Herbicide compounds and methods of using them

Abstract

The present invention relates to novel herbicidally active compounds, pesticidal compositions thereof, processes for their preparation and their use for controlling the growth of undesirable plants (e.g. weeds), for example in agricultural fields.

Description

[Technical Field]

[0001] The present invention relates to a novel herbicidal active compound, a pesticide composition thereof, a method for preparing the same, and its use for controlling the growth of undesirable plants (e.g., weeds) in agricultural land, for example. [Background technology]

[0002] Weeds often hinder the efficient use of land and water resources, typically competing with desirable plants for water, nutrients, light, carbon dioxide, and space. Many weeds are also aesthetically unsightly, especially when they appear within clusters of desired plants such as St. Augustine grass or Kentucky bluegrass in a homeowner's lawn. Weeds can also obstruct visibility, pose a fire hazard around buildings, and reduce the efficiency of irrigation systems. When weeds appear in waterways such as rivers and lakes, they contribute to water quality degradation, making the water unsuitable for cooking and industrial use. Furthermore, some weeds act toxicly on other plants, animals, and humans by secreting toxic substances known as allelopathic compounds or by spreading agents that can cause allergies and / or disease. Finally, weeds provide shelter for insects and rodents that spread disease or are otherwise harmful to desired plants, animals, or humans.

[0003] Weeds cause agricultural losses to crops, consistently exceeding the losses caused by other classes of agricultural pests each year. In addition to reducing crop quality, weed infestations can reduce achievable crop yields by up to 100% of theoretically achievable yields. Many approaches, including mechanical, agricultural, biological, and chemical techniques, have evolved to control weed infestations.

[0004] Mechanical means such as pulling by hand, tilling or cultivating, deep plowing, mowing, cutting, burning, and / or mulching may be attempted to eradicate or control weeds. Cover crops can also be planted to cover the ground when more valuable crops are not being cultivated, thus typically minimizing the weed infestation that would normally occur in open fields. Crop rotation and planting of “suppression” crops adapted to grow more vigorously than weeds have also been attempted as means of controlling weed infestation. In addition to these mechanical and agricultural techniques, biological methods of weed control have also been attempted, such as the introduction of predator populations that habitually feed on weeds and thereby reduce weed populations.

[0005] Mechanical, agricultural, and biological methods of weed control, while sometimes helpful in reducing weed infestations, are not entirely satisfactory. Firstly, mechanical and agricultural techniques are quite labor-intensive and require the use of limited physical and capital resources. Furthermore, environmental factors beyond the control of the farmer or homeowner, such as excessive rainfall, can reduce the effectiveness of these mechanical and agricultural techniques. Similarly, biological techniques, such as the introduction of predator populations, are not entirely satisfactory because predators may not be selective only to weed populations.

[0006] Chemically active herbicides represent another potential weed control technique. These chemical herbicides can be classified into pre-emergence herbicides and post-emergence herbicides. Pre-emergence herbicides typically prevent weed seed germination, while post-emergence herbicides kill weeds after the seeds have germinated and weed growth has begun.

[0007] Pre-emergence herbicides can be effective if they are present in the required dosage when weed seeds are ready to germinate. However, this timing issue highlights a major problem with pre-emergence herbicides. Specifically, if a pre-emergence herbicide is not applied before weed seed germination or decomposes, the weed seeds will germinate freely and begin to grow into mature weeds. In addition, pre-emergence herbicides are typically weed-specific and are not equally effective against all types of weeds. The timing problem inherent in pre-emergence herbicides can be avoided by using post-emergence herbicides, which are applied only after weed seeds have germinated and weeds have begun to grow actively. However, many post-emergence herbicides currently available are non-selective herbicides and will therefore kill desirable plants in addition to weeds.

[0008] Many pre- and post-emerging herbicides also suffer from other problems. Specifically, many pre- and post-emerging herbicides are moderately or highly toxic to humans and animals, and can have harmful effects far exceeding their intended weed control effects. Toxic herbicides can cause immediate or long-term harm to humans applying the herbicide and to humans present when the herbicide is applied. Furthermore, residual concentrations of toxic herbicides remaining in soil or water after application can pose a significant threat to humans and animals, including terrestrial animals and amphibians, as well as fish, through contact with or runoff from the treated area. In addition, public concern about the use of toxic chemicals as herbicides and the potential for their widespread and long-term effects on environmental quality demands opposition to the continued use of these toxic herbicides.

[0009] There is a need for herbicide solutions that avoid critical timing issues related to pre-emergence herbicide application. Furthermore, there is a need for herbicide solutions that avoid the toxic effects of currently available pre-emergence and post-emergence herbicides on humans, animals, and the environment in general. In addition, there is a need for economically efficient post-emergence weed control techniques that selectively control weeds without disrupting or hindering the growth of desired plants. Moreover, there is a need for compositions that reduce the amount of herbicide required to achieve sufficient weed control while minimizing harm to crop plants.

[0010] As more weeds become resistant to herbicides, alternative compositions with superior weed control are desired. Furthermore, as no-till farming continues to gain popularity, effective herbicides are increasingly needed. Compositions with effective weed control and low application rates lead to increased crop yields and reduced environmental, human, and mammalian health concerns. [Overview of the project]

[0011] In various embodiments, the present invention relates to compounds represented by the structures of formulas I, I(a) to I(ga), X, and X(a) to X(d) as defined herein, or to pesticide-acceptable salts, stereoisomers, tautomers, hydrates, N-oxides, reverse amide analogs, isotopic variants (e.g., deuterated analogs), or any combination thereof.

[0012] In various embodiments, the present invention relates to a compound represented by the structure of formula I(g),

[0013] [ka]

[0014] During the ceremony, R1, R1', R2, R2', and R 40 However, each is independently H, C1-C5 linear or branched, unsubstituted alkyl, methyl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl, benzyl, C(O)-R10 , or C(O)-CH3, R3 is either OH or NH2. R4 is either NH2 or OH. If R3 is OH, then R4 is NH2, and if R3 is NH2, then R4 is OH. If R3 is OH and R4 is NH2, then n+m cannot be equal to 3. Alternatively, R3 and R4 may be linked together to form ring A represented by the following structure,

[0015] [ka]

[0016] R5 is H, C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, CH2SH, ethyl, butyl, CH2-CCH, isopropyl, CH2-C(O)-OCH3), C2-C5 linear or branched, substituted or unsubstituted alkenyl, C2-C5 linear or branched, substituted or unsubstituted alkynyl (e.g., CCH, CH2-CCH), C1-C5 linear or branched haloalkyl (e.g., CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2), R8-aryl (e.g., CH2-Ph), C(=CH2)-R 10 (For example, C(=CH2)-C(O)-OCH3, C(=CH2)-CN), substituted or unsubstituted alkyl sulfones (for example, SO2-CH2-cyclopentyl), substituted or unsubstituted aryl compounds (for example, phenyl), substituted or unsubstituted heteroaryl compounds (for example, pyridine (2,3, and 4-pyridine)), R 10 However, it is H, CN, C1-C5 linear or branched alkyl, C(O)R, or S(O)2R. R is a C1-C5 linear or branched alkyl, a C1-C5 linear or branched alkoxy, a phenyl, an aryl, or a heteroaryl. m is 1 or 2, n is 0, 1, 2, or 3, X1 is S, O, or CH2, X2 is S, O, or CH2. This relates to compounds, or their pesticide-permissible salts, stereoisomers, tautomers, hydrates, N-oxides, reverse amide analogs, isotopic variants (e.g., deuterated analogs), or any combination thereof.

[0017] In some embodiments, ring A has two chiral centers. In some embodiments, the compound is not (6R,7S)-6-amino-7-hydroxyoctanoic acid or 5-((4R,5S)-5-methyl-2-oxoxazolidine-4-yl)pentanoic acid. In some embodiments, the compound is a substantially pure single stereoisomer. In some embodiments, the compound is a mixture of stereoisomers. In some embodiments, the compound is a substantially pure SR stereoisomer. In some embodiments, the compound is a substantially pure RS stereoisomer. In some embodiments, the substantially pure stereoisomer has a purity of more than 90%. In some embodiments, the substantially pure stereoisomer has a purity of more than 95%. In some embodiments, the substantially pure stereoisomer has a purity of more than 98%. In some embodiments, the compound is one of the compounds 101, 102, 104, 105, 113, 114, 115, 116, 117, 118, 119, 120, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 137, 138, 139, 140, 141, 142, or a pesticide-acceptable salt, stereoisomer, tautomer, hydrate, N-oxide, reverse amide analog, or isotopic variant thereof, each representing a separate embodiment according to the present invention.

[0018] In various embodiments, the present invention relates to herbicidal compounds represented by the structures of Formula I, I(a)-(ga), X, and X(a)-(d) as defined hereinbelow, or pesticidal salts, stereoisomers, tautomers, hydrates, N-oxides, reverse amide analogs, or isotope variants (e.g., deuterated analogs) thereof, each representing a distinct embodiment of the present invention.

[0019] In various embodiments, the present invention is a herbicidal compound represented by the structure of Formula I(ga), wherein

[0020] [Chemical Formula]

[0021] wherein C A and C B are both chiral carbon centers, or C A and C B are linked together with R3 and R4 to form a ring A represented by the following structure

[0022] [Chemical Formula]

[0023] R1, R1', R2, R2', and R 40 are each independently H, a C1-C5 straight-chain or branched, unsubstituted alkyl, methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl, benzyl, C(O)-R 10 or C(O)-CH3 R3 is OH, SH, NH2, NHNH2, NHR, N(R)2, NHC(O)OBz, -NHC(O)-R 10, NHC(O)CH3, C1-C5 linear or branched, substituted or unsubstituted alkyl, methyl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl, substituted or unsubstituted C3-C8 cycloalkyl, C1-C5 linear or branched, or C3-C8 cyclic haloalkyl, C1-C5 linear or branched, or C3-C8 cyclic alkoxy, substituted or unsubstituted C3-C8 heterocyclic ring, or substituted or unsubstituted aryl, R4 is NH2, NHNH2, N(R)2, -NHC(O)-R 10 , NHC(O)H, NHC(O)CH3, C1-C5 linear or branched, substituted or unsubstituted alkyl, C1-C5 linear or branched, or C3-C8 cyclic haloalkyl, C1-C5 linear or branched, or C3-C8 cyclic alkoxy, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C3-C8 heterocyclic ring, or substituted or unsubstituted aryl, Alternatively, R3 and R4 may connect together to form the ring A described above. Both R3 and R4 cannot be NH2. If R3 is OH and R4 is NH2, then n+m cannot be equal to 3. R5 is H, C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, CH2SH, ethyl, butyl, CH2-CCH, isopropyl, CH2-C(O)-OCH3), C2-C5 linear or branched, substituted or unsubstituted alkenyl, C2-C5 linear or branched, substituted or unsubstituted alkynyl (e.g., CCH, CH2-CCH), C1-C5 linear or branched haloalkyl (e.g., CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2), R8-aryl (e.g., CH2-Ph), C(=CH2)-R 10(For example, C(=CH2)-C(O)-OCH3, C(=CH2)-CN), substituted or unsubstituted alkyl sulfones (for example, SO2-CH2-cyclopentyl), substituted or unsubstituted aryl compounds (for example, phenyl), substituted or unsubstituted heteroaryl compounds (for example, pyridine (2,3, and 4-pyridine)), R8 is [CH2] p And, p is between 1 and 10. R 10 and R 11 However, each is independently H, CN, C1-C5 linear or branched alkyl, C(O)R, or S(O)2R, Or R 10 and R 11 However, they are linked together to form a substituted or unsubstituted C3-C8 heterocycle. R is either a C1-C5 linear or branched alkyl, a C1-C5 linear or branched alkoxy, a phenyl, an aryl, or a heteroaryl, or two gem R substituents are linked together to form a 5 or 6-membered heterocyclic ring. m is 1 or 2, n is 0, 1, 2, or 3, X1 is S, O, or CH2, X2 is S, O, or CH2. This relates to herbicidal compounds, or their pesticide-permissible salts, stereoisomers, tautomers, hydrates, N-oxides, reverse amide analogs, isotopic variants (e.g., deuterated analogs), or any combination thereof.

[0024] In some embodiments, the present invention relates to a herbicidal compound represented by the structure of any one of Compounds 101, 102, 104-120, 123-134, 137-178, or a pharmaceutically acceptable salt, stereoisomer, tautomer, hydrate, N-oxide, reverse amide analogue, or isotope variant thereof, each representing a separate embodiment of the present invention. In some embodiments, the compound is a compound that is any one of the compounds listed in Table 2 below in this specification, or a salt, stereoisomer, tautomer, hydrate, N-oxide, reverse amide analogue, or isotope variant thereof that is acceptable as an agricultural chemical, each representing a separate embodiment of the present invention.

[0025] In some embodiments, the present invention is a herbicidal compound represented by the structure of Formula X(a), wherein

[0026]

Chemical formula

[0027] wherein R5 is H, C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, CH2SH, ethyl, butyl, CH2-CCH, iso-propyl, CH2-C(O)-OCH3), C2-C5 linear or branched, substituted or unsubstituted alkenyl, C2-C5 linear or branched, substituted or unsubstituted alkynyl (e.g., CCH, CH2-CCH), C1-C5 linear or branched haloalkyl (e.g., CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2), R8-aryl (e.g., CH2-Ph), C(=CH2)-R 10 (e.g., C(=CH2)-C(O)-OCH3, C(=CH2)-CN), substituted or unsubstituted aryl (e.g., phenyl), substituted or unsubstituted heteroaryl (e.g., pyridine (2, 3, and 4-pyridine)), R8 is [CH2] p and p is between 1 and 10. R9, [CH] q [C] q And, q is between 2 and 10, R 10 and R 11 However, each is independently either H, CN, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH3)), or S(O)2R, or R 10 and R 11 However, they link together to form substituted or unsubstituted C3-C8 heterocyclic rings (e.g., piperazine, piperidine), The substitution includes F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl (e.g., imidazole), C3-C8 cycloalkyl (e.g., cyclohexyl), CN, NO2, or any combination thereof. R is H, a C1-C5 linear or branched alkyl (e.g., methyl, ethyl), a C1-C5 linear or branched alkoxy (e.g., methoxy), a phenyl, an aryl, or a heteroaryl, or two gem R substituents are linked together to form a 5 or 6-membered heterocyclic ring. X1 is S, O, CH2, CH(R), or C(R)2. n and o are each independent integers between 0 and 2. m is an integer between 1 and 3. This relates to herbicidal compounds, or their pesticide-permissible salts, stereoisomers, tautomers, hydrates, N-oxides, reverse amide analogs, isotopic variants (e.g., deuterated analogs), or any combination thereof.

[0028] In various embodiments, the present invention relates to a compound represented by the structure of formula X(a) as defined above herein, where n is 2, o is 0, and if X1 is CH2, R5 cannot be H.

[0029] In some embodiments, the present invention relates to a herbicide compound represented by the structure of formula X(b),

[0030] [ka]

[0031] During the ceremony, R5 is H, C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, CH2SH, ethyl, butyl, CH2-CCH, isopropyl, CH2-C(O)-OCH3), C2-C5 linear or branched, substituted or unsubstituted alkenyl, C2-C5 linear or branched, substituted or unsubstituted alkynyl (e.g., CCH, CH2-CCH), C1-C5 linear or branched haloalkyl (e.g., CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2), R8-aryl (e.g., CH2-Ph), C(=CH2)-R 10 (For example, C(=CH2)-C(O)-OCH3, C(=CH2)-CN), substituted or unsubstituted aryls (for example, phenyl), substituted or unsubstituted heteroaryls (for example, pyridine (2,3, and 4-pyridine)), R8 is [CH2] p And, p is between 1 and 10. R 10 However, it is H, CN, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH3)), or S(O)2R. R is H, a C1-C5 linear or branched alkyl (e.g., methyl, ethyl), a C1-C5 linear or branched alkoxy (e.g., methoxy), a phenyl, an aryl, or a heteroaryl, or two gem R substituents are linked together to form a 5 or 6-membered heterocyclic ring. X1 is S, O, CH2, CH(R), or C(R)2. X2 is S, O, CH2, CH(R), or C(R)2. n is an integer between 0 and 2. m is an integer between 1 and 3. This relates to herbicidal compounds, or their pesticide-permissible salts, stereoisomers, tautomers, hydrates, N-oxides, reverse amide analogs, isotopic variants (e.g., deuterated analogs), or any combination thereof.

[0032] In various embodiments, the present invention relates to a herbicide compound represented by the structure of formula X(c),

[0033] [ka]

[0034] During the ceremony, R5 is H, C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, CH2SH, ethyl, butyl, CH2-CCH, isopropyl, CH2-C(O)-OCH3), C2-C5 linear or branched, substituted or unsubstituted alkenyl, C2-C5 linear or branched, substituted or unsubstituted alkynyl (e.g., CCH, CH2-CCH), C1-C5 linear or branched haloalkyl (e.g., CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2), R8-aryl (e.g., CH2-Ph), C(=CH2)-R 10 (For example, C(=CH2)-C(O)-OCH3, C(=CH2)-CN), substituted or unsubstituted aryls (for example, phenyl), substituted or unsubstituted heteroaryls (for example, pyridine (2,3, and 4-pyridine)), R8 is [CH2] p And, p is between 1 and 10. R9, [CH] q [C] q And, q is between 2 and 10, R 10 and R 11 However, each is independently either H, CN, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH3)), or S(O)2R, or R 10 and R 11 However, they link together to form substituted or unsubstituted C3-C8 heterocyclic rings (e.g., piperazine, piperidine), The substitution includes F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl (e.g., imidazole), C3-C8 cycloalkyl (e.g., cyclohexyl), CN, NO2, or any combination thereof. R is H, a C1-C5 linear or branched alkyl (e.g., methyl, ethyl), a C1-C5 linear or branched alkoxy (e.g., methoxy), a phenyl, an aryl, or a heteroaryl, or two gem R substituents are linked together to form a 5 or 6-membered heterocyclic ring. X1 is S, O, CH2, CH(R), or C(R)2. X2 is S, O, CH2, CH(R), or C(R)2. n is an integer between 0 and 2. m is an integer between 1 and 3. This relates to herbicidal compounds, or their pesticide-permissible salts, stereoisomers, tautomers, hydrates, N-oxides, reverse amide analogs, isotopic variants (e.g., deuterated analogs), or any combination thereof.

[0035] In various embodiments, the present invention relates to a compound represented by the structure of formula X(c) herein, wherein n is an integer from 1 to 2, or an agriculturally acceptable salt, stereoisomer, tautomer, hydrate, N-oxide, reverse amide analog, isotope variant (e.g., deuterated analog) thereof, or any combination thereof.

[0036] In various embodiments, the present invention is a herbicidal compound represented by the structure of formula X(d),

[0037]

Chemical formula

[0038] wherein, R5 is H, C1-C5 straight-chain or branched, substituted or unsubstituted alkyl (e.g., methyl, CH2SH, ethyl, butyl, CH2-CCH, iso-propyl, CH2-C(O)-OCH3), C2-C5 straight-chain or branched, substituted or unsubstituted alkenyl, C2-C5 straight-chain or branched, substituted or unsubstituted alkynyl (e.g., CCH, CH2-CCH), C1-C5 straight-chain or branched haloalkyl (e.g., CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2), R8-aryl (e.g., CH2-Ph), C(=CH2)-R 10 (e.g., C(=CH2)-C(O)-OCH3, C(=CH2)-CN), substituted or unsubstituted aryl (e.g., phenyl), substituted or unsubstituted heteroaryl (e.g., pyridine (2, 3, and 4-pyridine)), R8 is [CH2] p and p is from 1 to 10, R9 is [CH] q [C] q and q is from 2 to 10, R 10 and R 11However, each is independently either H, CN, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH3)), or S(O)2R, or R 10 and R 11 However, they link together to form substituted or unsubstituted C3-C8 heterocyclic rings (e.g., piperazine, piperidine), The substitution includes F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl (e.g., imidazole), C3-C8 cycloalkyl (e.g., cyclohexyl), CN, NO2, or any combination thereof. R is H, a C1-C5 linear or branched alkyl (e.g., methyl, ethyl), a C1-C5 linear or branched alkoxy (e.g., methoxy), a phenyl, an aryl, or a heteroaryl, or two gem R substituents are linked together to form a 5 or 6-membered heterocyclic ring. X2 is S, O, CH2, CH(R), or C(R)2. n is an integer between 0 and 2. m is an integer between 1 and 3. This relates to herbicidal compounds, or their pesticide-permissible salts, stereoisomers, tautomers, hydrates, N-oxides, reverse amide analogs, isotopic variants (e.g., deuterated analogs), or any combination thereof.

[0039] In various embodiments, the present invention relates to a compound represented herein by the structure of formula X(d) above, wherein m is 1 or 3, or to a pesticide-acceptable salt, stereoisomer, tautomer, hydrate, N-oxide, reverse amide analog, isotopic variant (e.g., deuterated analog), or any combination thereof.

[0040] In various embodiments, the present invention relates to a pesticide composition containing an effective amount of the compound according to the present invention for herbicidal purposes.

[0041] In various embodiments, the present invention relates to a method for controlling undesirable plant growth, comprising applying a compound or pesticide composition according to the present invention to farmland.

[0042] In various embodiments, the present invention relates to compounds or pesticide compositions according to the present invention for use in controlling the growth of undesirable plants. In some embodiments, the plants are eudicots (dicotyledons) or monocots (monocotyledons). In some embodiments, the plants are weeds. In some embodiments, the weeds include Abutilon theophrasti, Amaranthus palmeri, Ambrosia artemisiifolia, Alopecurus myosuroides, Avena sterilis, Chenopodium album, Conyza Canadensis, Digitalia sanguinalis, Echinochloa colona, ​​Euphorbia heterophylla, Lolium perenne, Lolium rigidum, Matricaria chamomilla, Phalaris paradoxa, Poa annua, Portulaca oleracea, Setaria viridis, Solanum nigrum, or any combination thereof. In some embodiments, the dicotyledonous plant is Arabidopsis thaliana and / or the monocotyledonous plant is Dactyloctenium aegyptium or Eragrostis teff. In some embodiments, the compounds are for use in pre-planting treatment, pre-emergence treatment, post-emergence treatment, or any combination thereof, each representing a separate embodiment according to the present invention. [Modes for carrying out the invention]

[0043] In various embodiments, the present invention relates to a compound represented by the structure of formula (I),

[0044] [ka]

[0045] During the ceremony, Rings A and B are either absent, or each independently exists as a substituted or unsubstituted single or condensed aromatic system or a heteroaromatic ring system (e.g., B: aryl, pyridine), or a substituted or unsubstituted single or condensed C3-C 10 Cycloalkyl (e.g., cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl), or substituted or unsubstituted single or condensed C3-C 10 Heterocyclic compounds (e.g., A:5-methyloxazolidine-2-one, 1,2, or 3-pyrrolidine, tetrahydropyridine, 5,6-dihydro-4H-1,3-thiazine, 4,5-dihydro-1H-imidazole, pyridine, tetrahydropyrimidine, piperidine, imidazole), R1, R1', R2, R2', and R 40 However, each is independent of the others: H, F, Cl, Br, I, OH, SH, R8-OH (e.g., CH2-OH), R8-SH, -R8-OR 10 , (e.g., -CH2-O-CH3), R8-(C3-C8 cycloalkyl) (e.g., cyclohexyl), R8-(C3-C8 heterocyclic ring) (e.g., CH2-imidazole, CH2-indazole), CF3, CD3, OCD3, CN, NO2, -CH2CN, -R8CN, NH2, NHR, N(R)2, R8-N(R 10 )(R 11 )(For example, CH2-NH2, CH2-N(CH3)2), R9-R8-N(R 10 )(R 11 (For example, C≡C-CH2-NH2), B(OH)2, -OC(O)CF3, -OCH2Ph, NHC(O)-R 10 (For example, NHC(O)CH3), NHC(O)-N(R 10 )(R 11(For example, NHC(O)N(CH3)2), COOH, -C(O)Ph, C(O)OR 10 (e.g. C(O)O-CH3, C(O)O-CH(CH3)2, C(O)O-CH2CH3), R8-C(O)-R 10 (For example, CH2C(O)CH3), C(O)H, C(O)-R 10 (e.g., C(O)-CH3, C(O)-CH2CH3, C(O)-CH2CH2CH3), C1-C5 linear or branched C(O)-haloalkyl (e.g., C(O)-CF3), -C(O)NH2, C(O)NHR, C(O)N(R) 10 )(R 11 )(For example, C(O)N(CH3)2), SO2R, SO2N(R 10 )(R 11)(e.g., SO2N(CH3)2, SO2NHC(O)CH3, C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, 2, 3, or 4-CH2-C6H4-Cl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl, benzyl), C1-C5 linear or branched, substituted or unsubstituted alkenyl (e.g., CH=C(Ph)2), C1-C5 linear or branched, or C3-C8 cyclic haloalkyl (e.g., CF3, CF2CH3, C H2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2), C1-C5 linear or branched, or C3-C8 cyclic alkoxy (e.g., methoxy, ethoxy, propoxy, isopropoxy, O-CH2-cyclopropyl, O-cyclobutyl, O-cyclopentyl, O-cyclohexyl, 1-butoxy, 2-butoxy, O-tBu) (optionally, at least one methylene group (CH2) in the alkoxy is an oxygen atom ( For example, substituted with O-1-oxacyclobutyl, O-2-oxacyclobutyl), C1-C5 linear or branched thioalkoxys, C1-C5 linear or branched haloalkoxys (e.g., OCF3, OCHF2), C1-C5 linear or branched alkoxyalkyls, substituted or unsubstituted C3-C8 cycloalkyls (e.g., cyclopropyl, cyclopentyl), substituted or unsubstituted C3-C8 heterocyclic rings (e.g., 3-methyl-4H-1,2,4-triazole, 5-methyl-1,2,4 -Oxadiazole, thiophene, oxazole, oxadiazole, imidazole, furan, triazole, tetrazole, pyridine (2, 3, or 4-pyridine), 3-methyl-2-pyridine, pyrimidine, pyrazine, oxacyclobutane (1 or 2-oxacyclobutane, protonated or deprotonated pyridine oxide), substituted or unsubstituted aryl (e.g., phenyl), substituted or unsubstituted benzyl (e.g., benzyl, 4-Cl-benzyl, 4-OH-benzyl), Alternatively, R2 and R1 may be linked together to form a C3-C8 substituted or unsubstituted, carbocyclic or heterocyclic ring. R3 can be H, F, Cl, Br, I, OH, SH, =O, R8-OH (e.g., CH2-OH), R8-SH, -R8-OR10 (For example, CH2-O-CH3)CF3, CD3, OCD3, CN, NO2, -CH2CN, -R8CN, NH2, NHNH2, NHR, N(R)2, R8-N(R 10 )(R 11 )(For example, CH2-NH2, CH2-N(CH3)2), R9-R8-N(R 10 )(R 11 ), B(OH)2, -OC(O)CF3, -OCH2Ph, NHC(O)OBz, -NHC(O)-R 10 (For example, NHC(O)CH3), NHC(O)-N(R 10 )(R 11 (For example, NHC(O)N(CH3)2), COOH, -C(O)Ph, C(O)OR 10 (For example, C(O)O-CH3, C(O)O-CH2CH3), R8-C(O)-R 10 (For example, CH2C(O)CH3), C(O)H, C(O)-R 10 (e.g., C(O)-CH3, C(O)-CH2CH3, C(O)-CH2CH2CH3), C1-C5 linear or branched C(O)-haloalkyl (e.g., C(O)-CF3), -C(O)NH2, C(O)NHR, C(O)N(R) 10 )(R 11 )(For example, C(O)N(CH3)2), SO2R, SO2N(R 10 )(R 11)(e.g., SO2N(CH3)2), C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, C(OH)(CH3)(Ph), ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl), C1-C5 linear or branched, or C3-C8 cyclic haloalkyl (e.g., CF3, CF2CH3, CF2-cyclobutyl, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2), C1-C5 linear or branched, or C3-C8 cyclic alkoxy (e.g., methoxy, ethoxy, propoxy, isopropoxy, O-CH2-cyclopropyl ), C1-C5 linear or branched thiooxy, C1-C5 linear or branched haloalkoxy, C1-C5 linear or branched alkoxyalkyl, substituted or unsubstituted C3-C8 cycloalkyl (e.g., cyclopropyl, cyclopentyl), substituted or unsubstituted C3-C8 heterocyclic ring (e.g., 3-methyl-4H-1,2,4-triazole, 5-methyl-1,2,4-oxadiazole, thiophene, oxazole, isoxazole, imidazole, furan, triazole, pyridine (2,3, or 4-pyridine), pyrimidine, pyrazine, oxacyclobutane (1 or 2-oxacyclobutane)), substituted or unsubstituted aryl (e.g., phenyl), Alternatively, R3 and R2 may link together to form a C3-C8 substituted or unsubstituted, carbocyclic or heterocyclic ring (e.g., cyclopropyl). R4 can be H, F, Cl, Br, I, OH, SH, =O, =NH-OH, R8-OH (e.g., CH2-OH), R8-SH, -R8-OR 10 (For example, CH2-O-CH3)CF3, CD3, OCD3, CN, NO2, -CH2CN, -R8CN, NH2, NHNH2, NHR, N(R)2, R8-N(R 10 )(R 11 )(For example, CH2-NH2, CH2-N(CH3)2)R9-R8-N(R 10 )(R 11 ), B(OH)2, -OC(O)CF3, -OCH2Ph, NHC(O)OBz, -NHC(O)-R 10 (For example, NHC(O)CH, NHC(O)H3), NHC(O)-N(R10 )(R 11 )(e.g., NHC(O)N(CH3)2), COOH, -C(O)Ph, C(O)O-R 10 (e.g., C(O)O-CH3, C(O)O-CH2CH3), R8-C(O)-R 10 (e.g., CH2C(O)CH3), C(O)H, C(O)-R 10 (e.g., C(O)-CH3, C(O)-CH2CH3, C(O)-CH2CH2CH3), C1-C5 linear or branched C(O)-haloalkyl (e.g., C(O)-CF3), -C(O)NH2, C(O)NHR, C(O)N(R 10 )(R 11 )(e.g., C(O)N(CH3)2), SO2R, SO2N(R 10 )(R 11 )(e.g., SO2N(CH3)2), C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, C(OH)(CH3)(Ph), ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl), C1-C5 linear or branched, or C3-C8 cyclic haloalkyl (e.g., CF3, CF2CH3, CF2-cyclobutyl, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2), C1-C5 linear or branched, or C3-C8 cyclic alkoxy (e.g., methoxy, ethoxy, propoxy, isopropoxy, O-CH2-cyclopropyl), C1-C5 linear or branched thiooxy, C1-C5 linear or branched haloalkoxy, C1-C5 linear or branched alkoxyalkyl, substituted or unsubstituted C3-C8 cycloalkyl (e.g., cyclopropyl, cyclopentyl), substituted or unsubstituted C3-C8 heterocyclic ring (e.g., 3-methyl-4H-1,2,4-triazole, 5-methyl-1,2,4-oxadiazole, thiophene, oxazole, isoxazole, imidazole, furan, triazole, pyridine (2, 3, or 4-pyridine), pyrimidine, pyrazine, oxacyclobutane (1 or 2-oxacyclobutane), indole), substituted or unsubstituted aryl (e.g., phenyl), or <( Alternatively, R3 and R4 are linked together to form a ring A as defined above (e.g., cyclopropyl, 5-methyloxazolidin-2-one), R5 is H, C1-C5 straight-chain or branched, substituted or unsubstituted alkyl (e.g., methyl, CH2SH, ethyl, butyl, CH2-CCH, iso-propyl, CH2-C(O)-OCH3), C2-C5 straight-chain or branched, substituted or unsubstituted alkenyl, C2-C5 straight-chain or branched, substituted or unsubstituted alkynyl (e.g., CCH, CH2-CCH), C1-C5 straight-chain or branched haloalkyl (e.g., CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2), R8-aryl (e.g., CH2-Ph), C(=CH2)-R 10 (e.g., C(=CH2)-C(O)-OCH3, C(=CH2)-CN), substituted or unsubstituted alkyl sulfone (e.g., SO2-CH2-cyclopentyl), substituted or unsubstituted aryl (e.g., phenyl), substituted or unsubstituted heteroaryl (e.g., pyridine (2, 3, and 4-pyridine)), R8 is [CH2] p and, p is from 1 to 10, R9 is [CH] q , [C] q and, q is from 2 to 10, R 10 and R 11 are each independently H, CN, C1-C5 straight-chain or branched alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH3)), or S(O)2R, or alternatively R 10 and R 11 are linked together to form a substituted or unsubstituted C3-C8 heterocyclic ring (e.g., piperazine, piperidine), R is H, a C1-C5 linear or branched alkyl (e.g., methyl, ethyl), a C1-C5 linear or branched alkoxy (e.g., methoxy), a phenyl, an aryl, or a heteroaryl, or two gem R substituents are linked together to form a 5 or 6-membered heterocyclic ring. m is an integer between 1 and 5 (for example, 1 or 2), n is an integer between 0 and 5 (for example, 0, 1, 2, or 3), X1 is S, O, N-OH, CH2, C(R)2, or N-OMe. Is X2 S, O, N-OH, CH2, C(R)2, or N-OMe? Alternatively, X2 may link with the adjacent carbon to X1 to form a ring B as defined above. X3 is O, NH, or NR 50 And, R 50 However, this relates to compounds that are H or C1-C5 linear or branched, substituted or unsubstituted alkyl groups, or their pesticide-acceptable salts, stereoisomers, tautomers, hydrates, N-oxides, reverse amide analogs, isotopic variants (e.g., deuterated analogs), or any combination thereof.

