Pesticidal and Herbicidal Compounds and Methods of Using Them - Patent application

Abstract

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

Description

[Technical field]

[0001] The present invention relates to novel pesticidally and / or herbicidally active compounds, agrochemical compositions thereof, processes for their preparation and their use for controlling the growth of undesirable plants (e.g. weeds), for example in crop fields. [Background technology]

[0002] Weeds often impede 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 unpleasant, especially when they appear within a colony of desirable plants, such as St. Augustine grass or Kentucky bluegrass in a homeowner's lawn. Weeds can also impede visibility, pose fire hazards around buildings, and reduce the efficiency of irrigation systems. When weeds appear in waterways, such as rivers and lakes, they contribute to a decline in water quality, making the water unsuitable for culinary and industrial use. Additionally, some weeds act in a toxic manner to other plants, animals, and humans, by secreting toxic substances known as allelopathic compounds, or by diffusing agents that can cause allergies and / or disease. Finally, weeds provide refuge for insects and rodents that spread disease or are otherwise harmful to desirable plants, animals, or humans.

[0003] Weeds cause agricultural losses to crops that consistently exceed those caused by other classes of agricultural pests annually. In addition to reducing crop quality, weed infestation can reduce achievable crop yields by up to 100% of theoretically achievable yields. Many approaches have evolved to control weed infestation, including mechanical, agronomic, biological, and chemical techniques.

[0004] Mechanical means such as hand-pulling, plowing or tilling, deep plowing, mowing, cutting, burning, and / or mulching may be used in an attempt to eradicate or control weeds. Cover crops can also be planted to cover the ground when more valuable crops are not being grown, thus typically minimizing the weed infestation that would normally be expected in bare areas. Crop rotation and planting of "suppression" crops that are adapted to grow more vigorously than the weeds have also been attempted as a 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 feed on the weeds, thereby reducing the weed population.

[0005] Mechanical, agronomic, and biological methods of weed control sometimes help reduce the level of weed infestation, but are not entirely satisfactory. First, mechanical and agronomic techniques are fairly 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 agronomic techniques. Similarly, biological techniques, such as the introduction of populations of predators, are not entirely satisfactory, as the predators may not be selective for only weed populations.

[0006] Chemically active herbicides represent another potential weed control technique. These chemical herbicides can be classified as pre-emergence and post-emergence herbicides. Pre-emergence herbicides usually prevent weed seeds from germinating, while post-emergence herbicides kill weeds after the weed seeds have germinated and weed growth has commenced.

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

[0008] Many pre-emergence and post-emergence herbicides also suffer from other problems. Specifically, many pre-emergence and post-emergence herbicides are either moderately or highly toxic to humans and animals, and thus may have harmful effects far beyond the intended weed control effect. Toxic herbicides may cause either immediate or long-term harm to the humans applying the herbicide and to those present when the herbicide is applied. Also, residual concentrations of toxic herbicides remaining in soil or water after herbicide application may pose a serious threat to humans and animals, including terrestrial animals and amphibians, as well as fish, in contact with or runoff from the treated area. Furthermore, public anxiety regarding the use of toxic chemicals as herbicides and their possible widespread and long-term effects on the quality of the environment demands that the continued use of these toxic herbicides be opposed. Summary of the Invention [Problem to be solved by the invention]

[0009] There is a need for a pesticidal and / or herbicidal solution that avoids the critical timing problem of pre-emergence herbicide application.In addition, there is a need for a pesticidal and / or herbicidal solution that avoids the toxic effects of currently available pre-emergence and post-emergence herbicides on humans, animals, and generally the environment.In addition, there is a need for an economically efficient post-emergence weed technique that selectively controls weeds without destroying or hindering the growth of desired plants.In addition, there is a need for a composition that reduces the amount of herbicide required to obtain sufficient weed control while minimizing damage to crop plants.

[0010] As more weeds become resistant to herbicides, alternative compositions with high weed control are desired.Furthermore, as no-tillage cultivation continues to gain popularity, there is a greater need for effective herbicides.Compositions with effective weed control and low application rates lead to increased crop yields and reduced environmental, human and mammalian health concerns. [Means for solving the problem]

[0011] In various embodiments, the present invention is directed to compounds represented by the structures of Formula I, II(a)-II(d), and III(a)-III(c) as defined below, or a pesticidally acceptable salt, zwitterion (inner salt), stereoisomer, tautomer, hydrate, N-oxide, reverse amide analog, isotopic variant (e.g., deuterated analog), or any combination thereof.

[0012] In various embodiments, the present invention is directed to compounds having a structure according to Formula I, depicted below, where at least one of the A, B and C rings is absent.

[0013] In various embodiments, the present invention is directed to a compound represented by the structure of Formula I, as set forth below, wherein one of R3 and R4 is NH2 and the other is OH.

[0014] In various embodiments, the present invention is directed to compounds represented by the structure of Formula I, depicted below, where at least one of R3 and R4 is NH2.

[0015] In some embodiments, the compound is not (E)-7-aminooct-4-enoic acid. In some embodiments, the compound is not 7-aminooct-4-enoic acid. In some embodiments, the compound is represented by the structure of Formula II(a), II(b), II(c), II(d), III(a), III(b), or III(c), as set forth below. In some embodiments, R 20 is F or methyl. In some embodiments, R1 is H and R2 is CH3 or CH2CH3, or R1 and R2 combine to form cyclohexyl. In some embodiments, R2' is H or CH3 and R3 is H, OH or NH2, or R3 and R2' combine to form cyclopropyl. In some embodiments, R4 is H or NH2. In some embodiments, R 40 is H and R is H, OH or NH2, or R and R 40 are linked to form a 3-8 membered cycloalkyl ring. In some embodiments, X1 is O. In some embodiments, R5 is H.

[0016] In some embodiments, the compound is a substantially pure single stereoisomer. In some embodiments, the substantially pure stereoisomer has a purity of greater than 90%. In some embodiments, the substantially pure stereoisomer has a purity of greater than 95%. In some embodiments, the substantially pure stereoisomer has a purity of greater than 98%. In some embodiments, the compound is any of the compounds set forth in Table 1 below, or a pesticidally acceptable salt, zwitterion (inner salt), stereoisomer, tautomer, hydrate, N-oxide, reverse amide analog, or isotopic variant thereof; each of which represents a separate embodiment according to the present invention. In some embodiments, the compound is a herbicide, a pesticide, or a combination thereof.

[0017] In various embodiments, the present invention is directed to an agricultural chemical composition comprising a compound of the present invention and a pesticidally acceptable carrier or diluent.

[0018] In various embodiments, the present invention is directed to pesticidal and / or herbicidal compounds represented by the structures of Formula I, II(a)-II(d) and III(a)-III(c) as defined below, or a pesticidally acceptable salt, zwitterion (inner salt), stereoisomer, tautomer, hydrate, N-oxide, reverse amide analogue or isotopic variant (e.g., deuterated analogue) thereof; each of which represents a separate embodiment according to the present invention.

[0019] In various embodiments, the present invention is directed to an agricultural chemical composition comprising a pesticidally and / or herbicidally effective amount of a compound according to the present invention.

[0020] In various embodiments, the present invention is directed to a method for controlling undesirable plant growth, wherein the method comprises applying to a field of a useful crop a compound according to the present invention or an agrochemical composition according to the present invention.

[0021] In various embodiments, the present invention is directed to a compound according to the present invention or an agrochemical composition according to the present invention for use in controlling the growth of undesirable plants.In some embodiments, the plant is a dicotyledonous plant or a monocotyledonous plant.In some embodiments, the foodstuff is a weed. In some embodiments, the weeds are Abutilon theophrasti, Amaranthus palmeri, Ambrosia artemisiifolia, Alopecurus myosuroides, Avena sterilis, Chenopodium album, Conyza Canadensis, Digitaria sanguinalis, Echinochloa colona, ​​Euphorbia heterophylla, Lolium perenne, Lolium rigidum, Matricaria chamomilla, Phalaris paradoxa, Poa annua, or the like. In some embodiments, the dicotyledonous plant is Arabidopsis thaliana, and / or the monocotyledonous plant is Dactyloctenium aegyptium or Eragrostis teff. In some embodiments, the compound is for use in pre-planting, pre-emergence, post-emergence, or any combination thereof; each of which represents a separate embodiment according to the present invention. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0022] In various embodiments, the present invention provides a compound of formula (I): [ka] [During the ceremony, C I , C II , C III and C IV are each independently an sp carbon atom, an sp 2 Carbon atom or sp 3 and, respectively, sp carbon atom; sp 2 Carbon atom; or sp 3 For carbon atoms, each independently is C; CH or CR 20 ; or CH2, CHR 20 Or C(R 20 )2; Here, R 20 is halogen (e.g., F) or C1-C5 linear or branched alkyl (e.g., methyl); C I …C II , C II …C III , C III …C IV are each independently a single bond or a double bond, where C I …C II , C II …C III and C III …C IV at least one of is a double bond; or C I …C II , C II …C III and C III …C IV are each independently a single bond or a triple bond, where C I …C II , C II …C III and C III …C IV at least one of is a triple bond; R1 is H, F, Cl, Br, I, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl, benzyl); Here, C I …C II is a triple bond, then R1 is absent; R2 is H, F, Cl, Br, I, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl), C2-C5 straight or branched chain substituted or unsubstituted alkenyl (e.g., ethenyl (CH=CH2)), C2-C5 straight or branched chain substituted or unsubstituted alkynyl (e.g., ethynyl (CCH)); Or, R1 and R2 combine together to form a 3-8 membered substituted or unsubstituted saturated or unsaturated carbocyclic ring B (e.g., cyclohexyl, cyclohexenyl, cyclopentyl); R2' is H, F, Cl, Br, I, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl), C2-C5 straight or branched chain substituted or unsubstituted alkenyl (e.g., ethenyl (CH=CH2)), C2-C5 straight or branched chain substituted or unsubstituted alkynyl (e.g., ethynyl (CCH)); R3 is H, F, Cl, Br, I, OH, SH, NH2, NHR, N(R)2; Or, R3 and R2' combine to form a 3-8 membered substituted or unsubstituted cycloalkyl ring C (e.g., cyclopropyl); R4 is H, F, Cl, Br, I, OH, SH, NH2, NHR, N(R)2; R 40is H, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl); Or, R3 and R 40 are joined together to form a 3-8 membered substituted or unsubstituted cycloalkyl ring A (e.g., cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl); Or, R4 and R 40 combine to form a 3-8 membered substituted or unsubstituted heterocyclic or cycloalkyl ring; 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 alkylsulfone (e.g., SO2-CH2-cyclopropyl), substituted or unsubstituted aryl (e.g., phenyl), substituted or unsubstituted heteroaryl (e.g., pyridine (2, 3, and 4-pyridine); X1 is O, CH2, NH or NR 50 and; R8 is [CH2] p and; where p is 1 to 10; R 10is H, CN, C1-C5 straight or branched chain alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH3)), or S(O)2R; R 50 is H, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, butyl, i-propyl); R is a C1-C5 straight or branched chain alkyl, a C1-C5 straight or branched chain alkoxy, a phenyl, an aryl, or a heteroaryl, or two geminal R substituents are joined together to form a 5- or 6-membered heterocyclic ring; Ring A is absent or a 3-8 membered substituted or unsubstituted cycloalkyl ring (e.g., cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl); Ring B is absent or a 3-8 membered substituted or unsubstituted saturated or unsaturated carbocyclic ring (e.g., cyclohexyl, cyclohexenyl, cyclopentyl); Ring C is absent or is a 3- to 8-membered substituted or unsubstituted cycloalkyl ring (e.g., cyclopropyl). or a pesticidally acceptable salt, zwitterion (inner salt), stereoisomer, tautomer, hydrate, N-oxide, reverse amide analog, isotopic variant (e.g., deuterated analog), or any combination thereof.

[0023] In some embodiments, at least one of R3 and R4 is NH2. In some embodiments, at least one of the A, B, and C rings is present. In some embodiments, one of R3 and R4 is NH2 and the other is OH. In some embodiments, the compound is not (E)-7-aminooct-4-enoic acid. In some embodiments, the compound is not 7-aminooct-4-enoic acid. In some embodiments, the compound is a substantially pure single stereoisomer.

[0024] In some embodiments, the compound is any one of the compounds listed in Table 1. In various embodiments, the compound is a herbicidal compound. In various embodiments, the compound is for use in controlling undesirable plant growth. In various embodiments, the compound is a pesticide. In various embodiments, the compound is a pesticidal compound.

[0025] In various embodiments, the compound of formula I is represented by any one of the structures depicted in Table 1. [Table 1] In various embodiments, the present invention provides a compound represented by formula II(a): [ka] [During the ceremony, R', R'', and R''' are each independently selected from halogen (e.g., F) or C1-C5 straight or branched alkyl (e.g., methyl); R1 is H, F, Cl, Br, I, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl, benzyl); R2 is H, F, Cl, Br, I, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl), C2-C5 straight or branched chain substituted or unsubstituted alkenyl (e.g., ethenyl (CH=CH2)), C2-C5 straight or branched chain substituted or unsubstituted alkynyl (e.g., ethynyl (CCH)); Or, R1 and R2 combine together to form a 3-8 membered substituted or unsubstituted saturated or unsaturated carbocyclic ring B (e.g., cyclohexyl, cyclohexenyl, cyclopentyl); R2' is H, F, Cl, Br, I, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl), C2-C5 straight or branched chain substituted or unsubstituted alkenyl (e.g., ethenyl (CH=CH2)), C2-C5 straight or branched chain substituted or unsubstituted alkynyl (e.g., ethynyl (CCH)); R3 is H, F, Cl, Br, I, OH, SH, NH2, NHR, N(R)2; Or, R3 and R2' combine to form a 3-8 membered substituted or unsubstituted cycloalkyl ring C (e.g., cyclopropyl); R4 is H, F, Cl, Br, I, OH, SH, NH2, NHR, N(R)2; R 40 is H, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl); Or, R3 and R 40are joined together to form a 3-8 membered substituted or unsubstituted cycloalkyl ring A (e.g., cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl); Or, R4 and R 40 combine to form a 3-8 membered substituted or unsubstituted heterocyclic or cycloalkyl ring; 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 alkylsulfone (e.g., SO2-CH2-cyclopropyl), substituted or unsubstituted aryl (e.g., phenyl), substituted or unsubstituted heteroaryl (e.g., pyridine (2, 3, and 4-pyridine); X1 is O, CH2, NH or NR 50 and; R8 is [CH2] p and; where p is 1 to 10; R 10 is H, CN, C1-C5 straight or branched chain alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH3)), or S(O)2R; R 50is H, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, butyl, i-propyl); R is a C1-C5 straight or branched chain alkyl, a C1-C5 straight or branched chain alkoxy, a phenyl, an aryl, or a heteroaryl, or two geminal R substituents are joined together to form a 5- or 6-membered heterocyclic ring; Ring A is absent or a 3-8 membered substituted or unsubstituted cycloalkyl ring (e.g., cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl); Ring B is absent or a 3-8 membered substituted or unsubstituted saturated or unsaturated carbocyclic ring (e.g., cyclohexyl, cyclohexenyl, cyclopentyl); Ring C is absent or is a 3- to 8-membered substituted or unsubstituted cycloalkyl ring (e.g., cyclopropyl). or a pesticidally acceptable salt, zwitterion (inner salt), stereoisomer, tautomer, hydrate, N-oxide, reverse amide analog, isotopic variant (e.g., deuterated analog), or any combination thereof.

[0026] In some embodiments, at least one of R3 and R4 is NH2. In some embodiments, at least one of the A, B, and C rings is present. In some embodiments, one of R3 and R4 is NH2 and the other is OH.

[0027] In some embodiments, the compound is any one of the compounds listed in Table 1. In various embodiments, the compound is a herbicidal compound. In various embodiments, the compound is for use in controlling undesirable plant growth. In various embodiments, the compound is a pesticide. In various embodiments, the compound is a pesticidal compound.

[0028] In various embodiments, the compound of formula II(a) is represented by any one of the following structures: [Table 2] In various embodiments, the present invention provides a compound of formula II(b): [ka] [During the ceremony, R', R'', and R''' are each independently selected from halogen (e.g., F) or C1-C5 straight or branched alkyl (e.g., methyl); R1 is H, F, Cl, Br, I, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl, benzyl); R2 is H, F, Cl, Br, I, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl), C2-C5 straight or branched chain substituted or unsubstituted alkenyl (e.g., ethenyl (CH=CH2)), C2-C5 straight or branched chain substituted or unsubstituted alkynyl (e.g., ethynyl (CCH)); Or, R1 and R2 combine together to form a 3-8 membered substituted or unsubstituted saturated or unsaturated carbocyclic ring B (e.g., cyclohexyl, cyclohexenyl, cyclopentyl); R2' is H, F, Cl, Br, I, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl), C2-C5 straight or branched chain substituted or unsubstituted alkenyl (e.g., ethenyl (CH=CH2)), C2-C5 straight or branched chain substituted or unsubstituted alkynyl (e.g., ethynyl (CCH)); R3 is H, F, Cl, Br, I, OH, SH, NH2, NHR, N(R)2; Or, R3 and R2' combine to form a 3-8 membered substituted or unsubstituted cycloalkyl ring C (e.g., cyclopropyl); R4 is H, F, Cl, Br, I, OH, SH, NH2, NHR, N(R)2; R 40 is H, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl); Or, R3 and R 40 are joined together to form a 3-8 membered substituted or unsubstituted cycloalkyl ring A (e.g., cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl); Or, R4 and R 40 combine to form a 3-8 membered substituted or unsubstituted heterocyclic or cycloalkyl ring; 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 alkylsulfone (e.g., SO2-CH2-cyclopropyl), substituted or unsubstituted aryl (e.g., phenyl), substituted or unsubstituted heteroaryl (e.g., pyridine (2, 3, and 4-pyridine); X1 is O, CH2, NH or NR 50 and; R8 is [CH2] p and; where p is 1 to 10; R 10 is H, CN, C1-C5 straight or branched chain alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH3)), or S(O)2R; R 50 is H, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, butyl, i-propyl); R is a C1-C5 straight or branched chain alkyl, a C1-C5 straight or branched chain alkoxy, a phenyl, an aryl, or a heteroaryl, or two geminal R substituents are joined together to form a 5- or 6-membered heterocyclic ring; Ring A is absent or a 3-8 membered substituted or unsubstituted cycloalkyl ring (e.g., cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl); Ring B is absent or a 3-8 membered substituted or unsubstituted saturated or unsaturated carbocyclic ring (e.g., cyclohexyl, cyclohexenyl, cyclopentyl); Ring C is absent or is a 3- to 8-membered substituted or unsubstituted cycloalkyl ring (e.g., cyclopropyl). or a pesticidally acceptable salt, zwitterion (inner salt), stereoisomer, tautomer, hydrate, N-oxide, reverse amide analog, isotopic variant (e.g., deuterated analog), or any combination thereof.

[0029] In some embodiments, at least one of R3 and R4 is NH2. In some embodiments, at least one of the A, B, and C rings is present. In some embodiments, one of R3 and R4 is NH2 and the other is OH.

[0030] In some embodiments, the compound is any one of the compounds listed in Table 1. In various embodiments, the compound is a herbicidal compound. In various embodiments, the compound is for use in controlling undesirable plant growth. In various embodiments, the compound is a pesticide. In various embodiments, the compound is a pesticidal compound.

