SUBSTITUTED-ISOXAZOLINE-CONTAINING AROMATIC COMPOUND, PREPARATION METHOD THEREFOR, HERBICIDAL COMPOSITION AND USE THEREOF

Abstract

The invention belongs to the technical field of pesticides, and specifically relates to a type of substituted-isoxazoline-containing aromatic compound, preparation method therefor, herbicidal composition and use thereof. The compound is as shown in general formula I:

##STR00001##

Wherein, Q represents

##STR00002##

Y represents halogen, halogenated alkyl or cyano; Z represents halogen; X.sub.1, X.sub.2 each independently represent hydrogen, halogen, alkyl, etc.; X.sub.3 represents halogen, cyano, etc.; X.sub.4 each independently represents —COOR.sub.5 or -alkyl-COOR.sub.5; R.sub.5 each independently represents hydrogen, alkyl, etc.. The compound has excellent herbicidal activity against gramineous weeds, broadleaf weeds, and so on even at low application rates, and has high selectivity for crops.

Claims

1. A substituted-isoxazoline-containing aromatic compound, as shown in general formula I: ##STR00749## wherein, Q represents ##STR00750## Y represents halogen, halogenated alkyl or cyano; Z represents halogen; Q.sub.1, Q.sub.2, Q.sub.3, Q.sub.4, Q.sub.5 each independently represent O or S; R.sub.1, R.sub.2, R.sub.6 each independently represent hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl; R.sub.7, R.sub.8 each independently represent hydrogen, alkyl, halogen, halogenated alkyl or amino; X.sub.1, X.sub.2 each independently represent hydrogen, halogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, —OR.sub.3, —(CO)OR.sub.3 or phenyl; wherein, the “alkyl”, “alkenyl”, “alkynyl”, “cycloalkyl” or “cycloalkylalkyl” is each independently unsubstituted or substituted with at least one substituent selected from the group consisting of halogen; X.sub.3 represents halogen, cyano, formyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, —OR.sub.3, —(CO)OR.sub.3, —SR.sub.3, heterocyclyl, heterocyclylalkyl, aryl, arylalkyl or amino, and X.sub.3 does not represent methyl; wherein, the “alkyl”, “alkenyl” or “alkynyl” is each independently unsubstituted or substituted with at least one substituent selected from the group consisting of halogen, cyano, —OR.sub.3, —(CO)R.sub.3, —SR.sub.3, —(SO.sub.2)R.sub.3, —O(CO)R.sub.3, —O—(SO.sub.2)R.sub.3, —(CO)OR.sub.3, —O(CO)OR.sub.3, —O-alkyl-(CO)OR.sub.3 or —O(CO)(CO)OR.sub.3; the “cycloalkyl”, “cycloalkylalkyl”, “heterocyclyl”, “heterocyclylalkyl”, “aryl” or “arylalkyl” is each independently unsubstituted or substituted with at least one substituent selected from the group consisting of oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, halogenated alkyl, halogenated alkenyl, halogenated alkynyl, halogenated cycloalkyl, cycloalkyl substituted with alkyl, —OR.sub.4, —SR.sub.4, —(CO)OR.sub.4, —(SO.sub.2)R.sub.4 or —N(R.sub.4).sub.2; the “amino” is unsubstituted or substituted with one or two substituents selected from the group consisting of —R.sub.3; X.sub.4 each independently represents —COOR.sub.5 or -alkyl-COOR.sub.5; R.sub.3 each independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl; R.sub.4 each independently represents hydrogen, alkyl or halogenated alkyl; R.sub.5 each independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl; wherein, the “alkyl”, “alkenyl”, “alkynyl”, “cycloalkyl” or “cycloalkylalkyl” is each independently unsubstituted or substituted with at least one substituent selected from the group consisting of halogen.

2. The substituted-isoxazoline-containing aromatic compound according to claim 1, which is characterized in that, Y represents halogen, halogenated C1-C8 alkyl or cyano; R.sub.1, R.sub.2, R.sub.6 each independently represent hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl or C3-C8 cycloalkyl C1-C8 alkyl; R.sub.7, R.sub.8 each independently represent hydrogen, C1-C8 alkyl, halogen, halogenated C1-C8 alkyl or amino; X.sub.1, X.sub.2 each independently represent hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, —OR.sub.3, —(CO)OR.sub.3 or phenyl; wherein, the “C1-C8 alkyl”, “C2-C8 alkenyl”, “C2-C8 alkynyl”, “C3-C8 cycloalkyl” or “C3-C8 cycloalkyl C1-C8 alkyl” is each independently unsubstituted or substituted with at least one substituent selected from the group consisting of halogen; X.sub.3 represents halogen, cyano, formyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, —OR.sub.3, —(CO)OR.sub.3, —SR.sub.3, heterocyclyl, heterocyclyl C1-C8 alkyl, aryl, aryl C1-C8 alkyl or amino; wherein, the “C1-C8 alkyl”, “C2-C8 alkenyl” or “C2-C8 alkynyl” is each independently unsubstituted or substituted with at least one substituent selected from the group consisting of halogen, cyano, —OR.sub.3, —(CO)R.sub.3, —SR.sub.3, —(SO.sub.2)R.sub.3, —O(CO)R.sub.3, —O—(SO.sub.2)R.sub.3, —(CO)OR.sub.3, —O(CO)OR.sub.3, —O—(C1-C8 alkyl)-(CO)OR.sub.3 or —O(CO)(CO)OR.sub.3; the “C3-C8 cycloalkyl”, “C3-C8 cycloalkyl C1-C8 alkyl”, “heterocyclyl”, “heterocyclyl C1-C8 alkyl”, “aryl” or “aryl C1-C8 alkyl” is each independently unsubstituted or substituted with at least one substituent selected from the group consisting of oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 alkynyl, halogenated C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, —OR.sub.4, —SR.sub.4, —(CO)OR.sub.4, —(SO.sub.2)R.sub.4 or —N(R.sub.4).sub.2; the “amino” is unsubstituted or substituted with one or two substituents selected from the group consisting of —R.sub.3; X.sub.4 each independently represents —COOR.sub.5 or -(C1-C8 alkyl)-COOR.sub.5; R.sub.3 each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl or C3-C8 cycloalkyl C1-C8 alkyl; R.sub.4 each independently represents hydrogen, C1-C8 alkyl or halogenated C1-C8 alkyl; R.sub.5 each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl or C3-C8 cycloalkyl C1-C8 alkyl; wherein, the “C1-C8 alkyl”, “C2-C8 alkenyl”, “C2-C8 alkynyl”, “C3-C8 cycloalkyl” or “C3-C8 cycloalkyl C1-C8 alkyl” is each independently unsubstituted or substituted with at least one substituent selected from the group consisting of halogen.

3. The substituted-isoxazoline-containing aromatic compound according to claim 1, which is characterized in that, Y represents halogen, halogenated C1-C6 alkyl or cyano; R.sub.1, R.sub.2, R.sub.6 each independently represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl or C3-C6 cycloalkyl C1-C6 alkyl; R.sub.7, R.sub.8 each independently represent hydrogen, C1-C6 alkyl, halogen, halogenated C1-C6 alkyl or amino; X.sub.1, X.sub.2 each independently represent hydrogen, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, —OR.sub.3, —(CO)OR.sub.3 or phenyl; wherein, the “C1-C6 alkyl”, “C2-C6 alkenyl”, “C2-C6 alkynyl”, “C3-C6 cycloalkyl” or “C3-C6 cycloalkyl C1-C6 alkyl” is each independently unsubstituted or substituted with at least one substituent selected from the group consisting of halogen; X.sub.3 represents halogen, cyano, formyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, —OR.sub.3, —(CO)OR.sub.3, —SR.sub.3, heterocyclyl, heterocyclyl C.sub.1-C.sub.6 alkyl, aryl, aryl C.sub.1-C.sub.6 alkyl or amino; wherein, the “C1-C6 alkyl”, “C2-C6 alkenyl” or “C2-C6 alkynyl” is each independently unsubstituted or substituted with at least one substituent selected from the group consisting of halogen, cyano, —OR.sub.3, —(CO)R.sub.3, —SR.sub.3, —(SO.sub.2)R.sub.3, —O(CO)R.sub.3, —O—(SO.sub.2)R.sub.3, —(CO)OR.sub.3, —O(CO)OR.sub.3, —O—(C1-C6 alkyl)-(CO)OR.sub.3 or —O(CO)(CO)OR.sub.3; the “C3-C6 cycloalkyl”, “C3-C6 cycloalkyl C1-C6 alkyl”, “heterocyclyl”, “heterocyclyl C1-C6 alkyl”, “aryl” or “aryl C1-C6 alkyl” is each independently unsubstituted or substituted with at least one substituent selected from the group consisting of oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, —OR.sub.4, —SR.sub.4, —(CO)OR.sub.4, —(SO.sub.2)R.sub.4 or —N(R.sub.4).sub.2; the “amino” is unsubstituted or substituted with one or two substituents selected from the group consisting of —R.sub.3; X.sub.4 each independently represents —COOR.sub.5 or -(C1-C6 alkyl)-COOR.sub.5; R.sub.3 each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl or C3-C6 cycloalkyl C1-C6 alkyl; R.sub.4 each independently represents hydrogen, C1-C6 alkyl or halogenated C1-C6 alkyl; R.sub.5 each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl or C3-C6 cycloalkyl C1-C6 alkyl; wherein, the “C1-C6 alkyl”, “C2-C6 alkenyl”, “C2-C6 alkynyl”, “C3-C6 cycloalkyl” or “C3-C6 cycloalkyl C1-C6 alkyl” is each independently unsubstituted or substituted with at least one substituent selected from the group consisting of halogen.

4. The substituted-isoxazoline-containing aromatic compound according to claim 1, which is characterized in that, Y represents halogen; R.sub.1, R.sub.2, R.sub.6 each independently represent C1-C6 alkyl; R.sub.7, R.sub.8 each independently represent hydrogen or halogenated C1-C6 alkyl; X.sub.1, X.sub.2 each independently represent hydrogen; X.sub.3 represents halogen, formyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, —OR.sub.3, phenyl or benzyl; wherein, the “C1-C6 alkyl”, “C2-C6 alkenyl” or “C2-C6 alkynyl” is each independently unsubstituted or substituted with one, two or three substituents selected from the group consisting of halogen, —OR.sub.3, —(CO)R.sub.3, —O(CO)R.sub.3, —O—(C1-C3 alkyl)-(CO)OR.sub.3 or —O(CO)(CO)OR.sub.3; the “C3-C6 cycloalkyl”, “C3-C6 cycloalkyl C1-C3 alkyl”, “phenyl” or “benzyl” is each independently unsubstituted or substituted with one, two or three substituents selected from the group consisting of halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, —OR.sub.4 or —(CO)OR.sub.4; X.sub.4 each independently represents —COOR.sub.5; R.sub.3 each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl or C3-C6 cycloalkyl C1-C3 alkyl; R.sub.4 each independently represents hydrogen, C1-C6 alkyl or halogenated C1-C6 alkyl; R.sub.5 each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C6 cycloalkyl; preferably, Y represents chlorine; Z represents fluorine; R.sub.7 represents C1-C6 alkyl; R.sub.8 represents hydrogen; X.sub.3 represents halogen, formyl, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, —OR.sub.3, -(C1-C3 alkyl)-OR.sub.3, -(C1-C3 alkyl)-O(CO)R.sub.3, -(C1-C3 alkyl)-(CO)OR.sub.3, -(C1-C3 alkyl-O—(C1-C3 alkyl)-(CO)OR.sub.3, -(C1-C3 alkyl)-O(CO)(CO)OR.sub.3, phenyl or benzyl; wherein, the “C1-C6 alkyl” is each independently unsubstituted or substituted with one, two or three substituents selected from the group consisting of halogen; R.sub.3 each independently represents hydrogen or C1-C6 alkyl; R.sub.5 each independently represents hydrogen or C1-C6 alkyl; more preferably, Q represent ##STR00751##

5. A substituted-isoxazoline-containing aromatic compound with S configuration, as shown in general formula I′: ##STR00752## wherein, X.sub.3′ represents hydrogen, methyl or X.sub.3, the substituents X.sub.1, X.sub.2, X.sub.3, X.sub.4, Q, Y and Z are defined as shown in claims 1 to 4, and X.sub.3 and X.sub.4 are different; based on the content of stereoisomers having R and S configurations at this position, it has a stereochemical purity of 60-100% (S), preferably 70-100% (S), more preferably 80-100% (S), still more preferably 90-100% (S), still more preferably 95-100% (S).

