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US-12617803-B2 - Condensed isoxazoline derivatives and their use as herbicides

US12617803B2US 12617803 B2US12617803 B2US 12617803B2US-12617803-B2

Abstract

The invention relates to compounds of formula (I), and their use as herbicides. In said formula, R 1 to R 6 represent groups such as hydrogen, halo-gen or organic groups such as alkyl, alkenyl, alkynyl, or alkoxy; W is a bicyclic heterocycle; X is a bond or a divalent unit; Y is hydrogen, cyano, hydroxyl or a linear or cyclic organic group. The invention further refers to a composition comprising such compound and to the use thereof for controlling unwanted vegetation.

Inventors

  • Gunther Zimmermann
  • Markus Kordes
  • Gerd Kraemer
  • Tobias SEISER
  • Thomas Seitz
  • Ulrike Anders
  • Giuseppe Allegretta
  • Jens Lerchl

Assignees

  • BASF SE

Dates

Publication Date
20260505
Application Date
20210426
Priority Date
20200505

Claims (13)

  1. 1 . A compound of formula (I) wherein the substituents have the following meanings: R 1 is hydrogen, (C 1 -C 3 )-alkyl, (C 3 -C 4 )-cycloalkyl, (C 1 -C 3 )-haloalkyl, (C 2 -C 3 )-alkenyl, (C 2 -C 3 )-alkynyl, (C 1 -C 3 )-alkoxy-(C 1 -C 3 )-alkyl, (C 1 -C 3 )-alkoxy, or (C 1 -C 3 )-haloalkoxy; R 2 is hydrogen; R 3 is halogen, cyano, or (C 1 -C 3 )-alkyl; R 4 is hydrogen or fluorine; R 5 is halogen, cyano, or (C 1 -C 3 )-alkyl; R 6 is hydrogen; W is a divalent unit selected from the group consisting of (W 1 ), (W 2 ), (W 3 ), (W 6 ), (W 7 ), (W 16 ), and (W 18 ), and wherein the divalent unit is substituted by m radicals from the group consisting of R k and R l , and where carbon atoms bear n oxo groups, and wherein the left arrow represents the bond to the adjacent phenyl ring and the right arrow represents the bond to the adjacent carbonyl group: X is a bond (X 0 ); Y is Z; Z is a three-, four-, five- or six-membered saturated, partly unsaturated, fully unsaturated or aromatic ring, except phenyl, which is formed from r carbon atoms, n nitrogen atoms, n sulfur atoms, and n oxygen atoms, and which is substituted by m radicals from the group consisting of CO 2 R e , CONR b R h , R b , R c , R e and R f , and where the sulfur atoms and carbon atoms bear n oxo groups; R a is (C 1 -C 6 )-alkyl or (C 3 -C 6 )-cycloalkyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, and hydroxy; R b is hydrogen, (C 1 -C 3 )-alkoxy, or (C 3 -C 6 )-cycloalkyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, and hydroxy; R c is fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) n R a or (C 1 -C 6 )-alkoxy, (C 3 -C 6 )-alkenyloxy or (C 3 -C 6 )-alkynyloxy, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, and (C 1 -C 2 )-alkoxy; R d is hydrogen or (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 4 )-alkenyl, or (C 2 -C 4 )-alkynyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, and (C 1 -C 2 )-alkoxy; R e is hydrogen or (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 4 )-alkenyl, phenyl-(C 1 -C 3 )-alkyl, or (C 2 -C 4 )-alkynyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, and (C 1 -C 2 )-alkoxy; R f is (C 1 -C 3 )-alkyl or (C 1 -C 3 )-alkoxy; R h is hydrogen or (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 4 )-alkenyl, (C 1 -C 6 )-alkoxycarbonyl-(C 1 -C 6 )-alkyl, or (C 2 -C 4 )-alkynyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, and (C 1 -C 2 )-alkoxy; R k is (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-alkynyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, hydroxyl and (C 1 -C 2 )-alkoxy; R l is fluorine, chlorine, bromine, iodine, cyano, hydroxyl or (C 1 -C 6 )-alkoxy, (C 3 -C 6 )-alkenyloxy, (C 3 -C 6 )-alkynyloxy, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, and hydroxyl; m is 0, 1, 2, 3, 4, or 5; n is 0, 1, or 2; r is 1, 2, 3, 4, 5, or 6; including their agriculturally acceptable salts.
  2. 2 . The compound as claimed in claim 1 , wherein the substituents have the following meaning: R 1 is hydrogen.
  3. 3 . The compound as claimed in claim 1 , wherein the substituents have the following meaning: R 3 fluorine or chlorine.
  4. 4 . The compound as claimed in claim 1 , wherein the substituents have the following meaning: R 4 is hydrogen.
  5. 5 . The compound as claimed in claim 1 , wherein the substituents have the following meaning: W is a divalent unit selected from the group consisting of (W 2 ), (W 3 ), (W 7 ), (W 16 ), and (W 18 ):
  6. 6 . The compound as claimed in claim 1 , wherein the substituents have the following meaning: Y is Z; Z is a four- or five-membered saturated or partly unsaturated ring, which is formed from r carbon atoms and n oxygen atoms, each substituted by m radicals from the group consisting of CO 2 R e , CONR b R h , CONR e SO 2 R a , R b , R c , R e , and R f .
