A cycloalkenamide compound and its application

Abstract

The present invention discloses a cycloalkenamide compound for use as a herbicide. The compound is represented by the general formula (I): #imgabs0#. The substituents in the general formula I are defined as described in the specification. The compound of the general formula I has excellent herbicidal activity and can be used to control agricultural weeds.

Description

Technical Field

[0001] The present invention belongs to the field of herbicides. Specifically, it is a cycloalkenamide compound and its application as a herbicide. Background Art

[0002] Due to the succession and change of weed populations, the emergence and rapid development of resistance to chemical pesticides, the continuous strengthening of people's awareness of ecological environment protection, the increasing understanding of chemical pesticide pollution, the impact of pesticides on non-target organisms, and the increasing attention to the fate of pesticides in the ecological environment. With the gradual reduction of the world's cultivated land area, the continuous growth of the population, and the increasing demand for food, people are forced to rapidly develop agricultural production technologies, improve and perfect farming systems, and continuously invent new and improved herbicidal compounds and compositions.

[0003] CN108290846A reports that certain benzamide compounds have herbicidal activity, such as compound No. 13 - 30 (KC) among them:

[0004]

[0005] The cycloalkenamide compounds as shown in the present invention have not been disclosed. Summary of the Invention

[0006] The object of the present invention is to provide a cycloalkenamide compound with a novel structure and safe for crops and its application as a herbicide.

[0007] To achieve the above object, the technical solution of the present invention is as follows:

[0008] A cycloalkenamide compound, the compound is shown in the general formula I:

[0009]

[0010] In the formula:

[0011] X1 is selected from hydrogen, cyano, nitro, halogen, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C1-C6 alkanesulfinyl, C1-C6 haloalkanesulfinyl, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkoxyC1-C3 alkyl, C1-C6 alkoxyC1-C3 alkoxy, C1-C6 alkoxyC1-C3 alkoxyC1-C3 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C3 alkyl, C3-C6 cycloalkylC1-C3 alkoxy, C3-C6 cycloalkyloxy, C2-C6 alkenyl, C2-C6 alkynyl, C2-C6 alkenylsulfonyl, C2-C6 alkynylsulfonyl, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C2-C6 alkenylthio, C2-C6 alkynylthio, phenyl, phenyloxy, phenylthio, phenylsulfonyl, 5-7 membered aliphatic heterocycles containing 1-4 heteroatoms, 5-7 membered aromatic heterocycles containing 1-4 heteroatoms, 5-7 membered aliphatic heterocycles containing 1-4 heteroatomsC1-C6 alkyl or 5-7 membered aromatic heterocycles containing 1-4 heteroatomsC1-C6 alkyl, and the hydrogen on the phenyl, aliphatic heterocycle, aromatic heterocycle may be substituted by one or more of the following substituents, the substituents being selected from nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy or C3-C6 cycloalkyl;

[0012] W is selected from N or CX2;

[0013] X2 is selected from hydrogen, cyano, nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 halocycloalkyl C1-C6 alkyl, Y1 oxy, Y1 thio, Y1Y2 amino, Y1 sulfinyl, Y1 sulfonyl, Y1 oxy C1-C6 alkyl, Y1 thio C1-C6 alkyl, Y1Y2 amino C1-C6 alkyl, Y1 sulfinyl C1-C6 alkyl, Y1 sulfonyl C1-C6 alkyl, C(O)Y1, C(O)OY1, OC(O)OY1, N(Y1)C(O)OY2, C(O)N(Y1)Y2, N(Y1)C(O)N(Y1)Y2, OC(O)N(Y1)Y2, C(O)N(Y1)OY2, N(Y1)S(O)2Y2, N(Y1)C(O)Y2, OS(O)2Y1, CH=NOY1, C1-C6 alkyl-CH=NOY1, C1-C6 alkyl-O-N=C(Y1)Y2, phenyl, 5- to 7-membered aliphatic heterocycle containing 1 to 4 heteroatoms, 5- to 7-membered aromatic heterocycle containing 1 to 4 heteroatoms, 5- to 7-membered aliphatic heterocycle C1-C6 alkyl or 5- to 7-membered aromatic heterocycle C1-C6 alkyl containing 1 to 4 heteroatoms, and the hydrogen on the phenyl, aliphatic heterocycle, and aromatic heterocycle may be substituted by one or more of the following substituents, and the substituents are selected from nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkoxy, C2-C6 alkenyl, C2-C6 alkynyl, phenyl or halophenyl;

[0014] Y1 and Y2 are each independently selected from C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, phenyl, 5- to 7-membered aliphatic heterocycle containing 1 to 4 heteroatoms, 5- to 7-membered aromatic heterocycle containing 1 to 4 heteroatoms, 5- to 7-membered aliphatic heterocycle C1-C6 alkyl or 5- to 7-membered aromatic heterocycle C1-C6 alkyl containing 1 to 4 heteroatoms, and the hydrogen on the phenyl, aliphatic heterocycle, and aromatic heterocycle may be substituted by one or more of the following substituents, and the substituents are selected from nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkoxy, C2-C6 alkenyl, C2-C6 alkynyl, phenyl or halophenyl;