6. The compound according to claim 1, which is selected from any one of the following compounds or the S configuration thereof: TABLE-US-00008 NO. Y Z Q 3 Cl F 4 Cl F 5 Cl F 6 Cl F 17 Cl F 26 Cl F 31 Cl F 33 Cl F 34 Cl F 35 Cl F 43 Cl F 52 Cl F 53 Cl F 54 Cl F 55 Cl F 56 Cl F 59 Cl F 105 Cl F 119 Cl F 126 Cl F 129 Cl F 132 Cl F 134 Cl F 135 Cl F 136 Cl F 142 Cl F 152 Cl F 203 Cl F 204 Cl F 205 Cl F 206 Cl F 218 Cl F 219 Cl F 220 Cl F 226 Cl F 228 Cl F 229 Cl F 230 Cl F 231 Cl F 232 Cl F alternatively it is selected from any one of the following compounds: TABLE-US-00009 NO. Y Z Q 1-2 Cl F 1-9 Cl F 1-37 Cl F 1-39 Cl F 1-55 Cl F 1-59 Cl F 1-60 Cl F 1-61 Cl Cl 1-62 Cl F 1-63 Cl F 1-64 Cl F 1-65 Cl F 1-66 Cl F 1-67 CF.sub.3 F 1-68 Br F 1-69 CN F 1-70 Cl F 1-71 Cl F 1-72 Cl F 1-73 Cl F 1-74 Cl F 1-75 Cl F 1-76 Cl F 1-79 Cl F 1-80 Cl F 1-81 Cl F 1-82 Cl F 1-83 Cl F 1-84 Cl F 1-86 Cl F 1-87 Cl F 1-88 Cl F 1-89 Cl F 1-90 Cl F 1-92 Cl F 1-94 Cl F 1-96 Cl F 1-98 Cl F 1-99 Cl F 1-100 Cl F 1-101 Cl F

7. A method for preparing the substituted-isoxazoline-containing aromatic compound according to claim 1, which is characterized by comprising the following steps: when Q represent ##STR00919## (1) subjecting a compound as shown in general formula II-1 and a compound as shown in general formula III-1 to cyclization reaction to obtain a compound as shown in general formula I-1, with the chemical reaction equation shown as follows: ##STR00920## when Q represent ##STR00921## (2) subjecting a compound as shown in general formula II-2 and a compound as shown in general formula III-2 to cyclization reaction to obtain a compound as shown in general formula I-2, with the chemical reaction equation shown as follows: ##STR00922## (3) subjecting a compound as shown in general formula II-3 and a compound as shown in general formula III-3 to reaction to obtain a compound as shown in general formula I-3; ##STR00923## (4) subjecting a compound as shown in general formula II-4 and a compound as shown in general formula III-4 to reaction to obtain a compound as shown in general formula I-4; ##STR00924## or, (5) subjecting a compound as shown in general formula I-5 and R.sub.6′-Hal to substitution reaction to obtain a compound as shown in general formula I-6, with the chemical reaction equation shown as follows: ##STR00925## wherein, L.sub.1, L.sub.2, L.sub.3, L.sub.4, L.sub.5, L.sub.6 and L.sub.7 each independently represent C1-C6 alkyl or aryl, preferably methyl, ethyl or phenyl; Hal represents halogen, preferably iodine; R.sub.6′ represents groups in R.sub.6 other than hydrogen; other substituents R.sub.1, R.sub.2, R.sub.6, R.sub.7, R.sub.8, X.sub.1, X.sub.2, X.sub.3, X.sub.4, Q.sub.1, Q.sub.2, Q.sub.3, Q.sub.4, Q.sub.5, Y and Z are defined as shown in claims 1-6; preferably, the steps (1), (2), (4) and (5) are all carried out in the presence of a base and a solvent; more preferably, the base is at least one selected from inorganic bases or organic bases; more preferably, the solvent is at least one selected from a group consisting of DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, dioxane, dichloromethane or ethyl acetate; preferably, the step (3) is carried out in the presence of an acid; more preferably, the acid is selected from acetic acid, hydrochloric acid or sulfuric acid.

8. An herbicidal composition, which is characterized in that it comprises at least one of the substituted-isoxazoline-containing aromatic compound according to claim 1 in a herbicidally effective amount, preferably, further comprises a formulation auxiliary.

9. A method of controlling a weed, which is characterized in that it comprises applying at least one of the substituted-isoxazoline-containing aromatic compound according to claim 1 or a herbicidal composition in a herbicidally effective amount on a plant or a weed area, wherein the herbicidal composition comprises at least one of the substituted-isoxazoline-containing aromatic compound according to claim 1 in a herbicidally effective amount.

10. (canceled)

11. The method of claim 9, wherein the herbicidal composition further comprises a formulation auxiliary.

12. The method of claim 9, wherein the weed is a weed in a useful crop, and the useful crop is a transgenic crop or a crop treated by genome editing technique.

Description

SPECIFIC MODE FOR CARRYING OUT THE INVENTION

[0122] The following embodiments are used to illustrate the present invention in detail and should not be taken as any limit to the present invention. The scope of the invention would be explained through the Claims.

[0123] In view of economics and variety of a compound, we preferably synthesized several compounds, part of which are listed in the following Table 1. The structure and information of a certain compound are shown in Table 1. The compounds in Table 1 are listed for further explication of the present invention, other than any limit therefor. The subject of the present invention should not be interpreted by those skilled in the art as being limited to the following compounds.

