCl
3, 200MHz), 3.83(3H, s), 3.95(9H, s), 5.8(1H, s), and 6.95(1H, d, J=9Hz), and 7.4(NH), 8.1(1H, d, J=9Hz), 12.8(NH); The IR(whiteruss) 3140,1740,1720,1640,1360,1195,1140cm
-1.
Example 18
N-(1,1-dimethyl ethyl)-preparation of 2-fluoro-3-Sulphapyridine
Under nitrogen, to the 396ml(0.740 mole that is stirring) LDA (in hexane) of 1.9M is cooled at 1.5L in the solution in-70 ° the anhydrous tetrahydro furan, dropping 65g(0.670 mole) the solution of 2-difluoro pyridine in the 150ml anhydrous tetrahydro furan is so that temperature remains on below-65 °.With this suspension-70 ℃ of following restir 3.5 hours, and add the 86g(1.34 mole) sulfurous gas, maintain the temperature at simultaneously below-65 °.After 15 minutes, this reaction solution is heated to 0 ° at-70 ° of following restir.Dilute with ether half back that is evaporated to original volume.Under nitrogen, collect white depositions, wash after drying with ether.Be dissolved in this solid in the 800ml acetate and be cooled to 10-20 °.In the solution that this is stirring, add the 99.4g(0.740 mole in batches) N-chloro-succinimide, maintain the temperature at simultaneously below 20 °.After the restir 30 minutes, evaporate this suspension, dilute with water is also used dichloromethane extraction.The organic phase that merges with saturated sodium bicarbonate aqueous solution washing, till no longer including gas and sending, use the salt water washing, with also filtration of dried over mgso.Filtrate is cooled to-70 ° under nitrogen, and in the solution that this is stirring, drips the 199g(2.7 mole) uncle-butylamine.This suspension is poured in the frozen water, used the concentrated hydrochloric acid acidifying, and use dichloromethane extraction.The organic layer salt water washing that merges, use dried over mgso, be evaporated to behind the oily, obtain 29.1g(19% by the flash chromatography purifying) brown solid, with its further with cold just-the Butyryl Chloride washing, obtain 22.4g(14.5%) white solid: fusing point 95-97 °;
NMR(CDCl
3,200MHz)1.25(9H,s),4.9(NH),7.35(1H,m),8.3-8.5(2H,m).
Example 19
N-(1,1-dimethyl ethyl)-preparation of 2-fluoro-N-methyl-3-Sulphapyridine
Under nitrogen, to the 3.4g(0.071 mole that is stirring) 50% sodium hydride is (in mineral oil, cross with hexane wash) in 120ml is cooled to suspension in 0 ° the anhydrous dimethyl formamide, drip the 15.0g(0.065 mole) solution of product in the 120ml anhydrous dimethyl formamide of example 18.After at room temperature stirring 1 hour, this mixture is cooled to 0 °, and drips the 12.2g(0.086 mole) methyl-iodide.After being heated to room temperature, pouring into reactant in the frozen water and use extracted with diethyl ether.The organic layer salt water washing that merges with dried over mgso and evaporation, obtains 15.9g(99%) oily matter:
NMR(CDCl
3, 200MHz), 1.32(9H, s), 3.1(3H, s), 7.3(1H, m), 8.3-8.4(2H, m); The IR(absolute oil) 1590,1570,1335,1155cm
-1.
Example 20
N-(1,1-dimethyl ethyl)-N-methyl-2-(phenyl methylthio group)-preparation of 3-Sulphapyridine
Use the same procedure with example 14, with the 15.9g(0.065 mole) product of example 19 changes into 19.5g(86%) yellow solid: fusing point: 92-94 °;
NMR(CDCl
3), 200MHz) 1.26(9H, s), 3.1(3H, s), 4.5(2H, s), 7.0-7.5(6H, m), 8.2(1H, m); The IR(whiteruss) 1570,1385,1315,1150,1120cm
-1.
Example 21
N2, two (1,1-diformazan the ethyl)-N3-methyl-2 of N3-, the preparation of 3-pyridine two sulfanilamide (SN)
Use the method identical, with the 19.5g(0.056 mole with example 15) product of example 20 changes into brown solid, with its with just-Butyryl Chloride washs, and obtains 13.1g(66%) white solid: fusing point: 155-156.5 °;
NMR(CDCl
3, 200MHz) 1.23(9H, s), 1.33(9H, s), 3.1(3H, s), 6.0(NH), 1H, m), 8.5(1H, m), 8.8(1H, m); The lR(whiteruss) 3320,1340,1325,1160,1120cm
-1.
Example 22
N3-methyl-2, the preparation of 3-pyridine two sulfanilamide (SN)
With the 13.1g(0.036 mole that is stirring) product of example 21 solution in the 150ml trifluoroacetic acid refluxed 5 hours.After being cooled to room temperature, this solution evaporation to solid, with the ether washing, is obtained 9.6g(100%) white solid: fusing point: 220-223 °;
NMR(DMSO-d
6, 200MHz), 2.5(3H, d), and 6.9(NH), 7.65(NH
2), 7.85(1H, m), 8.45(1H, m), 8.9(1H, m); The IR(whiteruss) 3380,3320,3180,1355,1170cm
-1.
Example 23
N2-[(4,6-dimethoxypyridin-2-yl) aminocarboxyl]-N3-methyl-2, the preparation of 3-pyridine two sulfanilamide (SN)
To the 4.15g(0.0165 mole that is stirring) product and the 5.0g(0.018 mole of example 22) (4,6-dimethoxypyridin-2-yl) in the suspension of phenyl carbamate in the 50ml acetonitrile, drip the 2.8g(0.018 mole) 1.8-phenodiazine two heterocycles [5.4.0] 11 carbon-4-alkene and stirring 30 minutes.This solution of dilute with water, and use the 1N hcl acidifying.Collect the throw out and water and the ether washing that are produced, obtain 6.4g(82%) white solid: fusing point 147-148.5 °;
NMR(CDCl
3, 200MHz) 2.7(3H, d, J=7Hz), 3.97(6H, s), 5.8(1H, s), 6.15(1H, m), and 7.3(NH), 7.7(1H, m), 8.55(1H, m), 8.8(1H, m), 13.1(NH); The IR(whiteruss) 3310,1740,1610,1340,1190,1165cm
-1.
By the method with example 1 to 23 and reaction formula 1 to 19, one of skill in the art can prepare all cpds of table I to the X.
Used general formula in the table
The table I
General formula 1
R
1R
2R X Y Z m.p.(℃)
H SOCH
3H OCH
3OCH
3CH 170-174
H SOCH
3H OCH
3CH
3CH 138-140
H SOCH
3H Cl OCH
3CH 124-126
H SOCH
3H CH
3CH
3CH 126-127.5
H SOCH
3H OCH
3OCH
3N
H SOCH
3H OCH
3CH
3N 165-167
H SOCH
3H OCH
2CH
3NHCH
3N
H SOCH
3CH
3OCH
3CH
3N 133-137
4-CH
3SOCH
3H OCH
3OCH
3CH
4-OCH
3SOCH
3H OCH
3OCH
3CH
6-CH
3SOCH
3H OCH
3OCH
3CH
6-OCH
3SOCH
3H OCH
3OCH
3CH
6-F SOCH
3H OCH
3OCH
3CH
6-Cl SOCH
3H OCH
3OCH
3CH
H SO
2CH
3H OCH
3OCH
3CH 170-172
H SO
2CH
3H OCH
3CH
3CH 158-160
H SO
2CH
3H Cl OCH
3CH 158-160
H SO
2CH
3H CH
3CH
3CH 162-164
H SO
2CH
3H OCH
3OCH
3N 180-184
H SO
2CH
3H OCH
3CH
3N 154-156.5
H SO
2CH
3H OCH
2CH
3NHCH
3N
H SO
2CH
3CH
3OCH
3CH
3N
4-CH
3SO
2CH
3H OCH
3OCH
3CH
4-OCH
3SO
2CH
3H OCH
3OCH
3CH
6-CH
3SO
2CH
3H OCH
3OCH
3CH
6-OCH
3SO
2CH
3H OCH
3OCH
3CH
6-F SO
2CH
3H OCH
3OCH
3CH
6-Cl SO
2CH
3H OCH
3OCH
3CH
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
H SOCH
2CH
3H OCH
3OCH
3CH 132-136
H SOCH
2CH
3H OCH
3CH
3CH 141-144
H SOCH
2CH
3H Cl OCH
3CH 105-107.5
H SOCH
2CH
3H CH
3CH
3CH 153-156.5
H SOCH
2CH
3H OCH
3OCH
3N 154-158
H SOCH
2CH
3H OCH
3CH
3N 172-174
H SOCH
2CH
3H OCH
2CH
3NHCH
3N
H SOCH
2CH
3CH
3OCH
3CH
3N
4-CH
3SOCH
2CH
3H OCH
3OCH
3CH
4-OCH
3SOCH
2CH
3H OCH
3OCH
3CH
6-CH
3SOCH
2CH
3H OCH
3OCH
3CH
6-OCH
3SOCH
2CH
3H OCH
3OCH
3CH
6-F SOCH
2CH
3H OCH
3OCH
3CH
6-Cl SOCH
2CH
3H OCH
3OCH
3CH
H SO
2CH
2CH
3H OCH
3OCH
3CH 160-162
H SO
2CH
2CH
3H OCH
3CH
3CH 160-162
H SO
2CH
2CH
3H Cl OCH
3CH 163-164.5
H SO
2CH
2CH
3H CH
3CH
3CH 167-169
H SO
2CH
2CH
3H OCH
3OCH
3N 155-158
H SO
2CH
2CH
3H OCH
3CH
3N 165.5-168
H SO
2CH
2CH
3H OCH
2CH
3NHCH
3N
H SO
2CH
2CH
3CH
3OCH
3CH
3N 137-138
4-CH
3SO
2CH
2CH
3H OCH
3OCH
3CH
4-OCH
3SO
2CH
2CH
3H OCH
3OCH
3CH
6-CH
3SO
2CH
2CH
3H OCH
3OCH
3CH 178-180
6-CH
3SO
2CH
2CH
3H OCH
3CH
3CH 169.5-172
6-CH
3SO
2CH
2CH
3H CH
3CH
3CH 172-173.5
6-CH
3SO
2CH
2CH
3CH
3OCH
3CH
3N 133-135
6-OCH
3SO
2CH
2CH
3H OCH
3OCH
3CH 210-213
6-F SO
2CH
2CH
3H OCH
3OCH
3CH 157-160
6-F SO
2CH
2CH
3H CH
3CH
3CH 176-177
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
6-Cl SO
2CH
2CH
3H OCH
3OCH
3CH 187-189
6-Cl SO
2CH
2CH
3H Cl OCH
3CH 171-174
6-Cl SO
2CH
2CH
3H CH
3CH
3CH 181-182
6-SCH
3SO
2CH
2CH
3H OCH
3OCH
3CH
6-SCH
3SO
2CH
2CH
3H Cl OCH
3CH
5-CH
3SO
2CH
2CH
3H OCH
3OCH
3CH 159-160
5-CH
3SO
2CH
2CH
3H Cl OCH
3CH 176-177
5-CH
3SO
2CH
2CH
3H OCH
3OCH
3N 155-156
5-CH
3SO
2CH
2CH
3H OCH
3CH
3N 159-161
H SOCH
2CH
2CH
3H OCH
3OCH
3CH 111-115
H SOCH
2CH
2CH
3H OCH
3CH
3CH 141-145
H SOCH
2CH
2CH
3H Cl OCH
3CH 111-113
H SOCH
2CH
2CH
3H CH
3CH
3CH 173-175
H SOCH
2CH
2CH
3H OCH
3OCH
3N 186-189
H SOCH
2CH
2CH
3H OCH
3CH
3N 164-166
H SOCH
2CH
2CH
3H OCH
2CH
3NHCH
3N 121-123
H SOCH
2CH
2CH
3CH
3OCH
3CH
3N
4-CH
3SOCH
2CH
2CH
3H OCH
3OCH
3CH
4-OCH
3SOCH
2CH
2CH
3H OCH
3OCH
3CH
6-CH
3SOCH
2CH
2CH
3H OCH
3OCH
3CH
6-OCH
3SOCH
2CH
2CH
3H OCH
3OCH
3CH
6-F SOCH
2CH
2CH
3H OCH
3OCH
3CH
6-Cl SOCH
2CH
2CH
3H OCH
3OCH
3CH
H SO
2CH
2CH
2CH
3H OCH
3OCH
3CH 168-170
H SO
2CH
2CH
2CH
3H OCH
3CH
3CH 157-159
H SO
2CH
2CH
2CH
3H Cl OCH
3CH 165-167
H SO
2CH
2CH
2CH
3H CH
3CH
3CH 158-160
H SO
2CH
2CH
2CH
3H OCH
3OCH
3N 164-166
H SO
2CH
2CH
2CH
3H OCH
3CH
3N 165-168
H SO
2CH
2CH
2CH
3H OCH
2CH
3NHCH
3N 148-152
H SO
2CH
2CH
2CH
3CH
3OCH
3CH
3N
4-CH
3SO
2CH
2CH
2CH
3H OCH
3OCH
3CH
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
4-OCH
3SO
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-CH
3SO
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-OCH
3SO
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-F SO
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-Cl SO
2CH
2CH
2CH
3H OCH
3OCH
3CH
H SOCH(CH
3)
2H OCH
3OCH
3CH 144-147
H SOCH(CH
3)
2H OCH
3CH
3CH 143-145.5
H SOCH(CH
3)
2H Cl OCH
3CH 133-135
H SOCH(CH
3)
2H CH
3CH
3CH 150-153
H SOCH(CH
3)
2H OCH
3OCH
3N 155-159
H SOCH(CH
3)
2H OCH
3CH
3N 150-153
H SOCH(CH
3)
2H OCH
2CH
3NHCH
3N
H SOCH(CH
3)
2CH
3OCH
3CH
3N
4-CH
3SOCH(CH
3)
2H OCH
3OCH
3CH
4-OCH
3SOCH(CH
3)
2H OCH
3OCH
3CH
6-CH
3SOCH(CH
3)
2H OCH
3OCH
3CH
6-OCH
3SOCH(CH
3)
2H OCH
3OCH
3CH
6-F SOCH(CH
3)
2H OCH
3OCH
3CH
6-Cl SOCH(CH
3)
2H OCH
3OCH
3CH
H SO
2CH(CH
3)
2H OCH
3OCH
3CH 140-146
H SO
2CH(CH
3)
2H OCH
3CH
3CH 159-160.5
H SO
2CH(CH
3)
2H Cl OCH
3CH 164-165.5
H SO
2CH(CH
3)
2H CH
3CH
3CH 161-163
H SO
2CH(CH
3)
2H OCH
3OCH
3N 164-166
H SO
2CH(CH
3)
2H OCH
3CH
3N 165-167
H SO
2CH(CH
3)
2H OCH
2CH
3NHCH
3N
H SO
2CH(CH
3)
2CH
3OCH
3CH
3N 145-149
4-CH
3SO
2CH(CH
3)
2H OCH
3OCH
3CH
4-OCH
3SO
2CH(CH
3)
2H OCH
3OCH
3CH
6-CH
3SO
2CH(CH
3)
2H OCH
3OCH
3CH
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
6-OCH
3SO
2CH(CH
3)
2H OCH
3OCH
3CH
6-F SO
2CH(CH
3)
2H OCH
3OCH
3CH
6-Cl SO
2CH(CH
3)
2H OCH
3OCH
3CH
H SOCH
2CH
2CH
2CH
3H OCH
3OCH
3CH
H SOCH
2CH
2CH
2CH
3H OCH
3CH
3CH
H SOCH
2CH
2CH
2CH
3H Cl OCH
3CH
H SOCH
2CH
2CH
2CH
3H CH
3CH
3CH
H SOCH
2CH
2CH
2CH
3H OCH
3OCH
3N
H SOCH
2CH
2CH
2CH
3H OCH
3CH
3N
H SOCH
2CH
2CH
2CH
3H OCH
2CH
3NHCH
3N
H SOCH
2CH
2CH
2CH
3CH
3OCH
3CH
3N
4-CH
3SOCH
2CH
2CH
2CH
3H OCH
3OCH
3CH
4-OCH
3SOCH
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-CH
3SOCH
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-OCH
3SOCH
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-F SOCH
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-Cl SOCH
2CH
2CH
2CH
3H OCH
3OCH
3CH
H SO
2CH
2CH
2CH
2CH
3H OCH
3OCH
3CH 155-157
H SO
2CH
2CH
2CH
2CH
3H OCH
3CH
3CH 142-144
H SO
2CH
2CH
2CH
2CH
3H Cl OCH
3CH 151-153
H SO
2CH
2CH
2CH
2CH
3H CH
3CH
3CH 142-143
H SO
2CH
2CH
2CH
2CH
3H OCH
3OCH
3N 153.5-155
H SO
2CH
2CH
2CH
2CH
3H OCH
3CH
3N 142.5-145.5
H SO
2CH
2CH
2CH
2CH
3H OCH
2CH
3NHCH
3N
H SO
2CH
2CH
2CH
2CH
3CH
3OCH
3CH
3N
H SO
2CH
2CH
2CH
2CH
3CH
3OCH
3OCH
3N 133-136
4-CH
3SO
2CH
2CH
2CH
2CH
3H OCH
3OCH
3CH
4-OCH
3SO
2CH
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-CH
3SO
2CH
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-OCH
3SO
2CH
2CH
2CH
2CH
3H OCH
3OCH
3CH
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
H SO-cyclopropyl H OCH
3OCH
3CH
H SO-cyclopropyl H OCH
3CH
3CH
H SO-cyclopropyl H Cl OCH
3CH
H SO-cyclopropyl H CH
3CH
3CH
H SO-cyclopropyl H OCH
3OCH
3N
H SO-cyclopropyl H OCH
3CH
3N
H SO-cyclopropyl H OCH
2CH
3NHCH
3N
H SO-cyclopropyl CH
3OCH
3CH
3N
4-CH
3SO-cyclopropyl H OCH
3OCH
3CH
4-OCH
3SO-cyclopropyl H OCH
3OCH
3CH
6-CH
3SO-cyclopropyl H OCH
3OCH
3CH
6-OCH
3SO-cyclopropyl H OCH
3OCH
3CH
6-F SO-cyclopropyl H OCH
3OCH
3CH
6-Cl SO-cyclopropyl H OCH
3OCH
3CH
H SO
2-cyclopropyl H OCH
3OCH
3CH
H SO
2-cyclopropyl H OCH
3CH
3CH
H SO
2-cyclopropyl H Cl OCH
3CH
H SO
2-cyclopropyl H CH
3CH
3CH
H SO
2-cyclopropyl H OCH
3OCH
3N
H SO
2-cyclopropyl H OCH
3CH
3N
H SO
2-cyclopropyl H OCH
2CH
3NHCH
3N
H SO
2-cyclopropyl CH
3OCH
3CH
3N
4-CH
3SO
2-cyclopropyl H OCH
3OCH
3CH
4-OCH
3SO
2-cyclopropyl H OCH
3OCH
3CH
6-CH
3SO
2-cyclopropyl H OCH
3OCH
3CH
6-OCH
3SO
2-cyclopropyl H OCH
3OCH
3CH
6-F SO
2-cyclopropyl H OCH
3OCH
3CH
6-Cl SO
2-cyclopropyl H OCH
3OCH
3CH
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
6-F SO
2CH
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-Cl SO
2CH
2CH
2CH
2CH
3H OCH
3OCH
3CH
H S-cyclopropyl H OCH
3OCH
3CH
H S-cyclopropyl H OCH
3CH
3CH
H S-cyclopropyl H Cl OCH
3CH
H S-cyclopropyl H CH
3CH
3CH
H S-cyclopropyl H OCH
3OCH
3N
H S-cyclopropyl H OCH
3CH
3N
H S-cyclopropyl H OCH
2CH
3NHCH
3N
H S-cyclopropyl CH
3OCH
3CH
3N
4-CH
3S-cyclopropyl H OCH
3OCH
3CH
4-OCH
3S-cyclopropyl H OCH
3OCH
3CH
6-CH
3S-cyclopropyl H OCH
3OCH
3CH
6-OCH
3S-cyclopropyl H OCH
3OCH
3CH
6-F S-cyclopropyl H OCH
3OCH
3CH
6-Cl S-cyclopropyl H OCH
3OCH
3CH
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
H OSO
2CH
3H OCH
3OCH
3CH 169-171
H OSO
2CH
3H OCH
3CH
3CH 172-173.5
H OSO
2CH
3H Cl OCH
3CH 171-173
H OSO
2CH
3H CH
3CH
3CH 161.5-165
H OSO
2CH
3H OCH
3OCH
3N
H OSO
2CH
3H OCH
3CH
3N 155-158
H OSO
2CH
3H OCH
2CH
3NHCH
3N
H OSO
2CH
3CH
3OCH
3CH
3N
4-CH
3OSO
2CH
3H OCH
3OCH
3CH
4-OCH
3OSO
2CH
3H OCH
3OCH
3CH
6-CH
3OSO
2CH
3H OCH
3OCH
3CH
6-OCH
3OSO
2CH
3H OCH
3OCH
3CH
6-F OSO
2CH
3H OCH
3OCH
3CH
6-Cl OSO
2CH
3H OCH
3OCH
3CH
H OSO
2CH
2CH
3H OCH
3OCH
3CH 162-163.5
H OSO
2CH
2CH
3H OCH
3CH
3CH 160-162
H OSO
2CH
2CH
3H Cl OCH
3CH 139-143
H OSO
2CH
2CH
3H CH
3CH
3CH 132-138
H OSO
2CH
2CH
3H OCH
3OCH
3N 171.5-173
H OSO
2CH
2CH
3H OCH
3CH
3N 147-149
H OSO
2CH
2CH
3H OCH
2CH
3NHCH
3N
H OSO
2CH
2CH
3CH
3OCH
3CH
3N
4-CH
3OSO
2CH
2CH
3H OCH
3OCH
3CH
4-OCH
3OSO
2CH
2CH
3H OCH
3OCH
3CH
6-CH
3OSO
2CH
2CH
3H OCH
3OCH
3CH
6-OCH
3OSO
2CH
2CH
3H OCH
3OCH
3CH
6-F OSO
2CH
2CH
3H OCH
3OCH
3CH
6-Cl OSO
2CH
2CH
3H OCH
3OCH
3CH
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
H OSO
2CH
2CH
2CH
3H OCH
3OCH
3CH 156-157
H OSO
2CH
2CH
2CH
3H OCH
3CH
3CH 131-133
H OSO
2CH
2CH
2CH
3H Cl OCH
3CH 127-132
H OSO
2CH
2CH
2CH
3H CH
3CH
3CH 152-153
H OSO
2CH
2CH
2CH
3H OCH
3OCH
3N 154-155
H OSO
2CH
2CH
2CH
3H OCH
3CH
3N
H OSO
2CH
2CH
2CH
3H OCH
2CH
3NHCH
3N
H OSO
2CH
2CH
2CH
3CH
3OCH
3CH
3N
4-CH
3OSO
2CH
2CH
2CH
3H OCH
3OCH
3CH
4-OCH
3OSO
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-CH
3OSO
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-OCH
3OSO
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-F OSO
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-Cl OSO
2CH
2CH
2CH
3H OCH
3OCH
3CH
H OSO
2CH(CH
3)
2H OCH
3OCH
3CH
H OSO
2CH(CH
3)
2H OCH
3CH
3CH
H OSO
2CH(CH
3)
2H Cl OCH
3CH
H OSO
2CH(CH
3)
2H CH
3CH
3CH
H OSO
2CH(CH
3)
2H OCH
3OCH
3N
H OSO
2CH(CH
3)
2H OCH
3CH
3N
H OSO
2CH(CH
3)
2H OCH
2CH
3NHCH
3N
H OSO
2CH(CH
3)
2CH
3OCH
3CH
3N
4-CH
3OSO
2CH(CH
3)
2H OCH
3OCH
3CH
4-OCH
3OSO
2CH(CH
3)
2H OCH
3OCH
3CH
6-CH
3OSO
2CH(CH
3)
2H OCH
3OCH
3CH
6-OCH
3OSO
2CH(CH
3)
2H OCH
3OCH
3CH
6-F OSO
2CH(CH
3)
2H OCH
3OCH
3CH
6-Cl OSO
2CH(CH
3)
2H OCH
3OCH
3CH
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
H OSO
2CH
2CH
2CH
2CH
3H OCH
3OCH
3CH
H OSO
2CH
2CH
2CH
2CH
3H OCH
3CH
3CH
H OSO
2CH
2CH
2CH
2CH
3H Cl OCH
3CH
H OSO
2CH
2CH
2CH
2CH
3H CH
3CH
3CH
H OSO
2CH
2CH
2CH
2CH
3H OCH
3OCH
3N
H OSO
2CH
2CH
2CH
2CH
3H OCH
3CH
3N
H OSO
2CH
2CH
2CH
2CH
3H OCH
2CH
3NHCH
3N
H OSO
2CH
2CH
2CH
2CH
3CH
3OCH
3CH
3N
4-CH
3OSO
2CH
2CH
2CH
2CH
3H OCH
3OCH
3CH
4-OCH
3OSO
2CH
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-CH
3OSO
2CH
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-OCH
3OSO
2CH
2CH
2CH
2CH
3H OCH
3OCH CH
6-F OSO
2CH
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-Cl OSO
2CH
2CH
2CH
2CH
3H OCH
3OCH
3CH
H OSO
2CF
3H OCH
3OCH
3CH 140-142
H OSO
2CF
3H OCH
3CH
3CH
H OSO
2CF
3H Cl OCH
3CH 154-156
H OSO
2CF
3H CH
3CH
3CH 157-160
H OSO
2CF
3H OCH
3OCH
3N 164-166
H OSO
2CF
3H OCH
3CH
3N 157-159
H OSO
2CF
3H OCH
2CH
3NHCH
3N
H OSO
2CF
3CH
3OCH
3CH
3N
4-CH
3OSO
2CF
3H OCH
3OCH
3CH
4-OCH
3OSO
2CF
3H OCH
3OCH
3CH
6-CH
3OSO
2CF
3H OCH
3OCH
3CH
6-OCH
3OSO
2CF
3H OCH
3OCH
3CH
6-F OSO
2CF
3H OCH
3OCH
3CH
6-Cl OSO
2CF
3H OCH
3OCH
3CH
Table I (continuing)
R
1R
2R X Y Z m.p.(℃
H OSO
2CCl
3H OCH
3OCH
3CH
H OSO
2CCl
3H OCH
3CH
3CH
H OSO
2CCl
3H Cl OCH
3CH
H OSO
2CCl
3H CH
3CH
3CH
H OSO
2CCl
3H OCH
3OCH
3N
H OSO
2CCl
3H OCH
3CH
3N
H OSO
2CCl
3H OCH
2CH
3NHCH
3N
H OSO
2CCl
3CH
3OCH
3CH
3N
4-CH
3OSO
2CCl
3H OCH
3OCH
3CH
4-OCH
3OSO
2CCl
3H OCH
3OCH
3CH
6-CH
3OSO
2CCl
3H OCH
3OCH
3CH
6-OCH
3OSO
2CCl
3H OCH
3OCH
3CH
6-F OSO
2CCl
3H OCH
3OCH
3CH
6-Cl OSO
2CCl
3H OCH
3OCH
3CH
H OSO
2CH
2CH
2CH
2Cl H OCH
3OCH
3CH
H OSO
2CH
2CH
2CH
2Cl H OCH
3CH
3CH
H OSO
2CH
2CH
2CH
2Cl H Cl OCH
3CH
H OSO
2CH
2CH
2CH
2Cl H CH
3CH
3CH
H OSO
2CH
2CH
2CH
2Cl H OCH
3OCH
3N
H OSO
2CH
2CH
2CH
2Cl H OCH
3CH
3N
H OSO
2CH
2CH
2CH
2Cl H OCH
2CH
3NHCH
3N
H OSO
2CH
2CH
2CH
2Cl CH
3OCH
3CH
3N
4-CH
3OSO
2CH
2CH
2CH
2Cl H OCH
3OCH
3CH
4-OCH
3OSO
2CH
2CH
2CH
2Cl H OCH
3OCH
3CH
6-CH
3OSO
2CH
2CH
2CH
2Cl H OCH
3OCH
3CH
6-OCH
3OSO
2CH
2CH
2CH
2Cl H OCH
3OCH
3CH
6-F OSO
2CH
2CH
2CH
2Cl H OCH
3OCH
3CH
6-Cl OSO
2CH
2CH
2CH
2Cl H OCH
3OCH
3CH
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
H SO
2OCH
2CF
3H OCH
3OCH
3CH
H SO
2OCH
2CF
3H OCH
3CH
3CH
H SO
2OCH
2CF
3H Cl OCH
3CH
H SO
2OCH
2CF
3H CH
3CH
3CH
H SO
2OCH
2CF
3H OCH
3OCH
3N
H SO
2OCH
2CF
3H OCH
3CH
3N
H SO
2OCH
2CF
3H OCH
2CH
3NHCH
3N
H SO
2OCH
2CF
3CH
3OCH
3CH
3N
4-CH
3SO
2OCH
2CF
3H OCH
3OCH
3CH
4-OCH
3SO
2OCH
2CF
3H OCH
3OCH
3CH
6-CH
3SO
2OCH
2CF
3H OCH
3OCH
3CH
6-OCH
3SO
2OCH
2CF
3H OCH
3OCH
3CH
6-F SO
2OCH
2CF
3H OCH
3OCH
3CH
6-Cl SO
2OCH
2CF
3H OCH
3OCH
3CH
H SO
2OCH
3H OCH
3OCH
3CH
H SO
2OCH
3H OCH
3CH
3CH
H SO
2OCH
3H Cl OCH
3CH
H SO
2OCH
3H CH
3CH
3CH
H SO
2OCH
3H OCH
3OCH
3N
H SO
2OCH
3H OCH
3CH
3N
H SO
2OCH
3H OCH
2CH
3NHCH
3N
H SO
2OCH
3CH
3OCH
3CH
3N
4-CH
3SO
2OCH
3H OCH
3OCH
3CH
4-OCH
3SO
2OCH
3H OCH
3OCH
3CH
6-CH
3SO
2OCH
3H OCH
3OCH
3CH
6-OCH
3SO
2OCH
3H OCH
3OCH
3CH
6-F SO
2OCH
3H OCH
3OCH
3CH
6-Cl SO
2OCH
3H OCH
3OCH
3CH
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
H SO
2OCH
2CH
3H OCH
3OCH
3CH
H SO
2OCH
2CH
3H OCH
3CH
3CH
H SO
2OCH
2CH
3H Cl OCH
3CH
H SO
2OCH
2CH
3H CH
3CH
3CH
H SO
2OCH
2CH
3H OCH
3OCH
3N
H SO
2OCH
2CH
3H OCH
3CH
3N
H SO
2OCH
2CH
3H OCH
2CH
3NHCH
3N
H SO
2OCH
2CH
3CH
3OCH
3CH
3N
4-CH
3SO
2OCH
2CH
3H OCH
3OCH
3CH
4-OCH
3SO
2OCH
2CH
3H OCH
3OCH
3CH
6-CH
3SO
2OCH
2CH
3H OCH
3OCH
3CH
6-OCH
3SO
2OCH
2CH
3H OCH
3OCH
3CH
6-F SO
2OCH
2CH
