Pesticidal and herbicidal compounds and methods of use thereof

A compound represented by the structure of formula I(d):

• wherein
• B ring is absent, or is a substituted or unsubstituted heteroaromatic ring system, or a substituted or unsubstituted C3-C10 cycloalkyl, or a substituted or unsubstituted C3-C10 heterocyclic ring (e.g., cyclopropyl, cyclopentyl, cyclohexyl, pyridyl, pyrrolidinyl);
• R1 is H, substituted or unsubstituted C1-C10 linear or branched, or C3-C8 cyclic alkyl (e.g., methyl, ethyl, propyl, butyl, CH2—CCH, CH2—C(O)OH, CH2CH2C(O)OH), C(O)—R10 (e.g., C(O)—CH3), R8—OH (e.g., CH2—OH), R8—C(O)O—R10 (e.g., CH2—C(O)OH, CH2—C(O)O—CH3, CH2—C(O)O—CH2CH3, CH2—CH2—C(O)OH, CH2—CH2—C(O)O—CH3, CH2—CH2—C(O)O—CH2CH3), R8—SH, —R8—O—R10, (e.g., —CH2—O—CH3), R8—(C3-C8 cycloalkyl), R8-(3-8 membered heterocyclic ring), CF3, NH2, NHR, N(R)2, R8—N(R10)(R11), C(O)H, C1-C5 linear or branched C(O)-haloalkyl (e.g., C(O)—CF3), —C(O)NH2, C(O)NHR, C(O)N(R10)(R11), C2-C5 linear or branched, substituted or unsubstituted alkenyl (e.g., CH═C(Ph)2), C1-C5 linear or branched or C3-C8 cyclic haloalkyl, substituted or unsubstituted C3-C8 heterocyclic ring, substituted or unsubstituted aryl (e.g., phenyl), or substituted or unsubstituted benzyl
• R2 is H, substituted or unsubstituted C1-C10 linear or branched, or C3-C8 cyclic 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-C8 cycloalkyl), R8-(3-8 membered heterocyclic ring), CF3, CN, NO2, R8—N(R10)(R11), C(O)H, C1-C5 linear or branched C(O)-haloalkyl (e.g., C(O)—CF3), —C(O)NH2, C(O)NHR, C(O)N(R10)(Rn), C2-C5 linear or branched, substituted or unsubstituted alkenyl (e.g., CH═C(Ph)2), C1-C5 linear or branched or C3-C8 cyclic haloalkyl, substituted or unsubstituted 3-8 membered heterocyclic ring, substituted or unsubstituted aryl (e.g., phenyl), or substituted or unsubstituted benzyl;
• R3 is H, substituted or unsubstituted C1-C10 linear or branched, or C3-C8 cyclic 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-C8 cycloalkyl), R8-(3-8 membered heterocyclic ring), CF3, CN, NO2, NH2, NHR, N(R)2, R8—N(R10)(Rn) (e.g. CH2—NH2);
• C(O)H, C1-C5 linear or branched C(O)-haloalkyl (e.g., C(O)—CF3), —C(O)NH2, C(O)NHR, C(O)N(R10)(R11), C2-C5 linear or branched, substituted or unsubstituted alkenyl (e.g., CH═C(Ph)2), C1-C5 linear or branched or C3-C8 cyclic haloalkyl, substituted or unsubstituted 3-8 membered heterocyclic ring, substituted or unsubstituted aryl (e.g., phenyl), or substituted or unsubstituted benzyl;
• or R2 and R3 are joined to form ring B as described above;
• R4 is H, substituted or unsubstituted C1-C10 linear or branched, or C3-C8 cyclic 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-C8 cycloalkyl), R8-(3-8 membered heterocyclic ring), CF3, CN, NO2, NH2, NHR, N(R)2, R8—N(R10)(Rn) (e.g. CH2—NH2), C(O)H, C1-C5 linear or branched C(O)-haloalkyl (e.g., C(O)—CF3), —C(O)NH2, C(O)NHR, C(O)N(R10)(R11), C2-C5 linear or branched, substituted or unsubstituted alkenyl (e.g., CH═C(Ph)2), C1-C5 linear or branched or C3-C8 cyclic haloalkyl, substituted or unsubstituted 3-8 membered heterocyclic ring, substituted or unsubstituted aryl (e.g., phenyl), or substituted or unsubstituted benzyl
• or R3 and R4 are joined to form a C3-C8 substituted or unsubstituted, saturated or unsaturated, aliphatic or aromatic, carbocyclic or heterocyclic ring (e.g. cyclopropyl), C═O or ═N—OH;
• R6 and R60 are 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-C8 cycloalkyl), R8-(3-8 membered heterocyclic ring), CF3, CD3, OCD3, CN, NO2, —CH2CN, —R8CN, NH2, NHR, N(R)2, R8—N(R10)(Rn), R9—R8—N(R10)(Rn), B(OH)2, —OC(O)CF3, —OCH2Ph, NHC(O)—R10 (e.g., NHC(O)CH3), NHC(O)—N(R10)(Rn) (e.g., NHC(O)N(CH3)2), C(O)OH, —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-C5 linear 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-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl, benzyl), substituted or unsubstituted C3-C8 cycloalkyl (e.g., cyclopropyl, cyclopentyl), C2-C5 linear or branched, substituted or unsubstituted alkenyl (e.g., ethenyl), C2-C5 linear or branched, substituted or unsubstituted alkynyl (e.g., ethynyl, CC—CH2-cyclobutyl, CC—CF3), C1-C5 linear or branched or C3-C8 cyclic haloalkyl (e.g., CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)—CH(CH3)2), substituted or unsubstituted C1-C5 linear or branched or C3-C8 cyclic 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-C5 linear or branched thioalkoxy, C1-C5 linear 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, X5 are each independently C or N;