TABLE-US-00001 TABLE 1 Structures and .sup.1H NMR data of compounds [00025] NO. [00026] Y Z Q .sup.1H NMR 1 [00027] Cl F [00028] 2 [00029] Cl F [00030] 3 [00031] Cl F [00032] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.99- 7.90 (m, 2H), 4.22 (q, J = 7.0 Hz, 2H), 3.86 (d, J = 17.5 Hz, 1H), 3.65 (s, 6H), 3.56 (d, J = 17.5 Hz, 1H), 2.07-1.89 (m, 2H), 1.25 (t, J = 7.0 Hz, 3H), 0.92 (t, J = 7.5 Hz, 3H). 4 [00033] Cl F [00034] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.95-7.90(m, 2H), 4.21 (q, J = 7.0 Hz, 2H), 3.86 (d, J = 18.0 Hz, 1H), 3.65 (s, 6H), 3.57 (d, J = 18.0 Hz, 1H), 1.94 (t, J = 8.0 Hz, 2H), 1.40-1.28 (m, 2H), 1.24 (t, J = 7.0 Hz, 3H), 0.93 (t, J = 7.5 Hz, 3H) 5 [00035] Cl F [00036] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.92-7.90 (m, 2H), 4.32-4.16 (m, 2H), 3.80 (d, J = 18.0 Hz, 1H), 3.55 (d, J = 18.0 Hz, 1H), 2.35-2.25 (m, 1H), 1.24-1.22 (m, 3H), 1.25-0.90 (m, 6H). 6 [00037] Cl F [00038] .sup.1H NMR (500 MHz, CDCl.sub.3) δ 7.76 (d, J = 7.5 Hz, 1H), 7.40 (d, J = 9.0 Hz, 1H), 4.41-4.26 (m, 2H), 3.98 (d, J = 17.5 Hz, 1H), 3.81 (s, 6H), 3.47 (d, J = 17.5 Hz, 1H), 2.08-2.01 (m, 2H), 1.45-1.40 (m, 2H), 1.40-1.34 (m, 2H), 0.96 (t, J = 6.5 Hz, 3H), 0.93 (d, J = 6.5 Hz, 3H). 7 [00039] Cl F [00040] 8 [00041] Cl F [00042] 9 [00043] Cl F [00044] 10 [00045] Cl F [00046] 11 [00047] Cl F [00048] 12 [00049] Cl F [00050] 13 [00051] Cl F [00052] 14 [00053] Cl F [00054] 15 [00055] Cl F [00056] 16 [00057] Cl F [00058] 17 [00059] Cl F [00060] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.94-7.91 (m, 2H), 4.23 (q, J = 7.5 Hz, 2H), 3.88 (d, J = 18.0 Hz, 1H), 3.65 (s, 6H), 3.46 (d, J = 18.0 Hz, 1H), 1.48- 1.46 (m, 1H), 1.26 (1, J = 7.5 Hz, 3H), 0.60-0.50 (m, 3H), 0.37-0.34 (m, 1H). 18 [00061] Cl F [00062] 19 [00063] Cl F [00064] 20 [00065] Cl F [00066] 21 [00067] Cl F [00068] 22 [00069] Cl F [00070] 23 [00071] Cl F [00072] 24 [00073] Cl F [00074] 25 [00075] Cl F [00076] 26 [00077] Cl F [00078] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.94 (d, J = 7.5 Hz, 1H), 7.90 (d, J = 9.5 Hz, 1H), 4.23-4.17 (m, 2H), 3.88 (d, J = 17.5 Hz, 1H), 3.67-3.62 (m, 7H), 1.90 (d, J = 7.0 Hz, 2H), 1.24 (t, J = 7.0 Hz, 3H), 0.76- 0.68 (m, 1H), 0.45-0.41 (m, 2H), 0.16- 0.12 (m, 2H). 27 [00079] Cl F [00080] 28 [00081] Cl F [00082] 29 [00083] Cl F [00084] 30 [00085] Cl F [00086] 31 [00087] Cl F [00088] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.00 (d, J = 8.0 Hz, 1H), 7.94 (d, J = 9.5 Hz, 1H), 4.26 (q, J = 7.0 Hz, 2H), 4.08-4.01 (m, 2H), 3.99 (d, J = 17.5 Hz, 1H), 3.68-3.62 (m, 7H), 1.29-1.25 (m, 3H). 32 [00089] Cl F [00090] 33 [00091] Cl F [00092] 1H NMR (500 MHz, DMSO-d.sub.6) δ 8.02 (d, J = 7.5 Hz, 1H), 7.98 (d, J = 9.5 Hz, 1H), 4.37-4.31 (m, 3H), 4.18 (d, J = 18.5 Hz, 1H), 3.65 (s, 6H), 1.28 (1, J = 7.5 Hz, 3H). 34 [00093] Cl F [00094] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.94 (d, J = 7.5 Hz, 1H), 7.91 (d, J = 9.5 Hz, 1H), 4.65 (t, J = 5.5 Hz, 1H), 4.56 (t, J = 5.5 Hz, 1H), 4.19 (q, J = 7.0 Hz, 2H), 3.90 (d, J = 17.5 Hz, 1H), 3.69 (d, J = 17.5 Hz, 1H), 3.62 (s, 6H), 2.45-2.37 (m, 2H), 1.22 (t, J = 7.0 Hz, 3H). 35 [00095] Cl F [00096] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.97 (d, J = 7.5 Hz, 1H), 7.93 (d, J = 9.5 Hz, 1H), 6.38-6.16 (m, 1H), 4.25-4.20 (m, 2H), 3.95 (d, J = 17.5 Hz, 1H), 3.77 (d, J = 17.5 Hz, 1H), 3.65 (s, 6H), 2.75-2.68 (m, 2H), 1.26-1.23 (m, 3H) 36 [00097] Cl F [00098] 37 [00099] Cl F [00100] 38 [00101] Cl F [00102] 39 [00103] Cl F [00104] 40 [00105] Cl F [00106] 41 [00107] Cl F [00108] 42 [00109] Cl F [00110] 43 [00111] Cl F [00112] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.97-7.91 (m, 2H), 4.22 (q, J = 7.0 Hz, 2H), 3.90-3.75 (m, 3H), 3.67-3.64 (m, 7H), 3.56-3.53 (m, 2H), 1.24 (t, J = 7.0 Hz, 3H), 1.11 (t, J = 7.0 Hz. 3H). 44 [00113] Cl F [00114] 45 [00115] Cl F [00116] 46 [00117] Cl F [00118] 47 [00119] Cl F [00120] 48 [00121] Cl F [00122] 49 [00123] Cl F [00124] 50 [00125] Cl F [00126] 51 [00127] Cl F [00128] 52 [00129] Cl F [00130] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.74 (d, J = 7.5 Hz, 1H), 7.40 (d, J = 9.0 Hz, 1H), 4.12-4.06 (m, 1H), 3.76 (s, 6H), 3.71- 3.65 (m, 1H), 3.30-3.12 (m, 2H). 53 [00131] Cl F [00132] .sup.1H NMR (500 MHz, Chloroform-d) δ 7.75 (d, J = 7.5 Hz, 1H), 7.41 (d, J = 9.0 Hz, 1H), 4.36-4.28 (m, 2H), 4.23-4.15 (m, 3H), 3.81 (s, 6H), 3.69 (d, J = 17.5 Hz, 1H), 3.27 (d, J = 17.5 Hz, 1H), 3.07-2.96 (m, 1H), 1.35 (t, J = 7.0 Hz, 3H), 1.30 (t, J = 7.0 Hz, 3H). 54 [00133] Cl F [00134] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.99-7.91 (m, 2H), 4.26-4.20 (m, 4H), 4.15 (q, J = 7.5Hz, 2H), 3.96-3.93 (m, 2H), 3.89-3.76 (m, 2H), 3.65 (s, 6H), 1.25 (t, J = 7.5 Hz, 3H), 1.21 (t, J = 7.5 Hz, 3H). 55 [00135] Cl F [00136] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.97 (d, J = 7.5 Hz, 1H), 7.92 (d, J = 9.5 Hz, 1H), 4.30-4.09 (m, 4H), 3.98-3.92 (m, 1H), 3.88-3.78 (m, 3H), 3.77-3.72 (m, 1H), 3.65 (s, 6H), 1.30-1.28 (m, 3H), 1.26- 1.23 (m, 3H), 1.22-1.18 (m, 3H). 56 [00137] Cl F [00138] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.01- 7.90 (m, 2H), 7.55-7.39 (m, 5H), 4.43 (d, J = 17.5 Hz, 1H), 3.91 (d, J = 17.5 Hz, 1H), 3.74 (s, 3H), 3.64 (s, 6H). 57 [00139] Cl F [00140] 58 [00141] Cl F [00142] 59 [00143] Cl F [00144] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.86-7.81 (m, 2H), 7.35-7.22 (m, 5H), 3.82 (d, J = 17.5 Hz, 1H), 3.71 (s, 3H), 3.62-3.59 (m, 7H), 3.34-3.24 (m, 2H). 60 [00145] Cl F [00146] 61 [00147] Cl F [00148] 62 [00149] Cl F [00150] 63 [00151] Cl F [00152] 64 [00153] Cl F [00154] 65 [00155] Cl F [00156] 66 [00157] Cl F [00158] 67 [00159] Cl F [00160] 68 [00161] Cl F [00162] 69 [00163] Cl F [00164] 70 [00165] Cl F [00166] 71 [00167] Cl F [00168] 72 [00169] Cl F [00170] 73 [00171] Cl F [00172] 74 [00173] Cl F [00174] 75 [00175] Cl F [00176] 76 [00177] Cl F [00178] 77 [00179] Cl F [00180] 78 [00181] Cl F [00182] 79 [00183] Cl F [00184] 80 [00185] Cl F [00186] 81 [00187] Cl F [00188] 82 [00189] Cl F [00190] 83 [00191] Cl F [00192] 84 [00193] Cl F [00194] 85 [00195] Cl F [00196] 86 [00197] Cl F [00198] 87 [00199] Cl F [00200] 88 [00201] Cl F [00202] 89 [00203] Cl F [00204] 90 [00205] Cl F [00206] 91 [00207] Cl F [00208] 92 [00209] Cl F [00210] 93 [00211] Cl F [00212] 94 [00213] Cl F [00214] 95 [00215] Br F [00216] 96 [00217] CF.sub.3 F [00218] 97 [00219] CN F [00220] 98 [00221] Br F [00222] 99 [00223] CF.sub.3 F [00224] 100 [00225] CN F [00226] 101 [00227] Cl F [00228] 102 [00229] Cl F [00230] 103 [00231] Cl F [00232] 104 [00233] Cl F [00234] 105 [00235] Cl F [00236] 1H NMR (500 MHz, DMSO-d.sub.6) δ 7.92- 7.87 (m, 2H), 6.64 (s, 1H), 4.21 (q, J = 7.0 Hz, 2H), 3.86 (dd, J = 18.0, 5.5 Hz, 1H), 3.56 (dd, J = 18.0, 5.5 Hz, 1H), 3.43 (s, 3H), 1.99-1.95 (m, 2H), 1.24 (t, J = 7.0 Hz, 3H), 0.92 (t, J = 7.0 Hz, 3H). 106 [00237] Cl F [00238] 107 [00239] Cl F [00240] 108 [00241] Cl F [00242] 109 [00243] Cl F [00244] 110 [00245] Cl F [00246] 111 [00247] Cl F [00248] 112 [00249] Cl F [00250] 113 [00251] Cl F [00252] 114 [00253] Cl F [00254] 115 [00255] Cl F [00256] 116 [00257] Cl F [00258] 117 [00259] Cl F [00260] 118 [00261] Cl F [00262] 119 [00263] Cl F [00264] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.91-7.86 (m, 2H), 6.64 (s, 1H), 4.23 (q, J = 7.0 Hz, 2H), 3.88 (dd, J = 17.5, 5.5 Hz, 1H), 3.48 (dd, J = 17.5, 5.5 Hz, 1H), 3.44 (s, 3H), 1.54-1.41 (m, 1H), 1.26 (t, J = 7.0 Hz, 3H), 0.57-0.52 (m, 3H), 0.37- 0.34 (m, 1H). 