[0031] In various embodiments, the compound of formula II(b) is represented by any one of the following structures: [Table 3] TIFF2025510687000011.tif154132 In various embodiments, the present invention provides a compound of formula II(c): [ka] [During the ceremony, R', R'', and R''' are each independently selected from halogen (e.g., F) or C1-C5 straight or branched alkyl (e.g., methyl); R1 is H, F, Cl, Br, I, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl, benzyl); R2 is H, F, Cl, Br, I, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl), C2-C5 straight or branched chain substituted or unsubstituted alkenyl (e.g., ethenyl (CH=CH2)), C2-C5 straight or branched chain substituted or unsubstituted alkynyl (e.g., ethynyl (CCH)); Or, R1 and R2 combine together to form a 3-8 membered substituted or unsubstituted saturated or unsaturated carbocyclic ring B (e.g., cyclohexyl, cyclohexenyl, cyclopentyl); R2' is H, F, Cl, Br, I, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl), C2-C5 straight or branched chain substituted or unsubstituted alkenyl (e.g., ethenyl (CH=CH2)), C2-C5 straight or branched chain substituted or unsubstituted alkynyl (e.g., ethynyl (CCH)); R3 is H, F, Cl, Br, I, OH, SH, NH2, NHR, N(R)2; Or, R3 and R2' combine to form a 3-8 membered substituted or unsubstituted cycloalkyl ring C (e.g., cyclopropyl); R4 is H, F, Cl, Br, I, OH, SH, NH2, NHR, N(R)2; R 40 is H, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl); Or, R3 and R 40 are joined together to form a 3-8 membered substituted or unsubstituted cycloalkyl ring A (e.g., cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl); Or, R4 and R 40 combine to form a 3-8 membered substituted or unsubstituted heterocyclic or cycloalkyl ring; 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 alkylsulfone (e.g., SO2-CH2-cyclopropyl), substituted or unsubstituted aryl (e.g., phenyl), substituted or unsubstituted heteroaryl (e.g., pyridine (2, 3, and 4-pyridine); X1 is O, CH2, NH or NR 50 and; R8 is [CH2] p and; where p is 1 to 10; R 10 is H, CN, C1-C5 straight or branched chain alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH3)), or S(O)2R; R 50 is H, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, butyl, i-propyl); R is a C1-C5 straight or branched chain alkyl, a C1-C5 straight or branched chain alkoxy, a phenyl, an aryl, or a heteroaryl, or two geminal R substituents are joined together to form a 5- or 6-membered heterocyclic ring; Ring A is absent or a 3-8 membered substituted or unsubstituted cycloalkyl ring (e.g., cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl); Ring B is absent or a 3-8 membered substituted or unsubstituted saturated or unsaturated carbocyclic ring (e.g., cyclohexyl, cyclohexenyl, cyclopentyl); Ring C is absent or is a 3- to 8-membered substituted or unsubstituted cycloalkyl ring (e.g., cyclopropyl). or a pesticidally acceptable salt, zwitterion (inner salt), stereoisomer, tautomer, hydrate, N-oxide, reverse amide analog, isotopic variant (e.g., deuterated analog), or any combination thereof.

[0032] In some embodiments, at least one of R3 and R4 is NH2. In some embodiments, at least one of the A, B, and C rings is present. In some embodiments, one of R3 and R4 is NH2 and the other is OH.

[0033] In some embodiments, the compound is not (E)-7-aminooct-4-enoic acid. In some embodiments, the compound is not 7-aminooct-4-enoic acid.

[0034] In some embodiments, the compound is any one of the compounds listed in Table 1. In various embodiments, the compound is a herbicidal compound. In various embodiments, the compound is for use in controlling undesirable plant growth. In various embodiments, the compound is a pesticide. In various embodiments, the compound is a pesticidal compound.

[0035] In various embodiments, the compound of formula II(c) is represented by any one of the following structures: [Table 4] In various embodiments, the present invention provides a compound of formula II(d): [ka] [During the ceremony, R', R'', and R''' are each independently selected from halogen (e.g., F) or C1-C5 straight or branched alkyl (e.g., methyl); R1 is H, F, Cl, Br, I, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl, benzyl); R2 is H, F, Cl, Br, I, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl), C2-C5 straight or branched chain substituted or unsubstituted alkenyl (e.g., ethenyl (CH=CH2)), C2-C5 straight or branched chain substituted or unsubstituted alkynyl (e.g., ethynyl (CCH)); Or, R1 and R2 combine together to form a 3-8 membered substituted or unsubstituted saturated or unsaturated carbocyclic ring B (e.g., cyclohexyl, cyclohexenyl, cyclopentyl); R2' is H, F, Cl, Br, I, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl), C2-C5 straight or branched chain substituted or unsubstituted alkenyl (e.g., ethenyl (CH=CH2)), C2-C5 straight or branched chain substituted or unsubstituted alkynyl (e.g., ethynyl (CCH)); R3 is H, F, Cl, Br, I, OH, SH, NH2, NHR, N(R)2; Or, R3 and R2' combine to form a 3-8 membered substituted or unsubstituted cycloalkyl ring C (e.g., cyclopropyl); R4 is H, F, Cl, Br, I, OH, SH, NH2, NHR, N(R)2; R 40 is H, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl); Or, R3 and R 40are joined together to form a 3-8 membered substituted or unsubstituted cycloalkyl ring A (e.g., cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl); Or, R4 and R 40 combine to form a 3-8 membered substituted or unsubstituted heterocyclic or cycloalkyl ring; 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 alkylsulfone (e.g., SO2-CH2-cyclopropyl), substituted or unsubstituted aryl (e.g., phenyl), substituted or unsubstituted heteroaryl (e.g., pyridine (2, 3, and 4-pyridine); X1 is O, CH2, NH or NR 50 and; R8 is [CH2] p and; where p is 1 to 10; R 10 is H, CN, C1-C5 straight or branched chain alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH3)), or S(O)2R; R 50is H, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, butyl, i-propyl); R is a C1-C5 straight or branched chain alkyl, a C1-C5 straight or branched chain alkoxy, a phenyl, an aryl, or a heteroaryl, or two geminal R substituents are joined together to form a 5- or 6-membered heterocyclic ring; Ring A is absent or a 3-8 membered substituted or unsubstituted cycloalkyl ring (e.g., cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl); Ring B is absent or a 3-8 membered substituted or unsubstituted saturated or unsaturated carbocyclic ring (e.g., cyclohexyl, cyclohexenyl, cyclopentyl); Ring C is absent or is a 3- to 8-membered substituted or unsubstituted cycloalkyl ring (e.g., cyclopropyl). or a pesticidally acceptable salt, zwitterion (inner salt), stereoisomer, tautomer, hydrate, N-oxide, reverse amide analog, isotopic variant (e.g., deuterated analog), or any combination thereof.

[0036] In some embodiments, at least one of R3 and R4 is NH2. In some embodiments, at least one of the A, B, and C rings is present. In some embodiments, one of R3 and R4 is NH2 and the other is OH.

[0037] In some embodiments, the compound is any one of the compounds listed in Table 1. In various embodiments, the compound is a herbicidal compound. In various embodiments, the compound is for use in controlling undesirable plant growth. In various embodiments, the compound is a pesticide. In various embodiments, the compound is a pesticidal compound.

[0038] In various embodiments, the compound of formula II(d) is represented by any one of the following structures: [Table 5] In various embodiments, the present invention provides a compound of formula III(a): [ka] [During the ceremony, R''' is halogen (e.g., F) or C1-C5 straight or branched alkyl (e.g., methyl); R1 is H, F, Cl, Br, I, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl, benzyl); R2 is H, F, Cl, Br, I, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl), C2-C5 straight or branched chain substituted or unsubstituted alkenyl (e.g., ethenyl (CH=CH2)), C2-C5 straight or branched chain substituted or unsubstituted alkynyl (e.g., ethynyl (CCH)); Or, R1 and R2 combine together to form a 3-8 membered substituted or unsubstituted saturated or unsaturated carbocyclic ring B (e.g., cyclohexyl, cyclohexenyl, cyclopentyl); R2' is H, F, Cl, Br, I, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl), C2-C5 straight or branched chain substituted or unsubstituted alkenyl (e.g., ethenyl (CH=CH2)), C2-C5 straight or branched chain substituted or unsubstituted alkynyl (e.g., ethynyl (CCH)); R3 is H, F, Cl, Br, I, OH, SH, NH2, NHR, N(R)2; Or, R3 and R2' combine to form a 3-8 membered substituted or unsubstituted cycloalkyl ring C (e.g., cyclopropyl); R4 is H, F, Cl, Br, I, OH, SH, NH2, NHR, N(R)2; R 40 is H, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl); Or, R3 and R 40 are joined together to form a 3-8 membered substituted or unsubstituted cycloalkyl ring A (e.g., cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl); Or, R4 and R 40 combine to form a 3-8 membered substituted or unsubstituted heterocyclic or cycloalkyl ring; 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 alkylsulfone (e.g., SO2-CH2-cyclopropyl), substituted or unsubstituted aryl (e.g., phenyl), substituted or unsubstituted heteroaryl (e.g., pyridine (2, 3, and 4-pyridine); X1 is O, CH2, NH or NR 50 and; R8 is [CH2] p and; where p is 1 to 10; R 10 is H, CN, C1-C5 straight or branched chain alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH3)), or S(O)2R; R 50 is H, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, butyl, i-propyl); R is a C1-C5 straight or branched chain alkyl, a C1-C5 straight or branched chain alkoxy, a phenyl, an aryl, or a heteroaryl, or two geminal R substituents are joined together to form a 5- or 6-membered heterocyclic ring; Ring A is absent or a 3-8 membered substituted or unsubstituted cycloalkyl ring (e.g., cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl); Ring B is absent or a 3-8 membered substituted or unsubstituted saturated or unsaturated carbocyclic ring (e.g., cyclohexyl, cyclohexenyl, cyclopentyl); Ring C is absent or is a 3- to 8-membered substituted or unsubstituted cycloalkyl ring (e.g., cyclopropyl). or a pesticidally acceptable salt, zwitterion (inner salt), stereoisomer, tautomer, hydrate, N-oxide, reverse amide analog, isotopic variant (e.g., deuterated analog), or any combination thereof.

[0039] In some embodiments, at least one of R3 and R4 is NH2. In some embodiments, at least one of the A, B, and C rings is present. In some embodiments, one of R3 and R4 is NH2 and the other is OH.

[0040] In some embodiments, the compound is any one of the compounds listed in Table 1. In various embodiments, the compound is a herbicidal compound. In various embodiments, the compound is for use in controlling undesirable plant growth. In various embodiments, the compound is a pesticide. In various embodiments, the compound is a pesticidal compound.

[0041] In various embodiments, the compound of formula III(a) is represented by any one of the following structures: [Table 6] In various embodiments, the present invention provides a compound of formula III(b): [ka] [During the ceremony, R' is halogen (e.g., F) or C1-C5 straight or branched alkyl (e.g., methyl); R1 is H, F, Cl, Br, I, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl, benzyl); R2 is H, F, Cl, Br, I, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl), C2-C5 straight or branched chain substituted or unsubstituted alkenyl (e.g., ethenyl (CH=CH2)), C2-C5 straight or branched chain substituted or unsubstituted alkynyl (e.g., ethynyl (CCH)); Or, R1 and R2 combine together to form a 3-8 membered substituted or unsubstituted saturated or unsaturated carbocyclic ring B (e.g., cyclohexyl, cyclohexenyl, cyclopentyl); R2' is H, F, Cl, Br, I, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl), C2-C5 straight or branched chain substituted or unsubstituted alkenyl (e.g., ethenyl (CH=CH2)), C2-C5 straight or branched chain substituted or unsubstituted alkynyl (e.g., ethynyl (CCH)); R3 is H, F, Cl, Br, I, OH, SH, NH2, NHR, N(R)2; Or, R3 and R2' combine to form a 3-8 membered substituted or unsubstituted cycloalkyl ring C (e.g., cyclopropyl); R4 is H, F, Cl, Br, I, OH, SH, NH2, NHR, N(R)2; R 40 is H, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl); Or, R3 and R 40 are joined together to form a 3-8 membered substituted or unsubstituted cycloalkyl ring A (e.g., cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl); Or, R4 and R 40 combine to form a 3-8 membered substituted or unsubstituted heterocyclic or cycloalkyl ring; 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 alkylsulfone (e.g., SO2-CH2-cyclopropyl), substituted or unsubstituted aryl (e.g., phenyl), substituted or unsubstituted heteroaryl (e.g., pyridine (2, 3, and 4-pyridine); X1 is O, CH2, NH or NR 50 and; R8 is [CH2] pand; where p is 1 to 10; R 10 is H, CN, C1-C5 straight or branched chain alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH3)), or S(O)2R; R 50 is H, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, butyl, i-propyl); R is a C1-C5 straight or branched chain alkyl, a C1-C5 straight or branched chain alkoxy, a phenyl, an aryl, or a heteroaryl, or two geminal R substituents are joined together to form a 5- or 6-membered heterocyclic ring; Ring A is absent or a 3-8 membered substituted or unsubstituted cycloalkyl ring (e.g., cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl); Ring B is absent or a 3-8 membered substituted or unsubstituted saturated or unsaturated carbocyclic ring (e.g., cyclohexyl, cyclohexenyl, cyclopentyl); Ring C is absent or is a 3- to 8-membered substituted or unsubstituted cycloalkyl ring (e.g., cyclopropyl). or a pesticidally acceptable salt, zwitterion (inner salt), stereoisomer, tautomer, hydrate, N-oxide, reverse amide analog, isotopic variant (e.g., deuterated analog), or any combination thereof.

[0042] In some embodiments, at least one of R3 and R4 is NH2. In some embodiments, at least one of the A, B, and C rings is present. In some embodiments, one of R3 and R4 is NH2 and the other is OH.

[0043] In some embodiments, the compound is any one of the compounds listed in Table 1. In various embodiments, the compound is a herbicidal compound. In various embodiments, the compound is for use in controlling undesirable plant growth. In various embodiments, the compound is a pesticide. In various embodiments, the compound is a pesticidal compound.

[0044] In various embodiments, the compound of formula III(b) is represented by any one of the following structures: [Table 7] In various embodiments, the present invention provides a compound of formula III(c): [ka] [During the ceremony, R' and R'' are each independently selected from halogen (e.g., F) or C1-C5 straight or branched alkyl (e.g., methyl); R2 is H, F, Cl, Br, I, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl), C2-C5 straight or branched chain substituted or unsubstituted alkenyl (e.g., ethenyl (CH=CH2)), C2-C5 straight or branched chain substituted or unsubstituted alkynyl (e.g., ethynyl (CCH)); R2' is H, F, Cl, Br, I, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl), C2-C5 straight or branched chain substituted or unsubstituted alkenyl (e.g., ethenyl (CH=CH2)), C2-C5 straight or branched chain substituted or unsubstituted alkynyl (e.g., ethynyl (CCH)); R3 is H, F, Cl, Br, I, OH, SH, NH2, NHR, N(R)2; Or, R3 and R2' combine to form a 3-8 membered substituted or unsubstituted cycloalkyl ring C (e.g., cyclopropyl); R4 is H, F, Cl, Br, I, OH, SH, NH2, NHR, N(R)2; R 40 is H, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl); Or, R3 and R 40 are joined together to form a 3-8 membered substituted or unsubstituted cycloalkyl ring A (e.g., cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl); Or, R4 and R 40 combine to form a 3-8 membered substituted or unsubstituted heterocyclic or cycloalkyl ring; 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 alkylsulfone (e.g., SO2-CH2-cyclopropyl), substituted or unsubstituted aryl (e.g., phenyl), substituted or unsubstituted heteroaryl (e.g., pyridine (2, 3, and 4-pyridine); X1 is O, CH2, NH or NR 50 and; R8 is [CH2] p and; where p is 1 to 10; R 10 is H, CN, C1-C5 straight or branched chain alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH3)), or S(O)2R; R 50 is H, C1-C5 straight or branched chain substituted or unsubstituted alkyl (e.g., methyl, ethyl, butyl, i-propyl); R is a C1-C5 straight or branched chain alkyl, a C1-C5 straight or branched chain alkoxy, a phenyl, an aryl, or a heteroaryl, or two geminal R substituents are joined together to form a 5- or 6-membered heterocyclic ring; Ring A is absent or a 3-8 membered substituted or unsubstituted cycloalkyl ring (e.g., cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl); Ring C is absent or is a 3- to 8-membered substituted or unsubstituted cycloalkyl ring (e.g., cyclopropyl). or a pesticidally acceptable salt, zwitterion (inner salt), stereoisomer, tautomer, hydrate, N-oxide, reverse amide analog, isotopic variant (e.g., deuterated analog), or any combination thereof.

[0045] In some embodiments, at least one of R3 and R4 is NH2. In some embodiments, at least one of the A, B, and C rings is present. In some embodiments, one of R3 and R4 is NH2 and the other is OH.

[0046] In some embodiments, the compound is any one of the compounds listed in Table 1. In various embodiments, the compound is a herbicidal compound. In various embodiments, the compound is for use in controlling undesirable plant growth. In various embodiments, the compound is a pesticide. In various embodiments, the compound is a pesticidal compound.

[0047] In various embodiments, the compound of formula III(c) is represented by any one of the following structures: [Table 8] In various embodiments, the compound is a herbicidal compound. In various embodiments, the compound is for use in controlling undesirable plant growth. In various embodiments, the compound is a pesticide. In various embodiments, the compound is a pesticidal compound.

[0048] In various embodiments, the present invention is directed to a compound represented by any one of the structures shown in Table 1 above. In various embodiments, the compound is a herbicidal compound. In various embodiments, the compound is for use in controlling undesirable plant growth. In various embodiments, the compound is a pesticide. In various embodiments, the compound is a pesticidal compound.

[0049] In various embodiments, the present invention is directed to the use of a compound represented by any one of the structures shown in Table 1 or a pesticidal composition thereof in the control of pesticidal and / or herbicidal compounds and / or undesirable plant growth.

[0050] In various embodiments, ring A of the compounds of formula I, II(ad) and III(ac) is a 3-8 membered substituted or unsubstituted cycloalkyl. In various embodiments, ring A is absent. In various embodiments, ring A is an unsubstituted 3-8 membered cycloalkyl. In various embodiments, ring A is a substituted 3-8 membered cycloalkyl. In various embodiments, ring A is cyclopropyl. In various embodiments, ring A is cyclobutyl. In various embodiments, ring A is cyclopentyl. In various embodiments, ring A is cyclohexyl.

[0051] In various embodiments, ring B of the compounds of formula I, formula II(ad) and formula III(ab) is a 3-8 membered substituted or unsubstituted saturated or unsaturated carbocyclic ring. In various embodiments, ring B is absent. In various embodiments, ring B is a 3-8 membered substituted saturated ring. In various embodiments, ring B is a 3-8 membered substituted cycloalkyl. In various embodiments, ring B is a 3-8 membered unsubstituted saturated ring. In various embodiments, ring B is cyclohexyl. In various embodiments, ring B is a 3-8 membered unsubstituted cycloalkyl. In various embodiments, ring B is a 3-8 membered substituted unsaturated ring. In various embodiments, ring B is a 3-8 membered substituted cycloalkenyl. In various embodiments, ring B is a 3-8 membered unsubstituted unsaturated ring. In various embodiments, ring B is a 3-8 membered unsubstituted cycloalkenyl. In various embodiments, Ring B is a substituted or unsubstituted cyclohexenyl. In various embodiments, Ring B is a substituted or unsubstituted cyclopentyl. In various embodiments, Ring B is an amine-substituted cycloalkyl. In various embodiments, Ring B is an amine-substituted cycloalkenyl. In various embodiments, Ring B is a substituted or unsubstituted cyclohexenyl. In various embodiments, Ring B is a substituted or unsubstituted cyclopentyl. In various embodiments, Ring B is an amine-substituted cycloalkyl. In various embodiments, Ring B is an amine-substituted cycloalkenyl. In various embodiments, Ring B is an amine-substituted cycloalkenyl. 40 , R2′ and R3. In various embodiments, Ring B is substituted with R4, R 40 , R2' and R3, where at least one of R3 and R4 is an amine (e.g., NH2). In various embodiments, ring B is represented by formula (B): [ka] (wherein n is 0, 1 or 2). It is expressed as:

[0052] It is understood that the wavy line in Ring B represents the point of attachment of Ring B to the remainder of the molecule.

