Herbicidally and insecticidally active thiazolopyridinones
View Patent ↗Thiazolopyridinones of the general formula (I) are described as herbicides. In this formula (I), R 1 , R 2 , R 3 and R 4 represent radicals such as hydrogen, organic radicals such as alkyl and other radicals such as halogen, nitro and cyano.
1. A thiazolopyridinone of formula (I) and/or a salt thereof
in which
R 1 represents hydrogen, halogen, nitro, cyano,
(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkylthio, (C 1 -C 6 )-alkylsulfinyl, (C 1 -C 6 )-alkylsulfonyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, di-(C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl or (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-alkyl, each of which is substituted by n halogen atoms,
R 2 represents hydrogen,
(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 3 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl or di-(C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylsulfinyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylsulfonyl-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, cyano-(C 1 -C 6 )-alkyl, each of which is substituted by n halogen atoms, or phenyl or benzyl, each of which is substituted by n radicals from the group consisting of halogen, (C 1 -C 6 )-alkyl and (C 1 -C 6 )-alkoxy,
R 3 represents hydroxy, O—C(═O)R 7 , O—C(=L)MR 8 , O—SO 2 R 9 , O—P(=L)R 10 R 11 , O—C(=L)NR 12 R 13 , O-E or O—R 14 ,
R 4 represents R 4a or R 4b ,
R 4a represents aryl which is substituted by n radicals R 5 and one radical R 6 ,
R 4b represents 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, 1,2,4-triazol-1-yl, 1,2,4-triazol-3-yl, 1,2,4-triazol-4-yl, 1,2,4-triazol-5-yl, 1,2,3-triazol-1-yl, 1,2,3-triazol-2-yl, 1,2,3-triazol-4-yl, tetrazol-1-yl, tetrazol-2-yl, tetrazol-5-yl, indol-1-yl, indol-2-yl, indol-3-yl, isoindol-1-yl, isoindol-2-yl, benzofur-2-yl, benzothiophen-2-yl, benzofur-3-yl, benzothiophen-3-yl, benzoxazol-2-yl, benzothiazol-2-yl, benzimidazol-2-yl, indazol-1-yl, indazol-2-yl, indazol-3-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl or 1,2,4-triazin-6-yl, substituted by n radicals R 5 and by m radicals R 6 ,
R 5 represents hydrogen, halogen, nitro, cyano,
(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkylthio, (C 1 -C 6 )-alkylsulfinyl, (C 1 -C 6 )-alkylsulfonyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl or (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-alkyl, each of which is substituted by n halogen atoms,
R 6 represents aryl or heteroaryl, each of which is substituted by s radicals R 5 ,
E represents a metal ion equivalent or an ammonium ion,
L represents oxygen or sulfur,
M represents oxygen or sulfur,
R 7 represents (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, di-(C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl or (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-alkyl, each of which is substituted by n halogen atoms,
a fully saturated 3- to 6-membered ring consisting of 3 to 5 carbon atoms and 1 to 3 heteroatoms from the group consisting of oxygen, sulfur and nitrogen, which ring is substituted by n radicals from the group consisting of halogen, (C 1 -C 6 )-alkyl and (C 1 -C 6 )-alkoxy,
or (C 3 -C 6 )-cycloalkyl, phenyl, phenyl-(C 1 -C 6 )-alkyl, phenoxy-(C 1 -C 6 )-alkyl or heteroaryloxy-(C 1 -C 6 )-alkyl, each of which is substituted by n radicals from the group consisting of halogen, (C 1 -C 6 )-alkyl and (C 1 -C 6 )-alkoxy,
R 8 represents (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl or di-(C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, each of which is substituted by n halogen atoms, or (C 3 -C 6 )-cycloalkyl, phenyl or benzyl, each of which is substituted by n radicals from the group consisting of halogen, (C 1 -C 6 )-alkyl and (C 1 -C 6 )-alkoxy,
R 9 , R 10 , R 11 independently of one another represent (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, N—(C 1 -C 6 )-alkylamino, N,N-di-(C 1 -C 6 )-alkylamino, (C 1 -C 6 )-alkylthio, (C 2 -C 6 )-alkenyl or (C 3 -C 6 )-cycloalkylthio, each of which is substituted by n halogen atoms,
or phenyl, benzyl, phenoxy or phenylthio, each of which is substituted by n radicals from the group consisting of halogen, (C 1 -C 6 )-alkyl and (C 1 -C 6 )-alkoxy,
R 12 , R 13 independently of one another each represent hydrogen,