120 [00265] Cl F [00266] 121 [00267] Cl F [00268] 122 [00269] Cl F [00270] 123 [00271] Cl F [00272] 124 [00273] Cl F [00274] 125 [00275] Cl F [00276] 126 [00277] Cl F [00278] .sup.1H NMR (500 MHz, DMSO) δ 7.88-7.86 (m, 2H), 6.60 (s, 1H), 4.45-4.40(m, 1H), 4.36-4.33 (m, 1H), 4.23-4.11 (m, 2H), 3.39 (s, 3H), 2.12-2.02 (m, 1H), 1.73-1.62 (m, 3H), 1.54-1.46 (m, 3H), 1.20-1.18 (m, 3H). 127 [00279] Cl F [00280] 128 [00281] Cl F [00282] 129 [00283] Cl F [00284] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.02-7.79 (m, 2H), 6.65 (s, 1H), 4.45 (m, 1H), 4.18-4.02 (m, 1H), 3.89 (s, 3H), 3.44 (s, 3H). 130 [00285] Cl F [00286] 131 [00287] Cl F [00288] 132 [00289] Cl F [00290] 1H NMR (500 MHz, DMSO-d.sub.6) δ 7.93- 7.88 (m, 2H), 6.63 (s, 1H), 4.92-4.74 (m, 2H), 4.25 (q, J = 7.0 Hz, 2H), 3.93-3.88 (m 1H), 3.77-3.70 (m, 1H), 3.44 (s, 3H), 1.25 (t, J = 7.0 Hz, 3H). 133 [00291] Cl F [00292] 134 [00293] Cl F [00294] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.93-7.91 (m, 2H), 6.72-6.45 (m, 2H), 4.28 (t, J = 7.0 Hz, 2H), 4.12-3.84 (m, 2H), 3.42 (s, 3H), 1.25 (t, J = 7.0 Hz, 3H). 135 [00295] Cl F [00296] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.99- 7.93 (m, 2H), 6.65 (s, 1H), 4.37-4.32 (m, 3H), 4.23-4.17 (m, 1H), 3.44 (s, 3H), 1.27 (t, J = 7.0 Hz, 3H). 136 [00297] Cl F [00298] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.90 (dd, J = 10.5, 8.5 Hz, 2H), 6.63 (s, 1H), 4.71-4.56 (m. 2H), 4.21 (q, J = 7.0 Hz, 2H), 3.97-3.88 (m, 1H), 3.70-3.68 (m, 1H), 3.44 (s, 3H), 2.43-2.40 (m, 2H), 1.24 (t, J = 7.0, 3H). 137 [00299] Cl F [00300] 138 [00301] Cl F [00302] 139 [00303] Cl F [00304] 140 [00305] Cl F [00306] 141 [00307] Cl F [00308] 142 [00309] Cl F [00310] .sup.1H NMR (500 MHz, DMSO) δ 7.90-7.79 (m, 2H), 6.59 (s, 1H), 5.47 (t, J = 6.0 Hz, 1H), 4.16 (q, J = 7.0 Hz, 2H), 3.79-3.66 (m, 3H), 3.63-3.61 (m, 1H), 3.39 (s, 3H), 1.20-1.18 (m, 3H). 143 [00311] Cl F [00312] 144 [00313] Cl F [00314] 145 [00315] Cl F [00316] 146 [00317] Cl F [00318] 147 [00319] Cl F [00320] 148 [00321] Cl F [00322] 149 [00323] Cl F [00324] 150 [00325] Cl F [00326] 151 [00327] Cl F [00328] 152 [00329] Cl F [00330] 1H NMR (500 MHz, DMSO-d6) δ 10.23 (s, 1H), 7.94-7.89 (m, 2H), 6.64 (s, 1H), 4.29-4.27 (m, 2H), 4.21-4.18 (m, 2H), 3.43 (s, 3H), 1.26-1.23 (m, 3H). 153 [00331] Cl F [00332] 154 [00333] Cl F [00334] 155 [00335] Cl F [00336] 156 [00337] Cl F [00338] 157 [00339] Cl F [00340] 158 [00341] Cl F [00342] 159 [00343] Cl F [00344] 160 [00345] Cl F [00346] 161 [00347] Cl F [00348] 162 [00349] Cl F [00350] 163 [00351] Cl F [00352] 164 [00353] Cl F [00354] 165 [00355] Cl F [00356] 166 [00357] Cl F [00358] 167 [00359] Cl F [00360] 168 [00361] Cl F [00362] 169 [00363] Cl F [00364] 170 [00365] Cl F [00366] 171 [00367] Cl F [00368] 172 [00369] Cl F [00370] 173 [00371] Cl F [00372] 174 [00373] Cl F [00374] 175 [00375] Cl F [00376] 176 [00377] Cl F [00378] 177 [00379] Cl F [00380] 178 [00381] Cl F [00382] 179 [00383] Cl F [00384] 180 [00385] Cl F [00386] 181 [00387] Cl F [00388] 182 [00389] Cl F [00390] 183 [00391] Cl F [00392] 184 [00393] Cl F [00394] 185 [00395] Cl F [00396] 186 [00397] Cl F [00398] 187 [00399] Cl F [00400] 188 [00401] Cl F [00402] 189 [00403] Cl F [00404] 190 [00405] Cl F [00406] 191 [00407] Cl F [00408] 192 [00409] Cl F [00410] 193 [00411] Cl F [00412] 194 [00413] Cl F [00414] 195 [00415] Cl F [00416] 196 [00417] Cl F [00418] 197 [00419] Br F [00420] 198 [00421] CF.sub.3 F [00422] 199 [00423] CN F [00424] 200 [00425] Br F [00426] 201 [00427] CF.sub.3 F [00428] 202 [00429] CN F [00430] 203 [00431] Cl F [00432] 1H NMR (500 MHz, Chloroform-d) δ 7.72 (d, J = 7.5 Hz, 1H), 7.38 (d, J = 9.0 Hz, 1H), 4.36-4.23 (m, 5H), 4.03-3.94 (m, 1H), 3.80 (s, 3H), 3.52-3.43 (m, 1H), 2.13-2.04 (m, 2H), 1.37 (t, J = 7.0 Hz, 3H), 1.05 (t, J = 7.5 Hz, 3H). 204 [00433] Cl F [00434] 1H NMR (500 MHz, DMSO) δ 7.93 (d, J = 7.5 Hz, 1H), 7.90 (d, J = 9.5 Hz, 1H), 4.29-4.21 (m, 2H), 4.15 (s, 3H), 3.82-3.80 (m, 1H), 3.63 (s, 3H), 3.57-3.55 (m, 1H), 2.34-2.30 (m, 1H), 1.22 (t, J = 7.5 Hz, 3H), 0.94-0.92 (m, 6H). 205 [00435] Cl F [00436] 1H NMR (500 MHz, DMSO) δ 7.94 (d, J = 8.0 Hz, 1H), 7.89 (d, J = 9.5 Hz, 1H), 4.21 (q, J = 7.0 Hz, 2H), 4.15 (s, 3H), 3.88-3.82 (m, 1H), 3.63 (s, 3H), 3.58-3.52 (m, 1H), 1.99-1.91 (m, 2H), 1.39-1.27 (m, 4H), 1.24 (t, J = 7.0 Hz, 3H), 0.89 (t, J = 6.5 Hz, 3H). 206 [00437] Cl F [00438] 1H NMR (500 MHz, DMSO-d6) δ 8.02 (d, J = 7.5 Hz, 1H), 7.96 (d, J = 9.5 Hz, 1H), 4.38-4.29 (m, 3H), 4.17-4.13 (m, 4H), 3.63 (s, 3H), 1.28 (t, J = 7.0 Hz, 3H). 207 [00439] Cl F [00440] 208 [00441] Cl F [00442] 209 [00443] Cl F [00444] 210 [00445] Cl F [00446] 211 [00447] Cl F [00448] 212 [00449] Cl F [00450] 213 [00451] Cl F [00452] 214 [00453] Cl F [00454] 215 [00455] Cl F [00456] 216 [00457] Cl F [00458] 217 [00459] Cl F [00460] 218 [00461] Cl F [00462] 1H NMR (500 MHz, DMSO-d6) δ 10.23 (s, 1H), 7.94-7.89 (m, 2H), 6.64 (s, 1H), 4.65-4.23 (m, 2H), 4.29-4.27 (m, 2H), 4.21-4.18 (m, 2H), 3.43 (s, 3H), 1.26-1.23 (m, 3H). 219 [00463] Cl F [00464] 1H NMR (500 MHz, DMSO) δ 7.88-7.86 (m, 2H), 6.60 (s, 1H), 4.45-4.40 (m, 1H), 4.36-4.33 (m, 1H), 4.23-4.11 (m, 2H), 3.86-3.84 (m, 1H), 3.75-3.68 (m, 1H), 3.39 (s, 3H), 2.01 (s, 3H), 1.20-1.18 (m, 3H). 220 [00465] Cl F [00466] 1H NMR (500 MHz, DMSO-d6) δ 7.91- 7.86 (m, 2H), 6.61 (s, 1H), 4.68 (d, J = 12.0 Hz, 1H), 4.59 (d, J = 12.0 Hz, 1H), 4.25-4.08 (m, 4H), 3.42 (s, 3H), 1.25-1.20 (m, 3H). 221 [00467] Cl F [00468] 222 [00469] Cl F [00470] 223 [00471] Cl F [00472] 224 [00473] Cl F [00474] 225 [00475] Cl F [00476] 226 [00477] Cl F [00478] .sup.1H NMR (500 MHz, DMSO-d6) δ 7.94 (dd, J = 8.5, 5.5 Hz, 2H), 6.64 (s, 1H), 4.09 (m, 1H), 3.82 (s, 3H), 3.69 (m, 1H), 3.44 (s, 3H), 3.34 (s, 3H). 227 [00479] Cl F [00480] 228 [00481] Cl F [00482] .sup.1H NMR (500 MHz, DMSO-d6) δ 7.91- 7.88 (m, 2H), 7.12 (s, 1H), 4.21 (q, J = 7.0 Hz, 2H), 3.85 (dd, J = 18.0, 3.0 Hz, 1H), 3.55 (dd, J = 18.0, 3.0 Hz, 1H), 3.43 (s, 3H), 2.00-1.97 (m, 2H), 1.24 (t, J = 7.0 Hz, 3H), 0.92 (t, J = 7.5 Hz, 3H). 229 [00483] Cl F [00484] .sup.1H NMR (500 MHz, DMSO-d6) δ 8.16 (d, J = 8.0 Hz, 1H), 8.06 (d, J = 9.0 Hz, 1H), 6.98 (s, 1H), 4.22 (t, J = 7.0 Hz, 2H), 3.89- 3.83 (m 1H), 3.58-3.53 (m, 1H), 3.42 (s, 3H), 2.00-1.94 (m, 2H), 1.25 (t, J = 7.0 Hz, 3H), 0.92 (t, J = 7.5 Hz, 3H). 230 [00485] Cl F [00486] .sup.1H NMR (500 MHz, DMSO-d6) δ 8.17 (d, J = 7.5 Hz, 1H), 8.08 (d, J = 9.5 Hz, 1H), 7.65 (s, 1H), 4.22 (q, J = 7.0 Hz, 2H), 3.86 (dd, J = 18.0, 7.5 Hz, 1H), 3.55 (dd, J = 18.0, 7.5 Hz, 1H), 3.42 (s, 3H),1.98 (q, J = 7.0 Hz, 2H), 1.25 (t, J = 7.0 Hz, 3H), 0.92 (t, J = 7.0 Hz, 3H). 231 [00487] Cl F [00488] .sup.1H NMR (500 MHz, DMSO-d6) δ 7.92-7.87 (m, 2H), 7.12 (s, 1H), 4.23 (q, J = 7.0 Hz, 2H), 3.88 (dd, J = 17.5, 5.5 Hz, 1H), 3.48-3.45 (m 1H), 3.43 (s, 3H), 1.49-1.46 (m, 1H), 1.25 (t, J = 7.0 Hz, 3H), 0.57-0.52 (m, 3H), 0.37-0.34 (m, 1H). 232 [00489] Cl F [00490] .sup.1H NMR (500 MHz, DMSO-d6) δ 9.14 (d, J = 9.5 Hz, 1H), 8.53 (d, J = 7.5 Hz, 1H), 7.10 (s, 1H), 4.42-4.40 (m, 1H), 4.35 (t, J = 7.0 Hz, 2H), 4.25-4.23 (m, 1H), 2.52 (s, 3H), 1.31 (t, J = 7.0 Hz, 3H). 233 [00491] Cl F [00492] 234 [00493] Cl F [00494] 235 [00495] Cl F [00496] 236 [00497] Cl F [00498]

