Method for Controlling PPO Resistant Weeds

Abstract

A method for controlling PPO resistant weeds, wherein compounds of formula (I)

##STR00001## 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

1-15. (canceled)

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) ##STR00006## wherein R.sup.1 is H, F or Cl; R.sup.2 is F, Cl, Br, CN, NO.sub.2, C(O)NH.sub.2 or C(S)NH.sub.2; R.sup.3 is H or C.sub.1-C.sub.6-alkyl; R.sup.4 is H or C.sub.1-C.sub.6-alkyl; R.sup.5 is H, OH, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-alkynyl, C.sub.1-C.sub.6-haloalkyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl or C.sub.6-C.sub.10-aryl-C.sub.1-C.sub.6-alkoxy; R.sup.6 is H, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl or C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-alkyl; R.sup.7 is H, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-alkenyl, C.sub.3-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.6-C.sub.10-aryl-C.sub.1-C.sub.6-alkyl or C.sub.6-C.sub.10-aryl-C.sub.1-C.sub.6-alkoxy; W is O, S, NH or N(C.sub.1-C.sub.6-alkyl); X is C.sub.1-C.sub.6-alkylene or C.sub.1-C.sub.6-haloalkylene; and Y is O, S, S(O), S(O).sub.2, NH or N(C.sub.1-C.sub.6-alkyl); wherein the PPO resistant weeds are weeds, that are resistant to PPO-inhibiting herbicides except the compounds of formula (I); and wherein the application of the compound of formula (I) is during and/or after the emergence of the PPO resistant weeds.

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

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.

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).

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.

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.

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.

23: The method of claim 16, wherein the PPO resistant weeds contain a G210 or R98L mutation in the Protox enzyme conferring resistance to PPO-inhibiting herbicides.

24: The method of claim 16, wherein the compound of formula (I) is the compound of formula (I).1: ##STR00007##

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.

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, amides, esters or thioesters.

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.

28: The method of claim 16, wherein the compound of formula (I) is applied in a locus where PPO tolerant crops are grown.

Description

EXAMPLES

[0458] The herbicidal activity of the compound of formula (I) was demonstrated by the following experiments:

[0459] The control of resistant weeds by the compounds of formula (I) was demonstrated by the following greenhouse experiment:

[0460] The culture containers used were plastic flowerpots containing loamy sand with approximately 3.0% of humus as the substrate. The seeds of the test plants were sown separately for each species and/or resistant biotype. For the pre-emergence treatment, the active ingredients, which had been suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants had rooted. This cover caused uniform germination of the test plants, unless this had been impaired by the active ingredients. For the post-emergence treatment, the test plants were first grown to a height of 3 to 15 cm, depending on the plant habit, and only then treated with the active ingredients which had been suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment. Depending on the species, the plants were kept at 10-25 C. or 20-35 C., respectively. The test period extended over 2 to 4 weeks. During this time, the plants were tended, and their response to the individual treatments was evaluated. The evaluation was carried out by using a scale from 0 to 100. 100 means no emergence of the plants or complete destruction of at least the above-ground parts, and 0 means no damage, or normal course of growth.

[0461] The plants used in a first greenhouse experiment were of the following species and biotype:

TABLE-US-00004 weed Bayer Scientific Common no. code name name Biotype w.1 AMATA Amaranthus Common Sensitive tamariscinus waterhemp w.2 AMATA Amaranthus Common PPO resistant tamariscinus waterhemp biotype 1 w.3 AMATA Amaranthus Common PPO resistant tamariscinus waterhemp biotype 2

[0462] The results shown in the following table 2 demonstrate that compound (I).1 has very good activity on both sensitive (w.1) and resistant weeds (w.2, w.3), whereas the known PPO inhibitor azafenidin shows much weaker control of resistant in comparison to sensitive biotypes:

TABLE-US-00005 TABLE 2 Herbicide Use rate Weed control (%) compound [g/ha] w.1 w.2 w.3 (I).1 4 99 91 85 (1).1 2 90 83 78 azafenidin 4 98 73 72 azafenidin 2 95 67 70

[0463] In another greenhouse experiment, plants of the following species and biotype were tested:

TABLE-US-00006 weed Bayer Scientific Common no. code name name Biotype w.4 AMATA Amaranthus Common Sensitive tamariscinus waterhemp w.5 AMATA Amaranthus Common PPO resistant tamariscinus waterhemp biotype 3 that was confirmed to contain the G210 mutation w.6 AMATA Amaranthus Common PPO resistant tamariscinus waterhemp biotype 4 that was confirmed to contain the G210 mutation

[0464] The results shown in the following table 3 demonstrate that compound (I).1 has very good activity on both sensitive (w.4) and resistant weeds (w.5, w.6) that were shown to contain the G210 mutation:

TABLE-US-00007 TABLE 3 Herbicide Use rate Weed control (%) compound [g/ha] w.4 w.5 w.6 (I).1 4 92 95 88