PESTICIDAL AND HERBICIDAL COMPOUNDS AND METHODS OF USE THEREOF

FIELD OF THE INVENTION

The present invention relates to novel pesticidally and/or herbicidally active compounds, agrochemical composition thereof, methods of preparation thereof, and uses thereof for controlling the growth of undesirable plants (e.g., weeds), for example in crop fields.

BACKGROUND OF THE INVENTION

Weeds often interfere with efficient utilization of land and water resources and typically compete with desired plants for water, nutrients, light, carbon dioxide, and space. Many weeds are also aesthetically displeasing, especially when the weeds appear within a stand of a desired plant, such as St. Augustine grass or Kentucky bluegrass in a homeowner's lawn. Weeds may also obstruct visibility, become fire hazards around buildings, and reduce the efficiency of irrigation systems. When weeds appear in watercourses, such as rivers and lakes, the weeds may contribute to poor water quality, making the water unsuitable for culinary and industrial uses. Furthermore, some weeds act in a poisonous fashion against other plants, animals, and humans by secreting toxic substances known as alleopathic compounds or by spreading agents that may cause allergies and/or disease. Finally, weeds provide shelter for insects and rodents that spread disease or are otherwise harmful to desired plants, animals, or humans.

Weeds cause agricultural losses to crops that consistently exceed losses caused by other classes of agricultural pests, year after year. Besides reducing the quality of the crop, weed infestation may reduce achievable crop yield by up to 100% of the theoretically achievable yield. A number of approaches, including mechanical, agricultural, biological, and chemical techniques, have evolved in an attempt to control weed infestation.

Mechanical means, such as hand pulling, hoeing or cultivation, deep plowing, clipping, mowing, burning and/or mulching, may be employed in an attempt to eradicate or control weeds. Also, cover crops may be planted to keep the ground covered when not growing more valuable crops and thus weed infestation that would ordinarily be expected to occur in bare ground areas is typically minimized. Crop rotation and planting of “smother” crops that are adapted to grow more vigorously than weeds have also been attempted as means of controlling weed infestations. Besides these mechanical and agricultural techniques, biological methods of weed control, such as introduction of predator populations that feed on the weeds and thereby reduce weed population, have also been attempted.

Mechanical, agricultural, and biological methods of weed control, while sometimes helping to reduce the extent of weed infestations, are not fully satisfactory. First, mechanical and agricultural techniques are quite labor intensive and require use of limited physical and capital resources. Furthermore, environmental factors beyond the control of the farmer or homeowner, such as excessive rainfall, may diminish the effectiveness of these mechanical and agricultural techniques. Likewise, biological techniques, such as introduction of predator populations, are not entirely satisfactory, since the predators may not be selective for only the weed population.

Chemically active herbicides represent another potential weed control technique. These chemical herbicides may be broken down into pre-emergent herbicides and post-emergent herbicides. Pre-emergent herbicides typically interfere with germination of weed seeds, whereas post-emergent herbicides kill the weeds after the weed seeds have germinated and weed growth has begun.

Pre-emergent herbicides may be effective when present at the required dosage at the time weed seed germination is ready to occur. However, this timing issue points out a major problem with respect to pre-emergent herbicides. Specifically, if the pre-emergent herbicide is not applied, or degrades, prior to weed seed germination, the weed seeds are free to germinate and begin growing into mature weeds. Additionally, pre-emergent herbicides are typically weed specific and are not equally effective against all types of weeds. The timing problem present with pre-emergent herbicides may be avoided by employing post-emergent herbicides and by applying the post-emergent herbicide only after the weed seeds have germinated and the weeds are actively growing. However, many presently available post-emergent herbicides are non-selective herbicides and therefore will kill desirable plants in addition to weeds.

Many pre- and post-emergent herbicides also suffer from another problem. Specifically, many pre-emergent herbicides and post-emergent herbicides are either moderately or highly toxic to humans and animals, and may thereby have damaging effects far beyond the intended weed control effect. Toxic herbicides may cause injury either immediately or over the long term to persons applying the herbicides and to persons present when the herbicides are applied. Also, residual concentrations of toxic herbicides that remain in the soil or water after application of the herbicide may pose a significant threat to human beings and to animals, including land-based animals and amphibians and fish, upon contact with the treated area or runoff from the treated area. Furthermore, public alarm about the use of toxic chemicals as herbicides and their potential widespread and long-term effects on environmental quality dictate against the continued use of these toxic herbicides.

There is a need for a pesticidal and/or herbicidal solution that avoids the critical timing issues of pre-emergent herbicide applications. Furthermore, there is a need for a pesticidal and/or herbicidal solution that avoids the toxic effects of presently available pre-emergent and post-emergent herbicides on human beings, animals and the environment generally. Furthermore, there is a need for an economically efficient post-emergent 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 herbicides necessary to obtain sufficient weed control while minimizing the harm to crop plants.

As more weeds become resistant to herbicides, alternative compositions with high weed control are desired. Further, as no-till farming continues to increase in popularity, there is a greater need for effective herbicides. A composition with effective weed control and lower dosage rate will lead to increased crop plant yields, and decreased environmental, human, and mammalian health concerns.

SUMMARY OF THE INVENTION

In various embodiments, this invention is directed to a compound represented by the structure of formula I(d), I(e), or any one of the compounds as defined in Table 2 hereinbelow, or its agrochemically acceptable salt, zwitterion (inner salt), stereoisomer, tautomer, hydrate, N-oxide, reverse amide analog, isotopic variant (e.g., deuterated analog), or any combination thereof.

In various embodiments, this invention is directed to a pesticidal or an herbicidal compound represented by the structure of formula I-I(e), as defined herein below or its agrochemically acceptable salt, zwitterion (inner salt), stereoisomer, tautomer, hydrate, N-oxide, reverse amide analog, isotopic variant (e.g., deuterated analog), or any combination thereof.

In various embodiments, this invention is directed to a method for controlling the growth of undesired plants, comprising applying a compound represented by the structure of formula I-I(e), or its agrochemically acceptable salt, zwitterion (inner salt), stereoisomer, tautomer, hydrate, N-oxide, reverse amide analog, isotopic variant (e.g., deuterated analog), as defined herein below, or an agrochemical composition thereof, to a crop field.

In some embodiments, this invention is directed to a compound represented by any one of the compounds presented in Tables 1 and/or 2 herein below, or its agrochemically acceptable salt, zwitterion (inner salt), stereoisomer, tautomer, hydrate, N-oxide, reverse amide analog, isotopic variant, or any combination thereof. In various embodiments, the compound is not: 6-(2-aminopropoxy)picolinic acid; 6-(2-aminopropoxy)pyrazine-2-carboxylic acid, 2-(2-aminopropoxy)pyrimidine-4-carboxylic acid; 6-(2-aminopropoxy)-3-fluoropicolinic acid; 6-(2-aminopropoxy)-4-fluoropicolinic acid; 6-(2-aminobutoxy)picolinic acid; 6-((2-aminocyclopentyl)oxy)picolinic acid; methyl 6-(2-aminopropoxy)picolinate; or ethyl 6-(2-aminopropoxy)picolinate.

In various embodiments, the compound is a substantially pure single stereoisomer. In various embodiments, the compound is a substantially pure single enantiomer. In various embodiments, the compound is a mixture of stereoisomers. In various embodiments, the substantially pure stereoisomer or enantiomer has a purity higher than 90%, preferably higher than 95%, most preferably higher than 98%. In various embodiments, the compound is an herbicide or a pesticide (i.e., herbicidal or pesticidal compound).

In various embodiments, this invention is directed to an agrochemical composition comprising a pesticidally and/or herbicidally effective amount of a compound according to this invention, and an agrochemically-acceptable diluent or carrier. In various embodiments, the compound is for use in controlling the growth of undesired plants. In various embodiments, the compound is a substantially pure single stereoisomer, a mixture of stereoisomers, or a racemate. In various embodiments, the stereoisomer is an enantiomer. In various embodiments, the substantial pure stereoisomer has a purity higher than 90%, preferably higher than 95%, most preferably higher than 98%.

In various embodiments, this invention is directed to a method of controlling the growth of undesired plants, comprising applying a compound according to this invention or an agrochemical composition according to this invention, to crop fields.

In various embodiments, this invention is directed to a compound according to this invention, or an agrochemical composition according to this invention, for use in controlling the growth of undesired plants. In some embodiments, the plant is a eudicot (dicot) or a monocotyledon (monocot). In some embodiments, the plant is a weed. In some embodiments, the weed comprises: 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 dicot plant is Arabidopsis thaliana, and/or the monocot plant is Dactyloctenium aegyptium or Eragrostis teff. In some embodiments, the compound is for use in pre-plant treatments, pre-emergence treatments, post-emergence treatments, or any combination thereof; each represents a separate embodiment according to this invention.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 depicts the NMR spectrum of compound 116.

FIG. 2 depicts the NMR spectrum of compound 106.

