WO1987004321A2 - Utilisation de composes heterocycliques contenant de l'azote pour reduire la perte d'humidite des plantes et augmenter le rendement des recoltes - Google Patents

Utilisation de composes heterocycliques contenant de l'azote pour reduire la perte d'humidite des plantes et augmenter le rendement des recoltes Download PDF

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WO1987004321A2
WO1987004321A2 PCT/US1987/000240 US8700240W WO8704321A2 WO 1987004321 A2 WO1987004321 A2 WO 1987004321A2 US 8700240 W US8700240 W US 8700240W WO 8704321 A2 WO8704321 A2 WO 8704321A2
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alkyl
substituted
unsubstituted
halogen
amino
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PCT/US1987/000240
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WO1987004321A3 (fr
Inventor
David Treadway Manning
James Joseph Cappy
Anson Richard Cooke
Richard Eric Sheads
Tai-Teh Wu
Anihal Lopes
Jennifer Lyn Phillips
Russell James Outcalt
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Rhone Poulenc Nederland BV
Union Carbide Agricultural Products Inc
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Rhone Poulenc Nederland BV
Union Carbide Agricultural Products Inc
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Priority to HU871236A priority Critical patent/HUT45848A/hu
Priority to FI874111A priority patent/FI874111A7/fi
Priority to BR8705356A priority patent/BR8705356A/pt
Publication of WO1987004321A2 publication Critical patent/WO1987004321A2/fr
Priority to KR870700857A priority patent/KR880700635A/ko
Priority to DK496187A priority patent/DK496187D0/da
Publication of WO1987004321A3 publication Critical patent/WO1987004321A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N3/00—Preservation of plants or parts thereof, e.g. inhibiting evaporation, improvement of the appearance of leaves or protection against physical influences such as UV radiation using chemical compositions; Grafting wax
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    • C07F9/65812—Cyclic phosphazenes [P=N-]n, n>=3
    • C07F9/65815—Cyclic phosphazenes [P=N-]n, n>=3 n = 3

