Oxabicycloalkane compound, method for producing the same, herbicidal composition and use thereof

Abstract

The present invention belongs to the technical field of agrochemicals, and in particular relates to an oxabicycloalkane compound, a method for preparing the same, a herbicidal composition and its use. The compound is represented by the general formula I: [Formula 1] JPEG2025537252000048.jpg51137 [wherein A and B each independently represent an alkyl group, and X, Y, and Z each independently represent hydrogen, a nitro group, a halogen, or the like.] This compound has better safety to crops while maintaining equivalent or better herbicidal activity, and therefore can achieve better selectivity to crops.

Description

[Technical Field]

[0001] The present invention belongs to the technical field of agrochemicals, and in particular relates to an oxabicycloalkane compound, a method for producing the same, a herbicidal composition and its use. [Background technology]

[0002] Weed control is one of the most important factors in achieving high-efficiency agriculture. Various herbicides are available on the market. For example, patent CN1045786A discloses the effectiveness of oxabicycloalkane compound herbicides in suppressing the growth of harmful plants in rice paddies. However, the herbicidal properties and crop selectivity of these known compounds against harmful plants are not necessarily sufficient. Furthermore, due to the continued expansion of the market, issues such as weed resistance, the effective period and economic efficiency of herbicides, and growing public concern about the environment, scientists are constantly required to research and develop new, efficient, safe, and economical herbicides with different mechanisms of action. Summary of the Invention

[0003] In order to solve the above problems in the prior art, the present invention provides an oxabicycloalkane compound and its preparation method, a herbicidal composition and its use.The compound of the present invention has better safety to crops and can establish better selectivity to crops while maintaining the same or better herbicidal activity.

[0004] The technical scheme adopted in the present invention is as follows: Oxabicycloalkane compounds have the general formula I: [ka] [In the formula, A and B each independently represent alkyl; X, Y, and Z are each independently hydrogen, nitro, halogen, cyano, formyl, thiocyanato, sulfhydryl, OR 1 , C.O.R.1 , COOR 1 ,OCOR 1 , OCOOR 1 , N.R. 3 SO2R 2 , OSO2R 2 , S(O) m R 2 , N.R. 3 COR 1 , N.R. 3 COOR 1 , C(O)NR 3 OR 1 , SO2OR 1 , C(O)NR 4 R 5 , N.R. 3 C(O)NR 4 R 5 , OC(O)NR 4 R 5 , SO2NR 4 R 5 , C(S)R 1 , C(S)OR 1 , C(S)SR 2 , C(O)SR 2 , SC(O)R 1 , SC(S)R 1 ,OC(S)R 1 , -alkyl-C(S)R 1 , -Alkyl-C(S)OR 1 , -alkyl-C(O)SR 1 , -Alkyl-C(S)SR 1 , -alkyl-SC(O)R 1 , -alkyl-OC(S)R 1 , -Alkyl-SC(S)R 1 , -O-alkyl-NR 4 R 5 , -S-alkyl-NR 4 R 5 , -alkyl-O-alkyl-NR 4 R 5 , -alkyl-S-alkyl-NR 4 R 5 , -Alkyl-(C=S) n -NR 4 R 5 , -NH-alkyl-NR 4 R 5, -alkyl-OR 1 , -alkyl-COR 1 , -Alkyl-CO2R 1 , -Alkyl-OCOR 1 , -alkyl-NR 3 COR 1 , -Alkyl-SO2OR 1 , -alkyl-NR 3 SO2R 2 , -Alkyl-OSO2R 2 , -alkyl-S(O) m R 2 , -alkyl-CONR 4 R 5 , -Alkyl-SO2NR 4 R 5 , N.R. 4 R 5 , [ka] P(O)(OR 6 )2, CH2P(O)(OR 6 )2, -alkyl-CN, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl, or arylalkyl; wherein said alkyl, alkenyl, or alkynyl is each independently unsubstituted or substituted with halogen; and wherein said cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl, or arylalkyl is each independently unsubstituted or substituted with oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, -OR 10 , -SR 10 , -(CO)OR 10 , -(SO2)R 10 , -N(R 10 )2 or -O-alkyl-(CO)OR 10or two adjacent carbon atoms on the ring form a fused ring with -OCH2CH2- or -OCH2O-, which is unsubstituted or substituted with a halogen; R 1 , R 3 , R 4 and R 5 each independently represent hydrogen, aryl, arylalkyl, heterocyclyl, heterocyclylalkyl, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkoxyalkyl, or cycloalkylalkyl; the latter ten groups are selected from the group consisting of cyano, halogen, nitro, cyanothio, OR 7 , S(O) m R 9 , N.R. 7 R 8 , N.R. 8 OR 7 , C.O.R. 7 ,OCOR 7 , SCOR 7 , N.R. 8 COR 7 , CO2R 7 , COSR 7 ,CONR 7 R 8 and alkoxyalkoxycarbonyl; R 2 is aryl, arylalkyl, heterocyclyl, heterocyclylalkyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl; the latter five groups are cyano, halogen, nitro, cyanothio, OR 7 , S(O) m R 9 , N.R. 7 R 8 , N.R. 8 OR 7 , C.O.R. 7 ,OCOR 7 , SCOR 7 , N.R. 8 COR 7 , CO2R 7 , COSR 7 ,CONR7 R 8 and alkoxyalkoxycarbonyl; R 6 is methyl or ethyl; R 7 and R 8 each independently represents hydrogen, alkyl, alkenyl, or alkynyl; R 9 is alkyl, alkenyl, or alkynyl; R 10 independently represent hydrogen, alkyl, haloalkyl, phenyl, or phenyl substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy, or haloalkoxy; m represents 0, 1 or 2; n represents 0 or 1; and s represents 0, 1, 2, 3, 4 or 5.]

[0005] In one embodiment, A and B each independently represent C1-C8 alkyl; X, Y, and Z are each independently hydrogen, nitro, halogen, cyano, formyl, cyanothio, sulfhydryl, OR 1 , C.O.R. 1 , COOR 1 ,OCOR 1 , OCOOR 1 , N.R. 3 SO2R 2 , OSO2R 2 , S(O) m R 2 , N.R. 3 COR 1 , N.R. 3 COOR 1 , C(O)NR 3 OR 1 , SO2OR 1 , C(O)NR 4 R 5 , N.R. 3 C(O)NR 4 R 5 , OC(O)NR 4 R5 , SO2NR 4 R 5 , C(S)R 1 , C(S)OR 1 , C(S)SR 2 , C(O)SR 2 , SC(O)R 1 , SC(S)R 1 ,OC(S)R 1 , -(C1-C8 alkyl)-C(S)R 1 , -(C1-C8 alkyl)-C(S)OR 1 , -(C1-C8 alkyl)-C(O)SR 1 , -(C1-C8 alkyl)-C(S)SR 1 , -(C1-C8 alkyl)-SC(O)R 1 , -(C1-C8 alkyl)-OC(S)R 1 , -(C1-C8 alkyl)-SC(S)R 1 , -O-(C1-C8 alkyl)-NR 4 R 5 , -S-(C1-C8 alkyl)-NR 4 R 5 , -(C1-C8 alkyl)-O-(C1-C8 alkyl)-NR 4 R 5 , -(C1-C8 alkyl)-S-(C1-C8 alkyl)-NR 4 R 5 , -(C1-C8 alkyl)-(C=S) n -NR 4 R 5 , -NH-(C1-C8 alkyl)-NR 4 R 5 , -(C1-C8 alkyl)-OR 1 , -(C1-C8 alkyl)-COR 1 , -(C1-C8 alkyl)-CO2R 1 , -(C1-C8 alkyl)-OCOR 1 , -(C1-C8 alkyl)-NR 3 COR 1 , -(C1-C8 alkyl)-SO2OR 1 , -(C1-C8 alkyl)-NR 3 SO2R 2 , -(C1-C8 alkyl)-OSO2R 2, -(C1-C8 alkyl)-S(O) m R 2 , -(C1-C8 alkyl)-CONR 4 R 5 , -(C1-C8 alkyl)-SO2NR 4 R 5 , N.R. 4 R 5 , [ka] P(O)(OR 6 )2, CH2P(O)(OR 6 )2, -(C1-C8 alkyl)-CN, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenylC1-C8 alkyl, heterocyclyl, heterocyclylC1-C8 alkyl, aryl, or arylC1-C8 alkyl; wherein said C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl is each independently unsubstituted or substituted with halogen; and said C3-C8 cycloalkyl, C3-C8 cyclo -C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenylC1-C8 alkyl, heterocyclyl, heterocyclylC1-C8 alkyl, aryl or arylC1-C8 alkyl are each independently unsubstituted or substituted with oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, haloC1-C8 alkyl, haloC2-C8 alkenyl, haloC2-C8 alkynyl, haloC3-C8 cycloalkyl, C3-C8 cycloalkyl, -OR 10 , -SR 10 , -(CO)OR 10 , -(SO2)R 10 , -N(R 10 )2 or -O-(C1-C8 alkyl)-(CO)OR 10or two adjacent carbon atoms on the ring form a fused ring with -OCH2CH2- or -OCH2O-, which are unsubstituted or substituted with halogen; R 1 , R 3 , R 4 and R 5 each independently represent hydrogen, aryl, arylC1-C8 alkyl, heterocyclyl, heterocyclylC1-C8 alkyl, C1-C8 alkyl, haloC1-C8 alkyl, C2-C8 alkenyl, haloC2-C8 alkenyl, C2-C8 alkynyl, haloC2-C8 alkynyl, C3-C8 cycloalkyl, haloC3-C8 cycloalkyl, C1-C8 alkoxyC1-C8 alkyl, C3-C8 cycloalkylC1-C8 alkyl; the latter ten groups are selected from the group consisting of cyano, halogen, nitro, cyanothio, OR 7 , S(O) m R 9 , N.R. 7 R 8 , N.R. 8 OR 7 , C.O.R. 7 ,OCOR 7 , SCOR 7 , N.R. 8 COR 7 , CO2R 7 , COSR 7 ,CONR 7 R 8 and C1-C8 alkoxyC1-C8 alkoxycarbonyl; R 2 is aryl, arylC1-C8 alkyl, heterocyclyl, heterocyclylC1-C8 alkyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl; the latter five groups are cyano, halogen, nitro, cyanothio, OR 7 , S(O) m R 9 , N.R. 7 R 8 , N.R. 8 OR 7 , C.O.R. 7,OCOR 7 , SCOR 7 , N.R. 8 COR 7 , CO2R 7 , COSR 7 ,CONR 7 R 8 and C1-C8 alkoxyC1-C8 alkoxycarbonyl; R 6 is methyl or ethyl; R 7 and R 8 each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl; R 9 is C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl; R 10 independently represent hydrogen, C1-C8 alkyl, haloC1-C8 alkyl, phenyl, or phenyl substituted with at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, haloC1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy, or haloC1-C8 alkoxy; m represents 0, 1 or 2; n represents 0 or 1; s represents 0, 1, 2, 3, 4 or 5.