DETAILED DESCRIPTION OF THE INVENTION

In various embodiments, this invention is directed to a compound represented by the structure of formula (I):

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wherein

- A and B rings are absent, or are each independently a substituted or unsubstituted aromatic or heteroaromatic ring system (e.g., B: aryl, pyridine), or a substituted or unsubstituted C₃-C₁₀cycloalkyl (A: cyclopropyl, B: cyclopentyl, cyclohexyl), or a substituted or unsubstituted C₃-C₁₀heterocyclic ring (e.g., pyrrolidine);
- R₁is H, substituted or unsubstituted C₁-C₁₀linear or branched, or C₃-C₈cyclic alkyl (e.g., methyl, ethyl, propyl, butyl, CH₂—CCH, CH₂—COOH, CH₂CH₂COOH), C(O)—R₁₀(e.g., C(O)—CH₃), R₈—OH (e.g., CH₂—OH), R₈—COO—R₁₀(e.g., CH₂—COOH, CH₂—COO—CH₃, CH₂—COO—CH₂CH₃, CH₂—CH₂—COOH, CH₂—CH₂—COO—CH₃, CH₂—CH₂—COO—CH₂CH₃), R₈—SH, —R₈—O—R₁₀, (e.g., —CH₂—O—CH₃), R₈—(C₃-C₈cycloalkyl), R₈-(3-8 membered heterocyclic ring), CF₃, NH₂, NHR, N(R)₂, R₈—N(R₁₀)(R₁₁), C(O)H, C₁-C₈linear or branched C(O)-haloalkyl (e.g., C(O)—CF₃), —C(O)NH₂, C(O)NHR, C(O)N(R₁₀)(R₁₁), C₂-C₅linear or branched, substituted or unsubstituted alkenyl (e.g., CH═C(Ph)₂), C₁-C₅linear or branched or C₃-C₈cyclic haloalkyl, substituted or unsubstituted 3-8 membered heterocyclic ring, substituted or unsubstituted aryl (e.g., phenyl), or substituted or unsubstituted benzyl
- R₂is H, substituted or unsubstituted C₁-C₁₀linear or branched, or C₃-C₈cyclic alkyl (e.g., methyl, ethyl, propyl, CH₂—CCH), F, Cl, Br, I, OH, SH, R₈—OH (e.g., CH₂—OH), R₈—SH, —R₈—O—R₁₀, (e.g., —CH₂—O—CH₃), R₈—(C₃-C₈cycloalkyl), R₈-(3-8 membered heterocyclic ring), CF₃, CN, NO₂, R₈—N(R₁₀)(R₁₁), C(O)H, C₁-C₈linear or branched C(O)-haloalkyl (e.g., C(O)—CF₃), —C(O)NH₂, C(O)NHR, C(O)N(R₁₀)(R₁₁), C₂-C₈linear or branched, substituted or unsubstituted alkenyl (e.g., CH═C(Ph)₂), C₁-C₈linear or branched or C₃-C₈cyclic haloalkyl, substituted or unsubstituted 3-8 membered heterocyclic ring, substituted or unsubstituted aryl (e.g., phenyl), or substituted or unsubstituted benzyl
- R₃is H, substituted or unsubstituted C₁-C₁₀linear or branched, or C₃-C₈cyclic alkyl (e.g., methyl, ethyl, propyl, CH₂—CCH, C(H)(OH)(CH₃)), F, Cl, Br, I, OH, SH, R₈—OH (e.g., CH₂—OH), R₈—SH, —R₈—O—R₁₀, (e.g., —CH₂—O—CH₃), R₈—(C₃-C₈cycloalkyl), R₈-(3-8 membered heterocyclic ring), CF₃, CN, NO₂, NH₂, NHR, N(R)₂, R₈—N(R₁₀)(R₁₁) (e.g. CH₂—NH₂); C(O)H, C₁-C₈linear or branched C(O)-haloalkyl (e.g., C(O)—CF₃), —C(O)NH₂, C(O)NHR, C(O)N(R₁₀)(R₁₁), C₂-C₈linear or branched, substituted or unsubstituted alkenyl (e.g., CH═C(Ph)₂), C₁-C₈linear or branched or C₃-C₈cyclic haloalkyl, substituted or unsubstituted 3-8 membered heterocyclic ring, substituted or unsubstituted aryl (e.g., phenyl), or substituted or unsubstituted benzyl
- or R₂and R₃are joined to form a C₃-C₈substituted or unsubstituted, saturated or unsaturated, aliphatic (e.g. cyclopentyl, cyclohexyl), or aromatic (e.g. pyridine), carbocyclic or heterocyclic ring (e.g. pyrrolidine);
- R₄is H, substituted or unsubstituted C₁-C₁₀linear or branched, or C₃-C₈cyclic alkyl (e.g., methyl, ethyl, propyl, CH₂—CCH), F, Cl, Br, I, OH, SH, R₈—OH (e.g., CH₂—OH), R₈—SH, —R₈—O—R₁₀, (e.g., —CH₂—O—CH₃), R₈—(C₃-C₈cycloalkyl), R₈-(3-8 membered heterocyclic ring), CF₃, CN, NO₂, NH₂, NHR, N(R)₂, R₈—N(R₁₀)(R₁₁) (e.g. CH₂—NH₂), C(O)H, C₁-C₈linear or branched C(O)-haloalkyl (e.g., C(O)—CF₃), —C(O)NH₂, C(O)NHR, C(O)N(R₁₀)(R₁₁), C₂-C₈linear or branched, substituted or unsubstituted alkenyl (e.g., CH═C(Ph)₂), C₁-C₈linear or branched or C₃-C₈cyclic haloalkyl, substituted or unsubstituted 3-8 membered heterocyclic ring, substituted or unsubstituted aryl (e.g., phenyl), or substituted or unsubstituted benzyl
- or R₃and R₄are joined to form a substituted or unsubstituted, saturated or unsaturated, aliphatic or aromatic, carbocyclic or heterocyclic 3-8 membered ring (e.g. cyclopropyl), C═O or ═N—OH;
- R₅is H, OH, SH, NH₂, NHNH₂, NHR, N(R₁₀)(R₁₁) (e.g., N(H)CH₃, N(H)CH₂CH₃), R₈—N(R₁₀)(R₁₁) (e.g. CH₂—NH₂); or R₂and R₅are joined to form a substituted or unsubstituted 4-8 membered heterocyclic ring (e.g. pyrrolidine);
- R₆and R₆₀are each independently H, F, Cl, Br, I, OH, SH, R₈—OH (e.g., CH₂—OH), R₈—SH, —R₈—O—R₁₀, (e.g., —CH₂—O—CH₃), R₈—(C₃-C₈cycloalkyl), R₈-(3-8 membered heterocyclic ring), CF₃, CD₃, OCD₃, CN, NO₂, —CH₂CN, —R₈CN, NH₂, NHR, N(R)₂, R₈—N(R₁₀)(R₁₁), R₉—R₈—N(R₁₀)(R₁₁), B(OH)₂, —OC(O)CF₃, —OCH₂Ph, NHC(O)—R₁₀(e.g., NHC(O)CH₃), NHC(O)—N(R₁₀)(R₁₁) (e.g., NHC(O)N(CH₃)₂), COOH, —C(O)Ph, C(O)O—R₁₀(e.g. C(O)O—CH₃), R₈—C(O)—R₁₀(e.g., CH₂C(O)CH₃), C(O)H, C(O)—R₁₀(e.g., C(O)—CH₃, C(O)—CH₂CH₃, C(O)—CH₂CH₂CH₃), C₁-C₈linear or branched C(O)-haloalkyl (e.g., C(O)—CF₃), —C(O)NH₂, C(O)NHR, C(O)N(R₁₀)(R₁₁) (e.g., C(O)N(CH₃)₂), SO₂R, SO₂N(R₁₀)(R₁₁) (e.g., SO₂N(CH₃)₂, SO₂NHC(O)CH₃), C₁-C₈linear or branched, substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl, benzyl), substituted or unsubstituted C₃-C₈cycloalkyl (e.g., cyclopropyl, cyclopentyl), C₂-C₈linear or branched, substituted or unsubstituted alkenyl (e.g., ethenyl), C₂-C₈linear or branched, substituted or unsubstituted alkynyl (e.g., ethynyl, CC—CH₂-cyclobutyl, CC—CF₃), C₁-C₈linear or branched or C₃-C₈cyclic haloalkyl (e.g., CF₃, CF₂CH₃, CH₂CF₃, CF₂CH₂CH₃, CH₂CH₂CF₃, CF₂CH(CH₃)₂, CF(CH₃)—CH(CH₃)₂), substituted or unsubstituted C₁-C₈linear or branched or C₃-C₈cyclic alkoxy (e.g. methoxy, ethoxy, propoxy, isopropoxy, O—CH₂—CF₃), optionally wherein at least one methylene group (CH₂) in the alkoxy is replaced with an oxygen atom, C₁-C₈linear or branched thioalkoxy, C₁-C₈linear or branched haloalkoxy (e.g., OCF₃, OCHF₂), substituted or unsubstituted 3-8 membered heterocyclic ring (e.g., thiophene, oxazole, oxadiazole, imidazole, furane, triazole, tetrazole, pyridine, pyrimidine, pyrazine), substituted or unsubstituted aryl (e.g., phenyl), substituted or unsubstituted benzyl;
- X₁is O, S, NH, NR (e.g., N—CH₃), S═O, SO₂; or X₁and R₄are joined to form a 4-8 membered heterocyclic ring (e.g., pyrrolidine);
- X₂, X₃, X₄, X₅are each independently C or N;
- X₆is O, NH, NR or CH₂;
- G=X is C═O or SO₂or G(═X)—X₆—R₁is a tetrazole moiety;
- R₈is [CH₂]p
  - wherein p is between 1 and 10;
- R₉is [CH]_q, [C]_q
  - wherein q is between 2 and 10;
- R₁₀and R₁₁are each independently H, CN, C₁-C₈linear or branched alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH₃)), or S(O)₂R;
- or R₁₀and R₁₁are joined to form a substituted or unsubstituted 3-8 membered heterocyclic ring,
- R is H, C₁-C₈linear or branched alkyl (e.g., methyl, ethyl), C₁-C₈linear or branched alkoxy (e.g., methoxy), phenyl, aryl or heteroaryl, or two gem R substituents are joined together to form a 5 or 6 membered heterocyclic ring;
- k is an integer number between 1 and 3 (e.g., 1, 2);
  
  or agrochemically acceptable salt, zwitterion (inner salt), stereoisomer, tautomer, hydrate, N-oxide, reverse amide analog, isotopic variant (e.g., deuterated analog), or any combination thereof.

In various embodiments, if k is not 1, then R₂is H. In various embodiments, if k is 2, then R₂is H. In various embodiments, if k is 3, then R₂is H.

In various embodiments, the term “substituted” refers to substituted with at least one substitution selected from: F, Cl, Br, I, C₁-C₈linear or branched alkyl, C₂-C₈linear or branched alkenyl (e.g., ethenyl), C₂-C₈linear or branched alkynyl, alkyl amide (i.e., C(O)NH—R or NHC(O)—R), alkyl ester (i.e., COOR or OC(O)—R), OH, alkoxy, N(R)₂, NH₂, CF₃, aryl, phenyl, heteroaryl, C₃-C₈cycloalkyl, halophenyl, CN and NO₂.

