WO2002102157A1

WO2002102157A1 - Benzisothiazole and benzisoxazole compounds as crop desiccants and/or defoliants

Info

Publication number: WO2002102157A1
Application number: PCT/EP2002/005914
Authority: WO
Inventors: Steven R. Busse; Brian J. Dahlke; Clark Dennis Klein, Jr.; Michael Anthony Guaciaro; Paul R. Nester; Laura Sue Quakenbush
Original assignee: Basf Aktiengesellschaft
Priority date: 2001-05-31
Filing date: 2002-05-29
Publication date: 2002-12-27

Abstract

The present invention describes herbicidal compositions, including their methods of use as crop dessicants and/or defoliants. The herbicidal compositions include an effective amount of a benzisothiazole or benzisoxazole herbicide I and an adjuvant. The present invention also describes a method of defoliating or desiccating a plant by contacting the plant with an effective amount of a benzisothiazole or benzisoxazole compound. Moreover, the present invention relates to a method of defoliating or desiccating a plant by contacting the plant with an effective amount of a composition containing a benzisothiazole or benziso-xazole compound and an adjuvant.

Description

BENZISOTHIAZOLE AND BENZISOXAZOLE COMPOUNDS AS CROP DESICCANTS AND/ OR DEFOLIANTS

The present invention relates to new herbicidal compositions and their methods of use, in particular, the present invention relates to compositions of benzisothiazole and benzisoxazole herbicides and their use as crop desiccants/defoliants .

Background of the Invention

Harvesting of certain crops may be aided by the use of substances that cause plant defoliation and/or desiccation. For example, cotton defoliation prior to harvest has several potential bene- fits. The removal of leaves eliminates the main source of stain and trash, thereby resulting in better grade cotton. In fact, mechanically harvested cotton absorbs moisture from the harvester and contains considerably more dead leaf matter than that found in hand-picked cotton. If not defoliated, this trash is particu- larly difficult to remove from the cotton. As a result, the additional moisture and trash in mechanically harvested cotton can increase cotton processing costs.

Similarly, for the harvesting of vine crops such as potatoes, vine desiccation has several benefits. For example, killing the vines stops the growth of the potatoes and hastens maturity, thereby resulting in potatoes that are easier to harvest mechanically. Killing potato vines is necessary because the tubers will more easily release/separate from the vines during mechanical harvest. This is important because the tubers will sustain less damage/bruising that will help to reduce spoilage during storage and handling. Additionally, the mechanical digging of potatoes is made easier because the tubers ripen quickly and the skins thicken after desiccation. As such, desiccation often leads to an overall cost savings.

Examples of compounds that are commonly used as cotton defoliants include S, S, S-tributyl phosphorotrithioate, also known as butifos or Def.RTM, and l-phenyl-3- (1, 2 , 3-thiadiazol-5-yl) urea, also known as thidiazuron or Dropp.RTM. Compounds that are commonly used for potato vine desiccation are 1 , 1 ' -ethylene-2 , 2 '-bipyri- dyldiylium ion as the dibromide monohydrate salt, also known as diquat, (+/-) -2-amino-4- (hydroxymethylphosphinyl)butanoic acid, also known as glufosinate, and 1 , 1 ' -dimethyl-2 , 2 ' -bipyridyldi- ylium ion as the dichloride salt, also known as paraquat. Among the limitations of some of these commonly used harvest aids is the need for high use rates. Moreover, some of the componds can be dangerous, such as paraquat, which is a restricted use chemical that poses a danger to the applicator and anyone who might enter the field for 24 hours after application. Thus, there is a continuing need for new substances that promote plant defoliation and/or desiccation.

Summary of the Invention

As embodied and broadly described herein, this invention, in one aspect, relates to a method of defoliating or desiccating a plant that includes contacting the plant with an effective amount of a benzisothiazole or benzisoxazole compound of formula (I)

wherein the substituents are described further in the detailed description.

The present invention also relates to a method of defoliating or desiccating a plant that includes contacting the plant with an effective amount of a composition containing a benzisothiazole or benzisoxazole compound of formula (I) and a surface active agent.

Advantages of the invention will be set forth in part in the description which follows, and in part will be obvious from the des- cription, or may be learned by practice of the invention. It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory only and are not restrictive of the invention, as claimed.

Detailed Description

Before the present compounds, compositions, and methods are disclosed and described, it is to be understood that this invention is not limited to specific synthetic methods of making that may of course vary. It is also to be understood that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting.

In this specification and in the claims that follow, reference will be made to a number of terms that shall be defined to have the following meanings :

The term "alkenyl" as used herein intends a branched or un- branched unsaturated hydrocarbon group containing at least one double bond, such as ethenyl, propenyl, 1-butenyl, 2-butenyl, and the like. Geometric structures such as (AB)C=C(CD) are intended to include all isomers. One or more hydrogen atoms of the alkenyl group may be replaced with one or more functional groups.

"Alkoxy" refers to an alkyl, alkenyl or alkynyl group bound through an oxygen linkage. Typical alkoxys include methoxy, ethoxy, propoxy, isopropoxy and 1, 2-dimethoxyethane . One or more hydrogen atoms of the alkyl group may be replaced with one or more functional groups .

The term "alkyl" as used herein refers to a branched or un- branched saturated hydrocarbon group, such as methyl, ethyl, n- propyl, isopropyl, n-butyl , isobutyl, t-butyl, and the like. One or more hydrogen atoms of the alkyl group may be replaced with one or more functional groups.

The term "alkynyl" as used herein refers to a branched or un- branched unsaturated hydrocarbon group containing at least one triple bond, such as ethynyl, propynyl, 1-butynyl, 2-butynyl, and the like. One or more hydrogen atoms of the alkynyl group may be replaced with one or more functional groups .

"Benzyl" and "phenyl" include single C₆H₆ aromatic rings and two or more aromatic rings in a fused or unfused state. The aromatic rings may be fused at any bond. In the phenyl group, at least one hydrogen atom is replaced with an oxygen atom. Additionally, in either the benzyl or phenyl groups, one or more hydrogen atoms may be replaced with one or more functional groups that may be present on any position, i.e. ortho, meta or para positions or fused to the cyclic structure.

"Cycloalkyl" refers to a cyclic alkyl, alkenyl or alkynyl group. One or more hydrogen atoms of the cycloalkyl group may be replaced with one or more functional groups . Such substituents may be present on any position, i.e. ortho, meta or para positions or fused to the cyclic structure. "Halogen" or "halo" will be taken to include fluoro, chloro, bromo and iodo.

"Salt" as used herein includes salts that can form with, for ex- ample, amines, alkali metal bases and alkaline earth metal bases or quaternary ammonium bases, including zwitterions. Suitable alkali metal and alkaline earth metal hydroxides as salt formers include the hydroxides of lithium, sodium, potassium, magnesium or calcium. Illustrative examples of amines suitable for forming ammonium cations are ammonia as well as primary, secondary and tertiary Ci-Cis alkylamines, C₁-C₄ hydroxyalkylamines and C₂-C₄ alkoxyalkylamines , typically methylamine, ethylamine, n-propyla- mine, isopropylamine, the four isomeric butylamines, n-amylamine, isoamylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, oc- tadecylamine, methyl ethylamine, methyl isopropylamine, methyl hexylamine, methyl nonylamine, methyl pentadecylamine, methyl oc- tadecylamine, ethyl butylamine, ethyl heptylamine, ethyl octylamine, hexyl heptylamine, hexyl octylamine, dimethylamine, diethy- lamine, di-n-propylamine, diisopropylamine, di-n-butylamine, di- n-amylamine, diisoamylamine, dihexylamine, diheptylamine, diocty- lamine, ethanolamine, n-propanolamine, isopropanolamine, N,N-die- thanolamine, N-ethylpropanolamine, N-butylethanolamine, allyl- amine, n-but-2-enylamine, n-pent-2-enylamine, 2 , 3-dimethyl- but-2-enylamine, dibut-2-enylamine, n-hex-2-enylamine, propylene- diamine, trimethylamine, triethylamine, tri-n-propylamine, triis- opropylamine, tri-n-butylamine, triisobutylamine, tri-sec-butyla- mine, tri-n-amylamine, methoxyethylamine and ethoxyethylamine; heterocyclic amines such as pyridine, quinoline, isoquinoline, morpholine, piperidine, pyrrolidine, indoline, quinuclidine and azepine; primary arylamines such as anilines, methoxyanilines, ethoxyanilines, o-, m- and p-toluidines, phenylenediamines, ben- zidines, naphthylamines and o-, m- and p-chloroanilines .

An "effective amount" means the amount of herbicidal compound and/or composition needed to achieve an observable defoliating or desiccating effect on plant leaves, vines or stems including the effects of plant necrosis as seen by browning of leaves, vines, stems and vascular areas, plant death, growth inhibition, repro- duction inhibition, inhibition of proliferation, and removal, destruction, or otherwise diminishing the occurrence and activity of a plant. One of ordinary skill in the art will recognize that the potency and, therefore, an "effective amount", can vary for the various herbicidal compounds/compositions used in the inven- tion. The overall effectiveness may be from 2 to 100% (visually determined) , which may not be realized until several days or weeks after treatment.

As used throughout, the term "contacting" is used to mean that the plant and/or the area surrounding the plant (i.e. soil, water) has contact with the present compound(s) or composition (s) by any application method known in the art. As such, "contacting" includes both direct contact (applying the compound/composition directly on the plant) and indirect contact (applying the com- pound/composition to the area surrounding the plant whereupon the plant incorporates the active ingredients) .

The term "plant" as used herein means terrestrial plants and aquatic plants, including both crop plants and weed plants. In- elusive of terrestrial plants are emerging seedlings and herbaceous vegetation including the roots and above-ground portions, as well as established woody plants. Inclusive of aquatic plants are algae, vegetative organisms free-floating and immersed species that are normally rooted in soil.

Exemplary plants include cereal crop plants (wheat, rye, barley, oats) , plantation crop plants (rubber, pineapple, coffee, bananas, tea), orchard crop trees (citrus fruit trees, apple trees, peach trees, pear trees, nut trees, gum trees, coconut trees, olive trees) , and other crop plants including, but not limited to, sunflower, alfalfa, rice, rape/canola, peas, lentils, beans, tomatoes, potatoes, corn, sorghum, radish, Chinese cabbage, cotton, sugarcane and soybeans.

A non-exhaustive list of weed-type plants includes the following genera without restriction: Abutilon, Amaranthus , Artemisia, As- clepias, Avena, Axonopus, Borreria, Brachiaria, Brassica, Bro us, Chenopodium, Cirsium, Commelina, Convolvulus, Cynodon, Cyperus, Digitaria, Echinochloa, Eleusine, Elymus, Equisetum, Erodium, He- lianthus, Imperata, Ipomoea, Kochia, Lolium, Malva, Oryza, Ot- tochloa, Panicum, Paspalum, Phalaris, Phragmites, Polygonum, Por- tulaca, Pteridium, Pueraria, Rubus, Salsola, Setaria, Sida, Sina- pis, Sorghum, Triticum, Typha, Ulex, Xanthium and Zea.

