Herbicidal compounds and methods of use thereof

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

• wherein
• R1, R1′, R2, R2′ and R40 are each independently H, C1-C5 linear or branched, unsubstituted alkyl, methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl, benzyl, C(O)—R10, or C(O)—CH3;
• R3 is OH, or NH2;
• R4 is NH2, or OH;
• wherein if R3 is OH then R4 is NH2 and if R3 is NH2 then R4 is OH;
• wherein if R3 is OH and R4 is NH2, then n+m cannot be equal to 3;
• or R3 and R4 are joined together to form ring A, represented by the following structure:
• 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)—R10 (e.g., C(═CH2)—C(O)—OCH3, C(═CH2)—CN), substituted or unsubstituted alkyl sulfone (e.g., SO2—CH2-cyclopentyl), substituted or unsubstituted aryl (e.g., phenyl), substituted or unsubstituted heteroaryl (e.g., pyridine (2, 3, and 4-pyridine);
• R8 is [CH2]p
• wherein p is between 1 and 10;
• R10 is H, CN, C1-C5 linear or branched alkyl, C(O)R, or S(O)2R;
• R is C1-C5 linear or branched alkyl, C1-C5 linear or branched alkoxy, phenyl, aryl or heteroaryl;
• m is 1 or 2;
• n is 0, 1, 2 or 3;
• X1 is S, O, or CH2;
• X2 is S, O, or CH2;
• X3 is O, NH or N—R50;
• R50 is H or C1-C5 linear or branched, substituted or unsubstituted alkyl;
• or its agrochemically acceptable salt, stereoisomer, tautomer, hydrate, N-oxide, reverse amide analog, isotopic variant (e.g., deuterated analog), or any combination thereof;
• or a compound represented by the structure of formula X(a):
• wherein
• R5 is H, C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, CH2SH, ethyl, butyl, CH2—CCH, iso-propyl, CH2—C(O)—OCH3), C2-C5 linear or branched, substituted or unsubstituted alkenyl, C2-C5 linear or branched, substituted or unsubstituted alkynyl (e.g., CCH, CH2—CCH), C1-C5 linear or branched haloalkyl (e.g., CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)—CH(CH3)2), R8-aryl (e.g., CH2-Ph), C(═CH2)—R10 (e.g., C(═CH2)—C(O)—OCH3, C(═CH2)—CN), substituted or unsubstituted aryl (e.g., phenyl), substituted or unsubstituted heteroaryl (e.g., pyridine (2, 3, and 4-pyridine);
• R8 is [CH2]p
• wherein p is between 1 and 10;
• R10 is H, CN, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH3)), or S(O)2R;
• R is H, 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;
• X1 is S, O, CH2, CH(R) or C(R)2;
• wherein if X1 is CH2, then R5 cannot be H;
• n is 2;
• m is 0;
• m is an integer number between 1 and 3;
• or its agrochemically acceptable salt, stereoisomer, tautomer, hydrate, N-oxide, reverse amide analog, isotopic variant (e.g., deuterated analog), or any combination thereof;
• or a compound represented by the structure of formula X(c):
• wherein
• R5 is H, C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, CH2SH, ethyl, butyl, CH2—CCH, iso-propyl, CH2—C(O)—OCH3), C2-C5 linear or branched, substituted or unsubstituted alkenyl, C2-C5 linear or branched, substituted or unsubstituted alkynyl (e.g., CCH, CH2—CCH), C1-C5 linear or branched haloalkyl (e.g., CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)—CH(CH3)2), R8-aryl (e.g., CH2-Ph), C(═CH2)—R10 (e.g., C(═CH2)—C(O)—OCH3, C(═CH2)—CN), substituted or unsubstituted aryl (e.g., phenyl), substituted or unsubstituted heteroaryl (e.g., pyridine (2, 3, and 4-pyridine);
• R8 is [CH2]p
• wherein p is between 1 and 10;
• R10 is H, CN, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH3)), or S(O)2R;
• R is H, 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;
• X1 is S, O, CH2, CH(R) or C(R)2;
• X2 is O, CH2, CH(R) or C(R)2;
• n is an integer number between 1 and 2;
• m is an integer number between 1 and 3;
• or its agrochemically acceptable salt, stereoisomer, tautomer, hydrate, N-oxide, reverse amide analog, isotopic variant (e.g., deuterated analog), or any combination thereof;
• or a compound represented by the structure of formula X(d):
• wherein
• R5 is H, C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, CH2SH, ethyl, butyl, CH2—CCH, iso-propyl, CH2—C(O)—OCH3), C2-C5 linear or branched, substituted or unsubstituted alkenyl, C2-C5 linear or branched, substituted or unsubstituted alkynyl (e.g., CCH, CH2—CCH), C1-C5 linear or branched haloalkyl (e.g., CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)—CH(CH3)2), R8-aryl (e.g., CH2-Ph), C(═CH2)—R10 (e.g., C(═CH2)—C(O)—OCH3, C(═CH2)—CN), substituted or unsubstituted aryl (e.g., phenyl), substituted or unsubstituted heteroaryl (e.g., pyridine (2, 3, and 4-pyridine);
• R8 is [CH2]p
• wherein p is between 1 and 10;
• R10 is H, CN, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH3)), or S(O)2R;
• R is H, 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;
• X2 is S, O, CH2, CH(R) or C(R)2;
• n is an integer number between 1 and 2;
• m is 1 or 3;
• or its agrochemically acceptable salt, stereoisomer, tautomer, hydrate, N-oxide, reverse amide analog, isotopic variant (e.g., deuterated analog), or any combination thereof;
• or a compound, represented by any one of the following structures:
• Compound
• Structure
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• or its agrochemically acceptable salt, stereoisomer, tautomer, hydrate, N-oxide, reverse amide analog, isotopic variant (e.g., deuterated analog), or any combination thereof.