In various embodiments, this invention is directed to a compound represented by the structure of formula I(a):

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wherein

- A and B rings are absent, or are each independently a substituted or unsubstituted aromatic or heteroaromatic ring system (e.g., B: aryl, pyridine), or a substituted or unsubstituted C₃-C₁₀cycloalkyl (A: cyclopropyl, B: cyclopentyl, cyclohexyl), or a substituted or unsubstituted 3-10 membered heterocyclic ring (e.g., pyrrolidine);
- R₁is H, substituted or unsubstituted C₁-C₁₀linear or branched, or C₃-C₈cyclic alkyl (e.g., methyl, ethyl, propyl, butyl, CH₂—CCH, CH₂—COOH, CH₂CH₂COOH), C(O)—R₁₀(e.g., C(O)—CH₃), R₈—OH (e.g., CH₂—OH), R₈—COO—R₁₀(e.g., CH₂—COOH, CH₂—COO—CH₃, CH₂—COO—CH₂CH₃, CH₂—CH₂—COOH, CH₂—CH₂—COO—CH₃, CH₂—CH₂—COO—CH₂CH₃), R₈—SH, —R₈—O—R₁₀, (e.g., —CH₂—O—CH₃), R₈—(C₃-C₈cycloalkyl), R₈-(3-8 membered heterocyclic ring), CF₃, NH₂, NHR, N(R)₂, R₈—N(R₁₀)(R₁₁), C(O)H, C₁-C₅linear or branched C(O)-haloalkyl (e.g., C(O)—CF₃), —C(O)NH₂, C(O)NHR, C(O)N(R₁₀)(R₁₁), C₂-C₅linear or branched, substituted or unsubstituted alkenyl (e.g., CH═C(Ph)₂), C₁-C₅linear or branched or C₃-C₈cyclic haloalkyl, substituted or unsubstituted 3-8 membered heterocyclic ring, substituted or unsubstituted aryl (e.g., phenyl), or substituted or unsubstituted benzyl;
- R₂is H, substituted or unsubstituted C₁-C₁₀linear or branched, or C₃-C₈cyclic alkyl (e.g., methyl, ethyl, propyl, CH₂—CCH), F, Cl, Br, I, OH, SH, R₈—OH (e.g., CH₂—OH), R₈—SH, —R₈—O—R₁₀, (e.g., —CH₂—O—CH₃), R₈—(C₃-C₈cycloalkyl), R₈-(3-8 membered heterocyclic ring), CF₃, CN, NO₂, R₈—N(R₁₀)(R₁₁), C(O)H, C₁-C₅linear or branched C(O)-haloalkyl (e.g., C(O)—CF₃), —C(O)NH₂, C(O)NHR, C(O)N(R₁₀)(R₁₁), C₂-C₅linear or branched, substituted or unsubstituted alkenyl (e.g., CH═C(Ph)₂), C₁-C₅linear or branched or C₃-C₈cyclic haloalkyl, substituted or unsubstituted 3-8 membered heterocyclic ring, substituted or unsubstituted aryl (e.g., phenyl), or substituted or unsubstituted benzyl;
- R₃is H, substituted or unsubstituted C₁-C₁₀linear or branched, or C₃-C₈cyclic alkyl (e.g., methyl, ethyl, propyl, CH₂—CCH, C(H)(OH)(CH₃)), F, Cl, Br, I, OH, SH, R₈—OH (e.g., CH₂—OH), R₈—SH, —R₈—O—R₁₀, (e.g., —CH₂—O—CH₃), R₈—(C₃-C₈cycloalkyl), R₈-(3-8 membered heterocyclic ring), CF₃, CN, NO₂, NH₂, NHR, N(R)₂, R₈—N(R₁₀)(R₁₁) (e.g. CH₂—NH₂); C(O)H, C₁-C₈linear or branched C(O)-haloalkyl (e.g., C(O)—CF₃), —C(O)NH₂, C(O)NHR, C(O)N(R₁₀)(R₁₁), C₂-C₈linear or branched, substituted or unsubstituted alkenyl (e.g., CH═C(Ph)₂), C₁-C₈linear or branched or C₃-C₈cyclic haloalkyl, substituted or unsubstituted 3-8 membered heterocyclic ring, substituted or unsubstituted aryl (e.g., phenyl), or substituted or unsubstituted benzyl;
- or R₂and R₃are joined to form a C₃-C₈substituted or unsubstituted, saturated or unsaturated, aliphatic (e.g. cyclopentyl, cyclohexyl), or aromatic (e.g. pyridine), carbocyclic or heterocyclic ring (e.g. pyrrolidine);
- R₄is H, substituted or unsubstituted C₁-C₁₀linear or branched, or C₃-C₈cyclic alkyl (e.g., methyl, ethyl, propyl, CH₂—CCH), F, Cl, Br, I, OH, SH, R₈—OH (e.g., CH₂—OH), R₈—SH, —R₈—O—R₁₀, (e.g., —CH₂—O—CH₃), R₈—(C₃-C₈cycloalkyl), R₈-(3-8 membered heterocyclic ring), CF₃, CN, NO₂, NH₂, NHR, N(R)₂, R₈—N(R₁₀)(R₁₁) (e.g. CH₂—NH₂), C(O)H, C₁-C₈linear or branched C(O)-haloalkyl (e.g., C(O)—CF₃), —C(O)NH₂, C(O)NHR, C(O)N(R₁₀)(R₁₁), C₂-C₈linear or branched, substituted or unsubstituted alkenyl (e.g., CH═C(Ph)₂), C₁-C₈linear or branched or C₃-C₈cyclic haloalkyl, substituted or unsubstituted 3-8 membered heterocyclic ring, substituted or unsubstituted aryl (e.g., phenyl), or substituted or unsubstituted benzyl;
- or R₃and R₄are joined to form a substituted or unsubstituted, saturated or unsaturated, aliphatic or aromatic, carbocyclic or heterocyclic 3-8 membered ring (e.g. cyclopropyl), C═O or ═N—OH;
- R₅is H, OH, SH, NH₂, NHNH₂, NHR, N(R₁₀)(R₁₁) (e.g., N(H)CH₃, N(H)CH₂CH₃), R₈—N(R₁₀)(R₁₁) (e.g. CH₂—NH₂); or R₂and R₅are joined to form a substituted or unsubstituted 4-8 membered heterocyclic ring (e.g. pyrrolidine);
- R₆₀is absent or is H, F, Cl, Br, I, OH, SH, R₈—OH (e.g., CH₂—OH), R₈—SH, —R₈—O—R₁₀, (e.g., —CH₂—O—CH₃), R₈—(C₃-C₈cycloalkyl), R₈-(3-8 membered heterocyclic ring), CF₃, CD₃, OCD₃, CN, NO₂, —CH₂CN, —R₈CN, NH₂, NHR, N(R)₂, R₈—N(R₁₀)(R₁₁), R₉—R₈—N(R₁₀)(R₁₁), B(OH)₂, —OC(O)CF₃, —OCH₂Ph, NHC(O)—R₁₀(e.g., NHC(O)CH₃), NHC(O)—N(R₁₀)(R₁₁) (e.g., NHC(O)N(CH₃)₂), COOH, —C(O)Ph, C(O)O—R₁₀(e.g. C(O)O—CH₃), R₈—C(O)—R₁₀(e.g., CH₂C(O)CH₃), C(O)H, C(O)—R₁₀(e.g., C(O)—CH₃, C(O)—CH₂CH₃, C(O)—CH₂CH₂CH₃), C₁-C₈linear or branched C(O)-haloalkyl (e.g., C(O)—CF₃), —C(O)NH₂, C(O)NHR, C(O)N(R₁₀)(R₁₁) (e.g., C(O)N(CH₃)₂), SO₂R, SO₂N(R₁₀)(R₁₁) (e.g., SO₂N(CH₃)₂, SO₂NHC(O)CH₃), C₁-C₈linear or branched, substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl, benzyl), substituted or unsubstituted C₃-C₈cycloalkyl (e.g., cyclopropyl, cyclopentyl), C₂-C₈linear or branched, substituted or unsubstituted alkenyl (e.g., ethenyl), C₂-C₈linear or branched, substituted or unsubstituted alkynyl (e.g., ethynyl, CC—CH₂-cyclobutyl, CC—CF₃), C₁-C₈linear or branched or C₃-C₈cyclic haloalkyl (e.g., CF₃, CF₂CH₃, CH₂CF₃, CF₂CH₂CH₃, CH₂CH₂CF₃, CF₂CH(CH₃)₂, CF(CH₃)—CH(CH₃)₂), substituted or unsubstituted C₁-C₈linear or branched or C₃-C₈cyclic alkoxy (e.g. methoxy, ethoxy, propoxy, isopropoxy, O—CH₂—CF₃), optionally wherein at least one methylene group (CH₂) in the alkoxy is replaced with an oxygen atom, C₁-C₈linear or branched thioalkoxy, C₁-C₈linear or branched haloalkoxy (e.g., OCF₃, OCHF₂), substituted or unsubstituted 3-8 membered heterocyclic ring (e.g., thiophene, oxazole, oxadiazole, imidazole, furane, triazole, tetrazole, pyridine, pyrimidine, pyrazine), substituted or unsubstituted aryl (e.g., phenyl), substituted or unsubstituted benzyl;