[0053] In various embodiments, Ring C of the compounds of Formula I, II(ad), and III(ac) is a 3-8 membered substituted or unsubstituted cycloalkyl. In various embodiments, Ring C is absent. In various embodiments, Ring C is unsubstituted cyclopropyl. In various embodiments, Ring C is substituted cyclopropyl. In various embodiments, Ring C is cyclobutyl, cyclopentyl, cyclohexyl; each of which represents a separate embodiment according to the present invention.

[0054] In some embodiments, at least one of the A ring, B ring, and C ring is present.

[0055] In some embodiments, C of formula (I) I is a substituted or unsubstituted carbon center. In some embodiments, C I is an unsubstituted carbon center and R is H. In some embodiments, C I is a substituted carbon center, and R is as defined below. I is the substituted carbon center, and R is R as defined below. 20 In some embodiments, C I is an sp carbon atom, sp depending on whether it is part of a triple bond, double bond or single bond, respectively. 2 Carbon atom or sp 3 In some embodiments, the C of formula I is I is an sp carbon atom; in that case, R is absent. I is C. In some embodiments, C I sp 2 In some embodiments, C I is CH. In some embodiments, C I is C(R 20 In some embodiments, CI is C-R1. In some embodiments, C I sp 3 In some embodiments, C I is CH2. In some embodiments, C I is CH(R 20 In some embodiments, C I is CH-R. In some embodiments, C I is C(R 20 )2.

[0056] In some embodiments, C of formula (I) II is a substituted or unsubstituted carbon center. In some embodiments, C II is an unsubstituted carbon center. In some embodiments, C II is a substituted carbon center. In some embodiments, C II is an sp carbon atom, sp depending on whether it is part of a triple bond, double bond or single bond, respectively. 2 Carbon atom or sp 3 In some embodiments, the C of formula I is II is an sp carbon atom. II is C. In some embodiments, C II sp 2 In some embodiments, C II is CH. In some embodiments, C II is C(R 20 In some embodiments, C II sp 3 In some embodiments, C II is CH2. In some embodiments, C II is CH(R 20 In some embodiments, C II is C(R 20 )2.

[0057] In some embodiments, C of formula (I) IIIis a substituted or unsubstituted carbon center. In some embodiments, C III is an unsubstituted carbon center. In some embodiments, C III is a substituted carbon center. In some embodiments, C III is an sp carbon atom, sp depending on whether it is part of a triple bond, double bond or single bond, respectively. 2 Carbon atom or sp 3 In some embodiments, the C of formula I is III is an sp carbon atom. III is C. In some embodiments, C III sp 2 In some embodiments, C III is CH. In some embodiments, C III is C(R 20 In some embodiments, C III sp 3 In some embodiments, C III is CH2. In some embodiments, C III is CH(R 20 In some embodiments, C III is C(R 20 )2.

[0058] In some embodiments, C of formula (I) IV is a substituted or unsubstituted carbon center. In some embodiments, C IV is an unsubstituted carbon center. In some embodiments, C IV is a substituted carbon center. In some embodiments, C IV is an sp carbon atom, sp depending on whether it is part of a triple bond, double bond or single bond, respectively. 2 Carbon atom or sp 3 In some embodiments, the C of formula I is IV is an sp carbon atom. IV is C. In some embodiments, C IV sp 2In some embodiments, C IV is CH. In some embodiments, C IV is C(R 20 In some embodiments, C IV sp 3 In some embodiments, C IV is CH2. In some embodiments, C IV is CH(R 20 In some embodiments, C IV is C(R 20 )2.

[0059] In some embodiments, R of formula (I) 20 is a halogen. In some embodiments, R 20 is F. In some embodiments, R 20 is Cl. In some embodiments, R 20 is Br. In some embodiments, R 20 is I. In some embodiments, R 20 is a C1-C5 straight or branched chain alkyl. In some embodiments, R 20 is methyl. In some embodiments, R 20 is ethyl. In some embodiments, R 20 is propyl. In some embodiments, R 20 is iso-propyl. In some embodiments, R 20 is butyl. In another embodiment, R 20 is not H. In some embodiments, R 20 is halogen or C1-C5 straight or branched alkyl. In some embodiments, R 20 is F or methyl.

[0060] In some embodiments, R of formula (I), formula II(ad) and / or formula III(ac) is C1-C5 linear or branched alkyl. In some embodiments, R is methyl. In some embodiments, R is ethyl. In some embodiments, R is propyl. In some embodiments, R is iso-propyl. In some embodiments, R is butyl. In some embodiments, R is C1-C5 linear or branched alkoxy. In another embodiment, R is methoxy. In some embodiments, R is phenyl. In some embodiments, R is aryl. In some embodiments, R is heteroaryl. In some embodiments, two geminal R substituents are joined together to form a 5- or 6-membered heterocyclic ring. In another embodiment, R is C1-C5 linear or branched alkyl, C1-C5 linear or branched alkoxy, phenyl, aryl, or heteroaryl. In another embodiment, R is not H.

[0061] In some embodiments, the C of the compound of formula (I) I …C II , C II …C III and C III …C IV are each independently a single bond or a double bond, where C I …C II , C II …C III and C III …C IV At least one of C is a double bond. I …C II is a single bond. In some embodiments, C I …C II is a double bond. In some embodiments, C II …C III is a single bond. In some embodiments, C II …C III is a double bond. In some embodiments, C III …C IV is a single bond. In some embodiments, C III …CIV is a double bond. In some embodiments, C I …C II , C II …C III and C III …C IV are each independently a single bond or a triple bond, where C I …C II , C II …C III and C III …C IV At least one of C is a triple bond. I …C II is a triple bond. In some embodiments, C I …C II is a triple bond, then R is absent. II …C III is a triple bond. In some embodiments, C III …C IV is a triple bond.

[0062] In some embodiments, R1 in the compounds of Formula I, II(ad) and / or III(ab) is H. In some embodiments, R1 is F. In some embodiments, R1 is Cl. In some embodiments, R1 is Br. In some embodiments, R1 is I. In some embodiments, R1 is a substituted or unsubstituted C1-C5 straight or branched chain alkyl. In some embodiments, R1 is methyl. In some embodiments, R1 is ethyl. In some embodiments, R1 is propyl. In some embodiments, R1 is iso-propyl. In some embodiments, R1 is t-Bu. In some embodiments, R1 is iso-butyl. In some embodiments, R1 is pentyl. In some embodiments, R1 is benzyl. In some embodiments, R1 is C1-C5 alkyl. In some embodiments, R1 is C2-C5 alkyl. In some embodiments, R1 is C3-C4 alkyl. In some embodiments, R1 is C4-C5 alkyl. In some embodiments, R1 is C5-C6 alkyl. In some embodiments, R1 is C6-C7 alkyl. In some embodiments, R1 is C7-C8 alkyl. In some embodiments, R1 is C8-C9 alkyl. In some embodiments, R1 is C9-C10 alkyl. In some embodiments, R1 is C1-C10 alkyl. In some embodiments, R1 is C1-C10 alkyl. In some embodiments, R1 is C1-C10 alkyl. In some embodiments, R1 is C1-C10 alkyl. In some embodiments, R1 is C1-C10 alkyl. In some embodiments, R1 is C1-C10 alkyl. In some embodiments, R1 is C2 ...1-C10 alkyl. In some embodiments, R1 is C1-C1 I …C IIis a triple bond, then R1 is absent. In some embodiments, R1 can 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), CF3, aryl, phenyl, heteroaryl (e.g., imidazole), C3-C8 cycloalkyl (e.g., cyclohexyl), CN, and NO2; each of which represents a separate embodiment according to the present invention.

[0063] In some embodiments, R2 of the compounds represented by Formula I, Formula II(ad) and / or Formula III(ac) is H. In some embodiments, R2 is F. In some embodiments, R2 is Cl. In some embodiments, R2 is Br. In some embodiments, R2 is I. In some embodiments, R2 is a substituted or unsubstituted C1-C5 straight or branched chain alkyl. In some embodiments, R2 is methyl. In some embodiments, R2 is ethyl. In some embodiments, R2 is propyl. In some embodiments, R2 is iso-propyl. In some embodiments, R2 is t-Bu. In some embodiments, R2 is iso-butyl. In some embodiments, R2 is pentyl. In some embodiments, R2 is a substituted or unsubstituted C2-C5 straight or branched chain alkenyl. In some embodiments, R2 is ethenyl. In some embodiments, R2 is CH=CH2. In some embodiments, R2 is a substituted or unsubstituted C2-C5 straight or branched chain alkynyl. In some embodiments, R2 is ethynyl. In some embodiments, R2 is CCH. In some embodiments, R2 can be further substituted with at least one substituent selected from F, Cl, Br, I, OH, SH, C1-C5 straight or branched chain alkyl (e.g., methyl, ethyl), C2-C5 straight or branched chain alkenyl, C2-C5 straight or branched chain alkynyl (e.g., CCH), C3-C8 cycloalkyl, straight, 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 of which represents a separate embodiment according to the present invention.

[0064] In some embodiments, R1 and R2 of Formula I, Formula II(ad) and / or Formula III(ab) are joined to form Ring B as defined above. In some embodiments, R1 and R2 are joined to form a substituted or unsubstituted saturated or unsaturated 3-8 membered carbocyclic ring. In some embodiments, R1 and R2 are joined to form a substituted saturated 3-8 membered carbocyclic ring. In some embodiments, R1 and R2 are joined to form a substituted unsaturated 3-8 membered carbocyclic ring. In some embodiments, R1 and R2 are joined to form an unsubstituted saturated 3-8 membered carbocyclic ring. In some embodiments, R1 and R2 are joined to form an unsubstituted unsaturated 3-8 membered carbocyclic ring. In some embodiments, R1 and R2 are joined to form a cyclohexyl. In some embodiments, R1 and R2 are joined to form a cyclohexenyl. In some embodiments, R1 and R2 are joined to form a cyclopentyl. In some embodiments, R1 and R2 are combined to form cyclopropyl. In some embodiments, R1 and R2 are combined to form cyclobutyl. In some embodiments, R1 and R2 are combined to form cycloheptyl.

[0065] In some embodiments, R2' in the compounds of Formula I, II(ad) and / or III(ac) is H. In some embodiments, R2' is F. In some embodiments, R2' is Cl. In some embodiments, R2' is Br. In some embodiments, R2' is I. In some embodiments, R2' is a substituted or unsubstituted C1-C5 straight or branched chain alkyl. In some embodiments, R2' is methyl. In some embodiments, R2' is ethyl. In some embodiments, R2' is propyl. In some embodiments, R2' is iso-propyl. In some embodiments, R2' is t-Bu. In some embodiments, R2' is iso-butyl. In some embodiments, R2' is pentyl. In some embodiments, R2' is a substituted or unsubstituted C2-C5 straight or branched chain alkenyl. In some embodiments, R2' is ethenyl. In some embodiments, R2' is CH=CH2. In some embodiments, R2' is a substituted or unsubstituted C2-C5 linear or branched alkynyl. In some embodiments, R2' is ethynyl. In some embodiments, R2' is CCH. In some embodiments, R2' can 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 of which represents a separate embodiment according to the present invention.

[0066] In some embodiments, R3 of the compounds represented by Formula I, Formula II(ad) and / or Formula III(ac) is H. In some embodiments, R3 is F. In some embodiments, R3 is Cl. In some embodiments, R3 is Br. In some embodiments, R3 is I. In some embodiments, R3 is OH. In some embodiments, R3 is SH. In some embodiments, R3 is NH2. In some embodiments, R3 is NHR. In some embodiments, R3 is N(R)2. In some embodiments, at least one of R3 and R4 is NH2, NH(R) or N(R)2. In some embodiments, at least one of R3 and R4 is NH2.

[0067] In some embodiments, R3 and R2' of the compounds of Formula I, II(ad) and / or III(ac) are joined to form Ring C, as defined above. In some embodiments, R3 and R2' are joined to form a substituted or unsubstituted 3-8 membered cycloalkyl. In some embodiments, R3 and R2' are joined to form an unsubstituted 3-8 membered cycloalkyl. In some embodiments, R3 and R2' are joined to form a cyclopropyl. In some embodiments, R3 and R2' are joined to form a cyclobutyl, cyclopentyl, cyclohexyl, or cycloheptyl; each of which represents a separate embodiment in accordance with the present invention. In some embodiments, R3 and R2' are joined to form a substituted 3-8 membered cycloalkyl.

[0068] In some embodiments, R4 of the compounds represented by Formula I, Formula II(ad) and / or Formula III(ac) is H. In some embodiments, R4 is F. In some embodiments, R4 is Cl. In some embodiments, R4 is Br. In some embodiments, R4 is I. In some embodiments, R4 is OH. In some embodiments, R4 is SH. In some embodiments, R4 is NH2. In some embodiments, R4 is NHR. In some embodiments, R4 is N(R)2. In some embodiments, at least one of R3 and R4 is NH2, NH(R) or N(R)2. In some embodiments, at least one of R3 and R4 is NH2.

[0069] In some embodiments, one of R3 and R4 is NH2 and the other is OH. In some embodiments, R3 is NH2 and R4 is OH. In some embodiments, R4 is NH2 and R3 is OH. In some embodiments, R3 is NH2 and R4 is OH; or R4 is NH2 and R3 is OH.

[0070] In some embodiments, R of the compound of Formula I, Formula II(ad) and / or Formula III(ac) is 40 is H. In some embodiments, R 40 is a C1-C5 straight or branched chain substituted or unsubstituted alkyl. In some embodiments, R 40 is a C1-C5 linear unsubstituted alkyl. In some embodiments, R 40 is a C1-C5 linear substituted alkyl. In some embodiments, R 40 is a C1-C5 branched substituted alkyl. In some embodiments, R 40 is a C1-C5 branched unsubstituted alkyl. In some embodiments, R 40 is methyl. In some embodiments, R 40 is ethyl. In some embodiments, R 40is propyl. In some embodiments, R 40 is iso-propyl. In some embodiments, R 40 is t-Bu. In some embodiments, R 40 is iso-butyl. In some embodiments, R 40 is pentyl. In some embodiments, R 40 may be further substituted with at least one substituent selected from F, Cl, Br, I, OH, SH, C1-C5 straight or branched chain alkyl (e.g., methyl, ethyl), C2-C5 straight or branched chain alkenyl, C2-C5 straight or branched chain alkynyl (e.g., CCH), C3-C8 cycloalkyl, straight, branched or cyclic alkoxy, COOH, COO(R), NH2, N(R), CF3, aryl, phenyl, heteroaryl (e.g., imidazole), C3-C8 cycloalkyl (e.g., cyclohexyl), CN, and NO2; each of which represents a separate embodiment in accordance with the present invention.

[0071] In some embodiments, R and R of the compound of Formula I, Formula II(ad) and / or Formula III(ac) are 40 are linked together to form ring A, as described above. In some embodiments, R and R 40 are joined together to form a substituted or unsubstituted 3-8 membered cycloalkyl. In some embodiments, R and R 40 are joined together to form an unsubstituted 3-8 membered cycloalkyl. In some embodiments, R and R 40 are joined together to form a substituted 3-8 membered cycloalkyl. In some embodiments, R and R 40 are linked together to form a cyclopropyl. In some embodiments, R and R 40 are linked together to form a cyclobutyl. In some embodiments, R and R 40 are joined together to form cyclopentyl. In some embodiments, R and R 40 are joined together to form cyclohexyl.

[0072] In some embodiments, R and R of the compounds of Formula I, II(ad) and / or III(ac) are 40 are joined together to form a substituted or unsubstituted 3-8 membered heterocyclic ring. In some embodiments, R and R 40 are joined to form a substituted or unsubstituted 3-8 membered cycloalkyl. In some embodiments, R and R 40 are joined to form an unsubstituted 3-8 membered cycloalkyl. In some embodiments, R and R 40 are linked to form a substituted 3-8 membered cycloalkyl. In some embodiments, R and R 40 In some embodiments, R and R 40 In some embodiments, R and R 40 are linked to form cyclopentyl. In some embodiments, R and R 40 combine to form cyclohexyl.

[0073] In some embodiments, R5 of the compounds represented by Formula I, II(ad) and / or III(ac) 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 alkylsulfone (e.g., SO2-CH2-cyclopropyl), substituted or unsubstituted aryl (e.g., phenyl), substituted or unsubstituted heteroaryl (e.g., pyridine (2, 3, and 4-pyridine); each of which represents a separate embodiment in accordance with the present invention. In some embodiments, R5 is H. In some embodiments, R5 is a C1-C5 straight or branched chain substituted or unsubstituted alkyl. In some embodiments, R5 is methyl, ethyl, iso-propyl, butyl, CH2-CCH, CH2-C(O)-OCH3; each of which represents a separate embodiment in accordance with the present invention. In some embodiments, R5 is a C2-C5 straight chain substituted or unsubstituted alkyl. In some embodiments, R5 is methyl, ethyl, iso-propyl, butyl, CH2-CCH, CH2-C(O)-OCH3; In some embodiments, R5 is a C2-C5 straight or branched substituted or unsubstituted alkynyl. In some embodiments, R5 is CCH. In some embodiments, R5 is CH2-CCH. In some embodiments, R5 is a C1-C5 straight or branched haloalkyl. In some embodiments, R5 is a substituted or unsubstituted alkylsulfone. In some embodiments, R5 is SO2-CH2-cyclopentyl. In some embodiments, R5 is SO2-CH2-cyclopropyl. In some embodiments, R5 is a substituted or unsubstituted aryl. In some embodiments, R5 is a substituted or unsubstituted heteroaryl. In some embodiments, R5 is pyridine.In some embodiments, R5 can be further substituted with at least one substituent selected from F, Cl, Br, I, OH, SH, C1-C5 straight or branched alkyl, C2-C5 straight or branched alkenyl, C2-C5 straight or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, straight, branched or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl, C3-C8 cycloalkyl, CN, and NO2; each of which represents a separate embodiment in accordance with the present invention.

[0074] In some embodiments, X1 in Formula I, Formula II(ad) and / or Formula III(ac) is O. In other embodiments, X1 is CH2. In other embodiments, X1 is NH. In other embodiments, X1 is NR 50 It is.

[0075] In some embodiments, R8 of Formula I, Formula II(ad) and / or Formula III(ac) is CH2. In other embodiments, R8 is CH2CH2. In other embodiments, R8 is CH2CH2CH2.

[0076] In some embodiments, p in Formula I, Formula II(ad) and / or Formula III(ac) is 1. In other embodiments, p is 2. In other embodiments, p is 3.

[0077] In some embodiments, R of Formula I, Formula II(ad) and / or Formula III(ac) 10 is H. In another embodiment, R 10 is H, CN, C1-C5 straight or branched chain alkyl, methyl, ethyl, C(O)R, C(O)(OCH3), or S(O)2R; each of which represents a separate embodiment according to the present invention. In another embodiment, R 10 is a C1-C5 straight or branched alkyl. 10 is CH3. In another embodiment, R 10is CH2CH3. In another embodiment, R 10 is CH2CH2CH3. In another embodiment, R 10 is CN. In another embodiment, R 10 is C(O)R. In another embodiment, R 10 is C(O)(OCH). In another embodiment, R 10 is S(O)R.

[0078] In some embodiments, R' of formula II(ad) and / or formula III(bc) is halogen. In some embodiments, R' is F. In some embodiments, R' is Cl. In some embodiments, R' is Br. In some embodiments, R' is I. In some embodiments, R' is a C1-C5 straight or branched chain alkyl. In some embodiments, R' is methyl. In some embodiments, R' is ethyl. In some embodiments, R' is propyl. In some embodiments, R' is iso-propyl. In some embodiments, R' is butyl. In some embodiments, R' is tert-butyl. In some embodiments, R' is pentyl. In some embodiments, R' is iso-pentyl.