[0046] In some embodiments, R3 and R4 are linked together to form ring A. In some embodiments, ring B is absent. In some embodiments, R3 is OH or NH2. In some embodiments, R4 is NH2 or OH. In some embodiments, both R3 and R4 cannot be NH2. In some embodiments, if R3 is OH, then R4 is NH2. In some embodiments, if R3 is NH2, then R4 is OH. In some embodiments, if R3 is OH, then R4 is NH2, and if R3 is NH2, then R4 is OH. In some embodiments, if R3 is OH and R4 is NH2, then n+m cannot be equal to 3. In some embodiments, the compounds are compounds 101, 102, 104, 105, 106, 113, 114, 115, 116, 117, 118, 119, or 120, each representing a distinct embodiment according to the present invention. In some embodiments, ring A has two chiral centers. In some embodiments, the compound is not (6R,7S)-6-amino-7-hydroxyoctanoic acid. In some embodiments, the compound is not 5-((4R,5S)-5-methyl-2-oxoxazolidine-4-yl)pentanoic acid. In some embodiments, the compound is substantially a pure single stereoisomer. In some embodiments, R1 and R1' are both H. In some embodiments, R2 is CH3 or CH2CH3. In some embodiments, R2' is H or CH3. In some embodiments, R 40R5 is CH3 or H. In some embodiments, X1 is CH2. In some embodiments, X2 is CH2. In some embodiments, X3 is O, NH, or N-CH3. In some embodiments, R5 is H, or a C1-C5 linear or branched substituted or unsubstituted alkyl, or a substituted or unsubstituted alkyl sulfone. In some embodiments, R5 is a substituted or unsubstituted alkyl. In some embodiments, R5 is H. In some embodiments, R5 is H, ethyl, butyl, CH2-CCH, CH2-C(O)-OCH3, or SO2-CH2-cyclopentyl, each being a separate embodiment of the present invention. In some embodiments, n is 0, 1, 2, or 3. In some embodiments, n is 1. In some embodiments, m is 1 or 2. In some embodiments, m is 1.

[0047] In some embodiments, n is 0. In some embodiments, A is a substituted aryl (e.g., 2-aminophenyl). In some embodiments, A is a substituted or unsubstituted cycloalkyl (e.g., cyclopentyl, cyclohexyl). In some embodiments, the substitution is at least one selected from F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl, C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl, C3-C8 cycloalkyl, CN, and NO2, each representing a distinct embodiment according to the present invention.

[0048] In some embodiments, A is a substituted cycloalkyl. In some embodiments, A is a substituted cyclopropyl. In some embodiments, A is a substituted cyclobutyl. In some embodiments, A is a substituted cyclopentyl. In some embodiments, A is a substituted cyclohexyl. In some embodiments, A is substituted with at least an amine. In some embodiments, A is substituted with at least NH2. In some embodiments, A is substituted with NH2. In some embodiments, A is a cycloalkyl that is substituted with at least an amine. In some embodiments, A is a cycloalkyl that is substituted with NH2. In some embodiments, A is a 5 or 6-membered nitrogen-containing heterocyclic ring. In some embodiments, A is a 1, 2, or 3-piperidine, oxazolidine-2-one, tetrahydropyrimidine, pyridine, dihydrothiaidine, dihydroimidazole, tetrahydropyridine, or pyrrolidine, which may be substituted or unsubstituted, each being a separate embodiment of the present invention. In some embodiments, A is substituted with an amine. In some embodiments, A is substituted with at least NH2.

[0049] In some embodiments, B is absent. In some embodiments, B is pyridine.

[0050] In some embodiments, R1, R1', R2, R2', and R 40 Each of these is independently H, or a C1-C5 linear or branched substituted or unsubstituted alkyl (e.g., methyl, ethyl).

[0051] In some embodiments, substitutions include F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl (e.g., imidazole), C3-C8 cycloalkyl (e.g., cyclohexyl), CN, NO2, or any combination thereof.

[0052] In some embodiments, the compound is one of the compounds listed in Table 1. In various embodiments, the compound is a herbicide compound. In various embodiments, the compound is intended for use in controlling undesirable plant growth. In some embodiments, the compound is one of the compounds listed in Table 2.

[0053] In various embodiments, the present invention relates to a compound represented by the structure of formula I(a),

[0054] [ka]

[0055] During the ceremony, C A and C B However, both are chiral carbon centers, or C A and C B However, together with R3 and R4, they form ring A represented by the following structure,

[0056] [ka]

[0057] R1, R1', R2, R2', and R 40However, each is independent of the others: H, F, Cl, Br, I, OH, SH, R8-OH (e.g., CH2-OH), R8-SH, -R8-OR 10 , (e.g., -CH2-O-CH3), R8-(C3-C8 cycloalkyl) (e.g., cyclohexyl), R8-(C3-C8 heterocyclic ring) (e.g., CH2-imidazole, CH2-indazole), CF3, CD3, OCD3, CN, NO2, -CH2CN, -R8CN, NH2, NHR, N(R)2, R8-N(R 10 )(R 11 )(For example, CH2-NH2, CH2-N(CH3)2), R9-R8-N(R 10 )(R 11 (For example, C≡C-CH2-NH2), B(OH)2, -OC(O)CF3, -OCH2Ph, NHC(O)-R 10 (For example, NHC(O)CH3), NHC(O)-N(R 10 )(R 11 (For example, NHC(O)N(CH3)2), COOH, -C(O)Ph, C(O)OR 10 (e.g. C(O)O-CH3, C(O)O-CH(CH3)2, C(O)O-CH2CH3), R8-C(O)-R 10 (For example, CH2C(O)CH3), C(O)H, C(O)-R 10 (e.g., C(O)-CH3, C(O)-CH2CH3, C(O)-CH2CH2CH3), C1-C5 linear or branched C(O)-haloalkyl (e.g., C(O)-CF3), -C(O)NH2, C(O)NHR, C(O)N(R) 10 )(R 11 )(For example, C(O)N(CH3)2), SO2R, SO2N(R 10 )(R 11)(e.g., SO2N(CH3)2, SO2NHC(O)CH3), C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, 2, 3, or 4-CH2-C6H4-Cl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl, benzyl), C1-C5 linear or branched, substituted or unsubstituted alkenyl (e.g., CH=C(Ph)2), C1-C5 linear or branched, or C3-C8 cyclic haloalkyl (e.g., CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2), C1-C5 linear or branched, or C3-C8 cyclic alkoxys (e.g., methoxy, ethoxy, propoxy, isopropoxy, O-CH2-cyclopropyl, O-cyclobutyl, O-cyclopentyl, O-cyclohexyl, 1-butoxy, 2-butoxy, O-tBu) (optionally, at least one methylene group (CH2) in the alkoxy is an oxygen atom (For example, substituted by O-1-oxacyclobutyl, O-2-oxacyclobutyl), C1-C5 linear or branched thioalkoxys, C1-C5 linear or branched haloalkoxys (for example, OCF3, OCHF2), C1-C5 linear or branched alkoxyalkyls, substituted or unsubstituted C3-C8 cycloalkyls (for example, cyclopropyl, cyclopentyl), substituted or unsubstituted C3-C8 heterocyclic rings (for example, 3-methyl-4H-1,2,4-triazole, 5-methyl-1,2,4) -Oxadiazole, thiophene, oxazole, oxadiazole, imidazole, furan, triazole, tetrazole, pyridine (2, 3, or 4-pyridine), 3-methyl-2-pyridine, pyrimidine, pyrazine, oxacyclobutane (1 or 2-oxacyclobutane, protonated or deprotonated pyridine oxide), substituted or unsubstituted aryl (e.g., phenyl), substituted or unsubstituted benzyl (e.g., benzyl, 4-Cl-benzyl, 4-OH-benzyl), Alternatively, R2 and R1 may be linked together to form a substituted or unsubstituted C3-C8 carboncyclic or heterocyclic ring. R3 can be H, F, Cl, Br, I, OH, SH, =O, R8-OH (e.g., CH2-OH), R8-SH, -R8-OR10 (For example, CH2-O-CH3)CF3, CD3, OCD3, CN, NO2, -CH2CN, -R8CN, NH2, NHNH2, NHR, N(R)2, R8-N(R 10 )(R 11 )(For example, CH2-NH2, CH2-N(CH3)2), R9-R8-N(R 10 )(R 11 ), B(OH)2, -OC(O)CF3, -OCH2Ph, NHC(O)OBz, -NHC(O)-R 10 (For example, NHC(O)CH3), NHC(O)-N(R 10 )(R 11 (For example, NHC(O)N(CH3)2), COOH, -C(O)Ph, C(O)OR 10 (For example, C(O)O-CH3, C(O)O-CH2CH3), R8-C(O)-R 10 (For example, CH2C(O)CH3), C(O)H, C(O)-R 10 (e.g., C(O)-CH3, C(O)-CH2CH3, C(O)-CH2CH2CH3), C1-C5 linear or branched C(O)-haloalkyl (e.g., C(O)-CF3), -C(O)NH2, C(O)NHR, C(O)N(R) 10 )(R 11 )(For example, C(O)N(CH3)2), SO2R, SO2N(R 10 )(R 11)(e.g., SO2N(CH3)2), C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, C(OH)(CH3)(Ph), ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl), C1-C5 linear or branched, or C3-C8 cyclic haloalkyl (e.g., CF3, CF2CH3, CF2-cyclobutyl, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2), C1-C5 linear or branched, or C3-C8 cyclic alkoxy (e.g., methoxy, ethoxy, propoxy, isopropoxy, O-CH2-cyclopropyl ), C1-C5 linear or branched thiooxy, C1-C5 linear or branched haloalkoxy, C1-C5 linear or branched alkoxyalkyl, substituted or unsubstituted C3-C8 cycloalkyl (e.g., cyclopropyl, cyclopentyl), substituted or unsubstituted C3-C8 heterocyclic ring (e.g., 3-methyl-4H-1,2,4-triazole, 5-methyl-1,2,4-oxadiazole, thiophene, oxazole, isoxazole, imidazole, furan, triazole, pyridine (2,3, or 4-pyridine), pyrimidine, pyrazine, oxacyclobutane (1 or 2-oxacyclobutane)), substituted or unsubstituted aryl (e.g., phenyl), Alternatively, R3 and R2 may link together to form a C3-C8 substituted or unsubstituted, carbocyclic or heterocyclic ring (e.g., cyclopropyl). R4 can be H, F, Cl, Br, I, OH, SH, =O, =NH-OH, R8-OH (e.g., CH2-OH), R8-SH, -R8-OR 10 (For example, CH2-O-CH3)CF3, CD3, OCD3, CN, NO2, -CH2CN, -R8CN, NH2, NHNH2, NHR, N(R)2, R8-N(R 10 )(R 11 )(For example, CH2-NH2, CH2-N(CH3)2), R9-R8-N(R 10 )(R 11 ), B(OH)2, -OC(O)CF3, -OCH2Ph, NHC(O)OBz, -NHC(O)-R 10 (For example, NHC(O)CH, NHC(O)H3), NHC(O)-N(R10 )(R 11 (For example, NHC(O)N(CH3)2), COOH, -C(O)Ph, C(O)OR 10 (For example, C(O)O-CH3, C(O)O-CH2CH3), R8-C(O)-R 10 (For example, CH2C(O)CH3), C(O)H, C(O)-R 10 (e.g., C(O)-CH3, C(O)-CH2CH3, C(O)-CH2CH2CH3), C1-C5 linear or branched C(O)-haloalkyl (e.g., C(O)-CF3), -C(O)NH2, C(O)NHR, C(O)N(R) 10 )(R 11 )(For example, C(O)N(CH3)2), SO2R, SO2N(R 10 )(R 11 )(e.g., SO2N(CH3)2), C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, C(OH)(CH3)(Ph), ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl), C1-C5 linear or branched, or C3-C8 cyclic haloalkyl (e.g., CF3, CF2CH3, CF2-cyclobutyl, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2), C1-C5 linear or branched, or C3-C8 cyclic alkoxy (e.g., methoxy, ethoxy, propoxy, isopropoxy, O-CH2-cyclopropyl), C 1-C5 linear or branched thiooxy, C1-C5 linear or branched haloalkoxy, C1-C5 linear or branched alkoxyalkyl, substituted or unsubstituted C3-C8 cycloalkyl (e.g., cyclopropyl, cyclopentyl), substituted or unsubstituted C3-C8 heterocyclic ring (e.g., 3-methyl-4H-1,2,4-triazole, 5-methyl-1,2,4-oxadiazole, thiophene, oxazole, isoxazole, imidazole, furan, triazole, pyridine (2,3, or 4-pyridine), pyrimidine, pyrazine, oxacyclobutane (1 or 2-oxacyclobutane), indole), substituted or unsubstituted aryl (e.g., phenyl), Alternatively, R3 and R4 may link together to form ring A as defined above (e.g., cyclopropyl, 5-methyloxazolidine-2-one), R5 is H, C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, CH2SH, ethyl, butyl, CH2-CCH, isopropyl, CH2-C(O)-OCH3), C2-C5 linear or branched, substituted or unsubstituted alkenyl, C2-C5 linear or branched, substituted or unsubstituted alkynyl (e.g., CCH, CH2-CCH), C1-C5 linear or branched haloalkyl (e.g., CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2), R8-aryl (e.g., CH2-Ph), C(=CH2)-R 10 (For example, C(=CH2)-C(O)-OCH3, C(=CH2)-CN), substituted or unsubstituted alkyl sulfones (for example, SO2-CH2-cyclopentyl), substituted or unsubstituted aryl compounds (for example, phenyl), substituted or unsubstituted heteroaryl compounds (for example, pyridine (2,3, and 4-pyridine)), R8 is [CH2] p And, p is between 1 and 10. R9, [CH] q [C] q And, q is between 2 and 10, R 10 and R 11 However, each is independently H, CN, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH3)), or S(O)2R, Or R 10 and R 11 However, they link together to form substituted or unsubstituted C3-C8 heterocyclic rings (e.g., piperazine, piperidine), R is H, a C1-C5 linear or branched alkyl (e.g., methyl, ethyl), a C1-C5 linear or branched alkoxy (e.g., methoxy), a phenyl, an aryl, or a heteroaryl, or two gem R substituents are linked together to form a 5 or 6-membered heterocyclic ring. m is an integer between 1 and 5 (for example, 1 or 2), n is an integer between 0 and 5 (for example, 0, 1, 2, or 3), X1 is S, O, N-OH, CH2, C(R)2, or N-OMe. Is X2 S, O, N-OH, CH2, C(R)2, or N-OMe? Alternatively, X2 may link with the adjacent carbon of X1 to form ring B represented by the following structure (in which case X1 is X7),

[0058] [ka]

[0059] If X4, X5, X6, and X7 are each independently C or N, and any of X4, X5, X6, and X7 is N, then each substitution R 90 , R 60 , R 70 , or R 80 It does not exist, R 60 , R 80 , and R 90 However, each is independent of H, F, Cl, Br, I, OH, SH, R8-OH, R8-SH, -R8-OR 10 , CF3, CN, NO2, NH2, NHR, N(R)2, R8-N(R 10 )(R 11 ), -OC(O)CF3, -OCH2Ph, NHC(O)OBz, -NHC(O)-R 10 COOH, -C(O)Ph, C(O)OR 10 C(O)H, C(O)-R 10 , C1-C5 linear or branched C(O)-haloalkyl, -C(O)NH2, C(O)NHR, C(O)N(R 10 )(R11 ), SO2R, SO2N(R 10 )(R 11 ), selected from C1-C5 linear or branched saturated or unsaturated alkyl, C1-C5 linear or branched, or C3-C8 cyclic haloalkyl, C1-C5 linear or branched, or C3-C8 cyclic alkoxy, C1-C5 linear or branched thioalkoxy, C1-C5 linear or branched haloalkoxy, C1-C5 linear or branched alkoxyalkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C3-C8 heterocyclic ring, substituted or unsubstituted aryl, R 70 However, H, F, Cl, Br, I, OH, SH, R8-OH, R8-SH, -R8-OR 10 , CF3, CN, NO2, NH2, NHR, N(R)2, R8-N(R 10 )(R 11 ), -OC(O)CF3, -OCH2Ph, NHC(O)OBz, -NHC(O)-R 10 COOH, -C(O)Ph, C(O)OR 10 C(O)H, C(O)-R 10 , C1-C5 linear or branched C(O)-haloalkyl, -C(O)NH2, C(O)NHR, C(O)N(R 10 )(R 11 ), SO2R, SO2N(R 10 )(R 11 ), selected from C1-C5 linear or branched, or C3-C8 cyclic haloalkyl, C1-C5 linear or branched, or C3-C8 cyclic alkoxy, C1-C5 linear or branched thioalkoxy, C1-C5 linear or branched haloalkoxy, C1-C5 linear or branched alkoxyalkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C3-C8 heterocyclic ring, substituted or unsubstituted aryl, X3 is O, NH, or NR 50 And, R 50However, this relates to compounds that are H, or C1-C5 linear or branched, substituted or unsubstituted alkyl groups, or their pesticide-acceptable salts, stereoisomers, tautomers, hydrates, N-oxides, reverse amide analogs, isotopic variants (e.g., deuterated analogs), or any combination thereof.

[0060] In some embodiments, R3 and R4 are linked together to form ring A. In some embodiments, ring B is absent. In some embodiments, B is pyridine. In some embodiments, R3 is OH or NH2. In some embodiments, R4 is NH2 or OH. In some embodiments, both R3 and R4 cannot be NH2. In some embodiments, if R3 is OH, then R4 is NH2. In some embodiments, if R3 is NH2, then R4 is OH. In some embodiments, if R3 is OH, then R4 is NH2, and if R3 is NH2, then R4 is OH. In some embodiments, if R3 is OH and R4 is NH2, then n+m cannot be equal to 3. In some embodiments, the compound is compound 101, 102, 104, 105, 106, 113, 114, 115, 116, 117, 118, 119, or 120, each representing a distinct embodiment according to the present invention. In some embodiments, ring A has two chiral centers. In some embodiments, the compound is not (6R,7S)-6-amino-7-hydroxyoctanoic acid. In some embodiments, the compound is not 5-((4R,5S)-5-methyl-2-oxoxazolidine-4-yl)pentanoic acid. In some embodiments, the compound is substantially a pure single stereoisomer. In some embodiments, R1, R1', R2, R2', and R 40Each is independently H, or a C1-C5 linear or branched substituted or unsubstituted alkyl (e.g., methyl, ethyl). In some embodiments, R1 and R1' are both H. In some embodiments, R2 is CH3 or CH2CH3. In some embodiments, R2' is H or CH3. In some embodiments, R 40 R5 is CH3 or H. In some embodiments, X1 is CH2. In some embodiments, X2 is CH2. In some embodiments, X3 is O, NH, or N-CH3. In some embodiments, R5 is H, or a C1-C5 linear or branched substituted or unsubstituted alkyl, or a substituted or unsubstituted alkyl sulfone. In some embodiments, R5 is a substituted or unsubstituted alkyl. In some embodiments, R5 is H. In some embodiments, R5 is H, ethyl, butyl, CH2-CCH, CH2-C(O)-OCH3, or SO2-CH2-cyclopentyl, each being a separate embodiment of the present invention. In some embodiments, n is 0, 1, 2, or 3. In some embodiments, n is 1. In some embodiments, m is 1 or 2. In some embodiments, m is 1.

[0061] In some embodiments, substitutions include F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl (e.g., imidazole), C3-C8 cycloalkyl (e.g., cyclohexyl), CN, NO2, or any combination thereof.

[0062] In some embodiments, the compound is one of the compounds listed in Table 1. In various embodiments, the compound is a herbicide compound. In various embodiments, the compound is intended for use in controlling undesirable plant growth. In some embodiments, the compound is one of the compounds listed in Table 2.

[0063] In various embodiments, the present invention relates to a compound represented by the structure of formula I(b),

[0064] [ka]

[0065] During the ceremony, C A and C B However, both are chiral carbon centers, or C A and C B However, together with R3 and R4, they form ring A represented by the following structure,

[0066] [ka]

[0067] R1, R1', R2, R2', and R 40 However, each is independently H, F, Cl, Br, I, OH, C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl, benzyl), or C(O)-R 10 (For example, C(O)-CH3, R3 is OH, F, SH, R8-OH (e.g., CH2-OH), NH2, NHNH2, NHR, N(R)2, NHC(O)OBz, -NHC(O)-R 10(For example, NHC(O)CH3), C1-C5 linear or branched, substituted or unsubstituted alkyl (for example, methyl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl), substituted or unsubstituted C3-C8 cycloalkyl, C1-C5 linear or branched, or C3-C8 cyclic haloalkyl, C1-C5 linear or branched, or C3-C8 cyclic alkoxy, substituted or unsubstituted C3-C8 heterocyclic ring, or unsubstituted or unsubstituted aryl, Alternatively, R3 and R2 may link together to form a C3-C8 substituted or unsubstituted, carbocyclic or heterocyclic ring (e.g., cyclopropyl). R4 is NH2, OH, NHNH2, NHR, N(R)2, -NHC(O)-R 10 , NHC(O)H, NHC(O)CH3, C1-C5 linear or branched, substituted or unsubstituted alkyl, C1-C5 linear or branched, or C3-C8 cyclic haloalkyl, C1-C5 linear or branched, or C3-C8 cyclic alkoxy, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C3-C8 heterocyclic ring, or substituted or unsubstituted aryl, Alternatively, R3 and R4 may link together to form the above-mentioned ring A (e.g., cyclopropyl, 5-methyloxazolidine-2-one[1,3]dioxol, furan-2(3H)-one, benzene, cyclopentane, imidazole), R5 is H, C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, CH2SH, ethyl, butyl, CH2-CCH, isopropyl, CH2-C(O)-OCH3), C2-C5 linear or branched, substituted or unsubstituted alkenyl, C2-C5 linear or branched, substituted or unsubstituted alkynyl (e.g., CCH, CH2-CCH), C1-C5 linear or branched haloalkyl (e.g., CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2), R8-aryl (e.g., CH2-Ph), C(=CH2)-R 10(For example, C(=CH2)-C(O)-OCH3, C(=CH2)-CN), substituted or unsubstituted alkyl sulfones (for example, SO2-CH2-cyclopentyl), substituted or unsubstituted aryl compounds (for example, phenyl), substituted or unsubstituted heteroaryl compounds (for example, pyridine (2,3, and 4-pyridine)), R8 is [CH2] p And, p is between 1 and 10. R 10 and R 11 However, each is independently H, CN, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH3)), or S(O)2R, Or R 10 and R 11 However, they link together to form substituted or unsubstituted C3-C8 heterocyclic rings (e.g., piperazine, piperidine), R is H, a C1-C5 linear or branched alkyl (e.g., methyl, ethyl), a C1-C5 linear or branched alkoxy (e.g., methoxy), a phenyl, an aryl, or a heteroaryl, or two gem R substituents are linked together to form a 5 or 6-membered heterocyclic ring. m is an integer between 1 and 5 (for example, 1 or 2), n is an integer between 0 and 5 (for example, 0, 1, 2, or 3), X1 is S, O, or CH2, Is X2 S, O, or CH2? Alternatively, X2 may link with the adjacent carbon of X1 to form ring B represented by the following structure (in which case X1 is X7),

[0068] [ka]

[0069] If X4, X5, X6, and X7 are each independently C or N, and any of X4, X5, X6, and X7 is N, then each substitution R 90 , R 60 , R70 , or R 80 It does not exist, R 60 , R 80 , and R 90 However, each is independent of H, F, Cl, Br, I, OH, SH, R8-OH, R8-SH, -R8-OR 10 , CF3, CN, NO2, NH2, NHR, N(R)2, R8-N(R 10 )(R 11 ), -OC(O)CF3, -OCH2Ph, NHC(O)OBz, -NHC(O)-R 10 COOH, -C(O)Ph, C(O)OR 10 C(O)H, C(O)-R 10 , C1-C5 linear or branched C(O)-haloalkyl, -C(O)NH2, C(O)NHR, C(O)N(R 10 )(R 11 ), SO2R, SO2N(R 10 )(R 11 ), selected from C1-C5 linear or branched saturated or unsaturated alkyl, C1-C5 linear or branched, or C3-C8 cyclic haloalkyl, C1-C5 linear or branched, or C3-C8 cyclic alkoxy, C1-C5 linear or branched thioalkoxy, C1-C5 linear or branched haloalkoxy, C1-C5 linear or branched alkoxyalkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C3-C8 heterocyclic ring, substituted or unsubstituted aryl, R 70 However, H, F, Cl, Br, I, OH, SH, R8-OH, R8-SH, -R8-OR 10 , CF3, CN, NO2, NH2, NHR, N(R)2, R8-N(R 10 )(R 11 ), -OC(O)CF3, -OCH2Ph, NHC(O)OBz, -NHC(O)-R 10 COOH, -C(O)Ph, C(O)OR 10 C(O)H, C(O)-R 10 , C1-C5 linear or branched C(O)-haloalkyl, -C(O)NH2, C(O)NHR, C(O)N(R 10 )(R 11 ), SO2R, SO2N(R10 )(R 11 ), selected from C1-C5 linear or branched, or C3-C8 cyclic haloalkyl, C1-C5 linear or branched, or C3-C8 cyclic alkoxy, C1-C5 linear or branched thioalkoxy, C1-C5 linear or branched haloalkoxy, C1-C5 linear or branched alkoxyalkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C3-C8 heterocyclic ring, substituted or unsubstituted aryl, X3 is O, NH, or NR 50 And, R 50 However, this relates to compounds that are H, or C1-C5 linear or branched, substituted or unsubstituted alkyl groups, or their pesticide-acceptable salts, stereoisomers, tautomers, hydrates, N-oxides, reverse amide analogs, isotopic variants (e.g., deuterated analogs), or any combination thereof.

[0070] In some embodiments, R3 and R4 are linked together to form ring A. In some embodiments, ring B is absent. In some embodiments, B is pyridine. In some embodiments, R3 is OH or NH2. In some embodiments, R4 is NH2 or OH. In some embodiments, both R3 and R4 cannot be NH2. In some embodiments, if R3 is OH, then R4 is NH2. In some embodiments, if R3 is NH2, then R4 is OH. In some embodiments, if R3 is OH, then R4 is NH2, and if R3 is NH2, then R4 is OH. In some embodiments, if R3 is OH and R4 is NH2, then n+m cannot be equal to 3. In some embodiments, the compound is compound 101, 102, 104, 105, 106, 113, 114, 115, 116, 117, 118, 119, or 120, each representing a distinct embodiment according to the present invention. In some embodiments, ring A has two chiral centers. In some embodiments, the compound is not (6R,7S)-6-amino-7-hydroxyoctanoic acid. In some embodiments, the compound is not 5-((4R,5S)-5-methyl-2-oxoxazolidine-4-yl)pentanoic acid. In some embodiments, the compound is substantially a pure single stereoisomer. In some embodiments, R1, R1', R2, R2', and R 40 Each is independently H, or a C1-C5 linear or branched substituted or unsubstituted alkyl (e.g., methyl, ethyl). In some embodiments, R1 and R1' are both H. In some embodiments, R2 is CH3 or CH2CH3. In some embodiments, R2' is H or CH3. In some embodiments, R 40R5 is CH3 or H. In some embodiments, X1 is CH2. In some embodiments, X2 is CH2. In some embodiments, X3 is O, NH, or N-CH3. In some embodiments, R5 is H, or a C1-C5 linear or branched substituted or unsubstituted alkyl, or a substituted or unsubstituted alkyl sulfone. In some embodiments, R5 is a substituted or unsubstituted alkyl. In some embodiments, R5 is H. In some embodiments, R5 is H, ethyl, butyl, CH2-CCH, CH2-C(O)-OCH3, or SO2-CH2-cyclopentyl, each being a separate embodiment of the present invention. In some embodiments, n is 0, 1, 2, or 3. In some embodiments, n is 1. In some embodiments, m is 1 or 2. In some embodiments, m is 1.

[0071] In some embodiments, substitutions include, but are not limited to, F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl (e.g., imidazole), C3-C8 cycloalkyl (e.g., cyclohexyl), CN, NO2, or any combination thereof.

[0072] In some embodiments, the compound is one of the compounds listed in Table 1. In various embodiments, the compound is a herbicide compound. In various embodiments, the compound is intended for use in controlling undesirable plant growth. In some embodiments, the compound is one of the compounds listed in Table 2.

[0073] In various embodiments, the present invention relates to a compound represented by the structure of formula I(c),

[0074] [ka]

[0075] During the ceremony, C A and C B However, both are chiral carbon centers, R1, R1', R2, R2', and R 40 However, each is independently H, F, Cl, Br, I, OH, C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl, benzyl), or C(O)-R 10 (For example, C(O)-CH3, R3 is OH, F, R8-OH (e.g., CH2-OH), SH, NH2, NHNH2, NHR, N(R)2, NHC(O)OBz, -NHC(O)-R 10 (For example, NHC(O)CH3), C1-C5 linear or branched, substituted or unsubstituted alkyl (for example, methyl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl), substituted or unsubstituted C3-C8 cycloalkyl, C1-C5 linear or branched, or C3-C8 cyclic haloalkyl, C1-C5 linear or branched, or C3-C8 cyclic alkoxy, substituted or unsubstituted C3-C8 heterocyclic ring, or unsubstituted or unsubstituted aryl, Alternatively, R3 and R2 may link together to form a C3-C8 substituted or unsubstituted, carbocyclic or heterocyclic ring (e.g., cyclopropyl). R4 is OH, NH2, NHNH2, NHR, N(R)2, -NHC(O)-R 10, NHC(O)H, NHC(O)CH3, C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, C(OH)(CH3)(Ph), ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl), C1-C5 linear or branched, or C3-C8 cyclic haloalkyl, C1-C5 linear or branched, or C3-C8 cyclic alkoxy, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C3-C8 heterocyclic ring, or substituted or unsubstituted alkyl, R5 is H, C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, CH2SH, ethyl, butyl, CH2-CCH, isopropyl, CH2-C(O)-OCH3), C2-C5 linear or branched, substituted or unsubstituted alkenyl, C2-C5 linear or branched, substituted or unsubstituted alkynyl (e.g., CCH, CH2-CCH), C1-C5 linear or branched haloalkyl (e.g., CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2), R8-aryl (e.g., CH2-Ph), C(=CH2)-R 10 (For example, C(=CH2)-C(O)-OCH3, C(=CH2)-CN), substituted or unsubstituted alkyl sulfones (for example, SO2-CH2-cyclopentyl), substituted or unsubstituted aryl compounds (for example, phenyl), substituted or unsubstituted heteroaryl compounds (for example, pyridine (2,3, and 4-pyridine)), R8 is [CH2] p And, p is between 1 and 10. R 10 and R 11 However, each is independently H, CN, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH3)), or S(O)2R, Or R 10 and R 11 However, they link together to form substituted or unsubstituted C3-C8 heterocyclic rings (e.g., piperazine, piperidine), R is H, C1-C5 linear or branched alkyl, C1-C5 linear or branched alkoxy, phenyl, aryl, or heteroaryl, or two gem R substituents are linked together to form a 5 or 6-membered heterocyclic ring. m is an integer between 1 and 5 (for example, 1 or 2), n is an integer between 0 and 5 (for example, 0, 1, 2, or 3), X1 is S, O, N-OH, CH2, C(R)2, or N-OMe. X2 is S, O, N-OH, CH2, C(R)2, or N-OMe. X3 is O, NH, or NR 50 And, R 50 However, this relates to compounds that are H, or C1-C5 linear or branched, substituted or unsubstituted alkyl groups, or their pesticide-acceptable salts, stereoisomers, tautomers, hydrates, N-oxides, reverse amide analogs, isotopic variants (e.g., deuterated analogs), or any combination thereof.

[0076] In some embodiments, R3 is OH or NH2. In some embodiments, R4 is NH2 or OH. In some embodiments, both R3 and R4 cannot be NH2. In some embodiments, if R3 is OH, then R4 is NH2. In some embodiments, if R3 is NH2, then R4 is OH. In some embodiments, if R3 is OH, then R4 is NH2, and if R3 is NH2, then R4 is OH. In some embodiments, if R3 is OH and R4 is NH2, then n+m cannot be equal to 3. In some embodiments, the compound is compound 101, 102, 104, 105, 106, 113, 114, 115, 116, 117, 118, 119, or 120, each representing a distinct embodiment according to the present invention. In some embodiments, the compound is not (6R,7S)-6-amino-7-hydroxyoctanoic acid. In some embodiments, the compound is substantially a pure single stereoisomer. In some embodiments, R1, R1', R2, R2', and R 40 Each is independently H, or a C1-C5 linear or branched substituted or unsubstituted alkyl (e.g., methyl, ethyl). In some embodiments, R1 and R1' are both H. In some embodiments, R2 is CH3 or CH2CH3. In some embodiments, R2' is H or CH3. In some embodiments, R 40R5 is CH3 or H. In some embodiments, X1 is CH2. In some embodiments, X2 is CH2. In some embodiments, X3 is O, NH, or N-CH3. In some embodiments, R5 is H, or a C1-C5 linear or branched substituted or unsubstituted alkyl, or a substituted or unsubstituted alkyl sulfone. In some embodiments, R5 is a substituted or unsubstituted alkyl. In some embodiments, R5 is H. In some embodiments, R5 is H, ethyl, butyl, CH2-CCH, CH2-C(O)-OCH3, or SO2-CH2-cyclopentyl, each being a separate embodiment of the present invention. In some embodiments, n is 0, 1, 2, or 3. In some embodiments, n is 1. In some embodiments, m is 1 or 2. In some embodiments, m is 1.

[0077] In some embodiments, substitutions include, but are not limited to, F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl (e.g., imidazole), C3-C8 cycloalkyl (e.g., cyclohexyl), CN, NO2, or any combination thereof.

[0078] In various embodiments, the compound is a herbicide compound. In various embodiments, the compound is intended for use in controlling the growth of undesirable plants.