[0006] In other particular embodiments, A and B each independently represent C1-C6 alkyl; preferably, A represents methyl or ethyl; B represents methyl, ethyl, or isopropyl; X, Y, and Z are each independently hydrogen, nitro, halogen, cyano, formyl, thiocyanato, sulfhydryl, OR 1 , C.O.R. 1 , COOR 1 ,OCOR 1 , OCOOR 1 , N.R. 3 SO2R 2 , OSO2R 2 , S(O) m R2 , N.R. 3 COR 1 , N.R. 3 COOR 1 , C(O)NR 3 OR 1 , SO2OR 1 , C(O)NR 4 R 5 , N.R. 3 C(O)NR 4 R 5 , OC(O)NR 4 R 5 , SO2NR 4 R 5 , C(S)R 1 , C(S)OR 1 , C(S)SR 2 , C(O)SR 2 , SC(O)R 1 , SC(S)R 1 ,OC(S)R 1 , -(C1-C6 alkyl)-C(S)R 1 , -(C1-C6 alkyl)-C(S)OR 1 , -(C1-C6 alkyl)-C(O)SR 1 , -(C1-C6 alkyl)-C(S)SR 1 , -(C1-C6 alkyl)-SC(O)R 1 , -(C1-C6 alkyl)-OC(S)R 1 , -(C1-C6 alkyl)-SC(S)R 1 , -O-(C1-C6 alkyl)-NR 4 R 5 , -S-(C1-C6 alkyl)-NR 4 R 5 , -(C1-C6 alkyl)-O-(C1-C6 alkyl)-NR 4 R 5 , -(C1-C6 alkyl)-S-(C1-C6 alkyl)-NR 4 R 5 , -(C1-C6 alkyl)-(C=S) n -NR 4 R 5 , -NH-(C1-C6 alkyl)-NR 4 R 5 , -(C1-C6 alkyl)-OR 1, -(C1-C6 alkyl)-COR 1 , -(C1-C6 alkyl)-CO2R 1 , -(C1-C6 alkyl)-OCOR 1 , -(C1-C6 alkyl)-NR 3 COR 1 , -(C1-C6 alkyl)-SO2OR 1 , -(C1-C6 alkyl)-NR 3 SO2R 2 , -(C1-C6 alkyl)-OSO2R 2 , -(C1-C6 alkyl)-S(O) m R 2 , -(C1-C6 alkyl)-CONR 4 R 5 , -(C1-C6 alkyl)-SO2NR 4 R 5 , N.R. 4 R 5 , [ka] P(O)(OR 6 )2, CH2P(O)(OR 6)2, -(C1-C6 alkyl)-CN, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C6 alkyl, heterocyclyl, heterocyclylC1-C6 alkyl, aryl, or arylC1-C6 alkyl; said C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl are each independently unsubstituted or substituted with halogen; said C3-C6 cycloalkyl, C3-C6 cyclo -C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C6 alkyl, heterocyclyl, heterocyclylC1-C6 alkyl, aryl, or arylC1-C6 alkyl are each independently unsubstituted or C3-C6 cycloalkyl substituted with oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, haloC1-C6 alkyl, haloC2-C6 alkenyl, haloC2-C6 alkynyl, haloC3-C6 cycloalkyl, C3-C6 cycloalkyl, -OR 10 , -SR 10 , -(CO)OR 10 , -(SO2)R 10 , -N(R 10 )2 or -O-(C1-C6 alkyl)-(CO)OR 10 or two adjacent carbon atoms on the ring form a fused ring with -OCH2CH2- or -OCH2O-, which are unsubstituted or substituted with halogen; R 1 , R 3 , R 4 and R 5each independently represent hydrogen, aryl, arylC1-C6 alkyl, heterocyclyl, heterocyclylC1-C6 alkyl, C1-C6 alkyl, haloC1-C6 alkyl, C2-C6 alkenyl, haloC2-C6 alkenyl, C2-C6 alkynyl, haloC2-C6 alkynyl, C3-C6 cycloalkyl, haloC3-C6 cycloalkyl, C1-C6 alkoxyC1-C6 alkyl, C3-C6 cycloalkylC1-C6 alkyl; the latter ten groups are selected from the group consisting of cyano, halogen, nitro, cyanothio, OR 7 , S(O) m R 9 , N.R. 7 R 8 , N.R. 8 OR 7 , C.O.R. 7 ,OCOR 7 , SCOR 7 , N.R. 8 COR 7 , CO2R 7 , COSR 7 ,CONR 7 R 8 and C1-C6 alkoxyC1-C6 alkoxycarbonyl; R 2 is aryl, arylC1-C6 alkyl, heterocyclyl, heterocyclylC1-C6 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl; the latter five groups are cyano, halogen, nitro, cyanothio, OR 7 , S(O) m R 9 , N.R. 7 R 8 , N.R. 8 OR 7 , C.O.R. 7 ,OCOR 7 , SCOR 7 , N.R. 8 COR 7 , CO2R 7 , COSR 7 ,CONR 7 R 8and C1-C6 alkoxyC1-C6 alkoxycarbonyl; R 6 is methyl or ethyl; R 7 and R 8 each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl; R 9 is C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl; R 10 independently represent hydrogen, C1-C6 alkyl, haloC1-C6 alkyl, phenyl, or phenyl substituted with at least one group selected from halogen, cyano, nitro, C1-C6 alkyl, haloC1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy, or haloC1-C6 alkoxy; m represents 0, 1 or 2; n represents 0 or 1; s represents 0, 1, 2, 3, 4 or 5.

[0007] In the definition of the compounds represented by the general formula above and all structural formulas below, the technical terms used, whether used alone or in compounds, represent the following substituents: Alkyl groups having more than two carbon atoms may be linear or branched. For example, the compound "-alkyl-C(S)R 1" may be -CH2-, -CH2CH2-, -CH(CH3)-, -C(CH3)2-, and the like. Examples of alkyl groups include C1 alkyl: methyl; C2 alkyl: ethyl; C3 alkyl: propyl, such as n-propyl or isopropyl; C4 alkyl: butyl, such as n-butyl, isobutyl, tert-butyl, or 2-butyl; C5 alkyl: pentyl, such as n-pentyl; and C6 alkyl: hexyl, such as n-hexyl, isohexyl, and 1,3-dimethylbutyl. Similarly, examples of alkenyl groups include vinyl, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl, and 1-methylbut-2-en-1-yl. Examples of alkynyl include ethynyl, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, and 1-methylbut-3-yn-1-yl. Multiple bonds may be located at any position in each unsaturated group. Cycloalkyl groups are saturated carbocyclic groups having 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl. Similarly, cycloalkenyl groups are monocyclic alkenyl groups having 3 to 6 carbon ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl, with double bonds located at any position. Halogen is fluorine, chlorine, bromine, or iodine.

[0008] Unless otherwise specified, "aryl" in the present invention includes, but is not limited to, phenyl, naphthyl, [ka] "Heterocyclyl" includes, but is not limited to, saturated or unsaturated non-aromatic cyclic groups. [ka] and further includes, but is not limited to, heteroaryl, which is an aromatic cyclic group having, for example, 3 to 6 ring atoms and an optionally fused benzo ring. The 1 to 4 (e.g., 1, 2, 3, or 4) heteroatoms of the ring atoms are selected from oxygen, nitrogen, and sulfur, for example, [ka] is.

[0009] When a group is substituted with a group, it should be understood that the group is substituted with one or more identical or different groups selected from the above-mentioned groups. Furthermore, the identical or different substituents contained in the same or different substituents are independently selected and may be the same or different. This also applies to ring systems formed by different atoms and units. Furthermore, compounds that are chemically unstable under standard conditions known to those skilled in the art are excluded from the scope of the claims.

[0010] Unless otherwise specified, the term "substituted with at least one group" used herein means, for example, substituted with 1, 2, 3, 4, or 5 groups; groups without a specified linking site (including heterocyclyl, aryl, etc.) may be linked at any site, including the site bonded to C or N; when substituted, the substituent may also be substituted at any site as long as it complies with the valence bond theory. For example, a heteroaryl substituted with one methyl may be linked at any site, including the site bonded to C or N. [ka] teeth, [ka] It can be expressed as:

[0011] Depending on the nature of the substituents and their bonding modes, the compounds of general formula I and their derivatives may exist as stereoisomers. Stereoisomers can be obtained from the mixtures formed during production by conventional separation methods, such as chromatographic separation. Stereoisomers can also be selectively prepared by utilizing stereoselective reactions and optically active starting materials and / or auxiliaries. The present invention further relates to all stereoisomers encompassed by general formula I but not specifically defined, and mixtures thereof.

[0012] According to the present invention, there is provided a method for producing an oxabicycloalkane compound, comprising the steps of: A process for producing a compound of general formula I by subjecting a compound of general formula II and a compound of general formula III to a substitution reaction, the reaction being represented by the following chemical reaction scheme: [ka] [In the formula, Hal represents halogen, and the other substituents A, B, X, Y and Z are defined as above.] Preferably, the reaction is carried out in the presence of NaH or anhydrous carbonate (e.g., potassium salt, sodium salt) and a solvent; more preferably, the solvent is selected from at least one of DMF, dimethylacetamide, THF, acetonitrile, dichloroethane, DMSO, dioxane, dichloromethane, or ethyl acetate.

[0013] The compounds of the present invention can be produced by referring to the related methods described in CN1045786A and the like.

[0014] The present invention also provides a herbicidal composition comprising (i) a herbicidally effective amount of at least one oxabicycloalkane compound; optionally, the herbicidal composition further comprises (ii) a herbicidally effective amount of one or more additional herbicides and / or safeners; and preferably, the herbicidal composition further comprises (iii) an agrochemically acceptable formulation adjuvant.

[0015] The present invention also provides a method for controlling harmful plants, which comprises applying a herbicidally effective amount of at least one oxabicycloalkane compound or herbicide composition to a plant, its cultivation area, or the soil or water, thereby controlling the emergence or growth of the harmful plants.

[0016] Preferably, harmful plants include herbicide-resistant or herbicide-tolerant weed species.

[0017] According to the present invention there is also provided the use of at least one oxabicycloalkane compound or herbicidal composition for controlling harmful plants.

[0018] Preferably, the oxabicycloalkane compounds are used to control weeds in useful crops.

[0019] More preferably, the useful crops include genetically modified crops or crops treated with genome editing technology, and the weeds include herbicide-resistant or herbicide-tolerant weed species.

[0020] The compounds of formula I of the present invention have excellent herbicidal activity against a wide range of economically important monocotyledonous and dicotyledonous harmful plants.The active substances of the present invention are also effective against perennial weeds that grow from root stocks, rhizomes or other perennial organs and are difficult to control.In this respect, it is generally not important whether these substances are applied before sowing, before emergence or after emergence.Representative examples of monocotyledonous and dicotyledonous weeds that can be controlled by the compounds of the present invention can be specifically mentioned without being limited to specific species. Examples of weed species on which the active substances act effectively include the annual Avena, Lolium, Alopecurus, Phalaris, Echinochloa, Digitaria, Setaria and Cyperus, as well as the perennial Agropyron, Cynodon, Imperata and Sorghum, and monocotyledonous plants such as the perennial Cyperus.