[0079] In some embodiments, R'' of formula II(ad) and / or formula III(c) is halogen. In some embodiments, R'' is F. In some embodiments, R'' is Cl. In some embodiments, R'' is Br. In some embodiments, R'' is I. In some embodiments, R'' is a C1-C5 straight or branched chain alkyl. In some embodiments, R'' is methyl. In some embodiments, R'' is ethyl. In some embodiments, R'' is propyl. In some embodiments, R'' is iso-propyl. In some embodiments, R'' is butyl. In some embodiments, R'' is tert-butyl. In some embodiments, R'' is pentyl. In some embodiments, R'' is iso-pentyl.

[0080] In some embodiments, R''' of formula II(ad) and / or formula III(a) is halogen. In some embodiments, R''' is F. In some embodiments, R''' is Cl. In some embodiments, R''' is Br. In some embodiments, R''' is I. In some embodiments, R''' is a C1-C5 straight or branched chain alkyl. In some embodiments, R''' is methyl. In some embodiments, R''' is ethyl. In some embodiments, R''' is propyl. In some embodiments, R''' is iso-propyl. In some embodiments, R''' is butyl. In some embodiments, R''' is tert-butyl. In some embodiments, R''' is pentyl. In some embodiments, R''' is iso-pentyl.

[0081] In some embodiments, R of Formula I, Formula II(ad) and / or Formula III(ac) 50 is H. In some embodiments, R 50 is a C1-C5 straight or branched chain substituted or unsubstituted alkyl. 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 may be further substituted with at least one substituent selected from F, Cl, Br, I, OH, SH, C1-C5 straight or branched alkyl, C2-C5 straight or branched alkenyl, C2-C5 straight or branched alkynyl (e.g., CCH), C3-C8 cycloalkyl, straight, branched or cyclic alkoxy, COOH, COO(R), NH2, N(R)2, CF3, aryl, phenyl, heteroaryl, C3-C8 cycloalkyl, CN, and NO2; each of which represents a separate embodiment in accordance with the present invention.

[0082] In some embodiments, n of formula B is 0. In other embodiments, n is 1. In other embodiments, n is 2.

[0083] In various embodiments, the present invention is directed to any one of the compounds set forth in Table 1 herein above, agrochemical compositions and / or methods of use thereof in controlling undesirable plant growth.

[0084] In various embodiments, the present invention is directed to the use of any one of the compounds set forth in Table 2 herein above and / or agrochemical compositions thereof in controlling undesirable plant growth.

[0085] In structures presented in this invention where a carbon atom has less than four bonds, it is fully understood that H atoms are present to satisfy all of the carbon valences. In structures presented in this invention where a nitrogen atom has less than three bonds, it is fully understood that H atoms are present to satisfy all of the nitrogen valences.

[0086] In some embodiments, the present invention is directed to the compounds, agricultural chemical compositions and / or methods of use thereof listed herein above, wherein the compounds are agriculturally acceptable salts, zwitterions (inner salts), stereoisomers, optical isomers, tautomers, hydrates, N-oxides, reverse amide analogs, isotopic variants (deuterated analogs) or combinations thereof. In some embodiments, the compounds are herbicides. In some embodiments, the compounds are pesticides. In some embodiments, the compounds control undesirable plant growth.

[0087] In various embodiments, the compounds according to the present invention include substantially pure stereoisomers. By "substantially pure" is meant that the stereoisomer is 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 compounds contain a single stereoisomer with an enantiomeric excess (ee) purity of >80%, >85%, >90%, >91%, >92%, >93%, >94%, >95%, >96%, >97%, >98%, >99%, >99.5%; each of which represents a separate embodiment according to the present invention. In various embodiments, the compound contains a single stereoisomer in an enantiomeric ratio (er) of >80%, >85%, >90%, >91%, >92%, >93%, >94%, >95%, >96%, >97%, >98%, >99%, >99.5% purity; each of which represents a separate embodiment according to the invention. In various embodiments, the compound contains a single stereoisomer in a purity of greater than 80%, 85%, 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99%, 99.5% purity; each of which represents a separate embodiment according to the invention.

[0088] In various embodiments, the compound is a substantially pure single enantiomer. In various embodiments, the compound comprises a mixture of stereoisomers. In various embodiments, the compound comprises a mixture of enantiomers. In various embodiments, the compound is a racemate.

[0089] 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 of which represents a separate 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 110, described herein below. In various embodiments, the substantially pure stereoisomer has a purity of at least 80%, 85%, 90%, 95%, 97%, 98%, 99%; each of which represents a separate 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 a substantially pure SR stereoisomer.

[0090] As used herein, the term "alkyl," unless otherwise indicated, can be any straight or branched chain alkyl group containing up to about 30 carbons. In various embodiments, an alkyl comprises C1-C5 carbons. In some embodiments, an alkyl comprises C1-C6 carbons. In some embodiments, an alkyl comprises C1-C8 carbons. In some embodiments, an alkyl comprises C2-C5 carbons. In some embodiments, an alkyl comprises C2-C8 carbons. In some embodiments, an alkyl comprises C1-C 10 In some embodiments, alkyl is C-C 12 In some embodiments, alkyl is C-C 20In some embodiments, the branched alkyl is an alkyl substituted with an alkyl side chain of 1 to 5 carbons. In various embodiments, the alkyl group can be unsubstituted. In some embodiments, the alkyl group can be substituted with halogen, haloalkyl, hydroxyl, alkoxy, carbonyl, amido, alkylamido, dialkylamido, cyano, nitro, CO2H, amino, alkylamino, dialkylamino, carboxyl, thio, thioalkyl, C1-C5 straight or branched chain 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.

[0091] An alkyl group can be a single substituent or can be a component of a larger substituent such as alkoxy, alkoxyalkyl, haloalkyl, arylalkyl, alkylamino, dialkylamino, alkylamide, alkylurea, etc. Preferred alkyl groups are methyl, ethyl and propyl, thus 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), etc.

[0092] As used herein, the term "alkenyl" can be any straight or branched chain alkenyl group containing up to about 30 carbons and at least one carbon-carbon double bond, as defined herein above for the term "alkyl." Thus, the term "alkenyl" as defined herein also encompasses alkadienes, alkatrienes, alkatetraenes, and the like. In some embodiments, an alkenyl group contains one carbon-carbon double bond. In some embodiments, an alkenyl group contains 2, 3, 4, 5, 6, 7, or 8 carbon-carbon double bonds; each of which represents a separate 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 isobutylenyl), pentene (i.e., 1-pentenyl, cis-2-pentenyl, and trans-2-pentenyl), hexene (e.g., 1-hexenyl, (E)-2-hexenyl, (Z)-2-hexenyl, (E)-3-hexenyl, (Z)-3-hexenyl, 2-methyl-1-pentene, and the like), all of which may be substituted as defined herein above for the term "alkyl."

[0093] As used herein, the term "alkynyl" can be any straight or branched chain alkynyl group containing up to about 30 carbons 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 alkadienes, alkatoiynes, alkatetraynes, and the like. In some embodiments, the alkynyl group contains one carbon-carbon triple bond. In some embodiments, the alkynyl group contains 2, 3, 4, 5, 6, 7, or 8 carbon-carbon triple bonds; each of which represents a separate embodiment according to the present invention. Non-limiting examples of alkynyl groups include acetylenyl, propynyl, butynyl (i.e., 1-butynyl, 2-butynyl, and isobutynyl), pentynyl (i.e., 1-pentynyl, 2-pentynyl), hexynyl (e.g., 1-hexynyl, 2-hexynyl, 3-hexynyl, etc.), all of which may be substituted as defined herein above for the term "alkyl."

[0094] As used herein, the term "aryl" refers to any aromatic ring that is directly attached to another group and can be either substituted or unsubstituted. An aryl group can also be a single substituent or it can be a component of a larger substituent such as arylalkyl, arylamino, arylamide, etc. Exemplary aryl groups include, but are not limited to, phenyl, tolyl, xylyl, furanyl, naphthyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thiazolyl, oxazolyl, isoxazolyl, pyrazolyl, imidazolyl, thiophen-yl, pyrrolyl, indolyl, phenylmethyl, phenylethyl, phenylamino, phenylamido, 3-methyl-4H-1,2,4-triazolyl, 5-methyl-1,2,4-oxadiazolyl, and the like. Substituents include, but are not limited to, F, Cl, Br, I, C1-C5 straight or branched alkyl, C1-C5 straight or branched haloalkyl, C1-C5 straight or branched alkoxy, C1-C5 straight 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.

[0095] As used herein, "heteroaryl" can be any ring, including, but not limited to, pyridinyl, (2-, 3-, and 4-pyridinyl), quinolyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, tetrazinyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, imidazolyl, 1-methylimidazole, pyrazolyl, pyrrolyl, furanyl, thiophen-yl, quinolinyl, isoquinolinyl, 2,3-dihydroindenyl, indenyl, tetrahydronaphthyl, 3,4-dihydro-2H-benzo[b][1,4]dioxepin, benzodioxolyl, benzo[d][1, 3]dioxole, 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-indol-3-one, purinyl, benzoxazolyl, 1,3-benzoxazolyl, benzisoxazolyl, benzothiazolyl, 1,3-benzothiazole, 4,5,6,7-tetrahydro-1,3-benz[d]imidazolyl, benzothiazole, quinazolinyl, quinoxalinyl, 1,2,3,4-tetrahydroquinoxaline, 1-(pyridin-1(2H)-yl)ethanone, cinnolinyl, phthalazinyl, quinolinyl, isoquinolinyl, acridinyl, benzofuranyl, 1-benzofuran, isobenzofuranyl, benzofuran-2(3H)-one, benzothiophenyl, benzoxadiazole, benzo[c][1,2,5]oxadiazolyl, benzo[c]thiophenyl, benzodioxolyl, thiadiazolyl, [1,3]oxazolo[4,5 -b]pyridine, oxadiazolyl, imidazo[2,1-b][1,3]thiazole, 4H,5H,6H-cyclopenta[d][1,3]thiazole, iazole, 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]pyrimidin-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]pyrazin-3(4H)-one, 4H-thieno[3,2-b]pyridine rol, quinoxalin-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, methyloxazolidin-2-one, and the like; each of which represents a separate embodiment of the present invention.

[0096] As used herein, the term "alkoxy" refers to an ether group substituted with an alkyl group as defined above. Alkoxy refers to both straight and branched chain alkoxy groups. Non-limiting examples of alkoxy groups are methoxy, ethoxy, propoxy, iso-propoxy, tert-butoxy.

[0097] A "haloalkyl" group refers, in some embodiments, to an alkyl group as defined above that 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, 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.

[0098] A "halophenyl" group, in some embodiments, refers to a phenyl substituent that is substituted with one or more halogen atoms, such as F, Cl, Br, or I. In one embodiment, the halophenyl is 4-chlorophenyl.

[0099] An "alkoxyalkyl" group refers, in some embodiments, to an alkyl group as defined above that is substituted with an alkoxy group as defined above, e.g., methoxy, ethoxy, propoxy, i-propoxy, t-butoxy, etc. Non-limiting examples of alkoxyalkyl groups are -CH2-O-CH3, -CH2-O-CH(CH3), -CH2-OC(CH3), -CH2-CH2-O-CH3, -CH2-CH2-O-CH(CH3), -CH2-CH2-OC(CH3).

[0100] A "cycloalkyl" or "carbocyclic" group, in various embodiments, refers to a ring structure that includes carbon atoms as ring atoms, and can be either saturated or unsaturated, substituted or unsubstituted, single or fused. In some embodiments, a cycloalkyl is a 3- to 10-membered ring. In some embodiments, a cycloalkyl is a 3- to 12-membered ring. In some embodiments, a cycloalkyl is a 6-membered ring. In some embodiments, a cycloalkyl is a 5- to 7-membered ring. In some embodiments, a cycloalkyl is a 3- to 8-membered ring. In some embodiments, the cycloalkyl group can be unsubstituted or substituted with halogen, alkyl, haloalkyl, hydroxyl, alkoxy, carbonyl, amido, alkylamido, dialkylamido, cyano, nitro, CO2H, amino, alkylamino, dialkylamino, carboxyl, thio, thioalkyl, C1-C5 straight or branched chain 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 can be fused to another saturated or unsaturated cycloalkyl or heterocyclic 3-8 membered ring. In some embodiments, the cycloalkyl ring is a saturated ring. In some embodiments, the cycloalkyl ring is an unsaturated ring. Non-limiting examples of cycloalkyl groups include cyclohexyl, cyclohexenyl, cyclopropyl, cyclopropenyl, cyclopentyl, cyclopentenyl, cyclobutyl, cyclobutenyl, cyclooctyl, cyclooctadienyl (COD), cyclooctaenyl (COE), and the like.

[0101] A "heterocycle" group or a "heterocyclic" group, in various embodiments, refers to a ring structure that, in addition to carbon atoms, contains sulfur, oxygen, nitrogen, or any combination thereof as part of the ring. An "aromatic heterocycle", in various embodiments, refers to an aromatic ring structure that, in addition to carbon atoms, contains sulfur, oxygen, nitrogen, selenium, or any combination thereof as part of the ring. In some embodiments, the heterocycle or aromatic heterocycle is a 3- to 10-membered ring. In some embodiments, the heterocycle or aromatic heterocycle is a 3- to 12-membered ring. In some embodiments, the heterocycle or aromatic heterocycle is a 6-membered ring. In some embodiments, the heterocycle or aromatic heterocycle is a 5- to 7-membered ring. In some embodiments, the heterocycle or aromatic heterocycle is a 3- to 8-membered ring. In some embodiments, the heterocyclic group or aromatic heterocycle can be unsubstituted or substituted with halogen, alkyl, haloalkyl, hydroxyl, alkoxy, carbonyl, amido, alkylamido, dialkylamido, cyano, nitro, CO2H, amino, alkylamino, dialkylamino, carboxyl, thiol, thioalkyl, C1-C5 straight or branched chain 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 can be fused to another saturated or unsaturated cycloalkyl or heterocyclic 3-8 membered ring. In some embodiments, the heterocyclic ring is a saturated ring. In some embodiments, the heterocyclic ring is an unsaturated ring. In some embodiments, the heterocyclic ring is an aliphatic ring.Non-limiting examples of heterocyclic rings or aromatic heterocyclic ring 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, oxazolidin-2-one, methyloxazolidin-2-one, or indole; each of which represents a separate embodiment according to the present invention.

[0102] In various embodiments, the present invention provides a compound of the present invention or a pesticidally acceptable salt, zwitterion (inner salt), stereoisomer, optical isomer, tautomer, hydrate, N-oxide, reverse amide analog, isotopic variant (e.g., deuterated analog), or combination thereof. In various embodiments, the present invention provides a single stereoisomer of a compound of the present invention. In some embodiments, the present invention provides an optical isomer of a compound of the present invention. In some embodiments, the present invention provides a pesticidally acceptable salt of a compound of the present invention. In some embodiments, the present invention provides a tautomer of a compound of the present invention. In some embodiments, the present invention provides a hydrate of a compound of the present invention. In some embodiments, the present invention provides an N-oxide of a compound of the present invention. In some embodiments, the present invention provides a reverse amide analog of a compound of the present invention. In some embodiments, the present invention provides an isotopic variant of a compound of the present invention, including, but not limited to, a deuterated analog. In some embodiments, the present invention provides a polymorph of a compound of the present invention. In some embodiments, the present invention provides a crystal of a compound of the present invention. In some embodiments, the present invention provides pesticide compositions, wherein the pesticide compositions comprise a compound of the present invention described herein, or in some embodiments, any combination of stereoisomers, optical isomers, pesticidally acceptable salts, zwitterions (inner salts), tautomers, hydrates, N-oxides, isotopic variants (deuterated analogs), polymorphs, or crystals of a compound of the present invention.

[0103] In various embodiments, the term "isomer" encompasses stereoisomers, including, but not limited to, 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.

[0104] Certain compounds of the present invention may exist in specific geometric or stereoisomeric forms. The present invention contemplates that all such compounds, including cis- and trans-isomers, R- and S-enantiomers, diastereomers, racemic mixtures thereof, and other mixtures thereof, are within the scope of the present invention. Additional asymmetric carbon atoms may be present in substituents such as alkyl groups. All such isomers and mixtures thereof are intended to be encompassed herein.

[0105] 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 appreciate that the compounds of the present invention may contain at least one chiral center.Therefore, the compounds used in the methods of the present invention can exist in optically active or racemic form and can be isolated in optically active or racemic form. Compounds according to the present invention may further exist as stereoisomers which may be optically active isomers (e.g., enantiomers such as (R) or (S)), enantiomer-enriched mixtures, racemic mixtures, or as single diastereomers, diastereomeric mixtures, or any other stereoisomers, including, but not limited to, (R)(R), (R)(S), (S)(S), (S)(R), (R)(R)(R), (R)(R)(S), (R)(S)(R), (S)(R)(S), (S)(R)(S), or (S)(S)(S) stereoisomers. Some compounds may furthermore exhibit polymorphism. It is to be understood that the present invention encompasses any racemic, optically active, polymorphic or stereoisomeric form, or mixtures thereof, which forms possess properties useful for controlling various undesirable plant growth as described herein.

[0106] It is well known in the art how to prepare optically active forms (for example, by resolution of racemic forms by recrystallization techniques, by synthesis from optically active starting materials, by chiral synthesis, or by chromatographic separation using chiral stationary phases).

[0107] The compounds of the present invention can also be in the form of racemic mixtures containing substantially equal amounts of stereoisomers. In some embodiments, the compounds of the present invention can be prepared or otherwise isolated using known procedures to obtain a stereoisomer that is substantially free of its corresponding stereoisomer (i.e., substantially pure). By "substantially pure" it is intended that the stereoisomer is at least about 95% pure, more preferably at least about 98% pure, and most preferably at least about 99% pure. In various embodiments, the compounds according to the present invention comprise substantially pure stereoisomers. In some embodiments, the substantially pure stereoisomer is at least 70%, 75%, 80%, 85%, 90%, 93%, 95%, 97%, 98%, 99%, 99.5% pure; each of which represents a separate embodiment according to the present invention.

[0108] In various embodiments, the compound comprises a single stereoisomer in an enantiomeric excess (ee) purity of >80%, >85%, >90%, >91%, >92%, >93%, >94%, >95%, >96%, >97%, >98%, >99%, >99.5%, each of which represents a separate embodiment according to the present invention. In various embodiments, the compound comprises a single stereoisomer in an enantiomeric ratio (er) purity of >80%, >85%, >90%, >91%, >92%, >93%, >94%, >95%, >96%, >97%, >98%, >99%, >99.5%, each of which represents a separate embodiment according to the present invention. In various embodiments, the compound comprises a single stereoisomer at greater than 80%, 85%, 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99%, 99.5% purity; each of which represents a separate embodiment according to the present invention. In some embodiments, the compound is compound 110.

[0109] In various embodiments, the compound is a substantially pure single enantiomer. In various embodiments, the compound comprises a mixture of enantiomers. In various embodiments, the compound is a racemate.

[0110] 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 of which represents a separate 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 has a purity of at least 80%, 85%, 90%, 95%, 97%, 98%, 99%; each of which represents a separate 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 a substantially pure SR stereoisomer.

[0111] The compounds of the present invention may further be in the form of hydrates, which means that the compounds further contain stoichiometric or non-stoichiometric amounts of water bound by non-covalent intermolecular forces.

[0112] As used herein, when certain chemical functional groups (e.g., alkyl or aryl) are said to be "substituted," it is defined herein that one or more substitutions are possible.