[0124] Table A is constructed in the same way as that of Table 1 above, except for replacing the racemate compounds having a chiral center (the carbon atom (C *) connected to X.sub.3 and X.sub.4 in general formula I

##STR00499##

is a chiral center, that is, X.sub.3, X.sub.4 are not the same) (that is, compounds 1-50, 52-90, 92-93, 95-152, 154-192, 194-195 and 197-236) with the corresponding compounds in S configuration and deleting the compounds having no chiral center at the corresponding position, and in Table A, the entries in the column “NO.” are listed in sequence as “1(S)-50(S), 52(S)-90(S), 92(S)-93(S), 95(S)-152(S), 154(S)-192(S), 194(S)-195(S) and 197(S)-236(S)”. For example, “1(S)” corresponds to S configuration of compound “1” in Table 1, “119(S)” corresponds to S configuration of compound “119” in Table 1.

TABLE-US-00002 TABLE B Structures and .sup.1H NMR date of compounds [00500] NO. [00501] Y Z Q .sup.1H NMR 1-1  [00502] Cl F [00503] 1-2  [00504] Cl F [00505] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.90-7.88 (m, 2H), 6.63 (s, 1H), 5.36 (dd, J = 12.0, 6.0 Hz, 1H), 4.20 (q, J = 7.0 Hz, 2H), 3.90-3.84 (m, 1H), 3.72-3.66 (m, 1H), 3.44 (s, 3H), 1.25 (t, J = 7.0 Hz, 3H). 1-3  [00506] Cl F [00507] 1-4  [00508] Cl F [00509] 1-5  [00510] Cl F [00511] 1-6  [00512] Cl F [00513] 1-7  [00514] Cl F [00515] 1-8  [00516] Cl Cl [00517] 1-9  [00518] Cl F [00519] .sup.1H NMR (500 MHz, Chloroform-d) δ 7.72 (d, J = 7.5 Hz, 1H), 7.39 (d, J = 9.0 Hz, 1H), 6.41 (s, 1H), 4.39-4.25 (m, 2H), 4.04-3.95 (m, 1H), 3.60 (s, 3H), 3.51- 3.31 (m, 1H), 1.75 (d, J = 2.5 Hz, 3H), 1.36 (td, J = 7.1, 1.7 Hz, 3H). 1-10  [00520] CF.sub.3 F [00521] 1-11  [00522] Br F [00523] 1-12  [00524] CN F [00525] 1-13  [00526] Cl F [00527] 1-14  [00528] Cl F [00529] 1-15  [00530] Cl F [00531] 1-16  [00532] Cl F [00533] 1-17  [00534] Cl F [00535] 1-18  [00536] Cl F [00537] 1-19  [00538] Cl F [00539] 1-20  [00540] Cl F [00541] 1-21  [00542] Cl F [00543] 1-22  [00544] Cl F [00545] 1-23  [00546] Cl F [00547] 1-24  [00548] Cl F [00549] 1-25  [00550] Cl F [00551] 1-26  [00552] Cl F [00553] 1-27  [00554] Cl F [00555] 1-28  [00556] Cl F [00557] 1-29  [00558] Cl F [00559] 1-30  [00560] Cl F [00561] 1-31  [00562] Cl F [00563] 1-32  [00564] Cl F [00565] 1-33 [00566] Cl F [00567] 1-34  [00568] Cl F [00569] 1-35  [00570] Cl F [00571] 1-36  [00572] Cl F [00573] 1-37  [00574] Cl F [00575] .sup.1H NMR (500 MHz, DMSO) δ 7.87 (d, J = 9.5 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 6.63 (s, 1H), 4.10-4.03 (m, 2H), 3.44 (s, 3H), 3.44-3.37 (m, 1H), 3.28-3.22 (m, 1H), 2.44-2.40 (m, 2H), 2.03-1.92 (m, 2H), 1.40 (s, 3H), 1.19 (t, J = 7.0 Hz, 3H). 1-38  [00576] Cl F [00577] 1-39  [00578] Cl F [00579] .sup.1H NMR (500 MHz, DMSO) δ 7.86-7.85 (m, 2H), 6.63 (s, 1H), 4.07 (q, J = 7.0 Hz, 2H), 3.44 (s, 3H), 3.33 (d, J = 17.0 Hz, 1H), 3.22 (d, J = 17.0 Hz, 1H), 2.35-2.34 (m, 2H), 1.73-1.58 (m, 4H), 1.38 (s, 3H), 1.19 (t, J = 7.0 Hz, 3H). 1-40  [00580] Cl F [00581] 1-41  [00582] Cl F [00583] 1-42  [00584] Cl F [00585] 1-43  [00586] Cl F [00587] 1-44  [00588] Cl F [00589] 1-45  [00590] Cl F [00591] 1-46  [00592] Cl F [00593] 1-47  [00594] Cl F [00595] 1-48  [00596] Cl F [00597] 1-49  [00598] Cl F [00599] 1-50  [00600] Cl F [00601] 1-51  [00602] Cl F [00603] 1-52  [00604] Cl F [00605] 1-53  [00606] Cl F [00607] 1-54  [00608] Cl F [00609] 1-55  [00610] Cl F [00611] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.97 (d, J = 7.5 Hz, 1H), 7.92 (d, J = 9.5 Hz, 1H), 5.38-5.34 (m, 1H), 4.20 (q, J = 7.0 Hz, 2H), 3.90-3.85 (m, 1H), 3.73-3.67 (m, 1H), 3.65 (s, 6H), 1.25 (t, J = 7.0 Hz, 3H). 1-56  [00612] Cl F [00613] 1-57  [00614] Cl F [00615] 1-58  [00616] Cl F [00617] 1-59  [00618] Cl F [00619] .sup.1H NMR (500 MHz, DMSO) δ 13.39 (s, 1H), 7.96 (d, J = 7.5 Hz, 1H), 7.90 (d, J = 9.5 Hz, 1H), 3.90 (d, J = 17.0 Hz, 1H), 3.65 (s, 6H), 3.49 (d, J = 17.0 Hz, 1H), 1.62 (s, 3H). 1-60  [00620] Cl F [00621] .sup.1H NMR (500 MHz, DMSO) δ 7.97 (d, J = 7.5 Hz, 1H), 7.91 (d, J = 9.5 Hz, 1H), 3.93 (d, J = 17.5 Hz, 1H), 3.75 (s, 3H), 3.65 (s, 6H), 3.53 (t, J = 17.5 Hz, 1H), 1.64 (s, 3H). 1-61  [00622] Cl Cl [00623] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.09 (s, 1H), 8.02 (s, 1H), 4.22 (q, J = 7.0 Hz, 2H), 3.94 (d, J = 17.5 Hz, 1H), 3.66 (s, 6H), 3.56 (d, J = 17.5 Hz, 1H), 1.64 (s, 3H), 1.24 (t, J = 7.0 Hz, 3H). 1-62  [00624] Cl F [00625] .sup.1H NMR (500 MHz, DMSO-d6) δ 7.94 (d, J = 7.5 Hz, 1H), 7.90 (d, J = 9.5 Hz, 1H), 4.19 (q, J = 7.0 Hz, 2H), 3.89 (d, J = 17.5 Hz, 1H), 3.63 (s, 6H), 3.52 (d, J = 17.5 Hz, 1H), 1.62 (s, 3H), 1.23 (t, J = 7.0 Hz, 3H). 1-63  [00626] Cl F [00627] .sup.1H NMR (500 MHz, DMSO) δ 7.95 (d, J = 7.5 Hz, 1H), 7.93 (d, J = 9.5 Hz, 1H), 4.20 (q, J = 7.0 Hz, 2H), 3.91 (d, J = 17.5 Hz, 1H), 3.53 (d, J = 17.5 Hz, 1H), 3.25 (s, 6H), 1.63 (s, 3H), 1.25 (t, J = 7.0 Hz, 3H). 1-64  [00628] Cl F [00629] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.00 (d, J = 7.5 Hz, 1H), 7.90 (d, J = 9.5 Hz, 1H), 4.40-4.32 (m, 4H), 4.19 (q, J = 7.0 Hz, 2H), 3.90 (d, J = 17.5 Hz, 1H), 3.53 (d, J = 17.5 Hz, 1H), 1.62 (s, 3H), 1.27-1.21 (m, 9H). 1-65  [00630] Cl F [00631] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.00 (d, J = 7.5 Hz, 1H), 7.90 (d, J = 9.5 Hz, 1H), 6.01-5.95 (m, 2H), 4.20 (q, J = 7.0 Hz, 2H), 3.92 (d, J = 17.5 Hz, 1H), 3.56 (d, J = 17.5 Hz, 1H), 1.64 (s, 3H), 1.46-1.42 (m, 12H), 1.24 (t, J = 7.0 Hz, 3H). 1-66  [00632] Cl F [00633] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.98 (d, J = 7.5 Hz 1H), 7.89 (d, J = 9.5 Hz, 1H), 4.21 (q, J = 7.0 Hz, 2H), 3.91 (d, J = 17.5 Hz, 1H), 3.54 (d, J = 17.5 Hz, 1H), 2.88-2.85 (m, 2H), 1.64 (s, 3H), 1.25 (t, J = 7.0 Hz, 3H), 1.19-1.04 (m, 4H), 0.92- 0.75 (m, 4H). 1-67  [00634] CF.sub.3 F [00635] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.16 (d, J = 9.5 Hz, 1H), 8.00 (d, J = 7.0 Hz, 1H), 4.21 (q, J = 7.0 Hz, 2H), 3.80 (d, J = 17.5 Hz, 1H), 3.66 (s, 6H), 3.41 (d, J = 17.5 Hz, 1H), 1.63 (s, 3H), 1.25 (t, J = 7.0 Hz, 3H). 1-68  [00636] Br F [00637] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.07 (d, J = 9.5 Hz, 1H), 7.86 (d, J = 7.5 Hz, 1H), 4.21 (q, J = 7.0 Hz, 2H), 3.91 (d, J = 17.5 Hz, 1H), 3.64 (s, 6H), 3.52 (d, J = 17.5 Hz, 1H), 1.64 (s, 3H), 1.25 (t, J = 7.0 Hz, 3H). 1-69  [00638] CN F [00639] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.33 (d, J = 9.5 Hz, 1H), 8.12 (d, J = 7.0 Hz, 1H), 4.21 (q, J = 7.0 Hz, 2H), 3.93 (d, J = 17.0 Hz, 1H), 3.65 (s, 6H), 3.54 (d, J = 17.0 Hz, 1H), 1.66 (s, 3H), 1.25 (t, J = 7.0 Hz, 3H). 1-70  [00640] Cl F [00641] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.94 (d, J = 7.5 Hz, 1H), 7.90 (d, J = 9.5 Hz, 1H), 4.10 (t, J = 6.5 Hz, 2H), 3.90 (d, J = 17.5 Hz, 1H), 3.63 (s, 6H), 3.52 (d, J = 17.5 Hz, 1H), 1.63 (s, 3H), 1.62-1.58 (m, 2H), 0.88 (q, J = 7.0 Hz, 3H). 1-71  [00642] Cl F [00643] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.94 (d, J = 7.5 Hz, 1H), 7.90 (d, J = 9.5 Hz, 1H), 4.99 (p, J = 6.0 Hz, 1H), 4.05 (d, J = 17.5 Hz, 1H), 3.64 (s, 6H), 3.52 (d, J = 17.5 Hz, 1H), 1.62 (s, 3H), 1.30 (d, J = 6.0 Hz, 1H). 1-72  [00644] Cl F [00645] .sup.1H NMR (500 MHz, DMSO) δ 7.94 (d, J = 7.5 Hz, 1H), 7.90 (d, J = 9.5 Hz, 1H), 4.14 (t, J = 6.0 Hz, 2H), 3.89 (d, J = 17.5 Hz, 1H), 3.63 (s, 6H), 3.52 (d, J = 17.5 Hz, 1H), 1.62 (s, 3H), 1.62-1.55 (m, 2H), 1.39- 1.28 (m, 2H), 0.89 (t, J = 7.0 Hz, 3H). 1-73  [00646] Cl F [00647] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.94 (d, J = 7.5 Hz, 1H), 7.90 (d, J = 9.5 Hz, 1H), 3.94 (d, J = 6.5 Hz, 2H), 3.91 (d, J = 17.5 Hz, 1H), 3.63 (s, 6H), 3.53 (d, J = 17.5 Hz, 1H), 1.97-1.88 (m, 1H), 1.64 (s, 3H), 0.90 (d, J = 6.5 Hz, 6H). 1-74  [00648] Cl F [00649] .sup.1H NMR (500 MHz, DMSO) δ 7.96-7.87 (m, 2H), 3.84 (d, J = 17.5 Hz, 1H), 3.63 (s, 6H), 3.46 (d, J = 17.5 Hz, 1H), 1.57 (s, 3H), 1.44 (s, 9H). 1-75  [00650] Cl F [00651] .sup.1H NMR (500 MHz, DMSO) δ 7.96-7.93 (m, 2H), 4.90-4.87 (m, 1H), 3.88 (d, J = 17.5, 1H), 3.64 (s, 6H), 3.53 (d, J = 17.5 Hz, 1H), 1.63 (s, 3H), 1.26-1.21 (m, 10H), 0.85 (t, J = 7.5 Hz, 3H). 1-76  [00652] Cl F [00653] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.97 (d, J = 7.5 Hz, 1H), 7.92 (d, J = 9.5 Hz, 1H), 6.00-5.93 (m, 1H), 5.39-5.24 (m, 2H), 4.69 (dd, J = 5.0, 1.5 Hz, 2H), 3.94 (d, J = 17.5 Hz, 1H), 3.65 (s, 6H), 3.56 (d, J = 17.5 Hz, 1H), 1.66 (s, 3H). 1-77  [00654] Cl F [00655] 1-78  [00656] Cl F [00657] 1-79  [00658] Cl F [00659] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.97 (d, J = 7.5 Hz, 1H), 7.92 (d, J = 9.5 Hz, 1H), 4.85 (s, 2H), 3.92 (d, J = 17.5 Hz, 1H), 3.58 (d, J = 17.5 Hz, 1H), 3.35 (s, 1H), 1.66 (s, 3H). 1-80  [00660] Cl F [00661] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.95 (d, J = 7.5 Hz, 1H), 7.91 (d, J = 9.5 Hz, 1H), 4.78 (q, J = 2.5 Hz, 2H), 3.89 (d, J = 17.5 Hz, 1H), 3.63 (s, 6H), 3.55 (d, J = 17.5 Hz, 1H), 1.84 (t, J = 2.5 Hz, 3H), 1.63 (s, 3H). 1-81  [00662] Cl F [00663] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.95 (d, J = 7.5 Hz, 1H), 7.91 (d, J = 9.5 Hz, 1H), 4.23 (t, J = 6.5 Hz, 2H), 3.93 (d, J = 18.0 Hz, 1H), 3.64 (s, 6H), 3.56 (d, J = 18.0 Hz, 1H), 2.59-2.55 (m, 2H), 2.09 (s, 1H), 1.65 (s, 3H). 1-82  [00664] Cl F [00665] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.96 (d, J = 7.5 Hz, 1H), 7.93 (d, J = 9.5 Hz, 1H), 5.47-5.42 (m, 1H), 3.91 (d, J = 17.5 Hz, 1H), 3.65-3.62 (m, 7H), 3.56 (d, J = 17.5 Hz, 1H), 1.64 (d, J = 5.0 Hz, 3H), 1.50 (s, 3H). 1-83  [00666] Cl F [00667] .sup.1H NMR (500 MHz, DMSO) δ 7.95-7.92 (m, 2H), 4.18-4.45 (m, 1H), 3.85 (d, J = 17.5 Hz, 1H), 3.64 (s, 6H), 3.52 (d, J = 17.5 Hz, 1H), 1.62 (s, 3H), 1.34-1.20 (m, 1H), 0.74-0.71 (m, 3H). 1-84  [00668] Cl F [00669] .sup.1H NMR (500 MHz, DMSO) δ 7.94-7.90 (m, 2H), 4.01 (d, J = 7.0 Hz, 2H), 3.92 (d, J = 17.5 Hz, 1H), 3.64 (s, 6H), 3.55 (d, J = 17.5 Hz, 1H), 1.65 (s, 3H), 1.15-1.10 (m, 1H), 0.54-0.50 (m, 2H), 0.31-0.28 (m, 2H). 1-85  [00670] Cl F [00671] 1-86  [00672] Cl F [00673] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.97- 7.91 (m, 2H), 6.33 (t, J = 54.0 Hz, 1H), 4.51-4.45 (m, 2H), 4.07-3.92 (m, 1H), 3.64 (s, 6H), 3.34-3.30 (m, 1H), 1.67 (s, 3H). 1-87  [00674] Cl F [00675] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.97 (d, J = 7.5 Hz, 1H), 7.92 (d, J = 9.5 Hz, 1H), 4.97-4.83 (m, 2H), 3.97 (d, J = 17.5 Hz, 1H), 3.65 (s, 6H), 3.35 (d, J = 17.5 Hz, 1H), 1.69 (s, 3H). 1-88  [00676] Cl F [00677] .sup.1H NMR (500 MHz, DMSO) δ 7.95 (d, J = 7.5 Hz, 1H), 7.93 (d, J = 9.5 Hz, 1H), 4.58- 4.49 (m, 2H), 4.26 (t, J = 6.0 Hz, 2H), 3.93 (d, J = 17.5 Hz, 1H), 3.65 (s, 6H), 3.54 (d, J = 17.5 Hz, 1H), 2.08-1.98 (m, 2H), 1.65 (s, 3H). 1-89  [00678] Cl F [00679] .sup.1H NMR (500 MHz, DMSO) δ 7.97 (d, J = 7.5 Hz, 1H), 7.93 (d, J = 9.5 Hz, 1H), 4.48 (t, J = 13.0 Hz, 2H), 3.95 (d, J = 17.5 Hz, 1H), 3.69-3.58 (m, 7H), 1.79-1.59 (m, 6H). 1-90  [00680] Cl F [00681] .sup.1H NMR (500 MHz, DMSO) δ 7.90 (d, J = 9.5 Hz, 1H), 7.88 (d, J = 7.5 Hz, 1H), 4.39 (t, J = 6.0 Hz, 2H), 3.93 (d, J = 17.5 Hz, 1H), 3.62 (s, 6H), 3.56 (d, J = 17.5 Hz, 1H), 2.76-2.74 (m, 2H), 1.64 (s, 3H). 1-91  [00682] Cl F [00683] 1-92  [00684] Cl F [00685] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.94 (d, J = 7.5 Hz, 1H), 7.90 (d, J = 9.5 Hz, 1H), 6.71-6.52 (m, 1H), 6.15-6.09 (m, 1H), 4.87-4.63 (m, 2H), 3.92 (d, J = 17.5 Hz, 1H), 3.63 (s, 6H), 3.54 (d, J = 17.5 Hz, 1H), 1.63 (s, 3H). 1-93  [00686] Cl F [00687] 1-94  [00688] Cl F [00689] .sup.1H NMR (500 MHz, DMSO) δ 7.92 (d, J = 8.0 Hz, 1H), 7.89 (d, J = 9.5 Hz, 1H), 4.10- 4.00 (m, 2H), 3.64 (s, 6H), 3.42-3.36 (m, 1H), 3.26-3.22 (m, 1H), 2.44-2.39 (m, 2H), 2.02-1.92 (m, 2H), 1.40 (s, 3H), 1.19 (t, J = 7.0 Hz, 3H). 1-95  [00690] Cl F [00691] 1-96  [00692] Cl F [00693] .sup.1H NMR (500 MHz, DMSO) δ 7.91-7.90 (m, 2H), 4.07-4.06 (m, 2H), 3.68-3.61 (s, 6H), 3.31 (d, J = 14.5 Hz, 1H), 3.11 (d, J = 14.5 Hz, 1H), 2.35-2.34 (m, 2H), 1.77- 1.53 (m, 4H), 1.39 (s, 3H), 1.19 (t, J = 7.0 Hz, 3H) 1-97  [00694] Cl F [00695] 1-98  [00696] Cl F [00697] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.91 (d, J = 9.5 Hz, 1H), 7.83 (d, J = 7.5 Hz, 1H), 5.10-5.05 (m, 1H),4.55 (d, J = 7.0 Hz, 1H), 4.05 (q, J = 7.0 Hz, 2H), 3.62 (s, 6H), 1.43 (d, J = 6.5 Hz, 3H), 1.00 (t, J = 7.0 Hz, 3H). 1-99  [00698] Cl F [00699] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.01 (d, J = 9.5 Hz, 1H), 7.95 (d, J = 7.5 Hz, 1H), 5.95-5.92 (m, 1H), 5.24 (d, J = 5.0 Hz, 1H), 4.10 (q, J = 8.0 Hz, 2H), 3.65 (s, 6H), 1.04 (t, J = 8.0 Hz, 3H). 1-100 [00700] Cl F [00701] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.97 (d, J = 9.5 Hz, 1H), 7.90 (d, J = 7.5 Hz, 1H), 5.63 (d, J = 5.5 Hz, 1H), 5.14 (d, J = 5.5 Hz, 1H), 4.24 (q, J = 7.0 Hz, 2H), 4.09 (q, J = 7.0 Hz, 2H), 3.64 (s, 6H), 1.27 (t, J = 7.0 Hz, 3H), 1.02 (t, J = 7.0 Hz, 3H). 1-101 [00702] Cl F [00703] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.95 (d, J = 9.5 Hz, 1H), 7.86 (d, J = 7.5 Hz, 1H), 4.21 (q, J = 7.0 Hz, 2H), 4.15 (q, J = 7.5 Hz, 1H), 3.65 (s, 6H), 1.52 (s, 3H), 1.25 (t, J = 7.0 Hz, 3H), 1.04 (d, J = 7.5 Hz, 3H). 1-102 [00704] Cl F [00705] 1-103 [00706] Cl F [00707] 1-104 [00708] Cl F [00709] 1-105 [00710] Cl F [00711] 1-106 [00712] Cl F [00713] 1-107 [00714] Cl F [00715] 1-108 [00716] Cl F [00717] 1-109 [00718] Cl F [00719] 1-110 [00720] Cl F [00721]