Definitions

  • This invention relates to the use of heterocyclic nitrogen-containing compounds for reducing transpirational moisture loss from plants and also for increasing crop yield. This invention further relates to novel heterocyclic nitrogen-containing compounds and processes for the preparation thereof.
  • Transpiration is a well known physiolpgical process involving the passage of water in the form of a vapor through living tissues.
  • the water vapor passes through plant stomatal openings into the atmosphere, thus facilitating the absorption and translocation of aqueous nutrients by plant root systems.
  • the stomatal openings also permit necessary gaseous interchange between plant tissues and the external air. It is believed that only about one percent of the total water absorbed by plant roots is used for plant growth, the remainder being released through plant stomatal openings into the atmosphere by transpiration.
  • transpiration water loss from plants is important for several reasons; in particular, for decreasing requirements for irrigation water especially in dry climate regions, for protecting plants from wilting or other damage during transplantation or shipment or during severe cold weather, and for alleviating water stress in certain types of environments.
  • Water stress as used herein occurs when the transpiration rate exceeds the rate of water uptake by the plant. Water stress appears as a decrease in plant water potential and turgor and can result in wilting or other forms of damage or even plant death.
  • This invention relates to a method for reducing moisture loss from plants which comprises applying to the plant surface an effective amount, sufficient to reduce moisture loss from the plant surface without substantially inhibiting plant photosynthetic electron transport, of a compound having the formula:
  • R 1 , R 2 and X are as defined hereinafter.
  • This invention also relates to a method of increasing crop yield which comprises applying to the crop an effective amount, sufficient to increase crop yield without substantially inhibiting plant photosynthetic electron transport, of a compound having the formula:
  • R 1 , R 2 and X are as defined hereinafter.
  • This invention further relates to novel heterocyclic nitrogen-containing compounds and also to processes for the preparation of said compounds.
  • this invention relates to a method of reducing moisture loss from plants and increasing crop yields by the use of certain heterocyclic nitrogen-containing compounds. More particularly, this invention involves a method for reducing transpirational moisture loss from plants and increasing crop yield which comprises applying to the plant surface or crop an effective amount, sufficient to reduce moisture loss from the plant surface or to increase crop yield without substantially inhibiting plant photosynthetic electron transport, of a compound having the formula:
  • R 1 is a substituted or unsubstituted, carbocyclic or heterocyclic ring system selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, a polycyclic aromatic or nonaromatic ring system, and a bridged ring system which may be saturated or unsaturated in which the permissible substituents (Z) are the same or different and are one or more hydrogen, halogen, alkylcarbonyl, alkylcarbonylaIkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiocyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl,
  • R 1 is a substituted heteroatom or substituted carbon atom, or a substituted or unsubstituted, branched or straight chain containing two or more carbon atoms or heteroatoms in any combination in which the permissible substituents (Z) are the same or different and are one or more hydrogen, halogen, alkylcarbonyl, aIkylcarbonylaIkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiocyano, propargylthio, hydroxyimino, alkoxyimino, trialkyIsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, diaIky
  • X is a covalent single bond or double bond, a substituted or unsubstituted heteroatom or substituted carbon atom, or a substituted or unsubstituted, branched or straight chain containing two or more carbon atoms or heteroatoms in any combination in which the permissible substituents (Z) are the same or different and are one or more hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiocyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbony
  • R 2 is a substituted or unsubstituted, heterocyclic ring system having at least one nitrogen atom which is selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, a polycyclic aromatic or nonaromatic ring system, and a bridged ring system which may be saturated or unsaturated in which the permissible substituents (Z) are the same or different and are one or more hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiocyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulf
  • R 3 is a substituted or unsubstituted, carbocyclic or heterocyclic ring system selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, a polycyclic aromatic or nonaromatic ring system, and a bridged ring system which may be saturated or unsaturated in which the permissible substituents (Z) are the same or different and are one or more hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiocyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamid
  • -X - R 3 is a substituted heteroatom or substituted carbon atom, or a substituted or unsubstituted, branched or straight chain containing two or more carbon atoms or heteroatoms in any combination in which the permissible substituents (Z) are the same or different and are one or more hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiocyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylamino
  • Y 1 and Y 4 are independently oxygen or sulfur
  • Y 2 and Y 3 are independently oxygen. sulfur, amino or a covalent bond;
  • R 4 and R 5 are independently hydrogen or substituted or unsubstituted alkyl, polyhaloalkyl, phenyl or benzyl in which the permissible substituents (Z) are the same or different and are one or more hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiocyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, a1
  • alkenyl, haloalkenyl or polyhaloalkenyl alkylthio, polyhaloalkylthio, alkylsulfinyl, polyhaloalkylsulfinyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkylsulfonylamino, aIkylcarbonylamino, polyhaloalkylsulfonylamino, polyhaloalkylcarbonylamino, trialkylsilyl, aryldialkylsilyl, triarylsilyl, sulfonic acid and derivative salts, phosphonic acid and derivative salts, alkoxycarbonylamino, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, alkenyl, polyhaloalkenyl, alkenyloxy, alkynyl, alkynyloxy, polyhaloalkenyloxy, polyhaloalkynyl,
  • the alkyl-containing moieties above may contain from about 1 to about 100 carbon atoms or greater, preferably from about 1 to about 30 carbon atoms, and more preferably from about 1 to about 20 carbon atoms.
  • the polysaccharide moiety may contain up to about 50 carbon atoms. It is appreciated that all compounds encompassed within formula 1 are compounds having no unfilled bonding positions. It is further appreciated that in order for a substi-tuent to be permissible for the compounds encompassed within formula 1, the valence of the substituent must be appropriate with the bonding capability of the particular carbon atom or heteroatom.
  • B 1 represents a saturated or unsaturated carbon atom and A 1 represents a ring-forming chain of atoms which together with B 1 forms a cyclic system containing from 0 to 4 double bonds or from 0 to 2 triple bonds.
  • a 1 may contain entirely from 2 to 12 carbon atoms, may contain a combination of from 1 to 11 carbon atoms and from 1 to 4 heteroatoms which may be selected independently from N, O, S, P or other heteroatoms, or may contain 4 ring-forming heteroatoms alone.
  • Monocyclic ring systems encompassed by R 2 in formula 1 may include any monocyclic ring system of R 1 and R 3 having at least one nitrogen atom.
  • Ring-forming heteroatoms may in some cases bear oxygen atoms as in aromatic and aliphatic N-oxides and ring systems containing the sulfinyl, sulfonyl, selenoxide and phosphine oxide moieties.
  • Selected carbon atoms contained in cycles formed by B 1 and A 1 containing more than 3 ring-forming atoms may bear carbonyl, thiocarbonyl, substituted or unsubstituted imino groups or substituted or unsubstituted methylidene groups.
  • the group designated as Z represents one or more substituents selected independently from among the group of substituents defined for Z herein.
  • the cycle formed by B 1 and A 1 contains fewer than 4 ring forming members, it should be a saturated carbocycle, i.e. cyclopropyl.
  • the cycle formed by B and A contains fewer than 5 ring-forming members, it should contain no more than 1 heteroatom.
  • Bicyclic ring systems encompassed by R 1 and R 3 in formula 1 may be represented by generalized formulae 3 and 4 as follows:
  • B 2 and B 3 may be independently a saturated or unsaturated carbon atom or a saturated nitrogen atom
  • a 2 and A 3 independently represent the ring-forming chains of atoms described below and Z represents one or more substituents selected independently from among the group of substituents defined for Z herein.
  • Combinations of A 2 and A 3 may contain in combination with B 2 or B 3 from 0 to 5 double bonds.
  • a 2 and A 3 independent of B 2 and B 3 , may contain entirely from 1 to 11 carbon atoms, may contain a combination of 1 to 3 heteroatoms which may be selected independently from among N, O, S, P of other heteroatoms together with from 1 to 10 carbon atoms or may contain from 1-3 ring-forming heteroatoms alone.
  • Ring-forming heteroatoms may in some cases bear oxygen atoms, as in aromatic and aliphatic
  • N-oxides and ring systems containing the sulfinyl, sulfonyl, selenoxide and phosphine oxide groups are N-oxides and ring systems containing the sulfinyl, sulfonyl, selenoxide and phosphine oxide groups.
  • Selected carbon atoms contained in A 2 and A 3 may bear carbonyl, thiocarbonyl, substituted or unsubstituted imino groups or substituted or unsubstituted methylidene groups.
  • Bicyclic ring systems encompassed by R 2 in formula 1 may include any bicyclic ring system of R 1 and R 3 having at least one nitrogen atom.
  • bicyclic ring systems defined for R 1 and R 3 may be spirocyclic ring systems and are not limited to the fused bicyclic structures of formulae 3 and 4.
  • Spirocyclic ring systems may be saturated or unsaturated carbocyclic or- heterocyclic and may be independently substituted by one or more substituents Z as defined herein.
  • Polycyclic ring systems i.e., greater than 2 rings, encompassed by R 1 and R 3 in formula 1 may be represented by generalized formulae 5, 6, 7 and 8 as follows:
  • B 4 , B 5 , B 6 and B 7 may be independently a saturated or unsaturated carbon atom or a saturated nitrogen atom, and A 4 , A 5 , A 6 and A 7 independently represent ring forming chains of atoms which may contain together with one or the other (but not both) of their two associated bridgehead atoms, from 0-2 double bonds.
  • Z represent one or more substituents selected independently from among the group of substituents defined for Z herein.
  • the ring-forming elements of A 4 , A 5 , A 6 and A 7 independent of B 4 , B 5 , B 6 and B 7 may contain from 1-11 carbon atoms, may contain a combination of from 1-10 carbon atoms and from 1-3 heteroatoms which may be selected independently from among N, O, S, P or other heteroatoms, or may contain from 1-3 heteroatoms alone.
  • Ring-forming heteroatoms may in some cases bear oxygen atoms as in aromatic N-oxides and ring systems containing the sulfinyl, sulfonyl, selenoxide and phosphine oxide groups.
  • the group A 6 may at times be defined as a bond.
  • Selected carbon atoms contained in A 4 , A 5 , A 6 and A 7 may bear one or more carbonyl, thiocarbonyl or substituted or unsubstituted imino groups.
  • the groups B 8 , B 9 and B 10 represent independently a saturated or unsaturated carbon atom or a saturated nitrogen atom.
  • the group B 11 may represent a saturated or unsaturated carbon atom or a nitrogen or phosphorous atom.
  • the groups A 8 , A 9 and A 10 represent ring-forming chains of atoms which may contain together with 1 of the groups B 8 , B 9 , B 10 and B 11 from 0-2 double bonds.
  • the ring-forming elements of groups A 8 , A 9 and A 10 independent of groups B 8 , B 9 , B 10 and B 11 may contain from 2-10 carbon atoms, may contain from 1-10 carbon atoms in combination with 1-3 heteroatoms which may be selected independently from among N, O, S, P or other heteroatoms, or may contain from 2-3 heteroatoms alone. Ring-forming heteroatoms may in some cases bear oxygen atoms as in aromatic N-oxides and in ring systems containing the sulfinyl, sulfonyl, selenoxide and phosphine oxide groups. Selected carbon atoms contained in groups A 8 , A 9 and A 10 may bear one or more carbonyl, thiocarbonyl or substituted or unsubstituted imino groups.
  • polycyclic ring systems defined for R 1 and R 3 may be spirocyclic ring systems and are not limited to the fused polycyclic structures of formulae 5, 6, 7 and 8.