3H OCH
3OCH
3CH
6-Cl SO
2OCH
2CH
3H OCH
3OCH
3CH
H N
3H OCH
3OCH
3CH
H N
3H OCH
3CH
3CH
H N
3H Cl OCH
3CH
H N
3H CH
3CH
3CH
H N
3H OCH
3OCH
3N
H N
3H OCH
3CH
3N
H N
3H OCH
2CH
3NHCH
3N
H N
3CH
3OCH
3CH
3N
4-CH
3N
3H OCH
3OCH
3CH
4-OCH
3N
3H OCH
3OCH
3CH
6-CH
3N
3H OCH
3OCH
3CH
6-OCH
3N
3H OCH
3OCH
3CH
6-F N
3H OCH
3OCH
3CH
6-Cl N
3H OCH
3OCH
3CH
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
H CN H OCH
3OCH
3CH
H CN H OCH
3CH
3CH
H CN H Cl OCH
3CH
H CN H CH
3CH
3CH
H CN H OCH
3OCH
3N
H CN H OCH
3CH
3N
H CN H OCH
2CH
3NHCH
3N
H CN CH
3OCH
3CH
3N
4-CH
3CN H OCH
3OCH
3CH
4-OCH
3CN H OCH
3OCH
3CH
6-CH
3CN H OCH
3OCH
3CH
6-OCH
3CN H OCH
3OCH
3CH
6-F CN H OCH
3OCH
3CH
6-Cl CN H OCH
3OCH
3CH
H P(O)(OCH
3)
2H OCH
3OCH
3CH
H P(O)(OCH
3)
2H OCH
3CH
3CH
H P(O)(OCH
3)
2H Cl OCH
3CH
H P(O)(OCH
3)
2H CH
3CH
3CH
H P(O)(OCH
3)
2H OCH
3OCH
3N
H P(O)(OCH
3)
2H OCH
3CH
3N
H P(O)(OCH
3)
2H OCH
2CH
3NHCH
3N
H P(O)(OCH
3)
2CH
3OCH
3CH
3N
4-CH
3P(O)(OCH
3)
2H OCH
3OCH
3CH
4-OCH
3P(O)(OCH
3)
2H OCH
3OCH
3CH
6-CH
3P(O)(OCH
3)
2H OCH
3OCH
3CH
6-OCH
3P(O)(OCH
3)
2H OCH
3OCH
3CH
6-F P(O)(OCH
3)
2H OCH
3OCH
3CH
6-Cl P(O)(OCH
3)
2H OCH
3OCH
3CH
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
H P(O)(OCH
2CH
3)
2H OCH
3OCH
3CH 108-111
H P(O)(OCH
2CH
3)
2H OCH
3CH
3CH
H P(O)(OCH
2CH
3)
2H Cl OCH
3CH
H P(O)(OCH
2CH
3)
2H CH
3CH
3CH 110-114
H P(O)(OCH
2CH
3)
2H OCH
3OCH
3N
H P(O)(OCH
2CH
3)
2H OCH
3CH
3N
H P(O)(OCH
2CH
3)
2H OCH
2CH
3NHCH
3N
H P(O)(OCH
2CH
3)
2CH
3OCH
3CH
3N
4-CH
3P(O)(OCH
2CH
3)
2H OCH
3OCH
3CH
4-OCH
3P(O)(OCH
2CH
3)
2H OCH
3OCH
3CH
6-CH
3P(O)(OCH
2CH
3)
2H OCH
3OCH
3CH
6-OCH
3P(O)(OCH
2CH
3)
2H OCH
3OCH
3CH
6-F P(O)(OCH
2CH
3)
2H OCH
3OCH
3CH
6-Cl P(O)(OCH
2CH
3)
2H OCH
3OCH
3CH
H P(S)(OCH
3)
2H OCH
3OCH
3CH
H P(S)(OCH
3)
2H OCH
3CH
3CH
H P(S)(OCH
3)
2H Cl OCH
3CH
H P(S)(OCH
3)
2H CH
3CH
3CH
H P(S)(OCH
3)
2H OCH
3OCH
3N
H P(S)(OCH
3)
2H OCH
3CH
3N
H P(S)(OCH
3)
2H OCH
2CH
3NHCH
3N
H P(S)(OCH
3)
2CH
3OCH
3CH
3N
4-CH
3P(S)(OCH
3)
2H OCH
3OCH
3CH
4-OCH
3P(S)(OCH
3)
2H OCH
3OCH
3CH
6-CH
3P(S)(OCH
3)
2H OCH
3OCH
3CH
6-OCH
3P(S)(OCH
3)
2H OCH
3OCH
3CH
6-F P(S)(OCH
3)
2H OCH
3OCH
3CH
6-Cl P(S)(OCH
3)
2H OCH
3OCH
3CH
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
H P(S)(OCH
2CH
3)
2H OCH
3OCH
3CH
H P(S)(OCH
2CH
3)
2H OCH
3CH
3CH
H P(S)(OCH
2CH
3)
2H Cl OCH
3CH
H P(S)(OCH
2CH
3)
2H CH
3CH
3CH
H P(S)(OCH
2CH
3)
2H OCH
3OCH
3N
H P(S)(OCH
2CH
3)
2H OCH
3CH
3N
H P(S)(OCH
2CH
3)
2H OCH
2CH
3NHCH
3N
H P(S)(OCH
2CH
3)
2CH
3OCH
3CH
3N
4-CH
3P(S)(OCH
2CH
3)
2H OCH
3OCH
3CH
4-OCH
3P(S)(OCH
2CH
3)
2H OCH
3OCH
3CH
6-CH
3P(S)(OCH
2CH
3)
2H OCH
3OCH
3CH
6-OCH
3P(S)(OCH
2CH
3)
2H OCH
3OCH
3CH
6-F P(S)(OCH
2CH
3)
2H OCH
3OCH
3CH
6-Cl P(S)(OCH
2CH
3)
2H OCH
3OCH
3CH
H CH
2F H OCH
3OCH
3CH
H CH
2F H OCH
3CH
3CH
H CH
2F H Cl OCH
3CH
H CH
2F H CH
3CH
3CH
H CH
2F H OCH
3OCH
3N
H CH
2F H OCH
3CH
3N
H CH
2F H OCH
2CH
3NHCH
3N
H CH
2F CH
3OCH
3CH
3N
4-CH
3CH
2F H OCH
3OCH
3CH
4-OCH
3CH
2F H OCH
3OCH
3CH
6-CH
3CH
2F H OCH
3OCH
3CH
6-OCH
3CH
2F H OCH
3OCH
3CH
6-F CH
2F H OCH
3OCH
3CH
6-Cl CH
2F H OCH
3OCH
3CH
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
H CF
2H H OCH
3OCH
3CH
H CF
2H H OCH
3CH
3CH
H CF
2H H Cl OCH
3CH
H CF
2H H CH
3CH
3CH
H CF
2H H OCH
3OCH
3N
H CF
2H H OCH
3CH
3N
H CF
2H H OCH
2CH
3NHCH
3N
H CF
2H CH
3OCH
3CH
3N
4-CH
3CF
2H H OCH
3OCH
3CH
4-OCH
3CF
2H H OCH
3OCH
3CH
6-CH
3CF
2H H OCH
3OCH
3CH
6-OCH
3CF
2H H OCH
3OCH
3CH
6-F CF
2H H OCH
3OCH
3CH
6-Cl CF
2H H OCH
3OCH
3CH
H CH
2Cl H OCH
3OCH
3CH
H CH
2Cl H OCH
3CH
3CH
H CH
2Cl H Cl OCH
3CH
H CH
2Cl H CH
3CH
3CH
H CH
2Cl H OCH
3OCH
3N
H CH
2Cl H OCH
3CH
3N
H CH
2Cl H OCH
2CH
3NHCH
3N
H CH
2Cl CH
3OCH
3CH
3N
4-CH
3CH
2Cl H OCH
3OCH
3CH
4-OCH
3CH
2Cl H OCH
3OCH
3CH
6-CH
3CH
2Cl H OCH
3OCH
3CH
6-OCH
3CH
2Cl H OCH
3OCH
3CH
6-F CH
2Cl H OCH
3OCH
3CH
6-Cl CH
2Cl H OCH
3OCH
3CH
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
H CCl
2H H OCH
3OCH
3CH
H CCl
2H H OCH
3CH
3CH
H CCl
2H H Cl OCH
3CH
H CCl
2H H CH
3CH
3CH
H CCl
2H H OCH
3OCH
3N
H CCl
2H H OCH
3CH
3N
H CCl
2H H OCH
2CH
3NHCH
3N
H CCl
2H CH
3OCH
3CH
3N
4-CH
3CCl
2H H OCH
3OCH
3CH
4-OCH
3CCl
2H H OCH
3OCH
3CH
6-CH
3CCl
2H H OCH
3OCH
3CH
6-OCH
3CCl
2H H OCH
3OCH
3CH
6-F CCl
2H H OCH
3OCH
3CH
6-Cl CCl
2H H OCH
3OCH
3CH
H CH
2CH
2Cl H OCH
3OCH
3CH
H CH
2CH
2Cl H OCH
3CH
3CH
H CH
2CH
2Cl H Cl OCH
3CH
H CH
2CH
2Cl H CH
3CH
3CH
H CH
2CH
2Cl H OCH
3OCH
3N
H CH
2CH
2Cl H OCH
3CH
3N
H CH
2CH
2Cl H OCH
2CH
3NHCH
3N
H CH
2CH
2Cl CH
3OCH
3CH
3N
4-CH
3CH
2CH
2Cl H OCH
3OCH
3CH
4-OCH
3CH
2CH
2Cl H OCH
3OCH
3CH
6-CH
3CH
2CH
2Cl H OCH
3OCH
3CH
6-OCH
3CH
2CH
2Cl H OCH
3OCH
3CH
6-F CH
2CH
2Cl H OCH
3OCH
3CH
6-Cl CH
2CH
2Cl H OCH
3OCH
3CH
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
H CH
2CH
2Br H OCH
3OCH
3CH
H CH
2CH
2Br H OCH
3CH
3CH
H CH
2CH
2Br H Cl OCH
3CH
H CH
2CH
2Br H CH
3CH
3CH
H CH
2CH
2Br H OCH
3OCH
3N
H CH
2CH
2Br H OCH
3CH
3N
H CH
2CH
2Br H OCH
2CH
3NHCH
3N
H CH
2CH
2Br CH
3OCH
3CH
3N
4-CH
3CH
2CH
2Br H OCH
3OCH
3CH
4-OCH
3CH
2CH
2Br H OCH
3OCH
3CH
6-CH
3CH
2CH
2Br H OCH
3OCH
3CH
6-OCH
3CH
2CH
2Br H OCH
3OCH
3CH
6-F CH
2CH
2Br H OCH
3OCH
3CH
6-Cl CH
2CH
2Br H OCH
3OCH
3CH
H CHFCH
3H OCH
3OCH
3CH
H CHFCH
3H OCH
3CH
3CH
H CHFCH
3H Cl OCH
3CH
H CHFCH
3H CH
3CH
3CH
H CHFCH
3H OCH
3OCH
3N
H CHFCH
3H OCH
3CH
3N
H CHFCH
3H OCH
2CH
3NHCH
3N
H CHFCH
3CH
3OCH
3CH
3N
4-CH
3CHFCH
3H OCH
3OCH
3CH
4-OCH
3CHFCH
3H OCH
3OCH
3CH
6-CH
3CHFCH
3H OCH
3OCH
3CH
6-OCH
3CHFCH
3H OCH
3OCH
3CH
6-F CHFCH
3H OCH
3OCH
3CH
6-Cl CHFCH
3H OCH
3OCH
3CH
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
H CHClCH
3H OCH
3OCH
3CH
H CHClCH
3H OCH
3CH
3CH
H CHClCH
3H Cl OCH
3CH
H CHClCH
3H CH
3CH
3CH
H CHClCH
3H OCH
3OCH
3N
H CHClCH
3H OCH
3CH
3N
H CHClCH
3H OCH
2CH
3NHCH
3N
H CHClCH
3CH
3OCH
3CH
3N
4-CH
3CHClCH
3H OCH
3OCH
3CH
4-OCH
3CHClCH
3H OCH
3OCH
3CH
6-CH
3CHClCH
3H OCH
3OCH
3CH
6-OCH
3CHClCH
3H OCH
3OCH
3CH
6-F CHClCH
3H OCH
3OCH
3CH
6-Cl CHClCH
3H OCH
3OCH
3CH
H CF
2CF
2H H OCH
3OCH
3CH
H CF
2CF
2H H OCH
3CH
3CH
H CF
2CF
2H H Cl OCH
3CH
H CF
2CF
2H H CH
3CH
3CH
H CF
2CF
2H H OCH
3OCH
3N
H CF
2CF
2H H OCH
3CH
3N
H CF
2CF
2H H OCH
2CH
3NHCH
3N
H CF
2CF
2H CH
3OCH
3CH
3N
4-CH
3CF
2CF
2H H OCH
3OCH
3CH
4-OCH
3CF
2CF
2H H OCH
3OCH
3CH
6-CH
3CF
2CF
2H H OCH
3OCH
3CH
6-OCH
3CF
2CF
2H H OCH
3OCH
3CH
6-F CF
2CF
2H H OCH
3OCH
3CH
6-Cl CF
2CF
2H H OCH
3OCH
3CH
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
6-CH
2CH
3SO
2N(CH
3)
2H OCH
3OCH
3CH
6-CH
2CH
3SO
2N(CH
3)
2H OCH
3CH
3CH
6-CH
2CH
3SO
2N(CH
3)
2H Cl OCH
3CH
6-CH
2CH
3SO
2N(CH
3)
2H CH
3CH
3CH
6-CH
2CH
3SO
2N(CH
3)
2H OCH
3OCH
3N
6-CH
2CH
3SO
2N(CH
3)
2H OCH
3CH
3N
6-CH
2CH
3SO
2N(CH
3)
2H OCH
2CH
3NHCH
3N
6-CH
2CH
3SO
2N(CH
3)
2CH
3OCH
2CH
3CH
3N
6-OCH
3SO
2N(CH
3)
2H OCH
3OCH
3CH
6-OCH
3SO
2N(CH
3)
2H OCH
3CH
3CH
6-OCH
3SO
2N(CH
3)
2H Cl OCH
3CH
6-OCH
3SO
2N(CH
3)
2H CH
3CH
3CH
6-OCH
3SO
2N(CH
3)
2H OCH
3OCH
3N
6-OCH
3SO
2N(CH
3)
2H OCH
3CH
3N
6-OCH
3SO
2N(CH
3)
2H OCH
2CH
3NHCH
3N
6-OCH
3SO
2N(CH
3)
2CH
3OCH
3CH
3N
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
6-OCH
2CH
3SO
2N(CH
3)
2H OCH
3OCH
3CH
6-OCH
2CH
3SO
2N(CH
3)
2H OCH
3CH
3CH
6-OCH
2CH
3SO
2N(CH
3)
2H Cl OCH
3CH
6-OCH
2CH
3SO
2N(CH
3)
2H CH
3CH
3CH
6-OCH
2CH
3SO
2N(CH
3)
2H OCH
3OCH
3N
6-OCH
2CH
3SO
2N(CH
3)
2H OCH
3CH
3N
6-OCH
2CH
3SO
2N(CH
3)
2H OCH
2CH
3NHCH
3N
6-OCH
2CH
3SO
2N(CH
3)
2CH
3OCH
3CH
3N
6-SCH
2CH
3SO
2N(CH
3)
2H OCH
3OCH
3CH
6-SCH
2CH
3SO
2N(CH
3)
2H OCH
3CH
3CH
6-SCH
2CH
3SO
2N(CH
3)
2H Cl OCH
3CH
6-SCH
2CH
3SO
2N(CH
3)
2H CH
3CH
3CH
6-SCH
2CH
3SO
2N(CH
3)
2H OCH
3OCH
3N
6-SCH
2CH
3SO
2N(CH
3)
2H OCH
3CH
3N
6-SCH
2CH
3SO
2N(CH
3)
2H OCH
2CH
3NHCH
3N
6-SCH
2CH
3SO
2N(CH
3)
2CH
3OCH
3CH
3N
6-SCH
3SO
2N(CH
3)
2H OCH
3OCH
3CH
6-SCH
3SO
2N(CH
3)
2H OCH
3CH
3CH
6-SCH
3SO
2N(CH
3)
2H Cl OCH
3CH
6-SCH
3SO
2N(CH
3)
2H CH
3CH
3CH
6-SCH
3SO
2N(CH
3)
2H OCH
3OCH
3N
6-SCH
3SO
2N(CH
3)
2H OCH
3CH
3N
6-SCH
3SO
2N(CH
3)
2H OCH
2CH
3NHCH
3N
6-SCH
3SO
2N(CH
3)
2CH
3OCH
3CH
3N
6-N(CH
3)
2SO
2N(CH
3)
2H OCH
3OCH
3CH
6-N(CH
3)
2SO
2N(CH
3)
2H OCH
3CH
3CH
6-N(CH
3)
2SO
2N(CH
3)
2H Cl OCH
3CH
6-N(CH
3)
2SO
2N(CH
3)
2H CH
3CH
3CH
6-N(CH
3)
2SO
2N(CH
3)
2H OCH
3OCH
3N
6-N(CH
3)
2SO
2N(CH
3)
2H OCH
3CH
3N
6-N(CH
3)
2SO
2N(CH
3)
2H OCH
2CH
3NHCH
3N
6-N(CH
3)
2SO
2N(CH
3)
2CH
3OCH
3CH
3N
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
6-NHCH
3SO
2N(CH
3)
2H OCH
3OCH
3CH
6-NHCH
3SO
2N(CH
3)
2H OCH
3CH
3CH
6-NHCH
3SO
2N(CH
3)
2H Cl OCH
3CH
6-NHCH
3SO
2N(CH
3)
2H CH
3CH
3CH
6-NHCH
3SO
2N(CH
3)
2H OCH
3OCH
3N
6-NHCH
3SO
2N(CH
3)
2H OCH
3CH
3N
6-NHCH
3SO
2N(CH
3)
2H OCH
2CH
3NHCH
3N
6-NHCH
3SO
2N(CH
3)
2CH
3OCH
3CH
3N
6-OCH
3SO
2N(CH
2CH
3)
2H OCH
3OCH
3CH
6-OCH
3SO
2N(CH
2CH
3)
2H OCH
3CH
3CH
6-OCH
3SO
2N(CH
2CH
3)
2H Cl OCH
3CH
6-OCH
3SO
2N(CH
2CH
3)
2H CH
3CH
3CH
6-OCH
3SO
2N(CH
2CH
3)
2H OCH
3OCH
3N
6-OCH
3SO
2N(CH
2CH
3)
2H OCH
3CH
3N
6-OCH
3SO
2N(CH
2CH
3)
2H OCH
2CH
3NHCH
3N
6-OCH
3SO
2N(CH
2CH
3)
2CH
3OCH
3CH
3N
6-SCH
3SO
2N(CH
2CH
3)
2H OCH
3OCH
3CH
6-SCH
3SO
2N(CH
2CH
3)
2H OCH
3CH
3CH
6-SCH
3SO
2N(CH
2CH
3)
2H Cl OCH
3CH
6-SCH
3SO
2N(CH
2CH
3)
2H CH
3CH
3CH
6-SCH
3SO
2N(CH
2CH
3)
2H OCH
3OCH
3N
6-SCH
3SO
2N(CH
2CH
3)
2H OCH
3CH
3N
6-SCH
3SO
2N(CH
2CH
3)
2H OCH
2CH
3NHCH
3N
6-SCH
3SO
2N(CH
2CH
3)
2CH
3OCH
3CH
3N
6-N(CH
3)
2SO
2N(CH
2CH
3)
2H OCH
3OCH
3CH
6-N(CH
3)
2SO
2N(CH
2CH
3)
2H OCH
3CH
3CH
6-N(CH
3)
2SO
2N(CH
2CH
3)
2H Cl OCH
3CH
6-N(CH
3)
2SO
2N(CH
2CH
3)
2H CH
3CH
3CH
6-N(CH
3)
2SO
2N(CH
2CH
3)
2H OCH
3OCH
3N
6-N(CH
3)
2SO
2N(CH
2CH
3)
2H OCH
3CH
3N
6-N(CH
3)
2SO
2N(CH
2CH
3)
2H OCH
2CH
3NHCH
3N
6-N(CH
3)
2SO
2N(CH
2CH
3)
2CH
3OCH
3CH
3N
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
6-SCH
3SO
2NHOCH
3H OCH
3OCH
3CH
6-SCH
3SO
2NHOCH
3H OCH
3CH
3CH
6-SCH
3SO
2NHOCH
3H Cl OCH
3CH
6-SCH
3SO
2NHOCH
3H CH
3CH
3CH
6-SCH
3SO
2NHOCH
3H OCH
3OCH
3N
6-SCH
3SO
2NHOCH
3H OCH
3CH
3N
6-SCH
3SO
2NHOCH
3H OCH
2CH
3NHCH
3N
6-SCH
3SO
2NHOCH
3CH
3OCH
3CH
3N
6-SCH
2CH
3SO
2NHOCH
3H OCH
3OCH
3CH
6-SCH
2CH
3SO
2NHOCH
3H OCH
3CH
3CH
6-SCH
2CH
3SO
2NHOCH
3H Cl OCH
3CH
6-SCH
2CH
3SO
2NHOCH
3H CH
3CH
3CH
6-SCH
2CH
3SO
2NHOCH
3H OCH
3OCH
3N
6-SCH
2CH
3SO
2NHOCH
3H OCH
3CH
3N
6-SCH
2CH
3SO
2NHOCH
3H OCH
2CH
3NHCH
3N
6-SCH
2CH
3SO
2NHOCH
3CH
3OCH
3CH
3N
6-N(CH
3)
2SO
2NHOCH
3H OCH
3OCH
3CH
6-N(CH
3)
2SO
2NHOCH
3H OCH
3CH
3CH
6-N(CH
3)
2SO
2NHOCH
3H Cl OCH
3CH
6-N(CH
3)
2SO
2NHOCH
3H CH
3CH
3CH
6-N(CH
3)
2SO
2NHOCH
3H OCH
3OCH
3N
6-N(CH
3)
2SO
2NHOCH
3H OCH
3CH
3N
6-N(CH
3)
2SO
2NHOCH
3H OCH
2CH
3NHCH
3N
6-N(CH
3)
2SO
2NHOCH
3CH
3OCH
3CH
3N
6-OCH
3SO
2NHOCH
3H OCH
3OCH
3CH
6-OCH
3SO
2NHOCH
3H OCH
3CH
3CH
6-OCH
3SO
2NHOCH
3H Cl OCH
3CH
6-OCH
3SO
2NHOCH
3H CH
3CH
3CH
6-OCH
3SO
2NHOCH
3H OCH
3OCH
3N
6-OCH
3SO
2NHOCH
3H OCH
3CH
3N
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
6-OCH
3SO
2NHOCH
3H OCH
2CH
3NHCH
3N
6-OCH
3SO
2NHOCH
3CH
3OCH
3CH
3N
6-OCH
3SO
2NHCH
3H OCH
3OCH
3CH
6-OCH
3SO
2NHCH
3H OCH
3CH
3CH
6-OCH
3SO
2NHCH
3H Cl OCH
3CH
6-OCH
3SO
2NHCH
3H CH
3CH
3CH
6-OCH
3SO
2NHCH
3H OCH
3OCH
3N
6-OCH
3SO
2NHCH
3H OCH
3CH
3N
6-OCH
3SO
2NHCH
3H OCH
2CH
3NHCH
3N
6-OCH
3SO
2NHCH
3CH
3OCH
3CH
3N
6-SCH
3SO
2NHCH
3H OCH
3OCH
3CH
6-SCH
3SO
2NHCH
3H OCH
3CH
3CH
6-SCH
3SO
2NHCH
3H Cl OCH
3CH
6-SCH
3SO
2NHCH
3H CH
3CH
3CH
6-SCH
3SO
2NHCH
3H OCH
3OCH
3N
6-SCH
3SO
2NHCH
3H OCH
3CH
3N
6-SCH
3SO
2NHCH
3H OCH
2CH
3NHCH
3N
6-SCH
3SO
2NHCH
3CH
3OCH
3CH
3N
H SO
2NHCH
3H OCH
3OCH
3CH 147-148.5
H SO
2NHCH
3H OCH
3CH
3CH
H SO
2NHCH
3H Cl OCH
3CH 155-157
H SO
2NHCH
3H CH
3CH
3CH 150-152
H SO
2NHCH
3H OCH
3OCH
3N
H SO
2NHCH
3H OCH
3CH
3N 153.5-155
H SO
2NHCH
3H OCH
2CH
3NHCH
3N
H SO
2NHCH
3CH
3OCH
3CH
3N
4-CH
3SO
2NHCH
3H OCH
3OCH
3CH
4-OCH
3SO
2NHCH
3H OCH
3OCH
3CH
6-CH
3SO
2NHCH
3H OCH
3OCH
3CH
6-F SO
2NHCH
3H OCH
3OCH
3CH
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
6-Cl SO
2NHCH
3H OCH
3OCH
3CH
H SO
2NHCH
2CH
3H OCH
3OCH
3CH 163-165.5
H SO
2NHCH
2CH
3H OCH
3CH
3CH
H SO
2NHCH
2CH
3H Cl OCH
3CH 158.5-161
H SO
2NHCH
2CH
3H CH
3CH
3CH 118-121.5
H SO
2NHCH
2CH
3H OCH
3OCH
3N 162-164
H SO
2NHCH
2CH
3H OCH
3CH
3N 158-160
H SO
2NHCH
2CH
3H OCH
2CH
3NHCH
3N
H SO
2NHCH
2CH
3CH
3OCH
3CH
3N 122-125.5
4-CH
3SO
2NHCH
2CH
3H OCH
3OCH
3CH
4-OCH
3SO
2NHCH
2CH
3H OCH
3OCH
3CH
6-CH
3SO
2NHCH
2CH
3H OCH
3OCH
3CH
6-OCH
3SO
2NHCH
2CH
3H OCH
3OCH
3CH
6-F SO
2NHCH
2CH
3H OCH
3OCH
3CH
6-Cl SO
2NHCH
2CH
3H OCH
3OCH
3CH
H SO
2NHCH
2CH
2CH
3H OCH
3OCH
3CH 138.5-141
H SO
2NHCH
2CH
2CH
3H OCH
3CH
3CH 117-120
H SO
2NHCH
2CH
2CH
3H Cl OCH
3CH 125-129
H SO
2NHCH
2CH
2CH
3H CH
3CH
3CH
H SO
2NHCH
2CH
2CH
3H OCH
3OCH
3N 132-135
H SO
2NHCH
2CH
2CH
3H OCH
3CH
3N
H SO
2NHCH
2CH
2CH
3H OCH
2CH
3NHCH
3N
H SO
2NHCH
2CH
2CH
3CH
3OCH
3CH
3N
4-CH
3SO
2NHCH
2CH
2CH
3H OCH
3OCH
3CH
4-OCH
3SO
2NHCH
2CH
2CH
3H OCH
3OCH
3CH
6-CH
3SO
2NHCH
2CH
2CH
3H OCH
3OCH
3CH
6-OCH
3SO
2NHCH
2CH
2CH
3H OCH
3OCH
3CH
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
6-F SO
2NHCH
2CH
2CH
3H OCH
3OCH
3CH
6-Cl SO
2NHCH
2CH
2CH
3H OCH
3OCH
3CH
H SO
2NHCH(CH
3)
2H OCH
3OCH
3CH 164-166
H SO
2NHCH(CH
3)
2H OCH
3CH
3CH
3
H SO
2NHCH(CH
3)
2H Cl OCH
3CH 153.5-156
H SO
2NHCH(CH
3)
2H CH
3CH
3CH
H SO
2NHCH(CH
3)
2H OCH
3OCH
3N 149-152
H SO
2NHCH(CH
3)
2H OCH
3OCH
3N 149-151
H SO
2NHCH(CH
3)
2H OCH
2CH
3NHCH
3N
H SO
2NHCH(CH
3)
2CH
3OCH
3CH
3N 141-143
4-CH
3SO
2NHCH(CH
3)
2H OCH
3OCH
3CH
4-OCH
3SO
2NHCH(CH
3)
2H OCH
3OCH
3CH
6-CH
3SO
2NHCH(CH
3)
2H OCH
3OCH
3CH
6-OCH
3SO
2NHCH(CH
3)
2H OCH
3OCH
3CH
6-F SO
2NHCH(CH
3)
2H OCH
3OCH
3CH
6-Cl SO
2NHCH(CH
3)
2H OCH
3OCH
3CH
H SO
2NH cyclopropyl H OCH
3OCH
3CH
H SO
2NH cyclopropyl H OCH
3CH
3CH
H SO
2NH cyclopropyl H Cl OCH
3CH
H SO
2NH cyclopropyl H CH
3CH
3CH
H SO
2NH cyclopropyl H OCH
3OCH
3N
H SO
2NH cyclopropyl H OCH
3CH
3N
H SO
2NH cyclopropyl H OCH
2CH
3NHCH
3N
H SO
2NH cyclopropyl CH
3OCH
3CH
3N
4-CH
3SO
2NH cyclopropyl H OCH
3OCH
3CH
4-OCH
3SO
2NH cyclopropyl H OCH
3OCH
3CH
6-CH
3SO
2NH cyclopropyl H OCH
3OCH
3CH
6-OCH
3SO
2NH cyclopropyl H OCH
3OCH
3CH
6-F SO
2NH cyclopropyl H OCH
3OCH
3CH
6-Cl SO
2NH cyclopropyl H OCH
3OCH
3CH
H SO
2NHCH
2CH=CH
2H OCH
3OCH
3CH
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
H SO
2NHCH
2CH=CH
2H OCH
3CH
3CH
H SO
2NHCH
2CH=CH
2H CL OCH
3CH
H SO
2NHCH
2CH=CH
2H CH
3CH
3CH
H SO
2NHCH
2CH=CH
2H OCH
3OCH
3N
H SO
2NHCH
2CH=CH
2H OCH
3CH
3N
H SO
2NHCH
2CH=CH
2H OCH
2CH
3NHCH
3N
H SO
2NHCH
2CH=CH
2CH
3OCH
3CH
3N
4-CH
3SO
2NHCH
2CH=CH
2H OCH
3OCH
3CH
4-OCH
3SO
2NHCH
2CH=CH
2H OCH
3OCH
3CH
6-CH
3SO
2NHCH
2CH=CH
2H OCH
3OCH
3CH
6-OCH
3SO
2NHCH
2CH=CH
2H OCH
3OCH
3CH
6-F SO
2NHCH
2CH=CH
2H OCH
3OCH
3CH
6-Cl SO
2NHCH
2CH=CH
2H OCH
3OCH
3CH
H SO
2NHCH
2C≡CH H OCH
3OCH
3CH
H SO
2NHCH
2C≡CH H OCH
3CH
3CH
H SO
2NHCH
2C≡CH H Cl OCH
3CH
H SO
2NHCH
2C≡CH H CH
3CH
3CH
H SO
2NHCH
2C≡CH H OCH
3OCH
3N
H SO
2NHCH
2C≡CH H OCH
3CH
3N
H SO
2NHCH
2C≡CH H OCH
2CH
3NHCH
3N
H SO
2NHCH
2C≡CH CH
3OCH
3CH
3N
4-CH
3SO
2NHCH
2C≡CH H OCH
3OCH
3CH
4-OCH
3SO
2NHCH
2C≡CH H OCH
3OCH
3CH
6-CH
3SO
2NHCH
2C≡CH H OCH
3OCH
3CH
6-OCH SO
2NHCH
2C≡CH H OCH
3OCH
3CH
6-F SO
2NHCH
2C≡CH H OCH
3OCH
3CH
6-Cl SO
2NHCH
2C≡CH H OCH
3OCH
3CH
H SO
2NHCH
2OCH
3H OCH
3OCH
3CH
H SO
2NHCH
2OCH
3H OCH
3CH
3CH
H SO
2NHCH
2OCH
3H CL OCH
3CH
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
H SO
2NHCH
2OCH
3H CH
3CH
3CH
H SO
2NHCH
2OCH
3H OCH
3OCH
3N
H SO
2NHCH
2OCH
3H OCH
3CH
3N
H SO
2NHCH
2OCH
3H OCH
2CH
3NHCH
3N
H SO
2NHCH
2OCH
3CH
3OCH
3CH
3N
4-CH
3SO
2NHCH
2OCH
3H OCH
3OCH
3CH
4-OCH
3SO
2NHCH
2OCH
3H OCH
3OCH
3CH
6-CH
3SO
2NHCH
2OCH
3H OCH
3OCH
3CH
6-OCH
3SO
2NHCH
2OCH
3H OCH
3OCH
3CH
6-F SO
2NHCH
2OCH
3H OCH
3OCH
3CH
6-Cl SO
2NHCH
2OCH
3H OCH
3OCH
3CH
H SO
2NHCH
2CF
3H OCH
3OCH
3CH
H SO
2NHCH
2CF
3H OCH
3CH
3CH
H SO
2NHCH
2CF
3H Cl OCH
3CH
H SO
2NHCH
2CF
3H CH
3CH
3CH
H SO
2NHCH
2CF
3H OCH
3OCH
3N
H SO
2NHCH
2CF
3H OCH
3CH
3N
H SO
2NHCH
2CF
3H OCH
2CH
3NHCH
3N
H SO
2NHCH
2CF
3CH
3OCH
3CH
3N
4-CH
3SO
2NHCH
2CF
3H OCH
3OCH
3CH
4-OCH
3SO
2NHCH
2CF
3H OCH
3OCH
3CH
6-CH
3SO
2NHCH
2CF
3H OCH
3OCH
3CH
6-OCH SO
2NHCH
2CF
3H OCH
3OCH
3CH
6-F SO
2NHCH
2CF
3H OCH
3OCH
3CH
6-Cl SO
2NHCH
2CN H OCH
3OCH
3CH
H SO
2NHCH
2CN H OCH
3OCH
3CH
H SO
2NHCH
2CN H OCH
3CH
3CH
H SO
2NHCH
2CN H CL OCH
3CH
H SO
2NHCH
2CN H CH
3CH
3CH
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
H SO
2NHCH
2CN H OCH
3OCH
3N
H SO
2NHCH
2CN H OCH
3CH
3N
H SO
2NHCH
2CN H OCH
2CH
3NHCH
3N
H SO
2NHCH
2CN CH
3OCH
3CH
3N
4-CH
3SO
2NHCH
2CN H OCH
3OCH
3CH
4-OCH
3SO
2NHCH
2CN H OCH
3OCH
3CH
6-CH
3SO
2NHCH
2CN H OCH
3OCH
3CH
6-OCH
3SO
2NHCH
2CN H OCH
3OCH
3CH
6-F SO
2NHCH
2CN H OCH
3OCH
3CH
6-Cl SO
2NHCH
2CN H OCH
3OCH
3CH
H SO
2N(CH
2CH=CH
2)
2H OCH
3OCH
3CH
H SO
2N(CH
2CH=CH
2)
2H OCH
3CH
3CH
H SO
2N(CH
2CH=CH
2)
2H Cl OCH
3CH
H SO
2N(CH
2CH=CH
2)
2H CH
3CH
3CH
H SO
2N(CH
2CH=CH
2)
2H OCH
3OCH
3N
H SO
2N(CH
2CH=CH
2)
2H OCH
3CH
3N
H SO
2N(CH
2CH=CH
2)
2H OCH
2CH
3NHCH
3N
H SO
2N(CH
2CH=CH
2)
2CH
3OCH
3CH
3N
4-CH
3SO
2N(CH
2CH=CH
2)
2H OCH
3OCH
3CH
4-OCH
3SO
2N(CH
2CH=CH
2)
2H OCH
3OCH
3CH
6-CH
3SO
2N(CH
2CH=CH
2)
2H OCH
3OCH
3CH
6-OCH
3SO
2N(CH
2CH=CH
2)
2H OCH
3OCH
3CH
6-F SO
2N(CH
2CH=CH
2)
2H OCH
3OCH
3CH
6-Cl SO
2-pyrrolidyl H OCH
3OCH
3CH
H SO
2-pyrrolidyl H OCH
3OCH
3CH
H SO
2-pyrrolidyl H OCH
3CH
3CH
H SO
2-pyrrolidyl H CL OCH
3CH
H SO
2-pyrrolidyl H CH
3CH
3CH
H SO
2-pyrrolidyl H OCH
3OCH
3N
H SO
2-pyrrolidyl H OCH
3CH
3N
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
H SO
2-pyrrolidyl H OCH
2CH
3NHCH
3N
H SO
2-pyrrolidyl CH
3OCH
3CH
3N
4-CH
3SO
2-pyrrolidyl H OCH
3OCH
3CH
4-OCH
3SO
2-pyrrolidyl H OCH
3OCH
3CH
6-CH
3SO
2-pyrrolidyl H OCH
3OCH
3CH
6-OCH
3SO
2-pyrrolidyl H OCH
3OCH
3CH
6-F SO
2-pyrrolidyl H OCH
3OCH
3CH
6-Cl SO
2-pyrrolidyl H OCH
3OCH
3CH
H SO
2NHCH
2CH
2OCH
3H OCH
3OCH
3CH
H SO
2NHCH
2CH
2OCH
3H OCH
3CH
3CH
H SO
2NHCH
2CH
2OCH
3H Cl OCH
3CH
H SO
2NHCH
2CH
2OCH
3H CH
3CH
3CH
H SO
2NHCH
2CH
2OCH
3H OCH
3OCH
3N
H SO
2NHCH
2CH
2OCH
3H OCH
3CH
3N
H SO
2NHCH
2CH
2OCH
3H OCH
2CH
3NHCH
3N
H SO
2NHCH
2CH
2OCH
3CH
3OCH
3CH
3N
4-CH
3SO
2NHCH
2CH
2OCH
3H OCH
3OCH
3CH
4-OCH
3SO
2NHCH
2CH
2OCH
3H OCH
3OCH
3CH
6-CH
3SO
2NHCH
2CH
2OCH
3H OCH
3OCH
3CH
6-OCH
3SO
2NHCH
2CH
2OCH
3H OCH
3OCH
3CH
6-F SO
2NHCH
2CH
2OCH
3H OCH
3OCH
3CH
6-Cl SO
2NHCH
2CH
2OCH
3H OCH
3OCH
3CH
H SO
2-pyrrolidyl H OCH
3OCH
3CH 146-149
H SO
2-pyrrolidyl H CH
3CH
3CH 169-171
6-CH
2CH
3CO
2CH
3H OCH
3OCH
3CH
6-CH
2CH
3CO
2CH
3H OCH
3CH
3CH
6-CH
2CH
3CO
2CH
3H Cl OCH
3CH
6-CH
2CH
3CO
2CH
3H CH
3CH
3CH
6-CH
2CH
3CO
2CH
3H OCH
3OCH
3N
6-CH
2CH
3CO
2CH
3H OCH
3CH
3N
6-CH
2CH
3CO
2CH
3H OCH
2CH
3NHCH
3N
6-CH
2CH
3CO
2CH
3CH
3OCH
3CH
3N
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
6-OCH
3CO
2CH
3H OCH
3OCH
3CH 194-196
6-OCH
3CO
2CH
3H OCH
3CH
3CH 165-167
6-OCH