Broadleaf species are exemplified without limitation by the following: velvetleaf (Abutilon theophrasti) , pigweed (Amaranthus spp.), mugwort (Artemisia spp.), milkweed (Asclepias spp.), but- tonweed (Borreria spp.), canada thistle (Cirsium arvense) , commelina (Commelina spp.), field bindweed (Convolvulus arvensis) , fi- laree (Erodium spp.), morningglory (Ipomoea spp.), kochia (Kochia scoparia) , mallow (Malva spp.), wild buckwheat (Polygonum spp.), smartweed, etc. (Polygonum spp.), purslane (Portulaca spp.), kudzu (Pueraria spp.), russian thistle (Salsola spp.), sida (Sida spp.), wild mustard (Sinapis arvensis) and cocklebur (Xanthium spp . ) .

Narrowleaf species are exemplified without limitation by the following: wild oat (Avena fatua) , carpetgrass (Axonopus spp.), bra- chiaria (Brachiaria spp.), downy brome (Bromus tectorum) , bermu- dagrass (Cynodon dactylon) , yellow nutsedge (Cyperus esculentus) , purple nutsedge (C. rotundus) , crabgrass (Digitaria spp.), barnyardgrass (Echinochloa crus-galli) , goosegrass (Eleusine in- dica) , quackgrass (Elymus repens) , lalang (Imperata cylindrica) , annual ryegrass (Lolium multiflorum) , perennial ryegrass (Lolium perenne) , ottochloa (Ottochloa nodosa) , guineagrass (Panicum maximum) , dallisgrass (Paspalum dilatatum) , bahiagrass (Paspalum no- tatuirt) , canarygrass (Phalaris spp.), reed (Phragmites spp.), foxtail (Setaria spp.), johnsongrass (Sorghum halepense) , and cattail (Typha spp.).

Other plant species are exemplified without limitation by the following: horsetail (Equisetum spp.), bracken (Pteridium aquili- num) , blackberry (Rubus spp.), gorse (Ulex europaeus) , mosses (Byrum spp. and others) , and conifers (Pinus spp. and others) .

The benzisothiazole and benzisoxazole compounds of the present invention have the formula (I)

wherein X is 0 or S ; R¹ and R² are each independently hydrogen or halogen;

Y is R¹² , OR¹² , C (0) NR¹³R^l4 C (0) R¹⁴ , COOR¹⁹ , C (0) SR¹⁴ or C (=N0R¹⁴ ) ;

Z is 0 or S ;

Alk is C₁-C₄ alkyl ; R is C₁-C₄ haloalkyl ; R¹² is hydrogen, a Cι-C₆ alkyl or C -C₆ alkenyl group, wherein each group is optionally substituted with any combination of one to three halogen atoms, one or two Cι~C₄ alkoxy groups, one Ci-Cio haloalkoxy group, one NR¹⁵R¹⁶ group, one S(0)_q-R¹⁷ group, one or two cyano groups, one or two C(0)R¹⁸ groups, one or two COOR¹⁹ groups, one or two C(O)NR²⁰R²¹ groups, one X¹R²² group, one P(0) (OR²³)₂ group, one OC(0)R³³ group, or one phenyl group optionally substituted with any combination of one to three halogen atoms, one C₁-C₄ alkyl group, one C₁-C₄ alkoxy group or one XR²⁷ group,

one thiophene, pyridine or pyrimidine ring optionally substituted with any combination of one or two halogen atoms, one or two C₁-C₄ alkyl groups, one or two C₁-C₄ haloalkyl groups, one or two C₁-C₄ alkoxy groups or one or two C₁-C₄ haloalkoxy groups ,

one 1,3-dioxane or 1, 3-dioxolane ring optionally substituted with any combination of one to three halogen atoms, one to three C₁-C₄ alkyl groups, one to three C₁-C₄ haloalkyl groups, one to three C₁-C₄ alkoxy groups or one to three C₁-C₄ haloalkoxy groups, or

phenyl optionally substituted with any combination of one or two halogen atoms, one to three C₁-C₄ alkyl groups, one C₁-C₄ alkoxy group, one C(0)R²⁵ group, one COOR²⁶ group, one X¹R²² group, one CH=CHR²² group, one CH₂-CH (R²⁸) R²² group or one N(R²⁹)S0₂R³⁰ group;

R¹³ is hydrogen, Cι-C₆ alkoxyalkyl, C₁-C₄ alkyl, OR²³, cyano or S0₂R⁵¹;

R¹⁴ is hydrogen, Cι-C₆ alkyl, C₃-C₇ cycloalkyl, C₂-C₈ alkoxyalkyl, C₂-C₆ alkenyl, C -C₆ alkynyl or benzyl;

R¹⁵ is hydrogen,

C₁-C₄ alkyl optionally substituted with one COOR⁴² group, benzyl optionally substituted with any combination of one to three halogen atoms, one to three C₁-C₄ alkyl groups, one to three C₁-C₄ haloalkyl groups, one to three C₁-C₄ alkoxy groups or one to three C₁-C₄ haloalkoxy groups, or C(0)R⁴³;

R¹⁶ is hydrogen, C₁-C₄ alkyl, S0₂R⁴⁵, C(0)R⁴⁶, or benzyl optionally substituted with any combination of one to three halogen atoms, one to three C₁-C₄ alkyl groups, one to three C₁-C₄ haloalkyl groups, one to three C₁-C₄ alkoxy groups or one to three C₁-C₄ haloalkoxy groups;

R¹⁷, R¹⁸, R²⁵, R³⁰, R³³, R⁴⁵ and R⁵¹ are each independently NR⁶R⁴⁸,

C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₆ alkenyl optionally substituted with phenyl, benzyl optionally substituted with any combination of one to three halogen atoms, one to three C₁-C₄ alkyl groups, one to three C₁-C₄ haloalkyl groups, one to three C₁-C₄ alkoxy groups, one to three C₁-C₄ haloalkoxy groups, one nitro group, one cyano group, one OR²² or SR²² group, or phenyl optionally substituted with any combination of one to three halogen atoms, one to three C₁-C₄ alkyl groups, one to three C₁-C₄ haloalkyl groups, one to three C₁-C₄ alkoxy groups, one to three C₁-C₄ haloalkoxy groups, one nitro group, one cyano group, one OR²² or SR²² group;

R¹⁹ and R²⁶ are each independently hydrogen, C₁-C₄ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, Si(R¹)₃, benzyl, phenyl, furfuryl, pyridyl, thienyl, oximino or an alkali metal, alkaline earth metal, manganese, copper, zinc, cobalt, silver, nickel, ammonium or organic ammonium cation;

R²⁰ is hydrogen, a C₁-C₆ alkyl, C₃-C₇ cycloalkyl, C₂-C₆ alkenyl or C₂-C₆ alkynyl group wherein each group is optionally substituted with one COOR⁴² group, benzyl optionally substituted with any combination of one to three halogen atoms, one to three C₁-C₄ alkyl groups, one to three C₁-C₄ haloalkyl groups, one to three C₁-C₄ alkoxy groups or one to three C₁-C₄ haloalkoxy groups, phenyl optionally substituted with any combination of one to three halogen atoms, one to three C₁-C₄ alkyl groups, one to three C₁-C₄ haloalkyl groups, one to three C₁-C₄ alkoxy groups, one to three C₁-C₄ haloalkoxy groups, one COOR²⁶ group , C(0)R⁴³ or C0₂R⁴² ;

R²¹ is hydrogen, Cι-C₆ alkyl, C₁-C₄ alkoxy, C₃-C₇ cycloalkyl, C₂-C₆ alkenyl, C₃-C₇ cycloalkenyl, C₂-C₆ alkynyl, S0₂R⁴⁵, C(0)R⁴⁶, benzyl optionally substituted with any combination of one to three halogen atoms, one to three C₁-C₄ alkyl groups, one to three C_3.-C₄ haloalkyl groups, one to three C₁-C₄ alkoxy groups or one to three C₁-C₄ haloalkoxy groups, or phenyl optionally substituted with any combination of one to three halogen atoms, one to three C₁-C₄ alkyl groups, one to three C₁-C₄ haloalkyl groups, one to three C₁-C₄ alkoxy groups or one to three C₁-C₄ haloalkoxy groups;

R²² and R²⁷ are each independently hydrogen, C(0)R³³, S0₂R⁴⁷,

C₁-C₄ alkyl substituted with one Cι~C₆ alkoxy, COOR³², C(0)R³³, C(0)NR³⁵R³⁶, C(0)ON=CR³⁷R³⁸, C(0)NHOR²³, cyano or 2-dioxolanyl group, or one phenyl, dihydrofuranone or furanone ring whe- rein each ring is optionally substituted with any combination of one to three halogen atoms, one to three C₁-C₄ alkyl groups, one to three C₁-C₄ haloalkyl groups, one to three C₁-C₄ alkoxy groups or one to three C₁-C₄ haloalkoxy groups, C₃-C₆ alkenyl optionally substituted with one Ci-C_δ alkoxy, COOR³², C(0)R³³ or C(OR³ )₂ group, C₃-C₆ alkynyl, phenyl optionally substituted with any combination of one to three halogen atoms, one or two C₁-C₄ alkyl groups, one or two C₁-C₄ alkoxy groups, one C1.-C₄ haloalkyl group, one C₁-C₄ halo- alkoxy group, one cyano group, one nitro group, one NR³⁹R⁴⁰ group or one C(0)R³³ group, or benzyl optionally substituted on the phenyl ring with any combination of one to three halogen atoms, one or two C₁-C₄ alkyl groups, one or two C₁-C₄ alkoxy groups, one C₁-C₄ ha- loalkyl group, one C₁-C₄ haloalkoxy group, one cyano group, one nitro group, one NR³⁹R⁴⁰ group or one C(0)R³³ group;

R²³ is hydrogen or C₁-C₄ alkyl;

R²⁸ is halogen;

R²⁹ is hydrogen, C₁-C₄ alkyl or C₁-C₄ haloalkyl;

R³² is hydrogen, Si(R⁴⁷)₃,

C₁-C₄ alkyl optionally substituted with one COOR⁴⁸, OC(0)R³³ or

C₁-C₄ alkoxy group,

C₁-C₄ haloalkyl,

C₃-C₈ cycloalkyl, ₃-C₈ halocycloalkyl,

C -C₆ alkenyl optionally substituted with one phenyl group,

C₃-C₆ haloalkenyl,

C₅-C₈ cycloalkenyl,

C₅-C₈ halocycloalkenyl, C₃-C₆ alkynyl optionally substituted with one phenyl group,