- R₇₀is absent or is H, F, Cl, Br, I, OH, SH, R₈—OH (e.g., CH₂—OH), R₈—SH, —R₈—O—R₁₀, (e.g., —CH₂—O—CH₃), R₈—(C₃-C₈cycloalkyl), R₈-(3-8 membered heterocyclic ring), CF₃, CD₃, OCD₃, CN, NO₂, —CH₂CN, —R₈CN, NH₂, NHR, N(R)₂, R₈—N(R₁₀)(R₁₁), R₉—R₈—N(R₁₀)(R₁₁), B(OH)₂, —OC(O)CF₃, —OCH₂Ph, NHC(O)—R₁₀(e.g., NHC(O)CH₃), NHC(O)—N(R₁₀)(R₁₁) (e.g., NHC(O)N(CH₃)₂), COOH, —C(O)Ph, C(O)O—R₁₀(e.g. C(O)O—CH₃), R₈—C(O)—R₁₀(e.g., CH₂C(O)CH₃), C(O)H, C(O)—R₁₀(e.g., C(O)—CH₃, C(O)—CH₂CH₃, C(O)—CH₂CH₂CH₃), C₁-C₈linear or branched C(O)-haloalkyl (e.g., C(O)—CF₃), —C(O)NH₂, C(O)NHR, C(O)N(R₁₀)(R₁₁) (e.g., C(O)N(CH₃)₂), SO₂R, SO₂N(R₁₀)(R₁₁) (e.g., SO₂N(CH₃)₂, SO₂NHC(O)CH₃), C₁-C₈linear or branched, substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl, benzyl), substituted or unsubstituted C₃-C₈cycloalkyl (e.g., cyclopropyl, cyclopentyl), C₂-C₈linear or branched, substituted or unsubstituted alkenyl (e.g., ethenyl), C₂-C₈linear or branched, substituted or unsubstituted alkynyl (e.g., ethynyl, CC—CH₂-cyclobutyl, CC—CF₃), C₁-C₈linear or branched or C₃-C₈cyclic haloalkyl (e.g., CF₃, CF₂CH₃, CH₂CF₃, CF₂CH₂CH₃, CH₂CH₂CF₃, CF₂CH(CH₃)₂, CF(CH₃)—CH(CH₃)₂), substituted or unsubstituted C₁-C₈linear or branched or C₃-C₈cyclic alkoxy (e.g. methoxy, ethoxy, propoxy, isopropoxy, O—CH₂—CF₃), optionally wherein at least one methylene group (CH₂) in the alkoxy is replaced with an oxygen atom, C₁-C₈linear or branched thioalkoxy, C₁-C₈linear or branched haloalkoxy (e.g., OCF₃, OCHF₂), substituted or unsubstituted 3-8 membered heterocyclic ring (e.g., thiophene, oxazole, oxadiazole, imidazole, furane, triazole, tetrazole, pyridine, pyrimidine, pyrazine), substituted or unsubstituted aryl (e.g., phenyl), substituted or unsubstituted benzyl;
- R₈₀is absent or is H, F, Cl, Br, I, OH, SH, R₈—OH (e.g., CH₂—OH), R₈—SH, —R₈—O—R₁₀, (e.g., —CH₂—O—CH₃), R₈—(C₃-C₈cycloalkyl), R₈-(3-8 membered heterocyclic ring), CF₃, CD₃, OCD₃, CN, NO₂, —CH₂CN, —R₈CN, NH₂, NHR, N(R)₂, R₈—N(R₁₀)(R₁₁), R₉—R₈—N(R₁₀)(R₁₁), B(OH)₂, —OC(O)CF₃, —OCH₂Ph, NHC(O)—R₁₀(e.g., NHC(O)CH₃), NHC(O)—N(R₁₀)(R₁₁) (e.g., NHC(O)N(CH₃)₂), COOH, —C(O)Ph, C(O)O—R₁₀(e.g. C(O)O—CH₃), R₈—C(O)—R₁₀(e.g., CH₂C(O)CH₃), C(O)H, C(O)—R₁₀(e.g., C(O)—CH₃, C(O)—CH₂CH₃, C(O)—CH₂CH₂CH₃), C₁-C₈linear or branched C(O)-haloalkyl (e.g., C(O)—CF₃), —C(O)NH₂, C(O)NHR, C(O)N(R₁₀)(R₁₁) (e.g., C(O)N(CH₃)₂), SO₂R, SO₂N(R₁₀)(R₁₁) (e.g., SO₂N(CH₃)₂, SO₂NHC(O)CH₃), C₁-C₈linear or branched, substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl, benzyl), substituted or unsubstituted C₃-C₈cycloalkyl (e.g., cyclopropyl, cyclopentyl), C₂-C₈linear or branched, substituted or unsubstituted alkenyl (e.g., ethenyl), C₂-C₈linear or branched, substituted or unsubstituted alkynyl (e.g., ethynyl, CC—CH₂-cyclobutyl, CC—CF₃), C₁-C₈linear or branched or C₃-C₈cyclic haloalkyl (e.g., CF₃, CF₂CH₃, CH₂CF₃, CF₂CH₂CH₃, CH₂CH₂CF₃, CF₂CH(CH₃)₂, CF(CH₃)—CH(CH₃)₂), substituted or unsubstituted C₁-C₈linear or branched or C₃-C₈cyclic alkoxy (e.g. methoxy, ethoxy, propoxy, isopropoxy, O—CH₂—CF₃), optionally wherein at least one methylene group (CH₂) in the alkoxy is replaced with an oxygen atom, C₁-C₈linear or branched thioalkoxy, C₁-C₈linear or branched haloalkoxy (e.g., OCF₃, OCHF₂), substituted or unsubstituted 3-8 membered heterocyclic ring (e.g., thiophene, oxazole, oxadiazole, imidazole, furane, triazole, tetrazole, pyridine, pyrimidine, pyrazine), substituted or unsubstituted aryl (e.g., phenyl), substituted or unsubstituted benzyl;
- R₉₀is absent or is H, F, Cl, Br, I, OH, SH, R₈—OH (e.g., CH₂—OH), R₈—SH, —R₈—O—R₁₀, (e.g., —CH₂—O—CH₃), R₈—(C₃-C₈cycloalkyl), R₈-(3-8 membered heterocyclic ring), CF₃, CD₃, OCD₃, CN, NO₂, —CH₂CN, —R₈CN, NH₂, NHR, N(R)₂, R₈—N(R₁₀)(R₁₁), R₉—R₈—N(R₁₀)(R₁₁), B(OH)₂, —OC(O)CF₃, —OCH₂Ph, NHC(O)—R₁₀(e.g., NHC(O)CH₃), NHC(O)—N(R₁₀)(R₁₁) (e.g., NHC(O)N(CH₃)₂), COOH, —C(O)Ph, C(O)O—R₁₀(e.g. C(O)O—CH₃), R₈—C(O)—R₁₀(e.g., CH₂C(O)CH₃), C(O)H, C(O)—R₁₀(e.g., C(O)—CH₃, C(O)—CH₂CH₃, C(O)—CH₂CH₂CH₃), C₁-C₈linear or branched C(O)-haloalkyl (e.g., C(O)—CF₃), —C(O)NH₂, C(O)NHR, C(O)N(R₁₀)(R₁₁) (e.g., C(O)N(CH₃)₂), SO₂R, SO₂N(R₁₀)(R₁₁) (e.g., SO₂N(CH₃)₂, SO₂NHC(O)CH₃), C₁-C₈linear or branched, substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl, benzyl), substituted or unsubstituted C₃-C₈cycloalkyl (e.g., cyclopropyl, cyclopentyl), C₂-C₈linear or branched, substituted or unsubstituted alkenyl (e.g., ethenyl), C₂-C₈linear or branched, substituted or unsubstituted alkynyl (e.g., ethynyl, CC—CH₂-cyclobutyl, CC—CF₃), C₁-C₈linear or branched or C₃-C₈cyclic haloalkyl (e.g., CF₃, CF₂CH₃, CH₂CF₃, CF₂CH₂CH₃, CH₂CH₂CF₃, CF₂CH(CH₃)₂, CF(CH₃)—CH(CH₃)₂), substituted or unsubstituted C₁-C₈linear or branched or C₃-C₈cyclic alkoxy (e.g. methoxy, ethoxy, propoxy, isopropoxy, O—CH₂—CF₃), optionally wherein at least one methylene group (CH₂) in the alkoxy is replaced with an oxygen atom, C₁-C₈linear or branched thioalkoxy, C₁-C₈linear or branched haloalkoxy (e.g., OCF₃, OCHF₂), substituted or unsubstituted 3-8 membered heterocyclic ring (e.g., thiophene, oxazole, oxadiazole, imidazole, furane, triazole, tetrazole, pyridine, pyrimidine, pyrazine), substituted or unsubstituted aryl (e.g., phenyl), substituted or unsubstituted benzyl;
- X₁is O, S, NH, NR (e.g., N—CH₃), S═O, SO₂; or X₁and R₄are joined to form a 4-8 membered heterocyclic ring (e.g., pyrrolidine);
- X₂, X₃, X₄, X₅are each independently C or N, wherein if any one of X₂-X₅is N then the respective R₆₀—R₉₀is absent;
- X₆is O, NH, NR or CH₂;
- G=X is C═O or SO₂or G(═X)—X₆—R₁is a tetrazole moiety;
- R₈is [CH₂]p
  - wherein p is between 1 and 10;
- R₉is [CH]_q, [C]_q
  - wherein q is between 2 and 10;
- R₁₀and R₁₁are each independently H, CN, C₁-C₈linear or branched alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH₃)), or S(O)₂R;
- or R₁₀and R₁₁are joined to form a substituted or unsubstituted 3-8 membered heterocyclic ring;
- R is H, C₁-C₈linear or branched alkyl (e.g., methyl, ethyl), C₁-C₈linear or branched alkoxy (e.g., methoxy), phenyl, aryl or heteroaryl, or two gem R substituents are joined together to form a 5 or 6 membered heterocyclic ring;
- k is an integer number between 1 and 3 (e.g., 1, 2);
- or agrochemically acceptable salt, zwitterion (inner salt), stereoisomer, tautomer, hydrate, N-oxide, reverse amide analog, isotopic variant (e.g., deuterated analog), or any combination thereof.