[0021] In the case of dicotyledonous weed species, the spectrum of action extends to the annuals Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Sida, Matricaria and Abutilon, as well as the perennial weeds Convolvulus, Cirsium, Rumex and Artemisia. Under the specific conditions of rice growth, the active substances of the present invention also exhibit excellent control effects against harmful plants such as Echinochloa, Sagittaria, Alisma, Eleocharis, Scirpus, and Cyperus. When the compounds of the present invention are applied to the soil surface before emergence, weed seedlings are completely inhibited from emerging or their growth stops when they reach the cotyledon stage, and they completely die after 3 to 4 weeks. In particular, the compounds of the present invention exhibit excellent activity against Apera spica venti, Matsumurela chinense, Fallopia convolvulus, Stellaria media, Veronica hederifolia, Veronica persica, Viola tricolor, Amaranthus, Galium, and Kochia.

[0022] The compounds of the present invention have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, but cause no or only slight damage to economically important crops such as peanuts, wheat, barley, rye, rice, corn, sugar beets, cotton, and soybeans. In particular, they are highly compatible with cereals such as wheat, barley, and corn, especially wheat. For these reasons, the compounds of the present invention are highly suitable for selectively controlling the growth of harmful plants in agricultural or ornamental cultivation.

[0023] These active substances have herbicidal properties and can therefore be used to control harmful plants in the cultivation of known or to-be-introduced genetically modified plants. Genetically modified plants usually have advantageous traits, such as resistance to specific insecticides, especially specific herbicides; resistance to plant diseases, or to specific insects or pathogenic microorganisms of plant diseases, including fungi, bacteria, or viruses. Other specific traits relate to the following product characteristics, such as quantity, quality, storability, composition, and special components. Thus, the resulting genetically modified plant products are known to have increased starch content, altered starch quality, or different fatty acid compositions.

[0024] The compound of formula I of the present invention or its salt is preferably used in the cultivation of economically important genetically modified crops and ornamental plants, such as cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn, or sugar beet, cotton, soybean, rapeseed, potato, tomato, pea and other vegetable plants.The compound of formula I is preferably used as a herbicide in the cultivation of useful plants that are resistant to the toxic effects of herbicides or have been genetically modified to have resistance.

[0025] Conventional methods for breeding plants with altered traits compared to known plants include, for example, conventional breeding and mutant breeding. In other words, novel plants with improved traits can be produced by using genetic engineering techniques (see, for example, EP-0221044A, EP-0131624A). For example, several methods have been described: - methods for modifying crop plants using genetic engineering to modify starch synthesis in plants (e.g. WO92 / 11376, WO92 / 14827, WO91 / 19806); - genetically modified crop plants that are resistant to certain herbicides, such as glufosinate-P herbicides (for example, EP-0242236A, EP-0242246A), or glyphosate herbicides (WO92 / 00377), or sulfonylurea herbicides (EP-0257993A, US-5013659A); - genetically modified crops, such as cotton, capable of producing Bacillus thuringiensis toxins (Bt toxins) that confer resistance to certain plant-infesting pests (EP-0142924A, EP-0193259A); - Genetically modified crop plants with modified fatty acid composition (WO91 / 13972).

[0026] Numerous molecular biological techniques are known that allow the creation of genetically modified plants with modified traits (e.g., Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2 nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker, “Gene und Klone” [Genes and Clones], VCH Weinheim, 2 nd(See, for example, "Trends in Plant Science", vol. 1, 1996, pp. 423-431). For genetic engineering, nucleic acid molecules can be introduced into plasmids to allow mutations or sequence changes to occur by recombination of DNA sequences. Using standard methods, such as those described above, base substitutions, deletion of subsequences, or addition of natural or synthetic sequences can be performed. Adapters or linkers can be added to DNA fragments to link them together.

[0027] Plant cells with gene products with reduced activity can be produced by the methods described below, for example, by expressing at least one suitable antisense RNA and one sense RNA to achieve a co-suppression effect, or by expressing at least one appropriately constructed ribozyme that specifically cleaves the transcript of the above-mentioned gene product.

[0028] For this purpose, both DNA molecules containing the entire coding sequence of the gene product, including any flanking sequences that may be present, and DNA molecules containing only a portion of the coding sequence long enough to elicit an antisense effect in cells can be used. Sequences that are highly identical to the coding sequence of the gene product, but not completely identical, can also be used.

[0029] When nucleic acid molecule is expressed in plant, the protein synthesized can be localized in any compartment of plant cell.However, to achieve localization in specific compartment, for example, coding region can be linked with DNA sequence that causes localization in specific compartment.Such sequences are known to those skilled in the art (for example, see Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).

[0030] Transgenic plant cells can be modified in whole plants using known techniques. Transgenic plants can be of any plant species, for example, monocotyledonous and dicotyledonous plants. In this way, transgenic plants can be obtained whose traits are modified by overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences, or by expression of heterologous (= foreign) genes or gene sequences.

[0031] When the active substance of the present invention is used in genetically modified crops, in addition to the inhibitory effect on harmful plants that can be observed in other crops, it often produces special effects on corresponding genetically modified crops, such as widening or improving the spectrum of weeds that can be controlled, changing the application rate, favorably combining the drug resistance of genetically modified crops with the performance of herbicides, and even having an effect on the growth and yield of genetically modified crops.Therefore, the present invention also provides the use of compound as herbicide for controlling harmful plants in genetically modified crops.

[0032] Furthermore, the compounds of the present invention can significantly control the growth of crop plants. These compounds can be used to target and control plant components, for example, by inducing drought or growth inhibition or regulating plant metabolism, and thereby promote harvesting. Furthermore, these compounds are also suitable for controlling and inhibiting the growth of harmful plants without damaging the growth of crop plants. Plant growth inhibition plays an important role in many monocotyledonous and dicotyledonous crops, as it can reduce or completely prevent lodging.

[0033] The compounds of the present invention can be applied in conventional formulations such as wettable powders, emulsifiable concentrates, spray solutions, dusts, or granules. Therefore, the present invention also provides herbicidal compositions containing the compounds of formula I. The compounds of formula I can be formulated in various ways depending on general biological and / or chemical physical parameters. Examples of suitable formulations include wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water emulsions and water-in-oil emulsions, spray solutions, suspension concentrates (SC), oil dispersions (OD), oil- or aqueous dispersions, oil-miscible solutions, dusting powders (DP), capsule suspensions (CS), seed dressing compositions, granules for dusting and soil application, spray granules, coated granules, and adsorbed granules, water-dispersible granules (WG), water-soluble granules (SG), ultra-low-voltage formulations, microcapsules, and waxes. These individual formulation types are known and are described, for example, in Winnacker-Kuchler, "Chemische Technologie" [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4 th Edition, 1986;Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker, NY, 1973;K. Martens, “Spray Drying” Handbook, 3 rd Ed. 1979, G. Goodwin Ltd. London.

[0034] The necessary formulation aids, such as inert substances, surfactants, solvents and other additives, are likewise known and are described, for example, in Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2 nd Ed., Dorland Books, Caldwell NJ;H. v. Olphen, “An Introduction to Clay Colloid Chemistry”, 2 ndEd., J. Wiley & Sons, NY; C. Marsden, “Solvents Guide”, 2 nd Ed., Interscience, NY 1963; “McCutcheon's Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridgewood NJ; Sisley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., NY, 1964; [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4 th Edition, 1986.

[0035] Wettable powders contain, in addition to the active substance, diluents or inert substances, ionic and / or nonionic surfactants (wetting agents, dispersants), such as polyethoxylated alkylphenols, polyethoxylated fatty alcohols, polyethoxylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylphenylsulfonates, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate, or sodium methyloleoyl taurate, and are uniformly dispersible in water. To prepare wettable powders, the herbicidal active substance is finely ground using conventional equipment such as a hammer mill, fan mill, or air jet mill, and mixed with formulation adjuvants simultaneously or sequentially.

[0036] Emulsifiable concentrate is prepared by dissolving active substance in organic solvent, such as butanol, cyclohexanone, dimethylformamide, xylene or aromatic compounds with relatively high boiling points, or hydrocarbons, or the mixture of these solvents, and adding one or more ionic and / or nonionic surfactants (emulsifiers).The emulsifiers that can be used include calcium alkylarylsulfonates, such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensates, alkyl polyethers, sorbitan esters, such as sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, such as polyoxyethylene sorbitan fatty acid esters.

[0037] Dusts are obtained by grinding the active substance with finely divided solid substances, such as natural clays such as talc, kaolin, bentonite and pyrophyllite, or diatomaceous earth. Aqueous or oily suspension concentrates can be prepared, for example, by wet grinding in a commercial bead mill, as described below, with or without the addition of surfactants as mentioned above for other formulation types.

[0038] Emulsions such as oil-in-water (EW) emulsions can be prepared using aqueous organic solvents with a stirrer, colloid mill and / or static mixer, and, if necessary, surfactants as described above for other formulation types can be added.

[0039] Granules can be prepared either by spraying the active substance onto an adsorbent and granulating it together with the inert substance, or by concentrating the active substance on the surface of a carrier such as sand or kaolinite and granulating the inert substance with an adhesive binder such as polyvinyl alcohol, sodium polyacrylate, or mineral oil. Suitable active substances can be granulated by methods conventionally used to prepare fertilizer granules, and fertilizer can be mixed in, if necessary. Water-dispersible granules are usually prepared by conventional methods such as spray drying, fluidized bed granulation, disk granulation, mixing using a high-speed mixer, and extrusion molding without the use of solid inert substances.

[0040] Regarding the methods for preparing granules by the disk method, the fluidized bed method, the extruder method and the spray method, see, for example, the following "Spray-Drying Handbook" 3 rd ed. 1979, G. Goodwin Ltd., London;JE Browning, “Agglomeration”, Chemical and Engineering, 1967, pages 147 ff.;“Perry's Chemical Engineer's Handbook”, 5 th Ed., McGraw-Hill, New York 1973, pp. 8-57. For details on formulating crop protection products, see, for example, G.C. Klingman, "Weed Control as a Science," John Wiley and Sons Inc., New York, 1961, pages 81-96 and J.D. Freyer, S.A. Evans, "Weed Control Handbook," 5 th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

[0041] Agrochemical formulations generally contain 0.1 to 99% by weight, particularly 0.1 to 95% by weight, of the active substance of formula I. In wettable powders, the active substance concentration is, for example, about 10 to 99% by weight, with the remainder consisting of conventional formulation ingredients. In emulsifiable concentrates, the active substance concentration can be about 1 to 90% by weight, preferably 5 to 80% by weight. Powders typically contain 1 to 30% by weight, preferably 5 to 20% by weight, of the active substance, while sprays contain about 0.05 to 80% by weight, preferably 2 to 50% by weight. In the case of water-dispersible granules, the active substance content is primarily determined by whether the active substance is liquid or solid, and further by the auxiliary agents, fillers, etc. used during granulation. In the case of water-dispersible granules, the active substance content is, for example, 1 to 95% by weight, preferably 10 to 80% by weight.

[0042] Furthermore, the active substance formulation may contain tackifiers, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents, solvents, fillers, carriers, colorants, antifoaming agents, evaporation inhibitors, as well as pH adjusters and viscosity adjusters, which are normally customary in all cases.