[0079] In various embodiments, the present invention relates to a compound represented by the structure of formula I(d),

[0080] [ka]

[0081] During the ceremony, R1, R1', R2, and R2' are each independently H, C1-C5 linear or branched substituted or unsubstituted alkyl groups (e.g., methyl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl, benzyl), or C(O)-R 10 (For example, C(O)-CH3, R5 is H, C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, CH2SH, ethyl, butyl, CH2-CCH, isopropyl, CH2-C(O)-OCH3), C2-C5 linear or branched, substituted or unsubstituted alkenyl, C2-C5 linear or branched, substituted or unsubstituted alkynyl (e.g., CCH, CH2-CCH), C1-C5 linear or branched haloalkyl (e.g., CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2), R8-aryl (e.g., CH2-Ph), C(=CH2)-R 10 (For example, C(=CH2)-C(O)-OCH3, C(=CH2)-CN), substituted or unsubstituted alkyl sulfones (for example, SO2-CH2-cyclopentyl), substituted or unsubstituted aryl compounds (for example, phenyl), substituted or unsubstituted heteroaryl compounds (for example, pyridine (2,3, and 4-pyridine)), R 10 However, it is H, CN, C1-C5 linear or branched alkyl, C(O)R, or S(O)2R. R is H, C1-C5 linear or branched alkyl, C1-C5 linear or branched alkoxy, phenyl, aryl, or heteroaryl, or two gem R substituents are linked together to form a 5 or 6-membered heterocyclic ring. m is an integer between 1 and 5 (for example, 1 or 2), n is an integer between 0 and 5 (for example, 0, 1, 2, or 3), X1 is S, O, N-OH, CH2, C(R)2, or N-OMe. Is X2 S, O, N-OH, CH2, C(R)2, or N-OMe? Alternatively, X2 may link with the adjacent carbon of X1 to form ring B represented by the following structure (in which case X1 is X7),

[0082] [ka]

[0083] If X4, X5, X6, and X7 are each independently C or N, and any of X4, X5, X6, and X7 is N, then each substitution R 90 , R 60 , R 70 , or R 80 It does not exist, R 60 , R 70 , R 80 , and R 90 However, each is independent of H, F, Cl, Br, I, OH, SH, R8-OH, R8-SH, -R8-OR 10 , CF3, CN, NO2, NH2, NHR, N(R)2, R8-N(R 10 )(R 11 ), -OC(O)CF3, -OCH2Ph, NHC(O)OBz, -NHC(O)-R 10 COOH, -C(O)Ph, C(O)OR 10 C(O)H, C(O)-R 10 , C1-C5 linear or branched C(O)-haloalkyl, -C(O)NH2, C(O)NHR, C(O)N(R 10 )(R 11 ), SO2R, SO2N(R 10 )(R 11), selected from C1-C5 linear or branched saturated or unsaturated alkyl, C1-C5 linear or branched, or C3-C8 cyclic haloalkyl, C1-C5 linear or branched, or C3-C8 cyclic alkoxy, C1-C5 linear or branched thioalkoxy, C1-C5 linear or branched haloalkoxy, C1-C5 linear or branched alkoxyalkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C3-C8 heterocyclic ring, substituted or unsubstituted aryl, X3 is O, NH, or NR 50 And, R 50 However, this relates to compounds that are H, or C1-C5 linear or branched, substituted or unsubstituted alkyl groups, or their pesticide-acceptable salts, stereoisomers, tautomers, hydrates, N-oxides, reverse amide analogs, isotopic variants (e.g., deuterated analogs), or any combination thereof.

[0084] In some embodiments, the compound is not 5-((4R,5S)-5-methyl-2-oxoxazolidine-4-yl)pentanoic acid. In some embodiments, the compound is substantially a pure single stereoisomer. In some embodiments, R1, R1', R2, R2', and R 40 Each is independently H, or a C1-C5 linear or branched substituted or unsubstituted alkyl (e.g., methyl, ethyl). In some embodiments, R1 and R1' are both H. In some embodiments, R2 is CH3 or CH2CH3. In some embodiments, R2' is H or CH3. In some embodiments, R 40R5 is CH3 or H. In some embodiments, X1 is CH2. In some embodiments, X2 is CH2. In some embodiments, X3 is O, NH, or N-CH3. In some embodiments, R5 is H, or a C1-C5 linear or branched substituted or unsubstituted alkyl, or a substituted or unsubstituted alkyl sulfone. In some embodiments, R5 is a substituted or unsubstituted alkyl. In some embodiments, R5 is H. In some embodiments, R5 is H, ethyl, butyl, CH2-CCH, CH2-C(O)-OCH3, or SO2-CH2-cyclopentyl, each representing a separate embodiment of the present invention. In some embodiments, n is 0, 1, 2, or 3. In some embodiments, n is 1. In some embodiments, m is 1 or 2. In some embodiments, m is 1. In some embodiments, the compounds are compounds 105 and 106, each representing a separate embodiment of the present invention.

[0085] In some embodiments, substitutions include, but are not limited to, F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl (e.g., imidazole), C3-C8 cycloalkyl (e.g., cyclohexyl), CN, NO2, or any combination thereof.

[0086] In various embodiments, the compound is a herbicide compound. In various embodiments, the compound is intended for use in controlling the growth of undesirable plants.

[0087] In various embodiments, the present invention relates to a compound represented by the structure of formula I(e),

[0088] [ka]

[0089] During the ceremony, R1, R1', R2, and R2' are each independently H, F, Cl, Br, I, OH, C1-C5 linear or branched substituted or unsubstituted alkyl groups (e.g., methyl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl, benzyl), or C(O)-R 10 (For example, C(O)-CH3, R3 is OH, F, SH, R8-OH (e.g., CH2-OH), NH2, NHNH2, NHR, N(R)2, NHC(O)OBz, -NHC(O)-R 10 (For example, NHC(O)CH3), C1-C5 linear or branched, substituted or unsubstituted alkyl (for example, methyl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl), substituted or unsubstituted C3-C8 cycloalkyl, C1-C5 linear or branched, or C3-C8 cyclic haloalkyl, C1-C5 linear or branched, or C3-C8 cyclic alkoxy, substituted or unsubstituted C3-C8 heterocyclic ring, or unsubstituted or unsubstituted aryl, R4 is NH2, OH, NHNH2, NHR, N(R)2, -NHC(O)-R 10 , NHC(O)H, NHC(O)CH3, C1-C5 linear or branched, substituted or unsubstituted alkyl, C1-C5 linear or branched, or C3-C8 cyclic haloalkyl, C1-C5 linear or branched, or C3-C8 cyclic alkoxy, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C3-C8 heterocyclic ring, or substituted or unsubstituted aryl, Alternatively, R3 and R4 may link together to form a 5 or 6-membered substituted or unsubstituted, aliphatic or aromatic, carbocyclic or heterocyclic ring (e.g., cyclopropyl, 5-methyloxazolidine-2-one[1,3]dioxol, furan-2(3H)-one, benzene, cyclopentane, imidazole), R5 is H, C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, CH2SH, ethyl, butyl, CH2-CCH, isopropyl, CH2-C(O)-OCH3), C2-C5 linear or branched, substituted or unsubstituted alkenyl, C2-C5 linear or branched, substituted or unsubstituted alkynyl (e.g., CCH, CH2-CCH), C1-C5 linear or branched haloalkyl (e.g., CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2), R8-aryl (e.g., CH2-Ph), C(=CH2)-R 10 (For example, C(=CH2)-C(O)-OCH3, C(=CH2)-CN), substituted or unsubstituted alkyl sulfones (for example, SO2-CH2-cyclopentyl), substituted or unsubstituted aryl compounds (for example, phenyl), substituted or unsubstituted heteroaryl compounds (for example, pyridine (2,3, and 4-pyridine)), R8 is [CH2] p And, p is between 1 and 10. R 10 and R 11 However, each is independently H, CN, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH3)), or S(O)2R, Or R 10 and R 11 However, they link together to form substituted or unsubstituted C3-C8 heterocyclic rings (e.g., piperazine, piperidine), R is H, C1-C5 linear or branched alkyl, C1-C5 linear or branched alkoxy, phenyl, aryl, or heteroaryl, or two gem R substituents are linked together to form a 5 or 6-membered heterocyclic ring. n is 0, 1, 2, or 3, R 60 , R 70 , R 80 , and R 90 However, each is independent of H, F, Cl, Br, I, OH, SH, R8-OH, R8-SH, -R8-OR 10, CF3, CN, NO2, NH2, NHR, N(R)2, R8-N(R 10 )(R 11 ), -OC(O)CF3, -OCH2Ph, NHC(O)OBz, -NHC(O)-R 10 COOH, -C(O)Ph, C(O)OR 10 C(O)H, C(O)-R 10 , C1-C5 linear or branched C(O)-haloalkyl, -C(O)NH2, C(O)NHR, C(O)N(R 10 )(R 11 ), SO2R, SO2N(R 10 )(R 11 ), selected from C1-C5 linear or branched substituted or unsubstituted alkyl, C1-C5 linear or branched, or C3-C8 cyclic haloalkyl, C1-C5 linear or branched, or C3-C8 cyclic alkoxy, C1-C5 linear or branched thioalkoxy, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C3-C8 heterocyclic ring, substituted or unsubstituted aryl, X3 is O, NH, or NR 50 And, R 50 However, H, or a C1-C5 linear or branched, substituted or unsubstituted alkyl, If X4, X5, X6, and X7 are each independently C or N, and any of X4, X5, X6, and X7 is N, then each substitution R 90 , R 60 , R 70 , or R 80 However, it does not exist. This relates to compounds, or their pesticide-permissible salts, stereoisomers, tautomers, hydrates, N-oxides, reverse amide analogs, isotopic variants (e.g., deuterated analogs), or any combination thereof.

[0090] In some embodiments, if R4 is NH2, then R3 cannot be OH. In some embodiments, if R3 is OH and R4 is NH2, then n cannot be 1. In some embodiments, if R3 is OH and R4 is NH2, then X7-R 90 It cannot be CH.

[0091] In some embodiments, substitutions include, but are not limited to, F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl (e.g., imidazole), C3-C8 cycloalkyl (e.g., cyclohexyl), CN, NO2, or any combination thereof.

[0092] In various embodiments, the compound is a herbicide compound. In various embodiments, the compound is intended for use in controlling the growth of undesirable plants. In some embodiments, the compound is compound 108, 109, 141, 142, 172, 173, 174, 175, 176, 177, or 178, each representing a distinct embodiment according to the present invention.

[0093] In various embodiments, the present invention relates to a compound represented by the structure of formula I(f),

[0094] [ka]

[0095] R1, R1', R2, and R2' are each independently H, F, Cl, Br, I, OH, C1-C5 linear or branched substituted or unsubstituted alkyl groups (e.g., methyl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl, benzyl), or C(O)-R 10 (For example, C(O)-CH3, R3 is SH, NHNH2, or NHC(O)OBz. R4 is NH2, OH, NHNH2, =NH-OH, =O, =N-NH2, NHR, N(R)2, -NHC(O)-R 10 , NHC(O)H, NHC(O)CH3, C1-C5 linear or branched, substituted or unsubstituted alkyl, C1-C5 linear or branched, or C3-C8 cyclic haloalkyl, C1-C5 linear or branched, or C3-C8 cyclic alkoxy, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C3-C8 heterocyclic ring, or substituted or unsubstituted aryl, R5 is H, C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, CH2SH, ethyl, butyl, CH2-CCH, isopropyl, CH2-C(O)-OCH3), C2-C5 linear or branched, substituted or unsubstituted alkenyl, C2-C5 linear or branched, substituted or unsubstituted alkynyl (e.g., CCH, CH2-CCH), C1-C5 linear or branched haloalkyl (e.g., CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2), R8-aryl (e.g., CH2-Ph), C(=CH2)-R 10 (For example, C(=CH2)-C(O)-OCH3, C(=CH2)-CN), substituted or unsubstituted alkyl sulfones (for example, SO2-CH2-cyclopentyl), substituted or unsubstituted aryl compounds (for example, phenyl), substituted or unsubstituted heteroaryl compounds (for example, pyridine (2,3, and 4-pyridine)), R8 is [CH2] p And, p is between 1 and 10. R 10 and R 11However, each is independently H, CN, C1-C5 linear or branched alkyl, C(O)R, or S(O)2R, Or R 10 and R 11 However, they are linked together to form a substituted or unsubstituted C3-C8 heterocycle. R is H, C1-C5 linear or branched alkyl, C1-C5 linear or branched alkoxy, phenyl, aryl, or heteroaryl, or two gem R substituents are linked together to form a 5 or 6-membered heterocyclic ring. m is an integer between 1 and 5 (for example, 1 or 2), n is an integer between 0 and 5 (for example, 0, 1, 2, or 3), X1 is S, O, N-OH, CH2, C(R)2, or N-OMe. Is X2 S, O, N-OH, CH2, C(R)2, or N-OMe? Alternatively, X2 may link with the adjacent carbon of X1 to form ring B represented by the following structure (in which case X1 is X7),

[0096] [ka]

[0097] If X4, X5, X6, and X7 are each independently C or N, and any of X4, X5, X6, and X7 is N, then each substitution R 90 , R 60 , R 70 , or R 80 However, it does not exist. R 60 , R 70 , R 80 , and R 90 However, each is independent of H, F, Cl, Br, I, OH, SH, R8-OH, R8-SH, -R8-OR 10 , CF3, CN, NO2, NH2, NHR, N(R)2, R8-N(R 10 )(R 11 ), -OC(O)CF3, -OCH2Ph, NHC(O)OBz, -NHC(O)-R 10COOH, -C(O)Ph, C(O)OR 10 C(O)H, C(O)-R 10 , C1-C5 linear or branched C(O)-haloalkyl, -C(O)NH2, C(O)NHR, C(O)N(R 10 )(R 11 ), SO2R, SO2N(R 10 )(R 11 ), selected from C1-C5 linear or branched saturated or unsaturated alkyl, C1-C5 linear or branched, or C3-C8 cyclic haloalkyl, C1-C5 linear or branched, or C3-C8 cyclic alkoxy, C1-C5 linear or branched thioalkoxy, C1-C5 linear or branched haloalkoxy, C1-C5 linear or branched alkoxyalkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C3-C8 heterocyclic ring, substituted or unsubstituted aryl, X3 is O, NH, or NR 50 And, R 50 However, this relates to compounds that are H, or C1-C5 linear or branched, substituted or unsubstituted alkyl groups, or their pesticide-acceptable salts, stereoisomers, tautomers, hydrates, N-oxides, reverse amide analogs, isotopic variants (e.g., deuterated analogs), or any combination thereof.

[0098] In some embodiments, substitutions include, but are not limited to, F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl (e.g., imidazole), C3-C8 cycloalkyl (e.g., cyclohexyl), CN, NO2, or any combination thereof.

[0099] In various embodiments, the compound is a herbicide compound. In various embodiments, the compound is intended for use in controlling the growth of undesirable plants.

[0100] In various embodiments, the present invention relates to a compound represented by the structure of formula I(g),

[0101] [ka]

[0102] During the ceremony, R1, R1', R2, R2', and R 40 However, each is independently H, F, Cl, Br, I, OH, C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl, benzyl), or C(O)-R 10 (For example, C(O)-CH3, R3 is F, OH, SH, R8-OH (e.g., CH2-OH), NH2, NHNH2, NHR, N(R)2, NHC(O)OBz, -NHC(O)-R 10 (For example, NHC(O)CH3), C1-C5 linear or branched, substituted or unsubstituted alkyl (for example, methyl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl), substituted or unsubstituted C3-C8 cycloalkyl, C1-C5 linear or branched, or C3-C8 cyclic haloalkyl, C1-C5 linear or branched, or C3-C8 cyclic alkoxy, substituted or unsubstituted C3-C8 heterocyclic ring, or unsubstituted or unsubstituted aryl, R4 is OH, NH2, NHNH2, NHR, N(R)2, -NHC(O)-R 10 , NHC(O)H, NHC(O)CH3, C1-C5 linear or branched, substituted or unsubstituted alkyl, C1-C5 linear or branched, or C3-C8 cyclic haloalkyl, C1-C5 linear or branched, or C3-C8 cyclic alkoxy, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C3-C8 heterocyclic ring, or substituted or unsubstituted aryl, Alternatively, R3 and R4 may be linked together to form a ring A represented by the following structure,

[0103] [ka]

[0104] (For example, 5-methyloxazolidine-2-one) R5 is H, C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, CH2SH, ethyl, butyl, CH2-CCH, isopropyl, CH2-C(O)-OCH3), C2-C5 linear or branched, substituted or unsubstituted alkenyl, C2-C5 linear or branched, substituted or unsubstituted alkynyl (e.g., CCH, CH2-CCH), C1-C5 linear or branched haloalkyl (e.g., CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2), R8-aryl (e.g., CH2-Ph), C(=CH2)-R 10 (For example, C(=CH2)-C(O)-OCH3, C(=CH2)-CN), substituted or unsubstituted alkyl sulfones (for example, SO2-CH2-cyclopentyl), substituted or unsubstituted aryl compounds (for example, phenyl), substituted or unsubstituted heteroaryl compounds (for example, pyridine (2,3, and 4-pyridine)), R8 is [CH2] p And, p is between 1 and 10. R 10 and R 11 However, each is independently H, CN, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH3)), or S(O)2R, Or R 10 and R 11 However, they link together to form substituted or unsubstituted C3-C8 heterocyclic rings (e.g., piperazine, piperidine), R is H, C1-C5 linear or branched alkyl, C1-C5 linear or branched alkoxy, phenyl, aryl, or heteroaryl, or two gem R substituents are linked together to form a 5 or 6-membered heterocyclic ring. m is an integer between 1 and 5 (for example, 1 or 2), n is an integer between 0 and 5 (for example, 0, 1, 2, or 3), X1 is S, O, N-OH, CH2, C(R)2, or N-OMe. X2 is S, O, N-OH, CH2, C(R)2, or N-OMe. X3 is O, NH, or NR 50 And, R 50 However, this relates to compounds that are H, or C1-C5 linear or branched, substituted or unsubstituted alkyl groups, or their pesticide-acceptable salts, stereoisomers, tautomers, hydrates, N-oxides, reverse amide analogs, isotopic variants (e.g., deuterated analogs), or any combination thereof.

[0105] In various embodiments, R3 and R4 of the compound of formula I(g) cannot both be NH2. In various embodiments, if R3 is OH and R4 is NH2, then n+m cannot be equal to 3. In various embodiments, R3 is OH or NH2. In various embodiments, R4 is NH2 or OH. In some embodiments, if R3 is OH, then R4 is NH2. In some embodiments, if R3 is NH2, then R4 is OH. In various embodiments, if R3 is OH, then R4 is NH2, and if R3 is NH2, then R4 is OH. In some embodiments, the compound is compound 101, 102, 104, 105, 106, 113, 114, 115, 116, 117, 118, 119, or 120, each representing a distinct embodiment according to the present invention. In some embodiments, ring A has two chiral centers. In some embodiments, the compound is not (6R,7S)-6-amino-7-hydroxyoctanoic acid. In some embodiments, the compound is not 5-((4R,5S)-5-methyl-2-oxoxazolidine-4-yl)pentanoic acid. In some embodiments, the compound is substantially a pure single stereoisomer. In some embodiments, R1, R1', R2, R2', and R 40 Each is independently H, or a C1-C5 linear or branched substituted or unsubstituted alkyl (e.g., methyl, ethyl). In some embodiments, R1 and R1' are both H. In some embodiments, R2 is CH3 or CH2CH3. In some embodiments, R2' is H or CH3. In some embodiments, R 40R5 is CH3 or H. In some embodiments, X1 is CH2. In some embodiments, X2 is CH2. In some embodiments, X3 is O, NH, or N-CH3. In some embodiments, R5 is H, or a C1-C5 linear or branched substituted or unsubstituted alkyl, or a substituted or unsubstituted alkyl sulfone. In some embodiments, R5 is a substituted or unsubstituted alkyl. In some embodiments, R5 is H. In some embodiments, R5 is H, ethyl, butyl, CH2-CCH, CH2-C(O)-OCH3, or SO2-CH2-cyclopentyl, each being a separate embodiment of the present invention. In some embodiments, n is 0, 1, 2, or 3. In some embodiments, n is 1. In some embodiments, m is 1 or 2. In some embodiments, m is 1.

[0106] In some embodiments, substitutions include, but are not limited to, F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl (e.g., imidazole), C3-C8 cycloalkyl (e.g., cyclohexyl), CN, NO2, or any combination thereof.

[0107] In various embodiments, the compound is a herbicide compound. In various embodiments, the compound is intended for use in controlling the growth of undesirable plants.

[0108] In various embodiments, the present invention relates to a compound represented by the structure of formula I(ga),

[0109] [ka]

[0110] During the ceremony, C A and C B However, both are chiral carbon centers, or C A and C B However, together with R3 and R4, they form ring A represented by the following structure,

[0111] [ka]

[0112] (For example, 5-methyloxazolidine-2-one) R1, R1', R2, R2', and R 40 However, each is independently H, F, Cl, Br, I, OH, C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl, benzyl), or C(O)-R 10 (For example, C(O)-CH3, R3 is F, OH, SH, R8-OH (e.g., CH2-OH), NH2, NHNH2, NHR, N(R)2, NHC(O)OBz, -NHC(O)-R 10 (For example, NHC(O)CH3), C1-C5 linear or branched, substituted or unsubstituted alkyl (for example, methyl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl), substituted or unsubstituted C3-C8 cycloalkyl, C1-C5 linear or branched, or C3-C8 cyclic haloalkyl, C1-C5 linear or branched, or C3-C8 cyclic alkoxy, substituted or unsubstituted C3-C8 heterocyclic ring, or unsubstituted or unsubstituted aryl, R4 is OH, NH2, NHNH2, NHR, N(R)2, -NHC(O)-R 10, NHC(O)H, NHC(O)CH3, C1-C5 linear or branched, substituted or unsubstituted alkyl, C1-C5 linear or branched, or C3-C8 cyclic haloalkyl, C1-C5 linear or branched, or C3-C8 cyclic alkoxy, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C3-C8 heterocyclic ring, or substituted or unsubstituted aryl, R5 is H, C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, CH2SH, ethyl, butyl, CH2-CCH, isopropyl, CH2-C(O)-OCH3), C2-C5 linear or branched, substituted or unsubstituted alkenyl, C2-C5 linear or branched, substituted or unsubstituted alkynyl (e.g., CCH, CH2-CCH), C1-C5 linear or branched haloalkyl (e.g., CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2), R8-aryl (e.g., CH2-Ph), C(=CH2)-R 10 (For example, C(=CH2)-C(O)-OCH3, C(=CH2)-CN), substituted or unsubstituted alkyl sulfones (for example, SO2-CH2-cyclopentyl), substituted or unsubstituted aryl compounds (for example, phenyl), substituted or unsubstituted heteroaryl compounds (for example, pyridine (2,3, and 4-pyridine)), R8 is [CH2] p And, p is between 1 and 10. R 10 and R 11 However, each is independently H, CN, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH3)), or S(O)2R, Or R 10 and R 11 However, they link together to form substituted or unsubstituted C3-C8 heterocyclic rings (e.g., piperazine, piperidine), R is H, C1-C5 linear or branched alkyl, C1-C5 linear or branched alkoxy, phenyl, aryl, or heteroaryl, or two gem R substituents are linked together to form a 5 or 6-membered heterocyclic ring. m is an integer between 1 and 5 (for example, 1 or 2), n is an integer between 0 and 5 (for example, 0, 1, 2, or 3), X1 is S, O, N-OH, CH2, C(R)2, or N-OMe. X2 is S, O, N-OH, CH2, C(R)2, or N-OMe. X3 is O, NH, or NR 50 And, R 50 However, this relates to compounds that are H, or C1-C5 linear or branched, substituted or unsubstituted alkyl groups, or their pesticide-acceptable salts, stereoisomers, tautomers, hydrates, N-oxides, reverse amide analogs, isotopic variants (e.g., deuterated analogs), or any combination thereof.

[0113] In various embodiments, R3 and R4 of the compound of formula I(ga) cannot both be NH2. In various embodiments, if R3 is OH and R4 is NH2, then n+m cannot be equal to 3. In various embodiments, R3 is OH or NH2. In various embodiments, R4 is NH2 or OH. In various embodiments, if R3 is OH, then R4 is NH2, and if R3 is NH2, then R4 is OH. In some embodiments, if R3 is OH, then R4 is NH2. In some embodiments, if R3 is NH2, then R4 is OH. In some embodiments, the compound is compound 101, 102, 104, 105, 106, 113, 114, 115, 116, 117, 118, 119, or 120, each representing a distinct embodiment according to the present invention. In some embodiments, ring A has two chiral centers. In some embodiments, the compound is not (6R,7S)-6-amino-7-hydroxyoctanoic acid. In some embodiments, the compound is not 5-((4R,5S)-5-methyl-2-oxoxazolidine-4-yl)pentanoic acid. In some embodiments, the compound is substantially a pure single stereoisomer. In some embodiments, R1, R1', R2, R2', and R 40 Each is independently H, or a C1-C5 linear or branched substituted or unsubstituted alkyl (e.g., methyl, ethyl). In some embodiments, R1 and R1' are both H. In some embodiments, R2 is CH3 or CH2CH3. In some embodiments, R2' is H or CH3. In some embodiments, R 40R5 is CH3 or H. In some embodiments, X1 is CH2. In some embodiments, X2 is CH2. In some embodiments, X3 is O, NH, or N-CH3. In some embodiments, R5 is H, or a C1-C5 linear or branched substituted or unsubstituted alkyl, or a substituted or unsubstituted alkyl sulfone. In some embodiments, R5 is a substituted or unsubstituted alkyl. In some embodiments, R5 is H. In some embodiments, R5 is H, ethyl, butyl, CH2-CCH, CH2-C(O)-OCH3, or SO2-CH2-cyclopentyl, each being a separate embodiment of the present invention. In some embodiments, n is 0, 1, 2, or 3. In some embodiments, n is 1. In some embodiments, m is 1 or 2. In some embodiments, m is 1.

[0114] In some embodiments, substitutions include, but are not limited to, F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl (e.g., imidazole), C3-C8 cycloalkyl (e.g., cyclohexyl), CN, NO2, or any combination thereof.

[0115] In various embodiments, the compound is a herbicide compound. In various embodiments, the compound is intended for use in controlling the growth of undesirable plants.

[0116] In various embodiments, the present invention relates to a compound represented by the structure of formula I(h),

[0117] [ka]

[0118] During the ceremony, R1, R1', R2, and R2' are each independently H, F, Cl, Br, I, OH, SH, R8-OH (e.g., CH2-OH), R8-SH, and -R8-OR. 10 , (e.g., -CH2-O-CH3), R8-(C3-C8 cycloalkyl) (e.g., cyclohexyl), R8-(C3-C8 heterocyclic ring) (e.g., CH2-imidazole, CH2-indazole), CF3, CD3, OCD3, CN, NO2, -CH2CN, -R8CN, NH2, NHR, N(R)2, R8-N(R 10 )(R 11 )(For example, CH2-NH2, CH2-N(CH3)2), R9-R8-N(R 10 )(R 11 (For example, C≡C-CH2-NH2), B(OH)2, -OC(O)CF3, -OCH2Ph, NHC(O)-R 10 (For example, NHC(O)CH3), NHC(O)-N(R 10 )(R 11 (For example, NHC(O)N(CH3)2), COOH, -C(O)Ph, C(O)OR 10 (e.g. C(O)O-CH3, C(O)O-CH(CH3)2, C(O)O-CH2CH3), R8-C(O)-R 10 (For example, CH2C(O)CH3), C(O)H, C(O)-R 10 (e.g., C(O)-CH3, C(O)-CH2CH3, C(O)-CH2CH2CH3), C1-C5 linear or branched C(O)-haloalkyl (e.g., C(O)-CF3), -C(O)NH2, C(O)NHR, C(O)N(R) 10 )(R 11 )(For example, C(O)N(CH3)2), SO2R, SO2N(R 10 )(R 11)(e.g., SO2N(CH3)2, SO2NHC(O)CH3), C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, 2, 3, or 4-CH2-C6H4-Cl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl, benzyl), C1-C5 linear or branched, substituted or unsubstituted alkenyl (e.g., CH=C(Ph)2), C1-C5 linear or branched, or C3-C8 cyclic haloalkyl (e.g., CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2), C1-C5 linear or branched, or C3-C8 cyclic alkoxys (e.g., methoxy, ethoxy, propoxy, isopropoxy, O-CH2-cyclopropyl, O-cyclobutyl, O-cyclopentyl, O-cyclohexyl, 1-butoxy, 2-butoxy, O-tBu) (optionally, at least one methylene group (CH2) in the alkoxy is an oxygen atom (For example, substituted by O-1-oxacyclobutyl, O-2-oxacyclobutyl), C1-C5 linear or branched thioalkoxys, C1-C5 linear or branched haloalkoxys (for example, OCF3, OCHF2), C1-C5 linear or branched alkoxyalkyls, substituted or unsubstituted C3-C8 cycloalkyls (for example, cyclopropyl, cyclopentyl), substituted or unsubstituted C3-C8 heterocyclic rings (for example, 3-methyl-4H-1,2,4-triazole, 5-methyl-1,2,4) -Oxadiazole, thiophene, oxazole, oxadiazole, imidazole, furan, triazole, tetrazole, pyridine (2, 3, or 4-pyridine), 3-methyl-2-pyridine, pyrimidine, pyrazine, oxacyclobutane (1 or 2-oxacyclobutane, protonated or deprotonated pyridine oxide), substituted or unsubstituted aryl (e.g., phenyl), substituted or unsubstituted benzyl (e.g., benzyl, 4-Cl-benzyl, 4-OH-benzyl), Alternatively, R2 and R1 may be linked together to form a substituted or unsubstituted C3-C8 carboncyclic or heterocyclic ring. R3 can be H, F, Cl, Br, I, OH, SH, =O, R8-OH (e.g., CH2-OH), R8-SH, -R8-OR10 (For example, CH2-O-CH3)CF3, CD3, OCD3, CN, NO2, -CH2CN, -R8CN, NH2, NHNH2, NHR, N(R)2, R8-N(R 10 )(R 11 )(For example, CH2-NH2, CH2-N(CH3)2), R9-R8-N(R 10 )(R 11 ), B(OH)2, -OC(O)CF3, -OCH2Ph, NHC(O)OBz, -NHC(O)-R 10 (For example, NHC(O)CH3), NHC(O)-N(R 10 )(R 11 (For example, NHC(O)N(CH3)2), COOH, -C(O)Ph, C(O)OR 10 (For example, C(O)O-CH3, C(O)O-CH2CH3), R8-C(O)-R 10 (For example, CH2C(O)CH3), C(O)H, C(O)-R 10 (e.g., C(O)-CH3, C(O)-CH2CH3, C(O)-CH2CH2CH3), C1-C5 linear or branched C(O)-haloalkyl (e.g., C(O)-CF3), -C(O)NH2, C(O)NHR, C(O)N(R) 10 )(R 11 )(For example, C(O)N(CH3)2), SO2R, SO2N(R 10 )(R 11)(e.g., SO2N(CH3)2), C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, C(OH)(CH3)(Ph), ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl), C1-C5 linear or branched, or C3-C8 cyclic haloalkyl (e.g., CF3, CF2CH3, CF2-cyclobutyl, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2), C1-C5 linear or branched, or C3-C8 cyclic alkoxy (e.g., methoxy, ethoxy, propoxy, isopropoxy, O-CH2-cyclopropyl), C1-C5 linear or branched thiooxy, C1-C5 linear or branched haloalkoxy, C1-C5 linear or branched alkoxyalkyl, substituted or unsubstituted C3-C8 cycloalkyl (e.g., cyclopropyl, cyclopentyl), substituted or unsubstituted C3-C8 heterocyclic ring (e.g., 3-methyl-4H-1,2,4-triazole, 5-methyl-1,2,4-oxadiazole, thiophene, oxazole, isoxazole, imidazole, furan, triazole, pyridine (2,3, or 4-pyridine), pyrimidine, pyrazine, oxacyclobutane (1 or 2-oxacyclobutane), indole), substituted or unsubstituted aryl (e.g., phenyl), R4 is NHNH2, R5 is H, C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, CH2SH, ethyl, butyl, CH2-CCH, isopropyl, CH2-C(O)-OCH3), C2-C5 linear or branched, substituted or unsubstituted alkenyl, C2-C5 linear or branched, substituted or unsubstituted alkynyl (e.g., CCH, CH2-CCH), C1-C5 linear or branched haloalkyl (e.g., CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2), R8-aryl (e.g., CH2-Ph), C(=CH2)-R 10(For example, C(=CH2)-C(O)-OCH3, C(=CH2)-CN), substituted or unsubstituted alkyl sulfones (for example, SO2-CH2-cyclopentyl), substituted or unsubstituted aryl compounds (for example, phenyl), substituted or unsubstituted heteroaryl compounds (for example, pyridine (2,3, and 4-pyridine)), R8 is [CH2] p And, p is between 1 and 10. R9, [CH] q [C] q And, q is between 2 and 10, R 10 and R 11 However, each is independently H, CN, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH3)), or S(O)2R, Or R 10 and R 11 However, they link together to form substituted or unsubstituted C3-C8 heterocyclic rings (e.g., piperazine, piperidine), R is H, a C1-C5 linear or branched alkyl (e.g., methyl, ethyl), a C1-C5 linear or branched alkoxy (e.g., methoxy), a phenyl, an aryl, or a heteroaryl, or two gem R substituents are linked together to form a 5 or 6-membered heterocyclic ring. m is an integer between 1 and 5 (for example, 1 or 2), n is an integer between 0 and 5 (for example, 0, 1, 2, or 3), X1 is S, O, N-OH, CH2, C(R)2, or N-OMe. Is X2 S, O, N-OH, CH2, C(R)2, or N-OMe? Alternatively, X2 may link with the adjacent carbon of X1 to form ring B represented by the following structure (in which case X1 is X7),

[0119] [ka]

[0120] If X4, X5, X6, and X7 are each independently C or N, and any of X4, X5, X6, and X7 is N, then each substitution R 90 , R 60 , R 70 , or R 80 However, it does not exist. R 60 , R 70 , R 80 , and R 90 However, each is independent of H, F, Cl, Br, I, OH, SH, R8-OH, R8-SH, -R8-OR 10 , CF3, CN, NO2, NH2, NHR, N(R)2, R8-N(R 10 )(R 11 ), -OC(O)CF3, -OCH2Ph, NHC(O)OBz, -NHC(O)-R 10 COOH, -C(O)Ph, C(O)OR 10 C(O)H, C(O)-R 10 , C1-C5 linear or branched C(O)-haloalkyl, -C(O)NH2, C(O)NHR, C(O)N(R 10 )(R 11 ), SO2R, SO2N(R 10 )(R 11 ), selected from C1-C5 linear or branched saturated or unsaturated alkyl, C1-C5 linear or branched, or C3-C8 cyclic haloalkyl, C1-C5 linear or branched, or C3-C8 cyclic alkoxy, C1-C5 linear or branched thioalkoxy, C1-C5 linear or branched haloalkoxy, C1-C5 linear or branched alkoxyalkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C3-C8 heterocyclic ring, substituted or unsubstituted aryl, X3 is O, NH, or NR 50 And, R 50 However, this relates to compounds that are H, or C1-C5 linear or branched, substituted or unsubstituted alkyl groups, or their pesticide-acceptable salts, stereoisomers, tautomers, hydrates, N-oxides, reverse amide analogs, isotopic variants (e.g., deuterated analogs), or any combination thereof.

[0121] In some embodiments, substitutions include, but are not limited to, F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl (e.g., imidazole), C3-C8 cycloalkyl (e.g., cyclohexyl), CN, NO2, or any combination thereof.

[0122] In various embodiments, the compound is a herbicide compound. In various embodiments, the compound is intended for use in controlling the growth of undesirable plants.