An herbicidal compound, represented by the structure of formula I(ga):

• wherein
• CA and CB are both chiral carbon centers, or CA and CB together with R3 and R4 are joined to form ring A, represented by the following structure:
• R1, R1′, R2, R2′ and R40 are each independently H, C1-C5 linear or branched, unsubstituted alkyl, methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl, benzyl, C(O)—R10, or C(O)—CH3;
• R3 is OH, SH, NH2, NHNH2, NHR, N(R)2, NHC(O)OBz, —NHC(O)—R10, NHC(O)CH3, C1-C5 linear or branched, substituted or unsubstituted alkyl, methyl, ethyl, propyl, iso-propyl, t-Bu, iso-butyl, pentyl, substituted or unsubstituted C3-C8 cycloalkyl, C1-C5 linear or branched or C3-C8 cyclic haloalkyl, C1-C5 linear or branched or C3-C8 cyclic alkoxy, substituted or unsubstituted C3-C8 heterocyclic ring, or substituted or unsubstituted aryl;
• R4 is NH2, NHNH2, N(R)2, —NHC(O)—R10, NHC(O)H, NHC(O)CH3, C1-C5 linear or branched, substituted or unsubstituted alkyl, C1-C5 linear or branched or C3-C8 cyclic haloalkyl, C1-C5 linear or branched or C3-C8 cyclic alkoxy, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C3-C8 heterocyclic ring, or substituted or unsubstituted aryl;
• or R3 and R4 are joined together to form ring A as described above;
• wherein R3 and R4 cannot both be NH2, and
• wherein if R3 is OH and R4 is NH2, then n+m cannot be equal to 3;
• R5 is H, C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, CH2SH, ethyl, butyl, CH2—CCH, 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)—R10 (e.g., C(═CH2)—C(O)—OCH3, C(═CH2)—CN), substituted or unsubstituted alkyl sulfone (e.g., SO2—CH2-cyclopentyl), substituted or unsubstituted aryl (e.g., phenyl), substituted or unsubstituted heteroaryl (e.g., pyridine (2, 3, and 4-pyridine);
• R8 is [CH2]p
• wherein p is between 1 and 10;
• R10 and Ru are each independently H, CN, C1-C5 linear or branched alkyl, C(O)R, or S(O)2R;
• or R10 and R11 are joined to form a substituted or unsubstituted C3-C8 heterocyclic ring;
• R is C1-C5 linear or branched alkyl, C1-C5 linear or branched alkoxy, phenyl, aryl or heteroaryl, or two gem R substituents are joined together to form a 5 or 6 membered heterocyclic ring;
• m is 1 or 2;
• n is 0, 1, 2 or 3;
• X1 is S, O, or CH2;
• X2 is S, O, or CH2;
• X3 is O, NH or N—R50;
• R50 is H or C1-C5 linear or branched, substituted or unsubstituted alkyl;
• or its agrochemically acceptable salt, stereoisomer, tautomer, hydrate, N-oxide, reverse amide analog, isotopic variant (e.g., deuterated analog), or any combination thereof;
• or an herbicidal compound represented by the structure of formula X(b):
• wherein
• R5 is H, C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, CH2SH, ethyl, butyl, CH2—CCH, iso-propyl, CH2—C(O)—OCH3), C2-C5 linear or branched, substituted or unsubstituted alkenyl, C2-C5 linear or branched, substituted or unsubstituted alkynyl (e.g., CCH, CH2—CCH), C1-C5 linear or branched haloalkyl (e.g., CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)—CH(CH3)2), R8-aryl (e.g., CH2-Ph), C(═CH2)—R10 (e.g., C(═CH2)—C(O)—OCH3, C(═CH2)—CN), substituted or unsubstituted aryl (e.g., phenyl), substituted or unsubstituted heteroaryl (e.g., pyridine (2, 3, and 4-pyridine);
• R8 is [CH2]p
• wherein p is between 1 and 10;
• R10 is H, CN, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH3)), or S(O)2R;
• R is H, 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;
• X1 is S, O, CH2, CH(R) or C(R)2;
• X2 is S, O, CH2, CH(R) or C(R)2;
• n is an integer number between 0 and 2;
• m is an integer number between 1 and 3;
• or its agrochemically acceptable salt, stereoisomer, tautomer, hydrate, N-oxide, reverse amide analog, isotopic variant (e.g., deuterated analog), or any combination thereof;
• or an herbicidal compound represented by the structure of formula X(c):
• wherein
• R5 is H, C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, CH2SH, ethyl, butyl, CH2—CCH, iso-propyl, CH2—C(O)—OCH3), C2-C5 linear or branched, substituted or unsubstituted alkenyl, C2-C5 linear or branched, substituted or unsubstituted alkynyl (e.g., CCH, CH2—CCH), C1-C5 linear or branched haloalkyl (e.g., CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)—CH(CH3)2), R8-aryl (e.g., CH2-Ph), C(═CH2)—R10 (e.g., C(═CH2)—C(O)—OCH3, C(═CH2)—CN), substituted or unsubstituted aryl (e.g., phenyl), substituted or unsubstituted heteroaryl (e.g., pyridine (2, 3, and 4-pyridine);
• R8 is [CH2]p
• wherein p is between 1 and 10;
• R10 is H, CN, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH3)), or S(O)2R;
• R is H, 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;
• X1 is S, O, CH2, CH(R) or C(R)2;
• X2 is S, O, CH2, CH(R) or C(R)2;
• n is an integer number between 0 and 2;
• m is an integer number between 1 and 3;
• or its agrochemically acceptable salt, stereoisomer, tautomer, hydrate, N-oxide, reverse amide analog, isotopic variant (e.g., deuterated analog), or any combination thereof;
• or an herbicidal compound, represented by any one of the following structures:
• Compound
• Structure
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• or its agrochemically acceptable salt, stereoisomer, tautomer, hydrate, N-oxide, reverse amide analog, isotopic variant (e.g., deuterated analog), or any combination thereof.