  • Spirocyclic ring systems may be saturated or unsaturated, carbocyclic or heterocyclic and may be independently substituted by one or more substituents Z as defined herein.
  • Polycyclic ring systems encompassed by R 2 of formula 1 may include any polycyclic ring system or R 1 and R 3 having at least one nitrogen atom.
  • Illustrative polycyclic ring structures which are encompassed by R 1 and R 3 in formula 1 include the following:
  • Bridged bicyclic structures encompassed by R 1 and R 3 in formula 1 may be represented by generalized formulae 9, 10, and 11 as follows:
  • B 12 and B 13 may be independently a saturated carbon atom optionally substituted by Z or a nitrogen atom, and the groups A 11 , A 12 and A 13 independently represent ring-forming chains of atoms which may contain, independently of B 12 and B 13 , from 0-2 double bonds.
  • the groups Z represent one or more substituents selected independently from among the groups of substituents defined for Z herein.
  • the ring-forming elements of A 11 , A 12 and A 13 may contain entirely from 1-11 carbon atoms, may contain a combination of from 1-10 carbon atoms and from 1-3 heteroatoms which may be selected independently from among N, O, S, P or other heteroatoms, or may contain from 1-3 heteroatoms alone with the proviso that when one of the groups A 11 , A 12 and A 13 is a single heteroatom, the other two groups should contain two or more ring-forming atoms.
  • a second proviso is that when one or both of the groups B 12 and B 13 is nitrogen, the groups A 11 , A 12 and A 13 should contain at least two saturated ring-forming atoms.
  • Ring-forming heteroatoms may in some cases bear oxygen atoms as in the sulfinyl, sulfonyl, selenoxide and phosphine oxide moieties.
  • Selected carbon atoms contained in A 11 , A 12 and A 13 may bear one or more carbonyl, thiocarbonyl or substituted or unsubstituted imino groups.
  • Bridged bicyclic structures encompassed by R 2 of formula 1 may include any bicyclic bridged system of R 1 and R 3 having at least one nitrogen atom.
  • the substituent X may be an unsubstituted heteroatom such as an oxygen or sulfur, as in carbonyl and thiocarbonyl systems, or may be a substituted heteroatom or carbon atom.
  • X may also be a covalent single or double bond.
  • X may further be a saturated or unsaturated, branched or straight chain of carbon atoms; a branched or straight, saturated or unsaturated chain of atoms consisting of both carbon atoms and heteroatoms; or may be a branched or straight, saturated or unsaturated chain consisting entirely of heteroatoms.
  • Selected heteroatomic components of X may bear oxygen atoms as in the case of groups containing the sulfonyl, sulfinyl, N-oxide and phosphine oxide moieties.
  • Selected heteroatomic components of X may bear one or more substituents Z as defined herein.
  • Selected carbon atoms participating in X may bear carbonyl, thiocarbonyl, substituted or unsubstituted imino, substituted or unsubstituted alkylidene or one or more substituents Z as defined herein.
  • R 10 and R 11 are independently hydrogen or substituted or unsubstituted alkyl, polyhaloalkyl, phenyl or benzyl in which the permissible substituents are as defined for Z herein.
  • formula 1 encompasses a wide variety of heterocyclic nitrogen-containing compounds.
  • Illustrative heterocyclic nitrogen-containing compounds within the scope of formula 1 which may be used for reducing transpirational moisture loss from plants and increasing crop yield are included in Tables 1 through 43 below.
  • novel heterocyclic nitrogen-containing compounds of this invention can be depicted by the following formulae:
  • R 24 represents unsubstituted or substituted phenyl, 1- or 2-naphthyl or heteroaryl; x 10 represents O, S, SO, SO 2 , NH,
  • Y 19 is the same or different and represents halogen, alkyl, cyano, polyhaloalkyl, alkoxy, polyhaloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, acyl or polyhaloalkylsulfonyl; provided that (i) at least two ring position pairs selected from 2 and 4, 2 and 6, 2 and 3, and 3 and 4 are substituted with the same or different halogen; (ii) when ring positions 2,4 and 6 are substituted with chlorine and j is a value of 0 and X 10 is
  • R 24 is not unsubstituted phenyl
  • R 25 represents unsubstituted or substituted phenyl, 1- or 2-naphthyl or heteroaryl
  • X 11 represents O, S, SO, SO 2 , NH,
  • b is a value of 2 to 3;
  • Y 20 is the same or different and represents halogen, alkyl, cyano, polyhaloalkyl, polyhaloalkoxy, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, acyl or polyhaloalkylsulfonyl provided that at least two ring position pairs selected from 2 of Y 20 are halogen;
  • R 26 represents unsubstituted or substituted phenyl, 1- or 2-naphthyl or heteroaryl
  • X 12 represents O, S, SO, SO , NH,
  • Y 21 and Y 22 are independently the same or different halogen
  • Y 23 represents hydrogen, halogen, alkyl, polyhaloalkyl, alkoxy, polyhaloalkoxy, cyano, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, acyl or polyhaloalkylsulfonyl;
  • R 27 represents unsubstituted or substituted phenyl, 1- or 2-naphthyl or heteroaryl
  • X represents O, S, SO, SO 2 , NH,
  • Y 24 represents halogen
  • Y 25 and Y 26 independently represent hydrogen, halogen, alkyl, polyhaloalkyl, alkoxy, polyhaloalkoxy, cyano, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, acyl or polyhaloalkylsulfonyl provided that at least one of Y 25 and Y 26 is halogen and further provided that when Y 24 , Y 25 and Y 26 are chloro and X 13 is O, then R 27 is not unsubstituted phenyl;
  • R 28 represents unsubstituted or substituted phenyl, 1- or 2-naphthyl or heteroaryl
  • X 14 represents O, S, SO, SO 2 , NH,
  • Y 27 and Y 28 are independently halogen
  • Y 29 represents hydrogen, halogen, alkyl, polyhaloalkyl, alkoxy, polyhaloalkoxy, cyano, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, acyl or polyhaloalkylsulfonyl;
  • R 29 represents unsubstituted or substituted phenyl, 1- or 2-naphthyl or heteroaryl
  • X 15 represents O, S, SO, SO 2 , NH,
  • Y 30, Y 31 and Y 32 independently represent hydrogen, halogen, alkyl, cyano, polyhaloalkyl, alkoxy, polyhaloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro. acyl or polyhaloalkylsulfonyl provided that at least 2 of
  • Y 30 , Y 31 and Y 32 are halogen
  • R 30 represents unsubstituted or substituted phenyl, 1- or 2-naphthyl or heteroaryl
  • X 16 represents O, S, SO, SO 2 , NH,
  • Y 33 , Y 34 and Y 35 independently represent hydrogen, halogen, alkyl, cyano, polyhaloalkyl, alkoxy, polyhaloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, acyl or polyhaloalkylsulfonyl provided that (i) at least 2 of Y 33 , Y 34 and Y 35 are halogen, (ii) when Y 34 and Y 35 are both chloro and X 16 is O, then
  • R 30 is not unsubstituted phenyl, and (iii) when Y 33 and Y 34 are both chloro and X 16 is O, the
  • R 30 is not unsubstituted phenyl or 4-methoxyphenyl
  • d is a value of from 0 to 4 inclusive
  • e is a value of 1 or 2 provided that d and e are not greater than 5;
  • R 31 is the same or different and represents unsubstituted or substituted aryl provided that when R 31 is 2- or 4-aryl then d is not O, aralkyl provided that when R 31 is R-aralkyl then d is not O, alkoxy.
  • cycloalkoxy, aryloxy, aralkoxy provided that when R 31 is 4-aralkoxy then d is not O, arylaryloxy, aralkoxyaralkyl, arylaralkoxy.aryloxyaralkyl, aryloxyalkyl, aryloxyaryloxy, aralkoxyaralkoxy, aryloxyalkoxy, alkylthio, alkenylthio, arylthio, aralkylthio, arylthioaralkyl, arylsulfonylarylsulfonyl, alkylamino, dialkylamino, acyloxy, aroyloxy, alkoxycarbonyloxy, phenylazo provided that X 17 is O or S, naphthylazo, or -OCH 2 O- or -OCH 2 CH 2 O which join adjacent carbon atoms to form a five- or six-membered ring;
  • X 17 represents O, S, NH, CH 2 , -CH 2 O-, -CH 2 S- or -OCH 2 CH 2 O-;
  • Y 37 represents halogen
  • Y 38 represents halogen, alkoxy. alkylthio, alkylsulfonyl, polyhaloalkoxy, polyhaloalkyl, cyano, nitro or unsubstituted or substituted arylthio, aryloxy or arylsulfonyl;
  • f is a value of from 0 to 5;
  • R 32 is the same or different and represents halogen, alkyl, alkenyl, alkynyl, polyhaloalkyl, cyano, nitro, alkylamino, dialkylamino, alkoxy, polyhaloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, polyhaloalkylsulfonyl, acyl, CO 2 (alkyl), CONH(alkyl), CON(alkyl) 2 , SO 2 N(alkyl) 2 , alkylcarbonyloxy, alfcoxycarbonyloxy, or unsubstituted or substituted aryloxy, arylthio, arylsulfonyl or aroyl;
  • X 18 represents O, S, CH 2 , a single covalent bond or -C ⁇ C-;
  • Y 39 represents halogen, polyhaloalkoxy, polyhaloalkyl. cyano, alkylsulfonyl, alkylsulfonyloxy, polyhaloalkylsulfonyl or polyhaloalkylsulfonyloxy; and Y 40 represents haloalkyl, polyhaloalkyl, alkoxy provided that X 18 is not S or a single covalent bond; polyhaloalkoxy, cyano, alkylthio provided that X 18 is not 0 or a single covalent bond; alkylsulfonyl, nitro, dialkoxyphosphinyl or trialkylammonium;
  • Y 41 is the same or different and represents halogen
  • Y 42 is the same or different and represents halogen, alkoxy, alkylthio or polyhaloalkoxy:
  • Y 52 and Y 53 are independently halogen; g is a value of from 0 to 5 inclusive;
  • X 20 represents -CH(alkyl)O-, -C(alkyl) 2 O-, -OCH 2 -, -CH 2 O-, -CH 2 -, -C(halogen) 2 , -OCH 2 O-, -OCH 2 CH 2 O- or -C ⁇ C- provided that g is a value of at least 1;
  • R 34 represents acyl, alkylsulfonyl, polyhaloalkyl, polyhaloacyl, polyhaloalkylsulfonyl or unsubstituted or substituted aroyl or arylsulfonyl and Y 43 and
  • Y 44 are independently O or S
  • R 35 represents an unsubstituted or substituted heterocyclic ring system selected from isoxazole, isothiazole, pyrazole, imidazole, 1,2,4-triazole, 1,2,4-oxadiazole, 1,3,4-oxadiazole, 1,2,4,-thiadiazole, 1,3,4-thiadiazole, oxazole, thiazole, benzopyrazole, benzimidazole, benzoxazole, benzothizole, indole, pyrrole, furan, thiophene, benzofuran, benzothiophene, pyridine, pyrimidine, pyridazine, pyrazine, 1,3,5-triazine, 1,2,4-triazine, quinoline, isoquinoline, quinazoline, phthalazine, benzopyridazine, benzopyrazine, carbazole, dibenzofuran, dibenzothiophene, benzox
  • X 21 represents O, S or NH provided that when X 21 is NH then R 35 is not pyridine, and when X 21 is S then R 35 is not unsubstituted benzothiazole;
  • Y 45 and Y 46 are independently halogen
  • R 37 and R 38 independently represent halogen, nitro, cyano, polyhaloalkyl, polyhaloalkoxy, alkylsulfonyl, polyhaloalkylsulfonyl, acyl, alkoxycarbonyl, polyhaloalkylsulfonyl or R 39 -X 22 - Provided that only one of R 37 and R 38 may be R 39 -X 22 - at any one time;
  • R 39 represents unsubstituted or substituted phenyl, 1- or 2-naphthyl or heteroaryl
  • X 22 represents O, S, SO, SO 2 , CH 2 , a single covalent bond, -CH 2 O-, -CH 2 S-,
  • Y 47 represents halogen
  • B 14 represents O, S, NH or N R 40 wherein
  • R 40 represents alkyl, alkylsulfonyl, alkenyl, alkynyl, alkoxycarbonyl; unsubstituted or substituted aryl, aralkyl, aryloxy, arylamino, aroyl or arylsulfonyl; provided that (i) when B 14 is
  • R 39 - , R 39 -alkyl- R 39 -C( O)- ,
  • R 37 and R 38 are other than R 39 - X 22 -; (ii) when B 14 is other than R 39 - , R 39 -alkyl- ,
  • R 41 and R 42 independently represent halogen or R 43 - X 23 - provided that only one of
  • R 41 and R 42 may be R 43 - X 23 - at any one time;
  • R 43 represents unsubstituted or substituted phenyl, 1- or 2-naphthyl or heteroaryl
  • X 23 represents O, S, SO, SO 2 , CH 2 , a single covalent bond, -CH 2 O-, CH 2 S-,
  • B 15 represents O, S, NH or N R 44 wherein
  • R 44 represents alkyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkenyl, alkynyl, alkoxycarbonyl; unsubstituted or substituted aryl, aralkyl, aryloxy, arylamino, aroyl or arylsulfonyl; provided that when R 15 is
  • R 41 and R 42 are other than R 43 -X 23 -; and further provided that when B 15 is other than
  • R 45 , R 46 , R 47 , and R 48 independently represent hydrogen, halogen, nitro, cyano, polyhaloalkyl, polyhaloalkoxy, alkylsulfonyl, polyhaloalkylsulfonyl, acyl, alkylthio, alkyl, alkoxy, alkylsulfinyl or R 49 -X 24 - provided that one of R 45 , R 46 , R 47 , and R 48 is
  • R 47 and R 48 include no more than two of hydrogen, alkyl or alkoxy at any one time;
  • R 49 represents unsubstituted or substituted phenyl, 1- or 2-naphthyl or heteroaryl;
  • X represents O, S, SO, SO 2 , CH 2 , a single covalent bond, -CH 2 O-, -CH 2 S-,
  • Y 48 represents halogen
  • B 16 represents O, S or NH
  • R 50 represents an unsubstituted or substituted, carbocyclic or heterocyclic ring system selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, a polycyclic aromatic or nonaromatic ring system, and a bridged ring system which may be saturated or unsaturated;
  • Y 54 and Y 55 are independently halogen
  • R 51 represents or unsubstituted or substituted, carbocyclic or heterocyclic ring system selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, a polycyclic aromatic or nonaromatic ring system, and a bridged ring system which may be saturated or unsaturated;