[0015] X3 is selected from hydrogen, cyano, nitro, halogen, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C1-C6 alkanesulfinyl, C1-C6 haloalkanesulfinyl, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkoxy-C1-C3 alkyl, C1-C6 alkoxy-C1-C3 alkoxy, C1-C6 alkoxy-C1-C3 alkoxy-C1-C3 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C3 alkyl, C3-C6 cycloalkyl-C1-C3 alkoxy, C3-C6 cycloalkyloxy, C2-C6 alkenyl, C2-C6 alkynyl, C2-C6 alkenylsulfonyl, C2-C6 alkynylsulfonyl, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C2-C6 alkenylthio, C2-C6 alkynylthio, phenyl, phenyloxy, phenylthio, phenylsulfonyl, 5-7-membered aliphatic heterocycle containing 1-4 heteroatoms, 5-7-membered aromatic heterocycle containing 1-4 heteroatoms, 5-7-membered aliphatic heterocycle-C1-C6 alkyl containing 1-4 heteroatoms or 5-7-membered aromatic heterocycle-C1-C6 alkyl containing 1-4 heteroatoms, and the hydrogen on the phenyl, aliphatic heterocycle, aromatic heterocycle may be substituted by one or more of the following substituents, and the substituents are selected from nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy or C3-C6 cycloalkyl;

[0016] Q is selected from Q1, Q2, Q3, Q4, Q5 or Q6 groups;

[0017]

[0018] R1, R2, R3 are each independently selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or phenyl;

[0019] R4, R5, R6 are each independently selected from hydrogen, halogen, cyano, nitro, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C1-C6 alkanesulfinyl, C1-C6 haloalkanesulfinyl, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C3 alkoxy-C1-C3 alkyl, C1-C6 alkoxy-C1-C3 alkoxy, C1-C6 alkoxy-C1-C3 alkoxy-C1-C3 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C3 alkyl, C3-C6 cycloalkyl-C1-C3 alkoxy or C3-C6 cycloalkyloxy;

[0020] Z is selected from C3-C8 cycloalkenyl, and the hydrogen on the ring can be substituted by the following substituents, which are selected from nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkenyl or C3-C6 cycloalkyl;

[0021] For the preferred compound, in general formula I:

[0022] X1 is selected from hydrogen, cyano, nitro, halogen, C1-C6 alkylsulfonyl, C1-C6 alkylsulfinyl, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 alkoxyC1-C3 alkyl, C1-C6 alkoxyC1-C3 alkoxy, C1-C6 alkoxyC1-C3 alkoxyC1-C3 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C3 alkyl, C3-C6 cycloalkylC1-C3 alkoxy, C3-C6 cycloalkyloxy, C2-C6 alkenyloxy, C2-C6 alkenyl, C2-C6 alkynyl, phenyl, phenylsulfonyl, phenyloxy, 5-7 membered aliphatic heterocycles containing 1-4 heteroatoms, 5-7 membered aromatic heterocycles containing 1-4 heteroatoms, and the hydrogen on the phenyl, aliphatic heterocycle, aromatic heterocycle can be substituted by one or more of the following substituents, which are selected from nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy or C3-C6 cycloalkyl;

[0023] W is selected from N or CX2;

[0024] X2 is selected from hydrogen, cyano, nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 halocycloalkyl C1-C6 alkyl, Y1 oxy, Y1 thio, Y1Y2 amino, Y1 sulfinyl, Y1 sulfonyl, Y1 oxy C1-C6 alkyl, Y1 thio C1-C6 alkyl, Y1Y2 amino C1-C6 alkyl, Y1 sulfinyl C1-C6 alkyl, Y1 sulfonyl C1-C6 alkyl, C(O)Y1, C(O)OY1, OC(O)OY1, N(Y1)C(O)OY2, C(O)N(Y1)Y2, N(Y1)C(O)N(Y1)Y2, OC(O)N(Y1)Y2, C(O)N(Y1)OY2, N(Y1)S(O)2Y2, N(Y1)C(O)Y2, OS(O)2Y1, CH=NOY1, C1-C6 alkyl-CH=NOY1, C1-C6 alkyl-O-N=C(Y1)Y2, phenyl, a 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aliphatic heterocycle C1-C6 alkyl or a 5-7 membered aromatic heterocycle C1-C6 alkyl, and the hydrogen on the phenyl, aliphatic heterocycle, aromatic heterocycle may be substituted by one or more of the following substituents, and the substituents are selected from nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkyl or C3-C6 cycloalkoxy;

[0025] Y1 and Y2 are each independently selected from C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkyl, phenyl, a 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aliphatic heterocycle C1-C6 alkyl or a 5-7 membered aromatic heterocycle C1-C6 alkyl, and the hydrogen on the phenyl, aliphatic heterocycle, aromatic heterocycle may be substituted by one or more of the following substituents, and the substituents are selected from nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkyl or C3-C6 cycloalkoxy;

[0026] X3 is selected from hydrogen, cyano, nitro, halogen, C1-C6 alkylsulfonyl, C1-C6 alkanesulfinyl, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 alkoxy-C1-C3 alkyl, C1-C6 alkoxy-C1-C3 alkoxy, C1-C6 alkoxy-C1-C3 alkoxy-C1-C3 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C3 alkyl, C3-C6 cycloalkyl-C1-C3 alkoxy, C3-C6 cycloalkyloxy, C2-C6 alkenyloxy, C2-C6 alkenyl, C2-C6 alkynyl, phenyl, phenylsulfonyl, phenyloxy, 5-7 membered aliphatic heterocycles containing 1-4 heteroatoms, 5-7 membered aromatic heterocycles containing 1-4 heteroatoms, wherein the hydrogen on the phenyl, aliphatic heterocycle, aromatic heterocycle can be substituted by one or more of the following substituents, and the following substituents are selected from nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy or C3-C6 cycloalkyl;