[0043] Based on these formulations, mixtures can also be prepared in the form of premixes or tank mixes with other pesticidal active substances, such as insecticides, acaricides, herbicides and fungicides, as well as safeners, fertilizers and / or plant growth regulators.

[0044] Suitable active substances that can be mixed with the compound of formula I of the present invention in mixed formulations or tank-mix formulations are known substances, for example, as described in "World Herbicide New Product Technology Handbook, China Agricultural Science and Farming Techniques Press, September 2010" and the documents cited therein. For example, the active substances of the following herbicides can be mixed with compound 1 (Note: Compounds are named by "common names" according to the International Organization for Standardization (ISO), or by chemical names with code numbers, where appropriate):

[0045] (1) HPPD (hydroxyphenylpyruvate dioxygenase) inhibitors: including, but not limited to, the following types: 1) Triketones, such as sulcotrione (CAS number: 99105-77-8); mesotrione (CAS number: 104206-82-8); bicyclopyrone (CAS number: 352010-68-5); tembotrione (CAS number: 335104-84-2); tefuryltrione (CAS number: 473278-76-1); and benzobicyclone (CAS number: 156963-66-5); 2) Diketonitriles, such as 2-cyano-3-cyclopropyl-1-(2-methylsulfonyl-4-trifluoromethylphenyl)-propane-1,3-dione (CAS number: 143701-75-1); 2-cyano-3-cyclopropyl-1-(2-methylsulfonyl-3,4-dichlorophenyl)-propane-1,3-dione (CAS number: 212829-55-5) and 2-cyano-1-[4-(methylsulfonyl)-2-trifluoromethylphenyl]-3-(1-methylcyclopropyl)propane-1,3-dione (CAS number: 143659-52-3); 3) Isoxazoles, such as isoxaflutole (CAS number: 141112-29-0); isoxachlorthole (CAS number: 141112-06-3); and clomazone (CAS number: 81777-89-1); 4) Pyrazoles, such as topramezone (CAS number: 210631-68-8); pyrasulfotole (CAS number: 365400-11-9); pyrazoxifene (CAS number: 71561-11-0); pyrazolate (CAS number: 58011-68-0); benzofenap (CAS number: 82692-44-2); bipyrazone (CAS number: 1622908-18-2); tolpyralate (CAS number: 1101132-67-5); fenpyrazone (CAS number: 1992017-55-6); cipirafluon (CAS number: 1855929-45-1); and tripyrasulfone (CAS number: 1911613-97-2); 5) Benzophenone; 6) Others: Lancotrione (CAS number: 1486617-21-3); Fenquinotrione (CAS number: 1342891-70-6); and Fursulfinam (CAS number: 2421252-30-2); and those described in CN105264069A.

[0046] (2) EPSPS (enolpyruvylshikimate phosphate synthase) inhibitors: for example, sulfosate, glyphosate, glyphosate-isopropylammonium, and glyphosate trimesium.

[0047] (3) PPO (protoporphyrinogen oxidase) inhibitors: They are classified into pyrimidinediones, diphenyl ethers, phenylpyrazoles, N-phenylphthalimides, thiadiazoles, oxadiazoles, triazolinones, oxazolidinediones and other herbicides with different chemical structures.

[0048] In exemplary embodiments, pyrimidinedione herbicides include, but are not limited to, butafenacil (CAS No.: 134605-64-4), saflufenacil (CAS No.: 372137-35-4), benzfendizone (CAS No.: 158755-95-4), thiafenacil (CAS No.: 1220411-29-9), [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetic acid ethyl ester (epirifenacil, CAS No.: 353292-31-6), 1-methyl-6- Trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione (CAS number: 1304113-05-0), 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione (CAS number: 212754-02-4), flupropacil (CAS number: 120890-70-2), isoxazoline-containing uracils (e.g., compounds disclosed in CN105753853A) [ka] uracil pyridines as disclosed in WO2017 / 202768 and uracils as disclosed in WO2018 / 019842; Diphenyl ether herbicides include, but are not limited to, fomesafen (CAS number: 72178-02-0), oxyfluorfen (CAS number: 42874-03-3), aclonifen (CAS number: 74070-46-5), ethoxyfen-ethyl (CAS number: 131086-42-5), lactofen (CAS number: 77501-63-4), clomethoxyfen (CAS number: 32861-85-1), chlornitrofen (CAS number: 1836-77-7), fluoroglycofen-ethyl (CAS number: 77501-90-7), acifluorfen or its sodium salt (CAS No.: 50594-66-6 or 62476-59-9), bifenox (CAS No.: 42576-02-3), ethoxyfen (CAS No.: 188634-90-4), fluoronitrofen (CAS No.: 13738-63-1), furyloxyfen (CAS No.: 80020-41-3), nitrofluorfen (CAS No.: 42874-01-1), and halosafen (CAS No.: 77227-69-1); Phenylpyrazole herbicides include, but are not limited to, pyraflufen-ethyl (CAS No.: 129630-19-9) and fluazolate (CAS No.: 174514-07-9); N-phenylphthalimide herbicides include, but are not limited to, flumioxazin (CAS No.: 103361-09-7), cinidon ethyl (CAS No.: 142891-20-1), flumipropyne (CAS No.: 84478-52-4) and flumiclorac pentyl (CAS No.: 87546-18-7); Thiadiazole herbicides include, but are not limited to, fluthiacet-methyl (CAS No.: 117337-19-6), fluthiacet (CAS No.: 149253-65-6) and thidiazimine (CAS No.: 123249-43-4); Oxadiazole herbicides include, but are not limited to, oxadiargyl (CAS No.: 39807-15-3) and oxadiazon (CAS No.: 19666-30-9); Triazolinone herbicides include, but are not limited to, carfentrazone (CAS No.: 128621-72-7), carfentrazone-ethyl (CAS No.: 128639-02-1), sulfentrazone (CAS No.: 122836-35-5), azafenidin (CAS No.: 68049-83-2) and bencarbazone (CAS No.: 173980-17-1); Oxazolidinedione herbicides include pentoxazone (CAS number: 110956-75-7); Other herbicides include, but are not limited to, pyraclonil (CAS number: 158353-15-2), flufenpyr-ethyl (CAS number: 188489-07-8), profluazole (CAS number: 190314-43-3), trifludimoxadine (CAS number: 1258836-72-4), N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS number: 452098-92-9), N-tetrahydrofurfuryl-3-(2 ,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS number: 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS number: 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS number: 452100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo[1,3,5]triazinane-2,4-dione (CAS number: 451484-50-7), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydroisoindole-1,3-dione (CAS number: 1300118-96-0), methyl (E)-4-[2-chloro-5-[4-chloro-5-(difluoromethoxy)-1H-methylpyrazol-3-yl]-4-fluorophenoxy]-3-methoxy-but-2-enoate (CAS number: 948893-00-3), phenylpyridines disclosed in WO2016 / 120116, benzoxazinone derivatives disclosed in EP09163242.2, and carboxylic acid derivative-substituted iminoaryl compounds disclosed in CN113105405A.

[0049] (4) ALS (acetolactate synthase) inhibitors include, but are not limited to, the following herbicides or mixtures thereof: Sulfonylureas, such as amidosulfuron, azimsulfuron, bensulfuron, bensulfuron methyl, chlorimuron, chlorimuron ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron methyl sodium, foramsulfuron, halosulfuron, halosulfuron methyl, imazosulfuron, iodosulfuron, iodosulfuron methyl sodium, iofensulfuron, iofensulfuron sodium, mesosulfuron Furoin, metazosulfuron, metsulfuron, metsulfuron methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazosulfuron ethyl, rimsulfuron, sulfometuron, sulfometuron methyl, sulfosulfuron, thifensulfuron, thifensulfuron methyl, triasulfuron, tribenuron, tribenuron methyl, trifloxysulfuron, trifloxysulfuron sodium, triflusulfuron, triflusulfuron methyl and tritosulfuron; Imidazolinones, such as imazamethabenz, imazamethabenzmethyl, imazamox, imazapic, imazapyr, imazaquin and imazethapyr; Triazolopyrimidine herbicides and sulfanilides, such as cloransulam, cloransulam-methyl, diclosulam, flumetsulam, florasulam, metosulam, penoxsulam, pyroxsulam, pyrimisulfan and triafamone; Pyrimidinylbenzoic acids, such as bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]benzoic acid 1-methylethyl ester (CAS number: 420138-41-6), 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]benzoic acid propyl ester (CAS number: 420138-40-5) and N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS number: 420138-01-8); Sulfonylaminocarbonyl-triazolinone herbicides, for example, flucarbazone, flucarbazone sodium, propoxycarbazone, propoxycarbazone sodium, thiencarbazone, and thiencarbazone methyl.

[0050] (5) ACCase (acetyl-CoA carboxylase) inhibitors: for example, fentiaprop, alloxydim, alloxydim sodium, butroxydim, clethodim, clodinafop, clodinafop propargyl, cycloxydim, cyhalofop, cyhalofop butyl, diclofop, diclofop methyl, fenoxaprop, fenoxaprop ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop butyl, fluazifop-P, fluazifop- P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim, 4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2, 6,6-tetramethyl-2H-pyran-3(6H)-one (CAS number: 1312337-72-6); 4-(2',4'-dichloro-4-cyclopropyl[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS number: 1312337-45-3); 4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one ( CAS number: 1033757-93-5; 4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS number: 1312340-84-3); 5-(acetyloxy)-4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS number: 1312337-48-6);5-(Acetyloxy)-4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one; 5-(Acetyloxy)-4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS no. No.: 1312340-82-1; 5-(acetyloxy)-4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS No.: 1033760-55-2); 4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one Tetramethyl-5-oxo-2H-pyran-3-ylmethyl carbonate (CAS number: 1312337-51-1); 4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylmethyl carbonate; 4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl) 4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylmethyl carbonate (CAS number: 1312340-83-2); and 4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylmethyl carbonate (CAS number: 1033760-58-5).

[0051] (6) GS (glutamine synthetase) inhibitors: for example, bialaphos / viranaphos, viranaphos-sodium, glufosinate-ammonium, glufosinate, and glufosinate-P.

[0052] (7) PDS (phytoene desaturase) inhibitors: for example, fluorochloridone, flurtamone, beflubutamid-M, norflurazon, fluridone, diflufenican, picolinafen, 4-[3-(trifluoromethyl)phenoxy]-2-[4-(trifluoromethyl)phenyl]pyrimidine (CAS number: 180608-33-7).

[0053] (8) DHPS (dihydropteroate synthase) inhibitors: for example, asulam.

[0054] (9) DXPS (deoxy-D-xylulose phosphate synthase) inhibitors: for example, bixlozone and clomazone.

[0055] (10) HST (homogentisate solanesyltransferase) inhibitors: for example, cyclopyrimorate.

[0056] (11) SPS (solanesyl diphosphate synthase) inhibitors: for example, aclonifen.