3CO
2CH
3H Cl OCH
3CH 173-175
6-OCH
3CO
2CH
3H CH
3CH
3CH 138.5-145
6-OCH
3CO
2CH
3H OCH
3OCH
3N 173-176
6-OCH
3CO
2CH
3H OCH
3CH
3N 158-161
6-OCH
3CO
2CH
3H OCH
2CH
3NHCH
3N
6-OCH
3CO
2CH
3CH
3OCH
3CH
3N
6-OCH
2CH
3CO
2CH
3H OCH
3OCH
3CH 154-157
6-OCH
2CH
3CO
2CH
3H OCH
3CH
3CH 160-162
6-OCH
2CH
3CO
2CH
3H Cl OCH
3CH 130-132
6-OCH
2CH
3CO
2CH
3H CH
3CH
3CH 140-141
6-OCH
2CH
3CO
2CH
3H OCH
3OCH
3N 160-162
6-OCH
2CH
3CO
2CH
3H OCH
3CH
3N 152-153
6-OCH
2CH
3CO
2CH
3H OCH
2CH
3NHCH
3N
6-OCH
2CH
3CO
2CH
3CH
3OCH
3CH
3N
6-OCF
3CO
2CH
3H OCH
3OCH
3CH
6-OCF
3CO
2CH
3H OCH
3CH
3CH
6-OCF
3CO
2CH
3H Cl OCH
3CH
6-OCF
3CO
2CH
3H CH
3CH
3CH
6-OCF
3CO
2CH
3H OCH
3OCH
3N
6-OCF
3CO
2CH
3H OCH
3CH
3N
6-OCH
2CF
3CO
2CH
3H OCH
3OCH
3CH 158-162
6-OCH
2CF
3CO
2CH
3H OCH
3CH
3CH 168-170
6-OCH
2CF
3CO
2CH
3H Cl OCH
3CH 149-150
6-OCH
2CF
3CO
2CH
3H CH
3CH
3CH 150-152
6-OCH
2CF
3CO
2CH
3H OCH
3OCH
3N
6-OCH
2CF
3CO
2CH
3H OCH
3CH
3N
6-OCH
2CF
3CO
2CH
3H OCH
2CH
3NHCH
3N
6-OCH
2CF
3CO
2CH
3CH
3OCH
3CH
3N
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
6-OCF
3CO
2CH
3H OCH
2CH
3NHCH
3N
6-OCF
3CO
2CH
3CH
3OCH
3CH
3N
6-OCF
2H CO
2CH
3H OCH
3OCH
3CH
6-OCF
2H CO
2CH
3H OCH
3CH
3CH
6-OCF
2H CO
2CH
3H Cl OCH
3CH
6-OCF
2H CO
2CH
3H CH
3CH
3CH
6-OCF
2H CO
2CH
3H OCH
3OCH
3N
6-OCF
2H CO
2CH
3H OCH
3CH
3N
6-OCF
2H CO
2CH
3H OCH
2CH
3NHCH
3N
6-OCF
2H CO
2CH
3CH
3OCH
3CH
3N
6-SCH
3CO
2CH
3H OCH
3OCH
3CH
6-SCH
3CO
2CH
3H OCH
3CH
3CH
6-SCH
3CO
2CH
3H Cl OCH
3CH
6-SCH
3CO
2CH
3H CH
3CH
3CH
6-SCH
3CO
2CH
3H OCH
3OCH
3N
6-SCH
3CO
2CH
3H OCH
3CH
3N
6-SCH
3CO
2CH
3H OCH
2CH
3NHCH
3N
6-SCH
3CO
2CH
3CH
3OCH
3CH
3N
6-SCH
2CH
3CO
2CH
3H OCH
3OCH
3CH
6-SCH
2CH
3CO
2CH
3H OCH
3CH
3CH
6-SCH
2CH
3CO
2CH
3H Cl OCH
3CH
6-SCH
2CH
3CO
2CH
3H CH
3CH
3CH
6-SCH
2CH
3CO
2CH
3H OCH
3OCH
3N
6-SCH
2CH
3CO
2CH
3H OCH
3CH
3N
6-SCH
2CH
3CO
2CH
3H OCH
2CH
3NHCH
3N
6-SCH
2CH
3CO
2CH
3CH
3OCH
3CH
3N
6-N(CH
3)
2CO
2CH
3H OCH
3OCH
3CH 164-167
6-N(CH
3)
2CO
2CH
3H OCH
3CH
3CH 178-179
6-N(CH
3)
2CO
2CH
3H Cl OCH
3CH 147-150
6-N(CH
3)
2CO
2CH
3H CH
3CH
3CH 164-165
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
6-N(CH
3)
2CO
2CH
3H OCH
3OCH
3N 171-172
6-N(CH
3)
2CO
2CH
3H OCH
3CH
3N 132-134
6-N(CH
3)
2CO
2CH
3H OCH
2CH
3NHCH
3N 152-155
6-N(CH
3)
2CO
2CH
3CH
3OCH
3CH
3N
6-NHCH
3CO
2CH
3H OCH
3OCH
3CH
6-NHCH
3CO
2CH
3H OCH
3CH
3CH
6-NHCH
3CO
2CH
3H Cl OCH
3CH
6-NHCH
3CO
2CH
3H CH
3CH
3CH
6-NHCH
3CO
2CH
3H OCH
3OCH
3N
6-NHCH
3CO
2CH
3H OCH
3CH
3N
6-NHCH
3CO
2CH
3H OCH
2CH
3NHCH
3N
6-NHCH
3CO
2CH
3CH
3OCH
3CH
3N
6-CH
2CH
3CO
2CH
2CH
3H OCH
3OCH
3CH
6-CH
2CH
3CO
2CH
2CH
3H OCH
3CH
3CH
6-CH
2CH
3CO
2CH
2CH
3H Cl OCH
3CH
6-CH
2CH
3CO
2CH
2CH
3H CH
3CH
3CH
6-CH
2CH
3CO
2CH
2CH
3H OCH
3OCH
3N
6-CH
2CH
3CO
2CH
2CH
3H OCH
3CH
3N
6-CH
2CH
3CO
2CH
2CH
3H OCH
2CH
3NHCH
3N
6-CH
2CH
3CO
2CH
2CH
3CH
3OCH
3CH
3N
6-OCH
3CO
2CH
2CH
3H OCH
3OCH
3CH 158-161
6-OCH
3CO
2CH
2CH
3H OCH
3CH
3CH 147-149
6-OCH
3CO
2CH
2CH
3H Cl OCH
3CH 124-127
6-OCH
3CO
2CH
2CH
3H CH
3CH
3CH 149-151
6-OCH
3CO
2CH
2CH
3H OCH
3OCH
3N 164-165
6-OCH
3CO
2CH
2CH
3H OCH
3CH
3N 131-132
6-OCH
3CO
2CH
2CH
3H OCH
2CH
3NHCH
3N
6-OCH
3CO
2CH
2CH
3CH
3OCH
3CH
3N
6-OCH
2CH
3CO
2CH
2CH
3H OCH
3OCH
3CH 152-154
6-OCH
2CH
3CO
2CH
2CH
3H OCH
3CH
3CH 134-135
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
6-OCH
2CH
3CO
2CH
2CH
3H Cl OCH
3CH 153-160
6-OCH
2CH
3CO
2CH
2CH
3H CH
3CH
3CH 159-163
6-OCH
2CH
3CO
2CH
2CH
3H OCH
3OCH
3N 320-330
6-OCH
2CH
3CO
2CH
2CH
3H OCH
3CH
3N
6-OCH
2CH
3CO
2CH
2CH
3H OCH
2CH
3NHCH
3N
6-OCH
2CH
3CO
2CH
2CH
3CH
3OCH
3CH
3N
6-OCH
2CF
3CO
2CH
2CH
3H OCH
3OCH
3CH 173-175
6-OCH
2CF
3CO
2CH
2CH
3H OCH
3CH
3CH 166-167
6-OCH
2CF
3CO
2CH
2CH
3H Cl OCH
3CH 150-152
6-OCH
2CF
3CO
2CH
2CH
3H CH
3CH
3CH 142-144
6-OCH
2CF
3CO
2CH
2CH
3H OCH
3OCH
3N 138-141
6-OCH
2CF
3CO
2CH
2CH
3H OCH
3CH
3N 122-126
6-OCH
2CF
3CO
2CH
2CH
3H OCH
2CH
3NHCH
3N
6-OCH
2CF
3CO
2CH
2CH
3CH
3OCH
3CH
3N
6-OCF
3CO
2CH
2CH
3H OCH
3OCH
3CH
6-OCF
3CO
2CH
2CH
3H OCH
3CH
3CH
6-OCF
3CO
2CH
2CH
3H Cl OCH
3CH
6-OCF
3CO
2CH
2CH
3H CH
3CH
3CH
6-OCF
3CO
2CH
2CH
3H OCH
3OCH
3N
6-OCF
3CO
2CH
2CH
3H OCH
3CH
3N
6-OCF
3CO
2CH
2CH
3H OCH
2CH
3NHCH
3N
6-OCF
3CO
2CH
2CH
3CH
3OCH
3CH
3N
6-OCF
2H CO
2CH
2CH
3H OCH
3OCH
3CH
6-OCF
2H CO
2CH
2CH
3H OCH
3CH
3CH
6-OCF
2H CO
2CH
2CH
3H Cl OCH
3CH
6-OCF
2H CO
2CH
2CH
3H CH
3CH
3CH
6-OCF
2H CO
2CH
2CH
3H OCH
3OCH
3N
6-OCF
2H CO
2CH
2CH
3H OCH
3CH
3N
6-OCF
2H CO
2CH
2CH
3H OCH
2CH
3NHCH
3N
6-OCF
2H CO
2CH
2CH
3CH
3OCH
3CH
3N
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
6-SCH
3CO
2CH
2CH
3H OCH
3OCH
3CH
6-SCH
3CO
2CH
2CH
3H OCH
3CH
3CH
6-SCH
3CO
2CH
2CH
3H Cl OCH
3CH
6-SCH
3CO
2CH
2CH
3H CH
3CH
3CH
6-SCH
3CO
2CH
2CH
3H OCH
3OCH
3N
6-SCH
3CO
2CH
2CH
3H OCH
3CH
3N
6-SCH
3CO
2CH
2CH
3H OCH
2CH
3NHCH
3N
6-SCH
3CO
2CH
2CH
3CH
3OCH
3CH
3N
6-SCH
2CH
3CO
2CH
2CH
3H OCH
3OCH
3CH
6-SCH
2CH
3CO
2CH
2CH
3H OCH
3CH
3CH
6-SCH
2CH
3CO
2CH
2CH
3H Cl OCH
3CH
6-SCH
2CH
3CO
2CH
2CH
3H CH
3CH
3CH
6-SCH
2CH
3CO
2CH
2CH
3H OCH
3OCH
3N
6-SCH
2CH
3CO
2CH
2CH
3H OCH
3CH
3N
6-SCH
2CH
3CO
2CH
2CH
3H OCH
2CH
3NHCH
3N
6-SCH
2CH
3CO
2CH
2CH
3CH
3OCH
3CH
3N
6-N(CH
3)
2CO
2CH
2CH
3H OCH
3OCH
3CH 147-149
6-N(CH
3)
2CO
2CH
2CH
3H OCH
3CH
3CH 149-150
6-N(CH
3)
2CO
2CH
2CH
3H Cl OCH
3CH 150-151
6-N(CH
3)
2CO
2CH
2CH
3H CH
3CH
3CH 172-175
6-N(CH
3)
2CO
2CH
2CH
3H OCH
3OCH
3N 152-153
6-N(CH
3)
2CO
2CH
2CH
3H OCH
3CH
3N 148-150
6-N(CH
3)
2CO
2CH
2CH
3H OCH
2CH
3NHCH
3N
6-N(CH
3)
2CO
2CH
2CH
3CH
3OCH
3CH
3N
6-NHCH
3CO
2CH
2CH
3H OCH
3OCH
3CH
6-NHCH
3CO
2CH
2CH
3H OCH
3CH
3CH
6-NHCH
3CO
2CH
2CH
3H Cl OCH
3CH
6-NHCH
3CO
2CH
2CH
3H CH
3CH
3CH
6-NHCH
3CO
2CH
2CH
3H OCH
3OCH
3N
6-NHCH
3CO
2CH
2CH
3H OCH
3CH
3N
6-NHCH
3CO
2CH
2CH
3H OCH
2CH
3NHCH
3N
6-NHCH
3CO
2CH
2CH
3CH
3OCH
3CH
3N
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
H CO
2CH
2CH
2OH H OCH
3OCH
3CH
H CO
2CH
2CH
2OH H OCH
3CH
3CH
H CO
2CH
2CH
2OH H Cl OCH
3CH
H CO
2CH
2CH
2OH H CH
3CH
3CH
H CO
2CH
2CH
2OH H OCH
3OCH
3N
H CO
2CH
2CH
2OH H OCH
3CH
3N
H CO
2CH
2CH
2OH H OCH
2CH
3NHCH
3N
H CO
2CH
2CH
2OH CH
3OCH
3CH
3N
4-CH
3CO
2CH
2CH
2OH H OCH
3OCH
3CH
4-OCH
3CO
2CH
2CH
2OH H OCH
3OCH
3CH
6-CH
3CO
2CH
2CH
2OH H OCH
3OCH
3CH
6-OCH
3CO
2CH
2CH
2OH H OCH
3OCH
3CH
6-F CO
2CH
2CH
2OH H OCH
3OCH
3CH
6-Cl CO
2CH
2CH
2OH H OCH
3OCH
3CH
H CO
2CH
2CH
2CN H OCH
3OCH
3CH
H CO
2CH
2CH
2CN H OCH
3CH
3CH
H CO
2CH
2CH
2CN H Cl OCH
3CH
H CO
2CH
2CH
2CN H CH
3CH
3CH
H CO
2CH
2CH
2CN H OCH
3OCH
3N
H CO
2CH
2CH
2CN H OCH
3CH
3N
H CO
2CH
2CH
2CN H OCH
2CH
3NHCH
3N
H CO
2CH
2CH
2CN CH
3OCH
3CH
3N
4-CH
3CO
2CH
2CH
2CN H OCH
3OCH
3CH
4-OCH
3CO
2CH
2CH
2CN H OCH
3OCH
3CH
6-CH
3CO
2CH
2CH
2CN H OCH
3OCH
3CH
6-OCH
3CO
2CH
2CH
2CN H OCH
3OCH
3CH
6-F CO
2CH
2CH
2CN H OCH
3OCH
3CH
6-Cl CO
2CH
2CH
2CN H OCH
3OCH
3CH
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
H CO
2CH
2CH
2OSO
2CH
3H OCH
3OCH
3CH
H CO
2CH
2CH
2OSO
2CH
3H OCH
3CH
3CH
H CO
2CH
2CH
2OSO
2CH
3H Cl OCH
3CH
H CO
2CH
2CH
2OSO
2CH
3H CH
3CH
3CH
H CO
2CH
2CH
2OSO
2CH
3H OCH
3OCH
3N
H CO
2CH
2CH
2OSO
2CH
3H OCH
3CH
3N
H CO
2CH
2CH
2OSO
2CH
3H OCH
2CH
3NHCH
3N
H CO
2CH
2CH
2OSO
2CH
3CH
3OCH
3CH
3N
4-CH
3CO
2CH
2CH
2OSO
2CH
3H OCH
3OCH
3CH
4-OCH
3CO
2CH
2CH
2OSO
2CH
3H OCH
3OCH
3CH
6-CH
3CO
2CH
2CH
2OSO
2CH
3H OCH
3OCH
3CH
6-OCH
3CO
2CH
2CH
2OSO
2CH
3H OCH
3OCH
3CH
6-F CO
2CH
2CH
2OSO
2CH
3H OCH
3OCH
3CH
6-Cl CO
2CH
2CH
2OSO
2CH
3H OCH
3OCH
3CH
H CO
2CH
2CH
2OSO
2CF
3H OCH
3OCH
3CH
H CO
2CH
2CH
2OSO
2CF
3H OCH
3CH
3CH
H CO
2CH
2CH
2OSO
2CF
3H Cl OCH
3CH
H CO
2CH
2CH
2OSO
2CF
3H CH
3CH
3CH
H CO
2CH
2CH
2OSO
2CF
3H OCH
3OCH
3N
H CO
2CH
2CH
2OSO
2CF
3H OCH
3CH
3N
H CO
2CH
2CH
2OSO
2CF
3H OCH
2CH
3NHCH
3N
H CO
2CH
2CH
2OSO
2CF
3CH
3OCH
3CH
3N
4-CH
3CO
2CH
2CH
2OSO
2CF
3H OCH
3OCH
3CH
4-OCH
3CO
2CH
2CH
2OSO
2CF
3H OCH
3OCH
3CH
6-CH
3CO
2CH
2CH
2OSO
2CF
3H OCH
3OCH
3CH
6-OCH
3CO
2CH
2CH
2OSO
2CF
3H OCH
3OCH
3CH
6-F CO
2CH
2CH
2OSO
2CF
3H OCH
3OCH
3CH
6-Cl CO
2CH
2CH
2OSO
2CF
3H OCH
3OCH
3CH
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
H CO
2CH
2CF
3H OCH
3OCH
3CH
H CO
2CH
2CF
3H OCH
3CH
3CH
H CO
2CH
2CF
3H Cl OCH
3CH
H CO
2CH
2CF
3H CH
3CH
3CH
H CO
2CH
2CF
3H OCH
3OCH
3N
H CO
2CH
2CF
3H OCH
3CH
3N
H CO
2CH
2CF
3H OCH
2CH
3NHCH
3N
H CO
2CH
2CF
3CH
3OCH
3CH
3N
4-CH
3CO
2CH
2CF
3H OCH
3OCH
3CH
4-OCH
3CO
2CH
2CF
3H OCH
3OCH
3CH
6-CH
3CO
2CH
2CF
3H OCH
3OCH
3CH
6-OCH
3CO
2CH
2CF
3H OCH
3OCH
3CH
6-F CO
2CH
2CF
3H OCH
3OCH
3CH
6-Cl CO
2CH
2CF
3H OCH
3OCH
3CH
H CO
2CH
2C≡CH H OCH
3OCH
3CH 127-128
H CO
2CH
2C≡CH H OCH
3CH
3CH 142-144
H CO
2CH
2C≡CH H Cl OCH
3CH 154-156
H CO
2CH
2C≡CH H CH
3CH
3CH 141-142
H CO
2CH
2C≡CH H OCH
3OCH
3N 137-138
H CO
2CH
2C≡CH H OCH
3CH
3N 136-137
H CO
2CH
2C≡CH H OCH
2CH
3NHCH
3N
H CO
2CH
2C≡CH CH
3OCH
3CH
3N
4-CH
3CO
2CH
2C≡CH H OCH
3OCH
3CH
4-OCH
3CO
2CH
2C≡CH H OCH
3OCH
3CH
6-CH
3CO
2CH
2C≡CH H OCH
3OCH
3CH
6-OCH
3CO
2CH
2C≡CH H OCH
3OCH
3CH
6-F CO
2CH
2C≡CH H OCH
3OCH
3CH
6-Cl CO
2CH
2C≡CH H OCH
3OCH
3CH
Table I (continuing)
R
1R
2R X Y Z m.p.(℃)
H CO
2CH
2CH
2CH
2Cl H OCH
3OCH
3CH
H CO
2CH
2CH
2CH
2Cl H OCH
3CH
3CH
H CO
2CH
2CH
2CH
2Cl H Cl OCH
3CH
H CO
2CH
2CH
2CH
2Cl H CH
3CH
3CH
H CO
2CH
2CH
2CH
2Cl H OCH
3OCH
3N
H CO
2CH
2CH
2CH
2Cl H OCH
3CH
3N
H CO
2CH
2CH
2CH
2Cl H OCH
2CH
3NHCH
3N
H CO
2CH
2CH
2CH
2Cl CH
3OCH
3CH
3N
4-CH
3CO
2CH
2CH
2CH
2Cl H OCH
3OCH
3CH
4-OCH
3CO
2CH
2CH
2CH
2Cl H OCH
3OCH
3CH
6-CH
3CO
2CH
2CH
2CH
2Cl H OCH
3OCH
3CH
6-OCH
3CO
2CH
2CH
2CH
2Cl H OCH
3OCH
3CH
6-F CO
2CH
2CH
2CH
2Cl H OCH
3OCH
3CH
6-Cl CO
2CH
2CH
2CH
2Cl H OCH
3OCH
3CH
H CO
2CH
2CH
2SCH
3H OCH
3OCH
3CH
H CO
2CH
2CH
2SCH
3H OCH
3CH
3CH
H CO
2CH
2CH
2SCH
3H Cl OCH
3CH
H CO
2CH
2CH
2SCH
3H CH
3CH
3CH
H CO
2CH
2CH
2SCH
3H OCH
3OCH
3N
H CO
2CH
2CH
2SCH
3H OCH
3CH
3N
H CO
2CH
2CH
2SCH
3H OCH
2CH
3NHCH
3N
H CO
2CH
2CH
2SCH
3CH
3OCH
3CH
3N
4-CH
3CO
2CH
2CH
2SCH
3H OCH
3OCH
3CH
4-OCH
3CO
2CH
2CH
2SCH
3H OCH
3OCH
3CH
6-CH
3CO
2CH
2CH
2SCH
3H OCH
3OCH
3CH
6-OCH
3CO
2CH
2CH
2SCH
3H OCH
3OCH
3CH
6-F CO
2CH
2CH
2SCH
3H OCH
3OCH
3CH
6-Cl CO
2CH
2CH
2SCH
3H OCH
3OCH
3CH
H CO
2CH
2-cyclopropyl H OCH
3OCH
3CH 143-145
H CO
2CH
2-cyclopropyl H Cl OCH
3CH 124-128
H CO
2CH
2-cyclopropyl H CH
3CH
3CH 134-138
H CO
2CH
2-cyclopropyl H OCH
3OCH
3N 154-161
The table II
General formula 2
R
1R
3R X Y Z m.p.(℃)
H SOCH
3H OCH
3OCH
3CH
H SOCH
3H OCH
3CH
3CH
H SOCH
3H Cl OCH
3CH
H SOCH
3H CH
3CH
3CH
H SOCH
3H OCH
3OCH
3N
H SOCH
3H OCH
3CH
3N
H SOCH
3CH
3OCH
3CH
3N
4-CH
3SOCH
3H OCH
3OCH
3CH
4-Cl SOCH
3H OCH
3OCH
3CH
6-CH
3SOCH
3H OCH
3OCH
3CH
6-OCH
3SOCH
3H OCH
3OCH
3CH
6-F SOCH
3H OCH
3OCH
3CH
6-Cl SOCH
3H OCH
3OCH
3CH
H SOCH
2CH
3H OCH
3OCH
3CH
H SOCH
2CH
3H OCH
3CH
3CH
H SOCH
2CH
3H Cl OCH
3CH
H SOCH
2CH
3H CH
3CH
3CH
H SOCH
2CH
3H OCH
3OCH
3N
H SOCH
2CH
3H OCH
3CH
3N
H SOCH
2CH
3CH
3OCH
3CH
3N
4-CH
3SOCH
2CH
3H OCH
3OCH
3CH
4-Cl SOCH
2CH
3H OCH
3OCH
3CH
6-CH
3SOCH
2CH
3H OCH
3OCH
3CH
6-OCH
3SOCH
2CH
3H OCH
3OCH
3CH
6-F SOCH
2CH
3H OCH
3OCH
3CH
6-Cl SOCH
2CH
3H OCH
3OCH
3CH
Table II (continuing)
R
1R
3R X Y Z m.p.(℃)
H SOCH
2CH
2CH
3H OCH
3OCH
3CH
H SOCH
2CH
2CH
3H OCH
3CH
3CH
H SOCH
2CH
2CH
3H Cl OCH
3CH
H SOCH
2CH
2CH
3H CH
3CH
3CH
H SOCH
2CH
2CH
3H OCH
3OCH
3N
H SOCH
2CH
2CH
3H OCH
3CH
3N
H SOCH
2CH
2CH
3CH
3OCH
3CH
3N
4-CH
3SOCH
2CH
2CH
3H OCH
3OCH
3CH
4-Cl SOCH
2CH
2CH
3H OCH
3OCH
3CH
6-CH
3SOCH
2CH
2CH
3H OCH
3OCH
3CH
6-OCH
3SOCH
2CH
2CH
3H OCH
3OCH
3CH
6-F SOCH
2CH
2CH
3H OCH
3OCH
3CH
6-Cl SOCH
2CH
2CH
3H OCH
3OCH
3CH
H SOCH
2CH
2CH
2CH
3H OCH
3OCH
3CH
H SOCH
2CH
2CH
2CH
3H OCH
3CH
3CH
H SOCH
2CH
2CH
2CH
3H Cl OCH
3CH
H SOCH
2CH
2CH
2CH
3H CH
3CH
3CH
H SOCH
2CH
2CH
2CH
3H OCH
3OCH
3N
H SOCH
2CH
2CH
2CH
3H OCH
3CH
3N
H SOCH
2CH
2CH
2CH
3CH
3OCH
3CH
3N
4-CH
3SOCH
2CH
2CH
2CH
3H OCH
3OCH
3CH
4-Cl SOCH
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-CH
3SOCH
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-OCH
3SOCH
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-F SOCH
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-Cl SOCH
2CH
2CH
2CH
3H OCH
3OCH
3CH
Table II (continuing)
R
1R
3R X Y Z m.p.(℃)
H SOCH(CH
3)
2H OCH
3OCH
3CH
H SOCH(CH
3)
2H OCH
3CH
3CH
H SOCH(CH
3)
2H Cl OCH
3CH
H SOCH(CH
3)
2H CH
3CH
3CH
H SOCH(CH
3)
2H OCH
3OCH
3N
H SOCH(CH
3)
2H OCH
3CH
3N
H SOCH(CH
3)
2CH
3OCH
3CH
3N
4-CH
3SOCH(CH
3)
2H OCH
3OCH
3CH
4-Cl SOCH(CH
3)
2H OCH
3OCH
3CH
6-CH
3SOCH(CH
3)
2H OCH
3OCH
3CH
6-OCH
3SOCH(CH
3)
2H OCH
3OCH
3CH
6-F SOCH(CH
3)
2H OCH
3OCH
3CH
6-Cl SOCH(CH
3)
2H OCH
3OCH
3CH
H S-cyclopropyl H OCH
3OCH
3CH
H S-cyclopropyl H OCH
3CH
3CH
H S-cyclopropyl H Cl OCH
3CH
H S-cyclopropyl H CH
3CH
3CH
H S-cyclopropyl H OCH
3OCH
3N
H S-cyclopropyl H OCH
3CH
3N
H S-cyclopropyl H OCH
2CH
3NHCH
3N
H S-cyclopropyl CH
3OCH
3CH
3N
4-CH
3S-cyclopropyl H OCH
3OCH
3CH
4-Cl S-cyclopropyl H OCH
3OCH
3CH
6-CH
3S-cyclopropyl H OCH
3OCH
3CH
6-OCH
3S-cyclopropyl H OCH
3OCH
3CH
6-F S-cyclopropyl H OCH
3OCH
3CH
6-Cl S-cyclopropyl H OCH
3OCH
3CH
Table II (continuing)
R
1R
3R X Y Z m.p.(℃)
H SO-cyclopropyl H OCH
3OCH
3CH
H SO-cyclopropyl H OCH
3CH
3CH
H SO-cyclopropyl H Cl OCH
3CH
H SO-cyclopropyl H CH
3CH
3CH
H SO-cyclopropyl H OCH
3OCH
3N
H SO-cyclopropyl H OCH
3CH
3N
H SO-cyclopropyl H OCH
2CH
3NHCH
3N
H SO-cyclopropyl CH
3OCH
3CH
3N
4-CH
3SO-cyclopropyl H OCH
3OCH
3CH
4-Cl SO-cyclopropyl H OCH
3OCH
3CH
6-CH
3SO-cyclopropyl H OCH
3OCH
3CH
6-OCH
3SO-cyclopropyl H OCH
3OCH
3CH
6-F SO-cyclopropyl H OCH
3OCH
3CH
6-Cl SO-cyclopropyl H OCH
3OCH
3CH
H SO
2-cyclopropyl H OCH
3OCH
3CH
H SO
2-cyclopropyl H OCH
3CH
3CH
H SO
2-cyclopropyl H Cl OCH
3CH
H SO
2-cyclopropyl H CH
3CH
3CH
H SO
2-cyclopropyl H OCH
3OCH
3N
H SO
2-cyclopropyl H OCH
3CH
3N
H SO
2-cyclopropyl H OCH
2CH
3NHCH
3N
H SO
2-cyclopropyl CH
3OCH
3CH
3N
4-CH
3SO
2-cyclopropyl H OCH
3OCH
3CH
4-Cl SO
2-cyclopropyl H OCH
3OCH
3CH
6-CH
3SO
2-cyclopropyl H OCH
3OCH
3CH
6-OCH
3SO
2-cyclopropyl H OCH
3OCH
3CH
6-F SO
2-cyclopropyl H OCH
3OCH
3CH
6-Cl SO
2-cyclopropyl H OCH
3OCH
3CH
Table II (continuing)
R
1R
3R X Y Z m.p.(℃)
H OSO
2CH
3H OCH
3OCH
3CH
H OSO
2CH
3H OCH
3CH
3CH
H OSO
2CH
3H Cl OCH
3CH
H OSO
2CH
3H CH
3CH
3CH
H OSO
2CH
3H OCH
3OCH
3N
H OSO
2CH
3H OCH
3CH
3N
H OSO
2CH
3H OCH
2CH
3NHCH
3N
H OSO
2CH
3CH
3OCH
3CH
3N
4-CH
3OSO
2CH
3H OCH
3OCH
3CH
4-Cl OSO
2CH
3H OCH
3OCH
3CH
6-CH
3OSO
2CH
3H OCH
3OCH
3CH
6-OCH
3OSO
2CH
3H OCH
3OCH
3CH
6-F OSO
2CH
3H OCH
3OCH
3CH
6-Cl OSO
2CH
3H OCH
3OCH
3CH
H OSO
2CH
2CH
3H OCH
3OCH
3CH
H OSO
2CH
2CH
3H OCH
3CH
3CH
H OSO
2CH
2CH
3H Cl OCH
3CH
H OSO
2CH
2CH
3H CH
3CH
3CH
H OSO
2CH
2CH
3H OCH
3OCH
3N
H OSO
2CH
2CH
3H OCH
3CH
3N
H OSO
2CH
2CH
3H OCH
2CH
3NHCH
3N
H OSO
2CH
2CH
3CH
3OCH
3CH
3N
4-CH
3OSO
2CH
2CH
3H OCH
3OCH
3CH
4-Cl OSO
2CH
2CH
3H OCH
3OCH
3CH
6-CH
3OSO
2CH
2CH
3H OCH
3OCH
3CH
6-OCH
3OSO
2CH
2CH
3H OCH
3OCH
3CH
6-F OSO
2CH
2CH
3H OCH
3OCH
3CH
6-Cl OSO
2CH
2CH
3H OCH
3OCH
3CH
Table II (continuing)
R
1R
3R X Y Z m.p.(℃)
H OSO
2CF
3H OCH
3OCH
3CH
H OSO
2CF
3H OCH
3CH
3CH
H OSO
2CF
3H Cl OCH
3CH
H OSO
2CF
3H CH
3CH
3CH
H OSO
2CF
3H OCH
3OCH
3N
H OSO
2CF
3H OCH
3CH
3N
H OSO
2CF
3H OCH
2CH
3NHCH
3N
H OSO
2CF
3CH
3OCH
3CH
3N
4-CH
3OSO
2CF
3H OCH
3OCH
3CH
4-Cl OSO
2CF
3H OCH
3OCH
3CH
6-CH
3OSO
2CF
3H OCH
3OCH
3CH
6-OCH
3OSO
2CF
3H OCH
3OCH
3CH
6-F OSO
2CF
3H OCH
3OCH
3CH
6-Cl OSO
2CF
3H OCO
3OCH
3CH
H OSO
2CCl
3H OCH
3OCH
3CH
H OSO
2CCl
3H OCH
3CH
3CH
H OSO
2CCl
3H Cl OCH
3CH
H OSO
2CCl
3H CH
3CH
3CH
H OSO
2CCl
3H OCH
3OCH
3N
H OSO
2CCl
3H OCH
3CH
3N
H OSO
2CCl
3H OCH
2CH
3NHCH
3N
H OSO
2CCl
3CH
3OCH
3CH
3N
4-CH
3OSO
2CCl
3H OCH
3OCH
3CH
4-Cl OSO
2CCl
3H OCH
3OCH
3CH
6-CH
3OSO
2CCl
3H OCH
3OCH
3CH
6-OCH
3OSO
2CCl
3H OCH
3OCH
3CH
6-F OSO
2CCl
3H OCH
3OCH
3CH
6-Cl OSO
2CCl
3H OCH
3OCH
3CH
Table II (continuing)
R
1R
3R X Y Z m.p.(℃)
H OSO
2CH
2CH
2CH
3H OCH
3OCH
3CH
H OSO
2CH
2CH
2CH
3H OCH
3CH
3CH
H OSO
2CH
2CH
2CH
3H Cl OCH
3CH
H OSO
2CH
2CH
2CH
3H CH
3CH
3CH
H OSO
2CH
2CH
2CH
3H OCH
3OCH
3N
H OSO
2CH
2CH
2CH
3H OCH
3CH
3N
H OSO
2CH
2CH
2CH
3H OCH
2CH
3NHCH
3N
H OSO
2CH
2CH
2CH
3CH
3OCH
3CH
3N
4-CH
3OSO
2CH
2CH
2CH
3H OCH
3OCH
3CH
4-Cl OSO
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-CH
3OSO
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-OCH
3OSO
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-F OSO
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-Cl OSO
2CH
2CH
2CH
3H OCO
3OCH
3CH
H SO
2OCH
2CF
3H OCH
3OCH
3CH
H SO
2OCH
2CF
3H OCH
3CH
3CH
H SO
2OCH
2CF
3H Cl OCH
3CH
H SO
2OCH
2CF
3H CH
3CH
3CH
H SO
2OCH
2CF
3H OCH
3OCH
3N
H SO
2OCH
2CF
3H OCH
3CH
3N
H SO
2OCH
2CF
3H OCH
2CH
3NHCH
3N
H SO
2OCH
2CF
3CH
3OCH
3CH
3N
4-CH
3SO
2OCH
2CF
3H OCH
3OCH
3CH
4-Cl SO
2OCH
2CF
3H OCH
3OCH
3CH
6-CH
3SO
2OCH
2CF
3H OCH
3OCH
3CH
6-OCH
3SO
2OCH
2CF
3H OCH
3OCH
3CH
6-F SO
2OCH
2CF
3H OCH
3OCH
3CH
6-Cl SO
2OCH
2CF
3H OCH
3OCH
3CH
Table II (continuing)
R
1R
3R X Y Z m.p.(℃)
H P(O)(OCH
3)
2H OCH
3OCH
3CH
H P(O)(OCH
3)
2H OCH
3CH
3CH
H P(O)(OCH
3)
2H Cl OCH
3CH
H P(O)(OCH
3)
2H CH
3CH
3CH
H P(O)(OCH
3)
2H OCH
3OCH
3N
H P(O)(OCH
3)
2H OCH
3CH
3N
H P(O)(OCH
3)
2H OCH
2CH
3NHCH
3N
H P(O)(OCH
3)
2CH
3OCH
3CH
3N
4-CH
3P(O)(OCH
3)
2H OCH
3OCH
3CH
4-Cl P(O)(OCH
3)
2H OCH
3OCH
3CH
6-CH
3P(O)(OCH
3)
2H OCH
3OCH
3CH
6-OCH
3P(O)(OCH
3)
2H OCH
3OCH
3CH
6-F P(O)(OCH
3)
2H OCH
3OCH
3CH
6-Cl P(O)(OCH
3)
2H OCO
3OCH
3CH
H CN H OCH
3OCH
3CH
H CN H OCH
3CH
3CH
H CN H Cl OCH
3CH
H CN H CH
3CH
3CH
H CN H OCH
3OCH
3N
H CN H OCH
3CH
3N
H CN H OCH
2CH
3NHCH
3N
H CN CH
3OCH
3CH
3N
4-CH
3CN H OCH
3OCH
3CH
4-Cl CN H OCH
3OCH
3CH
6-CH
3CN H OCH
3OCH
3CH
6-OCH
3CN H OCH
3OCH
3CH
6-F CN H OCH
3OCH
3CH
6-Cl CN H OCH
3OCH
3CH
Table II (continuing)
R
1R
3R X Y Z m.p.(℃)
H CH
2F H OCH
3OCH
3CH
H CH
2F H OCH
3CH
3CH
H CH
2F H Cl OCH
3CH
H CH
2F H CH
3CH
3CH
H CH
2F H OCH
3OCH
3N
H CH
2F H OCH
3CH
3N
H CH
2F H OCH
2CH
3NHCH
3N
H CH
2F CH
3OCH
3CH
3N
4-CH
3CH
2F H OCH
3OCH
3CH
4-Cl CH
2F H OCH
3OCH
3CH
6-CH
3CH
2F H OCH
3OCH
3CH
6-OCH
3CH
2F H OCH
3OCH
3CH
6-F CH
2F H OCH
3OCH
3CH
6-Cl CH
2F H OCO
3OCH
3CH
H CF
2H H OCH
3OCH
3CH
H CF
2H H OCH
3CH
3CH
H CF
2H H Cl OCH
3CH
H CF
2H H CH
3CH
3CH
H CF
2H H OCH
3OCH
3N
H CF
2H H OCH
3CH
3N
H CF
2H H OCH
2CH
3NHCH
3N
H CF
2H CH
3OCH
3CH
3N
4-CH
3CF
2H H OCH
3OCH
3CH
4-Cl CF
2H H OCH
3OCH
3CH
6-CH
3CF
2H H OCH
3OCH
3CH
6-OCH
3CF
2H H OCH
3OCH
3CH
6-F CF
2H H OCH
3OCH
3CH
6-Cl CF
2H H OCH
3OCH
3CH
Table II (continuing)
R
1R
3R X Y Z m.p.(℃)
H SO
2NHCH
3H OCH
3OCH
3CH
H SO
2NHCH
3H OCH
3CH
3CH
H SO
2NHCH
3H Cl OCH
3CH
H SO
2NHCH
3H CH
3CH
3CH
H SO
2NHCH
3H OCH
3OCH
3N
H SO
2NHCH
3H OCH
3CH
3N
H SO
2NHCH
3H OCH
2CH
3NHCH
3N
H SO
2NHCH
3CH
3OCH
3CH
3N
4-CH
3SO
2NHCH
3H OCH
3OCH
3CH
4-Cl SO
2NHCH
3H OCH
3OCH
3CH
6-CH
3SO
2NHCH
3H OCH
3OCH
3CH
6-OCH
3SO
2NHCH
3H OCH
3OCH
3CH
6-F SO
2NHCH
3H OCH
3OCH
3CH
6-Cl SO