• X6 is O or CH2;
• G=X is C═O or SO2 or G(═X)—X6—R1 is a tetrazole moiety;
• R8 is [CH2]q
• wherein p is between 1 and 10;
• R9 is [CH]q, [C]q
• wherein q is between 2 and 10;
• R10 and R11 are each independently H, CN, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH3)), or S(O)2R;
• or R10 and R11 are joined to form a substituted or unsubstituted 3-8 membered heterocyclic ring;
• R is H, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C1-C5 linear 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 a compound represented by the structure of formula I(e):
• wherein
• B ring is absent, or is a substituted or unsubstituted single or fused aromatic or heteroaromatic ring system, or a substituted or unsubstituted single or fused C3-C10 cycloalkyl, or a substituted or unsubstituted single or fused C3-C10 heterocyclic ring;
• 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;
• R1 is H, substituted or unsubstituted C1-C10 linear or branched, or C3-C8 cyclic alkyl (e.g., methyl, ethyl, propyl, butyl, CH2—CCH, CH2—C(O)OH, CH2CH2C(O)OH), C(O)—R10 (e.g., C(O)—CH3), R8—OH (e.g., CH2—OH), R8—C(O)O—R10 (e.g., CH2—C(O)OH, CH2—C(O)O—CH3, CH2—C(O)O—CH2CH3, CH2—CH2—C(O)OH, CH2—CH2—C(O)O—CH3, CH2—CH2—C(O)O—CH2CH3), R8—SH, —R8—O—R10, (e.g., —CH2—O—CH3), R8—(C3-C8 cycloalkyl), R8-(3-8 membered heterocyclic ring), CF3, NH2, NHR, N(R)2, R8—N(R10)(R11), C(O)H, C1-C5 linear or branched C(O)-haloalkyl (e.g., C(O)—CF3), —C(O)NH2, C(O)NHR, C(O)N(R10)(Rn), C2-C5 linear or branched, substituted or unsubstituted alkenyl (e.g., CH═C(Ph)2), C1-C5 linear or branched or C3-C8 cyclic haloalkyl, substituted or unsubstituted 3-8 membered heterocyclic ring, substituted or unsubstituted aryl (e.g., phenyl), or substituted or unsubstituted benzyl
• R2 is H, substituted or unsubstituted C1-C10 linear or branched, or C3-C8 cyclic 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-C8 cycloalkyl), R8-(3-8 membered heterocyclic ring), CF3, CN, NO2, R8—N(R10)(R11), C(O)H, C1-C5 linear or branched C(O)-haloalkyl (e.g., C(O)—CF3), —C(O)NH2, C(O)NHR, C(O)N(R10)(Rn), C2-C5 linear or branched, substituted or unsubstituted alkenyl (e.g., CH═C(Ph)2), C1-C5 linear or branched or C3-C8 cyclic haloalkyl, substituted or unsubstituted 3-8 membered heterocyclic ring, substituted or unsubstituted aryl (e.g., phenyl), or substituted or unsubstituted benzyl;
• R3 is H, substituted or unsubstituted C1-C10 linear or branched, or C3-C8 cyclic 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-C8 cycloalkyl), R8-(3-8 membered heterocyclic ring), CF3, CN, NO2, NH2, NHR, N(R)2, R8—N(R10)(Rn) (e.g. CH2—NH2);
• C(O)H, C1-C5 linear or branched C(O)-haloalkyl (e.g., C(O)—CF3), —C(O)NH2, C(O)NHR, C(O)N(R10)(R11), C2-C5 linear or branched, substituted or unsubstituted alkenyl (e.g., CH═C(Ph)2), C1-C5 linear or branched or C3-C8 cyclic haloalkyl, substituted or unsubstituted 3-8 membered heterocyclic ring, substituted or unsubstituted aryl (e.g., phenyl), or substituted or unsubstituted benzyl;
• or R2 and R3 are Joined to form ring B as described above;
• R4 is H, substituted or unsubstituted C1-C10 linear or branched, or C3-C8 cyclic 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-C8 cycloalkyl), 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-C5 linear or branched C(O)-haloalkyl (e.g., C(O)—CF3), —C(O)NH2, C(O)NHR, C(O)N(R10)(R11), C2-C5 linear or branched, substituted or unsubstituted alkenyl (e.g., CH═C(Ph)2), C1-C5 linear or branched or C3-C8 cyclic haloalkyl, substituted or unsubstituted 3-8 membered heterocyclic ring, substituted or unsubstituted aryl (e.g., phenyl), or substituted or unsubstituted benzyl