[0057] (12) Cellulose synthesis inhibitors: for example, indaziflam, triaziflam, chlorthiamid, dichlobenil, isoxaben, flupoxam, 1-cyclohexyl-5-pentafluorophenyloxy-1 4 -[1,2,4,6]thiatriazin-3-ylamine (CAS number: 175899-01-1) and the azines disclosed in CN109688807A.

[0058] (13) VLCFAS (very long chain fatty acid synthesis) inhibitors: including but not limited to the following types: 1) Chloroacetamides, such as acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor, S-metolachlor, petoxamide, pretilachlor, propachlor, propisochlor and thenylchlor; 2) α-oxyacetamides, such as flufenacet and mefenacet; 3) α-thioacetamides, such as anilophos and piperophos; 4) Azolylcarboxamides, such as cafenstrole, fentrazamide and ipfencarbazone; 5) benzofurans, such as benfuresate and ethofumesate; 6) Isoxazolines, such as fenoxasulfone and pyroxasulfone; 7) Ethylene oxide, for example, indanophane and tridiphane; 8) Thiocarbamates, such as cycloate, dimepiperate, S-ethyldipropyl(thiocarbamate) (EPTC), esprocarb, molinate, orbencarb, prosulfocarb, thiobencarb / benthiocarb, triallate, vernolate, isoxazolines of formulae II.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9, and other isoxazoline compounds described in patents such as WO2006 / 024820, WO2006 / 037945, WO2007 / 071900 and WO2007 / 096576; [ka]

[0059] (14) Fatty acid thioesterase inhibitors: for example, cinmethylin and methiozolin.

[0060] (15) Serine-threonine-protein phosphatase inhibitors: for example, endothal.

[0061] (16) Lycopene cyclase inhibitors: for example, amitrole.

[0062] (17) Microtubule formation inhibitors: for example, benefin / benfluralin, butralin, dithiopyr, thiazopyr, ethalfluralin, prodiamine, butamifos, oryzalin, pendimethalin, chlorthaldimethyl / DCPA, [ka] Trifluralin, propyzamide / pronamide and dinitramine (CAS number: 29091-05-2).

[0063] (18) Auxin mimics: for example, 2,4,5-trichlorophenoxyacetic acid (2,4,5-T), 2,4-dichlorophenoxyacetic acid (2,4-D), 2,4-dichlorophenoxybutyric acid (2,4-DB), 3,4-dichlorophenoxybutyric acid (3,4-DB), 2,4-DEB (CAS number: 94-83-7), 4-chlorophenoxyacetic acid (4-CPA), 4-CPP (CAS number: 3307-39-9), cloprop (CAS number: 101-10-0), and clofop (CAS number: 26 129-32-8), clomeprop, dichlorprop, (4-chloro-2-methylphenoxy)acetic acid (MCPA), 2-methyl-4-chlorophenoxybutyric acid (MCPB), mecoprop, aminopyralid, clopyralid, aminocyclopyrachlor, florpyrauxifen benzyl, halaxifene, quinclorac, benazolin ethyl, picloram, 4-amino-3,5,6-trichloropicolinic acid, chloramben, quinmerac, fluroxypyr, triclopyr, and dicamba.

[0064] (19) D1 serine 264 binders (and other non-histidine 215 binders): for example, ametryn, atrazine, cyanazine, dimethametryn, prometon, prometryn, propazine, simazine, terbuthylazine, terbutryn, chlorotoluron, diuron, fluometuron, isoproturon, linuron, metobromuron, methabenzthiazuron (CAS number: 18691-97-9), monuron, tebuthiuron, hexazinone, metamitron, Metribuzin, bromacil, lenacil, terbacil, chloridazon / pyrazone, amicarbazone, desmedipham, phenmedipham, chloranocryl / dicryl (CAS number: 2164-09-2), propanil, chlorazine (CAS number: 580-48-3), ciprazine (CAS number: 22936-86-3), trietadine (CAS number: 1912-26-1), metoprothrin (CAS number: 841-06-5), and simetryn.

[0065] (20) D1 histidine 215 binding agents: for example, bromoxynil, ioxynil, pyridate and bentazone.

[0066] (21) Auxin transport inhibitors: for example, diflufenzopyr (CAS number: 109293-97-2) and naptalam.

[0067] (22) PS1 electron converters: e.g., diquat and paraquat.

[0068] (23) Microtubule structure inhibitors: for example, carbetamide (CAS number: 16118-49-3), barban (CAS number: 101-27-9), and chlorpropham.

[0069] (24) Separating agents: for example, dinoseb and 4,6-dinitro-o-cresol (DNOC).

[0070] (25) Others: for example, bensulide, bromobutide, cumyluron, difenzoquat, pyributicarb (CAS No.: 88678-67-5), disodium methyl arsenate (DSMA), sodium monomethyl arsenate (MSMA), dymron / daimuron, etobenzanide, flamprop-m, fosamine, oxaziclomefone, pelargonic acid, diphenamide, naproanilide, napropamide, napropamide-m, benzofluor (CAS No.: 68672-17-3), camphendichlor (CAS No.: 56141-00-5), dipropalin (CAS No.: 1918-08-7), etonipromide (CAS No. : 76120-02-0), bromobornyl (CAS number: 25671-46-9), monisouron (CAS number: 55807-46-0), bromofenoxim (CAS number: 13181-17-4), clasifos (CAS number: 215655-76-8), chloradifop (CAS number: 60074-25-1), quicaoxy, brompyrazone (CAS number: 304284-0), etiodin, methiuron (CAS number: 21540-35-2), metoxuron (CAS number: 19937-59-8), tetrafluron (CAS number: 27954-37-6), thidiazuron (CAS number: 51707-55-2), acrolein and funaihekaoring.

[0071] In one particular embodiment, Compound 1 [ka] The other herbicide (ingredient B) to be mixed with is selected from one or more of the following compounds: bensulfuron methyl (CAS number: 83055-99-6), pyrazosulfuron ethyl (CAS number: 93697-74-6), penoxsulam (CAS number: 219714-96-2), thifensulfuron methyl (CAS number: 79277-27-3), flumetsulam (CAS number: 98967-40-9), [ka] Oxadiazon (CAS number: 19666-30-9), oxadiargyl (CAS number: 39807-15-3), oxyfluorfen (CAS number: 42874-03-3), pyraclonil (CAS number: 158353-15-2), flumioxazin (CAS number: 103361-09-7), propanil (CAS number: 709-98-8), bentazone (C AS number: 25057-89-0), isoproturon (CAS number: 34123-59-6), chlorotoluron (CAS number: 15545-48-9), metribuzin (CAS number: 21087-64-9), atrazine (CAS number: 1912-24-9), terbuthylazine (CAS number: 5915-41-3), prometryne (CAS number: 7287-19-6), [ka] Florpyrauxifen benzyl (CAS number: 1390661-72-9), fluroxypyr (CAS number: 69377-81-7), MCPA-isooctyl (CAS number: 26544-20-7), 2,4-D-isooctyl (CAS number: 25168-26-7), [ka] Tripyrasulfone (CAS number: 1911613-97-2), [ka] Bipyrazone (CAS number: 1622908-18-2), fenpyrazone (CAS number: 1992017-55-6), mesotrione (CAS number: 104206-82-8), benzobicyclon (CAS number: 156963-66-5), tefuryltrione (CAS number: 473278-76-1), isoxaflutole (CAS number: 141112-29-0), acetochlor (CAS number: 34256-82-1), pretilachlor (CAS number: 51218-49-6), butachlor (CAS number: 23184-66- 9), mefenacet (CAS number: 73250-68-7), fentrazamide (CAS number: 158237-07-1), anilofos (CAS number: 64249-01-0), pyroxasulfone (CAS number: 447399-55-5), triallate (CAS number: 2303-17-5), pendimethalin (CAS number: 40487-42-1), butralin (CAS number: 33629-47-9), diflufenican (CAS number: 83164-33-4), beflubutamid-M (CAS number: 113614-09-8), [ka] Clomazone (CAS number: 81777-89-1), bixolozone (CAS number: 81777-95-9), oxaziclomefone (CAS number: 153197-14-9), cyhalofop-butyl (CAS number: 122008-85-9), metamifop (CAS number: 256412-89-2) and profoxydim (CAS number: 139001-49-3).

[0072] Generally, when the herbicide compounds described herein that can be used in the present invention can form geometric isomers, e.g., E / Z isomers, both the pure isomers and mixtures thereof can be used in the compositions of the present invention. When the herbicide compounds described herein have one or more chiral centers (compounds of formula I), [ka] has at least three chiral centers C1 * , C2 *and C4 * ), and therefore, when present as enantiomers or diastereomers, either the pure enantiomers, diastereomers, or mixtures thereof can be used in the compositions of the present invention. When the herbicidal compounds described herein have ionizable functional groups, they can also be used in the form of agrochemically acceptable salts. Generally, salts of their cations and acid addition salts of their acids are suitable, provided that the cations and anions, respectively, do not adversely affect the activity of the active compounds. Preferred cations are alkali metal ions, preferably lithium, sodium, and potassium; alkaline earth metal ions, preferably calcium and magnesium; and transition metal ions, preferably manganese, copper, zinc, and iron; and also ammonium, and cations having one to four hydrogen atoms at C1-C2. 4- Alkyl, Hydroxy-C1-C 4- Alkyl, C1-C 4- Alkoxy-C1-C 4- Alkyl, Hydroxy-C1-C 4- Alkoxy-C1-C 4- Substituted ammonium ions substituted with alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium (olamine salt), 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium (diglycolamine salt), di(2-hydroxyeth-1-yl)ammonium (diolamine salt), tris(2-hydroxyethyl)ammonium (trolamine salt), tris(2-hydroxypropyl)ammonium, benzyltrimethylammonium, benzyltriethylammonium, N,N,N-trimethylethanolammonium (choline salt); further, tri(C1-C2) ions such as phosphonium ions, sulfonium ions, preferably trimethylsulfonium ions.4- alkyl) sulfonium, sulfoxonium ions, preferably tri(C-C 4- (alkyl)sulfoxonium, and finally polyamines such as N,N-bis-(3-aminopropyl)methylamine and diethylenetriamine. The usable anions of the acid addition salts are primarily chloride, bromide, fluoride, iodide, bisulfate, methylsulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and C1-C 4- Anions of alkanoic acids, preferably formate, acetate, propionate and butyrate.

[0073] The herbicidal compounds having a carboxyl group described herein can be used in the acid form, in the form of an agriculturally suitable salt as described above, or in the form of an agrochemically acceptable derivative, such as mono- and di-C-C 6- Amides such as alkylamides or arylamides include allyl esters, propargyl esters, C1-C 10- As esters such as alkyl esters, alkoxyalkyl esters, tefuryl ((tetrahydrofuran-2-yl)methyl) ester, and also C1-C 10- It can be used as a thioester, such as an alkyl thioester. Preferred are mono- and di-C1-C 6-Alkylamides are methylamides and dimethylamides. Preferred arylamides are, for example, N-anilides and 2-chloroanilides. Preferred alkyl esters are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1-methylhexyl), meptyl (1-methylheptyl), heptyl, octyl, or isooctyl (2-ethylhexyl) esters. Preferred C1-C4 alkoxy-C1-C4 alkyl esters are linear or branched C1-C4 alkoxyethyl esters, such as 2-methoxyethyl ester, 2-ethoxyethyl ester, 2-butoxyethyl (butotyl) ester, 2-butoxypropyl ester, or 3-butoxypropyl ester. Linear or branched C1-C 10 An example of an alkyl thioester is an ethyl thioester.