[0113] The compounds of the present invention can exist in one or more possible tautomeric forms, 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 further enol and keto tautomers and / or isomers) are encompassed by this specification. For example, but not limited to, the following tautomers are included: Tautomerism of the imidazole ring: [ka] Tautomerism of the pyrazolone ring: [ka] The present invention includes "pesticidally acceptable salts" of the compounds of the present invention, which can be prepared by reacting the compounds of the present invention with an acid or base. Certain compounds, particularly those with acidic or basic groups, can also be in the form of salts, preferably in the form of pesticidally acceptable salts. The term "pesticidally acceptable salts" refers to those salts that retain the pesticidal effectiveness and properties of the free base or free acid, which are not pesticidal or otherwise undesirable. Such salts are formed with inorganic acids (e.g., hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid, etc.) and organic acids (e.g., 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, N-acetylcysteine, etc.). Other salts are known to those skilled in the art and can be readily adapted for use in accordance with the present invention.

[0114] Suitable agriculturally 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 amines are bisulfate, borate, bromide, chloride, hemisulfate, hydrobromide, hydrochloride, 2-hydroxyethylsulfonate (hydroxyethanesulfonate), iodate, iodide, isothiocyanate, nitrate, persulfate, phosphate, sulfate, sulfamate, sulfanilate, sulfonic acid (alkylsulfonate, arylsulfonate, halogen-substituted alkylsulfonate, halogen-substituted arylsulfonate), sulfonate and thiocyanate.

[0115] In various embodiments, exemplary organic salts of amines can be selected from the aliphatic, cycloaliphatic, aromatic, araliphatic, heterocyclic, carboxylic, and sulfonic classes of organic acids.Examples thereof are acetate, aspartate, ascorbate, adipate, anthranilate, alginate, alkanecarboxylate, substituted alkanecarboxylate, alginate, benzenesulfonate, benzoate, bisulfate, butyrate, bicarbonate, bitartrate, citrate, camphorate, camphorsulfonate, cyclohexylsulfamate, cyclopentanepropionate, calcium edetate, camsylate, carbonate, clavulanate, cinnamate, dicarboxylate, digluconate, dodecylsulfonate, dihydrochloride, Decanoate, enanthate, ethanesulfonate, edetic acid, edisylate, estrus, esylate, fumarate, formate, fluoride, galacturonate, gluconate, glutamate, glycolate, gluconate, glucoheptanoate, glycerophosphate, gluceptate, glycolylarsanilate, glutarate, glutamate, heptanoate, hexanoate, hydroxymaleate, hydroxycarboxylic acid, hexylresorcinate, hydroxybenzoate, hydroxynaphthoate, fluoride Salt, lactate, lactobionate, laurate, malate, maleate, methylenebis(β-oxynaphthoate), malonate, mandelate, mesylate, methanesulfonate, methyl bromide, methyl nitrate, methylsulfonate, monopotassium maleate, mucate, monocarboxylate, naphthalenesulfonate, 2-naphthalenesulfonate, nicotinate, nitrate, napsylate, N-methylglucamine, oxalate, octanoate, oleate, pamoate, phenylacetate, picrate, phenylbenzoate, picrate The salts are valate, propionate, phthalate, phenylacetate, pectinate, phenylpropionate, palmitate, pantothenate, polygalacturonate, pyruvate, quinate, salicylate, succinate, stearate, sulfanilate, subacetate, tartrate, theophylline acetate, p-toluenesulfonate (tosylate), trifluoroacetate, terephthalate, tannate, theoclate, trihaloacetate, triethiodide, tricarboxylate, undecanoate and valerate.

[0116] In various embodiments, examples of inorganic salts of carboxylic acids or hydroxyls may be selected from ammonium, alkali metals (e.g., lithium, sodium, potassium, cesium), alkaline earth metals (e.g., calcium, magnesium, aluminum), zinc, barium, and quaternary ammonium.

[0117] In some embodiments, examples of organic salts of carboxylic acids or hydroxyls may be selected from arginine, organic amines (which include aliphatic organic amines, cycloaliphatic organic amines, aromatic organic amines), benzathine, t-butylamine, benethamine (N-benzylphenethylamine), dicyclohexylamine, dimethylamine, diethanolamine, ethanolamine, ethylenediamine, hydrabamine, imidazole, lysine, methylamine, meglamine, N-methyl-D-glucamine, N,N'-dibenzylethylenediamine, nicotinamide, organic amines, ornithine, pyridine, picoline, piperazine, procaine, tris(hydroxymethyl)methylamine, triethylamine, triethanolamine, trimethylamine, tromethamine, and urea.

[0118] In various embodiments, the salts can be formed by conventional means, for example, by reacting the free base or free acid form of the product with one or more equivalents of the appropriate acid or base in a solvent or medium in which the salt is insoluble, or in a solvent such as water which is removed under reduced pressure or by lyophilization, or by exchanging ions of an existing salt with other ions or with a suitable ion exchange resin.

[0119] Pesticide Composition Another aspect of the present invention relates to an agrochemical composition comprising a pesticidally acceptable carrier or diluent and a compound according to an aspect of the present invention. The agrochemical composition may contain one or more of the above-identified compounds of the present invention. Typically, the agrochemical composition of the present invention contains a compound of the present invention or its pesticidally acceptable salt, zwitterion (inner salt), and a pesticidally acceptable carrier or diluent. The term "pesticidally acceptable carrier" refers to any suitable adjuvant, carrier, excipient, or stabilizer, and may be in solid or liquid form, such as a spray, aerosol, powder, solution, suspension, or emulsion.

[0120] Although the compounds according to the invention can be used as pesticides or herbicides in unmodified form, they are generally formulated into compositions in various ways using formulation adjuvants such as carriers, solvents and surface active substances.The formulations can be in various physical forms, such as dispersible powders, gels, wettable powders, water-dispersible granules, water-dispersible tablets, effervescent pellets, emulsifiable concentrates, microemulsifiable concentrates, oil-in-water emulsions, oily flowables, aqueous dispersions, oily dispersions, suspoemulsions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrates (using water or water-miscible organic solvents as carriers), impregnated polymer films or other forms known in the art.Such formulations can be used as is or can be diluted before use.Dilution can be carried out, for example, with water, liquid fertilizers, micronutrients, biological organisms, oils or solvents.

[0121] Typically, the compositions contain about 0.01-99%, preferably about 20-75%, of the active compound together with the adjuvant, carrier and / or excipient. While individual needs may vary, determination of optimal ranges of effective amounts of each component is within the skill of one of ordinary skill in the art.

[0122] The formulations can be prepared, for example, by mixing the active ingredient with formulation adjuvants to obtain compositions in the form of finely divided solids, granules, solutions, dispersions or emulsions. The active ingredient can also be formulated with other adjuvants, such as finely divided solids, mineral oils, oils of vegetable or animal origin, modified oils of vegetable or animal origin, organic solvents, water, surface-active substances or combinations thereof.

[0123] The active ingredient can also be contained in ultrafine microcapsules. Microcapsules contain the active ingredient in a porous carrier. This allows the active ingredient to be released in controlled amounts into the environment (e.g., sustained release). Microcapsules usually 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 a monolithic solid, in the form of fine particles in a solid or liquid dispersion medium, or in the form of a suitable solution. The encapsulating membrane can include, for example, natural or synthetic rubbers, cellulose, styrene / butadiene copolymers, polyacrylonitrile, polyacrylates, polyesters, polyamides, polyureas, polyurethanes or chemically modified polymers and starch xanthates, or other polymers known to those skilled in the art. Alternatively, ultrafine microcapsules can be formed such that the active ingredient is contained in the form of finely divided particles in a solid matrix of a base material, but the microcapsules themselves are not encapsulated.

[0124] Formulation adjuvants suitable for preparing the compositions according to the invention are known per se. The following can be used as liquid carriers: water, toluene, xylene, petroleum ether, vegetable oils, acetone, methyl ethyl ketone, cyclohexanone, acid anhydrides, acetonitrile, acetophenone, amyl acetate, 2-butanone, butylene carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetates, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietic acid, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, dimethylformamide (DMF), dimethylsulfoxide (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, octadecane Canic acid, octylamine acetate, oleic acid, 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, methyl-2-pyrrolidone, etc.

[0125] Suitable solid carriers are, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, diatomaceous earth, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, ground walnut shells, lignin and similar materials.

[0126]

[0135] Many types of surface-active substances can be advantageously used in both solid and liquid formulations, especially in those which can be diluted with a carrier before use. Surface-active substances can be anionic, cationic, nonionic or polymeric and they can be used as emulsifying agents, wetting agents or suspending agents or for other purposes. Typical surface-active substances include, for example, salts of alkyl sulfates, such as diethanolammonium lauryl sulfate, salts of alkylaryl sulfonates, such as calcium dodecylbenzene sulfonate, alkylphenol / alkylene oxide adducts, such as nonylphenol ethoxylate, alcohol / alkylene oxide adducts, such as tridecyl alcohol ethoxylate, soaps, such as sodium stearate, salts of alkylnaphthalene sulfonates, such as sodium dibutylnaphthalene sulfonate, dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl) sulfosuccinate, sorbitol esters, such as sorbitol oleate, quaternary amines, such as lauryl trimethylammonium 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, and further substances known in the art.

[0127] Further adjuvants that may be used in the pesticide or herbicide formulations include crystallization inhibitors, viscosity modifiers, suspending agents, dyes, antioxidants, foaming agents, light absorbers, mixing aids, defoamers, complexing agents, neutralizing or pH adjusting substances and buffers, corrosion inhibitors, flavorings, wetting agents, uptake enhancers, micronutrients, plasticizers, flow enhancers, lubricants, dispersants, thickeners, antifreeze agents, fungicides, and liquid and solid fertilizers.

[0128] The composition according to the invention may contain an additive comprising an oil of vegetable or animal origin, a mineral oil, an alkyl ester of such an oil or a mixture of such an oil and an oil derivative. The amount of oil additive in the composition according to the invention is generally 0.01-10% based on the mixture to be applied. For example, after the spray mixture is prepared, the oil additive can be added to the spray tank in the desired concentration. Preferred oil additives include mineral oils or oils of vegetable origin, such as rapeseed oil, olive oil or sunflower oil, emulsified vegetable oils, alkyl esters of oils of vegetable origin, such as methyl derivatives, or oils of animal origin, such as fish oil or beef tallow. Preferred oil additives include C8-C 22 Alkyl esters of fatty acids, especially C 12 -C 18 Methyl derivatives of fatty acids, such as the methyl esters of lauric acid, palmitic acid, and oleic acid (methyl laurate, methyl palmitate, and methyl oleate, respectively). Other oil derivatives are described, for example, in the Compendium of Herbicide Adjuvants, 10 th Edition, Southern Illinois University, 2010, are known to those skilled in the art.

[0129] A pesticide or herbicide composition generally contains 0.1 to 99% by weight (particularly 0.1 to 95% by weight) of the compound according to the invention and 1 to 99.9% by weight of formulation adjuvants (which preferably contain 0 to 25% by weight of surface-active substances). A composition according to the invention generally contains 0.1 to 99% by weight (particularly 0.1 to 95% by weight) of the compound according to the invention and 1 to 99.9% by weight of formulation adjuvants (which preferably contain 0 to 25% by weight of surface-active substances). Commercial products can be preferably formulated as concentrates, but end users usually use dilute formulations.

[0130] The application rates vary within wide limits and depend on the nature of the soil, the application method, the crop plant, the pests to be controlled, the prevailing climatic conditions, as well as on other factors governed by the application method, application time and the target crop. As a general guideline, the compounds may be applied at application rates of 1 to 2000 L / ha, in particular 10 to 1000 L / ha. Preferred formulations may have the following composition (wt%):

[0131] emulsion: * Active ingredients: 1-95%, preferably 60-90%; * Surfactant: 1-30%, preferably 5-20%; * Liquid carrier: 1-80%, preferably 1-35%; Powder: * Active ingredient: 0.1-10%, preferably 0.1-5%; * Solid carrier: 90-99.9%, preferably 99-99.9%; Suspension formulations: * Active ingredients: 5-75%, preferably 10-50%; * Water: 24-94%, preferably 30-88%; * Surfactant: 1-40%, preferably 2-30%; Wettable powder: * Active ingredient: 0.5-90%, preferably 1-80%; * Surfactant: 0.5-20%, preferably 1-15%; * Solid carrier: 5-95%, preferably 15-90%; Granules: * Active ingredient: 0.1-30%, preferably 0.1-15%; *Solid carrier: 70-99.5%, preferably 85-97%.

[0132] When the compounds or pesticide compositions of the present invention are applied to control undesirable plant growth, the pesticide compositions may also contain or be applied in conjunction with other pesticides or treatment regimes now known or hereafter developed for controlling the growth of various types of plants.

[0133] Thus, the composition of the present invention can further comprise at least one additional pesticide, including but not limited to a herbicide. For example, the compound according to the present invention can also be used in combination with other pesticides, herbicides or plant growth regulators. In a preferred embodiment, the additional pesticide is a herbicide and / or a herbicide safener.

[0134] Examples of herbicides which may be used in combination with the compounds of the present invention include, but are not limited to, acetochlor, acifluorfen (including acifluorfen-sodium), aclonifen, alachlor, alloxydim, ametryn, amicarbazone, amidosulfuron, aminocyclopyrachlor, aminopyralid, amitrole, asulam, atrazine, bensulfuron (including bensulfuron-methyl), bentazon, bicyclopyrone, vilanaphos, bifenox, bispyribac-sodium, Bixthrozone, bromacil, bromoxynil, butachlor, butafenacil, cafenstrole, carfentrazone (including carfentrazone-ethyl), cloransulam (including cloransulam-methyl), chlorimuron (including chlorimuron-ethyl), chlorotoluron, cinosulfuron, chlorsulfuron, cinmethylin, clasifos, clethodim, clodinafop (including clodinafop-propargyl), clomazone, clopyralid, cyclopyranyl, cyclopyrimorate, cyclosulfamuron, cyhalofop (including its cyhalofop-butyl), 2,4-D (including its choline salt and 2-ethylhexyl ester), 2,4-DB, dymron, desmedipham, dicamba (including its aluminum, aminopropyl, bisaminopropylmethyl, choline, dichloroprop, diglycolamine, dimethylamine, dimethylammonium, potassium and sodium salts), diclofop-methyl, diclosulam, diflufenican, difenzoquat, diflufenican, diflufenzopyr, dimethachlor, dimethenamid-P, diquat-dib romide, diuron, esprocarb, ethalfluralin, ethofumesate, fenoxaprop (including fenoxaprop-P-ethyl), fenoxasulfone, fenquinotrione, fentrazamide, flazasulfuron, florasulam, florpyrauxifen, fluazifop (including fluazifop-P-butyl), flucarbazone (including flucarbazone-sodium), flufenacet, flumetralin, flumetsulam, flumioxazin, flupyrsulfuron (including flupyrsulfuron-methyl-sodium),Fluroxypyr (including fluroxypyr-meptyl), fluthiacet-methyl, fomesafen, foramsulfuron, glufosinate (including its ammonium salts), glyphosate (including its diammonium, isopropylammonium and potassium salts), halaxifen (including halaxifen-methyl), halosulfuron-methyl, haloxyfop (including haloxyfop-methyl), hexazinone, hydantocidin, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, indaziflam, iodine, iodine-methyl ... Dosulfuron (including iodosulfuron-methyl-sodium), iofensulfuron, iofensulfuron-sodium, ioxynil, ipfencarbazone, isoproturon, isoxaben, isoxaflutole, lactofen, lancotrione, linuron, MCPA, MCPB, mecoprop-P, mefenacet, mesosulfuron, mesosulfuron-methyl, mesotrione, metamitron, metazachlor, methiozoline, metobromuron, metolachlor, metosulam, methoxuron, metribuzin, metsulfuron, molinate , napropamide, nicosulfuron, norflurazon, orthosulfamuron, oxadiargyl, oxadiazon, oxasulfuron, oxyfluorfen, paraquat dichloride, pendimethalin, penoxsulam, phenmedipham, picloram, picolinafen, pinoxaden, pretilachlor, primisulfuron-methyl, prodiamine, prometryn, propachlor, propanil, propaquizafop, propham, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen (pyraflufen) quizalofop (including quizalofop-p-ethyl and quizalofop-p-tefuryl), rimsulfuron, saflufenacil, sethoxydim, simazine, S-metolachlor, sulcotrione, sulfentrazone, sulfosulfuron, tebuthiuron, tefuryltrione, tembotrione,Terbuthylazine, terbutryn, thiencarbazone, thifensulfuron, thiaphenacyl, tolpyralate, topramezone, tralkoxydim, triafamone, triallate, triasulfuron, tribenuron (including triaberonuron-methyl), triclopyr, trifloxysulfuron (including trifloxysulfuron-sodium), trifludimoxazine, trifluralin, triflusulfuron, tritosulfuron, 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)-2-pyridyl]i Midazolidin-2-one, 4-hydroxy-1,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one, 5-ethoxy-4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one, 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one, 4-hydroxy-1,5-dimethyl-3-[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]imidazolidin-2-one, (4R)1- (5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2-one, 3-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]bicyclo[3.2.1]octane-2,4-dione, 2-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]-5-methyl-cyclohexane-1,3-dione, 2-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbo 2-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]-5,5-dimethyl-cyclohexane-1,3-dione, 6-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]-2,2,4,4-tetramethyl-cyclohexane-1,3,5-trione, 2-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]-5-ethyl-cyclohexane-1,3-dione,2-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]-4,4,6,6-tetramethyl-cyclohexane-1,3-dione, 2-[6-cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxo-pyridazine-4-carbonyl]-5-methyl-cyclohexane-1,3-dione, 3-[6-cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxo-pyridazine-4-carbonyl]bicyclo[3.2.1]octane-2,4-dione, 2-[6-cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxo-pyridazine-4-carbonyl]-5,5-dimethyl-cyclohexane-1,3-dione, 6-[6-cyclopropyl propyl-2-(3,4-dimethoxyphenyl)-3-oxo-pyridazine-4-carbonyl]-2,2,4,4-tetramethyl-cyclohexane-1,3,5-trione, 2-[6-cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxo-pyridazine-4-carbonyl]cyclohexane-1,3-dione, 4-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]-2,2,6,6-tetramethyl-tetrahydropyran-3,5-dione, and I+4-[6-cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxo-pyridazine-4-carbonyl]-2,2,6,6-tetramethyl-tetrahydropyran-3,5-dione. These additional agents may also be present in the form of their esters or salts.

[0135] The compounds of the present invention can also be combined with herbicide safeners. Examples of herbicide safeners include, but are not limited to, benoxacor, cloquintocet (including cloquintocet-mexyl), cyprosulfamide, dichlormid, fenchlorazole (including fenchlorazole-ethyl), fenclorim, fluxofenim, furilazole, isoxadifen (including isoxadifen-ethyl), mefenpyr (including mefenpyr-diethyl), metcamifen, N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide and oxabetrinil; all of these can be in the form of their esters or salts.

[0136] The compounds of the present invention may also be used in mixtures with other pesticides, such as fungicides, nematicides or insecticides, examples of which will be known to those skilled in the art.

[0137] The mixing ratio of the compound of the present invention to the additional agent is preferably 1:100 to 1000: 1. The mixing ratio of the compound of the present invention to the safener is preferably 100:1 to 1:10, particularly 20:1 to 1:1.

[0138] Said mixtures can advantageously be used in the abovementioned formulations (in which case "active ingredient" relates to the respective mixture of the compound of the invention and the additional agent).

[0139] Herbicidal activity In various embodiments, the present invention provides compounds and compositions, including any of the embodiments 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 utility in 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 in which the compounds of the present invention are being applied.

[0140] The compounds of the present invention are useful as pesticides and / or herbicides, or as pesticidal and / or herbicidal compounds.Therefore, the present invention further comprises a method for controlling undesirable plant growth, which comprises applying an effective amount of the compounds according to the present invention or its agrochemical composition to useful plants or to the locus containing them under conditions effective for controlling undesirable plant growth (particularly weed growth) in the crop of useful plants.