C₃-C₆ haloalkynyl, benzyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, Cχ-C alkyl, C₃.-C₄ haloalkyl, C₁-C₄ alkoxy and C₁-C₄ haloalkoxy groups, phenyl optionally substituted with one or more groups inde- pendently selected from halogen, cyano, nitro, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy and C₁-C₄ haloalkoxy groups, ₁-C₄ alkyl substituted with one pyridyl, furyl, thienyl, tetrahydrofuryl or NR⁴⁹R⁵⁰ group, or an alkali metal, alkaline earth metal, manganese, copper, zinc, cobalt, silver, nickel, ammonium or organic ammonium cation;

R³⁴, R³⁷ and R³⁸ are each independently Cχ-C₆ alkyl;

R³⁵ and R⁴⁹ are each independently hydrogen or C₁-C₄ alkyl and R³⁶ and R⁵⁰ are each independently hydrogen, cyano, C₁-C₄ alkyl, S0₂R⁵¹ or phenyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy and C₁-C₄ haloalkoxy groups, or when R³⁵ and R³⁶ or R⁴⁹ and R⁵⁰ are taken together with the nitrogen atom to which they are attached, they form a 5- to 12-membered monocyclic or fused bicyclic, heterocyclic ring optionally substituted with one or more groups independently selected from halogen, cyano, nitro, amino, hydroxyl , C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy or C₁-C₄ haloalkylsulfonyl groups;

R³⁹, R⁴⁰, R⁴², R⁴³, R⁴⁶ and R⁴⁸ are each independently hydrogen, C₂-C₆ alkenyl, C₃-Cs cycloalkyl, Ci-Cβ alkyl optionally substituted with one or two C₁-C₄ alkoxy groups , benzyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy and C₁-C₄ haloalkoxy groups, or phenyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy and C₁-C₄ haloalkoxy groups, and when R⁴⁶ and R⁴⁸ are taken together with the atom to which they are attached, they form a 5- to 12-membered monocyclic or fused bicyclic, heterocyclic or cycloalkyl ring optionally substituted with one or more groups independently selected from halogen, cyano, nitro, amino, hydroxyl, C₁-C₄ alkyl, C_3.-C₄ haloalkyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy or C₁-C₄ haloalkylsulfonyl groups;

R⁴¹ and R⁴⁷ are each independently C₁-C₄ alkyl , benzyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy and C₁-C₄ haloalkoxy groups, or phenyl optionally substituted with one or more groups inde- pendently selected from halogen, cyano, nitro, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy and C₁-C₄ haloalkoxy groups;

X¹ and X² are each independently 0 or S; and q is an integer of 0, 1 or 2 ;

and the optical isomers, diastereomers and/or tautomers thereof.

Benzisothiazole and benzisoxazole compounds and their methods of making are disclosed in US 5,484,763, US 5,523,278 and US 6,156,700, all of which are incorporated by reference in their entireties for all purposes. Desirable active compounds I are those that exhibit high herbicidal effects (evaluated as ratings) at low concentrations .

Exemplary benzisothiazole and benzisoxazole compounds of formula (I) include, but are not limited to, those compounds wherein Alk is methyl; R is trifluoromethyl; R¹ is hydrogen; R² is hydrogen or fluorine; Y is R¹², COOR¹⁹, C(0)R¹⁴ or C (0)NR¹³R¹⁴; R¹² is hydrogen, Cι-C₆ alkyl optionally substituted with any combination of one to three halogen atoms, one hydroxyl group, one or two C₁-C₄ alkoxy groups, one C₁-C₄ haloalkoxy group, one S0₂R¹⁷ group, one or two cyano groups, one C(0)R¹⁸ group, one or two COOR¹⁹ groups, one or two C(O)NR²⁰R²¹ groups, one P(0) (OR²³)₂ group or one OC(0)R³³ group, C -C₆ alkenyl optionally substituted with any combination of one C(0)R¹⁸ group or one COOR¹⁹ group,

OCR56R5 _C0OR32 _OCR56_R57_C(₀)_NR35_R36

R¹³ is hydrogen, C₁-C₄ alkyl or S0₂R⁵¹; R¹⁴ is hydrogen, C₁-C₄ alkyl or benzyl; R¹⁸, R²³, R⁵⁶ and R⁵⁷ are each independently hydrogen or C₁-C₃ alkyl; R⁵², R⁵³, R⁵⁴ and R⁵⁵ are each independently hydrogen, C₁-C₃ alkyl, C₂-C₃ alkenyl, C₁-C₃ alkoxy or halogen, provided that at least one of R⁵² , R⁵³, R⁵⁴ and R⁵⁵ is hydrogen; R¹⁹ is hydrogen, C₁-C₄ alkyl , C₃-C₆ alkenyl , C₃-C₆ alkynyl , benzyl , pyridyl or an alkali metal, alkaline earth metal, ammonium or organic ammonium cation; R²² is hydrogen, C(0)R³³, S0₂R⁴⁷ , C₁-C alkyl optionally substituted with one cyano group, C₃~C₆ alkenyl or C₃-C₆ alkynyl; R³² is hydrogen, C_3.-C₄ alkyl optionally substituted with one COOR⁴⁸ or C_3.-C₄ alkoxy group, C₁-C₄ haloalkyl, C₃-C₆ alkenyl optionally substituted with one phenyl group, C₃-C₆ alkynyl optionally substituted with one phenyl group, C₁-C₄ alkyl substituted with one pyridyl, furyl, thienyl, tetrahydrofuryl or NR⁴⁹R⁵⁰ group, or an alkali metal, alkaline earth metal, ammonium or organic ammonium cation; R³⁵ and R⁴⁹ are each independently hydrogen or C₁-C₄ alkyl; R³⁶ is S0₂R⁵¹ or C₁-C₃ alkoxy; R¹⁷, R³³ and R⁵¹ are each independently C₁-C₄ alkyl, C₁-C₄ haloalkyl, NR⁶R⁴⁸, C₃-C₆ cycloalkyl or an isoxazole ring; R⁴⁶ and R⁴⁸ are each independently hydrogen, C₁-C₄ alkyl or benzyl; R⁴⁷ is C₁-C₄ alkyl; R⁵⁰ is C₁-C₄ alkyl or phenyl optionally substituted with one or more groups independently se- lected from halogen, cyano, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy and C₁-C₄ haloalkoxy groups; and X is oxygen.

Further exemplary compounds of formula (I) include substituents wherein Y is C₁-C₃ alkyl, COOR³², halomethyl, cyanomethyl,

C(CH₃)₂COOR³², C₁-C₃ alkoxyethyl, C₁-C₃ alkoxymethyl , hydroxymethyl , CHO, C(0)CH₃, CH(CH₃) (C₁-C₄ alkoxy) , C(CH₃)₂CN, CH[0(Cι-C₃- alkyl)]₂, CH₂S0₂R¹⁷, C (0)NHS0₂R⁵¹,

R⁵³, R⁵⁴, R⁵⁵ and R⁵⁶ are each independently hydrogen or methyl, provided that at least one of R⁵³ , R⁵⁴ and R⁵⁵ is hydrogen; R²² is cyanomethyl, methyl, ethyl, allyl or propargyl ; R³² is hydrogen, C₁-C₄ alkyl optionally substituted with one COOR⁴⁸ group, C₁-C₄ ha- loalkyl, C₃-C₆ alkenyl or C₃-C₆ alkynyl; and R³⁵ is hydrogen.

The benzisothiazole and benzisoxazole compounds I are suitable for the desiccation and/or defoliation of plants.

As desiccants, they are suitable, in particular, for desiccating the aerial parts of crop plants such as potatoes, oilseed rape, sunflowers and soybeans . This allows completely mechanical harvesting of these important crop plants.

It is also of economic interest to facilitate harvesting, which is made possible by concentrating, over a period of time, dehis- cence, or reducing the adherence to the tree, in citrus fruit, olives or other species and varieties of pomaceous fruit, stone fruit and nuts. The same mechanism, i.e. promotion of the forma- tion of abscission tissue between fruit or leaf and shoot of the plants, is also important for readily controllable defoliation of useful plants, in particular cotton.

Moreover, shortening the period within which the individual cot- ton plants mature results in improved fiber quality after harvesting. The compounds I, or the compositions comprising them, can be used for example in the form of ready-to-spray aqueous solutions, powders, suspensions, also highly-concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for spreading, or granules, by means of spraying, atomizing, dusting, spreading or pouring. The use forms depend on the intended aims; in any case, they should guarantee the finest possible distribution of the active compounds according to the invention.

The compounds of formula (I) may be applied alone or as desic- cant/defoliant compositions containing one or more adjuvants. A wide variety of adjuvants are known to enhance the activity of herbicides, desiccants, defoliants and other agricultural chemi- cals, including, but not limited to, surfactants, spreading agents, sticking agents, humectants, penetration agents, crop oils and crop oil/surfactant blends. Exemplary adjuvants are described in "Herbicide Adjuvants", 14 Weed Technology, 764-830 (2000), which is incorporated by reference for all purposes. The amount of adjuvant is generally any effective amount. Desirably, the amount may range from about 0.1% v/v to about 10% v/v, more desirably from about 0.1% v/v to about 1.0% v/v, or in terms of volume per hectare, from about 0.1 1/ha to about 2.0 1/ha.

Suitable surfactants include emulsifying agents and wetting agents. A wide range of surfactants is available and can be selected readily by those skilled in the art from "The Handbook of Industrial Surfactants", 2nd Edition, Gower (1997), which is incorporated herein by reference in its entirety for all purposes. Anionic, nonionic, cationic and amphoteric types, or combinations of more than one of these types, are all useful in particular situations .

Exemplary anionic surfactant classes include fatty acids (includ- ing akylated fatty acids and fatty acids derived from petroleum based crop oil products and vegetable oils such as canola, corn, sunflower and soybean oils), sulfates, sulfonates, and phosphate mono- and diesters of alcohols, alkylphenols, polyoxyethylene alcohols and polyoxyethylene alkylphenols, and carboxylates of polyoxyethylene alcohols and polyoxyethylene alkylphenols. These can be used in their acid form but are more typically used as salts, for example sodium, potassium or ammonium salts.

Among nonionic surfactants, exemplary classes include polyoxy- ethylene alkyl, alkyne, alkynyl or alkylaryl ethers, such as polyoxyethylene primary or secondary alcohols, alkylphenols or acetylenic diols; polyoxyethylene alkyl or alkyne esters, such as ethoxylated fatty acids; sorbitan alkylesters, whether ethoxy- lated or not; glyceryl alkylesters; sucrose esters;, and alkyl polyglycosides .