[0074] For use, commercially available formulations are diluted with water in the usual manner, as needed, for example, wettable powders, emulsifiable concentrates, dispersions, and water-dispersible granules. Products in the form of dusts, granules for soil application, or solutions for spraying and atomization usually do not require further dilution with inert substances before use. The required application rate of the compound of formula I varies depending on external conditions such as temperature, humidity, and the nature of the herbicide used. The application rate can vary over a wide range, for example, from 0.001 to 1.0 kg ai / ha or more of active substance, but is preferably from 0.005 to 750 g ai / ha. [Example]

[0075] The following examples are intended to illustrate, but not to limit, the invention. The scope of protection claimed by the invention is defined by the appended claims.

[0076] Considering the economical efficiency and diversity of compounds, several compounds were preferably synthesized. Among the many compounds synthesized, carefully selected compounds are shown in Table 1 below. The structures of specific compounds and information on corresponding compounds are listed in Table 1. The compounds in Table 1 are intended to better explain the present invention, but are not intended to limit the present invention. Those skilled in the art should not understand that the scope of the above-mentioned subject matter of the present invention is limited to the compounds listed below.

[0077] [Table 1] JPEG2025537252000023.jpg244159JPEG2025537252000024.jpg249156JPEG2025537252000025.jpg235157JPEG2025537252000026.jpg223156

[0078] Tables A to H show the racemic compounds (general formula I) having a chiral center in Table 1 above. [ka] C1 of the compound represented by * , C2 * and C4 * The carbon atom in is the chiral center. ) is replaced with the (1R,2R,4R) configuration, (1S,2R,4R) configuration, (1R,2S,4R) configuration, (1R,2R,4S) configuration, (1S,2S,4R) configuration, (1S,2R,4S) configuration, and (1S,2S,4S) configuration, respectively. In Table A, the items under the column heading "Number" are written in order as "1(1R,2R,4R) to 79(1R,2R,4R)," and other tables have a similar structure. For example, "1(1R,2R,4R)" corresponds to compound "1" in Table 1, and C1 * is R configuration, C2 * is R configuration, C4 * will be in R configuration.

[0079] Several methods for preparing the compounds of the present invention are detailed in the following schemes and examples. The raw materials may be commercially purchased or may be prepared by methods known in the literature or as described in the detailed description. Those skilled in the art will understand that other synthetic routes can also be used to synthesize the compounds of the present invention. While specific raw materials and conditions for the synthetic routes are described below, they can be easily replaced with other similar raw materials and conditions. Various isomers of the compounds obtained by these modifications or variations of the preparation methods of the present invention are all encompassed within the scope of the present invention. Furthermore, the preparation methods described below can be further modified using conventional chemical methods well known to those skilled in the art in accordance with the present disclosure. For example, appropriate group protection during the reaction can be included.

[0080] The methods shown below are used to further understand the manufacturing method of the present invention, and the specific materials, varieties and conditions used are intended to further illustrate the present invention and are not intended to limit the reasonable scope of the present invention. The reagents used in the synthesis of the compounds shown in the following tables are commercially available or can be easily prepared by one skilled in the art.

[0081] Representative examples of compounds are shown below. Since the synthesis methods for other compounds are similar, detailed explanations are omitted here. 1. Synthesis of Compound 1 Compound 1-2 (0.37 g, 2.2 mmol, 1.1 equiv.) and NaH (96 mg, 2.4 mmol, 1.2 equiv.) were dissolved in 20 mL of DMF and stirred at room temperature for 0.5 hours. Compound 1-1 (0.53 g, 2.0 mmol, 1 equiv.) was then added and the mixture was heated to 40 °C and reacted for 5 hours. The reaction was monitored until the starting materials were completely reacted. The reaction solution was poured into 20 mL of ice water and extracted three times with 20 mL of ethyl acetate. The organic phase was concentrated under reduced pressure and separated, and purified on a silica gel column to obtain compound 1 (0.4 g, 57% yield). [ka]

[0082] 2. Synthesis of Compound 3 Compound 3-1 (1.13 g, 4.4 mmol, 1 equiv.) was dissolved in 20 mL of DMF, and sodium hydride (0.21 g, 8.8 mmol, 2 equiv.) was added in an ice bath. The mixture was stirred at room temperature for 0.5 h. Cinmethyline intermediate 1-2 (0.8 g, 4.4 mmol, 1.1 equiv.) was added and the mixture was stirred at room temperature for 12 h. The reaction was monitored until the starting material had completely reacted. Water was added to the reaction solution, which was then extracted three times with ethyl acetate, washed three times with saturated brine, and dried over anhydrous sodium sulfate. After stirring, the sample was passed through a column, and the fraction was centrifuged and dried to obtain compound 3 (0.92 g, 54.1% yield). [ka]

[0083] 3. Synthesis of Compound 1 (1S,2R,4R) Compound 1-3 (1 equivalent) was added to 5 ml of DMF, and sodium hydride (2 equivalents) was added in an ice bath. The mixture was stirred for 0.5 hours in an ice bath. Compound 1-4 (1 equivalent) was then added to the reaction solution, and the mixture was allowed to react at room temperature overnight. After in-process control was completed, the reaction was quenched by adding water to the reaction solution, and EA was added twice for extraction. The organic phase was washed twice with saturated brine and dried over anhydrous sodium sulfate. The sample was stirred and purified by normal phase chromatography to obtain compound 1 (1S,2R,4R). [ka]

[0084] 4. Synthesis of Compound 1 (1S,2S,4R) Compound 1-5 (1 equivalent) was added to 5 ml of DMF, and sodium hydride (2 equivalents) was added in an ice bath. The mixture was stirred for 0.5 hours in an ice bath. Compound 1-4 (1 equivalent) was added to the reaction solution, and the mixture was allowed to react at room temperature overnight. After in-process control was completed, the reaction was quenched by adding water to the reaction solution, and EA was added twice for extraction. The organic phase was washed twice with saturated brine and dried over anhydrous sodium sulfate. The sample was stirred and purified by normal phase chromatography to obtain compound 1 (1S,2S,4R). [ka]

[0085] Assessment of biological activity: (1) Pre-emergence test experiment: The criteria for activity levels (i.e., growth inhibition rate) for plant damage were as follows: Level 9: Completely dead Level 8: Growth suppression rate is between 90% and 100% Level 7: Growth suppression rate is between 80% and 90% Level 6: Growth suppression rate is between 70% and 80% Level 5: Growth inhibition rate is between 50% and 70% Level 4: Growth suppression rate is between 30% and 50% Level 3: Growth suppression rate is between 20% and 30% Level 2: Growth suppression rate is between 10% and 20% Level 1: Growth suppression rate is less than 10% Level 0: No effect

[0086] The growth inhibition rate mentioned above is the live weight inhibition rate.

[0087] Monocotyledonous and dicotyledonous weed seeds, as well as major crop seeds (wheat, corn, rice, soybean, peanut, cotton, rapeseed, millet, and sorghum), were placed in soil-filled plastic pots and covered with soil to a depth of 0.5 to 2 cm. The test compounds of the present invention were each dissolved in acetone, Tween 80 added, and diluted with a certain amount of water to obtain a solution of a certain concentration. The solution was sprayed immediately after sowing. After spraying, the plants were grown in a greenhouse for four weeks, and the test results were observed. The compound doses applied were 3.75 g ai / ha, 7.5 g ai / ha, 15 g ai / ha, 30 g ai / ha, 60 g ai / ha, and 120 g ai / ha. Representative data are shown in Table 2. [Table 2]

[0088] From the above, it can be seen that the compounds of the present invention have excellent effects, have significantly higher herbicidal activity than the control compounds A and B, and have improved crop safety compared to the control compound C while maintaining high herbicidal activity, i.e., have excellent selectivity, and in particular, when the control compound C is used for sealing weeds, it does not cause unacceptable phytotoxicity to wheat.

[0089] On the other hand, tests on major weeds in wheat fields and rice paddies have shown that the compounds of the present invention generally have excellent weed control effects, and in particular, they exhibit extremely high activity against broadleaf weeds with excellent commercial value, such as Monochoria vaginalis, Cyperus difformis, Ludwigia prostrata, Lolium perenne, Alopecurus aequalis, and Beckmannia syzigachne, which are resistant to ALS inhibitors, as well as Cyperaceae.

[0090] (2) Evaluation of the safety of transplanted and directly sown rice and the effectiveness of weed control in rice paddies: After filling 1 / 1,000,000 hectare pots with rice paddy soil, seeds of Echinochloa crusgalli, Echinochloa phyllopogon, Monochoria vaginalis, Leptochloa chinensis, and Ludwigia prostrata were sown, lightly covered with soil, and placed in a greenhouse equipped with a water reservoir 0.5–1 cm deep. The next day or the day after, tubers of Sagittaria trifolia were planted. The reservoir depth was then maintained at 3–4 cm. When Echinochloa crusgalli, Echinochloa phyllopogon and Leptochloa chinensis reached the 0.5-leaf stage and Sagittaria trifolia reached the 1-leaf stage, a WP or SC aqueous dilution of the compound of the present invention, prepared according to a conventional formulation method, was uniformly added dropwise using a pipette to the plants to achieve the specified effective amount for treatment.

[0091] To simulate direct-seeded rice paddies, a container was first filled with 5 cm of water and thoroughly mixed with mud to form a slurry. Rice seeds were then sown. After the slurry became clear, the water layer was removed. The soil was kept moist and the pesticide solution was evenly sprayed with a sprayer. Three to four days after spraying, the soil was rehydrated to a depth of 3 cm.

[0092] Furthermore, 1 / 1,000,000 ha pots were filled with rice paddy soil, which was then leveled and water was maintained at a depth of 2-3 cm. The following day, three-leaf stage rice (Japonica rice) was transplanted at a transplanting depth of 2-3 cm. Three days after transplanting, the plants were treated with the compounds of the present invention in the same manner as above.

[0093] The application rates of the compounds used in the above experiments were 3.75 g ai / ha, 7.5 g ai / ha, 15 g ai / ha, 30 g ai / ha, 60 g ai / ha, and 120 g ai / ha. Weed growth was observed with the naked eye 14 days after treatment, and rice growth was observed 7 days after treatment. Efficacy was evaluated according to the activity level criteria described above. Representative data are shown in Table 3. [Table 3]

[0094] Therefore, the compounds of the present invention have superior herbicidal activity and / or rice safety compared to the control compounds A, B and C.

[0095] (3) Activity test of the composition: The required active ingredient B was purchased from a reagent company or synthesized by known methods. All technical materials were dissolved in acetone solvent and diluted with 0.1% Tween 80 emulsifier in water, and used immediately after dilution.