In various embodiments, if k is not 1, then R₂is H. In various embodiments, if k is 2, then R₂is H. In various embodiments, if k is 3, then R₂is H.

In various embodiments, this invention is directed to a compound represented by the structure of formula I(b):

embedded image

wherein

- C ring is a saturated or unsaturated aliphatic or heterocyclic 4-7 membered ring (e.g., cyclohexyl, cyclohexenyl, isoxazole, triazole, pyrazole, oxadiazole, furan, thiazole, pyrrole, thiophene);
  - or C is represented by the following structure:

embedded image

- - wherein X₂, X₃, X₄and X₅are each independently N or C, and
  - wherein at least one of X₂-X₅is N;
- A and B rings are absent, or are each independently a substituted or unsubstituted aromatic or heteroaromatic ring system (e.g., aryl, pyridine), or a substituted or unsubstituted C₃-C₁₀cycloalkyl (cyclopropyl, cyclopentyl, cyclohexyl), or a substituted or unsubstituted C₃-C₁₀heterocyclic ring (e.g., pyrrolidine);
- R₁is H, substituted or unsubstituted C₁-C₁₀linear or branched, or C₃-C₈cyclic alkyl (e.g., methyl, ethyl, propyl, butyl, CH₂—CCH, CH₂—COOH, CH₂CH₂COOH), C(O)—R₁₀(e.g., C(O)—CH₃), R₈—OH (e.g., CH₂—OH), R₈—COO—R₁₀(e.g., CH₂—COOH, CH₂—COO—CH₃, CH₂—COO—CH₂CH₃, CH₂—CH₂—COOH, CH₂—CH₂—COO—CH₃, CH₂—CH₂—COO—CH₂CH₃), R₈—SH, —R₈—O—R₁₀, (e.g., —CH₂—O—CH₃), R₈—(C₃-C₈cycloalkyl), R₈-(3-8 membered heterocyclic ring), CF₃, NH₂, NHR, N(R)₂, R₈—N(R₁₀)(Ru), C(O)H, C₁-C₈linear or branched C(O)-haloalkyl (e.g., C(O)—CF₃), —C(O)NH₂, C(O)NHR, C(O)N(R₁₀)(R₁₁), C₂-C₈linear or branched, substituted or unsubstituted alkenyl (e.g., CH═C(Ph)₂), C₁-C₈linear or branched or C₃-C₈cyclic haloalkyl, substituted or unsubstituted 3-8 membered heterocyclic ring, substituted or unsubstituted aryl (e.g., phenyl), or substituted or unsubstituted benzyl;
- R₂is H, substituted or unsubstituted C₁-C₁₀linear or branched, or C₃-C₈cyclic alkyl (e.g., methyl, ethyl, propyl, CH₂—CCH), F, Cl, Br, I, OH, SH, R₈—OH (e.g., CH₂—OH), R₈—SH, —R₈—O—R₁₀, (e.g., —CH₂—O—CH₃), R₈—(C₃-C₈cycloalkyl), R₈-(3-8 membered heterocyclic ring), CF₃, CN, NO₂, R₈—N(R₁₀)(R₁₁), C(O)H, C₁-C₈linear or branched C(O)-haloalkyl (e.g., C(O)—CF₃), —C(O)NH₂, C(O)NHR, C(O)N(R₁₀)(R₁₁), C₂-C₈linear or branched, substituted or unsubstituted alkenyl (e.g., CH═C(Ph)₂), C₁-C₅linear or branched or C₃-C₈cyclic haloalkyl, substituted or unsubstituted 3-8 membered heterocyclic ring, substituted or unsubstituted aryl (e.g., phenyl), or substituted or unsubstituted benzyl;
- R₃is H, substituted or unsubstituted C₁-C₁₀linear or branched, or C₃-C₈cyclic alkyl (e.g., methyl, ethyl, propyl, CH₂—CCH, C(H)(OH)(CH₃)), F, Cl, Br, I, OH, SH, R₈—OH (e.g., CH₂—OH), R₈—SH, —R₈—O—R₁₀, (e.g., —CH₂—O—CH₃), R₈—(C₃-C₈cycloalkyl), R₈-(3-8 membered heterocyclic ring), CF₃, CN, NO₂, NH₂, NHR, N(R)₂, R₈—N(R₁₀)(R₁₁) (e.g. CH₂—NH₂); C(O)H, C₁-C₈linear or branched C(O)-haloalkyl (e.g., C(O)—CF₃), —C(O)NH₂, C(O)NHR, C(O)N(R₁₀)(R₁₁), C₂-C₈linear or branched, substituted or unsubstituted alkenyl (e.g., CH═C(Ph)₂), C₁-C₈linear or branched or C₃-C₈cyclic haloalkyl, substituted or unsubstituted 3-8 membered heterocyclic ring, substituted or unsubstituted aryl (e.g., phenyl), or substituted or unsubstituted benzyl;
- or R₂and R₃are joined to form a C₃-C₈substituted or unsubstituted, saturated or unsaturated, aliphatic (e.g. cyclopentyl, cyclohexyl), or aromatic (e.g. pyridine), carbocyclic or heterocyclic ring (e.g. pyrrolidine);
- R₄is H, substituted or unsubstituted C₁-C₁₀linear or branched, or C₃-C₈cyclic alkyl (e.g., methyl, ethyl, propyl, CH₂—CCH), F, Cl, Br, I, OH, SH, R₈—OH (e.g., CH₂—OH), R₈—SH, —R₈—O—R₁₀, (e.g., —CH₂—O—CH₃), R₈—(C₃-C₈cycloalkyl), R₈-(3-8 membered heterocyclic ring), CF₃, CN, NO₂, NH₂, NHR, N(R)₂, R₈—N(R₁₀)(R₁₁) (e.g. CH₂—NH₂), C(O)H, C₁-C₈linear or branched C(O)-haloalkyl (e.g., C(O)—CF₃), —C(O)NH₂, C(O)NHR, C(O)N(R₁₀)(Ru), C₂-C₈linear or branched, substituted or unsubstituted alkenyl (e.g., CH═C(Ph)₂), C₁-C₈linear or branched or C₃-C₈cyclic haloalkyl, substituted or unsubstituted 3-8 membered heterocyclic ring, substituted or unsubstituted aryl (e.g., phenyl), or substituted or unsubstituted benzyl;
- or R₃and R₄are joined to form a substituted or unsubstituted, saturated or unsaturated, aliphatic or aromatic, carbocyclic or heterocyclic 3-8 membered ring (e.g. cyclopropyl), C═O or ═N—OH;
- R₅is H, OH, SH, NH₂, NHNH₂, NHR, N(R₁₀)(R₁₁) (e.g., N(H)CH₃, N(H)CH₂CH₃), R₈—N(R₁₀)(R₁₁) (e.g. CH₂—NH₂); or R₂and R₅are joined to form a substituted or unsubstituted 4-8 membered heterocyclic ring (e.g. pyrrolidine);
- R₆and R₆₀are each independently H, F, Cl, Br, I, OH, SH, R₈—OH (e.g., CH₂—OH), R₈—SH, —R₈—O—R₁₀, (e.g., —CH₂—O—CH₃), R₈—(C₃-C₈cycloalkyl), R₈-(3-8 membered heterocyclic ring), CF₃, CD₃, OCD₃, CN, NO₂, —CH₂CN, —R₈CN, NH₂, NHR, N(R)₂, R₈—N(R₁₀)(R₁₁), R₉—R₈—N(R₁₀)(R₁₁), B(OH)₂, —OC(O)CF₃, —OCH₂Ph, NHC(O)—R₁₀(e.g., NHC(O)CH₃), NHC(O)—N(R₁₀)(R₁₁) (e.g., NHC(O)N(CH₃)₂), COOH, —C(O)Ph, C(O)O—R₁₀(e.g. C(O)O—CH₃), R₈—C(O)—R₁₀(e.g., CH₂C(O)CH₃), C(O)H, C(O)—R₁₀(e.g., C(O)—CH₃, C(O)—CH₂CH₃, C(O)—CH₂CH₂CH₃), C₁-C₈linear or branched C(O)-haloalkyl (e.g., C(O)—CF₃), —C(O)NH₂, C(O)NHR, C(O)N(R₁₀)(R₁₁) (e.g., C(O)N(CH₃)₂), SO₂R, SO₂N(R₁₀)(R₁₁) (e.g., SO₂N(CH₃)₂, SO₂NHC(O)CH₃), C₁-C₈linear or branched, substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl, benzyl), substituted or unsubstituted C₃-C₈cycloalkyl (e.g., cyclopropyl, cyclopentyl), C₂-C₈linear or branched, substituted or unsubstituted alkenyl (e.g., ethenyl), C₂-C₈linear or branched, substituted or unsubstituted alkynyl (e.g., ethynyl, CC—CH₂-cyclobutyl, CC—CF₃), C₁-C₈linear or branched or C₃-C₈cyclic haloalkyl (e.g., CF₃, CF₂CH₃, CH₂CF₃, CF₂CH₂CH₃, CH₂CH₂CF₃, CF₂CH(CH₃)₂, CF(CH₃)—CH(CH₃)₂), substituted or unsubstituted C₁-C₅linear or branched or C₃-C₈cyclic alkoxy (e.g. methoxy, ethoxy, propoxy, isopropoxy, O—CH₂—CF₃), optionally wherein at least one methylene group (CH₂) in the alkoxy is replaced with an oxygen atom, C₁-C₈linear or branched thioalkoxy, C₁-C₈linear or branched haloalkoxy (e.g., OCF₃, OCHF₂), substituted or unsubstituted 3-8 membered heterocyclic ring (e.g., thiophene, oxazole, oxadiazole, imidazole, furane, triazole, tetrazole, pyridine, pyrimidine, pyrazine), substituted or unsubstituted aryl (e.g., phenyl), substituted or unsubstituted benzyl;
- X₁is O, S, NH, NR (e.g., N—CH₃), S═O, SO₂; or X₁and R₄are joined to form a 4-8 membered heterocyclic ring (e.g., pyrrolidine);
- X₆is O, NH, NR or CH₂;
- G=X is C═O or SO₂or G(═X)—X₆—R₁is a tetrazole moiety;
- R₈is [CH₂]p
  - wherein p is between 1 and 10;
- R₉is [CH]_q, [C]_q
  - wherein q is between 2 and 10;
- R₁₀and R₁₁are each independently H, CN, C₁-C₈linear or branched alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH₃)), or S(O)₂R;
- or R₁₀and R₁₁are joined to form a substituted or unsubstituted 3-8 membered heterocyclic ring;
- R is H, C₁-C₈linear or branched alkyl (e.g., methyl, ethyl), C₁-C₈linear or branched alkoxy (e.g., methoxy), phenyl, aryl or heteroaryl, or two gem R substituents are joined together to form a 5 or 6 membered heterocyclic ring;
- k is an integer number between 1 and 3 (e.g., 1, 2);
  
  or agrochemically acceptable salt, zwitterion (inner salt), stereoisomer, tautomer, hydrate, N-oxide, reverse amide analog, isotopic variant (e.g., deuterated analog), or any combination thereof.

