Nematicide compounds, compositions, and methods of their making and use

A method of treating a plant or a growing media for a nematode, said method comprising:

• contacting a plant or a growing media with a compound of formula (I) having the following structure:
• or a stereoisomer, salt, oxide, or solvate thereof, wherein
• Y is a bond;
• —(CH2)n—;
• or —CH═;
• R1 is phenyl optionally substituted one or more times with halogen, CF3, alkoxy, C1-C6 alkyl, NO2, —OCF3, —OCF2H, —CN, alkylamine, or alkylthio;
• pyridine;
• pyrazine;
• carboxyalkyl;
• —CONH2;
• alkoxy;
• alkylsulfide;
• alkylamine;
• benzylpiperazine;
• H;
• CF3;
• and O- and Nα-protected amino acids comprising a carboxylate protected by a first protecting group and an amino group protected by a second protecting group;
• and
• X is O or S;
• Z is —(CH2)n—;
• R2 is selected from the group consisting of C1-C6 alkyl optionally substituted one or more times with halogen, alkoxy, or NH with an amine protecting group;
• C2-C10 alkenyl;
• phenyl optionally substituted one or more times with halogen or alkoxy;
• —COO(CH2)nCH3;
• —CO(CH2)nCH3;
• and an alcohol;
• and
• n is an integer selected from 0-3,
• to treat the plant or growing media for a nematode.

A compound of formula (II) having the following structure:

• or a stereoisomer, salt, oxide, or solvate thereof, wherein
• R3 and R4 are independently present or absent, and when present are independently halogen, alkoxy, or C1-C6 alkyl;
• X is O or S;
• and
• R5 is C1-C6 alkyl.

A compound of formula (III) having the following structure:

• or a stereoisomer, salt, oxide, or solvate thereof, wherein
• R6 is present or absent and when present is a halogen, alkoxy, or C1-C6 alkyl;
• R7 is selected from H, C1-C6 alkyl, alkoxy, and —COO(CH2)nCH3;
• X is S or O;
• R8 is —(CH2)nCOO(CH2)nCH3;
• and
• n is an integer between 0-3.

A method of making a compound formula (I) having the following structure:

• or a stereoisomer, salt, oxide, or solvate thereof, wherein
• Y is a bond;
• —(CH2)n—;
• or —CH═;
• R1 is phenyl optionally substituted one or more times with halogen, CF3, alkoxy, C1-C6 alkyl, NO2, —OCF3, —OCF2H, —CN, alkylamine, or alkylthio;
• pyridine;
• pyrazine;
• carboxyalkyl;
• —CONH2;
• alkoxy;
• alkylsulfide;
• alkylamine;
• benzylpiperazine;
• H;
• CF3;
• and O- and Nα-protected amino acids comprising a carboxylate protected by a first protecting group and an amino group protected by a second protecting group;
• and
• X is O or S;
• Z is —(CH2)n—;
• R2 is selected from the group consisting of C1-C6 alkyl optionally substituted one or more times with halogen, alkoxy, or NH with an amine protecting group;
• C2-C10 alkenyl;
• phenyl optionally substituted one or more times with halogen or alkoxy;
• —COO(CH2)nCH3;
• —CO(CH2)nCH3;
• and an alcohol;
• and
• n is an integer selected from 0-3,
• said method comprising:
• providing a starting material comprising an amidine, isourea, guanidine, or isothiourea molecule;
• reacting the starting material with carbon disulfide or an alkyl imidazole-1-carbodithioate molecule to form a dithiocarbamate compound;
• and
• converting the dithiocarbamate compound to a compound of formula (I).

A compound of formula (IV) having the following structure:

• or a stereoisomer, salt, oxide, or solvate thereof, wherein
• Y is a bond or C2-C10 alkylene;
• R1 is optional, and when present is phenyl optionally substituted at one or more positions with halogen, CF3, NO2, —CN, C1-C6 alkyl, C1-C6 alkoxy optionally substituted one or more times with halogen, C1-C6 alkylthio, —SCF3, C1-C6 alkylamine;
• benzodioxolyl optionally substituted one or more times with halogen;
• naphthalene;
• thiophene;
• indole optionally substituted one or more times with C1-C6 alkyl;
• and pyridine optionally substituted one or more times with halogen;
• and
• R2 and R3 are independently selected from C1-C8 alkyl and phenyl,
• with the following provisos:
• when Y is a bond and R1 is phenyl or phenyl substituted one time with a halogen, NO2 or MeO, R2 and R3 are not ethyl;
• when Y is a bond and R1 is naphthalene, R2 and R3 are not methyl;
• and
• when Y is C2 alkylene and R1 is phenyl, R2 and R3 are not ethyl.

A method of treating a plant or growing media for a nematode, said method comprising:

• contacting a plant or growing media with a compound of formula (IV) having the following structure:
• or a stereoisomer, salt, oxide, or solvate thereof, wherein
• Y is a bond or C2-C10 alkylene;
• R1 is optional, and when present is phenyl optionally substituted at one or more positions with halogen, CF3, NO2, —CN, C1-C6 alkyl, C1-C6 alkoxy optionally substituted one or more times with halogen, C1-C6 alkylthio, —SCF3, C1-C6 alkylamine;
• benzodioxolyl optionally substituted one or more times with halogen;
• naphthalene;
• thiophene;
• indole optionally substituted one or more times with C1-C6 alkyl;
• and pyridine optionally substituted one or more times with halogen;
• and
• R2 and R3 are independently selected from C1-C8 alkyl and phenyl to treat the plant or growing media for a nematode.

A method of treating a plant or growing media for a nematode, said method comprising:

• contacting a plant or growing media with a compound of formula (V) having the following structure:
• or a stereoisomer, salt, oxide, or solvate thereof, wherein
• R4 is selected from C1-C6 alkyl, alkoxy, CF3, and halogen and
• R5 is C1-C6 alkyl to treat the plant or growing media for a nematode.

A method of forming a ketene dithioacetal compound having a structure of formula (VI)

• said method comprising:
• providing a dimethyl methyl phosphonate compound having a structure of
• and
• reacting the dimethyl methyl phosphonate compound with a disulfide compound and an aldehyde to produce the compound of formula (VI), wherein R′, R″, and R′″ are any compatible substituent.