[0141] In various embodiments, the present invention is directed to a method of controlling undesirable plant growth, which comprises applying to the plants or to a locus containing them an effective amount of a compound according to the present invention or an agrochemical composition thereof under conditions effective to control undesirable plant growth, particularly weed growth, in a crop of useful plants.

[0142] In some embodiments, "controlling" according to the present invention refers to killing, reducing or slowing the growth of the plant, or preventing or reducing germination. Generally, the plants to be controlled are undesirable plants (weeds).

[0143] In some embodiments, "locus" refers to the area in which a plant is growing or will grow.

[0144] The application rates of the compounds of the invention may vary within wide limits and may depend on the nature of the soil, the method of application (e.g. pre-planting, pre-emergence, post-emergence, application in the seed furrow, no-till application, etc.), the crop plant, the weeds to be controlled, the prevailing climatic conditions, as well as on the application method, application time and other factors governed by the target crop. The compounds of the invention are generally applied at rates of 10 to 2000 g / ha, in particular 50 to 1000 g / ha.

[0145] In some embodiments, the application is carried out by spraying the composition, typically with a tractor-mounted sprayer for large areas, although other methods such as scattering (in the case of powders), drip or drench can also be used.

[0146] In some embodiments, useful plants for which the compositions according to the present invention may be used include crops such as cereals (including, but not limited to, barley and wheat), cotton, oilseed rape, sunflower, corn, rice, soybean, sugar beet, sugarcane, and turfgrass.

[0147] In some embodiments, crop plants include trees such as fruit trees, palm trees, coconut trees, or other nuts, as well as vines such as grapes, fruit shrubs, fruit herbs, and vegetables.

[0148] In some embodiments, the crop is a resistant crop.Accordingly, in some embodiments, the crop also includes crops that are made resistant to herbicides or classes of herbicides (including but not limited to ALS, GS, EPSPS, PPO, ACCase and HPPD inhibitors) by traditional breeding or by genetic engineering.Examples of crops that are made resistant to herbicides by genetic engineering include but are not limited to glyphosate-resistant corn varieties and glufosinate-resistant corn varieties sold under the trade names RoundupReady® and LibertyLink®.In other embodiments, the crop also includes crops that are made resistant to pests by genetic engineering, examples of which include but are not limited to Bt corn (resistant to European pine moth), Bt cotton (resistant to Mexican boll weevil) and Bt potato (resistant to Colorado potato beetle). Non-limiting examples of Bt corn include NK® (Syngenta Seeds) Bt176 corn hybrids. Non-limiting examples of transgenic plants containing one or more genes encoding insecticide resistance and expressing one or more toxins are KnockOut® (corn), Yield Gard® (corn), NuCOTIN33B® (cotton), Bollgard® (cotton), NewLeaf® (potato), NatureGard®, and Protexcta®. Crop plants or their seed material can exhibit both resistance to herbicides and simultaneously resistance to insect feeding ("stacked" transgenic events).

[0149] In some embodiments, crop plants include those obtained by conventional breeding methods or by genetic engineering and that contain so-called output traits (e.g., improved storage stability, higher nutritional value, and improved flavor). Other useful plants include, for example, turfgrass in golf courses, lawns, parks, and roadsides, or commercially grown for cutting, and ornamental plants such as flowers or shrubs.

[0150] Herbicidal compounds or chemically active herbicides can be classified into pre-plant, pre-emergence and post-emergence herbicides. Pre-plant 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 weed seeds have germinated and weed growth has begun.

[0151] When the compounds of the invention are applied, they can be applied preplant or preemergence, postemergence, or both.

[0152] In various embodiments, the present invention is directed to a method for controlling the growth of undesirable plants, wherein the method comprises applying a compound according to the present invention or its agrochemical composition to a crop field. In some embodiments, the compound is a pre-plant herbicide. In some embodiments, the compound is a pre-emergence herbicide. In some embodiments, the compound is a post-emergence herbicide. Thus, in some embodiments, the compound is applied to the crop field before undesirable plants emerge (i.e., a pre-emergence herbicide or a pre-plant herbicide). In some embodiments, the compound is applied to the crop field after undesirable plants emerge (i.e., a post-emergence herbicide).

[0153] In various embodiments, the present invention is directed to a method for controlling the growth of undesirable plants, wherein the method comprises applying a compound according to the present invention or its agrochemical composition to a field containing a useful crop.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.Thus, in some embodiments, the compound is applied to the crop field before the emergence of undesirable plants (i.e., a pre-emergence herbicide or a pre-planting herbicide).In some embodiments, the compound is applied to the crop field after the emergence of undesirable plants (i.e., a post-emergence herbicide).

[0154] In various embodiments, the compounds according to the invention and their pesticide compositions are used to control undesirable vegetation, including a wide variety of monocotyledonous and dicotyledonous weed species.

[0155] In some embodiments, the undesirable plants are weeds. In some embodiments, the undesirable plants are eudicotyledonous (dicotyledonous or dicot). In some embodiments, the undesirable plants are monocotyledonous (monocotyledonous or monocot).

[0156] Non-limiting examples of monocotyledonous plant species that may typically be 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 of which represents a separate embodiment of the present invention.

[0157] Non-limiting examples of dicotyledonous plant species that may be controlled include Abutilon theophrasti, Amaranthus retroflexus, Bidens pilosa, Chenopodium album, Euphorbia heterophylla, Galium aparine, Ipomoea hederacea, Kochia scoparia, Polygonum convolvulus, Sida spinosa, Sinapis arvensis, Solanum nigrum, Stellaria media, Veronica persica, and Xanthium strumarium, each of which represents a separate embodiment of the present invention.

[0158] In some embodiments, the undesirable plant is Abutilon theophrasti, Amaranthus palmeri, Ambrosia artemisiifolia, Alopecurus myosuroides, Avena sterilis, Chenopodium album, Conyza Canadensis, Digitaria 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 any one of the compounds listed in Table 1; each compound represents a separate embodiment according to the present invention.

[0159] In some embodiments, compounds and compositions according to the present invention are utilized to control undesirable vegetation in rice. In certain embodiments, the undesirable vegetation is Brachiaria platyphylla (Groseb.) Nash (big-leaved signal grass, BRAPP), Digitaria sanguinalis (L.) Scop. (large burgrass, DIGSA), Echinochloa crus-galli (L.) P. Beauv. (barnyardgrass, ECHCG), Echinochloa colonum (L.) LINK (barnyardgrass, ECHCO), Echinochloa oryzoides (Ard.) Fritsch (early watergrass, ECHOR), Echinochloa oryzicola (Vasinger) Vasinger (late watergrass, ECHPH), Ischaemum rugosum Salisb. (salamola grass, ISCRU), Leptochloa chinensis (L.) Nees (grassgrass, LEFCH), 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. (Scion juncoides, SCPJU), Schoenoplectus maritimus L. (Sea crab rush, SCPMA), Schoenoplectus mucronatus L.(Inada Hutoi, SCPMU), Aeschynomene species, (Aeschynomene, AESSS), Alternanthera philoxeroides (Mart.) Griseb. (Alternative Weed, ALRPH), Alisma plantago-aquatica L. (Ardisia cratae, ALSPA), Amaranthus species (Pigweed and Amaranth, AMASS), Ammannia coccinea Rottb. (Little Lythrum salicaria, AMMCO), Eclipta alba (L.) Hassk. (American Eucalyptus, ECLAL), Heteranthera limosa (SW.) Willd. / Vahl (American Monarch, HETLI), Heteranthera reniformis R.&P. (Water Hyacinth, HETRE), Ipomoea hederacea (L.) Jacq. (American morning glory, IPOHE), Lindernia dubia (L.) Pennell (American dubia, LIDDU), Monochoria korsakowii Regel & Maack (Water hyacinth, MOOKA), Monochoria vaginalis (Burm.F.) C.Presl ex Kuhth, (Common weed, MOOVA), Murdannia nudifiora (L.) Brenan (Common weed, MUDNU), Polygonum pensylvanicum L. (Pennsylvania burdock, POLPY), Polygonum persicaria L. (Polygonum persicaria, POLPE), Polygonum hydropiperoides Michx. (POLHP, Mild sweetweed), Rotala indica (Willd.) Koehne (Rotin), Sagittaria species (Arrowhead, SAGSS), Sesbania exaltata (Raf) Cory / Rydb.Ex Hill (Hemp Sesbania, SEBEX) or Sphenoclea zeylanica Gaertn.(Gooseweed, SPDZE); each of which represents a separate embodiment of the present invention. In some embodiments, the compound is any one of the compounds listed in Table 1; each compound represents a separate embodiment of the present invention.

[0160] In some embodiments, compounds and compositions according to the present invention are utilized to control undesirable vegetation in cereals. In certain embodiments, the undesirable vegetation is Alopecurus myosuroides Huds. (black foxtail, ALOMY), Apera spica-venti (L.) Beauv. (windgrass, APESV), Avena fatua L. (browngrass, AVEFA), Bromus tectorum L. (browngrass, BROTE), Lolium multiflorum Lam. (mouse grass, LOLMU), Phalaris minor Retz. (fewer canary grass, PHAMI), Poa annua L. (annual bluegrass, POAAN), Setaria pumila (Poir.) Roemer & J.A. Schultes (yellow foxtail, SETLU), Setaria viridis (L.) Beauv. (green foxtail, SETVI), 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. (Papaver, 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 of which represents a separate embodiment of the present invention.In some embodiments, the compound is any one of the compounds listed in Table 1; where each compound represents a separate embodiment of the present invention.

[0161] In some embodiments, compounds and compositions according to the present invention are utilized to control undesirable vegetation in rangelands and pastures. In certain embodiments, the undesirable vegetation is selected from the group consisting of Ambrosia artemisiifolia L. (ragweed, AMBEL), Cassia obtusifolia (snake grass, CASOB), Centaurea maculosa auct. non Lam. (spotted cornflower, CENMA), Cirsium arvense (L.) Scop. (Canada thistle, CIRAR), Convolvulus arvensis L. (fieldweed, CONAR), Euphorbia esula L. (fieldweed, EPHES), Lactuca serriola L. / Tom. (spiny lettuce, LACSE), Plantago lanceolata L. (plantain, PLALA), Rumex obtusifolius L. (rhumbweed, RUMOB), Sida spinosa L. (prickly fern, SIDSP), Sinapis arvensis L. (wild mustard, SINAR), Sonchus arvensis L. (Taiwan mustard, SONAR), Solidago species (Sooss), Taraxacum officinale GHWeber ex Wiggers (Common dandelion, TAROF), Trifolium repens L. (White clover, TRFRE), or Urtica dioica L. (Nettle, URTDI); each of which represents a separate embodiment in accordance with the present invention. In some embodiments, the compound is any one of the compounds listed in Table 1; each of which represents a separate embodiment in accordance with the present invention.

[0162] In some embodiments, compounds and compositions according to the present invention are utilized to control undesirable vegetation found in row crops. In certain embodiments, the undesirable vegetation is Alopecurus myosuroides Huds. (black foxtail, ALOMY), Avena fatua L. (brown grass, AVEFA), Brachiaria platyphylla (Groseb.) Nash (big-leaved signal grass, BRAPP), Digitaria sanguinalis (L.) Scop, (large burdock, DIGSA), Echinochloa crus-galli (L.) P. Beauv. (dog shrimp, ECHCG), Echinochloa colonum (L.) Link (barnyard millet, ECHCO), Lolium multiflorum Lam. (mouse barley, LOLMU), Panicum dichotomiflorum Michx. (big-leaved grass, PANDI), Panicum miliaceum L. (wild millet, PANMI), 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.(Canada thistle, CIRAR), Commelina benghalensis L. (Combe), Datura stramonium L. (Datst), Daucus carota L. (Duca leek, DAUCA), Euphorbia heterophylla L. (Wild poinsettia, EPHHL), Erigeron bonariensis L. (Rough ragweed, ERIBO), Erigeron canadensis L. (Erica), Helianthus annuus L. (Sunflower, HELAN), Jacquemontia tamnifolia (L.) Griseb. (Morning glory, IAQTA), Ipomoea hederacea (L.) Jacq. (American morning glory, IPOHE), Ipomoea lacunosa L. (morning glory, IPOLA), Lactuca serriola L. / Tom. (lettuce, LACSE), Portulaca oleracea L. (speril, POROL), Sida spinosa L. (prickly fern, SIDSP), Sinapis arvensis L. (wild mustard, SINAR), Solanum ptychanthum Dunal (eastern black nightshade, SOLPT) or Xanthium strumarium L. (cocklebur, XANST); each of which represents a separate embodiment in accordance with the present invention. In some embodiments, the compound is any one of the compounds listed in Table 1; each of which represents a separate embodiment in accordance with the present invention.

[0163] The following examples are presented in order to more fully illustrate the preferred embodiments of the invention, but they should not be construed as limiting the broad scope of the invention. EXAMPLES

[0164] Working Example Example 1 Synthetic Details for Compounds of the Invention Preparation of Compound 101 Scheme 1. Preparation of Compound 101 [ka] General procedure for preparing compound 2 (Scheme 1) [ka] To a solution of compound 1 (255 g, 2.21 mol, 1.00 eq) in dioxane (1500 mL) was added NaOH (97.5 g, 2.44 mol, 1.10 eq) and H2O (1500 mL). After 10 min, Boc2O (580 g, 2.66 mol, 1.20 eq) was added. The mixture was stirred at 25 °C for 4 h. LC-MS showed that reactant 1 was completely consumed and one major peak with the desired mass was detected. The reaction mixture was diluted with H2O (1500 mL), washed with MTBE (1500 mL) and the organic phase was discarded. The aqueous phase was adjusted to pH 3 with aqueous 1 M HCl and then extracted with EtOAc (2000 mL x 2). The combined organic layers were washed with brine (2000 mL), dried over MgSO4, filtered and concentrated under reduced pressure to give compound 2 (384 g, 1.78 mol, 80.5% yield) as a white solid, which was used in the next step without further purification.

[0165] 1 H NMR (400 MHz, DMSO-d6) δ 13.73 - 11.10 (m, 1H), 7.01 (d, J = 8.1 Hz, 1H), 5.75 (tdd, J = 6.9, 10.1, 17.0 Hz, 1H), 5.17 - 4.96 (m, 2H), 3.92 (dt, J = 5.1, 8.5 Hz, 1H), 2.46 - 2.22 (m, 2H), 1.37 (s, 9H) General procedure for preparing compound 3 (Scheme 1) [ka] To a solution of compound 2 (380 g, 1.77 mol, 1.00 eq) in DCM (4000 mL) was added CDI (372 g, 2.30 mol, 1.30 eq) in small portions. The mixture was stirred at 20° C. for 0.5 h. N-Methoxymethylamine hydrochloride (258 g, 2.65 mol, 1.50 eq) was then added and stirred at 25° C. for 5 h. LC-MS showed that reactant 2 was completely consumed and one major peak with the desired mass was detected. The reaction mixture was diluted with DCM (3000 mL), washed with 1 M HCl (2000 mL) and saturated NaHCO3 (2000 mL) and brine (2000 mL), dried over MgSO4, filtered and concentrated under reduced pressure to give crude compound 3 (350 g, 1.35 mol, 76.8% yield) as a white solid. This was used in the next step without further purification.

[0166] 1 H NMR: (400 MHz, DMSO-d6) δ 7.00 (br d, J = 8.3 Hz, 1H), 5.82 - 5.67 (m, 1H), 5.14 - 4.97 (m, 2H), 4.54 - 4.25 (m, 1H), 3.72 (s, 3H), 3.09 (s, 3H), 2.33 - 2.17 (m, 2H), 1.36 (s, 9H) General procedure for preparing compound 4 (Scheme 1) [ka] To a solution of compound 3 (120 g, 465 mmol, 1.00 eq) in THF (1700 mL) was added BrMgMe (3 M, 619 mL, 4.00 eq) at -5°C. The mixture was stirred at -5°C for 2 h. TLC (petroleum ether:THF=10:1 SM R f =0.64 product R f=0.82) indicated that compound 3 was completely consumed and one new spot was formed. The reaction was free of impurities by TLC. The reaction solution was poured into ice-cold 10% NH4Cl (1000 mL) and extracted with EtOAc (1000 mL x 3). The combined organic layers were washed with brine (800 mL), dried over MgSO4, filtered, and concentrated under reduced pressure to give a residue. The residue was purified by flash silica gel chromatography (ISCO®; 330+330 g SepaFlash® silica flash column, eluent 0-4% ethyl acetate / petroleum ether gradient @ 100 mL / min). Compound 4 (84.0 g, 394 mmol, 84.8% yield) was obtained as a colorless oil.

[0167] 1 H NMR: (400 MHz, DMSO-d6) δ 7.13 (br d, J = 7.6 Hz, 1H), 5.82 - 5.71 (m, 1H), 5.69 (s, 1H), 5.15 - 4.95 (m, 2H), 2.47 - 2.16 (m, 2H), 2.07 (s, 3H), 1.45 - 1.31 (m, 9H) General procedure for preparing compound 5 (Scheme 1) [ka] To a solution of compound 4 (113 g, 530 mmol, 1.00 eq) in MeOH (1200 mL), NaBH4 (50.1 g, 1.32 mol, 2.50 eq) was added in small portions at 20° C. The mixture was stirred at 20° C. for 2 h. TLC (petroleum ether:THF=3:1 SM R f =0.80 Product R f=0.29) indicated complete consumption of reactant 4 and the formation of one new spot. The reaction mixture was quenched by adding H2O (1500 mL) at 5 °C, and the reaction mixture was extracted with EtOAc (800 mL x 2). The combined organic layers were washed with brine (600 mL), dried over MgSO4, filtered, and concentrated under reduced pressure to give a residue. The residue was purified by flash silica gel chromatography (ISCO®; 330+330 g SepaFlash® silica flash column, eluent 0-18% THF / petroleum ether gradient @ 100 mL / min). Compound 5 (185 g, 859 mmol, 81.1% yield) was obtained as a white solid.

[0168] 1 H NMR: (400 MHz, DMSO-d6) δ 6.54 - 6.06 (m, 1H), 5.80 - 5.63 (m, 1H), 5.10 - 4.90 (m, 2H), 4.68 - 4.44 (m, 1H), 3.47 - 3.37 (m, 1H), 3.29 - 3.12 (m, 1H), 2.43 - 1.92 (m, 2H), 1.43 - 1.29 (m, 9H), 1.07 - 0.92 (m, 3H) General procedure for preparing compound 7 (Scheme 1) [ka] A solution of compound 5 (59.0 g, 274 mmol, 1.00 eq) and compound 6 (32.9 g, 329 mmol, 1.20 eq) in DCM (700 mL) was placed under vacuum for 30 min and purged with N2 three times, then GRUB2' (4.65 g, 5.48 mmol, 0.02 eq) was added and the mixture was placed under vacuum for 10 min and purged with N2 three times. The mixture was stirred at 50 °C for 4 h. TLC (petroleum ether:ethyl acetate=2:1.5, SM R f =0.45, product R f=0.25) indicated that about 15% of reactant 5 remained and one major new spot (about 40%) that was more polar was detected. The reaction mixture was filtered, washed with DCM (200 mL x 3), and the filtrate was concentrated under reduced pressure to remove the solvent. The residue was purified by column chromatography (SiO2, ethyl acetate / petroleum ether = 15%-21%). Compound 7 (119 g, 414 mmol, 50.4% yield) was obtained as a yellow oil.