  • B 19 represents -CH 2 - or -CH(alkyl)-; and i is a value of 0 or 1;
  • Y 56 and Y 57 are independently halogen
  • B 20 represents -CH 2 C(CH 3 ) 4 SCH 2 -
  • -CH 2 CH C(CH 3 )OCH 2 -, -CH 2 CH 2 SCH 2 CH(CH 3 )-,
  • R 52 represents hydrogen, alkenyl; unsubstituted or substituted aryl or alkaryl;
  • Y 58 and Y 59 are independently halogen
  • X 25 represents O, S, NH, CH 2 -CH 2 O- or a single covalent bond
  • R 54 is the same or different and is one or more hydrogen, halogen, alkyl, aryl, aralkyl, alkenyl, alkynyl, polyhaloalkyl, NH 2 , NH(alkyl),
  • N(alkyl) 2 alkoxy, polyhaloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, aralkoxy, CO 2 alkyl,
  • X 26 represents O, S, SO, SO 2 , CH 2 , a single covalent bond, -CH 2 O-, -CH 2 S-,
  • Y 50 and Y 51 are the same or different and are halogen
  • R 68 represents unsubstituted or substituted phenyl or 1- or 2-naphthyl
  • X 27 represents -CH(alkyl)O-, -C(alkyl) 2 O-, -OCH 2 -, -C(halogen) 2 , -OCH 2 O-, -OCH 2 CH 2 O-, -CH 2 O-, -C ⁇ C-, -OCH(alkyl)-,
  • R 34 represents acyl, alkylsulfonyl, polyhaloalkyl, polyhaloacyl, polyhaloalkylsulfonyl or unsubstituted or substituted aroyl or arylsulfonyl and Y 43 and
  • Y 44 are independently O or S
  • Z 1 and Z 2 are independently O, S, C 1 -C 8 alkylidene, substituted or unsubstituted benzylidene, NH or NR''' wherein R''' is alkyl, aryl, aralkyl, alkenyl or alkynyl: and
  • Y 67 and Y 68 are the same or different and represent hydrogen,halogen, alkyl, cyano, polyhaloalkyl, alkoxy, polyhaloalkoxy, haloalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, aryl, polyhaloalkylsulfonyl, alkylamino, dialkylamino, acylamino, acyloxy, alkylsulfonyloxy, arylsulfonyloxy, alkenylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, phosphono or phosphino;
  • R 69 represents unsubstituted or substituted phenyl or 1- or 2-naphthyl
  • X 28 is NH, CH 2 or a covalent bond
  • Z 3 and Z 4 are independently O, S, C 1 -C 8 alkylidene, substituted or unsubstituted benzylidene, NH or NR''' wherein R''' is alkyl, aryl, aralkyl, alkenyl or alkynyl; and
  • Y 69 and Y 70 are the same or different and represent hydrogen, halogen, alkyl, cyano, polyhaloalkyl, alkoxy, polyhaloalkoxy, haloalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, aryl, polyhaloalkylsulfonyl, alkylamino, dialkylammo, acylamino, acyloxy, alkylsulfonyloxy, arylsulfonyloxy, alkenylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, phosphono or phosphino, with the proviso that Y 69 and Y 70 taken together do not represtt eeiitthheerr the same halogen or halogen and hydrogen;
  • R 70 represents an unsubstituted or substituted, unsaturated or saturated, aromatic or non-aromatic heterocyclic ring system selected from isoxazole, isothiazole, pyrazole, imidazole, 1,2,4-triazole, 1,2,4-oxadiazole, 1,3,4-oxadiazole, 1,2,4,-thiadiazole, 1,3,4-thiadiazole, oxazole, thiazole, benzopyrazole, benzimidazole, benzoxazole, benzothizole, indole, pyrrole, furan, thiophene, benzofuran, benzothiophene, pyridine, pyrimidine, pyridazine, pyrazine, 1,3,5-triazine, 1,2,4-triazine, quinoline, isoquinoline, quinazoline, phthalazine, benzopyridazine, benzopyrazine, carbazole, dibenzo
  • X 29 represents -CH(alkyl)O-, -C(alkyl) 2 O-, -OCH 2 -, -CH 2 O-, -CH 2 -, a covalent bond, -C(halogen) 2 , -OCH 2 O-,
  • R 34 represents acyl, alkylsulfonyl, polyhaloalkyl, polyhaloacyl, polyhaloalkylsulfonyl or unsubstituted or substituted aroyl or arylsulfonyl and Y 43 and
  • Y 44 are independently O or S;
  • Z 5 and Z 6 are independently O, S, C 1 -C 8 alkylidene, substituted or unsubstituted benzylidene, NH or NR''' wherein R''' is alkyl , aryl, aralkyl , alkenyl or alkynyl ; and
  • Y 71 and Y 72 are the same or different and represent hydrogen, halogen, alkyl, cyano, polyhaloalkyl, alkoxy, polyhaloalkoxy, haloalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, acyl, polyhaloalkylsulfonyl, amino, alkylamino, dialkylamino, acylamino, acyloxy, alkylsulfonyloxy, arylsulfonyloxy, alkenylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, alkoxycarbonyl, alkylaminocarbonyl, aminocarbonyl, dialkylaminocarbonyl, dialkylaminosulfonyl, alkylaminosulfonyl, .aminosulfonyl, dialkoxyalky
  • R 71 represents unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkadienyl, cycloalkatrienyl, bicycloalkyl, bicycloalkenyl, bicycloalkadienyl, tricycloalkyl, tricycloalkenyl or tricycloalkadienyl:
  • X 30 represents -CH(alkyl)O-, -C(alkyl) 2 O-, -OCH 2 -, -CH 2 O-, -CH 2 -, a covalent bond, -C(halogen) 2 , -OCH 2 O-, -OCH 2 CH 2 O-, -C ⁇ C-, -OCH(alkyl)-, -OC(alkyl) 2 , -OCH(alkyl)O-, -OC(alkyl) 2 O-, -OCH(alkyl)CH 2 O-, -OCH(alkyl)CH(alkyl)O-, -CH(alkyl)CH(alkyl)-, -CH(alkyl)-, -C(alkyl) 2 -, -CH 2 CH 2 O-, -OCH 2 CH 2 -, -CH(alkyl)CH 2 O-, -CH 2 CH 2 -, -CH(CN)O
  • R 34 represents acyl, alkylsulfonyl, polyhaloalkyl, polyhaloacyl, polyhaloalkylsulfonyl or unsubstituted or substituted aroyl or arylsulfonyl and Y 43 and
  • Y 44 are independently O or S;
  • Z 7 and Z 8 are independently O, S, C 1 -C 8 alkylidene, substituted or unsubstituted benzylidene, NH or NR''' wherein R''' is alkyl, aryl, aralkyl, alkenyl or alkynyl; and
  • Y 73 and Y 74 are the same or different and represent hydrogen,halogen, alkyl, cyano, polyhaloalkyl, alkoxy, polyhaloalkoxy, haloalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, aryl, polyhaloalkylsulfonyl, alkylamino, dialkylamino, acylamino, acyloxy, alkylsulfonyloxy, arylsulfonyloxy, alkenylsulfonyloxy, haloalkylsulfonyloxy and polyhaloalkylsulfonyloxy;
  • B 21 represents -CH 2 C(CH 3 ) 2 SCH 2 -
  • R 52 represents hydrogen, alkenyl; unsubstituted or substituted aryl or alkaryl; Z 9 and Z 10 are independently O, S, C 1 -C 8 alkylidene, substituted or unsubstituted benzylidene, NH or NR''' wherein R''' is alkyl, aryl, aralkyl, alkenyl or alkynyl; and
  • Y 75 and Y 76 are the same or different and represent hydrogen,halogen, alkyl, cyano, polyhaloalkyl, alkoxy, polyhaloalkoxy, haloalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, acyl, polyhaloalkylsulfonyl, amino, alkylamino, dialkylamino, acylamino, acyloxy, alkylsulfonyloxy, arylsulfonyloxy, alkenylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, phosphono or phosphino;
  • R 72 represents unsubstituted or substituted phenyl or 1- or 2-naphthyl
  • X 31 represents -OCH 2 -, -CH 2 -, a covalent bond, -C(halogen) 2 , -C ⁇ C-, -OCH(alkyl)-,
  • h is a value of from 0 to 2 inclusive
  • Z 11 represents O, S, C 1 -C 8 alkylidene, substituted or unsubstituted benzylidene, NH or NR''' wherein R''' is alkyl, aryl, aralkyl, alkenyl or alkynyl; and
  • Y 77 , Y 78 and Y 79 are the same or different and represent hydrogen,halogen, alkyl, hydroxy, cyano, polyhaloalkyl, alkoxy, polyhaloalkoxy, haloalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, acyl, polyhaloalkylsulfonyl, aIkylamino, amino, dialkylamino, acylamino, acyloxy, alkylsulfonyloxy, arylsulfonyloxy, alkenylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, phosphono or phosphino, with the proviso that when Y 77 is halogen and
  • Y 79 is hydrogen then Y 78 cannot be amino, alkylamino, dialkylamino or acylamino and with the further proviso that when Y 77 and Y 78 are the same halogen then Y 79 cannot be hydrogen or hydroxy;
  • R 73 represents an unsubstituted or substituted, unsaturated or saturated, aromatic or non-aromatic heterocyclic ring system selected from isoxazole, isothiazole, pyrazole, imidazole, 1,2,4-triazole, 1,2,4-oxadiazole, 1,3,4-oxadiazole, 1,2,4,-thiadiazole, 1,3,4-thiadiazole, oxazole, thiazole, benzopyrazole, benzimidazole, benzoxazole, benzothizole, indole, pyrrole, furan, thiophene, benzofuran, benzothiophene, pyridine, pyrimidine, pyridazine, pyrazine, 1,3,5-triazine, 1,2,4-triazine, quinoline, isoquinoline, quinazo ⁇ ine, phthalazine, benzopyridazine, benzopyrazine, carbazole, di
  • X 32 represents -OCH 2 -, -CH 2 -, a covalent bond, -C(halogen) 2 , -C ⁇ C-, -OCH(alkyl)-, -OC(alkyl) 4 , -CH(alkyl)CH(alkyl)-, -CH(alkyl)-,
  • h is a value of from 0 to 2 inclusive
  • Z 12 represents O, S, C 1 -C 8 alkylidene, substituted or unsubstituted benzylidene, NH or NR''' wherein R''' is alkyl, aryl, aralkyl, alkenyl or alkynyl; and
  • Y 80 , Y 81 and Y 82 are the same or different and represent hydrogen,halogen, alkyl, hydroxy, cyano, polyhaloalkyl, alkoxy, polyhaloalkoxy, haloalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, acyl, polyhaloalkylsulfonyl, alkylamino, amino, dialkylamino, acylamino, acyloxy, alkylsulfonyloxy, arylsulfonyloxy, alkenylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, phosphono or phosphino;
  • R 74 represents unsubstituted or substituted alkyl, alkenyl, alkynyl, cyploalkyl cycloalkenyl, cycloalkadienyl, cycloalkatrienyl, bicycloalkyl, bicycloalkenyl, bicycloalkadienyl, tricycloalkyl, tricycloalkenyl or tricycloalkadienyl;
  • X 33 represents -OCH 2 -, -CH 2 -, a covalent bond, -C(halogen) 2 , -C ⁇ C-, -OCH(alkyl)-, -OC(alkyl) 2 , -CH(alkyl)CH(alkyl)-, -CH(alkyl)-,
  • h is a value of from 0 to 2 inclusive
  • Z 13 represents O, S, H 2 -H 2 alkylidene, substituted or unsubstituted benzylidene, NH or NR''' wherein R''' is alkyl, aryl, aralkyl, alkenyl or alkynyl: and Y 83 , Y 84 and Y 85 are the same or different and represent hydrogen, halogen, alkyl, hydroxy, cyano, polyhaloalkyl, alkoxy, polyhaloalkoxy, haloalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, acyl, polyhaloalkylsulfonyl, alkylamino, amino, dialkylammo, acylamino, acyloxy, alkylsulfonyloxy, arylsulfonyloxy, alkenylsulfonyloxy, haloalkylsulfon
  • Y 62 , Y 63 , Y 64 , Y 65 and Y 66 are the same or different and are halogen;
  • R 1 is a substituted or unsubstituted, carbocyclic or heterocyclic ring system selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, a polycyclic aromatic or nonaromatic ring system, and a bridged ring system which may be saturated or unsaturated in which the permissible substituents are the same or different and are one or more hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiocyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formaraidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhalo
  • R 1 is a substituted heteroatom or substituted carbon atom, or a substituted or unsubstituted, branched or straight chain containing two or more carbon atoms or heteroatoms in any combination in which the permissible substituents are the same or different and are one or more hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiocyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylammocarbonyl, diaIkylaminocarbony
  • X is a covalent single bond or double bond, a substituted or unsubstituted heteroatom or substituted carbon atom, or a substituted or unsubstituted, branched or straight chain containing two or more carbon atoms or heteroatoms in any combination in which the permissible substituents are the same or different and are one or more hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiocyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, al
  • R 36 is a substituted or unsubstituted, asymmetrical heterocyclic ring system having at least three nitrogen atoms which are selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, a polycyclic aromatic or nonaromatic ring system, and a bridged ring system which may be saturated or unsaturated in which the permissible substituents are the same or different and are one or more hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiocyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxys
  • R 3 is a substituted or unsubstituted, carbocyclic or heterocyclic ring system selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, a polycyclic aromatic or nonaromatic ring system, and a bridged ring system which may be saturated or unsaturated in which the permissible substituents are the same or different and are one or more hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiocyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhalo
  • R 3 is a substituted heteroatom or substituted carbon atom, or a substituted or unsubstituted, branched or straight chain containing two or more carbon atoms or heteroatoms in any combination in which the permissible substituents are the same or different and are one or more hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiocyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl,
  • Y 1 and Y 4 are independently oxygen or sulfur
  • Y 2 and Y 3 are independently oxygen, sulfur, amino or a covalent bond
  • R 4 and R 5 are independently hydrogen or substituted or unsubstituted alkyl, polyhaloalkyl, phenyl or benzyl in which the permissible substituents are the same or different and are one or moris hydrogen, halogen, alkylcarbonyl , alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiocyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylamin
  • the heterocyclic nitrogen-containing compounds encompassed within formula 1 can be prepared by conventional methods known in the art, and many may be available from various suppliers.
  • the novel heterocyclic nitrogen-containing compounds of formulae (i) through (xxxiii) above which may be used in the method of this invention can be prepared by reacting appropriate starting ingredients in accordance with conventional procedures described in the art as illustrated below.
