# US 2019/0166838 A1 · Method for controlling ppo resistant weeds

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- Number: US 2019/0166838 A1
- Document ID: US20190166838A1
- Status: Published application
- Kind: A1
- Application number: 16/321,237
- Filed: 2017-07-25
- Published: 2019-06-06
- Earliest claimed: 2016-07-29
- Assignees: BASF SE
- Applicants: BASF SE
- Inventors: Gregory ARMEL; Cyrill ZAGAR; Andreas LANDES; Tobias SEISER
- Web page: https://patentgrep.com/patent/US20190166838A1

## CPC

- A01N 43/54: 1,3-Diazines; Hydrogenated 1,3-diazines
- C07D 239/54: as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- A01N 41/10: Sulfones; Sulfoxides
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

A method for controlling PPO resistant weeds, wherein compounds of formula (I) wherein the variables are defined as given in the description and claims; are applied to the PPO inhibitor herbicide resistant weed, parts of it or its propagation material.

## Claims

### Claim at position 1

1-15. (canceled)

### Claim at position 2

16: A method for controlling the growth of PPO resistant weeds, which comprises contacting such weeds, parts of it, its propagation material or its habitat with compounds of formula (I)
wherein
R1 is H, F or Cl;
R2 is F, Cl, Br, CN, C(O)NH2 or C(S)NH;
R3 is H, F, Cl, CH3 or OCH3;
R4 is H, CN, CH3, CF3, OCH3, OC2H5, SCH3, SC2H5, (CO)OC2H5 or CH2R6,
wherein R6 is F, Cl, OCH3, SCH3, SC2H5, CH2F, CH2Br or CH2OH;
R5 is (C1-C6-alkyl)amino, (C1-C6-dialkyl)amino, (NH)OR7, OH, OR8 or SR8,
wherein R7 is CH3, C2H5 or phenyl; and
R8 is C1-C6-alkyl, C2-C6-alkenyl, C3-C6-alkynyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkoxy-C1-C6-alkyl, C2-C6-cyanoalkyl, C1-C4-alkoxy-carbonyl-C1-C4-alkyl, C1-C4-alkyl-carbonyl-amino, C1-C6-alkylsulfinyl-C1-C6-alkyl, C1-C6-alkyl-sulfonyl-C1-C6-alkyl, C1-C6-dialkoxy-C1-C6-alkyl, C1-C6-alkyl-carbonyloxy-C1-C6-alkyl, phenyl-carbonyl-C1-C6-alkyl, tri(C1-C3-alkyl)-silyl-C1-C6-alkyl, tri(C1-C3-alkyl)-silyl-C2-C6-alkenyl, tri(C1-C3-alkyl)-silyl-C2-C6-alkynyl, tri(C1-C3-alkyl)-silyl-C1-C6-alkoxy-C1-C6-alkyl, dimethylamino, tetrahydropyranyl, tetrahydrofuranyl-C1-C3-alkyl, phenyl-C1-C6-alkoxy-C1-C6-alkyl, phenyl-C1-C3-alkyl, pyridyl-C1-C3-alkyl, pyridyl or phenyl,
wherein the pyridyl and phenyl rings independently of one another are substituted by one to five substituents selected from the group consisting of halogen, C1-C3-alkyl or C1-C2-haloalkyl;
C3-C6-cycloalkyl or C3-C6-cycloalkyl-C1-C4-alkyl,
wherein the cycloalkyl rings independently of one another are unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C3-alkyl and C1-C2-haloalkyl;
X is O, S, S(O) or S(O)2;
Y is N or CH; and
Z is O, S, S(O) or S(O)2;
wherein the PPO resistant weeds are weeds, that are resistant to PPO-inhibiting herbicides except the compounds of formula (I).

### Claim at position 3 (depends on 16)

17: The method of claim 16, wherein the PPO resistant weeds are resistant to at least one PPO-inhibiting herbicide selected from azafenidin and flumioxazin.

### Claim at position 4 (depends on 16)

18: The method of claim 16, wherein the PPO resistant weeds are resistant to at least one PPO-inhibiting herbicide selected from fomesafen and lactofen.

### Claim at position 5 (depends on 16)

19: The method of claim 16, wherein the PPO resistant weeds are not controlled by the application rate of 200 g/ha or lower of at least one PPO-inhibiting herbicide except the compound of formula (I).

### Claim at position 6 (depends on 16)

20: The method of claim 16, wherein the PPO resistant weeds are selected from the group consisting of Acalypha ssp., Amaranthus ssp., Ambrosia ssp., Avena ssp., Conyza ssp., Descurainia ssp., Euphorbia ssp. and Senecio ssp.

### Claim at position 7 (depends on 16)

21: The method of claim 16, wherein the PPO resistant weeds are selected from the group consisting of Asian copperleaf, smooth pigweed, Palmer amaranth, redroot pigweed, tall/common waterhemp, common ragweed, wild oat, flixweed, wild poinsettia and Eastern groundsel.

### Claim at position 8 (depends on 16)

22: The method of claim 16, wherein the PPO resistant weeds are selected from the group consisting of Palmer amaranth, tall/common waterhemp and common ragweed.

### Claim at position 9 (depends on 16)

23: The method of claim 16, wherein the PPO resistant weeds contain a ΔG210 or R98L mutation in the Protox enzyme conferring resistance to PPO-inhibiting herbicides.

### Claim at position 10 (depends on 16)

24: The method of claim 16, wherein the compound of formula (I) is selected from the compounds of formulae (I).1 and (I.)4:

### Claim at position 11 (depends on 16)

25: The method of claim 16, wherein a herbicidal composition comprising at least one compound of formula (I), and at least one further compound selected from herbicides B and/or safeners C is applied.

### Claim at position 12 (depends on 25)

26: The method of claim 25, wherein the herbicide B is selected from the herbicides of class b1) to b15):
b1) lipid biosynthesis inhibitors;
b2) acetolactate synthase inhibitors (ALS inhibitors);
b3) photosynthesis inhibitors;
b4) protoporphyrinogen-IX oxidase inhibitors (PPO inhibitors) other than the compounds of formula (I);
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 or derivatives.

### Claim at position 13 (depends on 16)

27: The method of claim 16, wherein an agrochemical composition comprising at least one compound of formula (I) and auxiliaries customary for formulating crop protection agents, and optionally at least one further compound selected from herbicides B and/or safeners C, is applied.

### Claim at position 14 (depends on 16)

28: Method for controlling PPO resistant weeds as claimed in claim 16, wherein the compound of formula (I) is applied in a locus where PPO tolerant crops are grown.