[0123] In various embodiments, the present invention relates to a compound represented by the structure of formula (X),

[0124] [ka]

[0125] During the ceremony, A is either C3-C7 cycloalkyl or absent (e.g., cyclohexyl, cyclopropyl, cyclobutyl), B is a 5-7 member nitrogen-containing heterocyclic ring, or is absent (e.g., pyrrolidine, piperidine), C is a C5-C7 substituted or unsubstituted cycloalkyl, an aromatic ring, or is absent (e.g., phenyl, cyclopentyl, cyclohexyl), D is either a C5-C7 cycloalkyl group or absent (e.g., cyclopentyl). E is a substituted or unsubstituted 5-7 member nitrogen-containing heterocyclic ring, or is absent (e.g., pyrrolidine, piperidine, oxazolidine-2-one), If at least one of rings A, B, C, D, or E does not exist, R5 is H, C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, CH2SH, ethyl, butyl, CH2-CCH, isopropyl, CH2-C(O)-OCH3), C2-C5 linear or branched, substituted or unsubstituted alkenyl, C2-C5 linear or branched, substituted or unsubstituted alkynyl (e.g., CCH, CH2-CCH), C1-C5 linear or branched haloalkyl (e.g., CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2), R8-aryl (e.g., CH2-Ph), C(=CH2)-R 10 (For example, C(=CH2)-C(O)-OCH3, C(=CH2)-CN), substituted or unsubstituted aryls (for example, phenyl), substituted or unsubstituted heteroaryls (for example, pyridine (2,3, and 4-pyridine)), R8 is [CH2] p And, p is between 1 and 10. R9, [CH] q [C] q And, q is between 2 and 10, R 10 and R 11 However, each is independently either H, CN, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH3)), or S(O)2R, or R 10 and R 11 However, they link together to form substituted or unsubstituted C3-C8 heterocyclic rings (e.g., piperazine, piperidine), R is H, a C1-C5 linear or branched alkyl (e.g., methyl, ethyl), a C1-C5 linear or branched alkoxy (e.g., methoxy), a phenyl, an aryl, or a heteroaryl, or two gem R substituents are linked together to form a 5 or 6-membered heterocyclic ring. n is an integer between 0 and 2. X1 is S, O, CH2, CH(R), or C(R)2. X2 is S, O, CH2, CH(R), or C(R)2. This relates to compounds, or their pesticide-permissible salts, stereoisomers, tautomers, hydrates, N-oxides, reverse amide analogs, isotopic variants (e.g., deuterated analogs), or any combination thereof.

[0126] In some embodiments, at least one of rings A to E of the compound of formula (X) is not absent. In some embodiments, only one of rings A to E is not absent. In some embodiments, A is absent. In some embodiments, A is cyclohexyl. In some embodiments, A is cyclopropyl. In some embodiments, A is cyclobutyl. In some embodiments, B is absent. In some embodiments, B is pyrrolidine. In some embodiments, B is piperidine. In some embodiments, C is absent. In some embodiments, C is a C5-C7 substituted or unsubstituted cycloalkyl. In some embodiments, C is cyclopentyl. In some embodiments, C is cyclohexyl. In some embodiments, C is an aromatic ring. In some embodiments, C is phenyl. In some embodiments, D is absent. In some embodiments, D is cyclopentyl. In some embodiments, E is absent. In some embodiments, E is pyrrolidine. In some embodiments, E is piperidine. In some embodiments, E is oxazolidine-2-one. In some embodiments, E is a substituted oxazolidine-2-one. In some embodiments, X1 is S. In some embodiments, X1 is O. In some embodiments, X1 is CH2. In some embodiments, X2 is S. In some embodiments, X2 is O. In some embodiments, X2 is CH2. In some embodiments, n is 0. In some embodiments, n is 1. In some embodiments, n is 2. In some embodiments, R5 is H. In some embodiments, R5 is a C1-C5 linear or branched substituted or unsubstituted alkyl group. In some embodiments, R5 is ethyl. In some embodiments, R5 is butyl. In some embodiments, R5 is CH2-C≡CH.

[0127] In some embodiments, substitutions include, but are not limited to, F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl (e.g., imidazole), C3-C8 cycloalkyl (e.g., cyclohexyl), CN, NO2, or any combination thereof.

[0128] In various embodiments, the compound is a herbicide compound. In various embodiments, the compound is intended for use in controlling undesirable plant growth. In various embodiments, the compound is compound 105, 106, 123, 124, 125, 126, 129, 130, 131, 132, 133, 134, 138, 139, 143, 145, 146, 147, 148, 150, 152, 153, 154, 155, 165, 166, 167, 168, or 171, each representing a distinct embodiment according to the present invention.

[0129] In various embodiments, the present invention relates to a compound represented by the structure of formula X(a),

[0130] [ka]

[0131] During the ceremony, R5 is H, C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, CH2SH, ethyl, butyl, CH2-CCH, isopropyl, CH2-C(O)-OCH3), C2-C5 linear or branched, substituted or unsubstituted alkenyl, C2-C5 linear or branched, substituted or unsubstituted alkynyl (e.g., CCH, CH2-CCH), C1-C5 linear or branched haloalkyl (e.g., CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2), R8-aryl (e.g., CH2-Ph), C(=CH2)-R 10 (For example, C(=CH2)-C(O)-OCH3, C(=CH2)-CN), substituted or unsubstituted aryls (for example, phenyl), substituted or unsubstituted heteroaryls (for example, pyridine (2,3, and 4-pyridine)), R8 is [CH2] p And, p is between 1 and 10. R9, [CH] q [C] q And, q is between 2 and 10, R 10 and R 11 However, each is independently H, CN, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH3)), or S(O)2R, Or R 10 and R 11 However, they link together to form substituted or unsubstituted C3-C8 heterocyclic rings (e.g., piperazine, piperidine), R is H, a C1-C5 linear or branched alkyl (e.g., methyl, ethyl), a C1-C5 linear or branched alkoxy (e.g., methoxy), a phenyl, an aryl, or a heteroaryl, or two gem R substituents are linked together to form a 5 or 6-membered heterocyclic ring. X1 is S, O, CH2, CH(R), or C(R)2. n and o are each independent integers between 0 and 2. m is an integer between 1 and 3. This relates to compounds, or their pesticide-permissible salts, stereoisomers, tautomers, hydrates, N-oxides, reverse amide analogs, isotopic variants (e.g., deuterated analogs), or any combination thereof.

[0132] In some embodiments, m of the compound of formula X(a) is 1. In some embodiments, m is 2. In some embodiments, m is 1 or 2. In some embodiments, o is 0. In some embodiments, o is 1. In some embodiments, o is 0 or 1. In some embodiments, n is 0. In some embodiments, n is 1. In some embodiments, n is 2. In some embodiments, n is 0 or 1. In some embodiments, n is 1 or 2. In some embodiments, X1 is CH2. In some embodiments, X1 is S. In some embodiments, X1 is O. In some embodiments, R5 is H. In some embodiments, R5 is a C1-C5 linear or branched substituted or unsubstituted alkyl. In some embodiments, R5 is ethyl. In some embodiments, R5 is butyl. In some embodiments, R5 is a substituted alkyl. In some embodiments, R5 is CH2-C≡CH. In some embodiments, R5 is not H. In some embodiments, X1 is CH2, m is 2, n is 1, and R5 is a substituted or unsubstituted alkyl group. In some embodiments, X1 is CH2, m is 2, n is 1, o is 1, and R5 is a substituted or unsubstituted alkyl group. In some embodiments, X1 is O or S, m is 1 or 2, n is 1 or 2, o is 0 or 1, and R5 is H. In some embodiments, if R5 is H, X1 is not CH2. In some embodiments, if X1 is O and R5 is H, n is not 1. In some embodiments, if X1 is O, n is not 1.

[0133] In some embodiments, substitutions include, but are not limited to, F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl (e.g., imidazole), C3-C8 cycloalkyl (e.g., cyclohexyl), CN, NO2, or any combination thereof.

[0134] In various embodiments, the compound of formula X(a) is represented by one of the following structures.

[0135] [Table 1]

[0136] In various embodiments, the compound is a herbicide compound. In various embodiments, the compound is intended for use in controlling the growth of undesirable plants.

[0137] In various embodiments, the present invention relates to a compound represented by the structure of formula X(b),

[0138] [ka]

[0139] During the ceremony, R5 is H, C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, CH2SH, ethyl, butyl, CH2-CCH, isopropyl, CH2-C(O)-OCH3), C2-C5 linear or branched, substituted or unsubstituted alkenyl, C2-C5 linear or branched, substituted or unsubstituted alkynyl (e.g., CCH, CH2-CCH), C1-C5 linear or branched haloalkyl (e.g., CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2), R8-aryl (e.g., CH2-Ph), C(=CH2)-R 10 (For example, C(=CH2)-C(O)-OCH3, C(=CH2)-CN), substituted or unsubstituted aryls (for example, phenyl), substituted or unsubstituted heteroaryls (for example, pyridine (2,3, and 4-pyridine)), R8 is [CH2] p And, p is between 1 and 10. R9, [CH] q [C] q And, q is between 2 and 10, R 10 and R 11 However, each is independently H, CN, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH3)), or S(O)2R, Or R 10 and R 11 However, they link together to form substituted or unsubstituted C3-C8 heterocyclic rings (e.g., piperazine, piperidine), R is H, a C1-C5 linear or branched alkyl (e.g., methyl, ethyl), a C1-C5 linear or branched alkoxy (e.g., methoxy), a phenyl, an aryl, or a heteroaryl, or two gem R substituents are linked together to form a 5 or 6-membered heterocyclic ring. X1 is S, O, CH2, CH(R), or C(R)2. X2 is S, O, CH2, CH(R), or C(R)2. n is an integer between 0 and 2. m is an integer between 1 and 3. This relates to compounds, or their pesticide-permissible salts, stereoisomers, tautomers, hydrates, N-oxides, reverse amide analogs, isotopic variants (e.g., deuterated analogs), or any combination thereof.

[0140] In some embodiments, m of the compound of formula X(b) is 1. In some embodiments, m is 2. In some embodiments, m is 1 or 2. In some embodiments, n is 0. In some embodiments, n is 1. In some embodiments, n is 0 or 1. In some embodiments, X1 is CH2. In some embodiments, X2 is CH2. In some embodiments, X1 and X2 are CH2. In some embodiments, R5 is H.

[0141] In some embodiments, substitutions include, but are not limited to, F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl (e.g., imidazole), C3-C8 cycloalkyl (e.g., cyclohexyl), CN, NO2, or any combination thereof.

[0142] In various embodiments, the compound of formula X(b) is represented by one of the following structures.

[0143] [Table 2]

[0144] In various embodiments, the compound is a herbicide compound. In various embodiments, the compound is intended for use in controlling the growth of undesirable plants.

[0145] In various embodiments, the present invention relates to a compound represented by the structure of formula X(c),

[0146] [ka]

[0147] During the ceremony, R5 is H, C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, CH2SH, ethyl, butyl, CH2-CCH, isopropyl, CH2-C(O)-OCH3), C2-C5 linear or branched, substituted or unsubstituted alkenyl, C2-C5 linear or branched, substituted or unsubstituted alkynyl (e.g., CCH, CH2-CCH), C1-C5 linear or branched haloalkyl (e.g., CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2), R8-aryl (e.g., CH2-Ph), C(=CH2)-R 10 (For example, C(=CH2)-C(O)-OCH3, C(=CH2)-CN), substituted or unsubstituted aryls (for example, phenyl), substituted or unsubstituted heteroaryls (for example, pyridine (2,3, and 4-pyridine)), R8 is [CH2] p And, p is between 1 and 10. R9, [CH] q [C] q And, q is between 2 and 10, R 10 and R 11 However, each is independently H, CN, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH3)), or S(O)2R, Or R 10 and R11 However, they link together to form substituted or unsubstituted C3-C8 heterocyclic rings (e.g., piperazine, piperidine), R is H, a C1-C5 linear or branched alkyl (e.g., methyl, ethyl), a C1-C5 linear or branched alkoxy (e.g., methoxy), a phenyl, an aryl, or a heteroaryl, or two gem R substituents are linked together to form a 5 or 6-membered heterocyclic ring. X1 is S, O, CH2, CH(R), or C(R)2. X2 is S, O, CH2, CH(R), or C(R)2. n is an integer between 0 and 2. m is an integer between 1 and 3. This relates to compounds, or their pesticide-permissible salts, stereoisomers, tautomers, hydrates, N-oxides, reverse amide analogs, isotopic variants (e.g., deuterated analogs), or any combination thereof.

[0148] In some embodiments, m of the compound of formula X(c) is 1. In some embodiments, m is 2. In some embodiments, m is 1 or 2. In some embodiments, n is 0. In some embodiments, n is 1. In some embodiments, n is 0 or 1. In some embodiments, X1 is CH2. In some embodiments, X2 is CH2. In some embodiments, X2 is S. In some embodiments, X2 is O. In some embodiments, X1 and X2 are CH2. In some embodiments, R5 is H. In some embodiments, R5 is a substituted or unsubstituted alkyl. In some embodiments, R5 is methyl. In some embodiments, X1 and X2 are CH2, n is 1, and m is 1 or 2. In some embodiments, n is 1, R5 is H, and m is 1 or 2.

[0149] In some embodiments, substitutions include, but are not limited to, F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl (e.g., imidazole), C3-C8 cycloalkyl (e.g., cyclohexyl), CN, NO2, or any combination thereof.

[0150] In various embodiments, the compound of formula X(c) is represented by one of the following structures.

[0151] [Table 3]

[0152] In various embodiments, the compound is a herbicide compound. In various embodiments, the compound is intended for use in controlling the growth of undesirable plants.

[0153] In various embodiments, the present invention relates to a compound represented by the structure of formula X(d),

[0154] [ka]

[0155] During the ceremony, R5 is H, C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, CH2SH, ethyl, butyl, CH2-CCH, isopropyl, CH2-C(O)-OCH3), C2-C5 linear or branched, substituted or unsubstituted alkenyl, C2-C5 linear or branched, substituted or unsubstituted alkynyl (e.g., CCH, CH2-CCH), C1-C5 linear or branched haloalkyl (e.g., CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2), R8-aryl (e.g., CH2-Ph), C(=CH2)-R 10 (For example, C(=CH2)-C(O)-OCH3, C(=CH2)-CN), substituted or unsubstituted aryls (for example, phenyl), substituted or unsubstituted heteroaryls (for example, pyridine (2,3, and 4-pyridine)), R8 is [CH2] p And, p is between 1 and 10. R9, [CH] q [C] q And, q is between 2 and 10, R 10 and R 11 However, each is independently H, CN, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH3)), or S(O)2R, Or R 10 and R 11 However, they link together to form substituted or unsubstituted C3-C8 heterocyclic rings (e.g., piperazine, piperidine), R is H, a C1-C5 linear or branched alkyl (e.g., methyl, ethyl), a C1-C5 linear or branched alkoxy (e.g., methoxy), a phenyl, an aryl, or a heteroaryl, or two gem R substituents are linked together to form a 5 or 6-membered heterocyclic ring. X2 is S, O, CH2, CH(R), or C(R)2. n is an integer between 0 and 2. m is an integer between 1 and 3. This relates to compounds, or their pesticide-permissible salts, stereoisomers, tautomers, hydrates, N-oxides, reverse amide analogs, isotopic variants (e.g., deuterated analogs), or any combination thereof.

[0156] In some embodiments, m of the compound of formula X(d) is 1. In some embodiments, m is 2. In some embodiments, m is 1 or 2. In some embodiments, n is 1. In some embodiments, n is 2. In some embodiments, n is 1 or 2. In some embodiments, X2 is CH2. In some embodiments, R5 is H. In some embodiments, R5 is H, n is 2, and m is 1. In some embodiments, R5 is H, X2 is CH2, n is 2, and m is 1.

[0157] In some embodiments, substitutions include, but are not limited to, F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl (e.g., imidazole), C3-C8 cycloalkyl (e.g., cyclohexyl), CN, NO2, or any combination thereof.

[0158] In various embodiments, the compound of formula X(d) is represented by one of the following structures.

[0159] [Table 4]

[0160] In various embodiments, the compound is a herbicide compound. In various embodiments, the compound is intended for use in controlling the growth of undesirable plants.

[0161] In various embodiments, the present invention relates to a compound represented by any one of the following structures.

[0162] [Table 5-1] [Table 5-2] [Table 5-3]

[0163] In various embodiments, the compound is a herbicide compound. In various embodiments, the compound is intended for use in controlling the growth of undesirable plants.

[0164] In various embodiments, the present invention relates to the use of herbicidal compounds and / or compounds represented by any one of the following structures, or pesticide compositions thereof, for controlling the growth of undesirable plants.

[0165] [Table 6-1] [Table 6-2] [Table 6-3] [Table 6-4] [Table 6-5] [Table 6-6]

[0166] In various embodiments, ring A of compounds of formulas I, I(a), I(b), I(g), and I(ga) has one chiral center (i.e., R2 and R2' are the same). In various embodiments, C of ring A of formula I(a) or I(b) B It is achiral (i.e., R2 and R2' are the same). In various embodiments, C of ring A B It is chiral. In various embodiments, ring A has two chiral centers (i.e., R2 and R2' are distinct). In various embodiments, the compound is a single stereoisomer. In various embodiments, the compound is a single enantiomer.

[0167] In various embodiments, the compound comprises a substantially pure stereoisomer. By substantially pure, the stereoisomer is intended to be at least about 90% pure, more preferably at least about 95% pure, even more preferably at least about 98% pure, and most preferably at least about 99% pure. In various embodiments, the compound comprises a single stereoisomer with purity levels of >80%, >85%, >90%, >91%, >92%, >93%, >94%, >95%, >96%, >97%, >98%, >99%, and >99.5% enantiomer excess (ee), each representing a distinct embodiment according to the present invention. In various embodiments, the compound contains a single stereoisomer with enantiomer ratios (er) of purity >80%, >85%, >90%, >91%, >92%, >93%, >94%, >95%, >96%, >97%, >98%, >99%, and >99.5%, each representing a distinct embodiment of the present invention. In various embodiments, the compound contains a single stereoisomer with purity higher than 80%, 85%, 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99%, and 99.5%, each representing a distinct embodiment of the present invention.

[0168] In various embodiments, the compound is a substantially pure single enantiomer. In various embodiments, the compound contains a mixture of stereoisomers. In various embodiments, the compound contains a mixture of enantiomers. In various embodiments, the compound is a racemate.

[0169] In various embodiments, the compound has two chiral centers. In various embodiments, the compound comprises a mixture of stereoisomers. In various embodiments, the compound comprises a mixture of two, three, or four stereoisomers, each representing a distinct embodiment according to the present invention. In various embodiments, the compound is a single stereoisomer. In various embodiments, the compound is a substantially pure single stereoisomer. In various embodiments, the substantially pure stereoisomer is compound 104, 105, 106, 114, 115, 116, 117, 118, or 119 described below herein, each representing a distinct embodiment according to the present invention. In various embodiments, the substantially pure stereoisomer has a purity of at least 80%, 85%, 90%, 95%, 97%, 98%, or 99%, each representing a distinct embodiment according to the present invention. In various embodiments, the compound is a substantially pure RR stereoisomer. In various embodiments, the compound is a substantially pure SS stereoisomer. In various embodiments, the compound is a substantially pure RS stereoisomer. In various embodiments, the compound is 5-((4R,5S)-5-methyl-2-oxoxazolidine-4-yl)pentanoic acid. In various embodiments, the compound is compound 106. In various embodiments, the compound is a substantially pure SR stereoisomer. In various embodiments, the compound is (6S,7R)-6-amino-7-hydroxyoctanoic acid. In various embodiments, the compound is compound 104. In various embodiments, the compound is 5-((4S,5R)-5-methyl-2-oxoxazolidine-4-yl)pentanoic acid. In various embodiments, the compound is compound 105. In various embodiments, the compound is not (6R,7S)-6-amino-7-hydroxyoctanoic acid. In various embodiments, the compound is not 5-((4R,5S)-5-methyl-2-oxoxazolidine-4-yl)pentanoic acid.

[0170] In some embodiments, A in formulas I, I(a), I(b), I(g), or I(ga) does not exist. In some embodiments, A in formula I is a substituted or unsubstituted single or condensed aromatic ring system or a heteroaromatic ring system, or a substituted or unsubstituted single or condensed C3-C 10 Cycloalkyl, or single or condensed C3-C 10 It is a heterocyclic ring. In some embodiments, A in formula I is a substituted or unsubstituted single or fused aromatic ring system or a heteroaromatic ring system, or a substituted or unsubstituted single or fused C4-C 10 Cycloalkyl, or single or condensed C4-C 10 It is a heterocyclic ring. In some embodiments, A is a monoaromatic ring system. In some embodiments, A is a substituted aryl. In some embodiments, the aryl is substituted with NH2. In some embodiments, A is a monoaromatic ring. In some embodiments, A is a monoC3-C 10 It is a cycloalkyl group. In some embodiments, A is a substituted single C3-C 10 It is a cycloalkyl group. In some embodiments, A is a single C4-C 10 It is a cycloalkyl group. In some embodiments, A is a substituted single C4-C 10It is a cycloalkyl compound. In some embodiments, A is cyclopropyl. In some embodiments, A is cyclobutyl. In some embodiments, A is cyclopentyl. In some embodiments, A is cyclohexyl. In some embodiments, A is further substituted with at least one selected from F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl (e.g., imidazole), C3-C8 cycloalkyl (e.g., cyclohexyl), CN, and NO2, each representing a distinct embodiment according to the present invention. 。 In some embodiments, A is further substituted with NH2. In some embodiments, A is a cycloalkyl group substituted with NH2. In some embodiments, the cycloalkyl group is cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl, each representing a distinct embodiment according to the present invention. In some embodiments, A is a single C3-C 10 It is a complex ring. In some embodiments, A is a single C4-C 10It is a heterocyclic ring. In some embodiments, A is a substituted oxazolidine-2-one ring. In some embodiments, A is an alkyl-substituted oxazolidine-2-one ring. In some embodiments, A is 5-methyloxazolidine-2-one. In some embodiments, A is a nitrogen-containing heterocyclic ring. In some embodiments, A is 1, 2, or 3-pyrrolidine, each representing a distinct embodiment according to the present invention. In some embodiments, A is tetrahydropyridine. In some embodiments, A is 5,6-dihydro-4H-1,3-thiazine. In some embodiments, A is 4,5-dihydro-1H-imidazole. In some embodiments, A is 2, 3, or 4-pyridine, each representing a distinct embodiment according to the present invention. In some embodiments, pyridine is further substituted with at least NH2. In some embodiments, A is tetrahydropyrimidine. In some embodiments, A is 1, 2, or 3-piperidine, each representing a distinct embodiment according to the present invention. In some embodiments, A is an imidazole. In some embodiments, the nitrogen-containing heterocyclic ring is further substituted with at least NH2. In some embodiments, A is a condensed aromatic ring system. In some embodiments, A is a condensed heteroaromatic ring system. In some embodiments, A is a condensed C3-C 10 It is a cycloalkyl group. In some embodiments, A is a condensed C3-C 10It is a heterocyclic ring system. In some embodiments, A is phenyl. In other embodiments, A is pyridinyl. In other embodiments, A is 2-pyridinyl. In other embodiments, A is 3-pyridinyl. In other embodiments, A is 4-pyridinyl. In other embodiments, A is naphthyl. In other embodiments, A is benzothiazolyl. In other embodiments, A is benzimidazolyl. In other embodiments, A is quinolinyl. In other embodiments, A is isoquinolinyl. In other embodiments, A is indolyl. In other embodiments, A is tetrahydronaphthyl. In other embodiments, A is indenyl. In other embodiments, A is benzofuran-2(3H)-one. In other embodiments, A is benzo[d][1,3]dioxole. In other embodiments, A is naphthalene. In other embodiments, A is tetrahydrothiophene 1,1-dioxide. In other embodiments, A is thiazole. In other embodiments, A is benzimidazole. In other embodiments, A is piperidine. In other embodiments, A is 1-methylpiperidine. In other embodiments, A is imidazole. In other embodiments, A is 1-methylimidazole. In other embodiments, A is thiophene. In other embodiments, A is isoquinoline. In other embodiments, A is indole. In other embodiments, A is 1,3-dihydroisobenzofuran. In other embodiments, A is benzofuran. In other embodiments, A is single or condensed C3-C 10It is a cycloalkyl ring. In other embodiments, A is cyclohexyl. In some embodiments, A may be further substituted with at least one substituent selected from F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl (e.g., imidazole), C3-C8 cycloalkyl (e.g., cyclohexyl), CN, and NO2, each representing a distinct embodiment according to the present invention. In some embodiments, A may be further substituted with NH2.

[0171] In some embodiments, ring A of formulas I, I(a), I(b), I(g), and / or I(ga) is represented by the following structure:

[0172] [ka]

[0173] In the formula, R2 and R2' are defined as follows:

[0174] The wavy line in ring A above represents the rest of the molecule (i.e., -(C(R1)(R1')) of formulas I, I(a), I(b), I(g), or I(ga)). n It is understood that this represents the connection point between A and ).

[0175] In some embodiments, ring B of formulas I, I(a), I(b), I(f), and / or I(h) is absent. In other embodiments, ring B is pyridine.

[0176] In some embodiments, ring B of formula I is a single or condensed aromatic ring system or a heteroaromatic ring system, or a single or condensed C3-C 10 Cycloalkyl, or single or condensed C3-C10 It is a heterocyclic ring. In some embodiments, ring B is a monoaromatic ring system (i.e., allene). In some embodiments, ring B is a monoaromatic ring (e.g., pyridine). In some embodiments, ring B is a monoC3-C 10 It is a cycloalkyl group. In some embodiments, ring B is a single C3-C 10 It is a heterocyclic ring. In some embodiments, ring B is a fused aromatic ring system. In some embodiments, ring B is a fused heteroaromatic ring system. In some embodiments, ring B is a fused C3-C 10 It is a cycloalkyl ring. In some embodiments, ring B is a condensed C3-C 10 It is a heterocyclic ring system. In some embodiments, ring B is an allene. In other embodiments, ring B is a pyridine ring. In other embodiments, ring B is a pyrazine. In other embodiments, ring B is a pyridazine. In other embodiments, ring B is a pyrimidine. In other embodiments, ring B is a triazine. In other embodiments, ring B is a tetrazine. In some embodiments, ring B is F, Cl, Br, I, OH, SH, R8-OH, R8-SH, -R8-OR 10 , CF3, CN, NO2, NH2, NHR, N(R)2, R8-N(R 10 )(R 11 ), -OC(O)CF3, -OCH2Ph, NHC(O)OBz, -NHC(O)-R 10 COOH, -C(O)Ph, C(O)OR 10 C(O)H, C(O)-R 10 , C1-C5 linear or branched C(O)-haloalkyl, -C(O)NH2, C(O)NHR, C(O)N(R 10 )(R 11 ), SO2R, SO2N(R 10 )(R 11), C1-C5 linear or branched, or C3-C8 cyclic haloalkyl, C1-C5 linear or branched, or C3-C8 cyclic alkoxy, C1-C5 linear or branched thioalkoxy, C1-C5 linear or branched haloalkoxy, C1-C5 linear or branched alkoxyalkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C3-C8 heterocyclic ring, substituted or unsubstituted aryl, (O)-CH3, C1-C5 linear or branched, substituted or unsubstituted alkyl, methyl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl, benzyl, or any combination thereof, each representing a separate embodiment according to the present invention.

[0177] In some embodiments, ring B of formulas I, I(a), I(b), I(f), and / or I(h) is represented by the following structure.

[0178] [ka]

[0179] In such cases, X1 in equations I, I(a), I(b), I(f), and I(h) is represented by X7 in ring B, where X4, X5, X6, and X7, R 90 , R 60 , R 70 , and R 80 It is defined as follows:

[0180] The wavy line in ring B above represents the rest of the molecule (i.e., -(C(R1)(R1')) from the left). n It is understood that this represents the connection point of ring B with the carbonyl carbon atom from the right.

[0181] In some embodiments, R1 of compounds of formula I and / or I(a) to I(h) is independently H. In some embodiments, R1 is independently F, Cl, Br, or I, each representing a separate embodiment according to the present invention. In some embodiments, R1 is C(O)-R 10 And R 10 R1 is defined as follows: In some embodiments, R1 is C(O)-CH3. In some embodiments, R1 is independently a C1-C5 linear or branched substituted or unsubstituted alkyl group. In some embodiments, R1 is methyl. In some embodiments, R1 is ethyl. In some embodiments, R1 is isopropyl. In some embodiments, R1 is independently methyl, 2, 3, or 4-CH2-C6H4-Cl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl, or benzyl, each representing a distinct embodiment according to the present invention. In some embodiments, R1 is independently OH, SH, R8-OH, CH2-OH, R8-SH, or -R8-OR 10 -CH2-O-CH3, R8-(C3-C8 cycloalkyl), CH2-cyclohexyl, R8-(C3-C8 heterocyclic ring), CH2-imidazole, CH2-indazole, CD3, OCD3, CN, NO2, -CH2CN, -R8CN, NH2, NHR, N(R)2, R8-N(R 10 )(R 11 ), CH2-NH2, CH2-N(CH3)2, R9-R8-N(R 10 )(R 11 ), C≡C-CH2-NH2, B(OH)2, -OC(O)CF3, -OCH2Ph, NHC(O)-R 10 , NHC(O)CH3, NHC(O)-N(R 10 )(R 11 ), NHC(O)N(CH3)2, COOH, -C(O)Ph, C(O)OR 10 , C(O)O-CH3, C(O)O-CH(CH3)2, C(O)O-CH2CH3, R8-C(O)-R 10 , CH2C(O)CH3, C(O)H, C(O)-R10 C(O)-CH3, C(O)-CH2CH3, C(O)-CH2CH2CH3, C1-C5 linear or branched C(O)-haloalkyl, C(O)-CF3, -C(O)NH2, C(O)NHR, C(O)N(R) 10 )(R 11 ), C(O)N(CH3)2, SO2R, SO2N(R 10 )(R 11), SO2N(CH3)2, SO2NHC(O)CH3, C1-C5 linear or branched saturated or unsaturated alkyl, methyl, 2, 3, or 4-CH2-C6H4-Cl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl, benzyl, C1-C5 linear or branched saturated or unsaturated alkenyl, CH=C(Ph)2, C1-C5 linear or branched, or C3-C8 cyclic haloalkyl, CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2, C1-C5 linear or branched, or C3-C8 cyclic alkoxy, methoxy, ethoxy, propoxy, isopropoxy, O-CH2-cyclopropyl, O-cyclobutyl, O-cyclopentyl, O-cyclohexyl, 1-butoxy, 2-butoxy, O-tBu, C1-C5 linear or branched, or C3-C8 cyclic alkoxy (at least one methylene group (CH2) in the alkoxy is an oxygen source (substituted by), O-1-oxacyclobutyl, O-2-oxacyclobutyl, C1-C5 linear or branched thioalkoxy, C1-C5 linear or branched haloalkoxy, OCF3, OCHF2, C1-C5 linear or branched alkoxyalkyl, substituted or unsubstituted C3-C8 cycloalkyl (e.g., cyclopropyl, cyclopentyl), substituted or unsubstituted C3-C8 heterocyclic ring, 3-methyl-4H-1,2,4-triazole, 5-methyl-1,2,4-oxadiazole, Thiophene, oxazole, oxadiazole, imidazole, furan, triazole, tetrazole, pyridine (2, 3, or 4-pyridine), 3-methyl-2-pyridine, pyromidine, pyrazine, oxacyclobutane (1 or 2-oxacyclobutane), indole, protonated or deprotonated pyridine oxide, substituted or unsubstituted aryl, phenyl, substituted or unsubstituted benzyl, 4-Cl-benzyl, 4-OH-benzyl, each representing a distinct embodiment of the present invention. In some embodiments, R1 is H, C1-C5 linear or branched, unsubstituted alkyl, methyl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl, benzyl, C(O)-R 10, or C(O)-CH3, each representing a distinct embodiment according to the present invention. In some embodiments, each R1 is further substituted with at least one substitution selected from F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl (e.g., imidazole), C3-C8 cycloalkyl (e.g., cyclohexyl), CN, and NO2, each representing a distinct embodiment according to the present invention.

[0182] In some embodiments, R1' of compounds of formula I and / or I(a) to I(h) is independently H. In some embodiments, R1' is independently F, Cl, Br, or I, each representing a separate embodiment according to the present invention. In some embodiments, R1' is C(O)-R 10 And R 10 R1' is defined as follows: In some embodiments, R1' is C(O)-CH3. In some embodiments, R1' is independently a C1-C5 linear or branched substituted or unsubstituted alkyl group. In some embodiments, R1' is methyl. In some embodiments, R1' is ethyl. In some embodiments, R1' is isopropyl. In some embodiments, R1' is methyl, 2, 3, or 4-CH2-C6H4-Cl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl, or benzyl, each representing a distinct embodiment according to the present invention. In some embodiments, R1' is independently OH, SH, R8-OH, CH2-OH, R8-SH, or -R8-OR 10-CH2-O-CH3, R8-(C3-C8 cycloalkyl), CH2-cyclohexyl, R8-(C3-C8 heterocyclic ring), CH2-imidazole, CH2-indazole, CD3, OCD3, CN, NO2, -CH2CN, -R8CN, NH2, NHR, N(R)2, R8-N(R 10 )(R 11 ), CH2-NH2, CH2-N(CH3)2, R9-R8-N(R 10 )(R 11 ), C≡C-CH2-NH2, B(OH)2, -OC(O)CF3, -OCH2Ph, NHC(O)-R 10 , NHC(O)CH3, NHC(O)-N(R 10 )(R 11 ), NHC(O)N(CH3)2, COOH, -C(O)Ph, C(O)OR 10 , C(O)O-CH3, C(O)O-CH(CH3)2, C(O)O-CH2CH3, R8-C(O)-R 10 , CH2C(O)CH3, C(O)H, C(O)-R 10 C(O)-CH3, C(O)-CH2CH3, C(O)-CH2CH2CH3, C1-C5 linear or branched C(O)-haloalkyl, C(O)-CF3, -C(O)NH2, C(O)NHR, C(O)N(R) 10 )(R 11 ), C(O)N(CH3)2, SO2R, SO2N(R 10 )(R 11), SO2N(CH3)2, SO2NHC(O)CH3, C1-C5 linear or branched saturated or unsaturated alkyl, methyl, 2, 3, or 4-CH2-C6H4-Cl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl, benzyl, C1-C5 linear or branched saturated or unsaturated alkenyl, CH=C(Ph)2, C1-C5 linear or branched, or C3-C8 cyclic haloalkyl, CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2, C1-C5 linear or branched, or C3-C8 cyclic alkoxy, methoxy, ethoxy, propoxy, isopropoxy, O-CH2-cyclopropyl, O-cyclobutyl, O-cyclopentyl, O-cyclohexyl, 1-butoxy, 2-butoxy, O-tBu, C1-C5 linear or branched, or C3-C8 cyclic alkoxy (at least one methylene group (CH2) in the alkoxy is an oxygen source (substituted by), O-1-oxacyclobutyl, O-2-oxacyclobutyl, C1-C5 linear or branched thioalkoxy, C1-C5 linear or branched haloalkoxy, OCF3, OCHF2, C1-C5 linear or branched alkoxyalkyl, substituted or unsubstituted C3-C8 cycloalkyl (e.g., cyclopropyl, cyclopentyl), substituted or unsubstituted C3-C8 heterocyclic ring, 3-methyl-4H-1,2,4-triazole, 5-methyl-1,2,4-oxadiazole, Thiophene, oxazole, oxadiazole, imidazole, furan, triazole, tetrazole, pyridine (2, 3, or 4-pyridine), 3-methyl-2-pyridine, pyromidine, pyrazine, oxacyclobutane (1 or 2-oxacyclobutane), indole, protonated or deprotonated pyridine oxide, substituted or unsubstituted aryl, phenyl, substituted or unsubstituted benzyl, 4-Cl-benzyl, 4-OH-benzyl, each representing a distinct embodiment of the present invention. In some embodiments, R1' is H, C1-C5 linear or branched, unsubstituted alkyl, methyl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl, benzyl, C(O)-R 10, or C(O)-CH3, each representing a distinct embodiment according to the present invention. In some embodiments, each R1' is further substituted with at least one substitution selected from F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl (e.g., imidazole), C3-C8 cycloalkyl (e.g., cyclohexyl), CN, and NO2, each representing a distinct embodiment according to the present invention.