  • novel heterocyclic nitrogen-containing compounds of formula (i) can be prepared by the following general reaction scheme:
  • R 24 , X 10 , a, j and Y 19 are as defined hereinabove.
  • Reactions of this general type for preparing substituted pyridines including process conditions are described for example by Mertel, H.E., The Chemistry of Heterocyclic Compounds, Pyridine and Derivatives-Part Two, Halopyridines, P. 351, Interscience, Wiley, New York (1961). Intermediates such as 2,4,6-trichloropyridine are described in U.S. Patent 3.830,820.
  • other preparation methods for the novel compounds of formula (i) are described in Fuson. R.C., Advanced Organic Chemistry, p. 124, Wiley, New York (1950), and Ochiai, E., Aromatic Amine Oxides, p. 21, Elsevier, New York (1967).
  • novel heterocyclic nitrogen-containing compounds of formula (ii) can be prepared by the following general reaction scheme:
  • R 25 , X 11 , b and Y 20 are as defined hereinabove. Reactions of this general type for preparing substituted pyrazines including process conditions are described for example in U.S. Patent 4.254,125.
  • novel heterocyclic nitrogen-containing compounds of formula (iii) can be prepared by the following general reaction scheme:
  • novel heterocyclic nitrogen-containing compounds of formula (v) can be prepared by the following general reaction scheme:
  • R 28 , X 14 , Y 27 , Y 28 and Y 29 are as defined hereinabove.
  • Reactions of this general type for preparing 5-substituted pyrimidines including process conditions and intermediate preparations are described for example by Fieser, L.F. and Fieser, M., Organic Chemistry, p. 310, Heath, Boston (1972) also Brown, D.J., The Pyrimidines; The Chemistry of Heterocyclic Compounds, pp. 50, 166, Interscience, Wiley, New York (1962).
  • the novel heterocyclic .nitrogen-containing compounds of formula (vi) can be prepared by the following general reaction scheme:
  • novel heterocyclic nitrogen-containing compounds of formula (vii) can be prepared by the following general reaction scheme:
  • novel heterocyclic nitrogen-containing compounds of formula (viii) can be prepared by the following general reaction scheme:
  • 1,3,5-triazines including process conditions and intermediate preparations are described for example in German Patent 952,478, U.S. Patent 2,824,823.
  • R 32 , f, X 18 , Y 39 , Y 40 and Y 49 are as defined hereinabove.
  • Reactions of this general type for preparing substituted 1,3,5-triazines including process conditions and intermediate preparations are described for example in U.S. Patent 3,316,264.
  • Intermediates such as 2,4-dichloro-6-(diethoxyphosphinyl)-1,3,5-triazine are described in Japan Patent 74 46635.
  • Other preparation methods for the novel compounds of formula (ix) are described in Mendoza, C.E. et al., J. Ag. Food Chem., 19, (1), 41-45 (1972).
  • novel heterocyclic nitrogen-containing compounds of formula (x) can be prepared by the following general reaction scheme:
  • novel heterocyclic nitrogen-containing compounds of formula (xi) can be prepared by the following general reaction scheme:
  • R 33 , g, X 20 , Y 52 , Y 53 and Y 49 are as defined hereinabove.
  • Reactions of this general type for preparing substituted 1,3,5-triazines including process conditions and intermediate preparations are similar to the procedures employed for preparing compounds of formula (viii) above.
  • Other preparation methods for the novel compounds of formula (xi) are described in Allen, C.F.H. and Converse, S., Org. Syn. Coll., Vol. I, 226-227, U.S. Patent 1,911,689, Bessiere-Chretien, Y. and Serne, H., Bull. Soc. Chim. France. (6).
  • novel heterocyclic nitrogen-containing compounds of formula (xii) can be prepared by the following general reaction scheme:
  • novel heterocyclic nitrogen-containing compounds of formula (xiii) can be prepared by the following general reaction scheme:
  • novel heterocyclic nitrogen-containing compounds of formula (xiv) can be prepared by the following general reaction scheme:
  • R 37 , R 38 , B 14 and Y 47 are as defined hereinabove.
  • Reactions of this general type for preparing substituted azoles including process conditions and intermediate preparations are described in Pahanayak, B.K., J. Ind. Chem. Soc., 55, (3), 264-267 (1978) and Young. T.E. and Amstutz, E.D., J. Amer. Chem. Soc., 73, 4773-4775. (1951).
  • Other preparation methods for the novel compounds of formula (xiv) are described by Tripathi, H. et al., Agric. Biol. Chem., 37, 1375 (1973) and Young, T.E. and Amstutz, E.D., J. Amer. Chem. Soc. 73, 4773-4775 (1951).
  • novel heterocyclic nitrogen-containing compounds of formula (xv) can be prepared by the following general reaction scheme:
  • R 41 , R 42 , and B 15 are as defined hereinabove.
  • Reactions of this general type for preparing substituted 1,2,4-azoles including process conditions and intermediate preparations are described by Selim, M. and Selim, M. , Bull. Soc. Chim. France. 1219-1220 (1967).
  • novel heterocyclic nitrogen-containing compounds of formula (xvi) can be prepared by the following general reaction scheme:
  • novel heterocyclic nitrogen-containing compounds of formula (xvii) can be prepared by the following general reaction scheme:
  • novel heterocyclic nitrogen-containing compounds of formula (xviii) can be prepared by the following general reaction scheme:
  • R 50 , B 17 , Y 54 , Y 55 and Y 49 are as defined hereinabove.
  • Reactions of this general type for preparing substituted 1,3,5-triazines including process conditions and intermediate preparations are similar to the procedures employed for preparing compounds of formula (viii) above.
  • Other preparation methods for the novel compounds of formula (xix) are described by Beech, W.F., J. Chem. Soc., (C), 466-472 (1967).
  • novel heterocyclic nitrogen-containing compounds of formula (xx) can be prepared by the following general reaction scheme:
  • 1,3,5-triazines including process conditions and intermediate preparations are similar to the procedures employed for preparing compounds of formula (viii) above.
  • novel heterocyclic nitrogen-containing compounds of formula (xxi) can be prepared by the following general reaction scheme:
  • novel heterocyclic nitrogen-containing compounds of formula (xxii) can be prepared by "the following general reaction scheme:
  • R 53 , X 25 , Y 60 , Y 61 and Y 49 are as defined hereinabove. Reactions of this general type for preparing substituted 1,3,5-triazines including process conditions and intermediate preparations are similar to the procedures employed for preparing compounds of formula (viii) above.
  • novel heterocyclic nitrogen-containing compounds of formula (xxiii) can be prepared by the following general reaction scheme:
  • R 54 , X 26 , Y 50 and Y 51 are as defined hereinabove. Reactions of this general type for preparing hexahydro-1,3,5-triazines including process conditions are described for example by
  • novel heterocyclic nitrogen-containing compounds of formula (xxiv) can be prepared by the following general reaction scheme:
  • novel heterocyclic nitrogen-containing compounds of formula (xxvi) can be prepared by the following general reaction scheme:
  • novel heterocyclic nitrogen-containing compounds of formula (xxvii) can be prepared by the following general reaction scheme:
  • novel heterocyclic nitrogen-containing compounds of formula (xxviii) can be prepared by the following general reaction scheme:
  • novel heterocyclic nitrogen-containing compounds of formula (xxix) can be prepared by the following general reaction scheme:
  • Suitable halogenating agents include, for example, PCL 5 , POCl 3 , PBr 5 and POBr 3 and mixtures thereof.
  • Reactions of this general type for preparing substituted pyridazinones including process conditions and intermediate preparations are described for example in Yuki Gosei Kagaku Kyotai Shi 28, (4), 462-463 (1970).
  • Other preparation methods for the novel compounds of formula (xxix) are described in Yakugaku Zasshi 86, (12), 1168-1172 (1966), Acta Dol. Pharm.
  • novel heterocyclic nitrogen-containing compounds of formula (xxx) can be prepared by the following general reaction scheme:
  • novel heterocyclic nitrogen-containing compounds of formula (xxxi) can be prepared by the following general reaction scheme:
  • R 74 , X 33 , Z 13 , Y 83 , Y 84 AND Y 85 are as defined hereinabove. Reactions of this general type for preparing substituted pyridazinones including process conditions and intermediate preparations are similar to the procedures employed for preparing compounds of formula (xxix) above.
  • novel heterocyclic nitrogen-containing compounds of formula (xxxii) can be prepared by the following general reaction scheme:
  • novel heterocyclic nitrogen-containing compounds of formula (xxxiii) can be prepared by the following general reaction scheme:
  • the antitranspirant compounds of formula 1 have been found to significantly reduce plant and crop usage of water, i.e., reduce transpiration rate, and increase the resistance of plant leaf surfaces to the loss of moisture vapor, i.e., increase diffusive resistance.
  • the antitranspirant compounds used in this invention are substantially non-inhibiting of photosynthetic light-requiring reactions, substantially non-phytotoxic to growing plants and serve to increase crop yields in comparison with untreated crops at similar conditions, especially in regions where plants are subject to moisture stress conditions.
  • the antitranspirant compounds used in this invention provide for the conservation of soil moisture by reducing plant and crop usage of water during certain development periods, e.g., vegetative period, thereby making the unused water available at other periods of plant or crop development, e.g., reproductive growth period.
  • stomata are minute openings in the epidermis of plant leaf surfaces through which occurs gaseous interchange between the atmosphere and the intercellular spaces within the leaf. It is believed that the antitranspirant compounds of formula 1 effectively reduce the transpiration rate in plants by closing plant stomata or constricting plant stomatal openings to such a degree that moisture loss is reduced and, in addition, the compounds exhibit substantially no detrimental effect on photosynthetic electron flow.
  • the photosynthetic process in plants consists of light-requiring reactions, i.e., light reactions, and non-light-requiring reactions, i.e., dark reactions.
  • the dark reactions in general involve a complex of enzyme-mediated reactions which provide for the conversion of carbon dioxide to sugar.
  • Photosystem I and Photosystem II Two light-requiring reactions are involved in plant photosynthesis and are conventionally termed Photosystem I and Photosystem II. See. for example, Salisbury. F.B. and Ross, C.W., Plant Physiology, pp. 131-135 (1978). These photosystems are interconnected by an electron transport chain, and provide reducing power and chemical energy to the dark reactions. Inhibition of either or both of these photosystems can detrimentally affect photosynthesis, thereby causing plant injury or even plant death.
  • the antitranspirant compounds used in this invention have been found to cause no or substantially no inhibition of Photosystem I or Photosystem II.
  • the herbicide atrazine is known to substantially inhibit the light reactions of photosynthesis, particularly the electron transport chain. See, for example, Jachetta, J.J. and Radosevich, S.R., Weed Science 29: 37-43 (1981).
  • Such herbicidal inhibition leads to a buildup of carbon dioxide within the leaf which causes closure of the stomates.
  • the antitranspirant activity of atrazine is associated with its herbicidal properties.
  • substantially no inhibition of photosynthetic electron transport refers to no or little inhibition of photosynthetic electron transport.
  • an effective amount of a heterocyclic nitrogen-containing compound for reducing moisture loss from plants refers to an antitranspirationally effective amount of the compound sufficient to reduce transpirational moisture loss from plants without substantially inhibiting plant photosynthetic electron transport.
  • an effective amount of a heterocyclic nitrogen-containing compound for increasing crop yield refers to a yield enhancing effective amount of the compound sufficient to increase crop yield without sustantially inhibiting plant photosynthetic electron transport.
  • the effective amount of compound can vary over a wide range depending on the particular compound employed, the particular crop to be treated, environmental and climatic conditions, and the like, provided that the amount of compound used does not cause substantial inhibition of plant photosynthetic electron transport or substantial phytotoxicity, e.g., foliar burn, chlorosis or necrosis, to the plant.
  • the compound can preferably be applied to plants and crops at a concentration of from about 0.25 to 15 pounds of compound per acre as more fully described below.