[0027] Q is selected from Q1, Q2, Q3, Q4 or Q5 groups;

[0028]

[0029] R1, R2, R3 are each independently selected from hydrogen, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl or phenyl;

[0030] R4 and R5 are each independently selected from hydrogen, halogen, C1-C6 alkylthio, C1-C6 alkyl, C1-C6 alkoxy, C1-C3 alkoxy-C1-C3 alkyl, C1-C6 alkoxy-C1-C3 alkoxy, C1-C6 alkoxy-C1-C3 alkoxy-C1-C3 alkyl or C3-C6 cycloalkyl;

[0031] Z is selected from C3-C8 cycloalkenyl, and the hydrogen on the ring can be substituted by the following substituents, and the following substituents are selected from nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkenyl or C3-C6 cycloalkyl.

[0032] Further preferably, in the compound of general formula I:

[0033] X1 is selected from hydrogen, cyano, nitro, halogen, C1-C3 alkylsulfonyl, C1-C3 alkanesulfinyl, C1-C3 alkylthio, C1-C3 haloalkylthio, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 alkoxyC1-C3 alkyl, C1-C3 alkoxyC1-C3 alkoxy, C1-C3 alkoxyC1-C3 alkoxyC1-C3 alkyl, C3-C6 cycloalkyl or C3-C6 cycloalkyloxy;

[0034] W is selected from N or CX2;

[0035] X2 is selected from hydrogen, cyano, nitro, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C3 alkyl, C3-C6 halocycloalkylC1-C3 alkyl, Y1 oxy, Y1 thio, Y1Y2 amino, Y1 sulfinyl, Y1 sulfonyl, Y1 oxyC1-C3 alkyl, Y1 thioC1-C3 alkyl, Y1Y2 aminoC1-C3 alkyl, Y1 sulfinylC1-C3 alkyl, Y1 sulfonylC1-C3 alkyl, C(O)Y1, C(O)OY1, OC(O)OY1, N(Y1)C(O)OY2, C(O)N(Y1)Y2, N(Y1)C(O)N(Y1)Y2, OC(O)N(Y1)Y2, C(O)N(Y1)OY2, N(Y1)S(O)2Y2, N(Y1)C(O)Y2, OS(O)2Y1, CH=NOY1, C1-C6 alkyl-CH=NOY1, C1-C6 alkyl-O-N=C(Y1)Y2, phenyl, a 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aliphatic heterocycleC1-C3 alkyl or a 5-7 membered aromatic heterocycleC1-C3 alkyl, wherein the hydrogen on the phenyl, aliphatic heterocycle, aromatic heterocycle may be substituted by one or more of the following substituents, and the substituents are selected from nitro, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C3-C6 cycloalkyl or C3-C6 cycloalkyloxy;

[0036] Y1 and Y2 are each independently selected from C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkyl, phenyl, 5-7 membered heteroalicyclic ring containing 1-4 heteroatoms, 5-7 membered heteroaromatic ring containing 1-4 heteroatoms, 5-7 membered heteroalicyclic ring C1-C6 alkyl containing 1-4 heteroatoms or 5-7 membered heteroaromatic ring C1-C6 alkyl containing 1-4 heteroatoms, and the hydrogen on the phenyl, heteroalicyclic ring or heteroaromatic ring may be substituted by one or more of the following substituents, and the substituents are selected from nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkyl or C3-C6 cycloalkoxy;

[0037] X3 is selected from hydrogen, cyano, nitro, halogen, C1-C3 alkylsulfonyl, C1-C3 alkylsulfinyl, C1-C3 alkylthio, C1-C3 haloalkylthio, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 alkoxy C1-C3 alkyl, C1-C3 alkoxy C1-C3 alkoxy, C1-C3 alkoxy C1-C3 alkoxy C1-C3 alkyl, C3-C6 cycloalkyl or C3-C6 cycloalkyloxy;

[0038] Q is selected from Q1, Q2, Q3 or Q4 groups;

[0039]

[0040] R1 and R2 are each independently selected from hydrogen, C1-C6 alkyl, C2-C6 alkenyl or phenyl;

[0041] R3 and R4 are each independently selected from hydrogen, halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C3 alkoxy C1-C3 alkyl, C1-C6 alkoxy C1-C3 alkoxy or C3-C6 cycloalkyl;

[0042] Z is selected from C5-C6 cycloalkenyl, and the hydrogen on the ring may be substituted by the following substituents, and the following substituents are selected from C1-C6 alkyl, C1-C6 alkoxy or C1-C6 alkenyl.

