Classifications

• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
  • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01G—HORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
  • A01G7/00—Botany in general
  • A01G7/06—Treatment of growing trees or plants, e.g. for preventing decay of wood, for tingeing flowers or wood, for prolonging the life of plants
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
  • A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
  • A01N31/14—Ethers
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
  • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
  • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
  • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
  • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
  • A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
  • A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
  • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
  • A01N43/46—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom rings with more than six members
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
  • A01N59/26—Phosphorus; Compounds thereof
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
  • A01P13/00—Herbicides; Algicides
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
  • A01P21/00—Plant growth regulators
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
  • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D213/61—Halogen atoms or nitro radicals
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D213/72—Nitrogen atoms
  • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D213/72—Nitrogen atoms
  • C07D213/76—Nitrogen atoms to which a second hetero atom is attached
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
  • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
  • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
  • C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
  • C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
  • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
  • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
  • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
  • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
  • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
  • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
  • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D333/28—Halogen atoms
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  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
  • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
  • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
  • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D333/30—Hetero atoms other than halogen
  • C07D333/36—Nitrogen atoms

Definitions

• the invention relates to novel chemical compounds having herbicidal activity, process for their manufacture and their use in crop protection.
• Amino acids and their derivatives are involved in a plethora of cellular reactions and therefore they influence on a number of physiological processes such as plant growth and development, intracellular pH control, generation of metabolic energy or redox power, and resistance to both abiotic and biotic stress. Pools of all amino acids are induced during stress. For example, proline significantly increases in stress response in several plants and considered as a compatible osmolyte. In addition, branched-chain amino acids are also dramatically induced during various stress conditions.
• New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around railroad tracks, storage tanks and industrial storage areas. Identifying new compounds having herbicidal activity, which are more effective, less costly and environmentally safe, remains long and unmet need.
• the invention provides an agricultural composition comprising a compound having the structure or a salt thereof, wherein:
• A is cyclopentadiene, benzene and indene scaffold comprising from 1 to 4 heteroatoms; wherein each of the heteroatoms is independently selected from the group consisting of N, S, Se, and 0; and wherein one or more of the carbon atoms of the ring are optionally chemically attached to at least one of the groups consisting of: -SO2CF3, -O-SO2CF3, -NR.
• Z is -C00H, C00-, OH, -0-R, COOR with saturated or non-saturated alcohol residues with straight, branched, cyclic, aromatic or heteroaromatic chain;-0-(CH2CH2O) n R (n3l); -0-(CHMeCH20) n R (n3l)); sulfonyl group, carbamoyl group,primary amine, secondary amine, tertiary amine, carboxamide,-NR-O-R, -0- NR2, hydrazine, -NH-COR, and methanimidamide moiety or a salt thereof; wherein R is selected from H, substituted or non-substituted alkyl, and substituted or non-substituted aryl group; and, wherein the composition comprises at least one agriculturally acceptable carrier.
• the invention further provides a method of controlling undesired plant growth, comprising applying to the locus of the undesired plant growth a herbicidally effective amount of a compound having the structure or a salt thereof, wherein:
• A is cyclopentadiene, benzene and indene scaffold comprising from 1 to 4 heteroatoms; wherein each of the heteroatoms is independently selected from the group consisting of N, S, Se, and 0; and wherein one or more of the carbon atoms of the ring are optionally chemically attached to at least one of the groups consisting of: -SO2CF3, -O-SO2CF3,-NR.
• Z is -COOH, COO-, OH, -O-R, COOR with saturated or non-saturated alcohol residues with straight, branched, cyclic, aromatic or heteroaromatic chain;-0-(CH2CH2O) n R (n3l);-0-(CHMeCH20) n R (n3l)); sulfonyl group, carbamoyl group,primary amine, secondary amine, tertiary amine, carboxamide,-NR-O-R, -0- NR2, hydrazine, -NH-COR, and methanimidamide moiety or a salt thereof; wherein R is selected from H, substituted or non-substituted alkyl, and substituted or non-substituted aryl group.
• the invention further provides a method of controlling undesired plant growth comprising applying to the locus of the undesired plant growth: a.
• a first herbicide having the structure or a salt thereof, wherein:
• Z is -COOH, COO-, OH, -O-R, COOR with saturated or non- saturated alcohol residues with straight, branched, cyclic, aromatic or heteroaromatic chain;-0-(CH2CH2O) n R (n3l);-0- (CHMeCH20) n R (n3l)); sulfonyl group, carbamoyl group,primary amine, secondary amine, tertiary amine, carboxamide,-NR-O-R, -O-NR2, hydrazine, -NH-COR, and methanimidamide moiety or a salt thereof; wherein R is selected from H, substituted or non- substituted alkyl, and substituted or non-substituted aryl group, b.
• a second herbicide to thereby effectively control the undesired plant growth.
• the invention further provides a composition for controlling undesired plant growth comprising a mixture of: a. a compound having the structure or a salt thereof, wherein:
• Z is -COOH, COO-, OH, -O-R, COOR with saturated or non- saturated alcohol residues with straight, branched, cyclic, aromatic or heteroaromatic chain;-0-(CH2CH2O) n R (n3l);-0- (CHMeCH 2 0) n R (n3l)); sulfonyl group, carbamoyl group,primary amine, secondary amine, tertiary amine, carboxamide,-NR-O-R, -O-NR2, hydrazine, -NH-COR, and methanimidamide moiety or a salt thereof; wherein R is selected from H, substituted or non-substituted alkyl, and substituted or non-substituted aryl group; b.