[0125] The method for preparing the compound of the invention will be explained in detail in the following program and embodiment. The material is commercial available or prepared through known method reported in the literature or shown in the route. Those skilled in the art should understand that the compound of the invention can also be synthesized by other synthetic route. Although the detailed material and reaction condition in the synthetic route have been explicated in the following text, it is still easy to be replaced by other similar material and condition. Isomer of the compound, for example, that produced with the variation of the preparation method of the present invention is included in the scope of the present invention. In addition, the following preparation method can be further modified according to the disclosures of the present invention by using common chemical method known to those skilled in the art, for example, protection of suitable group in the process of the reaction, etc.

[0126] The following method of application can be used to improve further understanding of the preparation method of the present invention. The specific material, class and condition have been determined to be further explication of the present invention, not to be any limit of the reasonable scope thereof. Reagents of the following synthetic compound showed in the table can either be purchased from the market or easily prepared by those skilled in the art.

[0127] Examples of representative compounds are as follows, the synthesis methods of other compounds are similar, and will not be described in detail here.

1. Synthesis of Compound 55

[0128] (1) Compound 55-1 (1.18 g, 1.0 eq., 10 mmol) was dissolved in THE (30 mL), added with NaH (500 mg, 1.25 eq., 12.5 mmol, 60% purity) under ice-water bath. The mixture was stirred for 30 minutes under ice-water bath, then added with compound 55-2 (1.93 g, 1.0 eq, 10 mmol), slowly returned to room temperature, and stirred at room temperature for 12 hours, the reaction was tracked by TLC until the reaction was completed. After that, the reaction solution was slowly added into water (200 mL) to quench the reaction, then extracted with ethyl acetate (20 mL) for three times. The organic phase was combined, dried with anhydrous sodium sulfate, filtered, and finally concentrated to produce crude compound 55-3 (1.88 g, yield 82%, 8.2 mmol, yellow oily liquid), which was used directly in the next step.

##STR00722##

[0129] (2) Compound a (20 g, 91.5 mmol, 1.0 eq) was added to 150 mL DMF, and the reaction solution was slowly added with NCS (13.4 g, 100.7 mmol, 1.1 eq) at 35° C. After the addition, the solution was stirred at 35° C. for 1.5 hours, it was detected by LCMS that the raw material almost used up. The reaction solution was poured into 100 mL HCl (1M), then extracted by adding dichloromethane, the organic phrase was washed with saturated brine (100 ml*3), then concentrated to produce crude product 55-4 (26 g, crude product, yellow oily liquid), which was used directly for the next step.

##STR00723##

[0130] (3) Compound 55-4 (1.6 g, 6.7 mmol, 1.0 eq) and Et.sub.3N (1.01 g, 10.05 mmol, 1.5 eq) were added to 20 mL DCM. The reaction solution was added with compound 55-3 (1.84 g, 8 mmol, 1.2 eq) at 0° C. and reacted at 0° C. for 1 hour, then the product was detected by LCMS. The reaction solution was added with 100 mL water, and then extracted with dichloromethane (100 ml*3). The organic phrase was dried with anhydrous sodium sulfate and concentrated, the crude product was purified by column chromatography to produce compound 55-5 (1.94 g, yield 65%, 4.35 mmol, yellow solid).

##STR00724##

[0131] (4) Compound 55-5 (1.80 g, 4.0 mmol, 1.0 eq), Fe powder (672 mg, 12.0 mmol, 3 eq), NH.sub.4C.sub.1 (530 mg, 10.0 mmol, 2.0 eq) and water (5 ml) were successively added to 20 mL EtOH. Then after the reaction solution was reacted at 80° C. for 2 hours, it was detected by LCMS that the raw material used up, and the principle peak was the product peak. The reaction solution was filtered with diatomite and concentrated to remove ethanol, and then added with water (100 ml), extracted with ethyl acetate and concentrated to produce black crude product. Such crude product was separated and purified by column chromatography to produce compound 55-6 (1.41 g, yield 85%, 3.4 mmol, yellow solid).

##STR00725##

[0132] (5) Compound 55-6 (1.2 g, 2.89 mmol, 1.0 eq) and compound 55-7 (0.50 g, 3.18 mmol, 1.1 eq) were added to 10 ml toluene, and the reaction solution was heated for 1 hour at 110° C. It was detected by LCMS that the raw material almost used up, the principal peak belonged to the product. After concentrating the solvent, the crude product was separated by column chromatography to produce compound 55-8 (1.29 g, yield 83.4%, 2.41 mmol, yellow solid).

##STR00726##

[0133] (6) Compound 55-9 (0.48 g, 2.1 mmol, 1.5 eq) and AcONa (58 mg, 0.7 mmol, 0.5 eq) were added to 10 ml DMF, and the reaction solution was added with compound 55-8 (0.75 g, 1.4 mmol, 1.0 eq) at 60° C., then reacted at 60° C. for 1 hour. The product was detected by LCMS. The reaction solution was added with water (10 ml) and extracted with ethyl acetate, the organic phase was washed with saturated brine (20 ml*1), after concentrating the organic phase, the crude product was separated by column chromatography to produce compound 55 (0.58 g, yield 72%, 1.0 mmol, yellow solid).