[0043] Further preferably, in the compound of general formula I:

[0044] X1 is selected from hydrogen, cyano, nitro, halogen, C1-C3 alkylsulfonyl, C1-C3 alkylthio, C1-C3 haloalkylthio, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 alkoxy C1-C3 alkyl, C1-C3 alkoxy C1-C3 alkoxy or C1-C3 alkoxy C1-C3 alkoxy C1-C3 alkyl;

[0045] W is selected from N or CX2;

[0046] X2 is selected from hydrogen, cyano, nitro, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 halocycloalkyl C1-C3 alkyl, Y1 oxy, Y1 thio, Y1Y2 amino, Y1 sulfinyl, Y1 sulfonyl, Y1 oxy C1-C3 alkyl, Y1 thio C1-C3 alkyl, Y1Y2 amino C1-C3 alkyl, Y1 sulfinyl C1-C3 alkyl, Y1 sulfonyl C1-C3 alkyl, C(O)Y1, C(O)OY1, OC(O)OY1, N(Y1)C(O)OY2, C(O)N(Y1)Y2, N(Y1)C(O)N(Y1)Y2, OC(O)N(Y1)Y2, C(O)N(Y1)OY2, N(Y1)S(O)2Y2, N(Y1)C(O)Y2, OS(O)2Y1, CH=NOY1, C1-C6 alkyl-CH=NOY1, C1-C6 alkyl-O-N=C(Y1)Y2, phenyl, a 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aliphatic heterocycle C1-C3 alkyl or a 5-7 membered aromatic heterocycle C1-C3 alkyl, the hydrogen on the phenyl, aliphatic heterocycle, aromatic heterocycle can be substituted by one or more of the following substituents, the substituents are selected from nitro, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C3-C6 cycloalkyl or C3-C6 cycloalkoxy;

[0047] Y1 and Y2 are each independently selected from C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkyl, phenyl, a 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aliphatic heterocycle C1-C6 alkyl or a 5-7 membered aromatic heterocycle C1-C6 alkyl, the hydrogen on the phenyl, aliphatic heterocycle, aromatic heterocycle can be substituted by one or more of the following substituents, the substituents are selected from nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkyl or C3-C6 cycloalkoxy;

[0048] Q is selected from the Q1, Q2, Q3 or Q4 group;

[0049]

[0050] R1 and R2 are each independently selected from hydrogen, C1-C3 alkyl or C2-C6 alkenyl;

[0051] R3 and R4 are each independently selected from hydrogen, halogen, C1-C3 alkyl or C1-C3 alkoxy;

[0052] Z is selected from C5-C6 cycloalkenyl, and the hydrogen on the ring can be substituted by the following substituents, and the following substituents are selected from C1-C3 alkyl, C1-C3 alkoxy or C1-C6 alkenyl.

[0053] For the more preferred compound, in general formula I:

[0054] X1 is selected from hydrogen, cyano, nitro, halogen, C1-C3 alkylsulfonyl, C1-C3 alkyl or C1-C3 haloalkyl;

[0055] W is selected from N or CX2;

[0056] X2 is selected from hydrogen, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 halocycloalkyl C1-C3 alkyl, Y1 oxy, Y1 thio, Y1Y2 amino, Y1 sulfonyl, Y1 oxy C1-C3 alkyl, Y1 thio C1-C3 alkyl, Y1Y2 amino C1-C3 alkyl, Y1 sulfonyl C1-C3 alkyl, C(O)Y1, C(O)OY1, OC(O)OY1, N(Y1)C(O)OY2, C(O)N(Y1)Y2, N(Y1)C(O)N(Y1)Y2, OC(O)N(Y1)Y2, C(O)N(Y1)OY2, N(Y1)S(O)2Y2, N(Y1)C(O)Y2, OS(O)2Y1, CH=NOY1, C1-C6 alkyl-CH=NOY1, C1-C6 alkyl-O-N=C(Y1)Y2, phenyl, 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, 5-7 membered aliphatic heterocycle C1-C3 alkyl or 5-7 membered aromatic heterocycle C1-C3 alkyl containing 1-4 heteroatoms, and the hydrogen on the phenyl, aliphatic heterocycle and aromatic heterocycle can be substituted by one or more of the following substituents, and the substituents are selected from nitro, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C3-C6 cycloalkyl or C3-C6 cycloalkoxy;

[0057] Y1 and Y2 are each independently selected from C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkyl, phenyl, 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, 5-7 membered aliphatic heterocycle C1-C6 alkyl or 5-7 membered aromatic heterocycle C1-C6 alkyl, and the hydrogen on the phenyl, aliphatic heterocycle or aromatic heterocycle may be substituted by one or more of the following substituents, and the substituents are selected from nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkyl or C3-C6 cycloalkoxy;

[0058] X3 is selected from hydrogen, cyano, nitro, halogen, C1-C3 alkylsulfonyl, C1-C3 alkyl or C1-C3 haloalkyl;

[0059] Q is selected from Q1, Q2, Q3 or Q4 groups;

[0060] [[ID=ll]]

[0061] R1 and R2 are each independently selected from hydrogen, methyl or ethyl;

[0062] R3 and R are each independently selected from hydrogen, chlorine or methyl;

[0063] Z is selected from Z1, Z2, Z3, Z4, Z5 or Z6 groups.

