IP Library › Granted Patent US 11,185,075

Granted Patent B2

US 11,185,075 · App. 16/469,877 · Granted Nov 30, 2021

Herbicidal phenyltriazolinones

Inventors: Tobias Seiser (Limburgerhof, DE); Manuel Johannes (Ludwigshafen, DE); Matthias Witschel (Ludwigshafen, DE); Liliana Parra Rapado (Limburgerhof, DE); Raphael Aponte (Limburgerhof, DE); Thomas Mietzner (Ludwigshafen, DE); Dario Massa (Limburgerhof, DE); Thomas Seitz (Ludwigshafen, DE); Peter Dombo (Limburgerhof, DE); Andreas Landes (Limburgerhof, DE); Stefan Tresch (Ludwigshafen, DE); Trevor William Newton (Limburgerhof, DE)

Assignee: BASF SE

A01N43/653 C07D249/12 C07D401/12

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Quick Facts

Patent No.: US 11,185,075
App. No.: 16/469,877
Granted: Nov 30, 2021
Kind: B2

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Abstract

The present invention relates to phenyltriazolinones of formula (I) or their agriculturally acceptable salts or derivatives, wherein the variables are defined according to the description, processes and intermediates for preparing the uracilpyryidines of the formula (I), compositions comprising them and their use as herbicides, i.e. for controlling harmful plants, and also a method for controlling unwanted vegetation which comprises allowing a herbicidal effective amount of at least one urycilpyridine of the formula (I) to act on plants, their seed and/or their habitat.

Claims (104)

1. A compound of formula (I)

wherein the variables have the following meanings:

R 1 is hydrogen, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl;

R 2 is hydrogen, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl;

R 3 is H or halogen;

R 4 is halogen, CN, NO 2 or NH 2 ;

R 5 is selected from the group consisting of H, halogen, CN, C 1 -C 3 -alkyl, C 1 -C 3 -haloalkyl, C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylthio, (C 1 -C 3 -alkyl)amino, di(C 1 -C 3 -alkyl)amino, C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, and C 1 -C 3 -alkoxycarbonyl;

R 6 is H, halogen, C 1 -C 3 -alkyl, C 1 -C 3 -alkoxy;

R 7 is OR 8 , SR 8 , NR 9 R 10 , NR 8 OR 8 , NR 8 S(O) 2 R 9 or NR 8 S(O) 2 NR 9 R 10 , wherein

R 8 is hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -haloalkenyl, C 3 -C 6 -haloalkynyl, C 1 -C 6 -cyanoalkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, di(C 1 -C 6 -alkoxy)C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, C 3 -C 6 -alkenyloxy-C 1 -C 6 -alkyl, C 3 -C 6 -haloalkenyloxy-C 1 -C 6 -alkyl, C 3 -C 6 -alkenyloxy-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 1 -C 6 -alkylcarbonyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxycarbonyl-C 1 -C 6 -alkyl, C 3 -C 6 -alkenyloxycarbonyl-C 1 -C 6 -alkyl, C 3 -C 6 -alkynyloxycarbonyl-C 1 -C 6 -alkyl, amino, (C 1 -C 6 -alkyl)amino, di(C 1 -C 6 -alkyl)amino, (C 1 -C 6 -alkylcarbonyl)amino, amino-C 1 -C 6 -alkyl, (C 1 -C 6 -alkyl)amino-C 1 -C 6 -alkyl, di(C 1 -C 6 -alkyl)amino-C 1 -C 6 -alkyl, aminocarbonyl-C 1 -C 6 -alkyl, (C 1 -C 6 -alkyl)aminocarbonyl-C 1 -C 6 -alkyl, di(C 1 -C 6 -alkyl)aminocarbonyl-C 1 -C 6 -alkyl,

—N═CR 11 R 12 , wherein R 11 and R 12 independently of one another are H, C 1 -C 4 -alkyl or phenyl;

C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 3 -C 6 -heterocyclyl, C 3 -C 6 -heterocyclyl-C 1 -C 6 -alkyl, phenyl, phenyl-C 1 -C 4 -alkyl or a 5- or 6 membered heteroaryl,

wherein each cycloalkyl, heterocyclyl, phenyl or heteroaryl ring can be substituted by one to four substituents selected from R 13 or a 3- to 7-membered carbocycle,

which carbocycle optionally has in addition to carbon atoms one or two ring members selected from the group consisting of

—N(R 11 )—, —N═N—, —C(═O)—, —O— and —S—, and

which carbocycle is optionally substituted with one to four substituents selected from R 13 ;

wherein R 13 is halogen, NO 2 , CN, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -alkoxycarbonyl;

R 9 , R 10 independently of one another are R 8 , or together form a 3- to 7-membered carbocycle,

which carbocycle optionally has in addition to carbon atoms one or two ring members selected from the group consisting of —N(R 11 )—, —N═N—, —C(═O)—, —O— and —S—, and

which carbocycle is optionally substituted with one to four substituents selected from R 13 ;

n is 1 to 3;

Q is O, S, SO, SO 2 , NH or (C 1 -C 3 -alkyl)N;

W is O or S;

X is O or S;

Y is O or S

Z is phenyl, pyridyl, pyridazinyl, pyrimidinyl or pyrazinyl,

each of which is attached to X and Q via vicinal carbon atoms, and

each of which is optionally substituted by 1 to 4 substituents selected from the group consisting of halogen, CN, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy;

or an agriculturally acceptable salt, ester, amide or thioester thereof.