##STR00727##

2. Synthesis of Compound 119

[0134] (1) Diethyl oxalate (5.0 g, 34.2 mmol, 1.0 eq) was dissolved in anhydrous THE (80 mL). The mixture was cooled to −60° C. through dry-ice ethanol bath under nitrogen protection, slowly added dropwise with cyclopropylmagnesium bromide (1M in THF) (37.6 mL, 37.6 mmol, 1.1 eq), then reacted at low temperature for 1 hour, it was detected by LCMS that the raw material almost used up, and a new peak emerged. The reaction solution was heated to room temperature, slowly added dropwise with saturated ammonium chloride aqueous solution to quench the reaction, and diluted with 100 mL water. The aqueous phase was extracted with ethyl acetate (EA, 3×100 mL), and the organic phase was combined, dried with anhydrous sodium sulfate, concentrated under reduced pressure to remove the solvent, the crude product 119-1 was obtained (4.9 g, quantitative), directly used in the next step without purification.

##STR00728##

[0135] (2) Methyltriphenylphosphonium bromide (12.2 g, 34.2 mmol, 1.0 eq) was dissolved in anhydrous THE (100 mL). The mixture was cooled to −60° C. through dry-ice ethanol bath under nitrogen protection, slowly added with LiHMDS (1M in THF) (34.2 mL, 34.2 mmol, 1.0 eq), then reacted at low temperature for 1 hour. The reaction solution was slowly added with the THF solution of product 119-1 (4.9 g, 34.2 mmol, 1.0 eq) obtained from the last step, then reacted at low temperature for 2 hours. It was detected by LCMS that the raw material used up, and a new peak emerged. The reaction solution was heated to room temperature, slowly added dropwise with saturated ammonium chloride aqueous solution to quench the reaction. Most of solvent was removed by concentration under reduced pressure. The residual was diluted with 100 mL water. The aqueous phase was extracted with ether (2×100 mL), and the organic phase was combined, dried with anhydrous sodium sulfate, concentrated under reduced pressure to remove the solvent, the product 119-2 was obtained (3.2 g, crude product yield 67%), directly used in the next step without purification.

##STR00729##

[0136] (3) Raw material 55-4 (2.8 g, 11.4 mmol, 0.5 eq) and Et.sub.3N (1.7 g, 17.1 mmol, 1.5 eq) were added to 60 mL DCM, and the reaction solution was added with product 119-2 (3.2 g, 22.8 mmol, 1.0 eq) obtained from the last step at 0° C., reacted at 0° C. for 1 hour, then the product was detected by LCMS. The reaction solution was added with 50 mL water, then extracted with dichloromethane (50 ml*3). The organic phrase was dried with anhydrous sodium sulfate and concentrated, the crude product was purified by column chromatography to produce compound 119-3 (320 mg, yield 8%, yellow oil).

##STR00730##

[0137] (4) Product 119-3 (320 mg, 0.9 mmol, 1.0 eq) obtained from the last step, Fe powder (151 mg, 2.7 mmol, 3 eq), NH.sub.4C.sub.1 (95 mg, 1.8 mmol, 2 eq) and water (5 ml) were successively added to 20 mL EtOH. After the reaction solution was reacted at 80° C. for 0.5 hour, it was detected by LCMS that the raw material used up, and the principle peak was the product peak. The reaction solution was filtered with diatomite and concentrated to remove ethanol, then added with water (100 ml), extracted with ethyl acetate and concentrated to produce black crude product. Such crude product was separated and purified by column chromatography to produce compound 119-4 (190 mg, yield 65%, yellow oil).

##STR00731##

[0138] (5) Product 119-4 (190 mg, 0.6 mml, 1.0 eq) obtained from the last step, 10 mL acetic acid and raw material 119-5 (125 mg, 0.6 mml, 1.0 eq) were added into a 50 mL round mouth flask. The mixture was heated to 125° C. and reacted for 20 minutes. It was detected by LCMS that the product was formed. The reaction solution was cooled to room temperature, concentrated under reduced pressure to remove acetic acid, the residue was purified through silica gel column chromatography, then concentrated to produce compound 119-6 (160 mg, yield 56%, light-yellow oil).

##STR00732##

[0139] (6) Product 119-6 (160 mg, 0.33 mmol, 1.0 eq) obtained from the last step, potassium carbonate (228 mg, 1.65 mmol, 5.0 eq) and methyl iodide (140 mg, 0.99 mmol, 3.0 eq) was added to 10 mL anhydrous DMF. The mixture was reacted for 3 hours at room temperature. It was detected by LCMS that the raw material used up, and the product was formed. The reaction solution was diluted with ethyl acetate (EA, 60 ml), and the organic phase was washed with water (2×30 mL), then washed with saturated brine (30 mL), dried with anhydrous sodium sulfate, then filtered and concentrated, the crude product was separated and purified by column chromatography to produce compound 119 (100 mg, yield 60%, yellow oil).

##STR00733##

[0140] (7) Compound 119 was subjected to chiral HPLC separation (Chromatographic column type: AD-5H 5 μm 21.2×250 mm; Mobile phase: N-hexane: ethanol=7:3; Flow rate: 20 ml/min; Wavelength: 220 nm) to produce compound 119(S) (liquid purity: 98%, 93% ee).

##STR00734##

3. Synthesis of Compound 206

[0141] (1) Compound 206-1 was prepared by referring to the above preparation method of compound 119-4. Then 10 ml 1,4-dioxane was added with compound 206-1 (0.6 g, 2.0 mmol, 1.0 eq) and 206-2 (0.38 g, 2.2 mmol, 1.1 eq). The reaction solution was heated at 110° C. for 1 hour. It was detected by LCMS that the raw material almost used up, the principal peak belonged to the product. The solvent was concentrated, and the crude product was separated by column chromatography to produce compound 206-3 (0.7 g, yield 83.4%, white solid).

##STR00735##

[0142] (2) Compound 206-4 (0.47 g, 2.1 mmol, 1.5 eq) and AcONa (58 mg, 0.7 mmol, 0.5 eq) was added to 10 ml DMF. The reaction solution was added with 206-3 (0.6 g, 1.4 mmol, 1.0 eq) at 60° C., then reacted at 60° C. for 1 hour. The product was detected by LCMS. The reaction solution was added with water (10 ml), then extracted with ethyl acetate. The organic phase was washed with saturated brine (20 ml*1), then concentrated, the crude product was separated by column chromatography to produce compound 206 (0.4 g, yield 61.4%, white solid).

##STR00736##

4. Synthesis of Compound 229

[0143] (1) Compound 55-4 (2 g, 7.94 mmol, 1.0 eq) and Et.sub.3N (1.2 g, 11.88 mmol, 1.5 eq) was added to 200 ml DCM. The reaction solution was then added with compound 229-1 (1.02 g, 7.97 mmol, 1.0 eq) at 0° C., slowly heated to 20° C. and reacted for 2-4 hours, the product was detected by LCMS. The reaction solution was added with 100 ml water, extracted with dichloromethane (50 ml*3). The organic phase was dried with anhydrous sodium sulfate and then concentrated, the crude product was purified by column chromatography to produce compound 229-2 (860 mg, yield 32%).

##STR00737##

[0144] (2) Compound 229-2 (860 mg, 2.5 mmol, 1.0 eq), Fe powder (420 mg, 7.5 mmol, 3.0 eq), NH.sub.4C.sub.1 (265 mg, 5.0 mmol, 2 eq) and water (12.5 ml) was successively added to 50 mL EtOH. After the reaction solution was reacted at 80° C. for 2 hours, it was detected by LCMS that the raw material used up, the principal peak belonged to the product. The reaction solution was cooled, filtered with diatomite, concentrated to remove EtOH, then added with water, extracted with ethyl acetate and concentrated to produce black crude product 229-3 (720 mg, yield 90%), which was directly used in the next step.

##STR00738##

[0145] (3) Compound 229-3 (450 mg, 1.43 mmol, 1.0 eq), DMAP (17 mg, 0.14 mmol, 0.01 eq), triethylamine (217 mg, 2.15 mmol, 1.5 eq) and thiocarbonyldiimidazole CDI-S (306 mg, 1.72 mmol, 1.2 eq) were added to 20 ml toluene. The reaction solution was reacted at room temperature for 1 hour. After toluene was removed by rotary evaporation, added with water and extracted with ethyl acetate, the organic phase was mixed with silica gel, the crude product was purified by column chromatography to produce compound 229-4 (270 mg, yield 53%).

##STR00739##

[0146] (4) Compound 229-4 (270 mg, 0.76 mmol, 1.0 eq), cesium carbonate (739 mg, 2.27 mmol, 3.0 eq) and compound 229-5 (153 mg, 0.84 mmol, 1.1 eq) were added to 10 ml DMF. After the reaction solution was stirred at 0° C. for 2-3 hours, it was detected by LCMS that the raw material used up, the principal peak belonged to the product. The reaction solution was added with water, extracted with ethyl acetate, and washed with saturated brine. The organic phase was mixed with silica gel, and the crude product was purified by column chromatography to produce 229-6 (102 mg, yield 27%).

##STR00740##

[0147] (5) Compound 229-6 (102 mg, 0.21 mmol, 1.0 eq), methyl iodide (118 mg, 0.83 mmol, 4.0 eq) and potassium carbonate (57 mg, 0.41 mmol, 2.0 eq) were successively added to 10 mL DMF. The reaction solution was reacted for 4-6 hours at 25-30° C. depending on LCMS detection until the reaction was completed. The reaction solution was added with water, extracted with ethyl acetate, and washed with saturated brine. The organic phase was mixed with silica gel, and the crude product was purified by column chromatography to produce 229 (70 mg, yield 77%).

##STR00741##

5. Synthesis of Compound 1-62

[0148] (1) Compound 1-62-1 was prepared by referring to the above synthesis method of compound 229-3. Then compound 1-62-1 (0.6 g, 2.0 mmol, 1.0 eq) and phenyl chloroformate (0.34 g, 2.2 mmol, 1.1 eq) were added to 10 ml toluene. The reaction solution was heated at 110° C. for 1 hour. It was detected by LCMS that the raw material almost used up, the principal peak belonged to the product. The solvent was concentrated, and the crude product was separated by column chromatography to produce compound 1-62-2 (0.7 g, yield 83.4%, white solid).

##STR00742##

[0149] (2) Compound 206-4 (0.48 g, 2.1 mmol, 1.5 eq) and AcONa (58 mg, 0.7 mmol, 0.5 eq) were added to 10 ml DMF. The reaction solution was added with compound 1-62-2 (0.6 g, 1.4 mmol, 1.0 eq) at 60° C., then reacted at 60° C. for 1 hour. The product was detected by LCMS. The reaction solution was added with water (10 ml), then extracted with ethyl acetate. The organic phase was washed with saturated brine (20 ml*1), then concentrated, the crude product was separated by column chromatography to produce 1-62-racemate (0.4 g, yield 61.4%, white solid).

##STR00743##

[0150] (3) Compound 1-62-racemate (0.5 g, 98% purity) was subjected to chiral HPLC separation (Column: AD-5H; Column Size: 3 cm×25 cm, 5 um; Injection: 2.0 ml; Mobile phase: Hex:i-PrOH(20% EtOH)=6:4; Flow rate: 20 ml/min; Wavelength: UV 254 nm; Temperature: 25° C.; Sample solution: 50 mg/2 ml in EtOH; Run time=60 mins), then concentrated to produce compound 1-62 (0.16 g, Rt=10.51 min, 100% ee, white solid) and 1-62-R configuration (0.13 g, Rt=30.81 min 99.8% ee, white solid).