[0096] (A) Early postemergence treatment by foliar spray (F-EP): Weeds were grown using the pot culture method. A 180 × 140 mm plastic nutrient bowl filled with air-dried, sieved topsoil collected from the field (occupying 4 / 5 of the bowl) was placed in an enamel dish, and the initial moisture content of the soil was adjusted to 20%. Plump, uniformly sized weed seeds were selected and soaked in lukewarm water at 25°C for 6 hours. Germination was then promoted in a biochemical incubator at 28°C in the dark. Freshly germinated weed seeds were placed evenly on the soil surface and then covered with soil 0.5–1 cm thick, depending on the seed size.

[0097] Cultivation was carried out in a sun-controlled greenhouse under conditions of 20-30°C, natural light, and relative humidity of 57-72%. The soil was loamy, with an organic matter content of 1.63%, a pH of 7.1, alkaline-hydrolyzable nitrogen of 84.3 mg / kg, rapidly available phosphorus of 38.5 mg / kg, and rapidly available potassium of 82.1 mg / kg.

[0098] Each treatment was replicated four times, with four pots each containing 20 weed seeds.

[0099] In the test, the chemicals were applied a total of one time. Weeds were thinned at the 1- to 2-leaf stage, and 10 plants were maintained per treatment for later use.

[0100] The fully grown test material was placed on a 0.5 m 2 The mixture was spread evenly on a platform measuring 1000 m², and sprayed onto the leaves at a rate of 450 kg / ha and a spray pressure of 0.3 MPa using a 3WP-2000 walk-behind spray tower. After all the spray solution had been sprayed, the air valve was closed, and after 30 seconds the spray tower door was opened and the nutrient bowl was removed. The air valve was then opened, and the spray tube was washed with 50 ml of water. After treatment, the test material was moved to a greenhouse and grown as usual.

[0101] (B) Soil sealing treatment (S): Weeds were grown in a sun-controlled greenhouse at 20-30°C, with natural light and a relative humidity of 57-72%. The soil was loam with an organic matter content of 1.63%, a pH of 7.1, alkaline-hydrolyzable nitrogen of 84.3 mg / kg, rapidly available phosphorus of 38.5 mg / kg, and rapidly available potassium of 82.1 mg / kg. Pots were filled quantitatively with test soil, then irrigated from the bottom until the soil was completely saturated. Test weed seeds were allowed to germinate, and then sown uniformly and quantitatively on the soil surface, covered with 0.5-1 cm of soil depending on seed size, and ready for use 72 hours after sowing.

[0102] Each treatment was replicated four times, with four pots each containing 20 weed seeds.

[0103] The fully seeded test material was placed in a 0.5 m 2The solution was spread evenly on a platform measuring 1000 m², and sprayed onto the leaves at a rate of 450 kg / ha and a spray pressure of 0.3 MPa using a 3WP-2000 walk-behind spray tower. After all the solution had been sprayed, the air valve was closed, and after 30 seconds the spray tower door was opened and the nutrient bowl was removed. The air valve was then opened, and the spray tube was washed by spraying 50 ml of water.

[0104] (C) Data research and statistical analysis An absolute count method was used. The whole seedlings of surviving weeds were cut off along the soil surface with a blade, and the fresh weight of the weeds was measured using an analytical balance. The fresh weight of dead weeds was 0.

[0105] The survey was conducted once, 21 days after treatment.

[0106] The theoretical fresh weight suppression rate of each treatment combination was calculated using Gowing's method (E0 = X + YX * Y / 100). The type of combined effect of the two combinations on weeds was then evaluated by comparing it with the measured suppression rate (E). A synergistic effect was observed when E-E0 > 10%, an antagonistic effect when E-E0 < -10%, and an additive effect when -10% ≤ E-E0 ≤ 10%. The optimal ratio was determined based on the actual control effect, herbicide properties, and formulation balance. In the formula, X represents the fresh weight suppression rate of active ingredient A at dose P, and Y represents the fresh weight suppression rate of active ingredient B at dose Q. The statistical results are shown in Table 4.

[0107] [Table 4] JPEG2025537252000035.jpg240170JPEG2025537252000036.jpg234170JPEG2025537252000037.jpg170170

[0108] On the other hand, as a result of numerous tests, it has been found that the compounds of the present invention and many of their compositions exhibit excellent selectivity against many grasses such as turfgrass, bermudagrass, tall fescue, bluegrass, ryegrass, and seashore paspalum, and can control many important grass weeds and broadleaf weeds. In tests of different herbicide application methods, the compounds of the present invention and many of their compositions exhibit excellent selectivity and commercial value against sugarcane, sunflower, potato, fruit trees, vegetables, and the like.

Claims

1. Oxabicycloalkane compounds represented by general formula I: 【Chemistry 1】 [In the formula, A and B each independently represent alkyl; X, Y and Z each independently represent hydrogen, nitro, halogen, cyano, formyl, thiocyanato, sulfhydryl, OR １ , C.O.R. １ , COOR １ , O.C.O.R. １ , OCOOR １ , N.R. ３ SO ２ R ２ , OSO ２ R ２ , S(O) ｍ R ２ , N.R. ３ COR １ , N.R. ３ COOR １ , C(O)NR ３ OR １ , S.O. ２ OR １ , C(O)NR ４ R ５ , N.R. ３ C(O)NR ４ R ５ , OC(O)NR ４ R ５ , S.O. ２ NR ４ R ５ , C(S)R １ , C(S) OR １ , C(S)SR ２ , C(O)SR ２ , SC(O)R １ , SC(S)R １ , O.C.(S)R １ , -alkyl-C(S)R １ , -alkyl-C(S)OR １ , -alkyl-C(O)SR １ , -alkyl-C(S)SR １ , -alkyl-SC(O)R １ , -alkyl-OC(S)R １ , -alkyl-SC(S)R １ , —O-alkyl-NR ４ R ５ , —S-alkyl-NR ４ R ５ , -alkyl-O-alkyl-NR ４ R ５ , -alkyl-S-alkyl-NR ４ R ５ , -alkyl-(C=S) ｎ -NR ４ R ５ , —NH-alkyl-NR ４ R ５ , -alkyl-OR １ , -alkyl-COR １ , -alkyl-CO ２ R １ , -alkyl-OCOR １ , -alkyl-NR ３ COR １ , -alkyl-SO ２ OR １ , -alkyl-NR ３ SO ２ R ２ , -alkyl-OSO ２ R ２ , -alkyl-S(O) ｍ R ２ , -alkyl-CONR ４ R ５ , -alkyl-SO ２ NR ４ R ５ , N.R. ４ R ５ , 【Chemistry 2】 P(O)(OR ６ ) ２ , C.H. ２ P(O)(OR ６ ) ２ , -alkyl-CN, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl, or arylalkyl; wherein said alkyl, alkenyl, or alkynyl is each independently unsubstituted or substituted with halogen; wherein said cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl, or arylalkyl is each independently unsubstituted or substituted with oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, -OR １０ , -SR １０ , -(CO)OR １０ , -(SO ２ ) R １０ , -N(R １０ ) ２ or —O-alkyl-(CO)OR １０ or two adjacent carbon atoms on the ring are unsubstituted or substituted with halogen, —OCH ２ CH ２ - or -OCH ２ forming a condensed ring with O-; R １ , R ３ , R ４ and R ５ each independently represent hydrogen, aryl, arylalkyl, heterocyclyl, heterocyclylalkyl, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkoxyalkyl, cycloalkylalkyl; the latter ten groups are selected from cyano, halogen, nitro, cyanothio, OR ７ , S(O) ｍ R ９ , N.R. ７ R ８ , N.R. ８ OR ７ , C.O.R. ７ , O.C.O.R. ７ , SCOR ７ , N.R. ８ COR ７ , CO ２ R ７ , COSR ７ , C.O.R. ７ R ８ and alkoxyalkoxycarbonyl; R ２ is aryl, arylalkyl, heterocyclyl, heterocyclylalkyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl; the latter five groups are cyano, halogen, nitro, cyanothio, OR ７ , S(O) ｍ R ９ , N.R. ７ R ８ , N.R. ８ OR ７ , C.O.R. ７ , O.C.O.R. ７ , SCOR ７ , N.R. ８ COR ７ , CO ２ R ７ , COSR ７ , C.O.R. ７ R ８ and alkoxyalkoxycarbonyl; R ６ is methyl or ethyl; R ７ and R ８ each independently represents hydrogen, alkyl, alkenyl, or alkynyl; R ９ is alkyl, alkenyl, or alkynyl; R １０ independently represent hydrogen, alkyl, haloalkyl, phenyl, or phenyl substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy, or haloalkoxy; m represents 0, 1 or 2; n represents 0 or 1; and s represents 0, 1, 2, 3, 4 or 5.