2NHCH
3H OCH
3OCH
3CH
H SO
2NHCH
2CH
3H OCH
3OCH
3CH
H SO
2NHCH
2CH
3H OCH
3CH
3CH
H SO
2NHCH
2CH
3H Cl OCH
3CH
H SO
2NHCH
2CH
3H CH
3CH
3CH
H SO
2NHCH
2CH
3H OCH
3OCH
3N
H SO
2NHCH
2CH
3H OCH
3CH
3N
H SO
2NHCH
2CH
3H OCH
2CH
3NHCH
3N
H SO
2NHCH
2CH
3CH
3OCH
3CH
3N
4-CH
3SO
2NHCH
2CH
3H OCH
3OCH
3CH
4-Cl SO
2NHCH
2CH
3H OCH
3OCH
3CH
6-CH
3SO
2NHCH
2CH
3H OCH
3OCH
3CH
6-OCH
3SO
2NHCH
2CH
3H OCH
3OCH
3CH
6-F SO
2NHCH
2CH
3H OCH
3OCH
3CH
6-Cl SO
2NHCH
2CH
3H OCH
3OCH
3CH
Table II (continuing)
R
1R
3R X Y Z m.p.(℃)
H SO
2NHCH
2CH
2CH
3H OCH
3OCH
3CH
H SO
2NHCH
2CH
2CH
3H OCH
3CH
3CH
H SO
2NHCH
2CH
2CH
3H Cl OCH
3CH
H SO
2NHCH
2CH
2CH
3H CH
3CH
3CH
H SO
2NHCH
2CH
2CH
3H OCH
3OCH
3N
H SO
2NHCH
2CH
2CH
3H OCH
3CH
3N
H SO
2NHCH
2CH
2CH
3H OCH
2CH
3NHCH
3N
H SO
2NHCH
2CH
2CH
3CH
3OCH
3CH
3N
4-CH
3SO
2NHCH
2CH
2CH
3H OCH
3OCH
3CH
4-Cl SO
2NHCH
2CH
2CH
3H OCH
3OCH
3CH
6-CH
3SO
2NHCH
2CH
2CH
3H OCH
3OCH
3CH
6-OCH
3SO
2NHCH
2CH
2CH
3H OCH
3OCH
3CH
6-F SO
2NHCH
2CH
2CH
3H OCH
3OCH
3CH
6-Cl SO
2NHCH
2CH
2CH
3H OCH
3OCH
3CH
H SO
2NHCH(CH
3)
2H OCH
3OCH
3CH
H SO
2NHCH(CH
3)
2H OCH
3CH
3CH
H SO
2NHCH(CH
3)
2H Cl OCH
3CH
H SO
2NHCH(CH
3)
2H CH
3CH
3CH
H SO
2NHCH(CH
3)
2H OCH
3OCH
3N
H SO
2NHCH(CH
3)
2H OCH
3CH
3N
H SO
2NHCH(CH
3)
2H OCH
2CH
3NHCH
3N
H SO
2NHCH(CH
3)
2CH
3OCH
3CH
3N
4-CH
3SO
2NHCH(CH
3)
2H OCH
3OCH
3CH
4-Cl SO
2NHCH(CH
3)
2H OCH
3OCH
3CH
6-CH
3SO
2NHCH(CH
3)
2H OCH
3OCH
3CH
6-OCH
3SO
2NHCH(CH
3)
2H OCH
3OCH
3CH
6-F SO
2NHCH(CH
3)
2H OCH
3OCH
3CH
6-Cl SO
2NHCH(CH
3)
2H OCH
3OCH
3CH
Table II (continuing)
R
1R
3R X Y Z m.p.(℃)
H SO
2NH-cyclopropyl H OCH
3OCH
3CH
H SO
2NH-cyclopropyl H OCH
3CH
3CH
H SO
2NH-cyclopropyl H Cl OCH
3CH
H SO
2NH-cyclopropyl H CH
3CH
3CH
H SO
2NH-cyclopropyl H OCH
3OCH
3N
H SO
2NH-cyclopropyl H OCH
3CH
3N
H SO
2NH-cyclopropyl H OCH
2CH
3NHCH
3N
H SO
2NH-cyclopropyl CH
3OCH
3CH
3N
4-CH
3SO
2NH-cyclopropyl H OCH
3OCH
3CH
4-Cl SO
2NH-cyclopropyl H OCH
3OCH
3CH
6-CH
3SO
2NH-cyclopropyl H OCH
3OCH
3CH
6-OCH
3SO
2NH-cyclopropyl H OCH
3OCH
3CH
6-F SO
2NH-cyclopropyl H OCH
3OCH
3CH
6-Cl SO
2NH-cyclopropyl H OCH
3OCH
3CH
H SO
2NHCH
2CH=CH
2H OCH
3OCH
3CH
H SO
2NHCH
2CH=CH
2H OCH
3CH
3CH
H SO
2NHCH
2CH=CH
2H Cl OCH
3CH
H SO
2NHCH
2CH=CH
2H CH
3CH
3CH
H SO
2NHCH
2CH=CH
2H OCH
3OCH
3N
H SO
2NHCH
2CH=CH
2H OCH
3CH
3N
H SO
2NHCH
2CH=CH
2H OCH
2CH
3NHCH
3N
H SO
2NHCH
2CH=CH
2CH
3OCH
3CH
3N
4-CH
3SO
2NHCH
2CH=CH
2H OCH
3OCH
3CH
4-Cl SO
2NHCH
2CH=CH
2H OCH
3OCH
3CH
6-CH
3SO
2NHCH
2CH=CH
2H OCH
3OCH
3CH
6-OCH
3SO
2NHCH
2CH=CH
2H OCH
3OCH
3CH
6-F SO
2NHCH
2CH=CH
2H OCH
3OCH
3CH
6-Cl SO
2NHCH
2CH=CH
2H OCH
3OCH
3CH
Table II (continuing)
R
1R
3R X Y Z m.p.(℃)
H SO
2NHCH
2CF
3H OCH
3OCH
3CH
H SO
2NHCH
2CF
3H OCH
3CH
3CH
H SO
2NHCH
2CF
3H Cl OCH
3CH
H SO
2NHCH
2CF
3H CH
3CH
3CH
H SO
2NHCH
2CF
3H OCH
3OCH
3N
H SO
2NHCH
2CF
3H OCH
3CH
3N
H SO
2NHCH
2CF
3H OCH
2CH
3NHCH
3N
H SO
2NHCH
2CF
3CH
3OCH
3CH
3N
4-CH
3SO
2NHCH
2CF
3H OCH
3OCH
3CH
4-Cl SO
2NHCH
2CF
3H OCH
3OCH
3CH
6-CH
3SO
2NHCH
2CF
3H OCH
3OCH
3CH
6-OCH
3SO
2NHCH
2CF
3H OCH
3OCH
3CH
6-F SO
2NHCH
2CF
3H OCH
3OCH
3CH
6-Cl SO
2NHCH
2CF
3H OCH
3OCH
3CH
H SO
2NHCH
2CN H OCH
3OCH
3CH
H SO
2NHCH
2CN H OCH
3CH
3CH
H SO
2NHCH
2CN H Cl OCH
3CH
H SO
2NHCH
2CN H CH
3CH
3CH
H SO
2NHCH
2CN H OCH
3OCH
3N
H SO
2NHCH
2CN H OCH
3CH
3N
H SO
2NHCH
2CN H OCH
2CH
3NHCH
3N
H SO
2NHCH
2CN CH
3OCH
3CH
3N
4-CH
3SO
2NHCH
2CN H OCH
3OCH
3CH
4-Cl SO
2NHCH
2CN H OCH
3OCH
3CH
6-CH
3SO
2NHCH
2CN H OCH
3OCH
3CH
6-OCH
3SO
2NHCH
2CN H OCH
3OCH
3CH
6-F SO
2NHCH
2CN H OCH
3OCH
3CH
6-Cl SO
2NHCH
2CN H OCH
3OCH
3CH
Table II (continuing)
R
1R
3R X Y Z m.p.(℃)
H SO
2N(CH
2CH=CH
2)
2H OCH
3OCH
3CH
H SO
2N(CH
2CH=CH
2)
2H OCH
3CH
3CH
H SO
2N(CH
2CH=CH
2)
2H Cl OCH
3CH
H SO
2N(CH
2CH=CH
2)
2H CH
3CH
3CH
H SO
2N(CH
2CH=CH
2)
2H OCH
3OCH
3N
H SO
2N(CH
2CH=CH
2)
2H OCH
3CH
3N
H SO
2N(CH
2CH=CH
2)
2H OCH
2CH
3NHCH
3N
H SO
2N(CH
2CH=CH
2)
2CH
3OCH
3CH
3N
4-CH
3SO
2N(CH
2CH=CH
2)
2H OCH
3OCH
3CH
4-Cl SO
2N(CH
2CH=CH
2)
2H OCH
3OCH
3CH
6-CH
3SO
2N(CH
2CH=CH
2)
2H OCH
3OCH
3CH
6-OCH
3SO
2N(CH
2CH=CH
2)
2H OCH
3OCH
3CH
6-F SO
2N(CH
2CH=CH
2)
2H OCH
3OCH
3CH
6-Cl SO
2N(CH
2CH=CH
2)
2H OCH
3OCH
3CH
H SO
2-pyrrolidyl H OCH
3OCH
3CH
H SO
2-pyrrolidyl H OCH
3CH
3CH
H SO
2-pyrrolidyl H Cl OCH
3CH
H SO
2-pyrrolidyl H CH
3CH
3CH
H SO
2-pyrrolidyl H OCH
3OCH
3N
H SO
2-pyrrolidyl H OCH
3CH
3N
H SO
2-pyrrolidyl H OCH
2CH
3NHCH
3N
H SO
2-pyrrolidyl CH
3OCH
3CH
3N
4-CH
3SO
2-pyrrolidyl H OCH
3OCH
3CH
4-Cl SO
2-pyrrolidyl H OCH
3OCH
3CH
6-CH
3SO
2-pyrrolidyl H OCH
3OCH
3CH
6-OCH
3SO
2-pyrrolidyl H OCH
3OCH
3CH
6-F SO
2-pyrrolidyl H OCH
3OCH
3CH
6-Cl SO
2-pyrrolidyl H OCH
3OCH
3CH
Table II (continuing)
R
1R
3R X Y Z m.p.(℃)
H SO
2NHCH
2CH
2OCH
3H OCH
3OCH
3CH
H SO
2NHCH
2CH
2OCH
3H OCH
3CH
3CH
H SO
2NHCH
2CH
2OCH
3H Cl OCH
3CH
H SO
2NHCH
2CH
2OCH
3H CH
3CH
3CH
H SO
2NHCH
2CH
2OCH
3H OCH
3OCH
3N
H SO
2NHCH
2CH
2OCH
3H OCH
3CH
3N
H SO
2NHCH
2CH
2OCH
3H OCH
2CH
3NHCH
3N
H SO
2NHCH
2CH
2OCH
3CH
3OCH
3CH
3N
4-CH
3SO
2NHCH
2CH
2OCH
3H OCH
3OCH
3CH
4-Cl SO
2NHCH
2CH
2OCH
3H OCH
3OCH
3CH
6-CH
3SO
2NHCH
2CH
2OCH
3H OCH
3OCH
3CH
6-OCH
3SO
2NHCH
2CH
2OCH
3H OCH
3OCH
3CH
6-F SO
2NHCH
2CH
2OCH
3H OCH
3OCH
3CH
6-Cl SO
2NHCH
2CH
2OCH
3H OCH
3OCH
3CH
H SO
2NH
2H OCH
3OCH
3CH
H SO
2NH
2H OCH
3CH
3CH
H SO
2NH
2H Cl OCH
3CH
H SO
2NH
2H CH
3CH
3CH
H SO
2NH
2H OCH
3OCH
3N
H SO
2NH
2H OCH
3CH
3N
H SO
2NH
2H OCH
2CH
3NHCH
3N
H SO
2NH
2CH
3OCH
3CH
3N
4-CH
3SO
2NH
2H OCH
3OCH
3CH
4-Cl SO
2NH
2H OCH
3OCH
3CH
6-CH
3SO
2NH
2H OCH
3OCH
3CH
6-OCH
3SO
2NH
2H OCH
3OCH
3CH
6-F SO
2NH
2H OCH
3OCH
3CH
6-Cl SO
2NH
2H OCH
3OCH
3CH
Table II (continuing)
R
1R
3R X Y Z m.p.(℃)
H CO
2CH
2CH
2OH H OCH
3OCH
3CH
H CO
2CH
2CH
2OH H OCH
3CH
3CH
H CO
2CH
2CH
2OH H Cl OCH
3CH
H CO
2CH
2CH
2OH H CH
3CH
3CH
H CO
2CH
2CH
2OH H OCH
3OCH
3N
H CO
2CH
2CH
2OH H OCH
3CH
3N
H CO
2CH
2CH
2OH H OCH
2CH
3NHCH
3N
H CO
2CH
2CH
2OH CH
3OCH
3CH
3N
4-CH
3CO
2CH
2CH
2OH H OCH
3OCH
3CH
4-Cl CO
2CH
2CH
2OH H OCH
3OCH
3CH
6-CH
3CO
2CH
2CH
2OH H OCH
3OCH
3CH
6-OCH
3CO
2CH
2CH
2OH H OCH
3OCH
3CH
6-F CO
2CH
2CH
2OH H OCH
3OCH
3CH
6-Cl CO
2CH
2CH
2OH H OCO
3OCH
3CH
H CO
2CH
2CH
2CN H OCH
3OCH
3CH
H CO
2CH
2CH
2CN H OCH
3CH
3CH
H CO
2CH
2CH
2CN H Cl OCH
3CH
H CO
2CH
2CH
2CN H CH
3CH
3CH
H CO
2CH
2CH
2CN H OCH
3OCH
3N
H CO
2CH
2CH
2CN H OCH
3CH
3N
H CO
2CH
2CH
2CN H OCH
2CH
3NHCH
3N
H CO
2CH
2CH
2CN CH
3OCH
3CH
3N
4-CH
3CO
2CH
2CH
2CN H OCH
3OCH
3CH
4-Cl CO
2CH
2CH
2CN H OCH
3OCH
3CH
6-CH
3CO
2CH
2CH
2CN H OCH
3OCH
3CH
6-OCH
3CO
2CH
2CH
2CN H OCH
3OCH
3CH
6-F CO
2CH
2CH
2CN H OCH
3OCH
3CH
6-Cl CO
2CH
2CH
2CN H OCH
3OCH
3CH
Table II (continuing)
R
1R
3R X Y Z m.p.(℃)
H CO
2CH
2CH
2OSO
2CH
3H OCH
3OCH
3CH
H CO
2CH
2CH
2OSO
2CH
3H OCH
3CH
3CH
H CO
2CH
2CH
2OSO
2CH
3H Cl OCH
3CH
H CO
2CH
2CH
2OSO
2CH
3H CH
3CH
3CH
H CO
2CH
2CH
2OSO
2CH
3H OCH
3OCH
3N
H CO
2CH
2CH
2OSO
2CH
3H OCH
3CH
3N
H CO
2CH
2CH
2OSO
2CH
3H OCH
2CH
3NHCH
3N
H CO
2CH
2CH
2OSO
2CH
3CH
3OCH
3CH
3N
4-CH
3CO
2CH
2CH
2OSO
2CH
3H OCH
3OCH
3CH
4-Cl CO
2CH
2CH
2OSO
2CH
3H OCH
3OCH
3CH
6-CH
3CO
2CH
2CH
2OSO
2CH
3H OCH
3OCH
3CH
6-OCH
3CO
2CH
2CH
2OSO
2CH
3H OCH
3OCH
3CH
6-F CO
2CH
2CH
2OSO
2CH
3H OCH
3OCH
3CH
6-Cl CO
2CH
2CH
2OSO
2CH
3H OCO
3OCH
3CH
H CO
2CH
2CF
3H OCH
3OCH
3CH
H CO
2CH
2CF
3H OCH
3CH
3CH
H CO
2CH
2CF
3H Cl OCH
3CH
H CO
2CH
2CF
3H CH
3CH
3CH
H CO
2CH
2CF
3H OCH
3OCH
3N
H CO
2CH
2CF
3H OCH
3CH
3N
H CO
2CH
2CF
3H OCH
2CH
3NHCH
3N
H CO
2CH
2CF
3CH
3OCH
3CH
3N
4-CH
3CO
2CH
2CF
3H OCH
3OCH
3CH
4-Cl CO
2CH
2CF
3H OCH
3OCH
3CH
6-CH
3CO
2CH
2CF
3H OCH
3OCH
3CH
6-OCH
3CO
2CH
2CF
3H OCH
3OCH
3CH
6-F CO
2CH
2CF
3H OCH
3OCH
3CH
6-Cl CO
2CH
2CF
3H OCH
3OCH
3CH
The table III
General formula 3
R
fR
4R X Y Z m.p.(℃)
H SOCH
3H OCH
3OCH
3CH
H SOCH
3H OCH
3CH
3CH
H SOCH
3H Cl OCH
3CH
H SOCH
3H CH
3CH
3CH
H SOCH
3H OCH
3OCH
3N
H SOCH
3H OCH
3CH
3N
H SOCH
3CH
3OCH
3CH
3N
2-Cl SOCH
3H OCH
3OCH
3CH
2-F SOCH
3H OCH
3OCH
3CH
6-CH
3SOCH
3H OCH
3OCH
3CH
6-OCH
3SOCH
3H OCH
3OCH
3CH
6-F SOCH
3H OCH
3OCH
3CH
6-Cl SOCH
3H OCH
3OCH
3CH
H SOCH
2CH
3H OCH
3OCH
3CH
H SOCH
2CH
3H OCH
3CH
3CH
H SOCH
2CH
3H Cl OCH
3CH
H SOCH
2CH
3H CH
3CH
3CH
H SOCH
2CH
3H OCH
3OCH
3N
H SOCH
2CH
3H OCH
3CH
3N
H SOCH
2CH
3CH
3OCH
3CH
3N
2-Cl SOCH
2CH
3H OCH
3OCH
3CH
2-F SOCH
2CH
3H OCH
3OCH
3CH
6-CH
3SOCH
2CH
3H OCH
3OCH
3CH
6-OCH
3SOCH
2CH
3H OCH
3OCH
3CH
6-F SOCH
2CH
3H OCH
3OCH
3CH
6-Cl SOCH
2CH
3H OCH
3OCH
3CH
Table III (continuing)
R
fR
4R X Y Z m.p.(℃)
H SOCH
2CH
2CH
3H OCH
3OCH
3CH
H SOCH
2CH
2CH
3H OCH
3CH
3CH
H SOCH
2CH
2CH
3H Cl OCH
3CH
H SOCH
2CH
2CH
3H CH
3CH
3CH
H SOCH
2CH
2CH
3H OCH
3OCH
3N
H SOCH
2CH
2CH
3H OCH
3CH
3N
H SOCH
2CH
2CH
3CH
3OCH
3CH
3N
2-Cl SOCH
2CH
2CH
3H OCH
3OCH
3CH
2-F SOCH
2CH
2CH
3H OCH
3OCH
3CH
6-CH
3SOCH
2CH
2CH
3H OCH
3OCH
3CH
6-OCH
3SOCH
2CH
2CH
3H OCH
3OCH
3CH
6-F SOCH
2CH
2CH
3H OCH
3OCH
3CH
6-Cl SOCH
2CH
2CH
3H OCH
3OCH
3CH
H SOCH
2CH
2CH
2CH
3H OCH
3OCH
3CH
H SOCH
2CH
2CH
2CH
3H OCH
3CH
3CH
H SOCH
2CH
2CH
2CH
3H Cl OCH
3CH
H SOCH
2CH
2CH
2CH
3H CH
3CH
3CH
H SOCH
2CH
2CH
2CH
3H OCH
3OCH
3N
H SOCH
2CH
2CH
2CH
3H OCH
3CH
3N
H SOCH
2CH
2CH
2CH
3CH
3OCH
3CH
3N
2-Cl SOCH
2CH
2CH
2CH
3H OCH
3OCH
3CH
2-F SOCH
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-CH
3SOCH
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-OCH
3SOCH
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-F SOCH
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-Cl SOCH
2CH
2CH
2CH
3H OCH
3OCH
3CH
Table III (continuing)
R
fR
4R X Y Z m.p.(℃)
H SOCH(CH
3)
2H OCH
3OCH
3CH
H SOCH(CH
3)
2H OCH
3CH
3CH
H SOCH(CH
3)
2H Cl OCH
3CH
H SOCH(CH
3)
2H CH
3CH
3CH
H SOCH(CH
3)
2H OCH
3OCH
3N
H SOCH(CH
3)
2H OCH
3CH
3N
H SOCH(CH
3)
2CH
3OCH
3CH
3N
2-Cl SOCH(CH
3)
2H OCH
3OCH
3CH
2-F SOCH(CH
3)
2H OCH
3OCH
3CH
6-CH
3SOCH(CH
3)
2H OCH
3OCH
3CH
6-OCH
3SOCH(CH
3)
2H OCH
3OCH
3CH
6-F SOCH(CH
3)
2H OCH
3OCH
3CH
6-Cl SOCH(CH
3)
2H OCH
3OCH
3CH
H S-cyclopropyl H OCH
3OCH
3CH
H S-cyclopropyl H OCH
3CH
3CH
H S-cyclopropyl H Cl OCH
3CH
H S-cyclopropyl H CH
3CH
3CH
H S-cyclopropyl H OCH
3OCH
3N
H S-cyclopropyl H OCH
3CH
3N
H S-cyclopropyl H OCH
2CH
3NHCH
3N
H S-cyclopropyl CH
3OCH
3CH
3N
2-Cl S-cyclopropyl H OCH
3OCH
3CH
2-F S-cyclopropyl H OCH
3OCH
3CH
6-CH
3S-cyclopropyl H OCH
3OCH
3CH
6-OCH
3S-cyclopropyl H OCH
3OCH
3CH
6-F S-cyclopropyl H OCH
3OCH
3CH
6-Cl S-cyclopropyl H OCH
3OCH
3CH
Table III (continuing)
R
fR
4R X Y Z m.p.(℃)
H SO-cyclopropyl H OCH
3OCH
3CH
H SO-cyclopropyl H OCH
3CH
3CH
H SO-cyclopropyl H Cl OCH
3CH
H SO-cyclopropyl H CH
3CH
3CH
H SO-cyclopropyl H OCH
3OCH
3N
H SO-cyclopropyl H OCH
3CH
3N
H SO-cyclopropyl H OCH
2CH
3NHCH
3N
H SO-cyclopropyl CH
3OCH
3CH
3N
2-Cl SO-cyclopropyl H OCH
3OCH
3CH
2-F SO-cyclopropyl H OCH
3OCH
3CH
6-CH
3SO-cyclopropyl H OCH
3OCH
3CH
6-OCH
3SO-cyclopropyl H OCH
3OCH
3CH
6-F SO-cyclopropyl H OCH
3OCH
3CH
6-Cl SO-cyclopropyl H OCH
3OCH
3CH
H SO
2-cyclopropyl H OCH
3OCH
3CH
H SO
2-cyclopropyl H OCH
3CH
3CH
H SO
2-cyclopropyl H Cl OCH
3CH
H SO
2-cyclopropyl H CH
3CH
3CH
H SO
2-cyclopropyl H OCH
3OCH
3N
H SO
2-cyclopropyl H OCH
3CH
3N
H SO
2-cyclopropyl H OCH
2CH
3NHCH
3N
H SO
2-cyclopropyl CH
3OCH
3CH
3N
2-Cl SO
2-cyclopropyl H OCH
3OCH
3CH
2-F SO
2-cyclopropyl H OCH
3OCH
3CH
6-CH
3SO
2-cyclopropyl H OCH
3OCH
3CH
6-OCH
3SO
2-cyclopropyl H OCH
3OCH
3CH
6-F SO
2-cyclopropyl H OCH
3OCH
3CH
6-Cl SO
2-cyclopropyl H OCH
3OCH
3CH
Table III (continuing)
R
fR
4R X Y Z m.p.(℃)
H OSO
2CH
3H OCH
3OCH
3CH
H OSO
2CH
3H OCH
3CH
3CH
H OSO
2CH
3H Cl OCH
3CH
H OSO
2CH
3H CH
3CH
3CH
H OSO
2CH
3H OCH
3OCH
3N
H OSO
2CH
3H OCH
3CH
3N
H OSO
2CH
3H OCH
2CH
3NHCH
3N
H OSO
2CH
3CH
3OCH
3CH
3N
2-Cl OSO
2CH
3H OCH
3OCH
3CH
2-F OSO
2CH
3H OCH
3OCH
3CH
6-CH
3OSO
2CH
3H OCH
3OCH
3CH
6-OCH
3OSO
2CH
3H OCH
3OCH
3CH
6-F OSO
2CH
3H OCH
3OCH
3CH
6-Cl OSO
2CH
3H OCH
3OCH
3CH
H OSO
2CH
2CH
3H OCH
3OCH
3CH
H OSO
2CH
2CH
3H OCH
3CH
3CH
H OSO
2CH
2CH
3H Cl OCH
3CH
H OSO
2CH
2CH
3H CH
3CH
3CH
H OSO
2CH
2CH
3H OCH
3OCH
3N
H OSO
2CH
2CH
3H OCH
3CH
3N
H OSO
2CH
2CH
3H OCH
2CH
3NHCH
3N
H OSO
2CH
2CH
3CH
3OCH
3CH
3N
2-Cl OSO
2CH
2CH
3H OCH
3OCH
3CH
2-F OSO
2CH
2CH
3H OCH
3OCH
3CH
6-CH
3OSO
2CH
2CH
3H OCH
3OCH
3CH
6-OCH
3OSO
2CH
2CH
3H OCH
3OCH
3CH
6-F OSO
2CH
2CH
3H OCH
3OCH
3CH
6-Cl OSO
2CH
2CH
3H OCH
3OCH
3CH
Table III (continuing)
R
fR
4R X Y Z m.p.(℃)
H OSO
2CH
2CH
2CH
3H OCH
3OCH
3CH
H OSO
2CH
2CH
2CH
3H OCH
3CH
3CH
H OSO
2CH
2CH
2CH
3H Cl OCH
3CH
H OSO
2CH
2CH
2CH
3H CH
3CH
3CH
H OSO
2CH
2CH
2CH
3H OCH
3OCH
3N
H OSO
2CH
2CH
2CH
3H OCH
3CH
3N
H OSO
2CH
2CH
2CH
3H OCH
2CH
3NHCH
3N
H OSO
2CH
2CH
2CH
3CH
3OCH
3CH
3N
2-Cl OSO
2CH
2CH
2CH
3H OCH
3OCH
3CH
2-F OSO
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-CH
3OSO
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-OCH
3OSO
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-F OSO
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-Cl OSO
2CH
2CH
2CH
3H OCH
3OCH
3CH
H OSO
2CF
3H OCH
3OCH
3CH
H OSO
2CF
3H OCH
3CH
3CH
H OSO
2CF
3H Cl OCH
3CH
H OSO
2CF
3H CH
3CH
3CH
H OSO
2CF
3H OCH
3OCH
3N
H OSO
2CF
3H OCH
3CH
3N
H OSO
2CF
3H OCH
2CH
3NHCH
3N
H OSO
2CF
3CH
3OCH
3CH
3N
2-Cl OSO
2CF
3H OCH
3OCH
3CH
2-F OSO
2CF
3H OCH
3OCH
3CH
6-CH
3OSO
2CF
3H OCH
3OCH
3CH
6-OCH
3OSO
2CF
3H OCH
3OCH
3CH
6-F OSO
2CF
3H OCH
3OCH
3CH
6-Cl OSO
2CF
3H OCH
3OCH
3CH
Table III (continuing)
R
fR
4R X Y Z m.p.(℃)
H OSO
2CCl
3H OCH
3OCH
3CH
H OSO
2CCl
3H OCH
3CH
3CH
H OSO
2CCl
3H Cl OCH
3CH
H OSO
2CCl
3H CH
3CH
3CH
H OSO
2CCl
3H OCH
3OCH
3N
H OSO
2CCl
3H OCH
3CH
3N
H OSO
2CCl
3H OCH
2CH
3NHCH
3N
H OSO
2CCl
3CH
3OCH
3CH
3N
2-Cl OSO
2CCl
3H OCH
3OCH
3CH
2-F OSO
2CCl
3H OCH
3OCH
3CH
6-CH
3OSO
2CCl
3H OCH
3OCH
3CH
6-OCH
3OSO
2CCl
3H OCH
3OCH
3CH
6-F OSO
2CCl
3H OCH
3OCH
3CH
6-Cl OSO
2CCl
3H OCH
3OCH
3CH
H N
3H OCH
3OCH
3CH
H N
3H OCH
3CH
3CH
H N
3H Cl OCH
3CH
H N
3H CH
3CH
3CH
H N
3H OCH
3OCH
3N
H N
3H OCH
3CH
3N
H N
3H OCH
2CH
3NHCH
3N
H N
3CH
3OCH
3CH
3N
2-Cl N
3H OCH
3OCH
3CH
2-F N
3H OCH
3OCH
3CH
6-CH
3N
3H OCH
3OCH
3CH
6-OCH
3N
3H OCH
3OCH
3CH
6-F N
3H OCH
3OCH
3CH
6-Cl N
3H OCH
3OCH
3CH
Table III (continuing)
R
fR
4R X Y Z m.p.(℃)
H P(O)(OCH
3)
2H OCH
3OCH
3CH
H P(O)(OCH
3)
2H OCH
3CH
3CH
H P(O)(OCH
3)
2H Cl OCH
3CH
H P(O)(OCH
3)
2H CH
3CH
3CH
H P(O)(OCH
3)
2H OCH
3OCH
3N
H P(O)(OCH
3)
2H OCH
3CH
3N
H P(O)(OCH
3)
2H OCH
2CH
3NHCH
3N
H P(O)(OCH
3)
2CH
3OCH
3CH
3N
2-Cl P(O)(OCH
3)
2H OCH
3OCH
3CH
2-F P(O)(OCH
3)
2H OCH
3OCH
3CH
6-CH
3P(O)(OCH
3)
2H OCH
3OCH
3CH
6-OCH
3P(O)(OCH
3)
2H OCH
3OCH
3CH
6-F P(O)(OCH
3)
2H OCH
3OCH
3CH
6-Cl P(O)(OCH
3)
2H OCH
3OCH
3CH
H CN H OCH
3OCH
3CH
H CN H OCH
3CH
3CH
H CN H Cl OCH
3CH
H CN H CH
3CH
3CH
H CN H OCH
3OCH
3CN
H CN H OCH
3CH
3CN
H CN H OCH
2CH
3NHCH
3CN
H CN CH
3OCH
3CH
3CN
2-Cl CN H OCH
3OCH
3CH
2-F CN H OCH
3OCH
3CH
6-CH
3CN H OCH
3OCH
3CH
6-OCH
3CN H OCH
3OCH
3CH
6-F CN H OCH
3OCH
3CH
6-Cl CN H OCH
3OCH
3CH
Table III (continuing)
R
fR
4R X Y Z m.p.(℃)
H CH
2F H OCH
3OCH
3CH
H CH
2F H OCH
3CH
3CH
H CH
2F H Cl OCH
3CH
H CH
2F H CH
3CH
3CH
H CH
2F H OCH
3OCH
3N
H CH
2F H OCH
3CH
3N
H CH
2F H OCH
2CH
3NHCH
3N
H CH
2F CH
3OCH
3CH
3N
2-Cl CH
2F H OCH
3OCH
3CH
2-F CH
2F H OCH
3OCH
3CH
6-CH
3CH
2F H OCH
3OCH
3CH
6-OCH
3CH
2F H OCH
3OCH
3CH
6-F CH
2F H OCH
3OCH
3CH
6-Cl CH
2F H OCH
3OCH
3CH
H CF
2H H OCH
3OCH
3CH
H CF
2H H OCH
3CH
3CH
H CF
2H H Cl OCH
3CH
H CF
2H H CH
3CH
3CH
H CF
2H H OCH
3OCH
3N
H CF
2H H OCH
3CH
3N
H CF
2H H OCH
3OCH
3N
H CF
2H CH
3OCH
3CH
3N
2-Cl CF
2H H OCH
3OCH
3CH
2-F CF
2H H OCH
3OCH
3CH
6-CH
3CF
2H H OCH
3OCH
3CH
6-OCH
3CF
2H H OCH
3OCH
3CH
6-F CF
2H H OCH
3OCH
3CH
6-Cl CF
2H H OCH
3OCH
3CH
Table III (continuing)
R
fR
4R X Y Z m.p.(℃)
H SO
2N(OCH
3)CH
3H OCH
3OCH
3CH
H SO
2N(OCH
3)CH
3H OCH
3CH
3CH
H SO
2N(OCH
3)CH
3H Cl OCH
3CH
H SO
2N(OCH
3)CH
3H CH
3CH
3CH
H SO
2N(OCH
3)CH
3H OCH
3OCH
3N
H SO
2N(OCH
3)CH
3H OCH
3CH
3N
H SO
2N(OCH
3)CH
3H OCH
2CH
3NHCH
3N
H SO
2N(OCH
3)CH
3CH
3OCH
3CH
3N
2-Cl SO
2N(OCH
3)CH
3H OCH
3OCH
3CH
2-F SO
2N(OCH
3)CH
3H OCH
3OCH
3CH
6-CH
3SO
2N(OCH
3)CH
3H OCH
3OCH
3CH
6-OCH
3SO
2N(OCH
3)CH
3H OCH
3OCH
3CH
6-F SO
2N(OCH
3)CH
3H OCH
3OCH
3CH
6-Cl SO
2N(OCH
3)CH
3H OCH
3OCH
3CH
H SO
2NHCH
3H OCH
3OCH
3CH
H SO
2NHCH
3H OCH
3CH
3CH
H SO
2NHCH
3H Cl OCH
3CH
H SO
2NHCH
3H CH
3CH
3CH
H SO
2NHCH
3H OCH
3OCH
3N
H SO
2NHCH
3H OCH
3CH
3N
H SO
2NHCH
3H OCH
2CH
3NHCH
3N
H SO
2NHCH
3CH
3OCH
3CH
3N
2-Cl SO
2NHCH
3H OCH
3OCH
3CH
2-F SO
2NHCH
3H OCH
3OCH
3CH
6-CH
3SO
2NHCH
3H OCH
3OCH
3CH
6-OCH
3SO
2NHCH
3H OCH
3OCH
3CH
6-F SO
2NHCH
3H OCH
3OCH
3CH
6-Cl SO
2NHCH
3H OCH
3OCH
3CH
Table III (continuing)
R
fR
4R X Y Z m.p.(℃)
H SO
2NHCH
2CH
3H OCH
3OCH
3CH
H SO
2NHCH
2CH
3H OCH
3CH
3CH
H SO
2NHCH
2CH
3H Cl OCH
3CH
H SO
2NHCH
2CH
3H CH
3CH
3CH
H SO
2NHCH
2CH
3H OCH
3OCH
3N
H SO
2NHCH
2CH
3H OCH
3CH
3N
H SO
2NHCH
2CH
3H OCH
2CH
3NHCH
3N
H SO
2NHCH
2CH
3CH
3OCH
3CH
3N
2-Cl SO
2NHCH
2CH
3H OCH
3OCH
3CH
2-F SO
2NHCH
2CH
3H OCH
3OCH
3CH
6-CH
3SO
2NHCH
2CH
3H OCH
3OCH
3CH
6-OCH
3SO
2NHCH
2CH
3H OCH
3OCH
3CH
6-F SO
2NHCH
2CH
3H OCH
3OCH
3CH
6-Cl SO
2NHCH
2CH
3H OCH
3OCH
3CH
H SO
2NHCH
2CH
2OCH
3H OCH
3OCH
3CH
H SO
2NHCH
2CH
2OCH
3H OCH
3CH
3CH
H SO
2NHCH
2CH
2OCH
3H Cl OCH
3CH
H SO
2NHCH
2CH
2OCH
3H CH
3CH
3CH
H SO
2NHCH
2CH
2OCH
3H OCH
3OCH
3N
H SO
2NHCH
2CH
2OCH
3H OCH
3CH
3N
H SO
2NHCH
2CH
2OCH
3H OCH
2CH
3NHCH
3N
H SO
2NHCH
2CH
2OCH
3CH
3OCH
3CH
3N
2-Cl SO
2NHCH
2CH
2OCH
3H OCH
3OCH
3CH
2-F SO
2NHCH
2CH
2OCH
3H OCH
3OCH
3CH
6-CH
3SO
2NHCH
2CH
2OCH
3H OCH
3OCH
3CH
6-OCH
3SO
2NHCH
2CH
2OCH
3H OCH
3OCH
3CH
6-F SO
2NHCH
2CH
2OCH
3H OCH
3OCH
3CH
6-Cl SO
2NHCH
2CH
2OCH
3H OCH
3OCH
3CH
Table III (continuing)
R
fR
4R X Y Z m.p.(℃)
H CO
2CH
2CH
2OH H OCH
3OCH
3CH
H CO
2CH
2CH
2OH H OCH
3CH
3CH
H CO
2CH
2CH
2OH H Cl OCH
3CH
H CO
2CH
2CH
2OH H CH
3CH
3CH
H CO
2CH
2CH
2OH H OCH
3OCH
3N
H CO
2CH
2CH
2OH H OCH
3CH
3N
H CO
2CH
2CH
2OH H OCH
2CH
3NHCH
3N
H CO
2CH
2CH
2OH CH
3OCH
3CH
3N
2-Cl CO
2CH
2CH
2OH H OCH
3OCH
3CH
2-F CO
2CH
2CH
2OH H OCH
3OCH
3CH
6-CH
3CO
2CH
2CH
2OH H OCH
3OCH
3CH
6-OCH
3CO
2CH
2CH
2OH H OCH
3OCH
3CH
6-F CO
2CH
2CH
2OH H OCH
3OCH
3CH
6-Cl CO
2CH
2CH
2OH H OCH
3OCH
3CH
H CO
2CH
2CH
2CN H OCH
3OCH
3CH
H CO
2CH
2CH
2CN H OCH
3CH
3CH
H CO
2CH
2CH
2CN H Cl OCH
3CH
H CO
2CH
2CH
2CN H CH
3CH
3CH
H CO
2CH
2CH
2CN H OCH
3OCH
3N
H CO
2CH
2CH
2CN H OCH
3CH
3N
H CO
2CH
2CH
2CN H OCH
3OCH
3N
H CO
2CH
2CH
2CN CH
3OCH
3CH
3N
2-Cl CO
2CH
2CH
2CN H OCH
3OCH
3CH
2-F CO
2CH
2CH
2CN H OCH
3OCH
3CH
6-CH
3CO
2CH
2CH
2CN H OCH
3OCH
3CH
6-OCH
3CO
2CH
2CH
2CN H OCH
3OCH
3CH
6-F CO
2CH
2CH
2CN H OCH
3OCH
3CH
6-Cl CO
2CH
2CH
2CN H OCH
3OCH
3CH
Table III (continuing)
R
fR
4R X Y Z m.p.(℃)
H CO
2CH
2CH
2OSO
2CH
3H OCH
3OCH
3CH
H CO
2CH
2CH
2OSO
2CH
3H OCH
3CH
3CH
H CO
2CH
2CH
2OSO
2CH
3H Cl OCH
3CH
H CO
2CH
2CH
2OSO
2CH
3H CH
3CH
3CH
H CO
2CH
2CH
2OSO