[0064]

[0065] In the definition of the compound of general formula I given above, the definitions of the terms used are as follows:

[0066] Alkyl refers to straight-chain or branched-chain forms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, n-hexyl and other groups. Cycloalkyl refers to groups including cyclic-chain forms, such as cyclopropyl, methylcyclopropyl, cyclopropylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and other groups. Alkenyl refers to straight-chain or branched-chain alkenyl groups, such as vinyl, 1-propenyl, 2-propenyl, butenyl, pentenyl and hexenyl and other groups. Alkynyl refers to straight-chain or branched-chain alkynyl groups, such as 1-propynyl, 2-propynyl, butynyl, pentynyl and hexynyl and other groups. Alkoxy refers to groups in which an alkyl group is connected to an oxygen atom at the end, such as methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy and the like. Cycloalkenyl refers to monounsaturated, diunsaturated or other polyunsaturated groups including cyclic-chain forms, such as 1-cyclopentene-1-yl, 3-cyclopentene-1-yl, 1-cyclohexene-1-yl, 3-cyclohexene-1-yl, 2,5-cyclohexadienyl and other groups. 5- to 7-membered aliphatic heterocycles containing 1 to 4 heteroatoms refer to 5- to 7-membered heterocyclic compounds without aromatic characteristics containing 1 to 4 heteroatoms, such as ethylene oxide, tetrahydrofuran, imidazolinone, caprolactam, 1,3-dioxane ring, 1,4-dioxane ring and the like. 5- to 7-membered aromatic heterocycles containing 1 to 4 heteroatoms refer to 5- to 7-membered heterocyclic compounds with aromatic characteristics containing 1 to 4 heteroatoms, such as furan, thiophene, pyrazole, pyridine and the like.

[0067] The general formula compound I of the present invention can be prepared by the following methods:

[0068] Method 1:

[0069]

[0070] The target compound I is prepared by reacting the compound of general formula II with the compound of general formula III in a suitable solvent at a temperature of -10°C to the boiling point of the suitable solvent for 0.5 to 48 hours.

[0071] The suitable solvent is selected from dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride, hexane, benzene, toluene, ethyl acetate, acetonitrile, acetic acid, tetrahydrofuran, dioxane, N,N-dimethylformamide or dimethyl sulfoxide and the like.

[0072] Adding a suitable basic substance to the reaction system is beneficial to the reaction. The suitable base is selected from organic bases such as triethylamine, N,N-dimethylaniline or pyridine and the like, or inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, potassium carbonate, sodium methoxide, sodium tert-butoxide or potassium tert-butoxide and the like.

[0073] The compound of general formula III can be prepared from the corresponding commercially available acid, and the method can refer to WO2009123714.

[0074] Method 2:

[0075]

[0076] The target compound I is prepared by reacting the compound of general formula IV with the compound of general formula V in a suitable solvent at a temperature ranging from -10°C to the boiling point of the suitable solvent for 0.5 - 48 hours.

[0077] The suitable solvent is selected from dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride, hexane, benzene, toluene, ethyl acetate, acetonitrile, acetic acid, tetrahydrofuran, dioxane, N,N-dimethylformamide or dimethyl sulfoxide, etc.

[0078] Adding a suitable basic substance to the reaction system is beneficial to the reaction. The suitable base is selected from organic bases such as triethylamine, N,N-dimethylaniline or pyridine, etc., or inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, potassium carbonate, sodium methoxide, sodium tert-butoxide or potassium tert-butoxide, etc.

[0079] The compound of general formula V can be prepared from the corresponding commercially available acid, and the method can refer to WO2009123714.

[0080] The preparation method of the compound of general formula II is as follows:

[0081]

[0082] The compound of general formula VI (commercially available) and the compound of general formula VII (commercially available) react with a suitable activator in a suitable base and solvent at a temperature ranging from -10°C to the boiling point of the suitable solvent for 0.5 - 48 hours to obtain the compound of general formula II; the suitable solvent is selected from petroleum ether, hexane, benzene, toluene, chlorobenzene, ethyl acetate, acetonitrile, tetrahydrofuran, N,N-dimethylformamide, dimethyl sulfoxide, pyridine, 2-methylpyridine, 3-methylpyridine or 4-methylpyridine, etc. The suitable activator is selected from phosgene, triphosgene, CDI, DCC, thionyl chloride, oxalyl chloride, phosphorus oxychloride or phosphorus pentachloride, etc. The suitable base is selected from N-methylimidazole or DMAP, etc.

[0083] The preparation method of the compound of general formula IV can refer to the preparation method of general formula II.

[0084] The compound of general formula I of the present invention can be used for controlling various weeds in agriculture. <l

[0085] The present invention also includes a herbicidal composition with the compound of general formula I as the active ingredient. The weight percentage content of the active ingredient in this herbicidal composition is 1 - 99%. The herbicidal composition also includes an agriculturally acceptable carrier.

[0086] The herbicidal composition of the present invention can be applied in the form of various preparations. Usually, the compounds of the present invention are dissolved or dispersed in a carrier to prepare a preparation for easier dispersion when used as a herbicide. For example, these chemical preparations can be made into wettable powders or emulsifiable concentrates, etc. Therefore, in these compositions, at least one liquid or solid carrier is added, and usually an appropriate surfactant needs to be added.

[0087] The present invention also provides an implementation method for controlling weeds, which includes applying an herbicidally effective amount of the herbicidal composition of the present invention to the surface of the weeds or the place where the weeds grow or their growth medium. A more suitable effective dose is 1 gram to 1000 grams per hectare, and the preferred effective dose is 10 grams to 500 grams per hectare. For certain applications, one or more other herbicides can be added to the herbicidal composition of the present invention, which can produce additional advantages and effects.