[0183] In some embodiments, R2 of compounds of formula I and / or I(a) to I(h) is H. In some embodiments, R2 is F, Cl, Br, or I, each representing a separate embodiment according to the present invention. In some embodiments, R2 is C(O)-R 10 And R 10 R2 is defined as follows: In some embodiments, R2 is C(O)-CH3. In some embodiments, R2 is a C1-C5 linear or branched, substituted or unsubstituted alkyl group. In some embodiments, R2 is a C1-C5 linear or branched, unsubstituted alkyl group. In some embodiments, R2 is methyl. In some embodiments, R2 is ethyl. In some embodiments, R2 is isopropyl. In some embodiments, R2' is methyl, 2, 3, or 4-CH2-C6H4-Cl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl, or benzyl, each representing a distinct embodiment according to the present invention. In some embodiments, R2 is OH, SH, R8-OH, CH2-OH, R8-SH, or -R8-OR 10-CH2-O-CH3, R8-(C3-C8 cycloalkyl), CH2-cyclohexyl, R8-(C3-C8 heterocyclic ring), CH2-imidazole, CH2-indazole, CD3, OCD3, CN, NO2, -CH2CN, -R8CN, NH2, NHR, N(R)2, R8-N(R 10 )(R 11 ), CH2-NH2, CH2-N(CH3)2, R9-R8-N(R 10 )(R 11 ), C≡C-CH2-NH2, B(OH)2, -OC(O)CF3, -OCH2Ph, NHC(O)-R 10 , NHC(O)CH3, NHC(O)-N(R 10 )(R 11 ), NHC(O)N(CH3)2, COOH, -C(O)Ph, C(O)OR 10 , C(O)O-CH3, C(O)O-CH(CH3)2, C(O)O-CH2CH3, R8-C(O)-R 10 , CH2C(O)CH3, C(O)H, C(O)-R 10 C(O)-CH3, C(O)-CH2CH3, C(O)-CH2CH2CH3, C1-C5 linear or branched C(O)-haloalkyl, C(O)-CF3, -C(O)NH2, C(O)NHR, C(O)N(R) 10 )(R 11 ), C(O)N(CH3)2, SO2R, SO2N(R 10 )(R 11), SO2N(CH3)2, SO2NHC(O)CH3, C1-C5 linear or branched saturated or unsaturated alkyl, methyl, 2, 3, or 4-CH2-C6H4-Cl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl, benzyl, C1-C5 linear or branched saturated or unsaturated alkenyl, CH=C(Ph)2, C1-C5 linear or branched, or C3-C8 cyclic haloalkyl, CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2, C1-C5 linear or branched, or C3-C8 cyclic alkoxy, methoxy, ethoxy, propoxy, isopropoxy, O-CH2-cyclopropyl, O-cyclobutyl, O-cyclopentyl, O-cyclohexyl, 1-butoxy, 2-butoxy, O-tBu, C1-C5 linear or branched, or C3-C8 cyclic alkoxy (at least one methylene group (CH2) in the alkoxy is an oxygen source (substituted by), O-1-oxacyclobutyl, O-2-oxacyclobutyl, C1-C5 linear or branched thioalkoxy, C1-C5 linear or branched haloalkoxy, OCF3, OCHF2, C1-C5 linear or branched alkoxyalkyl, substituted or unsubstituted C3-C8 cycloalkyl (e.g., cyclopropyl, cyclopentyl), substituted or unsubstituted C3-C8 heterocyclic ring, 3-methyl-4H-1,2,4-triazole, 5-methyl-1,2,4-oxadiazole, Thiophene, oxazole, oxadiazole, imidazole, furan, triazole, tetrazole, pyridine (2, 3, or 4-pyridine), 3-methyl-2-pyridine, pyromidine, pyrazine, oxacyclobutane (1 or 2-oxacyclobutane), indole, protonated or deprotonated pyridine oxide, substituted or unsubstituted aryl, phenyl, substituted or unsubstituted benzyl, 4-Cl-benzyl, 4-OH-benzyl, each representing a distinct embodiment of the present invention. In some embodiments, R2 is H, C1-C5 linear or branched, unsubstituted alkyl, methyl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl, benzyl, C(O)-R 10, or C(O)-CH3, each representing a distinct embodiment of the present invention. In some embodiments, R2 is further substituted with at least one substitution selected from F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl (e.g., imidazole), C3-C8 cycloalkyl (e.g., cyclohexyl), CN, and NO2, each representing a distinct embodiment of the present invention.

[0184] In some embodiments, R2' of compounds I and / or I(a) to I(h) is H. In some embodiments, R2' is F, Cl, Br, or I, each representing a separate embodiment according to the present invention. In some embodiments, R2' is C(O)-R 10 And R 10 R2' is defined as follows: In some embodiments, R2' is C(O)-CH3. In some embodiments, R2' is a C1-C5 linear or branched, substituted or unsubstituted alkyl group. In some embodiments, R2' is a C1-C5 linear or branched, unsubstituted alkyl group. In some embodiments, R2' is methyl. In some embodiments, R2' is ethyl. In some embodiments, R2' is isopropyl. In some embodiments, R2' is methyl, 2, 3, or 4-CH2-C6H4-Cl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl, or benzyl, each representing a distinct embodiment according to the present invention. In some embodiments, R2' is OH, SH, R8-OH, CH2-OH, R8-SH, or -R8-OR 10-CH2-O-CH3, R8-(C3-C8 cycloalkyl), CH2-cyclohexyl, R8-(C3-C8 heterocyclic ring), CH2-imidazole, CH2-indazole, CD3, OCD3, CN, NO2, -CH2CN, -R8CN, NH2, NHR, N(R)2, R8-N(R 10 )(R 11 ), CH2-NH2, CH2-N(CH3)2, R9-R8-N(R 10 )(R 11 ), C≡C-CH2-NH2, B(OH)2, -OC(O)CF3, -OCH2Ph, NHC(O)-R 10 , NHC(O)CH3, NHC(O)-N(R 10 )(R 11 ), NHC(O)N(CH3)2, COOH, -C(O)Ph, C(O)OR 10 , C(O)O-CH3, C(O)O-CH(CH3)2, C(O)O-CH2CH3, R8-C(O)-R 10 , CH2C(O)CH3, C(O)H, C(O)-R 10 C(O)-CH3, C(O)-CH2CH3, C(O)-CH2CH2CH3, C1-C5 linear or branched C(O)-haloalkyl, C(O)-CF3, -C(O)NH2, C(O)NHR, C(O)N(R) 10 )(R 11 ), C(O)N(CH3)2, SO2R, SO2N(R 10 )(R 11), SO2N(CH3)2, SO2NHC(O)CH3, C1-C5 linear or branched saturated or unsaturated alkyl, methyl, 2, 3, or 4-CH2-C6H4-Cl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl, benzyl, C1-C5 linear or branched saturated or unsaturated alkenyl, CH=C(Ph)2, C1-C5 linear or branched, or C3-C8 cyclic haloalkyl, CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2, C1-C5 linear or branched, or C3-C8 cyclic alkoxy, methoxy, ethoxy, propoxy, isopropoxy, O-CH2-cyclopropyl, O-cyclobutyl, O-cyclopentyl, O-cyclohexyl, 1-butoxy, 2-butoxy, O-tBu, C1-C5 linear or branched, or C3-C8 cyclic alkoxy (at least one methylene group (CH2) in the alkoxy is an oxygen source (substituted by), O-1-oxacyclobutyl, O-2-oxacyclobutyl, C1-C5 linear or branched thioalkoxy, C1-C5 linear or branched haloalkoxy, OCF3, OCHF2, C1-C5 linear or branched alkoxyalkyl, substituted or unsubstituted C3-C8 cycloalkyl (e.g., cyclopropyl, cyclopentyl), substituted or unsubstituted C3-C8 heterocyclic ring, 3-methyl-4H-1,2,4-triazole, 5-methyl-1,2,4-oxadiazole, Thiophene, oxazole, oxadiazole, imidazole, furan, triazole, tetrazole, pyridine (2, 3, or 4-pyridine), 3-methyl-2-pyridine, pyromidine, pyrazine, oxacyclobutane (1 or 2-oxacyclobutane), indole, protonated or deprotonated pyridine oxide, substituted or unsubstituted aryl, phenyl, substituted or unsubstituted benzyl, 4-Cl-benzyl, 4-OH-benzyl, each representing a distinct embodiment of the present invention. In some embodiments, R2' is H, C1-C5 linear or branched, unsubstituted alkyl, methyl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl, benzyl, C(O)-R 10, or C(O)-CH3, each representing a distinct embodiment according to the present invention. In some embodiments, R2' is further substituted with at least one substitution selected from F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl (e.g., imidazole), C3-C8 cycloalkyl (e.g., cyclohexyl), CN, and NO2, each representing a distinct embodiment according to the present invention.

[0185] In some embodiments, the R of compounds I, I(a) to I(c), I(g), and / or I(ga) 40 H is H. In some embodiments, R 40 is F, Cl, Br, or I, each representing a distinct embodiment according to the present invention. In some embodiments, R 40 C(O)-R 10 And R 10 It is defined as follows. In some embodiments, R 40 It is C(O)-CH3. In some embodiments, R 40 is a C1-C5 linear or branched, substituted or unsubstituted alkyl group. In some embodiments, R 40 R is a C1-C5 linear or branched, unsubstituted alkyl group. In some embodiments, R 40 is methyl. In some embodiments, R 40 is ethyl. In some embodiments, R 40 is isopropyl. In some embodiments, R 40 These are methyl, 2, 3, or 4-CH2-C6H4-Cl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl, and benzyl, each representing a distinct embodiment according to the present invention. In some embodiments, R 40These are OH, SH, R8-OH, CH2-OH, R8-SH, -R8-OR 10 -CH2-O-CH3, R8-(C3-C8 cycloalkyl), CH2-cyclohexyl, R8-(C3-C8 heterocyclic ring), CH2-imidazole, CH2-indazole, CD3, OCD3, CN, NO2, -CH2CN, -R8CN, NH2, NHR, N(R)2, R8-N(R 10 )(R 11 ), CH2-NH2, CH2-N(CH3)2, R9-R8-N(R 10 )(R 11 ), C≡C-CH2-NH2, B(OH)2, -OC(O)CF3, -OCH2Ph, NHC(O)-R 10 , NHC(O)CH3, NHC(O)-N(R 10 )(R 11 ), NHC(O)N(CH3)2, COOH, -C(O)Ph, C(O)OR 10 , C(O)O-CH3, C(O)O-CH(CH3)2, C(O)O-CH2CH3, R8-C(O)-R 10 , CH2C(O)CH3, C(O)H, C(O)-R 10 C(O)-CH3, C(O)-CH2CH3, C(O)-CH2CH2CH3, C1-C5 linear or branched C(O)-haloalkyl, C(O)-CF3, -C(O)NH2, C(O)NHR, C(O)N(R) 10 )(R 11 ), C(O)N(CH3)2, SO2R, SO2N(R 10 )(R 11), SO2N(CH3)2, SO2NHC(O)CH3, C1-C5 linear or branched saturated or unsaturated alkyl, methyl, 2, 3, or 4-CH2-C6H4-Cl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl, benzyl, C1-C5 linear or branched saturated or unsaturated alkenyl, CH=C(Ph)2, C1-C5 linear or branched, or C3-C8 cyclic haloalkyl, CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2, C1-C5 linear or branched, or C3-C8 cyclic alkoxy, methoxy, ethoxy, propoxy, isopropoxy, O-CH2-cyclopropyl, O-cyclobutyl, O-cyclopentyl, O-cyclohexyl, 1-butoxy, 2-butoxy, O-tBu, C1-C5 linear or branched, or C3-C8 cyclic alkoxy (at least one methylene group (CH2) in the alkoxy is an oxygen source (substituted by), O-1-oxacyclobutyl, O-2-oxacyclobutyl, C1-C5 linear or branched thioalkoxy, C1-C5 linear or branched haloalkoxy, OCF3, OCHF2, C1-C5 linear or branched alkoxyalkyl, substituted or unsubstituted C3-C8 cycloalkyl (e.g., cyclopropyl, cyclopentyl), substituted or unsubstituted C3-C8 heterocyclic ring, 3-methyl-4H-1,2,4-triazole, 5-methyl-1,2,4-oxadiazole, Thiofen, oxazole, oxadiazole, imidazole, furan, triazole, tetrazole, pyridine (2, 3, or 4-pyridine), 3-methyl-2-pyridine, pyromidine, pyrazine, oxacyclobutane (1 or 2-oxacyclobutane), indole, protonated or deprotonated pyridine oxide, substituted or unsubstituted aryl, phenyl, substituted or unsubstituted benzyl, 4-Cl-benzyl, 4-OH-benzyl, each representing a distinct embodiment of the present invention. In some embodiments, R 40 These include H, C1-C5 linear or branched, unsubstituted alkyl, methyl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl, benzyl, and C(O)-R 10, or C(O)-CH3, each representing a separate embodiment according to the present invention. In some embodiments, R 40 This is further substituted with at least one substitution selected from F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl (e.g., imidazole), C3-C8 cycloalkyl (e.g., cyclohexyl), CN, and NO2, each representing a distinct embodiment according to the present invention.

[0186] In some embodiments, R2 and R2' of compounds of formula I and I(a) to I(h) are the same. In some embodiments, both R2 and R2' are H. In some embodiments, both R2 and R2' are methyl. In some embodiments, R2 and R2' are different. In some embodiments, R2 is H and R2' is a C1-C5 linear or branched substituted or unsubstituted alkyl group. In some embodiments, R2 is H and R2' is methyl. In some embodiments, R2 is H and R2' is ethyl.

[0187] In some embodiments, R2 and R1 of formulas I and I(a) to I(h) (where n is 1 in some embodiments) are linked to form a C3-C8 substituted or unsubstituted, carbocyclic, or heterocyclic ring. In some embodiments, R2 and R1 are linked to form a C3-C8 carbocyclic ring (e.g., cyclopropane, cyclopentane, cyclohexane). In some embodiments, R2 and R1 are linked to form a C3-C8 heterocyclic ring.

[0188] In some embodiments, R3 of the compounds of formulas I, I(a), and I(h) is H, F, Cl, Br, I, OH, SH, =O, R8-OH, CH2-OH, R8-SH, -R8-OR 10 , CH2-O-CH3, CD3, OCD3, CN, NO2, -CH2CN, -R8CN, NH2, NHNH2, NHR, N(R)2, R8-N(R 10 )(R 11 )(For example, CH2-NH2, CH2-N(CH3)2), R9-R8-N(R 10 )(R 11 ), B(OH)2, -OC(O)CF3, -OCH2Ph, NHC(O)OBz, -NHC(O)-R 10 , NHC(O)CH3, NHC(O)-N(R 10 )(R 11 ), NHC(O)N(CH3)2, COOH, -C(O)Ph, C(O)OR 10 , C(O)O-CH3, C(O)O-CH2CH3, R8-C(O)-R 10 , CH2C(O)CH3, C(O)H, C(O)-R 10 C(O)-CH3, C(O)-CH2CH3, C(O)-CH2CH2CH3, C1-C5 linear or branched C(O)-haloalkyl, C(O)-CF3, -C(O)NH2, C(O)NHR, C(O)N(R) 10 )(R 11 ), C(O)N(CH3)2, SO2R, SO2N(R 10 )(R 11), SO2N(CH3)2, C1-C5 linear or branched, substituted or unsubstituted alkyl, methyl, C(OH)(CH3)(Ph), ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl, C1-C5 linear or branched, or C3-C8 cyclic haloalkyl, CF3, CF2CH3, CF2-cyclobutyl, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2, C1-C5 linear or branched, or C3-C8 cyclic alkoxy, methoxy, ethoxy, propoxy, isopropoxy, O-CH2-cyclopropyl, C1-C5 linear or branched thio These are xy, C1-C5 linear or branched haloalkoxy, C1-C5 linear or branched alkoxyalkyl, substituted or unsubstituted C3-C8 cycloalkyl, cyclopropyl, cyclopentyl, substituted or unsubstituted C3-C8 heterocyclic ring, 3-methyl-4H-1,2,4-triazole, 5-methyl-1,2,4-oxadiazole, thiophene, oxazole, isoxazole, imidazole, furan, triazole, pyridine (2,3, or 4-pyridine), pyrimidine, pyrazine, oxacyclobutane (1 or 2-oxacyclobutane), indole, substituted or unsubstituted aryl, or phenyl, each representing a distinct embodiment of the present invention.

[0189] In some embodiments, R3 of compounds of formulas I, I(a), I(b), I(c), I(e), I(g), I(ga), and I(h) is OH, F, SH, NH2, NHNH2, NHR, N(R)2, NHC(O)OBz, -NHC(O)-R 10R3 is (for example, NHC(O)CH3), a C1-C5 linear or branched, substituted or unsubstituted alkyl (for example, methyl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl), a substituted or unsubstituted C3-C8 cycloalkyl, a C1-C5 linear or branched, or a C3-C8 cyclic haloalkyl, a C1-C5 linear or branched, or a C3-C8 cyclic alkoxy, a substituted or unsubstituted C3-C8 heterocyclic ring, or a substituted or unsubstituted aryl, each representing a distinct embodiment of the present invention. In some embodiments, R3 is OH. In some embodiments, R3 is F. In some embodiments, R3 is F, Cl, Br, or I, each representing a distinct embodiment. In some embodiments, R3 is SH. In some embodiments, R3 is NH2. In some embodiments, R3 is NHNH2. In some embodiments, R3 is NHR. In some embodiments, R3 is N(R)2. In some embodiments, R3 is NHC(O)OBz. In some embodiments, R3 is -NHC(O)-R 10In some embodiments, R3 is NHC(O)CH3. In some embodiments, R3 is a C1-C5 linear or branched substituted or unsubstituted alkyl group. In some embodiments, R3 is methyl. In some embodiments, R3 is ethyl. In some embodiments, R3 is propyl. In some embodiments, R3 is isopropyl. In some embodiments, R3 is t-Bu. In some embodiments, R3 is isobutyl. In some embodiments, R3 is pentyl. In some embodiments, R3 is a substituted or unsubstituted C3-C8 cycloalkyl group. In some embodiments, R3 is a C1-C5 linear or branched, or C3-C8 cyclic haloalkyl group. In some embodiments, R3 is a C1-C5 linear or branched, or C3-C8 cyclic alkoxy group. In some embodiments, R3 is a substituted or unsubstituted C3-C8 heterocyclic ring. In some embodiments, R3 is a substituted or unsubstituted aryl group. In some embodiments, R3 of the compound of formula I(f) is SH, NHNH2, or NHC(O)OBz, each representing a distinct embodiment of the present invention. In some embodiments, R3 is further substituted with at least one substitution selected from F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl (e.g., imidazole), C3-C8 cycloalkyl (e.g., cyclohexyl), CN, and NO2, each representing a distinct embodiment of the present invention. In some embodiments, R3 of compounds of formulas I, I(a), I(b), I(c), I(e), I(g), I(ga), and / or I(h) is OH or NH2.

[0190] In some embodiments, R3 and R2 of any one compound of formulas I to I(h) are linked to form a C3-C8 substituted or unsubstituted, carbocyclic, or heterocyclic ring. In some embodiments, R3 and R2 are linked to form a C3-C8 carbocyclic ring. In some embodiments, R3 and R2 are linked to form a cyclopropyl ring. In some embodiments, R3 and R2 are linked to form a heterocyclic ring.

[0191] In some embodiments, R4 of the compounds of formula I, I(a), I(b), and / or I(f) is H, F, Cl, Br, I, OH, SH, =O, =NH-OH, R8-OH, CH2-OH, R8-SH, -R8-OR 10 , CH2-O-CH3, CD3, OCD3, CN, NO2, -CH2CN, -R8CN, NH2, NHNH2, NHR, N(R)2, R8-N(R 10 )(R 11 ), CH2-NH2, CH2-N(CH3)2, R9-R8-N(R 10 )(R 11 ), B(OH)2, -OC(O)CF3, -OCH2Ph, NHC(O)OBz, -NHC(O)-R 10 , NHC(O)H, NHC(O)CH3, NHC(O)-N(R 10 )(R 11 ), NHC(O)N(CH3)2, COOH, -C(O)Ph, C(O)OR 10 , C(O)O-CH3, C(O)O-CH2CH3, R8-C(O)-R 10 , CH2C(O)CH3, C(O)H, C(O)-R 10 C(O)-CH3, C(O)-CH2CH3, C(O)-CH2CH2CH3, C1-C5 linear or branched C(O)-haloalkyl, C(O)-CF3, -C(O)NH2, C(O)NHR, C(O)N(R) 10 )(R 11 ), C(O)N(CH3)2, SO2R, SO2N(R 10 )(R 11), SO2N(CH3)2, C1-C5 linear or branched, substituted or unsubstituted alkyl, methyl, C(OH)(CH3)(Ph), ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl, C1-C5 linear or branched, or C3-C8 cyclic haloalkyl, CF3, CF2CH3, CF2-cyclobutyl, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2, C1-C5 linear or branched, or C3-C8 cyclic alkoxy, methoxy, ethoxy, propoxy, isopropoxy, O-CH2-cyclopropyl, C1-C5 linear or branched thio Xy, C1-C5 linear or branched haloalkoxy, C1-C5 linear or branched alkoxyalkyl, substituted or unsubstituted C3-C8 cycloalkyl, cyclopropyl, cyclopentyl, substituted or unsubstituted C3-C8 heterocyclic ring, 3-methyl-4H-1,2,4-triazole, 5-methyl-1,2,4-oxadiazole, thiophene, oxazole, isoxazole, imidazole, furan, triazole, pyridine (2,3, or 4-pyridine), pyrimidine, pyrazine, oxacyclobutane (1 or 2-oxacyclobutane), indole, substituted or unsubstituted aryl, or phenyl, each representing a distinct embodiment of the present invention. In some embodiments, R4 is H. In some embodiments, R4 is =O. In some embodiments, R4 is =NH-OH. In some embodiments, R4 is NH2. In some embodiments, R4 is OH. In some embodiments, R4 is -NHC(O)-R 10In some embodiments, R4 is NHC(O)H. In some embodiments, R4 is NHC(O)CH3. In some embodiments, R4 of the compound is NHNH2. In some embodiments, R4 is alkyl. In some embodiments, R4 is methyl. In some embodiments, R4 is further substituted with at least one substitution selected from F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl (e.g., imidazole), C3-C8 cycloalkyl (e.g., cyclohexyl), CN, and NO2, each representing a distinct embodiment according to the present invention.

[0192] In some embodiments, R4 of compounds of formulas I to I(c) and / or I(e) to I(ga) is NH2, OH, NHNH2, NHR, N(R)2, -NHC(O)-R 10R4 is NHC(O)H, NHC(O)CH3, a C1-C5 linear or branched, substituted or unsubstituted alkyl, a C1-C5 linear or branched, or C3-C8 cyclic haloalkyl, a C1-C5 linear or branched, or C3-C8 cyclic alkoxy, a substituted or unsubstituted C3-C8 cycloalkyl, a substituted or unsubstituted C3-C8 heterocyclic ring, or a substituted or unsubstituted aryl, each representing a distinct embodiment of the present invention. In some embodiments, R4 is NH2. In some embodiments, R4 is OH. In some embodiments, R4 is alkyl. In some embodiments, R4 is methyl. In some embodiments, R4 is further substituted with at least one substitution selected from F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl (e.g., imidazole), C3-C8 cycloalkyl (e.g., cyclohexyl), CN, and NO2, each representing a distinct embodiment according to the present invention. In some embodiments, R4 of compounds of formulas I, I(a), I(b), I(c), I(e), I(g), I(ga), and / or I(f) is OH or NH2.

[0193] In some embodiments, if R3 of a compound of formulas I, I(a), I(b), I(c), I(e), I(g), I(ga) is OH, then R4 is NH2, and if R3 is NH2, then R4 is OH. In some embodiments, if R3 is OH and R4 is NH2, then n+m cannot be equal to 3. In some embodiments, both R3 and R4 cannot be NH2.

[0194] In some embodiments, R3 and R4 of compounds of formulas I, I(a) to I(c), I(e), I(g), and / or I(ga) are linked together to form ring A. In some embodiments, ring A has two chiral centers.

[0195] In some embodiments, ring A of formula I and / or I(e) is a substituted aryl. In some embodiments, ring A is 2-aminophenyl. In some embodiments, ring A is methyloxazolidine-2-one. In some embodiments, ring A is a substituted or unsubstituted cycloalkyl. In some embodiments, ring A is cyclopentyl. In some embodiments, ring A is cyclohexyl. In some embodiments, ring A is a substituted cycloalkyl. In some embodiments, the substitution is at least one selected from F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl, C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl, C3-C8 cycloalkyl, CN, and NO2, each representing a distinct embodiment according to the present invention. In some embodiments, ring A is a substituted cyclopropyl. In some embodiments, ring A is a substituted cyclobutyl. In some embodiments, ring A is a substituted cyclopentyl. In some embodiments, ring A is a substituted cyclohexyl. In some embodiments, ring A is substituted with at least NH2. In some embodiments, ring A is substituted with NH2. In some embodiments, ring A is a cycloalkyl that is substituted with at least NH2. In some embodiments, ring A is a cycloalkyl that is substituted with NH2. In some embodiments, ring A is a 5 or 6-membered nitrogen-containing heterocyclic ring. In some embodiments, ring A is a substituted or unsubstituted 1, 2, or 3-piperidine, oxazolidine-2-one, tetrahydropyrimidine, pyridine, dihydrothiazine, dihydroimidazole, tetrahydropyridine, or pyrrolidine, each of which is a separate embodiment of the present invention. In some embodiments, ring A is substituted with at least NH2. In some embodiments, R3 and R4 of formula I and / or I(e) are linked to form a 5 or 6-membered substituted or unsubstituted, aliphatic or aromatic, carbocyclic or heterocyclic ring.In some embodiments, R3 and R4 are linked to form a 5-membered unsubstituted, aliphatic heterocyclic ring. In some embodiments, R3 and R4 are linked to form a 6-membered unsubstituted, aliphatic heterocyclic ring. In some embodiments, R3 and R4 are linked to form a 5-membered substituted, aliphatic heterocyclic ring. In some embodiments, R3 and R4 are linked to form a methyloxazolidine-2-one. In some embodiments, R3 and R4 are linked to form a 6-membered substituted, aliphatic heterocyclic ring. In some embodiments, R3 and R4 are linked to form a 5-membered unsubstituted aromatic heterocyclic ring. In some embodiments, R3 and R4 are linked to form a 6-membered unsubstituted aromatic heterocyclic ring. In some embodiments, R3 and R4 are linked to form a 5-membered substituted, aromatic heterocyclic ring. In some embodiments, R3 and R4 are linked to form a 6-membered substituted, aromatic heterocyclic ring. In some embodiments, R3 and R4 are connected to form an allen.

[0196] In some embodiments, R3 and R4 of compounds of formulas I, I(a), I(b), I(e), I(g), and / or I(ga) are linked to form a ring A represented by the following structure, where R2 and R2' are as defined above.

[0197] [ka]

[0198] The wavy line in ring A above represents the rest of the molecule (i.e., -(C(R1)(R1')) in equations I~I(h)). n It is understood that this represents the connection point between A and ).

[0199] In some embodiments, R5 of the compounds of formulas I, I(a) to I(h), and / or X to X(d) is H, C1-C5 linear or branched, substituted or unsubstituted alkyl, methyl, CH2SH, ethyl, isopropyl, butyl, CH2-CCH, CH2-C(O)-OCH3, C2-C5 linear or branched, substituted or unsubstituted alkenyl, C2-C5 linear or branched, substituted or unsubstituted alkynyl, CCH, CH2-CCH, C1-C5 linear or branched haloalkyl, CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)-CH(CH3)2, R8-aryl, CH2-Ph, C(=CH2)-R 10R5 is C(=CH2)-C(O)-OCH3, C(=CH2)-CN, substituted or unsubstituted alkyl sulfone, SO2-CH2-cyclopentyl, substituted or unsubstituted aryl, phenyl, substituted or unsubstituted heteroaryl, pyridine (2, 3, and 4-pyridine), each representing a distinct embodiment of the present invention. In some embodiments, R5 is H, C1-C5 linear or branched substituted or unsubstituted alkyl, methyl, ethyl, isopropyl, butyl, CH2-CCH, CH2-C(O)-OCH3, C2-C5 linear or branched substituted or unsubstituted alkenyl, C2-C5 linear or branched substituted or unsubstituted alkynyl, CCH, CH2-CCH, C1-C5 linear or branched haloalkyl, substituted or unsubstituted alkyl sulfone, SO2-CH2-cyclopentyl, or substituted or unsubstituted aryl. In some embodiments, R5 is H. In some embodiments, R5 is a C1-C5 linear or branched substituted or unsubstituted alkyl group. In some embodiments, R5 is a C1-C5 linear alkyl group. In some embodiments, R5 is a branched C1-C5 alkyl group. In some embodiments, R5 is methyl. In some embodiments, R5 is ethyl. In some embodiments, R5 is butyl. In some embodiments, R5 is a substituted C1-C5 alkyl group. In some embodiments, R5 is a C1-C5 alkyl group substituted with a C2-C5 linear or branched alkynyl group. In some embodiments, R5 is CH2-CCH. In some embodiments, R5 is a C1-C5 alkyl group substituted with CCH. In some embodiments, R5 is CH2-C(O)-OCH3. In some embodiments, R5 is a substituted or unsubstituted alkyl sulfone. In some embodiments, R5 of compounds of formulas I, I(a) to I(h) is a substituted alkyl sulfone. In some embodiments, R5 of the compounds of formulas I, I(a) to I(h) is SO2-CH2-cyclopentyl.In some embodiments, R5 is further substituted with at least one substitution selected from F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl, C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl, C3-C8 cycloalkyl, CN, and NO2, each representing a distinct embodiment according to the present invention.

[0200] In some embodiments, the R of compounds of formula I(a), I(b), I(d), I(e), I(f), and / or I(h) 60 These are H, F, Cl, Br, I, OH, SH, R8-OH, R8-SH, -R8-OR 10 , CF3, CN, NO2, NH2, NHR, N(R)2, R8-N(R 10 )(R 11 ), -OC(O)CF3, -OCH2Ph, NHC(O)OBz, -NHC(O)-R 10 COOH, -C(O)Ph, C(O)OR 10 C(O)H, C(O)-R 10 , C1-C5 linear or branched C(O)-haloalkyl, -C(O)NH2, C(O)NHR, C(O)N(R 10 )(R 11 ), SO2R, SO2N(R 10 )(R 11 ), C1-C5 linear or branched saturated or unsaturated alkyl, C1-C5 linear or branched, or C3-C8 cyclic haloalkyl, C1-C5 linear or branched, or C3-C8 cyclic alkoxy, C1-C5 linear or branched thioalkoxy, C1-C5 linear or branched haloalkoxy, C1-C5 linear or branched alkoxyalkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C3-C8 heterocyclic ring, or substituted or unsubstituted aryl, each representing a separate embodiment of the present invention. In some embodiments, R 60 H is H. In some embodiments, R 60is COOH. In some embodiments, R 60 It does not exist (for example, when X4 is N). In some embodiments, R 60 The compound is further substituted with at least one substitution selected from F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl, C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl, C3-C8 cycloalkyl, CN, and NO2, each representing a distinct embodiment according to the present invention.

[0201] In some embodiments, the R of compounds of formula I(a), I(b), I(d), I(e), I(f), and / or I(h) 70 These are H, F, Cl, Br, I, OH, SH, R8-OH, R8-SH, -R8-OR 10 , CF3, CN, NO2, NH2, NHR, N(R)2, R8-N(R 10 )(R 11 ), -OC(O)CF3, -OCH2Ph, NHC(O)OBz, -NHC(O)-R 10 COOH, -C(O)Ph, C(O)OR 10 C(O)H, C(O)-R 10 , C1-C5 linear or branched C(O)-haloalkyl, -C(O)NH2, C(O)NHR, C(O)N(R 10 )(R 11 ), SO2R, SO2N(R 10 )(R 11 ), C1-C5 linear or branched, or C3-C8 cyclic haloalkyl, C1-C5 linear or branched, or C3-C8 cyclic alkoxy, C1-C5 linear or branched thioalkoxy, C1-C5 linear or branched haloalkyl, C1-C5 linear or branched alkoxyalkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C3-C8 heterocyclic ring, or substituted or unsubstituted aryl, each representing a separate embodiment of the present invention. In some embodiments, R 70is not alkyl. In some embodiments, R 70 The compound is further substituted with at least one substitution selected from F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl, C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl, C3-C8 cycloalkyl, CN, and NO2, each representing a distinct embodiment according to the present invention.