2CH
3H OCH
3OCH
3N
H CO
2CH
2CH
2OSO
2CH
3H OCH
3CH
3N
H CO
2CH
2CH
2OSO
2CH
3H OCH
2CH
3NHCH
3N
H CO
2CH
2CH
2OSO
2CH
3CH
3OCH
3CH
3N
2-Cl CO
2CH
2CH
2OSO
2CH
3H OCH
3OCH
3CH
2-F CO
2CH
2CH
2OSO
2CH
3H OCH
3OCH
3CH
6-CH
3CO
2CH
2CH
2OSO
2CH
3H OCH
3OCH
3CH
6-OCH
3CO
2CH
2CH
2OSO
2CH
3H OCH
3OCH
3CH
6-F CO
2CH
2CH
2OSO
2CH
3H OCH
3OCH
3CH
6-Cl CO
2CH
2CH
2OSO
2CH
3H OCH
3OCH
3CH
H CO
2CH
2CF
3H OCH
3OCH
3CH
H CO
2CH
2CF
3H OCH
3CH
3CH
H CO
2CH
2CF
3H Cl OCH
3CH
H CO
2CH
2CF
3H CH
3CH
3CH
H CO
2CH
2CF
3H OCH
3OCH
3N
H CO
2CH
2CF
3H OCH
3CH
3N
H CO
2CH
2CF
3H OCH
3OCH
3N
H CO
2CH
2CF
3CH
3OCH
3CH
3N
2-Cl CO
2CH
2CF
3H OCH
3OCH
3CH
2-F CO
2CH
2CF
3H OCH
3OCH
3CH
6-CH
3CO
2CH
2CF
3H OCH
3OCH
3CH
6-OCH
3CO
2CH
2CF
3H OCH
3OCH
3CH
6-F CO
2CH
2CF
3H OCH
3OCH
3CH
6-Cl CO
2CH
2CF
3H OCH
3OCH
3CH
The table IV
General formula 4
R
fR
5R X Y Z m.p.(℃)
H SOCH
3H OCH
3OCH
3CH
H SOCH
3H OCH
3CH
3CH
H SOCH
3H Cl OCH
3CH
H SOCH
3H CH
3CH
3CH
H SOCH
3H OCH
3OCH
3N
H SOCH
3H OCH
3CH
3N
H SOCH
3H OCH
2CH
3NHCH
3N
H SOCH
3CH
3OCH
3CH
3N
5-CH
3SOCH
3H OCH
3OCH
3CH
5-OCH
3SOCH
3H OCH
3OCH
3CH
6-CH
3SOCH
3H OCH
3OCH
3CH
6-OCH
3SOCH
3H OCH
3OCH
3CH
6-F SOCH
3H OCH
3OCH
3CH
6-Cl SOCH
3H OCH
3OCH
3CH
H SO
2CH
3H OCH
3OCH
3CH
H SO
2CH
3H OCH
3CH
3CH
H SO
2CH
3H Cl OCH
3CH
H SO
2CH
3H CH
3CH
3CH
H SO
2CH
3H OCH
3OCH
3N
H SO
2CH
3H OCH
3CH
3N
H SO
2CH
3H OCH
2CH
3NHCH
3N
H SO
2CH
3CH
3OCH
3CH
3N
5-CH
3SO
2CH
3H OCH
3OCH
3CH
5-OCH
3SO
2CH
3H OCH
3OCH
3CH
6-CH
3SO
2CH
3H OCH
3OCH
3CH
6-OCH
3SO
2CH
3H OCH
3OCH
3CH
6-F SO
2CH
3H OCH
3OCH
3CH
6-Cl SO
2CH
3H OCH
3OCH
3CH
Table IV (continuing)
R
fR
5R X Y Z m.p.(℃)
H SOCH
2CH
3H OCH
3OCH
3CH
H SOCH
2CH
3H OCH
3CH
3CH
H SOCH
2CH
3H Cl OCH
3CH
H SOCH
2CH
3H CH
3CH
3CH
H SOCH
2CH
3H OCH
3OCH
3N
H SOCH
2CH
3H OCH
3CH
3N
H SOCH
2CH
3H OCH
2CH
3NHCH
3N
H SOCH
2CH
3CH
3OCH
3CH
3N
5-CH
3SOCH
2CH
3H OCH
3OCH
3CH
5-OCH
3SOCH
2CH
3H OCH
3OCH
3CH
6-CH
3SOCH
2CH
3H OCH
3OCH
3CH
6-OCH
3SOCH
2CH
3H OCH
3OCH
3CH
6-F SOCH
2CH
3H OCH
3OCH
3CH
6-Cl SOCH
2CH
3H OCH
3OCH
3CH
H SO
2CH
2CH
3H OCH
3OCH
3CH
H SO
2CH
2CH
3H OCH
3CH
3CH
H SO
2CH
2CH
3H Cl OCH
3CH
H SO
2CH
2CH
3H CH
3CH
3CH
H SO
2CH
2CH
3H OCH
3OCH
3N
H SO
2CH
2CH
3H OCH
3CH
3N
H SO
2CH
2CH
3H OCH
2CH
3NHCH
3N
H SO
2CH
2CH
3CH
3OCH
3CH
3N
5-CH
3SO
2CH
2CH
3H OCH
3OCH
3CH
5-OCH
3SO
2CH
2CH
3H OCH
3OCH
3CH
6-CH
3SO
2CH
2CH
3H OCH
3OCH
3CH
6-OCH
3SO
2CH
2CH
3H OCH
3OCH
3CH
6-F SO
2CH
2CH
3H OCH
3OCH
3CH
6-Cl SO
2CH
2CH
3H OCH
3OCH
3CH
Table IV (continuing)
R
fR
5R X Y Z m.p.(℃)
H SOCH
2CH
2CH
3H OCH
3OCH
3CH
H SOCH
2CH
2CH
3H OCH
3CH
3CH
H SOCH
2CH
2CH
3H Cl OCH
3CH
H SOCH
2CH
2CH
3H CH
3CH
3CH
H SOCH
2CH
2CH
3H OCH
3OCH
3N
H SOCH
2CH
2CH
3H OCH
3CH
3N
H SOCH
2CH
2CH
3H OCH
2CH
3NHCH
3N
H SOCH
2CH
2CH
3CH
3OCH
3CH
3N
5-CH
3SOCH
2CH
2CH
3H OCH
3OCH
3CH
5-OCH
3SOCH
2CH
2CH
3H OCH
3OCH
3CH
6-CH
3SOCH
2CH
2CH
3H OCH
3OCH
3CH
6-OCH
3SOCH
2CH
2CH
3H OCH
3OCH
3CH
6-F SOCH
2CH
2CH
3H OCH
3OCH
3CH
6-Cl SOCH
2CH
2CH
3H OCH
3OCH
3CH
H SO
2CH
2CH
2CH
3H OCH
3OCH
3CH
H SO
2CH
2CH
2CH
3H OCH
3CH
3CH
H SO
2CH
2CH
2CH
3H Cl OCH
3CH
H SO
2CH
2CH
2CH
3H CH
3CH
3CH
H SO
2CH
2CH
2CH
3H OCH
3OCH
3N
H SO
2CH
2CH
2CH
3H OCH
3CH
3N
H SO
2CH
2CH
2CH
3H OCH
2CH
3NHCH
3N
H SO
2CH
2CH
2CH
3CH
3OCH
3CH
3N
5-CH
3SO
2CH
2CH
2CH
3H OCH
3OCH
3CH
5-OCH
3SO
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-CH
3SO
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-OCH
3SO
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-F SO
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-Cl SO
2CH
2CH
2CH
3H OCH
3OCH
3CH
Table IV (continuing)
R
fR
5R X Y Z m.p.(℃)
H SOCH
2CH
2CH
2CH
3H OCH
3OCH
3CH
H SOCH
2CH
2CH
2CH
3H OCH
3CH
3CH
H SOCH
2CH
2CH
2CH
3H Cl OCH
3CH
H SOCH
2CH
2CH
2CH
3H CH
3CH
3CH
H SOCH
2CH
2CH
2CH
3H OCH
3OCH
3N
H SOCH
2CH
2CH
2CH
3H OCH
3CH
3N
H SOCH
2CH
2CH
2CH
3H OCH
2CH
3NHCH
3N
H SOCH
2CH
2CH
2CH
3CH
3OCH
3CH
3N
5-CH
3SOCH
2CH
2CH
2CH
3H OCH
3OCH
3CH
5-OCH
3SOCH
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-CH
3SOCH
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-OCH
3SOCH
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-F SOCH
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-Cl SOCH
2CH
2CH
2CH
3H OCH
3OCH
3CH
H SO
2CH
2CH
2CH
2CH
3H OCH
3OCH
3CH
H SO
2CH
2CH
2CH
2CH
3H OCH
3CH
3CH
H SO
2CH
2CH
2CH
2CH
3H Cl OCH
3CH
H SO
2CH
2CH
2CH
2CH
3H CH
3CH
3CH
H SO
2CH
2CH
2CH
2CH
3H OCH
3OCH
3N
H SO
2CH
2CH
2CH
2CH
3H OCH
3CH
3N
H SO
2CH
2CH
2CH
2CH
3H OCH
2CH
3NHCH
3N
H SO
2CH
2CH
2CH
2CH
3CH
3OCH
3CH
3N
5-CH
3SO
2CH
2CH
2CH
2CH
3H OCH
3OCH
3CH
5-OCH
3SO
2CH
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-CH
3SO
2CH
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-OCH
3SO
2CH
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-F SO
2CH
2CH
2CH
2CH
3H OCH
3OCH
3CH
6-Cl SO
2CH
2CH
2CH
2CH
3H OCH
3OCH
3CH
Table IV (continuing)
R
fR
5R X Y Z m.p.(℃)
H SOCH(CH
3)
2H OCH
3OCH
3CH
H SOCH(CH
3)
2H OCH
3CH
3CH
H SOCH(CH
3)
2H Cl OCH
3CH
H SOCH(CH
3)
2H CH
3CH
3CH
H SOCH(CH
3)
2H OCH
3OCH
3N
H SOCH(CH
3)
2H OCH
3CH
3N
H SOCH(CH
3)
2H OCH
2CH
3NHCH
3N
H SOCH(CH
3)
2CH
3OCH
3CH
3N
5-CH
3SOCH(CH
3)
2H OCH
3OCH
3CH
5-OCH
3SOCH(CH
3)
2H OCH
3OCH
3CH
6-CH
3SOCH(CH
3)
2H OCH
3OCH
3CH
6-OCH
3SOCH(CH
3)
2H OCH
3OCH
3CH
6-F SOCH(CH
3)
2H OCH
3OCH
3CH
6-Cl SOCH(CH
3)
2H OCH
3OCH
3CH
H SO
2CH(CH
3)
2H OCH
3OCH
3CH
H SO
2CH(CH
3)
2H OCH
3CH
3CH
H SO
2CH(CH
3)
2H Cl OCH
3CH
H SO
2CH(CH
3)
2H CH
3CH
3CH
H SO
2CH(CH
3)
2H OCH
3OCH
3N
H SO
2CH(CH
3)
2H OCH
3CH
3N
H SO
2CH(CH
3)
2H OCH
2CH
3NHCH
3N
H SO
2CH(CH
3)
2CH
3OCH
3CH
3N
5-CH
3SO
2CH(CH
3)
2H OCH
3OCH
3CH
5-OCH
3SO
2CH(CH
3)
2H OCH
3OCH
3CH
6-CH
3SO
2CH(CH
3)
2H OCH
3OCH
3CH
6-OCH
3SO
2CH(CH
3)
2H OCH
3OCH
3CH
6-F SO
2CH(CH
3)
2H OCH
3OCH
3CH
6-Cl SO
2CH(CH
3)
2H OCH
3OCH
3CH
Table IV (continuing)
R
fR
5R X Y Z m.p.(℃)
H S-cyclopropyl H OCH
3OCH
3CH
H S-cyclopropyl H OCH
3CH
3CH
H S-cyclopropyl H Cl OCH
3CH
H S-cyclopropyl H CH
3CH
3CH
H S-cyclopropyl H OCH
3OCH
3N
H S-cyclopropyl H OCH
3CH
3N
H S-cyclopropyl H OCH
2CH
3NHCH
3N
H S-cyclopropyl CH
3OCH
3CH
3N
5-CH
3S-cyclopropyl H OCH
3OCH
3CH
5-OCH
3S-cyclopropyl H OCH
3OCH
3CH
6-CH
3S-cyclopropyl H OCH
3OCH
3CH
6-OCH
3S-cyclopropyl H OCH
3OCH
3CH
6-F S-cyclopropyl H OCH
3OCH
3CH
6-Cl S-cyclopropyl H OCH
3OCH
3CH
H SO-cyclopropyl H OCH
3OCH
3CH
H SO-cyclopropyl H OCH
3CH
3CH
H SO-cyclopropyl H Cl OCH
3CH
H SO-cyclopropyl H CH
3CH
3CH
H SO-cyclopropyl H OCH
3OCH
3N
H SO-cyclopropyl H OCH
3CH
3N
H SO-cyclopropyl H OCH
2CH
3NHCH
3N
H SO-cyclopropyl CH
3OCH
3CH
3N
5-CH
3SO-cyclopropyl H OCH
3OCH
3CH
5-OCH
3SO-cyclopropyl H OCH
3OCH
3CH
6-CH
3SO-cyclopropyl H OCH
3OCH
3CH
6-OCH
3SO-cyclopropyl H OCH
3OCH
3CH
6-F SO-cyclopropyl H OCH
3OCH
3CH
6-Cl SO-cyclopropyl H OCH
3OCH
3CH
Table IV (continuing)
R
fR
5R X Y Z m.p.(℃)
H SO
2-cyclopropyl H OCH
3OCH
3CH
H SO
2-cyclopropyl H OCH
3CH
3CH
H SO
2-cyclopropyl H Cl OCH
3CH
H SO
2-cyclopropyl H CH
3CH
3CH
H SO
2-cyclopropyl H OCH
3OCH
3N
H SO
2-cyclopropyl H OCH
3CH
3N
H SO
2-cyclopropyl H OCH
2CH
3NHCH
3N
H SO
2-cyclopropyl CH
3OCH
3CH
3N
5-CH
3SO
2-cyclopropyl H OCH
3OCH
3CH
5-OCH
3SO
2-cyclopropyl H OCH
3OCH
3CH
6-CH
3SO
2-cyclopropyl H OCH
3OCH
3CH
6-OCH
3SO
2-cyclopropyl H OCH
3OCH
3CH
6-F SO
2-cyclopropyl H OCH
3OCH
3CH
6-Cl SO
2-cyclopropyl H OCH
3OCH
3CH
Table IV (continuing)
R
fR
5R X Y Z m.p.(℃)
H OSO
2CH
3H OCH
3OCH
3CH
H OSO
2CH
3H OCH
3CH
3CH
H OSO
2CH
3H Cl OCH
3CH
H OSO
2CH
3H CH
3CH
3CH
H OSO
2CH
3H OCH
3OCH
3N
H OSO
2CH
3H OCH
3CH
3N
H OSO
2CH
3H OCH
2CH
3NHCH
3N
H OSO
2CH
3CH
3OCH
3CH
3N
5-CH
3OSO
2CH
3H OCH
3OCH
3CH
5-OCH
3OSO
2CH
3H OCH
3OCH
3CH
6-CH
3OSO
2CH
3H OCH
3OCH
3CH
6-OCH
3OSO
2CH
3H OCH
3OCH
3CH
6-F OSO
2CH
3H OCH
3OCH
3CH
6-Cl OSO
2CH
3H OCH
3OCH
3CH
H OSO
2CF
3H OCH
3OCH
3CH
H OSO
2CF
3H OCH
3CH
3CH
H OSO
2CF
3H Cl OCH
3CH
H OSO
2CF
3H CH
3CH
3CH
H OSO
2CF
3H OCH
3OCH
3N
H OSO
2CF
3H OCH
3CH
3N
H OSO
2CF
3H OCH
2CH
3NHCH
3N
H OSO
2CF
3CH
3OCH
3CH
3N
5-CH
3OSO
2CF
3H OCH
3OCH
3CH
5-OCH
3OSO
2CF
3H OCH
3OCH
3CH
6-CH
3OSO
2CF
3H OCH
3OCH
3CH
6-OCH
3OSO
2CF
3H OCH
3OCH
3CH
6-F OSO
2CF
3H OCH
3OCH
3CH
6-Cl OSO
2CF
3H OCH
3OCH
3CH
Table IV (continuing)
R
fR
5R X Y Z m.p.(℃)
H OSO
2CH
2CH
3H OCH
3OCH
3CH
H OSO
2CH
2CH
3H OCH
3CH
3CH
H OSO
2CH
2CH
3H Cl OCH
3CH
H OSO
2CH
2CH
3H CH
3CH
3CH
H OSO
2CH
2CH
3H OCH
3OCH
3N
H OSO
2CH
2CH
3H OCH
3CH
3N
H OSO
2CH
2CH
3H OCH
2CH
3NHCH
3N
H OSO
2CH
2CH
3CH
3OCH
3CH
3N
5-CH
3OSO
2CH
2CH
3H OCH
3OCH
3CH
5-OCH
3OSO
2CH
2CH
3H OCH
3OCH
3CH
6-CH
3OSO
2CH
2CH
3H OCH
3OCH
3CH
6-OCH
3OSO
2CH
2CH
3H OCH
3OCH
3CH
6-F OSO
2CH
2CH
3H OCH
3OCH
3CH
6-Cl OSO
2CH
2CH
3H OCH
3OCH
3CH
H N
3H OCH
3OCH
3CH
H N
3H OCH
3CH
3CH
H N
3H Cl OCH
3CH
H N
3H CH
3CH
3CH
H N
3H OCH
3OCH
3N
H N
3H OCH
3CH
3N
H N
3H OCH
2CH
3NHCH
3N
H N
3CH
3OCH
3CH
3N
5-CH
3N
3H OCH
3OCH
3CH
5-OCH
3N
3H OCH
3OCH
3CH
6-CH
3N
3H OCH
3OCH
3CH
6-OCH
3N
3H OCH
3OCH
3CH
6-F N
3H OCH
3OCH
3CH
6-Cl N
3H OCH
3OCH
3CH
Table IV (continuing)
R
fR
5R X Y Z m.p.(℃)
H CN H OCH
3OCH
3CH
H CN H OCH
3CH
3CH
H CN H Cl OCH
3CH
H CN H CH
3CH
3CH
H CN H OCH
3OCH
3N
H CN H OCH
3CH
3N
H CN H OCH
2CH
3NHCH
3N
H CN CH
3OCH
3CH
3N
5-CH
3CN H OCH
3OCH
3CH
5-OCH
3CN H OCH
3OCH
3CH
6-CH
3CN H OCH
3OCH
3CH
6-OCH
3CN H OCH
3OCH
3CH
6-F CN H OCH
3OCH
3CH
6-Cl CN H OCH
3OCH
3CH
Table IV (continuing)
R
fR
5R X Y Z m.p.(℃)
H CH
2F H OCH
3OCH
3CH
H CH
2F H OCH
3CH
3CH
H CH
2F H Cl OCH
3CH
H CH
2F H CH
3CH
3CH
H CH
2F H OCH
3OCH
3N
H CH
2F H OCH
3CH
3N
H CH
2F H OCH
2CH
3NHCH
3N
H CH
2F CH
3OCH
3CH
3N
5-CH
3CH
2F H OCH
3OCH
3CH
5-OCH
3CH
2F H OCH
3OCH
3CH
6-CH
3CH
2F H OCH
3OCH
3CH
6-OCH
3CH
2F H OCH
3OCH
3CH
6-F CH
2F H OCH
3OCH
3CH
6-Cl CH
2F H OCH
3OCH
3CH
H CF
2H H OCH
3OCH
3CH
H CF
2H H OCH
3CH
3CH
H CF
2H H Cl OCH
3CH
H CF
2H H CH
3CH
3CH
H CF
2H H OCH
3OCH
3N
H CF
2H H OCH
3CH
3N
H CF
2H H OCH
2CH
3NHCH
3N
H CF
2H CH
3OCH
3CH
3N
5-CH
3CF
2H H OCH
3OCH
3CH
5-OCH
3CF
2H H OCH
3OCH
3CH
6-CH
3CF
2H H OCH
3OCH
3CH
6-OCH
3CF
2H H OCH
3OCH
3CH
6-F CF
2H H OCH
3OCH
3CH
6-Cl CF
2H H OCH
3OCH
3CH
Table IV (continuing)
R
fR
5R X Y Z m.p.(℃)
H SO
2N(OCH
3)CH
3H OCH
3OCH
3CH
H SO
2N(OCH
3)CH
3H OCH
3CH
3CH
H SO
2N(OCH
3)CH
3H Cl OCH
3CH
H SO
2N(OCH
3)CH
3H CH
3CH
3CH
H SO
2N(OCH
3)CH
3H OCH
3OCH
3N
H SO
2N(OCH
3)CH
3H OCH
3CH
3N
H SO
2N(OCH
3)CH
3H OCH
2CH
3NHCH
3N
H SO
2N(OCH
3)CH
3CH
3OCH
3CH
3N
5-CH
3SO
2N(OCH
3)CH
3H OCH
3OCH
3CH
5-OCH
3SO
2N(OCH
3)CH
3H OCH
3OCH
3CH
6-CH
3SO
2N(OCH
3)CH
3H OCH
3OCH
3CH
6-OCH
3SO
2N(OCH
3)CH
3H OCH
3OCH
3CH
6-F SO
2N(OCH
3)CH
3H OCH
3OCH
3CH
6-Cl SO
2N(OCH
3)CH
3H OCH
3OCH
3CH
H SO
2NHCH
3H OCH
3OCH
3CH
H SO
2NHCH
3H OCH
3CH
3CH
H SO
2NHCH
3H Cl OCH
3CH
H SO
2NHCH
3H CH
3CH
3CH
H SO
2NHCH
3H OCH
3OCH
3N
H SO
2NHCH
3H OCH
3CH
3N
H SO
2NHCH
3H OCH
2CH
3NHCH
3N
H SO
2NHCH
3CH
3OCH
3CH
3N
5-CH
3SO
2NHCH
3H OCH
3OCH
3CH
5-OCH
3SO
2NHCH
3H OCH
3OCH
3CH
6-CH
3SO
2NHCH
3H OCH
3OCH
3CH
6-OCH
3SO
2NHCH
3H OCH
3OCH
3CH
6-F SO
2NHCH
3H OCH
3OCH
3CH
6-Cl SO
2NHCH
3H OCH
3OCH
3CH
Table IV (continuing)
R
fR
5R X Y Z m.p.(℃)
H SO
2NHCH
2CH
3H OCH
3OCH
3CH
H SO
2NHCH
2CH
3H OCH
3CH
3CH
H SO
2NHCH
2CH
3H Cl OCH
3CH
H SO
2NHCH
2CH
3H CH
3CH
3CH
H SO
2NHCH
2CH
3H OCH
3OCH
3N
H SO
2NHCH
2CH
3H OCH
3CH
3N
H SO
2NHCH
2CH
3H OCH
2CH
3NHCH
3N
H SO
2NHCH
2CH
3CH
3OCH
3CH
3N
5-CH
3SO
2NHCH
2CH
3H OCH
3OCH
3CH
5-OCH
3SO
2NHCH
2CH
3H OCH
3OCH
3CH
6-CH
3SO
2NHCH
2CH
3H OCH
3OCH
3CH
6-OCH
3SO
2NHCH
2CH
3H OCH
3OCH
3CH
6-F SO
2NHCH
2CH
3H OCH
3OCH
3CH
6-Cl SO
2NHCH
2CH
3H OCH
3OCH
3CH
H CO
2CH
2CH
2OH H OCH
3OCH
3CH
H CO
2CH
2CH
2OH H OCH
3CH
3CH
H CO
2CH
2CH
2OH H Cl OCH
3CH
H CO
2CH
2CH
2OH H CH
3CH
3CH
H CO
2CH
2CH
2OH H OCH
3OCH
3N
H CO
2CH
2CH
2OH H OCH
3CH
3N
H CO
2CH
2CH
2OH H OCH
2CH
3NHCH
3N
H CO
2CH
2CH
2OH CH
3OCH
3CH
3N
5-CH
3CO
2CH
2CH
2OH H OCH
3OCH
3CH
5-OCH
3CO
2CH
2CH
2OH H OCH
3OCH
3CH
6-CH
3CO
2CH
2CH
2OH H OCH
3OCH
3CH
6-OCH
3CO
2CH
2CH
2OH H OCH
3OCH
3CH
6-F CO
2CH
2CH
2OH H OCH
3OCH
3CH
6-Cl CO
2CH
2CH
2OH H OCH
3OCH
3CH
H CO
2CH
2CH
2CN H OCH
3OCH
3CH
H CO
2CH
2CH
2CN H OCH
3CH
3CH
H CO
2CH
2CH
2CN H Cl OCH
3CH
Table IV (continuing)
R
fR
5R X Y Z m.p.(℃)
H CO
2CH
2CH
2CN H CH
3CH
3CH
H CO
2CH
2CH
2CN H OCH
3OCH
3N
H CO
2CH
2CH
2CN H OCH
3CH
3N
H CO
2CH
2CH
2CN H OCH
2CH
3NHCH
3N
H CO
2CH
2CH
2CN CH
3OCH
3CH
3N
5-CH
3CO
2CH
2CH
2CN H OCH
3OCH
3CH
5-OCH
3CO
2CH
2CH
2CN H OCH
3OCH
3CH
6-CH
3CO
2CH
2CH
2CN H OCH
3OCH
3CH
6-OCH
3CO
2CH
2CH
2CN H OCH
3OCH
3CH
6-F CO
2CH
2CH
2CN H OCH
3OCH
3CH
6-Cl CO
2CH
2CH
2CN H OCH
3OCH
3CH
H CO
2CH
2CH
2OSO
2CH
3H OCH
3OCH
3CH
H CO
2CH
2CH
2OSO
2CH
3H OCH
3CH
3CH
H CO
2CH
2CH
2OSO
2CH
3H Cl OCH
3CH
H CO
2CH
2CH
2OSO
2CH
3H CH
3CH
3CH
H CO
2CH
2CH
2OSO
2CH
3H OCH
3OCH
3N
H CO
2CH
2CH
2OSO
2CH
3H OCH
3CH
3N
H CO
2CH
2CH
2OSO
2CH
3H OCH
2CH
3NHCH
3N
H CO
2CH
2CH
2OSO
2CH
3CH
3OCH
3CH
3N
5-CH
3CO
2CH
2CH
2OSO
2CH
3H OCH
3OCH
3CH
5-OCH
3CO
2CH
2CH
2OSO
2CH
3H OCH
3OCH
3CH
6-CH
3CO
2CH
2CH
2OSO
2CH
3H OCH
3OCH
3CH
6-OCH
3CO
2CH
2CH
2OSO
2CH
3H OCH
3OCH
3CH
6-F CO
2CH
2CH
2OSO
2CH
3H OCH
3OCH
3CH
6-Cl CO
2CH
2CH
2OSO
2CH
3H OCH
3OCH
3CH
The table V
General formula 5
R
fR
6R X Y Z m.p.(℃)
H SCH
3H OCH
3OCH
3CH
H SCH
3H OCH
3CH
3CH
H SCH
3H Cl OCH
3CH
H SCH
3H CH
3CH
3CH
H SCH
3H OCH
3OCH
3N
H SCH
3H OCH
3CH
3N
H SCH
3H OCH
2CH
3NHCH
3N
H SCH
3CH
3OCH
3CH
3N
4-CH
3SCH
3H OCH
3OCH
3CH
4-OCH
3SCH
3H OCH
3OCH
3CH
6-CH
3SCH
3H OCH
3OCH
3CH
6-OCH
3SCH
3H OCH
3OCH
3CH
6-F SCH
3H OCH
3OCH
3CH
6-Cl SCH
3H OCH
3OCH
3CH
H SOCH
3H OCH
3OCH
3CH
H SOCH
3H OCH
3CH
3CH
H SOCH
3H Cl OCH
3CH
H SOCH
3H CH
3CH
3CH
H SOCH
3H OCH
3OCH
3N
H SOCH
3H OCH
3CH
3N
H SOCH
3H OCH
2CH
3NHCH
3N
H SOCH
3CH
3OCH
3CH
3N
4-CH
3SOCH
3H OCH
3OCH
3CH
4-OCH
3SOCH
3H OCH
3OCH
3CH
6-CH
3SOCH
3H OCH
3OCH
3CH
6-OCH
3SOCH
3H OCH
3OCH
3CH
6-F SOCH
3H OCH
3OCH
3CH
6-Cl SOCH
3H OCH
3OCH
3CH
Table V (continuing)
R
fR
6R X Y Z m.p.(℃)
H SO-cyclopropyl H OCH
3OCH
3CH
H SO-cyclopropyl H OCH
3CH
3CH
H SO-cyclopropyl H Cl OCH
3CH
H SO-cyclopropyl H CH
3CH
3CH
H SO-cyclopropyl H OCH
3OCH
3N
H SO-cyclopropyl H OCH
3CH
3N
H SO-cyclopropyl H OCH
2CH
3NHCH
3N
H SO-cyclopropyl CH
3OCH
3CH
3N
4-CH
3SO-cyclopropyl H OCH
3OCH
3CH
4-OCH
3SO-cyclopropyl H OCH
3OCH
3CH
6-CH
3SO-cyclopropyl H OCH
3OCH
3CH
6-OCH
3SO-cyclopropyl H OCH
3OCH
3CH
6-F SO-cyclopropyl H OCH
3OCH
3CH
6-Cl SO-cyclopropyl H OCH
3OCH
3CH
H SO
2-cyclopropyl H OCH
3OCH
3CH
H SO
2-cyclopropyl H OCH
3CH
3CH
H SO
2-cyclopropyl H Cl OCH
3CH
H SO
2-cyclopropyl H CH
3CH
3CH
H SO
2-cyclopropyl H OCH
3OCH
3N
H SO
2-cyclopropyl H OCH
3CH
3N
H SO
2-cyclopropyl H OCH
2CH
3NHCH
3N
H SO
2-cyclopropyl CH
3OCH
3CH
3N
4-CH
3SO
2-cyclopropyl H OCH
3OCH
3CH
4-OCH
3SO
2-cyclopropyl H OCH
3OCH
3CH
6-CH
3SO
2-cyclopropyl H OCH
3OCH
3CH
6-OCH
3SO
2-cyclopropyl H OCH
3OCH
3CH
6-F SO
2-cyclopropyl H OCH
3OCH
3CH
6-Cl SO
2-cyclopropyl H OCH
3OCH
3CH
Table V (continuing)
R
fR
6R X Y Z m.p.(℃)
H OSO
2CH
3H OCH
3OCH
3CH
H OSO
2CH
3H OCH
3CH
3CH
H OSO
2CH
3H Cl OCH
3CH
H OSO
2CH
3H CH
3CH
3CH
H OSO
2CH
3H OCH
3OCH
3N
H OSO
2CH
3H OCH
3CH
3N
H OSO
2CH
3H OCH
2CH
3NHCH
3N
H OSO
2CH
3CH
3OCH
3CH
3N
4-CH
3OSO
2CH
3H OCH
3OCH
3CH
4-OCH
3OSO
2CH
3H OCH
3OCH
3CH
6-CH
3OSO
2CH
3H OCH
3OCH
3CH
6-OCH
3OSO
2CH
3H OCH
3OCH
3CH
6-F OSO
2CH
3H OCH
3OCH
3CH
6-Cl OSO
2CH
3H OCH
3OCH
3CH
H CN H OCH
3OCH
3CH
H CN H OCH
3CH
3CH
H CN H Cl OCH
3CH
H CN H CH
3CH
3CH
H CN H OCH
3OCH
3N
H CN H OCH
3CH
3N
H CN H OCH
2CH
3NHCH
3N
H CN CH
3OCH
3CH
3N
4-CH
3CN H OCH
3OCH
3CH
4-OCH
3CN H OCH
3OCH
3CH
6-CH
3CN H OCH
3OCH
3CH
6-OCH
3CN H OCH
3OCH
3CH
6-F CN H OCH
3OCH
3CH
6-Cl CN H OCH
3OCH
3CH
Table V (continuing)
R
fR
6R X Y Z m.p.(℃)
H CH
2F H OCH
3OCH
3CH
H CH
2F H OCH
3CH
3CH
H CH
2F H Cl OCH
3CH
H CH
2F H CH
3CH
3CH
H CH
2F H OCH
3OCH
3N
H CH
2F H OCH
3CH
3N
H CH
2F H OCH
2CH
3NHCH
3N
H CH
2F CH
3OCH
3CH
3N
4-CH
3CH
2F H OCH
3OCH
3CH
4-OCH
3CH
2F H OCH
3OCH
3CH
6-CH
3CH
2F H OCH
3OCH
3CH
6-OCH
3CH
2F H OCH
3OCH
3CH
6-F CH
2F H OCH
3OCH
3CH
6-Cl CH
2F H OCH
3OCH
3CH
Table V (continuing)
R
fR
6R X Y Z m.p.(℃)
H SO
2N(OCH
3)CH
3H OCH
3OCH
3CH
H SO
2N(OCH
3)CH
3H OCH
3CH
3CH
H SO
2N(OCH
3)CH
3H Cl OCH
3CH
H SO
2N(OCH
3)CH
3H CH
3CH
3CH
H SO
2N(OCH
3)CH
3H OCH
3OCH
3N
H SO
2N(OCH
3)CH
3H OCH
3CH
3N
H SO
2N(OCH
3)CH
3H OCH
2CH
3NHCH
3N
H SO
2N(OCH
3)CH
3CH
3OCH
3CH
3N
4-CH
3SO
2N(OCH
3)CH
3H OCH
3OCH
3CH
4-OCH
3SO
2N(OCH
3)CH
3H OCH
3OCH
3CH
6-CH
3SO
2N(OCH
3)CH
3H OCH
3OCH
3CH
6-OCH
3SO
2N(OCH
3)CH
3H OCH
3OCH
3CH
6-F SO
2N(OCH
3)CH
3H OCH
3OCH
3CH
6-Cl SO
2N(OCH
3)CH
3H OCH
3OCH
3CH
H CO
2CH
2CH
2OH H OCH
3OCH
3CH
H CO
2CH
2CH
2OH H OCH
3CH
3CH
H CO
2CH
2CH
2OH H Cl OCH
3CH
H CO
2CH
2CH
2OH H CH
3CH
3CH
H CO
2CH
2CH
2OH H OCH
3OCH
3N
H CO
2CH
2CH
2OH H OCH
3CH
3N
H CO
2CH
2CH
2OH H OCH
2CH
3NHCH
3N
H CO
2CH
2CH
2OH CH
3OCH
3CH
3N
4-CH
3CO
2CH
2CH
2OH H OCH
3OCH
3CH
4-OCH
3CO
2CH
2CH
2OH H OCH
3OCH
3CH
6-CH
3CO
2CH
2CH
2OH H OCH
3OCH
3CH
6-OCH
3CO
2CH
2CH
2OH H OCH
3OCH
3CH
6-F CO
2CH
2CH
2OH H OCH
3OCH
3CH
Table V (continuing)
R
fR
6R X Y Z m.p.(℃)
6-Cl CO
2CH
2CH
2OH H OCH
3OCH
3CH
H CO
2CH
2CH
2CN H OCH
3OCH
3CH
H CO
2CH
2CH
2CN H OCH
3CH
3CH
H CO
2CH
2CH
2CN H Cl OCH
3CH
H CO
2CH
2CH
2CN H CH
3CH
3CH
H CO
2CH
2CH
2CN H OCH
3OCH
3N
H CO
2CH
2CH
2CN H OCH
3CH
3N
H CO
2CH
2CH
2CN H OCH
2CH
3NHCH
3N
H CO
2CH
2CH
2CN CH
3OCH
3CH
3N
4-CH
3CO
2CH
2CH
2CN H OCH
3OCH
3CH
4-OCH
3CO
2CH
2CH
2CN H OCH
3OCH
3CH
6-CH
3CO
2CH
2CH
2CN H OCH
3OCH
3CH
6-OCH
3CO
2CH
2CH
2CN H OCH
3OCH
3CH
6-F CO
2CH
2CH
2CN H OCH
3OCH
3CH
6-Cl CO
2CH
2CH
2CN H OCH
3OCH
3CH
H CO
2CH
2CF
3H OCH
3OCH
3CH
H CO
2CH
2CF
3H OCH
3CH
3CH
H CO
2CH
2CF
3H Cl OCH
3CH
H CO
2CH
2CF
3H CH
3CH
3CH
H CO
2CH
2CF
3H OCH
3OCH
3N
H CO
2CH
2CF
3H OCH
3CH
3N
H CO
2CH
2CF
3H OCH
2CH
3NHCH
3N
H CO
2CH
2CF
3CH
3OCH
3CH
3N
4-CH
3CO
2CH
2CF
3H OCH
3OCH
3CH
4-OCH
3CO
2CH
2CF
3H OCH
3OCH
3CH
6-CH
3CO
2CH
2CF
3H OCH
3OCH
3CH
6-OCH
3CO
2CH
2CF
3H OCH
3OCH
3CH
6-F CO
2CH
2CF
3H OCH
3OCH
3CH
6-Cl CO
2CH
2CF
3H OCH
3OCH
3CH
The table VI
General formula 6
R
fR
6R X Y Z m.p.(℃)
H SCH
3H OCH
3OCH
3CH
H SCH
3H OCH
3CH
3CH
H SCH
3H Cl OCH
3CH
H SCH
3H CH
3CH
3CH
H SCH
3H OCH
3OCH
3N
H SCH
3H OCH
3CH
3N
H SCH
3H OCH
2CH
3NHCH
3N
H SCH
3CH
3OCH
3CH
3N
4-CH
3SCH
3H OCH
3OCH
3CH
4-Cl SCH
3H OCH
3OCH
3CH
6-CH
3SCH
3H OCH
3OCH
3CH
6-OCH
3SCH
3H OCH
3OCH
3CH
6-F SCH
3H OCH
3OCH
3CH
6-Cl SCH
3H OCH
3OCH
3CH
H SOCH
3H OCH
3OCH
3CH
H SOCH
3H OCH
3CH
3CH
H SOCH
3H Cl OCH
3CH
H SOCH
3H CH
3CH
3CH
H SOCH
3H OCH
3OCH
3N
H SOCH
3H OCH
3CH
3N
H SOCH
3H OCH
2CH
3NHCH
3N
H SOCH
3CH
3OCH
3CH
3N
4-CH
3SOCH
3H OCH
3OCH
3CH
4-Cl SOCH
3H OCH
3OCH
3CH
6-CH
3SOCH
3H OCH
3OCH
3CH
6-OCH
3SOCH
3H OCH
3OCH
3CH
6-F SOCH
3H OCH
3OCH
3CH
6-Cl SOCH
3H OCH
3OCH
3CH
Table VI (continuing)
m.p.
