US2017050957A1PendingUtilityA1
4-amino-6-(heterocyclic)picolinates and 6-amino-2-(heterocyclic)pyrimidine-4-carboxylates and their use as herbicides
Est. expiryMar 15, 2033(~6.7 yrs left)· nominal 20-yr term from priority
Inventors:Joseph D. EckelbargerJeffrey B. EppStephen Craig FieldsLindsey G. FischerNatalie C. GiampietroKatherine A. GuenthenspbergerChristian T. LoweJeff PetkusJoshua RothNorbert M. SatchiviPaul R. SchmitzerThomas L. SiddallNick X. Wang
C07D 405/04C07D 417/04A01N 43/56A01N 43/76A01N 43/78A01N 43/647C07D 403/04C07D 409/04A01N 43/54A01N 43/52A01N 43/80C07D 413/04C07D 401/04A01N 43/40C07F 7/0803A01N 55/00A01N 43/12C07D 213/803C07D 213/79
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Claims
Abstract
4-Amino-6-(heterocyclic)picolinic acids and their derivatives; 6-amino-2-(heterocyclic)pyrimidine-4-carboxylates and their derivatives; and methods of using the same as herbicides.
Claims
exact text as granted — not AI-modified1 - 32 . (canceled)
33 . A compound of the Formula (I):
wherein
X is N or CY, wherein Y is hydrogen, halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, or C 1 -C 3 haloalkylthio;
R 1 is OR 1′ or N R1″ R 1′″ , wherein R 1′ is hydrogen, C 1 -C 8 alkyl, or C 7 -C 10 arylalkyl, and R 1″ and R 1′″ are independently hydrogen, C 1 -C 12 alkyl, C 3 -C 12 alkenyl, or C 3 -C 12 alkynyl;
R 2 is halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, amino, C 1 -C 4 alkylamino, C 2 -C 4 haloalkylamino, formyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, cyano, or a group of the formula —CR 17 ═CR 18 —SiR 19 R 20 R 21 , wherein R 17 is hydrogen, F, or Cl; R 18 is hydrogen, F, Cl, C 1 -C 4 alkyl, or C 1 -C 4 haloalkyl; and R 19 , R 20 , and R 21 are independently C 1 -C 10 alkyl, C 3 -C 6 cycloalkyl, phenyl, substituted phenyl, C 1 -C 10 alkoxy, or OH;
R 3 and R 4 are independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alknyl, formyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbamyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 trialkylsilyl, C 1 -C 6 dialkylphosphonyl, or R 3 and R 4 taken together with N is a 5- or 6-membered saturated ring, or R 3 and R 4 taken together represent ═CR 3′ (R 4′ ), wherein R 3′ and R 4′ are independently hydrogen, C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alknyl, C 1 -C 6 alkoxy or C 1 -C 6 alkylamino, or, R 3′ and R 4′ taken together with ═C represent a 5- or 6-membered saturated ring;
A is one of groups A1, A2, A13, A14, or A21 to A24
R 5 is hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino, C 2 -C 4 haloalkylamino, OH, or CN;
R 6 and R 6′ are independently hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino or C 2 -C 4 haloalkylamino, OH, CN, or NO 2 ; and
R 7 and R 7′ are independently hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino, C 2 -C 4 haloalkylamino, or phenyl;
or an N-oxide or salt thereof.
34 . A compound of the Formula (I):
wherein
X is N, CH, CF, CCl, or CBr;
R 1 is OR 1′ , wherein R 1′ is hydrogen or C 1 -C 4 alkyl;
R 2 is chlorine;
R 3 and R 4 are hydrogen;
A is one of groups A1, A2, A13, or A14
R 5 is hydrogen, halogen, OH, amino, CN, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 alkylamino, or cyclopropyl;
R 6 and R 6′ are independently hydrogen, halogen, OH, NH 2 , CN, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, cyclopropyl, or vinyl; and
R 7 and R 7′ are independently hydrogen, halogen, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, cyclopropyl, C 1 -C 3 alkylamino, or phenyl;
or an N-oxide or salt thereof.
35 . A herbicidal composition, comprising a herbicidally effective amount of at least one compound as claimed in claim 34 .
36 . The herbicidal composition as claimed in claim 35 , in a mixture with at least one formulation auxiliary.
37 . The herbicidal composition as claimed in claim 35 , comprising at least one further pesticidally active compound selected from the group consisting of insecticides, acaricides, herbicides, fungicides, safeners and growth regulators.
38 . The herbicidal composition as claimed in claim 37 , comprising a safener.
39 . The herbicidal composition as claimed in claim 38 , comprising a further herbicide.
40 . A method for controlling an unwanted plant, comprising applying an effective amount of at least one compound as claimed in claim 34 , to a plant and/or on a site of unwanted plant growth.