In various embodiments, if k is not 1, then R₂is H. In various embodiments, if k is 2, then R₂is H. In various embodiments, if k is 3, then R₂is H.

In various embodiments, ring C is cyclohexane, cyclohexene, isoxazole, triazole, pyrazole, oxadiazole, furan, thiazole, pyrrole or thiophene; each represents a separate embodiment according to this invention.

In various embodiments, ring C is represented by the following structure:

embedded image

wherein

- X₂, X₃, X₄and X₅are each independently N or C;

In various embodiments, at least one of X₂-X₅is N. In various embodiments, at least two of X₂-X₅are N. In various embodiments, X₂is N and X₃, X₄and X₅are C. In various embodiments, X₂and X₅are N and X₃and X₄are C. In various embodiments, X₃and X₅are N and X₂and X₄are C.

In various embodiments, this invention is directed to a compound represented by the structure of formula I(c):

embedded image

- wherein
  - each X₂, X₃, X₄and X₅is independently N or C; and
  - C1 represents a chiral carbon center;
- or its agrochemically acceptable salt, zwitterion (inner salt), hydrate, N-oxide, isotopic variant or any combination thereof.

In various embodiments, the compound of formula I(c) is chiral. In various embodiments, the compound of formula I(c) is a substantially pure single enantiomer. In various embodiments, the compound of formula I(c) is the R enantiomer. In various embodiments, compound of formula I(c) is the S enantiomer. In various embodiments, the compound comprises a single enantiomer in a purity of >80%. In various embodiments, the compound comprises a single enantiomer in a purity of >85%. In various embodiments, the compound comprises a single enantiomer in a purity of >90%. In various embodiments, the compound comprises a single enantiomer in a purity of >95%. In various embodiments, the compound comprises a single enantiomer in a purity of >99%.

In various embodiments, C1 of compound of formula I(c) has an R configuration. In various embodiments, C1 has an S configuration.

In various embodiments, at least one of X₂-X₅of compound of formula I(c) is N. In various embodiments, at least two of X₂-X₅are N. In various embodiments, X₂is N and X₃, X₄and X₅are C. In various embodiments, X₂and X₅are N and X₃and X₄are C. In various embodiments, X₃and X₅are N and X₂and X₄are C.

In various embodiments, this invention is directed to a compound represented by the structure of formula I(d):

embedded image

wherein

- B ring is absent, or is a substituted or unsubstituted aromatic or heteroaromatic ring system (e.g., aryl, pyridine), or a substituted or unsubstituted C₃-C₁₀cycloalkyl (cyclopropyl, cyclopentyl, cyclohexyl), or a substituted or unsubstituted C₃-C₁₀heterocyclic ring (e.g., pyrrolidine);
- R₁is H, substituted or unsubstituted C₁-C₁₀linear or branched, or C₃-C₈cyclic alkyl (e.g., methyl, ethyl, propyl, butyl, CH₂—CCH, CH₂—COOH, CH₂CH₂COOH), C(O)—R₁₀(e.g., C(O)—CH₃), R₈—OH (e.g., CH₂—OH), R₈—COO—R₁₀(e.g., CH₂—COOH, CH₂—COO—CH₃, CH₂—COO—CH₂CH₃, CH₂—CH₂—COOH, CH₂—CH₂—COO—CH₃, CH₂—CH₂—COO—CH₂CH₃), R₈—SH, —R₈—O—R₁₀, (e.g., —CH₂—O—CH₃), R₈—(C₃-C₈cycloalkyl), R₈-(3-8 membered heterocyclic ring), CF₃, NH₂, NHR, N(R)₂, R₈—N(R₁₀)(R₁₁), C(O)H, C₁-C₈linear or branched C(O)-haloalkyl (e.g., C(O)—CF₃), —C(O)NH₂, C(O)NHR, C(O)N(R₁₀)(Ru), C₂-C₈linear or branched, substituted or unsubstituted alkenyl (e.g., CH═C(Ph)₂), C₁-C₈linear or branched or C₃-C₈cyclic haloalkyl, substituted or unsubstituted 3-8 membered heterocyclic ring, substituted or unsubstituted aryl (e.g., phenyl), or substituted or unsubstituted benzyl;
- R₂is H, substituted or unsubstituted C₁-C₁₀linear or branched, or C₃-C₈cyclic alkyl (e.g., methyl, ethyl, propyl, CH₂—CCH), F, Cl, Br, I, OH, SH, R₈—OH (e.g., CH₂—OH), R₈—SH, —R₈—O—R₁₀, (e.g., —CH₂—O—CH₃), R₈—(C₃-C₈cycloalkyl), R₈-(3-8 membered heterocyclic ring), CF₃, CN, NO₂, R₈—N(R₁₀)(R₁₁), C(O)H, C₁-C₈linear or branched C(O)-haloalkyl (e.g., C(O)—CF₃), —C(O)NH₂, C(O)NHR, C(O)N(R₁₀)(R₁₁), C₂-C₈linear or branched, substituted or unsubstituted alkenyl (e.g., CH═C(Ph)₂), C₁-C₈linear or branched or C₃-C₈cyclic haloalkyl, substituted or unsubstituted 3-8 membered heterocyclic ring, substituted or unsubstituted aryl (e.g., phenyl), or substituted or unsubstituted benzyl;
- R₃is H, substituted or unsubstituted C₁-C₁₀linear or branched, or C₃-C₈cyclic alkyl (e.g., methyl, ethyl, propyl, CH₂—CCH, C(H)(OH)(CH₃)), F, Cl, Br, I, OH, SH, R₈—OH (e.g., CH₂—OH), R₈—SH, —R₈—O—R₁₀, (e.g., —CH₂—O—CH₃), R₈—(C₃-C₈cycloalkyl), R₈-(3-8 membered heterocyclic ring), CF₃, CN, NO₂, NH₂, NHR, N(R)₂, R₈—N(R₁₀)(R₁₁) (e.g. CH₂—NH₂); C(O)H, C₁-C₈linear or branched C(O)-haloalkyl (e.g., C(O)—CF₃), —C(O)NH₂, C(O)NHR, C(O)N(R₁₀)(R₁₁), C₂-C₈linear or branched, substituted or unsubstituted alkenyl (e.g., CH═C(Ph)₂), C₁-C₈linear or branched or C₃-C₈cyclic haloalkyl, substituted or unsubstituted 3-8 membered heterocyclic ring, substituted or unsubstituted aryl (e.g., phenyl), or substituted or unsubstituted benzyl;
- or R₂and R₃are joined to form a C₃-C₈substituted or unsubstituted, saturated or unsaturated, aliphatic (e.g. cyclopropyl, cyclopentyl, cyclohexyl), or aromatic (e.g. pyridine), carbocyclic or heterocyclic ring (e.g. pyrrolidine);
- R₄is H, substituted or unsubstituted C₁-C₁₀linear or branched, or C₃-C₈cyclic alkyl (e.g., methyl, ethyl, propyl, CH₂—CCH), F, Cl, Br, I, OH, SH, R₈—OH (e.g., CH₂—OH), R₈—SH, —R₈—O—R₁₀, (e.g., —CH₂—O—CH₃), R₈—(C₃-C₈cycloalkyl), R₈-(3-8 membered heterocyclic ring), CF₃, CN, NO₂, NH₂, NHR, N(R)₂, R₈—N(R₁₀)(R₁₁) (e.g. CH₂—NH₂), C(O)H, C₁-C₈linear or branched C(O)-haloalkyl (e.g., C(O)—CF₃), —C(O)NH₂, C(O)NHR, C(O)N(R₁₀)(R₁₁), C₂-C₈linear or branched, substituted or unsubstituted alkenyl (e.g., CH═C(Ph)₂), C₁-C₈linear or branched or C₃-C₈cyclic haloalkyl, substituted or unsubstituted 3-8 membered heterocyclic ring, substituted or unsubstituted aryl (e.g., phenyl), or substituted or unsubstituted benzyl;
- or R₃and R₄are joined to form a substituted or unsubstituted, saturated or unsaturated, aliphatic or aromatic, carbocyclic or heterocyclic 3-8 membered ring (e.g. cyclopropyl), C═O or ═N—OH;
- R₆and R₆₀are each independently H, F, Cl, Br, I, OH, SH, R₈—OH (e.g., CH₂—OH), R₈—SH, —R₈—O—R₁₀, (e.g., —CH₂—O—CH₃), R₈—(C₃-C₈cycloalkyl), R₈-(3-8 membered heterocyclic ring), CF₃, CD₃, OCD₃, CN, NO₂, —CH₂CN, —R₈CN, NH₂, NHR, N(R)₂, R₈—N(R₁₀)(R₁₁), R₉—R₈—N(R₁₀)(R₁₁), B(OH)₂, —OC(O)CF₃, —OCH₂Ph, NHC(O)—R₁₀(e.g., NHC(O)CH₃), NHC(O)—N(R₁₀)(R₁₁) (e.g., NHC(O)N(CH₃)₂), COOH, —C(O)Ph, C(O)O—R₁₀(e.g. C(O)O—CH₃), R₈—C(O)—R₁₀(e.g., CH₂C(O)CH₃), C(O)H, C(O)—R₁₀(e.g., C(O)—CH₃, C(O)—CH₂CH₃, C(O)—CH₂CH₂CH₃), C₁-C₈linear or branched C(O)-haloalkyl (e.g., C(O)—CF₃), —C(O)NH₂, C(O)NHR, C(O)N(R₁₀)(R₁₁) (e.g., C(O)N(CH₃)₂), SO₂R, SO₂N(R₁₀)(R₁₁) (e.g., SO₂N(CH₃)₂, SO₂NHC(O)CH₃), C₁-C₈linear or branched, substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl, benzyl), substituted or unsubstituted C₃-C₈cycloalkyl (e.g., cyclopropyl, cyclopentyl), C₂-C₈linear or branched, substituted or unsubstituted alkenyl (e.g., ethenyl), C₂-C₈linear or branched, substituted or unsubstituted alkynyl (e.g., ethynyl, CC—CH₂-cyclobutyl, CC—CF₃), C₁-C₈linear or branched or C₃-C₈cyclic haloalkyl (e.g., CF₃, CF₂CH₃, CH₂CF₃, CF₂CH₂CH₃, CH₂CH₂CF₃, CF₂CH(CH₃)₂, CF(CH₃)—CH(CH₃)₂), substituted or unsubstituted C₁-C₈linear or branched or C₃-C₈cyclic alkoxy (e.g. methoxy, ethoxy, propoxy, isopropoxy, O—CH₂—CF₃), optionally wherein at least one methylene group (CH₂) in the alkoxy is replaced with an oxygen atom, C₁-C₈linear or branched thioalkoxy, C₁-C₈linear or branched haloalkoxy (e.g., OCF₃, OCHF₂), substituted or unsubstituted 3-8 membered heterocyclic ring (e.g., thiophene, oxazole, oxadiazole, imidazole, furane, triazole, tetrazole, pyridine, pyrimidine, pyrazine), substituted or unsubstituted aryl (e.g., phenyl), substituted or unsubstituted benzyl;
- X₃, X₄, X₅are each independently C or N;
- X₆is O, NH, NR or CH₂;
- G=X is C═O or SO₂or G(═X)—X₆—R₁is a tetrazole moiety;
- R₈is [CH₂]p
  - wherein p is between 1 and 10;
- R₉is [CH]_q, [C]_q
  - wherein q is between 2 and 10;
- R₁₀and R₁₁are each independently H, CN, C₁-C₈linear or branched alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH₃)), or S(O)₂R;
- or R₁₀and R₁₁are joined to form a substituted or unsubstituted 3-8 membered heterocyclic ring;
- R is H, C₁-C₅linear or branched alkyl (e.g., methyl, ethyl), C₁-C₅linear or branched alkoxy (e.g., methoxy), phenyl, aryl or heteroaryl, or two gem R substituents are joined together to form a 5 or 6 membered heterocyclic ring;
- k is an integer number between 1 and 3 (e.g., 1, 2);
  