[0088] The compounds of the present invention can be used alone or in combination with other known insecticides, fungicides, plant growth regulators or fertilizers, etc.

[0089] It should be clear that various transformations and modifications can be made within the scope defined by the claims of the present invention.

[0090] Advantages of the present invention:

[0091] Compared with the known benzamide compounds, the general formula compounds of the present invention contain a benzoyl group and a cycloalkenoyl group substitution, with a novel structure. Moreover, the amide compounds of the present invention have unexpectedly high herbicidal activity, and also have high herbicidal activity at lower doses. They are not only highly efficient, but also reduce the usage amount of pesticides, lower the cost, and reduce environmental pollution. Detailed implementation methods

[0092] The following examples and bioassay test results can be used to further illustrate the present invention, but do not mean to limit the present invention.

[0093] Synthesis examples

[0094] Example 1. Synthesis of Compound 1-103:

[0095] (1) Synthesis of N-(1-methyl-tetrazol-5-yl)-2-chloro-3-methoxymethyl-4-methylsulfonylbenzamide

[0096]

[0097] Add 2-chloro-3-methoxymethyl-4-methylsulfonylbenzoic acid (5.0 g, 17.9 mmol), 1-methyl-5-aminotetrazole (2.1 g, 21.5 mmol), 3-methylpyridine (30 mL), and N-methylimidazole (3.0 g, 35.9 mmol) into the reaction flask. Stir at room temperature for half an hour, cool it in an ice-water bath to below 10 °C, slowly drop in thionyl chloride (3.4 g, 28.7 mmol), stir at room temperature for 2 hours, heat up to 50 °C and keep the reaction for 2 hours, cool it in an ice-water bath to below 10 °C, slowly drop in cold water, and a solid precipitates. Filter, wash the filter cake twice with 30 mL of water, and dry to obtain 3.29 g of off-white solid with a yield of 51%.

[0098] (2) Synthesis of 1-cyclohexene-1-carbonyl chloride

[0099]

[0100] Add 1-cyclohexene-1-carboxylic acid (8.5 g, 67.5 mmol), dichloromethane (300 mL), and DMF (3 drops) into the reaction flask. Slowly add oxalyl chloride (42.8 g, 337.5 mmol). Stir the mixture at room temperature for 2 hours, evaporate the solvent under reduced pressure. Then add toluene (150 mL) to the residue, stir for 3 minutes, and evaporate the solvent under reduced pressure to obtain 9.7 g of pale yellow solid, which is directly used for the next step.

[0101] (3) Synthesis of compound 1-103

[0102]

[0103] Add N-(1-methyl-tetrazol-5-yl)-2-chloro-3-methoxymethyl-4-methylsulfonylbenzamide (0.5 g, 1.4 mmol), dichloromethane (20 mL), and triethylamine (0.3 g, 2.8 mmol) into the reaction flask. Dropwise add the dichloromethane solution of the prepared 1-cyclohexene-1-carbonyl chloride (0.4 g of 1-cyclohexene-1-carbonyl chloride dissolved in 15 mL of dichloromethane). Stir at room temperature for 40 minutes, evaporate the solvent under reduced pressure. Add ethyl acetate (50 mL) and water (50 mL) to the residue for liquid-liquid extraction. Wash the organic phase with saturated brine (50 mL), dry with anhydrous magnesium sulfate, evaporate the solvent under reduced pressure, and separate the residue by column chromatography to obtain 0.4 g of pale yellow solid with a purity of 95% and a yield of 67%.

[0104] Example 2: Synthesis of compound 1-265

[0105] (1) Synthesis of N-(1-methyl-tetrazol-5-yl)-2-methylsulfonyl-4-trifluoromethylbenzamide

[0106]

[0107] Add 2-(methylsulfonyl)-4-(trifluoromethyl)benzoic acid (19.1 g, 71.2 mmol), 1-methyl-5-aminotetrazole (8.5 g, 85.4 mmol), 3-methylpyridine (100 mL), and N-methylimidazole (11.7 g, 142.0 mmol) into the reaction flask. Stir at room temperature for half an hour, cool to below 10 °C in an ice-water bath, slowly add thionyl chloride (13.6 g, 114.0 mmol) dropwise, stir at room temperature for 2 hours, heat to 50 °C and keep the reaction for 2 hours, cool to below 10 °C in an ice-water bath, slowly add cold water dropwise. Solids will precipitate. Filter, wash the filter cake twice with 100 mL of water, and dry to obtain 17.5 g of a white solid-like product with a yield of 70%.

[0108] (2) Synthesis of Compound 1-265

[0109]

[0110] Add N-(1-methyltetrazol-5-yl)-2-(methylsulfonyl)-4-(trifluoromethyl)benzamide (1.2 g, 3.4 mmol), dichloromethane (20 mL), and triethylamine (0.7 g, 6.8 mmol) into the reaction flask. Dropwise add the dichloromethane solution of the prepared 1-cyclohexene-1-carbonyl chloride (1.0 g of 1-cyclohexene-1-carbonyl chloride, 6.8 mmol dissolved in 15 mL of dichloromethane). Stir at room temperature for 40 minutes, evaporate the solvent under reduced pressure. Add ethyl acetate (50 mL) and water (50 mL) to the residue for liquid-liquid extraction. Wash the organic phase with saturated brine (50 mL), dry with anhydrous magnesium sulfate, evaporate the solvent under reduced pressure, and separate the residue by column chromatography to obtain 1.3 g of a white solid-like product with a purity of 94% and a yield of 86%.