Cationic surfactants classes include polyoxyethylene tertiary al- kylamines or alkenylamines, such as ethoxylated fatty amines, quaternary ammonium surfactants and polyoxyethylene alkylethera- mines . Representative specific examples of such cationic surfactants include polyoxyethylene (5) cocoamine, polyoxy- ethylene (15) tallowamine, distearyldimethylammonium chloride, N-dodecylpyridine chloride and polyoxypropylene (8) ethoxytrime- thylammonium chloride. Many cationic quaternary ammonium surfactants of diverse structures are known in the art to be useful in combination with herbicides and can be used in composi- tions contemplated herein.

Suitable crop oil adjuvants include mixtures of various petroleum based oils or vegetable based oils that may be used in conjunction with a wide range of surfactants .

Suitable emulsifying agents and wetting agents include, but are not limited to, ionic and nonionic types such as polyacrylic acid salts, lignosulphonic acid salts, phenolsulphonic or naphthalene- sulphonic acids, products of polycondensation of ethylene oxide with fatty alcohols, fatty acids or fatty amines, substituted phenols (especially alkylphenols or arylphenols) , sulphonosuc- cinic acid ester salts, taurine derivatives (especially alkyl taurates) , phosphoric esters of alcohols or products of polycondensation of ethylene oxide with phenols, esters of fatty acids with polyhydric alcohols, and derivatives having sulphate, sul- phonate and phosphate groups, of the compounds above.

Compositions of the present invention may also contain a carrier. The carrier is a natural or synthetic organic or inorganic ingre- dient with which one or more of the compounds and/or compositions may be combined to facilitate dispersion of the compound/composition and contact wtih the plant. The carrier may be solid (e.g. clays, synthetic silicates, silica, resins, waxes, and combinations thereof); liquid (e.g. water, aqueous solutions, N- methylpyrrolidone, methanol, ethanol, isopropyl alcohol, acetone, butyl cellosolved, 2-ethyl-l-hexanol, cyclohexanone, methyl cellulose, polyvinyl alcohol, sodium lignin sulfonates, polymeric alkyl naphthalene sulfonates, sodium naphthalene sulfonate, poly- methylene bisnaphthalenesulfonate, sodium N-methyl-N- (long chain acid) laureates, hydrocarbons and other water-immiscible ethers, 1 1 1 1 CO Φ | β 1 4-1 f 1 t0 1 Φ ft β 4H β A Φ > . β 1 Φ 01 •H -H ø β β -H •rt - 4-1 Φ - t rd O 1 4 rH -H 1 4H td 1 td β rd O CO

^ A o -H TJ TJ -— - rd A Φ -H β -H Cn 4-> rt Φ 1 O ε -rt rd rd 4-1 r-i O o -H co 3 Φ 1 Φ β TJ rH Φ rQ 4 -H S β υ φ TJ ε 4-1 • Φ A β LO rH ft

4-1 CU _^ 4-> -rt A β LT) 4-1 -H β rH 10 A O -H Φ Pi 0 01 4-> β 01 TJ 4-1 β u Φ td ε Cn o rtJ > φ β r-i 4-> o .. 10 CO ⁽0 . β 4-> CO Φ TJ O 4H φ υ 01 td tO • - 4-1 β ø Φ 0 CO 4-> O β α. β 4-⁾ id N <* β o CN o tO Φ 0 > Φ 4H CO φ A 01 β id A rH CO φ 0 υ -H ω -H 4-1 s -H -H ⁽0 1 0 4H • _^ • β g rt & -H X tO Φ ε o 4-> β 4-1 4-1 Φ O O TJ

H υ rt rH TJ ,— ΪH rH -H _^-_^ CN 4-⁾ 4-⁾ O rH rt . — . 4H ε 4-⁾ -H to U β 4J ft β rH TJ -H - O υ g rt ε β φ 01 β Cn • _^ Φ A CO ft -Q 4H Φ 3 td 4-1 o Φ > CO φ Φ rd 01 TJ 4-1 rH td A rH α. 0 ^•H 4-t o β A o o tn -H 0 TJ s to φ υ to τ3 O β Cn _^ 01 -H 4-1 υ Cn 4-1 ø Φ O Φ Φ 4-1 u υ β Φ TJ -H Φ 4-1 υ H TJ ^— ' -Q rd 4H tO — ⁽0 φ 4-1 β rd r-i β r-i A A θ rH β

Φ TJ 4H Φ ft TJ ⁽0 υ ⁽0 β 4J ω JH rβ υ Φ td Φ υ TJ O 4-> A _^ rrj -β ε \ >H g ε ¹ — ' X β o β t rβ Φ β β 4-⁾ tO ft Φ β O Cn -H Cn β β υ rd A

4-> to 3 ⁽0 0 r-i o to υ υ Φ rd φ E→ A Φ O tO A Cn 4H O (Ω β A rd -rH td rH rd (0 4-1 u _^ o -H φ ft -rt u b 4-> -H -H 01 4J H β 4-> r -rt φ 4H & -H O ⁽0 ε A -H ø β

0 β TJ -rt rH 0 β Φ 0 rQ φ ⁽0 ft 4 • 0 ^ 4-> TJ Cn o A Φ ε β ε rt Cn CO rH \ 0 co O β O -rt Λ _^ 0 φ _^-_^ β rd rβ β -H O β φ o 4-1 0 Φ to υ β 4-> 0 TJ CO Cn 01 -rt

• _^ -■-I g υ 1 -H _*- rH β <c ⁽0 X -H Φ Φ 4-> φ . Φ -rt o cn υ Cn o -rt -rt β u β 4-1 01 4-1

. — . id H -H - TJ rθ 4H ft Φ 4 o i A β rβ β > rH o rβ o O 4H N Φ >ι tO β rH φ < td

4-1 4-1 to -Q CN rH Φ -H _^^ 3 1 . 4J β Φ 4J o β ft o 4-1 4-1 \ r-i •H - εH -H Cn r-t Φ . r-i

0 β rt •. TJ H φ 3 -Q r- to 0 o -H -H •H ft LT) -rt TJ (0 4-> 4-> 4-> rH td Cn _^ β o rd . 0

<u o to φ CN TJ ø 1 4J rH - — Φ U -H TJ A 4-1 tO O S β β -rt β β -rt Φ 0 φ υ 10 A 1 -H 1 rrj rH TJ Φ 4-1 Φ 4-⁾ tO 4-> 4-> Λ rd O β tO td A Cn Φ β & 4-1 β ε rt

Φ Φ rt -i rH o β r-i -H β rH β -rt υ β Φ rd TJ -rt rd β β O 0 O ø O

A o A β 1 1 -H 4-> β tO J -H ft Φ Ot S •H Φ O φ β 4-1 10 TJ • 4-1 -rt φ β ε 0 O -H 4-1 4H

4-> to U Φ Φ ft 1 LO φ A φ -H A -H > β H CO tO A o X O ft φ Φ id CO N rH rd υ A 4-1 rH rH 3 -β rH -H in 1 r-i 4-> g Λ 4-> 4-> t ro β -H TJ ft Φ rd 4-1 -rt -H O 01 υ φ X tO β 0 φ

0] td 01 4-⁾ Λ 1 o o -H -H ft o ω o X -H φ ft O . ε 4J 0 rd -rt • φ ft φ rH Φ υ > β o β 1 rH N rt TJ to TJ φ Φ Φ X tO ft 4-> o td id Ό td -Q r-i co iH O rβ td > -rt -H

0 co 4 o o t0 4-> 1 o β ft CO > -rt β 4-> A A rd υ TJ TJ -rt φ 4H O β ε 0 β 4->

-rH rrj Kl • - Φ CN N rH Φ Φ φ -H ε 0 -H o rβ φ rH -H -H β β Φ co £ -H ft rH o -H Cn υ

4-1 φ Φ 1 ⁽0 rH rt rt _^ ft TJ rH o rβ 4-1 - A -H ⁽0 Cn Cn Φ rH Φ ⁽0 β 3 4-> υ -H 4H rd φ

*0 rrj N 4-⁾ _^ ^•H 4H 4-> o rH rH to β tO fa 4J υ td Cn 4-> TJ rβ Λ ft O TJ 4-1 β 01 4-1 4-1 4H

H β β -H (0 rH 1 TJ 1 1 Λ 1 rO td -H tO β Φ o o ft 01 4J υ Φ td td υ ft Cn β β 4H

-H . o rH A rH rθ "3< ft ,— A 4-> . 4H Φ -H 4H Cn • o >ι rd -H rH -H g φ 0 β Φ -H Φ

CO -H ft r-i -H 1 ^ ω rH 4J β • _^ β to O A to O Cn o CN td A tO rH ft A -H 01

^■§ 4 4-> to - — A A o CN 0 Φ υ ,— Φ β Φ β o rH 4-> 01 -H 4H υ Φ φ TJ Φ TJ o Φ β rH o 4-1 4J _^ A β £ 3 TJ ε Φ

Φ A 4J φ 1 O rH ft Φ , to -H g- o β A O rd to -H . O A 01 • _^ rd 0 β 01 0 φ β υ -H φ O 4-⁾ co β rH 4J 4-1 01 4-1 o ^ 01 CO rH 01 O Φ rH ft ω rd rl > 4-1 tf rd ε ro r-i 1 A X υ Φ 4-⁾ -H O -i β O 3 4-1 En 3 Cn ⁽0 φ ft TJ A υ 3

TJ β -H A ffi r-i

& δ o 01 to 01 4-> ⁽0 -H -rt Φ 4-⁾ O 10 β Φ -rt β ε o -H EH β Φ β β rrj -rt Φ Φ TJ CN υ rH rt CO -H r 4-> . A A Φ 4-⁾ . β -H A TJ φ rH r-i -H A β -H rd υ rH ft 1 1 1 4-> X TJ o υ TJ O 01 4-1 β TJ -H 4-> o rd \ β rd 4-1 O TJ υ X O 0 4-1 O co ft ø Tj rH CN o 3 0 4-1 -H φ ft O -rl tO Φ to O A Cn 0 4-1 β ε 0 w υ r-i 4-1 -H 4-1

TJ -H to rH - — X Λ rβ A rd r- 0) ε ft ^•s υ -rt 0 rd >ι & -rt φ r-t co 01 O β 4H 4-1 β co -H -β fO to 1 1 0 -H 4-> rH 3 O rH ft Φ rH o 0 O rd Φ

0) ro 1 Φ 1 3 £ υ ε O TJ β ft ε O Cn rQ . ε -i -H r V . r-i β

4-> X TJ rd rH rO 0 -rl TJ β to φ 01 Cn ft td O υ 01 β & Φ β — ' 1 1 un 4-1 o φ υ φ 0 ft 0 φ β rd o υ υ Φ Φ -H 4 4H 4-1 rH A o 1 1 ε ^»" tn