41 . A compound as claimed in claim 34 , wherein said compound is capable of being used for controlling an unwanted plant in a plant crop.
42 . A compound as claimed in claim 41 , wherein the plant crop is a transgenic plant crop.
43 . A method for controlling an unwanted plant, comprising applying an effective amount of a herbicidal composition as claimed in claim 35 , to a plant and/or on a site of unwanted plant growth.
44 . A compound as claimed in claim 34 , wherein
A represents
X is N, CH, CF, CCl, or CBr;
R 1 is OR 1′ , wherein R 1′ is hydrogen or C 1 -C 4 alkyl;
R 2 is chlorine;
R 3 and R 4 are hydrogen;
R 5 is hydrogen, halogen, OH, amino, CN, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 alkylamino, or cyclopropyl;
R 6 and R 6′ are independently hydrogen, halogen, OH, NH 2 , CN, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, cyclopropyl, or vinyl; and
R 7 and R 7′ are independently hydrogen, halogen, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, cyclopropyl, C 1 -C 3 alkylamino, or phenyl;
or an N-oxide or salt thereof.
45 . A compound as claimed in claim 44 having the formula
wherein
R 1 is hydrogen or C 1 -C 4 alkyl;
R 5 is hydrogen;
R 6 is hydrogen or halogen;
R 6′ is hydrogen; and
R 7 and R 7′ are hydrogen;
or an N-oxide or salt thereof.
46 . A compound as claimed in claim 34 , wherein
A represents
X is N, CH, CF, CCl, or CBr;
R 1 is OR 1′ , wherein R 1′ is hydrogen or C 1 -C 4 alkyl;
R 2 is chlorine;
R 3 and R 4 are hydrogen;
R 5 is hydrogen, halogen, OH, amino, CN, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 alkylamino, or cyclopropyl;
R 6 and R 6′ are independently hydrogen, halogen, OH, NH 2 , CN, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, cyclopropyl, or vinyl; and
R 7 and R 7′ are independently hydrogen, halogen, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, cyclopropyl, C 1 -C 3 alkylamino, or phenyl;
or an N-oxide or salt thereof.
47 . A compound as claimed in claim 46 having the formula
wherein
R 1′ is hydrogen or C 1 -C 4 alkyl;
R 5 is hydrogen;
R 6 and R 6′ are hydrogen; and
R 7 and R 7′ are hydrogen;
or an N-oxide or salt thereof.
48 . A compound as claimed in claim 46 haying the formula
or the methyl ester thereof.
49 . A compound as claimed in claim 34 , wherein
A represents
X is N, CH, CF, CCl, or CBr;
R 1 is OR 1′ , wherein R 1′ is hydrogen or C 1 -C 4 alkyl;
R 2 is chlorine;
R 3 and R 4 are hydrogen;
R 5 is hydrogen, halogen, OH, amino, CN, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 alkylamino, or cyclopropyl;
R 6 and R 6′ are independently hydrogen, halogen, OH, NH 2 , CN, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, cyclopropyl, or vinyl; and
R 7 and R 7′ are independently hydrogen, halogen, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, cyclopropyl, C 1 -C 3 alkylamino, or phenyl;
or an N-oxide or salt thereof.
50 . A compound as claimed in claim 49 having the formula
wherein
R 1′ is hydrogen or C 1 -C 4 alkyl;
R 5 is hydrogen;
R 6 and R 6′ are hydrogen; and
R 7 and R 7′ are hydrogen;
or an N-oxide or salt thereof.
51 . A compound as claimed in claim 49 having the formula
or the methyl ester thereof.
52 . A compound as claimed in claim 34 , wherein
A represents
X is N, CH, CF, CCl, or CBr;
R 1 is OR 1′ , wherein R 1′ is hydrogen or C 1 -C 4 alkyl;
R 2 is chlorine;
R 3 and R 4 are hydrogen;
R 5 is hydrogen, halogen, OH, amino, CN, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 alkylamino, or cyclopropyl;
R 6 and R 6′ are independently hydrogen, halogen, OH, NH 2 , CN, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, cyclopropyl, or vinyl; and
R 7 and R 7′ are independently hydrogen, halogen, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, cyclopropyl, C 1 -C 3 alkylamino, or phenyl;
or an N-oxide or salt thereof.
53 . A compound as claimed in claim 52 having the formula
wherein
R 1′ is hydrogen or C 1 -C 4 alkyl;
R 5 is hydrogen;
R 6 is hydrogen or halogen;
R 6′ is hydrogen; and
R 7 and R 7′ are hydrogen;
or an N-oxide or salt thereof.
54 . A compound as claimed in claim 52 having the formula
or the methyl ester thereof.
55 . A compound as claimed in claim 52 having the formula
or the methyl ester thereof.Cited by (0)
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