(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 6 )-alkenyl, (C 1 -C 6 )-alkoxy or (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, substituted by n halogen atoms,
phenyl or benzyl, each of which is substituted by n radicals from the group consisting of halogen, (C 1 -C 6 )-alkyl and (C 1 -C 6 )-alkoxy,
or R 12 and R 13 together with the nitrogen atom to which they are attached form a 3- to 6-membered ring containing 2 to 5 carbon atoms and in each case 0 or 1 oxygen or sulfur atoms,
R 14 represents (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-alkyl or di-(C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, each of which is substituted by n halogen atoms,
(C 3 -C 6 )-cycloalkyl substituted by n radicals from the group consisting of halogen, (C 1 -C 6 )-alkyl and (C 1 -C 6 )-alkoxy,
a fully saturated 3- to 6-membered ring consisting of 3 to 5 carbon atoms and 1 to 3 heteroatoms from the group consisting of oxygen, sulfur and nitrogen, which ring is substituted by n radicals from the group consisting of halogen, (C 1 -C 6 )-alkyl and (C 1 -C 6 )-alkoxy,
phenyl, phenyl-(C 1 -C 6 )-alkyl, heteroaryl, phenoxy-(C 1 -C 6 )-alkyl or heteroaryloxy-(C 1 -C 6 )-alkyl, substituted by n radicals from the group consisting of halogen, (C 1 -C 6 )-alkyl and (C 1 -C 6 )-alkoxy,
m represents 0 or 1,
n represents 0, 1, 2 or 3,
s represents 0, 1, 2, 3 or 4.
2. The thiazolopyridinone as claimed in claim 1 in which
R 1 represents hydrogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkylthio, (C 1 -C 6 )-alkylsulfonyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl or (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-alkyl, each of which is substituted by n halogen atoms,
R 2 represents hydrogen,
(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 3 -CO-alkynyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, cyano-(C 1 -C 6 )-alkyl, each of which is substituted by n halogen atoms,
or phenyl or benzyl, each of which is substituted by n radicals from the group consisting of halogen, (C 1 -C 6 )-alkyl and (C 1 -C 6 )-alkoxy,
R 3 represents hydroxy, O—C(═O)R 7 , O—C(=L)MR 8 , O—SO 2 R 9 , O—P(=L)R 10 R 11 , O—C(=L)NR 12 R 13 , O-E or O—R 14 ,
R 4 represents R 4a or R 4b ,
R 4a represents phenyl which is substituted by one, two or three radicals R 5 and one radical R 6 ,
R 4b represents 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, 1,2,4-triazol-1-yl, 1,2,4-triazol-3-yl, 1,2,4-triazol-4-yl, 1,2,4-triazol-5-yl, 1,2,3-triazol-1-yl, 1,2,3-triazol-2-yl, 1,2,3-triazol-4-yl, tetrazol-1-yl, tetrazol-2-yl, tetrazol-5-yl, indol-1-yl, indol-2-yl, indol-3-yl, isoindol-1-yl, isoindol-2-yl, benzofur-2-yl, benzothiophen-2-yl, benzofur-3-yl, benzothiophen-3-yl, benzoxazol-2-yl, benzothiazol-2-yl, benzimidazol-2-yl, indazol-1-yl, indazol-2-yl, indazol-3-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl or 1,2,4-triazin-6-yl, substituted by one or two radicals R 5 and by m radicals R 6 ,
R 5 represents hydrogen, halogen,
(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 1 -C 6 )-alkoxy, (C 3 -C 6 )-cycloalkyl or (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, each of which is substituted by n halogen atoms,
R 6 represents phenyl substituted by n radicals R 5 or heteroaryl substituted by one, two or three radicals R 5 ,
E represents a metal ion equivalent or an ammonium ion,
L represents oxygen or sulfur,
M represents oxygen or sulfur,
R 7 represents (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, di-(C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl or (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-alkyl, each of which is substituted by n halogen atoms,
a fully saturated 3- to 6-membered ring consisting of 3 to 5 carbon atoms and 1 to 3 heteroatoms from the group consisting of oxygen, sulfur and nitrogen, which ring is substituted by n radicals from the group consisting of halogen, (C 1 -C 6 )-alkyl and (C 1 -C 6 )-alkoxy,
or (C 3 -C 6 )-cycloalkyl, phenyl, phenyl-(C 1 -C 6 )-alkyl, phenoxy-(C 1 -C 6 )-alkyl or heteroaryloxy-(C 1 -C 6 )-alkyl, each of which is substituted by n radicals from the group consisting of halogen, (C 1 -C 6 )-alkyl and (C 1 -C 6 )-alkoxy,