• At least one herbicide selected from the group consisting of atrazine, terbuthylazine, (S)-metolachlor, metolachlor, terbutryn, simazine, dimethenamid, (S)-dimethenamid, flufenacet, acetochlor, alachlor, isoxaflutole, isoxachlortole, mesotrione, sulcotrione, metosulam, flumetsulam, pendimethalin, bromoxynil, bentazone, carfentrazone-ethyl, clomazone, nicosulfuron, rimsulfuron, halosulfuron-methyl, metribuzin, flumiclorac-pentyl , prosulfuron, primisulfuron-methyl, dicamba, fluthiacet- methyl, pyridate, 2,4-D, clopyralide, diflufenzopyr, fluroxypyr, MCPA,
• the invention further provides a composition for controlling undesired plant growth comprising a mixture of: a. a compound having the structure or a salt thereof, wherein:
• T is unsubstituted or substituted methylene group with one or two halide atoms, oxygen, -SO2CF3, -O-SO2CF3, -NR3+ , -
• Z is -C00H, C00-, OH, -0-R, COOR with saturated or non- saturated alcohol residues with straight, branched, cyclic, aromatic or heteroaromatic chain;-0-(CH2CH2O) n R (n3l);-0-(CHMeCH 2 0) n R (n3l)); sulfonyl group, carbamoyl group,primary amine, secondary amine, tertiary amine, carboxamide,-NR-O-R, -O-NR2, hydrazine, -NH-COR, and methanimidamide moiety or a salt thereof; wherein R is selected from H, substituted or non- substituted alkyl, and substituted or non-substituted aryl group; b. at least one plant growth regulator; and, c. at least one agriculturally acceptable carrier.
• the invention provides an agricultural composition comprising a compound or a salt thereof having the structure or a salt thereof, wherein:
• Z is -COOH, COO-, OH, -O-R, COOR with saturated or non-saturated alcohol residues with straight, branched, cyclic, aromatic or heteroaromatic chain;-0-(CH2CH2O) n R (n3l); -0-(CHMeCH20) n R (n3l)); sulfonyl group, carbamoyl group,primary amine, secondary amine, tertiary amine, carboxamide,-NR-O-R, -0- NR2, hydrazine, -NH-COR, and methanimidamide moiety or a salt thereof; wherein R is selected from H, substituted or non-substituted alkyl, and substituted or non-substituted aryl group; and, wherein the composition comprises at least one agriculturally acceptable carrier.
• A is heterocyclic aromatic ring substituted with one or more Electron Withdrawing Group (EWG).
• EWG Electron Withdrawing Group
• the term “electron withdrawing group” (EWG) refers, without limitation, to an atom or a group that draws electron density from neighboring atoms or aromatic ring, usually by resonance and/or inductive effects.
• substituted ammonium groups such as, without limitation, -NR3+ (R is alkyl/s or H); nitro and nitroso groups, -N02, -
• Z may be, without limitation, carboxyl or salts thereof -COOH or C00- , hydroxyl -OH, ether -0-R, ester COOR with saturated or non- saturated alcohol groups with straight, branched, cyclic chain or aromatic/heteroaromatic chain, ethylene- and polyethylene glycol -0- (CH2CH2O) n R (n3l, R is H or alkyl), propylene and polypropylene glycol -0- (CHMeCfkO) n R (n >1, R is H or alkyl), phosphates (substituted and non-substituted), sulfate/sulfonyl, carbamoyl group that consists of primary, secondary, and tertiary amide substituted with straight, branched, cyclic aliphatic chain, cyclic aromatic/heteroaromatic chain, ethylene glycol and polyethylene glycol (as above), propylene
• Z might be, without limitation: n -0-7
• the above composition comprises a compound having the structure or a salt thereof, wherein each R 1 and R 2 is independently selected from H, Cl; Br; I; -CF3; and -CN, where at least one of them is not H; R 3 is H, -COH, -CN, 0 or F; and R 4 is selected from H, saturated or non-saturated aliphatic straight, branched, cyclic or aromatic chain; ethylene glycol; polyethylene glycol; propylene glycol, polypropylene glycol, ethylpyridine, ethylbenzene, 1-(bromophenyl)ethan-l-one, 1- (lH-inden-3- yl)ethan-l-one, 1-(2,3-dihydro-lH-inden-l-yl)ethan-l-one; 1- (2,3-dihydro-lH-inden-l-yl)propan-l-one; and 1- (lH-inden-3-
• R 1 and R 2 is selected from H, Cl; Br; I; -CF3; and -CN where at least one of them is not H;
• R 3 is H, -COH, -CN, 0 or F;
• R 4 is selected from H, saturated or non-saturated aliphatic straight, branched, cyclic or aromatic chain; ethylene glycol; polyethylene glycol; propylene glycol, polypropylene glycol, ethylpyridine, ethylbenzene, 1-(bromophenyl)ethan-l-one, 1-(1H- inden-3-yl)ethan-l-one, 1-(2,3-dihydro-lH-inden-l-yl )ethan-l- one; 1-(2,3-dihydro-lH-inden-l-yl)propan-l-one; and 1-(1H- inden-3-yl)propan-l-one .
• the above composition comprises a compound having the structure
• R 1 and R 2 is selected from H, Cl; Br; I; -CF3; and -CN where at least one of them is not H;
• R 3 is H, -COH, -CN, 0 or F;
• R 4 is selected from H, saturated or non-saturated aliphatic straight, branched, cyclic or aromatic chain; ethylene glycol; polyethylene glycol; propylene glycol, polypropylene glycol, ethylpyridine, ethylbenzene, 1-(bromophenyl)ethan-l-one, 1-(1H- inden-3-yl)ethan-l-one, 1-(2,3-dihydro-lH-inden-l-yl )ethan-l- one; 1-(2,3-dihydro-lH-inden-l-yl)propan-l-one; and 1-(1H- inden-3-yl)propan-l-one .