##STR00744##

[0151] Biological Activity Evaluation:

[0152] The activity level criteria for plant damage (i.e., growth control rate) are as follows:

[0153] Level 5: growth control rate is above 85%;

[0154] Level 4: growth control rate is greater than or equal to 60% and less than 85%;

[0155] Level 3: growth control rate is greater than or equal to 40% and less than 60%;

[0156] Level 2: growth control rate is greater than or equal to 20% and less than 40%;

[0157] Level 1: growth control rate is greater than or equal to 5% and less than 20%;

[0158] Level 0: growth control rate is less than 5%.

[0159] The above growth control rates are fresh weight control rates.

[0160] Experiment on weeding effect in post-emergence stage:

[0161] Monocotyledonous and dicotyledonous weed seeds (Descurainia sophia, Capsella bursa-pastoris, Abutilon theophrasti, Galium aparine, Stellaria media, Lithospermum arvense, rorippa indica, Alopecurus aequalis, Alopecurus japonicus, Beckmannia syzigachne, Sclerochloa dura, Conyza Canadensis, Phleum paniculatum, Veronica didyma Tenore, Bromus japonicus, Aegilops tauschii, Phalaris arundinacea, Amaranthus retroflexus, Chenopodium album, Commelina communis, Sonchus arvensis, Convolvulus arvensis, Cirsium setosum, Solanum nigrum, Acalypha australis, Digitaria sanguinalis, Echinochloa crusgalli, Setaria viridis, Setaria glauca, Leptochloa chinensis, Monochoria vaginalis, Sagittaria trifolia, Scirpus juncoides, Cyperus rotundus, Cyperus iria, Cyperus difformis, Fimbristylis, Portulaca oleracea, Xanthium sibiricum, Pharbitis nil, Conyza japonica, etc.) and major crop seeds (wheat, corn, rice, soybean, cotton, oilseed rape, millet, sorghum, potato, sesame, ricinus, etc.) were placed in plastic pots filled with soil, then covered with 0.5-2 cm of soil, allowed to grow in a good greenhouse environment. After 2 weeks of sowing, the test plants were treated in the 2-3 leaf stage. The tested compounds of the present invention were respectively dissolved in acetone, then added with Tween 80 and 1.5 liter/ha of emulsifiable concentrate of methyl oleate as synergist, diluted with a certain amount of water to obtain a solution with a certain concentration, and sprayed with a spray tower onto the plants. After the application, the plants were cultured for 3 weeks in the greenhouse, and then the experimental results of the weeding were counted. The doses of the used compounds were 500, 250, 125, 60, 15, 7.5 g a.i./ha, and the averages were obtained by repeating for three times. Representative data are listed in Tables 2-6.

TABLE-US-00003 TABLE 2 Results on weeding effect in post-emergence stage Com- Dose pound Alopecurus Beckmannia Rorippa Conyza (g NO. japonicus syzigachne indica japonica a.i./ha)  3 5 5 5 5 125  3(S) 5 5 5 5 125  4 5 5 5 5 125  4(S) 5 5 5 5 125  5 5 5 5 5 125  6 5 5 5 5 125  17 5 5 5 5 125  17(S) 5 5 5 5 125  26 5 5 5 5 125  31 5 5 5 5 125  33 5 5 5 5 125  34 5 5 5 5 125  34(S) 5 5 5 5 125  35 5 5 5 5 125  43 5 5 5 5 125  53 5 5 5 5 125  54 5 5 5 5 125  55 5 5 5 5 125  56 5 5 5 5 125  59 5 5 5 5 125 203 5 5 5 5 125 204 5 5 5 5 125 205 5 5 5 5 125 206 5 5 5 5 125

TABLE-US-00004 TABLE 3 Results of comparison experiment on weeding effect in post-emergence stage Com- Dose pound Alopecurus Beckmannia Rorippa Conyza (g No. japonicus syzigachne indica japonica a.i./ha)  3 5 5 5 5 15  3(S) 5 4 5 4 7.5  4 5 4 5 4 15  4(S) 5 5 5 5 15  5 5 4 5 4 15  6 5 5 5 5 15  17 5 5 5 5 15  26 5 5 5 5 15  31(S) 5 5 5 5 15  33(S) 5 5 5 5 15  34 5 5 5 5 15  35 N N 5 4 15  43 N N 5 4 15  53 N N 5 5 15  54(S) 5 5 5 5 15  55(S) 5 5 5 5 15  56(S) 5 5 5 5 15  59(S) 5 5 5 5 15 203 N N 5 4 15 204(S) 5 5 5 5 15 205(S) 5 5 5 5 15 206(S) 5 5 5 5 15 Control 3 2 2 2 15 compound A

TABLE-US-00005 TABLE 4 Results on weeding effect in post-emergence stage Com- Dose pound Alopecurus Beckmannia Rorippa Conyza (g No. japonicus syzigachne indica japonica a.i./ha) 105 5 5 5 5 125 105(S) 5 5 5 5 125 119 5 5 5 5 125 119(S) 5 5 5 5 125 126 5 5 5 5 125 129 5 5 5 5 125 132 5 5 5 5 125 134 5 5 5 5 125 135 5 5 5 5 125 136 5 5 5 5 125 142 5 5 5 5 125 152 5 5 5 5 125 218 5 5 5 5 125 219 5 5 5 5 125 220 5 5 5 5 125 226 5 5 5 5 125 228 5 5 5 5 125 228(S) 5 5 5 5 125 229 5 5 5 5 125 230 5 5 5 5 125 231 5 5 5 5 125

TABLE-US-00006 TABLE 5 Results of comparison experiment on weeding effect in post-emergence stage Com- Dose pound Alopecurus Beckmannia Rorippa Conyza (g No. japonicus syzigachne indica japonica a.i./ha) 105 5 5 5 5 15 119 5 5 5 5 15 119(S) 5 5 4 4 7.5 126(S) 5 5 5 5 15 129(S) 5 5 5 5 15 132(S) 5 5 5 5 15 134(S) 5 5 5 5 15 135(S) 5 5 5 5 15 136(S) 5 5 5 5 15 142(S) 5 5 5 5 15 152(S) 5 5 5 5 15 218(S) 5 5 5 5 15 219 N N 4 N 15 220(S) 5 5 5 5 15 226(S) 5 5 5 5 15 228 5 4 5 5 15 229(S) 5 5 5 5 15 230(S) 5 5 5 5 15 231 N 4 5 5 15 Control 4 3 3 4 15 compound B Control 3 2 2 3 7.5 compound B

TABLE-US-00007 TABLE 6 Results of comparison experiment on weeding effect in post-emergence stage Alopecurus Beckmannia Rorippa Conyza Dose Compound No. japonicus syzigachne indica japonica (g a.i./ha) 1-2  5 5 5 5 15 1-9  5 5 5 5 15 1-37  5 5 5 5 15 1-39  5 5 5 5 15 Control compound B 4 3 3 4 15 [00745] 2 1 1 1 15 1-55  5 5 5 5 15 1-60  5 5 5 5 15 1-61  5 5 5 5 15 1-62  5 5 5 5 15 1-63  5 5 5 5 15 1-64  5 5 5 5 15 1-65  5 5 5 5 15 1-66  5 5 5 5 15 1-67  5 5 5 5 15 1-68  5 5 5 5 15 1-69  5 5 5 5 15 1-70  5 5 5 5 15 1-71  5 5 5 5 15 1-72  5 5 5 5 15 1-73  5 5 5 5 15 1-74  5 5 5 5 15 1-75  5 5 5 5 15 1-76  5 5 5 5 15 1-79  5 5 5 5 15 1-80  5 5 5 5 15 1-81  5 5 5 5 15 1-82  5 5 5 5 15 1-83  5 5 5 5 15 1-84  5 5 5 5 15 1-86  5 5 5 5 15 1-87  5 5 5 5 15 1-88  5 5 5 5 15 1-89  5 5 5 5 15 1-90  5 5 5 5 15 1-92  5 5 5 5 15 1-94  5 5 5 5 15 1-96  5 5 5 5 15 1-98  5 5 5 5 15 1-99  5 5 5 5 15 1-100 5 5 5 5 15 1-101 5 5 5 5 15 Control compound A 3 2 2 2 15 [00746] 2 1 1 1 15 Note: N represents no data; Control compound A: [00747]Control compound B: [00748]

[0162] Experiment on Weed Effect in Pre-Emergence Stage:

[0163] The seeds of monocotyledonous and dicotyledonous weeds and main crops (wheat, corn, rice, soybean, cotton, oilseed rape, millet and sorghum) were put into a plastic pot loaded with soil and covered with 0.5-2 cm soil. The test compounds of the present invention was dissolved with acetone, then added with tween 80, diluted by a certain amount of water to reach a certain concentration, and sprayed immediately after sowing. The obtained seeds were incubated for 4 weeks in the greenhouse after spraying and the test results were observed. It was observed that the herbicide mostly had excellent effect at the application rate of 250 g a.i./ha, especially to weeds such as Echinochloa crusgalli, Digitaria sanguinalis and Abutilon theophrasti, etc.. And many compounds had good selectivity for corn, wheat, rice, and soybean.

[0164] It is indicated from the experiment of main weeds in wheat and rice fields that the compound of the present invention generally have good weed control efficacy. Above all, it is noted that the compound of the invention have extremely high activity to broad-leaved weeds and cyperaceae weeds, which are resistant to ALS inhibitor, like Sagittaria trifolia, Scirpus juncoides, Cyperus difformis, Descurainia sophia, Capsella bursa-pastoris, Lithospermum arvense, Galium aparineL., and Cyperus rotundusL., etc., and have excellent commercial value.

[0165] Transplanted Rice Safety Evaluation and Weed Control Effect Evaluation in Rice Field:

[0166] Rice field soil was loaded into a 1/1,000,000 ha pot. The seeds of Echinochloa crusgalli, Scirpus juncoides, and Bidens tripartitaL. were sowed and gently covered with soil, then left to stand still in greenhouse in the state of 0.5-1 cm of water storage. The tuber of Sagittaria trifolia was planted in the next day or 2 days later. It was kept at 3-4 cm of water storage thereafter. The weeds were treated by dripping the WP or SC water diluents prepared according to the common preparation method of the compounds of the present invention with pipette homogeneously to achieve specified effective amount when Echinochloa crusgalli, Scirpus juncoides, and Bidens tripartita L. reached 0.5 leaf stage and Sagittaria trifolia reached the time point of primary leaf stage.

[0167] In addition, the rice field soil that loaded into the 1/1,000,000 ha pot was leveled to keep water storage at 3-4 cm depth. The 3 leaf stage rice (japonica rice) was transplanted at 3 cm of transplanting depth the next day. The compound of the present invention was treated by the same way after 5 days of transplantation.

[0168] The fertility condition of Echinochloa crusgalli, Scirpus juncoides, Bidens tripartitaL. and Sagittaria trifolia 14 days after the treatment of the compound of the invention and the fertility condition of rice 21 days after the treatment of the compound of the invention respectively with the naked eye. Evaluate the weed control effect with the above activity standard level. Many compounds show excellent activity and selectivity.

[0169] Note: The seeds of Echinochloa crusgalli, Scirpus juncoides and Bidens tripartita L. were collected from Heilongjiang Province of China. The tests indicated that the weeds were resistant to the common doses of Pyrazosulfuron-ethyl.

[0170] At the same time, it is found after several tests that the compounds and compositions of the present invention have good selectivity to many gramineae grasses such as zoysia japonica, bermuda grass, tall fescue, bluegrass, ryegrass and seashore paspalum etc, and are able to control many important grass weeds and broad-leaved weeds. The compounds also show excellent selectivity and commercial value in the tests on sugarcane, soybean, cotton, oil sunflower, potato, orchards and vegetables in different herbicide application methods.