R 8 represents (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl or di-(C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, each of which is substituted by n halogen atoms,
or (C 3 -C 6 )-cycloalkyl, phenyl or benzyl, each of which is substituted by n radicals from the group consisting of halogen, (C 1 -C 6 )-alkyl and (C 1 -C 6 )-alkoxy,
R 9 , R 10 , R 11 independently of one another represent (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, N—(C 1 -C 6 )-alkylamino, N,N-di-(C 1 -C 6 )-alkylamino, (C 1 -C 6 )-alkylthio, (C 2 -C 6 )-alkenyl or (C 3 -C 6 )-cycloalkylthio, each of which is substituted by n halogen atoms,
or phenyl, benzyl, phenoxy or phenylthio, each of which is substituted by n radicals from the group consisting of halogen, (C 1 -C 6 )-alkyl and (C 1 -C 6 )-alkoxy,
R 12 , R 13 independently of one another each represent hydrogen,
(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 6 )-alkenyl, (C 1 -C 6 )-alkoxy or (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, substituted by n halogen atoms,
phenyl or benzyl, each of which is substituted by n radicals from the group consisting of halogen, (C 1 -C 6 )-alkyl and (C 1 -C 6 )-alkoxy,
or R 12 and R 13 together with the nitrogen atom to which they are attached form a 3- to 6-membered ring containing 2 to 5 carbon atoms and in each case 0 or 1 oxygen or sulfur atoms,
R 14 represents (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-alkyl or di-(C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, each of which is substituted by n halogen atoms,
(C 3 -C 6 )-cycloalkyl substituted by n radicals from the group consisting of halogen, (C 1 -C 6 )-alkyl and (C 1 -C 6 )-alkoxy,
a fully saturated 3- to 6-membered ring consisting of 3 to 5 carbon atoms and 1 to 3 heteroatoms from the group consisting of oxygen, sulfur and nitrogen, which ring is substituted by n radicals from the group consisting of halogen, (C 1 -C 6 )-alkyl and (C 1 -C 6 )-alkoxy,
phenyl, phenyl-(C 1 -C 6 )-alkyl, heteroaryl, phenoxy-(C 1 -C 6 )-alkyl or heteroaryloxy-(C 1 -C 6 )-alkyl, substituted by n radicals from the group consisting of halogen, (C 1 -C 6 )-alkyl and (C 1 -C 6 )-alkoxy,
m represents 0 or 1,
n represents 0, 1, 2 or 3,
s represents 0, 1, 2, 3 or 4.
3. A herbicidal composition, comprising a herbicidally active content of at least one compound of the formula (I) as claimed in claim 1 .
4. The herbicidal composition as claimed in claim 3 in a mixture with formulation auxiliaries.
5. The herbicidal composition as claimed in claim 3 , comprising at least one further pesticidally active substance selected from the group consisting of insecticides, acaricides, herbicides, fungicides, safeners and growth regulators.
6. The herbicidal composition as claimed in claim 5 , comprising a safener.
7. The herbicidal composition as claimed in claim 6 , comprising cyprosulfamide, cloquintocet-mexyl, mefenpyr-diethyl or isoxadifen-ethyl.
8. The herbicidal composition as claimed in claim 5 , comprising a further herbicide.
9. A method for controlling unwanted plants, comprising applying an effective amount of at least one compound of formula (I) as claimed in claim 1 to plants and/or to a site of unwanted plant growth.
10. A compound of formula (I) as claimed in claim 1 capable of being used for controlling unwanted plants.
11. The compound as claimed in claim 10 , wherein the compound of formula (I) is capable of being used for controlling unwanted plants in crops of useful plants.
12. The compound as claimed in claim 11 , wherein the useful plants are transgenic useful plants.
13. An insecticidal composition, comprising an insecticidally effective amount of at least one compound of formula (I) as claimed in claim 1 .
14. The insecticidal composition as claimed in claim 13 in a mixture with one or more formulation auxiliaries.
15. The insecticidal composition as claimed in claim 13 , comprising at least one further pesticidally active substance selected from the group consisting of insecticides, acaricides, herbicides, fungicides, safeners and growth regulators.
16. A method for controlling unwanted insects, comprising applying an effective amount of at least one compound of formula (I) as claimed in claim 1 to one or more plants and/or to one or more insects.
17. A compound of formula (I) as claimed in claim 1 capable of being used for controlling unwanted insects.