• the above composition comprises a compound having the structure wherein R 1 is selected from Cl; Br; I; -CF3; R 2 and R 3 is H or F; and R 4 is selected from H, saturated or non-saturated aliphatic straight, branched, cyclic or aromatic chain; ethylene glycol; polyethylene glycol; propylene glycol, polypropylene glycol, ethylpyridine, ethylbenzene, 1-(bromophenyl)ethan-l-one, 1-(1H- inden-3-yl)ethan-l-one, 1-(2,3-dihydro-lH-inden-l-yl )ethan-l- one; 1-(2,3-dihydro-lH-inden-l-yl)propan-l-one; and 1-(1H- inden-3-yl)propan-l-one .
• R 1 is selected from Cl; Br; I; -CF3; R 2 and R 3 is H or F; and R 4
• the above composition comprises a compound selected from (2-bromo-l,3-thiazol-4 yl) (difluoro)acetic acid; difluoro[2-(trifluoromethyl) -1,3- thiazol-4-yl]acetic acid; (2-cyano-l,3-thiazol-4-yl)(di fluoro)acetic acid; (2-chloro-l,3-thiazol-4-yl)(difluoro)acetic acid; 2-[2-(2-ethoxyethoxy)ethoxy]ethyl (2-chloro-l,3-thiazol- 4-yl) (difluoro)acetate; 2-(2-bromophenyl)-2-oxoethyl (2-chloro- 1,3-thiazol-4-yl )(difluoro)acetate; 2-(2,7-methyl-2,3-dihydro- lH-inden-l-yl)-2
• the non limiting list of compounds or agriculturally acceptable salts includes :
• the agricultural composition further comprises at least one crop protection agent.
• the at least one crop protection agent is selected from the group consisting of fungicide, insecticide, herbicide, and plant growth regulator.
• the crop protection agent is herbicide.
• the crop protection agent is plant growth regulator.
• the at least one crop protection agent is selected from the group consisting of atrazine, terbuthylazine, (S)-metolachlor, metolachlor, terbutryn, simazine, dimethenamid, (S)-dimethenamid, flufenacet, acetochlor, alachlor, isoxaflutole, isoxachlortole, mesotrione, sulcotrione, metosulam, flumetsulam, pendimethalin, bromoxynil, bentazone, carfentrazone-ethyl, clomazone, nicosulfuron, rimsulfuron, halosulfuron-methyl, metribuzin, flumiclorac- pentyl, prosulfuron, primisulfuron-methyl, dicamba, fluthiacet- methyl, pyridate, 2,4-D, clopyralide, diflufenzopyr, fluroxypyr
• 2,4-DP bifenox, flamprop-M, imazamethabenz-methyl, ioxynil, tralkoxydim, fluoroglycofen-ethyl, methabenzthiazuron, isoxaben, prosulfocarb, difenzoquat-metilsulfate, pretilachlor, cinosulfuron, fenclorim, bensulfuron-methyl, imazosulfuron, pyrazosulfuron-ethyl, azimsulfuron, esprocarb, mefenacet, molinate, propanil, pyrazolate, cyhalofop-butyl, bispyribac- sodium, pyriminobac-methyl, cafenstrole, oxadiargyl, oxadiazon, bromobutide, MY-100, dymron, NB 061, MK243, HW-52, AC 014, ametryn,
• the invention provides a method of controlling undesired plant growth comprising applying to the locus of said undesired plant growth the agricultural composition according to one or more embodiments of the above composition .
• the invention provides a method of controlling undesired plant growth comprising applying to the locus of the undesired plant growth a herbicidally effective amount of a compound having the structure or a salt thereof, wherein:
• T is unsubstituted or substituted methylene group with one or two halides, oxygen, -SO2CF3, -O-SO2CF3,-NR 3 + , -SO2R,-CoN, -
• Z is -COOH, COO-, OH, -O-R, COOR with saturated or non-saturated alcohol residues with straight, branched, cyclic, aromatic or heteroaromatic chain;-0-(CH2CH2O) n R (n3l);-0-(CHMeCH 2 0) n R (n3l)); sulfonyl group, carbamoyl group,primary amine, secondary amine, tertiary amine, carboxamide,-NR-O-R, -0- NR2, hydrazine, -NH-COR, and methanimidamide moiety or a salt thereof; wherein R is selected from H, substituted or non-substituted alkyl, and substituted or non-substituted aryl group.
• Z might be selected, without limitation, from the group including:
• the unlimiting list of compounds, or agriculturally acceptable salts includes :
• the non ⁇ limiting list of compounds or agriculturally acceptable salts includes :
• the method further comprises applying to the locus of the undesired plant growth at least one crop protection agent.
• the crop protection agent is selected from the group consisting of herbicide, fungicide, insecticide and plant growth regulator.
• the crop protection agent is herbicide.
• the crop protection agent is amino acid synthesis inhibitor herbicide.
• the non-limiting list of amino acid synthesis inhibitor herbicides of the invention includes: sulfonylurea herbicide, imidazolinone herbicide, sulfonamide herbicide, amino acid derivatives, imazamox, imazapic, imazethapyr, imazaquin, imazapyr and imazamethabenz, Chlorimuron, Primisulfuron, Thifensulfuron, Triasulfuron, Nicosulfuron, Metsulfuron, Tribenuron, Rimsulfuron, Triflusulfuron, glyphosate or any combination thereof.
• the crop protection agent is a plant growth regulator.