  • heterocyclic nitrogen-containing compounds contemplated by formula 1 may be employed according to a variety of conventional methods known to those skilled in the art.
  • Compositions containing the compounds as the active ingredient will usually comprise a carrier and/or diluent, either liquid or solid.
  • Suitable liquid diluents or carriers include water, petroleum distillates, or other liquid carriers with or without surface active agents.
  • Liquid concentrates may be prepared by dissolving one of these compounds with a nonphytotoxic solvent such as acetone, xylene, nitrobenzene, cyclohexanone or dimethylformamide and dispersing the active ingredients in water with the aid of suitable surface active emulsifying and dispersing agents.
  • dispersing and emulsifying agents are dictated by the nature of the composition and the ability of the agent to facilitate the dispersion of the active ingredient. Generally, it is desirable to use as little of the agent as is possible, consistent with the desired dispersion of the active ingredient in the spray so that rain does not re-emulsify the active ingredient after it is applied to the plant and wash it off the plant.
  • Nonionic, anionic. or cationic dispersing and emulsifying agents may be employed, for example, the condensation products of alkylene oxides with phenol and organic acids, alkyl aryl sulfonates, complex ether alcohols, quaternary ammonium compounds, and the like.
  • the active ingredient is dispersed in and on an appropriately divided solid carrier such as clay, talc, bentonite, diatomaceous earth, fuller's earth, and the like.
  • an appropriately divided solid carrier such as clay, talc, bentonite, diatomaceous earth, fuller's earth, and the like.
  • the aforementioned dispersing agents as well as lignosulfonates can be included.
  • the required amount of the active ingredient contemplated herein may be applied per acre treated in from 1 to 200 gallons or more of liquid carrier and/or diluent or in from about 5 to 500 pounds of inert solid carrier and/or diluent.
  • concentration in the liquid concentrate will usually vary from about 5 to 95 percent by weight and in the solid formulations from about 0.5 to about 90 percent by weight.
  • Satisfactory sprays or dusts for general use contain from about 0.1 to about 100 pounds of active ingredient per acre, preferably from about 0.25 to about 15 pounds of active ingredient per acre, and more preferably from about 0.5 to about 5 pounds of active ingredient per acre.
  • Formulations useful in the conduct of this invention can also contain other optional ingredients such as stabilizers or other biologically active compounds, insofar as they do not impair or reduce the activity of the active ingredient and do not harm the plant being treated.
  • Other biologically active compounds include, for example, one or more insecticidal, herbicidal, fungicidal, nematicidal, miticidal, plant growth regulators or other known compounds. Such combinations may be used for the known or other purpose of each ingredient and may provide a synergistic effect.
  • the antitranspirant compounds of formula l. are preferably applied to plants and crops under substantially little or no water stress conditions, or what can be considered as average or normal growing conditions.
  • a preferred condition for compound application is prior to substantial soil moisture loss. While not wishing to be bound to any particular theory, it is believed that application of the antitranspirant compounds does not result in a reduction of the minimum total water requirements of a treated plant or crop, but rather the application of such compounds serves to promote more efficient water utilization by treated plants and crops.
  • the antitranspirant effect does not reduce the total amount of water needed to grow a given plant or crop except for water savings which may be realized for some crops under irrigation, but rather such antitranspirant effect is manifested by an increase in yield of treated crops having no or limited irrigation and rainfall in comparison with untreated crops at similar conditions.
  • the antitranspirant compounds of formula 1 are preferably applied to plants and crops under conditions which favor large gradients in water vapor pressure between the saturated atmosphere within the leaf and the atmosphere around the leaf. Such conditions include low atmospheric humidity, high light/heat loads on the leaf, and high rates of air movement.
  • the application of the antitranspirant compounds of formula 1 to plants reduces the amount of water utilized by the plane for on the order of about a 1 to 6 week period and therefore provides for a greater amount of reserve water available in the soil during other developmental periods such as the critical reproductive growth phase.
  • This soil moisture conservation can minimize any water deficit within plant tissues during critical developmental periods such as the reproductive growth phase resulting in increased crop yield.
  • the antitranspirant compounds used in this invention may likewise be applied during the plant reproductive growth phase to obtain similar results.
  • the antitranspirant compounds of formula 1 are useful for decreasing irrigation water requirements especially in dry climate regions, for protecting plants from wilting or other damage during transplantation or shipment or during severe cold weather, and for alleviating water stress in certain types of environments as indicated above.
  • Such compounds are useful in agriculture, horticulture and related fields and can be applied to vegetation such as non-deciduous ornamental shrubs, evergreens, trees, and the like, to protect them against winter kill.
  • a chief cause of winter kill is an excessive loss of moisture from leaf surfaces on sunny or windy days when the ground is frozen and the root systems cannot replace the water loss.
  • the antitranspirant compounds can also be applied to other ornamentals such as roses and other flowers, Christmas trees, and the like, to preserve freshness and retard needle drop.
  • the antitranspirant compounds can further be used in avoiding or minimizing the effects of summer scald and transplant shock.
  • antitranspirant compounds of formula 1 may also be used to control foliar diseases on crops such as wheat and oats. See, for example, Avant Gardener, Vol. 18, No. 1, November, 1985, in which antitranspirants are used to control fungus diseases.
  • plants refer in general to any agronomic or horticultural crops, ornamentals and turfgrasses.
  • Illustrative of plants which may be treated by the antitranspirant compounds of formula 1 according to the method of this invention include, for example, corn, cotton, sweet potatoes, white potatoes, alfalfa, wheat, rye, upland rice, barley, oats, sorghum, dry beans, soybeans, sugar beets, sunflowers, tobacco, tomatoes, canola, deciduous fruit, citrus fruit, tea, coffee, olives, pineapple, cocoa, banana, sugar cane, oil palm, herbaceous bedding plants, woody shrubs, turfgrasses, ornamental plants, evergreens, trees, flowers, and the like.
  • crops refer in general to any of the illustrative agronomic or horticultural crops above.
  • Transplanted stock refers in general to tobacco, tomatoes, eggplant, cucumbers, lettuce, strawberries, herbaceous bedding plants, woody shrubs, tree seedlings and the like.
  • the antitranspirant compounds contemplated herein reduce transpirational moisture loss from plants and increase crop yields.
  • Such compounds have a high margin of safety in that when used in sufficient amount to provide an antitranspirant effect or yield enhancing effect, they do not inhibit plant photosynthetic electron transport or burn or injure, the plant, and they resist weathering which includes wash-off caused by rain, decomposition by ultraviolet light, oxidation, or hydrolysis in the presence of moisture or, at least, such decomposition, oxidation, and hydrolysis as would materially decrease the desirable antitranspirant characteristic of the active ingredient or impart undesirable characteristics, for instance, phytotoxicity, to the active ingredients.
  • Mixtures of the active compounds may be employed if desired as well as combinations of the active compounds with other biologically active compounds or ingredients as indicated above.
  • Compound 48 This compound is referred to hereinafter as Compound 48.
  • Example VIII In a manner similar to Example VIII, 4.63 grams (0.04 mole) of 2-chloroaniline and 6.69 grams (0.04 mole) of cyanuric chloride were reacted in the presence of 3.89 grams (0.04 mole) of 2,6-lutidine except that the cooling bath was removed at the end of the feed period and the stirred mixture allowed to warm to room temperature. After filtering off lutidine hydrochloride, the filtrate was freed of acetone solvent under reduced pressure and the resulting solid was crystallized from a mixture of hexane and benzene.
  • This compound is referred to hereinafter as Compound 66.
  • Example XIV Into a solution containing 600 milligrams (0.002 mole) of 4,6-dichloro-2-(4'-nitrophenylamino)-1,3,5-triazine prepared in Example XIV in 300 milliliters of CH 2 Cl 2 was bubbled HBr gas at room temperature for a period of 4 hours. The resulting mixture was stored in a refrigerator for about 48 hours and an oil, which separated from CH 2 Cl 2 , was collected by decantation.
  • This compound is referred to hereinafter as Compound 67.
  • This compound is referred to hereinafter as Compound 68.
  • Compound 70 This compound is referred to hereinafter as Compound 70.
  • This compound is referred to hereinafter as Compound 71.
  • This compound is referred to hereinafter as Compound 73.
  • Part B Preparation of 2,4-dichloro-6- (4'-sec-butyloxyphenoxy)-1,3,5-triazine Into a 100 mill iliter 3-necked round bottom f lask equipped with a thermometer, addition funnel and nitrogen inlet was added cyanuric chloride (2.22 grams, 0.01 mole) dissolved in 20 milliliters of acetone. After cooling to a temperature of 0-5oC, 4-(sec-butyloxy) phenol (2.0 grams, 0.01 mole) prepared in Part A and 2,6-lutidine (1.40 milliliters, 0.01 mole) dissolved in 20 milliliters of acetone were slowly added dropwise via the addition funnel.
  • the temperature of the reaction was maintained between 0-5oC during the addition.
  • the reaction mixture was then stirred at room temperature for a period of 16 hours. After this period, the reaction mixture was filtered through a Celite pad and the pad rinsed with acetone. Ice-water was added and the oil which precipitated was extracted with EtOAc. The EtOAc layers were washed with water, dried (MgSO 4 ) and cpncentrated to give a brown semi-solid.
  • This compound is referred to hereinafter as Compound 74.
  • Example XXIV Into a solution containing 2.0 grams (0.007 mole) of 4-chloro-6-methyl-2-(2',4'-dichlorophenoxy)-1,3,5-triazine prepared in Example XXIV in 300 milliliters of CH 2 Cl 2 was bubbled dry HBr gas for a period of 3 hours. The mixture was allowed to stand at room temperature for about 18 hours. The suspension was then filtered and the solids partitioned between NaHCO solution and CH 2 Cl 2 .
  • This compound is referred to hereinafter as Compound 88.
  • Example XXVIII The column chromatography fractions from Example XXVIII were examined and a group identified as containing 4-chloro-6-(2',2',2'-trifluoroethoxy)-2-phenyl-1,3,5-triazine as a second component. These were combined and purified by preparative liquid chromatography (silica gel) using 10% ethyl acetate in hexane as the eluent to give 320 milligrams (0.001 mole) of 4-chloro-6-(2',2',2'-trifluoroethoxy)-2-phenyl-1,3,5-triazine as an oil. Elemental analysis of the product indicated the following:
  • Compound 90 This compound is referred to hereinafter as Compound 90.
  • This compound is referred to hereinafter as Compound 92.
  • Example XXXII In a manner similar to that employed in Example XXXII, other compounds were prepared.
  • reaction mixture was then diluted with 150 milliliters of water and extracted with CH 2 Cl 2
  • 2,4-Dichlorobenzaldehyde oxime prepared in Part A was reacted with cyanuric chloride using a procedure similar to that described in Example XXXII above.
  • the reaction mixture was filtered to remove the precipitate and the filtrate was poured onto ice causing a yellow solid to form.
  • the solid was separated and recrystallized from acetone-water to yield 2.1 grams (0.006 mole) of 2,4-dichlorobenzaldehyde O-(4, 6-dichloro-1,3,5-triazin- 2-yl)oxime as pale yellow needles having a melting point of 124°C-124.5°C. Elemental analysis of the product indicated the following:
  • This compound is referred to hereinafter as Compound 96.
  • the compound is referred to hereinafter as Compound 97.
  • This compound is referred to hereinafter as Compound 98.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Environmental Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Toxicology (AREA)
  • Pest Control & Pesticides (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