[0169] 1 H NMR: (400 MHz, CDCl3) δ 5.71 - 5.50 (m, 2H), 4.96 - 4.52 (m, 1H), 3.93 - 3.79 (m, 1H), 3.76 - 3.66 (m, 3H), 3.63 (br s, 1H), 3.19 - 3.00 (m, 2H), 2.43 - 2.22 (m, 3H), 1.44 (s, 9H), 1.23 - 1.10 (m, 3H). General procedure for preparing compound 8 (Scheme 1) [ka] To a solution of compound 7 (119 g, 414 mmol, 1.00 eq) in THF (700 mL) and HO (700 mL) was added LiOH.HO (69.5 g, 1.66 mol, 4.00 eq). The mixture was stirred at 20 °C for 1 h. TLC (petroleum ether:ethyl acetate = 1:1, SMR) showed that the elution was stable and the elution time was 1 h. f =0.50, product R f=0.00) indicated complete consumption of reactants. The reaction mixture was diluted with H2O (800 mL) and extracted with EtOAc (500 mL x 2), and the organic layer was discarded. The aqueous layer was adjusted to pH 3 with 1M HCl and extracted with EtOAc (800 mL x 3). The combined organic layers were washed with brine (800 mL), dried over MgSO4, filtered, and concentrated under reduced pressure to give a residue (ca. 120 g). The crude product was purified by recrystallization from MTBE (500 mL) at 50 °C, then stirred at 15 °C for 16 h, and filtered to give 24 g of product. The filtrate was concentrated under reduced pressure and purified by recrystallization from i-Pr2O (500 mL) at 50 °C, then stirred at 15 °C for 16 h, and filtered to give 26 g of product. The products were combined, triturated with i-Pr2O (1000 mL) at 15 °C for 1 h, and filtered to give compound 8 (42.0 g, 154 mmol, 37.1% yield) as a white solid.

[0170] 1 H NMR: (400 MHz, CDCl3) δ 5.68 - 5.53 (m, 2H), 5.04 - 4.47 (br, 1H), 3.95 - 3.76 (m, 1H), 3.73 - 3.45 (m, 1H), 3.09 (d, J = 5.1 Hz, 2H), 2.37 - 2.24 (m, 1H), 2.24 - 2.11 (m, 1H), 1.44 (s, 9H), 1.17 (J = 6.4 Hz, 3H). General procedure for preparing compound 101 (Scheme 1) [ka] To a solution of compound 8 (40.0 g, 146 mmol, 1.00 eq) in dioxane (300 mL) was added HCl / dioxane (4 M, 137 mL, 3.74 eq). The mixture was stirred at 20° C. for 16 h. The reaction mixture was concentrated under reduced pressure to give a residue. The residue was diluted with pure HO (200 mL) and washed with EtOAc (200 mL×3). The aqueous layer was lyophilized to give compound 101 (31.5 g, 144 mmol, 98.1% yield, 95.6% purity, HCl) as a yellow oil.

[0171] 1 H NMR: (400 MHz, DMSO-d6) δ 13.24 - 11.15 (m, 1H), 7.98 (br s, 3H), 5.74 - 5.57 (m, 1H), 5.57 - 5.43 (m, 1H), 4.99 (br dd, J = 3.4, 6.3 Hz, 1H), 3.86 (br dd, J = 3.5, 6.3 Hz, 1H), 3.11 - 3.02 (m, 1H), 2.99 (br d, J = 6.4 Hz, 2H), 2.37 - 2.20 (m, 2H), 1.08 (br d, J = 6.5 Hz, 3H). Compound 172 was prepared using techniques similar to those described for compound 101.

[0172] Preparation of Compound 110 Scheme 2: Preparation of compound 110 [ka] General procedure for preparing compound 2 (Scheme 2) [ka] To a solution of compound 1 (50.0 g, 375 mmol) in THF (200 mL) was added Boc2O (123 g, 563 mmol) and TEA (114 g, 1.13 mol). The mixture was stirred at 20 °C for 16 h. LC-MS showed that reactant 1 was completely consumed and one major peak with the desired mass was detected. The reaction mixture was diluted with water (1000 mL) and extracted with EtOAc (1000 mL x 3). The combined organic layers were washed with brine (500 mL), dried over MgSO4, filtered and concentrated under reduced pressure to give a residue. Compound 2 (85 g, 97.0% yield) was obtained as a colorless oil, which was used in the next step without further purification.

[0173] 1 H NMR (400 MHz, chloroform-d) δ 5.48 (br s, 1H), 4.35 (br d, J = 3.1 Hz, 1H), 4.12 - 4.08 (m, 1H), 3.76 (s, 3H), 3.18 (br d, J = 5.5 Hz, 1H), 1.43 (s, 9H), 1.21 - 1.15 (m, 3H) General procedure for preparing compound 3 (Scheme 2) [ka] To a solution of compound 2 (40.0 g, 171 mmol) and compound 2_1 (178 g, 1.71 mol) in toluene (400 mL) was added TsOH (4.43 g, 25.7 mmol). The mixture was stirred at 80 °C for 4 h. LC-MS showed that reactant 2 was completely consumed and one major peak with the desired mass was detected. The reaction mixture was concentrated under reduced pressure to remove the solvent. The residue was diluted with aqueous NaHCO3 (500 mL) and extracted with MTBE (250 mL x 3). The combined organic layers were washed with brine (300 mL), dried over MgSO4, filtered, and concentrated under reduced pressure to give a residue. The crude compound 3 (30.0 g, 64.0% yield) was obtained as a yellow oil, which was used in the next step without further purification.

[0174] 1 H NMR: (400 MHz, chloroform-d) δ 4.45 - 4.24 (m, 2H), 3.75 (s, 3H), 1.72 (d, J = 15.6 Hz, 3H), 1.54 - 1.47 (m, 8H), 1.41 (s, 5H), 1.27 - 1.22 (m, 3H) General procedure for preparing compound 4 (Scheme 2) [ka] To a solution of compound 3 (20.0 g, 73.17 mmol) in THF (250 mL), LAH (4.17 g, 110 mmol) was added at 0° C. The mixture was stirred at −10° C. for 1 h. TLC (petroleum ether:ethyl acetate=10:1, R f =0.07) indicated complete consumption of reactant 3 and the formation of a new spot. The mixture was quenched with HO (4 mL) and 15% NaOH (4 mL), filtered, and concentrated under reduced pressure to give a residue. Compound 4 (12.5 g, 69.6% yield) was obtained as a yellow oil, which was used in the next step without further purification.

[0175] 1 H NMR: (400 MHz, DMSO-d6) δ 4.64 (br s, 1H), 4.28 - 4.14 (m, 1H), 3.76 - 3.56 (m, 1H), 3.50 - 3.37 (m, 2H), 1.41 (br d, J = 3.5 Hz, 15H), 1.22 (d, J = 6.5 Hz, 3H) General procedure for preparing compound 5 (Scheme 2) [ka] To a solution of compound 4 (12.5 g, 50.9 mmol) in DCM (200 mL) was added DMP (25.9 g, 61.2 mmol). The mixture was stirred at 25° C. for 16 h. TLC (petroleum ether:ethyl acetate=10:1, R f=0.41) indicated complete consumption of reactant 4 and the formation of one new spot. The reaction mixture was filtered and concentrated under reduced pressure to give a residue. The residue was purified by flash silica gel chromatography (ISCO®; 220 g SepaFlash® Silica Flash column, eluent 0-10% ethyl acetate / petroleum ether gradient @ 100 mL / min). Compound 5 (7.01 g, 56.4% yield) was obtained as a yellow oil.

[0176] 1 H NMR: (400 MHz, DMSO-d6) δ 9.58 (dd, J = 2.5, 5.4 Hz, 1H), 4.45 (quin, J = 6.5 Hz, 1H), 4.27 (td, J = 3.0, 6.5 Hz, 1H), 1.59 (s, 3H), 1.50 - 1.40 (m, 9H), 1.33 (s, 5H), 1.20 (dd, J = 3.3, 6.4 Hz, 3H) General procedure for preparing compound 6 (Scheme 2) [ka] To a solution of compound 5 (3.5 g, 14.4 mmol) and compound 5_1 (4.68 g, 18.7 mmol,) dissolved in toluene (60.0 mL), K2CO3 (3.98 g, 28.8 mmol) and 18-crown-6 (380 mg, 1.44 mmol) were added. The mixture was stirred at 25 °C for 16 h. TLC (petroleum ether: ethyl acetate = 10:1, R f=0.39) indicated complete consumption of reactant 5 and the formation of one new spot. The reaction mixture was diluted with water (100 mL) and extracted with EtOAc (100 mL x 3). The combined organic layers were washed with brine (100 mL), dried over MgSO4, filtered, and concentrated under reduced pressure to give a residue. The residue was purified by flash silica gel chromatography (ISCO®; 40 g SepaFlash® Silica Flash column, eluent 0-10% ethyl acetate / petroleum ether gradient @ 50 mL / min). Compound 6 (3.15 g, 64.5% yield) was obtained as a yellow oil.

[0177] 1 H NMR: (400 MHz, chloroform-d) δ 9.54 - 9.44 (m, 1H), 7.29 - 7.16 (m, 1H), 6.31 - 6.09 (m, 1H), 5.93 - 5.76 (m, 2H), 4.38 - 4.05 (m, 4H), 1.49 - 1.45 (m, 3H), 1.44 - 1.38 (m, 6H), 1.34 - 1.30 (m, 6H), 1.27 - 1.19 (m, 4H), 1.09 (d, J = 6.3 Hz, 3H) General procedure for preparing compound 7 (Scheme 2) [ka] To a solution of compound 6 (1.00 g, 2.95 mmol) in THF (5 mL) and HO (5 mL) was added LiOH (353 mg, 14.7 mmol). The mixture was stirred at 25 °C for 2 h. TLC (petroleum ether:ethyl acetate = 10:1, R f=0.52) indicated that reactant 6 was completely consumed and one major peak with the desired mass was detected. The reaction mixture was diluted with H2O (50 mL), extracted with EtOAc (50 mL x 2), and the organic layer was discarded. The aqueous layer was adjusted to pH 2 with 2M HCl and then extracted with EtOAc (50 mL x 2). The combined organic layers were washed with brine (50 mL), dried over MgSO4, filtered, and concentrated under reduced pressure to give a residue. The residue was purified by flash silica gel chromatography (ISCO®; 20 g SepaFlash® Silica Flash column, eluent 0-25% ethyl acetate / petroleum ether gradient @ 30 mL / min). Compound 7 (0.52 g, 56.7% yield) was obtained as a yellow oil.

[0178] 1 H NMR (400 MHz, chloroform-d) δ 7.38 (td, J = 11.4, 15.2 Hz, 1H), 6.44 - 6.17 (m, 1H), 6.00 (br dd, J = 8.4, 15.0 Hz, 1H), 5.90 (d, J = 15.4 Hz, 1H), 4.42 - 4.20 (m, 2H), 4.20 - 4.08 (m, 1H), 1.70 - 1.52 (m, 6H), 1.51 - 1.37 (m, 10H), 1.33 - 1.24 (m, 1H), 1.18 (d, J = 6.4 Hz, 3H) General procedure for preparing compound 110 (Scheme 2) [ka] Compound 7 (500 mg, 1.61 mmol) was dissolved in 4M HCl / dioxane (3 mL) and dioxane (3 mL). The mixture was stirred at 25 °C for 16 h. LC-MS showed that reactant 7 was completely consumed and one major peak with the desired mass was detected. The reaction mixture was concentrated under reduced pressure to give a residue. The residue was dissolved in HO (20 mL), washed with EtOAc (20 mL x 2), and the aqueous layer was lyophilized to give compound 110 (205 mg, 74.5% yield) as an orange gum.

[0179] 1 H NMR (400 MHz, DEUTERIUM OXIDE) δ 7.42 - 7.24 (m, 1H), 6.70 - 6.53 (m, 1H), 6.22 - 6.00 (m, 2H), 4.17 - 4.06 (m, 1H), 3.99 - 3.86 (m, 1H), 3.79 - 3.71 (m, 1H), 3.81 - 3.70 (m, 1H), 1.25 - 1.12 (m, 3H) Example 2 General synthetic scheme for compounds of the present invention General scheme for the synthesis of compound 154 and compound 167 Scheme 3. General scheme for preparing compounds 154 and 167. [ka] Compounds 154 and 167 were synthesized by reacting an alkyne-containing aliphatic carboxylic acid with a cyclohexylamine bearing a halogen substituent as described by Zwikker et al. (Scheme 3). The expected yield of this reaction is 71%.

[0180] General scheme for synthesizing Compound 169, Compound 170, Compound 112, Compound 125, Compound 146, Compound 157, and Compound 166 Scheme 4. General scheme for preparing compound 169 [ka] Compound 169 is synthesized by reacting hex-5-en-2-one with hydroxylamine, followed by reduction with LAH to give hex-5-en-2-amine, which is further reacted with but-3-enoic acid and Grubbs' catalyst (Scheme 4).

[0181] Compounds 170, 112, 125, 146, 157 and 166 are prepared in a similar manner by appropriately substituting the starting ketone and carboxylic acid (Scheme 4).

[0182] Example 3 Herbicidal Activity Data Application to weed panels The herbicidal activity of the compounds (active ingredients; AI) was demonstrated by the following greenhouse experiments.

[0183] In planta low-throughput screening (LTP) results Post-occurrence processing A base panel of eight weed species (Table 3) was sown in 4 x 4 x 7 cm plastic pots containing garden mix (klasmann). Each weed species was sown in a separate pot. Each pot was sown with 10-15 seeds according to the survival rate of the weed species. 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 day, 20 ± 2 °C night). Flood irrigation (tap water + Shefer 5:3:8 8 mM) was provided at a water content of 50% by weight. Two days before application, test plants were thinned to 3 plants per pot. Compounds were dissolved in water (DDW) and commercial herbicide control was dissolved in formulation B (Table 4). Prior to application, the solution was diluted with 1% (v / v) crop oil and 0.02% (v / v) surfactant (Tergitol TM15-S-7) was added. Application was performed with an industrial sprayer (TeeJet 6502E nozzle) at a rate of 2 kg / ha with a spray volume of 480 L / ha. Plants were evaluated at three time points: 4, 8, and 12 days after application (DAA). At each time point, visual phenotype was recorded using a scale of 0 to 6 (0: no visible effect, 6: maximum effect). At 12 DAA, the shoots of the plants were harvested, dried and weighed for dry weight analysis.

[0184] Advanced Post-emergence The dose-response experiment included four species: SETVI, ECHCO, AMAPA, and ABUTH (Table 3, Table 5). Applications were at six rates between 0.6 and 0.0187 kg / ha and a spray volume of 480 L / ha. Plants were evaluated at four time points (6, 12, 18, and 26 DAA). At each time point, visual phenotypes were recorded using a 0-6 scale (0: no visible effect, 6: maximum effect). At 26 DAA, plant foliage was harvested, dried and weighed for dry weight analysis.

[0185] Advanced post-emergence wide panel The experiment included 24 weed species (Table 5). Applications were at two rates, 2 kg / ha and 0.25 kg / ha, and 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, plant foliage was 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 for visual phenotypes was determined by median of ≥ 3.5 and Fisher's test (p-value ≤ 0.05). Statistical analysis for dry weight was determined by % inhibition ≥ 50 and T-test (p-value ≤ 0.05) and Wilcox's test (p-value ≤ 0.05).

[0186] Pre-emergence treatment A base panel of eight weed species (Table 3) was sown in 4 x 4 x 7 cm plastic pots containing inert sand (Sweet sand) and intensively washed using percolation water. Each weed species was sown in a separate pot. Each pot was sown with 10-15 seeds according to the survival rate of the weed species. Sowing was done 1 day before application. Plants were grown for 21 days in a controlled greenhouse (26 ± 2 °C day, 20 ± 2 °C night). Flood irrigation (tap water + Shefer 5:3:8 8 mM) was provided at a water content of 50% by weight. Compounds were dissolved in water (DDW) and commercial herbicide control was dissolved in formulation B (Table 4). Application was performed with an industrial sprayer (TeeJet 6502E nozzle) at a rate of 2 kg / ha with a spray volume of 480 L / ha.

[0187] Advanced pre-emergence Dose-response experiments were performed at six application rates between 1 and 0.0312 kg / ha and a spray volume of 480 L / ha. The percentage of emergence was assessed at 15 DAA. Visual phenotypes were recorded at 18 DAA using a scale of 0-6 (0: no visible effect, 6: maximum effect). All experiments included an untreated control, a solvent control and a positive control (commercial herbicide AI). Statistical analysis of visual phenotypes was determined by median ≥ 3.5 and Fisher's test (p-value ≤ 0.05). Statistical analysis of plant emergence was determined by % emergence ≥ 50 and T-test (p-value ≤ 0.05) and Wilcox's test (p-value ≤ 0.05). [Table 9] [Table 10] [Table 11] result: In planta low throughput (LTP) results for compounds 101, 110, 125, 119, 124, 146 and 154 are set forth in Table 6 below. [Table 12] The above results show excellent control of compound 101 against both monocotyledonous and eudicotyledonous weed species in both post-emergence and pre-emergence application modes for the majority of weed species tested. Compound 110 shows good to moderate activity against dicotyledonous and monocotyledonous weeds when applied pre-emergence. In addition, compounds 125, 119, 124, 146 and 154 showed very good to moderate growth inhibition, mainly in pre-emergence applications.

[0188] In planta high throughput screening (HTPS) results Postemergence applications to miniature dicotyledonous model plants. Arabidopsis thaliana seeds were sown in 96-well plates filled with irrigated Sweet Sand (10%>clay) that had been washed of salts and minerals using tap water. Five to ten seeds were sown in the center of each well. Seven to eight days after sowing, thinning was performed at the two true leaf stage to ensure that compound applications were made to a single plant per well. The plates were placed in random order in a controlled greenhouse in a tank that allowed for flood irrigation with tap water supplemented with fertilizer. Compounds to be applied were dissolved in a final solution consisting of 50% acetone, 49.9% DDW, 0.1% Tween 20.

[0189] A 96-well plate was used as a stock plate to prepare application solutions for 8 replicates. Each row contained a different concentration for each chemical. The highest 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 of each well using a 12-channel pipette. Data collection: RGB (red, green, blue) data for green area per well were recorded using a camera. Data were collected at several time points during the experimental period: 1 day after thinning and before chemical application, 2 days, 6 days or 9 days after application. Visual phenotypic examination was performed between the last two recordings. Data analysis: RGB results and visual phenotypic scores were obtained, and Student's t-tests were performed to compare between treatment and control performance for continuous data (RGB) and Fisher's exact test was performed to analyze non-continuous data (phenotypic scores). ED was calculated using the log concentration range of the treatment and normalized green area as dependent variables. 50 Dose-response curves are constructed for each treatment to estimate the and maximum inhibition parameters.

[0190] Preemergence applications to dicotyledonous and monocotyledonous model plants These experiments were performed similarly with the following exceptions: either Arabidopsis thaliana or Eragrostis teff seeds were sown (5-10 or 5-7 seeds, respectively), plants were not thinned, compounds were dissolved in a final solution of 50% acetone, 49.9% DDW, compound applications were made directly to the seeded soil prior to plant emergence in a volume of 30 μL per well, and data were collected 10 or 7 days after chemical application to dicotyledonous or monocotyledonous plants, respectively.

[0191] Imaging, RGB and Statistical Analysis Imaging of the plates was performed at 11 and 18 DAA. RGB data for green area per well was recorded and used to derive % inhibition. EC 50, E.C. 75 and E.C. 90 Dose-response curves were constructed for each treatment to estimate parameters. Treatments were compared to control performance using the resulting RGB results and Student's t-test (p-value ≦0.05).

[0192] result: Compounds 101, 110, 112, 119, 124, 125, 146, 154, 157, 172, 170, 169, 112 and 166 were applied to either or both of monocotyledonous and dicotyledonous model plants in either or both of the pre-emergence and post-emergence modes according to the methods described above. The compounds were applied as a gradient of concentrations as described above, from which the ED 50 was calculated.

[0193] The results of in planta high throughput screening (HTPS) for compounds 101, 110, 112, 119, 124, 125, 146, 154, 157, 172, 170, 169, 112 and 166 are shown in Table 7 below. [Table 13] The results in the table above show excellent to very good control for most of the compounds (especially compounds 101 and 110) in the systems in which they were tested.