• the non-limiting list of plant growth regulators of the invention includes: dicamba, 2,4-D, clopyralid and fluroxypyr.
• the invention provides a method of controlling undesired plant growth comprising applying to the locus of the undesired plant growth: a. a first herbicide having the structure
• A is cyclopentadiene, benzene and indene scaffold comprising from 1 to 4 heteroatoms; wherein each of the heteroatoms is independently selected from the group consisting of N, S, Se, and 0; and wherein one or more of the carbon atoms of the ring are optionally chemically attached to at least one of the groups consisting of: -SO2CF3, -O-SO2CF3,-NR. 3 + , -SO2R, -CoN, -CX 3 , CX2R-COX, -CHO, -COR, -CO2R, -CONH2, -CONHR, -
• Z is -COOH, COO-, OH, -O-R, COOR with saturated or non- saturated alcohol residues with straight, branched, cyclic, aromatic or heteroaromatic chain;-0-(CH2CH2O) n R (n3l);-0-(CHMeCH 2 0) n R (n3l)); sulfonyl group, carbamoyl group,primary amine, secondary amine, tertiary amine, carboxamide,-NR-O-R, -O-NR2, hydrazine, -NH-COR, and methanimidamide moiety or a salt thereof; wherein R is selected from H, substituted or non-substituted alkyl, and substituted or non-substituted aryl group; b. a second herbicide, to effectively control the undesired plant growth. to thereby effectively control the undesired plant growth.
• Z might be, without limitation:
• the second herbicide is amino acid synthesis inhibitor herbicide.
• the second herbicide is selected from the group consisting of sulfonylurea herbicide, imidazolinone herbicide, sulfonamide herbicide, and amino acid derivative.
• the non limiting list of the second herbicides of the invention includes: imazamox, imazapic, imazethapyr, imazaquin, imazapyr, imazamethabenz, Chlorimuron, Primisulfuron, Thifensulfuron, Triasulfuron, Nicosulfuron, Metsulfuron, Tribenuron, Rimsulfuron, Triflusulfuron, Glyphosate, atrazine, terbuthylazine, (S)-metolachlor, metolachlor, terbutryn, simazine, dimethenamid, (S)-dimethenamid, flufenacet, acetochlor, alachlor, isoxaflutole, isoxachlortole, mesotrione, sulcotrione, metosulam, flumetsulam, pendimethalin, bromoxynil, bentazone, carf
• 2,4-DP bifenox, flamprop-M, imazamethabenz-methyl, ioxynil, tralkoxydim, fluoroglycofen-ethyl, methabenzthiazuron, isoxaben, prosulfocarb, difenzoquat-metilsulfate, pretilachlor, cinosulfuron, fenclorim, bensulfuron-methyl, imazosulfuron, pyrazosulfuron-ethyl, azimsulfuron, esprocarb, mefenacet, molinate, propanil, pyrazolate, cyhalofop-butyl, bispyribac- sodium, pyriminobac-methyl, cafenstrole, oxadiargyl, oxadiazon, bromobutide, MY-100, dymron, NB 061, MK243, HW-52, AC 014, ametryn,
• the method further comprises applying a third herbicide or a plant growth regulator .
• the invention provides a composition for controlling undesired plant growth comprising a mixture of: a. a compound or a salt thereof having the structure
• Z is -COOH, COO-, OH, -O-R, COOR with saturated or non- saturated alcohol residues with straight, branched, cyclic, aromatic or heteroaromatic chain;-0-(CH2CH2O) n R (n3l);-0- (CHMeCH 2 0) n R (n3l)); sulfonyl group, carbamoyl group,primary amine, secondary amine, tertiary amine, carboxamide,-NR-O-R, -O-NR2, hydrazine, -NH-COR, and methanimidamide moiety or a salt thereof; wherein R is selected from H, substituted or non-substituted alkyl, and substituted or non-substituted aryl group; b.
• At least one herbicide selected from the group consisting of atrazine, terbuthylazine, (S)-metolachlor, metolachlor, terbutryn, simazine, dimethenamid, (S)-dimethenamid, flufenacet, acetochlor, alachlor, isoxaflutole, isoxachlortole, mesotrione, sulcotrione, metosulam, flumetsulam, pendimethalin, bromoxynil, bentazone, carfentrazone-ethyl, clomazone, nicosulfuron, rimsulfuron, halosulfuron-methyl, metribuzin, flumiclorac-pentyl , prosulfuron, primisulfuron-methyl, dicamba, fluthiacet- methyl, pyridate, 2,4-D, clopyralide, diflufenzopyr, fluroxypyr, MCPA,
• Z is -C00H, C00-, OH, -0-R, COOR with saturated or non- saturated alcohol residues with straight, branched, cyclic, aromatic or heteroaromatic chain;-0-(CH2CH2O) n R (n3l);-0-(CHMeCH20) n R (n3l)); sulfonyl group, carbamoyl group,primary amine, secondary amine, tertiary amine, carboxamide,-NR-O-R, -O-NR2, hydrazine, -NH-COR, and methanimidamide moiety or a salt thereof; wherein R is selected from H, substituted or non-substituted alkyl, and substituted or non-substituted aryl group; b. at least one plant growth regulator; and c. at least one agriculturally acceptable carrier.
• method of controlling amino acid content in a plant or a plant part thereof comprising applying an effective amount of the agricultural composition according to the above embodiments of the invention.
• the invention provides a method of controlling amino acid content in a plant or a plant part thereof, comprising applying an effective amount of the agricultural composition according to the above embodiments of the invention.
• the invention provides a method of controlling plant growth comprising applying to the plant or a plant part thereof, an effective amount of the agricultural composition according to the above embodiments of the invention.