[0202] In some embodiments, the R of compounds of formula I(a), I(b), I(d), I(e), I(f), and / or I(h) 80 These are H, F, Cl, Br, I, OH, SH, R8-OH, R8-SH, -R8-OR 10 , CF3, CN, NO2, NH2, NHR, N(R)2, R8-N(R 10 )(R 11 ), -OC(O)CF3, -OCH2Ph, NHC(O)OBz, -NHC(O)-R 10 COOH, -C(O)Ph, C(O)OR 10 C(O)H, C(O)-R 10 , C1-C5 linear or branched C(O)-haloalkyl, -C(O)NH2, C(O)NHR, C(O)N(R 10 )(R 11 ), SO2R, SO2N(R 10 )(R 11 ), C1-C5 linear or branched saturated or unsaturated alkyl, C1-C5 linear or branched, or C3-C8 cyclic haloalkyl, C1-C5 linear or branched, or C3-C8 cyclic alkoxy, C1-C5 linear or branched thioalkoxy, C1-C5 linear or branched haloalkoxy, C1-C5 linear or branched alkoxyalkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C3-C8 heterocyclic ring, or substituted or unsubstituted aryl, each representing a separate embodiment of the present invention. In some embodiments, R 80 H is H. In some embodiments, R80 It does not exist (for example, when X6 is N). In some embodiments, R 80 The compound is further substituted with at least one substitution selected from F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl, C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl, C3-C8 cycloalkyl, CN, and NO2, each representing a distinct embodiment according to the present invention.

[0203] In some embodiments, the R of compounds of formula I(a), I(b), I(d), I(e), I(f), and / or I(h) 90 These are H, F, Cl, Br, I, OH, SH, R8-OH, R8-SH, -R8-OR 10 , CF3, CN, NO2, NH2, NHR, N(R)2, R8-N(R 10 )(R 11 ), -OC(O)CF3, -OCH2Ph, NHC(O)OBz, -NHC(O)-R 10 COOH, -C(O)Ph, C(O)OR 10 C(O)H, C(O)-R 10 , C1-C5 linear or branched C(O)-haloalkyl, -C(O)NH2, C(O)NHR, C(O)N(R 10 )(R 11 ), SO2R, SO2N(R 10 )(R 11 ), C1-C5 linear or branched saturated or unsaturated alkyl, C1-C5 linear or branched, or C3-C8 cyclic haloalkyl, C1-C5 linear or branched, or C3-C8 cyclic alkoxy, C1-C5 linear or branched thioalkoxy, C1-C5 linear or branched haloalkoxy, C1-C5 linear or branched alkoxyalkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C3-C8 heterocyclic ring, or substituted or unsubstituted aryl, each representing a separate embodiment of the present invention. In some embodiments, R 90H is H. In some embodiments, R 90 It does not exist (for example, when X7 is N). In some embodiments, R 90 The compound is further substituted with at least one substitution selected from F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl, C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl, C3-C8 cycloalkyl, CN, and NO2, each representing a distinct embodiment according to the present invention.

[0204] In some embodiments, if ring B of formulas I-I(b), I(e), I(f), or I(h) is present and R4 is NH2, then R3 cannot be OH. In some embodiments, if ring B of formulas I-I(b), I(e), I(f), or I(h) is present, then R3 is OH, R4 is NH2, and n cannot be 1. In some embodiments, if R3 is OH and R4 is NH2, then X1 or X7-R of the compound of formulas I-I(b), I(e), I(f), or I(h) 90 It cannot be CH.

[0205] In some embodiments, R8 in formulas I, I(a) to I(h), and / or X to X(d) is CH2. In other embodiments, R8 is CH2CH2. In other embodiments, R8 is CH2CH2CH2.

[0206] In some embodiments, p in formulas I, I(a) to I(h), and / or X to X(d) is 1. In other embodiments, p is 2. In other embodiments, p is 3.

[0207] In some embodiments, R9 in equations I, I(a) to I(h), and / or X to X(d) is C≡C.

[0208] In some embodiments, q in formulas I, I(a) to I(h), and / or X to X(d) is 2.

[0209] In some embodiments, R of formulas I, I(a) to I(h), and / or X to X(d) 10 In another embodiment, R 10 R is H, CN, C1-C5 linear or branched alkyl, methyl, ethyl, C(O)R, C(O)(OCH3), or S(O)2R, each representing a separate embodiment according to the present invention. In other embodiments, R 10 is a C1-C5 linear or branched alkyl group. In other embodiments, R 10 In other embodiments, R 10 In other embodiments, R 10 In other embodiments, R 10 In other embodiments, R 10 In other embodiments, R 10 In other embodiments, R 10 It is C(O)(OCH3).

[0210] In some embodiments, R of formulas I, I(a) to I(h), and / or X to X(d) 11 is a C1-C5 linear or branched alkyl group. In other embodiments, R 11 In another embodiment, R 11 R is H, CN, C1-C5 linear or branched alkyl, methyl, ethyl, C(O)R, C(O)(OCH3), or S(O)2R, each representing a separate embodiment according to the present invention. In other embodiments, R 11 In other embodiments, R 11 In other embodiments, R 11 In other embodiments, R 11 In other embodiments, R 11In other embodiments, R 11 In other embodiments, R 11 It is C(O)(OCH3).

[0211] In some embodiments, R of formulas I, I(a) to I(h), and / or X to X(d) 10 and R 11 These are linked to form a substituted or unsubstituted C3-C8 heterocyclic ring. In other embodiments, R 10 and R 11 These are linked to form a piperazine ring. In other embodiments, R 10 and R 11 These are linked to form a piperidine ring. In some embodiments, the ring is further substituted with at least one substitution selected from F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl, C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl, C3-C8 cycloalkyl, CN, and NO2, each representing a distinct embodiment according to the present invention.

[0212] In some embodiments, R in formulas I, I(a) to I(h), and / or X to X(d) is H. In other embodiments, R is a C1-C5 linear or branched alkyl, a C1-C5 linear or branched alkoxy, a phenyl, an aryl, or a heteroaryl. In other embodiments, R is not H. In other embodiments, R is a C1-C5 linear or branched alkyl. In other embodiments, R is methyl. In other embodiments, R is ethyl. In other embodiments, R is a C1-C5 linear or branched alkoxy. In other embodiments, R is methoxy. In other embodiments, R is phenyl. In other embodiments, R is aryl. In other embodiments, R is heteroaryl. In other embodiments, two gem R substituents are linked together to form a 5- or 6-membered heterocyclic ring.

[0213] In some embodiments, m in formulas I, I(a) to I(d), and I(f) to I(h) is 1. In some embodiments, m is 2. In some embodiments, m is 3, 4, or 5, each of which is a separate embodiment of the present invention.

[0214] In some embodiments, m in equations X(a) to X(d) is 1. In some embodiments, m is 2. In some embodiments, m is 3. In some embodiments, m is 1 or 2. In some embodiments, m is 1 or 3.

[0215] In some embodiments, n in formulas I and / or I(a) to I(h) is 0. In other embodiments, n is 1. In other embodiments, n is 2. In other embodiments, n is 3. In some embodiments, n is 4. In some embodiments, n is 5.

[0216] In some embodiments, n in formula X and / or X(a) to X(d) is 1. In some embodiments, n is 2. In some embodiments, n is 0. In some embodiments, n is 3. In some embodiments, n is 1 or 2. In some embodiments, n is 0 or 1. In some embodiments, n is 0 to 2.

[0217] In some embodiments, o in formula X(a) is 1. In some embodiments, o is 2. In some embodiments, o is 0. In some embodiments, o is 3. In some embodiments, o is 1 or 2. In some embodiments, o is 0 or 1. In some embodiments, o is 0 to 2.

[0218] In some embodiments, X1 in formulas I, I(a) to I(d), and I(f) to I(h) is S. In other embodiments, X1 is O. In other embodiments, X1 is CH2. In some embodiments, X1 in formulas I, I(a), I(c), I(d), and I(f) to I(h) is N-OH. In some embodiments, X1 is C(R)2. In some embodiments, X1 is N-OMe.

[0219] In some embodiments, X1 in formulas X~X(c) is S. In other embodiments, X1 is O. In other embodiments, X1 is CH2. In some embodiments, X1 is CH(R). In some embodiments, X1 is C(R)2. In some embodiments, X1 is S, O, or CH2.

[0220] In some embodiments, X2 in formulas I, I(a) to I(d), and I(g) is S. In other embodiments, X2 is O. In other embodiments, X2 is CH2. In some embodiments, X2 in formulas I, I(a), I(c), I(d), and I(f) to I(h) is N-OH. In some embodiments, X2 is C(R)2. In some embodiments, X2 is N-OMe.

[0221] In some embodiments, X2 in formula I is O, and R3 or R4 is NH2.

[0222] In some embodiments, X2 in formulas X, X(b), X(c), and / or X(d) is S. In other embodiments, X2 is O. In other embodiments, X2 is CH2. In some embodiments, X2 is CH(R). In some embodiments, X2 is C(R)2. In some embodiments, X2 is S, O, or CH2.

[0223] In some embodiments, X1 and X2 of the compounds of formulas X to X(d) are both CH2.

[0224] In some embodiments, X2 in compounds of formulas I, I(a), I(b), I(f), and / or I(h) is linked with the carbon adjacent to X1 to form ring B represented by the following structure (in which case X1 is X7),

[0225] [ka]

[0226] In the formula, X4, X5, X6, and X7 are each independently C or N, and if any of X4, X5, X6, and X7 is N, then each substitution R 90 , R 60 , R 70 , or R 80 However, it does not exist, R 90, R 60 , R 70 , or R 80 However, this is as defined above.

[0227] In some embodiments, X3 in formulas I and / or I(a) to I(h) is O. In other embodiments, X3 is NH. In other embodiments, X3 is NR 50 In other embodiments, X3 is S.

[0228] In some embodiments, formula I and / or I(a) to I(h) 50 H is H. In some embodiments, R 50 is a C1-C5 linear or branched, substituted or unsubstituted alkyl group. In some embodiments, R 50 is methyl. In some embodiments, R 50 is ethyl. In some embodiments, R 50 is butyl. In some embodiments, R 50 is i-propyl. In some embodiments, R 50 The compound is further substituted with at least one substitution selected from F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl, C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, linear, branched, or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl, C3-C8 cycloalkyl, CN, and NO2, each representing a distinct embodiment according to the present invention.

[0229] In some embodiments, X4 in formulas I, I(a) to I(d), and I(f) to I(h) is C. In other embodiments, X4 is N.

[0230] In some embodiments, X5 in formulas I, I(a) to I(d), and I(f) to I(h) is C. In other embodiments, X5 is N.

[0231] In some embodiments, X6 in formulas I, I(a) to I(d), and I(f) to I(h) is C. In other embodiments, X6 is N.

[0232] In some embodiments, X7 in formulas I, I(a) to I(d), and I(f) to I(h) is C. In other embodiments, X7 is N.

[0233] In some embodiments, if any of X4, X5, X6, and X7 is N, then each substitution R 90 , R 60 , R 70 , or R 80 It does not exist.

[0234] In some embodiments, ring A of the compound of formula X is a C5-C7 cycloalkyl group. In some embodiments, ring A is a cyclohexyl group. In some embodiments, ring A is a cyclopropyl group. In some embodiments, ring A is a cyclobutyl group. In some embodiments, ring A is absent.

[0235] In some embodiments, ring B of the compound of formula X is a 5- to 7-membered nitrogen-containing heterocyclic ring. In some embodiments, ring B is pyrrolidine. In some embodiments, ring B is piperidine. In some embodiments, ring B is absent.

[0236] In some embodiments, ring C of the compound of formula X is a C5-C7 substituted or unsubstituted cycloalkyl group. In some embodiments, ring C is an unsubstituted cycloalkyl group. In some embodiments, ring C is a substituted cycloalkyl group. In some embodiments, ring C is a cyclopentyl group. In some embodiments, ring C is a cyclohexyl group. In some embodiments, ring C is an aromatic ring. In some embodiments, ring C is a phenyl group. In some embodiments, ring C is absent.

[0237] In some embodiments, ring D of the compound of formula X is a C5-C7 cycloalkyl group. In some embodiments, ring D is a cyclopentyl group. In some embodiments, ring D is absent.

[0238] In some embodiments, ring E of the compound of formula X is a substituted or unsubstituted 5- to 7-membered nitrogen-containing heterocyclic ring. In some embodiments, ring E is a substituted 5- to 7-membered nitrogen-containing heterocyclic ring. In some embodiments, ring E is an unsubstituted 5- to 7-membered nitrogen-containing heterocyclic ring. In some embodiments, ring E is a pyrrolidine. In some embodiments, ring E is a piperidine. In some embodiments, ring E is an oxazolidine-2-one. In some embodiments, E is a substituted oxazolidine-2-one. In some embodiments, ring E is absent.

[0239] In some embodiments, at least one of the rings A to E of the compound of formula (X) is not absent. In some embodiments, only one of the rings A to E is not absent. In some embodiments, all of the rings A to E of the compound of formula (X) are absent.

[0240] In various embodiments, the present invention relates to one of the compounds presented in Table 1 above, a pesticide composition, and / or a method of using the same for controlling undesirable plant growth.

[0241] In various embodiments, the present invention relates to the use of any one of the compounds presented in Table 2 herein and / or a pesticide composition thereof for controlling undesirable plant growth.

[0242] It is well understood that in the structures presented in the present invention, where carbon atoms are bonded with fewer than four atoms, the presence of hydrogen atoms satisfies all the valencies of carbon. It is also well understood that in the structures presented in the present invention, where nitrogen atoms are bonded with fewer than three atoms, the presence of hydrogen atoms satisfies all the valencies of nitrogen.

[0243] In some embodiments, the present invention relates to compounds, pesticide compositions, and / or methods of use thereof as listed above herein, wherein the compounds are pesticide-acceptable salts, stereoisomers, optical isomers, tautomers, hydrates, N-oxides, reverse amide analogs, isotopic variants (deuterated analogs), or any combination thereof. In some embodiments, the compounds are herbicides. In some embodiments, the compounds control undesirable plant growth.

[0244] As used herein, “single or condensed aromatic ring system or heteroaromatic ring system” means phenyl, naphthyl, pyridinyl, (2-, 3-, and 4-pyridinyl), quinolinyl, pyrimidinyl, pyridadinyl, pyrazinyl, triazinyl, tetradinyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, imidazolyl, 1-methylimidazole, pyrazolyl, pyrrolyl, furanyl, thiophenyl, quinolinyl, isoquinolinyl, 2,3-dihydroindenyl, indenyl, tetrahydronaphthyl, 3,4-dihydro-2H- Benzo[b][1,4]dioxepin, benzodioxolil, benzo[d][1,3]dioxol, tetrahydronaphthyl, indolyl, 1H-indole, isoindolyl, anthracenyl, benzimidazolyl, 2,3-dihydro-1H-benzo[d]imidazolyl, indazolyl, 2H-indazole, triazolyl, 4,5,6,7-tetrahydro-2H-indazole, 3H-indole-3-one, prinyl, benzoxazolyl, 1,3-benzoxazolyl, benzoisoxazolyl, benzothiazolyl, 1,3-benzothiazo Lu, 4,5,6,7-tetrahydro-1,3-benzothiazole, quinazolinil, quinoxalinil, 1,2,3,4-tetrahydroquinoxaline, 1-(pyridine-1(2H)-yl)etanone, cinnolinil, phthalazinil, quinolinil, isoquinolinil, acridinil, benzofuranil, 1-benzofuran, isobenzofuranil, benzofuran-2(3H)-one, benzothiophenyl, benzoxadiazole, benzo[c][1,2,5]oxadiazolyl, benzo[c]thiophenyl, benzodioxolil, thiadiazolyl, [1,3]ox Sazolo[4,5-b]pyridine, oxadiadiol, imidazo[2,1-b][1,3]thiazole, 4H,5H,6H-cyclopenta[d][1,3]thiazole, 5H,6H,7H,8H-imidazo[1,2-a]pyridine, 7-oxo-6H,7H-[1,3]thiazolo[4,5-d]pyrimidine, [1,3]thiazolo[5,4-b]pyridine, 2H,3H-imidazo[2,1-b][1,3]thiazole, thieno[3,2-d]pyrimidine-4(3H)-one, 4-oxo-4H-thieno[3,2-d][1,3]thiazine, imidazo[1,2-a]pyridine, 1H-imidazo[4,5-b]pyridine, 1H-imidazo[4,5-c]pyridine, 3H-imidazo[4,5-c]pyridine, pyrazolo[1,5-a]pyridine, imidazo[1,2-a]pyrazine, imidazo[1,2-a]pyrimidine, 1H-pyrrolo[2,3-b]pyridine, pyrido[2,3-b]pyrazine, pyrido[2,3-b]pyrazine-3(4H)-one, 4H-thieno[3,2-b]pyrrole, quinone This includes, but is not limited to, xaline-2(1H)-one, 1H-pyrrolo[3,2-b]pyridine, 7H-pyrrolo[2,3-d]pyrimidine, oxazolo[5,4-b]pyridine, thiazolo[5,4-b]pyridine, thieno[3,2-c]pyridine, 3-methyl-4H-1,2,4-triazole, 5-methyl-1,2,4-oxadiazole, methyloxazolidine-2-one, and any other such ring.

[0245] As used herein, the term "alkyl" can refer to any linear or branched alkyl group containing up to approximately 30 carbon atoms unless otherwise specified. In various embodiments, the alkyl group contains C1-C5 carbon atoms. In some embodiments, the alkyl group contains C1-C6 carbon atoms. In some embodiments, the alkyl group contains C1-C8 carbon atoms. In some embodiments, the alkyl group contains C2-C5 carbon atoms. In some embodiments, the alkyl group contains C2-C8 carbon atoms. In some embodiments, the alkyl group contains C1-C 10 Contains carbon. In some embodiments, the alkyl is C1-C 12 It is carbon. In some embodiments, alkyl is C1-C 20It is carbon. In some embodiments, a branched alkyl is an alkyl substituted with an alkyl side chain of 1 to 5 carbon atoms. In various embodiments, the alkyl may be unsubstituted. In some embodiments, the alkyl may be substituted with halogens, haloalkyls, hydroxyls, alkoxys, carbonyls, amides, alkylamides, dialkylamides, cyanos, nitros, CO2H, aminos, alkylaminos, dialkylaminos, carboxyls, thios, thioalkyls, C1-C5 linear or branched haloalkoxys, CF3, phenyls, halophenyls, (benzyloxy)phenyls, -CH2CN, NH2, NH-alkyls, N(alkyl)2, -OC(O)CF3, -OCH2Ph, -NHC(O)-alkyls, -C(O)Ph, C(O)O-alkyls, C(O)H, -C(O)NH2, or any combination thereof.

[0246] Alkyl groups can be single substituents or components of larger substituents such as alkoxy, alkoxyalkyl, haloalkyl, arylalkyl, alkylamino, dialkylamino, alkylamide, and alkylurea. Preferred alkyl groups are methyl, ethyl, and propyl, and therefore include halomethyl, dihalomethyl, trihalomethyl, haloethyl, dihaloethyl, trihaloethyl, halopropyl, dihalopropyl, trihalopropyl, methoxy, ethoxy, propoxy, arylmethyl, arylethyl, arylpropyl, methylamino, ethylamino, propylamino, dimethylamino, diethylamino, methylamide, acetamide, propylamide, halomethylamide, haloethylamide, halopropylamide, methylurea, ethylurea, propylurea, 2, 3, or 4-CH2-C6H4-Cl,C(OH)(CH3)(Ph).

[0247] As used herein, the term “alkenyl” can be any linear or branched alkenyl group containing up to about 30 carbon atoms and at least one carbon-carbon double bond, as defined herein above for the term “alkyl.” Thus, the term alkenyl as defined herein also includes alkadienes, alkatrienes, alkatetraenes, and the like. In some embodiments, the alkenyl group contains one carbon-carbon double bond. In some embodiments, the alkenyl group contains two, three, four, five, six, seven, or eight carbon-carbon double bonds, each representing a distinct embodiment according to the present invention. Non-limiting examples of alkenyl groups include ethenyl, propenyl, butenyl (i.e., 1-butenyl, trans-2-butenyl, cis-2-butenyl, and isobutyrenyl), pentene (i.e., 1-pentenyl, cis-2-pentenyl, and trans-2-pentenyl), and hexene (e.g., 1-hexenyl, (E)-2-hexenyl, (Z)-2-hexenyl, (E)-3-hexenyl, (Z)-3-hexenyl, 2-methyl-1-pentene, etc.), all of which may be substituted as defined herein above for the term "alkyl".

[0248] As used herein, the term “alkynyl” can be any linear or branched alkynyl group containing up to about 30 carbon atoms and at least one carbon-carbon triple bond, as defined herein above for the term “alkyl”. Thus, the term alkynyl as defined herein also includes alkadiynes, alkatolynes, alkatetraynes, and the like. In some embodiments, the alkynyl group contains one carbon-carbon triple bond. In some embodiments, the alkynyl group contains two, three, four, five, six, seven, or eight carbon-carbon triple bonds, each representing a distinct embodiment according to the present invention. Non-limiting examples of alkynyl groups include acetylenyl, propynyl, butynyl (i.e., 1-butynyl, 2-butynyl, and isobutylinyl), pentine (i.e., 1-pentynyl, 2-pentynyl), and hexine (e.g., 1-hexynyl, 2-hexynyl, 3-hexynyl, etc.), all of which may be substituted as defined herein above for the term "alkyl".

[0249] As used herein, the term “aryl” refers to any aromatic ring that is directly bonded to another group and may be either substituted or unsubstituted. An aryl group may also be a single substituent or it may be a component of a larger substituent such as an arylalkyl, arylamino, or arylamide. Exemplary aryl groups include, but are not limited to, phenyl, tolyl, xylyl, furanyl, naphthyl, pyridinyl, pyrimidinyl, pyridadinyl, pyrazinyl, triazinyl, thiazolyl, oxazolyl, isoxazolyl, pyrazolyl, imidazolyl, thiophenyl, pyrrolyl, indolyl, phenylmethyl, phenylethyl, phenylamino, phenylamide, 3-methyl-4H-1,2,4-triazolyl, 5-methyl-1,2,4-oxadiazolyl, and others. Substitutions include, but are not limited to, F, Cl, Br, I, C1-C5 linear or branched alkyl, C1-C5 linear or branched haloalkyl, C1-C5 linear or branched alkoxy, C1-C5 linear or branched haloalkoxy, CF3, phenyl, halophenyl, (benzyloxy)phenyl, CN, NO2, -CH2CN, NH2, NH-alkyl, N(alkyl)2, hydroxyl, -OC(O)CF3, -OCH2Ph, -NHC(O)-alkyl, COOH, -C(O)Ph, C(O)O-alkyl, C(O)H, -C(O)NH2, or any combination thereof.

[0250] As used herein, the term "alkoxy" refers to an ether group substituted with an alkyl group as defined above. Alkoxy refers to both linear and branched alkoxy groups. Non-exclusive examples of alkoxy groups include methoxy, ethoxy, propoxy, iso-propoxy, and tert-butoxy.

[0251] The “haloalkyl” group refers to an alkyl group as defined above, which in some embodiments is substituted with one or more halogen atoms, such as F, Cl, Br, or I. The term “haloalkyl” includes, but is not limited to, fluoroalkyl groups, i.e., alkyl groups having at least one fluorine atom. Non-limiting examples of haloalkyl groups are CF3, CF2CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, and CF(CH3)-CH(CH3)2.

[0252] In some embodiments, the "halophenyl" group refers to a phenyl substituent substituted with one or more halogen atoms, such as F, Cl, Br, or I. In one embodiment, the halophenyl is 4-chlorophenyl.

[0253] The “alkoxyalkyl” group refers to an alkyl group as defined above, which in some embodiments is substituted with an alkoxy group as defined above, such as methoxy, ethoxy, propoxy, i-propoxy, t-butoxy, etc. Non-limiting examples of alkoxyalkyl groups are -CH2-O-CH3, -CH2-O-CH(CH3)2, -CH2-OC(CH3)3, -CH2-CH2-O-CH3, -CH2-CH2-O-CH(CH3)2, and -CH2-CH2-OC(CH3)3.

[0254] A "cycloalkyl" or "carbocyclic" group refers to a ring structure containing carbon atoms as ring atoms in various embodiments, and can be saturated or unsaturated, substituted or unsubstituted, monochromatic or condensed. In some embodiments, the cycloalkyl is a 3- to 10-membered ring. In some embodiments, the cycloalkyl is a 3- to 12-membered ring. In some embodiments, the cycloalkyl is a 6-membered ring. In some embodiments, the cycloalkyl is a 5- to 7-membered ring. In some embodiments, the cycloalkyl is a 3- to 8-membered ring. In some embodiments, the cycloalkyl group may be unsubstituted or substituted with halogens, alkyl, haloalkyl, hydroxyl, alkoxy, carbonyl, amide, alkylamide, dialkylamide, cyano, nitro, CO2H, amino, alkylamino, dialkylamino, carboxyl, thio, thioalkyl, C1-C5 linear or branched haloalkoxy, CF3, phenyl, halophenyl, (benzyloxy)phenyl, -CH2CN, NH2, NH-alkyl, N(alkyl)2, -OC(O)CF3, -OCH2Ph, -NHC(O)-alkyl, -C(O)Ph, C(O)O-alkyl, C(O)H, -C(O)NH2, or any combination thereof. In some embodiments, the cycloalkyl ring may be condensed to another saturated or unsaturated cycloalkyl or heterocyclic 3- to 8-membered ring. In some embodiments, the cycloalkyl ring is a saturated ring. In some embodiments, the cycloalkyl ring is an unsaturated ring. Non-exclusive examples of cycloalkyl groups include cyclohexyl, cyclohexenyl, cyclopropyl, cyclopropenyl, cyclopentyl, cyclopentenyl, cyclobutyl, cyclobutenyl, cyclooctyl, cyclooctadienyl (COD), and cyclooctane (COE).

[0255] A "heterocyclic" or "heterocyclic" group, in various embodiments, refers to a ring structure that, in addition to carbon atoms, includes sulfur, oxygen, nitrogen, or any combination thereof as part of the ring. An "aromatic heterocyclic" group, in various embodiments, refers to an aromatic ring structure that, in addition to carbon atoms, includes sulfur, oxygen, nitrogen, selenium, or any combination thereof as part of the ring. In some embodiments, the heterocyclic or aromatic heterocyclic is a 3- to 10-membered ring. In some embodiments, the heterocyclic or aromatic heterocyclic is a 3- to 12-membered ring. In some embodiments, the heterocyclic or aromatic heterocyclic is a 6-membered ring. In some embodiments, the heterocyclic or aromatic heterocyclic is a 5- to 7-membered ring. In some embodiments, the heterocyclic or aromatic heterocyclic is a 3- to 8-membered ring. In some embodiments, the heterocyclic group or aromatic heterocycle may be unsubstituted or substituted with halogens, alkyl, haloalkyl, hydroxyl, alkoxy, carbonyl, amide, alkylamide, dialkylamide, cyano, nitro, CO2H, amino, alkylamino, dialkylamino, carboxyl, thiol, thioalkyl, C1-C5 linear or branched haloalkoxy, CF3, phenyl, halophenyl, (benzyloxy)phenyl, -CH2CN, NH2, NH-alkyl, N(alkyl)2, -OC(O)CF3, -OCH2Ph, -NHC(O)-alkyl, -C(O)Ph, C(O)O-alkyl, C(O)H, -C(O)NH2, or any combination thereof. In some embodiments, the heterocycle or aromatic heterocycle may be condensed to another saturated or unsaturated cycloalkyl or heterocyclic 3- to 8-membered ring. In some embodiments, the heterocyclic ring is a saturated ring. In some embodiments, the heterocyclic ring is an unsaturated ring.Non-limiting examples of heterocyclic rings or aromatic heterocyclic systems include pyridine, piperidine, morpholine, piperazine, thiophene, pyrrole, benzodioxole, benzofuran-2(3H)-one, benzo[d][1,3]dioxole, indole, oxazole, isoxazole, imidazole and 1-methylimidazole, furan, triazole, pyrimidine, pyrazine, oxacyclobutane (1 or 2-oxacyclobutane), naphthalene, tetrahydrothiophene 1,1-dioxide, thiazole, benzimidazole, piperidine, 1-methylpiperine, isoquinoin, 1,3-dihydrobenzofuran, benzofuran, 3-methyl-4H-1,2,4-triazole, 5-methyl-1,2,4-oxadiazole, oxazolidine-2-one, methyloxazolidine-2-one, or indole, each of which is a separate embodiment according to the present invention.

[0256] In various embodiments, the present invention provides the compound of the present invention, or pesticide-acceptable salts, stereoisomers, optical isomers, tautomers, hydrates, N-oxides, reverse amide analogs, isotopic variants (e.g., deuterated analogs), or any combination thereof. In various embodiments, the present invention provides a single stereoisomer of the compound of the present invention. In some embodiments, the present invention provides an optical isomer of the compound of the present invention. In some embodiments, the present invention provides a pesticide-acceptable salt of the compound of the present invention. In some embodiments, the present invention provides a tautomer of the compound of the present invention. In some embodiments, the present invention provides a hydrate of the compound of the present invention. In some embodiments, the present invention provides an N-oxide of the compound of the present invention. In some embodiments, the present invention provides a reverse amide analog of the compound of the present invention. In some embodiments, the present invention provides isotopic variants (including, but not limited to, deuterated analogs) of the compound of the present invention. In some embodiments, the present invention provides polymorphs of the compound of the present invention. In some embodiments, the present invention provides crystals of the compound of the present invention. In some embodiments, the present invention provides pesticide compositions comprising any combination of the compounds of the present invention described herein, or, in some embodiments, stereoisomers, optical isomers, pesticide-acceptable salts, tautomers, hydrates, N-oxides, isotopic variants (deuterated analogs), polymorphs, or crystals of the compounds of the present invention.

[0257] In various embodiments, the term "isomer" includes, but is not limited to, stereoisomers, including optical isomers and analogs, structural isomers and analogs, conformational isomers and analogs, etc. In some embodiments, the isomer is a stereoisomer. In other embodiments, the isomer is an optical isomer.

[0258] In various embodiments, the present invention encompasses the use of various stereoisomers of the compounds of the present invention. Those skilled in the art will understand that the compounds of the present invention may contain at least one chiral center. Thus, the compounds used in the methods of the present invention may exist in an optically active form or a racemic form and may be isolated thereto. The compounds according to the present invention may also exist as stereoisomers, enantiomer concentrates, racemic mixtures, or single diastereomers, diastereomer mixtures, or other stereoisomers, and may include, but are not limited to, (R)(R), (R)(S), (S)(S), (S)(R), (R)(R)(R), (R)(R)(S), (R)(S)(R), (R)(S)(R), (R)(S)(S), (S)(R)(R), (S)(R)(S), (S)(S)(R), or (S)(S)(S) stereoisomers. Some compounds may also exhibit pleomorphism. It should be understood that the present invention encompasses any racemic, optically active, pleomorphic, or stereoisomeric form, or mixtures thereof, and these forms possess properties useful for controlling various undesirable plant growths, as described herein.

[0259] The methods for preparing the optically active form are well known (for example, by recrystallization techniques to separate the racemic form, by synthesis from optically active starting materials, by chiral synthesis, or by chromatographic separation using a chiral stationary phase).

[0260] The compounds of the present invention can also exist in the form of a racemic mixture containing substantially equal amounts of stereoisomers. In some embodiments, the compounds of the present invention can be prepared using known procedures or otherwise isolated to obtain stereoisomers that are substantially free of their corresponding stereoisomers (i.e., substantially pure). By substantially pure, the stereoisomers are intended to be at least about 95% pure, more preferably at least about 98% pure, and most preferably at least about 99% pure.

[0261] The compounds of the present invention may also exist in the form of hydrates, meaning that the compounds further contain a stoichiometric or non-stoichiometric amount of water bonded by non-covalent intermolecular forces.

[0262] As used herein, when several chemical functional groups (e.g., alkyl or aryl) are said to be "substituted," it is defined herein that one or more substitutions are possible.

[0263] The compounds of the present invention may exist in the form of one or more possible tautomers, and depending on the conditions, it may be possible to separate some or all of the tautomers into individual distinct entities. It should be understood that all possible tautomers, including all additional enol and keto tautomers and / or isomers, are covered herein. For example, the following tautomers are included, but are not limited to:

[0264] [ka]

[0265] Tautomerization of the pyrazolone ring:

[0266] [ka]

[0267] The present invention comprises “pesticide-acceptable salts” of the compounds of the present invention, which can be produced by reaction of the compounds of the present invention with acids or bases. Certain compounds, particularly those having acidic or basic groups, can also be in the form of salts, preferably pesticide-acceptable salts. The term “pesticide-acceptable salts” refers to those salts that retain the pesticide efficacy and properties of the free base or free acid, without being pesticideally or otherwise undesirable. Salts are produced by inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, and phosphoric acid, and by organic acids such as acetic acid, propionic acid, glycolic acid, pyruvic acid, oxalic acid, maleic acid, malonic acid, succinic acid, fumaric acid, tartaric acid, citric acid, benzoic acid, cinnamic acid, mandelic acid, methanesulfonic acid, ethanesulfonic acid, p-toluenesulfonic acid, salicic acid, and N-acetylcysteine. Other salts are known to those skilled in the art and can be readily adapted for use according to the present invention.

[0268] Suitable pesticide-acceptable salts of the amines of the compounds of the present invention can be prepared from inorganic or organic acids. In various embodiments, examples of inorganic salts of the amines include bisulfates, borates, bromides, chlorides, hemisulfates, hydrobroms, hydrochlorides, 2-hydroxyethyl sulfonate (hydroxyethane sulfonate), iodates, iodides, isothionates, nitrates, persulfates, phosphates, sulfates, sulfamates, sulfanilates, sulfonic acids (alkyl sulfonates, aryl sulfonates, halogen-substituted alkyl sulfonates, halogen-substituted aryl sulfonates), sulfonates, and thiocyanates.