A method for controlling the growth of undesired plants, comprising applying to the undesired plants or a locus comprising them, an effective amount of a compound represented by the structure of formula X(a):

• wherein
• R5 is H, C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, CH2SH, ethyl, butyl, CH2—CCH, iso-propyl, CH2—C(O)—OCH3), C2-C5 linear or branched, substituted or unsubstituted alkenyl, C2-C5 linear or branched, substituted or unsubstituted alkynyl (e.g., CCH, CH2—CCH), C1-C5 linear or branched haloalkyl (e.g., CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)—CH(CH3)2), R8-aryl (e.g., CH2-Ph), C(═CH2)—R10 (e.g., C(═CH2)—C(O)—OCH3, C(═CH2)—CN), substituted or unsubstituted aryl (e.g., phenyl), substituted or unsubstituted heteroaryl (e.g., pyridine (2, 3, and 4-pyridine);
• R8 is [CH2]p
• wherein p is between 1 and 10;
• R10 is H, CN, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH3)), or S(O)2R;
• R is H, 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;
• X1 is S, O, CH2, CH(R) or C(R)2;
• n and o are each independently an integer number between 0 and 2;
• m is an integer number between 1 and 3;
• or its agrochemically acceptable salt, stereoisomer, tautomer, hydrate, N-oxide, reverse amide analog, isotopic variant (e.g., deuterated analog), or any combination thereof;
• or of a compound represented by the structure of formula X(d):
• wherein
• R5 is H, C1-C5 linear or branched, substituted or unsubstituted alkyl (e.g., methyl, CH2SH, ethyl, butyl, CH2—CCH, iso-propyl, CH2—C(O)—OCH3), C2-C5 linear or branched, substituted or unsubstituted alkenyl, C2-C5 linear or branched, substituted or unsubstituted alkynyl (e.g., CCH, CH2—CCH), C1-C5 linear or branched haloalkyl (e.g., CF3, CF2CH3, CH2CF3, CF2CH2CH3, CH2CH2CF3, CF2CH(CH3)2, CF(CH3)—CH(CH3)2), R8-aryl (e.g., CH2-Ph), C(═CH2)—R10 (e.g., C(═CH2)—C(O)—OCH3, C(═CH2)—CN), substituted or unsubstituted aryl (e.g., phenyl), substituted or unsubstituted heteroaryl (e.g., pyridine (2, 3, and 4-pyridine);
• R8 is [CH2]p
• wherein p is between 1 and 10;
• R10 is H, CN, C1-C5 linear or branched alkyl (e.g., methyl, ethyl), C(O)R (e.g., C(O)(OCH3)), or S(O)2R;
• R is H, 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;
• X2 is S, O, CH2, CH(R) or C(R)2;
• n is an integer number between 0 and 2;
• m is an integer number between 1 and 3;
• or its agrochemically acceptable salt, stereoisomer, tautomer, hydrate, N-oxide, reverse amide analog, isotopic variant (e.g., deuterated analog), or any combination thereof;
• or an agrochemical composition thereof, under conditions effective to control the growth of the undesired plants, in particular the growth of weeds, in crops of useful plants compound.