• the invention provides a method of controlling growth of plants at least partially resistant to herbicides selected from the HPAC 9 group (Inhibitors of EPSP synthesis), 2 (Acetolactate Synthase (ALS) inhibitors), and 4 (Plant growth regulators or synthetic auxins), comprising applying to the plant or a plant part thereof, an effective amount of the agricultural composition according to the above embodiments of the invention.
• herbicides selected from the HPAC 9 group (Inhibitors of EPSP synthesis), 2 (Acetolactate Synthase (ALS) inhibitors), and 4 (Plant growth regulators or synthetic auxins
• the invention provides an agricultural composition comprising one or more compounds listed in Tables 2, 3, 4 and 5, and at least one agriculturally acceptable carrier.
• the invention provides method of controlling undesired plant growth comprising applying one or more compounds listed in Tables 2, 3, 4 and 5.
• the invention provides method of controlling undesired plant growth comprising applying an agricultural composition comprising one or more compounds listed in Tables 2, 3, 4 and 5, and at least one agriculturally acceptable carrier.
• Step A 4-(2-aminoethyl)thiazol-2-amine dihydrochloride (5 g, 23.3 mmol) was suspended in DCM and cooled to 0°C, following by the consequent addition of TEA (7g, 70 mmol) and acetic anhydride (2.4g, 24 mmol) in a dropwise manner. After the reaction was complete, the mixture was evaporated to dryness and re ⁇ evaporated with toluene 3 times to give crude N- (2-(2- aminothiazol-4-yl )ethyl)acetamide (4.5g, crude) which was used in the next step without purification.
• Step B N-(2-(2-aminothiazol-4-yl)ethyl)acetamide (4.5 g, 24.2 mmol) was dissolved in CH3CN (50 mL), cooled to 0°C and NCS (3.33 g, 25 mmol) was added in one portion. After the reaction was complete (concluded by HNMR) the organic solvent was evaporated to dryness and the crude mixture was partitioned between EtOAc (50 mL) and H2O (50mL).
• Step C To the pre-cooled to 0°C solution of N-(2-(2-amino-5- chlorothiazol-4-yl )ethyl)acetamide (3.7 g, 17.0 mmol) in CH 3 CN (50 mL) anhydrous CUCI2 (2.3g, 17 mmol) was added in one portion. After 10 min, tert-butyl nitrite (1.8g, 17.5 mmol) was added in a dropwise manner (reaction starts after addition of about 10% of the reagent; the start can be identified by the beginning of vigorous gas evolution) .
• Step A Ethyl 2-(2-aminothiazol-4-yl)-2,2-difluoroacetate (350 g, 1.58 mol) was dissolved in CH3CN (3 L), cooled to 0°C and NCS (215 g, 1.6 mol) was added in one portion. After the reaction was complete (concluded by HNMR) the organic solvent was evaporated to dryness and the crude mixture was partitioned between EtOAc (3 L) and H20 (1 L).
• Step B To the pre-cooled to 0°C solution of ethyl 2-(2-amino- 5-chlorothiazol-4-yl)-2,2-difluoroacetate (283 g, 1.1 mol) in CH3CN (3 L) anhydrous CuC12 (155 g, 1.15 mol) was added in one portion. After 10 min, tert-butyl nitrite (121 g, 1.16 mol) was added in a dropwise manner (reaction starts after addition of about 10% of the reagent; the start can be identified by the beginning of vigorous gas evolution).
• Step A To the pre-cooled to 0°C solution of ethyl 2—(2— aminothiazol-4-yl)-2,2-difluoroacetate (250 g, 1.12 mol) in CH3CN (3 L) anhydrous CuC12 (155 g, 1.15 mol) was added in one portion (Caution! Exothermic effect is observed! Heating up to 10°C). After 10 min, tert-butyl nitrite (121 g, 1.16 mol) was added in a dropwise manner (reaction starts after addition of about 10% of the reagent; the start can be identified by the beginning of vigorous gas evolution).
• Example 4 Effect of derivatives of heterocyclic amino acids on germination & early plants development.
• MEC Minimal Effective Concentration
• Example 6 Post-emergence herbicidal activity of selected derivatives of non-coded amino acids (DNAA).
• the tests were performed on Romaine lettuce (Lactuca sativa L.) plants at the stage 2 to 3 leaves. The plants were grown in mini-pots packed with soil, dimensions 2 X 2 X 5 cm, one plant per mini-pot. Test compounds were dissolved in 0.1% aqueous solution water solution of Silwet adjuvant to final concentrations ranging from 0 (Control) to 0.0001%. The test compounds were applied on soil (1 ml per pot) or foliar with airbrush (0.1 ml per pot). Each concentration was tested on 20 plants. Two weeks after the treatment the herbicidal effects of the respective test material were visually evaluated (aboveground part and roots. Then the aboveground part of the plants was neatly cut and weighed (wet weight) to assess the growth inhibition caused by the test compound. The growth inhibition (GI) was calculated as following:
• Mt and Me are median wet weight of treated and control plants, respectively.
• the herbicidal effect was assessed by concentration of the compound causing more than 85% of Growth Inhibition (GI)or irreversible damage of the plants (Table 3).
• Herbicidal activity of selected DHAAs is summarized in Table 4 (soil application) and Table 5 (Foliar application) . Table 3.
• the success criteria Scores of herbicidal activity
• Example 7 Herbicidal activity of selected DNAAs on the development of weeds.