1 1 Φ ε 01 -H φ o -H 4H to A rH A A TJ 4J -H to υ A -H in rd TJ β 4H β 4-1 to β rH rt

4-1 rH o υ 4J rH CΛ ^ o rt Φ rd ⁽0 4-⁾ ^ 4J TJ -H rH 4H Cn co Φ 0 φ O A Φ O ft ft

Φ 0 - 3 ⁽0 β o - 1 β rd A φ β TJ o 0 CO 4-1 tO β rH 4-1 Cn A Cn 4-1 4-1 ε Φ -H ft ; Ό to 4-1 A to Φ -i A CO 0 •rt A υ rθ rβ Φ β TJ _^ r-i φ 3 β o -H υ β ⁽0 rd Φ > 4-1 td Φ β β to 5^ A A 4J _^ g 4-> -H ε 4-> 4 > ⁽0 β β υ TJ 0 0 4 β Φ T ε TJ -H -H A

TJ rrj o - ⁽0 to ⁽0 a υ Φ CΛ 0 to ^■s TJ υ β 3 O β A -H Φ -H Cn Cn co Cn φ 1 β 4-1 01 4H rr- a oi 4-> 4-> rt 1 1 g ^— - r-i 1 0 | 01 co S tn -H co O -H -H tO 4-1 01 > td β β 4-1 £ rd υ O O

IΛ rd TJ 4J 4 o β rd -i CN 1 A CN ro 4 Φ β 4-1 ft 4-> _^-_^ ft β -H TJ •<H β -H ^■rt Φ ft rd f •H β ft rrj ft r 01 υ 1 Dl β TJ TJ -rt CO β o O 4-1 Φ Cn β rd H

0) r-i ω φ υ r-i 1 o 1 . — . CN φ I Φ φ -rt φ ε (0 φ N o υ 4-1 rH -H υ TJ β Φ TJ Φ - ε rH 4 H rH O 4H ε 01 o O TJ ε

VH o 0 -H υ β 0 4H m 1 4 1 -H φ rQ A -H υ -rt β td A 4-1 rd TJ -rt X -H Φ -i 0 β Φ id u o 01 ϊ Q) CO & TJ <0 . — . 0 A -rt ^— * ^ β Φ TJ > id 4-⁾ TJ H 3 4-1 rd φ -H ⁽0 ε υ X υ td A A β o 4 g Φ Φ to β 4-1 TJ 4J 1 + tO β Φ O Φ Φ ft o υ A 01 φ Jo 0 4H 4-1 rβ φ 4-1 O o 01 4H o Φ o ø JE 3 n ' — rH ιϋ rt rQ ft Φ 4H A ft ε φ -rl 4-1 O A φ O rβ -H -H O r-i 4J β Cn A φ -rt u 0 u Cn 0 TJ -H N A A ft 4-> Cn rd ω O Cn 4-⁾ rd A to O ft 4-1 A 4H 4-1 4-1 β Cn Φ rd M ε

not limited to, suspension concentrated and diluted solutions, powders and emulsifications .

Suspension concentrated and diluted solutions can be prepared by mixing together the components of a composition of this invention with a liquid carrier to obtain the desired concentration. In general, concentrated solutions are sold commercially and may be mixed with water by the end user, thereby creating a dilute solution. The amounts of herbicide that are optimal in the concen- trated solution depends on the application method, the type of the herbicide used, as well as on the nature of the plant stand to be treated, and they can be determined in each individual case by suitable preliminary experiments. The concentration of herbicide compound in the concentrated solution may be in the range of about 50 g of active ingredient/1 of solution ("g/1") to about 800 g/1, desirably, from about 75 g/1 to about 250 g/1, more desirably from about 100 g/1 to about 150 g/1.

The application of an effective amount of the active ingredients of this invention to the target plant is dependent upon the response desired in the plant as well as such other factors as the plant species and stage of development thereof, the amount of rainfall, and the specific herbicide employed. In treatment of terrestrial plants, the active ingredient is desirably applied in amounts totaling from about 0.1 g/ha (also known as gms ai/ha or grams of active ingredient per hectare) to about 5000 g/ha, in particular, single applications of the active ingredient are desirably applied in amounts from about 0.1 g/ha to about 500 g/ha per application, more desirably from about 0.5 g/ha to about 280 g/ha, even more desirably from about 1.0 g/ha to about 100 g/ha, and even more desirably from about 2.0 g/ha to about 32.0 g/ha. In split or multiple treatments, the active ingredient is desirably applied at a rate of about 0.1 g/ha to about 250 g/ha for each application, more desirably from about 0.2 g/ha to about 140 g/ha. In such split or multiple treatments, the active ingredient does not need to be applied at the same rate or amount for each treatment. In applications for aquatic plants, the active ingredient is desirably applied in amounts of from about 0.01 parts per million to about 1000 parts per million, based on the aquatic medium.

Powder compositions containing one or more compounds I of the present invention, a carrier, an inert solid extender and one or more wetting agents are also part of the present invention. The inert solid extenders are usually of mineral origin such as the natural clays, diatomaceous earth and synthetic materials derived from silica and the like. Examples of such extenders include, but are not limited to, kaolinites, attapulgite clay and synthetic magnesium silicate. The powders of this invention usually contain from about 5% to about 95% of herbicide, from about 0.25% to about 25% of carrier, from about 0.25% to about 25% of surfactant and/or wetting agent and from about 4.5% to about 94.5% of inert solid extender, all percents being by weight of the total compositions .

Emulsifications are usually solutions of one or more compounds I in water-immiscible or partially water-immiscible solvents as the carrier together with at least one surface active agent. Suitable solvents for the active ingredients of this invention include, but are not limited to, hydrocarbons and water-immiscible ethers, esters or ketones . The emulsification compositions generally con- tain from about 5% to about 95% herbicide, from about 1% to about 50% adjuvant (including surfactants and emulsifying agents) , and from about 4% to about 94% carrier, all percents being by weight based on the total weight of the composition.

The compounds useful in compositions of the present invention may be readily synthesized using techniques generally known to synthetic organic chemists. In general, the compounds may be made using the procedures taught in US 5,484,763, US 5,523,278 and US 6,156,700. The compositions may be prepared in known manner, for example by homogeneously mixing or grinding the active ingredients with other ingredients. Additional components may be admixed with the composition at any point during the process, including during and/or after any mixing step of the herbicide and surface active agent.

When operating in accordance with the present invention, a plant is defoliated and/or desiccated by contacting the plant with an effective amount of the compound(s) and/or composition (s) of the present invention. The application of such compound ( s) /composi- tion(s) to terrestrial plants can be carried out by conventional methods, e.g. power dusters, boom and hand sprayers and spray dusters. The compound (s) /composition (s) can also be applied from airplanes as a dust or a spray because of their effectiveness at low dosages. The application to aquatic plants is usually carried out by spraying the active ingredient on the aquatic plants in the area where control of the aquatic plants is desired.

As a preharvest desiccant/defoliant aid, applications are made prior to harvest. The number of days between application of the desiccant/defoliant and harvest of the crop may be between 1 day and 30 days, such as 1 day, 2 days, 3 days, 5 days, 7 days, 10 days, 12 days, 14 days, 21 days and 30 days, desirably 4 days, 7 days or 14 days .

As a dry-down aid for foilage crops such as alfalfa, such ap- plications typically are applied after emergence of the plant from the soil ("POST") and either before or after cutting the plant. If applied before cutting the plant, the number of days between application of the herbicide to the plant may be between 0 days (applied within 24 hours of cutting the plant) and 30 days, such as at 0 days, 1 day, 2 days, 3 days, 5 days, 7 days, 10 days, 12 days, 14 days, 21 days or 30 days, desirably at 0 days, 1 day, 2 days, 7 days or 14 days, and more desirably at 0 days , 1 day or 7 days .

Throughout this application, various publications are referenced. The disclosures of these publications in their entireties are hereby incorporated by reference into this application for all purposes .

It will be apparent to those skilled in the art that various modifications and variations can be made in the present invention without departing from the scope or spirit of the invention. Other embodiments of the invention will be apparent to those skilled in the art from consideration of the specification and practice of the invention disclosed herein.

Use examples (desiccant/defoliant activity)

The test plants used were young cotton plants having 4 leaves (without cotyledon) which were grown under greenhouse conditions (rel. atmospheric humidity 50-70%; temperature by day/by night 27/20°C) .

The leaves of the young cotton plants were treated to runoff point with aqueous preparations of the active compounds (with addition of 0.15% by weight of the fatty alcohol alkoxylate Plurafac LF 700¹' , based on the spray liquor) . The amount of water applied was 1000 1/ha (converted) . After 13 days, the number of leaves which had been shed and the degree of defoliation in % were determined.

In the untreated control plants, no defoliation was observed.

a low-foam nonionic surfactant from BASF AG

Claims

A method of defoliating or desiccating a plant comprising contacting the plant with an effective amount of a benzisothiazole or benzisoxazole compound of the formula (I)

wherein

X is oxygen or sulfur;

Alk is Cι-C₄-alkyl ;

R is Cι-C₄-haloalkyl;

R¹ and R² are each independently hydrogen or halogen;

Y is R¹², OR¹², C(0)NR¹³R¹⁴, C(0)R¹⁴, COOR¹⁹, C(0)SR¹⁴ or

C(=N0R¹⁴) ; Z is oxygen or sulfur;

R¹² is hydrogen, a Ci-C_δ-alkyl or C₂-C₆-alkenyl group, wherein each group is optionally substituted with any combination of one to three halogen atoms, one or two Cι-C₄-alkoxy groups, one Cι-Cιo-haloalkoxy group, one NR¹⁵R¹⁶ group, one S(0)_gR¹⁷ group, one or two cyano groups, one or two C(0)R¹⁸ groups, one or two COOR¹⁹ groups, one or two C(O)NR²⁰R²¹ groups, one X¹R²² group, one P(0) (OR²³) group, one OC(0)R³³ group, or one phenyl group optionally substituted with any combination of one to three halogen atoms, one C]_-C₄-alkyl group, one Cι-C₄-alkoxy group or one X²R²⁷ grou , one thiophene, pyridine or pyrimidine ring optionally substituted with any combination of one or two halogen atoms, one or two Cι-C₄-alkyl groups, one or two Cι-C₄~ha- loalkyl groups , one or two Cι-C₄~alkoxy groups or one or two Cι-C₄-haloalkoxy groups, one 1,3-dioxane or 1, 3-dioxolane ring optionally substituted with any combination of one to three halogen atoms, one to three Cι-C₄-alkyl groups, one to three C].-C₄-ha- loalkyl groups, one to three Cχ-C -alkoxy groups or one to three Cι-C₄-haloalkoxy groups, or phenyl optionally substituted with any combination of one or two halogen atoms, one to three Cι-C₄-alkyl groups, one Cι-C₄-alkoxy group, one C(0)R²⁵ group, one COOR²⁶ group, one X¹R²² group, one CH=CHR²² group, one CH₂CH(R²⁸)R²² group or one N(R²⁹)S0₂R³⁰ group;