• or R3 and R4 are joined to form a C3-C8 substituted or unsubstituted, saturated or unsaturated, aliphatic or aromatic, carbocyclic or heterocyclic ring (e.g. cyclopropyl), C═O or ═N—OH;
• R6 and R60 are 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-C8 cycloalkyl), 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-C5 linear 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-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl, benzyl), substituted or unsubstituted C3-C8 cycloalkyl (e.g., cyclopropyl, cyclopentyl), C2-C5 linear or branched, substituted or unsubstituted alkenyl (e.g., ethenyl), C2-C5 linear or branched, substituted or unsubstituted alkynyl (e.g., ethynyl, CC—CH2-cyclobutyl, CC—CF3), C1-C5 linear or branched or C3-C8 cyclic haloalkyl (e.g., CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)—CH(CH3)2), substituted or unsubstituted C1-C5 linear or branched or C3-C8 cyclic 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-C5 linear or branched thioalkoxy, C1-C5 linear 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,
• X6 is O, NH, NR or CH2;
• G=X is C═O or SO2 or G(═X)—X6—R1 is a tetrazole moiety;
• R8 is [CH2]q
• wherein p is between 1 and 10;
• R9 is [CH]q, [C]q
• wherein q is between 2 and 10;
• R10 and R11 are each independently H, CN, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH3)), or S(O)2R;
• or R10 and R11 are joined to form a substituted or unsubstituted 3-8 membered heterocyclic ring;
• R is H, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C1-C5 linear 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 a compound represented by any one of the following structures:
• Compound
• Number
• Structure
• 161
• 178
• 186
• 187
• 189
• 214
• or its agrochemically acceptable salt, zwitterion (inner salt), hydrate, N-oxide, isotopic variant or any combination thereof,
• wherein the compound is not:
• 6-(2-aminopropoxy)picolinic;
• 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.

A method for controlling the growth of undesired plants, comprising applying a compound or an agrochemical composition thereof, to a crop field, wherein the compound is represented by the structure of formula I:

• wherein
• A ring is absent, or is a substituted or unsubstituted single or fused aromatic or heteroaromatic ring system, or a substituted or unsubstituted single or fused C3-C10 cycloalkyl, or a substituted or unsubstituted single or fused C3-C10 heterocyclic ring (e.g., cyclopropyl);
• B ring is absent, or is a substituted or unsubstituted single or fused heteroaromatic ring system, or a substituted or unsubstituted single or fused C3-C10 cycloalkyl, or a substituted or unsubstituted single or fused C3-C10 heterocyclic ring (e.g., cyclopentyl);
• R1 is H, substituted or unsubstituted C1-C10 linear or branched, or C3-C8 cyclic alkyl (e.g., methyl, ethyl, propyl, butyl, CH2—CCH, CH2—C(O)OH, CH2CH2C(O)OH), C(O)—R10 (e.g., C(O)—CH3), R8—OH (e.g., CH2—OH), R8—C(O)O—R10 (e.g., CH2—C(O)OH, CH2—C(O)O—CH3, CH2—C(O)O—CH2CH3, CH2—CH2—C(O)OH, CH2—CH2—C(O)O—CH3, CH2—CH2—C(O)O—CH2CH3), R8—SH, —R8—O—R10, (e.g., —CH2—O—CH3), R8—(C3-C8 cycloalkyl), R8-(3-8 membered heterocyclic ring), CF3, NH2, NHR, N(R)2, R8—N(R10)(R11), C(O)H, C1-C5 linear or branched C(O)-haloalkyl (e.g., C(O)—CF3), —C(O)NH2, C(O)NHR, C(O)N(R10)(Rn), C2-C5 linear or branched, substituted or unsubstituted alkenyl (e.g., CH═C(Ph)2), C1-C5 linear or branched or C3-C8 cyclic haloalkyl, substituted or unsubstituted 3-8 membered heterocyclic ring, substituted or unsubstituted aryl (e.g., phenyl), or substituted or unsubstituted benzyl