Claims

1. Formula I: 【Chemistry 1】 [During the ceremony, C Ｉ , C ＩＩ , C ＩＩＩ and C ＩＶ These are triple bonds, double bonds, or single bonds, respectively. Depending on whether it is part of the combination, each independently is an sp carbon atom, sp ２ carbon atom or sp ３ carbon atom; and each, an sp carbon atom; sp ２ carbon atom; or sp ３ carbon atom, each independently is C; CH or C(R ２０ ); or, CH ２ , CH(R ２０ ) or C(R ２０ ) ２ ; Here, R ２０ is a halogen (e.g., F) or C １ -C ５ A linear or branched alkyl group (e.g., methyl); C Ｉ ...C ＩＩ , C ＩＩ ...C ＩＩＩ , C ＩＩＩ ...C ＩＶ Each of these is independently either a single bond or a double bond, where C Ｉ ...C ＩＩ , C ＩＩ ...C ＩＩＩ and C ＩＩＩ ...C ＩＶ At least one of them is a double bond; or C Ｉ ...C ＩＩ , C ＩＩ ...C ＩＩＩ and C ＩＩＩ ...C ＩＶ Each of these is independently a single bond or a triple bond, where C Ｉ ...C ＩＩ , C ＩＩ ...C ＩＩＩ and C ＩＩＩ ...C ＩＶ At least one of them is a triple bond; R １ H, F, Cl, Br, I, C １ -C ５ The linear or branched alkyl groups (e.g., methyl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl, benzyl); Here, C Ｉ ...C ＩＩ If R is a triple bond, １ It does not exist; R ２ F, Cl, Br, I, C １ -C ５ Linear or branched substituted or unsubstituted alkyl groups (e.g., methyl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl), C ２ -C ５ A linear or branched substituted or unsubstituted alkenyl (e.g., etenyl (CH=CH)) ２ )), C ２ -C ５ The linear or branched substituted or unsubstituted alkynyl (e.g., ethynyl (CCH)); Or, R １ and R ２ They bond to form a 3-8 member substituted or unsubstituted saturated or unsaturated carbocyclic ring B (e.g., cyclohexyl, cyclohexenyl, cyclopentyl); R ２ ' is H, F, Cl, Br, I, C １ -C ５ Linear or branched substituted or unsubstituted alkyl groups (e.g., methyl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl), C ２ -C ５ A linear or branched substituted or unsubstituted alkenyl (e.g., etenyl (CH=CH)) ２ )), C ２ -C ５ The linear or branched substituted or unsubstituted alkynyl (e.g., ethynyl (CCH)); R ３ H, F, Cl, Br, I, OH, SH, NH ２ NHR, N(R) ２ And; Or, R ３ and R ２ ' is bonded to form a 3- to 8-membered substituted or unsubstituted cycloalkyl ring C (e.g., cyclopropyl); R ４ H, F, Cl, Br, I, OH, SH, NH ２ NHR, N(R) ２ And; R ４０ H, C １ -C ５ The linear or branched alkyl groups (e.g., methyl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl); Or, R ３ and R ４０ They bond together to form a 3- to 8-membered substituted or unsubstituted cycloalkyl ring A (e.g., cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl); R ５ is a straight-chain or branched-chain, substituted or unsubstituted alkenyl of H, C ２ -C ５ ; a straight-chain or branched-chain, substituted or unsubstituted alkynyl of C ２ [[ID=,]]-C ５ (e.g., CCH, CH ２ -CCH,); a straight-chain or branched-chain haloalkyl of C １ -C ５ (e.g., CF ３ , CF ２ CH ３ , CH ２ CF ３ , CF ２ CH ２ CH ３ , CH ２ CH ２ CF ３ , CF<, ２ CH(CH ３ ) ２ , CF(CH ３ )-CH(CH ３ ) ２ ); R ８ -aryl (e.g., CH ２ -Ph), C(=CH ２ )-R １０ (e.g., C(=CH ２ )-C(O)-OCH ３ , C(=CH ２ )-CN), a substituted or unsubstituted alkylsulfone (e.g., SO ２ -CH ２ -cyclopropyl), a substituted or unsubstituted aryl (e.g., phenyl), a substituted or unsubstituted heteroaryl (e.g., pyridine (2, 3, and 4-pyridine)); X １ is O, NH, or N-R ５０ And; R ８ is [CH ２ ] ｐ And; Here, p is between 1 and 10; R １０ H, CN, C １ -C ５ Linear or branched alkyl groups (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH) ３ )) or S(O) ２ It is R; R ５０ H, C １ -C ５ The linear or branched alkyl (e.g., methyl, ethyl, butyl, i-propyl) is either substituted or unsubstituted; R is C １ -C ５ Linear or branched alkyl groups, C １ -C ５ The linear or branched alkoxy, phenyl, aryl, or heteroaryl compounds, or two geminal R substituents bond together to form a 5- or 6-membered heterocyclic ring; Ring A is either absent or a 3- to 8-membered substituted or unsubstituted cycloalkyl ring (e.g., cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl); The B ring is either absent or a 3- to 8-membered substituted or unsubstituted saturated or unsaturated carbocyclic ring (e.g., cyclohexyl, cyclohexenyl, cyclopentyl); The C ring is either absent or a 3- to 8-membered substituted or unsubstituted cycloalkyl ring (e.g., cyclopropyl); Here, at least one of rings A, B, and C is present. Compounds represented by the structure shown, or their pesticide-acceptable salts, amphotericions (internal salts), stereoisomers, tautomers, hydrates, N-oxides, reverse amide analogs, isotopic variants (e.g., deuterated analogs), or any combination thereof; Here, R ３ and R ４ At least one of them is NH ２ That is the case.

2. Formula I: 【Chemistry 2】 [During the ceremony, C Ｉ , C ＩＩ , C ＩＩＩ and C ＩＶ Depending on whether they are part of a triple bond, a double bond, or a single bond, they are independently sp carbon atoms, sp ２ carbon atoms or sp ３ It is a carbon atom; and each is a sp carbon atom; sp ２ carbon atom; or sp ３ For each carbon atom, independently, C;CH or C(R) ２０ ); or CH ２ CH(R ２０ ) or C (R ２０ ) ２ And; Here, R ２０ is a halogen (e.g., F) or C １ -C ５ A linear or branched alkyl group (e.g., methyl); C Ｉ ...C ＩＩ , C ＩＩ ...C ＩＩＩ , C ＩＩＩ ...C ＩＶ Each of these is independently either a single bond or a double bond, where C Ｉ ...C ＩＩ , C ＩＩ ...C ＩＩＩ and C ＩＩＩ ...C ＩＶ At least one of them is a double bond; or C Ｉ ...C ＩＩ , C ＩＩ ...C ＩＩＩ and C ＩＩＩ ...C ＩＶ Each of these is independently a single bond or a triple bond, where C Ｉ ...C ＩＩ , C ＩＩ ...C ＩＩＩ and C ＩＩＩ ...C ＩＶ At least one of them is a triple bond; R １ H, F, Cl, Br, I, C １ -C ５ The linear or branched alkyl groups (e.g., methyl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl, benzyl); Here, C Ｉ ...C ＩＩ If R is a triple bond, １ It does not exist; R ２ F, Cl, Br, I, C １ -C ５ Linear or branched substituted or unsubstituted alkyl groups (e.g., methyl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl), C ２ -C ５ A linear or branched substituted or unsubstituted alkenyl (e.g., etenyl (CH=CH)) ２ )), C ２ -C ５ The linear or branched substituted or unsubstituted alkynyl (e.g., ethynyl (CCH)); Or, R １ and R ２ They bond to form a 3-8 member substituted or unsubstituted saturated or unsaturated carbocyclic ring B (e.g., cyclohexyl, cyclohexenyl, cyclopentyl); R ２ ' is H, F, Cl, Br, I, C １ -C ５ Linear or branched substituted or unsubstituted alkyl groups (e.g., methyl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl), C ２ -C ５ A linear or branched substituted or unsubstituted alkenyl (e.g., etenyl (CH=CH)) ２ )), C ２ -C ５ The linear or branched substituted or unsubstituted alkynyl (e.g., ethynyl (CCH)); R ３ H, F, Cl, Br, I, OH, SH, NH ２ NHR, N(R) ２ And; Or, R ３ and R ２ ' is bonded to form a 3- to 8-membered substituted or unsubstituted cycloalkyl ring C (e.g., cyclopropyl); R ４ H, F, Cl, Br, I, OH, SH, NH ２ NHR, N(R) ２ And; R ４０ H, C １ -C ５ The linear or branched alkyl groups (e.g., methyl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl); Or, R ３ and R ４０ They bond together to form a 3- to 8-membered substituted or unsubstituted cycloalkyl ring A (e.g., cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl); R ５ H, C ２ -C ５ Linear or branched substituted or unsubstituted alkenyls, C ２ -C ５ Linear or branched substituted or unsubstituted alkynyl molecules (e.g., CCH, CH) ２ -CCH,), C １ -C ５ Linear or branched haloalkyl groups (e.g., CF ３ CF ２ CH ３ ,CH ２ CF ３ CF ２ CH ２ CH ３ ,CH ２ CH ２ CF ３ CF ２ CH (CH ３ ) ２ , CF(CH ３ )-CH(CH ３ ) ２ ), R ８ - Aryl (for example, CH ２ -Ph), C(=CH ２ )-R １０ (For example, C (=CH ２ )-C(O)-OCH ３ , C (=CH ２ )-CN), substituted or unsubstituted alkyl sulfones (e.g., SO ２ -CH ２ -Cyclopropyl), substituted or unsubstituted aryls (e.g., phenyl), substituted or unsubstituted heteroaryls (e.g., pyridines (2,3, and 4-pyridines); X １ is O, NH, or N-R ５０ And; R ８ is [CH ２ ] ｐ And; Here, p is between 1 and 10; R １０ H, CN, C １ -C ５ Linear or branched alkyl groups (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH) ３ )) or S(O) ２ It is R; R ５０ H, C １ -C ５ The linear or branched alkyl (e.g., methyl, ethyl, butyl, i-propyl) is either substituted or unsubstituted; R is C １ -C ５ Linear or branched alkyl groups, C １ -C ５ The linear or branched alkoxy, phenyl, aryl, or heteroaryl compounds, or two geminal R substituents bond together to form a 5- or 6-membered heterocyclic ring; Ring A is either absent or a 3- to 8-membered substituted or unsubstituted cycloalkyl ring (e.g., cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl); The B ring is either absent or a 3- to 8-membered substituted or unsubstituted saturated or unsaturated carbocyclic ring (e.g., cyclohexyl, cyclohexenyl, cyclopentyl); The C ring is either absent or a 3- to 8-membered substituted or unsubstituted cycloalkyl ring (e.g., cyclopropyl). Compounds represented by the structure shown, or their pesticide-acceptable salts, amphotericions (internal salts), stereoisomers, tautomers, hydrates, N-oxides, reverse amide analogs, isotopic variants (e.g., deuterated analogs), or any combination thereof; Here, R ３ and R ４ One of them is NH ２ And the other is OH.

3. Formula I: 【Transformation 3】 [During the ceremony, C Ｉ , C ＩＩ , C ＩＩＩ and C ＩＶ Depending on whether they are part of a triple bond, a double bond, or a single bond, they are independently sp carbon atoms, sp ２ carbon atoms or sp ３ It is a carbon atom; and each is a sp carbon atom; sp ２ carbon atom; or sp ３ For each carbon atom, independently, C;CH or C(R) ２０ ); or CH ２ CH(R ２０ ) or C (R ２０ ) ２ And; Here, R ２０ is a halogen (e.g., F) or C １ -C ５ A linear or branched alkyl group (e.g., methyl); C Ｉ ...C ＩＩ , C ＩＩ ...C ＩＩＩ , C ＩＩＩ ...C ＩＶ Each of these is independently either a single bond or a double bond, where C Ｉ ...C ＩＩ , C ＩＩ ...C ＩＩＩ and C ＩＩＩ ...C ＩＶ At least one of them is a double bond; or C Ｉ ...C ＩＩ , C ＩＩ ...C ＩＩＩ and C ＩＩＩ ...C ＩＶ Each of these is independently a single bond or a triple bond, where C Ｉ ...C ＩＩ , C ＩＩ ...C ＩＩＩ and C ＩＩＩ ...C ＩＶ At least one of them is a triple bond; R １ H, F, Cl, Br, I, C １ -C ５ The linear or branched alkyl groups (e.g., methyl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl, benzyl); Here, C Ｉ ...C ＩＩ If R is a triple bond, １ It does not exist; R ２ F, Cl, Br, I, C １ -C ５ Linear or branched substituted or unsubstituted alkyl groups (e.g., methyl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl), C ２ -C ５ A linear or branched substituted or unsubstituted alkenyl (e.g., etenyl (CH=CH)) ２ )), C ２ -C ５ The linear or branched substituted or unsubstituted alkynyl (e.g., ethynyl (CCH)); Or, R １ and R ２ They bond to form a 3-8 member substituted or unsubstituted saturated or unsaturated carbocyclic ring B (e.g., cyclohexyl, cyclohexenyl, cyclopentyl); R ２ ' is H, F, Cl, Br, I, C １ -C ５ Linear or branched substituted or unsubstituted alkyl groups (e.g., methyl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl), C ２ -C ５ A linear or branched substituted or unsubstituted alkenyl (e.g., etenyl (CH=CH)) ２ )), C ２ -C ５ The linear or branched substituted or unsubstituted alkynyl (e.g., ethynyl (CCH)); R ３ H, F, Cl, Br, I, OH, SH, NH ２ NHR, N(R) ２ And; Or, R ３ and R ２ ' is bonded to form a 3- to 8-membered substituted or unsubstituted cycloalkyl ring C (e.g., cyclopropyl); R ４ H, F, Cl, Br, I, OH, SH, NH ２ NHR, N(R) ２ And; R ４０ H, C １ -C ５ The linear or branched alkyl groups (e.g., methyl, ethyl, propyl, isopropyl, t-Bu, isobutyl, pentyl); Or, R ３ and R ４０ They bond together to form a 3- to 8-membered substituted or unsubstituted cycloalkyl ring A (e.g., cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl); R ５ H, C ２ -C ５ Linear or branched substituted or unsubstituted alkenyls, C ２ -C ５ Linear or branched substituted or unsubstituted alkynyl molecules (e.g., CCH, CH) ２ -CCH,), C １ -C ５ Linear or branched haloalkyl groups (e.g., CF ３ CF ２ CH ３ ,CH ２ CF ３ CF ２ CH ２ CH ３ ,CH ２ CH ２ CF ３ CF ２ CH (CH ３ ) ２ , CF(CH ３ )-CH(CH ３ ) ２ ), R ８ - Aryl (for example, CH ２ -Ph), C(=CH ２ )-R １０ (For example, C (=CH ２ )-C(O)-OCH ３ , C (=CH ２ )-CN), substituted or unsubstituted alkyl sulfones (e.g., SO ２ -CH ２ -Cyclopropyl), 0-substituted or unsubstituted aryls (e.g., phenyl), substituted or unsubstituted heteroaryls (e.g., pyridines (2,3, and 4-pyridines); X １ is O, NH, or N-R ５０ And; R ８ is [CH ２ ] ｐ And; Here, p is between 1 and 10; R １０ H, CN, C １ -C ５ Linear or branched alkyl groups (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH) ３ )) or S(O) ２ It is R; R ５０ H, C １ -C ５ The linear or branched alkyl (e.g., methyl, ethyl, butyl, i-propyl) is either substituted or unsubstituted; R is C １ -C ５ Linear or branched alkyl groups, C １ -C ５ The linear or branched alkoxy, phenyl, aryl, or heteroaryl compounds, or two geminal R substituents bond together to form a 5- or 6-membered heterocyclic ring; Ring A is either absent or a 3- to 8-membered substituted or unsubstituted cycloalkyl ring (e.g., cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl); The B ring is either absent or a 3- to 8-membered substituted or unsubstituted saturated or unsaturated carbocyclic ring (e.g., cyclohexyl, cyclohexenyl, cyclopentyl); The C ring is either absent or a 3- to 8-membered substituted or unsubstituted cycloalkyl ring (e.g., cyclopropyl). Compounds represented by the structure shown, or their pesticide-acceptable salts, amphotericions (internal salts), stereoisomers, tautomers, hydrates, N-oxides, reverse amide analogs, isotopic variants (e.g., deuterated analogs), or any combination thereof; Here, R ３ and R ４ At least one of them is NH ２ That is the case.

4. Formula II(a) - Formula II(d) or Formula III(a) - Formula III(c): 【Chemistry 4】 【change】 [In the formula, R', R'', and R'''' are each independently a halogen (e.g., F) or C １ -C ５ Selected from linear or branched alkyl groups (e.g., methyl groups). A compound according to any one of claims 1 to 3, represented by the structure.

5. R ２０ The compound according to any one of claims 1 to 3, wherein the compound is F or methyl.

6. R １ H is H, and R ２ ga CH ３ Or CH ２ CH ３ And, or, R １ and R ２ The compound according to any one of claims 1 to 3, wherein the compounds are bonded to form a cyclohexyl.

7. R ２ ' is H or CH ３ And, R ３ is H, OH, or NH ２ And, or, R ３ and R ２ The compound according to any one of claims 1 to 3, wherein ' is bonded to form a cyclopropyl group.

8. R ４ However, H or NH ２ The compound according to any one of claims 1 to 3.

9. R ４０ H is H, and R ３ is H, OH, or NH ２ And, or, R ３ and R ４０ The compound according to any one of claims 1 to 3, wherein the atoms are bonded to form a 3- to 8-membered cycloalkyl ring.

10. X １ A compound according to any one of claims 1 to 3, wherein is O.

11. R ５ The compound according to claim 1, wherein is H.

12. The compound according to any one of claims 1 to 3, wherein the compound is substantially a single, pure stereoisomer.

13. The compound according to claim 12, wherein the compound is substantially a pure SR stereoisomer, RS stereoisomer, RR stereoisomer, or SS diastereomer.

14. The compound according to claim 13, wherein the substantially pure stereoisomer has a purity of more than 90%, preferably more than 95%, and most preferably more than 98%.

15. A compound according to any one of claims 1 to 3, represented by any one of the following structures: Table 1

16. The compound according to claim 2 or 3, represented by any one of the following structures: Table 2

17. The compound according to claim 3, represented by any one of the following structures: Table 3

18. The compound according to any one of claims 1 to 3, wherein the compound is a herbicide, a pesticide, or a combination thereof.

19. A compound according to any one of claims 1 to 3, for use in controlling undesirable plant growth.

20. A pesticide composition comprising the compound described in any one of claims 1 to 3 and a pesticide-acceptable carrier or diluent.

21. The compound according to claim 19, wherein the plant is a true dicotyledonous plant (dicot) or a monocotyledonous plant (monocot).

22. The compound according to claim 19, wherein the plant is a weed.

23. The aforementioned weeds include Abutilon theophrasti, Amaranthus palmeri, Ambrosia artemisiifolia, Alopecurus myosuroides, Avena sterilis, Chenopodium album, Conyza canadensis, Digitaria sanguinalis, Echinochloa colona, ​​and Euphorbia. The compound according to claim 22, comprising heterophylla, rye (Lolium perenne), rye (Lolium rigidum), chamomile (Matricaria chamomilla), phalaris paradoxa, annual bluegrass (Poa annua), purslane (Portulaca oleracea), foxtail grass (Setaria viridis), black nightshade (Solanum nigrum), or any combination thereof.

24. The compound according to claim 21, wherein the dicotyledonous plant is Arabidopsis thaliana, and / or the monocotyledonous plant is Dactyloctenium aegyptium or Eragrostis teff.

25. The compound according to claim 19 for use in pre-planting treatment, pre-emergence treatment, post-emergence treatment, or any combination thereof.

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