R
fR
6R X Y Z (℃)
H SO-cyclopropyl H OCH
3OCH
3CH
H SO-cyclopropyl H OCH
3CH
3CH
H SO-cyclopropyl H Cl OCH
3CH
H SO-cyclopropyl H CH
3CH
3CH
H SO-cyclopropyl H OCH
3OCH
3N
H SO-cyclopropyl H OCH
3CH
3N
H SO-cyclopropyl H OCH
2CH
3NHCH
3N
H SO-cyclopropyl CH
3OCH
3CH
3N
4-CH
3SO-cyclopropyl H OCH
3OCH
3CH
4-Cl SO-cyclopropyl H OCH
3OCH
3CH
6-CH
3SO-cyclopropyl H OCH
3OCH
3CH
6-OCH
3SO-cyclopropyl H OCH
3OCH
3CH
6-F SO-cyclopropyl H OCH
3OCH
3CH
6-Cl SO-cyclopropyl H OCH
3OCH
3CH
H SO
2-cyclopropyl H OCH
3OCH
3CH
H SO
2-cyclopropyl H OCH
3CH
3CH
H SO
2-cyclopropyl H Cl OCH
3CH
H SO
2-cyclopropyl H CH
3CH
3CH
H SO
2-cyclopropyl H OCH
3OCH
3N
H SO
2-cyclopropyl H OCH
3CH
3N
H SO
2-cyclopropyl H OCH
2CH
3NHCH
3N
H SO
2-cyclopropyl CH
3OCH
3CH
3N
4-CH
3SO
2-cyclopropyl H OCH
3OCH
3CH
4-Cl SO
2-cyclopropyl H OCH
3OCH
3CH
6-CH
3SO
2-cyclopropyl H OCH
3OCH
3CH
6-OCH
3SO
2-cyclopropyl H OCH
3OCH
3CH
6-F SO
2-cyclopropyl H OCH
3OCH
3CH
6-Cl SO
2-cyclopropyl H OCH
3OCH
3CH
Table VI (continuing)
m.p.
R
fR
6R X Y Z (℃)
H OSO
2CH
3H OCH
3OCH
3CH
H OSO
2CH
3H OCH
3CH
3CH
H OSO
2CH
3H Cl OCH
3CH
H OSO
2CH
3H CH
3CH
3CH
H OSO
2CH
3H OCH
3OCH
3N
H OSO
2CH
3H OCH
3CH
3N
H OSO
2CH
3H OCH
2CH
3NHCH
3N
H OSO
2CH
3CH
3OCH
3CH
3N
4-CH
3OSO
2CH
3H OCH
3OCH
3CH
4-Cl OSO
2CH
3H OCH
3OCH
3CH
6-CH
3OSO
2CH
3H OCH
3OCH
3CH
6-OCH
3OSO
2CH
3H OCH
3OCH
3CH
6-F OSO
2CH
3H OCH
3OCH
3CH
6-Cl OSO
2CH
3H OCH
3OCH
3CH
Table VI (continuing)
m.p.
R
fR
6R X Y Z (℃)
H CN H OCH
3OCH
3CH
H CN H OCH
3CH
3CH
H CN H Cl OCH
3CH
H CN H CH
3CH
3CH
H CN H OCH
3OCH
3N
H CN H OCH
3CH
3N
H CN H OCH
2CH
3NHCH
3N
H CN CH
3OCH
3CH
3N
4-CH
3CN H OCH
3OCH
3CH
4-Cl CN H OCH
3OCH
3CH
6-CH
3CN H OCH
3OCH
3CH
6-OCH
3CN H OCH
3OCH
3CH
6-F CN H OCH
3OCH
3CH
6-Cl CN H OCH
3OCH
3CH
Table VI (continuing)
R
fR
6R X Y Z m.p.(℃)
H SO
2N(OCH
3)CH
3H OCH
3OCH
3CH
H SO
2N(OCH
3)CH
3H OCH
3CH
3CH
H SO
2N(OCH
3)CH
3H Cl OCH
3CH
H SO
2N(OCH
3)CH
3H CH
3CH
3CH
H SO
2N(OCH
3)CH
3H OCH
3OCH
3N
H SO
2N(OCH
3)CH
3H OCH
3CH
3N
H SO
2N(OCH
3)CH
3H OCH
2CH
3NHCH
3N
H SO
2N(OCH
3)CH
3CH
3OCH
3CH
3N
4-CH
3SO
2N(OCH
3)CH
3H OCH
3OCH
3CH
4-Cl SO
2N(OCH
3)CH
3H OCH
3OCH
3CH
6-CH
3SO
2N(OCH
3)CH
3H OCH
3OCH
3CH
6-OCH
3SO
2N(OCH
3)CH
3H OCH
3OCH
3CH
6-F SO
2N(OCH
3)CH
3H OCH
3OCH
3CH
6-Cl SO
2N(OCH
3)CH
3H OCH
3OCH
3CH
H CO
2CH
2CH
2OH H OCH
3OCH
3CH
H CO
2CH
2CH
2OH H OCH
3CH
3CH
H CO
2CH
2CH
2OH H Cl OCH
3CH
H CO
2CH
2CH
2OH H CH
3CH
3CH
H CO
2CH
2CH
2OH H OCH
3OCH
3N
H CO
2CH
2CH
2OH H OCH
3CH
3N
H CO
2CH
2CH
2OH H OCH
2CH
3NHCH
3N
H CO
2CH
2CH
2OH CH
3OCH
3CH
3N
4-CH
3CO
2CH
2CH
2OH H OCH
3OCH
3CH
4-Cl CO
2CH
2CH
2OH H OCH
3OCH
3CH
6-CH
3CO
2CH
2CH
2OH H OCH
3OCH
3CH
6-OCH
3CO
2CH
2CH
2OH H OCH
3OCH
3CH
6-F CO
2CH
2CH
2OH H OCH
3OCH
3CH
6-Cl CO
2CH
2CH
2OH H OCH
3OCH
3CH
H CO
2CH
2CH
2CN H OCH
3OCH
3CH
Table VI (continuing)
R
fR
6R X Y Z m.p.(℃)
H CO
2CH
2CH
2CN H OCH
3CH
3CH
H CO
2CH
2CH
2CN H Cl OCH
3CH
H CO
2CH
2CH
2CN H CH
3CH
3CH
H CO
2CH
2CH
2CN H OCH
3OCH
3N
H CO
2CH
2CH
2CN H OCH
3CH
3N
H CO
2CH
2CH
2CN H OCH
2CH
3NHCH
3N
H CO
2CH
2CH
2CN CH
3OCH
3CH
3N
4-CH
3CO
2CH
2CH
2CN H OCH
3OCH
3CH
4-Cl CO
2CH
2CH
2CN H OCH
3OCH
3CH
6-CH
3CO
2CH
2CH
2CN H OCH
3OCH
3CH
6-OCH
3CO
2CH
2CH
2CN H OCH
3OCH
3CH
6-F CO
2CH
2CH
2CN H OCH
3OCH
3CH
6-Cl CO
2CH
2CH
2CN H OCH
3OCH
3CH
The table VII
General formula 7
R
1R
2A X Y m.p.(℃)
H SOCH
3A-2 X
1=CH
3Y
1=CH
2
H SOCH
3A-3 X
1=CH
3
H SOCH
3A-3 X
1=OCH
3
H SOCH
3A-4 X
3=OCH
3
H SO
2CH
3A-2 X
1=CH
3Y
1=CH
2
H SO
2CH
3A-3 X
1=CH
3
H SO
2CH
3A-3 X
1=OCH
3
H SO
2CH
3A-4 X
3=OCH
3
H SOCH
2CH
3A-2 X
1=CH
3Y
1=CH
2
H SOCH
2CH
3A-3 X
1=CH
3
H SOCH
2CH
3A-3 X
1=OCH
3
H SOCH
2CH
3A-4 X
3=OCH
3
H SO
2CH
2CH
3A-2 X
1=CH
3Y
1=CH
2
H SO
2CH
2CH
3A-3 X
1=CH
3
H SO
2CH
2CH
3A-3 X
1=OCH
3
H SO
2CH
2CH
3A-4 X
3=OCH
3
H SOCH
2CH
2CH
3A-2 X
1=CH
3Y
1=CH
2
H SOCH
2CH
2CH
3A-3 X
1=CH
3
H SOCH
2CH
2CH
3A-3 X
1=OCH
3
H SOCH
2CH
2CH
3A-4 X
3=OCH
3
H SO
2CH
2CH
2CH
3A-2 X
1=CH
3Y
1=CH
2
H SO
2CH
2CH
2CH
3A-3 X
1=CH
3
H SO
2CH
2CH
2CH
3A-3 X
1=OCH
3
H SO
2CH
2CH
2CH
3A-4 X
3=OCH
3
H SOCH(CH
3)
2A-2 X
1=CH
3Y
1=CH
2
H SOCH(CH
3)
2A-3 X
1=CH
3
H SOCH(CH
3)
2A-3 X
1=OCH
3
H SOCH(CH
3)
2A-4 X
3=OCH
3
H SO
2CH(CH
3)
2A-2 X
1=CH
3Y
1=CH
2
H SO
2CH(CH
3)
2A-3 X
1=CH
3
H SO
2CH(CH
3)
2A-3 X
1=OCH
3
Table VII (continuing)
R
1R
2A X Y m.p.(℃)
H SO
2CH(CH
3)
2A-4 X
3=OCH
3
H SOCH
2CH
2CH
2CH
3A-2 X
1=CH
3Y
1=CH
2
H SOCH
2CH
2CH
2CH
3A-3 X
1=CH
3
H SOCH
2CH
2CH
2CH
3A-3 X
1=OCH
3
H SOCH
2CH
2CH
2CH
3A-4 X
3=OCH
3
H SO
2CH
2CH
2CH
2CH
3A-2 X
1=CH
3Y
1=CH
2
H SO
2CH
2CH
2CH
2CH
3A-3 X
1=CH
3
H SO
2CH
2CH
2CH
2CH
3A-3 X
1=OCH
3
H SO
2CH
2CH
2CH
2CH
3A-4 X
3=OCH
3
H S-cyclopropyl A-2 X
1=CH
3Y
1=CH
2
H S-cyclopropyl A-3 X
1=CH
3
H S-cyclopropyl A-3 X
1=OCH
3
H S-cyclopropyl A-4 X
3=OCH
3
H SO
2-cyclopropyl A-2 X
1=CH
3Y
1=CH
2
H SO
2-cyclopropyl A-3 X
1=CH
3
H SO
2-cyclopropyl A-3 X
1=OCH
3
H SO
2-cyclopropyl A-4 X
3=OCH
3
Table VII (continuing)
R
1R
2A X Y m.p.(℃)
H OSO
2CH
3A-2 X
1=CH
3Y
1=CH
2
H OSO
2CH
3A-3 X
1=CH
3
H OSO
2CH
3A-3 X
1=OCH
3
H OSO
2CH
3A-4 X
3=OCH
3
H OSO
2CH
3A-7 X
4=OCH
3Y
4=OCH
3
H OSO
2CH
2CH
3A-2 X
1=CH
3Y
1=CH
2
H OSO
2CH
2CH
3A-3 X
1=CH
3
H OSO
2CH
2CH
3A-3 X
1=OCH
3
H OSO
2CH
2CH
3A-4 X
3=OCH
3
H OSO
2CF
3A-2 X
1=CH
3Y
1=CH
2
H OSO
2CF
3A-3 X
1=CH
3
H OSO
2CF
3A-3 X
1=OCH
3
H OSO
2CF
3A-4 X
3=OCH
3
H OSO
2CCl
3A-2 X
1=CH
3Y
1=CH
2
H OSO
2CCl
3A-3 X
1=CH
3
H OSO
2CCl
3A-3 X
1=OCH
3
H OSO
2CCl
3A-4 X
3=OCH
3
H CN A-2 X
1=CH
3Y
1=CH
2
H CN A-3 X
1=CH
3
H CN A-3 X
1=OCH
3
H CN A-4 X
3=OCH
3
H CH
2F A-2 X
1=CH
3Y
1=CH
2
H CH
2F A-3 X
1=CH
3
H CH
2F A-3 X
1=OCH
3
H CH
2F A-4 X
3=OCH
3
H CF
2H A-2 X
1=CH
3Y
1=CH
2
H CF
2H A-3 X
1=CH
3
H CF
2H A-3 X
1=OCH
3
H CF
2H A-4 X
3=OCH
3
Table VII (continuing)
R
1R
2A X Y m.p.(℃)
H SO
2NHCH
3A-2 X
1=CH
3Y
1=CH
2
H SO
2NHCH
3A-3 X
1=CH
3
H SO
2NHCH
3A-3 X
1=OCH
3
H SO
2NHCH
3A-4 X
3=OCH
3
H SO
2NHCH
2CH
2OCH
3A-2 X
1=CH
3Y
1=CH
2
H SO
2NHCH
2CH
2OCH
3A-3 X
1=CH
3
H SO
2NHCH
2CH
2OCH
3A-3 X
1=OCH
3
H SO
2NHCH
2CH
2OCH
3A-4 X
3=OCH
3
H CO
2CH
2CH
2OH A-2 X
1=CH
3Y
1=CH
2
H CO
2CH
2CH
2OH A-3 X
1=CH
3
H CO
2CH
2CH
2OH A-3 X
1=OCH
3
H CO
2CH
2CH
2OH A-4 X
3=OCH
3
H CO
2CH
2CH
2CN A-2 X
1=CH
3Y
1=CH
2
H CO
2CH
2CH
2CN A-3 X
1=CH
3
H CO
2CH
2CH
2CN A-3 X
1=OCH
3
H CO
2CH
2CH
2CN A-4 X
3=OCH
3
H CO
2CH
2CF
2A-2 X
1=CH
3Y
1=CH
2
H CO
2CH
2CF
2A-3 X
1=CH
3
H CO
2CH
2CF
2A-3 X
1=OCH
3
6-OCH
3SO
2N(CH
3)
2A-2 X
1=CH
3Y
1=CH
2
6-OCH
3SO
2N(CH
3)
2A-3 X
1=CH
3
6-OCH
3SO
2N(CH
3)
2A-3 X
1=OCH
3
6-OCH
3SO
2N(CH
3)
2A-4 X
3=OCH
3
6-SCH
3SO
2N(CH
3)
2A-2 X
1=CH
3Y
1=CH
2
6-SCH
3SO
2N(CH
3)
2A-3 X
1=CH
3
6-SCH
3SO
2N(CH
3)
2A-3 X
1=OCH
3
6-SCH
3SO
2N(CH
3)
2A-4 X
3=OCH
3
Table VII (continuing)
R
1R
2A X Y m.p.(℃)
6-N(CH
3)
2SO
2N(CH
3)
2A-2 X
1=CH
3Y
1=CH
2
6-N(CH
3)
2SO
2N(CH
3)
2A-3 X
1=CH
3
6-N(CH
3)
2SO
2N(CH
3)
2A-3 X
1=OCH
3
6-N(CH
3)
2SO
2N(CH
3)
2A-4 X
3=OCH
3
6-NHCH
3SO
2N(CH
3)
2A-2 X
1=CH
3Y
1=CH
2
6-NHCH
3SO
2N(CH
3)
2A-3 X
1=CH
3
6-NHCH
3SO
2N(CH
3)
2A-3 X
1=OCH
3
6-NHCH
3SO
2N(CH
3)
2A-4 X
3=OCH
3
6-OCH
3CO
2CH
3A-2 X
1=CH
3Y
1=CH
2
6-OCH
3CO
2CH
3A-3 X
1=CH
3
6-OCH
3CO
2CH
3A-3 X
1=OCH
3
6-OCH
3CO
2CH
3A-4 X
3=OCH
3
6-SCH
3CO
2CH
3A-2 X
1=CH
3Y
1=CH
2
6-SCH
3CO
2CH
3A-3 X
1=CH
3
6-SCH
3CO
2CH
3A-3 X
1=OCH
3
6-SCH
3CO
2CH
3A-4 X
3=OCH
3
6-N(CH
3)
2CO
2CH
3A-2 X
1=CH
3Y
1=CH
2
6-N(CH
3)
2CO
2CH
3A-3 X
1=CH
3
6-N(CH
3)
2CO
2CH
3A-3 X
1=OCH
3
6-N(CH
3)
2CO
2CH
3A-4 X
3=OCH
3
Table VII (continuing)
R
1R
2A X Y m.p.(℃)
6-NHCH
3SO
2N(CH
3)
2A-2 X
1=CH
3Y
1=CH
2
6-NHCH
3SO
2N(CH
3)
2A-3 X
1=CH
3
6-NHCH
3SO
2N(CH
3)
2A-3 X
1=OCH
3
6-NHCH
3SO
2N(CH
3)
2A-4 X
3=OCH
3
6-OCH
3SO
2N(CH
3)
2A-2 X
1=CH
3Y
1=CH
2
6-OCH
3SO
2N(CH
3)
2A-3 X
1=CH
3
6-OCH
3SO
2N(CH
3)
2A-3 X
1=OCH
3
6-OCH
3SO
2N(CH
3)
2A-4 X
3=OCH
3
6-SCH
3SO
2N(CH
3)
2A-2 X
1=CH
3Y
1=CH
2
6-SCH
3SO
2N(CH
3)
2A-3 X
1=CH
3
6-SCH
3SO
2N(CH
3)
2A-3 X
1=OCH
3
6-SCH
3SO
2N(CH
3)
2A-4 X
3=OCH
3
6-N(CH
3)
2SO
2N(CH
3)
2A-2 X
1=CH
3Y
1=CH
2
6-N(CH
3)
2SO
2N(CH
3)
2A-3 X
1=CH
3
6-N(CH
3)
2SO
2N(CH
3)
2A-3 X
1=OCH
3
6-N(CH
3)
2SO
2N(CH
3)
2A-4 X
3=OCH
3
6-NHCH
3CO
2CH
3A-2 X
1=CH
3Y
1=CH
2
6-NHCH
3CO
2CH
3A-3 X
1=CH
3
6-NHCH
3CO
2CH
3A-3 X
1=OCH
3
6-NHCH
3CO
2CH
3A-4 X
3=OCH
3
6-OCH
3SO
2NHOCH
3A-2 X
1=CH
3Y
1=CH
2
6-OCH
3SO
2NHOCH
3A-3 X
1=CH
3
6-OCH
3SO
2NHOCH
3A-3 X
1=OCH
3
6-OCH
3SO
2NHOCH
3A-4 X
3=OCH
3
6-SCH
3SO
2NHOCH
3A-2 X
1=CH
3Y
1=CH
2
6-SCH
3SO
2NHOCH
3A-3 X
1=CH
3
6-SCH
3SO
2NHOCH
3A-3 X
1=OCH
3
6-SCH
3SO
2NHOCH
3A-4 X
3=OCH
3
Table VII (continuing)
R
1R
2A X Y m.p.(℃)
6-N(CH
3)
2SO
2NHOCH
3A-2 X
1=CH
3Y
1=CH
2
6-N(CH
3)
2SO
2NHOCH
3A-3 X
1=CH
3
6-N(CH
3)
2SO
2NHOCH
3A-3 X
1=OCH
3
6-N(CH
3)
2SO
2NHOCH
3A-4 X
3=OCH
3
6-NHCH
3SO
2NHOCH
3A-2 X
1=CH
3Y
1=CH
2
6-NHCH
3SO
2NHOCH
3A-3 X
1=CH
3
6-NHCH
3SO
2NHOCH
3A-3 X
1=OCH
3
6-NHCH
3SO
2NHOCH
3A-4 X
3=OCH
3
6-OCH
3CO
2CH
2CH
3A-2 X
1=CH
3Y
1=CH
2
6-OCH
3CO
2CH
2CH
3A-3 X
1=CH
3
6-OCH
3CO
2CH
2CH
3A-3 X
1=OCH
3
6-OCH
3CO
2CH
2CH
3A-4 X
3=OCH
3
6-OCH
3CO
2CH
2CH
3A-2 X
1=CH
3Y
1=CH
2
6-OCH
3CO
2CH
2CH
3A-3 X
1=CH
3
6-OCH
3CO
2CH
2CH
3A-3 X
1=OCH
3
6-OCH
3CO
2CH
2CH
3A-4 X
3=OCH
3
6-OCH
3CO
2CH
2CH
3A-2 X
1=CH
3Y
1=CH
2
6-OCH
3CO
2CH
2CH
3A-3 X
1=CH
3
6-OCH
3CO
2CH
2CH
3A-3 X
1=OCH
3
6-OCH
3CO
2CH
2CH
3A-4 X
3=OCH
3
6-OCH
3CO
2CH
2CH
3A-2 X
1=CH
3Y
1=CH
2
6-OCH
3CO
2CH
2CH
3A-3 X
1=CH
3
6-OCH
3CO
2CH
2CH
3A-3 X
1=OCH
3
6-OCH
3CO
2CH
2CH
3A-4 X
3=OCH
3
The table VIII
General formula 8
R
1R
3A X Y m.p.(℃)
H SOCH
3A-2 X
1=CH
3Y
1=CH
2
H SOCH
3A-3 X
1=CH
3
H SOCH
3A-3 X
1=OCH
3
H SOCH
3A-4 X
3=OCH
3
H SOCH
2CH
3A-2 X
1=CH
3Y
1=CH
2
H SOCH
2CH
3A-3 X
1=CH
3
H SOCH
2CH
3A-3 X
1=OCH
3
H SOCH
2CH
3A-4 X
3=OCH
3
H SOCH
2CH
2CH
3A-2 X
1=CH
3Y
1=CH
2
H SOCH
2CH
2CH
3A-3 X
1=CH
3
H SOCH
2CH
2CH
3A-3 X
1=OCH
3
H SOCH
2CH
2CH
3A-4 X
3=OCH
3
H S-cyclopropyl A-2 X
1=CH
3Y
1=CH
2
H S-cyclopropyl A-3 X
1=CH
3
H S-cyclopropyl A-3 X
1=OCH
3
H S-cyclopropyl A-4 X
3=OCH
3
H SO
2-cyclopropyl A-2 X
1=CH
3Y
1=CH
2
H SO
2-cyclopropyl A-3 X
1=CH
3
H SO
2-cyclopropyl A-3 X
1=OCH
3
H SO
2-cyclopropyl A-4 X
3=OCH
3
Table VIII (continuing)
R
1R
3A X Y m.p.(℃)
H OSO
2CH
3A-2 X
1=CH
3Y
1=CH
2
H OSO
2CH
3A-3 X
1=CH
3
H OSO
2CH
3A-3 X
1=OCH
3
H OSO
2CH
3A-4 X
3=OCH
3
H OSO
2CH
2CH
3A-2 X
1=CH
3Y
1=CH
2
H OSO
2CH
2CH
3A-3 X
1=CH
3
H OSO
2CH
2CH
3A-3 X
1=OCH
3
H OSO
2CH
2CH
3A-4 X
3=OCH
3
H OSO
2CF
3A-2 X
1=CH
3Y
1=CH
2
H OSO
2CF
3A-3 X
1=CH
3
H OSO
2CF
3A-3 X
1=OCH
3
H OSO
2CF
3A-4 X
3=OCH
3
H OSO
2CCl
3A-2 X
1=CH
3Y
1=CH
2
H OSO
2CCl
3A-3 X
1=CH
3
H OSO
2CCl
3A-3 X
1=OCH
3
H OSO
2CCl
3A-4 X
3=OCH
3
H CH
2F A-2 X
1=CH
3Y
1=CH
2
H CH
2F A-3 X
1=CH
3
H CH
2F A-3 X
1=OCH
3
H CH
2F A-4 X
3=OCH
3
Table VIII (continuing)
R
1R
3A X Y m.p.(℃)
H SO
2NHCH
3A-2 X
1=CH
3Y
1=CH
2
H SO
2NHCH
3A-3 X
1=CH
3
H SO
2NHCH
3A-3 X
1=OCH
3
H SO
2NHCH
3A-4 X
3=OCH
3
H CO
2CH
2CH
2OH A-2 X
1=CH
3Y
1=CH
2
H CO
2CH
2CH
2OH A-3 X
1=CH
3
H CO
2CH
2CH
2OH A-3 X
1=OCH
3
H CO
2CH
2CH
2OH A-4 X
3=OCH
3
H CO
2CH
2CH
2CN A-2 X
1=CH
3Y
1=CH
2
H CO
2CH
2CH
2CN A-3 X
1=CH
3
H CO
2CH
2CH
2CN A-3 X
1=OCH
3
H CO
2CH
2CH
2CN A-4 X
3=OCH
3
H CO
2CH
2CF
3A-2 X
1=CH
3Y
1=CH
2
H CO
2CH
2CF
3A-3 X
1=CH
3
H CO
2CH
2CF
3A-3 X
1=OCH
3
H CO
2CH
2CF
3A-4 X
3=OCH
3
The table IX
General formula 9
R
fR
4A X Y m.p.(℃)
H SOCH
3A-2 X
1=CH
3Y
1=CH
2
H SOCH
3A-3 X
1=CH
3
H SOCH
3A-3 X
1=OCH
3
H SOCH
3A-4 X
3=OCH
3
H SOCH
2CH
3A-2 X
1=CH
3Y
1=CH
2
H SOCH
2CH
3A-3 X
1=CH
3
H SOCH
2CH
3A-3 X
1=OCH
3
H SOCH
2CH
3A-4 X
3=OCH
3
H SOCH
2CH
2CH
3A-2 X
1=CH
3Y
1=CH
2
H SOCH
2CH
2CH
3A-3 X
1=CH
3
H SOCH
2CH
2CH
3A-3 X
1=OCH
3
H SOCH
2CH
2CH
3A-4 X
3=OCH
3
H S-cyclopropyl A-2 X
1=CH
3Y
1=CH
2
H S-cyclopropyl A-3 X
1=CH
3
H S-cyclopropyl A-3 X
1=OCH
3
H S-cyclopropyl A-4 X
3=OCH
3
H SO-cyclopropyl A-2 X
1=CH
3Y
1=CH
2
H SO-cyclopropyl A-3 X
1=CH
3
H SO-cyclopropyl A-3 X
1=OCH
3
H SO-cyclopropyl A-4 X
3=OCH
3
H SO
2-cyclopropyl A-2 X
1=CH
3Y
1=CH
2
H SO
2-cyclopropyl A-3 X
1=CH
3
H SO
2-cyclopropyl A-3 X
1=OCH
3
H SO
2-cyclopropyl A-4 X
3=OCH
3
Table IX (continuing)
R
fR
4A X Y m.p.(℃)
H OSO
2CH
3A-2 X
1=CH
3Y
1=CH
2
H OSO
2CH
3A-3 X
1=CH
3
H OSO
2CH
3A-3 X
1=OCH
3
H OSO
2CH
3A-4 X
3=OCH
3
H OSO
2CH
2CH
3A-2 X
1=CH
3Y
1=CH
2
H OSO
2CH
2CH
3A-3 X
1=CH
3
H OSO
2CH
2CH
3A-3 X
1=OCH
3
H OSO
2CH
2CH
3A-4 X
3=OCH
3
H OSO
2CF
3A-2 X
1=CH
3Y
1=CH
2
H OSO
2CF
3A-3 X
1=CH
3
H OSO
2CF
3A-3 X
1=OCH
3
H OSO
2CF
3A-4 X
3=OCH
3
H CH
2F A-2 X
1=CH
3Y
1=CH
2
H CH
2F A-3 X
1=CH
3
H CH
2F A-3 X
1=OCH
3
H CH
2F A-4 X
3=OCH
3
H CN A-2 X
1=CH
3Y
1=CH
2
H CN A-3 X
1=CH
3
H CN A-3 X
1=OCH
3
H CN A-4 X
3=OCH
3
Table IX (continuing)
R
fR
4A X Y m.p.(℃)
H SO
2N(OCH
3)CH
3A-2 X
1=CH
3Y
1=CH
2
H SO
2N(OCH
3)CH
3A-3 X
1=CH
3
H SO
2N(OCH
3)CH
3A-3 X
1=OCH
3
H SO
2N(OCH
3)CH
3A-4 X
3=OCH
3
H SO
2NHCH
3A-2 X
1=CH
3Y
1=CH
2
H SO
2NHCH
3A-3 X
1=CH
3
H SO
2NHCH
3A-3 X
1=OCH
3
H SO
2NHCH
3A-4 X
3=OCH
3
H CO
2CH
2CH
2OH A-2 X
1=CH
3Y
1=CH
2
H CO
2CH
2CH
2OH A-3 X
1=CH
3
H CO
2CH
2CH
2OH A-3 X
1=OCH
3
H CO
2CH
2CH
2OH A-4 X
3=OCH
3
H CO
2CH
2CH
2CN A-2 X
1=CH
3Y
1=CH
2
H CO
2CH
2CH
2CN A-3 X
1=CH
3
H CO
2CH
2CH
2CN A-3 X
1=OCH
3
H CO
2CH
2CH
2CN A-4 X
3=OCH
3
H CO
2CH
2CF
3A-2 X
1=CH
3Y
1=CH
2
H CO
2CH
2CF
3A-3 X
1=CH
3
H CO
2CH
2CF
3A-3 X
1=OCH
3
H CO
2CH
2CF
3A-4 X
3=OCH
3
The table X
General formula 10
R
fR
5A X Y m.p.(℃)
H SOCH
3A-2 X
1=CH
3Y
1=CH
2
H SOCH
3A-3 X
1=CH
3
H SOCH
3A-3 X
1=OCH
3
H SOCH
3A-4 X
3=OCH
3
H SOCH
2CH
3A-2 X
1=CH
3Y
1=CH
2
H SOCH
2CH
3A-3 X
1=CH
3
H SOCH
2CH
3A-3 X
1=OCH
3
H SOCH
2CH
3A-4 X
3=OCH
3
H SOCH
2CH
2CH
3A-2 X
1=CH
3Y
1=CH
2
H SOCH
2CH
2CH
3A-3 X
1=CH
3
H SOCH
2CH
2CH
3A-3 X
1=OCH
3
H SOCH
2CH
2CH
3A-4 X
3=OCH
3
H SO
2CH
3A-2 X
1=CH
3Y
1=CH
2
H SO
2CH
3A-3 X
1=CH
3
H SO
2CH
3A-3 X
1=OCH
3
H SO
2CH
3A-4 X
3=OCH
3
H SO
2CH
2CH
3A-2 X
1=CH
3Y
1=CH
2
H SO
2CH
2CH
3A-3 X
1=CH
3
H SO
2CH
2CH
3A-3 X
1=OCH
3
H SO
2CH
2CH
3A-4 X
3=OCH
3
H SO
2CH
2CH
2CH
3A-2 X
1=CH
3Y
1=CH
2
H SO
2CH
2CH
2CH
3A-3 X
1=CH
3
H SO
2CH
2CH
2CH
3A-3 X
1=OCH
3
H SO
2CH
2CH
2CH
3A-4 X
3=OCH
3
H S-cyclopropyl A-2 X
1=CH
3Y
1=CH
2
H S-cyclopropyl A-3 X
1=CH
3
H S-cyclopropyl A-3 X
1=OCH
3
H S-cyclopropyl A-4 X
3=OCH
3
H SO-cyclopropyl A-2 X
1=CH
3Y
1=CH
2
H SO-cyclopropyl A-3 X
1=CH
3
H SO-cyclopropyl A-3 X
1=OCH
3
Table X (continuing)
R
fR
5A X Y m.p.(℃)
H SO-cyclopropyl A-4 X
3=OCH
3
H SO
2-cyclopropyl A-2 X
1=CH
3Y
1=CH
2
H SO
2-cyclopropyl A-3 X
1=CH
3
H SO
2-cyclopropyl A-3 X
1=OCH
3
H SO
2-cyclopropyl A-4 X
3=OCH
3
H OSO
2CH
3A-2 X
1=CH
3Y
1=CH
2
H OSO
2CH
3A-3 X
1=CH
3
H OSO
2CH
3A-3 X
1=OCH
3
H OSO
2CH
3A-4 X
3=OCH
3
H CH
2F A-2 X
1=CH
3Y
1=CH
2
H CH
2F A-3 X
1=CH
3
H CH
2F A-3 X
1=OCH
3
H CH
2F A-4 X
3=OCH
3
H CN A-2 X
1=CH
3Y
1=CH
2
H CN A-3 X
1=CH
3
H CN A-3 X
1=OCH
3
H CN A-4 X
3=OCH
3
Table X (continuing)
R
fR
5A X Y m.p.(℃)
H SO
2N(OCH
3)CH
3A-2 X
1=CH
3Y
1=CH
2
H SO
2N(OCH
3)CH
3A-3 X
1=CH
3
H SO
2N(OCH
3)CH
3A-3 X
1=OCH
3
H SO
2N(OCH
3)CH
3A-4 X
3=OCH
3
H SO
2NHCH
3A-2 X
1=CH
3Y
1=CH
2
H SO
2NHCH
3A-3 X
1=CH
3
H SO
2NHCH
3A-3 X
1=OCH
3
H SO
2NHCH
3A-4 X
3=OCH
3
H SO
2NHCH
2CH
3A-2 X
1=CH
3Y
1=CH
2
H SO
2NHCH
2CH
3A-3 X
1=CH
3
H SO
2NHCH
2CH
3A-3 X
1=OCH
3
H SO
2NHCH
2CH
3A-4 X
3=OCH
3
H CO
2CH
2CH
2OH A-2 X
1=CH
3Y
1=CH
2
H CO
2CH
2CH
2OH A-3 X
1=CH
3
H CO
2CH
2CH
2OH A-3 X
1=OCH
3
H CO
2CH
2CH
2OH A-4 X
3=OCH
3
H CO
2CH
2CH
2CN A-2 X
1=CH
3Y
1=CH
2
H CO
2CH
2CH
2CN A-3 X
1=CH
3
H CO
2CH
2CH
2CN A-3 X
1=OCH
3
H CO
2CH
2CH
2CN A-4 X
3=OCH
3
H CO
2CH
2CF
3A-2 X
1=CH
3Y
1=CH
2
H CO
2CH
2CF
3A-3 X
1=CH
3
H CO
2CH
2CF
3A-3 X
1=OCH
3
H CO
2CH
2CF
3A-4 X
3=OCH
3
Preparation
The practical preparation of the compound of available ordinary method preparation formula I.They comprise pulvis, particle, pill, solution, suspension, emulsion, wettable powder, emulsifiable concentrate or the like.Many can directly the use wherein arranged.Sprayable preparation can be spread in the suitable media, and the sprayed volume of using is raised to several hectolitres as per hectare is several.The high strength composition is mainly as the intermediate of further preparing.In general, contain about 0.1% to 99%(weight in the said preparation) active ingredient and at least a (a) about tensio-active agent of 0.1 to 20% and (b) about 1% to 99.9% solid or liquid inert diluent.More particularly, they will contain these compositions with following general proportions:
Weight percent *
Active ingredient thinner tensio-active agent
Wettable powder 20-90 0-74 1-10
Oily suspension 3-50 40-95 0-15
Emulsion, solution
But (comprise emulsification
Enriched material)
Aqeous suspension 10-50 40-84 1-20
Pulvis 1-25 70-99 0-5
Particle and pill 0.1-95 5-99.9 0-15
High strength composition 90-99 0-10 0-2
* active ingredient adds that at least a tensio-active agent or thinner equal 100%(weight).
Certainly, the purposes as required and the physical properties of compound can have lower or higher levels of active ingredient.Tensio-active agent is favourable to the higher proportion of active ingredient sometimes, can be by mixing in the preparation or mixing in jar and finish.
The typical solid thinner is described in people's such as Watkins " Handbook of Insecticide Dust Diluents and Carriers " the 2nd edition, Dorland Books, Caldwell, New Jersey, but also can use other solids, mineral substance or people's chemical product can.For wettable powder, the thinner that adsorptivity is stronger is better, and is better for the pulvis thinner that then density is bigger.Typical liquid diluent and solvent are described in Marsden, " Solvents Guide " the 2nd edition, Interscience, New York, 1950.Solubleness is best below 0.1% for suspension-concentrates, and the solution concentration thing is stable for being separated under 0 ° preferably." McCutcheon ' s Detergents and Emulsifiers Annual ", MC Publishing Corp., Ridgewood, New Jersey, and Sisely and Wood, " Encyclopedia of Surface Active Agents ", Chemical Publishing Co., Inc., New York, 1964, listed the purposes of various tensio-active agents and recommendation.All preparations can contain a small amount of additive to reduce foam, caking, burn into microorganism growth or the like.
Preparing such method for compositions knows.Prepare solution by each component of simple mixing.The pulverulent solids composition normally grinds in hammer mill or fluid driving mill (fluid energymill) by grinding preparation.Suspension can prepare (referring to for example, Littler, United States Patent (USP) 3,060,084) by wet-milling.Particle and pill can prepare by active substance being sprayed on the preliminary shaping particulate vector or by the reunion technology.Referring to J.E.Browning, " Agglomeration ", Chemical Engineering, on December 4th, 1967, pp.147ff and " Perry ' s Chemical Engineering ' s Handbook " the 5th edition, Mc Graw-Hill, New York, 1963, pp.8-57ff.
About the further data of compounding process, referring to for example,
H.M.Loux, United States Patent (USP) 3,235,361(1966 February 15), the 6th hurdle the 16th walks to the 7th hurdle the 19th row and example 10 to 41,
R.W.Luckenbaugh, United States Patent (USP) 3,309,192(1967 March 14), the 5th hurdle 43 walks to the 7th hurdle 62 row and example 8,12,15,39,41,52,53,58,132,138-140,162-164,166,167 and 169-182;
H.Gysin and E.Knusli, United States Patent (USP) 2,891,855(1959 June 23), the 3rd hurdle 66 walks to the 5th hurdle 17 row and example 1-4;
G.C.Klingman,《Weed????Control????as????a????Science》,John????Wiley????and????Sons,Inc.,New????York,1961,pp.81-96;
J.D.Fryer and S.A.Evans, " Weed Control Handbook " the 5th edition, Blackwell Scientific Publications, Oxford, 1968, pp.101-103.
In following example, unless otherwise noted, all shares all are meant weight.
Example 24
The high strength enriched material
N2-[(4,6-dimethoxypyridin-2-yl) aminocarboxyl]-N3-methyl 2,3-pyridine two sulfanilamide (SN) 99%
Trimethylammonium nonyl polyglycol ether 1%
In blending machine, tensio-active agent is sprayed on the active ingredient, before the packing, this mixture is sieved by No. 40 sieves of USS (0.42mm aperture).For this enriched material of practical application can further be prepared.