  or agrochemically acceptable salt, zwitterion (inner salt), stereoisomer, tautomer, hydrate, N-oxide, reverse amide analog, isotopic variant (e.g., deuterated analog), or any combination thereof.

In various embodiments, if k is not 1, then R₂is H. In various embodiments, if k is 2, then R₂is H. In various embodiments, if k is 3, then R₂is H.

In various embodiments, this invention is directed to a compound represented by the structure of formula I(e):

embedded image

wherein

- B ring is absent, or is a substituted or unsubstituted aromatic or heteroaromatic ring system (e.g., aryl, pyridine), or a substituted or unsubstituted C₃-C₁₀cycloalkyl (cyclopropyl, cyclopentyl, cyclohexyl), or a substituted or unsubstituted C₃-C₁₀heterocyclic ring (e.g., pyrrolidine); C ring is a saturated or unsaturated, 5 membered heterocyclic ring (e.g., isoxazole, triazole, pyrazole, oxadiazole, furan, thiazole, pyrrole, thiophene), a cyclohexane or a cyclohexene ring;
- R₁is H, substituted or unsubstituted C₁-C₁₀linear or branched, or C₃-C₈cyclic alkyl (e.g., methyl, ethyl, propyl, butyl, CH₂—CCH, CH₂—COOH, CH₂CH₂COOH), C(O)—R₁₀(e.g., C(O)—CH₃), R₈—OH (e.g., CH₂—OH), R₈—COO—R₁₀(e.g., CH₂—COOH, CH₂—COO—CH₃, CH₂—COO—CH₂CH₃, CH₂—CH₂—COOH, CH₂—CH₂—COO—CH₃, CH₂—CH₂—COO—CH₂CH₃), R₈—SH, —R₈—O—R₁₀, (e.g., —CH₂—O—CH₃), R₈—(C₃-C₈cycloalkyl), R₈-(3-8 membered heterocyclic ring), CF₃, NH₂, NHR, N(R)₂, R₈—N(R₁₀)(R₁₁), C(O)H, C₁-C₅linear or branched C(O)-haloalkyl (e.g., C(O)—CF₃), —C(O)NH₂, C(O)NHR, C(O)N(R₁₀)(R₁₁), C₂-C₅linear or branched, substituted or unsubstituted alkenyl (e.g., CH═C(Ph)₂), C₁-C₅linear or branched or C₃-C₈cyclic haloalkyl, substituted or unsubstituted 3-8 membered heterocyclic ring, substituted or unsubstituted aryl (e.g., phenyl), or substituted or unsubstituted benzyl
- R₂is H, substituted or unsubstituted C₁-C₁₀linear or branched, or C₃-C₈cyclic alkyl (e.g., methyl, ethyl, propyl, CH₂—CCH), F, Cl, Br, I, OH, SH, R₈—OH (e.g., CH₂—OH), R₈—SH, —R₈—O—R₁₀, (e.g., —CH₂—O—CH₃), R₈—(C₃-C₈cycloalkyl), R₈-(3-8 membered heterocyclic ring), CF₃, CN, NO₂, R₈—N(R₁₀)(R₁₁), C(O)H, C₁-C₅linear or branched C(O)-haloalkyl (e.g., C(O)—CF₃), —C(O)NH₂, C(O)NHR, C(O)N(R₁₀)(R₁₁), C₂-C₅linear or branched, substituted or unsubstituted alkenyl (e.g., CH═C(Ph)₂), C₁-C₅linear or branched or C₃-C₈cyclic haloalkyl, substituted or unsubstituted 3-8 membered heterocyclic ring, substituted or unsubstituted aryl (e.g., phenyl), or substituted or unsubstituted benzyl;
- R₃is H, substituted or unsubstituted C₁-C₁₀linear or branched, or C₃-C₈cyclic alkyl (e.g., methyl, ethyl, propyl, CH₂—CCH, C(H)(OH)(CH₃)), F, Cl, Br, I, OH, SH, R₈—OH (e.g., CH₂—OH), R₈—SH, —R₈—O—R₁₀, (e.g., —CH₂—O—CH₃), R₈—(C₃-C₈cycloalkyl), R₈-(3-8 membered heterocyclic ring), CF₃, CN, NO₂, NH₂, NHR, N(R)₂, R₈—N(R₁₀)(R₁₁) (e.g. CH₂—NH₂); C(O)H, C₁-C₅linear or branched C(O)-haloalkyl (e.g., C(O)—CF₃), —C(O)NH₂, C(O)NHR, C(O)N(R₁₀)(R₁₁), C₂-C₅linear or branched, substituted or unsubstituted alkenyl (e.g., CH═C(Ph)₂), C₁-C₅linear or branched or C₃-C₈cyclic haloalkyl, substituted or unsubstituted 3-8 membered heterocyclic ring, substituted or unsubstituted aryl (e.g., phenyl), or substituted or unsubstituted benzyl;
- or R₂and R₃are joined to form ring B as described above;
- R₄is H, substituted or unsubstituted C₁-C₁₀linear or branched, or C₃-C₈cyclic alkyl (e.g., methyl, ethyl, propyl, CH₂—CCH), F, Cl, Br, I, OH, SH, R₈—OH (e.g., CH₂—OH), R₈—SH, —R₈—O—R₁₀, (e.g., —CH₂—O—CH₃), R₈—(C₃-C₈cycloalkyl), R₈-(3-8 membered heterocyclic ring), CF₃, CN, NO₂, NH₂, NHR, N(R)₂, R₈—N(R₁₀)(R₁₁) (e.g. CH₂—NH₂), C(O)H, C₁-C₈linear or branched C(O)-haloalkyl (e.g., C(O)—CF₃), —C(O)NH₂, C(O)NHR, C(O)N(R₁₀)(R₁₁), C₂-C₈linear or branched, substituted or unsubstituted alkenyl (e.g., CH═C(Ph)₂), C₁-C₈linear or branched or C₃-C₈cyclic haloalkyl, substituted or unsubstituted 3-8 membered heterocyclic ring, substituted or unsubstituted aryl (e.g., phenyl), or substituted or unsubstituted benzyl or R₃and R₄are joined to form a substituted or unsubstituted, saturated or unsaturated, aliphatic or aromatic, carbocyclic or heterocyclic 3-8 membered ring (e.g. cyclopropyl), C═O or ═N—OH;
- R₆and R₆₀are each independently H, F, Cl, Br, I, OH, SH, R₈—OH (e.g., CH₂—OH), R₈—SH, —R₈—O—R₁₀, (e.g., —CH₂—O—CH₃), R₈—(C₃-C₈cycloalkyl), R₈-(3-8 membered heterocyclic ring), CF₃, CD₃, OCD₃, CN, NO₂, —CH₂CN, —R₈CN, NH₂, NHR, N(R)₂, R₈—N(R₁₀)(R₁₁), R₉—R₈—N(R₁₀)(R₁₁), B(OH)₂, —OC(O)CF₃, —OCH₂Ph, NHC(O)—R₁₀(e.g., NHC(O)CH₃), NHC(O)—N(R₁₀)(R₁₁) (e.g., NHC(O)N(CH₃)₂), COOH, —C(O)Ph, C(O)O—R₁₀(e.g. C(O)O—CH₃), R₈—C(O)—R₁₀(e.g., CH₂C(O)CH₃), C(O)H, C(O)—R₁₀(e.g., C(O)—CH₃, C(O)—CH₂CH₃, C(O)—CH₂CH₂CH₃), C₁-C₈linear or branched C(O)-haloalkyl (e.g., C(O)—CF₃), —C(O)NH₂, C(O)NHR, C(O)N(R₁₀)(Ru) (e.g., C(O)N(CH₃)₂), SO₂R, SO₂N(R₁₀)(R₁₁) (e.g., SO₂N(CH₃)₂, SO₂NHC(O)CH₃), C₁-C₅linear or branched, substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl, benzyl), substituted or unsubstituted C₃-C₈cycloalkyl (e.g., cyclopropyl, cyclopentyl), C₂-C₅linear or branched, substituted or unsubstituted alkenyl (e.g., ethenyl), C₂-C₅linear or branched, substituted or unsubstituted alkynyl (e.g., ethynyl, CC—CH₂-cyclobutyl, CC—CF₃), C₁-C₈linear or branched or C₃-C₈cyclic haloalkyl (e.g., CF₃, CF₂CH₃, CH₂CF₃, CF₂CH₂CH₃, CH₂CH₂CF₃, CF₂CH(CH₃)₂, CF(CH₃)—CH(CH₃)₂), substituted or unsubstituted C₁-C₅linear or branched or C₃-C₈cyclic alkoxy (e.g. methoxy, ethoxy, propoxy, isopropoxy, O—CH₂—CF₃), optionally wherein at least one methylene group (CH₂) in the alkoxy is replaced with an oxygen atom, C₁-C₅linear or branched thioalkoxy, C₁-C₅linear or branched haloalkoxy (e.g., OCF₃, OCHF₂), substituted or unsubstituted 3-8 membered heterocyclic ring (e.g., thiophene, oxazole, oxadiazole, imidazole, furane, triazole, tetrazole, pyridine, pyrimidine, pyrazine), substituted or unsubstituted aryl (e.g., phenyl), substituted or unsubstituted benzyl,
- X₆is O, NH, NR or CH₂;
- G=X is C═O or SO₂or G(═X)—X₆—R₁is a tetrazole moiety;
- R₈is [CH₂]p
  - wherein p is between 1 and 10;
- R₉is [CH]_q, [C]_q
  - wherein q is between 2 and 10;
- R₁₀and R₁₁are each independently H, CN, C₁-C₅linear or branched alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH₃)), or S(O)₂R;
- or R₁₀and R₁₁are joined to form a substituted or unsubstituted 3-8 membered heterocyclic ring;
- R is H, C₁-C₅linear or branched alkyl (e.g., methyl, ethyl), C₁-C₅linear or branched alkoxy (e.g., methoxy), phenyl, aryl or heteroaryl, or two gem R substituents are joined together to form a 5 or 6 membered heterocyclic ring; and
- k is an integer number between 1 and 3;
  