• the herbicides were applied at dose from 0 (control) to 5 mg/pot. The treatment was performed at the day of sawn (pre-emergence treatment) . Then the pots were transferred to a mesh house 24 hours after herbicide application and were sprinkler irrigated to field capacity of the soil. Alternatively, the herbicides were applied on grown plants at stage 2 - 3 true leaves (post ⁇ emergence treatment).
• the plants were grown in the mesh house during the entire experiment. Plant development at 6, 12, 19, 26 and 32 days after application (DAA) were evaluated on a scale of 0 to 5, in which 0 represents dead plants and 5 represents healthy plants similar or not different from Control.
• DAA herbicidal effect was expressed as a score calculated as an average of assessments of plants vigor, height, and leaf color.
• FED Fully Effective Concentration
• Example 9 Comparison of herbicidal activity of selected derivatives of non-coded amino acids (DNAA) with structurally related non-coded amino acids
• test compounds were dissolved in 0.1% aqueous solution water solution of Silwet adjuvant.
• the test material where applied in rate 0 (Control),0.01, 0.05, and 0.5 mg/pot.
• the test compounds were applied on soil or foliar with airbrush (0.1 ml per pot). Each concentration was tested on 20 plants. Two weeks after the treatment the herbicidal effects of the respective test material were visually evaluated (aboveground part and roots. Then the aboveground part of the plants was neatly cut and weighed (wet weight) to assess the growth inhibition caused by the test compound.
• Mt and Me are median wet weight of treated and control plants, respectively.
• Compounds selected for the comparison of inhibitory effects are listed in the Table 8. Comparison of the herbicidal effects of non-coded amino acids (NAA) and their structural analogues, DNAA is summarized in the Table 9.
• aminoacyl-tRNA synthetases may acylate tRNA with selected non-coded amino acids thus facilitated inclusion of these molecules in nascent peptides. It was also suggested in the past that herbicidal activity of selected non- coded amino acids is based on its ability to acylate tRNA, be included in peptides and thus change 3D structure of cell proteins.
• a compound or “at least one compound” may include a plurality of compounds, including mixtures thereof .
• the compounds of the various formulas disclosed herein may contain chiral centers, e.g., asymmetric carbon atoms.
• the present disclosure is concerned with the synthesis of both: (i) racemic mixtures of the active compounds, and (ii) enantiomeric forms of the active compounds.
• the resolution of racemates into enantiomeric forms and racemization of optically active enantiomeric form can be done in accordance with known procedures in the art.
• Geometric isomers of double bonds and the like may also be present in the compounds disclosed herein, and all such stable isomers are included within the present disclosure unless otherwise specified.
• tautomers e.g., tautomers of triazole and/or imidazole
• rotamers All chains defined by the formulas herein which include three or more carbons may be saturated or unsaturated unless otherwise indicated. It is understood that substituents and substitution patterns on the compounds used in the method of the present invention can be selected by one of ordinary skill in the art to provide compounds that are chemically stable and that can be readily synthesized by techniques known in the art from readily available starting materials. If a substituent is itself substituted with more than one group, it is understood that these multiple groups may be on the same carbon or on different carbons, so long as a stable structure results.
• an “optionally substituted” group refers to a functional group in which one or more bonds to a hydrogen atom contained therein are replaced by a bond to non-hydrogen or non-carbon atoms, provided that normal valences are maintained and that the substitution results in a stable compound.
• Substituted groups also include groups in which one or more bonds to a carbon (s) or hydrogen (s) atom are replaced by one or more bonds, including double or triple bonds, to a heteroatom.
• the substituted compound can be independently substituted by one or more of the disclosed or claimed substituent moieties, singly or pluraly. By independently substituted, it is meant that the (two or more) substituents can be the same or different. In choosing the compounds of the present invention, one of ordinary skill in the art will recognize that the various substituents are to be chosen in conformity with well-known principles of chemical structure connectivity .
• H refers to a hydrogen atom.
• C refers to a carbon atom.
• N refers to a nitrogen atom.
• 0 refers to an oxygen atom.
• Halo refers to F, Cl, Br or I.
• hydroxy refers to an —OH moiety.
• Br refers to a bromine atom.
• Cl refers to a chlorine atom.
• I refers to an iodine atom.
• F refers to a fluorine atom.
• acyl group is intended to mean a group —C(0)—R, where R is a suitable substituent, for example, an acetyl group, a propionyl group, a butyroyl group, a benzoyl group, or an alkylbenzoyl group.
• R is a suitable substituent, for example, an acetyl group, a propionyl group, a butyroyl group, a benzoyl group, or an alkylbenzoyl group.
• Alkyl refers to a straight or branched chain hydrocarbon containing from 1 or 2 to 10 or 20 or more carbon atoms (e.g., C2, C3, C4, C5, C6, C7, C8, C9, CIO, Cll, C12, C13, C14, C15, etc.). In some embodiments the alkyl can be a lower alkyl.
• “Lower alkyl” refers to straight or branched chain alkyl having from 1 to 3, or from 1 to 5, or from 1 to 8 carbon atoms.
• Representative examples of alkyl include, but are not limited to, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert- butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, 3-methylhexyl, 2,2-dimethylpentyl, 2,3-dimethylpentyl, n-heptyl, n-octyl, n- nonyl, n-decyl, and the like.
• a carbon number range e.g., C1-C12 alkyl
• identification of a carbon number range is intended to include each of the component carbon number moieties within such range, so that each intervening carbon number and any other stated or intervening carbon number value in that stated range is encompassed, such that sub-ranges of carbon number within specified carbon number ranges may independently be specified.
• C1-C12 alkyl is intended to include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl and dodecyl, including straight chain as well as branched groups, as noted above, and the carbon number range ⁇ 31- C12 alkyl may also be more restrictively specified as sub-ranges such as C1-C4 alkyl, C2-C8 alkyl, C2-C4 alkyl, C3-C5 alkyl, or any other sub-range within the broader carbon number range.