Example 25
Wettable powder
2-[[(4,6-dimethoxypyridin-2-yl) aminocarboxyl]-amino-sulfonyl]-3-pyridine carboxylic acid methyl ester 65%
Dodecyl phenol polyglycol ether 2%
Sodium lignosulfonate 4%
Sodium silicoaluminate 6%
Montmorillonite (burnt) 23%
With each component thorough mixing.In blending machine, add liquid surfactant by spraying on solid ingredient.In hammer mill, grind make generation particle basically all less than after 100 microns, mix this material once more, then by No. 50 sieves of USS (0.3mm aperture) screening and packing.
Example 26
Aqeous suspension
N2-[(4,6-dimethoxypyridin-2-yl) aminocarboxyl]-N3-methyl-2,3 pyridine two sulfanilamide (SN) 50.0%
Polyacrylate thickeners 0.3%
Dodecyl phenol polyglycol ether 0.5%
Sodium phosphate dibasic 1%
SODIUM PHOSPHATE, MONOBASIC 0.5%
Polyvinyl alcohol 1.0%
Water 56.7%
Mixed being incorporated in the husky mill of each component ground together, produce big or small basically all at the particle below 5 microns.
Example 27
Oily suspension
N[(4,6-dimethoxypyridin-2-yl) aminocarboxyl]-3-(1-sulfonyl propyl base)-2-Sulphapyridine methyl ester 35%
The mixture 6% of poly-alcohol carboxylate and oil soluble sulfonated petro-leum
Dimethylbenzene 59%
Each component is merged and grinding together in the sand mill, produce basically all at the particle below 3 microns.This product can directly use, also usable oils diffusion or emulsification in water.
Example 28
Oily suspension
N[(4,6-dimethoxypyridin-2-yl) aminocarboxyl]-the 3-(1-mesyloxy)-2-Sulphapyridine methyl ester 25%
Polyoxyethylene sorbitol six oleic acid esters 5%
Senior aliphatic hydrocarbon oil 70%
Each component is ground in sand mill together, until solid particulate reduce to about below 5 microns till.The thickness suspension of gained can directly use, but preferably with oil diffusion or in water, use after the emulsification.
Example 29
Aqeous suspension
N[(4,6-dimethoxypyridin-2-yl) aminocarboxyl]-the 3-(1-ethylsulfonyl)-2-Sulphapyridine methyl ester 25%
Hydration attapulgite (hydrated attapulgite) 3%
Rough calcium lignin sulphonate 10%
SODIUM PHOSPHATE, MONOBASIC 0.5%
Water 61.5%
Each component is ground in ball milling or barreling together, till the diameter of solid particulate is reduced to below 10 microns.
Example 29
Wettable powder
N2-[(4,6-dimethoxypyridin-2-yl) aminocarboxyl]-N3-methyl-2,3-pyridine two sulfanilamide (SN) 40.0%
Dioctyl sulfo-sodium succinate 1.5%
Sodium lignosulfonate 3%
Low viscosity methylcellulose gum 1.5%
Attapulgite 54%
With each component thorough mixing, produce mean size at the particle below 15 microns by the gas mill, remix, and by No. 50 sieves of USS (0.3mm aperture) screening, pack then.
All available this identical mode of all compounds of the present invention is prepared.
Example 30
Particle
Wettable powder 15% in the example 29
Gypsum 69%
Vitriolate of tartar 16%
With the fusion and spray moisture in impeller of each component to form particle.When most of raw materials reach No. 18 to 40, desired 1.0 to 0.42cm(USS sieve) scope the time, particle is taken out dry and screening.Excessive particle is pulverized to obtain new particle within the required range.These particles contain the active ingredient of %.
Example 31
Wettable powder
N[(4,6-dimethoxypyridin-2-yl) aminocarboxyl]-the 3-(ethylsulfonyl)-2-Sulphapyridine methyl ester 50%
Sodium alkyl naphthalene sulfonate 2%
Low viscosity methylcellulose gum 2%
Diatomite 46%
Each component is mixed, roughly grind laggard promoting the circulation of qi mill to produce diameter basically all at the active particle below 10 microns with hammer mill.Pack behind this product remix.
Example 32
The extruding pill
N[(4,6-dimethoxypyridin-2-yl) aminocarboxyl]-the 3-(ethylsulfonyl)-2-Sulphapyridine 25%
Anhydrous sodium sulphate 10%
Rough calcium lignin sulphonate 5%
Sodium alkyl naphthalene sulfonate 1%
Calcium/magnesium wilkinite 59%
Each component is mixed, and sledge mill uses about 12% water moistening then.This mixture is extruded with the cylinder of the about 3mm of diameter, cuts off then to form the long pill of about 3mm.These pills can directly use after drying, perhaps can make the exsiccant pill pulverize the back by No. 20 sieves of USS (0.84mm aperture).The particle that is retained on No. 40 sieves of USS (0.42mm aperture) can package spare, and fine powder can recirculation.
Example 33
Wettable powder
N[(4,6-dimethoxypyridin-2-yl) aminocarboxyl]-the 3-(1-ethylsulfonyl)-2-Sulphapyridine 80%
Sodium alkyl naphthalene sulfonate 2%
Sodium lignosulfonate 2%
Synthetic amorphous silica 3%
Kaolin 13%
Each component is mixed the back in hammer mill, grind, so that to obtain mean particle size be diameter less than 25 microns particle.This material is mixed once more, and, pack then by No. 50 sieves of USS (0.3mm aperture) screening.
Example 34
The high strength enriched material
N[(4,6-dimethoxypyridin-2-yl) aminocarboxyl]-the 3-(1-ethylsulfonyl)-2-Sulphapyridine 98.5%
Siliceous reinforcing agent 0.5%
The amorphous fine silica powder 1.0% of synthetic
Each component is mixed, and in hammer mill, grind to produce basically and can both sieve the high strength enriched material in (0.3mm aperture) No. 50 by USS.This material can several different methods be prepared then.
Example 35
Wettable powder
2-[[(4,6-dimethoxypyridin-2-yl) aminocarboxyl]-amino-sulfonyl]-3-pyridine carboxylic acid methyl ester 80%
Sodium alkyl naphthalene sulfonate 2%
Sodium lignosulfonate 2%
Synthetic amorphous silicon 3%
Kaolin 13%
Each component is mixed, then in grinding in ball grinder so that to obtain mean particle size be diameter less than 25 microns particle.This material is mixed once more, and, pack then by No. 50 sieves of USS (0.3mm aperture) screening.
Example 36
The high strength enriched material
N2[(4,6-dimethoxypyridin-2-yl) aminocarboxyl]-N3-methyl-2,3-pyridine two sulfanilamide (SN) 98.5%
Siliceous reinforcing agent 0.5%
The amorphous fine silica powder 1.0% of synthetic
Mixed being incorporated in the hammer mill of each component ground, basically can both be to produce by the high strength enriched material of No. 50 sieves of USS (0.3mm aperture).This material can several different methods be prepared then.
Practicality
Test result shows, The compounds of this invention is highly actively to sprout preceding or sprout back weedkiller or plant-growth regulator.Wherein have many have sprouting of wide spectrum preceding and/or sprout after the purposes of inhibition weeds, can be used for to suppress fully the place of all plant-growths, for example near the fuel storage jar, the industry storage area, the parking lot, near the open-air theater (drive-in theaters), billboard, highway and railway building etc.Some compound can be used for selectivity and suppress weeds in crop-planting.Solanaceous crops is tomato, potato and capsicum for example, other crops for example wheat, barley, corn, cotton or soybean and slack season thereof ground.Before some compound of the present invention especially can suppress to sprout in corn (maize) and the weeds after sprouting, and to not obviously injury of crop.Some compound of the present invention also can suppress weeds and not obvious injury crop in potato (Solanum tuberosum) and tomato (Lycopersicon esculentum).They are particularly useful for suppressing the weeds of some refractories, for example Herba Setariae Viridis (Setaria spp.), foreign wild broomcorn millet (Panicum dichotomiflorum), barnyard grass (Echinochloa crusgalli), stone thatch Chinese sorghum (Sorghum halepense) and two look Chinese sorghums (Sorghum bicolor) like this.They can sprout preceding or the back use of sprouting, and the young grass that is used for just having sprouted is the most effective.They also are effectively for some broadleaf weeds, these weeds such as lamb's-quarters (Chenopodium album), amaranth (Amaranthus spp.) and piemarker (Abutilon theophrasti).
In addition, compound of the present invention can be used for coordinate plant growth.
The ratio of using of The compounds of this invention is determined by some factors, these factors comprise that they are to use as plant-growth regulator or as weedkiller, the related species of doing, the type of the weeds that suppress, weather condition and local climate, choice of formulation, the blade amount of method of application and existence etc.Under general condition, the level of using of The compounds of this invention should be approximately 0.001-20kg/ha, the low ratio of being advised is to be used for light earth (lighter soil) and/or the lower soil of organic content, is used for plant growth regulating or is used for the only of short duration persistent situation of needs.
Compound of the present invention can be used in combination with any other commercial weedkiller, and their example is the weedkiller of triazine, diazole, imidazolone, uridylic, urea, acid amides, diphenyl ether, Terpane, carbamate and bipyridine cation type (bipyridylium types).They especially can be used in combination with following weedkiller.
The popular name chemical name
Alachlor 2-chloro-2 ', 6 '-diethyl-N-(methoxymethyl)-monoacetylaniline
Atrazine 2-chloro-4-(ethylamino)-6-(sec.-propyl ammonia
Base)-the S-triazine
Butylate diisobutyl thiocarbamate S-ethyl ester
Bladex 2-[[4-chloro-6-(ethylamino)-the S-triazine
-2-yl] amino]-2-methyl propionitrile
Dicamba 98 3,6-two chloro-o-methoxybenzoic acids
Eptam dipropyl thiocarbamate S-ethyl ester
Methoxydiuron 3-(3,4 dichlorophenyls)-1-methoxyl group-1-methyl
Urea
Metolachlor 2-chloro-N-(2-ethyl-6-aminomethyl phenyl)-N
-(2-methoxyl group-1-methylethyl) ethanamide
The sencorex 4-amino-6-tertiary butyl-3-(methylthio group)-as-
Triazine-5(4H)-ketone
Tridiphane 2-(3, the 5-dichlorophenyl)-2-(2,2, the 2-trichlorine
Ethyl) oxyethane
2,4-D (2,4 dichloro benzene oxygen base) acetate
Bromoxynil 3,5-two bromo-4-hydroxyphenyl cyanides
Paraquat 1,1 '-dimethyl-4,4 '-bipyridine cation
Glyphosate N-((phosphonomethyl)) glycine
Chlorthal tetrachloro-p-phenylene two dimethyl phthalates
The dalapon 2,2 dichloropropionic acid
The eastern phenol 2-(1-methyl-propyl in ground)-4, the 6-dinitrophenol(DNP)
Enide N, N-dimethyl-2,2-phenylbenzene ethanamide
Pendimethalin N-(1-ethyl propyl)-3,4-dimethyl-2,6-
Dinitraniline
Oryzalin 3,5-dinitrobenzene-N, the N-dipropyl is to amino
Benzsulfamide
The clever α in fluorine east, α, α-three fluoro-2,6-dinitrobenzene-N,
N-dipropyl-right-Tolylamine
Amiben 3-amino-2, the 5-dichlorobenzoic acid
R-7465 2-(alpha-naphthoxy base)-and N, N-diethyl third
Acid amides
Pebulate S-propyl group butyl ethyl thiocarbamate
Between Y 3-chlorobenzene carboxylamine isopropyl esters
Bensulide N-(2-mercaptoethyl) S-(O of benzsulfamide,
The O-diisopropyl disulfide is for phosphoric acid) ester
The trade name chemical name
Harmony
TM3-[[(4-methoxyl group-6-methyl isophthalic acid, 3,5-
Triazine-2-yl) aminocarboxyl] aminosulfonyl
Base]-2-thio phenyl carboxylic acid methyl ester
-aminomethyl phenyl)-methoxyl group]-the 7-oxabicyclo
-[2.2.1] heptane
-2-oxyethyl group-N-[[4-(2,2, the 2-trifluoro
Oxyethyl group)-6-methoxyl group-1,3,5-triazines-2-
Base] aminocarboxyl] benzsulfamide
Compound
Compound R
2R R
1X Y Z
1 SO
2CH
2CH
2CH
3H H OCH
3OCH
3CH
2 SO
2CH
2CH
2CH
3H H CH
3OCH
3CH
3 SO
2CH
2CH
2CH
3H H Cl OCH
3CH
4 SO
2CH
2CH
2CH
3H H CH
3CH
3CH
5 SO
2CH
2CH
2CH
3H H OCH
3OCH
3N
6 SO
2CH
2CH
2CH
3H H CH
3OCH
3N
7 SO
2CH
2CH
2CH
3H H OCH
2CH
3NHCH
3N
8 S(O)CH
2CH
2CH
3H H OCH
3OCH
3CH
9 S(O)CH
2CH
2CH
3H H CH
3OCH
3CH
10 S(O)CH
2CH
2CH
3H H Cl OCH
3CH
11 S(O)CH
2CH
2CH
3H H CH
3CH
3CH
12 S(O)CH
2CH
2CH
3H H OCH
3OCH
3N
13 S(O)CH
2CH
2CH
3H H CH
3OCH
3N
14 S(O)CH
2CH
2CH
3H H OCH
2CH
3NHCH
3N
15 S(O)CH
2CH
3H H OCH
3OCH
3CH
16 S(O)CH
2CH
3H H OCH
3CH
3CH
17 S(O)CH
2CH
2CH
3H H Cl OCH
3CH
18 S(O)CH
2CH
3H H CH
3CH
3CH
19 S(O)CH
2CH
3H H OCH OCH
3N
20 S(O)CH
2CH
3H H OCH
3CH
3N
21 SO
2CH
2CH
3H H OCH
3OCH
3CH
22 SO
2CH
2CH
3H H OCH
3CH
3CH
23 SO
2CH
2CH
3H H Cl OCH
3CH
Compound (continuing)
Compound R
2R R
1X Y Z
24 SO
2CH
2CH
3H H CH
3CH
3CH
25 SO
2CH
2CH
3H H OCH
3OCH
3N
26 SO
2CH
2CH
3H H OCH
3CH
3N
27 SO
2CH
2CH
3CH
3H OCH
3CH
3N
28 S(O)CH
3H H OCH
3OCH
3CH
29 S(O)CH
3H H OCH
3CH
3CH
30 S(O)CH
3H H Cl OCH
3CH
31 S(O)CH
3H H CH
3CH
3CH
32 S(O)CH
3H H OCH
3CH
3N
33 S(O)CH
3CH
3H OCH
3CH
3N
34 SO
2CH
3H H OCH
3OCH
3CH
35 SO
2CH
3H H OCH
3CH
3CH
36 SO
2CH
3H H Cl OCH
3CH
37 SO
2CH
3H H CH
3CH
3CH
38 SO
2CH
3H H OCH
3OCH
3N
39 SO
2CH
3H H OCH
3CH
3N
40 S(O)CH(CH
3)
2H H OCH
3OCH
3CH
41 S(O)CH(CH
3)
2H H OCH
3CH
3CH
42 S(O)CH(CH
3)
2H H Cl OCH
3CH
43 S(O)CH(CH
3)
2H H CH
3CH
3CH
44 S(O)CH(CH
3)
2H H OCH
3OCH
3N
45 S(O)CH(CH
3)
2H H OCH
3CH
3N
46 SO
2CH(CH
3)
2H H OCH
3OCH
3CH
47 SO
2CH(CH
3)
2H H OCH
3CH
3CH
48 SO
2CH(CH
3)
2CH
3H Cl OCH
3CH
49 SO
2CH(CH
3)
2H H CH
3CH
3CH
50 SO
2CH(CH
3)
2H H OCH
3OCH
3N
51 SO
2CH(CH
3)
2H H OCH
3CH
3N
52 SO
2CH(CH
3)
2CH
3H OCH
3CH
3N
53 SO
2(CH
2)
3CH
3H H OCH
3OCH
3CH
54 SO
2(CH
2)
3CH
3H H OCH
3CH
3CH
55 SO
2(CH
2)
3CH
3H H Cl OCH
3CH
Compound (continuing)
Compound R
2R R
1X Y Z
56 SO
2(CH
2)
3CH
3H H CH
3CH
3CH
57 SO
2(CH
2)
3CH
3H H OCH
3OCH
3N
58 SO
2(CH
2)
3CH
3H H OCH
3CH
3N
59 SO
2(CH
2)
3CH
3CH
3H OCH
3CH
3N
60 SO
2CH
2CH
3H CH
3OCH
3OCH
3CH
61 SO
2CH
2CH
3H CH
3OCH
3CH
3CH
62 SO
2CH
2CH
3H CH
3CH
3CH
3CH
63 SO
2CH
2CH
3H CH
3OCH
3CH
3N
64 SO
2CH
2CH
3H OCH
3OCH
3OCH
3CH
65 OSO
2CH
3H H OCH
3OCH
3CH
66 OSO
2CH
3H H OCH
3CH
3CH
67 OSO
2CH
3H H Cl OCH
3CH
68 OSO
2CH
3H H CH
3CH
3CH
69 OSO
2CH
3H H OCH
3CH
3N
70 OSO
2C
2H
5H H OCH
3OCH
3CH
71 OSO
2C
2H
5H H CH
3OCH
3CH
72 OSO
2C
2H
5H H Cl OCH
3CH
73 OSO
2C
2H
5H H CH
3CH
3CH
74 OSO
2C
2H
5H H OCH
3OCH
3N
75 OSO
2C
2H
5H H CH
3OCH
3N
76 SO
2C
2H
5H F OCH
3OCH
3CH
77 SO
2C
2H
5H F CH
3CH
3CH
78 SO
2C
2H
5H Cl OCH
3OCH
3CH
79 SO
2C
2H
5H Cl Cl OCH
3CH
80 SO
2C
2H
5H Cl CH
3CH
3CH
81 OSO
2CF
3H H OCH
3OCH
3CH
82 OSO
2CF
3H H Cl OCH
3CH
83 OSO
2CF
3H H CH
3CH
3CH
84 OSO
2CF
3H H OCH
3OCH
3N
85 OSO
2CF
3H H CH
3OCH
3N
86 CH
2Cl H H OCH
3OCH
3CH
87 CH
2Cl H H Cl OCH
3CH
Compound (continuing)
Compound R
2R R
1X Y Z
88 CH
2Cl H H CH
3OCH
3N
89 P(O)(OCH
2CH
3)
2H H OCH
3OCH
3CH
90 P(O)(OCH
2CH
3)
2H H CH
3OCH
3CH
91 P(O)(OCH
2CH
3)
2H H CH
3CH
3CH
Compound R
2R R
1X Y Z
92 SO
2NHCH
3H H OCH
3OCH
3CH
93 SO
2NHCH
3H H Cl OCH
3CH
94 SO
2NHCH
3H H CH
3CH
3CH
95 SO
2NHCH
3H H OCH
3CH
3N
96 SO
2N(OCH
3)CH
3H H OCH
3OCH
3CH
97 SO
2N(OCH
3)CH
3H H OCH
3CH
3CH
98 SO
2N(OCH
3)CH
3H H OCH
3CH
3N
99 SO
2N(OCH
2)CH
3CH
3H OCH
3CH
3N
100 SO
2NHCH
2CH
3H H OCH
3OCH
3CH
101 SO
2NHCH
2CH
3H H Cl OCH
3CH
102 SO
2NHCH
2CH
3H H CH
3CH
3CH
103 SO
2NHCH
2CH
3H H OCH
3OCH
3N
104 SO
2NHCH
2CH
3H H OCH
3CH
3N
105 SO
2NHCH
2CH
3H H OCH
3CH
3N
106 SO
2NHCH
2CH
2CH
3H H OCH
3OCH
3CH
107 SO
2NHCH
2CH
2CH
3H H CH
3OCH
3CH
108 SO
2NHCH
2CH
2CH
3H H Cl OCH
3CH
109 SO
2NHCH
2CH
2CH
3H H OCH
3OCH
3N
Compound (continuing)
Compound R
2R R
1X Y Z
112 CO
2CH
2Cyclopropyl H H OCH
3OCH
3CH
113 CO
2CH
2Cyclopropyl H H Cl OCH
3CH
114 CO
2CH
2Cyclopropyl H H CH
3CH
3CH
115 CO
2CH
2Cyclopropyl H H OCH
3OCH
3N
116 CO
2CH
3H OCH
3OCH
3OCH
3CH
117 CO
2CH
3H OCH
3CH
3OCH
3CH
118 CO
2CH
3H OCH
3Cl OCH
3CH
119 CO
2CH
3H OCH
3CH
3CH
3CH
120 CO
2CH
3H OCH
3OCH
3OCH
3N
121 CO
2CH
3H OCH
3CH
3OCH
3N
Test A
The seed of plantation following plants: big lady's-grass (Digitaria sanguinalis), barnyard grass (Echinochloa crus-galli), Herba Setariae viridis (Setaria faberi), wild avena sativa (Avena fatua), bromegrass (Bromus secalinus), piemarker (Abutilon theophrasti), cultivation sweet potato (Ipomoea coccinea, Scarlet O ' Hara kind), Siberian cocklebur (Xanthium pensylvanicum), G522 Chinese sorghum (Sorghum vulgare, Funk G522 kind), G4646 corn (Zea mays, Funk G4646 kind), WILLIAMS-DARLING Ton soybean (Glycine max, the Williams kind), USH11 beet (Beta vulgaris, Union Sugarbeet Co.USH11 kind), upland cotton (Gossypium hirsutum, Coker 315 kinds), do kind of a rice (Oryza sativa, California Rice Coop.M101 kind), Era wheat (Triticum aestivum, Era spring kind), Klages barley (Hordeum vulgare, Klages spring kind), with Rhizoma Cyperi (Cyperus rotundus) stem tuber, and with the pre-treatment of sprouting of the test medicine in the solvent that is dissolved in non-plant toxicity.Simultaneously, these crops and weeds are used by soil/blade and handle.When handling, the plant height scope is 2-18cm.Plant of handling and contrast kept 16 days at room temperature, then with all kinds with compare, and classification is carried out in the reaction of handling according to its visible.Table A has been summarized stage division, and classification not to be having injury from 0=, to the dead fully digital scale of 10=be basic.Appended descriptive symbol has following meaning:
C=chlorosis/necrosis
B=burns
The D=fallen leaves
E=goes out bud inhibition
The G=retarded growth
H=moulding effect
The U=abnormal pigmentation
X=armpit growth
The S=albinism;
6Y=bud or flower come off
" POSOL " in the Table A and " PRSOL " represent to sprout back respectively and the pre-treatment of sprouting.
Annotate: (1) upland cotton
(2) cultivation sweet potato
(3) Siberian cocklebur
(4) Rhizoma Cyperi
(5) big lady's-grass
(6) barnyard grass
(7) wild avena sativa
(8) Era wheat
(9) G4646 corn
(10) WILLIAMS-DARLING Ton soybean
(11) do kind of a rice
(12) G522 Chinese sorghum
(13) bromegrass
(14) USH11 beet
(15) piemarker
(16) Herba Setariae viridis
(17) Klages barley
(18) downy brome
CMPD: compound
Notice that for example compound 6,19,20,26,32,37-39,44,49,54-59,76-78 and 88 seldom or not show activity of herbicide to several compounds under the ratio of being tested.Perhaps, they use with higher ratio can show bigger activity of herbicide.
Test B
After sprouting
In 3 circular flowerpots (diameter 25cm, dark 12.5cm), fill the Sassafras silty loam.Plantation Rhizoma Cyperi stem tuber, big lady's-grass, senna (Cassia obtusifolia), thorn apple (Datura stramonium), piemarker, lamb's-quarters, dried kind of rice and Radix sidae acutae (Sida spinosa) are planted green green bristlegrass (Setaria viridis), Siberian cocklebur, cultivation sweet potato, upland cotton, stone thatch Chinese sorghum, barnyard grass, G4646 corn, WILLIAMS-DARLING Ton soybean and Herba Setariae viridis in the flowerpot in second flowerpot.Plantation Era wheat, Klages barley, volume stem knotweed (Polygonum convolvulus), bromegrass, USH11 beet, wild avena sativa, violet (Viola arvensis), amur foxtail (Alopecurus myosuroides) and Altex rape (Brassica napus, Altex kind) in the 3rd flowerpot.Allow about 14 days of these plant-growths, spray with the medicament that is dissolved in the non-plant toxicity solvent in the back of sprouting then.
Before sprouting
In 3 circular flowerpots (diameter 25cm, dark 12.5cm), fill the Sassafras silty loam.Plantation Rhizoma Cyperi stem tuber in the flowerpot, lady's-grass, senna, thorn apple, piemarker, lamb's-quarters,
Rice and Radix sidae acutae.Plant green green bristlegrass, Siberian cocklebur, sweet potato, cotton, stone thatch Chinese sorghum, barnyard grass, corn, soybean and Herba Setariae viridis in second basin.Plant wheat, barley, volume stem knotweed, bromegrass, beet, wild avena sativa, violet, amur foxtail and rape in the 3rd flowerpot.These three basins are used the reagent spray that is dissolved in the non-plant toxicity solvent before sprouting.
The plant of handling and kept 24 days to impinging upon in the greenhouse, then, with all other plants of level with compare, and plant reaction is estimated classification.
Level of reaction is based on 0 to 100 scale, and 0=does not have effect, and 100=suppresses fully.Strigula (-) reaction is meant and is provided with test.
Level of reaction is included among the table B.
Table B
CMPD????1
Ratio G/HA 0,001 0,004 0,016 0,062 0250
PRE
〔16〕????20????20????80????85????90
〔15〕????0????20????30????40????70
〔14〕????20????60????70????80????90
〔5〕????0????0????40????50????75
〔19〕????-????-????30????80????80
〔20〕????-????0????-????50????-
〔11〕????20????85????90????95????100
〔3〕????0????0????30????85????90
〔1〕????0????10????85????85????90
〔10〕????0????0????0????10????30
〔6〕????0????20????100????95????95
〔7〕????10????20????30????60????70
〔21〕????0????0????20????80????95
〔8〕????0????20????30????80????90
〔22〕????-????0????-????-????-
〔23〕????60????85????90????100????100
〔4〕????20????30????80????90????95
〔9〕????0????0????0????0????10
〔24〕????0????50????70????80????90
〔25〕????0????20????80????85????100
〔26〕????0????50????80????90????95
〔17〕????20????30????80????80????90
〔27〕????20????90????95????100????99
〔13〕????30????70????90????100????100
〔28〕????0????0????50????70????80
Table B(is continuous)
CMPD????1
Ratio G/HA 0.25 0,001 0,004 0016
POST
〔16〕????40????70????100????100
〔15〕????0????0????50????90
〔14〕????0????20????40????70
〔5〕????0????0????0????70
〔19〕????0????-????-????-
〔20〕????0????0????20????50
〔11〕????0????40????90????100
〔3〕????0????0????40????80
〔1〕????0????30????60????80
〔10〕????40????50????80????90
〔6〕????50????80????95????100
〔7〕????0????20????70????80
〔21〕????0????20????95????95
〔8〕????50????60????60????100
〔22〕????0????30????90????100
〔23〕????70????80????100????100
〔4〕????0????30????40????70
〔9〕????0????0????0????0
〔24〕????20????20????50????60
〔25〕????0????50????80????-
〔26〕????50????80????100????-
〔17〕????20????20????60????70
〔27〕????60????90????100????100
〔13〕????20????30????50????90
〔29〕????0????30????40????-
〔28〕????0????-????0????-
Table B(is continuous)
CMPD????21
Ratio G/HA 0,001 0,004 0,016 0062
PRE
〔16〕????30????70????90????100
〔15〕????30????50????70????90
〔14〕????30????60????90????100
〔5〕????30????50????70????90
〔19〕????30????50????70????90
〔20〕????60????70????80????90
〔11〕????60????100????100????100
〔3〕????0????30????50????70
〔1〕????0????30????50????80
〔10〕????0????0????30????90
〔6〕????30????60????90????100
〔7〕????0????0????30????80
〔21〕????0????30????60????90
〔8〕????0????30????60????90
〔23〕????50????70????80????90
〔4〕????0????30????80????100
〔5〕????0????0????0????0
〔24〕????70????80????90????90
〔25〕????60????70????80????90
〔26〕????70????90????100????100
〔17〕????30????50????80????90
〔27〕????30????70????100????100
〔13〕????30????70????100????100
〔29〕????30????50????70????90
〔28〕????50????60????70????90
Table B(is continuous)
CMPD????21
Ratio G/HA 0,001 0,004 0,016 0062
POST
〔16〕????30????50????80????90
〔15〕????30????60????80????100
〔14〕????-????50????70????90
〔5〕????0????0????30????50
〔19〕????0????20????40????60
〔20〕????0????0????30????60
〔11〕????30????50????70????90
〔3〕????30????40????50????60
〔1〕????0????30????50????60
〔10〕????0????30????60????90
〔6〕????50????70????80????90
〔7〕????-????0????30????60
〔21〕????30????30????70????80
〔8〕????-????50????80????100
〔22〕????0????30????60????90
〔23〕????30????60????90????100
〔4〕????0????30????60????90
〔9〕????-????0????0????0
〔24〕????-????50????70????90
〔25〕????-????50????70????100
〔26〕????-????90????100????100
〔17〕????-????50????60????70
〔27〕????30????50????70????80
〔18〕????-????50????70????90
〔28〕????0????0????30????50
〔30〕????-????50????70????90
Table B(is continuous)
CMPD????46
Ratio G/HA 0,004 0,016 0,062 0250
PRE
〔16〕????50????80????90????100
〔15〕????30????60????90????100
〔14〕????70????90????100????-
〔5〕????0????30????50????70
〔19〕????0????30????50????80
〔20〕????0????30????60????90
〔11〕????80????90????100????100
〔3〕????0????30????50????70
〔1〕????0????30????40????60
〔10〕????0????0????70????-
〔6〕????60????90????100????100
〔7〕????0????30????40????60
〔21〕????30????50????70????90
〔8〕????30????50????70????80
〔22〕????30????60????90????100
〔23〕????50????70????80????90
〔4〕????30????60????90????100
〔9〕????0????0????0????30
〔24〕????30????50????70????90
〔25〕????50????70????80????90
〔26〕????50????70????90????100
〔17〕????20????40????60????80
〔27〕????30????50????80????100
〔13〕????60????70????80????90
〔28〕????30????50????80????90
〔30〕????30????50????70????90
Table B(is continuous)
CMPD????46
Ratio G/HA 0,001 0,004 0,016 0062
POST
〔16〕????20????20????80????90
〔15〕????70????80????100????100
〔14〕????-????60????80????100
〔5〕????0????0????30????40
〔19〕????20????30????40????60
〔20〕????20????30????40????60
〔11〕????60????60????90????100
〔3〕????50????100????100????100
〔1〕????20????30????90????100
〔10〕????60????80????90????100
〔6〕????60????100????100????100
〔7〕????0????40????60????80
〔21〕????-????60????60????80
〔8〕????0????30????60????100
〔22〕????30????60????90????100
〔23〕????20????90????100????100
〔4〕????20????30????80????90
〔9〕????-????20????50????70
〔24〕????70????70????80????90
〔25〕????60????100????100????100
〔26〕????80????100????100????100
〔17〕????0????40????60????90
〔27〕????30????50????80????90
〔13〕????40????60????80????100
〔28〕????0????50????50????90
〔30〕????30????60????90????100
Table B(is continuous)
CMPD????60
Ratio G/HA 0,004 0,016 0,062 0250
PRE
〔15〕????30????40????80????100
〔14〕????-????90????90????90
〔5〕????60????60????70????80
〔19〕????50????70????90????90
〔20〕????0????50????70????80
〔11〕????90????90????100????100
〔3〕????0????50????60????90
〔1〕????0????50????90????90
〔10〕????30????60????90????100
〔6〕????20????100????100????100
〔7〕????-????30????50????70
〔21〕????20????80????90????100
〔8〕????30????40????60????90
〔22〕????50????80????90????90
〔23〕????70????80????100????100
〔4〕????0????80????90????100
〔9〕????0????20????30????40
〔24〕????50????70????80????90
〔25〕????-????80????100????100
〔26〕????-????90????90????100
〔17〕????20????30????30????90
〔27〕????0????70????100????100
〔13〕????30????70????100????100
〔28〕????30????50????90????100
〔30〕????-????100????100????100
Table B(is continuous)
CMPD????60
Ratio G/HA 0,001 0,004 0,016 0062
POST
〔16〕????-????30????50????80
〔15〕????70????80????100????100
〔14〕????-????70????90????100
〔5〕????0????0????30????50
〔19〕????50????60????70????80
〔20〕????0????30????60????90
〔11〕????30????50????70????90
〔3〕????70????80????90????100
〔1〕????30????50????70????90
〔10〕????-????90????100????100
〔6〕????30????50????80????100
〔7〕????-????0????30????60
〔21〕????50????70????90????100
〔8〕????-????30????50????70
〔22〕????50????70????100????100
〔23〕????30????50????70????90
〔4〕????70????100????100????100
〔9〕????-????0????20????60
〔24〕????-????60????80????90
〔25〕????-????50????70????90
〔26〕????-????100????100????100
〔17〕????-????30????50????70
〔27〕????0????30????50????70
〔13〕????-????30????50????70
〔28〕????60????70????80????90
〔30〕????-????50????70????90
Table B(is continuous)
CMPD????64
Ratio G/HA 0,004 0,016 0,062 0250
PRE
〔16〕????0????50????70????90
〔15〕????50????70????90????100
〔14〕????80????90????100????100
〔5〕????0????30????50????70
〔19〕????30????50????70????90
〔20〕????30????50????70????90
〔11〕????50????70????100????100
〔3〕????50????70????80????90
〔1〕????30????50????70????90
〔10〕????30????60????80????90
〔6〕????30????50????70????90
〔7〕????0????30????50????70
〔21〕????50????80????90????100
〔8〕????30????50????70????90
〔22〕????30????50????70????90
〔23〕????30????50????70????90
〔4〕????80????90????100????100
〔9〕????0????30????60????90
〔24〕????70????80????90????95
〔25〕????30????70????80????90
〔26〕????80????100????100????100
〔17〕????0????30????60????90
〔27〕????30????50????70????90
〔13〕????50????70????80????90
〔28〕????30????50????70????90
〔30〕????30????50????70????90
Table B(is continuous)
CMPD????64
Ratio G/HA 0.25 0,001 0,004 0016
POST
〔16〕????-????100????100????100
〔15〕????60????100????100????100
〔14〕????-????100????100????100
〔5〕????30????60????90????100
〔19〕????0????60????100????100
〔20〕????0????20????80????100
〔11〕????30????100????100????100
〔3〕????50????80????100????100
〔1〕????0????20????30????100
〔10〕????-????100????100????100
〔6〕????60????100????100????100
〔7〕????-????90????100????100
〔21〕????40????90????100????100
〔8〕????-????90????100????100
〔22〕????50????90????100????100
〔23〕????60????100????100????100
〔4〕????30????80????100????100
〔9〕????-????100????100????100
〔24〕????-????80????100????100
〔25〕????-????60????80????90
〔26〕????-????100????100????100
〔17〕????-????70????100????100
〔27〕????70????100????100????100
〔13〕????-????90????90????100
〔28〕????80????100????100????100
〔30〕????-????90????100????100
Table B(is continuous)
CMPD????65
Ratio G/HA 0,001 0,004 0,016 0062
PRE
〔16〕????0????20????100????100
〔15〕????0????20????80????90
〔14〕????70????90????100????100
〔5〕????20????60????90????90
〔19〕????20????50????100????100
〔20〕????0????30????100????100
〔11〕????0????20????100????100
〔3〕????0????20????90????100
〔1〕????0????20????80????100
〔10〕????0????0????30????50
〔6〕????0????30????40????50
〔7〕????20????40????80????100
〔21〕????0????30????100????100
〔8〕????0????60????80????100
〔22〕????0????50????90????100
〔23〕????0????30????90????90
〔4〕????0????30????90????90
〔9〕????0????0????90????90
〔24〕????80????100????100????100
〔25〕????40????50????90????100
〔26〕????70????100????100????100
〔17〕????20????40????80????100
〔27〕????0????20????100????100
〔13〕????70????80????100????100
〔28〕????20????40????100????100
〔30〕????70????90????100????100
Table B(is continuous)
CMPD????65
Ratio G/HA 0.25 0,001 0,004 0016
POST
〔16〕????-????50????100????100
〔15〕????20????70????90????100
〔14〕????-????50????100????100
〔5〕????0????40????60????100
〔19〕????0????30????70????90
〔20〕????0????60????90????100
〔11〕????20????40????90????100
〔3〕????0????30????90????100
〔1〕????0????0????30????40
〔10〕????-????80????100????100
〔6〕????30????80????100????100
〔7〕????-????80????90????100
〔21〕????20????40????90????100
〔8〕????-????80????90????100
〔22〕????0????30????90????100
〔23〕????40????60????80????100
〔4〕????0????20????40????100
〔9〕????-????50????90????100
〔24〕????-????30????50????80
〔25〕????-????30????40????90
〔26〕????-????90????100????100
〔17〕????-????40????80????100
〔27〕????0????50????90????100
〔13〕????-????60????90????90
〔28〕????50????60????90????100
〔30〕????-????50????90????100
Table B(is continuous)
CMPD????66
Ratio G/HA 0,001 0,004 0,016 0062
PRE
〔16〕????20????40????70????90
〔15〕????0????0????40????60
〔14〕????40????60????100????100
〔5〕????20????70????100????100
〔19〕????20????30????90????90
〔20〕????20????20????40????80
〔11〕????0????20????60????100
〔3〕????0????0????20????80
〔1〕????0????0????0????0
〔10〕????0????0????30????80
〔6〕????0????0????20????30
〔7〕????20????30????40????90
〔21〕????0????20????90????90
〔8〕????0????30????90????100
〔22〕????20????40????80????100
〔23〕????0????0????30????70
〔4〕????0????20????40????80
〔9〕????0????0????50????70
〔24〕????0????40????100????100
〔25〕????30????50????90????100
〔26〕????40????60????90????100
〔17〕????0????30????60????90
〔27〕????0????20????90????100
〔13〕????60????70????100????100
〔28〕????0????0????20????80
〔30〕????70????80????90????100
Table B(is continuous)
CMPD????66
Ratio G/HA 0,001 0,004 0,016 0062
POST
〔16〕????0????30????100????100
〔15〕????50????80????90????100
〔14〕????-????100????100????100
〔5〕????30????40????80????100
〔19〕????30????70????90????100
〔20〕????70????100????100????100
〔11〕????30????80????100????100
〔3〕????40????60????100????100
〔1〕????0????40????80????100
〔10〕????-????90????100????100
〔6〕????90????100????100????100
〔7〕????-????30????80????90
〔21〕????60????90????100????100
〔8〕????-????30????40????70
〔22〕????30????100????100????100
〔23〕????80????100????100????100
〔4〕????30????80????90????100
〔9〕????-????80????100????100
〔24〕????-????60????80????100
〔25〕????-????80????90????90
〔26〕????-????100????100????100
〔17〕????-????40????80????90
〔27〕????20????40????70????90
〔13〕????-????80????90????100
〔28〕????80????100????100????100
〔30〕????-????60????90????100
Table B(is continuous)
CMPD????67
Ratio G/HA 0,001 0,004 0,016 0062
PRE
〔16〕????20????40????100????100
〔15〕????0????30????70????100
〔14〕????60????70????100????100
〔5〕????30????70????100????100
〔19〕????0????20????70????80
〔20〕????0????40????100????100
〔11〕????20????50????100????100
〔3〕????0????20????70????80
〔1〕????-????0????20????90
〔10〕????0????0????40????80
〔6〕????0????20????100????100
〔7〕????0????20????30????40
〔21〕????0????20????30????100
〔8〕????0????20????50????90
〔22〕????0????20????30????40
〔23〕????0????30????100????100
〔4〕????20????60????100????100
〔9〕????0????20????80????100
〔24〕????60????90????100????100
〔25〕????30????50????80????90
〔26〕????30????70????100????100
〔17〕????0????20????70????100
〔27〕????0????20????90????100
〔13〕????30????70????80????100
〔28〕????0????30????90????100
〔30〕????30????70????80????90
Table B(is continuous)
CMPD????67
Ratio G/HA 0,001 0,004 0,016 0062
POST
〔16〕????-????90????100????100
〔15〕????40????90????100????100
〔14〕????-????100????100????100
〔5〕????30????70????90????100
〔19〕????20????80????90????90
〔20〕????70????100????100????100
〔11〕????50????90????100????100
〔3〕????40????80????100????100
〔1〕????0????30????80????100
〔10〕????-????100????100????100
〔6〕????60????100????100????100
〔7〕????-????90????100????100
〔21〕????30????80????100????100
〔8〕????-????90????100????100
〔22〕????30????90????100????100
〔23〕????70????90????100????100
〔4〕????20????70????80????100
〔9〕????-????20????90????100
〔24〕????-????70????90????100
〔25〕????-????80????100????100
〔26〕????-????100????100????100
〔17〕????-????90????100????100
〔27〕????40????80????100????100
〔13〕????-????90????100????100
〔28〕????70????90????100????100
〔30〕????-????70????90????100
Annotate:
(19) Radix sidae acutae
(20) thorn apple
(21) pharbitis nilChoisy
(22) senna
(23) Johnson grass
(24) volume stem knotweed
(25) amur foxtail
(26) rape
(27) green green bristlegrass
(28) lamb's-quarters
(29) wild corydalis
(30) chickweed
Test C
After sprouting
(diameter 17cm, dark 15cm) makes plant-growth to the processing stage with 6 circular flowerpots.Four kinds of seeds of each plantation or stem tuber in 4 flowerpots, another manufacturing soybean uses the Sassafras silty loam as growth matrix.The 6th flowerpot Tama silt loam maize planting.During spraying, the soil in this basin temporarily covers with perlite, removes after having sprayed again, and observed any effect is only absorbed from blade.Another corn flowerpot (diameter 25.5cm, dark 19.5cm) that is grown in the Sassafras silty loam is also included, to measure the influence of blade/soil treatment to plant-growth.Plant-growth 10-20 days,, after sprouting, spray with compound of the present invention 2-5 leaf phase.Included plant is as follows: G4646 corn, WILLIAMS-DARLING Ton soybean, green green bristlegrass, Herba Setariae viridis, foreign wild broomcorn millet, lady's-grass, barnyard grass, stone thatch Chinese sorghum, G522 Chinese sorghum, Rhizoma Cyperi, piemarker, Siberian cocklebur, water pepper (Polygonum persicaria) lamb's-quarters Amaranthus retroflexus (Amaranthus retroflexus), pharbitis nilChoisy (Ipo moea hederacea), thorn apple, artemisiifolia (Ambrosia artemisiifolia).