Procédé permettant de réduire les pertes d'humidité par la transpiration chez les plantes et d'augmenter le rendement des récoltes en appliquant sur la surface des plantes ou sur les récoltes une quantité efficace d'un composé hétérocyclique contenant de l'azote. Cette invention concerne également de nouveaux composés hétérocycliques contenant de l'azote ainsi que des procédés pour leur préparation.
PCT/US1987/000240 1986-01-23 1987-01-23 Utilisation de composes heterocycliques contenant de l'azote pour reduire la perte d'humidite des plantes et augmenter le rendement des recoltes Ceased WO1987004321A2 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
HU871236A HUT45848A (en) 1986-01-23 1987-01-23 Applications of heterocyclic nitrogen-containing compounds for reducing water loss of plants and for increasing crop yield
FI874111A FI874111A7 (fi) 1986-01-23 1987-01-23 Heterosyklisten typpeä sisältävien yhdisteiden käyttö kosteuden haiht umisen vähentämiseen kasveista ja satotuloksen lisäämiseen.
BR8705356A BR8705356A (pt) 1986-01-23 1987-01-23 Processo para a preparacao de composicoes agroquimicas para diminuir a perda de agua pelas plantas devido a transpiracao,contendo derivados heterociclicos azotados hexagonais ou pentagonais substituidos
KR870700857A KR880700635A (ko) 1986-01-23 1987-09-22 식물의 수분 손실를 감소시키고 농작물의 수확을 증가시키기 위한 헤테로사이클릭 질소-함유 화합물의 용도
DK496187A DK496187D0 (da) 1986-01-23 1987-09-22 Heterocycliske nitrogenholdige forbindelser samt disses anvendelse til formindskelse af fugtighedstab fra planter og foroegelse af afgroedeudbytte