[0111] Other compounds shown in General Formula I can be obtained by replacing the starting materials according to the method described above. For some compounds of General Formula I, refer to Table 1 and Table 2; among them, in Table 1, W is selected from CX2; in Table 2, W is selected from N.

[0112] Compound of General Formula I, where W is CX2.

[0113]

[0114] Structures and physical properties of some compounds of General Formula I in Table 1

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129] Compounds of general formula I, wherein W is N.

[0130]

[0131] Structures and physical properties of some compounds of general formula I in Table 2

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145] The 1 1H NMR data of some compounds are as follows:

[0146] Compound 1-97 (600 MHz, CDCl3): δ 8.13 (d, 1H), 7.55 (d, 1H), 6.74 (s, 1H), 4.06 (s, 3H), 3.15 (s, 3H), 2.81 (s, 3H), 2.11 - 2.12 (m, 2H), 2.01 - 2.02 (m, 2H), 1.46 - 1.48 (m, 4H).

[0147] Compound 1-103 (600 MHz, CDCl3): δ 8.18 (d, 1H), 7.68 (d, 1H), 6.75 (s, 1H), 5.08 (s, 2H), 4.06 (s, 3H), 3.51 (s, 3H), 3.26 (s, 3H), 2.11 - 2.12 (m, 2H), 1.99 - 2.00 (m, 2H), 1.44 - 1.46 (m, 4H).

[0148] Compound 1-235 (600 MHz, DMSO-d6): δ 8.09 (d, 1H), 7.93 (d, 1H), 6.82 - 6.80 (m, 1H), 4.95 (s, 2H), 4.45 (s, 3H), 3.40 (s, 3H), 3.36 (s, 3H), 2.10 - 2.06 (m, 2H), 1.92 - 1.86 (m, 2H), 1.36 - 1.28 (m, 4H).

[0149] Compound 1-237 (600 MHz, DMSO-d6): δ 8.07 (d, 1H), 7.94 (d, 1H), 6.66 - 6.63 (m, 1H), 4.95 (s, 2H), 4.44 (s, 3H), 3.40 (s, 3H), 3.36 (s, 3H), 2.40 - 2.36 (m, 2H), 2.25 - 2.21 (m, 2H), 1.72 - 1.67 (m, 2H).

[0150] Compound 1-265 (600 MHz, DMSO-d6): δ 8.38 (s, 1H), 8.32 (d, 1H), 8.27 (d, 1H), 6.72 (s, 1H), 4.15 (s, 3H), 3.40 (s, 3H), 1.92 - 1.99 (m, 4H), 1.31 - 1.35 (m, 4H).

[0151] Compound 1-266 (600 MHz, DMSO-d6): δ 8.38 (s, 1H), 8.29 (d, 1H), 8.25 (d, 1H), 6.48 (s, 1H), 4.16 (s, 3H), 3.38 (s, 3H), 2.33 - 2.35 (m, 2H), 2.13 - 2.21 (m, 2H), 1.69 - 1.74 (m, 2H).

[0152] Compound 1-267 (600 MHz, CDCl3): δ 8.16 (d, 1H), 7.76 (dd, 1H), 7.56 (d, 1H), 6.45 (t, 1H), 4.18 (s, 3H), 1.99 - 2.02 (m, 4H), 1.47 - 1.50 (m, 2H), 1.41 - 1.44 (m, 2H).

[0153] Compound 1-268 (600 MHz, CDCl3): δ 7.48 (d, 1H), 7.43 (d, 1H), 7.36 (dd, 1H), 6.73 (t, 1H), 3.98 (s, 3H), 2.09 - 2.10 (m, 2H), 2.01 - 2.02 (m, 2H), 1.43 - 1.47 (m, 4H).

[0154] Compound 1-269 (600 MHz, CDCl3): δ 8.02 (s, 1H), 7.97 (d, 1H), 7.77 (d, 1H), 6.73 (s, 1H), 4.05 (s, 3H), 3.12 (s, 3H), 2.12 - 2.13 (m, 2H), 2.03 - 2.04 (m, 2H), 1.49 - 1.50 (m, 4H).[[ID=X]] [[ID=Y]]

[0155] Compound 1-270 (600 MHz, CDCl3): δ 8.14 (d, 1H), 7.63 (d, 1H), 6.71 (t, 1H), 5.13 (s, 2H), 4.02 (s, 3H), 3.75 (t, 2H), 3.53 (t, 2H), 3.30 (s, 3H), 3.27 (s, 3H), 2.06 - 2.07 (m, 2H), 1.94 - 1.96 (m, 2H), 1.39 - 1.40 (m, 4H).

[0156] Compound 1-271 (600 MHz, CDCl3): δ 8.27 (d, 1H), 8.24 (dd, 1H), 7.74 (d, 1H), 6.70 (t, 1H), 4.03 (s, 3H), 2.11 - 2.12 (m, 2H), 2.01 - 2.02 (m, 2H), 1.45 - 1.51 (m, 4H).