2. A and B each independently represent C1-C8 alkyl; X, Y and Z are each independently hydrogen, nitro, halogen, cyano, formyl, thiocyanato, sulfhydryl, OR １ , C.O.R. １ , COOR １ , O.C.O.R. １ , OCOOR １ , N.R. ３ SO ２ R ２ , OSO ２ R ２ , S(O) ｍ R ２ , N.R. ３ COR １ , N.R. ３ COOR １ , C(O)NR ３ OR １ , S.O. ２ OR １ , C(O)NR ４ R ５ , N.R. ３ C(O)NR ４ R ５ , OC(O)NR ４ R ５ , S.O. ２ NR ４ R ５ , C(S)R １ , C(S) OR １ , C(S)SR ２ , C(O)SR ２ , SC(O)R １ , SC(S)R １ , O.C.(S)R １ , -(C1-C8 alkyl)-C(S)R １ , -(C1-C8 alkyl)-C(S)OR １ , -(C1-C8 alkyl)-C(O)SR １ , -(C1-C8 alkyl)-C(S)SR １ , -(C1-C8 alkyl)-SC(O)R １ , -(C1-C8 alkyl)-OC(S)R １ , -(C1-C8 alkyl)-SC(S)R １ , —O—(C1-C8 alkyl)-NR ４ R ５ , —S—(C1-C8 alkyl)-NR ４ R ５ , —(C1-C8 alkyl)-O—(C1-C8 alkyl)-NR ４ R ５ , -(C1-C8 alkyl)-S-(C1-C8 alkyl)-NR ４ R ５ , -(C1-C8 alkyl)-(C=S) ｎ -NR ４ R ５ , —NH—(C1-C8 alkyl)-NR ４ R ５ , -(C1-C8 alkyl)-OR １ , -(C1-C8 alkyl)-COR １ , -(C1-C8 alkyl)-CO ２ R １ , -(C1-C8 alkyl)-OCOR １ , -(C1-C8 alkyl)-NR ３ COR １ , -(C1-C8 alkyl)-SO ２ OR １ , -(C1-C8 alkyl)-NR ３ SO ２ R ２ , -(C1-C8 alkyl)-OSO ２ R ２ , -(C1-C8 alkyl)-S(O) ｍ R ２ , -(C1-C8 alkyl)-CONR ４ R ５ , -(C1-C8 alkyl)-SO ２ NR ４ R ５ , N.R. ４ R ５ , 【Transformation 3】 P(O)(OR ６ ) ２ , C.H. ２ P(O)(OR ６ ) ２ , -(C1-C8 alkyl)-CN, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenylC1-C8 alkyl, heterocyclyl, heterocyclylC1-C8 alkyl, aryl, or arylC1-C8 alkyl; wherein said C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl is each independently unsubstituted or substituted with halogen; and said C3-C8 cycloalkyl, C3-C8 cyclo alkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclyl, heterocyclyl C1-C8 alkyl, aryl, or aryl C1-C8 alkyl are each independently unsubstituted or C3-C8 cycloalkyl substituted with oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, or C1-C8 alkyl; -OR １０ , -SR １０ , -(CO)OR １０ , -(SO ２ ) R １０ , -N(R １０ ) ２ Or —O—(C1-C8 alkyl)-(CO)OR １０ or two adjacent carbon atoms on the ring are unsubstituted or substituted with halogen, —OCH ２ CH ２ - or -OCH ２ forming a condensed ring with O-; R １ , R ３ , R ４ and R ５ each independently represent hydrogen, aryl, aryl C1-C8 alkyl, heterocyclyl, heterocyclyl C1-C8 alkyl, C1-C8 alkyl, halo C1-C8 alkyl, C2-C8 alkenyl, halo C2-C8 alkenyl, C2-C8 alkynyl, halo C2-C8 alkynyl, C3-C8 cycloalkyl, halo C3-C8 cycloalkyl, C1-C8 alkoxy C1-C8 alkyl, C3-C8 cycloalkyl C1-C8 alkyl; the latter ten groups are preferably cyano, halogen, nitro, cyanothio, OR ７ , S(O) ｍ R ９ , N.R. ７ R ８ , N.R. ８ OR ７ , C.O.R. ７ , O.C.O.R. ７ , SCOR ７ , N.R. ８ COR ７ , CO ２ R ７ , COSR ７ , C.O.R. ７ R ８ and C1-C8 alkoxyC1-C8 alkoxycarbonyl; R ２ is aryl, aryl C1-C8 alkyl, heterocyclyl, heterocyclyl C1-C8 alkyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl; the latter five groups are cyano, halogen, nitro, cyanothio, OR ７ , S(O) ｍ R ９ , N.R. ７ R ８ , N.R. ８ OR ７ , C.O.R. ７ , O.C.O.R. ７ , SCOR ７ , N.R. ８ COR ７ , CO ２ R ７ , COSR ７ , C.O.R. ７ R ８ and C1-C8 alkoxyC1-C8 alkoxycarbonyl; R ６ is methyl or ethyl; R ７ and R ８ each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl; R ９ is C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl; R １０ are independently hydrogen, C1-C8 alkyl, haloC1-C8 alkyl, phenyl, or phenyl substituted with at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, haloC1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy, or haloC1-C8 alkoxy; 2. The oxabicycloalkane compound of claim 1, wherein m represents 0, 1, or 2; n represents 0 or 1; and s represents 0, 1, 2, 3, 4, or 5.

3. A and B each independently represent C1-C6 alkyl; X, Y and Z are each independently hydrogen, nitro, halogen, cyano, formyl, thiocyanato, sulfhydryl, OR １ , C.O.R. １ , COOR １ , O.C.O.R. １ , OCOOR １ , N.R. ３ SO ２ R ２ , OSO ２ R ２ , S(O) ｍ R ２ , N.R. ３ COR １ , N.R. ３ COOR １ , C(O)NR ３ OR １ , S.O. ２ OR １ , C(O)NR ４ R ５ , N.R. ３ C(O)NR ４ R ５ , OC(O)NR ４ R ５ , S.O. ２ NR ４ R ５ , C(S)R １ , C(S) OR １ , C(S)SR ２ , C(O)SR ２ , SC(O)R １ , SC(S)R １ , O.C.(S)R １ , -(C1-C6 alkyl)-C(S)R １ , -(C1-C6 alkyl)-C(S)OR １ , -(C1-C6 alkyl)-C(O)SR １ , -(C1-C6 alkyl)-C(S)SR １ , -(C1-C6 alkyl)-SC(O)R １ , -(C1-C6 alkyl)-OC(S)R １ , -(C1-C6 alkyl)-SC(S)R １ , —O—(C1-C6 alkyl)-NR ４ R ５ , —S—(C1-C6 alkyl)-NR ４ R ５ , —(C1-C6 alkyl)-O—(C1-C6 alkyl)-NR ４ R ５ , -(C1-C6 alkyl)-S-(C1-C6 alkyl)-NR ４ R ５ , -(C1-C6 alkyl)-(C=S) ｎ -NR ４ R ５ , —NH—(C1-C6 alkyl)-NR ４ R ５ , -(C1-C6 alkyl)-OR １ , -(C1-C6 alkyl)-COR １ , -(C1-C6 alkyl)-CO ２ R １ , -(C1-C6 alkyl)-OCOR １ , -(C1-C6 alkyl)-NR ３ COR １ , -(C1-C6 alkyl)-SO ２ OR １ , -(C1-C6 alkyl)-NR ３ SO ２ R ２ , -(C1-C6 alkyl)-OSO ２ R ２ , -(C1-C6 alkyl)-S(O) ｍ R ２ , -(C1-C6 alkyl)-CONR ４ R ５ , -(C1-C6 alkyl)-SO ２ NR ４ R ５ , N.R. ４ R ５ , 【Chemistry 4】 P(O)(OR ６ ) ２ , C.H. ２ P(O)(OR ６ ) ２ , -(C1-C6 alkyl)-CN, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C6 alkyl, heterocyclyl, heterocyclylC1-C6 alkyl, aryl, or arylC1-C6 alkyl; wherein said C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl is each independently unsubstituted or substituted with halogen; said C3-C6 cycloalkyl, C3-C6 cyclo alkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl, heterocyclyl C1-C6 alkyl, aryl, or aryl C1-C6 alkyl are each independently unsubstituted or C3-C6 cycloalkyl substituted with oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, or C1-C6 alkyl; -OR １０ , -SR １０ , -(CO)OR １０ , -(SO ２ ) R １０ , -N(R １０ ) ２ Or —O—(C1-C6 alkyl)-(CO)OR １０ or two adjacent carbon atoms on the ring are unsubstituted or substituted with halogen, —OCH ２ CH ２ - or -OCH ２ forming a condensed ring with O-; R １ , R ３ , R ４ and R ５ each independently represent hydrogen, aryl, aryl C1-C6 alkyl, heterocyclyl, heterocyclyl C1-C6 alkyl, C1-C6 alkyl, halo C1-C6 alkyl, C2-C6 alkenyl, halo C2-C6 alkenyl, C2-C6 alkynyl, halo C2-C6 alkynyl, C3-C6 cycloalkyl, halo C3-C6 cycloalkyl, C1-C6 alkoxy C1-C6 alkyl, C3-C6 cycloalkyl C1-C6 alkyl; the latter ten groups are cyano, halogen, nitro, cyanothio, OR ７ , S(O) ｍ R ９ , N.R. ７ R ８ , N.R. ８ OR ７ , C.O.R. ７ , O.C.O.R. ７ , SCOR ７ , N.R. ８ COR ７ , CO ２ R ７ , COSR ７ , C.O.R. ７ R ８ and C1-C6 alkoxyC1-C6 alkoxycarbonyl; R ２ is aryl, aryl C1-C6 alkyl, heterocyclyl, heterocyclyl C1-C6 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl; the latter five groups are cyano, halogen, nitro, cyanothio, OR ７ , S(O) ｍ R ９ , N.R. ７ R ８ , N.R. ８ OR ７ , C.O.R. ７ , O.C.O.R. ７ , SCOR ７ , N.R. ８ COR ７ , CO ２ R ７ , COSR ７ , C.O.R. ７ R ８ and C1-C6 alkoxyC1-C6 alkoxycarbonyl; R ６ is methyl or ethyl; R ７ and R ８ each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl; R ９ is C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl; R １０ are independently hydrogen, C1-C6 alkyl, haloC1-C6 alkyl, phenyl, or phenyl substituted with at least one group selected from halogen, cyano, nitro, C1-C6 alkyl, haloC1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy, or haloC1-C6 alkoxy; 2. The oxabicycloalkane compound of claim 1, wherein m represents 0, 1, or 2; n represents 0 or 1; and s represents 0, 1, 2, 3, 4, or 5.

4. 2. The oxabicycloalkane compound of claim 1 selected from any one of Table 1 and Tables AH.

5. A method for producing the oxabicycloalkane compound according to any one of claims 1 to 4, comprising the following steps: A process for producing a compound of general formula I by subjecting a compound of general formula II and a compound of general formula III to a substitution reaction, the process being represented by the following chemical reaction scheme: 【Transformation 5】 wherein Hal represents halogen, and the definitions of the other substituents A, B, X, Y and Z are as set forth in any one of claims 1 to 4. preferably, the reaction is carried out in the presence of NaH or anhydrous carbonate and a solvent; more preferably, the solvent is selected from at least one of DMF, dimethylacetamide, THF, acetonitrile, dichloroethane, DMSO, dioxane, dichloromethane, and ethyl acetate.

6. (i) A herbicidal composition comprising at least one oxabicycloalkane compound according to any one of claims 1 to 4 in a herbicidally effective amount.

7. (ii) further comprising one or more additional herbicides and / or safeners in a herbicidally effective amount; preferably, the additional herbicides are bensulfuron methyl, pyrazosulfuron ethyl, penoxsulam, thifensulfuron methyl, flumetsulam, 【Transformation 6】 Oxadiazon, oxadiargyl, oxyfluorfen, pyraclonil, flumioxazin, propanil, bentazon, isoproturon, chlorotoluron, metribuzin, atrazine, terbuthylazine, prometryn, 【Transformation 7】 Florpyrauxifenbenzyl, fluroxypyr, MCPA-isooctyl, 2,4-D-isooctyl, 【Transformation 8】 tripyrasulfone, 【Chemistry 9】 Bipyrazone, fenpyrazone, mesotrione, benzobicyclon, tefuryltrione, isoxaflutole, acetochlor, pretilachlor, butachlor, mefenacet, fentrazamide, anilofos, pyroxasulfone, triallate, pendimethalin, butralin, diflufenican, beflubutamide-M, 【Chemistry 10】 7. The composition of claim 6, wherein the active ingredient is selected from the group consisting of clomazone, bixolozone, oxaziclomefone, cyhalofop-butyl, metamifop, and profoxydim.

8. 8. The composition of claim 6 or 7, further comprising (iii) an agrochemically acceptable formulation adjuvant.

9. 10. A method for controlling harmful plants, comprising applying a herbicidally effective amount of at least one oxabicycloalkane compound according to any one of claims 1 to 4 or a herbicidal composition according to any one of claims 6 to 8 to plants, their cultivated land, soil or water, to control the emergence or growth of the harmful plants; preferably, the harmful plants comprise herbicide-resistant or herbicide-tolerant weed species.

10. 10. Use of at least one oxabicycloalkane compound according to any one of claims 1 to 4 or a herbicidal composition according to any one of claims 6 to 8 for controlling harmful plants; preferably, the oxabicycloalkane compound is used for controlling weeds in useful crops; more preferably, the useful crops include genetically modified crops or crops treated with genome editing technology, and the weeds include herbicide-resistant or herbicide-tolerant weed species.

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