R¹³ is hydrogen, cyano, Ci-Cβ-alkoxyalkyl, Cι-C₄-alkyl, OR²³ or S0₂R⁵¹; R¹⁴ is hydrogen, Ci-Cβ-alkyl, C₃-C₇-cycloalkyl, C₂-Cs-alkoxy- alkyl, C -C₆-alkenyl , C -C₆-alkynyl or benzyl; R¹⁵ is hydrogen,

Cι~C₄-al yl optionally substituted with one COOR⁴² group, benzyl optionally substituted with any combination of one to three halogen atoms, one to three Cι-C₄-alkyl groups, one to three Cι-C₄-haloalkyl groups, one to three C]_-C₄-alkoxy groups or one to three Cι-C₄-haloalkoxy groups, or C(0)R⁴³; R¹⁶ is hydrogen, Cι-C₄-alkyl, S0₂R⁴⁵, C(0)R⁴⁶, or benzyl optionally substituted with any combination of one to three halogen atoms, one to three Cχ-C₄-alkyl groups, one to three Cι-C₄-haloalkyl groups, one to three

Cι-C₄-alkoxy groups or one to three Cχ-C₄-haloalkoxy groups ; R¹⁷, R¹⁸, R²⁵, R³⁰, R³³, R⁴⁵ and R⁵¹ are each independently

_NR ⁴⁶ _R ⁴8 Cι-C₄-alkyl, C₁-C₄-haloalkyl , C₂-C₆-alkenyl optio- nally substituted with phenyl, benzyl optionally substituted with any combination of one to three halogen atoms, one to three Cι-C₄-alkyl groups, one to three Cι-C₄-haloalkyl groups, one to three Cι-C₄-alkoxy groups, one to three Cι-C₄-haloalkoxy groups, one nitro group, one cyano group, one OR²² or SR²² group, or phenyl optionally substituted with any combination of one to three halogen atoms, one to three Cι-C₄~alkyl groups, one to three Cι-C₄~haloalkyl groups, one to three Cι-C₄-alkoxy groups, one to three Cι~C₄-haloalkoxy groups, one nitro group, one cyano group, one OR²² or SR²² group;

R¹⁹ and R²⁶ are each independently hydrogen, Cι-C₄-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, Si(R⁴¹)₃, benzyl, phenyl, furfuryl, pyridyl, thienyl, oximino or an alkali metal, alkaline earth metal, manganese, copper, zinc, cobalt, silver, nickel, ammonium or organic ammonium cation; R²⁰ is hydrogen, a Ci-Cg-alkyl, C₃-C₇-cycloalkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl group wherein each group is optionally substituted with one COOR⁴² group, benzyl optionally substituted with any combination of one to three halogen atoms, one to three Cι-C₄-alkyl groups, one to three Cι-C₄-haloalkyl groups , one to three Cι-C₄-alkoxy groups or one to three Cι-C₄~haloalkoxy groups , phenyl optionally substituted with any combination of one to three halogen atoms, one to three Cι-C₄-alkyl groups, one to three Cι-C₄-haloalkyl groups, one to three Cι-C₄~alkoxy groups, one to three Cχ-C₄-haloalkoxy groups, one COOR²⁶ group, C(0)R⁴³ or COOR⁴²;

R²¹ is hydrogen, Cι-C₆-alkyl, Cι-C₄~alkoxy, C₃~C -cycloalkyl , C₂-C₆-alkenyl, C₃-C₇-cycloalkenyl, C₂-C₆-alkynyl, S0₂R⁴⁵, C(0)R⁴⁶, benzyl optionally substituted with any combination of one to three halogen atoms, one to three Cι-C₄-alkyl groups, one to three Cι~C₄-haloalkyl groups, one to three Cι-C₄-alkoxy groups or one to three Cι-C₄-haloalkoxy groups , or phenyl optionally substituted with any combination of one to three halogen atoms, one to three Cι-C₄-alkyl groups, one to three Cι-C₄~haloalkyl groups, one to three C]_-C₄-alkoxy groups or one to three Cι~C₄-haloalkoxy groups ; R²² and R²⁷ are each independently hydrogen, C(0)R³³, S0₂R⁴⁷, Cι-C₄-alkyl substituted with one Cι-C₆-alkoxy, COOR³², C(0)R³³, C(0)NR³⁵R³⁶, C(0)ON=CR³⁷R³⁸, C(0)NHOR²³, cyano or 2-dioxolanyl group, or one phenyl, dihydrofuranone or furanone ring wherein each ring is optionally substituted with any combination of one to three halogen atoms, one to three Cι-C₄-alkyl groups, one to three Cι-C₄-haloalkyl groups, one to three Cι-C₄~alkoxy groups or one to three Cι-C₄-haloalkoxy groups, C₃-C₆~alkenyl optionally substituted with one Cι-C₆-alkoxy, COOR³², C(0)R³³ or C(OR³⁴)₂ group,

C₃-C₆-alkynyl, phenyl optionally substituted with any combination of one to three halogen atoms, one or two Cι-C₄-alkyl groups, one or two Cι-C₄~alkoxy groups, one Cι-C₄-haloalkyl group, one Cι~C₄-haloalkoxy group, one cyano group, one nitro group, one NR³⁹R⁴⁰ group or one C(0)R³³ group, or benzyl optionally substituted on the phenyl ring with any combination of one to three halogen atoms, one or two Cι-C₄-alkyl groups, one or two Cι~C₄-alkoxy groups, one C]_-C₄-haloalkyl group, one Cι~C₄-haloalkoxy group, one cyano group, one nitro group, one NR³⁹R⁴⁰ group or one

C(0)R³³ group;

R²³ is hydrogen or Cχ-C₄-alkyl ;

R²⁸ is halogen;

R²⁹ is hydrogen, Cι-C₄-alkyl or Cι-C₄-haloalkyl ;

R³² is hydrogen,

Si(R⁴⁷⁾ ₃,

Cχ-C₄-alkyl optionally substituted with one COOR⁴⁸,

OC(0)R³³ or Cι-C₄-alkoxy group, Cι-C₄-haloalkyl,

C₃-C₈-cycloalkyl , C -C₈-halocycloalkyl ,

C₃-C₆-alkenyl optionally substituted with one phenyl group, C₃-C₆-haloalkenyl,

Cs-Cβ-cycloalkenyl , Cs-Cs-halocycloalkenyl ,

C₃-C₆-alkynyl optionally substituted with one phenyl group, C₃-C₆-haloalkynyl, benzyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, Cι-C -alkyl, Cι-C₄-haloalkyl, Cι-C₄-alkoxy and Cι-C₄-haloalkoxy groups, phenyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, Cι~C₄-alkyl, Cι-C₄~haloalkyl , Cι-C₄-alkoxy and Cι-C₄-haloalkoxy groups, C]_-C₄-alkyl substituted with one pyridyl, furyl, thienyl, tetrahydrofuryl or NR⁴⁹R⁵⁰ group, or an alkali metal, alkaline earth metal, manganese, copper, zinc, cobalt, silver, nickel, ammonium or organic ammonium cation; R³⁴, R³⁷ and R³⁸ are each independently Cι-C₆-alkyl; R³⁵ and R⁴⁹ are each independently hydrogen or Cι~C₄-alkyl and R³⁶ and R⁵⁰ are each independently hydrogen, cyano, Cι-C₄-alkyl, S0R⁵¹ or phenyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, Cι-C₄-alkyl, Cι-C₄-haloalkyl, C]_-C₄-alkoxy and Cι~C₄-haloalkoxy groups, or when R³⁵ and R³⁶ or R⁴⁹ and

R⁵⁰ are taken together with the nitrogen atom to which they are attached, they form a 5- to 12-membered mono- cyclic or fused bicyclic, heterocyclic ring optionally substituted with one or more groups independently selected from halogen, cyano, nitro, amino, hydroxyl, Cι-C₄-alkyl, Cι-C₄-haloalkyl , Cι-C₄-alkoxy, Cι-C₄-haloalkoxy or Cι-C₄-haloalkylsulfonyl groups;

R³⁹, R⁴⁰, R⁴², R⁴³, R⁴⁶ and R⁴⁸ are each independently hydrogen, C₂-C₆-alkenyl, C₃-Cs-cycloalkyl ,

Ci-Cs-alkyl optionally substituted with one or two Cι-C₄-alkoxy groups, benzyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, Cι-C₄-alkyl, Cι-C₄-haloalkyl , Cι~C₄-alkoxy and Cι-C₄~haloalkoxy groups, or phenyl optionally substituted with one or more groups in- dependently selected from halogen, cyano, nitro,

Cι-C₄-alkyl, C_!-C₄-haloalkyl , Ci^-alkoxy and Cι-C₄-haloalkoxy groups, and when R⁴⁶ and R⁴⁸ are taken together with the atom to which they are attached, they form a 5- to 12-membered mono- cyclic or fused bicyclic, heterocyclic or cycloalkyl ring optionally substituted with one or more groups independently selected from halogen, cyano, nitro, amino, hydroxyl, Cι-C₄-alkyl, Cι-C₄-haloalkyl, Cι~C₄-alkoxy, Cι-C₄-haloalkoxy or Cι-C₄-haloalkylsulfonyl groups; R⁴¹ and R⁴⁷ are each independently C_3.-C₄-alkyl, benzyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, Cι-C₄-alkyl, Cχ-C₄-haloalkyl , C]_-C₄-alkoxy and Cι-C₄~haloalkoxy groups, or phenyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C]_-C₄-alkyl, Cι-C₄-haloalkyl , Ci-C₄~alkoxy and Cι-C₄~haloalkoxy groups;

X¹ and X² are each independently oxygen or sulfur; q is an integer of 0, 1 or 2 ; and the optical isomers, diastereomers and/or tautomers thereof .