[0269] In various embodiments, examples of organic salts of amines may be selected from organic acids of the aliphatic, alicyclic, aromatic, aromaticaliphatic, heterocyclic, carboxylic acid, and sulfonic acid classes, examples of which include acetate, aspartate, ascorbate, adipine, anthranilate, algeneate, alkanecarboxylate, substituted alkanecarboxylate, alginate, benzenesulfonate, benzoate, bisulfate, butyrate, bicarbonate, tartrate, citrate, camphorate, camphorsulfonate, cyclohexylsulfamate, cyclopentanepropionate, and edetate. Cinnamal, cinnamate, carbonate, clavulanate, cinnamate, dicarboxylate, digluconate, dodecylsulfonate, dihydrochloride, decanoate, enantic acid, ethanesulfonic acid, edetic acid, edicyl acid, estrulate, esylate, fumarate, formate, fluoride, galacturonic acid, gluconate, glutamate, glycolate, gluconate, glucoheptanate, glycerophosphate, gluceptate, glycolyl arsanylate, glutarate, glutamate, heptanoic acid, hexanoate, hydroxymaleate, hydroxycarboxylic acid, Hexylresorcinate, hydroxybenzoate, hydroxynaphthoate, hydrofluoric acid, lactate, lactobionate, laurate, malate, maleate, methylenebis(β-oxynaphthoate), malonate, mandelate, mesylate, methanesulfonate, methyl bromide, methyl nitrate, methylsulfonate, monopotassium maleate, mucinate, monocarboxylate, naphthalenesulfonate, 2-naphthalenesulfonate, nicotinate, nitrate, napsylate, N-methylglucamine, oxalate, octanoate, oleate, pa Moates, phenylacetates, picates, phenylbenzoates, pivalates, propions, phthalates, phenylacetates, pectinates, phenylpropions, palmitates, pantothenates, polygalacturonic acid, pyruvates, quinates, salicylates, succinates, stearates, sulfanilates, basic acetates, tartrates, theophylline acetates, p-toluenesulfonates (tosylates), trifluoroacetates, terephthalates, tannates, theoclates, trihaloacetates, triethiozides, tricarboxylates, undecanoates,And it may be selected from valerates.

[0270] In various embodiments, examples of inorganic salts of carboxylic acids or hydroxyls may be selected from alkali metals including ammonium, lithium, sodium, potassium, and cesium; alkaline earth metals including calcium, magnesium, and aluminum; zinc, barium, choline, and quaternary ammonium compounds.

[0271] In some embodiments, examples of organic salts of carboxylic acids or hydroxyls may be selected from arginine, organic amines, aliphatic organic amines, alicyclic organic amines, aromatic organic amines, benzathine, t-butylamine, benetamine (N-benzylphenethylamine), dicyclohexylamine, dimethylamine, diethanolamine, ethanolamine, ethylenediamine, hydravamin, imidazole, lysine, methylamine, meglamine, N-methyl-D-glucamine, N,N'-dibenzylethylenediamine, nicotinamide, organic amines, ornithine, pyridine, picoli, piperazine, procaine, tris(hydroxymethyl)methylamine, triethylamine, triethanolamine, trimethylamine, tromethamine, and urea.

[0272] In various embodiments, the salt may be produced by reacting the free base or free acid form of the product with one or more equivalent amounts of suitable acids or bases in a solvent such as water, by conventional means, for example, by removing the salt in a solvent or medium in which it is insoluble, or under vacuum, or by freeze-drying, or by exchanging the ions of the existing salt for other ions or a suitable ion-exchange resin.

[0273] Pesticide composition

[0274] Another aspect of the present invention relates to a pesticide composition comprising a pesticide-acceptable carrier or diluent and a compound according to an aspect of the present invention. The pesticide composition may contain one or more of the compounds specified above in the present invention. Typically, the pesticide composition of the present invention comprises a compound of the present invention or a pesticide-acceptable salt thereof and a pesticide-acceptable carrier or diluent. The term "pesticide-acceptable carrier" refers to any suitable adjuvant, carrier, excipient, or stabilizer, which may be in solid or liquid form such as a spray, aerosol, powder, solution, suspension, or emulsion.

[0275] The compounds according to the present invention can be used as herbicides in their unmodified form, but they are generally formulated into compositions in various ways using formulation adjuvants such as carriers, solvents, and surfactants. The formulations can be in various physical forms, such as dusty powders, gels, wettable powders, water-dispersible granules, water-dispersible tablets, effervescent pellets, emulsifying concentrates, microemulsifying concentrates, oil-in-water emulsions, oily fluids, aqueous dispersions, oily dispersions, suspend emulsions, capsule suspensions, emulsifying granules, soluble liquids, water-soluble concentrates (with water or water-miscible organic solvents as carriers), impregnated polymer films, or other known forms. Such formulations can be used as is or diluted before use. Dilution can be carried out, for example, with water, liquid fertilizers, micronutrients, biological organisms, oils, or solvents.

[0276] Typically, the composition contains about 0.01 to 99%, preferably about 20 to 75%, of the active compound together with the adjuvant, carrier, and / or excipient. Individual requirements may vary, and determining the optimal range of effective amounts for each component is within the scope of the art of the art.

[0277] Formulations can be prepared, for example, by mixing the active ingredient with a formulation adjuvant to obtain the composition in the form of a subdivided solid, granules, solution, dispersion, or emulsion. The active ingredient can also be formulated with other adjuvants such as subdivided solids, mineral oil, plant or animal oils, modified plant or animal oils, organic solvents, water, surfactants, or combinations thereof.

[0278] The active ingredient can also be contained in very fine microcapsules. Microcapsules contain the active ingredient in a porous carrier. This allows the active ingredient to be released into the environment in a controlled amount (e.g., sustained release). Microcapsules typically have a diameter of 0.1 to 500 microns. They contain the active ingredient in an amount of about 25 to 95% by weight of the capsule. The active ingredient can be in the form of an integrated solid, fine particles in a solid or liquid dispersion, or in a preferred solution. The encapsulation membrane can include, for example, natural or synthetic rubber, cellulose, styrene / butadiene copolymer, polyacrylonitrile, polyacrylate, polyester, polyamide, polyurea, polyurethane, or chemically modified polymers, and starch xanthetes, or other polymers known to those skilled in the art. Alternatively, the active ingredient can be formed to be contained in subdivided particles in a solid matrix of the base material, but the microcapsules themselves are not encapsulated.

[0279] Suitable formulation adjuvants for preparing the compositions according to the present invention are known themselves. As liquid carriers, water, toluene, xylene, petroleum ether, vegetable oil, acetone, methyl ethyl ketone, cyclohexanone, acid anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, butylene carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetate, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, dimethylformamide (DMF), dimethyl sulfoxide (DMSO), 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkylpyrrolidone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1-Trichloroethane, 2-Heptanone, Alpha-Pinene, d-Limonene, Ethyl Lactate, Ethylene Glycol, Ethylene Glycol Butyl Ether, Ethylene Glycol Methyl Ether, Gamma-Butyrolactone, Glycerol, Glycerol Acetate, Glycerol Diacetate, Glycerol Triacetate, Hexadecane, Hexylene Glycol, Isoamyl Acetate, Isobornyl Acetate, Isooctane, Isophorone, Isopropylbenzene, Isopropyl Myristate, Lactic Acid, Laurylamine, Mesityl Oxide, Methoxypropanol, Methyl Isoamyl Ketone, Methyl Isobutyl Ketone, Methyl Laurate, Methyl Octanoate, Methyl Oleate, Methylene Chloride, m-Xylene, n-Hexane, n-Octylamine, Octadecanoic Acid, Octylamine Acetate, Olein Acids, oleylamine, o-xylene, phenol, polyethylene glycol, propionic acid, propyl lactate, propylene carbonate, propylene glycol, propylene glycol methyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylene sulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol methyl ether, diethylene glycol methyl ether, methanol, ethanol, isopropanol, and high molecular weight alcohols such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, ethylene glycol, propylene glycol, glycerol, and methyl-2-pyrrolidone may be used.

[0280] Suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgaite clay, diatomaceous earth, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed husks, wheat flour, soybean flour, pumice, wood flour, ground walnut shells, lignin, and similar materials.

[0281] Numerous surface-active substances can be advantageously used in both solid and liquid formulations, particularly in formulations that can be diluted with a carrier before use. Surface-active substances may be anionic, cationic, nonionic, or polymeric, and they can be used as emulsifiers, wetting agents, or suspending agents, or for other purposes. Typical surfactants include, for example, salts of alkyl sulfates such as diethanolammonium lauryl sulfate, salts of alkylaryl sulfonic acids such as calcium dodecylbenzenesulfonate, alkylphenol / alkylene oxide addition products such as nonylphenol ethoxylate, alcohol / alkylene oxide addition products such as tridecyl alcohol ethoxylate, soaps such as sodium stearate, salts of alkylnaphthalene sulfonic acids such as sodium dibutylnaphthalenesulfonate, dialkyl esters of sulfosuccinate salts such as sodium di(2-ethylhexyl) sulfosuccinate, sorbitol esters such as sorbitol oleate, quaternary amines such as lauryltrimethylammonium chloride, polyethylene glycol esters of fatty acids such as polyethylene glycol stearate, block copolymers of ethylene oxide and propylene oxide, and salts of mono- and di-alkyl phosphate esters, as well as further substances known in the art.

[0282] Further adjuvants that can be used in herbicidal formulations include crystallization inhibitors, viscosity modifiers, suspension agents, pigments, antioxidants, foaming agents, light absorbers, mixing aids, defoamers, complexing agents, neutralizing or pH adjusting substances and buffers, corrosion inhibitors, fragrances, wetting agents, uptake enhancers, micronutrients, plasticizers, flowing agents, lubricants, dispersants, thickeners, antifreezes, fungicides, and liquid and solid fertilizers.

[0283] The compositions according to the present invention may include additives comprising plant or animal-derived oils, mineral oils, alkyl esters of such oils, or mixtures of such oils and oil derivatives. The amount of oil additives in the compositions according to the present invention is generally 0.01 to 10%, depending on the mixture applied. For example, after the spray mixture is prepared, the oil additives can be added to the spray tank at the desired concentration. Preferred oil additives include mineral oils or plant-derived oils, such as rapeseed oil, olive oil, or sunflower oil, emulsified vegetable oils, alkyl esters of vegetable-derived oils, such as methyl derivatives, or animal-derived oils such as fish oil or beef tallow. Preferred oil additives include C8-C 22 Alkyl esters of fatty acids, especially C 12 -C 18 This includes methyl derivatives of fatty acids, such as methyl esters of lauric acid, palmitic acid, and oleic acid (methyl laurate, methyl palmitate, and methyl oleate, respectively). Other oil derivatives include, for example, Compendium of Herbicide Adjuvants, 10 th This is known to those skilled in the art from Edition, Southern Illinois University, 2010.

[0284] The herbicide composition generally comprises 0.1 to 99% by weight, particularly 0.1 to 95% by weight, of the compound according to the present invention, and 1 to 99.9% by weight of a formulation adjuvant, preferably containing 0% to 25% by weight of a surfactant. The composition of the present invention generally comprises 0.1 to 99% by weight, particularly 0.1 to 95% by weight, of the compound according to the present invention, and 1 to 99.9% by weight of a formulation adjuvant, preferably containing 0% to 25% by weight of a surfactant. Commercial products may be formulated preferably as concentrates, but end users typically use diluted formulations.

[0285] The application rate varies within a wide range and depends on soil properties, application method, crop plants, pests being controlled, prevailing climatic conditions, and other factors influenced by the application method, timing, and target crop. As a general guideline, the compound may be applied at rates of 1 to 2000 l / ha, particularly 10 to 1000 l / ha. Preferred formulations may have the following compositions (by weight):

[0286] Emulsifiable concentrate: ● Active ingredients: 1-95%, preferably 60-90% ●Surfactants: 1-30%, preferably 5-20% ●Liquid carrier: 1-80%, preferably 1-35%

[0287] dust: ●Active ingredient: 0.1-10%, preferably 0.1-5% ●Solid carrier: 90-99.9%, preferably 99-99.9%

[0288] Suspension concentrate: ● Active ingredients: 5-75%, preferably 10-50% ●Water: 24-94%, preferably 30-88% ●Surfactants: 1-40%, preferably 2-30%

[0289] Moisturizing powder: ● Active ingredient: 0.5-90%, preferably 1-80% ● Surfactant 0.5-20%, preferably 1-15% ●Solid carrier: 5-95%, preferably 15-90%

[0290] Granules: ●Active ingredient: 0.1-30%, preferably 0.1-15% ●Solid carrier: 70-99.5%, preferably 85-97%

[0291] When the compounds or pesticide compositions of the present invention are applied to control undesirable plant growth, the pesticide compositions may also include, or be applied in combination with, other pesticides or treatment regimens currently known or to be developed for controlling the growth of various types of plants.

[0292] Therefore, the compositions of the present invention may further include, but are not limited to, herbicides, at least one additional pesticide. For example, the compounds according to the present invention may also be used in combination with other herbicides or plant growth regulators. In preferred embodiments, the additional pesticide is an herbicide and / or herbicide antidote.

[0293] Examples of herbicides that can be used in combination with the compounds of the present invention include acetochlor, acyfluorphen (including acyfluorphen-sodium), acroniphen, arachlor, alloxidim, ametrin, amicarbazone, amidosulfuron, aminocyclopyrachlor, aminopyralide, amitorol, aslam, atrazine, bensulfuron (including bensulfuron-methyl), bentazon, bicyclopyrone, viranaphos, bifenox, bispiribac-sodium, bixlozone, bromacil, bromoxynil, butachlor, and butaf Enacyl, cafenstrol, carfentrazone (containing carfentrazone-ethyl), chloranslam (containing chloranslam-methyl), chlorimuron (containing chlorimuron-ethyl), chlorotoluron, cinosulfuron, chlorsulfuron, scinmethylline, clasiphos, cretodym, clodinahop (containing clodinahop-propargyl), chromazon, clopyralide, cyclopyranil, cyclopyrimorate, cyclosulfamuron, cyhalofop (containing cyhalofop-butyl), 2,4-D (choline salt and its 2-ethylhexyl (Containing esters), 2,4-DB, dimuron, desmedifam, dicamba (containing aluminum, aminopropyl, bisaminopropylmethyl, choline, dichloroprop, diglycolamine, dimethylamine, dimethylammonium, and their potassium and sodium salts), diclohop-methyl, diclolam, diflufenican, diphenzoquat, diflufenican, diflufenzopyr, dimethachlor, dimethenamide-P, diquatdibromide, diuron, esprocarb, ethalfluralin, etofmesate, phenoxaprop ( (containing phenoxaprop-P-ethyl), phenoxasulfone, fenquinotrione, fentrazamide, flazasulfuron, florathlam, florpiraxifen, fluazihop (containing fluazihop-P-butyl), flucarbazone (containing flucarbazone-sodium), fluphenacet, flumetraline, flumetulam, flumioxazine, flupirsulfuron (containing flupirsulfuron-methyl-sodium), fluroxypil (containing fluroxypil-meptyl), fluthiaceto-methyl, fomesafen, forumsulfuron,Glufosinate (including its ammonium salt), glyphosate (including diammonium salt, isopropylammonium, and its potassium salt), haloxifen (including haloxifen-methyl), halosulfuron-methyl, haloxyhop (including haloxyhop-methyl), hexazinone, hydantosidine, imazamox, imazapix, imazapyr, imazakine, imazetapir, indadiflame, iodosulfuron (including iodosulfuron-methyl-sodium), iophenesulfuron, iophenesulfuron-sodium, ioxinyl, Ifencarbazone, isoproturone, isoxaben, isoxaflutol, lactofen, lancotrione, linuron, MCPA, MCPB, mecoprop-P, mefenacet, mesosulfuron, mesosulfuron-methyl, mesotrione, metamitron, metazachlor, methiozoline, metobromurone, metrachlor, metoslam, metoxlon, metovudine, metosulfuron, molinate, napropamide, nicosulfuron, norflurazone, orthosulfamurone, oxaziargyl, oxadiazone, oxasulfuron, oxyfluorphen Paraquat dichloride, bendimethalin, penoxulam, fenmedifam, picloram, picolinafene, pinoxadene, pretilachlor, primisulfuron-methyl, prodiamine, promethrin, propachlor, propanyl, propaxafop, profam, propyrisulfuron, propizamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen (including pyraflufen-ethyl), pyrasulfol, pyrazolinate, pyrazosulfuron-ethyl, pyribenzoxime, pyridate, pyrifthalide, pyrimisulfan, pyrithiobacter C-Sodium, Pyroxasulfone, Pyroxulam, Quinclorac, Kimmelac, Quizalofop (including Quizalofop-P-ethyl and Quizalofop-P-tefuryl), Limusulfuron, Saflufenacil, Cethoxydim, Simazine, S-Methrachlor, Sulcotrione, Sulfenthrazone, Sulfosulfuron, Tebuthiuron, Tefuryltrione, Tempotrione, Terbutyrazine, Terbutrin, Thiencarbazone, Thiensulfuron, Thiafenacil, Tolpyrate, Topramezone, Tralcoxidim, Triafamone, Triallate,Triasulfuron, Trivenuron, (containing Triaberonuron-methyl), Triclopyr, Trifloxysulfuron (containing Trifloxysulfuron-sodium), Trifludimoxazine, Triflulari, Triflusulfuron, Tritosulfuron, 4-Hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidine-2-one, 4-Hydroxy-1,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidine-2-one, 5-Ethoxy-4-hydroxy-1- Methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidine-2-one, 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidine-2-one, 4-hydroxy-1,5-dimethyl-3-[1-methyl-5-(trifluoromethyl)pyrazole-3-yl]imidazolidine-2-one, (4R)1-(5-tert-butylisoxazole-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidine-2-one, 3-[2-(3,4-dimethoxyphenyl)-6 -methyl-3-oxopyridazin-4-carbonyl]bicyclo[3.2.1]octane-2,4-dione, 2-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxopyridazin-4-carbonyl]-5-methylcyclohexane-1,3-dione, 2-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxopyridazin-4-carbonyl]cyclohexane-1,3-dione, 2-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxopyridazin-4-carbonyl]-5,5-dimethylcyclohexane Xan-1,3-dione, 6-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxopyridazine-4-carbonyl]-2,2,4,4-tetramethylcycloexane-1,3,5-trione, 2-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxopyridazine-4-carbonyl]-5-ethylcyclohexane-1,3-dione, 2-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxopyridazine-4-carbonyl]-4,4,6,6-tetramethylcyclohexane-1,3-dione,2-[6-cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxopyridazin-4-carbonyl]-5-methylcyclohexane-1,3-dione, 3-[6-cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxopyridazin-4-carbonyl]bicyclo[3.2.1]octane-2,4-dione, 2-[6-cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxopyridazin-4-carbonyl]-5,5-dimethylcyclohexane-1,3-dione, 6-[6-cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxopyridazin-4-carbonyl]-2,2,4 These include, but are not limited to, 4-tetramethyl-cyclohexane-1,3,5-trione, 2-[6-cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxopyridazine-4-carbonyl]cyclohexane-1,3-dione, 4-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxopyridazine-4-carbonyl]-2,2,6,6-tetramethyl-tetrahydropyran-3,5-dione, and I+4-[6-cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxopyridazine-4-carbonyl]-2,2,6,6-tetramethyl-tetrahydropyran-3,5-dione. These additional agents may also exist in the form of their esters or salts.

[0294] The compounds of the present invention can also be combined with herbicide antidotes. Examples of herbicide antidotes include, but are not limited to, benoxacol, croquintocet (including croquintocet-mexyl), cyprosulfamide, dichlormid, fenchlorazole (including fenchlorazole-ethyl), fenchlorim, fluxofenim, flirazole, isoxadifen (including isoxadifen-ethyl), mefenpyr (including mefenpyr-diethyl), metcamifen, N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide, and oxavethrinil, all of which may be in the form of their esters or salts.

[0295] The compounds of the present invention can also be used in mixtures with other pesticides such as fungicides, nematicides, or insecticides, examples of which are known to those skilled in the art.

[0296] The mixing ratio of the compound of the present invention to the additional agent is preferably 1:100 to 1000:1. Preferably, the mixing ratio of the compound of the present invention to the antidote is 100:1 to 1:10, and particularly 20:1 to 1:1.

[0297] The mixture can be advantageously used in the above formulations (in such cases, “active ingredient” refers to the respective mixtures of the compound of the present invention and the additional agent).

[0298] Herbicide activity

[0299] In various embodiments, the present invention provides compounds and compositions, including any embodiment described herein, for use in any of the methods of the present invention. In various embodiments, the use of the compounds of the present invention or compositions containing them has the effect of inhibiting, suppressing, enhancing, or stimulating a desired response, as will be understood by those skilled in the art. In some embodiments, the compositions may further comprise additional active ingredients whose activity is useful for the particular application to which the compounds of the present invention are applied.

[0300] The compounds of the present invention are useful as herbicides or herbicidal compounds. Accordingly, the present invention further includes a method for controlling undesirable plant growth, the method comprising applying an effective amount of the compounds of the present invention, or a pesticide composition thereof, to plants or locations containing them, under conditions that are effective in controlling undesirable plant growth, particularly weed growth, in crops of useful plants.

[0301] In some embodiments, "controlling" according to the present invention refers to stopping, reducing, or slowing growth, or preventing or reducing germination. Generally, the plants being controlled are unwanted plants (weeds).

[0302] In some embodiments, “location” refers to an area where plants are growing or will grow.

[0303] The application rate of the compounds of the present invention varies within a wide range of limits and may depend on soil properties, application method (e.g., pre-planting, pre-emergence, post-emergence, application to seed furrows, no-till application, etc.), crop plants, controlled weeds, influential climatic conditions, and other factors that depend on the application method, timing, and target crop. The compounds of the present invention are generally applied at rates of 10 to 2000 g / ha, particularly 50 to 1000 g / ha.

[0304] In some embodiments, application is carried out by spraying the composition, typically by a tractor equipped with a sprayer for large areas, but other methods such as dusting, dripping, or drenching (in powder) can also be used.

[0305] In some embodiments, useful plants on which the compositions according to the present invention can be used include, but are not limited to, crops such as barley and wheat, wheat, rapeseed, sunflower, maize, rice, soybeans, sugar beets, sugarcane, and turfgrass.

[0306] In some embodiments, crop plants also include trees such as fruit trees, palm trees, coconut trees, or other nut trees. They also include climbing plants such as grapes, fruit shrubs, fruit plants, and vegetables.

[0307] In some embodiments, the crops are resistant crops. Therefore, in some embodiments, the crops also include crops that have been made resistant to herbicides or classes of herbicides (including, but not limited to, ALS-, GS-, EPSPS-, PPO-, ACCase-, and HPPD- inhibitors) by conventional propagation methods or by genetic engineering. Examples of crops made resistant to herbicides by genetic engineering include, but are not limited to, glyphosate and glufosinate-resistant maize varieties marketed under trade names RoundupReady® and LibertyLink®. In other embodiments, the crops also include those made resistant to pests by genetic engineering. Examples of such crops include, but are not limited to, Bt maize (resistant to the European pine borer), Bt cotton (resistant to the Mexican cotton weevil), and Bt potato (resistant to the Colorado potato beetle). A non-limiting example of Bt maize is the Bt176 maize hybrid from NK® (Syngenta Seeds). Non-limiting examples of transgenic plants containing one or more genes encoding insecticide resistance and expressing one or more toxins include KnockOut® (maize), Yield Gard® (maize), NuCOTIN33B® (men), Bollgard® (men), NewLeaf® (potato), NatureGard®, and Protexcta®. Plant crops or their seed materials can be both herbicide-resistant and insect-feeding-resistant ("overlapping" transgenic events).

[0308] In some embodiments, crops are obtained by conventional methods of propagation or genetic engineering and include so-called output traits (e.g., improved storage stability, higher nutritional value, and improved flavor). Other useful plants include, for example, turfgrass for golf courses, lawns, parks, and roadsides, or turfgrass grown commercially for turf soil, as well as ornamental plants such as flowers or shrubs.

[0309] Herbicides, or chemically active herbicides, can be classified into pre-planting herbicides, pre-emergence herbicides, and post-emergence herbicides. Pre-planting and pre-emergence herbicides typically prevent weed seed germination and are applied before and after planting or sowing, respectively, but before seed germination, while post-emergence herbicides kill weeds after the seeds have germinated and weed growth has begun.

[0310] When applying the compounds of the present invention, they can be applied before planting, before sprouting, after sprouting, or both.

[0311] In various embodiments, the present invention relates to a method for controlling the growth of undesirable plants, comprising applying a compound or a pesticide composition thereof according to the present invention to farmland. In some embodiments, the compound is a pre-planting herbicide. In some embodiments, the compound is a pre-emergence herbicide. In some embodiments, the compound is a post-emergence herbicide. Therefore, in some embodiments, the compound is applied to farmland before the undesirable plants sprout (i.e., a pre-emergence or pre-planting herbicide). In some embodiments, the compound is applied to farmland after the undesirable plants have germinated (i.e., a post-emergence herbicide).

[0312] In various embodiments, the compounds and pesticide compositions according to the present invention are used to control undesirable plants, including a wide variety of monocotyledonous and dicotyledonous weed species.

[0313] In some embodiments, the undesirable plant is a weed. In some embodiments, the undesirable plant is a true dicotyledonous plant (dicotyledonous or dicotyledonous). In some embodiments, the undesirable plant is a monocotyledonous plant (monocotyledonous or monocotyledonous).

[0314] Non-limiting examples of monocotyledonous plant species that can be typically controlled include Alopecurus myosuroides, Avena fatua, Brachiaria plantaginea, Bromus tectorum, Cyperus esculentus, Digitaria sanguinalis, Echinochloa crus-galli, Lolium perenne, Lolium multiflorum, Panicum miliaceum, Poa annua, Setaria viridis, Setaria faberi, and Sorghum bicolor, each representing a distinct embodiment of the present invention.

[0315] Non-limiting examples of controllable dicotyledonous plant species include Abutilon theophrasti, Amaranthus retroflexus, Bidens pilosa, Chenopodium album, Euphorbia heterophylla, Gallium aparine, Ipomoea hederacea, Kochia scoparia, Polygonum convolvulus, Sida spinosa, Sinapis arvensis, Solanum nigrum, Stellaria media, Veronica persica, and Xanthium strumarium, each representing a distinct embodiment of the present invention.

[0316] In some embodiments, undesirable plants are Abutilon theophrasti, Amaranthus palmeri, Ambrosia artemisiifolia, Alopecurus myosuroides, Avena sterilis, Chenopodium album, Conyza Canadensis, Digitalia sanguinalis, Echinochloa colona, ​​Euphorbia heterophylla, Lolium perenne, Lolium rigidum, Matricaria chamomilla, Phalaris paradoxa, Poa annua, Portulaca oleracea, Setaria viridis, Solanum nigrum, or any combination thereof. In some embodiments, the compound is one of the compounds listed in Tables 1 and 2, each compound representing a distinct embodiment according to the present invention.

[0317] In some embodiments, the compounds and compositions according to the present invention are used to control undesirable vegetation in rice. In certain embodiments, undesirable vegetation includes Brachiaria platyphylla (Groseb.) Nash (large-leaved signal grass, BRAPP), Digitaria sanguinalis (L.) Scop (large dwarf grass, DIGSA), Echinochloa crus-galli (L.) P. Beauv. (dog shrimp, ECHCG), Echinochloa colonum (L.) LINK (Waseda barnyard grass, ECHCO), Echinochloa oryzoides (Ard.) Fritsch (early barnyard grass, ECHOR), Echinochloa oryzicola (Vasinger) Vasinger (late barnyard grass, ECHPH), Ischaemum rugosum Salisb. (Salamora grass, ISCRU), Leptochloa chinensis (L.) Nees (also known as moss grass, LEFCH), and Leptochloa fascicularis (Lam.) Gray (LEFFA), Leptochloa panicoides (Presl.) Hitchc. (Amazon Azegaya, LEFPA), Panicum dichotomiflorum (L.) Michx. (PANDI), Paspalum dilatatum Poir. (PASDI), Cyperus difformis Cyperus esculentus L. (CYPES), Cyperus iria L. (CYPIR), Cyperus rotundus L. (CYPRO), Eleocharis species (ELOSS), Fimbristylis miliacea (L.) Vahl (Hyderico, FIMMI), Schoenoplectus juncoides Roxb. (Scirpus juncoides, SCPJU), Schoenoplectus maritimus L. (Scirpus juncoides, SCPMA), Schoenoplectus mucronatus L.(Inada bulrush, SCPMU), Aeschynomene species, (grass bulrush, AESSS), Alternanthera philoxeroides (Mart.) Griseb. (long-stemmed amaranth, ALRPH), Alisma plantago-aquatica L. (spoon-leaved arrowhead, ALSPA), Amaranthus species (pygweed and amaranth, AMASS), Ammannia coccinea Rottb. (narrow-leaved loosestrife, AMMCO), Eclipta alba (L.) Hassk. (American eclipta, ECLAL), Heteranthera limosa (SW.) Willd. / Vahl (American eclipta, HETLI), Heteranthera reniformis R.&P. (dwarf water hyacinth, HETRE), Ipomoea hederacea (L.) Jacq. (American morning glory, IPOHE), Lindernia dubia (L) Pennell (American dwarf These are *Indica (Willd.) Koehne* (Rotin), *Sagittaria* species (Sagittaria, SAGSS), *Sesbania exaltata (Raf) Cory / Rydb. Ex Hill* (Hemp Sesbania, SEBEX), or *Sphenoclea zeylanica Gaertn.* (Gooseweed, SPDZE), each representing a distinct embodiment of the present invention. In some embodiments, the compound is one of the compounds listed in Tables 1 and 2, each representing a distinct embodiment of the present invention.

[0318] In some embodiments, the compounds and compositions according to the present invention are used to control undesirable vegetation in cereals. In certain embodiments, the undesirable vegetation includes Alopecurus myosuroides Huds. (Alomey), Apera spica-venti (L.) Beauv. (Windgrass, APESV), Avena fatua L. (Browngrass, AVEFA), Bromus tectorum L. (Horse browngrass, BROTE), Lolium multiflorum Lam. (Ricegrass, LOLMU), Phalaris minor Retz. (Dwarf canary grass, PHAMI), Poa annua L. (Annual bluegrass, POAAN), Setaria pumila (Poir.) Roemer & J.A. Schultes (Golden foxtail, SETLU), Setaria viridis (L.) Beauv. (Foxtail grass, SETVI), and Cirsium. arvense(L.) Scop. (CIRARy), Gallium aparine L. (GALAP), Kochia scoparia (L.) Schrad. (KCHSC), Lamium purpureum L. (LAMPU), Matricaria recutita L. (MATCH), Matricaria matricarioides(Less.)Porter(MATMT), Papaver rhoeas L.(Papary, PAPRH), Polygonum convolvulus L.(POLCO), Salsola tragus L.(Russian thistle, SASKR), Stellaria media(L.)VilL(Chickweed, STEME), Veronica persica Poir. (VERPE), Viola arvensis Murr. (field violet, VIOAR) or Viola tricolor L. (wild violet, VIOTR), each representing a distinct embodiment of the present invention.In some embodiments, the compound is one of the compounds listed in Tables 1 and 2, and each compound represents a separate embodiment of the present invention.

[0319] In some embodiments, the compounds and compositions according to the present invention are used to control undesirable vegetation in pastures and grasslands. In certain embodiments, undesirable vegetation includes Ambrosia artemisiifolia L. (ragweed, AMBEL), Cassia obtusifolia (senna, CASOB), Centaurea maculosa auct. non Lam. (variegated cornflower, CENMA), Cirsium arvense (L.) Scop. (Canadian thistle, CIRAR), Convolvulus arvensis L. (morning glory, CONAR), Euphorbia esula L. (European daisy, EPHES), Lactuca serriola L. / Tom. (spiny lettuce, LACSE), Plantago lanceolata L. (broadleaf plantain, PLALA), Rumex obtusifolius L. (Japanese dock, RUMOB), Sida spinosa L. (prikrysanthemum, SIDSP), and Sinapis arvensis L. (wild mustard, SINAR), Sonchus arvensis L. (Taiwanese mustard, SONAR), Solidago species (Solidago, SOOSS), Taraxacum officinale GHWeber ex Wiggers (common dandelion, TAROF), Trifolium repens L. (white clover, TRFRE), or Urtica dioica L. (nettle, URTDI), each representing a distinct embodiment of the present invention. In some embodiments, the compound is one of the compounds listed in Tables 1 and 2, each representing a distinct embodiment of the present invention.

[0320] In some embodiments, the compounds and compositions according to the present invention are used to control undesirable vegetation observed in row crops. In certain embodiments, undesirable vegetation includes Alopecurus myosuroides Huds. (Alomey), Avena fatua L. (Avefa), Brachiaria platyphylla (Groseb.) Nash (Brapp), Digitaria sanguinalis (L.) Scop (DIGSA), Echinochloa crus-galli (L.) P.Beauv. (ECHCG), Echinochloa colonum (L.) Link (ECHCO), Lolium multiflorum Lam. (LOLMU), Panicum dichotomiflorum Michx. (PANDI), Panicum miliaceum L. (PANMI), and Setaria faberi. Herrm. (SETFA), Setaria viridis (L.) Beauv. (SETVI), Sorghum halepense (L.) Pers. (SORHA), Sorghum bicolor (L.) Moench ssp. Arundinaceum (SORVU), Cyperus esculentus Cyperus rotundus L. (CYPRO), Abutilon theophrasti Medik. (ABUTH), Amaranthus species (pigweed and amaranth, AMASS), Ambrosia artemisiifolia L. (AMBEL), Ambrosia psilostachya DC. (Western Ragweed, AMBPS), Ambrosia trifida L. (AMBTR), Asclepias syriaca L. (ASCSY), Chenopodium album L. (CHEAL), Cirsium arvense (L.) Scop.(Canadian thistle, CIRAR), Commelina benghalensis L. (Combe), Datura stramonium L. (White-flowered Korean stramonium, DATST), Daucus carota L. (Carrot, DAUCA), Euphorbia heterophylla L. (Wild poinsettia, EPHHL), Erigeron bonariensis L. (Wild daisy, ERIBO), Erigeron canadensis L. (Dwarf confectionery, ERICA), Helianthus annuus L. (Sunflower, HELAN), Jacquemontia tamnifolia (L.) Griseb. (Small-flowered morning glory, IAQTA), Ipomoea hederacea (L.) Jacq. (American morning glory, IPOHE), Ipomoea lacunosa L. (Ipollina), Lactuca serriola L. / Tom. (Lacse), Portulaca oleracea L. (Porol), Sida spinosa L. (SIDSP), Sinapis arvensis L. (SINAR), Solanum ptychanthum Dunal (SOLPT), or Xanthium strumarium L. (XANST), each representing a distinct embodiment of the present invention. In some embodiments, the compound is one of the compounds listed in Tables 1 and 2, each representing a distinct embodiment of the present invention.