• R2 is H, substituted or unsubstituted C1-C10 linear or branched, or C3-C8 cyclic 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-C8 cycloalkyl), R8-(3-8 membered heterocyclic ring), CF3, CN, NO2, R8—N(R10)(R11), C(O)H, C1-C5 linear or branched C(O)-haloalkyl (e.g., C(O)—CF3), —C(O)NH2, C(O)NHR, C(O)N(R10)(Rn), C2-C5 linear or branched, substituted or unsubstituted alkenyl (e.g., CH═C(Ph)2), C1-C5 linear or branched or C3-C8 cyclic haloalkyl, substituted or unsubstituted 3-8 membered heterocyclic ring, substituted or unsubstituted aryl (e.g., phenyl), or substituted or unsubstituted benzyl;
• R3 is H, substituted or unsubstituted C1-C10 linear or branched, or C3-C8 cyclic 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-C8 cycloalkyl), R8-(3-8 membered heterocyclic ring), CF3, CN, NO2, NH2, NHR, N(R)2, R8—N(R10)(Rn) (e.g. CH2—NH2);
• C(O)H, C1-C5 linear or branched C(O)-haloalkyl (e.g., C(O)—CF3), —C(O)NH2, C(O)NHR, C(O)N(R10)(R11), C2-C5 linear or branched, substituted or unsubstituted alkenyl (e.g., CH═C(Ph)2), C1-C5 linear or branched or C3-C8 cyclic haloalkyl, substituted or unsubstituted 3-8 membered heterocyclic ring, substituted or unsubstituted aryl (e.g., phenyl), or substituted or unsubstituted benzyl;
• or R2 and R3 are joined to form a C3-C8 substituted or unsubstituted, saturated or unsaturated, aliphatic (e.g. cyclopentyl, cyclohexyl), or aromatic (e.g. pyridine), carbocyclic or heterocyclic ring (e.g. pyrrolidine);
• R4 is H, substituted or unsubstituted C1-C10 linear or branched, or C3-C8 cyclic 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-C8 cycloalkyl), R8-(3-8 membered heterocyclic ring), CF3, CN, NO2, NH2, NHR, N(R)2, R8—N(R10)(Rn) (e.g. CH2—NH2), C(O)H, C1-C5 linear or branched C(O)-haloalkyl (e.g., C(O)—CF3), —C(O)NH2, C(O)NHR, C(O)N(R10)(R11), C2-C5 linear or branched, substituted or unsubstituted alkenyl (e.g., CH═C(Ph)2), C1-C5 linear or branched or C3-C8 cyclic haloalkyl, substituted or unsubstituted 3-8 membered heterocyclic ring, substituted or unsubstituted aryl (e.g., phenyl), or substituted or unsubstituted benzyl
• or R3 and R4 are joined to form a C3-C8 substituted or unsubstituted, saturated or unsaturated, aliphatic or aromatic, carbocyclic or heterocyclic ring (e.g. cyclopropyl), C═O or ═N—OH;
• R5 is 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 R2 and R5 are joined to form a substituted or unsubstituted 4-8 membered heterocyclic ring (e.g. pyrrolidine);
• R6 and R60 are 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-C8 cycloalkyl), 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), C(O)OH, —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-C5 linear 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-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl, benzyl), substituted or unsubstituted C3-C8 cycloalkyl (e.g., cyclopropyl, cyclopentyl), C2-C5 linear or branched, substituted or unsubstituted alkenyl (e.g., ethenyl), C2-C5 linear or branched, substituted or unsubstituted alkynyl (e.g., ethynyl, CC—CH2-cyclobutyl, CC—CF3), C1-C5 linear or branched or C3-C8 cyclic haloalkyl (e.g., CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)—CH(CH3)2), substituted or unsubstituted C1-C5 linear or branched or C3-C8 cyclic 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-C5 linear or branched thioalkoxy, C1-C5 linear 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,
• X1 is O, S, NH, NR (e.g., N—CH3), S═O, SO2;
• or X1 and R4 are joined to form a C4-C8 heterocyclic ring (e.g., pyrrolidine);
• X2, X3, X4, X5 are each independently C or N;
• X6 is O, NH, NR or CH2;
• G=X is C═O or SO2 or G(═X)—X6—R1 is a tetrazole moiety;
• R8 is [CH2]q
• wherein p is between 1 and 10;
• R9 is [CH]q, [C]q
• wherein q is between 2 and 10;
• R10 and R11 are each independently H, CN, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH3)), or S(O)2R;
• or R10 and R11 are joined to form a substituted or unsubstituted 3-8 membered heterocyclic ring;
• R is H, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C1-C5 linear 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 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.