  7. 7 . The compound as claimed in claim 1 , wherein the substituents have the following meaning: R 1 is hydrogen; R 2 is hydrogen; R 3 is halogen; R 4 is hydrogen; R 5 is halogen; R 6 is hydrogen; W is a divalent unit selected from the group consisting of (W 1 ), (W 2 ), (W 3 ), (W 6 ), (W 7 ), (W 16 ), and (W 18 ), and wherein the divalent unit is substituted by m radicals from the group consisting of R k and R l , and where carbon atoms bear n oxo groups: X is a bond; Y is Z; Z is a three-, four-, five-, or six-membered saturated, partly unsaturated, fully unsaturated, or aromatic ring, except phenyl, which is formed from r carbon atoms, n nitrogen atoms, n sulfur atoms, and n oxygen atoms, and which is substituted by m radicals selected from the group consisting of CO 2 R e , CONR b R h , R b , R c , R e , and R f , and where the sulfur atoms and carbon atoms bear n oxo group; R a is (C 1 -C 6 )-alkyl or (C 3 -C 6 )-cycloalkyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, and hydroxy; R b is hydrogen, or (C 1 -C 6 )-alkyl or (C 3 -C 6 )-cycloalkyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, and hydroxy; R c is fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) n R a or (C 1 -C 6 )-alkoxy, (C 3 -C 6 )-alkenyloxy or (C 3 -C 6 )-alkynyloxy, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, and (C 1 -C 2 )-alkoxy; R e is hydrogen or (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 4 )-alkenyl, phenyl-(C 1 -C 3 )-alkyl or (C 2 -C 4 )-alkynyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, and (C 1 -C 2 )-alkoxy; R f is (C 1 -C 3 )-alkyl or (C 1 -C 3 )-alkoxy; R h is hydrogen or (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 4 )-alkenyl, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-alkyl, or (C 2 -C 4 )-alkynyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, and (C 1 -C 2 )-alkoxy; R k is (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-alkynyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, hydroxyl, and (C 1 -C 2 )-alkoxy; R l is fluorine, chlorine, bromine, iodine, cyano, hydroxyl or (C 1 -C 6 )-alkoxy, (C 3 -C 6 )-alkenyloxy, (C 3 -C 6 )-alkynyloxy, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, and hydroxyl; m is 0, 1, 2, 3, 4, 5, or 6; n is 0, 1, or 2; r is 1, 2, 3, 4, or 5.
  8. 8 . The compound as claimed in claim 1 , wherein the substituents have the following meanings: R 1 is hydrogen, (C 1 -C 3 )-alkyl, or (C 3 -C 4 )-cycloalkyl.
  9. 9 . The compound as claimed in claim 1 , wherein the substituents have the following meanings: R 5 is fluorine or chlorine.
  10. 10 . A composition comprising at least one compound as claimed in claim 1 , and at least one auxiliary, which is customary for formulating crop protection compounds.
  11. 11 . The composition as claimed in claim 10 , comprising a further herbicide.
  12. 12 . A method for controlling unwanted vegetation comprising applying an herbicidally effective amount of at least one compound as claimed in claim 1 to unwanted vegetation, their seed, and/or their habitat.
  13. 13 . A compound having a formula wherein the substituents have the following meanings: R 1 is hydrogen; R 2 is hydrogen; R 3 is halogen; R 4 is hydrogen; R 5 is halogen; R 6 is hydrogen; W is a divalent unit selected from the group consisting of (W 1 ), (W 2 ), (W 3 ), (W 6 ), (W 7 ), (W), (W 12 ), (W 16 ), (W 18 ), (W 20 ), (W 21 ), (W 22 ), (W 23 ), and (W 24 ), and wherein the divalent unit is substituted by m radicals from the group consisting of R k , wherein the left arrow represents the bond to the adjacent phenyl ring and the right arrow represents the bond to the adjacent carbonyl group: X is a bond; Y is Z or (C 1 -C 8 )-alkyl, which is substituted by m radicals from the group consisting of CO 2 R e ; Z is cyclopentyl, cyclopentenyl, or tetrahydrofuranyl, each substituted by m radicals from the group consisting of CO 2 R e ; R e is hydrogen or (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 4 )-alkenyl, phenyl-(C 1 -C 3 )-alkyl or (C 2 -C 4 )-alkynyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, CO 2 R a and (C 1 -C 2 )-alkoxy, (C 1 -C 3 )-alkylthio, (C 1 -C 3 )-alkylsulfinyl, (C 1 -C 3 )-alkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl; R k is (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-alkynyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, hydroxyl, and (C 1 -C 2 )-alkoxy; m is 0, 1, or 2; including agriculturally acceptable salts thereof.