[0321] The following embodiments are provided to more fully illustrate preferred embodiments of the present invention. However, they should not be construed as limiting the broad scope of the present invention. [Examples]

[0322] Example 1

[0323] Synthetic details of the compound of the present invention

[0324] [ka]

[0325] Scheme 1. Synthetic routes and procedures for compounds 104, 105, 106, 114, and 115.

[0326] Compounds 106, 115, and 114 were prepared using the same route with preferred enantiomers of threonine.

[0327] Step M:

[0328] To a solution of compound 1 (40 g, 336 mmol) in methanol (400 mL), SOCl2 (39.4 mL, 543 mmol) was added dropwise at 0°C. The reaction mixture was refluxed and concentrated under reduced pressure to obtain the crude product, which was used in the next step without further purification.

[0329] Step N:

[0330] To the solution from the previous step, MeCN (300 mL) and methanol (250 mL) were added. Then, at 0°C, Boc₂O (92.2 mL, 401 mmol) and triethylamine (105 mL, 753 mmol) were added dropwise, and the mixture was stirred overnight. Subsequently, it was concentrated under reduced pressure, dissolved in dichloromethane (400 mL) and water (400 mL), and extracted with dichloromethane (2 × 200 mL). The mixed organic layer was washed with 2N HCl (200 mL) and K₂SO₄, dried over Na₂SO₄, and concentrated to obtain 74.6 g of compound 3 (320 mmol, 95% yield in 2 steps).

[0331] Step O:

[0332] Compound 3 (74.6 g, 320 mmol) was dissolved in MeCN (1200 mL) and dimethoxypropane (358 mL), cooled to 10-15°C, and then BF3·Et2O (2.39 mL, 19.4 mmol) was added. The solution was stirred overnight. Then, triethylamine (16 mL, 115 mmol) was added, the solution was concentrated under reduced pressure, dissolved in water (300 mL), extracted with dichloromethane (3 × 300 mL), dried over Na2SO4, and concentrated to obtain crude product 4, which was used in the next step without further purification.

[0333] Step P:

[0334] Crude product 4, dissolved in THF (200 mL), was added dropwise by adding a solution of LiAlH4 (13 g, 343 mmol) in THF (700 mL), and the mixture was stirred overnight. The mixture was then quenched with a solution of KOH (6.7 g, 119 mmol) in water (90 mL), filtered, and the resulting precipitate was washed with THF. The filtrate was concentrated under reduced pressure. The crude residue was purified by column chromatography to obtain 39 g of compound 5 (159 mmol, 50% yield in 2 steps).

[0335] Step Q:

[0336] To a solution of compound 5 (24.05 g, 98.0 mmol) in dichloromethane (420 mL), dess-martin periodinane (50.4 g, 119 mmol) was gradually added, and the reaction mixture was stirred overnight. Solutions of NaHCO3 (42.2 g, 502 mmol) and Na2SO4 (189.2 g, 1332 mmol) in water (700 mL) were added, and the mixture was stirred until the entire precipitate was dissolved. The reaction mixture was separated, the aqueous layer was extracted with dichloromethane (2 × 200 mL), the organic layer was dried over Na2SO4, and concentrated to obtain 20.3 g of compound 6 (83.4 mmol, yield 85%).

[0337] Step R:

[0338] Ethyl 4-bromocrotonate (7) (20.00 g, 93.24 mmol) was added all at once to triethylphosphine (17.71 g, 106.56 mmol) at 120-130°C, and the solution was stirred for 1 hour. By distillation of the resulting reaction mixture, 20.39 g of compound 8 was provided as a pale yellow oil (81.5 mmol, yield 88%).

[0339] Step S:

[0340] K2CO3 (57.7 g, 418 mmol) and 18-crown-6 (36.9 g, 140 mmol) were dissolved in toluene and stirred for 1 hour. The solution was cooled to -20°C, and then compound 8 (20.39 g, 81.5 mmol) and compound 6 (16.9 g, 69.5 mmol) were added dropwise. The reaction mixture was then heated to rt, stirred, and monitored by TLC (for 1-2 days). After the reaction was complete, water (300 mL) was added, the solution was extracted with hexane (2 × 200 mL), the mixed organic layer was washed with water (2 × 150 mL) and 5% citric acid (100 mL), dried over Na2SO4, and concentrated under reduced pressure. The crude residue was purified by column chromatography to obtain 17 g of compound 9 (50.1 mmol, 72% yield).

[0341] Step T:

[0342] To a solution of compound 9 (16.5 g, 48.6 mmol) in ethanol (200 mL), 10% Pd / C (1 g) was added. The reaction flask was evacuated, and the solution was stirred overnight under an H2 atmosphere. The solution was then filtered and concentrated under reduced pressure to obtain 16 g of compound 10 (46.6 mmol, 96% yield).

[0343] Step U:

[0344] Compound 10 was dissolved in methanol (150 mL), and p-toluenesulfonic acid (0.1 g, 0.581 mmol) was added. The reaction mixture was stirred overnight and then concentrated under reduced pressure. Next, a solution of K2CO3 (1 g, 7.24 mmol) in water (30 mL) was added, and the mixture was extracted with MTBE (3 × 100 mL), dried over Na2SO4, and concentrated to obtain a mixture of 14.1 g of ester 11 (esterification was carried out under a Me:Et = 2:1 ratio in this reaction), which was used in the next step.

[0345] Step V1:

[0346] A mixture of ester 11 (2.69 g) was dissolved in a solution of THF (80 mL), methanol (25 mL), and water (25 mL), and then LiOH·H2O (1.1 g, 26.2 mmol) was added at 0°C. The solution was heated to rt and stirred. Then, the THF and methanol were evaporated under reduced pressure, the resulting aqueous solution was cooled, acidified with a 1.2 N solution of NaHSO4, extracted with MTBE (3 × 50 mL), dried on Na2SO4, concentrated under vacuum, and purified by reverse-phase chromatography. Partial racemization (85:15) occurred at the Horner step, but the diastereomer was separated at the reverse-phase chromatography step, yielding 0.6 g of compound 14 (2.18 mmol, yield 25%).

[0347] Step V2:

[0348] Compound 14 (0.6 g, 2.18 mmol) was dissolved in MTBE (4 mL), Di / HCl (2.5 mL) was added, and the resulting mixture was stirred overnight. The precipitate was filtered, washed with MTBE, and dried under reduced pressure to obtain 0.36 g of the hydrochloride salt of target compound 104 (2.05 mmol, 94%). m / z = 176.2 1H NMR(400MHz,dmso)δ(ppm):12.04(bs,1H,COOH), 7.89(bs,3H,NH3), 5.25(s,1H,OH), 3.85(m,1H,CH), 2.9 7(m,1H,CH), 2.19(t,J=7.12Hz,2H,CH2-COOH), 1.48-1.30(m,6H,CH2-CH2-CH2), 1.06(d,J=6.36Hz,CH3).

[0349] Step W:

[0350] A solution of compound 11 (7.05 g, 28.7 mmol) in THF (30 mL) was added dropwise to a solution of NaH (1.4 g, 35.0 mmol) in THF (300 mL) at 0°C. The solution was heated to rt and stirred overnight. Then, it was poured into a mixture of ice water (200 mL) and NH4Cl (6 g, 112 mmol), the layers were separated, the aqueous layer was extracted with MTBE (3 × 100 mL), dried over Na2SO4, and concentrated to obtain 4.5 g of crude product, compound 12, which was used in the next step without further purification.

[0351] Step X:

[0352] A mixture of ester 12 (1.5 g) was dissolved in a solution of THF (40 mL), methanol (15 mL), and water (15 mL), and then LiOH·H2O (0.96 g, 22.9 mmol) was added at 0°C. The solution was heated to rt and stirred. After evaporating the THF and methanol under reduced pressure, the resulting aqueous solution was cooled, acidified with a 1.2 N solution of NaHSO4, extracted with MTBE (3 × 50 mL), dried over Na2SO4, and concentrated under vacuum to obtain 0.87 g of crude product, compound 105 (62%). Partial racemization was performed at the Horner step (85:15).

[0353] Step Y:

[0354] To a solution of diastereomer acid (0.87 g, 4.96 mmol) from the previous step in DMF (10 mL), K2CO3 (1.19 g) and benzyl bromide (0.56 mL, 4.71 mmol) were added, and the reaction mixture was stirred overnight. Then, water (40 mL) was added thereto, and the mixture was extracted with MTBE (3 × 50 mL). The organic layer was washed with water (5 × 30 mL), dried over Na2SO4, concentrated under reduced pressure, and purified by reverse-phase chromatography to obtain 0.6 g (48%) of the crude product, which was then purified by chiral column chromatography to obtain 0.36 g of the required diastereomer 13 (0.012 mmol, 60%).

[0355] Step Z:

[0356] To a solution of compound 13 (0.36 g, 1.31 mmol) in methanol (5 mL), 10% Pd(C) (0.1 g) was added. The flask was degassed, and the reaction was carried out under an H2 atmosphere with stirring overnight. The solution was then filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography to obtain 0.16 g of target compound 105 (0.795 mmol, 96%).

[0357] From compound (14) in the above scheme, the following can be obtained.

[0358] [ka]

[0359] Scheme 2. The procedure was adapted from Adibi, Hadi; et al., Synthetic Communications (2010), 40(18), 2753-2766.

[0360] Preparation of compounds 123 and 148

[0361] [ka]

[0362] Scheme 3. Synthetic route and procedure for the preparation of compound 123.

[0363] Compound 148 was prepared using the same route, starting with tert-butyl 2-formylpyrrolidine-1-carboxylate (instead of tert-butyl 3-formylpyrrolidine-1-carboxylate), as described below.

[0364] Synthesis of compound 123

[0365] [ka]

[0366] To a solution of compound 1 (754 mg, 3.01 mmol, 1.2 equivalents) in THF (20 mL), NaH (130 mg, 3.26 mmol, 60% purity, 1.3 equivalents) was added at 0-5°C and the mixture was stirred at 25°C for 0.5 hours. Then, compound 123_1 (500 mg, 2.51 mmol, 1 equivalent) was added, and the mixture was stirred at 25°C for 1.5 hours. LC-MS indicated that the reaction was complete. The residue was poured into saturated NH4Cl aqueous solution (50 mL). The aqueous phase was extracted with ethyl acetate (50 mL x 2). The mixed organic phase was washed with brine (50 mL), dried over anhydrous MgSO4, filtered, and concentrated under vacuum. The residue was purified by flash silica gel chromatography (ISCO®, 20g SepaFlash® silica flash column, eluent with a 0-15% ethyl acetate / petroleum ether gradient (100 mL / min)) to obtain compound 123_2 (420 mg, 1.41 mmol, yield 56.0%, purity 98.9%) as a colorless oil.

[0367] 1H NMR:(400MHz,CDCl3)δ 7.19-7.13(m,1H), 6.22-6.05(m,1H), 6.02-5.91(m,1H), 5.89-5.72(m,1H), 4.23-4.03(m,2H), 3.57-3.47(m,1H), 3.42(ddd,J=3.4,8.0,1 0.9Hz,1H), 3.34-3.18(m,1H), 3.08-2.92(m,1H), 2.90-2.75(m,1H), 2.05-1.93(m,1H), 1.75-1.59(m,1H), 1.39(s,9H), 1.26-1.20(m,3H)

[0368] [ka]

[0369] To a solution of compound 123_2 (420 mg, 1.42 mmol, 1 equivalent) in EtOH (20 mL), Pd / C (200 mg, 1.42 mmol, 10% purity, 1 equivalent) was added under N2. The suspension was degassed under vacuum and purged several times with H2. The mixture was stirred under H2 (40 psi) at 25°C for 2 hours. LCMS indicated that the reaction was complete. The reaction mixture was filtered, and the filtrate was concentrated to obtain crude compound 123_3 (327 mg, 1.09 mmol, 76.8% yield) as a colorless oil, which was used in the next step without further purification.

[0370] 1 H NMR:(400MHz,CDCl3)δ 4.12-3.99(m,2H), 3.54-3.27(m,2H), 3.24-3.07(m,1H), 2.85-2.67(m,1H), 2.23(dt,J=3.6,7.2Hz,2H), 2.10-1. 95(m,1H), 1.89(ddt,J=2.9,6.6,9.3Hz,1H), 1.62-1.50(m,3H), 1.39(s,9H), 1.35-1.22(m,4H), 1.22-1.16(m,3H)

[0371] [ka]

[0372] To a solution of compound 123_3 (327 mg, 1.09 mmol) in EtOH (3.00 mL) and H2O (3.00 mL), NaOH (87.4 mg, 2.18 mmol) was added, and the mixture was stirred at 25°C for 2 hours. LC-MS showed that the starting material had been consumed. It was diluted with ethyl acetate (4 mL), the mixture was adjusted to pH 4, the organic layer was dried over MgSO4, filtered, and concentrated. It was used in the next step without further purification. Compound 123_4 (240 mg, 776 μmol, yield 71.0%, purity 87.7%) was obtained as a pale yellow oil.

[0373] 1 H NMR:(400MHz,DMSO-d6)δ 11.99 (br s,1H), 3.45-3.37(m,1H), 3.32-3.27(m,1H), 3.20-3.07(m,1H), 2.79-2.64(m,1H), 2.21 (t,J=7.3Hz,2H), 2.13-1.98(m,1H), 1.91(s,1H), 1.56-1.43(m,2H), 1.39(s,9H), 1.36-1.21(m,4H)

[0374] [ka]

[0375] To a solution of compound 123_4 (240 mg, 884 μmol) in dioxane (2.50 mL), HCl / dioxane (2.50 mL) was added and the mixture was stirred at 25°C for 2 hours. LC-MS showed that the starting material had been consumed. The solvent was removed under reduced pressure to obtain the product. Compound 123 (150 mg, 858 μmol, yield 97.1%, purity 98.0%) was obtained as a pale yellow solid.

[0376] 1H NMR:(400MHz,DMSO-d6)δ 12.05(br d,J=1.9Hz,1H), 9.45(br d,J=1.6Hz,1H), 8.79(br s,1H), 3.25-3.01(m,2H), 2.23 (t,J=7.3Hz,2H), 2.12-2.01(m,1H), 1.98-1.42(m,8H), 1.41-1.26(m,2H)

[0377] Synthesis of compound 148

[0378] [ka]

[0379] To a solution of compound 1 (1.51 g, 6.02 mmol, 1.2 equivalents) in THF (20 mL), NaH was added at 0-5°C (261 mg, 6.52 mmol, 60% purity, 1.3 equivalents), and the mixture was stirred at 25°C for 0.5 hours. Then, compound 148_1 (1.00 g, 5.02 mmol, 1 equivalent) was added, and the mixture was stirred at 25°C for 1.5 hours. LC-MS indicated that the reaction was complete. The residue was poured into saturated NH4Cl aqueous solution (50 mL). The aqueous phase was extracted with ethyl acetate (50 mL x 2). The mixed organic phase was washed with brine (50 mL), dried over anhydrous MgSO4, filtered, and concentrated under vacuum. The residue was purified by flash silica gel chromatography (ISCO®, 20g SepaFlash® silica flash column, eluent with a 0-15% ethyl acetate / petroleum ether gradient (100 mL / min)) to obtain compound 148_2 (640 mg, 2.15 mmol, yield 42.9%, purity 99.3%) as a colorless oil.

[0380] 1 H NMR:(400MHz,CDCl3)δ 7.65-7.12(m,2H), 6.20-5.50(m,3H), 4.81-3.92(m,3H), 3.64-3.06(m,2H), 2. 17-1.90(m,1H), 1.90-1.71(m,2H), 1.71-1.55(m,1H), 1.41-1.27(m,9H), 1.23 (dt,J=1.9,7.1Hz,3H)

[0381] [ka]

[0382] To a solution of compound 148_2 (640 mg, 2.17 mmol, 1 equivalent) in EtOH (20 mL), Pd / C (200 mg, 2.17 mmol, 10% purity, 1 equivalent) was added under N2. The suspension was degassed under vacuum and purged several times with H2. The mixture was stirred under H2 (50 psi) at 25°C for 2 hours. LCMS indicated that the reaction was complete. The reaction mixture was filtered, and the filtrate was concentrated to obtain crude compound 148_3 (540 mg, 1.80 mmol, yield 83.2%) as a colorless oil, which was used in the next step without further purification.

[0383] 1 H NMR:(400MHz,CDCl3)δ 4.05(q,J=7.1Hz,2H), 3.65(q,J=7.0Hz,1H), 3.39-3.14(m,2H), 2.23(t,J=7.5Hz ,2H), 1.90-1.62(m,4H), 1.62-1.48(m,4H), 1.41-1.35(m,9H), 1.28-1.14(m,6H).

[0384] [ka]

[0385] To a solution of compound 148_3 (540 mg, 1.80 mmol) in EtOH (5.00 mL) and H2O (5.00 mL), NaOH (144 mg, 3.61 mmol) was added, and the mixture was stirred at 25°C for 2 hours. LC-MS showed that the starting material had been consumed. The solvent was removed under reduced pressure to obtain the crude product, which was used in the next step without further purification. Compound 148_4 (450 mg, 1.49 mmol, yield 82.8%, purity 90.0%) was obtained as a white solid.

[0386] 1H NMR:(400MHz,DMSO-d6)δ 11.98 (br s,2H), 3.71-3.54(m,1H), 3.28-3.10(m,2H), 2.27-2.13(m,2H), 1.90-1.67(m,3H), 1.66-1.43(m,4H), 1.42-1.35(m,9H), 1.34-1.12(m,4H)

[0387] [ka]

[0388] To a solution of compound 148_4 (450 mg, 1.66 mmol) in dioxane (5.00 mL), HCl / dioxane (5.00 mL) was added, and the solution was stirred at 25°C for 2 hours. LC-MS showed that the starting material had been consumed. The solvent was removed under reduced pressure to obtain the product. Compound 148 (200 mg, 1.14 mmol, yield 69.0%, purity 98.0%) was obtained as a yellow solid.

[0389] 1 H NMR:(400MHz,DMSO-d6)δ 12.18-11.95(m,1H), 9.45 (br d,J=1.6Hz,1H), 8.79 (br s,1H), 3.20-3.02(m,2H), 2.23 (t,J=7.3Hz,2H), 2.12-1.99(m,1H), 1.97-1.45(m,8H), 1.40-1.27(m,2H).

[0390] Example 2

[0391] Herbicide activity data

[0392] Application in weed control panels

[0393] The herbicidal activity of the compound (active ingredient, AI) was demonstrated by the following greenhouse experiment.

[0394] Implanter Low-Throughput Screening (LTP) Results

[0395] Post-emergence treatment

[0396] Basic panel of eight weed species (Table 3) sown in 4×4×7cm plastic pots containing garden mix (Klasmann). Each species was sown in a separate pot. 10-15 seeds were sown in each pot according to seed viability. The timing of application was determined at the 1-2 true leaf stage. Plants were grown for 30 days in a controlled greenhouse (26±2°C daytime, 20±2°C nighttime). Flooded irrigation (tap water + Shefer 5:3:8 8mM) was provided at a water content of 50% by weight. Two days before application, the tested plants were thinned to 3 per pot. The compound was soluble in water (DDW), and a commercially available herbicide control was soluble in formulation B (Table 4). Prior to application, 1% (v / v) crop oil and 0.02% (v / v) surfactant (Tergitol® 15-S-7) were added to the solution. Application was carried out using an industrial sprayer (TeeJet 6502E nozzle) at a rate of 2 kg / ha and a spray volume of 480 l / ha. Plants were evaluated at three time points (4, 8, and 12 days (DAA) after application). At each time point, the visual phenotype was recorded on a scale of 0 to 6 (0: no visible effect, 6: maximum effect). At 12 DAA, whole leaves of the plants were harvested, dried, and weighed for dry gravimetric analysis.

[0397] The dose-response experiments conducted after emergence included four types of herbicides: SETVI, ECHCO, AMAPA, and ABUTH (Tables 3 and 5). Applications were carried out at six different rates between 0.6 and 0.0187 kg / ha, and with a spray volume of 480 l / ha. Plants were evaluated at four time points (6, 12, 18, and 26 DAA). At each time point, the visual phenotype was recorded on a scale of 0 to 6 (0: no visible effect, 6: maximum effect). At 26 DAA, whole leaves were harvested, dried, and weighed for dry gravimetric analysis.

[0398] Wide-panel experiments conducted after emergence included 24 weed species (Table 5). Applications were carried out at two rates: 2 kg / ha and 0.25 kg / ha, and with a spray volume of 480 l / ha. Visual phenotypes were recorded at 4, 11, 17, and 20 DAA using a scale of 0-6 (0: no visible effect, 6: maximum effect). At 21 DAA, whole plant leaves were harvested, dried, and weighed for dry weight analysis. All experiments included an untreated control, a solvent control, and a positive control (commercial herbicide AI). Statistical analysis of visual phenotypes was determined by Fisher's test (p-value ≤ 0.05) with a median of ≥ 3.5. Statistical analysis of dry weights was determined by inhibition % ≥ 50 and t-test (p-value ≤ 0.05), as well as Wilcox's test (p-value ≤ 0.05).

[0399] Pre-budding treatment

[0400] Basic panels of eight weed species (Table 3) were sown in 4×4×7cm plastic pots containing inert sand (Sweet sand) and intensively washed with leachate. Each species was sown in separate pots. 10–15 seeds were sown in each pot according to seed viability. Sowing was performed one day before application. Plants were grown for 21 days in a controlled greenhouse (26±2°C daytime, 20±2°C nighttime). Flooded irrigation (tap water + Shefer 5:3:8 8mM) was provided at a water content of 50% by weight. The compounds were soluble in water (DDW), and a commercially available herbicide control was soluble in formulation B (Table 4). Application was carried out using an industrial sprayer (TeeJet 6502E nozzle) at a rate of 2 kg / ha and a spray rate of 480 l / ha.

[0401] The herbicide dose-response experiments conducted before emergence were performed at six different rates between 1 and 0.0312 kg / ha, and with a spray volume of 480 l / ha. Emergence rates were evaluated using 15 DAAs. Visual phenotypes were recorded using 18 DAAs on a scale of 0 to 6 (0: no visible effect, 6: maximum effect). All experiments included untreated controls, solvent controls, and positive controls (commercial herbicide AI). Statistical analysis of visual phenotypes was determined by Fisher's test (p-value ≤ 0.05) with a median of ≥ 3.5. Statistical analysis of plant emergence was determined by emergence % ≥ 50 and t-tests (p-value ≤ 0.05), as well as Wilcox's test (p-value ≤ 0.05).

[0402] [Table 7]

[0403] [Table 8]

[0404] [Table 9]

[0405] result:

[0406] The implant-plant low-throughput (LTP) results for compounds 104, 109, 148, 146, and 145 are shown in Table 6 below.

[0407] [Table 10-1] [Table 10-2]

[0408] The results show that compound 104 exhibits excellent control over both monocotyledonous and dicotyledonous weeds in most species tested, under both pre- and post-emergence application modes. Compound 148 shows good to moderate activity in both dicotyledonous and monocotyledonous species when applied pre-emergence. In addition, compounds 109 and 146 showed moderate inhibition of growth in dicotyledonous species when applied either pre- or post-emergence. Compound 145 showed good to moderate activity in both monocotyledonous and dicotyledonous species when applied post-emergence.

[0409] Implanter High-Throughput Screening (HTPS) Results

[0410] Post-emergence application in miniature dicotyledonous model plants

[0411] Seeds of Arabidopsis thaliana were sown in 96-well plates filled with irrigated sweet sand (10% > clay) washed with tap water to remove salt and minerals. 5-10 seeds were sown in the center of each well. 7-8 days after sowing, at the two-leaf stage, thinning was performed to ensure that compound application was performed on a single plant per well. The plates were placed in a random order in a controlled greenhouse, in a tank that could be irrigated with fertilized tap water. The applied compounds were dissolved in a final solution of 50% acetone, 49.9% DDW, and 0.1% Tween 20.

[0412] A 96-well plate was used as a stock plate to prepare application solutions for 8 replicates. Each column contained a different concentration for each chemical. The maximum concentration for application was 1.5 kg / Ha, with a dilution factor of 2.5. Chemical application was performed in a fume hood the day after thinning. 5 μL was applied to the first two true leaves in each well using a 12-channel pipette. Data collection: RGB (red, green, blue) data in the green area per well was recorded using a camera. Data was collected at several points during the experimental period: 1 day after thinning, before chemical application, and 2, 6, or 9 days after application. Visual phenotyping was performed between the last two records. Data analysis: RGB results and visual phenotypic scores were obtained, and Student's t-test was performed to compare treatment and control performance for continuous data (RGB), and Fisher's exact test was performed to analyze discontinuous data (phenotypic scores). The logarithmic concentration range of the treatment and normalized green area were used as dependent variables in the ED analysis. 50 Furthermore, dose-response curves are created for each treatment to estimate the maximum inhibitory parameter.

[0413] Pre-emergence application in dicotyledonous and monocotyledonous model plants

[0414] These experiments were carried out similarly, except that either Arabidopsis aliana or Eragrostis teff seeds were sown (5-10 or 5-7 seeds, respectively), without thinning the plants, and the compound was dissolved in a final solution of 50% acetone and 49.9% DDW. The compound was applied directly to the soil sown at a volume of 30 μL per well before plant emergence, and data were collected 10 or 7 days after chemical application to dicotyledonous or monocotyledonous plants, respectively.

[0415] Imaging, RGB, and statistical analysis

[0416] Plate imaging was performed with 11 and 18 DAAs. RGB data in the green area per well were recorded and used to extract the inhibition percentage. Dose-response curves were constructed for each treatment to estimate the EC50, EC75, and EC90 parameters, with the logarithmic concentration range of the treatment as the independent variable and the normalized green area as the dependent variable. Treatments were compared to control performance using the obtained RGB results and Student's t-test (p-value ≤ 0.05).

[0417] result:

[0418] Compounds 104-154 were applied to either or both monocotyledonous and dicotyledonous model plants in either pre-emergence, post-emergence, or both modes, according to the method described above. The compounds were applied as a concentration gradient as described above, and ED 50 I calculated it.

[0419] The results of implanter high-throughput screening (HTPS) for compounds 101-154 are shown in Table 7 below.

[0420] [Table 11]

[0421] The results in the table show excellent to very good control of most compounds (especially compound 104) in the systems in which they were tested. Compound 149 also showed very good activity in monocots. Some compounds showed weak to moderate activity in dicots.

Claims

1. The compound represented by the structure of formula I(g) below, or its pesticide-permissible salts, stereoisomers, tautomers, hydrates, isotopic variants, or any combination thereof. 【Chemistry 1】 [In the formula, R １ , R １ ', R 2', and R ４０ However, H and C are independent of each other. １ -C ５ Linear chain Branched, unsubstituted alkyl, methyl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl, benzyl, C(O)-R １０ , or C(O)-CH ３ And, R2 is CH3, R ３ is OH or NH ２ and R ４ However, NH ２ , or OH, R ３ However, if it is OH, R ４ However, NH ２ And R ３ However, NH ２ If R ４ However, it is OH, R ３ However, it is OH and R ４ However, NH ２ In that case, n+m cannot be equal to 3. or R ３ and R ４ However, they connect together to form ring A represented by the following structure, 【Chemistry 2】 R ５ However, H, C １ -C ５ Linear or branched, substituted or unsubstituted alkyl, C ２ -C ５ Linear or branched, substituted or unsubstituted alkenyls, C ２ -C ５ Linear or branched, substituted or unsubstituted alkynyl, C １ -C ５ Linear or branched haloalkyl, R ８ - Aryl, C (=CH ２ )-R １０ , substituted or unsubstituted alkyl sulfones, substituted or unsubstituted aryls, substituted or unsubstituted heteroaryls, R ８ [CH ２ ] ｐ And, p is between 1 and 10, R １０ However, H, CN, C １ -C ５ Linear or branched alkyl, C(O)R, or S(O) ２ It is R, R is C １ -C ５ Linear or branched alkyl, C １ -C ５ It is a linear or branched alkoxy, phenyl, aryl, or heteroaryl, m is 1 or 2, n is 1, 2, or 3, X １ However, it is CH2, X ２ However, it is CH2, X ３ However, O, NH, or N-R ５０ And, R 50 is H or C １ -C ５ It is a linear or branched alkyl group, substituted or unsubstituted. However, the compound is not (6R,7S)-6-amino-7-hydroxyoctanoic acid, and furthermore, the compound is not 5-((4R,5S)-5-methyl-2-oxoxazolidine-4-yl)pentanoic acid, and the substitution is selected from the group consisting of F, Cl, Br, I, OH, SH, C1-C5 linear or branched alkyl, C2-C5 linear or branched alkenyl, C2-C5 linear or branched alkynyl, C3-C8 cycloalkyl, linear, branched or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl, C3-C8 cycloalkyl, CN, NO2, or any combination thereof.

2. The compound according to claim 1, wherein ring A has two chiral centers.

3. The compound according to claim 1, wherein the compound is not (6R,7S)-6-amino-7-hydroxyoctanoic acid or 5-((4R,5S)-5-methyl-2-oxoxazolidine-4-yl)pentanoic acid.

4. The compound according to claim 1 or 2, wherein the compound is a substantially pure single stereoisomer, and the substantially pure single stereoisomer has a purity of more than 90%.

5. The compound according to claim 1 or 2, wherein the compound is a mixture of stereoisomers.

6. The compound according to any one of claims 1 to 3, wherein the compound is a substantially pure SR stereoisomer, RS stereoisomer, RR stereoisomer, or SS diastereomer, and the substantially pure SR stereoisomer, RS stereoisomer, RR stereoisomer, or SS diastereomer has a purity of more than 90%.

7. The compound according to claim 4 or 6, wherein the substantially pure single stereoisomer has a purity of more than 95%.

8. R １ and R １ ', both are H, R ２ However, CH ３ And R ２ 'but H or CH ３ And R 40 However, H or CH ３ X １ However, CH ２ X ２ However, CH ２ X ３ However, O, NH, or N-CH ３ And R ５ However, H, ethyl, butyl, CH ２ -CCH, CH ２ -C(O)-OCH ３ , or SO ２ -CH ２ - It is cyclopentyl, R ３ However, it is OH, and R ４ However, NH ２ is or R ３ and R ４ The compound according to claim 1, wherein the members are linked to form a ring A, and n is 1, m is 1, or any combination thereof.

9. The compound according to any one of claims 1 to 8, represented by any one of the following structures. Table 1

10. A compound represented by one of the following structures. Table 2-1 Table 2-2

11. A herbicide compound represented by the structure of formula I(ga) below, or a pesticide-permissible salt, stereoisomer, tautomer, hydrate, isotopic variant, or any combination thereof. 【Transformation 3】 [In the formula, C Ａ and C Ｂ However, both are chiral carbon centers, or C Ａ and C Ｂ However, R ３ and R ４ Together with the above, they form ring A represented by the following structure, 【Chemistry 4】 R １ , R １ ', R ２ , R ２ ', and R ４０ are each independently H, C １ -C ５ linear or branched, unsubstituted alkyl, methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl, benzyl, C(O)-R １０ , or C(O)-CH ３ and R ３ However, OH, SH, NH ２ NHNH ２ NHR, N(R) ２ , NHC(O)OBz, -NHC(O)-R １０ , NHC(O)CH3, R ４ is NH ２ , NHNH ２ , N(R) ２ , -NH C(O)-R １０ , NH C(O)H, NH C(O)CH3, or Or R ３ and R ４ However, they connect together to form the ring A described above. R ３ and R ４ Both are NH ２ It is not possible to be that way. R ３ However, it is OH, and R ４ However, NH ２ In that case, n+m cannot be equal to 3. R ５ However, H, C １ -C ５ Linear or branched, substituted or unsubstituted alkyl groups), C ２ -C ５ Linear or branched, substituted or unsubstituted alkenyls, C ２ -C ５ Linear or branched, substituted or unsubstituted alkynyl, C １ -C ５ Linear or branched haloalkyl, R ８ - Aryl, C (=CH ２ )-R １０ , substituted or unsubstituted alkyl sulfones, substituted or unsubstituted aryls, substituted or unsubstituted heteroaryls, R ８ [CH ２ ] ｐ And, p is between 1 and 10, R １０ and R １１ However, each is independent of H, CN, and C. １ -C ５ Linear or branched alkyl, C(O)R, or S(O) ２ Is it R? Or R １０ and R １１ However, when linked, substitution or non-substitution C ３ -C ８ Forming a complex ring, R is C １ -C ５ Linear or branched alkyl, C １ -C ５ It may be a linear or branched alkoxy, phenyl, aryl, or heteroaryl molecule, or two gem R substituents may be linked together to form a 5- or 6-membered heterocyclic ring. m is 1 or 2, n is 0, 1, 2, or 3, X １ However, S, O, or CH ２ And, X ２ However, S, O, or CH ２ And, X ３ However, O, NH, or N-R ５０ And, R 50 is H or C １ -C ５ It is a linear or branched alkyl group, substituted or unsubstituted.

12. A herbicide compound represented by one of the following structures. Table 3-1 Table 3-2

13. The compound according to any one of claims 1 to 12, wherein the compound is a substantially pure single stereoisomer, and the substantially pure single stereoisomer has a purity of more than 90%.

14. The compound according to any one of claims 1 to 13, wherein the substantially pure stereoisomer has a purity of more than 95%.

15. A compound according to any one of claims 1 to 14, for use in controlling undesirable plant growth.

16. The compound according to claim 15, wherein the plant is a true dicotyledonous plant (dicotyl) or a monocotyledonous plant (monocotyl).

17. The compound according to claim 15 or 16, wherein the plant is a weed.

18. The weeds are Abutilon theophrasti, Amaranthus palmeri, Ambrosia artemisiifolia, Alopecurus myosuroides, Avena. sterilis, Chenopodium album, Conyza Canadensis, Digitalia sanguinalis, Echinochloa colona, ​​Euphorbia heterophylla, Lolium perenne, Lolium rigidum, Matricaria chamomilla, Phalaris paradoxa, Poa annua, Portulaca The compound according to claim 17, comprising oleracea, Setaria viridis, Solanum nigrum, or any combination thereof.

19. The compound according to claim 16, wherein the dicotyledonous plant is Arabidopsis thaliana and / or the monocotyledonous plant is Dactyloctenium aegyptium or Eragrostis teff.

20. A compound according to any one of claims 1 to 14 for use in pre-planting treatment, pre-emergence treatment, post-emergence treatment, or any combination thereof.

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