2. The method of claim 1, wherein:

X is oxygen; Alk is methyl; R is trifluoromethyl; R¹ is hydrogen;

R² is hydrogen or fluorine; is R¹², COOR¹⁹, C(0)R¹⁴ or C (0)NR¹³R¹⁴;

R¹² is hydrogen,

Ci-Cg-alkyl optionally substituted with any combination of one to three halogen atoms, one hydroxyl group, one or two Cι~C₄-alkoxy groups, one Cι-C₄-haloalkoxy group, one S0R¹⁷ group, one or two cyano groups, one C(0)R¹⁸ group, one or two COOR¹⁹ groups, one or two C(O)NR²⁰R²¹ groups, one P(O) (OR²³) ₂ group or one OC(0)R³³ group, C₂-C₆-alkenyl optionally substituted with any combination of one C(0)R¹⁸ group or one COOR¹⁹ group,

R¹³ is hydrogen, Cι-C -alkyl or S0₂R⁵¹; R¹⁴ is hydrogen, Cι-C₄-alkyl or benzyl ;

R¹⁸ , R²³ , R⁵⁶ and R⁵⁷ are each independently hydrogen or

C₁-C₃ -alkyl ; R⁵² , R⁵³ , R⁵⁴ and R⁵⁵ are each independently hydrogen,

Cι-C₃-alkyl , C₂ -C₃ -alkenyl , Cι-C₃-alkoxy or halogen, pro- vided that at least one of R⁵² , R⁵³ , R⁵⁴ and R⁵⁵ is hydrogen; R¹⁹ is hydrogen, Cι-C -alkyl, C₃-C₆-alkenyl , C₃-C₆-alkynyl, benzyl, pyridyl or an alkali metal, alkaline earth metal, ammonium or organic ammonium cation; R²² is hydrogen, C(0)R³³, S0₂R⁴⁷, Cχ-0₄-alkyl optionally sub- stituted with one cyano group, C₃-C₆-alkenyl, or C₃-C₆-al- kynyl ; R³² is hydrogen,

Cι~C₄-alkyl optionally substituted with one COOR⁴⁸ or

Cι-C₄~alkoxy group, Cι-C -haloalkyl,

C₃-C₆-alkenyl optionally substituted with one phenyl group,

C₃-C₆-alkynyl optionally substituted with one phenyl group, Cι~C₄-alkyl substituted with one pyridyl, furyl , thienyl, tetrahydrofuryl or NR⁴⁹R⁵⁰ group, or an alkali metal, alkaline earth metal, ammonium or organic ammonium cation; R³⁵ and R⁴⁹ are each independently hydrogen or Cχ-C₄-alkyl; R³⁶ is S0₂R⁵¹ or Cι-C₃-alkoxy;

R¹⁷, R³³ and R⁵¹ are each independently Cι-C₄~alkyl,

Cι-C₄-haloalkyl, NR⁴⁶R⁴⁸, C₃-C₆-cycloalkyl or an isoxazole ring; R⁴⁶ and R⁴⁸ are each independently hydrogen, Cι-C₄~alkyl or benzyl ;

R⁴⁷ is Cι-C₄-alkyl;

R⁵⁰ is Cι-C₄~alkyl or phenyl optionally substituted with one or more groups independently selected from halogen, cyano, Cι-C₄-alkyl, Cι-C₄-haloalkyl , Cι~C₄-alkoxy and Cι-C₄~haloalkoxy groups.

3. The method of claim 1, wherein:

Y is Cι-C₃-alkyl, COOR³², halomethyl, cyanomethyl, C(CH₃)₂-COOR³², Cι-C₃-alkoxyethyl, Cι-C₃-alkoxymethyl, hydroxy- methyl, CHO, C(0)CH₃, CH (CH₃) (Cι-C -alkoxy) , C(CH₃)₂-CN, CH[0(Cι-C₃-alkyl) ]₂, CH₂-S0₂R¹⁷, C (0)NH-S0₂R⁵¹,

or OR²²

10

R⁵³, R⁵⁴, R⁵⁵ and R⁵⁶ are each independently hydrogen or methyl, provided that at least one of R⁵³, R⁵⁴ and R⁵⁵ is hydrogen;

15 R²² is cyanomethyl, methyl, ethyl, allyl or propargyl ;

R³² is hydrogen, Cι-C₄-alkyl optionally substituted with one COOR⁴⁸ group, Cι-C -haloalkyl, C₃-C₆-alkenyl or C₃-C₆-alky- nyl; and

R³⁵ is hydrogen.

20

The method of claim 1, wherein the plant is alfalfa, cotton, potato, pea, lentil or soybean.

The method of claim 1, wherein the compound is applied at a

25 rate from about 0.1 g/ha to about 500 g/ha.

6. The method of claim 1, wherein the compound is applied at a rate from about 1.0 g/ha to about 100 g/ha.

30 7. The method of claim 1, wherein the compound is sprayed onto the plant 0 days, 1 day, 2 days, 7 days or 14 days before harvesting or cutting the plant.

The method of claim 1, wherein the compound I desiccates the

35 plant .

9. The method of claim 1, wherein the compound I defoliates the plant .

40 10. A method of defoliating or desiccating a plant comprising contacting the plant with an effective amount of a composition comprising:

a) a benzisothiazole or benzisoxazole compound of formula 45 (I)

wherein

X is oxygen or sulfur;

Alk is Cι-C -alkyl;

R is Cι-C₄-haloalkyl;

R¹ and R² are each independently hydrogen or halogen;

Y is R¹², OR¹², C(0)NR¹³R¹⁴, C(0)R¹⁴, COOR¹⁹, C(0)SR¹⁴ or

C(=N0R¹⁴) ; Z is oxygen or sulfur;

R¹² is hydrogen, a Cι-C₆-alkyl or C -C₆-alkenyl group, wherein each group is optionally substituted with any combination of one to three halogen atoms, one or two Cι~C₄-alkoxy groups, one Ci-Cio-haloalkoxy group, one NR¹⁵R¹⁶ group, one S(0)_gR¹⁷ group, one or two cyano groups, one or two C(0)R¹⁸ groups, one or two COOR¹⁹ groups, one or two C(O)NR²⁰R²¹ groups, one X^-R²² group, one P(0) (OR²³)₂ group, one OC(0)R³³ group, or one phenyl group optionally substituted with any combination of one to three halogen atoms, one Cι-C₄-alkyl group, one Cι-C₄-alkoxy group or one X²R²⁷ group, one thiophene, pyridine or pyrimidine ring optionally substituted with any combination of one or two halogen atoms, one or two Cι~C -alkyl groups, one or two C]_-C₄-haloalkyl groups, one or two Cι-C₄-alkoxy groups or one or two Cι-C₄-haloalkoxy groups, one 1,3-dioxane or 1 , 3-dioxolane ring optionally substituted with any combination of one to three halogen atoms , one to three Cι-C₄-alkyl groups , one to three Cι-C₄~haloalkyl groups, one to three Cχ-C₄-alkoxy groups or one to three Cι-C₄-haloalkoxy groups, or phenyl optionally substituted with any combination of one or two halogen atoms, one to three Cι~C₄-alkyl groups, one Cι-C₄-alkoxy group, one C(0)R²⁵ group, one COOR²⁶ group , one X^XR²² group , one CH=CHR²² group , one CH₂-CH (R²⁸ ) R²² group or one N (R²⁹ ) S0₂R³⁰ group ;

R¹³ is hydrogen, cyano , Ci-Cg-alkoxyalkyl , Cι-C₄-alkyl , OR²³ or S0₂R⁵¹ ;

R¹⁴ is hydrogen, Cι-C₆-alkyl , C₃-C₇-cycloalkyl , C₂-Cs-alk- oxyalkyl , C -C₆-alkenyl , C -C₆-alkynyl or benzyl ; R¹⁵ is hydrogen,

Cι-C -alkyl optionally substituted with one COOR⁴² group , benzyl optionally substituted with any combination of one to three halogen atoms, one to three Cι-C₄-alkyl groups, one to three Cχ-C₄-haloalkyl groups, one to three Cι-C₄-alkoxy groups or one to three Cι-C₄~haloalkoxy groups, or

C(0)R⁴³; _R16 i_s hydrogen, Cι-C -alkyl, S0₂R⁴⁵, C(0)R⁴⁶, or benzyl optionally substituted with any combination of one to three halogen atoms, one to three Cχ-C₄-alkyl groups, one to three Cι-C₄-haloalkyl groups, one to three C₁-C₄-alkoxy groups or one to three Cι~C₄-haloalkoxy groups; R¹⁷, R¹⁸, R²⁵, R³⁰, R³³, R⁴⁵ and R⁵¹ are each independently NR⁴⁶R⁴⁸, Cι-C₄-alkyl, C_x-C₄-haloalkyl, C₂-C₆-alkenyl optionally substituted with phenyl, benzyl optionally substituted with any combination of one to three halogen atoms, one to three Cι-C₄~alkyl groups, one to three Cι-C₄-haloalkyl groups, one to three Cι~C₄-alkoxy groups, one to three Cι-C₄-haloalkoxy groups, one nitro group, one cyano group, one OR²² group or one SR²² group, or phenyl optionally substituted with any combination of one to three halogen atoms, one to three Cι-C₄~alkyl groups, one to three Cι-C₄~haloalkyl groups, one to three Cι-C₄~alkoxy groups, one to three

Cι-C₄-haloalkoxy groups, one nitro group, one cyano group, one OR²² group or one SR²² group;

R¹⁹ and R²⁶ are each independently hydrogen, Cι-C₄~alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl , Si(R⁴¹)₃, benzyl, phenyl, furfuryl, pyridyl, thienyl, oximino or an alkali metal, alkaline earth metal, manganese, copper, zinc, cobalt, silver, nickel, ammonium or organic ammonium cation; R²⁰ is hydrogen, a Ci-Cβ-alkyl, C₃-C₇-cycloalkyl , C -C₆-alkenyl or C₂-C₆-alkynyl group wherein each group is optionally substituted with one COOR⁴² group, benzyl optionally substituted with any combination of one to three halogen atoms, one to three Cι-C₄~alkyl groups, one to three Cι-C₄-haloalkyl groups, one to three Cι-C₄-alkoxy groups or one to three Cι-C₄-haloalkoxy groups, phenyl optionally substituted with any combination of one to three halogen atoms, one to three Cι-C₄-alkyl groups, one to three C]_-C₄-haloalkyl groups, one to three Cχ-C₄-alkoxy groups , one to three Cι-C₄-haloalkoxy groups, one COOR²⁶ group, C(0)R⁴³ or COOR⁴²;

R²¹ is hydrogen, Ci-Cβ-alkyl, Cι-C₄-alkoxy, C₃-C₇-cyclo- alkyl, C₂-C₆-alkenyl, C₃-C₇-cycloalkenyl , C₂-C₆-alky- nyl, S0₂R⁴⁵, C(0)R⁴⁶, benzyl optionally substituted with any combination of one to three halogen atoms, one to three Cι-C₄-alkyl groups, one to three Cι-C₄~haloalkyl groups, one to three Cι-C₄-alkoxy groups or one to three C]_-C₄-haloalkoxy groups, or phenyl optionally substituted with any combination of one to three halogen atoms, one to three Cι-C₄-alkyl groups, one to three Cι-C₄-haloalkyl groups, one to three Cι-C₄-alkoxy groups or one to three Cι-C₄-haloalkoxy groups ; R²² and R²⁷ are each independently hydrogen, C(0)R³³,