  or its agrochemically acceptable salt, zwitterion (inner salt), stereoisomer, tautomer, hydrate, N-oxide, reverse amide analog, isotopic variant (e.g., deuterated analog), or any combination thereof.

In various embodiments, if k is not 1, then R₂is H. In various embodiments, if k is 2, then R₂is H. In various embodiments, if k is 3, then R₂is H.

In various embodiments, compound of formula I, or I(a)-I(e) is not: 6-(2-aminopropoxy)picolinic acid. In various embodiments, the compound is not 6-(2-aminopropoxy)pyrazine-2-carboxylic acid. In various embodiments, the compound is not 2-(2-aminopropoxy)pyrimidine-4-carboxylic acid In various embodiments, the compound is not 6-(2-aminopropoxy)-3-fluoropicolinic acid. In various embodiments, the compound is not 6-(2-aminopropoxy)-4-fluoropicolinic acid. In various embodiments, the compound is not 6-(2-aminobutoxy)picolinic acid. In various embodiments, the compound is not 6-((2-aminocyclopentyl)oxy)picolinic acid. In various embodiments, the compound is not methyl 6-(2-aminopropoxy)picolinate. In various embodiments, the compound is not ethyl 6-(2-aminopropoxy)picolinate.

It is understood that the compounds according to this invention may be also present in their inner salt form (i.e., zwitterion). Accordingly, in solution a chemical equilibrium will be established between the “parent” molecule and its zwitterionic form.

In various embodiments, the compound is an herbicide. In various embodiments, the compound is an herbicidal compound. In various embodiments, the compound is a pesticide. In various embodiments, the compound is a pesticidal compound.

In various embodiments, this invention is directed to a compound represented by any one of the following structures:

TABLE 1

Compound

Number
Structure

101

embedded image

102

103

104

105

106

107

108

109

110

111

112

113

114

115

116

117

118

119

120

121

122

123

124

125

126

127

128

129

130

131

132

133

134

135

136

137

138

139

140

141

142

143

144

145

146

147

148

149

150

151

152

153

154

155

156

157

158

159

160

161

162

163

164

165

166

167

168

169

170

171

172

173

174

175

176

177

178

179

180

181

182

183

184

185

186

187

188

189

190

191

192

193

194

195

196

197

198

199

200

201

202

203

204

205

206

207

208

209

210

211

212

213

214

215

216

218

219

400

401

402

403

404

405

406

407

408

409

410

411

412

413

414

415

In various embodiments, the compound is an herbicide. In various embodiments, the compound is a pesticide. In various embodiments, the compound is herbicidal compound. In various embodiments, the compound is pesticidal compound.

In various embodiments, this invention is directed to a compound represented by any one of the following structures:

TABLE 2

Compound

Number
Structure

157

embedded image

161

169

170

171

174

175

176

177

179

180

181

182

183

184

185

188

190

191

192

193

194

195

196

197

198

199

200

201

202

203

204

205

206

207

208

209

210

211

212

213

215

216

In various embodiments, this invention is directed to a use of a compound represented by any one of the structures of Tables 1 or 2, or an agrochemical composition thereof, in controlling the growth of undesired plants; each structure represents a separate embodiment according to this invention.

In some embodiments, A of formula I, I(a), I(b), and/or I(c) is absent. In some embodiments, A is a substituted or unsubstituted single or fused aromatic or heteroaromatic ring system, or a substituted or unsubstituted single or fused C₃-C₁₀cycloalkyl, or a substituted or unsubstituted single or fused C₃-C₁₀heterocyclic ring; each is a separate embodiment according to this invention. In some embodiments, A is a single aromatic ring system. In some embodiments, A is a single heteroaromatic ring. In some embodiments, A is a single C₃-C₁₀cycloalkyl. In some embodiments, A is cyclopropyl. In some embodiments, A is a single C₃-C₁₀heterocyclic ring. In some embodiments, A is a fused aromatic ring system. In some embodiments, A is a fused heteroaromatic ring system. In some embodiments, A is a fused C₃-C₁₀cycloalkyl. In some embodiments, A is a fused C₃-C₁₀heterocyclic ring system. In other embodiments, A is cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl; each represents a separate embodiment according to this invention. In some embodiments, A ring may be further substituted, with at least one substituent selected from: C(O)—CH₃, C₁-C₅linear or branched, substituted or unsubstituted alkyl, methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl, benzyl, F, Cl, Br, I, OH, SH, C₁-C₅linear or branched alkyl, C₃-C₈cycloalkyl (e.g., cyclopentyl), C₂-C₅linear or branched alkenyl (e.g., ethenyl), C₂-C₅linear or branched alkynyl, alkyl amide (i.e., C(O)NH—R or NHC(O)—R), linear, branched or cyclic alkoxy, COOH, alkyl ester (i.e., COOR or OC(O)—R), OH, COO(R), N(R)₂, NH₂, CF₃, aryl, phenyl, heteroaryl, R₈—(C₃-C₈cycloalkyl), halophenyl, CN, NO₂or any combination thereof; each represents a separate embodiment according to this invention.

In some embodiments, B of formula I, I(a), I(b), I(c), I(d) and/or I(e) is absent. In some embodiments, ring B is a substituted or unsubstituted single or fused aromatic or heteroaromatic ring system, or a substituted or unsubstituted single or fused C₃-C₁₀cycloalkyl, or a substituted or unsubstituted single or fused C₃-C₁₀heterocyclic ring; each represents a separate embodiment according to this invention. In some embodiments, B is a single aromatic ring system (i.e., arene). In some embodiments, B is a single heteroaromatic ring (e.g., pyridine). In some embodiments, B is a single C₃-C₁₀cycloalkyl (e.g., cyclopropyl, cyclopentyl, cyclohexyl). In some embodiments, B is a single C₃-C₁₀heterocyclic ring (e.g., pyrrolidinyl). In some embodiments, B is a fused aromatic ring system. In some embodiments, B is a fused heteroaromatic ring system. In some embodiments, B is a fused C₃-C₁₀cycloalkyl. In some embodiments, B is a fused C₃-C₁₀heterocyclic ring system. In some embodiments, B is a single C₃-C₁₀cycloalkyl. In some embodiments, B is cyclopentyl. In some embodiments, B is cyclohexyl. In some embodiments, B is cyclopropyl. In some embodiments, B may be further substituted, with at least one substituent selected from: F, Cl, Br, I, OH, SH, R₈—OH, R₈—SH, —R₈—O—R₁₀, CF₃, CN, NO₂, NH₂, NHR, N(R)₂, R₈—N(R₁₀)(R₁₁), —OC(O)CF₃, —OCH₂Ph, NHC(O)OBz, —NHC(O)—R₁₀, COOH, —C(O)Ph, C(O)O—R₁₀, C(O)H, C(O)—R₁₀, C₁-C₅linear or branched C(O)-haloalkyl, —C(O)NH₂, C(O)NHR, C(O)N(R₁₀)(R₁₁), SO₂R, SO₂N(R₁₀)(R₁₁), C₁-C₅linear or branched or C₃-C₈cyclic haloalkyl, C₁-C₅linear or branched or C₃-C₈cyclic alkoxy, C₁-C₅linear or branched thioalkoxy, C₁-C₅linear or branched haloalkoxy, C₁-C₅linear or branched alkoxyalkyl, substituted or unsubstituted C₃-C₈cycloalkyl, substituted or unsubstituted 3-8 membered heterocyclic ring, substituted or unsubstituted aryl, C(O)—CH₃, C₁-C₅linear or branched, substituted or unsubstituted alkyl, methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl, benzyl, C₂-C₅linear or branched alkenyl (e.g., ethenyl), C₂-C₅linear or branched alkynyl, alkyl ester (i.e., COOR or OC(O)—R), aryl, phenyl, R₈—(C₃-C₈cycloalkyl), and halophenyl; each represents a separate embodiment according to this invention.

In some embodiments, C ring of formula I(b) or I(e) is a saturated or unsaturated, 5 membered heterocyclic ring. In some embodiments, C is isoxazole. In some embodiments, C is triazole. In some embodiments, C is pyrazole. In some embodiments, C is oxadiazole. In some embodiments, C is furan. In some embodiments, C is thiazole. In some embodiments, C is pyrrole. In some embodiments, C is thiophene. In some embodiments, C is isoxazole, triazole, pyrazole, oxadiazole, furan, thiazole, pyrrole, thiophene; each represents a separate embodiment according to this invention. In some embodiments, C ring is cyclohexane. In some embodiments, C ring is cyclohexene. In some embodiments, C ring is represented by any one of the following structures:

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