2. The compound of formula (I) or an agriculturally acceptable salt, ester, amide or thioester thereof of claim 1 , wherein R 1 is C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl, R 2 is C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl, and Y is O.

3. The compound of formula (I) or an agriculturally acceptable salt, ester, amide or thioester thereof of claim 1 , wherein R 3 is H, F or Cl, and R 4 is F, Cl or CN.

4. The compound of formula (I) or an agriculturally acceptable salt, ester, amide or thioester thereof of claim 1 , wherein R 5 is H, C 1 -C 3 -alkyl or C 1 -C 3 -alkoxy, and R 6 is H.

5. The compound of formula (I) or an agriculturally acceptable salt, ester, amide or thioester thereof of claim 1 , wherein R 7 is OR 8 , NR 8 S(O) 2 R 9 or NR 8 S(O) 2 NR 9 R 10 , wherein

R 8 is hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, di(C 1 -C 6 -alkoxy)C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkyl or C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl; and

R 9 , R 10 are C 1 -C 6 -alkyl.

6. The compound of formula (I) or an agriculturally acceptable salt, ester, amide or thioester thereof of claim 1 , wherein n is 1.

7. The compound of formula (I) or an agriculturally acceptable salt, ester, amide or thioester thereof of claim 1 , wherein Q, W and X and Y are O.

8. The compound of formula (I) or an agriculturally acceptable salt, ester, amide or thioester thereof of claim 1 , wherein Z is phenyl or pyridyl, each of which is attached to X and Q via vicinal carbon atoms, and each of which is optionally substituted by 1 to 4 substituents selected from the group consisting of halogen, CN, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy and C 1 -C 6 -haloalkoxy.

9. A herbicidal composition comprising an herbicidally active amount of the compound of formula (I) or an agriculturally acceptable salt, ester, amide or thioester thereof of claim 1 and at least one inert liquid and/or solid carrier and, optionally, at least one surface-active substance.

10. A process for the preparation of herbicidal active compositions, comprising mixing an herbicidally active amount of the compound of formula (I) or an agriculturally acceptable salt, ester, amide or thioester thereof of claim 1 and at least one inert liquid and/or solid carrier and, optionally, at least one surface-active substance.

11. A method of controlling undesired vegetation, which comprises allowing an herbicidally active amount of the compound of formula (I) or an agriculturally acceptable salt, ester, amide or thioester thereof of claim 1 to act on plants, their environment or on seed.

12. The method of claim 11 , wherein R 1 is C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl, R 2 is C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl, and Y is O.

13. The method of claim 11 , wherein R 3 is H, F or Cl, and R 4 is F, Cl or CN.

14. The method of claim 11 , wherein R 5 is H, C 1 -C 3 -alkyl or C 1 -C 3 -alkoxy, and R 6 is H.

15. The method of claim 11 , wherein R 7 is OR 8 , NR 8 S(O) 2 R 9 or NR 8 S(O) 2 NR 9 R 10 , wherein

R 9 , R 10 are C 1 -C 6 -alkyl.

16. The method of claim 11 , wherein n is 1.

17. The method of claim 11 , wherein Q, W and X and Y are O.

18. The method of claim 11 , wherein Z is phenyl or pyridyl, each of which is attached to X and Q via vicinal carbon atoms, and each of which is optionally substituted by 1 to 4 substituents selected from the group consisting of halogen, CN, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy and C 1 -C 6 -haloalkoxy.

19. A herbicidal composition comprising a herbicidally active amount of the compound of formula (I) or an agriculturally acceptable salt, ester, amide or thioester thereof of claim 1 , and at least one further active compound selected from

B) herbicides of class b1) to b15):

b1) lipid biosynthesis inhibitors;

b2) acetolactate synthase inhibitors (ALS inhibitors);

b3) photosynthesis inhibitors;

b4) protoporphyrinogen-IX oxidase inhibitors,

b5) bleacher herbicides;

b6) enolpyruvyl shikimate 3-phosphate synthase inhibitors (EPSP inhibitors);

b7) glutamine synthetase inhibitors;

b8) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors);

b9) mitosis inhibitors;

b10) inhibitors of the synthesis of very long chain fatty acids (VLCFA inhibitors);

b11) cellulose biosynthesis inhibitors;

b12) decoupler herbicides;

b13) auxinic herbicides;

b14) auxin transport inhibitors; and

b15) other herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, indaziflam, maleic hydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, triaziflam, tridiphane and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (CAS 499223-49-3) and its salts and esters;

including their agriculturally acceptable salts, amides, esters, and thioesters, provided they have an acid group;

and

C) safeners selected from the group consisting of quinolin-8-oxy)acetic acids, 1-phenyl-5-haloalkyl-1H-1,2,4-triazol-3-carboxylic acids, 1-phenyl-4,5-dihydro-5-alkyl-1H-pyrazol-3,5-dicarboxylic acids, 4,5-dihydro-5,5-diaryl-3-isoxazol carboxylic acids, dichloroacetamides, alpha-oximinophenylacetonitriles, acetophenonoximes, 4,6-dihalo-2-phenylpyrimidines, N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2-benzoic amides, 1,8-naphthalic anhydride, 2-halo-4-(haloalkyl)-5-thiazol carboxylic acids, phosphorthiolates and N-alkyl-O-phenylcarbamates,

including their agriculturally acceptable salts, amides, esters, and thioesters, provided they have an acid group.

20. A process for preparing a compound of formula (I)