S0₂R⁴⁷ ,

Cι-C₄-alkyl substituted with one Cι-C₆-alkoxy, COOR³², C(0)R³³, C(0)NR³⁵R³⁶, C(0)ON=CR³⁷R³⁸, C(0)NHOR²³, cyano or 2-dioxolanyl group, or one phenyl, dihydrofuranone or furanone ring wherein each ring is optionally substituted with any combination of one to three halogen atoms, one to three Cι~C₄-alkyl groups, one to three Cι-C₄-haloalkyl groups , one to three Cι~C₄-alkoxy groups or one to three Cι-C₄-haloalkoxy groups, C₃-C₆-alkenyl optionally substituted with one

Cι-C₆-alkoxy, COOR³², C(0)R³³ or C(OR³⁴)₂ group, C₃-C₆-alkynyl, phenyl optionally substituted with any combination of one to three halogen atoms, one or two Cι-C₄-alkyl groups, one or two Cχ-C₄~alkoxy groups, one Cι-C₄-haloalkyl group, one C]_-C₄-haloalkoxy group, one cyano group, one nitro group, one NR³⁹R⁴⁰ group or one C(0)R³³ group, or benzyl optionally substituted on the phenyl ring with any combination of one to three halogen atoms, one or two Cι-C₄~alkyl groups, one or two Ci~C₄-alkoxy groups, one Cι-C₄-haloalkyl group, one Cι-C₄-haloalkoxy group, one cyano group, one nitro group, one NR³⁹R⁴⁰ group or one C(0)R³³ group; R²³ is hydrogen or C₁-C₄-alkyl ;

R²⁸ is halogen;

^R29 is hydrogen, Cι-C₄-alkyl or Cι-C₄-haloalkyl; R³² is hydrogen, Si(R⁴⁷)₃, Cι-C₄-alkyl optionally substituted with one COOR⁴⁸,

OC(0)R³³ or Cι-C -alkoxy group, Cι-C₄-haloalkyl , C₃-Cs-cycloalkyl , C₃-C₈-halocycloalkyl , C₃-C₆-alkenyl optionally substituted with one phenyl group,

C₃-C₆-haloalkenyl , Cs-C_δ-cycloalkenyl , C₅-C₈-halocycloalkenyl , C₃-C₆-alkynyl optionally substituted with one phenyl group,

C₃-C₆-haloalkynyl , benzyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, Cι-C -alkyl, Cι-C₄-haloalkyl , Cι-C₄-alkoxy and

Cι-C₄-haloalkoxy groups, phenyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, Cι-C₄-alkyl, Cι-C -haloalkyl , Ci^-alkoxy and Cι-C₄~haloalkoxy groups,

Cι~C₄-alkyl substituted with one pyridyl, furyl, thienyl, tetrahydrofuryl or NR⁴⁹R⁵⁰ group, or an alkali metal, alkaline earth metal, manganese, copper, zinc, cobalt, silver, nickel, ammonium or organic ammonium cation;

R³⁴, R³⁷ and R³⁸ are each independently Ci-Cβ-alkyl;

R³⁵ and R⁴⁹ are each independently hydrogen or Cι-C₄-alkyl and R³⁶ and R⁵⁰ are each independently hydrogen, cyano, Cι~C₄-alkyl, S0R⁵¹ or phenyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, Cι-C₄~alkyl, Cι-C₄-haloalkyl, Cι-C₄~alkoxy and Cι-C₄~haloalkoxy groups, or when R³⁵ and R³⁶ or R⁴⁹ and R⁵⁰ are taken together with the nitrogen atom to which they are attached, they form a 5- to 12-membered monocyclic or fused bicyclic, heterocyclic ring optionally substituted with one or more groups independently selected from halogen, cyano, nitro, amino, hydroxyl, C_l- -alkyl, Cι-C₄-haloalkyl, Cχ-C₄-alkoxy, Cι-C₄-haloalkoxy or Cι-C₄-haloalkylsulfonyl groups;

R³⁹, R⁴⁰, R⁴², R⁴³, R⁴⁶ and R⁴⁸ are each independently hydrogen, C₂-C₆-alkenyl, C₃-C₈-cycloalkyl, Ci-Cs-alkyl optionally substituted with one or two Cι~C₄-alkoxy groups, benzyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, Cι-C₄-alkyl, Cι-C₄-haloalkyl, Cχ-C₄-alkoxy and Cι-C₄-haloalkoxy groups, or phenyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro,

Cι-C₄-alkyl, Cι-C₄-haloalkyl, Cχ-C₄-alkoxy and Cι-C -haloalkoxy groups, and when R⁴⁶ and R⁴⁸ are taken together with the atom to which they are attached, they form a 5- to 12-membered monocyclic or fused bicyclic, heterocyclic or cycloalkyl ring optionally substituted with one or more groups independently selected from halogen, cyano, nitro, amino, hydroxyl, Cι-C₄-alkyl, Cι-C₄-haloalkyl, Ci-C₄~alkoxy, Cι~C₄-haloalkoxy or C -C₄-haloalkylsulfonyl groups;

R⁴¹ and R⁴⁷ are each independently Cι-C₄-alkyl, benzyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, Cι-C₄-alkyl, Cx^-haloalkyl, Cι-C₄~alkoxy and

Cι~C₄-haloalkoxy groups, or phenyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, Cχ-C₄-alkyl, Cι-C₄~haloalkyl , Cι-C₄-alkoxy and Cι~C₄-haloalkoxy groups;

X¹ and X² are each independently oxygen or sulfur; q is an integer of 0, 1 or 2 ; and the optical isomers, diastereomers and/or tautomers thereof; and an adjuvant.

1. The method of claim 11, wherein formula (I) :

X is oxygen;

Alk is methyl; R is trifluormethyl;

R¹ is hydrogen;

R² is hydrogen or fluorine;

Y is R¹², COOR¹⁹, C(0)R¹⁴ or C(0)NR¹³R¹⁴;

R¹² is hydrogen,

Ci-Cβ-alkyl optionally substituted with any combination of one to three halogen atoms, one hydroxyl group, one or two Cι-C₄~alkoxy groups, one Cχ-C₄-haloalkoxy group, one S0₂R¹⁷ group, one or two cyano groups, one C(0)R¹⁸ group, one or two COOR¹⁹ groups, one or two C(O)NR²⁰R²¹ groups, one P(0) (OR²³) ₂ group or one OC(0)R³³ group, C₂-C₆-alkenyl optionally substituted with any combination of one C(0)R¹⁸ group or one COOR¹⁹ group,

_OCR56_R57_COOR32 _OCR56_R57_C(0)_NR35_R36

R¹³ is hydrogen, Cι-C₄-alkyl or S0₂R⁵¹ ; R¹⁴ is hydrogen, Cχ-C₄-alkyl or benzyl ; R¹⁸, R²³, R⁵⁶ and R⁵⁷ are each independently hydrogen or

Cι-C₃-alkyl; R⁵², R⁵³, R⁵⁴ and R⁵⁵ are each independently hydrogen,

C₁-C₃-alkyl, C₂-C₃-alkenyl, Cι-C₃~alkoxy or halogen, pro- vided that at least one of R⁵² , R⁵³ , R⁵⁴ and R⁵⁵ is hydrogen; R¹⁹ is hydrogen, C₁-C₄-alkyl, Cs-Cς-alkenyl , C₃-C₆-alkynyl, benzyl, pyridyl or an alkali metal, alkaline earth metal, ammonium or organic ammonium cation; R²² is hydrogen, C(0)R³³, S0₂R⁴⁷, Cι-C₄-alkyl optionally substituted with one cyano group, C₃-C₆-alkenyl or C₃-C₆-al- kynyl ; R³² is hydrogen,

Cι~C₄-alkyl optionally substituted with one COOR⁴⁸ or Cι-C₄-alkoxy group,

Cι-C -haloalkyl ,

C₃-C₆-alkenyl optionally substituted with one phenyl group ,

C₃-C₆-alkynyl optionally substituted with one phenyl group,

Cι-C₄~alkyl substituted with one pyridyl, furyl, thienyl, tetrahydrofuryl or NR⁴⁹R⁵⁰ group, or an alkali metal, alkaline earth metal, ammonium or organic ammonium cation; R²⁵ and R⁴⁹ are each independently hydrogen or Cι~C₄-alkyl; R³⁶ is S0₂R⁵¹ or Cι-C₃-alkoxy; R¹⁷, R³³ and R⁵¹ are each independently Cι-C₄-alkyl,

Cχ-C₄-haloalkyl, NR⁴⁶R⁴⁸, C -C₆-cycloalkyl or an isoxazole ring; R46 _{anG R}48 _are each independently hydrogen, Cι-C₄-alkyl or benzyl ; R⁴⁷ is C₁-C₄-alkyl;

R⁵⁰ is Cι-C₄-alkyl or phenyl optionally substituted with one or more groups independently selected from halogen, cyano, Cχ-C₄-alkyl, Cι-C₄-haloalkyl, Cι~C₄-alkoxy and Cι-C₄-haloalkoxy groups.

12. The method of claim 10, wherein formula (I):

Y is Cι-C₃-alkyl, COOR³², halomethyl, cyanomethyl, C(CH₃)₂-COOR³², Cι-C₃-alkoxyethyl, Ci-Cs-alkoxymethyl, hydroxy- methyl, CHO, C(0)CH₃, CH (CH₃) (Ci^-alkoxy) , C(CH₃)₂-CN, CH[0(Cι-C₃-alkyl) ]₂, CH₂-S0₂R¹⁷, C (0)NHS0₂R⁵¹,

_R22 is cyanomethyl, methyl, ethyl, allyl or propargyl; _R32 is hydrogen, Cι-C₄~alkyl optionally substituted with one

COOR⁴⁸ group, Cι-C -haloalkyl , C₃-C₆-alkenyl or C₃-C₆-alky- nyl ; and

R³5 is hydrogen.

13. The method of claim 10, wherein the adjuvant is methylated vegetable oil, methylated crop oil, methylated seed oil, a surfactant, or mixtures thereof.

14. The method of claim 10, wherein the benzisothiazole or benzisoxazole compound of formula (I) is applied at a rate from about 0.1 g/ha to about 500 g/ha.

15. The method of claim 10, wherein the benzisothiazole or benzisoxazole compound of formula (I) is applied at a rate from about 1.0 g/ha to about 100 g/ha.

16. The method of claim 10, wherein the composition is formulated into a suspension concentrate.

17. The method of claim 16, wherein the concentration of benziso- thiazole or benzisoxazole compound of formula (I) is from about 50 g/1 to about 250 g/1.

18. The method of claim 16, wherein the composition is sprayed onto the plant 0 days, 1 day, 2 days, 7 days or 14 days be- fore cutting the plant.