[0157] Biological assay examples

[0158] Example 3: Determination of Herbicidal Activity

[0159] Seeds of broad-leaved weeds (Zinnia elegans, Abutilon theophrasti) or gramineous weeds (Setaria viridis, Echinochloa crusgalli) were sown separately in paper cups with a diameter of 7 cm filled with nutrient soil. After sowing, the seeds were covered with 1 cm of soil, compacted, and watered. Then, they were cultivated in a greenhouse according to the conventional method. After the weeds grew to the 2-3 leaf stage, foliar spraying treatment was carried out.

[0160] The original drug was dissolved in acetone, and then the test solution with the required concentration was prepared by standing in tap water with 1‰ Tween 80 according to the test requirements. According to the test design dose, spraying treatment was carried out on a crawler crop sprayer (designed and produced by Engineer Research Ltd., UK) (spraying pressure 1.95 kg / cm 2 , liquid spraying volume 500 L / hm 2 , crawler speed 1.48 km / h). The test was set with 3 replicates. After the test materials were treated, they were placed in the operation hall. After the liquid medicine dried naturally, they were placed in the greenhouse and managed according to the conventional method. The reaction of the weeds to the medicine was observed and recorded. After treatment, the control effect of the test medicine on the weeds was visually measured regularly, which was expressed by 0-100%, with "0" representing no control effect and "100%" representing complete killing.

[0161] The test results showed that the compounds of general formula I generally had a high control effect on various weeds. Among some of the tested compounds, such as compounds 1-97, 1-103, 1-265, 1-266, 1-267, 1-268, 1-269, 1-270, at the application dose of 600 g a.i. / hm 2 they had a good control effect on Zinnia elegans, Abutilon theophrasti, Setaria viridis or Echinochloa crusgalli, and the control effect was greater than or equal to 90%.

[0162] According to the above test method, some compounds of general formula I were selected to conduct an activity test for controlling Zinnia elegans with KC, and the results are shown in Table 3.

[0163] Table 3: Activity of Some Compounds of General Formula I and Control Compound KC in Controlling Zinnia elegans (post-seeding, control effect %)

[0164]

[0165]

[0166] " / " in the table indicates not tested.

[0167] According to the above test method, some compounds of general formula I were selected to conduct an activity test for controlling Abutilon theophrasti with KC, and the results are shown in Table 4.

[0168] Table 4: Activity of Some Compounds of General Formula I and Control Compound KC in Controlling Abutilon theophrasti (post-seeding, control effect %)

[0169]

[0170] In the table, " / " indicates not tested.

[0171] According to the above test method, some compounds of general formula I were selected to conduct an activity test for controlling Setaria viridis with KC, and the results are shown in Table 5.

[0172] Table 5: Activity of some compounds of general formula I and control compound KC for controlling Setaria viridis (post-seeding, control efficacy %)

[0173]

[0174] In the table, " / " indicates not tested.

[0175] According to the above test method, some compounds of general formula I were selected to conduct an activity test for controlling Echinochloa crusgalli with KC, and the results are shown in Table 6.

[0176] Table 6: Activity of some compounds of general formula I and control compound KC for controlling Echinochloa crusgalli (post-seeding, control efficacy %)

[0177]

[0178]

[0179] In the table, " / " indicates not tested.

[0180] In summary, the cycloalkene amide compounds of the present invention have excellent herbicidal activity, and also have high herbicidal activity at a relatively low dosage, and can be used for controlling various weeds in agriculture.

Claims

1. A cycloolefinamide compound, characterized in that: The compound is shown in the general formula I: Where: X1 is selected from nitro, halogen or C1-C6 alkylsulfonyl; W is selected from CX2; X2 is selected from Y1oxy C1-C6 alkyl; Y1 is selected from C1-C6 alkyl or C1-C6 alkoxy C1-C6 alkyl; X3 is selected from halogen, C1-C6 alkylsulfonyl or C1-C6 haloalkyl; Q is selected from the group Q1; R1 is selected from C1-C6 alkyl; Z is selected from C3-C8 cycloalkenyl.

2. The compound according to claim 1, characterized in that In the general formula I: X1 is selected from nitro, halogen, C1-C3 alkylsulfonyl; W is selected from CX2; X2 is selected from Y1oxy C1-C3 alkyl; Y1 is selected from C1-C6 alkyl or C1-C6 alkoxy C1-C6 alkyl; X3 is selected from halogen, C1-C3 alkylsulfonyl or C1-C3 haloalkyl; Q is selected from the group Q1; R1 is selected from methyl; Z is selected from Z1 or Z5 groups; 。 3. Use of the compound of general formula I according to claim 1, characterized in that: Use of the compound of general formula I in controlling weeds.

4. A herbicidal composition, characterized in that: The herbicidal composition comprises an active substance and an agriculturally acceptable carrier, wherein the active component is the compound of general formula I according to claim 1; and the weight percentage of the active component in the composition is 1-99%.

5. A method for controlling weeds using the herbicidal composition according to claim 4, characterized in that: Applying a herbicidally effective amount of the herbicidal composition according to claim 4 to weeds or a growth medium or site of weeds.

Images