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US82438986A 1986-01-23 1986-01-23
US824,389 1986-01-23
US93941686A 1986-12-15 1986-12-15
US939,416 1986-12-15

Publications (2)

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WO1987004321A2 true WO1987004321A2 (fr) 1987-07-30
WO1987004321A3 WO1987004321A3 (fr) 1987-11-05

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Country Status (12)

Country Link
EP (1) EP0258391A1 (fr)
KR (1) KR880700635A (fr)
AU (1) AU7031687A (fr)
DK (1) DK496187D0 (fr)
FI (1) FI874111A7 (fr)
GR (1) GR870094B (fr)
IL (1) IL81307A0 (fr)
OA (1) OA08675A (fr)
PT (1) PT84183B (fr)
TN (1) TNSN87008A1 (fr)
WO (1) WO1987004321A2 (fr)
ZW (1) ZW1287A1 (fr)

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EP0776894A4 (fr) * 1994-08-02 1997-11-05 Nippon Soda Co Derive d'oxazole, son procede de production et herbicide
US6184225B1 (en) 1996-02-13 2001-02-06 Zeneca Limited Quinazoline derivatives as VEGF inhibitors
US6265411B1 (en) 1996-05-06 2001-07-24 Zeneca Limited Oxindole derivatives
US6291455B1 (en) 1996-03-05 2001-09-18 Zeneca Limited 4-anilinoquinazoline derivatives
US6294532B1 (en) 1997-08-22 2001-09-25 Zeneca Limited Oxindolylquinazoline derivatives as angiogenesis inhibitors
WO2003024939A3 (fr) * 2001-08-28 2003-10-02 Gen Electric Composes de triazine, polymeres comprenant des unites structurelles de triazine, et methode associee
US6638945B1 (en) 1999-05-08 2003-10-28 Astrazeneca Ab Quinoline derivatives as inhibitors of MEK enzymes
US6673803B2 (en) 1996-09-25 2004-01-06 Zeneca Limited Quinazoline derivatives and pharmaceutical compositions containing them
US6809097B1 (en) 1996-09-25 2004-10-26 Zeneca Limited Quinoline derivatives inhibiting the effect of growth factors such as VEGF
US6809106B1 (en) 1999-05-08 2004-10-26 Astrazeneca Ab Quinoline derivatives as inhibitors of MEK enzymes
US6887874B2 (en) 2000-08-09 2005-05-03 Astrazeneca Ab Cinnoline compounds
US7074800B1 (en) 1999-02-10 2006-07-11 Astrazeneca Ab Quinazoline derivatives as angiogenesis inhibitors
US7160889B2 (en) 2000-04-07 2007-01-09 Astrazeneca Ab Quinazoline compounds
US7173038B1 (en) 1999-11-05 2007-02-06 Astrazeneca Ab Quinazoline derivatives as VEGF inhibitors
US7262201B1 (en) 1998-10-08 2007-08-28 Astrazeneca Ab Quinazoline derivatives
US7268230B2 (en) 2002-02-01 2007-09-11 Astrazeneca Ab Quinazoline compounds
US7371765B2 (en) 2000-08-09 2008-05-13 Astrazeneca Ab Quinoline derivatives having VEGF inhibiting activity
WO2010126270A1 (fr) * 2009-04-29 2010-11-04 Dow Advanced Display Materials,Ltd. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant
US7906608B2 (en) 2005-07-15 2011-03-15 Jsr Corporation Nitrogenated aromatic compound, process for production of the same, polymer, and proton conductive membrane
WO2011095441A1 (fr) 2010-02-02 2011-08-11 Bayer Materialscience Ag Formulation de photopolymère comprenant des monomères d'enregistrement à base de triazine
CN103290678A (zh) * 2013-04-13 2013-09-11 李美凤 一种用于纺织品抗菌整理剂
US8859570B2 (en) 2003-12-24 2014-10-14 Astrazeneca Ab Maleate salts of a quinazoline derivative useful as an antiangiogenic agent
WO2015140792A1 (fr) * 2014-03-16 2015-09-24 Hadasit Medical Research Services And Development Ltd. Inhibiteurs de la désiodinase de type iii et leurs utilisations
US9717245B2 (en) 2013-02-07 2017-08-01 Sundaresan Subramanyam Total foliar product for agriculture / horticulture / tissue culture and hydroponic cultivation
WO2020069056A1 (fr) 2018-09-27 2020-04-02 Fmc Corporation Intermédiaires pour préparer des pyridazinones herbicides
EP3567035B1 (fr) * 2007-04-11 2022-06-01 CanBas Co., Ltd. Composés de 2,5-doxo-azoline n-substituée présentant une activité anticancéreuse

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1419632A (en) * 1972-04-11 1975-12-31 Ici Ltd Hydroxyphenoxy-s-triazine derivatives

Cited By (39)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0776894A4 (fr) * 1994-08-02 1997-11-05 Nippon Soda Co Derive d'oxazole, son procede de production et herbicide
US6107251A (en) * 1994-08-02 2000-08-22 Nippon Soda Co., Ltd. Oxazole derivative, process for producing the same, and herbicide
US6184225B1 (en) 1996-02-13 2001-02-06 Zeneca Limited Quinazoline derivatives as VEGF inhibitors
US6291455B1 (en) 1996-03-05 2001-09-18 Zeneca Limited 4-anilinoquinazoline derivatives
US6265411B1 (en) 1996-05-06 2001-07-24 Zeneca Limited Oxindole derivatives
US6809097B1 (en) 1996-09-25 2004-10-26 Zeneca Limited Quinoline derivatives inhibiting the effect of growth factors such as VEGF
US6673803B2 (en) 1996-09-25 2004-01-06 Zeneca Limited Quinazoline derivatives and pharmaceutical compositions containing them
USRE42353E1 (en) 1996-09-25 2011-05-10 Astrazeneca Uk Limited Quinazoline derivatives and pharmaceutical compositions containing them
US6897210B2 (en) 1996-09-25 2005-05-24 Zeneca Limited Quinazoline derivatives and pharmaceutical compositions containing them
US6294532B1 (en) 1997-08-22 2001-09-25 Zeneca Limited Oxindolylquinazoline derivatives as angiogenesis inhibitors
US7262201B1 (en) 1998-10-08 2007-08-28 Astrazeneca Ab Quinazoline derivatives
US8492560B2 (en) 1999-02-10 2013-07-23 Astrazeneca Ab Quinazoline derivatives as angiogenesis inhibitors
US7074800B1 (en) 1999-02-10 2006-07-11 Astrazeneca Ab Quinazoline derivatives as angiogenesis inhibitors
US6809106B1 (en) 1999-05-08 2004-10-26 Astrazeneca Ab Quinoline derivatives as inhibitors of MEK enzymes
US6638945B1 (en) 1999-05-08 2003-10-28 Astrazeneca Ab Quinoline derivatives as inhibitors of MEK enzymes
US7173038B1 (en) 1999-11-05 2007-02-06 Astrazeneca Ab Quinazoline derivatives as VEGF inhibitors
US9040548B2 (en) 1999-11-05 2015-05-26 Astrazeneca Ab Quinazoline derivatives as VEGF inhibitors
US8642608B2 (en) 1999-11-05 2014-02-04 Astrazeneca Ab Quinazoline derivatives as VEGF inhibitors
US10457664B2 (en) 1999-11-05 2019-10-29 Genzyme Corporation Quinazoline derivatives as VEGF inhibitors
US7160889B2 (en) 2000-04-07 2007-01-09 Astrazeneca Ab Quinazoline compounds
US7371765B2 (en) 2000-08-09 2008-05-13 Astrazeneca Ab Quinoline derivatives having VEGF inhibiting activity
US6887874B2 (en) 2000-08-09 2005-05-03 Astrazeneca Ab Cinnoline compounds
WO2003024939A3 (fr) * 2001-08-28 2003-10-02 Gen Electric Composes de triazine, polymeres comprenant des unites structurelles de triazine, et methode associee
US8293902B2 (en) 2002-02-01 2012-10-23 Astrazeneca Ab Quinazoline compounds
US7268230B2 (en) 2002-02-01 2007-09-11 Astrazeneca Ab Quinazoline compounds
US9890140B2 (en) 2003-12-24 2018-02-13 Astrazeneca Ab Maleate salts of a quinazoline derivative useful as an antiangiogenic agent
US8859570B2 (en) 2003-12-24 2014-10-14 Astrazeneca Ab Maleate salts of a quinazoline derivative useful as an antiangiogenic agent
US9556151B2 (en) 2003-12-24 2017-01-31 Astrazeneca Ab Maleate salts of a quinazoline derivative useful as an antiangiogenic agent
US7906608B2 (en) 2005-07-15 2011-03-15 Jsr Corporation Nitrogenated aromatic compound, process for production of the same, polymer, and proton conductive membrane
EP3567035B1 (fr) * 2007-04-11 2022-06-01 CanBas Co., Ltd. Composés de 2,5-doxo-azoline n-substituée présentant une activité anticancéreuse
WO2010126270A1 (fr) * 2009-04-29 2010-11-04 Dow Advanced Display Materials,Ltd. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant
WO2011095441A1 (fr) 2010-02-02 2011-08-11 Bayer Materialscience Ag Formulation de photopolymère comprenant des monomères d'enregistrement à base de triazine
US9717245B2 (en) 2013-02-07 2017-08-01 Sundaresan Subramanyam Total foliar product for agriculture / horticulture / tissue culture and hydroponic cultivation
CN103290678A (zh) * 2013-04-13 2013-09-11 李美凤 一种用于纺织品抗菌整理剂
CN103290678B (zh) * 2013-04-13 2015-07-22 徐茂航 一种用于纺织品抗菌整理剂
US10435365B2 (en) 2014-03-16 2019-10-08 Hadasit Medical Research Services And Development Ltd. Type III deiodinase inhibitors and uses thereof
WO2015140792A1 (fr) * 2014-03-16 2015-09-24 Hadasit Medical Research Services And Development Ltd. Inhibiteurs de la désiodinase de type iii et leurs utilisations
US11091434B2 (en) 2014-03-16 2021-08-17 Hadasit Medical Research Services And Development Ltd. Type III deiodinase inhibitors and uses thereof
WO2020069056A1 (fr) 2018-09-27 2020-04-02 Fmc Corporation Intermédiaires pour préparer des pyridazinones herbicides

Also Published As

Publication number Publication date
IL81307A0 (en) 1987-08-31
EP0258391A1 (fr) 1988-03-09
GR870094B (en) 1988-09-28
PT84183B (pt) 1989-09-14
KR880700635A (ko) 1988-04-11
DK496187A (da) 1987-09-22
TNSN87008A1 (fr) 1990-01-01
FI874111A0 (fi) 1987-09-21
AU7031687A (en) 1987-08-14
FI874111L (fi) 1987-09-21
DK496187D0 (da) 1987-09-22
OA08675A (fr) 1989-03-31
FI874111A7 (fi) 1987-09-21
PT84183A (pt) 1987-02-01
ZW1287A1 (en) 1987-10-28
WO1987004321A3 (fr) 1987-11-05

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