• ranges of carbon numbers specifically excluding a carbon number or numbers are contemplated, as are sub-ranges excluding either or both of carbon number limits of specified ranges.
• “saturation” refers to the state in which all available valence bonds of an atom (e.g., carbon) are attached to other atoms.
• “unsaturation” refers to the state in which not all the available valence bonds are attached to other atoms; in such compounds the extra bonds usually take the form of double or triple bonds (usually with carbon).
• a carbon chain is “saturated” when there are no double or triple bonds present along the chain or directly connected to the chain (e.g., a carbonyl), and is “unsaturated” when at least one double or triple bond is present along the chain or directly connected to the chain (e.g., a carbonyl).
• a substituent depending upon chain saturation will be understood by those of ordinary skill in the art to depend upon the valence requirement of the atom or atoms to which the substituent binds (e.g., carbon).
• Alkenyl refers to a straight or branched chain hydrocarbon containing from 1 or 2 to 10 or 20 or more carbons, and containing at least one carbon-carbon double bond, formed structurally, for example, by the replacement of two hydrogens.
• alkenyl include, but are not limited to, ethenyl, 2-propenyl, 2-methyl-2-propenyl, 3-butenyl, 4-pentenyl, 5-hexenyl, 2- heptenyl, 2-methyl-l-heptenyl, 3-decenyl and the like.
• Alkynyl refers to a straight or branched chain hydrocarbon group containing from 1 or 2 to 10 or 20 or more carbon atoms, and containing at least one carbon-carbon triple bond.
• Representative examples of alkynyl include, but are not limited, to acetylenyl, 1-propynyl, 2-propynyl, 3-butynyl, 2-pentynyl, 1-butynyl and the like.
• cycloalkyl refers to a saturated cyclic hydrocarbon group containing from 3 to 8 carbons or more.
• heterocycle refers to a monocyclic, bicyclic or tricyclic ring system. Monocyclic heterocycle ring systems are exemplified by any 5 to 9-membered ring containing 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of: 0, N, and S.
• Aryl as used herein refers to a ring system having one or more aromatic rings.
• aryl include azulenyl, indanyl, indenyl, naphthyl, phenyl, tetrahydronaphthyl, and the like.
• Heteroaryl means a cyclic, aromatic hydrocarbon in which one or more carbon atoms have been replaced with heteroatoms (e.g., N, 0 or S). If the heteroaryl group contains more than one heteroatom, the heteroatoms may be the same or different.
• Alkoxy " as used herein, refers to an alkyl group, as defined herein, appended to the parent molecular moiety through an oxy group, as defined herein.
• An “amine” or “amino” is intended to mean the group —NH2.
• Primary amines have one of three hydrogen atoms replaced by an alkyl or aromatic group.
• Secondary amines have two organic substituents bound to the nitrogen together with one hydrogen.
• Tertiary amines have three organic substituents bound to the nitrogen.
• oxy refers to a —0— moiety.
• Niro refers to the organic compound functional group —N02.
• Agriculturally acceptable carriers include, without limitation, adjuvants, mixers, enhancers, etc. beneficial for application of the chemical formula. Suitable carriers should not be phytotoxic to valuable crops, particularly at the concentrations employed in applying the compositions for selective weed control in the presence of crops and should not react chemically with the compounds of the chemical formula herein or other composition ingredients. Such mixtures can be designed for application directly to weeds or their locus or can be concentrates or formulations which are normally diluted with additional carriers and adjuvants before application.
• They may include inert or active components and can be solids, such as, for example, dusts, granules, water dispersible granules, or wettable powders, or liquids, such as, for example, emulsifiable concentrates, solutions, emulsions or suspensions.
• Suitable agricultural carriers useful in preparing agricultural compositions of the present invention are well known to those skilled in the art.
• liquid carriers that can be employed include water, toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol monomethyl ether and diethylene glycol monomethyl ether, methanol, ethanol, isopropanol, amyl alcohol, ethylene glycol, propylene glycol, glycerine, and the like.
• Water is generally the carrier of choice for the dilution of concentrates.
• Suitable solid carriers include talc, pyrophyllite clay, silica, attapulgus clay, kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonire clay, Fuller's earth, cotton seed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, lignin, and the like.
• compositions of the present invention are advantageously employed in both solid and liquid compositions, especially those designed to be diluted with carrier before application.
• the surface-active agents can be anionic, cationic or nonionic in character and can be employed as emulsifying agents, wetting agents, suspending agents, or for other purposes.
• Typical surface active agents include salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol-C.sub.18 ethoxylate; alcohol- alkylene oxide addition products, such as tridecyl alcohol- C.sub.16 ethorylate; soaps, such as sodium stearate; alkylnaphthalenesulfonate salts, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryl trimethylammonium chloride; polyethylene glycol
• compositions can also contain other compatible components, for example, other herbicides, plant growth regulants, fungicides, insecticides, and the like and can be formulated with liquid fertilizers or solid, particulate fertilizer carriers such as ammonium nitrate, urea and the like.
• agriculturally acceptable salt is intended to mean a salt that retains the biological effectiveness of the free acids and bases of a specified compound and that is not biologically or otherwise undesirable.