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS This is the U.S. national phase of International Application No. PCT/EP2021/060787, filed Apr. 26, 2021, which claims the benefit of European Patent Application No. 20172950.6, filed on May 5, 2020. The present invention relates to Bicyclic Heterocycle compounds and compositions comprising the same. The invention also relates to the use of the Bicyclic Heterocycle compounds or the corresponding compositions for controlling unwanted vegetation. Furthermore, the invention relates to methods of applying the Bicyclic Heterocycle compounds or the corresponding compositions. For the purpose of controlling unwanted vegetation, especially in crops, there is an ongoing need for new herbicides that have high activity and selectivity together with a substantial lack of toxicity for humans and animals. WO12130798, WO1404882, WO14048882, WO18228985, WO18228986, WO19034602, and WO19145245 describe 3-phenylisoxazoline-5-carboxamides and their use as herbicides. The compounds of the prior art often suffer from insufficient herbicidal activity, in particular at low application rates, and/or unsatisfactory selectivity resulting in a low compatibility with crop plants. Accordingly, it is an object of the present invention to provide compounds having a strong herbicidal activity, in particular even at low application rates, a sufficiently low toxicity for humans and animals and/or a high compatibility with crop plants. The Bicyclic Heterocycle compounds should also show a broad activity spectrum against a large number of different unwanted plants. These and further objectives are achieved by the compounds of formula (I) defined below including their agriculturally acceptable salts, amides, esters or thioesters. Accordingly, the present invention provides compounds of formula (I) wherein the substituents have the following meanings: R1 hydrogen, (C1-C3)-alkyl, (C3-C4)-cycloalkyl, (C1-C3)-haloalkyl, (C2-C3)-alkenyl, (C2-C3)-haloalkenyl, (C2-C3)-alkynyl, (C2-C3)-haloalkynyl, (C1-C3)-alkoxy-(C1-C3)-alkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy;R2 hydrogen, halogen, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy;R3 hydrogen, halogen, nitro, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, hydroxy-(C1-C3)-alkyl, (C3-C5)-cycloalkyl, (C3-C5)-halocycloalkyl, hydroxy-(C3-C5)-cycloalkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy, (C1-C3)-alkoxycarbonyl, (C2-C3)-alkenyl, (C2-C3)-haloalkenyl, (C2-C3)-alkynyl, (C2-C3)-haloalkynyl, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl;R4 hydrogen, halogen, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C3-C4)-halocycloalkyl, (C1-C3)-haloalkoxy, (C2-C3)-haloalkenyl, (C2-C3)-haloalkynyl;R5 hydrogen, halogen, nitro, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, hydroxy-(C1-C3)-alkyl, (C3-C5)-cycloalkyl, (C3-C5)-halocycloalkyl, hydroxy-(C3-C5)-cycloalkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy, (C1-C3)-alkoxycarbonyl, (C2-C3)-alkenyl, (C2-C3)-haloalkenyl, (C2-C3)-alkynyl, (C2-C3)-haloalkynyl, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl;R6 hydrogen, halogen, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy;W a divalent unit selected from the group consisting of (W1) to (W24), and wherein the divalent unit is substituted by m radicals from the group consisting of Rk and Rl, and where carbon atoms bear n oxo groups: X a bond (X0) or a divalent unit from the group consisting of (X1), (X2), (X3), (X4), (X5), and (X6): R7-R12 each independently hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, CO2Re, CONRbRd, Ra, or (C1-C6)-alkyl, (C3-C5)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano, or (C1-C6)-alkoxy, (C3-C6)-cycloalkoxy, (C3-C6)-alkenyloxy or (C3-C6)-alkynyloxy, each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano and (C1-C2)-alkoxy;Y hydrogen, cyano, hydroxyl, Z, or(C1-C12)-alkyl, (C3-C8)-cycloalkyl, (C2-C12)-alkenyl or (C2-C12)-alkynyl, each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, ORd, Z, OZ, NHZ, S(O)nRa, SO2NRbRd, SO2NRbCORe, CO2Re, CONRbRh, CORb, CONReSO2Ra, NRbRe, NRbCORe, NRbCONReRe, NRbCO2Re, NRbSO2Re NRbSO2NRbRe, OCONRbRe, OCSNRbRe, PORfRf and C(Rb)═NORe; Z a three-, four-, five- or six-membered saturated, partly unsaturated, fully unsaturated or aromatic ring, except phenyl, which is formed from r carbon atoms, n nitrogen atoms, n sulfur atoms and n oxygen atoms, and which is substituted by m radicals from the group consisting of CO2Re, CONRbRh, S(O)nRa, SO2NRbRd, SO2NRbCORe, CORb, CONReSO2Ra, NRbRe, NRbCORe, NRbCONReRe, NRbCO2Re, NRbSO2Re, NRbSO2NRbRe, OCONRbRe, OCSNRbRe, PORfRf and C(Rb)═NORe, Rb, Rc, Re and Rf, and where the sulfur atoms and carbon atoms bear n oxo groups;Ra (C1-C6)-alkyl or (C3-C6)-cycloalkyl, each of