Before sprouting
Plant as above-mentioned, just all use the Tama silt loam.Carried out, and then all flowerpots were watered in second day that is sprayed at before the sprouting of compound after the plantation with the imitation rainfall.
After the processing, all plants kept in the greenhouse about 20 days, then with estimating the plant reaction classification.Classification is based on 0 to 100 scale, and 0=does not have effect, and 100=suppresses fully.Each level of reaction is shown among the table C.
Table C(is continuous)
CMPD????60
Ratio GH/HA 0,016 0,032 0,064 0125
PRE
Soil type TAM TAM TAM TAM
〔9〕????0????0????0????0
〔10〕????30????40????60????85
〔27〕????20????25????35????60
〔16〕????20????20????30????40
〔31〕????70????80????95????100
〔5〕????0????0????20????-
〔6〕????65????70????90????100
70????90????100????100
(12)??75????100????100????100
〔4〕????35????60????80????-
〔15〕????0????0????0????-
〔3〕????0????0????0????-
〔32〕????50????65????95????-
〔28〕????25????40????60????-
〔33〕????50????60????90????-
〔21〕????0????0????0????-
〔20〕????0????0????0????-
Table C(is continuous)
CMPD????92
Ratio GM/HA 0,016 0,032 0,064 0125
PRE
Soil type TAM TAM TAM TAM
〔9〕????0????0????0????0
〔10〕????0????25????50????80
〔27〕????0????35????70????100
〔16〕????0????30????70????95
〔31〕????20????45????85????95
〔5〕????0????20????40????70
〔6〕????25????45????85????100
〔23〕????50????65????100????100
〔12〕????45????55????90????100
〔4〕????0????25????65????80
〔15〕????0????0????0????30
〔3〕????0????0????0????20
〔32〕????30????60????95????100
〔28〕????20????40????90????100
〔33〕????50????70????100????100
〔21〕????0????0????0????25
〔20〕????0????0????0????35
CMPD????92
Ratio GM/HA 0,002 0,004 0,008 0,016 0,032 0,064 0125
POST
Soil type SAS SAS SAS SAS SAS SAS SAS
〔9〕????0????0????0????0????20????35????60
〔10〕????65????85????100????100????100????100????100
〔27〕????40????60????80????90????95????100????100
〔16〕????40????65????80????100????100????100????100
〔31〕????0????40????80????95????100????100????100
〔5〕????0????0????0????25????40????50????80
〔6〕????0????30????50????70????100????100????100
〔23〕????80????95????100????100????100????100????100
〔12〕????85????95????100????100????100????100????100
Table C(is continuous)
Ratio GM/HA 0,002 0,004 0,008 0,016 0,032 0,064 0125
POST
Soil type SAS SAS SAS SAS SAS SAS SAS
〔4〕????0????35????60????90????100????100????100
〔15〕????0????25????40????65????85????95????100
〔3〕????35????60????90????100????100????100????100
〔32〕????25????40????50????60????70????85????95
〔28〕????40????65????85????95????100????100????100
〔33〕????75????95????100????100????100????100????100
〔21〕????0????30????55????70????85????95????100
〔20〕????0????0????20????40????60????70????85
〔34〕????0????0????0????0????0????20????40
Table C(is continuous)
CMPD????96
Ratio GM/HA 0,016 0,032 0,064 0,125 0250
PRE
Soil type TAM TAM TAM TAM TAM
〔9〕????0????0????0????0????0
〔10〕????0????0????0????20????45
〔27〕????0????15????20????35????50
〔16〕????0????15????20????35????50
〔31〕????0????0????0????0????15
〔5〕????0????0????0????0????15
〔6〕????0????15????30????70????85
〔23〕????0????20????45????55????75
〔12〕????20????35????55????75????95
〔4〕????0????0????0????0????0
〔15〕????0????0????20????30????40
〔3〕????0????10????20????35????50
〔32〕????15????35????50????60????75
〔28〕????0????0????0????15????25
〔33〕????0????25????45????65????85
〔21〕????0????0????0????0????0
〔20〕????0????0????0????15????20
Table C(is continuous)
CMPD????96
Ratio GM/HA 0,002 0,004 0,008 0,016 0,032 0064
POST
Soil type SAS SAS SAS SAS SAS SAS
〔9〕????0????20????50????60????80????90
〔10〕????90????90????98????98????100????100
〔27〕????50????60????70????70????90????98
〔16〕????40????50????60????70????98????100
〔5〕????0????0????0????20????40????50
〔6〕????70????98????100????100????100????100
〔23〕????60????98????100????100????100????100
〔12〕????80????90????98????100????100????100
〔4〕????0????0????0????0????30????70
〔15〕????0????0????30????50????60????90
〔3〕????30????70????80????90????100????100
〔32〕????20????30????30????50????70????98
〔28〕????0????0????30????30????30????30
〔33〕????0????0????40????40????80????90
〔21〕????0????30????30????30????40????50
〔20〕????40????60????60????60????100????100
〔34〕????20????20????30????60????60????90
Table C(is continuous)
CMPD????100
Ratio GM/HA 0,016 0,032 0,064 0,125 0250
PRE
Soil type TAM TAM TAM TAM TAM
〔9〕????0????0????0????0????20
〔10〕????0????25????40????70????80
〔27〕????25????45????85????95????100
〔16〕????0????35????70????95????100
〔31〕????40????85????100????100????100
〔5〕????0????20????35????50????65
〔6〕????35????60????100????100????100
Table C(is continuous)
Ratio GM/HA 0,016 0,032 0,064 0,125 0250
PRE
Soil type TAM TAM TAM TAM TAM
〔23〕????70????90????100????100????100
〔12〕????75????95????100????100????100
〔4〕????30????50????70????90????100
〔15〕????0????0????0????0????25
〔3〕????0????0????20????35????50
〔32〕????40????70????95????100????100
〔28〕????25????40????65????95????100
〔33〕????30????65????90????100????100
〔21〕????0????0????0????0????35
〔20〕????0????0????30????45????70
CMPD????100
Ratio GM/HA 0,002 0,004 0,008 0,016 0,032 0,064 0125
POST
Soil type SAS SAS SAS SAS SAS SAS SAS
〔9〕????0????0????0????0????0????0????30
〔10〕????65????75????90????100????100????100????100
〔27〕????50????65????80????95????100????100????100
〔16〕????45????60????80????90????95????100????100
〔31〕????50????65????80????95????95????100????100
〔5〕????0????0????0????30????40????50????80
〔6〕????50????60????70????80????100????100????100
〔23〕????95????100????100????100????100????100????100
〔12〕????100????100????100????100????100????100????100
〔4〕????0????20????40????65????85????90????95
〔15〕????0????40????70????80????90????100????100
〔3〕????45????95????100????100????100????100????100
〔32〕????0????20????45????60????70????95????100
〔28〕????30????40????60????80????90????100????100
〔33〕????65????90????100????100????100????100????100
〔21〕????30????70????85????100????100????100????100
〔20〕????0????0????0????0????25????45????70
〔34〕????0????0????0????0????0????0????20
Annotate:
(31) foreign wild lamb's-quarters
(32) water pepper
(33) Amaranthus retroflexus
(34) corn that covers with perlite of flowerpot
" SAS " is the Sassafras sandy loam, and " TAM " is the Tama silt loam.Test D
In the plastic flowerpot of 20cm, with Metro350 matrix plantation potato (Solanum tuberosum, " Green Mountain " Cultivar).When potato 17 ages in days, spray.In the 25cm of plastic lining flowerpot, with Sassafras silty loam (pH6.5,1% organic substance) plantation barnyard grass, stone thatch Chinese sorghum, Herba Setariae viridis, lady's-grass, Rhizoma Cyperi, thorn apple, piemarker, Siberian cocklebur and pharbitis nilChoisy etc.These plants are sprayed when 9 ages in days.
With 62,16,4 and 1g/ha atomization compound.Compound is sprayed on the flowerpot that the potato plant is housed with each ratio, also is sprayed on simultaneously on the flowerpot that other plant is housed.Compound is dissolved in the solvent of non-plant toxicity, and content is 4.0%, sprays with 374L/ha.This plant remains in the greenhouse, sprays and estimates in back 11 days.
Injury to all spraying plants is compared with control plant and is made an appraisal.Extent of injury is definite to estimate, and with 0 to 100% as scale, 0=does not have effect, and 100=suppresses fully.The results are shown among the table D.
Table D compound 21
Usage ratio (g/ha)
Plant 62 16 41
Potato 0000
Barnyard grass 100 100 70 30
Stone thatch Chinese sorghum 100 100 100 60
Herba Setariae viridis 100 100 90 60
Lady's-grass 90 85 60 50
Rhizoma Cyperi 90 90 80 30
Thorn apple 80 60 40 20
Piemarker 100 95 50 20
Siberian cocklebur 90 50 30 0
Pharbitis nilChoisy 90 70 40 20 test E
In the 10cm plastic flowerpot, with Metro350 matrix plantation tomato (Lycopersicon esculentum, Rutgers Cultivar) and capsicum (Capsicum frutescens, Yolo Cultivar).Tomato and capsicum are sprayed when 19 ages in days.In the 25cm of plastic lining flowerpot, with Sassafras silty loam (pH6.5,1% organic substance) plantation Rhizoma Cyperi, lady's-grass, senna, Radix sidae acutae, thorn apple, piemarker, lamb's-quarters, green green bristlegrass, Siberian cocklebur, pharbitis nilChoisy, stone thatch Chinese sorghum, barnyard grass, Herba Setariae viridis, volume stem knotweed, downy brome (Bromustectorum), wild avena sativa, chickweed and amur foxtail.These plants are sprayed when the 7-11 age in days.
With 62,16,4 and 1g/ha atomization compound.With compound with on the flowerpot that each ratio is sprayed on the flowerpot that tomato is housed, is equipped with capsicum and on three flowerpots that other kind of plant are housed.Compound is dissolved in the solvent of non-plant toxicity, sprays with 374L/ha.This plant remains in the greenhouse, sprays and estimates after 16 days
The injury of all spraying plants is compared with control plant and made an appraisal.Extent of injury is definite to estimate, and as scale, 0=does not have effect with 0-100%, and 100=suppresses fully.The results are shown among the table E.
Table E compound 21
Usage ratio (g/ha)
Plant 62 16 41
Tomato 10 000
Capsicum 80 70 50 30
Rhizoma Cyperi 100 100 30 0
Lady's-grass 90 80 50 30
Senna 100 100 90 40
Radix sidae acutae 100 100 50 20
Thorn apple 100 50 10 0
Piemarker 100 100 70 50
Lamb's-quarters 60 50 40 0
Green green bristlegrass 100 100 100 50
Siberian cocklebur 100 80 50 20
Pharbitis nilChoisy 90 85 50 20
Stone thatch Chinese sorghum 100 100 100 50
Barnyard grass 100 100 100 40
Herba Setariae viridis 100 100 90 40
Volume stem knotweed 100 90 90 40
Downy brome 100 100 80 20
Wild avena sativa 100 70 30 20
Chickweed 100 100 90 90
Amur foxtail 100 100 100 70
Claims (44)
1, a kind of compound that from formula I, chooses and be applicable to the agricultural salt.
Wherein
J is
R is H or CH
3
W is O or S;
R
1Be Rf or Rg;
R
fBe H, C
1-C
3Alkyl, C
1-C
3Haloalkyl, halogen, NO
2, C
1-C
3Alkoxyl group, C
1-C
3Alkylthio or CN;
R
8Be C
1-C
3Haloalkyl, C
2-C
3Alkyl, cyclopropyl, by C
1-C
3Alkoxyl group, OH, C
1-C
2The C that alkylthio or CN replace
1-C
3Alkyl, CN, W
2R
11, amino, C
1-C
3Alkylamino or C
1-C
3Dialkyl amido;
R
2Be C
1-C
4Alkyl sulphinyl, C
1-C
4Alkyl sulphonyl, C
3-C
5Cycloalkyl sulfo-, C
3-C
5Cycloalkyl sulfinyl, C
3-C
5Naphthene sulfamide base, SO
2NH
2, SO
2NRdRe, SO
2NR
7R
8, SO
2NR
7' R
8, OSO
2R
8, SO
2OR
8, N3, P (W
1) (OC
1-C
2Alkyl)
2, CN, CO
2R
9, CO
2R
9', CH
2F, CF
2H, CH
2Cl, CCl
2H or C
2-C
4Haloalkyl;
R
3Be C
1-C
4Alkyl sulphinyl, C
3-C
5Cycloalkyl sulfo-, C
3-C
5Cycloalkyl sulfinyl, C
3-C
4Naphthene sulfamide base, SO
2NH
2, SO
2NRdRe, SO
2NR
7R
8, SO
2NR
7' R
8, OSO
2R
8, SO
2OR
8, N
3, P (W
1) (OC
1-C
2Alkyl)
2, CN, CO
2R
9, CO
2R
9' or C
1-C
4Haloalkyl;
R
4Be C
1-C
4Alkyl sulphinyl, C
3-C
5Cycloalkyl sulfo-, C
3-C
5Cycloalkyl sulfinyl, C
3-C
4Naphthene sulfamide base, SO
2NH
2, SO
2NRdRe, SO
2NR
7R
8, OSO
2R
8, SO
2OR
8, N
3, P (W
1) (OC
1-C
2Alkyl)
2, CN, CO
2R
9Or C
1-C
4Haloalkyl;
R
5Be C
1-C
4Alkyl sulphinyl, C
1-C
4Alkyl sulphonyl, C
3-C
5Cycloalkyl sulfo-, C
3-C
5Cycloalkyl sulfinyl, C
3-C
5Naphthene sulfamide base, SO
2NH
2, SO
2NRd Re, SO
2NR
7R
8, OSO
2R
8, SO
2OR
8, N
3, P (W
1) (OC
1-C
2Alkyl)
2, CN, CO
2R
9Or C
1-C
4Haloalkyl;
R
6Be C
1-C
4Alkylthio, C
1-C
4Alkyl sulphinyl, C
1-C
4Haloalkyl thio, C
1-C
4Haloalkyl sulfinyl, C
1-C
4Halogenated alkyl sulfonyl, C
3-C
4Alkenyl sulfo-, C
3-C
4Alkenyl sulfinyl, C
3-C
4Alkenyl alkylsulfonyl, C
3-C
4Alkynyl sulfo-, C
3-C
4Alkynyl sulfinyl, C
3-C
4Alkynyl alkylsulfonyl, C
3-C
5Cycloalkyl sulfo-, C
3-C
5Cycloalkyl sulfinyl, C
3-C
5Naphthene sulfamide base, SO
2NRd Re, SO
2NR
7R
8, OSO
2R
8, SO
2OR
8, N
3, P (W
1) (OC
1-C
2Alkyl)
2, CN, CO
2R
9Or C
1-C
4Haloalkyl;
R
7Be H, C
2-C
3Cyano group alkyl, C
3-C
4Alkenyl or C
3-C
4Alkynyl;
R
' 7Be C
1-C
4Alkyl;
R
8Be C
1-C
4Alkyl, C
1-C
4Haloalkyl, C
3-C
4Alkenyl, C
3-C
4Alkynyl, C
2-C
4Alkoxyalkyl or cyclopropyl; Perhaps
R
7And R
8Can link up becomes-(CH
2)
3-,-(CH
2)
4-,-(CH
2)
5-or-CH
2CH
2O CH
2CH
2-;
R
9Be CH
2CH
2R
10, CH
2CRF
3, C
3-C
4Haloalkyl, C
3-C
4Alkynyl, C
2-C
4Alkyl-thio-alkyl, C
3-C
5Cycloalkyl or C
4-C
7Cycloalkylalkyl;
R
' 9Be C
1-C
4Alkyl, C
3-C
4Alkenyl, CH
2CH
2Cl, CH
2CH
2Br, CH
2CH
2OCH
3Or CH
2CH
2OC
2H
5
R
10Be OH, F, CN, OSO
2(C
1-C
3Alkyl) or OSO
2(C
1-C
3Haloalkyl);
R
11Be C
1-C
3Alkyl, C
1-C
3Haloalkyl, C
3-C
4Alkenyl or C
3-C
4Alkynyl;
W
1Be O or S;
W
2Be O or S;
A is
X is H, C
1-C
4Alkyl, C
1-C
4Alkoxyl group, C
2-C
4Halogenated alkoxy, C
1-C
4Haloalkyl, C
2-C
4Haloalkyl thio, C
1-C
4Alkylthio, halogen, C
2-C
5Alkoxyalkyl, C
2-C
5Alkoxyl group alkoxyl group, amino, C
1-C
3Alkylamino or two (C
1-C
3Alkyl) amino;
Y is H, C
1-C
4Alkyl, C
1-C
4Alkoxyl group, C
2-C
4Halogenated alkoxy, C
2-C
4Haloalkyl thio, C
1-C
4Alkylthio, C
2-C
5Alkoxyalkyl, C
2-C
5Alkoxyl group alkoxyl group, amino, C
1-C
3Alkylamino, two (C
1-C
3Alkyl) amino, C
3-C
4Alkenyloxy, C
3-C
4Alkynyloxy group, C
2-C
5Alkyl-thio-alkyl, C
2-C
5Alkyl sulphinyl alkyl, C
2-C
5Alkyl sulphonyl alkyl, C
1-C
4Haloalkyl, C
2-C
4Alkynyl, C
3-C
5Cycloalkyl, azido-,
Or N (OCH
3) CH
3
M is 2 or 3;
Q
1And Q
2Be respectively O or S;
Ra is H or C
1-C
3Alkyl;
Rb and Rc are respectively C
1-C
3Alkyl;
Rd is H or C
1-C
2Alkyl;
Re is C
1-C
2Alkoxyl group;
Z is CH, N, CCH
3, CC
2H
5, CCl or CBr;
Y
1Be O or CH
2
X
1Be CH
3, OCH
3, OC
2H
5Or OCF
2H;
X
2Be CH
3, C
2H
5Or CH
2CF
3
Y
2Be OCH
3, OC
2H
5, SCH
3, SC
2H
5, CH
3Or CH
2CH
3
X
3Be CH
3Or OCH
3
Y
3Be H or CH
3
X
4Be CH
3, OCH
3, OC
2H
5, CH
2O CH
3Or Cl;
Y
4Be CH
3, OCH
3, OC
2H
5Or Cl;
Suppose
1) if X is a halogen, then Z is CH, and Y is OCH
3, OC
2H
5, NH
2, NHCH
3, N (CH
3)
2Or N (OCH
3) CH
3
2) if W is S, then R is H, and A is A-1, and Z is CH or N, and Y is CH
3, OCH
3, OC
2H
5, CH
2OCH
3, C
2H
5, CF
3, SCH
3, OCH
2CH=CH
2, OCH
2C ≡ CH,
3) if the total carbon atom number of X and Y greater than 4, R then
1, R
2, R
3, R
4, R
5Or R
6Carbon atom amount to and to be less than or equal to 6;
4) if J is J-1, R
2Be C
1-C
4Alkyl sulphonyl, SO
2NRd Re, SO
2NR
' 7R
8Or CO
2R
' 9, or if J is J-2 and R
3Be CF
3, SO
2NRd Re, SO
2NR
' 7R
8Or CO
2R
' 9, then Y is not C
2-C
3Alkyl-thio-alkyl, C
2-C
5Alkyl sulphinyl alkyl, C
2-C
5The alkyl sulphonyl alkyl,
5) if J is J-2 or J-3 and R
3Or R
4Be C
1-C
4Alkyl sulphinyl, then X and Y are not NH
2Or NHCH
3
6) if J is J-2 and R
3Be C
1-C
4Alkyl sulphinyl or SO
2NRd Re, or R
7Be H, then X and Y are not C
2-C
4Halogenated alkoxy;
7) if J is J-5, R then
7Not H and R
6Not SO
2NRd Re;
8) if J is J-2 and R
3Be SO
2NH
2Or SO
2NRd Re, or R
7Be H, then X is not an iodine;
9) if J is J-2 and R
7Be H and or R
3Be SO
2NRd Re, then Y is not C
2-C
4Alkynyl;
10) X
4And Y
4Not C1 simultaneously;
11) if J is J-1, J-2, J-3, J-4 and A is A-5, then Rf is not H;
12) if J is J-1 or J-2, then A is not A-6;
13) if J is J-1 and A is A-7, R then
2Not C
1-C
4Alkyl sulphonyl;
14) if R
2Or R
3Be CO
2R
' 9Or SO
2NR
' 7R
8, R then
1Be Rg; If R
2Or R
3Not CO
2R
' 9Or SO
2NR
' 7R
8, R then
1Be Rf;
15) if J is J-2 and R
1Be adjacent to the sulfonylurea bridged bond, then Rg is C
1-C
3Haloalkyl, C
2-C
3Alkyl, cyclopropyl, CN, W
2R
11, amino, C
1-C
3Alkylamino or C
1-C
3Dialkyl amido.
2, a kind of compound of claim 1, wherein
X is C
1-C
2Alkyl, C
1-C
2Alkoxyl group, Cl, F, Br, I, CH
2F, CF
3, OCH
2CH
2F, OCH
2CHF
2, OCH
2CF
3, CH
2Cl or CH
2Br;
Y is H, C
1-C
2Alkyl, C
1-C
2Alkoxyl group, CH
2OCH
3, CH
2OCH
2CH
3, NHCH
3, N(OCH
3) CH
3, N(CH
3)
2, CF
3, SCH
3, OCH
2CH=CH
2, OCH
2C ≡ CH, OCH
2CH
2OCH
3,
CH
2SCH
3, cyclopropyl, C ≡ CH or C ≡ CCH
3;
Ra is H or CH
3;
Z is CH or N.
3, a kind of compound of claim 2, wherein
W is O;
Rf is H, CH
3, C
1Haloalkyl, halogen or OCH
3;
Rg is C
1-C
2Haloalkyl, ethyl, W
2R
11, CH
2OCH
3, CH
2SCH
3, CH
2CN, C
1-C
2Alkylamino or N(CH
3)
2;
R
2Be C
1-C
4Alkyl sulphinyl, C
1-C
4Alkyl sulphonyl, SO
2NH
2, SO
2NRd Re, SO
2NR
7R
8, SO
2NR
7' R
8, OSO
2R
8, SO
2OR
8, N
3, P(W
1) (OC
1-C
2Alkyl)
2, CN, CO
2R
9, CO
2R
9', CHF
2, CF
2H, CH
2Cl, CCl
2H or C
2-C
4Haloalkyl;
R
3Be C
1-C
4Alkyl sulphinyl, SO
2NH
2, SO
2NRd Re, SO
2R
7R
8, SO
2NR
7' R
8, OSO
2R
8, SO
2OR
8, N
3, P(W
1) (OC
1-C
2Alkyl)
2, CN, CO
2R
9, CO
2R
9' or C
1-C
4Haloalkyl;
R
4Be C
1-C
4Alkyl sulphinyl, SO
2NH
2, SO
2N(OCH
3) CH
3, SO
2NR
7R
8, OSO
2R
8, SO
2OR
8, N
3, P(W
1) (OC
1-C
2Alkyl)
2, CN, CO
2R
9Or C
1-C
4Haloalkyl;
R
5Be C
1-C
4Alkyl sulphinyl, C
1-C
4Alkyl sulphonyl, SO
2NH
2, SO
2N(OCH
3) CH
3, SO
2NR
7R
8, OSO
2R
8, SO
2OR
8, N
3, P(W
1) (OC
1-C
2Alkyl)
2, CN, CO
2R
9Or C
1-C
4Haloalkyl;
R
6Be C
1-C
4Alkylthio, C
1-C
4Alkyl sulphinyl, C
1-C
4Haloalkyl thio, C
1-C
4Haloalkyl sulfinyl, C
1-C
4Halogenated alkyl sulfonyl, C
3-C
4Alkenyl sulfo-, C
3-C
4Alkenyl sulfinyl, C
3-C
4Alkenyl alkylsulfonyl, C
3-C
4Alkynyl sulfo-, C
3-C
4Alkynyl sulfinyl, C
3-C
4Alkynyl alkylsulfonyl, SO
2N(OCH
3) CH
3, SO
2NR
7R
8, OSO
2R
8, SO
2OR
8, N
3, P(W
1) (OC
1-C
2Alkyl)
2, CN, CO
2R
9Or C
1-C
4Haloalkyl;
R
7Be H, C
2-C
3Cyano group alkyl, C
3-C
4Alkenyl or C
3-C
4Alkynyl;
R
8Be C
1-C
4Alkyl, C
1-C
4Haloalkyl, C
3-C
4Alkenyl, C
3-C
4Alkynyl, C
2-C
4Alkoxyalkyl or cyclopropyl;
R
11Be C
1-C
3Alkyl, C
1-C
2Haloalkyl, allyl group or propargyl.
4, a kind of compound of claim 3, wherein J is J-1.
5, a kind of compound of claim 3, wherein J is J-2.
6, a kind of compound of claim 3, wherein J is J-3.
7, a kind of compound of claim 3, wherein J is J-4.
8, a kind of compound of claim 3, wherein J is J-5.
9, a kind of compound of claim 4, wherein
R
7Be H, C
2-C
3Cyano group alkyl, allyl group or propargyl;
R
7' be C
1-C
3Alkyl;
R
8Be C
1-C
3Alkyl, allyl group, propargyl or cyclopropyl;
R
9Be CH
2CH
2R
10, CH
2CH
2SCH
3, propargyl or cyclopropyl methyl;
R
9' be C
1-C
3Alkyl, allyl group, CH
2CH
2OCH
3Or CH
2CH
2Cl;
R
10Be OH, CN or OSO
2CH
3
10, a kind of compound of claim 9, wherein
A is A-1;
X is CH
3, OCH
3, OCH
2CH
3, Cl or OCH
2CF
3;
Y is CH
3, OCH
3, CH
2CH
3, CH
2OCH
3, NHCH
3Or CH(OCH
3)
2
11, a kind of compound of claim 10, wherein Z is CH.
12, a kind of compound of claim 10, wherein Z is N.
13, a kind of compound of claim 5, wherein
R
7Be H, C
2-C
3Cyano group alkyl, allyl group or propargyl;
R
8Be C
1-C
3Alkyl, allyl group, propargyl or cyclopropyl;
14, a kind of compound of claim 13, wherein
A is A-1;
X is CH
3, OCH
3, OCH
2CH
3, Cl or OCH
2CF
3;
Y is CH
3, OCH
3, CH
2CH
3, CH
2OCH
3, NHCH
3Or CH(OCH
3)
2
15, a kind of compound of claim 14, wherein Z is CH.
16, a kind of compound of claim 14, wherein Z is N.
17, a kind of compound of claim 2, wherein
J is J-1;
A is A-1;
Z is CH;
W is O;
R
2Be C
1-C
4Alkyl sulphinyl or C
1-C
4Alkyl sulphonyl;
Rf is H, C
1-C
2Alkyl, C
1Haloalkyl, C
1-C
2Alkoxyl group or C
1-C
2Alkylthio.
18, a kind of compound of claim 17, wherein
Rf is H;
R
2Be C
1-C
4Alkyl sulphonyl;
X is OCH
3;
Y is OCH
3
19, the compound of claim 1, it is N-[(4,6-dimethoxypyridin-2-yl) aminocarboxyl]-3-(1-sulfonyl propyl base)-the 2-Sulphapyridine.
20, the compound of claim 1, it is N-[(4,6-dimethoxypyridin-2-yl) aminocarboxyl]-3-(1-propyl group sulfinyl)-the 2-Sulphapyridine.
21, the compound of claim 1, it is N-[(4,6-dimethoxypyridin-2-yl) aminocarboxyl]-the 3-(ethylsulfonyl)-the 2-Sulphapyridine.
22, the compound of claim 1, it is N2-[(4,6-dimethoxypyridin-2-yl) aminocarboxyl]-N3-ethyl-2,3-pyridine two sulfanilamide (SN).
23, the compound of claim 1, it is N-[(4,6-dimethoxypyridin-2-yl) aminocarboxyl]-3-(sulfonyloxy methyl oxygen base)-the 2-Sulphapyridine.
24, the compound of claim 1, it is N2-[(4,6-dimethoxypyridin-2-yl) aminocarboxyl]-N3-methyl-2,3-pyridine two sulfanilamide (SN).
25, a kind of composition that suppresses undesired plant growth that is applicable to is comprising the compound and at least a following material of a kind of claim 1 of significant quantity: the mixture of tensio-active agent, solid inert diluents or liquid inert diluent and aforementioned substances.
26, a kind of composition that suppresses undesired plant growth that is applicable to is comprising the compound and at least a following material of a kind of claim 2 of significant quantity: the mixture of tensio-active agent, solid inert diluents or liquid inert diluent and aforementioned substances.
27, a kind of composition that suppresses undesired plant growth that is applicable to is comprising the compound and at least a following material of a kind of claim 3 of significant quantity: the mixture of tensio-active agent, solid inert diluents or liquid inert diluent and aforementioned substances.
28, a kind of composition that suppresses undesired plant growth that is applicable to is comprising the compound and at least a following material of a kind of claim 4 of significant quantity: the mixture of tensio-active agent, solid inert diluents or liquid inert diluent and aforementioned substances.
29, a kind of composition that suppresses undesired plant growth that is applicable to is comprising the compound and at least a following material of a kind of claim 5 of significant quantity: the mixture of tensio-active agent, solid inert diluents or liquid inert diluent and aforementioned substances.
30, a kind of composition that suppresses undesired plant growth that is applicable to is comprising the compound and at least a following material of a kind of claim 6 of significant quantity: the mixture of tensio-active agent, solid inert diluents or liquid inert diluent and aforementioned substances.
31, a kind of composition that suppresses undesired plant growth that is applicable to is comprising the compound and at least a following material of a kind of claim 7 of significant quantity: the mixture of tensio-active agent, solid inert diluents or liquid inert diluent and aforementioned substances.
32, a kind of composition that suppresses undesired plant growth that is applicable to is comprising the compound and at least a following material of a kind of claim 8 of significant quantity: the mixture of tensio-active agent, solid inert diluents or liquid inert diluent and aforementioned substances.
33, a kind of method that suppresses undesired plant growth is comprising the compound of using a kind of claim 1 of significant quantity in place to be protected.
34, a kind of method that suppresses undesired plant growth is comprising the compound of using a kind of claim 2 of significant quantity in place to be protected.
35, a kind of method that suppresses undesired plant growth is comprising the compound of using a kind of claim 3 of significant quantity in place to be protected.
36, a kind of method that suppresses undesired plant growth is comprising the compound of using a kind of claim 4 of significant quantity in place to be protected.
37, a kind of method that suppresses undesired plant growth is comprising the compound of using a kind of claim 5 of significant quantity in place to be protected.
38, a kind of method that suppresses undesired plant growth is comprising the compound of using a kind of claim 6 of significant quantity in place to be protected.
39, a kind of method that suppresses undesired plant growth is comprising the compound of using a kind of claim 7 of significant quantity in place to be protected.
40, a kind of method that suppresses undesired plant growth is comprising the compound of using a kind of claim 8 of significant quantity in place to be protected.
41, a kind of method that suppresses undesired plant growth is comprising a kind of compound that is selected from claim 19 to 24 of using significant quantity in place to be protected.
42, a kind of method that suppresses undesired plant growth is comprising a kind of claim 19, compound of 21 or 24 of being selected from of corn crop to be protected being used significant quantity.
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US93942886A | 1986-12-08 | 1986-12-08 | |
US039,491 | 1987-04-16 | ||
US07/090,889 US4808721A (en) | 1987-04-16 | 1987-08-28 | Herbicidal pyridinesulfonylureas |
US090,889 | 1987-08-28 | ||
US07/101,148 US4774337A (en) | 1987-04-16 | 1987-09-25 | Herbicidal pyridinesulfonylureas |
US101,148 | 1987-09-25 | ||
US939,428 | 1987-09-25 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN87107320A true CN87107320A (en) | 1988-12-07 |
CN1023680C CN1023680C (en) | 1994-02-09 |
Family
ID=27376683
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN 87107320 Expired - Lifetime CN1023680C (en) | 1986-12-08 | 1987-12-08 | Herbicide containing mainly pyridine sulfonylurea |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN1023680C (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1044765C (en) * | 1990-01-10 | 1999-08-25 | 赫彻斯特股份公司 | Pyridylsulfonylurea herbicides and agent for regulating plant growth |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106810577B (en) * | 2015-11-30 | 2018-08-07 | 浙江新安化工集团股份有限公司 | One kind glyphosate derivative containing heterocycle and preparation method thereof and application |
-
1987
- 1987-12-08 CN CN 87107320 patent/CN1023680C/en not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1044765C (en) * | 1990-01-10 | 1999-08-25 | 赫彻斯特股份公司 | Pyridylsulfonylurea herbicides and agent for regulating plant growth |
Also Published As
Publication number | Publication date |
---|---|
CN1023680C (en) | 1994-02-09 |
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