• agriculturally acceptable salts include sulfates, pyrosulfates, bisulfates, sulfites, bisulfites, phosphates, monohydrogenphosphates , dihydrogenphosphates , metaphosphates, pyrophosphates, chlorides, bromides, iodides, acetates, propionates, decanoates, caprylates, acrylates, formates, isobutyrates, caproates, heptanoates, propiolates, oxalates, malonates, succinates, suberates, sebacates, fumarates, maleates, butyne- 1,4-dioates, hexyne-1,6-dioates, benzoates, chlorobenzoates , methylbenzoates, dinitrobenzoates, hydroxy
• range format is merely for convenience and brevity and should not be construed as an inflexible limitation on the scope of the invention. Accordingly, the description of a range should be considered to have specifically disclosed all the possible subranges as well as individual numerical values within that range. For example, description of a range such as from 1 to 6 should be considered to have specifically disclosed subranges such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6 etc., as well as individual numbers within that range, for example, 1, 2, 3, 4, 5, and 6. This applies regardless of the breadth of the range.
• method refers to manners, means, techniques and procedures for accomplishing a given task including, but not limited to, those manners, means, techniques and procedures either known to, or readily developed from known manners, means, techniques and procedures by practitioners of the chemical, agricultural, biological, and biochemical arts.
• plant growth regulator refers but not limited to a compound, either natural or synthetic, that modifies or controls one or more specific physiological processes within a plant.
• plant refers but not limited to whole plants, ancestors and progeny of the plants and plant parts, including seeds, shoots, stems, roots (including tubers), and plant cells, tissues and organs.
• the plant may be in any form including suspension cultures, embryos, meristematic regions, callus tissue, leaves, gametophytes, sporophytes, pollen, and microspores .
• crop protection agent refers but not limited to an agent which is a pesticide (or a mixture of more than one pesticide) or a plant growth regulator.
• pesticide refers to, but not limited to a chemical or biological agent that deters, incapacitates, kills, or otherwise discourages pests.
• compositions refers but not limited to a formulation, with at least one additional component selected from the oup consisting of surfactants, solid diluents and liquid diluents, which serves as a carrier.
• the formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredient, mode of application and environmental factors such as oil type, moisture and temperature.
• Useful compositions may include both liquid and solid formulation.
• Liquid formulations may include solutions (including emulsifiable concentrates), suspensions, emulsions (including icroemulsions, oil-in-water emulsions, flowable concentrates and/or suspoemulsions) and alike, which optionally can be thickened into gels.
• aqueous liquid compositions are soluble concentrate, suspension concentrate, capsule suspension, oncentrated emulsion, microemulsion, oil- in-water emulsion, flowable concentrate and uspo-emulsion.
• the general types of nonaqueous liquid compositions are emulsifiable oncentrate, microemulsifiable concentrate, dispersible concentrate and oil dispersion.
• solid formulations are dusts, powders, granules, pellets, prills, astilles, tablets, filled films (including seed coatings) and the like, which can be ater- dispersible ("wettable") or water-soluble. Films and coatings formed from film-forming solutions or flowable suspensions are particularly useful for seed treatment. Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively, the entire formulation of active ingredient can be encapsulated (or "overcoated”). Encapsulation can control or delay release of the active ingredient.
• Sprayable formulations are typically extended in a suitable medium before spraying.
• Such liquid and solid formulations are formulated to be readily diluted in the spray medium, usually water, but occasionally another suitable medium like an aromatic or paraffinic ydrocarbon or vegetable oil.
• Spray volumes can range from about one to several thousand liters per hectare, but more typically are in the range from about ten to several hundred liters per hectare.
• Sprayable formulations can be tank mixed with water or another suitable medium for foliar treatment by aerial or ground application, or for application to the growing medium of the plant.
• Liquid and dry formulations can be metered directly into drip irrigation systems or metered into the furrow during planting.
• the formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up to 100 percent by eight.
• the compounds of the invention have (both preemergent and postemergent) herbicidal activity.
• controlling undesired plant growth refers to killing or injuring the vegetation or reducing its growth.
• the compounds and compositions of the invention can be usefully applied by a variety of methods involving contacting a herbicidally effective amount of a compound of the invention, or a composition comprising said compound and at least one of a surfactant, a solid diluent or a liquid diluent, to the foliage or other part of the undesired plant or to the environment of the undesired plant growth such as the soil or water in which the undesired plant is growing or which surrounds the seed or other propagule of the undesired plant.
• a herbicidally effective amount of the compounds of this invention is determined by a number of factors: formulation selected, method of application, amount and type of undesired plant growth present, growing conditions, etc. In general, a herbicidally effective amount of compounds of this invention is about 0.001 to 20 kg/ha with a preferred range of about 0.004 to 1 kg/ha. One skilled in the art can easily determine the herbicidally effective amount necessary for the desired level of weed control.
• the compounds of the invention are applied, typically in a form of formulated composition, to a locus comprising desired vegetation (e.g., crops) and undesired plant growth (i.e. weeds), both of which may be seeds, seedlings and/or larger plants, in contact with a growth medium (e.g., soil).
• desired vegetation e.g., crops
• undesired plant growth i.e. weeds
• a composition comprising the compounds of the invention can be directly applied to a plant or any part of a plant thereof, particularly of the undesired plant growth, and/or to the growth medium in contact with the plant.
• Compounds of this invention can also be mixed with one or more other biologically active compounds or agents including herbicides, herbicide safeners, fungicides, insecticides, nematocides, bactericides, acaricides, plant growth regulators such as insect molting inhibitors and rooting stimulants, chemosterilants, semiochemicals , repellents, attractants, pheromones, feeding stimulants, plant nutrients, other biologically active compounds or bacteria, virus or fungi to form a multi-component pesticide giving broader spectrum of agricultural protection.
• Mixtures of the compounds of the invention with other herbicides can broaden the spectrum of activity against additional weed species and suppress the proliferation of any resistant biotypes.

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